metal-organic compounds
(2-Hydroxybenzoato-κO)triphenyl(triphenylphosphine oxide-κO)tin(IV)
aLaboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and bLaboratoire de Réactivité et Chimie des Solides (LRCS), Université de Picardie Jules Verne, CNRS UMR 7314, 33 rue Saint Leu, 80039 Amiens, France
*Correspondence e-mail: dlibasse@gmail.com
The title compound, [Sn{C6H4(OH)COO}(C6H5)3{OP(C6H5)3}], is comprised of discrete molecules with the SnIV atom in a trigonal–bipyramidal coordination environment. The carboxylate O atom of the salicylate anion and the O atom of the triphenylphosphine oxide moiety are in the axial positions and the three ipso C atoms occupy the equatorial positions. An intramolecular O—H⋯O hydrogen bond is present in the anion between the hydroxy group and the carbonyl atom O of the carboxylate group.
Keywords: crystal structure; SnC3O2 coordination; trigonal-bipyramidal environment; intramolecular hydrogen bonding.
CCDC reference: 1517672
Structure description
The applications of organotin compounds in various fields (Omae, 1989) might explain the effort to synthesize and structurally determine new representatives of this family of compounds. In this context, the of the derivative C6H4(OH)CO2SnPh3 has been determined by Vollano et al. (1984), followed by a redetermination by Rauf et al. (2008). The structure consists of discrete molecules, with a tetrahedral coordination of the SnIV atom by the carboxylate –CO2 moiety and three phenyl groups. Related structures, viz. [Sn(C6H5COC6H4COO)(C6H5)3{(C6H5)3OP}] and [Sn(OOCC6HF4)(C6H5)3{(C6H5)3OP}] were reported by Diop et al. (2006) and Ma et al. (2006), respectively. In these structures, the OPPh3 moiety coordinates in a monodentate manner through the O atom to an SnPh3 residue. The scarcity of data on OPPh3 moieties coordinating to an SnPh3 residue that is additionally linked to a carboxylate group has prompted us to study the interactions between C6H4(OH)CO2SnPh3 and OPPh3, which has yielded the mononuclear title compound.
The molecular structure consists of a salicylate anion and a OPPh3 molecule, each coordinating to the SnIV atom of the SnPh3 group in a monodentate mode. The SnIV atom has a distorted trigonal–bipyramidal coordination environment, with the three phenyl groups in the equatorial positions (Fig. 1). The Sn—O1 bond involving the anion [2.124 (2) Å] and the Sn—O4 bond involving the OPPh3 group [2.451 (2) Å] are markedly different. The O1—Sn—O4 angle [171.65 (9)°] deviates from linearity. The sum of the C(ipso)—Sn—C(ipso) angles amounts to 357.36°. Comparable C(ipso)—Sn—C(ipso) angular sums of 359.07 and 357.63° were observed for the related structures reported by Diop et al. (2006) and Ma et al. (2006), respectively. The corresponding O—Sn—O angles in these structures are 175.46 (11) and 178.03 (11)°. The P—O4 bond length [1.489 (2) Å] in (I) is very similar to that in the structure reported by Ma et al. (1.486 Å), but different to the one reported by Diop et al. [1.511 (3) Å]. In the free OPPh3 ligand, the P—O bond length is 1.460 (1) Å (Bandoli et al., 1970). An intramolecular hydrogen bond is present between the hydroxy group and the C=O group of the carboxylate moiety (Table 1). In addition, a weak intramolecular C—H⋯O interaction between one of the phenyl H atoms and the carbonyl O atom is observed. The packing of molecules in the crystal has no special features and is depicted in Fig. 2.
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A search of the Cambridge Structural Database (Version 5.37 plus two updates; Groom et al., 2016) for structures containing salicylate moieties revealed 2105 hits while the Sn(Ph3)(OPPh3) fragment is present in 12 structures.
