4-Bromo-phenyl benzoate.

The structure of the title compound (4BPBA), C(13)H(9)BrO(2), is similar to that of phenyl benzoate (PBA), 4-methyl-phenyl benzoate (4MePBA) and 4-methoxy-phenyl benzoate, with somewhat different bond parameters. The dihedral angle between the phenyl and benzoyl rings in 4BPBA is 58.43 (17)°, compared with values of 55.7° in PBA and 60.17 (7)° in 4MPBA. The mol-ecules in the title compound are packed into infinite chains in the a-axis direction.

Related literature

For related literature, see: Adams & Morsi (1976 ▶); Gowda, Foro, Babitha & Fuess (2007 ▶); Gowda, Foro, Nayak & Fuess (2007 ▶); Nayak & Gowda (2008 ▶).

Experimental

Crystal data

C13H9BrO2

M = 277.11

Orthorhombic,

a = 7.748 (1) Å

b = 5.5946 (7) Å

c = 26.814 (5) Å

V = 1162.3 (3) Å3

Z = 4

Cu Kα radiation

μ = 4.67 mm−1

T = 299 (2) K

0.38 × 0.30 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.241, T max = 0.685

1986 measured reflections

1442 independent reflections

1252 reflections with I > 2σ(I)

R int = 0.039

3 standard reflections frequency: 120 min intensity decay: 2.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.189

S = 1.15

1442 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.04 e Å−3

Δρmin = −1.32 e Å−3

Absolute structure: Flack (1983 ▶), with 375 Friedel pairs

Flack parameter: −0.04 (6)

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC Software; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008167/om2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008167/om2221Isup2.hkl

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

C13H9BrO2	F000 = 552
Mr = 277.11	Dx = 1.584 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation λ = 1.54180 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 7.748 (1) Å	θ = 9.9–23.4º
b = 5.5946 (7) Å	µ = 4.67 mm−1
c = 26.814 (5) Å	T = 299 (2) K
V = 1162.3 (3) Å3	Plate, colourless
Z = 4	0.38 × 0.30 × 0.08 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.039
Radiation source: fine-focus sealed tube	θmax = 66.9º
Monochromator: graphite	θmin = 3.3º
T = 299(2) K	h = −1→9
ω/2θ scans	k = −1→6
Absorption correction: ψ scan(North et al., 1968)	l = −8→32
Tmin = 0.242, Tmax = 0.685	3 standard reflections
1986 measured reflections	every 120 min
1442 independent reflections	intensity decay: 2.0%
1252 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059	w = 1/[σ2(Fo2) + (0.1268P)2 + 0.565P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.189	(Δ/σ)max = 0.001
S = 1.15	Δρmax = 1.04 e Å−3
1442 reflections	Δρmin = −1.32 e Å−3
145 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), with 375 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (6)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
Br1	0.29159 (16)	0.2659 (2)	−0.12742 (8)	0.0950 (5)
O1	0.4692 (6)	0.1882 (9)	0.0901 (2)	0.0581 (13)
O2	0.3231 (11)	0.5195 (14)	0.1104 (3)	0.107 (3)
C1	0.4260 (8)	0.2190 (10)	0.0403 (3)	0.0463 (14)
C2	0.4854 (8)	0.4121 (12)	0.0127 (3)	0.0544 (16)
H2	0.5500	0.5321	0.0278	0.065*
C3	0.4478 (8)	0.4229 (12)	−0.0367 (3)	0.0560 (17)
H3	0.4888	0.5492	−0.0559	0.067*
C4	0.3474 (11)	0.2440 (12)	−0.0586 (3)	0.0559 (17)
C5	0.2920 (9)	0.0437 (12)	−0.0313 (3)	0.0589 (18)
H5	0.2301	−0.0794	−0.0462	0.071*
C6	0.3332 (9)	0.0389 (13)	0.0176 (3)	0.0583 (17)
H6	0.2977	−0.0908	0.0368	0.070*
C7	0.4106 (9)	0.3510 (14)	0.1226 (3)	0.0577 (17)
C8	0.4601 (9)	0.2976 (12)	0.1748 (3)	0.0521 (15)
C9	0.5527 (8)	0.0900 (13)	0.1879 (3)	0.0585 (17)
H9	0.5846	−0.0209	0.1638	0.070*
C10	0.5943 (10)	0.0558 (13)	0.2368 (4)	0.0644 (19)
H10	0.6544	−0.0820	0.2454	0.077*
C11	0.5530 (10)	0.2107 (14)	0.2731 (4)	0.0627 (19)
H11	0.5834	0.1803	0.3060	0.075*
C12	0.4636 (9)	0.4180 (14)	0.2604 (3)	0.0602 (17)
H12	0.4353	0.5284	0.2851	0.072*
C13	0.4164 (9)	0.4607 (13)	0.2112 (3)	0.0585 (16)
H13	0.3558	0.5985	0.2029	0.070*

	U11	U22	U33	U12	U13	U23
Br1	0.1056 (8)	0.1322 (9)	0.0472 (6)	0.0167 (6)	−0.0058 (7)	−0.0056 (7)
O1	0.053 (2)	0.064 (3)	0.058 (3)	0.008 (2)	−0.003 (2)	−0.011 (3)
O2	0.145 (6)	0.117 (5)	0.059 (4)	0.089 (5)	0.005 (4)	0.001 (4)
C1	0.044 (3)	0.047 (3)	0.049 (4)	0.003 (2)	−0.001 (3)	−0.003 (3)
C2	0.046 (3)	0.052 (3)	0.066 (5)	−0.007 (3)	0.004 (3)	−0.009 (3)
C3	0.055 (3)	0.052 (3)	0.061 (5)	0.007 (3)	0.011 (3)	0.005 (3)
C4	0.058 (4)	0.067 (4)	0.042 (4)	0.006 (3)	0.005 (4)	−0.006 (3)
C5	0.062 (4)	0.049 (3)	0.066 (5)	−0.004 (3)	−0.005 (4)	−0.006 (3)
C6	0.054 (3)	0.058 (4)	0.063 (5)	−0.012 (3)	0.002 (4)	0.010 (4)
C7	0.050 (3)	0.068 (4)	0.055 (4)	0.019 (3)	0.004 (3)	0.002 (4)
C8	0.051 (3)	0.055 (3)	0.050 (4)	−0.005 (3)	0.006 (3)	−0.001 (3)
C9	0.053 (3)	0.062 (3)	0.061 (4)	0.017 (3)	−0.004 (3)	−0.010 (4)
C10	0.057 (3)	0.062 (4)	0.074 (5)	0.007 (3)	−0.008 (4)	0.015 (4)
C11	0.056 (3)	0.082 (5)	0.050 (5)	−0.001 (3)	−0.002 (3)	0.003 (4)
C12	0.064 (4)	0.065 (4)	0.052 (4)	−0.007 (3)	0.005 (4)	−0.002 (4)
C13	0.056 (3)	0.059 (4)	0.060 (4)	0.010 (3)	−0.003 (3)	0.001 (3)

Br1—C4	1.899 (9)	C6—H6	0.9300
O1—C7	1.340 (10)	C7—C8	1.481 (12)
O1—C1	1.388 (10)	C8—C13	1.379 (11)
O2—C7	1.206 (9)	C8—C9	1.410 (10)
C1—C6	1.379 (10)	C9—C10	1.364 (12)
C1—C2	1.388 (10)	C9—H9	0.9300
C2—C3	1.356 (12)	C10—C11	1.342 (12)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.398 (11)	C11—C12	1.392 (11)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.406 (11)	C12—C13	1.390 (12)
C5—C6	1.351 (12)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C7—O1—C1	117.4 (5)	O2—C7—C8	124.1 (7)
C6—C1—C2	120.4 (8)	O1—C7—C8	112.9 (6)
C6—C1—O1	117.3 (6)	C13—C8—C9	119.5 (8)
C2—C1—O1	122.0 (6)	C13—C8—C7	118.2 (6)
C3—C2—C1	118.9 (6)	C9—C8—C7	122.2 (7)
C3—C2—H2	120.5	C10—C9—C8	118.4 (7)
C1—C2—H2	120.5	C10—C9—H9	120.8
C2—C3—C4	119.9 (7)	C8—C9—H9	120.8
C2—C3—H3	120.1	C11—C10—C9	123.4 (7)
C4—C3—H3	120.1	C11—C10—H10	118.3
C3—C4—C5	121.4 (8)	C9—C10—H10	118.3
C3—C4—Br1	119.3 (6)	C10—C11—C12	118.7 (8)
C5—C4—Br1	119.2 (6)	C10—C11—H11	120.7
C6—C5—C4	116.7 (7)	C12—C11—H11	120.7
C6—C5—H5	121.6	C13—C12—C11	120.4 (8)
C4—C5—H5	121.6	C13—C12—H12	119.8
C5—C6—C1	122.4 (7)	C11—C12—H12	119.8
C5—C6—H6	118.8	C8—C13—C12	119.6 (7)
C1—C6—H6	118.8	C8—C13—H13	120.2
O2—C7—O1	123.0 (8)	C12—C13—H13	120.2
C7—O1—C1—C6	−120.1 (7)	C1—O1—C7—C8	178.5 (6)
C7—O1—C1—C2	65.4 (9)	O2—C7—C8—C13	−5.8 (12)
C6—C1—C2—C3	1.3 (10)	O1—C7—C8—C13	175.9 (6)
O1—C1—C2—C3	175.6 (6)	O2—C7—C8—C9	175.6 (9)
C1—C2—C3—C4	1.4 (10)	O1—C7—C8—C9	−2.7 (10)
C2—C3—C4—C5	−3.8 (10)	C13—C8—C9—C10	0.9 (10)
C2—C3—C4—Br1	178.5 (5)	C7—C8—C9—C10	179.5 (7)
C3—C4—C5—C6	3.2 (10)	C8—C9—C10—C11	−0.6 (12)
Br1—C4—C5—C6	−179.1 (6)	C9—C10—C11—C12	−0.3 (12)
C4—C5—C6—C1	−0.5 (11)	C10—C11—C12—C13	0.9 (11)
C2—C1—C6—C5	−1.8 (11)	C9—C8—C13—C12	−0.3 (11)
O1—C1—C6—C5	−176.4 (7)	C7—C8—C13—C12	−178.9 (7)
C1—O1—C7—O2	0.2 (12)	C11—C12—C13—C8	−0.6 (11)