4-Anilino-3-nitro-N-phenyl-benzamide.

In the title compound, C(19)H(15)N(3)O(3), the anilino and benzamide rings make dihedral angles of 10.66 (16) and 50.39 (16)°, respectively, with the nitro-substituted benzene ring. The nitro group is slightly twisted by 11.49 (17)° with respect to the attached benzene ring. There is an intra-molecular N-H⋯O hydrogen bond forming an S(6) ring. In the crystal, weak inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a chain parallel to the b axis. Futhermore, weak slipped π-π inter-actions [centroid-centroid distance = 3.819 (2) Å, inter-planar distance = 3.567 Å and offset angle [how is the offset angle defined?] = 21°] between the anilino ring and its symmetry-related counterpart may help to stabilize the packing.

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

C19H15N3O3

M = 333.34

Triclinic,

a = 7.7930 (16) Å

b = 8.1580 (16) Å

c = 12.788 (3) Å

α = 84.73 (3)°

β = 83.82 (3)°

γ = 73.58 (3)°

V = 773.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.971, T max = 0.990

3037 measured reflections

2809 independent reflections

1913 reflections with I > 2σ(I)

R int = 0.069

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.173

S = 1.07

2809 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.27 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/S1600536810043849/dn2614sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043849/dn2614Isup2.hkl

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

C19H15N3O3	Z = 2
Mr = 333.34	F(000) = 348
Triclinic, P1	Dx = 1.431 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7930 (16) Å	Cell parameters from 25 reflections
b = 8.1580 (16) Å	θ = 9–13°
c = 12.788 (3) Å	µ = 0.10 mm−1
α = 84.73 (3)°	T = 293 K
β = 83.82 (3)°	Block, colourless
γ = 73.58 (3)°	0.30 × 0.20 × 0.10 mm
V = 773.7 (3) Å3

