Di-μ-iodido-bis{[hydroxy(methoxy)bis(2-pyridyl)methane-κ3N,O,N′]iodidocadmium(II)}

Esmhosseini, M.; Safari, N.; Amani, V.

doi:10.1107/S1600536810041681

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages m1434-m1435

https://doi.org/10.1107/S1600536810041681

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Di-μ-iodido-bis{[hydroxy(methoxy)bis(2-pyridyl)methane-κ³N,O,N′]iodidocadmium(II)}

Majid Esmhosseini,^a ^* Nasser Safari ^b and Vahid Amani ^b

^aDepartment of Chemistry, University of Urmiyeh, Urmyieh, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: m.esmhosseini@urmia.ac.ir

(Received 3 October 2010; accepted 15 October 2010; online 23 October 2010)

In the centrosymmetric dinuclear title compound, [Cd₂I₄(C₁₂H₁₂N₂O₂)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 hydroxy-methoxy-bis(2-pyridyl)methane ligand, which functions in an N,O,N′-tridentate mode, resulting in a distorted octahedral coordination environment. Intermolecular O—H⋯I hydrogen bonds and π–π stacking interactions 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_r = 1164.89
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.056
S = 1.08
4186 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.69 e Å⁻³

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) -x+1, -y+2, -z.

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041681/hy2362Isup2.hkl

checkCIF report

Comment top

Bis(2-pyridyl)ketone (bpk) is a molecule that can exhibit different modes of coordination. As a bidentate ligand, it may present an N,O-coordination giving a five-membered chelate ring or an N,N-coordination forming a three or six-membered ring (Crowder et al., 2004; Rattanaphani & McWhinnie, 1974; Sommerer et al., 1993). Frequently the coordinated bpk undergoes nucleophilic addition of water or an alcohol at the carbonylic carbon atom to form the diol or the corresponding hemiacetal, (pyridyl)₂C(OR)(OH), which, deprotonated, acts as a mononegative, tridentate N,O,N-donor ligand. The three donor atoms may be coordinated to one metal atom (Bandoli et al., 1994; Crowder et al., 2004; Kavounis et al., 1996; Padhi & Sahu, 2008) or to two metal atoms in a bridging coordination (Breeze et al., 1996; Hemmert et al., 1999; Katsoulakou et al., 2002; Papadopoulos et al., 1996; Serna et al., 2001; Tangoulis et al., 1997). Here, we report the synthesis and structure of the title compound.

The asymmetric unit of the title compound contains a half of the molecule (Fig. 1). Two µ-I atoms bridge two Cd^II atoms, and each Cd^II atom is also bonded to a terminal I atom and an organic ligand which functions in an N,O,N'-tridentate mode, resulting in a distorted octahedral coordination environment. The Cd—I, Cd—O and Cd—N bond lengths are collected in Table 1.

In the crystal structure, intermolecular O—H···I hydrogen bonds (Table 2) and π–π interactions between the pyridine rings (Fig. 2), Cg···Cgⁱ [symmetry code: (i) -x, 2-y,-z; Cg is the centroid of the N1, C1–C5 ring], stabilize the structure, with a centroid-centroid distance of 3.790 (2) Å.

Related literature top

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 top

For the preparation of the title compound, a solution of bis(2-pyridyl)ketone (0.15 g, 0.80 mmol) in methanol (10 ml) was added to a solution of CdI₂ (0.29 g, 0.80 mmol) in methanol (5 ml) at room temperature. Crystals suitable for X-ray diffraction experiment were obtained by methanol diffusion into a colorless solution in DMSO. The crystals were isolated after one week (yield: 0.34 g, 72.9%).

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (a) 1-x, 2-y, -z.]
	Fig. 2. Packing diagram of the title compound. Dashed lines denote hydrogen bonds.

Di-µ-iodido-bis{[hydroxy(methoxy)bis(2-pyridyl)methane- κ³N,O,N']iodidocadmium(II)} top

Crystal data top

[Cd₂I₄(C₁₂H₁₂N₂O₂)₂]	F(000) = 1072
M_r = 1164.89	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0193P)² + 1.4317P] where P = (F_o² + 2F_c²)/3
4186 reflections	(Δ/σ)_max = 0.001
174 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Cd₂I₄(C₁₂H₁₂N₂O₂)₂]	V = 1554.64 (19) Å³
M_r = 1164.89	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6684 (6) Å	µ = 5.38 mm⁻¹
b = 10.1083 (7) Å	T = 298 K
c = 16.4970 (13) Å	0.33 × 0.09 × 0.05 mm
β = 105.365 (5)°

Data collection top

Bruker APEX CCD diffractometer	4186 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3589 reflections with I > 2σ(I)
T_min = 0.560, T_max = 0.760	R_int = 0.037
12218 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.056	H-atom parameters constrained
S = 1.08	Δρ_max = 0.61 e Å⁻³
4186 reflections	Δρ_min = −0.69 e Å⁻³
174 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cd₂I₄(C₁₂H₁₂N₂O₂)₂]
M_r	1164.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.6684 (6), 10.1083 (7), 16.4970 (13)
β (°)	105.365 (5)
V (Å³)	1554.64 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	5.38
Crystal size (mm)	0.33 × 0.09 × 0.05

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.560, 0.760
No. of measured, independent and observed [I > 2σ(I)] reflections	12218, 4186, 3589
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.056, 1.08
No. of reflections	4186
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.69

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

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

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2.

Acknowledgements

We are grateful to the University of Urmiyeh and Shahid Beheshti University for financial support.

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