(2S)-1,1-Dichloro-2-(2-chloro-phen-yl)-2-(4-chloro-phen-yl)ethane.

The title compound, C(14)H(10)Cl(4), is easily crystallized while the other enanti-omorph only forms an oil upon crystallization attempts. The title compound has a considerably higher density, ρ ≃ 1.562 Mg m(-3) compared to the racemic substance, ρ ≃ 1.514 Mg m(-3). This is supported by the fact there are two inter-molecular halogen-halogen contacts in the title compound compared with only one the racemic compound. The dihedral angle between the two phenyl rings is 76.83 (5)°

Related literature

For related literature regarding the structure of the racemic compound, see: Arora & Bates (1976 ▶). For related literature on the toxicological effects, see: Allolio & Fassnacht (2006 ▶), Benecke et al. (1991 ▶), Bergenstal et al. (1960 ▶); Canti­llana et al. (2009 ▶).

Experimental

Crystal data

C14H10Cl4

M = 320.02

Monoclinic,

a = 6.13530 (10) Å

b = 12.0715 (2) Å

c = 9.4525 (2) Å

β = 103.5490 (18)°

V = 680.59 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.85 mm−1

T = 100 (2) K

0.34 × 0.24 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur-3 κ-diffractometer with Sapphire-III CCD

Absorption correction: gaussian (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.814, T max = 0.968

18569 measured reflections

4258 independent reflections

3935 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.060

S = 1.01

4258 reflections

164 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983 ▶), 1755 Friedel pairs

Flack parameter: 0.00 (4)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Bergerhoff, 1996 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶) and SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680804405X/bq2116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804405X/bq2116Isup2.hkl

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

C14H10Cl4	F(000) = 324
Mr = 320.02	Dx = 1.562 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 11963 reflections
a = 6.1353 (1) Å	θ = 3.8–32.1°
b = 12.0715 (2) Å	µ = 0.85 mm−1
c = 9.4525 (2) Å	T = 100 K
β = 103.5490 (18)°	Plate, colourless
V = 680.59 (2) Å3	0.34 × 0.24 × 0.04 mm
Z = 2

Oxford Diffraction Xcalibur-3 κ-diffractometer with Sapphire-III CCD	4258 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3935 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 16.54 pixels mm-1	θmax = 32.2°, θmin = 3.8°
ω scans at different φ	h = −9→9
Absorption correction: gaussian (CrysAlis RED; Oxford Diffraction, 2008)	k = −17→15
Tmin = 0.814, Tmax = 0.968	l = −13→14
18569 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026	w = 1/[σ2(Fo2) + (0.0358P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.060	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.40 e Å−3
4258 reflections	Δρmin = −0.31 e Å−3
164 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.009 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1755 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.00 (4)

