4-Anilino-3-nitro-benzonitrile.

In the title compound, C(13)H(9)N(3)O(2), the aromatic rings are twisted with respect to each other, making a dihedral angle of 49.41 (9)°. The nitro group and the nitrile group are nearly in the plane of the benzonitrile ring, the largest deviation from the plane being 0.123 (1) Å. There is an intra-molecular N-H⋯O hydrogen bond forming an S(6) ring. Weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a chain parallel to the c axis. Futhermore, slipped π-π inter-actions between symmetry-related phenyl rings [centroid-centroid distance 3.808 (1) Å, inter-planar distance 3.544 (8) Å with an offset of 21.5°] stabilize the structure.

Related literature

For the synthesis of the title compound, see: Schelz & Inst (1978 ▶). For related structures, see: McWilliam et al. (2001 ▶); Li, Liu et al. (2009 ▶); Li, Wu et al. (2009 ▶). For discussion of hydrogen bonding, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9N3O2

M = 239.23

Monoclinic,

a = 14.066 (3) Å

b = 7.4290 (15) Å

c = 11.652 (2) Å

β = 109.04 (3)°

V = 1151.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.30 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.972, T max = 0.990

4199 measured reflections

2082 independent reflections

1546 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.04

2082 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043862/dn2613sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043862/dn2613Isup2.hkl

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

C13H9N3O2	F(000) = 496
Mr = 239.23	Dx = 1.381 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 14.066 (3) Å	θ = 9–13°
b = 7.4290 (15) Å	µ = 0.10 mm−1
c = 11.652 (2) Å	T = 293 K
β = 109.04 (3)°	Block, colourless
V = 1151.0 (4) Å3	0.30 × 0.30 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1546 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 25.3°, θmin = 1.5°
ω/2θ scans	h = −16→15
Absorption correction: ψ scan (North et al., 1968)	k = −8→8
Tmin = 0.972, Tmax = 0.990	l = 0→13
4199 measured reflections	3 standard reflections every 200 reflections
2082 independent reflections	intensity decay: 1%

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.1451P] where P = (Fo2 + 2Fc2)/3
2082 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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 > 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
O1	0.91767 (8)	0.4271 (2)	0.39718 (10)	0.0665 (4)
O2	0.84253 (9)	0.43363 (19)	0.20463 (10)	0.0659 (4)
N1	0.82164 (10)	0.5168 (2)	0.54802 (11)	0.0545 (4)
H1	0.8774	0.4845	0.5388	0.065*
N2	0.84229 (10)	0.45587 (19)	0.30832 (11)	0.0485 (4)
N3	0.43509 (11)	0.6904 (2)	0.03546 (14)	0.0699 (5)
C1	0.74708 (13)	0.4539 (2)	0.70743 (15)	0.0570 (5)
H1B	0.6921	0.3979	0.6517	0.068*
C2	0.75504 (15)	0.4625 (3)	0.82822 (17)	0.0669 (5)
H2A	0.7042	0.4143	0.8535	0.080*
C3	0.83667 (16)	0.5411 (3)	0.91186 (16)	0.0695 (6)
H3A	0.8414	0.5451	0.9933	0.083*
C4	0.91129 (15)	0.6136 (3)	0.87473 (16)	0.0656 (5)
H4A	0.9671	0.6659	0.9314	0.079*
C5	0.90432 (12)	0.6097 (3)	0.75389 (14)	0.0537 (4)
H5A	0.9548	0.6605	0.7290	0.064*
C6	0.82202 (11)	0.5299 (2)	0.67003 (13)	0.0463 (4)
C7	0.74482 (11)	0.5487 (2)	0.44502 (13)	0.0438 (4)
C8	0.65218 (12)	0.6207 (2)	0.44808 (14)	0.0489 (4)
H8A	0.6447	0.6444	0.5230	0.059*
C9	0.57426 (12)	0.6561 (2)	0.34586 (14)	0.0506 (4)
H9A	0.5150	0.7039	0.3520	0.061*
C10	0.58206 (11)	0.6214 (2)	0.23110 (14)	0.0461 (4)
C11	0.67092 (11)	0.5533 (2)	0.22313 (13)	0.0455 (4)
H11A	0.6771	0.5300	0.1474	0.055*
C12	0.75095 (11)	0.5196 (2)	0.32739 (13)	0.0432 (4)
C13	0.49993 (12)	0.6596 (2)	0.12224 (15)	0.0524 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0436 (7)	0.1033 (11)	0.0496 (7)	0.0174 (7)	0.0112 (5)	−0.0019 (6)
O2	0.0553 (7)	0.1003 (11)	0.0471 (7)	0.0071 (7)	0.0237 (6)	−0.0053 (6)
N1	0.0437 (7)	0.0796 (11)	0.0403 (7)	0.0117 (7)	0.0140 (6)	0.0013 (7)
N2	0.0431 (7)	0.0617 (9)	0.0421 (7)	0.0019 (7)	0.0157 (6)	−0.0028 (6)
N3	0.0545 (9)	0.0920 (13)	0.0557 (9)	0.0140 (9)	0.0076 (8)	0.0037 (9)
C1	0.0556 (10)	0.0621 (11)	0.0535 (10)	−0.0002 (9)	0.0182 (8)	0.0053 (9)
C2	0.0700 (12)	0.0752 (13)	0.0661 (12)	0.0131 (11)	0.0369 (10)	0.0185 (10)
C3	0.0884 (15)	0.0803 (14)	0.0438 (10)	0.0311 (12)	0.0268 (10)	0.0111 (9)
C4	0.0634 (11)	0.0753 (13)	0.0466 (10)	0.0174 (10)	0.0022 (9)	−0.0035 (9)
C5	0.0428 (9)	0.0686 (11)	0.0476 (9)	0.0092 (8)	0.0120 (7)	0.0026 (8)
C6	0.0449 (8)	0.0540 (10)	0.0394 (8)	0.0119 (8)	0.0130 (7)	0.0038 (7)
C7	0.0430 (8)	0.0468 (9)	0.0418 (8)	−0.0007 (7)	0.0140 (7)	−0.0001 (7)
C8	0.0485 (9)	0.0578 (10)	0.0431 (9)	0.0042 (8)	0.0189 (7)	−0.0009 (8)
C9	0.0431 (9)	0.0561 (10)	0.0543 (10)	0.0058 (8)	0.0181 (8)	0.0022 (8)
C10	0.0395 (8)	0.0509 (10)	0.0450 (9)	−0.0007 (7)	0.0102 (7)	0.0020 (7)
C11	0.0461 (9)	0.0509 (10)	0.0394 (8)	−0.0027 (7)	0.0140 (7)	−0.0013 (7)
C12	0.0389 (8)	0.0472 (9)	0.0442 (8)	0.0013 (7)	0.0144 (7)	−0.0013 (7)
C13	0.0449 (9)	0.0615 (11)	0.0502 (9)	0.0041 (8)	0.0148 (8)	0.0021 (8)

