Ethyl 4-benzamido-5-phenyl-4H-1,2,4-triazole-3-carboxyl­ate monohydrate

Wang, L.; Liu, X.-Y.; Wang, P.-A.; Liu, P.; Zhang, S.-Y.

doi:10.1107/S1600536811009998

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o949

doi:10.1107/S1600536811009998

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Ethyl 4-benzamido-5-phenyl-4H-1,2,4-triazole-3-carboxylate monohydrate

Li Wang,^a ^* Xue-Ying Liu,^a Ping-An Wang,^a Peng Liu ^a and Sheng-Yong Zhang ^a

^aDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China
^*Correspondence e-mail: piaolanger@qq.com

(Received 3 March 2011; accepted 17 March 2011; online 23 March 2011)

In the title compound, C₁₈H₁₆N₄O₃·H₂O, the dihedral angles between the triazole ring and the phenyl rings are 84.8 (4) and and 39.8 (4)°. The phenyl rings make a dihedral angle of 84.5 (9)°. In the crystal, the molecules are linked by N—H⋯O and O—H⋯N hydrogen bonds. An intramolecular O⋯N interaction also occurs [2.827 (3) Å]

Related literature

For the synthesis, see: Tadha et al. (1973 ).

Experimental

Crystal data

C₁₈H₁₆N₄O₃·H₂O
M_r = 354.36
Triclinic, $[P \overline 1]$
a = 7.932 (4) Å
b = 8.804 (4) Å
c = 13.316 (6) Å
α = 92.601 (7)°
β = 100.448 (7)°
γ = 91.378 (7)°
V = 913.1 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.33 × 0.28 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS, Bruker, 2001 ) T_min = 0.960, T_max = 0.979
4594 measured reflections
3197 independent reflections
2012 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.210
S = 1.02
3197 reflections
245 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O4ⁱ	0.86	1.99	2.776 (4)	152
O4—H4A⋯N1ⁱⁱ	0.83 (3)	2.17 (3)	2.990 (4)	172 (4)
O4—H4B⋯N2ⁱⁱⁱ	0.82 (3)	2.09 (3)	2.893 (4)	166 (5)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+2; (iii) x-1, y-1, z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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: Mercury (Macrae et al., 2006 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009998/jh2270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009998/jh2270Isup2.hkl

checkCIF report

Comment top

l,2,4 triazole has the widespread biological activity, and it may serve as anticarcinogen, the antiviral drug, the antibacteria reagent, the fungicide,anti-inflammation agent, the analgesic and the antidepressant and so on. Some Synthetic methods had been reported about l,2,4 triazole's, but the synthetic method of the title compound C₁₈H₁₈N₄O₄, (Fig. 1) is reported for the first time. In the title compound there are the intermolecular N4—H···O2 hydrogen bonds and the intramolecular hydrogen bonds between ethyl 5-phenyl-4-[(phenylcarbonyl)amino]-4H-1,2,4-triazole-3-carboxylate and water. The two phenyl rings are twisted away from the plane of the triazole ring by 84.84° and 39.84° respectively. the dihedral angle between two phenyl rings is 84.59°.

Related literature top

For the preparation, see: Tadha et al. (1973).

Experimental top

benzohydrazide (1 equiv.)was dissolved in 100 ml toluene, then methylsulfonic acid (1 equiv.)was dropped into the solution and stirred for 20 minutes. Ethyl 2-chloro-2-oxoacetate (1 equiv.)was added subsequently and heated to reflux for 6 h until the starting material was completely consumed as monitored by TLC. The resultant residue was directly purified by flash chromatography on silica (EtOAc: Cyclohexane 1:1) gave 37% yield as a white solid. recrystallization in ethyl acetate gave fine white crystals suitable for X-ray study.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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: Mercury (Macrae et al., 2006).

