2-(4-Chloro­phen­yl)-2-oxoethyl benzoate

Fun, H.-K.; Shahani, T.; Garudachari, B.; Isloor, A.M.; Satyganarayan, M.N.

doi:10.1107/S160053681102383X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1802

doi:10.1107/S160053681102383X

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2-(4-Chlorophenyl)-2-oxoethyl benzoate

Hoong-Kun Fun,^a ^*‡ Tara Shahani,^a B. Garudachari,^b Arun M. Isloor ^b and M. N. Satyganarayan ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bOrganic Electronics Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^cDepartment of Physics, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 17 June 2011; accepted 17 June 2011; online 25 June 2011)

In the title compound, C₁₅H₁₁ClO₃, the dihedral angle between the aromatic rings is 84.29 (8)°. In the crystal, molecules are linked by weak C—H⋯π interactions.

Related literature

For applications of phenacyl benzoate derivatives, see: Rather & Reid (1919 ); Litera et al. (2006 ); Huang et al. (1996 ); Gandhi et al. (1995 ). For related structures, see: Ogata et al. (1987 ); Wan et al. (2006 ); Zhang et al. (2006 ). For reported melting-point details, see: Le et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₁ClO₃
M_r = 274.69
Monoclinic, P 2₁ /c
a = 8.1955 (9) Å
b = 10.8717 (12) Å
c = 16.5420 (15) Å
β = 117.816 (4)°
V = 1303.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 296 K
0.34 × 0.19 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.908, T_max = 0.948
11201 measured reflections
4052 independent reflections
2720 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.126
S = 1.03
4052 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Cg2ⁱ	0.97	2.96	3.4952 (17)	116
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681102383X/hb5918sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102383X/hb5918Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681102383X/hb5918Isup3.cml

checkCIF report

Comment top

Phenacyl benzoate derivatives are very important in identification of organic acids (Rather & Reid, 1919) as they undergo photolysis in neutral and mild conditions (Litera et al., 2006). They find applications in the field of synthetic chemistry for the synthesis of oxazoles, imidazoles (Huang et al., 1996) and benzoxazepine (Gandhi et al., 1995). We hereby report the crystal structure of the title compound, (I).

The asymmetric unit of title compound is shown in Fig. 1. The dihedral angle between the phenyl (C10–C15) ring and the chloro-substituted phenyl (C1–C6) ring is 84.29 (8)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those closely related structures (Ogata et al., 1987; Wan et al., 2006; Zhang et al., 2006).

In the crystal (Fig. 2), there are no classical hydrogen bonds but stabilization is provided by weak C—H···π (Table 1) interactions, involving the Cg2 (C10–C15) ring.

Related literature top

For applications of phenacyl benzoate derivatives, see: Rather & Reid (1919); Litera et al. (2006); Huang et al. (1996); Gandhi et al. (1995). For related structures, see: Ogata et al. (1987); Wan et al. (2006); Zhang et al. (2006). For reported melting-point details, see: Le et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of benzoic acid (1.0 g, 0.0081 mol), potassium carbonate (1.23 g, 0.0089 mol) and 2-bromo-1-(4-chlorophenyl) ethanone (1.81 g, 0.0081 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colorless needle-shaped crystals of 2-(4-chlorophenyl)-2-oxoethyl benzoate begin to separate out. These were collected by filtration and recrystallized from ethanol to yield colourless blocks of (I). Yield: 2.10 g, 93.7%, Mp: 119–120 °C (Le et al., 2009).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound (I).

