Solid-state compounds of stereoisomers: cis and trans isomers of 1,2-cyclohexanediol and 2,3-tetralindiol

The phases of 1,2,3,4-tetrahydro-2,3-naphthalenediol (or 2,3-tetralindiol) and of 1,2-cyclohexanediol have been investigated. The structure of a very stable 1:1 compound (or co-crystal) of the cis and trans isomers of 2,3-tetralindiol, the existence of which has been known for nearly a century, has finally been determined. No evidence of any analogous compound between the cis and trans isomers of 1,2-cyclohexanediol has been found. The formation of solid-state compounds of stereoisomers is rare; it probably occurs only if the crystal packing of at least one of the isomers is unfavorable, e.g. if at least one of the melting points is lower than expected. Compound formation is usually unlikely because of the difficulty of simultaneously optimizing the translational spacings for both isomers, but that packing problem is avoided in the cis/trans compound of 2,3-tetralindiol because the two isomers are in very similar environments. In the structures of the individual 2,3-tetralindiol isomers there are clear conflicts between the competing packing requirements of the 1,2-diol moiety and the aromatic ring system; these conflicts are resolved better in the co-crystal than in the structures of the individual isomers.

Computing details

Data collection: APEX2 (Bruker-Nonius, 2004) for 1:1cis/trans-2,3-TD, S,S-2,3-TD; COLLECT (Nonius, 1999) for k99104, k99103, cis-1,2-CHD, k99096, trans-1,2-CHD_1, k99093, trans-1,2-CHD_2, k99095, R,R-1,2-CHD, k99094. Cell refinement: Saintplus in APEX2 (Bruker-Nonius,2004) for 1:1cis/trans-2,3-TD, S,S-2,3-TD; SCALEPACK (Otwinowski & Minor, 1997) for k99104, k99103, cis-1,2-CHD, k99096, trans-1,2-CHD_1, k99093, trans-1,2-CHD_2, k99095, R,R-1,2-CHD, k99094. Data reduction: Saintplus in APEX2 (Bruker-Nonius,2004) for 1:1cis/trans-2,3-TD, S,S-2,3-TD; DENZO-SMN (Otwinowski & Minor, 1997) for k99104, k99103, cis-1,2-CHD, k99096, trans-1,2-CHD_1, k99093, trans-1,2-CHD_2, k99095, R,R-1,2-CHD, k99094. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for 1:1cis/trans-2,3-TD, S,S-2,3-TD; SHELXS97 (Sheldrick, 1997a) for k99104, k99103, cis-1,2-CHD, k99096, trans-1,2-CHD_1, k99093, trans-1,2-CHD_2, k99095, R,R-1,2-CHD, k99094. Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for 1:1cis/trans-2,3-TD, S,S-2,3-TD; SHELXL97 (Sheldrick, 1997b) for k99104, k99103, cis-1,2-CHD, k99096, trans-1,2-CHD_1, k99093, trans-1,2-CHD_2, k99095, R,R-1,2-CHD, k99094. Molecular graphics: XP in SHELXTL (Sheldrick, 1994), Mercury (Macrae et al., 2006) for 1:1cis/trans-2,3-TD; Mercury (Macrae et al., 2006) for S,S-2,3-TD, k99104, k99103, cis-1,2-CHD, k99096, trans-1,2-CHD_1, k99093, trans-1,2-CHD_2, k99095, R,R-1,2-CHD; # XP in Siemens SHELXTL (Sheldrick, 1994); Mercury (Macrae et al., 2006) for k99094. Software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures for 1:1cis/trans-2,3-TD, S,S-2,3-TD; SHELXL97 (Sheldrick, 1997) and local procedures for k99104, k99103, cis-1,2-CHD, k99096, trans-1,2-CHD_1, k99093, trans-1,2-CHD_2, k99095, R,R-1,2-CHD, k99094.

Figures

(1:1cis/trans-2,3-TD) cis-1,2,3,4-tetrahydro-2,3-naphthalenediol trans-1,2,3,4-tetrahydro-2,3-naphthalenediol

Crystal data

(C10H12O2)·(C10H12O2)	F(000) = 696
Mr = 328.40	Dx = 1.311 Mg m^−3
Monoclinic, C2	Melting point = 413–415 K
a = 23.2312 (13) Å	Cu Kα radiation, λ = 1.54178 Å
b = 4.9750 (4) Å	µ = 0.73 mm^−1
c = 15.484 (2) Å	T = 90 K
β = 112.53 (1)°	Thin blade. Largest faces {001}; elongated along [010]., colorless
V = 1653.1 (3) Å^3	0.30 × 0.05 × 0.02 mm
Z = 4

Data collection

Bruker-Nonius X8 Proteum diffractometer	2316 independent reflections
Radiation source: fine-focus rotating anode	2226 reflections with I > 2σ(I)
Graded multi-layer optics monochromator	Rint = 0.116
Detector resolution: 18 pixels mm^-1	θmax = 66.4°, θmin = 3.1°
ω and ϕ scans	h = 0→27
Absorption correction: multi-scan SADABS in APEX2 (Bruker-Nonius, 2004)	k = −5→0
Tmin = 0.810, Tmax = 0.986	l = −17→16
10614 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.229	H-atom parameters constrained
S = 1.18	w = 1/[σ^2(Fo^2) + (0.111P)^2 + 7.930P] where P = (Fo^2 + 2Fc^2)/3
2316 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.44 e Å^−3
1 restraint	Δρmin = −0.48 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.17420 (18)	0.7387 (10)	0.5500 (2)	0.0164 (10)
H01A	0.1801	0.5808	0.5708	0.025*
O2A	0.0596 (3)	0.4990 (18)	0.4429 (5)	0.019 (2)	0.609 (10)
O3A	0.0565 (4)	0.959 (3)	0.4347 (7)	0.019 (3)	0.391 (10)
C1A	0.1755 (2)	0.9758 (16)	0.4188 (4)	0.0183 (15)
H1EA	0.2207	0.9499	0.4348	0.022*
H1AA	0.1706	1.1321	0.4549	0.022*
C2A	0.1505 (2)	0.7326 (15)	0.4485 (4)	0.0171 (13)
H2AA	0.1668	0.5686	0.4283	0.020*
C3A	0.0802 (2)	0.7225 (16)	0.4084 (4)	0.0174 (13)
H3AA	0.0632	0.8831	0.4236	0.021*	0.609 (10)
H3EA	0.0665	0.5653	0.4307	0.021*	0.391 (10)
C4A	0.0570 (2)	0.7117 (14)	0.3013 (4)	0.0124 (12)
H4AA	0.0656	0.5307	0.2824	0.015*
H4EA	0.0113	0.7381	0.2746	0.015*
C5A	0.0867 (2)	0.9202 (14)	0.2602 (4)	0.0150 (14)
C6A	0.0592 (2)	0.9971 (15)	0.1684 (4)	0.0153 (14)
H6A	0.0200	0.9206	0.1311	0.018*
C7A	0.0856 (2)	1.1801 (16)	0.1278 (4)	0.0188 (16)
H7A	0.0652	1.2267	0.0637	0.023*
C8A	0.1431 (3)	1.2966 (15)	0.1825 (4)	0.0212 (16)
H8A	0.1623	1.4231	0.1561	0.025*
C9A	0.1713 (2)	1.2234 (16)	0.2761 (4)	0.0169 (14)
H9A	0.2101	1.3025	0.3136	0.020*
C10A	0.1448 (2)	1.0400 (13)	0.3159 (4)	0.0112 (13)
O1B	0.18485 (19)	0.2357 (11)	0.6342 (3)	0.0196 (10)
H01B	0.1829	0.0810	0.6116	0.029*
O2B	0.0681 (3)	0.4622 (16)	0.6250 (5)	0.018 (2)	0.609 (10)
O3B	0.0685 (4)	0.006 (2)	0.6159 (7)	0.011 (3)	0.391 (10)
C1B	0.1927 (2)	0.4779 (15)	0.7708 (4)	0.0179 (14)
H1EB	0.2383	0.4562	0.8032	0.021*
H1AB	0.1851	0.6348	0.7286	0.021*
C2B	0.1658 (2)	0.2256 (16)	0.7120 (4)	0.0139 (13)
H2AB	0.1829	0.0605	0.7500	0.017*
C3B	0.0942 (2)	0.2286 (16)	0.6782 (4)	0.0160 (13)
H3EB	0.0801	0.0684	0.6415	0.019*	0.609 (10)
H3AB	0.0775	0.3906	0.6443	0.019*	0.391 (10)
C4B	0.0760 (2)	0.2073 (16)	0.7615 (4)	0.0183 (14)
H4AB	0.0869	0.0261	0.7894	0.022*
H4EB	0.0303	0.2294	0.7406	0.022*
C5B	0.1085 (2)	0.4190 (13)	0.8357 (4)	0.0141 (14)
C6B	0.0831 (3)	0.4967 (15)	0.8996 (4)	0.0179 (14)
H6B	0.0443	0.4215	0.8944	0.021*
C7B	0.1121 (3)	0.6809 (15)	0.9709 (4)	0.0192 (15)
H7B	0.0943	0.7280	1.0147	0.023*
C8B	0.1673 (3)	0.7916 (14)	0.9758 (4)	0.0173 (16)
H8B	0.1879	0.9171	1.0240	0.021*
C9B	0.1936 (3)	0.7258 (17)	0.9126 (4)	0.0205 (14)
H9B	0.2311	0.8102	0.9163	0.025*
C10B	0.1649 (2)	0.5337 (14)	0.8427 (4)	0.0146 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0268 (19)	0.012 (2)	0.0096 (18)	−0.006 (2)	0.0065 (16)	0.001 (2)
O2A	0.031 (4)	0.013 (5)	0.018 (4)	0.001 (4)	0.014 (3)	0.005 (4)
O3A	0.016 (5)	0.036 (9)	0.006 (5)	0.012 (6)	0.004 (4)	0.000 (5)
C1A	0.020 (3)	0.023 (4)	0.010 (3)	−0.003 (3)	0.002 (2)	0.000 (3)
C2A	0.027 (3)	0.012 (4)	0.011 (3)	−0.003 (3)	0.004 (2)	0.002 (3)
C3A	0.019 (3)	0.010 (4)	0.023 (3)	−0.003 (3)	0.009 (2)	0.005 (3)
C4A	0.012 (2)	0.008 (3)	0.015 (3)	0.001 (3)	0.002 (2)	0.003 (3)
C5A	0.015 (2)	0.016 (4)	0.015 (3)	0.004 (3)	0.007 (2)	0.000 (3)
C6A	0.013 (2)	0.019 (4)	0.011 (3)	−0.001 (3)	0.001 (2)	−0.007 (3)
C7A	0.019 (3)	0.022 (5)	0.013 (3)	0.007 (3)	0.004 (2)	0.004 (3)
C8A	0.027 (3)	0.021 (4)	0.026 (3)	0.002 (3)	0.020 (3)	0.004 (3)
C9A	0.020 (3)	0.018 (4)	0.015 (3)	−0.003 (3)	0.009 (2)	−0.003 (3)
C10A	0.013 (2)	0.009 (3)	0.011 (3)	0.004 (2)	0.005 (2)	0.002 (2)
O1B	0.031 (2)	0.015 (3)	0.018 (2)	−0.002 (2)	0.0146 (17)	−0.003 (2)
O2B	0.024 (3)	0.012 (4)	0.014 (4)	0.000 (3)	0.001 (3)	0.000 (3)
O3B	0.018 (5)	0.008 (6)	0.010 (5)	−0.003 (5)	0.009 (4)	−0.002 (5)
C1B	0.024 (3)	0.017 (4)	0.017 (3)	−0.009 (3)	0.012 (2)	−0.003 (3)
C2B	0.022 (3)	0.010 (4)	0.013 (3)	0.000 (3)	0.011 (2)	0.000 (3)
C3B	0.020 (3)	0.011 (3)	0.014 (3)	−0.001 (3)	0.003 (2)	0.000 (3)
C4B	0.022 (3)	0.011 (4)	0.025 (3)	0.000 (3)	0.012 (2)	0.002 (3)
C5B	0.022 (3)	0.004 (4)	0.017 (3)	0.002 (3)	0.009 (2)	0.002 (3)
C6B	0.022 (3)	0.018 (4)	0.018 (3)	0.002 (3)	0.012 (2)	0.000 (3)
C7B	0.028 (3)	0.015 (4)	0.015 (3)	0.002 (3)	0.009 (2)	−0.003 (3)
C8B	0.029 (3)	0.011 (4)	0.006 (3)	0.006 (3)	0.000 (2)	−0.004 (3)
C9B	0.024 (3)	0.018 (4)	0.016 (3)	−0.004 (3)	0.003 (2)	0.001 (3)
C10B	0.016 (2)	0.016 (4)	0.011 (3)	0.003 (3)	0.005 (2)	0.005 (3)

Geometric parameters (Å, º)

