Glutaric acid–2-(pyridin-4-yl)-1H-benzimidazole (1/1)

Lin, S.; Jia, R.; He, A.; Gao, X.

doi:10.1107/S1600536811049695

organic compounds

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Volume 67| Part 12| December 2011| Page o3463

https://doi.org/10.1107/S1600536811049695

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Glutaric acid–2-(pyridin-4-yl)-1H-benzimidazole (1/1)

Songzhu Lin,^a ^* Ruokun Jia,^a Aimin He ^a and Xiaoli Gao ^a

^aNortheast Dianli University, Jilin 132012, People's Republic of China
^*Correspondence e-mail: songzhulin@hotmail.com

(Received 13 October 2011; accepted 21 November 2011; online 30 November 2011)

The crystal structure of the title co-crystal, C₁₂H₉N₃·C₅H₈O₄, N—H⋯O and O—H⋯N hydrogen bonds link the components. There are also π–π stacking interactions between the imidazole rings, between the imidazole and pyridine rings and between the pyridine and benzene rings [centroid–centroid distances = 3.643 (2), 3.573 (2) and 3.740 (1)Å, respectively].

Related literature

For background to hydrogen bonds, see: Moorthy et al. (2002 ); Muthuraman et al. (2000 ); Nangia & Desiraju (1999 ); Bhattacharjya et al. (2004 ). For related structures, see: Bei et al. (2000 ); Ozbey et al. (1998 ).

Experimental

Crystal data

C₁₂H₉N₃·C₅H₈O₄
M_r = 327.34
Triclinic, $[P \overline 1]$
a = 7.4384 (15) Å
b = 8.9911 (18) Å
c = 11.868 (2) Å
α = 86.67 (3)°
β = 81.66 (3)°
γ = 85.57 (3)°
V = 782.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.20 × 0.17 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
6041 measured reflections
2664 independent reflections
1657 reflections with I > 2σ(I)
R_int = 0.024
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.149
S = 1.11
2664 reflections
226 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.10	2.957 (3)	176
O1—H2⋯N3ⁱⁱ	0.87 (1)	1.75 (1)	2.615 (3)	173 (4)
O4—H1⋯N2	1.02 (4)	1.71 (4)	2.686 (3)	158 (3)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, y-1, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ); 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: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811049695/fj2466sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049695/fj2466Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049695/fj2466Isup3.cml

checkCIF report

Comment top

The strong (O—H···O) and weak (C—H···O) hydrogen bonds, the halogen bond (C—X···O) and the weak C—H···π interaction, have been well characterized and exploited in the design of molecular assemblies (Moorthy et al., 2002; Muthuraman et al., 2000; Nangia and Desiraju, 1999; Bhattacharjya et al., 2004). Our interest in benzimidazole stems from their biological activity (Bei et al., 2000; Ozbey et al., 1998). In this paper, we sysnthesized the title compound and report its structure.

Scheme I

The compound consists of 2-(pyridin-4-yl)-1H-benzimidazole and glutaric acid. In the title compound, the dihedral angle between the imidazole and the benzene was 1.40 (2)°, while the benzimidazole and the pyridine was 5.25 (1)°. It results that the all atoms in the 2-(pyridin-4-yl)-1H-benzimidazole are not coplanar strictly. In the part of glutaric acid, four atoms O1, O2, C13, C14 are lying in a same plane (p1) with the maximum diviation of 0.002° for C13, while other four atoms O3, O4, C16, C17 lying in another plane (p2) with the maximum diviation of 0.001% for O3. The dihedral angle between p1 and p2 is 10.50 (2)°.

In the lattice, there exist some kinds of hydrogen bonds. It forms one-dimension stairway structure between 2-(pyridin-4-yl)-1H-benzimidazole and glutaric acid via N—H···O, O—H···N hydrogen bonds (figure 2a and 2 b). Two adjacent strairway chains formed two dimension structure via the C—H···O intermolecular interaction.

In addition, there exists some π–π interactions between the rings [Cg1···Cg1=3.643 (2), Cg1···Cg2= 3.573 (2) and Cg2···Cg3=3.740 (1), respectively (Cg1, Cg2, Cg3 refer to the centroid of imidazole N1, C1, C6, N2, C7; the pyridine N3, C8, C9, C10, C11, C12 and the phenyl ring C1, C2, C3, C4, C5, C6, respectively)]. The π–π interaction, as well as the inter- and intra- hydrogen bond stabilized the crystal structure.

