{N,N′-Bis[1-(2-pyrid­yl)ethyl­idene]ethane-1,2-diamine-κ4N,N′,N′′,N′′′}(thio­cyanato-κN)zinc(II) perchlorate

Wang, F.-M.

doi:10.1107/S1600536810021628

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages m778-m779

doi:10.1107/S1600536810021628

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{N,N′-Bis[1-(2-pyridyl)ethylidene]ethane-1,2-diamine-κ⁴N,N′,N′′,N′′′}(thiocyanato-κN)zinc(II) perchlorate

Fu-Ming Wang ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou Shandong 253023, People's Republic of China
^*Correspondence e-mail: wfm99999@126.com

(Received 6 June 2010; accepted 7 June 2010; online 16 June 2010)

In the title compound, [Zn(NCS)(C₁₆H₁₈N₄)]ClO₄, the Zn^II atom is five-coordinated by four N atoms of the Schiff base ligand N,N′-bis[1-(2-pyridyl)ethylidene]ethane-1,2-diamine in the basal plane, and by the N atom of a thiocyanate ligand at the apical position, forming a distorted square-pyramidal geometry. The r.m.s. deviation from a plane through the four N atoms of the Schiff base is 0.015 (3) Å, and the deviation of the Ni atom from that plane is 0.591 (2) Å. Bond lengths are comparable with those observed in similar zinc(II) complexes with Schiff bases. The two methylene C atoms of the ethane-1,2-diamine bridge of the Schiff base ligand are disordered over two sites with occupancies of 0.587 (3) and 0.413 (3).

Related literature

For background to Schiff base compounds and their applications, see: Ruck & Jacobsen (2002 ); Mukhopadhyay et al. (2003 ); Polt et al. (2003 ); Mukherjee et al. (2001 ). For complexes derived from N,N′-bis(1-(pyridin-2-yl)ethylidene)ethane-1,2-diamine, see: Gourbatsis et al. (1998 ); Louloudi et al. (1999 ); Karmakar et al. (2002 ); Banerjee et al. (2004 ). For bond lengths in similar zinc(II) complexes with Schiff bases, see: Ghosh et al. (2006 ); Chen et al. (2005 ). For the synthesis of the Schiff base ligand, see: Gourbatsis et al. (1990 ).

Experimental

Crystal data

[Zn(NCS)(C₁₆H₁₈N₄)]ClO₄
M_r = 489.24
Monoclinic, P 2₁ /c
a = 8.685 (2) Å
b = 13.963 (3) Å
c = 17.374 (2) Å
β = 99.690 (3)°
V = 2076.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.45 mm⁻¹
T = 298 K
0.32 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.655, T_max = 0.671
16681 measured reflections
4529 independent reflections
2534 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.170
S = 1.02
4529 reflections
282 parameters
48 restraints
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N5	1.982 (5)
Zn1—N3	2.099 (4)
Zn1—N1	2.100 (4)
Zn1—N2	2.102 (4)
Zn1—N4	2.115 (4)

N5—Zn1—N3	109.08 (17)
N5—Zn1—N1	105.95 (16)
N3—Zn1—N1	141.17 (14)
N5—Zn1—N2	110.56 (19)
N3—Zn1—N2	75.37 (15)
N1—Zn1—N2	77.12 (15)
N5—Zn1—N4	101.91 (17)
N3—Zn1—N4	77.11 (14)
N1—Zn1—N4	111.48 (15)
N2—Zn1—N4	142.71 (17)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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 global, I. DOI: 10.1107/S1600536810021628/sj5017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021628/sj5017Isup2.hkl

checkCIF report

Comment top

Metal complexes with Schiff bases have been known since 1840. The Schiff bases and their complexes have played an important role in the development of coordination chemistry, biological and material sciences (Ruck & Jacobsen, 2002; Mukhopadhyay et al., 2003; Polt et al., 2003; Mukherjee et al., 2001). Several complexes derived from N,N'-bis(1-(pyridin-2-yl)ethylidene)ethane-1,2-diamine have been reported (Gourbatsis et al., 1998; Louloudi et al., 1999; Karmakar et al., 2002; Banerjee et al., 2004). In this paper, the title new zinc(II) complex is reported.

