catena-Poly[[(tetra­aqua­cadmium)-μ-4,4′-bipyridine-κ2N:N′] 4-hy­droxy-3-sulfonato­benzoate monohydrate]

Gao, S.; Ng, S.W.

doi:10.1107/S1600536812018727

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m715

doi:10.1107/S1600536812018727

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catena-Poly[[(tetraaquacadmium)-μ-4,4′-bipyridine-κ²N:N′] 4-hydroxy-3-sulfonatobenzoate monohydrate]

Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 23 April 2012; accepted 26 April 2012; online 2 May 2012)

The two independent Cd^II atoms in the polymeric title compound, [Cd(C₁₀H₈N₂)(H₂O)₄](C₇H₄O₆S)·H₂O, lie on twofold rotation axes, and each is coordinated by four water molecules and the N atoms of two 4,4′-bipyridine molecules in an octahedral geometry. Bridging gives rise to chains along [101] and [-101]. The 4-hydroxy-3-sulfonatobenzoate dianions are not connected to the Cd^II atoms, but form hydrogen bonds to the coordinated water molecules as well as the lattice water molecule, generating a three-dimensional network.

Related literature

For the 1,10-phenanthroline-chelated Mn^II derivative of 4-hydroxy-3-sulfonatobenzoic acid, see: Fang et al. (2011 ).

Experimental

Crystal data

[Cd(C₁₀H₈N₂)(H₂O)₄](C₇H₄O₆S)·H₂O
M_r = 574.83
Orthorhombic, P b c n
a = 16.3246 (10) Å
b = 15.3063 (11) Å
c = 16.5084 (10) Å
V = 4124.9 (5) Å³
Z = 8
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 293 K
0.18 × 0.16 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.810, T_max = 0.867
61947 measured reflections
4705 independent reflections
3503 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.090
S = 1.04
4705 reflections
334 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.87 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O5ⁱ	0.84 (1)	1.93 (1)	2.762 (4)	171 (5)
O1w—H12⋯O1	0.84 (1)	1.99 (2)	2.805 (3)	163 (5)
O2w—H21⋯O6ⁱⁱ	0.84 (1)	2.36 (2)	3.136 (3)	154 (4)
O2w—H22⋯O5wⁱⁱ	0.84 (1)	1.85 (1)	2.685 (4)	173 (5)
O3w—H31⋯O2ⁱⁱⁱ	0.84 (1)	2.08 (2)	2.858 (3)	155 (3)
O3w—H32⋯O6^iv	0.84 (1)	1.99 (1)	2.812 (3)	167 (4)
O4w—H41⋯O1^v	0.84 (1)	1.84 (1)	2.675 (3)	178 (4)
O4w—H42⋯O4^vi	0.84 (1)	2.10 (2)	2.869 (3)	154 (4)
O5w—H51⋯O2	0.84 (1)	1.96 (2)	2.779 (3)	166 (5)
O5w—H52⋯O6^vii	0.84 (1)	2.06 (2)	2.850 (4)	157 (6)
O3—H3⋯O2^viii	0.84 (1)	1.91 (1)	2.746 (3)	176 (4)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z+1]$ ; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (vi) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (vii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (viii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018727/bt5895sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018727/bt5895Isup2.hkl

checkCIF report

Comment top

The doubly-deprotonated 4-hydroxy-3-sulfonatobenzoic acid ion functions in a chelating mode to connect Mn^II atoms into a chain motif. In this coordination polymer, the metal atom is chelated by 1,10-phenanthroline. When the N-heterocycle is replaced by 4,4'-bipyridine in the present synthesis (and with Cd replacing Mn), the dianion is now connected only indirectly, in an outer-sphere type of coordination. The two independent Cd atoms in polymeric [Cd(H₂O)₄(C₁₀H₈N₂)]^2+.(C₇H₄O₆S)^2–.H₂O lie on twofold rotation axes, and each is coordinated by four water molecules and the N atoms of two 4,4'-bipyridine molecules in an octahedral geometry (Fig. 1). µ-Bridging gives rise to a chain along [-1 0 1]. The C₇H₄O₆S^2– dianion interacts indirectly through the coordinated water molecules as well as through the lattice water molecule to generate a three-dimensional network (Table 1).

Related literature top

For the 1,10-phenanthroline-chelated Mn^II derivative of 4-hydroxy-3-sulfonatobenzoic acid, see: Fang et al. (2011).

Experimental top

A methanol solution (5 ml) of 4,4'-bipyridine (1 mmol) was added to an aqueous solution (10 ml) of cadium(II) dichloride (1 mmol), 2-hydroxy-5-carboxybenzenesulfonic acid (2 mmol) and lithium hydroxide (4 mmol). Colorless crystals were isolated from the solution after several days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of a portion of the structure of polymeric [Cd(H₂O)₄(C₁₀H₈N₂)]^2+.(C₇H₄O₆S)^2–.H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

catena-Poly[[(tetraaquacadmium)-µ-4,4'-bipyridine- κ²N:N'] 4-hydroxy-3-sulfonatobenzoate monohydrate] top

Crystal data top

[Cd(C₁₀H₈N₂)(H₂O)₄](C₇H₄O₆S)·H₂O	F(000) = 2320
M_r = 574.83	D_x = 1.851 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 29441 reflections
a = 16.3246 (10) Å	θ = 3.1–27.5°
b = 15.3063 (11) Å	µ = 1.23 mm⁻¹
c = 16.5084 (10) Å	T = 293 K
V = 4124.9 (5) Å³	Prism, colorless
Z = 8	0.18 × 0.16 × 0.12 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4705 independent reflections
Radiation source: fine-focus sealed tube	3503 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ω scan	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −21→21
T_min = 0.810, T_max = 0.867	k = −19→19
61947 measured reflections	l = −21→21

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0521P)² + 1.0723P] where P = (F_o² + 2F_c²)/3
4705 reflections	(Δ/σ)_max = 0.001
334 parameters	Δρ_max = 0.84 e Å⁻³
11 restraints	Δρ_min = −0.87 e Å⁻³

Crystal data top

[Cd(C₁₀H₈N₂)(H₂O)₄](C₇H₄O₆S)·H₂O	V = 4124.9 (5) Å³
M_r = 574.83	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 16.3246 (10) Å	µ = 1.23 mm⁻¹
b = 15.3063 (11) Å	T = 293 K
c = 16.5084 (10) Å	0.18 × 0.16 × 0.12 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4705 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3503 reflections with I > 2σ(I)
T_min = 0.810, T_max = 0.867	R_int = 0.057
61947 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	11 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.84 e Å⁻³
4705 reflections	Δρ_min = −0.87 e Å⁻³
334 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cd1	0.5000	0.440537 (18)	0.7500	0.02271 (9)
Cd2	1.0000	0.521170 (18)	1.2500	0.02318 (9)
S1	0.27334 (4)	0.28183 (4)	0.28084 (4)	0.02442 (16)
O1	0.47567 (13)	0.21091 (14)	0.60407 (12)	0.0361 (5)
O2	0.52506 (13)	0.20519 (13)	0.47897 (12)	0.0312 (5)
O3	0.15128 (12)	0.29724 (14)	0.41107 (13)	0.0340 (5)
H3	0.1118 (15)	0.299 (2)	0.4435 (18)	0.058 (12)*
O4	0.23985 (15)	0.36795 (13)	0.26880 (13)	0.0434 (6)
O5	0.21871 (16)	0.21217 (13)	0.25558 (11)	0.0375 (6)
O6	0.35463 (14)	0.27325 (16)	0.24423 (11)	0.0402 (6)
O1W	0.57110 (17)	0.34037 (17)	0.67867 (17)	0.0513 (6)
H11	0.613 (2)	0.322 (3)	0.702 (3)	0.108 (19)*
H12	0.544 (3)	0.296 (2)	0.665 (3)	0.088 (17)*
O2W	0.43176 (16)	0.55653 (16)	0.81748 (14)	0.0393 (5)
H21	0.398 (2)	0.590 (2)	0.794 (3)	0.087 (16)*
H22	0.469 (2)	0.589 (3)	0.835 (3)	0.081 (16)*
O3W	1.06793 (15)	0.62827 (16)	1.17301 (14)	0.0417 (5)
H31	1.0408 (19)	0.650 (2)	1.1351 (15)	0.047 (11)*
H32	1.090 (2)	0.668 (2)	1.201 (2)	0.075 (14)*
O4W	0.91413 (15)	0.41573 (15)	1.30228 (15)	0.0397 (5)
H41	0.934 (2)	0.376 (2)	1.331 (2)	0.075 (14)*
H42	0.880 (2)	0.396 (3)	1.270 (2)	0.067 (14)*
O5W	0.55474 (18)	0.35179 (16)	0.38410 (18)	0.0548 (7)
H51	0.549 (3)	0.313 (2)	0.420 (2)	0.088 (16)*
H52	0.592 (2)	0.338 (4)	0.351 (3)	0.12 (2)*
N1	0.59742 (14)	0.45225 (15)	0.85125 (13)	0.0250 (5)
N2	0.90277 (14)	0.52540 (14)	1.14842 (13)	0.0233 (5)
C1	0.58037 (17)	0.44761 (19)	0.93036 (17)	0.0295 (6)
H1	0.5280	0.4308	0.9461	0.035*
C2	0.63744 (18)	0.46683 (19)	0.98969 (17)	0.0283 (6)
H2	0.6228	0.4640	1.0441	0.034*
C3	0.71664 (17)	0.49032 (17)	0.96802 (16)	0.0237 (6)
C4	0.73372 (18)	0.4948 (2)	0.88558 (17)	0.0318 (6)
H4	0.7857	0.5106	0.8679	0.038*
C5	0.67325 (18)	0.47571 (19)	0.83037 (17)	0.0313 (7)
H5	0.6859	0.4794	0.7755	0.038*
C6	0.82516 (17)	0.54887 (18)	1.16227 (16)	0.0259 (6)
H6	0.8120	0.5719	1.2127	0.031*
C7	0.76329 (17)	0.54064 (17)	1.10549 (17)	0.0270 (6)
H7	0.7102	0.5577	1.1182	0.032*
C8	0.78081 (16)	0.50689 (17)	1.02957 (16)	0.0228 (5)
C9	0.86225 (18)	0.48489 (19)	1.01436 (17)	0.0297 (6)
H9	0.8775	0.4641	0.9636	0.036*
C10	0.92024 (17)	0.4940 (2)	1.07458 (17)	0.0307 (6)
H10	0.9739	0.4777	1.0634	0.037*
C11	0.46607 (17)	0.21484 (17)	0.52932 (17)	0.0257 (6)
C12	0.38208 (16)	0.23377 (16)	0.49698 (15)	0.0230 (5)
C13	0.31673 (17)	0.24312 (19)	0.55095 (16)	0.0291 (6)
H13	0.3255	0.2352	0.6061	0.035*
C14	0.23932 (17)	0.26394 (19)	0.52330 (18)	0.0314 (6)
H14	0.1963	0.2694	0.5599	0.038*
C15	0.22524 (16)	0.27683 (17)	0.44052 (16)	0.0247 (6)
C16	0.29036 (16)	0.26767 (17)	0.38635 (15)	0.0219 (5)
C17	0.36795 (15)	0.24627 (17)	0.41485 (15)	0.0226 (5)
H17	0.4110	0.2402	0.3784	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.01869 (15)	0.02822 (17)	0.02123 (15)	0.000	−0.00454 (10)	0.000
Cd2	0.01997 (16)	0.02926 (17)	0.02031 (15)	0.000	−0.00523 (10)	0.000
S1	0.0210 (3)	0.0301 (3)	0.0222 (3)	0.0000 (3)	−0.0007 (3)	−0.0001 (3)
O1	0.0266 (10)	0.0589 (15)	0.0229 (10)	−0.0022 (9)	−0.0043 (9)	0.0086 (9)
O2	0.0193 (9)	0.0450 (12)	0.0293 (10)	0.0032 (9)	0.0011 (8)	0.0042 (9)
O3	0.0146 (10)	0.0531 (14)	0.0344 (11)	0.0061 (9)	0.0003 (9)	−0.0076 (10)
O4	0.0603 (16)	0.0316 (11)	0.0384 (12)	0.0103 (11)	−0.0041 (11)	0.0065 (9)
O5	0.0385 (13)	0.0429 (13)	0.0311 (12)	−0.0131 (10)	−0.0075 (9)	−0.0063 (9)
O6	0.0259 (12)	0.0698 (16)	0.0250 (11)	0.0036 (11)	0.0068 (8)	0.0025 (10)
O1W	0.0437 (16)	0.0475 (15)	0.0626 (17)	0.0170 (13)	−0.0110 (13)	−0.0224 (13)
O2W	0.0416 (15)	0.0423 (13)	0.0341 (12)	0.0117 (12)	0.0008 (11)	−0.0035 (10)
O3W	0.0479 (15)	0.0411 (13)	0.0360 (12)	−0.0127 (11)	−0.0121 (11)	0.0125 (11)
O4W	0.0333 (13)	0.0401 (13)	0.0457 (14)	−0.0076 (10)	−0.0082 (11)	0.0139 (11)
O5W	0.0587 (18)	0.0380 (14)	0.0675 (18)	0.0051 (12)	0.0140 (15)	0.0150 (13)
N1	0.0229 (12)	0.0302 (12)	0.0220 (11)	0.0000 (10)	−0.0062 (10)	−0.0019 (10)
N2	0.0215 (12)	0.0281 (12)	0.0202 (11)	−0.0024 (9)	−0.0063 (9)	0.0011 (9)
C1	0.0218 (14)	0.0377 (16)	0.0290 (15)	−0.0049 (12)	−0.0015 (12)	0.0035 (12)
C2	0.0270 (15)	0.0381 (15)	0.0198 (13)	−0.0031 (12)	−0.0010 (11)	0.0020 (12)
C3	0.0226 (14)	0.0263 (13)	0.0222 (12)	0.0002 (11)	−0.0046 (12)	0.0001 (10)
C4	0.0192 (14)	0.0518 (17)	0.0245 (14)	−0.0046 (13)	−0.0006 (11)	0.0010 (13)
C5	0.0239 (15)	0.0512 (19)	0.0189 (13)	−0.0016 (13)	−0.0019 (11)	−0.0010 (12)
C6	0.0257 (15)	0.0301 (14)	0.0219 (13)	−0.0033 (12)	0.0003 (11)	−0.0031 (11)
C7	0.0202 (14)	0.0355 (15)	0.0252 (14)	−0.0009 (12)	−0.0019 (11)	−0.0003 (12)
C8	0.0214 (13)	0.0257 (13)	0.0213 (12)	−0.0005 (11)	−0.0041 (12)	0.0026 (10)
C9	0.0239 (15)	0.0411 (17)	0.0240 (13)	0.0035 (12)	−0.0031 (12)	−0.0047 (12)
C10	0.0217 (14)	0.0425 (16)	0.0278 (15)	0.0033 (13)	−0.0029 (12)	−0.0040 (13)
C11	0.0206 (14)	0.0292 (14)	0.0273 (14)	−0.0024 (11)	0.0014 (12)	0.0059 (11)
C12	0.0179 (13)	0.0266 (13)	0.0246 (13)	−0.0010 (11)	−0.0008 (10)	0.0017 (11)
C13	0.0260 (15)	0.0388 (16)	0.0225 (13)	−0.0004 (13)	0.0001 (11)	0.0026 (12)
C14	0.0248 (15)	0.0430 (17)	0.0263 (14)	0.0013 (13)	0.0089 (12)	−0.0015 (12)
C15	0.0155 (12)	0.0287 (14)	0.0298 (14)	0.0007 (11)	−0.0031 (11)	−0.0027 (11)
C16	0.0213 (13)	0.0229 (13)	0.0217 (12)	−0.0014 (10)	0.0001 (11)	−0.0020 (10)
C17	0.0172 (13)	0.0238 (13)	0.0268 (13)	−0.0016 (10)	0.0028 (11)	−0.0035 (11)

Geometric parameters (Å, º) top

Cd1—O1Wⁱ	2.255 (2)	N1—C1	1.337 (3)
Cd1—O1W	2.255 (2)	N2—C6	1.337 (3)
Cd1—N1	2.314 (2)	N2—C10	1.341 (3)
Cd1—N1ⁱ	2.314 (2)	C1—C2	1.383 (4)
Cd1—O2W	2.374 (2)	C1—H1	0.9300
Cd1—O2Wⁱ	2.374 (2)	C2—C3	1.389 (4)
Cd2—O4W	2.305 (2)	C2—H2	0.9300
Cd2—O4Wⁱⁱ	2.305 (2)	C3—C4	1.391 (4)
Cd2—N2ⁱⁱ	2.310 (2)	C3—C8	1.481 (4)
Cd2—N2	2.310 (2)	C4—C5	1.375 (4)
Cd2—O3Wⁱⁱ	2.352 (2)	C4—H4	0.9300
Cd2—O3W	2.352 (2)	C5—H5	0.9300
S1—O4	1.441 (2)	C6—C7	1.384 (4)
S1—O5	1.451 (2)	C6—H6	0.9300
S1—O6	1.464 (2)	C7—C8	1.385 (4)
S1—C16	1.777 (3)	C7—H7	0.9300
O1—C11	1.245 (3)	C8—C9	1.394 (4)
O2—C11	1.281 (4)	C9—C10	1.380 (4)
O3—C15	1.338 (3)	C9—H9	0.9300
O3—H3	0.838 (10)	C10—H10	0.9300
O1W—H11	0.838 (10)	C11—C12	1.500 (4)
O1W—H12	0.842 (10)	C12—C17	1.388 (3)
O2W—H21	0.842 (10)	C12—C13	1.397 (4)
O2W—H22	0.840 (10)	C13—C14	1.381 (4)
O3W—H31	0.835 (10)	C13—H13	0.9300
O3W—H32	0.840 (10)	C14—C15	1.400 (4)
O4W—H41	0.838 (10)	C14—H14	0.9300
O4W—H42	0.835 (10)	C15—C16	1.396 (4)
O5W—H51	0.842 (10)	C16—C17	1.390 (3)
O5W—H52	0.840 (10)	C17—H17	0.9300
N1—C5	1.334 (4)

O1Wⁱ—Cd1—O1W	94.32 (16)	C6—N2—Cd2	122.33 (17)
O1Wⁱ—Cd1—N1	91.68 (9)	C10—N2—Cd2	120.25 (18)
O1W—Cd1—N1	94.36 (9)	N1—C1—C2	122.7 (3)
O1Wⁱ—Cd1—N1ⁱ	94.36 (9)	N1—C1—H1	118.7
O1W—Cd1—N1ⁱ	91.68 (9)	C2—C1—H1	118.7
N1—Cd1—N1ⁱ	171.11 (11)	C1—C2—C3	120.0 (3)
O1Wⁱ—Cd1—O2W	91.26 (10)	C1—C2—H2	120.0
O1W—Cd1—O2W	174.42 (10)	C3—C2—H2	120.0
N1—Cd1—O2W	85.73 (8)	C2—C3—C4	116.8 (3)
N1ⁱ—Cd1—O2W	87.62 (8)	C2—C3—C8	121.7 (2)
O1Wⁱ—Cd1—O2Wⁱ	174.42 (10)	C4—C3—C8	121.4 (3)
O1W—Cd1—O2Wⁱ	91.26 (10)	C5—C4—C3	119.6 (3)
N1—Cd1—O2Wⁱ	87.62 (8)	C5—C4—H4	120.2
N1ⁱ—Cd1—O2Wⁱ	85.73 (8)	C3—C4—H4	120.2
O2W—Cd1—O2Wⁱ	83.17 (12)	N1—C5—C4	123.5 (3)
O4W—Cd2—O4Wⁱⁱ	91.14 (13)	N1—C5—H5	118.2
O4W—Cd2—N2ⁱⁱ	99.54 (8)	C4—C5—H5	118.2
O4Wⁱⁱ—Cd2—N2ⁱⁱ	82.74 (8)	N2—C6—C7	123.5 (2)
O4W—Cd2—N2	82.74 (8)	N2—C6—H6	118.3
O4Wⁱⁱ—Cd2—N2	99.54 (8)	C7—C6—H6	118.3
N2ⁱⁱ—Cd2—N2	176.79 (11)	C6—C7—C8	119.7 (3)
O4W—Cd2—O3Wⁱⁱ	89.94 (9)	C6—C7—H7	120.1
O4Wⁱⁱ—Cd2—O3Wⁱⁱ	167.66 (8)	C8—C7—H7	120.1
N2ⁱⁱ—Cd2—O3Wⁱⁱ	84.96 (8)	C7—C8—C9	116.7 (2)
N2—Cd2—O3Wⁱⁱ	92.80 (8)	C7—C8—C3	122.6 (3)
O4W—Cd2—O3W	167.66 (8)	C9—C8—C3	120.6 (3)
O4Wⁱⁱ—Cd2—O3W	89.94 (9)	C10—C9—C8	120.0 (3)
N2ⁱⁱ—Cd2—O3W	92.80 (8)	C10—C9—H9	120.0
N2—Cd2—O3W	84.96 (8)	C8—C9—H9	120.0
O3Wⁱⁱ—Cd2—O3W	91.63 (13)	N2—C10—C9	123.1 (3)
O4—S1—O5	113.53 (15)	N2—C10—H10	118.5
O4—S1—O6	111.66 (14)	C9—C10—H10	118.5
O5—S1—O6	111.87 (14)	O1—C11—O2	122.9 (3)
O4—S1—C16	107.83 (13)	O1—C11—C12	118.5 (2)
O5—S1—C16	106.75 (12)	O2—C11—C12	118.6 (3)
O6—S1—C16	104.60 (12)	C17—C12—C13	118.8 (2)
C15—O3—H3	118 (3)	C17—C12—C11	121.7 (2)
Cd1—O1W—H11	114 (4)	C13—C12—C11	119.4 (2)
Cd1—O1W—H12	115 (4)	C14—C13—C12	120.8 (2)
H11—O1W—H12	106 (5)	C14—C13—H13	119.6
Cd1—O2W—H21	123 (3)	C12—C13—H13	119.6
Cd1—O2W—H22	105 (3)	C13—C14—C15	120.4 (3)
H21—O2W—H22	106 (4)	C13—C14—H14	119.8
Cd2—O3W—H31	116 (3)	C15—C14—H14	119.8
Cd2—O3W—H32	114 (3)	O3—C15—C16	118.5 (2)
H31—O3W—H32	111 (4)	O3—C15—C14	122.4 (3)
Cd2—O4W—H41	119 (3)	C16—C15—C14	119.1 (2)
Cd2—O4W—H42	115 (3)	C17—C16—C15	120.0 (2)
H41—O4W—H42	111 (4)	C17—C16—S1	120.2 (2)
H51—O5W—H52	111 (5)	C15—C16—S1	119.8 (2)
C5—N1—C1	117.4 (2)	C12—C17—C16	120.9 (2)
C5—N1—Cd1	118.16 (18)	C12—C17—H17	119.5
C1—N1—Cd1	123.94 (19)	C16—C17—H17	119.5
C6—N2—C10	117.0 (2)

O1Wⁱ—Cd1—N1—C5	152.5 (2)	C4—C3—C8—C7	150.8 (3)
O1W—Cd1—N1—C5	58.0 (2)	C2—C3—C8—C9	145.6 (3)
O2W—Cd1—N1—C5	−116.4 (2)	C4—C3—C8—C9	−32.3 (4)
O2Wⁱ—Cd1—N1—C5	−33.0 (2)	C7—C8—C9—C10	2.4 (4)
O1Wⁱ—Cd1—N1—C1	−36.2 (2)	C3—C8—C9—C10	−174.7 (3)
O1W—Cd1—N1—C1	−130.6 (2)	C6—N2—C10—C9	−0.4 (4)
O2W—Cd1—N1—C1	55.0 (2)	Cd2—N2—C10—C9	171.9 (2)
O2Wⁱ—Cd1—N1—C1	138.3 (2)	C8—C9—C10—N2	−1.5 (5)
O4W—Cd2—N2—C6	62.7 (2)	O1—C11—C12—C17	174.6 (2)
O4Wⁱⁱ—Cd2—N2—C6	152.6 (2)	O2—C11—C12—C17	−4.0 (4)
O3Wⁱⁱ—Cd2—N2—C6	−26.9 (2)	O1—C11—C12—C13	−2.4 (4)
O3W—Cd2—N2—C6	−118.3 (2)	O2—C11—C12—C13	179.0 (2)
O4W—Cd2—N2—C10	−109.3 (2)	C17—C12—C13—C14	0.4 (4)
O4Wⁱⁱ—Cd2—N2—C10	−19.3 (2)	C11—C12—C13—C14	177.5 (3)
O3Wⁱⁱ—Cd2—N2—C10	161.2 (2)	C12—C13—C14—C15	−0.6 (4)
O3W—Cd2—N2—C10	69.8 (2)	C13—C14—C15—O3	−179.9 (3)
C5—N1—C1—C2	0.7 (4)	C13—C14—C15—C16	0.5 (4)
Cd1—N1—C1—C2	−170.7 (2)	O3—C15—C16—C17	−179.8 (2)
N1—C1—C2—C3	−1.4 (5)	C14—C15—C16—C17	−0.2 (4)
C1—C2—C3—C4	1.2 (4)	O3—C15—C16—S1	−0.8 (3)
C1—C2—C3—C8	−176.7 (3)	C14—C15—C16—S1	178.9 (2)
C2—C3—C4—C5	−0.4 (4)	O4—S1—C16—C17	−123.5 (2)
C8—C3—C4—C5	177.5 (3)	O5—S1—C16—C17	114.2 (2)
C1—N1—C5—C4	0.2 (4)	O6—S1—C16—C17	−4.5 (3)
Cd1—N1—C5—C4	172.1 (2)	O4—S1—C16—C15	57.5 (2)
C3—C4—C5—N1	−0.3 (5)	O5—S1—C16—C15	−64.9 (2)
C10—N2—C6—C7	1.3 (4)	O6—S1—C16—C15	176.4 (2)
Cd2—N2—C6—C7	−170.8 (2)	C13—C12—C17—C16	0.0 (4)
N2—C6—C7—C8	−0.3 (4)	C11—C12—C17—C16	−177.1 (2)
C6—C7—C8—C9	−1.6 (4)	C15—C16—C17—C12	−0.1 (4)
C6—C7—C8—C3	175.5 (2)	S1—C16—C17—C12	−179.1 (2)
C2—C3—C8—C7	−31.4 (4)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+2, y, −z+5/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O5ⁱⁱⁱ	0.84 (1)	1.93 (1)	2.762 (4)	171 (5)
O1w—H12···O1	0.84 (1)	1.99 (2)	2.805 (3)	163 (5)
O2w—H21···O6^iv	0.84 (1)	2.36 (2)	3.136 (3)	154 (4)
O2w—H22···O5w^iv	0.84 (1)	1.85 (1)	2.685 (4)	173 (5)
O3w—H31···O2^v	0.84 (1)	2.08 (2)	2.858 (3)	155 (3)
O3w—H32···O6^vi	0.84 (1)	1.99 (1)	2.812 (3)	167 (4)
O4w—H41···O1^vii	0.84 (1)	1.84 (1)	2.675 (3)	178 (4)
O4w—H42···O4ⁱ	0.84 (1)	2.10 (2)	2.869 (3)	154 (4)
O5w—H51···O2	0.84 (1)	1.96 (2)	2.779 (3)	166 (5)
O5w—H52···O6^viii	0.84 (1)	2.06 (2)	2.850 (4)	157 (6)
O3—H3···O2^ix	0.84 (1)	1.91 (1)	2.746 (3)	176 (4)

Symmetry codes: (i) −x+1, y, −z+3/2; (iii) x+1/2, −y+1/2, −z+1; (iv) x, −y+1, z+1/2; (v) x+1/2, y+1/2, −z+3/2; (vi) −x+3/2, y+1/2, z+1; (vii) x+1/2, −y+1/2, −z+2; (viii) −x+1, y, −z+1/2; (ix) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cd(C₁₀H₈N₂)(H₂O)₄](C₇H₄O₆S)·H₂O
M_r	574.83
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	16.3246 (10), 15.3063 (11), 16.5084 (10)
V (Å³)	4124.9 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.18 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.810, 0.867
No. of measured, independent and observed [I > 2σ(I)] reflections	61947, 4705, 3503
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.090, 1.04
No. of reflections	4705
No. of parameters	334
No. of restraints	11
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.87

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O5ⁱ	0.84 (1)	1.93 (1)	2.762 (4)	171 (5)
O1w—H12···O1	0.84 (1)	1.99 (2)	2.805 (3)	163 (5)
O2w—H21···O6ⁱⁱ	0.84 (1)	2.36 (2)	3.136 (3)	154 (4)
O2w—H22···O5wⁱⁱ	0.84 (1)	1.85 (1)	2.685 (4)	173 (5)
O3w—H31···O2ⁱⁱⁱ	0.84 (1)	2.08 (2)	2.858 (3)	155 (3)
O3w—H32···O6^iv	0.84 (1)	1.99 (1)	2.812 (3)	167 (4)
O4w—H41···O1^v	0.84 (1)	1.84 (1)	2.675 (3)	178 (4)
O4w—H42···O4^vi	0.84 (1)	2.10 (2)	2.869 (3)	154 (4)
O5w—H51···O2	0.84 (1)	1.96 (2)	2.779 (3)	166 (5)
O5w—H52···O6^vii	0.84 (1)	2.06 (2)	2.850 (4)	157 (6)
O3—H3···O2^viii	0.84 (1)	1.91 (1)	2.746 (3)	176 (4)

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x, −y+1, z+1/2; (iii) x+1/2, y+1/2, −z+3/2; (iv) −x+3/2, y+1/2, z+1; (v) x+1/2, −y+1/2, −z+2; (vi) −x+1, y, −z+3/2; (vii) −x+1, y, −z+1/2; (viii) x−1/2, −y+1/2, −z+1.

Acknowledgements

This work was supported by the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (Nos. 12511z023 and 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 t d03), Heilongjiang University (Hdtd2010–04) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12).

References

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