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The structure of the title compound, [Sn(CH3)3(C8H8NO4)], is composed of two independent monomers in the asymmetric unit, which form polymeric chains involving both O atoms of the acid moieties lying parallel to the b axis, and are separated by one half unit cell along the a axis. The geometry around the Sn atoms in both monomers is distorted trigonal-bipyramidal, where three methyl C atoms occupy the equatorial positions with almost identical Sn-C distances, and O atoms from two symmetry-related ligands are in the axial positions with significantly different Sn-O distances.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007974/ac6093sup1.cif
Contains datablocks Global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007974/ac6093Isup2.hkl
Contains datablock I

CCDC reference: 239048

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.039
  • wR factor = 0.081
  • Data-to-parameter ratio = 20.6

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT432_ALERT_2_C Short Inter X...Y Contact O8 .. C10 .. 2.97 Ang.
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C11 H17 N1 O4 Sn1 Atom count from _chemical_formula_moiety:
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Trimethyltin(IV)2-(N-maleoyl)-2-methylpropionate top
Crystal data top
[Sn(C8H8NO4)(CH3)3]F(000) = 1376
Mr = 345.95Dx = 1.660 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11788 reflections
a = 21.738 (5) Åθ = 3.4–27.5°
b = 9.700 (2) ŵ = 1.85 mm1
c = 13.447 (3) ÅT = 173 K
β = 102.442 (13)°Block, colorless
V = 2768.8 (11) Å30.18 × 0.15 × 0.15 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
6332 independent reflections
Radiation source: fine-focus sealed tube4188 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω and φ scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 2828
Tmin = 0.725, Tmax = 0.761k = 1212
11788 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.026P)2]
where P = (Fo2 + 2Fc2)/3
6332 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.85 e Å3
0 restraintsΔρmin = 0.81 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.477587 (11)1.09138 (3)0.20148 (2)0.02330 (9)
O10.40017 (11)0.9629 (3)0.1353 (2)0.0267 (7)
O20.44006 (11)0.7749 (3)0.2216 (2)0.0327 (7)
O30.31989 (13)0.9251 (3)0.2794 (2)0.0391 (8)
O40.20732 (13)0.7736 (3)0.0259 (3)0.0581 (10)
N10.28187 (14)0.8425 (3)0.1165 (3)0.0270 (8)
C10.46890 (18)1.0801 (4)0.3552 (3)0.0293 (10)
H1A0.51001.05890.39890.044*
H1B0.43881.00750.36230.044*
H1C0.45381.16880.37560.044*
C20.54781 (17)0.9871 (4)0.1436 (3)0.0344 (11)
H2A0.52780.92910.08600.052*
H2B0.57280.92930.19710.052*
H2C0.57531.05470.12080.052*
C30.43501 (17)1.2571 (4)0.1090 (3)0.0347 (11)
H3A0.41781.22340.03990.052*
H3B0.46661.32840.10670.052*
H3C0.40101.29600.13760.052*
C40.39788 (17)0.8360 (4)0.1629 (3)0.0247 (9)
C50.33779 (17)0.7603 (4)0.1066 (3)0.0280 (10)
C60.33220 (19)0.6169 (4)0.1509 (4)0.0482 (14)
H6A0.32780.62560.22160.072*
H6B0.37010.56330.14870.072*
H6C0.29510.57000.11080.072*
C70.3432 (2)0.7531 (5)0.0049 (3)0.0512 (14)
H7A0.33860.84580.03450.077*
H7B0.30990.69330.04280.077*
H7C0.38450.71550.00880.077*
C80.27819 (18)0.9166 (4)0.2049 (3)0.0305 (10)
C90.21281 (18)0.9710 (4)0.1881 (4)0.0376 (11)
H90.19691.02880.23370.045*
C100.18064 (19)0.9258 (4)0.0997 (4)0.0394 (12)
H100.13780.94650.07110.047*
C110.2216 (2)0.8384 (5)0.0524 (4)0.0378 (12)
Sn20.030662 (11)0.08059 (3)0.27622 (2)0.02180 (9)
O50.10630 (11)0.2101 (3)0.2496 (2)0.0275 (7)
O60.04816 (11)0.3988 (2)0.2055 (2)0.0268 (7)
O70.28836 (12)0.2866 (3)0.1911 (2)0.0393 (8)
O80.16758 (12)0.3893 (3)0.4203 (2)0.0379 (8)
N20.21347 (13)0.3533 (3)0.2827 (2)0.0221 (7)
C120.00419 (17)0.1993 (4)0.3936 (3)0.0277 (10)
H12A0.03950.25810.42600.042*
H12B0.00690.13730.44460.042*
H12C0.03220.25700.36420.042*
C130.09606 (17)0.0753 (4)0.3378 (3)0.0338 (11)
H13A0.13610.03270.37110.051*
H13B0.10290.13600.28290.051*
H13C0.07940.12920.38770.051*
C140.01900 (18)0.0834 (4)0.1226 (3)0.0305 (10)
H14A0.04100.17170.10780.046*
H14B0.04980.00800.11100.046*
H14C0.01070.07170.07780.046*
C150.09923 (17)0.3367 (4)0.2247 (3)0.0212 (9)
C160.15965 (16)0.4097 (4)0.2076 (3)0.0214 (9)
C170.15709 (17)0.5653 (4)0.2204 (3)0.0316 (10)
H17A0.19760.60570.21510.047*
H17B0.14850.58680.28730.047*
H17C0.12350.60360.16700.047*
C180.16304 (17)0.3731 (4)0.0976 (3)0.0300 (10)
H18A0.16810.27320.09180.045*
H18B0.19910.42030.07980.045*
H18C0.12410.40260.05100.045*
C190.27049 (17)0.2961 (4)0.2692 (3)0.0281 (10)
C200.30426 (19)0.2533 (5)0.3726 (3)0.0420 (12)
H200.34430.20950.38780.050*
C210.27103 (18)0.2844 (5)0.4397 (3)0.0410 (12)
H210.28300.26830.51090.049*
C220.21117 (19)0.3495 (4)0.3854 (3)0.0302 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02313 (15)0.02085 (16)0.02611 (18)0.00095 (12)0.00574 (12)0.00049 (13)
O10.0269 (14)0.0233 (15)0.0279 (17)0.0063 (12)0.0017 (12)0.0011 (13)
O20.0240 (14)0.0279 (16)0.043 (2)0.0037 (13)0.0002 (13)0.0005 (14)
O30.0357 (16)0.057 (2)0.0230 (18)0.0037 (16)0.0040 (14)0.0005 (16)
O40.0416 (19)0.065 (2)0.056 (3)0.0039 (18)0.0152 (17)0.022 (2)
N10.0197 (16)0.0294 (19)0.030 (2)0.0026 (15)0.0024 (15)0.0010 (17)
C10.035 (2)0.028 (2)0.027 (2)0.000 (2)0.0106 (19)0.002 (2)
C20.032 (2)0.034 (3)0.041 (3)0.001 (2)0.014 (2)0.003 (2)
C30.036 (2)0.029 (2)0.036 (3)0.000 (2)0.001 (2)0.003 (2)
C40.025 (2)0.020 (2)0.031 (3)0.0030 (19)0.0102 (19)0.0071 (19)
C50.025 (2)0.026 (2)0.033 (3)0.0051 (19)0.0040 (18)0.003 (2)
C60.031 (2)0.024 (2)0.085 (4)0.005 (2)0.002 (3)0.003 (2)
C70.047 (3)0.064 (3)0.044 (3)0.006 (3)0.012 (2)0.025 (3)
C80.032 (2)0.029 (2)0.034 (3)0.001 (2)0.013 (2)0.007 (2)
C90.032 (2)0.035 (3)0.051 (3)0.005 (2)0.019 (2)0.009 (2)
C100.027 (2)0.039 (3)0.051 (3)0.005 (2)0.006 (2)0.010 (3)
C110.038 (3)0.033 (3)0.038 (3)0.010 (2)0.002 (2)0.008 (2)
Sn20.02237 (14)0.01878 (15)0.02483 (17)0.00005 (12)0.00639 (12)0.00005 (12)
O50.0239 (14)0.0179 (15)0.0431 (19)0.0002 (12)0.0125 (13)0.0054 (13)
O60.0244 (14)0.0238 (16)0.0333 (18)0.0010 (13)0.0088 (12)0.0001 (13)
O70.0306 (15)0.059 (2)0.0315 (19)0.0086 (15)0.0131 (14)0.0022 (16)
O80.0377 (16)0.051 (2)0.0276 (18)0.0110 (15)0.0128 (14)0.0049 (15)
N20.0203 (16)0.0252 (18)0.021 (2)0.0020 (15)0.0040 (14)0.0014 (15)
C120.035 (2)0.021 (2)0.028 (3)0.0046 (19)0.0093 (19)0.0053 (18)
C130.028 (2)0.029 (2)0.043 (3)0.001 (2)0.004 (2)0.007 (2)
C140.037 (2)0.032 (2)0.021 (2)0.006 (2)0.0042 (19)0.003 (2)
C150.022 (2)0.023 (2)0.019 (2)0.0024 (18)0.0053 (17)0.0041 (18)
C160.0206 (19)0.022 (2)0.021 (2)0.0015 (18)0.0037 (16)0.0036 (18)
C170.028 (2)0.022 (2)0.045 (3)0.0033 (19)0.008 (2)0.004 (2)
C180.023 (2)0.043 (3)0.025 (3)0.0008 (19)0.0065 (18)0.006 (2)
C190.0208 (19)0.035 (3)0.030 (3)0.0003 (19)0.0084 (18)0.001 (2)
C200.026 (2)0.060 (3)0.037 (3)0.009 (2)0.000 (2)0.008 (3)
C210.032 (2)0.064 (3)0.023 (3)0.008 (2)0.002 (2)0.006 (2)
C220.030 (2)0.033 (2)0.029 (3)0.001 (2)0.009 (2)0.001 (2)
Geometric parameters (Å, º) top
Sn1—C22.114 (4)Sn2—C142.115 (4)
Sn1—C32.119 (4)Sn2—C132.118 (4)
Sn1—C12.119 (4)Sn2—C122.131 (4)
Sn1—O12.129 (2)Sn2—O52.159 (2)
Sn1—O2i2.578 (3)Sn2—O6iii2.508 (3)
O1—C41.290 (4)O5—C151.273 (4)
O2—C41.226 (4)O6—C151.240 (4)
O2—Sn1ii2.578 (3)O6—Sn2iv2.508 (3)
O3—C81.201 (4)O7—C191.199 (5)
O4—C111.208 (5)O8—C221.208 (5)
N1—C81.405 (5)N2—C221.394 (5)
N1—C111.405 (5)N2—C191.405 (5)
N1—C51.483 (5)N2—C161.476 (4)
C1—H1A0.9800C12—H12A0.9800
C1—H1B0.9800C12—H12B0.9800
C1—H1C0.9800C12—H12C0.9800
C2—H2A0.9800C13—H13A0.9800
C2—H2B0.9800C13—H13B0.9800
C2—H2C0.9800C13—H13C0.9800
C3—H3A0.9800C14—H14A0.9800
C3—H3B0.9800C14—H14B0.9800
C3—H3C0.9800C14—H14C0.9800
C4—C51.547 (5)C15—C161.552 (5)
C5—C61.528 (5)C16—C171.522 (5)
C5—C71.530 (6)C16—C181.539 (5)
C6—H6A0.9800C17—H17A0.9800
C6—H6B0.9800C17—H17B0.9800
C6—H6C0.9800C17—H17C0.9800
C7—H7A0.9800C18—H18A0.9800
C7—H7B0.9800C18—H18B0.9800
C7—H7C0.9800C18—H18C0.9800
C8—C91.487 (5)C19—C201.485 (5)
C9—C101.318 (6)C20—C211.307 (6)
C9—H90.9500C20—H200.9500
C10—C111.470 (6)C21—C221.488 (5)
C10—H100.9500C21—H210.9500
C2—Sn1—C3113.90 (17)C14—Sn2—C13123.32 (16)
C2—Sn1—C1123.91 (16)C14—Sn2—C12123.65 (15)
C3—Sn1—C1119.48 (16)C13—Sn2—C12111.22 (17)
C2—Sn1—O197.74 (13)C14—Sn2—O594.44 (13)
C3—Sn1—O189.59 (12)C13—Sn2—O590.53 (13)
C1—Sn1—O198.56 (13)C12—Sn2—O598.34 (12)
C2—Sn1—O2i89.08 (13)C14—Sn2—O6iii83.62 (12)
C3—Sn1—O2i83.66 (12)C13—Sn2—O6iii82.81 (12)
C1—Sn1—O2i81.03 (12)C12—Sn2—O6iii90.47 (12)
O1—Sn1—O2i171.92 (9)O5—Sn2—O6iii170.46 (9)
C4—O1—Sn1121.0 (2)C15—O5—Sn2123.5 (2)
C4—O2—Sn1ii161.9 (3)C15—O6—Sn2iv157.1 (2)
C8—N1—C11108.5 (3)C22—N2—C19109.8 (3)
C8—N1—C5123.2 (3)C22—N2—C16119.7 (3)
C11—N1—C5127.1 (4)C19—N2—C16130.5 (3)
Sn1—C1—H1A109.5Sn2—C12—H12A109.5
Sn1—C1—H1B109.5Sn2—C12—H12B109.5
H1A—C1—H1B109.5H12A—C12—H12B109.5
Sn1—C1—H1C109.5Sn2—C12—H12C109.5
H1A—C1—H1C109.5H12A—C12—H12C109.5
H1B—C1—H1C109.5H12B—C12—H12C109.5
Sn1—C2—H2A109.5Sn2—C13—H13A109.5
Sn1—C2—H2B109.5Sn2—C13—H13B109.5
H2A—C2—H2B109.5H13A—C13—H13B109.5
Sn1—C2—H2C109.5Sn2—C13—H13C109.5
H2A—C2—H2C109.5H13A—C13—H13C109.5
H2B—C2—H2C109.5H13B—C13—H13C109.5
Sn1—C3—H3A109.5Sn2—C14—H14A109.5
Sn1—C3—H3B109.5Sn2—C14—H14B109.5
H3A—C3—H3B109.5H14A—C14—H14B109.5
Sn1—C3—H3C109.5Sn2—C14—H14C109.5
H3A—C3—H3C109.5H14A—C14—H14C109.5
H3B—C3—H3C109.5H14B—C14—H14C109.5
O2—C4—O1125.2 (3)O6—C15—O5125.1 (3)
O2—C4—C5121.4 (3)O6—C15—C16119.7 (3)
O1—C4—C5113.1 (3)O5—C15—C16114.9 (3)
N1—C5—C6108.6 (3)N2—C16—C17109.5 (3)
N1—C5—C7110.5 (3)N2—C16—C18112.2 (3)
C6—C5—C7111.7 (4)C17—C16—C18110.3 (3)
N1—C5—C4108.8 (3)N2—C16—C15107.5 (3)
C6—C5—C4111.7 (3)C17—C16—C15112.5 (3)
C7—C5—C4105.5 (3)C18—C16—C15104.8 (3)
C5—C6—H6A109.5C16—C17—H17A109.5
C5—C6—H6B109.5C16—C17—H17B109.5
H6A—C6—H6B109.5H17A—C17—H17B109.5
C5—C6—H6C109.5C16—C17—H17C109.5
H6A—C6—H6C109.5H17A—C17—H17C109.5
H6B—C6—H6C109.5H17B—C17—H17C109.5
C5—C7—H7A109.5C16—C18—H18A109.5
C5—C7—H7B109.5C16—C18—H18B109.5
H7A—C7—H7B109.5H18A—C18—H18B109.5
C5—C7—H7C109.5C16—C18—H18C109.5
H7A—C7—H7C109.5H18A—C18—H18C109.5
H7B—C7—H7C109.5H18B—C18—H18C109.5
O3—C8—N1124.8 (4)O7—C19—N2127.2 (4)
O3—C8—C9128.8 (4)O7—C19—C20127.6 (4)
N1—C8—C9106.3 (3)N2—C19—C20105.2 (4)
C10—C9—C8108.8 (4)C21—C20—C19110.3 (4)
C10—C9—H9125.6C21—C20—H20124.9
C8—C9—H9125.6C19—C20—H20124.9
C9—C10—C11109.2 (4)C20—C21—C22108.4 (4)
C9—C10—H10125.4C20—C21—H21125.8
C11—C10—H10125.4C22—C21—H21125.8
O4—C11—N1125.5 (4)O8—C22—N2125.1 (4)
O4—C11—C10127.7 (4)O8—C22—C21128.4 (4)
N1—C11—C10106.8 (4)N2—C22—C21106.4 (4)
C2—Sn1—O1—C466.1 (3)C14—Sn2—O5—C1567.4 (3)
C3—Sn1—O1—C4179.8 (3)C13—Sn2—O5—C15169.1 (3)
C1—Sn1—O1—C460.0 (3)C12—Sn2—O5—C1557.6 (3)
Sn1ii—O2—C4—O1129.0 (7)Sn2iv—O6—C15—O5122.1 (6)
Sn1ii—O2—C4—C545.2 (11)Sn2iv—O6—C15—C1664.6 (8)
Sn1—O1—C4—O25.7 (5)Sn2—O5—C15—O65.4 (6)
Sn1—O1—C4—C5179.7 (2)Sn2—O5—C15—C16179.0 (2)
C8—N1—C5—C685.5 (5)C22—N2—C16—C1771.4 (4)
C11—N1—C5—C680.9 (5)C19—N2—C16—C17109.9 (4)
C8—N1—C5—C7151.7 (4)C22—N2—C16—C18165.8 (3)
C11—N1—C5—C741.9 (5)C19—N2—C16—C1812.9 (5)
C8—N1—C5—C436.3 (5)C22—N2—C16—C1551.1 (4)
C11—N1—C5—C4157.3 (4)C19—N2—C16—C15127.6 (4)
O2—C4—C5—N1132.7 (4)O6—C15—C16—N2149.7 (3)
O1—C4—C5—N152.5 (5)O5—C15—C16—N236.3 (4)
O2—C4—C5—C612.8 (6)O6—C15—C16—C1729.1 (5)
O1—C4—C5—C6172.3 (4)O5—C15—C16—C17156.9 (3)
O2—C4—C5—C7108.7 (4)O6—C15—C16—C1890.8 (4)
O1—C4—C5—C766.1 (4)O5—C15—C16—C1883.2 (4)
C11—N1—C8—O3171.1 (4)C22—N2—C19—O7177.9 (4)
C5—N1—C8—O32.5 (6)C16—N2—C19—O73.3 (7)
C11—N1—C8—C95.3 (4)C22—N2—C19—C200.8 (4)
C5—N1—C8—C9173.9 (3)C16—N2—C19—C20177.9 (3)
O3—C8—C9—C10173.2 (4)O7—C19—C20—C21177.6 (5)
N1—C8—C9—C103.0 (5)N2—C19—C20—C211.1 (5)
C8—C9—C10—C110.5 (5)C19—C20—C21—C220.9 (5)
C8—N1—C11—O4173.8 (4)C19—N2—C22—O8178.8 (4)
C5—N1—C11—O45.7 (7)C16—N2—C22—O80.2 (6)
C8—N1—C11—C105.6 (5)C19—N2—C22—C210.4 (4)
C5—N1—C11—C10173.7 (4)C16—N2—C22—C21178.6 (3)
C9—C10—C11—O4175.6 (5)C20—C21—C22—O8178.0 (5)
C9—C10—C11—N13.8 (5)C20—C21—C22—N20.3 (5)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x, y1/2, z+1/2; (iv) x, y+1/2, z+1/2.
 

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