The title compound consists of a mononuclear zinc(II) complex cation and a perchlorate anion, Fig. 1. The Zn^II atom is five-coordinated by four N atoms of the Schiff base ligand N,N'-bis(1-(pyridin-2-yl)ethylidene)ethane-1,2-diamine, and by one N atom of a thiocyanate ligand, forming a square pyramidal geometry. The coordinate bond lengths (Table 1) are comparable to those observed in other similar zinc(II) complexes with Schiff bases (Ghosh et al., 2006; Chen et al., 2005).

Related literature top

For background to Schiff base compounds and their applications, see: Ruck & Jacobsen (2002); Mukhopadhyay et al. (2003); Polt et al. (2003); Mukherjee et al. (2001). For complexes derived from N,N'-bis(1-(pyridin-2-yl)ethylidene)ethane-1,2-diamine, see: Gourbatsis et al. (1998); Louloudi et al. (1999); Karmakar et al. (2002); Banerjee et al. (2004). For bond lengths in similar zinc(II) complexes with Schiff bases, see: Ghosh et al. (2006); Chen et al. (2005). For the synthesis of the Schiff base ligand, see: Gourbatsis et al. (1990).

Experimental top

The Schiff base ligand N,N'-bis(1-(pyridin-2-yl)ethylidene)ethane-1,2-diamine was synthesized according to the literature method (Gourbatsis et al., 1990). To a stirred methanol solution of the Schiff base ligand (1.0 mmol, 0.266 g) was added a methanol solution of zinc(II) perchlorate (1.0 mmol, 0.390 g) and ammonium thiocyanate (1.0 mmol, 0.076 g). The mixture was boiled under reflux for 2 h, then cooled to room temperature. Colourless block-like single crystals, suitable for X-ray diffraction, were formed after slow evaporation of the solution in air for a few days.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Only the major component of the disordered group is shown.

{N,N'-Bis[1-(2-pyridyl)ethylidene]ethane-1,2-diamine- κ⁴N,N',N'',N'''}(thiocyanato- κN)zinc(II) perchlorate top

Crystal data top

[Zn(NCS)(C₁₆H₁₈N₄)]ClO₄	F(000) = 1000
M_r = 489.24	D_x = 1.565 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2719 reflections
a = 8.685 (2) Å	θ = 2.4–25.0°
b = 13.963 (3) Å	µ = 1.45 mm⁻¹
c = 17.374 (2) Å	T = 298 K
β = 99.690 (3)°	Block, colourless
V = 2076.9 (7) Å³	0.32 × 0.30 × 0.30 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4529 independent reflections
Radiation source: fine-focus sealed tube	2534 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ω scan	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.655, T_max = 0.671	k = −17→16
16681 measured reflections	l = −22→22

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0792P)² + 0.7526P] where P = (F_o² + 2F_c²)/3
4529 reflections	(Δ/σ)_max < 0.001
282 parameters	Δρ_max = 0.50 e Å⁻³
48 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

[Zn(NCS)(C₁₆H₁₈N₄)]ClO₄	V = 2076.9 (7) Å³
M_r = 489.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.685 (2) Å	µ = 1.45 mm⁻¹
b = 13.963 (3) Å	T = 298 K
c = 17.374 (2) Å	0.32 × 0.30 × 0.30 mm
β = 99.690 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4529 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2534 reflections with I > 2σ(I)
T_min = 0.655, T_max = 0.671	R_int = 0.056
16681 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	48 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.02	Δρ_max = 0.50 e Å⁻³
4529 reflections	Δρ_min = −0.66 e Å⁻³
282 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	Occ. (<1)
Zn1	0.40268 (7)	0.18336 (3)	0.23821 (3)	0.0532 (2)
Cl1	0.13446 (17)	0.32198 (10)	0.93392 (9)	0.0761 (4)
S1	0.80304 (19)	0.18105 (12)	0.08648 (10)	0.0888 (5)
O1	0.1863 (9)	0.2376 (4)	0.9693 (3)	0.170 (3)
O2	0.2281 (6)	0.3965 (4)	0.9651 (3)	0.145 (2)
O3	0.1346 (6)	0.3155 (3)	0.8524 (2)	0.0975 (14)
O4	−0.0172 (5)	0.3397 (4)	0.9480 (3)	0.1246 (19)
N1	0.2700 (4)	0.3093 (2)	0.2175 (2)	0.0516 (9)
N4	0.2661 (4)	0.0604 (3)	0.2040 (2)	0.0547 (10)
N5	0.5483 (6)	0.1840 (3)	0.1618 (3)	0.0725 (13)
C1	0.1666 (6)	0.3311 (4)	0.1535 (3)	0.0640 (13)
H1	0.1435	0.2853	0.1144	0.077*
C2	0.0928 (6)	0.4194 (4)	0.1434 (3)	0.0724 (15)
H2	0.0234	0.4328	0.0978	0.087*
C3	0.1231 (7)	0.4857 (4)	0.2009 (4)	0.0762 (16)
H3	0.0728	0.5447	0.1959	0.091*
C4	0.2296 (6)	0.4645 (3)	0.2672 (3)	0.0673 (14)
H4	0.2531	0.5097	0.3067	0.081*
C5	0.3015 (6)	0.3754 (3)	0.2744 (3)	0.0524 (11)
C6	0.4210 (6)	0.3474 (3)	0.3435 (3)	0.0608 (13)
C7	0.4484 (8)	0.4109 (4)	0.4138 (3)	0.0881 (19)
H7A	0.3514	0.4216	0.4320	0.132*
H7B	0.4902	0.4710	0.4003	0.132*
H7C	0.5212	0.3808	0.4543	0.132*
N2	0.4901 (5)	0.2687 (3)	0.3355 (3)	0.0713 (12)	0.59 (3)
N3	0.4830 (4)	0.0850 (3)	0.3273 (2)	0.0537 (10)	0.59 (3)
C8	0.573 (2)	0.2217 (8)	0.4079 (7)	0.076 (4)	0.59 (3)
H8A	0.5077	0.2231	0.4481	0.092*	0.59 (3)
H8B	0.6691	0.2557	0.4272	0.092*	0.59 (3)
C9	0.6085 (18)	0.1192 (11)	0.3889 (10)	0.073 (6)	0.59 (3)
H9A	0.7083	0.1159	0.3709	0.088*	0.59 (3)
H9B	0.6141	0.0795	0.4351	0.088*	0.59 (3)
N2'	0.4901 (5)	0.2687 (3)	0.3355 (3)	0.0713 (12)	0.41 (3)
N3'	0.4830 (4)	0.0850 (3)	0.3273 (2)	0.0537 (10)	0.41 (3)
C8'	0.6313 (16)	0.2226 (10)	0.3782 (13)	0.058 (5)	0.41 (3)
H8'A	0.6739	0.2587	0.4247	0.070*	0.41 (3)
H8'B	0.7109	0.2158	0.3456	0.070*	0.41 (3)
C9'	0.571 (3)	0.1262 (15)	0.3990 (8)	0.058 (6)	0.41 (3)
H9'A	0.6570	0.0846	0.4201	0.070*	0.41 (3)
H9'B	0.5035	0.1335	0.4379	0.070*	0.41 (3)
C10	0.4124 (6)	0.0058 (3)	0.3271 (3)	0.0531 (12)
C11	0.4348 (8)	−0.0665 (4)	0.3924 (3)	0.0878 (19)
H11A	0.5251	−0.0497	0.4299	0.132*
H11B	0.4493	−0.1290	0.3716	0.132*
H11C	0.3442	−0.0670	0.4174	0.132*
