Bis(1-benzyl-1H-benzimidazole-κN (3))di-chlorido-zinc.

In the title compound, [ZnCl2(C14H12N2)2], the Zn(II) atom exhibits a distorted tetra-hedral coordination geometry involving two chloride anions and two N-atom donors from 1-benzyl-1H-benzimidazole ligands. In both ligands, the benzyl and benzimidazole rings are nearly perpendicular [dihedral angles = 81.7 (2) and 81.5 (2)°]. The two benzimidazole systems are essentially planar [maximum deviations = 0.015 (3) and 0.020 (2) Å] and form a dihedral angle of 78.09 (8)°. In the crystal, centrosymmetrically related mol-ecules are linked by pairs of C-H⋯Cl hydrogen bonds into chains parallel to the a axis.

Related literature

For background to the biochemical properties of benzimidazole derivatives, see: Mann et al. (2001 ▶); Naithani et al. (1990 ▶); Goudgaon et al. (2004 ▶). For the structures of related compounds see: Abdel-Ghani & Mansour (2011 ▶, 2012 ▶); Ahuja & Prasad (1976 ▶).

Experimental

Crystal data

[ZnCl2(C14H12N2)2]

M = 552.78

Triclinic,

a = 9.9819 (4) Å

b = 10.0564 (4) Å

c = 13.6641 (6) Å

α = 99.539 (2)°

β = 92.087 (2)°

γ = 99.122 (2)°

V = 1332.79 (10) Å3

Z = 2

Mo Kα radiation

μ = 1.15 mm−1

T = 296 K

0.37 × 0.32 × 0.26 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.682, T max = 0.840

30968 measured reflections

7403 independent reflections

5928 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.06

7403 reflections

318 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814002840/rz5104sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002840/rz5104Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

[ZnCl2(C14H12N2)2]	V = 1332.79 (10) Å3
Mr = 552.78	Z = 2
Triclinic, P1	F(000) = 568
Hall symbol: -p 1	Dx = 1.377 Mg m−3
a = 9.9819 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0564 (4) Å	µ = 1.15 mm−1
c = 13.6641 (6) Å	T = 296 K
α = 99.539 (2)°	Block, colourless
β = 92.087 (2)°	0.37 × 0.32 × 0.26 mm
γ = 99.122 (2)°

Bruker X8 APEX diffractometer	7403 independent reflections
Radiation source: fine-focus sealed tube	5928 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 29.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.682, Tmax = 0.840	k = −13→13
30968 measured reflections	l = −18→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0551P)2 + 0.3641P] where P = (Fo2 + 2Fc2)/3
7403 reflections	(Δ/σ)max < 0.001
318 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.7633 (4)	0.8525 (3)	0.4366 (3)	0.1008 (11)
H1	0.7791	0.9301	0.4072	0.121*
C2	0.8206 (5)	0.8556 (4)	0.5311 (3)	0.1210 (14)
H2	0.8754	0.9350	0.5641	0.145*
C3	0.7979 (4)	0.7450 (5)	0.5757 (2)	0.1088 (13)
H3	0.8379	0.7477	0.6387	0.131*
C4	0.7162 (4)	0.6296 (4)	0.5281 (3)	0.1052 (12)
H4	0.6985	0.5537	0.5593	0.126*
C5	0.6591 (4)	0.6246 (3)	0.4331 (2)	0.0826 (8)
H5	0.6036	0.5451	0.4010	0.099*
C6	0.6835 (2)	0.7356 (2)	0.38635 (17)	0.0602 (5)
C7	0.6298 (3)	0.7325 (3)	0.28114 (18)	0.0675 (6)
H7A	0.6199	0.8247	0.2733	0.085 (9)*
H7B	0.6962	0.7031	0.2359	0.084 (9)*
C8	0.3754 (2)	0.6587 (2)	0.29074 (15)	0.0539 (5)
C9	0.3381 (3)	0.7496 (3)	0.36933 (17)	0.0692 (6)
H9	0.4018	0.8181	0.4071	0.083*
C10	0.2033 (4)	0.7334 (3)	0.3883 (2)	0.0799 (8)
H10	0.1754	0.7914	0.4411	0.096*
C11	0.1069 (3)	0.6330 (3)	0.3312 (2)	0.0775 (7)
H11	0.0163	0.6255	0.3465	0.093*
C12	0.1428 (3)	0.5448 (3)	0.25247 (19)	0.0644 (6)
H12	0.0780	0.4784	0.2138	0.077*
C13	0.2792 (2)	0.5583 (2)	0.23266 (15)	0.0510 (4)
C14	0.4755 (2)	0.5385 (2)	0.17551 (15)	0.0538 (5)
H14	0.5432	0.5085	0.1369	0.065*
C15	−0.2428 (3)	0.2655 (3)	0.2558 (2)	0.0821 (8)
H15	−0.1617	0.3181	0.2437	0.099*
C16	−0.2920 (5)	0.2837 (4)	0.3495 (2)	0.1078 (12)
H16	−0.2421	0.3458	0.4010	0.129*
C17	−0.4137 (4)	0.2106 (5)	0.3665 (2)	0.1047 (13)
H17	−0.4492	0.2271	0.4285	0.126*
C18	−0.4834 (3)	0.1131 (4)	0.2925 (2)	0.0917 (10)
H18	−0.5648	0.0613	0.3049	0.110*
C19	−0.4329 (2)	0.0915 (3)	0.19898 (18)	0.0638 (6)
H19	−0.4797	0.0243	0.1490	0.077*
C20	−0.3139 (2)	0.1694 (2)	0.18024 (15)	0.0487 (4)
C21	−0.26224 (18)	0.1483 (2)	0.07709 (15)	0.0491 (4)
H21A	−0.3058	0.0600	0.0407	0.059*
H21B	−0.2862	0.2182	0.0418	0.059*
C22	−0.04380 (18)	0.06922 (18)	0.12376 (13)	0.0409 (4)
C23	−0.0871 (2)	−0.0469 (2)	0.16412 (17)	0.0570 (5)
H23	−0.1788	−0.0802	0.1678	0.068*
C24	0.0132 (3)	−0.1098 (2)	0.1982 (2)	0.0688 (6)
H24	−0.0113	−0.1878	0.2261	0.083*
C25	0.1510 (3)	−0.0600 (2)	0.19231 (18)	0.0638 (6)
H25	0.2157	−0.1056	0.2166	0.077*
C26	0.1940 (2)	0.0551 (2)	0.15140 (15)	0.0510 (4)
H26	0.2858	0.0878	0.1472	0.061*
C27	0.09351 (18)	0.11926 (18)	0.11694 (12)	0.0393 (3)
C28	−0.02314 (18)	0.24853 (19)	0.05074 (14)	0.0447 (4)
H28	−0.0461	0.3176	0.0191	0.054*
N1	0.49942 (19)	0.6426 (2)	0.25291 (13)	0.0562 (4)
N2	0.34613 (17)	0.48349 (18)	0.16007 (13)	0.0515 (4)
N3	0.10356 (15)	0.23339 (16)	0.07047 (12)	0.0443 (3)
N4	−0.11488 (15)	0.15456 (16)	0.08096 (12)	0.0425 (3)
Zn1	0.26873 (2)	0.35268 (2)	0.034848 (16)	0.04370 (8)
Cl1	0.18906 (5)	0.46699 (5)	−0.07679 (4)	0.05779 (14)
Cl2	0.43183 (5)	0.23659 (6)	−0.01957 (4)	0.05514 (13)

	U11	U22	U33	U12	U13	U23
C1	0.128 (3)	0.0754 (18)	0.082 (2)	−0.0178 (19)	−0.027 (2)	0.0067 (16)
C2	0.147 (4)	0.105 (3)	0.085 (2)	−0.009 (2)	−0.049 (2)	−0.015 (2)
C3	0.131 (3)	0.130 (3)	0.0621 (17)	0.044 (3)	−0.0313 (19)	−0.005 (2)
C4	0.139 (3)	0.101 (2)	0.081 (2)	0.032 (2)	−0.024 (2)	0.0289 (19)
C5	0.105 (2)	0.0691 (16)	0.0702 (16)	0.0086 (15)	−0.0213 (15)	0.0133 (13)
C6	0.0603 (13)	0.0638 (13)	0.0514 (11)	0.0031 (10)	−0.0037 (10)	0.0035 (10)
C7	0.0673 (14)	0.0725 (15)	0.0551 (12)	−0.0147 (12)	−0.0033 (11)	0.0164 (11)
C8	0.0656 (13)	0.0573 (11)	0.0423 (10)	0.0116 (10)	−0.0011 (9)	0.0186 (8)
C9	0.0940 (19)	0.0659 (14)	0.0497 (12)	0.0184 (13)	−0.0031 (12)	0.0124 (10)
C10	0.107 (2)	0.0841 (18)	0.0608 (14)	0.0472 (17)	0.0141 (15)	0.0157 (13)
C11	0.0728 (16)	0.094 (2)	0.0791 (17)	0.0406 (15)	0.0165 (14)	0.0269 (15)
C12	0.0562 (12)	0.0737 (15)	0.0688 (14)	0.0189 (11)	0.0059 (11)	0.0198 (12)
C13	0.0550 (11)	0.0539 (11)	0.0479 (10)	0.0116 (9)	0.0019 (8)	0.0177 (8)
C14	0.0516 (11)	0.0620 (12)	0.0454 (10)	−0.0021 (9)	0.0040 (8)	0.0136 (9)
C15	0.090 (2)	0.0796 (18)	0.0657 (15)	−0.0004 (15)	0.0121 (14)	−0.0051 (13)
C16	0.128 (3)	0.124 (3)	0.0638 (18)	0.033 (3)	0.0048 (19)	−0.0162 (18)
C17	0.099 (2)	0.178 (4)	0.0517 (15)	0.064 (3)	0.0180 (16)	0.0198 (19)
C18	0.0571 (15)	0.161 (3)	0.0696 (17)	0.0273 (18)	0.0195 (13)	0.045 (2)
C19	0.0406 (10)	0.0944 (17)	0.0597 (12)	0.0133 (11)	0.0059 (9)	0.0199 (12)
C20	0.0455 (10)	0.0543 (11)	0.0502 (10)	0.0158 (8)	0.0057 (8)	0.0124 (8)
C21	0.0338 (8)	0.0610 (11)	0.0525 (10)	0.0051 (8)	0.0037 (7)	0.0129 (9)
C22	0.0399 (8)	0.0422 (9)	0.0400 (8)	0.0031 (7)	−0.0006 (7)	0.0099 (7)
C23	0.0510 (11)	0.0547 (11)	0.0668 (13)	−0.0035 (9)	0.0029 (9)	0.0267 (10)
C24	0.0727 (15)	0.0575 (13)	0.0822 (16)	0.0032 (11)	−0.0030 (12)	0.0387 (12)
C25	0.0673 (14)	0.0640 (13)	0.0676 (14)	0.0189 (11)	−0.0075 (11)	0.0279 (11)
C26	0.0440 (10)	0.0595 (11)	0.0519 (10)	0.0106 (8)	−0.0034 (8)	0.0160 (9)
C27	0.0400 (8)	0.0402 (8)	0.0375 (8)	0.0043 (7)	−0.0002 (6)	0.0092 (7)
C28	0.0408 (9)	0.0429 (9)	0.0539 (10)	0.0070 (7)	0.0038 (8)	0.0182 (8)
N1	0.0570 (10)	0.0648 (11)	0.0434 (8)	−0.0043 (8)	−0.0011 (7)	0.0144 (8)
N2	0.0464 (9)	0.0572 (10)	0.0502 (9)	0.0023 (7)	0.0031 (7)	0.0129 (7)
N3	0.0377 (7)	0.0442 (8)	0.0539 (9)	0.0042 (6)	0.0031 (6)	0.0189 (7)
N4	0.0359 (7)	0.0451 (8)	0.0479 (8)	0.0051 (6)	0.0031 (6)	0.0140 (6)
Zn1	0.03618 (11)	0.04504 (13)	0.05179 (14)	0.00320 (8)	0.00320 (8)	0.01722 (9)
Cl1	0.0506 (3)	0.0594 (3)	0.0722 (3)	0.0134 (2)	0.0037 (2)	0.0330 (3)
Cl2	0.0428 (2)	0.0630 (3)	0.0643 (3)	0.0156 (2)	0.0044 (2)	0.0178 (2)

