Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055560/cv2338sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055560/cv2338Isup2.hkl |
CCDC reference: 664800
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.012 Å
- R factor = 0.051
- wR factor = 0.122
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C3 -C8 1.37 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C15 -C20 1.37 Ang. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12 PLAT414_ALERT_2_C Short Intra D-H..H-X H4 .. H4A .. 1.90 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4A ... ?
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.944 Tmax scaled 0.567 Tmin scaled 0.507 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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
For related literature, see: Dubey & Roy (2003); Gielen (2002); Li et al. (2005). [Reference required for normal values?]
The reaction was carried out under nitrogen atmoshpere. 4-Amino-5-phenyl-4H-1,2,4-triazole-3-thiol (0.192 g, 1 mmol) was added to the solution of benzene (30 ml) with sodium ethoxide (0.68 g, 1 mmol) in a Schlenk flask. After stirring for 10 min, triphenyltin chloride (0.385 g, 1 mmol) was added to the mixture. The mixture was kept at 313 K for 12 h. After cooling down to the room temperature, the solution was filtered. The solvent of the filtrate was gradually removed by evaporation under vacuum until a solid product was obtained. The solid was then recrystallized from diethyl ether. Colourless single crystals of the title complex were obtained after one week. Yield, 87%. Analysis calculated for C26H22N4S1Sn1: C 57.70, H 4.10, N, 10.35; found: C 57.91, H 4.29, N, 10.09. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.
All H atoms were placed in geometrically idealized positions (C—H = 0.93 Å and N—H = 0.86 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2Ueq of the parent atom.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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 (Sheldrick, 1997b).
Fig. 1. The molecular structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms omitted for clarity. |
[Sn(C6H5)3(C8H7N4S)] | Z = 2 |
Mr = 541.23 | F(000) = 544 |
Triclinic, P1 | Dx = 1.511 Mg m−3 |
Hall symbol: -P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.964 (8) Å | Cell parameters from 2210 reflections |
b = 9.656 (8) Å | θ = 2.4–23.8° |
c = 15.481 (13) Å | µ = 1.18 mm−1 |
α = 84.423 (10)° | T = 293 K |
β = 86.911 (10)° | Block, colourless |
γ = 63.110 (8)° | 0.60 × 0.54 × 0.48 mm |
V = 1189.4 (18) Å3 |
Siemens SMART CCD area-detector diffractometer | 4066 independent reflections |
Radiation source: fine-focus sealed tube | 2892 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→10 |
