N-(2-Nitro-phen-yl)benzamide.

In the title compound, C(13)H(10)N(2)O(3), the central C-C(=O)-N-C amide unit makes dihedral angles of 21.68 (4) and 19.08 (4)°, respectively, with the phenyl and nitro-benzene rings. The two aromatic rings are inclined at 3.74 (3)° and the nitro group is skewed out of the attached benzene ring plane by 18.55 (8)°. An intra-molecular N-H⋯O inter-action to an O atom of the nitro substituent generates an S(6) ring motif. In the crystal, C-H⋯O contacts generate two centrosymmetric ring systems with R(2) (2)(14) and R(2) (2)(20) graph-set motifs, forming zigzag chains down the a axis. π-π inter-actions between adjacent phenyl and nitro-benzene rings [centroid-centroid distance = 3.6849 (6) Å] also form centrosymmetric dimers. These and an additional C-H⋯O hydrogen bond generate an extensive three-dimensional network structure.

Related literature

For the biological activity of benzamide derivatives see Saeed et al. (2008 ▶). For related structures, see: Cronin et al. (2000 ▶); Glidewell et al. (2004 ▶); Wardell et al. (2005 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H10N2O3

M = 242.23

Monoclinic,

a = 7.2061 (5) Å

b = 7.4253 (5) Å

c = 20.6031 (13) Å

β = 93.560 (4)°

V = 1100.29 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 89 K

0.24 × 0.17 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.852, T max = 0.991

20195 measured reflections

3948 independent reflections

3098 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.06

3948 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker 2006 ▶); cell refinement: APEX2 and SAINT (Bruker 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024271/at2824sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024271/at2824Isup2.hkl

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

C13H10N2O3	F(000) = 504
Mr = 242.23	Dx = 1.462 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4696 reflections
a = 7.2061 (5) Å	θ = 2.8–31.8°
b = 7.4253 (5) Å	µ = 0.11 mm−1
c = 20.6031 (13) Å	T = 89 K
β = 93.560 (4)°	Plate, colourless
V = 1100.29 (13) Å3	0.24 × 0.17 × 0.09 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3948 independent reflections
Radiation source: fine-focus sealed tube	3098 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω scans	θmax = 33.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −10→10
Tmin = 0.852, Tmax = 0.991	k = −11→10
20195 measured reflections	l = −30→30

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.2001P] where P = (Fo2 + 2Fc2)/3
3948 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.27 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
N1	0.73812 (11)	0.03317 (11)	0.50049 (4)	0.01315 (16)
H1N	0.678 (2)	−0.064 (2)	0.5129 (7)	0.031 (4)*
O1	0.87401 (11)	0.16410 (10)	0.41448 (4)	0.01879 (17)
C1	0.78498 (13)	0.04075 (12)	0.43690 (4)	0.01259 (17)
C2	0.71690 (13)	−0.11570 (12)	0.39614 (4)	0.01239 (17)
C3	0.70064 (14)	−0.09052 (13)	0.32883 (5)	0.01564 (19)
H3	0.7315	0.0226	0.3109	0.019*
C4	0.63950 (14)	−0.23021 (14)	0.28797 (5)	0.01771 (19)
H4	0.6275	−0.2120	0.2423	0.021*
C5	0.59588 (14)	−0.39666 (14)	0.31405 (5)	0.0176 (2)
H5	0.5543	−0.4921	0.2861	0.021*
C6	0.61305 (14)	−0.42356 (13)	0.38095 (5)	0.01679 (19)
H6	0.5840	−0.5376	0.3986	0.020*
C7	0.67274 (13)	−0.28349 (13)	0.42198 (5)	0.01451 (18)
H7	0.6836	−0.3018	0.4677	0.017*
C8	0.78625 (12)	0.15306 (12)	0.55126 (4)	0.01171 (17)
C9	0.78085 (13)	0.09917 (12)	0.61677 (4)	0.01252 (17)
N2	0.72463 (12)	−0.08197 (11)	0.63520 (4)	0.01487 (17)
O2	0.76511 (13)	−0.13362 (11)	0.69076 (4)	0.0268 (2)
O3	0.63473 (11)	−0.17725 (10)	0.59477 (3)	0.01818 (16)
C10	0.82755 (13)	0.21653 (14)	0.66792 (5)	0.01574 (19)
H10	0.8235	0.1765	0.7116	0.019*
C11	0.87973 (14)	0.39107 (14)	0.65503 (5)	0.0184 (2)
H11	0.9112	0.4720	0.6897	0.022*
C12	0.88585 (14)	0.44738 (13)	0.59089 (5)	0.01733 (19)
H12	0.9218	0.5675	0.5820	0.021*
C13	0.84023 (13)	0.33090 (12)	0.53965 (5)	0.01466 (18)
H13	0.8457	0.3723	0.4962	0.018*

