Bis[4-(4-methoxy­phen­yl)-4H-1,2,4-triazole-κN1]bis­(thio­cyanato-κN)zinc(II)

Zuo, Y.

doi:10.1107/S1600536808008325

metal-organic compounds

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Volume 64| Part 5| May 2008| Page m609

doi:10.1107/S1600536808008325

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Bis[4-(4-methoxyphenyl)-4H-1,2,4-triazole-κN¹]bis(thiocyanato-κN)zinc(II)

Ya Zuo ^a ^*

^aCollege of Science, Inner Mongolia Agricultural University, Inner Mongolia 010018, People's Republic of China
^*Correspondence e-mail: yazoe@mail.nankai.edu.cn

(Received 5 March 2008; accepted 27 March 2008; online 2 April 2008)

In the title complex, [Zn(NCS)₂(C₉H₉N₃O)₂], the Zn^II ion is coordinated by two N atoms from the NCS⁻ anions and two N atoms from two 4-(4-methoxyphenyl)-4H-1,2,4-triazole ligands in a slightly distorted tetrahedral geometry. Three intermolecular weak hydrogen-bonding contacts of the types C—H⋯N, C—H⋯S and C—H⋯O are observed in the crystal structure.

Related literature

For related literature, see: Han et al. (2006 ); Ling & Zhang (2007 ); Thomann et al. (1994 ); Yin et al. (2007 ); Zhao et al. (2002 ); Zhou et al. (2007 ).

Experimental

Crystal data

[Zn(NCS)₂(C₉H₉N₃O)₂]
M_r = 531.91
Monoclinic, P 2₁ /n
a = 7.812 (3) Å
b = 17.111 (6) Å
c = 18.201 (6) Å
β = 99.726 (6)°
V = 2398.0 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 293 (2) K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.700, T_max = 0.884
13731 measured reflections
4932 independent reflections
2127 reflections with I > 2σ(I)
R_int = 0.121

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.158
S = 0.97
4932 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N8	1.923 (6)
Zn1—N7	1.970 (6)
Zn1—N1	2.005 (5)
Zn1—N4	2.009 (5)

N8—Zn1—N7	112.9 (2)
N8—Zn1—N1	112.1 (2)
N7—Zn1—N1	108.5 (2)
N8—Zn1—N4	116.4 (2)
N7—Zn1—N4	103.8 (2)
N1—Zn1—N4	102.2 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N5ⁱ	0.93	2.51	3.438 (8)	177
C7—H7⋯S1ⁱⁱ	0.93	2.86	3.735 (6)	158
C10—H10⋯O1ⁱⁱⁱ	0.93	2.42	3.265 (8)	151
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x, -y+2, -z; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); 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: 10.1107/S1600536808008325/si2077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008325/si2077Isup2.hkl

checkCIF report

Comment top

The organic ligands, 1,2,4-triazole and its derivatives continue to attract considerable attention due to the luminescent, magnetic, and electronic properties of their complexes and the potential application in material science (Yin et al., 2007; Zhou, et al., 2007; Han et al., 2006). On the other hand, 1,2,4-triazole and its derivatives combine the coordination geometry of both pyrazole and imidazole with regard to the arrangement and coordination of their three heteroatoms. Compared with the chelating to the metal centers with the nitrogen atom in the 1,2-positions (Thomann et al., 1994), it is familiar that the nitrogen atom serve as the solo coordinated atom (Ling & Zhang, 2007). In order to explore furthur the coordination chemistry of the 4-(4-methoxyphenyl)-4H-1,2,4-triazole system (hereafter abbreviated as L), the title complex was synthesized.

The coordination geometry of the Zn^II ion is a slightly distorted tetrahedron, in which each Zn^II ion is coordinated to two nitrogen atoms from the NCS^- anions and two nitrogen atoms from two ligands L. (Fig. 1). The separations of Zn—N range from 1.923 (6) to 2.009 (5)Å (Table 1), which is close to the corresponding distances in the 4-coordinated Zn compound (2.050 (4)Å and 2.023 (4) Å) reported previously (Han et al., 2006), while the average distance of Zn—N is 2.162 (2)Å in the 6-coordinated (Ling & Zhang, 2007) and 2.065 (2)Å in the 5-coordinated (Yin et al., 2007) compounds, respectively. The bond angles around Zn^II ions vary between 102.2 (2)° and 116.4 (2)°. The central Zn^II ion, is coordinated with the L ligands in the 1-position, which is the common coordination mode (Ling & Zhang, 2007) of 1,2,4-Triazole and its derivatives, differently from that in the 1,2-position (Thomann et al., 1994). As the important structural parameters, the dihedral angles between the triazole and phenyl rings of the two L ligands are distinct, that of C1—N3—C3—C8 is equal to 39.2 (9)°, while the value of C10—N6—C12—C17 is 93.8 (8)°. With regard to the two trans thiocyanato NCS^- anions, the group is almost linear with an N7—C19—S1 angle of 178.8 (8)° and N8—C20—S2 angle of 178.1 (7)°. The connection between Zn atoms and NCS groups are bent with a C20—N8—Zn1 angle of 168.1 (6)°, and a C19—N7—Zn1 angle of 160.9 (6)° (Zhao et al., 2002). Three intermoleular hydrogen bonding contacts of the type C—H···N, C—H···S and C—H···O are observed in the title structure (Table 2).

Related literature top

For related literature, see: Han et al. (2006); Ling & Zhang (2007); Thomann et al. (1994); Yin et al. (2007); Zhao et al. (2002); Zhou et al. (2007).

Experimental top

The compound was synthesized under hydrothermal conditions. A mixture of L (L=4-(1,2,4-triazol)-1-methoxy-benzene) (0.3 mmol, 0.045 g), ZnSO₄˙7H₂O (0.1 mmol, 0.029 g), KSCN (0.2 mmol, 0.019 g) and water (10 mL) was placed in a 25 mL acid digestion bomb and heated at 160° for two days, then equably cooled to room temperature for three days. After washed by 5 ml water for twice, colorless block crystals of the title compound were obtained.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 ORTEP plot of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering schemes. H atoms have been omitted for clarity.

Bis[4-(4-methoxyphenyl)-4H-1,2,4-triazole-κN¹]bis(thiocyanato-κN)zinc(II) top

Crystal data top

[Zn(NCS)₂(C₉H₉N₃O)₂]	F(000) = 1088
M_r = 531.91	D_x = 1.473 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.812 (3) Å	Cell parameters from 713 reflections
b = 17.111 (6) Å	θ = 2.6–21.1°
c = 18.201 (6) Å	µ = 1.23 mm⁻¹
β = 99.726 (6)°	T = 293 K
V = 2398.0 (15) Å³	Block, colorless
Z = 4	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4932 independent reflections
Radiation source: fine-focus sealed tube	2127 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.121
ϕ and O scans	θ_max = 26.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.700, T_max = 0.884	k = −21→14
13731 measured reflections	l = −22→18

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0555P)²] where P = (F_o² + 2F_c²)/3
4932 reflections	(Δ/σ)_max = 0.001
300 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Zn(NCS)₂(C₉H₉N₃O)₂]	V = 2398.0 (15) Å³
M_r = 531.91	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.812 (3) Å	µ = 1.23 mm⁻¹
b = 17.111 (6) Å	T = 293 K
c = 18.201 (6) Å	0.16 × 0.12 × 0.10 mm
β = 99.726 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4932 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2127 reflections with I > 2σ(I)
T_min = 0.700, T_max = 0.884	R_int = 0.121
13731 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 0.97	Δρ_max = 0.39 e Å⁻³
4932 reflections	Δρ_min = −0.33 e Å⁻³
300 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
Zn1	0.36832 (9)	1.10583 (5)	0.05909 (4)	0.0434 (3)
N1	0.2576 (6)	1.0131 (3)	0.0996 (3)	0.0448 (14)
N2	0.2447 (7)	1.0191 (4)	0.1742 (3)	0.0506 (15)
N3	0.1960 (6)	0.8971 (4)	0.1360 (3)	0.0417 (13)
O1	0.0331 (6)	0.5821 (3)	0.1525 (2)	0.0495 (12)
C1	0.2292 (7)	0.9405 (4)	0.0785 (3)	0.0393 (16)
H1	0.2317	0.9216	0.0307	0.047*
C2	0.2083 (9)	0.9483 (5)	0.1939 (4)	0.055 (2)
H2	0.1927	0.9346	0.2418	0.066*
C3	0.1559 (8)	0.8147 (4)	0.1374 (3)	0.0364 (15)
C4	0.2212 (8)	0.7714 (4)	0.1995 (3)	0.0436 (17)
H4	0.2949	0.7943	0.2391	0.052*
C5	0.1762 (8)	0.6938 (4)	0.2023 (3)	0.0429 (17)
H5	0.2179	0.6646	0.2447	0.051*
C6	0.0701 (8)	0.6587 (4)	0.1433 (3)	0.0383 (16)
C7	0.0088 (8)	0.7023 (4)	0.0807 (3)	0.0462 (18)
H7	−0.0610	0.6791	0.0400	0.055*
C8	0.0506 (8)	0.7795 (4)	0.0784 (3)	0.0467 (18)
H8	0.0073	0.8089	0.0364	0.056*
C9	−0.0628 (8)	0.5413 (4)	0.0903 (4)	0.060 (2)
H9A	−0.1752	0.5649	0.0767	0.090*
H9B	−0.0762	0.4876	0.1035	0.090*
H9C	−0.0014	0.5440	0.0489	0.090*
N4	0.6037 (6)	1.1085 (3)	0.1237 (3)	0.0423 (13)
N5	0.7566 (7)	1.1233 (4)	0.0996 (3)	0.0586 (18)
N6	0.8049 (6)	1.1152 (3)	0.2222 (3)	0.0421 (14)
O2	1.1582 (6)	1.1055 (3)	0.5135 (2)	0.0655 (14)
C10	0.6367 (8)	1.1026 (4)	0.1966 (3)	0.0464 (16)
H10	0.5541	1.0912	0.2264	0.056*
C11	0.8730 (9)	1.1266 (5)	0.1594 (4)	0.065 (2)
H11	0.9902	1.1359	0.1592	0.078*
C12	0.8924 (7)	1.1139 (4)	0.2991 (3)	0.0385 (15)
C13	0.8962 (8)	1.1802 (4)	0.3406 (3)	0.0474 (18)
H13	0.8410	1.2253	0.3202	0.057*
C14	0.9835 (8)	1.1797 (4)	0.4138 (4)	0.0509 (18)
H14	0.9860	1.2246	0.4429	0.061*
C15	1.0660 (7)	1.1130 (4)	0.4433 (3)	0.0436 (16)
C16	1.0579 (8)	1.0461 (4)	0.4010 (4)	0.0505 (18)
H16	1.1114	1.0007	0.4214	0.061*
C17	0.9708 (8)	1.0461 (4)	0.3285 (4)	0.0462 (18)
H17	0.9651	1.0009	0.2999	0.055*
C18	1.1740 (10)	1.1722 (5)	0.5603 (4)	0.080 (3)
H18A	1.2279	1.2138	0.5372	0.120*
H18B	1.2440	1.1595	0.6074	0.120*
H18C	1.0608	1.1884	0.5681	0.120*
S1	0.1894 (3)	1.35631 (13)	0.11268 (10)	0.0765 (7)
N7	0.2543 (7)	1.2013 (4)	0.0874 (3)	0.0527 (16)
C19	0.2283 (9)	1.2663 (5)	0.0986 (3)	0.0445 (18)
S2	0.3020 (3)	1.10216 (14)	−0.19983 (10)	0.0796 (7)
N8	0.3645 (7)	1.0978 (4)	−0.0466 (3)	0.0619 (17)
C20	0.3357 (8)	1.1003 (4)	−0.1112 (4)	0.0500 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0453 (4)	0.0419 (5)	0.0414 (4)	0.0001 (5)	0.0025 (3)	0.0030 (4)
N1	0.045 (3)	0.045 (4)	0.045 (3)	−0.001 (3)	0.007 (3)	−0.003 (3)
N2	0.070 (4)	0.047 (4)	0.036 (3)	−0.003 (3)	0.012 (3)	−0.007 (3)
N3	0.051 (3)	0.045 (4)	0.029 (3)	−0.001 (3)	0.008 (2)	−0.001 (3)
O1	0.062 (3)	0.040 (3)	0.046 (3)	−0.008 (2)	0.006 (2)	0.001 (2)
C1	0.041 (4)	0.043 (5)	0.033 (4)	0.000 (3)	0.006 (3)	−0.009 (3)
C2	0.073 (5)	0.055 (6)	0.039 (4)	−0.002 (4)	0.013 (4)	−0.005 (4)
C3	0.041 (4)	0.032 (4)	0.037 (4)	0.005 (3)	0.010 (3)	0.000 (3)
C4	0.047 (4)	0.051 (5)	0.031 (4)	−0.007 (4)	0.000 (3)	−0.009 (3)
C5	0.044 (4)	0.048 (5)	0.036 (4)	0.000 (3)	0.004 (3)	0.011 (3)
C6	0.033 (3)	0.043 (5)	0.041 (4)	−0.002 (3)	0.011 (3)	−0.002 (3)
C7	0.052 (4)	0.047 (5)	0.035 (4)	−0.014 (4)	−0.007 (3)	−0.007 (3)
C8	0.059 (4)	0.043 (5)	0.033 (4)	−0.009 (4)	−0.004 (3)	0.012 (3)
C9	0.061 (5)	0.050 (5)	0.068 (5)	−0.010 (4)	0.006 (4)	−0.019 (4)
N4	0.037 (3)	0.052 (4)	0.039 (3)	0.003 (3)	0.007 (2)	0.008 (3)
N5	0.046 (3)	0.087 (5)	0.043 (3)	−0.005 (3)	0.009 (3)	0.009 (3)
N6	0.037 (3)	0.049 (4)	0.039 (3)	−0.003 (3)	0.006 (3)	0.000 (3)
O2	0.071 (3)	0.070 (4)	0.048 (3)	0.003 (3)	−0.012 (2)	−0.011 (3)
C10	0.042 (4)	0.052 (5)	0.045 (4)	−0.002 (4)	0.007 (3)	0.000 (4)
C11	0.045 (4)	0.099 (7)	0.052 (5)	−0.012 (4)	0.012 (4)	0.006 (5)
C12	0.033 (3)	0.046 (5)	0.039 (4)	0.001 (3)	0.009 (3)	−0.003 (4)
C13	0.048 (4)	0.048 (5)	0.046 (4)	0.008 (4)	0.008 (4)	0.008 (4)
C14	0.058 (5)	0.041 (5)	0.053 (4)	0.003 (4)	0.006 (4)	−0.009 (4)
C15	0.039 (3)	0.049 (5)	0.043 (4)	−0.009 (4)	0.006 (3)	−0.006 (4)
C16	0.057 (4)	0.040 (5)	0.050 (4)	0.013 (4)	−0.004 (4)	0.006 (4)
C17	0.045 (4)	0.040 (5)	0.053 (5)	0.009 (4)	0.008 (3)	−0.011 (4)
C18	0.072 (5)	0.100 (8)	0.059 (5)	0.011 (5)	−0.010 (4)	−0.018 (5)
S1	0.128 (2)	0.0453 (13)	0.0492 (12)	0.0171 (13)	−0.0041 (12)	−0.0014 (10)
N7	0.060 (4)	0.050 (4)	0.045 (3)	0.003 (3)	−0.001 (3)	−0.001 (3)
C19	0.053 (4)	0.048 (5)	0.030 (4)	−0.005 (4)	0.000 (3)	0.005 (4)
S2	0.1267 (18)	0.0637 (15)	0.0433 (11)	−0.0087 (14)	−0.0001 (12)	−0.0048 (11)
N8	0.065 (4)	0.070 (5)	0.048 (4)	0.004 (4)	0.003 (3)	0.001 (4)
C20	0.054 (4)	0.038 (4)	0.055 (5)	0.001 (4)	0.001 (4)	−0.001 (4)

