1,1,2,2-Tetra­chloro-1,2-diphenyl­ethane

The title compound, C₁₄H₁₀Cl₄, possesses C_i symmetry and crystallizes with one half-molecule in the asymmetric unit. The two phen­yl rings are antiperiplanar and inclined to one another by 180° by symmetry. The central C—C bond distance and the Cl—C—Cl bond angle [1.5887 (18) Å and 106.02 (7)°, respectively] are significantly different from ideal sp³ values. In the crystal, a supramolecular structure is achieved by soft parallel-displaced π–π stacking and C—H...π inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• R factor = 0.026
• wR factor = 0.067
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97 and WinGX2003 (Farrugia, 1999).

1,1,2,2-Tetrachloro-1,2-diphenylethane

Crystal data

C14H10Cl4	F(000) = 324
Mr = 320.02	Dx = 1.649 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 600 reflections
a = 8.5925 (10) Å	θ = 20–25°
b = 10.6129 (13) Å	µ = 0.89 mm^−1
c = 7.7558 (9) Å	T = 100 K
β = 114.315 (2)°	Block, colorless
V = 644.52 (13) Å^3	0.52 × 0.49 × 0.42 mm
Z = 2

Data collection

Bruker SMART area-detector diffractometer	Rint = 0.021
Graphite monochromator	θmax = 27.6°, θmin = 2.6°
φ and ω scans	h = −10→10
6982 measured reflections	k = −13→13
1461 independent reflections	l = −10→10
1451 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0354P)^2 + 0.3344P] where P = (Fo^2 + 2Fc^2)/3
1461 reflections	(Δ/σ)max = 0.001
82 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.46504 (4)	0.00002 (3)	0.20693 (4)	0.0158 (1)
Cl2	0.57707 (4)	0.19318 (3)	0.48969 (4)	0.0160 (1)
C1	0.45328 (16)	0.05183 (12)	0.42181 (17)	0.0128 (3)
C2	0.26869 (16)	0.07810 (12)	0.38812 (18)	0.0140 (3)
C3	0.22964 (18)	0.17374 (13)	0.48755 (19)	0.0167 (3)
C4	0.06136 (18)	0.19511 (13)	0.4596 (2)	0.0191 (4)
C5	−0.06910 (17)	0.12216 (14)	0.3324 (2)	0.0194 (4)
C6	−0.03112 (17)	0.02648 (14)	0.2344 (2)	0.0179 (4)
C7	0.13693 (18)	0.00440 (12)	0.2613 (2)	0.0160 (4)
H3	0.31844	0.22437	0.57459	0.0201*
H4	0.03568	0.26006	0.52813	0.0229*
H5	−0.18417	0.13766	0.31249	0.0233*
H6	−0.12033	−0.02432	0.14832	0.0215*
H7	0.16197	−0.06108	0.19317	0.0192*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0167 (2)	0.0189 (2)	0.0124 (2)	0.0015 (1)	0.0066 (1)	−0.0004 (1)
Cl2	0.0154 (2)	0.0118 (2)	0.0200 (2)	−0.0018 (1)	0.0066 (1)	0.0000 (1)
C1	0.0147 (6)	0.0119 (6)	0.0117 (6)	−0.0010 (5)	0.0053 (5)	−0.0012 (4)
C2	0.0133 (6)	0.0141 (6)	0.0139 (6)	0.0016 (5)	0.0049 (5)	0.0028 (5)
C3	0.0173 (6)	0.0153 (6)	0.0168 (6)	0.0017 (5)	0.0064 (5)	0.0006 (5)
C4	0.0201 (7)	0.0191 (7)	0.0203 (7)	0.0058 (5)	0.0105 (5)	0.0031 (5)
C5	0.0151 (6)	0.0239 (7)	0.0202 (7)	0.0049 (5)	0.0083 (5)	0.0086 (5)
C6	0.0139 (7)	0.0221 (7)	0.0149 (6)	−0.0012 (5)	0.0031 (5)	0.0039 (5)
C7	0.0167 (7)	0.0161 (6)	0.0139 (6)	0.0005 (5)	0.0051 (5)	0.0005 (4)

Geometric parameters (Å, º)

Cl1—C1	1.7969 (13)	C5—C6	1.385 (2)
Cl2—C1	1.7882 (14)	C6—C7	1.391 (2)
C1—C2	1.523 (2)	C3—H3	0.95
C1—C1^i	1.5887 (18)	C4—H4	0.95
C2—C3	1.397 (2)	C5—H5	0.95
C2—C7	1.394 (2)	C6—H6	0.95
C3—C4	1.390 (2)	C7—H7	0.95
C4—C5	1.385 (2)
Cl1···Cl1^ii	3.5003 (6)	C6···C4^viii	3.426 (2)
Cl1···Cl2^i	3.2516 (6)	C6···C5^viii	3.484 (2)
Cl1···Cl2^iii	3.5506 (6)	C6···C7^vi	3.583 (2)
Cl1···C3^i	3.2831 (15)	C7···C6^vi	3.583 (2)
Cl2···C7^i	3.2027 (15)	C7···Cl2^i	3.2027 (15)
Cl2···Cl1^iv	3.5506 (6)	C6···H4^ix	2.9626
Cl2···Cl1^i	3.2516 (6)	C6···H7^vi	3.0538
Cl1···H5^v	3.1396	C7···H4^ix	2.9967
Cl1···H7	2.6428	H3···Cl2	2.5859
Cl1···H3^i	3.0672	H3···Cl1^i	3.0672
Cl1···H6^vi	3.1161	H4···C6^x	2.9626
Cl2···H3	2.5859	H4···C7^x	2.9967
Cl2···H5^v	2.9609	H5···Cl1^xi	3.1396
Cl2···H7^i	2.9157	H5···Cl2^xi	2.9609
Cl2···H5^vii	3.0773	H5···Cl2^xii	3.0773
C3···Cl1^i	3.2831 (15)	H6···Cl1^vi	3.1161
C4···C6^viii	3.426 (2)	H7···Cl1	2.6428
C5···C5^viii	3.514 (2)	H7···Cl2^i	2.9157
C5···C6^viii	3.484 (2)	H7···C6^vi	3.0538
Cl1—C1—Cl2	106.02 (7)	C5—C6—C7	120.37 (14)
Cl1—C1—C2	110.43 (9)	C2—C7—C6	120.16 (13)
Cl1—C1—C1^i	107.00 (9)	C2—C3—H3	119.88
Cl2—C1—C2	110.37 (9)	C4—C3—H3	119.88
Cl2—C1—C1^i	107.69 (9)	C3—C4—H4	119.83
C1^i—C1—C2	114.89 (11)	C5—C4—H4	119.84
C1—C2—C3	120.54 (12)	C4—C5—H5	120.12
C1—C2—C7	120.27 (12)	C6—C5—H5	120.14
C3—C2—C7	119.16 (14)	C5—C6—H6	119.82
C2—C3—C4	120.24 (13)	C7—C6—H6	119.81
C3—C4—C5	120.32 (13)	C2—C7—H7	119.92
C4—C5—C6	119.74 (15)	C6—C7—H7	119.92
Cl1—C1—C2—C3	−146.78 (11)	C2—C1—C1^i—Cl1^i	−57.02 (12)
Cl1—C1—C2—C7	35.06 (15)	C2—C1—C1^i—Cl2^i	56.59 (12)
Cl2—C1—C2—C3	−29.87 (15)	C2—C1—C1^i—C2^i	180.00 (11)
Cl2—C1—C2—C7	151.96 (11)	C1—C2—C3—C4	−178.38 (12)
C1^i—C1—C2—C3	92.10 (15)	C7—C2—C3—C4	−0.2 (2)
C1^i—C1—C2—C7	−86.07 (15)	C1—C2—C7—C6	178.34 (12)
Cl1—C1—C1^i—Cl1^i	−180.00 (8)	C3—C2—C7—C6	0.1 (2)
Cl1—C1—C1^i—Cl2^i	−66.40 (10)	C2—C3—C4—C5	−0.3 (2)
Cl1—C1—C1^i—C2^i	57.02 (12)	C3—C4—C5—C6	0.8 (2)
Cl2—C1—C1^i—Cl1^i	66.40 (10)	C4—C5—C6—C7	−0.8 (2)
Cl2—C1—C1^i—Cl2^i	179.98 (10)	C5—C6—C7—C2	0.4 (2)
Cl2—C1—C1^i—C2^i	−56.59 (12)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) x+1, y, z; (vi) −x, −y, −z; (vii) x+1, −y+1/2, z+1/2; (viii) −x, −y, −z+1; (ix) x, −y+1/2, z−1/2; (x) x, −y+1/2, z+1/2; (xi) x−1, y, z; (xii) x−1, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl2	0.95	2.59	2.9856 (17)	106
C7—H7···Cl1	0.95	2.64	3.0178 (17)	104