Dichloridobis{1-[(2-methyl-benzimidazol-1-yl-κN(3))meth-yl]benzotriazole}zinc.

The title mononuclear Zn(II) complex, [ZnCl(2)(C(15)H(13)N(5))(2)], is isotypic with the previously reported Hg(II) complex. The Zn(II) atom is located on a twofold rotation axis and has a distorted tetra-hedral environment of two Cl atoms and two N atoms from two heterocyclic ligands. In the crystal, complex mol-ecules are extended by inter-molecular π-π inter-actions [centroid-centroid distance = 3.792 (2) Å] into a three-dimensional supra-molecular network.

Related literature

For background information on complexes constructed from N-heterocyclic ligands, see: Liu et al. (2012 ▶); Bondar et al. (2012 ▶); Shao et al. (2008 ▶); Su et al. (2003 ▶). For the isotypic HgII complex, see: Wu et al. (2009 ▶).

Experimental

Crystal data

[ZnCl2(C15H13N5)2]

M = 662.90

Monoclinic,

a = 15.721 (4) Å

b = 12.617 (4) Å

c = 14.728 (3) Å

β = 99.13 (3)°

V = 2884.3 (13) Å3

Z = 4

Mo Kα radiation

μ = 1.08 mm−1

T = 295 K

0.22 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.797, T max = 0.813

17560 measured reflections

3423 independent reflections

2977 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.137

S = 1.07

3423 reflections

196 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203526X/rk2368sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203526X/rk2368Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[ZnCl2(C15H13N5)2]	F(000) = 1360
Mr = 662.90	Dx = 1.527 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3926 reflections
a = 15.721 (4) Å	θ = 2.1–27.9°
b = 12.617 (4) Å	µ = 1.08 mm−1
c = 14.728 (3) Å	T = 295 K
β = 99.13 (3)°	Needle, colourless
V = 2884.3 (13) Å3	0.22 × 0.20 × 0.20 mm
Z = 4

Rigaku Saturn CCD diffractometer	3423 independent reflections
Radiation source: fine-focus sealed tube	2977 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 28.5714 pixels mm-1	θmax = 27.9°, θmin = 2.4°
ω scans	h = −20→20
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −16→16
Tmin = 0.797, Tmax = 0.813	l = −19→19
17560 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0749P)2 + 0.7625P] where P = (Fo2 + 2Fc2)/3
3423 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq
Zn1	0.0000	0.58999 (3)	0.2500	0.04555 (17)
N1	0.02430 (13)	0.48160 (16)	0.15242 (14)	0.0412 (5)
N2	0.08873 (13)	0.35668 (17)	0.08201 (15)	0.0421 (5)
N3	0.14451 (15)	0.18031 (19)	0.08324 (15)	0.0489 (5)
N4	0.14628 (19)	0.1031 (2)	0.01911 (17)	0.0623 (7)
N5	0.13466 (19)	0.0122 (2)	0.05545 (18)	0.0653 (7)
C1	−0.03854 (16)	0.42678 (18)	0.09166 (16)	0.0379 (5)
C2	−0.12745 (17)	0.4407 (2)	0.07150 (18)	0.0472 (6)
H2	−0.1550	0.4934	0.1000	0.057*
C3	−0.17295 (18)	0.3735 (3)	0.0079 (2)	0.0525 (7)
H3	−0.2325	0.3805	−0.0062	0.063*
C4	−0.13169 (19)	0.2953 (2)	−0.0360 (2)	0.0567 (7)
H4	−0.1646	0.2515	−0.0787	0.068*
C5	−0.04384 (19)	0.2807 (2)	−0.01797 (18)	0.0493 (6)
H5	−0.0163	0.2288	−0.0475	0.059*
C6	0.00111 (16)	0.34824 (19)	0.04711 (16)	0.0387 (5)
C7	0.09879 (16)	0.4373 (2)	0.14406 (17)	0.0417 (6)
C8	0.18438 (18)	0.4695 (3)	0.1936 (2)	0.0620 (8)
H8A	0.1787	0.5340	0.2268	0.093*
H8B	0.2230	0.4808	0.1502	0.093*
H8C	0.2068	0.4147	0.2360	0.093*
C9	0.15636 (18)	0.2894 (2)	0.0572 (2)	0.0509 (7)
H9A	0.1560	0.2934	−0.0086	0.061*
H9B	0.2119	0.3146	0.0878	0.061*
C10	0.13101 (16)	0.1366 (2)	0.16454 (17)	0.0454 (6)
C11	0.1241 (2)	0.1776 (3)	0.25161 (19)	0.0562 (7)
H11	0.1292	0.2497	0.2644	0.067*
C12	0.1096 (2)	0.1053 (3)	0.3164 (2)	0.0637 (9)
H12	0.1046	0.1293	0.3750	0.076*
C13	0.10205 (19)	−0.0044 (3)	0.2980 (2)	0.0668 (9)
H13	0.0923	−0.0508	0.3444	0.080*
C14	0.1089 (2)	−0.0433 (3)	0.2129 (2)	0.0633 (8)
H14	0.1034	−0.1154	0.2002	0.076*
C15	0.12426 (18)	0.0289 (2)	0.14573 (19)	0.0512 (7)
Cl1	−0.11365 (6)	0.69095 (6)	0.19298 (5)	0.0643 (3)

