2-Oxo-2-phenyl­ethyl benzoate

Fun, H.-K.; Arshad, S.; Garudachari, B.; Isloor, A.M.; Satyanarayan, M.N.

doi:10.1107/S1600536811018976

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1528

doi:10.1107/S1600536811018976

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2-Oxo-2-phenylethyl benzoate

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^a B. Garudachari,^b Arun M. Isloor ^b and M. N. Satyanarayan ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bOrganic Chemistry 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 16 May 2011; accepted 19 May 2011; online 25 May 2011)

In the title compound, C₁₅H₁₂O₃, the terminal phenyl rings make a dihedral angle of 86.09 (9)° with each other. In the crystal, a pair of intermolecular C—H⋯O hydrogen bonds link the molecules, forming a dimer with an R₂²(10) ring motif.

Related literature

For background to and applications of phenacyl benzoates, see: Huang et al. (1996 ); Gandhi et al. (1995 ); Ruzicka et al. (2002 ); Litera et al. (2006 ); Sheehan & Umezaw (1973 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₂O₃
M_r = 240.25
Monoclinic, P 2₁ /c
a = 9.0299 (13) Å
b = 14.116 (2) Å
c = 9.6379 (14) Å
β = 90.564 (3)°
V = 1228.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.77 × 0.52 × 0.43 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.934, T_max = 0.963
23225 measured reflections
3573 independent reflections
2408 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.192
S = 1.05
3573 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O3ⁱ	0.97	2.57	3.454 (2)	152
Symmetry code: (i) -x+1, -y, -z+1.

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/S1600536811018976/is2715sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018976/is2715Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018976/is2715Isup3.cml

checkCIF report

Comment top

In organic chemistry, phenacyl benzoate is a derivative of an acid, formed by reaction between acid and phenacyl bromide. They find applications in the field of synthetic chemistry (Huang et al., 1996; Gandhi et al., 1995) such as synthesis of oxazoles, imidazoles, benzoxazepines. They are also useful for photo-removable protecting groups for carboxylic acids in organic synthesis and biochemistry (Ruzicka et al., 2002; Litera et al., 2006; Sheehan & Umezaw, 1973). Keeping this in view, the title compound was synthesized to study its crystal structure.

The molecular structure is shown in Fig. 1. The terminal phenyl rings (C1–C6 and C10–C15) make a dihedral angle of 86.09 (9)° with each other. Bond lengths (Allen et al., 1987) and angles are within normal range. In the crystal packing (Fig. 2), pairs of intermolecular C8—H8B···O3 hydrogen bonds (Table 1) link the molecules to form dimers, generating R²₂(10) ring motifs (Bernstein et al., 1995).

Related literature top

For background to and applications of phenacyl benzoates, see: Huang et al. (1996); Gandhi et al. (1995); Ruzicka et al. (2002); Litera et al. (2006); Sheehan & Umezaw (1973). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The mixture of benzoic acid (1.0 g, 0.008 mol), sodium carbonate (0.95 g, 0.009 mol) and 2-bromo-1-phenylethanon (1.7 g, 0.009 mol) in dimethyl formamide (10 ml) was stirred at room temperature for 2 h. On cooling, the separated colourless needle-shaped crystals of 2-oxo-2-phenylethyl benzoate were collected by filtration. Compound was recrystallized from ethanol (yield: 1.91 g, 97.4%; m.p: 390–391 K).

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 and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound. Dashed lines represent the hydrogen bonds.

2-Oxo-2-phenylethyl benzoate top

Crystal data top

C₁₅H₁₂O₃	F(000) = 504
M_r = 240.25	D_x = 1.299 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6650 reflections
a = 9.0299 (13) Å	θ = 2.6–29.6°
b = 14.116 (2) Å	µ = 0.09 mm⁻¹
c = 9.6379 (14) Å	T = 296 K
β = 90.564 (3)°	Block, colourless
V = 1228.4 (3) Å³	0.77 × 0.52 × 0.43 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	3573 independent reflections
Radiation source: fine-focus sealed tube	2408 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.934, T_max = 0.963	k = −19→19
23225 measured reflections	l = −13→13

