[(1R,3S)-2,2-Dichloro-3-(hy-droxy-meth-yl)cyclo-prop-yl]methanol.

The title compound, C(5)H(8)Cl(2)O(2), represents a meso isomer crystallizing in a chiral space group with two mol-ecules per asymmetric unit. The mol-ecules form helical associates with a pitch of 6.31 Å along the a axis via O-H⋯O hydrogen bonds. The overall three-dimesional supra-molecular architecture is stabilized by C-Cl⋯O halogen bonding, with a Cl⋯O separation of 3.139 (3) Å and a C-Cl⋯O angle of 162.5 (2)°.

Related literature

For background on this class of compounds, see: Kean et al. (2012 ▶); Lenhardt et al. (2009 ▶). For one-handed helical chains caused by hydrogen bonds, see: Abe et al. (2012 ▶). For the preparation of this type of compound, see: Kailani et al. (2012 ▶); Pustovit et al. (1994 ▶).

Experimental

Crystal data

C5H8Cl2O2

M = 171.02

Orthorhombic,

a = 6.3110 (13) Å

b = 15.429 (3) Å

c = 15.433 (3) Å

V = 1502.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.79 mm−1

T = 293 K

0.2 × 0.1 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (COLLECT; Nonius, 2004 ▶) T min = 0.91, T max = 0.96

6911 measured reflections

2628 independent reflections

1969 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.085

S = 1.03

2627 reflections

181 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1081 Friedel pairs

Flack parameter: 0.03 (9)

Data collection: COLLECT (Nonius, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000366/ld2090sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000366/ld2090Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000366/ld2090Isup3.cml

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

C5H8Cl2O2	Dx = 1.512 Mg m−3
Mr = 171.02	Melting point = 346–347 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2370 reflections
a = 6.3110 (13) Å	θ = 1.0–27.5°
b = 15.429 (3) Å	µ = 0.79 mm−1
c = 15.433 (3) Å	T = 293 K
V = 1502.7 (5) Å3	Chunk, colorless
Z = 8	0.2 × 0.1 × 0.05 mm
F(000) = 704

Nonius KappaCCD diffractometer	2628 independent reflections
Radiation source: fine-focus sealed tube	1969 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 9 pixels mm-1	θmax = 25.0°, θmin = 1.3°
CCD scans	h = −7→6
Absorption correction: multi-scan (COLLECT; Nonius, 2004)	k = −18→18
Tmin = 0.91, Tmax = 0.96	l = −12→18
6911 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0363P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.17 e Å−3
2627 reflections	Δρmin = −0.17 e Å−3
181 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0080 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1081 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.03 (9)

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.

