4-Chloro-2-(2-chloro-benzoyl)phenol.

In the title mol-ecule, C13H8Cl2O2, the dihedral angle between the benzene rings is 74.53 (9)°. An intra-molecular O-H⋯O hydrogen bond leading to a S(6) ring is observed. In the crystal, the mol-ecules are connected into a three-dimensional network by C-H⋯O and π-π [inter-centroid distance = 3.6254 (10) Å] inter-actions.

Related literature

For the biological activity of benzo­phenone derivatives, see: Khanum et al. (2005 ▶, 2010 ▶). For a related structure, see: Devaiah et al. (2006 ▶).

Experimental

Crystal data

C13H8Cl2O2

M = 267.09

Orthorhombic,

a = 16.0231 (4) Å

b = 7.4216 (2) Å

c = 19.6843 (5) Å

V = 2340.80 (10) Å3

Z = 8

Cu Kα radiation

μ = 4.87 mm−1

T = 295 K

0.20 × 0.19 × 0.18 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.442, T max = 0.474

15868 measured reflections

1972 independent reflections

1712 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.06

1972 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; 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: Mercury.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813025609/tk5253sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025609/tk5253Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025609/tk5253Isup3.cml

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

C13H8Cl2O2	F(000) = 1088
Mr = 267.09	Dx = 1.516 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1972 reflections
a = 16.0231 (4) Å	θ = 4.5–64.9°
b = 7.4216 (2) Å	µ = 4.87 mm−1
c = 19.6843 (5) Å	T = 295 K
V = 2340.80 (10) Å3	Needle, yellow
Z = 8	0.20 × 0.19 × 0.18 mm

Bruker X8 Proteum diffractometer	1972 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1712 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.062
Detector resolution: 10.7 pixels mm-1	θmax = 64.9°, θmin = 4.5°
\φ and \ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −8→4
Tmin = 0.442, Tmax = 0.474	l = −23→22
15868 measured 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0717P)2 + 0.4839P] where P = (Fo2 + 2Fc2)/3
1972 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.21 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
Cl7	0.41862 (4)	0.46830 (6)	0.29403 (2)	0.0481 (2)
Cl17	0.68664 (3)	0.11456 (7)	0.40130 (3)	0.0439 (2)
O9	0.29828 (9)	0.2266 (2)	0.43513 (7)	0.0486 (5)
O16	0.38062 (10)	0.3221 (2)	0.54298 (7)	0.0428 (5)
C1	0.37955 (13)	0.1912 (2)	0.21207 (9)	0.0330 (5)
C2	0.35120 (13)	0.0191 (2)	0.19888 (9)	0.0341 (5)
C3	0.32654 (14)	−0.0927 (2)	0.25143 (10)	0.0376 (6)
C4	0.33080 (13)	−0.0318 (2)	0.31807 (9)	0.0356 (6)
C5	0.36117 (12)	0.1391 (2)	0.33254 (9)	0.0289 (5)
C6	0.38485 (12)	0.2493 (2)	0.27869 (9)	0.0296 (5)
C8	0.36471 (13)	0.1988 (2)	0.40532 (9)	0.0317 (5)
C10	0.44516 (12)	0.2149 (2)	0.43988 (9)	0.0288 (5)
C11	0.44873 (12)	0.2764 (2)	0.50758 (9)	0.0310 (5)
C12	0.52597 (14)	0.2929 (2)	0.53977 (9)	0.0390 (6)
C13	0.59771 (13)	0.2463 (3)	0.50739 (10)	0.0373 (5)
C14	0.59454 (12)	0.1799 (2)	0.44109 (10)	0.0324 (5)
C15	0.52003 (12)	0.1657 (2)	0.40762 (9)	0.0289 (5)
H1	0.39490	0.26710	0.17660	0.0400*
H2	0.34870	−0.02210	0.15430	0.0410*
H3	0.30720	−0.20820	0.24220	0.0450*
H4	0.31320	−0.10620	0.35330	0.0430*
H12	0.52840	0.33640	0.58400	0.0470*
H13	0.64880	0.25860	0.52940	0.0450*
H15	0.51890	0.12320	0.36320	0.0350*
H16	0.33910	0.30760	0.51930	0.0640*

	U11	U22	U33	U12	U13	U23
Cl7	0.0670 (4)	0.0413 (3)	0.0359 (3)	−0.0138 (2)	−0.0087 (2)	0.0009 (2)
Cl17	0.0269 (3)	0.0563 (3)	0.0484 (3)	0.0061 (2)	−0.0024 (2)	0.0039 (2)
O9	0.0283 (8)	0.0882 (10)	0.0294 (7)	0.0028 (7)	0.0032 (7)	−0.0086 (7)
O16	0.0401 (9)	0.0647 (8)	0.0237 (7)	−0.0061 (7)	0.0043 (6)	−0.0069 (6)
C1	0.0312 (10)	0.0440 (9)	0.0239 (9)	0.0027 (8)	−0.0001 (8)	0.0026 (7)
C2	0.0311 (10)	0.0465 (9)	0.0247 (9)	0.0068 (8)	−0.0053 (8)	−0.0055 (7)
C3	0.0368 (11)	0.0413 (9)	0.0347 (10)	−0.0027 (8)	−0.0084 (10)	−0.0037 (7)
C4	0.0332 (10)	0.0454 (10)	0.0281 (9)	−0.0050 (8)	−0.0019 (9)	0.0052 (7)
C5	0.0208 (9)	0.0437 (8)	0.0222 (8)	0.0011 (7)	−0.0026 (8)	0.0000 (6)
C6	0.0264 (9)	0.0381 (8)	0.0244 (8)	0.0004 (7)	−0.0020 (8)	−0.0006 (7)
C8	0.0262 (10)	0.0449 (9)	0.0241 (9)	0.0002 (7)	0.0020 (8)	0.0012 (7)
C10	0.0295 (10)	0.0349 (8)	0.0220 (8)	−0.0020 (7)	−0.0023 (8)	0.0030 (6)
C11	0.0331 (11)	0.0382 (8)	0.0216 (8)	−0.0044 (7)	0.0024 (8)	0.0022 (6)
C12	0.0465 (13)	0.0476 (9)	0.0228 (9)	−0.0109 (9)	−0.0073 (9)	0.0013 (7)
C13	0.0336 (10)	0.0475 (9)	0.0307 (9)	−0.0070 (8)	−0.0104 (9)	0.0074 (7)
C14	0.0291 (10)	0.0359 (8)	0.0322 (9)	−0.0006 (7)	−0.0036 (9)	0.0066 (7)
C15	0.0291 (10)	0.0353 (8)	0.0224 (8)	0.0005 (7)	−0.0009 (8)	0.0013 (6)

Cl7—C6	1.7394 (16)	C10—C15	1.406 (3)
Cl17—C14	1.740 (2)	C10—C11	1.410 (2)
O9—C8	1.233 (2)	C11—C12	1.396 (3)
O16—C11	1.339 (2)	C12—C13	1.359 (3)
O16—H16	0.8200	C13—C14	1.396 (3)
C1—C6	1.383 (2)	C14—C15	1.368 (3)
C1—C2	1.380 (2)	C1—H1	0.9300
C2—C3	1.384 (3)	C2—H2	0.9300
C3—C4	1.389 (3)	C3—H3	0.9300
C4—C5	1.388 (2)	C4—H4	0.9300
C5—C6	1.392 (2)	C12—H12	0.9300
C5—C8	1.501 (2)	C13—H13	0.9300
C8—C10	1.462 (3)	C15—H15	0.9300
C11—O16—H16	109.00	C11—C12—C13	120.98 (17)
C2—C1—C6	119.15 (16)	C12—C13—C14	119.83 (19)
C1—C2—C3	120.55 (16)	Cl17—C14—C13	119.24 (15)
C2—C3—C4	119.79 (15)	C13—C14—C15	120.62 (18)
C3—C4—C5	120.55 (16)	Cl17—C14—C15	120.14 (15)
C4—C5—C8	118.62 (15)	C10—C15—C14	120.49 (17)
C6—C5—C8	122.91 (14)	C2—C1—H1	120.00
C4—C5—C6	118.45 (16)	C6—C1—H1	120.00
Cl7—C6—C5	120.12 (13)	C1—C2—H2	120.00
C1—C6—C5	121.49 (15)	C3—C2—H2	120.00
Cl7—C6—C1	118.36 (13)	C2—C3—H3	120.00
O9—C8—C10	121.73 (16)	C4—C3—H3	120.00
C5—C8—C10	120.10 (17)	C3—C4—H4	120.00
O9—C8—C5	118.11 (18)	C5—C4—H4	120.00
C8—C10—C11	120.13 (17)	C11—C12—H12	120.00
C8—C10—C15	121.39 (16)	C13—C12—H12	119.00
C11—C10—C15	118.46 (17)	C12—C13—H13	120.00
O16—C11—C10	122.76 (17)	C14—C13—H13	120.00
O16—C11—C12	117.67 (16)	C10—C15—H15	120.00
C10—C11—C12	119.57 (17)	C14—C15—H15	120.00
C6—C1—C2—C3	1.5 (3)	O9—C8—C10—C15	173.55 (16)
C2—C1—C6—Cl7	−178.65 (16)	C5—C8—C10—C11	178.00 (14)
C2—C1—C6—C5	−0.9 (3)	C5—C8—C10—C15	−3.7 (2)
C1—C2—C3—C4	−0.4 (3)	C8—C10—C11—O16	0.0 (2)
C2—C3—C4—C5	−1.3 (3)	C8—C10—C11—C12	−179.36 (14)
C3—C4—C5—C6	1.8 (3)	C15—C10—C11—O16	−178.36 (15)
C3—C4—C5—C8	−179.90 (19)	C15—C10—C11—C12	2.3 (2)
C4—C5—C6—Cl7	176.96 (15)	C8—C10—C15—C14	−179.27 (15)
C4—C5—C6—C1	−0.7 (3)	C11—C10—C15—C14	−0.9 (2)
C8—C5—C6—Cl7	−1.2 (3)	O16—C11—C12—C13	178.94 (17)
C8—C5—C6—C1	−178.93 (18)	C10—C11—C12—C13	−1.7 (2)
C4—C5—C8—O9	−69.0 (2)	C11—C12—C13—C14	−0.4 (3)
C4—C5—C8—C10	108.3 (2)	C12—C13—C14—Cl17	−178.09 (14)
C6—C5—C8—O9	109.2 (2)	C12—C13—C14—C15	1.8 (3)
C6—C5—C8—C10	−73.5 (2)	Cl17—C14—C15—C10	178.75 (12)
O9—C8—C10—C11	−4.8 (2)	C13—C14—C15—C10	−1.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O16—H16···O9	0.82	1.88	2.598 (2)	146
C13—H13···O9i	0.93	2.50	3.413 (3)	168
C6—Cl7···Cg1ii	1.74 (1)	3.89 (1)	4.901 (2)	116 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O16—H16⋯O9	0.82	1.88	2.598 (2)	146
C13—H13⋯O9i	0.93	2.50	3.413 (3)	168

Symmetry code: (i) .