Hydrogen-bond patterns and the structures of 1,4-cyclohexanediol: 2:1 cis:trans-1,4-cyclohexanediol

Loehlin, J.H.; Lee, M.; Woo, C.M.

doi:10.1107/S0108768108019460

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Hydrogen-bond patterns and the structures of 1,4-cyclohexanediol: 2:1 cis:trans-1,4-cyclohexanediol

J. H. Loehlin, M. Lee and C. M. Woo

The structure of a co-crystal with both trans and cis isomers of 1,4-cyclohexanediol (1,4-CHD) is reported. The intermolecular hydrogen-bond patterns are described and compared with those of the all trans structure, using the graph-set model. A second crystal with possible cis/trans disorder is also described. The results of molecular modeling of the simple isomers and conformers are compared with the known structures.

Keywords: hydrogen bonding; graph-set model; molecular geometry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108019460/bk5075sup1.cif Contains datablocks CHDct, CHDdis
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019460/bk5075CHDctsup2.hkl Contains datablock CHDct
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019460/bk5075CHDdissup3.hkl Contains datablock CHDdis

CCDC references: 705586; 705587

Computing details top

Data collection: omega scans 0.3deg/frame, 1271 frames for CHDct; XSCANS (Siemens, 1993) for CHDdis. Cell refinement: SMART for CHDct; XSCANS for CHDdis. Data reduction: SAINT for CHDct; XSCANS for CHDdis. Program(s) used to solve structure: SIR97 for CHDct; SIR97 (Altomare et al. 1994) for CHDdis. Program(s) used to refine structure: CRYSTALS (Watkin et al. 2001) for CHDct. Molecular graphics: CAMERON (Watkin et al. 1996) Mercury (Bruno, et al. 2002) for CHDct. Software used to prepare material for publication: CRYSTALS (Watkin et al. 2001) for CHDct.

Figures top

(CHDct) cis-1,4-cyclohexane-1,4-diol-trans-1,4-cyclohexane-1,4-diol (2/1) top

Crystal data top

2(C₆H₁₂O₂)·C₆H₁₂O₂	F(000) = 384.000
M_r = 348.47	D_x = 1.169 Mg m⁻³
Monoclinic, P2₁/c	Melting point: not measured K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.453 (2) Å	Cell parameters from 1407 reflections
b = 11.678 (4) Å	θ = 2.3–27.9°
c = 13.396 (4) Å	µ = 0.09 mm⁻¹
β = 101.378 (6)°	T = 193 K
V = 989.7 (6) Å³	Narrow plate, colorless
Z = 2	0.20 × 0.14 × 0.12 mm

Data collection top

Bruker SMART CCD diffractometer	R_int = 0.07
Graphite monochromator	θ_max = 27.9°, θ_min = 2.3°
ω/2θ scans	h = −8→7
6517 measured reflections	k = −15→14
2331 independent reflections	l = −17→11
1407 reflections with I > 3.00u(I)

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]2 24.1 37.9 18.5 4.67
S = 1.02	(Δ/σ)_max = 0.000225
1407 reflections	Δρ_max = 0.24 e Å⁻³
122 parameters	Δρ_min = −0.22 e Å⁻³

Crystal data top

2(C₆H₁₂O₂)·C₆H₁₂O₂	V = 989.7 (6) Å³
M_r = 348.47	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.453 (2) Å	µ = 0.09 mm⁻¹
b = 11.678 (4) Å	T = 193 K
c = 13.396 (4) Å	0.20 × 0.14 × 0.12 mm
β = 101.378 (6)°