Enraf–Nonius CAD-4 diffractometer	1913 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
graphite	θmax = 25.3°, θmin = 1.6°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.971, Tmax = 0.990	l = −15→15
3037 measured reflections	3 standard reflections every 200 reflections
2809 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0726P)2 + 0.3362P] where P = (Fo2 + 2Fc2)/3
2809 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.27 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	0.1624 (3)	0.4949 (3)	0.34191 (17)	0.0597 (7)
O2	0.4401 (3)	−0.0652 (3)	0.68488 (17)	0.0595 (7)
O3	0.3047 (3)	−0.0231 (3)	0.54356 (17)	0.0552 (6)
N1	0.1661 (3)	0.7456 (3)	0.40167 (18)	0.0439 (6)
H1	0.1892	0.7898	0.4552	0.053*
N2	0.3633 (3)	0.0321 (3)	0.61399 (18)	0.0408 (6)
N3	0.4299 (3)	0.2000 (3)	0.79278 (18)	0.0442 (6)
H3	0.4810	0.0922	0.7892	0.053*
C1	0.0361 (4)	0.8190 (4)	0.2304 (2)	0.0442 (7)
H1B	0.0293	0.7078	0.2265	0.053*
C2	−0.0237 (4)	0.9424 (4)	0.1516 (2)	0.0525 (8)
H2A	−0.0742	0.9143	0.0955	0.063*
C3	−0.0102 (5)	1.1066 (4)	0.1543 (3)	0.0562 (9)
H3B	−0.0473	1.1875	0.0993	0.067*
C4	0.0583 (5)	1.1499 (4)	0.2389 (3)	0.0535 (8)
H4A	0.0663	1.2609	0.2420	0.064*
C5	0.1152 (4)	1.0284 (4)	0.3193 (2)	0.0486 (8)
H5A	0.1601	1.0588	0.3769	0.058*
C6	0.1066 (4)	0.8620 (4)	0.3157 (2)	0.0386 (7)
C7	0.1915 (4)	0.5740 (3)	0.4114 (2)	0.0377 (7)
C8	0.2585 (4)	0.4838 (3)	0.5121 (2)	0.0372 (7)
C9	0.2942 (4)	0.5618 (4)	0.5980 (2)	0.0436 (7)
H9A	0.2794	0.6794	0.5932	0.052*
C10	0.3501 (4)	0.4676 (4)	0.6883 (2)	0.0431 (7)
H10A	0.3721	0.5233	0.7435	0.052*
C11	0.3756 (4)	0.2896 (3)	0.7005 (2)	0.0364 (6)
C12	0.3430 (4)	0.2137 (3)	0.6127 (2)	0.0361 (6)
C13	0.2860 (4)	0.3091 (3)	0.5223 (2)	0.0372 (6)
H13A	0.2654	0.2539	0.4664	0.045*
C14	0.4108 (4)	0.2654 (3)	0.8927 (2)	0.0371 (7)
C15	0.2639 (4)	0.3943 (4)	0.9262 (2)	0.0450 (7)
H15A	0.1758	0.4464	0.8809	0.054*
C16	0.2481 (4)	0.4458 (4)	1.0272 (2)	0.0537 (8)
H16A	0.1494	0.5340	1.0490	0.064*
C17	0.3752 (5)	0.3695 (5)	1.0967 (2)	0.0570 (9)
H17A	0.3623	0.4045	1.1650	0.068*
C18	0.5225 (5)	0.2398 (5)	1.0630 (3)	0.0563 (9)