O1A—C2A	1.453 (6)	O1B—C2B	1.434 (6)
O1A—H01A	0.8400	O1B—H01B	0.8400
O2A—C3A	1.396 (11)	O2B—C3B	1.419 (10)
O2A—H3EA	0.4391	O2B—H3AB	0.4624
O3A—C3A	1.423 (14)	O3B—C3B	1.440 (13)
O3A—H3AA	0.4661	O3B—H3EB	0.4957
C1A—C2A	1.490 (10)	C1B—C10B	1.511 (7)
C1A—C10A	1.509 (7)	C1B—C2B	1.536 (10)
C1A—H1EA	0.9900	C1B—H1EB	0.9900
C1A—H1AA	0.9900	C1B—H1AB	0.9900
C2A—C3A	1.508 (7)	C2B—C3B	1.541 (7)
C2A—H2AA	1.0000	C2B—H2AB	1.0000
C3A—C4A	1.536 (8)	C3B—C4B	1.507 (8)
C3A—H3AA	0.9596	C3B—H3EB	0.9600
C3A—H3EA	0.9582	C3B—H3AB	0.9587
C4A—C5A	1.515 (8)	C4B—C5B	1.529 (9)
C4A—H4AA	0.9900	C4B—H4AB	0.9900
C4A—H4EA	0.9900	C4B—H4EB	0.9900
C5A—C6A	1.371 (8)	C5B—C6B	1.388 (8)
C5A—C10A	1.423 (8)	C5B—C10B	1.393 (8)
C6A—C7A	1.378 (9)	C6B—C7B	1.395 (9)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.404 (9)	C7B—C8B	1.370 (9)
C7A—H7A	0.9500	C7B—H7B	0.9500
C8A—C9A	1.392 (8)	C8B—C9B	1.376 (8)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.373 (9)	C9B—C10B	1.406 (9)
C9A—H9A	0.9500	C9B—H9B	0.9500
C2A—O1A—H01A	109.5	C2B—O1B—H01B	109.5
C3A—O2A—H3EA	4.1	C3B—O2B—H3AB	4.7
C3A—O3A—H3AA	4.5	C3B—O3B—H3EB	11.6
C2A—C1A—C10A	114.5 (5)	C10B—C1B—C2B	113.3 (5)
C2A—C1A—H1EA	108.6	C10B—C1B—H1EB	108.9
C10A—C1A—H1EA	108.6	C2B—C1B—H1EB	108.9
C2A—C1A—H1AA	108.6	C10B—C1B—H1AB	108.9
C10A—C1A—H1AA	108.6	C2B—C1B—H1AB	108.9
H1EA—C1A—H1AA	107.6	H1EB—C1B—H1AB	107.7
O1A—C2A—C1A	106.6 (5)	O1B—C2B—C1B	106.5 (5)
O1A—C2A—C3A	110.4 (5)	O1B—C2B—C3B	110.8 (4)
C1A—C2A—C3A	112.9 (5)	C1B—C2B—C3B	109.5 (5)
O1A—C2A—H2AA	108.9	O1B—C2B—H2AB	110.0
C1A—C2A—H2AA	108.9	C1B—C2B—H2AB	110.0
C3A—C2A—H2AA	108.9	C3B—C2B—H2AB	110.0
O2A—C3A—O3A	108.7 (6)	O2B—C3B—O3B	105.5 (5)
O2A—C3A—C2A	110.2 (6)	O2B—C3B—C4B	110.9 (6)
O3A—C3A—C2A	109.4 (7)	O3B—C3B—C4B	109.8 (6)
O2A—C3A—C4A	110.8 (6)	O2B—C3B—C2B	111.7 (6)
O3A—C3A—C4A	108.9 (6)	O3B—C3B—C2B	109.6 (6)
C2A—C3A—C4A	108.8 (4)	C4B—C3B—C2B	109.2 (4)
O2A—C3A—H3AA	109.6	O2B—C3B—H3EB	111.4
O3A—C3A—H3AA	2.2	O3B—C3B—H3EB	6.0
C2A—C3A—H3AA	110.6	C4B—C3B—H3EB	107.7
C4A—C3A—H3AA	106.7	C2B—C3B—H3EB	105.8
O2A—C3A—H3EA	1.9	O2B—C3B—H3AB	2.2
O3A—C3A—H3EA	110.5	O3B—C3B—H3AB	107.7
C2A—C3A—H3EA	109.7	C4B—C3B—H3AB	109.9
C4A—C3A—H3EA	109.5	C2B—C3B—H3AB	110.5
H3AA—C3A—H3EA	111.4	H3EB—C3B—H3AB	113.6
C5A—C4A—C3A	113.7 (5)	C3B—C4B—C5B	112.0 (5)
C5A—C4A—H4AA	108.8	C3B—C4B—H4AB	109.2
C3A—C4A—H4AA	108.8	C5B—C4B—H4AB	109.2
C5A—C4A—H4EA	108.8	C3B—C4B—H4EB	109.2
C3A—C4A—H4EA	108.8	C5B—C4B—H4EB	109.2
H4AA—C4A—H4EA	107.7	H4AB—C4B—H4EB	107.9
C6A—C5A—C10A	118.0 (6)	C6B—C5B—C10B	118.4 (6)
C6A—C5A—C4A	121.3 (5)	C6B—C5B—C4B	120.3 (5)
C10A—C5A—C4A	120.7 (5)	C10B—C5B—C4B	121.3 (5)
C5A—C6A—C7A	123.0 (5)	C5B—C6B—C7B	122.6 (6)
C5A—C6A—H6A	118.5	C5B—C6B—H6B	118.7
C7A—C6A—H6A	118.5	C7B—C6B—H6B	118.7
C6A—C7A—C8A	119.0 (5)	C8B—C7B—C6B	117.8 (5)
C6A—C7A—H7A	120.5	C8B—C7B—H7B	121.1
C8A—C7A—H7A	120.5	C6B—C7B—H7B	121.1
C9A—C8A—C7A	118.7 (6)	C7B—C8B—C9B	121.7 (6)
C9A—C8A—H8A	120.6	C7B—C8B—H8B	119.1
C7A—C8A—H8A	120.6	C9B—C8B—H8B	119.1
C10A—C9A—C8A	121.8 (5)	C8B—C9B—C10B	120.1 (6)
C10A—C9A—H9A	119.1	C8B—C9B—H9B	120.0
C8A—C9A—H9A	119.1	C10B—C9B—H9B	120.0
C9A—C10A—C5A	119.4 (5)	C5B—C10B—C9B	119.5 (5)
C9A—C10A—C1A	120.1 (5)	C5B—C10B—C1B	121.4 (5)
C5A—C10A—C1A	120.4 (5)	C9B—C10B—C1B	118.8 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H01A···O1B	0.84	1.96	2.788 (7)	169
O1B—H01B···O1A^i	0.84	1.92	2.762 (7)	175

Symmetry code: (i) x, y−1, z.

(S,S-2,3-TD) 1,2,3,4-tetrahydro-(S,S)-2,3-naphthalenediol

Crystal data

C10H12O2	F(000) = 352
Mr = 164.20	Dx = 1.327 Mg m^−3
Monoclinic, P21	Melting point: 425 K
a = 5.8751 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 27.9972 (8) Å	µ = 0.74 mm^−1
c = 5.0132 (2) Å	T = 90 K
β = 94.528 (1)°	Block, colorless
V = 822.03 (5) Å^3	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection

Bruker-Nonius X8 Proteum diffractometer	2869 independent reflections
Radiation source: fine-focus rotating anode	2859 reflections with I > 2σ(I)
Graded multi-layer optics monochromator	Rint = 0.029
Detector resolution: 18 pixels mm^-1	θmax = 68.0°, θmin = 3.2°
ω and ϕ scans	h = −7→7
Absorption correction: multi-scan SADABS in APEX2 (Bruker-Nonius, 2004)	k = −33→33
Tmin = 0.916, Tmax = 0.943	l = −5→5
9460 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 0.1143P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.087	(Δ/σ)max < 0.001
S = 1.12	Δρmax = 0.28 e Å^−3
2869 reflections	Δρmin = −0.30 e Å^−3
222 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.052 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (13)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	−0.05563 (16)	0.29675 (4)	0.4484 (2)	0.0177 (2)
H01A	−0.0110	0.2844	0.5961	0.026*
O2A	0.28553 (18)	0.35953 (4)	0.2766 (2)	0.0226 (3)
H02A	0.3255	0.3307	0.2880	0.034*
C1A	−0.2002 (3)	0.35989 (5)	0.7237 (3)	0.0174 (3)
H1EA	−0.3604	0.3490	0.6927	0.021*
1AA	−0.1293	0.3422	0.8799	0.021*
C2A	−0.0734 (2)	0.34795 (5)	0.4790 (3)	0.0161 (3)
H2AA	−0.1635	0.3609	0.3175	0.019*
C3A	0.1601 (2)	0.37157 (5)	0.4985 (3)	0.0179 (3)
H3AA	0.2478	0.3613	0.6678	0.021*
C4A	0.1326 (2)	0.42554 (5)	0.4999 (3)	0.0180 (3)
H4EA	0.2835	0.4403	0.5476	0.022*
H4AA	0.0802	0.4363	0.3171	0.022*
C5A	−0.0346 (3)	0.44322 (5)	0.6931 (3)	0.0178 (3)
C6A	−0.0313 (3)	0.49104 (6)	0.7738 (3)	0.0218 (3)
H6A	0.0808	0.5119	0.7127	0.026*
C7A	−0.1884 (3)	0.50847 (5)	0.9412 (3)	0.0226 (3)
H7A	−0.1834	0.5410	0.9943	0.027*
C8A	−0.3537 (3)	0.47814 (6)	1.0314 (3)	0.0213 (3)
H8A	−0.4634	0.4901	1.1440	0.026*
C9A	−0.3577 (3)	0.43053 (5)	0.9564 (3)	0.0191 (3)
H9A	−0.4694	0.4098	1.0199	0.023*
C10A	−0.1986 (2)	0.41264 (5)	0.7878 (3)	0.0167 (3)
O1B	0.09603 (17)	0.26199 (4)	−0.0450 (2)	0.0199 (2)
H01B	0.0663	0.2737	0.1025	0.030*
O2B	0.49760 (18)	0.26772 (4)	0.2940 (2)	0.0204 (3)
H02B	0.6341	0.2719	0.3524	0.031*
C1B	0.2238 (2)	0.19204 (5)	−0.2535 (3)	0.0182 (3)
H1EB	0.0672	0.1789	−0.2804	0.022*
H1AB	0.2484	0.2130	−0.4077	0.022*
C2B	0.2431 (2)	0.22175 (5)	0.0007 (3)	0.0161 (3)
H2AB	0.1904	0.2024	0.1515	0.019*
C3B	0.4897 (2)	0.23656 (5)	0.0671 (3)	0.0175 (3)
H3AB	0.5469	0.2539	−0.0888	0.021*
C4B	0.6351 (2)	0.19207 (5)	0.1281 (3)	0.0186 (3)
H4EB	0.7983	0.2012	0.1355	0.022*
H4AB	0.6038	0.1798	0.3068	0.022*
C5B	0.5925 (2)	0.15246 (5)	−0.0748 (3)	0.0177 (3)
C6B	0.7499 (3)	0.11531 (6)	−0.0879 (3)	0.0221 (3)
H6B	0.8846	0.1156	0.0301	0.026*
C7B	0.7146 (3)	0.07815 (6)	−0.2680 (3)	0.0236 (3)
H7B	0.8255	0.0536	−0.2757	0.028*
C8B	0.5157 (3)	0.07698 (6)	−0.4379 (3)	0.0222 (3)
H8B	0.4895	0.0515	−0.5614	0.027*
C9B	0.3559 (3)	0.11320 (6)	−0.4265 (3)	0.0203 (3)
H9B	0.2195	0.1121	−0.5415	0.024*
C10B	0.3927 (2)	0.15139 (5)	−0.2476 (3)	0.0177 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0186 (5)	0.0184 (5)	0.0158 (5)	0.0019 (4)	0.0004 (4)	−0.0009 (4)
O2A	0.0229 (5)	0.0232 (5)	0.0231 (6)	0.0013 (4)	0.0107 (4)	0.0005 (4)
C1A	0.0170 (7)	0.0197 (7)	0.0156 (7)	−0.0010 (5)	0.0026 (5)	−0.0003 (6)
C2A	0.0173 (7)	0.0162 (7)	0.0145 (7)	0.0021 (5)	0.0004 (5)	−0.0001 (5)
C3A	0.0160 (7)	0.0223 (8)	0.0157 (7)	0.0006 (5)	0.0031 (5)	0.0003 (5)
C4A	0.0162 (7)	0.0208 (7)	0.0171 (7)	−0.0025 (5)	0.0015 (5)	0.0013 (6)
C5A	0.0172 (7)	0.0224 (7)	0.0133 (7)	0.0011 (5)	−0.0025 (5)	0.0012 (5)
C6A	0.0228 (7)	0.0199 (7)	0.0220 (8)	−0.0014 (6)	−0.0022 (6)	0.0019 (6)
C7A	0.0275 (8)	0.0190 (7)	0.0206 (8)	0.0016 (6)	−0.0024 (6)	−0.0019 (6)
C8A	0.0216 (7)	0.0238 (8)	0.0185 (7)	0.0049 (6)	0.0010 (6)	−0.0030 (6)
C9A	0.0189 (7)	0.0238 (8)	0.0145 (7)	0.0000 (6)	0.0005 (5)	−0.0006 (6)
C10A	0.0165 (7)	0.0199 (7)	0.0132 (7)	0.0021 (5)	−0.0014 (5)	0.0001 (5)
O1B	0.0212 (5)	0.0217 (5)	0.0166 (5)	0.0059 (4)	−0.0002 (4)	−0.0021 (4)
O2B	0.0165 (5)	0.0235 (6)	0.0209 (6)	−0.0003 (4)	0.0000 (4)	−0.0068 (4)
C1B	0.0192 (7)	0.0201 (7)	0.0151 (7)	−0.0002 (6)	0.0005 (5)	−0.0010 (6)
C2B	0.0165 (7)	0.0178 (7)	0.0142 (7)	0.0002 (5)	0.0014 (5)	−0.0006 (6)
C3B	0.0168 (7)	0.0197 (7)	0.0161 (8)	−0.0008 (5)	0.0026 (5)	−0.0024 (5)
C4B	0.0152 (6)	0.0229 (7)	0.0173 (7)	−0.0003 (6)	−0.0004 (5)	−0.0025 (6)
C5B	0.0168 (7)	0.0214 (7)	0.0153 (8)	−0.0020 (6)	0.0041 (5)	0.0008 (5)
C6B	0.0201 (8)	0.0233 (7)	0.0225 (8)	−0.0006 (6)	−0.0003 (6)	−0.0006 (6)
C7B	0.0256 (8)	0.0207 (7)	0.0252 (8)	0.0036 (6)	0.0053 (6)	−0.0010 (6)
C8B	0.0295 (8)	0.0184 (7)	0.0188 (8)	−0.0016 (6)	0.0026 (6)	−0.0031 (6)
C9B	0.0219 (7)	0.0208 (7)	0.0180 (7)	−0.0029 (6)	0.0001 (6)	0.0002 (6)
C10B	0.0190 (7)	0.0190 (7)	0.0153 (7)	−0.0026 (6)	0.0033 (5)	0.0011 (5)

Geometric parameters (Å, º)

