4-Meth­oxy-N-(2-nitro­benzyl­idene)aniline

Ren, X.-Y.; Jian, F.-F.

doi:10.1107/S1600536808025117

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2027

doi:10.1107/S1600536808025117

Open

access

4-Methoxy-N-(2-nitrobenzylidene)aniline

Xiao-Yan Ren ^a and Fang-Fang Jian ^a ^*

^aMicroscale Science Institute , Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 17 July 2008; accepted 5 August 2008; online 27 September 2008)

The title compound, C₁₄H₁₂N₂O₃, was prepared by reaction of 2-nitrobenzaldehyde with 4-methoxybenzenamine 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_r = 256.26
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.135
S = 0.96
1651 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Schiff bases have antimicrobial (Tarafder et al., 2000) and anticancer applications (Deschamps et al., 2003). The recent growing interest in Schiff bases is also due to their ability to form intramolecular hydrogen bonds by electron coupling between acid-base centers (Rozwadowski et al., 1999). The aim of our research is to find Schiff base with higher biological activity. Therefore we sythesized the title compound (I) and report its crystal structure here.

In the crystal structure of (I) (Fig. 1), the dihedral angle formed by the phenyl rings (C1–C6) and (C8–C13) was 43.3 (2)°. The C?N bond length [1.274 (5) Å] is in agreement with that observed before (Jian et al., 2006). In the structure, there are no classical hydrogen bonds. Only, one intramolecular C–H···O type hydrogen bonding contact exists (Table 1).

Related literature top

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

Experimental top

A mixture of 2-nitrobenzaldehyde (0.02 mol) and 4-methoxybenzenamine (0.02 mol) was stirred with ethanol (50 mL) at 377 K for 5 h, affording the title compound (4.33 g, yield 84.5%). Single crystals suitable for X-ray measurements were obtained by recrystallization from acetone at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.

4-Methoxy-N-(2-nitrobenzylidene)aniline top

Crystal data top

C₁₄H₁₂N₂O₃	F(000) = 536
M_r = 256.26	D_x = 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

Data collection top

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

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)] = 0.052	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0597P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
1651 reflections	Δρ_max = 0.22 e Å⁻³
173 parameters	Δρ_min = −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)

Crystal data top

C₁₄H₁₂N₂O₃	V = 1268.9 (4) Å³
M_r = 256.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.0010 (8) Å	µ = 0.10 mm⁻¹
b = 7.8410 (16) Å	T = 293 K
c = 40.447 (8) Å	0.20 × 0.15 × 0.11 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	748 reflections with I > 2σ(I)
3103 measured reflections	R_int = 0.087
1651 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 0.96	Δρ_max = 0.22 e Å⁻³
1651 reflections	Δρ_min = −0.24 e Å⁻³
173 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x−1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂O₃
M_r	256.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	4.0010 (8), 7.8410 (16), 40.447 (8)
V (Å³)	1268.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.15 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3103, 1651, 748
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.135, 0.96
No. of reflections	1651
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O3ⁱ	0.96	2.63	3.469 (5)	146.3

Symmetry code: (i) x−1/2, −y+1/2, −z.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Deschamps, P., Kulkarni, P. P. & Sarkar, B. (2003). Inorg. Chem. 42, 7366–7368. Web of Science CSD CrossRef PubMed CAS Google Scholar
Jian, F.-F., Zhuang, R.-R., Wang, K.-F., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o3198–o3199. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rozwadowski, Z., Majewski, E., Dziembowska, T. & Hansen, P. E. (1999). Chem. Soc. Perkin Trans. 2, pp. 2809–2817. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tarafder, M. T. H., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem. 25, 456–460. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2027

doi:10.1107/S1600536808025117

Open

access