2-Benzoyl-4-chloro-phenyl benzoate.

In the title compound, C20H13ClO3, the dihedral angles between the benzoate and the chloro-benzene and benzoyl rings are 68.82 (5) and 53.76 (6)°, respectively, while the dihedral angle between the benzoyl and benzoate rings is 81.17 (5)°. The eight atoms of the benzoyl residue are essentially planar with the exception of the O atom which lies 0.1860 (5) Å out of their mean plane (r.m.s. deviation = 0.97 Å). The nine atoms of benzoate residue are also essentially planar (r.m.s. deviation = 0.20 Å) with the ester O atom showing the greatest deviation [0.407 (12) Å] from their mean plane. In the crystal, mol-ecules are connected into centrosymmetric dimers by pairs of C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Sieroń et al. (2004 ▶); Mahendra et al. (2005 ▶); Naveen et al. (2006 ▶). For the biological activity of the title compound, see: Belluti et al. (2011 ▶); Revesz et al. (2004 ▶); Khanum et al. (2004 ▶, 2009 ▶, 2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H13ClO3

M = 336.75

Triclinic,

a = 9.1934 (2) Å

b = 9.8641 (3) Å

c = 10.0778 (3) Å

α = 94.033 (2)°

β = 114.207 (2)°

γ = 102.512 (2)°

V = 800.64 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.871, T max = 1.000

18813 measured reflections

3131 independent reflections

2631 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.084

S = 1.03

3131 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014396/go2090sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014396/go2090Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014396/go2090Isup3.cml

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

C20H13ClO3	Z = 2
Mr = 336.75	F(000) = 348
Triclinic, P1	Dx = 1.397 Mg m−3
Hall symbol: -P 1	Melting point: 367 K
a = 9.1934 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8641 (3) Å	Cell parameters from 10537 reflections
c = 10.0778 (3) Å	θ = 3.5–29.1°
α = 94.033 (2)°	µ = 0.25 mm−1
β = 114.207 (2)°	T = 293 K
γ = 102.512 (2)°	Block, white
V = 800.64 (4) Å3	0.30 × 0.20 × 0.20 mm

Oxford Xcalibur Sapphire3 diffractometer	3131 independent reflections
Radiation source: fine-focus sealed tube	2631 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −12→12
Tmin = 0.871, Tmax = 1.000	l = −12→12
18813 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0283P)2 + 0.3095P] where P = (Fo2 + 2Fc2)/3
3131 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.Elemental analysis for C20H13ClO3: IR (nujol): 1660 (C═O), 1750 cm-1 (ester, C═O); 1H NMR (CDCl3): δ 6.9–7.6 (m, 13H, Ar—H). Analysis, calculated for C20H13ClO3 (336.5): C 71.33, H 3.89, Cl 0.53; found: C 71.39, H 3.72, Cl 10.44%.

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
Cl1	0.13053 (5)	0.16990 (5)	0.62243 (6)	0.05937 (15)
O14	0.79582 (13)	0.43743 (11)	0.68298 (12)	0.0453 (3)
O15	0.94425 (14)	0.36025 (11)	0.88776 (12)	0.0459 (3)
C6	0.43806 (19)	0.16383 (16)	0.66293 (16)	0.0384 (3)
H6	0.4044	0.0682	0.6644	0.046*
C2	0.64376 (18)	0.36708 (16)	0.67781 (16)	0.0373 (3)
C1	0.59678 (18)	0.22283 (15)	0.67650 (16)	0.0357 (3)
C5	0.33045 (18)	0.24639 (17)	0.64737 (17)	0.0400 (4)
C7	0.70368 (18)	0.12708 (15)	0.67663 (17)	0.0385 (3)
C15	0.94012 (18)	0.43373 (15)	0.79760 (16)	0.0356 (3)
C16	1.08476 (18)	0.53267 (15)	0.79432 (17)	0.0355 (3)
O7	0.75790 (16)	0.12731 (13)	0.58523 (15)	0.0569 (3)
C8	0.73479 (18)	0.03063 (15)	0.78589 (17)	0.0376 (3)
C3	0.5371 (2)	0.44936 (16)	0.66627 (18)	0.0439 (4)
H3	0.5719	0.5459	0.6696	0.053*
C21	1.0687 (2)	0.61313 (17)	0.68447 (19)	0.0466 (4)
H21	0.9646	0.6049	0.6085	0.056*
C4	0.3790 (2)	0.38951 (17)	0.64981 (18)	0.0438 (4)
H4	0.3063	0.4447	0.6405	0.053*
C13	0.71872 (19)	0.05701 (16)	0.91536 (18)	0.0422 (4)
H13	0.6800	0.1331	0.9321	0.051*
C17	1.24005 (19)	0.54643 (16)	0.90776 (18)	0.0417 (4)
H17	1.2518	0.4925	0.9817	0.050*
C18	1.3775 (2)	0.64032 (18)	0.9110 (2)	0.0496 (4)
H18	1.4816	0.6503	0.9877	0.060*
C9	0.7918 (2)	−0.08432 (17)	0.7620 (2)	0.0481 (4)
H9	0.8034	−0.1032	0.6757	0.058*
C19	1.3604 (2)	0.71918 (18)	0.8006 (2)	0.0527 (4)
H19	1.4531	0.7818	0.8026	0.063*
C20	1.2068 (2)	0.70554 (19)	0.6876 (2)	0.0553 (5)
H20	1.1958	0.7586	0.6131	0.066*
C11	0.8161 (2)	−0.14242 (18)	0.9953 (2)	0.0539 (5)
H11	0.8441	−0.2001	1.0659	0.065*
C12	0.7599 (2)	−0.02918 (18)	1.0198 (2)	0.0505 (4)
H12	0.7495	−0.0105	1.1068	0.061*
C10	0.8310 (2)	−0.17028 (17)	0.8670 (2)	0.0551 (5)
H10	0.8678	−0.2476	0.8504	0.066*