	x	y	z	Uiso*/Ueq
Cl2B	0.87935 (18)	0.17519 (6)	0.46132 (7)	0.0716 (4)
Cl1B	1.21060 (18)	0.08413 (7)	0.55235 (8)	0.0763 (4)
Cl2A	1.4218 (2)	0.27973 (6)	0.07758 (7)	0.0795 (4)
Cl1A	1.08097 (18)	0.18830 (7)	0.16287 (8)	0.0769 (4)
O1B	1.2516 (5)	−0.04682 (18)	0.3348 (2)	0.0665 (8)
O1A	1.0243 (5)	0.40988 (19)	0.28993 (19)	0.0620 (8)
O2B	0.7810 (5)	−0.03519 (18)	0.6574 (2)	0.0690 (9)
C5B	0.8709 (7)	−0.0635 (2)	0.5790 (2)	0.0600 (11)
H5BA	0.8091	−0.1187	0.5625	0.072*
H5BB	1.0222	−0.0718	0.5864	0.072*
O2A	1.5018 (5)	0.08789 (19)	0.2961 (2)	0.0699 (9)
C5A	1.4000 (7)	0.1672 (2)	0.3187 (2)	0.0637 (11)
H5AA	1.4496	0.1865	0.3750	0.076*
H5AB	1.2481	0.1582	0.3223	0.076*
C3B	0.8318 (6)	0.0018 (2)	0.5091 (2)	0.0497 (9)
H3BA	0.6823	0.0172	0.5015	0.060*
C4A	1.1354 (6)	0.3326 (2)	0.3103 (3)	0.0583 (11)
H4AA	1.0382	0.2839	0.3078	0.070*
H4AB	1.1897	0.3365	0.3689	0.070*
C4B	1.1321 (7)	−0.0657 (2)	0.4107 (3)	0.0626 (11)
H4BA	1.2261	−0.0667	0.4604	0.075*
H4BB	1.0689	−0.1227	0.4051	0.075*
C2B	0.9584 (6)	0.0010 (2)	0.4257 (3)	0.0529 (10)
H2BB	0.8767	0.0159	0.3738	0.063*
C3A	1.4473 (6)	0.23491 (19)	0.2521 (3)	0.0548 (10)
H3AA	1.5983	0.2432	0.2399	0.066*
C1A	1.3052 (6)	0.2518 (2)	0.1778 (2)	0.0507 (10)
C2A	1.3162 (6)	0.3166 (2)	0.2490 (2)	0.0524 (9)
H2AB	1.3973	0.3688	0.2344	0.063*
C1B	0.9818 (6)	0.07341 (19)	0.4897 (2)	0.0486 (10)
H4	1.095 (6)	0.448 (2)	0.302 (2)	0.047 (13)*
H3	0.859 (6)	−0.054 (2)	0.697 (3)	0.060 (13)*
H2	1.424 (7)	0.051 (2)	0.310 (3)	0.068 (15)*
H1	1.181 (6)	−0.063 (2)	0.292 (3)	0.066 (14)*

	U11	U22	U33	U12	U13	U23
Cl2B	0.0888 (8)	0.0565 (5)	0.0694 (7)	0.0161 (6)	0.0126 (7)	0.0145 (5)
Cl1B	0.0631 (7)	0.0797 (6)	0.0862 (9)	−0.0072 (6)	−0.0204 (7)	−0.0111 (6)
Cl2A	0.1087 (10)	0.0682 (6)	0.0617 (7)	0.0140 (6)	0.0250 (8)	0.0129 (5)
Cl1A	0.0669 (7)	0.0800 (7)	0.0837 (8)	−0.0173 (6)	−0.0128 (7)	−0.0142 (6)
O1B	0.068 (2)	0.0746 (17)	0.057 (2)	−0.0007 (16)	0.0102 (19)	−0.0108 (16)
O1A	0.0628 (19)	0.0592 (18)	0.064 (2)	0.0011 (17)	0.0012 (17)	−0.0048 (14)
O2B	0.085 (2)	0.0726 (17)	0.049 (2)	0.0196 (17)	0.0000 (19)	0.0076 (15)
C5B	0.072 (3)	0.047 (2)	0.061 (3)	−0.0013 (19)	0.006 (3)	0.0043 (19)
O2A	0.078 (2)	0.0605 (18)	0.071 (2)	0.0117 (17)	0.0192 (19)	0.0079 (15)
C5A	0.073 (3)	0.070 (2)	0.048 (3)	0.016 (2)	0.005 (3)	0.0061 (19)
C3B	0.043 (2)	0.0554 (19)	0.051 (2)	0.0040 (17)	−0.0057 (19)	−0.0036 (18)
C4A	0.069 (3)	0.058 (2)	0.048 (3)	0.005 (2)	0.003 (2)	0.0028 (18)
C4B	0.073 (3)	0.057 (2)	0.058 (3)	0.007 (2)	−0.003 (3)	−0.0065 (19)
C2B	0.052 (2)	0.058 (2)	0.049 (2)	0.0065 (18)	−0.001 (2)	−0.0027 (17)
C3A	0.047 (2)	0.058 (2)	0.059 (3)	−0.0016 (19)	0.005 (2)	0.0018 (19)
C1A	0.054 (2)	0.053 (2)	0.045 (2)	−0.0014 (17)	0.003 (2)	0.0036 (18)
C2A	0.060 (2)	0.0474 (18)	0.050 (2)	−0.0061 (19)	0.004 (2)	−0.0014 (17)
C1B	0.053 (2)	0.0450 (19)	0.048 (2)	−0.0008 (17)	0.0006 (19)	0.0030 (16)

