catena-Poly[copper(II)-{μ3-4,4′-dichloro-2,2′-[butane-1,4-diylbis(nitrilo­methanyl­yl­idene)]diphenolato-κ4N,O:N′,O′:O′}]

Kargar, H.; Kia, R.

doi:10.1107/S1600536811009974

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m497-m498

doi:10.1107/S1600536811009974

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catena-Poly[copper(II)-{μ₃-4,4′-dichloro-2,2′-[butane-1,4-diylbis(nitrilomethanylylidene)]diphenolato-κ⁴N,O:N′,O′:O′}]

Hadi Kargar ^a ^* and Reza Kia ^b

^aChemistry Department, Payame Noor University, Tehran 19395-4697, I. R. of Iran, and ^bX-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran
^*Correspondence e-mail: hkargar@pnu.ac.ir

(Received 7 March 2011; accepted 16 March 2011; online 26 March 2011)

The asymmetric unit of the title coordination polymer, [Cu(C₁₈H₁₆Cl₂N₂O₂)]_n, consists of a Schiff base complex in which the Cu^II atom adopts a square-pyramidal coordination geometry, being coordinated by two N and two O atoms of symmetry-related ligands and by a third O atom from a complex related by an inversion center. In the structure, a crystallographic twofold rotation axis bisects the central C—C bonds of the n-butyl spacers of the designated Schiff base ligands, making symmetry-related dimeric units, which are twisted around Cu^II atoms in a bis-bidentate coordination mode. In the crystal, these dimeric units are connected through the third bridging Cu—O bonds [2.3951 (13) Å], forming one-dimensional coordination polymers, which propagate along [001]. Furthermore, intermolecular π–π interactions [centroid–centroid distance = 3.811 (1) Å] stabilize the crystal packing.

Related literature

For van der Waals radii, see: Bondi (1964 ). For background to coordination polymers, see: Kido & Okamoto (2002 ); Li et al. (2006 ); Eddaoudi et al. (2001 ); Dietzel et al. (2005 ). For background to bis-bidentate Schiff base complexes, see: Hannon et al. (1999 ); Lavalette et al. (2003 ). For the synthesis and structural variations of Schiff base complexes, see: Granovski et al. (1993 ); Elmali et al. (2000 ).

Experimental

Crystal data

[Cu(C₁₈H₁₆Cl₂N₂O₂)]
M_r = 426.77
Monoclinic, C 2/c
a = 23.7249 (5) Å
b = 10.5067 (2) Å
c = 15.2460 (3) Å
β = 116.988 (1)°
V = 3386.52 (12) Å³
Z = 8
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 100 K
0.42 × 0.23 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.547, T_max = 0.768
30759 measured reflections
7465 independent reflections
5511 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.108
S = 1.03
7465 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 1.07 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
C18—H18A⋯O1	0.97	2.28	2.973 (2)	127

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009974/su2262sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009974/su2262Isup2.hkl

checkCIF report

Comment top

The design and construction of metal-organic coordination polymers (MOCPs) have attracted considerable attention, not only for their novel topologies but also for their potential in the area of magnetic applications and functional materials (Kido & Okamoto, 2002; Li et al., 2006; Eddaoudi et al., 2001; Dietzel et al., 2005). One of the key strategies in the construction of metal-organic coordination polymers is to select suitable bi- or multi-dentate bridging ligands. Among these, bis-bidentate NN- or NO-donor Schiff base ligands with aliphatic and aromatic spacers (Hannon et al., 1999; Lavalette et al., 2003) have attracted much attention because of the flexibility in their coordination modes and the resulting intermolecular interactions. The long chain aliphatic spacers or rigid aromatic spacers with large bite angles in these ligands favour the bis-bidentate coordination mode and allow the ligands to accomodate metal centers in one unit of the ligand. On the other hand, Schiff bases are one of the most prevalent ligands in coordination chemistry and their complexes are some of the most important stereochemical models in transition metal-organic chemistry, with their ease of preparation and structural variations (Granovski et al., 1993; Elmali et al., 2000).

The molecular structure of the title complex (Fig. 1) consists of symmetry-related dimers in which the Schiff base ligands are twisted around Cu^IIcenters in a bis-bidentate coordination mode, having a crystallographic twofold rotation axis which passes through the central C—C bonds of the n-butyl spacers [C9—C9Aⁱ and C18—C18Aⁱ; symmetry code: (i) -x, y, -z + 1/2 ].

In the crystal the dimer units are connected through Cu—O bonds, forming one-diensional coordination polymer running along the c axis (Fig. 2), in which the Cu^II atom adopts a square-based pyramidal coordination geometry. The Cu^II atoms are supported by the two nitrogen and oxygen atoms of the symmetry-related ligands and a third oxygen atom of neighboring complexes. The lengths of the intermolecular Cu1—O2ⁱ bonds [2.3951 (13) Å; symetry code (i) -x, -y+1, -z] is significantly shorter than the sum of the van der Waals (vdW) radii of these atoms [Cu, 1.43Å and O, 1.52 Å; Bondi, 1964]. There are different non-bonded internuclear Cu···Cu distances. The longer one is separated by the butyl spacers [4.672 Å], and the shorter one is in the centrosymmetric Cu₂O₂ rectangular unit [3.299 Å]. Furthermore, intermolecular π-π interactions stabilize the crystal packings with centroid to centroid distances of 3.811 (1)Å [Cg1 and Cg2 are the centroids of the rings (C1–C6) and (C10–C15)]. There are also C—H···O interactions present (Table 1).

Related literature top

For van der Waals radii, see: Bondi (1964). For background to coordination polymers, see: Kido & Okamoto (2002); Li et al. (2006); Eddaoudi et al. (2001); Dietzel et al. (2005). For background to bis-bidentate Schiff base complexes, see: Hannon et al. (1999); Lavalette et al. (2003). For the synthesis and structural variations of Schiff base complexes, see: Granovski et al. (1993); Elmali et al. (2000).

Experimental top

The title complex was synthesized by the template method of mixing an ethanolic solution (50 ml) of 5-chlorosalicylaldeyde (4 mmol), 1,4-butanediamine (2 mmol), and CuCl₂.4H₂O (2.1 mmol). After stirring at reflux conditions for 2 h, the solution was filtered and the resulting green solid was crystallized from ethanol, giving single crystals suitable for X-ray diffraction. Spectoscopic and analytical data are given in the archived CIF.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title complex, showing 40% probability displacement ellipsoids and the atomic numbering [H-atoms have been omitted for clarity; symmetry code: (A) -x, -y+1, -z].
	Fig. 2. The crystal packing, viewed down the b-axis, of the title complex, showing the one-dimensional coordination chain propagating along the c-axis [H-atoms have been omitted for clarity].

catena-Poly[copper(II)-{µ₃-4,4'-dichloro-2,2'-[butane-1,4- diylbis(nitrilomethanylylidene)]diphenolato- κ⁴N,O:N',O':O'}] top

Crystal data top

[Cu(C₁₈H₁₆Cl₂N₂O₂)]	F(000) = 1736
M_r = 426.77	D_x = 1.674 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7283 reflections
a = 23.7249 (5) Å	θ = 2.4–34.8°
b = 10.5067 (2) Å	µ = 1.62 mm⁻¹
c = 15.2460 (3) Å	T = 100 K
β = 116.988 (1)°	Block, green
V = 3386.52 (12) Å³	0.42 × 0.23 × 0.17 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7465 independent reflections
Radiation source: fine-focus sealed tube	5511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 35.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −38→38
T_min = 0.547, T_max = 0.768	k = −15→16
30759 measured reflections	l = −24→23

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0534P)² + 2.3966P] where P = (F_o² + 2F_c²)/3
7465 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 1.07 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

[Cu(C₁₈H₁₆Cl₂N₂O₂)]	V = 3386.52 (12) Å³
M_r = 426.77	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.7249 (5) Å	µ = 1.62 mm⁻¹
b = 10.5067 (2) Å	T = 100 K
c = 15.2460 (3) Å	0.42 × 0.23 × 0.17 mm
β = 116.988 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7465 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	5511 reflections with I > 2σ(I)
T_min = 0.547, T_max = 0.768	R_int = 0.048
30759 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	Δρ_max = 1.07 e Å⁻³
7465 reflections	Δρ_min = −0.70 e Å⁻³
226 parameters

Special details top

Experimental. Spectoscopic and analytical data:

FTIR (KBr, cm^-1): νmax 1622 (versus), 1533 (s), 1465 (s), 1386 (s), 1317 (s), 1195 (m), 1176 (m), 821 (s), 705 (s). Anal. Calc. for C₁₈H₁₆Cl₂CuN₂O₂: 50.66; H, 3.78; N, 6.56 %. Found: C, 50.70; H, 3.66; N, 6.57 %.

