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Acta Cryst. (2009). E65, o669    [ doi:10.1107/S1600536809007107 ]

(E)-N-[(5-Methyl-2-furyl)methylene]-3-nitroaniline

Y.-N. Guo

Abstract top

The asymmetric unit of the title compound, C12H10N2O3, contains two crystallographically independent molecules, in which the furan and benzene rings are oriented at dihedral angles of 46.09 (3) and 39.98 (3)°. In the crystal structure, weak intermolecular C-H...N hydrogen bonds link the molecules into chains running nearly parallel to the a axis.

Comment top

Schiff base complexes are of great interests for inorganic and bioinorganic chemists. To the best of our knowledge, in the past two decades, Schiff base complexes derived from furaldehydes have been less reported (Li & Zhang, 2005). Furaldehydes are raw materials used for preparing many medicines and industrial products, and some of furfural derivatives have a strong bactericidal ability and their antibacterial activities are fairly broad (Antal et al., 1991; Basta & EI-Saied, 2003). As an extension of our work on the structural characterizations of Schiff bases of furaldehyde derivatives, we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. Rings A (O1/C2-C5), B (C7-C12) and C (O4/C14-C17), D (C19-C24) are, of course, planar, and they are oriented at dihedral angles of A/B = 46.09 (3) and C/D = 39.98 (3) °.

In the crystal structure, weak intermolecular C-H···N hydrogen bonds (Table 1) link the molecules into chains nearly parallel to the a-axis (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Li & Zhang (2005); Antal et al. (1991); Basta & EI-Saied (2003). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 5-methyl-2-furaldehyde (11.0 mg, 0.1 mmol) and 3-nitrobenzenamine (13.8 mg, 0.1 mmol) were dissolved in methanol (10 ml). The mixture was stirred for 1 h at room temperature, and then filtered. After allowing the filtrate to stand in air for 7 d, yellow block-shaped crystals of the title compound were obtained. They were collected, washed with methanol and dried in a vacuum desiccator using anhydrous CaCl2 (yield; 60%).

