Bis(acetato-κO)bis­(2-pyridine­aldoxime-κ2N,N′)cadmium

Shirvan, S.A.; Haydari Dezfuli, S.

doi:10.1107/S1600536812031819

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages m1080-m1081

https://doi.org/10.1107/S1600536812031819

Open

access

Bis(acetato-κO)bis(2-pyridinealdoxime-κ²N,N′)cadmium

Sadif A. Shirvan ^a ^* and Sara Haydari Dezfuli ^a

^aDepartment of Chemistry, Islamic Azad University, Omidieh Branch, Omidieh, Iran
^*Correspondence e-mail: sadif.shirvan1@gmail.com

(Received 25 June 2012; accepted 12 July 2012; online 18 July 2012)

In the title molecule, [Cd(CH₃COO)₂(C₆H₆N₂O)₂], the Cd^II cation is N,N′-chelated by two 2-pyridinealdoxime ligands and coordinated by two acetate anions in a distorted octahedral geometry. The hydroxy groups of the 2-pyridinealdoxime ligands link to the acetate anions via intramolecular O—H⋯O hydrogen bonds. Weak intermolecular C—H⋯O hydrogen bonds occur in the crystal.

Related literature

For related structures, see: Abu-Youssef et al. (2010 ); Costa et al. (2009 ); Ha (2010 ); Konidaris et al. (2010 ); Korpi et al. (2005 ); Milios et al. (2004 ); Mukherjee et al.(2009 ); Torabi et al. (2005 ).

Experimental

Crystal data

[Cd(C₂H₃O₂)₂(C₆H₆N₂O)₂]
M_r = 474.75
Triclinic, $[P \overline 1]$
a = 8.7875 (6) Å
b = 9.0946 (6) Å
c = 13.8873 (11) Å
α = 100.837 (6)°
β = 97.994 (6)°
γ = 114.700 (5)°
V = 960.42 (12) Å³
Z = 2
Mo Kα radiation
μ = 1.18 mm⁻¹
T = 298 K
0.48 × 0.38 × 0.30 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.621, T_max = 0.751
8165 measured reflections
3758 independent reflections
3236 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.084
S = 0.99
3758 reflections
252 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.96 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—N1	2.438 (3)
Cd1—N2	2.362 (3)
Cd1—N3	2.411 (3)
Cd1—N4	2.344 (3)
Cd1—O3	2.245 (3)
Cd1—O5	2.210 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O6	0.83 (2)	1.72 (1)	2.545 (4)	169 (4)
O2—H2B⋯O4	0.83 (5)	1.69 (5)	2.512 (5)	175 (6)
C6—H6A⋯O3ⁱ	0.93	2.52	3.381 (5)	153
C9—H9⋯O5ⁱⁱ	0.93	2.55	3.387 (6)	151
C12—H12A⋯O6ⁱⁱⁱ	0.93	2.56	3.264 (6)	132
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) x, y-1, z; (iii) x+1, y, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812031819/xu5584sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031819/xu5584Isup2.hkl

checkCIF report

Comment top

2-Pyridinealdoxime (pya), is a good bidentate ligand, and numerous complexes with pya have been prepared, such as that of manganese (Ha, 2010; Milios et al., 2004), rhenium (Costa et al., 2009), nickel (Mukherjee, et al., 2009), silver (Abu-Youssef et al., 2010), mercury (Torabi et al., 2005), zinc (Konidaris et al., 2010) and copper (Korpi et al., 2005). Here, we report the synthesis and structure of the title compound.

In the molecule of the title compound, (Fig. 1), the Cd^II atom is six-coordinated in a distorted octahedral configurations by four N atoms from two 2-pyridinealdoxime ligands and two O atom from two acetate anions. The Cd—O and Cd—N bond lengths and angles are collected in Table 1.

In the crystal structure, intermolecular O—H···O and C—H···O hydrogen bonds form a three-dimensional network (Table 2 & Fig. 2).

Related literature top

For related structures, see: Abu-Youssef et al. (2010); Costa et al. (2009); Ha (2010); Konidaris et al. (2010); Korpi et al. (2005); Milios et al. (2004); Mukherjee et al.(2009); Torabi et al. (2005).

Experimental top

A solution of 2-pyridinealdoxime (0.50 g, 4.0 mmol) in methanol (15 ml) was added to a solution of Cd(OAc)₂.2H₂O (0.54 g, 2.0 mmol) in methanol (15 ml) and the resulting colorless solution was stirred for 15 min at room temperature. This solution was left to evaporate slowly at room temperature. After one week, colorless prismatic crystals of the title compound were isolated (yield 0.69 g, 72.7%).

Structure description top

In the crystal structure, intermolecular O—H···O and C—H···O hydrogen bonds form a three-dimensional network (Table 2 & Fig. 2).

For related structures, see: Abu-Youssef et al. (2010); Costa et al. (2009); Ha (2010); Konidaris et al. (2010); Korpi et al. (2005); Milios et al. (2004); Mukherjee et al.(2009); Torabi et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Unit-cell packing diagram for title compound.

Bis(acetato-κO)bis(2-pyridinealdoxime- κ²N,N')cadmium(II) top

Crystal data top

[Cd(C₂H₃O₂)₂(C₆H₆N₂O)₂]	Z = 2
M_r = 474.75	F(000) = 476
Triclinic, P1	D_x = 1.642 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7875 (6) Å	Cell parameters from 8165 reflections
b = 9.0946 (6) Å	θ = 1.5–26.0°
c = 13.8873 (11) Å	µ = 1.18 mm⁻¹
α = 100.837 (6)°	T = 298 K
β = 97.994 (6)°	Prism, colorless
γ = 114.700 (5)°	0.48 × 0.38 × 0.30 mm
V = 960.42 (12) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3758 independent reflections
Radiation source: fine-focus sealed tube	3236 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.621, T_max = 0.751	k = −11→11
8165 measured reflections	l = −17→15

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0491P)²] where P = (F_o² + 2F_c²)/3
3758 reflections	(Δ/σ)_max = 0.010
252 parameters	Δρ_max = 0.64 e Å⁻³
2 restraints	Δρ_min = −0.95 e Å⁻³

Crystal data top

[Cd(C₂H₃O₂)₂(C₆H₆N₂O)₂]	γ = 114.700 (5)°
M_r = 474.75	V = 960.42 (12) Å³
Triclinic, P1	Z = 2
a = 8.7875 (6) Å	Mo Kα radiation
b = 9.0946 (6) Å	µ = 1.18 mm⁻¹
c = 13.8873 (11) Å	T = 298 K
α = 100.837 (6)°	0.48 × 0.38 × 0.30 mm
β = 97.994 (6)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3758 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3236 reflections with I > 2σ(I)
T_min = 0.621, T_max = 0.751	R_int = 0.056
8165 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	2 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.64 e Å⁻³
3758 reflections	Δρ_min = −0.95 e Å⁻³
252 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.8192 (5)	0.7991 (5)	0.9158 (3)	0.0581 (9)
H1	0.8759	0.8033	0.8639	0.070*
C2	0.8947 (6)	0.7893 (6)	1.0068 (3)	0.0722 (12)
H2	0.9992	0.7843	1.0152	0.087*
C3	0.8151 (6)	0.7869 (7)	1.0838 (4)	0.0845 (14)
H3	0.8653	0.7822	1.1460	0.101*
C4	0.6590 (6)	0.7916 (7)	1.0692 (3)	0.0781 (13)
H4	0.6029	0.7915	1.1213	0.094*
C5	0.5877 (5)	0.7965 (5)	0.9757 (3)	0.0570 (9)
C6	0.4177 (5)	0.7942 (5)	0.9549 (3)	0.0601 (9)
H6A	0.3628	0.8031	1.0067	0.072*
C7	0.3108 (5)	0.3972 (5)	0.6895 (3)	0.0564 (9)
H7	0.2298	0.4142	0.7203	0.068*
C8	0.2865 (6)	0.2340 (5)	0.6552 (3)	0.0672 (11)
H8	0.1925	0.1439	0.6637	0.081*
C9	0.4040 (6)	0.2086 (5)	0.6088 (4)	0.0731 (12)
H9	0.3917	0.1006	0.5853	0.088*
C10	0.5391 (6)	0.3433 (5)	0.5972 (3)	0.0686 (11)
H10	0.6188	0.3277	0.5643	0.082*
C11	0.5577 (4)	0.5027 (5)	0.6342 (3)	0.0508 (8)
C12	0.7043 (5)	0.6520 (5)	0.6258 (3)	0.0649 (11)
H12A	0.7859	0.6391	0.5939	0.078*
C13	0.8125 (7)	1.3947 (5)	0.8418 (4)	0.0858 (14)
H13A	0.8408	1.4150	0.9139	0.103*
H13B	0.7162	1.4160	0.8218	0.103*
H13C	0.9102	1.4682	0.8214	0.103*
C14	0.7660 (5)	1.2150 (5)	0.7920 (3)	0.0560 (9)
C15	0.0811 (5)	0.7410 (6)	0.4978 (3)	0.0698 (11)
H15A	0.1029	0.6727	0.4453	0.084*
H15B	0.1167	0.8513	0.4882	0.084*
H15C	−0.0400	0.6904	0.4955	0.084*
C16	0.1808 (5)	0.7544 (5)	0.5986 (3)	0.0540 (9)
N1	0.6675 (4)	0.8026 (4)	0.8998 (2)	0.0509 (7)
N2	0.3474 (4)	0.7801 (4)	0.8656 (2)	0.0520 (7)
N3	0.4438 (3)	0.5309 (3)	0.6806 (2)	0.0459 (6)
N4	0.7206 (4)	0.7966 (4)	0.6613 (2)	0.0519 (7)
O1	0.1873 (4)	0.7749 (5)	0.8529 (2)	0.0717 (8)
H1B	0.159 (5)	0.763 (5)	0.7912 (10)	0.058 (12)*
O2	0.8603 (4)	0.9252 (4)	0.6470 (3)	0.0863 (10)
H2B	0.864 (7)	1.016 (4)	0.675 (4)	0.11 (2)*
O3	0.6409 (4)	1.1036 (3)	0.8110 (2)	0.0700 (8)
O4	0.8568 (4)	1.1901 (4)	0.7372 (3)	0.0850 (9)
O5	0.3410 (3)	0.8162 (4)	0.6126 (2)	0.0682 (7)
O6	0.0997 (4)	0.7014 (5)	0.6609 (2)	0.0892 (10)
Cd1	0.51653 (3)	0.82333 (3)	0.745759 (18)	0.04330 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.062 (2)	0.063 (2)	0.051 (2)	0.0298 (19)	0.0140 (17)	0.0144 (18)
C2	0.072 (3)	0.082 (3)	0.066 (3)	0.042 (2)	0.006 (2)	0.019 (2)
C3	0.088 (3)	0.109 (4)	0.055 (3)	0.044 (3)	0.002 (2)	0.032 (3)
C4	0.087 (3)	0.106 (4)	0.045 (2)	0.045 (3)	0.015 (2)	0.026 (2)
C5	0.064 (2)	0.061 (2)	0.0416 (19)	0.0260 (18)	0.0115 (16)	0.0115 (17)
C6	0.066 (2)	0.073 (3)	0.046 (2)	0.032 (2)	0.0223 (17)	0.0176 (18)
C7	0.0511 (19)	0.058 (2)	0.054 (2)	0.0191 (17)	0.0148 (16)	0.0152 (18)
C8	0.069 (2)	0.054 (2)	0.064 (3)	0.0150 (19)	0.012 (2)	0.019 (2)
C9	0.088 (3)	0.048 (2)	0.077 (3)	0.030 (2)	0.012 (2)	0.013 (2)
C10	0.076 (3)	0.062 (2)	0.074 (3)	0.040 (2)	0.023 (2)	0.009 (2)
C11	0.0512 (18)	0.055 (2)	0.0488 (19)	0.0270 (16)	0.0140 (15)	0.0122 (16)
C12	0.060 (2)	0.071 (3)	0.074 (3)	0.034 (2)	0.036 (2)	0.018 (2)
C13	0.098 (3)	0.047 (2)	0.095 (4)	0.020 (2)	0.022 (3)	0.010 (2)
C14	0.065 (2)	0.053 (2)	0.045 (2)	0.0239 (18)	0.0067 (17)	0.0140 (17)
C15	0.062 (2)	0.092 (3)	0.059 (2)	0.038 (2)	0.0087 (19)	0.024 (2)
C16	0.051 (2)	0.055 (2)	0.057 (2)	0.0275 (17)	0.0068 (16)	0.0141 (17)
N1	0.0543 (16)	0.0539 (17)	0.0436 (16)	0.0251 (14)	0.0106 (13)	0.0112 (13)
N2	0.0485 (15)	0.0629 (19)	0.0475 (17)	0.0252 (14)	0.0201 (13)	0.0163 (14)
N3	0.0439 (14)	0.0479 (16)	0.0434 (15)	0.0199 (12)	0.0110 (11)	0.0097 (12)
N4	0.0469 (15)	0.0542 (17)	0.0562 (17)	0.0202 (13)	0.0243 (13)	0.0174 (14)
O1	0.0535 (15)	0.110 (2)	0.0619 (19)	0.0426 (16)	0.0251 (13)	0.0259 (18)
O2	0.0739 (19)	0.064 (2)	0.123 (3)	0.0204 (16)	0.064 (2)	0.026 (2)
O3	0.0821 (19)	0.0466 (15)	0.0721 (18)	0.0207 (14)	0.0283 (15)	0.0095 (14)
O4	0.094 (2)	0.0665 (19)	0.092 (2)	0.0296 (17)	0.0422 (19)	0.0197 (18)
O5	0.0527 (15)	0.088 (2)	0.0659 (18)	0.0314 (14)	0.0095 (12)	0.0301 (16)
O6	0.0664 (18)	0.136 (3)	0.0616 (18)	0.0385 (19)	0.0151 (15)	0.038 (2)
Cd1	0.04362 (14)	0.04697 (15)	0.04136 (15)	0.02141 (11)	0.01461 (9)	0.01174 (10)

Geometric parameters (Å, º) top

C1—N1	1.335 (5)	C12—N4	1.254 (5)
C1—C2	1.379 (6)	C12—H12A	0.9300
C1—H1	0.9300	C13—C14	1.502 (6)
C2—C3	1.357 (7)	C13—H13A	0.9600
C2—H2	0.9300	C13—H13B	0.9600
C3—C4	1.378 (7)	C13—H13C	0.9600
C3—H3	0.9300	C14—O4	1.235 (5)
C4—C5	1.377 (6)	C14—O3	1.246 (5)
C4—H4	0.9300	C15—C16	1.499 (5)
C5—N1	1.342 (5)	C15—H15A	0.9600
C5—C6	1.472 (5)	C15—H15B	0.9600
C6—N2	1.263 (5)	C15—H15C	0.9600
C6—H6A	0.9300	C16—O6	1.237 (5)
C7—N3	1.330 (5)	C16—O5	1.248 (4)
C7—C8	1.384 (6)	N2—O1	1.373 (4)
C7—H7	0.9300	N4—O2	1.367 (4)
C8—C9	1.366 (6)	O1—H1B	0.830 (10)
C8—H8	0.9300	O2—H2B	0.83 (5)
C9—C10	1.359 (6)	Cd1—N1	2.438 (3)
C9—H9	0.9300	Cd1—N2	2.362 (3)
C10—C11	1.376 (5)	Cd1—N3	2.411 (3)
C10—H10	0.9300	Cd1—N4	2.344 (3)
C11—N3	1.346 (4)	Cd1—O3	2.245 (3)
C11—C12	1.468 (6)	Cd1—O5	2.210 (3)

N1—C1—C2	122.3 (4)	O4—C14—C13	117.2 (4)
N1—C1—H1	118.8	O3—C14—C13	117.3 (4)
C2—C1—H1	118.8	C16—C15—H15A	109.5
C3—C2—C1	119.3 (4)	C16—C15—H15B	109.5
C3—C2—H2	120.3	H15A—C15—H15B	109.5
C1—C2—H2	120.3	C16—C15—H15C	109.5
C2—C3—C4	119.4 (4)	H15A—C15—H15C	109.5
C2—C3—H3	120.3	H15B—C15—H15C	109.5
C4—C3—H3	120.3	O6—C16—O5	124.8 (4)
C5—C4—C3	118.6 (4)	O6—C16—C15	118.3 (3)
C5—C4—H4	120.7	O5—C16—C15	116.9 (4)
C3—C4—H4	120.7	C1—N1—C5	118.0 (3)
N1—C5—C4	122.4 (4)	C1—N1—Cd1	127.0 (2)
N1—C5—C6	116.9 (3)	C5—N1—Cd1	115.0 (2)
C4—C5—C6	120.7 (4)	C6—N2—O1	115.0 (3)
N2—C6—C5	119.1 (3)	C6—N2—Cd1	118.9 (2)
N2—C6—H6A	120.4	O1—N2—Cd1	124.7 (2)
C5—C6—H6A	120.4	C7—N3—C11	117.1 (3)
N3—C7—C8	123.4 (4)	C7—N3—Cd1	127.8 (2)
N3—C7—H7	118.3	C11—N3—Cd1	115.0 (2)
C8—C7—H7	118.3	C12—N4—O2	115.3 (3)
C9—C8—C7	118.3 (4)	C12—N4—Cd1	118.4 (2)
C9—C8—H8	120.8	O2—N4—Cd1	126.3 (2)
C7—C8—H8	120.8	N2—O1—H1B	103 (3)
C10—C9—C8	119.2 (4)	N4—O2—H2B	109 (4)
C10—C9—H9	120.4	C14—O3—Cd1	129.1 (3)
C8—C9—H9	120.4	C16—O5—Cd1	124.6 (3)
C9—C10—C11	119.7 (4)	O5—Cd1—O3	95.55 (12)
C9—C10—H10	120.1	O5—Cd1—N4	96.42 (11)
C11—C10—H10	120.1	O3—Cd1—N4	100.57 (11)
N3—C11—C10	122.1 (4)	O5—Cd1—N2	103.25 (10)
N3—C11—C12	116.3 (3)	O3—Cd1—N2	91.65 (11)
C10—C11—C12	121.5 (3)	N4—Cd1—N2	155.72 (12)
N4—C12—C11	120.8 (3)	O5—Cd1—N3	92.09 (11)
N4—C12—H12A	119.6	O3—Cd1—N3	168.11 (10)
C11—C12—H12A	119.6	N4—Cd1—N3	69.45 (10)
C14—C13—H13A	109.5	N2—Cd1—N3	95.46 (10)
C14—C13—H13B	109.5	O5—Cd1—N1	170.71 (10)
H13A—C13—H13B	109.5	O3—Cd1—N1	89.02 (11)
C14—C13—H13C	109.5	N4—Cd1—N1	90.68 (10)
H13A—C13—H13C	109.5	N2—Cd1—N1	68.45 (10)
H13B—C13—H13C	109.5	N3—Cd1—N1	84.77 (10)
O4—C14—O3	125.5 (4)

N1—C1—C2—C3	−1.5 (7)	C14—O3—Cd1—N3	43.8 (7)
C1—C2—C3—C4	1.0 (8)	C14—O3—Cd1—N1	102.2 (4)
C2—C3—C4—C5	0.8 (8)	C12—N4—Cd1—O5	−92.2 (3)
C3—C4—C5—N1	−2.3 (7)	O2—N4—Cd1—O5	88.5 (3)
C3—C4—C5—C6	177.3 (4)	C12—N4—Cd1—O3	170.9 (3)
N1—C5—C6—N2	7.4 (6)	O2—N4—Cd1—O3	−8.4 (3)
C4—C5—C6—N2	−172.3 (4)	C12—N4—Cd1—N2	51.9 (4)
N3—C7—C8—C9	−0.9 (6)	O2—N4—Cd1—N2	−127.4 (4)
C7—C8—C9—C10	−0.4 (7)	C12—N4—Cd1—N3	−2.4 (3)
C8—C9—C10—C11	1.4 (7)	O2—N4—Cd1—N3	178.3 (4)
C9—C10—C11—N3	−1.2 (7)	C12—N4—Cd1—N1	81.8 (3)
C9—C10—C11—C12	178.3 (4)	O2—N4—Cd1—N1	−97.5 (3)
N3—C11—C12—N4	0.6 (6)	C6—N2—Cd1—O5	−172.9 (3)
C10—C11—C12—N4	−178.9 (4)	O1—N2—Cd1—O5	−7.2 (3)
C2—C1—N1—C5	0.1 (6)	C6—N2—Cd1—O3	−76.8 (3)
C2—C1—N1—Cd1	179.1 (3)	O1—N2—Cd1—O3	88.9 (3)
C4—C5—N1—C1	1.9 (6)	C6—N2—Cd1—N4	43.8 (5)
C6—C5—N1—C1	−177.8 (3)	O1—N2—Cd1—N4	−150.5 (3)
C4—C5—N1—Cd1	−177.3 (4)	C6—N2—Cd1—N3	93.6 (3)
C6—C5—N1—Cd1	3.0 (4)	O1—N2—Cd1—N3	−100.7 (3)
C5—C6—N2—O1	178.4 (3)	C6—N2—Cd1—N1	11.5 (3)
C5—C6—N2—Cd1	−14.5 (5)	O1—N2—Cd1—N1	177.2 (3)
C8—C7—N3—C11	1.1 (5)	C7—N3—Cd1—O5	−84.9 (3)
C8—C7—N3—Cd1	−175.4 (3)	C11—N3—Cd1—O5	98.6 (2)
C10—C11—N3—C7	0.0 (5)	C7—N3—Cd1—O3	145.1 (5)
C12—C11—N3—C7	−179.5 (3)	C11—N3—Cd1—O3	−31.4 (6)
C10—C11—N3—Cd1	176.9 (3)	C7—N3—Cd1—N4	179.1 (3)
C12—C11—N3—Cd1	−2.6 (4)	C11—N3—Cd1—N4	2.6 (2)
C11—C12—N4—O2	−178.7 (4)	C7—N3—Cd1—N2	18.7 (3)
C11—C12—N4—Cd1	2.0 (5)	C11—N3—Cd1—N2	−157.8 (2)
O4—C14—O3—Cd1	−6.0 (6)	C7—N3—Cd1—N1	86.4 (3)
C13—C14—O3—Cd1	175.2 (3)	C11—N3—Cd1—N1	−90.1 (2)
O6—C16—O5—Cd1	6.3 (6)	C1—N1—Cd1—O5	146.5 (6)
C15—C16—O5—Cd1	−172.3 (3)	C5—N1—Cd1—O5	−34.4 (7)
C16—O5—Cd1—O3	−111.5 (3)	C1—N1—Cd1—O3	−93.9 (3)
C16—O5—Cd1—N4	147.2 (3)	C5—N1—Cd1—O3	85.2 (3)
C16—O5—Cd1—N2	−18.5 (3)	C1—N1—Cd1—N4	6.7 (3)
C16—O5—Cd1—N3	77.6 (3)	C5—N1—Cd1—N4	−174.3 (3)
C16—O5—Cd1—N1	7.6 (8)	C1—N1—Cd1—N2	173.9 (3)
C14—O3—Cd1—O5	−85.9 (4)	C5—N1—Cd1—N2	−7.0 (3)
C14—O3—Cd1—N4	11.7 (4)	C1—N1—Cd1—N3	76.0 (3)
C14—O3—Cd1—N2	170.6 (3)	C5—N1—Cd1—N3	−105.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O6	0.83 (2)	1.72 (1)	2.545 (4)	169 (4)
O2—H2B···O4	0.83 (5)	1.69 (5)	2.512 (5)	175 (6)
C6—H6A···O3ⁱ	0.93	2.52	3.381 (5)	153
C9—H9···O5ⁱⁱ	0.93	2.55	3.387 (6)	151
C12—H12A···O6ⁱⁱⁱ	0.93	2.56	3.264 (6)	132

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x, y−1, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Cd(C₂H₃O₂)₂(C₆H₆N₂O)₂]
M_r	474.75
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.7875 (6), 9.0946 (6), 13.8873 (11)
α, β, γ (°)	100.837 (6), 97.994 (6), 114.700 (5)
V (Å³)	960.42 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.48 × 0.38 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.621, 0.751
No. of measured, independent and observed [I > 2σ(I)] reflections	8165, 3758, 3236
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.084, 0.99
No. of reflections	3758
No. of parameters	252
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.95

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—N1	2.438 (3)	Cd1—N4	2.344 (3)
Cd1—N2	2.362 (3)	Cd1—O3	2.245 (3)
Cd1—N3	2.411 (3)	Cd1—O5	2.210 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O6	0.831 (16)	1.724 (14)	2.545 (4)	169 (4)
O2—H2B···O4	0.83 (5)	1.69 (5)	2.512 (5)	175 (6)
C6—H6A···O3ⁱ	0.93	2.52	3.381 (5)	153
C9—H9···O5ⁱⁱ	0.93	2.55	3.387 (6)	151
C12—H12A···O6ⁱⁱⁱ	0.93	2.56	3.264 (6)	132

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x, y−1, z; (iii) x+1, y, z.

Acknowledgements

We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.

References

Abu-Youssef, M. A. M., Soliman, S. M., Langer, V., Gohar, Y. M., Hasanen, A. A., Makhyoun, M. A., Zaky, A. H. & Ohrstrom, L. R. (2010). Inorg. Chem. 49, 9788–9797. Web of Science CAS PubMed Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Costa, R., Barone, N., Gorczycka, C., Powers, E. F., Cupelo, W., Lopez, J., Herrick, R. S. & Ziegler, C. J. (2009). J. Organomet. Chem. 694, 2163–2170. Web of Science CSD CrossRef CAS Google Scholar
Ha, K. (2010). Z. Kristallogr. New Cryst. Struct. 225, 651–652. CAS Google Scholar
Konidaris, K. F., Katsoulakou, E., Kaplanis, M., Bekiari, V., Terzis, A., Raptopoulou, C. P., Zoupa, E. M. & Perlepes, S. P. (2010). Dalton Trans. 39, 4492–4494. Web of Science CSD CrossRef CAS PubMed Google Scholar
Korpi, H., Polamo, M., Leskela, M. & Repo, T. (2005). Inorg. Chem. Commun. 8, 1181–1184. Web of Science CSD CrossRef CAS Google Scholar
Milios, C. J., Kefalloniti, E., Raptopoulou, C. P., Terzis, A., Escuer, A., Vicente, R. & Perlepes, S. P. (2004). Polyhedron, 23, 83–95. Web of Science CSD CrossRef CAS Google Scholar
Mukherjee, S., Patel, B. A. & Bhaduri, S. (2009). Organometallics, 28, 3074–3078. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Torabi, A. A., Kian, R., Souldozi, A. & Welter, R. (2005). Z. Kristallogr. New Cryst. Struct. 220, 613–614. CAS Google Scholar