Bis[μ-3-ethyl-4-phenyl-5-(2-pyrid­yl)-4H-1,2,4-triazole]bis­[dichloridocopper(II)]

Wang, Z.; Liu, C.; Zhang, X.; Gong, X.

doi:10.1107/S160053680804035X

Bis[μ-3-ethyl-4-phenyl-5-(2-pyridyl)-4H-1,2,4-triazole]bis[dichloridocopper(II)]

The asymmetric unit of the title compound, [Cu₂Cl₄(C₁₅H₁₄N₄)₂], contains two halves of two centrosymmetric dinuclear molecules, A and B. The conformations of the two crystallographically independent molecules are slightly different: in A, the Cu

Cu separation is 4.174 (9) Å and the dihedral angle between the triazole and phenyl rings is 74.23 (11)°; these values are 4.137 (9) Å and 68.58 (13)°, respectively, in B. In each molecule, the copper(II) ions have a distorted trigonal–bipyramidal coordination geometry with a CuCl₂NN′N′′ chromophore. The crystal packing exhibits weak intermolecular C—H

Cl interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680804035X/cv2472sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680804035X/cv2472Isup2.hkl Contains datablock I

CCDC reference: 717967

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.006 Å
R factor = 0.044
wR factor = 0.069
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   273.000
            Value of melting point given =     0.000
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT234_ALERT_4_C Large Hirshfeld Difference C11    --  C12     ..       0.10  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C28    --  C29     ..       0.11  Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        273 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        273 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

As the 1,2,4-triazole ring posesses strong electron donors and coordination capability to transition metal ions, the coordination chemistry of 1,2,4-triazole derivatives has gained great attention in recent years (Klingele et al., 2005; Chen et al., 2008; Matsukizono et al., 2008). Some complexes of 1,2,4-triazoles with iron(II) have spin-crossover properties, which can be used as molecular-based memory devices, displays and optical switches (Kahn & Martinez, 1998; Moliner et al., 2001; Matouzenko et al., 2004). We report here the crystal structure analysis of the title compound, (I) (Fig. 1).

The asymmetric unit of the title compound contains two halves of two centrosymmetric dinuclear molecules, A and B, respectively. In A, the dihedral angle between the triazole and pyridine rings is 11.21 (16)°, and that between the triazole and benzene rings is 74.22 (11)°; those values in B are 9.02 (16)° and 68.58 (13)°, respectively.

The crystal packing exhibits weak intermolecular C—H···Cl interactions (Table 1).

Related literature top

For the magnetic and spin-crossover properties of 1,2,4-triazole complexes, see: Kahn & Martinez (1998); Klingele et al. (2005); Matouzenko et al. (2004); Moliner et al. (2001); For the fluorescent properties of 1,2,4-triazole complexes, see: Chen et al. (2008); Matsukizono et al. (2008).

Experimental top

The title compound was prepared by reaction of 3-ethyl-4-phenyl-5-(2-pyridyl)-1,2,4-triazole with copper(II) chloride in ethanol and water. To a warm solution of 0.501 grams of 3-ethyl-4-phenyl-5-(2-pyridyl)-1,2,4-triazole (2.0 mmol) in 10 ml e thanol, 0.682 grams of copper(II) chloride dihydrate (4.0 mmol) in 10 ml water was added. The filtrate was left to stand at room temperature for several days, and single crystals suitable for X-ray diffraction were collected.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of (I) with the atomic labelling and 30% probability displacement ellipsoids [symmetry codes: (i) -x + 1,-y + 2,-z; (ii) -x,-y + 1,-z + 1.

Bis[µ-3-ethyl-4-phenyl-5-(2-pyridyl)-4H-1,2,4- triazole]bis[dichloridocopper(II)] top

Crystal data top

[Cu₂Cl₄(C₁₅H₁₄N₄)₂]	Z = 2
M_r = 769.48	F(000) = 780
Triclinic, P1	D_x = 1.541 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3395 (11) Å	Cell parameters from 2456 reflections
b = 12.8096 (14) Å	θ = 2.2–24.2°
c = 13.9234 (16) Å	µ = 1.64 mm⁻¹
α = 92.533 (2)°	T = 273 K
β = 94.596 (2)°	Block, green
γ = 90.452 (2)°	0.30 × 0.26 × 0.24 mm
V = 1658.6 (3) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5716 independent reflections
Radiation source: sealed tube	4065 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→11
T_min = 0.62, T_max = 0.68	k = −15→10
8289 measured reflections	l = −16→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.01P)²] where P = (F_o² + 2F_c²)/3
5716 reflections	(Δ/σ)_max = 0.004
399 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Cu₂Cl₄(C₁₅H₁₄N₄)₂]	γ = 90.452 (2)°
M_r = 769.48	V = 1658.6 (3) Å³
Triclinic, P1	Z = 2
a = 9.3395 (11) Å	Mo Kα radiation
b = 12.8096 (14) Å	µ = 1.64 mm⁻¹
c = 13.9234 (16) Å	T = 273 K
α = 92.533 (2)°	0.30 × 0.26 × 0.24 mm
β = 94.596 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5716 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4065 reflections with I > 2σ(I)
T_min = 0.62, T_max = 0.68	R_int = 0.032
8289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.05	Δρ_max = 0.55 e Å⁻³
5716 reflections	Δρ_min = −0.40 e Å⁻³
399 parameters

Special details top

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.61708 (5)	0.91845 (3)	−0.09989 (3)	0.04319 (14)
Cu2	0.14043 (5)	0.57176 (3)	0.60559 (3)	0.04375 (14)
Cl1	0.52503 (13)	0.75357 (7)	−0.12247 (7)	0.0706 (4)
Cl2	0.71352 (11)	1.02338 (8)	−0.20518 (8)	0.0645 (3)
Cl3	0.05265 (12)	0.73248 (7)	0.64432 (7)	0.0655 (3)
Cl4	0.25757 (11)	0.44618 (8)	0.68906 (8)	0.0663 (3)
N1	0.8159 (3)	0.8654 (2)	−0.0588 (2)	0.0443 (8)
N2	0.6455 (3)	0.9681 (2)	0.05218 (19)	0.0379 (7)
N3	0.5746 (3)	1.0170 (2)	0.1247 (2)	0.0402 (8)
N4	0.7742 (3)	0.9542 (2)	0.1897 (2)	0.0377 (7)
N5	0.3290 (3)	0.6315 (2)	0.5707 (2)	0.0428 (8)
N6	0.1338 (3)	0.5377 (2)	0.45041 (19)	0.0381 (7)
N7	0.0455 (3)	0.4958 (2)	0.3749 (2)	0.0388 (8)
N8	0.2338 (3)	0.5611 (2)	0.3164 (2)	0.0401 (8)
C1	0.9021 (5)	0.8246 (3)	−0.1216 (3)	0.0562 (11)
H1	0.8662	0.8134	−0.1855	0.067*
C2	1.0420 (4)	0.7983 (3)	−0.0963 (3)	0.0551 (11)
H2	1.0988	0.7685	−0.1419	0.066*
C3	1.0958 (4)	0.8167 (3)	−0.0029 (3)	0.0557 (11)
H3	1.1909	0.8014	0.0159	0.067*
C4	1.0069 (4)	0.8582 (3)	0.0633 (3)	0.0500 (10)
H4	1.0406	0.8702	0.1276	0.060*
C5	0.8689 (4)	0.8814 (3)	0.0330 (3)	0.0384 (9)
C6	0.7641 (4)	0.9318 (2)	0.0928 (3)	0.0369 (9)
C7	0.6528 (4)	1.0085 (3)	0.2065 (3)	0.0394 (9)
C8	0.6207 (4)	1.0541 (3)	0.3019 (2)	0.0553 (11)
H8A	0.5369	1.0980	0.2930	0.066*
H8B	0.7007	1.0988	0.3268	0.066*
C9	0.5929 (5)	0.9754 (4)	0.3773 (3)	0.0924 (16)
H9A	0.5175	0.9280	0.3523	0.139*
H9B	0.5649	1.0117	0.4345	0.139*
H9C	0.6789	0.9370	0.3926	0.139*
C10	0.8771 (4)	0.9203 (3)	0.2639 (2)	0.0389 (9)
C11	0.8735 (4)	0.8180 (3)	0.2893 (3)	0.0533 (11)
H11	0.8095	0.7703	0.2565	0.064*
C12	0.9657 (5)	0.7877 (3)	0.3639 (3)	0.0658 (13)
H12	0.9645	0.7186	0.3816	0.079*
C13	1.0597 (5)	0.8572 (4)	0.4129 (3)	0.0666 (13)
H13	1.1212	0.8355	0.4639	0.080*
C14	1.0629 (4)	0.9590 (4)	0.3866 (3)	0.0593 (12)
H14	1.1270	1.0064	0.4196	0.071*
C15	0.9716 (4)	0.9910 (3)	0.3117 (3)	0.0464 (10)
H15	0.9737	1.0600	0.2936	0.056*
C16	0.4266 (4)	0.6705 (3)	0.6369 (3)	0.0557 (11)
H16	0.4034	0.6773	0.7006	0.067*
C17	0.5618 (5)	0.7017 (3)	0.6151 (3)	0.0618 (12)
H17	0.6275	0.7301	0.6630	0.074*
C18	0.5970 (5)	0.6905 (3)	0.5229 (3)	0.0628 (12)
H18	0.6884	0.7088	0.5070	0.075*
C19	0.4956 (4)	0.6514 (3)	0.4526 (3)	0.0579 (12)
H19	0.5170	0.6445	0.3885	0.069*
C20	0.3628 (4)	0.6231 (3)	0.4788 (3)	0.0423 (10)
C21	0.2472 (4)	0.5760 (2)	0.4143 (2)	0.0383 (9)
C22	0.1065 (4)	0.5101 (3)	0.2944 (3)	0.0407 (10)
C23	0.0445 (4)	0.4789 (3)	0.1960 (3)	0.0544 (11)
H23A	−0.0399	0.4355	0.2013	0.065*
H23B	0.1139	0.4367	0.1642	0.065*
C24	0.0022 (5)	0.5691 (3)	0.1334 (3)	0.0805 (15)
H24A	−0.0659	0.6120	0.1644	0.121*
H24B	−0.0403	0.5424	0.0720	0.121*
H24C	0.0860	0.6101	0.1239	0.121*
C25	0.3299 (4)	0.5928 (3)	0.2453 (2)	0.0425 (10)
C26	0.3472 (4)	0.6965 (3)	0.2290 (3)	0.0548 (11)
H26	0.3004	0.7474	0.2641	0.066*
C27	0.4356 (5)	0.7235 (3)	0.1596 (3)	0.0691 (13)
H27	0.4487	0.7934	0.1469	0.083*
C28	0.5050 (5)	0.6471 (4)	0.1087 (3)	0.0734 (14)
H28	0.5646	0.6659	0.0617	0.088*
C29	0.4870 (5)	0.5437 (4)	0.1266 (3)	0.0655 (13)
H29	0.5344	0.4927	0.0921	0.079*
C30	0.3985 (4)	0.5157 (3)	0.1956 (3)	0.0522 (11)
H30	0.3854	0.4458	0.2085	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0498 (3)	0.0414 (3)	0.0382 (3)	0.0052 (2)	0.0051 (2)	−0.0032 (2)
Cu2	0.0533 (3)	0.0406 (3)	0.0373 (3)	−0.0008 (2)	0.0068 (2)	−0.0036 (2)
Cl1	0.1114 (10)	0.0409 (6)	0.0567 (7)	−0.0113 (6)	−0.0079 (7)	−0.0003 (5)
Cl2	0.0555 (7)	0.0697 (7)	0.0714 (8)	−0.0007 (6)	0.0146 (6)	0.0207 (6)
Cl3	0.0942 (9)	0.0391 (6)	0.0654 (8)	0.0070 (6)	0.0238 (7)	−0.0036 (5)
Cl4	0.0598 (7)	0.0617 (7)	0.0785 (8)	0.0086 (6)	0.0030 (6)	0.0178 (6)
N1	0.049 (2)	0.0439 (19)	0.040 (2)	0.0092 (15)	0.0050 (17)	−0.0072 (16)
N2	0.043 (2)	0.0409 (19)	0.0296 (18)	0.0014 (15)	0.0044 (16)	−0.0041 (14)
N3	0.045 (2)	0.0405 (19)	0.0354 (19)	−0.0031 (15)	0.0071 (16)	−0.0055 (15)
N4	0.042 (2)	0.0347 (18)	0.0361 (19)	0.0014 (15)	0.0034 (16)	−0.0010 (14)
N5	0.047 (2)	0.0438 (19)	0.0367 (19)	−0.0040 (15)	0.0073 (17)	−0.0075 (15)
N6	0.045 (2)	0.0377 (18)	0.0317 (18)	0.0015 (15)	0.0046 (16)	−0.0018 (14)
N7	0.045 (2)	0.0374 (18)	0.0343 (18)	−0.0021 (14)	0.0062 (16)	−0.0055 (15)
N8	0.055 (2)	0.0314 (17)	0.0344 (19)	0.0004 (15)	0.0110 (17)	−0.0014 (14)
C1	0.068 (3)	0.062 (3)	0.038 (2)	0.013 (2)	0.002 (2)	−0.009 (2)
C2	0.059 (3)	0.056 (3)	0.052 (3)	0.020 (2)	0.012 (2)	−0.004 (2)
C3	0.052 (3)	0.057 (3)	0.059 (3)	0.015 (2)	0.007 (2)	0.003 (2)
C4	0.052 (3)	0.061 (3)	0.037 (2)	0.004 (2)	0.005 (2)	0.000 (2)
C5	0.042 (3)	0.034 (2)	0.039 (2)	0.0020 (18)	0.004 (2)	−0.0001 (18)
C6	0.044 (3)	0.033 (2)	0.033 (2)	−0.0031 (18)	0.003 (2)	−0.0015 (18)
C7	0.042 (3)	0.041 (2)	0.035 (2)	−0.0011 (19)	0.003 (2)	0.0021 (18)
C8	0.052 (3)	0.074 (3)	0.038 (2)	0.012 (2)	0.004 (2)	−0.014 (2)
C9	0.096 (4)	0.141 (5)	0.044 (3)	0.022 (3)	0.022 (3)	0.018 (3)
C10	0.043 (2)	0.044 (2)	0.031 (2)	0.0070 (19)	0.0064 (19)	0.0028 (19)
C11	0.068 (3)	0.041 (3)	0.050 (3)	0.002 (2)	0.002 (2)	0.002 (2)
C12	0.083 (4)	0.049 (3)	0.068 (3)	0.018 (3)	0.012 (3)	0.017 (2)
C13	0.066 (3)	0.093 (4)	0.040 (3)	0.021 (3)	−0.004 (2)	0.015 (3)
C14	0.055 (3)	0.079 (3)	0.042 (3)	−0.002 (2)	−0.001 (2)	−0.007 (2)
C15	0.054 (3)	0.048 (2)	0.038 (2)	0.001 (2)	0.006 (2)	0.003 (2)
C16	0.062 (3)	0.064 (3)	0.041 (3)	−0.010 (2)	0.006 (2)	−0.009 (2)
C17	0.059 (3)	0.069 (3)	0.056 (3)	−0.014 (2)	−0.003 (2)	−0.005 (2)
C18	0.052 (3)	0.072 (3)	0.066 (3)	−0.014 (2)	0.012 (3)	0.001 (3)
C19	0.057 (3)	0.070 (3)	0.047 (3)	−0.006 (2)	0.009 (2)	−0.004 (2)
C20	0.048 (3)	0.037 (2)	0.043 (2)	0.0023 (19)	0.008 (2)	−0.0002 (18)
C21	0.049 (3)	0.032 (2)	0.034 (2)	0.0051 (18)	0.005 (2)	−0.0022 (17)
C22	0.053 (3)	0.031 (2)	0.039 (2)	0.0023 (18)	0.009 (2)	−0.0044 (18)
C23	0.062 (3)	0.059 (3)	0.041 (3)	−0.006 (2)	0.010 (2)	−0.012 (2)
C24	0.107 (4)	0.090 (4)	0.043 (3)	0.000 (3)	−0.008 (3)	0.015 (3)
C25	0.053 (3)	0.044 (2)	0.032 (2)	0.001 (2)	0.0100 (19)	0.0029 (18)
C26	0.067 (3)	0.041 (3)	0.059 (3)	0.000 (2)	0.012 (2)	0.006 (2)
C27	0.077 (4)	0.062 (3)	0.070 (3)	−0.006 (3)	0.007 (3)	0.024 (3)
C28	0.070 (4)	0.108 (4)	0.044 (3)	−0.005 (3)	0.013 (3)	0.018 (3)
C29	0.073 (3)	0.081 (4)	0.044 (3)	0.012 (3)	0.018 (2)	−0.002 (2)
C30	0.069 (3)	0.050 (3)	0.039 (2)	0.007 (2)	0.013 (2)	0.001 (2)

Geometric parameters (Å, º) top

Cu1—N3ⁱ	1.989 (3)	C9—H9A	0.9600
Cu1—N1	2.029 (3)	C9—H9B	0.9600
Cu1—N2	2.179 (3)	C9—H9C	0.9600
Cu1—Cl2	2.2657 (11)	C10—C15	1.372 (5)
Cu1—Cl1	2.2734 (10)	C10—C11	1.374 (4)
Cu2—N7ⁱⁱ	1.977 (3)	C11—C12	1.367 (5)
Cu2—N5	2.018 (3)	C11—H11	0.9300
Cu2—N6	2.181 (3)	C12—C13	1.366 (5)
Cu2—Cl4	2.2637 (12)	C12—H12	0.9300
Cu2—Cl3	2.2804 (11)	C13—C14	1.371 (5)
N1—C1	1.328 (4)	C13—H13	0.9300
N1—C5	1.340 (4)	C14—C15	1.373 (5)
N2—C6	1.302 (4)	C14—H14	0.9300
N2—N3	1.382 (3)	C15—H15	0.9300
N3—C7	1.311 (4)	C16—C17	1.382 (5)
N3—Cu1ⁱ	1.989 (3)	C16—H16	0.9300
N4—C6	1.362 (4)	C17—C18	1.352 (5)
N4—C7	1.365 (4)	C17—H17	0.9300
N4—C10	1.438 (4)	C18—C19	1.380 (5)
N5—C16	1.322 (4)	C18—H18	0.9300
N5—C20	1.342 (4)	C19—C20	1.371 (5)
N6—C21	1.309 (4)	C19—H19	0.9300
N6—N7	1.371 (3)	C20—C21	1.457 (5)
N7—C22	1.317 (4)	C22—C23	1.480 (5)
N7—Cu2ⁱⁱ	1.977 (3)	C23—C24	1.515 (5)
N8—C22	1.358 (4)	C23—H23A	0.9700
N8—C21	1.364 (4)	C23—H23B	0.9700
N8—C25	1.457 (4)	C24—H24A	0.9600
C1—C2	1.374 (5)	C24—H24B	0.9600
C1—H1	0.9300	C24—H24C	0.9600
C2—C3	1.366 (5)	C25—C26	1.367 (4)
C2—H2	0.9300	C25—C30	1.373 (4)
C3—C4	1.382 (4)	C26—C27	1.374 (5)
C3—H3	0.9300	C26—H26	0.9300
C4—C5	1.362 (5)	C27—C28	1.379 (5)
C4—H4	0.9300	C27—H27	0.9300
C5—C6	1.471 (4)	C28—C29	1.369 (5)
C7—C8	1.482 (4)	C28—H28	0.9300
C8—C9	1.522 (5)	C29—C30	1.375 (5)
C8—H8A	0.9700	C29—H29	0.9300
C8—H8B	0.9700	C30—H30	0.9300

N3ⁱ—Cu1—N1	172.45 (11)	H9A—C9—H9B	109.5
N3ⁱ—Cu1—N2	95.70 (10)	C8—C9—H9C	109.5
N1—Cu1—N2	77.15 (11)	H9A—C9—H9C	109.5
N3ⁱ—Cu1—Cl2	91.19 (9)	H9B—C9—H9C	109.5
N1—Cu1—Cl2	89.93 (9)	C15—C10—C11	121.0 (4)
N2—Cu1—Cl2	116.78 (8)	C15—C10—N4	119.9 (3)
N3ⁱ—Cu1—Cl1	92.67 (8)	C11—C10—N4	118.9 (3)
N1—Cu1—Cl1	92.30 (8)	C12—C11—C10	118.6 (4)
N2—Cu1—Cl1	112.17 (8)	C12—C11—H11	120.7
Cl2—Cu1—Cl1	130.20 (4)	C10—C11—H11	120.7
N7ⁱⁱ—Cu2—N5	173.36 (11)	C13—C12—C11	121.2 (4)
N7ⁱⁱ—Cu2—N6	96.47 (10)	C13—C12—H12	119.4
N5—Cu2—N6	77.15 (11)	C11—C12—H12	119.4
N7ⁱⁱ—Cu2—Cl4	90.06 (9)	C12—C13—C14	119.7 (4)
N5—Cu2—Cl4	90.60 (9)	C12—C13—H13	120.2
N6—Cu2—Cl4	111.51 (8)	C14—C13—H13	120.2
N7ⁱⁱ—Cu2—Cl3	91.26 (8)	C13—C14—C15	120.1 (4)
N5—Cu2—Cl3	92.95 (8)	C13—C14—H14	119.9
N6—Cu2—Cl3	113.03 (8)	C15—C14—H14	119.9
Cl4—Cu2—Cl3	134.97 (4)	C10—C15—C14	119.3 (4)
C1—N1—C5	117.9 (3)	C10—C15—H15	120.3
C1—N1—Cu1	122.4 (3)	C14—C15—H15	120.3
C5—N1—Cu1	119.3 (2)	N5—C16—C17	122.5 (4)
C6—N2—N3	106.7 (3)	N5—C16—H16	118.8
C6—N2—Cu1	111.1 (2)	C17—C16—H16	118.8
N3—N2—Cu1	141.9 (2)	C18—C17—C16	119.0 (4)
C7—N3—N2	108.3 (3)	C18—C17—H17	120.5
C7—N3—Cu1ⁱ	129.5 (2)	C16—C17—H17	120.5
N2—N3—Cu1ⁱ	122.2 (2)	C17—C18—C19	119.2 (4)
C6—N4—C7	105.2 (3)	C17—C18—H18	120.4
C6—N4—C10	130.0 (3)	C19—C18—H18	120.4
C7—N4—C10	124.5 (3)	C20—C19—C18	118.8 (4)
C16—N5—C20	118.4 (3)	C20—C19—H19	120.6
C16—N5—Cu2	122.0 (3)	C18—C19—H19	120.6
C20—N5—Cu2	119.4 (2)	N5—C20—C19	122.0 (3)
C21—N6—N7	107.3 (3)	N5—C20—C21	112.5 (3)
C21—N6—Cu2	111.1 (2)	C19—C20—C21	125.4 (3)
N7—N6—Cu2	141.4 (2)	N6—C21—N8	109.6 (3)
C22—N7—N6	108.4 (3)	N6—C21—C20	119.5 (3)
C22—N7—Cu2ⁱⁱ	129.7 (3)	N8—C21—C20	130.9 (3)
N6—N7—Cu2ⁱⁱ	122.0 (2)	N7—C22—N8	108.7 (3)
C22—N8—C21	106.1 (3)	N7—C22—C23	125.6 (3)
C22—N8—C25	124.3 (3)	N8—C22—C23	125.7 (3)
C21—N8—C25	129.6 (3)	C22—C23—C24	114.7 (3)
N1—C1—C2	123.0 (4)	C22—C23—H23A	108.6
N1—C1—H1	118.5	C24—C23—H23A	108.6
C2—C1—H1	118.5	C22—C23—H23B	108.6
C3—C2—C1	118.6 (4)	C24—C23—H23B	108.6
C3—C2—H2	120.7	H23A—C23—H23B	107.6
C1—C2—H2	120.7	C23—C24—H24A	109.5
C2—C3—C4	119.0 (4)	C23—C24—H24B	109.5
C2—C3—H3	120.5	H24A—C24—H24B	109.5
C4—C3—H3	120.5	C23—C24—H24C	109.5
C5—C4—C3	118.9 (4)	H24A—C24—H24C	109.5
C5—C4—H4	120.5	H24B—C24—H24C	109.5
C3—C4—H4	120.5	C26—C25—C30	122.4 (4)
N1—C5—C4	122.5 (3)	C26—C25—N8	119.8 (3)
N1—C5—C6	111.9 (3)	C30—C25—N8	117.8 (3)
C4—C5—C6	125.5 (3)	C25—C26—C27	118.3 (4)
N2—C6—N4	110.7 (3)	C25—C26—H26	120.9
N2—C6—C5	119.8 (3)	C27—C26—H26	120.9
N4—C6—C5	129.3 (4)	C26—C27—C28	120.2 (4)
N3—C7—N4	109.1 (3)	C26—C27—H27	119.9
N3—C7—C8	126.4 (4)	C28—C27—H27	119.9
N4—C7—C8	124.4 (3)	C29—C28—C27	120.6 (4)
C7—C8—C9	115.4 (3)	C29—C28—H28	119.7
C7—C8—H8A	108.4	C27—C28—H28	119.7
C9—C8—H8A	108.4	C28—C29—C30	119.8 (4)
C7—C8—H8B	108.4	C28—C29—H29	120.1
C9—C8—H8B	108.4	C30—C29—H29	120.1
H8A—C8—H8B	107.5	C25—C30—C29	118.8 (4)
C8—C9—H9A	109.5	C25—C30—H30	120.6
C8—C9—H9B	109.5	C29—C30—H30	120.6

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl2ⁱⁱⁱ	0.93	2.78	3.445 (4)	129
C15—H15···Cl3^iv	0.93	2.78	3.579 (4)	145
C16—H16···Cl1^v	0.93	2.76	3.518 (4)	139
C19—H19···Cl4^vi	0.93	2.69	3.365 (4)	130

Symmetry codes: (iii) −x+2, −y+2, −z; (iv) −x+1, −y+2, −z+1; (v) x, y, z+1; (vi) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂Cl₄(C₁₅H₁₄N₄)₂]
M_r	769.48
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	9.3395 (11), 12.8096 (14), 13.9234 (16)
α, β, γ (°)	92.533 (2), 94.596 (2), 90.452 (2)
V (Å³)	1658.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.64
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.62, 0.68
No. of measured, independent and observed [I > 2σ(I)] reflections	8289, 5716, 4065
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.069, 1.05
No. of reflections	5716
No. of parameters	399
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.40

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).