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

Guo, Y.-N.

doi:10.1107/S1600536809007107

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o669

doi:10.1107/S1600536809007107

Open

access

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

Ya-Ning Guo ^a ^*

^aDepartment of Chemistry, Baoji University of Arts and Sciences, Baoji, Shaanxi 721007, People's Republic of China
^*Correspondence e-mail: ggyn1997@163.com

(Received 21 February 2009; accepted 26 February 2009; online 6 March 2009)

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.

Related literature

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

Experimental

Crystal data

C₁₂H₁₀N₂O₃
M_r = 230.22
Orthorhombic, P c a 2₁
a = 21.634 (2) Å
b = 3.8286 (9) Å
c = 26.660 (2) Å
V = 2208.2 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.42 × 0.39 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ) T_min = 0.959, T_max = 0.980
8789 measured reflections
2002 independent reflections
1331 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.127
S = 1.06
2002 reflections
307 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯N1ⁱ	0.93	2.51	3.429 (3)	172
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+2, z]$ .

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007107/hk2629sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007107/hk2629Isup2.hkl

checkCIF report

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%).

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

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

C₁₂H₁₀N₂O₃	F(000) = 960
M_r = 230.22	D_x = 1.385 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1515 reflections
a = 21.634 (2) Å	θ = 2.4–20.5°
b = 3.8286 (9) Å	µ = 0.10 mm⁻¹
c = 26.660 (2) Å	T = 298 K
V = 2208.2 (6) Å³	Block, yellow
Z = 8	0.42 × 0.39 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2002 independent reflections
Radiation source: fine-focus sealed tube	1331 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −25→24
T_min = 0.959, T_max = 0.980	k = −4→4
8789 measured reflections	l = −31→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0216P)² + 0.7218P] where P = (F_o² + 2F_c²)/3
2002 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₂H₁₀N₂O₃	V = 2208.2 (6) Å³
M_r = 230.22	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 21.634 (2) Å	µ = 0.10 mm⁻¹
b = 3.8286 (9) Å	T = 298 K
c = 26.660 (2) Å	0.42 × 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)
