4-Bromo-N-phenyl-benzamide.

The mol-ecule of the title benzamide derivative, C(13)H(10)BrNO, is twisted with the dihedral angle between the phenyl and 4-bromo-phenyl rings being 58.63 (9)°. The central N-C=O plane makes dihedral angles of 30.2 (2) and 29.2 (2)° with the phenyl and 4-bromo-phenyl rings, respectively. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into chains along [100]. C-H⋯π contacts combine with the N-H⋯O hydrogen bonds, to form a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Johnston & Taylor (2011 ▶); Li & Cui (2011 ▶); Saeed et al. (2008 ▶); Sripet et al. (2012 ▶). For background to and applications of benzamide derivatives, see: Boonleang & Tanthana (2010 ▶); Brown et al. (1991 ▶); Hu et al. (2008 ▶); Mobi­nikh­aledi et al. (2006 ▶); Olsson et al. (2002 ▶); World Health Organization (2003 ▶); Xu et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H10BrNO

M = 276.12

Triclinic,

a = 5.3552 (2) Å

b = 7.6334 (2) Å

c = 13.9956 (5) Å

α = 105.757 (3)°

β = 100.585 (3)°

γ = 90.086 (2)°

V = 540.45 (3) Å3

Z = 2

Mo Kα radiation

μ = 3.78 mm−1

T = 100 K

0.29 × 0.09 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.406, T max = 0.791

11303 measured reflections

3844 independent reflections

3193 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.076

S = 1.08

3844 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536812013487/sj5220sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013487/sj5220Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013487/sj5220Isup3.cml

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

C13H10BrNO	Z = 2
Mr = 276.12	F(000) = 276
Triclinic, P1	Dx = 1.697 Mg m−3
Hall symbol: -P 1	Melting point = 474–475 K
a = 5.3552 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6334 (2) Å	Cell parameters from 3844 reflections
c = 13.9956 (5) Å	θ = 2.8–32.5°
α = 105.757 (3)°	µ = 3.78 mm−1
β = 100.585 (3)°	T = 100 K
γ = 90.086 (2)°	Needle, colorless
V = 540.45 (3) Å3	0.29 × 0.09 × 0.07 mm

Bruker APEXII CCD area-detector diffractometer	3844 independent reflections
Radiation source: sealed tube	3193 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 32.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→8
Tmin = 0.406, Tmax = 0.791	k = −11→11
11303 measured reflections	l = −21→21

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0335P)2 + 0.2642P] where P = (Fo2 + 2Fc2)/3
3844 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.68 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	0.91443 (4)	0.72493 (3)	0.467544 (14)	0.01790 (7)
O1	1.1259 (3)	0.2407 (2)	0.00304 (11)	0.0175 (3)
N1	0.6913 (3)	0.2128 (2)	−0.03111 (12)	0.0119 (3)
H1N1	0.564 (5)	0.226 (4)	−0.003 (2)	0.020 (6)*
C1	0.9088 (4)	0.3807 (2)	0.13585 (13)	0.0112 (3)
C2	1.1145 (4)	0.3763 (2)	0.21293 (14)	0.0126 (3)
H2A	1.2533	0.3037	0.1972	0.015*
C3	1.1178 (4)	0.4768 (2)	0.31221 (14)	0.0134 (3)
H3A	1.2565	0.4728	0.3646	0.016*
C4	0.9141 (4)	0.5833 (2)	0.33308 (13)	0.0126 (3)
C5	0.7083 (4)	0.5916 (2)	0.25806 (14)	0.0130 (3)
H5A	0.5720	0.6666	0.2739	0.016*
C6	0.7057 (4)	0.4879 (2)	0.15909 (13)	0.0119 (3)
H6A	0.5649	0.4902	0.1072	0.014*
C7	0.9210 (4)	0.2720 (2)	0.03006 (14)	0.0128 (3)
C8	0.6473 (4)	0.1133 (2)	−0.13458 (13)	0.0112 (3)
C9	0.4262 (4)	0.0002 (2)	−0.17278 (14)	0.0124 (3)
H9A	0.3161	−0.0131	−0.1289	0.015*
C10	0.3667 (4)	−0.0932 (2)	−0.27495 (14)	0.0138 (3)
H10A	0.2160	−0.1701	−0.3005	0.017*
C11	0.5252 (4)	−0.0749 (2)	−0.33980 (13)	0.0138 (3)
H11A	0.4832	−0.1381	−0.4097	0.017*
C12	0.7467 (4)	0.0368 (3)	−0.30173 (14)	0.0141 (3)
H12A	0.8567	0.0487	−0.3459	0.017*
C13	0.8091 (4)	0.1317 (2)	−0.19935 (14)	0.0125 (3)
H13A	0.9603	0.2080	−0.1740	0.015*

