Adamantane-1,2-diol

In the crystal structure of the title compound, C₁₀H₁₆O₂, the hydroxyl groups are involved in both intra- and inter­molecular hydrogen bonding. Mol­ecules are arranged in discrete layers propagated by a network of O—H...O hydrogen-bonding inter­actions. The asymmetric unit comprises one chiral mol­ecule but the presence of a crystallographic centre of inversion leads to racemic crystals.

Key indicators

• Single-crystal X-ray study
• T = 83 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.061
• wR factor = 0.176
• Data-to-parameter ratio = 26.1

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.684     1.000
            Tmin(prime) and Tmax expected:      0.967     0.991
            RR(prime) =      0.701
            Please check that your absorption correction is appropriate.
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      0.840
            Test value =      0.800
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.70
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       0.84 e/A   3

Author Response: The top peaks in the final differnce Fourier progressively decrease (0.84, 0.75, 0.63, 0.53, 0.44, 0.43....) and unfortunately while the first peak is quite high we were unable to describe it as anything that would be chemically sensible.

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.28

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEXII (Bruker 2004); cell refinement: APEXII and SAINT (Bruker 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and POV-RAY (Persistence of Vision, 2004); software used to prepare material for publication: enCIFer (Allen et al., 2004).

adamantane-1,2-diol

Crystal data

C10H16O2	F(000) = 736
Mr = 168.23	Dx = 1.339 Mg m^−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2252 reflections
a = 9.6159 (3) Å	θ = 3.4–32.6°
b = 20.6781 (7) Å	µ = 0.09 mm^−1
c = 8.3921 (2) Å	T = 83 K
V = 1668.67 (9) Å^3	Block, colourless
Z = 8	0.36 × 0.24 × 0.10 mm

Data collection

Bruker Kappa-APEX-II area-detector diffractometer	2845 independent reflections
Radiation source: fine-focus sealed tube	2252 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
φ and ω scans	θmax = 32.7°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
Tmin = 0.684, Tmax = 1.000	k = −30→31
41081 measured reflections	l = −11→12

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.176	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0791P)^2 + 1.9937P] where P = (Fo^2 + 2Fc^2)/3
2845 reflections	(Δ/σ)max = 0.001
109 parameters	Δρmax = 0.84 e Å^−3
0 restraints	Δρmin = −0.37 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
O1	−0.13529 (11)	0.53630 (5)	0.09461 (12)	0.0133 (2)
H1A	−0.2032	0.5204	0.1438	0.020*
O2	0.13649 (12)	0.51341 (5)	0.22384 (13)	0.0182 (3)
H2A	0.1086	0.5052	0.1312	0.027*
C1	−0.06880 (14)	0.58392 (6)	0.19276 (15)	0.0095 (2)
C2	0.03234 (15)	0.55025 (7)	0.30695 (16)	0.0134 (3)
H2B	−0.0214	0.5206	0.3782	0.016*
C3	0.10813 (15)	0.60078 (7)	0.41011 (16)	0.0146 (3)
H3A	0.1749	0.5786	0.4833	0.017*
C4	0.18742 (16)	0.64722 (8)	0.30032 (18)	0.0173 (3)
H4A	0.2563	0.6227	0.2367	0.021*
H4B	0.2382	0.6795	0.3653	0.021*
C5	0.08549 (16)	0.68195 (7)	0.18849 (17)	0.0163 (3)
H5A	0.1376	0.7126	0.1184	0.020*
C6	−0.02213 (17)	0.71906 (7)	0.28638 (18)	0.0179 (3)
H6A	−0.0885	0.7409	0.2140	0.021*
H6B	0.0250	0.7526	0.3509	0.021*
C7	−0.10082 (15)	0.67278 (7)	0.39624 (17)	0.0144 (3)
H7A	−0.1707	0.6974	0.4604	0.017*
C8	0.00006 (16)	0.63765 (7)	0.50756 (17)	0.0155 (3)
H8A	0.0472	0.6694	0.5773	0.019*
H8B	−0.0520	0.6071	0.5760	0.019*
C9	0.01004 (15)	0.63076 (7)	0.08472 (16)	0.0148 (3)
H9A	−0.0558	0.6524	0.0114	0.018*
H9B	0.0788	0.6067	0.0199	0.018*
C10	−0.17528 (15)	0.62165 (7)	0.29281 (17)	0.0140 (3)
H10A	−0.2271	0.5914	0.3622	0.017*
H10B	−0.2428	0.6432	0.2214	0.017*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0127 (5)	0.0181 (5)	0.0091 (4)	−0.0048 (4)	−0.0003 (3)	−0.0032 (3)
O2	0.0179 (5)	0.0219 (5)	0.0148 (5)	0.0098 (4)	−0.0063 (4)	−0.0083 (4)
C1	0.0095 (6)	0.0118 (6)	0.0072 (5)	−0.0010 (4)	−0.0006 (4)	−0.0009 (4)
C2	0.0155 (6)	0.0149 (6)	0.0098 (5)	0.0023 (5)	−0.0007 (5)	−0.0005 (4)
C3	0.0137 (6)	0.0194 (6)	0.0107 (6)	0.0041 (5)	−0.0013 (5)	−0.0002 (4)
C4	0.0126 (6)	0.0229 (7)	0.0163 (6)	−0.0009 (5)	0.0008 (5)	−0.0009 (5)
C5	0.0157 (6)	0.0197 (7)	0.0136 (6)	−0.0029 (5)	0.0011 (5)	0.0032 (5)
C6	0.0199 (7)	0.0148 (6)	0.0190 (7)	0.0000 (5)	0.0001 (5)	0.0019 (5)
C7	0.0134 (6)	0.0161 (6)	0.0136 (6)	0.0034 (5)	0.0010 (5)	−0.0005 (5)
C8	0.0161 (6)	0.0187 (6)	0.0117 (6)	0.0029 (5)	0.0009 (5)	−0.0006 (5)
C9	0.0152 (6)	0.0186 (6)	0.0104 (6)	−0.0024 (5)	0.0000 (5)	0.0020 (5)
C10	0.0115 (6)	0.0172 (6)	0.0133 (6)	0.0004 (5)	0.0003 (5)	−0.0016 (5)

Geometric parameters (Å, º)

O1—C1	1.4343 (15)	C5—C6	1.528 (2)
O1—H1A	0.8400	C5—C9	1.551 (2)
O2—C2	1.4387 (17)	C5—H5A	1.0000
O2—H2A	0.8400	C6—C7	1.529 (2)
C1—C9	1.5279 (18)	C6—H6A	0.9900
C1—C2	1.5327 (19)	C6—H6B	0.9900
C1—C10	1.5369 (19)	C7—C8	1.530 (2)
C2—C3	1.540 (2)	C7—C10	1.544 (2)
C2—H2B	1.0000	C7—H7A	1.0000
C3—C8	1.526 (2)	C8—H8A	0.9900
C3—C4	1.534 (2)	C8—H8B	0.9900
C3—H3A	1.0000	C9—H9A	0.9900
C4—C5	1.535 (2)	C9—H9B	0.9900
C4—H4A	0.9900	C10—H10A	0.9900
C4—H4B	0.9900	C10—H10B	0.9900
C1—O1—H1A	109.5	C9—C5—H5A	109.7
C2—O2—H2A	109.5	C5—C6—C7	110.18 (12)
O1—C1—C9	108.40 (10)	C5—C6—H6A	109.6
O1—C1—C2	109.27 (10)	C7—C6—H6A	109.6
C9—C1—C2	110.13 (11)	C5—C6—H6B	109.6
O1—C1—C10	111.43 (11)	C7—C6—H6B	109.6
C9—C1—C10	109.45 (11)	H6A—C6—H6B	108.1
C2—C1—C10	108.17 (10)	C6—C7—C8	110.58 (12)
O2—C2—C1	112.28 (10)	C6—C7—C10	108.60 (12)
O2—C2—C3	107.60 (11)	C8—C7—C10	108.19 (11)
C1—C2—C3	110.09 (11)	C6—C7—H7A	109.8
O2—C2—H2B	108.9	C8—C7—H7A	109.8
C1—C2—H2B	108.9	C10—C7—H7A	109.8
C3—C2—H2B	108.9	C3—C8—C7	109.98 (11)
C8—C3—C4	110.34 (12)	C3—C8—H8A	109.7
C8—C3—C2	108.53 (12)	C7—C8—H8A	109.7
C4—C3—C2	108.80 (11)	C3—C8—H8B	109.7
C8—C3—H3A	109.7	C7—C8—H8B	109.7
C4—C3—H3A	109.7	H8A—C8—H8B	108.2
C2—C3—H3A	109.7	C1—C9—C5	109.36 (11)
C3—C4—C5	110.04 (12)	C1—C9—H9A	109.8
C3—C4—H4A	109.7	C5—C9—H9A	109.8
C5—C4—H4A	109.7	C1—C9—H9B	109.8
C3—C4—H4B	109.7	C5—C9—H9B	109.8
C5—C4—H4B	109.7	H9A—C9—H9B	108.2
H4A—C4—H4B	108.2	C1—C10—C7	110.23 (11)
C6—C5—C4	109.80 (12)	C1—C10—H10A	109.6
C6—C5—C9	109.14 (12)	C7—C10—H10A	109.6
C4—C5—C9	108.82 (12)	C1—C10—H10B	109.6
C6—C5—H5A	109.7	C7—C10—H10B	109.6
C4—C5—H5A	109.7	H10A—C10—H10B	108.1
O1—C1—C2—O2	58.47 (14)	C5—C6—C7—C8	58.37 (15)
C9—C1—C2—O2	−60.49 (14)	C5—C6—C7—C10	−60.20 (15)
C10—C1—C2—O2	179.94 (11)	C4—C3—C8—C7	57.96 (15)
O1—C1—C2—C3	178.32 (11)	C2—C3—C8—C7	−61.17 (15)
C9—C1—C2—C3	59.36 (14)	C6—C7—C8—C3	−57.91 (15)
C10—C1—C2—C3	−60.21 (14)	C10—C7—C8—C3	60.90 (15)
O2—C2—C3—C8	−176.45 (11)	O1—C1—C9—C5	−178.82 (11)
C1—C2—C3—C8	60.90 (14)	C2—C1—C9—C5	−59.32 (14)
O2—C2—C3—C4	63.46 (14)	C10—C1—C9—C5	59.47 (14)
C1—C2—C3—C4	−59.19 (14)	C6—C5—C9—C1	−60.02 (14)
C8—C3—C4—C5	−58.53 (15)	C4—C5—C9—C1	59.79 (15)
C2—C3—C4—C5	60.44 (15)	O1—C1—C10—C7	−179.64 (10)
C3—C4—C5—C6	58.54 (16)	C9—C1—C10—C7	−59.76 (14)
C3—C4—C5—C9	−60.85 (15)	C2—C1—C10—C7	60.24 (14)
C4—C5—C6—C7	−58.44 (16)	C6—C7—C10—C1	59.48 (14)
C9—C5—C6—C7	60.76 (15)	C8—C7—C10—C1	−60.59 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.84	2.45	2.8688 (15)	112
O1—H1A···O2^i	0.84	2.02	2.8625 (15)	176
O2—H2A···O1^ii	0.84	2.10	2.8633 (14)	152

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