Dichlorido{2-[(4-iodo-phen-yl)imino-meth-yl]pyridine-κN,N'}copper(II).

The Cu(II) atom in the title complex, [CuCl(2)(C(12)H(9)IN(2))], has a square-planar coordination being N,N'-chelated by the Schiff base ligand, and by two Cl atoms. The geometry is distorted towards square pyramidal owing to a long Cu⋯Cl inter-action of 2.941 (1) Å. This results in the formation of a zigzag chain structure propagating in the c-axis direction.

Related literature

For background to the synthesis and structure of metal complexes of diimines, see: Yamada (1999 ▶). For the structure of the zinc chloride complex of the same ligand, see: Dehghanpour et al. (2007 ▶).

Experimental

Crystal data

[CuCl2(C12H9IN2)]

M = 442.55

Monoclinic,

a = 12.2721 (5) Å

b = 15.2159 (5) Å

c = 7.4709 (2) Å

β = 94.8913 (10)°

V = 1389.97 (8) Å3

Z = 4

Mo Kα radiation

μ = 4.16 mm−1

T = 295 K

0.31 × 0.25 × 0.17 mm

Data collection

Rigaku RAXIS-RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.359, T max = 0.538 (expected range = 0.329–0.493)

21713 measured reflections

3166 independent reflections

2650 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.079

S = 1.05

3166 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.88 e Å−3

Δρmin = −0.51 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, 9R. DOI: 10.1107/S1600536809011684/su2104sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011684/su2104Isup2.hkl

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

[CuCl2(C12H9IN2)]	F(000) = 844
Mr = 442.55	Dx = 2.115 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13838 reflections
a = 12.2721 (5) Å	θ = 3.1–27.5°
b = 15.2159 (5) Å	µ = 4.16 mm−1
c = 7.4709 (2) Å	T = 295 K
β = 94.8913 (10)°	Block, green
V = 1389.97 (8) Å3	0.31 × 0.25 × 0.17 mm
Z = 4

Rigaku RAXIS-RAPID diffractometer	3166 independent reflections
Radiation source: fine-focus sealed tube	2650 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 10.000 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −15→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→19
Tmin = 0.359, Tmax = 0.538	l = −9→9
21713 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.6865P] where P = (Fo2 + 2Fc2)/3
3166 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.88 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

	x	y	z	Uiso*/Ueq
I1	−0.001646 (16)	0.649922 (16)	0.55181 (3)	0.05798 (10)
Cu1	0.60873 (3)	0.72391 (2)	0.87653 (5)	0.03844 (11)
Cl1	0.72032 (6)	0.82416 (5)	1.01818 (12)	0.05137 (19)
Cl2	0.51519 (6)	0.82558 (5)	0.71178 (11)	0.04616 (18)
N1	0.70612 (18)	0.62040 (15)	0.9438 (3)	0.0375 (5)
N2	0.50252 (17)	0.62295 (15)	0.7935 (3)	0.0334 (4)
C1	0.8056 (2)	0.6212 (2)	1.0289 (4)	0.0469 (7)
H1	0.8344	0.6738	1.0752	0.056*
C2	0.8676 (2)	0.5448 (2)	1.0503 (5)	0.0520 (8)
H2	0.9368	0.5463	1.1114	0.062*
C3	0.8259 (3)	0.4672 (2)	0.9809 (5)	0.0489 (7)
H3	0.8677	0.4162	0.9895	0.059*
C4	0.7210 (3)	0.4657 (2)	0.8980 (4)	0.0443 (6)
H4	0.6902	0.4135	0.8530	0.053*
C5	0.6629 (2)	0.54354 (18)	0.8832 (4)	0.0365 (6)
C6	0.5499 (2)	0.54841 (18)	0.8064 (4)	0.0378 (6)
H6	0.5128	0.4977	0.7672	0.045*
C7	0.3893 (2)	0.62851 (18)	0.7297 (4)	0.0350 (5)
C8	0.3398 (2)	0.5679 (2)	0.6095 (4)	0.0446 (6)
H8	0.3814	0.5233	0.5643	0.054*
C9	0.2287 (2)	0.5736 (2)	0.5565 (4)	0.0479 (7)
H9	0.1957	0.5323	0.4775	0.057*
C10	0.1677 (2)	0.64099 (19)	0.6219 (4)	0.0417 (6)
C11	0.2166 (2)	0.70219 (19)	0.7420 (4)	0.0422 (6)
H11	0.1753	0.7475	0.7852	0.051*
C12	0.3266 (2)	0.69542 (18)	0.7964 (4)	0.0385 (6)
H12	0.3591	0.7357	0.8781	0.046*