Data collection top

Bruker SMART CCD diffractometer	1407 reflections with I > 3.00u(I)
6517 measured reflections	R_int = 0.07
2331 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	122 parameters
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.24 e Å⁻³
1407 reflections	Δρ_min = −0.22 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2962 (3)	0.45216 (17)	0.12641 (16)	0.0444
C2	0.1156 (3)	0.50412 (16)	0.16674 (16)	0.0417
C3	0.0901 (3)	0.63049 (18)	0.14109 (19)	0.0557
C4	0.2932 (3)	0.69751 (17)	0.17767 (16)	0.0467
C5	0.4743 (4)	0.6444 (2)	0.1387 (2)	0.0641
C6	0.4989 (3)	0.5168 (2)	0.1662 (2)	0.0616
O7	0.3246 (3)	0.33547 (13)	0.15463 (15)	0.0688
O8	0.3322 (2)	0.70146 (12)	0.28547 (11)	0.0467
O9	−0.0356 (3)	0.21040 (11)	0.09600 (13)	0.0503
C10	0.0033 (3)	0.09267 (15)	0.07315 (15)	0.0388
C11	−0.2015 (3)	0.03172 (15)	0.02757 (15)	0.0394
C12	−0.1580 (3)	−0.09117 (15)	−0.00105 (15)	0.0411
H11	0.2606 (3)	0.45758 (17)	0.05045 (16)	0.0527
H21	0.1426 (3)	0.49452 (16)	0.24238 (16)	0.0493
H22	−0.0177 (3)	0.46332 (16)	0.13554 (16)	0.0493
H31	−0.0227 (3)	0.66253 (18)	0.17456 (19)	0.0631
H32	0.0471 (3)	0.63942 (18)	0.06559 (19)	0.0631
H41	0.2781 (3)	0.77734 (17)	0.15019 (16)	0.0538
H51	0.6078 (4)	0.6851 (2)	0.1698 (2)	0.0795
H52	0.4483 (4)	0.6530 (2)	0.0629 (2)	0.0795
H61	0.5371 (3)	0.5084 (2)	0.2419 (2)	0.0747
H62	0.6140 (3)	0.4838 (2)	0.1349 (2)	0.0747
H71	0.200 (5)	0.296 (2)	0.137 (2)	0.072 (8)
H81	0.445 (5)	0.743 (3)	0.306 (2)	0.084 (9)
H91	−0.125 (4)	0.2054 (18)	0.1408 (18)	0.053 (6)
H101	0.0658 (3)	0.05106 (15)	0.13927 (15)	0.0472
H111	−0.2956 (3)	0.03076 (15)	0.07858 (15)	0.0486
H112	−0.2732 (3)	0.07362 (15)	−0.03484 (15)	0.0486
H121	−0.2937 (3)	−0.12759 (15)	−0.03534 (15)	0.0500
H122	−0.0971 (3)	−0.13502 (15)	0.06203 (15)	0.0500

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0340 (10)	0.0455 (11)	0.0534 (11)	0.0001 (8)	0.0078 (8)	−0.0099 (9)
C2	0.0295 (9)	0.0400 (10)	0.0549 (12)	−0.0009 (7)	0.0062 (8)	−0.0047 (8)
C3	0.0381 (11)	0.0448 (11)	0.0759 (15)	0.0049 (8)	−0.0090 (10)	−0.0010 (10)
C4	0.0478 (12)	0.0352 (9)	0.0536 (12)	−0.0053 (8)	0.0018 (9)	0.0107 (8)
C5	0.0617 (15)	0.0686 (15)	0.0705 (14)	−0.0247 (12)	0.0336 (12)	−0.0123 (13)
C6	0.0275 (9)	0.0639 (15)	0.0944 (18)	−0.0022 (9)	0.0140 (10)	−0.0253 (12)
O7	0.0431 (9)	0.0391 (8)	0.1119 (15)	0.0090 (7)	−0.0148 (9)	−0.0152 (8)
O8	0.0454 (8)	0.0436 (7)	0.0530 (9)	−0.0132 (6)	0.0144 (6)	−0.0038 (6)
O9	0.0560 (8)	0.0339 (7)	0.0676 (9)	−0.0045 (6)	0.0284 (8)	−0.0093 (6)
C10	0.0390 (10)	0.0304 (9)	0.0490 (10)	−0.0003 (7)	0.0124 (8)	−0.0020 (7)
C11	0.0380 (10)	0.0349 (8)	0.0480 (11)	−0.0013 (7)	0.0149 (8)	0.0013 (8)
C12	0.0393 (9)	0.0354 (9)	0.0513 (11)	−0.0044 (7)	0.0154 (8)	−0.0017 (8)

