Aqua­(2,2′-diamino-4,4′-bi-1,3-thia­zole-κ2N3,N3′)(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)zinc tetra­hydrate

Wang, Y.-L.; Chang, G.-J.; Liu, B.-X.

doi:10.1107/S1600536811015145

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m683-m684

doi:10.1107/S1600536811015145

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Aqua(2,2′-diamino-4,4′-bi-1,3-thiazole-κ²N³,N^3′)(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)zinc tetrahydrate

Yan-Li Wang,^a Guang-Jun Chang ^a and Bing-Xin Liu ^a ^*

^aDepartment of Chemistry, Shanghai University, People's Republic of China
^*Correspondence e-mail: r5744011@yahoo.com.cn

(Received 6 April 2011; accepted 21 April 2011; online 7 May 2011)

The title compound, [Zn(C₇H₃NO₄)(C₆H₆N₄S₂)(H₂O)]·4H₂O, assumes a distorted octahedral coordination geometry around the Zn²⁺ cation, formed by a diaminobithiazole (DABT) molecule, a pyridine-2,6-dicarboxylate anion and a water molecule. The pyridine-2,6-dicarboxylate anion chelates to the Zn^II atom with a facial configuration. Within the chelating DABT ligand, the two thiazole rings are twisted by a dihedral angle of 14.52 (8)° with respect to each other. O—H⋯O and N—H⋯O hydrogen bonds occur in the crystal structure.

Related literature

For potential applications of transition metal complexes of 2,2′-diamino-4,4′-bi-1,3-thiazole (DABT), see: Sun et al. (1997 ). For general background to metal complexes with DABT, see: Liu et al. (2003 ). For related structures, see: Liu & Xu (2004 , 2005 ); Liu et al. (2005 ).

Experimental

Crystal data

[Zn(C₇H₃NO₄)(C₆H₆N₄S₂)(H₂O)]·4H₂O
M_r = 518.82
Monoclinic, P 2₁ /c
a = 10.0529 (19) Å
b = 7.0833 (13) Å
c = 27.720 (6) Å
β = 93.960 (3)°
V = 1969.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.52 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.701, T_max = 0.796
9851 measured reflections
3471 independent reflections
2238 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.119
S = 1.03
3471 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn—N21	2.064 (4)
Zn—N11	2.092 (4)
Zn—N13	2.129 (4)
Zn—O1	2.213 (3)
Zn—O23	2.232 (4)
Zn—O21	2.260 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O22ⁱ	0.97	1.84	2.778 (5)	163
O1—H1B⋯O1W	0.96	1.87	2.827 (6)	174
O1W—H1WA⋯O4Wⁱⁱ	0.91	2.10	2.812 (6)	134
O1W—H1WB⋯O2Wⁱ	0.80	2.10	2.775 (6)	142
O2W—H2WA⋯O22	0.82	1.93	2.692 (6)	155
O2W—H2WB⋯O4Wⁱⁱⁱ	0.86	1.97	2.830 (6)	178
O3W—H3WA⋯O24	0.94	1.94	2.880 (6)	174
O3W—H3WB⋯O24^iv	0.96	1.80	2.694 (6)	153
O4W—H4WA⋯O2Wⁱⁱ	0.91	2.02	2.863 (6)	153
O4W—H4WB⋯O3W	0.88	1.92	2.783 (6)	167
N12—H12A⋯O1	0.97	2.00	2.873 (6)	149
N12—H12B⋯O21^v	0.83	2.19	2.984 (5)	161
N14—H14A⋯O3W^vi	0.88	2.44	3.043 (6)	126
N14—H14B⋯O1W^vii	0.86	2.19	3.022 (6)	162
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) x, y+1, z; (iv) -x+2, -y, -z+1; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) -x+2, -y+1, -z+1; (vii) x+1, y, z.

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015145/ff2006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015145/ff2006Isup2.hkl

checkCIF report

Comment top

Transition metal complexes of 2,2'-diamino-4,4'-bi-1,3-thiazole (DABT) have shown potential application in the field of soft magnetic material (Sun et al., 1997). As part of serial structural investigation of metal complexes with DABT (Liu et al., 2003), the title Zn^II complex was recently prepared and its X-ray structure is presented here.

The molecular structure of the title compound is shown in Fig. 1. The complex has a distorted octahedral coordinatation geometry formed by a DABT ligand, a pyridine-2,6-dicarboxylate anion and a coordinated water molecule.

Thiazole rings of DABT are not coplanar as same as in other complexes we have reported, the dihedral angle between the two thiazole rings is 14.51 (8) °. It is similar to the 17.23 (7) ° found in [Cr(C₄H₅NO₄)(C₆H₆N₄S₂)(H₂O)]Cl^.H₂O, (Liu & Xu, 2004). The distances of C16—N14 [1.335 (4) Å] and C16—N13[1.324 (4) Å] imply the existence of electron delocalization between thiazole rings and amino groups. This feature of electron delocalization of DABT can be found in some DABT complexes of Mn(II) (Liu & Xu, 2005), Co(II) (Liu et al., 2005), we have reported. The tridentate pyridine-2,6-dicarboxylate anion chelates to the Zn^II atom with a facial configuration with the maximum atomic deviation of 0.082 (3) Å (N21) to the main plane defined by C21 C22 C23 C24 C25 C26 C27 N21 O21 O22 O23 O24.

The extensive hydrogen bonding between lattice water molecules, complex and lattice water helps to stabilize the crystal structure as shown in Fig. 2. and Table 1.

Related literature top

For potential applications of transition metal complexes of 2,2'-diamino-4,4'-bi-1,3-thiazole (DABT), see Sun et al. (1997). For general background to metal complexes with DABT, see Liu et al. (2003). For related structures, see: Liu & Xu (2004, 2005); Liu et al. (2005).

Experimental top

An aqueous solution (20 ml) containing DABT (1 mmol) and ZnCl₂ (1 mmol) was mixed with an aqueous solution (10 ml) of pyridine-2,6-dicarboxylic acid (1 mmol) and NaOH (2 mmol). The mixture was refluxed for 5 h. After cooling to room temperature the solution was filtered. Single crystals of (I) were obtained from the filtrate after 10 d.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms), dashed lines showing the hydrogen bonding within the complex.
	Fig. 2. The hydrogen bonding diagram with 30% probability displacement ellipsoids (arbitrary spheres for H atoms), dashed lines indicate the hydrogen bonding.

Aqua(2,2'-diamino-4,4'-bi-1,3-thiazole-κ²N³,N^3')(pyridine- 2,6-dicarboxylato-κ³O²,N,O⁶)zinc tetrahydrate top

Crystal data top

[Zn(C₇H₃NO₄)(C₆H₆N₄S₂)(H₂O)]·4H₂O	F(000) = 1064
M_r = 518.82	D_x = 1.750 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3380 reflections
a = 10.0529 (19) Å	θ = 2.0–25.0°
b = 7.0833 (13) Å	µ = 1.52 mm⁻¹
c = 27.720 (6) Å	T = 295 K
β = 93.960 (3)°	Prism, yellow
V = 1969.2 (7) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3471 independent reflections
Radiation source: fine-focus sealed tube	2238 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→8
T_min = 0.701, T_max = 0.796	l = −22→32
9851 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0374P)² + 1.648P] where P = (F_o² + 2F_c²)/3
3471 reflections	(Δ/σ)_max < 0.001
281 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

[Zn(C₇H₃NO₄)(C₆H₆N₄S₂)(H₂O)]·4H₂O	V = 1969.2 (7) Å³
M_r = 518.82	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0529 (19) Å	µ = 1.52 mm⁻¹
b = 7.0833 (13) Å	T = 295 K
c = 27.720 (6) Å	0.25 × 0.20 × 0.15 mm
β = 93.960 (3)°

Data collection top

Bruker SMART APEX diffractometer	3471 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2238 reflections with I > 2σ(I)
T_min = 0.701, T_max = 0.796	R_int = 0.074
9851 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.40 e Å⁻³
3471 reflections	Δρ_min = −0.60 e Å⁻³
281 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
Zn	0.79367 (6)	0.53096 (9)	0.32687 (2)	0.0278 (2)
O1	0.6001 (3)	0.3881 (5)	0.33361 (13)	0.0323 (9)
H1A	0.6206	0.2602	0.3443	0.031 (15)*
H1B	0.5456	0.4465	0.3567	0.06 (2)*
O21	0.6938 (3)	0.8166 (5)	0.32814 (13)	0.0322 (9)
O22	0.6230 (4)	1.0365 (5)	0.37777 (13)	0.0352 (9)
O23	0.8776 (4)	0.2804 (5)	0.36725 (13)	0.0330 (9)
O24	0.9366 (4)	0.1804 (6)	0.44238 (14)	0.0460 (11)
N11	0.7611 (4)	0.5270 (6)	0.25153 (14)	0.0249 (10)
N12	0.5302 (4)	0.4822 (7)	0.23428 (16)	0.0401 (13)
H12A	0.5190	0.4432	0.2673	0.048*
H12B	0.4789	0.4457	0.2116	0.048*
N13	0.9917 (4)	0.5795 (6)	0.30709 (15)	0.0270 (11)
N14	1.1350 (4)	0.5784 (7)	0.37784 (17)	0.0434 (13)
H14A	1.0773	0.6054	0.3991	0.052*
H14B	1.2189	0.5943	0.3857	0.052*
N21	0.7907 (4)	0.6039 (6)	0.39887 (15)	0.0238 (10)
S11	0.68935 (14)	0.5508 (2)	0.16108 (5)	0.0368 (4)
S12	1.23955 (13)	0.5564 (2)	0.29119 (5)	0.0348 (4)
C11	0.8759 (5)	0.5611 (7)	0.22697 (18)	0.0250 (12)
C12	0.8558 (5)	0.5786 (8)	0.1793 (2)	0.0333 (14)
H12	0.9225	0.6026	0.1585	0.040*
C13	0.6547 (5)	0.5153 (7)	0.22092 (18)	0.0265 (12)
C14	1.0006 (5)	0.5681 (7)	0.25667 (19)	0.0255 (12)
C15	1.1253 (5)	0.5557 (8)	0.2422 (2)	0.0323 (13)
H15	1.1467	0.5478	0.2102	0.039*
C16	1.1095 (5)	0.5723 (8)	0.3291 (2)	0.0306 (13)
C21	0.7370 (5)	0.7687 (7)	0.41205 (18)	0.0243 (12)
C22	0.7300 (6)	0.8163 (8)	0.45964 (19)	0.0348 (14)
H22	0.6938	0.9313	0.4682	0.042*
C23	0.7783 (6)	0.6894 (8)	0.4950 (2)	0.0364 (14)
H23	0.7755	0.7193	0.5276	0.044*
C24	0.8303 (5)	0.5195 (7)	0.4814 (2)	0.0324 (14)
H24	0.8614	0.4324	0.5046	0.039*
C25	0.8355 (5)	0.4801 (7)	0.43272 (19)	0.0270 (12)
C26	0.6810 (5)	0.8848 (8)	0.3697 (2)	0.0287 (13)
C27	0.8889 (5)	0.2973 (7)	0.4127 (2)	0.0298 (13)
O1W	0.4314 (4)	0.5366 (7)	0.40173 (16)	0.0453 (11)
H1WA	0.4454	0.6614	0.4085	0.06 (2)*
H1WB	0.4538	0.4785	0.4256	0.08 (3)*
O2W	0.5018 (4)	1.2043 (6)	0.45001 (16)	0.0533 (12)
H2WA	0.5563	1.1778	0.4303	0.06 (2)*
H2WB	0.5413	1.1846	0.4782	0.05 (2)*
O3W	0.9102 (4)	0.1298 (5)	0.54438 (17)	0.0485 (12)
H3WA	0.9229	0.1380	0.5111	0.11 (3)*
H3WB	0.9730	0.0390	0.5580	0.051 (18)*
O4W	0.6334 (4)	0.1492 (6)	0.54252 (14)	0.0465 (11)
H4WA	0.6074	0.0351	0.5539	0.14 (4)*
H4WB	0.7192	0.1338	0.5388	0.05 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.0276 (4)	0.0333 (4)	0.0226 (4)	0.0023 (3)	0.0028 (3)	0.0000 (3)
O1	0.034 (2)	0.032 (2)	0.031 (2)	0.0021 (18)	0.0031 (18)	0.0038 (18)
O21	0.034 (2)	0.040 (2)	0.022 (2)	0.0082 (18)	−0.0013 (17)	0.0010 (18)
O22	0.045 (2)	0.024 (2)	0.037 (2)	0.0128 (19)	0.0054 (19)	0.0033 (18)
O23	0.037 (2)	0.028 (2)	0.035 (2)	0.0057 (17)	0.0031 (19)	−0.0012 (18)
O24	0.065 (3)	0.033 (2)	0.040 (3)	0.022 (2)	0.004 (2)	0.005 (2)
N11	0.025 (2)	0.027 (3)	0.022 (2)	0.001 (2)	0.0027 (19)	0.003 (2)
N12	0.030 (3)	0.065 (4)	0.024 (3)	0.000 (3)	−0.003 (2)	0.001 (2)
N13	0.022 (2)	0.031 (3)	0.028 (3)	−0.0009 (19)	0.003 (2)	0.000 (2)
N14	0.023 (3)	0.073 (4)	0.035 (3)	−0.003 (2)	0.004 (2)	−0.002 (3)
N21	0.021 (2)	0.026 (3)	0.024 (3)	0.0024 (19)	0.0020 (19)	0.000 (2)
S11	0.0403 (9)	0.0476 (10)	0.0221 (8)	0.0015 (7)	−0.0013 (6)	0.0025 (7)
S12	0.0238 (7)	0.0401 (9)	0.0412 (9)	0.0012 (6)	0.0064 (7)	0.0010 (7)
C11	0.026 (3)	0.025 (3)	0.024 (3)	0.000 (2)	0.002 (2)	−0.005 (2)
C12	0.036 (3)	0.038 (4)	0.027 (3)	−0.002 (3)	0.008 (3)	0.002 (3)
C13	0.028 (3)	0.029 (3)	0.023 (3)	0.006 (2)	0.002 (2)	−0.007 (2)
C14	0.031 (3)	0.021 (3)	0.025 (3)	0.003 (2)	0.004 (2)	−0.002 (2)
C15	0.036 (3)	0.035 (3)	0.027 (3)	0.000 (3)	0.011 (3)	0.003 (3)
C16	0.030 (3)	0.033 (3)	0.030 (3)	−0.001 (3)	0.004 (3)	0.001 (3)
C21	0.027 (3)	0.024 (3)	0.022 (3)	0.000 (2)	0.002 (2)	−0.001 (2)
C22	0.044 (4)	0.031 (3)	0.029 (3)	0.013 (3)	0.004 (3)	−0.003 (3)
C23	0.046 (4)	0.043 (4)	0.020 (3)	0.006 (3)	0.007 (3)	−0.001 (3)
C24	0.044 (3)	0.026 (3)	0.027 (3)	0.011 (3)	0.003 (3)	0.006 (3)
C25	0.027 (3)	0.025 (3)	0.029 (3)	0.000 (2)	0.004 (2)	0.006 (3)
C26	0.027 (3)	0.027 (3)	0.032 (4)	−0.006 (3)	0.003 (3)	−0.003 (3)
C27	0.034 (3)	0.019 (3)	0.038 (4)	0.001 (2)	0.006 (3)	0.002 (3)
O1W	0.045 (3)	0.046 (3)	0.044 (3)	0.007 (2)	0.001 (2)	−0.001 (2)
O2W	0.059 (3)	0.067 (3)	0.035 (3)	0.023 (2)	0.010 (3)	0.010 (2)
O3W	0.054 (3)	0.040 (3)	0.052 (3)	0.021 (2)	0.008 (2)	0.006 (2)
O4W	0.050 (3)	0.050 (3)	0.040 (3)	0.004 (2)	0.006 (2)	−0.002 (2)

Geometric parameters (Å, º) top

Zn—N21	2.064 (4)	S11—C13	1.737 (5)
Zn—N11	2.092 (4)	S12—C15	1.717 (6)
Zn—N13	2.129 (4)	S12—C16	1.736 (5)
Zn—O1	2.213 (3)	C11—C12	1.328 (7)
Zn—O23	2.232 (4)	C11—C14	1.452 (7)
Zn—O21	2.260 (4)	C12—H12	0.9300
O1—H1A	0.9713	C14—C15	1.346 (7)
O1—H1B	0.9633	C15—H15	0.9300
O21—C26	1.264 (6)	C21—C22	1.368 (7)
O22—C26	1.250 (6)	C21—C26	1.510 (7)
O23—C27	1.264 (6)	C22—C23	1.393 (7)
O24—C27	1.239 (6)	C22—H22	0.9300
N11—C13	1.321 (6)	C23—C24	1.375 (7)
N11—C11	1.401 (6)	C23—H23	0.9300
N12—C13	1.351 (6)	C24—C25	1.382 (7)
N12—H12A	0.9708	C24—H24	0.9300
N12—H12B	0.8256	C25—C27	1.521 (7)
N13—C16	1.294 (7)	O1W—H1WA	0.9122
N13—C14	1.409 (6)	O1W—H1WB	0.7978
N14—C16	1.359 (7)	O2W—H2WA	0.8216
N14—H14A	0.8749	O2W—H2WB	0.8624
N14—H14B	0.8645	O3W—H3WA	0.9418
N21—C25	1.339 (6)	O3W—H3WB	0.9604
N21—C21	1.347 (6)	O4W—H4WA	0.9116
S11—C12	1.725 (6)	O4W—H4WB	0.8825

N21—Zn—N11	163.19 (16)	C11—C12—S11	111.1 (4)
N21—Zn—N13	106.55 (16)	C11—C12—H12	124.5
N11—Zn—N13	80.18 (16)	S11—C12—H12	124.5
N21—Zn—O1	87.78 (14)	N11—C13—N12	124.0 (5)
N11—Zn—O1	90.03 (15)	N11—C13—S11	113.4 (4)
N13—Zn—O1	159.90 (15)	N12—C13—S11	122.5 (4)
N21—Zn—O23	75.18 (15)	C15—C14—N13	115.0 (5)
N11—Zn—O23	121.17 (15)	C15—C14—C11	127.9 (5)
N13—Zn—O23	85.97 (15)	N13—C14—C11	117.0 (4)
O1—Zn—O23	84.17 (13)	C14—C15—S12	110.5 (4)
N21—Zn—O21	74.03 (14)	C14—C15—H15	124.7
N11—Zn—O21	89.34 (14)	S12—C15—H15	124.7
N13—Zn—O21	106.47 (15)	N13—C16—N14	124.8 (5)
O1—Zn—O21	90.79 (14)	N13—C16—S12	114.8 (4)
O23—Zn—O21	148.96 (13)	N14—C16—S12	120.4 (4)
Zn—O1—H1A	106.4	N21—C21—C22	121.6 (5)
Zn—O1—H1B	113.8	N21—C21—C26	113.3 (4)
H1A—O1—H1B	108.5	C22—C21—C26	125.0 (5)
C26—O21—Zn	115.4 (3)	C21—C22—C23	118.7 (5)
C27—O23—Zn	115.5 (3)	C21—C22—H22	120.6
C13—N11—C11	110.9 (4)	C23—C22—H22	120.6
C13—N11—Zn	134.9 (3)	C24—C23—C22	119.5 (5)
C11—N11—Zn	113.9 (3)	C24—C23—H23	120.3
C13—N12—H12A	118.5	C22—C23—H23	120.3
C13—N12—H12B	112.8	C23—C24—C25	119.1 (5)
H12A—N12—H12B	121.5	C23—C24—H24	120.5
C16—N13—C14	110.3 (4)	C25—C24—H24	120.5
C16—N13—Zn	135.5 (4)	N21—C25—C24	121.2 (5)
C14—N13—Zn	111.7 (3)	N21—C25—C27	114.3 (5)
C16—N14—H14A	126.0	C24—C25—C27	124.5 (5)
C16—N14—H14B	111.6	O22—C26—O21	124.7 (5)
H14A—N14—H14B	118.9	O22—C26—C21	118.9 (5)
C25—N21—C21	119.9 (4)	O21—C26—C21	116.4 (5)
C25—N21—Zn	119.2 (3)	O24—C27—O23	127.1 (5)
C21—N21—Zn	120.8 (3)	O24—C27—C25	117.2 (5)
C12—S11—C13	89.5 (3)	O23—C27—C25	115.7 (5)
C15—S12—C16	89.3 (3)	H1WA—O1W—H1WB	107.4
C12—C11—N11	115.2 (5)	H2WA—O2W—H2WB	106.1
C12—C11—C14	128.9 (5)	H3WA—O3W—H3WB	107.3
N11—C11—C14	116.0 (4)	H4WA—O4W—H4WB	103.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O22ⁱ	0.97	1.84	2.778 (5)	163
O1—H1B···O1W	0.96	1.87	2.827 (6)	174
O1W—H1WA···O4Wⁱⁱ	0.91	2.10	2.812 (6)	134
O1W—H1WB···O2Wⁱ	0.80	2.10	2.775 (6)	142
O2W—H2WA···O22	0.82	1.93	2.692 (6)	155
O2W—H2WB···O4Wⁱⁱⁱ	0.86	1.97	2.830 (6)	178
O3W—H3WA···O24	0.94	1.94	2.880 (6)	174
O3W—H3WB···O24^iv	0.96	1.80	2.694 (6)	153
O4W—H4WA···O2Wⁱⁱ	0.91	2.02	2.863 (6)	153
O4W—H4WB···O3W	0.88	1.92	2.783 (6)	167
N12—H12A···O1	0.97	2.00	2.873 (6)	149
N12—H12B···O21^v	0.83	2.19	2.984 (5)	161
N14—H14A···O3W^vi	0.88	2.44	3.043 (6)	126
N14—H14B···O1W^vii	0.86	2.19	3.022 (6)	162

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

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₃NO₄)(C₆H₆N₄S₂)(H₂O)]·4H₂O
M_r	518.82
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.0529 (19), 7.0833 (13), 27.720 (6)
β (°)	93.960 (3)
V (Å³)	1969.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.52
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.701, 0.796
No. of measured, independent and observed [I > 2σ(I)] reflections	9851, 3471, 2238
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.119, 1.03
No. of reflections	3471
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.60

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Zn—N21	2.064 (4)	Zn—O1	2.213 (3)
Zn—N11	2.092 (4)	Zn—O23	2.232 (4)
Zn—N13	2.129 (4)	Zn—O21	2.260 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O22ⁱ	0.97	1.84	2.778 (5)	163
O1—H1B···O1W	0.96	1.87	2.827 (6)	174
O1W—H1WA···O4Wⁱⁱ	0.91	2.10	2.812 (6)	134
O1W—H1WB···O2Wⁱ	0.80	2.10	2.775 (6)	142
O2W—H2WA···O22	0.82	1.93	2.692 (6)	155
O2W—H2WB···O4Wⁱⁱⁱ	0.86	1.97	2.830 (6)	178
O3W—H3WA···O24	0.94	1.94	2.880 (6)	174
O3W—H3WB···O24^iv	0.96	1.80	2.694 (6)	153
O4W—H4WA···O2Wⁱⁱ	0.91	2.02	2.863 (6)	153
O4W—H4WB···O3W	0.88	1.92	2.783 (6)	167
N12—H12A···O1	0.97	2.00	2.873 (6)	149
N12—H12B···O21^v	0.83	2.19	2.984 (5)	161
N14—H14A···O3W^vi	0.88	2.44	3.043 (6)	126
N14—H14B···O1W^vii	0.86	2.19	3.022 (6)	162

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

Acknowledgements

The project was supported by the Foundation of Shanghai University, China.

References

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