{4,4′,6,6′-Tetra­chloro-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methanylyl­idene)]}copper(II)

Kargar, H.; Kia, R.; Abbasian, S.; Tahir, M.N.

doi:10.1107/S160053681200195X

{4,4′,6,6′-Tetrachloro-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]}copper(II)

H. Kargar, R. Kia, S. Abbasian and M. N. Tahir

In the title Schiff base complex, [Cu(C₁₉H₁₆Cl₄N₂O₂)], the geometry around the Cu^II atom is distorted square-planar defined by the N₂O₂ donor atoms of the coordinated ligand. The dihedral angle between the substituted benzene rings is 29.95 (16)°. In the crystal, molecules are linked along the b axis, forming individual dimers through C—H

O interactions. The crystal structure is further stabilized by intermolecular π–π interactions [centroid–centroid distance = 3.6131 (17) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681200195X/hp2025sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053681200195X/hp2025Isup2.hkl Contains datablock I

CCDC reference: 867990

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.005 Å
R factor = 0.047
wR factor = 0.105
Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          8

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c   .......      P21/n

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

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

Comment top

Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with the ease of preparation and structural variations (Granovski et al., 1993; Blower et al., (1998). In continuation of our work on the crystal structure of Schiff base metal complexes (Kargar et al., 2012; Kargar et al., 2011; Ghaemi, et al., (2011), we determined the X-ray structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a Schiff base complex. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structure (Kargar et al., 2012; Kargar et al., 2011; Ghaemi, et al., (2011).

The geometry around Cu^II is a distorted square-planar which is supported by the N₂O₂ donor atoms of the coordinated Schiff base ligand. The dihedral angle between the substituted benzene rings is 29.95 (16)°. In the crystal structure the molecules are linked together along the b-axis, forming individual dimers through the intermolecular C—H···O interactions (Table 1, Fig. 2). The crystal structure is further stabilized by the intermolecular π-π interaction [Cg1···Cg1ⁱⁱ = 3.6131 (17)Å; (ii) 1 - X, 1- Y,-Z; Cg1 is the centroid of Cu(1)/O(2)/C(19)/C(14)/C(13)/N(2) ring].

Related literature top

For standard values of bond lengths, see: Allen et al. (1987). For applications of Schiff bases in coordination chemistry, see, for example: Granovski et al. (1993); Blower (1998). For related structures see, for example: Ghaemi et al. (2011); Kargar et al. (2011, 2012).

Experimental top

The title compound was synthesized by adding 3,5-dichloro-salicylaldehyde-2,2-dimethyl-1, 3-propanediamine (2 mmol) to a solution of CuCl₂. 4H₂O (2.1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant solution was filtered. Dark-green single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The ORTEP plot of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. A part of the packing diagram of the title compound showing individual dimer formation through the intermolecular C—H···O intearctions (dashed lines). Only the H atoms involved in the interactions are shown.

{4,4',6,6'-Tetrachloro-2,2'-[2,2-dimethylpropane-1,3- diylbis(nitrilomethanylylidene)]}copper(II) top

Crystal data top

[Cu(C₁₉H₁₆Cl₄N₂O₂)]	F(000) = 1028
M_r = 509.68	D_x = 1.625 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2540 reflections
a = 12.4002 (10) Å	θ = 2.5–27.4°
b = 8.4570 (7) Å	µ = 1.58 mm⁻¹
c = 20.0316 (19) Å	T = 291 K
β = 97.278 (4)°	Block, dark-green
V = 2083.8 (3) Å³	0.25 × 0.18 × 0.09 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4988 independent reflections
Radiation source: fine-focus sealed tube	2882 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→14
T_min = 0.694, T_max = 0.871	k = −9→11
18291 measured reflections	l = −26→26

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0376P)²] where P = (F_o² + 2F_c²)/3
4988 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cu(C₁₉H₁₆Cl₄N₂O₂)]	V = 2083.8 (3) Å³
M_r = 509.68	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.4002 (10) Å	µ = 1.58 mm⁻¹
b = 8.4570 (7) Å	T = 291 K
c = 20.0316 (19) Å	0.25 × 0.18 × 0.09 mm
β = 97.278 (4)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4988 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2882 reflections with I > 2σ(I)
T_min = 0.694, T_max = 0.871	R_int = 0.060
18291 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.00	Δρ_max = 0.38 e Å⁻³
4988 reflections	Δρ_min = −0.36 e Å⁻³
255 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.5462 (3)	0.8875 (4)	0.14363 (17)	0.0370 (8)
C2	0.6238 (3)	0.9020 (4)	0.20186 (18)	0.0428 (9)
C3	0.6049 (3)	0.9834 (4)	0.25795 (18)	0.0468 (9)
H3	0.6577	0.9874	0.2953	0.056*
C4	0.5058 (3)	1.0605 (4)	0.25883 (18)	0.0486 (9)
C5	0.4286 (3)	1.0532 (4)	0.20422 (18)	0.0430 (9)
H5	0.3629	1.1057	0.2051	0.052*
C6	0.4466 (3)	0.9681 (4)	0.14670 (17)	0.0365 (8)
C7	0.3634 (3)	0.9733 (4)	0.08983 (17)	0.0398 (8)
H7	0.3024	1.0343	0.0944	0.048*
C8	0.2764 (3)	0.9331 (4)	−0.02093 (17)	0.0442 (9)
H8A	0.3077	0.9657	−0.0607	0.053*
H8B	0.2327	1.0201	−0.0078	0.053*
C9	0.2022 (3)	0.7905 (4)	−0.03888 (18)	0.0414 (8)
C10	0.1184 (3)	0.7758 (5)	0.0105 (2)	0.0725 (13)
H10A	0.1548	0.7761	0.0557	0.109*
H10B	0.0788	0.6788	0.0022	0.109*
H10C	0.0689	0.8634	0.0045	0.109*
C11	0.1447 (3)	0.8178 (5)	−0.1105 (2)	0.0722 (13)
H11A	0.0918	0.7361	−0.1217	0.108*
H11B	0.1973	0.8156	−0.1418	0.108*
H11C	0.1091	0.9188	−0.1127	0.108*
C12	0.2678 (2)	0.6363 (4)	−0.03537 (18)	0.0436 (9)
H12A	0.2730	0.5953	0.0101	0.052*
H12B	0.2283	0.5593	−0.0649	0.052*
C13	0.4035 (3)	0.5747 (4)	−0.10521 (18)	0.0411 (9)
H13	0.3483	0.5186	−0.1305	0.049*
C14	0.5102 (3)	0.5676 (4)	−0.12688 (18)	0.0394 (8)
C15	0.5173 (3)	0.4938 (4)	−0.18871 (19)	0.0490 (10)
H15	0.4548	0.4545	−0.2138	0.059*
C16	0.6153 (3)	0.4793 (4)	−0.21236 (18)	0.0505 (10)
C17	0.7093 (3)	0.5351 (4)	−0.17506 (18)	0.0464 (9)
H17	0.7761	0.5236	−0.1910	0.056*
C18	0.7030 (2)	0.6076 (4)	−0.11442 (17)	0.0374 (8)
C19	0.6035 (2)	0.6294 (4)	−0.08710 (17)	0.0354 (8)
Cl1	0.74867 (8)	0.80938 (13)	0.20120 (6)	0.0735 (4)
Cl2	0.48425 (9)	1.16671 (15)	0.33020 (6)	0.0774 (4)
Cl3	0.62354 (9)	0.38486 (16)	−0.28877 (6)	0.0822 (4)
Cl4	0.82198 (6)	0.67591 (10)	−0.06837 (5)	0.0476 (2)
Cu1	0.48016 (3)	0.76529 (5)	0.01057 (2)	0.03872 (14)
N1	0.3649 (2)	0.9025 (3)	0.03362 (14)	0.0384 (7)
N2	0.37799 (19)	0.6517 (3)	−0.05406 (14)	0.0374 (7)
O1	0.57082 (17)	0.8082 (3)	0.09215 (12)	0.0448 (6)
O2	0.60372 (17)	0.6982 (3)	−0.02938 (12)	0.0431 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0357 (19)	0.035 (2)	0.040 (2)	−0.0035 (15)	0.0030 (16)	0.0027 (16)
C2	0.0335 (19)	0.038 (2)	0.055 (2)	0.0000 (15)	−0.0015 (17)	0.0029 (18)
C3	0.048 (2)	0.045 (2)	0.045 (2)	−0.0118 (17)	−0.0026 (18)	0.0024 (18)
C4	0.050 (2)	0.054 (2)	0.042 (2)	−0.0112 (19)	0.0095 (19)	−0.0025 (18)
C5	0.040 (2)	0.045 (2)	0.045 (2)	0.0019 (17)	0.0106 (18)	0.0005 (18)
C6	0.0335 (19)	0.036 (2)	0.040 (2)	−0.0006 (15)	0.0041 (16)	0.0032 (16)
C7	0.0345 (19)	0.037 (2)	0.049 (2)	0.0021 (15)	0.0108 (17)	0.0023 (17)
C8	0.046 (2)	0.045 (2)	0.040 (2)	0.0141 (17)	−0.0017 (17)	0.0079 (17)
C9	0.0311 (18)	0.047 (2)	0.046 (2)	0.0060 (15)	0.0005 (16)	0.0039 (17)
C10	0.044 (2)	0.084 (3)	0.094 (4)	0.007 (2)	0.028 (2)	−0.004 (3)
C11	0.070 (3)	0.067 (3)	0.070 (3)	0.010 (2)	−0.027 (2)	−0.001 (2)
C12	0.0301 (18)	0.046 (2)	0.055 (2)	−0.0014 (16)	0.0085 (17)	0.0046 (18)
C13	0.0324 (19)	0.036 (2)	0.053 (2)	−0.0017 (15)	−0.0012 (17)	0.0003 (17)
C14	0.0326 (19)	0.036 (2)	0.049 (2)	0.0016 (15)	0.0036 (17)	−0.0009 (17)
C15	0.040 (2)	0.051 (2)	0.055 (3)	−0.0033 (17)	0.0005 (19)	−0.0141 (19)
C16	0.044 (2)	0.057 (2)	0.052 (3)	−0.0002 (18)	0.0116 (19)	−0.018 (2)
C17	0.039 (2)	0.048 (2)	0.056 (2)	0.0011 (17)	0.0177 (19)	−0.0066 (19)
C18	0.0329 (18)	0.0348 (19)	0.045 (2)	−0.0006 (14)	0.0066 (16)	0.0010 (16)
C19	0.0337 (19)	0.0294 (18)	0.043 (2)	0.0025 (14)	0.0034 (16)	0.0011 (16)
Cl1	0.0471 (6)	0.0767 (8)	0.0895 (9)	0.0202 (5)	−0.0185 (6)	−0.0163 (6)
Cl2	0.0730 (8)	0.1044 (9)	0.0569 (7)	−0.0119 (7)	0.0172 (6)	−0.0287 (6)
Cl3	0.0600 (7)	0.1171 (10)	0.0709 (8)	−0.0016 (6)	0.0130 (6)	−0.0493 (7)
Cl4	0.0320 (5)	0.0540 (6)	0.0568 (6)	−0.0024 (4)	0.0058 (4)	−0.0025 (5)
Cu1	0.0315 (2)	0.0416 (3)	0.0435 (3)	0.00221 (18)	0.00652 (19)	−0.0001 (2)
N1	0.0312 (15)	0.0406 (17)	0.0418 (18)	0.0036 (12)	−0.0011 (13)	0.0022 (14)
N2	0.0293 (15)	0.0356 (16)	0.0481 (18)	−0.0012 (12)	0.0086 (13)	0.0008 (14)
O1	0.0317 (13)	0.0533 (15)	0.0483 (16)	0.0058 (11)	0.0006 (11)	−0.0046 (12)
O2	0.0321 (13)	0.0509 (15)	0.0469 (15)	−0.0002 (10)	0.0073 (11)	−0.0083 (12)

Geometric parameters (Å, º) top

C1—O1	1.299 (4)	C11—H11A	0.9600
C1—C6	1.418 (4)	C11—H11B	0.9600
C1—C2	1.420 (4)	C11—H11C	0.9600
C2—C3	1.362 (5)	C12—N2	1.467 (4)
C2—Cl1	1.737 (3)	C12—H12A	0.9700
C3—C4	1.394 (5)	C12—H12B	0.9700
C3—H3	0.9300	C13—N2	1.287 (4)
C4—C5	1.360 (5)	C13—C14	1.444 (4)
C4—Cl2	1.737 (4)	C13—H13	0.9300
C5—C6	1.400 (4)	C14—C15	1.399 (5)
C5—H5	0.9300	C14—C19	1.419 (4)
C6—C7	1.437 (4)	C15—C16	1.365 (4)
C7—N1	1.278 (4)	C15—H15	0.9300
C7—H7	0.9300	C16—C17	1.385 (5)
C8—N1	1.470 (4)	C16—Cl3	1.741 (3)
C8—C9	1.532 (4)	C17—C18	1.372 (4)
C8—H8A	0.9700	C17—H17	0.9300
C8—H8B	0.9700	C18—C19	1.424 (4)
C9—C10	1.528 (5)	C18—Cl4	1.737 (3)
C9—C12	1.534 (4)	C19—O2	1.294 (4)
C9—C11	1.537 (5)	Cu1—O1	1.898 (2)
C10—H10A	0.9600	Cu1—O2	1.903 (2)
C10—H10B	0.9600	Cu1—N1	1.942 (3)
C10—H10C	0.9600	Cu1—N2	1.947 (3)

O1—C1—C6	125.2 (3)	H11A—C11—H11C	109.5
O1—C1—C2	119.6 (3)	H11B—C11—H11C	109.5
C6—C1—C2	115.2 (3)	N2—C12—C9	114.7 (3)
C3—C2—C1	123.5 (3)	N2—C12—H12A	108.6
C3—C2—Cl1	118.7 (3)	C9—C12—H12A	108.6
C1—C2—Cl1	117.8 (3)	N2—C12—H12B	108.6
C2—C3—C4	119.3 (3)	C9—C12—H12B	108.6
C2—C3—H3	120.3	H12A—C12—H12B	107.6
C4—C3—H3	120.3	N2—C13—C14	126.0 (3)
C5—C4—C3	120.0 (3)	N2—C13—H13	117.0
C5—C4—Cl2	121.3 (3)	C14—C13—H13	117.0
C3—C4—Cl2	118.7 (3)	C15—C14—C19	121.5 (3)
C4—C5—C6	121.1 (3)	C15—C14—C13	116.6 (3)
C4—C5—H5	119.5	C19—C14—C13	121.9 (3)
C6—C5—H5	119.5	C16—C15—C14	120.4 (3)
C5—C6—C1	120.8 (3)	C16—C15—H15	119.8
C5—C6—C7	117.6 (3)	C14—C15—H15	119.8
C1—C6—C7	121.5 (3)	C15—C16—C17	120.5 (3)
N1—C7—C6	126.5 (3)	C15—C16—Cl3	120.0 (3)
N1—C7—H7	116.7	C17—C16—Cl3	119.5 (3)
C6—C7—H7	116.7	C18—C17—C16	119.4 (3)
N1—C8—C9	113.9 (3)	C18—C17—H17	120.3
N1—C8—H8A	108.8	C16—C17—H17	120.3
C9—C8—H8A	108.8	C17—C18—C19	123.2 (3)
N1—C8—H8B	108.8	C17—C18—Cl4	118.6 (2)
C9—C8—H8B	108.8	C19—C18—Cl4	118.2 (3)
H8A—C8—H8B	107.7	O2—C19—C14	125.2 (3)
C10—C9—C8	110.5 (3)	O2—C19—C18	119.9 (3)
C10—C9—C12	107.6 (3)	C14—C19—C18	114.9 (3)
C8—C9—C12	111.1 (3)	O1—Cu1—O2	89.91 (10)
C10—C9—C11	110.1 (3)	O1—Cu1—N1	93.14 (11)
C8—C9—C11	107.1 (3)	O2—Cu1—N1	159.14 (11)
C12—C9—C11	110.6 (3)	O1—Cu1—N2	158.73 (10)
C9—C10—H10A	109.5	O2—Cu1—N2	93.67 (10)
C9—C10—H10B	109.5	N1—Cu1—N2	90.94 (11)
H10A—C10—H10B	109.5	C7—N1—C8	118.7 (3)
C9—C10—H10C	109.5	C7—N1—Cu1	125.7 (2)
H10A—C10—H10C	109.5	C8—N1—Cu1	115.6 (2)
H10B—C10—H10C	109.5	C13—N2—C12	119.3 (3)
C9—C11—H11A	109.5	C13—N2—Cu1	125.0 (2)
C9—C11—H11B	109.5	C12—N2—Cu1	115.0 (2)
H11A—C11—H11B	109.5	C1—O1—Cu1	127.5 (2)
C9—C11—H11C	109.5	C19—O2—Cu1	126.8 (2)

O1—C1—C2—C3	179.8 (3)	C15—C14—C19—C18	−1.1 (5)
C6—C1—C2—C3	1.6 (5)	C13—C14—C19—C18	177.7 (3)
O1—C1—C2—Cl1	−0.7 (4)	C17—C18—C19—O2	179.7 (3)
C6—C1—C2—Cl1	−178.9 (2)	Cl4—C18—C19—O2	−0.1 (4)
C1—C2—C3—C4	−1.5 (5)	C17—C18—C19—C14	1.1 (5)
Cl1—C2—C3—C4	179.0 (3)	Cl4—C18—C19—C14	−178.7 (2)
C2—C3—C4—C5	0.4 (5)	C6—C7—N1—C8	−174.7 (3)
C2—C3—C4—Cl2	−178.8 (3)	C6—C7—N1—Cu1	1.0 (5)
C3—C4—C5—C6	0.5 (5)	C9—C8—N1—C7	−112.5 (3)
Cl2—C4—C5—C6	179.7 (3)	C9—C8—N1—Cu1	71.4 (3)
C4—C5—C6—C1	−0.3 (5)	O1—Cu1—N1—C7	−5.6 (3)
C4—C5—C6—C7	−176.7 (3)	O2—Cu1—N1—C7	−103.6 (4)
O1—C1—C6—C5	−178.7 (3)	N2—Cu1—N1—C7	153.5 (3)
C2—C1—C6—C5	−0.6 (5)	O1—Cu1—N1—C8	170.2 (2)
O1—C1—C6—C7	−2.5 (5)	O2—Cu1—N1—C8	72.2 (4)
C2—C1—C6—C7	175.6 (3)	N2—Cu1—N1—C8	−30.7 (2)
C5—C6—C7—N1	−179.3 (3)	C14—C13—N2—C12	−174.9 (3)
C1—C6—C7—N1	4.3 (5)	C14—C13—N2—Cu1	−4.7 (5)
N1—C8—C9—C10	81.1 (4)	C9—C12—N2—C13	−118.0 (3)
N1—C8—C9—C12	−38.1 (4)	C9—C12—N2—Cu1	70.9 (3)
N1—C8—C9—C11	−159.0 (3)	O1—Cu1—N2—C13	−103.4 (3)
C10—C9—C12—N2	−153.9 (3)	O2—Cu1—N2—C13	−4.1 (3)
C8—C9—C12—N2	−33.0 (4)	N1—Cu1—N2—C13	155.5 (3)
C11—C9—C12—N2	85.8 (4)	O1—Cu1—N2—C12	67.2 (4)
N2—C13—C14—C15	−172.0 (3)	O2—Cu1—N2—C12	166.4 (2)
N2—C13—C14—C19	9.1 (5)	N1—Cu1—N2—C12	−33.9 (2)
C19—C14—C15—C16	0.1 (5)	C6—C1—O1—Cu1	−4.6 (5)
C13—C14—C15—C16	−178.7 (3)	C2—C1—O1—Cu1	177.4 (2)
C14—C15—C16—C17	1.0 (6)	O2—Cu1—O1—C1	166.7 (3)
C14—C15—C16—Cl3	179.1 (3)	N1—Cu1—O1—C1	7.4 (3)
C15—C16—C17—C18	−1.0 (6)	N2—Cu1—O1—C1	−93.3 (4)
Cl3—C16—C17—C18	−179.1 (3)	C14—C19—O2—Cu1	−10.9 (5)
C16—C17—C18—C19	−0.1 (5)	C18—C19—O2—Cu1	170.7 (2)
C16—C17—C18—Cl4	179.7 (3)	O1—Cu1—O2—C19	170.8 (3)
C15—C14—C19—O2	−179.6 (3)	N1—Cu1—O2—C19	−90.6 (4)
C13—C14—C19—O2	−0.8 (5)	N2—Cu1—O2—C19	11.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ⁱ	0.97	2.56	3.331 (4)	136

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₉H₁₆Cl₄N₂O₂)]
M_r	509.68
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	12.4002 (10), 8.4570 (7), 20.0316 (19)
β (°)	97.278 (4)
V (Å³)	2083.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.58
Crystal size (mm)	0.25 × 0.18 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.694, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	18291, 4988, 2882
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.105, 1.00
No. of reflections	4988
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.36

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).