4-Chloro-phenyl 4-chloro-benzoate.

The structure of the title compound (4CP4CBA), C(13)H(8)Cl(2)O(2), resembles those of 4-methyl-phenyl 4-chloro-benzoate (4MP4CBA), 4-chloro-phenyl 4-methyl-benzoate (4CP4MBA) and 4-methyl-phenyl 4-methyl-benzoate (4MP4MBA), with similar bond parameters. The dihedral angle between the two benzene rings in 4CP4CBA is 47.98 (7)°, compared with 51.86 (4)° in 4MP4CBA, 63.89 (8)° in 4CP4MBA and 63.57 (5)° in 4MP4MBA. In the crystal structure, mol-ecules are linked into helical chains running along the b axis by C-H-O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C13H8Cl2O2

M = 267.09

Monoclinic,

a = 15.370 (2) Å

b = 3.9528 (4) Å

c = 19.465 (2) Å

β = 91.804 (9)°

V = 1182.0 (2) Å3

Z = 4

Cu Kα radiation

μ = 4.83 mm−1

T = 299 (2) K

0.45 × 0.23 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.194, T max = 0.420

4211 measured reflections

2109 independent reflections

1724 reflections with I > 2σ(I)

R int = 0.080

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.139

S = 1.05

2109 reflections

178 parameters

Only H-atom coordinates refined

Δρmax = 0.39 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536808022800/ci2640sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022800/ci2640Isup2.hkl

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

C13H8Cl2O2	F000 = 544
Mr = 267.09	Dx = 1.501 Mg m−3
Monoclinic, P21/n	Cu Kα radiation λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 15.370 (2) Å	θ = 11.5–24.3º
b = 3.9528 (4) Å	µ = 4.83 mm−1
c = 19.465 (2) Å	T = 299 (2) K
β = 91.804 (9)º	Rod, colourless
V = 1182.0 (2) Å3	0.45 × 0.23 × 0.18 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.080
Radiation source: fine-focus sealed tube	θmax = 67.0º
Monochromator: graphite	θmin = 3.6º
T = 299(2) K	h = −18→18
ω/2θ scans	k = −4→0
Absorption correction: ψ scan(North et al., 1968)	l = −23→23
Tmin = 0.194, Tmax = 0.420	3 standard reflections
4211 measured reflections	every 120 min
2109 independent reflections	intensity decay: 1.0%
1724 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Only H-atom coordinates refined
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0736P)2 + 0.2805P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.021
2109 reflections	Δρmax = 0.39 e Å−3
178 parameters	Δρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.49228 (5)	0.7640 (2)	0.08027 (4)	0.0690 (3)
Cl2	0.72347 (5)	−0.0839 (2)	0.67678 (3)	0.0704 (3)
O1	0.59363 (10)	0.3353 (5)	0.36024 (9)	0.0529 (5)
O2	0.72448 (12)	0.5904 (7)	0.36130 (10)	0.0737 (7)
C1	0.57335 (13)	0.4453 (6)	0.29332 (12)	0.0444 (5)
C2	0.49523 (15)	0.6088 (7)	0.28247 (14)	0.0518 (6)
H2	0.4603 (19)	0.657 (8)	0.3193 (16)	0.062*
C3	0.46945 (15)	0.7062 (7)	0.21667 (15)	0.0546 (6)
H3	0.4132 (19)	0.820 (9)	0.2133 (15)	0.066*
C4	0.52292 (14)	0.6377 (6)	0.16294 (13)	0.0469 (5)
C5	0.60108 (15)	0.4709 (7)	0.17399 (13)	0.0492 (6)
H5	0.6337 (18)	0.438 (8)	0.1358 (16)	0.059*
C6	0.62658 (14)	0.3724 (7)	0.23892 (13)	0.0488 (6)
H6	0.6762 (19)	0.246 (8)	0.2482 (15)	0.059*
C7	0.67225 (14)	0.4158 (7)	0.38938 (12)	0.0482 (6)
C8	0.68345 (13)	0.2812 (6)	0.45961 (12)	0.0452 (5)
C9	0.61746 (15)	0.1152 (8)	0.49299 (14)	0.0530 (6)
H9	0.5619 (19)	0.089 (8)	0.4691 (16)	0.064*
C10	0.62957 (16)	0.0048 (8)	0.55961 (13)	0.0538 (6)
H10	0.584 (2)	−0.108 (8)	0.5807 (16)	0.065*
C11	0.70901 (15)	0.0570 (7)	0.59276 (13)	0.0494 (6)
C12	0.77573 (16)	0.2151 (8)	0.56050 (15)	0.0579 (7)
H12	0.826 (2)	0.225 (9)	0.5856 (17)	0.069*
C13	0.76306 (14)	0.3276 (8)	0.49402 (14)	0.0534 (6)
H13	0.8067 (19)	0.428 (9)	0.4718 (16)	0.064*

