Bis{μ-2-[3-carboxyl­atometh­yl-4-(phenyl­sulfan­yl)phen­yl]propano­ato-κ4O,O′:O′′,O′′′}bis­[(2,2′-bipyridine-κ2N,N′)cadmium]

Li, L.; Ding, Y.-Q.; Diao, K.-S.

doi:10.1107/S1600536812013049

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page m511

doi:10.1107/S1600536812013049

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Bis{μ-2-[3-carboxylatomethyl-4-(phenylsulfanyl)phenyl]propanoato-κ⁴O,O′:O′′,O′′′}bis[(2,2′-bipyridine-κ²N,N′)cadmium]

Long Li,^a Yu-Qiu Ding ^a and Kai-Sheng Diao ^a ^*

^aSchool of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, People's Republic of China
^*Correspondence e-mail: 497426630@qq.com

(Received 11 March 2012; accepted 25 March 2012; online 31 March 2012)

In the title complex, [Cd₂(C₁₇H₁₄O₄S)₂(C₁₀H₈N₂)₂], which was hydrothermally synthesized, the Cd^II cation is hexacoordinated in a distorted octahedral geometry by two N atoms from a 2,2′-bipyridine ligand and by four O atoms from two different 2-[3-carboxylatomethyl-4-(phenylsulfanyl)phenyl]propanoate ligands, forming a cyclic dimetallic complex.

Related literature

For reviews of metal-organic network solids, see: Batten & Robson (1998 ); Lu (2003 ); Moulton & Zaworotko (2001 ); Pan et al. (2004 ). For the synthesis and structure of helical Cd complexes with related ligands, see: Wang et al. (2004 ).

Experimental

Crystal data

[Cd₂(C₁₇H₁₄O₄S)₂(C₁₀H₈N₂)₂]
M_r = 1165.85
Monoclinic, P 2₁ /c
a = 13.567 (3) Å
b = 11.572 (3) Å
c = 15.595 (4) Å
β = 92.540 (3)°
V = 2446.2 (10) Å³
Z = 2
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 296 K
0.35 × 0.34 × 0.32 mm

Data collection

Bruker SMART BREEZE CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.718, T_max = 0.737
14971 measured reflections
5706 independent reflections
4170 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.090
S = 1.04
5706 reflections
329 parameters
3 restraints
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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: 10.1107/S1600536812013049/mw2060sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013049/mw2060Isup2.hkl

checkCIF report

Comment top

The design and synthesis of coordination polymers is of great interest due to their intriguing topologic architecture and significant application in many fields (Pan et al., 2004; Batten et al., 1998). Among the variety of organic molecules acting as linkers in the design of supramolecular networks, heterocyclic N rings and polycarboxylates are the most widely used ligands due to their rigidity in structure and flexibility in coordination modes (Moulton et al., 2001; Wang et al., 2004; Lu et al., 2003). In this work we report a cyclic Cd^II coordination complex, (I), constructed from 5-(1-carboxyethyl)-2-(phenylthio)phenylacetic acid and 2,2'-bipyridine (Fig. 1). The O—Cd bond distances range from 2.277 (6) to 2.416 (6) Å and the Cd—N bond distances are 2.311 (3) and 2.320 (3) Å. The dihedral angle between two benzene rings in the same L ligand is 78.73 (6)° and the C—S—C angle is 102.11 (6)°. It is to be noted that both carboxylates of L are bidentate but asymmetrically coordinated with the Cd1—O1 and Cd1—O2 bond distance of 2.276 (3) and 2.415 (3) Å, respectively while the Cd1—O3 and Cd1—O4 distances are 2.345 (3) and 2.309 (3) Å. These differences can likely be attibuted to packing considerations since of the four carboxylate oxygen atoms, only O1 is not involved with C—H···O hydrogen bonding interactions. The self-assembly of the metal with 5-(1-carboxyethyl)-2-(phenylthio)phenylacetic acid and 2,2'-bipyridine links the Cd ions into a cyclic dimer (Fig. 1). Weak π-π stacking interactions between pyridine rings from different bipy ligands (interplanar spacing = 3.708 (4) Å, dihedral angle between planes = 1.07 (4)°) as well as a number of short (C—H···X (X = O, N)) contacts generate a 3-D structure (Fig. 2).

Related literature top

For reviews of metal-organic network solids, see: Batten & Robson (1998); Lu (2003); Moulton & Zaworotko (2001); Pan et al. (2004). For the synthesis and structure of helical Cd complexes with related ligands, see: Wang et al. (2004).

Experimental top

H₂L (0.5 mmol) and 2,2'-bipyridine (0.5 mmol) were dissolved in a mixture of 5 ml of ethanol and 15 ml of H₂O to which an aqueous solution of sodium hydroxide was added dropwise with stirring to adjust the pH to 6. After addition of 10 ml of an aqueous solution of cadmium chloride (0.5 mmol) the mixture was heated at 403 K for 3 days. After cooling to room temperature, the reaction solution was filtered to remove a small quantity of white precipitate. Slow evaporation of the filtrate at room temperature over three days produced X-ray quality colorless block-shaped single crystals.

Structure description top

For reviews of metal-organic network solids, see: Batten & Robson (1998); Lu (2003); Moulton & Zaworotko (2001); Pan et al. (2004). For the synthesis and structure of helical Cd complexes with related ligands, see: Wang et al. (2004).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The molecular packing diagram for the crystal of (I).

Bis{µ-2-[3-carboxylatomethyl-4-(phenylsulfanyl)phenyl]propanoato- κ⁴O,O':O'',O'''}bis[(2,2'-bipyridine- κ²N,N')cadmium] top

Crystal data top

[Cd₂(C₁₇H₁₄O₄S)₂(C₁₀H₈N₂)₂]	F(000) = 1176
M_r = 1165.85	D_x = 1.583 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6794 reflections
a = 13.567 (3) Å	θ = 2.3–27.8°
b = 11.572 (3) Å	µ = 1.02 mm⁻¹
c = 15.595 (4) Å	T = 296 K
β = 92.540 (3)°	Block, colorless
V = 2446.2 (10) Å³	0.35 × 0.34 × 0.32 mm
Z = 2

Data collection top

Bruker SMART BREEZE CCD area-detector diffractometer	5706 independent reflections
Radiation source: fine-focus sealed tube	4170 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
phi and ω scans	θ_max = 28.2°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→18
T_min = 0.718, T_max = 0.737	k = −9→15
14971 measured reflections	l = −20→20

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0222P)² + 1.2239P] where P = (F_o² + 2F_c²)/3
5706 reflections	(Δ/σ)_max = 0.002
329 parameters	Δρ_max = 0.59 e Å⁻³
3 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Cd₂(C₁₇H₁₄O₄S)₂(C₁₀H₈N₂)₂]	V = 2446.2 (10) Å³
M_r = 1165.85	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.567 (3) Å	µ = 1.02 mm⁻¹
b = 11.572 (3) Å	T = 296 K
c = 15.595 (4) Å	0.35 × 0.34 × 0.32 mm
β = 92.540 (3)°

Data collection top

Bruker SMART BREEZE CCD area-detector diffractometer	5706 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4170 reflections with I > 2σ(I)
T_min = 0.718, T_max = 0.737	R_int = 0.042
14971 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	3 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.04	Δρ_max = 0.59 e Å⁻³
5706 reflections	Δρ_min = −0.67 e Å⁻³
329 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
Cd1	−0.076611 (16)	0.93279 (2)	0.764046 (13)	0.04782 (9)
S1	0.27579 (6)	0.85650 (8)	0.73380 (5)	0.0515 (2)
N1	−0.00382 (18)	0.8216 (2)	0.87232 (14)	0.0398 (6)
N2	−0.14700 (19)	0.9786 (3)	0.89259 (15)	0.0453 (6)
O1	−0.17570 (19)	0.8271 (2)	0.67240 (15)	0.0656 (7)
O2	−0.22891 (18)	1.0016 (3)	0.69612 (15)	0.0637 (7)
O3	0.06431 (16)	0.9391 (2)	0.68258 (14)	0.0507 (6)
O4	0.03442 (16)	1.0841 (2)	0.76726 (15)	0.0525 (6)
C1	0.0686 (2)	0.7475 (3)	0.8589 (2)	0.0514 (8)
H1	0.0923	0.7415	0.8040	0.062*
C2	0.1096 (3)	0.6798 (3)	0.9225 (3)	0.0648 (10)
H2	0.1604	0.6288	0.9113	0.078*
C3	0.0746 (3)	0.6885 (4)	1.0030 (3)	0.0728 (12)
H3	0.1007	0.6422	1.0472	0.087*
C4	0.0007 (3)	0.7660 (3)	1.0185 (2)	0.0603 (10)
H4	−0.0235	0.7731	1.0731	0.072*
C5	−0.0371 (2)	0.8332 (3)	0.95146 (17)	0.0397 (7)
C6	−0.1152 (2)	0.9199 (3)	0.96275 (17)	0.0403 (7)
C7	−0.1544 (3)	0.9423 (3)	1.0416 (2)	0.0593 (10)
H7	−0.1325	0.9013	1.0900	0.071*
C8	−0.2256 (3)	1.0254 (4)	1.0475 (2)	0.0762 (12)
H8	−0.2527	1.0412	1.1000	0.091*
C9	−0.2563 (3)	1.0845 (4)	0.9761 (3)	0.0728 (11)
H9	−0.3044	1.1414	0.9790	0.087*
C10	−0.2157 (3)	1.0593 (3)	0.9002 (3)	0.0611 (9)
H10	−0.2369	1.1003	0.8515	0.073*
C11	−0.2382 (2)	0.9068 (4)	0.66121 (19)	0.0512 (9)
C12	0.0872 (2)	1.0346 (3)	0.71384 (18)	0.0399 (7)
C13	0.1804 (2)	1.0957 (3)	0.6894 (2)	0.0527 (8)
H13A	0.1622	1.1721	0.6684	0.063*
H13B	0.2218	1.1062	0.7411	0.063*
C14	0.2415 (2)	1.0395 (3)	0.62373 (19)	0.0390 (7)
C15	0.2532 (2)	1.0938 (3)	0.5439 (2)	0.0483 (8)
H15	0.2175	1.1608	0.5313	0.058*
C16	0.3151 (2)	1.0519 (3)	0.48389 (18)	0.0496 (9)
C17	0.3342 (3)	1.1070 (4)	0.3955 (2)	0.0409 (10)	0.770 (6)
H17	0.3875	1.0645	0.3690	0.049*	0.770 (6)
C18	0.3637 (5)	1.2319 (5)	0.4048 (4)	0.0575 (15)	0.770 (6)
H18A	0.3749	1.2635	0.3492	0.086*	0.770 (6)
H18B	0.3118	1.2742	0.4306	0.086*	0.770 (6)
H18C	0.4231	1.2377	0.4404	0.086*	0.770 (6)
C17A	0.2979 (9)	1.1532 (9)	0.4175 (6)	0.0409 (10)	0.230 (6)
H17A	0.2655	1.2209	0.4413	0.049*	0.230 (6)
C18A	0.3971 (12)	1.176 (3)	0.3811 (13)	0.079 (8)	0.230 (6)
H18D	0.3915	1.2402	0.3425	0.119*	0.230 (6)
H18E	0.4437	1.1937	0.4273	0.119*	0.230 (6)
H18F	0.4193	1.1091	0.3508	0.119*	0.230 (6)
C19	0.3657 (2)	0.9531 (3)	0.50239 (19)	0.0538 (9)
H19	0.4095	0.9246	0.4633	0.065*
C20	0.3535 (2)	0.8944 (3)	0.57788 (19)	0.0470 (7)
H20	0.3869	0.8252	0.5882	0.056*
C21	0.2919 (2)	0.9377 (3)	0.63872 (17)	0.0351 (6)
C22	0.3985 (2)	0.8454 (3)	0.77750 (18)	0.0465 (8)
C23	0.4312 (3)	0.7405 (3)	0.8089 (2)	0.0577 (9)
H23	0.3905	0.6758	0.8044	0.069*
C24	0.5250 (3)	0.7317 (5)	0.8472 (3)	0.0826 (14)
H24	0.5469	0.6608	0.8687	0.099*
