1-Hydroxy­diamantane

The molecule of the title compound, C₁₄H₂₀O, posseses normal geometrical parameters. The compound crystallizes in the uncommon space group P4₂/n and features discrete quartets of mol­ecules linked by O—H...O bonds into a loop.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.149
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.64 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1-Hydroxydiamantane

Crystal data

C14H20O	Melting point: 564 K
Mr = 204.30	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42/n	Cell parameters from 18440 reflections
a = 16.572 (2) Å	θ = 1.7–27.5°
c = 7.7879 (16) Å	µ = 0.08 mm^−1
V = 2138.8 (6) Å^3	T = 293 K
Z = 8	Prism, colorless
F(000) = 896	0.64 × 0.22 × 0.18 mm
Dx = 1.269 Mg m^−3

Data collection

Rigaku R-AXIS RAPID IP CCD diffractometer	2441 independent reflections
Radiation source: Rotating Anode	1899 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −21→21
Tmin = 0.952, Tmax = 0.986	k = −20→21
18440 measured reflections	l = −10→10

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2441 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃, 300 MHz): δ 2.16 (d, J = 12.61 Hz, 2H), 2.04 (m, 1H), 1.95 (s, 2H), 1.74 (m, 1H), 1.63 (m, 11H), 1.45 (d, J = 12.81 Hz, 2H), 1.40 (s, 1H)

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	0.21864 (6)	0.36342 (5)	0.25158 (12)	0.0373 (3)
H1A	0.1911	0.3231	0.2346	0.056*
C1	0.20814 (7)	0.41896 (7)	0.11212 (15)	0.0259 (3)
C2	0.13216 (7)	0.46972 (7)	0.14299 (16)	0.0285 (3)
H2A	0.0852	0.4339	0.1479	0.034*
C3	0.13844 (9)	0.51636 (8)	0.31214 (18)	0.0394 (3)
H3A	0.0896	0.5474	0.3306	0.047*
H3B	0.1445	0.4789	0.4069	0.047*
C4	0.21070 (9)	0.57251 (8)	0.30507 (18)	0.0412 (3)
H4A	0.2149	0.6025	0.4132	0.049*
C5	0.20162 (9)	0.63153 (8)	0.1562 (2)	0.0423 (4)
H5A	0.2480	0.6672	0.1522	0.051*
H5B	0.1537	0.6642	0.1729	0.051*
C6	0.19492 (7)	0.58492 (7)	−0.01275 (17)	0.0323 (3)
H6A	0.1886	0.6233	−0.1076	0.039*
C7	0.12217 (7)	0.52821 (7)	−0.00894 (17)	0.0305 (3)
H7A	0.0731	0.5602	0.0083	0.037*
C8	0.11517 (9)	0.48238 (8)	−0.17846 (18)	0.0398 (3)
H8A	0.0684	0.4472	−0.1755	0.048*
H8B	0.1083	0.5202	−0.2724	0.048*
C9	0.19141 (9)	0.43253 (8)	−0.20667 (17)	0.0396 (3)
H9A	0.1872	0.4027	−0.3150	0.047*
C10	0.26376 (9)	0.48820 (9)	−0.21231 (19)	0.0424 (4)
H10A	0.2579	0.5261	−0.3064	0.051*
H10B	0.3124	0.4570	−0.2314	0.051*
C11	0.27042 (7)	0.53398 (8)	−0.04300 (17)	0.0331 (3)
H11A	0.3175	0.5697	−0.0480	0.040*
C12	0.28047 (7)	0.47589 (7)	0.10885 (17)	0.0294 (3)
H12A	0.3298	0.4442	0.0923	0.035*
C14	0.20136 (8)	0.37350 (7)	−0.05767 (18)	0.0348 (3)
H14A	0.1553	0.3374	−0.0537	0.042*
H14C	0.2495	0.3412	−0.0753	0.042*
C13	0.28683 (8)	0.52240 (8)	0.27801 (19)	0.0391 (3)
H13C	0.2934	0.4848	0.3725	0.047*
H13A	0.3336	0.5575	0.2752	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0427 (5)	0.0279 (4)	0.0413 (6)	0.0002 (4)	−0.0042 (4)	0.0115 (4)
C1	0.0256 (5)	0.0231 (5)	0.0290 (6)	0.0002 (4)	−0.0012 (4)	0.0038 (4)
C2	0.0229 (6)	0.0301 (6)	0.0326 (6)	0.0000 (4)	0.0023 (4)	0.0036 (5)
C3	0.0439 (8)	0.0428 (7)	0.0315 (7)	0.0093 (6)	0.0074 (5)	0.0000 (5)
C4	0.0522 (8)	0.0366 (7)	0.0349 (7)	0.0035 (6)	−0.0043 (6)	−0.0105 (6)
C5	0.0491 (8)	0.0264 (6)	0.0515 (9)	0.0026 (5)	−0.0025 (6)	−0.0057 (6)
C6	0.0356 (6)	0.0248 (6)	0.0365 (7)	0.0024 (5)	0.0009 (5)	0.0055 (5)
C7	0.0267 (6)	0.0301 (6)	0.0347 (7)	0.0053 (4)	−0.0021 (5)	0.0032 (5)
C8	0.0440 (7)	0.0407 (7)	0.0348 (7)	0.0007 (6)	−0.0117 (6)	0.0026 (6)
C9	0.0513 (8)	0.0391 (7)	0.0283 (6)	0.0021 (6)	−0.0008 (5)	−0.0063 (5)
C10	0.0474 (8)	0.0441 (8)	0.0358 (7)	0.0037 (6)	0.0148 (6)	0.0036 (6)
C11	0.0286 (6)	0.0309 (6)	0.0398 (7)	−0.0036 (5)	0.0057 (5)	0.0057 (5)
C12	0.0212 (5)	0.0285 (6)	0.0385 (7)	0.0005 (4)	−0.0006 (5)	0.0013 (5)
C14	0.0378 (7)	0.0273 (6)	0.0393 (7)	0.0005 (5)	−0.0009 (5)	−0.0043 (5)
C13	0.0375 (7)	0.0363 (7)	0.0435 (8)	−0.0024 (5)	−0.0131 (6)	−0.0016 (6)

Geometric parameters (Å, º)

O1—C1	1.4342 (14)	C7—C8	1.5275 (19)
O1—H1A	0.8200	C7—H7A	0.9800
C1—C12	1.5256 (15)	C8—C9	1.5254 (19)
C1—C14	1.5260 (17)	C8—H8A	0.9700
C1—C2	1.5333 (15)	C8—H8B	0.9700
C2—C3	1.5308 (18)	C9—C10	1.514 (2)
C2—C7	1.5385 (17)	C9—C14	1.5267 (19)
C2—H2A	0.9800	C9—H9A	0.9800
C3—C4	1.5176 (19)	C10—C11	1.525 (2)
C3—H3A	0.9700	C10—H10A	0.9700
C3—H3B	0.9700	C10—H10B	0.9700
C4—C13	1.525 (2)	C11—C12	1.5339 (18)
C4—C5	1.524 (2)	C11—H11A	0.9800
C4—H4A	0.9800	C12—C13	1.5299 (19)
C5—C6	1.5299 (19)	C12—H12A	0.9800
C5—H5A	0.9700	C14—H14A	0.9700
C5—H5B	0.9700	C14—H14C	0.9700
C6—C11	1.5277 (17)	C13—H13C	0.9700
C6—C7	1.5289 (17)	C13—H13A	0.9700
C6—H6A	0.9800
C1—O1—H1A	109.5	C9—C8—C7	109.32 (10)
O1—C1—C12	108.31 (9)	C9—C8—H8A	109.8
O1—C1—C14	110.38 (9)	C7—C8—H8A	109.8
C12—C1—C14	110.40 (10)	C9—C8—H8B	109.8
O1—C1—C2	109.45 (9)	C7—C8—H8B	109.8
C12—C1—C2	107.98 (9)	H8A—C8—H8B	108.3
C14—C1—C2	110.26 (9)	C10—C9—C8	109.29 (11)
C3—C2—C1	110.86 (10)	C10—C9—C14	109.09 (11)
C3—C2—C7	110.55 (10)	C8—C9—C14	109.09 (11)
C1—C2—C7	108.26 (9)	C10—C9—H9A	109.8
C3—C2—H2A	109.0	C8—C9—H9A	109.8
C1—C2—H2A	109.0	C14—C9—H9A	109.8
C7—C2—H2A	109.0	C9—C10—C11	109.59 (10)
C4—C3—C2	109.39 (10)	C9—C10—H10A	109.8
C4—C3—H3A	109.8	C11—C10—H10A	109.8
C2—C3—H3A	109.8	C9—C10—H10B	109.8
C4—C3—H3B	109.8	C11—C10—H10B	109.8
C2—C3—H3B	109.8	H10A—C10—H10B	108.2
H3A—C3—H3B	108.2	C10—C11—C6	110.42 (11)
C3—C4—C13	108.90 (11)	C10—C11—C12	111.24 (10)
C3—C4—C5	110.07 (12)	C6—C11—C12	108.47 (10)
C13—C4—C5	109.03 (12)	C10—C11—H11A	108.9
C3—C4—H4A	109.6	C6—C11—H11A	108.9
C13—C4—H4A	109.6	C12—C11—H11A	108.9
C5—C4—H4A	109.6	C1—C12—C13	110.56 (10)
C4—C5—C6	109.71 (10)	C1—C12—C11	108.40 (9)
C4—C5—H5A	109.7	C13—C12—C11	110.80 (10)
C6—C5—H5A	109.7	C1—C12—H12A	109.0
C4—C5—H5B	109.7	C13—C12—H12A	109.0
C6—C5—H5B	109.7	C11—C12—H12A	109.0
H5A—C5—H5B	108.2	C1—C14—C9	110.50 (10)
C11—C6—C7	108.01 (10)	C1—C14—H14A	109.6
C11—C6—C5	110.62 (11)	C9—C14—H14A	109.6
C7—C6—C5	110.55 (11)	C1—C14—H14C	109.6
C11—C6—H6A	109.2	C9—C14—H14C	109.6
C7—C6—H6A	109.2	H14A—C14—H14C	108.1
C5—C6—H6A	109.2	C4—C13—C12	109.65 (10)
C8—C7—C6	110.41 (11)	C4—C13—H13C	109.7
C8—C7—C2	111.08 (10)	C12—C13—H13C	109.7
C6—C7—C2	108.50 (10)	C4—C13—H13A	109.7
C8—C7—H7A	108.9	C12—C13—H13A	109.7
C6—C7—H7A	108.9	H13C—C13—H13A	108.2
C2—C7—H7A	108.9
O1—C1—C2—C3	58.95 (12)	C14—C9—C10—C11	−59.20 (14)
C12—C1—C2—C3	−58.75 (13)	C9—C10—C11—C6	−60.59 (13)
C14—C1—C2—C3	−179.44 (10)	C9—C10—C11—C12	59.90 (14)
O1—C1—C2—C7	−179.62 (9)	C7—C6—C11—C10	59.39 (13)
C12—C1—C2—C7	62.68 (12)	C5—C6—C11—C10	−179.51 (11)
C14—C1—C2—C7	−58.02 (12)	C7—C6—C11—C12	−62.75 (13)
C1—C2—C3—C4	60.39 (13)	C5—C6—C11—C12	58.36 (13)
C7—C2—C3—C4	−59.68 (13)	O1—C1—C12—C13	−59.78 (12)
C2—C3—C4—C13	−60.08 (14)	C14—C1—C12—C13	179.26 (9)
C2—C3—C4—C5	59.39 (14)	C2—C1—C12—C13	58.66 (12)
C3—C4—C5—C6	−59.30 (14)	O1—C1—C12—C11	178.59 (9)
C13—C4—C5—C6	60.10 (14)	C14—C1—C12—C11	57.62 (12)
C4—C5—C6—C11	−60.27 (14)	C2—C1—C12—C11	−62.98 (12)
C4—C5—C6—C7	59.32 (14)	C10—C11—C12—C1	−58.34 (13)
C11—C6—C7—C8	−59.40 (13)	C6—C11—C12—C1	63.30 (12)
C5—C6—C7—C8	179.45 (10)	C10—C11—C12—C13	−179.83 (10)
C11—C6—C7—C2	62.55 (13)	C6—C11—C12—C13	−58.19 (12)
C5—C6—C7—C2	−58.60 (13)	O1—C1—C14—C9	−179.18 (10)
C3—C2—C7—C8	−179.56 (10)	C12—C1—C14—C9	−59.46 (13)
C1—C2—C7—C8	58.83 (13)	C2—C1—C14—C9	59.77 (13)
C3—C2—C7—C6	58.90 (13)	C10—C9—C14—C1	59.55 (13)
C1—C2—C7—C6	−62.71 (12)	C8—C9—C14—C1	−59.77 (14)
C6—C7—C8—C9	60.28 (14)	C3—C4—C13—C12	60.33 (14)
C2—C7—C8—C9	−60.14 (14)	C5—C4—C13—C12	−59.79 (14)
C7—C8—C9—C10	−59.85 (14)	C1—C12—C13—C4	−60.53 (14)
C7—C8—C9—C14	59.35 (14)	C11—C12—C13—C4	59.68 (14)
C8—C9—C10—C11	60.00 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O1^i	0.82	1.96	2.7581 (13)	166

Symmetry code: (i) −y+1/2, x, −z+1/2.