Dichlorido[1-(1,10-phenanthrolin-2-yl)-2-pyridone]copper(II)

Li, J.M.

doi:10.1107/S160053680801948X

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m982

doi:10.1107/S160053680801948X

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Dichlorido[1-(1,10-phenanthrolin-2-yl)-2-pyridone]copper(II)

Jin Min Li ^a ^*

^aChemistry and Chemical Engineering College, Shanxi Datong University, Datong 037008, People's Republic of China
^*Correspondence e-mail: jinminli1957@yahoo.com.cn

(Received 20 June 2008; accepted 26 June 2008; online 5 July 2008)

In the title mononuclear complex, [CuCl₂(C₁₇H₁₁N₃O)], the Cu^II ion is in a distorted square-pyramidal coordination environment. The crystal structure is stabilized by various π–π stacking interactions in which the benzene ring, a pyridine ring and the five-membered CuN₂C₂ ring are involved. The centroid–centroid distances range from 3.5631 (15) to 3.5666 (16) Å.

Related literature

For a related structure, see: Liu et al. (2008 ).

Experimental

Crystal data

[CuCl₂(C₁₇H₁₁N₃O)]
M_r = 407.73
Monoclinic, P 2₁ /c
a = 7.3653 (12) Å
b = 13.811 (2) Å
c = 14.994 (2) Å
β = 98.416 (2)°
V = 1508.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.81 mm⁻¹
T = 298 (2) K
0.38 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.546, T_max = 0.812
8630 measured reflections
3265 independent reflections
2706 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.102
S = 1.11
3265 reflections
217 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cl1—Cu1	2.2362 (8)
Cl2—Cu1	2.3740 (8)
Cu1—N2	2.0165 (19)
Cu1—N1	2.042 (2)
Cu1—O1	2.1337 (18)

N2—Cu1—N1	80.75 (8)
N2—Cu1—O1	80.70 (7)
N1—Cu1—O1	147.25 (8)
N2—Cu1—Cl1	158.03 (7)
N1—Cu1—Cl1	92.93 (6)
O1—Cu1—Cl1	94.29 (5)
N2—Cu1—Cl2	97.87 (6)
N1—Cu1—Cl2	115.81 (6)
O1—Cu1—Cl2	93.32 (6)
Cl1—Cu1—Cl2	103.79 (3)

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801948X/lh2647sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801948X/lh2647Isup2.hkl

checkCIF report

Comment top

Derivatives of 1,10-phenanthroline play an important role in modern coordination chemistry and the complex with 1-(1,10-phenanthrolin-2-yl)-2-pyridone as bridging ligand and termial ligand has already been reported (Liu et al., 2008). Herein the crystal structure of the title complex with 1-(1,10-phenanthrolin-2-yl)-2-pyridone as terminal ligand is reported.

Fig. 1 shows the moleculuar structure, revealing that the atom Cu^II ion is in a distorted square-pyramidal coordination environment, with atom Cl2 in the apical position. There are π–π stacking interactions involving symmetry-related complex molecules, the relevant distances being Cg1···Cg2ⁱ = 3.5631 (15) Å and Cg1···Cg2ⁱ_perp = 3.355 Å and α = 4.35°; Cg2···Cg3ⁱⁱ = 3.5568 (16) Å and Cg2···Cg3ⁱⁱ_perp = 3.450 Å and α = 1.81°; Cg2···Cg2ⁱ = 3.5666 (16) Å and Cg2···Cg2ⁱ_perp = 3.407 Å and α = 0.00° [symmetry codes: (i) 1-x, 2-x, 1-x; (ii) -x, 2-y, 1-x; Cg1, Cg2 and Cg3 are the centroids of the Cu1/N1/N2/C8/C14 ring, C8/C9/C11-C14 ring amd N1/C13-C17 ring, respectively; Cgi···Cgj_perp is the perpendicular distance from ring Cgi to ring Cgj; α is the dihedral angle between ring plane Cgi and ring plane Cgj]. These π–π stacking interactions help stabilize the crystal structure.

Related literature top

For a related structure, see: Liu et al. (2008).