Geometric parameters (Å, º) top

C1—C2	1.505 (2)	C5—H52	1.000
C1—C6	1.513 (3)	C6—H61	1.000
C1—O7	1.416 (3)	C6—H62	1.000
C1—H11	1.000	O7—H71	0.92 (3)
C2—C3	1.517 (3)	O8—H81	0.87 (3)
C2—H21	1.000	O9—C10	1.441 (2)
C2—H22	1.000	O9—H91	0.91 (2)
C3—C4	1.522 (3)	C10—C11	1.519 (3)
C3—H31	1.000	C10—C12ⁱ	1.520 (2)
C3—H32	1.000	C10—H101	1.021
C4—C5	1.505 (3)	C11—C12	1.526 (2)
C4—O8	1.417 (3)	C11—H111	1.000
C4—H41	1.000	C11—H112	1.000
C5—C6	1.536 (3)	C12—H121	1.000
C5—H51	1.000	C12—H122	1.000

C2—C1—C6	110.42 (17)	H51—C5—H52	109.465
C2—C1—O7	111.14 (16)	C1—C6—C5	110.97 (19)
C6—C1—O7	109.16 (18)	C1—C6—H61	109.37 (14)
C2—C1—H11	107.53 (11)	C5—C6—H61	109.39 (14)
C6—C1—H11	109.65 (14)	C1—C6—H62	108.77 (11)
O7—C1—H11	108.91 (11)	C5—C6—H62	108.85 (12)
C1—C2—C3	111.58 (17)	H61—C6—H62	109.464
C1—C2—H21	109.05 (11)	C1—O7—H71	110.9 (17)
C3—C2—H21	109.15 (12)	C4—O8—H81	107.7 (19)
C1—C2—H22	108.70 (10)	C10—O9—H91	103.7 (13)
C3—C2—H22	108.85 (11)	O9—C10—C11	111.00 (14)
H21—C2—H22	109.468	O9—C10—C12ⁱ	108.04 (15)
C2—C3—C4	112.29 (16)	C11—C10—C12ⁱ	111.57 (16)
C2—C3—H31	108.57 (12)	O9—C10—H101	108.99 (11)
C4—C3—H31	108.66 (13)	C11—C10—H101	106.80 (10)
C2—C3—H32	109.06 (12)	C12ⁱ—C10—H101	110.40 (10)
C4—C3—H32	108.75 (12)	C10—C11—C12	110.71 (14)
H31—C3—H32	109.462	C10—C11—H111	109.20 (10)
C3—C4—C5	110.75 (19)	C12—C11—H111	109.13 (9)
C3—C4—O8	108.26 (18)	C10—C11—H112	109.20 (10)
C5—C4—O8	111.92 (19)	C12—C11—H112	109.14 (11)
C3—C4—H41	110.19 (11)	H111—C11—H112	109.467
C5—C4—H41	106.45 (12)	C10ⁱ—C12—C11	110.29 (14)
O8—C4—H41	109.20 (10)	C10ⁱ—C12—H121	109.20 (10)
C4—C5—C6	111.54 (18)	C11—C12—H121	109.10 (10)
C4—C5—H51	108.87 (12)	C10ⁱ—C12—H122	109.40 (10)
C6—C5—H51	108.75 (13)	C11—C12—H122	109.29 (11)
C4—C5—H52	108.92 (14)	H121—C12—H122	109.467
C6—C5—H52	109.27 (14)

Symmetry code: (i) −x, −y, −z.

(CHDdis) 1,4-cyclohexane-1,4-diol (mixed isomers, disordered) top

Crystal data top

2(C₆H₁₂O₂)·C₆H₁₂O₂	F(000) = 384.000
M_r = 348.47	D_x = 1.100 Mg m⁻³
Monoclinic, P2₁/c	Melting point: not measured K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.5263 (3) Å	Cell parameters from 2042 reflections
b = 11.527 (1) Å	θ = 2.3–26.3°
c = 14.2082 (3) Å	µ = 0.08 mm⁻¹
β = 100.123 (6)°	T = 293 K
V = 1052.22 (11) Å³	Prism, colorless
Z = 2	0.50 × 0.35 × 0.22 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.03
Graphite monochromator	θ_max = 26.3°, θ_min = 2.3°
ω/2θ scans	h = −8→8
6016 measured reflections	k = −14→13
2042 independent reflections	l = −16→17
675 reflections with I > 2.00u(I)

