[(E)-But-2-enoato-κO]chlorido(2,2′-diamino-4,4′-bi-1,3-thia­zole-κ2N3,N3′)zinc(II) monohydrate

Du, M.; Wang, Y.-L.; Liu, B.-X.; Xu, D.-J.

doi:10.1107/S160053681001113X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m466

doi:10.1107/S160053681001113X

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[(E)-But-2-enoato-κO]chlorido(2,2′-diamino-4,4′-bi-1,3-thiazole-κ²N³,N^3′)zinc(II) monohydrate

Mei Du,^a Yan-Li Wang,^a Bing-Xin Liu ^a and Duan-Jun Xu ^b ^*

^aDepartment of Chemistry, Shanghai University, People's Republic of China, and ^bDepartment of Chemistry, Zhejiang University, People's Republic of China
^*Correspondence e-mail: xudj@mail.hz.zj.cn

(Received 23 March 2010; accepted 24 March 2010; online 27 March 2010)

In the title compound, [Zn(C₄H₅O₂)Cl(C₆H₆N₄S₂)]·H₂O, the Zn^II cation is coordinated by a bidentate diaminobithiazole (DABT) ligand, a but-2-enoate anion and a Cl⁻ anion in a distorted tetrahedral geometry. Within the DABT ligand, the two thiazole rings are twisted to each other at a dihedral angle of 4.38 (10)°. An intramolecular N—H⋯O interaction occurs. The centroid–centroid distance of 3.6650 (17) Å and partially overlapped arrangement between nearly parallel thiazole rings of adjacent complexes indicate the existence of π–π stacking in the crystal structure. Extensive O—H⋯Cl, O—H⋯O, N—H⋯Cl and N—H⋯O hydrogen bonding helps to stabilize the crystal structure.

Related literature

For the potential applications of metal complexes of diaminobithiazole in the biological field, see: Waring (1981 ); Fisher et al. (1985 ). For dihedral angles between thiazole rings in diaminobithiazole complexes, see: Du et al. (2010 ); Zhang et al. (2006 ).

Experimental

Crystal data

[Zn(C₄H₅O₂)Cl(C₆H₆N₄S₂)]·H₂O
M_r = 402.18
Monoclinic, P 2₁ /n
a = 7.2782 (13) Å
b = 16.2846 (16) Å
c = 13.237 (2) Å
β = 99.252 (16)°
V = 1548.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.04 mm⁻¹
T = 294 K
0.36 × 0.30 × 0.24 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.75, T_max = 0.88
7862 measured reflections
2735 independent reflections
2293 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.080
S = 1.05
2735 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn—O1	1.961 (2)
Zn—N1	2.029 (2)
Zn—N3	2.060 (2)
Zn—Cl1	2.2223 (9)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯Cl1ⁱ	0.86	2.56	3.345 (3)	152
O1W—H1B⋯O1	0.86	2.04	2.859 (4)	160
N2—H2A⋯O2	0.86	2.22	2.959 (4)	144
N2—H2B⋯O1Wⁱⁱ	0.86	2.23	3.032 (4)	154
N4—H4A⋯O1W	0.86	2.30	3.043 (4)	145
N4—H4B⋯Cl1ⁱⁱⁱ	0.86	2.66	3.393 (3)	144
Symmetry codes: (i) x-1, y, z; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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/S160053681001113X/ng2750sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681001113X/ng2750Isup2.hkl

checkCIF report

Comment top

Some metal complexes with 2,2'-diamino-4,4'-bi-1,3-thiazole (DABT) have shown the potential application in the biological field (Waring, 1981; Fisher et al., 1985). As a part of serial structural investigation of metal complexes with DABT, the title Zn^II complex was prepared in the laboratory and its X-ray structure is presented here.

The molecular structure of the title compound is shown in Fig. 1. The Zn^II cation is coordinated by a diaminobithiazole (DABT) ligand, a but-2-enoate anion and a Cl^- anion in a distorted tetrahedral geometry (Table 1). Within the DABT ligand the two thiazole rings are twisted to each other at a dihedral angle of 4.38 (10)°, which agrees with 9.51 (17)° found in a Pb^II complex of DABT (Du et al., 2010) and 9.5 (2)° found in a Cd^II complex of DABT (Zhang et al., 2006). The partially overlapped arrangement of centroids distance of 3.6650 (17) Å between nearly parallel thiazole rings of the adjacent complexes indicate the existence of π-π stacking in the crystal structure (Fig. 2). The extensive hydrogen bonding help to stabilize the crystal structure (Table 2).

Related literature top

For the potential applications of metal complexes of diaminobithiazole in the biological field, see: Waring (1981); Fisher et al. (1985). For dihedral angles between thiazole rings in diaminobithiazole complexes, see: Du et al. (2010); Zhang et al. (2006).

Experimental top

A water-ethanol solution (20 ml, 1:1) of DABT (0.10 g, 0.5 mmol) and ZnCl₂ (0.07 g, 0.5 mmol) was refluxed for 10 min, then an aqueous solution (20 ml) of (E)-but-2-enoatic acid (0.09 g, 1 mmol) and NaOH (0.04 g, 1 mmol) was mixed with the above solution. The mixture was refluxed for 6 h and then filtered. The single crystals of the title compound were obtained from the filtrate after a week.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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 the title compound with 40% probability displacement ellipsoids. Dashed lines indicate the hydrogen bonding.
	Fig. 2. The partially overlapped arrangement between thiazole rings showing π-π stacking [symmetry code: (i) 1-x, -y, 1-z].

[(E)-But-2-enoato-κO]chlorido(2,2'-diamino-4,4'-bi-1,3- thiazole-κ²N³,N^3')zinc(II) monohydrate top

Crystal data top

[Zn(C₄H₅O₂)Cl(C₆H₆N₄S₂)]·H₂O	F(000) = 816
M_r = 402.18	D_x = 1.725 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3446 reflections
a = 7.2782 (13) Å	θ = 2.0–24.6°
b = 16.2846 (16) Å	µ = 2.04 mm⁻¹
c = 13.237 (2) Å	T = 294 K
β = 99.252 (16)°	Block, yellow
V = 1548.5 (4) Å³	0.36 × 0.30 × 0.24 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2735 independent reflections
Radiation source: fine-focus sealed tube	2293 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
T_min = 0.75, T_max = 0.88	k = −12→19
7862 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0353P)² + 1.093P] where P = (F_o² + 2F_c²)/3
2735 reflections	(Δ/σ)_max = 0.002
191 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Zn(C₄H₅O₂)Cl(C₆H₆N₄S₂)]·H₂O	V = 1548.5 (4) Å³
M_r = 402.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.2782 (13) Å	µ = 2.04 mm⁻¹
b = 16.2846 (16) Å	T = 294 K
c = 13.237 (2) Å	0.36 × 0.30 × 0.24 mm
β = 99.252 (16)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2735 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2293 reflections with I > 2σ(I)
T_min = 0.75, T_max = 0.88	R_int = 0.026
7862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.05	Δρ_max = 0.71 e Å⁻³
2735 reflections	Δρ_min = −0.45 e Å⁻³
191 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	0.77894 (5)	0.12724 (2)	0.64617 (2)	0.03260 (13)
Cl1	1.01129 (13)	0.21725 (6)	0.67179 (7)	0.0541 (3)
S1	0.93933 (12)	−0.14538 (5)	0.65212 (7)	0.0433 (2)
S2	0.56191 (12)	0.09881 (5)	0.30033 (6)	0.0418 (2)
N1	0.8456 (3)	0.00649 (15)	0.64140 (17)	0.0314 (6)
N2	0.9835 (4)	−0.03495 (18)	0.8057 (2)	0.0483 (7)
H2A	0.9737	0.0134	0.8305	0.058*
H2B	1.0326	−0.0740	0.8447	0.058*
N3	0.6716 (3)	0.10813 (15)	0.49432 (17)	0.0299 (5)
N4	0.5365 (4)	0.22969 (16)	0.4215 (2)	0.0444 (7)
H4A	0.5508	0.2545	0.4796	0.053*
H4B	0.4859	0.2549	0.3670	0.053*
O1	0.5737 (3)	0.15367 (14)	0.72007 (17)	0.0471 (6)
O2	0.7729 (4)	0.11162 (17)	0.8535 (2)	0.0630 (7)
O1W	0.4071 (4)	0.29467 (17)	0.6138 (2)	0.0726 (8)
H1A	0.2909	0.2835	0.6079	0.087*
H1B	0.4522	0.2592	0.6587	0.087*
C1	0.9224 (4)	−0.04933 (19)	0.7066 (2)	0.0351 (7)
C2	0.8373 (4)	−0.10659 (19)	0.5354 (2)	0.0396 (8)
H2	0.8137	−0.1368	0.4751	0.047*
C3	0.7965 (4)	−0.02684 (18)	0.5437 (2)	0.0316 (7)
C4	0.7091 (4)	0.02855 (18)	0.4637 (2)	0.0309 (7)
C5	0.6607 (4)	0.0136 (2)	0.3637 (2)	0.0386 (7)
H5	0.6782	−0.0363	0.3325	0.046*
C6	0.5924 (4)	0.15275 (19)	0.4159 (2)	0.0333 (7)
C7	0.6148 (5)	0.1325 (2)	0.8138 (3)	0.0448 (8)
C8	0.4511 (6)	0.1316 (2)	0.8698 (3)	0.0541 (9)
H8	0.3377	0.1509	0.8357	0.065*
C9	0.4583 (6)	0.1061 (2)	0.9613 (3)	0.0623 (11)
H9	0.5745	0.0909	0.9963	0.075*
C10	0.2972 (7)	0.0984 (3)	1.0172 (3)	0.0724 (13)
H10A	0.3061	0.1397	1.0696	0.109*
H10B	0.2981	0.0450	1.0479	0.109*
H10C	0.1834	0.1057	0.9702	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.0384 (2)	0.0298 (2)	0.0298 (2)	−0.00060 (15)	0.00584 (14)	−0.00417 (15)
Cl1	0.0597 (6)	0.0545 (6)	0.0507 (5)	−0.0236 (4)	0.0161 (4)	−0.0186 (4)
S1	0.0460 (5)	0.0295 (4)	0.0551 (5)	0.0035 (4)	0.0103 (4)	0.0042 (4)
S2	0.0460 (5)	0.0489 (5)	0.0286 (4)	−0.0057 (4)	0.0004 (3)	−0.0015 (4)
N1	0.0353 (14)	0.0292 (13)	0.0305 (13)	−0.0011 (11)	0.0076 (10)	0.0008 (11)
N2	0.0629 (19)	0.0439 (17)	0.0357 (15)	0.0110 (14)	0.0010 (13)	0.0064 (13)
N3	0.0316 (13)	0.0310 (13)	0.0279 (12)	−0.0041 (11)	0.0069 (10)	−0.0008 (10)
N4	0.0572 (18)	0.0363 (16)	0.0371 (15)	0.0029 (13)	0.0001 (13)	0.0059 (12)
O1	0.0528 (15)	0.0469 (14)	0.0449 (14)	0.0028 (11)	0.0173 (11)	−0.0083 (11)
O2	0.0653 (19)	0.0609 (17)	0.0627 (17)	0.0061 (14)	0.0103 (14)	−0.0015 (14)
O1W	0.0642 (18)	0.072 (2)	0.084 (2)	−0.0139 (15)	0.0188 (15)	−0.0228 (16)
C1	0.0323 (17)	0.0348 (17)	0.0397 (18)	−0.0008 (14)	0.0100 (13)	0.0035 (14)
C2	0.046 (2)	0.0319 (18)	0.0428 (18)	−0.0028 (14)	0.0115 (15)	−0.0064 (14)
C3	0.0298 (16)	0.0315 (17)	0.0353 (16)	−0.0052 (13)	0.0110 (12)	−0.0043 (13)
C4	0.0310 (16)	0.0304 (16)	0.0329 (16)	−0.0055 (13)	0.0098 (12)	−0.0025 (13)
C5	0.0449 (19)	0.0372 (18)	0.0343 (17)	−0.0060 (15)	0.0081 (14)	−0.0069 (14)
C6	0.0337 (17)	0.0347 (17)	0.0309 (16)	−0.0053 (13)	0.0038 (13)	0.0006 (13)
C7	0.056 (2)	0.0315 (18)	0.050 (2)	−0.0028 (16)	0.0166 (17)	−0.0093 (16)
C8	0.062 (2)	0.051 (2)	0.051 (2)	0.0083 (18)	0.0151 (18)	−0.0034 (18)
C9	0.079 (3)	0.050 (2)	0.062 (3)	0.014 (2)	0.022 (2)	0.002 (2)
C10	0.097 (3)	0.063 (3)	0.069 (3)	0.017 (2)	0.048 (3)	0.011 (2)

Geometric parameters (Å, º) top

Zn—O1	1.961 (2)	O1—C7	1.275 (4)
Zn—N1	2.029 (2)	O2—C7	1.234 (4)
Zn—N3	2.060 (2)	O1W—H1A	0.8564
Zn—Cl1	2.2223 (9)	O1W—H1B	0.8550
S1—C2	1.723 (3)	C2—C3	1.340 (4)
S1—C1	1.735 (3)	C2—H2	0.9300
S2—C5	1.718 (3)	C3—C4	1.457 (4)
S2—C6	1.747 (3)	C4—C5	1.336 (4)
N1—C1	1.315 (4)	C5—H5	0.9300
N1—C3	1.395 (4)	C7—C8	1.502 (5)
N2—C1	1.336 (4)	C8—C9	1.273 (5)
N2—H2A	0.8600	C8—H8	0.9300
N2—H2B	0.8600	C9—C10	1.490 (5)
N3—C6	1.321 (4)	C9—H9	0.9300
N3—C4	1.398 (4)	C10—H10A	0.9600
N4—C6	1.323 (4)	C10—H10B	0.9600
N4—H4A	0.8600	C10—H10C	0.9600
N4—H4B	0.8600

O1—Zn—N1	115.69 (10)	C2—C3—N1	115.2 (3)
O1—Zn—N3	108.68 (10)	C2—C3—C4	128.1 (3)
N1—Zn—N3	83.01 (9)	N1—C3—C4	116.7 (2)
O1—Zn—Cl1	113.65 (7)	C5—C4—N3	115.0 (3)
N1—Zn—Cl1	117.66 (7)	C5—C4—C3	128.5 (3)
N3—Zn—Cl1	114.11 (7)	N3—C4—C3	116.5 (2)
C2—S1—C1	89.60 (15)	C4—C5—S2	111.1 (2)
C5—S2—C6	89.66 (15)	C4—C5—H5	124.5
C1—N1—C3	111.0 (2)	S2—C5—H5	124.5
C1—N1—Zn	136.7 (2)	N3—C6—N4	125.2 (3)
C3—N1—Zn	112.28 (18)	N3—C6—S2	112.9 (2)
C1—N2—H2A	120.0	N4—C6—S2	121.9 (2)
C1—N2—H2B	120.0	O2—C7—O1	123.1 (3)
H2A—N2—H2B	120.0	O2—C7—C8	123.1 (3)
C6—N3—C4	111.3 (2)	O1—C7—C8	113.7 (3)
C6—N3—Zn	137.1 (2)	C9—C8—C7	124.0 (4)
C4—N3—Zn	111.23 (18)	C9—C8—H8	118.0
C6—N4—H4A	120.0	C7—C8—H8	118.0
C6—N4—H4B	120.0	C8—C9—C10	125.8 (4)
H4A—N4—H4B	120.0	C8—C9—H9	117.1
C7—O1—Zn	110.3 (2)	C10—C9—H9	117.1
H1A—O1W—H1B	100.6	C9—C10—H10A	109.5
N1—C1—N2	124.2 (3)	C9—C10—H10B	109.5
N1—C1—S1	113.6 (2)	H10A—C10—H10B	109.5
N2—C1—S1	122.1 (2)	C9—C10—H10C	109.5
C3—C2—S1	110.6 (2)	H10A—C10—H10C	109.5
C3—C2—H2	124.7	H10B—C10—H10C	109.5
S1—C2—H2	124.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···Cl1ⁱ	0.86	2.56	3.345 (3)	152
O1W—H1B···O1	0.86	2.04	2.859 (4)	160
N2—H2A···O2	0.86	2.22	2.959 (4)	144
N2—H2B···O1Wⁱⁱ	0.86	2.23	3.032 (4)	154
N4—H4A···O1W	0.86	2.30	3.043 (4)	145
N4—H4B···Cl1ⁱⁱⁱ	0.86	2.66	3.393 (3)	144

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

Experimental details

Crystal data
Chemical formula	[Zn(C₄H₅O₂)Cl(C₆H₆N₄S₂)]·H₂O
M_r	402.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	7.2782 (13), 16.2846 (16), 13.237 (2)
β (°)	99.252 (16)
V (Å³)	1548.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.04
Crystal size (mm)	0.36 × 0.30 × 0.24

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.75, 0.88
No. of measured, independent and observed [I > 2σ(I)] reflections	7862, 2735, 2293
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.080, 1.05
No. of reflections	2735
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.45

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Zn—O1	1.961 (2)	Zn—N3	2.060 (2)
Zn—N1	2.029 (2)	Zn—Cl1	2.2223 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···Cl1ⁱ	0.86	2.56	3.345 (3)	152
O1W—H1B···O1	0.86	2.04	2.859 (4)	160
N2—H2A···O2	0.86	2.22	2.959 (4)	144
N2—H2B···O1Wⁱⁱ	0.86	2.23	3.032 (4)	154
N4—H4A···O1W	0.86	2.30	3.043 (4)	145
N4—H4B···Cl1ⁱⁱⁱ	0.86	2.66	3.393 (3)	144

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

Acknowledgements

The project was supported by the ZIJIN project of Zhejiang University, China.

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