Experimental top

A 10 ml methanol solution of 1-(1,10-phenanthrolin-2-yl)-2-pyridone (0.1648 g, 0.603 mmol) was added into a 10 ml methanol solution containing CuCl₂ (0.1025 g, 0.601 mmol) and the mixture was stirred for a few minutes. The green single crystals were obtained after the filtrate had been allowed to stand at room temperature for two weeks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. The molecular structure of the title complex with atom-numbering scheme. Displacement ellipsoids are shown at the 30% probability level

Dichlorido[1-(1,10-phenanthrolin-2-yl)-2-pyridone]copper(II) top

Crystal data top

[CuCl₂(C₁₇H₁₁N₃O)]	F(000) = 820
M_r = 407.73	D_x = 1.795 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3380 reflections
a = 7.3653 (12) Å	θ = 2.8–28.1°
b = 13.811 (2) Å	µ = 1.81 mm⁻¹
c = 14.994 (2) Å	T = 298 K
β = 98.416 (2)°	Block, green
V = 1508.8 (4) Å³	0.38 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3265 independent reflections
Radiation source: fine-focus sealed tube	2706 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.546, T_max = 0.812	k = −16→17
8630 measured reflections	l = −16→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0547P)² + 0.1919P] where P = (F_o² + 2F_c²)/3
3265 reflections	(Δ/σ)_max = 0.002
217 parameters	Δρ_max = 0.64 e Å⁻³
1 restraint	Δρ_min = −0.66 e Å⁻³