	U11	U22	U33	U12	U13	U23
I1	0.02714 (12)	0.06908 (18)	0.07514 (18)	0.00149 (8)	−0.01061 (10)	0.00131 (11)
Cu1	0.02850 (18)	0.03088 (18)	0.0536 (2)	0.00103 (12)	−0.00989 (14)	−0.00045 (14)
Cl1	0.0377 (4)	0.0440 (4)	0.0702 (5)	−0.0064 (3)	−0.0082 (3)	−0.0106 (4)
Cl2	0.0382 (4)	0.0366 (3)	0.0624 (4)	0.0042 (3)	−0.0032 (3)	0.0115 (3)
N1	0.0270 (11)	0.0373 (11)	0.0472 (12)	0.0010 (9)	−0.0036 (9)	0.0017 (11)
N2	0.0265 (11)	0.0321 (10)	0.0404 (11)	0.0000 (8)	−0.0033 (8)	0.0008 (9)
C1	0.0306 (14)	0.0500 (16)	0.0578 (17)	0.0032 (12)	−0.0087 (12)	−0.0016 (15)
C2	0.0279 (14)	0.0624 (19)	0.0640 (19)	0.0063 (13)	−0.0055 (13)	0.0086 (16)
C3	0.0358 (16)	0.0470 (16)	0.0640 (18)	0.0124 (12)	0.0054 (13)	0.0129 (15)
C4	0.0390 (15)	0.0367 (14)	0.0570 (17)	0.0040 (11)	0.0022 (13)	0.0056 (13)
C5	0.0287 (13)	0.0353 (13)	0.0449 (14)	0.0019 (10)	−0.0002 (10)	0.0041 (12)
C6	0.0315 (13)	0.0325 (13)	0.0484 (15)	−0.0023 (10)	−0.0027 (11)	0.0010 (12)
C7	0.0264 (12)	0.0349 (12)	0.0429 (13)	0.0000 (10)	−0.0022 (10)	0.0020 (12)
C8	0.0304 (14)	0.0513 (17)	0.0513 (16)	0.0015 (12)	−0.0014 (11)	−0.0108 (14)
C9	0.0331 (15)	0.0581 (18)	0.0507 (16)	−0.0033 (13)	−0.0069 (12)	−0.0096 (15)
C10	0.0244 (13)	0.0492 (16)	0.0503 (16)	−0.0011 (11)	−0.0046 (11)	0.0049 (13)
C11	0.0320 (14)	0.0387 (14)	0.0556 (16)	0.0054 (11)	0.0017 (11)	0.0012 (13)
C12	0.0326 (14)	0.0360 (13)	0.0457 (14)	−0.0010 (11)	−0.0036 (11)	−0.0015 (12)

