3-Chloro­phenyl benzoate

The C=O group in the title compound, C₁₃H₉ClO₂, is syn to the chloro group. The two aromatic rings are twisted by 56.88 (6)°. Adjacent mol­ecules are linked via weak C—H...O hydrogen bonding into a linear chain.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.135
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       1000 Deg.
PLAT180_ALERT_4_C Check Cell Rounding: # of Values Ending with 0 =          4

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   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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S1. Comment

As part of a study of the substituent effects on the structures of aryl benzoates (Gowda et al., 2007a, b, c), in the present work, the structure of 3-chlorophenyl benzoate (3CPBA) has been determined. The conformation of the C=O bond in 3CPBA is syn to the meta-chloro group in the phenolic benzene ring (Fig. 1), in contrast to the anti conformations of the C=O bond and the meta-methyl group in 3-methylphenyl benzoate (3MePBA) (Gowda et al., 2007a). The bond parameters in 3CPBA are similar to those of 3MePBA (Gowda et al., 2007a), 2,3-dichlorophenyl benzoate (23DCPBA)(Gowda et al., 2007c), 3,4-dichlorophenyl benzoate(34DCPBA) (Gowda et al., 2007b) and other aryl benzoates (Gowda et al., 2007a, b, c). The dihedral angle between the benzene and benzoyl rings in 3CPBA is 56.88 (6)°, compared to the values of 79.61 (6)° in 3MePBA, 50.16 (7)° in 23DCPBA and 53.77 (5)° in 34DCPBA. The packing diagram of the crystal structure in which the molecules are connected via intermolecular C—H—O hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature

For previous studies, see: Gowda et al. (2007a,b,c); Nayak & Gowda (2008).

S2. Experimental

The title compound was prepared according to the method of Nayak & Gowda (2008). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Nayak & Gowda, 2008). The single crystals used in X-ray diffraction studies were obtained by the slow evaporation of an ethanolic solution of the title compound at room temperature.

S3. Refinement

All H atoms were included in the riding-model approximation with C—H = 0.93 Å, and with U_iso(H) = 1.2xU_eq(C).

Computing details

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); 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 (Sheldrick, 2008).

Figures

	Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound.

3-Chlorophenyl benzoate

Crystal data

C13H9ClO2	Z = 2
Mr = 232.65	F(000) = 240
Triclinic, P1	Dx = 1.405 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 6.0734 (6) Å	Cell parameters from 25 reflections
b = 8.389 (1) Å	θ = 5.6–31.7°
c = 11.747 (2) Å	µ = 2.92 mm^−1
α = 107.89 (1)°	T = 299 K
β = 102.98 (1)°	Prism, colourless
γ = 93.25 (1)°	0.60 × 0.55 × 0.50 mm
V = 549.89 (13) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	1872 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.086
Graphite monochromator	θmax = 66.9°, θmin = 4.1°
ω/2θ scans	h = −7→1
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.197, Tmax = 0.233	l = −13→14
2143 measured reflections	3 standard reflections every 120 min
1947 independent reflections	intensity decay: 1.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0771P)^2 + 0.1623P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.002
1947 reflections	Δρmax = 0.30 e Å^−3
146 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.149 (8)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.29134 (10)	0.17688 (7)	−0.06457 (6)	0.0678 (3)
O1	0.2384 (2)	0.74790 (18)	0.23750 (15)	0.0565 (4)
O2	0.5777 (2)	0.70473 (19)	0.33852 (15)	0.0587 (4)
C1	0.1614 (3)	0.5746 (2)	0.18489 (18)	0.0474 (5)
C2	0.2647 (3)	0.4730 (2)	0.10218 (19)	0.0477 (5)
H2	0.3962	0.5149	0.0869	0.057*
C3	0.1670 (3)	0.3070 (3)	0.04263 (19)	0.0482 (5)
C4	−0.0281 (3)	0.2436 (3)	0.0636 (2)	0.0546 (5)
H4	−0.0937	0.1321	0.0212	0.065*
C5	−0.1247 (4)	0.3482 (3)	0.1485 (2)	0.0593 (6)
H5	−0.2549	0.3060	0.1647	0.071*
C6	−0.0314 (3)	0.5149 (3)	0.2099 (2)	0.0555 (5)
H6	−0.0977	0.5853	0.2669	0.067*
C7	0.4554 (3)	0.7994 (3)	0.30835 (17)	0.0458 (5)
C8	0.5176 (3)	0.9840 (3)	0.34208 (17)	0.0457 (5)
C9	0.3622 (4)	1.0902 (3)	0.3149 (2)	0.0568 (5)
H9	0.2109	1.0464	0.2740	0.068*
C10	0.4331 (5)	1.2610 (3)	0.3487 (2)	0.0680 (7)
H10	0.3287	1.3323	0.3307	0.082*
C11	0.6556 (5)	1.3268 (3)	0.4086 (2)	0.0692 (7)
H11	0.7018	1.4423	0.4315	0.083*
C12	0.8107 (5)	1.2214 (3)	0.4347 (2)	0.0717 (7)
H12	0.9619	1.2658	0.4752	0.086*
C13	0.7428 (4)	1.0512 (3)	0.4013 (2)	0.0602 (6)
H13	0.8486	0.9804	0.4184	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0704 (4)	0.0528 (4)	0.0800 (5)	0.0084 (3)	0.0358 (3)	0.0095 (3)
O1	0.0472 (8)	0.0453 (8)	0.0692 (9)	0.0134 (6)	0.0057 (6)	0.0131 (7)
O2	0.0543 (8)	0.0553 (9)	0.0681 (10)	0.0198 (7)	0.0096 (7)	0.0247 (7)
C1	0.0436 (9)	0.0457 (11)	0.0534 (11)	0.0114 (8)	0.0092 (8)	0.0183 (9)
C2	0.0429 (10)	0.0475 (11)	0.0581 (11)	0.0066 (8)	0.0177 (8)	0.0215 (9)
C3	0.0471 (10)	0.0478 (11)	0.0560 (11)	0.0098 (8)	0.0179 (8)	0.0218 (9)
C4	0.0502 (11)	0.0492 (11)	0.0667 (13)	0.0021 (8)	0.0140 (9)	0.0241 (10)
C5	0.0447 (11)	0.0721 (15)	0.0711 (14)	0.0048 (9)	0.0210 (9)	0.0335 (12)
C6	0.0464 (10)	0.0671 (14)	0.0574 (12)	0.0162 (9)	0.0192 (9)	0.0211 (10)
C7	0.0452 (10)	0.0506 (11)	0.0456 (10)	0.0152 (8)	0.0148 (8)	0.0176 (8)
C8	0.0498 (10)	0.0493 (11)	0.0412 (9)	0.0133 (8)	0.0146 (8)	0.0161 (8)
C9	0.0574 (12)	0.0549 (13)	0.0593 (12)	0.0174 (9)	0.0124 (9)	0.0202 (10)
C10	0.0885 (17)	0.0525 (13)	0.0701 (15)	0.0255 (12)	0.0225 (12)	0.0254 (11)
C11	0.0935 (18)	0.0520 (13)	0.0634 (14)	0.0038 (12)	0.0272 (12)	0.0169 (11)
C12	0.0675 (15)	0.0653 (15)	0.0712 (15)	−0.0050 (11)	0.0129 (11)	0.0128 (12)
C13	0.0534 (12)	0.0594 (13)	0.0630 (13)	0.0109 (10)	0.0076 (9)	0.0177 (11)

