2,4,5-Tris(pyridin-4-yl)-1H-imidazole monohydrate

Wang, S.-T.; Che, G.-B.; Liu, C.-B.; Wang, X.; Liu, L.

doi:10.1107/S1600536811053013

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o130

doi:10.1107/S1600536811053013

Open

access

2,4,5-Tris(pyridin-4-yl)-1H-imidazole monohydrate

Shen-Tang Wang,^a Guang-Bo Che,^a Chun-Bo Liu,^a ^* Xing Wang ^a and Ling Liu ^a

^aSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, People's Republic of China
^*Correspondence e-mail: guangbocheujs@yahoo.com.cn

(Received 4 November 2011; accepted 9 December 2011; online 14 December 2011)

In the crystal structure of the title compound, C₁₈H₁₃N₅·H₂O, adjacent molecules are linked by O—H⋯N and N—H⋯O hydrogen bonds, generating a chain propagating along [001].

Related literature

For the use of 2,4,5-tri(4-pyridyl)imidazole in the construction of metal-organic coordination polymers, see: Wang et al. (2009 ); Liang et al. (2009 ). For related structures, see: Jiang & Hou (2011 ); Li (2011 ); Li & Xia (2011 ). For the preparation, see: Proskurnina et al. (2002 ).

Experimental

Crystal data

C₁₈H₁₃N₅·H₂O
M_r = 317.35
Triclinic, $[P \overline 1]$
a = 8.1510 (16) Å
b = 9.5210 (19) Å
c = 11.506 (2) Å
α = 103.80 (3)°
β = 105.64 (3)°
γ = 101.03 (3)°
V = 803.3 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.2 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.970, T_max = 1.000
7510 measured reflections
2912 independent reflections
1792 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.125
S = 1.02
2876 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N5ⁱ	0.85	1.99	2.843 (3)	177
N1—H1⋯O1	0.89	1.85	2.741 (3)	176
O1—H1B⋯N4ⁱⁱ	0.85	1.94	2.787 (3)	172
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x, y, z+1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811053013/zj2036sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053013/zj2036Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053013/zj2036Isup3.cml

checkCIF report

Comment top

In the 2,4,5-tri(4-pyridyl)imidazole three pyridyl groups (pyridyl ring B (C4-C8 and N3), C (C9-C13 and N4), D (C14-C18 and N5)) are directly connected with the imidazole ring A (C1-C3 , N1 and N2). The dihedral angles between the mean planes of pyridyl ring B and imidazole ring A, pyridyl ring C and imidazole ring A, and pyridyl ring D and imidazole ring A are 9.1 (7) °, 21.5 (5) °, 45.5 (1) °, respectively.

We report herein on the crystal structure of the title compound (Fig. 1). In the crystal lattice the molecules are linked by O—H···N and N—H···O hydrogen bonds (Jiang et al. 2011; Li et al. 2011; Li 2011) interactions to generate a one-dimensional double chain structure (Fig. 2).

Related literature top

For the use of 2,4,5-tri(4-pyridyl)imidazole in the construction of metal-organic coordination polymers, see: Wang et al. (2009); Liang et al. (2009). For related structures, see: Jiang & Hou (2011); Li (2011); Li & Xia (2011). For the preparation, see: Proskurnina et al. (2002).

Experimental top

The 2,4,5-tri(4-pyridyl)imidazole was prepared by the methord reported in the literature (Proskurnina et al. 2002). A mixture of 2,4,5-tri(4-pyridyl)imidazole (0.030 g, 0.1 mmol), 2 drops of 1 mol/L HCl and water (10 mL) was placed in a 25 mL Teflon-lined autoclave and heated for 3 d at 433 K under autogenous pressure. Upon cooling and opening the bomb, colourless block-shaped crystals were obtained, then washed with water and dried in air.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. All H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The one-dimensional superamolecular structure linked by the hydrogen bonds.