Cl2B—C1B	1.754 (3)	C5A—H5AB	0.9700
Cl1B—C1B	1.746 (4)	C3B—C1B	1.486 (5)
Cl2A—C1A	1.767 (4)	C3B—C2B	1.515 (5)
Cl1A—C1A	1.737 (4)	C3B—H3BA	0.9800
O1B—C4B	1.423 (5)	C4A—C2A	1.502 (5)
O1B—H1	0.84 (4)	C4A—H4AA	0.9700
O1A—C4A	1.419 (4)	C4A—H4AB	0.9700
O1A—H4	0.76 (3)	C4B—C2B	1.521 (5)
O2B—C5B	1.407 (4)	C4B—H4BA	0.9700
O2B—H3	0.84 (4)	C4B—H4BB	0.9700
C5B—C3B	1.497 (5)	C2B—C1B	1.499 (5)
C5B—H5BA	0.9700	C2B—H2BB	0.9800
C5B—H5BB	0.9700	C3A—C1A	1.478 (5)
O2A—C5A	1.425 (4)	C3A—C2A	1.509 (5)
O2A—H2	0.78 (4)	C3A—H3AA	0.9800
C5A—C3A	1.496 (5)	C1A—C2A	1.487 (5)
C5A—H5AA	0.9700	C2A—H2AB	0.9800
C4B—O1B—H1	108 (3)	C2B—C4B—H4BB	109.3
C4A—O1A—H4	108 (3)	H4BA—C4B—H4BB	108.0
C5B—O2B—H3	107 (3)	C1B—C2B—C3B	59.1 (2)
O2B—C5B—C3B	110.2 (3)	C1B—C2B—C4B	122.2 (3)
O2B—C5B—H5BA	109.6	C3B—C2B—C4B	121.0 (3)
C3B—C5B—H5BA	109.6	C1B—C2B—H2BB	114.5
O2B—C5B—H5BB	109.6	C3B—C2B—H2BB	114.5
C3B—C5B—H5BB	109.6	C4B—C2B—H2BB	114.5
H5BA—C5B—H5BB	108.1	C1A—C3A—C5A	122.3 (3)
C5A—O2A—H2	106 (3)	C1A—C3A—C2A	59.7 (2)
O2A—C5A—C3A	110.0 (3)	C5A—C3A—C2A	119.7 (3)
O2A—C5A—H5AA	109.7	C1A—C3A—H3AA	114.7
C3A—C5A—H5AA	109.7	C5A—C3A—H3AA	114.7
O2A—C5A—H5AB	109.7	C2A—C3A—H3AA	114.7
C3A—C5A—H5AB	109.7	C3A—C1A—C2A	61.2 (2)
H5AA—C5A—H5AB	108.2	C3A—C1A—Cl1A	119.9 (3)
C1B—C3B—C5B	122.8 (3)	C2A—C1A—Cl1A	121.1 (3)
C1B—C3B—C2B	59.9 (2)	C3A—C1A—Cl2A	118.0 (3)
C5B—C3B—C2B	121.3 (3)	C2A—C1A—Cl2A	117.6 (2)
C1B—C3B—H3BA	114.1	Cl1A—C1A—Cl2A	111.1 (2)
C5B—C3B—H3BA	114.1	C1A—C2A—C4A	122.6 (3)
C2B—C3B—H3BA	114.1	C1A—C2A—C3A	59.1 (2)
O1A—C4A—C2A	112.0 (3)	C4A—C2A—C3A	122.3 (3)
O1A—C4A—H4AA	109.2	C1A—C2A—H2AB	114.0
C2A—C4A—H4AA	109.2	C4A—C2A—H2AB	114.0
O1A—C4A—H4AB	109.2	C3A—C2A—H2AB	114.0
C2A—C4A—H4AB	109.2	C3B—C1B—C2B	61.0 (2)
