4-Meth-oxy-N-(2-nitro-benzyl-idene)aniline.

The title compound, C(14)H(12)N(2)O(3), was prepared by reaction of 2-nitro-benzaldehyde with 4-methoxy-benzenamine at 377 K. The molecule has an E configuration, with a dihedral angle between the two benzene rings of 43.3 (5)°. An intermolecular C-H⋯O interaction links molecules in zigzag chains down the a axis.

Related literature

For the properties of Schiff bases, see: Deschamps et al. (2003 ▶); Tarafder et al. (2000 ▶); Rozwadowski et al. (1999 ▶). For related structures, see: Jian et al. (2006 ▶); Rozwadowski et al. (1999 ▶); Tarafder et al. (2000 ▶).

Experimental

Crystal data

C14H12N2O3

M = 256.26

Orthorhombic,

a = 4.0010 (8) Å

b = 7.8410 (16) Å

c = 40.447 (8) Å

V = 1268.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.20 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

3103 measured reflections

1651 independent reflections

748 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.135

S = 0.96

1651 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025117/at2599sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025117/at2599Isup2.hkl

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

C14H12N2O3	F(000) = 536
Mr = 256.26	Dx = 1.341 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1121 reflections
a = 4.0010 (8) Å	θ = 1.0–27.0°
b = 7.8410 (16) Å	µ = 0.10 mm−1
c = 40.447 (8) Å	T = 293 K
V = 1268.9 (4) Å3	Block, yellow
Z = 4	0.20 × 0.15 × 0.11 mm

Bruker SMART CCD area-detector diffractometer	748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.087
graphite	θmax = 27.0°, θmin = 1.0°
phi and ω scans	h = −4→0
3103 measured reflections	k = −9→9
1651 independent reflections	l = 0→48

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0597P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
1651 reflections	Δρmax = 0.22 e Å−3
173 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (3)

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
O3	0.5842 (9)	0.0957 (4)	0.02919 (6)	0.0602 (10)
C10	0.8225 (12)	−0.3220 (5)	0.08753 (10)	0.0421 (12)
N2	0.9205 (10)	−0.4713 (4)	0.10536 (8)	0.0506 (11)
C13	0.6562 (12)	−0.0364 (5)	0.05006 (10)	0.0431 (11)
C4	1.0942 (12)	−0.5998 (5)	0.15664 (10)	0.0433 (12)
C11	0.8984 (13)	−0.3162 (5)	0.05408 (9)	0.0482 (12)
H11A	1.0036	−0.4083	0.0440	0.058*
C12	0.8172 (13)	−0.1730 (5)	0.03578 (10)	0.0505 (13)
H12A	0.8723	−0.1689	0.0135	0.061*
C3	1.2227 (13)	−0.5869 (5)	0.18867 (9)	0.0455 (12)
C9	0.6573 (12)	−0.1861 (5)	0.10172 (10)	0.0438 (12)
H9A	0.6033	−0.1899	0.1241	0.053*
O2	1.4501 (11)	−0.3130 (4)	0.18665 (8)	0.0813 (13)
C8	0.5695 (12)	−0.0423 (5)	0.08302 (10)	0.0471 (13)
H8A	0.4543	0.0477	0.0927	0.056*
N1	1.2977 (13)	−0.4173 (5)	0.20309 (10)	0.0623 (12)
C6	1.1071 (14)	−0.9039 (5)	0.16521 (12)	0.0654 (16)
H6A	1.0707	−1.0130	0.1569	0.078*
C7	1.0088 (11)	−0.4530 (5)	0.13540 (10)	0.0460 (12)
H7A	1.0199	−0.3436	0.1442	0.055*
C5	1.0397 (13)	−0.7655 (5)	0.14548 (10)	0.0546 (14)
H5A	0.9560	−0.7828	0.1243	0.065*
C14	0.4282 (15)	0.2451 (5)	0.04323 (11)	0.0698 (16)
H14A	0.3941	0.3287	0.0262	0.105*
H14B	0.5701	0.2918	0.0601	0.105*
H14C	0.2167	0.2143	0.0527	0.105*
C2	1.2840 (15)	−0.7234 (6)	0.20893 (11)	0.0627 (16)
H2B	1.3624	−0.7074	0.2303	0.075*
O1	1.2071 (14)	−0.3908 (5)	0.23092 (9)	0.1181 (19)
C1	1.2268 (16)	−0.8852 (6)	0.19681 (12)	0.0712 (17)
H1A	1.2689	−0.9804	0.2099	0.085*

	U11	U22	U33	U12	U13	U23
O3	0.069 (2)	0.0526 (16)	0.0587 (19)	0.010 (2)	−0.0010 (19)	0.0113 (16)
C10	0.040 (3)	0.040 (2)	0.047 (3)	−0.006 (3)	−0.006 (3)	0.001 (2)
N2	0.054 (3)	0.052 (2)	0.046 (2)	−0.002 (2)	−0.007 (2)	0.0026 (18)
C13	0.043 (3)	0.042 (2)	0.045 (3)	−0.002 (3)	−0.007 (3)	0.000 (2)
C4	0.043 (3)	0.048 (2)	0.039 (2)	0.002 (3)	0.003 (2)	−0.003 (2)
C11	0.054 (3)	0.046 (2)	0.044 (3)	−0.004 (3)	0.006 (3)	−0.009 (2)
C12	0.056 (4)	0.058 (3)	0.037 (2)	−0.001 (3)	0.001 (3)	0.007 (2)
C3	0.053 (3)	0.044 (2)	0.040 (2)	−0.003 (3)	0.001 (2)	−0.004 (2)
C9	0.041 (3)	0.053 (2)	0.038 (2)	0.003 (3)	−0.007 (2)	0.001 (2)
O2	0.103 (4)	0.064 (2)	0.078 (2)	−0.020 (3)	−0.007 (3)	−0.0003 (19)
C8	0.048 (3)	0.048 (3)	0.045 (3)	−0.001 (3)	−0.001 (3)	−0.006 (2)
N1	0.077 (3)	0.067 (3)	0.043 (2)	0.003 (3)	−0.003 (3)	0.002 (2)
C6	0.079 (4)	0.045 (3)	0.072 (3)	0.000 (3)	−0.007 (3)	−0.001 (3)
C7	0.037 (3)	0.045 (3)	0.056 (3)	−0.001 (2)	0.000 (3)	0.000 (2)
C5	0.060 (4)	0.050 (3)	0.054 (3)	0.001 (3)	−0.007 (3)	0.000 (2)
C14	0.073 (4)	0.055 (3)	0.081 (3)	0.010 (4)	−0.019 (3)	0.014 (3)
C2	0.078 (4)	0.064 (3)	0.047 (3)	0.014 (3)	−0.005 (3)	0.005 (2)
O1	0.181 (5)	0.108 (3)	0.065 (2)	−0.024 (4)	0.010 (3)	−0.029 (2)
C1	0.089 (4)	0.061 (3)	0.064 (3)	0.012 (4)	−0.010 (4)	0.017 (3)

O3—C13	1.367 (4)	C9—C8	1.402 (5)
O3—C14	1.444 (5)	C9—H9A	0.9300
C10—C9	1.379 (5)	O2—N1	1.217 (5)
C10—C11	1.387 (5)	C8—H8A	0.9300
C10—N2	1.430 (5)	N1—O1	1.201 (5)
N2—C7	1.274 (5)	C6—C1	1.373 (6)
C13—C12	1.376 (5)	C6—C5	1.373 (5)
C13—C8	1.379 (5)	C6—H6A	0.9300
C4—C5	1.393 (5)	C7—H7A	0.9300
C4—C3	1.398 (5)	C5—H5A	0.9300
C4—C7	1.477 (5)	C14—H14A	0.9600
C11—C12	1.384 (5)	C14—H14B	0.9600
C11—H11A	0.9300	C14—H14C	0.9600
C12—H12A	0.9300	C2—C1	1.378 (6)
C3—C2	1.370 (5)	C2—H2B	0.9300
C3—N1	1.482 (5)	C1—H1A	0.9300
C13—O3—C14	117.6 (3)	C9—C8—H8A	120.5
C9—C10—C11	119.0 (4)	O1—N1—O2	123.2 (5)
C9—C10—N2	123.7 (4)	O1—N1—C3	117.5 (4)
C11—C10—N2	117.3 (4)	O2—N1—C3	119.3 (4)
C7—N2—C10	117.7 (3)	C1—C6—C5	121.7 (4)
O3—C13—C12	115.4 (4)	C1—C6—H6A	119.2
O3—C13—C8	124.7 (4)	C5—C6—H6A	119.2
C12—C13—C8	119.8 (4)	N2—C7—C4	122.1 (4)
C5—C4—C3	115.2 (4)	N2—C7—H7A	119.0
C5—C4—C7	120.2 (4)	C4—C7—H7A	119.0
C3—C4—C7	124.6 (4)	C6—C5—C4	121.2 (4)
C12—C11—C10	119.8 (4)	C6—C5—H5A	119.4
C12—C11—H11A	120.1	C4—C5—H5A	119.4
C10—C11—H11A	120.1	O3—C14—H14A	109.5
C13—C12—C11	121.1 (4)	O3—C14—H14B	109.5
C13—C12—H12A	119.4	H14A—C14—H14B	109.5
C11—C12—H12A	119.4	O3—C14—H14C	109.5
C2—C3—C4	124.3 (4)	H14A—C14—H14C	109.5
C2—C3—N1	115.4 (4)	H14B—C14—H14C	109.5
C4—C3—N1	120.3 (4)	C3—C2—C1	118.5 (4)
C10—C9—C8	121.1 (4)	C3—C2—H2B	120.8
C10—C9—H9A	119.4	C1—C2—H2B	120.8
C8—C9—H9A	119.4	C6—C1—C2	119.2 (5)
C13—C8—C9	119.1 (4)	C6—C1—H1A	120.4
C13—C8—H8A	120.5	C2—C1—H1A	120.4

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O3i	0.96	2.63	3.469 (5)	146.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O3i	0.93	2.63	3.469 (5)	146

Symmetry code: (i) .