Di-μ-iodido-bis{[hydroxy(methoxy)bis(2-pyridyl)methane-κN,O,N']iodidocadmium(II)}.

In the centrosymmetric dinuclear title compound, [Cd(2)I(4)(C(12)H(12)N(2)O(2))(2)], two μ-I atoms bridge two Cd(II) atoms and each Cd(II) atom is also bonded to a terminal I atom and a hy-droxy-meth-oxy-bis-(2-pyrid-yl)methane ligand, which functions in an N,O,N'-tridentate mode, resulting in a distorted octa-hedral coordination environment. Inter-molecular O-H⋯I hydrogen bonds and π-π stacking inter-actions between the pyridine rings [centroid-centroid distance = 3.790 (2) Å] are present in the crystal structure.

Related literature

For general background to metal complexes with bis­(2-pyrid­yl)ketone or derivative ligands, see: Bandoli et al. (1994 ▶); Breeze et al. (1996 ▶); Crowder et al. (2004 ▶); Hemmert et al. (1999 ▶); Katsoulakou et al. (2002 ▶); Kavounis et al. (1996 ▶); Padhi & Sahu (2008 ▶); Papadopoulos et al. (1996 ▶); Rattanaphani & McWhinnie (1974 ▶); Serna et al. (2001 ▶); Sommerer et al. (1993 ▶); Tangoulis et al. (1997 ▶).

Experimental

Crystal data

[Cd2I4(C12H12N2O2)2]

M = 1164.89

Monoclinic,

a = 9.6684 (6) Å

b = 10.1083 (7) Å

c = 16.4970 (13) Å

β = 105.365 (5)°

V = 1554.64 (19) Å3

Z = 2

Mo Kα radiation

μ = 5.38 mm−1

T = 298 K

0.33 × 0.09 × 0.05 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.560, T max = 0.760

12218 measured reflections

4186 independent reflections

3589 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.056

S = 1.08

4186 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.69 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810041681/hy2362sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041681/hy2362Isup2.hkl

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

[Cd2I4(C12H12N2O2)2]	F(000) = 1072
Mr = 1164.89	Dx = 2.489 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 998 reflections
a = 9.6684 (6) Å	θ = 2.2–29.3°
b = 10.1083 (7) Å	µ = 5.38 mm−1
c = 16.4970 (13) Å	T = 298 K
β = 105.365 (5)°	Needle, colorless
V = 1554.64 (19) Å3	0.33 × 0.09 × 0.05 mm
Z = 2

Bruker APEX CCD diffractometer	4186 independent reflections
Radiation source: fine-focus sealed tube	3589 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 29.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.560, Tmax = 0.760	k = −13→13
12218 measured reflections	l = −22→22

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0193P)2 + 1.4317P] where P = (Fo2 + 2Fc2)/3
4186 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.69 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.1500 (4)	0.9278 (4)	−0.0544 (2)	0.0400 (8)
H1	0.2045	0.9914	−0.0726	0.048*
C2	0.0103 (4)	0.9080 (4)	−0.1006 (2)	0.0449 (9)
H2	−0.0289	0.9575	−0.1488	0.054*
C3	−0.0696 (4)	0.8134 (5)	−0.0738 (2)	0.0487 (10)
H3	−0.1637	0.7970	−0.1042	0.058*
C4	−0.0093 (4)	0.7425 (4)	−0.0012 (2)	0.0429 (8)
H4	−0.0622	0.6790	0.0182	0.051*
C5	0.1307 (3)	0.7683 (3)	0.0414 (2)	0.0321 (6)
C6	0.2084 (3)	0.6988 (3)	0.1231 (2)	0.0333 (7)
C7	0.3574 (5)	0.5630 (4)	0.0613 (3)	0.0546 (10)
H7A	0.3376	0.4787	0.0825	0.082*
H7B	0.4517	0.5619	0.0525	0.082*
H7C	0.2878	0.5808	0.0090	0.082*
C8	0.2258 (3)	0.7955 (3)	0.1957 (2)	0.0328 (7)
C9	0.1399 (4)	0.7896 (4)	0.2505 (2)	0.0425 (8)
H9	0.0728	0.7222	0.2462	0.051*
C10	0.1556 (4)	0.8853 (5)	0.3119 (2)	0.0499 (10)
H10	0.0983	0.8836	0.3492	0.060*
C11	0.2557 (5)	0.9825 (4)	0.3176 (2)	0.0469 (9)
H11	0.2684	1.0473	0.3590	0.056*
C12	0.3383 (4)	0.9825 (4)	0.2602 (2)	0.0409 (8)
H12	0.4066	1.0487	0.2640	0.049*
N1	0.2106 (3)	0.8594 (3)	0.01554 (17)	0.0330 (6)
N2	0.3235 (3)	0.8920 (3)	0.20032 (18)	0.0340 (6)
O1	0.3501 (2)	0.6642 (2)	0.12090 (16)	0.0373 (5)
O2	0.1277 (3)	0.5886 (3)	0.13179 (18)	0.0478 (6)
H2A	0.1654	0.5513	0.1763	0.072*
Cd1	0.45074 (2)	0.89825 (2)	0.095665 (15)	0.03330 (6)
I1	0.46360 (3)	1.17684 (2)	0.059856 (16)	0.03945 (6)
I2	0.71540 (3)	0.85526 (3)	0.213660 (16)	0.04384 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0416 (18)	0.044 (2)	0.0351 (17)	0.0046 (16)	0.0115 (14)	0.0072 (15)
C2	0.0449 (19)	0.057 (2)	0.0317 (17)	0.0187 (18)	0.0077 (15)	0.0028 (16)
C3	0.0281 (16)	0.075 (3)	0.0395 (19)	0.0080 (18)	0.0027 (14)	−0.0097 (19)
C4	0.0319 (16)	0.054 (2)	0.0418 (18)	−0.0047 (16)	0.0080 (14)	−0.0011 (17)
C5	0.0293 (15)	0.0334 (16)	0.0330 (15)	0.0016 (13)	0.0071 (12)	−0.0014 (13)
C6	0.0292 (14)	0.0314 (16)	0.0383 (17)	−0.0022 (13)	0.0073 (13)	0.0057 (14)
C7	0.061 (2)	0.040 (2)	0.061 (3)	0.0116 (19)	0.013 (2)	−0.0058 (19)
C8	0.0308 (15)	0.0351 (17)	0.0314 (15)	−0.0013 (13)	0.0062 (12)	0.0049 (13)
C9	0.0420 (18)	0.048 (2)	0.0395 (18)	−0.0023 (17)	0.0146 (15)	0.0121 (17)
C10	0.051 (2)	0.063 (3)	0.041 (2)	0.002 (2)	0.0227 (17)	0.0076 (19)
C11	0.061 (2)	0.048 (2)	0.0345 (18)	0.0048 (19)	0.0166 (17)	0.0008 (16)
C12	0.0429 (19)	0.0398 (19)	0.0408 (18)	−0.0067 (16)	0.0127 (15)	−0.0038 (16)
N1	0.0308 (13)	0.0369 (14)	0.0311 (13)	0.0025 (12)	0.0080 (11)	0.0040 (12)
N2	0.0334 (13)	0.0354 (15)	0.0344 (14)	−0.0026 (11)	0.0109 (11)	0.0015 (12)
O1	0.0343 (12)	0.0350 (12)	0.0400 (13)	0.0055 (10)	0.0054 (10)	0.0005 (10)
O2	0.0493 (15)	0.0385 (14)	0.0524 (16)	−0.0161 (12)	0.0080 (12)	0.0098 (12)
Cd1	0.02758 (11)	0.03613 (13)	0.03617 (12)	−0.00235 (9)	0.00842 (9)	0.00239 (10)
I1	0.04378 (12)	0.03060 (11)	0.04923 (13)	−0.00043 (9)	0.02155 (10)	−0.00408 (9)
I2	0.03782 (12)	0.04460 (14)	0.04293 (13)	0.00002 (10)	−0.00012 (9)	0.00529 (10)

