Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052695/bg2120sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052695/bg2120Isup2.hkl |
CCDC reference: 667228
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.041
- wR factor = 0.085
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level G 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 ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 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 0 ALERT type 5 Informative message, check
In recent years, there have been many reports of the synthesis and structure determination of various organotin(IV) compounds (Lockhart et al., 1987; Teoh et al., 1997; Basu et al., 2005). Among these, several structures of Ph3SnCl(H2O) cocrystallized with other molecules have been determined, for example 3-[2-(1,10-phenanthrolyl)]-5,6-diphenyl-1,2,4-triazine (Ladd et al., 1984), 3,4,7,8-tetramethyl-1,10-phenanthroline (Ng & Kumar Das, 1996) and [N,N'-bis(3-methoxysalicylidene)propane-1,3-diamine]nickel(II) (Clarke et al., 1994).
A mixture of Ph3SnCl (0.385 g, 1 mmol) and 2-(1-(4-pyridylmethyl)-1H-imidazol-2-yl)pyridine (0.236 g, 1 mmol) in ethanol (13 ml) was stirred for 0.5 h. The mixture was then transferred and sealed into an 18 ml Teflon-lined autoclave, which was heated at 150 °C for 89 h. After the mixture was cooled to room temperature, colorless blocks of the title complex were filtered off, washed with diethylether and dried at ambient temperature in air (yield 49% based on Sn).
All H atoms on C atoms were poisitioned geometrically and refined as riding atoms, with C—H = 0.93–0.97 Å, and Uiso = 1.2Ueq (C). The H atoms of the coordinated water molecule were located in a difference Fourier map and then refined isotropically.
In recent years, there have been many reports on the syntheses and structure determinations of various organotin(IV) compounds (Lockhart et al., 1987; Teoh et al., 1997; Basu et al., 2005). Among them, several structures of Ph3SnCl(H2O) cocrystallized with other molecules have been determined, for example 3-[2-(1,10-phenanthrolyl)]-5,6-diphenyl-1,2,4-triazine (Ladd et al., 1984), 3,4,7,8-tetramethyl-1,10-phenanthroline (Ng & Kumar Das, 1996), [N,N'-bis(3-methoxysalicylidene)propane-1,3-diamine]nickel(II) (Clarke et al., 1994), etc. In all these structures, the coordinated water molecule in Ph3SnCl(H2O) is hydrogen bonded to the cocrystallized molecules in the structure.
In the molecular structure of the title compound, {[(C6H5)3SnCl(H2O)](C14H12N4)} (I), the Sn atom is five-coordinated in a slightly distorted trigonal–bipyramidal geometry by three C atoms of three phenyl groups, one Cl- anion and one water molecule in the axial positions (Fig. 1). The slight distortion from the ideal trigonal–bipyramidal geometry is reflected in the O1—Sn1—Cl1 angle of 177.59 (7)°, and the three C—Sn—C angles of 116.65 (13) °, 117.37 (13) ° and 124.52 (13) °. The coordinated water molecule in Ph3SnCl(H2O) links the cocrystallized molecules to generate an infinite chain structure through O—H···N hydrogen bonds (Fig. 2 and Table 2).
