Bis(1H-imidazole-κN3)bis­(1-naph­tha­lene­acetato-κ2O,O′)cadmium(II)

Song, W.-D.; Ji, L.-L.; Wu, Ho.-M.

doi:10.1107/S1600536808009409

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m653

doi:10.1107/S1600536808009409

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Bis(1H-imidazole-κN³)bis(1-naphthaleneacetato-κ²O,O′)cadmium(II)

Wen-Dong Song,^a ^* Li-Li Ji ^a and Hong-Mian Wu ^b

^aCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China, and ^bCollege of Food Science and Technology, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@126.com

(Received 25 March 2008; accepted 6 April 2008; online 10 April 2008)

In the mononuclear title compound, [Cd(C₁₂H₉O₂)₂(C₃H₄N₂)₂], the Cd^II centre has a distorted octahedral coordination geometry defined by four O atoms from two naphthaleneacetate ligands and two N atoms from two imidazole ligands. The molecules are linked by N—H⋯O hydrogen bonds, forming a layer network.

Related literature

For related literature, see: Duan et al. (2007 ); Liu et al. (2006 ).

Experimental

Crystal data

[Cd(C₁₂H₉O₂)₂(C₃H₄N₂)₂]
M_r = 618.95
Monoclinic, P 2₁ /n
a = 8.5275 (3) Å
b = 17.1596 (7) Å
c = 19.1198 (6) Å
β = 100.735 (2)°
V = 2748.81 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.84 mm⁻¹
T = 296 (2) K
0.26 × 0.23 × 0.21 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.812, T_max = 0.844
26061 measured reflections
5399 independent reflections
3336 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.142
S = 0.99
5399 reflections
340 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −1.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4ⁱ	0.86	1.92	2.735 (6)	159
N4—H4A⋯O2ⁱⁱ	0.86	1.95	2.772 (6)	159
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009409/ng2436sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009409/ng2436Isup2.hkl

checkCIF report

Comment top

naphthaleneacetate is nice ligand which has versatile bonding modes to metal ions and easily forms simple complexes (Liu et al., 2006; Duan et al., 2007). Recently, we obtained the mononuclear cadmium complex, (I), its crystal structure is reported here. Recently, we obtained the title novel mononuclear complex (I), by the reaction of cadmium chloride, 1-naphthylacetic acid and imidazole in an aqueous solution, and its crystal structure is reported here.

As depicted in Fig. 1, the Cd^II centre in (I) presents a distorted octahedral coordination geometry, defined by four O atoms from two 1-naphthaleneacetate ligands, and two N atoms from two imidazole ligands. The structural packing is governed by N—H···o hydrogen bonding interaction (Table 1) to form a layered network (Fig. 2).

Related literature top

For related literature, see: Duan et al. (2007); Liu et al. (2006).

Experimental top

The title complex was prepared by the addition of a stoichiometric amount of cadmium chloride (1 mmol) and imidazole (1 mmol) to a hot aqueous solution(10 ml) of 1-naphthylacetic acid (1 mmol). the pH was then adjusted to 7.0 to 8.0 with NaOH (1 mmol). The resulting solution was filtered, and colorlee single crystals were obtained at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing the atomic numbering scheme. Non-H atoms are shown as 30% probability displacement ellipsoids.
	Fig. 2. The packing of structure (I).

Bis(1H-imidazole-κN³)bis(1-naphthaleneacetato- κ²O,O')cadmium(II) top

Crystal data top

[Cd(C₁₂H₉O₂)₂(C₃H₄N₂)₂]	F(000) = 1256
M_r = 618.95	D_x = 1.496 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5300 reflections
a = 8.5275 (3) Å	θ = 1.3–28.0°
b = 17.1596 (7) Å	µ = 0.84 mm⁻¹
c = 19.1198 (6) Å	T = 296 K
β = 100.735 (2)°	Block, colorless
V = 2748.81 (17) Å³	0.26 × 0.23 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	5399 independent reflections
Radiation source: fine-focus sealed tube	3336 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
T_min = 0.812, T_max = 0.844	k = −16→21
26061 measured reflections	l = −23→23

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0533P)² + 1.0058P] where P = (F_o² + 2F_c²)/3
5399 reflections	(Δ/σ)_max = 0.001
340 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −1.16 e Å⁻³

Crystal data top

[Cd(C₁₂H₉O₂)₂(C₃H₄N₂)₂]	V = 2748.81 (17) Å³
M_r = 618.95	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5275 (3) Å	µ = 0.84 mm⁻¹
b = 17.1596 (7) Å	T = 296 K
c = 19.1198 (6) Å	0.26 × 0.23 × 0.21 mm
β = 100.735 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	5399 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3336 reflections with I > 2σ(I)
T_min = 0.812, T_max = 0.844	R_int = 0.089
26061 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 0.99	Δρ_max = 0.57 e Å⁻³
5399 reflections	Δρ_min = −1.16 e Å⁻³
340 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	0.3023 (7)	0.6405 (3)	0.3585 (3)	0.0583 (14)
C2	0.3810 (7)	0.6218 (4)	0.4342 (3)	0.0694 (16)
H2A	0.3450	0.6594	0.4656	0.083*
H2B	0.3449	0.5708	0.4463	0.083*
C3	0.5602 (7)	0.6219 (3)	0.4484 (2)	0.0581 (14)
C4	0.6434 (8)	0.6822 (3)	0.4844 (3)	0.0656 (16)
H4	0.5878	0.7224	0.5016	0.079*
C5	0.8115 (8)	0.6849 (3)	0.4962 (3)	0.0639 (15)
H5	0.8652	0.7265	0.5212	0.077*
C6	0.8959 (7)	0.6271 (3)	0.4713 (2)	0.0595 (14)
H6	1.0067	0.6297	0.4790	0.071*
C7	0.8159 (7)	0.5633 (3)	0.4339 (2)	0.0540 (13)
C8	0.9015 (7)	0.5033 (4)	0.4069 (3)	0.0649 (15)
H8	1.0124	0.5052	0.4145	0.078*
C9	0.8232 (9)	0.4431 (4)	0.3701 (3)	0.0785 (18)
H9	0.8802	0.4038	0.3525	0.094*
C10	0.6560 (9)	0.4402 (4)	0.3585 (4)	0.088 (2)
H10	0.6025	0.3991	0.3326	0.105*
C11	0.5716 (7)	0.4966 (4)	0.3845 (3)	0.0716 (16)
H11	0.4609	0.4927	0.3771	0.086*
C12	0.6464 (6)	0.5606 (3)	0.4223 (2)	0.0543 (13)
C13	0.2197 (7)	0.6142 (3)	0.1108 (2)	0.0593 (14)
C14	0.2727 (9)	0.5800 (4)	0.0458 (3)	0.0794 (19)
H14A	0.1911	0.5918	0.0046	0.095*
H14B	0.3691	0.6070	0.0394	0.095*
C15	0.3051 (9)	0.4945 (4)	0.0457 (3)	0.0718 (17)
C16	0.2010 (9)	0.4454 (4)	0.0041 (3)	0.092 (2)
H16	0.1081	0.4658	−0.0230	0.111*
C17	0.2301 (11)	0.3654 (5)	0.0011 (4)	0.101 (3)
H17	0.1559	0.3335	−0.0272	0.121*
C18	0.3651 (12)	0.3339 (5)	0.0390 (5)	0.102 (3)
H18	0.3832	0.2806	0.0361	0.122*
C19	0.4786 (9)	0.3811 (4)	0.0827 (3)	0.0738 (18)
C20	0.6198 (11)	0.3493 (5)	0.1221 (4)	0.091 (2)
H20	0.6394	0.2962	0.1192	0.109*
C21	0.7265 (12)	0.3946 (6)	0.1637 (4)	0.113 (3)
H21	0.8192	0.3730	0.1898	0.135*
C22	0.6983 (11)	0.4739 (6)	0.1678 (4)	0.108 (3)
H22	0.7731	0.5048	0.1968	0.129*
C23	0.5650 (10)	0.5074 (4)	0.1308 (3)	0.085 (2)
H23	0.5502	0.5608	0.1348	0.102*
C24	0.4467 (9)	0.4625 (3)	0.0858 (3)	0.0684 (18)
C25	−0.1907 (7)	0.6672 (3)	0.2707 (3)	0.0589 (14)
H25	−0.1394	0.6407	0.3110	0.071*
C26	−0.2362 (7)	0.7286 (3)	0.1729 (3)	0.0626 (15)
H26	−0.2210	0.7536	0.1315	0.075*
C27	−0.3772 (8)	0.7215 (4)	0.1936 (3)	0.0734 (16)
H27	−0.4758	0.7394	0.1699	0.088*
C28	0.2489 (10)	0.8574 (4)	0.2921 (3)	0.099 (3)
H28	0.2326	0.8398	0.3362	0.118*
C29	0.2722 (7)	0.8611 (3)	0.1845 (3)	0.0635 (15)
H29	0.2723	0.8466	0.1376	0.076*
C30	0.3157 (7)	0.9321 (4)	0.2124 (3)	0.0698 (16)
H30	0.3521	0.9743	0.1894	0.084*
Cd1	0.14721 (4)	0.68863 (2)	0.227269 (18)	0.05146 (17)
N1	0.2286 (6)	0.8142 (2)	0.2344 (2)	0.0604 (12)
N2	0.2951 (7)	0.9287 (3)	0.2801 (3)	0.0800 (15)
H2	0.3095	0.9664	0.3103	0.096*
N3	−0.1180 (5)	0.6943 (2)	0.2210 (2)	0.0542 (11)
N4	−0.3455 (6)	0.6822 (3)	0.2569 (3)	0.0648 (13)
H4A	−0.4137	0.6697	0.2829	0.078*
O1	0.1546 (5)	0.6372 (3)	0.3436 (2)	0.0823 (9)
O2	0.3806 (5)	0.6581 (3)	0.3125 (2)	0.0823 (9)
O3	0.2221 (6)	0.6855 (2)	0.1175 (2)	0.0803 (9)
O4	0.1694 (6)	0.5712 (2)	0.1548 (2)	0.0803 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.051 (4)	0.061 (4)	0.066 (3)	0.015 (3)	0.019 (3)	0.004 (3)
C2	0.059 (4)	0.093 (5)	0.059 (3)	0.003 (3)	0.016 (3)	0.003 (3)
C3	0.056 (4)	0.074 (4)	0.044 (3)	0.010 (3)	0.009 (3)	0.005 (3)
C4	0.073 (5)	0.074 (4)	0.048 (3)	0.014 (3)	0.006 (3)	−0.005 (3)
C5	0.076 (5)	0.064 (4)	0.048 (3)	−0.007 (3)	0.001 (3)	0.000 (3)
C6	0.054 (4)	0.064 (4)	0.057 (3)	−0.002 (3)	0.001 (3)	0.007 (3)
C7	0.056 (4)	0.062 (3)	0.043 (2)	0.004 (3)	0.005 (2)	0.012 (2)
C8	0.054 (4)	0.070 (4)	0.068 (3)	0.011 (3)	0.004 (3)	0.002 (3)
C9	0.076 (5)	0.069 (4)	0.089 (4)	0.020 (4)	0.012 (4)	−0.002 (3)
C10	0.088 (6)	0.067 (4)	0.101 (5)	0.003 (4)	0.002 (4)	−0.019 (4)
C11	0.054 (4)	0.075 (4)	0.081 (4)	−0.005 (3)	−0.001 (3)	−0.004 (3)
C12	0.050 (3)	0.061 (3)	0.051 (3)	0.002 (3)	0.006 (3)	0.005 (2)
C13	0.070 (4)	0.060 (4)	0.050 (3)	0.011 (3)	0.017 (3)	0.009 (2)
C14	0.109 (6)	0.077 (4)	0.061 (3)	0.011 (4)	0.036 (4)	0.007 (3)
C15	0.092 (5)	0.078 (4)	0.053 (3)	0.004 (4)	0.034 (3)	−0.011 (3)
C16	0.095 (6)	0.103 (6)	0.084 (4)	0.011 (5)	0.030 (4)	−0.037 (4)
C17	0.092 (6)	0.097 (6)	0.121 (6)	−0.013 (5)	0.038 (5)	−0.055 (5)
C18	0.118 (7)	0.078 (5)	0.130 (6)	−0.013 (5)	0.076 (6)	−0.036 (5)
C19	0.098 (6)	0.061 (4)	0.072 (4)	0.002 (4)	0.041 (4)	−0.009 (3)
C20	0.127 (7)	0.072 (5)	0.081 (4)	0.014 (5)	0.040 (5)	0.002 (4)
C21	0.145 (9)	0.113 (7)	0.080 (5)	0.028 (6)	0.019 (5)	0.005 (5)
C22	0.122 (8)	0.106 (7)	0.091 (5)	−0.014 (6)	0.007 (5)	−0.020 (5)
C23	0.120 (7)	0.065 (4)	0.074 (4)	−0.007 (5)	0.027 (4)	−0.002 (4)
C24	0.104 (5)	0.057 (4)	0.055 (3)	−0.010 (4)	0.043 (4)	−0.007 (3)
C25	0.046 (3)	0.070 (4)	0.063 (3)	0.003 (3)	0.014 (3)	0.011 (3)
C26	0.072 (4)	0.058 (3)	0.057 (3)	0.005 (3)	0.011 (3)	0.008 (3)
C27	0.056 (4)	0.079 (4)	0.080 (4)	−0.002 (3)	0.002 (3)	0.004 (4)
C28	0.166 (8)	0.062 (4)	0.088 (4)	−0.022 (4)	0.077 (5)	−0.009 (3)
C29	0.082 (4)	0.052 (4)	0.058 (3)	0.002 (3)	0.019 (3)	0.004 (3)
C30	0.079 (5)	0.059 (4)	0.076 (4)	0.003 (3)	0.028 (3)	0.010 (3)
Cd1	0.0507 (3)	0.0500 (3)	0.0565 (2)	−0.00004 (18)	0.01726 (19)	0.00188 (17)
N1	0.067 (3)	0.054 (3)	0.066 (3)	−0.004 (2)	0.029 (2)	−0.008 (2)
N2	0.106 (4)	0.050 (3)	0.094 (3)	−0.017 (3)	0.045 (3)	−0.014 (3)
N3	0.048 (3)	0.058 (3)	0.059 (2)	0.004 (2)	0.017 (2)	0.009 (2)
N4	0.053 (3)	0.071 (3)	0.074 (3)	−0.003 (2)	0.023 (2)	0.005 (2)
O1	0.0491 (18)	0.123 (3)	0.0752 (18)	0.0087 (18)	0.0131 (15)	0.0229 (18)
O2	0.0491 (18)	0.123 (3)	0.0752 (18)	0.0087 (18)	0.0131 (15)	0.0229 (18)
O3	0.125 (3)	0.0522 (18)	0.0756 (17)	0.0066 (17)	0.0499 (18)	0.0068 (14)
O4	0.125 (3)	0.0522 (18)	0.0756 (17)	0.0066 (17)	0.0499 (18)	0.0068 (14)

Geometric parameters (Å, º) top

C1—O2	1.236 (6)	C18—C19	1.412 (10)
C1—O1	1.240 (6)	C18—H18	0.9300
C1—C2	1.513 (7)	C19—C20	1.407 (9)
C2—C3	1.501 (8)	C19—C24	1.426 (8)
C2—H2A	0.9700	C20—C21	1.340 (11)
C2—H2B	0.9700	C20—H20	0.9300
C3—C4	1.366 (8)	C21—C22	1.386 (11)
C3—C12	1.425 (7)	C21—H21	0.9300
C4—C5	1.410 (9)	C22—C23	1.350 (10)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.362 (7)	C23—C24	1.423 (9)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.413 (7)	C25—N3	1.313 (6)
C6—H6	0.9300	C25—N4	1.323 (7)
C7—C8	1.414 (7)	C25—H25	0.9300
C7—C12	1.422 (7)	C26—C27	1.340 (8)
C8—C9	1.354 (8)	C26—N3	1.365 (7)
C8—H8	0.9300	C26—H26	0.9300
C9—C10	1.402 (9)	C27—N4	1.367 (8)
C9—H9	0.9300	C27—H27	0.9300
C10—C11	1.356 (8)	C28—N1	1.315 (7)
C10—H10	0.9300	C28—N2	1.319 (7)
C11—C12	1.402 (7)	C28—H28	0.9300
C11—H11	0.9300	C29—N1	1.352 (6)
C13—O3	1.230 (6)	C29—C30	1.355 (7)
C13—O4	1.252 (6)	C29—H29	0.9300
C13—C14	1.517 (7)	C30—N2	1.339 (7)
C14—C15	1.494 (8)	C30—H30	0.9300
C14—H14A	0.9700	Cd1—N3	2.244 (4)
C14—H14B	0.9700	Cd1—N1	2.259 (4)
C15—C16	1.367 (9)	Cd1—O3	2.306 (3)
C15—C24	1.415 (9)	Cd1—O1	2.384 (4)
C16—C17	1.398 (10)	Cd1—O2	2.384 (4)
C16—H16	0.9300	Cd1—O4	2.473 (4)
C17—C18	1.353 (11)	N2—H2	0.8600
C17—H17	0.9300	N4—H4A	0.8600

