N-(2-Methyl­phen­yl)-2-nitro­benzamide

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.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.078
• Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.66

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.52
           From the CIF: _reflns_number_total               1364
           Count of symmetry unique reflns         1371
           Completeness (_total/calc)             99.49%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. 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.

Related literature

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

S2. 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 [U_iso(H) = 1.2or 1.5 U_eq(C)] using a riding model with C—H = 0.95 Å. The amino H atom was freely refined.

Computing details

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

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

N-(2-Methylphenyl)-2-nitrobenzamide

Crystal data

C14H12N2O3	F(000) = 536
Mr = 256.26	Dx = 1.351 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3989 reflections
a = 7.8063 (10) Å	θ = 3.6–25.7°
b = 12.2856 (11) Å	µ = 0.10 mm^−1
c = 13.1353 (13) Å	T = 273 K
V = 1259.7 (2) Å^3	Needle, light brown
Z = 4	0.35 × 0.14 × 0.13 mm

Data collection

Stoe IPDSII two-circle diffractometer	1243 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.5°, θmin = 3.5°
ω scans	h = −8→9
4741 measured reflections	k = −14→12
1364 independent reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0533P)^2 + 0.0696P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
1364 reflections	Δρmax = 0.13 e Å^−3
178 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (3)

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.6342 (2)	0.68690 (13)	0.54004 (11)	0.0240 (4)
H1	0.553 (3)	0.726 (2)	0.5746 (17)	0.040 (7)*
C1	0.7172 (2)	0.73801 (15)	0.46407 (13)	0.0227 (4)
O1	0.82960 (19)	0.69697 (10)	0.41024 (10)	0.0277 (3)
N2	0.5272 (2)	0.82075 (14)	0.28700 (12)	0.0302 (4)
O2	0.5146 (3)	0.85091 (14)	0.19817 (11)	0.0495 (5)
O3	0.4810 (2)	0.73064 (12)	0.31740 (11)	0.0388 (4)
C11	0.6745 (2)	0.85748 (16)	0.45063 (13)	0.0239 (4)
C12	0.5996 (3)	0.89811 (16)	0.36185 (14)	0.0251 (4)
C13	0.5832 (3)	1.00790 (17)	0.34180 (16)	0.0341 (5)
H13	0.5322	1.0317	0.2818	0.041*
C14	0.6439 (3)	1.08187 (18)	0.41256 (18)	0.0405 (5)
H14	0.6340	1.1562	0.4004	0.049*
C15	0.7190 (3)	1.04525 (17)	0.50114 (18)	0.0383 (5)
H15	0.7598	1.0952	0.5485	0.046*
C16	0.7347 (3)	0.93358 (17)	0.52071 (16)	0.0321 (5)
H16	0.7856	0.9101	0.5808	0.038*
C21	0.6503 (3)	0.57434 (16)	0.56687 (14)	0.0246 (4)
C22	0.6130 (3)	0.54470 (17)	0.66744 (14)	0.0284 (4)
C23	0.6223 (3)	0.43408 (19)	0.69291 (17)	0.0384 (5)
H23	0.5968	0.4124	0.7590	0.046*
C24	0.6687 (4)	0.35605 (18)	0.62128 (18)	0.0417 (6)
H24	0.6756	0.2831	0.6399	0.050*
C25	0.7045 (3)	0.38710 (17)	0.52281 (17)	0.0392 (5)
H25	0.7353	0.3349	0.4749	0.047*
C26	0.6949 (3)	0.49615 (17)	0.49469 (15)	0.0316 (5)
H26	0.7181	0.5168	0.4280	0.038*
C27	0.5619 (3)	0.6283 (2)	0.74710 (14)	0.0365 (5)
H27A	0.6471	0.6846	0.7501	0.055*
H27B	0.5531	0.5935	0.8124	0.055*
H27C	0.4533	0.6595	0.7292	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0313 (9)	0.0204 (8)	0.0201 (8)	0.0029 (7)	0.0025 (7)	0.0010 (6)
C1	0.0261 (10)	0.0223 (9)	0.0198 (8)	−0.0011 (8)	−0.0039 (7)	−0.0026 (7)
O1	0.0326 (8)	0.0226 (7)	0.0278 (7)	−0.0013 (6)	0.0060 (6)	−0.0034 (5)
N2	0.0338 (9)	0.0316 (10)	0.0251 (8)	0.0001 (8)	−0.0025 (7)	0.0009 (7)
O2	0.0736 (13)	0.0524 (10)	0.0226 (7)	−0.0003 (10)	−0.0107 (8)	0.0060 (7)
O3	0.0504 (10)	0.0302 (7)	0.0358 (7)	−0.0138 (7)	−0.0059 (7)	−0.0001 (6)
C11	0.0259 (10)	0.0206 (9)	0.0252 (9)	0.0001 (8)	0.0029 (8)	−0.0013 (7)
C12	0.0259 (10)	0.0244 (10)	0.0250 (9)	−0.0034 (8)	0.0018 (8)	0.0009 (7)
C13	0.0388 (12)	0.0262 (11)	0.0373 (10)	0.0009 (9)	0.0015 (10)	0.0096 (9)
C14	0.0439 (13)	0.0210 (10)	0.0565 (14)	0.0021 (10)	−0.0018 (11)	0.0034 (10)
C15	0.0425 (13)	0.0233 (10)	0.0492 (13)	−0.0015 (10)	−0.0036 (11)	−0.0101 (9)
C16	0.0377 (12)	0.0271 (10)	0.0314 (10)	0.0034 (9)	−0.0054 (9)	−0.0050 (8)
C21	0.0274 (10)	0.0224 (9)	0.0242 (8)	0.0002 (8)	−0.0025 (8)	0.0036 (7)
C22	0.0311 (10)	0.0300 (10)	0.0241 (9)	0.0019 (9)	−0.0024 (8)	0.0053 (8)
C23	0.0465 (13)	0.0357 (12)	0.0330 (10)	0.0005 (10)	−0.0003 (10)	0.0134 (9)
C24	0.0532 (14)	0.0230 (10)	0.0490 (12)	0.0001 (11)	0.0022 (12)	0.0116 (10)
C25	0.0522 (14)	0.0231 (10)	0.0422 (11)	−0.0016 (10)	0.0020 (11)	−0.0017 (9)
C26	0.0439 (13)	0.0230 (9)	0.0278 (10)	−0.0016 (9)	0.0016 (9)	0.0020 (8)
C27	0.0451 (13)	0.0436 (13)	0.0209 (9)	0.0077 (11)	0.0032 (9)	0.0031 (9)

Geometric parameters (Å, º)

N1—C1	1.345 (2)	C15—H15	0.9300
N1—C21	1.433 (2)	C16—H16	0.9300
N1—H1	0.92 (3)	C21—C26	1.394 (3)
C1—O1	1.234 (2)	C21—C22	1.401 (3)
C1—C11	1.515 (3)	C22—C23	1.401 (3)
N2—O2	1.228 (2)	C22—C27	1.519 (3)
N2—O3	1.231 (2)	C23—C24	1.391 (3)
N2—C12	1.480 (3)	C23—H23	0.9300
C11—C16	1.393 (3)	C24—C25	1.377 (3)
C11—C12	1.397 (3)	C24—H24	0.9300
C12—C13	1.380 (3)	C25—C26	1.392 (3)
C13—C14	1.384 (3)	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300
C14—C15	1.379 (3)	C27—H27A	0.9600
C14—H14	0.9300	C27—H27B	0.9600
C15—C16	1.401 (3)	C27—H27C	0.9600
C1—N1—C21	126.20 (17)	C15—C16—H16	119.8
C1—N1—H1	117.5 (15)	C26—C21—C22	120.94 (18)
C21—N1—H1	116.1 (16)	C26—C21—N1	121.32 (16)
O1—C1—N1	125.21 (18)	C22—C21—N1	117.68 (17)
O1—C1—C11	119.02 (17)	C21—C22—C23	117.80 (19)
N1—C1—C11	115.63 (16)	C21—C22—C27	121.89 (18)
O2—N2—O3	123.79 (18)	C23—C22—C27	120.30 (18)
O2—N2—C12	117.91 (17)	C24—C23—C22	121.35 (19)
O3—N2—C12	118.30 (16)	C24—C23—H23	119.3
C16—C11—C12	116.93 (18)	C22—C23—H23	119.3
C16—C11—C1	119.92 (16)	C25—C24—C23	119.8 (2)
C12—C11—C1	122.37 (16)	C25—C24—H24	120.1
C13—C12—C11	123.19 (18)	C23—C24—H24	120.1
C13—C12—N2	117.73 (18)	C24—C25—C26	120.3 (2)
C11—C12—N2	119.03 (17)	C24—C25—H25	119.8
C12—C13—C14	118.8 (2)	C26—C25—H25	119.8
C12—C13—H13	120.6	C25—C26—C21	119.76 (19)
C14—C13—H13	120.6	C25—C26—H26	120.1
C15—C14—C13	119.9 (2)	C21—C26—H26	120.1
C15—C14—H14	120.1	C22—C27—H27A	109.5
C13—C14—H14	120.1	C22—C27—H27B	109.5
C14—C15—C16	120.8 (2)	H27A—C27—H27B	109.5
C14—C15—H15	119.6	C22—C27—H27C	109.5
C16—C15—H15	119.6	H27A—C27—H27C	109.5
C11—C16—C15	120.4 (2)	H27B—C27—H27C	109.5
C11—C16—H16	119.8
C21—N1—C1—O1	−5.4 (3)	C13—C14—C15—C16	−0.1 (4)
C21—N1—C1—C11	178.96 (17)	C12—C11—C16—C15	0.0 (3)
O1—C1—C11—C16	−103.0 (2)	C1—C11—C16—C15	170.1 (2)
N1—C1—C11—C16	72.9 (2)	C14—C15—C16—C11	0.1 (4)
O1—C1—C11—C12	66.5 (3)	C1—N1—C21—C26	−27.7 (3)
N1—C1—C11—C12	−117.6 (2)	C1—N1—C21—C22	154.78 (19)
C16—C11—C12—C13	−0.2 (3)	C26—C21—C22—C23	0.1 (3)
C1—C11—C12—C13	−170.0 (2)	N1—C21—C22—C23	177.60 (19)
C16—C11—C12—N2	−177.46 (18)	C26—C21—C22—C27	−179.2 (2)
C1—C11—C12—N2	12.7 (3)	N1—C21—C22—C27	−1.7 (3)
O2—N2—C12—C13	26.3 (3)	C21—C22—C23—C24	0.7 (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—C11	24.7 (3)	C23—C24—C25—C26	0.2 (4)
C11—C12—C13—C14	0.2 (3)	C24—C25—C26—C21	0.6 (4)
N2—C12—C13—C14	177.49 (19)	C22—C21—C26—C25	−0.7 (3)
C12—C13—C14—C15	0.0 (3)	N1—C21—C26—C25	−178.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.92 (3)	1.99 (3)	2.849 (2)	155 (2)

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