2,4,5-Tris(pyridin-4-yl)-1H-imidazole monohydrate top

Crystal data top

C₁₈H₁₃N₅·H₂O	Z = 2
M_r = 317.35	F(000) = 332
Triclinic, P1	D_x = 1.312 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1510 (16) Å	Cell parameters from 3107 reflections
b = 9.5210 (19) Å	θ = 3.0–25.2°
c = 11.506 (2) Å	µ = 0.09 mm⁻¹
α = 103.80 (3)°	T = 293 K
β = 105.64 (3)°	Prism, colourless
γ = 101.03 (3)°	0.35 × 0.25 × 0.2 mm
V = 803.3 (4) Å³

Data collection top

Bruker SMART diffractometer	2912 independent reflections
Radiation source: fine-focus sealed tube	1792 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 25.2°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
T_min = 0.970, T_max = 1.000	k = −11→11
7510 measured reflections	l = −13→13

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0171P)² + 0.605P] where P = (F_o² + 2F_c²)/3
2876 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₃N₅·H₂O	γ = 101.03 (3)°
M_r = 317.35	V = 803.3 (4) Å³
Triclinic, P1	Z = 2
a = 8.1510 (16) Å	Mo Kα radiation
b = 9.5210 (19) Å	µ = 0.09 mm⁻¹
c = 11.506 (2) Å	T = 293 K
α = 103.80 (3)°	0.35 × 0.25 × 0.2 mm
β = 105.64 (3)°

Data collection top

Bruker SMART diffractometer	2912 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1792 reflections with I > 2σ(I)
T_min = 0.970, T_max = 1.000	R_int = 0.040
7510 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
2876 reflections	Δρ_min = −0.17 e Å⁻³
218 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
N1	0.2548 (3)	0.5006 (2)	0.26415 (19)	0.0544 (6)
H1	0.2800	0.5437	0.3469	0.082*
N2	0.1414 (3)	0.3416 (2)	0.06806 (19)	0.0542 (6)
N3	−0.0531 (4)	0.0012 (3)	0.3185 (2)	0.0738 (7)
N4	0.2559 (4)	0.5283 (3)	−0.2901 (2)	0.0749 (7)
N5	0.5288 (4)	1.0560 (3)	0.3379 (3)	0.0764 (8)
C1	0.1603 (3)	0.3582 (3)	0.1895 (2)	0.0518 (6)
C2	0.2265 (3)	0.4798 (3)	0.0649 (2)	0.0523 (6)
C3	0.2960 (3)	0.5811 (3)	0.1858 (2)	0.0530 (7)
C4	0.0870 (3)	0.2404 (3)	0.2365 (2)	0.0520 (6)
C5	0.1271 (4)	0.2521 (3)	0.3637 (3)	0.0671 (8)
H5A	0.2026	0.3399	0.4252	0.080*
C6	0.0536 (4)	0.1317 (3)	0.3987 (3)	0.0739 (9)
H6A	0.0812	0.1433	0.4849	0.089*
C7	−0.0932 (4)	−0.0074 (3)	0.1966 (3)	0.0754 (9)
H7A	−0.1703	−0.0962	0.1374	0.091*
C8	−0.0284 (4)	0.1062 (3)	0.1517 (3)	0.0668 (8)
H8A	−0.0621	0.0926	0.0650	0.080*
C9	0.2386 (3)	0.4986 (3)	−0.0558 (2)	0.0527 (6)
C10	0.1214 (4)	0.4006 (3)	−0.1700 (2)	0.0594 (7)
H10A	0.0342	0.3211	−0.1709	0.071*
C11	0.1334 (4)	0.4203 (3)	−0.2821 (3)	0.0708 (8)
H11A	0.0505	0.3537	−0.3572	0.085*
C12	0.3716 (4)	0.6201 (4)	−0.1801 (3)	0.0775 (9)
H12A	0.4600	0.6962	−0.1826	0.093*
C13	0.3698 (4)	0.6105 (3)	−0.0626 (3)	0.0681 (8)
H13A	0.4552	0.6778	0.0110	0.082*
C14	0.3805 (4)	0.7431 (3)	0.2368 (2)	0.0549 (7)
C15	0.3141 (4)	0.8416 (3)	0.1767 (3)	0.0675 (8)
H15A	0.2185	0.8049	0.1015	0.081*
C16	0.3925 (4)	0.9939 (3)	0.2305 (3)	0.0754 (9)
H16A	0.3470	1.0577	0.1890	0.090*
C17	0.5915 (4)	0.9608 (3)	0.3939 (3)	0.0735 (9)
H17A	0.6879	1.0009	0.4685	0.088*
C18	0.5219 (4)	0.8055 (3)	0.3480 (3)	0.0650 (8)
H18A	0.5701	0.7446	0.3918	0.078*
O1	0.3155 (4)	0.6367 (2)	0.51602 (18)	0.1058 (10)
H1A	0.3597	0.7298	0.5581	0.159*
H1B	0.3044	0.5992	0.5745	0.159*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0703 (14)	0.0475 (12)	0.0430 (12)	0.0090 (10)	0.0198 (10)	0.0139 (9)
N2	0.0711 (15)	0.0475 (12)	0.0439 (12)	0.0088 (10)	0.0215 (11)	0.0167 (9)
N3	0.0983 (19)	0.0555 (14)	0.0683 (17)	0.0082 (13)	0.0323 (15)	0.0249 (13)
N4	0.102 (2)	0.0736 (16)	0.0558 (15)	0.0144 (15)	0.0375 (15)	0.0265 (13)
N5	0.0884 (19)	0.0549 (15)	0.0791 (18)	0.0055 (14)	0.0317 (16)	0.0152 (14)
C1	0.0689 (17)	0.0422 (13)	0.0430 (14)	0.0118 (12)	0.0187 (13)	0.0129 (11)
C2	0.0652 (16)	0.0482 (14)	0.0426 (14)	0.0091 (12)	0.0199 (12)	0.0153 (11)
C3	0.0660 (17)	0.0482 (14)	0.0446 (14)	0.0091 (12)	0.0201 (13)	0.0171 (11)
C4	0.0680 (17)	0.0428 (13)	0.0470 (15)	0.0122 (12)	0.0209 (13)	0.0174 (11)
C5	0.097 (2)	0.0510 (15)	0.0484 (16)	0.0064 (15)	0.0245 (15)	0.0162 (13)
C6	0.111 (3)	0.0599 (18)	0.0564 (18)	0.0163 (17)	0.0360 (18)	0.0236 (15)
C7	0.094 (2)	0.0519 (17)	0.068 (2)	−0.0007 (15)	0.0184 (17)	0.0212 (15)
C8	0.088 (2)	0.0522 (16)	0.0527 (16)	0.0074 (15)	0.0191 (15)	0.0174 (13)
C9	0.0659 (17)	0.0511 (14)	0.0462 (14)	0.0145 (12)	0.0225 (13)	0.0204 (12)
C10	0.0738 (18)	0.0566 (16)	0.0473 (15)	0.0113 (14)	0.0228 (14)	0.0169 (13)
C11	0.090 (2)	0.0732 (19)	0.0474 (17)	0.0160 (17)	0.0259 (16)	0.0173 (14)
C12	0.097 (2)	0.071 (2)	0.068 (2)	0.0054 (17)	0.0402 (19)	0.0273 (17)
C13	0.079 (2)	0.0656 (18)	0.0517 (17)	0.0000 (15)	0.0251 (15)	0.0158 (14)
C14	0.0670 (17)	0.0486 (14)	0.0492 (15)	0.0082 (12)	0.0251 (13)	0.0148 (12)
C15	0.078 (2)	0.0519 (16)	0.0657 (19)	0.0083 (14)	0.0172 (16)	0.0212 (14)
C16	0.087 (2)	0.0536 (17)	0.086 (2)	0.0151 (16)	0.0285 (19)	0.0265 (16)
C17	0.080 (2)	0.0604 (18)	0.0624 (19)	−0.0019 (16)	0.0216 (16)	0.0061 (15)
C18	0.077 (2)	0.0548 (16)	0.0552 (17)	0.0068 (14)	0.0185 (15)	0.0156 (13)
O1	0.187 (3)	0.0597 (13)	0.0500 (12)	−0.0125 (14)	0.0451 (14)	0.0087 (10)

Geometric parameters (Å, º) top

N1—C1	1.363 (3)	C7—H7A	0.9300
N1—C3	1.381 (3)	C8—H8A	0.9300
N1—H1	0.8907	C9—C10	1.381 (3)
N2—C1	1.331 (3)	C9—C13	1.390 (3)
N2—C2	1.379 (3)	C10—C11	1.373 (4)
N3—C6	1.326 (4)	C10—H10A	0.9300
N3—C7	1.329 (4)	C11—H11A	0.9300
N4—C11	1.329 (4)	C12—C13	1.381 (4)
N4—C12	1.330 (4)	C12—H12A	0.9300
N5—C16	1.330 (4)	C13—H13A	0.9300
N5—C17	1.333 (4)	C14—C18	1.378 (4)
C1—C4	1.454 (3)	C14—C15	1.397 (4)
C2—C3	1.383 (3)	C15—C16	1.378 (4)
C2—C9	1.469 (3)	C15—H15A	0.9300
C3—C14	1.463 (3)	C16—H16A	0.9300
C4—C5	1.383 (3)	C17—C18	1.390 (4)
C4—C8	1.385 (3)	C17—H17A	0.9300
C5—C6	1.387 (4)	C18—H18A	0.9300
C5—H5A	0.9300	O1—H1A	0.8543
C6—H6A	0.9300	O1—H1B	0.8500
C7—C8	1.382 (4)

C1—N1—C3	107.5 (2)	C10—C9—C13	116.4 (2)
C1—N1—H1	130.1	C10—C9—C2	120.8 (2)
C3—N1—H1	122.1	C13—C9—C2	122.8 (2)
C1—N2—C2	105.6 (2)	C11—C10—C9	120.2 (3)
C6—N3—C7	115.0 (2)	C11—C10—H10A	119.9
C11—N4—C12	115.6 (2)	C9—C10—H10A	119.9
C16—N5—C17	116.0 (3)	N4—C11—C10	124.1 (3)
N2—C1—N1	111.3 (2)	N4—C11—H11A	117.9
N2—C1—C4	124.4 (2)	C10—C11—H11A	117.9
N1—C1—C4	124.3 (2)	N4—C12—C13	124.6 (3)
N2—C2—C3	110.2 (2)	N4—C12—H12A	117.7
N2—C2—C9	119.8 (2)	C13—C12—H12A	117.7
C3—C2—C9	130.0 (2)	C12—C13—C9	119.1 (3)
N1—C3—C2	105.3 (2)	C12—C13—H13A	120.5
N1—C3—C14	120.4 (2)	C9—C13—H13A	120.5
C2—C3—C14	134.0 (2)	C18—C14—C15	117.3 (2)
C5—C4—C8	116.3 (2)	C18—C14—C3	122.0 (2)
C5—C4—C1	123.8 (2)	C15—C14—C3	120.6 (2)
C8—C4—C1	119.9 (2)	C16—C15—C14	118.9 (3)
C4—C5—C6	119.4 (3)	C16—C15—H15A	120.5
C4—C5—H5A	120.3	C14—C15—H15A	120.5
C6—C5—H5A	120.3	N5—C16—C15	124.5 (3)
N3—C6—C5	124.9 (3)	N5—C16—H16A	117.7
N3—C6—H6A	117.5	C15—C16—H16A	117.7
C5—C6—H6A	117.5	N5—C17—C18	124.1 (3)
N3—C7—C8	124.6 (3)	N5—C17—H17A	117.9
N3—C7—H7A	117.7	C18—C17—H17A	117.9
C8—C7—H7A	117.7	C14—C18—C17	119.1 (3)
C7—C8—C4	119.7 (3)	C14—C18—H18A	120.4
C7—C8—H8A	120.1	C17—C18—H18A	120.4
C4—C8—H8A	120.1	H1A—O1—H1B	100.9

C2—N2—C1—N1	−0.5 (3)	N2—C2—C9—C10	21.5 (4)
C2—N2—C1—C4	178.6 (3)	C3—C2—C9—C10	−161.6 (3)
C3—N1—C1—N2	1.3 (3)	N2—C2—C9—C13	−156.1 (3)
C3—N1—C1—C4	−177.8 (3)	C3—C2—C9—C13	20.8 (5)
C1—N2—C2—C3	−0.5 (3)	C13—C9—C10—C11	−2.7 (4)
C1—N2—C2—C9	176.9 (2)	C2—C9—C10—C11	179.5 (3)
C1—N1—C3—C2	−1.6 (3)	C12—N4—C11—C10	0.2 (5)
C1—N1—C3—C14	173.1 (2)	C9—C10—C11—N4	1.6 (5)
N2—C2—C3—N1	1.3 (3)	C11—N4—C12—C13	−0.8 (5)
C9—C2—C3—N1	−175.8 (3)	N4—C12—C13—C9	−0.5 (5)
N2—C2—C3—C14	−172.3 (3)	C10—C9—C13—C12	2.2 (4)
C9—C2—C3—C14	10.6 (5)	C2—C9—C13—C12	179.9 (3)
N2—C1—C4—C5	170.9 (3)	N1—C3—C14—C18	45.8 (4)
N1—C1—C4—C5	−10.2 (4)	C2—C3—C14—C18	−141.4 (3)
N2—C1—C4—C8	−8.3 (4)	N1—C3—C14—C15	−131.1 (3)
N1—C1—C4—C8	170.7 (3)	C2—C3—C14—C15	41.7 (5)
C8—C4—C5—C6	0.8 (4)	C18—C14—C15—C16	0.2 (4)
C1—C4—C5—C6	−178.4 (3)	C3—C14—C15—C16	177.3 (3)
C7—N3—C6—C5	−2.3 (5)	C17—N5—C16—C15	0.7 (5)
C4—C5—C6—N3	1.1 (5)	C14—C15—C16—N5	−0.3 (5)
C6—N3—C7—C8	1.7 (5)	C16—N5—C17—C18	−0.9 (5)
N3—C7—C8—C4	0.1 (5)	C15—C14—C18—C17	−0.4 (4)
C5—C4—C8—C7	−1.3 (4)	C3—C14—C18—C17	−177.4 (3)
C1—C4—C8—C7	177.9 (3)	N5—C17—C18—C14	0.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N5ⁱ	0.85	1.99	2.843 (3)	177
N1—H1···O1	0.89	1.85	2.741 (3)	176
O1—H1B···N4ⁱⁱ	0.85	1.94	2.787 (3)	172

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃N₅·H₂O
M_r	317.35
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.1510 (16), 9.5210 (19), 11.506 (2)
α, β, γ (°)	103.80 (3), 105.64 (3), 101.03 (3)
V (Å³)	803.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.25 × 0.2

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.970, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7510, 2912, 1792
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.125, 1.02
No. of reflections	2876
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N5ⁱ	0.85	1.99	2.843 (3)	177.3
N1—H1···O1	0.89	1.85	2.741 (3)	175.5
O1—H1B···N4ⁱⁱ	0.85	1.94	2.787 (3)	172.4

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

Acknowledgements

The authors thank Jiangsu University for supporting this work.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jiang, Y.-K. & Hou, G.-G. (2011). Acta Cryst. E67, o3073. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, H.-D. (2011). Acta Cryst. E67, o3156. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, C.-R. & Xia, Z.-Q. (2011). Acta Cryst. E67, o2481. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liang, X.-Q., Zhou, X.-H., Chen, C., Xiao, H.-P., Li, Y.-Z., Zuo, J.-L. & You, X.-Z. (2009). Cryst. Growth Des. 9, 1041–1053. Web of Science CSD CrossRef CAS Google Scholar
Proskurnina, M. V., Lozinskaya, N. A., Tkachenko, S. E. & Zefirov, N. S. (2002). Russ. J. Org. Chem. 38, 1149–1153. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, L., Gu, W., Deng, J.-X., Liu, M.-L., Xu, N. & Liu, X. (2009). Z. Anorg. Allg. Chem, 635, 1124–1128. Web of Science CSD CrossRef Google Scholar