I1—C10	2.104 (3)	C4—C5	1.383 (4)
Cu1—N1	2.015 (2)	C4—H4	0.9300
Cu1—N2	2.075 (2)	C5—C6	1.457 (4)
Cu1—Cl1	2.253 (1)	C6—H6	0.9300
Cu1—Cl2	2.233 (1)	C7—C8	1.390 (4)
N1—C1	1.328 (4)	C7—C12	1.393 (4)
N1—C5	1.346 (4)	C8—C9	1.389 (4)
N2—C6	1.274 (4)	C8—H8	0.9300
N2—C7	1.433 (3)	C9—C10	1.384 (4)
C1—C2	1.391 (4)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.393 (4)
C2—C3	1.371 (5)	C11—C12	1.380 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.380 (4)	C12—H12	0.9300
C3—H3	0.9300
N1—Cu1—N2	80.79 (9)	N1—C5—C4	122.1 (3)
N1—Cu1—Cl2	160.96 (7)	N1—C5—C6	115.0 (2)
N1—Cu1—Cl1	95.07 (7)	C4—C5—C6	122.8 (3)
N2—Cu1—Cl1	169.40 (7)	N2—C6—C5	119.2 (2)
N2—Cu1—Cl2	93.89 (6)	N2—C6—H6	120.4
Cl1—Cu2—Cl1	93.05 (3)	C5—C6—H6	120.4
C1—N1—C5	119.3 (2)	C8—C7—C12	119.5 (2)
C1—N1—Cu1	127.9 (2)	C8—C7—N2	122.2 (2)
C5—N1—Cu1	112.76 (17)	C12—C7—N2	118.3 (2)
C6—N2—C7	120.1 (2)	C7—C8—C9	120.5 (3)
C6—N2—Cu1	111.44 (18)	C7—C8—H8	119.8
C7—N2—Cu1	128.50 (17)	C9—C8—H8	119.8
N1—C1—C2	121.2 (3)	C10—C9—C8	119.5 (3)
N1—C1—H1	119.4	C10—C9—H9	120.3
C2—C1—H1	119.4	C8—C9—H9	120.3
C3—C2—C1	119.6 (3)	C9—C10—C11	120.4 (3)
C3—C2—H2	120.2	C9—C10—I1	120.9 (2)
C1—C2—H2	120.2	C11—C10—I1	118.7 (2)
C2—C3—C4	119.2 (3)	C12—C11—C10	119.8 (3)
C2—C3—H3	120.4	C12—C11—H11	120.1
C4—C3—H3	120.4	C10—C11—H11	120.1
C3—C4—C5	118.5 (3)	C11—C12—C7	120.3 (3)
C3—C4—H4	120.8	C11—C12—H12	119.8
C5—C4—H4	120.8	C7—C12—H12	119.8
N2—Cu1—N1—C1	−175.5 (3)	C3—C4—C5—N1	1.4 (5)
Cl2—Cu1—N1—C1	109.5 (3)	C3—C4—C5—C6	−176.8 (3)
Cl1—Cu1—N1—C1	−5.4 (3)	C7—N2—C6—C5	−175.7 (2)
N2—Cu1—N1—C5	8.14 (19)	Cu1—N2—C6—C5	3.6 (3)
Cl2—Cu1—N1—C5	−66.8 (3)	N1—C5—C6—N2	3.3 (4)
Cl1—Cu1—N1—C5	178.30 (18)	C4—C5—C6—N2	−178.3 (3)
N1—Cu1—N2—C6	−6.3 (2)	C6—N2—C7—C8	−29.4 (4)
Cl2—Cu1—N2—C6	155.25 (19)	Cu1—N2—C7—C8	151.3 (2)
Cl1—Cu1—N2—C6	−74.0 (4)	C6—N2—C7—C12	148.2 (3)
N1—Cu1—N2—C7	172.9 (2)	Cu1—N2—C7—C12	−31.0 (3)
Cl2—Cu1—N2—C7	−25.5 (2)	C12—C7—C8—C9	−0.2 (4)
Cl1—Cu1—N2—C7	105.3 (4)	N2—C7—C8—C9	177.4 (3)
C5—N1—C1—C2	2.6 (5)	C7—C8—C9—C10	1.1 (5)
Cu1—N1—C1—C2	−173.5 (2)	C8—C9—C10—C11	−0.8 (5)
N1—C1—C2—C3	0.6 (5)	C8—C9—C10—I1	−178.1 (2)
C1—C2—C3—C4	−2.9 (5)	C9—C10—C11—C12	−0.2 (5)
C2—C3—C4—C5	1.9 (5)	I1—C10—C11—C12	177.1 (2)
C1—N1—C5—C4	−3.7 (4)	C10—C11—C12—C7	1.0 (4)
Cu1—N1—C5—C4	173.0 (2)	C8—C7—C12—C11	−0.8 (4)
C1—N1—C5—C6	174.7 (3)	N2—C7—C12—C11	−178.6 (3)
Cu1—N1—C5—C6	−8.6 (3)