Di-μ-chlorido-bis­[chlorido(N,N′-dibenzyl­propane-1,2-diamine-κ2N,N′)copper(II)]

Liu, Y.-F.; Rong, D.-F.; Xia, H.-T.; Wang, D.-Q.

doi:10.1107/S1600536809044997

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1492

https://doi.org/10.1107/S1600536809044997

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Di-μ-chlorido-bis[chlorido(N,N′-dibenzylpropane-1,2-diamine-κ²N,N′)copper(II)]

Yu-Fen Liu,^a ^* Da-Fu Rong,^b Hai-Tao Xia ^a and Da-Qi Wang ^c

^aDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^bBeilun Entry–Exit Inspection and Quarantine Bureau of China, Zhejiang 315800, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China.
^*Correspondence e-mail: liu222005@hhit.edu.cn

(Received 16 October 2009; accepted 28 October 2009; online 31 October 2009)

In the title complex, [Cu₂Cl₄(C₁₇H₂₂N₂)₂], the Cu^II cation is coordinated by a N,N′-dibenzylpropane-1,2-diamine ligand and two Cl⁻ anions, and a Cl⁻ anion from an adjacent molecule further bridges to the Cu^II cation in the apical position, with a longer Cu—Cl distance of 2.9858 (18) Å, forming a centrosymmetric dimeric complex in which each Cu^II cation is in a distorted square-pyramidal geometry. Intramolecular N—H⋯Cl hydrogen bonding is observed in the dimeric complex.

Related literature

For Cu—Cl bond distances, see: Alves et al. (2004 ); Yang et al. (2007 ).

Experimental

Crystal data

[Cu₂Cl₄(C₁₇H₂₂N₂)₂]
M_r = 777.61
Monoclinic, C 2/c
a = 21.070 (2) Å
b = 13.7377 (17) Å
c = 13.2449 (16) Å
β = 114.317 (2)°
V = 3493.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.55 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.10 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.746, T_max = 0.860
8528 measured reflections
3077 independent reflections
1858 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.104
S = 1.06
3077 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N1	2.034 (4)
Cu1—N2	2.010 (4)
Cu1—Cl1	2.2598 (15)
Cu1—Cl2	2.2663 (17)
Cu1—Cl2ⁱ	2.9858 (18)
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl1ⁱ	0.91	2.51	3.386 (5)	161
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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: https://doi.org/10.1107/S1600536809044997/xu2644sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044997/xu2644Isup2.hkl

checkCIF report

Comment top

Copper(II) complexes bridged by a pair of Cl atoms have been widely investigated in both bioinorganic chemistry and coordination chemistry (Yang et al., 2007; Alves et al., 2004). As a further study of the structures of such complexes, the crystal structure of the title complex is reported here.

The molecular structure of the title complex is illustrated in Fig. 1. The Cu^II atom are in a distorted square-pyramidal coordination environment (Table 1). The two copper atoms are bridged by a pair of Cl atoms, resulting in complex with centro-symmetric structures. The apical Cu—Cl bond length is 2.9858 (18) Å, whic is longer than 2.737 Å reported by Alves et al. (2004), and 2.852 (1) and 2.971 (2) Å reported by Yang et al. (2007). The N—H···Cl hydrogen boding is present in the crystal structure (Table 2).

Related literature top

For Cu—Cl bond distances, see: Alves et al. (2004); Yang et al. (2007).

Experimental top

A solution of N,N'-dibenzylpropane-1,2-diamine (1 mmol) in ethanol (20 ml) and a solution of cupric chloride (1 mmol) in ethanol (10 ml) was mixed, the reaction mixture was stirred for 3 h at 323 K. The solution was then cooled slowly to room temperature and filtered. Blue crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution.

Structure description top

For Cu—Cl bond distances, see: Alves et al. (2004); Yang et al. (2007).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 dimeric complex structure showing the atom-labeling scheme. Displacement ellipsoids are at the 30% probability level. For clarity, H atomes have been omitted [symmetry code: (A) 1/2 - x, 1/2 - y, 1 - z].

Di-µ-chlorido-bis[chlorido(N,N'-dibenzylpropane-1,2- diamine-κ²N,N')copper(II)] top

Crystal data top

[Cu₂Cl₄(C₁₇H₂₂N₂)₂]	F(000) = 1608
M_r = 777.61	D_x = 1.478 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1854 reflections
a = 21.070 (2) Å	θ = 2.8–25.3°
b = 13.7377 (17) Å	µ = 1.55 mm⁻¹
c = 13.2449 (16) Å	T = 298 K
β = 114.317 (2)°	Block, blue
V = 3493.6 (7) Å³	0.20 × 0.18 × 0.10 mm
Z = 4

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3077 independent reflections
Radiation source: fine-focus sealed tube	1858 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→21
T_min = 0.746, T_max = 0.860	k = −16→16
8528 measured reflections	l = −10→15

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0084P)² + 19.8791P] where P = (F_o² + 2F_c²)/3
3077 reflections	(Δ/σ)_max = 0.011
199 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Cu₂Cl₄(C₁₇H₂₂N₂)₂]	V = 3493.6 (7) Å³
M_r = 777.61	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 21.070 (2) Å	µ = 1.55 mm⁻¹
b = 13.7377 (17) Å	T = 298 K
c = 13.2449 (16) Å	0.20 × 0.18 × 0.10 mm
β = 114.317 (2)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3077 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1858 reflections with I > 2σ(I)
T_min = 0.746, T_max = 0.860	R_int = 0.052
8528 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0084P)² + 19.8791P] where P = (F_o² + 2F_c²)/3
3077 reflections	Δρ_max = 0.59 e Å⁻³
199 parameters	Δρ_min = −0.67 e Å⁻³

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
Cu1	0.19407 (3)	0.17462 (5)	0.40049 (6)	0.0413 (2)
Cl1	0.10161 (7)	0.26002 (11)	0.39737 (13)	0.0528 (4)
Cl2	0.23408 (8)	0.13479 (12)	0.58229 (13)	0.0534 (4)
N1	0.1603 (2)	0.1813 (3)	0.2330 (4)	0.0419 (11)
H1	0.1558	0.2458	0.2160	0.050*
N2	0.2780 (2)	0.1094 (3)	0.3951 (4)	0.0414 (12)
H2	0.3158	0.1307	0.4549	0.050*
C1	0.2153 (3)	0.1442 (4)	0.1974 (5)	0.0459 (15)
H1A	0.2050	0.0758	0.1758	0.055*
C2	0.2841 (3)	0.1484 (4)	0.2955 (5)	0.0437 (15)
H2A	0.3182	0.1108	0.2804	0.052*
H2B	0.3001	0.2154	0.3087	0.052*
C3	0.2159 (4)	0.2000 (5)	0.0982 (5)	0.071 (2)
H3A	0.1714	0.1938	0.0368	0.107*
H3B	0.2514	0.1738	0.0782	0.107*
H3C	0.2254	0.2675	0.1173	0.107*
C4	0.0901 (3)	0.1380 (4)	0.1691 (5)	0.0471 (15)
H4A	0.0782	0.1447	0.0905	0.056*
H4B	0.0557	0.1736	0.1857	0.056*
C5	0.0874 (3)	0.0315 (4)	0.1964 (5)	0.0410 (14)
C6	0.0856 (3)	−0.0402 (5)	0.1225 (5)	0.0537 (17)
H6	0.0850	−0.0230	0.0542	0.064*
C7	0.0847 (3)	−0.1367 (5)	0.1488 (7)	0.071 (2)
H7	0.0830	−0.1846	0.0981	0.085*
C8	0.0864 (3)	−0.1628 (5)	0.2511 (7)	0.070 (2)
H8	0.0869	−0.2282	0.2697	0.084*
C9	0.0873 (3)	−0.0925 (5)	0.3243 (6)	0.0627 (19)
H9	0.0877	−0.1097	0.3924	0.075*
C10	0.0877 (3)	0.0050 (5)	0.2968 (5)	0.0471 (15)
H10	0.0882	0.0528	0.3468	0.057*
C11	0.2785 (3)	0.0013 (4)	0.4004 (5)	0.0507 (16)
H11A	0.2485	−0.0240	0.3280	0.061*
H11B	0.2592	−0.0189	0.4521	0.061*
C12	0.3497 (3)	−0.0430 (4)	0.4355 (5)	0.0425 (14)
C13	0.3737 (3)	−0.0720 (4)	0.3563 (5)	0.0493 (16)
H13	0.3454	−0.0641	0.2813	0.059*
C14	0.4395 (3)	−0.1126 (4)	0.3890 (7)	0.0607 (19)
H14	0.4556	−0.1309	0.3361	0.073*
C15	0.4796 (4)	−0.1254 (5)	0.4962 (8)	0.075 (2)
H15	0.5233	−0.1537	0.5173	0.090*
C16	0.4575 (4)	−0.0976 (5)	0.5764 (6)	0.080 (2)
H16	0.4860	−0.1065	0.6511	0.096*
C17	0.3918 (3)	−0.0560 (5)	0.5438 (5)	0.0594 (18)
H17	0.3766	−0.0367	0.5974	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0354 (4)	0.0480 (4)	0.0427 (4)	0.0035 (3)	0.0185 (3)	−0.0051 (4)
Cl1	0.0399 (8)	0.0628 (10)	0.0571 (10)	0.0081 (7)	0.0213 (8)	−0.0107 (8)
Cl2	0.0501 (9)	0.0667 (11)	0.0458 (10)	0.0061 (8)	0.0221 (8)	0.0051 (8)
N1	0.046 (3)	0.038 (3)	0.048 (3)	0.001 (2)	0.025 (2)	0.000 (2)
N2	0.039 (3)	0.038 (3)	0.046 (3)	0.002 (2)	0.016 (2)	−0.002 (2)
C1	0.056 (4)	0.039 (4)	0.050 (4)	−0.003 (3)	0.029 (3)	−0.008 (3)
C2	0.043 (3)	0.037 (4)	0.061 (4)	0.000 (3)	0.032 (3)	−0.004 (3)
C3	0.085 (5)	0.083 (5)	0.067 (5)	0.011 (4)	0.052 (4)	0.017 (4)
C4	0.040 (3)	0.052 (4)	0.043 (4)	0.000 (3)	0.010 (3)	−0.003 (3)
C5	0.030 (3)	0.049 (4)	0.038 (4)	−0.001 (3)	0.008 (3)	−0.006 (3)
C6	0.053 (4)	0.060 (5)	0.058 (4)	−0.007 (3)	0.033 (4)	−0.009 (4)
C7	0.068 (5)	0.051 (5)	0.108 (7)	−0.008 (4)	0.052 (5)	−0.023 (4)
C8	0.059 (4)	0.051 (5)	0.107 (7)	0.000 (4)	0.042 (5)	0.009 (5)
C9	0.059 (4)	0.064 (5)	0.065 (5)	−0.004 (4)	0.026 (4)	0.012 (4)
C10	0.039 (3)	0.059 (4)	0.046 (4)	−0.010 (3)	0.020 (3)	−0.009 (3)
C11	0.047 (4)	0.040 (4)	0.070 (5)	0.002 (3)	0.029 (3)	0.004 (3)
C12	0.043 (3)	0.035 (3)	0.051 (4)	0.004 (3)	0.021 (3)	0.002 (3)
C13	0.055 (4)	0.042 (4)	0.053 (4)	0.001 (3)	0.025 (3)	−0.010 (3)
C14	0.064 (5)	0.044 (4)	0.087 (6)	0.004 (3)	0.044 (5)	−0.012 (4)
C15	0.057 (5)	0.060 (5)	0.106 (7)	0.023 (4)	0.032 (5)	0.005 (5)
C16	0.071 (5)	0.089 (6)	0.059 (5)	0.020 (4)	0.006 (4)	0.016 (4)
C17	0.066 (5)	0.069 (5)	0.044 (4)	0.012 (4)	0.024 (4)	0.004 (3)

Geometric parameters (Å, º) top

Cu1—N1	2.034 (4)	C6—C7	1.373 (8)
Cu1—N2	2.010 (4)	C6—H6	0.9300
Cu1—Cl1	2.2598 (15)	C7—C8	1.388 (10)
Cu1—Cl2	2.2663 (17)	C7—H7	0.9300
Cu1—Cl2ⁱ	2.9858 (18)	C8—C9	1.363 (9)
N1—C4	1.493 (6)	C8—H8	0.9300
N1—C1	1.508 (6)	C9—C10	1.388 (8)
N1—H1	0.9100	C9—H9	0.9300
N2—C2	1.477 (6)	C10—H10	0.9300
N2—C11	1.487 (6)	C11—C12	1.504 (7)
N2—H2	0.9100	C11—H11A	0.9700
C1—C2	1.497 (7)	C11—H11B	0.9700
C1—C3	1.526 (8)	C12—C17	1.352 (8)
C1—H1A	0.9800	C12—C13	1.396 (7)
C2—H2A	0.9700	C13—C14	1.389 (8)
C2—H2B	0.9700	C13—H13	0.9300
C3—H3A	0.9600	C14—C15	1.331 (9)
C3—H3B	0.9600	C14—H14	0.9300
C3—H3C	0.9600	C15—C16	1.378 (10)
C4—C5	1.514 (7)	C15—H15	0.9300
C4—H4A	0.9700	C16—C17	1.393 (8)
C4—H4B	0.9700	C16—H16	0.9300
C5—C10	1.376 (7)	C17—H17	0.9300
C5—C6	1.379 (7)

N2—Cu1—N1	84.19 (18)	C5—C4—H4B	109.2
N2—Cu1—Cl1	174.43 (14)	H4A—C4—H4B	107.9
N1—Cu1—Cl1	92.59 (13)	C10—C5—C6	119.0 (6)
N2—Cu1—Cl2	89.00 (14)	C10—C5—C4	120.1 (5)
N1—Cu1—Cl2	168.46 (14)	C6—C5—C4	120.9 (5)
Cl1—Cu1—Cl2	94.90 (6)	C7—C6—C5	120.6 (6)
N2—Cu1—Cl2ⁱ	88.13 (13)	C7—C6—H6	119.7
N1—Cu1—Cl2ⁱ	88.99 (13)	C5—C6—H6	119.7
Cl1—Cu1—Cl2ⁱ	87.27 (5)	C6—C7—C8	120.0 (7)
Cl2—Cu1—Cl2ⁱ	100.11 (5)	C6—C7—H7	120.0
C4—N1—C1	113.5 (4)	C8—C7—H7	120.0
C4—N1—Cu1	114.8 (3)	C9—C8—C7	119.9 (7)
C1—N1—Cu1	110.9 (3)	C9—C8—H8	120.0
C4—N1—H1	105.6	C7—C8—H8	120.0
C1—N1—H1	105.6	C8—C9—C10	119.8 (7)
Cu1—N1—H1	105.6	C8—C9—H9	120.1
C2—N2—C11	113.8 (4)	C10—C9—H9	120.1
C2—N2—Cu1	105.7 (3)	C5—C10—C9	120.7 (6)
C11—N2—Cu1	115.6 (3)	C5—C10—H10	119.6
C2—N2—H2	107.1	C9—C10—H10	119.6
C11—N2—H2	107.1	N2—C11—C12	113.9 (4)
Cu1—N2—H2	107.1	N2—C11—H11A	108.8
C2—C1—N1	108.0 (4)	C12—C11—H11A	108.8
C2—C1—C3	112.2 (5)	N2—C11—H11B	108.8
N1—C1—C3	112.3 (5)	C12—C11—H11B	108.8
C2—C1—H1A	108.0	H11A—C11—H11B	107.7
N1—C1—H1A	108.0	C17—C12—C13	118.6 (6)
C3—C1—H1A	108.0	C17—C12—C11	121.0 (6)
N2—C2—C1	110.6 (4)	C13—C12—C11	120.4 (6)
N2—C2—H2A	109.5	C14—C13—C12	120.2 (6)
C1—C2—H2A	109.5	C14—C13—H13	119.9
N2—C2—H2B	109.5	C12—C13—H13	119.9
C1—C2—H2B	109.5	C15—C14—C13	120.0 (7)
H2A—C2—H2B	108.1	C15—C14—H14	120.0
C1—C3—H3A	109.5	C13—C14—H14	120.0
C1—C3—H3B	109.5	C14—C15—C16	121.2 (7)
H3A—C3—H3B	109.5	C14—C15—H15	119.4
C1—C3—H3C	109.5	C16—C15—H15	119.4
H3A—C3—H3C	109.5	C15—C16—C17	119.0 (7)
H3B—C3—H3C	109.5	C15—C16—H16	120.5
N1—C4—C5	112.0 (4)	C17—C16—H16	120.5
N1—C4—H4A	109.2	C12—C17—C16	121.1 (6)
C5—C4—H4A	109.2	C12—C17—H17	119.5
N1—C4—H4B	109.2	C16—C17—H17	119.5

N2—Cu1—N1—C4	125.7 (4)	N1—C4—C5—C10	72.6 (6)
Cl1—Cu1—N1—C4	−58.9 (3)	N1—C4—C5—C6	−106.4 (6)
Cl2—Cu1—N1—C4	71.6 (8)	C10—C5—C6—C7	−0.5 (9)
Cl2ⁱ—Cu1—N1—C4	−146.1 (3)	C4—C5—C6—C7	178.5 (5)
N2—Cu1—N1—C1	−4.6 (3)	C5—C6—C7—C8	−0.8 (10)
Cl1—Cu1—N1—C1	170.8 (3)	C6—C7—C8—C9	1.5 (11)
Cl2—Cu1—N1—C1	−58.7 (8)	C7—C8—C9—C10	−1.1 (10)
Cl2ⁱ—Cu1—N1—C1	83.6 (3)	C6—C5—C10—C9	0.9 (9)
N1—Cu1—N2—C2	28.3 (3)	C4—C5—C10—C9	−178.1 (5)
Cl2—Cu1—N2—C2	−161.0 (3)	C8—C9—C10—C5	−0.2 (9)
Cl2ⁱ—Cu1—N2—C2	−60.8 (3)	C2—N2—C11—C12	77.4 (6)
Cl2—Cu1—N2—C11	72.2 (4)	Cu1—N2—C11—C12	−160.0 (4)
Cl2ⁱ—Cu1—N2—C11	172.3 (4)	N2—C11—C12—C17	87.2 (7)
C4—N1—C1—C2	−151.2 (4)	N2—C11—C12—C13	−93.1 (7)
Cu1—N1—C1—C2	−20.1 (5)	C17—C12—C13—C14	−0.4 (9)
C4—N1—C1—C3	84.5 (6)	C11—C12—C13—C14	179.9 (5)
Cu1—N1—C1—C3	−144.4 (4)	C12—C13—C14—C15	1.0 (9)
C11—N2—C2—C1	79.6 (5)	C13—C14—C15—C16	−1.0 (11)
Cu1—N2—C2—C1	−48.4 (5)	C14—C15—C16—C17	0.4 (12)
N1—C1—C2—N2	45.4 (6)	C13—C12—C17—C16	−0.2 (9)
C3—C1—C2—N2	169.7 (5)	C11—C12—C17—C16	179.5 (6)
C1—N1—C4—C5	69.9 (6)	C15—C16—C17—C12	0.2 (11)
Cu1—N1—C4—C5	−59.2 (5)

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl1ⁱ	0.91	2.51	3.386 (5)	161

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂Cl₄(C₁₇H₂₂N₂)₂]
M_r	777.61
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	21.070 (2), 13.7377 (17), 13.2449 (16)
β (°)	114.317 (2)
V (Å³)	3493.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.55
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.746, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	8528, 3077, 1858
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.104, 1.06
No. of reflections	3077
No. of parameters	199
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0084P)² + 19.8791P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.67

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—N1	2.034 (4)	Cu1—Cl2	2.2663 (17)
Cu1—N2	2.010 (4)	Cu1—Cl2ⁱ	2.9858 (18)
Cu1—Cl1	2.2598 (15)

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl1ⁱ	0.91	2.51	3.386 (5)	161.4

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Acknowledgements

We acknowledge the financial support of the Science Foundation of Huaihai Institute of Technology, China.

References

Alves, W. A., Santos, R. H., Paduan-Filho, A., Becerra, C. C., Borin, A. C. & Ferreira, A. M. (2004). Inorg. Chim. Acta, 357, 2269–2278. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Yang, S.-P., Han, L.-J., Xia, H.-T., Wang, D.-Q. & Liu, Y.-F. (2007). Acta Cryst. C63, m610–m614. Web of Science CSD CrossRef IUCr Journals Google Scholar

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