Diiodido[4'-(4-pyrid-yl)-2,2':6',2''-terpyridine-κN,N',N'']copper(II).

The Cu(II) atom in the title compound, [CuI(2)(C(20)H(14)N(4))], has a distorted square-pyramidal coordination formed by the N atoms of the tridentate 4'-(4-pyrid-yl)-2,2':6'2''-terpyridine (pyterpy) ligand and two I atoms; one of the I atoms is in the apical position. In contrast to other known square-pyramidal diiodido- and dibromidocopper complexes of the pyterpy ligand in which metal-halogen distances are significantly different, in the title compound the apical and equatorial Cu-I bonds are almost identical [2.6141 (8) and 2.6025 (8) Å, respectively].

Related literature

For related structures, see: Feng et al. (2006 ▶); Hou et al. (2004 ▶, 2005 ▶); Kutoglu et al. (1991 ▶); Shi et al. (2007 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

[CuI2(C20H14N4)]

M = 627.69

Monoclinic,

a = 11.9882 (8) Å

b = 14.642 (1) Å

c = 12.0291 (8) Å

β = 110.240 (1)°

V = 1981.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 4.23 mm−1

T = 294 K

0.25 × 0.23 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.361, T max = 0.467

11694 measured reflections

3894 independent reflections

3670 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.091

S = 1.30

3894 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.97 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020635/ya2124sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020635/ya2124Isup2.hkl

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

[CuI2(C20H14N4)]	F(000) = 1188
Mr = 627.69	Dx = 2.105 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1523 reflections
a = 11.9882 (8) Å	θ = 1.9–20.3°
b = 14.642 (1) Å	µ = 4.23 mm−1
c = 12.0291 (8) Å	T = 294 K
β = 110.240 (1)°	Block, black
V = 1981.1 (2) Å3	0.25 × 0.23 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	3894 independent reflections
Radiation source: fine-focus sealed tube	3670 reflections with I > 2σ(I)
graphite	Rint = 0.028
phi and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.361, Tmax = 0.467	k = −18→17
11694 measured reflections	l = −8→14

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.30	w = 1/[σ2(Fo2) + (0.0189P)2 + 6.8023P] where P = (Fo2 + 2Fc2)/3
3894 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.97 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 > 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	0.73294 (6)	0.14757 (4)	0.92788 (6)	0.02734 (17)
C1	1.1049 (6)	−0.1207 (5)	0.5460 (6)	0.0409 (15)
H1	1.0765	−0.1717	0.4986	0.049*
C2	1.0403 (5)	−0.0897 (4)	0.6143 (5)	0.0346 (14)
H2	0.9724	−0.1206	0.6142	0.042*
C3	1.0786 (5)	−0.0118 (4)	0.6828 (5)	0.0288 (12)
C4	1.1830 (5)	0.0295 (4)	0.6800 (5)	0.0343 (13)
H4	1.2126	0.0818	0.7241	0.041*
C5	1.2409 (6)	−0.0091 (4)	0.6106 (6)	0.0411 (16)
H5	1.3108	0.0187	0.6108	0.049*
C6	1.0106 (5)	0.0250 (4)	0.7539 (5)	0.0278 (12)
C7	0.9499 (5)	−0.0329 (4)	0.8056 (5)	0.0304 (13)
H7	0.9566	−0.0959	0.8006	0.036*
C8	0.8799 (5)	0.0042 (4)	0.8644 (5)	0.0253 (11)
C9	0.8078 (5)	−0.0505 (4)	0.9195 (5)	0.0279 (12)
C10	0.8152 (5)	−0.1438 (4)	0.9284 (5)	0.0347 (13)
H10	0.8651	−0.1760	0.8981	0.042*
C11	0.7474 (6)	−0.1892 (4)	0.9830 (6)	0.0421 (16)
H11	0.7519	−0.2523	0.9916	0.050*
C12	0.6724 (6)	−0.1390 (4)	1.0249 (6)	0.0442 (16)
H12	0.6249	−0.1677	1.0612	0.053*
C13	0.6698 (6)	−0.0452 (4)	1.0115 (6)	0.0404 (15)
H13	0.6197	−0.0115	1.0400	0.048*
C14	0.8092 (6)	0.3530 (4)	0.9194 (6)	0.0383 (14)
H14	0.7541	0.3645	0.9563	0.046*
C15	0.8637 (6)	0.4263 (4)	0.8878 (6)	0.0391 (15)
H15	0.8446	0.4858	0.9016	0.047*
C16	0.9473 (6)	0.4096 (4)	0.8354 (6)	0.0417 (16)
H16	0.9863	0.4577	0.8140	0.050*
C17	0.9724 (6)	0.3199 (4)	0.8149 (6)	0.0384 (15)
H17	1.0288	0.3069	0.7801	0.046*
C18	0.9120 (5)	0.2504 (4)	0.8473 (5)	0.0271 (12)
C19	0.9295 (5)	0.1515 (4)	0.8282 (5)	0.0259 (12)
C20	1.0022 (5)	0.1191 (4)	0.7688 (5)	0.0298 (12)
H20	1.0448	0.1595	0.7392	0.036*
I1	0.69282 (4)	0.20067 (3)	1.11708 (4)	0.04474 (14)
I2	0.54357 (4)	0.16793 (3)	0.73907 (4)	0.04683 (14)
N1	1.2047 (5)	−0.0826 (4)	0.5436 (5)	0.0455 (14)
N2	0.7357 (4)	−0.0010 (3)	0.9595 (4)	0.0310 (11)
N3	0.8694 (4)	0.0951 (3)	0.8736 (4)	0.0267 (10)
N4	0.8313 (4)	0.2670 (3)	0.8997 (4)	0.0298 (11)

