1-Nitro-4-(2-nitro­prop-1-en­yl)benzene

Yang, J.-K.; Zheng, M.; Luo, S.-P.; Li, Z.-B.

doi:10.1107/S1600536810023676

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1781

doi:10.1107/S1600536810023676

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1-Nitro-4-(2-nitroprop-1-enyl)benzene

Jian-Ke Yang,^a Mei Zheng,^a Shu-Ping Luo ^b and Zhao-Bo Li ^b ^*

^aHangzhou Zhongmei Huadong Pharmaceutical Co. Ltd, Hangzhou, 310000, People's Republic of China, and ^bState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, People's Republic of China
^*Correspondence e-mail: boyzb@163.com

(Received 3 June 2010; accepted 18 June 2010; online 26 June 2010)

The asymmetric unit of the title compound, C₉H₈N₂O₄, contains two crystallographically independent molecules, both of which adopt an E configuration about the C=C bond. In the crystal, the molecules stack into columns along the c axis through π–π interactions, with centroid–centroid distances of 3.695 (3) and 3.804 (3) Å. The columns are further connected into a three-dimensional network by C—H⋯O hydrogen bonds.

Related literature

For background to the chemistry of nitroalkenes, see: Ballini & Petrini (2004 ); Berner et al. (2002 ); Ono (2001 ).

Experimental

Crystal data

C₉H₈N₂O₄
M_r = 208.17
Monoclinic, P 2₁ /c
a = 13.3621 (11) Å
b = 9.7648 (7) Å
c = 14.8835 (11) Å
β = 91.290 (2)°
V = 1941.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.38 × 0.29 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.947, T_max = 0.978
18620 measured reflections
4430 independent reflections
1883 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.168
S = 1.01
4430 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9B—H18⋯O4Aⁱ	0.93	2.55	3.386 (4)	149
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 2006 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536810023676/rz2463sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023676/rz2463Isup2.hkl

checkCIF report

Comment top

Nitroalkenes are important organic intermediates, since they can be converted to synthetically useful N– and O-containing organic molecules, such as amines, aldehydes, carboxylic acids, or denitrated compounds (Ono, 2001; Berner et al., 2002; Ballini & Petrini, 2004). As a contribution in this field, we have synthesized a series of nitroalkenes by employing benzaldehydes and nitroethane. We report here the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules. Both molecules adopt an E configuration with respect to the C═C double bond. In the crystal packing (Fig. 2), the molecules interact through π···π interactions (centroid-to-centroid distances of 3.695 (3) and 3.804 (3) Å) to form columns along the c axis. The column are further connected into a three-dimensional network by C—H···O hydrogen bonds (Table 1).

Related literature top

For background to the chemistry of nitroalkenes, see: Ballini & Petrini (2004); Berner et al. (2002); Ono (2001).

Experimental top

To a solution of 3-nitro-benzaldehyde (50 mmol) in AcOH (25 mL), nitroethane (75 mmol) was added, followed by butylamine (100 mmol, 7.4 mL). The mixture was sonicated at 60 °C, until GC showed full conversion of the aldehyde. The mixture was poured into ice water, the precipitate was filtered off, washed with water and recrystallized from EtOH/EtOAc to give the product. Single crystals were obtained by slow evaporation of an cyclohexane-EtOAc (10:1 v/v) solution.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The asymmetric unit of the title compound with the atomic labeling scheme; displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound showing the intermolecular hydrogen interaction dash lines. Displacement ellipsoids are drawn at the 50% probability level.

1-Nitro-4-(2-nitroprop-1-enyl)benzene top

Crystal data top

C₉H₈N₂O₄	F(000) = 864
M_r = 208.17	D_x = 1.424 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9423 reflections
a = 13.3621 (11) Å	θ = 3.0–27.5°
b = 9.7648 (7) Å	µ = 0.11 mm⁻¹
c = 14.8835 (11) Å	T = 296 K
β = 91.290 (2)°	Chunk, yellow
V = 1941.5 (3) Å³	0.38 × 0.29 × 0.20 mm
Z = 8

