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The Sn atom in the crystal structure of the title compound,catena-poly­[trimethyl­tin-μ-[(2,5-di­oxo-2,5-di­hydro­pyrrol-1-yl)­acetato-O:O′]], [Sn(CH3)3(C6H4NO4)], adopts a distorted trigonal bipyramidal coordination geometry with three methyl groups defining the trigonal plane [mean Sn—C 2.117 (11) Å] and the axial positions occupied by O atoms from different carboxylate groups, with significantly different Sn—O bond lengths [2.207 (5) and 2.358 (6) Å]. The structure forms a polymeric chain of complex molecules linked via carboxylate moieties.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199016510/fr1244sup1.cif
Contains datablocks Global, (I)

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199016510/fr1244Isup2.hkl
Contains datablock I

CCDC reference: 143240

Comment top

In the past two decades, organotin carboxylates have received much attention because of their extensive applications in different fields of life science (Davis et al., 1982; Tagliavini, 1992; Brimah et al., 1994), especially biocidal applications, utilizing the antitumour and anticancer activities of such compounds (Gielen et al., 1994; de Vos et al., 1998). Accordingly and in view of our continuous interest in the synthesis, characterization, biological applications and crystal structures of organotin carboxylates (Danish et al., 1995; Parvez et al., 1997, 1999, 2000), we have prepared a new organotin derivative of 2-maleimidoacetic acid, commonly known as N-maleoylglycine. In this paper we now report the crystal structure of (N-maleoylglycinato)trimethyltin(IV), (I).

The structure of (I) is presented in Fig. 1. The Sn atom is bonded to three methyl groups in the equatorial positions with Sn—C distances [mean 2.117 (11) Å] that are essentially equal within experimental uncertainty and that are in agreement with the values reported for related structures (Allen et al., 1983). The axial positions are occupied by O atoms from the carboxylate residues, with a nearly linear O—Sn—O angle of 172.90 (19)°. The intramolecular distance Sn1—O1 [2.207 (5) Å] is significantly shorter than the intermolecular distance Sn1—O2i [2.358 (6) Å; symmetry code: (i) 1 - x, 1/2 + y, 3/2 - z], indicating that the former is a covalent bond and the latter is a coordinate bond. The Sn atom has distorted trigonal bipyramidal coordination geometry with the Sn atom 0.084 (6) Å out of the equatorial plane formed by the three methyl C atoms, towards the more strongly bound O1 atom. This trend is in line with other similar structures reported by our laboratories, as mentioned above.

The molecular dimensions in the ligand, N-maleoylglycine, are normal, with the five-membered ring essentially planar [maximum deviation: N1 0.035 (5) Å], and slightly pyramidal geometry about N1. The structure is composed of infinite chains of (I) running along the b axis.

A few examples of crystal structures containing triorganotin complexes of protected compounds, forming polymeric chains similar to (I), are: (3-indolylacetato-O,O')tri-n-butyltin (Molloy et al.,1987), (glutamato-O,O')trimethyltin (Huber et al., 1989), [3-(2-thienyl)-2-propenoato)]triethyltin (Danish et al., 1995), 2-[(2,3-dimethylphenyl)aminobenzoato-O,O']trimethyltin (Tahir et al., 1997), (picolinato N-oxide)triphenyltin and (nicotinato N-oxide)triphenyltin (Ng & Kumar Das, 1995), triphenyl(3-ureidopropionato-O,O')tin (Lo et al., 1991) and (N-salicylidene-6-aminohexanoato-O,O')triphenyltin (Toong et al., 1992).

Experimental top

N-Maleoylglycine was prepared by the literature method (Rich et al., 1975). Solid maleamic acid (8.4 mmol) was suspended in dry toluene and treated with triethylamine (17.0 mmol). The mixture was refluxed under vigorous stirring for 4 h. The water formed was continuously removed via Dean–Stark apparatus. After cooling, toluene was removed from the orange layer, trimethyltin chloride (8.4 mmol) was added in toluene and the mixture was refluxed for 3–4 h. On cooling, triethylammonium chloride was filtered off, toluene removed using a rotary evaporator, and the mass left was crystallized from dichloromethane/n-hexane (1:1) solution to yield thin needles of the title compound.

Refinement top

Most H atoms were visible in difference maps, but were placed in idealized positions (0.95–0.99 Å) for refinement, which utilized a riding model. A torsional parameter was refined for each methyl group. The final difference map was essentially free of any chemically significant features, with the highest electron density 0.9 Å from the Sn atom. There are 51 Å3 voids in the structure at the inversion centres; the final difference map showed no significant electron density in those regions.

Computing details top

Data collection: MSC/AFC Diffractometer Control (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control; data reduction: TEXSAN (Molecular Structure Corporation, 1994); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN; software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) with the atomic numbering scheme. Displacement ellipsoids have been plotted at the 40% probability level and H-atoms assigned arbitrary radii. Symmetry codes: (i) 1 - x, 1/2 + y, 3/2 - z; (ii) 1 - x, -1/2 + y, 3/2 - z.
(N-Maleoylglycinate)trimethyltin(IV) top
Crystal data top
[Sn(CH3)3(C6H4NO4)]F(000) = 624
Mr = 317.89Dx = 1.633 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
a = 6.5848 (15) ÅCell parameters from 20 reflections
b = 9.991 (4) Åθ = 10.0–15.0°
c = 19.688 (6) ŵ = 1.97 mm1
β = 93.31 (3)°T = 170 K
V = 1293.1 (7) Å3Block, colourless
Z = 40.58 × 0.30 × 0.28 mm
Data collection top
Rigaku AFC-6S
diffractometer
2205 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 27.5°, θmin = 2.9°
ω–2θ scansh = 08
Absorption correction: empirical (using intensity measurements)
ψ scan (3 reflections) (North et al., 1968)
k = 012
Tmin = 0.373, Tmax = 0.576l = 2525
3235 measured reflections3 standard reflections every 200 reflections
2985 independent reflections intensity decay: <0.2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147 w = 1/[σ2(Fo2) + (0.0443P)2 + 11.0866P]
where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max < 0.001
2985 reflectionsΔρmax = 1.27 e Å3
140 parametersΔρmin = 1.38 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0006 (5)
Crystal data top
[Sn(CH3)3(C6H4NO4)]V = 1293.1 (7) Å3
Mr = 317.89Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.5848 (15) ŵ = 1.97 mm1
b = 9.991 (4) ÅT = 170 K
c = 19.688 (6) Å0.58 × 0.30 × 0.28 mm
β = 93.31 (3)°
Data collection top
Rigaku AFC-6S
diffractometer
2205 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
ψ scan (3 reflections) (North et al., 1968)
Rint = 0.054
Tmin = 0.373, Tmax = 0.5763 standard reflections every 200 reflections
3235 measured reflections intensity decay: <0.2%
2985 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.20 w = 1/[σ2(Fo2) + (0.0443P)2 + 11.0866P]
where P = (Fo2 + 2Fc2)/3
2985 reflectionsΔρmax = 1.27 e Å3
140 parametersΔρmin = 1.38 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.43129 (7)0.43723 (5)0.71962 (2)0.02729 (18)
O10.3498 (9)0.2800 (5)0.6442 (3)0.0349 (13)
O20.4945 (9)0.1244 (6)0.7103 (3)0.0390 (13)
O30.4406 (9)0.1879 (8)0.4785 (3)0.0539 (17)
O40.0976 (12)0.0980 (9)0.6040 (4)0.071 (2)
N10.2030 (11)0.1115 (7)0.5502 (3)0.0352 (15)
C10.2687 (15)0.5749 (9)0.6554 (5)0.045 (2)
H1A0.36370.62240.62740.068*
H1B0.19840.63950.68330.068*
H1C0.16880.52660.62590.068*
C20.7494 (14)0.4166 (11)0.7079 (7)0.061 (3)
H2A0.82150.41350.75280.092*
H2B0.79810.49310.68220.092*
H2C0.77490.33370.68310.092*
C30.2775 (13)0.3479 (9)0.7987 (4)0.0392 (19)
H3A0.37580.30210.82990.059*
H3B0.17850.28290.77950.059*
H3C0.20650.41700.82350.059*
C40.3995 (12)0.1603 (7)0.6567 (4)0.0300 (16)
C50.3382 (15)0.0570 (9)0.6037 (4)0.044 (2)
H5A0.46170.02150.58360.052*
H5B0.26980.01840.62570.052*
C60.2685 (12)0.1827 (9)0.4956 (4)0.0355 (17)
C70.0836 (13)0.2479 (10)0.4630 (5)0.046 (2)
H70.07910.29990.42260.055*
C80.0712 (13)0.2215 (11)0.4996 (5)0.049 (2)
H80.20680.25150.49000.058*
C90.0020 (14)0.1382 (10)0.5579 (5)0.043 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0307 (3)0.0246 (3)0.0259 (3)0.0004 (2)0.00420 (17)0.0013 (2)
O10.056 (4)0.029 (3)0.019 (3)0.005 (2)0.005 (2)0.000 (2)
O20.054 (4)0.031 (3)0.031 (3)0.008 (3)0.006 (3)0.003 (2)
O30.036 (3)0.078 (5)0.048 (4)0.005 (3)0.004 (3)0.004 (4)
O40.073 (5)0.074 (6)0.068 (5)0.013 (4)0.028 (4)0.016 (4)
N10.040 (4)0.034 (3)0.031 (3)0.002 (3)0.004 (3)0.003 (3)
C10.055 (5)0.030 (4)0.049 (5)0.005 (4)0.019 (4)0.008 (4)
C20.033 (5)0.062 (7)0.090 (8)0.003 (5)0.007 (5)0.000 (6)
C30.042 (5)0.034 (4)0.043 (5)0.005 (4)0.008 (4)0.002 (4)
C40.040 (4)0.025 (4)0.025 (4)0.006 (3)0.000 (3)0.001 (3)
C50.067 (6)0.028 (4)0.034 (4)0.009 (4)0.011 (4)0.003 (4)
C60.032 (4)0.044 (5)0.029 (4)0.002 (4)0.003 (3)0.008 (4)
C70.036 (5)0.061 (6)0.040 (5)0.008 (4)0.005 (4)0.011 (4)
C80.027 (4)0.068 (7)0.051 (5)0.005 (4)0.005 (4)0.001 (5)
C90.041 (5)0.045 (5)0.044 (5)0.007 (4)0.005 (4)0.006 (4)
Geometric parameters (Å, º) top
Sn1—C12.116 (8)O4—C91.203 (11)
Sn1—C22.131 (9)N1—C61.378 (11)
Sn1—C32.104 (8)N1—C91.393 (11)
Sn1—O12.207 (5)N1—C51.446 (10)
Sn1—O2i2.358 (6)C4—C51.507 (11)
O1—C41.260 (9)C6—C71.493 (11)
O2—C41.248 (9)C7—C81.308 (13)
O2—Sn1ii2.358 (6)C8—C91.468 (13)
O3—C61.202 (10)
C1—Sn1—C2117.7 (4)C9—N1—C5123.5 (8)
C1—Sn1—C3118.0 (4)O2—C4—O1123.4 (7)
C2—Sn1—C3123.9 (4)O2—C4—C5119.3 (7)
C1—Sn1—O188.0 (3)O1—C4—C5117.2 (7)
C2—Sn1—O193.4 (4)N1—C5—C4112.1 (7)
C3—Sn1—O195.0 (3)O3—C6—N1125.7 (8)
C1—Sn1—O2i85.1 (3)O3—C6—C7128.3 (9)
C2—Sn1—O2i88.2 (4)N1—C6—C7106.0 (7)
C3—Sn1—O2i89.8 (3)C8—C7—C6108.6 (8)
O1—Sn1—O2i172.90 (19)C7—C8—C9109.1 (8)
C4—O1—Sn1119.5 (5)O4—C9—N1124.8 (9)
C4—O2—Sn1ii143.1 (5)O4—C9—C8128.8 (9)
C6—N1—C9109.6 (7)N1—C9—C8106.4 (7)
C6—N1—C5123.7 (7)
C3—Sn1—O1—C457.9 (7)C5—N1—C6—O314.5 (14)
C1—Sn1—O1—C4175.8 (7)C9—N1—C6—C75.9 (9)
C2—Sn1—O1—C466.5 (7)C5—N1—C6—C7166.3 (8)
O2i—Sn1—O1—C4169.8 (16)O3—C6—C7—C8177.1 (10)
Sn1ii—O2—C4—O1159.5 (6)N1—C6—C7—C83.7 (11)
Sn1ii—O2—C4—C520.1 (14)C6—C7—C8—C90.1 (12)
Sn1—O1—C4—O20.2 (11)C6—N1—C9—O4174.5 (9)
Sn1—O1—C4—C5179.4 (6)C5—N1—C9—O414.0 (14)
C6—N1—C5—C482.1 (10)C6—N1—C9—C85.9 (10)
C9—N1—C5—C475.6 (11)C5—N1—C9—C8166.3 (8)
O2—C4—C5—N1170.9 (8)C7—C8—C9—O4176.9 (11)
O1—C4—C5—N18.7 (12)C7—C8—C9—N13.4 (11)
C9—N1—C6—O3174.9 (9)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Sn(CH3)3(C6H4NO4)]
Mr317.89
Crystal system, space groupMonoclinic, P21/c
Temperature (K)170
a, b, c (Å)6.5848 (15), 9.991 (4), 19.688 (6)
β (°) 93.31 (3)
V3)1293.1 (7)
Z4
Radiation typeMo Kα
µ (mm1)1.97
Crystal size (mm)0.58 × 0.30 × 0.28
Data collection
DiffractometerRigaku AFC-6S
diffractometer
Absorption correctionEmpirical (using intensity measurements)
ψ scan (3 reflections) (North et al., 1968)
Tmin, Tmax0.373, 0.576
No. of measured, independent and
observed [I > 2σ(I)] reflections
3235, 2985, 2205
Rint0.054
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.147, 1.20
No. of reflections2985
No. of parameters140
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0443P)2 + 11.0866P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.27, 1.38

Computer programs: MSC/AFC Diffractometer Control (Molecular Structure Corporation, 1988), MSC/AFC Diffractometer Control, TEXSAN (Molecular Structure Corporation, 1994), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), TEXSAN, SHELXL97.

Selected geometric parameters (Å, º) top
Sn1—C12.116 (8)O2—C41.248 (9)
Sn1—C22.131 (9)O3—C61.202 (10)
Sn1—C32.104 (8)O4—C91.203 (11)
Sn1—O12.207 (5)N1—C61.378 (11)
Sn1—O2i2.358 (6)N1—C91.393 (11)
O1—C41.260 (9)N1—C51.446 (10)
C1—Sn1—C2117.7 (4)C3—Sn1—O2i89.8 (3)
C1—Sn1—C3118.0 (4)O1—Sn1—O2i172.90 (19)
C2—Sn1—C3123.9 (4)C4—O1—Sn1119.5 (5)
C1—Sn1—O188.0 (3)C4—O2—Sn1ii143.1 (5)
C2—Sn1—O193.4 (4)C6—N1—C9109.6 (7)
C3—Sn1—O195.0 (3)C6—N1—C5123.7 (7)
C1—Sn1—O2i85.1 (3)C9—N1—C5123.5 (8)
C2—Sn1—O2i88.2 (4)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y1/2, z+3/2.
 

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