Poly[bis­(N,N-dimethyl­acetamide)-1κO,2κO-bis­(μ4-thio­phene-2,5-di­car­boxyl­ato-1:2:1′:2′κ4O2:O2′:O5:O5′)dizinc]

Du, M.-M.; Ng, S.W.

doi:10.1107/S160053681103981X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1488

doi:10.1107/S160053681103981X

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Poly[bis(N,N-dimethylacetamide)-1κO,2κO-bis(μ₄-thiophene-2,5-dicarboxylato-1:2:1′:2′κ⁴O²:O^2′:O⁵:O^5′)dizinc]

Ming-Ming Du ^a and Seik Weng Ng ^b,^c ^*

^aYankuang Guohong Chemical Co. Ltd, Zoucheng 273500, 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 26 September 2011; accepted 28 September 2011; online 5 October 2011)

In the title polymeric complex, [Zn₂(C₆H₂O₄S)₂(C₄H₉NO)₂]_n, each carboxylate group of the thiophene-2,5-dicarboxylate dianion bridges a pair of inversion-related dimethylacetamide-coordinated Zn^II atoms, generating a layer motif parallel to (101). The Zn^II atom shows a distorted square-pyramidal coordination; the apical site is occupied by the O atom of the dimethylacetamide molecule, whereas the four basal sites are occupied by carboxylate O atoms. In the crystal, the dimethylacetamide molecule is disordered over two positions in a 0.72 (1):0.28 (1) ratio in respect of the C atoms.

Related literature

For the 1,10-phenanthroline adduct of zinc 2,5-thiophenedicarboxylate, see: Chen et al. (1999 ). For bond-length dimensions of the 2,5-thiophenedicarboxylate ion, see: Wu et al. (2006 ).

Experimental

Crystal data

[Zn₂(C₆H₂O₄S)₂(C₄H₉NO)₂]
M_r = 645.26
Monoclinic, P 2₁ /n
a = 8.4866 (2) Å
b = 14.8476 (4) Å
c = 10.1406 (3) Å
β = 100.734 (2)°
V = 1255.41 (6) Å³
Z = 2
Mo Kα radiation
μ = 2.13 mm⁻¹
T = 153 K
0.20 × 0.20 × 0.10 mm

Data collection

Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.675, T_max = 0.815
7660 measured reflections
2841 independent reflections
1990 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.089
S = 0.93
2841 reflections
182 parameters
5 restraints
H-atom parameters constrained
Δρ_max = 1.13 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S160053681103981X/xu5337sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681103981X/xu5337Isup2.hkl

checkCIF report

Comment top

The dianions of rigid aromatic carboxylic acids such as phthalic, isophthalic and terephathalic acids furnish coordination polymers with divalent metal ions. The 2,5-thiophenedicarboxylate anion is less well studied; the only crystal structure study of a zinc(II) system is that of the zinc 2,5-thiophenedicarboxylate adduct with 1,10-phenanthroline (Chen et al., 1999). In this study, the dimethylacetamide (DMA) used as solvent in the synthesis is incorporate into the crystal structure. Polymeric [Zn₂(C₄H₉NO)₂(C₆H₂O₄S)₂]_n (Scheme I) has the –CO₂ parts of the thiophene-2,5-dicarboxylate dianion each bridging a pair of inversion-related, dimethylacetamide-coordinated zinc^II atoms to generate a layer motif (Fig. 1). The Zn^II atom shows square-pyramidal coordination; the apical site is occupied by the O atom of the DMA molecule. Bond dimensions involving the carboxylate unit are similar to those reported for ethylenediammonium thiophene-2,5-dicarboxylate dihydrate (Wu et al., 2006).

Related literature top

For the 1,10-phenanthroline adduct of zinc 2,5-thiophenedicarboxylate, see: Chen et al. (1999). For bond dimensions of the 2,5-thiophenedicarboxylate ion, see: Wu et al. (2006).

Experimental top

2,5-Thiophenedicarboxylic acid (0.09 g, 0.5 mmol) and zinc nitrate hexahydrate (0.30 g,0.5 mmol) were dissolved in dimethylacetamide (10 ml). The solution was placed in a 25-ml flask, heated at 90 °C for 5 days. Colorless cystals separated from the solution upon cooling it to room temperature.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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. Thermal ellipsoid plot (Barbour, 2001) of a portion of polymeric Zn₂(C₄H₉NO)₂(C₆H₂O₄S)₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the dimethylacetamide unit is not shown. Only the asymmetric unit is labeled.

Poly[bis(N,N-dimethylacetamide)-1κO,2κO- bis(µ₄-thiophene-2,5-dicarboxylato- 1:2:1':2'κ⁴O²:O^2':O⁵:O^5')dizinc] top

Crystal data top

[Zn₂(C₆H₂O₄S)₂(C₄H₉NO)₂]	F(000) = 656
M_r = 645.26	D_x = 1.707 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3158 reflections
a = 8.4866 (2) Å	θ = 2.4–29.7°
b = 14.8476 (4) Å	µ = 2.13 mm⁻¹
c = 10.1406 (3) Å	T = 153 K
β = 100.734 (2)°	Block, colorless
V = 1255.41 (6) Å³	0.20 × 0.20 × 0.10 mm
Z = 2

Data collection top

Gemini S Ultra diffractometer	2841 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1990 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 16.1903 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −10→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −19→17
T_min = 0.675, T_max = 0.815	l = −13→13
7660 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0535P)²] where P = (F_o² + 2F_c²)/3
2841 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 1.13 e Å⁻³
5 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Zn₂(C₆H₂O₄S)₂(C₄H₉NO)₂]	V = 1255.41 (6) Å³
M_r = 645.26	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4866 (2) Å	µ = 2.13 mm⁻¹
b = 14.8476 (4) Å	T = 153 K
c = 10.1406 (3) Å	0.20 × 0.20 × 0.10 mm
β = 100.734 (2)°

Data collection top

Gemini S Ultra diffractometer	2841 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1990 reflections with I > 2σ(I)
T_min = 0.675, T_max = 0.815	R_int = 0.029
7660 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	5 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 0.93	Δρ_max = 1.13 e Å⁻³
2841 reflections	Δρ_min = −0.55 e Å⁻³
182 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.64210 (4)	0.53115 (2)	0.60386 (3)	0.02026 (12)
S1	0.70730 (9)	0.23894 (5)	0.23932 (7)	0.02835 (19)
O1	0.7270 (3)	0.42738 (18)	0.5087 (2)	0.0482 (7)
O2	0.5233 (3)	0.38003 (16)	0.3549 (2)	0.0392 (6)
O3	1.0411 (4)	0.06503 (19)	0.2061 (2)	0.0544 (8)
O4	0.8306 (3)	0.10976 (17)	0.0555 (2)	0.0432 (6)
O5	0.8383 (3)	0.55742 (18)	0.7354 (2)	0.0428 (6)
N1	1.0425 (3)	0.5890 (2)	0.8985 (3)	0.0387 (7)
C1	0.6643 (4)	0.3774 (2)	0.4147 (3)	0.0262 (7)
C2	0.7708 (4)	0.3090 (2)	0.3709 (3)	0.0284 (7)
C3	0.9309 (5)	0.2970 (3)	0.4216 (4)	0.0507 (10)
H3	0.9908	0.3328	0.4909	0.061*
C4	0.9958 (5)	0.2253 (3)	0.3589 (4)	0.0550 (12)
H4	1.1043	0.2064	0.3830	0.066*
C5	0.8871 (4)	0.1853 (2)	0.2597 (3)	0.0312 (7)
C6	0.9207 (4)	0.1141 (2)	0.1669 (3)	0.0299 (7)
C7	0.8881 (5)	0.6019 (3)	0.8283 (4)	0.0298 (11)	0.72 (1)
C8	0.7793 (6)	0.6729 (4)	0.8697 (5)	0.0425 (13)	0.72 (1)
H8A	0.6843	0.6800	0.7990	0.064*	0.72 (1)
H8B	0.8368	0.7303	0.8839	0.064*	0.72 (1)
H8C	0.7461	0.6544	0.9532	0.064*	0.72 (1)
C9	1.0963 (7)	0.6473 (4)	1.0207 (5)	0.0471 (14)	0.72 (1)
H9A	1.1523	0.7004	0.9953	0.071*	0.72 (1)
H9B	1.1691	0.6128	1.0887	0.071*	0.72 (1)
H9C	1.0027	0.6663	1.0573	0.071*	0.72 (1)
C10	1.1457 (6)	0.5301 (4)	0.8593 (6)	0.0488 (14)	0.72 (1)
H10A	1.2457	0.5612	0.8526	0.073*	0.72 (1)
H10B	1.0980	0.5049	0.7716	0.073*	0.72 (1)
H10C	1.1683	0.4813	0.9253	0.073*	0.72 (1)
C7'	0.9677 (10)	0.5478 (7)	0.7833 (9)	0.0298 (11)	0.28
C8'	1.0369 (16)	0.4825 (8)	0.6974 (13)	0.0425 (13)	0.28
H8'1	0.9955	0.4220	0.7093	0.064*	0.279 (6)
H8'2	1.1541	0.4823	0.7234	0.064*	0.279 (6)
H8'3	1.0065	0.5004	0.6030	0.064*	0.279 (6)
C9'	1.2159 (12)	0.5540 (10)	0.9429 (15)	0.0471 (14)	0.28
H9'1	1.2414	0.5502	1.0411	0.071*	0.279 (6)
H9'2	1.2907	0.5955	0.9114	0.071*	0.279 (6)
H9'3	1.2254	0.4941	0.9044	0.071*	0.279 (6)
C10'	0.9967 (18)	0.6518 (8)	0.9728 (14)	0.0488 (14)	0.28
H10D	1.0135	0.6314	1.0663	0.073*	0.279 (6)
H10E	0.8827	0.6648	0.9412	0.073*	0.279 (6)
H10F	1.0597	0.7066	0.9669	0.073*	0.279 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02204 (18)	0.01473 (18)	0.02585 (19)	−0.00035 (14)	0.00927 (13)	0.00035 (14)
S1	0.0292 (4)	0.0271 (4)	0.0297 (4)	0.0037 (3)	0.0078 (3)	−0.0091 (3)
O1	0.0437 (16)	0.0457 (16)	0.0504 (15)	0.0201 (12)	−0.0037 (12)	−0.0284 (13)
O2	0.0275 (13)	0.0387 (14)	0.0508 (14)	0.0083 (10)	0.0055 (10)	−0.0228 (12)
O3	0.071 (2)	0.0465 (16)	0.0451 (15)	0.0326 (15)	0.0095 (13)	−0.0162 (13)
O4	0.0420 (15)	0.0471 (16)	0.0420 (14)	0.0071 (12)	0.0123 (11)	−0.0218 (12)
O5	0.0324 (14)	0.0489 (16)	0.0444 (14)	−0.0157 (12)	−0.0001 (11)	0.0031 (13)
N1	0.0342 (17)	0.0409 (18)	0.0382 (16)	−0.0090 (14)	−0.0002 (13)	0.0064 (14)
C1	0.0343 (18)	0.0199 (16)	0.0261 (16)	0.0037 (13)	0.0102 (13)	0.0001 (13)
C2	0.0320 (18)	0.0264 (17)	0.0258 (15)	0.0058 (13)	0.0030 (13)	−0.0080 (13)
C3	0.052 (3)	0.052 (2)	0.043 (2)	0.018 (2)	−0.0052 (17)	−0.0188 (19)
C4	0.043 (2)	0.059 (3)	0.056 (2)	0.025 (2)	−0.0071 (19)	−0.021 (2)
C5	0.0386 (19)	0.0244 (17)	0.0318 (16)	0.0068 (14)	0.0094 (13)	−0.0052 (14)
C6	0.0369 (19)	0.0190 (17)	0.0393 (19)	0.0001 (14)	0.0215 (15)	−0.0049 (14)
C7	0.031 (2)	0.025 (2)	0.036 (2)	−0.0063 (17)	0.0121 (18)	0.0012 (18)
C8	0.036 (3)	0.044 (3)	0.047 (3)	0.003 (2)	0.007 (2)	−0.016 (2)
C9	0.040 (3)	0.057 (4)	0.042 (3)	−0.010 (2)	0.002 (2)	0.006 (2)
C10	0.036 (3)	0.052 (3)	0.059 (3)	−0.003 (2)	0.010 (2)	0.012 (3)
C7'	0.031 (2)	0.025 (2)	0.036 (2)	−0.0063 (17)	0.0121 (18)	0.0012 (18)
C8'	0.036 (3)	0.044 (3)	0.047 (3)	0.003 (2)	0.007 (2)	−0.016 (2)
C9'	0.040 (3)	0.057 (4)	0.042 (3)	−0.010 (2)	0.002 (2)	0.006 (2)
C10'	0.036 (3)	0.052 (3)	0.059 (3)	−0.003 (2)	0.010 (2)	0.012 (3)

Geometric parameters (Å, º) top

Zn1—O5	1.969 (2)	C3—C4	1.404 (5)
Zn1—O1	2.021 (2)	C3—H3	0.9500
Zn1—O2ⁱ	2.026 (2)	C4—C5	1.367 (5)
Zn1—O4ⁱⁱ	2.041 (2)	C4—H4	0.9500
Zn1—O3ⁱⁱⁱ	2.044 (2)	C5—C6	1.479 (4)
Zn1—Zn1ⁱ	3.0360 (6)	C7—C8	1.511 (6)
S1—C2	1.699 (3)	C8—H8A	0.9800
S1—C5	1.699 (3)	C8—H8B	0.9800
O1—C1	1.246 (4)	C8—H8C	0.9800
O2—C1	1.237 (4)	C9—H9A	0.9800
O2—Zn1ⁱ	2.026 (2)	C9—H9B	0.9800
O3—C6	1.257 (4)	C9—H9C	0.9800
O3—Zn1^iv	2.044 (2)	C10—H10A	0.9800
O4—C6	1.242 (4)	C10—H10B	0.9800
O4—Zn1^v	2.041 (2)	C10—H10C	0.9800
O5—C7'	1.125 (8)	C7'—C8'	1.495 (10)
O5—C7	1.164 (4)	C8'—H8'1	0.9800
N1—C10'	1.303 (10)	C8'—H8'2	0.9800
N1—C10	1.349 (6)	C8'—H8'3	0.9800
N1—C7'	1.366 (8)	C9'—H9'1	0.9800
N1—C7	1.383 (5)	C9'—H9'2	0.9800
N1—C9	1.510 (5)	C9'—H9'3	0.9800
N1—C9'	1.547 (9)	C10'—H10D	0.9800
C1—C2	1.481 (4)	C10'—H10E	0.9800
C2—C3	1.372 (5)	C10'—H10F	0.9800

O5—Zn1—O1	98.22 (11)	C4—C3—H3	124.0
O5—Zn1—O2ⁱ	105.20 (10)	C5—C4—C3	113.3 (3)
O1—Zn1—O2ⁱ	156.55 (10)	C5—C4—H4	123.4
O5—Zn1—O4ⁱⁱ	102.52 (10)	C3—C4—H4	123.4
O1—Zn1—O4ⁱⁱ	87.40 (12)	C4—C5—C6	126.5 (3)
O2ⁱ—Zn1—O4ⁱⁱ	88.65 (11)	C4—C5—S1	110.7 (2)
O5—Zn1—O3ⁱⁱⁱ	100.14 (10)	C6—C5—S1	122.2 (2)
O1—Zn1—O3ⁱⁱⁱ	85.99 (13)	O4—C6—O3	125.8 (3)
O2ⁱ—Zn1—O3ⁱⁱⁱ	88.75 (12)	O4—C6—C5	117.2 (3)
O4ⁱⁱ—Zn1—O3ⁱⁱⁱ	157.07 (10)	O3—C6—C5	117.0 (3)
O5—Zn1—Zn1ⁱ	173.08 (8)	O5—C7—N1	120.3 (4)
O1—Zn1—Zn1ⁱ	75.18 (7)	O5—C7—C8	118.2 (4)
O2ⁱ—Zn1—Zn1ⁱ	81.37 (6)	N1—C7—C8	121.5 (4)
O4ⁱⁱ—Zn1—Zn1ⁱ	79.50 (7)	N1—C9—H9A	109.5
O3ⁱⁱⁱ—Zn1—Zn1ⁱ	77.59 (7)	N1—C9—H9B	109.5
C2—S1—C5	92.59 (15)	N1—C9—H9C	109.5
C1—O1—Zn1	132.8 (2)	N1—C10—H10A	109.5
C1—O2—Zn1ⁱ	124.3 (2)	N1—C10—H10B	109.5
C6—O3—Zn1^iv	129.6 (2)	N1—C10—H10C	109.5
C6—O4—Zn1^v	127.4 (2)	O5—C7'—N1	125.0 (7)
C7'—O5—C7	62.9 (5)	O5—C7'—C8'	106.8 (7)
C7'—O5—Zn1	154.4 (5)	N1—C7'—C8'	128.2 (8)
C7—O5—Zn1	142.7 (3)	C7'—C8'—H8'1	109.5
C10'—N1—C10	156.1 (8)	C7'—C8'—H8'2	109.5
C10'—N1—C7'	132.4 (8)	H8'1—C8'—H8'2	109.5
C10—N1—C7'	71.4 (5)	C7'—C8'—H8'3	109.5
C10'—N1—C7	81.0 (7)	H8'1—C8'—H8'3	109.5
C10—N1—C7	122.9 (4)	H8'2—C8'—H8'3	109.5
C10—N1—C9	119.9 (4)	N1—C9'—H9'1	109.5
C7—N1—C9	117.1 (4)	N1—C9'—H9'2	109.5
C10'—N1—C9'	116.2 (9)	H9'1—C9'—H9'2	109.5
C7'—N1—C9'	111.3 (7)	N1—C9'—H9'3	109.5
O2—C1—O1	126.3 (3)	H9'1—C9'—H9'3	109.5
O2—C1—C2	117.6 (3)	H9'2—C9'—H9'3	109.5
O1—C1—C2	116.1 (3)	N1—C10'—H10D	109.5
C3—C2—C1	126.5 (3)	N1—C10'—H10E	109.5
C3—C2—S1	111.2 (2)	H10D—C10'—H10E	109.5
C1—C2—S1	122.2 (2)	N1—C10'—H10F	109.5
C2—C3—C4	111.9 (3)	H10D—C10'—H10F	109.5
C2—C3—H3	124.0	H10E—C10'—H10F	109.5

O5—Zn1—O1—C1	178.6 (3)	C4—C5—C6—O4	−152.9 (4)
O2ⁱ—Zn1—O1—C1	1.5 (5)	S1—C5—C6—O4	17.8 (4)
O4ⁱⁱ—Zn1—O1—C1	−79.1 (3)	C4—C5—C6—O3	24.9 (5)
O3ⁱⁱⁱ—Zn1—O1—C1	78.9 (3)	S1—C5—C6—O3	−164.4 (3)
O1—Zn1—O5—C7'	2.8 (14)	C7'—O5—C7—N1	−5.0 (7)
O2ⁱ—Zn1—O5—C7'	−178.3 (14)	Zn1—O5—C7—N1	173.8 (3)
O4ⁱⁱ—Zn1—O5—C7'	−86.3 (14)	C7'—O5—C7—C8	175.6 (8)
O3ⁱⁱⁱ—Zn1—O5—C7'	90.2 (14)	Zn1—O5—C7—C8	−5.7 (7)
O1—Zn1—O5—C7	−174.5 (4)	C10'—N1—C7—O5	−176.9 (7)
O2ⁱ—Zn1—O5—C7	4.3 (5)	C10—N1—C7—O5	4.7 (6)
O4ⁱⁱ—Zn1—O5—C7	96.3 (4)	C7'—N1—C7—O5	4.7 (6)
O3ⁱⁱⁱ—Zn1—O5—C7	−87.2 (5)	C9—N1—C7—O5	−177.9 (4)
Zn1ⁱ—O2—C1—O1	0.4 (5)	C9'—N1—C7—O5	4 (2)
Zn1ⁱ—O2—C1—C2	−179.1 (2)	C10'—N1—C7—C8	2.5 (8)
Zn1—O1—C1—O2	−1.0 (5)	C10—N1—C7—C8	−175.9 (5)
Zn1—O1—C1—C2	178.6 (2)	C7'—N1—C7—C8	−175.9 (8)
O2—C1—C2—C3	178.1 (4)	C9—N1—C7—C8	1.5 (6)
O1—C1—C2—C3	−1.4 (5)	C9'—N1—C7—C8	−176 (2)
O2—C1—C2—S1	2.6 (4)	C7—O5—C7'—N1	5.3 (7)
O1—C1—C2—S1	−176.9 (3)	Zn1—O5—C7'—N1	−172.9 (4)
C5—S1—C2—C3	5.4 (3)	C7—O5—C7'—C8'	−174.9 (11)
C5—S1—C2—C1	−178.5 (3)	Zn1—O5—C7'—C8'	7 (2)
C1—C2—C3—C4	179.1 (4)	C10'—N1—C7'—O5	−7.2 (17)
S1—C2—C3—C4	−5.0 (5)	C10—N1—C7'—O5	175.0 (12)
C2—C3—C4—C5	1.7 (6)	C7—N1—C7'—O5	−5.1 (7)
C3—C4—C5—C6	174.0 (4)	C9—N1—C7'—O5	−16 (4)
C3—C4—C5—S1	2.4 (5)	C9'—N1—C7'—O5	174.8 (10)
C2—S1—C5—C4	−4.4 (3)	C10'—N1—C7'—C8'	173.1 (12)
C2—S1—C5—C6	−176.4 (3)	C10—N1—C7'—C8'	−4.8 (11)
Zn1^v—O4—C6—O3	−5.8 (5)	C7—N1—C7'—C8'	175.2 (15)
Zn1^v—O4—C6—C5	171.8 (2)	C9—N1—C7'—C8'	164 (2)
Zn1^iv—O3—C6—O4	4.4 (6)	C9'—N1—C7'—C8'	−5.0 (14)
Zn1^iv—O3—C6—C5	−173.1 (2)

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

Experimental details

Crystal data
Chemical formula	[Zn₂(C₆H₂O₄S)₂(C₄H₉NO)₂]
M_r	645.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	153
a, b, c (Å)	8.4866 (2), 14.8476 (4), 10.1406 (3)
β (°)	100.734 (2)
V (Å³)	1255.41 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.13
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Gemini S Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.675, 0.815
No. of measured, independent and observed [I > 2σ(I)] reflections	7660, 2841, 1990
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.089, 0.93
No. of reflections	2841
No. of parameters	182
No. of restraints	5
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.55

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
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Wu, S.-M., Li, M., Xiang, J.-F., Yuan, L.-J. & Sun, J.-T. (2006). Acta Cryst. E62, o2951–o2952. Web of Science CSD CrossRef IUCr Journals Google Scholar

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