H4AA—C4A—H4AB	107.9	C3B—C1B—Cl1B	119.1 (3)
O1B—C4B—C2B	111.6 (3)	C2B—C1B—Cl1B	121.1 (3)
O1B—C4B—H4BA	109.3	C3B—C1B—Cl2B	118.8 (3)
C2B—C4B—H4BA	109.3	C2B—C1B—Cl2B	117.8 (3)
O1B—C4B—H4BB	109.3	Cl1B—C1B—Cl2B	111.00 (18)
O2B—C5B—C3B—C1B	90.9 (4)	Cl1A—C1A—C2A—C3A	109.4 (3)
O2B—C5B—C3B—C2B	163.1 (3)	Cl2A—C1A—C2A—C3A	−108.5 (3)
C5B—C3B—C2B—C1B	−112.3 (4)	O1A—C4A—C2A—C1A	−103.1 (4)
C1B—C3B—C2B—C4B	111.4 (4)	O1A—C4A—C2A—C3A	−174.7 (3)
C5B—C3B—C2B—C4B	−0.9 (5)	C5A—C3A—C2A—C1A	−112.3 (4)
O1B—C4B—C2B—C1B	−100.3 (4)	C1A—C3A—C2A—C4A	111.5 (4)
O1B—C4B—C2B—C3B	−171.0 (3)	C5A—C3A—C2A—C4A	−0.8 (6)
O2A—C5A—C3A—C1A	93.8 (4)	C5B—C3B—C1B—C2B	110.0 (4)
O2A—C5A—C3A—C2A	164.8 (3)	C5B—C3B—C1B—Cl1B	−1.6 (5)
C5A—C3A—C1A—C2A	108.1 (4)	C2B—C3B—C1B—Cl1B	−111.6 (3)
C5A—C3A—C1A—Cl1A	−3.2 (5)	C5B—C3B—C1B—Cl2B	−142.3 (3)
C2A—C3A—C1A—Cl1A	−111.3 (3)	C2B—C3B—C1B—Cl2B	107.7 (3)
C5A—C3A—C1A—Cl2A	−144.1 (3)	C4B—C2B—C1B—C3B	−109.4 (4)
C2A—C3A—C1A—Cl2A	107.8 (3)	C3B—C2B—C1B—Cl1B	108.3 (3)
C3A—C1A—C2A—C4A	−110.8 (4)	C4B—C2B—C1B—Cl1B	−1.0 (5)
Cl1A—C1A—C2A—C4A	−1.4 (5)	C3B—C2B—C1B—Cl2B	−109.3 (3)
Cl2A—C1A—C2A—C4A	140.7 (3)	C4B—C2B—C1B—Cl2B	141.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H4···O2Bi	0.76 (3)	1.89 (3)	2.650 (4)	174 (4)
O2B—H3···O2Aii	0.84 (4)	1.84 (4)	2.668 (4)	171 (4)
O2A—H2···O1B	0.78 (4)	1.90 (4)	2.678 (4)	174 (4)
O1B—H1···O1Aiii	0.84 (4)	1.86 (4)	2.680 (5)	167 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H4⋯O2B i	0.76 (3)	1.89 (3)	2.650 (4)	174 (4)
O2B—H3⋯O2A ii	0.84 (4)	1.84 (4)	2.668 (4)	171 (4)
O2A—H2⋯O1B	0.78 (4)	1.90 (4)	2.678 (4)	174 (4)
O1B—H1⋯O1A iii	0.84 (4)	1.86 (4)	2.680 (5)	167 (4)

Symmetry codes: (i) ; (ii) ; (iii) .