	U11	U22	U33	U12	U13	U23
Br1	0.02581 (12)	0.01545 (9)	0.01116 (9)	0.00385 (7)	0.00550 (7)	0.00021 (6)
O1	0.0126 (7)	0.0236 (7)	0.0141 (6)	0.0029 (6)	0.0038 (5)	0.0005 (5)
N1	0.0110 (7)	0.0129 (7)	0.0117 (7)	0.0007 (6)	0.0045 (6)	0.0016 (5)
C1	0.0114 (8)	0.0100 (7)	0.0121 (7)	−0.0008 (6)	0.0039 (6)	0.0020 (6)
C2	0.0107 (8)	0.0118 (7)	0.0148 (8)	0.0018 (6)	0.0033 (6)	0.0021 (6)
C3	0.0147 (9)	0.0133 (8)	0.0119 (8)	0.0007 (7)	0.0021 (6)	0.0033 (6)
C4	0.0171 (9)	0.0097 (7)	0.0110 (7)	−0.0002 (7)	0.0057 (6)	0.0010 (6)
C5	0.0142 (9)	0.0108 (7)	0.0148 (8)	0.0022 (7)	0.0063 (7)	0.0027 (6)
C6	0.0125 (8)	0.0111 (7)	0.0116 (7)	0.0014 (6)	0.0026 (6)	0.0021 (6)
C7	0.0136 (9)	0.0127 (8)	0.0121 (8)	0.0021 (7)	0.0029 (6)	0.0034 (6)
C8	0.0135 (8)	0.0090 (7)	0.0115 (7)	0.0028 (6)	0.0031 (6)	0.0031 (6)
C9	0.0115 (8)	0.0109 (7)	0.0154 (8)	0.0017 (6)	0.0042 (6)	0.0037 (6)
C10	0.0116 (9)	0.0129 (8)	0.0159 (8)	0.0007 (7)	0.0019 (7)	0.0030 (6)
C11	0.0148 (9)	0.0131 (8)	0.0109 (7)	0.0027 (7)	0.0015 (6)	−0.0004 (6)
C12	0.0154 (9)	0.0148 (8)	0.0137 (8)	0.0037 (7)	0.0060 (7)	0.0045 (6)
C13	0.0124 (9)	0.0116 (7)	0.0140 (8)	0.0015 (7)	0.0040 (6)	0.0033 (6)

