Di-chlorido-bis-[1-(2,4,6-tri-methyl-phen-yl)-1H-imidazole-κN (3)]copper(II).

In the title complex, [CuCl2(C12H14N2)2], the Cu(2+) cation is situated on an inversion centre and is coordinated by two N atoms from symmetry-related 1-mesityl-1H-imidazole ligands and by two chloride anions in a slightly distorted square-planar geometry. In the organic ligand, the dihedral angle between the benzene ring of the mesityl moiety and the imidazole ring is 76.99 (18)°. Weak intra-molecular C-H⋯Cl hydrogen-bonding inter-actions consolidate the mol-ecular conformation.

Related literature

For related structures, see: Awwadi (2013 ▶); Jia et al. (2005 ▶). For the bioactivity of Cu complexes, see: Beaudoin et al. (2009 ▶); Deegana et al. (2007 ▶); Pettit & Ueda (1992 ▶). For the photochemistry of Cu complexes, see: Kuang et al. (2002 ▶); Raptopoulou et al. (1998 ▶); Teyssot et al. (2007 ▶).

Experimental

Crystal data

[CuCl2(C12H14N2)2]

M = 506.94

Monoclinic,

a = 7.1488 (6) Å

b = 19.7517 (18) Å

c = 8.5126 (7) Å

β = 92.674 (8)°

V = 1200.68 (18) Å3

Z = 2

Cu Kα radiation

μ = 3.47 mm−1

T = 298 K

0.44 × 0.32 × 0.05 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.311, T max = 0.846

5702 measured reflections

2114 independent reflections

1738 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 1.02

2114 reflections

145 parameters

H-atom parameters constrained

Δρmax = 1.16 e Å−3

Δρmin = −1.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAIn class="Chemical">NT; 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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813028821/wm2773sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028821/wm2773Isup2.hkl

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

[CuCl2(C12H14N2)2]	F(000) = 526
Mr = 506.94	Dx = 1.402 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 7467 reflections
a = 7.1488 (6) Å	θ = 2.2–27.0°
b = 19.7517 (18) Å	µ = 3.47 mm−1
c = 8.5126 (7) Å	T = 298 K
β = 92.674 (8)°	Plate, green
V = 1200.68 (18) Å3	0.44 × 0.32 × 0.05 mm
Z = 2

Bruker APEX CCD diffractometer	2114 independent reflections
Radiation source: fine-focus sealed tube	1738 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
phi and ω scans	θmax = 66.9°, θmin = 4.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→8
Tmin = 0.311, Tmax = 0.846	k = −21→23
5702 measured reflections	l = −10→9

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0792P)2 + 1.6476P] where P = (Fo2 + 2Fc2)/3
2114 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 1.16 e Å−3
0 restraints	Δρmin = −1.18 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
Cu1	0.5000	0.5000	0.5000	0.0301 (3)
Cl1	0.2765 (2)	0.45641 (8)	0.65130 (12)	0.0843 (6)
N1	0.3864 (4)	0.45022 (13)	0.3140 (3)	0.0271 (6)
N2	0.2163 (4)	0.37951 (14)	0.1669 (3)	0.0298 (6)
C5	−0.0735 (5)	0.33960 (18)	0.0315 (4)	0.0321 (7)
C7	−0.1896 (5)	0.28533 (19)	−0.0109 (4)	0.0370 (8)
H7	−0.2996	0.2937	−0.0704	0.044*
C4	0.0884 (4)	0.32493 (17)	0.1230 (4)	0.0292 (7)
C1	0.2452 (5)	0.40602 (17)	0.3112 (4)	0.0305 (7)
H1	0.1762	0.3950	0.3976	0.037*
C2	0.4488 (5)	0.45081 (18)	0.1632 (4)	0.0348 (8)
H2	0.5475	0.4769	0.1295	0.042*
C8	−0.1471 (5)	0.21907 (18)	0.0325 (4)	0.0358 (8)
C11	0.1388 (5)	0.25940 (17)	0.1680 (4)	0.0296 (7)
C10	0.0168 (5)	0.20712 (18)	0.1221 (4)	0.0345 (8)
H10	0.0461	0.1630	0.1525	0.041*
C12	0.3186 (5)	0.2443 (2)	0.2602 (4)	0.0399 (9)
H12A	0.3064	0.2570	0.3681	0.060*
H12B	0.4189	0.2695	0.2171	0.060*
H12C	0.3452	0.1968	0.2543	0.060*
C6	−0.1178 (5)	0.41059 (19)	−0.0233 (5)	0.0430 (9)
H6A	−0.1165	0.4405	0.0657	0.065*
H6B	−0.2395	0.4114	−0.0760	0.065*
H6C	−0.0256	0.4251	−0.0946	0.065*
C9	−0.2722 (6)	0.1608 (2)	−0.0181 (6)	0.0521 (10)
H9A	−0.2241	0.1196	0.0282	0.078*
H9B	−0.2757	0.1569	−0.1306	0.078*
H9C	−0.3965	0.1687	0.0160	0.078*
C3	0.3455 (5)	0.40795 (19)	0.0722 (4)	0.0372 (8)
H3	0.3590	0.3993	−0.0341	0.045*