C1—C6	1.373 (4)	C15—H15	0.9300
C1—C2	1.386 (5)	C16—C17	1.365 (6)
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.347 (6)	C17—C18	1.368 (5)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.359 (5)	C18—C19	1.387 (4)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.388 (4)	C19—C20	1.372 (3)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.370 (4)	C20—C21	1.512 (3)
C5—H5	0.9300	C21—N4	1.461 (2)
C6—C7	1.509 (3)	C21—H21A	0.9700
C7—N1	1.461 (3)	C21—H21B	0.9700
C7—H7A	0.9700	C22—N4	1.382 (2)
C7—H7B	0.9700	C22—C23	1.387 (3)
C8—N1	1.381 (3)	C22—C27	1.395 (2)
C8—C9	1.393 (3)	C23—C24	1.372 (3)
C8—C13	1.394 (3)	C23—H23	0.9300
C9—C10	1.369 (4)	C24—C25	1.398 (4)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.389 (4)	C25—C26	1.382 (3)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.373 (4)	C26—C27	1.384 (3)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.387 (3)	C27—N3	1.393 (2)
C12—H12	0.9300	C28—N3	1.321 (2)
C13—N2	1.398 (3)	C28—N4	1.336 (2)
C14—N2	1.316 (3)	C28—H28	0.9300
C14—N1	1.344 (3)	N2—Zn1	2.0225 (17)
C14—H14	0.9300	N3—Zn1	2.0048 (15)
C15—C20	1.380 (3)	Zn1—Cl2	2.2292 (5)
C15—C16	1.382 (4)	Zn1—Cl1	2.2503 (5)
C6—C1—C2	120.4 (3)	C17—C18—C19	120.1 (3)
C6—C1—H1	119.8	C17—C18—H18	120.0
C2—C1—H1	119.8	C19—C18—H18	120.0
C3—C2—C1	120.9 (3)	C20—C19—C18	120.0 (3)
C3—C2—H2	119.6	C20—C19—H19	120.0
C1—C2—H2	119.6	C18—C19—H19	120.0
C2—C3—C4	119.6 (3)	C19—C20—C15	119.6 (2)
C2—C3—H3	120.2	C19—C20—C21	119.6 (2)
C4—C3—H3	120.2	C15—C20—C21	120.8 (2)
C3—C4—C5	120.2 (3)	N4—C21—C20	111.42 (16)
C3—C4—H4	119.9	N4—C21—H21A	109.3
C5—C4—H4	119.9	C20—C21—H21A	109.3
C6—C5—C4	120.7 (3)	N4—C21—H21B	109.3
C6—C5—H5	119.6	C20—C21—H21B	109.3
C4—C5—H5	119.6	H21A—C21—H21B	108.0
C5—C6—C1	118.3 (3)	N4—C22—C23	131.75 (17)
C5—C6—C7	122.6 (2)	N4—C22—C27	105.86 (15)
C1—C6—C7	119.2 (2)	C23—C22—C27	122.35 (17)
N1—C7—C6	114.19 (19)	C24—C23—C22	116.2 (2)
N1—C7—H7A	108.7	C24—C23—H23	121.9
C6—C7—H7A	108.7	C22—C23—H23	121.9
N1—C7—H7B	108.7	C23—C24—C25	121.9 (2)
C6—C7—H7B	108.7	C23—C24—H24	119.0
H7A—C7—H7B	107.6	C25—C24—H24	119.0
N1—C8—C9	132.6 (2)	C26—C25—C24	121.8 (2)
N1—C8—C13	106.03 (19)	C26—C25—H25	119.1
C9—C8—C13	121.4 (2)	C24—C25—H25	119.1
C10—C9—C8	116.9 (3)	C25—C26—C27	116.63 (19)
C10—C9—H9	121.6	C25—C26—H26	121.7
C8—C9—H9	121.6	C27—C26—H26	121.7
C9—C10—C11	122.0 (3)	C26—C27—N3	130.31 (17)
C9—C10—H10	119.0	C26—C27—C22	121.08 (17)
C11—C10—H10	119.0	N3—C27—C22	108.59 (15)
C12—C11—C10	121.3 (3)	N3—C28—N4	113.13 (16)
C12—C11—H11	119.4	N3—C28—H28	123.4
C10—C11—H11	119.4	N4—C28—H28	123.4
C11—C12—C13	117.7 (3)	C14—N1—C8	107.04 (18)
C11—C12—H12	121.2	C14—N1—C7	125.4 (2)
C13—C12—H12	121.2	C8—N1—C7	127.1 (2)
C12—C13—C8	120.7 (2)	C14—N2—C13	105.48 (18)
C12—C13—N2	130.8 (2)	C14—N2—Zn1	123.26 (15)
C8—C13—N2	108.46 (19)	C13—N2—Zn1	129.57 (14)
N2—C14—N1	113.0 (2)	C28—N3—C27	105.30 (14)
N2—C14—H14	123.5	C28—N3—Zn1	124.79 (12)
N1—C14—H14	123.5	C27—N3—Zn1	129.89 (12)
C20—C15—C16	120.0 (3)	C28—N4—C22	107.12 (15)
C20—C15—H15	120.0	C28—N4—C21	126.89 (16)
C16—C15—H15	120.0	C22—N4—C21	125.84 (15)
C17—C16—C15	120.2 (3)	N3—Zn1—N2	107.29 (7)
C17—C16—H16	119.9	N3—Zn1—Cl2	113.31 (5)
C15—C16—H16	119.9	N2—Zn1—Cl2	107.21 (5)
C16—C17—C18	120.1 (3)	N3—Zn1—Cl1	104.56 (5)
C16—C17—H17	119.9	N2—Zn1—Cl1	110.42 (5)
C18—C17—H17	119.9	Cl2—Zn1—Cl1	113.88 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cl1i	0.93	2.81	3.660 (2)	153
C28—H28···Cl1ii	0.93	2.80	3.502 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cl1i	0.93	2.81	3.660 (2)	153
C28—H28⋯Cl1ii	0.93	2.80	3.502 (2)	133

Symmetry codes: (i) ; (ii) .