organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Deschamps, P., Kulkarni, P. P. & Sarkar, B. (2003). Inorg. Chem. 42, 7366-7368.]); Tarafder et al. (2000[Tarafder, M. T. H., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem. 25, 456-460.]); Rozwadowski et al. (1999[Rozwadowski, Z., Majewski, E., Dziembowska, T. & Hansen, P. E. (1999). Chem. Soc. Perkin Trans. 2, pp. 2809-2817.]). For related structures, see: Jian et al. (2006[Jian, F.-F., Zhuang, R.-R., Wang, K.-F., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o3198-o3199.]); Rozwadowski et al. (1999[Rozwadowski, Z., Majewski, E., Dziembowska, T. & Hansen, P. E. (1999). Chem. Soc. Perkin Trans. 2, pp. 2809-2817.]); Tarafder et al. (2000[Tarafder, M. T. H., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem. 25, 456-460.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12N2O3

  • Mr = 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)

  • Rint = 0.087

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 and 0.96 Å, and with Uiso(H) = 1.2 or 1.5Ueq of the parent atoms. In the absence of significant anomalous scattering effects, Friedel pairs have been merged.

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
[Figure 1] 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
C14H12N2O3F(000) = 536
Mr = 256.26Dx = 1.341 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1121 reflections
a = 4.0010 (8) Åθ = 1.0–27.0°
b = 7.8410 (16) ŵ = 0.10 mm1
c = 40.447 (8) ÅT = 293 K
V = 1268.9 (4) Å3Block, yellow
Z = 40.20 × 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 tubeRint = 0.087
Graphite monochromatorθmax = 27.0°, θmin = 1.0°
phi and ω scansh = 40
3103 measured reflectionsk = 99
1651 independent reflectionsl = 048
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-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 reflectionsΔρmax = 0.22 e Å3
173 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (3)
Crystal data top
C14H12N2O3V = 1268.9 (4) Å3
Mr = 256.26Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.0010 (8) ŵ = 0.10 mm1
b = 7.8410 (16) ÅT = 293 K
c = 40.447 (8) Å0.20 × 0.15 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
748 reflections with I > 2σ(I)
3103 measured reflectionsRint = 0.087
1651 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 0.96Δρmax = 0.22 e Å3
1651 reflectionsΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
O30.5842 (9)0.0957 (4)0.02919 (6)0.0602 (10)
C100.8225 (12)0.3220 (5)0.08753 (10)0.0421 (12)
N20.9205 (10)0.4713 (4)0.10536 (8)0.0506 (11)
C130.6562 (12)0.0364 (5)0.05006 (10)0.0431 (11)
C41.0942 (12)0.5998 (5)0.15664 (10)0.0433 (12)
C110.8984 (13)0.3162 (5)0.05408 (9)0.0482 (12)
H11A1.00360.40830.04400.058*
C120.8172 (13)0.1730 (5)0.03578 (10)0.0505 (13)
H12A0.87230.16890.01350.061*
C31.2227 (13)0.5869 (5)0.18867 (9)0.0455 (12)
C90.6573 (12)0.1861 (5)0.10172 (10)0.0438 (12)
H9A0.60330.18990.12410.053*
O21.4501 (11)0.3130 (4)0.18665 (8)0.0813 (13)
C80.5695 (12)0.0423 (5)0.08302 (10)0.0471 (13)
H8A0.45430.04770.09270.056*
N11.2977 (13)0.4173 (5)0.20309 (10)0.0623 (12)
C61.1071 (14)0.9039 (5)0.16521 (12)0.0654 (16)
H6A1.07071.01300.15690.078*
C71.0088 (11)0.4530 (5)0.13540 (10)0.0460 (12)
H7A1.01990.34360.14420.055*
C51.0397 (13)0.7655 (5)0.14548 (10)0.0546 (14)
H5A0.95600.78280.12430.065*
C140.4282 (15)0.2451 (5)0.04323 (11)0.0698 (16)
H14A0.39410.32870.02620.105*
H14B0.57010.29180.06010.105*
H14C0.21670.21430.05270.105*
C21.2840 (15)0.7234 (6)0.20893 (11)0.0627 (16)
H2B1.36240.70740.23030.075*
O11.2071 (14)0.3908 (5)0.23092 (9)0.1181 (19)
C11.2268 (16)0.8852 (6)0.19681 (12)0.0712 (17)
H1A1.26890.98040.20990.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.069 (2)0.0526 (16)0.0587 (19)0.010 (2)0.0010 (19)0.0113 (16)
C100.040 (3)0.040 (2)0.047 (3)0.006 (3)0.006 (3)0.001 (2)
N20.054 (3)0.052 (2)0.046 (2)0.002 (2)0.007 (2)0.0026 (18)
C130.043 (3)0.042 (2)0.045 (3)0.002 (3)0.007 (3)0.000 (2)
C40.043 (3)0.048 (2)0.039 (2)0.002 (3)0.003 (2)0.003 (2)
C110.054 (3)0.046 (2)0.044 (3)0.004 (3)0.006 (3)0.009 (2)
C120.056 (4)0.058 (3)0.037 (2)0.001 (3)0.001 (3)0.007 (2)
C30.053 (3)0.044 (2)0.040 (2)0.003 (3)0.001 (2)0.004 (2)
C90.041 (3)0.053 (2)0.038 (2)0.003 (3)0.007 (2)0.001 (2)
O20.103 (4)0.064 (2)0.078 (2)0.020 (3)0.007 (3)0.0003 (19)
C80.048 (3)0.048 (3)0.045 (3)0.001 (3)0.001 (3)0.006 (2)
N10.077 (3)0.067 (3)0.043 (2)0.003 (3)0.003 (3)0.002 (2)
C60.079 (4)0.045 (3)0.072 (3)0.000 (3)0.007 (3)0.001 (3)
C70.037 (3)0.045 (3)0.056 (3)0.001 (2)0.000 (3)0.000 (2)
C50.060 (4)0.050 (3)0.054 (3)0.001 (3)0.007 (3)0.000 (2)
C140.073 (4)0.055 (3)0.081 (3)0.010 (4)0.019 (3)0.014 (3)
C20.078 (4)0.064 (3)0.047 (3)0.014 (3)0.005 (3)0.005 (2)
O10.181 (5)0.108 (3)0.065 (2)0.024 (4)0.010 (3)0.029 (2)
C10.089 (4)0.061 (3)0.064 (3)0.012 (4)0.010 (4)0.017 (3)
Geometric parameters (Å, º) top
O3—C131.367 (4)C9—C81.402 (5)
O3—C141.444 (5)C9—H9A0.9300
C10—C91.379 (5)O2—N11.217 (5)
C10—C111.387 (5)C8—H8A0.9300
C10—N21.430 (5)N1—O11.201 (5)
N2—C71.274 (5)C6—C11.373 (6)
C13—C121.376 (5)C6—C51.373 (5)
C13—C81.379 (5)C6—H6A0.9300
C4—C51.393 (5)C7—H7A0.9300
C4—C31.398 (5)C5—H5A0.9300
C4—C71.477 (5)C14—H14A0.9600
C11—C121.384 (5)C14—H14B0.9600
C11—H11A0.9300C14—H14C0.9600
C12—H12A0.9300C2—C11.378 (6)
C3—C21.370 (5)C2—H2B0.9300
C3—N11.482 (5)C1—H1A0.9300
C13—O3—C14117.6 (3)C9—C8—H8A120.5
C9—C10—C11119.0 (4)O1—N1—O2123.2 (5)
C9—C10—N2123.7 (4)O1—N1—C3117.5 (4)
C11—C10—N2117.3 (4)O2—N1—C3119.3 (4)
C7—N2—C10117.7 (3)C1—C6—C5121.7 (4)
O3—C13—C12115.4 (4)C1—C6—H6A119.2
O3—C13—C8124.7 (4)C5—C6—H6A119.2
C12—C13—C8119.8 (4)N2—C7—C4122.1 (4)
C5—C4—C3115.2 (4)N2—C7—H7A119.0
C5—C4—C7120.2 (4)C4—C7—H7A119.0
C3—C4—C7124.6 (4)C6—C5—C4121.2 (4)
C12—C11—C10119.8 (4)C6—C5—H5A119.4
C12—C11—H11A120.1C4—C5—H5A119.4
C10—C11—H11A120.1O3—C14—H14A109.5
C13—C12—C11121.1 (4)O3—C14—H14B109.5
C13—C12—H12A119.4H14A—C14—H14B109.5
C11—C12—H12A119.4O3—C14—H14C109.5
C2—C3—C4124.3 (4)H14A—C14—H14C109.5
C2—C3—N1115.4 (4)H14B—C14—H14C109.5
C4—C3—N1120.3 (4)C3—C2—C1118.5 (4)
C10—C9—C8121.1 (4)C3—C2—H2B120.8
C10—C9—H9A119.4C1—C2—H2B120.8
C8—C9—H9A119.4C6—C1—C2119.2 (5)
C13—C8—C9119.1 (4)C6—C1—H1A120.4
C13—C8—H8A120.5C2—C1—H1A120.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O3i0.962.633.469 (5)146
Symmetry code: (i) x1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC14H12N2O3
Mr256.26
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)4.0010 (8), 7.8410 (16), 40.447 (8)
V3)1268.9 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.20 × 0.15 × 0.11
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3103, 1651, 748
Rint0.087
(sin θ/λ)max1)0.638
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.135, 0.96
No. of reflections1651
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C14—H14A···O3i0.962.633.469 (5)146.3
Symmetry code: (i) x1/2, y+1/2, z.
 

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDeschamps, P., Kulkarni, P. P. & Sarkar, B. (2003). Inorg. Chem. 42, 7366–7368.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationJian, 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
First citationRozwadowski, Z., Majewski, E., Dziembowska, T. & Hansen, P. E. (1999). Chem. Soc. Perkin Trans. 2, pp. 2809–2817.  Web of Science CrossRef Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTarafder, 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

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