Figures top

Fig. 1. Ellipsoid plot

Ethyl 4-benzamido-5-phenyl-4H-1,2,4-triazole-3-carboxylate monohydrate top

Crystal data top

C₁₈H₁₆N₄O₃·H₂O	F(000) = 372
M_r = 354.36	D_x = 1.289 Mg m⁻³
Triclinic, P1	Melting point: 498.450 K
a = 7.932 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.804 (4) Å	Cell parameters from 1073 reflections
c = 13.316 (6) Å	θ = 2.6–23.8°
α = 92.601 (7)°	µ = 0.09 mm⁻¹
β = 100.448 (7)°	T = 296 K
γ = 91.378 (7)°	Block, colorless
V = 913.1 (8) Å³	0.33 × 0.28 × 0.17 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	3197 independent reflections
Radiation source: fine-focus sealed tube	2012 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS, Bruker, 2001)	h = −9→9
T_min = 0.960, T_max = 0.979	k = −8→10
4594 measured reflections	l = −15→15

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.210	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.1284P)²] where P = (F_o² + 2F_c²)/3
3197 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.23 e Å⁻³
2 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₈H₁₆N₄O₃·H₂O	γ = 91.378 (7)°
M_r = 354.36	V = 913.1 (8) Å³
Triclinic, P1	Z = 2
a = 7.932 (4) Å	Mo Kα radiation
b = 8.804 (4) Å	µ = 0.09 mm⁻¹
c = 13.316 (6) Å	T = 296 K
α = 92.601 (7)°	0.33 × 0.28 × 0.17 mm
β = 100.448 (7)°