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	0.022690 (9)	0.53850 (2)	0.116076 (15)	0.01452 (6)
Cl1	0.362651 (19)	0.48963 (5)	0.38428 (4)	0.02231 (9)
Cl2	−0.31688 (2)	0.50558 (5)	−0.08067 (4)	0.02457 (10)
O1	0.09481 (6)	0.63334 (13)	0.20125 (10)	0.0197 (2)
O2	−0.04854 (6)	0.44838 (12)	0.01836 (9)	0.0169 (2)
N1	0.06650 (7)	0.37212 (14)	0.17172 (10)	0.0158 (3)
N2	−0.03106 (6)	0.69745 (15)	0.09189 (10)	0.0151 (3)
C1	0.15334 (8)	0.59527 (17)	0.24600 (12)	0.0160 (3)
C2	0.20162 (8)	0.68856 (17)	0.28841 (13)	0.0177 (3)
H2A	0.1904	0.7735	0.2877	0.021*
C3	0.26477 (8)	0.65589 (18)	0.33059 (13)	0.0178 (3)
H3A	0.2956	0.7187	0.3563	0.021*
C4	0.28228 (8)	0.52825 (17)	0.33464 (13)	0.0170 (3)
C5	0.23719 (8)	0.43461 (18)	0.30031 (13)	0.0173 (3)
H5A	0.2495	0.3497	0.3064	0.021*
C6	0.17232 (8)	0.46601 (17)	0.25576 (12)	0.0157 (3)
C7	0.12726 (8)	0.36225 (17)	0.22349 (12)	0.0169 (3)
H7A	0.1435	0.2806	0.2417	0.020*
C8	0.02982 (8)	0.25245 (18)	0.14935 (13)	0.0175 (3)
H8A	0.0587	0.1812	0.1749	0.021*
H8B	0.0064	0.2424	0.0785	0.021*
C9	−0.01643 (8)	0.25036 (18)	0.19396 (12)	0.0176 (3)
H9A	−0.0438	0.3242	0.1709	0.021*
H9B	−0.0428	0.1751	0.1709	0.021*
C10	−0.10753 (8)	0.46309 (17)	0.00258 (12)	0.0150 (3)
C11	−0.14972 (8)	0.35895 (18)	−0.03223 (13)	0.0189 (3)
H11A	−0.1347	0.2802	−0.0402	0.023*
C12	−0.21273 (8)	0.37172 (19)	−0.05460 (13)	0.0197 (3)
H12A	−0.2396	0.3018	−0.0766	0.024*
C13	−0.23591 (8)	0.48954 (19)	−0.04415 (13)	0.0180 (3)
C14	−0.19608 (8)	0.59274 (18)	−0.00739 (12)	0.0170 (3)
H14A	−0.2119	0.6704	0.0009	0.020*
C15	−0.13129 (7)	0.58023 (17)	0.01757 (12)	0.0151 (3)
C16	−0.09196 (8)	0.69309 (17)	0.05320 (12)	0.0155 (3)
H16A	−0.1128	0.7699	0.0475	0.019*
C17	−0.00209 (8)	0.82531 (17)	0.12060 (12)	0.0167 (3)
H17A	−0.0338	0.8894	0.0852	0.020*
H17B	0.0315	0.8335	0.1015	0.020*
C18	0.02494 (8)	0.85016 (17)	0.23129 (12)	0.0161 (3)
H18A	0.0563	0.7854	0.2665	0.019*
H18B	0.0463	0.9319	0.2462	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01204 (9)	0.01378 (10)	0.01660 (10)	0.00038 (7)	0.00551 (7)	−0.00146 (7)
Cl1	0.01324 (16)	0.0221 (2)	0.0287 (2)	0.00137 (15)	0.00701 (15)	0.00028 (16)
Cl2	0.01322 (17)	0.0314 (3)	0.0279 (2)	−0.00119 (16)	0.00826 (16)	−0.00369 (18)
O1	0.0139 (5)	0.0149 (6)	0.0256 (6)	0.0014 (4)	0.0048 (5)	−0.0040 (5)
O2	0.0132 (5)	0.0174 (6)	0.0205 (5)	−0.0002 (4)	0.0079 (4)	−0.0032 (4)
N1	0.0160 (6)	0.0149 (7)	0.0179 (6)	0.0002 (5)	0.0089 (5)	−0.0007 (5)
N2	0.0155 (6)	0.0150 (7)	0.0148 (6)	−0.0003 (5)	0.0068 (5)	−0.0005 (5)
C1	0.0149 (7)	0.0162 (8)	0.0169 (7)	0.0012 (6)	0.0074 (6)	−0.0015 (6)
C2	0.0167 (7)	0.0139 (8)	0.0205 (7)	0.0006 (6)	0.0066 (6)	−0.0014 (6)
C3	0.0165 (7)	0.0171 (8)	0.0184 (7)	−0.0019 (6)	0.0066 (6)	−0.0016 (6)
C4	0.0133 (6)	0.0179 (8)	0.0180 (7)	0.0010 (6)	0.0055 (6)	−0.0005 (6)
C5	0.0158 (7)	0.0158 (8)	0.0197 (7)	0.0014 (6)	0.0075 (6)	0.0011 (6)
C6	0.0161 (7)	0.0148 (8)	0.0168 (7)	−0.0003 (6)	0.0079 (6)	−0.0002 (6)
C7	0.0165 (7)	0.0159 (8)	0.0187 (7)	0.0018 (6)	0.0084 (6)	−0.0001 (6)
C8	0.0173 (7)	0.0164 (8)	0.0213 (7)	−0.0021 (6)	0.0108 (6)	−0.0024 (6)
C9	0.0170 (7)	0.0177 (8)	0.0191 (7)	−0.0019 (6)	0.0090 (6)	−0.0008 (6)
C10	0.0144 (6)	0.0158 (8)	0.0150 (6)	0.0008 (5)	0.0067 (5)	−0.0004 (6)
C11	0.0165 (7)	0.0176 (8)	0.0218 (8)	−0.0010 (6)	0.0080 (6)	−0.0034 (6)
C12	0.0176 (7)	0.0208 (9)	0.0205 (7)	−0.0044 (6)	0.0085 (6)	−0.0032 (6)
C13	0.0133 (7)	0.0234 (9)	0.0171 (7)	−0.0011 (6)	0.0066 (6)	−0.0007 (6)
C14	0.0142 (7)	0.0190 (8)	0.0172 (7)	0.0028 (6)	0.0065 (6)	0.0000 (6)
C15	0.0137 (6)	0.0161 (8)	0.0146 (6)	−0.0004 (5)	0.0057 (5)	−0.0007 (6)
C16	0.0147 (7)	0.0150 (8)	0.0154 (7)	0.0019 (5)	0.0057 (5)	−0.0005 (5)
C17	0.0177 (7)	0.0142 (8)	0.0174 (7)	−0.0012 (6)	0.0075 (6)	0.0008 (6)
C18	0.0143 (7)	0.0151 (8)	0.0178 (7)	−0.0013 (6)	0.0063 (5)	−0.0012 (6)

Geometric parameters (Å, º) top

Cu1—O1	1.8948 (13)	C7—H7A	0.9300
Cu1—O2	1.9201 (12)	C8—C9	1.531 (2)
Cu1—N1	2.0139 (15)	C8—H8A	0.9700
Cu1—N2	2.0308 (15)	C8—H8B	0.9700
Cu1—O2ⁱ	2.3951 (13)	C9—C9ⁱⁱ	1.523 (3)
Cl1—C4	1.7503 (17)	C9—H9A	0.9700
Cl2—C13	1.7488 (17)	C9—H9B	0.9700
O1—C1	1.301 (2)	C10—C11	1.414 (2)
O2—C10	1.3172 (19)	C10—C15	1.415 (2)
O2—Cu1ⁱ	2.3951 (13)	C11—C12	1.381 (2)
N1—C7	1.296 (2)	C11—H11A	0.9300
N1—C8	1.478 (2)	C12—C13	1.393 (3)
N2—C16	1.290 (2)	C12—H12A	0.9300
N2—C17	1.482 (2)	C13—C14	1.379 (3)
C1—C6	1.417 (3)	C14—C15	1.412 (2)
C1—C2	1.421 (2)	C14—H14A	0.9300
C2—C3	1.379 (2)	C15—C16	1.453 (2)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.397 (3)	C17—C18	1.531 (2)
C3—H3A	0.9300	C17—H17A	0.9700
C4—C5	1.370 (2)	C17—H17B	0.9700
C5—C6	1.411 (2)	C18—C18ⁱⁱ	1.529 (3)
C5—H5A	0.9300	C18—H18A	0.9700
C6—C7	1.448 (2)	C18—H18B	0.9700

O1—Cu1—O2	173.80 (6)	C9—C8—H8A	109.2
O1—Cu1—N1	92.00 (6)	N1—C8—H8B	109.2
O2—Cu1—N1	90.18 (6)	C9—C8—H8B	109.2
O1—Cu1—N2	89.39 (6)	H8A—C8—H8B	107.9
O2—Cu1—N2	90.32 (6)	C9ⁱⁱ—C9—C8	113.17 (17)
N1—Cu1—N2	162.14 (6)	C9ⁱⁱ—C9—H9A	108.9
O1—Cu1—O2ⁱ	93.09 (5)	C8—C9—H9A	108.9
O2—Cu1—O2ⁱ	80.87 (5)	C9ⁱⁱ—C9—H9B	108.9
N1—Cu1—O2ⁱ	97.28 (5)	C8—C9—H9B	108.9
N2—Cu1—O2ⁱ	100.42 (5)	H9A—C9—H9B	107.8
C1—O1—Cu1	127.92 (12)	O2—C10—C11	119.37 (15)
C10—O2—Cu1	124.88 (11)	O2—C10—C15	122.73 (15)
C10—O2—Cu1ⁱ	120.03 (10)	C11—C10—C15	117.89 (15)
Cu1—O2—Cu1ⁱ	99.13 (5)	C12—C11—C10	121.35 (17)
C7—N1—C8	116.63 (15)	C12—C11—H11A	119.3
C7—N1—Cu1	123.02 (13)	C10—C11—H11A	119.3
C8—N1—Cu1	120.25 (11)	C11—C12—C13	119.84 (17)
C16—N2—C17	116.13 (15)	C11—C12—H12A	120.1
C16—N2—Cu1	122.32 (12)	C13—C12—H12A	120.1
C17—N2—Cu1	121.53 (10)	C14—C13—C12	120.80 (15)
O1—C1—C6	124.21 (16)	C14—C13—Cl2	120.31 (14)
O1—C1—C2	118.33 (16)	C12—C13—Cl2	118.88 (14)
C6—C1—C2	117.46 (15)	C13—C14—C15	119.85 (16)
C3—C2—C1	121.43 (17)	C13—C14—H14A	120.1
C3—C2—H2A	119.3	C15—C14—H14A	120.1
C1—C2—H2A	119.3	C14—C15—C10	120.14 (16)
C2—C3—C4	119.86 (16)	C14—C15—C16	117.42 (16)
C2—C3—H3A	120.1	C10—C15—C16	122.34 (14)
C4—C3—H3A	120.1	N2—C16—C15	126.57 (16)
C5—C4—C3	120.49 (16)	N2—C16—H16A	116.7
C5—C4—Cl1	120.47 (14)	C15—C16—H16A	116.7
C3—C4—Cl1	119.04 (13)	N2—C17—C18	112.71 (14)
C4—C5—C6	120.53 (17)	N2—C17—H17A	109.0
C4—C5—H5A	119.7	C18—C17—H17A	109.0
C6—C5—H5A	119.7	N2—C17—H17B	109.0
C5—C6—C1	120.00 (16)	C18—C17—H17B	109.0
C5—C6—C7	117.61 (16)	H17A—C17—H17B	107.8
C1—C6—C7	122.37 (15)	C18ⁱⁱ—C18—C17	113.78 (17)
N1—C7—C6	126.34 (17)	C18ⁱⁱ—C18—H18A	108.8
N1—C7—H7A	116.8	C17—C18—H18A	108.8
C6—C7—H7A	116.8	C18ⁱⁱ—C18—H18B	108.8
N1—C8—C9	112.04 (14)	C17—C18—H18B	108.8
N1—C8—H8A	109.2	H18A—C18—H18B	107.7

N1—Cu1—O1—C1	21.62 (15)	O1—C1—C6—C5	176.08 (16)
N2—Cu1—O1—C1	−176.19 (15)	C2—C1—C6—C5	−4.2 (2)
O2ⁱ—Cu1—O1—C1	−75.79 (15)	O1—C1—C6—C7	−5.4 (3)
N1—Cu1—O2—C10	125.77 (14)	C2—C1—C6—C7	174.30 (16)
N2—Cu1—O2—C10	−36.38 (14)	C8—N1—C7—C6	−178.71 (15)
O2ⁱ—Cu1—O2—C10	−136.88 (16)	Cu1—N1—C7—C6	4.9 (2)
N1—Cu1—O2—Cu1ⁱ	−97.35 (5)	C5—C6—C7—N1	−171.74 (16)
N2—Cu1—O2—Cu1ⁱ	100.50 (5)	C1—C6—C7—N1	9.7 (3)
O2ⁱ—Cu1—O2—Cu1ⁱ	0.0	C7—N1—C8—C9	117.57 (17)
O1—Cu1—N1—C7	−16.53 (14)	Cu1—N1—C8—C9	−65.94 (17)
O2—Cu1—N1—C7	157.66 (14)	N1—C8—C9—C9ⁱⁱ	−65.42 (14)
N2—Cu1—N1—C7	−110.7 (2)	Cu1—O2—C10—C11	−149.56 (13)
O2ⁱ—Cu1—N1—C7	76.84 (14)	Cu1ⁱ—O2—C10—C11	81.66 (18)
O1—Cu1—N1—C8	167.21 (12)	Cu1—O2—C10—C15	31.4 (2)
O2—Cu1—N1—C8	−18.60 (12)	Cu1ⁱ—O2—C10—C15	−97.34 (16)
N2—Cu1—N1—C8	73.0 (2)	O2—C10—C11—C12	−176.62 (16)
O2ⁱ—Cu1—N1—C8	−99.42 (12)	C15—C10—C11—C12	2.4 (3)
O1—Cu1—N2—C16	−164.27 (14)	C10—C11—C12—C13	0.8 (3)
O2—Cu1—N2—C16	21.92 (14)	C11—C12—C13—C14	−3.0 (3)
N1—Cu1—N2—C16	−69.7 (2)	C11—C12—C13—Cl2	175.83 (14)
O2ⁱ—Cu1—N2—C16	102.69 (13)	C12—C13—C14—C15	1.7 (3)
O1—Cu1—N2—C17	13.94 (12)	Cl2—C13—C14—C15	−177.05 (13)
O2—Cu1—N2—C17	−159.87 (12)	C13—C14—C15—C10	1.6 (2)
N1—Cu1—N2—C17	108.6 (2)	C13—C14—C15—C16	178.22 (16)
O2ⁱ—Cu1—N2—C17	−79.09 (12)	O2—C10—C15—C14	175.38 (15)
Cu1—O1—C1—C6	−14.3 (2)	C11—C10—C15—C14	−3.6 (2)
Cu1—O1—C1—C2	166.02 (12)	O2—C10—C15—C16	−1.0 (3)
O1—C1—C2—C3	−175.20 (16)	C11—C10—C15—C16	179.95 (16)
C6—C1—C2—C3	5.1 (2)	C17—N2—C16—C15	178.78 (15)
C1—C2—C3—C4	−1.8 (3)	Cu1—N2—C16—C15	−2.9 (2)
C2—C3—C4—C5	−2.4 (3)	C14—C15—C16—N2	169.93 (16)
C2—C3—C4—Cl1	177.60 (14)	C10—C15—C16—N2	−13.6 (3)
C3—C4—C5—C6	3.3 (3)	C16—N2—C17—C18	101.27 (17)
Cl1—C4—C5—C6	−176.79 (13)	Cu1—N2—C17—C18	−77.05 (16)
C4—C5—C6—C1	0.2 (3)	N2—C17—C18—C18ⁱⁱ	−63.30 (14)
C4—C5—C6—C7	−178.41 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O1	0.97	2.28	2.973 (2)	127

Experimental details

Crystal data
Chemical formula	[Cu(C₁₈H₁₆Cl₂N₂O₂)]
M_r	426.77
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	23.7249 (5), 10.5067 (2), 15.2460 (3)
β (°)	116.988 (1)
V (Å³)	3386.52 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.42 × 0.23 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.547, 0.768
No. of measured, independent and observed [I > 2σ(I)] reflections	30759, 7465, 5511
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.810

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.108, 1.03
No. of reflections	7465
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.07, −0.70

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O1	0.97	2.28	2.973 (2)	127

Acknowledgements

HK thanks PNU for support of this work. RK thanks the Science and Research Branch, Islamic Azad University.

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