Br1—C4	1.8985 (18)	C5—H5A	0.9500
O1—C7	1.228 (2)	C6—H6A	0.9500
N1—C7	1.361 (2)	C8—C9	1.395 (3)
N1—C8	1.417 (2)	C8—C13	1.396 (3)
N1—H1N1	0.84 (3)	C9—C10	1.390 (3)
C1—C6	1.395 (3)	C9—H9A	0.9500
C1—C2	1.401 (2)	C10—C11	1.384 (3)
C1—C7	1.501 (2)	C10—H10A	0.9500
C2—C3	1.390 (3)	C11—C12	1.391 (3)
C2—H2A	0.9500	C11—H11A	0.9500
C3—C4	1.388 (3)	C12—C13	1.396 (3)
C3—H3A	0.9500	C12—H12A	0.9500
C4—C5	1.390 (3)	C13—H13A	0.9500
C5—C6	1.394 (2)
C7—N1—C8	126.73 (17)	O1—C7—N1	123.92 (17)
C7—N1—H1N1	116.5 (18)	O1—C7—C1	121.13 (17)
C8—N1—H1N1	116.4 (18)	N1—C7—C1	114.94 (16)
C6—C1—C2	119.54 (16)	C9—C8—C13	119.69 (16)
C6—C1—C7	122.67 (16)	C9—C8—N1	117.73 (17)
C2—C1—C7	117.76 (16)	C13—C8—N1	122.50 (17)
C3—C2—C1	120.71 (17)	C10—C9—C8	120.15 (18)
C3—C2—H2A	119.6	C10—C9—H9A	119.9
C1—C2—H2A	119.6	C8—C9—H9A	119.9
C4—C3—C2	118.53 (17)	C11—C10—C9	120.53 (18)
C4—C3—H3A	120.7	C11—C10—H10A	119.7
C2—C3—H3A	120.7	C9—C10—H10A	119.7
C3—C4—C5	122.06 (17)	C10—C11—C12	119.40 (17)
C3—C4—Br1	119.66 (14)	C10—C11—H11A	120.3
C5—C4—Br1	118.28 (14)	C12—C11—H11A	120.3
C4—C5—C6	118.79 (17)	C11—C12—C13	120.79 (18)
C4—C5—H5A	120.6	C11—C12—H12A	119.6
C6—C5—H5A	120.6	C13—C12—H12A	119.6
C5—C6—C1	120.35 (17)	C8—C13—C12	119.43 (17)
C5—C6—H6A	119.8	C8—C13—H13A	120.3
C1—C6—H6A	119.8	C12—C13—H13A	120.3
C6—C1—C2—C3	0.2 (3)	C2—C1—C7—O1	−28.1 (3)
C7—C1—C2—C3	178.64 (17)	C6—C1—C7—N1	−29.9 (3)
C1—C2—C3—C4	−0.7 (3)	C2—C1—C7—N1	151.72 (17)
C2—C3—C4—C5	0.1 (3)	C7—N1—C8—C9	153.01 (18)
C2—C3—C4—Br1	−179.15 (14)	C7—N1—C8—C13	−30.2 (3)
C3—C4—C5—C6	0.8 (3)	C13—C8—C9—C10	−0.3 (3)
Br1—C4—C5—C6	−179.88 (14)	N1—C8—C9—C10	176.59 (16)
C4—C5—C6—C1	−1.3 (3)	C8—C9—C10—C11	−0.1 (3)
C2—C1—C6—C5	0.7 (3)	C9—C10—C11—C12	0.5 (3)
C7—C1—C6—C5	−177.57 (17)	C10—C11—C12—C13	−0.6 (3)
C8—N1—C7—O1	−2.4 (3)	C9—C8—C13—C12	0.2 (3)
C8—N1—C7—C1	177.82 (16)	N1—C8—C13—C12	−176.50 (16)
C6—C1—C7—O1	150.22 (19)	C11—C12—C13—C8	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.84 (3)	2.37 (3)	3.150 (2)	156 (2)
C13—H13A···O1	0.95	2.42	2.923 (2)	113
C2—H2A···Cg2ii	0.95	2.77	3.4855 (19)	132
C5—H5A···Cg2iii	0.95	2.70	3.4258 (19)	134
C10—H10A···Cg1iv	0.95	2.90	3.5444 (19)	126
C13—H13A···Cg1v	0.95	2.84	3.4950 (19)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.84 (3)	2.37 (3)	3.150 (2)	156 (2)
C2—H2A⋯Cg2ii	0.95	2.77	3.4855 (19)	132
C5—H5A⋯Cg2iii	0.95	2.70	3.4258 (19)	134
C10—H10A⋯Cg1iv	0.95	2.90	3.5444 (19)	126
C13—H13A⋯Cg1v	0.95	2.84	3.4950 (19)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .