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Acta Cryst. (2008). E64, o603    [ doi:10.1107/S1600536808002626 ]

N-(2-Methoxyphenyl)-2-nitrobenzamide

A. Saeed, S. Hussain and M. Bolte

Abstract top

Geometric parameters of the title compound, C14H12N2O4, are in the usual ranges. The dihedral angle between the two aromatic rings is 28.9 (1)°. The nitro group is twisted by 40.2 (1)° out of the plane of the aromatic ring to which it is attached. The crystal structure is stabilized by an N-H...O hydrogen bond.

Comment top

The benzanilide core is present in compounds with such a wide range of biological activities that it has been called a privileged structure. Benzanilides serve as intermediates to benzothiadiazin-4-ones (Makino et al., 2003), quinazoline-2,4-diones (Makino et al., 2001), benzodiazepine-2,5-diones (Ho et al., 2002) and 2,3-disubstituted 3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficacy as central elements of ligands that bind to a wide variety of receptor types. Thus a benzanilide containing aminoalkyl groups originally designed as a peptidomimetic has been incorporated in an Arg-Gly-Asp cyclic peptide yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib is an ATP-site binding kinase inhibitor and platelet-derived growth factor receptor kinases (Capdeville et al., 2002). Pyridylmethyl containing benzanilides are vascular endothelial growth factor receptors and tyrosine kinase inhibitors (Manley et al., 2002). Furthermore, benzamides have been reported to have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999)

Geometric parameters of the title compound, C14H12N2O4, are in the usual ranges. The dihedral angle between the two aromatic rings is 28.9 (1)°. The nitrogroup is twisted by 40.2 (1)° out of the plane of the phenyl ring to which it is attached. The crystal structure is stabilized by an N—H···O hydrogen bond.

Related literature top

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

Experimental top

A mixture of 2-methoxyaniline (10.0 g, 65.7 mmol), 2-nitrobenzoyl chloride (10 ml, 86.9 mmol), and pyridine (20 ml) was left at 25 °C for 15 h. Water (100 ml) was then added, and the resulting precipitate was collected. Recrystallization of the precipitate from benzene gave 12.6 g (75%) of the title compound as yellow blocks: mp 95–96 °C 1H NMR (CDCl3) δ 7.23–8.30 (m, 8H, Ar—Hs), 11.36 (br s, 1H, NH).

Refinement top

In the absence of anomalous scatterers, Friedel pairs had been merged and the absolute structure was arbitrarily assigned. All H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C) or U(H) = 1.5 Ueq(Cmethyl)] using a riding model with C—H = 0.95Å or C—H = 0.98Å for aromatic and methyl C, respectively. The methyl group was allowed to rotate, but not to tip. The amino H atom was freely refined.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound.
N-(2-Methoxyphenyl)-2-nitrobenzamide top
Crystal data top
C14H12N2O4Dx = 1.444 Mg m−3
Mr = 272.26Mo Kα radiation
λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 7856 reflections
a = 7.6467 (11) Åθ = 3.8–25.6º
b = 9.9272 (8) ŵ = 0.11 mm−1
c = 16.5032 (14) ÅT = 173 (2) K
V = 1252.8 (2) Å3Block, light yellow
Z = 40.37 × 0.33 × 0.21 mm
F000 = 568
Data collection top
Stoe IPDSII two-circle
diffractometer		1275 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Monochromator: graphiteθmax = 25.6º
T = 173(2) Kθmin = 3.6º
ω scansh = −7→9
Absorption correction: nonek = −12→12
8342 measured reflectionsl = −20→18
1368 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044  w = 1/[σ2(Fo2) + (0.0824P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.28 e Å−3
1368 reflectionsΔρmin = −0.21 e Å−3
187 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.052 (7)
Secondary atom site location: difference Fourier map
Crystal data top
C14H12N2O4V = 1252.8 (2) Å3
Mr = 272.26Z = 4
Orthorhombic, P212121Mo Kα
a = 7.6467 (11) ŵ = 0.11 mm−1
b = 9.9272 (8) ÅT = 173 (2) K
c = 16.5032 (14) Å0.37 × 0.33 × 0.21 mm
Data collection top
Stoe IPDSII two-circle
diffractometer		1368 independent reflections
Absorption correction: none1275 reflections with I > 2σ(I)
8342 measured reflectionsRint = 0.042
Refinement top
R[F2 > 2σ(F2)] = 0.044Δρmax = 0.28 e Å−3
wR(F2) = 0.110Δρmin = −0.21 e Å−3
S = 1.05Absolute structure: ?
1368 reflectionsFlack parameter: ?
187 parametersRogers parameter: ?
H atoms treated by a mixture of
independent and constrained refinement
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
xyzUiso*/Ueq
C10.7040 (3)0.4189 (2)0.58905 (15)0.0271 (5)
N10.6935 (3)0.46807 (19)0.51339 (14)0.0287 (5)
H10.618 (5)0.449 (3)0.4799 (19)0.040 (9)*
N20.7600 (3)0.14453 (18)0.64422 (13)0.0299 (5)
O10.8235 (3)0.44489 (17)0.63779 (11)0.0370 (5)
O20.8450 (3)0.16188 (18)0.58190 (13)0.0410 (5)
O30.8114 (3)0.07915 (18)0.70333 (13)0.0419 (5)
O40.5752 (2)0.62521 (16)0.39737 (11)0.0305 (5)
C110.5537 (3)0.3307 (2)0.61508 (14)0.0263 (5)
C120.5833 (3)0.2030 (2)0.64870 (16)0.0264 (5)
C130.4498 (4)0.1261 (2)0.68256 (15)0.0307 (6)
H130.47440.04040.70550.037*
C140.2795 (4)0.1764 (2)0.68236 (17)0.0338 (6)
H140.18690.12480.70490.041*
C150.2456 (4)0.3028 (3)0.64891 (17)0.0360 (6)
H150.12940.33680.64830.043*
C160.3821 (4)0.3800 (2)0.61615 (17)0.0324 (6)
H160.35790.46670.59450.039*
C210.8150 (3)0.5560 (2)0.47494 (14)0.0260 (5)
C220.7505 (3)0.6385 (2)0.41263 (15)0.0267 (5)
C230.8635 (4)0.7254 (2)0.37131 (16)0.0293 (6)
H230.81990.78250.32970.035*
C241.0410 (4)0.7277 (2)0.39163 (16)0.0314 (6)
H241.11770.78720.36380.038*
C251.1068 (4)0.6440 (2)0.45211 (17)0.0323 (6)
H251.22800.64520.46490.039*
C260.9933 (4)0.5579 (2)0.49399 (15)0.0299 (5)
H261.03740.50070.53540.036*
C270.5074 (4)0.6982 (2)0.32917 (16)0.0323 (6)
H27A0.52110.79510.33850.048*
H27B0.38310.67690.32220.048*
H27C0.57170.67240.28020.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0227 (13)0.0256 (10)0.0331 (13)0.0022 (9)−0.0009 (10)−0.0013 (9)
N10.0195 (11)0.0312 (10)0.0354 (12)−0.0040 (8)−0.0015 (10)0.0024 (8)
N20.0261 (12)0.0246 (9)0.0390 (12)0.0014 (9)−0.0020 (9)−0.0034 (8)
O10.0324 (11)0.0415 (9)0.0372 (10)−0.0095 (9)−0.0085 (8)0.0057 (8)
O20.0308 (11)0.0429 (9)0.0491 (11)0.0067 (8)0.0110 (9)0.0029 (9)
O30.0413 (12)0.0373 (8)0.0470 (12)0.0104 (9)−0.0093 (9)0.0037 (8)
O40.0209 (9)0.0330 (8)0.0374 (10)−0.0019 (7)−0.0012 (8)0.0062 (7)
C110.0217 (12)0.0282 (11)0.0289 (12)0.0003 (10)−0.0005 (11)0.0009 (9)
C120.0208 (14)0.0269 (10)0.0315 (12)−0.0008 (9)0.0007 (10)−0.0038 (9)
C130.0312 (15)0.0271 (10)0.0338 (13)−0.0040 (10)0.0025 (12)−0.0029 (9)
C140.0268 (15)0.0368 (12)0.0377 (14)−0.0069 (11)0.0047 (12)−0.0027 (10)
C150.0216 (14)0.0457 (13)0.0408 (15)0.0011 (11)0.0024 (12)−0.0023 (11)
C160.0255 (14)0.0355 (12)0.0362 (13)0.0055 (10)0.0001 (12)0.0043 (10)
C210.0216 (12)0.0247 (10)0.0315 (12)−0.0026 (10)0.0041 (10)0.0000 (9)
C220.0210 (12)0.0261 (10)0.0328 (12)−0.0010 (9)0.0016 (10)−0.0011 (9)
C230.0270 (14)0.0264 (10)0.0345 (13)−0.0007 (10)0.0036 (11)0.0005 (9)
C240.0247 (14)0.0304 (11)0.0390 (14)−0.0047 (10)0.0044 (12)−0.0004 (10)
C250.0225 (13)0.0345 (12)0.0398 (13)−0.0043 (11)−0.0005 (11)−0.0034 (10)
C260.0243 (13)0.0328 (12)0.0326 (12)0.0005 (11)−0.0010 (10)−0.0008 (9)
C270.0240 (14)0.0362 (12)0.0367 (14)0.0010 (10)−0.0036 (11)0.0074 (9)
Geometric parameters (Å, °) top
C1—O11.244 (3)C15—C161.404 (4)
C1—N11.343 (3)C15—H150.9500
C1—C111.508 (3)C16—H160.9500
N1—C211.424 (3)C21—C261.399 (4)
N1—H10.82 (4)C21—C221.404 (3)
N2—O21.229 (3)C22—C231.399 (3)
N2—O31.236 (3)C23—C241.399 (4)
N2—C121.473 (3)C23—H230.9500
O4—C221.371 (3)C24—C251.393 (4)
O4—C271.435 (3)C24—H240.9500
C11—C161.400 (4)C25—C261.401 (4)
C11—C121.402 (3)C25—H250.9500
C12—C131.392 (4)C26—H260.9500
C13—C141.395 (4)C27—H27A0.9800
C13—H130.9500C27—H27B0.9800
C14—C151.395 (4)C27—H27C0.9800
C14—H140.9500
O1—C1—N1124.7 (2)C11—C16—H16119.6
O1—C1—C11119.7 (2)C15—C16—H16119.6
N1—C1—C11115.5 (2)C26—C21—C22119.9 (2)
C1—N1—C21126.7 (2)C26—C21—N1122.9 (2)
C1—N1—H1126 (2)C22—C21—N1117.1 (2)
C21—N1—H1107 (2)O4—C22—C23125.0 (2)
O2—N2—O3124.5 (2)O4—C22—C21115.0 (2)
O2—N2—C12118.2 (2)C23—C22—C21120.0 (2)
O3—N2—C12117.3 (2)C22—C23—C24119.5 (2)
C22—O4—C27116.69 (19)C22—C23—H23120.2
C16—C11—C12117.5 (2)C24—C23—H23120.2
C16—C11—C1121.0 (2)C25—C24—C23120.8 (2)
C12—C11—C1121.0 (2)C25—C24—H24119.6
C13—C12—C11122.5 (2)C23—C24—H24119.6
C13—C12—N2118.5 (2)C24—C25—C26119.6 (3)
C11—C12—N2119.0 (2)C24—C25—H25120.2
C12—C13—C14119.1 (2)C26—C25—H25120.2
C12—C13—H13120.4C21—C26—C25120.1 (2)
C14—C13—H13120.4C21—C26—H26120.0
C13—C14—C15119.8 (2)C25—C26—H26120.0
C13—C14—H14120.1O4—C27—H27A109.5
C15—C14—H14120.1O4—C27—H27B109.5
C14—C15—C16120.3 (3)H27A—C27—H27B109.5
C14—C15—H15119.8O4—C27—H27C109.5
C16—C15—H15119.8H27A—C27—H27C109.5
C11—C16—C15120.7 (2)H27B—C27—H27C109.5
O1—C1—N1—C210.8 (4)C12—C11—C16—C15−0.8 (4)
C11—C1—N1—C21178.3 (2)C1—C11—C16—C15−172.8 (2)
O1—C1—C11—C16118.2 (3)C14—C15—C16—C111.2 (4)
N1—C1—C11—C16−59.5 (3)C1—N1—C21—C2629.1 (4)
O1—C1—C11—C12−53.6 (3)C1—N1—C21—C22−154.1 (2)
N1—C1—C11—C12128.8 (2)C27—O4—C22—C235.6 (3)
C16—C11—C12—C13−0.2 (4)C27—O4—C22—C21−174.3 (2)
C1—C11—C12—C13171.8 (2)C26—C21—C22—O4177.9 (2)
C16—C11—C12—N2176.4 (2)N1—C21—C22—O41.0 (3)
C1—C11—C12—N2−11.6 (3)C26—C21—C22—C23−2.0 (3)
O2—N2—C12—C13138.0 (3)N1—C21—C22—C23−178.8 (2)
O3—N2—C12—C13−40.8 (3)O4—C22—C23—C24−178.8 (2)
O2—N2—C12—C11−38.8 (3)C21—C22—C23—C241.1 (4)
O3—N2—C12—C11142.4 (2)C22—C23—C24—C250.4 (4)
C11—C12—C13—C140.8 (4)C23—C24—C25—C26−1.0 (4)
N2—C12—C13—C14−175.8 (2)C22—C21—C26—C251.3 (4)
C12—C13—C14—C15−0.4 (4)N1—C21—C26—C25178.0 (2)
C13—C14—C15—C16−0.6 (4)C24—C25—C26—C210.1 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.82 (4)2.57 (4)3.352 (3)159 (3)
Symmetry codes: (i) x−1/2, −y+1/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.82 (4)2.57 (4)3.352 (3)159 (3)
Symmetry codes: (i) x−1/2, −y+1/2, −z+1.
Acknowledgements top

AS gratefully acknowledges a research grant from Quaid-i-Azam University, Islamabad.

references
References top

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