	U11	U22	U33	U12	U13	U23
Cl1	0.0694 (4)	0.0793 (5)	0.0574 (4)	0.0037 (3)	−0.0138 (3)	0.0097 (4)
Cl2	0.0777 (5)	0.0819 (6)	0.0507 (4)	0.0114 (4)	−0.0142 (3)	0.0012 (3)
O1	0.0419 (8)	0.0685 (12)	0.0480 (9)	−0.0142 (8)	−0.0015 (6)	0.0071 (9)
O2	0.0623 (11)	0.0998 (18)	0.0589 (11)	−0.0387 (11)	0.0032 (9)	0.0064 (11)
C1	0.0394 (10)	0.0469 (13)	0.0469 (12)	−0.0087 (9)	0.0002 (9)	−0.0007 (11)
C2	0.0404 (11)	0.0604 (16)	0.0553 (14)	−0.0009 (10)	0.0094 (10)	−0.0063 (12)
C3	0.0395 (11)	0.0581 (15)	0.0659 (16)	0.0061 (11)	−0.0023 (10)	−0.0024 (13)
C4	0.0447 (11)	0.0462 (13)	0.0492 (12)	−0.0044 (10)	−0.0046 (9)	0.0006 (11)
C5	0.0451 (11)	0.0537 (14)	0.0491 (13)	0.0034 (10)	0.0054 (10)	−0.0044 (12)
C6	0.0393 (11)	0.0553 (14)	0.0518 (13)	0.0056 (10)	0.0007 (9)	−0.0009 (12)
C7	0.0378 (10)	0.0605 (15)	0.0463 (12)	−0.0070 (10)	0.0038 (9)	−0.0042 (11)
C8	0.0367 (10)	0.0513 (13)	0.0477 (13)	−0.0032 (9)	0.0027 (9)	−0.0065 (11)
C9	0.0368 (10)	0.0715 (17)	0.0504 (13)	−0.0101 (11)	−0.0043 (9)	0.0033 (12)
C10	0.0428 (11)	0.0678 (16)	0.0507 (13)	−0.0070 (12)	0.0003 (10)	0.0049 (13)
C11	0.0514 (12)	0.0502 (14)	0.0460 (12)	0.0065 (10)	−0.0064 (10)	−0.0059 (11)
C12	0.0413 (11)	0.0657 (17)	0.0659 (16)	0.0002 (11)	−0.0123 (11)	−0.0106 (14)
C13	0.0356 (10)	0.0625 (16)	0.0622 (15)	−0.0079 (11)	0.0026 (10)	−0.0057 (13)

