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In the title complex, [Sn2(CH3)4(C10H8N2O3)2(CH4O)2], the SnIV ion has a distorted penta­gonal–bipyramidal coordination geometry. The carboxyl­ate O atom bridges two SnIV ions to form the dimeric complex, which is located on an inversion center. Hydrogen bonding between the methanol and carboxylate groups helps to stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005570/xu2188sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005570/xu2188Isup2.hkl
Contains datablock I

CCDC reference: 654719

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.034
  • wR factor = 0.084
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT413_ALERT_2_B Short Inter XH3 .. XHn H11C .. H12B .. 1.98 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O1 .. 2.83 Ang.
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.75 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1 PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

[µ-Pyruvic acid benzoylhydrazonato(2-)]bis[methanoldimethyltin(IV)] top
Crystal data top
[Sn2(CH3)4(C10H8N2O3)2(CH4O)2]F(000) = 768
Mr = 769.96Dx = 1.613 Mg m3
Monoclinic, P21/cMelting point: 396.5 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.408 (10) ÅCell parameters from 2118 reflections
b = 18.910 (17) Åθ = 2.3–22.7°
c = 8.911 (8) ŵ = 1.63 mm1
β = 115.346 (15)°T = 298 K
V = 1585 (3) Å3Block, colorless
Z = 20.47 × 0.42 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2809 independent reflections
Radiation source: fine-focus sealed tube2060 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1210
Tmin = 0.470, Tmax = 0.750k = 1422
8215 measured reflectionsl = 1010
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0338P)2 + 2.1392P]
where P = (Fo2 + 2Fc2)/3
2809 reflections(Δ/σ)max = 0.004
187 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.55 e Å3
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
xyzUiso*/Ueq
O40.0318 (6)0.3280 (2)0.8067 (6)0.0984 (18)
Sn10.08931 (4)0.441322 (17)0.86637 (4)0.04350 (13)
O10.1036 (3)0.54808 (16)0.9990 (4)0.0457 (8)
O20.2157 (4)0.65220 (18)1.0643 (4)0.0586 (10)
O30.1890 (4)0.38612 (17)0.7284 (4)0.0550 (9)
N10.2599 (4)0.5095 (2)0.8459 (4)0.0418 (9)
N20.3359 (4)0.4833 (2)0.7623 (5)0.0474 (10)
C10.2890 (5)0.4193 (3)0.7066 (6)0.0425 (11)
C20.3584 (5)0.3819 (3)0.6126 (5)0.0446 (12)
C30.4727 (6)0.4115 (3)0.5933 (6)0.0576 (14)
H30.50700.45570.63820.069*
C40.5362 (6)0.3750 (3)0.5067 (7)0.0688 (16)
H40.61280.39490.49440.083*
C50.4856 (6)0.3095 (3)0.4394 (7)0.0621 (15)
H50.52810.28510.38200.074*
C60.3723 (6)0.2804 (3)0.4577 (7)0.0606 (15)
H60.33820.23620.41230.073*
C70.3078 (6)0.3165 (3)0.5436 (6)0.0564 (14)
H70.23070.29650.55460.068*
C80.2874 (5)0.5716 (3)0.9106 (6)0.0443 (12)
C90.3950 (6)0.6209 (3)0.9012 (7)0.0630 (15)
H9A0.44510.59800.84600.094*
H9B0.46110.63421.01140.094*
H9C0.34830.66240.84020.094*
C100.1962 (5)0.5933 (3)0.9985 (6)0.0426 (11)
C110.2105 (6)0.3931 (3)1.0956 (6)0.0618 (15)
H11A0.30910.39431.11750.093*
H11B0.18060.34491.09260.093*
H11C0.19720.41811.18170.093*
C120.0846 (6)0.4802 (4)0.6581 (6)0.0689 (16)
H12A0.05180.50080.58230.103*
H12B0.13280.51540.69230.103*
H12C0.14880.44210.60410.103*
C130.0620 (8)0.2781 (4)0.6860 (10)0.117 (3)
H13A0.04100.29660.59860.175*
H13B0.16090.26600.64200.175*
H13C0.00540.23680.73220.175*
H140.107 (7)0.330 (4)0.836 (9)0.12 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.122 (4)0.080 (3)0.144 (4)0.051 (3)0.106 (4)0.060 (3)
Sn10.0501 (2)0.0403 (2)0.0479 (2)0.00086 (16)0.02833 (17)0.00150 (16)
O10.049 (2)0.0431 (19)0.055 (2)0.0059 (15)0.0319 (17)0.0056 (15)
O20.074 (3)0.046 (2)0.071 (2)0.0093 (18)0.046 (2)0.0124 (18)
O30.068 (2)0.045 (2)0.072 (2)0.0072 (17)0.049 (2)0.0094 (17)
N10.045 (2)0.042 (2)0.043 (2)0.0033 (18)0.0243 (19)0.0011 (18)
N20.052 (3)0.050 (3)0.050 (2)0.001 (2)0.031 (2)0.003 (2)
C10.046 (3)0.046 (3)0.042 (3)0.003 (2)0.025 (2)0.002 (2)
C20.049 (3)0.049 (3)0.038 (3)0.007 (2)0.020 (2)0.003 (2)
C30.058 (3)0.068 (4)0.059 (3)0.007 (3)0.036 (3)0.012 (3)
C40.057 (4)0.093 (5)0.074 (4)0.001 (3)0.044 (3)0.008 (3)
C50.069 (4)0.066 (4)0.065 (4)0.014 (3)0.042 (3)0.003 (3)
C60.087 (4)0.044 (3)0.065 (4)0.010 (3)0.047 (3)0.003 (3)
C70.076 (4)0.044 (3)0.065 (3)0.004 (3)0.045 (3)0.003 (3)
C80.046 (3)0.049 (3)0.041 (3)0.001 (2)0.022 (2)0.000 (2)
C90.067 (4)0.055 (3)0.083 (4)0.011 (3)0.047 (3)0.010 (3)
C100.052 (3)0.037 (3)0.043 (3)0.002 (2)0.024 (2)0.005 (2)
C110.068 (4)0.062 (4)0.062 (3)0.019 (3)0.034 (3)0.016 (3)
C120.060 (4)0.096 (5)0.051 (3)0.003 (3)0.024 (3)0.005 (3)
C130.117 (6)0.107 (6)0.164 (8)0.045 (5)0.096 (6)0.082 (6)
Geometric parameters (Å, º) top
Sn1—O12.312 (3)C4—H40.9300
Sn1—O1i2.751 (4)C5—C61.373 (7)
Sn1—O32.184 (3)C5—H50.9300
Sn1—O42.427 (4)C6—C71.393 (7)
Sn1—N12.263 (4)C6—H60.9300
Sn1—C112.094 (5)C7—H70.9300
Sn1—C122.094 (5)C8—C91.487 (7)
O4—C131.362 (7)C8—C101.523 (6)
O4—H140.93 (7)C9—H9A0.9600
O1—C101.291 (5)C9—H9B0.9600
O2—C101.234 (5)C9—H9C0.9600
O3—C11.300 (5)C11—H11A0.9600
N1—C81.286 (6)C11—H11B0.9600
N1—N21.390 (5)C11—H11C0.9600
N2—C11.318 (6)C12—H12A0.9600
C1—C21.497 (6)C12—H12B0.9600
C2—C71.382 (7)C12—H12C0.9600
C2—C31.391 (7)C13—H13A0.9600
C3—C41.394 (7)C13—H13B0.9600
C3—H30.9300C13—H13C0.9600
C4—C51.379 (8)
C13—O4—Sn1135.0 (4)C3—C4—H4119.9
C13—O4—H14109 (4)C6—C5—C4119.7 (5)
Sn1—O4—H14109 (4)C6—C5—H5120.1
C11—Sn1—C12161.5 (2)C4—C5—H5120.1
C11—Sn1—O396.22 (19)C5—C6—C7120.6 (5)
C12—Sn1—O396.15 (19)C5—C6—H6119.7
C11—Sn1—N199.24 (19)C7—C6—H6119.7
C12—Sn1—N198.0 (2)C2—C7—C6120.1 (5)
O3—Sn1—N169.44 (14)C2—C7—H7119.9
C11—Sn1—O190.07 (18)C6—C7—H7119.9
C12—Sn1—O189.4 (2)N1—C8—C9125.2 (4)
O3—Sn1—O1139.76 (12)N1—C8—C10114.1 (4)
N1—Sn1—O170.31 (13)C9—C8—C10120.7 (4)
C11—Sn1—O482.5 (2)C8—C9—H9A109.5
C12—Sn1—O486.8 (2)C8—C9—H9B109.5
O3—Sn1—O477.39 (14)H9A—C9—H9B109.5
N1—Sn1—O4146.79 (14)C8—C9—H9C109.5
O1—Sn1—O4142.83 (13)H9A—C9—H9C109.5
C11—Sn1—O1i81.59 (17)H9B—C9—H9C109.5
C12—Sn1—O1i81.13 (18)O2—C10—O1124.6 (4)
O3—Sn1—O1i153.03 (11)O2—C10—C8118.4 (4)
N1—Sn1—O1i137.52 (12)O1—C10—C8117.0 (4)
O1—Sn1—O1i67.21 (12)Sn1—C11—H11A109.5
O4—Sn1—O1i75.68 (13)Sn1—C11—H11B109.5
C10—O1—Sn1117.5 (3)H11A—C11—H11B109.5
C1—O3—Sn1117.2 (3)Sn1—C11—H11C109.5
C8—N1—N2119.8 (4)H11A—C11—H11C109.5
C8—N1—Sn1121.1 (3)H11B—C11—H11C109.5
N2—N1—Sn1119.1 (3)Sn1—C12—H12A109.5
C1—N2—N1108.9 (4)Sn1—C12—H12B109.5
O3—C1—N2125.3 (4)H12A—C12—H12B109.5
O3—C1—C2117.6 (4)Sn1—C12—H12C109.5
N2—C1—C2117.0 (4)H12A—C12—H12C109.5
C7—C2—C3119.2 (5)H12B—C12—H12C109.5
C7—C2—C1119.3 (4)O4—C13—H13A109.5
C3—C2—C1121.5 (5)O4—C13—H13B109.5
C2—C3—C4120.1 (5)H13A—C13—H13B109.5
C2—C3—H3119.9O4—C13—H13C109.5
C4—C3—H3119.9H13A—C13—H13C109.5
C5—C4—C3120.2 (5)H13B—C13—H13C109.5
C5—C4—H4119.9
C1—N2—N1—C8179.7 (4)
Symmetry code: (i) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H14···O2i0.93 (7)1.74 (7)2.648 (6)165 (6)
Symmetry code: (i) x, y+1, z+2.
 

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