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The title compound, [Sn(C6H5)2(C8H6N2O2)], features a five-coordinate C2NO2 coordination geometry for Sn that is inter­mediate between trigonal-bipyramidal and square-pyramidal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012767/hb2334sup1.cif
Contains datablocks general, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012767/hb2334Isup2.hkl
Contains datablock I

CCDC reference: 643649

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.022
  • wR factor = 0.058
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

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Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT480_ALERT_4_C Long H...A H-Bond Reported H19 .. O1 .. 2.67 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) & DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C20H16N2O2SnZ = 2
Mr = 435.04F(000) = 432
Triclinic, P1Dx = 1.680 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9903 (5) ÅCell parameters from 7180 reflections
b = 9.0639 (5) Åθ = 2.4–29.6°
c = 11.8622 (7) ŵ = 1.50 mm1
α = 77.277 (1)°T = 100 K
β = 74.324 (1)°Block, yellow
γ = 68.869 (1)°0.49 × 0.43 × 0.39 mm
V = 859.93 (8) Å3
Data collection top
Bruker SMART CCD
diffractometer
3297 independent reflections
Radiation source: fine-focus sealed tube3196 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 26.0°, θmin = 2.4°
ω scansh = 1111
Absorption correction: multi-scan
SADABS (Bruker, 2006)
k = 1110
Tmin = 0.459, Tmax = 0.557l = 1414
6594 measured reflections
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)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0258P)2 + 0.9175P]
where P = (Fo2 + 2Fc2)/3
3297 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = 0.74 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
Sn0.073101 (18)0.179092 (18)0.246058 (13)0.01552 (7)
O10.2676 (2)0.0444 (2)0.24888 (15)0.0215 (4)
O20.1012 (2)0.3823 (2)0.30705 (15)0.0201 (4)
N10.2437 (3)0.0236 (3)0.44564 (19)0.0217 (4)
N20.1199 (2)0.1213 (2)0.42263 (17)0.0166 (4)
C10.3058 (3)0.0949 (3)0.3519 (2)0.0195 (5)
H10.38850.19540.35950.023*
C20.0467 (3)0.2021 (3)0.5111 (2)0.0182 (5)
H20.08540.15960.58230.022*
C30.0863 (3)0.3487 (3)0.5121 (2)0.0176 (5)
C40.1546 (3)0.4316 (3)0.4123 (2)0.0169 (5)
C50.2846 (3)0.5750 (3)0.4244 (2)0.0219 (5)
H50.33050.63240.35790.026*
C60.3469 (3)0.6339 (3)0.5313 (2)0.0251 (6)
H60.43500.73100.53760.030*
C70.2814 (3)0.5518 (3)0.6308 (2)0.0228 (5)
H70.32550.59210.70440.027*
C80.1529 (3)0.4126 (3)0.6205 (2)0.0209 (5)
H80.10750.35780.68770.025*
C90.0923 (3)0.0795 (3)0.2184 (2)0.0169 (5)
C100.2589 (3)0.1418 (3)0.2658 (2)0.0198 (5)
H100.29800.23040.30830.024*
C110.3678 (3)0.0742 (3)0.2509 (2)0.0239 (5)
H110.48070.11540.28470.029*
C120.3118 (3)0.0530 (3)0.1867 (2)0.0232 (5)
H120.38670.09800.17590.028*
C130.1469 (3)0.1150 (3)0.1383 (2)0.0208 (5)
H130.10900.20180.09400.025*
C140.0366 (3)0.0496 (3)0.1545 (2)0.0190 (5)
H140.07640.09280.12220.023*
C150.2105 (3)0.3034 (3)0.1105 (2)0.0167 (5)
C160.1485 (3)0.4688 (3)0.0857 (2)0.0219 (5)
H160.04810.52540.13200.026*
C170.2329 (3)0.5521 (3)0.0067 (2)0.0259 (6)
H170.19020.66500.02330.031*
C180.3795 (3)0.4691 (3)0.0743 (2)0.0265 (6)
H180.43660.52550.13780.032*
C190.4429 (3)0.3049 (3)0.0498 (2)0.0269 (6)
H190.54380.24900.09600.032*
C200.3588 (3)0.2211 (3)0.0427 (2)0.0214 (5)
H200.40250.10830.05950.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn0.01591 (10)0.01400 (10)0.01511 (9)0.00329 (7)0.00194 (6)0.00308 (6)
O10.0194 (8)0.0179 (9)0.0227 (9)0.0005 (7)0.0027 (7)0.0052 (7)
O20.0207 (8)0.0184 (9)0.0173 (8)0.0005 (7)0.0038 (7)0.0050 (7)
N10.0217 (11)0.0159 (11)0.0248 (11)0.0023 (9)0.0081 (9)0.0001 (9)
N20.0176 (10)0.0138 (10)0.0182 (10)0.0059 (8)0.0041 (8)0.0003 (8)
C10.0153 (11)0.0123 (12)0.0278 (13)0.0025 (10)0.0057 (10)0.0015 (10)
C20.0236 (12)0.0185 (12)0.0157 (11)0.0127 (10)0.0039 (9)0.0011 (9)
C30.0206 (12)0.0166 (12)0.0172 (11)0.0102 (10)0.0003 (9)0.0034 (9)
C40.0181 (11)0.0165 (12)0.0161 (11)0.0079 (10)0.0009 (9)0.0041 (9)
C50.0195 (12)0.0207 (13)0.0232 (12)0.0027 (10)0.0039 (10)0.0054 (10)
C60.0183 (12)0.0259 (14)0.0295 (14)0.0045 (11)0.0020 (10)0.0134 (11)
C70.0251 (13)0.0261 (14)0.0182 (12)0.0125 (11)0.0050 (10)0.0098 (10)
C80.0271 (13)0.0211 (13)0.0163 (11)0.0131 (11)0.0010 (10)0.0017 (10)
C90.0185 (11)0.0166 (12)0.0137 (10)0.0049 (10)0.0037 (9)0.0009 (9)
C100.0218 (12)0.0185 (12)0.0179 (11)0.0053 (10)0.0016 (9)0.0054 (10)
C110.0182 (12)0.0267 (14)0.0256 (13)0.0076 (11)0.0008 (10)0.0074 (11)
C120.0257 (13)0.0227 (14)0.0243 (13)0.0110 (11)0.0060 (10)0.0030 (11)
C130.0267 (13)0.0153 (12)0.0199 (12)0.0048 (10)0.0044 (10)0.0057 (10)
C140.0193 (12)0.0185 (12)0.0158 (11)0.0033 (10)0.0019 (9)0.0025 (9)
C150.0184 (11)0.0184 (12)0.0149 (11)0.0071 (10)0.0031 (9)0.0036 (9)
C160.0219 (12)0.0214 (13)0.0192 (12)0.0038 (11)0.0030 (10)0.0031 (10)
C170.0314 (14)0.0203 (14)0.0249 (13)0.0102 (12)0.0057 (11)0.0019 (11)
C180.0296 (14)0.0297 (15)0.0221 (13)0.0164 (12)0.0016 (11)0.0007 (11)
C190.0228 (13)0.0328 (16)0.0246 (13)0.0110 (12)0.0037 (11)0.0104 (12)
C200.0211 (12)0.0214 (13)0.0218 (12)0.0060 (11)0.0028 (10)0.0070 (10)
Geometric parameters (Å, º) top
Sn—O12.1470 (18)C9—C101.397 (3)
Sn—O22.0654 (17)C9—C141.399 (3)
Sn—N22.162 (2)C10—C111.392 (4)
Sn—C92.120 (2)C10—H100.9500
Sn—C152.125 (2)C11—C121.387 (4)
O1—C11.299 (3)C11—H110.9500
O2—C41.325 (3)C12—C131.388 (4)
N1—C11.299 (3)C12—H120.9500
N1—N21.411 (3)C13—C141.396 (4)
N2—C21.299 (3)C13—H130.9500
C1—H10.9500C14—H140.9500
C2—C31.431 (4)C15—C161.391 (4)
C2—H20.9500C15—C201.396 (3)
C3—C41.418 (3)C16—C171.395 (4)
C3—C81.418 (3)C16—H160.9500
C4—C51.405 (3)C17—C181.387 (4)
C5—C61.381 (4)C17—H170.9500
C5—H50.9500C18—C191.383 (4)
C6—C71.402 (4)C18—H180.9500
C6—H60.9500C19—C201.397 (4)
C7—C81.371 (4)C19—H190.9500
C7—H70.9500C20—H200.9500
C8—H80.9500
O2—Sn—C996.23 (8)C7—C8—H8119.2
O2—Sn—C1595.10 (8)C3—C8—H8119.2
O1—Sn—O2158.42 (7)C10—C9—C14119.4 (2)
O1—Sn—N273.94 (7)C10—C9—Sn119.82 (18)
O2—Sn—N284.49 (7)C14—C9—Sn120.82 (17)
C9—Sn—C15124.62 (9)C11—C10—C9120.2 (2)
C9—Sn—O193.72 (8)C11—C10—H10119.9
C15—Sn—O194.91 (8)C9—C10—H10119.9
C9—Sn—N2115.22 (8)C12—C11—C10120.1 (2)
C15—Sn—N2119.75 (8)C12—C11—H11119.9
C1—O1—Sn112.38 (15)C10—C11—H11119.9
C4—O2—Sn132.88 (16)C13—C12—C11120.3 (2)
C1—N1—N2110.2 (2)C13—C12—H12119.9
C2—N2—N1115.7 (2)C11—C12—H12119.9
C2—N2—Sn128.20 (17)C12—C13—C14119.9 (2)
N1—N2—Sn116.09 (14)C12—C13—H13120.0
O1—C1—N1127.4 (2)C14—C13—H13120.0
O1—C1—H1116.3C13—C14—C9120.1 (2)
N1—C1—H1116.3C13—C14—H14119.9
N2—C2—C3126.6 (2)C9—C14—H14119.9
N2—C2—H2116.7C16—C15—C20119.5 (2)
C3—C2—H2116.7C16—C15—Sn119.48 (17)
C4—C3—C8118.8 (2)C20—C15—Sn120.95 (18)
C4—C3—C2124.0 (2)C15—C16—C17120.4 (2)
C8—C3—C2117.1 (2)C15—C16—H16119.8
O2—C4—C5117.7 (2)C17—C16—H16119.8
O2—C4—C3123.6 (2)C18—C17—C16119.7 (3)
C5—C4—C3118.7 (2)C18—C17—H17120.2
C6—C5—C4121.0 (2)C16—C17—H17120.2
C6—C5—H5119.5C19—C18—C17120.4 (2)
C4—C5—H5119.5C19—C18—H18119.8
C5—C6—C7120.7 (2)C17—C18—H18119.8
C5—C6—H6119.7C18—C19—C20120.1 (2)
C7—C6—H6119.7C18—C19—H19119.9
C8—C7—C6119.2 (2)C20—C19—H19119.9
C8—C7—H7120.4C15—C20—C19119.9 (2)
C6—C7—H7120.4C15—C20—H20120.1
C7—C8—C3121.5 (2)C19—C20—H20120.1
O2—Sn—O1—C13.5 (3)C4—C3—C8—C70.2 (4)
C9—Sn—O1—C1113.83 (16)C2—C3—C8—C7179.5 (2)
C15—Sn—O1—C1120.93 (16)O2—Sn—C9—C1013.3 (2)
N2—Sn—O1—C11.36 (15)C15—Sn—C9—C10113.89 (19)
C9—Sn—O2—C4110.4 (2)O1—Sn—C9—C10147.53 (19)
C15—Sn—O2—C4123.9 (2)N2—Sn—C9—C1073.5 (2)
O1—Sn—O2—C46.5 (3)O2—Sn—C9—C14167.59 (19)
N2—Sn—O2—C44.4 (2)C15—Sn—C9—C1467.0 (2)
C1—N1—N2—C2178.9 (2)O1—Sn—C9—C1431.6 (2)
C1—N1—N2—Sn0.2 (2)N2—Sn—C9—C14105.59 (19)
O2—Sn—N2—C21.3 (2)C14—C9—C10—C110.9 (4)
C9—Sn—N2—C293.0 (2)Sn—C9—C10—C11178.21 (19)
C15—Sn—N2—C294.0 (2)C9—C10—C11—C121.4 (4)
O1—Sn—N2—C2179.5 (2)C10—C11—C12—C130.8 (4)
O2—Sn—N2—N1179.85 (16)C11—C12—C13—C140.3 (4)
C9—Sn—N2—N185.85 (17)C12—C13—C14—C90.8 (4)
C15—Sn—N2—N187.10 (17)C10—C9—C14—C130.1 (4)
O1—Sn—N2—N10.65 (14)Sn—C9—C14—C13179.27 (18)
Sn—O1—C1—N12.3 (3)O2—Sn—C15—C168.3 (2)
N2—N1—C1—O11.7 (3)C9—Sn—C15—C1692.9 (2)
N1—N2—C2—C3177.4 (2)O1—Sn—C15—C16169.15 (19)
Sn—N2—C2—C31.5 (3)N2—Sn—C15—C1694.9 (2)
N2—C2—C3—C42.6 (4)O2—Sn—C15—C20174.43 (19)
N2—C2—C3—C8177.1 (2)C9—Sn—C15—C2084.4 (2)
Sn—O2—C4—C5176.08 (16)O1—Sn—C15—C2013.6 (2)
Sn—O2—C4—C34.7 (3)N2—Sn—C15—C2087.9 (2)
C8—C3—C4—O2179.9 (2)C20—C15—C16—C170.5 (4)
C2—C3—C4—O20.5 (4)Sn—C15—C16—C17176.82 (19)
C8—C3—C4—C50.7 (3)C15—C16—C17—C180.1 (4)
C2—C3—C4—C5179.7 (2)C16—C17—C18—C190.6 (4)
O2—C4—C5—C6179.9 (2)C17—C18—C19—C200.6 (4)
C3—C4—C5—C60.8 (4)C16—C15—C20—C190.5 (4)
C4—C5—C6—C70.1 (4)Sn—C15—C20—C19176.75 (19)
C5—C6—C7—C80.8 (4)C18—C19—C20—C150.0 (4)
C6—C7—C8—C30.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cgi0.952.933.872 (3)172
C19—H19···O1ii0.952.673.554 (3)154
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z.
 

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