O1A—C2A	1.4464 (17)	O1B—C2B	1.4273 (17)
O1A—H01A	0.8400	O1B—H01B	0.8400
O2A—C3A	1.4223 (18)	O2B—C3B	1.4311 (18)
O2A—H02A	0.8400	O2B—H02B	0.8400
C1A—C10A	1.511 (2)	C1B—C10B	1.509 (2)
C1A—C2A	1.522 (2)	C1B—C2B	1.518 (2)
C1A—H1EA	0.9900	C1B—H1EB	0.9900
C1A—1AA	0.9900	C1B—H1AB	0.9900
C2A—C3A	1.5193 (19)	C2B—C3B	1.5183 (19)
C2A—H2AA	1.0000	C2B—H2AB	1.0000
C3A—C4A	1.520 (2)	C3B—C4B	1.528 (2)
C3A—H3AA	1.0000	C3B—H3AB	1.0000
C4A—C5A	1.516 (2)	C4B—C5B	1.512 (2)
C4A—H4EA	0.9900	C4B—H4EB	0.9900
C4A—H4AA	0.9900	C4B—H4AB	0.9900
C5A—C6A	1.398 (2)	C5B—C6B	1.397 (2)
C5A—C10A	1.399 (2)	C5B—C10B	1.403 (2)
C6A—C7A	1.384 (2)	C6B—C7B	1.382 (2)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.392 (2)	C7B—C8B	1.391 (2)
C7A—H7A	0.9500	C7B—H7B	0.9500
C8A—C9A	1.385 (2)	C8B—C9B	1.386 (2)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.402 (2)	C9B—C10B	1.401 (2)
C9A—H9A	0.9500	C9B—H9B	0.9500
C2A—O1A—H01A	109.5	C2B—O1B—H01B	109.5
C3A—O2A—H02A	109.5	C3B—O2B—H02B	109.5
C10A—C1A—C2A	112.99 (12)	C10B—C1B—C2B	113.03 (12)
C10A—C1A—H1EA	109.0	C10B—C1B—H1EB	109.0
C2A—C1A—H1EA	109.0	C2B—C1B—H1EB	109.0
C10A—C1A—1AA	109.0	C10B—C1B—H1AB	109.0
C2A—C1A—1AA	109.0	C2B—C1B—H1AB	109.0
H1EA—C1A—1AA	107.8	H1EB—C1B—H1AB	107.8
O1A—C2A—C3A	111.44 (11)	O1B—C2B—C1B	107.07 (11)
O1A—C2A—C1A	110.34 (11)	O1B—C2B—C3B	112.02 (11)
C3A—C2A—C1A	110.47 (12)	C1B—C2B—C3B	109.92 (11)
O1A—C2A—H2AA	108.2	O1B—C2B—H2AB	109.3
C3A—C2A—H2AA	108.2	C1B—C2B—H2AB	109.3
C1A—C2A—H2AA	108.2	C3B—C2B—H2AB	109.3
O2A—C3A—C2A	111.57 (12)	O2B—C3B—C2B	108.13 (11)
O2A—C3A—C4A	107.52 (12)	O2B—C3B—C4B	110.82 (12)
C2A—C3A—C4A	109.70 (11)	C2B—C3B—C4B	109.28 (12)
O2A—C3A—H3AA	109.3	O2B—C3B—H3AB	109.5
C2A—C3A—H3AA	109.3	C2B—C3B—H3AB	109.5
C4A—C3A—H3AA	109.3	C4B—C3B—H3AB	109.5
C5A—C4A—C3A	113.72 (12)	C5B—C4B—C3B	113.76 (12)
C5A—C4A—H4EA	108.8	C5B—C4B—H4EB	108.8
C3A—C4A—H4EA	108.8	C3B—C4B—H4EB	108.8
C5A—C4A—H4AA	108.8	C5B—C4B—H4AB	108.8
C3A—C4A—H4AA	108.8	C3B—C4B—H4AB	108.8
H4EA—C4A—H4AA	107.7	H4EB—C4B—H4AB	107.7
C6A—C5A—C10A	118.80 (14)	C6B—C5B—C10B	118.67 (14)
C6A—C5A—C4A	120.18 (13)	C6B—C5B—C4B	120.17 (13)
C10A—C5A—C4A	120.99 (13)	C10B—C5B—C4B	121.13 (13)
C7A—C6A—C5A	121.22 (14)	C7B—C6B—C5B	121.70 (14)
C7A—C6A—H6A	119.4	C7B—C6B—H6B	119.1
C5A—C6A—H6A	119.4	C5B—C6B—H6B	119.1
C6A—C7A—C8A	119.84 (14)	C6B—C7B—C8B	119.53 (14)
C6A—C7A—H7A	120.1	C6B—C7B—H7B	120.2
C8A—C7A—H7A	120.1	C8B—C7B—H7B	120.2
C9A—C8A—C7A	119.75 (14)	C9B—C8B—C7B	119.78 (14)
C9A—C8A—H8A	120.1	C9B—C8B—H8B	120.1
C7A—C8A—H8A	120.1	C7B—C8B—H8B	120.1
C8A—C9A—C10A	120.67 (14)	C8B—C9B—C10B	120.91 (14)
C8A—C9A—H9A	119.7	C8B—C9B—H9B	119.5
C10A—C9A—H9A	119.7	C10B—C9B—H9B	119.5
C5A—C10A—C9A	119.72 (13)	C9B—C10B—C5B	119.39 (14)
C5A—C10A—C1A	121.26 (13)	C9B—C10B—C1B	119.67 (13)
C9A—C10A—C1A	118.94 (13)	C5B—C10B—C1B	120.85 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H01A···O1B^i	0.84	1.96	2.7992 (15)	174
O2A—H02A···O2B	0.84	2.03	2.8549 (15)	166
O1B—H01B···O1A	0.84	2.03	2.8645 (15)	171
O2B—H02B···O1A^ii	0.84	1.97	2.7980 (14)	166
C9A—H9A···O2A^iii	0.95	2.45	3.3843 (18)	168

Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x−1, y, z+1.

(k99104) 1,2,3,4-tetrahydro-(S,S)-2,3-naphthalenediol

Crystal data

C10H12O2	F(000) = 352
Mr = 164.20	Dx = 1.324 Mg m^−3
Monoclinic, P21	Melting point: 425 K
a = 5.877 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 28.029 (4) Å	µ = 0.09 mm^−1
c = 5.015 (1) Å	T = 110 K
β = 94.51 (1)°	Block, colorless
V = 823.5 (2) Å^3	0.30 × 0.20 × 0.05 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	1462 independent reflections
Radiation source: fine-focus sealed tube	1258 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 1.5°
ϕ and ω scans with 1.0° steps	h = −6→6
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −33→33
Tmin = 0.97, Tmax = 1.00	l = −5→5
2839 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.033P)^2 + 0.0P] where P = (Fo^2 + 2Fc^2)/3
1462 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.17 e Å^−3
1 restraint	Δρmin = −0.19 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 30 s. The number of scan sets measured was 4; the total number of frames measured was 463.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	−0.0558 (3)	0.29672 (6)	0.4475 (3)	0.0185 (4)
H01A	−0.0090	0.2844	0.5944	0.028*
O2A	0.2850 (3)	0.35946 (7)	0.2762 (3)	0.0246 (5)
H02A	0.3399	0.3319	0.2984	0.037*
C1A	−0.1992 (4)	0.36014 (10)	0.7235 (5)	0.0184 (6)
H1EA	−0.3592	0.3491	0.6934	0.022*
1AA	−0.1275	0.3426	0.8795	0.022*
C2A	−0.0735 (4)	0.34816 (9)	0.4788 (5)	0.0173 (6)
H2AA	−0.1637	0.3612	0.3177	0.021*
C3A	0.1588 (4)	0.37159 (10)	0.4980 (5)	0.0185 (6)
H3AA	0.2463	0.3613	0.6674	0.022*
C4A	0.1317 (4)	0.42535 (10)	0.4988 (5)	0.0193 (6)
H4EA	0.2828	0.4401	0.5450	0.023*
H4AA	0.0784	0.4360	0.3161	0.023*
C5A	−0.0340 (4)	0.44319 (9)	0.6926 (5)	0.0174 (6)
C6A	−0.0312 (5)	0.49076 (10)	0.7722 (5)	0.0215 (6)
H6A	0.0808	0.5117	0.7109	0.026*
C7A	−0.1889 (4)	0.50823 (11)	0.9396 (5)	0.0239 (7)
H7A	−0.1845	0.5408	0.9921	0.029*
C8A	−0.3533 (5)	0.47794 (10)	1.0300 (5)	0.0230 (7)
H8A	−0.4628	0.4899	1.1427	0.028*
C9A	−0.3576 (4)	0.43047 (9)	0.9561 (5)	0.0196 (7)
H9A	−0.4693	0.4098	1.0200	0.024*
C10A	−0.1982 (4)	0.41255 (10)	0.7870 (5)	0.0166 (6)
O1B	0.0964 (3)	0.26193 (6)	−0.0456 (3)	0.0214 (5)
H01B	0.0756	0.2751	0.1011	0.032*
O2B	0.4973 (3)	0.26763 (6)	0.2933 (3)	0.0212 (5)
H02B	0.6337	0.2739	0.3432	0.032*
C1B	0.2245 (4)	0.19222 (9)	−0.2528 (5)	0.0182 (6)
H1EB	0.0678	0.1792	−0.2793	0.022*
H1AB	0.2493	0.2130	−0.4074	0.022*
C2B	0.2440 (4)	0.22202 (9)	−0.0002 (5)	0.0163 (6)
H2AB	0.1911	0.2027	0.1506	0.020*
C3B	0.4900 (4)	0.23649 (9)	0.0667 (5)	0.0178 (6)
H3AB	0.5478	0.2537	−0.0889	0.021*
C4B	0.6349 (4)	0.19201 (9)	0.1281 (5)	0.0185 (6)
H4EB	0.7981	0.2010	0.1355	0.022*
H4AB	0.6033	0.1798	0.3067	0.022*
C5B	0.5916 (4)	0.15266 (9)	−0.0744 (5)	0.0176 (6)
C6B	0.7493 (5)	0.11548 (10)	−0.0879 (5)	0.0222 (7)
H6B	0.8842	0.1159	0.0296	0.027*
C7B	0.7145 (5)	0.07830 (10)	−0.2668 (5)	0.0253 (7)
H7B	0.8252	0.0537	−0.2740	0.030*
C8B	0.5153 (5)	0.07716 (10)	−0.4371 (5)	0.0232 (7)
H8B	0.4889	0.0517	−0.5605	0.028*
C9B	0.3566 (5)	0.11327 (10)	−0.4254 (5)	0.0210 (7)
H9B	0.2203	0.1122	−0.5405	0.025*
C10B	0.3928 (4)	0.15141 (9)	−0.2470 (5)	0.0177 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0207 (11)	0.0185 (11)	0.0162 (9)	0.0016 (9)	0.0006 (8)	−0.0012 (8)
O2A	0.0260 (11)	0.0247 (11)	0.0249 (10)	0.0022 (9)	0.0136 (8)	−0.0003 (9)
C1A	0.0167 (15)	0.0213 (15)	0.0176 (14)	−0.0005 (12)	0.0039 (11)	0.0004 (13)
C2A	0.0196 (15)	0.0139 (15)	0.0183 (14)	0.0032 (12)	0.0005 (11)	0.0005 (12)
C3A	0.0170 (15)	0.0230 (16)	0.0161 (13)	0.0017 (12)	0.0051 (11)	0.0003 (11)
C4A	0.0191 (15)	0.0204 (17)	0.0181 (14)	−0.0009 (13)	0.0000 (12)	0.0029 (12)
C5A	0.0191 (15)	0.0176 (16)	0.0148 (13)	−0.0003 (12)	−0.0035 (11)	0.0018 (12)
C6A	0.0243 (16)	0.0179 (15)	0.0216 (15)	−0.0002 (13)	−0.0016 (12)	0.0011 (13)
C7A	0.0301 (17)	0.0190 (16)	0.0221 (15)	0.0035 (14)	−0.0013 (13)	−0.0020 (13)
C8A	0.0220 (16)	0.0246 (18)	0.0224 (14)	0.0064 (13)	0.0025 (12)	−0.0037 (13)
C9A	0.0167 (16)	0.0233 (17)	0.0190 (14)	−0.0001 (13)	0.0018 (11)	−0.0003 (12)
C10A	0.0170 (15)	0.0173 (15)	0.0149 (14)	0.0024 (13)	−0.0029 (11)	−0.0014 (12)
O1B	0.0236 (10)	0.0217 (11)	0.0185 (10)	0.0073 (9)	−0.0002 (8)	−0.0030 (9)
O2B	0.0177 (10)	0.0244 (12)	0.0213 (11)	0.0004 (9)	0.0001 (8)	−0.0081 (9)
C1B	0.0179 (15)	0.0230 (17)	0.0133 (14)	−0.0010 (13)	−0.0008 (11)	0.0003 (12)
C2B	0.0178 (14)	0.0168 (15)	0.0144 (14)	0.0022 (13)	0.0023 (11)	0.0019 (12)
C3B	0.0201 (14)	0.0191 (15)	0.0144 (14)	0.0020 (13)	0.0034 (11)	−0.0044 (12)
C4B	0.0149 (14)	0.0212 (16)	0.0194 (15)	0.0002 (13)	0.0015 (11)	−0.0020 (12)
C5B	0.0171 (15)	0.0201 (16)	0.0161 (15)	−0.0017 (13)	0.0048 (11)	0.0023 (11)
C6B	0.0182 (16)	0.0252 (16)	0.0230 (15)	−0.0002 (14)	0.0012 (12)	0.0003 (13)
C7B	0.0286 (18)	0.0199 (16)	0.0281 (17)	0.0021 (14)	0.0075 (13)	−0.0031 (14)
C8B	0.0310 (17)	0.0174 (15)	0.0215 (16)	−0.0030 (14)	0.0038 (13)	−0.0028 (13)
C9B	0.0268 (17)	0.0189 (16)	0.0169 (15)	−0.0055 (14)	−0.0005 (12)	0.0021 (14)
C10B	0.0211 (16)	0.0172 (15)	0.0155 (14)	−0.0045 (13)	0.0054 (11)	0.0032 (12)

Geometric parameters (Å, º)

