N-(2-Methyl-phen-yl)-2-nitro-benzamide.

In the title compound, C(14)H(12)N(2)O(3), the dihedral angle between the two aromatic rings is 41.48 (5)°. The nitro group is twisted by 24.7 (3)° out of the plane of the aromatic ring to which it is attached. The mol-ecules are connected by N-H⋯O hydrogen bonds into chains running along the a axis.

Related literature

For related literature, see: Igawa et al. (1999 ▶); Jackson et al. (1994 ▶); Makino et al. (2001 ▶, 2003 ▶); Manley et al. (2002 ▶); Zhichkin et al. (2007 ▶); Capdeville et al. (2002 ▶); Ho et al. (2002 ▶).

Experimental

Crystal data

C14H12N2O3

M = 256.26

Orthorhombic,

a = 7.8063 (10) Å

b = 12.2856 (11) Å

c = 13.1353 (13) Å

V = 1259.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 273 (2) K

0.35 × 0.14 × 0.13 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: none

4741 measured reflections

1364 independent reflections

1243 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.077

S = 1.02

1364 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002298/at2536sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002298/at2536Isup2.hkl

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

C14H12N2O3	F000 = 536
Mr = 256.26	Dx = 1.351 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3989 reflections
a = 7.8063 (10) Å	θ = 3.6–25.7º
b = 12.2856 (11) Å	µ = 0.10 mm−1
c = 13.1353 (13) Å	T = 273 (2) K
V = 1259.7 (2) Å3	Needle, light brown
Z = 4	0.35 × 0.14 × 0.13 mm

Stoe IPDSII two-circle diffractometer	1243 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Monochromator: graphite	θmax = 25.5º
T = 273(2) K	θmin = 3.5º
ω scans	h = −8→9
Absorption correction: none	k = −14→12
4741 measured reflections	l = −15→15
1364 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.0696P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.13 e Å−3
1364 reflections	Δρmin = −0.14 e Å−3
178 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (3)
Secondary atom site location: difference Fourier map

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	0.6342 (2)	0.68690 (13)	0.54004 (11)	0.0240 (4)
H1	0.553 (3)	0.726 (2)	0.5746 (17)	0.040 (7)*
C1	0.7172 (2)	0.73801 (15)	0.46407 (13)	0.0227 (4)
O1	0.82960 (19)	0.69697 (10)	0.41024 (10)	0.0277 (3)
N2	0.5272 (2)	0.82075 (14)	0.28700 (12)	0.0302 (4)
O2	0.5146 (3)	0.85091 (14)	0.19817 (11)	0.0495 (5)
O3	0.4810 (2)	0.73064 (12)	0.31740 (11)	0.0388 (4)
C11	0.6745 (2)	0.85748 (16)	0.45063 (13)	0.0239 (4)
C12	0.5996 (3)	0.89811 (16)	0.36185 (14)	0.0251 (4)
C13	0.5832 (3)	1.00790 (17)	0.34180 (16)	0.0341 (5)
H13	0.5322	1.0317	0.2818	0.041*
C14	0.6439 (3)	1.08187 (18)	0.41256 (18)	0.0405 (5)
H14	0.6340	1.1562	0.4004	0.049*
C15	0.7190 (3)	1.04525 (17)	0.50114 (18)	0.0383 (5)
H15	0.7598	1.0952	0.5485	0.046*
C16	0.7347 (3)	0.93358 (17)	0.52071 (16)	0.0321 (5)
H16	0.7856	0.9101	0.5808	0.038*
C21	0.6503 (3)	0.57434 (16)	0.56687 (14)	0.0246 (4)
C22	0.6130 (3)	0.54470 (17)	0.66744 (14)	0.0284 (4)
C23	0.6223 (3)	0.43408 (19)	0.69291 (17)	0.0384 (5)
H23	0.5968	0.4124	0.7590	0.046*
C24	0.6687 (4)	0.35605 (18)	0.62128 (18)	0.0417 (6)
H24	0.6756	0.2831	0.6399	0.050*
C25	0.7045 (3)	0.38710 (17)	0.52281 (17)	0.0392 (5)
H25	0.7353	0.3349	0.4749	0.047*
C26	0.6949 (3)	0.49615 (17)	0.49469 (15)	0.0316 (5)
H26	0.7181	0.5168	0.4280	0.038*
C27	0.5619 (3)	0.6283 (2)	0.74710 (14)	0.0365 (5)
H27A	0.6471	0.6846	0.7501	0.055*
H27B	0.5531	0.5935	0.8124	0.055*
H27C	0.4533	0.6595	0.7292	0.055*

