Bi-1,1′-cyclo­heptane-1,1′-diol

Betz, R.; Klüfers, P.

doi:10.1107/S1600536807058345

Bi-1,1'-cycloheptane-1,1'-diol

The title compound, C₁₄H₂₆O₂, is a vicinal diol bearing two sterically demanding conformationally flexible cycloheptyl rings adjacent to the hydroxy groups. The molecule shows approximate non-crystallographic C₂ symmetry. Bond lengths and angles are normal. In the crystal structure, infinite chains are formed by alternating intra- and intermolecular hydrogen bonds between the hydroxy groups.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058345/ng2371sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058345/ng2371Isup2.hkl Contains datablock I

CCDC reference: 672971

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C)= 0.002 Å
R factor = 0.052
wR factor = 0.127
Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Comment top

Bis-1,1'-cycloheptyl-1,1'-diol was prepared as a chelating molecule bearing the sterically demanding but conformationally flexible cycloheptyl groups. In the molecule two cycloheptyl groups are connected by a single bond. The two C atoms participating in the connection are further substituted with a hydroxy group each thus comprising a vicinal diol. Both cycloheptane rings adopt a chair-like conformation (Fig. 1). Bond lengths and angles are normal.

In the crystal packing (Fig. 2), one-dimensional chains of hydrogen-bonded molecules (Fig. 3) are the dominant structural motif.

Related literature top

For the synthesis of the title compound, see: Corey et al. (1976).

Experimental top

The title compound was prepared in adoption of a published procedure (Corey et al., 1976) upon pinacolic coupling of cycloheptanone.

Crystals suitable for X-ray analysis were obtained after recrystallization from boiling diethylether/n-pentane.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-III (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
	Fig. 2. The packing of (I), viewed along [0 1 0].
	Fig. 3. An individual hydrogen-bonded chain.

Bi-1,1'-cycloheptane-1,1'-diol top

Crystal data top

C₁₄H₂₆O₂	F(000) = 1008
M_r = 226.35	D_x = 1.134 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	θ = 3.9–26.0°
a = 9.875 (1) Å	µ = 0.07 mm⁻¹
b = 12.3662 (12) Å	T = 200 K
c = 21.7093 (19) Å	Block, colourless
V = 2651.1 (4) Å³	0.41 × 0.35 × 0.22 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	2619 independent reflections
Radiation source: fine-focus sealed tube	2208 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω–scans	θ_max = 26.0°, θ_min = 4.3°
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	h = −11→12
T_min = 0.980, T_max = 0.987	k = −13→15
12976 measured reflections	l = −26→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: difference Fourier map
wR(F²) = 0.127	Only H-atom displacement parameters refined
S = 1.16	w = 1/[σ²(F_o²) + (0.0541P)² + 0.4645P] where P = (F_o² + 2F_c²)/3
2619 reflections	(Δ/σ)_max < 0.001
148 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₄H₂₆O₂	V = 2651.1 (4) Å³
M_r = 226.35	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.875 (1) Å	µ = 0.07 mm⁻¹
b = 12.3662 (12) Å	T = 200 K
c = 21.7093 (19) Å	0.41 × 0.35 × 0.22 mm