Data collection top

Rigaku R-AXIS RAPID diffractometer	4430 independent reflections
Radiation source: rolling anode	1883 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −17→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→11
T_min = 0.947, T_max = 0.978	l = −19→19
18620 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0633P)² + 0.4203P] where P = (F_o² + 2F_c²)/3
4430 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₉H₈N₂O₄	V = 1941.5 (3) Å³
M_r = 208.17	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3621 (11) Å	µ = 0.11 mm⁻¹
b = 9.7648 (7) Å	T = 296 K
c = 14.8835 (11) Å	0.38 × 0.29 × 0.20 mm
β = 91.290 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4430 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1883 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.978	R_int = 0.042
18620 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.01	Δρ_max = 0.24 e Å⁻³
4430 reflections	Δρ_min = −0.17 e Å⁻³
273 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
N1A	0.91640 (18)	0.3305 (3)	0.05652 (17)	0.0806 (6)
O2A	0.98875 (16)	0.3688 (2)	0.10125 (17)	0.1116 (8)
O1A	0.90989 (18)	0.2158 (2)	0.02430 (17)	0.1120 (8)
C4A	0.77860 (18)	0.6710 (2)	0.05586 (16)	0.0625 (6)
O1B	0.96098 (19)	0.2340 (2)	0.31850 (17)	0.1199 (8)
N1B	0.8836 (2)	0.2846 (3)	0.29171 (18)	0.0892 (7)
C3A	0.84789 (17)	0.5546 (3)	0.06249 (16)	0.0678 (7)
H3	0.9118	0.5744	0.0849	0.081*
C8B	0.59839 (19)	0.7663 (3)	0.31450 (16)	0.0679 (7)
C2A	0.83112 (17)	0.4254 (3)	0.04069 (16)	0.0658 (6)
C2B	0.86722 (19)	0.4327 (2)	0.30718 (17)	0.0673 (6)
C3B	0.77664 (18)	0.4791 (2)	0.28873 (17)	0.0692 (7)
H12	0.7304	0.4142	0.2686	0.083*
C9A	0.67661 (18)	0.6603 (2)	0.06964 (16)	0.0650 (6)
H9	0.6480	0.5753	0.0809	0.078*
O2B	0.8201 (2)	0.2192 (2)	0.2511 (2)	0.1380 (11)
C4B	0.73898 (18)	0.6202 (2)	0.29576 (16)	0.0617 (6)
C5B	0.7965 (2)	0.7370 (3)	0.28421 (18)	0.0723 (7)
H14	0.8646	0.7281	0.2739	0.087*
C9B	0.63788 (18)	0.6371 (2)	0.31073 (16)	0.0654 (6)
H18	0.5970	0.5611	0.3182	0.078*
C5A	0.8177 (2)	0.8007 (3)	0.04022 (18)	0.0761 (7)
H5	0.8861	0.8103	0.0316	0.091*
C6B	0.7547 (2)	0.8658 (3)	0.28776 (19)	0.0815 (8)
H15	0.7948	0.9426	0.2798	0.098*
N2B	0.4902 (2)	0.7794 (3)	0.32987 (19)	0.0929 (8)
N2A	0.51053 (19)	0.7625 (3)	0.08429 (18)	0.0910 (7)
C8A	0.6181 (2)	0.7759 (3)	0.06654 (17)	0.0702 (7)
O3A	0.47832 (17)	0.6518 (3)	0.0982 (3)	0.1743 (15)
O4A	0.45844 (19)	0.8608 (3)	0.0844 (2)	0.1402 (10)
O3B	0.4434 (2)	0.6811 (3)	0.3488 (3)	0.1726 (14)
C7B	0.6543 (2)	0.8819 (3)	0.30301 (18)	0.0791 (8)
H16	0.6254	0.9685	0.3054	0.095*
C1B	0.9567 (2)	0.5036 (3)	0.3453 (2)	0.0955 (9)
H10A	1.0044	0.5176	0.2989	0.143*
H10B	0.9864	0.4486	0.3923	0.143*
H10C	0.9373	0.5906	0.3694	0.143*
