2,4-Dichloro-benzyl 2-meth-oxy-benzoate.

In the title compound, C15H12Cl2O3, the aromatic rings make a dihedral angle of 10.78 (4)°. In the molecule, there is a short C-H⋯O contact. In the crystal, C-H⋯O contacts connect the mol-ecules into C(7)C(8) chains along the b axis. The shortest inter-centroid distance between two benzoic acid aromatic systems is 3.7416 (8) Å.

Related literature

For pharmacological properties of phenyl benzoates, see: Oxford et al. (2005 ▶); Ostergaard (1994 ▶). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C15H12Cl2O3

M = 311.15

Monoclinic,

a = 12.1816 (5) Å

b = 15.2481 (6) Å

c = 7.4207 (4) Å

β = 99.299 (2)°

V = 1360.25 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 200 K

0.38 × 0.37 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.847, T max = 0.982

12933 measured reflections

3379 independent reflections

2868 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.03

3379 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006156/ng5318sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006156/ng5318Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006156/ng5318Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006156/ng5318Isup4.cml

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

C15H12Cl2O3	F(000) = 640
Mr = 311.15	Dx = 1.519 Mg m−3
Monoclinic, P21/c	Melting point = 376–374 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.1816 (5) Å	Cell parameters from 6565 reflections
b = 15.2481 (6) Å	θ = 2.7–28.3°
c = 7.4207 (4) Å	µ = 0.48 mm−1
β = 99.299 (2)°	T = 200 K
V = 1360.25 (11) Å3	Block, colourless
Z = 4	0.38 × 0.37 × 0.15 mm

Bruker APEXII CCD diffractometer	3379 independent reflections
Radiation source: fine-focus sealed tube	2868 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
φ and ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
Tmin = 0.847, Tmax = 0.982	k = −20→20
12933 measured reflections	l = −9→9

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0407P)2 + 0.3593P] where P = (Fo2 + 2Fc2)/3
3379 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.83729 (2)	0.13621 (2)	0.22173 (5)	0.03453 (10)
Cl2	0.93726 (3)	0.47791 (2)	0.20393 (6)	0.05086 (12)
O1	0.50796 (7)	0.23368 (5)	0.32072 (13)	0.0302 (2)
O2	0.42680 (8)	0.10301 (6)	0.32410 (15)	0.0417 (2)
O3	0.39479 (7)	0.37220 (5)	0.34997 (14)	0.0354 (2)
C1	0.60253 (9)	0.19251 (7)	0.26253 (17)	0.0260 (2)
H1A	0.5802	0.1629	0.1435	0.031*
H1B	0.6354	0.1483	0.3532	0.031*
C2	0.42351 (9)	0.18141 (7)	0.34359 (16)	0.0250 (2)
C3	0.37406 (13)	0.46402 (9)	0.3289 (2)	0.0465 (4)
H3A	0.4363	0.4920	0.2823	0.070*
H3B	0.3664	0.4896	0.4473	0.070*
H3C	0.3053	0.4735	0.2425	0.070*
C11	0.68490 (9)	0.26426 (7)	0.24577 (15)	0.0234 (2)
C12	0.79427 (9)	0.24488 (7)	0.22730 (16)	0.0244 (2)
C13	0.87222 (10)	0.30935 (8)	0.21331 (17)	0.0291 (3)
H13	0.9464	0.2945	0.2012	0.035*
C14	0.83948 (10)	0.39622 (8)	0.21735 (17)	0.0303 (3)
C15	0.73151 (10)	0.41879 (8)	0.23178 (18)	0.0306 (3)
H15	0.7097	0.4786	0.2319	0.037*
C16	0.65539 (10)	0.35254 (8)	0.24611 (17)	0.0274 (2)
H16	0.5810	0.3678	0.2564	0.033*
C21	0.32638 (9)	0.22915 (7)	0.39497 (16)	0.0249 (2)
C22	0.31284 (9)	0.32091 (8)	0.39762 (16)	0.0268 (2)
C23	0.21596 (10)	0.35594 (9)	0.44706 (18)	0.0327 (3)
H23	0.2066	0.4177	0.4505	0.039*
C24	0.13359 (10)	0.30135 (10)	0.49094 (18)	0.0355 (3)
H24	0.0686	0.3260	0.5261	0.043*
C25	0.14469 (10)	0.21127 (10)	0.48428 (18)	0.0351 (3)
H25	0.0870	0.1740	0.5113	0.042*
C26	0.24091 (10)	0.17634 (8)	0.43777 (17)	0.0296 (3)
H26	0.2491	0.1144	0.4349	0.036*

	U11	U22	U33	U12	U13	U23
Cl1	0.02915 (16)	0.02768 (16)	0.0483 (2)	0.00585 (11)	0.01086 (13)	−0.00228 (12)
Cl2	0.03554 (19)	0.03606 (19)	0.0846 (3)	−0.00991 (14)	0.02065 (18)	0.00427 (17)
O1	0.0219 (4)	0.0242 (4)	0.0472 (5)	−0.0005 (3)	0.0138 (4)	−0.0033 (3)
O2	0.0334 (5)	0.0234 (4)	0.0723 (7)	−0.0010 (4)	0.0204 (5)	−0.0008 (4)
O3	0.0301 (4)	0.0218 (4)	0.0571 (6)	0.0015 (3)	0.0155 (4)	0.0014 (4)
C1	0.0220 (5)	0.0230 (5)	0.0345 (6)	0.0021 (4)	0.0090 (4)	−0.0009 (5)
C2	0.0220 (5)	0.0251 (5)	0.0280 (6)	−0.0011 (4)	0.0040 (4)	0.0020 (4)
C3	0.0460 (8)	0.0234 (6)	0.0740 (11)	0.0030 (6)	0.0218 (8)	0.0014 (6)
C11	0.0219 (5)	0.0261 (5)	0.0227 (5)	0.0005 (4)	0.0048 (4)	0.0003 (4)
C12	0.0244 (5)	0.0259 (5)	0.0235 (5)	0.0033 (4)	0.0052 (4)	−0.0005 (4)
C13	0.0218 (5)	0.0350 (6)	0.0318 (6)	0.0008 (5)	0.0086 (4)	0.0001 (5)
C14	0.0282 (6)	0.0295 (6)	0.0347 (6)	−0.0058 (5)	0.0092 (5)	0.0012 (5)
C15	0.0311 (6)	0.0252 (6)	0.0372 (7)	0.0006 (5)	0.0102 (5)	0.0013 (5)
C16	0.0231 (5)	0.0276 (6)	0.0329 (6)	0.0023 (4)	0.0085 (5)	0.0009 (5)
C21	0.0220 (5)	0.0277 (6)	0.0250 (6)	0.0003 (4)	0.0036 (4)	−0.0007 (4)
C22	0.0224 (5)	0.0291 (6)	0.0290 (6)	0.0003 (4)	0.0044 (4)	−0.0006 (5)
C23	0.0274 (6)	0.0362 (7)	0.0346 (7)	0.0064 (5)	0.0053 (5)	−0.0045 (5)
C24	0.0238 (6)	0.0517 (8)	0.0318 (6)	0.0049 (5)	0.0068 (5)	−0.0059 (6)
C25	0.0245 (6)	0.0493 (8)	0.0328 (7)	−0.0062 (5)	0.0089 (5)	−0.0022 (6)
C26	0.0271 (6)	0.0330 (6)	0.0293 (6)	−0.0041 (5)	0.0063 (5)	−0.0003 (5)