Data collection top

Nonius KappaCCD diffractometer	2619 independent reflections
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	2208 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.987	R_int = 0.051
12976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.127	Only H-atom displacement parameters refined
S = 1.16	Δρ_max = 0.21 e Å⁻³
2619 reflections	Δρ_min = −0.17 e Å⁻³
148 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.05372 (10)	0.31065 (9)	0.21196 (5)	0.0340 (3)
H801	−0.1253	0.3298	0.2298	0.0460 (10)*
O2	0.20358 (10)	0.34212 (10)	0.22483 (5)	0.0351 (3)
H802	0.1460	0.3084	0.2459	0.0460 (10)*
C1	−0.00279 (14)	0.39937 (11)	0.17517 (7)	0.0241 (3)
C14	−0.01382 (16)	0.50382 (12)	0.21354 (7)	0.0315 (4)
H141	−0.0933	0.4965	0.2410	0.0460 (10)*
H142	0.0673	0.5083	0.2402	0.0460 (10)*
C13	−0.02705 (18)	0.61143 (13)	0.17922 (9)	0.0401 (4)
H131	0.0110	0.6697	0.2053	0.0460 (10)*
H132	0.0276	0.6079	0.1411	0.0460 (10)*
C12	−0.17232 (19)	0.64067 (14)	0.16229 (10)	0.0471 (5)
H121	−0.2296	0.6327	0.1994	0.0460 (10)*
H122	−0.1749	0.7177	0.1500	0.0460 (10)*
C11	−0.23341 (19)	0.57329 (15)	0.11070 (9)	0.0458 (5)
H111	−0.1862	0.5917	0.0719	0.0460 (10)*
H112	−0.3295	0.5944	0.1058	0.0460 (10)*
C10	−0.22698 (16)	0.45112 (14)	0.11944 (8)	0.0373 (4)
H101	−0.2846	0.4163	0.0879	0.0460 (10)*
H102	−0.2651	0.4329	0.1603	0.0460 (10)*
C9	−0.08306 (15)	0.40386 (13)	0.11493 (7)	0.0301 (4)
H91	−0.0897	0.3296	0.0982	0.0460 (10)*
H92	−0.0310	0.4475	0.0849	0.0460 (10)*
C2	0.14850 (14)	0.36422 (12)	0.16421 (7)	0.0254 (3)
C3	0.23549 (15)	0.45530 (13)	0.13821 (7)	0.0302 (4)
H31	0.2413	0.5133	0.1695	0.0460 (10)*
H32	0.1887	0.4858	0.1018	0.0460 (10)*
C4	0.37994 (16)	0.42418 (15)	0.11911 (8)	0.0394 (4)
H41	0.4402	0.4872	0.1255	0.0460 (10)*
H42	0.4122	0.3652	0.1462	0.0460 (10)*
C5	0.39112 (18)	0.38754 (17)	0.05225 (8)	0.0470 (5)
H51	0.3473	0.4426	0.0258	0.0460 (10)*
H52	0.4882	0.3851	0.0409	0.0460 (10)*
C6	0.32847 (18)	0.27796 (16)	0.03777 (8)	0.0466 (5)
H61	0.3829	0.2213	0.0584	0.0460 (10)*
H62	0.3350	0.2655	−0.0072	0.0460 (10)*
C7	0.18045 (18)	0.26413 (15)	0.05714 (8)	0.0422 (4)
H71	0.1445	0.1972	0.0382	0.0460 (10)*
H72	0.1273	0.3257	0.0408	0.0460 (10)*
C8	0.15943 (17)	0.25790 (12)	0.12723 (8)	0.0342 (4)
H81	0.2355	0.2157	0.1447	0.0460 (10)*
H82	0.0758	0.2159	0.1348	0.0460 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0257 (6)	0.0342 (6)	0.0421 (7)	0.0008 (4)	0.0071 (5)	0.0105 (5)
O2	0.0247 (6)	0.0522 (7)	0.0285 (6)	−0.0008 (5)	−0.0035 (5)	0.0092 (5)
C1	0.0226 (7)	0.0252 (7)	0.0245 (7)	−0.0016 (6)	0.0009 (6)	0.0027 (6)
C14	0.0293 (8)	0.0370 (9)	0.0283 (8)	0.0006 (7)	0.0029 (6)	−0.0067 (7)
C13	0.0451 (10)	0.0283 (9)	0.0470 (10)	−0.0026 (7)	0.0071 (8)	−0.0079 (7)
C12	0.0503 (11)	0.0298 (9)	0.0611 (12)	0.0112 (8)	0.0109 (10)	0.0040 (8)
C11	0.0373 (10)	0.0494 (11)	0.0507 (11)	0.0142 (8)	−0.0017 (8)	0.0132 (9)
C10	0.0271 (9)	0.0443 (10)	0.0406 (9)	0.0032 (7)	−0.0076 (7)	0.0001 (8)
C9	0.0263 (8)	0.0342 (8)	0.0297 (8)	0.0016 (6)	−0.0048 (6)	−0.0039 (6)
C2	0.0229 (7)	0.0300 (8)	0.0233 (7)	0.0013 (6)	−0.0022 (6)	0.0017 (6)
C3	0.0247 (8)	0.0352 (9)	0.0308 (8)	−0.0045 (6)	0.0011 (6)	−0.0005 (7)
C4	0.0247 (8)	0.0541 (11)	0.0395 (10)	−0.0028 (7)	0.0041 (7)	0.0007 (8)
C5	0.0313 (9)	0.0723 (13)	0.0372 (10)	0.0043 (9)	0.0090 (8)	0.0032 (9)
C6	0.0440 (10)	0.0637 (12)	0.0321 (9)	0.0191 (9)	0.0039 (8)	−0.0071 (8)
C7	0.0415 (10)	0.0457 (10)	0.0395 (10)	0.0072 (8)	−0.0042 (8)	−0.0147 (8)
C8	0.0300 (8)	0.0293 (8)	0.0432 (10)	0.0036 (6)	0.0013 (7)	−0.0005 (7)