Tmin = 0.537, Tmax = 0.601 | k = −11→11 |
5879 measured reflections | l = −18→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0477P)2] where P = (Fo2 + 2Fc2)/3 |
4066 reflections | (Δ/σ)max = 0.001 |
289 parameters | Δρmax = 1.09 e Å−3 |
1 restraint | Δρmin = −0.92 e Å−3 |
[Sn(C6H5)3(C8H7N4S)] | γ = 63.110 (8)° |
Mr = 541.23 | V = 1189.4 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.964 (8) Å | Mo Kα radiation |
b = 9.656 (8) Å | µ = 1.18 mm−1 |
c = 15.481 (13) Å | T = 293 K |
α = 84.423 (10)° | 0.60 × 0.54 × 0.48 mm |
β = 86.911 (10)° |
Siemens SMART CCD area-detector diffractometer | 4066 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2892 reflections with I > 2σ(I) |
Tmin = 0.537, Tmax = 0.601 | Rint = 0.043 |
5879 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 1 restraint |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.00 | Δρmax = 1.09 e Å−3 |
4066 reflections | Δρmin = −0.92 e Å−3 |
289 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.23422 (6) | 0.73462 (6) | 0.79295 (3) | 0.03700 (19) | |
N1 | 0.1773 (7) | 0.6966 (6) | 0.6698 (3) | 0.0366 (13) | |
N2 | 0.2770 (7) | 0.5565 (6) | 0.6339 (3) | 0.0416 (14) | |
N3 | 0.0812 (7) | 0.7134 (6) | 0.5445 (3) | 0.0364 (13) | |
N4 | −0.0199 (8) | 0.7765 (7) | 0.4711 (3) | 0.0560 (18) | |
H4A | −0.0001 | 0.7230 | 0.4269 | 0.067* | |
H4B | −0.1018 | 0.8687 | 0.4702 | 0.067* | |
S1 | −0.0960 (2) | 0.9684 (2) | 0.63727 (13) | 0.0499 (5) | |
C1 | 0.0562 (8) | 0.7946 (8) | 0.6174 (4) | 0.0348 (16) | |
C2 | 0.2143 (8) | 0.5715 (8) | 0.5573 (4) | 0.0375 (16) | |
C3 | 0.2865 (9) | 0.4439 (8) | 0.4994 (4) | 0.0416 (17) | |
C4 | 0.2067 (10) | 0.4278 (9) | 0.4301 (4) | 0.053 (2) | |
H4 | 0.1001 | 0.5052 | 0.4158 | 0.063* | |
C5 | 0.2786 (12) | 0.3024 (11) | 0.3821 (5) | 0.061 (2) | |
H5 | 0.2230 | 0.2981 | 0.3342 | 0.073* | |
C6 | 0.4307 (13) | 0.1835 (10) | 0.4034 (6) | 0.070 (3) | |
H6 | 0.4776 | 0.0956 | 0.3722 | 0.084* | |
C7 | 0.5135 (12) | 0.1961 (10) | 0.4718 (6) | 0.073 (3) | |
H7 | 0.6190 | 0.1173 | 0.4867 | 0.088* | |
C8 | 0.4400 (11) | 0.3256 (9) | 0.5185 (5) | 0.060 (2) | |
H8 | 0.4978 | 0.3321 | 0.5648 | 0.072* | |
C9 | 0.0375 (8) | 0.7371 (7) | 0.8760 (4) | 0.0331 (15) | |
C10 | −0.0341 (9) | 0.6419 (9) | 0.8663 (5) | 0.053 (2) | |
H10 | −0.0005 | 0.5783 | 0.8205 | 0.064* | |
C11 | −0.1562 (9) | 0.6389 (10) | 0.9236 (6) | 0.066 (2) | |
H11 | −0.2037 | 0.5730 | 0.9163 | 0.079* | |
C12 | −0.2080 (10) | 0.7327 (11) | 0.9915 (6) | 0.068 (2) | |
H12 | −0.2900 | 0.7304 | 1.0303 | 0.082* | |
C13 | −0.1382 (11) | 0.8281 (11) | 1.0009 (5) | 0.070 (3) | |
H13 | −0.1730 | 0.8925 | 1.0463 | 0.084* | |
C14 | −0.0169 (9) | 0.8311 (8) | 0.9445 (4) | 0.0459 (18) | |
