N-(4-Bromo-phen-yl)-4-nitro-benzamide.

In the title compound, C(13)H(9)BrN(2)O(3), the dihedral angle between the mean planes of the two benzene rings is 3.6 (7)°. The amide group is twisted by 28.1 (6) and 31.8 (3)° from the mean planes of the 4-bromo-phenyl and 4-nitro-benzene rings, respectively. The crystal packing features weak inter-molecular N-H⋯O and C-H⋯O hydrogen bonds resulting in a three-dimensional network.

Related literature

For the anti­microbial activity of amides, see: Priya et al. (2005 ▶). For the use of amides in supra­molecular chemical anion sensor technology, see: Jagessar & Rampersaud (2007 ▶). For a related structure, see: Gowda et al. (2008 ▶);

Experimental

Crystal data

C13H9BrN2O3

M = 321.13

Monoclinic,

a = 4.57903 (6) Å

b = 12.92579 (15) Å

c = 20.5614 (3) Å

β = 96.0333 (11)°

V = 1210.24 (3) Å3

Z = 4

Cu Kα radiation

μ = 4.70 mm−1

T = 123 K

0.48 × 0.12 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.485, T max = 1.000

8049 measured reflections

2434 independent reflections

2329 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.075

S = 1.06

2434 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000122/pv2370sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000122/pv2370Isup2.hkl

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

C13H9BrN2O3	F(000) = 640
Mr = 321.13	Dx = 1.762 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 7736 reflections
a = 4.57903 (6) Å	θ = 5.5–73.9°
b = 12.92579 (15) Å	µ = 4.70 mm−1
c = 20.5614 (3) Å	T = 123 K
β = 96.0333 (11)°	Needle, colorless
V = 1210.24 (3) Å3	0.48 × 0.12 × 0.07 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2434 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2329 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.5081 pixels mm-1	θmax = 74.0°, θmin = 5.5°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −15→15
Tmin = 0.485, Tmax = 1.000	l = −20→25
8049 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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.6292P] where P = (Fo2 + 2Fc2)/3
2434 reflections	(Δ/σ)max = 0.002
172 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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
Br	0.32019 (4)	0.406567 (14)	0.541374 (10)	0.02940 (10)
O1	0.3492 (3)	−0.11877 (10)	0.59423 (6)	0.0247 (3)
O2	−0.5374 (3)	−0.46316 (11)	0.76725 (7)	0.0345 (3)
O3	−0.2924 (4)	−0.55958 (11)	0.70717 (8)	0.0377 (4)
N1	−0.0486 (3)	−0.02526 (11)	0.61758 (7)	0.0201 (3)
H1A	−0.2223	−0.0300	0.6320	0.024*
N2	−0.3666 (3)	−0.47512 (12)	0.72579 (7)	0.0231 (3)
C1	0.0405 (3)	0.07385 (13)	0.59764 (8)	0.0182 (3)
C2	0.2236 (4)	0.08785 (13)	0.54822 (9)	0.0201 (3)
H2A	0.2927	0.0295	0.5262	0.024*
C3	0.3048 (4)	0.18693 (15)	0.53110 (8)	0.0219 (3)
H3A	0.4303	0.1968	0.4976	0.026*
C4	0.2009 (4)	0.27132 (13)	0.56336 (8)	0.0198 (3)
C5	0.0130 (4)	0.25951 (14)	0.61141 (9)	0.0239 (4)
H5A	−0.0597	0.3182	0.6324	0.029*
C6	−0.0673 (4)	0.16009 (14)	0.62825 (9)	0.0230 (3)
H6A	−0.1968	0.1508	0.6610	0.028*
C7	0.1117 (3)	−0.11336 (13)	0.61622 (8)	0.0178 (3)
C8	−0.0198 (3)	−0.20704 (13)	0.64528 (8)	0.0184 (3)
C9	−0.1905 (4)	−0.19869 (13)	0.69742 (8)	0.0200 (3)
H9A	−0.2286	−0.1325	0.7148	0.024*
C10	−0.3050 (4)	−0.28705 (14)	0.72402 (8)	0.0213 (3)
H10A	−0.4215	−0.2822	0.7595	0.026*
C11	−0.2449 (4)	−0.38172 (14)	0.69751 (8)	0.0194 (3)
C12	−0.0747 (4)	−0.39293 (14)	0.64586 (9)	0.0231 (4)
H12A	−0.0373	−0.4593	0.6287	0.028*
C13	0.0391 (4)	−0.30400 (14)	0.62015 (8)	0.0222 (3)
H13A	0.1581	−0.3094	0.5851	0.027*