Related literature top

For background to hydrogen bonds, see: Moorthy et al. (2002); Muthuraman et al. (2000); Nangia & Desiraju (1999); Bhattacharjya et al. (2004). For related structures, see: Bei et al. (2000); Ozbey et al. (1998).

Experimental top

The title compound was obtained by 2-Pyridin-4-yl-1H-benzoimidazole (0.020 g, 0.1 mmol) and glutaric acid (0.013 g, 0.1 mmol) dissolved in 30 ml solution mixed with ethanol and water by 2:1(V/V) was heated to refluxed for 6 h and cooled to the room temperature. Single crystals suitable for x-ray measurements were obtained by recrystallization at room temperature.

Structure description top

Scheme I

For background to hydrogen bonds, see: Moorthy et al. (2002); Muthuraman et al. (2000); Nangia & Desiraju (1999); Bhattacharjya et al. (2004). For related structures, see: Bei et al. (2000); Ozbey et al. (1998).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); 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: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. One-dimensional bend structure of the title compound.
	Fig. 3. Two-dimensional structure of the title compound.

Pentane-1,5-dioic acid–2-(pyridin-4-yl)-1H-benzimidazole (1/1) top

Crystal data top

C₁₂H₉N₃·C₅H₈O₄	Z = 2
M_r = 327.34	F(000) = 344
Triclinic, P1	D_x = 1.390 Mg m⁻³
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4384 (15) Å	Cell parameters from 25 reflections
b = 8.9911 (18) Å	θ = 4–14°
c = 11.868 (2) Å	µ = 0.10 mm⁻¹
α = 86.67 (3)°	T = 293 K
β = 81.66 (3)°	Block, colorless
γ = 85.57 (3)°	0.20 × 0.17 × 0.15 mm
V = 782.1 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.024
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 3.1°
Graphite monochromator	h = −7→7
ω scans	k = −10→10
6041 measured reflections	l = −14→13
2664 independent reflections	3 standard reflections every 100 reflections
1657 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0825P)² + 0.020P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
2664 reflections	Δρ_max = 0.35 e Å⁻³
226 parameters	Δρ_min = −0.32 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (5)

