(Dimethyl sulfoxide-κO)trimeth­yl(2-methyl-3,5-dinitro­benzoato-κO1)tin(IV)

Danish, M.; Ghafoor, S.; Ahmad, N.; Starosta, W.; Leciejewicz, J.

doi:10.1107/S1600536811022240

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m923

doi:10.1107/S1600536811022240

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(Dimethyl sulfoxide-κO)trimethyl(2-methyl-3,5-dinitrobenzoato-κO¹)tin(IV)

Muhammed Danish,^a ^* Sabiha Ghafoor,^b Nazir Ahmad,^b Wojciech Starosta ^c and Janusz Leciejewicz ^c

^aDepartment of Chemistry, University of Gujrat, Hafiz Hayat Campus, Gujrat 50700, Pakistan, ^bDepartment of Chemistry, University of Sargodha, Sargodha 40100, Pakistan, and ^cInstitute of Nuclear Chemistry and Technology, ul. Dorodna 16, 03-195 Warszawa, Poland
^*Correspondence e-mail: drdanish62@gmail.com

(Received 23 May 2011; accepted 8 June 2011; online 18 June 2011)

In the title mononuclear complex, [Sn(CH₃)₃(C₇H₅N₂O₆)(C₂H₆OS)], the Sn^IV ion is coordinated by three methyl groups in the equatorial plane, and by an O atom from a 2-methyl-3,5-dinitrobenzoate ligand and a dimethyl sulfoxide ligand in the axial sites, to form a slightly distorted trigonal–bipyramidal environment. The O atoms of one of the nitro groups are disordered over two sets of sites, with refined occupancies of 0.55 (4) and 0.45 (4). The closest intermolecular interaction is a weak C—H⋯O hydrogen bond.

Related literature

For the applications of trimethytin complexes, see: Gielen et al. (2005 ); Gielen (2002 ); Hameed et al. (2009 ); Ashhad et al. (2005 ). For the structure of a trimethyltin complex with a 2-methylbenzene-3-carboxylate ligand, see: Danish et al. (2010 ). For the structure of a triphenyltin complex with 2-methyl-3,5-dinitrobenzene carboxylate and methanol ligands, see: Danish et al. (2011 ).

Experimental

Crystal data

[Sn(CH₃)₃(C₇H₅N₂O₆)(C₂H₆OS)]
M_r = 467.06
Monoclinic, P 2₁ /c
a = 9.6180 (19) Å
b = 12.971 (3) Å
c = 15.612 (3) Å
β = 102.98 (3)°
V = 1897.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.49 mm⁻¹
T = 293 K
0.42 × 0.24 × 0.08 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.753, T_max = 0.890
4755 measured reflections
4500 independent reflections
2464 reflections with I > 2σ(I)
R_int = 0.030
3 standard reflections every 200 reflections intensity decay: 0.2%

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.144
S = 1.01
4500 reflections
242 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 1.55 e Å⁻³
Δρ_min = −1.86 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11C⋯O3ⁱ	0.96	2.59	3.509 (15)	162
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: KM-4 Software (Kuma, 1996 $[Kuma (1996). KM-4 Software. Kuma Diffraction Ltd, Wrocław, Poland.]$ ); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 $[Kuma (2001). DATAPROC. Kuma Diffraction Ltd, Wrocław, Poland.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811022240/lh5258sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022240/lh5258Isup2.hkl

checkCIF report

Comment top

Organotin carboxylates are extensively studied bexcause of their potential diversified biological applications. Trimethyltin carboxylates find use as antifungal (Gielen et al., 2005; Gielen, 2002) and antibacterial agents (Hameed et al., 2009; Ashhad et al., 2005). The title compound is part of our continued effort in this area (Danish et al., 2010, 2011). The structure of the title compound is composed of mononuclear molecules in which an Sn atom is coordinated by three methyl C atoms, one carboxylato O atom donated by a 2-methyl-3,5-dinitrobenzenecarboxylate ligand and an O atom from a DMSO ligand forming slightly distorted trigonal bipyramidal environment. The methyl C atoms form the equatorial plane. The Sn atom is displaced by 0.1082 (2) Å from the plane towards the carboxylate O atom. The latter and the DMSO O atom are in the axial sites. The Sn—C bond lengths range from 2.097 (3) to 2.121 (3) Å and are close to those reported earlier in the structures of other trimethyltin complexes (e.g. Danish et al., 2010). The 2-methyl-3,5-dintro-benzenecarboxylate ligand molecule is essentially planar with an r.m.s. deviation of 0.0041 (1) Å. The O atoms of one of the nitro groups show positional disorder with a major component occupancy of 0.55 (4). The other nitro group forms a dihedral angle of 5.9 (2)° with the methylbenzene ring. The carboxylate group donates a single O atom to the Sn atom. The observed Sn—O bond length of 2.106 (3) Å is typical (e.g. Danish et al., 2010, 2011). The closest intermolecular interaction is a weak C—H···O hydrogen bond.

Related literature top

For the applications of trimethytin complexes, see: Gielen et al. (2005); Gielen (2002); Hameed et al. (2009); Ashhad et al. (2005). For the structure of a trimethyltin complex with a 2-methylbenzene-3-carboxylate ligand, see: Danish et al. (2010). For the structure of a triphenyltin complex with 2-methyl-3,5-dinitrobenzene carboxylate and methanol ligands, see: Danish et al. (2011).

Experimental top

The sodium salt of 3,5-dinitro-o-toluic acid (2.48 g, 0.01 mol) was suspended in 25 ml of dry chloroform contained in a 100 ml round-bottom flask; trimethyltin chloride (2.00 g, 0.01 mol) was dissolved in 25 ml of dry chloroform was then added dropwise with constant stirring at room temperature. The reaction mixture was then refluxed in chloroform for 6 h and then brought to room temperature. Filtration was carried out to remove sodium chloride formed during the reaction. After evaporation, the solid mass was recrystallized from DMSO. m.p. 395 K; yield 88%.

Computing details top

Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software (Kuma, 1996); data reduction: DATAPROC (Kuma, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure with 50% probability displacement ellipsoids. Atoms labeled O3A and O4A are the minor components of disorder.

(Dimethyl sulfoxide-κO)trimethyl(2-methyl- 3,5-dinitrobenzoato-κO¹)tin(IV) top

Crystal data top

[Sn(CH₃)₃(C₇H₅N₂O₆)(C₂H₆OS)]	F(000) = 936
M_r = 467.06	D_x = 1.635 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.6180 (19) Å	θ = 6–15°
b = 12.971 (3) Å	µ = 1.49 mm⁻¹
c = 15.612 (3) Å	T = 293 K
β = 102.98 (3)°	Plate, pale yellow
V = 1897.9 (7) Å³	0.42 × 0.24 × 0.08 mm
Z = 4

Data collection top

Kuma KM-4 four-circle diffractometer	2464 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 28.0°, θ_min = 2.1°
Profile data from ω/2θ scans	h = 0→12
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = 0→17
T_min = 0.753, T_max = 0.890	l = −19→19
4755 measured reflections	3 standard reflections every 200 reflections
4500 independent reflections	intensity decay: 0.2%

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0947P)²] where P = (F_o² + 2F_c²)/3
4500 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 1.55 e Å⁻³
4 restraints	Δρ_min = −1.86 e Å⁻³

Crystal data top

[Sn(CH₃)₃(C₇H₅N₂O₆)(C₂H₆OS)]	V = 1897.9 (7) Å³
M_r = 467.06	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6180 (19) Å	µ = 1.49 mm⁻¹
b = 12.971 (3) Å	T = 293 K
c = 15.612 (3) Å	0.42 × 0.24 × 0.08 mm
β = 102.98 (3)°

Data collection top

Kuma KM-4 four-circle diffractometer	2464 reflections with I > 2σ(I)
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	R_int = 0.030
T_min = 0.753, T_max = 0.890	3 standard reflections every 200 reflections
4755 measured reflections	intensity decay: 0.2%
4500 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.01	Δρ_max = 1.55 e Å⁻³
4500 reflections	Δρ_min = −1.86 e Å⁻³
242 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	Occ. (<1)
Sn1	0.78174 (3)	0.49914 (2)	0.21581 (2)	0.04452 (13)
S1	1.10224 (14)	0.53273 (12)	0.15598 (9)	0.0519 (3)
O1	0.6418 (4)	0.4762 (3)	0.3068 (3)	0.0605 (10)
C4	0.2430 (5)	0.4664 (4)	0.4708 (3)	0.0520 (11)
H4	0.1832	0.4573	0.5094	0.062*
C2	0.4266 (5)	0.3988 (4)	0.3974 (3)	0.0468 (11)
C5	0.2474 (5)	0.5571 (4)	0.4271 (3)	0.0464 (11)
C1	0.4264 (4)	0.4929 (3)	0.3564 (3)	0.0433 (9)
O5	0.0655 (5)	0.6244 (4)	0.4846 (3)	0.0929 (15)
N2	0.1513 (5)	0.6424 (4)	0.4406 (3)	0.0634 (11)
O2	0.4719 (4)	0.5782 (3)	0.2313 (3)	0.0696 (11)
C3	0.3313 (5)	0.3894 (4)	0.4546 (3)	0.0507 (11)
C6	0.3363 (5)	0.5725 (4)	0.3706 (3)	0.0460 (10)
H6	0.3364	0.6353	0.3420	0.055*
C8	0.5152 (7)	0.3080 (4)	0.3837 (4)	0.0719 (16)
H8A	0.4854	0.2844	0.3241	0.108*
H8B	0.5032	0.2535	0.4230	0.108*
H8C	0.6138	0.3278	0.3951	0.108*
O7	0.9437 (4)	0.5132 (3)	0.1204 (3)	0.0582 (9)
C11	0.8247 (6)	0.6531 (4)	0.2547 (4)	0.0705 (16)
H11A	0.7725	0.6982	0.2102	0.106*
H11B	0.9251	0.6662	0.2628	0.106*
H11C	0.7963	0.6651	0.3090	0.106*
C14	1.1886 (6)	0.4276 (5)	0.1203 (5)	0.080 (2)
H14A	1.2873	0.4442	0.1249	0.121*
H14B	1.1443	0.4123	0.0602	0.121*
H14C	1.1816	0.3686	0.1562	0.121*
C13	0.9183 (7)	0.3843 (5)	0.2860 (4)	0.0768 (18)
H13A	0.8622	0.3330	0.3070	0.115*
H13B	0.9831	0.4154	0.3350	0.115*
H13C	0.9714	0.3527	0.2478	0.115*
C15	1.1490 (7)	0.6276 (5)	0.0867 (5)	0.0784 (18)
H15A	1.1406	0.5995	0.0289	0.118*
H15B	1.2456	0.6492	0.1098	0.118*
H15C	1.0862	0.6857	0.0838	0.118*
C12	0.6354 (6)	0.4555 (6)	0.1006 (4)	0.0708 (15)
H12A	0.6211	0.5118	0.0597	0.106*
H12B	0.5461	0.4376	0.1146	0.106*
H12C	0.6719	0.3971	0.0749	0.106*
O6	0.1644 (5)	0.7246 (4)	0.4073 (4)	0.0974 (16)
C7	0.5190 (5)	0.5193 (4)	0.2909 (4)	0.0508 (12)
N1	0.3216 (6)	0.2921 (4)	0.5005 (3)	0.0681 (13)
O4A	0.2078 (17)	0.2483 (18)	0.4785 (18)	0.104 (8)	0.45 (4)
O3A	0.414 (3)	0.258 (2)	0.555 (3)	0.175 (15)	0.45 (4)
O4	0.287 (4)	0.2135 (11)	0.4607 (9)	0.128 (9)	0.55 (4)
O3	0.3585 (19)	0.2947 (11)	0.5794 (5)	0.084 (5)	0.55 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03448 (18)	0.0566 (2)	0.0461 (2)	0.00010 (14)	0.01663 (12)	0.00159 (15)
S1	0.0403 (6)	0.0702 (7)	0.0495 (7)	−0.0029 (6)	0.0192 (5)	−0.0052 (6)
O1	0.048 (2)	0.077 (2)	0.065 (2)	0.0068 (17)	0.0314 (17)	0.0058 (18)
C4	0.046 (3)	0.063 (3)	0.051 (3)	−0.011 (2)	0.020 (2)	−0.007 (2)
C2	0.035 (2)	0.054 (3)	0.053 (3)	−0.009 (2)	0.0140 (19)	−0.011 (2)
C5	0.031 (2)	0.057 (3)	0.054 (3)	−0.004 (2)	0.0159 (19)	−0.005 (2)
C1	0.0305 (19)	0.059 (3)	0.043 (2)	−0.0075 (19)	0.0135 (16)	−0.004 (2)
O5	0.076 (3)	0.111 (4)	0.114 (4)	0.020 (3)	0.067 (3)	0.008 (3)
N2	0.051 (3)	0.075 (3)	0.069 (3)	0.008 (2)	0.024 (2)	−0.008 (2)
O2	0.056 (2)	0.093 (3)	0.067 (3)	0.011 (2)	0.0278 (19)	0.022 (2)
C3	0.044 (3)	0.058 (3)	0.054 (3)	−0.014 (2)	0.019 (2)	−0.004 (2)
C6	0.039 (2)	0.056 (3)	0.046 (3)	−0.004 (2)	0.018 (2)	0.000 (2)
C8	0.068 (4)	0.062 (3)	0.096 (4)	0.001 (3)	0.040 (3)	−0.002 (3)
O7	0.0427 (18)	0.085 (3)	0.053 (2)	−0.0081 (16)	0.0236 (15)	−0.0030 (17)
C11	0.063 (4)	0.070 (4)	0.085 (4)	−0.011 (3)	0.029 (3)	−0.014 (3)
C14	0.049 (3)	0.074 (4)	0.123 (6)	0.010 (3)	0.029 (4)	0.003 (4)
C13	0.070 (4)	0.094 (4)	0.072 (4)	0.023 (3)	0.030 (3)	0.023 (3)
C15	0.064 (4)	0.069 (4)	0.111 (5)	−0.011 (3)	0.039 (3)	0.003 (4)
C12	0.048 (3)	0.105 (4)	0.062 (3)	−0.014 (3)	0.019 (3)	−0.018 (3)
O6	0.096 (4)	0.070 (3)	0.144 (5)	0.024 (3)	0.065 (3)	0.014 (3)
C7	0.041 (2)	0.063 (3)	0.056 (3)	−0.005 (2)	0.026 (2)	−0.001 (2)
N1	0.074 (4)	0.065 (3)	0.074 (4)	−0.020 (3)	0.035 (3)	−0.001 (3)
O4A	0.104 (11)	0.084 (11)	0.126 (15)	−0.031 (9)	0.030 (9)	0.033 (9)
O3A	0.099 (15)	0.084 (15)	0.29 (3)	−0.014 (10)	−0.067 (17)	0.097 (17)
O4	0.22 (2)	0.076 (7)	0.109 (8)	−0.068 (10)	0.075 (11)	−0.036 (6)
O3	0.116 (10)	0.063 (7)	0.073 (8)	−0.003 (6)	0.018 (6)	0.019 (4)

Geometric parameters (Å, º) top

Sn1—C12	2.097 (5)	C8—H8B	0.9600
Sn1—C11	2.101 (5)	C8—H8C	0.9600
Sn1—C13	2.121 (6)	C11—H11A	0.9600
Sn1—O1	2.186 (4)	C11—H11B	0.9600
Sn1—O7	2.391 (4)	C11—H11C	0.9600
S1—O7	1.523 (4)	C14—H14A	0.9600
S1—C14	1.752 (6)	C14—H14B	0.9600
S1—C15	1.761 (6)	C14—H14C	0.9600
O1—C7	1.280 (6)	C13—H13A	0.9600
C4—C5	1.366 (7)	C13—H13B	0.9600
C4—C3	1.371 (7)	C13—H13C	0.9600
C4—H4	0.9300	C15—H15A	0.9600
C2—C1	1.379 (6)	C15—H15B	0.9600
C2—C3	1.420 (7)	C15—H15C	0.9600
C2—C8	1.497 (7)	C12—H12A	0.9600
C5—C6	1.374 (6)	C12—H12B	0.9600
C5—N2	1.486 (6)	C12—H12C	0.9600
C1—C6	1.398 (6)	N1—O3A	1.174 (9)
C1—C7	1.537 (6)	N1—O3	1.205 (8)
O5—N2	1.210 (6)	N1—O4	1.201 (8)
N2—O6	1.205 (6)	N1—O4A	1.213 (8)
O2—C7	1.210 (6)	O4A—O4	0.981 (17)
C3—N1	1.464 (7)	O3A—O3	0.87 (4)
C6—H6	0.9300	O3A—O4	1.78 (2)
C8—H8A	0.9600

C12—Sn1—C11	123.7 (3)	H11B—C11—H11C	109.5
C12—Sn1—C13	118.2 (3)	S1—C14—H14A	109.5
C11—Sn1—C13	117.3 (3)	S1—C14—H14B	109.5
C12—Sn1—O1	97.35 (19)	H14A—C14—H14B	109.5
C11—Sn1—O1	92.95 (19)	S1—C14—H14C	109.5
C13—Sn1—O1	88.19 (19)	H14A—C14—H14C	109.5
C12—Sn1—O7	83.81 (18)	H14B—C14—H14C	109.5
C11—Sn1—O7	89.68 (18)	Sn1—C13—H13A	109.5
C13—Sn1—O7	87.77 (19)	Sn1—C13—H13B	109.5
O1—Sn1—O7	175.87 (12)	H13A—C13—H13B	109.5
O7—S1—C14	105.2 (3)	Sn1—C13—H13C	109.5
O7—S1—C15	105.4 (3)	H13A—C13—H13C	109.5
C14—S1—C15	98.3 (3)	H13B—C13—H13C	109.5
C7—O1—Sn1	119.4 (3)	S1—C15—H15A	109.5
C5—C4—C3	116.5 (5)	S1—C15—H15B	109.5
C5—C4—H4	121.7	H15A—C15—H15B	109.5
C3—C4—H4	121.7	S1—C15—H15C	109.5
C1—C2—C3	115.8 (4)	H15A—C15—H15C	109.5
C1—C2—C8	124.8 (4)	H15B—C15—H15C	109.5
C3—C2—C8	119.4 (5)	Sn1—C12—H12A	109.5
C4—C5—C6	122.6 (5)	Sn1—C12—H12B	109.5
C4—C5—N2	118.8 (4)	H12A—C12—H12B	109.5
C6—C5—N2	118.7 (4)	Sn1—C12—H12C	109.5
C2—C1—C6	121.1 (4)	H12A—C12—H12C	109.5
C2—C1—C7	124.5 (4)	H12B—C12—H12C	109.5
C6—C1—C7	114.4 (4)	O2—C7—O1	126.5 (5)
O6—N2—O5	124.6 (5)	O2—C7—C1	118.6 (4)
O6—N2—C5	117.9 (4)	O1—C7—C1	114.9 (5)
O5—N2—C5	117.5 (5)	O3A—N1—O3	43 (2)
C4—C3—C2	124.5 (5)	O3A—N1—O4	97.4 (14)
C4—C3—N1	115.3 (5)	O3—N1—O4	122.4 (10)
C2—C3—N1	120.2 (5)	O3A—N1—O4A	121.3 (13)
C5—C6—C1	119.5 (4)	O3—N1—O4A	110.0 (13)
C5—C6—H6	120.2	O4—N1—O4A	48.0 (8)
C1—C6—H6	120.2	O3A—N1—C3	124.0 (11)
C2—C8—H8A	109.5	O3—N1—C3	116.1 (7)
C2—C8—H8B	109.5	O4—N1—C3	121.3 (8)
H8A—C8—H8B	109.5	O4A—N1—C3	114.8 (8)
C2—C8—H8C	109.5	O4—O4A—N1	65.4 (8)
H8A—C8—H8C	109.5	O3—O3A—N1	70.4 (12)
H8B—C8—H8C	109.5	O3—O3A—O4	99.4 (19)
S1—O7—Sn1	121.6 (2)	N1—O3A—O4	41.9 (8)
Sn1—C11—H11A	109.5	O4A—O4—N1	66.6 (8)
Sn1—C11—H11B	109.5	O4A—O4—O3A	92.9 (14)
H11A—C11—H11B	109.5	N1—O4—O3A	40.7 (7)
Sn1—C11—H11C	109.5	O3A—O3—N1	66.6 (14)
H11A—C11—H11C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O3ⁱ	0.96	2.59	3.509 (15)	162

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(C₇H₅N₂O₆)(C₂H₆OS)]
M_r	467.06
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.6180 (19), 12.971 (3), 15.612 (3)
β (°)	102.98 (3)
V (Å³)	1897.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.49
Crystal size (mm)	0.42 × 0.24 × 0.08

Data collection
Diffractometer	Kuma KM-4 four-circle diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.753, 0.890
No. of measured, independent and observed [I > 2σ(I)] reflections	4755, 4500, 2464
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.144, 1.01
No. of reflections	4500
No. of parameters	242
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.55, −1.86

Computer programs: KM-4 Software (Kuma, 1996), DATAPROC (Kuma, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O3ⁱ	0.96	2.59	3.509 (15)	161.6

Symmetry code: (i) −x+1, −y+1, −z+1.

References

Ashhad, A. M. S., Islam, N. & Saeed, M. (2005). Malasiyan J. Pharm. Sci. 3, 11-18. Google Scholar
Danish, M., Saleem, I., Ahmad, N., Starosta, W. & Leciejewicz, J. (2010). Acta Cryst. E66, m4. Web of Science CSD CrossRef IUCr Journals Google Scholar
Danish, M., Ghafoor, S., Ahmad, N., Starosta, W. & Leciejewicz, J. (2011). Acta Cryst. E67, m519. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gielen, M. (2002). Appl. Organomet. Chem. 16, 481–486. CrossRef CAS Google Scholar
Gielen, M., Biesemans, M. & Wielem, M. (2005). J. Organomet. Chem. 19, 440–449. CrossRef CAS Google Scholar
Hameed, A., Mohamad, T., Elbay Saad, E., Farina, Y., Graisa, A. & Yousif, E. (2009). Eur. J. Sci. Res. pp. 212–217. Google Scholar
Kuma (1996). KM-4 Software. Kuma Diffraction Ltd, Wrocław, Poland. Google Scholar
Kuma (2001). DATAPROC. Kuma Diffraction Ltd, Wrocław, Poland. Google Scholar
Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page m923

doi:10.1107/S1600536811022240

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