Synthesis and crystallization
C6H4(OH)CO2SnPh3, (I), was obtained from the condensation of salicylic acid (0.5 g, 4 mmol) with triphenyltin(IV) hydroxide (1.328 g, 4 mmol) in ethanol (50 ml). The title compound was obtained by reacting an ethanolic solution of (I) (0.487 g, 1 mmol) with OPPh3 (0.278 g, 1 mmol). The mixture was stirred for several hours. Slow solvent evaporation yielded colourless single crystals suitable for X-ray analysis.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1517672
https://doi.org/10.1107/S241431461601840X/wm4029sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461601840X/wm4029Isup2.hkl
Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).[Sn(C6H5)3(C7H5O3)(C18H15OP)] | Dx = 1.382 Mg m−3 |
Mr = 765.37 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 162157 reflections |
a = 9.3620 (3) Å | θ = 2.3–30.6° |
b = 17.7187 (7) Å | µ = 0.78 mm−1 |
c = 22.1796 (9) Å | T = 293 K |
V = 3679.2 (2) Å3 | Platelet, colorless |
Z = 4 | 0.10 × 0.05 × 0.02 mm |
F(000) = 1560 |
Bruker D8 Venture diffractometer | 11302 independent reflections |
Radiation source: fine-focus sealed-tube | 8849 reflections with I > 2σ(I) |
Detector resolution: 8.33 pixels mm-1 | Rint = 0.067 |
combinatoin of /w– and /f–scans | θmax = 30.6°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −13→13 |
Tmin = 0.69, Tmax = 0.75 | k = 0→25 |
11302 measured reflections | l = 0→31 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.063 | w = 1/[σ2(Fo2) + (0.0281P)2 + 0.2485P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
11302 reflections | Δρmax = 0.59 e Å−3 |
443 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Absolute structure: Flack x determined using 3310 quotients [(I+) - (I-)]/[(I+) + (I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.026 (5) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.92470 (2) | 0.23909 (2) | 0.79019 (2) | 0.03537 (6) | |
P1 | 1.10239 (8) | 0.33513 (4) | 0.65040 (3) | 0.03534 (18) | |
O1 | 0.8198 (3) | 0.17642 (14) | 0.85879 (10) | 0.0509 (6) | |
O2 | 0.9484 (5) | 0.1873 (2) | 1.03685 (13) | 0.0999 (11) | |
H2 | 0.9810 | 0.2090 | 1.0072 | 0.150* | |
O4 | 1.0151 (2) | 0.30745 (12) | 0.70199 (9) | 0.0432 (5) | |
O5 | 0.9652 (3) | 0.22689 (17) | 0.92674 (11) | 0.0664 (7) | |
C1 | 0.7881 (4) | 0.1037 (2) | 0.7273 (2) | 0.0715 (12) | |
H1 | 0.8369 | 0.0772 | 0.7571 | 0.086* | |
C2 | 0.6626 (5) | 0.1038 (2) | 0.9478 (2) | 0.0709 (12) | |
H2A | 0.6300 | 0.1020 | 0.9082 | 0.085* | |
C3 | 1.3704 (4) | 0.1963 (2) | 0.84320 (18) | 0.0570 (10) | |
H3 | 1.4309 | 0.2108 | 0.8744 | 0.068* | |
C4 | 1.3334 (5) | 0.1325 (2) | 0.7513 (2) | 0.0666 (11) | |
H4 | 1.3682 | 0.1026 | 0.7202 | 0.080* | |
C5 | 1.2605 (4) | 0.2594 (3) | 0.5616 (2) | 0.0773 (12) | |
H5 | 1.3313 | 0.2955 | 0.5673 | 0.093* | |
C6 | 0.8541 (5) | 0.5160 (2) | 0.61409 (18) | 0.0655 (11) | |
H6 | 0.7915 | 0.5465 | 0.6357 | 0.079* | |
C7 | 1.3407 (5) | 0.3410 (3) | 0.7212 (2) | 0.0781 (14) | |
H7 | 1.2989 | 0.3002 | 0.7408 | 0.094* | |
C8 | 1.2282 (3) | 0.21838 (18) | 0.84431 (15) | 0.0470 (8) | |
H8 | 1.1934 | 0.2465 | 0.8765 | 0.056* | |
C9 | 1.4699 (5) | 0.3668 (3) | 0.7407 (2) | 0.0880 (16) | |
H9 | 1.5149 | 0.3429 | 0.7728 | 0.106* | |
C10 | 1.5328 (4) | 0.4259 (2) | 0.7145 (2) | 0.0807 (13) | |
H10 | 1.6193 | 0.4443 | 0.7290 | 0.097* | |
C11 | 0.7223 (4) | 0.2195 (3) | 0.68116 (17) | 0.0694 (12) | |
H11 | 0.7264 | 0.2719 | 0.6793 | 0.083* | |
C12 | 1.3371 (5) | 0.4329 (3) | 0.6466 (2) | 0.0926 (18) | |
H12 | 1.2927 | 0.4567 | 0.6143 | 0.111* | |
C13 | 0.9754 (5) | 0.4869 (2) | 0.52329 (17) | 0.0633 (11) | |
H13 | 0.9944 | 0.4975 | 0.4830 | 0.076* | |
C14 | 1.0123 (3) | 0.40946 (17) | 0.61023 (13) | 0.0379 (7) | |
C15 | 1.0377 (4) | 0.2061 (2) | 0.58802 (17) | 0.0569 (9) | |
H15 | 0.9556 | 0.2059 | 0.6116 | 0.068* | |
C16 | 1.0562 (5) | 0.1502 (2) | 0.54498 (19) | 0.0739 (12) | |
H16 | 0.9870 | 0.1132 | 0.5396 | 0.089* | |
C17 | 1.2782 (7) | 0.2043 (3) | 0.5187 (2) | 0.1018 (18) | |
H17 | 1.3601 | 0.2039 | 0.4950 | 0.122* | |
C19 | 1.1918 (4) | 0.15498 (19) | 0.75101 (15) | 0.0478 (8) | |
H19 | 1.1326 | 0.1406 | 0.7193 | 0.057* | |
C20 | 0.9343 (4) | 0.41208 (17) | 0.81022 (14) | 0.0462 (7) | |
H20 | 1.0159 | 0.4098 | 0.7864 | 0.055* | |
C21 | 0.8898 (5) | 0.4812 (2) | 0.83324 (17) | 0.0612 (11) | |
H21 | 0.9422 | 0.5246 | 0.8251 | 0.073* | |
C22 | 0.7383 (4) | 0.3524 (2) | 0.85800 (15) | 0.0486 (8) | |
H22 | 0.6865 | 0.3091 | 0.8671 | 0.058* | |
C23 | 0.6935 (4) | 0.4217 (2) | 0.88043 (17) | 0.0638 (11) | |
H23 | 0.6118 | 0.4247 | 0.9041 | 0.077* | |
C24 | 0.8303 (6) | 0.1478 (2) | 1.02070 (18) | 0.0712 (12) | |
C25 | 0.6367 (7) | 0.1028 (6) | 0.6416 (3) | 0.136 (4) | |
H25 | 0.5850 | 0.0761 | 0.6128 | 0.163* | |
C26 | 0.7584 (8) | 0.1079 (3) | 1.0650 (2) | 0.104 (2) | |
H26 | 0.7906 | 0.1092 | 1.1047 | 0.124* | |
C27 | 0.6406 (5) | 0.1796 (5) | 0.6392 (2) | 0.110 (2) | |
H27 | 0.5893 | 0.2053 | 0.6097 | 0.132* | |
C28 | 0.7072 (7) | 0.0648 (4) | 0.6854 (3) | 0.116 (2) | |
H28 | 0.7013 | 0.0125 | 0.6873 | 0.139* | |
C29 | 1.4689 (6) | 0.4584 (3) | 0.6666 (3) | 0.113 (2) | |
H29 | 1.5135 | 0.4982 | 0.6468 | 0.136* | |
C30 | 0.8634 (4) | 0.1858 (2) | 0.91366 (16) | 0.0493 (9) | |
C31 | 0.7700 (5) | 0.4853 (2) | 0.86754 (19) | 0.0686 (12) | |
H31 | 0.7397 | 0.5317 | 0.8824 | 0.082* | |
C32 | 0.6431 (9) | 0.0675 (3) | 1.0507 (3) | 0.119 (3) | |
H32 | 0.5969 | 0.0403 | 1.0808 | 0.143* | |
C35 | 0.7822 (4) | 0.14517 (19) | 0.96130 (15) | 0.0533 (9) | |
C36 | 0.5897 (7) | 0.0646 (3) | 0.9921 (3) | 0.109 (2) | |
H36 | 0.5077 | 0.0373 | 0.9831 | 0.131* | |
C37 | 0.9180 (4) | 0.45468 (19) | 0.64161 (15) | 0.0544 (8) | |
H37 | 0.8972 | 0.4438 | 0.6817 | 0.065* | |
