catena-Poly[[[1,2-bis­(benzimidazol-2-yl)ethane]cadmium(II)]-μ-sebacato]

Zhou, Y.-L.; Liang, H.; Zeng, M.-H.

doi:10.1107/S1600536810005714

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m405

doi:10.1107/S1600536810005714

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catena-Poly[[[1,2-bis(benzimidazol-2-yl)ethane]cadmium(II)]-μ-sebacato]

Yan-Ling Zhou,^a Hong Liang ^b and Ming-Hua Zeng ^b ^*

^aSchool of Chemistry and Chemical Engineering, Central South University, Changsha 410083, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin, 541004, People's Republic of China
^*Correspondence e-mail: zmh@mailbox.gxnu.edu.cn

(Received 29 January 2010; accepted 11 February 2010; online 13 March 2010)

In the title compound, [Cd(C₁₀H₁₆O₄)(C₁₆H₁₄N₄)]_n, the Cd^II ion is six-coordinated in a distorted octahedral geometry by four carboxylate O atoms from two sebacate ligands and two N atoms from the chelating 1,4-bis(2-benzimidazolyl)ethanebutane ligand. Neighboring Cd^II ions are bridged by the sebacate ligands, forming a zigzag polymeric chain structure. The chains are further extended into a three-dimensional supramolecular structure through intermolecular N—H⋯O hydrogen bonds.

Related literature

For the synthesis of the ligand, see: van Albada et al. (1995 ) and literature cited therein. For M–dicarboxylate complexes with aromatic N-donor chelating ligands, see: Wei et al. (2010 ) [M = lead(II) adduct]; Meng et al. (2008 ) [M = zinc(II) adduct]; Wang et al. (2006 ) [M = cadmium(II) and zinc(II) adducts].

Experimental

Crystal data

[Cd(C₁₀H₁₆O₄)(C₁₆H₁₄N₄)]
M_r = 574.95
Monoclinic, P 2₁ /c
a = 8.7554 (14) Å
b = 15.674 (3) Å
c = 18.455 (3) Å
β = 98.851 (3)°
V = 2502.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 110 K
0.48 × 0.34 × 0.27 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.669, T_max = 0.791
10665 measured reflections
4390 independent reflections
3533 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.096
S = 1.09
4390 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—N1	2.246 (3)
Cd1—N3	2.287 (3)
Cd1—O2	2.340 (3)
Cd1—O1	2.348 (3)
Cd1—O3	2.377 (3)
Cd1—O4	2.382 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.88	1.85	2.722 (4)	173
N4—H4A⋯O3ⁱⁱ	0.88	1.87	2.686 (4)	154
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005714/si2241sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005714/si2241Isup2.hkl

checkCIF report

Comment top

In recent years, studies on metal-dicarboxylate complexes with aromatic N-donor chelating ligands have attracted special attention because of their interesting structural and chemical properties (Wei et al., 2010; Meng et al., 2008; Wang et al., 2006). Herein, the title new cadmium-dicarboxylate complex, Fig. 1, is reported.

Selected bond distances are listed in Table 1. Each Cd(II) center is six-coordinated by two N atoms of the chelating 1,4-Bis(2-benzimidazolyl)ethanebutane ligand and four O atoms from two sebacate ligands. The neighboring Cd(II) ions are bridged by sebacate ligands to form a zigzag polymeric chain structure (Fig. 2). In the crystalstructure, the adjacent chains are linked via N—H···O hydrogen bonds (Table 2) resulting in the formation of a three-dimensional supramolecular structure.

Related literature top

For the synthesis of the ligand, see: van Albada et al. (1995) and literature cited therein. For M–dicarboxylate complexes with aromatic N-donor chelating ligands, see: Wei et al. (2010) [M = lead(II) adduct]; Meng et al. (2008) [M = zinc(II) adduct]; Wang et al. (2006) [M = cadmium(II) and zinc(II) adducts].

Experimental top

1,4-Bis(2-benzimidazolyl)ethanebutane was synthesized by using aliterature method (van Albada et al., 1995). A solution of Cd(NO₃)₂.6H₂O (0.17 g, 0.5 mmol), 1,4-Bis(2-benzimidazolyl)ethanebutane (0.13 g, 0.5 mmol), sebacic acid (0.10 g, 0.5 mmol), NaOH (0.02 g, 1 mmol) in H₂O (10 ml) and CH₃OH (5 ml) was stirred under ambient conditions, then sealed in a Teflon-lined steel vessel, heated at 443 K for 3 d, and cooled to room temperature. The resulting product was recovered by filtration, washed with distilled water and dried in air (35% yield).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).

catena-Poly[[[1,2-bis(benzimidazol-2-yl)ethane]cadmium(II)]- µ-sebacato] top

Crystal data top

[Cd(C₁₀H₁₆O₄)(C₁₆H₁₄N₄)]	F(000) = 1176
M_r = 574.95	D_x = 1.526 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5481 reflections
a = 8.7554 (14) Å	θ = 2.4–27.0°
b = 15.674 (3) Å	µ = 0.91 mm⁻¹
c = 18.455 (3) Å	T = 110 K
β = 98.851 (3)°	Block, yellow
V = 2502.4 (7) Å³	0.48 × 0.34 × 0.27 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4390 independent reflections
Radiation source: fine-focus sealed tube	3533 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
phi and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→6
T_min = 0.669, T_max = 0.791	k = −18→17
10665 measured reflections	l = −21→21

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.09	w = 1/[s²(F_o²) + (0.048P)² + 3.287P] where P = (F_o² + 2F_c²)/3
4390 reflections	(Δ/σ)_max < 0.001
316 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Cd(C₁₀H₁₆O₄)(C₁₆H₁₄N₄)]	V = 2502.4 (7) Å³
M_r = 574.95	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7554 (14) Å	µ = 0.91 mm⁻¹
b = 15.674 (3) Å	T = 110 K
c = 18.455 (3) Å	0.48 × 0.34 × 0.27 mm
β = 98.851 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4390 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3533 reflections with I > 2σ(I)
T_min = 0.669, T_max = 0.791	R_int = 0.026
10665 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.09	Δρ_max = 0.82 e Å⁻³
4390 reflections	Δρ_min = −0.44 e Å⁻³
316 parameters

Special details top

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
Cd1	0.09748 (3)	0.490930 (16)	0.300044 (14)	0.01805 (11)
N1	−0.1515 (4)	0.52080 (19)	0.25864 (16)	0.0194 (7)
N2	−0.4062 (4)	0.50949 (19)	0.25203 (17)	0.0203 (7)
H2A	−0.4966	0.4885	0.2581	0.024*
N3	0.0647 (4)	0.41909 (19)	0.40440 (16)	0.0181 (7)
N4	−0.0190 (3)	0.38418 (19)	0.50792 (15)	0.0190 (7)
H4A	−0.0836	0.3724	0.5387	0.023*
O1	0.1064 (3)	0.38258 (17)	0.21291 (15)	0.0269 (6)
O2	0.3259 (3)	0.43106 (16)	0.27181 (14)	0.0210 (6)
O3	0.1740 (3)	0.60960 (16)	0.37739 (13)	0.0217 (6)
O4	0.1927 (3)	0.62282 (16)	0.26098 (14)	0.0233 (6)
C1	−0.2210 (4)	0.5909 (2)	0.2205 (2)	0.0214 (8)
C2	−0.1571 (5)	0.6594 (3)	0.1866 (2)	0.0278 (9)
H2B	−0.0485	0.6645	0.1883	0.033*
C3	−0.2570 (5)	0.7191 (3)	0.1510 (2)	0.0299 (10)
H3A	−0.2164	0.7663	0.1278	0.036*
C4	−0.4171 (5)	0.7116 (3)	0.1481 (2)	0.0302 (10)
H4B	−0.4822	0.7544	0.1234	0.036*
C5	−0.4836 (5)	0.6447 (3)	0.1799 (2)	0.0272 (9)
H5A	−0.5924	0.6396	0.1773	0.033*
C6	−0.3813 (4)	0.5844 (2)	0.2163 (2)	0.0213 (8)
C7	−0.2672 (4)	0.4744 (2)	0.27599 (19)	0.0197 (8)
C8	−0.2521 (5)	0.3929 (2)	0.3185 (2)	0.0219 (8)
H8A	−0.1653	0.3598	0.3040	0.026*
H8B	−0.3476	0.3591	0.3045	0.026*
C9	−0.2244 (4)	0.4032 (2)	0.4013 (2)	0.0206 (8)
H9A	−0.2728	0.4573	0.4137	0.025*
H9B	−0.2777	0.3561	0.4230	0.025*
C10	−0.0578 (4)	0.4038 (2)	0.4366 (2)	0.0191 (8)
C11	0.1930 (4)	0.4077 (2)	0.46061 (19)	0.0176 (8)
C12	0.3508 (4)	0.4136 (2)	0.4588 (2)	0.0226 (9)
H12A	0.3884	0.4293	0.4150	0.027*
C13	0.4501 (5)	0.3963 (2)	0.5213 (2)	0.0224 (8)
H13A	0.5583	0.3992	0.5209	0.027*
C14	0.3941 (5)	0.3740 (2)	0.5875 (2)	0.0236 (9)
H14A	0.4658	0.3629	0.6306	0.028*
C15	0.2386 (5)	0.3684 (2)	0.5901 (2)	0.0220 (8)
H15A	0.2001	0.3537	0.6338	0.026*
C16	0.1396 (4)	0.3857 (2)	0.5243 (2)	0.0189 (8)
C17	0.2500 (5)	0.3857 (2)	0.2217 (2)	0.0212 (8)
C18	0.3369 (5)	0.3376 (2)	0.1691 (2)	0.0242 (9)
H18A	0.4488	0.3499	0.1815	0.029*
H18B	0.3220	0.2755	0.1749	0.029*
C19	0.2816 (5)	0.3627 (2)	0.0897 (2)	0.0271 (9)
H19A	0.3410	0.3303	0.0574	0.033*
H19B	0.1712	0.3472	0.0764	0.033*
C20	0.3008 (5)	0.4576 (3)	0.0773 (2)	0.0288 (9)
H20A	0.4098	0.4733	0.0949	0.035*
H20B	0.2356	0.4892	0.1075	0.035*
C21	0.2588 (5)	0.4865 (3)	−0.0021 (2)	0.0285 (9)
H21A	0.1521	0.4681	−0.0212	0.034*
H21B	0.3293	0.4589	−0.0322	0.034*
C22	0.2704 (5)	0.5833 (3)	−0.0092 (2)	0.0305 (10)
H22A	0.3746	0.6015	0.0142	0.037*
H22B	0.1944	0.6100	0.0183	0.037*
C23	0.2422 (5)	0.6172 (2)	−0.0878 (2)	0.0245 (9)
H23A	0.3248	0.5961	−0.1143	0.029*
H23B	0.1423	0.5949	−0.1132	0.029*
C24	0.2393 (5)	0.7145 (2)	−0.0905 (2)	0.0281 (9)
H24A	0.1541	0.7353	−0.0656	0.042*
H24B	0.3375	0.7366	−0.0631	0.042*
C25	0.2180 (5)	0.7502 (2)	0.3325 (2)	0.0225 (8)
