Bis[3,3′-(piperazine-1,4-di­yl)­dipropan­aminium] di-μ2-sulfido-bis­[disulfido­german­ate(IV)]

Wang, N.-N.; Xu, C.; Duan, T.; Chen, Q.; Zhang, Q.-F.

doi:10.1107/S1600536812030334

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page m1046

https://doi.org/10.1107/S1600536812030334

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Bis[3,3′-(piperazine-1,4-diyl)dipropanaminium] di-μ₂-sulfido-bis[disulfidogermanate(IV)]

Nian-Nian Wang,^a Chao Xu,^a Taike Duan,^a Qun Chen ^b and Qian-Feng Zhang ^a,^b ^*

^aInstitute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma'anshan, Anhui 243002, People's Republic of China, and ^bDepartment of Applied Chemistry, School of Petrochemical Engineering, Changzhou University, Jiangsu 213164, People's Republic of China
^*Correspondence e-mail: zhangqf@ahut.edu.cn

(Received 5 May 2012; accepted 3 July 2012; online 10 July 2012)

In the title compound, (C₁₀H₂₆N₄)₂[Ge₂S₆], the dimeric [Ge₂S₆]⁴⁻ anion formed by two edge-sharing GeS₄ tetrahedral units lies around an inversion centre. The average terminal and bridging Ge—S bond lengths are 2.162 (7) and 2.267 (15) Å, respectively. The inorganic anions and organic cations are organized into a three-dimensional network by numerous N—H⋯S hydrogen bonds.

Related literature

For background to main group metal–chalcogenide compounds, see: Bedard et al. (1999 ); Nellis et al. (1995 ); Blachnik & Fehlker (2001 ); Zheng et al. (2002 , 2005 ). For related structures, see: Jia et al. (2005 ); Xu et al. (2012 ).

Experimental

Crystal data

(C₁₀H₂₆N₄)₂[Ge₂S₆]
M_r = 742.24
Monoclinic, P 2₁ /c
a = 12.0111 (4) Å
b = 7.7759 (3) Å
c = 18.9777 (7) Å
β = 103.569 (1)°
V = 1722.99 (11) Å³
Z = 2
Mo Kα radiation
μ = 2.13 mm⁻¹
T = 296 K
0.38 × 0.29 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.498, T_max = 0.727
16480 measured reflections
3950 independent reflections
3194 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.113
S = 1.07
3950 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 1.15 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯S2ⁱ	0.89	2.48	3.278 (3)	149
N3—H3C⋯S3	0.89	2.34	3.225 (3)	170
N3—H3A⋯S2ⁱⁱ	0.89	2.61	3.440 (3)	157
N3—H3A⋯S3ⁱⁱ	0.89	2.83	3.366 (3)	120
N4—H4C⋯S2ⁱⁱⁱ	0.89	2.53	3.408 (4)	169
N4—H4B⋯S2^iv	0.89	2.34	3.228 (4)	178
N4—H4A⋯S3^v	0.89	2.39	3.275 (4)	173
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) -x, -y, -z; (v) x-1, y-1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812030334/gk2485sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030334/gk2485Isup2.hkl

checkCIF report

Comment top

Since Bedard reported the first porous metal chalcogenide open framework in 1999 (Bedard et al., 1999), a series of binary and ternary metal chalcogenide open-frameworks have been synthesized (Nellis et al., 1995; Zheng et al., 2005). Among the various synthetic methods, hydrothermal technique is the best choice for preparing related compounds due to gentle reaction conditions. Moreover, organic amines are often used as templates in the hydrothermal reactions. Therefore, amines with different structures play an important role for templating effect in the construction of open-frameworks (Zheng et al., 2002). In this paper, we report the hydrothermal synthesis and crystal structure of an amine-templated thiogermanate, [bappH₂]₂[Ge₂S₆] (bapp = 1,4-bis(3-aminopropyl)piperazine).

The title compound crystallizes in the monoclinic space group P2₁/c with a dimeric anion of [Ge₂S₆]^4-located around inversion centre and with diprotonated 1,4-bis(3-aminopropyl)- piperazine in general position (Fig. 1). The dimeric [Ge₂S₆]^4- anion is constructed by two edge-sharing tetrahedral GeS₄ units forming a planar Ge₂S₂ quadrilateral with the four terminal sulfur atoms lying on a perpendicular plane. The S—Ge—S angles in tetrahedral GeS₄ unit are in the ranges from 93.82 (3) to 114.12 (4)°. The average bond length of Ge—S_t (terminal bond) of 2.162 (7) Å is obviously shorter than that of Ge—S_b (bridging bond) [2.267 (15) Å]. The bond length values are similar to those found in the other thiogermanates (Jia et al. 2005; Xu et al., 2012). The two terminal amine groups of 4-bis(3-aminopropyl)piperazine are protonated to balance negative charges of the dimeric anion. The [Ge₂S₆]^4- anions and [bappH₂]²⁺ cations are organized into an extended three-dimensional network by N—H···S hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For background to main group metal–chalcogenide compounds, see: Bedard et al. (1999); Nellis et al. (1995); Blachnik & Fehlker (2001); Zheng et al. (2002, 2005). For related structures, see: Jia et al. (2005); Xu et al. (2012).

Experimental top

GeO₂ (104.6 mg, 1.0 mmol) and S powder (128.0 mg, 4.0 mmol) in the distilled water (4.8550 g) were mixed with 1,4-bis(3-aminopropyl)piperazine (2.5640 g) in a 23 mL Teflon-lined stainless steel autoclave to and stirred for 20 min. The vessel was sealed and heated to 190°C for 6 d and then cooled to room temperature. Colorless flake crystals were obtained and air dried. The yield based on GeO₂ is about 45%. Analysis, calculated for C₂₀H₅₂N₈S₆Ge₂: C 32.4, H 7.06, N 15.1%; found C 32.2, H 6.98, N 14.8 %.

Structure description top

For background to main group metal–chalcogenide compounds, see: Bedard et al. (1999); Nellis et al. (1995); Blachnik & Fehlker (2001); Zheng et al. (2002, 2005). For related structures, see: Jia et al. (2005); Xu et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 structure of the title compound, showing displacement ellipsoids at the 50% probability level. Atoms with the A label were generated by the symmetry operation -x+1, -y+1, -z.
	Fig. 2. Packing diagram of the title compound. Dashed lines donote hydrogen bonds.

Bis[3,3'-(piperazine-1,4-diyl)dipropanaminium] di-µ₂-sulfido-bis[disulfidogermanate(IV)] top

Crystal data top

(C₁₀H₂₆N₄)₂[Ge₂S₆]	F(000) = 776
M_r = 742.24	D_x = 1.431 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6783 reflections
a = 12.0111 (4) Å	θ = 2.5–27.0°
b = 7.7759 (3) Å	µ = 2.13 mm⁻¹
c = 18.9777 (7) Å	T = 296 K
β = 103.569 (1)°	Block, colourless
V = 1722.99 (11) Å³	0.38 × 0.29 × 0.16 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	3950 independent reflections
Radiation source: fine-focus sealed tube	3194 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −15→15
T_min = 0.498, T_max = 0.727	k = −10→6
16480 measured reflections	l = −22→24

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0586P)² + 1.3201P] where P = (F_o² + 2F_c²)/3
3950 reflections	(Δ/σ)_max = 0.001
165 parameters	Δρ_max = 1.15 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