Refinement top

H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.2 for aromatic H and x = 1.5 for methyl H atoms. Friedel pairs were merged.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding are omitted.
(E)-N-[(5-Methyl-2-furyl)methylene]-3-nitroaniline top
Crystal data top
C12H10N2O3F(000) = 960
Mr = 230.22Dx = 1.385 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 1515 reflections
a = 21.634 (2) Åθ = 2.4–20.5°
b = 3.8286 (9) ŵ = 0.10 mm−1
c = 26.660 (2) ÅT = 298 K
V = 2208.2 (6) Å3Block, yellow
Z = 80.42 × 0.39 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		2002 independent reflections
Radiation source: fine-focus sealed tube1331 reflections with I > 2σ(I)
graphiteRint = 0.051
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Siemens, 1996)		h = −25→24
Tmin = 0.959, Tmax = 0.980k = −4→4
8789 measured reflectionsl = −31→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0216P)2 + 0.7218P]
where P = (Fo2 + 2Fc2)/3
2002 reflections(Δ/σ)max < 0.001
307 parametersΔρmax = 0.15 e Å−3
1 restraintΔρmin = −0.15 e Å−3
Crystal data top
C12H10N2O3V = 2208.2 (6) Å3
Mr = 230.22Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 21.634 (2) ŵ = 0.10 mm−1
b = 3.8286 (9) ÅT = 298 K
c = 26.660 (2) Å0.42 × 0.39 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		2002 independent reflections
Absorption correction: multi-scan
(SADABS; Siemens, 1996)		1331 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.980Rint = 0.051
8789 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.127Δρmax = 0.15 e Å−3
S = 1.06Δρmin = −0.15 e Å−3
2002 reflectionsAbsolute structure: ?
307 parametersFlack parameter: ?
1 restraintRogers parameter: ?
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
N10.06199 (19)0.3004 (10)0.26104 (17)0.0472 (11)
N20.0529 (3)0.1073 (14)0.4392 (2)0.0681 (14)
N30.31807 (19)0.9617 (11)0.36859 (16)0.0470 (11)
N40.2860 (3)1.0358 (15)0.19047 (19)0.0657 (14)
O10.00925 (16)0.2744 (9)0.16401 (13)0.0497 (9)
O20.0034 (2)−0.0350 (15)0.43257 (19)0.0921 (16)
O30.0753 (3)0.1515 (18)0.48052 (16)0.110 (2)
O40.27482 (18)0.7909 (9)0.46480 (13)0.0520 (10)
O50.2380 (2)0.8701 (14)0.19661 (19)0.0890 (16)
O60.3026 (3)1.1466 (17)0.14984 (17)0.1053 (19)
C10.0915 (2)0.1827 (14)0.2234 (2)0.0466 (13)
H10.13200.10960.22870.056*
C20.0677 (2)0.1540 (14)0.17390 (19)0.0460 (13)
C30.0929 (3)0.0267 (15)0.1313 (2)0.0586 (16)
H30.1321−0.06990.12770.070*
C40.0488 (3)0.0683 (15)0.0937 (2)0.0611 (16)
H40.05330.00520.06020.073*
C5−0.0012 (3)0.2153 (14)0.1144 (2)0.0526 (15)
C6−0.0618 (3)0.3237 (16)0.0943 (2)0.0646 (17)
H6A−0.06310.27830.05890.097*
