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

In the title Schiff base complex, [Cu(C(19)H(18)Cl(2)N(2)O(2))], the Cu(II) ion is coordinated in a distorted square-planar environment by two N atoms and two O atoms of the tetra-dentate ligand. The dihedral angle between the benzene rings is 36.86 (14)°. In the crystal, mol-ecules are linked into inversion dimers by pairs of weak C-H⋯O hydrogen bonds. In addition, π-π [centroid-centroid distance = 3.7279 (16) Å] and weak C-H⋯π inter-actions are observed.

Related literature

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

Experimental

Crystal data

[Cu(C19H18Cl2N2O2)]

M = 440.79

Triclinic,

a = 9.4213 (12) Å

b = 9.5718 (13) Å

c = 11.4392 (15) Å

α = 74.478 (10)°

β = 78.635 (10)°

γ = 73.339 (10)°

V = 944.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.46 mm−1

T = 296 K

0.23 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.731, T max = 0.893

8620 measured reflections

4302 independent reflections

3369 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.098

S = 1.00

4302 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.46 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/S1600536812033491/lh5504sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033491/lh5504Isup2.hkl

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

[Cu(C19H18Cl2N2O2)]	Z = 2
Mr = 440.79	F(000) = 450
Triclinic, P1	Dx = 1.551 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4213 (12) Å	Cell parameters from 1540 reflections
b = 9.5718 (13) Å	θ = 2.5–27.4°
c = 11.4392 (15) Å	µ = 1.46 mm−1
α = 74.478 (10)°	T = 296 K
β = 78.635 (10)°	Block, dark-green
γ = 73.339 (10)°	0.23 × 0.12 × 0.08 mm
V = 944.1 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4302 independent reflections
Radiation source: fine-focus sealed tube	3369 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.731, Tmax = 0.893	k = −12→12
8620 measured reflections	l = −14→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0521P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
4302 reflections	Δρmax = 0.44 e Å−3
236 parameters	Δρmin = −0.46 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (2)

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
Cu1	0.59520 (4)	0.06692 (3)	0.63656 (3)	0.03281 (12)
Cl1	0.14886 (11)	−0.15287 (10)	1.21334 (8)	0.0638 (2)
Cl2	0.81316 (14)	0.43389 (11)	0.01358 (8)	0.0801 (3)
O1	0.4216 (2)	0.1436 (2)	0.74001 (17)	0.0395 (4)
O2	0.5916 (2)	0.2592 (2)	0.53387 (17)	0.0402 (4)
N1	0.6589 (2)	−0.1147 (2)	0.7608 (2)	0.0345 (5)
N2	0.6982 (2)	−0.0370 (2)	0.50664 (19)	0.0323 (5)
C1	0.3645 (3)	0.0694 (3)	0.8440 (2)	0.0336 (5)
C2	0.2211 (3)	0.1361 (3)	0.8969 (3)	0.0392 (6)
H2A	0.1697	0.2291	0.8560	0.047*
C3	0.1548 (3)	0.0676 (3)	1.0075 (3)	0.0439 (7)
H3A	0.0600	0.1141	1.0401	0.053*
C4	0.2299 (3)	−0.0707 (3)	1.0697 (3)	0.0427 (7)
C5	0.3678 (3)	−0.1413 (3)	1.0215 (2)	0.0401 (6)
H5A	0.4166	−0.2344	1.0641	0.048*
C6	0.4369 (3)	−0.0746 (3)	0.9079 (2)	0.0341 (5)
C7	0.5839 (3)	−0.1549 (3)	0.8646 (2)	0.0367 (6)
H7A	0.6278	−0.2433	0.9163	0.044*
C8	0.8107 (3)	−0.2035 (3)	0.7313 (3)	0.0391 (6)
H8A	0.8418	−0.2764	0.8046	0.047*
H8B	0.8782	−0.1380	0.7059	0.047*
C9	0.8246 (3)	−0.2868 (3)	0.6290 (3)	0.0370 (6)
C10	0.7130 (3)	−0.1996 (3)	0.5388 (2)	0.0365 (6)
H10A	0.7437	−0.2370	0.4645	0.044*
H10B	0.6158	−0.2182	0.5739	0.044*
C11	0.7392 (3)	0.0260 (3)	0.3960 (2)	0.0326 (5)
H11A	0.7864	−0.0363	0.3424	0.039*
C12	0.7187 (3)	0.1840 (3)	0.3477 (2)	0.0319 (5)
C13	0.7706 (3)	0.2307 (3)	0.2225 (2)	0.0388 (6)
H13A	0.8194	0.1597	0.1766	0.047*
C14	0.7498 (3)	0.3784 (3)	0.1688 (3)	0.0441 (7)
C15	0.6757 (3)	0.4870 (3)	0.2359 (3)	0.0450 (7)
H15A	0.6615	0.5880	0.1981	0.054*
C16	0.6242 (3)	0.4443 (3)	0.3570 (3)	0.0406 (6)
H16A	0.5745	0.5175	0.4005	0.049*
C17	0.6445 (3)	0.2919 (3)	0.4180 (2)	0.0333 (5)
C18	0.7882 (4)	−0.4381 (3)	0.6845 (3)	0.0563 (8)
H18A	0.7969	−0.4890	0.6206	0.084*
H18B	0.6880	−0.4233	0.7263	0.084*
H18C	0.8568	−0.4973	0.7414	0.084*
C19	0.9840 (4)	−0.3059 (4)	0.5632 (4)	0.0598 (9)
H19A	0.9953	−0.3568	0.4989	0.090*
H19B	1.0529	−0.3636	0.6203	0.090*
H19C	1.0042	−0.2093	0.5290	0.090*

