N-(2-Methoxy­phen­yl)-2-nitro­benzamide

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.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.111
• Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.32
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

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           25.62
           From the CIF: _reflns_number_total               1368
           Count of symmetry unique reflns         1387
           Completeness (_total/calc)             98.63%
           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
   2 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
   2 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 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

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).

S2. Experimental

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).

S3. Refinement

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 U_eq(C) or U(H) = 1.5 U_eq(C_methyl)] 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

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 the title compound.

N-(2-Methoxyphenyl)-2-nitrobenzamide

Crystal data

C14H12N2O4	Dx = 1.444 Mg m^−3
Mr = 272.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 7856 reflections
a = 7.6467 (11) Å	θ = 3.8–25.6°
b = 9.9272 (8) Å	µ = 0.11 mm^−1
c = 16.5032 (14) Å	T = 173 K
V = 1252.8 (2) Å^3	Block, light yellow
Z = 4	0.37 × 0.33 × 0.21 mm
F(000) = 568

Data collection

Stoe IPDSII two-circle diffractometer	1275 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Graphite monochromator	θmax = 25.6°, θmin = 3.6°
ω scans	h = −7→9
8342 measured reflections	k = −12→12
1368 independent reflections	l = −20→18

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0824P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1368 reflections	Δρmax = 0.28 e Å^−3
187 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.052 (7)