Geometric parameters (Å, º) top

Zn1—N8	1.923 (6)	N4—C10	1.312 (7)
Zn1—N7	1.970 (6)	N4—N5	1.365 (6)
Zn1—N1	2.005 (5)	N5—C11	1.296 (7)
Zn1—N4	2.009 (5)	N6—C10	1.336 (7)
N1—C1	1.309 (8)	N6—C11	1.354 (7)
N1—N2	1.382 (7)	N6—C12	1.450 (7)
N2—C2	1.308 (8)	O2—C15	1.363 (7)
N3—C1	1.344 (7)	O2—C18	1.417 (8)
N3—C2	1.361 (8)	C10—H10	0.9300
N3—C3	1.445 (8)	C11—H11	0.9300
O1—C6	1.359 (7)	C12—C13	1.360 (9)
O1—C9	1.430 (7)	C12—C17	1.377 (8)
C1—H1	0.9300	C13—C14	1.391 (8)
C2—H2	0.9300	C13—H13	0.9300
C3—C8	1.375 (8)	C14—C15	1.374 (9)
C3—C4	1.376 (8)	C14—H14	0.9300
C4—C5	1.378 (9)	C15—C16	1.375 (9)
C4—H4	0.9300	C16—C17	1.379 (8)
C5—C6	1.379 (8)	C16—H16	0.9300
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.379 (8)	C18—H18A	0.9600
C7—C8	1.364 (9)	C18—H18B	0.9600
C7—H7	0.9300	C18—H18C	0.9600
C8—H8	0.9300	S1—C19	1.598 (8)
C9—H9A	0.9600	N7—C19	1.155 (8)
C9—H9B	0.9600	S2—C20	1.591 (7)
C9—H9C	0.9600	N8—C20	1.160 (7)

N8—Zn1—N7	112.9 (2)	H9B—C9—H9C	109.5
N8—Zn1—N1	112.1 (2)	C10—N4—N5	107.9 (5)
N7—Zn1—N1	108.5 (2)	C10—N4—Zn1	126.4 (4)
N8—Zn1—N4	116.4 (2)	N5—N4—Zn1	125.5 (4)
N7—Zn1—N4	103.8 (2)	C11—N5—N4	105.4 (5)
N1—Zn1—N4	102.2 (2)	C10—N6—C11	103.4 (5)
C1—N1—N2	108.8 (5)	C10—N6—C12	127.6 (5)
C1—N1—Zn1	134.9 (5)	C11—N6—C12	129.0 (5)
N2—N1—Zn1	114.2 (4)	C15—O2—C18	117.8 (6)
C2—N2—N1	104.9 (5)	N4—C10—N6	110.7 (6)
C1—N3—C2	104.5 (6)	N4—C10—H10	124.6
C1—N3—C3	128.5 (5)	N6—C10—H10	124.6
C2—N3—C3	127.0 (6)	N5—C11—N6	112.6 (6)
C6—O1—C9	117.9 (5)	N5—C11—H11	123.7
N1—C1—N3	109.9 (6)	N6—C11—H11	123.7
N1—C1—H1	125.0	C13—C12—C17	121.3 (6)
N3—C1—H1	125.0	C13—C12—N6	119.1 (6)
N2—C2—N3	111.9 (6)	C17—C12—N6	119.7 (6)
N2—C2—H2	124.0	C12—C13—C14	119.3 (6)
N3—C2—H2	124.0	C12—C13—H13	120.4
C8—C3—C4	119.7 (6)	C14—C13—H13	120.4
C8—C3—N3	121.1 (6)	C15—C14—C13	120.0 (6)
C4—C3—N3	119.2 (6)	C15—C14—H14	120.0
C3—C4—C5	119.2 (6)	C13—C14—H14	120.0
C3—C4—H4	120.4	O2—C15—C14	125.7 (7)
C5—C4—H4	120.4	O2—C15—C16	114.3 (7)
C4—C5—C6	121.0 (6)	C14—C15—C16	120.0 (6)
C4—C5—H5	119.5	C15—C16—C17	120.2 (6)
C6—C5—H5	119.5	C15—C16—H16	119.9
O1—C6—C7	125.0 (6)	C17—C16—H16	119.9
O1—C6—C5	115.9 (6)	C12—C17—C16	119.2 (6)
C7—C6—C5	119.2 (6)	C12—C17—H17	120.4
C8—C7—C6	119.9 (6)	C16—C17—H17	120.4
C8—C7—H7	120.1	O2—C18—H18A	109.5
C6—C7—H7	120.1	O2—C18—H18B	109.5
C7—C8—C3	121.0 (6)	H18A—C18—H18B	109.5
C7—C8—H8	119.5	O2—C18—H18C	109.5
C3—C8—H8	119.5	H18A—C18—H18C	109.5
O1—C9—H9A	109.5	H18B—C18—H18C	109.5
O1—C9—H9B	109.5	C19—N7—Zn1	161.0 (6)
H9A—C9—H9B	109.5	N7—C19—S1	178.8 (7)
O1—C9—H9C	109.5	C20—N8—Zn1	168.1 (6)
H9A—C9—H9C	109.5	N8—C20—S2	178.1 (7)

N8—Zn1—N1—C1	24.0 (7)	N7—Zn1—N4—N5	−108.5 (5)
N7—Zn1—N1—C1	149.4 (6)	N1—Zn1—N4—N5	138.7 (5)
N4—Zn1—N1—C1	−101.4 (6)	C10—N4—N5—C11	−0.9 (8)
N8—Zn1—N1—N2	−175.1 (4)	Zn1—N4—N5—C11	174.2 (5)
N7—Zn1—N1—N2	−49.7 (4)	N5—N4—C10—N6	1.8 (8)
N4—Zn1—N1—N2	59.5 (4)	Zn1—N4—C10—N6	−173.2 (4)
C1—N1—N2—C2	−0.1 (7)	C11—N6—C10—N4	−1.9 (8)
Zn1—N1—N2—C2	−165.9 (4)	C12—N6—C10—N4	−180.0 (6)
N2—N1—C1—N3	0.5 (7)	N4—N5—C11—N6	−0.3 (9)
Zn1—N1—C1—N3	162.2 (4)	C10—N6—C11—N5	1.4 (9)
C2—N3—C1—N1	−0.7 (7)	C12—N6—C11—N5	179.4 (6)
C3—N3—C1—N1	179.2 (5)	C10—N6—C12—C13	−86.6 (8)
N1—N2—C2—N3	−0.4 (7)	C11—N6—C12—C13	95.8 (8)
C1—N3—C2—N2	0.7 (7)	C10—N6—C12—C17	93.7 (8)
C3—N3—C2—N2	−179.3 (6)	C11—N6—C12—C17	−83.8 (9)
C1—N3—C3—C8	−39.2 (9)	C17—C12—C13—C14	1.1 (10)
C2—N3—C3—C8	140.7 (6)	N6—C12—C13—C14	−178.5 (5)
C1—N3—C3—C4	142.3 (6)	C12—C13—C14—C15	0.6 (10)
C2—N3—C3—C4	−37.7 (9)	C18—O2—C15—C14	−1.2 (9)
C8—C3—C4—C5	−1.6 (9)	C18—O2—C15—C16	179.4 (6)
N3—C3—C4—C5	176.9 (5)	C13—C14—C15—O2	178.7 (6)
C3—C4—C5—C6	1.4 (9)	C13—C14—C15—C16	−1.9 (10)
C9—O1—C6—C7	6.3 (9)	O2—C15—C16—C17	−179.0 (6)
C9—O1—C6—C5	−174.3 (5)	C14—C15—C16—C17	1.6 (10)
C4—C5—C6—O1	−179.4 (5)	C13—C12—C17—C16	−1.4 (10)
C4—C5—C6—C7	0.1 (9)	N6—C12—C17—C16	178.2 (5)
O1—C6—C7—C8	178.2 (6)	C15—C16—C17—C12	0.1 (10)
C5—C6—C7—C8	−1.3 (9)	N8—Zn1—N7—C19	−71.6 (17)
C6—C7—C8—C3	1.1 (10)	N1—Zn1—N7—C19	163.5 (16)
C4—C3—C8—C7	0.4 (10)	N4—Zn1—N7—C19	55.3 (17)
N3—C3—C8—C7	−178.0 (6)	Zn1—N7—C19—S1	105 (36)
N8—Zn1—N4—C10	−169.6 (6)	N7—Zn1—N8—C20	−29 (3)
N7—Zn1—N4—C10	65.7 (6)	N1—Zn1—N8—C20	93 (3)
N1—Zn1—N4—C10	−47.1 (6)	N4—Zn1—N8—C20	−149 (3)
N8—Zn1—N4—N5	16.2 (6)	Zn1—N8—C20—S2	180 (100)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N5ⁱ	0.93	2.51	3.438 (8)	177
C7—H7···S1ⁱⁱ	0.93	2.86	3.735 (6)	158
C10—H10···O1ⁱⁱⁱ	0.93	2.42	3.265 (8)	151

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

Experimental details

Crystal data
Chemical formula	[Zn(NCS)₂(C₉H₉N₃O)₂]
M_r	531.91
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.812 (3), 17.111 (6), 18.201 (6)
β (°)	99.726 (6)
V (Å³)	2398.0 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.700, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	13731, 4932, 2127
R_int	0.121
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.158, 0.97
No. of reflections	4932
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.33

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—N8	1.923 (6)	N4—N5	1.365 (6)
Zn1—N7	1.970 (6)	S1—C19	1.598 (8)
Zn1—N1	2.005 (5)	N7—C19	1.155 (8)
Zn1—N4	2.009 (5)	S2—C20	1.591 (7)
N1—N2	1.382 (7)	N8—C20	1.160 (7)

N8—Zn1—N7	112.9 (2)	N7—Zn1—N4	103.8 (2)
N8—Zn1—N1	112.1 (2)	N1—Zn1—N4	102.2 (2)
N7—Zn1—N1	108.5 (2)	N7—C19—S1	178.8 (7)
N8—Zn1—N4	116.4 (2)	N8—C20—S2	178.1 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N5ⁱ	0.93	2.51	3.438 (8)	177.4
C7—H7···S1ⁱⁱ	0.93	2.86	3.735 (6)	157.9
C10—H10···O1ⁱⁱⁱ	0.93	2.42	3.265 (8)	150.9

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

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 64| Part 5| May 2008| Page m609

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