(Dimethyl sulfoxide-κO)trimeth-yl(2-methyl-3,5-dinitro-benzoato-κO)tin(IV).

In the title mononuclear complex, [Sn(CH(3))(3)(C(7)H(5)N(2)O(6))(C(2)H(6)OS)], 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 inter-molecular inter-action 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 = 467.06

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.144

S = 1.01

4500 reflections

242 parameters

4 restraints

H-atom parameters constrained

Δρmax = 1.55 e Å−3

Δρmin = −1.86 e Å−3

Data collection: KM-4 Software (Kuma, 1996 ▶); cell refinement: KM-4 Software; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022240/lh5258sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn(CH3)3(C7H5N2O6)(C2H6OS)]	F(000) = 936
Mr = 467.06	Dx = 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

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

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(Fo2) + (0.0947P)2] where P = (Fo2 + 2Fc2)/3
4500 reflections	(Δ/σ)max = 0.001
242 parameters	Δρmax = 1.55 e Å−3
4 restraints	Δρmin = −1.86 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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

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

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) .