C38 | 1.0404 (4) | 0.4262 (2) | 0.55051 (14) | 0.0494 (9) | |
H38 | 1.1036 | 0.3963 | 0.5287 | 0.059* | |
C39 | 0.8835 (5) | 0.5316 (2) | 0.55470 (19) | 0.0655 (11) | |
H39 | 0.8407 | 0.5728 | 0.5360 | 0.079* | |
C40 | 1.1376 (3) | 0.26135 (19) | 0.59650 (13) | 0.0419 (7) | |
C41 | 1.2718 (3) | 0.37294 (19) | 0.67417 (14) | 0.0432 (8) | |
C42 | 1.1766 (6) | 0.1501 (3) | 0.5107 (2) | 0.0888 (16) | |
H42 | 1.1896 | 0.1130 | 0.4816 | 0.107* | |
C43 | 0.7969 (3) | 0.1814 (2) | 0.72536 (14) | 0.0445 (8) | |
C44 | 1.4224 (4) | 0.1539 (2) | 0.79708 (19) | 0.0653 (10) | |
H44 | 1.5179 | 0.1395 | 0.7967 | 0.078* | |
C45 | 1.1377 (3) | 0.19839 (15) | 0.79707 (14) | 0.0380 (7) | |
C46 | 0.8592 (3) | 0.34689 (17) | 0.82223 (13) | 0.0370 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03818 (10) | 0.03418 (9) | 0.03376 (9) | 0.00002 (9) | 0.00066 (9) | −0.00042 (8) |
P1 | 0.0374 (4) | 0.0353 (4) | 0.0333 (4) | −0.0011 (3) | 0.0024 (3) | 0.0046 (3) |
O1 | 0.0659 (16) | 0.0497 (14) | 0.0371 (13) | −0.0038 (12) | 0.0077 (12) | 0.0078 (11) |
O2 | 0.145 (3) | 0.107 (3) | 0.0478 (17) | 0.009 (3) | −0.009 (2) | 0.0028 (17) |
O4 | 0.0484 (12) | 0.0442 (12) | 0.0371 (12) | −0.0013 (9) | 0.0060 (10) | 0.0081 (10) |
O5 | 0.0704 (17) | 0.0788 (19) | 0.0501 (14) | −0.0145 (16) | 0.0038 (12) | 0.0017 (14) |
C1 | 0.062 (2) | 0.061 (2) | 0.091 (3) | −0.011 (2) | 0.013 (2) | −0.029 (2) |
C2 | 0.086 (3) | 0.062 (3) | 0.065 (3) | −0.002 (2) | 0.023 (2) | 0.009 (2) |
C3 | 0.045 (2) | 0.063 (2) | 0.063 (2) | −0.0003 (17) | −0.0127 (18) | 0.006 (2) |
C4 | 0.066 (3) | 0.064 (3) | 0.070 (3) | 0.020 (2) | 0.009 (2) | −0.011 (2) |
C5 | 0.068 (2) | 0.067 (3) | 0.097 (3) | −0.003 (2) | 0.034 (2) | −0.018 (3) |
C6 | 0.073 (3) | 0.050 (2) | 0.073 (3) | 0.019 (2) | 0.000 (2) | −0.004 (2) |
C7 | 0.060 (2) | 0.080 (3) | 0.094 (4) | −0.023 (2) | −0.026 (2) | 0.043 (3) |
C8 | 0.0473 (19) | 0.0444 (19) | 0.0494 (18) | −0.0006 (15) | −0.0019 (15) | −0.0003 (15) |
C9 | 0.064 (3) | 0.099 (4) | 0.101 (4) | −0.021 (3) | −0.035 (3) | 0.033 (3) |
C10 | 0.054 (2) | 0.073 (3) | 0.116 (4) | −0.015 (2) | −0.030 (3) | −0.001 (3) |
C11 | 0.045 (2) | 0.109 (4) | 0.055 (2) | −0.010 (2) | −0.0049 (17) | 0.001 (2) |
C12 | 0.080 (3) | 0.079 (3) | 0.119 (4) | −0.036 (3) | −0.046 (3) | 0.047 (3) |
C13 | 0.080 (3) | 0.062 (2) | 0.047 (2) | 0.003 (2) | −0.0060 (19) | 0.0218 (19) |
C14 | 0.0409 (17) | 0.0352 (16) | 0.0376 (17) | −0.0023 (13) | −0.0018 (13) | 0.0033 (13) |
C15 | 0.057 (2) | 0.056 (2) | 0.058 (2) | −0.0040 (18) | 0.0066 (17) | −0.0107 (18) |
C16 | 0.088 (3) | 0.056 (2) | 0.077 (3) | −0.005 (2) | −0.003 (3) | −0.018 (2) |
C17 | 0.112 (4) | 0.091 (4) | 0.103 (4) | 0.009 (3) | 0.057 (3) | −0.026 (3) |
C19 | 0.051 (2) | 0.0448 (19) | 0.0473 (19) | 0.0029 (16) | 0.0005 (16) | −0.0046 (15) |
C20 | 0.054 (2) | 0.0420 (17) | 0.0421 (16) | 0.0007 (18) | −0.0024 (16) | 0.0023 (12) |
