Bis[N′-(2-oxo-1H-indol-3-ylidene)thiophene-2-carbohydrazidato-κ3O,N′,O′]zinc(II) N,N-dimethyl­formide mono­solvate monohydrate

Abdul Halim, S.N.; Ali, H.M.; Ng, S.W.

doi:10.1107/S1600536810039504

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1438

https://doi.org/10.1107/S1600536810039504

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Bis[N′-(2-oxo-1H-indol-3-ylidene)thiophene-2-carbohydrazidato-κ³O,N′,O′]zinc(II) N,N-dimethylformide monosolvate monohydrate

Siti Nadiah Abdul Halim,^a ^* Hapipah Mohd Ali ^a and Seik Weng Ng ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: nadiahhalim@um.edu.my

(Received 19 August 2010; accepted 4 October 2010; online 23 October 2010)

The metal atom of the title compound, [Zn(C₁₃H₈N₃O₂S)₂]·C₃H₇NO·H₂O, is O,N,O′-chelated by two deprotonated Schiff bases and it exists in a distorted octahedral geometry. The N–H groups of the ligands, the carbonyl group of the DMF molecule and uncoordinated water molecule engage in N—H⋯O and O—H⋯O interactions, generating a hydrogen-bonded ribbon that propagates along [110]. One thienyl ring is disordered over two positions in a 1:1 ratio.

Related literature

For the crystal structure of [Zn(C₁₃H₈N₃O₂S)₂]·1.75CH₃OH, see: Rodríguez-Argüelles et al. (2009 ).

Experimental

Crystal data

[Zn(C₁₃H₈N₃O₂S)₂]·C₃H₇NO·H₂O
M_r = 697.05
Triclinic, $[P \overline 1]$
a = 11.5250 (8) Å
b = 12.0656 (8) Å
c = 13.4643 (9) Å
α = 105.913 (1)°
β = 100.531 (1)°
γ = 114.754 (1)°
V = 1537.25 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 293 K
0.22 × 0.16 × 0.08 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.812, T_max = 0.925
13275 measured reflections
6630 independent reflections
3036 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.182
S = 0.98
6630 reflections
432 parameters
77 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.103 (3)
Zn1—O2	2.370 (3)
Zn1—O3	2.043 (3)
Zn1—O4	2.440 (3)
Zn1—N2	2.017 (4)
Zn1—N5	2.022 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1w1⋯O2	0.84 (1)	2.06 (3)	2.859 (5)	158 (6)
O1W—H1w2⋯O5	0.84 (1)	2.31 (8)	2.771 (9)	115 (7)
N3—H3N⋯O1Wⁱ	0.84 (1)	1.98 (1)	2.813 (6)	173 (5)
N6—H6N⋯O4ⁱⁱ	0.84 (1)	2.06 (2)	2.884 (5)	169 (5)
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: https://doi.org/10.1107/S1600536810039504/ci5163sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039504/ci5163Isup2.hkl

checkCIF report

Comment top

Divalent cobalt, nickel, copper and zinc derivatives of Schiff base condensation product of isatin and 2-thienylcarboxylic acid hydrazide have been synthesized, and these are reported along with the crystal structure of the zinc derivative, which crystallizes with 1.75 molecules of methanol. The geometry is described as tetrahedral; however, if two weaker Zn···O interations are considered as bonding, the geometry is, in fact, octahedral (Rodríguez-Argüelles et al., 2009). The other compounds are expected to be chelated by the deprotonated Schiff base in a terdentate manner; for it to chelate, the anion has to rotate about the nitrogen-nitrogen bond. Such a rotation is observed in the present zinc complex, which crystallizes from DMF as a monohydrated monosolvate (Scheme I). The divalent metal atom is O,N,O'-chelated by two deprotonated Schiff base in an octahedral geometry (Fig. 1). The amino group, the carbonyl group of the DMF and the lattice water molecule engage in N–H···O and O–H···O hydrogen bonding interactions to generate a hydrogen-bonded ribbon that propagates along [110]. One thienyl ring is disordered over two positions in a 1:1 ratio.