C25	0.5852 (3)	0.8251 (5)	0.8536 (3)	0.0920 (16)
H25	0.6480	0.8182	0.8797	0.110*
C26	0.5534 (4)	0.9301 (4)	0.8216 (3)	0.0930 (17)
H26	0.5951	0.9939	0.8249	0.112*
C27	0.4590 (3)	0.9406 (4)	0.7844 (3)	0.0704 (12)
H27	0.4367	1.0120	0.7642	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.04260 (13)	0.07524 (19)	0.02515 (11)	−0.00810 (12)	−0.00395 (8)	0.00632 (10)
S1	0.0472 (4)	0.0652 (6)	0.0417 (4)	−0.0015 (4)	−0.0019 (3)	0.0187 (4)
N1	0.0453 (14)	0.0434 (15)	0.0302 (11)	−0.0060 (12)	−0.0031 (10)	−0.0014 (11)
N2	0.0453 (14)	0.0576 (17)	0.0327 (12)	−0.0001 (13)	−0.0010 (10)	0.0031 (12)
O1	0.0723 (17)	0.0725 (19)	0.0504 (13)	−0.0072 (15)	−0.0146 (12)	−0.0019 (13)
O2	0.0636 (16)	0.075 (2)	0.0510 (14)	−0.0048 (14)	−0.0140 (11)	0.0087 (14)
O3	0.0473 (12)	0.0600 (16)	0.0452 (12)	−0.0121 (11)	0.0076 (9)	−0.0100 (11)
O4	0.0461 (12)	0.0600 (16)	0.0519 (13)	0.0043 (11)	0.0093 (10)	−0.0064 (11)
C1	0.056 (2)	0.050 (2)	0.0483 (18)	−0.0058 (16)	0.0004 (15)	−0.0073 (15)
C2	0.062 (2)	0.057 (2)	0.075 (2)	0.0122 (19)	−0.0037 (19)	0.002 (2)
C3	0.078 (3)	0.076 (3)	0.064 (2)	0.009 (2)	−0.010 (2)	0.024 (2)
C4	0.067 (2)	0.079 (3)	0.0349 (16)	−0.001 (2)	−0.0035 (15)	0.0194 (17)
C5	0.0426 (16)	0.0471 (19)	0.0288 (13)	−0.0122 (14)	−0.0056 (11)	0.0016 (12)
C6	0.0414 (15)	0.052 (2)	0.0269 (13)	−0.0128 (14)	−0.0025 (11)	−0.0012 (12)
C7	0.073 (2)	0.073 (3)	0.0320 (15)	0.001 (2)	0.0021 (15)	−0.0047 (16)
C8	0.090 (3)	0.091 (3)	0.048 (2)	0.007 (3)	0.014 (2)	−0.025 (2)
C9	0.077 (3)	0.063 (3)	0.078 (3)	0.012 (2)	0.008 (2)	−0.015 (2)
C10	0.059 (2)	0.062 (3)	0.061 (2)	0.0068 (19)	0.0008 (17)	0.0065 (18)
C11	0.0492 (19)	0.074 (3)	0.0293 (14)	−0.0195 (18)	−0.0064 (13)	0.0211 (16)
C12	0.0363 (15)	0.0480 (19)	0.0350 (14)	0.0045 (13)	−0.0029 (12)	0.0031 (13)
C13	0.0452 (18)	0.046 (2)	0.067 (2)	0.0012 (15)	0.0081 (15)	−0.0095 (16)
C14	0.0284 (13)	0.0426 (18)	0.0454 (16)	−0.0034 (12)	−0.0034 (11)	−0.0021 (13)
C15	0.0338 (15)	0.049 (2)	0.061 (2)	−0.0029 (14)	−0.0176 (14)	0.0174 (16)
C16	0.0398 (16)	0.076 (3)	0.0318 (14)	−0.0213 (17)	−0.0106 (12)	0.0094 (15)
C17	0.031 (2)	0.062 (3)	0.0298 (18)	−0.0041 (19)	0.0038 (14)	0.0031 (18)
C18	0.063 (4)	0.063 (4)	0.046 (3)	−0.020 (3)	−0.003 (2)	0.005 (3)
C17A	0.031 (2)	0.062 (3)	0.0298 (18)	−0.0041 (19)	0.0038 (14)	0.0031 (18)
C18A	0.062 (13)	0.13 (2)	0.050 (12)	−0.021 (14)	−0.007 (9)	0.024 (13)
C19	0.0526 (19)	0.078 (3)	0.0308 (15)	−0.0067 (18)	0.0055 (13)	−0.0073 (16)
C20	0.0495 (18)	0.050 (2)	0.0414 (16)	0.0077 (15)	0.0030 (13)	−0.0021 (15)
C21	0.0359 (14)	0.0401 (17)	0.0290 (13)	0.0008 (13)	−0.0033 (10)	0.0023 (12)
C22	0.0513 (18)	0.057 (2)	0.0312 (14)	0.0008 (16)	−0.0028 (12)	0.0070 (14)
C23	0.062 (2)	0.056 (2)	0.054 (2)	0.0041 (18)	−0.0080 (16)	0.0128 (17)
C24	0.071 (3)	0.102 (4)	0.074 (3)	0.016 (3)	−0.010 (2)	0.037 (3)
C25	0.065 (3)	0.130 (5)	0.078 (3)	−0.007 (3)	−0.027 (2)	0.035 (3)
C26	0.085 (3)	0.105 (4)	0.086 (3)	−0.039 (3)	−0.037 (3)	0.033 (3)
C27	0.076 (3)	0.066 (3)	0.067 (2)	−0.010 (2)	−0.022 (2)	0.023 (2)

Geometric parameters (Å, º) top

Cd1—O1	2.275 (2)	C13—H13A	0.9700
Cd1—O4	2.309 (2)	C13—H13B	0.9700
Cd1—N1	2.310 (2)	C14—C21	1.377 (4)
Cd1—N2	2.320 (3)	C14—C15	1.411 (4)
Cd1—O3	2.343 (2)	C15—C16	1.373 (5)
Cd1—O2	2.415 (2)	C15—H15	0.9300
S1—C22	1.776 (3)	C16—C19	1.359 (5)
S1—C21	1.777 (3)	C16—C17	1.551 (5)
N1—C1	1.328 (4)	C16—C17A	1.574 (9)
N1—C5	1.340 (4)	C17—C18	1.505 (6)
N2—C10	1.329 (4)	C17—C11ⁱ	1.550 (4)
N2—C6	1.342 (4)	C17—H17	0.9800
O1—C11	1.260 (4)	C18—H18A	0.9600
O2—C11	1.228 (4)	C18—H18B	0.9600
O3—C12	1.242 (4)	C18—H18C	0.9601
O4—C12	1.260 (4)	C17A—C18A	1.506 (10)
C1—C2	1.364 (5)	C17A—C11ⁱ	1.599 (9)
C1—H1	0.9300	C17A—H17A	0.9800
C2—C3	1.365 (5)	C18A—H18D	0.9600
C2—H2	0.9300	C18A—H18E	0.9600
C3—C4	1.375 (6)	C18A—H18F	0.9600
C3—H3	0.9300	C19—C20	1.375 (5)
C4—C5	1.384 (4)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.386 (4)
C5—C6	1.475 (4)	C20—H20	0.9300
C6—C7	1.385 (4)	C22—C23	1.375 (5)
C7—C8	1.369 (6)	C22—C27	1.376 (5)
C7—H7	0.9300	C23—C24	1.385 (5)
C8—C9	1.356 (6)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.357 (7)
C9—C10	1.359 (6)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.377 (6)
C10—H10	0.9300	C25—H25	0.9300
C11—C17ⁱ	1.550 (4)	C26—C27	1.387 (6)
C11—C17Aⁱ	1.599 (9)	C26—H26	0.9300
C12—C13	1.513 (4)	C27—H27	0.9300
C13—C14	1.494 (4)

O1—Cd1—O4	142.02 (9)	C12—C13—H13A	107.9
O1—Cd1—N1	112.41 (9)	C14—C13—H13B	107.9
O4—Cd1—N1	98.58 (8)	C12—C13—H13B	107.9
O1—Cd1—N2	114.29 (10)	H13A—C13—H13B	107.2
O4—Cd1—N2	95.81 (9)	C21—C14—C15	117.2 (3)
N1—Cd1—N2	71.01 (9)	C21—C14—C13	122.9 (3)
O1—Cd1—O3	98.61 (9)	C15—C14—C13	119.9 (3)
O4—Cd1—O3	56.01 (8)	C16—C15—C14	122.7 (3)
N1—Cd1—O3	94.65 (9)	C16—C15—H15	118.7
N2—Cd1—O3	146.99 (8)	C14—C15—H15	118.7
O1—Cd1—O2	55.34 (10)	C19—C16—C15	118.2 (3)
O4—Cd1—O2	107.72 (9)	C19—C16—C17	115.6 (3)
N1—Cd1—O2	146.53 (9)	C15—C16—C17	126.3 (3)
N2—Cd1—O2	85.80 (9)	C19—C16—C17A	145.6 (6)
O3—Cd1—O2	117.05 (8)	C15—C16—C17A	96.2 (6)
C22—S1—C21	102.15 (14)	C18—C17—C11ⁱ	111.5 (4)
C1—N1—C5	119.5 (3)	C18—C17—C16	111.3 (4)
C1—N1—Cd1	122.7 (2)	C11ⁱ—C17—C16	107.2 (3)
C5—N1—Cd1	117.8 (2)	C18—C17—H17	109.0
C10—N2—C6	118.9 (3)	C11ⁱ—C17—H17	108.9
C10—N2—Cd1	123.7 (2)	C16—C17—H17	108.9
C6—N2—Cd1	117.3 (2)	C17—C18—H18A	109.3
C11—O1—Cd1	93.9 (2)	C17—C18—H18B	109.5
C11—O2—Cd1	88.2 (2)	H18A—C18—H18B	109.5
C12—O3—Cd1	90.61 (18)	C17—C18—H18C	109.6
C12—O4—Cd1	91.7 (2)	H18A—C18—H18C	109.5
N1—C1—C2	122.4 (3)	H18B—C18—H18C	109.5
N1—C1—H1	118.8	C18A—C17A—C16	105.6 (13)
C2—C1—H1	118.8	C18A—C17A—C11ⁱ	102.5 (12)
C1—C2—C3	118.7 (4)	C16—C17A—C11ⁱ	103.7 (6)
C1—C2—H2	120.6	C18A—C17A—H17A	115.3
C3—C2—H2	120.6	C16—C17A—H17A	113.8
C2—C3—C4	119.6 (3)	C11ⁱ—C17A—H17A	114.6
C2—C3—H3	120.2	C17A—C18A—H18E	108.9
C4—C3—H3	120.2	H18D—C18A—H18E	109.5
C3—C4—C5	119.0 (3)	C17A—C18A—H18F	110.6
C3—C4—H4	120.5	H18D—C18A—H18F	109.5
C5—C4—H4	120.5	H18E—C18A—H18F	109.5
N1—C5—C4	120.7 (3)	C16—C19—C20	121.2 (3)
N1—C5—C6	116.9 (2)	C16—C19—H19	119.4
C4—C5—C6	122.5 (3)	C20—C19—H19	119.4
N2—C6—C7	120.5 (3)	C19—C20—C21	120.5 (3)
N2—C6—C5	116.9 (3)	C19—C20—H20	119.8
C7—C6—C5	122.6 (3)	C21—C20—H20	119.8
C8—C7—C6	119.4 (3)	C14—C21—C20	120.2 (3)
C8—C7—H7	120.3	C14—C21—S1	121.0 (2)
C6—C7—H7	120.3	C20—C21—S1	118.7 (2)
C9—C8—C7	119.4 (4)	C23—C22—C27	119.8 (3)
C9—C8—H8	120.3	C23—C22—S1	118.9 (3)
C7—C8—H8	120.3	C27—C22—S1	121.2 (3)
C8—C9—C10	119.0 (4)	C22—C23—C24	119.6 (4)
C8—C9—H9	120.5	C22—C23—H23	120.2
C10—C9—H9	120.5	C24—C23—H23	120.2
N2—C10—C9	122.8 (4)	C25—C24—C23	120.9 (4)
N2—C10—H10	118.6	C25—C24—H24	119.6
C9—C10—H10	118.6	C23—C24—H24	119.6
O2—C11—O1	122.5 (3)	C24—C25—C26	119.9 (4)
O2—C11—C17ⁱ	114.4 (4)	C24—C25—H25	120.1
O1—C11—C17ⁱ	123.1 (4)	C26—C25—H25	120.1
O2—C11—C17Aⁱ	140.1 (5)	C25—C26—C27	119.9 (4)
O1—C11—C17Aⁱ	95.9 (5)	C25—C26—H26	120.1
O3—C12—O4	121.6 (3)	C27—C26—H26	120.1
O3—C12—C13	121.0 (3)	C22—C27—C26	120.0 (4)
O4—C12—C13	117.4 (3)	C22—C27—H27	120.0
C14—C13—C12	117.7 (3)	C26—C27—H27	120.0
C14—C13—H13A	107.9

O1—Cd1—N1—C1	72.7 (3)	C5—C6—C7—C8	178.9 (3)
O4—Cd1—N1—C1	−84.9 (2)	C6—C7—C8—C9	−0.2 (6)
N2—Cd1—N1—C1	−178.1 (3)	C7—C8—C9—C10	0.2 (7)
O3—Cd1—N1—C1	−28.6 (2)	C6—N2—C10—C9	−0.8 (6)
O2—Cd1—N1—C1	133.3 (2)	Cd1—N2—C10—C9	179.7 (3)
O1—Cd1—N1—C5	−107.1 (2)	C8—C9—C10—N2	0.2 (7)
O4—Cd1—N1—C5	95.3 (2)	Cd1—O2—C11—O1	−0.5 (3)
N2—Cd1—N1—C5	2.0 (2)	Cd1—O2—C11—C17ⁱ	178.0 (2)
O3—Cd1—N1—C5	151.6 (2)	Cd1—O2—C11—C17Aⁱ	−162.3 (8)
O2—Cd1—N1—C5	−46.6 (3)	Cd1—O1—C11—O2	0.5 (3)
O1—Cd1—N2—C10	−75.4 (3)	Cd1—O1—C11—C17ⁱ	−177.9 (3)
O4—Cd1—N2—C10	80.8 (3)	Cd1—O1—C11—C17Aⁱ	168.9 (4)
N1—Cd1—N2—C10	177.9 (3)	Cd1—O3—C12—O4	−0.9 (3)
O3—Cd1—N2—C10	109.8 (3)	Cd1—O3—C12—C13	178.7 (3)
O2—Cd1—N2—C10	−26.6 (3)	Cd1—O4—C12—O3	0.9 (3)
O1—Cd1—N2—C6	105.1 (2)	Cd1—O4—C12—C13	−178.7 (2)
O4—Cd1—N2—C6	−98.7 (2)	O3—C12—C13—C14	2.5 (5)
N1—Cd1—N2—C6	−1.6 (2)	O4—C12—C13—C14	−177.9 (3)
O3—Cd1—N2—C6	−69.7 (3)	C12—C13—C14—C21	−67.9 (4)
O2—Cd1—N2—C6	153.9 (2)	C12—C13—C14—C15	115.3 (3)
O4—Cd1—O1—C11	−73.7 (2)	C21—C14—C15—C16	−2.9 (4)
N1—Cd1—O1—C11	144.02 (19)	C13—C14—C15—C16	174.2 (3)
N2—Cd1—O1—C11	65.6 (2)	C14—C15—C16—C19	0.9 (5)
O3—Cd1—O1—C11	−117.3 (2)	C14—C15—C16—C17	−178.6 (3)
O2—Cd1—O1—C11	−0.26 (18)	C14—C15—C16—C17A	−176.7 (4)
O1—Cd1—O2—C11	0.27 (18)	C19—C16—C17—C18	−126.6 (4)
O4—Cd1—O2—C11	141.99 (19)	C15—C16—C17—C18	53.0 (5)
N1—Cd1—O2—C11	−77.9 (2)	C17A—C16—C17—C18	49.1 (8)
N2—Cd1—O2—C11	−123.2 (2)	C19—C16—C17—C11ⁱ	111.2 (4)
O3—Cd1—O2—C11	81.7 (2)	C15—C16—C17—C11ⁱ	−69.2 (5)
O1—Cd1—O3—C12	149.75 (18)	C17A—C16—C17—C11ⁱ	−73.1 (7)
O4—Cd1—O3—C12	0.51 (16)	C19—C16—C17A—C18A	−34.7 (15)
N1—Cd1—O3—C12	−96.72 (18)	C15—C16—C17A—C18A	141.6 (12)
N2—Cd1—O3—C12	−35.0 (3)	C17—C16—C17A—C18A	−41.6 (13)
O2—Cd1—O3—C12	94.40 (18)	C19—C16—C17A—C11ⁱ	72.7 (10)
O1—Cd1—O4—C12	−55.7 (2)	C15—C16—C17A—C11ⁱ	−111.0 (6)
N1—Cd1—O4—C12	89.33 (18)	C17—C16—C17A—C11ⁱ	65.8 (6)
N2—Cd1—O4—C12	160.94 (18)	C15—C16—C19—C20	1.9 (5)
O3—Cd1—O4—C12	−0.50 (16)	C17—C16—C19—C20	−178.5 (3)
O2—Cd1—O4—C12	−111.62 (18)	C17A—C16—C19—C20	177.7 (7)
C5—N1—C1—C2	1.6 (5)	C16—C19—C20—C21	−2.7 (5)
Cd1—N1—C1—C2	−178.2 (3)	C15—C14—C21—C20	2.0 (4)
N1—C1—C2—C3	0.1 (6)	C13—C14—C21—C20	−174.9 (3)
C1—C2—C3—C4	−1.1 (6)	C15—C14—C21—S1	−175.4 (2)
C2—C3—C4—C5	0.4 (6)	C13—C14—C21—S1	7.6 (4)
C1—N1—C5—C4	−2.4 (4)	C19—C20—C21—C14	0.6 (5)
Cd1—N1—C5—C4	177.5 (2)	C19—C20—C21—S1	178.1 (2)
C1—N1—C5—C6	177.9 (3)	C22—S1—C21—C14	−124.0 (2)
Cd1—N1—C5—C6	−2.3 (3)	C22—S1—C21—C20	58.5 (3)
C3—C4—C5—N1	1.4 (5)	C21—S1—C22—C23	−135.7 (3)
C3—C4—C5—C6	−178.9 (3)	C21—S1—C22—C27	47.8 (3)
C10—N2—C6—C7	0.8 (5)	C27—C22—C23—C24	−0.1 (6)
Cd1—N2—C6—C7	−179.6 (2)	S1—C22—C23—C24	−176.7 (3)
C10—N2—C6—C5	−178.5 (3)	C22—C23—C24—C25	−0.4 (7)
Cd1—N2—C6—C5	1.0 (3)	C23—C24—C25—C26	−0.2 (8)
N1—C5—C6—N2	0.8 (4)	C24—C25—C26—C27	1.3 (8)
C4—C5—C6—N2	−179.0 (3)	C23—C22—C27—C26	1.2 (6)
N1—C5—C6—C7	−178.5 (3)	S1—C22—C27—C26	177.7 (4)
C4—C5—C6—C7	1.7 (5)	C25—C26—C27—C22	−1.8 (8)
N2—C6—C7—C8	−0.4 (5)

Symmetry code: (i) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cd₂(C₁₇H₁₄O₄S)₂(C₁₀H₈N₂)₂]
M_r	1165.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.567 (3), 11.572 (3), 15.595 (4)
β (°)	92.540 (3)
V (Å³)	2446.2 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.35 × 0.34 × 0.32

Data collection
Diffractometer	Bruker SMART BREEZE CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.718, 0.737
No. of measured, independent and observed [I > 2σ(I)] reflections	14971, 5706, 4170
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.665

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.090, 1.04
No. of reflections	5706
No. of parameters	329
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.67

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported financially by the Scientific Research Program of the Education Department of Guangxi Zhuang Autonomous Region (project No. 201010LX081) and the Scientific Research Program of Guangxi University for Nationalities (project No. 2010QD019).

References

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