2-(4-Methyl-phen-yl)-2-oxoethyl 3-bromo-benzoate.

The mol-ecule of the title compound, C16H13BrO3, is built of two approximately planar fragments, viz. 3-bromo-benzoate [maximum deviation = 0.055 (2) Å and 2-oxo-2-p-tolyl-ethyl [maximum deviation = 0.042 (2) Å], inclined by 46.51 (7)°. In the crystal, weak C-H⋯O hydrogen bonds and Br⋯Br contacts [3.6491 (7) Å] connect the mol-ecules into infinite layers parallel to (-221).

Related literature

For the structures of similar compounds, see: Fun, Arshad et al. (2011 ▶); Fun, Loh et al. (2011 ▶); Fun, Ooi et al. (2011 ▶); Fun, Shahani et al. (2011 ▶).

Experimental

Crystal data

C16H13BrO3

M = 333.17

Triclinic,

a = 4.7977 (3) Å

b = 10.9951 (7) Å

c = 14.1645 (8) Å

α = 74.829 (5)°

β = 87.758 (5)°

γ = 79.327 (5)°

V = 708.64 (7) Å3

Z = 2

Mo Kα radiation

μ = 2.90 mm−1

T = 295 K

0.25 × 0.2 × 0.08 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.335, T max = 1.000

7924 measured reflections

2501 independent reflections

1768 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.05

2501 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046995/ng5304sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046995/ng5304Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046995/ng5304Isup3.cml

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

C16H13BrO3	Z = 2
Mr = 333.17	F(000) = 336
Triclinic, P1	Dx = 1.561 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7977 (3) Å	Cell parameters from 2186 reflections
b = 10.9951 (7) Å	θ = 3.0–29.0°
c = 14.1645 (8) Å	µ = 2.90 mm−1
α = 74.829 (5)°	T = 295 K
β = 87.758 (5)°	Plate, colourless
γ = 79.327 (5)°	0.25 × 0.2 × 0.08 mm
V = 708.64 (7) Å3

