2,6-Dichloro-phen-yl 4-chloro-benzoate.

In the title compound, C13H7Cl3O2, the dihedral angle between the benzene rings is 82.1 (2)°. The dihedral angle between the CO2 group and its carbon-bonded ring is 14.50 (19)° In the crystal, aromatic π-π stacking inter-actions [minimum ring centroid separation = 3.604 (2) Å] occur.

Related literature

For background to benzophenones, see: Khanum et al. (2004 ▶, 2009 ▶). For a related structure, see: Gowda et al. (2008 ▶).

Experimental

Crystal data

C13H7Cl3O2

M = 301.54

Triclinic,

a = 7.1584 (10) Å

b = 8.1183 (13) Å

c = 11.5338 (16) Å

α = 95.352 (11)°

β = 99.852 (10)°

γ = 105.854 (10)°

V = 628.30 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.72 mm−1

T = 103 K

0.32 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer

8510 measured reflections

2278 independent reflections

1738 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.158

S = 1.08

2278 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.84 e Å−3

Δρmin = −0.60 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: Mercury.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047204/hb6981sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047204/hb6981Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047204/hb6981Isup3.cml

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

C13H7Cl3O2	Z = 2
Mr = 301.54	F(000) = 304
Triclinic, P1	Dx = 1.594 Mg m−3
Hall symbol: -P 1	Melting point: 371 K
a = 7.1584 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1183 (13) Å	Cell parameters from 2278 reflections
c = 11.5338 (16) Å	θ = 1.8–26.0°
α = 95.352 (11)°	µ = 0.72 mm−1
β = 99.852 (10)°	T = 103 K
γ = 105.854 (10)°	Block, colourless
V = 628.30 (17) Å3	0.32 × 0.20 × 0.18 mm

Oxford Diffraction Xcalibur CCD diffractometer	1738 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 26.0°, θmin = 1.8°
Detector resolution: 16.0839 pixels mm-1	h = −8→8
ω scans	k = −10→10
8510 measured reflections	l = −14→14
2278 independent reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0961P)2 + 0.2256P] where P = (Fo2 + 2Fc2)/3
2278 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.84 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1	0.32525 (12)	−0.00436 (13)	0.72254 (8)	0.0296 (3)
Cl2	0.35105 (14)	−0.85956 (14)	0.44115 (9)	0.0354 (3)
Cl3	0.19259 (12)	−0.30913 (13)	1.10648 (8)	0.0322 (3)
O7	0.2686 (3)	−0.2891 (3)	0.8624 (2)	0.0248 (8)
O9	−0.0500 (3)	−0.3628 (4)	0.7612 (2)	0.0271 (8)
C1	0.2821 (5)	0.0096 (5)	0.8663 (3)	0.0248 (10)
C2	0.2782 (5)	0.1655 (5)	0.9231 (3)	0.0269 (11)
C3	0.2488 (5)	0.1744 (6)	1.0399 (3)	0.0289 (11)
C4	0.2242 (5)	0.0298 (5)	1.0965 (3)	0.0290 (13)
C5	0.2260 (4)	−0.1256 (5)	1.0378 (3)	0.0235 (10)
C6	0.2533 (4)	−0.1378 (5)	0.9200 (3)	0.0224 (10)
C8	0.1124 (5)	−0.3822 (5)	0.7724 (3)	0.0223 (10)
C10	0.1749 (5)	−0.5020 (5)	0.6946 (3)	0.0227 (10)
C11	0.3746 (5)	−0.4855 (5)	0.6964 (3)	0.0264 (11)
C12	0.4286 (5)	−0.5932 (5)	0.6183 (3)	0.0283 (11)
C13	0.2838 (5)	−0.7194 (5)	0.5378 (3)	0.0272 (11)
C14	0.0830 (5)	−0.7394 (5)	0.5340 (3)	0.0272 (11)
C15	0.0296 (5)	−0.6312 (5)	0.6119 (3)	0.0281 (11)
H2	0.29510	0.26470	0.88370	0.0320*
H3	0.24570	0.28060	1.08060	0.0350*
H4	0.20590	0.03730	1.17630	0.0350*
H11	0.47420	−0.39890	0.75230	0.0320*
H12	0.56480	−0.58090	0.61970	0.0340*
H14	−0.01560	−0.82690	0.47810	0.0330*
H15	−0.10690	−0.64390	0.61000	0.0340*