In recent years, there have been many reports of the synthesis and structure determination of various organotin(IV) compounds (Lockhart et al., 1987; Teoh et al., 1997; Basu et al., 2005). Among these, several structures of Ph3SnCl(H2O) cocrystallized with other molecules have been determined, for example 3-[2-(1,10-phenanthrolyl)]-5,6-diphenyl-1,2,4-triazine (Ladd et al., 1984), 3,4,7,8-tetramethyl-1,10-phenanthroline (Ng & Kumar Das, 1996) and [N,N'-bis(3-methoxysalicylidene)propane-1,3-diamine]nickel(II) (Clarke et al., 1994).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. Ball-stick representation of the infinite chain of (I). |
[Sn(C6H5)3Cl(H2O)]·C14H12N4 | Z = 2 |
Mr = 639.73 | F(000) = 648 |
Triclinic, P1 | Dx = 1.452 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 10.643 (2) Å | Cell parameters from 9072 reflections |
b = 11.165 (2) Å | θ = 1.6–28.3° |
c = 13.196 (3) Å | µ = 1.00 mm−1 |
α = 89.945 (4)° | T = 293 K |
β = 71.953 (3)° | Block, colourless |
γ = 79.463 (3)° | 0.35 × 0.32 × 0.28 mm |
V = 1463.2 (5) Å3 |
Bruker APEX CCD area-detector diffractometer | 6576 independent reflections |
Radiation source: fine-focus sealed tube | 4836 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 28.3°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→14 |
Tmin = 0.71, Tmax = 0.76 | k = −12→14 |
9072 measured reflections | l = −16→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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0226P)2 + 0.8978P] where P = (Fo2 + 2Fc2)/3 |
6576 reflections | (Δ/σ)max < 0.001 |
360 parameters | Δρmax = 0.40 e Å−3 |
3 restraints | Δρmin = −0.42 e Å−3 |
[Sn(C6H5)3Cl(H2O)]·C14H12N4 | γ = 79.463 (3)° |
Mr = 639.73 | V = 1463.2 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.643 (2) Å | Mo Kα radiation |
b = 11.165 (2) Å | µ = 1.00 mm−1 |
c = 13.196 (3) Å | T = 293 K |
α = 89.945 (4)° | 0.35 × 0.32 × 0.28 mm |
β = 71.953 (3)° |
Bruker APEX CCD area-detector diffractometer | 6576 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4836 reflections with I > 2σ(I) |
Tmin = 0.71, Tmax = 0.76 | Rint = 0.019 |
9072 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 3 restraints |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.40 e Å−3 |
6576 reflections | Δρmin = −0.42 e Å−3 |
360 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 | 0.14373 (2) | 0.73666 (2) | 0.74054 (2) | 0.05096 (9) | |
C1 | 0.3501 (4) | 0.5030 (4) | 0.6384 (3) | 0.0708 (12) | |
H1 | 0.4123 | 0.5516 | 0.6388 | 0.085* | |
C2 | 0.3954 (5) | 0.3825 (4) | 0.5992 (4) | 0.0902 (15) | |
H2 | 0.4873 | 0.3507 | 0.5745 | 0.108* | |
