2,4-Dichloro-phenyl benzoate.

The crystal structure of the title compound, C(13)H(8)Cl(2)O(2), resembles those of 2,3-dichloro-phenyl benzoate, 2,4-dimethyl-phenyl benzoate and other aryl benzoates, with similar bond parameters. The plane of central -C(=O)-O- group is inclined at the angle of 9.1 (2)° with respect to the benzoate ring. The two aromatic rings make a dihedral angle of 47.8 (1)°. In the crystal structure there are no classical hydrogen bonds. The mol-ecules in the structure are packed into chains diagonally in the bc plane.

Related literature

For the preparation of the compound, see: Nayak & Gowda (2009 ▶); For related structures, see: Gowda et al. (2007 ▶, 2008 ▶, 2009 ▶).

Experimental

Crystal data

C13H8Cl2O2

M = 267.09

Orthorhombic,

a = 3.9722 (1) Å

b = 11.9458 (3) Å

c = 24.9407 (5) Å

V = 1183.46 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 295 K

0.47 × 0.11 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractomenter with a Ruby (Gemini Mo) detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.751, T max = 0.943

20045 measured reflections

2202 independent reflections

1961 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.059

S = 1.03

2202 reflections

160 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 861 Friedel pairs

Flack parameter: 0.02 (5)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011763/bt2919sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011763/bt2919Isup2.hkl

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

C13H8Cl2O2	F(000) = 544
Mr = 267.09	Dx = 1.499 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10923 reflections
a = 3.9722 (1) Å	θ = 3.3–29.5°
b = 11.9458 (3) Å	µ = 0.53 mm−1
c = 24.9407 (5) Å	T = 295 K
V = 1183.46 (5) Å3	Needle, colourless
Z = 4	0.47 × 0.11 × 0.10 mm

Oxford Diffraction Xcalibur diffractomenter with a Ruby (Gemini Mo) detector	2202 independent reflections
graphite	1961 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.027
ω scans	θmax = 25.5°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −4→4
Tmin = 0.751, Tmax = 0.943	k = −14→14
20045 measured reflections	l = −30→30

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)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.0343P)2 + 0.0694P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2202 reflections	Δρmax = 0.13 e Å−3
160 parameters	Δρmin = −0.15 e Å−3
2 restraints	Absolute structure: Flack (1983), 861 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (5)

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	0.4499 (4)	0.34482 (14)	0.11405 (6)	0.0475 (4)
C2	0.5855 (4)	0.32994 (13)	0.16904 (6)	0.0454 (4)
C3	0.7373 (5)	0.41579 (15)	0.19708 (7)	0.0532 (4)
H3	0.7648	0.4856	0.1811	0.064*
C4	0.8484 (6)	0.39790 (19)	0.24887 (7)	0.0649 (5)
H4	0.947 (5)	0.4659 (16)	0.2689 (8)	0.078*
C5	0.8127 (6)	0.29517 (19)	0.27219 (8)	0.0671 (5)
H5	0.884 (6)	0.2847 (17)	0.3063 (8)	0.081*
C6	0.6657 (6)	0.20918 (18)	0.24438 (8)	0.0709 (6)
H6	0.6437	0.1393	0.2604	0.085*
C7	0.5496 (5)	0.22556 (15)	0.19272 (7)	0.0603 (5)
H7	0.4485	0.1672	0.174	0.072*
C8	0.4313 (4)	0.47198 (13)	0.04142 (6)	0.0439 (4)
C9	0.2560 (4)	0.56988 (13)	0.03415 (6)	0.0436 (4)
C10	0.1619 (4)	0.60433 (13)	−0.01650 (6)	0.0466 (4)
H10	0.0463	0.6712	−0.0215	0.056*
C11	0.2437 (4)	0.53692 (13)	−0.05937 (6)	0.0457 (4)
C12	0.4179 (4)	0.43887 (13)	−0.05300 (6)	0.0489 (4)
H12	0.4704	0.3947	−0.0825	0.059*
C13	0.5148 (4)	0.40651 (14)	−0.00208 (7)	0.0489 (4)
H13	0.636	0.3407	0.0028	0.059*
O1	0.5392 (3)	0.44515 (9)	0.09308 (4)	0.0522 (3)
O2	0.2813 (4)	0.27886 (11)	0.09054 (5)	0.0749 (4)
Cl1	0.14820 (14)	0.65271 (4)	0.088572 (17)	0.06409 (15)
Cl2	0.11922 (13)	0.57737 (4)	−0.123305 (17)	0.06442 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0547 (10)	0.0419 (8)	0.0460 (8)	−0.0075 (9)	0.0057 (8)	−0.0025 (7)
C2	0.0474 (9)	0.0440 (9)	0.0450 (8)	−0.0005 (8)	0.0081 (7)	−0.0007 (7)
C3	0.0588 (10)	0.0515 (10)	0.0493 (9)	−0.0038 (9)	0.0020 (8)	0.0003 (8)
C4	0.0657 (12)	0.0814 (14)	0.0477 (10)	−0.0034 (12)	−0.0026 (9)	−0.0054 (9)
C5	0.0699 (13)	0.0840 (14)	0.0474 (10)	0.0095 (12)	0.0021 (10)	0.0095 (11)
C6	0.0816 (14)	0.0657 (12)	0.0654 (12)	0.0070 (13)	0.0145 (11)	0.0207 (10)
C7	0.0742 (13)	0.0497 (10)	0.0571 (11)	−0.0025 (10)	0.0093 (10)	0.0030 (8)
C8	0.0467 (9)	0.0394 (8)	0.0455 (8)	−0.0080 (8)	−0.0019 (7)	0.0002 (6)
C9	0.0466 (9)	0.0371 (8)	0.0470 (9)	−0.0076 (7)	0.0047 (7)	−0.0072 (7)
C10	0.0479 (9)	0.0401 (8)	0.0517 (9)	0.0020 (8)	0.0019 (8)	−0.0005 (7)
C11	0.0460 (9)	0.0485 (9)	0.0425 (8)	−0.0045 (8)	0.0005 (7)	0.0036 (7)
C12	0.0518 (10)	0.0482 (9)	0.0468 (9)	0.0031 (9)	0.0063 (8)	−0.0060 (7)
C13	0.0516 (9)	0.0411 (9)	0.0541 (9)	0.0043 (8)	0.0012 (8)	0.0009 (7)
O1	0.0667 (8)	0.0424 (6)	0.0475 (6)	−0.0113 (6)	−0.0117 (6)	0.0031 (5)
O2	0.1069 (11)	0.0634 (8)	0.0546 (7)	−0.0411 (8)	−0.0074 (8)	−0.0019 (6)
Cl1	0.0868 (3)	0.0509 (2)	0.0545 (2)	−0.0017 (2)	0.0102 (2)	−0.0149 (2)
Cl2	0.0754 (3)	0.0715 (3)	0.0464 (2)	0.0074 (3)	−0.0040 (2)	0.0055 (2)

C1—O2	1.189 (2)	C7—H7	0.93
C1—O1	1.355 (2)	C8—C9	1.373 (2)
C1—C2	1.484 (2)	C8—C13	1.378 (2)
C2—C3	1.380 (2)	C8—O1	1.3951 (19)
C2—C7	1.387 (2)	C9—C10	1.380 (2)
C3—C4	1.382 (3)	C9—Cl1	1.7334 (15)
C3—H3	0.93	C10—C11	1.378 (2)
C4—C5	1.365 (3)	C10—H10	0.93
C4—H4	1.031 (19)	C11—C12	1.370 (2)
C5—C6	1.370 (3)	C11—Cl2	1.7380 (16)
C5—H5	0.905 (19)	C12—C13	1.382 (2)
C6—C7	1.382 (3)	C12—H12	0.93
C6—H6	0.93	C13—H13	0.93
O2—C1—O1	122.91 (15)	C2—C7—H7	120.3
O2—C1—C2	125.52 (15)	C9—C8—C13	120.10 (14)
O1—C1—C2	111.57 (13)	C9—C8—O1	118.25 (13)
C3—C2—C7	119.82 (16)	C13—C8—O1	121.53 (14)
C3—C2—C1	122.54 (14)	C8—C9—C10	120.81 (14)
C7—C2—C1	117.63 (15)	C8—C9—Cl1	120.54 (12)
C2—C3—C4	119.89 (17)	C10—C9—Cl1	118.65 (13)
C2—C3—H3	120.1	C11—C10—C9	118.18 (15)
C4—C3—H3	120.1	C11—C10—H10	120.9
C5—C4—C3	120.3 (2)	C9—C10—H10	120.9
C5—C4—H4	122.8 (11)	C12—C11—C10	121.94 (15)
C3—C4—H4	116.8 (11)	C12—C11—Cl2	119.22 (13)
C4—C5—C6	120.16 (19)	C10—C11—Cl2	118.85 (12)
C4—C5—H5	119.4 (14)	C11—C12—C13	119.11 (15)
C6—C5—H5	120.4 (14)	C11—C12—H12	120.4
C5—C6—C7	120.52 (18)	C13—C12—H12	120.4
C5—C6—H6	119.7	C8—C13—C12	119.85 (16)
C7—C6—H6	119.7	C8—C13—H13	120.1
C6—C7—C2	119.33 (19)	C12—C13—H13	120.1
C6—C7—H7	120.3	C1—O1—C8	118.64 (12)
O2—C1—C2—C3	−170.23 (18)	O1—C8—C9—Cl1	−4.3 (2)
O1—C1—C2—C3	9.2 (2)	C8—C9—C10—C11	1.0 (2)
O2—C1—C2—C7	8.5 (3)	Cl1—C9—C10—C11	−178.90 (13)
O1—C1—C2—C7	−172.04 (15)	C9—C10—C11—C12	−0.9 (2)
C7—C2—C3—C4	−1.0 (3)	C9—C10—C11—Cl2	178.61 (13)
C1—C2—C3—C4	177.77 (17)	C10—C11—C12—C13	0.0 (2)
C2—C3—C4—C5	0.9 (3)	Cl2—C11—C12—C13	−179.58 (13)
C3—C4—C5—C6	−0.2 (3)	C9—C8—C13—C12	−0.8 (3)
C4—C5—C6—C7	−0.5 (3)	O1—C8—C13—C12	−176.67 (15)
C5—C6—C7—C2	0.4 (3)	C11—C12—C13—C8	0.9 (3)
C3—C2—C7—C6	0.3 (3)	O2—C1—O1—C8	−0.6 (3)
C1—C2—C7—C6	−178.49 (18)	C2—C1—O1—C8	179.94 (14)
C13—C8—C9—C10	−0.2 (2)	C9—C8—O1—C1	125.12 (16)
O1—C8—C9—C10	175.80 (14)	C13—C8—O1—C1	−59.0 (2)
C13—C8—C9—Cl1	179.76 (13)