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The title compound, [Sn(C6H5)3(C12H7N2OS2)]·0.5C2H6O, shows a distorted tetra­hedral coordination of the Sn atom. The crystal packing is determined by van der Waals inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046836/kp2059sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046836/kp2059Isup2.hkl
Contains datablock I

CCDC reference: 630040

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.012 Å
  • Disorder in solvent or counterion
  • R factor = 0.052
  • wR factor = 0.157
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C31 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); 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.

[6-(Furan-2-ylideneamino)-1,3-benzothiazole-2- thiolato-κS2]triphenyltin(IV) ethanol hemisolvate top
Crystal data top
[Sn(C6H5)3(C12H7N2OS2)]·0.5C2H6OZ = 2
Mr = 632.34F(000) = 638
Triclinic, P1Dx = 1.392 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.685 (2) ÅCell parameters from 1885 reflections
b = 13.204 (3) Åθ = 2.5–20.5°
c = 13.323 (3) ŵ = 1.01 mm1
α = 68.117 (4)°T = 298 K
β = 76.261 (4)°Block, yellow
γ = 75.145 (4)°0.21 × 0.16 × 0.11 mm
V = 1508.8 (6) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
5267 independent reflections
Radiation source: fine-focus sealed tube3313 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.816, Tmax = 0.897k = 1515
8021 measured reflectionsl = 158
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0829P)2]
where P = (Fo2 + 2Fc2)/3
5267 reflections(Δ/σ)max < 0.001
353 parametersΔρmax = 0.78 e Å3
39 restraintsΔρmin = 0.44 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*/UeqOcc. (<1)
Sn10.62923 (5)0.81468 (4)0.18265 (4)0.0602 (2)
N10.5352 (6)0.6989 (4)0.4207 (4)0.0567 (14)
N20.2618 (6)0.5531 (5)0.8550 (5)0.0645 (15)
O10.1176 (6)0.4928 (5)1.0755 (5)0.0963 (17)
O20.980 (2)0.9471 (13)0.5259 (16)0.174 (6)0.50
H21.00421.00760.49360.261*0.50
S10.7013 (2)0.52911 (16)0.53436 (15)0.0706 (5)
S20.78609 (19)0.65514 (16)0.29421 (15)0.0705 (5)
C10.6616 (7)0.6353 (6)0.4139 (5)0.0584 (17)
C20.4621 (7)0.6656 (5)0.5271 (5)0.0561 (16)
C30.3238 (7)0.7186 (6)0.5620 (6)0.0669 (19)
H30.27430.78040.51360.080*
C40.2639 (7)0.6769 (6)0.6694 (6)0.0646 (19)
H40.17110.71010.69310.078*
C50.3372 (7)0.5857 (5)0.7454 (6)0.0599 (17)
C60.4736 (7)0.5334 (5)0.7110 (6)0.0597 (17)
H60.52360.47220.75960.072*
C70.5335 (7)0.5751 (5)0.6018 (5)0.0531 (16)
C80.3296 (8)0.5010 (6)0.9343 (6)0.0618 (18)
H80.43010.48390.91990.074*
C90.2595 (8)0.4666 (6)1.0462 (6)0.0623 (18)
C100.3238 (7)0.4160 (7)1.1332 (6)0.068 (2)
H100.42280.39271.13370.082*
C110.2167 (11)0.4040 (7)1.2232 (7)0.088 (2)
H110.23090.36841.29570.106*
C120.0932 (10)0.4503 (7)1.1905 (7)0.080 (2)
H120.00370.45481.23530.096*
C130.5696 (7)0.9498 (6)0.2444 (5)0.0597 (17)
C140.4430 (9)1.0199 (7)0.2289 (7)0.089 (2)
H140.38191.00860.19140.107*
C150.4014 (11)1.1090 (8)0.2676 (9)0.119 (4)
H150.31291.15620.25580.143*
C160.4876 (11)1.1282 (8)0.3222 (8)0.100 (3)
H160.45951.18780.34830.119*
C170.6130 (12)1.0598 (9)0.3376 (10)0.124 (4)
H170.67381.07140.37520.148*
C180.6549 (10)0.9710 (8)0.2984 (9)0.109 (3)
H180.74420.92490.30950.131*
C190.7861 (7)0.8441 (5)0.0372 (5)0.0567 (16)
C200.8246 (8)0.9491 (6)0.0184 (7)0.081 (2)
H200.77771.00910.00510.097*
C210.9330 (10)0.9619 (7)0.1085 (7)0.098 (3)
H210.96011.03090.14480.118*
C221.0010 (9)0.8747 (8)0.1451 (7)0.092 (3)
H221.07320.88500.20620.110*
C230.9637 (9)0.7730 (7)0.0928 (7)0.086 (2)
H231.00970.71390.11780.103*
C240.8554 (8)0.7585 (6)0.0011 (6)0.0686 (19)
H240.82990.68900.03470.082*
C250.4477 (7)0.7717 (5)0.1540 (6)0.0568 (16)
C260.4473 (8)0.7694 (6)0.0519 (6)0.072 (2)
H260.52720.78360.00240.086*
C270.3282 (10)0.7461 (7)0.0292 (8)0.089 (2)
H270.32820.74600.04060.107*
C280.2100 (10)0.7233 (7)0.1097 (9)0.090 (3)
H280.13110.70660.09450.108*
C290.2091 (8)0.7251 (6)0.2104 (8)0.084 (2)
H290.12890.71030.26430.101*
C300.3270 (8)0.7491 (6)0.2349 (6)0.071 (2)
H300.32530.75010.30460.086*
C310.983 (2)0.8996 (16)0.4563 (16)0.125 (6)0.50
H31A1.08100.89490.41580.150*0.50
H31B0.92070.95060.40460.150*0.50
C320.946 (3)0.7898 (18)0.488 (2)0.169 (9)0.50
H32A0.88290.77480.55720.253*0.50
H32B1.03220.73410.49370.253*0.50
H32C0.89730.78860.43330.253*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0559 (3)0.0667 (3)0.0645 (4)0.0129 (2)0.0034 (2)0.0317 (3)
N10.060 (3)0.061 (3)0.048 (3)0.009 (3)0.010 (3)0.017 (3)
N20.059 (3)0.069 (4)0.059 (4)0.008 (3)0.001 (3)0.020 (3)
O10.082 (4)0.108 (4)0.098 (5)0.004 (3)0.011 (3)0.044 (4)
O20.159 (8)0.183 (10)0.156 (9)0.016 (8)0.052 (7)0.024 (7)
S10.0633 (11)0.0714 (12)0.0620 (12)0.0065 (9)0.0038 (9)0.0215 (10)
S20.0600 (11)0.0819 (13)0.0612 (12)0.0061 (9)0.0012 (9)0.0257 (10)
C10.056 (4)0.068 (4)0.056 (4)0.007 (3)0.012 (3)0.027 (4)
C20.062 (4)0.057 (4)0.055 (4)0.010 (3)0.010 (3)0.025 (3)
C30.061 (4)0.065 (4)0.060 (5)0.000 (3)0.010 (4)0.012 (4)
C40.049 (4)0.070 (5)0.063 (5)0.009 (3)0.011 (3)0.022 (4)
C50.066 (4)0.057 (4)0.057 (4)0.013 (3)0.001 (3)0.022 (4)
C60.060 (4)0.056 (4)0.057 (4)0.001 (3)0.013 (3)0.018 (3)
C70.055 (4)0.050 (4)0.055 (4)0.002 (3)0.013 (3)0.021 (3)
C80.059 (4)0.067 (5)0.062 (5)0.017 (3)0.008 (4)0.022 (4)
C90.064 (5)0.058 (4)0.065 (5)0.019 (3)0.003 (4)0.025 (4)
C100.044 (4)0.114 (6)0.051 (4)0.007 (4)0.012 (3)0.035 (4)
C110.105 (7)0.089 (6)0.063 (5)0.008 (5)0.023 (5)0.015 (5)
C120.082 (6)0.092 (6)0.070 (6)0.033 (5)0.019 (5)0.040 (5)
C130.050 (4)0.071 (4)0.061 (4)0.012 (3)0.001 (3)0.030 (4)
C140.087 (6)0.092 (6)0.113 (7)0.004 (5)0.036 (5)0.057 (5)
C150.106 (7)0.101 (7)0.175 (11)0.031 (6)0.056 (7)0.087 (8)
C160.112 (8)0.091 (7)0.121 (8)0.001 (6)0.032 (6)0.068 (6)
C170.127 (9)0.118 (8)0.174 (11)0.006 (7)0.065 (8)0.096 (8)
C180.090 (6)0.108 (7)0.165 (9)0.018 (5)0.061 (6)0.085 (7)
C190.049 (4)0.061 (4)0.064 (4)0.007 (3)0.009 (3)0.027 (4)
C200.079 (5)0.070 (5)0.085 (6)0.009 (4)0.002 (4)0.026 (5)
C210.119 (7)0.076 (6)0.081 (6)0.038 (5)0.005 (5)0.005 (5)
C220.095 (6)0.099 (7)0.070 (6)0.022 (5)0.015 (5)0.029 (5)
C230.096 (6)0.081 (6)0.082 (6)0.019 (5)0.008 (5)0.040 (5)
C240.084 (5)0.058 (4)0.069 (5)0.024 (4)0.001 (4)0.028 (4)
C250.051 (4)0.051 (4)0.070 (5)0.003 (3)0.009 (3)0.026 (4)
C260.073 (5)0.070 (5)0.083 (6)0.010 (4)0.014 (4)0.039 (4)
C270.098 (7)0.087 (6)0.101 (7)0.010 (5)0.044 (6)0.040 (5)
C280.085 (6)0.079 (6)0.124 (8)0.018 (5)0.042 (6)0.036 (6)
C290.061 (5)0.075 (5)0.113 (7)0.012 (4)0.022 (5)0.023 (5)
C300.068 (5)0.070 (5)0.076 (5)0.010 (4)0.018 (4)0.022 (4)
C310.103 (8)0.127 (9)0.127 (9)0.007 (7)0.043 (8)0.026 (7)
C320.141 (11)0.189 (12)0.161 (11)0.029 (9)0.043 (8)0.031 (8)
Geometric parameters (Å, º) top
Sn1—C132.129 (7)C14—H140.9300
Sn1—C252.133 (7)C15—C161.351 (12)
Sn1—C192.135 (6)C15—H150.9300
Sn1—S22.460 (2)C16—C171.322 (12)
N1—C11.300 (8)C16—H160.9300
N1—C21.386 (8)C17—C181.387 (12)
N2—C81.257 (8)C17—H170.9300
N2—C51.427 (8)C18—H180.9300
O1—C91.328 (8)C19—C241.366 (9)
O1—C121.405 (9)C19—C201.406 (9)
O2—C311.289 (16)C20—C211.383 (11)
O2—O2i1.42 (3)C20—H200.9300
O2—H20.8200C21—C221.370 (11)
S1—C71.739 (6)C21—H210.9300
S1—C11.740 (7)C22—C231.360 (10)
S2—C11.733 (7)C22—H220.9300
C2—C71.384 (9)C23—C241.396 (10)
C2—C31.403 (9)C23—H230.9300
C3—C41.367 (9)C24—H240.9300
C3—H30.9300C25—C261.372 (9)
C4—C51.405 (9)C25—C301.400 (9)
C4—H40.9300C26—C271.391 (10)
C5—C61.382 (9)C26—H260.9300
C6—C71.386 (9)C27—C281.380 (11)
C6—H60.9300C27—H270.9300
C8—C91.436 (9)C28—C291.350 (12)
C8—H80.9300C28—H280.9300
C9—C101.315 (9)C29—C301.397 (10)
C10—C111.375 (10)C29—H290.9300
C10—H100.9300C30—H300.9300
C11—C121.292 (11)C31—C321.469 (16)
C11—H110.9300C31—H31A0.9700
C12—H120.9300C31—H31B0.9700
C13—C141.341 (10)C32—H32A0.9600
C13—C181.353 (10)C32—H32B0.9600
C14—C151.386 (11)C32—H32C0.9600
C13—Sn1—C25112.7 (2)C17—C16—C15118.2 (9)
C13—Sn1—C19112.6 (2)C17—C16—H16120.9
C25—Sn1—C19109.5 (3)C15—C16—H16120.9
C13—Sn1—S2112.1 (2)C16—C17—C18120.8 (9)
C25—Sn1—S2113.45 (17)C16—C17—H17119.6
C19—Sn1—S295.30 (18)C18—C17—H17119.6
C1—N1—C2109.9 (5)C13—C18—C17121.8 (8)
C8—N2—C5120.7 (6)C13—C18—H18119.1
C9—O1—C12105.5 (6)C17—C18—H18119.1
C31—O2—O2i112 (2)C24—C19—C20118.7 (6)
C31—O2—H2109.6C24—C19—Sn1119.7 (5)
C7—S1—C189.4 (3)C20—C19—Sn1121.5 (5)
C1—S2—Sn195.3 (2)C21—C20—C19119.1 (7)
N1—C1—S2122.9 (5)C21—C20—H20120.4
N1—C1—S1115.8 (5)C19—C20—H20120.4
S2—C1—S1121.3 (4)C22—C21—C20121.0 (8)
C7—C2—N1116.5 (6)C22—C21—H21119.5
C7—C2—C3119.4 (6)C20—C21—H21119.5
N1—C2—C3124.1 (6)C23—C22—C21120.4 (8)
C4—C3—C2118.0 (6)C23—C22—H22119.8
C4—C3—H3121.0C21—C22—H22119.8
C2—C3—H3121.0C22—C23—C24119.3 (7)
C3—C4—C5122.4 (6)C22—C23—H23120.4
C3—C4—H4118.8C24—C23—H23120.4
C5—C4—H4118.8C19—C24—C23121.5 (7)
C6—C5—C4119.5 (6)C19—C24—H24119.3
C6—C5—N2124.5 (6)C23—C24—H24119.3
C4—C5—N2115.9 (6)C26—C25—C30118.9 (7)
C5—C6—C7117.9 (6)C26—C25—Sn1119.0 (5)
C5—C6—H6121.0C30—C25—Sn1122.1 (5)
C7—C6—H6121.0C25—C26—C27120.5 (8)
C2—C7—C6122.7 (6)C25—C26—H26119.8
C2—C7—S1108.4 (5)C27—C26—H26119.8
C6—C7—S1128.9 (5)C28—C27—C26120.3 (8)
N2—C8—C9123.1 (7)C28—C27—H27119.9
N2—C8—H8118.4C26—C27—H27119.9
C9—C8—H8118.4C29—C28—C27119.9 (8)
C10—C9—O1110.5 (6)C29—C28—H28120.1
C10—C9—C8126.3 (7)C27—C28—H28120.1
O1—C9—C8122.9 (7)C28—C29—C30120.9 (8)
C9—C10—C11107.0 (7)C28—C29—H29119.6
C9—C10—H10126.5C30—C29—H29119.6
C11—C10—H10126.5C29—C30—C25119.6 (8)
C12—C11—C10108.8 (7)C29—C30—H30120.2
C12—C11—H11125.6C25—C30—H30120.2
C10—C11—H11125.6O2—C31—C32123.3 (18)
C11—C12—O1108.1 (7)O2—C31—H31A106.5
C11—C12—H12126.0C32—C31—H31A106.5
O1—C12—H12126.0O2—C31—H31B106.5
C14—C13—C18116.7 (7)C32—C31—H31B106.5
C14—C13—Sn1120.0 (6)H31A—C31—H31B106.5
C18—C13—Sn1123.2 (6)C31—C32—H32A109.5
C13—C14—C15121.4 (8)C31—C32—H32B109.5
C13—C14—H14119.3H32A—C32—H32B109.5
C15—C14—H14119.3C31—C32—H32C109.5
C16—C15—C14120.9 (8)H32A—C32—H32C109.5
C16—C15—H15119.5H32B—C32—H32C109.5
C14—C15—H15119.5
Symmetry code: (i) x+2, y+2, z+1.
 

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