catena-Poly[silver(I)-bis­[μ-4-methyl-1H-1,2,4-triazole-3(4H)-thione-κ2S:S]-silver(I)-di-μ-thio­cyanato-κ2S:N;κ2N:S]

Kodcharat, K.; Pakawatchai, C.; Saithong, S.

doi:10.1107/S160053681300946X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Pages m265-m266

https://doi.org/10.1107/S160053681300946X

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catena-Poly[silver(I)-bis[μ-4-methyl-1H-1,2,4-triazole-3(4H)-thione-κ²S:S]-silver(I)-di-μ-thiocyanato-κ²S:N;κ²N:S]

Kultida Kodcharat,^a Chaveng Pakawatchai ^a and Saowanit Saithong ^a ^*

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: saowanit.sa@psu.ac.th

(Received 5 April 2013; accepted 7 April 2013; online 13 April 2013)

In the title one-dimensional coordination polymer, [Ag₂(NCS)₂(C₃H₅N₃S)₂]_n, the Ag^I atom adopts a distorted tetrahedral AgNS₃ geometry. Adjacent Ag^I atoms in the [001] chain are alternately linked by pairs of bridging 4-methyl-1H-1,2,4-triazole-3(4H)-thione (Hmptrz) ligands (via their S atoms) and double thiocyanate bridges linking through both S and N atoms (μ-1,3-SCN). An intrachain N—H⋯N hydrogen bond occurs between the NH group of the triazole ring and the N atom of the thiocyanate bridging ligand. A (101) sheet structure arises from interchain S⋯N short contacts [3.239 (3) Å] involving the thiocyanate S atom and the triazole-ring N atom and possible very weak π–π stacking [centroid–centroid separation = 4.0762 (18) Å] between the triazole rings.

Related literature

For examples of complexes with multifunctional ligand donors, see: Zhang et al.(2009 ); Wang et al. (2011 ). For background to complexes containing derivatives of the 1,2,4-triazole ligand, see: Zhang et al. (1999 ); Jiang et al. (2011 ). For the thiocyanate bridging ligand, end-to-end mode, see: Vicente et al. (1997 ); Chen et al. (1999 ); Diaz et al. (1999 ); Goher et al. (2000 ); Song et al. (2000 ); Cai et al. (2007 ); Saithong et al. (2007 ).

Experimental

Crystal data

[Ag₂(NCS)₂(C₃H₅N₃S)₂]
M_r = 562.22
Triclinic, $[P \overline 1]$
a = 7.4842 (6) Å
b = 7.5420 (6) Å
c = 8.4262 (7) Å
α = 79.985 (2)°
β = 84.329 (2)°
γ = 64.508 (1)°
V = 422.62 (6) Å³
Z = 1
Mo Kα radiation
μ = 2.82 mm⁻¹
T = 293 K
0.31 × 0.12 × 0.05 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.682, T_max = 0.879
5887 measured reflections
2083 independent reflections
1904 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.070
S = 1.05
2083 reflections
104 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—N4ⁱ	2.354 (3)
Ag1—S2	2.4987 (8)
Ag1—S1	2.5554 (8)
Ag1—S1ⁱⁱ	2.6688 (8)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4ⁱ	0.86 (2)	2.10 (2)	2.954 (4)	171 (3)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681300946X/hb7066sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681300946X/hb7066Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681300946X/hb7066Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S160053681300946X/hb7066Isup4.mol

checkCIF report

Comment top

One of the active areas of meterial research is the coordination compounds of the metal ions with the multifunctional ligands leading to the structural diversities and properties (Zhang et al., 2009; Wang et al., 2011). For this work, we report the mixed ligands Ag(I) complex containg multidonor atoms, 4-methyl-1,2,4-triazole-3-thiol (Hmptrz) and thiocyanate ligands. The Hmptrz is one of 1,2,4-triazole derivative ligands - based heterocyclic thioamide containing thiol group which has three potential donor atoms. Both Hmptrz and thiocyanate group are amphidentate ligands, which can bind to the metal center with either the N or S atom or both of them (Zhang et al., 1999; Jiang et al., 2011).

