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The title compound, [Sn2Cl2(CH3)4(C6H5N2O2)2], forms infinite one-dimensional zigzag chains that propagate in a helical fashion along the c axis via an Sn—O=C—O—Sn—O bridge which involves the carboxyl­ate groups of two methyl­pyrazine­carboxyl­ate ligands. These display both chelating and bridging coordination behaviour. The asymmetric unit contains two Sn atoms; one adopts a distorted trigonal–bipyramidal geometry, while the other is in a distorted penta­gonal–bipyramidal configuration.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007866/sj2225sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007866/sj2225Isup2.hkl
Contains datablock I

CCDC reference: 641508

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.013 Å
  • R factor = 0.045
  • wR factor = 0.115
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

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Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn2 PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 13 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C6 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C12
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 4154 Count of symmetry unique reflns 2260 Completeness (_total/calc) 183.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1894 Fraction of Friedel pairs measured 0.838 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

catena-Poly[[dichloridodimethyltin(IV)]-µ-5-methylpyrazine-2-carboxylato- κ3O:O',N-[dimethyltin(IV)]]-µ-5-methylpyrazine-2-carboxylato-κ3O,N:O'] top
Crystal data top
[Sn2Cl2(CH3)4(C6H5N2O2)2]F(000) = 1248
Mr = 642.66Dx = 1.811 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 5188 reflections
a = 30.205 (7) Åθ = 2.3–26.6°
b = 10.824 (3) ŵ = 2.37 mm1
c = 7.2092 (16) ÅT = 298 K
V = 2357.0 (9) Å3Block, colourless
Z = 40.58 × 0.43 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4154 independent reflections
Radiation source: fine-focus sealed tube3672 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2935
Tmin = 0.340, Tmax = 0.780k = 1210
11833 measured reflectionsl = 88
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.064P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4154 reflectionsΔρmax = 0.66 e Å3
253 parametersΔρmin = 1.22 e Å3
1 restraintAbsolute structure: Flack (1983), with 2258 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (5)
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
Sn10.068129 (15)0.40365 (5)0.43334 (10)0.03839 (16)
Sn20.195366 (18)0.01532 (5)0.37802 (8)0.04193 (17)
Cl10.20221 (9)0.2417 (2)0.4229 (4)0.0702 (7)
Cl20.12116 (8)0.0334 (3)0.2649 (5)0.0754 (8)
N10.1311 (2)0.4720 (6)0.2362 (10)0.0391 (16)
N20.2063 (3)0.5093 (7)0.0226 (15)0.061 (2)
N30.0425 (2)0.2323 (6)0.6386 (9)0.0420 (16)
N40.0048 (2)0.0550 (7)0.8664 (11)0.0543 (18)
O10.12529 (17)0.2653 (5)0.4449 (10)0.0532 (14)
O20.1886 (2)0.1961 (6)0.3241 (11)0.068 (2)
O30.0000 (2)0.4444 (6)0.5715 (9)0.0550 (16)