Data collection top

Bruker APEXII CCD diffractometer	3197 independent reflections
Absorption correction: multi-scan (SADABS, Bruker, 2001)	2012 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.979	R_int = 0.022
4594 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	2 restraints
wR(F²) = 0.210	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.23 e Å⁻³
3197 reflections	Δρ_min = −0.28 e Å⁻³
245 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	0.7002 (3)	0.9462 (3)	0.91869 (17)	0.0571 (6)
N2	0.7312 (3)	1.0778 (3)	0.87158 (17)	0.0560 (6)
N3	0.4588 (3)	1.0142 (2)	0.82616 (16)	0.0465 (6)
N4	0.2941 (3)	1.0037 (2)	0.76763 (16)	0.0477 (6)
H4	0.2113	1.0549	0.7841	0.057*
O1	0.5395 (3)	0.7012 (3)	0.99388 (19)	0.0898 (8)
O2	0.2954 (3)	0.7483 (2)	0.88903 (15)	0.0644 (6)
O3	0.3957 (3)	0.8533 (2)	0.65294 (16)	0.0707 (6)
O4	0.0919 (3)	0.1549 (3)	0.88695 (18)	0.0727 (7)
C1	0.0303 (6)	0.6067 (6)	0.8672 (4)	0.1146 (16)
H1A	−0.0335	0.6930	0.8831	0.172*
H1B	−0.0248	0.5154	0.8840	0.172*
H1C	0.0348	0.6021	0.7956	0.172*
C2	0.2071 (5)	0.6214 (4)	0.9275 (3)	0.0797 (11)
H2A	0.2037	0.6409	0.9993	0.096*
H2B	0.2672	0.5281	0.9200	0.096*
C3	0.4579 (4)	0.7737 (3)	0.9298 (2)	0.0582 (8)
C4	0.5362 (4)	0.9084 (3)	0.88951 (19)	0.0507 (7)
C5	0.5855 (3)	1.1164 (3)	0.81539 (19)	0.0466 (6)
C6	0.5647 (4)	1.2538 (3)	0.75589 (19)	0.0489 (7)
C7	0.6932 (4)	1.2967 (3)	0.7040 (2)	0.0656 (9)
H7	0.7884	1.2369	0.7049	0.079*
C8	0.6797 (5)	1.4283 (4)	0.6510 (3)	0.0772 (10)
H8	0.7663	1.4574	0.6165	0.093*
C9	0.5387 (5)	1.5165 (4)	0.6491 (3)	0.0742 (10)
H9	0.5291	1.6046	0.6128	0.089*
C10	0.4114 (5)	1.4739 (3)	0.7014 (2)	0.0667 (9)
H10	0.3166	1.5343	0.7008	0.080*
C11	0.4232 (4)	1.3429 (3)	0.7545 (2)	0.0572 (8)
H11	0.3366	1.3144	0.7891	0.069*
C12	0.2718 (3)	0.9074 (3)	0.6824 (2)	0.0474 (7)
C13	0.0926 (3)	0.8745 (3)	0.6287 (2)	0.0488 (7)
C14	−0.0503 (4)	0.9134 (4)	0.6671 (2)	0.0704 (9)
H14	−0.0379	0.9633	0.7312	0.084*
C15	−0.2125 (4)	0.8794 (4)	0.6118 (3)	0.0781 (10)
H15	−0.3081	0.9072	0.6389	0.094*
C16	−0.2340 (4)	0.8056 (4)	0.5184 (3)	0.0724 (10)
H16	−0.3435	0.7841	0.4810	0.087*
C17	−0.0927 (5)	0.7635 (5)	0.4803 (3)	0.0898 (12)
H17	−0.1059	0.7109	0.4171	0.108*
C18	0.0701 (4)	0.7985 (4)	0.5351 (2)	0.0730 (9)
H18	0.1654	0.7700	0.5080	0.088*
H4A	0.146 (5)	0.135 (5)	0.9435 (17)	0.107 (15)*
H4B	−0.006 (3)	0.129 (5)	0.893 (4)	0.130 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0410 (14)	0.0673 (15)	0.0602 (14)	0.0028 (11)	0.0004 (10)	0.0077 (12)
N2	0.0393 (14)	0.0667 (15)	0.0608 (14)	−0.0013 (11)	0.0050 (11)	0.0079 (11)
N3	0.0313 (12)	0.0526 (12)	0.0549 (13)	0.0014 (9)	0.0061 (9)	0.0028 (10)
N4	0.0284 (12)	0.0539 (13)	0.0593 (13)	0.0032 (9)	0.0049 (9)	−0.0013 (10)
O1	0.0885 (19)	0.0843 (17)	0.0899 (17)	−0.0041 (14)	−0.0077 (14)	0.0342 (14)
O2	0.0569 (14)	0.0648 (13)	0.0733 (13)	−0.0091 (10)	0.0158 (10)	0.0125 (10)
O3	0.0417 (13)	0.0867 (15)	0.0830 (15)	0.0066 (11)	0.0149 (11)	−0.0199 (11)
O4	0.0421 (14)	0.1099 (18)	0.0658 (15)	0.0039 (13)	0.0110 (11)	−0.0049 (13)
C1	0.083 (3)	0.130 (4)	0.129 (4)	−0.045 (3)	0.016 (3)	0.027 (3)
C2	0.096 (3)	0.068 (2)	0.079 (2)	−0.0244 (19)	0.030 (2)	0.0070 (17)
C3	0.061 (2)	0.0596 (17)	0.0538 (17)	0.0004 (15)	0.0104 (14)	0.0041 (14)
C4	0.0458 (17)	0.0568 (16)	0.0495 (15)	0.0026 (13)	0.0084 (12)	0.0020 (12)
C5	0.0350 (15)	0.0524 (15)	0.0525 (15)	0.0005 (11)	0.0095 (11)	−0.0006 (12)
C6	0.0420 (16)	0.0520 (15)	0.0518 (15)	−0.0037 (12)	0.0081 (12)	−0.0020 (12)
C7	0.053 (2)	0.0646 (19)	0.084 (2)	−0.0015 (15)	0.0245 (16)	0.0067 (16)
C8	0.074 (3)	0.075 (2)	0.089 (2)	−0.0044 (19)	0.0328 (19)	0.0131 (18)
C9	0.092 (3)	0.0573 (18)	0.077 (2)	0.0009 (18)	0.0242 (19)	0.0125 (16)
C10	0.070 (2)	0.0586 (18)	0.073 (2)	0.0077 (15)	0.0145 (16)	0.0022 (15)
C11	0.0530 (19)	0.0556 (16)	0.0637 (17)	−0.0015 (14)	0.0132 (14)	0.0014 (13)
C12	0.0354 (15)	0.0519 (15)	0.0552 (16)	0.0020 (12)	0.0085 (12)	0.0046 (12)
C13	0.0373 (16)	0.0535 (15)	0.0553 (16)	−0.0016 (12)	0.0080 (12)	0.0038 (12)
C14	0.0415 (19)	0.093 (2)	0.073 (2)	−0.0067 (16)	0.0102 (15)	−0.0221 (17)
C15	0.0336 (18)	0.104 (3)	0.096 (3)	−0.0083 (16)	0.0145 (16)	−0.012 (2)
C16	0.045 (2)	0.091 (2)	0.076 (2)	−0.0186 (17)	−0.0027 (16)	0.0062 (18)
C17	0.064 (3)	0.129 (3)	0.066 (2)	−0.018 (2)	−0.0036 (18)	−0.026 (2)
C18	0.053 (2)	0.101 (2)	0.0630 (19)	−0.0017 (17)	0.0133 (15)	−0.0201 (17)

Geometric parameters (Å, º) top

N1—C4	1.319 (4)	C6—C7	1.385 (4)
N1—N2	1.380 (3)	C7—C8	1.380 (4)
N2—C5	1.319 (3)	C7—H7	0.9300
N3—C5	1.364 (3)	C8—C9	1.374 (5)
N3—C4	1.366 (3)	C8—H8	0.9300
N3—N4	1.393 (3)	C9—C10	1.381 (5)
N4—C12	1.368 (3)	C9—H9	0.9300
N4—H4	0.8600	C10—C11	1.376 (4)
O1—C3	1.193 (3)	C10—H10	0.9300
O2—C3	1.314 (4)	C11—H11	0.9300
O2—C2	1.464 (3)	C12—C13	1.486 (4)
O3—C12	1.222 (3)	C13—C18	1.368 (4)
O4—H4A	0.83 (3)	C13—C14	1.371 (4)
O4—H4B	0.82 (3)	C14—C15	1.380 (4)
C1—C2	1.484 (5)	C14—H14	0.9300
C1—H1A	0.9600	C15—C16	1.357 (5)
C1—H1B	0.9600	C15—H15	0.9300
C1—H1C	0.9600	C16—C17	1.364 (5)
C2—H2A	0.9700	C16—H16	0.9300
C2—H2B	0.9700	C17—C18	1.384 (5)
C3—C4	1.491 (4)	C17—H17	0.9300
C5—C6	1.472 (4)	C18—H18	0.9300
C6—C11	1.383 (4)

C4—N1—N2	107.4 (2)	C8—C7—H7	120.0
C5—N2—N1	107.9 (2)	C6—C7—H7	120.0
C5—N3—C4	105.9 (2)	C9—C8—C7	120.1 (3)
C5—N3—N4	125.9 (2)	C9—C8—H8	119.9
C4—N3—N4	126.9 (2)	C7—C8—H8	119.9
C12—N4—N3	116.1 (2)	C8—C9—C10	119.7 (3)
C12—N4—H4	121.9	C8—C9—H9	120.1
N3—N4—H4	121.9	C10—C9—H9	120.1
C3—O2—C2	116.7 (2)	C11—C10—C9	120.7 (3)
H4A—O4—H4B	100 (4)	C11—C10—H10	119.7
C2—C1—H1A	109.5	C9—C10—H10	119.7
C2—C1—H1B	109.5	C10—C11—C6	119.6 (3)
H1A—C1—H1B	109.5	C10—C11—H11	120.2
C2—C1—H1C	109.5	C6—C11—H11	120.2
H1A—C1—H1C	109.5	O3—C12—N4	120.3 (2)
H1B—C1—H1C	109.5	O3—C12—C13	122.7 (3)
O2—C2—C1	107.9 (3)	N4—C12—C13	117.0 (2)
O2—C2—H2A	110.1	C18—C13—C14	118.2 (3)
C1—C2—H2A	110.1	C18—C13—C12	117.3 (3)
O2—C2—H2B	110.1	C14—C13—C12	124.5 (3)
C1—C2—H2B	110.1	C13—C14—C15	120.8 (3)
H2A—C2—H2B	108.4	C13—C14—H14	119.6
O1—C3—O2	125.7 (3)	C15—C14—H14	119.6
O1—C3—C4	121.0 (3)	C16—C15—C14	120.7 (3)
O2—C3—C4	113.3 (2)	C16—C15—H15	119.6
N1—C4—N3	109.5 (2)	C14—C15—H15	119.6
N1—C4—C3	121.3 (3)	C15—C16—C17	119.0 (3)
N3—C4—C3	129.1 (3)	C15—C16—H16	120.5
N2—C5—N3	109.2 (2)	C17—C16—H16	120.5
N2—C5—C6	124.3 (2)	C16—C17—C18	120.4 (3)
N3—C5—C6	126.4 (2)	C16—C17—H17	119.8
C11—C6—C7	119.9 (3)	C18—C17—H17	119.8
C11—C6—C5	121.1 (2)	C13—C18—C17	120.8 (3)
C7—C6—C5	118.9 (3)	C13—C18—H18	119.6
C8—C7—C6	120.0 (3)	C17—C18—H18	119.6

