catena-Poly[[(2-{[2-(dimethyl­ammonio)­eth­yl]imino­meth­yl}pyridine-κ2N,N′)bis­(thio­cyanato-κN)manganese(II)]-μ-thio­cyanato-κ2N:S]

Wang, J.; Zhu, W.; Li, J.

doi:10.1107/S1600536812032874

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page m1131

https://doi.org/10.1107/S1600536812032874

Open

access

catena-Poly[[(2-{[2-(dimethylammonio)ethyl]iminomethyl}pyridine-κ²N,N′)bis(thiocyanato-κN)manganese(II)]-μ-thiocyanato-κ²N:S]

Jun Wang,^a Wubiao Zhu ^a and Jichang Li ^a ^*

^aZhongshan Polytechnic, Zhongshan, Guangdong 528404, People's Republic of China
^*Correspondence e-mail: wangjun7203@126.com

(Received 16 July 2012; accepted 19 July 2012; online 28 July 2012)

In the title one-dimensional coordination polymer, [Mn(NCS)₃(C₁₀H₁₆N₃)]_n, the Mn^II atom is coordinated by an N,N′-bidentate Schiff base and four thiocyanate ligands in a distorted octahedral N₅S geometry. Bridging thiocyanate ligands interconnect adjacent [Mn(NCS)₂(C₁₀H₁₆N₃)] units, giving rise to helical chains extending along the b axis. The chains are further linked through N—H⋯S hydrogen bonds, leading to a three-dimensional supramolecular network.

Related literature

For the structure of Cu^II and Pt^I complexes of the same Schiff base, see: Hinman et al. (2000 ); Mukherjee et al. (2002 ).

Experimental

Crystal data

[Mn(NCS)₃(C₁₀H₁₆N₃)]
M_r = 407.44
Orthorhombic, P b c a
a = 8.5603 (12) Å
b = 11.0699 (15) Å
c = 37.346 (5) Å
V = 3539.0 (8) Å³
Z = 8
Mo Kα radiation
μ = 1.11 mm⁻¹
T = 296 K
0.25 × 0.19 × 0.11 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.770, T_max = 0.888
18847 measured reflections
3660 independent reflections
2397 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.098
S = 1.04
3660 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯S1ⁱ	0.87	2.47	3.294 (3)	159
Symmetry code: (i) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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/S1600536812032874/rz2792sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032874/rz2792Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812032874/rz2792Isup3.mol

checkCIF report

Comment top

The title compound (Fig. 1) was obtained upon complexation of the Schiff base N,N-dimethyl-N'-[(pyridin-2-yl)methylene]ethane-1,2-diamine with Mn(ClO₄)₂ and KNCS. Similarly to what observed in a related platinium(II) complex (Hinman et al., 2000), due to the protonation of the amine nitrogen atom the Schiff base acts as a bidentate ligand instead as tridentate (Mukherjee et al., 2002). The Mn(II) ion is in a distorted octahedral coordination environment, provided by an N,N'-bidentate Schiff base and four NCS ligands. The µ₂-isothiocyanato ligands interconnect the [Mn(NCS)₂(C₁₀H₁₆N₃)] units, giving rise to one-dimensional helical chains along the b axis. Adjacent helical chains are further connected via N—H···S hydrogen bonds (Table 1) into a three-dimensional supramolecular structure.

Related literature top

For the structure of Cu^II and Pt^I complexes of the same Schiff base, see: Hinman et al. (2000); Mukherjee et al. (2002).

Experimental top

A mixture of 2-pyridinecarboxaldehyde (0.107 g, 1 mmol) and N,N-dimethylethyldiamine (0.088 g, 1 mmol) in ethanol (5 ml) was refluxed for 2 h followed by addition of a solution of Mn(ClO₄)₂.6H₂O (0.362 g, 1 mmol) and KNCS (0.291, 3 mmol) in a minimum amount of water. The resulting solution was refluxed for 30 min, then set aside at room temperature. Crystals of the title compound suitable for X-ray analysis were obtained after few days on slow evaporation of the solvent.

Structure description top

For the structure of Cu^II and Pt^I complexes of the same Schiff base, see: Hinman et al. (2000); Mukherjee et al. (2002).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 with displacement ellipsoids drawn at the 50% probability level. Symmetry code: (i) 2.5-x, 0.5+y, z.

catena-Poly[[(2-{[2-(dimethylammonio)ethyl]iminomethyl}pyridine- κ²N,N')bis(thiocyanato-κN)manganese(II)]- µ-thiocyanato-κ²N:S] top

Crystal data top

[Mn(NCS)₃(C₁₀H₁₆N₃)]	F(000) = 1672
M_r = 407.44	D_x = 1.529 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3600 reflections
a = 8.5603 (12) Å	θ = 1.2–28.0°
b = 11.0699 (15) Å	µ = 1.11 mm⁻¹
c = 37.346 (5) Å	T = 296 K
V = 3539.0 (8) Å³	Block, yellow
Z = 8	0.25 × 0.19 × 0.11 mm

Data collection top

Bruker APEXII area-detector diffractometer	3660 independent reflections
Radiation source: fine-focus sealed tube	2397 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
φ and ω scan	θ_max = 26.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.770, T_max = 0.888	k = −13→12
18847 measured reflections	l = −46→44

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0371P)² + 0.1816P] where P = (F_o² + 2F_c²)/3
3660 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Mn(NCS)₃(C₁₀H₁₆N₃)]	V = 3539.0 (8) Å³
M_r = 407.44	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.5603 (12) Å	µ = 1.11 mm⁻¹
b = 11.0699 (15) Å	T = 296 K
c = 37.346 (5) Å	0.25 × 0.19 × 0.11 mm

Data collection top

Bruker APEXII area-detector diffractometer	3660 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2397 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.888	R_int = 0.076
18847 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
3660 reflections	Δρ_min = −0.35 e Å⁻³
210 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
C1	0.8026 (4)	1.0515 (3)	0.29186 (7)	0.0365 (7)
H1	0.8775	1.1075	0.2848	0.044*
C2	0.6523 (4)	1.0652 (3)	0.27924 (8)	0.0427 (8)
H2	0.6263	1.1293	0.2643	0.051*
C3	0.5419 (4)	0.9820 (3)	0.28924 (8)	0.0470 (9)
H3A	0.4396	0.9885	0.2811	0.056*
C4	0.5847 (4)	0.8885 (3)	0.31150 (8)	0.0390 (8)
H4	0.5115	0.8311	0.3185	0.047*
C5	0.7368 (4)	0.8806 (3)	0.32342 (7)	0.0328 (7)
C6	0.7882 (4)	0.7845 (3)	0.34732 (8)	0.0365 (8)
H6	0.7188	0.7237	0.3539	0.044*
C7	0.9714 (4)	0.6847 (3)	0.38312 (8)	0.0400 (8)
H7A	1.0726	0.6528	0.3762	0.048*
H7B	0.8954	0.6198	0.3818	0.048*
C8	0.9784 (4)	0.7345 (3)	0.42070 (8)	0.0381 (8)
H8A	1.0409	0.8076	0.4207	0.046*
H8B	0.8736	0.7561	0.4283	0.046*
C9	1.2174 (4)	0.6312 (3)	0.44276 (10)	0.0601 (11)
H9A	1.2693	0.7068	0.4469	0.090*
H9B	1.2399	0.6036	0.4189	0.090*
H9C	1.2538	0.5726	0.4598	0.090*
C10	1.0076 (5)	0.6853 (4)	0.48428 (8)	0.0679 (12)
H10A	1.0542	0.6297	0.5009	0.102*
H10B	0.8963	0.6854	0.4874	0.102*
H10C	1.0477	0.7650	0.4885	0.102*
C11	1.3790 (4)	0.8798 (3)	0.39279 (8)	0.0358 (7)
C12	0.9167 (4)	1.0407 (3)	0.41865 (10)	0.0411 (8)
C13	1.2401 (4)	1.1848 (3)	0.30617 (8)	0.0351 (7)
Mn1	1.07355 (5)	0.94723 (4)	0.344285 (12)	0.03482 (15)
N1	0.8468 (3)	0.9621 (2)	0.31373 (6)	0.0312 (6)
N2	0.9266 (3)	0.7830 (2)	0.35923 (6)	0.0335 (6)
N3	1.0459 (3)	0.6475 (2)	0.44693 (7)	0.0398 (7)
N4	1.2709 (3)	0.8875 (2)	0.37436 (7)	0.0469 (7)
N5	0.9625 (4)	1.0375 (2)	0.38952 (8)	0.0500 (8)
N6	1.1752 (3)	1.1042 (2)	0.31952 (7)	0.0447 (7)
H3	0.9996	0.5806	0.4412	0.067*
S1	1.53139 (11)	0.87179 (8)	0.41894 (2)	0.0482 (3)
S2	0.85784 (14)	1.04061 (10)	0.46007 (2)	0.0646 (3)
S3	1.32720 (10)	1.29615 (7)	0.28601 (2)	0.0427 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.040 (2)	0.0343 (18)	0.0352 (17)	0.0006 (15)	0.0050 (15)	0.0024 (15)
C2	0.045 (2)	0.042 (2)	0.0411 (19)	0.0111 (17)	−0.0011 (17)	0.0056 (16)
C3	0.037 (2)	0.060 (2)	0.044 (2)	0.0059 (18)	−0.0041 (17)	0.0013 (18)
C4	0.0304 (19)	0.044 (2)	0.0424 (19)	−0.0054 (15)	0.0004 (15)	0.0008 (16)
C5	0.0332 (19)	0.0328 (18)	0.0325 (17)	−0.0029 (14)	0.0030 (14)	−0.0017 (14)
C6	0.044 (2)	0.0306 (18)	0.0350 (17)	−0.0069 (14)	0.0037 (16)	0.0018 (14)
C7	0.050 (2)	0.0276 (17)	0.0426 (19)	0.0029 (15)	−0.0033 (16)	0.0048 (15)
C8	0.047 (2)	0.0307 (18)	0.0366 (18)	0.0059 (15)	−0.0006 (16)	0.0037 (14)
C9	0.048 (2)	0.067 (3)	0.065 (3)	0.003 (2)	−0.009 (2)	0.005 (2)
C10	0.094 (3)	0.078 (3)	0.032 (2)	−0.003 (2)	0.002 (2)	−0.006 (2)
C11	0.0377 (19)	0.0300 (18)	0.0398 (19)	−0.0024 (14)	0.0013 (16)	−0.0002 (15)
C12	0.038 (2)	0.0301 (18)	0.055 (2)	−0.0001 (15)	−0.0126 (18)	−0.0077 (17)
C13	0.0318 (19)	0.0372 (19)	0.0362 (17)	−0.0002 (14)	−0.0020 (15)	−0.0036 (15)
Mn1	0.0324 (3)	0.0317 (3)	0.0404 (3)	−0.0035 (2)	−0.0037 (2)	0.0040 (2)
N1	0.0315 (15)	0.0291 (14)	0.0328 (14)	0.0003 (11)	0.0012 (11)	0.0017 (12)
N2	0.0421 (17)	0.0280 (14)	0.0304 (14)	0.0007 (12)	−0.0001 (12)	0.0023 (11)
N3	0.0482 (19)	0.0363 (15)	0.0349 (14)	−0.0042 (13)	−0.0040 (13)	0.0010 (12)
N4	0.0424 (18)	0.0521 (18)	0.0463 (17)	−0.0019 (14)	−0.0078 (15)	−0.0031 (14)
N5	0.058 (2)	0.0441 (18)	0.0483 (18)	−0.0010 (14)	0.0039 (16)	−0.0054 (15)
N6	0.0447 (18)	0.0370 (16)	0.0525 (18)	−0.0050 (14)	0.0026 (14)	0.0029 (14)
S1	0.0476 (6)	0.0432 (5)	0.0538 (5)	0.0057 (4)	−0.0176 (4)	−0.0027 (4)
S2	0.0818 (8)	0.0664 (7)	0.0455 (6)	−0.0123 (6)	0.0038 (5)	−0.0092 (5)
S3	0.0478 (6)	0.0360 (5)	0.0442 (5)	−0.0086 (4)	0.0037 (4)	0.0034 (4)

Geometric parameters (Å, º) top

C1—N1	1.337 (3)	C9—H9A	0.9600
C1—C2	1.379 (4)	C9—H9B	0.9600
C1—H1	0.9300	C9—H9C	0.9600
C2—C3	1.371 (5)	C10—N3	1.492 (4)
C2—H2	0.9300	C10—H10A	0.9600
C3—C4	1.377 (4)	C10—H10B	0.9600
C3—H3A	0.9300	C10—H10C	0.9600
C4—C5	1.379 (4)	C11—N4	1.157 (4)
C4—H4	0.9300	C11—S1	1.632 (3)
C5—N1	1.354 (4)	C12—N5	1.157 (4)
C5—C6	1.457 (4)	C12—S2	1.627 (4)
C6—N2	1.266 (4)	C13—N6	1.162 (4)
C6—H6	0.9300	C13—S3	1.626 (3)
C7—N2	1.459 (3)	Mn1—N4	2.133 (3)
C7—C8	1.509 (4)	Mn1—N6	2.153 (3)
C7—H7A	0.9700	Mn1—N5	2.181 (3)
C7—H7B	0.9700	Mn1—N1	2.257 (2)
C8—N3	1.490 (4)	Mn1—N2	2.280 (2)
C8—H8A	0.9700	Mn1—S3ⁱ	2.8731 (10)
C8—H8B	0.9700	N3—H3	0.8675
C9—N3	1.487 (4)	S3—Mn1ⁱⁱ	2.8732 (10)

N1—C1—C2	123.6 (3)	H10A—C10—H10B	109.5
N1—C1—H1	118.2	N3—C10—H10C	109.5
C2—C1—H1	118.2	H10A—C10—H10C	109.5
C3—C2—C1	118.4 (3)	H10B—C10—H10C	109.5
C3—C2—H2	120.8	N4—C11—S1	178.9 (3)
C1—C2—H2	120.8	N5—C12—S2	177.5 (3)
C2—C3—C4	119.0 (3)	N6—C13—S3	177.7 (3)
C2—C3—H3A	120.5	N4—Mn1—N6	98.99 (11)
C4—C3—H3A	120.5	N4—Mn1—N5	94.55 (11)
C3—C4—C5	119.6 (3)	N6—Mn1—N5	98.00 (10)
C3—C4—H4	120.2	N4—Mn1—N1	165.80 (10)
C5—C4—H4	120.2	N6—Mn1—N1	94.10 (9)
N1—C5—C4	121.9 (3)	N5—Mn1—N1	89.04 (10)
N1—C5—C6	116.1 (3)	N4—Mn1—N2	93.50 (10)
C4—C5—C6	122.0 (3)	N6—Mn1—N2	166.41 (10)
N2—C6—C5	120.5 (3)	N5—Mn1—N2	86.27 (10)
N2—C6—H6	119.8	N1—Mn1—N2	72.99 (9)
C5—C6—H6	119.8	N4—Mn1—S3ⁱ	89.10 (8)
N2—C7—C8	107.8 (2)	N6—Mn1—S3ⁱ	91.43 (7)
N2—C7—H7A	110.1	N5—Mn1—S3ⁱ	169.22 (8)
C8—C7—H7A	110.1	N1—Mn1—S3ⁱ	85.06 (6)
N2—C7—H7B	110.1	N2—Mn1—S3ⁱ	83.38 (6)
C8—C7—H7B	110.1	C1—N1—C5	117.3 (3)
H7A—C7—H7B	108.5	C1—N1—Mn1	127.3 (2)
N3—C8—C7	113.0 (2)	C5—N1—Mn1	114.49 (19)
N3—C8—H8A	109.0	C6—N2—C7	118.1 (3)
C7—C8—H8A	109.0	C6—N2—Mn1	114.85 (19)
N3—C8—H8B	109.0	C7—N2—Mn1	126.8 (2)
C7—C8—H8B	109.0	C9—N3—C10	110.4 (3)
H8A—C8—H8B	107.8	C9—N3—C8	113.1 (3)
N3—C9—H9A	109.5	C10—N3—C8	110.4 (3)
N3—C9—H9B	109.5	C9—N3—H3	108.7
H9A—C9—H9B	109.5	C10—N3—H3	111.8
N3—C9—H9C	109.5	C8—N3—H3	102.2
H9A—C9—H9C	109.5	C11—N4—Mn1	165.9 (3)
H9B—C9—H9C	109.5	C12—N5—Mn1	152.9 (3)
N3—C10—H10A	109.5	C13—N6—Mn1	175.2 (3)
N3—C10—H10B	109.5	C13—S3—Mn1ⁱⁱ	103.08 (11)

N1—C1—C2—C3	−0.8 (5)	C5—C6—N2—Mn1	5.0 (4)
C1—C2—C3—C4	0.3 (5)	C8—C7—N2—C6	−104.8 (3)
C2—C3—C4—C5	0.3 (5)	C8—C7—N2—Mn1	69.3 (3)
C3—C4—C5—N1	−0.3 (5)	N4—Mn1—N2—C6	177.1 (2)
C3—C4—C5—C6	179.3 (3)	N6—Mn1—N2—C6	−26.1 (5)
N1—C5—C6—N2	3.2 (4)	N5—Mn1—N2—C6	82.8 (2)
C4—C5—C6—N2	−176.4 (3)	N1—Mn1—N2—C6	−7.4 (2)
N2—C7—C8—N3	−171.4 (3)	S3ⁱ—Mn1—N2—C6	−94.2 (2)
C2—C1—N1—C5	0.8 (4)	N4—Mn1—N2—C7	2.8 (2)
C2—C1—N1—Mn1	−167.9 (2)	N6—Mn1—N2—C7	159.5 (4)
C4—C5—N1—C1	−0.2 (4)	N5—Mn1—N2—C7	−91.6 (2)
C6—C5—N1—C1	−179.9 (2)	N1—Mn1—N2—C7	178.3 (2)
C4—C5—N1—Mn1	169.9 (2)	S3ⁱ—Mn1—N2—C7	91.4 (2)
C6—C5—N1—Mn1	−9.8 (3)	C7—C8—N3—C9	72.4 (4)
N4—Mn1—N1—C1	−163.6 (4)	C7—C8—N3—C10	−163.3 (3)
N6—Mn1—N1—C1	−6.4 (2)	N6—Mn1—N4—C11	48.5 (11)
N5—Mn1—N1—C1	91.5 (2)	N5—Mn1—N4—C11	−50.4 (11)
N2—Mn1—N1—C1	177.9 (2)	N1—Mn1—N4—C11	−154.6 (9)
S3ⁱ—Mn1—N1—C1	−97.5 (2)	N2—Mn1—N4—C11	−136.9 (11)
N4—Mn1—N1—C5	27.5 (5)	S3ⁱ—Mn1—N4—C11	139.8 (11)
N6—Mn1—N1—C5	−175.4 (2)	N4—Mn1—N5—C12	−50.7 (6)
N5—Mn1—N1—C5	−77.4 (2)	N6—Mn1—N5—C12	−150.4 (6)
N2—Mn1—N1—C5	8.97 (19)	N1—Mn1—N5—C12	115.6 (6)
S3ⁱ—Mn1—N1—C5	93.54 (19)	N2—Mn1—N5—C12	42.5 (6)
C5—C6—N2—C7	179.9 (2)	S3ⁱ—Mn1—N5—C12	58.8 (9)

Symmetry codes: (i) −x+5/2, y−1/2, z; (ii) −x+5/2, y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S1ⁱ	0.87	2.47	3.294 (3)	159

Symmetry code: (i) −x+5/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	[Mn(NCS)₃(C₁₀H₁₆N₃)]
M_r	407.44
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	8.5603 (12), 11.0699 (15), 37.346 (5)
V (Å³)	3539.0 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.11
Crystal size (mm)	0.25 × 0.19 × 0.11

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.770, 0.888
No. of measured, independent and observed [I > 2σ(I)] reflections	18847, 3660, 2397
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.098, 1.04
No. of reflections	3660
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.35

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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—H3···S1ⁱ	0.87	2.47	3.294 (3)	158.7

Symmetry code: (i) −x+5/2, y−1/2, z.

Acknowledgements

The work was supported by Zhongshan Polytechnic.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hinman, J. G., Baar, C. R., Jennings, M. C. & Puddephatt, R. J. (2000). Organometallics, 19, 563–570. Web of Science CSD CrossRef CAS Google Scholar
Mukherjee, P. S., Maji, T. K., Escuer, A., Vicente, R., Ribas, J., Rosair, G., Mautner, F. A. & Chaudhuri, N. R. (2002). Eur. J. Inorg. Chem. pp. 943–949. CSD CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.