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0845P)² + 0.258P] where P = (F_o² + 2F_c²)/3
3573 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₂O₃	V = 1228.4 (3) Å³
M_r = 240.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0299 (13) Å	µ = 0.09 mm⁻¹
b = 14.116 (2) Å	T = 296 K
c = 9.6379 (14) Å	0.77 × 0.52 × 0.43 mm
β = 90.564 (3)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	3573 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2408 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.963	R_int = 0.035
23225 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.192	H-atom parameters constrained
S = 1.05	Δρ_max = 0.25 e Å⁻³
3573 reflections	Δρ_min = −0.19 e Å⁻³
163 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
O1	0.89801 (19)	0.00806 (10)	0.7007 (2)	0.0993 (6)
O2	0.75397 (14)	0.10379 (9)	0.50588 (15)	0.0704 (4)
O3	0.56279 (16)	0.08421 (9)	0.64940 (17)	0.0813 (4)
C1	0.7648 (2)	−0.20439 (12)	0.5344 (2)	0.0647 (4)
H1A	0.6994	−0.1779	0.4702	0.078*
C2	0.7776 (3)	−0.30148 (14)	0.5449 (2)	0.0790 (6)
H2A	0.7197	−0.3403	0.4884	0.095*
C3	0.8752 (2)	−0.34132 (13)	0.6386 (2)	0.0751 (5)
H3A	0.8843	−0.4068	0.6443	0.090*
C4	0.9593 (2)	−0.28413 (15)	0.7237 (2)	0.0762 (5)
H4A	1.0248	−0.3110	0.7876	0.091*
C5	0.9467 (2)	−0.18735 (13)	0.7146 (2)	0.0693 (5)
H5A	1.0037	−0.1490	0.7726	0.083*
C6	0.84954 (16)	−0.14632 (11)	0.61946 (17)	0.0544 (4)
C7	0.84060 (17)	−0.04164 (12)	0.6139 (2)	0.0602 (4)
C8	0.7618 (2)	0.00214 (13)	0.4948 (2)	0.0642 (4)
H8A	0.8123	−0.0145	0.4098	0.077*
H8B	0.6621	−0.0233	0.4891	0.077*
C9	0.64689 (17)	0.13613 (11)	0.59154 (17)	0.0548 (4)
C10	0.64216 (16)	0.24087 (11)	0.60075 (17)	0.0524 (4)
C11	0.7258 (2)	0.29780 (13)	0.5158 (2)	0.0693 (5)
H11A	0.7899	0.2708	0.4520	0.083*
C12	0.7138 (3)	0.39614 (14)	0.5260 (3)	0.0826 (6)
H12A	0.7692	0.4350	0.4683	0.099*
C13	0.6201 (2)	0.43540 (13)	0.6216 (2)	0.0772 (6)
H13A	0.6122	0.5009	0.6284	0.093*
C14	0.5385 (2)	0.37905 (14)	0.7064 (2)	0.0760 (5)
H14A	0.4760	0.4063	0.7713	0.091*
C15	0.5483 (2)	0.28147 (13)	0.6964 (2)	0.0659 (5)
H15A	0.4919	0.2432	0.7540	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1077 (11)	0.0599 (8)	0.1294 (13)	0.0017 (8)	−0.0530 (10)	−0.0200 (8)
O2	0.0689 (8)	0.0530 (7)	0.0896 (9)	0.0013 (5)	0.0084 (7)	0.0022 (6)
O3	0.0744 (8)	0.0530 (7)	0.1171 (12)	−0.0103 (6)	0.0231 (8)	0.0051 (7)
C1	0.0653 (10)	0.0523 (9)	0.0764 (11)	−0.0002 (7)	−0.0094 (8)	−0.0014 (8)
C2	0.0890 (14)	0.0553 (10)	0.0924 (14)	−0.0088 (9)	−0.0098 (11)	−0.0055 (9)
C3	0.0767 (12)	0.0514 (9)	0.0975 (14)	0.0015 (8)	0.0076 (10)	0.0079 (9)
C4	0.0682 (11)	0.0654 (11)	0.0948 (14)	0.0087 (9)	−0.0041 (10)	0.0141 (10)
C5	0.0603 (10)	0.0634 (11)	0.0841 (12)	0.0002 (8)	−0.0104 (9)	0.0002 (9)
C6	0.0460 (7)	0.0506 (8)	0.0668 (9)	0.0018 (6)	0.0047 (6)	−0.0028 (7)
C7	0.0478 (8)	0.0516 (8)	0.0811 (11)	0.0003 (6)	−0.0023 (7)	−0.0079 (8)
C8	0.0620 (9)	0.0524 (9)	0.0780 (11)	0.0042 (7)	−0.0026 (8)	−0.0127 (8)
C9	0.0485 (8)	0.0484 (8)	0.0675 (9)	−0.0030 (6)	−0.0033 (7)	0.0011 (7)
C10	0.0481 (7)	0.0459 (8)	0.0629 (9)	−0.0010 (6)	−0.0074 (6)	0.0018 (6)
C11	0.0770 (12)	0.0556 (10)	0.0753 (11)	−0.0033 (8)	0.0097 (9)	0.0039 (8)
C12	0.1004 (15)	0.0544 (10)	0.0930 (14)	−0.0110 (10)	0.0040 (12)	0.0145 (10)
C13	0.0865 (13)	0.0464 (9)	0.0985 (15)	0.0037 (9)	−0.0135 (11)	−0.0027 (9)
C14	0.0737 (12)	0.0592 (10)	0.0953 (14)	0.0071 (9)	0.0016 (10)	−0.0154 (10)
C15	0.0623 (10)	0.0577 (9)	0.0776 (11)	−0.0023 (8)	0.0048 (8)	−0.0036 (8)

Geometric parameters (Å, º) top

O1—C7	1.205 (2)	C7—C8	1.481 (3)
O2—C9	1.357 (2)	C8—H8A	0.9700
O2—C8	1.441 (2)	C8—H8B	0.9700
O3—C9	1.197 (2)	C9—C10	1.482 (2)
C1—C2	1.379 (3)	C10—C11	1.378 (2)
C1—C6	1.385 (2)	C10—C15	1.383 (2)
C1—H1A	0.9300	C11—C12	1.396 (3)
C2—C3	1.376 (3)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.374 (3)
C3—C4	1.375 (3)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.362 (3)
C4—C5	1.374 (3)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.384 (3)
C5—C6	1.389 (2)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.481 (2)

C9—O2—C8	114.58 (13)	O2—C8—H8B	109.1
C2—C1—C6	119.97 (17)	C7—C8—H8B	109.1
C2—C1—H1A	120.0	H8A—C8—H8B	107.9
C6—C1—H1A	120.0	O3—C9—O2	122.46 (15)
C3—C2—C1	120.47 (19)	O3—C9—C10	124.34 (15)
C3—C2—H2A	119.8	O2—C9—C10	113.16 (13)
C1—C2—H2A	119.8	C11—C10—C15	119.85 (16)
C4—C3—C2	119.89 (18)	C11—C10—C9	121.99 (15)
C4—C3—H3A	120.1	C15—C10—C9	118.15 (15)
C2—C3—H3A	120.1	C10—C11—C12	119.62 (19)
C5—C4—C3	120.06 (19)	C10—C11—H11A	120.2
C5—C4—H4A	120.0	C12—C11—H11A	120.2
C3—C4—H4A	120.0	C13—C12—C11	119.83 (19)
C4—C5—C6	120.55 (18)	C13—C12—H12A	120.1
C4—C5—H5A	119.7	C11—C12—H12A	120.1
C6—C5—H5A	119.7	C14—C13—C12	120.46 (18)
C1—C6—C5	119.05 (16)	C14—C13—H13A	119.8
C1—C6—C7	122.68 (15)	C12—C13—H13A	119.8
C5—C6—C7	118.27 (15)	C13—C14—C15	120.29 (19)
O1—C7—C8	119.72 (16)	C13—C14—H14A	119.9
O1—C7—C6	122.22 (17)	C15—C14—H14A	119.9
C8—C7—C6	118.04 (14)	C10—C15—C14	119.94 (18)
O2—C8—C7	112.43 (14)	C10—C15—H15A	120.0
O2—C8—H8A	109.1	C14—C15—H15A	120.0
C7—C8—H8A	109.1

C6—C1—C2—C3	−0.7 (3)	C8—O2—C9—O3	−2.3 (2)
C1—C2—C3—C4	0.9 (3)	C8—O2—C9—C10	179.89 (14)
C2—C3—C4—C5	−0.5 (3)	O3—C9—C10—C11	−169.63 (18)
C3—C4—C5—C6	−0.2 (3)	O2—C9—C10—C11	8.1 (2)
C2—C1—C6—C5	0.0 (3)	O3—C9—C10—C15	9.2 (3)
C2—C1—C6—C7	−179.66 (17)	O2—C9—C10—C15	−173.09 (14)
C4—C5—C6—C1	0.4 (3)	C15—C10—C11—C12	−0.7 (3)
C4—C5—C6—C7	−179.90 (18)	C9—C10—C11—C12	178.10 (18)
C1—C6—C7—O1	169.12 (19)	C10—C11—C12—C13	0.7 (3)
C5—C6—C7—O1	−10.6 (3)	C11—C12—C13—C14	−0.1 (3)
C1—C6—C7—C8	−12.7 (2)	C12—C13—C14—C15	−0.6 (3)
C5—C6—C7—C8	167.58 (16)	C11—C10—C15—C14	0.1 (3)
C9—O2—C8—C7	−79.71 (18)	C9—C10—C15—C14	−178.74 (16)
O1—C7—C8—O2	−5.0 (2)	C13—C14—C15—C10	0.5 (3)
C6—C7—C8—O2	176.76 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O3ⁱ	0.97	2.57	3.454 (2)	152

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂O₃
M_r	240.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.0299 (13), 14.116 (2), 9.6379 (14)
β (°)	90.564 (3)
V (Å³)	1228.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.77 × 0.52 × 0.43

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.934, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	23225, 3573, 2408
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.192, 1.05
No. of reflections	3573
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.19

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O3ⁱ	0.97	2.57	3.454 (2)	152

Symmetry code: (i) −x+1, −y, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India for a `Young scientist' award. GB thanks the Department of Information Technology, New Delhi, India, for financial support.

References

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