Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108019460/bk5075sup1.cif
Contains datablocks CHDct, CHDdis

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019460/bk5075CHDctsup2.hkl
Contains datablock CHDct

hkl

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
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
(CHDct) cis-1,4-cyclohexane-1,4-diol-trans-1,4-cyclohexane-1,4-diol (2/1) top
Crystal data top
2(C6H12O2)·C6H12O2F(000) = 384.000
Mr = 348.47Dx = 1.169 Mg m3
Monoclinic, P21/cMelting point: not measured K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.453 (2) ÅCell parameters from 1407 reflections
b = 11.678 (4) Åθ = 2.3–27.9°
c = 13.396 (4) ŵ = 0.09 mm1
β = 101.378 (6)°T = 193 K
V = 989.7 (6) Å3Narrow plate, colorless
Z = 20.20 × 0.14 × 0.12 mm
Data collection top
Bruker SMART CCD
diffractometer
Rint = 0.07
Graphite monochromatorθmax = 27.9°, θmin = 2.3°
ω/2θ scansh = 87
6517 measured reflectionsk = 1514
2331 independent reflectionsl = 1711
1407 reflections with I > 3.00u(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H 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 reflectionsΔρmax = 0.24 e Å3
122 parametersΔρmin = 0.22 e Å3
Crystal data top
2(C6H12O2)·C6H12O2V = 989.7 (6) Å3
Mr = 348.47Z = 2
Monoclinic, P21/cMo Kα radiation
a = 6.453 (2) ŵ = 0.09 mm1
b = 11.678 (4) ÅT = 193 K
c = 13.396 (4) Å0.20 × 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 reflectionsRint = 0.07
2331 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048122 parameters
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.24 e Å3
1407 reflectionsΔρmin = 0.22 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2962 (3)0.45216 (17)0.12641 (16)0.0444
C20.1156 (3)0.50412 (16)0.16674 (16)0.0417
C30.0901 (3)0.63049 (18)0.14109 (19)0.0557
C40.2932 (3)0.69751 (17)0.17767 (16)0.0467
C50.4743 (4)0.6444 (2)0.1387 (2)0.0641
C60.4989 (3)0.5168 (2)0.1662 (2)0.0616
O70.3246 (3)0.33547 (13)0.15463 (15)0.0688
O80.3322 (2)0.70146 (12)0.28547 (11)0.0467
O90.0356 (3)0.21040 (11)0.09600 (13)0.0503
C100.0033 (3)0.09267 (15)0.07315 (15)0.0388
C110.2015 (3)0.03172 (15)0.02757 (15)0.0394
C120.1580 (3)0.09117 (15)0.00105 (15)0.0411
H110.2606 (3)0.45758 (17)0.05045 (16)0.0527
H210.1426 (3)0.49452 (16)0.24238 (16)0.0493
H220.0177 (3)0.46332 (16)0.13554 (16)0.0493
H310.0227 (3)0.66253 (18)0.17456 (19)0.0631
H320.0471 (3)0.63942 (18)0.06559 (19)0.0631
H410.2781 (3)0.77734 (17)0.15019 (16)0.0538
H510.6078 (4)0.6851 (2)0.1698 (2)0.0795
H520.4483 (4)0.6530 (2)0.0629 (2)0.0795
H610.5371 (3)0.5084 (2)0.2419 (2)0.0747
H620.6140 (3)0.4838 (2)0.1349 (2)0.0747
H710.200 (5)0.296 (2)0.137 (2)0.072 (8)
H810.445 (5)0.743 (3)0.306 (2)0.084 (9)
H910.125 (4)0.2054 (18)0.1408 (18)0.053 (6)