H18A	0.6098	0.1869	1.1088	0.068*
C19	0.5402 (4)	0.1891 (4)	0.9619 (2)	0.0454 (7)
H19A	0.6401	0.1025	0.9397	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.0943 (18)	0.0402 (12)	0.0486 (13)	−0.0195 (12)	−0.0183 (12)	−0.0065 (10)
O2	0.0869 (18)	0.0349 (12)	0.0525 (13)	−0.0051 (11)	−0.0210 (12)	0.0004 (10)
O3	0.0802 (17)	0.0388 (12)	0.0546 (14)	−0.0245 (11)	−0.0164 (12)	−0.0064 (10)
N1	0.0598 (16)	0.0353 (13)	0.0422 (14)	−0.0165 (12)	−0.0180 (12)	−0.0038 (11)
N2	0.0497 (15)	0.0350 (13)	0.0375 (13)	−0.0117 (11)	−0.0010 (12)	−0.0049 (11)
N3	0.0540 (16)	0.0363 (13)	0.0406 (14)	−0.0066 (11)	−0.0099 (12)	−0.0061 (11)
C1	0.0492 (18)	0.0436 (17)	0.0429 (17)	−0.0158 (14)	−0.0079 (14)	−0.0048 (13)
C2	0.055 (2)	0.058 (2)	0.0457 (18)	−0.0143 (16)	−0.0132 (15)	−0.0045 (15)
C3	0.064 (2)	0.0492 (19)	0.052 (2)	−0.0109 (16)	−0.0117 (16)	0.0071 (15)
C4	0.065 (2)	0.0389 (17)	0.059 (2)	−0.0170 (16)	−0.0149 (17)	0.0041 (15)
C5	0.059 (2)	0.0436 (17)	0.0498 (18)	−0.0203 (15)	−0.0182 (15)	−0.0015 (14)
C6	0.0376 (15)	0.0391 (16)	0.0409 (16)	−0.0136 (13)	−0.0034 (12)	−0.0023 (12)
C7	0.0404 (16)	0.0384 (16)	0.0366 (15)	−0.0134 (13)	−0.0020 (12)	−0.0084 (12)
C8	0.0412 (16)	0.0349 (15)	0.0379 (15)	−0.0145 (12)	−0.0020 (13)	−0.0029 (12)
C9	0.0564 (19)	0.0315 (15)	0.0464 (17)	−0.0179 (14)	0.0005 (14)	−0.0080 (13)
C10	0.0555 (19)	0.0429 (17)	0.0384 (16)	−0.0231 (14)	−0.0077 (14)	−0.0070 (13)
C11	0.0345 (15)	0.0395 (15)	0.0358 (15)	−0.0110 (12)	0.0002 (12)	−0.0063 (12)
C12	0.0391 (16)	0.0310 (14)	0.0385 (15)	−0.0118 (12)	0.0032 (12)	−0.0057 (12)
C13	0.0437 (16)	0.0351 (15)	0.0360 (15)	−0.0135 (12)	−0.0043 (12)	−0.0094 (12)
C14	0.0410 (16)	0.0370 (15)	0.0372 (15)	−0.0165 (13)	−0.0052 (13)	−0.0013 (12)
C15	0.0409 (17)	0.0485 (18)	0.0460 (18)	−0.0114 (14)	−0.0071 (14)	−0.0048 (14)
C16	0.052 (2)	0.059 (2)	0.0501 (19)	−0.0150 (16)	0.0036 (16)	−0.0168 (16)
C17	0.072 (2)	0.072 (2)	0.0406 (18)	−0.039 (2)	−0.0055 (17)	−0.0085 (16)
C18	0.058 (2)	0.070 (2)	0.0489 (19)	−0.0291 (18)	−0.0169 (16)	0.0079 (17)
C19	0.0445 (17)	0.0489 (18)	0.0453 (17)	−0.0165 (14)	−0.0077 (14)	0.0009 (14)