Crystal data top

C₁₂H₉N₃·C₅H₈O₄	γ = 85.57 (3)°
M_r = 327.34	V = 782.1 (3) Å³
Triclinic, P1	Z = 2
a = 7.4384 (15) Å	Mo Kα radiation
b = 8.9911 (18) Å	µ = 0.10 mm⁻¹
c = 11.868 (2) Å	T = 293 K
α = 86.67 (3)°	0.20 × 0.17 × 0.15 mm
β = 81.66 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.024
6041 measured reflections	3 standard reflections every 100 reflections
2664 independent reflections	intensity decay: none
1657 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.35 e Å⁻³
2664 reflections	Δρ_min = −0.32 e Å⁻³
226 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	0.2659 (2)	0.5349 (2)	0.58023 (17)	0.0435 (5)
H1A	0.2940	0.6038	0.6206	0.052*
N2	0.2164 (2)	0.4197 (2)	0.42719 (17)	0.0432 (5)
N3	0.4250 (3)	0.9193 (2)	0.24990 (19)	0.0526 (6)
C1	0.1814 (3)	0.3243 (2)	0.5230 (2)	0.0403 (6)
C2	0.1261 (3)	0.1787 (3)	0.5328 (2)	0.0478 (6)
H2B	0.1037	0.1309	0.4693	0.057*
C3	0.1057 (3)	0.1083 (3)	0.6392 (2)	0.0515 (7)
H3B	0.0690	0.0112	0.6477	0.062*
C4	0.1387 (3)	0.1791 (3)	0.7345 (2)	0.0540 (7)
H4A	0.1251	0.1275	0.8051	0.065*
C5	0.1912 (3)	0.3235 (3)	0.7273 (2)	0.0508 (7)
H5A	0.2117	0.3707	0.7915	0.061*
C6	0.2117 (3)	0.3952 (3)	0.6200 (2)	0.0408 (6)
C7	0.2664 (3)	0.5429 (2)	0.4655 (2)	0.0405 (6)
C8	0.3189 (3)	0.6750 (3)	0.3922 (2)	0.0416 (6)
C9	0.3303 (3)	0.6703 (3)	0.2746 (2)	0.0502 (7)
H9A	0.3025	0.5851	0.2416	0.060*
C10	0.3835 (3)	0.7942 (3)	0.2073 (2)	0.0563 (7)
H10A	0.3908	0.7903	0.1286	0.068*
C11	0.4129 (3)	0.9229 (3)	0.3626 (2)	0.0520 (7)
H11A	0.4408	1.0097	0.3934	0.062*
C12	0.3614 (3)	0.8050 (3)	0.4361 (2)	0.0488 (6)
H12A	0.3553	0.8125	0.5144	0.059*
O1	−0.3978 (3)	0.1206 (2)	0.12019 (17)	0.0654 (6)
O2	−0.3751 (2)	0.2383 (2)	0.27704 (16)	0.0599 (5)
O3	0.2390 (4)	0.3965 (3)	0.1101 (2)	0.1041 (9)
O4	0.1264 (3)	0.2629 (2)	0.26029 (18)	0.0776 (7)
C13	−0.3421 (3)	0.2273 (3)	0.1748 (2)	0.0490 (6)
C14	−0.2312 (4)	0.3340 (3)	0.0967 (2)	0.0618 (8)
H14A	−0.1852	0.4040	0.1429	0.074*
H14B	−0.3110	0.3908	0.0497	0.074*
C15	−0.0728 (4)	0.2637 (3)	0.0197 (2)	0.0597 (7)
H15A	−0.0195	0.3404	−0.0327	0.072*
H15B	−0.1176	0.1914	−0.0252	0.072*
C16	0.0758 (4)	0.1854 (3)	0.0833 (2)	0.0619 (8)
H16A	0.0244	0.1063	0.1340	0.074*
H16B	0.1714	0.1405	0.0288	0.074*
C17	0.1557 (4)	0.2930 (3)	0.1513 (3)	0.0601 (8)
H1	0.173 (5)	0.338 (4)	0.308 (3)	0.123 (13)*
H2	−0.456 (4)	0.058 (4)	0.167 (3)	0.133 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0502 (11)	0.0392 (11)	0.0437 (13)	−0.0103 (8)	−0.0095 (9)	−0.0083 (9)
N2	0.0464 (11)	0.0400 (12)	0.0465 (13)	−0.0084 (9)	−0.0127 (9)	−0.0063 (10)
N3	0.0573 (12)	0.0472 (13)	0.0568 (15)	−0.0157 (10)	−0.0133 (10)	−0.0024 (11)
C1	0.0380 (12)	0.0384 (13)	0.0466 (15)	−0.0042 (9)	−0.0102 (10)	−0.0064 (11)
C2	0.0524 (14)	0.0402 (14)	0.0547 (17)	−0.0087 (11)	−0.0144 (11)	−0.0120 (12)
C3	0.0589 (15)	0.0391 (14)	0.0592 (18)	−0.0121 (11)	−0.0122 (12)	−0.0039 (13)
C4	0.0646 (16)	0.0458 (15)	0.0515 (17)	−0.0079 (12)	−0.0054 (13)	−0.0029 (13)
C5	0.0653 (16)	0.0461 (15)	0.0427 (16)	−0.0088 (12)	−0.0079 (12)	−0.0089 (12)
C6	0.0403 (12)	0.0364 (13)	0.0472 (15)	−0.0047 (9)	−0.0075 (10)	−0.0084 (11)
C7	0.0375 (12)	0.0408 (13)	0.0454 (15)	−0.0066 (10)	−0.0098 (10)	−0.0061 (11)
C8	0.0387 (12)	0.0406 (13)	0.0475 (15)	−0.0064 (9)	−0.0089 (10)	−0.0071 (11)
C9	0.0582 (15)	0.0474 (15)	0.0499 (16)	−0.0168 (11)	−0.0160 (12)	−0.0054 (12)
C10	0.0678 (17)	0.0572 (17)	0.0500 (17)	−0.0221 (13)	−0.0207 (13)	0.0012 (13)
C11	0.0566 (15)	0.0448 (15)	0.0569 (18)	−0.0151 (11)	−0.0064 (12)	−0.0102 (13)
C12	0.0523 (14)	0.0485 (15)	0.0470 (16)	−0.0128 (11)	−0.0049 (11)	−0.0082 (12)
O1	0.0996 (15)	0.0540 (12)	0.0469 (12)	−0.0322 (11)	−0.0076 (10)	−0.0088 (10)
O2	0.0784 (12)	0.0601 (12)	0.0441 (12)	−0.0230 (9)	−0.0063 (9)	−0.0081 (9)
O3	0.170 (2)	0.0867 (17)	0.0689 (16)	−0.0736 (17)	−0.0346 (15)	0.0149 (13)
O4	0.1193 (18)	0.0732 (15)	0.0487 (14)	−0.0464 (13)	−0.0185 (12)	−0.0038 (11)
C13	0.0623 (15)	0.0415 (14)	0.0453 (17)	−0.0102 (11)	−0.0097 (12)	−0.0044 (12)
C14	0.090 (2)	0.0469 (16)	0.0497 (17)	−0.0231 (14)	−0.0054 (15)	−0.0005 (13)
C15	0.0806 (18)	0.0623 (18)	0.0390 (16)	−0.0253 (14)	−0.0061 (13)	−0.0068 (13)
C16	0.088 (2)	0.0522 (17)	0.0492 (18)	−0.0181 (14)	−0.0124 (14)	−0.0107 (14)
C17	0.0833 (19)	0.0498 (17)	0.0520 (19)	−0.0205 (14)	−0.0195 (14)	0.0043 (14)

