N-(2-Methoxy-phen-yl)-2-nitro-benzamide.

Geometric parameters of the title compound, C(14)H(12)N(2)O(4), 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.

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 ▶).

Experimental

Crystal data

C14H12N2O4

M = 272.26

Orthorhombic,

a = 7.6467 (11) Å

b = 9.9272 (8) Å

c = 16.5032 (14) Å

V = 1252.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 (2) K

0.37 × 0.33 × 0.21 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: none

8342 measured reflections

1368 independent reflections

1275 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.110

S = 1.05

1368 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002626/ez2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002626/ez2111Isup2.hkl

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

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 = 3.8–25.6º
b = 9.9272 (8) Å	µ = 0.11 mm−1
c = 16.5032 (14) Å	T = 173 (2) K
V = 1252.8 (2) Å3	Block, light yellow
Z = 4	0.37 × 0.33 × 0.21 mm
F000 = 568

Stoe IPDSII two-circle diffractometer	1275 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Monochromator: graphite	θmax = 25.6º
T = 173(2) K	θmin = 3.6º
ω scans	h = −7→9
Absorption correction: none	k = −12→12
8342 measured reflections	l = −20→18
1368 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H 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 = 1.05	Δρmax = 0.28 e Å−3
1368 reflections	Δρmin = −0.21 e Å−3
187 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.052 (7)
Secondary atom site location: difference Fourier map

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.

	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*

	U11	U22	U33	U12	U13	U23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.82 (4)	2.57 (4)	3.352 (3)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.82 (4)	2.57 (4)	3.352 (3)	159 (3)

Symmetry code: (i) .