catena-Poly[copper(II)-{μ(3)-4,4'-dichloro-2,2'-[butane-1,4-diylbis(nitrilo-methanyl-yl-idene)]diphenolato-κN,O:N',O':O'}].

The asymmetric unit of the title coordination polymer, [Cu(C(18)H(16)Cl(2)N(2)O(2))](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 bis-ects 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, inter-molecular π-π inter-actions [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 = 426.77

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.03

7465 reflections

226 parameters

H-atom parameters constrained

Δρmax = 1.07 e Å−3

Δρmin = −0.70 e Å−3

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 ▶).

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

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

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

[Cu(C18H16Cl2N2O2)]	F(000) = 1736
Mr = 426.77	Dx = 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

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

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(Fo2) + (0.0534P)2 + 2.3966P] where P = (Fo2 + 2Fc2)/3
7465 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 1.07 e Å−3
0 restraints	Δρmin = −0.69 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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