Geometric parameters (Å, º) top

N1—C7	1.359 (3)	C9—H9A	0.9300
N1—C6	1.385 (3)	C10—H10A	0.9300
N1—H1A	0.8600	C11—C12	1.375 (3)
N2—C7	1.320 (3)	C11—H11A	0.9300
N2—C1	1.390 (3)	C12—H12A	0.9300
N3—C11	1.330 (3)	O1—C13	1.313 (3)
N3—C10	1.334 (3)	O1—H2	0.866 (10)
C1—C2	1.396 (3)	O2—C13	1.211 (3)
C1—C6	1.402 (3)	O3—C17	1.199 (3)
C2—C3	1.373 (3)	O4—C17	1.296 (3)
C2—H2B	0.9300	O4—H1	1.02 (4)
C3—C4	1.390 (4)	C13—C14	1.503 (3)
C3—H3B	0.9300	C14—C15	1.504 (4)
C4—C5	1.379 (4)	C14—H14A	0.9700
C4—H4A	0.9300	C14—H14B	0.9700
C5—C6	1.387 (4)	C15—C16	1.532 (4)
C5—H5A	0.9300	C15—H15A	0.9700
C7—C8	1.475 (3)	C15—H15B	0.9700
C8—C12	1.383 (3)	C16—C17	1.503 (4)
C8—C9	1.389 (4)	C16—H16A	0.9700
C9—C10	1.381 (3)	C16—H16B	0.9700

