3,5-Dichloro-phenyl 4-methyl-benzoate.

The structure of the title compound, C(14)H(10)Cl(2)O(2), resembles those of 3-chloro-phenyl 4-methyl-benzoate, 2,6-dichloro-phenyl 4-methyl-benzoate and 2,4-dichloro-phenyl 4-methyl-benzoate, with similar bond parameters. The dihedral angle between the benzene and benzoyl rings is 48.81 (6)°.

Related literature

For related literature, see: Gowda et al. (2007 ▶, 2008a ▶,b ▶); Nayak & Gowda (2008 ▶).

Experimental

Crystal data

C14H10Cl2O2

M = 281.12

Monoclinic,

a = 3.9273 (6) Å

b = 28.412 (4) Å

c = 11.705 (1) Å

β = 94.06 (1)°

V = 1302.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 299 (2) K

0.48 × 0.40 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.800, T max = 0.962

7613 measured reflections

2621 independent reflections

1755 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.139

S = 1.11

2621 reflections

184 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022277/bx2159sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022277/bx2159Isup2.hkl

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

C14H10Cl2O2	F000 = 576
Mr = 281.12	Dx = 1.433 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3406 reflections
a = 3.9273 (6) Å	θ = 2.3–27.9º
b = 28.412 (4) Å	µ = 0.49 mm−1
c = 11.705 (1) Å	T = 299 (2) K
β = 94.06 (1)º	Plate, colourless
V = 1302.8 (3) Å3	0.48 × 0.40 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2621 independent reflections
Radiation source: fine-focus sealed tube	1755 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 299(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 2.3º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −4→4
Tmin = 0.800, Tmax = 0.962	k = −35→34
7613 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0783P)2] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
2621 reflections	Δρmax = 0.32 e Å−3
184 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. CrysAlis RED, Oxford Diffraction Ltd., 2007 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.4042 (6)	0.15541 (8)	−0.1194 (2)	0.0418 (6)
C2	0.2829 (6)	0.13459 (9)	−0.0235 (2)	0.0444 (6)
H2	0.200 (6)	0.1519 (9)	0.035 (2)	0.053*
C3	0.2772 (6)	0.08640 (9)	−0.01881 (19)	0.0419 (6)
C4	0.3809 (6)	0.05839 (9)	−0.1061 (2)	0.0442 (6)
H4	0.373 (5)	0.0228 (10)	−0.0960 (19)	0.053*
C5	0.4990 (6)	0.08058 (9)	−0.20047 (19)	0.0413 (6)
C6	0.5140 (6)	0.12902 (9)	−0.2088 (2)	0.0432 (6)
H6	0.583 (6)	0.1444 (9)	−0.270 (2)	0.052*
C7	0.5453 (6)	0.23217 (9)	−0.0486 (2)	0.0450 (6)
C8	0.4837 (6)	0.28221 (8)	−0.0721 (2)	0.0405 (6)
C9	0.3278 (7)	0.29931 (10)	−0.1734 (2)	0.0492 (7)
H9	0.260 (7)	0.2789 (10)	−0.231 (2)	0.059*
C10	0.2734 (7)	0.34658 (10)	−0.1884 (2)	0.0506 (7)
H10	0.164 (6)	0.3558 (9)	−0.263 (2)	0.061*
C11	0.3722 (6)	0.37871 (9)	−0.1031 (2)	0.0437 (6)
C12	0.5333 (7)	0.36165 (10)	−0.0028 (2)	0.0477 (7)
H12	0.607 (6)	0.3843 (9)	0.049 (2)	0.057*
C13	0.5880 (7)	0.31429 (9)	0.0140 (2)	0.0464 (7)
H13	0.689 (6)	0.3038 (9)	0.079 (2)	0.056*
C14	0.3049 (8)	0.43029 (10)	−0.1188 (3)	0.0598 (8)
H14A	0.5179	0.4468	−0.1197	0.072*
H14B	0.1808	0.4417	−0.0567	0.072*
H14C	0.1729	0.4354	−0.1899	0.072*
O1	0.3978 (5)	0.20416 (6)	−0.13445 (15)	0.0544 (5)
O2	0.7075 (5)	0.21609 (6)	0.03319 (17)	0.0650 (6)
Cl1	0.13414 (18)	0.05912 (3)	0.10169 (6)	0.0602 (3)
Cl2	0.6296 (2)	0.04648 (2)	−0.31227 (6)	0.0605 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0491 (15)	0.0345 (15)	0.0402 (13)	0.0037 (11)	−0.0078 (11)	−0.0019 (10)
C2	0.0466 (15)	0.0452 (16)	0.0408 (14)	0.0089 (12)	−0.0020 (11)	−0.0037 (11)
C3	0.0391 (13)	0.0472 (16)	0.0389 (13)	0.0018 (11)	0.0000 (10)	0.0042 (11)
C4	0.0464 (15)	0.0382 (15)	0.0473 (15)	0.0007 (11)	−0.0014 (11)	0.0021 (11)
C5	0.0436 (14)	0.0397 (14)	0.0402 (13)	0.0001 (11)	−0.0003 (10)	−0.0035 (11)
C6	0.0460 (14)	0.0445 (16)	0.0384 (13)	−0.0056 (12)	−0.0014 (11)	0.0015 (11)
C7	0.0496 (15)	0.0404 (15)	0.0443 (14)	0.0022 (12)	−0.0024 (12)	−0.0045 (11)
C8	0.0396 (13)	0.0399 (15)	0.0414 (13)	0.0021 (11)	0.0000 (10)	−0.0020 (11)
C9	0.0616 (17)	0.0426 (16)	0.0425 (15)	−0.0007 (13)	−0.0017 (12)	−0.0020 (12)
C10	0.0597 (17)	0.0440 (17)	0.0468 (15)	0.0019 (12)	−0.0043 (13)	0.0081 (12)
C11	0.0448 (14)	0.0384 (15)	0.0493 (15)	0.0026 (11)	0.0122 (11)	0.0029 (11)
C12	0.0562 (16)	0.0397 (16)	0.0470 (15)	−0.0010 (12)	0.0016 (12)	−0.0072 (12)
C13	0.0540 (16)	0.0407 (16)	0.0433 (15)	0.0034 (12)	−0.0059 (12)	−0.0013 (12)
C14	0.0715 (19)	0.0452 (18)	0.0641 (19)	0.0082 (14)	0.0148 (14)	0.0106 (13)
O1	0.0802 (13)	0.0341 (11)	0.0465 (10)	0.0014 (9)	−0.0120 (9)	−0.0001 (8)
O2	0.0828 (14)	0.0442 (11)	0.0635 (12)	0.0109 (10)	−0.0274 (11)	−0.0019 (9)
Cl1	0.0681 (5)	0.0635 (5)	0.0504 (4)	−0.0026 (3)	0.0136 (3)	0.0100 (3)
Cl2	0.0806 (5)	0.0503 (5)	0.0521 (4)	0.0015 (4)	0.0149 (3)	−0.0108 (3)

C1—C6	1.382 (3)	C8—C9	1.383 (4)
C1—C2	1.382 (3)	C8—C13	1.398 (3)
C1—O1	1.396 (3)	C9—C10	1.369 (4)
C2—C3	1.371 (3)	C9—H9	0.91 (3)
C2—H2	0.92 (3)	C10—C11	1.387 (4)
C3—C4	1.379 (3)	C10—H10	0.98 (3)
C3—Cl1	1.737 (2)	C11—C12	1.382 (3)
C4—C5	1.381 (3)	C11—C14	1.498 (3)
C4—H4	1.02 (3)	C12—C13	1.375 (4)
C5—C6	1.382 (3)	C12—H12	0.91 (3)
C5—Cl2	1.735 (2)	C13—H13	0.89 (3)
C6—H6	0.89 (3)	C14—H14A	0.9600
C7—O2	1.202 (3)	C14—H14B	0.9600
C7—O1	1.377 (3)	C14—H14C	0.9600
C7—C8	1.465 (3)
C6—C1—C2	121.8 (2)	C13—C8—C7	117.5 (2)
C6—C1—O1	116.5 (2)	C10—C9—C8	120.7 (2)
C2—C1—O1	121.5 (2)	C10—C9—H9	119.5 (18)
C3—C2—C1	117.9 (2)	C8—C9—H9	119.9 (18)
C3—C2—H2	119.8 (16)	C9—C10—C11	121.3 (3)
C1—C2—H2	122.3 (16)	C9—C10—H10	115.5 (16)
C2—C3—C4	122.7 (2)	C11—C10—H10	123.2 (16)
C2—C3—Cl1	119.06 (19)	C12—C11—C10	117.9 (2)
C4—C3—Cl1	118.25 (19)	C12—C11—C14	120.9 (2)
C3—C4—C5	117.6 (2)	C10—C11—C14	121.2 (2)
C3—C4—H4	118.3 (13)	C13—C12—C11	121.5 (3)
C5—C4—H4	124.1 (13)	C13—C12—H12	123.8 (17)
C4—C5—C6	122.0 (2)	C11—C12—H12	114.7 (17)
C4—C5—Cl2	118.88 (19)	C12—C13—C8	120.0 (2)
C6—C5—Cl2	119.10 (18)	C12—C13—H13	120.5 (17)
C5—C6—C1	118.0 (2)	C8—C13—H13	119.5 (17)
C5—C6—H6	124.0 (17)	C11—C14—H14A	109.5
C1—C6—H6	117.9 (17)	C11—C14—H14B	109.5
O2—C7—O1	122.2 (2)	H14A—C14—H14B	109.5
O2—C7—C8	126.1 (2)	C11—C14—H14C	109.5
O1—C7—C8	111.6 (2)	H14A—C14—H14C	109.5
C9—C8—C13	118.6 (2)	H14B—C14—H14C	109.5
C9—C8—C7	124.0 (2)	C7—O1—C1	118.56 (18)
C6—C1—C2—C3	0.6 (4)	O1—C7—C8—C13	173.3 (2)
O1—C1—C2—C3	175.7 (2)	C13—C8—C9—C10	−0.8 (4)
C1—C2—C3—C4	−1.2 (4)	C7—C8—C9—C10	178.9 (2)
C1—C2—C3—Cl1	178.75 (18)	C8—C9—C10—C11	0.0 (4)
C2—C3—C4—C5	0.9 (4)	C9—C10—C11—C12	1.1 (4)
Cl1—C3—C4—C5	−179.01 (18)	C9—C10—C11—C14	−178.5 (2)
C3—C4—C5—C6	−0.1 (4)	C10—C11—C12—C13	−1.5 (4)
C3—C4—C5—Cl2	−179.67 (18)	C14—C11—C12—C13	178.1 (2)
C4—C5—C6—C1	−0.4 (4)	C11—C12—C13—C8	0.8 (4)
Cl2—C5—C6—C1	179.14 (18)	C9—C8—C13—C12	0.3 (4)
C2—C1—C6—C5	0.2 (4)	C7—C8—C13—C12	−179.3 (2)
O1—C1—C6—C5	−175.2 (2)	O2—C7—O1—C1	7.5 (4)
O2—C7—C8—C9	172.5 (3)	C8—C7—O1—C1	−173.6 (2)
O1—C7—C8—C9	−6.3 (4)	C6—C1—O1—C7	−131.0 (2)
O2—C7—C8—C13	−7.9 (4)	C2—C1—O1—C7	53.6 (3)