Tris(2-amino-1,3-thia­zole-κN3)(7-oxa­bicyclo­[2.2.1]heptane-2,3-dicarboxyl­ato-κ3O2,O3,O7)cadmium(II) dihydrate

Wang, N.; Wu, Y.-Z.; Lin, Q.-Y.

doi:10.1107/S1600536810027170

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages m961-m962

https://doi.org/10.1107/S1600536810027170

Open

access

Tris(2-amino-1,3-thiazole-κN³)(7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylato-κ³O²,O³,O⁷)cadmium(II) dihydrate

Na Wang,^a,^b Yi-Zhou Wu ^c and Qiu-Yue Lin ^a,^b ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, ^bCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and ^cCollege of Public Administration, Zhejiang University, Hangzhou, 310027, Zhejiang , People's Republic of China
^*Correspondence e-mail: sky51@zjnu.cn

(Received 15 June 2010; accepted 8 July 2010; online 17 July 2010)

In the crystal structure of the title complex, [Cd(C₈H₈O₅)(C₃H₄N₂S)₃]·2H₂O, the Cd^II atom exhibits a slightly distorted octahedral CdO₃N₃ coordination, defined by the bridging O atom of the bicycloheptane unit, two O atoms from the carboxylate groups and by three N atoms from three 2-aminothiazole ligands. Uncoordinated lattice water molecules are also present in the crystal structure. N—H⋯O and O—H⋯O hydrogen-bonding interactions link the components into a three-dimensional structure.

Related literature

For synthetic aspects, see: Yin et al. (2003 ). For background to 7-oxabicyclo(2,2,1) heptane-2,3-dicarboxylic anhydride (norcantharidin), see: Shimi et al. (1982 ).

Experimental

Crystal data

[Cd(C₈H₈O₅)(C₃H₄N₂S)₃]·2H₂O
M_r = 633.00
Monoclinic, P 2₁ /c
a = 9.6457 (3) Å
b = 9.9255 (3) Å
c = 25.4653 (9) Å
β = 101.980 (2)°
V = 2384.91 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 296 K
0.08 × 0.08 × 0.04 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.90, T_max = 0.95
19757 measured reflections
5480 independent reflections
2777 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.119
S = 1.01
5480 reflections
319 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—O4	2.268 (4)
Cd1—N4	2.302 (5)
Cd1—N2	2.305 (5)
Cd1—O2	2.312 (4)
Cd1—N6	2.341 (5)
Cd1—O1	2.467 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86	2.04	2.867 (6)	161
N1—H1B⋯O3ⁱ	0.86	2.19	2.931 (6)	144
N3—H3B⋯O4	0.86	2.00	2.803 (7)	156
N3—H3C⋯O1Wⁱⁱ	0.86	2.14	2.965 (7)	160
N5—H5B⋯O1	0.86	2.15	2.917 (7)	149
N5—H5C⋯O3ⁱⁱⁱ	0.86	2.46	3.177 (7)	141
N5—H5C⋯O2W^iv	0.86	2.47	3.052 (9)	125
O1W—H1⋯O5^v	0.86 (2)	1.97 (2)	2.817 (6)	174 (7)
O1W—H2⋯O3^vi	0.85 (2)	2.03 (2)	2.865 (6)	168 (6)
O2W—H3⋯O5^vii	0.86 (6)	2.25 (6)	2.996 (9)	145 (9)
O2W—H4⋯O5	0.88 (7)	2.12 (4)	2.962 (10)	162 (12)
Symmetry codes: (i) -x, -y+2, -z; (ii) x-1, y, z; (iii) x+1, y, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) x+1, y-1, z; (vii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810027170/wm2366sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027170/wm2366Isup2.hkl

checkCIF report

Comment top

7-oxabicyclo(2,2,1) heptane-2,3-dicarboxylic anhydride (norcantharidin), a traditional Chinese drug, has a great inhibitive effect on various cancer cells (Shimi et al., 1982) which makes norcantharidin and its derivatives interesting compounds. Cadmium acetate can react with 2-aminothiazole and disodium demethylcantharate to form the title compound, [Cd(C₈H₈O₅)(C₃H₄N₂S)₃]^.2H₂O.

The Cd^II atom exhibits a slightly distorted octahedral CdO₃N₃ coordination (Fig. 1), defined by the bridging O atom of the bicycloheptane unit, two O atoms from the carboxylate groups and by three N atoms from three different 2-aminothiazole ligands. O4, N6, N2 and O2 define the equatorial plane; O1 and N4 are in the axial positions. The bond angle O1—Cd1—N4 of 171.27 (14)° is indicative of the polyhedral distortion. Owing to the binding of the bridging oxygen atom to the Cd^II atom, two six-membered rings (Cd1—O1—C6—C4—C2—O2) and (Cd1—O1—C5—C3—C1—O4) are created. In addition, a seven-membered ring (Cd1—O2—C2—C4—C3—C1—O4) is formed which helps to stabilize the complex.

Uncoordinated lattice water molecules are also present in the crystal structure. N—H···O and O—H···O hydrogen-bonding interactions link the components into a three-dimensional structure.

Related literature top

For synthetic aspects, see: Yin et al. (2003). For background to 7-oxabicyclo(2,2,1) heptane-2,3-dicarboxylic anhydride (norcantharidin), see: Shimi et al. (1982).

Experimental top

Disodium demethylcantharate was prepared according to literature procedures (Yin et al., 2003). Cadmium acetate, disodium demethylcantharate and 2-aminothiazole were dissolved in 15 ml distilled water. The mixture was sealed in a 25 ml Teflon-lined stainless vessel and heated at 443 K for 3 d, then cooled slowly to room temperature. Crystal suitable for X-ray diffraction were obtained.

Structure description top

Uncoordinated lattice water molecules are also present in the crystal structure. N—H···O and O—H···O hydrogen-bonding interactions link the components into a three-dimensional structure.

For synthetic aspects, see: Yin et al. (2003). For background to 7-oxabicyclo(2,2,1) heptane-2,3-dicarboxylic anhydride (norcantharidin), see: Shimi et al. (1982).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecule of the title compound, showing the atom-labelling scheme and displacement ellipsoids drawn at the 30% probability level.

Tris(2-amino-1,3-thiazole-κN³)(7-oxabicyclo[2.2.1]heptane-2,3- dicarboxylato-κ³O²,O³,O⁷)cadmium(II) dihydrate top

Crystal data top

[Cd(C₈H₈O₅)(C₃H₄N₂S)₃]·2H₂O	F(000) = 1280
M_r = 633.00	D_x = 1.763 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1039 reflections
a = 9.6457 (3) Å	θ = 1.6–27.6°
b = 9.9255 (3) Å	µ = 1.23 mm⁻¹
c = 25.4653 (9) Å	T = 296 K
β = 101.980 (2)°	Block, colorless
V = 2384.91 (13) Å³	0.08 × 0.08 × 0.04 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	5480 independent reflections
Radiation source: fine-focus sealed tube	2777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
φ– and ω–scans	θ_max = 27.6°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.90, T_max = 0.95	k = −12→11
19757 measured reflections	l = −32→33

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0267P)²] where P = (F_o² + 2F_c²)/3
5480 reflections	(Δ/σ)_max < 0.001
319 parameters	Δρ_max = 0.80 e Å⁻³
6 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Cd(C₈H₈O₅)(C₃H₄N₂S)₃]·2H₂O	V = 2384.91 (13) Å³
M_r = 633.00	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6457 (3) Å	µ = 1.23 mm⁻¹
b = 9.9255 (3) Å	T = 296 K
c = 25.4653 (9) Å	0.08 × 0.08 × 0.04 mm
β = 101.980 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	5480 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2777 reflections with I > 2σ(I)
T_min = 0.90, T_max = 0.95	R_int = 0.100
19757 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	6 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.80 e Å⁻³
5480 reflections	Δρ_min = −0.69 e Å⁻³
319 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	0.30795 (4)	0.70542 (5)	0.098525 (16)	0.03617 (15)
S1	0.40386 (19)	0.91245 (19)	−0.06279 (6)	0.0540 (5)
S2	0.07421 (19)	0.28302 (19)	0.04108 (8)	0.0595 (5)
S3	0.8009 (2)	0.5619 (2)	0.15111 (8)	0.0719 (6)
O1	0.4020 (4)	0.9069 (4)	0.15068 (14)	0.0396 (10)
O2	0.1101 (4)	0.8429 (4)	0.08458 (15)	0.0445 (11)
O3	−0.0541 (4)	0.9542 (5)	0.11418 (16)	0.0617 (14)
O4	0.2421 (5)	0.6604 (4)	0.17721 (17)	0.0540 (12)
O5	0.1018 (5)	0.7150 (5)	0.23232 (19)	0.0780 (16)
N1	0.1977 (5)	0.9502 (5)	−0.00787 (19)	0.0523 (15)
H1A	0.1565	0.9321	0.0182	0.063*
H1B	0.1637	1.0115	−0.0308	0.063*
N2	0.3724 (5)	0.7869 (5)	0.02228 (18)	0.0393 (12)
N3	0.1366 (5)	0.4106 (5)	0.1357 (2)	0.0573 (16)
H3B	0.1682	0.4755	0.1573	0.069*
H3C	0.0938	0.3437	0.1467	0.069*
N4	0.2092 (5)	0.5071 (5)	0.06150 (18)	0.0398 (12)
N5	0.6828 (6)	0.8058 (6)	0.1457 (3)	0.086 (2)
H5B	0.6122	0.8606	0.1404	0.104*
H5C	0.7680	0.8364	0.1540	0.104*
N6	0.5362 (5)	0.6186 (5)	0.12915 (18)	0.0429 (13)
C1	0.1932 (7)	0.7435 (7)	0.2067 (2)	0.0464 (18)
C2	0.0712 (7)	0.9216 (6)	0.1179 (2)	0.0381 (15)
C3	0.2499 (6)	0.8860 (7)	0.2105 (2)	0.0426 (16)
H3A	0.2369	0.9256	0.2444	0.051*
C4	0.1826 (6)	0.9839 (6)	0.1628 (2)	0.0401 (15)
H4A	0.1420	1.0626	0.1774	0.048*
C5	0.4063 (6)	0.8950 (7)	0.2080 (2)	0.0450 (17)
H5A	0.4625	0.8183	0.2248	0.054*
C6	0.3141 (6)	1.0263 (6)	0.1430 (2)	0.0442 (16)
H6A	0.2937	1.0590	0.1059	0.053*
C7	0.4675 (8)	1.0305 (8)	0.2285 (3)	0.069 (2)
H7A	0.5701	1.0302	0.2344	0.083*
H7B	0.4391	1.0553	0.2615	0.083*
C8	0.4029 (7)	1.1250 (7)	0.1828 (3)	0.061 (2)
H8A	0.4753	1.1685	0.1674	0.073*
H8B	0.3440	1.1933	0.1945	0.073*
C9	0.3141 (6)	0.8822 (6)	−0.0122 (2)	0.0368 (15)
C10	0.5278 (7)	0.7915 (7)	−0.0356 (2)	0.0503 (17)
H10A	0.6070	0.7679	−0.0492	0.060*
C11	0.4922 (6)	0.7378 (6)	0.0074 (2)	0.0449 (17)
H11A	0.5460	0.6696	0.0268	0.054*
C12	0.1458 (6)	0.4122 (7)	0.0845 (3)	0.0451 (16)
C13	0.1311 (7)	0.3632 (7)	−0.0100 (3)	0.0530 (18)
H13A	0.1162	0.3322	−0.0452	0.064*
C14	0.2003 (6)	0.4769 (7)	0.0078 (2)	0.0462 (17)
H14A	0.2400	0.5323	−0.0146	0.055*
C15	0.6606 (7)	0.6740 (7)	0.1417 (2)	0.0463 (18)
C16	0.6826 (8)	0.4331 (8)	0.1364 (3)	0.074 (2)
H16A	0.7062	0.3425	0.1352	0.088*
C17	0.5514 (8)	0.4817 (8)	0.1269 (3)	0.064 (2)
H17A	0.4731	0.4250	0.1190	0.076*
O1W	0.9253 (5)	0.2156 (5)	0.15966 (19)	0.0631 (13)
H1	0.922 (8)	0.211 (6)	0.1930 (10)	0.095*
H2	0.926 (8)	0.134 (3)	0.150 (2)	0.095*
O2W	0.1155 (7)	0.4230 (9)	0.2567 (3)	0.134 (3)
H3	0.031 (5)	0.395 (10)	0.257 (5)	0.200*
H4	0.101 (11)	0.503 (6)	0.242 (5)	0.200*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0370 (3)	0.0329 (3)	0.0398 (2)	0.0016 (2)	0.01077 (17)	−0.0009 (2)
S1	0.0660 (12)	0.0542 (13)	0.0446 (10)	−0.0029 (10)	0.0177 (9)	0.0082 (9)
S2	0.0546 (11)	0.0365 (12)	0.0867 (13)	−0.0082 (9)	0.0132 (10)	−0.0094 (10)
S3	0.0458 (12)	0.0877 (18)	0.0809 (14)	0.0263 (11)	0.0097 (10)	0.0158 (12)
O1	0.041 (3)	0.037 (3)	0.038 (2)	0.001 (2)	0.0041 (18)	0.004 (2)
O2	0.042 (3)	0.043 (3)	0.046 (2)	0.006 (2)	0.004 (2)	−0.011 (2)
O3	0.038 (3)	0.080 (4)	0.061 (3)	0.024 (3)	−0.004 (2)	−0.011 (3)
O4	0.068 (3)	0.041 (3)	0.059 (3)	−0.004 (2)	0.029 (2)	0.002 (2)
O5	0.088 (4)	0.076 (4)	0.088 (4)	−0.015 (3)	0.060 (3)	−0.012 (3)
N1	0.055 (4)	0.052 (4)	0.049 (3)	0.013 (3)	0.009 (3)	0.013 (3)
N2	0.046 (3)	0.032 (3)	0.040 (3)	0.004 (3)	0.009 (2)	0.000 (3)
N3	0.078 (4)	0.040 (4)	0.062 (4)	−0.014 (3)	0.033 (3)	0.000 (3)
N4	0.042 (3)	0.034 (3)	0.046 (3)	0.000 (2)	0.013 (2)	−0.001 (3)
N5	0.032 (3)	0.055 (5)	0.167 (7)	−0.012 (3)	0.007 (4)	0.022 (5)
N6	0.047 (4)	0.034 (4)	0.047 (3)	0.007 (3)	0.008 (2)	−0.002 (3)
C1	0.040 (4)	0.062 (6)	0.037 (4)	0.001 (3)	0.008 (3)	−0.001 (3)
C2	0.044 (4)	0.028 (4)	0.039 (4)	0.003 (3)	0.002 (3)	0.003 (3)
C3	0.047 (4)	0.045 (5)	0.035 (3)	0.000 (3)	0.007 (3)	−0.008 (3)
C4	0.036 (4)	0.038 (4)	0.046 (4)	0.007 (3)	0.009 (3)	−0.011 (3)
C5	0.043 (4)	0.051 (5)	0.035 (3)	0.000 (3)	−0.006 (3)	−0.003 (3)
C6	0.043 (4)	0.026 (4)	0.058 (4)	−0.001 (3)	−0.002 (3)	0.002 (3)
C7	0.068 (5)	0.074 (6)	0.056 (4)	−0.006 (4)	−0.011 (4)	−0.013 (4)
C8	0.057 (5)	0.041 (5)	0.077 (5)	−0.011 (4)	0.000 (4)	−0.013 (4)
C9	0.043 (4)	0.030 (4)	0.036 (3)	−0.003 (3)	0.006 (3)	−0.003 (3)
C10	0.058 (4)	0.050 (5)	0.048 (4)	0.007 (4)	0.024 (3)	0.004 (4)
C11	0.046 (4)	0.041 (5)	0.054 (4)	0.001 (3)	0.025 (3)	−0.002 (3)
C12	0.039 (4)	0.039 (5)	0.056 (4)	0.002 (3)	0.007 (3)	0.000 (3)
C13	0.052 (4)	0.049 (5)	0.056 (4)	−0.010 (4)	0.006 (3)	−0.013 (4)
C14	0.049 (4)	0.047 (5)	0.043 (4)	−0.001 (3)	0.012 (3)	0.001 (3)
C15	0.035 (4)	0.048 (5)	0.058 (4)	0.008 (3)	0.013 (3)	0.017 (4)
C16	0.066 (6)	0.058 (6)	0.087 (6)	0.021 (5)	−0.005 (4)	−0.016 (4)
C17	0.049 (5)	0.054 (6)	0.079 (5)	0.005 (4)	−0.006 (4)	−0.009 (4)
O1W	0.073 (3)	0.048 (3)	0.073 (3)	0.014 (3)	0.024 (3)	0.001 (3)
O2W	0.116 (6)	0.159 (8)	0.120 (5)	−0.020 (5)	0.011 (5)	0.032 (5)

Geometric parameters (Å, º) top

Cd1—O4	2.268 (4)	N6—C15	1.299 (7)
Cd1—N4	2.302 (5)	N6—C17	1.369 (8)
Cd1—N2	2.305 (5)	C1—C3	1.513 (9)
Cd1—O2	2.312 (4)	C2—C4	1.528 (8)
Cd1—N6	2.341 (5)	C3—C5	1.526 (8)
Cd1—O1	2.467 (4)	C3—C4	1.585 (8)
S1—C9	1.721 (6)	C3—H3A	0.9800
S1—C10	1.734 (6)	C4—C6	1.520 (8)
S2—C13	1.709 (7)	C4—H4A	0.9800
S2—C12	1.740 (6)	C5—C7	1.517 (9)
S3—C16	1.702 (8)	C5—H5A	0.9800
S3—C15	1.730 (6)	C6—C8	1.536 (8)
O1—C6	1.446 (6)	C6—H6A	0.9800
O1—C5	1.457 (6)	C7—C8	1.524 (9)
O2—C2	1.268 (6)	C7—H7A	0.9700
O3—C2	1.235 (6)	C7—H7B	0.9700
O4—C1	1.270 (7)	C8—H8A	0.9700
O5—C1	1.233 (7)	C8—H8B	0.9700
N1—C9	1.335 (7)	C10—C11	1.327 (8)
N1—H1A	0.8599	C10—H10A	0.9300
N1—H1B	0.8601	C11—H11A	0.9300
N2—C9	1.332 (7)	C13—C14	1.342 (8)
N2—C11	1.378 (7)	C13—H13A	0.9300
N3—C12	1.325 (7)	C14—H14A	0.9300
N3—H3B	0.8600	C16—C17	1.328 (9)
N3—H3C	0.8600	C16—H16A	0.9300
N4—C12	1.323 (7)	C17—H17A	0.9300
N4—C14	1.385 (7)	O1W—H1	0.855 (19)
N5—C15	1.325 (8)	O1W—H2	0.849 (19)
N5—H5B	0.8600	O2W—H3	0.86 (6)
N5—H5C	0.8601	O2W—H4	0.88 (7)

O4—Cd1—N4	91.47 (16)	C6—C4—H4A	109.4
O4—Cd1—N2	170.80 (16)	C2—C4—H4A	109.4
N4—Cd1—N2	96.67 (17)	C3—C4—H4A	109.4
O4—Cd1—O2	83.02 (15)	O1—C5—C7	101.5 (5)
N4—Cd1—O2	100.56 (15)	O1—C5—C3	102.9 (4)
N2—Cd1—O2	91.26 (16)	C7—C5—C3	110.8 (6)
O4—Cd1—N6	92.84 (16)	O1—C5—H5A	113.5
N4—Cd1—N6	95.89 (18)	C7—C5—H5A	113.5
N2—Cd1—N6	90.59 (17)	C3—C5—H5A	113.5
O2—Cd1—N6	163.12 (16)	O1—C6—C4	103.6 (5)
O4—Cd1—O1	79.80 (14)	O1—C6—C8	101.7 (5)
N4—Cd1—O1	171.27 (14)	C4—C6—C8	110.3 (5)
N2—Cd1—O1	92.05 (14)	O1—C6—H6A	113.4
O2—Cd1—O1	78.69 (13)	C4—C6—H6A	113.4
N6—Cd1—O1	84.48 (15)	C8—C6—H6A	113.4
C9—S1—C10	89.6 (3)	C5—C7—C8	102.5 (5)
C13—S2—C12	89.6 (3)	C5—C7—H7A	111.3
C16—S3—C15	89.0 (4)	C8—C7—H7A	111.3
C6—O1—C5	95.5 (4)	C5—C7—H7B	111.3
C6—O1—Cd1	116.9 (3)	C8—C7—H7B	111.3
C5—O1—Cd1	113.9 (3)	H7A—C7—H7B	109.2
C2—O2—Cd1	127.7 (4)	C7—C8—C6	101.2 (5)
C1—O4—Cd1	126.9 (4)	C7—C8—H8A	111.5
C9—N1—H1A	119.3	C6—C8—H8A	111.5
C9—N1—H1B	120.7	C7—C8—H8B	111.5
H1A—N1—H1B	120.0	C6—C8—H8B	111.5
C9—N2—C11	109.5 (5)	H8A—C8—H8B	109.4
C9—N2—Cd1	130.8 (4)	N2—C9—N1	123.5 (5)
C11—N2—Cd1	119.7 (4)	N2—C9—S1	114.1 (5)
C12—N3—H3B	122.2	N1—C9—S1	122.4 (5)
C12—N3—H3C	117.7	C11—C10—S1	109.4 (5)
H3B—N3—H3C	120.0	C11—C10—H10A	125.3
C12—N4—C14	110.1 (5)	S1—C10—H10A	125.3
C12—N4—Cd1	128.1 (4)	C10—C11—N2	117.4 (6)
C14—N4—Cd1	121.7 (4)	C10—C11—H11A	121.3
C15—N5—H5B	120.1	N2—C11—H11A	121.3
C15—N5—H5C	119.9	N4—C12—N3	125.1 (6)
H5B—N5—H5C	120.0	N4—C12—S2	113.7 (5)
C15—N6—C17	109.2 (6)	N3—C12—S2	121.2 (5)
C15—N6—Cd1	133.1 (4)	C14—C13—S2	110.6 (5)
C17—N6—Cd1	116.9 (4)	C14—C13—H13A	124.7
O5—C1—O4	123.9 (7)	S2—C13—H13A	124.7
O5—C1—C3	118.0 (6)	C13—C14—N4	116.1 (6)
O4—C1—C3	118.1 (6)	C13—C14—H14A	122.0
O3—C2—O2	122.1 (5)	N4—C14—H14A	122.0
O3—C2—C4	118.5 (5)	N6—C15—N5	124.2 (6)
O2—C2—C4	119.4 (5)	N6—C15—S3	114.7 (5)
C1—C3—C5	113.5 (5)	N5—C15—S3	121.0 (5)
C1—C3—C4	116.0 (5)	C17—C16—S3	109.7 (6)
C5—C3—C4	100.6 (5)	C17—C16—H16A	125.1
C1—C3—H3A	108.8	S3—C16—H16A	125.1
C5—C3—H3A	108.8	C16—C17—N6	117.3 (7)
C4—C3—H3A	108.8	C16—C17—H17A	121.3
C6—C4—C2	111.7 (5)	N6—C17—H17A	121.3
C6—C4—C3	100.7 (4)	H1—O1W—H2	104 (3)
C2—C4—C3	116.0 (5)	H3—O2W—H4	103 (10)

O4—Cd1—O1—C6	−96.4 (4)	C1—C3—C4—C6	−122.3 (5)
N2—Cd1—O1—C6	79.4 (4)	C5—C3—C4—C6	0.7 (6)
O2—Cd1—O1—C6	−11.5 (4)	C1—C3—C4—C2	−1.6 (8)
N6—Cd1—O1—C6	169.7 (4)	C5—C3—C4—C2	121.4 (5)
O4—Cd1—O1—C5	13.7 (3)	C6—O1—C5—C7	−57.5 (5)
N2—Cd1—O1—C5	−170.6 (3)	Cd1—O1—C5—C7	179.9 (4)
O2—Cd1—O1—C5	98.5 (3)	C6—O1—C5—C3	57.3 (5)
N6—Cd1—O1—C5	−80.2 (3)	Cd1—O1—C5—C3	−65.4 (5)
O4—Cd1—O2—C2	43.2 (5)	C1—C3—C5—O1	89.2 (6)
N4—Cd1—O2—C2	133.4 (5)	C4—C3—C5—O1	−35.5 (6)
N2—Cd1—O2—C2	−129.6 (5)	C1—C3—C5—C7	−163.0 (5)
N6—Cd1—O2—C2	−33.4 (8)	C4—C3—C5—C7	72.4 (6)
O1—Cd1—O2—C2	−37.7 (5)	C5—O1—C6—C4	−57.1 (5)
N4—Cd1—O4—C1	−139.6 (5)	Cd1—O1—C6—C4	63.2 (5)
O2—Cd1—O4—C1	−39.2 (5)	C5—O1—C6—C8	57.4 (5)
N6—Cd1—O4—C1	124.4 (5)	Cd1—O1—C6—C8	177.8 (3)
O1—Cd1—O4—C1	40.5 (5)	C2—C4—C6—O1	−89.0 (5)
N4—Cd1—N2—C9	103.8 (5)	C3—C4—C6—O1	34.7 (5)
O2—Cd1—N2—C9	3.0 (5)	C2—C4—C6—C8	162.8 (5)
N6—Cd1—N2—C9	−160.3 (5)	C3—C4—C6—C8	−73.5 (6)
O1—Cd1—N2—C9	−75.8 (5)	O1—C5—C7—C8	35.3 (6)
N4—Cd1—N2—C11	−78.4 (4)	C3—C5—C7—C8	−73.4 (6)
O2—Cd1—N2—C11	−179.2 (4)	C5—C7—C8—C6	−0.1 (7)
N6—Cd1—N2—C11	17.6 (4)	O1—C6—C8—C7	−35.5 (6)
O1—Cd1—N2—C11	102.1 (4)	C4—C6—C8—C7	74.0 (6)
O4—Cd1—N4—C12	−1.8 (5)	C11—N2—C9—N1	−179.0 (5)
N2—Cd1—N4—C12	−177.5 (5)	Cd1—N2—C9—N1	−0.9 (9)
O2—Cd1—N4—C12	−85.0 (5)	C11—N2—C9—S1	0.1 (6)
N6—Cd1—N4—C12	91.2 (5)	Cd1—N2—C9—S1	178.1 (3)
O4—Cd1—N4—C14	173.2 (4)	C10—S1—C9—N2	−0.6 (5)
N2—Cd1—N4—C14	−2.5 (4)	C10—S1—C9—N1	178.4 (5)
O2—Cd1—N4—C14	90.0 (4)	C9—S1—C10—C11	1.0 (5)
N6—Cd1—N4—C14	−93.8 (4)	S1—C10—C11—N2	−1.2 (7)
O4—Cd1—N6—C15	−109.7 (5)	C9—N2—C11—C10	0.7 (8)
N4—Cd1—N6—C15	158.5 (5)	Cd1—N2—C11—C10	−177.5 (4)
N2—Cd1—N6—C15	61.7 (6)	C14—N4—C12—N3	179.4 (6)
O2—Cd1—N6—C15	−34.5 (9)	Cd1—N4—C12—N3	−5.1 (9)
O1—Cd1—N6—C15	−30.3 (5)	C14—N4—C12—S2	0.2 (7)
O4—Cd1—N6—C17	81.7 (4)	Cd1—N4—C12—S2	175.7 (2)
N4—Cd1—N6—C17	−10.0 (5)	C13—S2—C12—N4	−0.8 (5)
N2—Cd1—N6—C17	−106.8 (4)	C13—S2—C12—N3	−180.0 (5)
O2—Cd1—N6—C17	156.9 (5)	C12—S2—C13—C14	1.1 (5)
O1—Cd1—N6—C17	161.2 (4)	S2—C13—C14—N4	−1.2 (7)
Cd1—O4—C1—O5	144.3 (5)	C12—N4—C14—C13	0.6 (8)
Cd1—O4—C1—C3	−35.5 (8)	Cd1—N4—C14—C13	−175.2 (4)
Cd1—O2—C2—O3	−154.3 (4)	C17—N6—C15—N5	178.0 (6)
Cd1—O2—C2—C4	28.5 (8)	Cd1—N6—C15—N5	8.8 (10)
O5—C1—C3—C5	145.8 (6)	C17—N6—C15—S3	0.1 (7)
O4—C1—C3—C5	−34.4 (7)	Cd1—N6—C15—S3	−169.1 (3)
O5—C1—C3—C4	−98.4 (7)	C16—S3—C15—N6	0.6 (5)
O4—C1—C3—C4	81.4 (7)	C16—S3—C15—N5	−177.3 (6)
O3—C2—C4—C6	−137.0 (6)	C15—S3—C16—C17	−1.2 (6)
O2—C2—C4—C6	40.3 (7)	S3—C16—C17—N6	1.5 (8)
O3—C2—C4—C3	108.4 (6)	C15—N6—C17—C16	−1.1 (9)
O2—C2—C4—C3	−74.4 (7)	Cd1—N6—C17—C16	170.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.04	2.867 (6)	161
N1—H1B···O3ⁱ	0.86	2.19	2.931 (6)	144
N3—H3B···O4	0.86	2.00	2.803 (7)	156
N3—H3C···O1Wⁱⁱ	0.86	2.14	2.965 (7)	160
N5—H5B···O1	0.86	2.15	2.917 (7)	149
N5—H5C···O3ⁱⁱⁱ	0.86	2.46	3.177 (7)	141
N5—H5C···O2W^iv	0.86	2.47	3.052 (9)	125
O1W—H1···O5^v	0.86 (2)	1.97 (2)	2.817 (6)	174 (7)
O1W—H2···O3^vi	0.85 (2)	2.03 (2)	2.865 (6)	168 (6)
O2W—H3···O5^vii	0.86 (6)	2.25 (6)	2.996 (9)	145 (9)
O2W—H4···O5	0.88 (7)	2.12 (4)	2.962 (10)	162 (12)

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

Experimental details

Crystal data
Chemical formula	[Cd(C₈H₈O₅)(C₃H₄N₂S)₃]·2H₂O
M_r	633.00
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.6457 (3), 9.9255 (3), 25.4653 (9)
β (°)	101.980 (2)
V (Å³)	2384.91 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.08 × 0.08 × 0.04

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.90, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	19757, 5480, 2777
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.119, 1.01
No. of reflections	5480
No. of parameters	319
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.69

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—O4	2.268 (4)	Cd1—O2	2.312 (4)
Cd1—N4	2.302 (5)	Cd1—N6	2.341 (5)
Cd1—N2	2.305 (5)	Cd1—O1	2.467 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.04	2.867 (6)	161.1
N1—H1B···O3ⁱ	0.86	2.19	2.931 (6)	143.9
N3—H3B···O4	0.86	2.00	2.803 (7)	155.7
N3—H3C···O1Wⁱⁱ	0.86	2.14	2.965 (7)	160.1
N5—H5B···O1	0.86	2.15	2.917 (7)	148.6
N5—H5C···O3ⁱⁱⁱ	0.86	2.46	3.177 (7)	141.0
N5—H5C···O2W^iv	0.86	2.47	3.052 (9)	125.3
O1W—H1···O5^v	0.855 (19)	1.97 (2)	2.817 (6)	174 (7)
O1W—H2···O3^vi	0.849 (19)	2.03 (2)	2.865 (6)	168 (6)
O2W—H3···O5^vii	0.86 (6)	2.25 (6)	2.996 (9)	145 (9)
O2W—H4···O5	0.88 (7)	2.12 (4)	2.962 (10)	162 (12)

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

Acknowledgements

The authors are grateful for financial support from the Natural Science Foundation of Zhejiang Province, China (grant No. Y407301).

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Shimi, I. R., Zaki, Z., Shoukry, S. & Medhat, A. M. (1982). Eur. J. Cancer Clin. Oncol. 18, 785–789. CrossRef CAS PubMed Web of Science Google Scholar
Yin, F. L., Shen, J., Zou, J. J. & Li, R. C. (2003). Acta Chim. Sin. 61, 556–561. 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.