(C₁₀H₂₆N₄)₂[Ge₂S₆]	V = 1722.99 (11) Å³
M_r = 742.24	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0111 (4) Å	µ = 2.13 mm⁻¹
b = 7.7759 (3) Å	T = 296 K
c = 18.9777 (7) Å	0.38 × 0.29 × 0.16 mm
β = 103.569 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3950 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	3194 reflections with I > 2σ(I)
T_min = 0.498, T_max = 0.727	R_int = 0.021
16480 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.07	Δρ_max = 1.15 e Å⁻³
3950 reflections	Δρ_min = −0.36 e Å⁻³
165 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
Ge1	0.53261 (3)	0.44178 (4)	0.080248 (14)	0.04128 (12)
S1	0.38171 (8)	0.59109 (12)	0.01275 (4)	0.0541 (2)
S2	0.47606 (9)	0.19876 (11)	0.11556 (4)	0.0606 (3)
S3	0.63552 (8)	0.59389 (11)	0.16645 (4)	0.0565 (2)
N1	0.1088 (3)	0.4905 (5)	0.1532 (2)	0.0769 (10)
N2	−0.0300 (3)	0.1852 (5)	0.1210 (3)	0.1023 (15)
N3	0.4526 (3)	0.8528 (4)	0.20970 (15)	0.0630 (8)
H3A	0.4580	0.8401	0.2570	0.094*
H3B	0.4769	0.9572	0.2013	0.094*
H3C	0.4956	0.7738	0.1948	0.094*
N4	−0.3627 (4)	−0.0949 (5)	0.0505 (2)	0.0782 (10)
H4A	−0.3673	−0.1851	0.0785	0.117*
H4B	−0.3923	−0.1222	0.0043	0.117*
H4C	−0.4016	−0.0072	0.0630	0.117*
C6	0.1475 (5)	0.3408 (7)	0.1201 (5)	0.121 (2)
H6A	0.2301	0.3319	0.1362	0.145*
H6B	0.1284	0.3547	0.0679	0.145*
C7	0.0954 (5)	0.1827 (7)	0.1388 (5)	0.146 (3)
H7A	0.1227	0.1621	0.1903	0.175*
H7B	0.1207	0.0875	0.1134	0.175*
C8	−0.0710 (4)	0.3401 (7)	0.1474 (4)	0.0981 (16)
H8A	−0.0559	0.3348	0.1999	0.118*
H8B	−0.1532	0.3475	0.1288	0.118*
C9	−0.0168 (4)	0.4974 (6)	0.1262 (4)	0.0932 (15)
H9A	−0.0357	0.5077	0.0738	0.112*
H9B	−0.0466	0.5979	0.1459	0.112*
C10	0.1646 (4)	0.6473 (6)	0.1389 (3)	0.0880 (13)
H10A	0.1219	0.7451	0.1504	0.106*
H10B	0.1631	0.6528	0.0876	0.106*
C11	0.2881 (4)	0.6607 (6)	0.1822 (2)	0.0713 (10)
H11A	0.2915	0.6441	0.2334	0.086*
H4N	0.3338	0.5716	0.1669	0.086*
C12	0.3349 (4)	0.8321 (5)	0.1708 (2)	0.0725 (11)
H12A	0.3294	0.8485	0.1195	0.087*
H12B	0.2888	0.9201	0.1865	0.087*
C13	−0.0732 (7)	0.0324 (9)	0.1558 (5)	0.151 (3)
H13A	−0.0359	−0.0697	0.1430	0.182*
H13B	−0.0489	0.0458	0.2079	0.182*
C14	−0.1959 (7)	0.0022 (10)	0.1373 (3)	0.129 (3)
H14A	−0.2341	0.1056	0.1479	0.155*
H14B	−0.2130	−0.0889	0.1680	0.155*
C15	−0.2442 (5)	−0.0463 (8)	0.0594 (3)	0.1042 (18)
H15A	−0.2385	0.0503	0.0281	0.125*
H15B	−0.2012	−0.1416	0.0461	0.125*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ge1	0.0602 (2)	0.03395 (18)	0.02960 (17)	0.00094 (13)	0.01036 (13)	0.00344 (11)
S1	0.0626 (5)	0.0634 (5)	0.0388 (4)	0.0157 (4)	0.0166 (3)	0.0086 (3)
S2	0.0973 (7)	0.0428 (4)	0.0406 (4)	−0.0147 (4)	0.0140 (4)	0.0072 (3)
S3	0.0768 (6)	0.0487 (5)	0.0396 (4)	−0.0091 (4)	0.0046 (4)	−0.0021 (3)
N1	0.066 (2)	0.0546 (18)	0.111 (3)	0.0014 (16)	0.0225 (19)	−0.0006 (19)
N2	0.076 (2)	0.062 (2)	0.152 (4)	−0.0009 (19)	−0.008 (3)	−0.010 (3)
N3	0.099 (2)	0.0472 (16)	0.0448 (15)	−0.0004 (16)	0.0211 (15)	−0.0012 (12)
N4	0.102 (3)	0.068 (2)	0.066 (2)	−0.0073 (19)	0.0226 (19)	−0.0058 (17)
C6	0.077 (3)	0.074 (3)	0.216 (7)	0.006 (3)	0.040 (4)	−0.035 (4)
C7	0.078 (3)	0.062 (3)	0.271 (10)	0.010 (3)	−0.014 (5)	−0.027 (4)
C8	0.068 (3)	0.083 (3)	0.138 (5)	−0.008 (2)	0.012 (3)	−0.011 (3)
C9	0.073 (3)	0.066 (3)	0.136 (5)	0.013 (2)	0.014 (3)	0.002 (3)
C10	0.088 (3)	0.068 (3)	0.109 (4)	0.005 (2)	0.026 (3)	0.013 (3)
C11	0.074 (2)	0.075 (3)	0.066 (2)	0.000 (2)	0.0193 (19)	−0.001 (2)
C12	0.101 (3)	0.058 (2)	0.056 (2)	0.014 (2)	0.014 (2)	−0.0031 (18)
C13	0.147 (6)	0.091 (4)	0.185 (8)	−0.047 (4)	−0.022 (6)	0.026 (5)
C14	0.157 (6)	0.136 (5)	0.086 (4)	−0.068 (5)	0.012 (4)	0.015 (4)
C15	0.107 (4)	0.128 (5)	0.079 (3)	−0.018 (3)	0.025 (3)	0.004 (3)

Geometric parameters (Å, º) top

Ge1—S3	2.1573 (9)	C7—H7B	0.9700
Ge1—S2	2.1669 (9)	C8—C9	1.485 (7)
Ge1—S1	2.2770 (9)	C8—H8A	0.9700
S1—Ge1ⁱ	2.2564 (8)	C8—H8B	0.9700
N1—C10	1.448 (6)	C9—H9A	0.9700
N1—C6	1.450 (6)	C9—H9B	0.9700
N1—C9	1.476 (6)	C10—C11	1.522 (6)
N2—C8	1.435 (7)	C10—H10A	0.9700
N2—C7	1.465 (7)	C10—H10B	0.9700
N2—C13	1.509 (8)	C11—C12	1.482 (6)
N3—C12	1.442 (5)	C11—H11A	0.9700
N3—H3A	0.8900	C11—H4N	0.9700
N3—H3B	0.8900	C12—H12A	0.9700
N3—H3C	0.8900	C12—H12B	0.9700
N4—C15	1.443 (7)	C13—C14	1.451 (10)
N4—H4A	0.8900	C13—H13A	0.9700
N4—H4B	0.8900	C13—H13B	0.9700
N4—H4C	0.8900	C14—C15	1.504 (8)
C6—C7	1.460 (8)	C14—H14A	0.9700
C6—H6A	0.9700	C14—H14B	0.9700
C6—H6B	0.9700	C15—H15A	0.9700
C7—H7A	0.9700	C15—H15B	0.9700

S3—Ge1—S2	114.15 (3)	N1—C9—C8	110.6 (4)
S3—Ge1—S1ⁱ	111.71 (4)	N1—C9—H9A	109.5
S2—Ge1—S1ⁱ	112.13 (4)	C8—C9—H9A	109.5
S3—Ge1—S1	112.70 (4)	N1—C9—H9B	109.5
S2—Ge1—S1	110.66 (4)	C8—C9—H9B	109.5
S1ⁱ—Ge1—S1	93.82 (3)	H9A—C9—H9B	108.1
Ge1ⁱ—S1—Ge1	86.18 (3)	N1—C10—C11	113.1 (4)
C10—N1—C6	112.7 (4)	N1—C10—H10A	109.0
C10—N1—C9	112.6 (4)	C11—C10—H10A	109.0
C6—N1—C9	106.5 (4)	N1—C10—H10B	109.0
C8—N2—C7	110.4 (4)	C11—C10—H10B	109.0
C8—N2—C13	109.1 (6)	H10A—C10—H10B	107.8
C7—N2—C13	109.2 (5)	C12—C11—C10	109.7 (4)
C12—N3—H3A	109.5	C12—C11—H11A	109.7
C12—N3—H3B	109.5	C10—C11—H11A	109.7
H3A—N3—H3B	109.5	C12—C11—H4N	109.7
C12—N3—H3C	109.5	C10—C11—H4N	109.7
H3A—N3—H3C	109.5	H11A—C11—H4N	108.2
H3B—N3—H3C	109.5	N3—C12—C11	112.7 (3)
C15—N4—H4A	109.5	N3—C12—H12A	109.1
C15—N4—H4B	109.5	C11—C12—H12A	109.1
H4A—N4—H4B	109.5	N3—C12—H12B	109.1
C15—N4—H4C	109.5	C11—C12—H12B	109.1
H4A—N4—H4C	109.5	H12A—C12—H12B	107.8
H4B—N4—H4C	109.5	C14—C13—N2	117.1 (6)
N1—C6—C7	111.8 (5)	C14—C13—H13A	108.0
N1—C6—H6A	109.3	N2—C13—H13A	108.0
C7—C6—H6A	109.3	C14—C13—H13B	108.0
N1—C6—H6B	109.3	N2—C13—H13B	108.0
C7—C6—H6B	109.3	H13A—C13—H13B	107.3
H6A—C6—H6B	107.9	C13—C14—C15	114.5 (7)
C6—C7—N2	114.2 (5)	C13—C14—H14A	108.6
C6—C7—H7A	108.7	C15—C14—H14A	108.6
N2—C7—H7A	108.7	C13—C14—H14B	108.6
C6—C7—H7B	108.7	C15—C14—H14B	108.6
N2—C7—H7B	108.7	H14A—C14—H14B	107.6
H7A—C7—H7B	107.6	N4—C15—C14	108.9 (5)
N2—C8—C9	112.9 (5)	N4—C15—H15A	109.9
N2—C8—H8A	109.0	C14—C15—H15A	109.9
C9—C8—H8A	109.0	N4—C15—H15B	109.9
N2—C8—H8B	109.0	C14—C15—H15B	109.9
C9—C8—H8B	109.0	H15A—C15—H15B	108.3
H8A—C8—H8B	107.8

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···S2ⁱⁱ	0.89	2.48	3.278 (3)	149
N3—H3C···S3	0.89	2.34	3.225 (3)	170
N3—H3A···S2ⁱⁱⁱ	0.89	2.61	3.440 (3)	157
N3—H3A···S3ⁱⁱⁱ	0.89	2.83	3.366 (3)	120
N4—H4C···S2^iv	0.89	2.53	3.408 (4)	169
N4—H4B···S2^v	0.89	2.34	3.228 (4)	178
N4—H4A···S3^vi	0.89	2.39	3.275 (4)	173

Symmetry codes: (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2; (iv) x−1, y, z; (v) −x, −y, −z; (vi) x−1, y−1, z.

Experimental details

Crystal data
Chemical formula	(C₁₀H₂₆N₄)₂[Ge₂S₆]
M_r	742.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.0111 (4), 7.7759 (3), 18.9777 (7)
β (°)	103.569 (1)
V (Å³)	1722.99 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.13
Crystal size (mm)	0.38 × 0.29 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.498, 0.727
No. of measured, independent and observed [I > 2σ(I)] reflections	16480, 3950, 3194
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.113, 1.07
No. of reflections	3950
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.15, −0.36

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
N3—H3B···S2ⁱ	0.89	2.48	3.278 (3)	149
N3—H3C···S3	0.89	2.34	3.225 (3)	170
N3—H3A···S2ⁱⁱ	0.89	2.61	3.440 (3)	157
N3—H3A···S3ⁱⁱ	0.89	2.83	3.366 (3)	120
N4—H4C···S2ⁱⁱⁱ	0.89	2.53	3.408 (4)	169
N4—H4B···S2^iv	0.89	2.34	3.228 (4)	178
N4—H4A···S3^v	0.89	2.39	3.275 (4)	173

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

Acknowledgements

This project was supported by the Program for New Century Excellent Talents in Universities of China (grant No. NCET-08–0618).

References

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