2-(4-Bromo-phen-yl)-2-oxoethyl 2-meth-oxy-benzoate.

In the title mol-ecule, C(16)H(13)BrO(4), the dihedral angle between the benzene rings is 85.92 (10)°. In the crystal, mol-ecules are linked into chains along [100] via weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to and applications of phenacyl benzoate derivatives, see: Rather & Reid (1919 ▶); Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶); Huang et al. (1996 ▶); Gandhi et al. (1995 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13BrO4

M = 349.17

Orthorhombic,

a = 7.8424 (5) Å

b = 14.6799 (9) Å

c = 25.7677 (14) Å

V = 2966.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 2.78 mm−1

T = 296 K

0.56 × 0.25 × 0.12 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.306, T max = 0.733

19358 measured reflections

4731 independent reflections

2916 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.00

4731 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.54 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023002/lh5263sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023002/lh5263Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023002/lh5263Isup3.cml

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

C16H13BrO4	F(000) = 1408
Mr = 349.17	Dx = 1.564 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3938 reflections
a = 7.8424 (5) Å	θ = 2.8–26.5°
b = 14.6799 (9) Å	µ = 2.78 mm−1
c = 25.7677 (14) Å	T = 296 K
V = 2966.5 (3) Å3	Needle, colourless
Z = 8	0.56 × 0.25 × 0.12 mm

Bruker SMART APEXII DUO CCD area-detector diffractometer	4731 independent reflections
Radiation source: fine-focus sealed tube	2916 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 31.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.306, Tmax = 0.733	k = −21→14
19358 measured reflections	l = −37→37

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0329P)2 + 1.2401P] where P = (Fo2 + 2Fc2)/3
4731 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	1.19995 (4)	0.063553 (17)	0.603716 (11)	0.07024 (11)
O1	0.4583 (2)	0.13020 (14)	0.46925 (7)	0.0717 (5)
O2	0.4899 (2)	0.19606 (9)	0.37415 (6)	0.0579 (4)
O3	0.4628 (2)	0.04790 (10)	0.35626 (6)	0.0604 (4)
O4	0.19571 (19)	0.00663 (10)	0.29651 (6)	0.0544 (4)
C1	0.9183 (3)	0.14467 (14)	0.47702 (8)	0.0488 (5)
H1A	0.9406	0.1695	0.4445	0.059*
C2	1.0517 (3)	0.12695 (15)	0.51036 (8)	0.0517 (5)
H2A	1.1635	0.1396	0.5007	0.062*
C3	1.0158 (3)	0.09006 (13)	0.55825 (8)	0.0487 (5)
C4	0.8516 (3)	0.07055 (14)	0.57344 (8)	0.0538 (5)
H4A	0.8302	0.0457	0.6060	0.065*
C5	0.7199 (3)	0.08825 (15)	0.53991 (8)	0.0504 (5)
H5A	0.6087	0.0749	0.5498	0.060*
C6	0.7504 (3)	0.12584 (13)	0.49133 (7)	0.0428 (4)
C7	0.6034 (3)	0.14284 (14)	0.45588 (8)	0.0470 (4)
C8	0.6423 (3)	0.17663 (14)	0.40202 (8)	0.0496 (5)
H8A	0.7113	0.2313	0.4042	0.059*
H8B	0.7073	0.1308	0.3835	0.059*
C9	0.4043 (3)	0.12319 (13)	0.35557 (7)	0.0444 (4)
C10	0.2356 (3)	0.15108 (13)	0.33476 (7)	0.0420 (4)
C11	0.1753 (3)	0.23898 (15)	0.34381 (8)	0.0540 (5)
H11A	0.2411	0.2790	0.3633	0.065*
C12	0.0207 (3)	0.26793 (17)	0.32457 (9)	0.0654 (6)
H12A	−0.0176	0.3268	0.3311	0.078*
C13	−0.0762 (3)	0.20873 (18)	0.29561 (9)	0.0643 (6)
H13A	−0.1803	0.2280	0.2823	0.077*
C14	−0.0216 (3)	0.12187 (16)	0.28619 (8)	0.0551 (5)
H14A	−0.0894	0.0827	0.2668	0.066*
C15	0.1337 (3)	0.09149 (13)	0.30522 (7)	0.0442 (4)
C16	0.0967 (4)	−0.05475 (17)	0.26574 (11)	0.0735 (7)
H16A	0.1556	−0.1118	0.2627	0.110*
H16B	0.0799	−0.0292	0.2318	0.110*
H16C	−0.0120	−0.0644	0.2820	0.110*