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
C1	0.7040 (3)	0.4189 (2)	0.58905 (15)	0.0271 (5)
N1	0.6935 (3)	0.46807 (19)	0.51339 (14)	0.0287 (5)
H1	0.618 (5)	0.449 (3)	0.4799 (19)	0.040 (9)*
N2	0.7600 (3)	0.14453 (18)	0.64422 (13)	0.0299 (5)
O1	0.8235 (3)	0.44489 (17)	0.63779 (11)	0.0370 (5)
O2	0.8450 (3)	0.16188 (18)	0.58190 (13)	0.0410 (5)
O3	0.8114 (3)	0.07915 (18)	0.70333 (13)	0.0419 (5)
O4	0.5752 (2)	0.62521 (16)	0.39737 (11)	0.0305 (5)
C11	0.5537 (3)	0.3307 (2)	0.61508 (14)	0.0263 (5)
C12	0.5833 (3)	0.2030 (2)	0.64870 (16)	0.0264 (5)
C13	0.4498 (4)	0.1261 (2)	0.68256 (15)	0.0307 (6)
H13	0.4744	0.0404	0.7055	0.037*
C14	0.2795 (4)	0.1764 (2)	0.68236 (17)	0.0338 (6)
H14	0.1869	0.1248	0.7049	0.041*
C15	0.2456 (4)	0.3028 (3)	0.64891 (17)	0.0360 (6)
H15	0.1294	0.3368	0.6483	0.043*
C16	0.3821 (4)	0.3800 (2)	0.61615 (17)	0.0324 (6)
H16	0.3579	0.4667	0.5945	0.039*
C21	0.8150 (3)	0.5560 (2)	0.47494 (14)	0.0260 (5)
C22	0.7505 (3)	0.6385 (2)	0.41263 (15)	0.0267 (5)
C23	0.8635 (4)	0.7254 (2)	0.37131 (16)	0.0293 (6)
H23	0.8199	0.7825	0.3297	0.035*
C24	1.0410 (4)	0.7277 (2)	0.39163 (16)	0.0314 (6)
H24	1.1177	0.7872	0.3638	0.038*
C25	1.1068 (4)	0.6440 (2)	0.45211 (17)	0.0323 (6)
H25	1.2280	0.6452	0.4649	0.039*
C26	0.9933 (4)	0.5579 (2)	0.49399 (15)	0.0299 (5)
H26	1.0374	0.5007	0.5354	0.036*
C27	0.5074 (4)	0.6982 (2)	0.32917 (16)	0.0323 (6)
H27A	0.5211	0.7951	0.3385	0.048*
H27B	0.3831	0.6769	0.3222	0.048*
H27C	0.5717	0.6724	0.2802	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0227 (13)	0.0256 (10)	0.0331 (13)	0.0022 (9)	−0.0009 (10)	−0.0013 (9)
N1	0.0195 (11)	0.0312 (10)	0.0354 (12)	−0.0040 (8)	−0.0015 (10)	0.0024 (8)
N2	0.0261 (12)	0.0246 (9)	0.0390 (12)	0.0014 (9)	−0.0020 (9)	−0.0034 (8)
O1	0.0324 (11)	0.0415 (9)	0.0372 (10)	−0.0095 (9)	−0.0085 (8)	0.0057 (8)
O2	0.0308 (11)	0.0429 (9)	0.0491 (11)	0.0067 (8)	0.0110 (9)	0.0029 (9)
O3	0.0413 (12)	0.0373 (8)	0.0470 (12)	0.0104 (9)	−0.0093 (9)	0.0037 (8)
O4	0.0209 (9)	0.0330 (8)	0.0374 (10)	−0.0019 (7)	−0.0012 (8)	0.0062 (7)
C11	0.0217 (12)	0.0282 (11)	0.0289 (12)	0.0003 (10)	−0.0005 (11)	0.0009 (9)
C12	0.0208 (14)	0.0269 (10)	0.0315 (12)	−0.0008 (9)	0.0007 (10)	−0.0038 (9)
C13	0.0312 (15)	0.0271 (10)	0.0338 (13)	−0.0040 (10)	0.0025 (12)	−0.0029 (9)
C14	0.0268 (15)	0.0368 (12)	0.0377 (14)	−0.0069 (11)	0.0047 (12)	−0.0027 (10)
C15	0.0216 (14)	0.0457 (13)	0.0408 (15)	0.0011 (11)	0.0024 (12)	−0.0023 (11)
C16	0.0255 (14)	0.0355 (12)	0.0362 (13)	0.0055 (10)	0.0001 (12)	0.0043 (10)
C21	0.0216 (12)	0.0247 (10)	0.0315 (12)	−0.0026 (10)	0.0041 (10)	0.0000 (9)
C22	0.0210 (12)	0.0261 (10)	0.0328 (12)	−0.0010 (9)	0.0016 (10)	−0.0011 (9)
C23	0.0270 (14)	0.0264 (10)	0.0345 (13)	−0.0007 (10)	0.0036 (11)	0.0005 (9)
C24	0.0247 (14)	0.0304 (11)	0.0390 (14)	−0.0047 (10)	0.0044 (12)	−0.0004 (10)
C25	0.0225 (13)	0.0345 (12)	0.0398 (13)	−0.0043 (11)	−0.0005 (11)	−0.0034 (10)
C26	0.0243 (13)	0.0328 (12)	0.0326 (12)	0.0005 (11)	−0.0010 (10)	−0.0008 (9)
C27	0.0240 (14)	0.0362 (12)	0.0367 (14)	0.0010 (10)	−0.0036 (11)	0.0074 (9)

Geometric parameters (Å, º)

C1—O1	1.244 (3)	C15—C16	1.404 (4)
C1—N1	1.343 (3)	C15—H15	0.9500
C1—C11	1.508 (3)	C16—H16	0.9500
N1—C21	1.424 (3)	C21—C26	1.399 (4)
N1—H1	0.82 (4)	C21—C22	1.404 (3)
N2—O2	1.229 (3)	C22—C23	1.399 (3)
N2—O3	1.236 (3)	C23—C24	1.399 (4)
N2—C12	1.473 (3)	C23—H23	0.9500
O4—C22	1.371 (3)	C24—C25	1.393 (4)
O4—C27	1.435 (3)	C24—H24	0.9500
C11—C16	1.400 (4)	C25—C26	1.401 (4)
C11—C12	1.402 (3)	C25—H25	0.9500
C12—C13	1.392 (4)	C26—H26	0.9500
C13—C14	1.395 (4)	C27—H27A	0.9800
C13—H13	0.9500	C27—H27B	0.9800
C14—C15	1.395 (4)	C27—H27C	0.9800
C14—H14	0.9500
O1—C1—N1	124.7 (2)	C11—C16—H16	119.6
O1—C1—C11	119.7 (2)	C15—C16—H16	119.6
N1—C1—C11	115.5 (2)	C26—C21—C22	119.9 (2)
C1—N1—C21	126.7 (2)	C26—C21—N1	122.9 (2)
C1—N1—H1	126 (2)	C22—C21—N1	117.1 (2)
C21—N1—H1	107 (2)	O4—C22—C23	125.0 (2)
O2—N2—O3	124.5 (2)	O4—C22—C21	115.0 (2)
O2—N2—C12	118.2 (2)	C23—C22—C21	120.0 (2)
O3—N2—C12	117.3 (2)	C22—C23—C24	119.5 (2)
C22—O4—C27	116.69 (19)	C22—C23—H23	120.2
C16—C11—C12	117.5 (2)	C24—C23—H23	120.2
C16—C11—C1	121.0 (2)	C25—C24—C23	120.8 (2)
C12—C11—C1	121.0 (2)	C25—C24—H24	119.6
C13—C12—C11	122.5 (2)	C23—C24—H24	119.6
C13—C12—N2	118.5 (2)	C24—C25—C26	119.6 (3)
C11—C12—N2	119.0 (2)	C24—C25—H25	120.2
C12—C13—C14	119.1 (2)	C26—C25—H25	120.2
C12—C13—H13	120.4	C21—C26—C25	120.1 (2)
C14—C13—H13	120.4	C21—C26—H26	120.0
C13—C14—C15	119.8 (2)	C25—C26—H26	120.0
C13—C14—H14	120.1	O4—C27—H27A	109.5
C15—C14—H14	120.1	O4—C27—H27B	109.5
C14—C15—C16	120.3 (3)	H27A—C27—H27B	109.5
C14—C15—H15	119.8	O4—C27—H27C	109.5
C16—C15—H15	119.8	H27A—C27—H27C	109.5
C11—C16—C15	120.7 (2)	H27B—C27—H27C	109.5
O1—C1—N1—C21	0.8 (4)	C12—C11—C16—C15	−0.8 (4)
C11—C1—N1—C21	178.3 (2)	C1—C11—C16—C15	−172.8 (2)
O1—C1—C11—C16	118.2 (3)	C14—C15—C16—C11	1.2 (4)
N1—C1—C11—C16	−59.5 (3)	C1—N1—C21—C26	29.1 (4)
O1—C1—C11—C12	−53.6 (3)	C1—N1—C21—C22	−154.1 (2)
N1—C1—C11—C12	128.8 (2)	C27—O4—C22—C23	5.6 (3)
C16—C11—C12—C13	−0.2 (4)	C27—O4—C22—C21	−174.3 (2)
C1—C11—C12—C13	171.8 (2)	C26—C21—C22—O4	177.9 (2)
C16—C11—C12—N2	176.4 (2)	N1—C21—C22—O4	1.0 (3)
C1—C11—C12—N2	−11.6 (3)	C26—C21—C22—C23	−2.0 (3)
O2—N2—C12—C13	138.0 (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—C24	1.1 (4)
O3—N2—C12—C11	142.4 (2)	C22—C23—C24—C25	0.4 (4)
C11—C12—C13—C14	0.8 (4)	C23—C24—C25—C26	−1.0 (4)
N2—C12—C13—C14	−175.8 (2)	C22—C21—C26—C25	1.3 (4)
C12—C13—C14—C15	−0.4 (4)	N1—C21—C26—C25	178.0 (2)
C13—C14—C15—C16	−0.6 (4)	C24—C25—C26—C21	0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.82 (4)	2.57 (4)	3.352 (3)	159 (3)

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