O2—C1—O1	120.6 (5)	C21—C20—H20	119.6
O2—C1—C2	122.0 (5)	C19—C20—H20	119.6
O1—C1—C2	117.4 (4)	C20—C21—C22	119.8 (9)
C3—C2—C1	115.3 (4)	C20—C21—H21	120.1
C3—C2—H2A	108.4	C22—C21—H21	120.1
C1—C2—H2A	108.4	C23—C22—C21	121.7 (8)
C3—C2—H2B	108.4	C23—C22—H22	119.1
C1—C2—H2B	108.4	C21—C22—H22	119.1
H2A—C2—H2B	107.5	C22—C23—C24	121.3 (7)
C4—C3—C12	118.8 (5)	C22—C23—H23	119.4
C4—C3—C2	120.5 (5)	C24—C23—H23	119.4
C12—C3—C2	120.6 (5)	C15—C24—C23	123.8 (6)
C3—C4—C5	121.5 (5)	C15—C24—C19	120.4 (6)
C3—C4—H4	119.3	C23—C24—C19	115.8 (7)
C5—C4—H4	119.3	N3—C25—N4	112.0 (5)
C6—C5—C4	120.5 (5)	N3—C25—H25	124.0
C6—C5—H5	119.7	N4—C25—H25	124.0
C4—C5—H5	119.7	C27—C26—N3	110.7 (5)
C5—C6—C7	120.3 (5)	C27—C26—H26	124.7
C5—C6—H6	119.8	N3—C26—H26	124.7
C7—C6—H6	119.8	C26—C27—N4	105.4 (6)
C6—C7—C8	121.1 (5)	C26—C27—H27	127.3
C6—C7—C12	119.0 (5)	N4—C27—H27	127.3
C8—C7—C12	119.9 (5)	N1—C28—N2	112.0 (5)
C9—C8—C7	120.5 (6)	N1—C28—H28	124.0
C9—C8—H8	119.8	N2—C28—H28	124.0
C7—C8—H8	119.8	N1—C29—C30	110.4 (5)
C8—C9—C10	119.9 (6)	N1—C29—H29	124.8
C8—C9—H9	120.1	C30—C29—H29	124.8
C10—C9—H9	120.1	N2—C30—C29	105.4 (5)
C11—C10—C9	120.7 (6)	N2—C30—H30	127.3
C11—C10—H10	119.7	C29—C30—H30	127.3
C9—C10—H10	119.7	N3—Cd1—N1	104.92 (16)
C10—C11—C12	121.8 (6)	N3—Cd1—O3	113.55 (17)
C10—C11—H11	119.1	N1—Cd1—O3	86.72 (14)
C12—C11—H11	119.1	N3—Cd1—O1	85.25 (14)
C11—C12—C7	117.2 (5)	N1—Cd1—O1	110.02 (16)
C11—C12—C3	123.0 (5)	O3—Cd1—O1	151.34 (16)
C7—C12—C3	119.8 (5)	N3—Cd1—O2	138.65 (14)
O3—C13—O4	121.1 (5)	N1—Cd1—O2	87.71 (17)
O3—C13—C14	117.9 (5)	O3—Cd1—O2	106.24 (15)
O4—C13—C14	121.0 (5)	O1—Cd1—O2	53.62 (13)
C15—C14—C13	117.6 (4)	N3—Cd1—O4	100.77 (15)
C15—C14—H14A	107.9	N1—Cd1—O4	139.07 (13)
C13—C14—H14A	107.9	O3—Cd1—O4	53.65 (12)
C15—C14—H14B	107.9	O1—Cd1—O4	103.32 (14)
C13—C14—H14B	107.9	O2—Cd1—O4	93.62 (16)
H14A—C14—H14B	107.2	C28—N1—C29	104.2 (5)
C16—C15—C24	118.3 (6)	C28—N1—Cd1	125.4 (4)
C16—C15—C14	120.4 (7)	C29—N1—Cd1	130.3 (3)
C24—C15—C14	121.3 (6)	C28—N2—C30	107.8 (5)
C15—C16—C17	121.9 (8)	C28—N2—H2	126.1
C15—C16—H16	119.1	C30—N2—H2	126.1
C17—C16—H16	119.1	C25—N3—C26	104.5 (5)
C18—C17—C16	120.7 (8)	C25—N3—Cd1	123.6 (4)
C18—C17—H17	119.6	C26—N3—Cd1	131.7 (3)
C16—C17—H17	119.6	C25—N4—C27	107.4 (5)
C17—C18—C19	120.5 (8)	C25—N4—H4A	126.3
C17—C18—H18	119.7	C27—N4—H4A	126.3
C19—C18—H18	119.7	C1—O1—Cd1	92.6 (3)
C20—C19—C18	121.2 (7)	C1—O2—Cd1	92.7 (3)
C20—C19—C24	120.6 (7)	C13—O3—Cd1	96.7 (3)
C18—C19—C24	118.2 (8)	C13—O4—Cd1	88.2 (3)
C21—C20—C19	120.8 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	1.92	2.735 (6)	159
N4—H4A···O2ⁱⁱ	0.86	1.95	2.772 (6)	159

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

Experimental details

Crystal data
Chemical formula	[Cd(C₁₂H₉O₂)₂(C₃H₄N₂)₂]
M_r	618.95
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.5275 (3), 17.1596 (7), 19.1198 (6)
β (°)	100.735 (2)
V (Å³)	2748.81 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.26 × 0.23 × 0.21

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.812, 0.844
No. of measured, independent and observed [I > 2σ(I)] reflections	26061, 5399, 3336
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.143, 0.99
No. of reflections	5399
No. of parameters	340
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −1.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	1.92	2.735 (6)	158.7
N4—H4A···O2ⁱⁱ	0.86	1.95	2.772 (6)	159.1

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

Acknowledgements

The authors acknowledge Guang Dong Ocean University for supporting this work.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Duan, J.-G., Liu, J.-W. & Wu, S. (2007). Acta Cryst. E63, m692–m694. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Liu, J.-W., Wang, W.-Y. & Gu, C.-S. (2006). Acta Cryst. E62, m3445–m3447. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar