Dichloridobis{2-[(1H-1,2,4-triazol-1-yl)meth­yl]-1H-benzimidazole-κN3}­zinc(II)

Zhang, W.-P.; Zhang, J.-L.; Hao, B.-L.; Yang, H.-X.

doi:10.1107/S1600536813008283

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page m241

https://doi.org/10.1107/S1600536813008283

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Dichloridobis{2-[(1H-1,2,4-triazol-1-yl)methyl]-1H-benzimidazole-κN³}zinc(II)

Wei-Peng Zhang,^a Jiao-Lin Zhang,^a Bao-Lian Hao ^a and Huai-Xia Yang ^a ^*

^aPharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China
^*Correspondence e-mail: yanghuaixia886@163.com

(Received 19 March 2013; accepted 26 March 2013; online 5 April 2013)

In the title complex, [ZnCl₂(C₁₀H₉N₅)₂], the Zn^II ion is coordinated by two N atoms from two 2-[(1H-1,2,4-triazol-1-yl)methyl]-1H-benzimidazole (tmb) ligands and by two chloride ligands in a slightly distorted tetrahedral geometry. In the tmb ligands, the benzimidazole rings systems are essentially planar, with maximum deviations from the mean plane of 0.021 (3) and 0.030 (3) Å, and form dihedral angles of 73.2 (2) and 83.5 (2)° with the triazole rings. In the crystal, N—H⋯N hydrogen bonds link complex molecules into chains along [010]. In addition, weak C—H⋯Cl and C—H⋯N hydrogen bonds complete a three-dimensional network. Two weak intramolecular C—H⋯Cl hydrogen bonds are also observed.

Related literature

For background to complexes based on the 2-[(1H-1,2,4-triazol-1-yl)methyl]-1H-benzimidazole (tmb) ligand, see: Jin et al. (2012 ); Wang et al. (2012 ).

Experimental

Crystal data

[ZnCl₂(C₁₀H₉N₅)₂]
M_r = 534.73
Monoclinic, P 2₁ /c
a = 11.571 (2) Å
b = 14.109 (3) Å
c = 16.357 (6) Å
β = 121.03 (2)°
V = 2288.2 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 293 K
0.18 × 0.17 × 0.08 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 ) T_min = 0.795, T_max = 0.901
15780 measured reflections
4234 independent reflections
3396 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.108
S = 1.13
4234 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.29 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
N2—H2B⋯N5ⁱ	0.86	2.04	2.899 (4)	177
N7—H7B⋯N10ⁱⁱ	0.86	1.96	2.814 (4)	172
C3—H3B⋯Cl1	0.97	2.83	3.641 (4)	142
C13—H13B⋯Cl1	0.97	2.73	3.628 (4)	154
C2—H2A⋯Cl1ⁱⁱⁱ	0.93	2.77	3.596 (4)	148
C13—H13A⋯N4^iv	0.97	2.62	3.261 (5)	124
C18—H18A⋯Cl1^v	0.93	2.81	3.635 (4)	149
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; 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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813008283/lh5599sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008283/lh5599Isup2.hkl

checkCIF report

Comment top

In recent years we have focused our attention on the design and synthesis of complexes based on the 2-[(1H-1,2,4-triazol-1-yl)methyl]-1H-benzimidazole (tmb) ligand since it possesses various coordination modes and can act as both a hydrogen bond acceptor and donor due to the amino group of benzimidazole ring and N atoms of benzimidazole and imidazole rings (Jin et al., 2012; Wang et al., 2012). In order to enrich the categories and numbers of complexes with this ligand, we have selected tmb as the ligand to self-assemble with ZnCl₂. The crystal structure of the title complex is reported herein.