	U11	U22	U33	U12	U13	U23
Zn1	0.0627 (3)	0.0303 (2)	0.0417 (3)	0.000	0.0021 (2)	0.000
N1	0.0454 (11)	0.0342 (10)	0.0424 (11)	−0.0021 (9)	0.0020 (9)	−0.0038 (9)
N2	0.0410 (11)	0.0413 (11)	0.0447 (12)	0.0035 (9)	0.0089 (9)	−0.0003 (9)
N3	0.0578 (14)	0.0496 (13)	0.0404 (12)	0.0149 (11)	0.0118 (10)	−0.0014 (10)
N4	0.0825 (19)	0.0610 (16)	0.0442 (13)	0.0202 (14)	0.0125 (13)	−0.0077 (11)
N5	0.0884 (19)	0.0519 (15)	0.0553 (15)	0.0168 (14)	0.0102 (13)	−0.0051 (12)
C1	0.0421 (13)	0.0353 (11)	0.0356 (12)	−0.0016 (10)	0.0043 (10)	0.0002 (9)
C2	0.0445 (14)	0.0487 (14)	0.0481 (15)	0.0018 (11)	0.0065 (11)	−0.0033 (12)
C3	0.0403 (14)	0.0606 (17)	0.0552 (16)	−0.0069 (13)	0.0038 (12)	−0.0026 (14)
C4	0.0582 (18)	0.0581 (17)	0.0518 (16)	−0.0180 (14)	0.0024 (13)	−0.0129 (13)
C5	0.0578 (17)	0.0447 (14)	0.0461 (14)	−0.0049 (12)	0.0108 (12)	−0.0100 (11)
C6	0.0444 (13)	0.0355 (12)	0.0367 (12)	−0.0022 (10)	0.0078 (10)	0.0021 (9)
C7	0.0410 (13)	0.0404 (13)	0.0427 (13)	−0.0014 (10)	0.0039 (10)	0.0008 (11)
C8	0.0474 (16)	0.070 (2)	0.0648 (19)	−0.0058 (14)	−0.0036 (14)	−0.0091 (16)
C9	0.0498 (15)	0.0562 (16)	0.0497 (15)	0.0084 (13)	0.0172 (12)	0.0017 (13)
C10	0.0432 (13)	0.0531 (15)	0.0397 (13)	0.0127 (12)	0.0062 (11)	0.0013 (11)
C11	0.0612 (18)	0.0644 (18)	0.0431 (15)	0.0068 (14)	0.0089 (13)	−0.0028 (13)
C12	0.0542 (17)	0.098 (3)	0.0389 (15)	0.0078 (17)	0.0077 (13)	0.0052 (16)
C13	0.0517 (17)	0.084 (2)	0.063 (2)	0.0022 (16)	0.0031 (14)	0.0250 (18)
C14	0.0589 (18)	0.0569 (18)	0.071 (2)	0.0042 (15)	0.0001 (15)	0.0115 (16)
C15	0.0485 (15)	0.0522 (16)	0.0514 (15)	0.0120 (12)	0.0033 (12)	0.0016 (13)
Cl1	0.0925 (6)	0.0456 (4)	0.0524 (4)	0.0254 (4)	0.0040 (4)	0.0033 (3)

Zn1—N1i	2.063 (2)	C4—C5	1.377 (4)
Zn1—N1	2.063 (2)	C4—H4	0.9300
Zn1—Cl1i	2.2458 (9)	C5—C6	1.389 (3)
Zn1—Cl1	2.2458 (9)	C5—H5	0.9300
N1—C7	1.321 (3)	C7—C8	1.482 (4)
N1—C1	1.405 (3)	C8—H8A	0.9600
N2—C7	1.359 (3)	C8—H8B	0.9600
N2—C6	1.396 (3)	C8—H8C	0.9600
N2—C9	1.451 (3)	C9—H9A	0.9700
N3—N4	1.360 (3)	C9—H9B	0.9700
N3—C10	1.365 (3)	C10—C15	1.388 (4)
N3—C9	1.449 (3)	C10—C11	1.403 (4)
N4—N5	1.290 (4)	C11—C12	1.366 (4)
N5—C15	1.381 (4)	C11—H11	0.9300
C1—C6	1.390 (3)	C12—C13	1.412 (5)
C1—C2	1.393 (4)	C12—H12	0.9300
C2—C3	1.376 (4)	C13—C14	1.366 (5)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.395 (4)	C14—C15	1.395 (4)
C3—H3	0.9300	C14—H14	0.9300
N1i—Zn1—N1	96.95 (12)	C1—C6—N2	105.2 (2)
N1i—Zn1—Cl1i	109.86 (6)	N1—C7—N2	111.7 (2)
N1—Zn1—Cl1i	114.34 (6)	N1—C7—C8	125.9 (2)
N1i—Zn1—Cl1	114.34 (6)	N2—C7—C8	122.4 (2)
N1—Zn1—Cl1	109.86 (6)	C7—C8—H8A	109.5
Cl1i—Zn1—Cl1	110.89 (5)	C7—C8—H8B	109.5
C7—N1—C1	106.0 (2)	H8A—C8—H8B	109.5
C7—N1—Zn1	127.62 (17)	C7—C8—H8C	109.5
C1—N1—Zn1	125.50 (16)	H8A—C8—H8C	109.5
C7—N2—C6	107.9 (2)	H8B—C8—H8C	109.5
C7—N2—C9	126.5 (2)	N3—C9—N2	111.0 (2)
C6—N2—C9	125.6 (2)	N3—C9—H9A	109.4
N4—N3—C10	110.1 (2)	N2—C9—H9A	109.4
N4—N3—C9	118.6 (2)	N3—C9—H9B	109.4
C10—N3—C9	131.3 (2)	N2—C9—H9B	109.4
N5—N4—N3	109.2 (2)	H9A—C9—H9B	108.0
N4—N5—C15	108.1 (2)	N3—C10—C15	103.8 (2)
C6—C1—C2	119.9 (2)	N3—C10—C11	134.3 (3)
C6—C1—N1	109.2 (2)	C15—C10—C11	121.9 (3)
C2—C1—N1	130.8 (2)	C12—C11—C10	116.0 (3)
C3—C2—C1	117.6 (3)	C12—C11—H11	122.0
C3—C2—H2	121.2	C10—C11—H11	122.0
C1—C2—H2	121.2	C11—C12—C13	122.7 (3)
C2—C3—C4	121.4 (3)	C11—C12—H12	118.7
C2—C3—H3	119.3	C13—C12—H12	118.7