C21 | 0.080 (3) | 0.0413 (19) | 0.063 (2) | 0.0031 (19) | −0.012 (2) | 0.0004 (17) |
C22 | 0.046 (2) | 0.054 (2) | 0.0459 (19) | 0.0026 (16) | 0.0040 (16) | −0.0044 (16) |
C23 | 0.060 (2) | 0.077 (3) | 0.055 (2) | 0.021 (2) | 0.0067 (19) | −0.016 (2) |
C24 | 0.109 (4) | 0.060 (3) | 0.045 (2) | 0.021 (3) | 0.015 (2) | 0.002 (2) |
C25 | 0.076 (4) | 0.227 (10) | 0.105 (5) | −0.058 (5) | 0.010 (4) | −0.095 (6) |
C26 | 0.196 (7) | 0.072 (3) | 0.043 (2) | 0.021 (4) | 0.037 (3) | 0.014 (2) |
C27 | 0.061 (3) | 0.209 (8) | 0.060 (3) | −0.021 (4) | −0.010 (2) | −0.019 (4) |
C28 | 0.093 (4) | 0.111 (5) | 0.143 (6) | −0.037 (4) | 0.025 (4) | −0.084 (4) |
C29 | 0.085 (4) | 0.084 (4) | 0.170 (6) | −0.048 (3) | −0.047 (4) | 0.051 (4) |
C30 | 0.062 (2) | 0.044 (2) | 0.0421 (19) | 0.0105 (17) | 0.0093 (17) | 0.0049 (15) |
C31 | 0.087 (3) | 0.051 (2) | 0.068 (3) | 0.022 (2) | −0.013 (2) | −0.019 (2) |
C32 | 0.192 (7) | 0.081 (4) | 0.085 (4) | −0.008 (4) | 0.079 (5) | 0.015 (3) |
C35 | 0.075 (3) | 0.0419 (19) | 0.0428 (19) | 0.0124 (19) | 0.0186 (18) | 0.0094 (15) |
C36 | 0.133 (5) | 0.089 (4) | 0.105 (4) | −0.027 (4) | 0.053 (4) | 0.009 (3) |
C37 | 0.066 (2) | 0.054 (2) | 0.0434 (17) | 0.012 (2) | 0.0039 (19) | 0.0048 (15) |
C38 | 0.056 (2) | 0.053 (2) | 0.0393 (17) | 0.0060 (16) | 0.0022 (15) | 0.0072 (15) |
C39 | 0.081 (3) | 0.041 (2) | 0.074 (3) | 0.0030 (19) | −0.020 (2) | 0.0190 (19) |
C40 | 0.0465 (16) | 0.0382 (16) | 0.0410 (15) | 0.0045 (15) | 0.0043 (13) | 0.0035 (15) |
C41 | 0.0411 (18) | 0.0420 (18) | 0.0466 (18) | −0.0036 (15) | −0.0024 (15) | 0.0013 (15) |
C42 | 0.125 (5) | 0.062 (3) | 0.079 (3) | 0.019 (3) | 0.013 (3) | −0.025 (2) |
C43 | 0.0335 (16) | 0.060 (2) | 0.0397 (18) | −0.0100 (16) | 0.0085 (13) | −0.0109 (15) |
C44 | 0.0451 (19) | 0.068 (2) | 0.083 (3) | 0.011 (2) | 0.005 (2) | 0.008 (2) |
C45 | 0.0412 (16) | 0.0288 (14) | 0.0440 (17) | 0.0015 (12) | 0.0001 (15) | 0.0049 (14) |
C46 | 0.0428 (17) | 0.0383 (17) | 0.0298 (15) | 0.0074 (14) | −0.0031 (13) | −0.0006 (12) |
Sn1—C45 | 2.126 (3) | C12—H12 | 0.9300 |
Sn1—O1 | 2.124 (2) | C13—C39 | 1.362 (6) |
Sn1—C46 | 2.128 (3) | C13—C38 | 1.376 (5) |
Sn1—C43 | 2.132 (3) | C13—H13 | 0.9300 |
Sn1—O4 | 2.451 (2) | C14—C37 | 1.380 (5) |
P1—O4 | 1.489 (2) | C14—C38 | 1.383 (4) |
P1—C14 | 1.800 (3) | C15—C40 | 1.368 (5) |
P1—C41 | 1.800 (3) | C15—C16 | 1.386 (5) |
P1—C40 | 1.802 (3) | C15—H15 | 0.9300 |
O1—C30 | 1.294 (4) | C16—C42 | 1.360 (6) |
O2—C24 | 1.357 (6) | C16—H16 | 0.9300 |
O2—H2 | 0.8200 | C17—C42 | 1.363 (7) |
O5—C30 | 1.234 (4) | C17—H17 | 0.9300 |
C1—C28 | 1.382 (7) | C19—C45 | 1.375 (4) |
C1—C43 | 1.381 (5) | C19—H19 | 0.9300 |
C1—H1 | 0.9300 | C20—C46 | 1.378 (5) |
C2—C35 | 1.372 (6) | C20—C21 | 1.391 (5) |
C2—C36 | 1.382 (6) | C20—H20 | 0.9300 |
C2—H2A | 0.9300 | C21—C31 | 1.358 (6) |