As shown in Figure 1, two 2-((1H-1,2,4-triazol-1-yl)methyl)-1H-benzimidazole ligands and two Cl ligands coordinate to the Zn^II ion resulting in a slightly distorted tetrahedral geometry. In the tmb ligands, the benzimidazole rings systems are essentially planar with maximum deviations for an atom of 0.021 (3) for N1 and 0.030 (3) Å for N7. In the tmb ligands, the mean planes of the benzimidazole rings systems form dihedral angles of 73.2 (2) [C4-C10/N1/N2 and C1/C2/N3-N5] and 83.5 (2)° [C14-C20/N6/N7 and C11/C12/N8-N10] with the triazole rings. In the crystal, N—H···N hydrogen bonds link complex molecules into one-dimensional chains along [010]. In addition, weak C—H···Cl and C—H···N hydrogen bonds complete a three-dimensional network. Two weak intramolecular C—H···Cl hydrogen bonds are also observed.

Related literature top

For background to complexes based on the 2-[(1H-1,2,4-triazol-1-yl)methyl]-1H-benzimidazole (tmb) ligand, see: Jin et al. (2012); Wang et al. (2012).

Experimental top

A mixture of ZnCl₂ (0.1 mmol), 2-[(1H-1,2,4-triazol-1-yl)methyl]-1H-benzimidazole (tmb; 0.1 mmol), and water (10 ml) was placed in a 25 ml Teflon-lined stainless steel vessel and heated at 373 K for 72 h, then cooled to room temperature. Colourless crystals were obtained from the filtrate and dried in air.

Structure description top

For background to complexes based on the 2-[(1H-1,2,4-triazol-1-yl)methyl]-1H-benzimidazole (tmb) ligand, see: Jin et al. (2012); Wang et al. (2012).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 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: publCIF (Westrip, 2010).

Figures top

Fig. 1. View of the title complex showing 30% probability displacement ellipsolids.

Dichloridobis{2-[(1H-1,2,4-triazol-1-yl)methyl]-1H-benzimidazole-κN³}zinc(II) top

Crystal data top

[ZnCl₂(C₁₀H₉N₅)₂]	F(000) = 1088
M_r = 534.73	D_x = 1.552 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.571 (2) Å	Cell parameters from 4370 reflections
b = 14.109 (3) Å	θ = 2.1–27.9°
c = 16.357 (6) Å	µ = 1.34 mm⁻¹
β = 121.03 (2)°	T = 293 K
V = 2288.2 (10) Å³	Prism, colourless
Z = 4	0.18 × 0.17 × 0.08 mm

Data collection top

Rigaku Saturn diffractometer	4234 independent reflections
Radiation source: fine-focus sealed tube	3396 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.5°, θ_min = 2.1°
ω scans	h = −14→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC Inc., 2004)	k = −16→17
T_min = 0.795, T_max = 0.901	l = −19→19
15780 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0318P)² + 1.7955P] where P = (F_o² + 2F_c²)/3
4234 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[ZnCl₂(C₁₀H₉N₅)₂]	V = 2288.2 (10) Å³
M_r = 534.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.571 (2) Å	µ = 1.34 mm⁻¹
b = 14.109 (3) Å	T = 293 K
c = 16.357 (6) Å	0.18 × 0.17 × 0.08 mm
β = 121.03 (2)°

