2-Amino-1H-benzoimidazol-3-ium 4,4,4-trifluoro-1,3-dioxo-1-phenyl­butan-2-ide

Li, G.-C.; Yang, F.-L.; Yao, C.-S.

doi:10.1107/S1600536808037483

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2460

doi:10.1107/S1600536808037483

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2-Amino-1H-benzoimidazol-3-ium 4,4,4-trifluoro-1,3-dioxo-1-phenylbutan-2-ide

Gong-Chun Li,^a ^* Feng-Ling Yang ^a and Chang-Sheng Yao ^b

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, and Key Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: actaeli@mail.google.com

(Received 12 October 2008; accepted 12 November 2008; online 26 November 2008)

In the title compound, C₇H₈N₃⁺·C₁₀H₆F₃O₂⁻, 1H-benzoimidazol-2-amine system adopts a planar conformation with an r.m.s. deviation of 0.0174 Å. The cation and anion in the asymmetric unit are linked by N—H⋯O hydrogen bonds. There are also additional intermolecular N—H⋯O hydrogen bonds and π–π stacking interactions between the phenyl rings of neighbouring anions with centroid–centroid distances of 4.0976 (13) Å.

Related literature

For details of the bioactivity of organofluorine compounds, see: Hermann et al. (2003 ); Ulrich (2004 ).

Experimental

Crystal data

C₇H₈N₃⁺·C₁₀H₆F₃O₂⁻
M_r = 349.31
Orthorhombic, P b c a
a = 16.755 (3) Å
b = 10.552 (2) Å
c = 18.497 (4) Å
V = 3270.0 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 113 (2) K
0.12 × 0.10 × 0.06 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002 ) T_min = 0.986, T_max = 0.993
31132 measured reflections
2881 independent reflections
2609 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.107
S = 1.06
2881 reflections
243 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.877 (9)	2.004 (11)	2.7803 (18)	146.8 (16)
N3—H3A⋯O1ⁱ	0.895 (9)	1.949 (13)	2.7651 (17)	150.9 (19)
N3—H3A⋯O2ⁱ	0.895 (9)	2.363 (18)	2.9912 (18)	127.3 (17)
N1—H1B⋯O1	0.879 (9)	2.030 (10)	2.8662 (18)	158.4 (16)
N2—H2A⋯O2	0.905 (10)	1.862 (11)	2.7360 (18)	161.8 (19)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536808037483/sj2549sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037483/sj2549Isup2.hkl

checkCIF report

Comment top

Compounds that contain fluorine exhibit particular bioactivity, for example, flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich,2004). This led us to pay much attention to the synthesis and structure of similar fluoro-compounds. During the synthesis of trifluoromethylated heterocyclic compounds, an intermediate, the title compound,(I), Fig.1, was isolated and we report its crystal structure here.

The 1H-benzo[d]imizol-2-amine cation adopts a planar conformation with an rms deviation of 0.0174 for the fitted atoms. The phenyl ring is almost perpendicular to the fused heterocyclic rings, with a dihedral angle of 81.84 (4)° between them. The cation and anion in the asymmetric unit are linked by N1—H1B···O1 and N2—H2A···O2 hydrogen bonds.

The crystal packing is further stabilized by additional intermolecular N—H···O hydrogen bonds (Table 1, Fig. 2) and intermolecular π···π stacking interactions between the C5-C10 phenyl rings (symmetry code: 2-x, -y, -z) of neighbouring anions with centroid-to-centroid distances, plane-plane distances and displacement distances of 4.0976 (13), 3.786 and 1.565Å respectively.

Related literature top

For details of the bioactivity of organofluorine compounds, see: Hermann et al. (2003); Ulrich (2004).