T_min = 0.959, T_max = 0.980	R_int = 0.051
8789 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.127	H-atom parameters constrained
S = 1.06	Δρ_max = 0.15 e Å⁻³
2002 reflections	Δρ_min = −0.16 e Å⁻³
307 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
N1	0.06199 (19)	0.3004 (10)	0.26104 (17)	0.0472 (11)
N2	0.0529 (3)	0.1073 (14)	0.4392 (2)	0.0681 (14)
N3	0.31807 (19)	0.9617 (11)	0.36859 (16)	0.0470 (11)
N4	0.2860 (3)	1.0358 (15)	0.19047 (19)	0.0657 (14)
O1	0.00925 (16)	0.2744 (9)	0.16401 (13)	0.0497 (9)
O2	0.0034 (2)	−0.0350 (15)	0.43257 (19)	0.0921 (16)
O3	0.0753 (3)	0.1515 (18)	0.48052 (16)	0.110 (2)
O4	0.27482 (18)	0.7909 (9)	0.46480 (13)	0.0520 (10)
O5	0.2380 (2)	0.8701 (14)	0.19661 (19)	0.0890 (16)
O6	0.3026 (3)	1.1466 (17)	0.14984 (17)	0.1053 (19)
C1	0.0915 (2)	0.1827 (14)	0.2234 (2)	0.0466 (13)
H1	0.1320	0.1096	0.2287	0.056*
C2	0.0677 (2)	0.1540 (14)	0.17390 (19)	0.0460 (13)
C3	0.0929 (3)	0.0267 (15)	0.1313 (2)	0.0586 (16)
H3	0.1321	−0.0699	0.1277	0.070*
C4	0.0488 (3)	0.0683 (15)	0.0937 (2)	0.0611 (16)
H4	0.0533	0.0052	0.0602	0.073*
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	−0.0631	0.2783	0.0589	0.097*
H6B	−0.0677	0.5688	0.1001	0.097*
H6C	−0.0940	0.1944	0.1107	0.097*
C7	0.0929 (2)	0.3138 (12)	0.3078 (2)	0.0409 (12)
C8	0.0596 (2)	0.2124 (14)	0.3490 (2)	0.0447 (13)
H8	0.0189	0.1385	0.3459	0.054*
C9	0.0879 (3)	0.2223 (15)	0.39510 (19)	0.0494 (14)
C10	0.1472 (3)	0.3357 (16)	0.4017 (2)	0.0592 (15)
H10	0.1653	0.3391	0.4334	0.071*
C11	0.1794 (3)	0.4448 (15)	0.3600 (2)	0.0609 (16)
H11	0.2196	0.5280	0.3635	0.073*
C12	0.1525 (2)	0.4314 (13)	0.3136 (2)	0.0499 (14)
H12	0.1749	0.5026	0.2856	0.060*
C13	0.3537 (3)	0.8338 (15)	0.4012 (2)	0.0511 (14)
H13	0.3951	0.8058	0.3929	0.061*
C14	0.3343 (3)	0.7292 (14)	0.4502 (2)	0.0490 (13)
C15	0.3657 (3)	0.5765 (16)	0.4878 (2)	0.0621 (16)
H15	0.4070	0.5101	0.4873	0.075*
C16	0.3243 (3)	0.5366 (16)	0.5277 (2)	0.0672 (18)
H16	0.3329	0.4364	0.5587	0.081*
C17	0.2701 (3)	0.6692 (14)	0.5130 (2)	0.0569 (16)
C18	0.2091 (3)	0.7113 (18)	0.5369 (2)	0.078 (2)
H18A	0.2017	0.9543	0.5434	0.117*
H18B	0.2082	0.5841	0.5679	0.117*
H18C	0.1776	0.6229	0.5149	0.117*
C19	0.3425 (2)	1.0521 (13)	0.32122 (18)	0.0421 (12)
C20	0.3048 (2)	1.0067 (12)	0.27975 (19)	0.0422 (12)
H20	0.2651	0.9172	0.2836	0.051*
C21	0.3259 (3)	1.0933 (14)	0.23347 (19)	0.0484 (13)
C22	0.3846 (3)	1.2301 (14)	0.2259 (2)	0.0589 (16)
H22	0.3984	1.2841	0.1937	0.071*