O1—N2	1.2352 (16)	C4—C5	1.379 (2)
O2—N2	1.2206 (16)	C4—H4A	0.9300
N1—C7	1.3483 (18)	C5—C6	1.382 (2)
N1—C6	1.4232 (19)	C5—H5A	0.9300
N1—H1	0.8600	C7—C12	1.418 (2)
N2—C12	1.4529 (19)	C7—C8	1.420 (2)
N3—C13	1.142 (2)	C8—C9	1.356 (2)
C1—C2	1.377 (2)	C8—H8A	0.9300
C1—C6	1.385 (2)	C9—C10	1.401 (2)
C1—H1B	0.9300	C9—H9A	0.9300
C2—C3	1.371 (3)	C10—C11	1.379 (2)
C2—H2A	0.9300	C10—C13	1.438 (2)
C3—C4	1.369 (3)	C11—C12	1.383 (2)
C3—H3A	0.9300	C11—H11A	0.9300
C7—N1—C6	128.16 (14)	C5—C6—N1	117.71 (15)
C7—N1—H1	115.9	C1—C6—N1	122.08 (15)
C6—N1—H1	115.9	N1—C7—C12	123.37 (14)
O2—N2—O1	121.83 (13)	N1—C7—C8	121.29 (14)
O2—N2—C12	118.93 (13)	C12—C7—C8	115.30 (14)
O1—N2—C12	119.24 (13)	C9—C8—C7	122.46 (15)
C2—C1—C6	119.09 (17)	C9—C8—H8A	118.8
C2—C1—H1B	120.5	C7—C8—H8A	118.8
C6—C1—H1B	120.5	C8—C9—C10	120.70 (15)
C3—C2—C1	121.11 (18)	C8—C9—H9A	119.7
C3—C2—H2A	119.4	C10—C9—H9A	119.7
C1—C2—H2A	119.4	C11—C10—C9	119.11 (14)
C4—C3—C2	119.57 (17)	C11—C10—C13	119.86 (15)
C4—C3—H3A	120.2	C9—C10—C13	121.01 (15)
C2—C3—H3A	120.2	C10—C11—C12	120.19 (15)
C3—C4—C5	120.51 (18)	C10—C11—H11A	119.9
C3—C4—H4A	119.7	C12—C11—H11A	119.9
C5—C4—H4A	119.7	C11—C12—C7	122.20 (14)
C4—C5—C6	119.68 (18)	C11—C12—N2	115.57 (13)
C4—C5—H5A	120.2	C7—C12—N2	122.22 (13)
C6—C5—H5A	120.2	N3—C13—C10	179.6 (2)
C5—C6—C1	120.02 (15)
C6—C1—C2—C3	−1.5 (3)	C8—C9—C10—C11	−1.1 (3)
C1—C2—C3—C4	0.5 (3)	C8—C9—C10—C13	−179.63 (16)
C2—C3—C4—C5	0.7 (3)	C9—C10—C11—C12	0.1 (2)
C3—C4—C5—C6	−0.8 (3)	C13—C10—C11—C12	178.70 (15)
C4—C5—C6—C1	−0.1 (3)	C10—C11—C12—C7	1.5 (2)
C4—C5—C6—N1	−175.33 (16)	C10—C11—C12—N2	−177.32 (14)
C2—C1—C6—C5	1.3 (3)	N1—C7—C12—C11	179.94 (15)
C2—C1—C6—N1	176.26 (16)	C8—C7—C12—C11	−2.1 (2)
C7—N1—C6—C5	−137.13 (18)	N1—C7—C12—N2	−1.3 (2)
C7—N1—C6—C1	47.8 (3)	C8—C7—C12—N2	176.63 (15)
C6—N1—C7—C12	−175.60 (16)	O2—N2—C12—C11	−1.2 (2)
C6—N1—C7—C8	6.6 (3)	O1—N2—C12—C11	178.27 (15)
N1—C7—C8—C9	179.15 (16)	O2—N2—C12—C7	180.00 (15)
C12—C7—C8—C9	1.2 (2)	O1—N2—C12—C7	−0.6 (2)
C7—C8—C9—C10	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.96	2.6280 (18)	134
C3—H3A···O2i	0.93	2.59	3.478 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.96	2.6280 (18)	134
C3—H3A⋯O2i	0.93	2.59	3.478 (2)	159

Symmetry code: (i) .