Cl1—C12	1.7403 (12)	C13—C14	1.3849 (17)
Cl2—C14	1.7374 (12)	C13—H13	0.9500
O1—C2	1.3337 (13)	C14—C15	1.3804 (17)
O1—C1	1.4383 (13)	C15—C16	1.3869 (17)
O2—C2	1.2057 (15)	C15—H15	0.9500
O3—C22	1.3592 (14)	C16—H16	0.9500
O3—C3	1.4267 (15)	C21—C26	1.3929 (16)
C1—C11	1.5033 (15)	C21—C22	1.4093 (16)
C1—H1A	0.9900	C22—C23	1.3973 (16)
C1—H1B	0.9900	C23—C24	1.3826 (19)
C2—C21	1.4902 (16)	C23—H23	0.9500
C3—H3A	0.9800	C24—C25	1.382 (2)
C3—H3B	0.9800	C24—H24	0.9500
C3—H3C	0.9800	C25—C26	1.3811 (17)
C11—C12	1.3929 (16)	C25—H25	0.9500
C11—C16	1.3933 (16)	C26—H26	0.9500
C12—C13	1.3823 (17)
C2—O1—C1	116.68 (9)	C15—C14—Cl2	119.76 (10)
C22—O3—C3	117.96 (10)	C13—C14—Cl2	118.81 (9)
O1—C1—C11	106.55 (9)	C14—C15—C16	118.79 (11)
O1—C1—H1A	110.4	C14—C15—H15	120.6
C11—C1—H1A	110.4	C16—C15—H15	120.6
O1—C1—H1B	110.4	C15—C16—C11	121.85 (11)
C11—C1—H1B	110.4	C15—C16—H16	119.1
H1A—C1—H1B	108.6	C11—C16—H16	119.1
O2—C2—O1	122.41 (11)	C26—C21—C22	118.51 (11)
O2—C2—C21	123.93 (11)	C26—C21—C2	115.44 (10)
O1—C2—C21	113.66 (10)	C22—C21—C2	126.02 (10)
O3—C3—H3A	109.5	O3—C22—C23	122.36 (11)
O3—C3—H3B	109.5	O3—C22—C21	118.37 (10)
H3A—C3—H3B	109.5	C23—C22—C21	119.27 (11)
O3—C3—H3C	109.5	C24—C23—C22	120.50 (12)
H3A—C3—H3C	109.5	C24—C23—H23	119.8
H3B—C3—H3C	109.5	C22—C23—H23	119.8
C12—C11—C16	117.15 (11)	C25—C24—C23	120.74 (12)
C12—C11—C1	121.04 (10)	C25—C24—H24	119.6
C16—C11—C1	121.81 (10)	C23—C24—H24	119.6
C13—C12—C11	122.41 (11)	C26—C25—C24	118.96 (12)
C13—C12—Cl1	117.53 (9)	C26—C25—H25	120.5
C11—C12—Cl1	120.05 (9)	C24—C25—H25	120.5
C12—C13—C14	118.35 (11)	C25—C26—C21	121.99 (12)
C12—C13—H13	120.8	C25—C26—H26	119.0
C14—C13—H13	120.8	C21—C26—H26	119.0
C15—C14—C13	121.43 (11)
C2—O1—C1—C11	179.67 (10)	O2—C2—C21—C26	6.06 (18)
C1—O1—C2—O2	2.90 (17)	O1—C2—C21—C26	−173.90 (10)
C1—O1—C2—C21	−177.14 (10)	O2—C2—C21—C22	−171.70 (12)
O1—C1—C11—C12	167.09 (10)	O1—C2—C21—C22	8.34 (16)
O1—C1—C11—C16	−13.58 (15)	C3—O3—C22—C23	−7.76 (18)
C16—C11—C12—C13	1.25 (18)	C3—O3—C22—C21	171.63 (12)
C1—C11—C12—C13	−179.38 (11)	C26—C21—C22—O3	−177.87 (11)
C16—C11—C12—Cl1	−178.92 (9)	C2—C21—C22—O3	−0.17 (18)
C1—C11—C12—Cl1	0.44 (16)	C26—C21—C22—C23	1.53 (17)
C11—C12—C13—C14	−0.22 (18)	C2—C21—C22—C23	179.23 (11)
Cl1—C12—C13—C14	179.96 (9)	O3—C22—C23—C24	178.65 (12)
C12—C13—C14—C15	−1.10 (19)	C21—C22—C23—C24	−0.73 (18)
C12—C13—C14—Cl2	178.88 (9)	C22—C23—C24—C25	−0.9 (2)
C13—C14—C15—C16	1.3 (2)	C23—C24—C25—C26	1.7 (2)
Cl2—C14—C15—C16	−178.68 (10)	C24—C25—C26—C21	−0.90 (19)
C14—C15—C16—C11	−0.19 (19)	C22—C21—C26—C25	−0.73 (18)
C12—C11—C16—C15	−1.04 (18)	C2—C21—C26—C25	−178.67 (11)
C1—C11—C16—C15	179.60 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2i	0.98	2.59	3.5433 (18)	165
C15—H15···O2i	0.95	2.51	3.3945 (15)	154
C16—H16···O3	0.95	2.48	3.3989 (15)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2i	0.98	2.59	3.5433 (18)	165
C15—H15⋯O2i	0.95	2.51	3.3945 (15)	154
C16—H16⋯O3	0.95	2.48	3.3989 (15)	163

Symmetry code: (i) .