	U11	U22	U33	U12	U13	U23
Br	0.03917 (15)	0.01765 (14)	0.03289 (15)	−0.00443 (7)	0.01082 (9)	0.00390 (6)
O1	0.0192 (6)	0.0241 (6)	0.0322 (7)	0.0024 (5)	0.0095 (5)	0.0045 (5)
O2	0.0452 (8)	0.0239 (7)	0.0383 (8)	−0.0015 (6)	0.0233 (6)	0.0050 (6)
O3	0.0576 (10)	0.0158 (7)	0.0431 (8)	0.0013 (6)	0.0210 (7)	0.0009 (6)
N1	0.0158 (6)	0.0194 (7)	0.0264 (7)	−0.0010 (5)	0.0077 (5)	0.0028 (6)
N2	0.0279 (7)	0.0197 (8)	0.0222 (7)	0.0006 (6)	0.0048 (6)	0.0032 (6)
C1	0.0165 (7)	0.0188 (8)	0.0194 (8)	−0.0016 (6)	0.0019 (6)	0.0027 (6)
C2	0.0211 (8)	0.0190 (9)	0.0212 (8)	−0.0009 (6)	0.0065 (6)	−0.0020 (6)
C3	0.0235 (8)	0.0211 (9)	0.0223 (8)	−0.0021 (6)	0.0077 (6)	0.0008 (7)
C4	0.0219 (8)	0.0152 (8)	0.0224 (8)	−0.0030 (6)	0.0025 (6)	0.0049 (6)
C5	0.0289 (8)	0.0199 (9)	0.0241 (8)	0.0023 (7)	0.0079 (7)	0.0008 (7)
C6	0.0245 (8)	0.0231 (9)	0.0233 (8)	0.0029 (7)	0.0110 (6)	0.0028 (7)
C7	0.0153 (7)	0.0199 (8)	0.0184 (8)	−0.0010 (6)	0.0026 (6)	0.0008 (6)
C8	0.0153 (7)	0.0202 (8)	0.0194 (7)	0.0006 (6)	0.0012 (6)	0.0028 (6)
C9	0.0232 (8)	0.0157 (8)	0.0217 (8)	0.0019 (6)	0.0050 (6)	−0.0005 (6)
C10	0.0236 (8)	0.0209 (9)	0.0203 (8)	0.0019 (6)	0.0065 (6)	0.0025 (6)
C11	0.0216 (8)	0.0171 (8)	0.0196 (8)	0.0000 (6)	0.0022 (6)	0.0035 (6)
C12	0.0284 (9)	0.0174 (8)	0.0244 (8)	0.0025 (7)	0.0075 (7)	−0.0014 (6)
C13	0.0240 (8)	0.0220 (9)	0.0220 (8)	0.0011 (6)	0.0091 (6)	0.0006 (7)