C7A	0.6564 (2)	0.9036 (3)	0.05062 (18)	0.0830 (8)
H7	0.6152	0.9804	0.0489	0.100*
C6A	0.7576 (2)	0.9148 (3)	0.0372 (2)	0.0894 (9)
H6	0.7855	1.0002	0.0261	0.107*
C1A	0.7418 (2)	0.3607 (3)	−0.0012 (2)	0.0956 (10)
H1A	0.6986	0.4302	−0.0261	0.143*
H1B	0.7067	0.3097	0.0433	0.143*
H1C	0.7621	0.3000	−0.0482	0.143*
O4B	0.45068 (18)	0.8883 (3)	0.3199 (2)	0.1367 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0647 (15)	0.0786 (16)	0.0986 (17)	0.0075 (12)	0.0091 (13)	0.0115 (14)
O2A	0.0697 (14)	0.1051 (16)	0.159 (2)	0.0148 (12)	−0.0217 (14)	0.0049 (14)
O1A	0.1112 (18)	0.0803 (14)	0.144 (2)	0.0245 (12)	0.0023 (15)	−0.0107 (14)
C4A	0.0590 (15)	0.0640 (14)	0.0643 (15)	−0.0041 (12)	−0.0004 (11)	−0.0001 (12)
O1B	0.1121 (19)	0.1086 (17)	0.139 (2)	0.0557 (14)	−0.0007 (15)	−0.0028 (14)
N1B	0.0780 (18)	0.0757 (16)	0.115 (2)	0.0129 (14)	0.0161 (15)	−0.0010 (14)
C3A	0.0511 (14)	0.0744 (17)	0.0777 (16)	−0.0019 (12)	0.0001 (12)	0.0052 (13)
C8B	0.0631 (16)	0.0704 (16)	0.0707 (16)	0.0113 (13)	0.0084 (12)	0.0049 (13)
C2A	0.0531 (14)	0.0678 (15)	0.0768 (16)	0.0032 (12)	0.0079 (12)	0.0024 (13)
C2B	0.0622 (16)	0.0583 (14)	0.0819 (17)	0.0033 (12)	0.0101 (13)	0.0052 (12)
C3B	0.0590 (16)	0.0599 (14)	0.0889 (18)	−0.0035 (12)	0.0080 (13)	0.0000 (13)
C9A	0.0589 (16)	0.0623 (14)	0.0737 (16)	−0.0003 (12)	−0.0039 (12)	0.0008 (12)
O2B	0.1084 (19)	0.0716 (14)	0.233 (3)	0.0038 (13)	−0.014 (2)	−0.0303 (16)
C4B	0.0582 (15)	0.0591 (14)	0.0679 (15)	0.0006 (11)	0.0022 (11)	0.0044 (11)
C5B	0.0627 (16)	0.0686 (17)	0.0855 (18)	−0.0032 (13)	0.0017 (13)	0.0030 (13)
C9B	0.0623 (16)	0.0596 (14)	0.0746 (16)	0.0002 (12)	0.0100 (12)	0.0079 (12)
C5A	0.0719 (17)	0.0695 (17)	0.0874 (18)	−0.0088 (14)	0.0090 (14)	0.0009 (14)
C6B	0.085 (2)	0.0610 (16)	0.099 (2)	−0.0130 (14)	0.0015 (16)	0.0029 (14)
N2B	0.0783 (18)	0.0790 (17)	0.122 (2)	0.0212 (15)	0.0218 (15)	0.0153 (15)
N2A	0.0680 (17)	0.0898 (18)	0.115 (2)	0.0143 (15)	−0.0088 (14)	0.0025 (15)
C8A	0.0630 (17)	0.0761 (17)	0.0713 (16)	0.0042 (13)	−0.0036 (13)	−0.0032 (13)
O3A	0.0603 (15)	0.124 (2)	0.339 (5)	0.0037 (15)	0.001 (2)	0.063 (3)
O4A	0.0951 (17)	0.1155 (19)	0.211 (3)	0.0362 (15)	0.0182 (17)	−0.0182 (18)
O3B	0.0914 (19)	0.124 (2)	0.306 (4)	0.0254 (16)	0.081 (2)	0.067 (2)
C7B	0.091 (2)	0.0597 (15)	0.0869 (19)	0.0108 (15)	0.0042 (16)	0.0013 (13)
C1B	0.0658 (18)	0.090 (2)	0.130 (3)	−0.0040 (15)	−0.0178 (17)	0.0151 (18)
C7A	0.095 (2)	0.0683 (18)	0.0855 (19)	0.0133 (16)	0.0029 (16)	0.0008 (14)
C6A	0.104 (2)	0.0625 (17)	0.103 (2)	−0.0088 (16)	0.0148 (18)	0.0029 (15)
C1A	0.0722 (19)	0.085 (2)	0.130 (3)	0.0024 (15)	−0.0080 (17)	−0.0250 (18)
O4B	0.0992 (18)	0.0986 (17)	0.213 (3)	0.0340 (14)	0.0132 (17)	0.0055 (17)

