1,5-Diphenyl­carbonohydrazide N,N-di­methyl­formamide

Zhang, A.; Ma, S.; Bu, D.

doi:10.1107/S160053681003922X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages o2734-o2735

https://doi.org/10.1107/S160053681003922X

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1,5-Diphenylcarbonohydrazide N,N-dimethylformamide

Ai-yun Zhang,^a ^* Si-yao Ma ^b and Dong Bu ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China, and ^bDepartment of Mathematics, Xi'an University of Architecture and Technology, Xi'an 710055, People's Republic of China
^*Correspondence e-mail: zay@hpu.edu.cn

(Received 14 July 2010; accepted 30 September 2010; online 9 October 2010)

In the title compound, C₁₃H₁₄N₄O·C₃H₇NO, a 1,5-phenylcarbonohydrazide molecule cocrystallizes with an N,N-dimethylformamide molecule. In the 1,5-phenylcarbonohydrazide molecule, the two phenyl rings are twisted by an angle of 45.8 (5)°. Intermolecular N—H⋯O hydrogen bonds and weak intermolecular C—H⋯O interactions contribute to a supramolecular two-dimensional network in the (101) plane.

Related literature

For literature on the applications of 1,5-diphenylcarbonohydrazide, an artificial electron-donor material, see: Verma & Singh (1995 ); Melis et al. (1992 ); Prasad et al. (1991 ); Sundari & Raghavendra (1990 ); Mishra et al. (1993 ). For the structure of diphenylcarbonohydrazide, see: De Ranter et al. (1979 ). For related structures, see: Hamuro et al. (1999 ); Jian et al. (2003 ); Wei et al.(2006 ); Wang et al. (2001 ).

Experimental

Crystal data

C₁₃H₁₄N₄O·C₃H₇NO
M_r = 315.38
Monoclinic, P 2₁ /c
a = 5.9774 (2) Å
b = 14.8531 (6) Å
c = 18.4827 (7) Å
β = 96.029 (3)°
V = 1631.87 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.21 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.982, T_max = 0.984
23310 measured reflections
2902 independent reflections
2061 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.193
S = 1.06
2902 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.13	2.975 (3)	166
C6—H6A⋯O2ⁱⁱ	0.93	2.58	3.370 (4)	143
N2—H2B⋯O1ⁱⁱⁱ	0.86	2.45	3.121 (3)	135
N3—H3B⋯O2	0.86	2.12	2.895 (3)	149
N4—H4B⋯O2ⁱⁱ	0.86	2.31	3.079 (3)	148
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y, z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); 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: https://doi.org/10.1107/S160053681003922X/jj2045sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003922X/jj2045Isup2.hkl

checkCIF report

Comment top

1, 5-diphenylcarbonohydrazide, an artificial electron-donor material, has a variety of applications (Verma & Singh, 1995; Melis et al., 1992; Prasad et al., 1991; Sundari & Raghavendra, 1990; Mishra et al., 1993). The structure of diphenylcarbonohydrazide (C₁₃H₁₄N₄O), (De Ranter et al., 1979) and a number of diphenylcarbonohydrazide derivatives have been prepared (Jian et al., 2003; Wang et al., 2001; Hamuro et al., 1999; Wei et al., 2006).

The title compound, is a co-crystal with a 1,5-phenylcarbonohydrazide molecule and a N, N-dimethylformamide molecule in the unit cell (Fig. 1). In the 1,5-phenylcarbonohydrazide molecule, the dihedral angles of the two benzene rings are twisted by an angle of 45.8 (5)°. The C7/N1/N2/C8 (-91.6 (3)°) and C7/N3/N4/C1 (75.3 (3)°) torsion angles confirm this twist. Crystal packing is dominated by N—H···O hydrogen bonds and weak C—H···O intermolecular interactions (Table 1) which contribute to a supermolecular 2-D network formed in the 101 plane (Fig. 2).

Related literature top

For literature on the applications of 1, 5-diphenylcarbonohydrazide, an artificial electron-donor material, see: Verma & Singh (1995); Melis et al. (1992); Prasad et al. (1991); Sundari & Raghavendra (1990); Mishra et al. (1993). For the structure of diphenylcarbonohydrazide, see: De Ranter, Blaton & Peeters (1979). For related structures, see: Hamuro et al. (1999); Jian et al. (2003); Wei, et al.(2006); Wang, et al. (2001).

Experimental top

A mixture of 1, 5-diphenylcarbazide (0.0233 g), Cd(NO₃)₂(0.0132 g), N, N-dimethylformamide (5 ml), and water (12 ml) was stirred at room temperature for 6 h. The solution was filtered and the filtrate was left to stand undisturbed. Upon slow evaporation at room temperature, the title compound appeared about a month later. The title compound was filtered, washed with water and dried at 298K. The single crystals were grown by slow evaporation of water and N, N-dimethylformamide in the filtered mixture of 1, 5-diphenylcarbazide, Cd(NO₃)₂, N, N-dimethylformamide, and water at 298K.

Structure description top

For literature on the applications of 1, 5-diphenylcarbonohydrazide, an artificial electron-donor material, see: Verma & Singh (1995); Melis et al. (1992); Prasad et al. (1991); Sundari & Raghavendra (1990); Mishra et al. (1993). For the structure of diphenylcarbonohydrazide, see: De Ranter, Blaton & Peeters (1979). For related structures, see: Hamuro et al. (1999); Jian et al. (2003); Wei, et al.(2006); Wang, et al. (2001).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 compound, C₁₆H₂₁N₅O₂, showing the atom-labeling scheme with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing diagram for the title compound viewed down the b axis. Dashed lines indicate N—H···O and C—H···O hydrogen bonds forming an infinite two-dimensional polymeric chain along the a axis.

1,5-Diphenylcarbonohydrazide N,N-dimethylformamide top

Crystal data top

C₁₃H₁₄N₄O·C₃H₇NO	F(000) = 672
M_r = 315.38	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3501 reflections
a = 5.9774 (2) Å	θ = 2.6–21.5°
b = 14.8531 (6) Å	µ = 0.09 mm⁻¹
c = 18.4827 (7) Å	T = 296 K
β = 96.029 (3)°	Block, colorless
V = 1631.87 (11) Å³	0.21 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2902 independent reflections
Radiation source: fine-focus sealed tube	2061 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 25.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −7→7
T_min = 0.982, T_max = 0.984	k = −17→17
23310 measured reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.193	w = 1/[σ²(F_o²) + (0.1085P)² + 0.5441P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2902 reflections	Δρ_max = 0.32 e Å⁻³
209 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

