Di-μ2-isopropano­lato-octa­methyl­bis­(μ-4-methyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-ido-κ2N1:N2)di-μ3-oxido-tetra­tin(IV)

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S160053681204771X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1546

doi:10.1107/S160053681204771X

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Di-μ₂-isopropanolato-octamethylbis(μ-4-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-ido-κ²N¹:N²)di-μ₃-oxido-tetratin(IV)

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 17 November 2012; accepted 20 November 2012; online 28 November 2012)

The tetranuclear title compound, [Sn₄(CH₃)₈(C₃H₇O)₂O₂(C₃H₄N₃S)₂], lies about a center of inversion; the molecule features a three-rung-staircase Sn₄O₄ core in which two Sn^IV atoms are bridged by the 4-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-ide group. The negatively charged N atom of the group binds to the terminal Sn^IV atom at a shorter distance [Sn—N = 2.236 (2) Å] compared with the neutral N atom that binds to the central Sn^IV atom [Sn← N = 2.805 (2) Å]. The terminal Sn^IV atom is five-coordinate in a cis-C₂SnNO₂ trigonal–bipyramidal geometry [C—Sn—C = 136.4 (1)°], whereas the central Sn^IV atom is six-coordinate in a C₂SnNO₃ skew-trazepoidal bipyramidal geometry [C—Sn—C = 145.4 (1)°]. The C atoms of the isopropoxy group are disordered over two positions in a 0.591 (7):0.409 (7) ratio.

Related literature

For the [Sn₂O(CH₃)₄(CH₃O)(C₃H₄N₃S)]₂ homolog, see: Najafi et al. (2011 ).

Experimental

Crystal data

[Sn₄(CH₃)₈(C₃H₇O)₂O₂(C₃H₄N₃S)₂]
M_r = 973.51
Monoclinic, P 2₁ /c
a = 9.6009 (4) Å
b = 10.0839 (4) Å
c = 18.3971 (6) Å
β = 94.667 (4)°
V = 1775.20 (12) Å³
Z = 2
Mo Kα radiation
μ = 2.93 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.474, T_max = 0.592
17413 measured reflections
4093 independent reflections
3613 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.052
S = 1.04
4093 reflections
174 parameters
21 restraints
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012); 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/S160053681204771X/bt6864sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204771X/bt6864Isup2.hkl

checkCIF report

Comment top

The title compound (Scheme I, Fig. 1), a distannoxane, was the unexpected product from an attempt at synthesizing a dimethyltin 4-methyl-4H-1,2,4-triazol-3-thiolate that possesses a tin-sulfur linkage. In the reaction of diorganotin oxides with organic acids (particularly carboxylic acids), tetranuclear distannoxanes are sometimes formed; these compounds have four organic groups. In the present reaction, two of the four organic groups are replaced by ethoxide groups.

Tetranuclear Sn₄O₂(CH₃)₈(C₃H₇O)₂(C₃H₄N₃S)₂ lies about a center-of-inversion; the molecule features a three-rung-staircase Sn₄O₄ core in which two Sn atoms are bridged by the C₃H₄N₃S triazolate group. The negatively-charged N atom of the group binds to the terminal Sn atom at a shorter distance [Sn–N 2.236 (2) Å] compared with the neutral N atom that binds to the central Sn atom [Sn←N 2.805 (2) Å]. The terminal Sn atom is five-coordinate in a cis-C₃SnNO trigonal bipyramid whereas the central Sn atom is six-coordinate in a C₂SnNO₃ skew-trazepoidal bipyramidal geometry.

Related literature top

For the [Sn₂O(CH₃)₄(CH₃O)(C₃H₄N₃S)]₂ homolog, see: Najafi et al. (2011).

Experimental top

Dimethyltin diisothiocyanate (1 mmol), 4-methyl-4H-1,2,4-triazole-3-thiol (1 mmol) and 1,10-phenanthroline (1 mmol) were loaded into a convection tube; several drops of triethylamine were added. The tube was filled with dry 2-propanol and kept at 333 K. Colorless crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 Sn₄O₂(CH₃)₈(C₃H₇O)₂(C₃H₄N₃S)₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

Di-µ₂-isopropanolato-octamethylbis(µ-4-methyl-5-sulfanylidene-4,5-dihydro- 1H-1,2,4-triazol-1-ido-κ²N¹:N²)di-µ₃-oxido- tetratin(IV) top

Crystal data top

[Sn₄(CH₃)₈(C₃H₇O)₂O₂(C₃H₄N₃S)₂]	F(000) = 944
M_r = 973.51	D_x = 1.821 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6879 reflections
a = 9.6009 (4) Å	θ = 3.1–27.5°
b = 10.0839 (4) Å	µ = 2.93 mm⁻¹
c = 18.3971 (6) Å	T = 100 K
β = 94.667 (4)°	Prism, colorless
V = 1775.20 (12) Å³	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	4093 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3613 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.1°
ω scan	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→12
T_min = 0.474, T_max = 0.592	l = −23→23
17413 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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.052	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0181P)² + 1.4453P] where P = (F_o² + 2F_c²)/3
4093 reflections	(Δ/σ)_max = 0.003
174 parameters	Δρ_max = 0.55 e Å⁻³
21 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Sn₄(CH₃)₈(C₃H₇O)₂O₂(C₃H₄N₃S)₂]	V = 1775.20 (12) Å³
M_r = 973.51	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6009 (4) Å	µ = 2.93 mm⁻¹
b = 10.0839 (4) Å	T = 100 K
c = 18.3971 (6) Å	0.30 × 0.25 × 0.20 mm
β = 94.667 (4)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	4093 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3613 reflections with I > 2σ(I)
T_min = 0.474, T_max = 0.592	R_int = 0.038
17413 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	21 restraints
wR(F²) = 0.052	H-atom parameters constrained
S = 1.04	Δρ_max = 0.55 e Å⁻³
4093 reflections	Δρ_min = −0.49 e Å⁻³
174 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.652613 (19)	0.422511 (18)	0.513713 (9)	0.01404 (6)
Sn2	0.52915 (2)	0.709776 (19)	0.634092 (9)	0.01671 (6)
S1	0.77775 (9)	0.79225 (8)	0.78514 (4)	0.02858 (18)
O1	0.5301 (2)	0.57582 (19)	0.55360 (9)	0.0169 (4)
O2	0.3284 (2)	0.7351 (2)	0.57053 (11)	0.0276 (5)
N1	0.8106 (3)	0.5270 (2)	0.63540 (12)	0.0203 (5)
N2	0.7409 (2)	0.6280 (2)	0.66839 (11)	0.0177 (5)
N3	0.9416 (2)	0.6003 (2)	0.73020 (12)	0.0190 (5)
C1	0.6250 (4)	0.2782 (3)	0.59418 (17)	0.0299 (7)
H1A	0.6127	0.3221	0.6408	0.045*
H1B	0.7074	0.2206	0.5995	0.045*
H1C	0.5421	0.2248	0.5797	0.045*
C2	0.7985 (3)	0.5418 (3)	0.46418 (15)	0.0246 (7)
H2A	0.8123	0.6249	0.4914	0.037*
H2B	0.7633	0.5614	0.4138	0.037*
H2C	0.8877	0.4946	0.4643	0.037*
C3	0.6090 (4)	0.8948 (3)	0.60284 (19)	0.0347 (8)
H3A	0.5315	0.9526	0.5850	0.052*
H3B	0.6718	0.8814	0.5641	0.052*
H3C	0.6607	0.9363	0.6450	0.052*
C4	0.4407 (3)	0.6321 (4)	0.72647 (15)	0.0320 (8)
H4A	0.3414	0.6558	0.7245	0.048*
H4B	0.4893	0.6692	0.7708	0.048*
H4C	0.4503	0.5354	0.7270	0.048*
C5	0.8202 (3)	0.6727 (3)	0.72657 (14)	0.0191 (6)
C6	1.0595 (3)	0.6163 (4)	0.78449 (16)	0.0287 (7)
H6A	1.1257	0.5433	0.7801	0.043*
H6B	1.0259	0.6153	0.8334	0.043*
H6C	1.1062	0.7009	0.7766	0.043*
C7	0.9295 (3)	0.5128 (3)	0.67331 (15)	0.0231 (6)
H7	0.9990	0.4500	0.6629	0.028*
C8	0.2044 (6)	0.7853 (7)	0.5959 (3)	0.0377 (16)	0.591 (7)
H8	0.1592	0.7218	0.6285	0.045*	0.591 (7)
C9	0.1067 (12)	0.8255 (19)	0.5272 (8)	0.038 (3)	0.591 (7)
H9A	0.0934	0.7491	0.4944	0.058*	0.591 (7)
H9B	0.1497	0.8983	0.5017	0.058*	0.591 (7)
H9C	0.0161	0.8542	0.5424	0.058*	0.591 (7)
C10	0.242 (2)	0.9267 (11)	0.6349 (6)	0.049 (3)	0.591 (7)
H10A	0.3190	0.9148	0.6726	0.074*	0.591 (7)
H10B	0.1597	0.9605	0.6572	0.074*	0.591 (7)
H10C	0.2697	0.9901	0.5984	0.074*	0.591 (7)
C8'	0.2376 (9)	0.8453 (9)	0.5658 (5)	0.0377 (16)	0.41
H8'	0.2723	0.9185	0.5353	0.045*	0.409 (7)
C9'	0.0850 (17)	0.802 (3)	0.5403 (13)	0.038 (3)	0.41
H9D	0.0874	0.7225	0.5100	0.058*	0.409 (7)
H9E	0.0381	0.8740	0.5119	0.058*	0.409 (7)
H9F	0.0337	0.7833	0.5830	0.058*	0.409 (7)
C10'	0.222 (3)	0.8905 (19)	0.6497 (8)	0.049 (3)	0.41
H10D	0.3053	0.8620	0.6804	0.074*	0.409 (7)
H10E	0.1390	0.8495	0.6673	0.074*	0.409 (7)
H10F	0.2140	0.9872	0.6520	0.074*	0.409 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01409 (10)	0.01444 (11)	0.01334 (9)	0.00295 (7)	−0.00045 (7)	−0.00018 (7)
Sn2	0.01739 (10)	0.01539 (11)	0.01707 (10)	0.00134 (7)	−0.00036 (8)	−0.00515 (7)
S1	0.0253 (4)	0.0286 (5)	0.0312 (4)	−0.0025 (3)	−0.0012 (3)	−0.0154 (3)
O1	0.0166 (10)	0.0185 (11)	0.0149 (9)	0.0055 (8)	−0.0037 (8)	−0.0056 (7)
O2	0.0232 (11)	0.0292 (13)	0.0288 (11)	0.0121 (10)	−0.0074 (9)	−0.0140 (9)
N1	0.0213 (13)	0.0218 (14)	0.0179 (11)	0.0058 (10)	0.0015 (10)	−0.0026 (10)
N2	0.0180 (12)	0.0163 (13)	0.0185 (11)	0.0013 (10)	−0.0003 (10)	−0.0041 (9)
N3	0.0151 (12)	0.0247 (14)	0.0167 (11)	−0.0040 (10)	−0.0009 (9)	0.0004 (9)
C1	0.0340 (18)	0.0247 (18)	0.0297 (16)	−0.0028 (14)	−0.0043 (14)	0.0093 (13)
C2	0.0203 (15)	0.0321 (19)	0.0217 (14)	−0.0023 (13)	0.0037 (12)	0.0051 (13)
C3	0.041 (2)	0.0187 (18)	0.0428 (19)	−0.0071 (15)	−0.0072 (16)	0.0056 (14)
C4	0.0277 (17)	0.048 (2)	0.0213 (15)	−0.0071 (16)	0.0084 (13)	−0.0066 (14)
C5	0.0172 (14)	0.0211 (16)	0.0188 (13)	−0.0040 (12)	0.0005 (11)	0.0005 (11)
C6	0.0181 (15)	0.039 (2)	0.0281 (15)	−0.0024 (14)	−0.0070 (13)	0.0017 (14)
C7	0.0211 (15)	0.0291 (18)	0.0195 (13)	0.0050 (13)	0.0029 (12)	−0.0025 (12)
C8	0.029 (3)	0.041 (4)	0.042 (4)	0.015 (3)	−0.006 (2)	−0.018 (2)
C9	0.024 (4)	0.034 (6)	0.056 (5)	0.016 (3)	−0.004 (4)	−0.009 (4)
C10	0.045 (5)	0.039 (7)	0.063 (5)	0.021 (5)	−0.009 (4)	−0.030 (5)
C8'	0.029 (3)	0.041 (4)	0.042 (4)	0.015 (3)	−0.006 (2)	−0.018 (2)
C9'	0.024 (4)	0.034 (6)	0.056 (5)	0.016 (3)	−0.004 (4)	−0.009 (4)
C10'	0.045 (5)	0.039 (7)	0.063 (5)	0.021 (5)	−0.009 (4)	−0.030 (5)

Geometric parameters (Å, º) top

Sn1—O1ⁱ	2.0633 (18)	C3—H3A	0.9800
Sn1—C1	2.108 (3)	C3—H3B	0.9800
Sn1—C2	2.109 (3)	C3—H3C	0.9800
Sn1—O1	2.1101 (18)	C4—H4A	0.9800
Sn1—O2ⁱ	2.2377 (19)	C4—H4B	0.9800
Sn1—N1	2.805 (2)	C4—H4C	0.9800
Sn2—O1	2.0050 (17)	C6—H6A	0.9800
Sn2—C4	2.111 (3)	C6—H6B	0.9800
Sn2—C3	2.115 (3)	C6—H6C	0.9800
Sn2—O2	2.187 (2)	C7—H7	0.9500
Sn2—N2	2.236 (2)	C8—C9	1.566 (9)
S1—C5	1.689 (3)	C8—C10	1.623 (9)
O1—Sn1ⁱ	2.0633 (18)	C8—H8	1.0000
O2—C8	1.408 (5)	C9—H9A	0.9800
O2—C8'	1.411 (7)	C9—H9B	0.9800
O2—Sn1ⁱ	2.2377 (19)	C9—H9C	0.9800
N1—C7	1.296 (4)	C10—H10A	0.9800
N1—N2	1.386 (3)	C10—H10B	0.9800
N2—C5	1.340 (3)	C10—H10C	0.9800
N3—C7	1.367 (4)	C8'—C9'	1.563 (11)
N3—C5	1.372 (4)	C8'—C10'	1.629 (10)
N3—C6	1.456 (3)	C8'—H8'	1.0000
C1—H1A	0.9800	C9'—H9D	0.9800
C1—H1B	0.9800	C9'—H9E	0.9800
C1—H1C	0.9800	C9'—H9F	0.9800
C2—H2A	0.9800	C10'—H10D	0.9800
C2—H2B	0.9800	C10'—H10E	0.9800
C2—H2C	0.9800	C10'—H10F	0.9800

O1ⁱ—Sn1—C1	106.13 (11)	Sn2—C3—H3C	109.5
O1ⁱ—Sn1—C2	107.34 (10)	H3A—C3—H3C	109.5
C1—Sn1—C2	145.41 (12)	H3B—C3—H3C	109.5
O1ⁱ—Sn1—O1	74.45 (8)	Sn2—C4—H4A	109.5
C1—Sn1—O1	98.98 (11)	Sn2—C4—H4B	109.5
C2—Sn1—O1	98.10 (10)	H4A—C4—H4B	109.5
O1ⁱ—Sn1—O2ⁱ	72.74 (7)	Sn2—C4—H4C	109.5
C1—Sn1—O2ⁱ	91.03 (11)	H4A—C4—H4C	109.5
C2—Sn1—O2ⁱ	90.66 (11)	H4B—C4—H4C	109.5
O1—Sn1—O2ⁱ	147.18 (7)	N2—C5—N3	106.6 (2)
O1ⁱ—Sn1—N1	148.65 (7)	N2—C5—S1	126.7 (2)
C1—Sn1—N1	77.85 (10)	N3—C5—S1	126.6 (2)
C2—Sn1—N1	78.21 (9)	N3—C6—H6A	109.5
O1—Sn1—N1	74.22 (7)	N3—C6—H6B	109.5
O2ⁱ—Sn1—N1	138.60 (7)	H6A—C6—H6B	109.5
O1—Sn2—C4	111.77 (11)	N3—C6—H6C	109.5
O1—Sn2—C3	111.73 (11)	H6A—C6—H6C	109.5
C4—Sn2—C3	136.43 (14)	H6B—C6—H6C	109.5
O1—Sn2—O2	74.96 (7)	N1—C7—N3	110.9 (3)
C4—Sn2—O2	94.53 (11)	N1—C7—H7	124.5
C3—Sn2—O2	94.29 (11)	N3—C7—H7	124.5
O1—Sn2—N2	84.34 (8)	O2—C8—C9	106.9 (8)
C4—Sn2—N2	92.98 (11)	O2—C8—C10	107.4 (8)
C3—Sn2—N2	93.49 (12)	C9—C8—C10	103.1 (10)
O2—Sn2—N2	159.29 (8)	O2—C8—H8	112.9
Sn2—O1—Sn1ⁱ	112.53 (9)	C9—C8—H8	112.9
Sn2—O1—Sn1	141.87 (9)	C10—C8—H8	112.9
Sn1ⁱ—O1—Sn1	105.55 (8)	C8—C9—H9A	109.5
C8—O2—Sn2	126.6 (3)	C8—C9—H9B	109.5
C8'—O2—Sn2	129.7 (4)	H9A—C9—H9B	109.5
C8—O2—Sn1ⁱ	127.2 (3)	C8—C9—H9C	109.5
C8'—O2—Sn1ⁱ	126.9 (4)	H9A—C9—H9C	109.5
Sn2—O2—Sn1ⁱ	99.75 (8)	H9B—C9—H9C	109.5
C7—N1—N2	106.3 (2)	C8—C10—H10A	109.5
C7—N1—Sn1	141.58 (19)	C8—C10—H10B	109.5
N2—N1—Sn1	112.10 (15)	H10A—C10—H10B	109.5
C5—N2—N1	109.5 (2)	C8—C10—H10C	109.5
C5—N2—Sn2	123.10 (19)	H10A—C10—H10C	109.5
N1—N2—Sn2	127.45 (16)	H10B—C10—H10C	109.5
C7—N3—C5	106.7 (2)	O2—C8'—C9'	111.1 (13)
C7—N3—C6	127.5 (3)	O2—C8'—C10'	105.3 (11)
C5—N3—C6	125.8 (2)	C9'—C8'—C10'	102.0 (16)
Sn1—C1—H1A	109.5	O2—C8'—H8'	112.6
Sn1—C1—H1B	109.5	C9'—C8'—H8'	112.6
H1A—C1—H1B	109.5	C10'—C8'—H8'	112.6
Sn1—C1—H1C	109.5	C8'—C9'—H9D	109.5
H1A—C1—H1C	109.5	C8'—C9'—H9E	109.5
H1B—C1—H1C	109.5	H9D—C9'—H9E	109.5
Sn1—C2—H2A	109.5	C8'—C9'—H9F	109.5
Sn1—C2—H2B	109.5	H9D—C9'—H9F	109.5
H2A—C2—H2B	109.5	H9E—C9'—H9F	109.5
Sn1—C2—H2C	109.5	C8'—C10'—H10D	109.5
H2A—C2—H2C	109.5	C8'—C10'—H10E	109.5
H2B—C2—H2C	109.5	H10D—C10'—H10E	109.5
Sn2—C3—H3A	109.5	C8'—C10'—H10F	109.5
Sn2—C3—H3B	109.5	H10D—C10'—H10F	109.5
H3A—C3—H3B	109.5	H10E—C10'—H10F	109.5

C4—Sn2—O1—Sn1ⁱ	87.73 (13)	O1—Sn1—N1—N2	1.24 (17)
C3—Sn2—O1—Sn1ⁱ	−89.81 (13)	O2ⁱ—Sn1—N1—N2	−179.37 (16)
O2—Sn2—O1—Sn1ⁱ	−1.17 (9)	C7—N1—N2—C5	−0.3 (3)
N2—Sn2—O1—Sn1ⁱ	178.69 (11)	Sn1—N1—N2—C5	179.15 (17)
C4—Sn2—O1—Sn1	−88.87 (19)	C7—N1—N2—Sn2	179.8 (2)
C3—Sn2—O1—Sn1	93.60 (19)	Sn1—N1—N2—Sn2	−0.7 (3)
O2—Sn2—O1—Sn1	−177.76 (18)	O1—Sn2—N2—C5	179.9 (2)
N2—Sn2—O1—Sn1	2.09 (16)	C4—Sn2—N2—C5	−68.5 (2)
O1ⁱ—Sn1—O1—Sn2	176.7 (2)	C3—Sn2—N2—C5	68.4 (2)
C1—Sn1—O1—Sn2	72.38 (18)	O2—Sn2—N2—C5	−179.7 (2)
C2—Sn1—O1—Sn2	−77.43 (18)	O1—Sn2—N2—N1	−0.2 (2)
O2ⁱ—Sn1—O1—Sn2	178.55 (13)	C4—Sn2—N2—N1	111.4 (2)
N1—Sn1—O1—Sn2	−2.19 (15)	C3—Sn2—N2—N1	−111.8 (2)
O1ⁱ—Sn1—O1—Sn1ⁱ	0.0	O2—Sn2—N2—N1	0.2 (4)
C1—Sn1—O1—Sn1ⁱ	−104.36 (11)	N1—N2—C5—N3	0.5 (3)
C2—Sn1—O1—Sn1ⁱ	105.84 (11)	Sn2—N2—C5—N3	−179.64 (17)
O2ⁱ—Sn1—O1—Sn1ⁱ	1.82 (19)	N1—N2—C5—S1	−178.2 (2)
N1—Sn1—O1—Sn1ⁱ	−178.92 (10)	Sn2—N2—C5—S1	1.6 (4)
O1—Sn2—O2—C8	154.1 (4)	C7—N3—C5—N2	−0.5 (3)
C4—Sn2—O2—C8	42.7 (4)	C6—N3—C5—N2	179.2 (3)
C3—Sn2—O2—C8	−94.6 (4)	C7—N3—C5—S1	178.3 (2)
N2—Sn2—O2—C8	153.7 (4)	C6—N3—C5—S1	−2.1 (4)
O1—Sn2—O2—C8'	−158.3 (6)	N2—N1—C7—N3	0.0 (3)
C4—Sn2—O2—C8'	90.3 (6)	Sn1—N1—C7—N3	−179.2 (2)
C3—Sn2—O2—C8'	−47.0 (6)	C5—N3—C7—N1	0.3 (3)
N2—Sn2—O2—C8'	−158.7 (6)	C6—N3—C7—N1	−179.4 (3)
O1—Sn2—O2—Sn1ⁱ	1.01 (8)	C8'—O2—C8—C9	52.9 (10)
C4—Sn2—O2—Sn1ⁱ	−110.34 (12)	Sn2—O2—C8—C9	162.6 (6)
C3—Sn2—O2—Sn1ⁱ	112.37 (12)	Sn1ⁱ—O2—C8—C9	−51.5 (9)
N2—Sn2—O2—Sn1ⁱ	0.6 (3)	C8'—O2—C8—C10	−57.2 (10)
O1ⁱ—Sn1—N1—C7	178.4 (3)	Sn2—O2—C8—C10	52.5 (8)
C1—Sn1—N1—C7	77.3 (3)	Sn1ⁱ—O2—C8—C10	−161.6 (5)
C2—Sn1—N1—C7	−77.5 (3)	C8—O2—C8'—C9'	−56.5 (13)
O1—Sn1—N1—C7	−179.6 (3)	Sn2—O2—C8'—C9'	−157.3 (11)
O2ⁱ—Sn1—N1—C7	−0.2 (4)	Sn1ⁱ—O2—C8'—C9'	48.5 (14)
O1ⁱ—Sn1—N1—N2	−0.8 (3)	C8—O2—C8'—C10'	53.2 (12)
C1—Sn1—N1—N2	−101.9 (2)	Sn2—O2—C8'—C10'	−47.6 (13)
C2—Sn1—N1—N2	103.28 (19)	Sn1ⁱ—O2—C8'—C10'	158.2 (10)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn₄(CH₃)₈(C₃H₇O)₂O₂(C₃H₄N₃S)₂]
M_r	973.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.6009 (4), 10.0839 (4), 18.3971 (6)
β (°)	94.667 (4)
V (Å³)	1775.20 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.93
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.474, 0.592
No. of measured, independent and observed [I > 2σ(I)] reflections	17413, 4093, 3613
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.052, 1.04
No. of reflections	4093
No. of parameters	174
No. of restraints	21
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.49

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank Shahid Beheshti University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m242. Web of Science CSD CrossRef IUCr Journals 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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