{4,4',6,6'-Tetra-chloro-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methanylyl-idene)]}copper(II).

In the title Schiff base complex, [Cu(C(19)H(16)Cl(4)N(2)O(2))], the geometry around the Cu(II) atom is distorted square-planar defined by the N(2)O(2) donor atoms of the coordinated ligand. The dihedral angle between the substituted benzene rings is 29.95 (16)°. In the crystal, mol-ecules are linked along the b axis, forming individual dimers through C-H⋯O inter-actions. The crystal structure is further stabilized by inter-molecular π-π inter-actions [centroid-centroid distance = 3.6131 (17) Å].

Related literature

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

Crystal data

[Cu(C19H16Cl4N2O2)]

M = 509.68

Monoclinic,

a = 12.4002 (10) Å

b = 8.4570 (7) Å

c = 20.0316 (19) Å

β = 97.278 (4)°

V = 2083.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.58 mm−1

T = 291 K

0.25 × 0.18 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.694, T max = 0.871

18291 measured reflections

4988 independent reflections

2882 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.105

S = 1.00

4988 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.36 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200195X/hp2025sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200195X/hp2025Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C19H16Cl4N2O2)]	F(000) = 1028
Mr = 509.68	Dx = 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

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

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(Fo2) + (0.0376P)2] where P = (Fo2 + 2Fc2)/3
4988 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) .