Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300583X/lh6044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680300583X/lh6044Isup2.hkl |
CCDC reference: 209890
Key indicators
- Single-crystal X-ray study
- T = 158 K
- Mean (C-C) = 0.004 Å
- R factor = 0.027
- wR factor = 0.062
- Data-to-parameter ratio = 15.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was prepared by heating triphenyltin trifluoroacetate (0.73 g, 2 mmol), which was synthesized from triphenyltin hydroxide and trifluoroacetic acid, with an equimolar quantity of terpyridine (0.47 g, 2 mmol) in ethanol. The product was obtained as crystals upon evaporation of the solvent (m.p. 409–410 K).
The carbon-bound H atoms were positioned geometrically and were allowed to ride on their parent C atoms, with Uiso(H) = 1.2Ueq(C). The water H atoms were located and refined, subject to O—H = 0.85±0.01 Å.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Fig. 1. ORTEPII (Johnson, 1976) plot of (I), with ellipsoids at the 50% probability level. H atoms are drawn as spheres of arbitrary radii. |
[Sn(C2F3O2)(C6H5)3(H2O)]·C15H11N3 | F(000) = 1440 |
Mr = 714.29 | Dx = 1.512 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6202 reflections |
a = 10.4257 (7) Å | θ = 2.0–26.4° |
b = 10.0510 (7) Å | µ = 0.87 mm−1 |
c = 30.025 (2) Å | T = 158 K |
β = 94.265 (1)° | Plate, colorless |
V = 3137.6 (4) Å3 | 0.50 × 0.24 × 0.15 mm |
Z = 4 |
Bruker SMART area-detector diffractometer | 6320 independent reflections |
Radiation source: fine-focus sealed tube | 5021 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ω scans | θmax = 26.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→6 |
Tmin = 0.744, Tmax = 0.877 | k = −12→12 |
39984 measured reflections | l = −37→37 |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0356P)2] where P = (Fo2 + 2Fc2)/3 |
6320 reflections | (Δ/σ)max = 0.001 |
414 parameters | Δρmax = 0.50 e Å−3 |
2 restraints | Δρmin = −0.43 e Å−3 |
[Sn(C2F3O2)(C6H5)3(H2O)]·C15H11N3 | V = 3137.6 (4) Å3 |
Mr = 714.29 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.4257 (7) Å | µ = 0.87 mm−1 |
b = 10.0510 (7) Å | T = 158 K |
c = 30.025 (2) Å | 0.50 × 0.24 × 0.15 mm |
β = 94.265 (1)° |
Bruker SMART area-detector diffractometer | 6320 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5021 reflections with I > 2σ(I) |
Tmin = 0.744, Tmax = 0.877 | Rint = 0.051 |
39984 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 2 restraints |
wR(F2) = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.50 e Å−3 |
6320 reflections | Δρmin = −0.43 e Å−3 |
414 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.34215 (1) | 0.65441 (2) | 0.37274 (1) | 0.0243 (1) | |
F1 | 0.0065 (2) | 0.8301 (2) | 0.4617 (1) | 0.0683 (5) | |
F2 | 0.1695 (2) | 0.9420 (2) | 0.4864 (1) | 0.0645 (5) | |
F3 | 0.0339 (2) | 1.0293 (2) | 0.4384 (1) | 0.0830 (6) | |
O1 | 0.2095 (2) | 0.7439 (2) | 0.4190 (1) | 0.034 (1) | |
O2 | 0.1917 (2) | 0.9364 (2) | 0.3810 (1) | 0.040 (1) | |
O1w | 0.4810 (2) | 0.5434 (2) | 0.3311 (1) | 0.029 (1) | |
N1 | 0.5289 (2) | 0.6492 (2) | 0.2488 (1) | 0.030 (1) | |
N2 | 0.7394 (2) | 0.6247 (2) | 0.3091 (1) | 0.029 (1) | |
N3 | 0.7033 (2) | 0.4772 (2) | 0.3845 (1) | 0.033 (1) | |
C1 | 0.4784 (2) | 0.8095 (2) | 0.3868 (1) | 0.029 (1) | |
C2 | 0.4993 (3) | 0.8628 (3) | 0.4295 (1) | 0.045 (1) | |
C3 | 0.5872 (3) | 0.9663 (3) | 0.4376 (1) | 0.055 (1) | |
C4 | 0.6536 (3) | 1.0159 (3) | 0.4033 (1) | 0.053 (1) | |
C5 | 0.6309 (2) | 0.9667 (3) | 0.3607 (1) | 0.046 (1) | |
C6 | 0.5434 (2) | 0.8630 (2) | 0.3527 (1) | 0.035 (1) | |
C7 | 0.2202 (2) | 0.6654 (2) | 0.3129 (1) | 0.027 (1) | |
C8 | 0.1465 (2) | 0.5549 (2) | 0.2983 (1) | 0.035 (1) | |
C9 | 0.0739 (2) | 0.5575 (3) | 0.2577 (1) | 0.043 (1) | |
C10 | 0.0740 (2) | 0.6695 (3) | 0.2307 (1) | 0.043 (1) | |
C11 | 0.1446 (2) | 0.7797 (3) | 0.2448 (1) | 0.037 (1) | |
C12 | 0.2170 (2) | 0.7780 (2) | 0.2855 (1) | 0.029 (1) | |
C13 | 0.3357 (2) | 0.4767 (2) | 0.4109 (1) | 0.031 (1) | |
C14 | 0.3269 (3) | 0.4804 (3) | 0.4569 (1) | 0.061 (1) | |
C15 | 0.3232 (4) | 0.3644 (4) | 0.4815 (1) | 0.085 (1) | |
C16 | 0.3275 (4) | 0.2427 (3) | 0.4608 (1) | 0.071 (1) | |
C17 | 0.3372 (3) | 0.2355 (3) | 0.4155 (1) | 0.053 (1) | |
C18 | 0.3414 (2) | 0.3516 (2) | 0.3907 (1) | 0.039 (1) | |
C19 | 0.1727 (2) | 0.8637 (2) | 0.4120 (1) | 0.031 (1) | |
C20 | 0.0938 (3) | 0.9171 (3) | 0.4497 (1) | 0.042 (1) | |
C21 | 0.4353 (2) | 0.6382 (2) | 0.2160 (1) | 0.036 (1) | |
C22 | 0.4498 (3) | 0.6776 (2) | 0.1722 (1) | 0.046 (1) | |
C23 | 0.5664 (3) | 0.7291 (3) | 0.1621 (1) | 0.050 (1) | |
C24 | 0.6622 (3) | 0.7427 (3) | 0.1954 (1) | 0.042 (1) | |
C25 | 0.6417 (2) | 0.7019 (2) | 0.2387 (1) | 0.030 (1) | |
C26 | 0.7404 (2) | 0.7167 (2) | 0.2763 (1) | 0.031 (1) | |
C27 | 0.8264 (2) | 0.8232 (2) | 0.2781 (1) | 0.039 (1) | |
C28 | 0.9110 (2) | 0.8355 (3) | 0.3151 (1) | 0.045 (1) | |
C29 | 0.9094 (2) | 0.7435 (3) | 0.3488 (1) | 0.042 (1) | |
C30 | 0.8221 (2) | 0.6387 (2) | 0.3450 (1) | 0.032 (1) | |
C31 | 0.8168 (2) | 0.5392 (2) | 0.3813 (1) | 0.033 (1) | |
C32 | 0.9223 (3) | 0.5118 (3) | 0.4110 (1) | 0.044 (1) | |
C33 | 0.9114 (3) | 0.4189 (3) | 0.4445 (1) | 0.051 (1) | |
C34 | 0.7965 (3) | 0.3565 (3) | 0.4479 (1) | 0.050 (1) | |
C35 | 0.6949 (3) | 0.3884 (3) | 0.4175 (1) | 0.043 (1) | |
H1w1 | 0.500 (3) | 0.582 (3) | 0.3075 (6) | 0.06 (1)* | |
H1w2 | 0.552 (2) | 0.527 (3) | 0.3456 (8) | 0.06 (1)* | |
H2 | 0.4535 | 0.8286 | 0.4532 | 0.054* | |
H3 | 0.6013 | 1.0025 | 0.4668 | 0.066* | |
H4 | 0.7153 | 1.0844 | 0.4091 | 0.063* | |
H5 | 0.6746 | 1.0032 | 0.3369 | 0.055* | |
H6 | 0.5284 | 0.8288 | 0.3232 | 0.041* | |
H8 | 0.1464 | 0.4775 | 0.3164 | 0.042* | |
H9 | 0.0239 | 0.4822 | 0.2483 | 0.052* | |
H10 | 0.0257 | 0.6703 | 0.2027 | 0.052* | |
H11 | 0.1436 | 0.8570 | 0.2266 | 0.044* | |
H12 | 0.2652 | 0.8546 | 0.2949 | 0.035* | |
H14 | 0.3235 | 0.5639 | 0.4716 | 0.073* | |
H15 | 0.3177 | 0.3688 | 0.5129 | 0.102* | |
H16 | 0.3238 | 0.1634 | 0.4778 | 0.086* | |
H17 | 0.3409 | 0.1514 | 0.4013 | 0.063* | |
H18 | 0.3484 | 0.3461 | 0.3594 | 0.047* | |
H21 | 0.3551 | 0.6018 | 0.2230 | 0.043* | |
H22 | 0.3809 | 0.6691 | 0.1499 | 0.055* | |
H23 | 0.5800 | 0.7550 | 0.1324 | 0.060* | |
H24 | 0.7426 | 0.7798 | 0.1890 | 0.051* | |
H27 | 0.8263 | 0.8856 | 0.2543 | 0.047* | |
H28 | 0.9705 | 0.9072 | 0.3173 | 0.054* | |
H29 | 0.9674 | 0.7514 | 0.3746 | 0.050* | |
H32 | 1.0015 | 0.5567 | 0.4083 | 0.052* | |
H33 | 0.9829 | 0.3989 | 0.4649 | 0.061* | |
H34 | 0.7863 | 0.2925 | 0.4706 | 0.059* | |
H35 | 0.6148 | 0.3450 | 0.4201 | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02413 (9) | 0.02435 (8) | 0.02434 (9) | −0.00214 (7) | 0.00159 (6) | 0.00168 (7) |
F1 | 0.056 (1) | 0.082 (1) | 0.072 (1) | −0.015 (1) | 0.035 (1) | −0.025 (1) |
F2 | 0.075 (1) | 0.080 (1) | 0.038 (1) | −0.005 (1) | −0.002 (1) | −0.023 (1) |
F3 | 0.102 (2) | 0.078 (1) | 0.072 (1) | 0.054 (1) | 0.025 (1) | 0.004 (1) |
O1 | 0.034 (1) | 0.032 (1) | 0.036 (1) | 0.002 (1) | 0.008 (1) | −0.001 (1) |
O2 | 0.045 (1) | 0.036 (1) | 0.040 (1) | 0.002 (1) | 0.003 (1) | 0.003 (1) |
O1w | 0.024 (1) | 0.033 (1) | 0.029 (1) | 0.000 (1) | 0.003 (1) | 0.003 (1) |
N1 | 0.031 (1) | 0.030 (1) | 0.028 (1) | 0.002 (1) | 0.004 (1) | −0.004 (1) |
N2 | 0.024 (1) | 0.029 (1) | 0.034 (1) | −0.001 (1) | 0.004 (1) | −0.001 (1) |
N3 | 0.033 (1) | 0.034 (1) | 0.032 (1) | 0.002 (1) | −0.001 (1) | 0.001 (1) |
C1 | 0.025 (1) | 0.025 (1) | 0.035 (1) | −0.002 (1) | −0.001 (1) | 0.001 (1) |
C2 | 0.048 (2) | 0.049 (2) | 0.037 (2) | −0.010 (1) | −0.008 (1) | 0.004 (1) |
C3 | 0.063 (2) | 0.048 (2) | 0.051 (2) | −0.012 (2) | −0.017 (2) | −0.010 (2) |
C4 | 0.040 (2) | 0.035 (2) | 0.081 (2) | −0.013 (1) | −0.010 (2) | −0.004 (2) |
C5 | 0.035 (2) | 0.032 (1) | 0.072 (2) | −0.005 (1) | 0.014 (1) | 0.002 (1) |
C6 | 0.034 (1) | 0.030 (1) | 0.041 (2) | −0.002 (1) | 0.007 (1) | −0.003 (1) |
C7 | 0.024 (1) | 0.028 (1) | 0.030 (1) | 0.001 (1) | 0.003 (1) | −0.002 (1) |
C8 | 0.032 (1) | 0.031 (1) | 0.042 (2) | −0.001 (1) | 0.001 (1) | −0.001 (1) |
C9 | 0.037 (2) | 0.045 (2) | 0.047 (2) | −0.003 (1) | −0.009 (1) | −0.014 (1) |
C10 | 0.036 (2) | 0.059 (2) | 0.034 (1) | 0.008 (1) | −0.008 (1) | −0.009 (1) |
C11 | 0.034 (1) | 0.045 (2) | 0.030 (1) | 0.008 (1) | 0.001 (1) | 0.005 (1) |
C12 | 0.026 (1) | 0.032 (1) | 0.031 (1) | −0.001 (1) | 0.004 (1) | 0.000 (1) |
C13 | 0.027 (1) | 0.031 (1) | 0.034 (1) | −0.002 (1) | 0.002 (1) | 0.007 (1) |
C14 | 0.099 (3) | 0.043 (2) | 0.042 (2) | 0.009 (2) | 0.018 (2) | 0.011 (1) |
C15 | 0.147 (4) | 0.065 (3) | 0.044 (2) | 0.005 (2) | 0.016 (2) | 0.026 (2) |
C16 | 0.101 (3) | 0.048 (2) | 0.063 (2) | −0.013 (2) | −0.006 (2) | 0.032 (2) |
C17 | 0.060 (2) | 0.030 (2) | 0.064 (2) | −0.009 (1) | −0.018 (2) | 0.009 (1) |
C18 | 0.042 (2) | 0.034 (1) | 0.039 (1) | −0.008 (1) | −0.007 (1) | 0.006 (1) |
C19 | 0.025 (1) | 0.037 (2) | 0.032 (1) | −0.003 (1) | −0.003 (1) | −0.005 (1) |
C20 | 0.044 (2) | 0.043 (2) | 0.039 (2) | 0.007 (1) | 0.003 (1) | −0.008 (1) |
C21 | 0.038 (1) | 0.032 (1) | 0.037 (1) | 0.006 (1) | −0.003 (1) | −0.008 (1) |
C22 | 0.066 (2) | 0.032 (2) | 0.036 (2) | 0.013 (1) | −0.015 (1) | −0.005 (1) |
C23 | 0.077 (2) | 0.038 (2) | 0.034 (2) | 0.003 (2) | 0.008 (2) | 0.009 (1) |
C24 | 0.050 (2) | 0.038 (2) | 0.040 (2) | 0.001 (1) | 0.012 (1) | 0.010 (1) |
C25 | 0.036 (1) | 0.022 (1) | 0.033 (1) | 0.002 (1) | 0.009 (1) | 0.000 (1) |
C26 | 0.026 (1) | 0.030 (1) | 0.036 (1) | 0.001 (1) | 0.010 (1) | −0.001 (1) |
C27 | 0.034 (1) | 0.031 (1) | 0.054 (2) | −0.004 (1) | 0.016 (1) | 0.002 (1) |
C28 | 0.030 (1) | 0.038 (2) | 0.068 (2) | −0.012 (1) | 0.010 (1) | −0.009 (2) |
C29 | 0.026 (1) | 0.041 (2) | 0.057 (2) | −0.006 (1) | −0.003 (1) | −0.010 (1) |
C30 | 0.023 (1) | 0.033 (1) | 0.040 (1) | 0.001 (1) | 0.001 (1) | −0.005 (1) |
C31 | 0.034 (1) | 0.032 (1) | 0.031 (1) | 0.003 (1) | −0.002 (1) | −0.009 (1) |
C32 | 0.042 (2) | 0.045 (2) | 0.042 (2) | 0.002 (1) | −0.011 (1) | −0.010 (1) |
C33 | 0.056 (2) | 0.055 (2) | 0.039 (2) | 0.010 (2) | −0.018 (1) | −0.010 (1) |
C34 | 0.071 (2) | 0.047 (2) | 0.030 (1) | 0.011 (2) | −0.003 (1) | 0.002 (1) |
C35 | 0.050 (2) | 0.044 (2) | 0.036 (2) | 0.001 (1) | 0.004 (1) | 0.004 (1) |
Sn1—C1 | 2.130 (2) | C25—C26 | 1.478 (3) |
Sn1—C7 | 2.126 (2) | C26—C27 | 1.395 (3) |
Sn1—C13 | 2.126 (2) | C27—C28 | 1.372 (4) |
Sn1—O1 | 2.221 (2) | C28—C29 | 1.373 (4) |
Sn1—O1w | 2.274 (2) | C29—C30 | 1.391 (3) |
F1—C20 | 1.330 (3) | C30—C31 | 1.486 (3) |
F2—C20 | 1.331 (3) | C31—C32 | 1.391 (3) |
F3—C20 | 1.321 (3) | C32—C33 | 1.384 (4) |
O1—C19 | 1.276 (3) | C33—C34 | 1.363 (4) |
O2—C19 | 1.211 (3) | C34—C35 | 1.384 (4) |
N1—C21 | 1.337 (3) | O1w—H1w1 | 0.84 (1) |
N1—C25 | 1.345 (3) | O1w—H1w2 | 0.84 (1) |
N2—C30 | 1.336 (3) | C2—H2 | 0.95 |
N2—C26 | 1.352 (3) | C3—H3 | 0.95 |
N3—C35 | 1.341 (3) | C4—H4 | 0.95 |
N3—C31 | 1.347 (3) | C5—H5 | 0.95 |
C1—C6 | 1.379 (3) | C6—H6 | 0.95 |
C1—C2 | 1.393 (4) | C8—H8 | 0.95 |
C2—C3 | 1.397 (4) | C9—H9 | 0.95 |
C3—C4 | 1.376 (4) | C10—H10 | 0.95 |
C4—C5 | 1.374 (4) | C11—H11 | 0.95 |
C5—C6 | 1.394 (3) | C12—H12 | 0.95 |
C7—C12 | 1.398 (3) | C14—H14 | 0.95 |
C7—C8 | 1.402 (3) | C15—H15 | 0.95 |
C8—C9 | 1.387 (3) | C16—H16 | 0.95 |
C9—C10 | 1.386 (4) | C17—H17 | 0.95 |
C10—C11 | 1.378 (4) | C18—H18 | 0.95 |
C11—C12 | 1.387 (3) | C21—H21 | 0.95 |
C13—C14 | 1.391 (4) | C22—H22 | 0.95 |
C13—C18 | 1.399 (3) | C23—H23 | 0.95 |
C14—C15 | 1.383 (4) | C24—H24 | 0.95 |
C15—C16 | 1.374 (5) | C27—H27 | 0.95 |
C16—C17 | 1.372 (4) | C28—H28 | 0.95 |
C17—C18 | 1.387 (4) | C29—H29 | 0.95 |
C19—C20 | 1.546 (3) | C32—H32 | 0.95 |
C21—C22 | 1.392 (4) | C33—H33 | 0.95 |
C22—C23 | 1.376 (4) | C34—H34 | 0.95 |
C23—C24 | 1.366 (4) | C35—H35 | 0.95 |
C24—C25 | 1.394 (3) | ||
C1—Sn1—C7 | 118.5 (1) | N3—C31—C32 | 121.4 (2) |
C1—Sn1—C13 | 123.8 (1) | N3—C31—C30 | 116.4 (2) |
C1—Sn1—O1 | 91.0 (1) | C32—C31—C30 | 122.2 (2) |
C1—Sn1—O1w | 91.4 (1) | C33—C32—C31 | 119.7 (3) |
C7—Sn1—C13 | 117.3 (1) | C34—C33—C32 | 119.0 (3) |
C7—Sn1—O1 | 98.4 (1) | C33—C34—C35 | 118.6 (3) |
C7—Sn1—O1w | 85.8 (1) | N3—C35—C34 | 123.5 (3) |
C13—Sn1—O1 | 87.5 (1) | Sn1—O1w—H1w1 | 116 (2) |
C13—Sn1—O1w | 86.0 (1) | Sn1—O1w—H1w2 | 112 (2) |
O1—Sn1—O1w | 173.4 (1) | H1w1—O1w—H1w2 | 106 (3) |
C19—O1—Sn1 | 118.2 (2) | C1—C2—H2 | 119.9 |
C21—N1—C25 | 118.0 (2) | C3—C2—H2 | 119.9 |
C30—N2—C26 | 118.4 (2) | C4—C3—H3 | 120.0 |
C35—N3—C31 | 117.8 (2) | C2—C3—H3 | 120.0 |
C6—C1—C2 | 118.9 (2) | C5—C4—H4 | 119.8 |
C6—C1—Sn1 | 119.7 (2) | C3—C4—H4 | 119.8 |
C2—C1—Sn1 | 121.3 (2) | C4—C5—H5 | 120.1 |
C1—C2—C3 | 120.2 (3) | C6—C5—H5 | 120.1 |
C4—C3—C2 | 119.9 (3) | C1—C6—H6 | 119.6 |
C5—C4—C3 | 120.3 (2) | C5—C6—H6 | 119.6 |
C4—C5—C6 | 119.7 (3) | C9—C8—H8 | 119.7 |
C1—C6—C5 | 120.9 (2) | C7—C8—H8 | 119.7 |
C12—C7—C8 | 118.0 (2) | C10—C9—H9 | 119.9 |
C12—C7—Sn1 | 121.8 (2) | C8—C9—H9 | 119.9 |
C8—C7—Sn1 | 120.1 (2) | C11—C10—H10 | 120.1 |
C9—C8—C7 | 120.7 (2) | C9—C10—H10 | 120.1 |
C10—C9—C8 | 120.3 (2) | C10—C11—H11 | 119.9 |
C11—C10—C9 | 119.8 (2) | C12—C11—H11 | 119.9 |
C10—C11—C12 | 120.2 (2) | C11—C12—H12 | 119.5 |
C11—C12—C7 | 121.0 (2) | C7—C12—H12 | 119.5 |
C14—C13—C18 | 117.5 (2) | C15—C14—H14 | 119.5 |
C14—C13—Sn1 | 121.3 (2) | C13—C14—H14 | 119.5 |
C18—C13—Sn1 | 121.1 (2) | C16—C15—H15 | 119.9 |
C15—C14—C13 | 121.0 (3) | C14—C15—H15 | 119.9 |
C16—C15—C14 | 120.3 (3) | C17—C16—H16 | 119.9 |
C17—C16—C15 | 120.2 (3) | C15—C16—H16 | 119.9 |
C16—C17—C18 | 119.7 (3) | C16—C17—H17 | 120.2 |
C17—C18—C13 | 121.3 (3) | C18—C17—H17 | 120.2 |
O2—C19—O1 | 129.2 (2) | C17—C18—H18 | 119.4 |
O2—C19—C20 | 118.6 (2) | C13—C18—H18 | 119.4 |
O1—C19—C20 | 112.2 (2) | N1—C21—H21 | 118.5 |
F3—C20—F1 | 108.1 (2) | C22—C21—H21 | 118.5 |
F3—C20—F2 | 107.0 (2) | C23—C22—H22 | 120.8 |
F1—C20—F2 | 106.0 (2) | C21—C22—H22 | 120.8 |
F3—C20—C19 | 112.0 (2) | C24—C23—H23 | 120.4 |
F1—C20—C19 | 112.4 (2) | C22—C23—H23 | 120.4 |
F2—C20—C19 | 110.9 (2) | C23—C24—H24 | 120.1 |
N1—C21—C22 | 123.1 (3) | C25—C24—H24 | 120.1 |
C23—C22—C21 | 118.4 (3) | C28—C27—H27 | 120.9 |
C24—C23—C22 | 119.1 (3) | C26—C27—H27 | 120.9 |
C23—C24—C25 | 119.8 (3) | C27—C28—H28 | 120.2 |
N1—C25—C24 | 121.6 (2) | C29—C28—H28 | 120.2 |
N1—C25—C26 | 116.0 (2) | C28—C29—H29 | 120.3 |
C24—C25—C26 | 122.4 (2) | C30—C29—H29 | 120.3 |
N2—C26—C27 | 122.5 (2) | C33—C32—H32 | 120.1 |
N2—C26—C25 | 116.5 (2) | C31—C32—H32 | 120.1 |
C27—C26—C25 | 121.0 (2) | C34—C33—H33 | 120.5 |
C28—C27—C26 | 118.2 (2) | C32—C33—H33 | 120.5 |
C27—C28—C29 | 119.7 (2) | C33—C34—H34 | 120.7 |
C28—C29—C30 | 119.5 (3) | C35—C34—H34 | 120.7 |
N2—C30—C29 | 121.8 (2) | N3—C35—H35 | 118.2 |
N2—C30—C31 | 117.7 (2) | C34—C35—H35 | 118.2 |
C29—C30—C31 | 120.6 (2) | ||
C7—Sn1—O1—C19 | −61.9 (2) | C15—C16—C17—C18 | −0.6 (5) |
C13—Sn1—O1—C19 | −179.1 (2) | C16—C17—C18—C13 | −0.2 (4) |
C1—Sn1—O1—C19 | 57.1 (2) | C14—C13—C18—C17 | 0.7 (4) |
C7—Sn1—C1—C6 | −39.5 (2) | Sn1—C13—C18—C17 | −180.0 (2) |
C13—Sn1—C1—C6 | 132.7 (2) | Sn1—O1—C19—O2 | 6.4 (3) |
O1—Sn1—C1—C6 | −139.6 (2) | Sn1—O1—C19—C20 | −173.5 (1) |
O1w—Sn1—C1—C6 | 46.5 (2) | O2—C19—C20—F3 | 13.2 (3) |
C7—Sn1—C1—C2 | 137.5 (2) | O1—C19—C20—F3 | −167.0 (2) |
C13—Sn1—C1—C2 | −50.3 (2) | O2—C19—C20—F1 | 135.1 (2) |
O1—Sn1—C1—C2 | 37.4 (2) | O1—C19—C20—F1 | −45.0 (3) |
O1w—Sn1—C1—C2 | −136.5 (2) | O2—C19—C20—F2 | −106.4 (3) |
C6—C1—C2—C3 | −1.7 (4) | O1—C19—C20—F2 | 73.5 (3) |
Sn1—C1—C2—C3 | −178.7 (2) | C25—N1—C21—C22 | 0.6 (3) |
C1—C2—C3—C4 | 0.0 (4) | N1—C21—C22—C23 | 0.6 (4) |
C2—C3—C4—C5 | 2.0 (4) | C21—C22—C23—C24 | −1.5 (4) |
C3—C4—C5—C6 | −2.2 (4) | C22—C23—C24—C25 | 1.3 (4) |
C2—C1—C6—C5 | 1.5 (4) | C21—N1—C25—C24 | −0.8 (3) |
Sn1—C1—C6—C5 | 178.5 (2) | C21—N1—C25—C26 | 177.8 (2) |
C4—C5—C6—C1 | 0.5 (4) | C23—C24—C25—N1 | −0.1 (4) |
C13—Sn1—C7—C12 | 179.8 (2) | C23—C24—C25—C26 | −178.6 (2) |
C1—Sn1—C7—C12 | −7.5 (2) | C30—N2—C26—C27 | 1.6 (3) |
O1—Sn1—C7—C12 | 88.2 (2) | C30—N2—C26—C25 | −176.1 (2) |
O1w—Sn1—C7—C12 | −96.9 (2) | N1—C25—C26—N2 | 31.8 (3) |
C13—Sn1—C7—C8 | −4.5 (2) | C24—C25—C26—N2 | −149.6 (2) |
C1—Sn1—C7—C8 | 168.2 (2) | N1—C25—C26—C27 | −145.9 (2) |
O1—Sn1—C7—C8 | −96.1 (2) | C24—C25—C26—C27 | 32.7 (3) |
O1w—Sn1—C7—C8 | 78.8 (2) | N2—C26—C27—C28 | −1.2 (4) |
C12—C7—C8—C9 | 0.6 (3) | C25—C26—C27—C28 | 176.4 (2) |
Sn1—C7—C8—C9 | −175.2 (2) | C26—C27—C28—C29 | 0.3 (4) |
C7—C8—C9—C10 | 0.5 (4) | C27—C28—C29—C30 | 0.2 (4) |
C8—C9—C10—C11 | −1.3 (4) | C26—N2—C30—C29 | −1.0 (3) |
C9—C10—C11—C12 | 1.1 (4) | C26—N2—C30—C31 | 178.1 (2) |
C10—C11—C12—C7 | 0.0 (4) | C28—C29—C30—N2 | 0.1 (4) |
C8—C7—C12—C11 | −0.9 (3) | C28—C29—C30—C31 | −178.9 (2) |
Sn1—C7—C12—C11 | 174.9 (2) | C35—N3—C31—C32 | 0.4 (4) |
C7—Sn1—C13—C14 | −133.3 (2) | C35—N3—C31—C30 | −178.9 (2) |
C1—Sn1—C13—C14 | 54.5 (3) | N2—C30—C31—N3 | −25.5 (3) |
O1—Sn1—C13—C14 | −35.1 (2) | C29—C30—C31—N3 | 153.6 (2) |
O1w—Sn1—C13—C14 | 143.5 (2) | N2—C30—C31—C32 | 155.2 (2) |
C7—Sn1—C13—C18 | 47.4 (2) | C29—C30—C31—C32 | −25.7 (4) |
C1—Sn1—C13—C18 | −124.8 (2) | N3—C31—C32—C33 | 0.2 (4) |
O1—Sn1—C13—C18 | 145.6 (2) | C30—C31—C32—C33 | 179.4 (2) |
O1w—Sn1—C13—C18 | −35.7 (2) | C31—C32—C33—C34 | −0.4 (4) |
C18—C13—C14—C15 | −0.4 (5) | C32—C33—C34—C35 | 0.2 (4) |
Sn1—C13—C14—C15 | −179.8 (3) | C31—N3—C35—C34 | −0.7 (4) |
C13—C14—C15—C16 | −0.3 (6) | C33—C34—C35—N3 | 0.4 (4) |
C14—C15—C16—C17 | 0.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···N1 | 0.84 (1) | 1.93 (1) | 2.771 (3) | 171 (3) |
O1w—H1w2···N3 | 0.84 (1) | 1.96 (1) | 2.797 (3) | 173 (3) |
Experimental details
Crystal data | |
Chemical formula | [Sn(C2F3O2)(C6H5)3(H2O)]·C15H11N3 |
Mr | 714.29 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 158 |
a, b, c (Å) | 10.4257 (7), 10.0510 (7), 30.025 (2) |
β (°) | 94.265 (1) |
V (Å3) | 3137.6 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.87 |
Crystal size (mm) | 0.50 × 0.24 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.744, 0.877 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 39984, 6320, 5021 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.062, 0.95 |
No. of reflections | 6320 |
No. of parameters | 414 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.50, −0.43 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
Sn1—C1 | 2.130 (2) | Sn1—O1 | 2.221 (2) |
Sn1—C7 | 2.126 (2) | Sn1—O1w | 2.274 (2) |
Sn1—C13 | 2.126 (2) | ||
C1—Sn1—C7 | 118.5 (1) | C7—Sn1—O1 | 98.4 (1) |
C1—Sn1—C13 | 123.8 (1) | C7—Sn1—O1w | 85.8 (1) |
C1—Sn1—O1 | 91.0 (1) | C13—Sn1—O1 | 87.5 (1) |
C1—Sn1—O1w | 91.4 (1) | C13—Sn1—O1w | 86.0 (1) |
C7—Sn1—C13 | 117.3 (1) | O1—Sn1—O1w | 173.4 (1) |
In our previously reported structure of the 1:1 complex of aquatrifluoroacetatotriphenyltin and 2,4,6-tris(2-pyridyl)-1,3,5-triazine (Chee et al., 2002), the water molecule [Sn← O = 2.311 (3) Å] forms hydrogen bonds to two of the N atoms of the 1-pyridyl and 3-pyridyl rings of the N-heterocycle [O···N = 2.841 (4) and 2.826 (4) Å]; the N atom in the 2-position of the triazine ring is not involved in the interaction. The heterocyclic ligand is relatively flat, the 1-pyridyl and 3-pyridyl rings being twisted by only 7.7 (2) and 13.4 (2)° with respect to the triazine ring. Without the 5-pyridyl group, the resulting N-heterocycle, viz. terpyridine, also furnishes a similar outer-sphere coordination complex. However, the terpyridine ligand in the title complex, (I) (Fig. 1), is severely twisted, the dihedral angle of the two outer rings with respect to the central pyridyl ring being 25.6 (1) and 32.7 (1)°. The twist contrasts with the virtually flat conformation of terpyridine itself, the corresponding dihedral angles being only only 5.1 and 7.2°. As the ligand exists in the trans,trans-conformation in the solid state (and also in solution) (Bessel et al., 1992), it would have to reorganize itself in order to function as a terdentate chelate. Interestingly, the two terpyridine ligands in 2-methyl-3-trimethylsilyl-2,3-dicarba-1-stanna-closo-heptaborane(6) bis(terpyridine), both exist in the cis,cis-conformation, although only one of them chelates coordinated to the SnII atom (Siriwardane & Hosmane, 1988).
The ligand also forms outer-sphere coordination complexes with triphenyltin chloride [Sn—Owater = 2.317 (2) Å; Prasad et al., 1982] and triphenyltin isothiocyanate [Sn—Owater = 2.252 (2) Å; Prasad & Smith, 1982]; the ligand is also severely twisted [14.3 (3) and 32.0 (2)° in the chloride, and 19.6 (3) and 29.5 (3)° in the isothiocyanate]. The Sn—Owater bond in the trifluoroacetate is similar to the distances found in the two complexes, but is much shorter than that [Sn—Owater = 2.335 (4) Å] in the 1,10-phenanthroline adduct, which has a different hydrogen-bonding feature (Ng et al., 1996).