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#\#CIF_1.0 ################################################################################ # # # This CIF is a part of the B-IncStrDB # # (Bilbao Incommensurate Structures Database) # # http://www.cryst.ehu.eus/bincstrdb/ # # # # Please note that the structure of the CIF file may differ from the one # # deposited, as it may have been modified to comply with the standard. The # # file has been validated against official dictionaries as well as local # # dictionaries including non-standard data names used by SHELXL (Sheldrick, # # G. M. (2008). Acta Cryst. A 64, 112-122) and JANA (Petricek, V., Dusek, M. # # and Palatinus, L. (2014), Z. Kristallogr. 229, 345-352). # # # # For comments and/or criticisms, please e-mail to administrador-bcs@ehu.es # # # ################################################################################ data_global _publ_contact_author_name 'Gagor, Anna' _publ_contact_author_address ;Department of Crystallography Institute of Low Temperature and Structure Research PAS, Okolna 2, Wroclaw Poland ; _publ_contact_author_email a.gagor@int.pan.wroc.pl loop_ _publ_author_name _publ_author_address 'Gagor, Anna' ;Department of Crystallography Institute of Low Temperature and Structure Research PAS, Okolna 2, Wroclaw Poland ; _publ_section_title ;Phase transitions in ferroelectric 4-aminopyridinium tetrachloroantimonate(III) - revisited ; _journal_date_recd_electronic 2017-10-18 _journal_date_accepted 2018-03-02 _journal_coeditor_code DK5062SUP1 _journal_paper_category FA _journal_techeditor_code B180366 _iucr_compatibility_tag ACTA95 _journal_name_full 'Acta Crystallographica Section B' _journal_volume 74 _journal_year 2018 _journal_page_first 217 _journal_page_last 225 _journal_paper_doi https://doi.org/10.1107/S2052520618003669 data_I _chemical_formula_sum 'C5 H7 Cl4 N2 Sb1' _chemical_formula_weight 358.7 _chemical_absolute_configuration ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' _space_group_IT_number 15 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,y,-z+1/2 3 -x,-y,-z 4 x,-y,z+1/2 5 x+1/2,y+1/2,z 6 -x+1/2,y+1/2,-z+1/2 7 -x+1/2,-y+1/2,-z 8 x+1/2,-y+1/2,z+1/2 _cell_length_a 13.4747(4) _cell_length_b 12.9393(4) _cell_length_c 7.7611(2) _cell_angle_alpha 90 _cell_angle_beta 123.733(2) _cell_angle_gamma 90 _cell_volume 1125.34(6) _cell_formula_units_Z 4 _cell_measurement_temperature 320.03(16) _cell_measurement_reflns_used 5267 _cell_measurement_theta_min 3.2470 _cell_measurement_theta_max 29.1660 _exptl_crystal_type_of_structure cryst _exptl_crystal_density_diffrn 2.1171 _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.353 _exptl_crystal_description prism _exptl_crystal_size_max 0.233 _exptl_crystal_size_mid 0.162 _exptl_crystal_size_min 0.101 _exptl_absorpt_correction_T_min 0.85221 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _diffrn_ambient_temperature 320.03(16) _diffrn_ambient_environment air _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas' _diffrn_detector 'CCD plate' _diffrn_detector_type Atlas _diffrn_detector_area_resol_mean 10.6249 _diffrn_reflns_number 7260 _diffrn_reflns_theta_min 2.4 _diffrn_reflns_theta_max 29.44 _diffrn_reflns_theta_full 27.79 _diffrn_measured_fraction_theta_max 0.91 _diffrn_measured_fraction_theta_full 0.98 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_unetI/netI 0.0101 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_radiation_probe x-ray _reflns_number_total 1419 _reflns_number_gt 1295 _reflns_threshold_expression I>3\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_gt 0.0944 _refine_ls_R_factor_all 0.0295 _refine_ls_wR_factor_ref 0.0944 _refine_ls_goodness_of_fit_ref 1.95 _refine_ls_goodness_of_fit_gt 1.95 _refine_ls_number_reflns 1295 _refine_ls_number_parameters 39 _refine_ls_number_restraints 13 _refine_ls_weighting_scheme sigma _refine_ls_weighting_details w=1/(\s^2^(I)+0.0016I^2^) _refine_ls_shift/su_max 0.0287 _refine_ls_shift/su_mean 0.0041 _refine_diff_density_max 0.84 _refine_diff_density_min -0.56 _refine_ls_extinction_method none _refine_ls_hydrogen_treatment constr loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' Cl 0.1484 0.1585 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' Sb -0.5866 1.5461 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' _audit_creation_method 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' #loop_ # _restr_distance_atom_site_label_1 # _restr_distance_site_symmetry_1 # _restr_distance_atom_site_label_2 # _restr_distance_site_symmetry_2 # _restr_distance_target # _restr_distance_target_weight_param # N ? C4 ? 1.45 0.01 # N1 ? C2 ? 1.4 0.01 # C2 ? C3 ? 1.4 0.01 # C3 ? C4 ? 1.4 0.01 # C4 ? C5 ? 1.4 0.01 # C5 ? C6 ? 1.4 0.01 # C6 ? N1 ? 1.4 0.01 #loop_ # _restr_angle_atom_site_label_1 # _restr_angle_atom_site_label_2 # _restr_angle_atom_site_label_3 # _restr_angle_target # _restr_angle_target_weight_param # N1 C2 C3 120 1 # C2 C3 C4 120 1 # C3 C4 C5 120 1 # C4 C5 C6 120 1 # C5 C6 N1 120 1 # C6 N1 C2 120 1 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_adp_type _atom_site_U_iso_or_equiv _atom_site_site_symmetry_multiplicity _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_disorder_assembly _atom_site_disorder_group Sb Sb 0.5 0.57454(2) 0.75 Uani 0.04426(19) 4 1 d ? ? ? Cl1 Cl 0.37927(11) 0.70152(10) 0.4950(2) Uani 0.0784(6) 8 1 d ? ? ? Cl2 Cl 0.64928(10) 0.58102(8) 0.6295(2) Uani 0.0647(5) 8 1 d ? ? ? Na N 0.1597(8) 0.6524(10) 0.0512(15) Uani 0.099(4) 8 0.5 d ? ? ? N1a N -0.1256(8) 0.5220(7) -0.4734(14) Uani 0.099(4) 8 0.5 d ? ? ? C2a C -0.0378(9) 0.4598(7) -0.3230(17) Uani 0.099(4) 8 0.5 d ? ? ? C3a C 0.0607(9) 0.5040(8) -0.1533(17) Uani 0.099(4) 8 0.5 d ? ? ? C4a C 0.0638(7) 0.6117(8) -0.1316(15) Uani 0.099(4) 8 0.5 d ? ? ? C5a C -0.0249(9) 0.6775(7) -0.2815(18) Uani 0.099(4) 8 0.5 d ? ? ? C6a C -0.1179(9) 0.6290(7) -0.4571(16) Uani 0.099(4) 8 0.5 d ? ? ? H1n1a H -0.187525 0.493855 -0.581753 Uiso 0.1183 8 0.5 d ? ? ? H1c3a H 0.126061 0.462108 -0.051507 Uiso 0.1183 8 0.5 d ? ? ? H1c5a H -0.02161 0.751086 -0.2639 Uiso 0.1183 8 0.5 d ? ? ? H1c2a H -0.0452 0.3859 -0.3362 Uiso 0.1183 8 0.5 d ? ? ? H1c6a H -0.1782 0.6703 -0.5697 Uiso 0.1183 8 0.5 d ? ? ? H1na H 0.2149 0.6116 0.1444 Uiso 0.1183 8 0.5 d ? ? ? H2na H 0.1647 0.7188 0.0727 Uiso 0.1183 8 0.5 d ? ? ? loop_ _atom_site_aniso_label _atom_site_aniso_type_symbol _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Sb Sb 0.0434(2) 0.0487(2) 0.0417(2) 0 0.02426(16) 0 Cl1 Cl 0.0731(6) 0.0751(7) 0.0876(7) 0.0245(5) 0.0450(6) 0.0343(6) Cl2 Cl 0.0505(5) 0.0800(7) 0.0650(6) -0.0007(4) 0.0330(5) -0.0027(4) Na N 0.104(4) 0.122(4) 0.109(4) -0.030(3) 0.084(4) -0.037(3) N1a N 0.104(4) 0.122(4) 0.109(4) -0.030(3) 0.084(4) -0.037(3) C2a C 0.104(4) 0.122(4) 0.109(4) -0.030(3) 0.084(4) -0.037(3) C3a C 0.104(4) 0.122(4) 0.109(4) -0.030(3) 0.084(4) -0.037(3) C4a C 0.104(4) 0.122(4) 0.109(4) -0.030(3) 0.084(4) -0.037(3) C5a C 0.104(4) 0.122(4) 0.109(4) -0.030(3) 0.084(4) -0.037(3) C6a C 0.104(4) 0.122(4) 0.109(4) -0.030(3) 0.084(4) -0.037(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Sb Cl1 ? ? 