Dodeca­hydroxy­cyclo­hexane dihydrate

In the commercially available title compound, C₆H₁₂O₁₂·2H₂O, the dodeca­hydroxy­cyclo­hexane mol­ecule has an inversion center. The crystal packing is characterized by a strong O—H...O hydrogen bond involving the water mol­ecules, and the dodeca­hydroxy­cyclo­hexane mol­ecules are additionally linked by O—H...O hydrogen bonds of the hydroxyl groups, resulting in the formation of a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.091
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.97 Deg.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.67
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?
PLAT417_ALERT_2_C Short Inter D-H..H-D       H5     ..  H7B     ..       2.11 Ang.
PLAT725_ALERT_1_C D-H     Calc     0.82003, Rep     0.80000 Dev...       0.02 Ang.
              O2   -H2      1.555   1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Nonius, 1994); cell refinement: CAD-4 Software; data reduction: OpenMolEN (Nonius, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXL97.

Dodecahydroxycyclohexane dihydrate

Crystal data

C6H12O12·2H2O	Z = 1
Mr = 312.19	F(000) = 164
Triclinic, P1	Dx = 1.919 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1829 (8) Å	Cell parameters from 22 reflections
b = 7.0696 (8) Å	θ = 9–18°
c = 7.3023 (6) Å	µ = 0.20 mm^−1
α = 70.443 (8)°	T = 295 K
β = 80.153 (8)°	Plate, colourless
γ = 63.973 (10)°	0.47 × 0.43 × 0.10 mm
V = 270.16 (5) Å^3

Data collection

Nonius MACH3 diffractometer	893 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.010
Graphite monochromator	θmax = 25.0°, θmin = 3.0°
ω–2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = −7→8
Tmin = 0.945, Tmax = 0.976	l = −8→8
1046 measured reflections	3 standard reflections every 7200 min
948 independent reflections	intensity decay: 1.9%

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) = 0.091	w = 1/[σ^2(Fo^2) + (0.0441P)^2 + 0.2382P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
948 reflections	Δρmax = 0.36 e Å^−3
98 parameters	Δρmin = −0.43 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.155 (19)

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
O1	0.2756 (2)	0.2131 (2)	0.61259 (18)	0.0196 (3)
H1	0.3392	0.0804	0.6258	0.023*
O2	0.6829 (2)	0.12722 (19)	0.61615 (17)	0.0182 (3)
H2	0.7012	0.0875	0.7337	0.022*
O3	0.4065 (2)	0.3354 (2)	0.89185 (17)	0.0192 (3)
H3	0.3008	0.2894	0.9268	0.023*
O4	0.1347 (2)	0.6042 (2)	0.67023 (18)	0.0179 (3)
H4	0.1205	0.7020	0.5673	0.021*
O5	0.7677 (2)	0.4402 (2)	0.71644 (18)	0.0193 (3)
H5	0.8615	0.4998	0.6763	0.023*
O6	0.4379 (2)	0.7556 (2)	0.74223 (17)	0.0202 (4)
H6	0.4816	0.7043	0.8550	0.024*
O7	1.0816 (3)	0.1603 (2)	1.04555 (19)	0.0289 (4)
H7A	0.9602	0.2124	1.1401	0.035*
H7B	0.9742	0.2469	0.9401	0.035*
C1	0.4533 (3)	0.2953 (3)	0.5717 (2)	0.0143 (4)
C2	0.3803 (3)	0.4570 (3)	0.6963 (2)	0.0142 (4)
C3	0.5388 (3)	0.5886 (3)	0.6498 (2)	0.0145 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0200 (7)	0.0178 (6)	0.0249 (7)	−0.0116 (5)	0.0006 (5)	−0.0064 (5)
O2	0.0183 (7)	0.0165 (6)	0.0160 (6)	−0.0038 (5)	−0.0035 (5)	−0.0033 (5)
O3	0.0237 (7)	0.0247 (7)	0.0120 (6)	−0.0144 (6)	−0.0009 (5)	−0.0024 (5)
O4	0.0143 (6)	0.0195 (7)	0.0180 (6)	−0.0059 (5)	−0.0004 (5)	−0.0046 (5)
O5	0.0158 (6)	0.0220 (7)	0.0206 (7)	−0.0096 (5)	−0.0056 (5)	−0.0021 (5)
O6	0.0296 (8)	0.0189 (7)	0.0153 (6)	−0.0101 (6)	−0.0028 (5)	−0.0078 (5)
O7	0.0272 (8)	0.0337 (8)	0.0207 (7)	−0.0107 (6)	0.0012 (6)	−0.0051 (6)
C1	0.0137 (8)	0.0147 (8)	0.0156 (8)	−0.0068 (7)	−0.0019 (6)	−0.0038 (7)
C2	0.0140 (8)	0.0161 (8)	0.0120 (8)	−0.0061 (7)	−0.0012 (6)	−0.0031 (7)
C3	0.0161 (9)	0.0144 (8)	0.0148 (9)	−0.0065 (7)	−0.0024 (6)	−0.0053 (7)

