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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o521.
Published online 2008 January 25. doi:  10.1107/S1600536808002298
PMCID: PMC2960181

N-(2-Methyl­phen­yl)-2-nitro­benzamide

Abstract

In the title compound, C14H12N2O3, the dihedral angle between the two aromatic rings is 41.48 (5)°. The nitro group is twisted by 24.7 (3)° out of the plane of the aromatic ring to which it is attached. The mol­ecules are connected by N—H(...)O hydrogen bonds into chains running along the a axis.

Related literature

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

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Object name is e-64-0o521-scheme1.jpg

Experimental

Crystal data

  • C14H12N2O3
  • M r = 256.26
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o521-efi1.jpg
  • a = 7.8063 (10) Å
  • b = 12.2856 (11) Å
  • c = 13.1353 (13) Å
  • V = 1259.7 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 273 (2) K
  • 0.35 × 0.14 × 0.13 mm

Data collection

  • Stoe IPDSII two-circle diffractometer
  • Absorption correction: none
  • 4741 measured reflections
  • 1364 independent reflections
  • 1243 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.077
  • S = 1.02
  • 1364 reflections
  • 178 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 [triangle]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002298/at2536sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002298/at2536Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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 towards benzothiadiazin-4-ones (Makino et al., 2003), quinazoline-2,4-diones (Makino et al., 2001) and benzodiazepine-2,5-diones (Ho et al., 2002) and 110 kinase inhibitors 2,3-disubstituted 3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficacy as centroid elements of ligands that bind to a wide variety of receptor types. Thus benzanilides containing aminoalkyl groups originally designed as a peptidomimetic, have 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 benzanilide are vascular endothelial growth factor receptor and tyrosine kinase inhibitor (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 are in the usual ranges. The dihedral angle between the two aromatic rings is 41.48 (5)°. The nitro group is twisted by 24.7 (3)° out of the plane of the aromatic ring to which it is attached. The molecules crystallize in chains running along the a axis. The molecules in a chain are connected by N—H···O hydrogen bonds.

Refinement

Due to the absence of any anomalous scatterer, Friedel pairs were merged prior to refinement and the absolute structure was arbitrarily set. All H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [Uiso(H) = 1.2or 1.5 Ueq(C)] using a riding model with C—H = 0.95 Å. The amino H atom was freely refined.

Figures

Fig. 1.
Molecular structure of title compound with displacement ellipsoids at the 50% probability level.

Crystal data

C14H12N2O3F000 = 536
Mr = 256.26Dx = 1.351 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3989 reflections
a = 7.8063 (10) Åθ = 3.6–25.7º
b = 12.2856 (11) ŵ = 0.10 mm1
c = 13.1353 (13) ÅT = 273 (2) K
V = 1259.7 (2) Å3Needle, light brown
Z = 40.35 × 0.14 × 0.13 mm

Data collection

Stoe IPDSII two-circle diffractometer1243 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Monochromator: graphiteθmax = 25.5º
T = 273(2) Kθmin = 3.5º
ω scansh = −8→9
Absorption correction: nonek = −14→12
4741 measured reflectionsl = −15→15
1364 independent reflections

Refinement

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)] = 0.031  w = 1/[σ2(Fo2) + (0.0533P)2 + 0.0696P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.13 e Å3
1364 reflectionsΔρmin = −0.14 e Å3
178 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (3)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
N10.6342 (2)0.68690 (13)0.54004 (11)0.0240 (4)
H10.553 (3)0.726 (2)0.5746 (17)0.040 (7)*
C10.7172 (2)0.73801 (15)0.46407 (13)0.0227 (4)
O10.82960 (19)0.69697 (10)0.41024 (10)0.0277 (3)
N20.5272 (2)0.82075 (14)0.28700 (12)0.0302 (4)
O20.5146 (3)0.85091 (14)0.19817 (11)0.0495 (5)
O30.4810 (2)0.73064 (12)0.31740 (11)0.0388 (4)
C110.6745 (2)0.85748 (16)0.45063 (13)0.0239 (4)
C120.5996 (3)0.89811 (16)0.36185 (14)0.0251 (4)
C130.5832 (3)1.00790 (17)0.34180 (16)0.0341 (5)
H130.53221.03170.28180.041*
C140.6439 (3)1.08187 (18)0.41256 (18)0.0405 (5)
H140.63401.15620.40040.049*
C150.7190 (3)1.04525 (17)0.50114 (18)0.0383 (5)
H150.75981.09520.54850.046*
C160.7347 (3)0.93358 (17)0.52071 (16)0.0321 (5)
H160.78560.91010.58080.038*
C210.6503 (3)0.57434 (16)0.56687 (14)0.0246 (4)
C220.6130 (3)0.54470 (17)0.66744 (14)0.0284 (4)
C230.6223 (3)0.43408 (19)0.69291 (17)0.0384 (5)
H230.59680.41240.75900.046*
C240.6687 (4)0.35605 (18)0.62128 (18)0.0417 (6)
H240.67560.28310.63990.050*
C250.7045 (3)0.38710 (17)0.52281 (17)0.0392 (5)
H250.73530.33490.47490.047*
C260.6949 (3)0.49615 (17)0.49469 (15)0.0316 (5)
H260.71810.51680.42800.038*
C270.5619 (3)0.6283 (2)0.74710 (14)0.0365 (5)
H27A0.64710.68460.75010.055*
H27B0.55310.59350.81240.055*
H27C0.45330.65950.72920.055*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0313 (9)0.0204 (8)0.0201 (8)0.0029 (7)0.0025 (7)0.0010 (6)
C10.0261 (10)0.0223 (9)0.0198 (8)−0.0011 (8)−0.0039 (7)−0.0026 (7)
O10.0326 (8)0.0226 (7)0.0278 (7)−0.0013 (6)0.0060 (6)−0.0034 (5)
N20.0338 (9)0.0316 (10)0.0251 (8)0.0001 (8)−0.0025 (7)0.0009 (7)
O20.0736 (13)0.0524 (10)0.0226 (7)−0.0003 (10)−0.0107 (8)0.0060 (7)
O30.0504 (10)0.0302 (7)0.0358 (7)−0.0138 (7)−0.0059 (7)−0.0001 (6)
C110.0259 (10)0.0206 (9)0.0252 (9)0.0001 (8)0.0029 (8)−0.0013 (7)
C120.0259 (10)0.0244 (10)0.0250 (9)−0.0034 (8)0.0018 (8)0.0009 (7)
C130.0388 (12)0.0262 (11)0.0373 (10)0.0009 (9)0.0015 (10)0.0096 (9)
C140.0439 (13)0.0210 (10)0.0565 (14)0.0021 (10)−0.0018 (11)0.0034 (10)
C150.0425 (13)0.0233 (10)0.0492 (13)−0.0015 (10)−0.0036 (11)−0.0101 (9)
C160.0377 (12)0.0271 (10)0.0314 (10)0.0034 (9)−0.0054 (9)−0.0050 (8)
C210.0274 (10)0.0224 (9)0.0242 (8)0.0002 (8)−0.0025 (8)0.0036 (7)
C220.0311 (10)0.0300 (10)0.0241 (9)0.0019 (9)−0.0024 (8)0.0053 (8)
C230.0465 (13)0.0357 (12)0.0330 (10)0.0005 (10)−0.0003 (10)0.0134 (9)
C240.0532 (14)0.0230 (10)0.0490 (12)0.0001 (11)0.0022 (12)0.0116 (10)
C250.0522 (14)0.0231 (10)0.0422 (11)−0.0016 (10)0.0020 (11)−0.0017 (9)
C260.0439 (13)0.0230 (9)0.0278 (10)−0.0016 (9)0.0016 (9)0.0020 (8)
C270.0451 (13)0.0436 (13)0.0209 (9)0.0077 (11)0.0032 (9)0.0031 (9)

Geometric parameters (Å, °)

N1—C11.345 (2)C15—H150.9300
N1—C211.433 (2)C16—H160.9300
N1—H10.92 (3)C21—C261.394 (3)
C1—O11.234 (2)C21—C221.401 (3)
C1—C111.515 (3)C22—C231.401 (3)
N2—O21.228 (2)C22—C271.519 (3)
N2—O31.231 (2)C23—C241.391 (3)
N2—C121.480 (3)C23—H230.9300
C11—C161.393 (3)C24—C251.377 (3)
C11—C121.397 (3)C24—H240.9300
C12—C131.380 (3)C25—C261.392 (3)
C13—C141.384 (3)C25—H250.9300
C13—H130.9300C26—H260.9300
C14—C151.379 (3)C27—H27A0.9600
C14—H140.9300C27—H27B0.9600
C15—C161.401 (3)C27—H27C0.9600
C1—N1—C21126.20 (17)C15—C16—H16119.8
C1—N1—H1117.5 (15)C26—C21—C22120.94 (18)
C21—N1—H1116.1 (16)C26—C21—N1121.32 (16)
O1—C1—N1125.21 (18)C22—C21—N1117.68 (17)
O1—C1—C11119.02 (17)C21—C22—C23117.80 (19)
N1—C1—C11115.63 (16)C21—C22—C27121.89 (18)
O2—N2—O3123.79 (18)C23—C22—C27120.30 (18)
O2—N2—C12117.91 (17)C24—C23—C22121.35 (19)
O3—N2—C12118.30 (16)C24—C23—H23119.3
C16—C11—C12116.93 (18)C22—C23—H23119.3
C16—C11—C1119.92 (16)C25—C24—C23119.8 (2)
C12—C11—C1122.37 (16)C25—C24—H24120.1
C13—C12—C11123.19 (18)C23—C24—H24120.1
C13—C12—N2117.73 (18)C24—C25—C26120.3 (2)
C11—C12—N2119.03 (17)C24—C25—H25119.8
C12—C13—C14118.8 (2)C26—C25—H25119.8
C12—C13—H13120.6C25—C26—C21119.76 (19)
C14—C13—H13120.6C25—C26—H26120.1
C15—C14—C13119.9 (2)C21—C26—H26120.1
C15—C14—H14120.1C22—C27—H27A109.5
C13—C14—H14120.1C22—C27—H27B109.5
C14—C15—C16120.8 (2)H27A—C27—H27B109.5
C14—C15—H15119.6C22—C27—H27C109.5
C16—C15—H15119.6H27A—C27—H27C109.5
C11—C16—C15120.4 (2)H27B—C27—H27C109.5
C11—C16—H16119.8
C21—N1—C1—O1−5.4 (3)C13—C14—C15—C16−0.1 (4)
C21—N1—C1—C11178.96 (17)C12—C11—C16—C150.0 (3)
O1—C1—C11—C16−103.0 (2)C1—C11—C16—C15170.1 (2)
N1—C1—C11—C1672.9 (2)C14—C15—C16—C110.1 (4)
O1—C1—C11—C1266.5 (3)C1—N1—C21—C26−27.7 (3)
N1—C1—C11—C12−117.6 (2)C1—N1—C21—C22154.78 (19)
C16—C11—C12—C13−0.2 (3)C26—C21—C22—C230.1 (3)
C1—C11—C12—C13−170.0 (2)N1—C21—C22—C23177.60 (19)
C16—C11—C12—N2−177.46 (18)C26—C21—C22—C27−179.2 (2)
C1—C11—C12—N212.7 (3)N1—C21—C22—C27−1.7 (3)
O2—N2—C12—C1326.3 (3)C21—C22—C23—C240.7 (3)
O3—N2—C12—C13−152.8 (2)C27—C22—C23—C24−180.0 (2)
O2—N2—C12—C11−156.3 (2)C22—C23—C24—C25−0.8 (4)
O3—N2—C12—C1124.7 (3)C23—C24—C25—C260.2 (4)
C11—C12—C13—C140.2 (3)C24—C25—C26—C210.6 (4)
N2—C12—C13—C14177.49 (19)C22—C21—C26—C25−0.7 (3)
C12—C13—C14—C150.0 (3)N1—C21—C26—C25−178.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.92 (3)1.99 (3)2.849 (2)155 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2536).

References

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  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Stoe & Cie (2001). X-AREA Stoe & Cie, Darmstadt, Germany.
  • Zhichkin, P., Kesicki, E., Treiberg, J., Bourdon, L. M., Ronsheim, M., Ooi, H. C., White, S., Judkins, A. & Fairfax, D. (2007). Org. Lett.9, 1415–1418. [PubMed]

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