C1—N1	1.340 (4)	C8—N2	1.346 (4)
C1—C2	1.378 (5)	C8—C9	1.383 (5)
C1—H1	0.9300	C9—C10	1.380 (6)
C2—C3	1.375 (6)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.365 (6)
C3—C4	1.384 (6)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.391 (5)
C4—C5	1.375 (5)	C11—H11	0.9300
C4—H4	0.9300	C12—N2	1.327 (4)
C5—N1	1.342 (4)	C12—H12	0.9300
C5—C6	1.529 (5)	Cd1—N1	2.381 (3)
C6—O2	1.389 (4)	Cd1—N2	2.371 (3)
C6—O1	1.424 (4)	Cd1—O1	2.633 (2)
C6—C8	1.520 (5)	O2—H2A	0.8200
C7—O1	1.433 (5)	Cd1—I1	2.8868 (4)
C7—H7A	0.9600	Cd1—I1i	2.9951 (4)
C7—H7B	0.9600	Cd1—I2	2.8082 (4)
C7—H7C	0.9600
N1—C1—C2	122.8 (4)	C11—C10—H10	120.2
N1—C1—H1	118.6	C9—C10—H10	120.2
C2—C1—H1	118.6	C10—C11—C12	118.5 (4)
C3—C2—C1	118.4 (3)	C10—C11—H11	120.7
C3—C2—H2	120.8	C12—C11—H11	120.7
C1—C2—H2	120.8	N2—C12—C11	122.6 (3)
C2—C3—C4	119.7 (3)	N2—C12—H12	118.7
C2—C3—H3	120.2	C11—C12—H12	118.7
C4—C3—H3	120.2	C1—N1—C5	118.1 (3)
C5—C4—C3	118.5 (4)	C1—N1—Cd1	122.2 (2)
C5—C4—H4	120.8	C5—N1—Cd1	119.7 (2)
C3—C4—H4	120.8	C12—N2—C8	118.6 (3)
N1—C5—C4	122.6 (3)	C12—N2—Cd1	123.3 (2)
N1—C5—C6	114.0 (3)	C8—N2—Cd1	118.0 (2)
C4—C5—C6	123.5 (3)	C6—O1—C7	114.5 (3)
O2—C6—O1	112.1 (3)	C6—O1—Cd1	100.48 (18)
O2—C6—C8	112.5 (3)	C7—O1—Cd1	116.5 (2)
O1—C6—C8	105.7 (3)	C6—O2—H2A	109.5
O2—C6—C5	107.5 (3)	N2—Cd1—N1	77.41 (9)
O1—C6—C5	110.0 (3)	N2—Cd1—O1	64.93 (9)
C8—C6—C5	108.9 (3)	N1—Cd1—O1	65.95 (8)
O1—C7—H7A	109.5	N2—Cd1—I2	92.54 (7)
O1—C7—H7B	109.5	N1—Cd1—I2	159.22 (7)
H7A—C7—H7B	109.5	O1—Cd1—I2	93.35 (5)
O1—C7—H7C	109.5	N2—Cd1—I1	103.52 (7)
H7A—C7—H7C	109.5	N1—Cd1—I1	97.81 (7)
H7B—C7—H7C	109.5	O1—Cd1—I1	161.21 (5)
N2—C8—C9	121.9 (3)	I2—Cd1—I1	102.242 (11)
N2—C8—C6	116.2 (3)	N2—Cd1—I1i	158.66 (7)
C9—C8—C6	121.8 (3)	N1—Cd1—I1i	86.16 (7)
C10—C9—C8	118.8 (4)	O1—Cd1—I1i	96.05 (5)
C10—C9—H9	120.6	I2—Cd1—I1i	98.429 (11)
C8—C9—H9	120.6	I1—Cd1—I1i	92.019 (9)
C11—C10—C9	119.6 (3)	Cd1—I1—Cd1i	87.981 (9)
N1—C1—C2—C3	−0.4 (6)	C8—C6—O1—Cd1	−60.1 (2)
C1—C2—C3—C4	1.0 (6)	C5—C6—O1—Cd1	57.4 (3)
C2—C3—C4—C5	−0.9 (6)	C12—N2—Cd1—N1	−131.9 (3)
C3—C4—C5—N1	0.2 (5)	C8—N2—Cd1—N1	44.4 (2)
C3—C4—C5—C6	178.8 (3)	C12—N2—Cd1—O1	159.0 (3)
N1—C5—C6—O2	−166.4 (3)	C8—N2—Cd1—O1	−24.7 (2)
C4—C5—C6—O2	14.9 (5)	C12—N2—Cd1—I2	66.5 (3)
N1—C5—C6—O1	−44.1 (4)	C8—N2—Cd1—I2	−117.2 (2)
C4—C5—C6—O1	137.2 (3)	C12—N2—Cd1—I1	−36.7 (3)
N1—C5—C6—C8	71.4 (3)	C8—N2—Cd1—I1	139.5 (2)
C4—C5—C6—C8	−107.3 (4)	C12—N2—Cd1—I1i	−172.4 (2)
O2—C6—C8—N2	168.1 (3)	C8—N2—Cd1—I1i	3.9 (4)
O1—C6—C8—N2	45.4 (4)	C1—N1—Cd1—N2	133.1 (3)
C5—C6—C8—N2	−72.7 (4)	C5—N1—Cd1—N2	−45.4 (2)
O2—C6—C8—C9	−15.8 (4)	C1—N1—Cd1—O1	−159.0 (3)
O1—C6—C8—C9	−138.5 (3)	C5—N1—Cd1—O1	22.5 (2)
C5—C6—C8—C9	103.4 (4)	C1—N1—Cd1—I2	−164.33 (19)
N2—C8—C9—C10	−0.2 (5)	C5—N1—Cd1—I2	17.2 (4)
C6—C8—C9—C10	−176.1 (3)	C1—N1—Cd1—I1	30.9 (3)
C8—C9—C10—C11	−0.6 (6)	C5—N1—Cd1—I1	−147.6 (2)
C9—C10—C11—C12	0.7 (6)	C1—N1—Cd1—I1i	−60.6 (3)
C10—C11—C12—N2	0.0 (6)	C5—N1—Cd1—I1i	120.9 (2)
C2—C1—N1—C5	−0.3 (5)	C6—O1—Cd1—N2	45.57 (19)
C2—C1—N1—Cd1	−178.8 (3)	C7—O1—Cd1—N2	169.9 (3)
C4—C5—N1—C1	0.4 (5)	C6—O1—Cd1—N1	−41.29 (19)
C6—C5—N1—C1	−178.3 (3)	C7—O1—Cd1—N1	83.0 (2)
C4—C5—N1—Cd1	179.0 (3)	C6—O1—Cd1—I2	136.82 (18)
C6—C5—N1—Cd1	0.3 (4)	C7—O1—Cd1—I2	−98.9 (2)
C11—C12—N2—C8	−0.8 (5)	C6—O1—Cd1—I1	−9.4 (3)
C11—C12—N2—Cd1	175.4 (3)	C7—O1—Cd1—I1	114.9 (3)
C9—C8—N2—C12	0.9 (5)	C6—O1—Cd1—I1i	−124.33 (18)
C6—C8—N2—C12	177.0 (3)	C7—O1—Cd1—I1i	0.0 (2)
C9—C8—N2—Cd1	−175.5 (3)	N2—Cd1—I1—Cd1i	−165.25 (7)
C6—C8—N2—Cd1	0.5 (4)	N1—Cd1—I1—Cd1i	−86.40 (7)
O2—C6—O1—C7	51.3 (4)	O1—Cd1—I1—Cd1i	−115.52 (17)
C8—C6—O1—C7	174.3 (3)	I2—Cd1—I1—Cd1i	99.076 (12)
C5—C6—O1—C7	−68.3 (4)	I1i—Cd1—I1—Cd1i	0.0
O2—C6—O1—Cd1	176.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···I2ii	0.82	2.73	3.509 (3)	160

Table 1

Selected bond lengths (Å)

Cd1—N1	2.381 (3)
Cd1—N2	2.371 (3)
Cd1—O1	2.633 (2)
Cd1—I1	2.8868 (4)
Cd1—I1i	2.9951 (4)
Cd1—I2	2.8082 (4)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯I2ii	0.82	2.73	3.509 (3)	160

Symmetry code: (ii) .