4-Methyl-phenyl 4-bromo-benzoate.

In the title compound, C(14)H(11)BrO(2), an ester formed from the reaction of 4-methyl-phenol with 4-bromo-benzoyl-chloride, the dihedral angle between the benzene rings is 54.43 (7)°, indicating a twist in the mol-ecule. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into supra-molecular layers in the bc plane, and these are connected along the a axis by Br⋯Br contacts [3.6328 (5) Å].

Related literature

For industrial applications of ester systems, see: Gowda et al. (2007a ▶); Brüning et al. (2009 ▶). For related structures, see: Gowda et al. (2007b ▶, 2008 ▶). For hydrogen bonding, see: Nardelli (1995 ▶). For halogen inter­actions, see: Ritter (2009 ▶).

Experimental

Crystal data

C14H11BrO2

M = 291.13

Monoclinic,

a = 15.0219 (9) Å

b = 11.3585 (8) Å

c = 7.5077 (4) Å

β = 99.730 (4)°

V = 1262.58 (14) Å3

Z = 4

Mo Kα radiation

μ = 3.24 mm−1

T = 293 K

0.47 × 0.18 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.472, T max = 0.698

9090 measured reflections

2829 independent reflections

1811 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 1.01

2829 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.36 e Å−3

Data collection: COLLECT (Nonius, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040426/tk2795sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040426/tk2795Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040426/tk2795Isup3.cml

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

C14H11BrO2	F(000) = 584
Mr = 291.13	Dx = 1.532 Mg m−3
Monoclinic, P21/c	Melting point: 385(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.0219 (9) Å	Cell parameters from 9005 reflections
b = 11.3585 (8) Å	θ = 2.9–27.5°
c = 7.5077 (4) Å	µ = 3.24 mm−1
β = 99.730 (4)°	T = 293 K
V = 1262.58 (14) Å3	Prism, colourless
Z = 4	0.47 × 0.18 × 0.10 mm

Bruker–Nonius KappaCCD diffractometer	2829 independent reflections
Radiation source: fine-focus sealed tube	1811 reflections with I > 2σ(I)
horizonally mounted graphite crystal	Rint = 0.052
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.7°
CCD scans	h = −19→19
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→10
Tmin = 0.472, Tmax = 0.698	l = −9→9
9090 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.3548P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2829 reflections	Δρmax = 0.31 e Å−3
156 parameters	Δρmin = −0.36 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (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	0.61020 (2)	0.93326 (4)	0.00395 (6)	0.0970 (2)
C14	1.4444 (2)	0.8443 (4)	0.4571 (6)	0.1050 (13)
H14A	1.4685	0.8902	0.5615	0.158*
H14B	1.4718	0.8687	0.3564	0.158*
H14C	1.4572	0.7625	0.4817	0.158*
O2	1.06435 (14)	0.91018 (16)	0.2775 (3)	0.0640 (5)
O1	1.02822 (15)	0.7422 (2)	0.4071 (3)	0.0864 (7)
C5	0.8438 (2)	0.7772 (2)	0.2633 (4)	0.0615 (7)
H5	0.8594	0.7079	0.3270	0.074*
C1	0.7324 (2)	0.9019 (3)	0.0998 (4)	0.0631 (7)
C3	0.8867 (2)	0.9613 (2)	0.1444 (4)	0.0590 (6)
H3	0.9309	1.0156	0.1275	0.071*
C2	0.7978 (2)	0.9834 (3)	0.0749 (4)	0.0619 (7)
H2	0.7815	1.0526	0.0116	0.074*
C8	1.15716 (19)	0.8889 (2)	0.3280 (3)	0.0558 (6)
C7	1.0054 (2)	0.8281 (3)	0.3177 (4)	0.0617 (7)
C4	0.91105 (18)	0.8576 (2)	0.2403 (3)	0.0545 (6)
C6	0.7555 (2)	0.7987 (3)	0.1938 (4)	0.0663 (7)
H6	0.7111	0.7444	0.2095	0.080*
C11	1.3432 (2)	0.8623 (3)	0.4124 (4)	0.0723 (8)
C13	1.1971 (2)	0.7893 (2)	0.2718 (4)	0.0641 (7)
H13	1.1624	0.7313	0.2056	0.077*
C9	1.2087 (2)	0.9753 (3)	0.4252 (4)	0.0636 (7)
H9	1.1814	1.0422	0.4630	0.076*
C12	1.2891 (2)	0.7777 (3)	0.3156 (4)	0.0710 (8)
H12	1.3161	0.7103	0.2789	0.085*
C10	1.3008 (2)	0.9615 (3)	0.4656 (4)	0.0720 (8)
H10	1.3355	1.0202	0.5302	0.086*

	U11	U22	U33	U12	U13	U23
Br1	0.0691 (3)	0.1091 (4)	0.1086 (4)	0.00332 (19)	0.00328 (19)	0.0103 (2)
C14	0.067 (2)	0.107 (3)	0.140 (3)	0.002 (2)	0.014 (2)	0.004 (3)
O2	0.0677 (12)	0.0511 (11)	0.0726 (11)	0.0013 (9)	0.0099 (9)	0.0076 (9)
O1	0.0789 (14)	0.0797 (15)	0.0998 (15)	0.0048 (12)	0.0129 (11)	0.0395 (13)
C5	0.0802 (19)	0.0442 (14)	0.0603 (14)	−0.0036 (13)	0.0130 (13)	0.0073 (11)
C1	0.0668 (16)	0.0635 (17)	0.0598 (15)	0.0025 (14)	0.0127 (12)	−0.0013 (13)
C3	0.0727 (17)	0.0450 (14)	0.0630 (14)	−0.0011 (12)	0.0221 (13)	0.0035 (11)
C2	0.0724 (17)	0.0500 (15)	0.0656 (15)	0.0088 (14)	0.0187 (13)	0.0065 (13)
C8	0.0665 (16)	0.0492 (14)	0.0530 (13)	0.0001 (12)	0.0137 (11)	0.0047 (11)
C7	0.0760 (18)	0.0527 (15)	0.0577 (14)	−0.0008 (14)	0.0145 (12)	0.0066 (13)
C4	0.0695 (16)	0.0446 (14)	0.0507 (13)	0.0012 (12)	0.0141 (11)	0.0017 (10)
C6	0.0751 (18)	0.0569 (17)	0.0677 (15)	−0.0106 (14)	0.0144 (13)	0.0014 (13)
C11	0.0743 (18)	0.066 (2)	0.0790 (18)	0.0034 (15)	0.0196 (15)	0.0049 (15)
C13	0.0816 (19)	0.0510 (15)	0.0596 (14)	0.0004 (14)	0.0118 (13)	−0.0032 (12)
C9	0.0733 (18)	0.0506 (15)	0.0700 (16)	−0.0020 (14)	0.0212 (13)	−0.0066 (13)
C12	0.086 (2)	0.0580 (17)	0.0729 (17)	0.0097 (16)	0.0240 (15)	−0.0012 (14)
C10	0.078 (2)	0.0616 (18)	0.0766 (18)	−0.0107 (15)	0.0145 (15)	−0.0076 (14)

Br1—C1	1.889 (3)	C3—H3	0.9300
C14—C11	1.515 (5)	C2—H2	0.9300
C14—H14A	0.9600	C8—C9	1.380 (4)
C14—H14B	0.9600	C8—C13	1.380 (4)
C14—H14C	0.9600	C7—C4	1.477 (4)
O2—C7	1.355 (3)	C6—H6	0.9300
O2—C8	1.402 (3)	C11—C10	1.386 (5)
O1—C7	1.200 (3)	C11—C12	1.383 (5)
C5—C6	1.363 (4)	C13—C12	1.372 (4)
C5—C4	1.394 (4)	C13—H13	0.9300
C5—H5	0.9300	C9—C10	1.375 (4)
C1—C6	1.382 (4)	C9—H9	0.9300
C1—C2	1.384 (4)	C12—H12	0.9300
C3—C2	1.373 (4)	C10—H10	0.9300
C3—C4	1.397 (4)
C11—C14—H14A	109.5	O1—C7—C4	124.7 (3)
C11—C14—H14B	109.5	O2—C7—C4	112.1 (2)
H14A—C14—H14B	109.5	C5—C4—C3	119.0 (3)
C11—C14—H14C	109.5	C5—C4—C7	118.0 (2)
H14A—C14—H14C	109.5	C3—C4—C7	123.0 (2)
H14B—C14—H14C	109.5	C5—C6—C1	119.4 (3)
C7—O2—C8	118.6 (2)	C5—C6—H6	120.3
C6—C5—C4	120.9 (3)	C1—C6—H6	120.3
C6—C5—H5	119.6	C10—C11—C12	117.3 (3)
C4—C5—H5	119.6	C10—C11—C14	122.6 (3)
C6—C1—C2	120.9 (3)	C12—C11—C14	120.1 (3)
C6—C1—Br1	119.9 (2)	C12—C13—C8	118.5 (3)
C2—C1—Br1	119.2 (2)	C12—C13—H13	120.7
C2—C3—C4	120.2 (3)	C8—C13—H13	120.7
C2—C3—H3	119.9	C10—C9—C8	119.3 (3)
C4—C3—H3	119.9	C10—C9—H9	120.3
C3—C2—C1	119.6 (3)	C8—C9—H9	120.3
C3—C2—H2	120.2	C13—C12—C11	122.6 (3)
C1—C2—H2	120.2	C13—C12—H12	118.7
C9—C8—C13	120.7 (3)	C11—C12—H12	118.7
C9—C8—O2	117.6 (2)	C9—C10—C11	121.6 (3)
C13—C8—O2	121.5 (3)	C9—C10—H10	119.2
O1—C7—O2	123.3 (3)	C11—C10—H10	119.2
C4—C3—C2—C1	−0.3 (4)	O2—C7—C4—C3	−2.8 (4)
C6—C1—C2—C3	0.1 (4)	C4—C5—C6—C1	−0.2 (4)
Br1—C1—C2—C3	179.9 (2)	C2—C1—C6—C5	0.2 (4)
C7—O2—C8—C9	−128.0 (3)	Br1—C1—C6—C5	−179.6 (2)
C7—O2—C8—C13	56.6 (3)	C9—C8—C13—C12	0.4 (4)
C8—O2—C7—O1	6.1 (4)	O2—C8—C13—C12	175.6 (2)
C8—O2—C7—C4	−174.3 (2)	C13—C8—C9—C10	0.2 (4)
C6—C5—C4—C3	0.0 (4)	O2—C8—C9—C10	−175.2 (2)
C6—C5—C4—C7	−179.4 (2)	C8—C13—C12—C11	−0.6 (4)
C2—C3—C4—C5	0.3 (4)	C10—C11—C12—C13	0.2 (5)
C2—C3—C4—C7	179.7 (2)	C14—C11—C12—C13	179.8 (3)
O1—C7—C4—C5	−3.8 (4)	C8—C9—C10—C11	−0.6 (5)
O2—C7—C4—C5	176.6 (2)	C12—C11—C10—C9	0.4 (5)
O1—C7—C4—C3	176.7 (3)	C14—C11—C10—C9	−179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.67	3.483 (4)	147.
C13—H13···O1ii	0.93	2.77	3.422 (4)	128.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.67	3.483 (4)	147
C13—H13⋯O1ii	0.93	2.77	3.422 (4)	128

Symmetry codes: (i) ; (ii) .