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The coordination geometry at the Sn atom in the title compound, [Sn(C6H5)2(C9H6NO)2], is distorted cis-octa­hedral, in which the two phenyl ligands are cis to one another and trans to the N atoms of the oxinate ligands. This arrangement brings the oxinate O atoms into a trans relationship and is the geometry adopted most frequently by diorganotin(IV) oxinates. The O...O vector in the mol­ecule is almost parallel to the plane of every ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031277/lh6330sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031277/lh6330Isup2.hkl
Contains datablock I

CCDC reference: 262230

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.091
  • Data-to-parameter ratio = 22.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.90
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 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 (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

cis-Bis(8-hydroxyquinolinato-κ2N,O)diphenyltin(IV) top
Crystal data top
[Sn(C6H5)2(C9H6NO)2]F(000) = 1128
Mr = 561.12Dx = 1.524 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 90230 reflections
a = 12.8111 (3) Åθ = 2.0–30.0°
b = 14.8721 (4) ŵ = 1.07 mm1
c = 12.8378 (3) ÅT = 160 K
β = 91.3964 (14)°Tablet, yellow
V = 2445.23 (10) Å30.25 × 0.25 × 0.07 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
7135 independent reflections
Radiation source: Nonius FR590 sealed tube generator5326 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.079
Detector resolution: 9 pixels mm-1θmax = 30.0°, θmin = 2.1°
ω scans with κ offsetsh = 1618
Absorption correction: multi-scan
(Blessing, 1995)
k = 2020
Tmin = 0.697, Tmax = 0.933l = 1818
68827 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0412P)2 + 2.0301P]
where P = (Fo2 + 2Fc2)/3
7130 reflections(Δ/σ)max = 0.003
316 parametersΔρmax = 1.67 e Å3
0 restraintsΔρmin = 1.15 e Å3
Special details top

Experimental. Solvent used: acetone Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 1.060 (1) Frames collected: 413 Seconds exposure per frame: 15 Degrees rotation per frame: 1.9 Crystal-Detector distance (mm): 30.0

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
Sn0.752739 (12)0.218737 (12)0.765126 (13)0.02081 (6)
O10.71802 (14)0.34817 (12)0.81518 (13)0.0257 (4)
O20.81095 (13)0.08834 (12)0.77604 (14)0.0251 (4)
N10.70748 (17)0.20349 (15)0.93898 (17)0.0240 (5)
N20.91164 (17)0.23229 (14)0.85554 (16)0.0230 (5)
C10.7041 (2)0.13076 (19)0.9977 (2)0.0294 (6)