Agilent Xcalibur Eos diffractometer	2501 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1768 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 16.1544 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω–scan	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→13
Tmin = 0.335, Tmax = 1.000	l = −16→16
7924 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.053P)2 + 0.0904P] where P = (Fo2 + 2Fc2)/3
2501 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	−0.0123 (5)	0.2958 (2)	0.3969 (2)	0.0458 (6)
C2	−0.0749 (6)	0.3618 (3)	0.3014 (2)	0.0526 (7)
H2	−0.0098	0.4380	0.2744	0.049 (8)*
C3	−0.2350 (6)	0.3141 (3)	0.2459 (2)	0.0600 (8)
Br3	−0.32035 (10)	0.40451 (4)	0.11376 (3)	0.1043 (2)
C4	−0.3331 (7)	0.2016 (3)	0.2848 (3)	0.0694 (9)
H4	−0.4406	0.1701	0.2467	0.079 (10)*
C5	−0.2713 (7)	0.1369 (3)	0.3799 (3)	0.0715 (9)
H5	−0.3383	0.0612	0.4067	0.088 (12)*
C6	−0.1099 (6)	0.1829 (3)	0.4368 (2)	0.0576 (7)
H6	−0.0674	0.1381	0.5015	0.069 (9)*
C7	0.1605 (6)	0.3501 (3)	0.4556 (2)	0.0473 (7)
O7	0.2638 (5)	0.4429 (2)	0.42375 (15)	0.0679 (6)
O8	0.1859 (5)	0.2813 (2)	0.54790 (14)	0.0658 (6)
C9	0.3630 (7)	0.3139 (3)	0.6129 (2)	0.0609 (8)
H91	0.2473	0.3539	0.6581	0.081 (11)*
H92	0.4775	0.3739	0.5760	0.071 (10)*
C10	0.5507 (6)	0.1933 (3)	0.6681 (2)	0.0524 (7)
O10	0.5558 (5)	0.0932 (2)	0.64683 (19)	0.0828 (7)
C11	0.7323 (6)	0.1995 (3)	0.74883 (19)	0.0492 (7)
C12	0.9153 (7)	0.0901 (3)	0.7958 (2)	0.0662 (8)
H12	0.9238	0.0154	0.7758	0.084 (11)*
C13	1.0847 (7)	0.0896 (3)	0.8713 (3)	0.0729 (9)
H13	1.2053	0.0143	0.9022	0.090 (11)*
C14	1.0804 (6)	0.1984 (3)	0.9026 (2)	0.0621 (8)
C141	1.2672 (8)	0.1975 (4)	0.9864 (3)	0.0861 (11)
H14A	1.2630	0.2839	0.9899	0.129*
H14B	1.4583	0.1588	0.9760	0.129*
H14C	1.1988	0.1493	1.0466	0.129*
C15	0.8999 (7)	0.3084 (3)	0.8553 (2)	0.0625 (8)
H15	0.8935	0.3831	0.8751	0.087 (12)*
C16	0.7272 (6)	0.3098 (3)	0.7786 (2)	0.0567 (8)
H16	0.6078	0.3852	0.7471	0.057 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0446 (15)	0.0450 (15)	0.0505 (16)	−0.0089 (12)	−0.0063 (12)	−0.0156 (12)
C2	0.0567 (17)	0.0521 (17)	0.0504 (16)	−0.0082 (13)	−0.0129 (13)	−0.0148 (13)
C3	0.0624 (19)	0.0616 (19)	0.0565 (18)	0.0044 (15)	−0.0214 (14)	−0.0239 (15)
Br3	0.1370 (4)	0.1121 (4)	0.0632 (3)	−0.0071 (3)	−0.0476 (2)	−0.0254 (2)
C4	0.063 (2)	0.070 (2)	0.086 (2)	−0.0042 (16)	−0.0257 (17)	−0.0422 (19)
C5	0.076 (2)	0.0570 (19)	0.089 (3)	−0.0188 (16)	−0.0179 (19)	−0.0251 (18)
C6	0.0611 (19)	0.0512 (17)	0.0621 (19)	−0.0100 (14)	−0.0132 (14)	−0.0155 (15)
C7	0.0496 (16)	0.0497 (16)	0.0443 (15)	−0.0114 (13)	−0.0086 (12)	−0.0124 (13)
O7	0.0873 (16)	0.0654 (13)	0.0551 (12)	−0.0380 (12)	−0.0191 (11)	−0.0034 (10)
O8	0.0865 (15)	0.0708 (13)	0.0456 (12)	−0.0411 (11)	−0.0199 (10)	−0.0032 (10)
C9	0.077 (2)	0.0640 (18)	0.0477 (17)	−0.0278 (16)	−0.0182 (16)	−0.0116 (15)
C10	0.0626 (18)	0.0583 (18)	0.0428 (15)	−0.0261 (14)	0.0009 (13)	−0.0140 (13)
O10	0.1036 (18)	0.0669 (14)	0.0898 (17)	−0.0245 (13)	−0.0233 (14)	−0.0314 (13)
C11	0.0514 (17)	0.0560 (16)	0.0409 (15)	−0.0174 (13)	−0.0016 (12)	−0.0080 (13)
C12	0.067 (2)	0.0602 (19)	0.071 (2)	−0.0069 (15)	−0.0087 (17)	−0.0184 (16)
C13	0.061 (2)	0.074 (2)	0.075 (2)	0.0002 (17)	−0.0183 (17)	−0.0108 (18)
C14	0.0527 (18)	0.085 (2)	0.0456 (16)	−0.0219 (16)	−0.0094 (13)	−0.0029 (16)
C141	0.072 (2)	0.114 (3)	0.068 (2)	−0.025 (2)	−0.0261 (18)	−0.006 (2)
C15	0.071 (2)	0.071 (2)	0.0503 (17)	−0.0276 (16)	−0.0097 (15)	−0.0121 (15)
C16	0.069 (2)	0.0532 (17)	0.0463 (16)	−0.0164 (14)	−0.0158 (14)	−0.0035 (14)

C1—C2	1.372 (4)	C9—H92	0.9700
C1—C6	1.382 (4)	C10—O10	1.210 (4)
C1—C7	1.494 (4)	C10—C11	1.488 (4)
C2—C3	1.376 (4)	C11—C12	1.378 (4)
C2—H2	0.9300	C11—C16	1.379 (4)
C3—C4	1.376 (5)	C12—C13	1.367 (5)
C3—Br3	1.895 (3)	C12—H12	0.9300
C4—C5	1.364 (5)	C13—C14	1.376 (5)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.382 (4)	C14—C15	1.377 (4)
C5—H5	0.9300	C14—C141	1.512 (4)
C6—H6	0.9300	C141—H14A	0.9600
C7—O7	1.191 (3)	C141—H14B	0.9600
C7—O8	1.325 (3)	C141—H14C	0.9600
O8—C9	1.430 (3)	C15—C16	1.387 (4)
C9—C10	1.501 (4)	C15—H15	0.9300
C9—H91	0.9700	C16—H16	0.9300
C2—C1—C6	120.2 (3)	O10—C10—C11	120.7 (3)
C2—C1—C7	118.2 (2)	O10—C10—C9	120.7 (3)
C6—C1—C7	121.5 (2)	C11—C10—C9	118.6 (3)
C1—C2—C3	119.4 (3)	C12—C11—C16	118.4 (3)
C1—C2—H2	120.3	C12—C11—C10	118.4 (3)
C3—C2—H2	120.3	C16—C11—C10	123.2 (3)
C4—C3—C2	120.9 (3)	C13—C12—C11	121.0 (3)
C4—C3—Br3	119.6 (2)	C13—C12—H12	119.5
C2—C3—Br3	119.5 (2)	C11—C12—H12	119.5
C5—C4—C3	119.4 (3)	C12—C13—C14	121.4 (3)
C5—C4—H4	120.3	C12—C13—H13	119.3
C3—C4—H4	120.3	C14—C13—H13	119.3
C4—C5—C6	120.6 (3)	C13—C14—C15	117.9 (3)
C4—C5—H5	119.7	C13—C14—C141	121.3 (3)
C6—C5—H5	119.7	C15—C14—C141	120.9 (3)
C1—C6—C5	119.5 (3)	C14—C141—H14A	109.5
C1—C6—H6	120.3	C14—C141—H14B	109.5
C5—C6—H6	120.3	H14A—C141—H14B	109.5
O7—C7—O8	124.1 (3)	C14—C141—H14C	109.5
O7—C7—C1	124.5 (2)	H14A—C141—H14C	109.5
O8—C7—C1	111.3 (2)	H14B—C141—H14C	109.5
C7—O8—C9	118.8 (2)	C14—C15—C16	121.2 (3)
O8—C9—C10	108.3 (2)	C14—C15—H15	119.4
O8—C9—H91	110.0	C16—C15—H15	119.4
C10—C9—H91	110.0	C11—C16—C15	120.1 (3)
O8—C9—H92	110.0	C11—C16—H16	119.9
C10—C9—H92	110.0	C15—C16—H16	119.9
H91—C9—H92	108.4
C6—C1—C2—C3	−0.2 (4)	O8—C9—C10—O10	7.5 (4)
C7—C1—C2—C3	−179.7 (2)	O8—C9—C10—C11	−173.0 (2)
C1—C2—C3—C4	0.1 (4)	O10—C10—C11—C12	2.9 (4)
C1—C2—C3—Br3	−179.7 (2)	C9—C10—C11—C12	−176.6 (3)
C2—C3—C4—C5	0.2 (5)	O10—C10—C11—C16	−177.5 (3)
Br3—C3—C4—C5	−180.0 (2)	C9—C10—C11—C16	3.1 (4)
C3—C4—C5—C6	−0.5 (5)	C16—C11—C12—C13	1.2 (5)
C2—C1—C6—C5	−0.1 (4)	C10—C11—C12—C13	−179.2 (3)
C7—C1—C6—C5	179.4 (3)	C11—C12—C13—C14	−0.5 (5)
C4—C5—C6—C1	0.4 (5)	C12—C13—C14—C15	−0.1 (5)
C2—C1—C7—O7	−5.0 (4)	C12—C13—C14—C141	179.8 (3)
C6—C1—C7—O7	175.5 (3)	C13—C14—C15—C16	0.1 (5)
C2—C1—C7—O8	175.4 (2)	C141—C14—C15—C16	−179.8 (3)
C6—C1—C7—O8	−4.1 (4)	C12—C11—C16—C15	−1.2 (4)
O7—C7—O8—C9	−4.4 (4)	C10—C11—C16—C15	179.2 (3)
C1—C7—O8—C9	175.2 (2)	C14—C15—C16—C11	0.5 (5)
C7—O8—C9—C10	−132.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O10i	0.93	2.44	3.198 (4)	139
C9—H92···O7ii	0.97	2.56	3.406 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O10i	0.93	2.44	3.198 (4)	139
C9—H92⋯O7ii	0.97	2.56	3.406 (4)	146

Symmetry codes: (i) ; (ii) .