catena-Poly[[(2-amino-1,3-benzothia­zole-6-carboxyl­ato-κ2O,O′)(2,2′-bipyridyl-κ2N,N′)cadmium]-μ-2-amino-1,3-benzothia­zole-6-carboxyl­ato-κ3N1:O,O′]

Gao, D.; Fang, X.; Zhang, K.-K.; Cai, L.-M.; Wang, J.-D.

doi:10.1107/S160053681201642X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m641-m642

doi:10.1107/S160053681201642X

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catena-Poly[[(2-amino-1,3-benzothiazole-6-carboxylato-κ²O,O′)(2,2′-bipyridyl-κ²N,N′)cadmium]-μ-2-amino-1,3-benzothiazole-6-carboxylato-κ³N¹:O,O′]

Dan Gao,^a Xin Fang,^a ^* Ke-Ke Zhang,^a Li-Mao Cai ^a and Jun-Dong Wang ^a

^aDepartment of Chemistry, University of Fuzhou, Fuzhou350108, People's Republic of China
^*Correspondence e-mail: fangxin@fzu.edu.cn

(Received 29 March 2012; accepted 16 April 2012; online 21 April 2012)

In the title coordination polymer, [Cd(C₈H₅N₂O₂S)₂(C₁₀H₈N₂)]_n, the Cd^II ion is coordinated by a bidentate 2,2-bipyridyl ligand, two O,O′-chelating 2-amino-1,3-benzothiazole-6-carboxylate (ABTC) ligands and one N-bonded ABTC ligand. The resulting CdN₃O₄ coordination polyhedron approximates to a very distorted pentagonal bipramid with one O and one N atom in axial positions. One of the ABTC ligands is bridging to an adjacent metal atom, generating an infinite chain propagating in [100]. A three-dimensional network is constructed from N—H⋯O and N—H⋯N hydrogen bonds and aromatic π–π stacking interactions [centroid–centroid separations = 3.641 (2) and 3.682 (3) Å].

Related literature

For our recent work on the design and sythesis of benzothiazole coordination networks, see: Fang et al. (2010 ); Lei et al. (2010 ). For the synthesis of the ligand, see: Das et al. (2003 ).

Experimental

Crystal data

[Cd(C₈H₅N₂O₂S)₂(C₁₀H₈N₂)]
M_r = 640.87
Triclinic, $[P \overline 1]$
a = 9.977 (2) Å
b = 11.715 (2) Å
c = 11.734 (2) Å
α = 65.28 (3)°
β = 77.52 (3)°
γ = 77.15 (3)°
V = 1202.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 173 K
0.27 × 0.18 × 0.13 mm

Data collection

Rigaku Saturn 724 CCD area-detector diffractometer
Absorption correction: numerical (NUMABS; Higashi, 2000 ) T_min = 0.837, T_max = 1.000
10158 measured reflections
5296 independent reflections
5015 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.088
S = 1.08
5296 reflections
352 parameters
H-atom parameters constrained
Δρ_max = 1.50 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—N3	2.345 (3)
Cd1—O3ⁱ	2.372 (2)
Cd1—O1	2.381 (3)
Cd1—N1	2.391 (3)
Cd1—O2	2.415 (3)
Cd1—O4ⁱ	2.422 (2)
Cd1—N2	2.484 (3)
Symmetry code: (i) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯O3ⁱⁱ	0.88	2.10	2.917 (4)	155
N6—H6B⋯O3ⁱⁱⁱ	0.88	2.12	2.996 (4)	173
N4—H4A⋯O4ⁱ	0.88	2.25	3.101 (4)	162
N4—H4B⋯N5^iv	0.88	2.21	3.066 (4)	163
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+2, -z-1; (iii) x+1, y, z-1; (iv) x, y-1, z+1.

Data collection: CrystalClear (Rigaku, 2007 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681201642X/hb6715sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201642X/hb6715Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of benzothiaole-based coordination networks (Fang et al., 2010; Lei et al., 2010), we now report the structure of a coordination polymer of cadmium and 2-amino-1,3-benzothiazole-6-carboxylate (ABTC) with 2,2'-bipyridine (bpy) as second ligand.

The polymer is a triclinic system crystal and it crystallizes in the space group of P-1. In the asymmetric unit (Fig. 1), center Cd (II) is seven-coordinated with (κ1, κ2)-µ2 coordination model, where one bpy provides two N atoms, one ABTC affords two O atoms, and the another ABTC affords two O atoms and one N atom of thiazole. The four Cd—O bonds are Cd1—O1, Cd1—O2, Cd1—O3, and Cd1—O4, with distance of 2.380 (7) Å, 2.415 (7) Å, 2.371 (3) Å, and 2.422 (6) Å, respectively. The three Cd—N bonds are Cd1—N1, Cd1—N2, and Cd1—N3, with distance of 2.390 (8) Å, 2.484 (1) Å, and 2.345 (6) Å, respectively, where the Cd1—N2 distance is slightly longer than common distance of Cd and N.

The asymmetric units are forming chains extending along the a axis (Fig. 2), through the one ABTC coordinated to two Cd(II) simultaneously by O from carboxylate and N from thiazole ring, respectively. Furthermore, three-dimensional supermolecular net (Fig. 3) are constructed by hydrogen bonds, as listed in Table 1, and π-π interactions [between thiazole and benzene rings (with certroid-centroid distance of 3.682 (3) Å and centroid-ring plane distance of 3.350 (9) and 3.404 (3) Å), and between the thiazole and bpy rings (with certroid-centroid distance of 3.641 (2) Å and centroid-ring plane distance of 3.478 (9) and 3.331 (7) Å)].

Related literature top

For our recent work on the design and sythesis of benzothiazole coordination networks, see: Fang et al. (2010); Lei et al. (2010). For the synthesis of the ligand, see: Das et al. (2003).

Experimental top

The 2-aminobenzothiazole-6-carboxylic acid ligand was obtained by hydrolyzing of ethyl-2-amion-1,3-benzothiazole-6-carboxylate (Das et al. 2003). The mixture of cadmium carbonate (0.0172 g, 0.1 mol), 2-aminobenzothiazole-6-carboxylic acid (0.0388 g, 0.2 mol), 2,2'-bipyridine (0.0160 g, 0.1 mol) and H₂O (8 ml) was sealed in a 23 ml stainless-steel reactor with Teflon liner and heated (283 K per hour) from room temperature to 423 K and kept at 423 K for 4 days, then cooled (279 K per hour) to room temperature. Colorless prisms were obtained.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The coordination environment of Cd atom, drawn with 50% probability displacement ellipsoids. [Symmetry codes: (i)1 + x,y,z; (ii)-1 + x,y,z]
	Fig. 2. A Chain formed by Cd1—N3 bond. H atoms are omitted.
	Fig. 3. Three-dimensional net with hydrogen bonds and π-π interactions. H atoms are omitted except those forming hydrogen bonds.

catena-Poly[[(2-amino-1,3-benzothiazole-6-carboxylato- κ²O,O')(2,2'-bipyridyl-κ²N,N')cadmium]- µ-2-amino-1,3-benzothiazole-6-carboxylato-κ³N¹:O,O'] top

Crystal data top

[Cd(C₈H₅N₂O₂S)₂(C₁₀H₈N₂)]	Z = 2
M_r = 640.87	F(000) = 656.0
Triclinic, P1	D_x = 1.770 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.977 (2) Å	Cell parameters from 4682 reflections
b = 11.715 (2) Å	θ = 3.1–27.6°
c = 11.734 (2) Å	µ = 1.13 mm⁻¹
α = 65.28 (3)°	T = 173 K
β = 77.52 (3)°	Prism, colourless
γ = 77.15 (3)°	0.27 × 0.18 × 0.13 mm
V = 1202.8 (4) Å³

Data collection top

Rigaku Saturn 724 CCD area-detector diffractometer	5296 independent reflections
Radiation source: fine-focus sealed tube	5015 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.6°, θ_min = 3.6°
dtprofit.ref scans	h = −12→12
Absorption correction: numerical (NUMABS; Higashi, 2000)	k = −14→15
T_min = 0.837, T_max = 1.000	l = −14→15
10158 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0263P)² + 2.5814P] where P = (F_o² + 2F_c²)/3
5296 reflections	(Δ/σ)_max = 0.001
352 parameters	Δρ_max = 1.50 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Cd(C₈H₅N₂O₂S)₂(C₁₀H₈N₂)]	γ = 77.15 (3)°
M_r = 640.87	V = 1202.8 (4) Å³
Triclinic, P1	Z = 2
a = 9.977 (2) Å	Mo Kα radiation
b = 11.715 (2) Å	µ = 1.13 mm⁻¹
c = 11.734 (2) Å	T = 173 K
α = 65.28 (3)°	0.27 × 0.18 × 0.13 mm
β = 77.52 (3)°

Data collection top

Rigaku Saturn 724 CCD area-detector diffractometer	5296 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 2000)	5015 reflections with I > 2σ(I)
T_min = 0.837, T_max = 1.000	R_int = 0.037
10158 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.08	Δρ_max = 1.50 e Å⁻³
5296 reflections	Δρ_min = −0.72 e Å⁻³
352 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
Cd1	0.30365 (2)	0.70429 (2)	0.09531 (2)	0.01412 (8)
S2	0.41833 (9)	0.83130 (8)	−0.62591 (8)	0.01725 (17)
O1	0.3596 (3)	0.7157 (2)	−0.1166 (2)	0.0248 (6)
O2	0.2554 (3)	0.8927 (3)	−0.0912 (2)	0.0271 (6)
N1	0.1528 (3)	0.8327 (3)	0.1983 (3)	0.0155 (6)
N2	0.2833 (3)	0.5972 (3)	0.3298 (3)	0.0180 (6)
N5	0.3521 (3)	1.0786 (3)	−0.6983 (3)	0.0158 (6)
N6	0.4267 (3)	1.0043 (3)	−0.8634 (3)	0.0213 (6)
H6A	0.4161	1.0813	−0.9227	0.026*
H6B	0.4567	0.9382	−0.8844	0.026*
S1	0.06488 (8)	0.34375 (7)	0.19139 (8)	0.01547 (16)
N3	0.1635 (3)	0.5537 (3)	0.1288 (3)	0.0140 (5)
N4	0.3306 (3)	0.3686 (3)	0.1717 (3)	0.0178 (6)
H4A	0.3994	0.4110	0.1563	0.021*
H4B	0.3471	0.2856	0.1940	0.021*
O4	−0.4784 (2)	0.5623 (2)	0.1301 (2)	0.0175 (5)
O3	−0.4823 (2)	0.7664 (2)	0.0858 (2)	0.0172 (5)
C1	0.1130 (3)	0.9574 (3)	0.1355 (3)	0.0179 (7)
H1	0.1300	0.9911	0.0456	0.021*
C2	0.0484 (4)	1.0395 (3)	0.1951 (3)	0.0196 (7)
H2	0.0224	1.1273	0.1470	0.023*
C3	0.0224 (4)	0.9910 (3)	0.3263 (3)	0.0201 (7)
H3	−0.0199	1.0452	0.3699	0.024*
C4	0.0592 (3)	0.8621 (3)	0.3925 (3)	0.0195 (7)
H4	0.0400	0.8262	0.4824	0.023*
C5	0.1251 (3)	0.7848 (3)	0.3261 (3)	0.0160 (6)
C6	0.1758 (4)	0.6489 (3)	0.3931 (3)	0.0171 (7)
C7	0.1184 (4)	0.5801 (4)	0.5154 (3)	0.0245 (8)
H7	0.0404	0.6179	0.5569	0.029*
C8	0.1773 (4)	0.4542 (4)	0.5763 (3)	0.0267 (8)
H8	0.1392	0.4042	0.6596	0.032*
C9	0.2915 (4)	0.4038 (3)	0.5134 (3)	0.0249 (8)
H9	0.3361	0.3195	0.5541	0.030*
C10	0.3402 (4)	0.4771 (3)	0.3908 (4)	0.0236 (7)
H10	0.4178	0.4408	0.3475	0.028*
C11	0.0212 (3)	0.5869 (3)	0.1247 (3)	0.0144 (6)
C12	−0.0528 (3)	0.7099 (3)	0.0958 (3)	0.0155 (6)
H12	−0.0063	0.7795	0.0771	0.019*
C13	−0.1952 (3)	0.7287 (3)	0.0949 (3)	0.0163 (6)
H13	−0.2461	0.8115	0.0777	0.020*
C14	−0.2650 (3)	0.6284 (3)	0.1187 (3)	0.0150 (6)
C15	−0.1930 (3)	0.5050 (3)	0.1483 (3)	0.0147 (6)
H15	−0.2395	0.4360	0.1651	0.018*
C16	−0.0512 (3)	0.4864 (3)	0.1522 (3)	0.0135 (6)
C17	0.2006 (3)	0.4302 (3)	0.1613 (3)	0.0139 (6)
C18	0.3359 (3)	1.0268 (3)	−0.5664 (3)	0.0163 (6)
C19	0.2953 (4)	1.0964 (3)	−0.4897 (3)	0.0193 (7)
H19	0.2735	1.1864	−0.5264	0.023*
C20	0.2872 (3)	1.0324 (3)	−0.3587 (3)	0.0191 (7)
H20	0.2600	1.0796	−0.3064	0.023*
C21	0.3182 (3)	0.9002 (3)	−0.3027 (3)	0.0176 (7)
C22	0.3572 (3)	0.8301 (3)	−0.3795 (3)	0.0183 (7)
H22	0.3774	0.7400	−0.3426	0.022*
C23	0.3659 (3)	0.8933 (3)	−0.5094 (3)	0.0161 (6)
C24	0.3974 (3)	0.9876 (3)	−0.7413 (3)	0.0172 (7)
C25	0.3105 (3)	0.8324 (3)	−0.1607 (3)	0.0187 (7)
C26	−0.4178 (3)	0.6531 (3)	0.1118 (3)	0.0136 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.01171 (12)	0.01595 (13)	0.01451 (12)	−0.00318 (9)	−0.00112 (8)	−0.00551 (9)
S2	0.0197 (4)	0.0161 (4)	0.0165 (4)	−0.0033 (3)	−0.0023 (3)	−0.0066 (3)
O1	0.0318 (15)	0.0235 (13)	0.0170 (12)	−0.0069 (11)	−0.0032 (11)	−0.0045 (10)
O2	0.0271 (14)	0.0345 (15)	0.0163 (12)	0.0047 (12)	−0.0040 (11)	−0.0107 (11)
N1	0.0119 (13)	0.0193 (14)	0.0155 (13)	−0.0037 (11)	−0.0031 (11)	−0.0057 (11)
N2	0.0215 (15)	0.0161 (14)	0.0160 (13)	−0.0020 (11)	−0.0040 (11)	−0.0057 (11)
N5	0.0151 (14)	0.0150 (13)	0.0162 (13)	−0.0039 (11)	−0.0023 (11)	−0.0042 (11)
N6	0.0279 (16)	0.0182 (14)	0.0164 (14)	−0.0030 (12)	0.0008 (12)	−0.0075 (12)
S1	0.0135 (4)	0.0134 (4)	0.0192 (4)	−0.0021 (3)	−0.0022 (3)	−0.0061 (3)
N3	0.0088 (13)	0.0160 (13)	0.0164 (13)	−0.0019 (10)	−0.0019 (10)	−0.0055 (11)
N4	0.0134 (13)	0.0166 (14)	0.0221 (14)	−0.0005 (11)	−0.0021 (11)	−0.0074 (11)
O4	0.0112 (11)	0.0196 (12)	0.0232 (12)	−0.0049 (9)	−0.0019 (9)	−0.0086 (10)
O3	0.0142 (11)	0.0171 (11)	0.0198 (12)	−0.0035 (9)	−0.0024 (9)	−0.0061 (9)
C1	0.0201 (17)	0.0195 (16)	0.0151 (15)	−0.0069 (14)	−0.0032 (13)	−0.0053 (13)
C2	0.0195 (17)	0.0151 (16)	0.0229 (17)	−0.0007 (13)	−0.0034 (14)	−0.0069 (13)
C3	0.0178 (17)	0.0219 (17)	0.0222 (17)	−0.0016 (14)	−0.0015 (14)	−0.0113 (14)
C4	0.0172 (17)	0.0248 (18)	0.0160 (16)	−0.0001 (14)	−0.0013 (13)	−0.0094 (14)
C5	0.0128 (15)	0.0195 (16)	0.0155 (15)	−0.0036 (13)	−0.0018 (12)	−0.0061 (13)
C6	0.0182 (17)	0.0178 (16)	0.0170 (16)	−0.0017 (13)	−0.0053 (13)	−0.0076 (13)
C7	0.028 (2)	0.0244 (18)	0.0159 (16)	0.0004 (15)	−0.0001 (15)	−0.0068 (14)
C8	0.038 (2)	0.0246 (19)	0.0149 (16)	−0.0051 (16)	−0.0040 (15)	−0.0046 (14)
C9	0.033 (2)	0.0175 (17)	0.0215 (18)	0.0008 (15)	−0.0111 (16)	−0.0038 (14)
C10	0.0255 (19)	0.0206 (17)	0.0261 (18)	0.0006 (15)	−0.0077 (15)	−0.0105 (15)
C11	0.0148 (16)	0.0154 (15)	0.0126 (14)	−0.0040 (12)	−0.0028 (12)	−0.0038 (12)
C12	0.0189 (17)	0.0134 (15)	0.0138 (15)	−0.0058 (13)	−0.0024 (12)	−0.0034 (12)
C13	0.0179 (17)	0.0167 (16)	0.0132 (15)	−0.0043 (13)	−0.0015 (12)	−0.0042 (12)
C14	0.0142 (16)	0.0186 (16)	0.0120 (14)	−0.0039 (13)	−0.0017 (12)	−0.0054 (12)
C15	0.0176 (16)	0.0155 (15)	0.0129 (14)	−0.0064 (13)	0.0005 (12)	−0.0066 (12)
C16	0.0139 (15)	0.0133 (15)	0.0117 (14)	−0.0019 (12)	−0.0014 (12)	−0.0034 (12)
C17	0.0119 (15)	0.0186 (16)	0.0116 (14)	−0.0017 (12)	−0.0017 (12)	−0.0065 (12)
C18	0.0146 (16)	0.0208 (17)	0.0151 (15)	−0.0058 (13)	−0.0010 (12)	−0.0075 (13)
C19	0.0180 (17)	0.0204 (17)	0.0215 (17)	−0.0031 (14)	−0.0025 (14)	−0.0101 (14)
C20	0.0171 (17)	0.0240 (18)	0.0190 (16)	−0.0027 (14)	−0.0013 (13)	−0.0118 (14)
C21	0.0128 (16)	0.0245 (17)	0.0153 (16)	−0.0021 (13)	−0.0012 (13)	−0.0083 (13)
C22	0.0168 (17)	0.0170 (16)	0.0164 (16)	−0.0034 (13)	−0.0006 (13)	−0.0024 (13)
C23	0.0160 (16)	0.0172 (16)	0.0159 (15)	−0.0028 (13)	−0.0026 (13)	−0.0066 (13)
C24	0.0157 (16)	0.0204 (17)	0.0177 (16)	−0.0067 (13)	−0.0042 (13)	−0.0066 (13)
C25	0.0097 (15)	0.0285 (19)	0.0176 (16)	−0.0045 (14)	−0.0020 (13)	−0.0077 (14)
C26	0.0128 (15)	0.0168 (15)	0.0104 (14)	−0.0022 (12)	−0.0010 (12)	−0.0046 (12)

Geometric parameters (Å, º) top

Cd1—N3	2.345 (3)	C3—C4	1.384 (5)
Cd1—O3ⁱ	2.372 (2)	C3—H3	0.9500
Cd1—O1	2.381 (3)	C4—C5	1.401 (5)
Cd1—N1	2.391 (3)	C4—H4	0.9500
Cd1—O2	2.415 (3)	C5—C6	1.474 (5)
Cd1—O4ⁱ	2.422 (2)	C6—C7	1.386 (5)
Cd1—N2	2.484 (3)	C7—C8	1.395 (5)
S2—C23	1.739 (3)	C7—H7	0.9500
S2—C24	1.763 (4)	C8—C9	1.376 (5)
O1—C25	1.264 (4)	C8—H8	0.9500
O2—C25	1.258 (4)	C9—C10	1.376 (5)
N1—C1	1.342 (4)	C9—H9	0.9500
N1—C5	1.352 (4)	C10—H10	0.9500
N2—C10	1.339 (4)	C11—C12	1.402 (5)
N2—C6	1.346 (4)	C11—C16	1.404 (4)
N5—C24	1.316 (4)	C12—C13	1.390 (5)
N5—C18	1.392 (4)	C12—H12	0.9500
N6—C24	1.337 (4)	C13—C14	1.396 (4)
N6—H6A	0.8800	C13—H13	0.9500
N6—H6B	0.8800	C14—C15	1.397 (5)
S1—C16	1.753 (3)	C14—C26	1.500 (4)
S1—C17	1.758 (3)	C15—C16	1.390 (4)
N3—C17	1.318 (4)	C15—H15	0.9500
N3—C11	1.392 (4)	C18—C19	1.396 (5)
N4—C17	1.340 (4)	C18—C23	1.410 (5)
N4—H4A	0.8800	C19—C20	1.393 (5)
N4—H4B	0.8800	C19—H19	0.9500
O4—C26	1.258 (4)	C20—C21	1.396 (5)
O4—Cd1ⁱⁱ	2.422 (2)	C20—H20	0.9500
O3—C26	1.279 (4)	C21—C22	1.401 (5)
O3—Cd1ⁱⁱ	2.372 (2)	C21—C25	1.509 (5)
C1—C2	1.387 (5)	C22—C23	1.380 (5)
C1—H1	0.9500	C22—H22	0.9500
C2—C3	1.386 (5)	C26—Cd1ⁱⁱ	2.742 (3)
C2—H2	0.9500

N3—Cd1—O3ⁱ	153.13 (9)	N1—C5—C6	116.9 (3)
N3—Cd1—O1	85.88 (10)	C4—C5—C6	121.3 (3)
O3ⁱ—Cd1—O1	92.07 (9)	N2—C6—C7	122.2 (3)
N3—Cd1—N1	101.19 (9)	N2—C6—C5	116.1 (3)
O3ⁱ—Cd1—N1	99.05 (9)	C7—C6—C5	121.7 (3)
O1—Cd1—N1	135.28 (9)	C6—C7—C8	118.7 (3)
N3—Cd1—O2	110.44 (10)	C6—C7—H7	120.6
O3ⁱ—Cd1—O2	89.76 (9)	C8—C7—H7	120.6
O1—Cd1—O2	54.93 (9)	C9—C8—C7	118.7 (3)
N1—Cd1—O2	81.78 (9)	C9—C8—H8	120.6
N3—Cd1—O4ⁱ	98.05 (9)	C7—C8—H8	120.6
O3ⁱ—Cd1—O4ⁱ	55.09 (8)	C8—C9—C10	119.1 (3)
O1—Cd1—O4ⁱ	85.33 (9)	C8—C9—H9	120.4
N1—Cd1—O4ⁱ	135.73 (9)	C10—C9—H9	120.4
O2—Cd1—O4ⁱ	127.19 (9)	N2—C10—C9	123.0 (3)
N3—Cd1—N2	80.49 (10)	N2—C10—H10	118.5
O3ⁱ—Cd1—N2	91.08 (9)	C9—C10—H10	118.5
O1—Cd1—N2	155.59 (9)	N3—C11—C12	125.5 (3)
N1—Cd1—N2	67.79 (10)	N3—C11—C16	115.7 (3)
O2—Cd1—N2	149.31 (9)	C12—C11—C16	118.8 (3)
O4ⁱ—Cd1—N2	76.72 (9)	C13—C12—C11	119.0 (3)
N3—Cd1—C25	99.34 (10)	C13—C12—H12	120.5
O3ⁱ—Cd1—C25	90.67 (9)	C11—C12—H12	120.5
O1—Cd1—C25	27.53 (9)	C12—C13—C14	121.5 (3)
N1—Cd1—C25	108.67 (10)	C12—C13—H13	119.3
O2—Cd1—C25	27.41 (10)	C14—C13—H13	119.3
O4ⁱ—Cd1—C25	106.96 (10)	C13—C14—C15	120.2 (3)
N2—Cd1—C25	176.27 (10)	C13—C14—C26	120.0 (3)
N3—Cd1—C26ⁱ	125.36 (10)	C15—C14—C26	119.8 (3)
O3ⁱ—Cd1—C26ⁱ	27.78 (9)	C16—C15—C14	118.0 (3)
O1—Cd1—C26ⁱ	88.58 (10)	C16—C15—H15	121.0
N1—Cd1—C26ⁱ	119.61 (9)	C14—C15—H15	121.0
O2—Cd1—C26ⁱ	110.00 (10)	C15—C16—C11	122.4 (3)
O4ⁱ—Cd1—C26ⁱ	27.31 (8)	C15—C16—S1	128.6 (2)
N2—Cd1—C26ⁱ	83.04 (10)	C11—C16—S1	109.0 (2)
C25—Cd1—C26ⁱ	99.99 (10)	N3—C17—N4	125.4 (3)
C23—S2—C24	88.73 (16)	N3—C17—S1	115.4 (2)
C25—O1—Cd1	92.0 (2)	N4—C17—S1	119.2 (2)
C25—O2—Cd1	90.5 (2)	N5—C18—C19	125.3 (3)
C1—N1—C5	118.0 (3)	N5—C18—C23	115.5 (3)
C1—N1—Cd1	121.9 (2)	C19—C18—C23	119.2 (3)
C5—N1—Cd1	119.2 (2)	C20—C19—C18	119.2 (3)
C10—N2—C6	118.1 (3)	C20—C19—H19	120.4
C10—N2—Cd1	123.5 (2)	C18—C19—H19	120.4
C6—N2—Cd1	114.9 (2)	C19—C20—C21	121.4 (3)
C24—N5—C18	109.9 (3)	C19—C20—H20	119.3
C24—N6—H6A	120.0	C21—C20—H20	119.3
C24—N6—H6B	120.0	C20—C21—C22	119.5 (3)
H6A—N6—H6B	120.0	C20—C21—C25	120.7 (3)
C16—S1—C17	89.23 (15)	C22—C21—C25	119.8 (3)
C17—N3—C11	110.7 (3)	C23—C22—C21	119.3 (3)
C17—N3—Cd1	127.6 (2)	C23—C22—H22	120.4
C11—N3—Cd1	121.6 (2)	C21—C22—H22	120.4
C17—N4—H4A	120.0	C22—C23—C18	121.4 (3)
C17—N4—H4B	120.0	C22—C23—S2	128.8 (3)
H4A—N4—H4B	120.0	C18—C23—S2	109.7 (2)
C26—O4—Cd1ⁱⁱ	90.62 (19)	N5—C24—N6	125.6 (3)
C26—O3—Cd1ⁱⁱ	92.41 (19)	N5—C24—S2	116.1 (3)
N1—C1—C2	123.4 (3)	N6—C24—S2	118.3 (3)
N1—C1—H1	118.3	O2—C25—O1	122.6 (3)
C2—C1—H1	118.3	O2—C25—C21	119.5 (3)
C3—C2—C1	118.6 (3)	O1—C25—C21	117.9 (3)
C3—C2—H2	120.7	O2—C25—Cd1	62.11 (18)
C1—C2—H2	120.7	O1—C25—Cd1	60.52 (18)
C4—C3—C2	118.8 (3)	C21—C25—Cd1	178.2 (2)
C4—C3—H3	120.6	O4—C26—O3	121.9 (3)
C2—C3—H3	120.6	O4—C26—C14	119.2 (3)
C3—C4—C5	119.5 (3)	O3—C26—C14	118.9 (3)
C3—C4—H4	120.3	O4—C26—Cd1ⁱⁱ	62.07 (17)
C5—C4—H4	120.3	O3—C26—Cd1ⁱⁱ	59.82 (16)
N1—C5—C4	121.7 (3)	C14—C26—Cd1ⁱⁱ	178.6 (2)

N3—Cd1—O1—C25	119.4 (2)	C17—N3—C11—C12	178.7 (3)
O3ⁱ—Cd1—O1—C25	−87.5 (2)	Cd1—N3—C11—C12	2.8 (4)
N1—Cd1—O1—C25	17.6 (3)	C17—N3—C11—C16	−1.3 (4)
O2—Cd1—O1—C25	0.78 (19)	Cd1—N3—C11—C16	−177.1 (2)
O4ⁱ—Cd1—O1—C25	−142.2 (2)	N3—C11—C12—C13	179.8 (3)
N2—Cd1—O1—C25	175.3 (2)	C16—C11—C12—C13	−0.3 (5)
C26ⁱ—Cd1—O1—C25	−115.0 (2)	C11—C12—C13—C14	−1.7 (5)
N3—Cd1—O2—C25	−70.0 (2)	C12—C13—C14—C15	2.1 (5)
O3ⁱ—Cd1—O2—C25	91.9 (2)	C12—C13—C14—C26	−177.5 (3)
O1—Cd1—O2—C25	−0.78 (19)	C13—C14—C15—C16	−0.4 (5)
N1—Cd1—O2—C25	−168.9 (2)	C26—C14—C15—C16	179.3 (3)
O4ⁱ—Cd1—O2—C25	48.1 (2)	C14—C15—C16—C11	−1.7 (5)
N2—Cd1—O2—C25	−176.38 (19)	C14—C15—C16—S1	177.6 (2)
C26ⁱ—Cd1—O2—C25	72.5 (2)	N3—C11—C16—C15	−178.1 (3)
N3—Cd1—N1—C1	−120.1 (2)	C12—C11—C16—C15	2.0 (5)
O3ⁱ—Cd1—N1—C1	77.7 (2)	N3—C11—C16—S1	2.6 (3)
O1—Cd1—N1—C1	−24.6 (3)	C12—C11—C16—S1	−177.4 (2)
O2—Cd1—N1—C1	−10.7 (2)	C17—S1—C16—C15	178.3 (3)
O4ⁱ—Cd1—N1—C1	125.9 (2)	C17—S1—C16—C11	−2.4 (2)
N2—Cd1—N1—C1	165.2 (3)	C11—N3—C17—N4	178.8 (3)
C25—Cd1—N1—C1	−16.1 (3)	Cd1—N3—C17—N4	−5.6 (5)
C26ⁱ—Cd1—N1—C1	97.6 (3)	C11—N3—C17—S1	−0.7 (3)
N3—Cd1—N1—C5	71.2 (2)	Cd1—N3—C17—S1	174.85 (14)
O3ⁱ—Cd1—N1—C5	−91.0 (2)	C16—S1—C17—N3	1.8 (3)
O1—Cd1—N1—C5	166.7 (2)	C16—S1—C17—N4	−177.7 (3)
O2—Cd1—N1—C5	−179.5 (2)	C24—N5—C18—C19	177.1 (3)
O4ⁱ—Cd1—N1—C5	−42.9 (3)	C24—N5—C18—C23	−1.9 (4)
N2—Cd1—N1—C5	−3.6 (2)	N5—C18—C19—C20	−178.1 (3)
C25—Cd1—N1—C5	175.2 (2)	C23—C18—C19—C20	0.9 (5)
C26ⁱ—Cd1—N1—C5	−71.1 (3)	C18—C19—C20—C21	−0.3 (5)
N3—Cd1—N2—C10	67.9 (3)	C19—C20—C21—C22	−0.6 (5)
O3ⁱ—Cd1—N2—C10	−86.4 (3)	C19—C20—C21—C25	179.3 (3)
O1—Cd1—N2—C10	11.0 (4)	C20—C21—C22—C23	0.8 (5)
N1—Cd1—N2—C10	174.2 (3)	C25—C21—C22—C23	−179.0 (3)
O2—Cd1—N2—C10	−177.8 (2)	C21—C22—C23—C18	−0.2 (5)
O4ⁱ—Cd1—N2—C10	−32.8 (3)	C21—C22—C23—S2	176.9 (3)
C25—Cd1—N2—C10	155.6 (14)	N5—C18—C23—C22	178.5 (3)
C26ⁱ—Cd1—N2—C10	−59.8 (3)	C19—C18—C23—C22	−0.6 (5)
N3—Cd1—N2—C6	−90.6 (2)	N5—C18—C23—S2	0.8 (4)
O3ⁱ—Cd1—N2—C6	115.1 (2)	C19—C18—C23—S2	−178.3 (3)
O1—Cd1—N2—C6	−147.5 (2)	C24—S2—C23—C22	−177.1 (3)
N1—Cd1—N2—C6	15.7 (2)	C24—S2—C23—C18	0.3 (3)
O2—Cd1—N2—C6	23.7 (3)	C18—N5—C24—N6	−178.6 (3)
O4ⁱ—Cd1—N2—C6	168.7 (2)	C18—N5—C24—S2	2.2 (4)
C25—Cd1—N2—C6	−2.9 (16)	C23—S2—C24—N5	−1.5 (3)
C26ⁱ—Cd1—N2—C6	141.7 (2)	C23—S2—C24—N6	179.2 (3)
O3ⁱ—Cd1—N3—C17	0.5 (4)	Cd1—O2—C25—O1	1.4 (3)
O1—Cd1—N3—C17	86.9 (3)	Cd1—O2—C25—C21	−179.1 (3)
N1—Cd1—N3—C17	−137.7 (3)	Cd1—O1—C25—O2	−1.5 (3)
O2—Cd1—N3—C17	137.0 (3)	Cd1—O1—C25—C21	179.1 (3)
O4ⁱ—Cd1—N3—C17	2.3 (3)	C20—C21—C25—O2	11.1 (5)
N2—Cd1—N3—C17	−72.7 (3)	C22—C21—C25—O2	−169.0 (3)
C25—Cd1—N3—C17	111.0 (3)	C20—C21—C25—O1	−169.4 (3)
C26ⁱ—Cd1—N3—C17	1.6 (3)	C22—C21—C25—O1	10.4 (5)
O3ⁱ—Cd1—N3—C11	175.6 (2)	C20—C21—C25—Cd1	−144 (8)
O1—Cd1—N3—C11	−97.9 (2)	C22—C21—C25—Cd1	36 (8)
N1—Cd1—N3—C11	37.5 (2)	N3—Cd1—C25—O2	116.9 (2)
O2—Cd1—N3—C11	−47.8 (2)	O3ⁱ—Cd1—C25—O2	−88.2 (2)
O4ⁱ—Cd1—N3—C11	177.4 (2)	O1—Cd1—C25—O2	178.6 (3)
N2—Cd1—N3—C11	102.4 (2)	N1—Cd1—C25—O2	11.6 (2)
C25—Cd1—N3—C11	−73.8 (2)	O4ⁱ—Cd1—C25—O2	−141.69 (19)
C26ⁱ—Cd1—N3—C11	176.8 (2)	N2—Cd1—C25—O2	29.8 (16)
C5—N1—C1—C2	1.7 (5)	C26ⁱ—Cd1—C25—O2	−114.5 (2)
Cd1—N1—C1—C2	−167.2 (3)	N3—Cd1—C25—O1	−61.8 (2)
N1—C1—C2—C3	−0.4 (5)	O3ⁱ—Cd1—C25—O1	93.2 (2)
C1—C2—C3—C4	−1.3 (5)	N1—Cd1—C25—O1	−167.02 (19)
C2—C3—C4—C5	1.8 (5)	O2—Cd1—C25—O1	−178.6 (3)
C1—N1—C5—C4	−1.2 (5)	O4ⁱ—Cd1—C25—O1	39.7 (2)
Cd1—N1—C5—C4	168.0 (2)	N2—Cd1—C25—O1	−148.9 (14)
C1—N1—C5—C6	−177.1 (3)	C26ⁱ—Cd1—C25—O1	66.9 (2)
Cd1—N1—C5—C6	−8.0 (4)	N3—Cd1—C25—C21	−88 (8)
C3—C4—C5—N1	−0.5 (5)	O3ⁱ—Cd1—C25—C21	67 (8)
C3—C4—C5—C6	175.2 (3)	O1—Cd1—C25—C21	−26 (8)
C10—N2—C6—C7	−3.6 (5)	N1—Cd1—C25—C21	167 (8)
Cd1—N2—C6—C7	156.1 (3)	O2—Cd1—C25—C21	155 (8)
C10—N2—C6—C5	174.5 (3)	O4ⁱ—Cd1—C25—C21	14 (8)
Cd1—N2—C6—C5	−25.7 (4)	N2—Cd1—C25—C21	−175 (7)
N1—C5—C6—N2	23.0 (4)	C26ⁱ—Cd1—C25—C21	41 (8)
C4—C5—C6—N2	−153.0 (3)	Cd1ⁱⁱ—O4—C26—O3	−0.3 (3)
N1—C5—C6—C7	−158.8 (3)	Cd1ⁱⁱ—O4—C26—C14	−179.3 (2)
C4—C5—C6—C7	25.2 (5)	Cd1ⁱⁱ—O3—C26—O4	0.3 (3)
N2—C6—C7—C8	2.2 (6)	Cd1ⁱⁱ—O3—C26—C14	179.3 (2)
C5—C6—C7—C8	−175.8 (3)	C13—C14—C26—O4	178.0 (3)
C6—C7—C8—C9	1.1 (6)	C15—C14—C26—O4	−1.6 (4)
C7—C8—C9—C10	−2.8 (6)	C13—C14—C26—O3	−1.0 (4)
C6—N2—C10—C9	1.7 (5)	C15—C14—C26—O3	179.4 (3)
Cd1—N2—C10—C9	−156.1 (3)	C13—C14—C26—Cd1ⁱⁱ	25 (9)
C8—C9—C10—N2	1.5 (6)	C15—C14—C26—Cd1ⁱⁱ	−155 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O3ⁱⁱⁱ	0.88	2.10	2.917 (4)	155
N6—H6B···O3^iv	0.88	2.12	2.996 (4)	173
N4—H4A···O4ⁱ	0.88	2.25	3.101 (4)	162
N4—H4B···N5^v	0.88	2.21	3.066 (4)	163

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

Experimental details

Crystal data
Chemical formula	[Cd(C₈H₅N₂O₂S)₂(C₁₀H₈N₂)]
M_r	640.87
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.977 (2), 11.715 (2), 11.734 (2)
α, β, γ (°)	65.28 (3), 77.52 (3), 77.15 (3)
V (Å³)	1202.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.27 × 0.18 × 0.13

Data collection
Diffractometer	Rigaku Saturn 724 CCD area-detector diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 2000)
T_min, T_max	0.837, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10158, 5296, 5015
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.088, 1.08
No. of reflections	5296
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.50, −0.72

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEX (McArdle, 1995).

Selected bond lengths (Å) top

Cd1—N3	2.345 (3)	Cd1—O2	2.415 (3)
Cd1—O3ⁱ	2.372 (2)	Cd1—O4ⁱ	2.422 (2)
Cd1—O1	2.381 (3)	Cd1—N2	2.484 (3)
Cd1—N1	2.391 (3)

Symmetry code: (i) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O3ⁱⁱ	0.88	2.10	2.917 (4)	155
N6—H6B···O3ⁱⁱⁱ	0.88	2.12	2.996 (4)	173
N4—H4A···O4ⁱ	0.88	2.25	3.101 (4)	162
N4—H4B···N5^iv	0.88	2.21	3.066 (4)	163

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

Acknowledgements

The authors gratefully acknowledge financial support from the Foundations of Fuzhou University (2010-XQ-06) and the Education Department of Fujian Province (JA11020).

References

Das, J., Lin, J., Moquin, R. V., Shen, Z., Spergel, S. H., Wityak, J., Doweyko, A. M., DeFex, H. F., Fang, Q., Pang, S., Pitt, S., Shen, D. R., Schieven, G. L. & Barrish, J. C. (2003). Bioorg. Med. Chem. Lett. 13, 2145–2149. Web of Science CrossRef PubMed CAS Google Scholar
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