	U11	U22	U33	U12	U13	U23
Cu1	0.0286 (4)	0.0248 (3)	0.0331 (4)	0.0006 (3)	0.0162 (3)	−0.0012 (3)
C1	0.046 (4)	0.039 (4)	0.040 (4)	0.006 (3)	0.018 (3)	−0.001 (3)
C2	0.037 (3)	0.030 (3)	0.041 (4)	0.003 (2)	0.019 (3)	−0.003 (3)
C3	0.031 (3)	0.026 (3)	0.031 (3)	0.007 (2)	0.012 (3)	0.005 (2)
C4	0.036 (3)	0.031 (3)	0.034 (3)	0.002 (3)	0.011 (3)	0.007 (3)
C5	0.038 (3)	0.043 (4)	0.052 (4)	0.010 (3)	0.027 (3)	0.013 (3)
C6	0.027 (3)	0.029 (3)	0.029 (3)	0.001 (2)	0.011 (2)	0.001 (2)
C7	0.038 (3)	0.020 (3)	0.032 (3)	0.003 (2)	0.011 (3)	−0.001 (2)
C8	0.026 (3)	0.023 (3)	0.025 (3)	−0.001 (2)	0.006 (2)	0.003 (2)
C9	0.025 (3)	0.027 (3)	0.029 (3)	−0.003 (2)	0.005 (2)	−0.002 (2)
C10	0.036 (3)	0.032 (3)	0.038 (3)	−0.002 (2)	0.016 (3)	0.002 (3)
C11	0.050 (4)	0.026 (3)	0.054 (4)	−0.011 (3)	0.022 (3)	0.006 (3)
C12	0.045 (4)	0.044 (4)	0.054 (4)	−0.014 (3)	0.030 (3)	0.003 (3)
C13	0.038 (3)	0.040 (4)	0.048 (4)	−0.004 (3)	0.022 (3)	−0.003 (3)
C14	0.043 (4)	0.032 (3)	0.044 (4)	0.005 (3)	0.019 (3)	−0.003 (3)
C15	0.043 (4)	0.023 (3)	0.049 (4)	−0.001 (3)	0.014 (3)	−0.001 (3)
C16	0.043 (4)	0.024 (3)	0.060 (4)	−0.007 (3)	0.019 (3)	0.006 (3)
C17	0.041 (4)	0.029 (3)	0.051 (4)	0.000 (3)	0.023 (3)	0.002 (3)
C18	0.024 (3)	0.025 (3)	0.031 (3)	0.001 (2)	0.008 (2)	0.004 (2)
C19	0.030 (3)	0.023 (3)	0.028 (3)	−0.002 (2)	0.014 (2)	0.003 (2)
C20	0.035 (3)	0.025 (3)	0.031 (3)	−0.005 (2)	0.014 (3)	0.003 (2)
I1	0.0565 (3)	0.0431 (3)	0.0441 (3)	0.0026 (2)	0.0296 (2)	−0.0038 (2)
I2	0.0424 (3)	0.0349 (2)	0.0504 (3)	−0.00135 (18)	−0.0003 (2)	0.0007 (2)
N1	0.054 (4)	0.041 (3)	0.052 (4)	0.013 (3)	0.032 (3)	0.001 (3)
N2	0.033 (3)	0.027 (2)	0.038 (3)	0.001 (2)	0.019 (2)	0.000 (2)
N3	0.029 (2)	0.025 (2)	0.027 (2)	0.0012 (19)	0.010 (2)	0.0025 (19)
N4	0.028 (2)	0.027 (2)	0.036 (3)	−0.0025 (19)	0.013 (2)	0.000 (2)

Cu1—N3	2.104 (4)	C9—C10	1.370 (8)
Cu1—N4	2.199 (5)	C10—C11	1.380 (8)
Cu1—N2	2.206 (5)	C10—H10	0.9300
Cu1—I1	2.6025 (8)	C11—C12	1.383 (9)
Cu1—I2	2.6141 (8)	C11—H11	0.9300
C1—N1	1.330 (8)	C12—C13	1.381 (9)
C1—C2	1.386 (8)	C12—H12	0.9300
C1—H1	0.9300	C13—N2	1.333 (7)
C2—C3	1.389 (8)	C13—H13	0.9300
C2—H2	0.9300	C14—N4	1.325 (7)
C3—C4	1.401 (8)	C14—C15	1.376 (9)
C3—C6	1.473 (7)	C14—H14	0.9300
C4—C5	1.379 (8)	C15—C16	1.378 (9)
C4—H4	0.9300	C15—H15	0.9300
C5—N1	1.324 (9)	C16—C17	1.388 (8)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.396 (8)	C17—C18	1.381 (8)
C6—C20	1.397 (8)	C17—H17	0.9300
C7—C8	1.382 (8)	C18—N4	1.347 (7)
C7—H7	0.9300	C18—C19	1.493 (7)
C8—N3	1.345 (7)	C19—N3	1.331 (6)
C8—C9	1.492 (7)	C19—C20	1.387 (8)
C9—N2	1.340 (7)	C20—H20	0.9300
N3—Cu1—N4	74.14 (17)	C10—C11—C12	118.8 (6)
N3—Cu1—N2	74.17 (17)	C10—C11—H11	120.6
N4—Cu1—N2	146.45 (17)	C12—C11—H11	120.6
N3—Cu1—I1	141.15 (13)	C13—C12—C11	118.5 (6)
N4—Cu1—I1	99.68 (13)	C13—C12—H12	120.7
N2—Cu1—I1	98.03 (13)	C11—C12—H12	120.7
N3—Cu1—I2	107.86 (13)	N2—C13—C12	123.0 (6)
N4—Cu1—I2	97.26 (13)	N2—C13—H13	118.5
N2—Cu1—I2	102.65 (13)	C12—C13—H13	118.5
I1—Cu1—I2	110.98 (3)	N4—C14—C15	123.3 (6)
N1—C1—C2	124.5 (6)	N4—C14—H14	118.4
N1—C1—H1	117.7	C15—C14—H14	118.4
C2—C1—H1	117.7	C14—C15—C16	118.5 (6)
C1—C2—C3	118.9 (6)	C14—C15—H15	120.7
C1—C2—H2	120.6	C16—C15—H15	120.7
C3—C2—H2	120.6	C15—C16—C17	119.1 (6)
C2—C3—C4	117.0 (5)	C15—C16—H16	120.5
C2—C3—C6	120.7 (5)	C17—C16—H16	120.5
C4—C3—C6	122.3 (5)	C18—C17—C16	118.7 (6)
C5—C4—C3	118.7 (6)	C18—C17—H17	120.7
C5—C4—H4	120.7	C16—C17—H17	120.7
C3—C4—H4	120.7	N4—C18—C17	122.1 (5)
N1—C5—C4	125.0 (6)	N4—C18—C19	114.1 (5)
N1—C5—H5	117.5	C17—C18—C19	123.8 (5)
C4—C5—H5	117.5	N3—C19—C20	121.7 (5)
C7—C6—C20	118.0 (5)	N3—C19—C18	114.4 (5)
C7—C6—C3	121.0 (5)	C20—C19—C18	123.9 (5)
C20—C6—C3	121.0 (5)	C19—C20—C6	119.3 (5)
C8—C7—C6	119.4 (5)	C19—C20—H20	120.4
C8—C7—H7	120.3	C6—C20—H20	120.4
C6—C7—H7	120.3	C5—N1—C1	115.9 (5)
N3—C8—C7	121.5 (5)	C13—N2—C9	117.8 (5)
N3—C8—C9	114.2 (5)	C13—N2—Cu1	125.8 (4)
C7—C8—C9	124.3 (5)	C9—N2—Cu1	116.4 (4)
N2—C9—C10	123.0 (5)	C19—N3—C8	120.0 (5)
N2—C9—C8	114.4 (5)	C19—N3—Cu1	119.4 (3)
C10—C9—C8	122.6 (5)	C8—N3—Cu1	119.5 (4)
C9—C10—C11	119.0 (6)	C14—N4—C18	118.4 (5)
C9—C10—H10	120.5	C14—N4—Cu1	125.3 (4)
C11—C10—H10	120.5	C18—N4—Cu1	116.0 (4)