	U11	U22	U33	U12	U13	U23
Cl1	0.0248 (5)	0.0392 (6)	0.0206 (5)	0.0065 (4)	0.0017 (3)	−0.0027 (4)
Cl2	0.0410 (6)	0.0383 (7)	0.0287 (5)	0.0173 (4)	0.0097 (4)	−0.0077 (5)
Cl3	0.0255 (5)	0.0408 (7)	0.0250 (5)	0.0041 (4)	0.0029 (4)	−0.0004 (5)
O7	0.0182 (12)	0.0304 (16)	0.0218 (12)	0.0080 (10)	−0.0010 (9)	−0.0090 (12)
O9	0.0186 (12)	0.0338 (17)	0.0259 (13)	0.0086 (10)	0.0015 (10)	−0.0080 (13)
C1	0.0126 (16)	0.038 (2)	0.0202 (17)	0.0080 (14)	−0.0015 (13)	−0.0065 (17)
C2	0.0133 (16)	0.028 (2)	0.034 (2)	0.0049 (14)	−0.0012 (14)	−0.0074 (19)
C3	0.0155 (17)	0.034 (2)	0.030 (2)	0.0072 (14)	−0.0022 (14)	−0.0186 (18)
C4	0.0131 (16)	0.046 (3)	0.0215 (18)	0.0067 (15)	−0.0005 (13)	−0.0130 (19)
C5	0.0130 (16)	0.035 (2)	0.0175 (17)	0.0040 (14)	0.0001 (12)	−0.0064 (17)
C6	0.0125 (15)	0.030 (2)	0.0190 (17)	0.0049 (13)	−0.0020 (12)	−0.0112 (17)
C8	0.0175 (17)	0.025 (2)	0.0192 (17)	0.0012 (14)	0.0013 (13)	−0.0029 (16)
C10	0.0191 (17)	0.028 (2)	0.0186 (17)	0.0066 (14)	0.0022 (13)	−0.0046 (17)
C11	0.0200 (17)	0.030 (2)	0.0233 (18)	0.0033 (14)	0.0006 (14)	−0.0059 (17)
C12	0.0182 (17)	0.039 (2)	0.0259 (19)	0.0082 (15)	0.0051 (14)	−0.0045 (18)
C13	0.033 (2)	0.028 (2)	0.0235 (19)	0.0140 (16)	0.0087 (15)	−0.0016 (18)
C14	0.0249 (18)	0.029 (2)	0.0235 (19)	0.0070 (15)	−0.0008 (14)	−0.0038 (18)
C15	0.0173 (17)	0.032 (2)	0.029 (2)	0.0055 (15)	−0.0012 (14)	−0.0094 (19)

Cl1—C1	1.737 (4)	C10—C11	1.395 (5)
Cl2—C13	1.737 (4)	C10—C15	1.403 (5)
Cl3—C5	1.731 (4)	C11—C12	1.372 (5)
O7—C6	1.381 (4)	C12—C13	1.378 (5)
O7—C8	1.376 (4)	C13—C14	1.394 (5)
O9—C8	1.202 (4)	C14—C15	1.371 (5)
C1—C2	1.379 (5)	C2—H2	0.9500
C1—C6	1.380 (5)	C3—H3	0.9500
C2—C3	1.397 (5)	C4—H4	0.9500
C3—C4	1.380 (6)	C11—H11	0.9500
C4—C5	1.379 (5)	C12—H12	0.9500
C5—C6	1.404 (5)	C14—H14	0.9500
C8—C10	1.471 (5)	C15—H15	0.9500
C6—O7—C8	117.2 (3)	C11—C12—C13	119.5 (4)
Cl1—C1—C2	119.7 (3)	Cl2—C13—C12	119.8 (3)
Cl1—C1—C6	118.1 (3)	Cl2—C13—C14	119.1 (3)
C2—C1—C6	122.2 (3)	C12—C13—C14	121.2 (3)
C1—C2—C3	118.5 (4)	C13—C14—C15	119.1 (3)
C2—C3—C4	120.4 (4)	C10—C15—C14	120.5 (3)
C3—C4—C5	120.3 (3)	C1—C2—H2	121.00
Cl3—C5—C4	121.1 (3)	C3—C2—H2	121.00
Cl3—C5—C6	118.7 (3)	C2—C3—H3	120.00
C4—C5—C6	120.2 (3)	C4—C3—H3	120.00
O7—C6—C1	120.4 (3)	C3—C4—H4	120.00
O7—C6—C5	121.1 (3)	C5—C4—H4	120.00
C1—C6—C5	118.3 (3)	C10—C11—H11	120.00
O7—C8—O9	122.9 (3)	C12—C11—H11	120.00
O7—C8—C10	110.6 (3)	C11—C12—H12	120.00
O9—C8—C10	126.5 (3)	C13—C12—H12	120.00
C8—C10—C11	121.9 (3)	C13—C14—H14	120.00
C8—C10—C15	119.0 (3)	C15—C14—H14	120.00
C11—C10—C15	119.0 (3)	C10—C15—H15	120.00
C10—C11—C12	120.7 (3)	C14—C15—H15	120.00
C8—O7—C6—C1	−76.3 (4)	C4—C5—C6—O7	175.7 (3)
C8—O7—C6—C5	109.5 (4)	C4—C5—C6—C1	1.3 (5)
C6—O7—C8—O9	−18.4 (5)	O7—C8—C10—C11	−15.5 (5)
C6—O7—C8—C10	160.7 (3)	O7—C8—C10—C15	167.8 (3)
Cl1—C1—C2—C3	−178.2 (3)	O9—C8—C10—C11	163.6 (4)
C6—C1—C2—C3	1.6 (6)	O9—C8—C10—C15	−13.1 (6)
Cl1—C1—C6—O7	3.2 (5)	C8—C10—C11—C12	−176.4 (3)
Cl1—C1—C6—C5	177.6 (3)	C15—C10—C11—C12	0.3 (5)
C2—C1—C6—O7	−176.6 (3)	C8—C10—C15—C14	176.7 (3)
C2—C1—C6—C5	−2.2 (5)	C11—C10—C15—C14	−0.1 (6)
C1—C2—C3—C4	−0.1 (6)	C10—C11—C12—C13	−0.4 (6)
C2—C3—C4—C5	−0.8 (6)	C11—C12—C13—Cl2	−178.4 (3)
C3—C4—C5—Cl3	−179.3 (3)	C11—C12—C13—C14	0.2 (6)
C3—C4—C5—C6	0.1 (5)	Cl2—C13—C14—C15	178.7 (3)
Cl3—C5—C6—O7	−4.9 (4)	C12—C13—C14—C15	0.0 (6)
Cl3—C5—C6—C1	−179.3 (3)	C13—C14—C15—C10	−0.1 (6)