N-(2-Methyl­phen­yl)-2-nitro­benzamide

Saeed, A.; Hussain, S.; Bolte, M.

doi:10.1107/S1600536808002298

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o521

doi:10.1107/S1600536808002298

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N-(2-Methylphenyl)-2-nitrobenzamide

Aamer Saeed,^a Shahid Hussain ^a and Michael Bolte ^b ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 12 January 2008; accepted 22 January 2008; online 25 January 2008)

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 ); 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 ).

Experimental

Crystal data

C₁₄H₁₂N₂O₃
M_r = 256.26
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.077
S = 1.02
1364 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.92 (3)	1.99 (3)	2.849 (2)	155 (2)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

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

Supporting information

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

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

checkCIF report

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 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 top

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).

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

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

N-(2-Methylphenyl)-2-nitrobenzamide top

Crystal data top

C₁₄H₁₂N₂O₃	F(000) = 536
M_r = 256.26	D_x = 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) Å³	Needle, light brown
Z = 4	0.35 × 0.14 × 0.13 mm

Data collection top

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

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0533P)² + 0.0696P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
1364 reflections	Δρ_max = 0.13 e Å⁻³
178 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (3)

Crystal data top

C₁₄H₁₂N₂O₃	V = 1259.7 (2) Å³
M_r = 256.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.8063 (10) Å	µ = 0.10 mm⁻¹
b = 12.2856 (11) Å	T = 273 K
c = 13.1353 (13) Å	0.35 × 0.14 × 0.13 mm

Data collection top

Stoe IPDSII two-circle diffractometer	1243 reflections with I > 2σ(I)
4741 measured reflections	R_int = 0.036
1364 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.13 e Å⁻³
1364 reflections	Δρ_min = −0.14 e Å⁻³
178 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
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.92 (3)	1.99 (3)	2.849 (2)	155 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂O₃
M_r	256.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	273
a, b, c (Å)	7.8063 (10), 12.2856 (11), 13.1353 (13)
V (Å³)	1259.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.14 × 0.13

Data collection
Diffractometer	Stoe IPDSII two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4741, 1364, 1243
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.078, 1.02
No. of reflections	1364
No. of parameters	178
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.92 (3)	1.99 (3)	2.849 (2)	155 (2)

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

Acknowledgements

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

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