O1A—C2A	1.455 (3)	O1B—C2B	1.423 (3)
O1A—H01A	0.8400	O1B—H01B	0.8400
O2A—C3A	1.426 (3)	O2B—C3B	1.431 (3)
O2A—H02A	0.8400	O2B—H02B	0.8400
C1A—C10A	1.503 (4)	C1B—C10B	1.511 (4)
C1A—C2A	1.519 (3)	C1B—C2B	1.514 (3)
C1A—H1EA	0.9900	C1B—H1EB	0.9900
C1A—1AA	0.9900	C1B—H1AB	0.9900
C2A—C3A	1.511 (3)	C2B—C3B	1.514 (3)
C2A—H2AA	1.0000	C2B—H2AB	1.0000
C3A—C4A	1.515 (4)	C3B—C4B	1.527 (4)
C3A—H3AA	1.0000	C3B—H3AB	1.0000
C4A—C5A	1.514 (3)	C4B—C5B	1.507 (3)
C4A—H4EA	0.9900	C4B—H4EB	0.9900
C4A—H4AA	0.9900	C4B—H4AB	0.9900
C5A—C6A	1.391 (4)	C5B—C6B	1.400 (4)
C5A—C10A	1.401 (4)	C5B—C10B	1.399 (4)
C6A—C7A	1.388 (4)	C6B—C7B	1.380 (4)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.389 (4)	C7B—C8B	1.394 (4)
C7A—H7A	0.9500	C7B—H7B	0.9500
C8A—C9A	1.381 (4)	C8B—C9B	1.381 (4)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.405 (4)	C9B—C10B	1.400 (4)
C9A—H9A	0.9500	C9B—H9B	0.9500
C2A—O1A—H01A	109.5	C2B—O1B—H01B	109.5
C3A—O2A—H02A	109.5	C3B—O2B—H02B	109.5
C10A—C1A—C2A	113.2 (2)	C10B—C1B—C2B	113.3 (2)
C10A—C1A—H1EA	108.9	C10B—C1B—H1EB	108.9
C2A—C1A—H1EA	108.9	C2B—C1B—H1EB	108.9
C10A—C1A—1AA	108.9	C10B—C1B—H1AB	108.9
C2A—C1A—1AA	108.9	C2B—C1B—H1AB	108.9
H1EA—C1A—1AA	107.8	H1EB—C1B—H1AB	107.7
O1A—C2A—C3A	111.4 (2)	O1B—C2B—C3B	112.6 (2)
O1A—C2A—C1A	110.5 (2)	O1B—C2B—C1B	107.16 (19)
C3A—C2A—C1A	110.3 (2)	C3B—C2B—C1B	109.97 (19)
O1A—C2A—H2AA	108.2	O1B—C2B—H2AB	109.0
C3A—C2A—H2AA	108.2	C3B—C2B—H2AB	109.0
C1A—C2A—H2AA	108.2	C1B—C2B—H2AB	109.0
O2A—C3A—C2A	111.7 (2)	O2B—C3B—C2B	107.94 (19)
O2A—C3A—C4A	107.5 (2)	O2B—C3B—C4B	110.89 (19)
C2A—C3A—C4A	109.7 (2)	C2B—C3B—C4B	109.5 (2)
O2A—C3A—H3AA	109.3	O2B—C3B—H3AB	109.5
C2A—C3A—H3AA	109.3	C2B—C3B—H3AB	109.5
C4A—C3A—H3AA	109.3	C4B—C3B—H3AB	109.5
C5A—C4A—C3A	113.8 (2)	C5B—C4B—C3B	113.6 (2)
C5A—C4A—H4EA	108.8	C5B—C4B—H4EB	108.9
C3A—C4A—H4EA	108.8	C3B—C4B—H4EB	108.9
C5A—C4A—H4AA	108.8	C5B—C4B—H4AB	108.9
C3A—C4A—H4AA	108.8	C3B—C4B—H4AB	108.9
H4EA—C4A—H4AA	107.7	H4EB—C4B—H4AB	107.7
C6A—C5A—C10A	118.9 (2)	C6B—C5B—C10B	118.4 (2)
C6A—C5A—C4A	120.4 (2)	C6B—C5B—C4B	120.0 (2)
C10A—C5A—C4A	120.6 (2)	C10B—C5B—C4B	121.6 (2)
C7A—C6A—C5A	121.2 (3)	C7B—C6B—C5B	121.9 (2)
C7A—C6A—H6A	119.4	C7B—C6B—H6B	119.0
C5A—C6A—H6A	119.4	C5B—C6B—H6B	119.0
C6A—C7A—C8A	119.8 (3)	C6B—C7B—C8B	119.3 (3)
C6A—C7A—H7A	120.1	C6B—C7B—H7B	120.3
C8A—C7A—H7A	120.1	C8B—C7B—H7B	120.3
C9A—C8A—C7A	120.0 (3)	C9B—C8B—C7B	119.7 (3)
C9A—C8A—H8A	120.0	C9B—C8B—H8B	120.2
C7A—C8A—H8A	120.0	C7B—C8B—H8B	120.2
C8A—C9A—C10A	120.5 (3)	C8B—C9B—C10B	121.2 (2)
C8A—C9A—H9A	119.8	C8B—C9B—H9B	119.4
C10A—C9A—H9A	119.8	C10B—C9B—H9B	119.4
C5A—C10A—C9A	119.6 (3)	C9B—C10B—C5B	119.5 (2)
C5A—C10A—C1A	121.2 (2)	C9B—C10B—C1B	120.0 (2)
C9A—C10A—C1A	119.1 (2)	C5B—C10B—C1B	120.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H01A···O1B^i	0.84	1.97	2.803 (2)	174
O2A—H02A···O2B	0.84	2.03	2.859 (3)	170
O1B—H01B···O1A	0.84	2.05	2.866 (2)	164
O2B—H02B···O1A^ii	0.84	1.97	2.801 (2)	173
C9A—H9A···O2A^iii	0.95	2.45	3.388 (3)	168

Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x−1, y, z+1.

(k99103) 1,2,3,4-tetrahydro-(S,S)-2,3-naphthalenediol

Crystal data

C10H12O2	F(000) = 352
Mr = 164.20	Dx = 1.315 Mg m^−3
Monoclinic, P21	Melting point: 425 K
a = 5.886 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 28.108 (4) Å	µ = 0.09 mm^−1
c = 5.029 (1) Å	T = 173 K
β = 94.35 (1)°	Block, colorless
V = 829.6 (2) Å^3	0.30 × 0.20 × 0.05 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	1471 independent reflections
Radiation source: fine-focus sealed tube	1223 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 3.5°
ϕ and ω scans with 1.0° steps	h = −6→6
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −28→33
Tmin = 0.97, Tmax = 1.00	l = −5→5
4563 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.0P] where P = (Fo^2 + 2Fc^2)/3
1471 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.15 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 30 s. The number of scan sets measured was 5; the total number of frames measured was 437.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	−0.0557 (3)	0.29689 (7)	0.4468 (3)	0.0255 (5)
H01A	−0.0024	0.2848	0.5910	0.038*
O2A	0.2849 (4)	0.35920 (8)	0.2743 (4)	0.0352 (6)
H02A	0.3350	0.3313	0.2930	0.053*
C1A	−0.1993 (5)	0.35999 (11)	0.7200 (5)	0.0247 (7)
H1EA	−0.3592	0.3492	0.6882	0.030*
1AA	−0.1297	0.3423	0.8757	0.030*
C2A	−0.0718 (5)	0.34813 (10)	0.4775 (5)	0.0228 (7)
H2AA	−0.1609	0.3611	0.3164	0.027*
C3A	0.1591 (5)	0.37136 (11)	0.4971 (5)	0.0245 (7)
H3AA	0.2462	0.3612	0.6660	0.029*
C4A	0.1318 (5)	0.42491 (11)	0.4963 (5)	0.0261 (7)
H4EA	0.2823	0.4397	0.5426	0.031*
H4AA	0.0792	0.4354	0.3140	0.031*
C5A	−0.0351 (5)	0.44263 (11)	0.6895 (5)	0.0248 (7)
C6A	−0.0309 (5)	0.49021 (11)	0.7682 (6)	0.0316 (8)
H6A	0.0815	0.5109	0.7071	0.038*
C7A	−0.1887 (5)	0.50762 (12)	0.9343 (5)	0.0332 (8)
H7A	−0.1845	0.5402	0.9857	0.040*
C8A	−0.3523 (6)	0.47770 (12)	1.0256 (6)	0.0341 (8)
H8A	−0.4617	0.4897	1.1379	0.041*
C9A	−0.3558 (5)	0.43031 (11)	0.9526 (5)	0.0285 (8)
H9A	−0.4669	0.4097	1.0174	0.034*
C10A	−0.1975 (5)	0.41232 (11)	0.7843 (5)	0.0224 (7)
O1B	0.0990 (3)	0.26219 (7)	−0.0478 (4)	0.0313 (5)
H01B	0.0798	0.2757	0.0979	0.047*
O2B	0.4981 (3)	0.26787 (7)	0.2903 (4)	0.0300 (5)
H02B	0.6341	0.2749	0.3364	0.045*
C1B	0.2267 (5)	0.19234 (11)	−0.2520 (5)	0.0277 (7)
H1EB	0.0700	0.1794	−0.2781	0.033*
H1AB	0.2521	0.2129	−0.4066	0.033*
C2B	0.2461 (5)	0.22217 (10)	−0.0014 (5)	0.0229 (7)
H2AB	0.1926	0.2030	0.1494	0.028*
C3B	0.4909 (5)	0.23657 (11)	0.0653 (5)	0.0251 (7)
H3AB	0.5494	0.2536	−0.0903	0.030*
C4B	0.6343 (5)	0.19231 (11)	0.1276 (5)	0.0276 (7)
H4EB	0.7974	0.2012	0.1352	0.033*
H4AB	0.6019	0.1803	0.3060	0.033*
C5B	0.5920 (5)	0.15278 (11)	−0.0730 (5)	0.0241 (7)
C6B	0.7487 (5)	0.11552 (12)	−0.0852 (6)	0.0326 (8)
H6B	0.8830	0.1157	0.0322	0.039*
C7B	0.7128 (6)	0.07863 (12)	−0.2633 (6)	0.0368 (8)
H7B	0.8230	0.0541	−0.2707	0.044*
C8B	0.5153 (6)	0.07742 (12)	−0.4321 (6)	0.0350 (8)
H8B	0.4886	0.0518	−0.5540	0.042*
C9B	0.3579 (5)	0.11358 (11)	−0.4217 (5)	0.0305 (8)
H9B	0.2224	0.1126	−0.5369	0.037*
C10B	0.3936 (5)	0.15165 (10)	−0.2454 (5)	0.0232 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0277 (12)	0.0238 (12)	0.0247 (10)	0.0042 (10)	0.0006 (9)	−0.0036 (9)
O2A	0.0361 (14)	0.0358 (14)	0.0361 (12)	0.0015 (11)	0.0186 (10)	−0.0007 (10)
C1A	0.0247 (17)	0.0256 (18)	0.0243 (14)	−0.0019 (14)	0.0043 (12)	0.0003 (13)
C2A	0.0261 (17)	0.0209 (17)	0.0208 (15)	0.0037 (14)	−0.0006 (12)	0.0001 (12)
C3A	0.0223 (17)	0.0308 (19)	0.0212 (14)	−0.0002 (14)	0.0064 (11)	−0.0004 (12)
C4A	0.0226 (17)	0.030 (2)	0.0260 (15)	−0.0037 (15)	0.0037 (13)	0.0010 (13)
C5A	0.0245 (17)	0.0287 (19)	0.0204 (13)	0.0024 (15)	−0.0033 (12)	−0.0009 (13)
C6A	0.037 (2)	0.0257 (19)	0.0321 (17)	−0.0020 (16)	0.0005 (15)	0.0042 (14)
C7A	0.041 (2)	0.0240 (19)	0.0337 (18)	0.0042 (17)	−0.0014 (15)	−0.0036 (14)
C8A	0.036 (2)	0.036 (2)	0.0309 (16)	0.0083 (17)	0.0056 (14)	−0.0081 (15)
C9A	0.0265 (19)	0.033 (2)	0.0256 (16)	0.0022 (15)	0.0023 (14)	−0.0020 (14)
C10A	0.0197 (16)	0.0270 (18)	0.0200 (14)	−0.0001 (14)	−0.0025 (12)	−0.0004 (12)
O1B	0.0332 (12)	0.0343 (13)	0.0255 (11)	0.0104 (11)	−0.0028 (9)	−0.0047 (10)
O2B	0.0248 (11)	0.0314 (13)	0.0334 (12)	0.0002 (11)	−0.0007 (9)	−0.0108 (9)
C1B	0.0295 (18)	0.031 (2)	0.0220 (15)	0.0006 (15)	−0.0014 (12)	−0.0010 (13)
C2B	0.0210 (16)	0.0261 (19)	0.0218 (15)	0.0027 (15)	0.0026 (12)	0.0023 (13)
C3B	0.0260 (17)	0.0283 (18)	0.0215 (15)	−0.0018 (14)	0.0058 (12)	−0.0065 (13)
C4B	0.0213 (17)	0.032 (2)	0.0297 (16)	−0.0002 (15)	0.0008 (12)	−0.0034 (14)
C5B	0.0232 (17)	0.0276 (18)	0.0225 (15)	−0.0019 (15)	0.0074 (12)	0.0013 (12)
C6B	0.030 (2)	0.033 (2)	0.0344 (17)	0.0031 (17)	0.0029 (14)	−0.0035 (15)
C7B	0.042 (2)	0.030 (2)	0.0389 (19)	0.0053 (17)	0.0084 (15)	−0.0031 (16)
C8B	0.049 (2)	0.0257 (19)	0.0310 (18)	−0.0018 (17)	0.0046 (15)	−0.0030 (15)
C9B	0.035 (2)	0.030 (2)	0.0261 (16)	−0.0051 (17)	0.0009 (13)	−0.0005 (15)
C10B	0.0248 (17)	0.0235 (18)	0.0218 (15)	−0.0013 (15)	0.0047 (12)	0.0036 (12)

Geometric parameters (Å, º)

O1A—C2A	1.452 (3)	O1B—C2B	1.428 (3)
O1A—H01A	0.8400	O1B—H01B	0.8400
O2A—C3A	1.431 (3)	O2B—C3B	1.432 (3)
O2A—H02A	0.8400	O2B—H02B	0.8400
C1A—C10A	1.506 (4)	C1B—C10B	1.507 (4)
C1A—C2A	1.517 (4)	C1B—C2B	1.511 (4)
C1A—H1EA	0.9900	C1B—H1EB	0.9900
C1A—1AA	0.9900	C1B—H1AB	0.9900
C2A—C3A	1.504 (4)	C2B—C3B	1.510 (4)
C2A—H2AA	1.0000	C2B—H2AB	1.0000
C3A—C4A	1.514 (4)	C3B—C4B	1.523 (4)
C3A—H3AA	1.0000	C3B—H3AB	1.0000
C4A—C5A	1.517 (4)	C4B—C5B	1.509 (4)
C4A—H4EA	0.9900	C4B—H4EB	0.9900
C4A—H4AA	0.9900	C4B—H4AB	0.9900
C5A—C6A	1.394 (4)	C5B—C6B	1.400 (4)
C5A—C10A	1.391 (4)	C5B—C10B	1.401 (4)
C6A—C7A	1.385 (4)	C6B—C7B	1.376 (4)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.383 (4)	C7B—C8B	1.387 (4)
C7A—H7A	0.9500	C7B—H7B	0.9500
C8A—C9A	1.381 (4)	C8B—C9B	1.379 (4)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.400 (4)	C9B—C10B	1.395 (4)
C9A—H9A	0.9500	C9B—H9B	0.9500
C2A—O1A—H01A	109.5	C2B—O1B—H01B	109.5
C3A—O2A—H02A	109.5	C3B—O2B—H02B	109.5
C10A—C1A—C2A	113.0 (2)	C10B—C1B—C2B	113.3 (2)
C10A—C1A—H1EA	109.0	C10B—C1B—H1EB	108.9
C2A—C1A—H1EA	109.0	C2B—C1B—H1EB	108.9
C10A—C1A—1AA	109.0	C10B—C1B—H1AB	108.9
C2A—C1A—1AA	109.0	C2B—C1B—H1AB	108.9
H1EA—C1A—1AA	107.8	H1EB—C1B—H1AB	107.7
O1A—C2A—C3A	111.8 (2)	O1B—C2B—C3B	112.4 (2)
O1A—C2A—C1A	110.1 (2)	O1B—C2B—C1B	107.1 (2)
C3A—C2A—C1A	110.6 (2)	C3B—C2B—C1B	110.1 (2)
O1A—C2A—H2AA	108.1	O1B—C2B—H2AB	109.0
C3A—C2A—H2AA	108.1	C3B—C2B—H2AB	109.0
C1A—C2A—H2AA	108.1	C1B—C2B—H2AB	109.0
O2A—C3A—C2A	111.3 (2)	O2B—C3B—C2B	108.1 (2)
O2A—C3A—C4A	107.2 (2)	O2B—C3B—C4B	110.9 (2)
C2A—C3A—C4A	109.7 (2)	C2B—C3B—C4B	109.4 (2)
O2A—C3A—H3AA	109.5	O2B—C3B—H3AB	109.5
C2A—C3A—H3AA	109.5	C2B—C3B—H3AB	109.5
C4A—C3A—H3AA	109.5	C4B—C3B—H3AB	109.5
C5A—C4A—C3A	113.5 (2)	C5B—C4B—C3B	113.8 (2)
C5A—C4A—H4EA	108.9	C5B—C4B—H4EB	108.8
C3A—C4A—H4EA	108.9	C3B—C4B—H4EB	108.8
C5A—C4A—H4AA	108.9	C5B—C4B—H4AB	108.8
C3A—C4A—H4AA	108.9	C3B—C4B—H4AB	108.8
H4EA—C4A—H4AA	107.7	H4EB—C4B—H4AB	107.7
C6A—C5A—C10A	119.2 (3)	C6B—C5B—C10B	118.5 (3)
C6A—C5A—C4A	119.9 (3)	C6B—C5B—C4B	120.3 (3)
C10A—C5A—C4A	120.9 (3)	C10B—C5B—C4B	121.2 (3)
C7A—C6A—C5A	120.8 (3)	C7B—C6B—C5B	121.5 (3)
C7A—C6A—H6A	119.6	C7B—C6B—H6B	119.2
C5A—C6A—H6A	119.6	C5B—C6B—H6B	119.2
C6A—C7A—C8A	120.1 (3)	C6B—C7B—C8B	119.8 (3)
C6A—C7A—H7A	120.0	C6B—C7B—H7B	120.1
C8A—C7A—H7A	120.0	C8B—C7B—H7B	120.1
C9A—C8A—C7A	119.7 (3)	C9B—C8B—C7B	119.6 (3)
C9A—C8A—H8A	120.2	C9B—C8B—H8B	120.2
C7A—C8A—H8A	120.2	C7B—C8B—H8B	120.2
C8A—C9A—C10A	120.8 (3)	C8B—C9B—C10B	121.3 (3)
C8A—C9A—H9A	119.6	C8B—C9B—H9B	119.3
C10A—C9A—H9A	119.6	C10B—C9B—H9B	119.3
C5A—C10A—C9A	119.5 (3)	C5B—C10B—C9B	119.3 (3)
C5A—C10A—C1A	121.2 (2)	C5B—C10B—C1B	120.5 (3)
C9A—C10A—C1A	119.2 (3)	C9B—C10B—C1B	120.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H01A···O1B^i	0.84	1.97	2.809 (3)	173
O2A—H02A···O2B	0.84	2.03	2.856 (3)	169
O1B—H01B···O1A	0.84	2.07	2.882 (3)	163
O2B—H02B···O1A^ii	0.84	1.97	2.805 (3)	175
C9A—H9A···O2A^iii	0.95	2.47	3.407 (4)	169

Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x−1, y, z+1.

(cis-1,2-CHD) cis-1,2-cyclohexanediol

Crystal data

C6H12O2	F(000) = 512
Mr = 116.16	Dx = 1.207 Mg m^−3
Orthorhombic, Pbca	Melting point = 370–372 K
a = 8.545 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.588 (1) Å	µ = 0.09 mm^−1
c = 19.717 (4) Å	T = 173 K
V = 1278.4 (4) Å^3	Plate. Major faces are {001} and {110}., colorless
Z = 8	0.32 × 0.25 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer	1124 independent reflections
Radiation source: fine-focus sealed tube	915 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 3.2°
ϕ and ω scans with 1.0° steps	h = −10→10
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −9→8
Tmin = 0.98, Tmax = 0.99	l = −23→23
2046 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.037P)^2 + 0.24P] where P = (Fo^2 + 2Fc^2)/3
1124 reflections	(Δ/σ)max < 0.001
75 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 180 s. The number of scan sets measured was 3; the total number of frames measured was 346.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.15954 (12)	0.06166 (13)	0.04206 (5)	0.0275 (3)
H01	0.2230	0.1120	0.0159	0.041*
O2	−0.12982 (12)	0.24476 (13)	0.03210 (5)	0.0279 (4)
H02	−0.1025	0.1542	0.0107	0.042*
C1	0.11073 (18)	0.18253 (18)	0.09370 (8)	0.0233 (4)
H1A	0.2057	0.2415	0.1127	0.028*
C2	0.00471 (17)	0.32274 (18)	0.06384 (8)	0.0239 (4)
H2E	0.0644	0.3921	0.0293	0.029*
C3	−0.05477 (19)	0.44645 (19)	0.11849 (7)	0.0289 (4)
H3E	−0.1302	0.5305	0.0983	0.035*
H3A	0.0340	0.5150	0.1371	0.035*
C4	−0.13409 (19)	0.3458 (2)	0.17567 (8)	0.0325 (5)
H4A	−0.2306	0.2894	0.1583	0.039*
H4E	−0.1644	0.4293	0.2119	0.039*
C5	−0.0266 (2)	0.2051 (2)	0.20510 (8)	0.0364 (5)
H5E	−0.0839	0.1369	0.2400	0.044*
H5A	0.0640	0.2624	0.2273	0.044*
C6	0.03188 (19)	0.0801 (2)	0.14987 (8)	0.0301 (5)
H6E	0.1070	−0.0049	0.1697	0.036*
H6A	−0.0574	0.0127	0.1311	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0256 (7)	0.0249 (6)	0.0319 (7)	0.0001 (5)	0.0068 (5)	−0.0025 (5)
O2	0.0267 (7)	0.0275 (7)	0.0296 (7)	0.0050 (5)	−0.0066 (5)	−0.0068 (5)
C1	0.0205 (9)	0.0232 (8)	0.0261 (9)	0.0003 (7)	−0.0013 (7)	−0.0039 (7)
C2	0.0235 (10)	0.0220 (8)	0.0262 (9)	−0.0028 (7)	−0.0027 (7)	−0.0001 (7)
C3	0.0291 (10)	0.0254 (9)	0.0323 (10)	0.0018 (7)	−0.0042 (8)	−0.0051 (7)
C4	0.0314 (10)	0.0382 (10)	0.0278 (10)	0.0047 (8)	0.0015 (8)	−0.0103 (8)
C5	0.0389 (11)	0.0456 (11)	0.0249 (10)	0.0012 (9)	0.0007 (8)	0.0027 (8)
C6	0.0318 (10)	0.0304 (9)	0.0282 (9)	0.0049 (8)	−0.0002 (7)	0.0067 (7)

Geometric parameters (Å, º)

O1—C1	1.4324 (17)	C3—H3E	0.9900
O1—H01	0.8400	C3—H3A	0.9900
O2—C2	1.4365 (17)	C4—C5	1.524 (2)
O2—H02	0.8400	C4—H4A	0.9900
C1—C6	1.512 (2)	C4—H4E	0.9900
C1—C2	1.516 (2)	C5—C6	1.528 (2)
C1—H1A	1.0000	C5—H5E	0.9900
C2—C3	1.517 (2)	C5—H5A	0.9900
C2—H2E	1.0000	C6—H6E	0.9900
C3—C4	1.521 (2)	C6—H6A	0.9900
C1—O1—H01	109.5	H3E—C3—H3A	108.0
C2—O2—H02	109.5	C3—C4—C5	111.44 (13)
O1—C1—C6	108.74 (11)	C3—C4—H4A	109.3
O1—C1—C2	110.32 (12)	C5—C4—H4A	109.3
C6—C1—C2	112.27 (13)	C3—C4—H4E	109.3
O1—C1—H1A	108.5	C5—C4—H4E	109.3
C6—C1—H1A	108.5	H4A—C4—H4E	108.0
C2—C1—H1A	108.5	C4—C5—C6	111.14 (13)
O2—C2—C1	110.99 (12)	C4—C5—H5E	109.4
O2—C2—C3	107.24 (12)	C6—C5—H5E	109.4
C1—C2—C3	111.01 (12)	C4—C5—H5A	109.4
O2—C2—H2E	109.2	C6—C5—H5A	109.4
C1—C2—H2E	109.2	H5E—C5—H5A	108.0
C3—C2—H2E	109.2	C1—C6—C5	110.40 (13)
C2—C3—C4	111.42 (12)	C1—C6—H6E	109.6
C2—C3—H3E	109.3	C5—C6—H6E	109.6
C4—C3—H3E	109.3	C1—C6—H6A	109.6
C2—C3—H3A	109.3	C5—C6—H6A	109.6
C4—C3—H3A	109.3	H6E—C6—H6A	108.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O2^i	0.84	1.91	2.7451 (14)	171
O2—H02···O1^ii	0.84	2.00	2.7584 (14)	150

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x, −y, −z.

(k99096) cis-1,2-cyclohexanediol

Crystal data

C6H12O2	Dx = 1.182 Mg m^−3
Mr = 116.16	Melting point = 370–372 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 8.617 (1) Å	Cell parameters from 14491 reflections
b = 7.693 (1) Å	θ = 1.0–25.0°
c = 19.695 (3) Å	µ = 0.09 mm^−1
V = 1305.6 (3) Å^3	T = 299 K
Z = 8	Thick plate. Major faces are {001} and {110}., colorless
F(000) = 512	0.40 × 0.32 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer	1133 independent reflections
Radiation source: fine-focus sealed tube	777 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
ϕ and ω scans with 1.5° steps	h = −10→10
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −9→9
Tmin = 0.98, Tmax = 0.99	l = −23→23
2017 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.025P)^2 + 0.15P] where P = (Fo^2 + 2Fc^2)/3
1133 reflections	(Δ/σ)max < 0.001
75 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 60 s. The number of scan sets measured was 3; the total number of frames measured was 273.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.15845 (12)	0.06377 (12)	0.04103 (5)	0.0447 (3)
H01	0.2219	0.1120	0.0164	0.067*
O2	−0.12725 (10)	0.24504 (13)	0.03120 (5)	0.0462 (3)
H02	−0.1003	0.1595	0.0093	0.069*
C1	0.10979 (16)	0.18126 (17)	0.09290 (7)	0.0359 (4)
H1A	0.2020	0.2375	0.1120	0.043*
C2	0.00538 (15)	0.32016 (17)	0.06377 (7)	0.0366 (4)
H2E	0.0639	0.3885	0.0305	0.044*
C3	−0.05429 (18)	0.44011 (19)	0.11881 (7)	0.0466 (5)
H3E	−0.1274	0.5219	0.0992	0.056*
H3A	0.0317	0.5059	0.1376	0.056*
C4	−0.13332 (19)	0.3392 (2)	0.17515 (8)	0.0543 (5)
H4E	−0.1633	0.4186	0.2111	0.065*
H4A	−0.2268	0.2852	0.1576	0.065*
C5	−0.0275 (2)	0.2002 (2)	0.20402 (8)	0.0630 (5)
H5E	−0.0837	0.1330	0.2377	0.076*
H5A	0.0601	0.2549	0.2264	0.076*
C6	0.03130 (19)	0.0794 (2)	0.14826 (8)	0.0501 (5)
H6E	0.1041	−0.0033	0.1675	0.060*
H6A	−0.0551	0.0148	0.1293	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0373 (7)	0.0382 (7)	0.0587 (7)	−0.0006 (5)	0.0092 (5)	−0.0053 (5)
O2	0.0431 (6)	0.0451 (7)	0.0503 (7)	0.0111 (6)	−0.0132 (5)	−0.0120 (5)
C1	0.0310 (8)	0.0348 (9)	0.0419 (9)	−0.0003 (7)	−0.0014 (7)	−0.0034 (7)
C2	0.0379 (9)	0.0309 (8)	0.0410 (9)	−0.0030 (7)	−0.0022 (7)	0.0007 (7)
C3	0.0476 (10)	0.0387 (10)	0.0534 (11)	0.0037 (8)	−0.0059 (8)	−0.0109 (8)
C4	0.0520 (11)	0.0648 (12)	0.0460 (11)	0.0080 (9)	0.0031 (8)	−0.0155 (9)
C5	0.0682 (12)	0.0797 (13)	0.0410 (10)	0.0033 (11)	0.0040 (9)	0.0065 (10)
C6	0.0512 (11)	0.0503 (11)	0.0486 (10)	0.0080 (9)	0.0000 (8)	0.0135 (9)

Geometric parameters (Å, º)

O1—C1	1.4271 (16)	C3—H3E	0.9700
O1—H01	0.8200	C3—H3A	0.9700
O2—C2	1.4323 (15)	C4—C5	1.516 (2)
O2—H02	0.8200	C4—H4E	0.9700
C1—C6	1.5035 (18)	C4—H4A	0.9700
C1—C2	1.5102 (18)	C5—C6	1.526 (2)
C1—H1A	0.9800	C5—H5E	0.9700
C2—C3	1.5135 (18)	C5—H5A	0.9700
C2—H2E	0.9800	C6—H6E	0.9700
C3—C4	1.516 (2)	C6—H6A	0.9700
C1—O1—H01	109.5	H3E—C3—H3A	108.0
C2—O2—H02	109.5	C5—C4—C3	111.46 (13)
O1—C1—C6	108.73 (11)	C5—C4—H4E	109.3
O1—C1—C2	110.56 (11)	C3—C4—H4E	109.3
C6—C1—C2	112.11 (12)	C5—C4—H4A	109.3
O1—C1—H1A	108.5	C3—C4—H4A	109.3
C6—C1—H1A	108.5	H4E—C4—H4A	108.0
C2—C1—H1A	108.5	C4—C5—C6	111.08 (13)
O2—C2—C1	111.10 (11)	C4—C5—H5E	109.4
O2—C2—C3	107.20 (11)	C6—C5—H5E	109.4
C1—C2—C3	111.21 (12)	C4—C5—H5A	109.4
O2—C2—H2E	109.1	C6—C5—H5A	109.4
C1—C2—H2E	109.1	H5E—C5—H5A	108.0
C3—C2—H2E	109.1	C1—C6—C5	110.73 (12)
C2—C3—C4	111.38 (12)	C1—C6—H6E	109.5
C2—C3—H3E	109.4	C5—C6—H6E	109.5
C4—C3—H3E	109.4	C1—C6—H6A	109.5
C2—C3—H3A	109.4	C5—C6—H6A	109.5
C4—C3—H3A	109.4	H6E—C6—H6A	108.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O2^i	0.82	1.94	2.7564 (14)	171
O2—H02···O1^ii	0.82	2.05	2.7821 (14)	149

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x, −y, −z.

(trans-1,2-CHD_1) rac-trans-1,2-cyclohexanediol

Crystal data

C6H12O2	F(000) = 512
Mr = 116.16	Dx = 1.219 Mg m^−3
Orthorhombic, Pbca	Melting point = 376–377 K
a = 8.415 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.799 (1) Å	µ = 0.09 mm^−1
c = 19.295 (2) Å	T = 173 K
V = 1266.3 (3) Å^3	Plate. Largest face is {001}., colorless
Z = 8	0.30 × 0.25 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	1099 independent reflections
Radiation source: fine-focus sealed tube	976 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 18 pixels mm^-1	θmax = 24.9°, θmin = 3.2°
ϕ and ω scans with 2.0° steps	h = −9→9
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −9→9
Tmin = 0.97, Tmax = 0.99	l = −22→22
2001 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 0.34P] where P = (Fo^2 + 2Fc^2)/3
1099 reflections	(Δ/σ)max < 0.001
75 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 60 s. The number of scan sets measured was 3; the total number of frames measured was 210.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.31931 (9)	0.41673 (10)	0.43574 (4)	0.0242 (2)
H01	0.3588	0.4952	0.4601	0.036*
O2	0.59910 (11)	0.28810 (10)	0.49844 (4)	0.0303 (3)
H02	0.6655	0.2231	0.5176	0.045*
C1	0.44268 (13)	0.33382 (14)	0.39711 (6)	0.0214 (3)
H1A	0.5212	0.4218	0.3813	0.026*
C2	0.52748 (14)	0.20101 (14)	0.44099 (6)	0.0215 (3)
H2A	0.4473	0.1176	0.4591	0.026*
C3	0.65007 (14)	0.10399 (16)	0.39847 (6)	0.0280 (3)
H3E	0.7009	0.0153	0.4277	0.034*
H3A	0.7337	0.1843	0.3827	0.034*
C4	0.57303 (17)	0.01905 (17)	0.33560 (6)	0.0329 (3)
H4E	0.6557	−0.0389	0.3076	0.039*
H4A	0.4963	−0.0689	0.3514	0.039*
C5	0.48747 (16)	0.15112 (18)	0.29108 (6)	0.0343 (3)
H5E	0.4326	0.0925	0.2524	0.041*
H5A	0.5660	0.2317	0.2711	0.041*
C6	0.36633 (15)	0.25074 (16)	0.33411 (6)	0.0262 (3)
H6E	0.3171	0.3406	0.3049	0.031*
H6A	0.2812	0.1719	0.3495	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0227 (4)	0.0217 (5)	0.0283 (5)	0.0021 (3)	0.0006 (3)	−0.0045 (3)
O2	0.0361 (6)	0.0254 (5)	0.0295 (5)	0.0070 (4)	−0.0132 (4)	−0.0092 (4)
C1	0.0208 (6)	0.0205 (6)	0.0228 (6)	0.0000 (5)	0.0030 (5)	0.0004 (5)
C2	0.0237 (6)	0.0207 (6)	0.0201 (6)	0.0000 (5)	−0.0030 (5)	−0.0030 (5)
C3	0.0268 (7)	0.0272 (7)	0.0301 (7)	0.0058 (5)	−0.0011 (5)	−0.0047 (5)
C4	0.0380 (8)	0.0334 (7)	0.0272 (7)	0.0074 (6)	0.0013 (6)	−0.0101 (6)
C5	0.0414 (8)	0.0407 (8)	0.0210 (6)	0.0036 (6)	0.0012 (6)	−0.0039 (6)
C6	0.0291 (7)	0.0291 (6)	0.0204 (6)	0.0016 (6)	−0.0023 (5)	0.0017 (5)

Geometric parameters (Å, º)

O1—C1	1.4323 (13)	C3—H3E	0.9900
O1—H01	0.8400	C3—H3A	0.9900
O2—C2	1.4330 (13)	C4—C5	1.5222 (18)
O2—H02	0.8400	C4—H4E	0.9900
C1—C2	1.5163 (16)	C4—H4A	0.9900
C1—C6	1.5200 (16)	C5—C6	1.5270 (17)
C1—H1A	1.0000	C5—H5E	0.9900
C2—C3	1.5199 (16)	C5—H5A	0.9900
C2—H2A	1.0000	C6—H6E	0.9900
C3—C4	1.5266 (17)	C6—H6A	0.9900
C1—O1—H01	109.5	H3E—C3—H3A	108.0
C2—O2—H02	109.5	C5—C4—C3	110.83 (10)
O1—C1—C2	111.03 (9)	C5—C4—H4E	109.5
O1—C1—C6	107.60 (9)	C3—C4—H4E	109.5
C2—C1—C6	110.75 (9)	C5—C4—H4A	109.5
O1—C1—H1A	109.1	C3—C4—H4A	109.5
C2—C1—H1A	109.1	H4E—C4—H4A	108.1
C6—C1—H1A	109.1	C4—C5—C6	110.69 (10)
O2—C2—C1	107.83 (8)	C4—C5—H5E	109.5
O2—C2—C3	111.60 (9)	C6—C5—H5E	109.5
C1—C2—C3	110.98 (9)	C4—C5—H5A	109.5
O2—C2—H2A	108.8	C6—C5—H5A	109.5
C1—C2—H2A	108.8	H5E—C5—H5A	108.1
C3—C2—H2A	108.8	C1—C6—C5	111.69 (10)
C2—C3—C4	110.90 (10)	C1—C6—H6E	109.3
C2—C3—H3E	109.5	C5—C6—H6E	109.3
C4—C3—H3E	109.5	C1—C6—H6A	109.3
C2—C3—H3A	109.5	C5—C6—H6A	109.3
C4—C3—H3A	109.5	H6E—C6—H6A	107.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O2^i	0.84	1.90	2.7173 (11)	163
O2—H02···O1^ii	0.84	1.92	2.7565 (11)	177

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+1/2, −z+1.

(k99093) rac-trans-1,2-cyclohexanediol

Crystal data

C6H12O2	F(000) = 512
Mr = 116.16	Dx = 1.191 Mg m^−3
Orthorhombic, Pbca	Melting point = 376–377 K
a = 8.491 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.893 (1) Å	µ = 0.09 mm^−1
c = 19.331 (2) Å	T = 299 K
V = 1295.6 (3) Å^3	Thick plate. Largest face is {001}., colorless
Z = 8	0.22 × 0.21 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer	1136 independent reflections
Radiation source: fine-focus sealed tube	924 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 3.2°
ϕ and ω scans with 2.0° steps	h = −10→10
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −9→9
Tmin = 0.97, Tmax = 0.99	l = −22→22
2071 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.2P] where P = (Fo^2 + 2Fc^2)/3
1136 reflections	(Δ/σ)max < 0.001
75 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 80 s. The number of scan sets measured was 2; the total number of frames measured was 172.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.32005 (9)	0.41472 (10)	0.43700 (5)	0.0447 (3)
H01	0.3583	0.4894	0.4613	0.067*
O2	0.59992 (12)	0.29040 (11)	0.49777 (5)	0.0556 (3)
H02	0.6629	0.2268	0.5168	0.083*
C1	0.44207 (14)	0.33474 (15)	0.39782 (6)	0.0374 (3)
H1A	0.5169	0.4212	0.3823	0.045*
C2	0.52875 (14)	0.20494 (15)	0.44057 (6)	0.0382 (3)
H2A	0.4522	0.1230	0.4585	0.046*
C3	0.64930 (15)	0.11061 (18)	0.39748 (7)	0.0505 (4)
H3E	0.6996	0.0246	0.4257	0.061*
H3A	0.7299	0.1890	0.3821	0.061*
C4	0.57318 (19)	0.02765 (19)	0.33513 (7)	0.0585 (4)
H4E	0.6536	−0.0269	0.3073	0.070*
H4A	0.4999	−0.0588	0.3505	0.070*
C5	0.48640 (19)	0.1570 (2)	0.29154 (7)	0.0613 (4)
H5E	0.4327	0.1000	0.2538	0.074*
H5A	0.5613	0.2361	0.2718	0.074*
C6	0.36673 (16)	0.25342 (18)	0.33519 (7)	0.0475 (4)
H6E	0.3177	0.3405	0.3071	0.057*
H6A	0.2849	0.1760	0.3503	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0417 (5)	0.0386 (5)	0.0538 (6)	0.0041 (4)	0.0012 (4)	−0.0074 (4)
O2	0.0659 (7)	0.0439 (6)	0.0570 (6)	0.0133 (5)	−0.0230 (5)	−0.0179 (5)
C1	0.0369 (6)	0.0337 (7)	0.0416 (7)	−0.0015 (6)	0.0052 (6)	0.0017 (5)
C2	0.0423 (7)	0.0336 (7)	0.0386 (7)	0.0006 (6)	−0.0044 (6)	−0.0045 (5)
C3	0.0476 (8)	0.0481 (8)	0.0558 (9)	0.0101 (7)	−0.0027 (6)	−0.0099 (7)
C4	0.0663 (9)	0.0594 (9)	0.0497 (8)	0.0134 (8)	0.0012 (7)	−0.0177 (7)
C5	0.0733 (10)	0.0717 (10)	0.0388 (8)	0.0068 (9)	0.0015 (7)	−0.0071 (7)
C6	0.0527 (8)	0.0509 (8)	0.0390 (8)	0.0036 (7)	−0.0047 (6)	0.0038 (6)

Geometric parameters (Å, º)

O1—C1	1.4302 (14)	C3—H3E	0.9700
O1—H01	0.8200	C3—H3A	0.9700
O2—C2	1.4292 (14)	C4—C5	1.515 (2)
O2—H02	0.8200	C4—H4E	0.9700
C1—C2	1.5081 (17)	C4—H4A	0.9700
C1—C6	1.5123 (18)	C5—C6	1.5243 (19)
C1—H1A	0.9800	C5—H5E	0.9700
C2—C3	1.5153 (17)	C5—H5A	0.9700
C2—H2A	0.9800	C6—H6E	0.9700
C3—C4	1.5164 (19)	C6—H6A	0.9700
C1—O1—H01	109.5	H3E—C3—H3A	108.0
C2—O2—H02	109.5	C5—C4—C3	111.00 (12)
O1—C1—C2	111.30 (9)	C5—C4—H4E	109.4
O1—C1—C6	107.75 (9)	C3—C4—H4E	109.4
C2—C1—C6	110.90 (10)	C5—C4—H4A	109.4
O1—C1—H1A	108.9	C3—C4—H4A	109.4
C2—C1—H1A	108.9	H4E—C4—H4A	108.0
C6—C1—H1A	108.9	C4—C5—C6	110.66 (11)
O2—C2—C1	108.04 (9)	C4—C5—H5E	109.5
O2—C2—C3	111.81 (10)	C6—C5—H5E	109.5
C1—C2—C3	111.24 (10)	C4—C5—H5A	109.5
O2—C2—H2A	108.6	C6—C5—H5A	109.5
C1—C2—H2A	108.6	H5E—C5—H5A	108.1
C3—C2—H2A	108.6	C1—C6—C5	111.91 (10)
C2—C3—C4	111.18 (11)	C1—C6—H6E	109.2
C2—C3—H3E	109.4	C5—C6—H6E	109.2
C4—C3—H3E	109.4	C1—C6—H6A	109.2
C2—C3—H3A	109.4	C5—C6—H6A	109.2
C4—C3—H3A	109.4	H6E—C6—H6A	107.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O2^i	0.82	1.94	2.7330 (12)	162
O2—H02···O1^ii	0.82	1.96	2.7758 (13)	177

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+1/2, −z+1.

(trans-1,2-CHD_2) rac-trans-1,2-cyclohexanediol

Crystal data

C6H12O2	F(000) = 512
Mr = 116.16	Dx = 1.173 Mg m^−3
Monoclinic, C2/c	Melting point = 376–377 K
a = 18.321 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.015 (2) Å	µ = 0.09 mm^−1
c = 7.201 (2) Å	T = 173 K
β = 95.28 (2)°	Lozenge. Largest face is {100}; others are {110} and {111}., colorless
V = 1315.7 (5) Å^3	0.50 × 0.33 × 0.17 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	1159 independent reflections
Radiation source: fine-focus sealed tube	950 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 2.3°
ϕ and ω scans with 1.0° steps	h = −21→21
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −11→11
Tmin = 0.97, Tmax = 0.99	l = −8→8
2102 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.042P)^2 + 0.4P] where P = (Fo^2 + 2Fc^2)/3
1159 reflections	(Δ/σ)max < 0.001
90 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 20 s. The number of scan sets measured was 4; the total number of frames measured was 387.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.20979 (8)	0.38598 (11)	0.35850 (18)	0.0450 (4)	0.938 (2)
H01	0.2278	0.4592	0.3290	0.067*
O2	0.24125 (8)	0.1181 (2)	0.2722 (2)	0.0493 (6)	0.938 (2)
H02	0.2570	0.1333	0.3834	0.074*
C1	0.17524 (7)	0.32265 (13)	0.19511 (16)	0.0358 (4)	0.938 (2)
H1A	0.2068	0.3354	0.0904	0.043*	0.938 (2)
C2	0.17010 (7)	0.17555 (13)	0.23531 (17)	0.0386 (4)	0.938 (2)
H2A	0.1421	0.1627	0.3468	0.046*	0.938 (2)
C3	0.13133 (9)	0.10168 (16)	0.0708 (2)	0.0468 (4)	0.938 (2)
H3E	0.1251	0.0069	0.1052	0.056*	0.938 (2)
H3A	0.1622	0.1045	−0.0351	0.056*	0.938 (2)
C4	0.05679 (8)	0.16137 (17)	0.0100 (2)	0.0559 (5)	0.938 (2)
H4A	0.0236	0.1473	0.1091	0.067*	0.938 (2)
H4E	0.0354	0.1153	−0.1040	0.067*	0.938 (2)
C5	0.06269 (10)	0.30995 (18)	−0.0291 (3)	0.0558 (5)	0.938 (2)
H5E	0.0130	0.3477	−0.0590	0.067*	0.938 (2)
H5A	0.0909	0.3237	−0.1384	0.067*	0.938 (2)
C6	0.10057 (13)	0.38214 (17)	0.1392 (3)	0.0480 (9)	0.938 (2)
H6E	0.1060	0.4778	0.1089	0.058*	0.938 (2)
H6A	0.0699	0.3756	0.2451	0.058*	0.938 (2)
O1X	0.1916 (7)	0.3768 (13)	0.4050 (15)	0.028 (5)*	0.062 (2)
O2X	0.2458 (8)	0.1386 (16)	0.259 (2)	0.045 (11)*	0.062 (2)
C1X	0.1470 (5)	0.2955 (10)	0.2762 (11)	0.025 (5)*	0.062 (2)
H1AX	0.1213	0.2312	0.3429	0.030*	0.062 (2)
C2X	0.1950 (4)	0.2216 (11)	0.1489 (13)	0.025 (4)*	0.062 (2)
H2AX	0.2207	0.2859	0.0823	0.029*	0.062 (2)
C3X	0.1470 (7)	0.1340 (10)	0.0104 (15)	0.018 (5)*	0.062 (2)
H3AX	0.1215	0.0690	0.0764	0.021*	0.062 (2)
H3EX	0.1767	0.0870	−0.0684	0.021*	0.062 (2)
C4X	0.0923 (6)	0.2234 (13)	−0.1080 (12)	0.032 (5)*	0.062 (2)
H4AX	0.1179	0.2873	−0.1758	0.038*	0.062 (2)
H4EX	0.0626	0.1694	−0.1955	0.038*	0.062 (2)
C5X	0.0443 (5)	0.2973 (16)	0.0193 (19)	0.031 (7)*	0.062 (2)
H5AX	0.0181	0.2334	0.0854	0.038*	0.062 (2)
H5EX	0.0098	0.3524	−0.0540	0.038*	0.062 (2)
C6X	0.0923 (7)	0.3849 (12)	0.1579 (18)	0.023 (10)*	0.062 (2)
H6AX	0.1178	0.4499	0.0919	0.028*	0.062 (2)
H6EX	0.0626	0.4319	0.2367	0.028*	0.062 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0569 (8)	0.0408 (7)	0.0338 (6)	−0.0107 (5)	−0.0144 (6)	0.0010 (4)
O2	0.0596 (10)	0.0477 (8)	0.0371 (8)	0.0134 (5)	−0.0144 (5)	−0.0028 (5)
C1	0.0397 (7)	0.0394 (8)	0.0262 (6)	−0.0052 (6)	−0.0079 (6)	0.0008 (5)
C2	0.0426 (8)	0.0404 (8)	0.0313 (7)	−0.0013 (6)	−0.0044 (6)	0.0011 (6)
C3	0.0571 (10)	0.0437 (9)	0.0381 (8)	−0.0088 (7)	−0.0033 (7)	−0.0041 (7)
C4	0.0481 (9)	0.0703 (11)	0.0467 (9)	−0.0157 (8)	−0.0095 (7)	−0.0101 (7)
C5	0.0472 (9)	0.0670 (12)	0.0490 (9)	0.0037 (9)	−0.0186 (9)	−0.0005 (9)
C6	0.0476 (11)	0.0499 (14)	0.0439 (10)	0.0051 (7)	−0.0107 (8)	−0.0021 (6)

Geometric parameters (Å, º)

O1—C1	1.4319 (15)	C6—H6A	0.9900
O1—H01	0.8400	O1X—C1X	1.4324
O2—C2	1.4272 (17)	O2X—C2X	1.4312
O2—H02	0.8400	C1X—C2X	1.5196
C1—C2	1.506 (2)	C1X—C6X	1.5409
C1—C6	1.512 (2)	C1X—H1AX	0.9530
C1—H1A	1.0000	C2X—C3X	1.5420
C2—C3	1.5166 (18)	C2X—H2AX	0.9530
C2—H2A	1.0000	C3X—C4X	1.5408
C3—C4	1.518 (2)	C3X—H3AX	0.9531
C3—H3E	0.9900	C3X—H3EX	0.9473
C3—H3A	0.9900	C4X—C5X	1.5194
C4—C5	1.520 (3)	C4X—H4AX	0.9529
C4—H4A	0.9900	C4X—H4EX	0.9611
C4—H4E	0.9900	C5X—C6X	1.5420
C5—C6	1.523 (2)	C5X—H5AX	0.9529
C5—H5E	0.9900	C5X—H5EX	0.9606
C5—H5A	0.9900	C6X—H6AX	0.9531
C6—H6E	0.9900	C6X—H6EX	0.9471
O1—C1—C2	107.83 (10)	O1X—C1X—C2X	109.9
O1—C1—C6	111.40 (13)	O1X—C1X—C6X	109.3
C2—C1—C6	111.44 (13)	C2X—C1X—C6X	109.4
O1—C1—H1A	108.7	O1X—C1X—H1AX	109.7
C2—C1—H1A	108.7	C2X—C1X—H1AX	108.4
C6—C1—H1A	108.7	C6X—C1X—H1AX	110.1
O2—C2—C1	110.97 (14)	O2X—C2X—C1X	109.4
O2—C2—C3	107.63 (11)	O2X—C2X—C3X	109.3
C1—C2—C3	111.11 (11)	C1X—C2X—C3X	109.9
O2—C2—H2A	109.0	O2X—C2X—H2AX	110.1
C1—C2—H2A	109.0	C1X—C2X—H2AX	108.4
C3—C2—H2A	109.0	C3X—C2X—H2AX	109.7
C2—C3—C4	112.18 (12)	C4X—C3X—C2X	109.3
C2—C3—H3E	109.2	C4X—C3X—H3AX	110.4
C4—C3—H3E	109.2	C2X—C3X—H3AX	110.0
C2—C3—H3A	109.2	C4X—C3X—H3EX	109.7
C4—C3—H3A	109.2	C2X—C3X—H3EX	110.2
H3E—C3—H3A	107.9	H3AX—C3X—H3EX	107.1
C3—C4—C5	111.20 (13)	C5X—C4X—C3X	109.4
C3—C4—H4A	109.4	C5X—C4X—H4AX	108.7
C5—C4—H4A	109.4	C3X—C4X—H4AX	110.4
C3—C4—H4E	109.4	C5X—C4X—H4EX	110.2
C5—C4—H4E	109.4	C3X—C4X—H4EX	109.6
H4A—C4—H4E	108.0	H4AX—C4X—H4EX	108.5
C4—C5—C6	110.63 (14)	C4X—C5X—C6X	109.9
C4—C5—H5E	109.5	C4X—C5X—H5AX	108.7
C6—C5—H5E	109.5	C6X—C5X—H5AX	110.0
C4—C5—H5A	109.5	C4X—C5X—H5EX	109.7
C6—C5—H5A	109.5	C6X—C5X—H5EX	109.6
H5E—C5—H5A	108.1	H5AX—C5X—H5EX	108.9
C1—C6—C5	111.08 (17)	C1X—C6X—C5X	109.3
C1—C6—H6E	109.4	C1X—C6X—H6AX	110.4
C5—C6—H6E	109.4	C5X—C6X—H6AX	110.0
C1—C6—H6A	109.4	C1X—C6X—H6EX	109.7
C5—C6—H6A	109.4	C5X—C6X—H6EX	110.2
H6E—C6—H6A	108.0	H6AX—C6X—H6EX	107.2
O1—C1—C2—O2	−62.45 (15)	O1X—C1X—C2X—O2X	60.0
C6—C1—C2—O2	175.00 (13)	C6X—C1X—C2X—O2X	180.0
O1—C1—C2—C3	177.84 (11)	O1X—C1X—C2X—C3X	180.0
C6—C1—C2—C3	55.29 (18)	C6X—C1X—C2X—C3X	−60.0
O2—C2—C3—C4	−175.81 (16)	O2X—C2X—C3X—C4X	180.0
C1—C2—C3—C4	−54.13 (17)	C1X—C2X—C3X—C4X	60.0
C2—C3—C4—C5	54.16 (18)	C2X—C3X—C4X—C5X	−59.7
C3—C4—C5—C6	−54.9 (2)	C3X—C4X—C5X—C6X	60.0
O1—C1—C6—C5	−177.32 (16)	O1X—C1X—C6X—C5X	−180.0
C2—C1—C6—C5	−56.8 (2)	C2X—C1X—C6X—C5X	59.7
C4—C5—C6—C1	56.4 (3)	C4X—C5X—C6X—C1X	−60.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O2^i	0.84	1.86	2.6928 (19)	171
O2—H02···O1^ii	0.84	1.91	2.7274 (18)	164
O1—H01···O2X^i	0.84	1.98	2.81 (3)	171
O2—H02···O1X^ii	0.84	1.72	2.528 (10)	161

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1.

(k99095) rac-trans-1,2-cyclohexanediol

Crystal data

C6H12O2	F(000) = 512
Mr = 116.16	Dx = 1.148 Mg m^−3
Monoclinic, C2/c	Melting point = 376–377 K
a = 18.578 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.007 (3) Å	µ = 0.08 mm^−1
c = 7.272 (2) Å	T = 299 K
β = 96.32 (2)°	Lozenge. Largest face is {100}; others are {110} and {111}., colorless
V = 1343.7 (7) Å^3	0.25 × 0.19 × 0.05 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	1182 independent reflections
Radiation source: fine-focus sealed tube	856 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 2.3°
ϕ and ω scans with 2.0° steps	h = −22→21
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −11→11
Tmin = 0.98, Tmax = 0.99	l = −8→8
2285 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.057P)^2 + 0.3P] where P = (Fo^2 + 2Fc^2)/3
1182 reflections	(Δ/σ)max < 0.001
90 parameters	Δρmax = 0.10 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 80 s. The number of scan sets measured was 3; the total number of frames measured was 217.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.21017 (10)	0.38595 (14)	0.3575 (2)	0.0708 (5)	0.932 (3)
H01	0.2273	0.4576	0.3289	0.106*
O2	0.24052 (11)	0.1182 (2)	0.2725 (2)	0.0773 (7)	0.932 (3)
H02	0.2566	0.1350	0.3796	0.116*
C1	0.17503 (8)	0.32267 (16)	0.1959 (2)	0.0558 (5)	0.932 (3)
H1A	0.2049	0.3357	0.0944	0.067*	0.932 (3)
C2	0.17083 (9)	0.17609 (16)	0.2340 (2)	0.0594 (5)	0.932 (3)
H2A	0.1442	0.1632	0.3417	0.071*	0.932 (3)
C3	0.13149 (12)	0.10288 (19)	0.0714 (3)	0.0725 (6)	0.932 (3)
H3E	0.1258	0.0099	0.1045	0.087*	0.932 (3)
H3A	0.1605	0.1059	−0.0316	0.087*	0.932 (3)
C4	0.05785 (11)	0.1620 (2)	0.0115 (3)	0.0897 (7)	0.932 (3)
H4E	0.0365	0.1169	−0.0994	0.108*	0.932 (3)
H4A	0.0265	0.1477	0.1078	0.108*	0.932 (3)
C5	0.06293 (14)	0.3096 (2)	−0.0264 (4)	0.0867 (7)	0.932 (3)
H5E	0.0146	0.3462	−0.0546	0.104*	0.932 (3)
H5A	0.0891	0.3235	−0.1331	0.104*	0.932 (3)
C6	0.10141 (16)	0.3815 (2)	0.1391 (4)	0.0732 (10)	0.932 (3)
H6E	0.1066	0.4752	0.1090	0.088*	0.932 (3)
H6A	0.0724	0.3758	0.2419	0.088*	0.932 (3)
O1X	0.1924 (8)	0.3760 (14)	0.4062 (16)	0.039 (6)*	0.068 (3)
O2X	0.2503 (8)	0.1449 (17)	0.250 (2)	0.059 (9)*	0.068 (3)
C1X	0.1484 (5)	0.2930 (11)	0.2783 (13)	0.040 (6)*	0.068 (3)
H1AX	0.1251	0.2256	0.3453	0.049*	0.068 (3)
C2X	0.1964 (5)	0.2252 (11)	0.1453 (14)	0.033 (5)*	0.068 (3)
H2AX	0.2197	0.2926	0.0783	0.039*	0.068 (3)
C3X	0.1491 (7)	0.1358 (11)	0.0077 (16)	0.035 (6)*	0.068 (3)
H3AX	0.1260	0.0677	0.0740	0.042*	0.068 (3)
H3EX	0.1789	0.0926	−0.0747	0.042*	0.068 (3)
C4X	0.0911 (7)	0.2223 (14)	−0.1045 (14)	0.044 (5)*	0.068 (3)
H4AX	0.1142	0.2893	−0.1727	0.052*	0.068 (3)
H4EX	0.0618	0.1672	−0.1915	0.052*	0.068 (3)
C5X	0.0431 (5)	0.2901 (19)	0.028 (2)	0.069 (12)*	0.068 (3)
H5AX	0.0193	0.2230	0.0950	0.083*	0.068 (3)
H5EX	0.0065	0.3434	−0.0409	0.083*	0.068 (3)
C6X	0.0904 (7)	0.3795 (14)	0.166 (2)	0.051 (12)*	0.068 (3)
H6AX	0.1135	0.4476	0.0997	0.061*	0.068 (3)
H6EX	0.0606	0.4227	0.2485	0.061*	0.068 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0941 (12)	0.0597 (9)	0.0521 (9)	−0.0155 (7)	−0.0210 (9)	0.0013 (6)
O2	0.0976 (12)	0.0677 (10)	0.0599 (10)	0.0219 (9)	−0.0214 (8)	−0.0045 (7)
C1	0.0647 (10)	0.0561 (10)	0.0429 (9)	−0.0067 (8)	−0.0105 (8)	0.0022 (7)
C2	0.0699 (10)	0.0561 (10)	0.0495 (10)	−0.0012 (9)	−0.0063 (8)	0.0004 (8)
C3	0.0925 (14)	0.0605 (11)	0.0611 (12)	−0.0129 (10)	−0.0060 (11)	−0.0065 (9)
C4	0.0800 (13)	0.1013 (16)	0.0818 (14)	−0.0225 (12)	−0.0182 (11)	−0.0155 (12)
C5	0.0762 (12)	0.0939 (17)	0.0814 (15)	0.0034 (13)	−0.0301 (13)	−0.0005 (14)
C6	0.0747 (14)	0.0701 (17)	0.0700 (14)	0.0075 (9)	−0.0144 (12)	−0.0019 (9)

Geometric parameters (Å, º)

O1—C1	1.4285 (18)	C6—H6A	0.9700
O1—H01	0.8200	O1X—C1X	1.4336
O2—C2	1.418 (2)	O2X—C2X	1.4336
O2—H02	0.8200	C1X—C6X	1.5434
C1—C2	1.497 (3)	C1X—C2X	1.5437
C1—C6	1.505 (3)	C1X—H1AX	0.9623
C1—H1A	0.9800	C2X—C3X	1.5433
C2—C3	1.510 (2)	C2X—H2AX	0.9623
C2—H2A	0.9800	C3X—C4X	1.5434
C3—C4	1.510 (3)	C3X—H3AX	0.9622
C3—H3E	0.9700	C3X—H3EX	0.9621
C3—H3A	0.9700	C4X—C5X	1.5435
C4—C5	1.507 (3)	C4X—H4AX	0.9623
C4—H4E	0.9700	C4X—H4EX	0.9619
C4—H4A	0.9700	C5X—C6X	1.5432
C5—C6	1.513 (3)	C5X—H5AX	0.9623
C5—H5E	0.9700	C5X—H5EX	0.9623
C5—H5A	0.9700	C6X—H6AX	0.9622
C6—H6E	0.9700	C6X—H6EX	0.9620
O1—C1—C2	108.08 (12)	O1X—C1X—C6X	109.4
O1—C1—C6	111.81 (16)	O1X—C1X—C2X	109.5
C2—C1—C6	111.73 (16)	C6X—C1X—C2X	109.5
O1—C1—H1A	108.4	O1X—C1X—H1AX	109.5
C2—C1—H1A	108.4	C6X—C1X—H1AX	109.5
C6—C1—H1A	108.4	C2X—C1X—H1AX	109.5
O2—C2—C1	111.82 (17)	O2X—C2X—C3X	109.4
O2—C2—C3	108.02 (14)	O2X—C2X—C1X	109.4
C1—C2—C3	111.16 (14)	C3X—C2X—C1X	109.5
O2—C2—H2A	108.6	O2X—C2X—H2AX	109.5
C1—C2—H2A	108.6	C3X—C2X—H2AX	109.5
C3—C2—H2A	108.6	C1X—C2X—H2AX	109.5
C2—C3—C4	112.39 (16)	C2X—C3X—C4X	109.4
C2—C3—H3E	109.1	C2X—C3X—H3AX	109.8
C4—C3—H3E	109.1	C4X—C3X—H3AX	109.8
C2—C3—H3A	109.1	C2X—C3X—H3EX	109.8
C4—C3—H3A	109.1	C4X—C3X—H3EX	109.8
H3E—C3—H3A	107.9	H3AX—C3X—H3EX	108.2
C5—C4—C3	111.32 (17)	C3X—C4X—C5X	109.5
C5—C4—H4E	109.4	C3X—C4X—H4AX	109.8
C3—C4—H4E	109.4	C5X—C4X—H4AX	109.8
C5—C4—H4A	109.4	C3X—C4X—H4EX	109.7
C3—C4—H4A	109.4	C5X—C4X—H4EX	109.8
H4E—C4—H4A	108.0	H4AX—C4X—H4EX	108.3
C4—C5—C6	110.76 (19)	C6X—C5X—C4X	109.5
C4—C5—H5E	109.5	C6X—C5X—H5AX	109.8
C6—C5—H5E	109.5	C4X—C5X—H5AX	109.8
C4—C5—H5A	109.5	C6X—C5X—H5EX	109.7
C6—C5—H5A	109.5	C4X—C5X—H5EX	109.8
H5E—C5—H5A	108.1	H5AX—C5X—H5EX	108.2
C1—C6—C5	111.6 (2)	C5X—C6X—C1X	109.4
C1—C6—H6E	109.3	C5X—C6X—H6AX	109.8
C5—C6—H6E	109.3	C1X—C6X—H6AX	109.8
C1—C6—H6A	109.3	C5X—C6X—H6EX	109.8
C5—C6—H6A	109.3	C1X—C6X—H6EX	109.8
H6E—C6—H6A	108.0	H6AX—C6X—H6EX	108.2
O1—C1—C2—O2	−61.5 (2)	O1X—C1X—C2X—O2X	60.0
C6—C1—C2—O2	175.11 (18)	C6X—C1X—C2X—O2X	180.0
O1—C1—C2—C3	177.71 (15)	O1X—C1X—C2X—C3X	180.0
C6—C1—C2—C3	54.3 (2)	C6X—C1X—C2X—C3X	−60.1
O2—C2—C3—C4	−176.7 (2)	O2X—C2X—C3X—C4X	180.0
C1—C2—C3—C4	−53.7 (2)	C1X—C2X—C3X—C4X	60.1
C2—C3—C4—C5	54.1 (3)	C2X—C3X—C4X—C5X	−60.0
C3—C4—C5—C6	−54.5 (3)	C3X—C4X—C5X—C6X	60.1
O1—C1—C6—C5	−177.1 (2)	C4X—C5X—C6X—C1X	−60.1
C2—C1—C6—C5	−55.9 (3)	O1X—C1X—C6X—C5X	−180.0
C4—C5—C6—C1	55.6 (4)	C2X—C1X—C6X—C5X	60.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O2^i	0.82	1.89	2.707 (2)	172
O2—H02···O1^ii	0.82	1.95	2.745 (2)	162
O1—H01···O2X^i	0.82	2.02	2.83 (3)	169
O2—H02···O1X^ii	0.82	1.74	2.525 (11)	161

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1.

(R,R-1,2-CHD) R,R-1,2-cyclohexanediol

Crystal data

C6H12O2	Dx = 1.194 Mg m^−3
Mr = 116.16	Melting point = 380–383 K
Trigonal, P3221	Mo Kα radiation, λ = 0.71073 Å
a = 10.183 (1) Å	µ = 0.09 mm^−1
c = 10.796 (1) Å	T = 173 K
V = 969.49 (16) Å^3	Block, colorless
Z = 6	0.20 × 0.20 × 0.20 mm
F(000) = 384

Data collection

Nonius KappaCCD diffractometer	677 independent reflections
Radiation source: fine-focus sealed tube	620 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 2.3°
ϕ and ω scans with 2.0° steps	h = −12→10
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.98, Tmax = 0.98	l = −12→12
4834 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.033P)^2 + 0.18P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
677 reflections	Δρmax = 0.13 e Å^−3
76 parameters	Δρmin = −0.11 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.039 (6)

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 60 s. The number of scan sets measured was 2; the total number of frames measured was 141.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.41961 (17)	−0.14658 (17)	0.26617 (11)	0.0368 (4)
H01	0.4552	−0.2025	0.2853	0.055*
O2	0.46388 (18)	0.14676 (15)	0.30653 (12)	0.0419 (4)
H02	0.4945	0.1325	0.2383	0.063*
C1	0.3594 (2)	−0.1146 (2)	0.37427 (16)	0.0303 (5)
H1A	0.4376	−0.0787	0.4413	0.036*
C2	0.3287 (2)	0.0122 (2)	0.34210 (16)	0.0298 (5)
H2A	0.2546	−0.0213	0.2720	0.036*
C3	0.2624 (3)	0.0516 (3)	0.45243 (19)	0.0424 (6)
H3E	0.2376	0.1303	0.4279	0.051*
H3A	0.3389	0.0938	0.5194	0.051*
C4	0.1203 (3)	−0.0867 (3)	0.5005 (2)	0.0562 (7)
H4E	0.0834	−0.0586	0.5752	0.067*
H4A	0.0399	−0.1226	0.4367	0.067*
C5	0.1523 (4)	−0.2133 (3)	0.5324 (3)	0.0655 (8)
H5E	0.0572	−0.3040	0.5593	0.079*
H5A	0.2255	−0.1809	0.6018	0.079*
C6	0.2171 (3)	−0.2531 (3)	0.4201 (2)	0.0467 (6)
H6E	0.2409	−0.3330	0.4432	0.056*
H6A	0.1406	−0.2932	0.3530	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0480 (9)	0.0445 (10)	0.0344 (7)	0.0356 (8)	0.0045 (7)	0.0042 (7)
O2	0.0489 (10)	0.0251 (7)	0.0404 (8)	0.0100 (7)	0.0131 (7)	−0.0032 (6)
C1	0.0347 (11)	0.0309 (11)	0.0272 (9)	0.0178 (9)	−0.0017 (9)	−0.0018 (8)
C2	0.0315 (11)	0.0251 (11)	0.0313 (9)	0.0129 (9)	0.0008 (8)	−0.0019 (9)
C3	0.0539 (15)	0.0332 (12)	0.0415 (10)	0.0228 (11)	0.0125 (11)	−0.0023 (10)
C4	0.0566 (16)	0.0459 (15)	0.0607 (14)	0.0216 (13)	0.0297 (13)	−0.0046 (12)
C5	0.081 (2)	0.0384 (15)	0.0695 (16)	0.0238 (14)	0.0417 (16)	0.0114 (13)
C6	0.0557 (15)	0.0310 (12)	0.0530 (13)	0.0213 (12)	0.0166 (12)	0.0052 (10)

Geometric parameters (Å, º)

O1—C1	1.429 (2)	C3—H3E	0.9900
O1—H01	0.8400	C3—H3A	0.9900
O2—C2	1.426 (2)	C4—C5	1.518 (4)
O2—H02	0.8400	C4—H4E	0.9900
C1—C2	1.513 (3)	C4—H4A	0.9900
C1—C6	1.513 (3)	C5—C6	1.529 (3)
C1—H1A	1.0000	C5—H5E	0.9900
C2—C3	1.518 (3)	C5—H5A	0.9900
C2—H2A	1.0000	C6—H6E	0.9900
C3—C4	1.519 (3)	C6—H6A	0.9900
C1—O1—H01	109.5	H3E—C3—H3A	108.0
C2—O2—H02	109.5	C5—C4—C3	110.8 (2)
O1—C1—C2	107.59 (14)	C5—C4—H4E	109.5
O1—C1—C6	112.00 (16)	C3—C4—H4E	109.5
C2—C1—C6	111.08 (18)	C5—C4—H4A	109.5
O1—C1—H1A	108.7	C3—C4—H4A	109.5
C2—C1—H1A	108.7	H4E—C4—H4A	108.1
C6—C1—H1A	108.7	C4—C5—C6	110.4 (2)
O2—C2—C1	111.66 (16)	C4—C5—H5E	109.6
O2—C2—C3	107.48 (16)	C6—C5—H5E	109.6
C1—C2—C3	110.74 (16)	C4—C5—H5A	109.6
O2—C2—H2A	109.0	C6—C5—H5A	109.6
C1—C2—H2A	109.0	H5E—C5—H5A	108.1
C3—C2—H2A	109.0	C1—C6—C5	110.58 (19)
C2—C3—C4	111.48 (18)	C1—C6—H6E	109.5
C2—C3—H3E	109.3	C5—C6—H6E	109.5
C4—C3—H3E	109.3	C1—C6—H6A	109.5
C2—C3—H3A	109.3	C5—C6—H6A	109.5
C4—C3—H3A	109.3	H6E—C6—H6A	108.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O2^i	0.84	1.91	2.7410 (18)	169
O2—H02···O1^ii	0.84	1.97	2.7866 (18)	166

Symmetry codes: (i) −x+1, −x+y, −z+2/3; (ii) x−y, −y, −z+1/3.

(k99094) R,R-1,2-cyclohexanediol

Crystal data

C6H12O2	Dx = 1.171 Mg m^−3
Mr = 116.16	Melting point = 380–383 K
Trigonal, P3221	Mo Kα radiation, λ = 0.71073 Å
a = 10.229 (1) Å	µ = 0.09 mm^−1
c = 10.909 (1) Å	T = 293 K
V = 988.51 (16) Å^3	Block, colorless
Z = 6	0.22 × 0.20 × 0.19 mm
F(000) = 384

Data collection

Nonius KappaCCD diffractometer	686 independent reflections
Radiation source: fine-focus sealed tube	601 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 2.3°
ϕ and ω scans with 2.0° steps	h = −12→12
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −9→9
Tmin = 0.98, Tmax = 0.98	l = −12→12
2294 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 0.029P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
686 reflections	Δρmax = 0.08 e Å^−3
88 parameters	Δρmin = −0.09 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (7)

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 60 s. The number of scan sets measured was 3; the total number of frames measured was 212.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.41912 (17)	−0.14589 (17)	0.26670 (11)	0.0594 (4)
H01	0.4537	−0.2004	0.2851	0.086 (8)*
O2	0.46423 (18)	0.14606 (14)	0.30693 (13)	0.0678 (5)
H02	0.4946	0.1311	0.2418	0.089 (9)*
C1	0.3602 (2)	−0.1135 (2)	0.37374 (15)	0.0462 (5)
H1A	0.4371	−0.0784	0.4382	0.056 (5)*
C2	0.3300 (2)	0.01262 (19)	0.34293 (14)	0.0459 (5)
H2A	0.2574	−0.0200	0.2752	0.045 (5)*
C3	0.2645 (3)	0.0517 (2)	0.45181 (19)	0.0633 (6)
H3E	0.2405	0.1286	0.4281	0.083 (8)*
H3A	0.3393	0.0927	0.5167	0.066 (6)*
C4	0.1234 (3)	−0.0852 (3)	0.4995 (2)	0.0745 (7)
H4E	0.0875	−0.0574	0.5718	0.089 (8)*
H4A	0.0448	−0.1204	0.4376	0.112 (10)*
C5	0.1550 (3)	−0.2106 (3)	0.5314 (3)	0.0896 (9)
H5E	0.0623	−0.2991	0.5576	0.109 (9)*
H5A	0.2265	−0.1789	0.5986	0.140 (14)*
C6	0.2192 (3)	−0.2500 (2)	0.4203 (2)	0.0696 (7)
H6E	0.2423	−0.3280	0.4427	0.102 (8)*
H6A	0.1441	−0.2895	0.3557	0.066 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0783 (9)	0.0697 (10)	0.0560 (8)	0.0563 (9)	0.0063 (7)	0.0061 (7)
O2	0.0799 (11)	0.0403 (7)	0.0669 (9)	0.0179 (7)	0.0200 (7)	−0.0044 (6)
C1	0.0527 (11)	0.0485 (10)	0.0436 (9)	0.0299 (9)	−0.0029 (8)	−0.0017 (8)
C2	0.0503 (10)	0.0395 (10)	0.0473 (9)	0.0219 (9)	0.0008 (8)	−0.0019 (8)
C3	0.0827 (16)	0.0535 (12)	0.0590 (10)	0.0380 (11)	0.0128 (11)	−0.0028 (10)
C4	0.0758 (16)	0.0722 (15)	0.0746 (14)	0.0363 (12)	0.0277 (14)	−0.0026 (12)
C5	0.105 (2)	0.0635 (15)	0.0958 (17)	0.0389 (16)	0.0463 (18)	0.0205 (14)
C6	0.0805 (16)	0.0475 (12)	0.0802 (14)	0.0316 (12)	0.0168 (13)	0.0074 (11)

Geometric parameters (Å, º)

O1—C1	1.427 (2)	C3—H3E	0.9700
O1—H01	0.8200	C3—H3A	0.9700
O2—C2	1.424 (2)	C4—C5	1.512 (3)
O2—H02	0.8200	C4—H4E	0.9700
C1—C2	1.507 (2)	C4—H4A	0.9700
C1—C6	1.509 (3)	C5—C6	1.525 (3)
C1—H1A	0.9800	C5—H5E	0.9700
C2—C3	1.512 (3)	C5—H5A	0.9700
C2—H2A	0.9800	C6—H6E	0.9700
C3—C4	1.515 (3)	C6—H6A	0.9700
C1—O1—H01	109.5	H3E—C3—H3A	107.9
C2—O2—H02	109.5	C5—C4—C3	110.7 (2)
O1—C1—C2	107.90 (13)	C5—C4—H4E	109.5
O1—C1—C6	112.35 (16)	C3—C4—H4E	109.5
C2—C1—C6	110.91 (17)	C5—C4—H4A	109.5
O1—C1—H1A	108.5	C3—C4—H4A	109.5
C2—C1—H1A	108.5	H4E—C4—H4A	108.1
C6—C1—H1A	108.5	C4—C5—C6	110.1 (2)
O2—C2—C1	111.71 (16)	C4—C5—H5E	109.6
O2—C2—C3	107.78 (15)	C6—C5—H5E	109.6
C1—C2—C3	111.00 (15)	C4—C5—H5A	109.6
O2—C2—H2A	108.8	C6—C5—H5A	109.6
C1—C2—H2A	108.8	H5E—C5—H5A	108.1
C3—C2—H2A	108.8	C1—C6—C5	111.22 (18)
C2—C3—C4	111.66 (18)	C1—C6—H6E	109.4
C2—C3—H3E	109.3	C5—C6—H6E	109.4
C4—C3—H3E	109.3	C1—C6—H6A	109.4
C2—C3—H3A	109.3	C5—C6—H6A	109.4
C4—C3—H3A	109.3	H6E—C6—H6A	108.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O2^i	0.82	1.96	2.7681 (17)	170
O2—H02···O1^ii	0.82	2.02	2.8171 (19)	164

Symmetry codes: (i) −x+1, −x+y, −z+2/3; (ii) x−y, −y, −z+1/3.