2-(4-Chlorophenyl)-2-oxoethyl benzoate top

Crystal data top

C₁₅H₁₁ClO₃	F(000) = 568
M_r = 274.69	D_x = 1.400 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2797 reflections
a = 8.1955 (9) Å	θ = 2.3–27.1°
b = 10.8717 (12) Å	µ = 0.29 mm⁻¹
c = 16.5420 (15) Å	T = 296 K
β = 117.816 (4)°	Block, colourless
V = 1303.6 (2) Å³	0.34 × 0.19 × 0.19 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4052 independent reflections
Radiation source: fine-focus sealed tube	2720 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 30.8°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.908, T_max = 0.948	k = −15→15
11201 measured reflections	l = −20→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0504P)² + 0.2649P] where P = (F_o² + 2F_c²)/3
4052 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₅H₁₁ClO₃	V = 1303.6 (2) Å³
M_r = 274.69	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1955 (9) Å	µ = 0.29 mm⁻¹
b = 10.8717 (12) Å	T = 296 K
c = 16.5420 (15) Å	0.34 × 0.19 × 0.19 mm
β = 117.816 (4)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4052 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2720 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.948	R_int = 0.021
11201 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
4052 reflections	Δρ_min = −0.49 e Å⁻³
172 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	0.98407 (8)	1.29129 (4)	1.01748 (4)	0.07410 (18)
O1	0.41826 (16)	0.81706 (12)	0.81726 (7)	0.0648 (3)
O2	0.41542 (15)	0.64299 (10)	0.93059 (7)	0.0544 (3)
O3	0.59892 (16)	0.55553 (13)	0.87990 (9)	0.0722 (4)
C1	0.6218 (2)	1.03708 (15)	0.86536 (10)	0.0509 (3)
H1A	0.5394	1.0250	0.8040	0.061*
C2	0.7272 (2)	1.14249 (14)	0.89170 (12)	0.0545 (4)
H2A	0.7170	1.2011	0.8486	0.065*
C3	0.8484 (2)	1.15975 (14)	0.98327 (11)	0.0507 (3)
C4	0.8651 (2)	1.07434 (15)	1.04787 (11)	0.0555 (4)
H4A	0.9469	1.0874	1.1092	0.067*
C5	0.7593 (2)	0.96902 (14)	1.02070 (10)	0.0505 (3)
H5A	0.7701	0.9109	1.0642	0.061*
C6	0.63658 (18)	0.94852 (13)	0.92902 (9)	0.0435 (3)
C7	0.52322 (18)	0.83503 (14)	0.89703 (10)	0.0458 (3)
C8	0.5435 (2)	0.74141 (15)	0.96859 (10)	0.0524 (4)
H8A	0.6680	0.7087	0.9967	0.063*
H8B	0.5243	0.7814	1.0159	0.063*
C9	0.4586 (2)	0.55549 (15)	0.88590 (10)	0.0510 (3)
C10	0.3128 (2)	0.46016 (14)	0.84710 (9)	0.0473 (3)
C11	0.1476 (2)	0.47129 (15)	0.85064 (10)	0.0520 (3)
H11A	0.1261	0.5397	0.8781	0.062*
C12	0.0150 (2)	0.38051 (17)	0.81327 (11)	0.0622 (4)
H12A	−0.0966	0.3888	0.8147	0.075*
C13	0.0468 (3)	0.27865 (18)	0.77419 (12)	0.0688 (5)
H13A	−0.0424	0.2174	0.7498	0.083*
C14	0.2104 (3)	0.26665 (17)	0.77089 (12)	0.0706 (5)
H14A	0.2317	0.1970	0.7445	0.085*
C15	0.3436 (3)	0.35746 (15)	0.80651 (11)	0.0587 (4)
H15A	0.4534	0.3496	0.8032	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0961 (4)	0.0549 (3)	0.0902 (4)	−0.0203 (2)	0.0593 (3)	−0.0167 (2)
O1	0.0575 (7)	0.0764 (8)	0.0440 (6)	−0.0114 (6)	0.0100 (5)	0.0018 (5)
O2	0.0573 (6)	0.0533 (6)	0.0590 (6)	−0.0116 (5)	0.0325 (5)	−0.0065 (5)
O3	0.0551 (7)	0.0808 (9)	0.0885 (9)	−0.0061 (6)	0.0399 (7)	−0.0124 (7)
C1	0.0525 (8)	0.0567 (9)	0.0423 (7)	0.0060 (7)	0.0212 (6)	0.0066 (6)
C2	0.0646 (9)	0.0483 (8)	0.0593 (9)	0.0064 (7)	0.0361 (8)	0.0109 (7)
C3	0.0559 (8)	0.0453 (7)	0.0615 (9)	−0.0017 (6)	0.0362 (7)	−0.0066 (7)
C4	0.0624 (9)	0.0564 (9)	0.0471 (8)	−0.0057 (7)	0.0251 (7)	−0.0062 (7)
C5	0.0583 (8)	0.0518 (8)	0.0404 (7)	−0.0027 (7)	0.0222 (6)	0.0035 (6)
C6	0.0434 (7)	0.0475 (7)	0.0411 (7)	0.0036 (6)	0.0210 (6)	0.0020 (6)
C7	0.0404 (7)	0.0535 (8)	0.0419 (7)	0.0010 (6)	0.0179 (6)	0.0008 (6)
C8	0.0554 (8)	0.0541 (8)	0.0462 (8)	−0.0102 (7)	0.0224 (7)	−0.0010 (7)
C9	0.0506 (8)	0.0537 (8)	0.0485 (8)	0.0010 (7)	0.0229 (7)	0.0053 (7)
C10	0.0526 (8)	0.0463 (7)	0.0405 (7)	0.0016 (6)	0.0196 (6)	0.0066 (6)
C11	0.0545 (8)	0.0520 (8)	0.0486 (8)	−0.0029 (7)	0.0233 (7)	0.0030 (7)
C12	0.0579 (9)	0.0679 (10)	0.0539 (9)	−0.0110 (8)	0.0203 (8)	0.0042 (8)
C13	0.0739 (12)	0.0609 (10)	0.0541 (10)	−0.0154 (9)	0.0151 (9)	0.0009 (8)
C14	0.0960 (14)	0.0496 (9)	0.0526 (10)	0.0016 (9)	0.0233 (10)	−0.0037 (8)
C15	0.0692 (10)	0.0547 (9)	0.0520 (9)	0.0092 (8)	0.0282 (8)	0.0051 (7)

Geometric parameters (Å, º) top

Cl1—C3	1.7362 (16)	C7—C8	1.510 (2)
O1—C7	1.2083 (17)	C8—H8A	0.9700
O2—C9	1.3492 (19)	C8—H8B	0.9700
O2—C8	1.4235 (18)	C9—C10	1.482 (2)
O3—C9	1.1996 (18)	C10—C15	1.385 (2)
C1—C2	1.378 (2)	C10—C11	1.388 (2)
C1—C6	1.390 (2)	C11—C12	1.382 (2)
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.383 (2)	C12—C13	1.367 (3)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.373 (2)	C13—C14	1.373 (3)
C4—C5	1.379 (2)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.384 (3)
C5—C6	1.3920 (19)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.486 (2)

C9—O2—C8	116.36 (12)	O2—C8—H8B	109.3
C2—C1—C6	121.10 (14)	C7—C8—H8B	109.3
C2—C1—H1A	119.5	H8A—C8—H8B	107.9
C6—C1—H1A	119.5	O3—C9—O2	123.48 (15)
C1—C2—C3	118.90 (14)	O3—C9—C10	125.06 (15)
C1—C2—H2A	120.6	O2—C9—C10	111.46 (13)
C3—C2—H2A	120.6	C15—C10—C11	119.52 (15)
C4—C3—C2	121.36 (15)	C15—C10—C9	118.75 (14)
C4—C3—Cl1	119.15 (13)	C11—C10—C9	121.72 (14)
C2—C3—Cl1	119.49 (13)	C12—C11—C10	119.86 (16)
C3—C4—C5	119.25 (15)	C12—C11—H11A	120.1
C3—C4—H4A	120.4	C10—C11—H11A	120.1
C5—C4—H4A	120.4	C13—C12—C11	120.41 (18)
C4—C5—C6	120.85 (14)	C13—C12—H12A	119.8
C4—C5—H5A	119.6	C11—C12—H12A	119.8
C6—C5—H5A	119.6	C12—C13—C14	120.06 (17)
C1—C6—C5	118.54 (14)	C12—C13—H13A	120.0
C1—C6—C7	119.12 (13)	C14—C13—H13A	120.0
C5—C6—C7	122.34 (13)	C13—C14—C15	120.43 (17)
O1—C7—C6	122.11 (14)	C13—C14—H14A	119.8
O1—C7—C8	120.59 (14)	C15—C14—H14A	119.8
C6—C7—C8	117.30 (12)	C14—C15—C10	119.69 (17)
O2—C8—C7	111.81 (12)	C14—C15—H15A	120.2
O2—C8—H8A	109.3	C10—C15—H15A	120.2
C7—C8—H8A	109.3

C6—C1—C2—C3	−0.4 (2)	C6—C7—C8—O2	174.36 (12)
C1—C2—C3—C4	−0.1 (2)	C8—O2—C9—O3	2.5 (2)
C1—C2—C3—Cl1	179.31 (11)	C8—O2—C9—C10	−178.30 (12)
C2—C3—C4—C5	0.3 (2)	O3—C9—C10—C15	5.2 (2)
Cl1—C3—C4—C5	−179.14 (12)	O2—C9—C10—C15	−173.94 (13)
C3—C4—C5—C6	0.0 (2)	O3—C9—C10—C11	−174.87 (16)
C2—C1—C6—C5	0.7 (2)	O2—C9—C10—C11	5.9 (2)
C2—C1—C6—C7	−178.58 (13)	C15—C10—C11—C12	−0.4 (2)
C4—C5—C6—C1	−0.5 (2)	C9—C10—C11—C12	179.72 (14)
C4—C5—C6—C7	178.73 (14)	C10—C11—C12—C13	1.1 (2)
C1—C6—C7—O1	0.0 (2)	C11—C12—C13—C14	−0.8 (3)
C5—C6—C7—O1	−179.21 (15)	C12—C13—C14—C15	−0.3 (3)
C1—C6—C7—C8	−179.92 (13)	C13—C14—C15—C10	1.1 (3)
C5—C6—C7—C8	0.9 (2)	C11—C10—C15—C14	−0.7 (2)
C9—O2—C8—C7	79.04 (17)	C9—C10—C15—C14	179.19 (15)
O1—C7—C8—O2	−5.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Cg2ⁱ	0.97	2.96	3.4952 (17)	116

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁ClO₃
M_r	274.69
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.1955 (9), 10.8717 (12), 16.5420 (15)
β (°)	117.816 (4)
V (Å³)	1303.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.34 × 0.19 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.908, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	11201, 4052, 2720
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.721

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.126, 1.03
No. of reflections	4052
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.49

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Cg2ⁱ	0.97	2.96	3.4952 (17)	116

Symmetry code: (i) −x+1, −y+1, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship. AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India for the Young Scientist award. GB thanks the Department of Information Technology, New Delhi, India, for financial support.

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1802

doi:10.1107/S160053681102383X

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