Br—C4	1.9002 (17)	C5—C6	1.390 (3)
O1—C7	1.223 (2)	C5—H5A	0.9500
O2—N2	1.226 (2)	C6—H6A	0.9500
O3—N2	1.217 (2)	C7—C8	1.504 (2)
N1—C7	1.357 (2)	C8—C13	1.393 (2)
N1—C1	1.418 (2)	C8—C9	1.396 (2)
N1—H1A	0.8800	C9—C10	1.392 (2)
N2—C11	1.475 (2)	C9—H9A	0.9500
C1—C2	1.395 (2)	C10—C11	1.379 (3)
C1—C6	1.396 (3)	C10—H10A	0.9500
C2—C3	1.389 (2)	C11—C12	1.389 (3)
C2—H2A	0.9500	C12—C13	1.389 (3)
C3—C4	1.387 (3)	C12—H12A	0.9500
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.385 (2)
C7—N1—C1	125.41 (14)	C1—C6—H6A	119.6
C7—N1—H1A	117.3	O1—C7—N1	124.04 (16)
C1—N1—H1A	117.3	O1—C7—C8	120.64 (16)
O3—N2—O2	123.49 (16)	N1—C7—C8	115.31 (14)
O3—N2—C11	118.72 (15)	C13—C8—C9	120.04 (16)
O2—N2—C11	117.79 (15)	C13—C8—C7	118.42 (15)
C2—C1—C6	119.53 (16)	C9—C8—C7	121.52 (15)
C2—C1—N1	122.74 (16)	C10—C9—C8	120.17 (16)
C6—C1—N1	117.71 (15)	C10—C9—H9A	119.9
C3—C2—C1	120.10 (16)	C8—C9—H9A	119.9
C3—C2—H2A	120.0	C11—C10—C9	118.27 (16)
C1—C2—H2A	120.0	C11—C10—H10A	120.9
C4—C3—C2	119.30 (15)	C9—C10—H10A	120.9
C4—C3—H3A	120.3	C10—C11—C12	123.09 (16)
C2—C3—H3A	120.3	C10—C11—N2	118.11 (15)
C5—C4—C3	121.64 (16)	C12—C11—N2	118.80 (16)
C5—C4—Br	119.13 (13)	C13—C12—C11	117.87 (17)
C3—C4—Br	119.23 (13)	C13—C12—H12A	121.1
C4—C5—C6	118.67 (16)	C11—C12—H12A	121.1
C4—C5—H5A	120.7	C12—C13—C8	120.55 (16)
C6—C5—H5A	120.7	C12—C13—H13A	119.7
C5—C6—C1	120.71 (16)	C8—C13—H13A	119.7
C5—C6—H6A	119.6
C7—N1—C1—C2	31.0 (3)	O1—C7—C8—C9	146.78 (17)
C7—N1—C1—C6	−150.50 (17)	N1—C7—C8—C9	−32.2 (2)
C6—C1—C2—C3	2.0 (3)	C13—C8—C9—C10	−0.7 (2)
N1—C1—C2—C3	−179.60 (15)	C7—C8—C9—C10	−178.88 (15)
C1—C2—C3—C4	−0.3 (3)	C8—C9—C10—C11	0.0 (2)
C2—C3—C4—C5	−1.3 (3)	C9—C10—C11—C12	0.3 (3)
C2—C3—C4—Br	178.45 (13)	C9—C10—C11—N2	−179.98 (15)
C3—C4—C5—C6	1.3 (3)	O3—N2—C11—C10	−173.01 (17)
Br—C4—C5—C6	−178.45 (13)	O2—N2—C11—C10	6.7 (2)
C4—C5—C6—C1	0.3 (3)	O3—N2—C11—C12	6.7 (2)
C2—C1—C6—C5	−2.0 (3)	O2—N2—C11—C12	−173.58 (16)
N1—C1—C6—C5	179.52 (16)	C10—C11—C12—C13	0.0 (3)
C1—N1—C7—O1	−3.9 (3)	N2—C11—C12—C13	−179.68 (15)
C1—N1—C7—C8	175.02 (14)	C11—C12—C13—C8	−0.7 (3)
O1—C7—C8—C13	−31.4 (2)	C9—C8—C13—C12	1.0 (2)
N1—C7—C8—C13	149.60 (16)	C7—C8—C13—C12	179.28 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.88	2.33	3.0026 (18)	133
N1—H1A···O2ii	0.88	2.59	3.284 (2)	136
C3—H3A···O1iii	0.95	2.45	3.284 (2)	146
C5—H5A···O3iv	0.95	2.52	3.447 (2)	166
C6—H6A···O2ii	0.95	2.49	3.354 (2)	151
C9—H9A···O2ii	0.95	2.48	3.397 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.88	2.33	3.0026 (18)	133
N1—H1A⋯O2ii	0.88	2.59	3.284 (2)	136
C3—H3A⋯O1iii	0.95	2.45	3.284 (2)	146
C5—H5A⋯O3iv	0.95	2.52	3.447 (2)	166
C6—H6A⋯O2ii	0.95	2.49	3.354 (2)	151
C9—H9A⋯O2ii	0.95	2.48	3.397 (2)	162

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