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Growth-induced incommensurability observed in the organic co-crystal hexamethylenetetramine resorcinol

Authors:

Rodriguez, Soraya Maria Belluga; Palatinus, Lukas; Petricek, Vaclav; Chapuis, Gervais

Journal:

Acta Crystallographica, Section B 62 1043-1050 (2006)

DOI:

https://doi.org/10.1107/S0108768106030382

B-IncStrDB ID: 5BJwqu0N6AI Entry date: 2022-01-27 Last revision: 2022-01-27

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Chemical data

Common Name: hexamethylenetetramine resorcinol [ Help ]

Structural Formula Sum: C12 H18 N4 O2 [ Help ]

Structural Formula: C6 H12 N4 . C6 H6 O2 [ Help ]

Formula weight: 250.3 Da [ Help ]

Crystallographic data and experimental details

Crystal system: orthorhombic [ Help ]

Superspace group name: Xmcm(0β0)s0s [ Help ]

Symmetry operations of the superspace group: [ Help ]

Operation code Operation in algebraic form
1 x1,x2,x3,x4
2 -x1,x2,x3,1/2+x4
3 x1,x2,1/2-x3,1/2+x4
4 -x1,x2,1/2-x3,x4
5 -x1,-x2,-x3,-x4
6 x1,-x2,-x3,1/2-x4
7 -x1,-x2,1/2+x3,1/2-x4
8 x1,-x2,1/2+x3,-x4
9 1/2+x1,1/2+x2,x3,1/2+x4
10 1/2-x1,1/2+x2,x3,x4
11 1/2+x1,1/2+x2,1/2-x3,x4
12 1/2-x1,1/2+x2,1/2-x3,1/2+x4
13 1/2-x1,1/2-x2,-x3,1/2-x4
14 1/2+x1,1/2-x2,-x3,-x4
15 1/2-x1,1/2-x2,1/2+x3,-x4
16 1/2+x1,1/2-x2,1/2+x3,1/2-x4

a: 10.3474(14) Å [ Help ]

b: 7.0763(6) Å [ Help ]

c: 16.8321(17) Å [ Help ]

α: 90 ° [ Help ]

β: 90 ° [ Help ]

γ: 90 ° [ Help ]

Volume: 1232.5 Å3 [ Help ]

Z: 4 [ Help ]

Modulation dimension: 1 [ Help ]

Measured independent wave vectors: [ Help ]

Wave vector id q_x q_y q_z
1 0.00000 0.376(5) 0.00000

μ: 0.091 mm-1 [ Help ]

Absorption correction type: none [ Help ]

Minimum transmission factor: 1.000 [ Help ]

Maximum transmission factor: 1.000 [ Help ]

Refinement details

Total nb. of reflections: 2462 [ Help ]

Nb. of observed reflections: 1098 [ Help ]

Intense reflections threshold: I>3σ(I) [ Help ]

Refinement based on: F [ Help ]

R(all): 0.0932 [ Help ]

R(obs): 0.0435 [ Help ]

wR(obs): 0.0605 [ Help ]

wR(all): 0.0716 [ Help ]

S(all): 1.66 [ Help ]

Nb. of reflections: 2462 [ Help ]

Nb. of parameters: 86 [ Help ]

Refinement of hydrogen atoms: constr [ Help ]

Weighting scheme: sigma [ Help ]

Weighting scheme remarks: w=1/(σ2(F)+0.0004F2) [ Help ]

Δ/σ(max): 0.0004 [ Help ]

Δ/σ(mean): 0.0000 [ Help ]

Δρ(max): 0.20 e_Å-3 [ Help ]

Δρ(min): -0.13 e_Å-3 [ Help ]

Extinction method: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974) [ Help ]

Extinction coefficient: 4.2(3) [ Help ]

Structural Information

Average Structure: [ Help ]