C3 | 0.3061 (6) | 0.3105 (4) | 0.5965 (4) | 0.0867 (14) | |
H3 | 0.3370 | 0.2293 | 0.5710 | 0.104* | |
C4 | 0.1720 (5) | 0.3569 (4) | 0.6312 (4) | 0.0771 (12) | |
H4 | 0.1111 | 0.3084 | 0.6272 | 0.093* | |
C5 | 0.1252 (4) | 0.4773 (4) | 0.6728 (3) | 0.0635 (10) | |
H5 | 0.0330 | 0.5076 | 0.6982 | 0.076* | |
C6 | 0.2135 (3) | 0.5526 (3) | 0.6771 (3) | 0.0487 (8) | |
C7 | 0.1129 (4) | 0.8498 (4) | 0.9625 (3) | 0.0711 (11) | |
H7 | 0.1685 | 0.9000 | 0.9230 | 0.085* | |
C8 | 0.0711 (5) | 0.8622 (5) | 1.0732 (4) | 0.0886 (14) | |
H8 | 0.0973 | 0.9216 | 1.1073 | 0.106* | |
C9 | −0.0080 (5) | 0.7878 (5) | 1.1320 (4) | 0.0894 (15) | |
H9 | −0.0346 | 0.7952 | 1.2062 | 0.107* | |
C10 | −0.0483 (4) | 0.7022 (5) | 1.0817 (4) | 0.0883 (15) | |
H10 | −0.1022 | 0.6512 | 1.1218 | 0.106* | |
C11 | −0.0093 (4) | 0.6913 (4) | 0.9717 (3) | 0.0715 (12) | |
H11 | −0.0390 | 0.6339 | 0.9383 | 0.086* | |
C12 | 0.0733 (3) | 0.7643 (3) | 0.9103 (3) | 0.0533 (9) | |
C13 | 0.1896 (3) | 0.8775 (3) | 0.6325 (3) | 0.0495 (8) | |
C14 | 0.3197 (4) | 0.8708 (3) | 0.5644 (3) | 0.0615 (10) | |
H14 | 0.3886 | 0.8104 | 0.5718 | 0.074* | |
C15 | 0.3484 (4) | 0.9522 (4) | 0.4860 (3) | 0.0713 (11) | |
H15 | 0.4359 | 0.9452 | 0.4401 | 0.086* | |
C16 | 0.2496 (5) | 1.0429 (4) | 0.4750 (4) | 0.0735 (12) | |
H16 | 0.2694 | 1.0978 | 0.4220 | 0.088* | |
C17 | 0.1220 (5) | 1.0523 (4) | 0.5422 (4) | 0.0733 (12) | |
H17 | 0.0545 | 1.1146 | 0.5354 | 0.088* | |
C18 | 0.0909 (4) | 0.9704 (3) | 0.6207 (3) | 0.0607 (10) | |
H18 | 0.0029 | 0.9780 | 0.6659 | 0.073* | |
C19 | 0.3493 (4) | 0.4092 (4) | 1.0023 (3) | 0.0626 (10) | |
H19 | 0.3018 | 0.3738 | 1.0623 | 0.075* | |
C20 | 0.3158 (4) | 0.5232 (4) | 0.9716 (3) | 0.0625 (10) | |
H20 | 0.2388 | 0.5796 | 1.0077 | 0.075* | |
C21 | 0.5020 (3) | 0.4413 (3) | 0.8543 (3) | 0.0502 (8) | |
C22 | 0.6210 (4) | 0.4207 (3) | 0.7590 (3) | 0.0525 (9) | |
C23 | 0.6732 (4) | 0.5173 (4) | 0.7092 (3) | 0.0710 (11) | |
H23 | 0.6352 | 0.5971 | 0.7363 | 0.085* | |
C24 | 0.7829 (5) | 0.4929 (5) | 0.6184 (4) | 0.0846 (14) | |
H24 | 0.8215 | 0.5562 | 0.5840 | 0.102* | |
C25 | 0.8350 (5) | 0.3743 (6) | 0.5789 (4) | 0.0874 (14) | |
H25 | 0.9081 | 0.3559 | 0.5169 | 0.105* | |
C26 | 0.7766 (5) | 0.2846 (5) | 0.6333 (4) | 0.0854 (14) | |
H26 | 0.8119 | 0.2043 | 0.6065 | 0.102* | |
C27 | 0.5463 (4) | 0.2360 (3) | 0.9335 (3) | 0.0664 (11) | |
H27A | 0.5299 | 0.2193 | 1.0081 | 0.080* | |
H27B | 0.6414 | 0.2375 | 0.9026 | 0.080* | |
C28 | 0.4026 (4) | 0.1447 (4) | 0.8450 (4) | 0.0734 (12) | |
H28 | 0.3443 | 0.2197 | 0.8535 | 0.088* | |
C29 | 0.5133 (4) | 0.1337 (3) | 0.8775 (3) | 0.0541 (9) | |
