3-Chloro­phenyl benzoate

Gowda, B.T.; Foro, S.; Babitha, K.S.; Fuess, H.

doi:10.1107/S1600536808022721

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1587

doi:10.1107/S1600536808022721

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3-Chlorophenyl benzoate

B. Thimme Gowda,^a ^* Sabine Foro,^b K. S. Babitha ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 9 July 2008; accepted 19 July 2008; online 26 July 2008)

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.

Related literature

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

Experimental

Crystal data

C₁₃H₉ClO₂
M_r = 232.65
Triclinic, $[P \overline 1]$
a = 6.0734 (6) Å
b = 8.389 (1) Å
c = 11.747 (2) Å
α = 107.89 (1)°
β = 102.98 (1)°
γ = 93.25 (1)°
V = 549.89 (13) Å³
Z = 2
Cu Kα radiation
μ = 2.92 mm⁻¹
T = 299 (2) K
0.60 × 0.55 × 0.50 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.197, T_max = 0.233
2143 measured reflections
1947 independent reflections
1872 reflections with I > 2σ(I)
R_int = 0.086
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.135
S = 1.10
1947 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.93	2.46	3.319 (3)	154
Symmetry code: (i) x-1, y, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022721/ng2472sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022721/ng2472Isup2.hkl

checkCIF report

Comment top

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 top

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

Experimental top

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.

Computing details top

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 top

	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 top

Crystal data top

C₁₃H₉ClO₂	Z = 2
M_r = 232.65	F(000) = 240
Triclinic, P1	D_x = 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) Å³

Data collection top

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

Refinement top

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0771P)² + 0.1623P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.002
1947 reflections	Δρ_max = 0.30 e Å⁻³
146 parameters	Δρ_min = −0.34 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.149 (8)

Crystal data top

C₁₃H₉ClO₂	γ = 93.25 (1)°
M_r = 232.65	V = 549.89 (13) Å³
Triclinic, P1	Z = 2
a = 6.0734 (6) Å	Cu Kα radiation
b = 8.389 (1) Å	µ = 2.92 mm⁻¹
c = 11.747 (2) Å	T = 299 K
α = 107.89 (1)°	0.60 × 0.55 × 0.50 mm
β = 102.98 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1872 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.086
T_min = 0.197, T_max = 0.233	3 standard reflections every 120 min
2143 measured reflections	intensity decay: 1.0%
1947 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.10	Δρ_max = 0.30 e Å⁻³
1947 reflections	Δρ_min = −0.34 e Å⁻³
146 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.93	2.46	3.319 (3)	154

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₉ClO₂
M_r	232.65
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	6.0734 (6), 8.389 (1), 11.747 (2)
α, β, γ (°)	107.89 (1), 102.98 (1), 93.25 (1)
V (Å³)	549.89 (13)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.92
Crystal size (mm)	0.60 × 0.55 × 0.50

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.197, 0.233
No. of measured, independent and observed [I > 2σ(I)] reflections	2143, 1947, 1872
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.135, 1.10
No. of reflections	1947
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.34

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.93	2.46	3.319 (3)	153.7

Symmetry code: (i) x−1, y, z.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

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