Acta Cryst. (2009). E65, o479 [ doi:10.1107/S1600536809001330 ]
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).
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).
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 1.2Ueq(C) for methylene groups and U(H) set to 1.5Ueq(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)).
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).
![[Figure 1]](./zl2170fig1thm.gif)
| 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. |
![[Figure 2]](./zl2170fig2thm.gif)
| 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. |
![[Figure 3]](./zl2170fig3thm.gif)
| Fig. 3. The packing of the title compound, viewed along [-1 0 0]. |
| 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 |
| 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 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 |
| C7H14O2 | V = 734.7 (3) Å3 |
| Mr = 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)° |
| Oxford Diffraction Xcalibur diffractometer | 924 reflections with I > 2σ(I) |
| 4224 measured reflections | Rint = 0.067 |
| 1692 independent reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.061 | H-atom parameters constrained |
| wR(F2) = 0.149 | Δρmax = 0.19 e Å−3 |
| S = 1.01 | Δρmin = −0.17 e Å−3 |
| 1692 reflections | Absolute structure: ? |
| 85 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| 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* |
| 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) |
| 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) |
| 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. |
| 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. |
The authors thank Professor Klapötke for generous allocation of diffractometer time and Sandra Albrecht for professional support.
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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 C4TC3 (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.