H14 | 0.0299 | 0.8974 | 0.9523 | 0.055* | |
C15 | 0.2901 (7) | 0.9268 (7) | 0.7841 (4) | 0.0302 (15) | |
C16 | 0.1941 (9) | 1.0706 (8) | 0.7417 (5) | 0.0481 (19) | |
H16 | 0.0926 | 1.0906 | 0.7178 | 0.058* | |
C17 | 0.2463 (10) | 1.1841 (9) | 0.7344 (5) | 0.061 (2) | |
H17 | 0.1796 | 1.2803 | 0.7056 | 0.073* | |
C18 | 0.3940 (11) | 1.1589 (10) | 0.7684 (5) | 0.064 (2) | |
H18 | 0.4290 | 1.2365 | 0.7629 | 0.077* | |
C19 | 0.4886 (10) | 1.0189 (11) | 0.8105 (6) | 0.064 (2) | |
H19 | 0.5893 | 1.0007 | 0.8345 | 0.077* | |
C20 | 0.4395 (8) | 0.9031 (9) | 0.8184 (5) | 0.0486 (19) | |
H20 | 0.5075 | 0.8074 | 0.8473 | 0.058* | |
C21 | 0.4577 (8) | 0.5244 (7) | 0.8192 (4) | 0.0346 (16) | |
C22 | 0.4786 (9) | 0.4393 (9) | 0.8978 (5) | 0.0482 (19) | |
H22 | 0.3958 | 0.4741 | 0.9404 | 0.058* | |
C23 | 0.6228 (11) | 0.3018 (10) | 0.9135 (6) | 0.071 (3) | |
H23 | 0.6360 | 0.2426 | 0.9662 | 0.085* | |
C24 | 0.7458 (10) | 0.2530 (11) | 0.8516 (7) | 0.075 (3) | |
H24 | 0.8437 | 0.1615 | 0.8626 | 0.089* | |
C25 | 0.7260 (10) | 0.3372 (10) | 0.7739 (6) | 0.068 (2) | |
H25 | 0.8097 | 0.3024 | 0.7317 | 0.081* | |
C26 | 0.5835 (8) | 0.4730 (9) | 0.7575 (5) | 0.051 (2) | |
H26 | 0.5714 | 0.5310 | 0.7044 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0371 (3) | 0.0410 (3) | 0.0347 (3) | −0.0189 (2) | 0.0001 (2) | −0.0043 (2) |
N1 | 0.042 (3) | 0.041 (4) | 0.027 (3) | −0.019 (3) | −0.002 (3) | −0.006 (3) |
N2 | 0.048 (4) | 0.037 (4) | 0.035 (3) | −0.015 (3) | −0.006 (3) | 0.000 (3) |
N3 | 0.045 (4) | 0.040 (4) | 0.027 (3) | −0.022 (3) | −0.009 (3) | 0.004 (3) |
N4 | 0.080 (5) | 0.050 (4) | 0.032 (3) | −0.022 (4) | −0.020 (3) | −0.002 (3) |
S1 | 0.0490 (12) | 0.0419 (12) | 0.0570 (12) | −0.0176 (10) | −0.0044 (9) | −0.0086 (10) |
C1 | 0.042 (4) | 0.041 (4) | 0.031 (4) | −0.028 (4) | 0.000 (3) | 0.001 (3) |
C2 | 0.046 (4) | 0.036 (4) | 0.035 (4) | −0.023 (4) | 0.000 (3) | −0.002 (3) |
C3 | 0.050 (5) | 0.044 (5) | 0.036 (4) | −0.026 (4) | 0.010 (3) | −0.007 (3) |
C4 | 0.067 (5) | 0.067 (6) | 0.043 (5) | −0.046 (5) | 0.010 (4) | −0.014 (4) |
C5 | 0.091 (7) | 0.077 (7) | 0.044 (5) | −0.062 (6) | 0.022 (5) | −0.026 (5) |
C6 | 0.113 (8) | 0.053 (6) | 0.059 (6) | −0.050 (6) | 0.036 (6) | −0.028 (5) |
C7 | 0.081 (6) | 0.053 (6) | 0.069 (6) | −0.014 (5) | 0.014 (5) | −0.021 (5) |
C8 | 0.076 (6) | 0.057 (6) | 0.051 (5) | −0.031 (5) | 0.007 (4) | −0.017 (4) |
C9 | 0.037 (4) | 0.031 (4) | 0.029 (4) | −0.014 (3) | −0.009 (3) | 0.004 (3) |
C10 | 0.044 (5) | 0.063 (5) | 0.061 (5) | −0.031 (4) | 0.004 (4) | −0.012 (4) |
C11 | 0.047 (5) | 0.078 (7) | 0.091 (7) | −0.047 (5) | 0.001 (5) | 0.004 (5) |
C12 | 0.051 (5) | 0.083 (7) | 0.073 (6) | −0.036 (5) | 0.016 (5) | 0.004 (5) |
