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The mol­ecule of the title compound, [Sn(C9H3NO4)(CH3)2(C12H8N2)], occupies a special position on a mirror plane, which passes through the Sn, pyridine N and para-C, and two methyl C atoms. The Sn atom has a distorted penta­gonal-bipyramidal coordination, with the equatorial plane formed by two N atoms of 1,10-phenanthroline [Sn-N = 2.4754 (18) Å], and the pyridine N and two carboxyl­ate O atoms of pyridine-2,6-dicarboxyl­ate [Sn-N = 2.288 (2) Å and Sn-O = 2.2614 (15) Å]; two methyl groups occupy the axial positions [Sn-C = 2.112 (3) and 2.096 (4) Å, and C-Sn-C = 174.26 (13)°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805037748/ya6270sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805037748/ya6270Isup2.hkl
Contains datablock I

CCDC reference: 283418

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.025
  • wR factor = 0.059
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); 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.

Dimethyl(1,10-phenanthroline)(pyridine-2,6-dicarboxylato)tin top
Crystal data top
[Sn(C9H3NO4)(CH3)2(C12H8N2)]F(000) = 492
Mr = 494.07Dx = 1.739 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
a = 7.4595 (8) ÅCell parameters from 4502 reflections
b = 13.754 (1) Åθ = 2.2–25.2°
c = 9.723 (1) ŵ = 1.39 mm1
β = 108.914 (1)°T = 295 K
V = 943.75 (17) Å3Plate, colorless
Z = 20.16 × 0.14 × 0.03 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2257 independent reflections
Radiation source: fine-focus sealed tube2099 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.808, Tmax = 0.959k = 1717
10848 measured reflectionsl = 1212
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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0339P)2]
where P = (Fo2 + 2Fc2)/3
2257 reflections(Δ/σ)max < 0.001
153 parametersΔρmax = 0.46 e Å3
10 restraintsΔρmin = 0.44 e Å3
Special details top

Experimental. The elemental analyses were performed with a Perkin–Elmer PE2400II instrument.

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
Sn10.19651 (3)0.25000.104475 (19)0.03814 (9)
O10.1735 (2)0.09596 (11)0.17834 (17)0.0523 (4)
O20.1513 (3)0.00151 (13)0.3546 (2)0.0693 (5)
N10.2786 (2)0.15089 (14)0.07911 (19)0.0443 (4)
N20.1119 (3)0.25000.3106 (3)0.0393 (5)
C10.4889 (5)0.25000.2235 (4)0.0457 (7)
H1A0.564 (4)0.25000.160 (3)0.053 (10)*
H1B0.516 (4)0.1931 (7)0.283 (2)0.076 (9)*
C20.0859 (5)0.25000.0326 (4)0.0651 (10)
H2A0.179 (6)0.25000.017 (5)0.121 (19)*
H2B0.102 (4)0.1932 (7)0.093 (3)0.092 (10)*
C30.1390 (3)0.07780 (17)0.2958 (3)0.0481 (5)
C40.0829 (3)0.16528 (16)0.3665 (2)0.0419 (5)
C50.0103 (3)0.16280 (18)0.4807 (2)0.0482 (5)
H50.01220.10400.51940.058*
C60.0277 (4)0.25000.5353 (3)0.0510 (8)
H60.07970.25000.61030.061*
C70.2622 (4)0.05562 (19)0.0889 (3)0.0534 (6)
H70.20170.02370.03200.064*
C80.3319 (4)0.0005 (2)0.1813 (3)0.0621 (7)
H80.31660.06670.18620.074*
C90.4225 (3)0.0462 (2)0.2641 (3)0.0617 (7)
H90.47340.01010.32340.074*
C100.4387 (3)0.1475 (2)0.2597 (2)0.0531 (6)
C110.3616 (3)0.19811 (17)0.1666 (2)0.0441 (5)
C120.5212 (3)0.2012 (2)0.3495 (3)0.0647 (7)
H120.57590.16800.40920.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.04170 (13)0.04257 (13)0.03360 (12)0.0000.01695 (9)0.000
O10.0729 (11)0.0451 (8)0.0507 (9)0.0053 (7)0.0364 (8)0.0024 (7)
O20.0933 (14)0.0509 (10)0.0828 (13)0.0050 (9)0.0548 (12)0.0158 (9)
N10.0492 (10)0.0493 (11)0.0367 (9)0.0009 (8)0.0171 (8)0.0049 (8)
N20.0391 (13)0.0461 (14)0.0360 (12)0.0000.0171 (10)0.000
C10.0446 (17)0.0476 (18)0.0449 (17)0.0000.0143 (14)0.000
C20.0450 (19)0.096 (3)0.052 (2)0.0000.0117 (17)0.000
C30.0471 (12)0.0502 (13)0.0530 (13)0.0049 (10)0.0246 (10)0.0030 (10)
C40.0377 (10)0.0525 (12)0.0375 (10)0.0018 (9)0.0151 (9)0.0033 (9)
C50.0433 (12)0.0635 (14)0.0420 (12)0.0042 (10)0.0194 (10)0.0060 (10)
C60.0425 (17)0.076 (2)0.0411 (17)0.0000.0225 (14)0.000
C70.0605 (14)0.0531 (14)0.0479 (13)0.0021 (11)0.0193 (11)0.0090 (10)
C80.0652 (16)0.0621 (15)0.0561 (15)0.0070 (12)0.0157 (13)0.0165 (12)
C90.0572 (14)0.0843 (19)0.0436 (13)0.0164 (13)0.0160 (11)0.0155 (12)
C100.0397 (11)0.0818 (17)0.0365 (11)0.0086 (11)0.0104 (9)0.0068 (11)
C110.0364 (10)0.0653 (13)0.0302 (10)0.0009 (9)0.0101 (8)0.0031 (9)
C120.0474 (13)0.110 (2)0.0413 (12)0.0035 (12)0.0210 (10)0.0064 (12)
Geometric parameters (Å, º) top
Sn1—C22.096 (4)C3—C41.511 (3)
Sn1—C12.112 (3)C4—C51.385 (3)
Sn1—O12.2614 (15)C5—C61.378 (3)
Sn1—O1i2.2614 (15)C5—H50.9300
Sn1—N22.288 (2)C6—C5i1.378 (3)
Sn1—N12.4754 (18)C6—H60.9300
Sn1—N1i2.4754 (18)C7—C81.399 (4)
O1—C31.274 (3)C7—H70.9300
O2—C31.221 (3)C8—C91.360 (4)
N1—C71.317 (3)C8—H80.9300
N1—C111.367 (3)C9—C101.398 (4)
N2—C41.333 (2)C9—H90.9300
N2—C4i1.333 (2)C10—C111.405 (3)
C1—H1A0.959 (16)C10—C121.427 (4)
C1—H1B0.957 (12)C11—C11i1.428 (5)
C2—H2A0.97 (5)C12—C12i1.342 (6)
C2—H2B0.962 (13)C12—H120.9300
C2—Sn1—C1174.26 (13)Sn1—C2—H2B106.8 (18)
C2—Sn1—O192.17 (6)H2A—C2—H2B109.8 (17)
C1—Sn1—O189.83 (5)O2—C3—O1126.0 (2)
C2—Sn1—O1i92.17 (6)O2—C3—C4119.2 (2)
C1—Sn1—O1i89.83 (5)O1—C3—C4114.73 (19)
O1—Sn1—O1i139.08 (8)N2—C4—C5120.4 (2)
C2—Sn1—N292.93 (12)N2—C4—C3113.88 (18)
C1—Sn1—N292.81 (11)C5—C4—C3125.7 (2)
O1—Sn1—N269.57 (4)C6—C5—C4118.1 (2)
O1i—Sn1—N269.57 (4)C6—C5—H5121.0
C2—Sn1—N188.50 (10)C4—C5—H5121.0
C1—Sn1—N186.71 (9)C5—C6—C5i121.0 (3)
O1—Sn1—N177.00 (6)C5—C6—H6119.5
O1i—Sn1—N1143.79 (6)C5i—C6—H6119.5
N2—Sn1—N1146.57 (5)N1—C7—C8122.7 (3)
C2—Sn1—N1i88.50 (10)N1—C7—H7118.6
C1—Sn1—N1i86.71 (9)C8—C7—H7118.6
O1—Sn1—N1i143.79 (6)C9—C8—C7119.3 (3)
O1i—Sn1—N1i77.00 (6)C9—C8—H8120.4
N2—Sn1—N1i146.57 (5)C7—C8—H8120.4
N1—Sn1—N1i66.83 (9)C8—C9—C10119.8 (2)
C3—O1—Sn1121.77 (14)C8—C9—H9120.1
C7—N1—C11118.6 (2)C10—C9—H9120.1
C7—N1—Sn1124.14 (16)C9—C10—C11117.7 (2)
C11—N1—Sn1117.04 (15)C9—C10—C12123.2 (2)
C4—N2—C4i121.9 (2)C11—C10—C12119.0 (3)
C4—N2—Sn1119.00 (12)N1—C11—C10121.9 (2)
C4i—N2—Sn1119.00 (12)N1—C11—C11i118.36 (13)
Sn1—C1—H1A111 (2)C10—C11—C11i119.73 (16)
Sn1—C1—H1B107.9 (16)C12i—C12—C10121.22 (16)
H1A—C1—H1B110.0 (14)C12i—C12—H12119.4
Sn1—C2—H2A115 (3)C10—C12—H12119.4
C2—Sn1—O1—C396.5 (2)Sn1—O1—C3—O2168.6 (2)
C1—Sn1—O1—C388.88 (19)Sn1—O1—C3—C49.8 (3)
O1i—Sn1—O1—C30.7 (3)C4i—N2—C4—C53.8 (4)
N2—Sn1—O1—C34.18 (17)Sn1—N2—C4—C5172.42 (15)
N1—Sn1—O1—C3175.54 (18)C4i—N2—C4—C3175.22 (17)
N1i—Sn1—O1—C3173.06 (15)Sn1—N2—C4—C38.5 (3)
C2—Sn1—N1—C784.32 (19)O2—C3—C4—N2166.8 (2)
C1—Sn1—N1—C798.85 (19)O1—C3—C4—N211.7 (3)
O1—Sn1—N1—C78.26 (18)O2—C3—C4—C512.2 (4)
O1i—Sn1—N1—C7175.96 (16)O1—C3—C4—C5169.3 (2)
N2—Sn1—N1—C78.7 (2)N2—C4—C5—C61.0 (3)
N1i—Sn1—N1—C7173.33 (16)C3—C4—C5—C6177.9 (2)
C2—Sn1—N1—C11101.72 (16)C4—C5—C6—C5i1.8 (5)
C1—Sn1—N1—C1175.11 (15)C11—N1—C7—C82.3 (3)
O1—Sn1—N1—C11165.70 (16)Sn1—N1—C7—C8171.62 (18)
O1i—Sn1—N1—C1110.1 (2)N1—C7—C8—C90.7 (4)
N2—Sn1—N1—C11165.22 (15)C7—C8—C9—C102.3 (4)
N1i—Sn1—N1—C1112.71 (17)C8—C9—C10—C110.9 (4)
C2—Sn1—N2—C488.17 (18)C8—C9—C10—C12176.1 (2)
C1—Sn1—N2—C491.83 (18)C7—N1—C11—C103.6 (3)
O1—Sn1—N2—C43.06 (17)Sn1—N1—C11—C10170.66 (15)
O1i—Sn1—N2—C4179.4 (2)C7—N1—C11—C11i173.64 (15)
N1—Sn1—N2—C43.6 (3)Sn1—N1—C11—C11i12.05 (15)
N1i—Sn1—N2—C4179.90 (13)C9—C10—C11—N12.1 (3)
C2—Sn1—N2—C4i88.17 (18)C12—C10—C11—N1179.2 (2)
C1—Sn1—N2—C4i91.83 (18)C9—C10—C11—C11i175.17 (15)
O1—Sn1—N2—C4i179.4 (2)C12—C10—C11—C11i1.9 (2)
O1i—Sn1—N2—C4i3.06 (17)C9—C10—C12—C12i174.97 (17)
N1—Sn1—N2—C4i179.90 (13)C11—C10—C12—C12i2.0 (2)
N1i—Sn1—N2—C4i3.6 (3)
Symmetry code: (i) x, y+1/2, z.
 

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