Experimental top

The title compound was synthesized by the reaction of 4,4,4-trifluoro-1- phenylbutane-1,3-dione (1 mmol) and 1H-benzo[d]imidazol-2-amine (1 mmol) in refluxing ethanol (20 mL) for a certain time (monitored by TLC). Cooling, the reaction mixture slowly to room temperature, gave single crystals suitable for X-ray diffraction.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear (Rigaku/MSC, 2002); data reduction: CrystalClear (Rigaku/MSC, 2002); 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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen bonds are drawn as dashed lines.
	Fig. 2. The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

2-Amino-1H-benzoimidazol-3-ium 4,4,4-trifluoro-1,3-dioxo-1-phenylbutan-2-ide top

Crystal data top

C₇H₈N₃⁺·C₁₀H₆F₃O₂⁻	F(000) = 1440
M_r = 349.31	D_x = 1.419 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6974 reflections
a = 16.755 (3) Å	θ = 2.2–27.9°
b = 10.552 (2) Å	µ = 0.12 mm⁻¹
c = 18.497 (4) Å	T = 113 K
V = 3270.0 (11) Å³	Block, yellow
Z = 8	0.12 × 0.10 × 0.06 mm

Data collection top

Rigaku Saturn CCD diffractometer	2881 independent reflections
Radiation source: rotating anode	2609 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.050
ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	h = −19→19
T_min = 0.986, T_max = 0.993	k = −12→12
31132 measured reflections	l = −22→21

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0613P)² + 0.895P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2881 reflections	Δρ_max = 0.21 e Å⁻³
243 parameters	Δρ_min = −0.20 e Å⁻³
5 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: 0.0073 (10)

Crystal data top

C₇H₈N₃⁺·C₁₀H₆F₃O₂⁻	V = 3270.0 (11) Å³
M_r = 349.31	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.755 (3) Å	µ = 0.12 mm⁻¹
b = 10.552 (2) Å	T = 113 K
c = 18.497 (4) Å	0.12 × 0.10 × 0.06 mm

Data collection top

Rigaku Saturn CCD diffractometer	2881 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	2609 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.993	R_int = 0.050
31132 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	5 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.21 e Å⁻³
2881 reflections	Δρ_min = −0.20 e Å⁻³
243 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 > 2sigma(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
F1	0.74257 (7)	0.54639 (12)	0.05657 (5)	0.0552 (3)
F2	0.77552 (6)	0.66729 (9)	0.14532 (6)	0.0473 (3)
F3	0.71669 (6)	0.49082 (11)	0.16580 (6)	0.0467 (3)
O1	1.01117 (6)	0.37243 (10)	0.11875 (6)	0.0301 (3)
O2	0.88568 (6)	0.49842 (10)	0.19269 (6)	0.0303 (3)
N1	1.03832 (8)	0.19158 (15)	0.23172 (8)	0.0379 (4)
N2	0.90662 (8)	0.26462 (13)	0.25377 (7)	0.0298 (3)
N3	0.94668 (8)	0.09546 (13)	0.31266 (7)	0.0295 (3)
C1	0.77211 (10)	0.54628 (16)	0.12397 (9)	0.0335 (4)
C2	0.85307 (9)	0.48052 (14)	0.13136 (8)	0.0277 (3)
C3	0.88043 (9)	0.40780 (15)	0.07420 (8)	0.0290 (4)
H3	0.8467	0.3955	0.0349	0.035*
C4	0.95774 (9)	0.35055 (14)	0.07232 (8)	0.0264 (3)
C5	0.97828 (9)	0.26266 (14)	0.01141 (8)	0.0263 (3)
C6	1.05759 (10)	0.25313 (16)	−0.01066 (9)	0.0324 (4)
H6	1.0962	0.3030	0.0116	0.039*
C7	1.07968 (10)	0.17084 (17)	−0.06508 (10)	0.0378 (4)
H7	1.1327	0.1665	−0.0797	0.045*
C8	1.02270 (11)	0.09443 (16)	−0.09797 (9)	0.0368 (4)
H8	1.0376	0.0379	−0.1341	0.044*
C9	0.94389 (10)	0.10278 (15)	−0.07679 (9)	0.0346 (4)
H9	0.9057	0.0518	−0.0989	0.042*
C10	0.92111 (10)	0.18696 (15)	−0.02263 (8)	0.0308 (4)
H10	0.8678	0.1928	−0.0091	0.037*
C11	0.96806 (9)	0.18451 (15)	0.26443 (8)	0.0296 (4)
C12	0.84329 (9)	0.22790 (15)	0.29854 (8)	0.0275 (4)
C13	0.76879 (9)	0.28105 (17)	0.31021 (8)	0.0321 (4)
H13	0.7518	0.3527	0.2853	0.038*
C14	0.72078 (10)	0.22158 (17)	0.36124 (9)	0.0349 (4)
H14	0.6705	0.2548	0.3710	0.042*
C15	0.74579 (10)	0.11347 (17)	0.39833 (9)	0.0339 (4)
H15	0.7118	0.0763	0.4319	0.041*
C16	0.82038 (10)	0.06027 (15)	0.38614 (8)	0.0309 (4)
H16	0.8371	−0.0120	0.4106	0.037*
C17	0.86862 (9)	0.11999 (14)	0.33575 (8)	0.0273 (3)
H1A	1.0783 (9)	0.1439 (16)	0.2457 (10)	0.046 (5)*
H1B	1.0438 (10)	0.2461 (14)	0.1961 (8)	0.043 (5)*
H2A	0.9093 (12)	0.3377 (13)	0.2283 (10)	0.051 (6)*
H3A	0.9769 (11)	0.0317 (15)	0.3290 (11)	0.051 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0509 (7)	0.0792 (8)	0.0356 (6)	0.0313 (6)	−0.0129 (5)	−0.0053 (6)
F2	0.0462 (6)	0.0331 (6)	0.0628 (7)	0.0093 (4)	0.0013 (5)	−0.0034 (5)
F3	0.0293 (5)	0.0561 (7)	0.0546 (7)	−0.0022 (5)	0.0024 (5)	0.0043 (5)
O1	0.0292 (6)	0.0319 (6)	0.0291 (6)	−0.0017 (5)	−0.0052 (5)	−0.0008 (5)
O2	0.0307 (6)	0.0322 (6)	0.0279 (6)	−0.0019 (5)	−0.0042 (4)	−0.0015 (5)
N1	0.0316 (8)	0.0461 (9)	0.0358 (8)	0.0102 (7)	0.0039 (6)	0.0122 (7)
N2	0.0306 (7)	0.0313 (7)	0.0274 (7)	0.0048 (6)	−0.0006 (5)	0.0055 (6)
N3	0.0298 (7)	0.0304 (7)	0.0284 (7)	0.0056 (6)	−0.0008 (5)	0.0029 (6)
C1	0.0353 (9)	0.0355 (9)	0.0296 (8)	0.0026 (7)	−0.0016 (7)	0.0005 (7)
C2	0.0275 (8)	0.0253 (8)	0.0301 (8)	−0.0030 (6)	−0.0033 (6)	0.0048 (6)
C3	0.0295 (8)	0.0312 (8)	0.0263 (8)	0.0009 (6)	−0.0056 (6)	0.0006 (6)
C4	0.0296 (8)	0.0239 (8)	0.0256 (7)	−0.0038 (6)	−0.0027 (6)	0.0053 (6)
C5	0.0291 (8)	0.0251 (7)	0.0249 (7)	−0.0002 (6)	−0.0030 (6)	0.0044 (6)
C6	0.0285 (8)	0.0337 (9)	0.0350 (9)	−0.0024 (7)	−0.0036 (7)	−0.0011 (7)
C7	0.0309 (9)	0.0418 (10)	0.0407 (9)	0.0010 (7)	0.0045 (7)	−0.0035 (8)
C8	0.0452 (10)	0.0324 (9)	0.0327 (9)	0.0025 (7)	0.0014 (7)	−0.0036 (7)
C9	0.0391 (9)	0.0286 (8)	0.0360 (9)	−0.0057 (7)	−0.0058 (7)	−0.0025 (7)
C10	0.0287 (8)	0.0306 (8)	0.0330 (8)	−0.0030 (6)	−0.0021 (6)	0.0020 (7)
C11	0.0301 (9)	0.0336 (8)	0.0250 (8)	0.0036 (7)	−0.0028 (6)	0.0009 (6)
C12	0.0293 (8)	0.0305 (8)	0.0227 (7)	−0.0001 (6)	−0.0027 (6)	−0.0021 (6)
C13	0.0300 (9)	0.0369 (9)	0.0292 (8)	0.0055 (7)	−0.0047 (6)	−0.0011 (7)
C14	0.0260 (8)	0.0453 (10)	0.0332 (9)	0.0007 (7)	−0.0029 (6)	−0.0045 (8)
C15	0.0300 (8)	0.0421 (10)	0.0298 (8)	−0.0074 (7)	−0.0005 (7)	−0.0015 (7)
C16	0.0348 (9)	0.0300 (8)	0.0279 (8)	−0.0032 (7)	−0.0049 (6)	0.0018 (6)
C17	0.0279 (8)	0.0290 (8)	0.0249 (7)	0.0008 (6)	−0.0056 (6)	−0.0033 (6)