C13 | 0.066 (6) | 0.083 (7) | 0.056 (6) | −0.029 (5) | 0.027 (5) | −0.022 (5) |
C14 | 0.047 (5) | 0.049 (5) | 0.047 (5) | −0.026 (4) | 0.008 (4) | −0.011 (4) |
C15 | 0.025 (3) | 0.037 (4) | 0.030 (4) | −0.014 (3) | 0.007 (3) | −0.012 (3) |
C16 | 0.042 (4) | 0.045 (5) | 0.059 (5) | −0.019 (4) | −0.015 (4) | −0.004 (4) |
C17 | 0.075 (6) | 0.043 (5) | 0.070 (6) | −0.032 (5) | −0.016 (5) | 0.007 (4) |
C18 | 0.087 (7) | 0.065 (6) | 0.066 (6) | −0.055 (6) | −0.004 (5) | −0.009 (5) |
C19 | 0.050 (5) | 0.076 (7) | 0.081 (6) | −0.039 (5) | −0.014 (5) | −0.012 (5) |
C20 | 0.041 (4) | 0.049 (5) | 0.061 (5) | −0.024 (4) | −0.012 (4) | −0.002 (4) |
C21 | 0.031 (4) | 0.033 (4) | 0.043 (4) | −0.018 (3) | −0.003 (3) | −0.004 (3) |
C22 | 0.042 (4) | 0.059 (5) | 0.036 (4) | −0.016 (4) | −0.004 (3) | 0.003 (4) |
C23 | 0.076 (7) | 0.069 (6) | 0.052 (5) | −0.023 (5) | −0.024 (5) | 0.024 (5) |
C24 | 0.042 (5) | 0.069 (6) | 0.084 (7) | −0.001 (5) | −0.014 (5) | 0.006 (6) |
C25 | 0.043 (5) | 0.063 (6) | 0.072 (6) | −0.005 (4) | 0.004 (4) | 0.003 (5) |
C26 | 0.035 (4) | 0.051 (5) | 0.054 (5) | −0.011 (4) | 0.007 (4) | 0.007 (4) |
Sn1—N1 | 2.107 (5) | C11—C12 | 1.375 (11) |
Sn1—C9 | 2.119 (6) | C11—H11 | 0.9300 |
Sn1—C15 | 2.120 (6) | C12—C13 | 1.349 (11) |
Sn1—C21 | 2.133 (6) | C12—H12 | 0.9300 |
N1—C1 | 1.322 (8) | C13—C14 | 1.366 (10) |
N1—N2 | 1.391 (7) | C13—H13 | 0.9300 |
N2—C2 | 1.307 (8) | C14—H14 | 0.9300 |
N3—C2 | 1.354 (8) | C15—C16 | 1.379 (9) |
N3—C1 | 1.387 (7) | C15—C20 | 1.380 (9) |
N3—N4 | 1.401 (7) | C16—C17 | 1.366 (10) |
N4—H4A | 0.860 | C16—H16 | 0.9300 |
N4—H4B | 0.860 | C17—C18 | 1.360 (11) |
S1—C1 | 1.660 (7) | C17—H17 | 0.9300 |
C2—C3 | 1.474 (9) | C18—C19 | 1.350 (11) |
C3—C8 | 1.357 (10) | C18—H18 | 0.9300 |
C3—C4 | 1.379 (9) | C19—C20 | 1.368 (10) |
C4—C5 | 1.360 (9) | C19—H19 | 0.9300 |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.358 (12) | C21—C22 | 1.371 (9) |
C5—H5 | 0.9300 | C21—C26 | 1.379 (9) |
C6—C7 | 1.371 (11) | C22—C23 | 1.383 (10) |
C6—H6 | 0.9300 | C22—H22 | 0.9300 |
C7—C8 | 1.378 (10) | C23—C24 | 1.364 (11) |
C7—H7 | 0.9300 | C23—H23 | 0.9300 |
C8—H8 | 0.9300 | C24—C25 | 1.356 (12) |
C9—C10 | 1.360 (9) | C24—H24 | 0.9300 |
C9—C14 | 1.384 (8) | C25—C26 | 1.369 (10) |
C10—C11 | 1.381 (10) | C25—H25 | 0.9300 |
C10—H10 | 0.9300 | C26—H26 | 0.9300 |
N1—Sn1—C9 | 105.3 (2) | C12—C11—H11 | 119.7 |
N1—Sn1—C15 | 110.6 (2) | C10—C11—H11 | 119.7 |
C9—Sn1—C15 | 119.5 (2) | C13—C12—C11 | 118.9 (7) |
N1—Sn1—C21 | 99.9 (2) | C13—C12—H12 | 120.5 |
C9—Sn1—C21 | 110.3 (3) | C11—C12—H12 | 120.5 |
C15—Sn1—C21 | 109.4 (2) | C12—C13—C14 | 120.8 (8) |
C1—N1—N2 | 112.5 (5) | C12—C13—H13 | 119.6 |
C1—N1—Sn1 | 127.6 (4) | C14—C13—H13 | 119.6 |
N2—N1—Sn1 | 119.8 (4) | C13—C14—C9 | 121.2 (7) |
C2—N2—N1 | 105.0 (5) | C13—C14—H14 | 119.4 |
C2—N3—C1 | 109.3 (5) | C9—C14—H14 | 119.4 |
C2—N3—N4 | 128.1 (5) | C16—C15—C20 | 117.3 (6) |
C1—N3—N4 | 122.5 (6) | C16—C15—Sn1 | 125.1 (4) |
N3—N4—H4A | 120.0 | C20—C15—Sn1 | 117.4 (5) |
N3—N4—H4B | 120.0 | C17—C16—C15 | 120.8 (6) |
H4A—N4—H4B | 120.0 | C17—C16—H16 | 119.6 |
N1—C1—N3 | 103.4 (6) | C15—C16—H16 | 119.6 |
N1—C1—S1 | 127.9 (5) | C18—C17—C16 | 121.2 (8) |
N3—C1—S1 | 128.6 (5) | C18—C17—H17 | 119.4 |
N2—C2—N3 | 109.8 (5) | C16—C17—H17 | 119.4 |
N2—C2—C3 | 121.0 (6) | C19—C18—C17 | 118.5 (7) |
N3—C2—C3 | 129.2 (6) | C19—C18—H18 | 120.7 |
C8—C3—C4 | 116.2 (7) | C17—C18—H18 | 120.7 |
C8—C3—C2 | 118.0 (6) | C18—C19—C20 | 121.4 (7) |
C4—C3—C2 | 125.6 (7) | C18—C19—H19 | 119.3 |
C5—C4—C3 | 122.2 (8) | C20—C19—H19 | 119.3 |
C5—C4—H4 | 118.9 | C19—C20—C15 | 120.7 (7) |
C3—C4—H4 | 118.9 | C19—C20—H20 | 119.6 |
C6—C5—C4 | 120.7 (8) | C15—C20—H20 | 119.6 |
C6—C5—H5 | 119.6 | C22—C21—C26 | 119.2 (6) |
C4—C5—H5 | 119.6 | C22—C21—Sn1 | 120.5 (5) |
C5—C6—C7 | 118.5 (7) | C26—C21—Sn1 | 120.3 (5) |
C5—C6—H6 | 120.8 | C21—C22—C23 | 120.0 (7) |
C7—C6—H6 | 120.8 | C21—C22—H22 | 120.0 |
C6—C7—C8 | 119.9 (9) | C23—C22—H22 | 120.0 |
C6—C7—H7 | 120.1 | C24—C23—C22 | 119.9 (8) |
C8—C7—H7 | 120.1 | C24—C23—H23 | 120.1 |
C3—C8—C7 | 122.5 (8) | C22—C23—H23 | 120.1 |
C3—C8—H8 | 118.8 | C25—C24—C23 | 120.3 (8) |
C7—C8—H8 | 118.8 | C25—C24—H24 | 119.8 |
C10—C9—C14 | 117.9 (6) | C23—C24—H24 | 119.8 |
C10—C9—Sn1 | 121.3 (5) | C24—C25—C26 | 120.3 (8) |
C14—C9—Sn1 | 120.7 (5) | C24—C25—H25 | 119.8 |
C9—C10—C11 | 120.7 (7) | C26—C25—H25 | 119.8 |
C9—C10—H10 | 119.7 | C25—C26—C21 | 120.2 (7) |
C11—C10—H10 | 119.7 | C25—C26—H26 | 119.9 |
C12—C11—C10 | 120.5 (7) | C21—C26—H26 | 119.9 |
C9—Sn1—N1—C1 | 71.0 (6) | C15—Sn1—C9—C14 | −21.9 (6) |
C15—Sn1—N1—C1 | −59.4 (6) | C21—Sn1—C9—C14 | 106.2 (6) |
C21—Sn1—N1—C1 | −174.6 (5) | C14—C9—C10—C11 | −0.5 (11) |
C9—Sn1—N1—N2 | −111.5 (5) | Sn1—C9—C10—C11 | 176.6 (6) |
C15—Sn1—N1—N2 | 118.1 (5) | C9—C10—C11—C12 | 0.3 (12) |
C21—Sn1—N1—N2 | 2.9 (5) | C10—C11—C12—C13 | 0.3 (13) |
C1—N1—N2—C2 | 0.4 (7) | C11—C12—C13—C14 | −0.5 (14) |
Sn1—N1—N2—C2 | −177.5 (4) | C12—C13—C14—C9 | 0.2 (13) |
N2—N1—C1—N3 | −0.5 (7) | C10—C9—C14—C13 | 0.3 (11) |
Sn1—N1—C1—N3 | 177.1 (4) | Sn1—C9—C14—C13 | −176.9 (6) |
N2—N1—C1—S1 | 175.9 (5) | N1—Sn1—C15—C16 | 48.9 (6) |
Sn1—N1—C1—S1 | −6.4 (9) | C9—Sn1—C15—C16 | −73.5 (6) |
C2—N3—C1—N1 | 0.5 (7) | C21—Sn1—C15—C16 | 158.0 (5) |
N4—N3—C1—N1 | −179.0 (5) | N1—Sn1—C15—C20 | −126.6 (5) |
C2—N3—C1—S1 | −176.0 (5) | C9—Sn1—C15—C20 | 111.0 (5) |
N4—N3—C1—S1 | 4.5 (9) | C21—Sn1—C15—C20 | −17.5 (6) |
N1—N2—C2—N3 | −0.1 (7) | C20—C15—C16—C17 | 0.1 (10) |
N1—N2—C2—C3 | −179.2 (6) | Sn1—C15—C16—C17 | −175.5 (5) |
C1—N3—C2—N2 | −0.2 (7) | C15—C16—C17—C18 | 0.0 (12) |
N4—N3—C2—N2 | 179.3 (6) | C16—C17—C18—C19 | −0.4 (13) |
C1—N3—C2—C3 | 178.8 (6) | C17—C18—C19—C20 | 0.6 (13) |
N4—N3—C2—C3 | −1.7 (11) | C18—C19—C20—C15 | −0.5 (12) |
N2—C2—C3—C8 | −14.5 (10) | C16—C15—C20—C19 | 0.2 (10) |
N3—C2—C3—C8 | 166.6 (7) | Sn1—C15—C20—C19 | 176.0 (5) |
N2—C2—C3—C4 | 160.5 (7) | N1—Sn1—C21—C22 | −132.2 (5) |
N3—C2—C3—C4 | −18.4 (11) | C9—Sn1—C21—C22 | −21.7 (6) |
C8—C3—C4—C5 | −1.5 (11) | C15—Sn1—C21—C22 | 111.7 (5) |
C2—C3—C4—C5 | −176.6 (7) | N1—Sn1—C21—C26 | 48.3 (6) |
C3—C4—C5—C6 | 3.0 (12) | C9—Sn1—C21—C26 | 158.8 (5) |
C4—C5—C6—C7 | −3.0 (13) | C15—Sn1—C21—C26 | −67.8 (6) |
C5—C6—C7—C8 | 1.6 (13) | C26—C21—C22—C23 | −1.6 (10) |
C4—C3—C8—C7 | 0.1 (12) | Sn1—C21—C22—C23 | 178.9 (6) |
C2—C3—C8—C7 | 175.6 (7) | C21—C22—C23—C24 | 1.6 (12) |
C6—C7—C8—C3 | −0.1 (14) | C22—C23—C24—C25 | −1.2 (14) |
N1—Sn1—C9—C10 | 36.1 (6) | C23—C24—C25—C26 | 0.9 (14) |
C15—Sn1—C9—C10 | 161.1 (5) | C24—C25—C26—C21 | −0.9 (12) |
C21—Sn1—C9—C10 | −70.9 (6) | C22—C21—C26—C25 | 1.3 (10) |
N1—Sn1—C9—C14 | −146.9 (5) | Sn1—C21—C26—C25 | −179.2 (6) |
Experimental details
Crystal data | |
Chemical formula | [Sn(C6H5)3(C8H7N4S)] |
Mr | 541.23 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.964 (8), 9.656 (8), 15.481 (13) |
α, β, γ (°) | 84.423 (10), 86.911 (10), 63.110 (8) |
V (Å3) | 1189.4 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.18 |
Crystal size (mm) | 0.60 × 0.54 × 0.48 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.537, 0.601 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5879, 4066, 2892 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.122, 1.00 |
No. of reflections | 4066 |
No. of parameters | 289 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.09, −0.92 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
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In recent years, organotin complexes have been attracting more and more attention for their wide industrial applications and biological activities (Dubey & Roy, 2003). In order to explore the relationships between the properties and structures, a large number of organotin complexes have been prepared (Gielen, 2002). We report here the structure of the title mononuclear Sn(IV) complex, (I).
The molecular structure of complex (I) is shown in Fig. 1. Sn1 is four-coordinated in a distorted tetrahedron geometry. The Sn—N bond distance is comparable to that found in [phenyl-tris(pyrimidine-2-thiolato)tin(IV)] (Li et al., 2005). The bond angles at the Sn1 atom range from 99.9 (2) to 110.7 (2)°. The crystal packing exhibits no classical intermolecular hydrogen bonds.