Atom symbol Atom site label x y z Uiso/equiv ADP type Coords from (d)iffraction or (c)alculated Coords restraints or constraints Occupancy Disordered cluster Disordered group
C C3a 0.1047(2) 0 0 0.0547(6) Uani d . 0.5 . .
C C4a -0.1596(4) 0 0 0.0625(7) Uani d . 0.5 . .
C C1a 0.0380(3) 0.1419(2) 0.03809(10) 0.0493(4) Uani d . 0.5 . .
C C2a -0.0946(3) 0.1434(2) 0.03839(10) 0.0561(5) Uani d . 0.5 . .
O O1a 0.1089(3) 0.2782(2) 0.07462(10) 0.0822(4) Uani d . 0.5 . .
H H13a 0.2003(10) 0 0 0.0656 Uiso d . 0.5 . .
H H14a -0.2551(11) 0 0 0.075 Uiso d . 0.5 . .
H H12a -0.1427(2) 0.246872 0.065995 0.0673 Uiso d . 0.5 . .
H H10a 0.0536(7) 0.3644(18) 0.1058(10) 0.0987 Uiso d . 0.5 . .
N N2a 0.5 0.03454(11) 0.32215(5) 0.0522(3) Uani d . 1 . .
N N1a 0.38296(11) 0.2764(2) 0.25 0.0719(4) Uani d . 1 . .
C C6a 0.5 -0.0808(2) 0.25 0.0542(4) Uani d . 1 . .
C C5a 0.5 0.3908(3) 0.25 0.0840(7) Uani d . 1 . .
C C7a 0.38507(8) 0.15547(19) 0.32013(5) 0.0680(3) Uani d . 1 . .
H H16a 0.5767(11) -0.1607(17) 0.25 0.065 Uiso d . 1 . .
H H15a 0.5 0.470(2) 0.3011(7) 0.1008 Uiso d . 1 . .
H H17a 0.305686 0.07491(11) 0.320931 0.0816 Uiso d . 1 . .
H H27a 0.382512 0.23558(11) 0.369042 0.0816 Uiso d . 1 . .

ADP components: [ Help ]

Atom site label U11 U22 U33 U12 U13 U23 Atom site symbol
C3a 0.0430(10) 0.0659(12) 0.0553(10) 0 0 -0.0144(9) C
C4a 0.0448(11) 0.0617(12) 0.0810(15) 0 0 0.0025(10) C
C1a 0.0514(9) 0.0517(7) 0.0447(6) -0.0014(6) 0.0030(5) -0.0087(5) C
C2a 0.0533(8) 0.0547(8) 0.0602(8) 0.0088(7) 0.0098(7) 0.0018(6) C
O1a 0.0650(7) 0.0811(7) 0.1007(9) -0.0049(5) 0.0044(5) -0.0519(7) O
N2a 0.0670(5) 0.0440(4) 0.0457(4) 0 0 0.0076(3) N
N1a 0.0952(8) 0.0573(5) 0.0630(6) 0.0319(5) 0 0 N
C6a 0.0656(8) 0.0343(6) 0.0627(8) 0 0 0 C
C5a 0.1574(19) 0.0343(6) 0.0602(9) 0 0 0 C
C7a 0.0779(6) 0.0689(5) 0.0572(5) 0.0151(4) 0.0168(3) -0.0008(3) C

Fourier Wave Vectors (explicit: q_x,q_y,q_z or coefficients: q_1,q_2,...): [ Help ]

Wave vector code q_x q_y q_z
1 0.00000 0.37600 0.00000

Definition of the occupation Fourier series: [ Help ]

Modulation code Atom site label Wave vector code
C3ao1 C3a 1
C4ao1 C4a 1
C1ao1 C1a 1
C2ao1 C2a 1
O1ao1 O1a 1
H13ao1 H13a 1
H14ao1 H14a 1
H12ao1 H12a 1
H10ao1 H10a 1

Occupation Fourier coefficients: [ Help ]

Modulation code Cosine coefficient Sine coefficient
C3ao1 0 0.2804
C4ao1 0 0.2804
C1ao1 0 0.2804
C2ao1 0 0.2804
O1ao1 0 0.2804
H13ao1 0 0.2804
H14ao1 0 0.2804
H12ao1 0 0.2804
H10ao1 0 0.2804

Definition of the displacive (translational) Fourier series: [ Help ]

Modulation code Atom site label Displacement axis Wave vector code
C3ax1 C3a x 1
C3ay1 C3a y 1
C3az1 C3a z 1
C4ax1 C4a x 1
C4ay1 C4a y 1
C4az1 C4a z 1
C1ax1 C1a x 1
C1ay1 C1a y 1
C1az1 C1a z 1
C2ax1 C2a x 1
C2ay1 C2a y 1
C2az1 C2a z 1
O1ax1 O1a x 1
O1ay1 O1a y 1
O1az1 O1a z 1
H13ax1 H13a x 1
H13ay1 H13a y 1
H13az1 H13a z 1
H14ax1 H14a x 1
H14ay1 H14a y 1
H14az1 H14a z 1
H12ax1 H12a x 1
H12ay1 H12a y 1
H12az1 H12a z 1
H11ax1 H10a x 1
H11ay1 H10a y 1
H11az1 H10a z 1
N2ax1 N2a x 1
N2ay1 N2a y 1
N2az1 N2a z 1
N1ax1 N1a x 1
N1ay1 N1a y 1
N1az1 N1a z 1
C6ax1 C6a x 1
C6ay1 C6a y 1
C6az1 C6a z 1
C5ax1 C5a x 1
C5ay1 C5a y 1
C5az1 C5a z 1
C7ax1 C7a x 1
C7ay1 C7a y 1
C7az1 C7a z 1
H16ax1 H16a x 1
H16ay1 H16a y 1
H16az1 H16a z 1
H15ax1 H15a x 1
H15ay1 H15a y 1
H15az1 H15a z 1
H17ax1 H17a x 1
H17ay1 H17a y 1
H17az1 H17a z 1
H27ax1 H27a x 1
H27ay1 H27a y 1
H27az1 H27a z 1

Displacive (translational) Fourier coefficients: [ Help ]

Modulation code Cosine coefficient Sine coefficient
C3ax1 0 -0.00010(15)
C3ay1 0.0090(2) 0
C3az1 -0.00386(11) 0
C4ax1 0 -0.00010(15)
C4ay1 0.0026(2) 0
C4az1 0.00692(11) 0
C1ax1 0.00251(8) -0.00010(15)
C1ay1 0.00739(18) 0.00049(10)
C1az1 -0.00114(9) -0.00032(7)
C2ax1 0.00252(8) -0.00010(15)
C2ay1 0.00419(18) 0.00050(10)
C2az1 0.00427(9) -0.00033(7)
O1ax1 0.00491(16) -0.00010(15)
O1ay1 0.0091(2) 0.0010(2)
O1az1 -0.00403(11) -0.00064(13)
H13ax1 0 -0.00010(15)
H13ay1 0.0113(3) 0
H13az1 -0.00776(14) 0
H14ax1 0 -0.00010(15)
H14ay1 0.0003(3) 0
H14az1 0.01081(14) 0
H12ax1 0.00434(14) -0.00010(15)
H12ay1 0.0030(2) 0.00085(18)
H12az1 0.00623(10) -0.00056(12)
H11ax1 0.0073(2) -0.00010(15)
H11ay1 0.00777(19) 0.0014(3)
H11az1 -0.00178(10) -0.00083(17)
N2ax1 -0.00575(7) 0.00378(7)
N2ay1 0 0
N2az1 0 0
N1ax1 0 0
N1ay1 0 0
N1az1 -0.00353(4) 0.00232(4)
C6ax1 0 0
C6ay1 0 0
C6az1 0 0
C5ax1 0 0
C5ay1 0 0
C5az1 0 0
C7ax1 -0.00559(7) 0.00368(6)
C7ay1 0 0
C7az1 -0.00346(4) 0.00228(4)
H16ax1 0 0
H16ay1 0 0
H16az1 0.00231(4) -0.00152(3)
H15ax1 -0.00407(7) 0.00268(6)
H15ay1 0 0
H15az1 0 0
H17ax1 -0.00566(7) 0.00372(7)
H17ay1 0 0
H17az1 -0.00586(7) 0.00385(7)
H27ax1 -0.00949(11) 0.00624(11)
H27ay1 0 0
H27az1 -0.00354(4) 0.00233(4)