C30 | 0.5958 (4) | 0.0205 (3) | 0.8614 (3) | 0.0652 (11) | |
H30 | 0.6738 | 0.0088 | 0.8808 | 0.078* | |
C31 | 0.5626 (4) | −0.0744 (4) | 0.8167 (3) | 0.0651 (11) | |
H31 | 0.6196 | −0.1502 | 0.8070 | 0.078* | |
N1 | 0.4532 (3) | −0.0648 (3) | 0.7861 (3) | 0.0664 (9) | |
Cl1 | −0.09058 (10) | 0.75149 (10) | 0.73063 (10) | 0.0815 (3) | |
C32 | 0.3762 (4) | 0.0448 (4) | 0.7993 (4) | 0.0767 (12) | |
H32 | 0.3006 | 0.0553 | 0.7766 | 0.092* | |
N2 | 0.4681 (3) | 0.3567 (3) | 0.9264 (2) | 0.0548 (7) | |
N3 | 0.4103 (3) | 0.5435 (3) | 0.8808 (3) | 0.0563 (8) | |
N4 | 0.6719 (3) | 0.3049 (3) | 0.7225 (3) | 0.0718 (9) | |
O1 | 0.3576 (2) | 0.7300 (2) | 0.7549 (2) | 0.0511 (6) | |
H1A | 0.389 (4) | 0.7939 (19) | 0.760 (3) | 0.083 (15)* | |
H1B | 0.373 (3) | 0.683 (2) | 0.802 (2) | 0.066 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.04668 (14) | 0.04605 (15) | 0.05895 (16) | −0.00622 (10) | −0.01647 (11) | 0.00314 (11) |
C1 | 0.068 (3) | 0.064 (3) | 0.085 (3) | −0.001 (2) | −0.037 (2) | −0.023 (2) |
C2 | 0.080 (3) | 0.075 (3) | 0.115 (4) | 0.016 (3) | −0.048 (3) | −0.039 (3) |
C3 | 0.117 (4) | 0.056 (3) | 0.099 (4) | −0.001 (3) | −0.059 (3) | −0.014 (2) |
C4 | 0.104 (4) | 0.054 (3) | 0.085 (3) | −0.033 (3) | −0.038 (3) | 0.006 (2) |
C5 | 0.073 (3) | 0.057 (2) | 0.064 (3) | −0.021 (2) | −0.020 (2) | 0.007 (2) |
C6 | 0.056 (2) | 0.047 (2) | 0.046 (2) | −0.0089 (17) | −0.0212 (17) | 0.0006 (16) |
C7 | 0.066 (3) | 0.064 (3) | 0.070 (3) | −0.010 (2) | −0.004 (2) | −0.009 (2) |
C8 | 0.082 (3) | 0.084 (3) | 0.088 (4) | −0.008 (3) | −0.014 (3) | −0.024 (3) |
C9 | 0.091 (4) | 0.113 (4) | 0.051 (3) | −0.004 (3) | −0.012 (3) | −0.005 (3) |
C10 | 0.066 (3) | 0.099 (4) | 0.080 (3) | −0.015 (3) | 0.006 (3) | 0.018 (3) |
C11 | 0.055 (2) | 0.072 (3) | 0.076 (3) | −0.013 (2) | −0.003 (2) | 0.002 (2) |
C12 | 0.0454 (19) | 0.053 (2) | 0.055 (2) | −0.0035 (17) | −0.0094 (17) | 0.0019 (18) |
C13 | 0.055 (2) | 0.0420 (19) | 0.055 (2) | −0.0073 (16) | −0.0221 (18) | −0.0020 (16) |
C14 | 0.061 (2) | 0.058 (2) | 0.063 (2) | −0.0031 (19) | −0.021 (2) | 0.009 (2) |
C15 | 0.074 (3) | 0.071 (3) | 0.065 (3) | −0.018 (2) | −0.014 (2) | 0.010 (2) |
C16 | 0.101 (3) | 0.057 (3) | 0.074 (3) | −0.026 (3) | −0.037 (3) | 0.016 (2) |
C17 | 0.090 (3) | 0.049 (2) | 0.088 (3) | −0.004 (2) | −0.043 (3) | 0.010 (2) |
C18 | 0.061 (2) | 0.051 (2) | 0.069 (3) | −0.0010 (18) | −0.025 (2) | 0.0017 (19) |
C19 | 0.073 (3) | 0.066 (3) | 0.055 (2) | −0.022 (2) | −0.024 (2) | 0.010 (2) |
C20 | 0.063 (2) | 0.060 (3) | 0.065 (3) | −0.008 (2) | −0.021 (2) | −0.004 (2) |
C21 | 0.056 (2) | 0.042 (2) | 0.062 (2) | −0.0138 (17) | −0.0285 (18) | 0.0028 (17) |
C22 | 0.056 (2) | 0.056 (2) | 0.055 (2) | −0.0131 (18) | −0.0300 (18) | 0.0059 (18) |
C23 | 0.074 (3) | 0.062 (3) | 0.081 (3) | −0.018 (2) | −0.027 (2) | 0.016 (2) |
C24 | 0.075 (3) | 0.109 (4) | 0.077 (3) | −0.030 (3) | −0.026 (3) | 0.030 (3) |
C25 | 0.063 (3) | 0.120 (5) | 0.073 (3) | −0.009 (3) | −0.018 (2) | −0.009 (3) |
C26 | 0.073 (3) | 0.087 (4) | 0.091 (4) | −0.006 (3) | −0.023 (3) | −0.023 (3) |
C27 | 0.086 (3) | 0.048 (2) | 0.080 (3) | −0.016 (2) | −0.046 (2) | 0.016 (2) |
C28 | 0.070 (3) | 0.042 (2) | 0.119 (4) | −0.008 (2) | −0.047 (3) | 0.004 (2) |
C29 | 0.061 (2) | 0.044 (2) | 0.063 (2) | −0.0142 (18) | −0.0252 (19) | 0.0146 (18) |
C30 | 0.059 (2) | 0.050 (2) | 0.093 (3) | −0.0114 (19) | −0.032 (2) | 0.012 (2) |
C31 | 0.066 (3) | 0.047 (2) | 0.078 (3) | −0.006 (2) | −0.019 (2) | 0.012 (2) |
N1 | 0.065 (2) | 0.0461 (19) | 0.090 (3) | −0.0166 (16) | −0.0234 (19) | 0.0061 (17) |
Cl1 | 0.0500 (5) | 0.0848 (8) | 0.1148 (9) | −0.0104 (5) | −0.0346 (6) | 0.0109 (7) |
C32 | 0.070 (3) | 0.056 (3) | 0.113 (4) | −0.015 (2) | −0.040 (3) | 0.003 (2) |
N2 | 0.0636 (19) | 0.0428 (17) | 0.065 (2) | −0.0126 (15) | −0.0286 (17) | 0.0046 (15) |
N3 | 0.0599 (18) | 0.0446 (18) | 0.068 (2) | −0.0069 (15) | −0.0272 (17) | 0.0020 (15) |
N4 | 0.061 (2) | 0.062 (2) | 0.086 (3) | −0.0059 (17) | −0.0170 (19) | −0.0113 (19) |
O1 | 0.0558 (14) | 0.0410 (14) | 0.0620 (17) | −0.0114 (13) | −0.0255 (13) | 0.0081 (13) |
Sn1—C6 | 2.129 (3) | C17—H17 | 0.9300 |
Sn1—C12 | 2.134 (4) | C18—H18 | 0.9300 |
Sn1—C13 | 2.142 (3) | C19—C20 | 1.354 (5) |
Sn1—O1 | 2.329 (2) | C19—N2 | 1.375 (5) |
Sn1—Cl1 | 2.5128 (11) | C19—H19 | 0.9300 |
C1—C2 | 1.387 (5) | C20—N3 | 1.353 (5) |
C1—C6 | 1.388 (5) | C20—H20 | 0.9300 |
C1—H1 | 0.9300 | C21—N3 | 1.326 (4) |
C2—C3 | 1.360 (6) | C21—N2 | 1.356 (4) |
C2—H2 | 0.9300 | C21—C22 | 1.464 (5) |
C3—C4 | 1.357 (6) | C22—N4 | 1.335 (4) |
C3—H3 | 0.9300 | C22—C23 | 1.376 (5) |
C4—C5 | 1.395 (5) | C23—C24 | 1.375 (6) |
C4—H4 | 0.9300 | C23—H23 | 0.9300 |
C5—C6 | 1.384 (5) | C24—C25 | 1.373 (6) |
C5—H5 | 0.9300 | C24—H24 | 0.9300 |
C7—C12 | 1.375 (5) | C25—C26 | 1.362 (6) |
C7—C8 | 1.388 (6) | C25—H25 | 0.9300 |
C7—H7 | 0.9300 | C26—N4 | 1.332 (5) |
C8—C9 | 1.361 (6) | C26—H26 | 0.9300 |
C8—H8 | 0.9300 | C27—N2 | 1.468 (4) |
C9—C10 | 1.365 (6) | C27—C29 | 1.511 (5) |
C9—H9 | 0.9300 | C27—H27A | 0.9700 |
C10—C11 | 1.380 (6) | C27—H27B | 0.9700 |
C10—H10 | 0.9300 | C28—C29 | 1.359 (5) |
C11—C12 | 1.384 (5) | C28—C32 | 1.380 (5) |
C11—H11 | 0.9300 | C28—H28 | 0.9300 |
C13—C18 | 1.380 (5) | C29—C30 | 1.376 (5) |
C13—C14 | 1.387 (5) | C30—C31 | 1.365 (5) |
C14—C15 | 1.376 (5) | C30—H30 | 0.9300 |
C14—H14 | 0.9300 | C31—N1 | 1.332 (5) |
C15—C16 | 1.362 (5) | C31—H31 | 0.9300 |
C15—H15 | 0.9300 | N1—C32 | 1.321 (5) |
C16—C17 | 1.358 (6) | C32—H32 | 0.9300 |
C16—H16 | 0.9300 | O1—H1A | 0.85 (3) |
C17—C18 | 1.384 (5) | O1—H1B | 0.85 (3) |
C6—Sn1—C12 | 116.65 (13) | C16—C17—H17 | 119.5 |
C6—Sn1—C13 | 117.37 (13) | C18—C17—H17 | 119.5 |
C12—Sn1—C13 | 124.52 (13) | C13—C18—C17 | 120.5 (4) |
C6—Sn1—O1 | 86.85 (11) | C13—C18—H18 | 119.8 |
C12—Sn1—O1 | 85.73 (11) | C17—C18—H18 | 119.8 |
C13—Sn1—O1 | 85.47 (11) | C20—C19—N2 | 105.8 (3) |
C6—Sn1—Cl1 | 95.43 (10) | C20—C19—H19 | 127.1 |
C12—Sn1—Cl1 | 92.53 (10) | N2—C19—H19 | 127.1 |
C13—Sn1—Cl1 | 94.16 (10) | N3—C20—C19 | 110.4 (4) |
O1—Sn1—Cl1 | 177.59 (7) | N3—C20—H20 | 124.8 |
C2—C1—C6 | 121.2 (4) | C19—C20—H20 | 124.8 |
C2—C1—H1 | 119.4 | N3—C21—N2 | 110.3 (3) |
C6—C1—H1 | 119.4 | N3—C21—C22 | 125.2 (3) |
C3—C2—C1 | 120.4 (4) | N2—C21—C22 | 124.5 (3) |
C3—C2—H2 | 119.8 | N4—C22—C23 | 122.7 (4) |
C1—C2—H2 | 119.8 | N4—C22—C21 | 116.4 (3) |
C4—C3—C2 | 120.0 (4) | C23—C22—C21 | 120.8 (4) |
C4—C3—H3 | 120.0 | C24—C23—C22 | 118.4 (4) |
C2—C3—H3 | 120.0 | C24—C23—H23 | 120.8 |
C3—C4—C5 | 120.1 (4) | C22—C23—H23 | 120.8 |
C3—C4—H4 | 120.0 | C25—C24—C23 | 119.5 (5) |
C5—C4—H4 | 120.0 | C25—C24—H24 | 120.2 |
C6—C5—C4 | 121.2 (4) | C23—C24—H24 | 120.2 |
C6—C5—H5 | 119.4 | C26—C25—C24 | 118.1 (5) |
C4—C5—H5 | 119.4 | C26—C25—H25 | 121.0 |
C5—C6—C1 | 117.1 (3) | C24—C25—H25 | 121.0 |
C5—C6—Sn1 | 121.7 (3) | N4—C26—C25 | 123.9 (5) |
C1—C6—Sn1 | 121.2 (3) | N4—C26—H26 | 118.0 |
C12—C7—C8 | 121.0 (4) | C25—C26—H26 | 118.0 |
C12—C7—H7 | 119.5 | N2—C27—C29 | 113.6 (3) |
C8—C7—H7 | 119.5 | N2—C27—H27A | 108.8 |
C9—C8—C7 | 120.2 (5) | C29—C27—H27A | 108.8 |
C9—C8—H8 | 119.9 | N2—C27—H27B | 108.8 |
C7—C8—H8 | 119.9 | C29—C27—H27B | 108.8 |
C8—C9—C10 | 119.7 (4) | H27A—C27—H27B | 107.7 |
C8—C9—H9 | 120.1 | C29—C28—C32 | 120.2 (4) |
C10—C9—H9 | 120.1 | C29—C28—H28 | 119.9 |
C9—C10—C11 | 120.2 (4) | C32—C28—H28 | 119.9 |
C9—C10—H10 | 119.9 | C28—C29—C30 | 116.9 (4) |
C11—C10—H10 | 119.9 | C28—C29—C27 | 124.0 (3) |
C10—C11—C12 | 121.0 (4) | C30—C29—C27 | 119.1 (3) |
C10—C11—H11 | 119.5 | C31—C30—C29 | 119.7 (4) |
C12—C11—H11 | 119.5 | C31—C30—H30 | 120.2 |
C7—C12—C11 | 117.9 (4) | C29—C30—H30 | 120.2 |
C7—C12—Sn1 | 121.9 (3) | N1—C31—C30 | 123.8 (4) |
C11—C12—Sn1 | 120.2 (3) | N1—C31—H31 | 118.1 |
C18—C13—C14 | 117.7 (3) | C30—C31—H31 | 118.1 |
C18—C13—Sn1 | 122.0 (3) | C32—N1—C31 | 116.2 (3) |
C14—C13—Sn1 | 119.9 (3) | N1—C32—C28 | 123.2 (4) |
C15—C14—C13 | 120.9 (4) | N1—C32—H32 | 118.4 |
C15—C14—H14 | 119.5 | C28—C32—H32 | 118.4 |
C13—C14—H14 | 119.5 | C21—N2—C19 | 107.1 (3) |
C16—C15—C14 | 120.6 (4) | C21—N2—C27 | 128.5 (3) |
C16—C15—H15 | 119.7 | C19—N2—C27 | 124.0 (3) |
C14—C15—H15 | 119.7 | C21—N3—C20 | 106.3 (3) |
C17—C16—C15 | 119.3 (4) | C26—N4—C22 | 117.4 (4) |
C17—C16—H16 | 120.3 | Sn1—O1—H1A | 123 (2) |
C15—C16—H16 | 120.3 | Sn1—O1—H1B | 112 (2) |
C16—C17—C18 | 120.9 (4) | H1A—O1—H1B | 108.3 (16) |
C6—C1—C2—C3 | 0.9 (7) | Sn1—C13—C14—C15 | 172.4 (3) |
C1—C2—C3—C4 | 0.8 (8) | C13—C14—C15—C16 | 1.3 (6) |
C2—C3—C4—C5 | −2.1 (7) | C14—C15—C16—C17 | −0.1 (7) |
C3—C4—C5—C6 | 1.8 (6) | C15—C16—C17—C18 | −0.7 (7) |
C4—C5—C6—C1 | −0.1 (6) | C14—C13—C18—C17 | 0.9 (6) |
C4—C5—C6—Sn1 | −180.0 (3) | Sn1—C13—C18—C17 | −173.1 (3) |
C2—C1—C6—C5 | −1.2 (6) | C16—C17—C18—C13 | 0.2 (6) |
C2—C1—C6—Sn1 | 178.6 (3) | N2—C19—C20—N3 | −1.0 (4) |
C12—Sn1—C6—C5 | 78.9 (3) | N3—C21—C22—N4 | −154.8 (3) |
C13—Sn1—C6—C5 | −114.3 (3) | N2—C21—C22—N4 | 23.2 (5) |
O1—Sn1—C6—C5 | 162.5 (3) | N3—C21—C22—C23 | 23.2 (5) |
Cl1—Sn1—C6—C5 | −16.7 (3) | N2—C21—C22—C23 | −158.8 (3) |
C12—Sn1—C6—C1 | −101.0 (3) | N4—C22—C23—C24 | −0.4 (6) |
C13—Sn1—C6—C1 | 65.8 (3) | C21—C22—C23—C24 | −178.3 (4) |
O1—Sn1—C6—C1 | −17.4 (3) | C22—C23—C24—C25 | 1.4 (6) |
Cl1—Sn1—C6—C1 | 163.4 (3) | C23—C24—C25—C26 | −1.2 (7) |
C12—C7—C8—C9 | 1.3 (7) | C24—C25—C26—N4 | 0.0 (7) |
C7—C8—C9—C10 | −1.2 (8) | C32—C28—C29—C30 | 0.7 (6) |
C8—C9—C10—C11 | −0.2 (8) | C32—C28—C29—C27 | −176.6 (4) |
C9—C10—C11—C12 | 1.5 (7) | N2—C27—C29—C28 | −14.5 (6) |
C8—C7—C12—C11 | 0.0 (6) | N2—C27—C29—C30 | 168.2 (3) |
C8—C7—C12—Sn1 | −176.8 (3) | C28—C29—C30—C31 | −1.4 (6) |
C10—C11—C12—C7 | −1.3 (6) | C27—C29—C30—C31 | 176.1 (4) |
C10—C11—C12—Sn1 | 175.5 (3) | C29—C30—C31—N1 | 0.4 (6) |
C6—Sn1—C12—C7 | 132.9 (3) | C30—C31—N1—C32 | 1.3 (6) |
C13—Sn1—C12—C7 | −32.9 (4) | C31—N1—C32—C28 | −2.1 (6) |
O1—Sn1—C12—C7 | 48.6 (3) | C29—C28—C32—N1 | 1.1 (7) |
Cl1—Sn1—C12—C7 | −129.8 (3) | N3—C21—N2—C19 | −0.4 (4) |
C6—Sn1—C12—C11 | −43.8 (3) | C22—C21—N2—C19 | −178.6 (3) |
C13—Sn1—C12—C11 | 150.3 (3) | N3—C21—N2—C27 | −173.8 (3) |
O1—Sn1—C12—C11 | −128.1 (3) | C22—C21—N2—C27 | 7.9 (5) |
Cl1—Sn1—C12—C11 | 53.5 (3) | C20—C19—N2—C21 | 0.8 (4) |
C6—Sn1—C13—C18 | 125.8 (3) | C20—C19—N2—C27 | 174.6 (3) |
C12—Sn1—C13—C18 | −68.5 (3) | C29—C27—N2—C21 | −94.1 (4) |
O1—Sn1—C13—C18 | −150.2 (3) | C29—C27—N2—C19 | 93.4 (4) |
Cl1—Sn1—C13—C18 | 27.4 (3) | N2—C21—N3—C20 | −0.2 (4) |
C6—Sn1—C13—C14 | −48.1 (3) | C22—C21—N3—C20 | 178.0 (3) |
C12—Sn1—C13—C14 | 117.6 (3) | C19—C20—N3—C21 | 0.7 (4) |
O1—Sn1—C13—C14 | 36.0 (3) | C25—C26—N4—C22 | 1.1 (7) |
Cl1—Sn1—C13—C14 | −146.4 (3) | C23—C22—N4—C26 | −0.8 (6) |
C18—C13—C14—C15 | −1.7 (6) | C21—C22—N4—C26 | 177.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···N3 | 0.85 (3) | 1.92 (1) | 2.749 (4) | 165 (3) |
O1—H1A···N1i | 0.85 (3) | 1.90 (3) | 2.751 (4) | 174 (3) |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Sn(C6H5)3Cl(H2O)]·C14H12N4 |
Mr | 639.73 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.643 (2), 11.165 (2), 13.196 (3) |
α, β, γ (°) | 89.945 (4), 71.953 (3), 79.463 (3) |
V (Å3) | 1463.2 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.00 |
Crystal size (mm) | 0.35 × 0.32 × 0.28 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.71, 0.76 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9072, 6576, 4836 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.085, 1.02 |
No. of reflections | 6576 |
No. of parameters | 360 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.42 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···N3 | 0.85 (3) | 1.923 (12) | 2.749 (4) | 165 (3) |
O1—H1A···N1i | 0.85 (3) | 1.90 (3) | 2.751 (4) | 174 (3) |
Symmetry code: (i) x, y+1, z. |
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In recent years, there have been many reports on the syntheses and structure determinations of various organotin(IV) compounds (Lockhart et al., 1987; Teoh et al., 1997; Basu et al., 2005). Among them, several structures of Ph3SnCl(H2O) cocrystallized with other molecules have been determined, for example 3-[2-(1,10-phenanthrolyl)]-5,6-diphenyl-1,2,4-triazine (Ladd et al., 1984), 3,4,7,8-tetramethyl-1,10-phenanthroline (Ng & Kumar Das, 1996), [N,N'-bis(3-methoxysalicylidene)propane-1,3-diamine]nickel(II) (Clarke et al., 1994), etc. In all these structures, the coordinated water molecule in Ph3SnCl(H2O) is hydrogen bonded to the cocrystallized molecules in the structure.
In the molecular structure of the title compound, {[(C6H5)3SnCl(H2O)](C14H12N4)} (I), the Sn atom is five-coordinated in a slightly distorted trigonal–bipyramidal geometry by three C atoms of three phenyl groups, one Cl- anion and one water molecule in the axial positions (Fig. 1). The slight distortion from the ideal trigonal–bipyramidal geometry is reflected in the O1—Sn1—Cl1 angle of 177.59 (7)°, and the three C—Sn—C angles of 116.65 (13) °, 117.37 (13) ° and 124.52 (13) °. The coordinated water molecule in Ph3SnCl(H2O) links the cocrystallized molecules to generate an infinite chain structure through O—H···N hydrogen bonds (Fig. 2 and Table 2).