H1010.0658 (3)0.05106 (15)0.13927 (15)0.0472
H1110.2956 (3)0.03076 (15)0.07858 (15)0.0486
H1120.2732 (3)0.07362 (15)0.03484 (15)0.0486
H1210.2937 (3)0.12759 (15)0.03534 (15)0.0500
H1220.0971 (3)0.13502 (15)0.06203 (15)0.0500
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0340 (10)0.0455 (11)0.0534 (11)0.0001 (8)0.0078 (8)0.0099 (9)
C20.0295 (9)0.0400 (10)0.0549 (12)0.0009 (7)0.0062 (8)0.0047 (8)
C30.0381 (11)0.0448 (11)0.0759 (15)0.0049 (8)0.0090 (10)0.0010 (10)
C40.0478 (12)0.0352 (9)0.0536 (12)0.0053 (8)0.0018 (9)0.0107 (8)
C50.0617 (15)0.0686 (15)0.0705 (14)0.0247 (12)0.0336 (12)0.0123 (13)
C60.0275 (9)0.0639 (15)0.0944 (18)0.0022 (9)0.0140 (10)0.0253 (12)
O70.0431 (9)0.0391 (8)0.1119 (15)0.0090 (7)0.0148 (9)0.0152 (8)
O80.0454 (8)0.0436 (7)0.0530 (9)0.0132 (6)0.0144 (6)0.0038 (6)
O90.0560 (8)0.0339 (7)0.0676 (9)0.0045 (6)0.0284 (8)0.0093 (6)
C100.0390 (10)0.0304 (9)0.0490 (10)0.0003 (7)0.0124 (8)0.0020 (7)
C110.0380 (10)0.0349 (8)0.0480 (11)0.0013 (7)0.0149 (8)0.0013 (8)
C120.0393 (9)0.0354 (9)0.0513 (11)0.0044 (7)0.0154 (8)0.0017 (8)
Geometric parameters (Å, º) top
C1—C21.505 (2)C5—H521.000
C1—C61.513 (3)C6—H611.000
C1—O71.416 (3)C6—H621.000
C1—H111.000O7—H710.92 (3)
C2—C31.517 (3)O8—H810.87 (3)
C2—H211.000O9—C101.441 (2)
C2—H221.000O9—H910.91 (2)
C3—C41.522 (3)C10—C111.519 (3)
C3—H311.000C10—C12i1.520 (2)
C3—H321.000C10—H1011.021
C4—C51.505 (3)C11—C121.526 (2)
C4—O81.417 (3)C11—H1111.000
C4—H411.000C11—H1121.000
C5—C61.536 (3)C12—H1211.000
C5—H511.000C12—H1221.000
C2—C1—C6110.42 (17)H51—C5—H52109.465
C2—C1—O7111.14 (16)C1—C6—C5110.97 (19)
C6—C1—O7109.16 (18)C1—C6—H61109.37 (14)
C2—C1—H11107.53 (11)C5—C6—H61109.39 (14)
C6—C1—H11109.65 (14)C1—C6—H62108.77 (11)
O7—C1—H11108.91 (11)C5—C6—H62108.85 (12)
C1—C2—C3111.58 (17)H61—C6—H62109.464
C1—C2—H21109.05 (11)C1—O7—H71110.9 (17)
C3—C2—H21109.15 (12)C4—O8—H81107.7 (19)
C1—C2—H22108.70 (10)C10—O9—H91103.7 (13)
C3—C2—H22108.85 (11)O9—C10—C11111.00 (14)
H21—C2—H22109.468O9—C10—C12i108.04 (15)
C2—C3—C4112.29 (16)C11—C10—C12i111.57 (16)
C2—C3—H31108.57 (12)O9—C10—H101108.99 (11)
C4—C3—H31108.66 (13)C11—C10—H101106.80 (10)
C2—C3—H32109.06 (12)C12i—C10—H101110.40 (10)
C4—C3—H32108.75 (12)C10—C11—C12110.71 (14)
H31—C3—H32109.462C10—C11—H111109.20 (10)
C3—C4—C5110.75 (19)C12—C11—H111109.13 (9)
C3—C4—O8108.26 (18)C10—C11—H112109.20 (10)
C5—C4—O8111.92 (19)C12—C11—H112109.14 (11)
C3—C4—H41110.19 (11)H111—C11—H112109.467
C5—C4—H41106.45 (12)C10i—C12—C11110.29 (14)
O8—C4—H41109.20 (10)C10i—C12—H121109.20 (10)
C4—C5—C6111.54 (18)C11—C12—H121109.10 (10)
C4—C5—H51108.87 (12)C10i—C12—H122109.40 (10)
C6—C5—H51108.75 (13)C11—C12—H122109.29 (11)
C4—C5—H52108.92 (14)H121—C12—H122109.467
C6—C5—H52109.27 (14)
Symmetry code: (i) x, y, z.
(CHDdis) 1,4-cyclohexane-1,4-diol (mixed isomers, disordered) top
Crystal data top
2(C6H12O2)·C6H12O2F(000) = 384.000
Mr = 348.47Dx = 1.100 Mg m3
Monoclinic, P21/cMelting point: not measured K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.5263 (3) ÅCell parameters from 2042 reflections
b = 11.527 (1) Åθ = 2.3–26.3°
c = 14.2082 (3) ŵ = 0.08 mm1
β = 100.123 (6)°T = 293 K
V = 1052.22 (11) Å3Prism, colorless
Z = 20.50 × 0.35 × 0.22 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.03
Graphite monochromatorθmax = 26.3°, θmin = 2.3°
ω/2θ scansh = 88
6016 measured reflectionsk = 1413
2042 independent reflectionsl = 1617
675 reflections with I > 2.00u(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H 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 reflectionsΔρmax = 0.36 e Å3
118 parametersΔρmin = 0.14 e Å3
Crystal data top
2(C6H12O2)·C6H12O2V = 1052.22 (11) Å3
Mr = 348.47Z = 2
Monoclinic, P21/cMo Kα radiation
a = 6.5263 (3) ŵ = 0.08 mm1
b = 11.527 (1) ÅT = 293 K
c = 14.2082 (3) Å0.50 × 0.35 × 0.22 mm
β = 100.123 (6)°
Data collection top
Siemens P4
diffractometer
675 reflections with I > 2.00u(I)
6016 measured reflectionsRint = 0.03
2042 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.068118 parameters
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 0.91Δρmax = 0.36 e Å3
675 reflectionsΔρmin = 0.14 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2960 (10)0.4625 (6)0.1228 (6)0.0929
C20.1184 (9)0.5122 (7)0.1705 (6)0.1026
C30.0879 (11)0.6359 (7)0.1559 (6)0.1051
C40.2880 (11)0.7038 (7)0.1871 (6)0.0985
C50.4678 (13)0.6575 (8)0.1446 (7)0.1371
C60.4984 (9)0.5290 (7)0.1607 (7)0.1233
O70.3290 (7)0.3454 (5)0.1519 (5)0.1210
O80.3257 (7)0.7108 (4)0.2883 (4)0.0907
O90.0280 (7)0.2134 (5)0.0938 (4)0.0939
C100.0042 (9)0.0933 (6)0.0709 (5)0.0759
C110.2002 (9)0.0355 (6)0.0269 (5)0.0735
C120.1615 (9)0.0892 (6)0.0036 (5)0.0810
H110.2630 (10)0.4671 (6)0.0533 (6)0.1080*
H210.1579 (9)0.5001 (7)0.2405 (6)0.1054*
H220.0152 (9)0.4725 (7)0.1454 (6)0.1054*
H310.0221 (11)0.6647 (7)0.1882 (6)0.1194*
H320.0507 (11)0.6492 (7)0.0846 (6)0.1194*
H410.2809 (11)0.7871 (7)0.1700 (6)0.1150*
H510.5945 (13)0.7033 (8)0.1694 (7)0.1486*
H520.4238 (13)0.6735 (8)0.0739 (7)0.1486*
H610.5361 (9)0.5158 (7)0.2302 (7)0.1229*
H620.6134 (9)0.5051 (7)0.1273 (7)0.1229*
H710.240 (10)0.313 (6)0.135 (5)0.0750*
H810.410 (10)0.742 (5)0.315 (5)0.0750*
H910.100 (10)0.215 (6)0.132 (4)0.0750*
H1010.0578 (9)0.0487 (6)0.1306 (5)0.0843*
H1110.2942 (9)0.0314 (6)0.0747 (5)0.0479*
H1120.2720 (9)0.0740 (6)0.0351 (5)0.0479*
H1210.2929 (9)0.1295 (6)0.0357 (5)0.0503*
H1220.0952 (9)0.1359 (6)0.0612 (5)0.0503*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.068 (5)0.085 (5)0.126 (6)0.001 (4)0.018 (4)0.002 (5)
C20.045 (4)0.106 (6)0.151 (7)0.002 (3)0.000 (4)0.008 (5)
C30.080 (5)0.107 (6)0.120 (6)0.002 (5)0.003 (4)0.017 (5)
C40.089 (6)0.095 (5)0.111 (7)0.016 (4)0.015 (5)0.001 (5)
C50.108 (7)0.151 (9)0.162 (8)0.048 (6)0.051 (6)0.016 (7)
C60.044 (4)0.108 (7)0.220 (10)0.005 (4)0.024 (5)0.019 (7)
O70.066 (3)0.091 (4)0.190 (6)0.004 (3)0.022 (4)0.017 (4)
O80.071 (3)0.102 (4)0.097 (4)0.025 (2)0.010 (3)0.006 (3)
O90.083 (3)0.087 (3)0.118 (4)0.011 (3)0.036 (3)0.018 (3)
C100.064 (4)0.074 (5)0.093 (5)0.006 (3)0.024 (4)0.003 (4)
C110.053 (4)0.088 (5)0.080 (4)0.009 (3)0.015 (3)0.001 (4)
C120.060 (4)0.089 (5)0.093 (5)0.018 (3)0.009 (4)0.004 (4)
Geometric parameters (Å, º) top
C1—C21.550 (10)C5—H521.012
C1—C61.538 (9)C6—H610.986
C1—O71.417 (9)C6—H620.995
C1—H110.975O7—H710.67 (6)
C2—C31.449 (9)O8—H810.72 (6)
C2—H210.993O9—C101.447 (8)
C2—H220.994O9—H910.76 (6)
C3—C41.521 (9)C10—C111.524 (8)
C3—H310.975C10—C12i1.522 (8)
C3—H321.011C10—H1011.001
C4—C51.509 (11)C11—C121.535 (8)
C4—O81.418 (8)C11—H1110.994
C4—H410.989C11—H1121.022
C5—C61.510 (10)C12—H1211.010
C5—H510.992C12—H1221.089
C2—C1—C6109.0 (6)H51—C5—H52109.144
C2—C1—O7108.1 (6)C1—C6—C5110.7 (6)
C6—C1—O7107.3 (6)C1—C6—H61108.7 (5)
C2—C1—H11111.8 (4)C5—C6—H61107.8 (6)
C6—C1—H11110.6 (5)C1—C6—H62111.5 (4)
O7—C1—H11110.0 (4)C5—C6—H62107.0 (5)
C1—C2—C3113.3 (7)H61—C6—H62111.009
C1—C2—H21107.6 (4)C1—O7—H71111 (6)
C3—C2—H21106.6 (5)C4—O8—H81122 (5)
C1—C2—H22110.5 (4)C10—O9—H91109 (5)
C3—C2—H22108.2 (4)O9—C10—C11111.1 (5)
H21—C2—H22110.588O9—C10—C12i108.2 (5)
C2—C3—C4112.1 (6)C11—C10—C12i111.6 (5)
C2—C3—H31111.2 (5)O9—C10—H101110.1 (4)
C4—C3—H31110.7 (4)C11—C10—H101105.9 (4)
C2—C3—H32107.1 (5)C12i—C10—H101110.0 (4)
C4—C3—H32104.9 (5)C10—C11—C12110.5 (5)
H31—C3—H32110.599C10—C11—H111109.9 (3)
C3—C4—C5112.9 (7)C12—C11—H111107.5 (3)
C3—C4—O8108.1 (6)C10—C11—H112113.5 (4)
C5—C4—O8114.7 (7)C12—C11—H112103.7 (4)
C3—C4—H41115.3 (4)H111—C11—H112111.443
C5—C4—H41104.6 (5)C10i—C12—C11111.6 (5)
O8—C4—H41100.8 (4)C10i—C12—H121108.4 (3)
C4—C5—C6112.3 (7)C11—C12—H121112.9 (3)
C4—C5—H51109.2 (4)C10i—C12—H122107.7 (4)
C6—C5—H51112.9 (4)C11—C12—H122106.6 (4)
C4—C5—H52103.2 (5)H121—C12—H122109.524
C6—C5—H52109.7 (6)
Symmetry code: (i) x, y, z.

Experimental details

(CHDct)(CHDdis)
Crystal data
Chemical formula2(C6H12O2)·C6H12O22(C6H12O2)·C6H12O2
Mr348.47348.47
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)193293
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)
V3)989.7 (6)1052.22 (11)
Z22
Radiation typeMo KαMo Kα
µ (mm1)0.090.08
Crystal size (mm)0.20 × 0.14 × 0.120.50 × 0.35 × 0.22
Data collection
DiffractometerBruker 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)]
Rint0.070.03
(sin θ/λ)max1)0.6580.623
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.119, 1.02 0.068, 0.150, 0.91
No. of reflections1407675
No. of parameters122118
No. of restraints??
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.220.36, 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—C21.505 (2)O7—H710.92 (3)
C1—C61.513 (3)O8—H810.87 (3)
C1—O71.416 (3)O9—C101.441 (2)
C2—C31.517 (3)O9—H910.91 (2)
C3—C41.522 (3)C10—C111.519 (3)
C4—C51.505 (3)C10—C12i1.520 (2)
C4—O81.417 (3)C11—C121.526 (2)
C5—C61.536 (3)
C2—C1—C6110.42 (17)C1—C6—C5110.97 (19)
C2—C1—O7111.14 (16)C1—O7—H71110.9 (17)
C6—C1—O7109.16 (18)C4—O8—H81107.7 (19)
C1—C2—C3111.58 (17)C10—O9—H91103.7 (13)
C2—C3—C4112.29 (16)O9—C10—C11111.00 (14)
C3—C4—C5110.75 (19)O9—C10—C12i108.04 (15)
C3—C4—O8108.26 (18)C11—C10—C12i111.57 (16)
C5—C4—O8111.92 (19)C10—C11—C12110.71 (14)
C4—C5—C6111.54 (18)C10i—C12—C11110.29 (14)
Symmetry code: (i) x, y, z.
Selected geometric parameters (Å, º) for (CHDdis) top
C1—C21.550 (10)C4—O81.418 (8)
C1—C61.538 (9)C5—C61.510 (10)
C1—O71.417 (9)O9—C101.447 (8)
C2—C31.449 (9)C10—C111.524 (8)
C3—C41.521 (9)C10—C12i1.522 (8)
C4—C51.509 (11)C11—C121.535 (8)
C2—C1—C6109.0 (6)C4—C5—C6112.3 (7)
C2—C1—O7108.1 (6)C1—C6—C5110.7 (6)
C6—C1—O7107.3 (6)O9—C10—C11111.1 (5)
C1—C2—C3113.3 (7)O9—C10—C12i108.2 (5)
C2—C3—C4112.1 (6)C11—C10—C12i111.6 (5)
C3—C4—C5112.9 (7)C10—C11—C12110.5 (5)
C3—C4—O8108.1 (6)C10i—C12—C11111.6 (5)
C5—C4—O8114.7 (7)
Symmetry code: (i) x, y, z.
 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds