Di-μ-chlorido-bis­[(1,10-phenanthroline-κ2N,N′)(trichloro­acetato-κO)copper(II)]

Shahverdizadeh, G.H.; Ng, S.W.; Tiekink, E.R.T.; Mirtamizdoust, B.

doi:10.1107/S1600536812003947

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m242-m243

doi:10.1107/S1600536812003947

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Di-μ-chlorido-bis[(1,10-phenanthroline-κ²N,N′)(trichloroacetato-κO)copper(II)]

Gholam Hossein Shahverdizadeh,^a ‡ Seik Weng Ng,^b,^c Edward R. T. Tiekink ^b ^* and Babak Mirtamizdoust ^d

^aDepartment of Chemistry, Faculty of Science, Tabriz Branch, Islamic Azad University, PO Box 1655, Tabriz, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, and ^dDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Tabriz, PO Box 5166616471, Tabriz, Iran
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 27 January 2012; accepted 30 January 2012; online 4 February 2012)

The title compound, [Cu₂(C₂Cl₃O₂)₂Cl₂(C₁₂H₈N₂)₂], features a centrosymmetric binuclear complex. The coordination geometry around the Cu^II atom is square-pyramidal, comprising two N atoms from a symmetrically chelating 1,10-phenanthroline ligand, one O atom from a trichloroacetate ligand and two Cl⁻ anions. In addition, there is a weak intramolecular Cu⋯O interaction of 2.9403 (14) Å involving the carbonyl O atom of the trichloroacetate ligand. The central Cu₂Cl₂ core takes the form of a rhombus, owing to the disparate Cu—Cl bond lengths. Molecules are connected in the crystal structure by C—H⋯Cl and C—H⋯O interactions.

Related literature

For background to crystal engineering studies of Cu^II 1,10-phenanthroline complexes, see: De Burgomaster et al. (2010 ). For specialized crystallization techniques, see: Harrowfield et al. (1996 ). For closely related binuclear Cu^II molecules with chloride, carboxylate and bipyridine ligands, see: Jiang et al. (2007 ); Zheng et al. (2008 ). For descriptive parameters of pyramidal and trigonal–bipyramidal geometries, see: Addison et al. (1984 ); Spek (2009 ).

Experimental

Crystal data

[Cu₂(C₂Cl₃O₂)₂Cl₂(C₁₂H₈N₂)₂]
M_r = 883.15
Monoclinic, P 2₁ /n
a = 9.2961 (2) Å
b = 17.3529 (2) Å
c = 10.6201 (2) Å
β = 115.269 (3)°
V = 1549.25 (5) Å³
Z = 2
Cu Kα radiation
μ = 8.43 mm⁻¹
T = 100 K
0.15 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.365, T_max = 0.678
11808 measured reflections
3233 independent reflections
3049 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.070
S = 1.05
3233 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu—O1	1.9491 (13)
Cu—N1	2.0163 (16)
Cu—N2	2.0214 (16)
Cu—Cl1	2.2811 (5)
Cu—Cl1ⁱ	2.6666 (5)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl3ⁱⁱ	0.95	2.80	3.679 (2)	154
C4—H4⋯O2ⁱⁱⁱ	0.95	2.49	3.302 (3)	144
C7—H7⋯Cl1^iv	0.95	2.73	3.638 (2)	159
Symmetry codes: (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+1; (iv) x, y, z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812003947/bt5807sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003947/bt5807Isup2.hkl

checkCIF report

Comment top

Research on copper^II phenanthroline derivatives continues to attract interest in the context of crystal engineering of copper coordination polymers (De Burgomaster et al., 2010). Herein, we report the title Cu^II complex, (I).