	U11	U22	U33	U12	U13	U23
Br1	0.07526 (19)	0.05554 (15)	0.07991 (18)	0.00639 (12)	−0.03345 (13)	−0.00558 (11)
O1	0.0385 (8)	0.1055 (14)	0.0713 (10)	−0.0059 (9)	0.0015 (8)	−0.0039 (10)
O2	0.0574 (9)	0.0434 (8)	0.0729 (9)	−0.0015 (7)	−0.0214 (8)	0.0012 (7)
O3	0.0584 (9)	0.0481 (8)	0.0746 (10)	0.0109 (7)	−0.0218 (8)	−0.0110 (7)
O4	0.0577 (9)	0.0459 (7)	0.0595 (8)	−0.0012 (7)	−0.0141 (7)	−0.0071 (6)
C1	0.0433 (11)	0.0560 (11)	0.0472 (10)	−0.0059 (10)	0.0009 (9)	−0.0014 (9)
C2	0.0372 (10)	0.0562 (12)	0.0617 (12)	−0.0049 (9)	−0.0018 (9)	−0.0084 (10)
C3	0.0535 (12)	0.0381 (9)	0.0544 (11)	0.0025 (9)	−0.0136 (10)	−0.0098 (8)
C4	0.0634 (14)	0.0506 (11)	0.0474 (10)	−0.0032 (11)	−0.0006 (10)	−0.0014 (9)
C5	0.0430 (11)	0.0542 (11)	0.0540 (11)	−0.0053 (10)	0.0062 (9)	−0.0046 (9)
C6	0.0381 (9)	0.0421 (10)	0.0481 (10)	−0.0023 (8)	0.0013 (8)	−0.0093 (8)
C7	0.0398 (11)	0.0466 (10)	0.0547 (11)	−0.0035 (9)	−0.0017 (9)	−0.0102 (8)
C8	0.0444 (11)	0.0434 (10)	0.0608 (12)	−0.0064 (9)	−0.0111 (9)	0.0010 (9)
C9	0.0505 (12)	0.0430 (10)	0.0398 (9)	0.0012 (9)	−0.0048 (8)	−0.0011 (8)
C10	0.0453 (10)	0.0437 (9)	0.0371 (8)	0.0042 (8)	−0.0024 (8)	0.0010 (7)
C11	0.0603 (14)	0.0510 (11)	0.0508 (11)	0.0078 (10)	−0.0030 (10)	−0.0057 (9)
C12	0.0679 (15)	0.0613 (14)	0.0671 (14)	0.0228 (13)	−0.0041 (12)	−0.0009 (11)
C13	0.0505 (13)	0.0780 (16)	0.0646 (13)	0.0163 (12)	−0.0071 (11)	0.0099 (12)
C14	0.0486 (12)	0.0654 (14)	0.0513 (11)	−0.0005 (11)	−0.0093 (10)	0.0052 (10)
C15	0.0475 (11)	0.0490 (10)	0.0362 (8)	0.0017 (9)	0.0003 (8)	0.0040 (7)
C16	0.0819 (18)	0.0597 (14)	0.0788 (16)	−0.0071 (13)	−0.0264 (15)	−0.0160 (11)

Br1—C3	1.900 (2)	C7—C8	1.505 (3)
O1—C7	1.203 (3)	C8—H8A	0.9700
O2—C9	1.351 (2)	C8—H8B	0.9700
O2—C8	1.423 (2)	C9—C10	1.485 (3)
O3—C9	1.197 (2)	C10—C11	1.394 (3)
O4—C15	1.356 (2)	C10—C15	1.408 (3)
O4—C16	1.430 (3)	C11—C12	1.377 (3)
C1—C2	1.378 (3)	C11—H11A	0.9300
C1—C6	1.395 (3)	C12—C13	1.375 (3)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.377 (3)	C13—C14	1.367 (3)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.376 (3)	C14—C15	1.386 (3)
C4—C5	1.371 (3)	C14—H14A	0.9300
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.389 (3)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.492 (3)
C9—O2—C8	115.94 (15)	H8A—C8—H8B	108.0
C15—O4—C16	118.42 (17)	O3—C9—O2	122.39 (19)
C2—C1—C6	120.95 (19)	O3—C9—C10	126.97 (18)
C2—C1—H1A	119.5	O2—C9—C10	110.63 (16)
C6—C1—H1A	119.5	C11—C10—C15	118.24 (19)
C3—C2—C1	118.55 (19)	C11—C10—C9	119.80 (18)
C3—C2—H2A	120.7	C15—C10—C9	121.96 (17)
C1—C2—H2A	120.7	C12—C11—C10	121.6 (2)
C4—C3—C2	121.9 (2)	C12—C11—H11A	119.2
C4—C3—Br1	119.56 (16)	C10—C11—H11A	119.2
C2—C3—Br1	118.56 (17)	C13—C12—C11	119.2 (2)
C5—C4—C3	119.1 (2)	C13—C12—H12A	120.4
C5—C4—H4A	120.5	C11—C12—H12A	120.4
C3—C4—H4A	120.5	C14—C13—C12	120.8 (2)
C4—C5—C6	120.9 (2)	C14—C13—H13A	119.6
C4—C5—H5A	119.5	C12—C13—H13A	119.6
C6—C5—H5A	119.5	C13—C14—C15	120.8 (2)
C5—C6—C1	118.64 (19)	C13—C14—H14A	119.6
C5—C6—C7	119.04 (18)	C15—C14—H14A	119.6
C1—C6—C7	122.30 (18)	O4—C15—C14	123.50 (19)
O1—C7—C6	121.99 (19)	O4—C15—C10	117.17 (17)
O1—C7—C8	120.4 (2)	C14—C15—C10	119.32 (19)
C6—C7—C8	117.61 (18)	O4—C16—H16A	109.5
O2—C8—C7	111.19 (18)	O4—C16—H16B	109.5
O2—C8—H8A	109.4	H16A—C16—H16B	109.5
C7—C8—H8A	109.4	O4—C16—H16C	109.5
O2—C8—H8B	109.4	H16A—C16—H16C	109.5
C7—C8—H8B	109.4	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.1 (3)	C8—O2—C9—C10	171.08 (17)
C1—C2—C3—C4	0.1 (3)	O3—C9—C10—C11	170.4 (2)
C1—C2—C3—Br1	178.86 (15)	O2—C9—C10—C11	−10.3 (3)
C2—C3—C4—C5	0.1 (3)	O3—C9—C10—C15	−10.5 (3)
Br1—C3—C4—C5	−178.69 (15)	O2—C9—C10—C15	168.90 (17)
C3—C4—C5—C6	−0.4 (3)	C15—C10—C11—C12	−0.2 (3)
C4—C5—C6—C1	0.5 (3)	C9—C10—C11—C12	179.0 (2)
C4—C5—C6—C7	179.23 (18)	C10—C11—C12—C13	−0.2 (3)
C2—C1—C6—C5	−0.4 (3)	C11—C12—C13—C14	0.5 (4)
C2—C1—C6—C7	−179.03 (19)	C12—C13—C14—C15	−0.6 (4)
C5—C6—C7—O1	4.6 (3)	C16—O4—C15—C14	0.5 (3)
C1—C6—C7—O1	−176.7 (2)	C16—O4—C15—C10	−178.7 (2)
C5—C6—C7—C8	−175.25 (18)	C13—C14—C15—O4	−179.0 (2)
C1—C6—C7—C8	3.4 (3)	C13—C14—C15—C10	0.2 (3)
C9—O2—C8—C7	−76.7 (2)	C11—C10—C15—O4	179.39 (17)
O1—C7—C8—O2	4.4 (3)	C9—C10—C15—O4	0.2 (3)
C6—C7—C8—O2	−175.70 (16)	C11—C10—C15—C14	0.1 (3)
C8—O2—C9—O3	−9.5 (3)	C9—C10—C15—C14	−179.03 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1i	0.93	2.45	3.360 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.93	2.45	3.360 (3)	165

Symmetry code: (i) .