Bis(μ-2-hydroxy­benozato)-κ3O,O′:O′;κ3O:O,O′-bis­[(2-hydroxy­benozato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)cadmium(II)]

Shi, Q.-Y.; Li, Z.-C.; Cheng, Z.-S.; Tan, J.-B.; Liu, J.-L.

doi:10.1107/S1600536808033886

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1458

doi:10.1107/S1600536808033886

Open

access

Bis(μ-2-hydroxybenozato)-κ³O,O′:O′;κ³O:O,O′-bis[(2-hydroxybenozato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)cadmium(II)]

Qing-Yuan Shi,^a ^* Zhi-Cheng Li,^a Zong-Sheng Cheng,^a Jing-Bo Tan ^a and Jia-Lun Liu ^a

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: fanj@scnu.edu.cn

(Received 25 September 2008; accepted 17 October 2008; online 25 October 2008)

The dinuclear title compound, [Cd₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂], is located on a crystallographic rotation twofold axis. The two Cd^II ions are connected by two tridentate bridging 2-hydroxybenzoate anions. Each Cd^II ion is seven-coordinated by five O atoms from three 2-hydroxybenzoate ligands and two N atoms from 1,10-phenanthroline. The 2-hydroxybenzoate molecules adopt two kinds of coordination mode, bidentate chelating and tridentate bridging–chelating. Intramolecular hydrogen bonds between hydroxy and carboxylate groups from 2-hydroxybenzoate groups and π–π stacking interactions between parallel 1,10-phenanthroline ligands [centroid–centroid distances = 3.707 (3) and 3.842 (3) Å] are observed. Furthermore, adjacent benzene rings from 2-hydroxybenzoate ligands are involved in π–π interactions with interplanar distances of 3.642 (3) Å, thereby forming a chain along the a axis direction.

Related literature

For general background, see: Horike et al. (2007 ); Humphrey et al. (2007 ); Sudik et al. (2005 ); Zhang et al. (2008 ). For related structures, see: Du et al. (2007 ); Pan et al. (2006 ); Tomas et al. (2006 ). For related literature, see: Tong et al. (1999 )

Experimental

Crystal data

[Cd₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂]
M_r = 1133.65
Monoclinic, C 2/c
a = 27.9391 (19) Å
b = 10.3078 (7) Å
c = 20.468 (2) Å
β = 130.770 (1)°
V = 4464.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 298 (2) K
0.30 × 0.25 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.748, T_max = 0.837
11963 measured reflections
4390 independent reflections
3671 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.067
S = 1.06
4390 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O4	0.82	1.86	2.579 (3)	146
O3—H3A⋯O2	0.82	1.87	2.576 (2)	143

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 1999 ); 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) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033886/zl2145sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033886/zl2145Isup2.hkl

checkCIF report

Comment top

Transition metal complexes with substituted benzoate ligands have attracted wide attention in past decades, owing to their variable high-dimensional architectures and potential applications for gas absorption and separation, and catalysis, etc [Du et al., 2007; Horike et al., 2007; Humphrey et al., 2007; Pan et al., 2006; Sudik et al., 2005; Tomas et al., 2006; Zhang et al., 2008]. Herein, we report the synthesis and crystal structure of the title compound, obtained by the reaction of Sm(NO₃)₃, Cd(CH₃COO)₂, 1,10-phenanthroline and 2-hydroxybenzoic acid. No samarium was however incorporated in the crystals isolated and the title compound is a dinuclear Cd^II complex of 2-hydroxybenzoic acid and 1,10-phenanthroline. A perspective view of the complex, showing the atomic numbering scheme, is depicted in Fig. 1. Each Cd^II is seven-coordinated by five oxygen atoms from three 2-hydroxybenzoate ligands, and two nitrogen atoms from 1,10-phenanthroline, and the coordination geometry around the Cd^II ion may be described as a distorted mono-capped trigonal prism. Two adjacent Cd^II units are connected by two bridging 2-hydroxybenzoate anions to generate a dinuclear complex. The 2-hydroxybenzoate molecules adopt two kinds of coordination modes, bidentate chelating and tridentate bridging-chelating. The inequivalence between the mono and bidentate bridging oxygen atoms is evident from the Cd—O bond distances: the Cd—O distances of the bridging oxygen atoms are longer than those of the monodentate oxygen atoms: Cd1—O5 is 2.421 (2) Å and Cd1—O5ⁱ is 2.491 (2) Å, while Cd1—O1, Cd—O2 and Cd—O4 are 2.399 (2), 2.327 (2) and 2.363 (2) Å, respectively (symmetry code: (i): -x, y, 1/2 - z).

Intramolecular hydrogen bonds between hydroxyl and carboxylate groups from the 2-hydroxybenzoates [O6···O4 = 2.579 (3) Å and O3···O2 = 2.576 (2) Å, Table 1] and π-π stacking attractions between parallel 1,10-phenanthroline ligands [centroid to centroid distances: 3.707 (3) and 3.842 (3) Å] are clearly observed in this complex, which may contribute to its stability.

Furthermore, adjacent phenyl rings from 2-hydroxybenzoate ligands are also involved in π-π stacking interactions by partial overlap of π-electron densities (Tong et al., 1999). The centroid-centroid separation between rings A (atoms C14—C19) and B^j [atoms C21—C26; symmetry code: (j): 1/2 + x, 1/2 - y, 1/2 + z] is 3.642 (3) Å. Considering these π-π intermolecular attractions, they imply the formation of a one-dimensional chain along the direction of the a-axis. (Fig. 2).

Related literature top

For general background, see: Horike et al. (2007); Humphrey et al. (2007); Sudik et al. (2005); Zhang et al. (2008). For related structures, see: Du et al. (2007); Pan et al. (2006); Tomas et al. (2006). For related literature, see: Tong et al. (1999).

Experimental top

A sample of Sm(NO₃)₃.6H₂O (0.090 g, 0.20 mmol), Cd(CH₃COO)₂.2H₂O (0.052 g, 0.20 mmol), 2-hydroxybenzoic acid (0.070 g, 0.50 mmol), 1,10-phenanthroline (0.036 g, 0.20 mmol) and distilled water (8 ml) were mixed in a 15 ml Teflon-lined stainless steel vessel and the pH value was adjusted to about 5 with NaOH. Then, the mixture was heated to 393 K under autogenous pressure for 48 h, and cooled slowly to room temperature. Colorless block-like crystals suitable for X-ray single-crystal diffraction analysis were obtained by filtration and washed with distilled water and ethanol.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. An ORTEP-3 (Farrugia, 1997) plot of the title compound with displacement ellipsoids at the 30% probability level. All H atoms are omitted for clarity.
	Fig. 2. A packing diagram of the title compound, showing a one-dimensional chain-like structure generated by the intermolecular π-π interactions. All H atoms are omitted for clarity. [Symmetry codes: (j): 1/2 + x, 1/2 - y, 1/2 + z].

Bis(µ-2-hydroxybenozato)- κ³O,O':O';κ³O:O,O'- bis[(2-hydroxybenozato-κ²O,O')(1,10-phenanthroline- κ²N,N')cadmium(II)] top

Crystal data top

[Cd₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂]	F(000) = 2272
M_r = 1133.65	D_x = 1.687 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4082 reflections
a = 27.9391 (19) Å	θ = 1.9–27.4°
b = 10.3078 (7) Å	µ = 1.03 mm⁻¹
c = 20.468 (2) Å	T = 298 K
β = 130.770 (1)°	Block, colorless
V = 4464.2 (6) Å³	0.30 × 0.25 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4390 independent reflections
Radiation source: fine-focus sealed tube	3671 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→23
T_min = 0.748, T_max = 0.837	k = −12→12
11963 measured reflections	l = −18→25

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0314P)² + 1.2193P] where P = (F_o² + 2F_c²)/3
4390 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cd₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂]	V = 4464.2 (6) Å³
M_r = 1133.65	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 27.9391 (19) Å	µ = 1.03 mm⁻¹
b = 10.3078 (7) Å	T = 298 K
c = 20.468 (2) Å	0.30 × 0.25 × 0.18 mm
β = 130.770 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4390 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3671 reflections with I > 2σ(I)
T_min = 0.748, T_max = 0.837	R_int = 0.027
11963 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.06	Δρ_max = 0.25 e Å⁻³
4390 reflections	Δρ_min = −0.36 e Å⁻³
316 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	0.13185 (12)	0.5408 (3)	0.40308 (16)	0.0477 (6)
H1	0.1436	0.4625	0.4326	0.057*
C2	0.15571 (15)	0.6556 (3)	0.4506 (2)	0.0609 (8)
H2	0.1832	0.6534	0.5105	0.073*
C3	0.13835 (14)	0.7702 (3)	0.40838 (19)	0.0644 (8)
H3	0.1536	0.8474	0.4394	0.077*
C4	0.09731 (13)	0.7733 (3)	0.31771 (18)	0.0491 (7)
C5	0.07771 (16)	0.8903 (3)	0.2685 (2)	0.0652 (9)
H5	0.0920	0.9697	0.2971	0.078*
C6	0.03932 (15)	0.8881 (3)	0.1826 (2)	0.0604 (8)
H6	0.0278	0.9657	0.1524	0.072*
C7	0.01567 (12)	0.7686 (2)	0.13628 (17)	0.0448 (6)
C8	−0.02500 (12)	0.7611 (3)	0.04561 (18)	0.0517 (7)
H8	−0.0379	0.8367	0.0131	0.062*
C9	−0.04538 (13)	0.6440 (3)	0.00554 (18)	0.0510 (7)
H9	−0.0719	0.6383	−0.0542	0.061*
C10	−0.02569 (11)	0.5324 (3)	0.05582 (16)	0.0438 (6)
H10	−0.0399	0.4524	0.0281	0.053*
C11	0.03313 (11)	0.6513 (2)	0.18132 (16)	0.0352 (5)
C12	0.07583 (11)	0.6531 (2)	0.27488 (16)	0.0362 (5)
C13	0.16216 (11)	0.2707 (2)	0.25844 (15)	0.0393 (6)
C14	0.22134 (11)	0.2278 (2)	0.27919 (16)	0.0407 (6)
C15	0.26018 (13)	0.1335 (3)	0.34283 (19)	0.0518 (7)
C16	0.31708 (14)	0.1016 (3)	0.3645 (2)	0.0701 (9)
H16	0.3431	0.0400	0.4071	0.084*
C17	0.33538 (17)	0.1594 (4)	0.3243 (3)	0.0817 (12)
H17	0.3737	0.1362	0.3395	0.098*
C18	0.29839 (16)	0.2517 (4)	0.2617 (3)	0.0750 (10)
H18	0.3114	0.2908	0.2346	0.090*
C19	0.24122 (14)	0.2856 (3)	0.2392 (2)	0.0558 (7)
H19	0.2159	0.3480	0.1969	0.067*
C20	−0.05515 (11)	0.2173 (2)	0.10588 (15)	0.0382 (5)
C21	−0.11314 (11)	0.1442 (2)	0.03654 (15)	0.0361 (5)
C22	−0.11635 (12)	0.0730 (2)	−0.02440 (15)	0.0432 (6)
C23	−0.17163 (14)	0.0033 (3)	−0.08804 (16)	0.0565 (8)
H23	−0.1743	−0.0454	−0.1285	0.068*
C24	−0.22170 (13)	0.0073 (3)	−0.09029 (18)	0.0607 (8)
H24	−0.2581	−0.0396	−0.1324	0.073*
C25	−0.21937 (13)	0.0784 (3)	−0.03221 (18)	0.0576 (8)
H25	−0.2541	0.0811	−0.0353	0.069*
C26	−0.16526 (12)	0.1463 (2)	0.03120 (17)	0.0451 (6)
H26	−0.1636	0.1944	0.0711	0.054*
Cd1	0.057575 (8)	0.350425 (15)	0.231588 (11)	0.03562 (7)
N1	0.09300 (9)	0.53845 (19)	0.31732 (12)	0.0372 (4)
N2	0.01241 (8)	0.53497 (18)	0.14148 (12)	0.0361 (4)
O1	0.13009 (8)	0.36071 (17)	0.20625 (12)	0.0517 (5)
O2	0.14511 (8)	0.21631 (18)	0.29634 (11)	0.0497 (5)
O3	0.24496 (10)	0.0733 (2)	0.38541 (14)	0.0733 (6)
H3A	0.2083	0.0907	0.3625	0.110*
O4	−0.00846 (8)	0.21515 (17)	0.10927 (12)	0.0527 (5)
O5	0.05244 (8)	0.28218 (18)	0.34009 (12)	0.0516 (5)
O6	−0.06878 (9)	0.06944 (18)	−0.02577 (12)	0.0582 (5)
H6A	−0.0397	0.1157	0.0128	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0451 (14)	0.0544 (16)	0.0402 (15)	0.0009 (12)	0.0264 (12)	0.0023 (12)
C2	0.0598 (19)	0.074 (2)	0.0388 (15)	−0.0100 (15)	0.0276 (14)	−0.0083 (14)
C3	0.075 (2)	0.0561 (19)	0.0585 (19)	−0.0184 (16)	0.0419 (17)	−0.0227 (15)
C4	0.0547 (16)	0.0434 (15)	0.0540 (17)	−0.0046 (12)	0.0375 (14)	−0.0069 (12)
C5	0.083 (2)	0.0347 (15)	0.079 (2)	−0.0069 (15)	0.0531 (19)	−0.0092 (15)
C6	0.081 (2)	0.0320 (14)	0.074 (2)	0.0066 (14)	0.0534 (19)	0.0109 (14)
C7	0.0488 (14)	0.0373 (14)	0.0556 (16)	0.0067 (11)	0.0373 (13)	0.0082 (12)
C8	0.0521 (16)	0.0519 (17)	0.0555 (17)	0.0147 (13)	0.0370 (14)	0.0210 (14)
C9	0.0466 (15)	0.0615 (19)	0.0398 (15)	0.0083 (13)	0.0260 (13)	0.0099 (13)
C10	0.0407 (13)	0.0445 (14)	0.0398 (14)	0.0001 (11)	0.0235 (12)	0.0003 (11)
C11	0.0358 (12)	0.0347 (13)	0.0438 (14)	0.0014 (9)	0.0298 (12)	0.0025 (10)
C12	0.0361 (12)	0.0362 (13)	0.0426 (14)	−0.0019 (10)	0.0284 (11)	−0.0020 (10)
C13	0.0359 (13)	0.0407 (14)	0.0367 (13)	−0.0027 (10)	0.0217 (11)	−0.0052 (11)
C14	0.0380 (13)	0.0415 (14)	0.0453 (14)	−0.0039 (10)	0.0284 (12)	−0.0091 (11)
C15	0.0413 (15)	0.0504 (17)	0.0551 (17)	0.0027 (12)	0.0277 (14)	−0.0097 (13)
C16	0.0430 (16)	0.072 (2)	0.079 (2)	0.0128 (15)	0.0329 (17)	−0.0067 (18)
C17	0.052 (2)	0.089 (3)	0.110 (3)	−0.0032 (18)	0.055 (2)	−0.035 (2)
C18	0.080 (2)	0.082 (2)	0.106 (3)	−0.026 (2)	0.079 (2)	−0.032 (2)
C19	0.0632 (18)	0.0562 (18)	0.0655 (19)	−0.0087 (14)	0.0498 (16)	−0.0096 (14)
C20	0.0415 (13)	0.0274 (12)	0.0391 (13)	−0.0002 (10)	0.0233 (11)	0.0027 (10)
C21	0.0396 (13)	0.0301 (12)	0.0340 (12)	−0.0005 (9)	0.0219 (11)	0.0025 (9)
C22	0.0543 (15)	0.0336 (14)	0.0392 (14)	0.0038 (11)	0.0295 (12)	0.0044 (11)
C23	0.0702 (19)	0.0434 (16)	0.0355 (15)	−0.0025 (13)	0.0256 (14)	−0.0060 (12)
C24	0.0474 (17)	0.0550 (18)	0.0412 (16)	−0.0091 (13)	0.0121 (13)	−0.0018 (13)
C25	0.0417 (15)	0.0582 (18)	0.0542 (18)	−0.0056 (13)	0.0231 (14)	0.0044 (14)
C26	0.0446 (14)	0.0438 (15)	0.0421 (14)	0.0004 (11)	0.0261 (12)	0.0022 (11)
Cd1	0.03456 (11)	0.03147 (11)	0.03994 (12)	0.00079 (7)	0.02394 (9)	0.00196 (7)
N1	0.0367 (10)	0.0370 (11)	0.0375 (11)	0.0005 (8)	0.0240 (9)	0.0023 (9)
N2	0.0336 (10)	0.0365 (11)	0.0373 (11)	0.0004 (8)	0.0228 (9)	0.0009 (8)
O1	0.0432 (10)	0.0568 (12)	0.0545 (11)	0.0086 (8)	0.0316 (9)	0.0137 (9)
O2	0.0457 (10)	0.0594 (12)	0.0537 (11)	0.0101 (9)	0.0367 (9)	0.0135 (9)
O3	0.0634 (13)	0.0808 (16)	0.0761 (15)	0.0276 (11)	0.0457 (12)	0.0327 (13)
O4	0.0434 (10)	0.0479 (11)	0.0676 (13)	−0.0064 (8)	0.0367 (10)	−0.0098 (9)
O5	0.0585 (11)	0.0506 (11)	0.0498 (11)	0.0123 (9)	0.0373 (10)	0.0157 (9)
O6	0.0736 (13)	0.0545 (12)	0.0648 (13)	−0.0001 (10)	0.0532 (11)	−0.0074 (10)

Geometric parameters (Å, º) top

C1—N1	1.331 (3)	C16—H16	0.9300
C1—C2	1.394 (4)	C17—C18	1.373 (5)
C1—H1	0.9300	C17—H17	0.9300
C2—C3	1.353 (4)	C18—C19	1.388 (4)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.407 (4)	C19—H19	0.9300
C3—H3	0.9300	C20—O5ⁱ	1.252 (3)
C4—C12	1.406 (3)	C20—O4	1.260 (3)
C4—C5	1.432 (4)	C20—C21	1.484 (3)
C5—C6	1.335 (5)	C21—C26	1.388 (4)
C5—H5	0.9300	C21—C22	1.399 (3)
C6—C7	1.426 (4)	C22—O6	1.348 (3)
C6—H6	0.9300	C22—C23	1.404 (4)
C7—C11	1.401 (3)	C23—C24	1.370 (4)
C7—C8	1.410 (4)	C23—H23	0.9300
C8—C9	1.358 (4)	C24—C25	1.362 (4)
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.395 (3)	C25—C26	1.378 (4)
C9—H9	0.9300	C25—H25	0.9300
C10—N2	1.331 (3)	C26—H26	0.9300
C10—H10	0.9300	Cd1—O2	2.3271 (16)
C11—N2	1.349 (3)	Cd1—N1	2.355 (2)
C11—C12	1.451 (4)	Cd1—N2	2.3606 (19)
C12—N1	1.355 (3)	Cd1—O4	2.3630 (18)
C13—O1	1.247 (3)	Cd1—O1	2.3993 (19)
C13—O2	1.275 (3)	Cd1—O5	2.4214 (18)
C13—C14	1.480 (3)	Cd1—O5ⁱ	2.4911 (18)
C14—C19	1.388 (4)	O3—H3A	0.8199
C14—C15	1.405 (4)	O5—C20ⁱ	1.252 (3)
C15—O3	1.345 (4)	O5—Cd1ⁱ	2.4911 (18)
C15—C16	1.382 (4)	O6—H6A	0.8200
C16—C17	1.357 (6)

N1—C1—C2	122.8 (3)	O5ⁱ—C20—O4	119.8 (2)
N1—C1—H1	118.6	O5ⁱ—C20—C21	121.0 (2)
C2—C1—H1	118.6	O4—C20—C21	119.2 (2)
C3—C2—C1	119.1 (3)	C26—C21—C22	119.0 (2)
C3—C2—H2	120.4	C26—C21—C20	120.1 (2)
C1—C2—H2	120.4	C22—C21—C20	120.9 (2)
C2—C3—C4	120.4 (3)	O6—C22—C21	122.9 (2)
C2—C3—H3	119.8	O6—C22—C23	118.0 (2)
C4—C3—H3	119.8	C21—C22—C23	119.1 (3)
C12—C4—C3	116.8 (3)	C24—C23—C22	119.8 (3)
C12—C4—C5	119.5 (3)	C24—C23—H23	120.1
C3—C4—C5	123.7 (3)	C22—C23—H23	120.1
C6—C5—C4	121.4 (3)	C25—C24—C23	121.4 (3)
C6—C5—H5	119.3	C25—C24—H24	119.3
C4—C5—H5	119.3	C23—C24—H24	119.3
C5—C6—C7	121.0 (3)	C24—C25—C26	119.6 (3)
C5—C6—H6	119.5	C24—C25—H25	120.2
C7—C6—H6	119.5	C26—C25—H25	120.2
C11—C7—C8	117.0 (2)	C25—C26—C21	121.1 (3)
C11—C7—C6	119.8 (3)	C25—C26—H26	119.5
C8—C7—C6	123.2 (2)	C21—C26—H26	119.5
C9—C8—C7	120.2 (2)	O2—Cd1—N1	106.89 (7)
C9—C8—H8	119.9	O2—Cd1—N2	138.63 (6)
C7—C8—H8	119.9	N1—Cd1—N2	70.68 (7)
C8—C9—C10	118.7 (3)	O2—Cd1—O4	93.20 (6)
C8—C9—H9	120.7	N1—Cd1—O4	158.83 (6)
C10—C9—H9	120.7	N2—Cd1—O4	89.92 (6)
N2—C10—C9	123.1 (2)	O2—Cd1—O1	55.09 (6)
N2—C10—H10	118.4	N1—Cd1—O1	96.97 (7)
C9—C10—H10	118.4	N2—Cd1—O1	83.78 (6)
N2—C11—C7	122.8 (2)	O4—Cd1—O1	88.99 (7)
N2—C11—C12	117.8 (2)	O2—Cd1—O5	88.55 (6)
C7—C11—C12	119.4 (2)	N1—Cd1—O5	78.67 (7)
N1—C12—C4	122.7 (2)	N2—Cd1—O5	128.98 (6)
N1—C12—C11	118.5 (2)	O4—Cd1—O5	109.11 (7)
C4—C12—C11	118.8 (2)	O1—Cd1—O5	140.82 (6)
O1—C13—O2	120.2 (2)	O2—Cd1—O5ⁱ	126.96 (6)
O1—C13—C14	120.7 (2)	N1—Cd1—O5ⁱ	115.33 (6)
O2—C13—C14	119.0 (2)	N2—Cd1—O5ⁱ	86.73 (6)
C19—C14—C15	118.7 (3)	O4—Cd1—O5ⁱ	53.13 (6)
C19—C14—C13	120.3 (2)	O1—Cd1—O5ⁱ	140.94 (6)
C15—C14—C13	120.9 (2)	O5—Cd1—O5ⁱ	70.66 (7)
O3—C15—C16	117.8 (3)	C1—N1—C12	118.2 (2)
O3—C15—C14	122.7 (2)	C1—N1—Cd1	125.56 (17)
C16—C15—C14	119.5 (3)	C12—N1—Cd1	116.05 (15)
C17—C16—C15	120.7 (3)	C10—N2—C11	118.2 (2)
C17—C16—H16	119.6	C10—N2—Cd1	124.98 (16)
C15—C16—H16	119.6	C11—N2—Cd1	116.38 (15)
C16—C17—C18	121.2 (3)	C13—O1—Cd1	91.02 (15)
C16—C17—H17	119.4	C13—O2—Cd1	93.65 (15)
C18—C17—H17	119.4	C15—O3—H3A	109.4
C17—C18—C19	119.0 (3)	C20—O4—Cd1	96.43 (15)
C17—C18—H18	120.5	C20ⁱ—O5—Cd1	163.72 (17)
C19—C18—H18	120.5	C20ⁱ—O5—Cd1ⁱ	90.61 (15)
C14—C19—C18	120.9 (3)	Cd1—O5—Cd1ⁱ	99.62 (6)
C14—C19—H19	119.5	C22—O6—H6A	109.5
C18—C19—H19	119.5

N1—C1—C2—C3	0.8 (5)	O1—Cd1—N1—C1	−99.78 (19)
C1—C2—C3—C4	−0.7 (5)	O5—Cd1—N1—C1	40.75 (19)
C2—C3—C4—C12	0.3 (4)	O5ⁱ—Cd1—N1—C1	102.81 (19)
C2—C3—C4—C5	−178.8 (3)	O2—Cd1—N1—C12	130.28 (16)
C12—C4—C5—C6	0.1 (5)	N2—Cd1—N1—C12	−6.16 (15)
C3—C4—C5—C6	179.1 (3)	O4—Cd1—N1—C12	−30.7 (3)
C4—C5—C6—C7	0.8 (5)	O1—Cd1—N1—C12	74.72 (16)
C5—C6—C7—C11	−0.4 (4)	O5—Cd1—N1—C12	−144.75 (17)
C5—C6—C7—C8	179.9 (3)	O5ⁱ—Cd1—N1—C12	−82.69 (17)
C11—C7—C8—C9	−0.2 (4)	C9—C10—N2—C11	−0.4 (4)
C6—C7—C8—C9	179.4 (3)	C9—C10—N2—Cd1	−172.1 (2)
C7—C8—C9—C10	0.5 (4)	C7—C11—N2—C10	0.7 (3)
C8—C9—C10—N2	−0.2 (4)	C12—C11—N2—C10	−178.6 (2)
C8—C7—C11—N2	−0.4 (4)	C7—C11—N2—Cd1	173.18 (18)
C6—C7—C11—N2	179.9 (2)	C12—C11—N2—Cd1	−6.2 (3)
C8—C7—C11—C12	178.9 (2)	O2—Cd1—N2—C10	84.4 (2)
C6—C7—C11—C12	−0.7 (4)	N1—Cd1—N2—C10	178.3 (2)
C3—C4—C12—N1	0.1 (4)	O4—Cd1—N2—C10	−10.32 (19)
C5—C4—C12—N1	179.3 (2)	O1—Cd1—N2—C10	78.67 (19)
C3—C4—C12—C11	179.7 (2)	O5—Cd1—N2—C10	−125.16 (18)
C5—C4—C12—C11	−1.2 (4)	O5ⁱ—Cd1—N2—C10	−63.38 (18)
N2—C11—C12—N1	0.4 (3)	O2—Cd1—N2—C11	−87.44 (18)
C7—C11—C12—N1	−178.9 (2)	N1—Cd1—N2—C11	6.44 (15)
N2—C11—C12—C4	−179.1 (2)	O4—Cd1—N2—C11	177.81 (16)
C7—C11—C12—C4	1.5 (4)	O1—Cd1—N2—C11	−93.21 (16)
O1—C13—C14—C19	−1.4 (4)	O5—Cd1—N2—C11	62.97 (18)
O2—C13—C14—C19	−179.7 (2)	O5ⁱ—Cd1—N2—C11	124.74 (16)
O1—C13—C14—C15	175.0 (2)	O2—C13—O1—Cd1	1.5 (2)
O2—C13—C14—C15	−3.3 (3)	C14—C13—O1—Cd1	−176.72 (19)
C19—C14—C15—O3	179.4 (3)	O2—Cd1—O1—C13	−0.88 (14)
C13—C14—C15—O3	2.9 (4)	N1—Cd1—O1—C13	104.88 (15)
C19—C14—C15—C16	0.6 (4)	N2—Cd1—O1—C13	174.48 (15)
C13—C14—C15—C16	−175.9 (2)	O4—Cd1—O1—C13	−95.49 (15)
O3—C15—C16—C17	−179.6 (3)	O5—Cd1—O1—C13	24.28 (19)
C14—C15—C16—C17	−0.8 (5)	O5ⁱ—Cd1—O1—C13	−108.56 (16)
C15—C16—C17—C18	0.5 (5)	O1—C13—O2—Cd1	−1.6 (2)
C16—C17—C18—C19	−0.1 (5)	C14—C13—O2—Cd1	176.70 (18)
C15—C14—C19—C18	−0.2 (4)	N1—Cd1—O2—C13	−85.86 (15)
C13—C14—C19—C18	176.3 (2)	N2—Cd1—O2—C13	−6.14 (19)
C17—C18—C19—C14	0.0 (5)	O4—Cd1—O2—C13	87.38 (15)
O5ⁱ—C20—C21—C26	−0.5 (3)	O1—Cd1—O2—C13	0.86 (13)
O4—C20—C21—C26	−179.4 (2)	O5—Cd1—O2—C13	−163.56 (15)
O5ⁱ—C20—C21—C22	179.2 (2)	O5ⁱ—Cd1—O2—C13	132.15 (14)
O4—C20—C21—C22	0.3 (3)	O5ⁱ—C20—O4—Cd1	0.7 (2)
C26—C21—C22—O6	177.6 (2)	C21—C20—O4—Cd1	179.66 (17)
C20—C21—C22—O6	−2.1 (3)	O2—Cd1—O4—C20	134.91 (14)
C26—C21—C22—C23	−1.4 (3)	N1—Cd1—O4—C20	−63.3 (2)
C20—C21—C22—C23	178.9 (2)	N2—Cd1—O4—C20	−86.37 (15)
O6—C22—C23—C24	−178.3 (2)	O1—Cd1—O4—C20	−170.14 (15)
C21—C22—C23—C24	0.8 (4)	O5—Cd1—O4—C20	45.33 (15)
C22—C23—C24—C25	0.4 (4)	O5ⁱ—Cd1—O4—C20	−0.40 (13)
C23—C24—C25—C26	−1.1 (4)	O2—Cd1—O5—C20ⁱ	−34.5 (6)
C24—C25—C26—C21	0.4 (4)	N1—Cd1—O5—C20ⁱ	−142.0 (6)
C22—C21—C26—C25	0.8 (4)	N2—Cd1—O5—C20ⁱ	164.6 (6)
C20—C21—C26—C25	−179.5 (2)	O4—Cd1—O5—C20ⁱ	58.4 (6)
C2—C1—N1—C12	−0.4 (4)	O1—Cd1—O5—C20ⁱ	−54.9 (6)
C2—C1—N1—Cd1	174.0 (2)	O5ⁱ—Cd1—O5—C20ⁱ	95.8 (6)
C4—C12—N1—C1	−0.1 (4)	O2—Cd1—O5—Cd1ⁱ	−162.70 (7)
C11—C12—N1—C1	−179.6 (2)	N1—Cd1—O5—Cd1ⁱ	89.75 (7)
C4—C12—N1—Cd1	−174.99 (19)	N2—Cd1—O5—Cd1ⁱ	36.35 (10)
C11—C12—N1—Cd1	5.5 (3)	O4—Cd1—O5—Cd1ⁱ	−69.82 (8)
O2—Cd1—N1—C1	−44.2 (2)	O1—Cd1—O5—Cd1ⁱ	176.89 (7)
N2—Cd1—N1—C1	179.3 (2)	O5ⁱ—Cd1—O5—Cd1ⁱ	−32.44 (8)
O4—Cd1—N1—C1	154.77 (19)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O4	0.82	1.86	2.579 (3)	146
O3—H3A···O2	0.82	1.87	2.576 (2)	143

Experimental details

Crystal data
Chemical formula	[Cd₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂]
M_r	1133.65
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	27.9391 (19), 10.3078 (7), 20.468 (2)
β (°)	130.770 (1)
V (Å³)	4464.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.30 × 0.25 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.748, 0.837
No. of measured, independent and observed [I > 2σ(I)] reflections	11963, 4390, 3671
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.067, 1.06
No. of reflections	4390
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.36

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O4	0.82	1.86	2.579 (3)	145.7
O3—H3A···O2	0.82	1.87	2.576 (2)	143.2

Acknowledgements

The authors gratefully acknowledge financial support from the Scientific Research Project for Comprehensive Talent Cultivation of South China Normal University (2008–2009).

References

Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Du, M., Li, C. P., Zhao, X. J. & Yu, Q. (2007). CrystEngComm, 9, 1011–1028. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Horike, S., Tanaka, D., Nakagawa, K. & Kitagawa, S. (2007). Chem. Commun. pp. 3395–3397. Web of Science CSD CrossRef Google Scholar
Humphrey, S. M., Chang, J. S., Jhung, S. H., Yoon, J. W. & Wood, P. T. (2007). Angew. Chem. Int. Ed. 46, 272–275. Web of Science CSD CrossRef CAS Google Scholar
Pan, T.-T., Su, J.-R. & Xu, D.-J. (2006). Acta Cryst. E62, m2183–m2185. 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
Sudik, A. C., Millward, A. R., Ockwig, N. W., Cote, A. P., Kim, J. & Yaghi, O. M. (2005). J. Am. Chem. Soc. 127, 7110–7118. Web of Science CSD CrossRef PubMed CAS Google Scholar
Tomas, A., Retailleau, P., Viossat, B., Prange, T. & Lemoine, P. (2006). Z. Kristallogr. New Cryst. Struct. 221, 517–519. CAS Google Scholar
Tong, M. L., Lee, H. K., Chen, X. M., Huang, R. B. & Mak, T. C. W. (1999). J. Chem. Soc. Dalton Trans. pp. 3657–3659. Web of Science CSD CrossRef Google Scholar
Zhang, K. L., Gao, H. Y., Qiao, N., Zhou, F. & Diao, G. W. (2008). Inorg. Chim. Acta, 361, 153–160. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.