	U11	U22	U33	U12	U13	U23
N1	0.0166 (4)	0.0113 (4)	0.0116 (3)	−0.0039 (3)	0.0014 (3)	−0.0001 (3)
O1	0.0249 (4)	0.0136 (3)	0.0186 (3)	−0.0056 (3)	0.0078 (3)	−0.0007 (3)
C1	0.0126 (4)	0.0114 (4)	0.0139 (4)	0.0010 (3)	0.0017 (3)	0.0002 (3)
C2	0.0119 (4)	0.0119 (4)	0.0133 (4)	0.0005 (3)	0.0010 (3)	−0.0004 (3)
C3	0.0179 (4)	0.0153 (4)	0.0140 (4)	0.0009 (3)	0.0023 (3)	0.0007 (3)
C4	0.0190 (5)	0.0201 (5)	0.0139 (4)	0.0021 (4)	0.0000 (3)	−0.0023 (3)
C5	0.0149 (4)	0.0179 (5)	0.0198 (4)	0.0004 (3)	−0.0011 (3)	−0.0060 (4)
C6	0.0162 (4)	0.0127 (4)	0.0214 (5)	−0.0012 (3)	0.0006 (3)	−0.0013 (3)
C7	0.0154 (4)	0.0128 (4)	0.0153 (4)	−0.0001 (3)	0.0010 (3)	0.0005 (3)
C8	0.0102 (4)	0.0115 (4)	0.0135 (4)	0.0003 (3)	0.0009 (3)	−0.0008 (3)
C9	0.0126 (4)	0.0109 (4)	0.0140 (4)	0.0005 (3)	0.0009 (3)	−0.0002 (3)
N2	0.0181 (4)	0.0137 (4)	0.0130 (3)	0.0016 (3)	0.0023 (3)	0.0012 (3)
O2	0.0434 (5)	0.0226 (4)	0.0139 (3)	0.0000 (3)	−0.0016 (3)	0.0063 (3)
O3	0.0239 (4)	0.0138 (3)	0.0168 (3)	−0.0041 (3)	0.0013 (3)	0.0000 (2)
C10	0.0149 (4)	0.0179 (4)	0.0143 (4)	0.0022 (3)	−0.0001 (3)	−0.0030 (3)
C11	0.0158 (4)	0.0182 (5)	0.0212 (5)	−0.0008 (4)	0.0016 (4)	−0.0082 (4)
C12	0.0148 (4)	0.0125 (4)	0.0252 (5)	−0.0023 (3)	0.0054 (4)	−0.0038 (4)
C13	0.0145 (4)	0.0117 (4)	0.0180 (4)	−0.0009 (3)	0.0035 (3)	0.0000 (3)

N1—C1	1.3742 (11)	C7—H7	0.9500
N1—C8	1.4006 (12)	C8—C13	1.4014 (13)
N1—H1N	0.887 (16)	C8—C9	1.4107 (13)
O1—C1	1.2250 (11)	C9—C10	1.3925 (13)
C1—C2	1.4981 (13)	C9—N2	1.4617 (12)
C2—C3	1.3971 (12)	N2—O2	1.2251 (10)
C2—C7	1.3992 (13)	N2—O3	1.2439 (11)
C3—C4	1.3902 (14)	C10—C11	1.3799 (14)
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.3915 (15)	C11—C12	1.3893 (15)
C4—H4	0.9500	C11—H11	0.9500
C5—C6	1.3906 (14)	C12—C13	1.3883 (13)
C5—H5	0.9500	C12—H12	0.9500
C6—C7	1.3914 (13)	C13—H13	0.9500
C6—H6	0.9500
C1—N1—C8	128.45 (8)	C2—C7—H7	119.9
C1—N1—H1N	117.4 (10)	N1—C8—C13	122.01 (8)
C8—N1—H1N	113.9 (10)	N1—C8—C9	120.93 (8)
O1—C1—N1	123.75 (9)	C13—C8—C9	117.06 (8)
O1—C1—C2	121.96 (8)	C10—C9—C8	121.79 (9)
N1—C1—C2	114.29 (8)	C10—C9—N2	115.92 (8)
C3—C2—C7	119.32 (9)	C8—C9—N2	122.29 (8)
C3—C2—C1	117.20 (8)	O2—N2—O3	122.11 (9)
C7—C2—C1	123.47 (8)	O2—N2—C9	118.49 (8)
C4—C3—C2	120.34 (9)	O3—N2—C9	119.38 (8)
C4—C3—H3	119.8	C11—C10—C9	119.87 (9)
C2—C3—H3	119.8	C11—C10—H10	120.1
C3—C4—C5	119.97 (9)	C9—C10—H10	120.1
C3—C4—H4	120.0	C10—C11—C12	119.39 (9)
C5—C4—H4	120.0	C10—C11—H11	120.3
C6—C5—C4	120.13 (9)	C12—C11—H11	120.3
C6—C5—H5	119.9	C13—C12—C11	121.05 (9)
C4—C5—H5	119.9	C13—C12—H12	119.5
C5—C6—C7	119.99 (9)	C11—C12—H12	119.5
C5—C6—H6	120.0	C12—C13—C8	120.83 (9)
C7—C6—H6	120.0	C12—C13—H13	119.6
C6—C7—C2	120.23 (9)	C8—C13—H13	119.6
C6—C7—H7	119.9

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.887 (16)	1.927 (15)	2.6361 (11)	135.7 (13)
C10—H10···O2i	0.95	2.57	3.2254 (12)	126
C6—H6···O3ii	0.95	2.65	3.5122 (12)	151
C12—H12···O1iii	0.95	2.48	3.3695 (12)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.887 (16)	1.927 (15)	2.6361 (11)	135.7 (13)
C10—H10⋯O2i	0.95	2.57	3.2254 (12)	126
C6—H6⋯O3ii	0.95	2.65	3.5122 (12)	151
C12—H12⋯O1iii	0.95	2.48	3.3695 (12)	157

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