C7—N1—C6	107.18 (19)	C9—C10—H10A	118.5
C7—N1—H1A	126.4	N3—C11—C12	123.4 (2)
C6—N1—H1A	126.4	N3—C11—H11A	118.3
C7—N2—C1	105.23 (19)	C12—C11—H11A	118.3
C11—N3—C10	117.5 (2)	C11—C12—C8	119.2 (2)
N2—C1—C2	130.2 (2)	C11—C12—H12A	120.4
N2—C1—C6	109.62 (19)	C8—C12—H12A	120.4
C2—C1—C6	120.2 (2)	C13—O1—H2	111 (3)
C3—C2—C1	117.8 (2)	C17—O4—H1	114 (2)
C3—C2—H2B	121.1	O2—C13—O1	123.9 (2)
C1—C2—H2B	121.1	O2—C13—C14	123.5 (2)
C2—C3—C4	121.4 (2)	O1—C13—C14	112.6 (2)
C2—C3—H3B	119.3	C13—C14—C15	115.5 (2)
C4—C3—H3B	119.3	C13—C14—H14A	108.4
C5—C4—C3	121.9 (2)	C15—C14—H14A	108.4
C5—C4—H4A	119.0	C13—C14—H14B	108.4
C3—C4—H4A	119.0	C15—C14—H14B	108.4
C4—C5—C6	116.9 (2)	H14A—C14—H14B	107.5
C4—C5—H5A	121.6	C14—C15—C16	113.8 (2)
C6—C5—H5A	121.6	C14—C15—H15A	108.8
N1—C6—C5	133.1 (2)	C16—C15—H15A	108.8
N1—C6—C1	105.2 (2)	C14—C15—H15B	108.8
C5—C6—C1	121.7 (2)	C16—C15—H15B	108.8
N2—C7—N1	112.81 (19)	H15A—C15—H15B	107.7
N2—C7—C8	124.0 (2)	C17—C16—C15	111.4 (2)
N1—C7—C8	123.2 (2)	C17—C16—H16A	109.3
C12—C8—C9	117.8 (2)	C15—C16—H16A	109.3
C12—C8—C7	122.3 (2)	C17—C16—H16B	109.3
C9—C8—C7	119.9 (2)	C15—C16—H16B	109.3
C10—C9—C8	118.9 (2)	H16A—C16—H16B	108.0
C10—C9—H9A	120.5	O3—C17—O4	122.6 (3)
C8—C9—H9A	120.5	O3—C17—C16	124.1 (3)
N3—C10—C9	123.1 (3)	O4—C17—C16	113.3 (2)
N3—C10—H10A	118.5

C7—N2—C1—C2	−179.2 (2)	N2—C7—C8—C12	176.6 (2)
C7—N2—C1—C6	0.2 (2)	N1—C7—C8—C12	−4.0 (3)
N2—C1—C2—C3	178.4 (2)	N2—C7—C8—C9	−4.7 (3)
C6—C1—C2—C3	−1.0 (3)	N1—C7—C8—C9	174.8 (2)
C1—C2—C3—C4	0.0 (4)	C12—C8—C9—C10	0.2 (4)
C2—C3—C4—C5	0.8 (4)	C7—C8—C9—C10	−178.6 (2)
C3—C4—C5—C6	−0.7 (4)	C11—N3—C10—C9	−0.3 (4)
C7—N1—C6—C5	178.0 (2)	C8—C9—C10—N3	0.0 (4)
C7—N1—C6—C1	0.0 (2)	C10—N3—C11—C12	0.4 (4)
C4—C5—C6—N1	−178.0 (2)	N3—C11—C12—C8	−0.2 (4)
C4—C5—C6—C1	−0.2 (3)	C9—C8—C12—C11	−0.1 (3)
N2—C1—C6—N1	−0.1 (2)	C7—C8—C12—C11	178.7 (2)
C2—C1—C6—N1	179.4 (2)	O2—C13—C14—C15	126.6 (3)
N2—C1—C6—C5	−178.4 (2)	O1—C13—C14—C15	−52.9 (3)
C2—C1—C6—C5	1.1 (3)	C13—C14—C15—C16	−64.9 (3)
C1—N2—C7—N1	−0.2 (2)	C14—C15—C16—C17	−60.6 (3)
C1—N2—C7—C8	179.28 (19)	C15—C16—C17—O3	−64.2 (4)
C6—N1—C7—N2	0.2 (2)	C15—C16—C17—O4	116.1 (3)
C6—N1—C7—C8	−179.33 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.10	2.957 (3)	176
O1—H2···N3ⁱⁱ	0.87 (1)	1.75 (1)	2.615 (3)	173 (4)
O4—H1···N2	1.02 (4)	1.71 (4)	2.686 (3)	158 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₃·C₅H₈O₄
M_r	327.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4384 (15), 8.9911 (18), 11.868 (2)
α, β, γ (°)	86.67 (3), 81.66 (3), 85.57 (3)
V (Å³)	782.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.17 × 0.15

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6041, 2664, 1657
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.149, 1.11
No. of reflections	2664
No. of parameters	226
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.32

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.10	2.957 (3)	176.3
O1—H2···N3ⁱⁱ	0.866 (10)	1.752 (12)	2.615 (3)	173 (4)
O4—H1···N2	1.02 (4)	1.71 (4)	2.686 (3)	158 (3)

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

Acknowledgements

The authors would like to thank the National Natural Science Foundation of China (51003010) and the Natural Science Foundation of Jilin Province (201115178).

References

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