metal-organic compounds
Dibutylammonium bis(hydrogen methylphosphonato-κO)triphenylstannate(IV)
aLaboratoire de Chimie Minerale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, bLaboratoire de Chimie Organique et Therapeutique, Département de Pharmacie, Faculté de Medecine, de Pharmacie et d'Odontostomatologie, Université Cheikh Anta Diop, Dakar, Senegal, and cInstitut Européen des Membranes, Université de Montpellier II, 34000 Montpellier, France
*Correspondence e-mail: tijchimia@yahoo.fr
The 8H20N)[Sn(C6H5)3(CH4O3P)2], contains two dibutylammonium cations and two stannate(IV) anions consisting each of two monodentately bonding methyl hydrogenphosphate groups attached to an Sn(C6H5) unit. The overall coordination environment of the two SnIV atoms is trigonal–bipyramidal defined by three phenyl C atoms in equatorial positions and two methyl hydrogenphosphate O atoms at the apical sites. In the crystal, the stannate(IV) anions are linked to each other via pairs of short O—H⋯O hydrogen bonds, leading to an infinite chain extending parallel to the b-axis direction. Neighbouring chains are linked by N—H⋯O hydrogen bonds involving the butylammonium cations, giving a two-dimensional structure parallel to the ab plane. The crystal under investigation was found to be twinned by reticular with twin fractions of 0.5342 (7):0.4658 (7).
of the title organotin salt, (CRelated literature
For general background to and applications of tin(IV) compounds, see: Davies et al. (2008); Gielen (2002); Molloy et al. (1984). For related structures, see: Adair et al. (2003); Chunlin et al. (2008); Diop et al. (2002, 2011); Gueye et al. (2011); Sow et al. (2012). For details of the use of constraints and restraints during the structure see: Cooper et al. (2010). For background to the weighting schemes used in the see: Prince (1982); Watkin (1994).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrysAlis PRO (Agilent, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: CRYSTALS and publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536812038445/wm2676sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038445/wm2676Isup2.hkl
An ethanolic solution containing 0.30 g (1.20 mmol) of Bu2NH2MePO3H (obtained from an aqueous mixture of dibutylamine and MeP(O)(OH)2 in water in a 1:1 ratio) and triphenyltin(IV) chloride (SnPh3Cl) 2.25 g (0.66 mmol) was stirred at room temperature for more than one hour. After 96 h of slow evaporation of the solution, colourless crystals of the title compound (yield: 78%; m.p: 250°) suitable for X-ray
were obtained within the remaining solvent. The powder obtained after complete solvent evaporation has the formula Bu2NH2Cl according to its infrared spectrum.H atoms were all located in a difference Fourier map, but those attached to C atoms were repositioned geometrically. They were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H bond lengths in the range 0.93–0.98 Å, N—H bond length 0.89 Å, O—H bond length 0.85 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints (Cooper et al., 2010).
The large diplacement ellipsoids and deviating C—C distances of the dibutylammonium cations indicated slight displacement disorder, which, however could not be resolved in difference Fourier maps. The dibutylammonium cations were therefore regularized and refined with soft distance and angle restraints.
The crystal under investigation was found to be twinned by reticular
with 7 and twin fractions 0.5342 (7) and 0.4658 (7). The twin is a twofold rotation axis along the reciprocal c* axis; the pseudo-orthorhombic lattice can be generated by a' = a, b' = b, c' = 7c - a.Organotin(IV) complexes are extensively studied due to their industrial applications as well as for their biocidal properties (Molloy et al., 1984; Gielen, 2002; Davies et al., 2008). Our group has conducted research on SnMe3 and SnPh3 residues containing derivatives with mono- and polybasic oxyanions such as C2O42- (Gueye et al., 2011; Sow et al., 2012) and PhP(H)O2- (Diop et al., 2011). Here we report the structure of the title compound, [(C4H9)2NH2]+[Sn(C6H5)3(CH3PO2OH)2]-, (I).
The
of compound (I) is illustrated in Fig. 1. It consists of two dibutylammonium cations and two organotin complexes consisting of two monodentate MePO3H- anions bonded to SnPh3; the SnIV atoms exhibit a trans trigonal bipyramidal coordination environment consisting of three phenyl carbon atoms and two MePO3H- oxygen atoms. The trigonal plane of the Sn atoms is defined by the three phenyl groups whereas the axial positions are occupied by oxygen atoms from the methyl hydrogenphosphate tetrahedra. A similar arrangement around tin(IV) has been observed in the of {[(CH3)3Sn]4(O3PPh)2}n (Chunlin et al., 2008). The sums of the angles at the tin(IV) positions by the ipso-carbons atoms [119.9 (2)°, 121.2 (2)°, 118.8 (2)°, and 122.4 (2)°, 119.0 (2)° and 118.6 (2)° for the two SnIV entities] are 359.9° and 360.0°, respectively; the corresponding axial O101—Sn1—O106 and O201—Sn2—O206 angles are 174.71 (14)° and 174.15 (14)°, respectively, indicating a nearly perfect trans trigonal bipyramidal arrangement. The Sn—C bond lengths are almost identical within the experimental error (Sn1—C111: 2.128 (6) Å; Sn1—C117: 2.137 (6) Å; Sn1—C123 2.125 (5) Å; Sn2—C211: 2.125 (6) Å; Sn2—C217: 2.126 (6) Å; Sn2—C223 2.134 (6) Å] and lie in the range reported for related structures (Gueye et al., 2011). The two axial Sn—O distances, [Sn1—O101 2.175 (4) Å; Sn1—O106 2.188 (3) Å; Sn2—O201 2.188 (3) Å; Sn2—O206 2.169 (4) Å] are in the range of axial Sn—O distances (2.165 (4) and 2.434 (4) Å) observed in catena-trimethyltin(IV) methylphosphonate, [MePO3HSnMe3] (Diop et al., 2002), but are longer than the axial Sn—O distances [2.116 (2) Å and 2.132 (3) Å] observed in catena-(µ2-phenylphosphinato O, O')-chlorido-tin(II) (Adair et al., 2003). The geometry at the P sites is a distorted tetrahedron with bond angles ranging from 102.7 (3)° for O208—P207—C210 to 114.2 (2) for O201—P202—O204.The stannate(IV) anions [(MePO3H)2SnPh3]- are linked by pairs of short O—H···O hydrogen bonds, involving the hydroxy group of the methyl hydrogenphosphate unit, and thus forming an infinite chain (Table 1, Fig. 2) along the b-direction. In the crystal, neighbouring chains are linked by N—H···O hydrogen bonds via the Bu2NH2+ cations, forming a supramolecular structure parallel to the ab plane.
For general background to and applications of tin(IV) compounds, see: Davies et al. (2008); Gielen (2002); Molloy et al. (1984). For related structures, see: Adair et al. (2003); Chunlin et al. (2008); Diop et al. (2002, 2011); Gueye et al. (2011); Sow et al. (2012). For details of the use of constraints and restraints during the
see: Cooper et al. (2010). For background to the weighting schemes used in the see: Prince (1982); Watkin (1994).Data collection: CrysAlis PRO (Agilent, 2010); cell
CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003) and publCIF (Westrip, 2010).Fig. 1. The two pairs of molecular entities in the title compound with anisotropic displacement parameters drawn at the 30% probability level. H atoms are shown as spheres of arbitary radius. | |
Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. |
(C8H20N)[Sn(C6H5)3(CH4O3P)2] | F(000) = 2768 |
Mr = 670.28 | Dx = 1.374 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7455 reflections |
a = 16.1963 (8) Å | θ = 1.4–29.2° |
b = 18.9088 (8) Å | µ = 0.93 mm−1 |
c = 21.1989 (11) Å | T = 175 K |
β = 93.220 (4)° | Block, colourless |
V = 6482.0 (5) Å3 | 0.30 × 0.25 × 0.10 mm |
Z = 8 |
Oxford Diffraction Gemini diffractometer | 17225 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.085 |
ω scans | θmax = 29.2°, θmin = 1.4° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | h = −20→22 |
Tmin = 0.961, Tmax = 1.000 | k = −24→24 |
64843 measured reflections | l = −28→27 |
26060 independent reflections |
Refinement on F | Primary atom site location: charge-flipping |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.067 | Method, part 1, Chebychev polynomial, (Watkin, 1994; Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 15.1 4.23 12.3 3.23 |
S = 0.99 | (Δ/σ)max = 0.003 |
17225 reflections | Δρmax = 1.28 e Å−3 |
686 parameters | Δρmin = −1.66 e Å−3 |
9 restraints |
(C8H20N)[Sn(C6H5)3(CH4O3P)2] | V = 6482.0 (5) Å3 |
Mr = 670.28 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.1963 (8) Å | µ = 0.93 mm−1 |
b = 18.9088 (8) Å | T = 175 K |
c = 21.1989 (11) Å | 0.30 × 0.25 × 0.10 mm |
β = 93.220 (4)° |
Oxford Diffraction Gemini diffractometer | 26060 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | 17225 reflections with I > 2.0σ(I) |
Tmin = 0.961, Tmax = 1.000 | Rint = 0.085 |
64843 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 9 restraints |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 0.99 | Δρmax = 1.28 e Å−3 |
17225 reflections | Δρmin = −1.66 e Å−3 |
686 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.55169 (2) | 0.19275 (2) | 0.195941 (16) | 0.0285 | |
O101 | 0.5156 (3) | 0.3004 (2) | 0.21763 (18) | 0.0413 | |
P102 | 0.49515 (8) | 0.37108 (7) | 0.18772 (7) | 0.0296 | |
O103 | 0.4023 (2) | 0.3900 (2) | 0.1956 (2) | 0.0506 | |
H1031 | 0.3906 | 0.4158 | 0.2267 | 0.0600* | |
O104 | 0.5479 (2) | 0.4314 (2) | 0.2139 (2) | 0.0440 | |
C105 | 0.5019 (5) | 0.3644 (4) | 0.1041 (3) | 0.0534 | |
H1051 | 0.4684 | 0.3265 | 0.0876 | 0.0664* | |
H1052 | 0.4828 | 0.4075 | 0.0840 | 0.0664* | |
H1053 | 0.5576 | 0.3566 | 0.0936 | 0.0664* | |
O106 | 0.5926 (2) | 0.08826 (17) | 0.16616 (18) | 0.0316 | |
P107 | 0.57266 (8) | 0.01052 (7) | 0.16887 (7) | 0.0296 | |
O108 | 0.4833 (2) | 0.0013 (2) | 0.1908 (2) | 0.0506 | |
H1081 | 0.4726 | −0.0226 | 0.2233 | 0.0601* | |
O109 | 0.6335 (2) | −0.03205 (18) | 0.20970 (19) | 0.0335 | |
C110 | 0.5695 (4) | −0.0236 (4) | 0.0899 (3) | 0.0528 | |
H1101 | 0.5316 | 0.0027 | 0.0631 | 0.1230* | |
H1102 | 0.5532 | −0.0721 | 0.0893 | 0.1230* | |
H1103 | 0.6233 | −0.0204 | 0.0731 | 0.1230* | |
C111 | 0.4357 (3) | 0.1784 (3) | 0.1454 (3) | 0.0360 | |
C112 | 0.3649 (4) | 0.2063 (3) | 0.1685 (3) | 0.0410 | |
H1121 | 0.3669 | 0.2318 | 0.2059 | 0.0493* | |
C113 | 0.2880 (3) | 0.1965 (4) | 0.1360 (4) | 0.0557 | |
H1131 | 0.2405 | 0.2156 | 0.1530 | 0.0669* | |
C114 | 0.2816 (5) | 0.1595 (4) | 0.0803 (4) | 0.0654 | |
H1141 | 0.2309 | 0.1530 | 0.0589 | 0.0784* | |
C115 | 0.3523 (4) | 0.1322 (4) | 0.0560 (4) | 0.0552 | |
H1151 | 0.3485 | 0.1083 | 0.0178 | 0.0671* | |
C116 | 0.4285 (4) | 0.1411 (3) | 0.0886 (3) | 0.0433 | |
H1161 | 0.4763 | 0.1224 | 0.0724 | 0.0510* | |
C117 | 0.5635 (3) | 0.1714 (3) | 0.2950 (3) | 0.0332 | |
C118 | 0.5865 (3) | 0.1055 (3) | 0.3186 (3) | 0.0399 | |
H1181 | 0.5968 | 0.0690 | 0.2910 | 0.0475* | |
C119 | 0.5950 (4) | 0.0922 (4) | 0.3827 (3) | 0.0500 | |
H1191 | 0.6097 | 0.0472 | 0.3970 | 0.0600* | |
C120 | 0.5810 (5) | 0.1433 (4) | 0.4247 (3) | 0.0580 | |
H1201 | 0.5858 | 0.1340 | 0.4680 | 0.0721* | |
C121 | 0.5580 (5) | 0.2094 (5) | 0.4041 (3) | 0.0633 | |
H1211 | 0.5471 | 0.2444 | 0.4337 | 0.0761* | |
C122 | 0.5503 (5) | 0.2239 (3) | 0.3389 (3) | 0.0527 | |
H1221 | 0.5360 | 0.2685 | 0.3252 | 0.0635* | |
C123 | 0.6561 (3) | 0.2318 (3) | 0.1505 (3) | 0.0328 | |
C124 | 0.7102 (4) | 0.2768 (3) | 0.1807 (3) | 0.0492 | |
H1241 | 0.7007 | 0.2909 | 0.2218 | 0.0591* | |
C125 | 0.7801 (4) | 0.3024 (4) | 0.1519 (4) | 0.0679 | |
H1251 | 0.8163 | 0.3331 | 0.1729 | 0.0821* | |
C126 | 0.7936 (5) | 0.2831 (4) | 0.0917 (4) | 0.0686 | |
H1261 | 0.8414 | 0.2987 | 0.0728 | 0.0820* | |
C127 | 0.7387 (5) | 0.2393 (4) | 0.0596 (4) | 0.0666 | |
H1271 | 0.7466 | 0.2268 | 0.0181 | 0.0781* | |
C128 | 0.6701 (4) | 0.2132 (4) | 0.0889 (3) | 0.0501 | |
H1281 | 0.6333 | 0.1824 | 0.0671 | 0.0591* | |
Sn2 | 1.06366 (2) | 0.19358 (2) | 0.300170 (16) | 0.0299 | |
O201 | 1.1082 (2) | 0.09045 (18) | 0.33422 (18) | 0.0329 | |
P202 | 1.08457 (8) | 0.01320 (7) | 0.33239 (7) | 0.0311 | |
O203 | 0.9928 (2) | 0.0086 (3) | 0.3079 (3) | 0.0602 | |
H2031 | 0.9764 | −0.0176 | 0.2771 | 0.0723* | |
O204 | 1.1394 (2) | −0.03227 (18) | 0.29425 (19) | 0.0328 | |
C205 | 1.0875 (5) | −0.0203 (4) | 0.4117 (4) | 0.0628 | |
H2051 | 1.0734 | −0.0692 | 0.4117 | 0.0705* | |
H2052 | 1.0505 | 0.0052 | 0.4364 | 0.0705* | |
H2053 | 1.1426 | −0.0154 | 0.4310 | 0.0705* | |
O206 | 1.0252 (3) | 0.3003 (2) | 0.27527 (19) | 0.0446 | |
P207 | 1.00599 (8) | 0.37021 (7) | 0.30592 (7) | 0.0324 | |
O208 | 0.9118 (2) | 0.3870 (3) | 0.2967 (3) | 0.0565 | |
H2081 | 0.8950 | 0.4139 | 0.2665 | 0.0666* | |
O209 | 1.0549 (2) | 0.4318 (2) | 0.2817 (2) | 0.0404 | |
C210 | 1.0210 (5) | 0.3624 (4) | 0.3897 (3) | 0.0559 | |
H2101 | 0.9901 | 0.3235 | 0.4048 | 0.0675* | |
H2102 | 1.0781 | 0.3551 | 0.4017 | 0.0675* | |
H2103 | 1.0031 | 0.4046 | 0.4098 | 0.0675* | |
C211 | 0.9552 (4) | 0.1822 (3) | 0.3512 (3) | 0.0373 | |
C212 | 0.8793 (3) | 0.2069 (3) | 0.3260 (3) | 0.0379 | |
H2121 | 0.8748 | 0.2289 | 0.2863 | 0.0451* | |
C213 | 0.8088 (4) | 0.1984 (4) | 0.3591 (4) | 0.0554 | |
H2131 | 0.7593 | 0.2165 | 0.3424 | 0.0659* | |
C214 | 0.8108 (5) | 0.1656 (4) | 0.4158 (4) | 0.0629 | |
H2141 | 0.7629 | 0.1588 | 0.4365 | 0.0745* | |
C215 | 0.8862 (5) | 0.1414 (4) | 0.4430 (4) | 0.0648 | |
H2151 | 0.8881 | 0.1205 | 0.4829 | 0.0768* | |
C216 | 0.9571 (5) | 0.1492 (3) | 0.4095 (3) | 0.0501 | |
H2161 | 1.0075 | 0.1329 | 0.4269 | 0.0593* | |
C217 | 1.1762 (3) | 0.2337 (3) | 0.3424 (3) | 0.0338 | |
C218 | 1.2274 (4) | 0.2774 (4) | 0.3092 (4) | 0.0561 | |
H2181 | 1.2114 | 0.2898 | 0.2682 | 0.0670* | |
C219 | 1.3013 (5) | 0.3022 (5) | 0.3362 (5) | 0.0772 | |
H2191 | 1.3342 | 0.3318 | 0.3134 | 0.0910* | |
C220 | 1.3251 (5) | 0.2840 (4) | 0.3964 (4) | 0.0646 | |
H2201 | 1.3753 | 0.3008 | 0.4135 | 0.0769* | |
C221 | 1.2774 (5) | 0.2419 (4) | 0.4310 (4) | 0.0656 | |
H2211 | 1.2948 | 0.2297 | 0.4724 | 0.0781* | |
C222 | 1.2018 (4) | 0.2164 (4) | 0.4036 (3) | 0.0508 | |
H2221 | 1.1688 | 0.1878 | 0.4277 | 0.0594* | |
C223 | 1.0585 (3) | 0.1674 (3) | 0.2021 (3) | 0.0353 | |
C224 | 1.0816 (4) | 0.1013 (3) | 0.1805 (3) | 0.0437 | |
H2241 | 1.0993 | 0.0676 | 0.2094 | 0.0522* | |
C225 | 1.0786 (4) | 0.0854 (4) | 0.1166 (3) | 0.0519 | |
H2251 | 1.0967 | 0.0416 | 0.1033 | 0.0613* | |
C226 | 1.0495 (4) | 0.1335 (4) | 0.0728 (3) | 0.0592 | |
H2261 | 1.0446 | 0.1227 | 0.0298 | 0.0711* | |
C227 | 1.0266 (6) | 0.1998 (5) | 0.0932 (3) | 0.0733 | |
H2271 | 1.0096 | 0.2344 | 0.0636 | 0.0861* | |
C228 | 1.0293 (5) | 0.2172 (4) | 0.1571 (3) | 0.0586 | |
H2281 | 1.0113 | 0.2609 | 0.1702 | 0.0690* | |
N10 | 0.7984 (3) | 0.0021 (3) | 0.2374 (2) | 0.0397 | |
H101 | 0.8398 | −0.0259 | 0.2269 | 0.0581* | |
H102 | 0.7505 | −0.0165 | 0.2220 | 0.0580* | |
C11 | 0.8098 (4) | 0.0735 (4) | 0.2092 (4) | 0.0590 | |
H111 | 0.8509 | 0.0989 | 0.2359 | 0.0722* | |
H112 | 0.7582 | 0.0986 | 0.2090 | 0.0721* | |
C12 | 0.8419 (7) | 0.0707 (5) | 0.1451 (4) | 0.1010 | |
H121 | 0.8985 | 0.0577 | 0.1505 | 0.1239* | |
H122 | 0.8378 | 0.1177 | 0.1294 | 0.1239* | |
C13 | 0.8007 (6) | 0.0261 (6) | 0.0961 (4) | 0.1139 | |
H131 | 0.8020 | −0.0213 | 0.1110 | 0.1425* | |
H132 | 0.7449 | 0.0402 | 0.0875 | 0.1425* | |
C14 | 0.8478 (6) | 0.0293 (6) | 0.0368 (4) | 0.1091 | |
H141 | 0.8216 | 0.0007 | 0.0047 | 0.1306* | |
H142 | 0.9025 | 0.0127 | 0.0461 | 0.1306* | |
H143 | 0.8496 | 0.0769 | 0.0227 | 0.1306* | |
C15 | 0.7993 (4) | 0.0052 (5) | 0.3066 (3) | 0.0659 | |
H151 | 0.7482 | 0.0280 | 0.3176 | 0.0786* | |
H152 | 0.8468 | 0.0330 | 0.3227 | 0.0791* | |
C16 | 0.8015 (4) | −0.0687 (5) | 0.3348 (3) | 0.0731 | |
H161 | 0.7513 | −0.0929 | 0.3200 | 0.0892* | |
H162 | 0.8479 | −0.0928 | 0.3187 | 0.0889* | |
C17 | 0.8065 (9) | −0.0572 (6) | 0.4059 (4) | 0.1531 | |
H171 | 0.8527 | −0.0278 | 0.4170 | 0.1878* | |
H172 | 0.7574 | −0.0350 | 0.4182 | 0.1878* | |
C18 | 0.8169 (12) | −0.1248 (8) | 0.4378 (5) | 0.2082 | |
H181 | 0.8202 | −0.1166 | 0.4821 | 0.2303* | |
H182 | 0.8661 | −0.1472 | 0.4259 | 0.2303* | |
H183 | 0.7708 | −0.1544 | 0.4271 | 0.2303* | |
N20 | 0.6997 (2) | 0.4947 (2) | 0.2381 (2) | 0.0309 | |
H201 | 0.7428 | 0.4776 | 0.2187 | 0.0458* | |
H202 | 0.6542 | 0.4700 | 0.2261 | 0.0463* | |
C21 | 0.6841 (4) | 0.5698 (3) | 0.2174 (3) | 0.0445 | |
H211 | 0.7364 | 0.5941 | 0.2176 | 0.0532* | |
H212 | 0.6498 | 0.5929 | 0.2471 | 0.0532* | |
C22 | 0.6400 (4) | 0.5728 (4) | 0.1526 (3) | 0.0603 | |
H221 | 0.6343 | 0.6227 | 0.1417 | 0.0720* | |
H222 | 0.5852 | 0.5519 | 0.1544 | 0.0721* | |
C23 | 0.6829 (3) | 0.5372 (4) | 0.1006 (3) | 0.0628 | |
H231 | 0.6902 | 0.4872 | 0.1105 | 0.0753* | |
H232 | 0.7364 | 0.5591 | 0.0965 | 0.0751* | |
C24 | 0.6310 (5) | 0.5448 (5) | 0.0389 (3) | 0.0877 | |
H241 | 0.6585 | 0.5199 | 0.0063 | 0.1319* | |
H242 | 0.6246 | 0.5938 | 0.0271 | 0.1320* | |
H243 | 0.5770 | 0.5248 | 0.0428 | 0.1321* | |
C25 | 0.7138 (3) | 0.4836 (3) | 0.3079 (3) | 0.0403 | |
H251 | 0.7670 | 0.5050 | 0.3207 | 0.0479* | |
H252 | 0.6708 | 0.5084 | 0.3290 | 0.0483* | |
C26 | 0.7143 (4) | 0.4058 (3) | 0.3241 (3) | 0.0421 | |
H261 | 0.6609 | 0.3854 | 0.3110 | 0.0499* | |
H262 | 0.7570 | 0.3824 | 0.3010 | 0.0505* | |
C27 | 0.7300 (4) | 0.3921 (4) | 0.3944 (3) | 0.0555 | |
H271 | 0.7379 | 0.3418 | 0.4009 | 0.0672* | |
H272 | 0.7801 | 0.4179 | 0.4089 | 0.0672* | |
C28 | 0.6607 (5) | 0.4144 (5) | 0.4341 (4) | 0.0701 | |
H281 | 0.6113 | 0.3892 | 0.4209 | 0.1071* | |
H282 | 0.6730 | 0.4054 | 0.4786 | 0.1069* | |
H283 | 0.6516 | 0.4642 | 0.4276 | 0.1068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03063 (19) | 0.02368 (17) | 0.0318 (2) | 0.00151 (15) | 0.00695 (13) | 0.00110 (15) |
O101 | 0.057 (2) | 0.0268 (18) | 0.041 (2) | 0.0067 (18) | 0.0122 (17) | −0.0018 (17) |
P102 | 0.0247 (7) | 0.0243 (6) | 0.0398 (7) | 0.0022 (5) | 0.0031 (5) | −0.0042 (5) |
O103 | 0.0185 (19) | 0.065 (3) | 0.068 (3) | 0.0100 (17) | −0.0051 (18) | −0.036 (2) |
O104 | 0.040 (2) | 0.036 (2) | 0.057 (3) | 0.0020 (17) | 0.0118 (19) | −0.0128 (19) |
C105 | 0.072 (4) | 0.052 (4) | 0.035 (3) | 0.010 (3) | 0.002 (3) | 0.000 (3) |
O106 | 0.0303 (17) | 0.0197 (16) | 0.045 (2) | 0.0014 (14) | 0.0067 (15) | 0.0019 (15) |
P107 | 0.0235 (6) | 0.0232 (6) | 0.0423 (8) | 0.0003 (5) | 0.0040 (5) | 0.0047 (5) |
O108 | 0.028 (2) | 0.061 (3) | 0.063 (3) | 0.0038 (19) | 0.0038 (19) | 0.034 (2) |
O109 | 0.0215 (17) | 0.0274 (18) | 0.052 (2) | 0.0011 (14) | 0.0056 (16) | 0.0038 (16) |
C110 | 0.062 (4) | 0.044 (4) | 0.051 (4) | 0.005 (3) | −0.002 (3) | −0.011 (3) |
C111 | 0.034 (3) | 0.028 (3) | 0.046 (3) | −0.001 (2) | −0.001 (2) | 0.009 (2) |
C112 | 0.036 (3) | 0.029 (3) | 0.059 (4) | −0.001 (2) | 0.012 (3) | 0.004 (2) |
C113 | 0.025 (3) | 0.064 (4) | 0.078 (5) | 0.003 (3) | 0.000 (3) | 0.017 (4) |
C114 | 0.054 (4) | 0.064 (5) | 0.075 (6) | −0.014 (4) | −0.021 (4) | 0.019 (4) |
C115 | 0.050 (4) | 0.056 (4) | 0.058 (4) | 0.000 (3) | −0.011 (3) | −0.003 (3) |
C116 | 0.046 (3) | 0.039 (3) | 0.044 (3) | 0.006 (3) | 0.001 (3) | 0.006 (3) |
C117 | 0.027 (3) | 0.038 (3) | 0.035 (3) | −0.005 (2) | 0.003 (2) | −0.001 (2) |
C118 | 0.037 (3) | 0.040 (3) | 0.043 (3) | 0.004 (2) | 0.003 (2) | 0.002 (3) |
C119 | 0.046 (4) | 0.061 (4) | 0.044 (4) | 0.007 (3) | 0.006 (3) | 0.013 (3) |
C120 | 0.062 (4) | 0.080 (5) | 0.033 (3) | 0.007 (4) | 0.003 (3) | 0.010 (3) |
C121 | 0.067 (4) | 0.083 (6) | 0.040 (4) | 0.014 (4) | 0.002 (3) | −0.009 (3) |
C122 | 0.076 (5) | 0.040 (3) | 0.043 (4) | 0.007 (3) | 0.005 (3) | 0.003 (3) |
C123 | 0.039 (3) | 0.019 (2) | 0.040 (3) | 0.004 (2) | 0.006 (2) | 0.006 (2) |
C124 | 0.053 (4) | 0.042 (3) | 0.053 (4) | −0.014 (3) | 0.011 (3) | −0.013 (3) |
C125 | 0.057 (4) | 0.066 (5) | 0.082 (5) | −0.032 (4) | 0.014 (4) | −0.015 (4) |
C126 | 0.065 (4) | 0.049 (4) | 0.096 (6) | −0.027 (3) | 0.042 (4) | 0.002 (4) |
C127 | 0.081 (5) | 0.065 (5) | 0.058 (5) | −0.018 (4) | 0.039 (4) | −0.008 (4) |
C128 | 0.057 (4) | 0.054 (4) | 0.040 (3) | −0.020 (3) | 0.009 (3) | −0.008 (3) |
Sn2 | 0.03160 (19) | 0.02667 (18) | 0.0314 (2) | 0.00085 (15) | 0.00178 (13) | −0.00105 (16) |
O201 | 0.0310 (18) | 0.0242 (17) | 0.043 (2) | 0.0006 (14) | −0.0008 (15) | −0.0001 (15) |
P202 | 0.0265 (6) | 0.0241 (6) | 0.0433 (8) | −0.0018 (5) | 0.0064 (6) | −0.0043 (5) |
O203 | 0.028 (2) | 0.066 (3) | 0.087 (4) | −0.001 (2) | 0.007 (2) | −0.051 (3) |
O204 | 0.0223 (17) | 0.0257 (18) | 0.050 (2) | −0.0015 (14) | 0.0027 (16) | −0.0027 (16) |
C205 | 0.091 (6) | 0.038 (3) | 0.061 (5) | 0.011 (4) | 0.023 (4) | 0.011 (3) |
O206 | 0.063 (3) | 0.0279 (19) | 0.043 (2) | 0.0094 (19) | 0.0026 (19) | 0.0039 (17) |
P207 | 0.0268 (7) | 0.0261 (6) | 0.0444 (8) | 0.0026 (5) | 0.0034 (6) | 0.0061 (6) |
O208 | 0.029 (2) | 0.059 (3) | 0.083 (4) | 0.0078 (19) | 0.009 (2) | 0.034 (3) |
O209 | 0.034 (2) | 0.033 (2) | 0.053 (3) | −0.0015 (16) | −0.0044 (17) | 0.0153 (18) |
C210 | 0.080 (5) | 0.046 (4) | 0.041 (3) | 0.000 (3) | 0.005 (3) | −0.005 (3) |
C211 | 0.045 (3) | 0.019 (3) | 0.049 (3) | 0.001 (2) | 0.012 (3) | −0.006 (2) |
C212 | 0.031 (3) | 0.026 (3) | 0.057 (4) | 0.003 (2) | 0.005 (2) | −0.006 (2) |
C213 | 0.033 (3) | 0.043 (4) | 0.090 (6) | 0.001 (3) | 0.005 (3) | −0.016 (4) |
C214 | 0.053 (4) | 0.054 (4) | 0.087 (6) | −0.010 (3) | 0.044 (4) | −0.021 (4) |
C215 | 0.089 (6) | 0.055 (4) | 0.055 (4) | 0.002 (4) | 0.037 (4) | −0.004 (3) |
C216 | 0.058 (4) | 0.044 (3) | 0.050 (4) | 0.014 (3) | 0.016 (3) | −0.002 (3) |
C217 | 0.041 (3) | 0.018 (2) | 0.043 (3) | −0.004 (2) | 0.008 (2) | −0.003 (2) |
C218 | 0.060 (4) | 0.050 (4) | 0.058 (4) | −0.021 (3) | 0.005 (3) | 0.005 (3) |
C219 | 0.064 (5) | 0.067 (5) | 0.102 (7) | −0.031 (4) | 0.012 (4) | −0.002 (5) |
C220 | 0.054 (4) | 0.042 (4) | 0.096 (6) | −0.018 (3) | −0.014 (4) | −0.016 (4) |
C221 | 0.074 (5) | 0.056 (4) | 0.063 (5) | −0.013 (4) | −0.019 (4) | −0.009 (4) |
C222 | 0.048 (3) | 0.049 (4) | 0.054 (4) | −0.013 (3) | −0.007 (3) | 0.001 (3) |
C223 | 0.024 (3) | 0.049 (3) | 0.032 (3) | 0.001 (2) | −0.005 (2) | 0.003 (2) |
C224 | 0.047 (3) | 0.045 (3) | 0.039 (3) | 0.006 (3) | 0.008 (3) | −0.002 (3) |
C225 | 0.047 (4) | 0.064 (4) | 0.045 (4) | 0.007 (3) | 0.006 (3) | −0.013 (3) |
C226 | 0.061 (4) | 0.084 (5) | 0.032 (3) | 0.009 (4) | 0.000 (3) | −0.010 (3) |
C227 | 0.105 (6) | 0.075 (5) | 0.039 (4) | 0.021 (5) | −0.002 (4) | 0.012 (4) |
C228 | 0.083 (5) | 0.055 (4) | 0.037 (3) | 0.018 (4) | 0.000 (3) | 0.000 (3) |
N10 | 0.022 (2) | 0.050 (3) | 0.047 (3) | 0.0011 (19) | 0.0025 (19) | −0.010 (2) |
C11 | 0.037 (3) | 0.041 (4) | 0.098 (6) | −0.002 (3) | −0.005 (3) | −0.009 (4) |
C12 | 0.146 (10) | 0.053 (5) | 0.105 (9) | −0.014 (6) | 0.022 (7) | 0.025 (5) |
C13 | 0.158 (11) | 0.091 (8) | 0.092 (8) | −0.032 (8) | 0.001 (8) | 0.030 (6) |
C14 | 0.110 (8) | 0.144 (10) | 0.075 (7) | 0.041 (7) | 0.015 (6) | 0.034 (7) |
C15 | 0.032 (3) | 0.121 (7) | 0.045 (4) | 0.028 (4) | 0.004 (3) | −0.021 (4) |
C16 | 0.033 (3) | 0.135 (8) | 0.052 (4) | 0.011 (4) | 0.002 (3) | 0.021 (5) |
C17 | 0.186 (14) | 0.205 (16) | 0.073 (8) | 0.077 (12) | 0.053 (8) | 0.040 (9) |
C18 | 0.29 (3) | 0.23 (2) | 0.112 (13) | 0.098 (19) | 0.069 (14) | 0.054 (13) |
N20 | 0.0214 (19) | 0.032 (2) | 0.039 (3) | −0.0033 (16) | 0.0043 (17) | −0.0015 (18) |
C21 | 0.036 (3) | 0.034 (3) | 0.065 (4) | −0.004 (2) | 0.010 (3) | −0.001 (3) |
C22 | 0.055 (4) | 0.052 (4) | 0.075 (5) | 0.008 (3) | 0.011 (4) | 0.017 (4) |
C23 | 0.050 (4) | 0.082 (5) | 0.056 (5) | −0.013 (4) | −0.003 (3) | 0.018 (4) |
C24 | 0.081 (6) | 0.115 (8) | 0.064 (6) | −0.023 (6) | −0.017 (4) | 0.018 (5) |
C25 | 0.031 (3) | 0.052 (3) | 0.038 (3) | −0.005 (2) | 0.001 (2) | −0.005 (3) |
C26 | 0.039 (3) | 0.042 (3) | 0.045 (3) | −0.003 (2) | 0.007 (2) | −0.004 (3) |
C27 | 0.053 (4) | 0.066 (4) | 0.047 (4) | 0.010 (3) | −0.004 (3) | 0.004 (3) |
C28 | 0.082 (5) | 0.081 (5) | 0.048 (4) | 0.018 (4) | 0.015 (4) | 0.008 (4) |
Sn1—O101 | 2.175 (4) | C214—C215 | 1.398 (12) |
Sn1—O106 | 2.188 (3) | C215—H2151 | 0.933 |
Sn1—C111 | 2.128 (6) | C215—C216 | 1.391 (10) |
Sn1—C117 | 2.137 (6) | C216—H2161 | 0.930 |
Sn1—C123 | 2.125 (5) | C217—C218 | 1.390 (8) |
Sn2—O201 | 2.188 (3) | C217—C222 | 1.378 (9) |
Sn2—O206 | 2.169 (4) | C218—H2181 | 0.923 |
Sn2—C211 | 2.125 (6) | C218—C219 | 1.380 (10) |
Sn2—C217 | 2.126 (6) | C219—H2191 | 0.926 |
Sn2—C223 | 2.134 (6) | C219—C220 | 1.357 (12) |
O101—P102 | 1.507 (4) | C220—H2201 | 0.927 |
P102—O103 | 1.563 (4) | C220—C221 | 1.353 (11) |
P102—O104 | 1.511 (4) | C221—H2211 | 0.935 |
P102—C105 | 1.787 (6) | C221—C222 | 1.410 (9) |
O103—H1031 | 0.850 | C222—H2221 | 0.933 |
C105—H1051 | 0.953 | C223—C224 | 1.388 (8) |
C105—H1052 | 0.962 | C223—C228 | 1.405 (9) |
C105—H1053 | 0.953 | C224—H2241 | 0.920 |
O106—P107 | 1.507 (3) | C224—C225 | 1.384 (9) |
P107—O108 | 1.554 (4) | C225—H2251 | 0.929 |
P107—O109 | 1.508 (4) | C225—C226 | 1.365 (10) |
P107—C110 | 1.793 (7) | C226—H2261 | 0.933 |
O108—H1081 | 0.850 | C226—C227 | 1.384 (11) |
C110—H1101 | 0.951 | C227—H2271 | 0.937 |
C110—H1102 | 0.954 | C227—C228 | 1.393 (10) |
C110—H1103 | 0.963 | C228—H2281 | 0.924 |
C111—C112 | 1.376 (8) | N10—H101 | 0.893 |
C111—C116 | 1.395 (9) | N10—H102 | 0.896 |
C112—H1121 | 0.927 | N10—C11 | 1.493 (9) |
C112—C113 | 1.401 (9) | N10—C15 | 1.466 (8) |
C113—H1131 | 0.938 | C11—H111 | 0.975 |
C113—C114 | 1.373 (11) | C11—H112 | 0.960 |
C114—H1141 | 0.924 | C11—C12 | 1.483 (12) |
C114—C115 | 1.381 (11) | C12—H121 | 0.950 |
C115—H1151 | 0.926 | C12—H122 | 0.950 |
C115—C116 | 1.390 (9) | C12—C13 | 1.469 (8) |
C116—H1161 | 0.933 | C13—H131 | 0.950 |
C117—C118 | 1.386 (8) | C13—H132 | 0.950 |
C117—C122 | 1.386 (8) | C13—C14 | 1.508 (8) |
C118—H1181 | 0.926 | C14—H141 | 0.950 |
C118—C119 | 1.380 (9) | C14—H142 | 0.950 |
C119—H1191 | 0.930 | C14—H143 | 0.950 |
C119—C120 | 1.342 (10) | C15—H151 | 0.973 |
C120—H1201 | 0.933 | C15—H152 | 0.977 |
C120—C121 | 1.368 (11) | C15—C16 | 1.520 (12) |
C121—H1211 | 0.936 | C16—H161 | 0.969 |
C121—C122 | 1.408 (9) | C16—H162 | 0.958 |
C122—H1221 | 0.917 | C16—C17 | 1.520 (8) |
C123—C124 | 1.357 (8) | C17—H171 | 0.950 |
C123—C128 | 1.383 (8) | C17—H172 | 0.950 |
C124—H1241 | 0.930 | C17—C18 | 1.453 (9) |
C124—C125 | 1.403 (9) | C18—H181 | 0.950 |
C125—H1251 | 0.922 | C18—H182 | 0.950 |
C125—C126 | 1.356 (11) | C18—H183 | 0.950 |
C126—H1261 | 0.938 | N20—H201 | 0.892 |
C126—C127 | 1.368 (11) | N20—H202 | 0.897 |
C127—H1271 | 0.928 | N20—C21 | 1.504 (7) |
C127—C128 | 1.392 (9) | N20—C25 | 1.500 (7) |
C128—H1281 | 0.937 | C21—H211 | 0.964 |
O201—P202 | 1.510 (4) | C21—H212 | 0.968 |
P202—O203 | 1.549 (4) | C21—C22 | 1.513 (9) |
P202—O204 | 1.504 (4) | C22—H221 | 0.974 |
P202—C205 | 1.795 (7) | C22—H222 | 0.976 |
O203—H2031 | 0.850 | C22—C23 | 1.495 (7) |
C205—H2051 | 0.951 | C23—H231 | 0.975 |
C205—H2052 | 0.949 | C23—H232 | 0.969 |
C205—H2053 | 0.965 | C23—C24 | 1.521 (7) |
O206—P207 | 1.513 (4) | C24—H241 | 0.965 |
P207—O208 | 1.560 (4) | C24—H242 | 0.965 |
P207—O209 | 1.515 (4) | C24—H243 | 0.960 |
P207—C210 | 1.785 (7) | C25—H251 | 0.976 |
O208—H2081 | 0.850 | C25—H252 | 0.968 |
C210—H2101 | 0.956 | C25—C26 | 1.510 (9) |
C210—H2102 | 0.955 | C26—H261 | 0.973 |
C210—H2103 | 0.959 | C26—H262 | 0.976 |
C211—C212 | 1.393 (8) | C26—C27 | 1.520 (9) |
C211—C216 | 1.384 (9) | C27—H271 | 0.969 |
C212—H2121 | 0.939 | C27—H272 | 0.981 |
C212—C213 | 1.383 (9) | C27—C28 | 1.501 (10) |
C213—H2131 | 0.923 | C28—H281 | 0.960 |
C213—C214 | 1.352 (11) | C28—H282 | 0.967 |
C214—H2141 | 0.920 | C28—H283 | 0.961 |
O101—Sn1—O106 | 174.71 (14) | C215—C216—H2161 | 119.7 |
O101—Sn1—C111 | 89.15 (19) | C211—C216—H2161 | 118.5 |
O106—Sn1—C111 | 90.75 (18) | Sn2—C217—C218 | 121.3 (5) |
O101—Sn1—C117 | 88.80 (18) | Sn2—C217—C222 | 121.2 (4) |
O106—Sn1—C117 | 95.83 (18) | C218—C217—C222 | 117.5 (6) |
C111—Sn1—C117 | 119.9 (2) | C217—C218—H2181 | 119.0 |
O101—Sn1—C123 | 90.03 (17) | C217—C218—C219 | 121.3 (7) |
O106—Sn1—C123 | 85.50 (16) | H2181—C218—C219 | 119.7 |
C111—Sn1—C123 | 121.2 (2) | C218—C219—H2191 | 120.0 |
C117—Sn1—C123 | 118.8 (2) | C218—C219—C220 | 119.8 (7) |
Sn1—O101—P102 | 142.8 (2) | H2191—C219—C220 | 120.2 |
O101—P102—O103 | 110.3 (3) | C219—C220—H2201 | 118.5 |
O101—P102—O104 | 114.0 (2) | C219—C220—C221 | 121.3 (7) |
O103—P102—O104 | 108.4 (2) | H2201—C220—C221 | 120.2 |
O101—P102—C105 | 109.3 (3) | C220—C221—H2211 | 120.2 |
O103—P102—C105 | 103.6 (3) | C220—C221—C222 | 119.1 (8) |
O104—P102—C105 | 110.7 (3) | H2211—C221—C222 | 120.7 |
P102—O103—H1031 | 118.3 | C221—C222—C217 | 121.0 (6) |
P102—C105—H1051 | 110.6 | C221—C222—H2221 | 119.0 |
P102—C105—H1052 | 110.0 | C217—C222—H2221 | 120.1 |
H1051—C105—H1052 | 108.3 | Sn2—C223—C224 | 122.3 (4) |
P102—C105—H1053 | 110.7 | Sn2—C223—C228 | 119.9 (5) |
H1051—C105—H1053 | 109.0 | C224—C223—C228 | 117.8 (6) |
H1052—C105—H1053 | 108.3 | C223—C224—H2241 | 118.9 |
Sn1—O106—P107 | 143.2 (2) | C223—C224—C225 | 121.6 (6) |
O106—P107—O108 | 109.0 (2) | H2241—C224—C225 | 119.5 |
O106—P107—O109 | 114.1 (2) | C224—C225—H2251 | 119.8 |
O108—P107—O109 | 111.0 (2) | C224—C225—C226 | 120.8 (6) |
O106—P107—C110 | 108.1 (3) | H2251—C225—C226 | 119.4 |
O108—P107—C110 | 105.1 (3) | C225—C226—H2261 | 121.8 |
O109—P107—C110 | 109.1 (3) | C225—C226—C227 | 118.7 (6) |
P107—O108—H1081 | 122.5 | H2261—C226—C227 | 119.5 |
P107—C110—H1101 | 110.7 | C226—C227—H2271 | 119.9 |
P107—C110—H1102 | 110.6 | C226—C227—C228 | 121.6 (7) |
H1101—C110—H1102 | 109.1 | H2271—C227—C228 | 118.6 |
P107—C110—H1103 | 110.1 | C223—C228—C227 | 119.5 (7) |
H1101—C110—H1103 | 108.3 | C223—C228—H2281 | 119.7 |
H1102—C110—H1103 | 108.1 | C227—C228—H2281 | 120.7 |
Sn1—C111—C112 | 120.1 (5) | H101—N10—H102 | 108.9 |
Sn1—C111—C116 | 121.8 (4) | H101—N10—C11 | 108.9 |
C112—C111—C116 | 118.0 (5) | H102—N10—C11 | 109.5 |
C111—C112—H1121 | 120.9 | H101—N10—C15 | 107.9 |
C111—C112—C113 | 120.7 (6) | H102—N10—C15 | 109.9 |
H1121—C112—C113 | 118.4 | C11—N10—C15 | 111.8 (6) |
C112—C113—H1131 | 119.1 | N10—C11—H111 | 107.9 |
C112—C113—C114 | 120.8 (6) | N10—C11—H112 | 108.6 |
H1131—C113—C114 | 120.1 | H111—C11—H112 | 108.9 |
C113—C114—H1141 | 120.8 | N10—C11—C12 | 113.2 (6) |
C113—C114—C115 | 119.2 (7) | H111—C11—C12 | 106.7 |
H1141—C114—C115 | 120.0 | H112—C11—C12 | 111.3 |
C114—C115—H1151 | 119.5 | C11—C12—H121 | 106.4 |
C114—C115—C116 | 120.1 (7) | C11—C12—H122 | 105.5 |
H1151—C115—C116 | 120.4 | H121—C12—H122 | 109.5 |
C111—C116—C115 | 121.2 (6) | C11—C12—C13 | 119.9 (7) |
C111—C116—H1161 | 118.5 | H121—C12—C13 | 109.5 |
C115—C116—H1161 | 120.3 | H122—C12—C13 | 105.7 |
Sn1—C117—C118 | 122.1 (4) | C12—C13—H131 | 107.9 |
Sn1—C117—C122 | 121.1 (4) | C12—C13—H132 | 111.4 |
C118—C117—C122 | 116.7 (5) | H131—C13—H132 | 109.5 |
C117—C118—H1181 | 119.7 | C12—C13—C14 | 109.50 (2) |
C117—C118—C119 | 122.0 (6) | H131—C13—C14 | 108.1 |
H1181—C118—C119 | 118.3 | H132—C13—C14 | 110.4 |
C118—C119—H1191 | 119.8 | C13—C14—H141 | 110.3 |
C118—C119—C120 | 120.7 (6) | C13—C14—H142 | 109.0 |
H1191—C119—C120 | 119.5 | H141—C14—H142 | 109.5 |
C119—C120—H1201 | 120.6 | C13—C14—H143 | 109.1 |
C119—C120—C121 | 119.9 (6) | H141—C14—H143 | 109.5 |
H1201—C120—C121 | 119.5 | H142—C14—H143 | 109.5 |
C120—C121—H1211 | 119.5 | N10—C15—H151 | 107.3 |
C120—C121—C122 | 119.9 (7) | N10—C15—H152 | 109.6 |
H1211—C121—C122 | 120.6 | H151—C15—H152 | 109.9 |
C121—C122—C117 | 120.7 (6) | N10—C15—C16 | 110.9 (6) |
C121—C122—H1221 | 120.0 | H151—C15—C16 | 108.3 |
C117—C122—H1221 | 119.3 | H152—C15—C16 | 110.9 |
Sn1—C123—C124 | 120.8 (4) | C15—C16—H161 | 107.8 |
Sn1—C123—C128 | 121.1 (4) | C15—C16—H162 | 107.4 |
C124—C123—C128 | 118.0 (5) | H161—C16—H162 | 108.7 |
C123—C124—H1241 | 119.0 | C15—C16—C17 | 104.9 (7) |
C123—C124—C125 | 121.7 (6) | H161—C16—C17 | 112.7 |
H1241—C124—C125 | 119.3 | H162—C16—C17 | 114.9 |
C124—C125—H1251 | 120.8 | C16—C17—H171 | 109.2 |
C124—C125—C126 | 119.6 (7) | C16—C17—H172 | 109.7 |
H1251—C125—C126 | 119.6 | H171—C17—H172 | 109.5 |
C125—C126—H1261 | 119.8 | C16—C17—C18 | 109.50 (2) |
C125—C126—C127 | 119.7 (6) | H171—C17—C18 | 109.3 |
H1261—C126—C127 | 120.5 | H172—C17—C18 | 109.7 |
C126—C127—H1271 | 120.4 | C17—C18—H181 | 108.4 |
C126—C127—C128 | 120.4 (7) | C17—C18—H182 | 110.2 |
H1271—C127—C128 | 119.2 | H181—C18—H182 | 109.5 |
C127—C128—C123 | 120.5 (6) | C17—C18—H183 | 109.8 |
C127—C128—H1281 | 120.2 | H181—C18—H183 | 109.5 |
C123—C128—H1281 | 119.3 | H182—C18—H183 | 109.5 |
O201—Sn2—O206 | 174.15 (14) | H201—N20—H202 | 109.4 |
O201—Sn2—C211 | 90.47 (17) | H201—N20—C21 | 109.2 |
O206—Sn2—C211 | 89.08 (18) | H202—N20—C21 | 106.7 |
O201—Sn2—C217 | 85.41 (16) | H201—N20—C25 | 109.0 |
O206—Sn2—C217 | 89.91 (18) | H202—N20—C25 | 106.6 |
C211—Sn2—C217 | 122.4 (2) | C21—N20—C25 | 115.8 (5) |
O201—Sn2—C223 | 96.22 (19) | N20—C21—H211 | 108.4 |
O206—Sn2—C223 | 89.10 (19) | N20—C21—H212 | 109.2 |
C211—Sn2—C223 | 119.0 (2) | H211—C21—H212 | 108.5 |
C217—Sn2—C223 | 118.6 (2) | N20—C21—C22 | 111.4 (5) |
Sn2—O201—P202 | 140.8 (2) | H211—C21—C22 | 110.8 |
O201—P202—O203 | 107.4 (2) | H212—C21—C22 | 108.4 |
O201—P202—O204 | 114.2 (2) | C21—C22—H221 | 106.6 |
O203—P202—O204 | 111.8 (2) | C21—C22—H222 | 109.4 |
O201—P202—C205 | 108.9 (3) | H221—C22—H222 | 109.1 |
O203—P202—C205 | 105.6 (3) | C21—C22—C23 | 115.9 (5) |
O204—P202—C205 | 108.4 (3) | H221—C22—C23 | 107.7 |
P202—O203—H2031 | 122.9 | H222—C22—C23 | 107.9 |
P202—C205—H2051 | 110.5 | C22—C23—H231 | 109.5 |
P202—C205—H2052 | 110.7 | C22—C23—H232 | 109.1 |
H2051—C205—H2052 | 109.5 | H231—C23—H232 | 109.6 |
P202—C205—H2053 | 109.7 | C22—C23—C24 | 109.50 (2) |
H2051—C205—H2053 | 108.1 | H231—C23—C24 | 109.4 |
H2052—C205—H2053 | 108.3 | H232—C23—C24 | 109.6 |
Sn2—O206—P207 | 140.5 (2) | C23—C24—H241 | 108.3 |
O206—P207—O208 | 110.3 (3) | C23—C24—H242 | 111.1 |
O206—P207—O209 | 113.7 (2) | H241—C24—H242 | 109.2 |
O208—P207—O209 | 109.1 (2) | C23—C24—H243 | 110.6 |
O206—P207—C210 | 109.6 (3) | H241—C24—H243 | 109.2 |
O208—P207—C210 | 102.7 (3) | H242—C24—H243 | 108.4 |
O209—P207—C210 | 110.9 (3) | N20—C25—H251 | 107.4 |
P207—O208—H2081 | 119.1 | N20—C25—H252 | 108.2 |
P207—C210—H2101 | 110.7 | H251—C25—H252 | 108.6 |
P207—C210—H2102 | 110.7 | N20—C25—C26 | 111.0 (5) |
H2101—C210—H2102 | 108.5 | H251—C25—C26 | 110.3 |
P207—C210—H2103 | 110.3 | H252—C25—C26 | 111.2 |
H2101—C210—H2103 | 108.3 | C25—C26—H261 | 109.2 |
H2102—C210—H2103 | 108.3 | C25—C26—H262 | 108.7 |
Sn2—C211—C212 | 120.5 (4) | H261—C26—H262 | 108.7 |
Sn2—C211—C216 | 121.6 (5) | C25—C26—C27 | 112.8 (5) |
C212—C211—C216 | 117.9 (6) | H261—C26—C27 | 108.0 |
C211—C212—H2121 | 121.0 | H262—C26—C27 | 109.4 |
C211—C212—C213 | 120.2 (6) | C26—C27—H271 | 108.6 |
H2121—C212—C213 | 118.8 | C26—C27—H272 | 108.2 |
C212—C213—H2131 | 119.1 | H271—C27—H272 | 110.1 |
C212—C213—C214 | 121.7 (6) | C26—C27—C28 | 114.4 (6) |
H2131—C213—C214 | 119.2 | H271—C27—C28 | 107.1 |
C213—C214—H2141 | 120.6 | H272—C27—C28 | 108.4 |
C213—C214—C215 | 119.5 (6) | C27—C28—H281 | 109.6 |
H2141—C214—C215 | 119.9 | C27—C28—H282 | 112.2 |
C214—C215—H2151 | 119.8 | H281—C28—H282 | 108.6 |
C214—C215—C216 | 118.8 (7) | C27—C28—H283 | 108.0 |
H2151—C215—C216 | 121.4 | H281—C28—H283 | 109.1 |
C215—C216—C211 | 121.8 (7) | H282—C28—H283 | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O103—H1031···O109i | 0.85 | 1.73 | 2.582 (10) | 180 (1) |
O108—H1081···O104ii | 0.85 | 1.64 | 2.490 (10) | 180 (1) |
C122—H1221···O101 | 0.92 | 2.36 | 2.976 (10) | 124 (1) |
O203—H2031···O209iii | 0.85 | 1.63 | 2.478 (10) | 180 (1) |
O208—H2081···O204iv | 0.85 | 1.71 | 2.561 (10) | 180 (1) |
C228—H2281···O206 | 0.92 | 2.35 | 2.961 (10) | 124 (1) |
N10—H101···O209iii | 0.89 | 1.90 | 2.772 (10) | 165 (1) |
N10—H102···O109 | 0.90 | 1.92 | 2.777 (10) | 160 (1) |
C15—H152···O203 | 0.98 | 2.45 | 3.134 (10) | 127 (1) |
C16—H161···O103ii | 0.97 | 2.51 | 3.418 (10) | 156 (1) |
N20—H201···O204iv | 0.89 | 1.95 | 2.780 (10) | 154 (1) |
N20—H202···O104 | 0.90 | 1.88 | 2.756 (10) | 167 (1) |
C25—H252···O108i | 0.97 | 2.51 | 3.212 (10) | 129 (1) |
C26—H262···O208 | 0.98 | 2.52 | 3.302 (10) | 138 (1) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | (C8H20N)[Sn(C6H5)3(CH4O3P)2] |
Mr | 670.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 175 |
a, b, c (Å) | 16.1963 (8), 18.9088 (8), 21.1989 (11) |
β (°) | 93.220 (4) |
V (Å3) | 6482.0 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.93 |
Crystal size (mm) | 0.30 × 0.25 × 0.10 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2010) |
Tmin, Tmax | 0.961, 1.000 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 64843, 26060, 17225 |
Rint | 0.085 |
(sin θ/λ)max (Å−1) | 0.685 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.067, 0.99 |
No. of reflections | 17225 |
No. of parameters | 686 |
No. of restraints | 9 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.28, −1.66 |
Computer programs: CrysAlis PRO (Agilent, 2010), CrysAlis PRO (Agilent, 2010), Superflip (Palatinus & Chapuis, 2007), OLEX2 (Dolomanov et al., 2009), CRYSTALS (Betteridge et al., 2003) and publCIF (Westrip, 2010).
Sn1—O101 | 2.175 (4) | Sn2—O201 | 2.188 (3) |
Sn1—O106 | 2.188 (3) | Sn2—O206 | 2.169 (4) |
Sn1—C111 | 2.128 (6) | Sn2—C211 | 2.125 (6) |
Sn1—C117 | 2.137 (6) | Sn2—C217 | 2.126 (6) |
Sn1—C123 | 2.125 (5) | Sn2—C223 | 2.134 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O103—H1031···O109i | 0.850 | 1.732 | 2.582 (10) | 179.6 (2) |
O108—H1081···O104ii | 0.850 | 1.640 | 2.490 (10) | 179.9 (2) |
O203—H2031···O209iii | 0.850 | 1.628 | 2.478 (10) | 179.7 (3) |
O208—H2081···O204iv | 0.850 | 1.711 | 2.561 (10) | 179.70 (19) |
N10—H101···O209iii | 0.893 | 1.901 | 2.772 (10) | 164.57 (18) |
N10—H102···O109 | 0.896 | 1.920 | 2.777 (10) | 159.46 (19) |
N20—H201···O204iv | 0.892 | 1.951 | 2.780 (10) | 153.79 (17) |
N20—H202···O104 | 0.897 | 1.875 | 2.756 (10) | 167.17 (18) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+2, y+1/2, −z+1/2. |
References
Adair, B. A., Neeraj, S. & Cheetham, A. K. (2003). Chem. Mater. 15, 1518–1529. Web of Science CSD CrossRef CAS Google Scholar
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Chunlin, M., Mingqing, Y., Rufen, Z. & Lingyun, D. (2008). Inorg. Chim. Acta, 361, 2979–2984. Google Scholar
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100–1107. Web of Science CrossRef CAS IUCr Journals Google Scholar
Davies, A. G., Gielen, M., Pannell, K. H. & Tiekink, E. R. T. (2008). Tin Chemistry. Chichester: Wiley. Google Scholar
Diop, C. A. K., Bassene, S., Sidibe, M., Sarr-Diasse, A., Diop, L., Molloy, K. C., Mahon, M. F. & Toscano, R. A. (2002). Main Group Met. Chem. 25, 683–689. CrossRef CAS Google Scholar
Diop, T., Diop, L., Kociok-Köhn, G., Molloy, K. C. & Stoeckli-Evans, H. (2011). Acta Cryst. E67, m1674–m1675. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gielen, M. (2002). Appl. Organomet. Chem. 16, 481–494. Web of Science CrossRef CAS Google Scholar
Gueye, N., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2011). Main Group Met. Chem. 34, 3–4. Web of Science CrossRef CAS Google Scholar
Molloy, K. C., Purcell, T. G., Quill, K. & Nowell, I. W. (1984). J. Organomet. Chem. 267, 237–247. CSD CrossRef CAS Web of Science Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Prince, E. (1982). Mathematical Techniques in Crystallography and Materials. New York: Science Springer-Verlag. Google Scholar
Sow, Y., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2012). Main Group Met. Chem. 34, 127–130. Web of Science CrossRef Google Scholar
Watkin, D. (1994). Acta Cryst. A50, 411–437. CrossRef CAS Web of Science IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Organotin(IV) complexes are extensively studied due to their industrial applications as well as for their biocidal properties (Molloy et al., 1984; Gielen, 2002; Davies et al., 2008). Our group has conducted research on SnMe3 and SnPh3 residues containing derivatives with mono- and polybasic oxyanions such as C2O42- (Gueye et al., 2011; Sow et al., 2012) and PhP(H)O2- (Diop et al., 2011). Here we report the structure of the title compound, [(C4H9)2NH2]+[Sn(C6H5)3(CH3PO2OH)2]-, (I).
The asymmetric unit of compound (I) is illustrated in Fig. 1. It consists of two dibutylammonium cations and two organotin complexes consisting of two monodentate MePO3H- anions bonded to SnPh3; the SnIV atoms exhibit a trans trigonal bipyramidal coordination environment consisting of three phenyl carbon atoms and two MePO3H- oxygen atoms. The trigonal plane of the Sn atoms is defined by the three phenyl groups whereas the axial positions are occupied by oxygen atoms from the methyl hydrogenphosphate tetrahedra. A similar arrangement around tin(IV) has been observed in the crystal structure of {[(CH3)3Sn]4(O3PPh)2}n (Chunlin et al., 2008). The sums of the angles at the tin(IV) positions by the ipso-carbons atoms [119.9 (2)°, 121.2 (2)°, 118.8 (2)°, and 122.4 (2)°, 119.0 (2)° and 118.6 (2)° for the two SnIV entities] are 359.9° and 360.0°, respectively; the corresponding axial O101—Sn1—O106 and O201—Sn2—O206 angles are 174.71 (14)° and 174.15 (14)°, respectively, indicating a nearly perfect trans trigonal bipyramidal arrangement. The Sn—C bond lengths are almost identical within the experimental error (Sn1—C111: 2.128 (6) Å; Sn1—C117: 2.137 (6) Å; Sn1—C123 2.125 (5) Å; Sn2—C211: 2.125 (6) Å; Sn2—C217: 2.126 (6) Å; Sn2—C223 2.134 (6) Å] and lie in the range reported for related structures (Gueye et al., 2011). The two axial Sn—O distances, [Sn1—O101 2.175 (4) Å; Sn1—O106 2.188 (3) Å; Sn2—O201 2.188 (3) Å; Sn2—O206 2.169 (4) Å] are in the range of axial Sn—O distances (2.165 (4) and 2.434 (4) Å) observed in catena-trimethyltin(IV) methylphosphonate, [MePO3HSnMe3] (Diop et al., 2002), but are longer than the axial Sn—O distances [2.116 (2) Å and 2.132 (3) Å] observed in catena-(µ2-phenylphosphinato O, O')-chlorido-tin(II) (Adair et al., 2003). The geometry at the P sites is a distorted tetrahedron with bond angles ranging from 102.7 (3)° for O208—P207—C210 to 114.2 (2) for O201—P202—O204.
The stannate(IV) anions [(MePO3H)2SnPh3]- are linked by pairs of short O—H···O hydrogen bonds, involving the hydroxy group of the methyl hydrogenphosphate unit, and thus forming an infinite chain (Table 1, Fig. 2) along the b-direction. In the crystal, neighbouring chains are linked by N—H···O hydrogen bonds via the Bu2NH2+ cations, forming a supramolecular structure parallel to the ab plane.