H10.72540.07490.96930.035*
C20.6701 (2)0.1333 (2)1.1009 (2)0.0342 (6)
H20.66900.08001.14160.041*
C30.6385 (2)0.2135 (2)1.1422 (2)0.0325 (6)
H30.61430.21561.21150.039*
C40.6418 (2)0.29291 (19)1.0826 (2)0.0278 (6)
C50.6118 (2)0.3787 (2)1.1172 (2)0.0337 (6)
H50.58810.38661.18610.040*
C60.6170 (2)0.4507 (2)1.0513 (2)0.0342 (6)
H60.59590.50811.07550.041*
C70.6529 (2)0.4425 (2)0.9484 (2)0.0304 (6)
H70.65620.49410.90490.037*
C80.6829 (2)0.35999 (18)0.91136 (19)0.0240 (5)
C90.67753 (19)0.28407 (17)0.97958 (19)0.0222 (5)
C100.9595 (2)0.30456 (19)0.8932 (2)0.0289 (6)
H100.92430.36070.89030.035*
C111.0603 (2)0.3008 (2)0.9373 (2)0.0327 (6)
H111.09280.35390.96340.039*
C121.1117 (2)0.2205 (2)0.9427 (2)0.0321 (6)
H121.18030.21780.97240.039*
C131.0634 (2)0.14145 (19)0.9043 (2)0.0277 (6)
C141.1090 (2)0.0555 (2)0.9057 (2)0.0354 (6)
H141.17760.04740.93390.042*
C151.0544 (2)0.0164 (2)0.8663 (2)0.0371 (7)
H151.08560.07430.86870.044*
C160.9528 (2)0.00696 (19)0.8221 (2)0.0297 (6)
H160.91690.05820.79550.036*
C170.9058 (2)0.07591 (17)0.81751 (19)0.0236 (5)
C180.96123 (19)0.15106 (18)0.86047 (18)0.0230 (5)
C190.82950 (19)0.26954 (17)0.62966 (19)0.0228 (5)
C200.8477 (2)0.36072 (19)0.6168 (2)0.0290 (6)
H200.82740.40160.66950.035*
C210.8953 (2)0.3936 (2)0.5280 (2)0.0339 (6)
H210.90820.45610.52080.041*
C220.9237 (2)0.3343 (2)0.4500 (2)0.0352 (7)
H220.95490.35640.38870.042*
C230.9069 (2)0.2437 (2)0.4616 (2)0.0356 (7)
H230.92700.20320.40850.043*
C240.8604 (2)0.21114 (19)0.5509 (2)0.0275 (6)
H240.84950.14830.55840.033*
C250.59985 (19)0.17132 (18)0.71828 (19)0.0239 (5)
C260.5792 (2)0.0805 (2)0.7029 (2)0.0350 (7)
H260.63320.03750.71390.042*
C270.4798 (2)0.0521 (2)0.6715 (3)0.0440 (8)
H270.46650.01030.66180.053*
C280.4003 (2)0.1134 (2)0.6542 (3)0.0402 (7)
H280.33280.09350.63210.048*
C290.4195 (2)0.2037 (2)0.6694 (2)0.0361 (7)
H290.36510.24640.65830.043*
C300.5183 (2)0.23205 (19)0.7008 (2)0.0292 (6)
H300.53090.29450.71080.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn0.02027 (10)0.02391 (10)0.01833 (9)0.00096 (7)0.00226 (6)0.00024 (6)
O10.0291 (9)0.0264 (10)0.0219 (9)0.0036 (8)0.0034 (7)0.0018 (7)
O20.0198 (9)0.0265 (9)0.0288 (10)0.0023 (7)0.0039 (7)0.0017 (7)
N10.0210 (11)0.0298 (12)0.0214 (10)0.0000 (9)0.0028 (8)0.0031 (8)
N20.0244 (11)0.0281 (12)0.0166 (10)0.0020 (9)0.0031 (8)0.0004 (8)
C10.0295 (14)0.0321 (15)0.0267 (13)0.0022 (12)0.0032 (11)0.0052 (11)
C20.0345 (15)0.0431 (17)0.0251 (14)0.0057 (13)0.0038 (11)0.0089 (12)
C30.0299 (14)0.0494 (18)0.0186 (12)0.0028 (13)0.0053 (10)0.0047 (12)
C40.0194 (12)0.0443 (17)0.0198 (12)0.0004 (12)0.0032 (9)0.0025 (11)
C50.0263 (14)0.0491 (18)0.0258 (14)0.0020 (13)0.0054 (11)0.0083 (12)
C60.0323 (15)0.0395 (16)0.0310 (15)0.0082 (13)0.0026 (12)0.0102 (12)
C70.0324 (15)0.0307 (14)0.0282 (14)0.0050 (12)0.0019 (11)0.0027 (11)
C80.0241 (12)0.0277 (14)0.0204 (12)0.0019 (11)0.0023 (9)0.0001 (10)
C90.0174 (11)0.0288 (13)0.0206 (12)0.0004 (10)0.0023 (9)0.0006 (10)
C100.0332 (15)0.0307 (14)0.0228 (13)0.0011 (12)0.0025 (11)0.0020 (10)
C110.0334 (15)0.0389 (17)0.0256 (14)0.0085 (13)0.0023 (11)0.0051 (11)
C120.0278 (14)0.0465 (17)0.0218 (13)0.0043 (13)0.0051 (10)0.0009 (11)
C130.0261 (13)0.0362 (16)0.0207 (12)0.0026 (12)0.0008 (10)0.0012 (10)
C140.0280 (15)0.0438 (17)0.0340 (15)0.0045 (13)0.0053 (12)0.0043 (13)
C150.0348 (16)0.0338 (16)0.0425 (17)0.0082 (13)0.0033 (13)0.0016 (13)
C160.0279 (14)0.0284 (14)0.0327 (15)0.0015 (12)0.0012 (11)0.0010 (11)
C170.0241 (12)0.0279 (14)0.0189 (12)0.0016 (11)0.0023 (9)0.0003 (9)
C180.0227 (12)0.0309 (14)0.0155 (11)0.0002 (11)0.0026 (9)0.0007 (9)
C190.0186 (11)0.0326 (15)0.0172 (11)0.0016 (10)0.0004 (9)0.0020 (9)
C200.0292 (14)0.0319 (15)0.0261 (13)0.0020 (12)0.0058 (10)0.0019 (11)
C210.0319 (15)0.0337 (16)0.0365 (16)0.0018 (13)0.0068 (12)0.0077 (12)
C220.0304 (14)0.0493 (19)0.0263 (14)0.0068 (14)0.0094 (11)0.0113 (12)
C230.0379 (16)0.0453 (17)0.0239 (14)0.0081 (14)0.0080 (12)0.0024 (12)
C240.0248 (13)0.0330 (15)0.0249 (13)0.0034 (11)0.0059 (10)0.0028 (10)
C250.0218 (12)0.0314 (14)0.0185 (12)0.0004 (11)0.0019 (9)0.0013 (10)
C260.0271 (14)0.0320 (16)0.0458 (18)0.0036 (12)0.0009 (12)0.0041 (12)
C270.0333 (17)0.0345 (17)0.064 (2)0.0027 (14)0.0037 (15)0.0114 (15)
C280.0241 (14)0.048 (2)0.0482 (19)0.0028 (14)0.0037 (13)0.0064 (15)
C290.0241 (14)0.0427 (18)0.0414 (17)0.0035 (13)0.0019 (12)0.0009 (13)
C300.0266 (14)0.0306 (16)0.0304 (14)0.0011 (11)0.0006 (11)0.0017 (11)
Geometric parameters (Å, º) top
Sn—O12.0809 (18)C12—H120.9500
Sn—O22.0812 (18)C13—C141.405 (4)
Sn—C252.154 (3)C13—C181.420 (4)
Sn—C192.155 (2)C14—C151.368 (4)
Sn—N22.327 (2)C14—H140.9500
Sn—N12.331 (2)C15—C161.414 (4)
O1—C81.336 (3)C15—H150.9500
O2—C171.328 (3)C16—C171.372 (4)
N1—C11.320 (3)C16—H160.9500
N1—C91.365 (3)C17—C181.428 (4)
N2—C101.323 (3)C19—C201.386 (4)
N2—C181.366 (3)C19—C241.398 (4)
C1—C21.405 (4)C20—C211.395 (4)
C1—H10.9500C20—H200.9500
C2—C31.370 (4)C21—C221.389 (4)
C2—H20.9500C21—H210.9500
C3—C41.408 (4)C22—C231.373 (5)
C3—H30.9500C22—H220.9500
C4—C51.408 (4)C23—C241.392 (4)
C4—C91.416 (3)C23—H230.9500
C5—C61.367 (4)C24—H240.9500
C5—H50.9500C25—C261.390 (4)
C6—C71.414 (4)C25—C301.395 (4)
C6—H60.9500C26—C271.392 (4)
C7—C81.375 (4)C26—H260.9500
C7—H70.9500C27—C281.382 (5)
C8—C91.432 (4)C27—H270.9500
C10—C111.398 (4)C28—C291.378 (4)
C10—H100.9500C28—H280.9500
C11—C121.366 (4)C29—C301.386 (4)
C11—H110.9500C29—H290.9500
C12—C131.412 (4)C30—H300.9500
O1—Sn—O2156.94 (7)C11—C12—H12119.9
O1—Sn—C25100.92 (9)C13—C12—H12119.9
O2—Sn—C2592.04 (9)C14—C13—C12125.1 (3)
O1—Sn—C1991.72 (8)C14—C13—C18118.4 (3)
O2—Sn—C19102.19 (8)C12—C13—C18116.5 (3)
C25—Sn—C19108.61 (9)C15—C14—C13119.8 (3)
O1—Sn—N287.53 (7)C15—C14—H14120.1
O2—Sn—N274.90 (7)C13—C14—H14120.1
C25—Sn—N2161.11 (9)C14—C15—C16121.9 (3)
C19—Sn—N287.78 (8)C14—C15—H15119.1
O1—Sn—N174.59 (7)C16—C15—H15119.1
O2—Sn—N186.68 (7)C17—C16—C15120.3 (3)
C25—Sn—N189.42 (8)C17—C16—H16119.8
C19—Sn—N1159.36 (9)C15—C16—H16119.8
N2—Sn—N176.46 (7)O2—C17—C16122.6 (2)
C8—O1—Sn119.11 (16)O2—C17—C18119.2 (2)
C17—O2—Sn118.67 (16)C16—C17—C18118.2 (2)
C1—N1—C9119.2 (2)N2—C18—C13122.1 (2)
C1—N1—Sn129.73 (18)N2—C18—C17116.6 (2)
C9—N1—Sn111.03 (16)C13—C18—C17121.3 (2)
C10—N2—C18119.4 (2)C20—C19—C24118.1 (2)
C10—N2—Sn130.15 (19)C20—C19—Sn121.34 (19)
C18—N2—Sn110.29 (16)C24—C19—Sn120.59 (19)
N1—C1—C2122.1 (3)C19—C20—C21121.2 (3)
N1—C1—H1118.9C19—C20—H20119.4
C2—C1—H1118.9C21—C20—H20119.4
C3—C2—C1119.3 (3)C22—C21—C20119.6 (3)
C3—C2—H2120.3C22—C21—H21120.2
C1—C2—H2120.3C20—C21—H21120.2
C2—C3—C4120.4 (2)C23—C22—C21120.0 (3)
C2—C3—H3119.8C23—C22—H22120.0
C4—C3—H3119.8C21—C22—H22120.0
C5—C4—C3125.2 (2)C22—C23—C24120.1 (3)
C5—C4—C9118.4 (3)C22—C23—H23119.9
C3—C4—C9116.4 (2)C24—C23—H23119.9
C6—C5—C4119.9 (3)C23—C24—C19120.9 (3)
C6—C5—H5120.1C23—C24—H24119.5
C4—C5—H5120.1C19—C24—H24119.5
C5—C6—C7122.1 (3)C26—C25—C30117.9 (3)
C5—C6—H6118.9C26—C25—Sn121.8 (2)
C7—C6—H6118.9C30—C25—Sn120.3 (2)
C8—C7—C6120.0 (3)C25—C26—C27120.4 (3)
C8—C7—H7120.0C25—C26—H26119.8
C6—C7—H7120.0C27—C26—H26119.8
O1—C8—C7122.7 (2)C28—C27—C26120.8 (3)
O1—C8—C9118.9 (2)C28—C27—H27119.6
C7—C8—C9118.3 (2)C26—C27—H27119.6
N1—C9—C4122.6 (2)C29—C28—C27119.5 (3)
N1—C9—C8116.1 (2)C29—C28—H28120.2
C4—C9—C8121.3 (2)C27—C28—H28120.2
N2—C10—C11122.1 (3)C28—C29—C30119.8 (3)
N2—C10—H10119.0C28—C29—H29120.1
C11—C10—H10119.0C30—C29—H29120.1
C12—C11—C10119.7 (3)C29—C30—C25121.7 (3)
C12—C11—H11120.2C29—C30—H30119.2
C10—C11—H11120.2C25—C30—H30119.2
C11—C12—C13120.3 (3)
O2—Sn—O1—C840.8 (3)C10—C11—C12—C130.2 (4)
C25—Sn—O1—C882.28 (18)C11—C12—C13—C14179.9 (3)
C19—Sn—O1—C8168.39 (18)C11—C12—C13—C180.3 (4)
N2—Sn—O1—C880.68 (18)C12—C13—C14—C15179.8 (3)
N1—Sn—O1—C84.05 (17)C18—C13—C14—C150.6 (4)
O1—Sn—O2—C1746.6 (3)C13—C14—C15—C161.0 (5)
C25—Sn—O2—C17171.21 (18)C14—C15—C16—C170.0 (5)
C19—Sn—O2—C1779.25 (18)Sn—O2—C17—C16176.0 (2)
N2—Sn—O2—C175.05 (17)Sn—O2—C17—C184.8 (3)
N1—Sn—O2—C1781.91 (17)C15—C16—C17—O2179.4 (2)
O1—Sn—N1—C1179.3 (2)C15—C16—C17—C181.4 (4)
O2—Sn—N1—C112.9 (2)C10—N2—C18—C130.5 (4)
C25—Sn—N1—C179.2 (2)Sn—N2—C18—C13175.02 (18)
C19—Sn—N1—C1129.4 (3)C10—N2—C18—C17179.4 (2)
N2—Sn—N1—C188.1 (2)Sn—N2—C18—C173.9 (3)
O1—Sn—N1—C93.14 (16)C14—C13—C18—N2179.6 (2)
O2—Sn—N1—C9169.57 (17)C12—C13—C18—N20.0 (4)
C25—Sn—N1—C998.35 (18)C14—C13—C18—C170.8 (4)
C19—Sn—N1—C953.1 (3)C12—C13—C18—C17178.8 (2)
N2—Sn—N1—C994.31 (17)O2—C17—C18—N20.1 (3)
O1—Sn—N2—C1015.5 (2)C16—C17—C18—N2179.3 (2)
O2—Sn—N2—C10179.5 (2)O2—C17—C18—C13179.0 (2)
C25—Sn—N2—C10132.9 (3)C16—C17—C18—C131.8 (4)
C19—Sn—N2—C1076.3 (2)O1—Sn—C19—C207.8 (2)
N1—Sn—N2—C1090.3 (2)O2—Sn—C19—C20153.7 (2)
O1—Sn—N2—C18169.59 (16)C25—Sn—C19—C20109.9 (2)
O2—Sn—N2—C184.66 (15)N2—Sn—C19—C2079.7 (2)
C25—Sn—N2—C1852.3 (3)N1—Sn—C19—C2039.8 (4)
C19—Sn—N2—C1898.59 (17)O1—Sn—C19—C24170.8 (2)
N1—Sn—N2—C1894.85 (16)O2—Sn—C19—C2427.7 (2)
C9—N1—C1—C20.4 (4)C25—Sn—C19—C2468.7 (2)
Sn—N1—C1—C2177.0 (2)N2—Sn—C19—C24101.7 (2)
N1—C1—C2—C30.5 (4)N1—Sn—C19—C24141.6 (2)
C1—C2—C3—C41.1 (4)C24—C19—C20—C210.1 (4)
C2—C3—C4—C5179.7 (3)Sn—C19—C20—C21178.5 (2)
C2—C3—C4—C90.8 (4)C19—C20—C21—C220.9 (4)
C3—C4—C5—C6179.0 (3)C20—C21—C22—C231.3 (4)
C9—C4—C5—C60.5 (4)C21—C22—C23—C240.6 (4)
C4—C5—C6—C70.7 (4)C22—C23—C24—C190.5 (4)
C5—C6—C7—C80.7 (4)C20—C19—C24—C230.8 (4)
Sn—O1—C8—C7176.4 (2)Sn—C19—C24—C23177.9 (2)
Sn—O1—C8—C94.5 (3)O1—Sn—C25—C26163.9 (2)
C6—C7—C8—O1179.6 (2)O2—Sn—C25—C263.1 (2)
C6—C7—C8—C90.5 (4)C19—Sn—C25—C26100.5 (2)
C1—N1—C9—C40.6 (4)N2—Sn—C25—C2648.6 (4)
Sn—N1—C9—C4177.2 (2)N1—Sn—C25—C2689.7 (2)
C1—N1—C9—C8179.8 (2)O1—Sn—C25—C3017.1 (2)
Sn—N1—C9—C82.0 (3)O2—Sn—C25—C30177.9 (2)
C5—C4—C9—N1179.5 (2)C19—Sn—C25—C3078.5 (2)
C3—C4—C9—N10.0 (4)N2—Sn—C25—C30132.4 (3)
C5—C4—C9—C80.3 (4)N1—Sn—C25—C3091.3 (2)
C3—C4—C9—C8179.2 (2)C30—C25—C26—C270.3 (4)
O1—C8—C9—N11.3 (3)Sn—C25—C26—C27179.3 (2)
C7—C8—C9—N1179.6 (2)C25—C26—C27—C280.5 (5)
O1—C8—C9—C4179.5 (2)C26—C27—C28—C290.7 (5)
C7—C8—C9—C40.3 (4)C27—C28—C29—C300.6 (5)
C18—N2—C10—C110.7 (4)C28—C29—C30—C250.3 (5)
Sn—N2—C10—C11173.81 (19)C26—C25—C30—C290.1 (4)
N2—C10—C11—C120.3 (4)Sn—C25—C30—C29179.2 (2)
 

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