	U11	U22	U33	U12	U13	U23
Cl1	0.0354 (2)	0.0713 (3)	0.0687 (3)	0.0086 (2)	0.0220 (2)	0.0177 (2)
O7	0.0698 (9)	0.0553 (7)	0.0646 (8)	0.0210 (6)	0.0445 (7)	0.0177 (6)
O14	0.0337 (6)	0.0453 (6)	0.0512 (7)	0.0043 (5)	0.0140 (5)	0.0220 (5)
O15	0.0434 (6)	0.0429 (6)	0.0474 (7)	0.0067 (5)	0.0168 (5)	0.0174 (5)
C1	0.0348 (8)	0.0362 (8)	0.0338 (8)	0.0081 (6)	0.0132 (6)	0.0089 (6)
C2	0.0327 (8)	0.0382 (8)	0.0366 (8)	0.0055 (6)	0.0121 (6)	0.0121 (6)
C3	0.0429 (9)	0.0341 (8)	0.0464 (9)	0.0090 (7)	0.0115 (7)	0.0107 (7)
C4	0.0402 (9)	0.0443 (9)	0.0437 (9)	0.0166 (7)	0.0127 (7)	0.0078 (7)
C5	0.0310 (8)	0.0484 (9)	0.0360 (8)	0.0073 (7)	0.0119 (7)	0.0074 (7)
C6	0.0385 (8)	0.0349 (8)	0.0375 (8)	0.0054 (6)	0.0143 (7)	0.0078 (6)
C7	0.0348 (8)	0.0343 (8)	0.0429 (9)	0.0039 (6)	0.0167 (7)	0.0043 (6)
C8	0.0308 (8)	0.0310 (7)	0.0463 (9)	0.0058 (6)	0.0137 (7)	0.0054 (6)
C9	0.0436 (9)	0.0396 (9)	0.0581 (11)	0.0116 (7)	0.0202 (8)	0.0032 (8)
C10	0.0467 (10)	0.0340 (8)	0.0779 (14)	0.0161 (8)	0.0182 (10)	0.0093 (8)
C11	0.0463 (10)	0.0418 (9)	0.0638 (12)	0.0107 (8)	0.0134 (9)	0.0201 (8)
C12	0.0515 (10)	0.0476 (10)	0.0500 (10)	0.0127 (8)	0.0192 (8)	0.0150 (8)
C13	0.0427 (9)	0.0345 (8)	0.0487 (9)	0.0116 (7)	0.0183 (8)	0.0082 (7)
C15	0.0375 (8)	0.0307 (7)	0.0375 (8)	0.0091 (6)	0.0152 (7)	0.0067 (6)
C16	0.0353 (8)	0.0313 (7)	0.0387 (8)	0.0071 (6)	0.0162 (7)	0.0049 (6)
C17	0.0409 (9)	0.0409 (8)	0.0403 (9)	0.0103 (7)	0.0153 (7)	0.0066 (7)
C18	0.0338 (9)	0.0498 (10)	0.0534 (10)	0.0048 (7)	0.0124 (8)	−0.0009 (8)
C19	0.0426 (10)	0.0439 (9)	0.0683 (12)	−0.0011 (7)	0.0281 (9)	0.0052 (8)
C20	0.0533 (11)	0.0502 (10)	0.0635 (12)	0.0068 (8)	0.0280 (10)	0.0241 (9)
C21	0.0389 (9)	0.0460 (9)	0.0497 (10)	0.0065 (7)	0.0156 (8)	0.0169 (8)

C1—C2	1.392 (2)	C11—C12	1.375 (2)
C1—C6	1.394 (2)	C11—H11	0.9300
C1—C7	1.503 (2)	C12—C13	1.383 (2)
C2—C3	1.378 (2)	C12—H12	0.9300
C2—O14	1.3977 (17)	C13—H13	0.9300
C3—C4	1.381 (2)	C15—O15	1.1952 (17)
C3—H3	0.9300	C15—O14	1.3660 (18)
C4—C5	1.380 (2)	C15—C16	1.483 (2)
C4—H4	0.9300	C16—C21	1.385 (2)
C5—C6	1.381 (2)	C16—C17	1.385 (2)
C5—Cl1	1.7333 (15)	C17—C18	1.382 (2)
C6—H6	0.9300	C17—H17	0.9300
C7—O7	1.2138 (19)	C18—C19	1.378 (3)
C7—C8	1.485 (2)	C18—H18	0.9300
C8—C13	1.385 (2)	C19—C20	1.373 (3)
C8—C9	1.393 (2)	C19—H19	0.9300
C9—C10	1.384 (2)	C20—C21	1.381 (2)
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.370 (3)	C21—H21	0.9300
C10—H10	0.9300
C2—C1—C6	117.95 (14)	C10—C11—H11	120.0
C2—C1—C7	122.98 (13)	C12—C11—H11	120.0
C6—C1—C7	118.88 (13)	C11—C12—C13	120.16 (17)
C3—C2—C1	121.19 (14)	C11—C12—H12	119.9
C3—C2—O14	115.25 (13)	C13—C12—H12	119.9
C1—C2—O14	123.49 (14)	C12—C13—C8	120.34 (15)
C2—C3—C4	120.46 (14)	C12—C13—H13	119.8
C2—C3—H3	119.8	C8—C13—H13	119.8
C4—C3—H3	119.8	O15—C15—O14	122.79 (13)
C5—C4—C3	118.93 (15)	O15—C15—C16	126.12 (14)
C5—C4—H4	120.5	O14—C15—C16	111.09 (12)
C3—C4—H4	120.5	C21—C16—C17	119.55 (14)
C4—C5—C6	120.98 (14)	C21—C16—C15	122.27 (14)
C4—C5—Cl1	119.15 (12)	C17—C16—C15	118.16 (13)
C6—C5—Cl1	119.87 (12)	C18—C17—C16	120.00 (15)
C5—C6—C1	120.46 (14)	C18—C17—H17	120.0
C5—C6—H6	119.8	C16—C17—H17	120.0
C1—C6—H6	119.8	C19—C18—C17	120.01 (16)
O7—C7—C8	121.80 (14)	C19—C18—H18	120.0
O7—C7—C1	119.47 (14)	C17—C18—H18	120.0
C8—C7—C1	118.69 (13)	C20—C19—C18	120.21 (15)
C13—C8—C9	119.11 (15)	C20—C19—H19	119.9
C13—C8—C7	121.70 (14)	C18—C19—H19	119.9
C9—C8—C7	119.07 (15)	C19—C20—C21	120.11 (16)
C10—C9—C8	119.83 (17)	C19—C20—H20	119.9
C10—C9—H9	120.1	C21—C20—H20	119.9
C8—C9—H9	120.1	C20—C21—C16	120.11 (15)
C11—C10—C9	120.57 (16)	C20—C21—H21	119.9
C11—C10—H10	119.7	C16—C21—H21	119.9
C9—C10—H10	119.7	C15—O14—C2	119.99 (11)
C10—C11—C12	119.99 (16)
C6—C1—C2—C3	0.1 (2)	C8—C9—C10—C11	−0.8 (3)
C7—C1—C2—C3	175.00 (14)	C9—C10—C11—C12	0.8 (3)
C6—C1—C2—O14	−176.52 (13)	C10—C11—C12—C13	−0.2 (3)
C7—C1—C2—O14	−1.6 (2)	C11—C12—C13—C8	−0.4 (3)
C1—C2—C3—C4	−1.4 (2)	C9—C8—C13—C12	0.5 (2)
O14—C2—C3—C4	175.44 (14)	C7—C8—C13—C12	−175.37 (15)
C2—C3—C4—C5	1.0 (2)	O15—C15—C16—C21	179.39 (16)
C3—C4—C5—C6	0.8 (2)	O14—C15—C16—C21	−1.5 (2)
C3—C4—C5—Cl1	−178.51 (13)	O15—C15—C16—C17	−2.2 (2)
C4—C5—C6—C1	−2.2 (2)	O14—C15—C16—C17	176.90 (13)
Cl1—C5—C6—C1	177.15 (12)	C21—C16—C17—C18	0.2 (2)
C2—C1—C6—C5	1.7 (2)	C15—C16—C17—C18	−178.25 (14)
C7—C1—C6—C5	−173.43 (14)	C16—C17—C18—C19	−0.7 (3)
C2—C1—C7—O7	−52.1 (2)	C17—C18—C19—C20	0.4 (3)
C6—C1—C7—O7	122.75 (17)	C18—C19—C20—C21	0.3 (3)
C2—C1—C7—C8	130.12 (15)	C19—C20—C21—C16	−0.8 (3)
C6—C1—C7—C8	−55.02 (19)	C17—C16—C21—C20	0.5 (3)
O7—C7—C8—C13	160.10 (16)	C15—C16—C21—C20	178.90 (16)
C1—C7—C8—C13	−22.2 (2)	O15—C15—O14—C2	8.1 (2)
O7—C7—C8—C9	−15.7 (2)	C16—C15—O14—C2	−171.02 (13)
C1—C7—C8—C9	161.98 (14)	C3—C2—O14—C15	124.88 (15)
C13—C8—C9—C10	0.1 (2)	C1—C2—O14—C15	−58.3 (2)
C7—C8—C9—C10	176.07 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O7i	0.93	2.50	3.394 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O7i	0.93	2.50	3.394 (2)	162

Symmetry code: (i) .