Crystal data top

[CuCl₂(C₁₇H₁₁N₃O)]	V = 1508.8 (4) Å³
M_r = 407.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3653 (12) Å	µ = 1.81 mm⁻¹
b = 13.811 (2) Å	T = 298 K
c = 14.994 (2) Å	0.38 × 0.16 × 0.12 mm
β = 98.416 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3265 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2706 reflections with I > 2σ(I)
T_min = 0.546, T_max = 0.812	R_int = 0.035
8630 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.102	H-atom parameters constrained
S = 1.11	Δρ_max = 0.64 e Å⁻³
3265 reflections	Δρ_min = −0.66 e Å⁻³
217 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 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
C1	0.3230 (4)	1.05721 (18)	0.15163 (16)	0.0310 (5)
C2	0.3160 (4)	1.0755 (2)	0.05804 (17)	0.0378 (6)
H2	0.3550	1.1354	0.0397	0.045*
C3	0.2546 (4)	1.0089 (2)	−0.00543 (17)	0.0397 (6)
H3	0.2518	1.0236	−0.0662	0.048*
C4	0.1951 (4)	0.9179 (2)	0.01991 (18)	0.0405 (6)
H4	0.1498	0.8725	−0.0236	0.049*
C5	0.2045 (4)	0.89731 (19)	0.10802 (18)	0.0371 (6)
H5	0.1638	0.8373	0.1252	0.045*
C6	0.2990 (3)	0.93054 (17)	0.26475 (16)	0.0291 (5)
C7	0.3620 (4)	0.83639 (18)	0.28418 (18)	0.0352 (6)
H7	0.3909	0.7963	0.2385	0.042*
C8	0.2832 (3)	0.95921 (16)	0.41397 (15)	0.0254 (5)
C9	0.3410 (3)	0.86537 (16)	0.43983 (17)	0.0289 (5)
C10	0.3804 (4)	0.80403 (18)	0.37072 (19)	0.0358 (6)
H10	0.4194	0.7409	0.3841	0.043*
C11	0.3575 (4)	0.83935 (19)	0.53288 (18)	0.0354 (6)
H11	0.4002	0.7780	0.5510	0.042*
C12	0.3121 (4)	0.9024 (2)	0.59522 (17)	0.0361 (6)
H12	0.3233	0.8835	0.6553	0.043*
C13	0.2472 (3)	0.99763 (18)	0.57023 (16)	0.0308 (5)
C14	0.2373 (3)	1.02632 (17)	0.47986 (15)	0.0258 (5)
C15	0.1357 (4)	1.17865 (19)	0.50840 (17)	0.0339 (6)
H15	0.0987	1.2402	0.4882	0.041*
C16	0.1378 (4)	1.1564 (2)	0.59914 (18)	0.0389 (6)
H16	0.1007	1.2022	0.6382	0.047*
C17	0.1950 (4)	1.06686 (19)	0.63025 (17)	0.0362 (6)
H17	0.1993	1.0518	0.6910	0.043*
Cl1	0.25172 (13)	1.29316 (5)	0.33181 (5)	0.0508 (2)
Cl2	−0.07342 (10)	1.12202 (5)	0.21487 (5)	0.04360 (19)
Cu1	0.20539 (5)	1.13365 (2)	0.316143 (19)	0.03221 (13)
N1	0.1845 (3)	1.11538 (14)	0.44938 (13)	0.0282 (4)
N2	0.2618 (3)	0.99094 (14)	0.32770 (12)	0.0262 (4)
N3	0.2737 (3)	0.96350 (15)	0.17385 (13)	0.0299 (5)
O1	0.3712 (3)	1.11913 (12)	0.21153 (13)	0.0375 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0304 (14)	0.0318 (13)	0.0311 (13)	0.0018 (10)	0.0054 (10)	−0.0030 (11)
C2	0.0418 (17)	0.0382 (15)	0.0345 (14)	−0.0002 (12)	0.0091 (12)	0.0034 (11)
C3	0.0423 (17)	0.0498 (16)	0.0270 (13)	0.0047 (13)	0.0049 (11)	−0.0005 (12)
C4	0.0477 (18)	0.0415 (15)	0.0310 (14)	−0.0004 (13)	0.0012 (12)	−0.0108 (11)
C5	0.0443 (17)	0.0306 (13)	0.0353 (14)	−0.0014 (12)	0.0018 (12)	−0.0057 (11)
C6	0.0308 (14)	0.0287 (12)	0.0279 (12)	−0.0011 (10)	0.0043 (10)	−0.0021 (10)
C7	0.0404 (16)	0.0271 (12)	0.0387 (14)	0.0034 (11)	0.0072 (12)	−0.0045 (11)
C8	0.0208 (13)	0.0263 (11)	0.0284 (12)	−0.0017 (9)	0.0009 (9)	0.0023 (9)
C9	0.0239 (14)	0.0275 (12)	0.0348 (13)	−0.0011 (9)	0.0025 (10)	0.0048 (9)
C10	0.0350 (16)	0.0263 (13)	0.0448 (15)	0.0032 (11)	0.0009 (11)	0.0033 (11)
C11	0.0306 (15)	0.0332 (13)	0.0409 (15)	−0.0015 (11)	0.0002 (11)	0.0134 (11)
C12	0.0358 (16)	0.0427 (14)	0.0287 (13)	−0.0075 (12)	0.0011 (11)	0.0111 (11)
C13	0.0242 (14)	0.0394 (13)	0.0287 (12)	−0.0097 (11)	0.0030 (10)	0.0034 (11)
C14	0.0199 (12)	0.0300 (12)	0.0266 (12)	−0.0030 (9)	0.0007 (9)	0.0013 (9)
C15	0.0366 (15)	0.0319 (13)	0.0330 (13)	0.0003 (11)	0.0041 (11)	−0.0058 (11)
C16	0.0396 (17)	0.0454 (15)	0.0328 (14)	−0.0039 (12)	0.0093 (12)	−0.0096 (12)
C17	0.0349 (16)	0.0472 (16)	0.0266 (13)	−0.0104 (12)	0.0050 (11)	−0.0015 (11)
Cl1	0.0949 (7)	0.0249 (3)	0.0346 (4)	0.0034 (3)	0.0158 (4)	0.0007 (3)
Cl2	0.0389 (4)	0.0562 (4)	0.0337 (4)	0.0037 (3)	−0.0013 (3)	0.0073 (3)
Cu1	0.0477 (3)	0.02408 (19)	0.02382 (19)	0.00415 (13)	0.00175 (14)	0.00028 (11)
N1	0.0279 (12)	0.0295 (10)	0.0264 (10)	−0.0004 (8)	0.0018 (8)	−0.0009 (8)
N2	0.0284 (11)	0.0228 (10)	0.0271 (10)	0.0009 (8)	0.0033 (8)	−0.0002 (8)
N3	0.0362 (13)	0.0280 (11)	0.0263 (10)	0.0009 (9)	0.0066 (9)	−0.0024 (8)
O1	0.0475 (12)	0.0328 (10)	0.0335 (10)	−0.0075 (8)	0.0104 (8)	−0.0047 (8)

Geometric parameters (Å, º) top

C1—O1	1.253 (3)	C9—C11	1.429 (4)
C1—N3	1.397 (3)	C10—H10	0.9300
C1—C2	1.419 (3)	C11—C12	1.355 (4)
C2—C3	1.353 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.430 (4)
C3—C4	1.402 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.403 (3)
C4—C5	1.343 (4)	C13—C17	1.405 (4)
C4—H4	0.9300	C14—N1	1.349 (3)
C5—N3	1.386 (3)	C15—N1	1.330 (3)
C5—H5	0.9300	C15—C16	1.393 (4)
C6—N2	1.318 (3)	C15—H15	0.9300
C6—C7	1.397 (3)	C16—C17	1.366 (4)
C6—N3	1.423 (3)	C16—H16	0.9300
C7—C10	1.360 (4)	C17—H17	0.9300
C7—H7	0.9300	Cl1—Cu1	2.2362 (8)
C8—N2	1.353 (3)	Cl2—Cu1	2.3740 (8)
C8—C9	1.401 (3)	Cu1—N2	2.0165 (19)
C8—C14	1.431 (3)	Cu1—N1	2.042 (2)
C9—C10	1.401 (4)	Cu1—O1	2.1337 (18)

O1—C1—N3	121.2 (2)	C14—C13—C17	116.5 (2)
O1—C1—C2	123.5 (2)	C14—C13—C12	118.7 (2)
N3—C1—C2	115.3 (2)	C17—C13—C12	124.8 (2)
C3—C2—C1	122.3 (3)	N1—C14—C13	123.8 (2)
C3—C2—H2	118.8	N1—C14—C8	116.2 (2)
C1—C2—H2	118.8	C13—C14—C8	120.0 (2)
C2—C3—C4	120.3 (2)	N1—C15—C16	122.7 (2)
C2—C3—H3	119.9	N1—C15—H15	118.7
C4—C3—H3	119.9	C16—C15—H15	118.7
C5—C4—C3	118.9 (3)	C17—C16—C15	119.5 (2)
C5—C4—H4	120.6	C17—C16—H16	120.3
C3—C4—H4	120.6	C15—C16—H16	120.3
C4—C5—N3	121.4 (3)	C16—C17—C13	119.8 (2)
C4—C5—H5	119.3	C16—C17—H17	120.1
N3—C5—H5	119.3	C13—C17—H17	120.1
N2—C6—C7	122.5 (2)	N2—Cu1—N1	80.75 (8)
N2—C6—N3	118.1 (2)	N2—Cu1—O1	80.70 (7)
C7—C6—N3	119.4 (2)	N1—Cu1—O1	147.25 (8)
C10—C7—C6	119.2 (2)	N2—Cu1—Cl1	158.03 (7)
C10—C7—H7	120.4	N1—Cu1—Cl1	92.93 (6)
C6—C7—H7	120.4	O1—Cu1—Cl1	94.29 (5)
N2—C8—C9	123.5 (2)	N2—Cu1—Cl2	97.87 (6)
N2—C8—C14	116.4 (2)	N1—Cu1—Cl2	115.81 (6)
C9—C8—C14	120.1 (2)	O1—Cu1—Cl2	93.32 (6)
C8—C9—C10	116.2 (2)	Cl1—Cu1—Cl2	103.79 (3)
C8—C9—C11	118.8 (2)	C15—N1—C14	117.8 (2)
C10—C9—C11	125.0 (2)	C15—N1—Cu1	129.52 (17)
C7—C10—C9	120.3 (2)	C14—N1—Cu1	112.63 (15)
C7—C10—H10	119.9	C6—N2—C8	118.2 (2)
C9—C10—H10	119.9	C6—N2—Cu1	128.23 (16)
C12—C11—C9	121.2 (2)	C8—N2—Cu1	113.10 (15)
C12—C11—H11	119.4	C5—N3—C1	121.5 (2)
C9—C11—H11	119.4	C5—N3—C6	117.0 (2)
C11—C12—C13	121.1 (2)	C1—N3—C6	121.5 (2)
C11—C12—H12	119.4	C1—O1—Cu1	117.28 (17)
C13—C12—H12	119.4

