N-(4-Nitro­phen­yl)cinnamamide

Saeed, A.; Khera, R.A.; Shahid, M.; Parvez, M.

doi:10.1107/S1600536809030049

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2068

doi:10.1107/S1600536809030049

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N-(4-Nitrophenyl)cinnamamide

Aamer Saeed,^a Rasheed Ahmad Khera,^a Muhammad Shahid ^b and Masood Parvez ^c ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bHamdard Institute of Pharmaceutical Sciences, Hamdard University, Islamabad Campus, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 22 July 2009; accepted 29 July 2009; online 8 August 2009)

In the molecule of the title compound, C₁₅H₁₂N₂O₃, the dihedral angle between the rings is 3.04 (8)°. The central NOC₃ 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 nitrophenyl rings, respectively. In the crystal structure, intermolecular N—H⋯O and C—H⋯O interactions link the molecules 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-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_r = 268.27
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.117
S = 1.07
2886 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y+1, z.

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 (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Supporting information

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

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

checkCIF report

Comment top

N-substituted benzamides, e.g., declopramideare, are well known anticancer compounds and the mechanism of benzamide-induced apoptosis has been studied, (Olsson et al., 2002). N-substituted benzamides inhibit the activity of nuclear factor-B and nuclear factor of activated T cells (Lindgren et al., 2001). Various N-substituted benzamides exhibit potent antiemetic activity (Vega-Noverola et al., 1989), while heterocyclic benzanilide are potassium channel activators (Calderone et al., 2006). N-Alkylated 2-nitrobenzamides are intermediates in the synthesis of dibenzo[b,e][1,4]diazepines (Zhichkin et al., 2007) and N-Acyl-2-nitrobenzamides are precursors of 2,3-disubstitued 3H-quinazoline-4-ones (Beccalli et al., 2005). As part of our work on the structure of benzanilides and related compounds, we report herein the crystal structure of the title compound.

A search of the Cambridge Crystallographic Database (CSD version 5.30; Allen, 2002) for a fragment containing the title compound without NO₂ group revealed only four entries containg the basic skeleton of the title compound with refcodes: DIPHUF (Peeters et al., 1986), EHATUC and EHAVAK (Nissa et al., 2002) and FALQAL (Nissa et al., 2004).

In the molecule of the title compound (Fig. 1), rings A (C1-C6) and B (C10-C15) are, of course, planar and they are oriented at a dihedral angle of A/B = 3.04 (8)°. The (O1/N1/C7-C9) moiety is planar with a maximum deviation of -0.005 (3) Å for atom C8 and it is oriented with respect to rings A and B at dihedral angles of 8.23 (8) and 7.29 (9) °, respectively.

In the crystal structure, intermolecular N-H···O and C-H···O interactions (Table 1) link the molecules into a two dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the phenyl rings, Cg1—Cg2ⁱ [symmetry code: (i) 1 - x, y - 1/2, 1/2 - z, where Cg1 and Cg2 are centroids of the rings A (C1-C6) and B (C10-C15), respectively] may further stabilize the structure, with centroid-centroid distance of 3.719 (1) Å.

Related literature top

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-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 top

For the preparation of the title compound, cinnamic acid was converted into cinnamoyl chloride using the standard procedure. A stirred solution of cinnamoyl chloride (5.4 mmol) in CHCl₃ was treated with p-nitroaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 4 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq 1.0 M HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue in MeOH afforded the title compound (yield; 81%) as colorless crystals: Anal. calcd. for C₁₅H₁₂N₂O₃: C, 67.16; H, 4.51; N, 10.44; found: C, 67.21; H, 4.59; N, 10.41.

Computing details top

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 (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.

N-(4-Nitrophenyl)cinnamamide top

Crystal data top

C₁₅H₁₂N₂O₃	F(000) = 560
M_r = 268.27	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0545P)² + 0.2254P] where P = (F_o² + 2F_c²)/3
2886 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₂N₂O₃	V = 1272.6 (13) Å³
M_r = 268.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.903 (3) Å	µ = 0.10 mm⁻¹
b = 15.050 (9) Å	T = 173 K
c = 14.388 (9) Å	0.20 × 0.18 × 0.16 mm
β = 95.38 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2886 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	1994 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.984	R_int = 0.051
10408 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.07	Δρ_max = 0.17 e Å⁻³
2886 reflections	Δρ_min = −0.20 e Å⁻³
181 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+3/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O₃
M_r	268.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	5.903 (3), 15.050 (9), 14.388 (9)
β (°)	95.38 (3)
V (Å³)	1272.6 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.980, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	10408, 2886, 1994
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.117, 1.07
No. of reflections	2886
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.88	2.13	2.991 (2)	166.4
C5—H5···O2ⁱⁱ	0.95	2.58	3.519 (2)	168.0

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x, y+1, z.

Acknowledgements

AS gratefully acknowledges a research grant from Quaid-i-Azam University Islamabad under the URF program.

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