	U11	U22	U33	U12	U13	U23
N1	0.0313 (9)	0.0204 (8)	0.0201 (8)	0.0029 (7)	0.0025 (7)	0.0010 (6)
C1	0.0261 (10)	0.0223 (9)	0.0198 (8)	−0.0011 (8)	−0.0039 (7)	−0.0026 (7)
O1	0.0326 (8)	0.0226 (7)	0.0278 (7)	−0.0013 (6)	0.0060 (6)	−0.0034 (5)
N2	0.0338 (9)	0.0316 (10)	0.0251 (8)	0.0001 (8)	−0.0025 (7)	0.0009 (7)
O2	0.0736 (13)	0.0524 (10)	0.0226 (7)	−0.0003 (10)	−0.0107 (8)	0.0060 (7)
O3	0.0504 (10)	0.0302 (7)	0.0358 (7)	−0.0138 (7)	−0.0059 (7)	−0.0001 (6)
C11	0.0259 (10)	0.0206 (9)	0.0252 (9)	0.0001 (8)	0.0029 (8)	−0.0013 (7)
C12	0.0259 (10)	0.0244 (10)	0.0250 (9)	−0.0034 (8)	0.0018 (8)	0.0009 (7)
C13	0.0388 (12)	0.0262 (11)	0.0373 (10)	0.0009 (9)	0.0015 (10)	0.0096 (9)
C14	0.0439 (13)	0.0210 (10)	0.0565 (14)	0.0021 (10)	−0.0018 (11)	0.0034 (10)
C15	0.0425 (13)	0.0233 (10)	0.0492 (13)	−0.0015 (10)	−0.0036 (11)	−0.0101 (9)
C16	0.0377 (12)	0.0271 (10)	0.0314 (10)	0.0034 (9)	−0.0054 (9)	−0.0050 (8)
C21	0.0274 (10)	0.0224 (9)	0.0242 (8)	0.0002 (8)	−0.0025 (8)	0.0036 (7)
C22	0.0311 (10)	0.0300 (10)	0.0241 (9)	0.0019 (9)	−0.0024 (8)	0.0053 (8)
C23	0.0465 (13)	0.0357 (12)	0.0330 (10)	0.0005 (10)	−0.0003 (10)	0.0134 (9)
C24	0.0532 (14)	0.0230 (10)	0.0490 (12)	0.0001 (11)	0.0022 (12)	0.0116 (10)
C25	0.0522 (14)	0.0231 (10)	0.0422 (11)	−0.0016 (10)	0.0020 (11)	−0.0017 (9)
C26	0.0439 (13)	0.0230 (9)	0.0278 (10)	−0.0016 (9)	0.0016 (9)	0.0020 (8)
C27	0.0451 (13)	0.0436 (13)	0.0209 (9)	0.0077 (11)	0.0032 (9)	0.0031 (9)