C3—C44 | 1.360 (5) | C21—H21 | 0.9300 |
C3—C8 | 1.387 (5) | C22—C46 | 1.385 (4) |
C3—H3 | 0.9300 | C22—C23 | 1.390 (5) |
C4—C44 | 1.366 (6) | C22—H22 | 0.9300 |
C4—C19 | 1.385 (5) | C23—C31 | 1.365 (6) |
C4—H4 | 0.9300 | C23—H23 | 0.9300 |
C5—C17 | 1.373 (6) | C24—C26 | 1.385 (6) |
C5—C40 | 1.387 (5) | C24—C35 | 1.393 (6) |
C5—H5 | 0.9300 | C25—C28 | 1.353 (11) |
C6—C39 | 1.374 (5) | C25—C27 | 1.363 (10) |
C6—C37 | 1.382 (5) | C25—H25 | 0.9300 |
C6—H6 | 0.9300 | C26—C32 | 1.334 (9) |
C7—C41 | 1.350 (5) | C26—H26 | 0.9300 |
C7—C9 | 1.364 (6) | C27—H27 | 0.9300 |
C7—H7 | 0.9300 | C28—H28 | 0.9300 |
C8—C45 | 1.393 (4) | C29—H29 | 0.9300 |
C8—H8 | 0.9300 | C30—C35 | 1.487 (5) |
C9—C10 | 1.335 (6) | C31—H31 | 0.9300 |
C9—H9 | 0.9300 | C32—C36 | 1.393 (8) |
C10—C29 | 1.348 (7) | C32—H32 | 0.9300 |
C10—H10 | 0.9300 | C36—H36 | 0.9300 |
C11—C43 | 1.380 (5) | C37—H37 | 0.9300 |
C11—C27 | 1.397 (7) | C38—H38 | 0.9300 |
C11—H11 | 0.9300 | C39—H39 | 0.9300 |
C12—C41 | 1.369 (5) | C42—H42 | 0.9300 |
C12—C29 | 1.387 (6) | C44—H44 | 0.9300 |
C45—Sn1—O1 | 101.83 (11) | C46—C20—H20 | 119.5 |
C45—Sn1—C46 | 123.43 (12) | C21—C20—H20 | 119.5 |
O1—Sn1—C46 | 95.55 (11) | C31—C21—C20 | 120.0 (4) |
C45—Sn1—C43 | 114.36 (12) | C31—C21—H21 | 120.0 |
O1—Sn1—C43 | 88.45 (11) | C20—C21—H21 | 120.0 |
C46—Sn1—C43 | 119.57 (13) | C46—C22—C23 | 120.9 (4) |
C45—Sn1—O4 | 84.32 (9) | C46—C22—H22 | 119.6 |
O1—Sn1—O4 | 171.65 (9) | C23—C22—H22 | 119.6 |
C46—Sn1—O4 | 85.56 (10) | C31—C23—C22 | 119.8 (4) |
C43—Sn1—O4 | 83.82 (11) | C31—C23—H23 | 120.1 |
O4—P1—C14 | 111.35 (14) | C22—C23—H23 | 120.1 |
O4—P1—C41 | 112.40 (14) | O2—C24—C26 | 118.2 (5) |
C14—P1—C41 | 106.59 (15) | O2—C24—C35 | 122.0 (4) |
O4—P1—C40 | 111.79 (13) | C26—C24—C35 | 119.8 (5) |
C14—P1—C40 | 106.75 (14) | C28—C25—C27 | 120.8 (6) |
C41—P1—C40 | 107.63 (15) | C28—C25—H25 | 119.6 |
C30—O1—Sn1 | 117.4 (2) | C27—C25—H25 | 119.6 |
C24—O2—H2 | 109.5 | C32—C26—C24 | 119.9 (5) |
P1—O4—Sn1 | 164.85 (13) | C32—C26—H26 | 120.1 |
C28—C1—C43 | 120.6 (5) | C24—C26—H26 | 120.1 |
C28—C1—H1 | 119.7 | C25—C27—C11 | 119.6 (6) |
C43—C1—H1 | 119.7 | C25—C27—H27 | 120.2 |
C35—C2—C36 | 121.0 (5) | C11—C27—H27 | 120.2 |
C35—C2—H2A | 119.5 | C25—C28—C1 | 120.1 (6) |
C36—C2—H2A | 119.5 | C25—C28—H28 | 119.9 |
C44—C3—C8 | 120.8 (4) | C1—C28—H28 | 119.9 |
C44—C3—H3 | 119.6 | C10—C29—C12 | 120.5 (4) |
C8—C3—H3 | 119.6 | C10—C29—H29 | 119.7 |
C44—C4—C19 | 120.5 (4) | C12—C29—H29 | 119.7 |
C44—C4—H4 | 119.7 | O5—C30—O1 | 122.7 (3) |
C19—C4—H4 | 119.7 | O5—C30—C35 | 120.9 (3) |
C17—C5—C40 | 120.3 (4) | O1—C30—C35 | 116.4 (3) |
C17—C5—H5 | 119.8 | C21—C31—C23 | 120.5 (4) |
C40—C5—H5 | 119.8 | C21—C31—H31 | 119.8 |
C39—C6—C37 | 119.7 (4) | C23—C31—H31 | 119.8 |
C39—C6—H6 | 120.1 | C26—C32—C36 | 122.1 (5) |
C37—C6—H6 | 120.1 | C26—C32—H32 | 118.9 |
C41—C7—C9 | 121.9 (4) | C36—C32—H32 | 118.9 |
C41—C7—H7 | 119.0 | C2—C35—C24 | 119.2 (4) |
C9—C7—H7 | 119.0 | C2—C35—C30 | 121.4 (4) |
C3—C8—C45 | 119.9 (3) | C24—C35—C30 | 119.4 (4) |
C3—C8—H8 | 120.0 | C2—C36—C32 | 117.9 (6) |
C45—C8—H8 | 120.0 | C2—C36—H36 | 121.0 |
C10—C9—C7 | 121.0 (4) | C32—C36—H36 | 121.0 |
C10—C9—H9 | 119.5 | C14—C37—C6 | 120.7 (3) |
C7—C9—H9 | 119.5 | C14—C37—H37 | 119.7 |
C9—C10—C29 | 118.8 (4) | C6—C37—H37 | 119.7 |
C9—C10—H10 | 120.6 | C13—C38—C14 | 120.2 (3) |
C29—C10—H10 | 120.6 | C13—C38—H38 | 119.9 |
C43—C11—C27 | 120.2 (5) | C14—C38—H38 | 119.9 |
C43—C11—H11 | 119.9 | C13—C39—C6 | 119.9 (3) |
C27—C11—H11 | 119.9 | C13—C39—H39 | 120.0 |
C41—C12—C29 | 120.5 (4) | C6—C39—H39 | 120.0 |
C41—C12—H12 | 119.8 | C15—C40—C5 | 118.2 (3) |
C29—C12—H12 | 119.8 | C15—C40—P1 | 119.1 (2) |
C39—C13—C38 | 120.7 (4) | C5—C40—P1 | 122.7 (3) |
C39—C13—H13 | 119.6 | C7—C41—C12 | 117.1 (4) |
C38—C13—H13 | 119.6 | C7—C41—P1 | 119.4 (3) |
C37—C14—C38 | 118.7 (3) | C12—C41—P1 | 123.5 (3) |
C37—C14—P1 | 118.3 (2) | C16—C42—C17 | 120.3 (4) |
C38—C14—P1 | 122.8 (3) | C16—C42—H42 | 119.8 |
C40—C15—C16 | 121.4 (4) | C17—C42—H42 | 119.8 |
C40—C15—H15 | 119.3 | C11—C43—C1 | 118.7 (4) |
C16—C15—H15 | 119.3 | C11—C43—Sn1 | 121.9 (3) |
C42—C16—C15 | 119.3 (4) | C1—C43—Sn1 | 119.4 (3) |
C42—C16—H16 | 120.3 | C3—C44—C4 | 119.6 (4) |
C15—C16—H16 | 120.3 | C3—C44—H44 | 120.2 |
C42—C17—C5 | 120.5 (5) | C4—C44—H44 | 120.2 |
C42—C17—H17 | 119.8 | C19—C45—C8 | 118.5 (3) |
C5—C17—H17 | 119.8 | C19—C45—Sn1 | 118.8 (2) |
C45—C19—C4 | 120.6 (3) | C8—C45—Sn1 | 122.6 (2) |
C45—C19—H19 | 119.7 | C20—C46—C22 | 118.0 (3) |
C4—C19—H19 | 119.7 | C20—C46—Sn1 | 122.7 (2) |
C46—C20—C21 | 121.0 (4) | C22—C46—Sn1 | 119.3 (2) |
C14—P1—O4—Sn1 | 178.5 (5) | P1—C14—C37—C6 | 175.1 (3) |
C41—P1—O4—Sn1 | −61.9 (6) | C39—C6—C37—C14 | 0.7 (6) |
C40—P1—O4—Sn1 | 59.2 (5) | C39—C13—C38—C14 | 0.5 (6) |
C44—C3—C8—C45 | −1.4 (5) | C37—C14—C38—C13 | 0.1 (5) |
C41—C7—C9—C10 | 1.0 (9) | P1—C14—C38—C13 | −175.5 (3) |
C7—C9—C10—C29 | −2.3 (9) | C38—C13—C39—C6 | −0.5 (6) |
O4—P1—C14—C37 | 28.6 (3) | C37—C6—C39—C13 | −0.1 (7) |
C41—P1—C14—C37 | −94.4 (3) | C16—C15—C40—C5 | −1.4 (6) |
C40—P1—C14—C37 | 150.8 (3) | C16—C15—C40—P1 | 176.7 (3) |
O4—P1—C14—C38 | −155.8 (3) | C17—C5—C40—C15 | 1.8 (6) |
C41—P1—C14—C38 | 81.3 (3) | C17—C5—C40—P1 | −176.2 (4) |
C40—P1—C14—C38 | −33.5 (3) | O4—P1—C40—C15 | 32.3 (3) |
C40—C15—C16—C42 | 0.3 (7) | C14—P1—C40—C15 | −89.7 (3) |
C40—C5—C17—C42 | −1.2 (8) | C41—P1—C40—C15 | 156.2 (3) |
C44—C4—C19—C45 | −0.9 (6) | O4—P1—C40—C5 | −149.8 (3) |
C46—C20—C21—C31 | −0.7 (5) | C14—P1—C40—C5 | 88.3 (3) |
C46—C22—C23—C31 | −0.5 (6) | C41—P1—C40—C5 | −25.9 (4) |
O2—C24—C26—C32 | −179.1 (5) | C9—C7—C41—C12 | 0.0 (7) |
C35—C24—C26—C32 | −0.4 (8) | C9—C7—C41—P1 | 179.3 (4) |
C28—C25—C27—C11 | 2.2 (10) | C29—C12—C41—C7 | 0.5 (8) |
C43—C11—C27—C25 | −0.9 (7) | C29—C12—C41—P1 | −178.9 (5) |
C27—C25—C28—C1 | −2.0 (10) | O4—P1—C41—C7 | 35.5 (4) |
C43—C1—C28—C25 | 0.6 (8) | C14—P1—C41—C7 | 157.7 (3) |
C9—C10—C29—C12 | 2.7 (10) | C40—P1—C41—C7 | −88.0 (4) |
C41—C12—C29—C10 | −1.8 (10) | O4—P1—C41—C12 | −145.2 (4) |
Sn1—O1—C30—O5 | −2.7 (4) | C14—P1—C41—C12 | −22.9 (4) |
Sn1—O1—C30—C35 | 176.1 (2) | C40—P1—C41—C12 | 91.3 (4) |
C20—C21—C31—C23 | 1.0 (6) | C15—C16—C42—C17 | 0.3 (8) |
C22—C23—C31—C21 | −0.4 (6) | C5—C17—C42—C16 | 0.2 (9) |
C24—C26—C32—C36 | −1.0 (9) | C27—C11—C43—C1 | −0.5 (6) |
C36—C2—C35—C24 | −0.2 (6) | C27—C11—C43—Sn1 | 179.4 (3) |
C36—C2—C35—C30 | 178.3 (4) | C28—C1—C43—C11 | 0.6 (6) |
O2—C24—C35—C2 | 179.6 (4) | C28—C1—C43—Sn1 | −179.3 (3) |
C26—C24—C35—C2 | 0.9 (6) | C8—C3—C44—C4 | −0.2 (6) |
O2—C24—C35—C30 | 1.0 (6) | C19—C4—C44—C3 | 1.3 (6) |
C26—C24—C35—C30 | −177.6 (4) | C4—C19—C45—C8 | −0.8 (5) |
O5—C30—C35—C2 | 175.1 (3) | C4—C19—C45—Sn1 | 174.7 (3) |
O1—C30—C35—C2 | −3.7 (5) | C3—C8—C45—C19 | 1.9 (5) |
O5—C30—C35—C24 | −6.3 (5) | C3—C8—C45—Sn1 | −173.4 (3) |
O1—C30—C35—C24 | 174.8 (3) | C21—C20—C46—C22 | −0.1 (5) |
C35—C2—C36—C32 | −1.1 (8) | C21—C20—C46—Sn1 | −178.4 (3) |
C26—C32—C36—C2 | 1.8 (10) | C23—C22—C46—C20 | 0.7 (5) |
C38—C14—C37—C6 | −0.7 (6) | C23—C22—C46—Sn1 | 179.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O5 | 0.82 | 1.82 | 2.546 (4) | 147 |
C8—H8···O5 | 0.93 | 2.43 | 3.071 (4) | 126 |
Acknowledgements
The authors acknowledge the Cheikh Anta Diop University (Dakar, Sénégal) for financial support. The RS2E (French Network on Electrochemical Energy Storage) and ANR (Labex STORE-EX: grant ANR-10-LABX-0076) are acknowledged for funding of the X-ray diffractometer. The authors acknowledge Dr A. G. Oliver (University of Notre Dame, USA) for his help.
References
Bandoli, G., Bortolozzo, G., Clemente, D. A., Croatto, U. & Panattoni, C. (1970). J. Chem. Soc. A, pp. 2778–2780. CSD CrossRef Web of Science Google Scholar
Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Diop, C. A. K., Touré, A., Diop, L. & Welter, R. (2006). Acta Cryst. E62, m3338–m3340. Web of Science CSD CrossRef IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ma, C., Sun, J. & Zhang, R. (2006). J. Organomet. Chem. 691, 5873–5886. CSD CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Omae, I. (1989). Organotin Chemistry (Journal of Organometallic Chemistry Library), p. 21. Amsterdam: Elsevier. Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Rauf, M. K., Saeed, M. A., Din, I.-U., Bolte, M., Badshah, A. & Mirza, B. (2008). J. Organomet. Chem. 693, 3043–3048. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Vollano, J. F., Day, R. O., Rau, D. N., Chandrasekhar, V. & Holmes, R. R. (1984). Inorg. Chem. 23, 3153–3160. CSD CrossRef CAS Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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