(Cyclo­pentane-1,1-di­yl)dimethanol

Betz, R.; Klüfers, P.; Mayer, P.

doi:10.1107/S1600536809001330

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o479

doi:10.1107/S1600536809001330

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(Cyclopentane-1,1-diyl)dimethanol

Richard Betz,^a Peter Klüfers ^a ^* and Peter Mayer ^a

^aLudwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5–13 (Haus D), 81377 München, Germany
^*Correspondence e-mail: kluef@cup.uni-muenchen.de

(Received 17 December 2008; accepted 12 January 2009; online 6 February 2009)

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 R₄⁴(8). The cyclopentane-ring adopts an envelope conformation (^C4E).

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, P 2₁ /n
a = 5.8614 (16) Å
b = 10.631 (3) Å
c = 11.917 (3) Å
β = 98.33 (2)°
V = 734.7 (3) Å³
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[F² > 2σ(F²)] = 0.061
wR(F²) = 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

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) -x+1, -y+1, -z; (ii) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001330/zl2170sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001330/zl2170Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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 top

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).

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	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].

(Cyclopentane-1,1-diyl)dimethanol top

Crystal data top

C₇H₁₄O₂	Z = 4
M_r = 130.18	F(000) = 288
Monoclinic, P2₁/n	D_x = 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 top

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

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0527P)²] where P = (F_o² + 2F_c²)/3
1692 reflections	(Δ/σ)_max < 0.001
85 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₇H₁₄O₂	V = 734.7 (3) Å³
M_r = 130.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.8614 (16) Å	µ = 0.08 mm⁻¹
b = 10.631 (3) Å	T = 200 K
c = 11.917 (3) Å	0.20 × 0.17 × 0.06 mm
β = 98.33 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	924 reflections with I > 2σ(I)
4224 measured reflections	R_int = 0.067
1692 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
1692 reflections	Δρ_min = −0.17 e Å⁻³
85 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₇H₁₄O₂
M_r	130.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	5.8614 (16), 10.631 (3), 11.917 (3)
β (°)	98.33 (2)
V (Å³)	734.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.17 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4224, 1692, 924
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.149, 1.01
No. of reflections	1692
No. of parameters	85
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.91	2.720 (2)	162.6
O2—H2···O1ⁱⁱ	0.84	1.88	2.691 (2)	160.5

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

Acknowledgements

The authors thank Professor Klapötke for generous allocation of diffractometer time and Sandra Albrecht for professional support.

References

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