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

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COMMUNICATIONS
ISSN: 2056-9890

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

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[Mancilla, T., Correa-Basurto, J. C., Carbajal, K. S. A., Escalante, E. T. J. S. & Ferrara, J. T. (2007). J. Mex. Chem. Soc. E51, 96-102.]); Toru et al. (1986[Toru, H., Eiki, N., Ryo, Y. & Shunichi, H. (1986). US Patent No. 4 595 409.]). For the synthetic method and related structures, see: Maliha et al. (2008[Maliha, B., Hussain, I., Tahir, M. N., Tariq, M. I. & Siddiqui, H. L. (2008). Acta Cryst. E64, o626.], 2009[Maliha, B., Tariq, M. I., Tahir, M. N., Hussain, I. & Ali, M. (2009). Acta Cryst. E65, o41.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N4O6

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.982, Tmax = 0.989

  • 4365 measured reflections

  • 3181 independent reflections

  • 2045 reflections with I > 2σ(I)

  • Rint = 0.062

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.225

  • S = 1.02

  • 3181 reflections

  • 237 parameters

  • H-atom parameters constrained

  • Δρmax = 0.49 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). APEX2 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

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.

Refinement top

H atoms bonded to C atoms were placed geometrically and treated as riding, with C—H distances 0.93–0.98Å and Uiso(H) = 1.2Ueq(C) for the CH while Uiso(H) = 1.5Ueq(C) for the CH3 groups. The amide H atoms were located from difference maps and refined with the N—H distances restrained to 0.86 Å and Uiso(H) = 1.2Ueq(N).

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
[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. 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
C16H16N4O6Z = 2
Mr = 360.33F(000) = 376
Triclinic, P1Dx = 1.447 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.727 (4) ÅCell parameters from 1638 reflections
b = 10.244 (5) Åθ = 2.8–27.5°
c = 11.326 (6) ŵ = 0.11 mm1
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 tube2045 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
phi and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 98
Tmin = 0.982, Tmax = 0.989k = 1112
4365 measured reflectionsl = 1313
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1489P)2]
where P = (Fo2 + 2Fc2)/3
3181 reflections(Δ/σ)max < 0.001
237 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C16H16N4O6γ = 70.794 (8)°
Mr = 360.33V = 827.2 (7) Å3
Triclinic, P1Z = 2
a = 7.727 (4) ÅMo Kα radiation
b = 10.244 (5) ŵ = 0.11 mm1
c = 11.326 (6) ÅT = 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)
Tmin = 0.982, Tmax = 0.989Rint = 0.062
4365 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.225H-atom parameters constrained
S = 1.02Δρmax = 0.49 e Å3
3181 reflectionsΔρmin = 0.25 e Å3
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
xyzUiso*/Ueq
C10.1312 (5)0.1163 (3)0.6041 (3)0.0665 (9)
H10.10320.04000.64170.080*
C20.1069 (5)0.1515 (4)0.4885 (3)0.0741 (10)
H20.06230.09830.44710.089*
C30.1476 (5)0.2646 (4)0.4328 (3)0.0684 (9)
H30.12970.28690.35430.082*
C40.2142 (4)0.3446 (3)0.4915 (3)0.0588 (8)
H40.24140.42120.45390.071*
C50.2401 (4)0.3088 (3)0.6080 (2)0.0451 (6)
C60.1985 (4)0.1974 (3)0.6640 (2)0.0487 (7)
C70.2308 (4)0.1839 (3)0.7897 (2)0.0501 (7)
H70.10960.22050.84500.060*
C80.3055 (4)0.3813 (3)0.6914 (2)0.0450 (6)
H80.20130.46330.72410.054*
C90.4404 (3)0.3127 (2)0.9664 (2)0.0404 (6)
C100.4134 (3)0.3760 (2)1.0796 (2)0.0405 (6)
C110.5561 (4)0.3448 (2)1.1440 (2)0.0436 (6)
H110.53670.38731.21790.052*
C120.7242 (4)0.2512 (3)1.0975 (2)0.0478 (7)
C130.7560 (4)0.1846 (3)0.9883 (2)0.0516 (7)
H130.87140.11930.95890.062*
C140.6169 (4)0.2160 (3)0.9250 (2)0.0496 (7)
H140.63950.17170.85160.060*
C150.4939 (5)0.0207 (3)0.7495 (4)0.0802 (10)
H15A0.46770.06810.68870.120*
H15B0.57440.08660.79500.120*
H15C0.55460.04390.71160.120*
C160.6218 (5)0.3179 (3)0.5833 (3)0.0656 (8)
H16A0.67440.25300.64170.098*
H16B0.71280.35900.54130.098*
H16C0.58690.27080.52650.098*
N10.3375 (3)0.2795 (2)0.78934 (18)0.0438 (5)
N20.3060 (3)0.3424 (2)0.90125 (19)0.0499 (6)
H2A0.19820.40130.92890.060*
N30.2382 (3)0.4743 (2)1.13435 (19)0.0478 (6)
N40.8726 (4)0.2154 (3)1.1652 (3)0.0671 (8)
O10.1085 (3)0.5064 (3)1.0803 (2)0.0811 (8)
O20.2215 (3)0.5263 (2)1.23014 (19)0.0758 (7)
O31.0248 (4)0.1387 (4)1.1204 (3)0.1139 (12)
O40.8371 (4)0.2619 (3)1.2668 (3)0.1046 (11)
O50.3227 (3)0.0518 (2)0.8286 (2)0.0697 (6)
O60.4614 (3)0.42259 (18)0.64289 (17)0.0553 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.078 (2)0.0666 (19)0.071 (2)0.0393 (17)0.0207 (17)0.0068 (15)
C20.078 (2)0.087 (2)0.073 (2)0.0333 (19)0.0310 (18)0.0206 (18)
C30.077 (2)0.082 (2)0.0539 (18)0.0243 (18)0.0284 (16)0.0103 (16)
C40.074 (2)0.0550 (17)0.0505 (17)0.0184 (15)0.0220 (14)0.0007 (13)
C50.0475 (15)0.0434 (13)0.0443 (14)0.0093 (11)0.0157 (11)0.0063 (11)
C60.0502 (15)0.0503 (15)0.0488 (15)0.0158 (12)0.0156 (12)0.0062 (12)
C70.0563 (16)0.0491 (15)0.0472 (15)0.0189 (12)0.0116 (12)0.0027 (12)
C80.0533 (15)0.0390 (13)0.0429 (14)0.0110 (11)0.0147 (11)0.0043 (10)
C90.0470 (14)0.0391 (13)0.0373 (13)0.0139 (11)0.0139 (11)0.0029 (10)
C100.0463 (14)0.0361 (12)0.0380 (13)0.0112 (10)0.0100 (11)0.0007 (10)
C110.0552 (16)0.0383 (13)0.0406 (14)0.0156 (11)0.0160 (12)0.0006 (10)
C120.0504 (16)0.0435 (14)0.0530 (16)0.0139 (12)0.0208 (12)0.0029 (11)
C130.0493 (16)0.0480 (15)0.0534 (16)0.0084 (12)0.0127 (13)0.0026 (12)
C140.0523 (16)0.0522 (15)0.0425 (14)0.0110 (13)0.0131 (12)0.0060 (12)
C150.087 (3)0.0460 (17)0.101 (3)0.0132 (17)0.020 (2)0.0006 (17)
C160.067 (2)0.0663 (19)0.0624 (19)0.0253 (16)0.0027 (15)0.0038 (15)
N10.0538 (13)0.0420 (11)0.0369 (11)0.0127 (10)0.0142 (9)0.0062 (9)
N20.0485 (13)0.0547 (13)0.0413 (12)0.0047 (10)0.0136 (10)0.0118 (10)
N30.0526 (13)0.0487 (12)0.0406 (12)0.0100 (10)0.0152 (10)0.0038 (9)
N40.0626 (17)0.0641 (16)0.0746 (18)0.0036 (13)0.0367 (14)0.0125 (14)
O10.0548 (13)0.1044 (18)0.0684 (15)0.0123 (12)0.0283 (11)0.0361 (13)
O20.0744 (15)0.0890 (16)0.0526 (13)0.0012 (12)0.0230 (11)0.0312 (11)
O30.0634 (16)0.139 (3)0.122 (2)0.0166 (17)0.0444 (16)0.052 (2)
O40.0970 (19)0.111 (2)0.094 (2)0.0161 (16)0.0634 (16)0.0374 (17)
O50.0905 (16)0.0517 (12)0.0685 (14)0.0258 (11)0.0194 (12)0.0151 (10)
O60.0670 (13)0.0474 (11)0.0574 (12)0.0267 (10)0.0108 (10)0.0039 (9)
Geometric parameters (Å, º) top
C1—C21.369 (5)C10—N31.436 (3)
C1—C61.390 (4)C11—C121.357 (4)
C1—H10.9300C11—H110.9300
C2—C31.376 (5)C12—C131.390 (4)
C2—H20.9300C12—N41.448 (4)
C3—C41.370 (4)C13—C141.358 (4)
C3—H30.9300C13—H130.9300
C4—C51.384 (4)C14—H140.9300
C4—H40.9300C15—O51.430 (4)
C5—C61.365 (4)C15—H15A0.9600
C5—C81.499 (3)C15—H15B0.9600
C6—C71.486 (4)C15—H15C0.9600
C7—O51.396 (4)C16—O61.418 (4)
C7—N11.473 (3)C16—H16A0.9600
C7—H70.9800C16—H16B0.9600
C8—O61.397 (3)C16—H16C0.9600
C8—N11.472 (3)N1—N21.399 (3)
C8—H80.9800N2—H2A0.8600
C9—N21.343 (3)N3—O21.205 (3)
C9—C141.401 (4)N3—O11.227 (3)
C9—C101.421 (3)N4—O31.204 (3)
C10—C111.388 (4)N4—O41.217 (3)
C2—C1—C6118.4 (3)C12—C11—H11120.5
C2—C1—H1120.8C10—C11—H11120.5
C6—C1—H1120.8C11—C12—C13121.7 (2)
C1—C2—C3121.0 (3)C11—C12—N4119.4 (3)
C1—C2—H2119.5C13—C12—N4118.8 (2)
C3—C2—H2119.5C14—C13—C12119.3 (3)
C4—C3—C2120.8 (3)C14—C13—H13120.4
C4—C3—H3119.6C12—C13—H13120.4
C2—C3—H3119.6C13—C14—C9122.3 (2)
C3—C4—C5118.4 (3)C13—C14—H14118.8
C3—C4—H4120.8C9—C14—H14118.8
C5—C4—H4120.8O5—C15—H15A109.5
C6—C5—C4121.1 (3)O5—C15—H15B109.5
C6—C5—C8110.5 (2)H15A—C15—H15B109.5
C4—C5—C8128.4 (3)O5—C15—H15C109.5
C5—C6—C1120.4 (3)H15A—C15—H15C109.5
C5—C6—C7110.8 (2)H15B—C15—H15C109.5
C1—C6—C7128.8 (3)O6—C16—H16A109.5
O5—C7—N1112.1 (2)O6—C16—H16B109.5
O5—C7—C6117.2 (2)H16A—C16—H16B109.5
N1—C7—C6101.9 (2)O6—C16—H16C109.5
O5—C7—H7108.4H16A—C16—H16C109.5
N1—C7—H7108.4H16B—C16—H16C109.5
C6—C7—H7108.4N2—N1—C8112.18 (19)
O6—C8—N1113.0 (2)N2—N1—C7113.7 (2)
O6—C8—C5117.0 (2)C8—N1—C7110.43 (19)
N1—C8—C5101.6 (2)C9—N2—N1121.4 (2)
O6—C8—H8108.3C9—N2—H2A119.3
N1—C8—H8108.3N1—N2—H2A119.3
C5—C8—H8108.3O2—N3—O1121.1 (2)
N2—C9—C14121.0 (2)O2—N3—C10120.2 (2)
N2—C9—C10122.7 (2)O1—N3—C10118.7 (2)
C14—C9—C10116.3 (2)O3—N4—O4122.5 (3)
C11—C10—C9121.4 (2)O3—N4—C12119.1 (3)
C11—C10—N3116.3 (2)O4—N4—C12118.4 (3)
C9—C10—N3122.3 (2)C7—O5—C15114.8 (2)
C12—C11—C10118.9 (2)C8—O6—C16115.8 (2)
C6—C1—C2—C30.2 (5)N4—C12—C13—C14179.1 (3)
C1—C2—C3—C40.2 (5)C12—C13—C14—C90.6 (4)
C2—C3—C4—C50.2 (5)N2—C9—C14—C13179.4 (2)
C3—C4—C5—C60.7 (4)C10—C9—C14—C130.6 (4)
C3—C4—C5—C8178.1 (3)O6—C8—N1—N284.6 (3)
C4—C5—C6—C10.8 (4)C5—C8—N1—N2149.3 (2)
C8—C5—C6—C1178.6 (3)O6—C8—N1—C7147.5 (2)
C4—C5—C6—C7177.7 (2)C5—C8—N1—C721.3 (3)
C8—C5—C6—C70.2 (3)O5—C7—N1—N285.2 (3)
C2—C1—C6—C50.3 (5)C6—C7—N1—N2148.6 (2)
C2—C1—C6—C7177.8 (3)O5—C7—N1—C8147.7 (2)
C5—C6—C7—O5135.8 (3)C6—C7—N1—C821.5 (3)
C1—C6—C7—O546.0 (4)C14—C9—N2—N10.8 (4)
C5—C6—C7—N113.0 (3)C10—C9—N2—N1179.2 (2)
C1—C6—C7—N1168.7 (3)C8—N1—N2—C9122.1 (3)
C6—C5—C8—O6136.2 (2)C7—N1—N2—C9111.7 (3)
C4—C5—C8—O646.1 (4)C11—C10—N3—O21.0 (4)
C6—C5—C8—N112.7 (3)C9—C10—N3—O2179.5 (3)
C4—C5—C8—N1169.6 (3)C11—C10—N3—O1179.2 (2)
N2—C9—C10—C11179.0 (2)C9—C10—N3—O11.4 (4)
C14—C9—C10—C111.0 (4)C11—C12—N4—O3175.6 (3)
N2—C9—C10—N31.6 (4)C13—C12—N4—O36.7 (5)
C14—C9—C10—N3178.4 (2)C11—C12—N4—O46.0 (5)
C9—C10—C11—C120.3 (4)C13—C12—N4—O4171.6 (3)
N3—C10—C11—C12179.2 (2)N1—C7—O5—C1566.5 (3)
C10—C11—C12—C131.0 (4)C6—C7—O5—C1550.8 (3)
C10—C11—C12—N4178.6 (2)N1—C8—O6—C1664.6 (3)
C11—C12—C13—C141.5 (4)C5—C8—O6—C1652.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.861.962.593 (3)130
N2—H2A···O1i0.862.273.032 (3)148
Symmetry code: (i) x, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC16H16N4O6
Mr360.33
Crystal system, space groupTriclinic, 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)
V3)827.2 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.16 × 0.14 × 0.10
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.982, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
4365, 3181, 2045
Rint0.062
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.225, 1.02
No. of reflections3181
No. of parameters237
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2—H2A···O10.861.962.593 (3)130
N2—H2A···O1i0.862.273.032 (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

First citationBruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMaliha, B., Hussain, I., Tahir, M. N., Tariq, M. I. & Siddiqui, H. L. (2008). Acta Cryst. E64, o626.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMaliha, B., Tariq, M. I., Tahir, M. N., Hussain, I. & Ali, M. (2009). Acta Cryst. E65, o41.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMancilla, T., Correa-Basurto, J. C., Carbajal, K. S. A., Escalante, E. T. J. S. & Ferrara, J. T. (2007). J. Mex. Chem. Soc. E51, 96–102.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationToru, H., Eiki, N., Ryo, Y. & Shunichi, H. (1986). US Patent No. 4 595 409.  Google Scholar

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