O1—C1—C2—C3	−176.6 (3)	Cl1—Cu1—N1—C15	25.1 (2)
N3—C1—C2—C3	4.1 (4)	Cl2—Cu1—N1—C15	−81.8 (2)
C1—C2—C3—C4	−0.1 (4)	N2—Cu1—N1—C14	7.26 (17)
C2—C3—C4—C5	−1.7 (4)	O1—Cu1—N1—C14	−49.0 (2)
C3—C4—C5—N3	−0.8 (4)	Cl1—Cu1—N1—C14	−151.57 (16)
N2—C6—C7—C10	2.2 (4)	Cl2—Cu1—N1—C14	101.59 (16)
N3—C6—C7—C10	−177.9 (2)	C7—C6—N2—C8	−1.1 (4)
N2—C8—C9—C10	1.1 (4)	N3—C6—N2—C8	179.0 (2)
C14—C8—C9—C10	179.1 (2)	C7—C6—N2—Cu1	170.42 (19)
N2—C8—C9—C11	−179.5 (2)	N3—C6—N2—Cu1	−9.5 (3)
C14—C8—C9—C11	−1.6 (3)	C9—C8—N2—C6	−0.6 (4)
C6—C7—C10—C9	−1.6 (4)	C14—C8—N2—C6	−178.6 (2)
C8—C9—C10—C7	0.0 (4)	C9—C8—N2—Cu1	−173.35 (19)
C11—C9—C10—C7	−179.3 (3)	C14—C8—N2—Cu1	8.6 (3)
C8—C9—C11—C12	2.4 (4)	N1—Cu1—N2—C6	179.5 (2)
C10—C9—C11—C12	−178.3 (3)	O1—Cu1—N2—C6	−27.6 (2)
C9—C11—C12—C13	−0.5 (4)	Cl1—Cu1—N2—C6	−105.8 (2)
C11—C12—C13—C14	−2.2 (4)	Cl2—Cu1—N2—C6	64.5 (2)
C11—C12—C13—C17	179.1 (3)	N1—Cu1—N2—C8	−8.60 (16)
C17—C13—C14—N1	1.2 (4)	O1—Cu1—N2—C8	144.29 (17)
C12—C13—C14—N1	−177.6 (2)	Cl1—Cu1—N2—C8	66.0 (2)
C17—C13—C14—C8	−178.3 (2)	Cl2—Cu1—N2—C8	−123.61 (16)
C12—C13—C14—C8	3.0 (3)	C4—C5—N3—C1	5.1 (4)
N2—C8—C14—N1	−2.5 (3)	C4—C5—N3—C6	−172.4 (3)
C9—C8—C14—N1	179.4 (2)	O1—C1—N3—C5	174.1 (2)
N2—C8—C14—C13	177.0 (2)	C2—C1—N3—C5	−6.5 (3)
C9—C8—C14—C13	−1.1 (3)	O1—C1—N3—C6	−8.4 (4)
N1—C15—C16—C17	1.2 (4)	C2—C1—N3—C6	170.9 (2)
C15—C16—C17—C13	−1.3 (4)	N2—C6—N3—C5	−142.1 (2)
C14—C13—C17—C16	0.2 (4)	C7—C6—N3—C5	38.0 (3)
C12—C13—C17—C16	178.9 (3)	N2—C6—N3—C1	40.3 (3)
C16—C15—N1—C14	0.2 (4)	C7—C6—N3—C1	−139.6 (3)
C16—C15—N1—Cu1	−176.3 (2)	N3—C1—O1—Cu1	−46.7 (3)
C13—C14—N1—C15	−1.4 (4)	C2—C1—O1—Cu1	134.1 (2)
C8—C14—N1—C15	178.1 (2)	N2—Cu1—O1—C1	55.40 (19)
C13—C14—N1—Cu1	175.69 (18)	N1—Cu1—O1—C1	111.6 (2)
C8—C14—N1—Cu1	−4.8 (3)	Cl1—Cu1—O1—C1	−146.15 (19)
N2—Cu1—N1—C15	−176.1 (2)	Cl2—Cu1—O1—C1	−42.04 (19)
O1—Cu1—N1—C15	127.7 (2)

Experimental details

Crystal data
Chemical formula	[CuCl₂(C₁₇H₁₁N₃O)]
M_r	407.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.3653 (12), 13.811 (2), 14.994 (2)
β (°)	98.416 (2)
V (Å³)	1508.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.81
Crystal size (mm)	0.38 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.546, 0.812
No. of measured, independent and observed [I > 2σ(I)] reflections	8630, 3265, 2706
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.102, 1.11
No. of reflections	3265
No. of parameters	217
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.66

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cl1—Cu1	2.2362 (8)	Cu1—N1	2.042 (2)
Cl2—Cu1	2.3740 (8)	Cu1—O1	2.1337 (18)
Cu1—N2	2.0165 (19)

N2—Cu1—N1	80.75 (8)	O1—Cu1—Cl1	94.29 (5)
N2—Cu1—O1	80.70 (7)	N2—Cu1—Cl2	97.87 (6)
N1—Cu1—O1	147.25 (8)	N1—Cu1—Cl2	115.81 (6)
N2—Cu1—Cl1	158.03 (7)	O1—Cu1—Cl2	93.32 (6)
N1—Cu1—Cl1	92.93 (6)	Cl1—Cu1—Cl2	103.79 (3)

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, Q. S., Liu, L. D. & Shi, J. M. (2008). Acta Cryst. C64, m58–m60. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Gemany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar