N-(4-Nitro-phen-yl)cinnamamide.

In the mol-ecule of the title compound, C(15)H(12)N(2)O(3), the dihedral angle between the rings is 3.04 (8)°. The central NOC(3) fragment is planar [maximum deviation = 0.005 (3) Å] and is oriented at dihedral angles of 8.23 (8) and 7.29 (9)° with respect to the phenyl and nitro-phenyl rings, respectively. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O inter-actions link the mol-ecules into a two-dimensional network. π-π contacts between rings [centroid-centroid distance = 3.719 (1) Å] may further stabilize the structure.

Related literature

For general background to N-substituted benzamides, see: Beccalli et al. (2005 ▶); Calderone et al. (2006 ▶); Lindgren et al. (2001 ▶); Olsson et al. (2002 ▶); Vega-n class="Chemical">Noverola et al. (1989 ▶); Zhichkin et al. (2007 ▶). For related structures, see: Nissa et al. (2002 ▶, 2004 ▶); Peeters et al. (1986 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C15H12N2O3

M = 268.27

Monoclinic,

a = 5.903 (3) Å

b = 15.050 (9) Å

c = 14.388 (9) Å

β = 95.38 (3)°

V = 1272.6 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.980, T max = 0.984

10408 measured reflections

2886 independent reflections

1994 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.117

S = 1.07

2886 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATOn class="Chemical">N (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030049/hk2746sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030049/hk2746Isup2.hkl

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

C15H12N2O3	F(000) = 560
Mr = 268.27	Dx = 1.400 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10408 reflections
a = 5.903 (3) Å	θ = 3.1–27.4°
b = 15.050 (9) Å	µ = 0.10 mm−1
c = 14.388 (9) Å	T = 173 K
β = 95.38 (3)°	Block, colorless
V = 1272.6 (13) Å3	0.20 × 0.18 × 0.16 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2886 independent reflections
Radiation source: fine-focus sealed tube	1994 reflections with I > 2σ(I)
graphite	Rint = 0.051
φ and ω scans	θmax = 27.4°, θmin = 3.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −7→7
Tmin = 0.980, Tmax = 0.984	k = −18→19
10408 measured reflections	l = −18→18

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.2254P] where P = (Fo2 + 2Fc2)/3
2886 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.20 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
O1	0.73930 (18)	0.43225 (7)	0.92756 (8)	0.0419 (3)
O2	0.2344 (2)	0.02701 (7)	0.81198 (8)	0.0477 (3)
O3	−0.0962 (2)	0.07667 (8)	0.75877 (9)	0.0534 (4)
N1	0.3863 (2)	0.44089 (8)	0.84727 (9)	0.0327 (3)
H1	0.2850	0.4794	0.8233	0.039*
N2	0.1031 (2)	0.08866 (8)	0.79176 (9)	0.0368 (3)
C1	0.7780 (2)	0.71883 (10)	0.93224 (10)	0.0299 (3)
C2	0.9858 (3)	0.75660 (11)	0.96491 (10)	0.0355 (4)
H2	1.1095	0.7191	0.9862	0.043*
C3	1.0150 (3)	0.84803 (11)	0.96685 (11)	0.0416 (4)
H3	1.1580	0.8727	0.9892	0.050*
C4	0.8371 (3)	0.90315 (11)	0.93650 (11)	0.0415 (4)
H4	0.8574	0.9658	0.9375	0.050*
C5	0.6279 (3)	0.86698 (11)	0.90433 (11)	0.0401 (4)
H5	0.5047	0.9048	0.8835	0.048*
C6	0.5991 (3)	0.77560 (10)	0.90259 (10)	0.0346 (4)
H6	0.4553	0.7513	0.8809	0.041*
C7	0.7580 (2)	0.62167 (10)	0.92964 (10)	0.0316 (4)
H7	0.8827	0.5887	0.9584	0.038*
C8	0.5822 (2)	0.57539 (10)	0.89084 (10)	0.0334 (4)
H8	0.4535	0.6061	0.8621	0.040*
C9	0.5825 (2)	0.47700 (10)	0.89143 (10)	0.0316 (4)
C10	0.3266 (2)	0.35165 (10)	0.83539 (10)	0.0282 (3)
C11	0.4746 (2)	0.28151 (10)	0.85797 (10)	0.0316 (4)
H11	0.6261	0.2930	0.8834	0.038*
C12	0.4016 (3)	0.19496 (10)	0.84341 (10)	0.0322 (4)
H12	0.5021	0.1467	0.8586	0.039*
C13	0.1807 (2)	0.17939 (9)	0.80651 (10)	0.0300 (3)
C14	0.0315 (2)	0.24827 (10)	0.78241 (10)	0.0323 (4)
H14	−0.1191	0.2362	0.7562	0.039*
C15	0.1037 (2)	0.33422 (10)	0.79678 (10)	0.0315 (3)
H15	0.0026	0.3821	0.7806	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0340 (6)	0.0328 (6)	0.0563 (7)	0.0019 (5)	−0.0103 (5)	−0.0006 (5)
O2	0.0508 (7)	0.0283 (6)	0.0626 (8)	0.0039 (6)	−0.0020 (6)	0.0050 (5)
O3	0.0390 (7)	0.0386 (7)	0.0794 (9)	−0.0086 (5)	−0.0118 (6)	−0.0074 (6)
N1	0.0305 (7)	0.0242 (7)	0.0418 (7)	0.0007 (5)	−0.0051 (5)	0.0016 (6)
N2	0.0403 (8)	0.0300 (7)	0.0397 (8)	−0.0026 (6)	0.0021 (6)	−0.0015 (6)
C1	0.0325 (8)	0.0302 (8)	0.0269 (7)	−0.0008 (6)	0.0027 (6)	−0.0009 (6)
C2	0.0356 (8)	0.0348 (9)	0.0354 (8)	−0.0007 (7)	−0.0012 (6)	−0.0009 (7)
C3	0.0430 (10)	0.0373 (9)	0.0436 (10)	−0.0102 (8)	−0.0009 (7)	−0.0050 (7)
C4	0.0543 (10)	0.0278 (9)	0.0426 (10)	−0.0049 (8)	0.0057 (8)	−0.0017 (7)
C5	0.0453 (10)	0.0328 (9)	0.0420 (9)	0.0059 (8)	0.0024 (7)	0.0025 (7)
C6	0.0328 (8)	0.0346 (9)	0.0358 (8)	−0.0008 (7)	0.0009 (6)	−0.0010 (7)
C7	0.0330 (8)	0.0311 (8)	0.0307 (8)	0.0010 (7)	0.0027 (6)	0.0005 (6)
C8	0.0318 (8)	0.0306 (8)	0.0370 (8)	−0.0003 (7)	−0.0003 (6)	0.0021 (7)
C9	0.0307 (8)	0.0303 (8)	0.0337 (8)	−0.0026 (7)	0.0016 (6)	0.0003 (6)
C10	0.0298 (8)	0.0272 (8)	0.0275 (7)	0.0004 (6)	0.0019 (6)	−0.0002 (6)
C11	0.0282 (8)	0.0311 (8)	0.0344 (8)	0.0008 (6)	−0.0029 (6)	−0.0004 (6)
C12	0.0330 (8)	0.0298 (8)	0.0332 (8)	0.0036 (7)	−0.0009 (6)	0.0001 (6)
C13	0.0329 (8)	0.0248 (7)	0.0322 (8)	−0.0016 (6)	0.0027 (6)	−0.0007 (6)
C14	0.0271 (7)	0.0332 (8)	0.0363 (8)	−0.0016 (7)	0.0013 (6)	−0.0020 (7)
C15	0.0283 (7)	0.0314 (8)	0.0343 (8)	0.0033 (6)	0.0010 (6)	0.0016 (7)

O1—C9	1.2207 (18)	C5—H5	0.9500
O2—N2	1.2264 (17)	C6—H6	0.9500
O3—N2	1.2397 (17)	C7—C8	1.329 (2)
N1—C9	1.3790 (19)	C7—H7	0.9500
N1—C10	1.395 (2)	C8—C9	1.481 (2)
N1—H1	0.8800	C8—H8	0.9500
N2—C13	1.450 (2)	C10—C11	1.389 (2)
C1—C2	1.393 (2)	C10—C15	1.404 (2)
C1—C6	1.394 (2)	C11—C12	1.382 (2)
C1—C7	1.467 (2)	C11—H11	0.9500
C2—C3	1.387 (2)	C12—C13	1.381 (2)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.377 (2)	C13—C14	1.383 (2)
C3—H3	0.9500	C14—C15	1.372 (2)
C4—C5	1.389 (2)	C14—H14	0.9500
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.386 (2)
C9—N1—C10	128.87 (13)	C1—C7—H7	116.9
C9—N1—H1	115.6	C7—C8—C9	121.43 (14)
C10—N1—H1	115.6	C7—C8—H8	119.3
O2—N2—O3	122.46 (13)	C9—C8—H8	119.3
O2—N2—C13	119.59 (13)	O1—C9—N1	123.31 (14)
O3—N2—C13	117.95 (13)	O1—C9—C8	123.67 (14)
C2—C1—C6	118.10 (14)	N1—C9—C8	113.01 (13)
C2—C1—C7	118.78 (14)	C11—C10—N1	123.82 (13)
C6—C1—C7	123.12 (13)	C11—C10—C15	119.74 (14)
C3—C2—C1	121.03 (15)	N1—C10—C15	116.44 (13)
C3—C2—H2	119.5	C12—C11—C10	120.02 (14)
C1—C2—H2	119.5	C12—C11—H11	120.0
C4—C3—C2	120.12 (15)	C10—C11—H11	120.0
C4—C3—H3	119.9	C13—C12—C11	119.22 (14)
C2—C3—H3	119.9	C13—C12—H12	120.4
C3—C4—C5	119.84 (15)	C11—C12—H12	120.4
C3—C4—H4	120.1	C12—C13—C14	121.69 (14)
C5—C4—H4	120.1	C12—C13—N2	119.36 (13)
C6—C5—C4	119.92 (15)	C14—C13—N2	118.95 (14)
C6—C5—H5	120.0	C15—C14—C13	119.18 (14)
C4—C5—H5	120.0	C15—C14—H14	120.4
C5—C6—C1	120.97 (15)	C13—C14—H14	120.4
C5—C6—H6	119.5	C14—C15—C10	120.14 (14)
C1—C6—H6	119.5	C14—C15—H15	119.9
C8—C7—C1	126.22 (14)	C10—C15—H15	119.9
C8—C7—H7	116.9
C6—C1—C2—C3	−0.8 (2)	C9—N1—C10—C15	172.82 (14)
C7—C1—C2—C3	178.57 (14)	N1—C10—C11—C12	−179.62 (14)
C1—C2—C3—C4	0.2 (2)	C15—C10—C11—C12	−0.7 (2)
C2—C3—C4—C5	0.3 (2)	C10—C11—C12—C13	−0.1 (2)
C3—C4—C5—C6	−0.2 (2)	C11—C12—C13—C14	1.0 (2)
C4—C5—C6—C1	−0.4 (2)	C11—C12—C13—N2	−179.58 (14)
C2—C1—C6—C5	0.9 (2)	O2—N2—C13—C12	−0.2 (2)
C7—C1—C6—C5	−178.44 (14)	O3—N2—C13—C12	179.82 (14)
C2—C1—C7—C8	−171.67 (14)	O2—N2—C13—C14	179.28 (14)
C6—C1—C7—C8	7.6 (2)	O3—N2—C13—C14	−0.7 (2)
C1—C7—C8—C9	179.17 (14)	C12—C13—C14—C15	−1.0 (2)
C10—N1—C9—O1	0.5 (2)	N2—C13—C14—C15	179.59 (13)
C10—N1—C9—C8	−179.20 (14)	C13—C14—C15—C10	0.1 (2)
C7—C8—C9—O1	0.8 (2)	C11—C10—C15—C14	0.8 (2)
C7—C8—C9—N1	−179.53 (14)	N1—C10—C15—C14	179.72 (13)
C9—N1—C10—C11	−8.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.88	2.13	2.991 (2)	166
C5—H5···O2ii	0.95	2.58	3.519 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.88	2.13	2.991 (2)	166
C5—H5⋯O2ii	0.95	2.58	3.519 (2)	168

Symmetry codes: (i) ; (ii) .