Bis(2-amino-1,3-benzothia­zol-3-ium) bis­(7-oxabicyclo­[2.2.1]heptane-2,3-dicarboxyl­ato)cadmate hexa­hydrate

Zhang, F.; Lin, Q.-Y.; Chen, L.-L.; Ke, J.-G.

doi:10.1107/S1600536812022593

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m818

doi:10.1107/S1600536812022593

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Bis(2-amino-1,3-benzothiazol-3-ium) bis(7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylato)cadmate hexahydrate

Fan Zhang,^a,^b Qiu-Yue Lin,^a,^b ^* Ling-Ling Chen ^b and Jun-Gang Ke ^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, and ^bCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
^*Correspondence e-mail: sky51@zjnu.cn

(Received 10 May 2012; accepted 17 May 2012; online 26 May 2012)

In the structure of the title complex, (C₇H₇N₂S)₂[Cd(C₈H₈O₅)₂]·6H₂O, the Cd^II atom is located on an inversion center and is O,O′,O′′-chelated by two symmetry-related 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylate ligands in a distorted octahedral geometry. The 2-aminobenzothiazolium cation links with the Cd complex anion via N—H⋯O hydrogen bonding. Extensive O—H⋯O and N—H⋯O hydrogen bonds involving lattice water molecules occur in the crystal structure.

Related literature

For background to the applications of 7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylic anhydride (norcantharidin), see: Yin et al. (2005 ). For a manganese(II) analogue, see: Wang et al. (2010a ), for a cobalt(II) analogue, see: Wang et al. (2010b ), for a nickel(II) analogue, see: Wang et al. (2012 ) and for a zinc(II) analogue, see: Zhang et al. (2012 ).

Experimental

Crystal data

(C₇H₇N₂S)₂[Cd(C₈H₈O₅)₂]·6H₂O
M_r = 891.23
Triclinic, $[P \overline 1]$
a = 6.6990 (8) Å
b = 10.3103 (10) Å
c = 13.0979 (13) Å
α = 89.039 (7)°
β = 89.004 (7)°
γ = 82.062 (7)°
V = 895.76 (16) Å³
Z = 1
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 296 K
0.12 × 0.08 × 0.06 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.927, T_max = 0.957
12401 measured reflections
3138 independent reflections
2782 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.070
S = 1.07
3138 reflections
250 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—O1	2.2108 (18)
Cd1—O3	2.2954 (18)
Cd1—O5	2.3499 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2	0.85	1.85	2.682 (3)	167
O2W—H2WB⋯O3W	0.85	2.15	2.995 (3)	170
O1W—H1WB⋯O3W	0.85	1.96	2.806 (3)	173
O3W—H3WB⋯O4	0.85	2.02	2.837 (3)	161
N1—H1A⋯O4ⁱ	0.86	1.84	2.700 (3)	176
N2—H2A⋯O3ⁱ	0.86	2.00	2.845 (3)	169
N2—H2B⋯O1Wⁱⁱ	0.86	2.00	2.824 (3)	160
O2W—H2WA⋯O1Wⁱⁱ	0.85	1.93	2.758 (4)	164
O3W—H3WA⋯O2Wⁱⁱⁱ	0.85	1.96	2.794 (3)	166
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1.

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: 10.1107/S1600536812022593/vn2038sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022593/vn2038Isup2.hkl

checkCIF report

Comment top

7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylic anhydride (norcantharidin), which possesses great anti-cancer activity, has been used in clinic tests (Yin et al., 2005). An isostructural norcantharadin manganese complex (Wang et al., 2010a), a cobalt complex (Wang et al., 2010b), a nickel complex (Wang et al.,2012) and a zinc complex (Zhang et al., 2012) have been reported. The molecular structure of the title complex is shown in Fig.1. The cadmium atom is six-coordinated in a distorted octahedral coordination mode, binding to two bridging O atoms of the bicycloheptane unit and four carboxylate O atoms of two symmetry-related and fully deprotonated ligands. 2-aminobenzothiazole is not involved in the coordination of the cation, and N atom of thiazole ring is protonated.The crystal structure is stabilized by N—H···O hydrogen-bonding interactions between the cations and anions and O—H···O hydrogen bonds including the crystal water molecules.

Related literature top

For background to the applications of 7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylic anhydride (norcantharidin), see: Yin et al. (2005). For a manganese(II) analogue, see: Wang et al. (2010a), for a cobalt(II) analogue, see: Wang et al. (2010b), for a nickel(II) analogue, see: Wang et al. (2012) and for a zinc(II) analogue, see: Zhang et al. (2012).

Experimental top

A mixture of 0.5 mmol norcantharidin, 0.5 mmol cadmium acetate, 0.5 mmol 2-aminobenzothiazole and 15 mL distilled water was sealed in a 25 mL Teflon-lined stainless vessel and heated at 443 K for 3 d, then slowly cooled to room temperature. The solution was filtered and block-shaped colorless crystals were obtained.

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 (I) showing the atom-labelling scheme with displacement ellipsoids drawn at the 30% probability.

Bis(2-amino-1,3-benzothiazol-3-ium) bis(7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylato)cadmate hexahydrate top

Crystal data top

(C₇H₇N₂S)₂[Cd(C₈H₈O₅)₂]·6H₂O	Z = 1
M_r = 891.23	F(000) = 458
Triclinic, P1	D_x = 1.652 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6990 (8) Å	Cell parameters from 3684 reflections
b = 10.3103 (10) Å	θ = 1.6–25.0°
c = 13.0979 (13) Å	µ = 0.81 mm⁻¹
α = 89.039 (7)°	T = 296 K
β = 89.004 (7)°	Block, colourless
γ = 82.062 (7)°	0.12 × 0.08 × 0.06 mm
V = 895.76 (16) Å³

Data collection top

Bruker APEXII area-detector diffractometer	3138 independent reflections
Radiation source: fine-focus sealed tube	2782 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.927, T_max = 0.957	k = −12→12
12401 measured reflections	l = −15→15

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0329P)² + 0.3371P] where P = (F_o² + 2F_c²)/3
3138 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

(C₇H₇N₂S)₂[Cd(C₈H₈O₅)₂]·6H₂O	γ = 82.062 (7)°
M_r = 891.23	V = 895.76 (16) Å³
Triclinic, P1	Z = 1
a = 6.6990 (8) Å	Mo Kα radiation
b = 10.3103 (10) Å	µ = 0.81 mm⁻¹
c = 13.0979 (13) Å	T = 296 K
α = 89.039 (7)°	0.12 × 0.08 × 0.06 mm
β = 89.004 (7)°

Data collection top

Bruker APEXII area-detector diffractometer	3138 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2782 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.957	R_int = 0.037
12401 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.07	Δρ_max = 0.39 e Å⁻³
3138 reflections	Δρ_min = −0.33 e Å⁻³
250 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 > 2sigma(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	0.5000	0.0000	0.0000	0.02740 (11)
S1	0.67420 (11)	0.26053 (7)	0.52095 (5)	0.03489 (19)
N1	0.7260 (3)	0.0299 (2)	0.59906 (16)	0.0269 (5)
H1A	0.7363	−0.0334	0.6431	0.032*
N2	0.6614 (4)	0.1938 (2)	0.71990 (17)	0.0357 (6)
H2A	0.6700	0.1374	0.7693	0.043*
H2B	0.6361	0.2761	0.7325	0.043*
O1	0.6235 (3)	0.16660 (17)	0.06762 (15)	0.0342 (5)
O1W	0.4780 (4)	0.5348 (2)	0.28331 (18)	0.0480 (6)
H1WA	0.5186	0.4890	0.2317	0.072*
H1WB	0.3871	0.4986	0.3141	0.072*
O2	0.6139 (3)	0.35871 (19)	0.14105 (15)	0.0394 (5)
O2W	0.1911 (4)	0.4499 (3)	0.59727 (19)	0.0624 (7)
H2WA	0.3036	0.4588	0.6234	0.094*
H2WB	0.2054	0.4335	0.5340	0.094*
O3	0.2779 (3)	0.01702 (17)	0.13613 (13)	0.0333 (5)
O3W	0.1839 (4)	0.3984 (2)	0.37312 (18)	0.0552 (6)
H3WA	0.0724	0.4490	0.3713	0.083*
H3WB	0.1880	0.3405	0.3274	0.083*
O4	0.2247 (3)	0.16445 (18)	0.25914 (14)	0.0342 (5)
O5	0.2679 (3)	0.16742 (17)	−0.07122 (13)	0.0297 (4)
C6	0.1262 (4)	0.3800 (3)	−0.1106 (2)	0.0329 (6)
H6A	0.1338	0.3824	−0.1846	0.039*
H6B	0.1048	0.4688	−0.0854	0.039*
C5	−0.0403 (4)	0.3011 (3)	−0.0718 (2)	0.0348 (7)
H5A	−0.1379	0.3537	−0.0286	0.042*
H5B	−0.1095	0.2677	−0.1280	0.042*
C1	0.3151 (4)	0.3013 (2)	−0.06518 (19)	0.0268 (6)
H1B	0.4400	0.3149	−0.1013	0.032*
C4	0.0804 (4)	0.1902 (3)	−0.0110 (2)	0.0290 (6)
H4A	0.0123	0.1123	−0.0029	0.035*
C2	0.3217 (4)	0.3217 (2)	0.05110 (19)	0.0236 (6)
H2C	0.2807	0.4145	0.0659	0.028*
C3	0.1510 (4)	0.2401 (2)	0.08993 (19)	0.0240 (6)
H3A	0.0406	0.2998	0.1206	0.029*
C7	0.5339 (4)	0.2791 (3)	0.0913 (2)	0.0264 (6)
C8	0.2237 (4)	0.1329 (3)	0.1673 (2)	0.0266 (6)
C9	0.7242 (4)	0.1270 (3)	0.4387 (2)	0.0300 (6)
C10	0.7405 (4)	0.1277 (3)	0.3330 (2)	0.0395 (7)
H10A	0.7240	0.2058	0.2956	0.047*
C11	0.7818 (5)	0.0087 (3)	0.2852 (2)	0.0451 (8)
H11A	0.7938	0.0065	0.2144	0.054*
C12	0.8059 (4)	−0.1076 (3)	0.3408 (2)	0.0408 (7)
H12A	0.8337	−0.1865	0.3065	0.049*
C13	0.7897 (4)	−0.1093 (3)	0.4460 (2)	0.0327 (6)
H13A	0.8053	−0.1876	0.4831	0.039*
C14	0.7494 (4)	0.0096 (3)	0.49408 (19)	0.0257 (6)
C15	0.6867 (4)	0.1544 (3)	0.6253 (2)	0.0269 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.03353 (18)	0.01935 (16)	0.02779 (17)	0.00173 (11)	0.00364 (12)	−0.00422 (11)
S1	0.0462 (5)	0.0268 (4)	0.0307 (4)	−0.0022 (3)	−0.0007 (3)	0.0056 (3)
N1	0.0304 (13)	0.0259 (12)	0.0248 (12)	−0.0054 (9)	−0.0008 (9)	0.0044 (9)
N2	0.0538 (16)	0.0271 (13)	0.0257 (12)	−0.0046 (11)	0.0014 (11)	−0.0006 (10)
O1	0.0308 (11)	0.0251 (10)	0.0456 (12)	0.0010 (8)	−0.0048 (9)	−0.0076 (9)
O1W	0.0570 (16)	0.0340 (12)	0.0522 (14)	−0.0043 (10)	0.0143 (11)	−0.0108 (10)
O2	0.0370 (12)	0.0364 (12)	0.0467 (12)	−0.0089 (9)	−0.0047 (9)	−0.0161 (10)
O2W	0.0599 (16)	0.0736 (18)	0.0512 (15)	0.0011 (14)	−0.0085 (12)	−0.0075 (14)
O3	0.0461 (12)	0.0223 (10)	0.0289 (10)	0.0031 (8)	0.0099 (9)	0.0026 (8)
O3W	0.0620 (16)	0.0484 (15)	0.0533 (15)	−0.0003 (12)	0.0115 (12)	−0.0161 (12)
O4	0.0501 (13)	0.0284 (10)	0.0235 (10)	−0.0034 (9)	0.0028 (9)	0.0002 (8)
O5	0.0389 (11)	0.0233 (10)	0.0255 (10)	0.0012 (8)	−0.0019 (8)	−0.0045 (8)
C6	0.0436 (18)	0.0274 (15)	0.0262 (14)	0.0003 (12)	−0.0045 (12)	0.0035 (12)
C5	0.0343 (17)	0.0332 (16)	0.0357 (16)	0.0002 (12)	−0.0086 (13)	−0.0007 (13)
C1	0.0333 (15)	0.0227 (14)	0.0240 (14)	−0.0036 (11)	0.0058 (11)	0.0021 (11)
C4	0.0282 (15)	0.0226 (14)	0.0364 (16)	−0.0041 (11)	−0.0021 (12)	−0.0001 (12)
C2	0.0302 (15)	0.0151 (13)	0.0250 (13)	−0.0004 (10)	0.0003 (11)	−0.0035 (10)
C3	0.0250 (14)	0.0203 (13)	0.0254 (13)	0.0009 (10)	0.0052 (11)	−0.0013 (11)
C7	0.0310 (15)	0.0238 (15)	0.0251 (14)	−0.0066 (12)	0.0041 (11)	−0.0012 (11)
C8	0.0243 (14)	0.0258 (15)	0.0295 (15)	−0.0040 (11)	0.0086 (11)	0.0030 (12)
C9	0.0268 (15)	0.0329 (16)	0.0302 (15)	−0.0037 (12)	−0.0033 (11)	0.0037 (12)
C10	0.0404 (18)	0.052 (2)	0.0262 (15)	−0.0056 (14)	−0.0030 (13)	0.0081 (14)
C11	0.0399 (19)	0.072 (2)	0.0240 (15)	−0.0108 (16)	0.0002 (13)	−0.0062 (16)
C12	0.0357 (17)	0.0481 (19)	0.0387 (18)	−0.0045 (14)	0.0006 (13)	−0.0152 (15)
C13	0.0289 (16)	0.0330 (16)	0.0367 (16)	−0.0048 (12)	−0.0021 (12)	−0.0043 (13)
C14	0.0188 (14)	0.0331 (15)	0.0253 (14)	−0.0034 (11)	−0.0022 (10)	−0.0004 (12)
C15	0.0273 (15)	0.0267 (15)	0.0270 (14)	−0.0046 (11)	−0.0025 (11)	0.0020 (12)

Geometric parameters (Å, º) top

Cd1—O1ⁱ	2.2108 (18)	C6—C1	1.530 (4)
Cd1—O1	2.2108 (18)	C6—C5	1.543 (4)
Cd1—O3	2.2954 (18)	C6—H6A	0.9700
Cd1—O3ⁱ	2.2954 (18)	C6—H6B	0.9700
Cd1—O5ⁱ	2.3499 (17)	C5—C4	1.527 (4)
Cd1—O5	2.3499 (17)	C5—H5A	0.9700
S1—C15	1.733 (3)	C5—H5B	0.9700
S1—C9	1.754 (3)	C1—C2	1.543 (3)
N1—C15	1.324 (3)	C1—H1B	0.9800
N1—C14	1.397 (3)	C4—C3	1.532 (4)
N1—H1A	0.8600	C4—H4A	0.9800
N2—C15	1.311 (3)	C2—C7	1.528 (4)
N2—H2A	0.8600	C2—C3	1.583 (3)
N2—H2B	0.8600	C2—H2C	0.9800
O1—C7	1.271 (3)	C3—C8	1.522 (3)
O1W—H1WA	0.8501	C3—H3A	0.9800
O1W—H1WB	0.8500	C9—C10	1.388 (4)
O2—C7	1.240 (3)	C9—C14	1.391 (4)
O2W—H2WA	0.8499	C10—C11	1.378 (4)
O2W—H2WB	0.8500	C10—H10A	0.9300
O3—C8	1.271 (3)	C11—C12	1.384 (4)
O3W—H3WA	0.8500	C11—H11A	0.9300
O3W—H3WB	0.8500	C12—C13	1.381 (4)
O4—C8	1.252 (3)	C12—H12A	0.9300
O5—C1	1.461 (3)	C13—C14	1.378 (4)
O5—C4	1.464 (3)	C13—H13A	0.9300

O1ⁱ—Cd1—O1	180.00 (10)	C2—C1—H1B	113.6
O1ⁱ—Cd1—O3	94.23 (7)	O5—C4—C5	101.6 (2)
O1—Cd1—O3	85.77 (7)	O5—C4—C3	102.5 (2)
O1ⁱ—Cd1—O3ⁱ	85.77 (7)	C5—C4—C3	110.9 (2)
O1—Cd1—O3ⁱ	94.23 (7)	O5—C4—H4A	113.6
O3—Cd1—O3ⁱ	180.00 (6)	C5—C4—H4A	113.6
O1ⁱ—Cd1—O5ⁱ	82.90 (6)	C3—C4—H4A	113.6
O1—Cd1—O5ⁱ	97.10 (6)	C7—C2—C1	110.9 (2)
O3—Cd1—O5ⁱ	96.23 (6)	C7—C2—C3	116.9 (2)
O3ⁱ—Cd1—O5ⁱ	83.77 (6)	C1—C2—C3	100.8 (2)
O1ⁱ—Cd1—O5	97.10 (6)	C7—C2—H2C	109.3
O1—Cd1—O5	82.90 (6)	C1—C2—H2C	109.3
O3—Cd1—O5	83.77 (6)	C3—C2—H2C	109.3
O3ⁱ—Cd1—O5	96.23 (6)	C8—C3—C4	114.5 (2)
O5ⁱ—Cd1—O5	180.00 (8)	C8—C3—C2	113.7 (2)
C15—S1—C9	90.15 (13)	C4—C3—C2	101.3 (2)
C15—N1—C14	114.6 (2)	C8—C3—H3A	109.0
C15—N1—H1A	122.7	C4—C3—H3A	109.0
C14—N1—H1A	122.7	C2—C3—H3A	109.0
C15—N2—H2A	120.0	O2—C7—O1	123.2 (3)
C15—N2—H2B	120.0	O2—C7—C2	118.2 (2)
H2A—N2—H2B	120.0	O1—C7—C2	118.5 (2)
C7—O1—Cd1	129.36 (17)	O4—C8—O3	123.6 (2)
H1WA—O1W—H1WB	108.2	O4—C8—C3	117.4 (2)
H2WA—O2W—H2WB	110.7	O3—C8—C3	119.0 (2)
C8—O3—Cd1	115.11 (15)	C10—C9—C14	120.7 (3)
H3WA—O3W—H3WB	110.4	C10—C9—S1	128.6 (2)
C1—O5—C4	95.87 (18)	C14—C9—S1	110.64 (19)
C1—O5—Cd1	117.20 (15)	C11—C10—C9	117.7 (3)
C4—O5—Cd1	112.02 (14)	C11—C10—H10A	121.1
C1—C6—C5	101.8 (2)	C9—C10—H10A	121.1
C1—C6—H6A	111.4	C10—C11—C12	121.2 (3)
C5—C6—H6A	111.4	C10—C11—H11A	119.4
C1—C6—H6B	111.4	C12—C11—H11A	119.4
C5—C6—H6B	111.4	C13—C12—C11	121.5 (3)
H6A—C6—H6B	109.3	C13—C12—H12A	119.3
C4—C5—C6	102.0 (2)	C11—C12—H12A	119.3
C4—C5—H5A	111.4	C14—C13—C12	117.5 (3)
C6—C5—H5A	111.4	C14—C13—H13A	121.2
C4—C5—H5B	111.4	C12—C13—H13A	121.2
C6—C5—H5B	111.4	C13—C14—C9	121.4 (2)
H5A—C5—H5B	109.2	C13—C14—N1	126.8 (2)
O5—C1—C6	101.6 (2)	C9—C14—N1	111.9 (2)
O5—C1—C2	102.46 (18)	N2—C15—N1	124.0 (2)
C6—C1—C2	110.8 (2)	N2—C15—S1	123.3 (2)
O5—C1—H1B	113.6	N1—C15—S1	112.69 (19)
C6—C1—H1B	113.6

O3—Cd1—O1—C7	−55.7 (2)	C5—C4—C3—C2	−72.4 (2)
O3ⁱ—Cd1—O1—C7	124.3 (2)	C7—C2—C3—C8	2.8 (3)
O5ⁱ—Cd1—O1—C7	−151.4 (2)	C1—C2—C3—C8	123.0 (2)
O5—Cd1—O1—C7	28.6 (2)	C7—C2—C3—C4	−120.5 (2)
O1ⁱ—Cd1—O3—C8	−146.03 (18)	C1—C2—C3—C4	−0.3 (2)
O1—Cd1—O3—C8	33.97 (18)	Cd1—O1—C7—O2	170.25 (19)
O5ⁱ—Cd1—O3—C8	130.68 (18)	Cd1—O1—C7—C2	−13.6 (3)
O5—Cd1—O3—C8	−49.32 (18)	C1—C2—C7—O2	126.0 (2)
O1ⁱ—Cd1—O5—C1	−167.19 (16)	C3—C2—C7—O2	−119.3 (3)
O1—Cd1—O5—C1	12.81 (16)	C1—C2—C7—O1	−50.4 (3)
O3—Cd1—O5—C1	99.31 (16)	C3—C2—C7—O1	64.3 (3)
O3ⁱ—Cd1—O5—C1	−80.69 (16)	Cd1—O3—C8—O4	−131.4 (2)
O1ⁱ—Cd1—O5—C4	83.43 (16)	Cd1—O3—C8—C3	49.3 (3)
O1—Cd1—O5—C4	−96.57 (16)	C4—C3—C8—O4	−158.7 (2)
O3—Cd1—O5—C4	−10.07 (15)	C2—C3—C8—O4	85.5 (3)
O3ⁱ—Cd1—O5—C4	169.93 (15)	C4—C3—C8—O3	20.6 (3)
C1—C6—C5—C4	−0.2 (3)	C2—C3—C8—O3	−95.1 (3)
C4—O5—C1—C6	−57.3 (2)	C15—S1—C9—C10	179.8 (3)
Cd1—O5—C1—C6	−175.78 (14)	C15—S1—C9—C14	−0.5 (2)
C4—O5—C1—C2	57.3 (2)	C14—C9—C10—C11	0.1 (4)
Cd1—O5—C1—C2	−61.1 (2)	S1—C9—C10—C11	179.8 (2)
C5—C6—C1—O5	35.4 (2)	C9—C10—C11—C12	0.2 (5)
C5—C6—C1—C2	−72.9 (3)	C10—C11—C12—C13	0.0 (5)
C1—O5—C4—C5	57.2 (2)	C11—C12—C13—C14	−0.3 (4)
Cd1—O5—C4—C5	179.65 (15)	C12—C13—C14—C9	0.6 (4)
C1—O5—C4—C3	−57.6 (2)	C12—C13—C14—N1	179.6 (2)
Cd1—O5—C4—C3	64.89 (19)	C10—C9—C14—C13	−0.5 (4)
C6—C5—C4—O5	−34.9 (3)	S1—C9—C14—C13	179.8 (2)
C6—C5—C4—C3	73.4 (3)	C10—C9—C14—N1	−179.6 (2)
O5—C1—C2—C7	89.5 (2)	S1—C9—C14—N1	0.7 (3)
C6—C1—C2—C7	−162.8 (2)	C15—N1—C14—C13	−179.6 (3)
O5—C1—C2—C3	−34.9 (2)	C15—N1—C14—C9	−0.5 (3)
C6—C1—C2—C3	72.8 (2)	C14—N1—C15—N2	−179.4 (2)
O5—C4—C3—C8	−87.4 (2)	C14—N1—C15—S1	0.1 (3)
C5—C4—C3—C8	164.8 (2)	C9—S1—C15—N2	179.7 (2)
O5—C4—C3—C2	35.3 (2)	C9—S1—C15—N1	0.2 (2)

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
O1W—H1WA···O2	0.85	1.85	2.682 (3)	167
O2W—H2WB···O3W	0.85	2.15	2.995 (3)	170
O1W—H1WB···O3W	0.85	1.96	2.806 (3)	173
O3W—H3WB···O4	0.85	2.02	2.837 (3)	161
N1—H1A···O4ⁱⁱ	0.86	1.84	2.700 (3)	176
N2—H2A···O3ⁱⁱ	0.86	2.00	2.845 (3)	169
N2—H2B···O1Wⁱⁱⁱ	0.86	2.00	2.824 (3)	160
O2W—H2WA···O1Wⁱⁱⁱ	0.85	1.93	2.758 (4)	164
O3W—H3WA···O2W^iv	0.85	1.96	2.794 (3)	166

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

Experimental details

Crystal data
Chemical formula	(C₇H₇N₂S)₂[Cd(C₈H₈O₅)₂]·6H₂O
M_r	891.23
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.6990 (8), 10.3103 (10), 13.0979 (13)
α, β, γ (°)	89.039 (7), 89.004 (7), 82.062 (7)
V (Å³)	895.76 (16)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.12 × 0.08 × 0.06

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.927, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	12401, 3138, 2782
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.070, 1.07
No. of reflections	3138
No. of parameters	250
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.33

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

Selected bond lengths (Å) top

Cd1—O1	2.2108 (18)	Cd1—O5	2.3499 (17)
Cd1—O3	2.2954 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2	0.85	1.85	2.682 (3)	167.0
O2W—H2WB···O3W	0.85	2.15	2.995 (3)	169.8
O1W—H1WB···O3W	0.85	1.96	2.806 (3)	173.2
O3W—H3WB···O4	0.85	2.02	2.837 (3)	161.0
N1—H1A···O4ⁱ	0.86	1.84	2.700 (3)	175.7
N2—H2A···O3ⁱ	0.86	2.00	2.845 (3)	168.5
N2—H2B···O1Wⁱⁱ	0.86	2.00	2.824 (3)	159.7
O2W—H2WA···O1Wⁱⁱ	0.85	1.93	2.758 (4)	164.1
O3W—H3WA···O2Wⁱⁱⁱ	0.85	1.96	2.794 (3)	165.5

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

Acknowledgements

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

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
Wang, N., Lin, Q.-Y., Feng, J., Li, S.-K. & Zhao, J.-J. (2010b). Acta Cryst. E66, m763–m764. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, N., Wen, Y.-H., Lin, Q.-Y. & Feng, J. (2010a). Acta Cryst. E66, m762. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, G.-X., Zhang, Q.-W. & Zhang, F. (2012). Acta Cryst. E68, m683. CSD CrossRef IUCr Journals Google Scholar
Yin, F.-L., Zou, J.-J., Xu, L., Wang, X. & Li, R.-C. (2005). J. Rare Earths, 23, 596–599. Google Scholar
Zhang, F., Lv, T.-X., Feng, J. & Lin, Q.-Y. (2012). Acta Cryst. E68, m684. CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page m818

doi:10.1107/S1600536812022593

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis(2-amino-1,3-benzo­thia­zol-3-ium) bis­­(7-oxabi­cyclo­[2.2.1]heptane-2,3-di­carboxyl­ato)cadmate hexa­hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(2-amino-1,3-benzothiazol-3-ium) bis(7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylato)cadmate hexahydrate