O40.0456 (2)0.4092 (6)0.8111 (9)0.0529 (16)
C10.1587 (3)0.2750 (8)0.3446 (11)0.047 (2)
C20.1633 (3)0.3883 (8)0.2277 (13)0.046 (2)
C30.2005 (3)0.4068 (9)0.1215 (16)0.061 (3)
H30.22230.34600.11880.073*
C40.1742 (3)0.5941 (8)0.0309 (12)0.046 (2)
C50.1371 (3)0.5743 (7)0.1372 (12)0.043 (2)
H50.11530.63490.14010.052*
C60.1800 (3)0.7118 (8)0.0750 (16)0.060 (2)
H6A0.20750.70940.14170.091*
H6B0.18020.78020.00970.091*
H6C0.15590.72130.16110.091*
C70.0152 (3)0.3803 (8)0.7020 (12)0.0413 (19)
C80.0052 (3)0.2553 (8)0.7297 (12)0.0406 (18)
C90.0133 (3)0.1647 (8)0.8407 (11)0.049 (2)
H90.03990.18190.90020.059*
C100.0425 (3)0.0327 (8)0.7802 (12)0.044 (2)
C110.0612 (3)0.1214 (8)0.6617 (13)0.0416 (19)
H110.08720.10270.59800.050*
C120.0652 (3)0.0870 (8)0.8115 (18)0.061 (3)
H12A0.04800.13660.89520.091*
H12B0.09390.07240.86410.091*
H12C0.06840.12960.69550.091*
C130.0424 (3)0.3023 (9)0.2097 (13)0.055 (2)
H13A0.04820.21600.22840.083*
H13B0.05620.32900.09670.083*
H13C0.01100.31550.20190.083*
C140.0970 (3)0.5022 (9)0.6523 (14)0.055 (2)
H14A0.10800.44530.74330.082*
H14B0.07520.55490.70810.082*
H14C0.12100.55150.60570.082*
C150.2364 (4)0.0078 (10)0.1454 (14)0.058 (3)
H15A0.26610.01120.18350.087*
H15B0.22600.05510.06240.087*
H15C0.23610.08630.08340.087*
C160.1902 (3)0.0295 (10)0.6630 (14)0.056 (2)
H16A0.18710.11730.67660.084*
H16B0.21640.00260.72670.084*
H16C0.16480.01100.71510.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0330 (3)0.0427 (3)0.0395 (3)0.0024 (2)0.0018 (3)0.0018 (2)
Sn20.0450 (3)0.0446 (3)0.0362 (3)0.0004 (2)0.0025 (2)0.0085 (3)
Cl10.1055 (18)0.0438 (11)0.0615 (16)0.0078 (11)0.0235 (17)0.0117 (11)
Cl20.0459 (14)0.099 (2)0.081 (2)0.0080 (14)0.0144 (13)0.0091 (16)
N10.031 (3)0.042 (4)0.044 (4)0.000 (3)0.000 (3)0.013 (3)
N20.060 (5)0.054 (5)0.069 (6)0.002 (4)0.026 (5)0.013 (4)
N30.037 (4)0.050 (4)0.039 (4)0.003 (3)0.002 (3)0.000 (3)
N40.049 (4)0.059 (4)0.055 (4)0.010 (3)0.014 (4)0.004 (4)
O10.045 (3)0.051 (3)0.064 (3)0.014 (2)0.013 (3)0.025 (3)
O20.061 (4)0.043 (3)0.101 (7)0.018 (3)0.029 (4)0.022 (4)
O30.046 (4)0.057 (4)0.062 (4)0.014 (3)0.017 (3)0.009 (3)
O40.046 (4)0.054 (4)0.058 (4)0.004 (3)0.011 (3)0.008 (3)
C10.049 (5)0.047 (4)0.045 (5)0.007 (4)0.013 (4)0.012 (4)
C20.046 (5)0.040 (5)0.050 (5)0.010 (4)0.002 (4)0.006 (4)
C30.054 (6)0.053 (6)0.075 (7)0.006 (4)0.032 (5)0.027 (5)
C40.058 (6)0.049 (5)0.031 (4)0.012 (4)0.003 (4)0.001 (3)
C50.051 (5)0.035 (4)0.043 (5)0.005 (4)0.003 (4)0.003 (4)
C60.080 (6)0.047 (4)0.055 (5)0.007 (4)0.008 (6)0.015 (5)
C70.031 (4)0.052 (5)0.041 (5)0.002 (4)0.003 (4)0.011 (4)
C80.037 (5)0.049 (5)0.035 (4)0.001 (4)0.003 (3)0.007 (4)
C90.045 (5)0.058 (5)0.044 (5)0.002 (4)0.006 (4)0.002 (4)
C100.045 (5)0.045 (5)0.040 (5)0.009 (4)0.012 (4)0.001 (4)
C110.032 (4)0.043 (5)0.050 (5)0.004 (3)0.008 (4)0.003 (4)
C120.057 (6)0.052 (6)0.074 (8)0.007 (4)0.007 (5)0.020 (5)
C130.066 (6)0.050 (5)0.049 (5)0.009 (5)0.016 (5)0.002 (4)
C140.055 (6)0.064 (6)0.046 (6)0.003 (4)0.016 (5)0.003 (4)
C150.056 (6)0.071 (7)0.046 (6)0.012 (5)0.005 (5)0.002 (5)
C160.057 (6)0.072 (7)0.039 (5)0.001 (5)0.002 (4)0.005 (5)
Geometric parameters (Å, º) top
Sn1—C142.095 (9)C4—C51.374 (12)
Sn1—C132.100 (9)C4—C61.496 (11)
Sn1—O12.287 (5)C5—H50.9300
Sn1—O4i2.311 (6)C6—H6A0.9600
Sn1—O32.327 (6)C6—H6B0.9600
Sn1—N12.487 (7)C6—H6C0.9600
Sn1—N32.496 (7)C7—C81.501 (12)
Sn2—C152.087 (10)C8—C91.384 (12)
Sn2—C162.117 (11)C9—H90.9300
Sn2—O22.330 (6)C10—C111.404 (12)
Sn2—Cl22.393 (3)C10—C121.483 (12)
Sn2—Cl12.480 (2)C11—H110.9300
N1—C51.329 (10)C12—H12A0.9600
N1—C21.331 (11)C12—H12B0.9600
N2—C31.330 (12)C12—H12C0.9600
N2—C41.337 (12)C13—H13A0.9600
N3—C81.327 (10)C13—H13B0.9600
N3—C111.337 (11)C13—H13C0.9600
N4—C91.319 (11)C14—H14A0.9600
N4—C101.321 (11)C14—H14B0.9600
O1—C11.246 (9)C14—H14C0.9600
O2—C11.250 (10)C15—H15A0.9600
O3—C71.257 (11)C15—H15B0.9600
O4—C71.249 (10)C15—H15C0.9600
O4—Sn1ii2.311 (6)C16—H16A0.9600
C1—C21.495 (11)C16—H16B0.9600
C2—C31.375 (12)C16—H16C0.9600
C3—H30.9300
C14—Sn1—C13177.2 (4)N1—C5—C4122.8 (8)
C14—Sn1—O189.5 (3)N1—C5—H5118.6
C13—Sn1—O188.0 (3)C4—C5—H5118.6
C14—Sn1—O4i87.9 (3)C4—C6—H6A109.5
C13—Sn1—O4i93.2 (3)C4—C6—H6B109.5
O1—Sn1—O4i144.1 (2)H6A—C6—H6B109.5
C14—Sn1—O387.1 (3)C4—C6—H6C109.5
C13—Sn1—O395.7 (3)H6A—C6—H6C109.5
O1—Sn1—O3140.9 (2)H6B—C6—H6C109.5
O4i—Sn1—O374.8 (2)O4—C7—O3127.1 (8)
C14—Sn1—N187.8 (3)O4—C7—C8116.4 (8)
C13—Sn1—N190.0 (3)O3—C7—C8116.5 (7)
O1—Sn1—N168.8 (2)N3—C8—C9119.8 (8)
O4i—Sn1—N175.3 (2)N3—C8—C7116.9 (7)
O3—Sn1—N1149.8 (2)C9—C8—C7123.3 (8)
C14—Sn1—N393.5 (3)N4—C9—C8123.4 (8)
C13—Sn1—N387.2 (3)N4—C9—H9118.3
O1—Sn1—N374.1 (2)C8—C9—H9118.3
O4i—Sn1—N3141.8 (2)N4—C10—C11120.5 (8)
O3—Sn1—N367.2 (2)N4—C10—C12119.2 (8)
N1—Sn1—N3142.9 (2)C11—C10—C12120.2 (8)
C15—Sn2—C16144.5 (4)N3—C11—C10121.3 (8)
C15—Sn2—O283.1 (3)N3—C11—H11119.4
C16—Sn2—O286.0 (4)C10—C11—H11119.4
C15—Sn2—Cl2106.6 (3)C10—C12—H12A109.5
C16—Sn2—Cl2106.3 (3)C10—C12—H12B109.5
O2—Sn2—Cl286.60 (19)H12A—C12—H12B109.5
C15—Sn2—Cl195.4 (3)C10—C12—H12C109.5
C16—Sn2—Cl196.1 (3)H12A—C12—H12C109.5
O2—Sn2—Cl1177.9 (2)H12B—C12—H12C109.5
Cl2—Sn2—Cl192.40 (10)Sn1—C13—H13A109.5
C5—N1—C2116.2 (7)Sn1—C13—H13B109.5
C5—N1—Sn1131.3 (5)H13A—C13—H13B109.5
C2—N1—Sn1112.5 (5)Sn1—C13—H13C109.5
C3—N2—C4116.9 (8)H13A—C13—H13C109.5
C8—N3—C11117.8 (7)H13B—C13—H13C109.5
C8—N3—Sn1114.6 (5)Sn1—C14—H14A109.5
C11—N3—Sn1127.6 (5)Sn1—C14—H14B109.5
C9—N4—C10117.2 (8)H14A—C14—H14B109.5
C1—O1—Sn1122.4 (5)Sn1—C14—H14C109.5
C1—O2—Sn2135.6 (6)H14A—C14—H14C109.5
C7—O3—Sn1122.7 (5)H14B—C14—H14C109.5
C7—O4—Sn1ii132.5 (6)Sn2—C15—H15A109.5
O1—C1—O2126.6 (7)Sn2—C15—H15B109.5
O1—C1—C2118.1 (7)H15A—C15—H15B109.5
O2—C1—C2115.3 (7)Sn2—C15—H15C109.5
N1—C2—C3121.6 (8)H15A—C15—H15C109.5
N1—C2—C1117.7 (8)H15B—C15—H15C109.5
C3—C2—C1120.6 (8)Sn2—C16—H16A109.5
N2—C3—C2121.8 (9)Sn2—C16—H16B109.5
N2—C3—H3119.1H16A—C16—H16B109.5
C2—C3—H3119.1Sn2—C16—H16C109.5
N2—C4—C5120.6 (8)H16A—C16—H16C109.5
N2—C4—C6118.5 (8)H16B—C16—H16C109.5
C5—C4—C6120.8 (8)
Symmetry codes: (i) x, y+1, z1/2; (ii) x, y+1, z+1/2.
 

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