Cl1—C4	1.736 (3)	C5—H5	0.92 (3)
Cl2—C11	1.735 (3)	C6—H6	0.93 (3)
O1—C7	1.356 (3)	C7—C8	1.472 (3)
O1—C1	1.399 (3)	C8—C9	1.387 (3)
O2—C7	1.203 (3)	C8—C13	1.389 (3)
C1—C2	1.374 (3)	C9—C10	1.375 (4)
C1—C6	1.389 (3)	C9—H9	0.96 (3)
C2—C3	1.383 (4)	C10—C11	1.379 (3)
C2—H2	0.93 (3)	C10—H10	0.93 (3)
C3—C4	1.377 (4)	C11—C12	1.370 (4)
C3—H3	0.97 (3)	C12—C13	1.376 (4)
C4—C5	1.381 (3)	C12—H12	0.90 (3)
C5—C6	1.368 (4)	C13—H13	0.90 (3)
C7—O1—C1	119.07 (17)	O2—C7—C8	124.7 (2)
C2—C1—C6	120.9 (2)	O1—C7—C8	112.34 (19)
C2—C1—O1	117.2 (2)	C9—C8—C13	118.9 (2)
C6—C1—O1	121.7 (2)	C9—C8—C7	122.7 (2)
C1—C2—C3	119.8 (2)	C13—C8—C7	118.4 (2)
C1—C2—H2	120.1 (19)	C10—C9—C8	120.8 (2)
C3—C2—H2	120.1 (19)	C10—C9—H9	120.8 (18)
C4—C3—C2	119.2 (2)	C8—C9—H9	118.3 (18)
C4—C3—H3	126.1 (17)	C11—C10—C9	119.0 (2)
C2—C3—H3	114.7 (17)	C11—C10—H10	122 (2)
C3—C4—C5	120.8 (2)	C9—C10—H10	119 (2)
C3—C4—Cl1	119.77 (19)	C12—C11—C10	121.2 (2)
C5—C4—Cl1	119.41 (19)	C12—C11—Cl2	120.19 (19)
C6—C5—C4	120.1 (2)	C10—C11—Cl2	118.6 (2)
C6—C5—H5	124.0 (19)	C11—C12—C13	119.5 (2)
C4—C5—H5	115.8 (19)	C11—C12—H12	114 (2)
C5—C6—C1	119.1 (2)	C13—C12—H12	126 (2)
C5—C6—H6	123.0 (18)	C12—C13—C8	120.5 (2)
C1—C6—H6	117.8 (18)	C12—C13—H13	121 (2)
O2—C7—O1	122.9 (2)	C8—C13—H13	119 (2)
C7—O1—C1—C2	−129.5 (3)	O2—C7—C8—C9	172.1 (3)
C7—O1—C1—C6	55.0 (3)	O1—C7—C8—C9	−4.8 (4)
C6—C1—C2—C3	−0.8 (4)	O2—C7—C8—C13	−6.9 (4)
O1—C1—C2—C3	−176.3 (2)	O1—C7—C8—C13	176.2 (2)
C1—C2—C3—C4	−0.1 (4)	C13—C8—C9—C10	1.5 (4)
C2—C3—C4—C5	0.7 (4)	C7—C8—C9—C10	−177.5 (3)
C2—C3—C4—Cl1	−179.0 (2)	C8—C9—C10—C11	−0.9 (4)
C3—C4—C5—C6	−0.3 (4)	C9—C10—C11—C12	−0.2 (4)
Cl1—C4—C5—C6	179.4 (2)	C9—C10—C11—Cl2	−179.9 (2)
C4—C5—C6—C1	−0.6 (4)	C10—C11—C12—C13	0.7 (4)
C2—C1—C6—C5	1.1 (4)	Cl2—C11—C12—C13	−179.5 (2)
O1—C1—C6—C5	176.5 (2)	C11—C12—C13—C8	−0.1 (4)
C1—O1—C7—O2	3.2 (4)	C9—C8—C13—C12	−1.0 (4)
C1—O1—C7—C8	−179.9 (2)	C7—C8—C13—C12	178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.92 (3)	2.58 (3)	3.168 (3)	123 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.92 (3)	2.58 (3)	3.168 (3)	123 (2)

Symmetry code: (i) .