	U11	U22	U33	U12	U13	U23
Cu1	0.0369 (4)	0.0328 (4)	0.0208 (4)	−0.0118 (3)	0.0032 (3)	−0.0030 (3)
Cl1	0.1018 (10)	0.1223 (12)	0.0307 (5)	−0.0855 (9)	0.0242 (5)	−0.0249 (6)
N1	0.0296 (14)	0.0288 (14)	0.0230 (13)	−0.0028 (11)	0.0024 (10)	−0.0001 (11)
N2	0.0329 (14)	0.0316 (15)	0.0252 (13)	−0.0094 (12)	0.0043 (11)	−0.0045 (11)
C5	0.0282 (16)	0.0331 (18)	0.0352 (17)	−0.0009 (14)	0.0049 (13)	−0.0074 (15)
C7	0.0271 (17)	0.042 (2)	0.042 (2)	−0.0025 (15)	−0.0027 (14)	−0.0063 (16)
C4	0.0296 (16)	0.0339 (17)	0.0242 (15)	−0.0089 (14)	0.0044 (12)	−0.0074 (14)
C1	0.0339 (17)	0.0350 (17)	0.0229 (15)	−0.0094 (14)	0.0042 (13)	−0.0035 (13)
C2	0.0401 (19)	0.0388 (19)	0.0259 (17)	−0.0128 (15)	0.0050 (14)	−0.0009 (14)
C8	0.0323 (18)	0.0363 (19)	0.0391 (19)	−0.0084 (15)	0.0041 (14)	−0.0085 (15)
C11	0.0331 (17)	0.0327 (18)	0.0234 (16)	−0.0054 (14)	0.0045 (13)	−0.0011 (13)
C10	0.0372 (19)	0.0314 (18)	0.0354 (18)	−0.0055 (15)	0.0057 (14)	−0.0022 (15)
C12	0.042 (2)	0.042 (2)	0.0352 (19)	−0.0074 (16)	−0.0045 (15)	0.0033 (16)
C6	0.038 (2)	0.036 (2)	0.055 (2)	0.0018 (16)	−0.0016 (17)	−0.0028 (17)
C9	0.042 (2)	0.043 (2)	0.071 (3)	−0.0121 (18)	−0.0017 (19)	−0.012 (2)
C3	0.045 (2)	0.046 (2)	0.0213 (16)	−0.0150 (17)	0.0087 (14)	−0.0058 (15)

Cu1—N1i	2.004 (3)	C6—H6A	0.9600
Cu1—N1	2.004 (3)	C6—H6B	0.9600
Cu1—Cl1i	2.2684 (10)	C6—H6C	0.9600
Cu1—Cl1	2.2684 (10)	C7—C8	1.390 (5)
N1—C1	1.334 (4)	C7—H7	0.9300
N1—C2	1.378 (4)	C8—C10	1.388 (5)
N2—C1	1.343 (4)	C8—C9	1.509 (5)
N2—C3	1.374 (4)	C9—H9A	0.9600
N2—C4	1.451 (4)	C9—H9B	0.9600
C1—H1	0.9300	C9—H9C	0.9600
C2—C3	1.345 (5)	C10—C11	1.396 (5)
C2—H2	0.9300	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.504 (5)
C4—C11	1.392 (5)	C12—H12A	0.9600
C4—C5	1.395 (5)	C12—H12B	0.9600
C5—C7	1.393 (5)	C12—H12C	0.9600
C5—C6	1.507 (5)
N1i—Cu1—N1	180.00 (13)	H6A—C6—H6B	109.5
N1i—Cu1—Cl1i	89.56 (8)	C5—C6—H6C	109.5
N1—Cu1—Cl1i	90.44 (8)	H6A—C6—H6C	109.5
N1i—Cu1—Cl1	90.44 (8)	H6B—C6—H6C	109.5
N1—Cu1—Cl1	89.56 (8)	C8—C7—C5	122.4 (3)
Cl1i—Cu1—Cl1	180.00 (7)	C8—C7—H7	118.8
C1—N1—C2	105.5 (3)	C5—C7—H7	118.8
C1—N1—Cu1	127.8 (2)	C10—C8—C7	118.3 (3)
C2—N1—Cu1	126.5 (2)	C10—C8—C9	120.1 (3)
C1—N2—C3	107.4 (3)	C7—C8—C9	121.6 (3)
C1—N2—C4	126.4 (3)	C8—C9—H9A	109.5
C3—N2—C4	125.8 (3)	C8—C9—H9B	109.5
N1—C1—N2	110.8 (3)	H9A—C9—H9B	109.5
N1—C1—H1	124.6	C8—C9—H9C	109.5
N2—C1—H1	124.6	H9A—C9—H9C	109.5
C3—C2—N1	109.8 (3)	H9B—C9—H9C	109.5
C3—C2—H2	125.1	C8—C10—C11	121.9 (3)
N1—C2—H2	125.1	C8—C10—H10	119.0
C2—C3—N2	106.6 (3)	C11—C10—H10	119.0
C2—C3—H3	126.7	C4—C11—C10	117.4 (3)
N2—C3—H3	126.7	C4—C11—C12	122.1 (3)
C11—C4—C5	123.0 (3)	C10—C11—C12	120.5 (3)
C11—C4—N2	117.9 (3)	C11—C12—H12A	109.5
C5—C4—N2	119.1 (3)	C11—C12—H12B	109.5
C7—C5—C4	117.0 (3)	H12A—C12—H12B	109.5
C7—C5—C6	121.4 (3)	C11—C12—H12C	109.5
C4—C5—C6	121.5 (3)	H12A—C12—H12C	109.5
C5—C6—H6A	109.5	H12B—C12—H12C	109.5
C5—C6—H6B	109.5
Cl1i—Cu1—N1—C1	174.6 (3)	C11—C4—C5—C7	1.9 (5)
Cl1—Cu1—N1—C1	−5.4 (3)	N2—C4—C5—C7	178.4 (3)
Cl1i—Cu1—N1—C2	0.1 (3)	C11—C4—C5—C6	−176.2 (3)
Cl1—Cu1—N1—C2	−179.9 (3)	N2—C4—C5—C6	0.3 (5)
C2—N1—C1—N2	−0.3 (4)	C4—C5—C7—C8	−1.1 (5)
Cu1—N1—C1—N2	−175.7 (2)	C6—C5—C7—C8	177.1 (4)
C3—N2—C1—N1	0.1 (4)	C5—C7—C8—C10	0.4 (5)
C4—N2—C1—N1	173.2 (3)	C5—C7—C8—C9	−178.4 (4)
C1—N1—C2—C3	0.4 (4)	C7—C8—C10—C11	−0.5 (5)
Cu1—N1—C2—C3	175.9 (2)	C9—C8—C10—C11	178.3 (3)
N1—C2—C3—N2	−0.3 (4)	C5—C4—C11—C10	−2.0 (5)
C1—N2—C3—C2	0.1 (4)	N2—C4—C11—C10	−178.6 (3)
C4—N2—C3—C2	−173.0 (3)	C5—C4—C11—C12	177.0 (3)
C1—N2—C4—C11	−74.2 (4)	N2—C4—C11—C12	0.4 (5)
C3—N2—C4—C11	97.6 (4)	C8—C10—C11—C4	1.2 (5)
C1—N2—C4—C5	109.1 (4)	C8—C10—C11—C12	−177.8 (3)
C3—N2—C4—C5	−79.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.93	2.55	3.060 (4)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl1	0.93	2.55	3.060 (4)	115