N-(4-Bromo­phen­yl)-4-nitro­benzamide

Saeed, S.; Jasinski, J.P.; Butcher, R.J.

doi:10.1107/S1600536811000122

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o279

doi:10.1107/S1600536811000122

Open

access

N-(4-Bromophenyl)-4-nitrobenzamide

Sohail Saeed,^a ^* Jerry P. Jasinski ^b and Ray J. Butcher ^c

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: sohail262001@yahoo.com

(Received 12 December 2010; accepted 4 January 2011; online 8 January 2011)

In the title compound, C₁₃H₉BrN₂O₃, 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-bromophenyl and 4-nitrobenzene rings, respectively. The crystal packing features weak intermolecular 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_r = 321.13
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) 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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.075
S = 1.06
2434 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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⋯O3^iv	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) x-1, y, z; (ii) $[-x-1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y, -z+1; (iv) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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 ).

Supporting information

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

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

checkCIF report

Comment top

Amides are known to play a pivitol role in molecular recognition, being important components in supramolecular chemical anion sensors technology (Jagessar & Rampersaud, 2007). Moreover, amides have also been reported as antimicrobial agents (Priya et al., 2005). The structure of the title compound has been determined to explore the effect of substituents on the structure of benzanilides.

In the title compound (Fig. 1), 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-bromophenyl and 4-nitrobenzene rings. The bond distances and angles in the title compound agree well with the corresponding bond distances and angles reported for a closely related compound (Gowda et al., 2008). The crystal packing of the title compound is stabilized by weak N—H···O and C—H···O intermolecular hydrogen bonds which results in a hydrogen bonded 3-D network (Fig. 2).

Related literature top

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

Experimental top

A solution of 4-nitrobenzoyl chloride (0.01 mol) and 4-bromoaniline (0.01 mol) in anhydrous acetone was refluxed for 4 h. After completion of the reaction, the crude solid product was filtered, washed with water and purified by re-crystallization from ethyl acetate.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed down the a axis; hydrogen bonds are indicated by dashed lines indicate and H-atoms not involved in hydrogen bonding have been excluded for clarity.

N-(4-Bromophenyl)-4-nitrobenzamide top

Crystal data top

C₁₃H₉BrN₂O₃	F(000) = 640
M_r = 321.13	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2434 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2329 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.0°, θ_min = 5.5°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −15→15
T_min = 0.485, T_max = 1.000	l = −20→25
8049 measured reflections

Refinement top

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(F_o²) + (0.0496P)² + 0.6292P] where P = (F_o² + 2F_c²)/3
2434 reflections	(Δ/σ)_max = 0.002
172 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₉BrN₂O₃	V = 1210.24 (3) Å³
M_r = 321.13	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 4.57903 (6) Å	µ = 4.70 mm⁻¹
b = 12.92579 (15) Å	T = 123 K
c = 20.5614 (3) Å	0.48 × 0.12 × 0.07 mm
β = 96.0333 (11)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2434 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2329 reflections with I > 2σ(I)
T_min = 0.485, T_max = 1.000	R_int = 0.025
8049 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.06	Δρ_max = 0.52 e Å⁻³
2434 reflections	Δρ_min = −0.29 e Å⁻³
172 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	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) x−1, y, z; (ii) −x−1, y+1/2, −z+3/2; (iii) −x+1, −y, −z+1; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₉BrN₂O₃
M_r	321.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	4.57903 (6), 12.92579 (15), 20.5614 (3)
β (°)	96.0333 (11)
V (Å³)	1210.24 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.70
Crystal size (mm)	0.48 × 0.12 × 0.07

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.485, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8049, 2434, 2329
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.075, 1.06
No. of reflections	2434
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.29

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···O3^iv	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) x−1, y, z; (ii) −x−1, y+1/2, −z+3/2; (iii) −x+1, −y, −z+1; (iv) x, y+1, z.

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1294. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jagessar, R. C. & Rampersaud, D. (2007). Life Sci. J. 4, 46–49. CAS Google Scholar
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Priya, B. S., Swamy, B. S. N. & Rangapa, K. S. (2005). Bioorg. Med. Chem. 13, 2623–2628. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar