[2-(1H-Benzimidazol-2-yl-κN)aniline-κN]dichloridozinc.

In the title benzimidazole mononuclear complex, [ZnCl(2)(C(13)H(11)N(3))], the Zn(II) ion is four-coordinated in a distorted tetra-hedral geometry by an imidazole N, an amino N and two Cl atoms. The dihedral angle between the benzimidazole and benzene rings is 9.57 (1)°. In the crystal, mol-ecules are linked by weak N-H⋯Cl hydrogen bonds into layers parallel to the bc plane. π-π inter-actions with centroid-centroid distances in the range 3.4452 (8)-3.8074 (8) Å are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to benzimidazoles and their applications, see: Chassaing et al. (2008 ▶); Podunavac-Kuzmonovic et al. (1999 ▶); Xue et al. (2011 ▶). For related structures, see: Eltayeb et al. (2007 ▶; 2009 ▶; 2011 ▶); Maldonado-Rogado et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[ZnCl2(C13H11N3)]

M = 345.54

Monoclinic,

a = 22.0252 (7) Å

b = 10.0651 (3) Å

c = 15.3676 (6) Å

β = 125.244 (2)°

V = 2782.32 (18) Å3

Z = 8

Mo Kα radiation

μ = 2.14 mm−1

T = 100 K

0.48 × 0.31 × 0.31 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.428, T max = 0.560

50659 measured reflections

7344 independent reflections

5887 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.081

S = 1.02

7344 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026572/rz2622sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026572/rz2622Isup2.hkl

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

[ZnCl2(C13H11N3)]	F(000) = 1392
Mr = 345.54	Dx = 1.650 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7344 reflections
a = 22.0252 (7) Å	θ = 2.3–37.7°
b = 10.0651 (3) Å	µ = 2.14 mm−1
c = 15.3676 (6) Å	T = 100 K
β = 125.244 (2)°	Block, yellow
V = 2782.32 (18) Å3	0.48 × 0.31 × 0.31 mm
Z = 8

Bruker APEX DUO CCD area-detector diffractometer	7344 independent reflections
Radiation source: sealed tube	5887 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 37.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −37→36
Tmin = 0.428, Tmax = 0.560	k = −17→17
50659 measured reflections	l = −25→26

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0419P)2 + 0.7801P] where P = (Fo2 + 2Fc2)/3
7344 reflections	(Δ/σ)max = 0.002
172 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.057453 (6)	0.825871 (11)	0.151068 (9)	0.03470 (4)
Cl1	0.094347 (18)	0.82859 (2)	0.04109 (2)	0.04377 (6)
Cl2	0.121812 (17)	0.94430 (3)	0.29852 (2)	0.04885 (7)
N1	0.03795 (5)	0.63755 (8)	0.17124 (6)	0.03277 (14)
N2	−0.01309 (5)	0.43948 (8)	0.11361 (7)	0.03566 (16)
H1N2	−0.0400	0.3776	0.0772	0.043*
N3	−0.05430 (5)	0.86317 (8)	0.06474 (7)	0.03630 (16)
H1N3	−0.0613	0.9453	0.0395	0.044*
H2N3	−0.0606	0.8661	0.1203	0.044*
C1	0.08602 (5)	0.54368 (9)	0.24599 (8)	0.03401 (16)
C2	0.15487 (6)	0.55968 (12)	0.34379 (9)	0.0441 (2)
H2A	0.1765	0.6429	0.3686	0.053*
C3	0.18917 (8)	0.44533 (15)	0.40179 (11)	0.0548 (3)
H3A	0.2351	0.4519	0.4673	0.066*
C4	0.15673 (9)	0.32000 (14)	0.36457 (13)	0.0578 (3)
H4A	0.1816	0.2457	0.4063	0.069*
C5	0.08893 (8)	0.30296 (12)	0.26782 (11)	0.0487 (3)
H5A	0.0677	0.2195	0.2428	0.058*
C6	0.05428 (6)	0.41848 (9)	0.20999 (8)	0.03638 (18)
C7	−0.02133 (5)	0.57180 (8)	0.09356 (7)	0.03092 (15)
C8	−0.08750 (5)	0.62967 (9)	−0.00210 (7)	0.03133 (15)
C9	−0.13949 (6)	0.54428 (11)	−0.08355 (9)	0.0409 (2)
H9A	−0.1313	0.4531	−0.0751	0.049*
C10	−0.20257 (7)	0.59227 (14)	−0.17600 (10)	0.0501 (3)
H10A	−0.2366	0.5336	−0.2286	0.060*
C11	−0.21502 (7)	0.72704 (15)	−0.19038 (10)	0.0556 (3)
H11A	−0.2567	0.7598	−0.2535	0.067*
C12	−0.16525 (7)	0.81339 (12)	−0.11062 (10)	0.0478 (3)
H12A	−0.1741	0.9043	−0.1203	0.057*
C13	−0.10222 (5)	0.76671 (9)	−0.01632 (7)	0.03314 (16)

	U11	U22	U33	U12	U13	U23
Zn1	0.03589 (6)	0.02529 (5)	0.03528 (6)	−0.00291 (3)	0.01612 (5)	−0.00044 (3)
Cl1	0.05837 (16)	0.03021 (11)	0.04711 (13)	−0.00299 (9)	0.03297 (13)	0.00024 (8)
Cl2	0.05149 (15)	0.04321 (13)	0.04471 (13)	−0.01328 (11)	0.02364 (11)	−0.01315 (10)
N1	0.0341 (3)	0.0252 (3)	0.0324 (3)	−0.0009 (3)	0.0154 (3)	0.0028 (2)
N2	0.0392 (4)	0.0235 (3)	0.0404 (4)	−0.0010 (3)	0.0207 (3)	0.0010 (3)
N3	0.0372 (4)	0.0252 (3)	0.0366 (4)	0.0020 (3)	0.0156 (3)	−0.0006 (3)
C1	0.0358 (4)	0.0293 (4)	0.0345 (4)	0.0030 (3)	0.0188 (3)	0.0054 (3)
C2	0.0390 (5)	0.0421 (5)	0.0387 (5)	0.0026 (4)	0.0153 (4)	0.0045 (4)
C3	0.0460 (6)	0.0552 (7)	0.0454 (6)	0.0125 (5)	0.0162 (5)	0.0139 (5)
C4	0.0568 (7)	0.0461 (7)	0.0588 (7)	0.0189 (5)	0.0266 (6)	0.0219 (5)
C5	0.0541 (6)	0.0299 (4)	0.0586 (7)	0.0101 (4)	0.0306 (6)	0.0126 (4)
C6	0.0405 (4)	0.0275 (4)	0.0413 (4)	0.0039 (3)	0.0237 (4)	0.0055 (3)
C7	0.0345 (4)	0.0238 (3)	0.0331 (4)	−0.0006 (3)	0.0187 (3)	0.0011 (3)
C8	0.0316 (4)	0.0280 (3)	0.0313 (3)	−0.0009 (3)	0.0163 (3)	−0.0002 (3)
C9	0.0391 (5)	0.0345 (4)	0.0406 (5)	−0.0050 (4)	0.0180 (4)	−0.0065 (4)
C10	0.0374 (5)	0.0505 (6)	0.0421 (5)	−0.0056 (4)	0.0112 (4)	−0.0100 (5)
C11	0.0369 (5)	0.0533 (7)	0.0440 (6)	0.0034 (5)	0.0045 (4)	−0.0008 (5)
C12	0.0372 (5)	0.0385 (5)	0.0438 (5)	0.0061 (4)	0.0095 (4)	0.0038 (4)
C13	0.0307 (4)	0.0288 (4)	0.0334 (4)	0.0015 (3)	0.0147 (3)	0.0007 (3)

Zn1—N1	2.0068 (8)	C3—H3A	0.9300
Zn1—N3	2.0471 (9)	C4—C5	1.381 (2)
Zn1—Cl2	2.2041 (3)	C4—H4A	0.9300
Zn1—Cl1	2.2589 (3)	C5—C6	1.3933 (14)
N1—C7	1.3300 (12)	C5—H5A	0.9300
N1—C1	1.3890 (12)	C7—C8	1.4668 (12)
N2—C7	1.3554 (12)	C8—C9	1.4009 (13)
N2—C6	1.3798 (13)	C8—C13	1.4049 (13)
N2—H1N2	0.8188	C9—C10	1.3797 (16)
N3—C13	1.4460 (12)	C9—H9A	0.9300
N3—H1N3	0.8877	C10—C11	1.376 (2)
N3—H2N3	0.9418	C10—H10A	0.9300
C1—C6	1.3916 (14)	C11—C12	1.3816 (18)
C1—C2	1.3978 (15)	C11—H11A	0.9300
C2—C3	1.3830 (17)	C12—C13	1.3878 (14)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.399 (2)
N1—Zn1—N3	89.36 (3)	C3—C4—H4A	118.9
N1—Zn1—Cl2	114.83 (3)	C4—C5—C6	115.92 (12)
N3—Zn1—Cl2	112.74 (3)	C4—C5—H5A	122.0
N1—Zn1—Cl1	109.18 (3)	C6—C5—H5A	122.0
N3—Zn1—Cl1	109.27 (3)	N2—C6—C1	105.68 (8)
Cl2—Zn1—Cl1	117.844 (13)	N2—C6—C5	131.80 (10)
C7—N1—C1	106.79 (8)	C1—C6—C5	122.52 (10)
C7—N1—Zn1	121.20 (6)	N1—C7—N2	110.58 (8)
C1—N1—Zn1	129.89 (7)	N1—C7—C8	126.51 (8)
C7—N2—C6	108.33 (8)	N2—C7—C8	122.91 (8)
C7—N2—H1N2	130.1	C9—C8—C13	117.84 (9)
C6—N2—H1N2	121.5	C9—C8—C7	118.62 (9)
C13—N3—Zn1	116.24 (6)	C13—C8—C7	123.53 (8)
C13—N3—H1N3	113.1	C10—C9—C8	121.57 (10)
Zn1—N3—H1N3	107.2	C10—C9—H9A	119.2
C13—N3—H2N3	112.7	C8—C9—H9A	119.2
Zn1—N3—H2N3	99.8	C11—C10—C9	119.95 (10)
H1N3—N3—H2N3	106.7	C11—C10—H10A	120.0
N1—C1—C6	108.60 (8)	C9—C10—H10A	120.0
N1—C1—C2	130.32 (9)	C10—C11—C12	119.67 (11)
C6—C1—C2	121.07 (9)	C10—C11—H11A	120.2
C3—C2—C1	116.57 (11)	C12—C11—H11A	120.2
C3—C2—H2A	121.7	C11—C12—C13	121.13 (11)
C1—C2—H2A	121.7	C11—C12—H12A	119.4
C2—C3—C4	121.78 (12)	C13—C12—H12A	119.4
C2—C3—H3A	119.1	C12—C13—C8	119.79 (9)
C4—C3—H3A	119.1	C12—C13—N3	117.73 (9)
C5—C4—C3	122.13 (11)	C8—C13—N3	122.48 (8)
C5—C4—H4A	118.9
N3—Zn1—N1—C7	37.88 (8)	C4—C5—C6—C1	0.90 (19)
Cl2—Zn1—N1—C7	152.76 (7)	C1—N1—C7—N2	−1.27 (11)
Cl1—Zn1—N1—C7	−72.34 (8)	Zn1—N1—C7—N2	163.70 (7)
N3—Zn1—N1—C1	−160.99 (9)	C1—N1—C7—C8	178.98 (9)
Cl2—Zn1—N1—C1	−46.11 (10)	Zn1—N1—C7—C8	−16.04 (14)
Cl1—Zn1—N1—C1	88.79 (9)	C6—N2—C7—N1	1.11 (12)
N1—Zn1—N3—C13	−47.06 (7)	C6—N2—C7—C8	−179.14 (9)
Cl2—Zn1—N3—C13	−163.85 (6)	N1—C7—C8—C9	170.17 (10)
Cl1—Zn1—N3—C13	63.07 (7)	N2—C7—C8—C9	−9.55 (15)
C7—N1—C1—C6	0.96 (11)	N1—C7—C8—C13	−10.56 (16)
Zn1—N1—C1—C6	−162.24 (7)	N2—C7—C8—C13	169.73 (10)
C7—N1—C1—C2	−177.97 (12)	C13—C8—C9—C10	1.27 (17)
Zn1—N1—C1—C2	18.82 (17)	C7—C8—C9—C10	−179.41 (11)
N1—C1—C2—C3	178.91 (12)	C8—C9—C10—C11	0.9 (2)
C6—C1—C2—C3	0.09 (18)	C9—C10—C11—C12	−1.9 (2)
C1—C2—C3—C4	0.0 (2)	C10—C11—C12—C13	0.7 (2)
C2—C3—C4—C5	0.3 (3)	C11—C12—C13—C8	1.5 (2)
C3—C4—C5—C6	−0.8 (2)	C11—C12—C13—N3	−177.82 (13)
C7—N2—C6—C1	−0.46 (11)	C9—C8—C13—C12	−2.43 (16)
C7—N2—C6—C5	178.79 (13)	C7—C8—C13—C12	178.29 (11)
N1—C1—C6—N2	−0.30 (11)	C9—C8—C13—N3	176.84 (10)
C2—C1—C6—N2	178.75 (10)	C7—C8—C13—N3	−2.44 (15)
N1—C1—C6—C5	−179.64 (11)	Zn1—N3—C13—C12	−143.37 (10)
C2—C1—C6—C5	−0.59 (18)	Zn1—N3—C13—C8	37.35 (12)
C4—C5—C6—N2	−178.24 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Cl1i	0.82	2.56	3.3503 (9)	164
N3—H1N3···Cl1ii	0.89	2.49	3.3753 (9)	174
N3—H2N3···Cl2iii	0.94	2.44	3.3015 (12)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯Cl1i	0.82	2.56	3.3503 (9)	164
N3—H1N3⋯Cl1ii	0.89	2.49	3.3753 (9)	174
N3—H2N3⋯Cl2iii	0.94	2.44	3.3015 (12)	153

Symmetry codes: (i) ; (ii) ; (iii) .