A second monoclinic polymorph of di-μ-chlorido-bis­(chlorido{2-[(4-ethyl­phen­yl)imino­meth­yl]pyridine-κ2N,N′}copper(II))

Khalaj, M.; Dehghanpour, S.; Mahmoudi, A.; Khalaj, A.; Lough, A.J.

doi:10.1107/S1600536812026347

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m920-m921

https://doi.org/10.1107/S1600536812026347

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A second monoclinic polymorph of di-μ-chlorido-bis(chlorido{2-[(4-ethylphenyl)iminomethyl]pyridine-κ²N,N′}copper(II))

Mehdi Khalaj,^a ^* Saeed Dehghanpour,^b Ali Mahmoudi,^c Arash Khalaj ^c and Alan J. Lough ^d

^aDepartment of Chemistry, Islamic Azad University, Buinzahra Branch, Qazvin, Iran, ^bDepartment of Chemistry, Alzahra University, Tehran, Iran, ^cDepartment of Chemistry, Islamic Azad University, Karaj Branch, Karaj, Iran, and ^dDepartment of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, Canada M5S 3H6
^*Correspondence e-mail: khalaj_mehdi@yahoo.com

(Received 8 May 2012; accepted 11 June 2012; online 16 June 2012)

The title compound, [Cu₂Cl₄(C₁₄H₁₄N₂)₂], is a new polymorph of a previously reported compound [Dehghanpour et al. (2011 ). Acta Cryst. E67, m1296]. The current polymorph was obtained from an acetonitrile solution of the title compound. Like the first polymorph, it is monoclinic (space group P2₁/c). The unique Cu^II ion in the title centrosymmetric dinuclear complex is in a distorted trigonal–bipyramidal coordination environment formed by the bis-chelating N-heterocyclic ligand, two bridging Cl ligands and one terminal Cl ligand. In the crystal, weak C—H⋯Cl hydrogen bonds are observed in addition to π–π stacking interactions, with a centroid–centroid distance of 3.6597 (18) Å.

Related literature

For the synthesis of the ligand, see: Dehghanpour et al. (2009 ). For background to diimine complexes and related structures, see: Dehghanpour et al. (2011); Salehzadeh et al. (2011 ). For an index of trigonality as a general descriptor of five-coordinate complexes, see: Addison et al. (1984 ).

Experimental

Crystal data

[Cu₂Cl₄(C₁₄H₁₄N₂)₂]
M_r = 689.42
Monoclinic, P 2₁ /c
a = 7.8480 (4) Å
b = 13.7160 (6) Å
c = 14.4601 (7) Å
β = 113.924 (3)°
V = 1422.80 (12) Å³
Z = 2
Mo Kα radiation
μ = 1.90 mm⁻¹
T = 150 K
0.30 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.581, T_max = 0.689
7862 measured reflections
3249 independent reflections
2399 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 1.05
3249 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cl1	0.95	2.80	3.364 (3)	119
C2—H2A⋯Cl2ⁱ	0.95	2.76	3.445 (3)	130
C6—H6A⋯Cl2ⁱⁱ	0.95	2.62	3.506 (3)	155
C12—H12A⋯Cl2	0.95	2.80	3.450 (3)	126
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812026347/fb2253sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026347/fb2253Isup2.hkl

checkCIF report

Comment top

The crystal structure of a polymorph of the title compound has previously been reported (Dehghanpour et al., 2011). In the course of our studies on the synthesis, structural and spectroscopic characterization of transition metal complexes with diimine ligands (Dehghanpour et al., 2009; Salehzadeh et al., 2011) a new polymorph of the title compound was obtained.

The title complex is shown in Fig. 1. The most significant structural difference between this structure and the polymorph (Dehghanpour et al., 2011) is the coordination environment of the Cu^II ion. The structural index τ, (Addison et al., 1984) which is a measure of trigonal distortion, is 0.75 for the title structure indicating a distorted trigonal-bipyramidal environment of Cu(II) for the title compound. The value of τ is 0.21 for the other polymorph with a distorted square-planar coordination enviroment. These differences are shown in Fig. 2.

The interplanar angles between the benzene and pyridine rings in the title structure is 12.40 (15)° whereas this angle is 43.02 (13)° in the polymorph determined by Dehghanpour et al. (2011).

In the crystal, weak C—H···Cl hydrogen bonds are observed in addition to π–π stacking interactions with a centroid to centroid distance of 3.6597 (18)Å for Cg1···Cg2ⁱ (where Cg1 and Cg2 are centroids of the N1-C1-C5 and C7-C12 rings; symmetry code: 1+x, y, z).

Related literature top

For the synthesis of the ligand, see: Dehghanpour et al. (2009). For background to diimine complexes and related structures, see: Dehghanpour et al. (2011); Salehzadeh et al. (2011). For an index of trigonality as a general descriptor of five-coordinate complexes, see: Addison et al. (1984).

Experimental top

The title complex was prepared by the reaction of CuCl₂ (13.4 mg, 0.1 mmol) and (4-methylphenyl)pyridin-2-ylmethyleneamine (21.0 mg, 0.1) in 15 ml of acetonitrile at room temperature. The solution was allowed to stand at room temperature and orange block-shaped crystal of the title compound suitable for X-ray analysis precipitated within few days.

Structure description top

The interplanar angles between the benzene and pyridine rings in the title structure is 12.40 (15)° whereas this angle is 43.02 (13)° in the polymorph determined by Dehghanpour et al. (2011).

For the synthesis of the ligand, see: Dehghanpour et al. (2009). For background to diimine complexes and related structures, see: Dehghanpour et al. (2011); Salehzadeh et al. (2011). For an index of trigonality as a general descriptor of five-coordinate complexes, see: Addison et al. (1984).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the structure of the title complex, with displacement ellipsoids drawn at the 50% probability level [H atoms are represented as spheres of arbitrary radius]. Unlabelled atoms are related by the symmetry operator (-x+1, -y+1, -z+1).
	Fig. 2. A comparison of both polymorphs. The title molecule is shown in red while that determined by Dehghanpour et al. (2011) in green (Mercury; Macrae et al., 2006).

di-µ-chlorido-bis(chlorido{2-[(4-ethylphenyl)iminomethyl]pyridine- κ²N,N'}copper(II)) top

Crystal data top

[Cu₂Cl₄(C₁₄H₁₄N₂)₂]	F(000) = 700
M_r = 689.42	D_x = 1.609 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4440 reflections
a = 7.8480 (4) Å	θ = 2.6–27.5°
b = 13.7160 (6) Å	µ = 1.90 mm⁻¹
c = 14.4601 (7) Å	T = 150 K
β = 113.924 (3)°	Block, orange
V = 1422.80 (12) Å³	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	3249 independent reflections
Radiation source: fine-focus sealed tube	2399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.8°
φ scans and ω scans with κ offsets	h = −10→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −17→15
T_min = 0.581, T_max = 0.689	l = −12→18
7862 measured reflections

Refinement top

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0441P)² + 0.8729P] where P = (F_o² + 2F_c²)/3
3249 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³
55 constraints

Crystal data top

[Cu₂Cl₄(C₁₄H₁₄N₂)₂]	V = 1422.80 (12) Å³
M_r = 689.42	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8480 (4) Å	µ = 1.90 mm⁻¹
b = 13.7160 (6) Å	T = 150 K
c = 14.4601 (7) Å	0.30 × 0.25 × 0.20 mm
β = 113.924 (3)°

Data collection top

Nonius KappaCCD diffractometer	3249 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	2399 reflections with I > 2σ(I)
T_min = 0.581, T_max = 0.689	R_int = 0.045
7862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.05	Δρ_max = 0.76 e Å⁻³
3249 reflections	Δρ_min = −0.70 e Å⁻³
173 parameters

Special details top

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.50129 (5)	0.45502 (2)	0.61249 (3)	0.02458 (13)
Cl1	0.60970 (11)	0.59376 (5)	0.56397 (5)	0.0301 (2)
Cl2	0.33826 (11)	0.53968 (5)	0.68632 (6)	0.03089 (19)
N1	0.7670 (3)	0.40393 (17)	0.70183 (18)	0.0239 (5)
N2	0.4320 (3)	0.32164 (16)	0.64881 (17)	0.0227 (5)
C1	0.9333 (4)	0.4446 (2)	0.7264 (2)	0.0290 (7)
H1A	0.9403	0.5066	0.6987	0.035*
C2	1.0974 (4)	0.4000 (2)	0.7912 (2)	0.0329 (7)
H2A	1.2139	0.4315	0.8077	0.040*
C3	1.0897 (4)	0.3100 (2)	0.8311 (2)	0.0337 (7)
H3A	1.2003	0.2784	0.8757	0.040*
C4	0.9176 (4)	0.2662 (2)	0.8049 (2)	0.0342 (7)
H4A	0.9079	0.2034	0.8301	0.041*
C5	0.7598 (4)	0.3157 (2)	0.7415 (2)	0.0265 (6)
C6	0.5738 (4)	0.2752 (2)	0.7108 (2)	0.0287 (7)
H6A	0.5573	0.2140	0.7368	0.034*
C7	0.2496 (4)	0.2788 (2)	0.6146 (2)	0.0262 (6)
C8	0.2256 (5)	0.1806 (2)	0.6308 (3)	0.0442 (9)
H8A	0.3310	0.1398	0.6634	0.053*
C9	0.0487 (5)	0.1429 (3)	0.5996 (3)	0.0530 (11)
H9A	0.0340	0.0758	0.6111	0.064*
C10	−0.1092 (4)	0.1998 (2)	0.5515 (3)	0.0368 (8)
C11	−0.0829 (4)	0.2962 (2)	0.5328 (2)	0.0302 (7)
H11A	−0.1883	0.3364	0.4983	0.036*
C12	0.0946 (4)	0.3355 (2)	0.5634 (2)	0.0279 (7)
H12A	0.1094	0.4018	0.5491	0.033*
C13	−0.3033 (5)	0.1564 (3)	0.5204 (3)	0.0522 (10)
H13A	−0.3205	0.1371	0.5821	0.063*
H13B	−0.3971	0.2072	0.4854	0.063*
C14	−0.3384 (6)	0.0684 (3)	0.4514 (3)	0.0581 (11)
H14A	−0.4675	0.0465	0.4307	0.087*
H14B	−0.2532	0.0156	0.4876	0.087*
H14C	−0.3170	0.0862	0.3913	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0276 (2)	0.01543 (19)	0.0310 (2)	−0.00135 (14)	0.01221 (17)	0.00164 (14)
Cl1	0.0399 (4)	0.0189 (4)	0.0290 (4)	−0.0081 (3)	0.0116 (3)	0.0005 (3)
Cl2	0.0375 (4)	0.0188 (4)	0.0416 (4)	−0.0010 (3)	0.0214 (4)	−0.0044 (3)
N1	0.0276 (13)	0.0190 (12)	0.0258 (13)	−0.0006 (11)	0.0116 (11)	0.0015 (10)
N2	0.0259 (13)	0.0171 (12)	0.0258 (13)	−0.0004 (10)	0.0113 (10)	−0.0018 (10)
C1	0.0290 (16)	0.0277 (16)	0.0307 (17)	−0.0014 (13)	0.0127 (14)	0.0044 (13)
C2	0.0263 (16)	0.0390 (18)	0.0329 (18)	−0.0026 (15)	0.0114 (14)	0.0017 (14)
C3	0.0287 (17)	0.0326 (17)	0.0346 (18)	0.0042 (14)	0.0074 (14)	0.0065 (14)
C4	0.0360 (18)	0.0232 (15)	0.0378 (18)	0.0020 (15)	0.0094 (15)	0.0050 (14)
C5	0.0298 (16)	0.0205 (14)	0.0299 (16)	0.0022 (13)	0.0127 (13)	0.0014 (12)
C6	0.0322 (17)	0.0186 (14)	0.0345 (17)	0.0005 (13)	0.0127 (14)	0.0043 (13)
C7	0.0268 (15)	0.0233 (15)	0.0298 (16)	−0.0013 (13)	0.0126 (13)	0.0006 (12)
C8	0.0275 (18)	0.0250 (17)	0.069 (3)	0.0008 (15)	0.0081 (17)	0.0166 (17)
C9	0.0330 (19)	0.0299 (19)	0.082 (3)	−0.0036 (16)	0.009 (2)	0.0176 (19)
C10	0.0278 (17)	0.0346 (19)	0.047 (2)	−0.0026 (15)	0.0136 (15)	0.0002 (15)
C11	0.0265 (16)	0.0283 (16)	0.0328 (17)	0.0048 (13)	0.0090 (14)	−0.0013 (13)
C12	0.0300 (16)	0.0193 (14)	0.0317 (17)	0.0016 (13)	0.0097 (13)	0.0000 (12)
C13	0.033 (2)	0.042 (2)	0.076 (3)	−0.0026 (17)	0.0158 (19)	0.004 (2)
C14	0.048 (2)	0.072 (3)	0.048 (2)	−0.023 (2)	0.0130 (19)	−0.003 (2)

Geometric parameters (Å, º) top

Cu1—N2	2.037 (2)	C6—H6A	0.9500
Cu1—N1	2.079 (2)	C7—C12	1.379 (4)
Cu1—Cl2	2.2876 (8)	C7—C8	1.393 (4)
Cu1—Cl1	2.3067 (8)	C8—C9	1.375 (5)
Cu1—Cl1ⁱ	2.4321 (8)	C8—H8A	0.9500
Cl1—Cu1ⁱ	2.4321 (8)	C9—C10	1.389 (5)
N1—C1	1.328 (4)	C9—H9A	0.9500
N1—C5	1.350 (4)	C10—C11	1.382 (4)
N2—C6	1.280 (4)	C10—C13	1.523 (5)
N2—C7	1.437 (4)	C11—C12	1.388 (4)
C1—C2	1.390 (4)	C11—H11A	0.9500
C1—H1A	0.9500	C12—H12A	0.9500
C2—C3	1.374 (4)	C13—C14	1.520 (6)
C2—H2A	0.9500	C13—H13A	0.9900
C3—C4	1.384 (4)	C13—H13B	0.9900
C3—H3A	0.9500	C14—H14A	0.9800
C4—C5	1.383 (4)	C14—H14B	0.9800
C4—H4A	0.9500	C14—H14C	0.9800
C5—C6	1.453 (4)

N2—Cu1—N1	80.94 (9)	N2—C6—H6A	119.9
N2—Cu1—Cl2	94.43 (7)	C5—C6—H6A	119.9
N1—Cu1—Cl2	119.40 (7)	C12—C7—C8	119.1 (3)
N2—Cu1—Cl1	171.55 (7)	C12—C7—N2	119.5 (3)
N1—Cu1—Cl1	93.80 (7)	C8—C7—N2	121.4 (3)
Cl2—Cu1—Cl1	93.91 (3)	C9—C8—C7	119.7 (3)
N2—Cu1—Cl1ⁱ	90.23 (7)	C9—C8—H8A	120.1
N1—Cu1—Cl1ⁱ	113.66 (7)	C7—C8—H8A	120.1
Cl2—Cu1—Cl1ⁱ	126.81 (3)	C8—C9—C10	122.0 (3)
Cl1—Cu1—Cl1ⁱ	85.82 (3)	C8—C9—H9A	119.0
Cu1—Cl1—Cu1ⁱ	94.18 (3)	C10—C9—H9A	119.0
C1—N1—C5	118.0 (3)	C11—C10—C9	117.5 (3)
C1—N1—Cu1	130.8 (2)	C11—C10—C13	121.8 (3)
C5—N1—Cu1	111.22 (19)	C9—C10—C13	120.7 (3)
C6—N2—C7	119.9 (2)	C10—C11—C12	121.3 (3)
C6—N2—Cu1	112.36 (19)	C10—C11—H11A	119.3
C7—N2—Cu1	127.69 (18)	C12—C11—H11A	119.3
N1—C1—C2	122.4 (3)	C7—C12—C11	120.3 (3)
N1—C1—H1A	118.8	C7—C12—H12A	119.9
C2—C1—H1A	118.8	C11—C12—H12A	119.9
C3—C2—C1	119.5 (3)	C14—C13—C10	113.4 (3)
C3—C2—H2A	120.3	C14—C13—H13A	108.9
C1—C2—H2A	120.3	C10—C13—H13A	108.9
C2—C3—C4	118.6 (3)	C14—C13—H13B	108.9
C2—C3—H3A	120.7	C10—C13—H13B	108.9
C4—C3—H3A	120.7	H13A—C13—H13B	107.7
C5—C4—C3	118.7 (3)	C13—C14—H14A	109.5
C5—C4—H4A	120.7	C13—C14—H14B	109.5
C3—C4—H4A	120.7	H14A—C14—H14B	109.5
N1—C5—C4	122.8 (3)	C13—C14—H14C	109.5
N1—C5—C6	115.0 (3)	H14A—C14—H14C	109.5
C4—C5—C6	122.2 (3)	H14B—C14—H14C	109.5
N2—C6—C5	120.3 (3)