C4—C3—H3	119.3	C14—C13—C12	120.7 (3)
C5—C4—C3	122.1 (3)	C14—C13—H13	119.6
C5—C4—H4	119.0	C12—C13—H13	119.6
C3—C4—H4	119.0	C13—C14—C15	117.7 (3)
C4—C5—C6	115.8 (3)	C13—C14—H14	121.2
C4—C5—H5	122.1	C15—C14—H14	121.2
C6—C5—H5	122.1	N5—C15—C10	108.9 (2)
C5—C6—C1	123.1 (2)	N5—C15—C14	130.1 (3)
C5—C6—N2	131.7 (2)	C10—C15—C14	121.0 (3)
N1i—Zn1—N1—C7	−88.2 (2)	Zn1—N1—C7—N2	169.67 (16)
Cl1i—Zn1—N1—C7	27.3 (2)	C1—N1—C7—C8	178.9 (3)
Cl1—Zn1—N1—C7	152.8 (2)	Zn1—N1—C7—C8	−11.2 (4)
N1i—Zn1—N1—C1	79.87 (19)	C6—N2—C7—N1	0.2 (3)
Cl1i—Zn1—N1—C1	−164.61 (17)	C9—N2—C7—N1	−178.6 (2)
Cl1—Zn1—N1—C1	−39.2 (2)	C6—N2—C7—C8	−179.0 (3)
C10—N3—N4—N5	−0.1 (3)	C9—N2—C7—C8	2.2 (4)
C9—N3—N4—N5	180.0 (3)	N4—N3—C9—N2	129.2 (3)
N3—N4—N5—C15	0.4 (4)	C10—N3—C9—N2	−50.8 (4)
C7—N1—C1—C6	0.1 (3)	C7—N2—C9—N3	115.7 (3)
Zn1—N1—C1—C6	−170.04 (15)	C6—N2—C9—N3	−62.9 (3)
C7—N1—C1—C2	−179.1 (3)	N4—N3—C10—C15	−0.3 (3)
Zn1—N1—C1—C2	10.7 (4)	C9—N3—C10—C15	179.7 (3)
C6—C1—C2—C3	0.9 (4)	N4—N3—C10—C11	179.5 (3)
N1—C1—C2—C3	−179.9 (3)	C9—N3—C10—C11	−0.6 (5)
C1—C2—C3—C4	−0.9 (4)	N3—C10—C11—C12	179.7 (3)
C2—C3—C4—C5	0.2 (5)	C15—C10—C11—C12	−0.6 (4)
C3—C4—C5—C6	0.5 (4)	C10—C11—C12—C13	0.1 (4)
C4—C5—C6—C1	−0.5 (4)	C11—C12—C13—C14	−0.2 (5)
C4—C5—C6—N2	−179.9 (3)	C12—C13—C14—C15	0.6 (4)
C2—C1—C6—C5	−0.2 (4)	N4—N5—C15—C10	−0.6 (3)
N1—C1—C6—C5	−179.5 (2)	N4—N5—C15—C14	179.0 (3)
C2—C1—C6—N2	179.4 (2)	N3—C10—C15—N5	0.6 (3)
N1—C1—C6—N2	0.0 (3)	C11—C10—C15—N5	−179.3 (3)
C7—N2—C6—C5	179.3 (3)	N3—C10—C15—C14	−179.1 (3)
C9—N2—C6—C5	−1.8 (4)	C11—C10—C15—C14	1.1 (4)
C7—N2—C6—C1	−0.1 (3)	C13—C14—C15—N5	179.4 (3)
C9—N2—C6—C1	178.7 (2)	C13—C14—C15—C10	−1.0 (4)
C1—N1—C7—N2	−0.2 (3)