N1—C1	1.345 (2)	C15—H15	0.9300
N1—C21	1.433 (2)	C16—H16	0.9300
N1—H1	0.92 (3)	C21—C26	1.394 (3)
C1—O1	1.234 (2)	C21—C22	1.401 (3)
C1—C11	1.515 (3)	C22—C23	1.401 (3)
N2—O2	1.228 (2)	C22—C27	1.519 (3)
N2—O3	1.231 (2)	C23—C24	1.391 (3)
N2—C12	1.480 (3)	C23—H23	0.9300
C11—C16	1.393 (3)	C24—C25	1.377 (3)
C11—C12	1.397 (3)	C24—H24	0.9300
C12—C13	1.380 (3)	C25—C26	1.392 (3)
C13—C14	1.384 (3)	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300
C14—C15	1.379 (3)	C27—H27A	0.9600
C14—H14	0.9300	C27—H27B	0.9600
C15—C16	1.401 (3)	C27—H27C	0.9600
C1—N1—C21	126.20 (17)	C15—C16—H16	119.8
C1—N1—H1	117.5 (15)	C26—C21—C22	120.94 (18)
C21—N1—H1	116.1 (16)	C26—C21—N1	121.32 (16)
O1—C1—N1	125.21 (18)	C22—C21—N1	117.68 (17)
O1—C1—C11	119.02 (17)	C21—C22—C23	117.80 (19)
N1—C1—C11	115.63 (16)	C21—C22—C27	121.89 (18)
O2—N2—O3	123.79 (18)	C23—C22—C27	120.30 (18)
O2—N2—C12	117.91 (17)	C24—C23—C22	121.35 (19)
O3—N2—C12	118.30 (16)	C24—C23—H23	119.3
C16—C11—C12	116.93 (18)	C22—C23—H23	119.3
C16—C11—C1	119.92 (16)	C25—C24—C23	119.8 (2)
C12—C11—C1	122.37 (16)	C25—C24—H24	120.1
C13—C12—C11	123.19 (18)	C23—C24—H24	120.1
C13—C12—N2	117.73 (18)	C24—C25—C26	120.3 (2)
C11—C12—N2	119.03 (17)	C24—C25—H25	119.8
C12—C13—C14	118.8 (2)	C26—C25—H25	119.8
C12—C13—H13	120.6	C25—C26—C21	119.76 (19)
C14—C13—H13	120.6	C25—C26—H26	120.1
C15—C14—C13	119.9 (2)	C21—C26—H26	120.1
C15—C14—H14	120.1	C22—C27—H27A	109.5
C13—C14—H14	120.1	C22—C27—H27B	109.5
C14—C15—C16	120.8 (2)	H27A—C27—H27B	109.5
C14—C15—H15	119.6	C22—C27—H27C	109.5
C16—C15—H15	119.6	H27A—C27—H27C	109.5
C11—C16—C15	120.4 (2)	H27B—C27—H27C	109.5
C11—C16—H16	119.8
C21—N1—C1—O1	−5.4 (3)	C13—C14—C15—C16	−0.1 (4)
C21—N1—C1—C11	178.96 (17)	C12—C11—C16—C15	0.0 (3)
O1—C1—C11—C16	−103.0 (2)	C1—C11—C16—C15	170.1 (2)
N1—C1—C11—C16	72.9 (2)	C14—C15—C16—C11	0.1 (4)
O1—C1—C11—C12	66.5 (3)	C1—N1—C21—C26	−27.7 (3)
N1—C1—C11—C12	−117.6 (2)	C1—N1—C21—C22	154.78 (19)
C16—C11—C12—C13	−0.2 (3)	C26—C21—C22—C23	0.1 (3)
C1—C11—C12—C13	−170.0 (2)	N1—C21—C22—C23	177.60 (19)
C16—C11—C12—N2	−177.46 (18)	C26—C21—C22—C27	−179.2 (2)
C1—C11—C12—N2	12.7 (3)	N1—C21—C22—C27	−1.7 (3)
O2—N2—C12—C13	26.3 (3)	C21—C22—C23—C24	0.7 (3)
O3—N2—C12—C13	−152.8 (2)	C27—C22—C23—C24	−180.0 (2)
O2—N2—C12—C11	−156.3 (2)	C22—C23—C24—C25	−0.8 (4)
O3—N2—C12—C11	24.7 (3)	C23—C24—C25—C26	0.2 (4)
C11—C12—C13—C14	0.2 (3)	C24—C25—C26—C21	0.6 (4)
N2—C12—C13—C14	177.49 (19)	C22—C21—C26—C25	−0.7 (3)
C12—C13—C14—C15	0.0 (3)	N1—C21—C26—C25	−178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.92 (3)	1.99 (3)	2.849 (2)	155 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.92 (3)	1.99 (3)	2.849 (2)	155 (2)

Symmetry code: (i) .