	U11	U22	U33	U12	U13	U23
Cu1	0.03676 (19)	0.02733 (17)	0.02913 (18)	−0.00348 (12)	0.00110 (12)	−0.00637 (12)
Cl1	0.0809 (6)	0.0601 (5)	0.0447 (4)	−0.0320 (5)	0.0197 (4)	−0.0069 (4)
Cl2	0.1256 (9)	0.0540 (5)	0.0398 (4)	−0.0221 (6)	0.0211 (5)	0.0012 (4)
O1	0.0420 (10)	0.0334 (9)	0.0324 (9)	−0.0021 (8)	0.0039 (8)	−0.0038 (8)
O2	0.0512 (11)	0.0292 (9)	0.0333 (10)	−0.0068 (8)	0.0072 (8)	−0.0083 (8)
N1	0.0364 (11)	0.0319 (11)	0.0326 (11)	−0.0007 (9)	−0.0056 (9)	−0.0103 (9)
N2	0.0372 (11)	0.0254 (10)	0.0335 (11)	−0.0062 (9)	−0.0034 (9)	−0.0074 (9)
C1	0.0388 (13)	0.0343 (13)	0.0295 (12)	−0.0111 (11)	−0.0020 (11)	−0.0099 (11)
C2	0.0383 (14)	0.0366 (14)	0.0392 (14)	−0.0071 (12)	0.0007 (12)	−0.0092 (12)
C3	0.0404 (15)	0.0474 (16)	0.0446 (16)	−0.0147 (13)	0.0069 (13)	−0.0165 (14)
C4	0.0553 (17)	0.0431 (15)	0.0338 (14)	−0.0247 (14)	0.0059 (13)	−0.0103 (12)
C5	0.0530 (16)	0.0358 (14)	0.0337 (14)	−0.0167 (13)	−0.0044 (12)	−0.0064 (11)
C6	0.0408 (14)	0.0342 (13)	0.0294 (12)	−0.0124 (11)	−0.0030 (11)	−0.0083 (11)
C7	0.0449 (15)	0.0296 (12)	0.0344 (13)	−0.0042 (11)	−0.0110 (12)	−0.0065 (11)
C8	0.0360 (14)	0.0376 (14)	0.0424 (15)	−0.0007 (11)	−0.0089 (12)	−0.0128 (12)
C9	0.0375 (14)	0.0280 (12)	0.0416 (15)	−0.0014 (11)	−0.0019 (12)	−0.0106 (11)
C10	0.0464 (15)	0.0259 (12)	0.0383 (14)	−0.0102 (11)	−0.0068 (12)	−0.0071 (11)
C11	0.0346 (13)	0.0327 (12)	0.0311 (13)	−0.0070 (10)	−0.0021 (10)	−0.0114 (11)
C12	0.0323 (12)	0.0306 (12)	0.0312 (13)	−0.0085 (10)	−0.0004 (10)	−0.0065 (10)
C13	0.0440 (15)	0.0368 (14)	0.0328 (13)	−0.0098 (12)	0.0044 (12)	−0.0101 (11)
C14	0.0536 (17)	0.0414 (15)	0.0319 (14)	−0.0149 (13)	0.0013 (13)	−0.0009 (12)
C15	0.0501 (16)	0.0305 (13)	0.0462 (16)	−0.0087 (12)	−0.0009 (13)	−0.0002 (12)
C16	0.0419 (14)	0.0291 (13)	0.0425 (15)	−0.0037 (11)	0.0059 (12)	−0.0084 (11)
C17	0.0304 (12)	0.0327 (12)	0.0336 (13)	−0.0066 (10)	0.0005 (10)	−0.0067 (11)
C18	0.081 (2)	0.0308 (14)	0.0511 (18)	−0.0071 (15)	−0.0115 (17)	−0.0047 (13)
C19	0.0419 (17)	0.066 (2)	0.068 (2)	−0.0013 (16)	0.0039 (16)	−0.0295 (19)

Cu1—O2	1.8952 (18)	C8—H8A	0.9700
Cu1—O1	1.9050 (18)	C8—H8B	0.9700
Cu1—N2	1.952 (2)	C9—C18	1.525 (4)
Cu1—N1	1.953 (2)	C9—C19	1.525 (4)
Cl1—C4	1.749 (3)	C9—C10	1.527 (4)
Cl2—C14	1.747 (3)	C10—H10A	0.9700
O1—C1	1.312 (3)	C10—H10B	0.9700
O2—C17	1.308 (3)	C11—C12	1.434 (3)
N1—C7	1.280 (3)	C11—H11A	0.9300
N1—C8	1.466 (3)	C12—C13	1.413 (4)
N2—C11	1.283 (3)	C12—C17	1.418 (4)
N2—C10	1.471 (3)	C13—C14	1.355 (4)
C1—C2	1.411 (4)	C13—H13A	0.9300
C1—C6	1.421 (4)	C14—C15	1.398 (4)
C2—C3	1.378 (4)	C15—C16	1.367 (4)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.385 (4)	C16—C17	1.414 (4)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.365 (4)	C18—H18A	0.9600
C5—C6	1.407 (4)	C18—H18B	0.9600
C5—H5A	0.9300	C18—H18C	0.9600
C6—C7	1.442 (4)	C19—H19A	0.9600
C7—H7A	0.9300	C19—H19B	0.9600
C8—C9	1.550 (4)	C19—H19C	0.9600
O2—Cu1—O1	92.08 (8)	C19—C9—C10	110.3 (3)
O2—Cu1—N2	93.57 (8)	C18—C9—C8	109.9 (2)
O1—Cu1—N2	152.81 (9)	C19—C9—C8	107.9 (2)
O2—Cu1—N1	159.03 (9)	C10—C9—C8	111.1 (2)
O1—Cu1—N1	93.46 (9)	N2—C10—C9	114.0 (2)
N2—Cu1—N1	90.69 (9)	N2—C10—H10A	108.7
C1—O1—Cu1	126.44 (16)	C9—C10—H10A	108.7
C17—O2—Cu1	127.77 (16)	N2—C10—H10B	108.7
C7—N1—C8	119.4 (2)	C9—C10—H10B	108.7
C7—N1—Cu1	125.79 (18)	H10A—C10—H10B	107.6
C8—N1—Cu1	114.63 (18)	N2—C11—C12	125.8 (2)
C11—N2—C10	119.1 (2)	N2—C11—H11A	117.1
C11—N2—Cu1	125.51 (17)	C12—C11—H11A	117.1
C10—N2—Cu1	115.01 (17)	C13—C12—C17	120.0 (2)
O1—C1—C2	118.3 (2)	C13—C12—C11	116.9 (2)
O1—C1—C6	124.7 (2)	C17—C12—C11	123.1 (2)
C2—C1—C6	117.0 (2)	C14—C13—C12	120.4 (2)
C3—C2—C1	122.0 (3)	C14—C13—H13A	119.8
C3—C2—H2A	119.0	C12—C13—H13A	119.8
C1—C2—H2A	119.0	C13—C14—C15	120.7 (3)
C2—C3—C4	119.7 (3)	C13—C14—Cl2	119.7 (2)
C2—C3—H3A	120.1	C15—C14—Cl2	119.6 (2)
C4—C3—H3A	120.1	C16—C15—C14	119.9 (3)
C5—C4—C3	120.6 (3)	C16—C15—H15A	120.1
C5—C4—Cl1	119.9 (2)	C14—C15—H15A	120.1
C3—C4—Cl1	119.5 (2)	C15—C16—C17	121.8 (2)
C4—C5—C6	120.7 (3)	C15—C16—H16A	119.1
C4—C5—H5A	119.6	C17—C16—H16A	119.1
C6—C5—H5A	119.6	O2—C17—C16	118.5 (2)
C5—C6—C1	119.9 (2)	O2—C17—C12	124.3 (2)
C5—C6—C7	117.3 (2)	C16—C17—C12	117.2 (2)
C1—C6—C7	122.8 (2)	C9—C18—H18A	109.5
N1—C7—C6	125.4 (2)	C9—C18—H18B	109.5
N1—C7—H7A	117.3	H18A—C18—H18B	109.5
C6—C7—H7A	117.3	C9—C18—H18C	109.5
N1—C8—C9	113.3 (2)	H18A—C18—H18C	109.5
N1—C8—H8A	108.9	H18B—C18—H18C	109.5
C9—C8—H8A	108.9	C9—C19—H19A	109.5
N1—C8—H8B	108.9	C9—C19—H19B	109.5
C9—C8—H8B	108.9	H19A—C19—H19B	109.5
H8A—C8—H8B	107.7	C9—C19—H19C	109.5
C18—C9—C19	111.0 (3)	H19A—C19—H19C	109.5
C18—C9—C10	106.7 (2)	H19B—C19—H19C	109.5
O2—Cu1—O1—C1	−172.8 (2)	C8—N1—C7—C6	176.8 (2)
N2—Cu1—O1—C1	85.3 (3)	Cu1—N1—C7—C6	1.2 (4)
N1—Cu1—O1—C1	−13.0 (2)	C5—C6—C7—N1	176.0 (2)
O1—Cu1—O2—C17	−153.3 (2)	C1—C6—C7—N1	−7.1 (4)
N2—Cu1—O2—C17	0.1 (2)	C7—N1—C8—C9	111.5 (3)
N1—Cu1—O2—C17	101.4 (3)	Cu1—N1—C8—C9	−72.4 (3)
O2—Cu1—N1—C7	112.0 (3)	N1—C8—C9—C18	−87.2 (3)
O1—Cu1—N1—C7	6.9 (2)	N1—C8—C9—C19	151.7 (3)
N2—Cu1—N1—C7	−146.2 (2)	N1—C8—C9—C10	30.7 (3)
O2—Cu1—N1—C8	−63.9 (3)	C11—N2—C10—C9	114.9 (3)
O1—Cu1—N1—C8	−168.88 (17)	Cu1—N2—C10—C9	−71.5 (3)
N2—Cu1—N1—C8	38.01 (18)	C18—C9—C10—N2	161.2 (2)
O2—Cu1—N2—C11	0.1 (2)	C19—C9—C10—N2	−78.2 (3)
O1—Cu1—N2—C11	101.7 (3)	C8—C9—C10—N2	41.4 (3)
N1—Cu1—N2—C11	−159.3 (2)	C10—N2—C11—C12	173.6 (2)
O2—Cu1—N2—C10	−172.92 (17)	Cu1—N2—C11—C12	0.8 (4)
O1—Cu1—N2—C10	−71.3 (3)	N2—C11—C12—C13	−179.3 (3)
N1—Cu1—N2—C10	27.62 (18)	N2—C11—C12—C17	−2.0 (4)
Cu1—O1—C1—C2	−168.66 (18)	C17—C12—C13—C14	−0.1 (4)
Cu1—O1—C1—C6	11.3 (4)	C11—C12—C13—C14	177.2 (3)
O1—C1—C2—C3	−178.2 (2)	C12—C13—C14—C15	−0.5 (5)
C6—C1—C2—C3	1.8 (4)	C12—C13—C14—Cl2	−179.4 (2)
C1—C2—C3—C4	0.2 (4)	C13—C14—C15—C16	0.3 (5)
C2—C3—C4—C5	−1.3 (4)	Cl2—C14—C15—C16	179.2 (2)
C2—C3—C4—Cl1	177.0 (2)	C14—C15—C16—C17	0.5 (5)
C3—C4—C5—C6	0.4 (4)	Cu1—O2—C17—C16	177.33 (19)
Cl1—C4—C5—C6	−177.9 (2)	Cu1—O2—C17—C12	−1.2 (4)
C4—C5—C6—C1	1.7 (4)	C15—C16—C17—O2	−179.7 (3)
C4—C5—C6—C7	178.7 (2)	C15—C16—C17—C12	−1.0 (4)
O1—C1—C6—C5	177.4 (2)	C13—C12—C17—O2	179.4 (2)
C2—C1—C6—C5	−2.7 (4)	C11—C12—C17—O2	2.2 (4)
O1—C1—C6—C7	0.5 (4)	C13—C12—C17—C16	0.8 (4)
C2—C1—C6—C7	−179.6 (2)	C11—C12—C17—C16	−176.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2i	0.93	2.46	3.367 (3)	165
C10—H10B···Cgii	0.97	2.65	3.452 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg is centroid of Cu1/O2/C17/C12/C11/N2.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2i	0.93	2.46	3.367 (3)	165
C10—H10B⋯Cg ii	0.97	2.65	3.452 (3)	140

Symmetry codes: (i) ; (ii) .