Crystal data top

C₁₃H₁₄N₄O·C₃H₇NO	V = 1631.87 (11) Å³
M_r = 315.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.9774 (2) Å	µ = 0.09 mm⁻¹
b = 14.8531 (6) Å	T = 296 K
c = 18.4827 (7) Å	0.21 × 0.20 × 0.18 mm
β = 96.029 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2902 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2061 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.984	R_int = 0.049
23310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.193	H-atom parameters constrained
S = 1.06	Δρ_max = 0.32 e Å⁻³
2902 reflections	Δρ_min = −0.36 e Å⁻³
209 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.4510 (4)	0.55844 (17)	0.25962 (14)	0.0456 (6)
C2	0.6356 (5)	0.5015 (2)	0.26959 (15)	0.0573 (8)
H2A	0.7563	0.5097	0.2423	0.069*
C3	0.6407 (5)	0.4328 (2)	0.31971 (17)	0.0633 (8)
H3A	0.7645	0.3946	0.3256	0.076*
C4	0.4651 (5)	0.4197 (2)	0.36131 (16)	0.0639 (8)
H4A	0.4689	0.3728	0.3947	0.077*
C5	0.2840 (5)	0.4774 (2)	0.35257 (16)	0.0608 (8)
H5A	0.1658	0.4698	0.3809	0.073*
C6	0.2757 (4)	0.54590 (18)	0.30260 (15)	0.0509 (7)
H6A	0.1521	0.5842	0.2974	0.061*
C7	0.5425 (4)	0.57813 (16)	0.09720 (13)	0.0401 (6)
C8	0.8908 (4)	0.71277 (16)	0.02790 (12)	0.0396 (6)
C9	0.6983 (4)	0.74404 (19)	−0.01259 (15)	0.0518 (7)
H9A	0.5677	0.7095	−0.0165	0.062*
C10	0.7002 (5)	0.8262 (2)	−0.04697 (17)	0.0646 (8)
H10A	0.5706	0.8467	−0.0742	0.078*
C11	0.8908 (5)	0.8785 (2)	−0.04161 (17)	0.0665 (9)
H11A	0.8907	0.9339	−0.0650	0.080*
C12	1.0807 (5)	0.8478 (2)	−0.00140 (17)	0.0637 (8)
H12A	1.2104	0.8828	0.0023	0.076*
C13	1.0828 (4)	0.76617 (19)	0.03362 (15)	0.0506 (7)
H13A	1.2129	0.7466	0.0612	0.061*
C14	0.9098 (5)	0.78263 (19)	0.25852 (16)	0.0550 (7)
H14A	0.7616	0.8000	0.2453	0.066*
C15	0.9162 (6)	0.8990 (2)	0.34963 (18)	0.0675 (9)
H15A	1.0221	0.9236	0.3871	0.101*
H15B	0.7887	0.8755	0.3710	0.101*
H15C	0.8675	0.9454	0.3154	0.101*
C16	1.2467 (5)	0.8018 (2)	0.33949 (17)	0.0656 (8)
H16A	1.3015	0.8413	0.3785	0.098*
H16B	1.3423	0.8060	0.3010	0.098*
H16C	1.2467	0.7410	0.3571	0.098*
N1	0.7115 (3)	0.57302 (14)	0.05309 (11)	0.0445 (5)
H1A	0.7038	0.5346	0.0181	0.053*
N2	0.8964 (3)	0.63018 (13)	0.06480 (11)	0.0437 (5)
H2B	1.0117	0.6151	0.0941	0.052*
N3	0.5839 (4)	0.63150 (15)	0.15609 (11)	0.0510 (6)
H3B	0.6994	0.6664	0.1597	0.061*
N4	0.4411 (4)	0.63076 (15)	0.21120 (12)	0.0536 (6)
H4B	0.3483	0.6743	0.2152	0.064*
N5	1.0222 (3)	0.82726 (15)	0.31247 (11)	0.0483 (6)
O1	0.3662 (3)	0.53634 (12)	0.08206 (10)	0.0491 (5)
O2	0.9826 (3)	0.72042 (14)	0.22424 (12)	0.0664 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0427 (14)	0.0537 (16)	0.0404 (14)	−0.0021 (11)	0.0043 (11)	−0.0108 (11)
C2	0.0430 (15)	0.073 (2)	0.0570 (17)	0.0041 (13)	0.0103 (13)	−0.0061 (15)
C3	0.0531 (17)	0.076 (2)	0.0592 (18)	0.0144 (14)	−0.0027 (14)	0.0009 (15)
C4	0.0681 (19)	0.0691 (19)	0.0538 (17)	−0.0009 (16)	0.0025 (15)	0.0077 (15)
C5	0.0565 (17)	0.072 (2)	0.0562 (17)	−0.0062 (15)	0.0179 (14)	−0.0011 (15)
C6	0.0445 (15)	0.0541 (16)	0.0558 (16)	0.0024 (12)	0.0129 (12)	−0.0057 (13)
C7	0.0391 (13)	0.0404 (13)	0.0411 (13)	−0.0030 (10)	0.0052 (10)	0.0033 (10)
C8	0.0367 (13)	0.0462 (14)	0.0367 (13)	−0.0037 (10)	0.0078 (10)	−0.0056 (10)
C9	0.0366 (14)	0.0610 (17)	0.0564 (16)	−0.0053 (12)	−0.0023 (12)	0.0045 (13)
C10	0.0560 (18)	0.071 (2)	0.0651 (19)	0.0068 (15)	−0.0035 (14)	0.0140 (15)
C11	0.073 (2)	0.0569 (18)	0.069 (2)	−0.0022 (15)	0.0072 (16)	0.0169 (15)
C12	0.0573 (18)	0.0631 (19)	0.071 (2)	−0.0181 (14)	0.0092 (15)	0.0067 (16)
C13	0.0392 (14)	0.0584 (17)	0.0536 (16)	−0.0074 (12)	0.0012 (12)	0.0020 (13)
C14	0.0434 (15)	0.0590 (17)	0.0609 (17)	0.0041 (13)	−0.0024 (13)	0.0002 (14)
C15	0.084 (2)	0.0539 (17)	0.0676 (19)	0.0083 (16)	0.0240 (17)	−0.0042 (15)
C16	0.0593 (18)	0.072 (2)	0.0623 (18)	0.0048 (15)	−0.0112 (15)	−0.0066 (15)
N1	0.0410 (11)	0.0466 (12)	0.0468 (12)	−0.0116 (9)	0.0092 (9)	−0.0087 (9)
N2	0.0345 (10)	0.0501 (13)	0.0453 (12)	−0.0064 (9)	−0.0018 (9)	0.0027 (9)
N3	0.0486 (13)	0.0596 (14)	0.0468 (12)	−0.0145 (10)	0.0146 (10)	−0.0109 (10)
N4	0.0550 (13)	0.0573 (14)	0.0512 (13)	0.0062 (11)	0.0181 (11)	−0.0043 (11)
N5	0.0454 (12)	0.0487 (13)	0.0503 (13)	0.0043 (10)	0.0024 (10)	−0.0043 (10)
O1	0.0416 (10)	0.0540 (11)	0.0520 (11)	−0.0122 (8)	0.0061 (8)	−0.0046 (8)
O2	0.0627 (13)	0.0650 (13)	0.0687 (13)	0.0034 (10)	−0.0060 (10)	−0.0200 (11)

Geometric parameters (Å, º) top

C1—C2	1.388 (4)	C11—C12	1.368 (4)
C1—C6	1.392 (3)	C11—H11A	0.9300
C1—N4	1.395 (3)	C12—C13	1.374 (4)
C2—C3	1.376 (4)	C12—H12A	0.9300
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.378 (4)	C14—O2	1.226 (3)
C3—H3A	0.9300	C14—N5	1.321 (4)
C4—C5	1.376 (4)	C14—H14A	0.9300
C4—H4A	0.9300	C15—N5	1.449 (3)
C5—C6	1.371 (4)	C15—H15A	0.9600
C5—H5A	0.9300	C15—H15B	0.9600
C6—H6A	0.9300	C15—H15C	0.9600
C7—O1	1.230 (3)	C16—N5	1.433 (4)
C7—N3	1.348 (3)	C16—H16A	0.9600
C7—N1	1.365 (3)	C16—H16B	0.9600
C8—C13	1.390 (4)	C16—H16C	0.9600
C8—C9	1.385 (4)	N1—N2	1.392 (3)
C8—N2	1.402 (3)	N1—H1A	0.8600
C9—C10	1.377 (4)	N2—H2B	0.8600
C9—H9A	0.9300	N3—N4	1.396 (3)
C10—C11	1.373 (4)	N3—H3B	0.8600
C10—H10A	0.9300	N4—H4B	0.8600

C2—C1—C6	118.6 (3)	C13—C12—H12A	119.5
C2—C1—N4	122.3 (2)	C12—C13—C8	120.1 (3)
C6—C1—N4	119.0 (2)	C12—C13—H13A	120.0
C3—C2—C1	120.2 (3)	C8—C13—H13A	120.0
C3—C2—H2A	119.9	O2—C14—N5	126.0 (3)
C1—C2—H2A	119.9	O2—C14—H14A	117.0
C4—C3—C2	121.0 (3)	N5—C14—H14A	117.0
C4—C3—H3A	119.5	N5—C15—H15A	109.5
C2—C3—H3A	119.5	N5—C15—H15B	109.5
C5—C4—C3	118.9 (3)	H15A—C15—H15B	109.5
C5—C4—H4A	120.6	N5—C15—H15C	109.5
C3—C4—H4A	120.6	H15A—C15—H15C	109.5
C6—C5—C4	120.9 (3)	H15B—C15—H15C	109.5
C6—C5—H5A	119.6	N5—C16—H16A	109.5
C4—C5—H5A	119.6	N5—C16—H16B	109.5
C5—C6—C1	120.5 (3)	H16A—C16—H16B	109.5
C5—C6—H6A	119.8	N5—C16—H16C	109.5
C1—C6—H6A	119.8	H16A—C16—H16C	109.5
O1—C7—N3	124.1 (2)	H16B—C16—H16C	109.5
O1—C7—N1	120.4 (2)	C7—N1—N2	119.9 (2)
N3—C7—N1	115.5 (2)	C7—N1—H1A	120.1
C13—C8—C9	118.8 (2)	N2—N1—H1A	120.1
C13—C8—N2	119.0 (2)	N1—N2—C8	118.7 (2)
C9—C8—N2	122.2 (2)	N1—N2—H2B	120.7
C10—C9—C8	120.0 (3)	C8—N2—H2B	120.7
C10—C9—H9A	120.0	C7—N3—N4	120.7 (2)
C8—C9—H9A	120.0	C7—N3—H3B	119.7
C11—C10—C9	121.0 (3)	N4—N3—H3B	119.7
C11—C10—H10A	119.5	N3—N4—C1	119.1 (2)
C9—C10—H10A	119.5	N3—N4—H4B	120.5
C10—C11—C12	119.1 (3)	C1—N4—H4B	120.5
C10—C11—H11A	120.5	C14—N5—C16	120.9 (2)
C12—C11—H11A	120.5	C14—N5—C15	120.9 (2)
C11—C12—C13	121.0 (3)	C16—N5—C15	118.0 (2)
C11—C12—H12A	119.5

C6—C1—C2—C3	1.7 (4)	C9—C8—C13—C12	−0.9 (4)
N4—C1—C2—C3	177.9 (3)	N2—C8—C13—C12	−179.3 (2)
C1—C2—C3—C4	−0.7 (5)	O1—C7—N1—N2	170.8 (2)
C2—C3—C4—C5	−0.7 (5)	N3—C7—N1—N2	−8.7 (3)
C3—C4—C5—C6	1.0 (5)	C7—N1—N2—C8	−91.6 (3)
C4—C5—C6—C1	0.0 (4)	C13—C8—N2—N1	−173.7 (2)
C2—C1—C6—C5	−1.4 (4)	C9—C8—N2—N1	8.1 (3)
N4—C1—C6—C5	−177.7 (3)	O1—C7—N3—N4	11.1 (4)
C13—C8—C9—C10	0.7 (4)	N1—C7—N3—N4	−169.4 (2)
N2—C8—C9—C10	179.0 (2)	C7—N3—N4—C1	75.3 (3)
C8—C9—C10—C11	−0.3 (4)	C2—C1—N4—N3	19.4 (4)
C9—C10—C11—C12	0.0 (5)	C6—C1—N4—N3	−164.4 (2)
C10—C11—C12—C13	−0.2 (5)	O2—C14—N5—C16	−3.8 (5)
C11—C12—C13—C8	0.7 (4)	O2—C14—N5—C15	−179.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.13	2.975 (3)	166
C6—H6A···O2ⁱⁱ	0.93	2.58	3.370 (4)	143
N2—H2B···O1ⁱⁱⁱ	0.86	2.45	3.121 (3)	135
N3—H3B···O2	0.86	2.12	2.895 (3)	149
N4—H4B···O2ⁱⁱ	0.86	2.31	3.079 (3)	148

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₄O·C₃H₇NO
M_r	315.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.9774 (2), 14.8531 (6), 18.4827 (7)
β (°)	96.029 (3)
V (Å³)	1631.87 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.21 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.982, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	23310, 2902, 2061
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.193, 1.06
No. of reflections	2902
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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
N1—H1A···O1ⁱ	0.86	2.13	2.975 (3)	166.0
C6—H6A···O2ⁱⁱ	0.93	2.58	3.370 (4)	143.0
N2—H2B···O1ⁱⁱⁱ	0.86	2.45	3.121 (3)	135.3
N3—H3B···O2	0.86	2.12	2.895 (3)	149.1
N4—H4B···O2ⁱⁱ	0.86	2.31	3.079 (3)	148.4

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) x+1, y, z.

Acknowledgements

The authors thank the Universities and Colleges Natural Science Foundation of Henan (grant No. 2009 A150011) and the Natural Science Foundation of China (grant No. 200903036).

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