(Cyclo­pentane-1,1-di­yl)dimethanol

Abstract

In the title compound, C₇H₁₄O₂, co-operative eight-membered homodromic rings of O—H⋯O hydrogen bonds connect the mol­ecules into strands along [100]. According to graph-set analysis, the descriptor of these cycles is R ₄ ⁴(8). The cyclo­pentane-ring adopts an envelope conformation (^C4 E).

Related literature

The compound was synthesized according to a published procedure (Domin et al., 2005 ▶). For the influence of chelation to (semi-)metals on the geometry of bifunctional alcohols, see: Klüfers & Vogler (2007 ▶). For the structure of a related compound, see Wender et al. (1999 ▶). For details on graph-set analysis of hydrogen bonds, see Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For details of puckering analysis, see Cremer & Pople (1975 ▶).

Experimental

Crystal data

• C₇H₁₄O₂

• M _r = 130.18

• Monoclinic,

• a = 5.8614 (16) Å

• b = 10.631 (3) Å

• c = 11.917 (3) Å

• β = 98.33 (2)°

• V = 734.7 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.08 mm⁻¹

• T = 200 (2) K

• 0.20 × 0.17 × 0.06 mm

Data collection

• Oxford Diffraction Xcalibur diffractometer

• Absorption correction: none

• 4224 measured reflections

• 1692 independent reflections

• 924 reflections with I > 2σ(I)

• R _int = 0.067

Refinement

• R[F ² > 2σ(F ²)] = 0.061

• wR(F ²) = 0.149

• S = 1.01

• 1692 reflections

• 85 parameters

• H-atom parameters constrained

• Δρ_max = 0.19 e Å⁻³

• Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.91	2.720 (2)	163
O2—H2⋯O1ii	0.84	1.88	2.691 (2)	161

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

In a program focused on the influence of chelation to (semi-)metals on the geometry of bifunctional alcohols (Klüfers & Vogler, 2007), the structure of 1,1-bis(hydroxymethyl)cyclopentane was elucidated.

Neglecting the hydrogen atoms of the hydroxy groups, the molecule would show non-crystallographic C₂ symmetry (Fig. 1).

According to a conformational analysis (Cremer & Pople, 1975), the cyclopentane-moiety adopts an envelope conformation ^C4E (Q₂ = 0.404 (3) Å), which is slightly distorted towards a twist conformation ^C4T_C3 (φ₂ = 280 (4)°).

In the crystals structure, hydrogen bonds furnish the formation of cooperative eight-membered homodromic rings (Fig. 2). These connect the molecules to strands along [1 0 0]. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for this pattern is R₄⁴(8).

The molecular packing of the compound is shown in Figure 3.

Experimental

The compound was prepared upon reacting 1,4-dibromobutane with malonic acid diethylester under basic conditions according to a published procedure (Domin et al., 2005). Crystals suitable for X-ray analysis were obtained upon recrystallization of the crude reaction product from a boiling mixture of ethyl acetate - light petrol ether (1:1).

Refinement

All H-atoms were placed in calculated positions (C—H 0.99 Å and O—H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U_eq(C) for methylene groups and U(H) set to 1.5U_eq(O). Hydroxyl H atoms were allowed to rotate with a fixed angle around the C-O bond to best fit the experimental electron density (HFIX 147 in the SHELX program suite (Sheldrick, 2008)).

Figures

Fig. 1.

The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.

Fig. 2.

Hydrogen bonds in the crystal structure of the title compound, viewed along [0 1 0]. Symmetry operators: ix - 1, y, z; ii -x + 1, -y + 1, -z; iiix + 1, y, z.

Fig. 3.

The packing of the title compound, viewed along [-1 0 0].

Crystal data

C7H14O2	Z = 4
Mr = 130.18	F(000) = 288
Monoclinic, P21/n	Dx = 1.177 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.8614 (16) Å	θ = 4.6–27.5°
b = 10.631 (3) Å	µ = 0.08 mm−1
c = 11.917 (3) Å	T = 200 K
β = 98.33 (2)°	Platelet, colourless
V = 734.7 (3) Å3	0.20 × 0.17 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer	924 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
graphite	θmax = 27.5°, θmin = 4.6°
ω scans	h = −7→4
4224 measured reflections	k = −13→13
1692 independent reflections	l = −14→15

Refinement

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0527P)2] where P = (Fo2 + 2Fc2)/3
1692 reflections	(Δ/σ)max < 0.001
85 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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

	x	y	z	Uiso*/Ueq
O1	0.2142 (2)	0.49721 (17)	0.14033 (13)	0.0473 (5)
H1	0.2522	0.5090	0.0758	0.071*
O2	0.7532 (3)	0.48406 (16)	0.08445 (12)	0.0431 (5)
H2	0.8893	0.4984	0.1146	0.065*
C1	0.5747 (4)	0.41846 (19)	0.24878 (17)	0.0299 (5)
C2	0.7724 (4)	0.4594 (2)	0.34277 (18)	0.0381 (6)
H21	0.9204	0.4638	0.3122	0.046*
H22	0.7393	0.5432	0.3729	0.046*
C3	0.7843 (5)	0.3602 (2)	0.4357 (2)	0.0562 (8)
H31	0.8906	0.2912	0.4223	0.067*
H32	0.8361	0.3975	0.5112	0.067*
C4	0.5393 (6)	0.3131 (3)	0.4270 (2)	0.0586 (8)
H41	0.4413	0.3733	0.4619	0.070*
H42	0.5330	0.2302	0.4641	0.070*
C5	0.4640 (4)	0.3034 (2)	0.2995 (2)	0.0475 (7)
H51	0.2939	0.3064	0.2812	0.057*
H52	0.5198	0.2240	0.2696	0.057*
C6	0.4039 (4)	0.5258 (2)	0.22489 (19)	0.0363 (6)
H61	0.3447	0.5481	0.2960	0.044*
H62	0.4853	0.6002	0.2004	0.044*
C7	0.6631 (4)	0.3799 (2)	0.14014 (19)	0.0388 (6)
H71	0.7856	0.3158	0.1581	0.047*
H72	0.5356	0.3410	0.0880	0.047*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0243 (8)	0.0853 (13)	0.0320 (8)	0.0014 (8)	0.0036 (7)	0.0073 (9)
O2	0.0276 (8)	0.0721 (12)	0.0303 (8)	−0.0023 (9)	0.0060 (7)	0.0062 (8)
C1	0.0290 (11)	0.0332 (11)	0.0274 (11)	−0.0025 (10)	0.0043 (9)	−0.0028 (9)
C2	0.0331 (12)	0.0496 (14)	0.0308 (11)	−0.0007 (11)	0.0018 (10)	−0.0010 (10)
C3	0.074 (2)	0.0586 (17)	0.0326 (13)	0.0067 (16)	−0.0032 (14)	0.0047 (12)
C4	0.093 (2)	0.0465 (15)	0.0408 (14)	−0.0035 (16)	0.0266 (15)	0.0052 (12)
C5	0.0526 (16)	0.0417 (14)	0.0500 (15)	−0.0048 (13)	0.0139 (13)	0.0066 (12)
C6	0.0288 (11)	0.0470 (14)	0.0330 (11)	0.0021 (11)	0.0039 (10)	0.0001 (10)
C7	0.0348 (12)	0.0454 (13)	0.0370 (13)	0.0008 (11)	0.0074 (11)	−0.0068 (11)

Geometric parameters (Å, °)

O1—C6	1.421 (3)	C3—H31	0.9900
O1—H1	0.8400	C3—H32	0.9900
O2—C7	1.431 (3)	C4—C5	1.523 (4)
O2—H2	0.8400	C4—H41	0.9900
C1—C6	1.517 (3)	C4—H42	0.9900
C1—C7	1.519 (3)	C5—H51	0.9900
C1—C5	1.548 (3)	C5—H52	0.9900
C1—C2	1.553 (3)	C6—H61	0.9900
C2—C3	1.524 (3)	C6—H62	0.9900
C2—H21	0.9900	C7—H71	0.9900
C2—H22	0.9900	C7—H72	0.9900
C3—C4	1.510 (4)
C6—O1—H1	109.5	C5—C4—H41	111.2
C7—O2—H2	109.5	C3—C4—H42	111.2
C6—C1—C7	109.90 (18)	C5—C4—H42	111.2
C6—C1—C5	111.40 (18)	H41—C4—H42	109.1
C7—C1—C5	109.48 (18)	C4—C5—C1	104.99 (19)
C6—C1—C2	109.13 (17)	C4—C5—H51	110.7
C7—C1—C2	112.31 (17)	C1—C5—H51	110.7
C5—C1—C2	104.54 (18)	C4—C5—H52	110.7
C3—C2—C1	106.30 (19)	C1—C5—H52	110.7
C3—C2—H21	110.5	H51—C5—H52	108.8
C1—C2—H21	110.5	O1—C6—C1	113.57 (18)
C3—C2—H22	110.5	O1—C6—H61	108.9
C1—C2—H22	110.5	C1—C6—H61	108.9
H21—C2—H22	108.7	O1—C6—H62	108.9
C4—C3—C2	103.7 (2)	C1—C6—H62	108.9
C4—C3—H31	111.0	H61—C6—H62	107.7
C2—C3—H31	111.0	O2—C7—C1	112.37 (18)
C4—C3—H32	111.0	O2—C7—H71	109.1
C2—C3—H32	111.0	C1—C7—H71	109.1
H31—C3—H32	109.0	O2—C7—H72	109.1
C3—C4—C5	103.1 (2)	C1—C7—H72	109.1
C3—C4—H41	111.2	H71—C7—H72	107.9
C6—C1—C2—C3	125.3 (2)	C2—C1—C5—C4	19.5 (2)
C7—C1—C2—C3	−112.5 (2)	C7—C1—C6—O1	57.0 (2)
C5—C1—C2—C3	6.1 (2)	C5—C1—C6—O1	−64.6 (2)
C1—C2—C3—C4	−29.5 (2)	C2—C1—C6—O1	−179.48 (17)
C2—C3—C4—C5	41.6 (3)	C6—C1—C7—O2	53.2 (2)
C3—C4—C5—C1	−38.0 (3)	C5—C1—C7—O2	175.88 (19)
C6—C1—C5—C4	−98.3 (2)	C2—C1—C7—O2	−68.5 (2)
C7—C1—C5—C4	140.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.91	2.720 (2)	163
O2—H2···O1ii	0.84	1.88	2.691 (2)	161

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