C4—N1—N2—C5	0.1 (3)	N2—C5—C6—C7	40.1 (4)
C5—N3—N4—C12	91.3 (3)	N3—C5—C6—C7	−143.7 (3)
C4—N3—N4—C12	−74.2 (3)	C11—C6—C7—C8	0.0 (4)
C3—O2—C2—C1	−176.4 (3)	C5—C6—C7—C8	−177.5 (3)
C2—O2—C3—O1	1.1 (5)	C6—C7—C8—C9	−0.3 (5)
C2—O2—C3—C4	−177.6 (2)	C7—C8—C9—C10	0.7 (5)
N2—N1—C4—N3	−1.3 (3)	C8—C9—C10—C11	−0.8 (5)
N2—N1—C4—C3	−177.7 (2)	C9—C10—C11—C6	0.4 (5)
C5—N3—C4—N1	1.9 (3)	C7—C6—C11—C10	−0.1 (4)
N4—N3—C4—N1	169.7 (2)	C5—C6—C11—C10	177.3 (2)
C5—N3—C4—C3	177.9 (3)	N3—N4—C12—O3	−10.5 (4)
N4—N3—C4—C3	−14.2 (4)	N3—N4—C12—C13	170.1 (2)
O1—C3—C4—N1	4.2 (5)	O3—C12—C13—C18	−9.5 (4)
O2—C3—C4—N1	−176.9 (3)	N4—C12—C13—C18	169.9 (2)
O1—C3—C4—N3	−171.4 (3)	O3—C12—C13—C14	169.6 (3)
O2—C3—C4—N3	7.5 (4)	N4—C12—C13—C14	−11.0 (4)
N1—N2—C5—N3	1.1 (3)	C18—C13—C14—C15	−1.3 (5)
N1—N2—C5—C6	177.9 (2)	C12—C13—C14—C15	179.6 (3)
C4—N3—C5—N2	−1.8 (3)	C13—C14—C15—C16	0.5 (6)
N4—N3—C5—N2	−169.8 (2)	C14—C15—C16—C17	0.9 (6)
C4—N3—C5—C6	−178.5 (2)	C15—C16—C17—C18	−1.5 (6)
N4—N3—C5—C6	13.5 (4)	C14—C13—C18—C17	0.7 (5)
N2—C5—C6—C11	−137.4 (3)	C12—C13—C18—C17	179.9 (3)
N3—C5—C6—C11	38.9 (4)	C16—C17—C18—C13	0.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O4ⁱ	0.86	1.99	2.776 (4)	152
O4—H4A···N1ⁱⁱ	0.83 (3)	2.17 (3)	2.990 (4)	172 (4)
O4—H4B···N2ⁱⁱⁱ	0.82 (3)	2.09 (3)	2.893 (4)	166 (5)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+2; (iii) x−1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₄O₃·H₂O
M_r	354.36
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.932 (4), 8.804 (4), 13.316 (6)
α, β, γ (°)	92.601 (7), 100.448 (7), 91.378 (7)
V (Å³)	913.1 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.33 × 0.28 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS, Bruker, 2001)
T_min, T_max	0.960, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	4594, 3197, 2012
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.210, 1.02
No. of reflections	3197
No. of parameters	245
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.28

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O4ⁱ	0.86	1.99	2.776 (4)	152
O4—H4A···N1ⁱⁱ	0.83 (3)	2.17 (3)	2.990 (4)	172 (4)
O4—H4B···N2ⁱⁱⁱ	0.82 (3)	2.09 (3)	2.893 (4)	166 (5)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+2; (iii) x−1, y−1, z.

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (20572131).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tadha, V. T. & Srinnivasna, V. R. (1973). Indian J. Chem. 11, 732–734. Google Scholar