H6B−0.06770.56880.10010.097*
H6C−0.09400.19440.11070.097*
C70.0929 (2)0.3138 (12)0.3078 (2)0.0409 (12)
C80.0596 (2)0.2124 (14)0.3490 (2)0.0447 (13)
H80.01890.13850.34590.054*
C90.0879 (3)0.2223 (15)0.39510 (19)0.0494 (14)
C100.1472 (3)0.3357 (16)0.4017 (2)0.0592 (15)
H100.16530.33910.43340.071*
C110.1794 (3)0.4448 (15)0.3600 (2)0.0609 (16)
H110.21960.52800.36350.073*
C120.1525 (2)0.4314 (13)0.3136 (2)0.0499 (14)
H120.17490.50260.28560.060*
C130.3537 (3)0.8338 (15)0.4012 (2)0.0511 (14)
H130.39510.80580.39290.061*
C140.3343 (3)0.7292 (14)0.4502 (2)0.0490 (13)
C150.3657 (3)0.5765 (16)0.4878 (2)0.0621 (16)
H150.40700.51010.48730.075*
C160.3243 (3)0.5366 (16)0.5277 (2)0.0672 (18)
H160.33290.43640.55870.081*
C170.2701 (3)0.6692 (14)0.5130 (2)0.0569 (16)
C180.2091 (3)0.7113 (18)0.5369 (2)0.078 (2)
H18A0.20170.95430.54340.117*
H18B0.20820.58410.56790.117*
H18C0.17760.62290.51490.117*
C190.3425 (2)1.0521 (13)0.32122 (18)0.0421 (12)
C200.3048 (2)1.0067 (12)0.27975 (19)0.0422 (12)
H200.26510.91720.28360.051*
C210.3259 (3)1.0933 (14)0.23347 (19)0.0484 (13)
C220.3846 (3)1.2301 (14)0.2259 (2)0.0589 (16)
H220.39841.28410.19370.071*
C230.4218 (3)1.2838 (15)0.2669 (3)0.0568 (15)
H230.46111.37800.26290.068*
C240.4007 (2)1.1980 (13)0.3141 (2)0.0542 (14)
H240.42591.23830.34170.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.040 (2)0.046 (3)0.055 (3)0.002 (2)0.007 (2)0.003 (2)
N20.060 (4)0.085 (4)0.059 (4)0.005 (3)0.004 (3)0.008 (3)
N30.047 (3)0.047 (3)0.047 (3)0.000 (2)−0.002 (2)−0.003 (2)
N40.065 (4)0.083 (4)0.048 (3)0.019 (3)0.004 (3)−0.002 (3)
O10.050 (2)0.050 (2)0.049 (2)0.0024 (17)0.0033 (17)−0.0044 (17)
O20.060 (3)0.141 (5)0.076 (3)−0.015 (3)0.015 (2)0.016 (3)
O30.116 (4)0.164 (6)0.052 (3)−0.029 (4)−0.012 (3)0.018 (3)
O40.059 (3)0.053 (2)0.044 (2)0.0019 (18)−0.0083 (17)0.0021 (18)
O50.063 (3)0.132 (5)0.072 (3)−0.004 (3)−0.013 (2)−0.014 (3)
O60.128 (5)0.140 (5)0.048 (3)0.002 (4)0.006 (3)0.007 (3)
C10.033 (3)0.050 (3)0.057 (4)−0.001 (2)0.006 (3)0.006 (3)
C20.044 (3)0.048 (3)0.047 (3)0.003 (2)0.006 (3)0.001 (2)
C30.058 (4)0.055 (4)0.062 (4)0.003 (3)0.014 (3)−0.002 (3)
C40.075 (4)0.058 (4)0.050 (3)−0.007 (3)0.014 (3)−0.010 (3)
C50.063 (4)0.048 (3)0.047 (4)−0.009 (3)0.003 (3)−0.004 (3)
C60.076 (5)0.062 (4)0.055 (4)0.000 (3)−0.007 (3)−0.002 (3)
C70.036 (3)0.035 (3)0.051 (3)0.004 (2)−0.002 (3)−0.003 (2)
C80.034 (3)0.045 (3)0.055 (3)0.002 (2)−0.001 (3)−0.002 (3)
C90.049 (3)0.052 (4)0.046 (3)0.002 (3)0.002 (3)0.002 (3)
C100.054 (4)0.064 (4)0.060 (4)0.002 (3)−0.016 (3)−0.005 (3)
C110.040 (3)0.061 (4)0.082 (5)−0.010 (3)−0.009 (3)−0.002 (3)
C120.041 (3)0.042 (3)0.067 (4)−0.006 (2)0.005 (3)0.007 (3)
C130.051 (4)0.050 (3)0.052 (4)−0.002 (3)−0.007 (3)−0.007 (3)
C140.051 (3)0.043 (3)0.052 (3)0.003 (3)−0.007 (3)−0.008 (3)
C150.066 (4)0.053 (4)0.067 (4)−0.001 (3)−0.025 (3)−0.004 (3)
C160.097 (5)0.060 (4)0.045 (4)−0.002 (4)−0.020 (4)0.002 (3)
C170.087 (5)0.044 (3)0.040 (3)−0.009 (3)−0.003 (3)−0.003 (3)
C180.097 (5)0.072 (5)0.064 (4)−0.011 (4)0.016 (4)0.000 (3)
C190.041 (3)0.039 (3)0.046 (3)−0.004 (2)0.007 (2)−0.001 (2)
C200.033 (3)0.043 (3)0.051 (3)0.000 (2)0.005 (2)−0.002 (3)
C210.053 (3)0.044 (3)0.048 (3)0.007 (3)0.007 (3)0.002 (3)
C220.062 (4)0.044 (3)0.071 (4)0.002 (3)0.027 (4)0.010 (3)
C230.039 (3)0.049 (4)0.083 (4)−0.008 (2)0.014 (3)0.000 (3)
C240.046 (3)0.044 (3)0.073 (4)0.000 (2)0.002 (3)−0.010 (3)
Geometric parameters (Å, °) top
N1—C11.273 (6)C8—H80.9300
N1—C71.415 (6)C9—C101.366 (7)
N2—O21.215 (7)C10—C111.376 (8)
N2—O31.216 (6)C10—H100.9300
N2—C91.465 (7)C11—C121.369 (8)
N3—C131.260 (6)C11—H110.9300
N3—C191.412 (6)C12—H120.9300
N4—O61.218 (7)C13—C141.429 (8)
N4—O51.229 (6)C13—H130.9300
N4—C211.452 (7)C14—C151.345 (8)
O1—C51.359 (6)C15—C161.400 (9)
O1—C21.371 (6)C15—H150.9300
O4—C141.364 (7)C16—C171.335 (8)
O4—C171.372 (6)C16—H160.9300
C1—C21.420 (7)C17—C181.474 (9)
C1—H10.9300C18—H18A0.9600
C2—C31.352 (7)C18—H18B0.9600
C3—C41.393 (9)C18—H18C0.9600
C3—H30.9300C19—C201.385 (7)
C4—C51.339 (8)C19—C241.391 (7)
C4—H40.9300C20—C211.357 (7)
C5—C61.477 (8)C20—H200.9300
C6—H6A0.9600C21—C221.387 (8)
C6—H6B0.9600C22—C231.375 (8)
C6—H6C0.9600C22—H220.9300
C7—C81.370 (7)C23—C241.377 (8)
C7—C121.375 (6)C23—H230.9300
C8—C91.372 (7)C24—H240.9300
C1—N1—C7118.1 (4)C12—C11—H11119.9
O2—N2—O3123.1 (6)C10—C11—H11119.9
O2—N2—C9118.3 (5)C11—C12—C7120.9 (5)
O3—N2—C9118.7 (6)C11—C12—H12119.6
C13—N3—C19118.9 (5)C7—C12—H12119.6
O6—N4—O5123.2 (6)N3—C13—C14124.0 (5)
O6—N4—C21118.3 (6)N3—C13—H13118.0
O5—N4—C21118.4 (5)C14—C13—H13118.0
C5—O1—C2106.5 (4)C15—C14—O4109.8 (5)
C14—O4—C17106.2 (4)C15—C14—C13130.9 (6)
N1—C1—C2125.3 (5)O4—C14—C13119.3 (5)
N1—C1—H1117.4C14—C15—C16106.9 (6)
C2—C1—H1117.4C14—C15—H15126.6
C3—C2—O1109.4 (5)C16—C15—H15126.6
C3—C2—C1131.5 (5)C17—C16—C15107.3 (5)
O1—C2—C1119.2 (4)C17—C16—H16126.3
C2—C3—C4106.7 (5)C15—C16—H16126.3
C2—C3—H3126.6C16—C17—O4109.8 (5)
C4—C3—H3126.6C16—C17—C18134.5 (6)
C5—C4—C3107.7 (5)O4—C17—C18115.7 (6)
C5—C4—H4126.2C17—C18—H18A109.5
C3—C4—H4126.2C17—C18—H18B109.5
C4—C5—O1109.7 (5)H18A—C18—H18B109.5
C4—C5—C6133.2 (6)C17—C18—H18C109.5
O1—C5—C6117.1 (5)H18A—C18—H18C109.5
C5—C6—H6A109.5H18B—C18—H18C109.5
C5—C6—H6B109.5C20—C19—C24118.3 (5)
H6A—C6—H6B109.5C20—C19—N3117.6 (4)