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
C1	0.5723 (2)	0.58327 (13)	0.35281 (15)	0.0153 (3)
H1	0.4179	0.5513	0.3360	0.018*
C2	0.5682 (2)	0.70231 (12)	0.40708 (16)	0.0136 (3)
H2	0.7233	0.7330	0.4219	0.016*
Cl1	0.75951 (6)	0.50047 (3)	0.48348 (4)	0.02031 (8)
Cl2	0.66068 (6)	0.58092 (3)	0.18581 (4)	0.02172 (9)
C3	0.4118 (2)	0.77539 (12)	0.29597 (15)	0.0143 (3)
C4	0.4896 (3)	0.87540 (13)	0.25332 (16)	0.0178 (3)
H4	0.6434	0.8943	0.2871	0.021*
C5	0.3459 (3)	0.94815 (14)	0.16209 (16)	0.0196 (3)
H5	0.4006	1.0162	0.1335	0.024*
C6	0.1222 (3)	0.92006 (14)	0.11361 (15)	0.0174 (3)
C7	0.0412 (3)	0.81928 (14)	0.15077 (17)	0.0197 (3)
H7	−0.1116	0.7996	0.1141	0.024*
C8	0.1859 (2)	0.74824 (14)	0.24185 (17)	0.0185 (3)
H8	0.1310	0.6796	0.2683	0.022*
Cl3	−0.06289 (6)	1.01373 (3)	0.00690 (4)	0.02230 (9)
C9	0.5012 (2)	0.70772 (12)	0.55256 (16)	0.0149 (3)
C10	0.3199 (3)	0.64714 (13)	0.57858 (16)	0.0177 (3)
H10	0.2424	0.5974	0.5062	0.021*
C11	0.2503 (3)	0.65801 (14)	0.70765 (17)	0.0192 (3)
H11	0.1263	0.6162	0.7223	0.023*
C12	0.3609 (3)	0.72933 (15)	0.81459 (17)	0.0212 (3)
H12	0.3129	0.7366	0.9026	0.025*
C13	0.5417 (3)	0.79019 (14)	0.79373 (17)	0.0207 (3)
H13	0.6192	0.8389	0.8674	0.025*
C14	0.6088 (2)	0.77922 (13)	0.66334 (16)	0.0157 (3)
Cl4	0.83309 (6)	0.86142 (3)	0.64058 (4)	0.02012 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0144 (6)	0.0158 (7)	0.0172 (6)	0.0000 (5)	0.0071 (5)	−0.0006 (6)
C2	0.0121 (6)	0.0131 (7)	0.0159 (6)	−0.0025 (5)	0.0041 (5)	−0.0019 (5)
Cl1	0.01984 (16)	0.01761 (17)	0.02400 (17)	0.00417 (14)	0.00622 (12)	0.00057 (14)
Cl2	0.02671 (18)	0.02192 (19)	0.02051 (16)	−0.00424 (15)	0.01356 (14)	−0.00507 (14)
C3	0.0158 (6)	0.0140 (7)	0.0139 (6)	−0.0016 (5)	0.0054 (5)	−0.0012 (5)
C4	0.0171 (6)	0.0189 (8)	0.0175 (6)	−0.0054 (6)	0.0042 (5)	−0.0007 (6)
C5	0.0261 (8)	0.0167 (7)	0.0162 (7)	−0.0061 (6)	0.0054 (6)	0.0018 (5)
C6	0.0210 (7)	0.0189 (7)	0.0129 (6)	0.0025 (6)	0.0052 (5)	0.0020 (5)
C7	0.0173 (7)	0.0212 (8)	0.0202 (7)	−0.0024 (6)	0.0039 (6)	0.0019 (6)
C8	0.0171 (7)	0.0174 (7)	0.0206 (7)	−0.0043 (6)	0.0037 (5)	0.0021 (6)
Cl3	0.02784 (18)	0.02156 (19)	0.01717 (15)	0.00582 (15)	0.00459 (13)	0.00309 (14)
C9	0.0156 (6)	0.0138 (7)	0.0154 (6)	0.0041 (5)	0.0034 (5)	0.0005 (5)
C10	0.0205 (7)	0.0166 (7)	0.0172 (6)	0.0015 (6)	0.0070 (5)	0.0021 (6)
C11	0.0186 (7)	0.0203 (8)	0.0205 (7)	0.0034 (6)	0.0081 (6)	0.0048 (6)
C12	0.0263 (8)	0.0224 (8)	0.0163 (7)	0.0089 (7)	0.0077 (6)	0.0029 (6)
C13	0.0258 (8)	0.0189 (8)	0.0158 (7)	0.0070 (6)	0.0020 (6)	−0.0012 (6)
C14	0.0146 (6)	0.0126 (7)	0.0185 (6)	0.0029 (5)	0.0013 (5)	−0.0002 (5)
Cl4	0.01702 (16)	0.01679 (17)	0.02510 (18)	−0.00235 (13)	0.00201 (13)	−0.00440 (14)

C1—C2	1.528 (2)	C7—C8	1.381 (2)
C1—Cl1	1.7831 (15)	C7—H7	0.9500
C1—Cl2	1.7855 (14)	C8—H8	0.9500
C1—H1	1.0000	C9—C14	1.398 (2)
C2—C9	1.526 (2)	C9—C10	1.400 (2)
C2—C3	1.526 (2)	C10—C11	1.390 (2)
C2—H2	1.0000	C10—H10	0.9500
C3—C4	1.392 (2)	C11—C12	1.379 (2)
C3—C8	1.399 (2)	C11—H11	0.9500
C4—C5	1.391 (2)	C12—C13	1.382 (2)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.383 (2)	C13—C14	1.394 (2)
C5—H5	0.9500	C13—H13	0.9500
C6—C7	1.390 (2)	C14—Cl4	1.7503 (16)
C6—Cl3	1.7462 (16)
Cl1···Cl4i	3.4370 (5)	Cl2···Cl3ii	3.4888 (5)
C2—C1—Cl1	110.68 (10)	C8—C7—C6	119.01 (14)
C2—C1—Cl2	110.12 (10)	C8—C7—H7	120.5
Cl1—C1—Cl2	108.88 (8)	C6—C7—H7	120.5
C2—C1—H1	109.0	C7—C8—C3	121.31 (14)
Cl1—C1—H1	109.0	C7—C8—H8	119.3
Cl2—C1—H1	109.0	C3—C8—H8	119.3
C9—C2—C3	109.67 (11)	C14—C9—C10	116.49 (13)
C9—C2—C1	111.82 (12)	C14—C9—C2	121.46 (13)
C3—C2—C1	111.69 (12)	C10—C9—C2	121.92 (13)
C9—C2—H2	107.8	C11—C10—C9	121.65 (15)
C3—C2—H2	107.8	C11—C10—H10	119.2
C1—C2—H2	107.8	C9—C10—H10	119.2
C4—C3—C8	118.35 (14)	C12—C11—C10	120.19 (15)
C4—C3—C2	119.83 (13)	C12—C11—H11	119.9
C8—C3—C2	121.69 (13)	C10—C11—H11	119.9
C5—C4—C3	121.07 (14)	C11—C12—C13	120.04 (14)
C5—C4—H4	119.5	C11—C12—H12	120.0
C3—C4—H4	119.5	C13—C12—H12	120.0
C6—C5—C4	119.09 (15)	C12—C13—C14	119.25 (15)
C6—C5—H5	120.5	C12—C13—H13	120.4
C4—C5—H5	120.5	C14—C13—H13	120.4
C5—C6—C7	121.11 (15)	C13—C14—C9	122.37 (15)
C5—C6—Cl3	119.54 (13)	C13—C14—Cl4	117.29 (12)
C7—C6—Cl3	119.33 (12)	C9—C14—Cl4	120.33 (12)
Cl1—C1—C2—C9	−57.58 (13)	C2—C3—C8—C7	174.53 (14)
Cl2—C1—C2—C9	−178.02 (9)	C3—C2—C9—C14	−96.67 (15)
Cl1—C1—C2—C3	179.08 (9)	C1—C2—C9—C14	138.85 (14)
Cl2—C1—C2—C3	58.64 (13)	C3—C2—C9—C10	78.99 (17)
C9—C2—C3—C4	107.05 (15)	C1—C2—C9—C10	−45.48 (18)
C1—C2—C3—C4	−128.40 (14)	C14—C9—C10—C11	0.2 (2)
C9—C2—C3—C8	−68.77 (17)	C2—C9—C10—C11	−175.63 (14)
C1—C2—C3—C8	55.78 (18)	C9—C10—C11—C12	−0.3 (2)
C8—C3—C4—C5	1.6 (2)	C10—C11—C12—C13	−0.1 (2)
C2—C3—C4—C5	−174.36 (14)	C11—C12—C13—C14	0.6 (2)
C3—C4—C5—C6	0.1 (2)	C12—C13—C14—C9	−0.7 (2)
C4—C5—C6—C7	−2.1 (2)	C12—C13—C14—Cl4	178.08 (12)
C4—C5—C6—Cl3	176.66 (12)	C10—C9—C14—C13	0.3 (2)
C5—C6—C7—C8	2.3 (2)	C2—C9—C14—C13	176.15 (14)
Cl3—C6—C7—C8	−176.42 (12)	C10—C9—C14—Cl4	−178.44 (11)
C6—C7—C8—C3	−0.6 (2)	C2—C9—C14—Cl4	−2.55 (19)
C4—C3—C8—C7	−1.3 (2)

Table 1

Selected interatomic distances (Å)

Cl1⋯Cl4i	3.4370 (5)
Cl2⋯Cl3ii	3.4888 (5)

Symmetry codes: (i) ; (ii) .