The title complex exhibits a one-dimensional chain polymeric structure and the asymmetric unit consists of one Ag(I) atom, one Hmptrz molecule and one SCN^- anion. The chemical structure of this complex is shown in Scheme I and the crystal structure is depicted in Figure 1.

The Ag atom features a distorted tetrahedral environment with the range of angles from 101.00 (2) to 124.52 (3)^o. Each Ag is bonded by two µ₂-S-bridging atoms of two Hmptrz molecules with the distances of 2.5554 (8) and 2.6688 (8) Å. The other two coordination sites are occupied by S and N atoms from the different µ₂-1,3-SCN bridges coordinated as a pair alternating bidentate end to end fashion similar to those complexes of the same thiocyanate bridges (Chen et al., 1999; Diaz et al., 1999; Goher et al., 2000; Song et al., 2000; Cai et al., 2007; Saithong et al. 2007). The Cu—S_thiocyanato and Cu—N_thiocyanato bond distances are 2.4987 (8) and 2.2354 (4) Å, respectively. The SCN bond angle is almost perfectly linear [178.6 (3)°] as compare with the same µ₂-1,3-SCN configuration mode of those complexes (Vicente et al.,1997; Song et al., 2000). The S2—C4 and C4—N4 distances [1.646 (3) and 1.150 (4) Å] refer to thiocyanate resonance form which indicate to a π-delocalized system along the metal-thiocyanate chain (Zhang et al., 1999).

An infintite one-dimensional structure of this complex is based on [Ag(µ_2-Hmptrz)(µ₂-1,3-SCN)] double-bridges, in which both Hmptrz and SCN^- ligands adopt the µ₂-end-on and µ₂-end-to-end bridging mode, respectively. As illustated in Figure 2, the Hmptrz and thiocyanato ligands interconnect the Ag(I) ions into an infinite chain generated by the unit c translation runing parallel to c axis, which consist of four-membered ring [—Ag—S—Ag—S—] and eight-membered ring [—Ag—S═C═N—Ag—S═C═N—]. In addition, The Ag···Ag separation with the distances of 3.3241 (5) Å in the four-membered ring is slighty shorter than the sum of the van der Waals radii of Ag atoms (3.44 Å), which indicates that there is the Ag···Ag interaction.

The weak intra-molecular hydrogen bonding interaction [N1—H1···N4ⁱ, (i) = -x + 1, -y, -z + 1] is found between N(1) of triazole ring and N(4) of thiocyanate bridging ligand at 2.954 (4) Å. The inter-short contact at 3.239 (3) Å arises from S2 donor of triazole ring with N2 acceptor from the thiocyanate bridge of the neighbouring adjacent chain which is smaller than the sum of S and N van der Waals radii (1.80 + 1.55 Å). In addition, the π···π stacking between the triazole rings of the neighbouring chain is observed with the centroid-centriod distance of 4.0762 (18) Å. Both of these interactions generate the supramolecular layer interactions related by ac-plane. A view of intra-molecular hydrogen bonding is depected in Figure 3 and The layered network interactions in crystal packing are shown in Figure 4.

Related literature top

For examples of complexes with multifunctional ligand donors, see: Zhang et al.(2009); Wang et al. (2011). For background to complexes containing derivatives of the 1,2,4-triazole ligand, see: Zhang et al. (1999); Jiang et al. (2011). For the thiocyanate bridging ligand, end-to-end mode, see: Vicente et al. (1997); Chen et al. (1999); Diaz et al. (1999); Goher et al. (2000); Song et al. (2000); Cai et al. (2007); Saithong et al. (2007).

Experimental top

A mixture of AgNO₃ (0.15 g, 0.88 mmol), KSCN (0.09 g, 0.87 mmol) in EtOH 30 ml was heated and stirred to 75 °C for 1 h. After that, the Hmptrz ligand (0.1 g, 0.087 mmol was added to the mixture and further continuous stirring for 12 h. The colorless crystals of the complex were obtained after the colorless filtrate was kept to stand at room temperature for a day. The complex melts at 130–132°C.

Structure description top

For examples of complexes with multifunctional ligand donors, see: Zhang et al.(2009); Wang et al. (2011). For background to complexes containing derivatives of the 1,2,4-triazole ligand, see: Zhang et al. (1999); Jiang et al. (2011). For the thiocyanate bridging ligand, end-to-end mode, see: Vicente et al. (1997); Chen et al. (1999); Diaz et al. (1999); Goher et al. (2000); Song et al. (2000); Cai et al. (2007); Saithong et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The structure of the title complex with displacement ellipsoids plotted at the 30% probability level.
	Fig. 2. The one-dimensional chain of the title complex.
	Fig. 3. The intra-chain hydrogen-bonding interactions of the title complex.
	Fig. 4. The two-dimensional-layer inter-interactions of the title complex. All H atoms not involving the interactions are omitted.

catena-Poly[silver(I)-bis[µ-4-methyl-1H-1,2,4-triazole-3(4H)-thione-κ²S:S]-silver(I)-di-µ-thiocyanato-κ²S:N;κ²N:S] top

Crystal data top

[Ag₂(NCS)₂(C₃H₅N₃S)₂]	Z = 1
M_r = 562.22	F(000) = 272
Triclinic, P1	D_x = 2.209 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4842 (6) Å	Cell parameters from 3160 reflections
b = 7.5420 (6) Å	θ = 2.5–28.1°
c = 8.4262 (7) Å	µ = 2.82 mm⁻¹
α = 79.985 (2)°	T = 293 K
β = 84.329 (2)°	Block, colourless
γ = 64.508 (1)°	0.31 × 0.12 × 0.05 mm
V = 422.62 (6) Å³

Data collection top

Bruker APEX CCD diffractometer	2083 independent reflections
Radiation source: fine-focus sealed tube	1904 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Frames, each covering 0.3 ° in ω scans	θ_max = 28.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −9→9
T_min = 0.682, T_max = 0.879	k = −10→10
5887 measured reflections	l = −11→11

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0262P)² + 0.3652P] where P = (F_o² + 2F_c²)/3
2083 reflections	(Δ/σ)_max < 0.001
104 parameters	Δρ_max = 0.79 e Å⁻³
1 restraint	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Ag₂(NCS)₂(C₃H₅N₃S)₂]	γ = 64.508 (1)°
M_r = 562.22	V = 422.62 (6) Å³
Triclinic, P1	Z = 1
a = 7.4842 (6) Å	Mo Kα radiation
b = 7.5420 (6) Å	µ = 2.82 mm⁻¹
c = 8.4262 (7) Å	T = 293 K
α = 79.985 (2)°	0.31 × 0.12 × 0.05 mm
β = 84.329 (2)°

Data collection top

Bruker APEX CCD diffractometer	2083 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	1904 reflections with I > 2σ(I)
T_min = 0.682, T_max = 0.879	R_int = 0.026
5887 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	1 restraint
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.79 e Å⁻³
2083 reflections	Δρ_min = −0.63 e Å⁻³
104 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
Ag1	0.43439 (4)	0.06942 (4)	0.18148 (3)	0.06373 (11)
S1	0.45768 (10)	0.28186 (11)	−0.08435 (10)	0.04902 (17)
N1	0.8089 (4)	0.2218 (4)	0.0367 (3)	0.0471 (5)
H1	0.784 (5)	0.168 (5)	0.130 (3)	0.057*
N2	0.9737 (4)	0.2569 (4)	−0.0040 (3)	0.0580 (7)
N3	0.7724 (3)	0.3598 (3)	−0.2066 (3)	0.0443 (5)
C1	0.6839 (4)	0.2840 (4)	−0.0829 (3)	0.0399 (5)
C2	0.9452 (4)	0.3410 (5)	−0.1505 (4)	0.0548 (7)
H2	1.0329	0.3844	−0.2120	0.066*
C3	0.6939 (6)	0.4444 (6)	−0.3672 (4)	0.0614 (8)
H3A	0.6677	0.3493	−0.4116	0.092*
H3B	0.7889	0.4779	−0.4352	0.092*
H3C	0.5733	0.5619	−0.3608	0.092*
S2	0.13129 (11)	0.14847 (14)	0.36025 (10)	0.0576 (2)
C4	0.2341 (4)	0.0469 (5)	0.5367 (4)	0.0479 (6)
N4	0.3024 (4)	−0.0245 (5)	0.6610 (3)	0.0661 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.06481 (18)	0.0881 (2)	0.05807 (16)	−0.04888 (16)	0.01183 (12)	−0.02344 (13)
S1	0.0410 (4)	0.0516 (4)	0.0602 (4)	−0.0237 (3)	−0.0010 (3)	−0.0116 (3)
N1	0.0437 (12)	0.0499 (13)	0.0494 (13)	−0.0240 (11)	−0.0036 (10)	0.0014 (10)
N2	0.0431 (13)	0.0646 (16)	0.0680 (17)	−0.0281 (12)	−0.0086 (12)	0.0049 (13)
N3	0.0451 (12)	0.0457 (12)	0.0454 (12)	−0.0225 (10)	0.0004 (9)	−0.0069 (10)
C1	0.0400 (13)	0.0357 (12)	0.0466 (13)	−0.0172 (10)	0.0015 (10)	−0.0107 (10)
C2	0.0427 (15)	0.0599 (18)	0.0645 (19)	−0.0275 (14)	−0.0007 (13)	−0.0007 (15)
C3	0.073 (2)	0.072 (2)	0.0447 (15)	−0.0374 (18)	−0.0050 (15)	−0.0028 (14)
S2	0.0427 (4)	0.0772 (5)	0.0541 (4)	−0.0308 (4)	−0.0013 (3)	0.0023 (4)
C4	0.0431 (14)	0.0621 (17)	0.0496 (15)	−0.0326 (13)	0.0082 (12)	−0.0135 (13)
N4	0.0619 (17)	0.100 (2)	0.0501 (15)	−0.0486 (17)	−0.0010 (13)	−0.0081 (15)

Geometric parameters (Å, º) top

Ag1—N4ⁱ	2.354 (3)	N3—C1	1.354 (3)
Ag1—S2	2.4987 (8)	N3—C2	1.363 (4)
Ag1—S1	2.5554 (8)	N3—C3	1.455 (4)
Ag1—S1ⁱⁱ	2.6688 (8)	C2—H2	0.9300
Ag1—Ag1ⁱⁱ	3.3241 (5)	C3—H3A	0.9600
S1—C1	1.701 (3)	C3—H3B	0.9600
S1—Ag1ⁱⁱ	2.6688 (8)	C3—H3C	0.9600
N1—C1	1.325 (3)	S2—C4	1.646 (3)
N1—N2	1.369 (3)	C4—N4	1.150 (4)
N1—H1	0.860 (18)	N4—Ag1ⁱ	2.354 (3)
N2—C2	1.278 (4)

N4ⁱ—Ag1—S2	107.73 (7)	C1—N3—C3	125.5 (2)
N4ⁱ—Ag1—S1	106.91 (7)	C2—N3—C3	127.7 (3)
S2—Ag1—S1	124.52 (3)	N1—C1—N3	104.4 (2)
N4ⁱ—Ag1—S1ⁱⁱ	104.55 (9)	N1—C1—S1	129.2 (2)
S2—Ag1—S1ⁱⁱ	110.41 (3)	N3—C1—S1	126.3 (2)
S1—Ag1—S1ⁱⁱ	101.00 (2)	N2—C2—N3	112.6 (3)
N4ⁱ—Ag1—Ag1ⁱⁱ	115.17 (8)	N2—C2—H2	123.7
S2—Ag1—Ag1ⁱⁱ	135.70 (2)	N3—C2—H2	123.7
S1—Ag1—Ag1ⁱⁱ	52.010 (19)	N3—C3—H3A	109.5
S1ⁱⁱ—Ag1—Ag1ⁱⁱ	48.991 (18)	N3—C3—H3B	109.5
C1—S1—Ag1	104.45 (10)	H3A—C3—H3B	109.5
C1—S1—Ag1ⁱⁱ	99.55 (9)	N3—C3—H3C	109.5
Ag1—S1—Ag1ⁱⁱ	79.00 (2)	H3A—C3—H3C	109.5
C1—N1—N2	113.0 (2)	H3B—C3—H3C	109.5
C1—N1—H1	122 (2)	C4—S2—Ag1	100.04 (10)
N2—N1—H1	125 (2)	N4—C4—S2	178.6 (3)
C2—N2—N1	103.3 (2)	C4—N4—Ag1ⁱ	142.0 (2)
C1—N3—C2	106.7 (2)

N4ⁱ—Ag1—S1—C1	11.91 (13)	C3—N3—C1—S1	−3.5 (4)
S2—Ag1—S1—C1	138.45 (9)	Ag1—S1—C1—N1	−10.7 (3)
S1ⁱⁱ—Ag1—S1—C1	−97.15 (9)	Ag1ⁱⁱ—S1—C1—N1	−91.7 (3)
Ag1ⁱⁱ—Ag1—S1—C1	−97.15 (9)	Ag1—S1—C1—N3	172.3 (2)
N4ⁱ—Ag1—S1—Ag1ⁱⁱ	109.06 (9)	Ag1ⁱⁱ—S1—C1—N3	91.3 (2)
S2—Ag1—S1—Ag1ⁱⁱ	−124.40 (3)	N1—N2—C2—N3	−0.6 (4)
S1ⁱⁱ—Ag1—S1—Ag1ⁱⁱ	0.0	C1—N3—C2—N2	1.2 (4)
C1—N1—N2—C2	−0.2 (4)	C3—N3—C2—N2	−178.9 (3)
N2—N1—C1—N3	0.9 (3)	N4ⁱ—Ag1—S2—C4	−24.14 (14)
N2—N1—C1—S1	−176.7 (2)	S1—Ag1—S2—C4	−150.33 (11)
C2—N3—C1—N1	−1.2 (3)	S1ⁱⁱ—Ag1—S2—C4	89.46 (11)
C3—N3—C1—N1	178.9 (3)	Ag1ⁱⁱ—Ag1—S2—C4	141.07 (11)
C2—N3—C1—S1	176.4 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4ⁱ	0.86 (2)	2.10 (2)	2.954 (4)	171 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Ag₂(NCS)₂(C₃H₅N₃S)₂]
M_r	562.22
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4842 (6), 7.5420 (6), 8.4262 (7)
α, β, γ (°)	79.985 (2), 84.329 (2), 64.508 (1)
V (Å³)	422.62 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.82
Crystal size (mm)	0.31 × 0.12 × 0.05

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.682, 0.879
No. of measured, independent and observed [I > 2σ(I)] reflections	5887, 2083, 1904
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.070, 1.05
No. of reflections	2083
No. of parameters	104
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)	0.79, −0.63

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ag1—N4ⁱ	2.354 (3)	Ag1—S1	2.5554 (8)
Ag1—S2	2.4987 (8)	Ag1—S1ⁱⁱ	2.6688 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4ⁱ	0.860 (18)	2.101 (19)	2.954 (4)	171 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

Financial support from the Center of Excellent for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Ministry of Education, and Graduate School, Prince of Songkla University, are gratefully acknowledge.

References

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