O1—C7	1.220 (3)	C7—C8	1.492 (4)
O2—N2	1.236 (3)	C8—C13	1.377 (4)
O3—N2	1.225 (3)	C8—C9	1.408 (4)
N1—C7	1.353 (3)	C9—C10	1.368 (4)
N1—C6	1.412 (3)	C9—H9A	0.9300
N1—H1	0.8600	C10—C11	1.405 (4)
N2—C12	1.443 (3)	C10—H10A	0.9300
N3—C11	1.371 (3)	C11—C12	1.410 (4)
N3—C14	1.407 (3)	C12—C13	1.374 (4)
N3—H3	0.8600	C13—H13A	0.9300
C1—C2	1.377 (4)	C14—C15	1.377 (4)
C1—C6	1.387 (4)	C14—C19	1.387 (4)
C1—H1B	0.9300	C15—C16	1.377 (4)
C2—C3	1.377 (4)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.378 (4)
C3—C4	1.372 (4)	C16—H16A	0.9300
C3—H3B	0.9300	C17—C18	1.383 (5)
C4—C5	1.378 (4)	C17—H17A	0.9300
C4—H4A	0.9300	C18—C19	1.374 (4)
C5—C6	1.383 (4)	C18—H18A	0.9300
C5—H5A	0.9300	C19—H19A	0.9300
C7—N1—C6	128.9 (2)	C10—C9—C8	121.1 (3)
C7—N1—H1	115.6	C10—C9—H9A	119.5
C6—N1—H1	115.6	C8—C9—H9A	119.5
O3—N2—O2	121.0 (2)	C9—C10—C11	122.4 (3)
O3—N2—C12	119.0 (2)	C9—C10—H10A	118.8
O2—N2—C12	120.0 (2)	C11—C10—H10A	118.8
C11—N3—C14	127.0 (2)	N3—C11—C10	120.6 (2)
C11—N3—H3	116.5	N3—C11—C12	123.9 (3)
C14—N3—H3	116.5	C10—C11—C12	115.5 (3)
C2—C1—C6	119.4 (3)	C13—C12—C11	121.8 (2)
C2—C1—H1B	120.3	C13—C12—N2	116.5 (2)
C6—C1—H1B	120.3	C11—C12—N2	121.7 (2)
C1—C2—C3	121.3 (3)	C12—C13—C8	122.0 (2)
C1—C2—H2A	119.4	C12—C13—H13A	119.0
C3—C2—H2A	119.4	C8—C13—H13A	119.0
C4—C3—C2	119.4 (3)	C15—C14—C19	119.1 (3)
C4—C3—H3B	120.3	C15—C14—N3	122.6 (3)
C2—C3—H3B	120.3	C19—C14—N3	118.2 (3)
C3—C4—C5	119.8 (3)	C16—C15—C14	119.7 (3)
C3—C4—H4A	120.1	C16—C15—H15A	120.1
C5—C4—H4A	120.1	C14—C15—H15A	120.1
C4—C5—C6	121.1 (3)	C15—C16—C17	121.5 (3)
C4—C5—H5A	119.5	C15—C16—H16A	119.3
C6—C5—H5A	119.5	C17—C16—H16A	119.3
C5—C6—C1	118.9 (3)	C16—C17—C18	118.7 (3)
C5—C6—N1	117.6 (2)	C16—C17—H17A	120.6
C1—C6—N1	123.4 (2)	C18—C17—H17A	120.6
O1—C7—N1	122.4 (3)	C19—C18—C17	120.1 (3)
O1—C7—C8	120.9 (3)	C19—C18—H18A	119.9
N1—C7—C8	116.7 (2)	C17—C18—H18A	119.9
C13—C8—C9	117.2 (3)	C18—C19—C14	120.8 (3)
C13—C8—C7	117.0 (2)	C18—C19—H19A	119.6
C9—C8—C7	125.8 (2)	C14—C19—H19A	119.6
C6—C1—C2—C3	1.9 (5)	N3—C11—C12—C13	179.0 (3)
C1—C2—C3—C4	−2.3 (5)	C10—C11—C12—C13	−1.4 (4)
C2—C3—C4—C5	1.0 (5)	N3—C11—C12—N2	0.6 (4)
C3—C4—C5—C6	0.8 (5)	C10—C11—C12—N2	−179.8 (2)
C4—C5—C6—C1	−1.3 (5)	O3—N2—C12—C13	−10.7 (4)
C4—C5—C6—N1	−179.4 (3)	O2—N2—C12—C13	168.6 (3)
C2—C1—C6—C5	−0.1 (4)	O3—N2—C12—C11	167.7 (3)
C2—C1—C6—N1	178.0 (3)	O2—N2—C12—C11	−12.9 (4)
C7—N1—C6—C5	−171.2 (3)	C11—C12—C13—C8	0.4 (4)
C7—N1—C6—C1	10.7 (5)	N2—C12—C13—C8	178.8 (2)
C6—N1—C7—O1	−0.6 (5)	C9—C8—C13—C12	1.0 (4)
C6—N1—C7—C8	179.1 (3)	C7—C8—C13—C12	−178.3 (2)
O1—C7—C8—C13	0.2 (4)	C11—N3—C14—C15	35.4 (4)
N1—C7—C8—C13	−179.5 (3)	C11—N3—C14—C19	−148.7 (3)
O1—C7—C8—C9	−179.0 (3)	C19—C14—C15—C16	0.3 (4)
N1—C7—C8—C9	1.2 (4)	N3—C14—C15—C16	176.2 (3)
C13—C8—C9—C10	−1.3 (4)	C14—C15—C16—C17	−0.9 (5)
C7—C8—C9—C10	177.9 (3)	C15—C16—C17—C18	0.8 (5)
C8—C9—C10—C11	0.2 (5)	C16—C17—C18—C19	0.0 (5)
C14—N3—C11—C10	22.4 (4)	C17—C18—C19—C14	−0.5 (5)
C14—N3—C11—C12	−158.0 (3)	C15—C14—C19—C18	0.4 (4)
C9—C10—C11—N3	−179.2 (3)	N3—C14—C19—C18	−175.6 (3)
C9—C10—C11—C12	1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.39	3.198 (3)	156
N3—H3···O2	0.86	2.04	2.649 (3)	127
C5—H5A···O3i	0.93	2.47	3.305 (4)	150
C9—H9A···O3i	0.93	2.51	3.416 (4)	165
C1—H1B···O1	0.93	2.26	2.851 (4)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.39	3.198 (3)	156
N3—H3⋯O2	0.86	2.04	2.649 (3)	127
C5—H5A⋯O3i	0.93	2.47	3.305 (4)	150
C9—H9A⋯O3i	0.93	2.51	3.416 (4)	165
C1—H1B⋯O1	0.93	2.26	2.851 (4)	121

Symmetry code: (i) .