Related literature top

For the crystal structure of [Zn(C₁₃H₈N₃O₂S)₂].1.75CH₃OH, see: Rodríguez-Argüelles et al. (2009).

Experimental top

The Schiff base was synthesized by condensing isatin and furoylhydrazine according to a literature procedure (Rodríguez-Argüelles et al., 2009). Zinc acetate (1 mmol) and the Schiff base (2 mmol) were heated in ethanol (100 ml) for 5 h; several drops of triethylamine were added. The solvent was removed and the product purified by recrystallization from DMF.

Structure description top

For the crystal structure of [Zn(C₁₃H₈N₃O₂S)₂].1.75CH₃OH, see: Rodríguez-Argüelles et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. Displacement ellipsoid plot (Barbour, 2001) of [Zn(C₁₃H₈N₃O₂S)₂].C₃H₇NO.H₂O at the 50% probability level; H atoms are drawn as spheres of arbitrary radius. The disorder in the thienyl ring is not shown.

Bis[N'-(2-oxo-1H-indol-3-ylidene)thiophene-2-carbohydrazidato- κ³O,N',O']zinc(II) N,N-dimethylformide monosolvate monohydrate top

Crystal data top

[Zn(C₁₃H₈N₃O₂S)₂]·C₃H₇NO·H₂O	Z = 2
M_r = 697.05	F(000) = 716
Triclinic, P1	D_x = 1.506 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.5250 (8) Å	Cell parameters from 2596 reflections
b = 12.0656 (8) Å	θ = 2.6–21.1°
c = 13.4643 (9) Å	µ = 0.99 mm⁻¹
α = 105.913 (1)°	T = 293 K
β = 100.531 (1)°	Plate, yellow
γ = 114.754 (1)°	0.22 × 0.16 × 0.08 mm
V = 1537.25 (18) Å³

Data collection top

Bruker SMART area-detector diffractometer	6630 independent reflections
Radiation source: fine-focus sealed tube	3036 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.812, T_max = 0.925	k = −15→15
13275 measured reflections	l = −17→17

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0886P)²] where P = (F_o² + 2F_c²)/3
6630 reflections	(Δ/σ)_max = 0.001
432 parameters	Δρ_max = 0.56 e Å⁻³
77 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Zn(C₁₃H₈N₃O₂S)₂]·C₃H₇NO·H₂O	γ = 114.754 (1)°
M_r = 697.05	V = 1537.25 (18) Å³
Triclinic, P1	Z = 2
a = 11.5250 (8) Å	Mo Kα radiation
b = 12.0656 (8) Å	µ = 0.99 mm⁻¹
c = 13.4643 (9) Å	T = 293 K
α = 105.913 (1)°	0.22 × 0.16 × 0.08 mm
β = 100.531 (1)°

Data collection top

Bruker SMART area-detector diffractometer	6630 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3036 reflections with I > 2σ(I)
T_min = 0.812, T_max = 0.925	R_int = 0.044
13275 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	77 restraints
wR(F²) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.56 e Å⁻³
6630 reflections	Δρ_min = −0.35 e Å⁻³
432 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.50562 (6)	0.34927 (6)	0.74919 (5)	0.0638 (3)
S1	0.91009 (13)	0.79052 (15)	1.01272 (12)	0.0733 (4)
S2	0.6067 (6)	0.0742 (6)	0.9286 (3)	0.1011 (11)	0.50
C14	0.6512 (13)	−0.0461 (12)	0.9100 (13)	0.100 (4)	0.50
H14	0.6557	−0.0852	0.9602	0.120*	0.50
C15	0.6802 (16)	−0.0815 (17)	0.8139 (11)	0.079 (3)	0.50
H15	0.7059	−0.1449	0.7903	0.095*	0.50
C16	0.6622 (12)	−0.0003 (13)	0.7586 (16)	0.0770 (8)	0.50
H16	0.6759	−0.0058	0.6919	0.092*	0.50
S2'	0.6837 (4)	−0.0034 (4)	0.7590 (5)	0.0770 (8)	0.50
C14'	0.6977 (14)	−0.0544 (14)	0.8662 (9)	0.079 (3)	0.50
H14'	0.7307	−0.1121	0.8699	0.095*	0.50
C15'	0.6541 (17)	0.0001 (16)	0.9468 (15)	0.100 (4)	0.50
H15'	0.6533	−0.0146	1.0110	0.120*	0.50
C16'	0.6114 (16)	0.0819 (19)	0.9129 (10)	0.1011 (11)	0.50
H16'	0.5783	0.1286	0.9546	0.121*	0.50
O1	0.6775 (3)	0.5329 (3)	0.8550 (3)	0.0683 (10)
O2	0.2678 (3)	0.2050 (3)	0.6643 (3)	0.0664 (10)
O3	0.5375 (4)	0.2324 (4)	0.8228 (3)	0.0671 (10)
O4	0.4945 (4)	0.4247 (4)	0.5989 (3)	0.0678 (10)
O5	0.2073 (8)	0.2034 (7)	0.3516 (6)	0.171 (3)
O1W	0.1468 (5)	0.0147 (4)	0.4424 (3)	0.0953 (13)
H1W1	0.184 (7)	0.054 (6)	0.5112 (12)	0.143*
H1W2	0.101 (7)	0.048 (7)	0.421 (5)	0.143*
N1	0.5088 (4)	0.5749 (4)	0.9029 (3)	0.0581 (10)
N2	0.4269 (4)	0.4546 (4)	0.8249 (3)	0.0560 (10)
N3	0.0860 (4)	0.2331 (4)	0.6887 (3)	0.0613 (11)
H3N	0.014 (3)	0.163 (3)	0.648 (3)	0.074*
N4	0.6067 (4)	0.1698 (4)	0.6741 (3)	0.0502 (10)
N5	0.5693 (4)	0.2512 (4)	0.6455 (3)	0.0511 (10)
N6	0.5631 (5)	0.3803 (5)	0.4471 (4)	0.0640 (11)
H6N	0.556 (5)	0.440 (4)	0.431 (4)	0.077*
N7	0.1188 (7)	0.3387 (6)	0.3769 (6)	0.112 (2)
C1	0.9569 (7)	0.9300 (6)	1.1235 (5)	0.0846 (18)
H1	1.0461	0.9988	1.1607	0.102*
C2	0.8526 (7)	0.9290 (6)	1.1500 (5)	0.0799 (17)
H2	0.8608	0.9973	1.2089	0.096*
C3	0.7278 (6)	0.8158 (6)	1.0816 (4)	0.0638 (14)
H3B	0.6448	0.8003	1.0900	0.077*
C4	0.7431 (5)	0.7305 (5)	1.0006 (4)	0.0515 (12)
C5	0.6426 (5)	0.6058 (5)	0.9145 (4)	0.0548 (12)
C6	0.2177 (5)	0.2683 (5)	0.7082 (4)	0.0575 (13)
C7	0.2954 (5)	0.4045 (5)	0.7958 (4)	0.0524 (12)
C8	0.1993 (5)	0.4411 (5)	0.8260 (4)	0.0530 (12)
C9	0.2121 (5)	0.5509 (5)	0.9032 (4)	0.0631 (14)
H9	0.2972	0.6224	0.9490	0.076*
C10	0.0925 (6)	0.5518 (6)	0.9109 (5)	0.0765 (16)
H10	0.0975	0.6246	0.9624	0.092*
C11	−0.0324 (6)	0.4443 (7)	0.8419 (5)	0.0742 (16)
H11	−0.1103	0.4473	0.8477	0.089*
C12	−0.0470 (5)	0.3327 (6)	0.7647 (5)	0.0659 (15)
H12	−0.1322	0.2607	0.7199	0.079*
C13	0.0711 (5)	0.3333 (5)	0.7572 (4)	0.0553 (12)
C17	0.6223 (5)	0.0882 (5)	0.8126 (4)	0.0690 (15)
C18	0.5854 (4)	0.1691 (5)	0.7701 (4)	0.0543 (12)
C19	0.5399 (5)	0.3688 (5)	0.5400 (4)	0.0553 (12)
C20	0.5817 (4)	0.2732 (5)	0.5581 (4)	0.0505 (11)
C21	0.6287 (5)	0.2316 (5)	0.4702 (4)	0.0542 (12)
C22	0.6786 (5)	0.1459 (5)	0.4447 (4)	0.0648 (14)
H22	0.6872	0.1001	0.4884	0.078*
C23	0.7155 (6)	0.1303 (7)	0.3521 (5)	0.0864 (18)
H23	0.7499	0.0733	0.3333	0.104*
C24	0.7022 (7)	0.1980 (7)	0.2870 (5)	0.092 (2)
H24	0.7275	0.1847	0.2249	0.111*
C25	0.6524 (6)	0.2849 (6)	0.3109 (5)	0.0785 (17)
H25	0.6436	0.3303	0.2668	0.094*
C26	0.6166 (5)	0.3001 (5)	0.4041 (4)	0.0630 (14)
C27	0.1813 (11)	0.2814 (11)	0.3207 (9)	0.178 (5)
H27	0.2033	0.3002	0.2619	0.214*
C28	0.1061 (10)	0.3139 (10)	0.4682 (8)	0.179 (4)
H28A	0.1924	0.3332	0.5134	0.268*
H28B	0.0408	0.2223	0.4468	0.268*
H28C	0.0760	0.3689	0.5087	0.268*
C29	0.0861 (11)	0.4222 (11)	0.3410 (10)	0.221 (5)
H29A	0.0275	0.3750	0.2656	0.331*
H29B	0.1677	0.4969	0.3474	0.331*
H29C	0.0405	0.4527	0.3851	0.331*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0637 (4)	0.0688 (4)	0.0754 (5)	0.0417 (4)	0.0338 (3)	0.0303 (4)
S1	0.0478 (8)	0.0769 (10)	0.0803 (10)	0.0253 (8)	0.0194 (7)	0.0208 (8)
S2	0.139 (3)	0.104 (2)	0.073 (2)	0.057 (2)	0.0280 (18)	0.0614 (18)
C14	0.120 (6)	0.100 (9)	0.103 (8)	0.066 (5)	0.024 (5)	0.063 (7)
C15	0.078 (5)	0.083 (6)	0.091 (9)	0.049 (4)	0.012 (6)	0.049 (7)
C16	0.0690 (19)	0.0825 (17)	0.112 (2)	0.0505 (15)	0.0397 (17)	0.0564 (16)
S2'	0.0690 (19)	0.0825 (17)	0.112 (2)	0.0505 (15)	0.0397 (17)	0.0564 (16)
C14'	0.078 (5)	0.083 (6)	0.091 (9)	0.049 (4)	0.012 (6)	0.049 (7)
C15'	0.120 (6)	0.100 (9)	0.103 (8)	0.066 (5)	0.024 (5)	0.063 (7)
C16'	0.139 (3)	0.104 (2)	0.073 (2)	0.057 (2)	0.0280 (18)	0.0614 (18)
O1	0.055 (2)	0.066 (2)	0.076 (2)	0.026 (2)	0.0219 (19)	0.023 (2)
O2	0.055 (2)	0.072 (2)	0.067 (2)	0.030 (2)	0.0222 (18)	0.019 (2)
O3	0.076 (2)	0.082 (3)	0.070 (2)	0.050 (2)	0.038 (2)	0.041 (2)
O4	0.083 (3)	0.083 (3)	0.072 (2)	0.057 (2)	0.039 (2)	0.044 (2)
O5	0.216 (6)	0.118 (4)	0.149 (5)	0.074 (4)	0.018 (4)	0.052 (4)
O1W	0.092 (4)	0.075 (3)	0.076 (3)	0.028 (3)	0.016 (3)	0.002 (2)
N1	0.058 (3)	0.061 (3)	0.062 (3)	0.031 (2)	0.025 (2)	0.027 (2)
N2	0.056 (3)	0.061 (3)	0.052 (2)	0.027 (2)	0.018 (2)	0.028 (2)
N3	0.038 (3)	0.068 (3)	0.058 (3)	0.016 (2)	0.012 (2)	0.019 (2)
N4	0.040 (2)	0.054 (2)	0.064 (3)	0.026 (2)	0.019 (2)	0.030 (2)
N5	0.043 (2)	0.053 (2)	0.060 (3)	0.022 (2)	0.0171 (19)	0.027 (2)
N6	0.070 (3)	0.071 (3)	0.065 (3)	0.035 (3)	0.030 (2)	0.041 (3)
N7	0.107 (4)	0.096 (4)	0.106 (4)	0.029 (3)	0.013 (3)	0.052 (4)
C1	0.070 (4)	0.075 (4)	0.071 (4)	0.019 (3)	0.008 (3)	0.014 (3)
C2	0.092 (5)	0.085 (5)	0.056 (4)	0.045 (4)	0.021 (4)	0.018 (3)
C3	0.066 (4)	0.081 (4)	0.067 (3)	0.044 (3)	0.031 (3)	0.042 (3)
C4	0.054 (3)	0.059 (3)	0.052 (3)	0.033 (3)	0.018 (2)	0.028 (3)
C5	0.052 (3)	0.062 (3)	0.061 (3)	0.030 (3)	0.023 (3)	0.034 (3)
C6	0.048 (3)	0.071 (4)	0.052 (3)	0.025 (3)	0.018 (3)	0.029 (3)
C7	0.039 (3)	0.069 (3)	0.056 (3)	0.025 (3)	0.020 (2)	0.033 (3)
C8	0.042 (3)	0.068 (3)	0.054 (3)	0.026 (3)	0.019 (2)	0.029 (3)
C9	0.053 (3)	0.069 (4)	0.062 (3)	0.027 (3)	0.019 (3)	0.023 (3)
C10	0.077 (4)	0.085 (4)	0.081 (4)	0.048 (4)	0.040 (4)	0.032 (4)
C11	0.058 (4)	0.102 (5)	0.090 (4)	0.049 (4)	0.038 (3)	0.051 (4)
C12	0.040 (3)	0.084 (4)	0.077 (4)	0.026 (3)	0.021 (3)	0.044 (3)
C13	0.046 (3)	0.072 (4)	0.058 (3)	0.030 (3)	0.021 (3)	0.037 (3)
C17	0.050 (3)	0.072 (4)	0.091 (4)	0.028 (3)	0.017 (3)	0.048 (3)
C18	0.035 (3)	0.054 (3)	0.073 (4)	0.019 (2)	0.013 (2)	0.032 (3)
C19	0.051 (3)	0.062 (3)	0.061 (3)	0.027 (3)	0.022 (3)	0.035 (3)
C20	0.044 (3)	0.051 (3)	0.054 (3)	0.019 (2)	0.015 (2)	0.026 (2)
C21	0.046 (3)	0.048 (3)	0.062 (3)	0.017 (2)	0.019 (2)	0.022 (3)
C22	0.058 (3)	0.061 (3)	0.068 (4)	0.027 (3)	0.023 (3)	0.016 (3)
C23	0.073 (4)	0.087 (5)	0.093 (5)	0.040 (4)	0.040 (4)	0.019 (4)
C24	0.090 (5)	0.097 (5)	0.073 (4)	0.035 (4)	0.046 (4)	0.017 (4)
C25	0.077 (4)	0.076 (4)	0.064 (4)	0.019 (3)	0.032 (3)	0.026 (3)
C26	0.052 (3)	0.067 (4)	0.060 (3)	0.020 (3)	0.023 (3)	0.025 (3)
C27	0.180 (8)	0.159 (8)	0.140 (7)	0.033 (6)	0.068 (7)	0.055 (6)
C28	0.154 (7)	0.191 (8)	0.180 (7)	0.049 (6)	0.052 (6)	0.121 (7)
C29	0.174 (9)	0.197 (8)	0.265 (10)	0.071 (7)	−0.002 (6)	0.139 (8)

Geometric parameters (Å, º) top

Zn1—O1	2.103 (3)	N7—C28	1.360 (7)
Zn1—O2	2.370 (3)	N7—C27	1.378 (8)
Zn1—O3	2.043 (3)	N7—C29	1.382 (8)
Zn1—O4	2.440 (3)	C1—C2	1.311 (8)
Zn1—N2	2.017 (4)	C1—H1	0.93
Zn1—N5	2.022 (4)	C2—C3	1.402 (8)
S1—C4	1.705 (5)	C2—H2	0.93
S1—C1	1.708 (6)	C3—C4	1.373 (7)
S2—C17	1.650 (6)	C3—H3B	0.93
S2—C14	1.703 (9)	C4—C5	1.429 (7)
C14—C15	1.394 (10)	C6—C7	1.487 (7)
C14—H14	0.93	C7—C8	1.437 (6)
C15—C16	1.440 (10)	C8—C9	1.372 (7)
C15—H15	0.93	C8—C13	1.401 (7)
C16—C17	1.410 (10)	C9—C10	1.406 (7)
C16—H16	0.93	C9—H9	0.93
S2'—C17	1.627 (6)	C10—C11	1.380 (8)
S2'—C14'	1.724 (9)	C10—H10	0.93
C14'—C15'	1.395 (10)	C11—C12	1.378 (8)
C14'—H14'	0.93	C11—H11	0.93
C15'—C16'	1.413 (10)	C12—C13	1.381 (7)
C15'—H15'	0.93	C12—H12	0.93
C16'—C17	1.397 (10)	C17—C18	1.425 (6)
C16'—H16'	0.93	C19—C20	1.483 (6)
O1—C5	1.267 (5)	C20—C21	1.443 (6)
O2—C6	1.231 (6)	C21—C22	1.376 (7)
O3—C18	1.261 (5)	C21—C26	1.396 (7)
O4—C19	1.230 (5)	C22—C23	1.378 (7)
O5—C27	1.246 (8)	C22—H22	0.93
O1W—H1W1	0.842 (11)	C23—C24	1.381 (8)
O1W—H1W2	0.842 (11)	C23—H23	0.93
N1—N2	1.325 (5)	C24—C25	1.385 (9)
N1—C5	1.394 (6)	C24—H24	0.93
N2—C7	1.304 (6)	C25—C26	1.381 (7)
N3—C6	1.343 (6)	C25—H25	0.93
N3—C13	1.400 (7)	C27—H27	0.93
N3—H3N	0.837 (11)	C28—H28A	0.96
N4—N5	1.341 (5)	C28—H28B	0.96
N4—C18	1.361 (6)	C28—H28C	0.96
N5—C20	1.295 (6)	C29—H29A	0.96
N6—C19	1.357 (6)	C29—H29B	0.96
N6—C26	1.404 (7)	C29—H29C	0.96
N6—H6N	0.837 (11)

N2—Zn1—N5	167.72 (15)	O2—C6—C7	125.4 (4)
N2—Zn1—O3	114.39 (14)	N3—C6—C7	105.6 (5)
N5—Zn1—O3	77.23 (14)	N2—C7—C8	138.3 (5)
N2—Zn1—O1	76.24 (16)	N2—C7—C6	113.8 (4)
N5—Zn1—O1	106.84 (14)	C8—C7—C6	107.9 (4)
O3—Zn1—O1	98.83 (15)	C9—C8—C13	121.1 (5)
N2—Zn1—O2	76.55 (15)	C9—C8—C7	133.6 (5)
N5—Zn1—O2	99.15 (14)	C13—C8—C7	105.4 (4)
O3—Zn1—O2	95.14 (14)	C8—C9—C10	117.8 (5)
O1—Zn1—O2	152.62 (13)	C8—C9—H9	121.1
N2—Zn1—O4	92.75 (13)	C10—C9—H9	121.1
N5—Zn1—O4	75.43 (14)	C11—C10—C9	119.9 (6)
O3—Zn1—O4	152.55 (13)	C11—C10—H10	120.1
O1—Zn1—O4	91.31 (13)	C9—C10—H10	120.1
O2—Zn1—O4	86.90 (12)	C12—C11—C10	123.0 (5)
C4—S1—C1	91.4 (3)	C12—C11—H11	118.5
C17—S2—C14	92.9 (8)	C10—C11—H11	118.5
C15—C14—S2	115.0 (15)	C11—C12—C13	116.7 (5)
C15—C14—H14	122.5	C11—C12—H12	121.6
S2—C14—H14	122.5	C13—C12—H12	121.6
C14—C15—C16	106.1 (19)	C12—C13—N3	128.7 (5)
C14—C15—H15	126.9	C12—C13—C8	121.5 (5)
C16—C15—H15	126.9	N3—C13—C8	109.7 (4)
C17—C16—C15	115.3 (18)	C16'—C17—C16	112.4 (14)
C17—C16—H16	122.3	C16'—C17—C18	121.4 (11)
C15—C16—H16	122.3	C16—C17—C18	126.0 (10)
C17—S2'—C14'	93.3 (8)	C16'—C17—S2'	110.9 (11)
C15'—C14'—S2'	112.7 (15)	C18—C17—S2'	127.6 (4)
C15'—C14'—H14'	123.6	C16—C17—S2	110.6 (10)
S2'—C14'—H14'	123.6	C18—C17—S2	123.1 (5)
C14'—C15'—C16'	107 (2)	S2'—C17—S2	109.3 (4)
C14'—C15'—H15'	126.3	O3—C18—N4	126.4 (4)
C16'—C15'—H15'	126.3	O3—C18—C17	118.7 (5)
C17—C16'—C15'	115.7 (19)	N4—C18—C17	114.9 (5)
C17—C16'—H16'	122.1	O4—C19—N6	128.6 (5)
C15'—C16'—H16'	122.1	O4—C19—C20	125.8 (4)
C5—O1—Zn1	110.2 (3)	N6—C19—C20	105.6 (4)
C6—O2—Zn1	104.5 (3)	N5—C20—C21	137.5 (4)
C18—O3—Zn1	110.5 (3)	N5—C20—C19	114.7 (4)
C19—O4—Zn1	103.2 (3)	C21—C20—C19	107.8 (4)
H1W1—O1W—H1W2	108.7 (19)	C22—C21—C26	120.6 (5)
N2—N1—C5	108.4 (4)	C22—C21—C20	133.6 (5)
C7—N2—N1	120.2 (4)	C26—C21—C20	105.8 (4)
C7—N2—Zn1	119.8 (4)	C21—C22—C23	117.7 (6)
N1—N2—Zn1	120.0 (3)	C21—C22—H22	121.1
C6—N3—C13	111.3 (4)	C23—C22—H22	121.1
C6—N3—H3N	133 (4)	C22—C23—C24	121.1 (6)
C13—N3—H3N	116 (4)	C22—C23—H23	119.4
N5—N4—C18	108.0 (4)	C24—C23—H23	119.4
C20—N5—N4	121.4 (4)	C23—C24—C25	122.3 (6)
C20—N5—Zn1	120.7 (3)	C23—C24—H24	118.8
N4—N5—Zn1	117.8 (3)	C25—C24—H24	118.8
C19—N6—C26	111.1 (4)	C26—C25—C24	116.0 (6)
C19—N6—H6N	117 (4)	C26—C25—H25	122.0
C26—N6—H6N	131 (4)	C24—C25—H25	122.0
C28—N7—C27	115.1 (8)	C25—C26—C21	122.2 (6)
C28—N7—C29	127.0 (10)	C25—C26—N6	128.1 (5)
C27—N7—C29	117.7 (9)	C21—C26—N6	109.7 (4)
C2—C1—S1	112.2 (5)	O5—C27—N7	117.4 (10)
C2—C1—H1	123.9	O5—C27—H27	121.3
S1—C1—H1	123.9	N7—C27—H27	121.3
C1—C2—C3	113.9 (6)	N7—C28—H28A	109.5
C1—C2—H2	123.1	N7—C28—H28B	109.5
C3—C2—H2	123.1	H28A—C28—H28B	109.5
C4—C3—C2	111.7 (5)	N7—C28—H28C	109.5
C4—C3—H3B	124.1	H28A—C28—H28C	109.5
C2—C3—H3B	124.1	H28B—C28—H28C	109.5
C3—C4—C5	129.6 (5)	N7—C29—H29A	109.5
C3—C4—S1	110.8 (4)	N7—C29—H29B	109.5
C5—C4—S1	119.6 (4)	H29A—C29—H29B	109.5
O1—C5—N1	124.8 (5)	N7—C29—H29C	109.5
O1—C5—C4	120.5 (4)	H29A—C29—H29C	109.5
N1—C5—C4	114.7 (5)	H29B—C29—H29C	109.5
O2—C6—N3	129.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1w1···O2	0.84 (1)	2.06 (3)	2.859 (5)	158 (6)
O1W—H1w2···O5	0.84 (1)	2.31 (8)	2.771 (9)	115 (7)
N3—H3N···O1Wⁱ	0.84 (1)	1.98 (1)	2.813 (6)	173 (5)
N6—H6N···O4ⁱⁱ	0.84 (1)	2.06 (2)	2.884 (5)	169 (5)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₃H₈N₃O₂S)₂]·C₃H₇NO·H₂O
M_r	697.05
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	11.5250 (8), 12.0656 (8), 13.4643 (9)
α, β, γ (°)	105.913 (1), 100.531 (1), 114.754 (1)
V (Å³)	1537.25 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.22 × 0.16 × 0.08

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.812, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	13275, 6630, 3036
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.182, 0.98
No. of reflections	6630
No. of parameters	432
No. of restraints	77
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.35

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Zn1—O1	2.103 (3)	Zn1—O4	2.440 (3)
Zn1—O2	2.370 (3)	Zn1—N2	2.017 (4)
Zn1—O3	2.043 (3)	Zn1—N5	2.022 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1w1···O2	0.84 (1)	2.06 (3)	2.859 (5)	158 (6)
O1W—H1w2···O5	0.84 (1)	2.31 (8)	2.771 (9)	115 (7)
N3—H3N···O1Wⁱ	0.84 (1)	1.98 (1)	2.813 (6)	173 (5)
N6—H6N···O4ⁱⁱ	0.84 (1)	2.06 (2)	2.884 (5)	169 (5)

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

Acknowledgements

The authors thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rodríguez-Argüelles, M. C., Cao, R., García-Deibe, A. M., Pelizzi, C., Sanmartín-Matalobos, J. & Zani, F. (2009). Polyhedron, 28, 2187–2195. 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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