Data collection top

Rigaku Saturn diffractometer	4234 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC Inc., 2004)	3396 reflections with I > 2σ(I)
T_min = 0.795, T_max = 0.901	R_int = 0.054
15780 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.13	Δρ_max = 0.29 e Å⁻³
4234 reflections	Δρ_min = −0.37 e Å⁻³
298 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	0.68322 (4)	0.25039 (3)	0.24838 (3)	0.03071 (14)
Cl1	0.45848 (10)	0.23530 (8)	0.15278 (7)	0.0509 (3)
Cl2	0.78345 (11)	0.26118 (8)	0.16349 (8)	0.0497 (3)
N1	0.7393 (3)	0.1337 (2)	0.3354 (2)	0.0292 (7)
N2	0.7295 (3)	0.0240 (2)	0.4293 (2)	0.0355 (8)
H2B	0.7070	−0.0035	0.4660	0.043*
N3	0.4890 (3)	0.1159 (2)	0.4056 (2)	0.0296 (7)
N4	0.4098 (3)	0.0541 (2)	0.3346 (2)	0.0397 (8)
N5	0.3487 (3)	0.0612 (2)	0.4450 (2)	0.0408 (8)
N6	0.7382 (3)	0.3573 (2)	0.3450 (2)	0.0296 (7)
N7	0.7435 (3)	0.4386 (2)	0.4625 (2)	0.0364 (8)
H7B	0.7163	0.4726	0.4931	0.044*
N8	0.4444 (3)	0.4297 (2)	0.3544 (2)	0.0365 (8)
N9	0.4108 (4)	0.3434 (3)	0.3729 (3)	0.0538 (10)
N10	0.3299 (3)	0.4606 (3)	0.4226 (2)	0.0451 (9)
C1	0.3285 (4)	0.0233 (3)	0.3628 (3)	0.0430 (10)
H1A	0.2617	−0.0214	0.3284	0.052*
C2	0.4508 (4)	0.1196 (3)	0.4693 (3)	0.0365 (9)
H2A	0.4902	0.1579	0.5234	0.044*
C3	0.5917 (4)	0.1708 (3)	0.4012 (3)	0.0343 (9)
H3A	0.6427	0.2069	0.4596	0.041*
H3B	0.5485	0.2153	0.3486	0.041*
C4	0.6863 (4)	0.1093 (3)	0.3879 (3)	0.0303 (8)
C5	0.8245 (4)	0.0578 (2)	0.3448 (3)	0.0298 (8)
C6	0.9044 (4)	0.0445 (3)	0.3054 (3)	0.0394 (10)
H6A	0.9119	0.0906	0.2677	0.047*
C7	0.9728 (4)	−0.0410 (3)	0.3253 (3)	0.0488 (11)
H7A	1.0272	−0.0526	0.2999	0.059*
C8	0.9624 (4)	−0.1100 (3)	0.3820 (3)	0.0532 (12)
H8A	1.0091	−0.1667	0.3930	0.064*
C9	0.8851 (4)	−0.0962 (3)	0.4218 (3)	0.0474 (11)
H9A	0.8789	−0.1419	0.4603	0.057*
C10	0.8166 (4)	−0.0113 (3)	0.4024 (3)	0.0332 (9)
C11	0.3423 (5)	0.3666 (3)	0.4131 (4)	0.0575 (13)
H11A	0.3046	0.3214	0.4339	0.069*
C12	0.3953 (4)	0.4976 (3)	0.3841 (3)	0.0391 (10)
H12A	0.4055	0.5622	0.3784	0.047*
C13	0.5230 (4)	0.4372 (3)	0.3080 (3)	0.0402 (10)
H13A	0.5202	0.5021	0.2876	0.048*
H13B	0.4825	0.3973	0.2516	0.048*
C14	0.6671 (4)	0.4081 (2)	0.3725 (3)	0.0312 (8)
C15	0.8726 (4)	0.4064 (3)	0.4977 (3)	0.0357 (9)
C16	0.9907 (4)	0.4177 (3)	0.5860 (3)	0.0474 (11)
H16A	0.9913	0.4492	0.6362	0.057*
C17	1.1066 (4)	0.3798 (3)	0.5951 (3)	0.0501 (11)
H17A	1.1878	0.3864	0.6526	0.060*
C18	1.1045 (4)	0.3318 (3)	0.5199 (3)	0.0453 (10)
H18A	1.1848	0.3076	0.5284	0.054*
C19	0.9880 (4)	0.3192 (3)	0.4339 (3)	0.0394 (10)
H19A	0.9879	0.2866	0.3845	0.047*
C20	0.8700 (4)	0.3568 (2)	0.4231 (3)	0.0303 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0327 (3)	0.0346 (2)	0.0271 (2)	−0.0017 (2)	0.01704 (19)	0.0012 (2)
Cl1	0.0329 (6)	0.0760 (8)	0.0360 (6)	−0.0080 (5)	0.0122 (5)	0.0010 (5)
Cl2	0.0603 (7)	0.0596 (7)	0.0490 (6)	0.0071 (6)	0.0422 (6)	0.0101 (5)
N1	0.0346 (18)	0.0314 (16)	0.0269 (16)	−0.0019 (14)	0.0196 (15)	0.0015 (13)
N2	0.042 (2)	0.0355 (18)	0.0383 (19)	0.0013 (15)	0.0270 (17)	0.0085 (15)
N3	0.0360 (18)	0.0282 (16)	0.0311 (17)	0.0003 (14)	0.0219 (15)	0.0011 (13)
N4	0.046 (2)	0.043 (2)	0.0349 (19)	−0.0053 (16)	0.0247 (17)	−0.0046 (16)
N5	0.046 (2)	0.042 (2)	0.048 (2)	0.0040 (17)	0.0343 (18)	0.0073 (17)
N6	0.0311 (17)	0.0321 (17)	0.0295 (17)	0.0040 (13)	0.0182 (15)	0.0021 (14)
N7	0.043 (2)	0.0366 (18)	0.0391 (19)	0.0059 (15)	0.0285 (17)	−0.0036 (15)
N8	0.0377 (19)	0.043 (2)	0.0364 (19)	0.0090 (15)	0.0249 (16)	0.0064 (15)
N9	0.068 (3)	0.046 (2)	0.073 (3)	0.0085 (19)	0.054 (2)	0.008 (2)
N10	0.040 (2)	0.062 (2)	0.040 (2)	0.0096 (18)	0.0247 (18)	0.0006 (18)
C1	0.041 (2)	0.042 (2)	0.046 (3)	−0.006 (2)	0.023 (2)	0.002 (2)
C2	0.048 (3)	0.037 (2)	0.036 (2)	0.0027 (19)	0.029 (2)	0.0005 (18)
C3	0.041 (2)	0.031 (2)	0.041 (2)	−0.0027 (17)	0.028 (2)	0.0004 (17)
C4	0.031 (2)	0.031 (2)	0.028 (2)	−0.0020 (16)	0.0151 (17)	−0.0018 (16)
C5	0.026 (2)	0.030 (2)	0.031 (2)	0.0007 (16)	0.0129 (17)	−0.0004 (16)
C6	0.037 (2)	0.046 (2)	0.041 (2)	0.0018 (19)	0.024 (2)	0.0052 (19)
C7	0.042 (3)	0.057 (3)	0.055 (3)	0.007 (2)	0.030 (2)	−0.001 (2)
C8	0.047 (3)	0.043 (3)	0.068 (3)	0.016 (2)	0.029 (3)	0.004 (2)
C9	0.047 (3)	0.036 (2)	0.064 (3)	0.010 (2)	0.032 (2)	0.012 (2)
C10	0.030 (2)	0.036 (2)	0.036 (2)	−0.0032 (17)	0.0180 (18)	0.0007 (17)
C11	0.064 (3)	0.057 (3)	0.075 (4)	0.006 (2)	0.052 (3)	0.011 (3)
C12	0.039 (2)	0.041 (2)	0.036 (2)	0.0101 (19)	0.018 (2)	0.0000 (18)
C13	0.042 (2)	0.052 (3)	0.035 (2)	0.014 (2)	0.025 (2)	0.0104 (19)
C14	0.036 (2)	0.030 (2)	0.034 (2)	0.0039 (17)	0.0231 (19)	0.0039 (17)
C15	0.037 (2)	0.034 (2)	0.039 (2)	−0.0007 (17)	0.0214 (19)	−0.0002 (18)
C16	0.048 (3)	0.057 (3)	0.036 (2)	−0.008 (2)	0.021 (2)	−0.007 (2)
C17	0.039 (3)	0.051 (3)	0.044 (3)	−0.009 (2)	0.010 (2)	0.001 (2)
C18	0.031 (2)	0.044 (2)	0.054 (3)	0.0043 (19)	0.017 (2)	0.003 (2)
C19	0.037 (2)	0.032 (2)	0.049 (3)	0.0040 (18)	0.023 (2)	−0.0036 (19)
C20	0.033 (2)	0.0229 (18)	0.035 (2)	−0.0013 (15)	0.0177 (18)	−0.0009 (16)

Geometric parameters (Å, º) top

Zn1—N6	2.035 (3)	C3—C4	1.498 (5)
Zn1—N1	2.051 (3)	C3—H3A	0.9700
Zn1—Cl2	2.2264 (11)	C3—H3B	0.9700
Zn1—Cl1	2.2496 (13)	C5—C6	1.385 (5)
N1—C4	1.332 (4)	C5—C10	1.392 (5)
N1—C5	1.410 (4)	C6—C7	1.386 (5)
N2—C4	1.344 (4)	C6—H6A	0.9300
N2—C10	1.384 (4)	C7—C8	1.393 (6)
N2—H2B	0.8601	C7—H7A	0.9300
N3—C2	1.326 (4)	C8—C9	1.364 (6)
N3—N4	1.361 (4)	C8—H8A	0.9300
N3—C3	1.451 (4)	C9—C10	1.379 (5)
N4—C1	1.315 (5)	C9—H9A	0.9300
N5—C2	1.323 (5)	C11—H11A	0.9300
N5—C1	1.352 (5)	C12—H12A	0.9300
N6—C14	1.333 (4)	C13—C14	1.500 (5)
N6—C20	1.396 (5)	C13—H13A	0.9700
N7—C14	1.339 (5)	C13—H13B	0.9700
N7—C15	1.372 (5)	C15—C16	1.394 (6)
N7—H7B	0.8600	C15—C20	1.394 (5)
N8—C12	1.327 (5)	C16—C17	1.379 (6)
N8—N9	1.358 (4)	C16—H16A	0.9300
N8—C13	1.458 (4)	C17—C18	1.394 (6)
N9—C11	1.306 (5)	C17—H17A	0.9300
N10—C12	1.317 (5)	C18—C19	1.368 (6)
N10—C11	1.351 (5)	C18—H18A	0.9300
C1—H1A	0.9300	C19—C20	1.389 (5)
C2—H2A	0.9300	C19—H19A	0.9300

N6—Zn1—N1	101.28 (12)	C5—C6—H6A	121.8
N6—Zn1—Cl2	112.27 (9)	C7—C6—H6A	121.8
N1—Zn1—Cl2	114.06 (9)	C6—C7—C8	122.0 (4)
N6—Zn1—Cl1	113.37 (9)	C6—C7—H7A	119.0
N1—Zn1—Cl1	104.20 (9)	C8—C7—H7A	119.0
Cl2—Zn1—Cl1	111.11 (5)	C9—C8—C7	121.4 (4)
C4—N1—C5	105.2 (3)	C9—C8—H8A	119.3
C4—N1—Zn1	124.7 (2)	C7—C8—H8A	119.3
C5—N1—Zn1	129.7 (2)	C8—C9—C10	117.1 (4)
C4—N2—C10	107.7 (3)	C8—C9—H9A	121.5
C4—N2—H2B	126.1	C10—C9—H9A	121.5
C10—N2—H2B	126.2	C9—C10—N2	131.8 (4)
C2—N3—N4	110.2 (3)	C9—C10—C5	122.2 (4)
C2—N3—C3	129.2 (3)	N2—C10—C5	106.0 (3)
N4—N3—C3	120.5 (3)	N9—C11—N10	115.5 (4)
C1—N4—N3	101.6 (3)	N9—C11—H11A	122.2
C2—N5—C1	102.3 (3)	N10—C11—H11A	122.2
C14—N6—C20	105.5 (3)	N10—C12—N8	110.4 (4)
C14—N6—Zn1	131.3 (3)	N10—C12—H12A	124.8
C20—N6—Zn1	117.6 (2)	N8—C12—H12A	124.8
C14—N7—C15	108.3 (3)	N8—C13—C14	112.3 (3)
C14—N7—H7B	125.9	N8—C13—H13A	109.1
C15—N7—H7B	125.8	C14—C13—H13A	109.1
C12—N8—N9	109.9 (3)	N8—C13—H13B	109.1
C12—N8—C13	129.6 (3)	C14—C13—H13B	109.1
N9—N8—C13	120.5 (3)	H13A—C13—H13B	107.9
C11—N9—N8	101.9 (3)	N6—C14—N7	111.8 (3)
C12—N10—C11	102.3 (3)	N6—C14—C13	124.4 (3)
N4—C1—N5	115.5 (4)	N7—C14—C13	123.4 (3)
N4—C1—H1A	122.2	N7—C15—C16	132.1 (4)
N5—C1—H1A	122.2	N7—C15—C20	105.7 (3)
N5—C2—N3	110.3 (3)	C16—C15—C20	122.1 (4)
N5—C2—H2A	124.8	C17—C16—C15	116.6 (4)
N3—C2—H2A	124.8	C17—C16—H16A	121.7
N3—C3—C4	112.1 (3)	C15—C16—H16A	121.7
N3—C3—H3A	109.2	C16—C17—C18	121.3 (4)
C4—C3—H3A	109.2	C16—C17—H17A	119.3
N3—C3—H3B	109.2	C18—C17—H17A	119.3
C4—C3—H3B	109.2	C19—C18—C17	122.0 (4)
H3A—C3—H3B	107.9	C19—C18—H18A	119.0
N1—C4—N2	112.5 (3)	C17—C18—H18A	119.0
N1—C4—C3	123.9 (3)	C18—C19—C20	117.7 (4)
N2—C4—C3	123.7 (3)	C18—C19—H19A	121.2
C6—C5—C10	120.9 (3)	C20—C19—H19A	121.2
C6—C5—N1	130.5 (3)	C19—C20—C15	120.3 (4)
C10—C5—N1	108.6 (3)	C19—C20—N6	131.1 (3)
C5—C6—C7	116.5 (4)	C15—C20—N6	108.6 (3)

N6—Zn1—N1—C4	63.8 (3)	C8—C9—C10—N2	178.7 (4)
Cl2—Zn1—N1—C4	−175.4 (3)	C8—C9—C10—C5	0.2 (6)
Cl1—Zn1—N1—C4	−54.1 (3)	C4—N2—C10—C9	−177.6 (4)
N6—Zn1—N1—C5	−125.0 (3)	C4—N2—C10—C5	1.1 (4)
Cl2—Zn1—N1—C5	−4.2 (3)	C6—C5—C10—C9	−1.2 (6)
Cl1—Zn1—N1—C5	117.1 (3)	N1—C5—C10—C9	177.5 (4)
C2—N3—N4—C1	−0.9 (4)	C6—C5—C10—N2	180.0 (3)
C3—N3—N4—C1	−177.1 (3)	N1—C5—C10—N2	−1.4 (4)
N1—Zn1—N6—C14	−97.6 (3)	N8—N9—C11—N10	−0.4 (6)
Cl2—Zn1—N6—C14	140.3 (3)	C12—N10—C11—N9	0.6 (6)
Cl1—Zn1—N6—C14	13.4 (3)	C11—N10—C12—N8	−0.5 (5)
N1—Zn1—N6—C20	51.9 (3)	N9—N8—C12—N10	0.3 (5)
Cl2—Zn1—N6—C20	−70.1 (3)	C13—N8—C12—N10	−179.9 (4)
Cl1—Zn1—N6—C20	163.0 (2)	C12—N8—C13—C14	108.7 (4)
C12—N8—N9—C11	0.0 (5)	N9—N8—C13—C14	−71.5 (5)
C13—N8—N9—C11	−179.8 (4)	C20—N6—C14—N7	−0.9 (4)
N3—N4—C1—N5	0.7 (5)	Zn1—N6—C14—N7	151.4 (3)
C2—N5—C1—N4	−0.2 (5)	C20—N6—C14—C13	172.7 (3)
C1—N5—C2—N3	−0.4 (4)	Zn1—N6—C14—C13	−35.1 (5)
N4—N3—C2—N5	0.9 (4)	C15—N7—C14—N6	−0.3 (4)
C3—N3—C2—N5	176.7 (3)	C15—N7—C14—C13	−174.0 (3)
C2—N3—C3—C4	130.2 (4)	N8—C13—C14—N6	139.7 (4)
N4—N3—C3—C4	−54.4 (4)	N8—C13—C14—N7	−47.5 (5)
C5—N1—C4—N2	−0.5 (4)	C14—N7—C15—C16	179.6 (4)
Zn1—N1—C4—N2	172.5 (2)	C14—N7—C15—C20	1.4 (4)
C5—N1—C4—C3	178.2 (3)	N7—C15—C16—C17	−176.0 (4)
Zn1—N1—C4—C3	−8.8 (5)	C20—C15—C16—C17	2.0 (6)
C10—N2—C4—N1	−0.4 (4)	C15—C16—C17—C18	−0.7 (6)
C10—N2—C4—C3	−179.1 (3)	C16—C17—C18—C19	−0.5 (7)
N3—C3—C4—N1	143.9 (3)	C17—C18—C19—C20	0.5 (6)
N3—C3—C4—N2	−37.6 (5)	C18—C19—C20—C15	0.7 (6)
C4—N1—C5—C6	179.6 (4)	C18—C19—C20—N6	178.6 (4)
Zn1—N1—C5—C6	7.1 (6)	N7—C15—C20—C19	176.4 (3)
C4—N1—C5—C10	1.2 (4)	C16—C15—C20—C19	−2.1 (6)
Zn1—N1—C5—C10	−171.4 (2)	N7—C15—C20—N6	−1.9 (4)
C10—C5—C6—C7	1.1 (6)	C16—C15—C20—N6	179.7 (3)
N1—C5—C6—C7	−177.2 (4)	C14—N6—C20—C19	−176.3 (4)
C5—C6—C7—C8	−0.2 (6)	Zn1—N6—C20—C19	26.9 (5)
C6—C7—C8—C9	−0.7 (7)	C14—N6—C20—C15	1.7 (4)
C7—C8—C9—C10	0.7 (7)	Zn1—N6—C20—C15	−155.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N5ⁱ	0.86	2.04	2.899 (4)	177
N7—H7B···N10ⁱⁱ	0.86	1.96	2.814 (4)	172
C3—H3B···Cl1	0.97	2.83	3.641 (4)	142
C13—H13B···Cl1	0.97	2.73	3.628 (4)	154
C2—H2A···Cl1ⁱⁱⁱ	0.93	2.77	3.596 (4)	148
C13—H13A···N4^iv	0.97	2.62	3.261 (5)	124
C18—H18A···Cl1^v	0.93	2.81	3.635 (4)	149

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

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₀H₉N₅)₂]
M_r	534.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.571 (2), 14.109 (3), 16.357 (6)
β (°)	121.03 (2)
V (Å³)	2288.2 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.34
Crystal size (mm)	0.18 × 0.17 × 0.08

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC Inc., 2004)
T_min, T_max	0.795, 0.901
No. of measured, independent and observed [I > 2σ(I)] reflections	15780, 4234, 3396
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.108, 1.13
No. of reflections	4234
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.37

Computer programs: CrystalClear (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N5ⁱ	0.86	2.04	2.899 (4)	176.6
N7—H7B···N10ⁱⁱ	0.86	1.96	2.814 (4)	172.4
C3—H3B···Cl1	0.97	2.83	3.641 (4)	142.1
C13—H13B···Cl1	0.97	2.73	3.628 (4)	154.2
C2—H2A···Cl1ⁱⁱⁱ	0.93	2.77	3.596 (4)	148.0
C13—H13A···N4^iv	0.97	2.62	3.261 (5)	123.9
C18—H18A···Cl1^v	0.93	2.81	3.635 (4)	148.6

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

Acknowledgements

The study was supported by the Science and Technology Department of Henan Province (grant No. 082102330003).

References

Jin, G.-H., Yang, Y., Zhou, X.-L. & Meng, X.-R. (2012). Z. Naturforsch. Teil B, 67, 29–35. CSD CrossRef CAS Google Scholar
Rigaku/MSC (2004). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, X.-X., Han, X., Qiao, Z., Jin, G.-H. & Meng, X.-R. (2012). Z. Naturforsch. Teil B, 67, 783–790. Web of Science CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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