Geometric parameters (Å, º) top

O1—C1	1.4472 (17)	C9—H91	0.9900
O1—H801	0.8400	C9—H92	0.9900
O2—C2	1.4501 (17)	C2—C3	1.525 (2)
O2—H802	0.8400	C2—C8	1.544 (2)
C1—C9	1.530 (2)	C3—C4	1.534 (2)
C1—C14	1.541 (2)	C3—H31	0.9900
C1—C2	1.574 (2)	C3—H32	0.9900
C14—C13	1.531 (2)	C4—C5	1.525 (2)
C14—H141	0.9900	C4—H41	0.9900
C14—H142	0.9900	C4—H42	0.9900
C13—C12	1.524 (3)	C5—C6	1.522 (3)
C13—H131	0.9900	C5—H51	0.9900
C13—H132	0.9900	C5—H52	0.9900
C12—C11	1.521 (3)	C6—C7	1.531 (3)
C12—H121	0.9900	C6—H61	0.9900
C12—H122	0.9900	C6—H62	0.9900
C11—C10	1.524 (3)	C7—C8	1.538 (2)
C11—H111	0.9900	C7—H71	0.9900
C11—H112	0.9900	C7—H72	0.9900
C10—C9	1.540 (2)	C8—H81	0.9900
C10—H101	0.9900	C8—H82	0.9900
C10—H102	0.9900

C1—O1—H801	109.5	H91—C9—H92	107.4
C2—O2—H802	109.5	O2—C2—C3	105.30 (11)
O1—C1—C9	108.61 (12)	O2—C2—C8	106.56 (12)
O1—C1—C14	108.21 (12)	C3—C2—C8	113.40 (12)
C9—C1—C14	113.26 (12)	O2—C2—C1	105.72 (11)
O1—C1—C2	101.77 (11)	C3—C2—C1	112.75 (12)
C9—C1—C2	111.87 (12)	C8—C2—C1	112.34 (12)
C14—C1—C2	112.35 (12)	C2—C3—C4	116.00 (13)
C13—C14—C1	118.14 (13)	C2—C3—H31	108.3
C13—C14—H141	107.8	C4—C3—H31	108.3
C1—C14—H141	107.8	C2—C3—H32	108.3
C13—C14—H142	107.8	C4—C3—H32	108.3
C1—C14—H142	107.8	H31—C3—H32	107.4
H141—C14—H142	107.1	C5—C4—C3	113.52 (14)
C12—C13—C14	113.82 (14)	C5—C4—H41	108.9
C12—C13—H131	108.8	C3—C4—H41	108.9
C14—C13—H131	108.8	C5—C4—H42	108.9
C12—C13—H132	108.8	C3—C4—H42	108.9
C14—C13—H132	108.8	H41—C4—H42	107.7
H131—C13—H132	107.7	C6—C5—C4	115.57 (15)
C11—C12—C13	114.89 (14)	C6—C5—H51	108.4
C11—C12—H121	108.5	C4—C5—H51	108.4
C13—C12—H121	108.5	C6—C5—H52	108.4
C11—C12—H122	108.5	C4—C5—H52	108.4
C13—C12—H122	108.5	H51—C5—H52	107.4
H121—C12—H122	107.5	C5—C6—C7	115.52 (15)
C12—C11—C10	115.78 (15)	C5—C6—H61	108.4
C12—C11—H111	108.3	C7—C6—H61	108.4
C10—C11—H111	108.3	C5—C6—H62	108.4
C12—C11—H112	108.3	C7—C6—H62	108.4
C10—C11—H112	108.3	H61—C6—H62	107.5
H111—C11—H112	107.4	C6—C7—C8	113.98 (14)
C11—C10—C9	114.00 (14)	C6—C7—H71	108.8
C11—C10—H101	108.8	C8—C7—H71	108.8
C9—C10—H101	108.8	C6—C7—H72	108.8
C11—C10—H102	108.8	C8—C7—H72	108.8
C9—C10—H102	108.8	H71—C7—H72	107.7
H101—C10—H102	107.6	C7—C8—C2	118.76 (13)
C1—C9—C10	115.95 (13)	C7—C8—H81	107.6
C1—C9—H91	108.3	C2—C8—H81	107.6
C10—C9—H91	108.3	C7—C8—H82	107.6
C1—C9—H92	108.3	C2—C8—H82	107.6
C10—C9—H92	108.3	H81—C8—H82	107.1

O1—C1—C14—C13	−153.65 (13)	C14—C1—C2—C3	−51.89 (16)
C9—C1—C14—C13	−33.17 (19)	O1—C1—C2—C8	62.95 (14)
C2—C1—C14—C13	94.79 (16)	C9—C1—C2—C8	−52.83 (16)
C1—C14—C13—C12	86.06 (18)	C14—C1—C2—C8	178.48 (12)
C14—C13—C12—C11	−72.2 (2)	O2—C2—C3—C4	72.10 (16)
C13—C12—C11—C10	53.4 (2)	C8—C2—C3—C4	−44.03 (18)
C12—C11—C10—C9	−69.5 (2)	C1—C2—C3—C4	−173.12 (13)
O1—C1—C9—C10	75.89 (16)	C2—C3—C4—C5	89.91 (18)
C14—C1—C9—C10	−44.36 (18)	C3—C4—C5—C6	−70.9 (2)
C2—C1—C9—C10	−172.58 (13)	C4—C5—C6—C7	53.6 (2)
C11—C10—C9—C1	89.02 (18)	C5—C6—C7—C8	−70.2 (2)
O1—C1—C2—O2	−52.88 (13)	C6—C7—C8—C2	84.19 (19)
C9—C1—C2—O2	−168.66 (11)	O2—C2—C8—C7	−148.94 (14)
C14—C1—C2—O2	62.64 (15)	C3—C2—C8—C7	−33.56 (19)
O1—C1—C2—C3	−167.42 (12)	C1—C2—C8—C7	95.73 (16)
C9—C1—C2—C3	76.80 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H801···O2ⁱ	0.84	1.96	2.7889 (15)	168
O2—H802···O1	0.84	2.11	2.5856 (15)	116

Symmetry code: (i) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₆O₂
M_r	226.35
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	200
a, b, c (Å)	9.875 (1), 12.3662 (12), 21.7093 (19)
V (Å³)	2651.1 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.41 × 0.35 × 0.22

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Analytical (de Meulenaer & Tompa, 1965)
T_min, T_max	0.980, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	12976, 2619, 2208
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.127, 1.16
No. of reflections	2619
No. of parameters	148
H-atom treatment	Only H-atom displacement parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-III (Burnett & Johnson, 1996).