Geometric parameters (Å, º)

Cl1—C3	1.739 (2)	C6—H6	0.9300
O1—C7	1.356 (2)	C7—C8	1.479 (3)
O1—C1	1.399 (2)	C8—C13	1.384 (3)
O2—C7	1.195 (2)	C8—C9	1.387 (3)
C1—C2	1.374 (3)	C9—C10	1.378 (3)
C1—C6	1.374 (3)	C9—H9	0.9300
C2—C3	1.380 (3)	C10—C11	1.370 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.374 (3)	C11—C12	1.376 (4)
C4—C5	1.376 (3)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.371 (4)
C5—C6	1.379 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C7—O1—C1	118.81 (14)	O2—C7—C8	125.42 (19)
C2—C1—C6	122.04 (19)	O1—C7—C8	111.50 (15)
C2—C1—O1	120.12 (18)	C13—C8—C9	119.3 (2)
C6—C1—O1	117.55 (18)	C13—C8—C7	117.74 (18)
C1—C2—C3	117.83 (17)	C9—C8—C7	122.95 (18)
C1—C2—H2	121.1	C10—C9—C8	119.6 (2)
C3—C2—H2	121.1	C10—C9—H9	120.2
C4—C3—C2	121.76 (19)	C8—C9—H9	120.2
C4—C3—Cl1	119.48 (17)	C11—C10—C9	120.7 (2)
C2—C3—Cl1	118.73 (14)	C11—C10—H10	119.7
C3—C4—C5	118.8 (2)	C9—C10—H10	119.7
C3—C4—H4	120.6	C10—C11—C12	119.8 (2)
C5—C4—H4	120.6	C10—C11—H11	120.1
C4—C5—C6	120.99 (19)	C12—C11—H11	120.1
C4—C5—H5	119.5	C13—C12—C11	120.2 (2)
C6—C5—H5	119.5	C13—C12—H12	119.9
C1—C6—C5	118.6 (2)	C11—C12—H12	119.9
C1—C6—H6	120.7	C12—C13—C8	120.4 (2)
C5—C6—H6	120.7	C12—C13—H13	119.8
O2—C7—O1	123.08 (19)	C8—C13—H13	119.8
C7—O1—C1—C2	−61.9 (2)	C1—O1—C7—C8	172.24 (16)
C7—O1—C1—C6	124.2 (2)	O2—C7—C8—C13	7.9 (3)
C6—C1—C2—C3	0.7 (3)	O1—C7—C8—C13	−172.14 (18)
O1—C1—C2—C3	−172.97 (16)	O2—C7—C8—C9	−173.4 (2)
C1—C2—C3—C4	0.5 (3)	O1—C7—C8—C9	6.6 (3)
C1—C2—C3—Cl1	178.84 (14)	C13—C8—C9—C10	−1.0 (3)
C2—C3—C4—C5	−1.5 (3)	C7—C8—C9—C10	−179.7 (2)
Cl1—C3—C4—C5	−179.86 (16)	C8—C9—C10—C11	0.2 (4)
C3—C4—C5—C6	1.4 (3)	C9—C10—C11—C12	0.4 (4)
C2—C1—C6—C5	−0.8 (3)	C10—C11—C12—C13	−0.2 (4)
O1—C1—C6—C5	173.01 (18)	C11—C12—C13—C8	−0.6 (4)
C4—C5—C6—C1	−0.3 (3)	C9—C8—C13—C12	1.2 (3)
C1—O1—C7—O2	−7.8 (3)	C7—C8—C13—C12	180.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2^i	0.93	2.46	3.319 (3)	154

Symmetry code: (i) x−1, y, z.