H25A	0.1273	0.7789	0.3040	0.034*
H25B	0.3096	0.7666	0.3101	0.034*
C26	0.1956 (4)	0.6554 (2)	0.3231 (2)	0.0210 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.01791 (16)	0.02168 (16)	0.01482 (16)	−0.00217 (11)	0.00329 (10)	0.00041 (11)
N1	0.0207 (17)	0.0248 (17)	0.0121 (16)	−0.0036 (13)	0.0001 (13)	0.0008 (12)
N2	0.0156 (16)	0.0292 (18)	0.0161 (16)	−0.0049 (14)	0.0023 (13)	−0.0007 (13)
N3	0.0228 (17)	0.0168 (15)	0.0149 (16)	−0.0013 (13)	0.0036 (13)	0.0002 (12)
N4	0.0260 (19)	0.0199 (16)	0.0119 (16)	0.0022 (13)	0.0056 (14)	0.0031 (12)
O1	0.0209 (16)	0.0298 (15)	0.0292 (16)	−0.0017 (12)	0.0016 (12)	−0.0059 (12)
O2	0.0210 (14)	0.0223 (14)	0.0199 (14)	−0.0034 (11)	0.0036 (11)	−0.0037 (11)
O3	0.0284 (15)	0.0215 (14)	0.0164 (14)	−0.0031 (11)	0.0073 (11)	0.0033 (11)
O4	0.0301 (16)	0.0256 (14)	0.0146 (14)	−0.0033 (12)	0.0045 (12)	−0.0017 (11)
C1	0.026 (2)	0.022 (2)	0.0157 (19)	−0.0027 (16)	−0.0013 (16)	−0.0016 (15)
C2	0.025 (2)	0.031 (2)	0.027 (2)	−0.0058 (18)	0.0021 (17)	0.0037 (18)
C3	0.039 (3)	0.026 (2)	0.024 (2)	−0.0026 (19)	0.0026 (19)	0.0080 (17)
C4	0.034 (3)	0.029 (2)	0.027 (2)	0.0033 (19)	−0.0005 (19)	0.0054 (18)
C5	0.025 (2)	0.031 (2)	0.025 (2)	0.0014 (18)	0.0011 (17)	−0.0028 (17)
C6	0.025 (2)	0.022 (2)	0.017 (2)	0.0003 (16)	0.0022 (16)	−0.0020 (15)
C7	0.023 (2)	0.023 (2)	0.0126 (19)	−0.0032 (16)	0.0034 (16)	−0.0052 (15)
C8	0.024 (2)	0.022 (2)	0.020 (2)	−0.0056 (16)	0.0026 (16)	−0.0013 (15)
C9	0.023 (2)	0.022 (2)	0.017 (2)	−0.0033 (16)	0.0059 (16)	0.0019 (15)
C10	0.023 (2)	0.0124 (18)	0.022 (2)	−0.0009 (15)	0.0044 (16)	−0.0023 (15)
C11	0.024 (2)	0.0118 (17)	0.0165 (19)	−0.0007 (15)	0.0018 (16)	−0.0010 (14)
C12	0.027 (2)	0.0191 (19)	0.022 (2)	−0.0021 (16)	0.0049 (17)	0.0005 (15)
C13	0.022 (2)	0.022 (2)	0.022 (2)	0.0002 (16)	0.0012 (17)	−0.0042 (16)
C14	0.031 (2)	0.020 (2)	0.017 (2)	0.0055 (17)	−0.0016 (17)	−0.0012 (15)
C15	0.030 (2)	0.020 (2)	0.016 (2)	0.0039 (16)	0.0040 (17)	0.0028 (15)
C16	0.026 (2)	0.0159 (18)	0.0142 (19)	0.0006 (16)	0.0021 (16)	−0.0027 (14)
C17	0.026 (2)	0.0192 (19)	0.018 (2)	−0.0037 (16)	0.0015 (17)	0.0050 (15)
C18	0.026 (2)	0.022 (2)	0.025 (2)	0.0019 (17)	0.0020 (17)	−0.0034 (16)
C19	0.035 (2)	0.025 (2)	0.022 (2)	0.0052 (18)	0.0060 (18)	−0.0038 (17)
C20	0.036 (2)	0.023 (2)	0.026 (2)	0.0018 (18)	0.0038 (19)	0.0031 (17)
C21	0.038 (2)	0.030 (2)	0.017 (2)	0.0023 (19)	0.0010 (18)	0.0007 (16)
C22	0.045 (3)	0.026 (2)	0.019 (2)	0.0030 (19)	−0.0010 (19)	0.0012 (17)
C23	0.027 (2)	0.021 (2)	0.025 (2)	0.0038 (17)	0.0013 (17)	−0.0003 (16)
C24	0.037 (2)	0.022 (2)	0.024 (2)	0.0015 (18)	−0.0015 (19)	−0.0021 (16)
C25	0.022 (2)	0.026 (2)	0.019 (2)	−0.0033 (16)	0.0018 (16)	0.0029 (16)
C26	0.0127 (19)	0.026 (2)	0.023 (2)	−0.0023 (16)	0.0001 (15)	0.0007 (17)

Geometric parameters (Å, º) top

Cd1—N1	2.246 (3)	C9—H9B	0.9900
Cd1—N3	2.287 (3)	C11—C16	1.374 (5)
Cd1—O2	2.340 (3)	C11—C12	1.391 (5)
Cd1—O1	2.348 (3)	C12—C13	1.360 (5)
Cd1—O3	2.377 (3)	C12—H12A	0.9500
Cd1—O4	2.382 (3)	C13—C14	1.429 (5)
Cd1—C17	2.681 (4)	C13—H13A	0.9500
Cd1—C26	2.729 (4)	C14—C15	1.372 (5)
N1—C7	1.326 (5)	C14—H14A	0.9500
N1—C1	1.393 (5)	C15—C16	1.405 (5)
N2—C7	1.347 (5)	C15—H15A	0.9500
N2—C6	1.380 (5)	C17—C18	1.522 (5)
N2—H2A	0.8800	C18—C19	1.521 (5)
N3—C10	1.325 (5)	C18—H18A	0.9900
N3—C11	1.418 (5)	C18—H18B	0.9900
N4—C10	1.344 (5)	C19—C20	1.518 (5)
N4—C16	1.375 (5)	C19—H19A	0.9900
N4—H4A	0.8800	C19—H19B	0.9900
O1—C17	1.244 (5)	C20—C21	1.525 (6)
O2—C17	1.270 (4)	C20—H20A	0.9900
O3—C26	1.269 (4)	C20—H20B	0.9900
O4—C26	1.252 (4)	C21—C22	1.528 (5)
C1—C6	1.398 (5)	C21—H21A	0.9900
C1—C2	1.401 (5)	C21—H21B	0.9900
C2—C3	1.377 (6)	C22—C23	1.529 (5)
C2—H2B	0.9500	C22—H22A	0.9900
C3—C4	1.400 (6)	C22—H22B	0.9900
C3—H3A	0.9500	C23—C24	1.526 (5)
C4—C5	1.375 (6)	C23—H23A	0.9900
C4—H4B	0.9500	C23—H23B	0.9900
C5—C6	1.400 (6)	C24—C25ⁱ	1.509 (5)
C5—H5A	0.9500	C24—H24A	0.9900
C7—C8	1.494 (5)	C24—H24B	0.9900
C8—C9	1.519 (5)	C25—C26	1.506 (5)
C8—H8A	0.9900	C25—C24ⁱⁱ	1.509 (5)
C8—H8B	0.9900	C25—H25A	0.9900
C9—C10	1.503 (5)	C25—H25B	0.9900
C9—H9A	0.9900

N1—Cd1—N3	98.51 (11)	N4—C10—C9	120.3 (3)
N1—Cd1—O2	145.72 (10)	C16—C11—C12	120.5 (3)
N3—Cd1—O2	102.28 (10)	C16—C11—N3	108.8 (3)
N1—Cd1—O1	92.89 (10)	C12—C11—N3	130.7 (3)
N3—Cd1—O1	104.02 (10)	C13—C12—C11	118.3 (4)
O2—Cd1—O1	55.80 (9)	C13—C12—H12A	120.9
N1—Cd1—O3	102.14 (10)	C11—C12—H12A	120.9
N3—Cd1—O3	86.56 (9)	C12—C13—C14	121.0 (4)
O2—Cd1—O3	106.02 (9)	C12—C13—H13A	119.5
O1—Cd1—O3	160.22 (9)	C14—C13—H13A	119.5
N1—Cd1—O4	94.74 (10)	C15—C14—C13	121.2 (4)
N3—Cd1—O4	141.03 (10)	C15—C14—H14A	119.4
O2—Cd1—O4	85.97 (9)	C13—C14—H14A	119.4
O1—Cd1—O4	111.74 (9)	C14—C15—C16	116.2 (3)
O3—Cd1—O4	54.78 (8)	C14—C15—H15A	121.9
N1—Cd1—C17	118.86 (11)	C16—C15—H15A	121.9
N3—Cd1—C17	106.81 (11)	C11—C16—N4	106.3 (3)
O2—Cd1—C17	28.27 (10)	C11—C16—C15	122.8 (4)
O1—Cd1—C17	27.65 (10)	N4—C16—C15	130.9 (3)
O3—Cd1—C17	133.42 (10)	O1—C17—O2	121.5 (4)
O4—Cd1—C17	98.27 (10)	O1—C17—C18	119.5 (3)
N1—Cd1—C26	97.00 (11)	O2—C17—C18	119.0 (3)
N3—Cd1—C26	114.25 (11)	O1—C17—Cd1	61.1 (2)
O2—Cd1—C26	98.88 (10)	O2—C17—Cd1	60.75 (19)
O1—Cd1—C26	138.34 (10)	C18—C17—Cd1	171.1 (3)
O3—Cd1—C26	27.70 (10)	C19—C18—C17	111.7 (3)
O4—Cd1—C26	27.29 (10)	C19—C18—H18A	109.3
C17—Cd1—C26	119.61 (11)	C17—C18—H18A	109.3
C7—N1—C1	105.3 (3)	C19—C18—H18B	109.3
C7—N1—Cd1	122.8 (3)	C17—C18—H18B	109.3
C1—N1—Cd1	131.4 (2)	H18A—C18—H18B	107.9
C7—N2—C6	107.6 (3)	C20—C19—C18	111.8 (3)
C7—N2—H2A	126.2	C20—C19—H19A	109.3
C6—N2—H2A	126.2	C18—C19—H19A	109.3
C10—N3—C11	104.7 (3)	C20—C19—H19B	109.3
C10—N3—Cd1	133.0 (3)	C18—C19—H19B	109.3
C11—N3—Cd1	119.3 (2)	H19A—C19—H19B	107.9
C10—N4—C16	107.8 (3)	C19—C20—C21	114.8 (3)
C10—N4—H4A	126.1	C19—C20—H20A	108.6
C16—N4—H4A	126.1	C21—C20—H20A	108.6
C17—O1—Cd1	91.2 (2)	C19—C20—H20B	108.6
C17—O2—Cd1	91.0 (2)	C21—C20—H20B	108.6
C26—O3—Cd1	91.8 (2)	H20A—C20—H20B	107.5
C26—O4—Cd1	92.0 (2)	C20—C21—C22	111.6 (3)
N1—C1—C6	109.1 (3)	C20—C21—H21A	109.3
N1—C1—C2	131.1 (4)	C22—C21—H21A	109.3
C6—C1—C2	119.8 (4)	C20—C21—H21B	109.3
C3—C2—C1	117.8 (4)	C22—C21—H21B	109.3
C3—C2—H2B	121.1	H21A—C21—H21B	108.0
C1—C2—H2B	121.1	C21—C22—C23	115.1 (3)
C2—C3—C4	121.3 (4)	C21—C22—H22A	108.5
C2—C3—H3A	119.4	C23—C22—H22A	108.5
C4—C3—H3A	119.4	C21—C22—H22B	108.5
C5—C4—C3	122.4 (4)	C23—C22—H22B	108.5
C5—C4—H4B	118.8	H22A—C22—H22B	107.5
C3—C4—H4B	118.8	C24—C23—C22	112.2 (3)
C4—C5—C6	116.0 (4)	C24—C23—H23A	109.2
C4—C5—H5A	122.0	C22—C23—H23A	109.2
C6—C5—H5A	122.0	C24—C23—H23B	109.2
N2—C6—C1	105.5 (3)	C22—C23—H23B	109.2
N2—C6—C5	131.8 (4)	H23A—C23—H23B	107.9
C1—C6—C5	122.7 (4)	C25ⁱ—C24—C23	113.3 (3)
N1—C7—N2	112.5 (3)	C25ⁱ—C24—H24A	108.9
N1—C7—C8	125.9 (4)	C23—C24—H24A	108.9
N2—C7—C8	121.6 (3)	C25ⁱ—C24—H24B	108.9
C7—C8—C9	115.2 (3)	C23—C24—H24B	108.9
C7—C8—H8A	108.5	H24A—C24—H24B	107.7
C9—C8—H8A	108.5	C26—C25—C24ⁱⁱ	117.6 (3)
C7—C8—H8B	108.5	C26—C25—H25A	107.9
C9—C8—H8B	108.5	C24ⁱⁱ—C25—H25A	107.9
H8A—C8—H8B	107.5	C26—C25—H25B	107.9
C10—C9—C8	115.5 (3)	C24ⁱⁱ—C25—H25B	107.9
C10—C9—H9A	108.4	H25A—C25—H25B	107.2
C8—C9—H9A	108.4	O4—C26—O3	120.5 (3)
C10—C9—H9B	108.4	O4—C26—C25	119.4 (3)
C8—C9—H9B	108.4	O3—C26—C25	120.0 (3)
H9A—C9—H9B	107.5	O4—C26—Cd1	60.71 (19)
N3—C10—N4	112.4 (3)	O3—C26—Cd1	60.53 (19)
N3—C10—C9	127.3 (3)	C25—C26—Cd1	169.2 (3)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱⁱⁱ	0.88	1.85	2.722 (4)	173
N4—H4A···O3^iv	0.88	1.87	2.686 (4)	154

Symmetry codes: (iii) x−1, y, z; (iv) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cd(C₁₀H₁₆O₄)(C₁₆H₁₄N₄)]
M_r	574.95
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	110
a, b, c (Å)	8.7554 (14), 15.674 (3), 18.455 (3)
β (°)	98.851 (3)
V (Å³)	2502.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.48 × 0.34 × 0.27

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.669, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	10665, 4390, 3533
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.096, 1.09
No. of reflections	4390
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.44

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Cd1—N1	2.246 (3)	Cd1—O1	2.348 (3)
Cd1—N3	2.287 (3)	Cd1—O3	2.377 (3)
Cd1—O2	2.340 (3)	Cd1—O4	2.382 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.88	1.85	2.722 (4)	172.8
N4—H4A···O3ⁱⁱ	0.88	1.87	2.686 (4)	154.2

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

Acknowledgements

We thank Central South University and Guangxi Normal University for supporting this study.

References

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