The Cu^II atom in binuclear (I), Fig. 1, is coordinated by two Cl atoms, which form dissimilar Cu—Cl bond lengths, two N atoms from a symmetrically chelating 1,10-phenanthroline ligand, and one O atom from a trichloroacetate ligand, Table 1. The structure of (I) is centrosymmetric and the central Cu₂O₂ has the form of a rhombus. The carbonyl-O2 atom forms a weak intramolecular Cu···O contact of 2.9403 (14) Å. The asymmetric mode of coordination of the carboxylate is reflected in the disparate C—O bond distances with the longer C13—O1 distance [1.270 (2) Å] being associated with the shorter Cu—O1 interaction, and the short C13—O2 distance [1.220 (2) Å] associated with the weaker Cu—O2 contact.

The resultant Cl₂N₂O donor set defines a square pyramid. This assignment is based on the value calculated for τ of 0.07 for the Cu atom, which compares to the τ values of 0.0 and 1.0 for ideal square pyramidal and trigonal bipyramidal geometries, respectively (Spek, 2009; Addison et al., 1984). In this description, the less tightly bound Clⁱ atom defines the axial site (i: 1 - x, 1 - y, 1 - z).

The observed coordination geometry in (I) resembles closely those found in the analogous structures with the carboxylate ligands being 2-anilinobenzoate (Jiang et al., 2007) and p-tolylthioacetate (Zheng et al., 2008).

In the crystal packing, molecules assembles into layers in the ac plane and are connected into the three dimensional architecture by C—H···Cl and C—H···O interactions, Fig. 2 and Table 2.

Related literature top

For background to crystal engineering studies of Cu^II 1,10-phenanthroline complexes, see: De Burgomaster et al. (2010). For specialized crystallization techniques, see: Harrowfield et al. (1996). For closely related binuclear Cu^II molecules with chloride, carboxylate and bipyridine ligands, see: Jiang et al. (2007); Zheng et al. (2008). For descriptive parameters of pyramidal and trigonal–bipyramidal geometries, see: Addison et al. (1984); Spek (2009).

Experimental top

1,10-Phenanthroline (1 mmol) was placed in one arm of a branched tube (Harrowfield et al., 1996) and a mixture of copper(II) chloride dihydrate (1 mmol) and trichloroacetic acid (1 mmol) in the other. Ethanol was then added to fill both arms, the tube was sealed and the ligand-containing arm immersed in a bath at 333 K, while the other was left at ambient temperature. After 3 d, crystals had deposited in the arm held at ambient temperature. They were filtered off, washed with acetone and ether, and air dried. Yield: 85%. M.p. = 530 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Unlabelled atoms are related by the symmetry operation 1 - x, 1 - y, 1 - z.
	Fig. 2. A view in projection down the a axis of the unit-cell contents for (I). The C—H···Cl and C—H···O interactions are shown as orange and blue dashed lines, respectively.

Di-µ-chlorido-bis[(1,10-phenanthroline- κ²N,N')(trichloroacetato-κO)copper(II)] top

Crystal data top

[Cu₂(C₂Cl₃O₂)₂Cl₂(C₁₂H₈N₂)₂]	F(000) = 876
M_r = 883.15	D_x = 1.893 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 7160 reflections
a = 9.2961 (2) Å	θ = 4.6–76.4°
b = 17.3529 (2) Å	µ = 8.43 mm⁻¹
c = 10.6201 (2) Å	T = 100 K
β = 115.269 (3)°	Chip, blue
V = 1549.25 (5) Å³	0.15 × 0.10 × 0.05 mm
Z = 2

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3233 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3049 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.019
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.6°, θ_min = 5.1°
ω scans	h = −6→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −21→21
T_min = 0.365, T_max = 0.678	l = −13→11
11808 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0394P)² + 1.203P] where P = (F_o² + 2F_c²)/3
3233 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Cu₂(C₂Cl₃O₂)₂Cl₂(C₁₂H₈N₂)₂]	V = 1549.25 (5) Å³
M_r = 883.15	Z = 2
Monoclinic, P2₁/n	Cu Kα radiation
a = 9.2961 (2) Å	µ = 8.43 mm⁻¹
b = 17.3529 (2) Å	T = 100 K
c = 10.6201 (2) Å	0.15 × 0.10 × 0.05 mm
β = 115.269 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3233 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3049 reflections with I > 2σ(I)
T_min = 0.365, T_max = 0.678	R_int = 0.019
11808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.05	Δρ_max = 0.52 e Å⁻³
3233 reflections	Δρ_min = −0.46 e Å⁻³
208 parameters

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

	x	y	z	U_iso*/U_eq
Cu	0.39736 (3)	0.560830 (15)	0.55506 (3)	0.01748 (9)
Cl1	0.34122 (6)	0.52569 (3)	0.33194 (5)	0.02267 (11)
Cl2	0.62010 (6)	0.73740 (3)	0.34999 (5)	0.02598 (11)
Cl3	0.39347 (5)	0.84979 (2)	0.34988 (5)	0.02186 (11)
Cl4	0.65647 (5)	0.80961 (3)	0.60933 (5)	0.02227 (11)
O1	0.51331 (16)	0.65057 (7)	0.53709 (14)	0.0210 (3)
O2	0.28218 (16)	0.71570 (8)	0.44642 (15)	0.0239 (3)
N1	0.24794 (19)	0.48328 (9)	0.57670 (16)	0.0185 (3)
N2	0.41913 (18)	0.59423 (9)	0.74473 (16)	0.0178 (3)
C1	0.2369 (2)	0.49090 (10)	0.70005 (19)	0.0169 (3)
C2	0.1599 (2)	0.42989 (11)	0.4880 (2)	0.0221 (4)
H2	0.1681	0.4236	0.4025	0.027*
C3	0.0548 (2)	0.38227 (11)	0.5162 (2)	0.0248 (4)
H3	−0.0075	0.3450	0.4496	0.030*
C4	0.0421 (2)	0.38958 (11)	0.6400 (2)	0.0237 (4)
H4	−0.0289	0.3578	0.6598	0.028*
C5	0.1367 (2)	0.44524 (11)	0.7372 (2)	0.0202 (4)
C6	0.1352 (2)	0.45803 (12)	0.8702 (2)	0.0241 (4)
H6	0.0657	0.4284	0.8956	0.029*
C7	0.2308 (2)	0.51143 (12)	0.9603 (2)	0.0242 (4)
H7	0.2299	0.5173	1.0489	0.029*
C8	0.3335 (2)	0.55923 (11)	0.9239 (2)	0.0198 (4)
C9	0.4369 (2)	0.61606 (12)	1.0113 (2)	0.0232 (4)
H9	0.4454	0.6235	1.1028	0.028*
C10	0.5252 (2)	0.66045 (11)	0.9628 (2)	0.0241 (4)
H10	0.5952	0.6987	1.0209	0.029*
C11	0.5113 (2)	0.64899 (11)	0.8271 (2)	0.0214 (4)
H11	0.5696	0.6813	0.7934	0.026*
C12	0.3321 (2)	0.54982 (10)	0.79196 (19)	0.0172 (3)
C13	0.4236 (2)	0.70725 (10)	0.47750 (19)	0.0182 (4)
C14	0.5177 (2)	0.77358 (11)	0.44580 (19)	0.0184 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.02157 (16)	0.01456 (15)	0.01898 (15)	−0.00160 (10)	0.01120 (12)	−0.00039 (9)
Cl1	0.0286 (2)	0.0222 (2)	0.0181 (2)	0.00446 (17)	0.01078 (18)	0.00221 (16)
Cl2	0.0307 (2)	0.0248 (2)	0.0302 (2)	−0.00004 (18)	0.0204 (2)	−0.00146 (18)
Cl3	0.0233 (2)	0.0184 (2)	0.0213 (2)	0.00170 (16)	0.00706 (18)	0.00467 (16)
Cl4	0.0216 (2)	0.0225 (2)	0.0189 (2)	−0.00312 (16)	0.00503 (17)	0.00003 (16)
O1	0.0221 (7)	0.0157 (6)	0.0266 (7)	0.0007 (5)	0.0118 (6)	0.0035 (5)
O2	0.0188 (7)	0.0208 (7)	0.0320 (7)	−0.0012 (5)	0.0108 (6)	0.0019 (6)
N1	0.0209 (7)	0.0157 (7)	0.0190 (7)	−0.0006 (6)	0.0086 (6)	0.0005 (6)
N2	0.0171 (7)	0.0166 (7)	0.0209 (7)	−0.0009 (6)	0.0091 (6)	−0.0021 (6)
C1	0.0169 (8)	0.0159 (8)	0.0177 (8)	0.0014 (7)	0.0072 (7)	0.0012 (7)
C2	0.0250 (10)	0.0192 (9)	0.0196 (9)	−0.0025 (7)	0.0072 (8)	−0.0030 (7)
C3	0.0226 (9)	0.0186 (9)	0.0276 (10)	−0.0034 (7)	0.0054 (8)	−0.0027 (7)
C4	0.0203 (9)	0.0185 (9)	0.0313 (10)	−0.0018 (7)	0.0100 (8)	0.0025 (8)
C5	0.0187 (9)	0.0175 (9)	0.0236 (9)	0.0008 (7)	0.0082 (8)	0.0040 (7)
C6	0.0254 (10)	0.0244 (9)	0.0273 (10)	0.0016 (8)	0.0157 (9)	0.0063 (8)
C7	0.0280 (10)	0.0263 (10)	0.0226 (9)	0.0039 (8)	0.0149 (8)	0.0032 (8)
C8	0.0192 (9)	0.0203 (9)	0.0190 (9)	0.0046 (7)	0.0074 (7)	0.0001 (7)
C9	0.0210 (9)	0.0254 (10)	0.0212 (9)	0.0051 (7)	0.0072 (8)	−0.0047 (7)
C10	0.0183 (9)	0.0230 (9)	0.0276 (10)	0.0010 (7)	0.0064 (8)	−0.0087 (8)
C11	0.0182 (9)	0.0180 (9)	0.0284 (10)	−0.0005 (7)	0.0103 (8)	−0.0046 (7)
C12	0.0162 (8)	0.0164 (8)	0.0195 (8)	0.0016 (7)	0.0080 (7)	0.0003 (7)
C13	0.0219 (9)	0.0163 (8)	0.0175 (8)	−0.0015 (7)	0.0094 (7)	−0.0017 (7)
C14	0.0185 (8)	0.0180 (8)	0.0191 (8)	0.0007 (7)	0.0083 (7)	0.0007 (7)

Geometric parameters (Å, º) top

Cu—O1	1.9491 (13)	C2—H2	0.9500
Cu—N1	2.0163 (16)	C3—C4	1.375 (3)
Cu—N2	2.0214 (16)	C3—H3	0.9500
Cu—Cl1	2.2811 (5)	C4—C5	1.413 (3)
Cu—Cl1ⁱ	2.6666 (5)	C4—H4	0.9500
Cl1—Cuⁱ	2.6666 (5)	C5—C6	1.436 (3)
Cl2—C14	1.7785 (19)	C6—C7	1.356 (3)
Cl3—C14	1.7652 (19)	C6—H6	0.9500
Cl4—C14	1.7772 (19)	C7—C8	1.437 (3)
O1—C13	1.270 (2)	C7—H7	0.9500
O2—C13	1.220 (2)	C8—C12	1.405 (3)
N1—C2	1.326 (2)	C8—C9	1.413 (3)
N1—C1	1.363 (2)	C9—C10	1.375 (3)
N2—C11	1.328 (2)	C9—H9	0.9500
N2—C12	1.359 (2)	C10—C11	1.405 (3)
C1—C5	1.402 (3)	C10—H10	0.9500
C1—C12	1.430 (2)	C11—H11	0.9500
C2—C3	1.406 (3)	C13—C14	1.567 (3)

O1—Cu—N1	168.83 (6)	C4—C5—C6	124.07 (18)
O1—Cu—N2	92.53 (6)	C7—C6—C5	121.42 (18)
N1—Cu—N2	81.87 (6)	C7—C6—H6	119.3
O1—Cu—Cl1	90.15 (4)	C5—C6—H6	119.3
N1—Cu—Cl1	94.40 (5)	C6—C7—C8	120.98 (18)
N2—Cu—Cl1	173.20 (5)	C6—C7—H7	119.5
O1—Cu—Cl1ⁱ	93.33 (4)	C8—C7—H7	119.5
N1—Cu—Cl1ⁱ	96.47 (5)	C12—C8—C9	116.77 (18)
N2—Cu—Cl1ⁱ	91.64 (5)	C12—C8—C7	118.51 (18)
Cl1—Cu—Cl1ⁱ	94.440 (17)	C9—C8—C7	124.72 (18)
Cu—Cl1—Cuⁱ	85.560 (17)	C10—C9—C8	119.49 (18)
C13—O1—Cu	113.24 (12)	C10—C9—H9	120.3
C2—N1—C1	118.26 (16)	C8—C9—H9	120.3
C2—N1—Cu	129.20 (13)	C9—C10—C11	119.75 (18)
C1—N1—Cu	112.51 (12)	C9—C10—H10	120.1
C11—N2—C12	118.75 (16)	C11—C10—H10	120.1
C11—N2—Cu	128.60 (13)	N2—C11—C10	121.87 (18)
C12—N2—Cu	112.52 (12)	N2—C11—H11	119.1
N1—C1—C5	123.17 (17)	C10—C11—H11	119.1
N1—C1—C12	116.54 (16)	N2—C12—C8	123.27 (17)
C5—C1—C12	120.28 (17)	N2—C12—C1	116.50 (16)
N1—C2—C3	122.30 (18)	C8—C12—C1	120.23 (17)
N1—C2—H2	118.9	O2—C13—O1	129.09 (18)
C3—C2—H2	118.9	O2—C13—C14	119.30 (16)
C4—C3—C2	120.00 (18)	O1—C13—C14	111.59 (16)
C4—C3—H3	120.0	C13—C14—Cl3	112.75 (13)
C2—C3—H3	120.0	C13—C14—Cl2	110.35 (12)
C3—C4—C5	118.77 (18)	Cl3—C14—Cl2	108.20 (10)
C3—C4—H4	120.6	C13—C14—Cl4	106.71 (12)
C5—C4—H4	120.6	Cl3—C14—Cl4	108.88 (10)
C1—C5—C4	117.49 (18)	Cl2—C14—Cl4	109.93 (10)
C1—C5—C6	118.44 (18)

O1—Cu—Cl1—Cuⁱ	93.35 (4)	C3—C4—C5—C1	1.0 (3)
N1—Cu—Cl1—Cuⁱ	−96.86 (5)	C3—C4—C5—C6	−179.53 (19)
Cl1ⁱ—Cu—Cl1—Cuⁱ	0.0	C1—C5—C6—C7	−1.7 (3)
N1—Cu—O1—C13	−31.8 (4)	C4—C5—C6—C7	178.81 (19)
N2—Cu—O1—C13	−91.39 (13)	C5—C6—C7—C8	2.2 (3)
Cl1—Cu—O1—C13	82.36 (12)	C6—C7—C8—C12	0.4 (3)
Cl1ⁱ—Cu—O1—C13	176.82 (12)	C6—C7—C8—C9	−179.89 (19)
O1—Cu—N1—C2	117.1 (3)	C12—C8—C9—C10	2.3 (3)
N2—Cu—N1—C2	177.57 (18)	C7—C8—C9—C10	−177.43 (19)
Cl1—Cu—N1—C2	3.29 (17)	C8—C9—C10—C11	0.2 (3)
Cl1ⁱ—Cu—N1—C2	−91.69 (17)	C12—N2—C11—C10	2.1 (3)
O1—Cu—N1—C1	−60.8 (4)	Cu—N2—C11—C10	−173.53 (14)
N2—Cu—N1—C1	−0.31 (13)	C9—C10—C11—N2	−2.5 (3)
Cl1—Cu—N1—C1	−174.59 (12)	C11—N2—C12—C8	0.5 (3)
Cl1ⁱ—Cu—N1—C1	90.43 (12)	Cu—N2—C12—C8	176.88 (14)
O1—Cu—N2—C11	−12.19 (17)	C11—N2—C12—C1	−179.01 (16)
N1—Cu—N2—C11	177.52 (17)	Cu—N2—C12—C1	−2.7 (2)
Cl1ⁱ—Cu—N2—C11	81.21 (16)	C9—C8—C12—N2	−2.7 (3)
O1—Cu—N2—C12	171.92 (13)	C7—C8—C12—N2	177.00 (17)
N1—Cu—N2—C12	1.63 (12)	C9—C8—C12—C1	176.80 (17)
Cl1ⁱ—Cu—N2—C12	−94.68 (12)	C7—C8—C12—C1	−3.5 (3)
C2—N1—C1—C5	−0.2 (3)	N1—C1—C12—N2	2.5 (2)
Cu—N1—C1—C5	177.90 (14)	C5—C1—C12—N2	−176.45 (16)
C2—N1—C1—C12	−179.17 (17)	N1—C1—C12—C8	−177.04 (16)
Cu—N1—C1—C12	−1.0 (2)	C5—C1—C12—C8	4.0 (3)
C1—N1—C2—C3	1.0 (3)	Cu—O1—C13—O2	9.5 (3)
Cu—N1—C2—C3	−176.75 (14)	Cu—O1—C13—C14	−171.79 (11)
N1—C2—C3—C4	−0.8 (3)	O2—C13—C14—Cl3	−6.2 (2)
C2—C3—C4—C5	−0.3 (3)	O1—C13—C14—Cl3	174.97 (13)
N1—C1—C5—C4	−0.8 (3)	O2—C13—C14—Cl2	−127.31 (16)
C12—C1—C5—C4	178.13 (17)	O1—C13—C14—Cl2	53.85 (18)
N1—C1—C5—C6	179.71 (17)	O2—C13—C14—Cl4	113.29 (17)
C12—C1—C5—C6	−1.4 (3)	O1—C13—C14—Cl4	−65.55 (17)

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
C2—H2···Cl3ⁱⁱ	0.95	2.80	3.679 (2)	154
C4—H4···O2ⁱⁱⁱ	0.95	2.49	3.302 (3)	144
C7—H7···Cl1^iv	0.95	2.73	3.638 (2)	159

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂Cl₃O₂)₂Cl₂(C₁₂H₈N₂)₂]
M_r	883.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.2961 (2), 17.3529 (2), 10.6201 (2)
β (°)	115.269 (3)
V (Å³)	1549.25 (5)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	8.43
Crystal size (mm)	0.15 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.365, 0.678
No. of measured, independent and observed [I > 2σ(I)] reflections	11808, 3233, 3049
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.070, 1.05
No. of reflections	3233
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.46

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu—O1	1.9491 (13)	Cu—Cl1	2.2811 (5)
Cu—N1	2.0163 (16)	Cu—Cl1ⁱ	2.6666 (5)
Cu—N2	2.0214 (16)

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
C2—H2···Cl3ⁱⁱ	0.95	2.80	3.679 (2)	154
C4—H4···O2ⁱⁱⁱ	0.95	2.49	3.302 (3)	144
C7—H7···Cl1^iv	0.95	2.73	3.638 (2)	159

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

Footnotes

‡Additional correspondence author, e-mail: shahverdizadeh@iaut.ac.ir.

Acknowledgements

The authors gratefully acknowledge support of this study by Tabriz Azad University, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM.C/HIR/MOHE/SC/12).

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