C12	0.2956 (5)	−0.0134 (3)	0.2555 (3)	0.0518 (11)
C13	0.2222 (6)	−0.1010 (4)	0.2399 (3)	0.0714 (15)
H13	0.2424	−0.1509	0.2756	0.086*
C14	0.1198 (7)	−0.1136 (4)	0.1718 (4)	0.089 (2)
H14	0.0677	−0.1716	0.1614	0.107*
C15	0.0947 (7)	−0.0406 (5)	0.1193 (4)	0.093 (2)
H15	0.0289	−0.0491	0.0717	0.112*
C16	0.1684 (6)	0.0465 (4)	0.1376 (3)	0.0775 (16)
H16	0.1487	0.0968	0.1022	0.093*
C17	0.6548 (7)	0.1821 (3)	0.1302 (3)	0.0544 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0591 (4)	0.0415 (3)	0.0582 (4)	−0.0002 (3)	0.0079 (3)	0.0004 (2)
Cl1	0.0691 (9)	0.0799 (10)	0.0767 (9)	−0.0045 (8)	0.0053 (7)	−0.0098 (8)
S1	0.0678 (10)	0.1090 (13)	0.0936 (12)	0.0072 (9)	0.0252 (9)	0.0140 (9)
O1	0.247 (6)	0.129 (4)	0.128 (4)	0.090 (4)	0.019 (4)	0.038 (4)
O2	0.128 (4)	0.170 (5)	0.139 (4)	−0.084 (4)	0.031 (3)	−0.071 (4)
O3	0.117 (3)	0.115 (3)	0.063 (2)	−0.004 (3)	0.023 (2)	−0.015 (2)
O4	0.054 (3)	0.207 (6)	0.119 (4)	0.000 (3)	0.031 (3)	−0.013 (3)
N1	0.058 (2)	0.045 (2)	0.052 (2)	0.0013 (18)	0.0111 (18)	0.0031 (17)
N4	0.050 (2)	0.050 (2)	0.062 (2)	0.0005 (18)	0.0044 (19)	−0.0043 (19)
N5	0.088 (3)	0.055 (3)	0.080 (3)	0.003 (2)	0.032 (3)	0.009 (2)
C1	0.072 (3)	0.062 (3)	0.057 (3)	0.003 (3)	0.009 (3)	0.001 (2)
C2	0.077 (4)	0.062 (3)	0.077 (4)	0.018 (3)	0.008 (3)	0.017 (3)
C3	0.085 (4)	0.058 (3)	0.088 (4)	0.022 (3)	0.017 (3)	0.013 (3)
C4	0.076 (4)	0.043 (3)	0.086 (4)	0.001 (3)	0.024 (3)	−0.005 (3)
C5	0.057 (3)	0.045 (3)	0.058 (3)	−0.009 (2)	0.018 (2)	0.001 (2)
C6	0.068 (3)	0.043 (3)	0.069 (3)	−0.012 (2)	0.002 (3)	−0.001 (2)
C7	0.115 (5)	0.061 (3)	0.079 (4)	−0.008 (3)	−0.009 (3)	−0.017 (3)
N2	0.064 (3)	0.053 (3)	0.088 (3)	−0.001 (2)	−0.015 (2)	−0.004 (2)
N3	0.055 (2)	0.049 (2)	0.055 (2)	−0.0005 (19)	0.0049 (18)	−0.0021 (18)
C8	0.073 (8)	0.071 (6)	0.080 (7)	−0.002 (5)	−0.002 (6)	−0.008 (5)
C9	0.080 (9)	0.063 (8)	0.071 (8)	0.004 (6)	−0.003 (6)	−0.007 (5)
N2'	0.064 (3)	0.053 (3)	0.088 (3)	−0.001 (2)	−0.015 (2)	−0.004 (2)
N3'	0.055 (2)	0.049 (2)	0.055 (2)	−0.0005 (19)	0.0049 (18)	−0.0021 (18)
C8'	0.044 (7)	0.058 (7)	0.069 (8)	−0.001 (6)	0.001 (6)	−0.010 (6)
C9'	0.068 (9)	0.051 (9)	0.051 (8)	0.005 (7)	−0.003 (7)	0.004 (6)
C10	0.065 (3)	0.039 (2)	0.057 (3)	0.008 (2)	0.017 (2)	0.000 (2)
C11	0.129 (6)	0.055 (3)	0.076 (4)	−0.006 (3)	0.008 (4)	0.009 (3)
C12	0.048 (3)	0.043 (3)	0.068 (3)	0.004 (2)	0.020 (2)	−0.007 (2)
C13	0.065 (4)	0.050 (3)	0.098 (4)	−0.007 (3)	0.013 (3)	−0.006 (3)
C14	0.076 (4)	0.058 (4)	0.129 (6)	−0.015 (3)	0.001 (4)	−0.021 (4)
C15	0.077 (4)	0.085 (5)	0.104 (5)	−0.011 (4)	−0.023 (4)	−0.023 (4)
C16	0.071 (4)	0.069 (4)	0.084 (4)	0.001 (3)	−0.011 (3)	−0.004 (3)
C17	0.065 (3)	0.038 (2)	0.058 (3)	0.001 (2)	0.002 (3)	0.007 (2)

Geometric parameters (Å, º) top

Zn1—N5	1.982 (5)	C7—H7C	0.9600
Zn1—N3	2.099 (4)	N2—C8	1.492 (8)
Zn1—N1	2.100 (4)	N3—C10	1.264 (5)
Zn1—N2	2.102 (4)	N3—C9	1.472 (8)
Zn1—N4	2.115 (4)	C8—C9	1.513 (10)
Cl1—O1	1.370 (5)	C8—H8A	0.9700
Cl1—O2	1.374 (4)	C8—H8B	0.9700
Cl1—O4	1.401 (4)	C9—H9A	0.9700
Cl1—O3	1.419 (4)	C9—H9B	0.9700
S1—C17	1.601 (6)	C8'—C9'	1.512 (10)
N1—C1	1.340 (6)	C8'—H8'A	0.9700
N1—C5	1.347 (5)	C8'—H8'B	0.9700
N4—C16	1.327 (6)	C9'—H9'A	0.9700
N4—C12	1.359 (6)	C9'—H9'B	0.9700
N5—C17	1.153 (7)	C10—C12	1.492 (6)
C1—C2	1.387 (7)	C10—C11	1.508 (7)
C1—H1	0.9300	C11—H11A	0.9600
C2—C3	1.355 (7)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11C	0.9600
C3—C4	1.382 (7)	C12—C13	1.385 (6)
C3—H3	0.9300	C13—C14	1.368 (8)
C4—C5	1.388 (6)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.360 (8)
C5—C6	1.501 (7)	C14—H14	0.9300
C6—N2	1.271 (6)	C15—C16	1.387 (7)
C6—C7	1.495 (7)	C15—H15	0.9300
C7—H7A	0.9600	C16—H16	0.9300
C7—H7B	0.9600

N5—Zn1—N3	109.08 (17)	C6—N2—Zn1	117.7 (3)
N5—Zn1—N1	105.95 (16)	C8—N2—Zn1	119.2 (5)
N3—Zn1—N1	141.17 (14)	C10—N3—C9	125.9 (9)
N5—Zn1—N2	110.56 (19)	C10—N3—Zn1	118.0 (3)
N3—Zn1—N2	75.37 (15)	C9—N3—Zn1	115.9 (8)
N1—Zn1—N2	77.12 (15)	N2—C8—C9	108.5 (11)
N5—Zn1—N4	101.91 (17)	N2—C8—H8A	110.0
N3—Zn1—N4	77.11 (14)	C9—C8—H8A	110.0
N1—Zn1—N4	111.48 (15)	N2—C8—H8B	110.0
N2—Zn1—N4	142.71 (17)	C9—C8—H8B	110.0
O1—Cl1—O2	110.3 (5)	H8A—C8—H8B	108.4
O1—Cl1—O4	108.8 (4)	N3—C9—C8	108.2 (9)
O2—Cl1—O4	108.0 (3)	N3—C9—H9A	110.1
O1—Cl1—O3	109.7 (3)	C8—C9—H9A	110.1
O2—Cl1—O3	110.0 (3)	N3—C9—H9B	110.1
O4—Cl1—O3	110.1 (3)	C8—C9—H9B	110.1
C1—N1—C5	118.6 (4)	H9A—C9—H9B	108.4
C1—N1—Zn1	127.1 (3)	C9'—C8'—H8'A	111.3
C5—N1—Zn1	114.2 (3)	C9'—C8'—H8'B	111.3
C16—N4—C12	118.9 (4)	H8'A—C8'—H8'B	109.2
C16—N4—Zn1	127.5 (4)	C8'—C9'—H9'A	110.2
C12—N4—Zn1	113.3 (3)	C8'—C9'—H9'B	110.2
C17—N5—Zn1	166.6 (5)	H9'A—C9'—H9'B	108.5
N1—C1—C2	122.5 (5)	N3—C10—C12	114.9 (4)
N1—C1—H1	118.7	N3—C10—C11	125.6 (5)
C2—C1—H1	118.7	C12—C10—C11	119.4 (4)
C3—C2—C1	119.1 (5)	C10—C11—H11A	109.5
C3—C2—H2	120.5	C10—C11—H11B	109.5
C1—C2—H2	120.5	H11A—C11—H11B	109.5
C2—C3—C4	119.2 (5)	C10—C11—H11C	109.5
C2—C3—H3	120.4	H11A—C11—H11C	109.5
C4—C3—H3	120.4	H11B—C11—H11C	109.5
C3—C4—C5	119.7 (5)	N4—C12—C13	120.8 (4)
C3—C4—H4	120.1	N4—C12—C10	116.0 (4)
C5—C4—H4	120.1	C13—C12—C10	123.2 (4)
N1—C5—C4	121.0 (5)	C14—C13—C12	119.6 (5)
N1—C5—C6	115.9 (4)	C14—C13—H13	120.2
C4—C5—C6	123.1 (5)	C12—C13—H13	120.2
N2—C6—C7	126.1 (5)	C15—C14—C13	119.4 (5)
N2—C6—C5	114.4 (4)	C15—C14—H14	120.3
C7—C6—C5	119.5 (5)	C13—C14—H14	120.3
C6—C7—H7A	109.5	C14—C15—C16	119.2 (5)
C6—C7—H7B	109.5	C14—C15—H15	120.4
H7A—C7—H7B	109.5	C16—C15—H15	120.4
C6—C7—H7C	109.5	N4—C16—C15	122.0 (5)
H7A—C7—H7C	109.5	N4—C16—H16	119.0
H7B—C7—H7C	109.5	C15—C16—H16	119.0
C6—N2—C8	117.1 (7)	N5—C17—S1	179.2 (5)

Experimental details

Crystal data
Chemical formula	[Zn(NCS)(C₁₆H₁₈N₄)]ClO₄
M_r	489.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.685 (2), 13.963 (3), 17.374 (2)
β (°)	99.690 (3)
V (Å³)	2076.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.45
Crystal size (mm)	0.32 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.655, 0.671
No. of measured, independent and observed [I > 2σ(I)] reflections	16681, 4529, 2534
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.170, 1.02
No. of reflections	4529
No. of parameters	282
No. of restraints	48
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.66

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

Selected geometric parameters (Å, º) top

Zn1—N5	1.982 (5)	Zn1—N2	2.102 (4)
Zn1—N3	2.099 (4)	Zn1—N4	2.115 (4)
Zn1—N1	2.100 (4)

N5—Zn1—N3	109.08 (17)	N1—Zn1—N2	77.12 (15)
N5—Zn1—N1	105.95 (16)	N5—Zn1—N4	101.91 (17)
N3—Zn1—N1	141.17 (14)	N3—Zn1—N4	77.11 (14)
N5—Zn1—N2	110.56 (19)	N1—Zn1—N4	111.48 (15)
N3—Zn1—N2	75.37 (15)	N2—Zn1—N4	142.71 (17)

Acknowledgements

This work was supported financially by Dezhou University, People's Republic of China.

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