C5—C6—H6C109.5C24—C19—N3124.0 (5)
H6A—C6—H6C109.5C21—C20—C19119.8 (5)
H6B—C6—H6C109.5C21—C20—H20120.1
C8—C7—C12119.6 (5)C19—C20—H20120.1
C8—C7—N1116.7 (4)C20—C21—C22122.2 (5)
C12—C7—N1123.7 (5)C20—C21—N4118.7 (5)
C7—C8—C9118.5 (5)C22—C21—N4119.1 (5)
C7—C8—H8120.8C23—C22—C21118.4 (5)
C9—C8—H8120.8C23—C22—H22120.8
C10—C9—C8122.8 (5)C21—C22—H22120.8
C10—C9—N2118.5 (5)C22—C23—C24119.9 (5)
C8—C9—N2118.7 (5)C22—C23—H23120.1
C9—C10—C11117.9 (5)C24—C23—H23120.1
C9—C10—H10121.0C23—C24—C19121.4 (5)
C11—C10—H10121.0C23—C24—H24119.3
C12—C11—C10120.2 (5)C19—C24—H24119.3
C7—N1—C1—C2−179.5 (5)C19—N3—C13—C14−179.4 (5)
C5—O1—C2—C30.6 (6)C17—O4—C14—C15−0.3 (6)
C5—O1—C2—C1179.8 (5)C17—O4—C14—C13−179.1 (5)
N1—C1—C2—C3−177.9 (6)N3—C13—C14—C15176.7 (6)
N1—C1—C2—O13.1 (8)N3—C13—C14—O4−4.8 (8)
O1—C2—C3—C4−0.1 (6)O4—C14—C15—C160.6 (7)
C1—C2—C3—C4−179.2 (6)C13—C14—C15—C16179.2 (5)
C2—C3—C4—C5−0.4 (7)C14—C15—C16—C17−0.7 (7)
C3—C4—C5—O10.7 (6)C15—C16—C17—O40.5 (7)
C3—C4—C5—C6179.7 (6)C15—C16—C17—C18−179.2 (6)
C2—O1—C5—C4−0.8 (6)C14—O4—C17—C16−0.2 (6)
C2—O1—C5—C6−180.0 (5)C14—O4—C17—C18179.6 (5)
C1—N1—C7—C8−137.9 (5)C13—N3—C19—C20145.3 (5)
C1—N1—C7—C1244.1 (7)C13—N3—C19—C24−37.8 (7)
C12—C7—C8—C9−1.8 (7)C24—C19—C20—C212.2 (7)
N1—C7—C8—C9−179.9 (4)N3—C19—C20—C21179.3 (5)
C7—C8—C9—C101.4 (8)C19—C20—C21—C22−0.5 (8)
C7—C8—C9—N2−178.8 (5)C19—C20—C21—N4178.6 (5)
O2—N2—C9—C10−170.6 (6)O6—N4—C21—C20172.6 (6)
O3—N2—C9—C107.8 (9)O5—N4—C21—C20−9.2 (8)
O2—N2—C9—C89.5 (8)O6—N4—C21—C22−8.3 (8)
O3—N2—C9—C8−172.1 (6)O5—N4—C21—C22169.9 (5)
C8—C9—C10—C110.2 (9)C20—C21—C22—C23−1.1 (8)
N2—C9—C10—C11−179.7 (5)N4—C21—C22—C23179.9 (5)
C9—C10—C11—C12−1.3 (9)C21—C22—C23—C240.8 (8)
C10—C11—C12—C70.9 (8)C22—C23—C24—C190.9 (8)
C8—C7—C12—C110.7 (8)C20—C19—C24—C23−2.4 (8)
N1—C7—C12—C11178.6 (5)N3—C19—C24—C23−179.4 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C23—H23···N1i0.932.513.429 (3)172
Symmetry codes: (i) x+1/2, −y+2, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C23—H23···N1i0.932.513.429 (3)172
Symmetry codes: (i) x+1/2, −y+2, z.
Acknowledgements top

The author gratefully acknowledges support from a research project (grant No. 05jk136) of the Education Department of Shaanxi Province.

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Antal, M. J. Jr, Leesomboon, T., Mok, W. S. & Richards, G. N. (1991). Carbohydr. Res. 17, 71–85.

Basta, A. H. & EI-Saied, H. (2003). Cellul. Chem. Technol. 37, 79–94.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Li, Z. X. & Zhang, X. L. (2005). Chin. J. Struct. Chem. 24, 1310–1313.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.