catena-Poly[[[(2-phenyl­acetato-κO)zinc(II)]bis­[μ-4,4′-(disulfanedi­yl)dipyridine-κ2N:N′]] monohydrate]

Zhang, J.; Xu, W.

doi:10.1107/S1600536810021331

catena-Poly[[[(2-phenylacetato-κO)zinc(II)]bis[μ-4,4′-(disulfanediyl)dipyridine-κ²N:N′]] monohydrate]

In the title compound, {[Zn(C₈H₇O₂)₂(C₁₀H₈N₂S₂)₂]·H₂O}_n, the Zn^II atom is coordinated by four N atoms from four 4,4′-(disulfanediyl)dipyridine (bpds) ligands and two O atoms from two 2-phenylacetate anions in a distorted octahedral coordination geometry. The two bpds ligands of the same axial chirality bridge Zn^II atoms, generating repeated rhomboidal chains, which are linked by O—H

O hydrogen bonds into a ladder structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810021331/er2078sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810021331/er2078Isup2.hkl Contains datablock I

CCDC reference: 786439

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R factor = 0.035
wR factor = 0.092
Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) .....         13

Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =       8.02
            Cell volume su given      =       6.00
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn     --  O1      ..       7.45 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C22
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C30
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C29
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600        152
PLAT152_ALERT_1_C The Supplied and Calc. Volume s.u. Differ by ...          2 Units
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        144

Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT804_ALERT_5_G ARU-Pack Problem in PLATON Analysis ............          1 Times

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Recently, a variety of pyridyl-donor ligands have been widely employ to construct coordination polymers with intriguing topologies and unexpected properties (Biradha et al., 2006; Liu et al., 2008; Hernández-Ahuactzi et al., 2008; Ma, Wang, Hu et al., 2009). 4,4'-dipyridyl disulfide (bpds) is a bipyridyl-type ligand with a twisted structuret. Addtionally, bpds ligand has axial chirality. A number of coordination polymers containing bpds ligand have been reported (Horikoshi et al., 2006; Carballo et al., 2008; Ma, Wang, Wang et al., 2009). Phenylacetic acid is one of the most common carboxylate ligands and can adopt different coordination modes (Johnston et al., 2008). However, the coordination polymers based on mixed bpds and phenylacetate anion have not been reported to date. In this paper, we report the title Znic polymeric compound, [{Zn(bpds)₂(C₆H₅CH₂COO)₂}.H₂O]_n with a 1D repeated rhomboidal chain structure. The unsymmetrical unit of the title compound consisits of one Zn²⁺ cation, two bpds molecules of the same chirality, two phenylacetate anions and one lattice water molecule (Fig.1).The M- and P- bpds molecules act as bis-monodentate bridging ligands with the C—S—S—C torsion angle being 97.10 (1)° and 93.40 (1)°, respectively, and the corresponding py ring planes form dihedral angles of 89.06 (6)° and 79.42 (6)°. Both crystallographically distinct phenylacetate anions monodentately coordinate to the metal atoms.The Zn atom has a distorted octahedral environment, being surrounded by two nitrogen atoms from two M-bpds and two nitrogen atoms from two P-bpds in the equatorial plane, and by two oxygen atoms from two crystallographically distinct phenylacetate anions occupying the axial positions. The corresponding bond distances range from 2.111 (2)Å to 2.202 (2) Å, and the bond angles in the region 84.12 (7)—175.94 (7)° deviate from the values of 90° and 180° for an ideal octahedron (table 1). Along the [110] direction, the two bpds ligands of the same chirality bridge Zn atoms to form 1D repeated rhomboidal chains(Fig. 2), which is similar with the structures of the reported zinc coordination polymers based on bpds ligand (Horikoshi et al., 2005). The Zn···Zn separation through bpds ligands is 11.187 Å. The lattice water form hydrogen bonds to the uncoordinated carboxylate oxygen atoms of two different phenylacetate anions. In this way, the adjacent chains are linked by water molecules to give a ladder structure.

Related literature top

For coordination chemistry based on pyridyl donor ligands, see: Biradha et al. (2006); Liu et al. (2008); Hernández-Ahuactzi et al. (2008); Ma, Wang, Hu OK? et al. (2009). For bpds compounds, see: Horikoshi et al. (2006); Carballo et al. (2008); Ma, Wang, Wang OK? et al. (2009; Horikoshi et al. (2005). For compounds containing phenylacetic acid, see: Johnston et al. (2008).

Experimental top

0.0750 g (0.25 mmol) Zn(NO₃)₂.6H₂O and 0.0345 g (0.25 mmol) phenylacetic acid were succesively dissolved in a stirred aqueous ethanolic solution consisting of 5 ml EtOH and 10 ml H₂O, to which 0.5 ml 1.0 M NaOH was added. The formed white suspension was stirred at 80°C for 30 min and then added was an ethanolic solution of 0.0570 g (0.25 mmol) 4,4'-dipyridyldisulfide in 5 ml EtOH. The final mixture was further stirred at 75°C for 1 h and filtered off. The colorless filtrate (pH=6.02) was left standing at room temperature for one week affording colorless block-like crystals (yield: 4 mg).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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. View of the molecular of the title compound, Displacement ellipsoids are drawn at the 45% probability level.
	Fig. 2. 1D repeated rhomboidal chains in the title compound.
	Fig. 3. The ladder structure of the title compound.

catena-Poly[[[(2-phenylacetato-κO)zinc(II)]bis[µ-4,4'- (disulfanediyl)dipyridine-κ²N:N']] monohydrate] top

Crystal data top

[Zn(C₈H₇O₂)₂(C₁₀H₈N₂S₂)₂]·H₂O	Z = 2
M_r = 794.27	F(000) = 820
Triclinic, P1	D_x = 1.483 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.851 (2) Å	Cell parameters from 16701 reflections
b = 11.130 (2) Å	θ = 3.1–27.5°
c = 18.319 (4) Å	µ = 0.97 mm⁻¹
α = 90.38 (3)°	T = 295 K
β = 98.88 (3)°	Block, colorless
γ = 115.89 (3)°	0.51 × 0.41 × 0.36 mm
V = 1779.0 (6) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	7859 independent reflections
Radiation source: fine-focus sealed tube	6036 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→14
T_min = 0.623, T_max = 0.701	l = −23→23
16701 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0395P)² + 0.3693P] where P = (F_o² + 2F_c²)/3
7859 reflections	(Δ/σ)_max = 0.001
451 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Zn(C₈H₇O₂)₂(C₁₀H₈N₂S₂)₂]·H₂O	γ = 115.89 (3)°
M_r = 794.27	V = 1779.0 (6) Å³
Triclinic, P1	Z = 2
a = 9.851 (2) Å	Mo Kα radiation
b = 11.130 (2) Å	µ = 0.97 mm⁻¹
c = 18.319 (4) Å	T = 295 K
α = 90.38 (3)°	0.51 × 0.41 × 0.36 mm
β = 98.88 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	7859 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	6036 reflections with I > 2σ(I)
T_min = 0.623, T_max = 0.701	R_int = 0.038
16701 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.07	Δρ_max = 0.43 e Å⁻³
7859 reflections	Δρ_min = −0.34 e Å⁻³
451 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Zn	0.42078 (3)	0.23364 (2)	0.254511 (13)	0.03328 (8)
N1	0.21801 (19)	0.10323 (18)	0.17515 (9)	0.0351 (4)
C1	0.1234 (2)	0.1508 (2)	0.14209 (11)	0.0353 (5)
H1A	0.1526	0.2422	0.1492	0.042*
C2	−0.0162 (2)	0.0710 (2)	0.09761 (12)	0.0355 (5)
H2A	−0.0790	0.1081	0.0755	0.043*
C3	−0.0604 (2)	−0.0650 (2)	0.08669 (11)	0.0336 (5)
C4	0.0375 (3)	−0.1155 (2)	0.12028 (14)	0.0457 (6)
H4A	0.0115	−0.2064	0.1141	0.055*
C5	0.1747 (3)	−0.0276 (2)	0.16317 (14)	0.0463 (6)
H5A	0.2407	−0.0617	0.1850	0.056*
S1	−0.24164 (6)	−0.16230 (6)	0.03032 (3)	0.03988 (14)
S2	−0.24204 (6)	−0.34128 (6)	0.00746 (3)	0.04027 (14)
C6	−0.3406 (2)	−0.4474 (2)	0.07251 (11)	0.0344 (5)
C7	−0.3961 (3)	−0.4103 (2)	0.12877 (13)	0.0476 (6)
H7A	−0.3824	−0.3226	0.1357	0.057*
C8	−0.4725 (3)	−0.5053 (2)	0.17481 (13)	0.0466 (6)
H8A	−0.5116	−0.4795	0.2118	0.056*
N2	−0.4932 (2)	−0.63104 (18)	0.16917 (9)	0.0339 (4)
C9	−0.4425 (2)	−0.6675 (2)	0.11302 (12)	0.0377 (5)
H9A	−0.4595	−0.7563	0.1069	0.045*
C10	−0.3665 (2)	−0.5801 (2)	0.06409 (12)	0.0377 (5)
H10A	−0.3330	−0.6094	0.0260	0.045*
N3	0.61670 (19)	0.37405 (18)	0.33457 (10)	0.0355 (4)
C11	0.5949 (2)	0.4081 (2)	0.40060 (12)	0.0358 (5)
H11A	0.4977	0.3640	0.4128	0.043*
C12	0.7090 (2)	0.5050 (2)	0.45119 (12)	0.0359 (5)
H12A	0.6889	0.5262	0.4962	0.043*
C13	0.8547 (2)	0.5704 (2)	0.43370 (11)	0.0335 (5)
C14	0.8780 (2)	0.5378 (2)	0.36502 (12)	0.0398 (5)
H14A	0.9735	0.5818	0.3509	0.048*
C15	0.7571 (2)	0.4390 (2)	0.31818 (12)	0.0415 (5)
H15A	0.7740	0.4163	0.2726	0.050*
S3	0.99682 (6)	0.69153 (6)	0.50235 (3)	0.04202 (15)
S4	1.20007 (6)	0.72797 (6)	0.47202 (3)	0.04384 (15)
C16	1.2462 (2)	0.8675 (2)	0.41869 (11)	0.0339 (5)
C17	1.1450 (2)	0.9135 (2)	0.38416 (12)	0.0379 (5)
H17A	1.0420	0.8714	0.3883	0.046*
C18	1.2001 (2)	1.0225 (2)	0.34368 (13)	0.0402 (5)
H18A	1.1317	1.0540	0.3214	0.048*
N4	1.34608 (19)	1.08651 (18)	0.33422 (10)	0.0357 (4)
C19	1.4430 (2)	1.0421 (2)	0.36901 (12)	0.0393 (5)
H19A	1.5457	1.0869	0.3644	0.047*
C20	1.3994 (2)	0.9344 (2)	0.41103 (12)	0.0381 (5)
H20A	1.4707	0.9066	0.4339	0.046*
O1	0.29666 (17)	0.33877 (16)	0.27800 (8)	0.0414 (4)
O2	0.2410 (2)	0.3097 (2)	0.39220 (9)	0.0544 (5)
C21	0.2319 (3)	0.3518 (2)	0.33031 (13)	0.0389 (5)
C22	0.1335 (4)	0.4250 (4)	0.31603 (16)	0.0678 (9)
H22A	0.0295	0.3630	0.3204	0.081*
H22B	0.1692	0.4966	0.3551	0.081*
C23	0.1282 (3)	0.4843 (3)	0.24333 (15)	0.0494 (6)
C24	0.2307 (3)	0.6123 (3)	0.23429 (19)	0.0666 (8)
H24A	0.3012	0.6656	0.2750	0.080*
C25	0.2315 (5)	0.6642 (4)	0.1657 (2)	0.0866 (11)
H25A	0.3032	0.7509	0.1605	0.104*
C26	0.1280 (6)	0.5887 (6)	0.1063 (2)	0.0942 (13)
H26A	0.1294	0.6230	0.0601	0.113*
C27	0.0224 (5)	0.4634 (5)	0.1139 (2)	0.0892 (12)
H27A	−0.0500	0.4121	0.0732	0.107*
C28	0.0224 (4)	0.4120 (3)	0.18197 (19)	0.0687 (8)
H28A	−0.0513	0.3259	0.1866	0.082*
O3	0.57013 (19)	0.14005 (17)	0.23618 (8)	0.0453 (4)
O4	0.5095 (3)	0.0218 (2)	0.12864 (11)	0.0731 (6)
C29	0.5861 (3)	0.0632 (2)	0.19184 (13)	0.0426 (5)
C30	0.7158 (4)	0.0237 (3)	0.21550 (17)	0.0652 (8)
H30A	0.7119	−0.0377	0.1765	0.078*
H30B	0.8123	0.1035	0.2188	0.078*
C31	0.7172 (3)	−0.0404 (3)	0.28744 (15)	0.0469 (6)
C32	0.6281 (3)	−0.1760 (3)	0.28977 (17)	0.0618 (7)
H32A	0.5654	−0.2267	0.2466	0.074*
C33	0.6295 (4)	−0.2379 (3)	0.35429 (19)	0.0706 (8)
H33A	0.5680	−0.3294	0.3543	0.085*
C34	0.7211 (4)	−0.1654 (3)	0.41871 (18)	0.0663 (8)
H34A	0.7226	−0.2070	0.4625	0.080*
C35	0.8096 (4)	−0.0319 (3)	0.41752 (18)	0.0669 (8)
H35A	0.8717	0.0182	0.4610	0.080*
C36	0.8088 (3)	0.0305 (3)	0.35277 (17)	0.0605 (7)
H36A	0.8710	0.1219	0.3532	0.073*
O5	0.3132 (3)	−0.1386 (2)	−0.00858 (12)	0.0856 (7)
H5C	0.3720	−0.0885	−0.0334	0.128*
H5D	0.3676	−0.1044	0.0305	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.03625 (14)	0.03132 (15)	0.02738 (13)	0.01058 (10)	0.00539 (10)	0.00328 (10)
N1	0.0369 (9)	0.0334 (10)	0.0314 (9)	0.0130 (8)	0.0037 (7)	0.0012 (8)
C1	0.0399 (11)	0.0305 (12)	0.0318 (11)	0.0115 (9)	0.0082 (9)	0.0051 (9)
C2	0.0368 (11)	0.0356 (13)	0.0333 (11)	0.0150 (9)	0.0071 (9)	0.0074 (9)
C3	0.0330 (10)	0.0357 (12)	0.0280 (10)	0.0101 (9)	0.0095 (8)	0.0065 (9)
C4	0.0469 (13)	0.0306 (13)	0.0532 (15)	0.0148 (10)	−0.0018 (11)	−0.0016 (11)
C5	0.0451 (13)	0.0415 (15)	0.0502 (15)	0.0213 (11)	−0.0035 (11)	−0.0019 (11)
S1	0.0346 (3)	0.0371 (3)	0.0383 (3)	0.0079 (2)	0.0035 (2)	0.0064 (2)
S2	0.0414 (3)	0.0367 (3)	0.0326 (3)	0.0064 (2)	0.0119 (2)	0.0028 (2)
C6	0.0305 (10)	0.0361 (12)	0.0299 (11)	0.0087 (8)	0.0052 (8)	0.0044 (9)
C7	0.0703 (16)	0.0278 (12)	0.0451 (14)	0.0171 (11)	0.0255 (12)	0.0053 (10)
C8	0.0664 (16)	0.0365 (14)	0.0415 (13)	0.0211 (11)	0.0271 (12)	0.0061 (11)
N2	0.0400 (9)	0.0293 (10)	0.0302 (9)	0.0128 (7)	0.0085 (7)	0.0043 (7)
C9	0.0453 (12)	0.0363 (13)	0.0319 (11)	0.0186 (10)	0.0064 (9)	0.0033 (9)
C10	0.0437 (12)	0.0403 (13)	0.0323 (11)	0.0198 (10)	0.0117 (9)	0.0034 (10)
N3	0.0365 (9)	0.0358 (11)	0.0327 (10)	0.0151 (8)	0.0049 (7)	0.0008 (8)
C11	0.0371 (11)	0.0359 (12)	0.0329 (11)	0.0138 (9)	0.0086 (9)	0.0051 (9)
C12	0.0457 (12)	0.0333 (12)	0.0289 (11)	0.0169 (9)	0.0088 (9)	0.0050 (9)
C13	0.0400 (11)	0.0277 (11)	0.0313 (11)	0.0148 (9)	0.0026 (9)	0.0064 (9)
C14	0.0337 (11)	0.0425 (14)	0.0389 (12)	0.0129 (9)	0.0066 (9)	0.0007 (10)
C15	0.0382 (12)	0.0495 (15)	0.0356 (12)	0.0177 (10)	0.0084 (9)	−0.0034 (10)
S3	0.0443 (3)	0.0374 (3)	0.0313 (3)	0.0071 (2)	0.0037 (2)	0.0024 (2)
S4	0.0408 (3)	0.0383 (3)	0.0477 (3)	0.0154 (2)	0.0009 (2)	0.0144 (3)
C16	0.0394 (11)	0.0294 (12)	0.0305 (11)	0.0140 (9)	0.0036 (9)	0.0038 (9)
C17	0.0320 (11)	0.0377 (13)	0.0421 (13)	0.0129 (9)	0.0085 (9)	0.0107 (10)
C18	0.0376 (11)	0.0454 (14)	0.0421 (13)	0.0218 (10)	0.0088 (10)	0.0140 (11)
N4	0.0365 (9)	0.0342 (10)	0.0350 (10)	0.0136 (8)	0.0084 (8)	0.0078 (8)
C19	0.0312 (10)	0.0495 (15)	0.0341 (12)	0.0149 (10)	0.0062 (9)	0.0055 (10)
C20	0.0348 (11)	0.0452 (14)	0.0362 (12)	0.0203 (10)	0.0035 (9)	0.0070 (10)
O1	0.0494 (9)	0.0504 (10)	0.0324 (8)	0.0286 (8)	0.0101 (7)	0.0016 (7)
O2	0.0647 (11)	0.0735 (13)	0.0402 (10)	0.0405 (10)	0.0204 (8)	0.0146 (9)
C21	0.0413 (12)	0.0386 (13)	0.0377 (12)	0.0171 (10)	0.0113 (10)	0.0019 (10)
C22	0.092 (2)	0.087 (2)	0.0610 (18)	0.0650 (19)	0.0367 (17)	0.0286 (16)
C23	0.0567 (15)	0.0557 (17)	0.0517 (15)	0.0366 (13)	0.0176 (12)	0.0113 (13)
C24	0.0659 (18)	0.060 (2)	0.073 (2)	0.0278 (15)	0.0109 (15)	0.0058 (16)
C25	0.103 (3)	0.067 (2)	0.111 (3)	0.048 (2)	0.043 (3)	0.041 (2)
C26	0.134 (4)	0.133 (4)	0.068 (2)	0.102 (3)	0.028 (3)	0.033 (3)
C27	0.093 (3)	0.123 (4)	0.065 (2)	0.068 (3)	−0.0098 (19)	−0.012 (2)
C28	0.0663 (18)	0.060 (2)	0.081 (2)	0.0295 (15)	0.0121 (16)	−0.0011 (17)
O3	0.0613 (10)	0.0496 (10)	0.0361 (9)	0.0325 (8)	0.0156 (8)	0.0069 (8)
O4	0.0900 (15)	0.0695 (15)	0.0499 (12)	0.0298 (11)	0.0025 (10)	−0.0152 (10)
C29	0.0546 (14)	0.0338 (13)	0.0398 (13)	0.0164 (10)	0.0189 (11)	0.0083 (10)
C30	0.080 (2)	0.072 (2)	0.0706 (19)	0.0493 (17)	0.0411 (16)	0.0242 (16)
C31	0.0523 (14)	0.0432 (15)	0.0565 (15)	0.0286 (11)	0.0183 (12)	0.0071 (12)
C32	0.0708 (18)	0.0469 (17)	0.0577 (18)	0.0215 (14)	−0.0027 (14)	−0.0036 (14)
C33	0.086 (2)	0.0390 (17)	0.078 (2)	0.0230 (14)	0.0032 (17)	0.0111 (15)
C34	0.081 (2)	0.075 (2)	0.0628 (19)	0.0527 (18)	0.0094 (16)	0.0146 (17)
C35	0.0722 (19)	0.070 (2)	0.0612 (19)	0.0390 (17)	−0.0052 (15)	−0.0109 (16)
C36	0.0598 (16)	0.0419 (16)	0.075 (2)	0.0192 (12)	0.0097 (14)	−0.0055 (15)
O5	0.0779 (14)	0.0842 (17)	0.0699 (15)	0.0144 (12)	0.0105 (11)	−0.0102 (12)

Geometric parameters (Å, º) top

Zn—O1	2.1105 (15)	C17—C18	1.371 (3)
Zn—N4ⁱ	2.160 (2)	C17—H17A	0.9300
Zn—N1	2.180 (2)	C18—N4	1.338 (3)
Zn—N2ⁱⁱ	2.1808 (19)	C18—H18A	0.9300
Zn—N3	2.186 (2)	N4—C19	1.338 (3)
Zn—O3	2.2019 (16)	N4—Znⁱⁱ	2.160 (2)
N1—C5	1.332 (3)	C19—C20	1.371 (3)
N1—C1	1.333 (3)	C19—H19A	0.9300
C1—C2	1.386 (3)	C20—H20A	0.9300
C1—H1A	0.9300	O1—C21	1.270 (2)
C2—C3	1.383 (3)	O2—C21	1.235 (3)
C2—H2A	0.9300	C21—C22	1.512 (4)
C3—C4	1.385 (3)	C22—C23	1.494 (4)
C3—S1	1.776 (2)	C22—H22A	0.9700
C4—C5	1.381 (3)	C22—H22B	0.9700
C4—H4A	0.9300	C23—C24	1.369 (4)
C5—H5A	0.9300	C23—C28	1.375 (4)
S1—S2	2.0311 (10)	C24—C25	1.387 (5)
S2—C6	1.770 (2)	C24—H24A	0.9300
C6—C7	1.377 (3)	C25—C26	1.351 (6)
C6—C10	1.387 (3)	C25—H25A	0.9300
C7—C8	1.381 (3)	C26—C27	1.351 (6)
C7—H7A	0.9300	C26—H26A	0.9300
C8—N2	1.324 (3)	C27—C28	1.376 (5)
C8—H8A	0.9300	C27—H27A	0.9300
N2—C9	1.343 (3)	C28—H28A	0.9300
N2—Znⁱ	2.1808 (19)	O3—C29	1.251 (3)
C9—C10	1.376 (3)	O4—C29	1.242 (3)
C9—H9A	0.9300	C29—C30	1.528 (4)
C10—H10A	0.9300	C30—C31	1.504 (4)
N3—C15	1.335 (3)	C30—H30A	0.9700
N3—C11	1.341 (3)	C30—H30B	0.9700
C11—C12	1.375 (3)	C31—C36	1.379 (4)
C11—H11A	0.9300	C31—C32	1.380 (4)
C12—C13	1.387 (3)	C32—C33	1.373 (4)
C12—H12A	0.9300	C32—H32A	0.9300
C13—C14	1.387 (3)	C33—C34	1.372 (4)
C13—S3	1.773 (2)	C33—H33A	0.9300
C14—C15	1.376 (3)	C34—C35	1.357 (4)
C14—H14A	0.9300	C34—H34A	0.9300
C15—H15A	0.9300	C35—C36	1.379 (4)
S3—S4	2.0294 (10)	C35—H35A	0.9300
S4—C16	1.764 (2)	C36—H36A	0.9300
C16—C17	1.382 (3)	O5—H5C	0.8098
C16—C20	1.392 (3)	O5—H5D	0.8029

O1—Zn—N4ⁱ	97.17 (7)	C17—C16—S4	126.14 (17)
O1—Zn—N1	87.04 (7)	C20—C16—S4	115.38 (17)
N4ⁱ—Zn—N1	88.63 (7)	C18—C17—C16	118.5 (2)
O1—Zn—N2ⁱⁱ	88.99 (7)	C18—C17—H17A	120.7
N4ⁱ—Zn—N2ⁱⁱ	173.74 (7)	C16—C17—H17A	120.7
N1—Zn—N2ⁱⁱ	90.57 (7)	N4—C18—C17	124.0 (2)
O1—Zn—N3	88.99 (7)	N4—C18—H18A	118.0
N4ⁱ—Zn—N3	92.71 (7)	C17—C18—H18A	118.0
N1—Zn—N3	175.94 (7)	C19—N4—C18	116.7 (2)
N2ⁱⁱ—Zn—N3	88.51 (7)	C19—N4—Znⁱⁱ	119.65 (14)
O1—Zn—O3	174.45 (6)	C18—N4—Znⁱⁱ	122.96 (15)
N4ⁱ—Zn—O3	84.12 (7)	N4—C19—C20	123.7 (2)
N1—Zn—O3	98.39 (7)	N4—C19—H19A	118.2
N2ⁱⁱ—Zn—O3	89.85 (7)	C20—C19—H19A	118.2
N3—Zn—O3	85.56 (7)	C19—C20—C16	118.6 (2)
C5—N1—C1	117.18 (19)	C19—C20—H20A	120.7
C5—N1—Zn	122.60 (15)	C16—C20—H20A	120.7
C1—N1—Zn	119.88 (15)	C21—O1—Zn	137.60 (16)
N1—C1—C2	123.3 (2)	O2—C21—O1	126.2 (2)
N1—C1—H1A	118.4	O2—C21—C22	116.3 (2)
C2—C1—H1A	118.4	O1—C21—C22	117.5 (2)
C3—C2—C1	118.7 (2)	C23—C22—C21	117.5 (2)
C3—C2—H2A	120.6	C23—C22—H22A	107.9
C1—C2—H2A	120.6	C21—C22—H22A	107.9
C2—C3—C4	118.5 (2)	C23—C22—H22B	107.9
C2—C3—S1	116.61 (17)	C21—C22—H22B	107.9
C4—C3—S1	124.88 (18)	H22A—C22—H22B	107.2
C5—C4—C3	118.4 (2)	C24—C23—C28	116.9 (3)
C5—C4—H4A	120.8	C24—C23—C22	121.5 (3)
C3—C4—H4A	120.8	C28—C23—C22	121.6 (3)
N1—C5—C4	123.9 (2)	C23—C24—C25	121.4 (3)
N1—C5—H5A	118.1	C23—C24—H24A	119.3
C4—C5—H5A	118.1	C25—C24—H24A	119.3
C3—S1—S2	104.60 (9)	C26—C25—C24	119.9 (4)
C6—S2—S1	105.51 (8)	C26—C25—H25A	120.1
C7—C6—C10	118.0 (2)	C24—C25—H25A	120.1
C7—C6—S2	125.76 (19)	C25—C26—C27	120.2 (4)
C10—C6—S2	116.21 (16)	C25—C26—H26A	119.9
C6—C7—C8	119.0 (2)	C27—C26—H26A	119.9
C6—C7—H7A	120.5	C26—C27—C28	119.8 (4)
C8—C7—H7A	120.5	C26—C27—H27A	120.1
N2—C8—C7	123.7 (2)	C28—C27—H27A	120.1
N2—C8—H8A	118.2	C23—C28—C27	121.9 (3)
C7—C8—H8A	118.2	C23—C28—H28A	119.1
C8—N2—C9	117.00 (19)	C27—C28—H28A	119.1
C8—N2—Znⁱ	121.68 (14)	C29—O3—Zn	143.09 (17)
C9—N2—Znⁱ	120.90 (15)	O4—C29—O3	125.0 (2)
N2—C9—C10	123.3 (2)	O4—C29—C30	117.4 (2)
N2—C9—H9A	118.4	O3—C29—C30	117.5 (2)
C10—C9—H9A	118.4	C31—C30—C29	117.2 (2)
C9—C10—C6	118.9 (2)	C31—C30—H30A	108.0
C9—C10—H10A	120.5	C29—C30—H30A	108.0
C6—C10—H10A	120.5	C31—C30—H30B	108.0
C15—N3—C11	117.28 (19)	C29—C30—H30B	108.0
C15—N3—Zn	122.71 (14)	H30A—C30—H30B	107.3
C11—N3—Zn	119.66 (14)	C36—C31—C32	117.1 (3)
N3—C11—C12	123.3 (2)	C36—C31—C30	122.5 (3)
N3—C11—H11A	118.4	C32—C31—C30	120.3 (3)
C12—C11—H11A	118.4	C33—C32—C31	121.7 (3)
C11—C12—C13	118.72 (19)	C33—C32—H32A	119.2
C11—C12—H12A	120.6	C31—C32—H32A	119.2
C13—C12—H12A	120.6	C34—C33—C32	120.3 (3)
C14—C13—C12	118.5 (2)	C34—C33—H33A	119.9
C14—C13—S3	125.30 (17)	C32—C33—H33A	119.9
C12—C13—S3	116.18 (16)	C35—C34—C33	118.9 (3)
C15—C14—C13	118.6 (2)	C35—C34—H34A	120.6
C15—C14—H14A	120.7	C33—C34—H34A	120.6
C13—C14—H14A	120.7	C34—C35—C36	120.9 (3)
N3—C15—C14	123.5 (2)	C34—C35—H35A	119.5
N3—C15—H15A	118.2	C36—C35—H35A	119.5
C14—C15—H15A	118.2	C31—C36—C35	121.1 (3)
C13—S3—S4	105.43 (8)	C31—C36—H36A	119.5
C16—S4—S3	106.12 (8)	C35—C36—H36A	119.5
C17—C16—C20	118.5 (2)	H5C—O5—H5D	95.1

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5c···O4ⁱⁱⁱ	0.81	2.20	2.970 (3)	158
O5—H5d···O4	0.80	2.15	2.945 (3)	169

Symmetry code: (iii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₇O₂)₂(C₁₀H₈N₂S₂)₂]·H₂O
M_r	794.27
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.851 (2), 11.130 (2), 18.319 (4)
α, β, γ (°)	90.38 (3), 98.88 (3), 115.89 (3)
V (Å³)	1779.0 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.51 × 0.41 × 0.36

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.623, 0.701
No. of measured, independent and observed [I > 2σ(I)] reflections	16701, 7859, 6036
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.092, 1.07
No. of reflections	7859
No. of parameters	451
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.34

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).