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.150	Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]2 21.1 30.8 13.7 2.59
S = 0.91	(Δ/σ)_max = 0.004
675 reflections	Δρ_max = 0.36 e Å⁻³
118 parameters	Δρ_min = −0.14 e Å⁻³

Crystal data top

2(C₆H₁₂O₂)·C₆H₁₂O₂	V = 1052.22 (11) Å³
M_r = 348.47	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.5263 (3) Å	µ = 0.08 mm⁻¹
b = 11.527 (1) Å	T = 293 K
c = 14.2082 (3) Å	0.50 × 0.35 × 0.22 mm
β = 100.123 (6)°

Data collection top

Siemens P4 diffractometer	675 reflections with I > 2.00u(I)
6016 measured reflections	R_int = 0.03
2042 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	118 parameters
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.36 e Å⁻³
675 reflections	Δρ_min = −0.14 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2960 (10)	0.4625 (6)	0.1228 (6)	0.0929
C2	0.1184 (9)	0.5122 (7)	0.1705 (6)	0.1026
C3	0.0879 (11)	0.6359 (7)	0.1559 (6)	0.1051
C4	0.2880 (11)	0.7038 (7)	0.1871 (6)	0.0985
C5	0.4678 (13)	0.6575 (8)	0.1446 (7)	0.1371
C6	0.4984 (9)	0.5290 (7)	0.1607 (7)	0.1233
O7	0.3290 (7)	0.3454 (5)	0.1519 (5)	0.1210
O8	0.3257 (7)	0.7108 (4)	0.2883 (4)	0.0907
O9	−0.0280 (7)	0.2134 (5)	0.0938 (4)	0.0939
C10	0.0042 (9)	0.0933 (6)	0.0709 (5)	0.0759
C11	−0.2002 (9)	0.0355 (6)	0.0269 (5)	0.0735
C12	−0.1615 (9)	−0.0892 (6)	−0.0036 (5)	0.0810
H11	0.2630 (10)	0.4671 (6)	0.0533 (6)	0.1080*
H21	0.1579 (9)	0.5001 (7)	0.2405 (6)	0.1054*
H22	−0.0152 (9)	0.4725 (7)	0.1454 (6)	0.1054*
H31	−0.0221 (11)	0.6647 (7)	0.1882 (6)	0.1194*
H32	0.0507 (11)	0.6492 (7)	0.0846 (6)	0.1194*
H41	0.2809 (11)	0.7871 (7)	0.1700 (6)	0.1150*
H51	0.5945 (13)	0.7033 (8)	0.1694 (7)	0.1486*
H52	0.4238 (13)	0.6735 (8)	0.0739 (7)	0.1486*
H61	0.5361 (9)	0.5158 (7)	0.2302 (7)	0.1229*
H62	0.6134 (9)	0.5051 (7)	0.1273 (7)	0.1229*
H71	0.240 (10)	0.313 (6)	0.135 (5)	0.0750*
H81	0.410 (10)	0.742 (5)	0.315 (5)	0.0750*
H91	−0.100 (10)	0.215 (6)	0.132 (4)	0.0750*
H101	0.0578 (9)	0.0487 (6)	0.1306 (5)	0.0843*
H111	−0.2942 (9)	0.0314 (6)	0.0747 (5)	0.0479*
H112	−0.2720 (9)	0.0740 (6)	−0.0351 (5)	0.0479*
H121	−0.2929 (9)	−0.1295 (6)	−0.0357 (5)	0.0503*
H122	−0.0952 (9)	−0.1359 (6)	0.0612 (5)	0.0503*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.068 (5)	0.085 (5)	0.126 (6)	−0.001 (4)	0.018 (4)	0.002 (5)
C2	0.045 (4)	0.106 (6)	0.151 (7)	0.002 (3)	0.000 (4)	0.008 (5)
C3	0.080 (5)	0.107 (6)	0.120 (6)	0.002 (5)	−0.003 (4)	−0.017 (5)
C4	0.089 (6)	0.095 (5)	0.111 (7)	−0.016 (4)	0.015 (5)	0.001 (5)
C5	0.108 (7)	0.151 (9)	0.162 (8)	−0.048 (6)	0.051 (6)	−0.016 (7)
C6	0.044 (4)	0.108 (7)	0.220 (10)	−0.005 (4)	0.024 (5)	0.019 (7)
O7	0.066 (3)	0.091 (4)	0.190 (6)	0.004 (3)	−0.022 (4)	−0.017 (4)
O8	0.071 (3)	0.102 (4)	0.097 (4)	−0.025 (2)	0.010 (3)	−0.006 (3)
O9	0.083 (3)	0.087 (3)	0.118 (4)	−0.011 (3)	0.036 (3)	−0.018 (3)
C10	0.064 (4)	0.074 (5)	0.093 (5)	−0.006 (3)	0.024 (4)	−0.003 (4)
C11	0.053 (4)	0.088 (5)	0.080 (4)	−0.009 (3)	0.015 (3)	−0.001 (4)
C12	0.060 (4)	0.089 (5)	0.093 (5)	−0.018 (3)	0.009 (4)	−0.004 (4)

Geometric parameters (Å, º) top

C1—C2	1.550 (10)	C5—H52	1.012
C1—C6	1.538 (9)	C6—H61	0.986
C1—O7	1.417 (9)	C6—H62	0.995
C1—H11	0.975	O7—H71	0.67 (6)
C2—C3	1.449 (9)	O8—H81	0.72 (6)
C2—H21	0.993	O9—C10	1.447 (8)
C2—H22	0.994	O9—H91	0.76 (6)
C3—C4	1.521 (9)	C10—C11	1.524 (8)
C3—H31	0.975	C10—C12ⁱ	1.522 (8)
C3—H32	1.011	C10—H101	1.001
C4—C5	1.509 (11)	C11—C12	1.535 (8)
C4—O8	1.418 (8)	C11—H111	0.994
C4—H41	0.989	C11—H112	1.022
C5—C6	1.510 (10)	C12—H121	1.010
C5—H51	0.992	C12—H122	1.089

C2—C1—C6	109.0 (6)	H51—C5—H52	109.144
C2—C1—O7	108.1 (6)	C1—C6—C5	110.7 (6)
C6—C1—O7	107.3 (6)	C1—C6—H61	108.7 (5)
C2—C1—H11	111.8 (4)	C5—C6—H61	107.8 (6)
C6—C1—H11	110.6 (5)	C1—C6—H62	111.5 (4)
O7—C1—H11	110.0 (4)	C5—C6—H62	107.0 (5)
C1—C2—C3	113.3 (7)	H61—C6—H62	111.009
C1—C2—H21	107.6 (4)	C1—O7—H71	111 (6)
C3—C2—H21	106.6 (5)	C4—O8—H81	122 (5)
C1—C2—H22	110.5 (4)	C10—O9—H91	109 (5)
C3—C2—H22	108.2 (4)	O9—C10—C11	111.1 (5)
H21—C2—H22	110.588	O9—C10—C12ⁱ	108.2 (5)
C2—C3—C4	112.1 (6)	C11—C10—C12ⁱ	111.6 (5)
C2—C3—H31	111.2 (5)	O9—C10—H101	110.1 (4)
C4—C3—H31	110.7 (4)	C11—C10—H101	105.9 (4)
C2—C3—H32	107.1 (5)	C12ⁱ—C10—H101	110.0 (4)
C4—C3—H32	104.9 (5)	C10—C11—C12	110.5 (5)
H31—C3—H32	110.599	C10—C11—H111	109.9 (3)
C3—C4—C5	112.9 (7)	C12—C11—H111	107.5 (3)
C3—C4—O8	108.1 (6)	C10—C11—H112	113.5 (4)
C5—C4—O8	114.7 (7)	C12—C11—H112	103.7 (4)
C3—C4—H41	115.3 (4)	H111—C11—H112	111.443
C5—C4—H41	104.6 (5)	C10ⁱ—C12—C11	111.6 (5)
O8—C4—H41	100.8 (4)	C10ⁱ—C12—H121	108.4 (3)
C4—C5—C6	112.3 (7)	C11—C12—H121	112.9 (3)
C4—C5—H51	109.2 (4)	C10ⁱ—C12—H122	107.7 (4)
C6—C5—H51	112.9 (4)	C11—C12—H122	106.6 (4)
C4—C5—H52	103.2 (5)	H121—C12—H122	109.524
C6—C5—H52	109.7 (6)

Symmetry code: (i) −x, −y, −z.

Experimental details

	(CHDct)	(CHDdis)
Crystal data
Chemical formula	2(C₆H₁₂O₂)·C₆H₁₂O₂	2(C₆H₁₂O₂)·C₆H₁₂O₂
M_r	348.47	348.47
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c
Temperature (K)	193	293
a, b, c (Å)	6.453 (2), 11.678 (4), 13.396 (4)	6.5263 (3), 11.527 (1), 14.2082 (3)
β (°)	101.378 (6)	100.123 (6)
V (Å³)	989.7 (6)	1052.22 (11)
Z	2	2
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.09	0.08
Crystal size (mm)	0.20 × 0.14 × 0.12	0.50 × 0.35 × 0.22

Data collection
Diffractometer	Bruker SMART CCD diffractometer	Siemens P4 diffractometer
Absorption correction	–	–
No. of measured, independent and observed reflections	6517, 2331, 1407 [I > 3.00u(I)]	6016, 2042, 675 [I > 2.00u(I)]
R_int	0.07	0.03
(sin θ/λ)_max (Å⁻¹)	0.658	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.119, 1.02	0.068, 0.150, 0.91
No. of reflections	1407	675
No. of parameters	122	118
No. of restraints	?	?
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22	0.36, −0.14

Computer programs: omega scans 0.3deg/frame, 1271 frames, XSCANS (Siemens, 1993), SMART, XSCANS, SAINT, SIR97 (Altomare et al. 1994), CRYSTALS (Watkin et al. 2001), CAMERON (Watkin et al. 1996) Mercury (Bruno, et al. 2002).

Selected geometric parameters (Å, º) for (CHDct) top

C1—C2	1.505 (2)	O7—H71	0.92 (3)
C1—C6	1.513 (3)	O8—H81	0.87 (3)
C1—O7	1.416 (3)	O9—C10	1.441 (2)
C2—C3	1.517 (3)	O9—H91	0.91 (2)
C3—C4	1.522 (3)	C10—C11	1.519 (3)
C4—C5	1.505 (3)	C10—C12ⁱ	1.520 (2)
C4—O8	1.417 (3)	C11—C12	1.526 (2)
C5—C6	1.536 (3)

C2—C1—C6	110.42 (17)	C1—C6—C5	110.97 (19)
C2—C1—O7	111.14 (16)	C1—O7—H71	110.9 (17)
C6—C1—O7	109.16 (18)	C4—O8—H81	107.7 (19)
C1—C2—C3	111.58 (17)	C10—O9—H91	103.7 (13)
C2—C3—C4	112.29 (16)	O9—C10—C11	111.00 (14)
C3—C4—C5	110.75 (19)	O9—C10—C12ⁱ	108.04 (15)
C3—C4—O8	108.26 (18)	C11—C10—C12ⁱ	111.57 (16)
C5—C4—O8	111.92 (19)	C10—C11—C12	110.71 (14)
C4—C5—C6	111.54 (18)	C10ⁱ—C12—C11	110.29 (14)

Symmetry code: (i) −x, −y, −z.

Selected geometric parameters (Å, º) for (CHDdis) top

C1—C2	1.550 (10)	C4—O8	1.418 (8)
C1—C6	1.538 (9)	C5—C6	1.510 (10)
C1—O7	1.417 (9)	O9—C10	1.447 (8)
C2—C3	1.449 (9)	C10—C11	1.524 (8)
C3—C4	1.521 (9)	C10—C12ⁱ	1.522 (8)
C4—C5	1.509 (11)	C11—C12	1.535 (8)

C2—C1—C6	109.0 (6)	C4—C5—C6	112.3 (7)
C2—C1—O7	108.1 (6)	C1—C6—C5	110.7 (6)
C6—C1—O7	107.3 (6)	O9—C10—C11	111.1 (5)
C1—C2—C3	113.3 (7)	O9—C10—C12ⁱ	108.2 (5)
C2—C3—C4	112.1 (6)	C11—C10—C12ⁱ	111.6 (5)
C3—C4—C5	112.9 (7)	C10—C11—C12	110.5 (5)
C3—C4—O8	108.1 (6)	C10ⁱ—C12—C11	111.6 (5)
C5—C4—O8	114.7 (7)

Symmetry code: (i) −x, −y, −z.

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