Geometric parameters (Å, º) top

F1—C1	1.3415 (19)	C5—C10	1.397 (2)
F2—C1	1.338 (2)	C6—C7	1.380 (2)
F3—C1	1.3429 (19)	C6—H6	0.9300
O1—C4	1.2618 (18)	C7—C8	1.390 (3)
O2—C2	1.2732 (18)	C7—H7	0.9300
N1—C11	1.326 (2)	C8—C9	1.380 (2)
N1—H1A	0.877 (9)	C8—H8	0.9300
N1—H1B	0.879 (9)	C9—C10	1.392 (2)
N2—C11	1.346 (2)	C9—H9	0.9300
N2—C12	1.401 (2)	C10—H10	0.9300
N2—H2A	0.905 (10)	C12—C13	1.385 (2)
N3—C11	1.344 (2)	C12—C17	1.396 (2)
N3—C17	1.400 (2)	C13—C14	1.390 (2)
N3—H3A	0.895 (9)	C13—H13	0.9300
C1—C2	1.530 (2)	C14—C15	1.395 (2)
C2—C3	1.385 (2)	C14—H14	0.9300
C3—C4	1.430 (2)	C15—C16	1.388 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.499 (2)	C16—C17	1.385 (2)
C5—C6	1.394 (2)	C16—H16	0.9300

C11—N1—H1A	120.8 (12)	C8—C7—H7	120.0
C11—N1—H1B	118.1 (11)	C9—C8—C7	119.73 (16)
H1A—N1—H1B	121.1 (14)	C9—C8—H8	120.1
C11—N2—C12	108.60 (13)	C7—C8—H8	120.1
C11—N2—H2A	125.0 (13)	C8—C9—C10	120.49 (15)
C12—N2—H2A	125.5 (13)	C8—C9—H9	119.8
C11—N3—C17	108.79 (13)	C10—C9—H9	119.8
C11—N3—H3A	126.8 (14)	C9—C10—C5	120.07 (15)
C17—N3—H3A	124.4 (14)	C9—C10—H10	120.0
F2—C1—F1	106.81 (13)	C5—C10—H10	120.0
F2—C1—F3	105.99 (13)	N1—C11—N3	125.36 (14)
F1—C1—F3	106.30 (13)	N1—C11—N2	125.23 (15)
F2—C1—C2	111.64 (13)	N3—C11—N2	109.40 (14)
F1—C1—C2	114.24 (14)	C13—C12—C17	121.81 (14)
F3—C1—C2	111.35 (13)	C13—C12—N2	131.50 (15)
O2—C2—C3	128.36 (14)	C17—C12—N2	106.66 (13)
O2—C2—C1	113.13 (14)	C12—C13—C14	116.39 (15)
C3—C2—C1	118.47 (14)	C12—C13—H13	121.8
C2—C3—C4	123.55 (14)	C14—C13—H13	121.8
C2—C3—H3	118.2	C13—C14—C15	121.95 (15)
C4—C3—H3	118.2	C13—C14—H14	119.0
O1—C4—C3	123.29 (14)	C15—C14—H14	119.0
O1—C4—C5	117.51 (13)	C16—C15—C14	121.39 (15)
C3—C4—C5	119.18 (13)	C16—C15—H15	119.3
C6—C5—C10	118.71 (14)	C14—C15—H15	119.3
C6—C5—C4	118.92 (13)	C17—C16—C15	116.78 (15)
C10—C5—C4	122.34 (14)	C17—C16—H16	121.6
C7—C6—C5	120.98 (15)	C15—C16—H16	121.6
C7—C6—H6	119.5	C16—C17—C12	121.68 (14)
C5—C6—H6	119.5	C16—C17—N3	131.78 (14)
C6—C7—C8	120.01 (16)	C12—C17—N3	106.52 (13)
C6—C7—H7	120.0

F2—C1—C2—O2	48.38 (18)	C4—C5—C10—C9	−177.14 (14)
F1—C1—C2—O2	169.71 (14)	C17—N3—C11—N1	179.40 (15)
F3—C1—C2—O2	−69.86 (17)	C17—N3—C11—N2	−1.38 (17)
F2—C1—C2—C3	−133.69 (15)	C12—N2—C11—N1	−179.13 (15)
F1—C1—C2—C3	−12.4 (2)	C12—N2—C11—N3	1.64 (18)
F3—C1—C2—C3	108.07 (16)	C11—N2—C12—C13	177.01 (16)
O2—C2—C3—C4	−7.8 (3)	C11—N2—C12—C17	−1.26 (17)
C1—C2—C3—C4	174.64 (14)	C17—C12—C13—C14	0.3 (2)
C2—C3—C4—O1	−8.1 (2)	N2—C12—C13—C14	−177.71 (16)
C2—C3—C4—C5	173.70 (14)	C12—C13—C14—C15	−0.6 (2)
O1—C4—C5—C6	−27.7 (2)	C13—C14—C15—C16	0.3 (2)
C3—C4—C5—C6	150.58 (15)	C14—C15—C16—C17	0.3 (2)
O1—C4—C5—C10	150.25 (14)	C15—C16—C17—C12	−0.5 (2)
C3—C4—C5—C10	−31.4 (2)	C15—C16—C17—N3	177.26 (15)
C10—C5—C6—C7	0.1 (2)	C13—C12—C17—C16	0.2 (2)
C4—C5—C6—C7	178.13 (15)	N2—C12—C17—C16	178.68 (14)
C5—C6—C7—C8	−1.0 (3)	C13—C12—C17—N3	−178.06 (14)
C6—C7—C8—C9	1.1 (3)	N2—C12—C17—N3	0.42 (16)
C7—C8—C9—C10	−0.1 (3)	C11—N3—C17—C16	−177.45 (16)
C8—C9—C10—C5	−0.8 (2)	C11—N3—C17—C12	0.57 (16)
C6—C5—C10—C9	0.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.88 (1)	2.00 (1)	2.7803 (18)	147 (2)
N3—H3A···O1ⁱ	0.90 (1)	1.95 (1)	2.7651 (17)	151 (2)
N3—H3A···O2ⁱ	0.90 (1)	2.36 (2)	2.9912 (18)	127 (2)
N1—H1B···O1	0.88 (1)	2.03 (1)	2.8662 (18)	158 (2)
N2—H2A···O2	0.91 (1)	1.86 (1)	2.7360 (18)	162 (2)

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

Experimental details

Crystal data
Chemical formula	C₇H₈N₃⁺·C₁₀H₆F₃O₂⁻
M_r	349.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	113
a, b, c (Å)	16.755 (3), 10.552 (2), 18.497 (4)
V (Å³)	3270.0 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2002)
T_min, T_max	0.986, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	31132, 2881, 2609
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.107, 1.06
No. of reflections	2881
No. of parameters	243
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: CrystalClear (Rigaku/MSC, 2002), 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···O2ⁱ	0.877 (9)	2.004 (11)	2.7803 (18)	146.8 (16)
N3—H3A···O1ⁱ	0.895 (9)	1.949 (13)	2.7651 (17)	150.9 (19)
N3—H3A···O2ⁱ	0.895 (9)	2.363 (18)	2.9912 (18)	127.3 (17)
N1—H1B···O1	0.879 (9)	2.030 (10)	2.8662 (18)	158.4 (16)
N2—H2A···O2	0.905 (10)	1.862 (11)	2.7360 (18)	161.8 (19)

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

Acknowledgements

The authors thank the Natural Science Foundation of Henan Province, China (grant No. 082300420110) and the Natural Science Foundation of Henan Province Education Department, China (grant No. 2007150036) for financial support.

References

Hermann, B., Erwin, H. & Hansjorg, K. (2003). US Patent No. 2 003 176 284. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ulrich, H. (2004). US Patent No. 2 004 033 897. Google Scholar