N-(2,4-Dinitro­phen­yl)-1,3-dimeth­oxy­isoindolin-2-amine

Du, N.-N.; Xu, H.-J.; Sheng, L.-Q.

doi:10.1107/S1600536811026316

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1970

doi:10.1107/S1600536811026316

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N-(2,4-Dinitrophenyl)-1,3-dimethoxyisoindolin-2-amine

Na-Na Du,^a Hua-Jie Xu ^a and Liang-Quan Sheng ^a ^*

^aDepartment of Chemistry, Fuyang Normal College, Fuyang, Anhui 236041, People's Republic of China
^*Correspondence e-mail: shenglq@fync.edu.cn

(Received 15 May 2011; accepted 2 July 2011; online 9 July 2011)

In the title compound, C₁₆H₁₆N₄O₆, the planes of the isoindole and dinitrobenzene groups make a dihedral angle between of 84.15 (8)°. The N atom of the isoindole group is displaced by 0.2937 (3) Å from the plane through the remaining atoms. An intramolecular N—H⋯O interaction occurs. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur.

Related literature

For general background to isoindoles and their derivatives, see: Mancilla et al. (2007 ); Toru et al. (1986 ). For the synthetic method and related structures, see: Maliha et al. (2008 , 2009 ).

Experimental

Crystal data

C₁₆H₁₆N₄O₆
M_r = 360.33
Triclinic, $[P \overline 1]$
a = 7.727 (4) Å
b = 10.244 (5) Å
c = 11.326 (6) Å
α = 86.076 (9)°
β = 77.705 (8)°
γ = 70.794 (8)°
V = 827.2 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.16 × 0.14 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.982, T_max = 0.989
4365 measured reflections
3181 independent reflections
2045 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.225
S = 1.02
3181 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.96	2.593 (3)	130
N2—H2A⋯O1ⁱ	0.86	2.27	3.032 (3)	148
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); 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/S1600536811026316/ez2248sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026316/ez2248Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026316/ez2248Isup3.cml

checkCIF report

Comment top

Isoindoles and their derivatives are of great pharmaceutical importance (Mancilla et al., 2007). In addition, some derivatives of isoindoles have shown a wide range of herbicidal activities (Toru et al., 1986). Here, the synthesis and characterization with X-ray crystallography of a new derivative is described.

The molecule of the title compound (Fig. 1), is similar to the previously reported compound, 1,3-dimethoxy-2,3-dihydro-1H-isoindole-2-carbothioamide, with its bond lengths and angles being within normal ranges (Maliha et al., 2009). Ring A (C1—C6) is planar, while the five-membered ring B (N1/C5/C6/C7/C8) adopts an envelope conformation with atom N1 displaced by 0.320 (3) Å from the plane of the other ring atoms. The molecule contains a pseudo mirror plane, with the symmetrical orientations of the O-CH₃ groups leading to R and S-configurations at carbon atoms C7 and C8, respectively. The crystal structure is stabilized by an intramolecular N—H···O interaction and an intermolecular N—H···O interaction (see Table 1), which links a pair of molecules to form a dimer (Fig. 2).

Related literature top

For general background to isoindoles and their derivatives, see: Mancilla et al. (2007); Toru et al. (1986). For the synthetic method and related structures, see: Maliha et al. (2008, 2009).

Experimental top

All reagents and solvents were used as obtained commercially without further purification. The title compound was prepared according to the reported procedure (Maliha et al., 2009). For the preparation of the title compound, a mixture of ortho-phthaldehyde (1.34 g, 10 mmol) and 2, 4-dinitrophenylhydrazine (1.98 g, 10 mmol) in 20 ml of methanol, and aqueous NaOH (5 ml, 5%) was added dropwise with constant stirring. Then, it was further refluxed in methanol for 2 h, and left to stand overnight. After 3 h, a colorless precipitate was obtained, which was washed with hexane, ethanol and acetone, respectively. Crystals suitable for X-ray analysis were obtained from a solution of acetone/methanol mixture by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The dimeric structure of the title compound formed by intermolecular hydrogen bonds. The intra- and intermolecular hydrogen bonds are shown as green dashed lines.

N-(2,4-Dinitrophenyl)-1,3-dimethoxyisoindolin-2-amine top

Crystal data top

C₁₆H₁₆N₄O₆	Z = 2
M_r = 360.33	F(000) = 376
Triclinic, P1	D_x = 1.447 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.727 (4) Å	Cell parameters from 1638 reflections
b = 10.244 (5) Å	θ = 2.8–27.5°
c = 11.326 (6) Å	µ = 0.11 mm⁻¹
α = 86.076 (9)°	T = 296 K
β = 77.705 (8)°	Block, colorless
γ = 70.794 (8)°	0.16 × 0.14 × 0.10 mm
V = 827.2 (7) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3181 independent reflections
Radiation source: fine-focus sealed tube	2045 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
phi and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.982, T_max = 0.989	k = −11→12
4365 measured reflections	l = −13→13

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.225	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1489P)²] where P = (F_o² + 2F_c²)/3
3181 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₁₆N₄O₆	γ = 70.794 (8)°
M_r = 360.33	V = 827.2 (7) Å³
Triclinic, P1	Z = 2
a = 7.727 (4) Å	Mo Kα radiation
b = 10.244 (5) Å	µ = 0.11 mm⁻¹
c = 11.326 (6) Å	T = 296 K
α = 86.076 (9)°	0.16 × 0.14 × 0.10 mm
β = 77.705 (8)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3181 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2045 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.989	R_int = 0.062
4365 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.225	H-atom parameters constrained
S = 1.02	Δρ_max = 0.49 e Å⁻³
3181 reflections	Δρ_min = −0.25 e Å⁻³
237 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
C1	0.1312 (5)	0.1163 (3)	0.6041 (3)	0.0665 (9)
H1	0.1032	0.0400	0.6417	0.080*
C2	0.1069 (5)	0.1515 (4)	0.4885 (3)	0.0741 (10)
H2	0.0623	0.0983	0.4471	0.089*
C3	0.1476 (5)	0.2646 (4)	0.4328 (3)	0.0684 (9)
H3	0.1297	0.2869	0.3543	0.082*
C4	0.2142 (4)	0.3446 (3)	0.4915 (3)	0.0588 (8)
H4	0.2414	0.4212	0.4539	0.071*
C5	0.2401 (4)	0.3088 (3)	0.6080 (2)	0.0451 (6)
C6	0.1985 (4)	0.1974 (3)	0.6640 (2)	0.0487 (7)
C7	0.2308 (4)	0.1839 (3)	0.7897 (2)	0.0501 (7)
H7	0.1096	0.2205	0.8450	0.060*
C8	0.3055 (4)	0.3813 (3)	0.6914 (2)	0.0450 (6)
H8	0.2013	0.4633	0.7241	0.054*
C9	0.4404 (3)	0.3127 (2)	0.9664 (2)	0.0404 (6)
C10	0.4134 (3)	0.3760 (2)	1.0796 (2)	0.0405 (6)
C11	0.5561 (4)	0.3448 (2)	1.1440 (2)	0.0436 (6)
H11	0.5367	0.3873	1.2179	0.052*
C12	0.7242 (4)	0.2512 (3)	1.0975 (2)	0.0478 (7)
C13	0.7560 (4)	0.1846 (3)	0.9883 (2)	0.0516 (7)
H13	0.8714	0.1193	0.9589	0.062*
C14	0.6169 (4)	0.2160 (3)	0.9250 (2)	0.0496 (7)
H14	0.6395	0.1717	0.8516	0.060*
C15	0.4939 (5)	−0.0207 (3)	0.7495 (4)	0.0802 (10)
H15A	0.4677	−0.0681	0.6887	0.120*
H15B	0.5744	−0.0866	0.7950	0.120*
H15C	0.5546	0.0439	0.7116	0.120*
C16	0.6218 (5)	0.3179 (3)	0.5833 (3)	0.0656 (8)
H16A	0.6744	0.2530	0.6417	0.098*
H16B	0.7128	0.3590	0.5413	0.098*
H16C	0.5869	0.2708	0.5265	0.098*
N1	0.3375 (3)	0.2795 (2)	0.78934 (18)	0.0438 (5)
N2	0.3060 (3)	0.3424 (2)	0.90125 (19)	0.0499 (6)
H2A	0.1982	0.4013	0.9289	0.060*
N3	0.2382 (3)	0.4743 (2)	1.13435 (19)	0.0478 (6)
N4	0.8726 (4)	0.2154 (3)	1.1652 (3)	0.0671 (8)
O1	0.1085 (3)	0.5064 (3)	1.0803 (2)	0.0811 (8)
O2	0.2215 (3)	0.5263 (2)	1.23014 (19)	0.0758 (7)
O3	1.0248 (4)	0.1387 (4)	1.1204 (3)	0.1139 (12)
O4	0.8371 (4)	0.2619 (3)	1.2668 (3)	0.1046 (11)
O5	0.3227 (3)	0.0518 (2)	0.8286 (2)	0.0697 (6)
O6	0.4614 (3)	0.42259 (18)	0.64289 (17)	0.0553 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.078 (2)	0.0666 (19)	0.071 (2)	−0.0393 (17)	−0.0207 (17)	−0.0068 (15)
C2	0.078 (2)	0.087 (2)	0.073 (2)	−0.0333 (19)	−0.0310 (18)	−0.0206 (18)
C3	0.077 (2)	0.082 (2)	0.0539 (18)	−0.0243 (18)	−0.0284 (16)	−0.0103 (16)
C4	0.074 (2)	0.0550 (17)	0.0505 (17)	−0.0184 (15)	−0.0220 (14)	−0.0007 (13)
C5	0.0475 (15)	0.0434 (13)	0.0443 (14)	−0.0093 (11)	−0.0157 (11)	−0.0063 (11)
C6	0.0502 (15)	0.0503 (15)	0.0488 (15)	−0.0158 (12)	−0.0156 (12)	−0.0062 (12)
C7	0.0563 (16)	0.0491 (15)	0.0472 (15)	−0.0189 (12)	−0.0116 (12)	−0.0027 (12)
C8	0.0533 (15)	0.0390 (13)	0.0429 (14)	−0.0110 (11)	−0.0147 (11)	−0.0043 (10)
C9	0.0470 (14)	0.0391 (13)	0.0373 (13)	−0.0139 (11)	−0.0139 (11)	0.0029 (10)
C10	0.0463 (14)	0.0361 (12)	0.0380 (13)	−0.0112 (10)	−0.0100 (11)	0.0007 (10)
C11	0.0552 (16)	0.0383 (13)	0.0406 (14)	−0.0156 (11)	−0.0160 (12)	0.0006 (10)
C12	0.0504 (16)	0.0435 (14)	0.0530 (16)	−0.0139 (12)	−0.0208 (12)	0.0029 (11)
C13	0.0493 (16)	0.0480 (15)	0.0534 (16)	−0.0084 (12)	−0.0127 (13)	−0.0026 (12)
C14	0.0523 (16)	0.0522 (15)	0.0425 (14)	−0.0110 (13)	−0.0131 (12)	−0.0060 (12)
C15	0.087 (3)	0.0460 (17)	0.101 (3)	−0.0132 (17)	−0.020 (2)	0.0006 (17)
C16	0.067 (2)	0.0663 (19)	0.0624 (19)	−0.0253 (16)	−0.0027 (15)	−0.0038 (15)
N1	0.0538 (13)	0.0420 (11)	0.0369 (11)	−0.0127 (10)	−0.0142 (9)	−0.0062 (9)
N2	0.0485 (13)	0.0547 (13)	0.0413 (12)	−0.0047 (10)	−0.0136 (10)	−0.0118 (10)
N3	0.0526 (13)	0.0487 (12)	0.0406 (12)	−0.0100 (10)	−0.0152 (10)	−0.0038 (9)
N4	0.0626 (17)	0.0641 (16)	0.0746 (18)	−0.0036 (13)	−0.0367 (14)	−0.0125 (14)
O1	0.0548 (13)	0.1044 (18)	0.0684 (15)	0.0123 (12)	−0.0283 (11)	−0.0361 (13)
O2	0.0744 (15)	0.0890 (16)	0.0526 (13)	0.0012 (12)	−0.0230 (11)	−0.0312 (11)
O3	0.0634 (16)	0.139 (3)	0.122 (2)	0.0166 (17)	−0.0444 (16)	−0.052 (2)
O4	0.0970 (19)	0.111 (2)	0.094 (2)	0.0161 (16)	−0.0634 (16)	−0.0374 (17)
O5	0.0905 (16)	0.0517 (12)	0.0685 (14)	−0.0258 (11)	−0.0194 (12)	0.0151 (10)
O6	0.0670 (13)	0.0474 (11)	0.0574 (12)	−0.0267 (10)	−0.0108 (10)	−0.0039 (9)

Geometric parameters (Å, º) top

C1—C2	1.369 (5)	C10—N3	1.436 (3)
C1—C6	1.390 (4)	C11—C12	1.357 (4)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.376 (5)	C12—C13	1.390 (4)
C2—H2	0.9300	C12—N4	1.448 (4)
C3—C4	1.370 (4)	C13—C14	1.358 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.384 (4)	C14—H14	0.9300
C4—H4	0.9300	C15—O5	1.430 (4)
C5—C6	1.365 (4)	C15—H15A	0.9600
C5—C8	1.499 (3)	C15—H15B	0.9600
C6—C7	1.486 (4)	C15—H15C	0.9600
C7—O5	1.396 (4)	C16—O6	1.418 (4)
C7—N1	1.473 (3)	C16—H16A	0.9600
C7—H7	0.9800	C16—H16B	0.9600
C8—O6	1.397 (3)	C16—H16C	0.9600
C8—N1	1.472 (3)	N1—N2	1.399 (3)
C8—H8	0.9800	N2—H2A	0.8600
C9—N2	1.343 (3)	N3—O2	1.205 (3)
C9—C14	1.401 (4)	N3—O1	1.227 (3)
C9—C10	1.421 (3)	N4—O3	1.204 (3)
C10—C11	1.388 (4)	N4—O4	1.217 (3)

C2—C1—C6	118.4 (3)	C12—C11—H11	120.5
C2—C1—H1	120.8	C10—C11—H11	120.5
C6—C1—H1	120.8	C11—C12—C13	121.7 (2)
C1—C2—C3	121.0 (3)	C11—C12—N4	119.4 (3)
C1—C2—H2	119.5	C13—C12—N4	118.8 (2)
C3—C2—H2	119.5	C14—C13—C12	119.3 (3)
C4—C3—C2	120.8 (3)	C14—C13—H13	120.4
C4—C3—H3	119.6	C12—C13—H13	120.4
C2—C3—H3	119.6	C13—C14—C9	122.3 (2)
C3—C4—C5	118.4 (3)	C13—C14—H14	118.8
C3—C4—H4	120.8	C9—C14—H14	118.8
C5—C4—H4	120.8	O5—C15—H15A	109.5
C6—C5—C4	121.1 (3)	O5—C15—H15B	109.5
C6—C5—C8	110.5 (2)	H15A—C15—H15B	109.5
C4—C5—C8	128.4 (3)	O5—C15—H15C	109.5
C5—C6—C1	120.4 (3)	H15A—C15—H15C	109.5
C5—C6—C7	110.8 (2)	H15B—C15—H15C	109.5
C1—C6—C7	128.8 (3)	O6—C16—H16A	109.5
O5—C7—N1	112.1 (2)	O6—C16—H16B	109.5
O5—C7—C6	117.2 (2)	H16A—C16—H16B	109.5
N1—C7—C6	101.9 (2)	O6—C16—H16C	109.5
O5—C7—H7	108.4	H16A—C16—H16C	109.5
N1—C7—H7	108.4	H16B—C16—H16C	109.5
C6—C7—H7	108.4	N2—N1—C8	112.18 (19)
O6—C8—N1	113.0 (2)	N2—N1—C7	113.7 (2)
O6—C8—C5	117.0 (2)	C8—N1—C7	110.43 (19)
N1—C8—C5	101.6 (2)	C9—N2—N1	121.4 (2)
O6—C8—H8	108.3	C9—N2—H2A	119.3
N1—C8—H8	108.3	N1—N2—H2A	119.3
C5—C8—H8	108.3	O2—N3—O1	121.1 (2)
N2—C9—C14	121.0 (2)	O2—N3—C10	120.2 (2)
N2—C9—C10	122.7 (2)	O1—N3—C10	118.7 (2)
C14—C9—C10	116.3 (2)	O3—N4—O4	122.5 (3)
C11—C10—C9	121.4 (2)	O3—N4—C12	119.1 (3)
C11—C10—N3	116.3 (2)	O4—N4—C12	118.4 (3)
C9—C10—N3	122.3 (2)	C7—O5—C15	114.8 (2)
C12—C11—C10	118.9 (2)	C8—O6—C16	115.8 (2)

C6—C1—C2—C3	−0.2 (5)	N4—C12—C13—C14	179.1 (3)
C1—C2—C3—C4	0.2 (5)	C12—C13—C14—C9	−0.6 (4)
C2—C3—C4—C5	0.2 (5)	N2—C9—C14—C13	179.4 (2)
C3—C4—C5—C6	−0.7 (4)	C10—C9—C14—C13	−0.6 (4)
C3—C4—C5—C8	−178.1 (3)	O6—C8—N1—N2	84.6 (3)
C4—C5—C6—C1	0.8 (4)	C5—C8—N1—N2	−149.3 (2)
C8—C5—C6—C1	178.6 (3)	O6—C8—N1—C7	−147.5 (2)
C4—C5—C6—C7	−177.7 (2)	C5—C8—N1—C7	−21.3 (3)
C8—C5—C6—C7	0.2 (3)	O5—C7—N1—N2	−85.2 (3)
C2—C1—C6—C5	−0.3 (5)	C6—C7—N1—N2	148.6 (2)
C2—C1—C6—C7	177.8 (3)	O5—C7—N1—C8	147.7 (2)
C5—C6—C7—O5	−135.8 (3)	C6—C7—N1—C8	21.5 (3)
C1—C6—C7—O5	46.0 (4)	C14—C9—N2—N1	−0.8 (4)
C5—C6—C7—N1	−13.0 (3)	C10—C9—N2—N1	179.2 (2)
C1—C6—C7—N1	168.7 (3)	C8—N1—N2—C9	−122.1 (3)
C6—C5—C8—O6	136.2 (2)	C7—N1—N2—C9	111.7 (3)
C4—C5—C8—O6	−46.1 (4)	C11—C10—N3—O2	1.0 (4)
C6—C5—C8—N1	12.7 (3)	C9—C10—N3—O2	−179.5 (3)
C4—C5—C8—N1	−169.6 (3)	C11—C10—N3—O1	179.2 (2)
N2—C9—C10—C11	−179.0 (2)	C9—C10—N3—O1	−1.4 (4)
C14—C9—C10—C11	1.0 (4)	C11—C12—N4—O3	−175.6 (3)
N2—C9—C10—N3	1.6 (4)	C13—C12—N4—O3	6.7 (5)
C14—C9—C10—N3	−178.4 (2)	C11—C12—N4—O4	6.0 (5)
C9—C10—C11—C12	−0.3 (4)	C13—C12—N4—O4	−171.6 (3)
N3—C10—C11—C12	179.2 (2)	N1—C7—O5—C15	−66.5 (3)
C10—C11—C12—C13	−1.0 (4)	C6—C7—O5—C15	50.8 (3)
C10—C11—C12—N4	−178.6 (2)	N1—C8—O6—C16	64.6 (3)
C11—C12—C13—C14	1.5 (4)	C5—C8—O6—C16	−52.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.96	2.593 (3)	130
N2—H2A···O1ⁱ	0.86	2.27	3.032 (3)	148

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₄O₆
M_r	360.33
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.727 (4), 10.244 (5), 11.326 (6)
α, β, γ (°)	86.076 (9), 77.705 (8), 70.794 (8)
V (Å³)	827.2 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.16 × 0.14 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	4365, 3181, 2045
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.225, 1.02
No. of reflections	3181
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.25

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), 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
N2—H2A···O1	0.86	1.96	2.593 (3)	130
N2—H2A···O1ⁱ	0.86	2.27	3.032 (3)	148

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

This work was supported by the Key Project of Science and Technology of Anhui, (grant No. 08010302218), the Natural Science Foundation of Anhui Provincial University (grant No. KJ2009A127) and the National Natural Science Foundation of China (grant No. 20971024).

References

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