2.3848(12) ? Sb Cl1 ? 2_656 2.3848(12) ? Sb Cl2 ? ? 2.6488(18) ? Sb Cl2 ? 2_656 2.6488(18) ? Sb Cl2 ? 3_666 3.1927(11) ? Sb Cl2 ? 4_565 3.1927(11) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1 Sb Cl1 ? ? 2_656 92.90(4) ? Cl1 Sb Cl2 ? ? ? 89.26(5) ? Cl1 Sb Cl2 ? ? 2_656 88.24(5) ? Cl1 Sb Cl2 ? ? 3_666 83.04(4) ? Cl1 Sb Cl2 ? ? 4_565 171.87(5) ? Cl1 Sb Cl2 2_656 ? ? 88.24(5) ? Cl1 Sb Cl2 2_656 ? 2_656 89.26(5) ? Cl1 Sb Cl2 2_656 ? 3_666 171.87(5) ? Cl1 Sb Cl2 2_656 ? 4_565 83.04(4) ? Cl2 Sb Cl2 ? ? 2_656 176.37(3) ? Cl2 Sb Cl2 ? ? 3_666 84.67(4) ? Cl2 Sb Cl2 ? ? 4_565 97.63(4) ? Cl2 Sb Cl2 2_656 ? 3_666 97.63(4) ? Cl2 Sb Cl2 2_656 ? 4_565 84.67(4) ? Cl2 Sb Cl2 3_666 ? 4_565 101.83(3) ? data_II _journal_date_recd_electronic 2017-10-18 _journal_date_accepted 2018-03-02 _journal_coeditor_code DK5062SUP1 _journal_paper_category FA _journal_techeditor_code B180366 _iucr_compatibility_tag ACTA95 _chemical_formula_sum 'C5 H7 Cl4 N2 Sb1' _chemical_formula_weight 358.69 _chemical_absolute_configuration ? _space_group_crystal_system monoclinic _space_group_ssg_name C2/c(0\b0)s0 loop_ _space_group_symop_ssg_id _space_group_symop_ssg_operation_algebraic 1 x1,x2,x3,x4 2 -x1,x2,-x3+1/2,x4+1/2 3 -x1,-x2,-x3,-x4 4 x1,-x2,x3+1/2,-x4+1/2 5 x1+1/2,x2+1/2,x3,x4 6 -x1+1/2,x2+1/2,-x3+1/2,x4+1/2 7 -x1+1/2,-x2+1/2,-x3,-x4 8 x1+1/2,-x2+1/2,x3+1/2,-x4+1/2 _cell_length_a 13.3923 _cell_length_b 12.815 _cell_length_c 7.8256 _cell_angle_alpha 90 _cell_angle_beta 123.735 _cell_angle_gamma 90 _cell_volume 1116.899 _cell_modulation_dimension 1 loop_ _cell_wave_vector_seq_id _cell_wave_vector_x _cell_wave_vector_y _cell_wave_vector_z 1 0.000000 0.586000 0.000000 _cell_formula_units_Z 4 _cell_measurement_reflns_used 9808 _cell_measurement_theta_min 3.2460 _cell_measurement_theta_max 29.1240 _cell_measurement_temperature 290.00(11) _exptl_crystal_type_of_structure mod _exptl_crystal_density_diffrn 2.0911 _exptl_crystal_F_000 680 _exptl_crystal_description prism _exptl_crystal_size_max 0.233 _exptl_crystal_size_mid 0.162 _exptl_crystal_size_min 0.101 _exptl_absorpt_coefficient_mu 3.378 _exptl_absorpt_correction_T_min 0.83997 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -3 -18 1 0.0687 3 18 -1 0.0705 13 -2 2 0.0529 -13 2 -2 0.0520 18 -2 -9 0.0798 -17 2 10 0.0859 -4 0 10 0.1187 18 -3 -3 0.0389 7 15 -6 0.0805 -13 9 0 0.0608 13 8 1 0.0547 -14 -7 -1 0.0455 3 -17 -4 0.1040 _diffrn_ambient_temperature 290.00(11) _diffrn_ambient_environment air _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas' _diffrn_detector 'CCD plate' _diffrn_detector_type Atlas _diffrn_detector_area_resol_mean 10.6249 _diffrn_reflns_number 21939 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 29.43 _diffrn_reflns_theta_full 27.9 _diffrn_measured_fraction_theta_max 0.91 _diffrn_measured_fraction_theta_full 0.98 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_unetI/netI 0.0134 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_index_m_1_min -1 _diffrn_reflns_limit_index_m_1_max 1 _diffrn_radiation_probe x-ray _reflns_number_total 4209 _reflns_number_gt 2539 _reflns_threshold_expression I>3\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_gt 0.0945 _refine_ls_R_factor_all 0.0274 _refine_ls_wR_factor_ref 0.0945 _refine_ls_goodness_of_fit_ref 1.82 _refine_ls_goodness_of_fit_gt 1.82 _refine_ls_number_reflns 2539 _refine_ls_number_parameters 133 _refine_ls_number_constraints 28 _refine_ls_weighting_scheme sigma _refine_ls_weighting_details w=1/(\s^2^(I)+0.0016I^2^) _refine_ls_hydrogen_treatment constr _refine_ls_shift/su_max 0.0491 _refine_ls_shift/su_mean 0.0087 _refine_diff_density_max 0.52 _refine_diff_density_min -0.71 _refine_ls_extinction_method none loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' Cl 0.1484 0.1585 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' Sb -0.5866 1.5461 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' _audit_creation_method 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_adp_type _atom_site_U_iso_or_equiv _atom_site_site_symmetry_multiplicity _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.5 0.573560(18) 0.75 Uani 0.03484(16) 4 1 d ? ? ? Cl2 Cl 0.37993(7) 0.70182(7) 0.49724(13) Uani 0.0598(4) 8 1 d ? ? ? Cl3 Cl 0.65132(7) 0.58010(6) 0.63310(14) Uani 0.0515(4) 8 1 d ? ? ? Naa N 0.1529(8) 0.6567(7) 0.0376(13) Uani 0.075(3) 8 0.5 d ? ? ? C3aa C -0.0255(10) 0.6792(10) -0.2875(17) Uani 0.053(4) 8 0.5 d ? ? ? C2aa C -0.1162(12) 0.6301(14) -0.455(2) Uani 0.083(5) 8 0.4964 d ? ? ? N1aa N -0.1272(13) 0.5277(13) -0.477(2) Uani 0.101(4) 8 0.5 d ? ? ? C6aa C -0.0440(15) 0.4658(11) -0.327(3) Uani 0.083(5) 8 0.5 d ? ? ? C5aa C 0.0521(13) 0.5063(9) -0.151(2) Uani 0.067(4) 8 0.5 d ? ? ? C4aa C 0.0613(10) 0.6123(7) -0.1310(17) Uani 0.052(3) 8 0.5 d ? ? ? H1naa H 0.201224 0.618743 0.144936 Uiso 0.0896 8 0.5 d ? ? ? H2naa H 0.164406 0.723652 0.040527 Uiso 0.0896 8 0.5 d ? ? ? H1c3aa H -0.020035 0.753805 -0.275539 Uiso 0.0641 8 0.5 d ? ? ? H1c2aa H -0.177153 0.672471 -0.564569 Uiso 0.0996 8 0.5 d ? ? ? H1c6aa H -0.052276 0.391434 -0.344508 Uiso 0.1 8 0.5 d ? ? ? H1c5aa H 0.111394 0.461602 -0.043598 Uiso 0.0806 8 0.5 d ? ? ? H1n1aa H -0.187995 0.500705 -0.589147 Uiso 0.1208 8 0.5 d ? ? ? loop_ _atom_site_aniso_label _atom_site_aniso_type_symbol _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Sb1 Sb 0.03412(19) 0.0376(2) 0.03173(19) 0 0.01759(14) 0 Cl2 Cl 0.0560(5) 0.0570(5) 0.0613(5) 0.0162(3) 0.0294(4) 0.0223(4) Cl3 Cl 0.0419(4) 0.0597(5) 0.0528(5) -0.0001(3) 0.0262(4) -0.0026(3) Naa N 0.061(3) 0.092(4) 0.065(3) -0.005(3) 0.031(3) -0.016(3) C3aa C 0.056(4) 0.063(4) 0.049(4) 0.000(2) 0.034(3) 0.002(2) C2aa C 0.077(5) 0.120(6) 0.072(5) 0.000(5) 0.053(5) -0.014(5) N1aa N 0.057(4) 0.194(8) 0.065(4) -0.051(4) 0.043(3) -0.063(4) C6aa C 0.108(6) 0.085(5) 0.102(5) -0.029(5) 0.086(5) -0.025(5) C5aa C 0.089(4) 0.046(3) 0.084(4) 0.000(3) 0.059(4) -0.008(3) C4aa C 0.054(3) 0.059(3) 0.058(3) -0.002(3) 0.041(3) -0.006(3) loop_ _atom_site_Fourier_wave_vector_seq_id _jana_atom_site_Fourier_wave_vector_q1_coeff 1 1 loop_ _jana_atom_site_occ_Fourier_absolute_site_label _jana_atom_site_occ_Fourier_absolute Naa 1 C3aa 1 C2aa 1 N1aa 1 C6aa 1 C5aa 1 C4aa 1 H1naa 1 H2naa 1 H1c3aa 1 H1c2aa 1 H1c6aa 1 H1c5aa 1 H1n1aa 1 loop_ _atom_site_occ_Fourier_id _atom_site_occ_Fourier_atom_site_label _atom_site_occ_Fourier_wave_vector_seq_id Naao1 Naa 1 C3aao1 C3aa 1 C2aao1 C2aa 1 N1aao1 N1aa 1 C6aao1 C6aa 1 C5aao1 C5aa 1 C4aao1 C4aa 1 H1naao1 H1naa 1 H2naao1 H2naa 1 H1c3aao1 H1c3aa 1 H1c2aao1 H1c2aa 1 H1c6aao1 H1c6aa 1 H1c5aao1 H1c5aa 1 H1n1aao1 H1n1aa 1 loop_ _atom_site_occ_Fourier_param_id _atom_site_occ_Fourier_param_cos _atom_site_occ_Fourier_param_sin Naao1 0.4471 0.7315 C3aao1 0.3851 0.7659 C2aao1 0.5165 0.6843 N1aao1 0.732 0.4462 C6aao1 0.814 0.2691 C5aao1 0.765 0.387 C4aao1 0.5602 0.649 H1naao1 0.5446 0.6621 H2naao1 0.255 0.8185 H1c3aao1 0.1628 0.8417 H1c2aao1 0.4038 0.7562 H1c6aao1 0.8564 0.039 H1c5aao1 0.818 0.2565 H1n1aao1 0.7727 0.3713 loop_ _atom_site_displace_Fourier_id _atom_site_displace_Fourier_atom_site_label _atom_site_displace_Fourier_axis _atom_site_displace_Fourier_wave_vector_seq_id Sb1x1 Sb1 x 1 Sb1y1 Sb1 y 1 Sb1z1 Sb1 z 1 Cl2x1 Cl2 x 1 Cl2y1 Cl2 y 1 Cl2z1 Cl2 z 1 Cl3x1 Cl3 x 1 Cl3y1 Cl3 y 1 Cl3z1 Cl3 z 1 Naax1 Naa x 1 Naay1 Naa y 1 Naaz1 Naa z 1 C3aax1 C3aa x 1 C3aay1 C3aa y 1 C3aaz1 C3aa z 1 C2aax1 C2aa x 1 C2aay1 C2aa y 1 C2aaz1 C2aa z 1 N1aax1 N1aa x 1 N1aay1 N1aa y 1 N1aaz1 N1aa z 1 C6aax1 C6aa x 1 C6aay1 C6aa y 1 C6aaz1 C6aa z 1 C5aax1 C5aa x 1 C5aay1 C5aa y 1 C5aaz1 C5aa z 1 C4aax1 C4aa x 1 C4aay1 C4aa y 1 C4aaz1 C4aa z 1 H1naax1 H1naa x 1 H1naay1 H1naa y 1 H1naaz1 H1naa z 1 H2naax1 H2naa x 1 H2naay1 H2naa y 1 H2naaz1 H2naa z 1 H1c3aax1 H1c3aa x 1 H1c3aay1 H1c3aa y 1 H1c3aaz1 H1c3aa z 1 H1c2aax1 H1c2aa x 1 H1c2aay1 H1c2aa y 1 H1c2aaz1 H1c2aa z 1 H1c6aax1 H1c6aa x 1 H1c6aay1 H1c6aa y 1 H1c6aaz1 H1c6aa z 1 H1c5aax1 H1c5aa x 1 H1c5aay1 H1c5aa y 1 H1c5aaz1 H1c5aa z 1 H1n1aax1 H1n1aa x 1 H1n1aay1 H1n1aa y 1 H1n1aaz1 H1n1aa z 1 loop_ _atom_site_displace_Fourier_param_id _atom_site_displace_Fourier_param_cos _atom_site_displace_Fourier_param_sin Sb1x1 0.00266(2) 0.01535(3) Sb1y1 0 0 Sb1z1 0.00010(3) 0.02229(5) Cl2x1 -0.00205(8) 0.02215(9) Cl2y1 -0.00081(6) 0.00825(6) Cl2z1 -0.01454(13) 0.03541(15) Cl3x1 0.00193(6) 0.01413(8) Cl3y1 -0.00741(6) 0.00486(6) Cl3z1 0.00009(10) 0.01498(12) Naax1 -0.0036(11) 0.0161(14) Naay1 -0.0104(10) -0.0045(14) Naaz1 -0.0008(13) 0.0215(17) C3aax1 -0.0028(16) 0.017(2) C3aay1 0.0014(15) 0.000(2) C3aaz1 -0.0010(17) 0.021(2) C2aax1 -0.003(2) 0.017(2) C2aay1 0.0077(18) 0.002(3) C2aaz1 -0.003(2) 0.019(3) N1aax1 -0.003(2) 0.018(3) N1aay1 0.009(2) -0.001(2) N1aaz1 -0.008(3) 0.020(3) C6aax1 -0.004(2) 0.020(2) C6aay1 0.0025(17) -0.0014(18) C6aaz1 -0.010(3) 0.024(3) C5aax1 -0.0045(17) 0.0181(19) C5aay1 -0.0041(13) 0.0003(15) C5aaz1 -0.008(2) 0.021(2) C4aax1 -0.0036(13) 0.0163(16) C4aay1 -0.0046(11) -0.0014(15) C4aaz1 -0.0030(13) 0.0197(17) H1naax1 -0.0043(11) 0.0157(13) H1naay1 -0.0147(10) -0.0039(14) H1naaz1 -0.0020(15) 0.0205(19) H2naax1 -0.0034(12) 0.0175(15) H2naay1 -0.0094(11) -0.0071(14) H2naaz1 0.0006(16) 0.026(2) H1c3aax1 -0.0033(18) 0.019(2) H1c3aay1 0.0010(15) 0.0002(19) H1c3aaz1 0.000(2) 0.026(2) H1c2aax1 -0.002(2) 0.018(3) H1c2aay1 0.011(2) 0.005(3) H1c2aaz1 -0.002(3) 0.020(3) H1c6aax1 -0.003(3) 0.023(3) H1c6aay1 0.0025(19) -0.0024(17) H1c6aaz1 -0.011(4) 0.031(4) H1c5aax1 -0.0047(18) 0.0198(19) H1c5aay1 -0.0079(12) 0.0024(13) H1c5aaz1 -0.009(3) 0.024(3) H1n1aax1 -0.003(3) 0.019(3) H1n1aay1 0.013(2) -0.003(3) H1n1aaz1 -0.010(3) 0.021(4) loop_ _atom_site_U_Fourier_id _atom_site_U_Fourier_atom_site_label _atom_site_U_Fourier_tens_elem _atom_site_U_Fourier_wave_vector_seq_id Sb1U111 Sb1 U11 1 Sb1U221 Sb1 U22 1 Sb1U331 Sb1 U33 1 Sb1U121 Sb1 U12 1 Sb1U131 Sb1 U13 1 Sb1U231 Sb1 U23 1 Cl2U111 Cl2 U11 1 Cl2U221 Cl2 U22 1 Cl2U331 Cl2 U33 1 Cl2U121 Cl2 U12 1 Cl2U131 Cl2 U13 1 Cl2U231 Cl2 U23 1 loop_ _atom_site_U_Fourier_param_id _atom_site_U_Fourier_param_cos _atom_site_U_Fourier_param_sin Sb1U111 0 0 Sb1U221 0 0 Sb1U331 0 0 Sb1U121 0.00002(11) 0.00100(12) Sb1U131 0 0 Sb1U231 0.00096(11) 0.00157(11) Cl2U111 0.0014(5) 0.0018(6) Cl2U221 -0.0063(5) 0.0002(5) Cl2U331 -0.0029(6) 0.0048(6) Cl2U121 -0.0054(4) 0.0025(5) Cl2U131 -0.0014(5) 0.0036(5) Cl2U231 -0.0034(4) 0.0047(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_ssg_symmetry_1 _geom_bond_site_ssg_symmetry_2 _geom_bond_distance_av _geom_bond_distance_min _geom_bond_distance_max _geom_bond_publ_flag Sb1 Cl2 ? ? 2.3833(11) 2.3796(12) 2.3886(12) ? Sb1 Cl2 ? 2_6565 2.3833(11) 2.3796(12) 2.3886(12) ? Sb1 Cl3 ? ? 2.6493(17) 2.6179(18) 2.6810(18) ? Sb1 Cl3 ? 2_6565 2.6487(17) 2.6179(18) 2.6810(18) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_ssg_symmetry_1 _geom_angle_site_ssg_symmetry_2 _geom_angle_site_ssg_symmetry_3 _geom_angle_av _geom_angle_min _geom_angle_max _geom_angle_publ_flag Cl2 Sb1 Cl2 ? ? 2_6565 92.64(4) 92.63(4) 92.66(4) ? Cl2 Sb1 Cl3 ? ? ? 89.12(5) 88.09(5) 90.12(5) ? Cl2 Sb1 Cl3 ? ? 2_6565 88.42(5) 87.98(5) 88.92(5) ? Cl2 Sb1 Cl3 2_6565 ? ? 88.42(5) 87.98(5) 88.92(5) ? Cl2 Sb1 Cl3 2_6565 ? 2_6565 89.14(5) 88.09(5) 90.12(5) ? Cl3 Sb1 Cl3 ? ? 2_6565 176.18(3) 175.98(3) 176.39(3) ? data_III _journal_date_recd_electronic 2017-10-18 _journal_date_accepted 2018-03-02 _journal_coeditor_code DK5062SUP1 _journal_paper_category FA _journal_techeditor_code B180366 _iucr_compatibility_tag ACTA95 _chemical_formula_sum 'C5 H7 Cl4 N2 Sb1' _chemical_formula_weight 358.69 _space_group_crystal_system monoclinic _space_group_ssg_name Cc(0\b0)0 loop_ _space_group_symop_ssg_id _space_group_symop_ssg_operation_algebraic 1 x1,x2,x3,x4 2 x1,-x2,x3+1/2,-x4 3 x1+1/2,x2+1/2,x3,x4 4 x1+1/2,-x2+1/2,x3+1/2,-x4 _cell_length_a 13.33(2) _cell_length_b 12.690(9) _cell_length_c 7.87(2) _cell_angle_alpha 90 _cell_angle_beta 123.8(2) _cell_angle_gamma 90 _cell_volume 1106(3) _cell_modulation_dimension 1 loop_ _cell_wave_vector_seq_id _cell_wave_vector_x _cell_wave_vector_y _cell_wave_vector_z 1 0.000000 0.666667 0.000000 _jana_cell_commen_supercell_matrix_1_1 1 _jana_cell_commen_supercell_matrix_2_2 3 _jana_cell_commen_supercell_matrix_3_3 1 _cell_formula_units_Z 4 _cell_measurement_temperature 260.00(12) _cell_measurement_reflns_used 11628 _cell_measurement_theta_min 3.2330 _cell_measurement_theta_max 29.1280 _exptl_crystal_type_of_structure mod _exptl_crystal_density_diffrn 2.157 _exptl_crystal_F_000 675 _exptl_absorpt_coefficient_mu 3.417 _exptl_crystal_description prism _exptl_crystal_size_max 0.233 _exptl_crystal_size_mid 0.162 _exptl_crystal_size_min 0.101 _exptl_absorpt_correction_T_min 0.85784 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _diffrn_ambient_temperature 260.00(12) _diffrn_ambient_environment N~2~ _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas' _diffrn_detector 'CCD plate' _diffrn_detector_type Atlas _diffrn_detector_area_resol_mean 10.6249 _diffrn_reflns_number 21857 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 29.6 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_max 0.9 _diffrn_measured_fraction_theta_full 0.98 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_unetI/netI 0.0174 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_index_m_1_min -1 _diffrn_reflns_limit_index_m_1_max 1 _diffrn_radiation_probe x-ray _reflns_number_total 7836 _reflns_number_gt 5379 _reflns_threshold_expression I>3\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_gt 0.1205 _refine_ls_R_factor_all 0.0362 _refine_ls_wR_factor_ref 0.1205 _refine_ls_goodness_of_fit_ref 2.26 _refine_ls_goodness_of_fit_gt 2.26 _refine_ls_number_reflns 5379 _refine_ls_number_parameters 151 _refine_ls_number_restraints 20 _refine_ls_number_constraints 3 _refine_ls_weighting_scheme sigma _refine_ls_weighting_details w=1/(\s^2^(I)+0.0016I^2^) _refine_ls_hydrogen_treatment constr _refine_ls_shift/su_max 0.0294 _refine_ls_shift/su_mean 0.0577 _refine_diff_density_max 1.06 _refine_diff_density_min -0.84 _refine_ls_extinction_method 'B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)' _refine_ls_extinction_coef -320(140) _refine_ls_abs_structure_details '2585 of Friedel pairs used in the refinement' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' Cl 0.1484 0.1585 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' Sb -0.5866 1.5461 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' _audit_creation_method 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' #loop_ # _restr_distance_atom_site_label_1 # _restr_distance_site_symmetry_1 # _restr_distance_atom_site_label_2 # _restr_distance_site_symmetry_2 # _restr_distance_target # _restr_distance_target_weight_param # N1a ? C2a ? 1.4 0.01 # C2a ? C3a ? 1.4 0.01 # C3a ? C4a ? 1.4 0.01 # C4a ? C5a ? 1.4 0.01 # C5a ? C6a ? 1.4 0.01 # C6a ? N1a ? 1.4 0.01 # N1b ? C2b ? 1.4 0.01 # C2b ? C3b ? 1.4 0.01 # C3b ? C4b ? 1.4 0.01 # C4b ? C5b ? 1.4 0.01 # C5b ? C6b ? 1.4 0.01 # C6b ? N1b ? 1.4 0.01 # Nb ? C4b ? 1.45 0.01 # Na ? C4a ? 1.45 0.01 #loop_ # _restr_angle_atom_site_label_1 # _restr_angle_atom_site_label_2 # _restr_angle_atom_site_label_3 # _restr_angle_target # _restr_angle_target_weight_param # N1b C2b C3b 120 1 # C2b C3b C4b 120 1 # C3b C4b C5b 120 1 # C4b C5b C6b 120 1 # C5b C6b N1b 120 1 # C6b N1b C2b 120 1 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_adp_type _atom_site_U_iso_or_equiv _atom_site_site_symmetry_multiplicity _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_disorder_assembly _atom_site_disorder_group Sb Sb 0.52316(3) 0.572651(17) 0.71584(4) Uani 0.02826(14) 4 1 d ? ? ? Cl1a Cl 0.40429(13) 0.70193(12) 0.4637(2) Uani 0.0465(7) 4 1 d ? ? ? Cl1b Cl 0.64468(13) 0.70128(12) 0.96745(19) Uani 0.0461(7) 4 1 d ? ? ? Cl2a Cl 0.67566(14) 0.58027(12) 0.5982(2) Uani 0.0379(11) 4 1 d ? ? ? Cl2b Cl 0.37023(16) 0.57969(13) 0.8267(2) Uani 0.0459(13) 4 1 d ? ? ? Naa N 0.1844(3) 0.6582(4) 0.0154(4) Uani 0.0640(16) 4 0.6 d ? ? ? C5aa C 0.0097(8) 0.6799(7) -0.3078(11) Uani 0.0640(16) 4 0.6 d ? ? ? C6aa C -0.0853(8) 0.6322(7) -0.4842(11) Uani 0.0640(16) 4 0.6 d ? ? ? N1aa N -0.0941(7) 0.5242(7) -0.5028(10) Uani 0.0640(16) 4 0.6 d ? ? ? C2aa C -0.0109(7) 0.4600(8) -0.3501(10) Uani 0.0640(16) 4 0.6 d ? ? ? C3aa C 0.0875(7) 0.4988(6) -0.1713(11) Uani 0.0640(16) 4 0.6 d ? ? ? C4aa C 0.0919(4) 0.6073(4) -0.1607(5) Uani 0.0640(16) 4 0.6 d ? ? ? H1a H 0.188291 0.726659 0.01968 Uiso 0.0768 4 0.6 d ? ? ? H2a H 0.238129 0.621355 0.120581 Uiso 0.0768 4 0.6 d ? ? ? H1c5aa H 0.018135 0.754821 -0.288552 Uiso 0.0768 4 0.6 d ? ? ? H1c6aa H -0.14542 0.675304 -0.594509 Uiso 0.0768 4 0.6 d ? ? ? H1c2aa H -0.021417 0.385092 -0.367974 Uiso 0.0768 4 0.6 d ? ? ? H1c3aa H 0.147671 0.454415 -0.063794 Uiso 0.0768 4 0.6 d ? ? ? H1n1aa H -0.154208 0.496296 -0.614633 Uiso 0.0768 4 0.6 d ? ? ? Nba N -0.1268(4) 0.6204(4) -0.5880(4) Uani 0.062(2) 4 0.4 d ? ? ? C5ba C 0.0321(10) 0.6931(6) -0.2608(11) Uani 0.062(2) 4 0.4 d ? ? ? C6ba C 0.1268(9) 0.6775(7) -0.0632(11) Uani 0.062(2) 4 0.4 d ? ? ? N1ba N 0.1653(7) 0.5763(7) 0.0011(10) Uani 0.062(2) 4 0.4 d ? ? ? C2ba C 0.1023(8) 0.4898(7) -0.1188(11) Uani 0.062(2) 4 0.4 d ? ? ? C3ba C 0.0027(8) 0.5065(6) -0.3155(11) Uani 0.062(2) 4 0.4 d ? ? ? C4ba C -0.0251(4) 0.6083(5) -0.3877(6) Uani 0.062(2) 4 0.4 d ? ? ? H1ba H -0.140533 0.680443 -0.650729 Uiso 0.0745 4 0.4 d ? ? ? H2ba H -0.176189 0.567897 -0.649548 Uiso 0.0745 4 0.4 d ? ? ? H1n1ba H 0.231314 0.566144 0.120866 Uiso 0.0745 4 0.4 d ? ? ? H1c5ba H 0.005402 0.763388 -0.311052 Uiso 0.0745 4 0.4 d ? ? ? H1c4ba H 0.16552 0.735979 0.028287 Uiso 0.0745 4 0.4 d ? ? ? H1c2ba H 0.127171 0.41963 -0.066396 Uiso 0.0745 4 0.4 d ? ? ? H1c3ba H -0.045686 0.448493 -0.399565 Uiso 0.0745 4 0.4 d ? ? ? loop_ _atom_site_aniso_label _atom_site_aniso_type_symbol _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Sb Sb 0.02837(16) 0.02888(18) 0.02555(16) -0.0003(2) 0.01376(12) 0.0001(2) Cl1a Cl 0.0442(7) 0.0430(9) 0.0463(8) 0.0121(7) 0.0214(6) 0.0183(7) Cl1b Cl 0.0446(7) 0.0436(9) 0.0434(8) -0.0125(7) 0.0203(6) -0.0108(7) Cl2a Cl 0.0287(10) 0.0424(12) 0.0391(14) 0.0020(6) 0.0166(10) -0.0004(7) Cl2b Cl 0.0414(13) 0.0505(14) 0.0484(16) 0.0013(7) 0.0265(12) 0.0028(8) Naa N 0.0558(18) 0.090(2) 0.0585(17) -0.0149(16) 0.0395(14) -0.0240(15) C5aa C 0.0558(18) 0.090(2) 0.0585(17) -0.0149(16) 0.0395(14) -0.0240(15) C6aa C 0.0558(18) 0.090(2) 0.0585(17) -0.0149(16) 0.0395(14) -0.0240(15) N1aa N 0.0558(18) 0.090(2) 0.0585(17) -0.0149(16) 0.0395(14) -0.0240(15) C2aa C 0.0558(18) 0.090(2) 0.0585(17) -0.0149(16) 0.0395(14) -0.0240(15) C3aa C 0.0558(18) 0.090(2) 0.0585(17) -0.0149(16) 0.0395(14) -0.0240(15) C4aa C 0.0558(18) 0.090(2) 0.0585(17) -0.0149(16) 0.0395(14) -0.0240(15) Nba N 0.070(2) 0.0538(19) 0.072(2) -0.0040(18) 0.045(2) -0.0024(19) C5ba C 0.070(2) 0.0538(19) 0.072(2) -0.0040(18) 0.045(2) -0.0024(19) C6ba C 0.070(2) 0.0538(19) 0.072(2) -0.0040(18) 0.045(2) -0.0024(19) N1ba N 0.070(2) 0.0538(19) 0.072(2) -0.0040(18) 0.045(2) -0.0024(19) C2ba C 0.070(2) 0.0538(19) 0.072(2) -0.0040(18) 0.045(2) -0.0024(19) C3ba C 0.070(2) 0.0538(19) 0.072(2) -0.0040(18) 0.045(2) -0.0024(19) C4ba C 0.070(2) 0.0538(19) 0.072(2) -0.0040(18) 0.045(2) -0.0024(19) loop_ _atom_site_Fourier_wave_vector_seq_id _jana_atom_site_Fourier_wave_vector_q1_coeff 1 1 loop_ _atom_site_occ_special_func_atom_site_label _atom_site_occ_special_func_crenel_c _atom_site_occ_special_func_crenel_w Naa 0.917 0.6 C5aa 0.9315 0.6 C6aa 0.8997 0.6 N1aa 0.8277 0.6 C2aa 0.7849 0.6 C3aa 0.8108 0.6 C4aa 0.8831 0.6 H1a 0.9627 0.6 H2a 0.8925 0.6 H1c5aa 0.9814 0.6 H1c6aa 0.9284 0.6 H1c2aa 0.735 0.6 H1c3aa 0.7812 0.6 H1n1aa 0.8091 0.6 Nba 0.3959 0.4 C5ba 0.4444 0.4 C6ba 0.434 0.4 N1ba 0.3666 0.4 C2ba 0.3089 0.4 C3ba 0.32 0.4 C4ba 0.3878 0.4 H1ba 0.436 0.4 H2ba 0.3609 0.4 H1n1ba 0.3598 0.4 H1c5ba 0.4913 0.4 H1c4ba 0.473 0.4 H1c2ba 0.2621 0.4 H1c3ba 0.2813 0.4 loop_ _atom_site_displace_Fourier_id _atom_site_displace_Fourier_atom_site_label _atom_site_displace_Fourier_axis _atom_site_displace_Fourier_wave_vector_seq_id Sbx1 Sb x 1 Sby1 Sb y 1 Sbz1 Sb z 1 Cl1ax1 Cl1a x 1 Cl1ay1 Cl1a y 1 Cl1az1 Cl1a z 1 Cl1bx1 Cl1b x 1 Cl1by1 Cl1b y 1 Cl1bz1 Cl1b z 1 Cl2ax1 Cl2a x 1 Cl2ay1 Cl2a y 1 Cl2az1 Cl2a z 1 Cl2bx1 Cl2b x 1 Cl2by1 Cl2b y 1 Cl2bz1 Cl2b z 1 loop_ _atom_site_displace_Fourier_param_id _atom_site_displace_Fourier_param_cos _atom_site_displace_Fourier_param_sin Sbx1 0.01930(3) -0.00445(3) Sby1 0.00005(4) 0.00173(4) Sbz1 0.02547(4) -0.00105(4) Cl1ax1 0.02961(18) 0.00228(13) Cl1ay1 0.01211(13) 0.00306(11) Cl1az1 0.0449(3) 0.0200(2) Cl1bx1 0.03038(19) 0.00158(13) Cl1by1 -0.01181(13) 0.00144(11) Cl1bz1 0.0423(3) 0.0155(2) Cl2ax1 0.01633(17) -0.00343(13) Cl2ay1 0.00468(11) 0.01230(14) Cl2az1 0.0142(3) 0.0008(2) Cl2bx1 0.0188(2) -0.00421(14) Cl2by1 -0.00700(13) -0.00898(14) Cl2bz1 0.0180(3) 0.0008(2) loop_ _jana_atom_site_displace_Legendre_atom_site_label _jana_atom_site_displace_Legendre_axis _jana_atom_site_displace_Legendre_param_order _jana_atom_site_displace_Legendre_param_coeff Naa x 1 0.009340(15) Naa y 1 0.002450(14) Naa z 1 0.02959(2) Naa x 2 0.01601(6) Naa y 2 0.03283(6) Naa z 2 -0.04430(10) C5aa x 1 0.01709(4) C5aa y 1 0.01016(3) C5aa z 1 0.01927(7) C5aa x 2 -0.0162(3) C5aa y 2 -0.0365(2) C5aa z 2 -0.0324(4) C6aa x 1 0.01908(10) C6aa y 1 0.02715(7) C6aa z 1 0.01221(14) C6aa x 2 -0.0026(3) C6aa y 2 -0.0700(2) C6aa z 2 0.0116(4) N1aa x 1 -0.0138(2) N1aa y 1 0.05737(13) N1aa z 1 -0.0345(3) N1aa x 2 0.0415(2) N1aa y 2 -0.05378(13) N1aa z 2 0.0632(3) C2aa x 1 -0.0587(3) C2aa y 1 0.04215(16) C2aa z 1 -0.0678(3) C2aa x 2 0.05603(16) C2aa y 2 -0.01860(9) C2aa z 2 0.0671(2) C3aa x 1 -0.0458(2) C3aa y 1 0.01005(15) C3aa z 1 -0.0267(3) C3aa x 2 0.05947(16) C3aa y 2 0.00105(12) C3aa z 2 0.0535(2) C4aa x 1 0.00340(5) C4aa y 1 0.00883(4) C4aa z 1 0.02099(7) C4aa x 2 0.02852(10) C4aa y 2 -0.00173(9) C4aa z 2 0.00185(15) H1a x 1 0.0101 H1a y 1 0.0118 H1a z 1 0.0102 H1a x 2 -0.0183 H1a y 2 0.0322 H1a z 2 -0.0902 H2a x 1 -0.0023 H2a y 1 -0.0092 H2a z 1 0.0336 H2a x 2 0.0399 H2a y 2 0.0533 H2a z 2 -0.026 H1c5aa x 1 0.0037 H1c5aa y 1 -0.0007 H1c5aa z 1 -0.0028 H1c5aa x 2 -0.0525 H1c5aa y 2 -0.0344 H1c5aa z 2 -0.0786 H1c6aa x 1 0.0224 H1c6aa y 1 0.0162 H1c6aa z 1 0.0132 H1c6aa x 2 -0.0328 H1c6aa y 2 -0.0973 H1c6aa z 2 -0.0059 H1c2aa x 1 -0.1052 H1c2aa y 1 0.0498 H1c2aa z 1 -0.1278 H1c2aa x 2 0.0435 H1c2aa y 2 -0.0057 H1c2aa z 2 0.0551 H1c3aa x 1 -0.08 H1c3aa y 1 -0.0103 H1c3aa z 1 -0.0479 H1c3aa x 2 0.063 H1c3aa y 2 0.0154 H1c3aa z 2 0.0577 H1n1aa x 1 -0.0216 H1n1aa y 1 0.0809 H1n1aa z 1 -0.0611 H1n1aa x 2 0.0439 H1n1aa y 2 -0.0627 H1n1aa z 2 0.0745 Nba x 1 0.00306(3) Nba y 1 -0.05298(4) Nba z 1 0.02394(7) Nba x 2 0.05119(4) Nba y 2 -0.05253(4) Nba z 2 0.04540(10) C5ba x 1 -0.00421(11) C5ba y 1 -0.00663(18) C5ba z 1 -0.0084(3) C5ba x 2 0.00740(17) C5ba y 2 0.0161(2) C5ba z 2 0.0162(4) C6ba x 1 -0.00559(14) C6ba y 1 0.02633(17) C6ba z 1 0.0040(4) C6ba x 2 -0.00006(19) C6ba y 2 0.04819(19) C6ba z 2 0.0334(5) N1ba x 1 -0.00028(13) N1ba y 1 0.00921(15) N1ba z 1 0.0286(4) N1ba x 2 0.03047(19) N1ba y 2 0.06983(16) N1ba z 2 0.1153(4) C2ba x 1 -0.02168(14) C2ba y 1 -0.01605(18) C2ba z 1 -0.0026(3) C2ba x 2 0.06478(18) C2ba y 2 0.03961(19) C2ba z 2 0.1848(4) C3ba x 1 -0.02081(10) C3ba y 1 -0.01689(17) C3ba z 1 0.0124(3) C3ba x 2 0.07118(16) C3ba y 2 -0.00646(18) C3ba z 2 0.1598(4) C4ba x 1 0.00134(4) C4ba y 1 -0.02707(8) C4ba z 1 0.02774(11) C4ba x 2 0.04339(8) C4ba y 2 -0.01298(9) C4ba z 2 0.06707(15) H1ba x 1 0.0061 H1ba y 1 -0.0759 H1ba z 1 -0.0053 H1ba x 2 0.036 H1ba y 2 -0.0455 H1ba z 2 0.0084 H2ba x 1 -0.0068 H2ba y 1 -0.0433 H2ba z 1 0.0339 H2ba x 2 0.0711 H2ba y 2 -0.0788 H2ba z 2 0.0808 H1n1ba x 1 -0.0002 H1n1ba y 1 0.0149 H1n1ba z 1 0.0258 H1n1ba x 2 0.0275 H1n1ba y 2 0.098 H1n1ba z 2 0.1331 H1c5ba x 1 -0.0199 H1c5ba y 1 -0.0127 H1c5ba z 1 -0.0627 H1c5ba x 2 -0.005 H1c5ba y 2 0.0123 H1c5ba z 2 -0.0036 H1c4ba x 1 -0.0237 H1c4ba y 1 0.0562 H1c4ba z 1 -0.0321 H1c4ba x 2 -0.0189 H1c4ba y 2 0.0504 H1c4ba z 2 0.0129 H1c2ba x 1 -0.05 H1c2ba y 1 -0.0302 H1c2ba z 1 -0.069 H1c2ba x 2 0.075 H1c2ba y 2 0.0453 H1c2ba z 2 0.2372 H1c3ba x 1 -0.0484 H1c3ba y 1 -0.0107 H1c3ba z 1 -0.0255 H1c3ba x 2 0.0867 H1c3ba y 2 -0.0305 H1c3ba z 2 0.2023 loop_ _atom_site_U_Fourier_id _atom_site_U_Fourier_atom_site_label _atom_site_U_Fourier_tens_elem _atom_site_U_Fourier_wave_vector_seq_id SbU111 Sb U11 1 SbU221 Sb U22 1 SbU331 Sb U33 1 SbU121 Sb U12 1 SbU131 Sb U13 1 SbU231 Sb U23 1 loop_ _atom_site_U_Fourier_param_id _atom_site_U_Fourier_param_cos _atom_site_U_Fourier_param_sin SbU111 0.0012(4) -0.0008(2) SbU221 0.0014(3) 0.0004(2) SbU331 -0.0007(4) -0.00151(19) SbU121 -0.00076(13) 0.00080(13) SbU131 0.0007(3) -0.00073(18) SbU231 0.00055(11) -0.00046(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_ssg_symmetry_1 _geom_bond_site_ssg_symmetry_2 _geom_bond_distance_av _geom_bond_distance_min _geom_bond_distance_max _geom_bond_publ_flag Sb Cl1a ? ? 2.382(5) 2.380(6) 2.382(6) ? Sb Cl1b ? ? 2.380(6) 2.374(6) 2.384(6) ? Sb Cl2a ? ? 2.665(8) 2.643(8) 2.697(8) ? Sb Cl2a ? 2_5655 3.191(6) 3.163(8) 3.206(8) ? Sb Cl2b ? ? 2.630(8) 2.595(9) 2.662(9) ? Sb Cl2b ? 2_5645 3.219(6) 3.180(8) 3.266(8) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_ssg_symmetry_1 _geom_angle_site_ssg_symmetry_2 _geom_angle_site_ssg_symmetry_3 _geom_angle_av _geom_angle_min _geom_angle_max _geom_angle_publ_flag Cl1a Sb Cl1b ? ? ? 92.8(3) 91.9(3) 93.3(3) ? Cl1a Sb Cl2a ? ? ? 88.2(2) 87.34(19) 89.2(2) ? Cl1a Sb Cl2a ? ? 2_5655 171.30(13) 169.17(12) 173.61(13) ? Cl1a Sb Cl2b ? ? ? 88.5(2) 88.24(19) 89.0(2) ? Cl1a Sb Cl2b ? ? 2_5645 81.1(3) 79.7(3) 83.4(3) ? Cl1b Sb Cl2a ? ? ? 88.1(2) 87.44(19) 88.8(2) ? Cl1b Sb Cl2a ? ? 2_5655 81.5(3) 80.4(3) 82.2(3) ? Cl1b Sb Cl2b ? ? ? 89.7(2) 88.45(19) 91.3(2) ? Cl1b Sb Cl2b ? ? 2_5645 170.02(13) 168.27(13) 170.97(14) ? Cl2a Sb Cl2a ? ? 2_5655 98.1(2) 95.2(2) 100.0(2) ? Cl2a Sb Cl2b ? ? ? 175.56(10) 175.38(9) 175.74(8) ? Cl2a Sb Cl2b ? ? 2_5645 83.8(2) 83.1(2) 85.2(2) ? Cl2a Sb Cl2b 2_5655 ? ? 84.9(2) 84.2(2) 86.3(2) ? Cl2a Sb Cl2b 2_5655 ? 2_5645 105.3(3) 105.2(3) 105.4(2) ? Cl2b Sb Cl2b ? ? 2_5645 98.0(2) 96.3(2) 100.8(2) ? data_IV _journal_date_recd_electronic 2017-10-18 _journal_date_accepted 2018-03-02 _journal_coeditor_code DK5062SUP1 _journal_paper_category FA _journal_techeditor_code B180366 _iucr_compatibility_tag ACTA95 _chemical_formula_sum 'C5 H7 Cl4 N2 Sb1' _chemical_formula_weight 358.69 _space_group_crystal_system monoclinic _space_group_ssg_name Cc(0\b0)0 loop_ _space_group_symop_ssg_id _space_group_symop_ssg_operation_algebraic 1 x1,x2,x3,x4 2 x1,-x2,x3+1/2,-x4 3 x1+1/2,x2+1/2,x3,x4 4 x1+1/2,-x2+1/2,x3+1/2,-x4 _cell_length_a 13.30(2) _cell_length_b 12.660(18) _cell_length_c 7.89(2) _cell_angle_alpha 90 _cell_angle_beta 123.8(2) _cell_angle_gamma 90 _cell_volume 1103(4) _cell_modulation_dimension 1 loop_ _cell_wave_vector_seq_id _cell_wave_vector_x _cell_wave_vector_y _cell_wave_vector_z 1 0.000000 0.668000 0.000000 _cell_formula_units_Z 4 _cell_measurement_temperature 244.97(13) _cell_measurement_reflns_used 6364 _cell_measurement_theta_min 3.2490 _cell_measurement_theta_max 29.1310 _exptl_crystal_type_of_structure mod _exptl_crystal_density_diffrn 2.192 _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.424 _exptl_crystal_description prism _exptl_crystal_size_max 0.233 _exptl_crystal_size_mid 0.162 _exptl_crystal_size_min 0.101 _exptl_absorpt_correction_T_min 0.84303 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _diffrn_ambient_temperature 244.97(13) _diffrn_ambient_environment N~2~ _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas' _diffrn_detector 'CCD plate' _diffrn_detector_type Atlas _diffrn_detector_area_resol_mean 10.6249 _diffrn_reflns_number 20894 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 29.43 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_max 0.91 _diffrn_measured_fraction_theta_full 0.98 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_unetI/netI 0.0449 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_index_m_1_min -1 _diffrn_reflns_limit_index_m_1_max 1 _diffrn_radiation_probe x-ray _reflns_number_total 7751 _reflns_number_gt 4489 _reflns_threshold_expression I>3\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_gt 0.0672 _refine_ls_R_factor_all 0.0521 _refine_ls_wR_factor_ref 0.0672 _refine_ls_goodness_of_fit_ref 1.90 _refine_ls_goodness_of_fit_gt 1.90 _refine_ls_number_reflns 4489 _refine_ls_number_parameters 135 _refine_ls_number_restraints 26 _refine_ls_number_constraints 3 _refine_ls_weighting_scheme sigma _refine_ls_weighting_details w=1/(\s^2^(I)+0.0016I^2^) _refine_ls_hydrogen_treatment constr _refine_ls_shift/su_max 0.0734 _refine_ls_shift/su_mean 0.0209 _refine_diff_density_max 1.32 _refine_diff_density_min -1.24 _refine_ls_extinction_method 'B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)' _refine_ls_extinction_coef -420(120) _refine_ls_abs_structure_details '2000 of Friedel pairs used in the refinement' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' Cl 0.1484 0.1585 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' Sb -0.5866 1.5461 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' #loop_ # _restr_distance_atom_site_label_1 # _restr_distance_site_symmetry_1 # _restr_distance_atom_site_label_2 # _restr_distance_site_symmetry_2 # _restr_distance_target # _restr_distance_target_weight_param # N1a ? C2a ? 1.4 0.01 # C2a ? C3a ? 1.4 0.01 # C3a ? C4a ? 1.4 0.01 # C4a ? C5a ? 1.4 0.01 # C5a ? C6a ? 1.4 0.01 # C6a ? N1a ? 1.4 0.01 # N1b ? C2b ? 1.4 0.01 # C2b ? C3b ? 1.4 0.01 # C3b ? C4b ? 1.4 0.01 # C4b ? C5b ? 1.4 0.01 # C5b ? C6b ? 1.4 0.01 # C6b ? N1b ? 1.4 0.01 # Nb ? C4b ? 1.45 0.01 # Na ? C4a ? 1.45 0.01 #loop_ # _restr_angle_atom_site_label_1 # _restr_angle_atom_site_label_2 # _restr_angle_atom_site_label_3 # _restr_angle_target # _restr_angle_target_weight_param # N1a C2a C3a 120 1 # C2a C3a C4a 120 1 # C3a C4a C5a 120 1 # C4a C5a C6a 120 1 # C5a C6a N1a 120 1 # C6a N1a C2a 120 1 # N1b C2b C3b 120 1 # C2b C3b C4b 120 1 # C3b C4b C5b 120 1 # C4b C5b C6b 120 1 # C5b C6b N1b 120 1 # C6b N1b C2b 120 1 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_adp_type _atom_site_U_iso_or_equiv _atom_site_site_symmetry_multiplicity _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.50070(4) 0.57246(2) 0.74945(8) Uani 0.0283(2) 4 1 d ? ? ? Cl1a Cl 0.3818(3) 0.70087(16) 0.5013(5) Uani 0.0471(16) 4 1 d ? ? ? Cl1b Cl 0.6215(2) 0.70322(14) 1.0037(4) Uani 0.0358(13) 4 1 d ? ? ? Cl2a Cl 0.6515(2) 0.57925(15) 0.6339(4) Uani 0.0346(14) 4 1 d ? ? ? Cl2b Cl 0.3442(3) 0.58118(17) 0.8601(6) Uani 0.0452(19) 4 1 d ? ? ? Naa N 0.1702(7) 0.6597(5) 0.0634(10) Uiso 0.034 4 0.6 d ? ? ? C5aa C -0.0132(9) 0.6767(4) -0.2755(13) Uiso 0.0478 4 0.6 d ? ? ? C6aa C -0.1072(8) 0.6315(6) -0.4532(11) Uiso 0.0421 4 0.6 d ? ? ? N1aa N -0.1166(7) 0.5225(5) -0.4665(11) Uiso 0.043 4 0.6 d ? ? ? C2aa C -0.0291(9) 0.4586(5) -0.3095(14) Uiso 0.0417 4 0.6 d ? ? ? C3aa C 0.0695(8) 0.5033(5) -0.1344(13) Uiso 0.0411 4 0.6 d ? ? ? C4aa C 0.0743(8) 0.6128(4) -0.1196(11) Uiso 0.0382 4 0.6 d ? ? ? H1naa H 0.23143 0.621482 0.153043 Uiso 0.0408 4 0.6 d ? ? ? H2naa H 0.167648 0.726583 0.085938 Uiso 0.0408 4 0.6 d ? ? ? H1c5aa H -0.00842 0.752055 -0.259655 Uiso 0.0574 4 0.6 d ? ? ? H1c6aa H -0.165065 0.674902 -0.565634 Uiso 0.0505 4 0.6 d ? ? ? H1c2aa H -0.03691 0.383151 -0.322237 Uiso 0.0501 4 0.6 d ? ? ? H1c3aa H 0.132006 0.460113 -0.027539 Uiso 0.0494 4 0.6 d ? ? ? H1n1aa H -0.178167 0.493454 -0.574669 Uiso 0.0516 4 0.6 d ? ? ? Nba N -0.1635(12) 0.6286(7) -0.5629(16) Uiso 0.0585 4 0.4 d ? ? ? C5ba C 0.0022(11) 0.6929(5) -0.2460(16) Uiso 0.0448 4 0.4 d ? ? ? C6ba C 0.1048(10) 0.6803(7) -0.0504(15) Uiso 0.044 4 0.4 d ? ? ? N1ba N 0.1446(9) 0.5788(9) 0.0240(14) Uiso 0.0386 4 0.4 d ? ? ? C2ba C 0.0848(13) 0.4896(7) -0.096(2) Uiso 0.0694 4 0.4 d ? ? ? C3ba C -0.0215(11) 0.5029(6) -0.2873(19) Uiso 0.0321 4 0.4 d ? ? ? C4ba C -0.0601(10) 0.6046(7) -0.3635(14) Uiso 0.0418 4 0.4 d ? ? ? H1nba H -0.186117 0.693899 -0.597613 Uiso 0.0702 4 0.4 d ? ? ? H2nba H -0.203645 0.577924 -0.649319 Uiso 0.0702 4 0.4 d ? ? ? H1c5ba H -0.025952 0.762489 -0.30024 Uiso 0.0537 4 0.4 d ? ? ? H1c6ba H 0.147703 0.740763 0.0321 Uiso 0.0528 4 0.4 d ? ? ? H1c2ba H 0.116893 0.420202 -0.0464 Uiso 0.0833 4 0.4 d ? ? ? H1c3ba H -0.067797 0.442653 -0.366019 Uiso 0.0385 4 0.4 d ? ? ? H1n1ba H 0.207823 0.570439 0.147542 Uiso 0.0463 4 0.4 d ? ? ? loop_ _atom_site_aniso_label _atom_site_aniso_type_symbol _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Sb1 Sb 0.0287(2) 0.0246(2) 0.0340(3) 0.0056(3) 0.0190(2) 0.0043(3) Cl1a Cl 0.0452(17) 0.0444(12) 0.061(2) 0.0134(12) 0.0351(17) 0.0179(12) Cl1b Cl 0.0268(13) 0.0292(9) 0.0302(15) -0.0047(9) 0.0027(13) -0.0056(9) Cl2a Cl 0.0229(14) 0.0408(12) 0.0363(19) -0.0005(9) 0.0141(14) -0.0104(10) Cl2b Cl 0.0382(18) 0.0376(13) 0.065(3) -0.0024(10) 0.0317(19) -0.0077(11) loop_ _atom_site_Fourier_wave_vector_seq_id _jana_atom_site_Fourier_wave_vector_q1_coeff 1 1 loop_ _atom_site_occ_special_func_atom_site_label _atom_site_occ_special_func_crenel_c _atom_site_occ_special_func_crenel_w Naa 0.9631 0.6 C5aa 0.9745 0.6 C6aa 0.9443 0.6 N1aa 0.8715 0.6 C2aa 0.8288 0.6 C3aa 0.8587 0.6 C4aa 0.9318 0.6 H1naa 0.9376 0.6 H2naa 1.0078 0.6 H1c5aa 1.0248 0.6 H1c6aa 0.9733 0.6 H1c2aa 0.7784 0.6 H1c3aa 0.8298 0.6 H1n1aa 0.8521 0.6 Nba 0.4239 0.4 C5ba 0.4668 0.4 C6ba 0.4584 0.4 N1ba 0.3906 0.4 C2ba 0.331 0.4 C3ba 0.3399 0.4 C4ba 0.4078 0.4 H1nba 0.4675 0.4 H2nba 0.39 0.4 H1c5ba 0.5133 0.4 H1c6ba 0.4988 0.4 H1c2ba 0.2847 0.4 H1c3ba 0.2997 0.4 H1n1ba 0.385 0.4 loop_ _atom_site_displace_Fourier_id _atom_site_displace_Fourier_atom_site_label _atom_site_displace_Fourier_axis _atom_site_displace_Fourier_wave_vector_seq_id Sb1x1 Sb1 x 1 Sb1y1 Sb1 y 1 Sb1z1 Sb1 z 1 Cl1ax1 Cl1a x 1 Cl1ay1 Cl1a y 1 Cl1az1 Cl1a z 1 Cl1bx1 Cl1b x 1 Cl1by1 Cl1b y 1 Cl1bz1 Cl1b z 1 Cl2ax1 Cl2a x 1 Cl2ay1 Cl2a y 1 Cl2az1 Cl2a z 1 Cl2bx1 Cl2b x 1 Cl2by1 Cl2b y 1 Cl2bz1 Cl2b z 1 loop_ _atom_site_displace_Fourier_param_id _atom_site_displace_Fourier_param_cos _atom_site_displace_Fourier_param_sin Sb1x1 0.02026(4) -0.00614(4) Sb1y1 -0.00080(5) 0.00249(5) Sb1z1 0.02500(7) -0.00326(7) Cl1ax1 0.0351(4) -0.0038(3) Cl1ay1 0.0103(2) -0.00082(18) Cl1az1 0.0435(6) 0.0098(5) Cl1bx1 0.0325(3) 0.0034(3) Cl1by1 -0.01537(17) 0.00303(15) Cl1bz1 0.0487(5) 0.0136(5) Cl2ax1 0.0214(3) 0.0003(3) Cl2ay1 0.00395(16) 0.0156(2) Cl2az1 0.0204(5) 0.0021(4) Cl2bx1 0.0159(3) -0.0092(3) Cl2by1 -0.00205(16) -0.00843(19) Cl2bz1 0.0147(6) -0.0039(5) loop_ _jana_atom_site_displace_Legendre_atom_site_label _jana_atom_site_displace_Legendre_axis _jana_atom_site_displace_Legendre_param_order _jana_atom_site_displace_Legendre_param_coeff Naa x 1 -0.0025(11) Naa y 1 0.0223(9) Naa z 1 -0.0052(17) Naa x 2 0.0006(16) Naa y 2 0.0302(14) Naa z 2 0.0000(16) C5aa x 1 -0.0052(8) C5aa y 1 0.0005(5) C5aa z 1 -0.0080(11) C5aa x 2 -0.0045(16) C5aa y 2 -0.0104(4) C5aa z 2 -0.0035(16) C6aa x 1 -0.0008(8) C6aa y 1 -0.0058(7) C6aa z 1 -0.0003(13) C6aa x 2 0.0027(16) C6aa y 2 -0.0324(11) C6aa z 2 0.0150(9) N1aa x 1 -0.0039(9) N1aa y 1 0.0093(8) N1aa z 1 -0.0121(14) N1aa x 2 0.0258(16) N1aa y 2 -0.0336(11) N1aa z 2 0.0609(12) C2aa x 1 -0.0160(10) C2aa y 1 0.0102(5) C2aa z 1 -0.0373(14) C2aa x 2 0.0379(16) C2aa y 2 -0.0100(4) C2aa z 2 0.080(2) C3aa x 1 -0.0075(7) C3aa y 1 0.0039(6) C3aa z 1 -0.0174(10) C3aa x 2 0.0315(16) C3aa y 2 0.0118(5) C3aa z 2 0.0653(13) C4aa x 1 0.0003(4) C4aa y 1 0.0092(6) C4aa z 1 0.0005(9) C4aa x 2 0.0087(16) C4aa y 2 0.0105(6) C4aa z 2 0.0201(7) H1naa x 1 0.0002(13) H1naa y 1 0.0213(10) H1naa z 1 0.000(2) H1naa x 2 0.0086(16) H1naa y 2 0.0459(19) H1naa z 2 0.0139(10) H2naa x 1 -0.0123(15) H2naa y 1 0.0310(11) H2naa z 1 -0.025(2) H2naa x 2 -0.0089(17) H2naa y 2 0.0243(13) H2naa z 2 -0.020(3) H1c5aa x 1 -0.0190(14) H1c5aa y 1 -0.0014(5) H1c5aa z 1 -0.034(2) H1c5aa x 2 -0.0131(16) H1c5aa y 2 -0.0089(4) H1c5aa z 2 -0.022(2) H1c6aa x 1 -0.0056(13) H1c6aa y 1 -0.0193(10) H1c6aa z 1 -0.0069(18) H1c6aa x 2 -0.0061(16) H1c6aa y 2 -0.0436(16) H1c6aa z 2 -0.0009(16) H1c2aa x 1 -0.0372(16) H1c2aa y 1 0.0139(5) H1c2aa z 1 -0.082(3) H1c2aa x 2 0.0439(16) H1c2aa y 2 -0.0077(5) H1c2aa z 2 0.090(3) H1c3aa x 1 -0.0166(12) H1c3aa y 1 -0.0035(8) H1c3aa z 1 -0.0352(16) H1c3aa x 2 0.0391(16) H1c3aa y 2 0.0262(10) H1c3aa z 2 0.078(2) H1n1aa x 1 -0.0080(13) H1n1aa y 1 0.0165(10) H1n1aa z 1 -0.0227(19) H1n1aa x 2 0.0308(16) H1n1aa y 2 -0.0467(16) H1n1aa z 2 0.0723(18) Nba x 1 -0.004(2) Nba y 1 -0.0680(18) Nba z 1 0.002(4) Nba x 2 0.025(2) Nba y 2 -0.050(3) Nba z 2 0.0244(13) C5ba x 1 -0.0314(13) C5ba y 1 0.0017(11) C5ba z 1 -0.037(2) C5ba x 2 0.009(2) C5ba y 2 -0.0079(5) C5ba z 2 0.018(3) C6ba x 1 -0.0312(17) C6ba y 1 0.0511(14) C6ba z 1 -0.022(3) C6ba x 2 0.004(2) C6ba y 2 0.0083(15) C6ba z 2 0.024(3) N1ba x 1 0.0003(19) N1ba y 1 0.0576(16) N1ba z 1 0.037(3) N1ba x 2 0.020(2) N1ba y 2 0.042(2) N1ba z 2 0.0738(6) C2ba x 1 0.0086(17) C2ba y 1 0.0246(13) C2ba z 1 0.042(3) C2ba x 2 0.058(2) C2ba y 2 0.0323(12) C2ba z 2 0.147(3) C3ba x 1 0.0092(12) C3ba y 1 0.0014(11) C3ba z 1 0.045(2) C3ba x 2 0.058(2) C3ba y 2 -0.0141(6) C3ba z 2 0.126(3) C4ba x 1 -0.0008(9) C4ba y 1 -0.0206(13) C4ba z 1 0.020(2) C4ba x 2 0.024(2) C4ba y 2 -0.0252(10) C4ba z 2 0.0431(5) H1nba x 1 -0.023(3) H1nba y 1 -0.088(2) H1nba z 1 -0.047(4) H1nba x 2 0.017(2) H1nba y 2 -0.032(3) H1nba z 2 0.008(3) H2nba x 1 0.008(3) H2nba y 1 -0.072(2) H2nba z 1 0.029(5) H2nba x 2 0.042(2) H2nba y 2 -0.078(3) H2nba z 2 0.0515(5) H1c5ba x 1 -0.056(2) H1c5ba y 1 -0.0149(9) H1c5ba z 1 -0.092(4) H1c5ba x 2 0.018(2) H1c5ba y 2 -0.0077(9) H1c5ba z 2 0.029(4) H1c6ba x 1 -0.058(2) H1c6ba y 1 0.0732(18) H1c6ba z 1 -0.065(4) H1c6ba x 2 0.008(2) H1c6ba y 2 -0.003(2) H1c6ba z 2 0.028(4) H1c2ba x 1 -0.004(2) H1c2ba y 1 0.0164(15) H1c2ba z 1 0.008(4) H1c2ba x 2 0.087(2) H1c2ba y 2 0.0518(15) H1c2ba z 2 0.215(4) H1c3ba x 1 -0.001(2) H1c3ba y 1 -0.0004(12) H1c3ba z 1 0.027(3) H1c3ba x 2 0.087(2) H1c3ba y 2 -0.0342(11) H1c3ba z 2 0.180(4) H1n1ba x 1 0.001(3) H1n1ba y 1 0.079(2) H1n1ba z 1 0.040(5) H1n1ba x 2 0.018(2) H1n1ba y 2 0.067(3) H1n1ba z 2 0.0842(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_ssg_symmetry_1 _geom_bond_site_ssg_symmetry_2 _geom_bond_distance_av _geom_bond_distance_min _geom_bond_distance_max _geom_bond_publ_flag Sb1 Cl1a ? ? 2.359(6) 2.352(7) 2.372(7) ? Sb1 Cl1b ? ? 2.406(6) 2.381(7) 2.426(7) ? Sb1 Cl2a ? ? 2.628(9) 2.564(9) 2.697(9) ? Sb1 Cl2a ? 2_5655 3.191(7) 3.128(8) 3.246(8) ? Sb1 Cl2b ? ? 2.673(10) 2.639(11) 2.708(11) ? Sb1 Cl2b ? 2_5645 3.239(7) 3.189(9) 3.304(9) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_ssg_symmetry_1 _geom_angle_site_ssg_symmetry_2 _geom_angle_site_ssg_symmetry_3 _geom_angle_av _geom_angle_min _geom_angle_max _geom_angle_publ_flag Cl1a Sb1 Cl1b ? ? ? 92.6(3) 91.6(3) 93.7(3) ? Cl1a Sb1 Cl2a ? ? ? 88.9(2) 87.0(2) 90.9(2) ? Cl1a Sb1 Cl2a ? ? 2_5655 170.06(19) 169.20(18) 170.8(2) ? Cl1a Sb1 Cl2b ? ? ? 87.6(2) 85.9(2) 89.2(2) ? Cl1a Sb1 Cl2b ? ? 2_5645 81.3(3) 79.9(3) 82.5(3) ? Cl1b Sb1 Cl2a ? ? ? 89.0(2) 86.5(2) 91.3(2) ? Cl1b Sb1 Cl2a ? ? 2_5655 81.2(3) 78.9(3) 83.4(2) ? Cl1b Sb1 Cl2b ? ? ? 88.9(2) 87.1(2) 90.5(2) ? Cl1b Sb1 Cl2b ? ? 2_5645 170.83(17) 167.47(18) 174.42(15) ? Cl2a Sb1 Cl2a ? ? 2_5655 98.67(19) 96.7(2) 100.45(18) ? Cl2a Sb1 Cl2b ? ? ? 175.48(11) 174.03(11) 176.95(10) ? Cl2a Sb1 Cl2b ? ? 2_5645 84.3(2) 82.41(19) 86.3(2) ? Cl2a Sb1 Cl2b 2_5655 ? ? 84.6(2) 82.8(2) 86.4(2) ? Cl2a Sb1 Cl2b 2_5655 ? 2_5645 105.7(2) 105.4(2) 106.0(2) ? Cl2b Sb1 Cl2b ? ? 2_5645 97.4(2) 93.9(2) 100.69(19) ? data_V _chemical_formula_sum 'C5 H7 Cl4 N2 Sb1' _chemical_formula_weight 358.69 _chemical_absolute_configuration ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yabc' _space_group_IT_number 14 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x+1/2,y+1/2,-z+1/2 3 -x,-y,-z 4 x+1/2,-y+1/2,z+1/2 _cell_length_a 13.2080(4) _cell_length_b 12.526(4) _cell_length_c 7.9251(3) _cell_angle_alpha 90 _cell_angle_beta 123.914(2) _cell_angle_gamma 90 _cell_volume 1088.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 199.9(2) _cell_measurement_reflns_used 8893 _cell_measurement_theta_min 3.2580 _cell_measurement_theta_max 29.1290 _exptl_crystal_type_of_structure cryst _exptl_crystal_density_diffrn 2.190 _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.466 _exptl_crystal_description prism _exptl_crystal_size_max 0.233 _exptl_crystal_size_mid 0.162 _exptl_crystal_size_min 0.101 _exptl_absorpt_correction_T_min 0.84110 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _diffrn_ambient_temperature 199.9(2) _diffrn_ambient_environment N~2~ _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas' _diffrn_detector 'CCD plate' _diffrn_detector_type Atlas _diffrn_detector_area_resol_mean 10.6249 _diffrn_reflns_number 14021 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 29.45 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_max 0.91 _diffrn_measured_fraction_theta_full 0.98 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_unetI/netI 0.0121 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_radiation_probe x-ray _reflns_number_total 2744 _reflns_number_gt 2519 _reflns_threshold_expression I>3\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0139 _refine_ls_wR_factor_gt 0.0268 _refine_ls_R_factor_all 0.0187 _refine_ls_wR_factor_ref 0.0304 _refine_ls_goodness_of_fit_ref 1.20 _refine_ls_goodness_of_fit_gt 1.10 _refine_ls_number_reflns 2744 _refine_ls_number_parameters 109 _refine_ls_weighting_scheme sigma _refine_ls_weighting_details w=1/(\s^2^(I)+0.0016I^2^) _refine_ls_hydrogen_treatment constr _refine_ls_shift/su_max 0.0196 _refine_ls_shift/su_mean 0.0017 _refine_diff_density_max 0.70 _refine_diff_density_min -0.73 _refine_ls_extinction_method none loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' Cl 0.1484 0.1585 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' Sb -0.5866 1.5461 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' _audit_creation_method 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_adp_type _atom_site_U_iso_or_equiv _atom_site_site_symmetry_multiplicity _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_disorder_assembly _atom_site_disorder_group Sb Sb 0.511351(12) 0.571387(9) 0.759189(15) Uani 0.01917(8) 4 1 d ? ? ? Cl1a Cl 0.40620(4) 0.71383(4) 0.52663(6) Uani 0.0283(2) 4 1 d ? ? ? Cl1b Cl 0.64651(4) 0.69029(4) 1.02697(6) Uani 0.0290(2) 4 1 d ? ? ? Cl2a Cl 0.66408(5) 0.57125(3) 0.63829(9) Uani 0.0294(2) 4 1 d ? ? ? Cl2b Cl 0.35467(5) 0.58915(4) 0.86125(7) Uani 0.0264(2) 4 1 d ? ? ? N N 0.16653(15) 0.65019(12) 0.0625(2) Uani 0.0348(8) 4 1 d ? ? ? C5 C -0.00912(17) 0.68284(18) -0.2746(2) Uani 0.0283(9) 4 1 d ? ? ? C6 C -0.1047(2) 0.64168(19) -0.4507(3) Uani 0.0364(9) 4 1 d ? ? ? N1 N -0.12220(17) 0.53468(16) -0.4766(3) Uani 0.0386(8) 4 1 d ? ? ? C2 C -0.0455(2) 0.46623(18) -0.3300(4) Uani 0.0385(12) 4 1 d ? ? ? C3 C 0.0533(2) 0.50224(16) -0.1492(3) Uani 0.0319(10) 4 1 d ? ? ? C4 C 0.07266(16) 0.61308(13) -0.1166(2) Uani 0.0247(8) 4 1 d ? ? ? H1n H 0.176746 0.718631 0.084184 Uiso 0.0417 4 1 d ? ? ? H2n H 0.217141 0.605788 0.156704 Uiso 0.0417 4 1 d ? ? ? H5 H 0.002704 0.758687 -0.257763 Uiso 0.0339 4 1 d ? ? ? H6 H -0.16061 0.688935 -0.558501 Uiso 0.0437 4 1 d ? ? ? H2 H -0.060125 0.390862 -0.352103 Uiso 0.0462 4 1 d ? ? ? H3 H 0.108761 0.452678 -0.046122 Uiso 0.0382 4 1 d ? ? ? H1 H -0.184369 0.509994 -0.590372 Uiso 0.0463 4 1 d ? ? ? loop_ _atom_site_aniso_label _atom_site_aniso_type_symbol _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Sb Sb 0.01957(9) 0.01811(10) 0.01690(9) -0.00087(4) 0.00838(7) 0.00009(3) Cl1a Cl 0.0276(2) 0.0253(2) 0.0255(2) 0.00385(18) 0.0108(2) 0.00684(16) Cl1b Cl 0.0267(2) 0.0262(2) 0.0238(2) -0.00599(18) 0.00778(19) -0.00451(16) Cl2a Cl 0.0254(3) 0.0293(3) 0.0326(3) 0.00092(16) 0.0157(2) -0.00077(16) Cl2b Cl 0.0239(2) 0.0260(2) 0.0268(2) -0.00205(17) 0.0126(2) -0.00051(17) N N 0.0298(9) 0.0358(9) 0.0259(8) -0.0016(8) 0.0076(7) -0.0069(7) C5 C 0.0332(10) 0.0259(11) 0.0252(9) 0.0024(7) 0.0159(8) 0.0033(7) C6 C 0.0295(11) 0.0507(13) 0.0246(10) 0.0048(10) 0.0125(9) 0.0031(9) N1 N 0.0274(9) 0.0595(12) 0.0287(9) -0.0159(9) 0.0156(8) -0.0190(8) C2 C 0.0502(14) 0.0338(12) 0.0453(13) -0.0157(11) 0.0351(12) -0.0171(10) C3 C 0.0393(12) 0.0267(10) 0.0329(11) 0.0003(8) 0.0222(10) -0.0018(8) C4 C 0.0255(9) 0.0268(9) 0.0244(9) 0.0012(8) 0.0155(8) -0.0009(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Sb Cl1a ? ? 2.3775(10) ? Sb Cl1b ? ? 2.3835(7) ? Sb Cl2a ? ? 2.6728(9) ? Sb Cl2a ? 3_666 3.2155(8) ? Sb Cl2b ? ? 2.6181(7) ? Sb Cl2b ? 3_667 3.2068(10) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1a Sb Cl1b ? ? ? 92.56(3) ? Cl1a Sb Cl2a ? ? ? 87.35(2) ? Cl1a Sb Cl2a ? ? 3_666 82.39(2) ? Cl1a Sb Cl2b ? ? ? 87.43(2) ? Cl1a Sb Cl2b ? ? 3_667 167.34(2) ? Cl1b Sb Cl2a ? ? ? 88.82(2) ? Cl1b Sb Cl2a ? ? 3_666 172.66(2) ? Cl1b Sb Cl2b ? ? ? 90.02(2) ? Cl1b Sb Cl2b ? ? 3_667 79.02(3) ? Cl2a Sb Cl2a ? ? 3_666 85.64(2) ? Cl2a Sb Cl2b ? ? ? 174.602(16) ? Cl2a Sb Cl2b ? ? 3_667 101.77(2) ? Cl2a Sb Cl2b 3_666 ? ? 95.06(2) ? Cl2a Sb Cl2b 3_666 ? 3_667 106.82(2) ? Cl2b Sb Cl2b ? ? 3_667 83.17(2) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N H1n Cl2a ? ? 4_464 0.87 2.69 3.544(3) 168.60 ? N H2n Cl2a ? ? 3_666 0.87 2.68 3.522(2) 163.63 ? N1 H1 Cl2b ? ? 3_565 0.87 2.41 3.2684(17) 167.80 ?