Geometric parameters (Å, º) top

N1A—O2A	1.220 (3)	C5B—C6B	1.378 (4)
N1A—O1A	1.220 (3)	C5B—H14	0.9300
N1A—C2A	1.484 (3)	C9B—H18	0.9300
C4A—C9A	1.387 (3)	C5A—C6A	1.374 (4)
C4A—C5A	1.392 (3)	C5A—H5	0.9300
C4A—C3A	1.468 (3)	C6B—C7B	1.375 (4)
O1B—N1B	1.206 (3)	C6B—H15	0.9300
N1B—O2B	1.212 (3)	N2B—O3B	1.183 (3)
N1B—C2B	1.482 (3)	N2B—O4B	1.195 (3)
C3A—C2A	1.320 (3)	N2A—O3A	1.184 (3)
C3A—H3	0.9300	N2A—O4A	1.186 (3)
C8B—C7B	1.366 (4)	N2A—C8A	1.474 (4)
C8B—C9B	1.369 (3)	C8A—C7A	1.370 (4)
C8B—N2B	1.474 (4)	C7B—H16	0.9300
C2A—C1A	1.476 (3)	C1B—H10A	0.9600
C2B—C3B	1.315 (3)	C1B—H10B	0.9600
C2B—C1B	1.484 (3)	C1B—H10C	0.9600
C3B—C4B	1.471 (3)	C7A—C6A	1.376 (4)
C3B—H12	0.9300	C7A—H7	0.9300
C9A—C8A	1.373 (3)	C6A—H6	0.9300
C9A—H9	0.9300	C1A—H1A	0.9600
C4B—C9B	1.384 (3)	C1A—H1B	0.9600
C4B—C5B	1.388 (3)	C1A—H1C	0.9600

O2A—N1A—O1A	123.0 (2)	C6A—C5A—C4A	121.4 (3)
O2A—N1A—C2A	119.4 (2)	C6A—C5A—H5	119.3
O1A—N1A—C2A	117.6 (2)	C4A—C5A—H5	119.3
C9A—C4A—C5A	117.9 (2)	C7B—C6B—C5B	120.6 (3)
C9A—C4A—C3A	123.5 (2)	C7B—C6B—H15	119.7
C5A—C4A—C3A	118.5 (2)	C5B—C6B—H15	119.7
O1B—N1B—O2B	122.2 (3)	O3B—N2B—O4B	121.1 (3)
O1B—N1B—C2B	118.5 (3)	O3B—N2B—C8B	119.4 (3)
O2B—N1B—C2B	119.2 (3)	O4B—N2B—C8B	119.4 (3)
C2A—C3A—C4A	128.3 (2)	O3A—N2A—O4A	121.6 (3)
C2A—C3A—H3	115.8	O3A—N2A—C8A	118.2 (3)
C4A—C3A—H3	115.8	O4A—N2A—C8A	120.2 (3)
C7B—C8B—C9B	123.0 (2)	C7A—C8A—C9A	122.7 (3)
C7B—C8B—N2B	119.2 (2)	C7A—C8A—N2A	118.7 (3)
C9B—C8B—N2B	117.8 (2)	C9A—C8A—N2A	118.5 (3)
C3A—C2A—C1A	130.1 (2)	C8B—C7B—C6B	117.7 (2)
C3A—C2A—N1A	115.6 (2)	C8B—C7B—H16	121.2
C1A—C2A—N1A	114.2 (2)	C6B—C7B—H16	121.2
C3B—C2B—N1B	116.2 (2)	C2B—C1B—H10A	109.5
C3B—C2B—C1B	130.5 (2)	C2B—C1B—H10B	109.5
N1B—C2B—C1B	113.2 (2)	H10A—C1B—H10B	109.5
C2B—C3B—C4B	128.5 (2)	C2B—C1B—H10C	109.5
C2B—C3B—H12	115.8	H10A—C1B—H10C	109.5
C4B—C3B—H12	115.8	H10B—C1B—H10C	109.5
C8A—C9A—C4A	119.5 (2)	C8A—C7A—C6A	118.0 (3)
C8A—C9A—H9	120.2	C8A—C7A—H7	121.0
C4A—C9A—H9	120.2	C6A—C7A—H7	121.0
C9B—C4B—C5B	117.8 (2)	C7A—C6A—C5A	120.5 (3)
C9B—C4B—C3B	117.4 (2)	C7A—C6A—H6	119.8
C5B—C4B—C3B	124.7 (2)	C5A—C6A—H6	119.8
C6B—C5B—C4B	121.3 (3)	C2A—C1A—H1A	109.5
C6B—C5B—H14	119.4	C2A—C1A—H1B	109.5
C4B—C5B—H14	119.4	H1A—C1A—H1B	109.5
C8B—C9B—C4B	119.7 (2)	C2A—C1A—H1C	109.5
C8B—C9B—H18	120.2	H1A—C1A—H1C	109.5
C4B—C9B—H18	120.2	H1B—C1A—H1C	109.5

C9A—C4A—C3A—C2A	34.4 (4)	C5B—C4B—C9B—C8B	−0.6 (4)
C5A—C4A—C3A—C2A	−149.6 (3)	C3B—C4B—C9B—C8B	−177.6 (2)
C4A—C3A—C2A—C1A	4.1 (5)	C9A—C4A—C5A—C6A	−0.8 (4)
C4A—C3A—C2A—N1A	−179.1 (2)	C3A—C4A—C5A—C6A	−177.1 (2)
O2A—N1A—C2A—C3A	12.3 (4)	C4B—C5B—C6B—C7B	0.0 (4)
O1A—N1A—C2A—C3A	−168.5 (3)	C7B—C8B—N2B—O3B	−172.5 (3)
O2A—N1A—C2A—C1A	−170.5 (3)	C9B—C8B—N2B—O3B	8.8 (4)
O1A—N1A—C2A—C1A	8.8 (4)	C7B—C8B—N2B—O4B	10.2 (4)
O1B—N1B—C2B—C3B	−170.4 (3)	C9B—C8B—N2B—O4B	−168.6 (3)
O2B—N1B—C2B—C3B	11.1 (4)	C4A—C9A—C8A—C7A	−0.3 (4)
O1B—N1B—C2B—C1B	7.1 (4)	C4A—C9A—C8A—N2A	−178.0 (2)
O2B—N1B—C2B—C1B	−171.3 (3)	O3A—N2A—C8A—C7A	−179.8 (3)
N1B—C2B—C3B—C4B	−178.8 (2)	O4A—N2A—C8A—C7A	0.3 (4)
C1B—C2B—C3B—C4B	4.2 (5)	O3A—N2A—C8A—C9A	−2.0 (4)
C5A—C4A—C9A—C8A	0.7 (3)	O4A—N2A—C8A—C9A	178.1 (3)
C3A—C4A—C9A—C8A	176.7 (2)	C9B—C8B—C7B—C6B	−0.5 (4)
C2B—C3B—C4B—C9B	−152.8 (3)	N2B—C8B—C7B—C6B	−179.3 (2)
C2B—C3B—C4B—C5B	30.4 (4)	C5B—C6B—C7B—C8B	0.1 (4)
C9B—C4B—C5B—C6B	0.2 (4)	C9A—C8A—C7A—C6A	0.1 (4)
C3B—C4B—C5B—C6B	177.0 (2)	N2A—C8A—C7A—C6A	177.8 (2)
C7B—C8B—C9B—C4B	0.8 (4)	C8A—C7A—C6A—C5A	−0.2 (4)
N2B—C8B—C9B—C4B	179.5 (2)	C4A—C5A—C6A—C7A	0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9B—H18···O4Aⁱ	0.93	2.55	3.386 (4)	149

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₉H₈N₂O₄
M_r	208.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.3621 (11), 9.7648 (7), 14.8835 (11)
β (°)	91.290 (2)
V (Å³)	1941.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.38 × 0.29 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.947, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	18620, 4430, 1883
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.168, 1.01
No. of reflections	4430
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.17

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9B—H18···O4Aⁱ	0.93	2.55	3.386 (4)	149

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

The authors thank Mr Jianming Gu for the X-ray single crystal analysis. We are also grateful for financial support from the Natural Science Foundation of Zhejiang Province Education Department (No. Y200803565).

References

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