Geometric parameters (Å, º)

O1—C1	1.402 (2)	O5—H5	0.8200
O1—H1	0.8200	O6—C3	1.408 (2)
O2—C1	1.397 (2)	O6—H6	0.8200
O2—H2	0.8200	O7—H7A	0.9621
O3—C2	1.393 (2)	O7—H7B	0.9548
O3—H3	0.8200	C1—C3^i	1.553 (2)
O4—C2	1.416 (2)	C1—C2	1.562 (2)
O4—H4	0.8200	C2—C3	1.554 (2)
O5—C3	1.390 (2)	C3—C1^i	1.553 (2)
C1—O1—H1	109.5	O3—C2—O4	107.37 (13)
C1—O2—H2	109.5	O3—C2—C3	107.66 (13)
C2—O3—H3	109.5	O4—C2—C3	109.92 (13)
C2—O4—H4	109.5	O3—C2—C1	108.62 (13)
C3—O5—H5	109.5	O4—C2—C1	109.99 (13)
C3—O6—H6	109.5	C3—C2—C1	113.08 (13)
H7A—O7—H7B	93.1	O5—C3—O6	111.14 (13)
O2—C1—O1	111.93 (13)	O5—C3—C1^i	111.13 (14)
O2—C1—C3^i	106.13 (13)	O6—C3—C1^i	106.69 (13)
O1—C1—C3^i	109.27 (13)	O5—C3—C2	107.33 (13)
O2—C1—C2	111.45 (13)	O6—C3—C2	109.66 (13)
O1—C1—C2	105.63 (13)	C1^i—C3—C2	110.93 (13)
C3^i—C1—C2	112.52 (13)
O2—C1—C2—O3	−53.70 (17)	O3—C2—C3—O5	50.92 (17)
O1—C1—C2—O3	68.08 (16)	O4—C2—C3—O5	167.58 (12)
C3^i—C1—C2—O3	−172.78 (13)	C1—C2—C3—O5	−69.07 (17)
O2—C1—C2—O4	−170.94 (12)	O3—C2—C3—O6	−69.91 (16)
O1—C1—C2—O4	−49.17 (17)	O4—C2—C3—O6	46.74 (17)
C3^i—C1—C2—O4	69.97 (17)	C1—C2—C3—O6	170.09 (13)
O2—C1—C2—C3	65.75 (18)	O3—C2—C3—C1^i	172.49 (13)
O1—C1—C2—C3	−172.48 (13)	O4—C2—C3—C1^i	−70.85 (17)
C3^i—C1—C2—C3	−53.3 (2)	C1—C2—C3—C1^i	52.50 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6^ii	0.82	2.00	2.791 (2)	161
O2—H2···O3	0.8	2.36	2.782 (2)	113
O2—H2···O7^iii	0.82	2.06	2.761 (2)	143
O3—H3···O7^iv	0.82	1.89	2.704 (2)	171
O4—H4···O2^i	0.82	2.09	2.768 (2)	140
O4—H4···O5^i	0.82	2.46	2.877 (2)	112
O5—H5···O1^v	0.82	2.56	2.931 (2)	109
O5—H5···O4^v	0.82	2.11	2.897 (2)	161
O5—H5···O1^i	0.82	2.35	2.748 (2)	110
O6—H6···O3^vi	0.82	1.97	2.769 (2)	163
O7—H7A···O4^vi	0.96	2.05	2.877 (2)	143
O7—H7A···O6^vi	0.96	2.40	3.211 (2)	142
O7—H7B···O5	0.95	1.96	2.916 (2)	175

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+2, −y, −z+2; (iv) x−1, y, z; (v) x+1, y, z; (vi) −x+1, −y+1, −z+2.