Bis[μ(2)-1,2-bis-(imidazol-1-ylmeth-yl)benzene-κN:N]bis-[dichloridozinc(II)].

In the crystal structure of the centrosymmetric title compound, [Zn(2)Cl(4)(C(14)H(14)N(4))(2)], the Zn(II) atom is coordinated by two N atoms from two 1,2-bis-(imidazol-1-ylmeth-yl)benzene ligands and two Cl atoms to confer a distorted tetra-hedral geometry at the metal center.

Related literature

For conformationally flexible ligands and their metal complexes, see: Carlucci et al. (2004 ▶); Fan et al. (2005 ▶); Hennigar et al. (1997 ▶). For metal complexes of similar ligands, see: Liu et al. (2007 ▶); Moulton & Zaworotko (2001 ▶); Tan et al. (2004 ▶).

Experimental

Crystal data

[Zn2Cl4(C14H14N4)2]

M = 749.12

Triclinic,

a = 8.5502 (12) Å

b = 8.7267 (13) Å

c = 11.5726 (17) Å

α = 102.824 (2)°

β = 105.720 (2)°

γ = 91.763 (2)°

V = 806.6 (2) Å3

Z = 1

Mo Kα radiation

μ = 1.85 mm−1

T = 291 K

0.20 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.709, T max = 0.809

6327 measured reflections

3130 independent reflections

2912 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.084

S = 1.09

3130 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027044/ng2598sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027044/ng2598Isup2.hkl

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

[Zn2Cl4(C14H14N4)2]	Z = 1
Mr = 749.12	F(000) = 380
Triclinic, P1	Dx = 1.542 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5502 (12) Å	Cell parameters from 3130 reflections
b = 8.7267 (13) Å	θ = 1.9–26.0°
c = 11.5726 (17) Å	µ = 1.85 mm−1
α = 102.824 (2)°	T = 291 K
β = 105.720 (2)°	Block, white
γ = 91.763 (2)°	0.20 × 0.15 × 0.12 mm
V = 806.6 (2) Å3

Bruker SMART APEX CCD diffractometer	3130 independent reflections
Radiation source: fine-focus sealed tube	2912 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.709, Tmax = 0.809	k = −10→10
6327 measured reflections	l = −13→14

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.3649P] where P = (Fo2 + 2Fc2)/3
3130 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.27 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
Zn1	0.77170 (3)	0.60926 (3)	0.29452 (3)	0.03231 (11)
Cl1	0.67332 (9)	0.68391 (9)	0.11848 (6)	0.04696 (19)
Cl2	1.02202 (9)	0.52603 (9)	0.32757 (7)	0.04806 (19)
N1	0.6030 (3)	0.4485 (3)	0.2991 (2)	0.0369 (5)
N2	0.2055 (3)	0.2012 (2)	0.56368 (19)	0.0345 (5)
N3	0.3737 (3)	0.2956 (2)	0.2378 (2)	0.0348 (5)
N4	0.1141 (3)	0.0502 (3)	0.37642 (19)	0.0355 (5)
C1	0.1171 (3)	−0.0585 (3)	0.1590 (2)	0.0354 (6)
C2	0.2061 (3)	0.0452 (3)	0.1196 (2)	0.0340 (6)
C3	0.1073 (3)	0.1879 (3)	0.4517 (2)	0.0360 (6)
H3	0.0415	0.2650	0.4282	0.043*
C4	0.2099 (3)	0.2226 (3)	0.1610 (3)	0.0397 (6)
H4A	0.1774	0.2663	0.0890	0.048*
H4B	0.1321	0.2479	0.2081	0.048*
C5	0.4628 (3)	0.4045 (3)	0.2123 (2)	0.0372 (6)
H5	0.4303	0.4445	0.1423	0.045*
C6	0.0157 (3)	−0.0051 (4)	0.2462 (2)	0.0444 (7)
H6A	−0.0454	0.0798	0.2214	0.053*
H6B	−0.0623	−0.0921	0.2393	0.053*
C7	0.2892 (3)	−0.0154 (4)	0.0350 (3)	0.0430 (7)
H7	0.3476	0.0535	0.0076	0.052*
C8	0.1177 (4)	−0.2205 (3)	0.1138 (3)	0.0466 (7)
H8	0.0601	−0.2909	0.1407	0.056*
C9	0.4618 (4)	0.2681 (4)	0.3476 (3)	0.0526 (8)
H9	0.4305	0.1979	0.3888	0.063*
C10	0.2212 (4)	−0.0315 (3)	0.4443 (3)	0.0493 (7)
H10	0.2497	−0.1322	0.4167	0.059*
C11	0.2777 (4)	0.0627 (3)	0.5594 (3)	0.0465 (7)
H11	0.3536	0.0377	0.6253	0.056*
C12	0.2873 (4)	−0.1759 (4)	−0.0095 (3)	0.0529 (8)
H12	0.3440	−0.2143	−0.0663	0.063*
C13	0.2020 (4)	−0.2781 (4)	0.0301 (3)	0.0536 (8)
H13	0.2008	−0.3864	0.0006	0.064*
C14	0.6028 (4)	0.3625 (4)	0.3844 (3)	0.0503 (8)
H14	0.6865	0.3682	0.4564	0.060*

	U11	U22	U33	U12	U13	U23
Zn1	0.03700 (18)	0.02838 (17)	0.02722 (17)	−0.00505 (12)	0.00577 (12)	0.00311 (12)
Cl1	0.0514 (4)	0.0511 (4)	0.0332 (4)	−0.0078 (3)	0.0000 (3)	0.0161 (3)
Cl2	0.0478 (4)	0.0450 (4)	0.0513 (4)	0.0128 (3)	0.0123 (3)	0.0126 (3)
N1	0.0403 (12)	0.0338 (12)	0.0311 (11)	−0.0096 (9)	0.0042 (9)	0.0056 (9)
N2	0.0405 (12)	0.0316 (11)	0.0282 (11)	0.0006 (9)	0.0081 (9)	0.0028 (9)
N3	0.0337 (11)	0.0323 (11)	0.0355 (12)	−0.0045 (9)	0.0059 (9)	0.0078 (9)
N4	0.0420 (12)	0.0327 (12)	0.0289 (11)	−0.0066 (9)	0.0111 (9)	0.0012 (9)
C1	0.0353 (13)	0.0378 (14)	0.0267 (12)	−0.0059 (11)	0.0060 (11)	−0.0004 (10)
C2	0.0315 (12)	0.0367 (14)	0.0289 (13)	0.0000 (11)	0.0036 (10)	0.0044 (11)
C3	0.0409 (14)	0.0315 (13)	0.0331 (14)	0.0015 (11)	0.0096 (11)	0.0041 (11)
C4	0.0315 (13)	0.0351 (14)	0.0472 (16)	−0.0006 (11)	0.0063 (12)	0.0057 (12)
C5	0.0425 (15)	0.0348 (14)	0.0312 (14)	−0.0041 (11)	0.0059 (11)	0.0079 (11)
C6	0.0414 (15)	0.0506 (17)	0.0320 (14)	−0.0166 (13)	0.0093 (12)	−0.0048 (12)
C7	0.0387 (14)	0.0509 (17)	0.0423 (16)	0.0027 (13)	0.0159 (12)	0.0119 (13)
C8	0.0583 (18)	0.0347 (15)	0.0396 (16)	−0.0110 (13)	0.0089 (14)	0.0028 (12)
C9	0.0502 (17)	0.0552 (19)	0.0521 (18)	−0.0132 (14)	0.0030 (14)	0.0290 (15)
C10	0.072 (2)	0.0315 (15)	0.0442 (17)	0.0105 (14)	0.0202 (15)	0.0037 (12)
C11	0.0595 (18)	0.0429 (16)	0.0372 (15)	0.0118 (14)	0.0102 (14)	0.0133 (13)
C12	0.0480 (17)	0.061 (2)	0.0457 (18)	0.0137 (15)	0.0163 (14)	0.0000 (15)
C13	0.065 (2)	0.0349 (16)	0.0481 (18)	0.0098 (14)	0.0053 (15)	−0.0028 (13)
C14	0.0486 (17)	0.0542 (19)	0.0399 (16)	−0.0125 (14)	−0.0049 (13)	0.0187 (14)

Zn1—N1	2.000 (2)	C3—H3	0.9300
Zn1—N2i	2.017 (2)	C4—H4A	0.9700
Zn1—Cl1	2.2309 (8)	C4—H4B	0.9700
Zn1—Cl2	2.2428 (8)	C5—H5	0.9300
N1—C5	1.320 (3)	C6—H6A	0.9700
N1—C14	1.366 (4)	C6—H6B	0.9700
N2—C3	1.317 (3)	C7—C12	1.379 (4)
N2—C11	1.371 (4)	C7—H7	0.9300
N2—Zn1i	2.017 (2)	C8—C13	1.377 (5)
N3—C5	1.330 (3)	C8—H8	0.9300
N3—C9	1.366 (4)	C9—C14	1.348 (4)
N3—C4	1.475 (3)	C9—H9	0.9300
N4—C3	1.332 (3)	C10—C11	1.350 (4)
N4—C10	1.365 (4)	C10—H10	0.9300
N4—C6	1.476 (3)	C11—H11	0.9300
C1—C2	1.392 (4)	C12—C13	1.363 (5)
C1—C8	1.395 (4)	C12—H12	0.9300
C1—C6	1.509 (4)	C13—H13	0.9300
C2—C7	1.383 (4)	C14—H14	0.9300
C2—C4	1.512 (4)
N1—Zn1—N2i	108.85 (9)	N1—C5—N3	111.4 (2)
N1—Zn1—Cl1	106.18 (7)	N1—C5—H5	124.3
N2i—Zn1—Cl1	108.10 (7)	N3—C5—H5	124.3
N1—Zn1—Cl2	112.82 (7)	N4—C6—C1	113.2 (2)
N2i—Zn1—Cl2	104.18 (7)	N4—C6—H6A	108.9
Cl1—Zn1—Cl2	116.46 (3)	C1—C6—H6A	108.9
C5—N1—C14	105.8 (2)	N4—C6—H6B	108.9
C5—N1—Zn1	123.62 (18)	C1—C6—H6B	108.9
C14—N1—Zn1	130.57 (18)	H6A—C6—H6B	107.7
C3—N2—C11	105.6 (2)	C12—C7—C2	121.4 (3)
C3—N2—Zn1i	123.80 (18)	C12—C7—H7	119.3
C11—N2—Zn1i	130.53 (19)	C2—C7—H7	119.3
C5—N3—C9	107.0 (2)	C13—C8—C1	121.1 (3)
C5—N3—C4	125.4 (2)	C13—C8—H8	119.4
C9—N3—C4	127.6 (2)	C1—C8—H8	119.4
C3—N4—C10	107.1 (2)	C14—C9—N3	106.7 (2)
C3—N4—C6	125.6 (2)	C14—C9—H9	126.6
C10—N4—C6	127.2 (2)	N3—C9—H9	126.6
C2—C1—C8	118.8 (2)	C11—C10—N4	106.5 (2)
C2—C1—C6	123.4 (2)	C11—C10—H10	126.7
C8—C1—C6	117.8 (3)	N4—C10—H10	126.7
C7—C2—C1	119.0 (2)	C10—C11—N2	109.2 (3)
C7—C2—C4	118.3 (2)	C10—C11—H11	125.4
C1—C2—C4	122.7 (2)	N2—C11—H11	125.4
N2—C3—N4	111.5 (2)	C13—C12—C7	119.8 (3)
N2—C3—H3	124.3	C13—C12—H12	120.1
N4—C3—H3	124.3	C7—C12—H12	120.1
N3—C4—C2	111.8 (2)	C12—C13—C8	119.9 (3)
N3—C4—H4A	109.3	C12—C13—H13	120.1
C2—C4—H4A	109.3	C8—C13—H13	120.1
N3—C4—H4B	109.3	C9—C14—N1	109.1 (3)
C2—C4—H4B	109.3	C9—C14—H14	125.4
H4A—C4—H4B	107.9	N1—C14—H14	125.4

Zn1—N1	2.000 (2)
Zn1—N2i	2.017 (2)
Zn1—Cl1	2.2309 (8)
Zn1—Cl2	2.2428 (8)

N1—Zn1—N2i	108.85 (9)
Cl1—Zn1—Cl2	116.46 (3)

Symmetry code: (i) .