N2—Cu1—Cl1—Cu1ⁱ	62.3 (5)	Cu1—N1—C5—C4	−179.1 (2)
N1—Cu1—Cl1—Cu1ⁱ	113.48 (7)	C1—N1—C5—C6	−179.5 (3)
Cl2—Cu1—Cl1—Cu1ⁱ	−126.67 (3)	Cu1—N1—C5—C6	2.2 (3)
Cl1ⁱ—Cu1—Cl1—Cu1ⁱ	0.0	C3—C4—C5—N1	1.7 (5)
N2—Cu1—N1—C1	178.7 (3)	C3—C4—C5—C6	−179.7 (3)
Cl2—Cu1—N1—C1	−91.4 (3)	C7—N2—C6—C5	176.6 (3)
Cl1—Cu1—N1—C1	5.3 (3)	Cu1—N2—C6—C5	−4.4 (4)
Cl1ⁱ—Cu1—N1—C1	92.4 (3)	N1—C5—C6—N2	1.5 (4)
N2—Cu1—N1—C5	−3.39 (19)	C4—C5—C6—N2	−177.3 (3)
Cl2—Cu1—N1—C5	86.6 (2)	C6—N2—C7—C12	168.0 (3)
Cl1—Cu1—N1—C5	−176.73 (19)	Cu1—N2—C7—C12	−10.8 (4)
Cl1ⁱ—Cu1—N1—C5	−89.63 (19)	C6—N2—C7—C8	−12.8 (4)
N1—Cu1—N2—C6	4.2 (2)	Cu1—N2—C7—C8	168.4 (3)
Cl2—Cu1—N2—C6	−114.9 (2)	C12—C7—C8—C9	−2.7 (5)
Cl1—Cu1—N2—C6	56.1 (6)	N2—C7—C8—C9	178.1 (3)
Cl1ⁱ—Cu1—N2—C6	118.1 (2)	C7—C8—C9—C10	0.1 (6)
N1—Cu1—N2—C7	−176.9 (2)	C8—C9—C10—C11	2.1 (6)
Cl2—Cu1—N2—C7	64.0 (2)	C8—C9—C10—C13	−178.3 (4)
Cl1—Cu1—N2—C7	−125.0 (4)	C9—C10—C11—C12	−1.8 (5)
Cl1ⁱ—Cu1—N2—C7	−63.0 (2)	C13—C10—C11—C12	178.6 (3)
C5—N1—C1—C2	−0.4 (4)	C8—C7—C12—C11	2.9 (5)
Cu1—N1—C1—C2	177.5 (2)	N2—C7—C12—C11	−177.8 (3)
N1—C1—C2—C3	0.6 (5)	C10—C11—C12—C7	−0.7 (5)
C1—C2—C3—C4	0.3 (5)	C11—C10—C13—C14	123.0 (4)
C2—C3—C4—C5	−1.4 (5)	C9—C10—C13—C14	−56.6 (5)
C1—N1—C5—C4	−0.8 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl1	0.95	2.80	3.364 (3)	119
C2—H2A···Cl2ⁱⁱ	0.95	2.76	3.445 (3)	130
C6—H6A···Cl2ⁱⁱⁱ	0.95	2.62	3.506 (3)	155
C12—H12A···Cl2	0.95	2.80	3.450 (3)	126

Symmetry codes: (ii) x+1, y, z; (iii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Cu₂Cl₄(C₁₄H₁₄N₂)₂]
M_r	689.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	7.8480 (4), 13.7160 (6), 14.4601 (7)
β (°)	113.924 (3)
V (Å³)	1422.80 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.90
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.581, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections	7862, 3249, 2399
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 1.05
No. of reflections	3249
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.70

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl1	0.95	2.80	3.364 (3)	119
C2—H2A···Cl2ⁱ	0.95	2.76	3.445 (3)	130
C6—H6A···Cl2ⁱⁱ	0.95	2.62	3.506 (3)	155
C12—H12A···Cl2	0.95	2.80	3.450 (3)	126.

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+3/2.

Acknowledgements

The authors would like to acknowledge the Islamic Azad and Alzahra University Research Councils for partial support of this work.

References

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