C23	0.4218 (3)	1.2838 (15)	0.2669 (3)	0.0568 (15)
H23	0.4611	1.3780	0.2629	0.068*
C24	0.4007 (2)	1.1980 (13)	0.3141 (2)	0.0542 (14)
H24	0.4259	1.2383	0.3417	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.040 (2)	0.046 (3)	0.055 (3)	0.002 (2)	0.007 (2)	0.003 (2)
N2	0.060 (4)	0.085 (4)	0.059 (4)	0.005 (3)	0.004 (3)	0.008 (3)
N3	0.047 (3)	0.047 (3)	0.047 (3)	0.000 (2)	−0.002 (2)	−0.003 (2)
N4	0.065 (4)	0.083 (4)	0.048 (3)	0.019 (3)	0.004 (3)	−0.002 (3)
O1	0.050 (2)	0.050 (2)	0.049 (2)	0.0024 (17)	0.0033 (17)	−0.0044 (17)
O2	0.060 (3)	0.141 (5)	0.076 (3)	−0.015 (3)	0.015 (2)	0.016 (3)
O3	0.116 (4)	0.164 (6)	0.052 (3)	−0.029 (4)	−0.012 (3)	0.018 (3)
O4	0.059 (3)	0.053 (2)	0.044 (2)	0.0019 (18)	−0.0083 (17)	0.0021 (18)
O5	0.063 (3)	0.132 (5)	0.072 (3)	−0.004 (3)	−0.013 (2)	−0.014 (3)
O6	0.128 (5)	0.140 (5)	0.048 (3)	0.002 (4)	0.006 (3)	0.007 (3)
C1	0.033 (3)	0.050 (3)	0.057 (4)	−0.001 (2)	0.006 (3)	0.006 (3)
C2	0.044 (3)	0.048 (3)	0.047 (3)	0.003 (2)	0.006 (3)	0.001 (2)
C3	0.058 (4)	0.055 (4)	0.062 (4)	0.003 (3)	0.014 (3)	−0.002 (3)
C4	0.075 (4)	0.058 (4)	0.050 (3)	−0.007 (3)	0.014 (3)	−0.010 (3)
C5	0.063 (4)	0.048 (3)	0.047 (4)	−0.009 (3)	0.003 (3)	−0.004 (3)
C6	0.076 (5)	0.062 (4)	0.055 (4)	0.000 (3)	−0.007 (3)	−0.002 (3)
C7	0.036 (3)	0.035 (3)	0.051 (3)	0.004 (2)	−0.002 (3)	−0.003 (2)
C8	0.034 (3)	0.045 (3)	0.055 (3)	0.002 (2)	−0.001 (3)	−0.002 (3)
C9	0.049 (3)	0.052 (4)	0.046 (3)	0.002 (3)	0.002 (3)	0.002 (3)
C10	0.054 (4)	0.064 (4)	0.060 (4)	0.002 (3)	−0.016 (3)	−0.005 (3)
C11	0.040 (3)	0.061 (4)	0.082 (5)	−0.010 (3)	−0.009 (3)	−0.002 (3)
C12	0.041 (3)	0.042 (3)	0.067 (4)	−0.006 (2)	0.005 (3)	0.007 (3)
C13	0.051 (4)	0.050 (3)	0.052 (4)	−0.002 (3)	−0.007 (3)	−0.007 (3)
C14	0.051 (3)	0.043 (3)	0.052 (3)	0.003 (3)	−0.007 (3)	−0.008 (3)
C15	0.066 (4)	0.053 (4)	0.067 (4)	−0.001 (3)	−0.025 (3)	−0.004 (3)
C16	0.097 (5)	0.060 (4)	0.045 (4)	−0.002 (4)	−0.020 (4)	0.002 (3)
C17	0.087 (5)	0.044 (3)	0.040 (3)	−0.009 (3)	−0.003 (3)	−0.003 (3)
C18	0.097 (5)	0.072 (5)	0.064 (4)	−0.011 (4)	0.016 (4)	0.000 (3)
C19	0.041 (3)	0.039 (3)	0.046 (3)	−0.004 (2)	0.007 (2)	−0.001 (2)
C20	0.033 (3)	0.043 (3)	0.051 (3)	0.000 (2)	0.005 (2)	−0.002 (3)
C21	0.053 (3)	0.044 (3)	0.048 (3)	0.007 (3)	0.007 (3)	0.002 (3)
C22	0.062 (4)	0.044 (3)	0.071 (4)	0.002 (3)	0.027 (4)	0.010 (3)
C23	0.039 (3)	0.049 (4)	0.083 (4)	−0.008 (2)	0.014 (3)	0.000 (3)
C24	0.046 (3)	0.044 (3)	0.073 (4)	0.000 (2)	0.002 (3)	−0.010 (3)

Geometric parameters (Å, º) top

N1—C1	1.273 (6)	C8—H8	0.9300
N1—C7	1.415 (6)	C9—C10	1.366 (7)
N2—O2	1.215 (7)	C10—C11	1.376 (8)
N2—O3	1.216 (6)	C10—H10	0.9300
N2—C9	1.465 (7)	C11—C12	1.369 (8)
N3—C13	1.260 (6)	C11—H11	0.9300
N3—C19	1.412 (6)	C12—H12	0.9300
N4—O6	1.218 (7)	C13—C14	1.429 (8)
N4—O5	1.229 (6)	C13—H13	0.9300
N4—C21	1.452 (7)	C14—C15	1.345 (8)
O1—C5	1.359 (6)	C15—C16	1.400 (9)
O1—C2	1.371 (6)	C15—H15	0.9300
O4—C14	1.364 (7)	C16—C17	1.335 (8)
O4—C17	1.372 (6)	C16—H16	0.9300
C1—C2	1.420 (7)	C17—C18	1.474 (9)
C1—H1	0.9300	C18—H18A	0.9600
C2—C3	1.352 (7)	C18—H18B	0.9600
C3—C4	1.393 (9)	C18—H18C	0.9600
C3—H3	0.9300	C19—C20	1.385 (7)
C4—C5	1.339 (8)	C19—C24	1.391 (7)
C4—H4	0.9300	C20—C21	1.357 (7)
C5—C6	1.477 (8)	C20—H20	0.9300
C6—H6A	0.9600	C21—C22	1.387 (8)
C6—H6B	0.9600	C22—C23	1.375 (8)
C6—H6C	0.9600	C22—H22	0.9300
C7—C8	1.370 (7)	C23—C24	1.377 (8)
C7—C12	1.375 (6)	C23—H23	0.9300
C8—C9	1.372 (7)	C24—H24	0.9300

C1—N1—C7	118.1 (4)	C12—C11—H11	119.9
O2—N2—O3	123.1 (6)	C10—C11—H11	119.9
O2—N2—C9	118.3 (5)	C11—C12—C7	120.9 (5)
O3—N2—C9	118.7 (6)	C11—C12—H12	119.6
C13—N3—C19	118.9 (5)	C7—C12—H12	119.6
O6—N4—O5	123.2 (6)	N3—C13—C14	124.0 (5)
O6—N4—C21	118.3 (6)	N3—C13—H13	118.0
O5—N4—C21	118.4 (5)	C14—C13—H13	118.0
C5—O1—C2	106.5 (4)	C15—C14—O4	109.8 (5)
C14—O4—C17	106.2 (4)	C15—C14—C13	130.9 (6)
N1—C1—C2	125.3 (5)	O4—C14—C13	119.3 (5)
N1—C1—H1	117.4	C14—C15—C16	106.9 (6)
C2—C1—H1	117.4	C14—C15—H15	126.6
C3—C2—O1	109.4 (5)	C16—C15—H15	126.6
C3—C2—C1	131.5 (5)	C17—C16—C15	107.3 (5)
O1—C2—C1	119.2 (4)	C17—C16—H16	126.3
C2—C3—C4	106.7 (5)	C15—C16—H16	126.3
C2—C3—H3	126.6	C16—C17—O4	109.8 (5)
C4—C3—H3	126.6	C16—C17—C18	134.5 (6)
C5—C4—C3	107.7 (5)	O4—C17—C18	115.7 (6)
C5—C4—H4	126.2	C17—C18—H18A	109.5
C3—C4—H4	126.2	C17—C18—H18B	109.5
C4—C5—O1	109.7 (5)	H18A—C18—H18B	109.5
C4—C5—C6	133.2 (6)	C17—C18—H18C	109.5
O1—C5—C6	117.1 (5)	H18A—C18—H18C	109.5
C5—C6—H6A	109.5	H18B—C18—H18C	109.5
C5—C6—H6B	109.5	C20—C19—C24	118.3 (5)
H6A—C6—H6B	109.5	C20—C19—N3	117.6 (4)
C5—C6—H6C	109.5	C24—C19—N3	124.0 (5)
H6A—C6—H6C	109.5	C21—C20—C19	119.8 (5)
H6B—C6—H6C	109.5	C21—C20—H20	120.1
C8—C7—C12	119.6 (5)	C19—C20—H20	120.1
C8—C7—N1	116.7 (4)	C20—C21—C22	122.2 (5)
C12—C7—N1	123.7 (5)	C20—C21—N4	118.7 (5)
C7—C8—C9	118.5 (5)	C22—C21—N4	119.1 (5)
C7—C8—H8	120.8	C23—C22—C21	118.4 (5)
C9—C8—H8	120.8	C23—C22—H22	120.8
C10—C9—C8	122.8 (5)	C21—C22—H22	120.8
C10—C9—N2	118.5 (5)	C22—C23—C24	119.9 (5)
C8—C9—N2	118.7 (5)	C22—C23—H23	120.1
C9—C10—C11	117.9 (5)	C24—C23—H23	120.1
C9—C10—H10	121.0	C23—C24—C19	121.4 (5)
C11—C10—H10	121.0	C23—C24—H24	119.3
C12—C11—C10	120.2 (5)	C19—C24—H24	119.3

C7—N1—C1—C2	−179.5 (5)	C19—N3—C13—C14	−179.4 (5)
C5—O1—C2—C3	0.6 (6)	C17—O4—C14—C15	−0.3 (6)
C5—O1—C2—C1	179.8 (5)	C17—O4—C14—C13	−179.1 (5)
N1—C1—C2—C3	−177.9 (6)	N3—C13—C14—C15	176.7 (6)
N1—C1—C2—O1	3.1 (8)	N3—C13—C14—O4	−4.8 (8)
O1—C2—C3—C4	−0.1 (6)	O4—C14—C15—C16	0.6 (7)
C1—C2—C3—C4	−179.2 (6)	C13—C14—C15—C16	179.2 (5)
C2—C3—C4—C5	−0.4 (7)	C14—C15—C16—C17	−0.7 (7)
C3—C4—C5—O1	0.7 (6)	C15—C16—C17—O4	0.5 (7)
C3—C4—C5—C6	179.7 (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—C18	179.6 (5)
C1—N1—C7—C8	−137.9 (5)	C13—N3—C19—C20	145.3 (5)
C1—N1—C7—C12	44.1 (7)	C13—N3—C19—C24	−37.8 (7)
C12—C7—C8—C9	−1.8 (7)	C24—C19—C20—C21	2.2 (7)
N1—C7—C8—C9	−179.9 (4)	N3—C19—C20—C21	179.3 (5)
C7—C8—C9—C10	1.4 (8)	C19—C20—C21—C22	−0.5 (8)
C7—C8—C9—N2	−178.8 (5)	C19—C20—C21—N4	178.6 (5)
O2—N2—C9—C10	−170.6 (6)	O6—N4—C21—C20	172.6 (6)
O3—N2—C9—C10	7.8 (9)	O5—N4—C21—C20	−9.2 (8)
O2—N2—C9—C8	9.5 (8)	O6—N4—C21—C22	−8.3 (8)
O3—N2—C9—C8	−172.1 (6)	O5—N4—C21—C22	169.9 (5)
C8—C9—C10—C11	0.2 (9)	C20—C21—C22—C23	−1.1 (8)
N2—C9—C10—C11	−179.7 (5)	N4—C21—C22—C23	179.9 (5)
C9—C10—C11—C12	−1.3 (9)	C21—C22—C23—C24	0.8 (8)
C10—C11—C12—C7	0.9 (8)	C22—C23—C24—C19	0.9 (8)
C8—C7—C12—C11	0.7 (8)	C20—C19—C24—C23	−2.4 (8)
N1—C7—C12—C11	178.6 (5)	N3—C19—C24—C23	−179.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···N1ⁱ	0.93	2.51	3.429 (3)	172

Symmetry code: (i) x+1/2, −y+2, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₂O₃
M_r	230.22
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	298
a, b, c (Å)	21.634 (2), 3.8286 (9), 26.660 (2)
V (Å³)	2208.2 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.42 × 0.39 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.959, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	8789, 2002, 1331
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.127, 1.06
No. of reflections	2002
No. of parameters	307
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···N1ⁱ	0.93	2.51	3.429 (3)	172

Symmetry code: (i) x+1/2, −y+2, z.

Acknowledgements

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

References

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. CrossRef Web of Science Google Scholar
Antal, M. J. Jr, Leesomboon, T., Mok, W. S. & Richards, G. N. (1991). Carbohydr. Res. 17, 71–85. CrossRef Web of Science Google Scholar
Basta, A. H. & El-Saied, H. (2003). Cellul. Chem. Technol. 37, 79–94. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Li, Z. X. & Zhang, X. L. (2005). Chin. J. Struct. Chem. 24, 1310–1313. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar