metal-organic compounds
Tribenzylbis(triphenylarsine oxide-κO)tin(IV) tetraphenylborate
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The 7H7)3(C18H15AsO)2][B(C6H5)4], consists of discrete cations and anions; the tin atom of the cation is five-coordinated in a distorted trans-C3SnO2 trigonal-bipyramidal geometry [summation of C–Sn–C angles 360.0 (3)° and O–Sn–O angle 173.1 (1)°]. The structure contains voids of 113 (19) Å3, but no solvent molecule could reasonably be located there.
of the title salt, [Sn(CRelated literature
For the structure of a related triorganotin tetraphenylborate, see: Ng et al. (1989).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536810039450/xu5034sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039450/xu5034Isup2.hkl
Tribenzyltin chloride (0.21 g, 0.5 mmol), triphenylarsine oxide (0.32 g, 1 mmol) and sodium tetraphenylborate (0.17 g, 0.5 mmol) were dissolved in ethanol (100 ml). The solution was heated for an hour. Then the mixture was filtered and the filtrate evaporated at room temperature to obtain the colorless crystals.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2U(C). All aromatic rings were refined as rigid hexagons of 1.39 Å sides.The final difference Fourier map had a high peak at 3.22 Å from H39 and hole at 0.83 Å from Sn1. The peak could not be refined as a water O atom, and is probably an artifical of
The structure contains a voids of 113 (19) Å3, but no solvent molecule(s) could be located there reasonably.A suggestion for improving the aqueous solubility of triorganotin(IV) compounds, R3SnX, involves exchanging the X residue by the non-nucleophilic tetraphenylborate anion to generate a salt. However, to prevent aggregation into an oligopolymer, the triorganotin species itself must be stabilized by coordination by two neutral ligands. Of the number of such compounds synthesized, the
of only one, namely, [(p-ClC6H4)Ph2Sn(Ph3AsO)2][BPh4], has been reported (Ng et al., 1989). The compound exists as non-interacting cations and anions; the tin atom of the cation is five-coordinate in a trans-C3SnO2 trigonal bipyramidal geometry. The title tribenzyltin adduct (Scheme I, Figs. 1 & 2) is a similar non-interacting salt. The trans angle at tin is nearly linear, and the Sn–O–As skeleton is also nearly linear (Table 1).For the structure of a related triorganotin tetraphenylborate, see: Ng et al. (1989).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).[Sn(C7H7)3(C18H15AsO)](C24H20B) | Z = 2 |
Mr = 1355.72 | F(000) = 1388 |
Triclinic, P1 | Dx = 1.337 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 14.3288 (7) Å | Cell parameters from 4476 reflections |
b = 14.9477 (7) Å | θ = 2.3–28.2° |
c = 19.0994 (9) Å | µ = 1.40 mm−1 |
α = 69.220 (1)° | T = 100 K |
β = 73.972 (1)° | Cube, colorless |
γ = 62.683 (1)° | 0.1 × 0.1 × 0.1 mm |
V = 3366.4 (3) Å3 |
Bruker SMART APEX diffractometer | 17932 independent reflections |
Radiation source: fine-focus sealed tube | 12383 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
ω scans | θmax = 27.5°, θmin = 1.2° |
Absorption correction: multi-scan (TWINABS; Bruker, 2009) | h = −17→18 |
Tmin = 0.788, Tmax = 1.000 | k = −17→19 |
76329 measured reflections | l = 0→24 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.1059P)2] where P = (Fo2 + 2Fc2)/3 |
17932 reflections | (Δ/σ)max = 0.001 |
629 parameters | Δρmax = 2.06 e Å−3 |
0 restraints | Δρmin = −1.10 e Å−3 |
[Sn(C7H7)3(C18H15AsO)](C24H20B) | γ = 62.683 (1)° |
Mr = 1355.72 | V = 3366.4 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 14.3288 (7) Å | Mo Kα radiation |
b = 14.9477 (7) Å | µ = 1.40 mm−1 |
c = 19.0994 (9) Å | T = 100 K |
α = 69.220 (1)° | 0.1 × 0.1 × 0.1 mm |
β = 73.972 (1)° |
Bruker SMART APEX diffractometer | 17932 independent reflections |
Absorption correction: multi-scan (TWINABS; Bruker, 2009) | 12383 reflections with I > 2σ(I) |
Tmin = 0.788, Tmax = 1.000 | Rint = 0.068 |
76329 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 0.99 | Δρmax = 2.06 e Å−3 |
17932 reflections | Δρmin = −1.10 e Å−3 |
629 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.68359 (3) | 0.68691 (2) | 0.973010 (17) | 0.01457 (9) | |
As1 | 0.58668 (4) | 0.62392 (4) | 1.18383 (3) | 0.01939 (13) | |
As2 | 0.77629 (4) | 0.73481 (4) | 0.76041 (3) | 0.01624 (12) | |
O1 | 0.6109 (3) | 0.6565 (3) | 1.09025 (18) | 0.0275 (9) | |
O2 | 0.7611 (3) | 0.6987 (3) | 0.85374 (18) | 0.0239 (8) | |
B1 | 0.8611 (5) | 0.8755 (5) | 0.3893 (3) | 0.0213 (12) | |
C1 | 0.6220 (5) | 0.8523 (4) | 0.9593 (3) | 0.0271 (12) | |
H1A | 0.6472 | 0.8862 | 0.9075 | 0.033* | |
H1B | 0.5436 | 0.8813 | 0.9652 | 0.033* | |
C2 | 0.6556 (3) | 0.8774 (3) | 1.01589 (17) | 0.0260 (12) | |
C3 | 0.5848 (2) | 0.9025 (3) | 1.07932 (19) | 0.0261 (12) | |
H3 | 0.5151 | 0.9059 | 1.0860 | 0.031* | |
C4 | 0.6159 (2) | 0.9228 (3) | 1.13289 (16) | 0.0298 (13) | |
H4 | 0.5675 | 0.9399 | 1.1762 | 0.036* | |
C5 | 0.7177 (3) | 0.9179 (3) | 1.12305 (18) | 0.0300 (13) | |
H5 | 0.7390 | 0.9317 | 1.1597 | 0.036* | |
C6 | 0.7885 (2) | 0.8927 (3) | 1.0596 (2) | 0.0324 (13) | |
H6 | 0.8582 | 0.8894 | 1.0529 | 0.039* | |
C7 | 0.7574 (2) | 0.8725 (3) | 1.00605 (16) | 0.0283 (12) | |
H7 | 0.8058 | 0.8553 | 0.9627 | 0.034* | |
C8 | 0.8415 (4) | 0.6017 (4) | 1.0023 (3) | 0.0193 (10) | |
H8A | 0.8903 | 0.6274 | 0.9613 | 0.023* | |
H8B | 0.8434 | 0.6150 | 1.0489 | 0.023* | |
C9 | 0.8804 (3) | 0.48387 (18) | 1.01481 (17) | 0.0211 (11) | |
C10 | 0.8659 (3) | 0.4197 (2) | 1.08652 (14) | 0.0295 (13) | |
H10 | 0.8347 | 0.4484 | 1.1287 | 0.035* | |
C11 | 0.8970 (3) | 0.3137 (2) | 1.09650 (15) | 0.0364 (14) | |
H11 | 0.8871 | 0.2698 | 1.1455 | 0.044* | |
C12 | 0.9425 (3) | 0.27177 (18) | 1.0348 (2) | 0.0321 (13) | |
H12 | 0.9638 | 0.1993 | 1.0416 | 0.038* | |
C13 | 0.9570 (3) | 0.3359 (2) | 0.96306 (16) | 0.0270 (12) | |
H13 | 0.9882 | 0.3073 | 0.9209 | 0.032* | |
C14 | 0.9259 (3) | 0.4420 (2) | 0.95308 (13) | 0.0233 (11) | |
H14 | 0.9358 | 0.4858 | 0.9041 | 0.028* | |
C15 | 0.5900 (4) | 0.6224 (4) | 0.9532 (3) | 0.0204 (10) | |
H15A | 0.5939 | 0.6364 | 0.8980 | 0.024* | |
H15B | 0.6208 | 0.5457 | 0.9747 | 0.024* | |
C16 | 0.4742 (2) | 0.6659 (3) | 0.98714 (18) | 0.0210 (11) | |
C17 | 0.4353 (3) | 0.6003 (2) | 1.04697 (19) | 0.0319 (13) | |
H17 | 0.4809 | 0.5295 | 1.0660 | 0.038* | |
C18 | 0.3298 (3) | 0.6384 (3) | 1.07905 (18) | 0.0447 (17) | |
H18 | 0.3032 | 0.5935 | 1.1199 | 0.054* | |
C19 | 0.2631 (2) | 0.7420 (3) | 1.0513 (2) | 0.0452 (17) | |
H19 | 0.1910 | 0.7680 | 1.0732 | 0.054* | |
C20 | 0.3020 (2) | 0.8076 (2) | 0.9914 (2) | 0.0382 (15) | |
H20 | 0.2564 | 0.8784 | 0.9725 | 0.046* | |
C21 | 0.4075 (3) | 0.7696 (2) | 0.95937 (16) | 0.0302 (13) | |
H21 | 0.4341 | 0.8144 | 0.9185 | 0.036* | |
C22 | 0.4714 (2) | 0.7369 (3) | 1.21711 (19) | 0.0233 (11) | |
C23 | 0.4759 (3) | 0.7645 (3) | 1.2780 (2) | 0.0311 (13) | |
H23 | 0.5379 | 0.7284 | 1.3021 | 0.037* | |
C24 | 0.3896 (3) | 0.8448 (3) | 1.3037 (2) | 0.0439 (16) | |
H24 | 0.3926 | 0.8637 | 1.3453 | 0.053* | |
C25 | 0.2988 (3) | 0.8977 (3) | 1.2684 (2) | 0.054 (2) | |
H25 | 0.2398 | 0.9526 | 1.2860 | 0.065* | |
C26 | 0.2943 (3) | 0.8701 (3) | 1.2075 (2) | 0.0545 (19) | |
H26 | 0.2322 | 0.9062 | 1.1835 | 0.065* | |
C27 | 0.3806 (3) | 0.7897 (3) | 1.18188 (19) | 0.0414 (15) | |
H27 | 0.3775 | 0.7709 | 1.1403 | 0.050* | |
C28 | 0.7089 (2) | 0.5866 (3) | 1.22728 (17) | 0.0220 (11) | |
C29 | 0.7405 (3) | 0.4986 (2) | 1.28777 (18) | 0.0271 (12) | |
H29 | 0.7003 | 0.4571 | 1.3086 | 0.032* | |
C30 | 0.8308 (3) | 0.4715 (2) | 1.31782 (16) | 0.0334 (14) | |
H30 | 0.8523 | 0.4114 | 1.3592 | 0.040* | |
C31 | 0.8896 (2) | 0.5323 (3) | 1.28739 (19) | 0.0302 (13) | |
H31 | 0.9513 | 0.5138 | 1.3079 | 0.036* | |
C32 | 0.8581 (3) | 0.6202 (3) | 1.22690 (18) | 0.0297 (13) | |
H32 | 0.8983 | 0.6618 | 1.2061 | 0.036* | |
C33 | 0.7678 (3) | 0.6474 (2) | 1.19685 (15) | 0.0236 (11) | |
H33 | 0.7462 | 0.7075 | 1.1555 | 0.028* | |
C34 | 0.5484 (3) | 0.5070 (2) | 1.22101 (19) | 0.0230 (11) | |
C35 | 0.6048 (3) | 0.4222 (3) | 1.19022 (19) | 0.0374 (14) | |
H35 | 0.6599 | 0.4241 | 1.1491 | 0.045* | |
C36 | 0.5808 (3) | 0.3347 (2) | 1.2196 (2) | 0.0441 (16) | |
H36 | 0.6194 | 0.2767 | 1.1986 | 0.053* | |
C37 | 0.5003 (3) | 0.3319 (3) | 1.2798 (2) | 0.0420 (16) | |
H37 | 0.4838 | 0.2721 | 1.2999 | 0.050* | |
C38 | 0.4438 (3) | 0.4167 (3) | 1.31061 (19) | 0.0428 (16) | |
H38 | 0.3888 | 0.4148 | 1.3518 | 0.051* | |
C39 | 0.4678 (3) | 0.5043 (2) | 1.2812 (2) | 0.0345 (14) | |
H39 | 0.4292 | 0.5622 | 1.3023 | 0.041* | |
C40 | 0.8874 (2) | 0.7819 (3) | 0.72386 (17) | 0.0203 (10) | |
C41 | 0.9008 (3) | 0.8327 (3) | 0.76640 (15) | 0.0293 (12) | |
H41 | 0.8562 | 0.8410 | 0.8128 | 0.035* | |
C42 | 0.9793 (3) | 0.8713 (3) | 0.74100 (19) | 0.0344 (14) | |
H42 | 0.9884 | 0.9061 | 0.7701 | 0.041* | |
C43 | 1.0445 (2) | 0.8591 (3) | 0.67305 (19) | 0.0308 (13) | |
H43 | 1.0982 | 0.8856 | 0.6557 | 0.037* | |
C44 | 1.0311 (3) | 0.8083 (3) | 0.63051 (15) | 0.0321 (13) | |
H44 | 1.0757 | 0.8000 | 0.5841 | 0.038* | |
C45 | 0.9526 (3) | 0.7696 (3) | 0.65592 (16) | 0.0257 (12) | |
H45 | 0.9435 | 0.7349 | 0.6268 | 0.031* | |
C46 | 0.8060 (3) | 0.61942 (19) | 0.72419 (16) | 0.0176 (10) | |
C47 | 0.8266 (3) | 0.5212 (2) | 0.77497 (12) | 0.0217 (11) | |
H47 | 0.8239 | 0.5126 | 0.8271 | 0.026* | |
C48 | 0.8510 (3) | 0.43569 (18) | 0.74944 (15) | 0.0254 (11) | |
H48 | 0.8651 | 0.3686 | 0.7841 | 0.030* | |
C49 | 0.8549 (3) | 0.4483 (2) | 0.67314 (17) | 0.0246 (11) | |
H49 | 0.8716 | 0.3899 | 0.6557 | 0.030* | |
C50 | 0.8344 (3) | 0.5465 (2) | 0.62236 (12) | 0.0253 (12) | |
H50 | 0.8370 | 0.5551 | 0.5702 | 0.030* | |
C51 | 0.8099 (3) | 0.63205 (18) | 0.64788 (14) | 0.0230 (11) | |
H51 | 0.7958 | 0.6992 | 0.6132 | 0.028* | |
C52 | 0.6509 (2) | 0.8450 (2) | 0.72226 (17) | 0.0182 (10) | |
C53 | 0.5530 (2) | 0.8515 (2) | 0.76437 (14) | 0.0231 (11) | |
H53 | 0.5495 | 0.8038 | 0.8127 | 0.028* | |
C54 | 0.46027 (19) | 0.9277 (3) | 0.73580 (17) | 0.0263 (12) | |
H54 | 0.3934 | 0.9321 | 0.7646 | 0.032* | |
C55 | 0.4654 (2) | 0.9974 (2) | 0.66512 (18) | 0.0274 (12) | |
H55 | 0.4020 | 1.0495 | 0.6456 | 0.033* | |
C56 | 0.5633 (3) | 0.9910 (2) | 0.62301 (14) | 0.0281 (12) | |
H56 | 0.5668 | 1.0387 | 0.5747 | 0.034* | |
C57 | 0.6561 (2) | 0.9148 (3) | 0.65158 (16) | 0.0225 (11) | |
H57 | 0.7230 | 0.9104 | 0.6228 | 0.027* | |
C58 | 0.9777 (2) | 0.7831 (2) | 0.41918 (18) | 0.0221 (11) | |
C59 | 1.0692 (3) | 0.8022 (2) | 0.39184 (17) | 0.0251 (11) | |
H59 | 1.0669 | 0.8654 | 0.3549 | 0.030* | |
C60 | 1.1642 (2) | 0.7287 (3) | 0.41855 (19) | 0.0301 (13) | |
H60 | 1.2268 | 0.7417 | 0.3999 | 0.036* | |
C61 | 1.1677 (2) | 0.6362 (2) | 0.47260 (19) | 0.0319 (13) | |
H61 | 1.2326 | 0.5860 | 0.4909 | 0.038* | |
C62 | 1.0762 (3) | 0.6172 (2) | 0.49995 (16) | 0.0270 (12) | |
H62 | 1.0785 | 0.5540 | 0.5369 | 0.032* | |
C63 | 0.9812 (2) | 0.6906 (2) | 0.47324 (17) | 0.0227 (11) | |
H63 | 0.9186 | 0.6776 | 0.4919 | 0.027* | |
C64 | 0.7728 (2) | 0.8193 (2) | 0.41460 (17) | 0.0193 (10) | |
C65 | 0.6996 (3) | 0.8321 (2) | 0.47932 (16) | 0.0221 (11) | |
H65 | 0.6983 | 0.8731 | 0.5081 | 0.027* | |
C66 | 0.6283 (2) | 0.7847 (3) | 0.50194 (15) | 0.0284 (12) | |
H66 | 0.5783 | 0.7935 | 0.5462 | 0.034* | |
C67 | 0.6303 (3) | 0.7246 (3) | 0.45982 (19) | 0.0303 (13) | |
H67 | 0.5816 | 0.6923 | 0.4753 | 0.036* | |
C68 | 0.7035 (3) | 0.7119 (3) | 0.39510 (19) | 0.0312 (13) | |
H68 | 0.7048 | 0.6708 | 0.3663 | 0.037* | |
C69 | 0.7747 (2) | 0.7592 (3) | 0.37248 (16) | 0.0268 (12) | |
H69 | 0.8247 | 0.7505 | 0.3282 | 0.032* | |
C70 | 0.8132 (2) | 0.9726 (2) | 0.43254 (17) | 0.0189 (10) | |
C71 | 0.7171 (2) | 1.0564 (2) | 0.41706 (17) | 0.0223 (11) | |
H71 | 0.6772 | 1.0576 | 0.3842 | 0.027* | |
C72 | 0.6794 (2) | 1.1384 (2) | 0.44967 (19) | 0.0278 (12) | |
H72 | 0.6137 | 1.1957 | 0.4391 | 0.033* | |
C73 | 0.7378 (3) | 1.1367 (2) | 0.49776 (18) | 0.0294 (13) | |
H73 | 0.7120 | 1.1928 | 0.5200 | 0.035* | |
C74 | 0.8339 (3) | 1.0529 (3) | 0.51324 (17) | 0.0294 (13) | |
H74 | 0.8738 | 1.0517 | 0.5461 | 0.035* | |
C75 | 0.8716 (2) | 0.9708 (2) | 0.48063 (18) | 0.0233 (11) | |
H75 | 0.9373 | 0.9135 | 0.4912 | 0.028* | |
C76 | 0.8834 (3) | 0.9200 (2) | 0.29298 (12) | 0.0216 (11) | |
C77 | 0.9541 (3) | 0.84763 (19) | 0.25304 (17) | 0.0276 (12) | |
H77 | 0.9879 | 0.7763 | 0.2792 | 0.033* | |
C78 | 0.9755 (3) | 0.8796 (2) | 0.17476 (17) | 0.0329 (14) | |
H78 | 1.0238 | 0.8301 | 0.1475 | 0.040* | |
C79 | 0.9261 (3) | 0.9839 (3) | 0.13641 (12) | 0.0314 (13) | |
H79 | 0.9407 | 1.0058 | 0.0829 | 0.038* | |
C80 | 0.8553 (3) | 1.05630 (19) | 0.17636 (16) | 0.0267 (12) | |
H80 | 0.8216 | 1.1276 | 0.1502 | 0.032* | |
C81 | 0.8340 (2) | 1.0244 (2) | 0.25464 (16) | 0.0210 (11) | |
H81 | 0.7856 | 1.0738 | 0.2819 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01473 (17) | 0.01544 (17) | 0.01310 (16) | −0.00479 (13) | −0.00460 (12) | −0.00301 (13) |
As1 | 0.0186 (3) | 0.0259 (3) | 0.0140 (3) | −0.0083 (2) | −0.0023 (2) | −0.0063 (2) |
As2 | 0.0163 (3) | 0.0201 (3) | 0.0120 (2) | −0.0081 (2) | −0.00233 (19) | −0.0025 (2) |
O1 | 0.030 (2) | 0.041 (2) | 0.0141 (18) | −0.0184 (19) | −0.0009 (15) | −0.0061 (17) |
O2 | 0.025 (2) | 0.031 (2) | 0.0131 (17) | −0.0127 (17) | −0.0052 (15) | 0.0002 (15) |
B1 | 0.028 (3) | 0.021 (3) | 0.018 (3) | −0.010 (3) | −0.007 (2) | −0.005 (2) |
C1 | 0.030 (3) | 0.022 (3) | 0.028 (3) | −0.007 (2) | −0.009 (2) | −0.008 (2) |
C2 | 0.026 (3) | 0.016 (3) | 0.033 (3) | −0.006 (2) | −0.007 (2) | −0.006 (2) |
C3 | 0.021 (3) | 0.015 (3) | 0.037 (3) | −0.001 (2) | −0.011 (2) | −0.005 (2) |
C4 | 0.035 (3) | 0.024 (3) | 0.033 (3) | −0.012 (3) | −0.001 (3) | −0.013 (2) |
C5 | 0.037 (3) | 0.031 (3) | 0.034 (3) | −0.017 (3) | −0.009 (3) | −0.014 (3) |
C6 | 0.026 (3) | 0.033 (3) | 0.047 (4) | −0.011 (3) | −0.009 (3) | −0.019 (3) |
C7 | 0.026 (3) | 0.026 (3) | 0.033 (3) | −0.009 (2) | −0.001 (2) | −0.013 (2) |
C8 | 0.017 (3) | 0.025 (3) | 0.018 (2) | −0.011 (2) | −0.006 (2) | −0.002 (2) |
C9 | 0.018 (3) | 0.021 (3) | 0.019 (3) | −0.003 (2) | −0.008 (2) | −0.002 (2) |
C10 | 0.022 (3) | 0.031 (3) | 0.023 (3) | −0.003 (2) | −0.002 (2) | −0.003 (2) |
C11 | 0.034 (3) | 0.024 (3) | 0.036 (3) | −0.008 (3) | 0.000 (3) | 0.001 (3) |
C12 | 0.028 (3) | 0.022 (3) | 0.040 (3) | −0.010 (2) | −0.003 (3) | −0.003 (3) |
C13 | 0.023 (3) | 0.030 (3) | 0.032 (3) | −0.008 (2) | −0.005 (2) | −0.014 (2) |
C14 | 0.022 (3) | 0.023 (3) | 0.020 (3) | −0.005 (2) | −0.009 (2) | −0.002 (2) |
C15 | 0.020 (3) | 0.024 (3) | 0.020 (3) | −0.012 (2) | −0.002 (2) | −0.006 (2) |
C16 | 0.021 (3) | 0.030 (3) | 0.020 (3) | −0.015 (2) | −0.004 (2) | −0.008 (2) |
C17 | 0.039 (3) | 0.039 (3) | 0.026 (3) | −0.026 (3) | 0.007 (3) | −0.012 (3) |
C18 | 0.044 (4) | 0.055 (4) | 0.045 (4) | −0.038 (4) | 0.019 (3) | −0.019 (3) |
C19 | 0.020 (3) | 0.072 (5) | 0.059 (4) | −0.026 (3) | 0.009 (3) | −0.036 (4) |
C20 | 0.022 (3) | 0.047 (4) | 0.043 (4) | −0.007 (3) | −0.011 (3) | −0.012 (3) |
C21 | 0.031 (3) | 0.042 (3) | 0.021 (3) | −0.017 (3) | −0.004 (2) | −0.009 (3) |
C22 | 0.024 (3) | 0.024 (3) | 0.021 (3) | −0.012 (2) | 0.002 (2) | −0.006 (2) |
C23 | 0.035 (3) | 0.034 (3) | 0.029 (3) | −0.020 (3) | 0.003 (2) | −0.012 (3) |
C24 | 0.050 (4) | 0.039 (4) | 0.042 (4) | −0.015 (3) | 0.007 (3) | −0.023 (3) |
C25 | 0.055 (5) | 0.038 (4) | 0.053 (4) | −0.012 (4) | 0.013 (4) | −0.018 (3) |
C26 | 0.027 (4) | 0.049 (4) | 0.064 (5) | 0.000 (3) | −0.005 (3) | −0.011 (4) |
C27 | 0.037 (4) | 0.049 (4) | 0.035 (4) | −0.014 (3) | −0.005 (3) | −0.013 (3) |
C28 | 0.023 (3) | 0.025 (3) | 0.019 (3) | −0.009 (2) | −0.003 (2) | −0.007 (2) |
C29 | 0.033 (3) | 0.028 (3) | 0.025 (3) | −0.014 (3) | −0.006 (2) | −0.007 (2) |
C30 | 0.026 (3) | 0.038 (3) | 0.027 (3) | 0.000 (3) | −0.016 (2) | −0.007 (3) |
C31 | 0.017 (3) | 0.043 (3) | 0.029 (3) | −0.006 (3) | −0.006 (2) | −0.014 (3) |
C32 | 0.029 (3) | 0.046 (4) | 0.022 (3) | −0.021 (3) | −0.002 (2) | −0.011 (3) |
C33 | 0.031 (3) | 0.024 (3) | 0.016 (2) | −0.012 (2) | −0.002 (2) | −0.005 (2) |
C34 | 0.022 (3) | 0.027 (3) | 0.020 (3) | −0.008 (2) | −0.006 (2) | −0.005 (2) |
C35 | 0.037 (4) | 0.036 (3) | 0.037 (3) | −0.015 (3) | 0.003 (3) | −0.014 (3) |
C36 | 0.051 (4) | 0.030 (3) | 0.053 (4) | −0.014 (3) | −0.008 (3) | −0.015 (3) |
C37 | 0.051 (4) | 0.037 (4) | 0.045 (4) | −0.026 (3) | −0.009 (3) | −0.004 (3) |
C38 | 0.045 (4) | 0.045 (4) | 0.038 (4) | −0.026 (3) | 0.005 (3) | −0.009 (3) |
C39 | 0.034 (3) | 0.041 (4) | 0.034 (3) | −0.021 (3) | 0.006 (3) | −0.016 (3) |
C40 | 0.020 (3) | 0.023 (3) | 0.016 (2) | −0.009 (2) | −0.006 (2) | 0.000 (2) |
C41 | 0.032 (3) | 0.034 (3) | 0.024 (3) | −0.016 (3) | 0.001 (2) | −0.009 (2) |
C42 | 0.037 (4) | 0.039 (3) | 0.038 (3) | −0.024 (3) | −0.013 (3) | −0.004 (3) |
C43 | 0.029 (3) | 0.030 (3) | 0.031 (3) | −0.019 (3) | −0.015 (3) | 0.011 (2) |
C44 | 0.033 (3) | 0.037 (3) | 0.024 (3) | −0.022 (3) | −0.002 (2) | 0.004 (2) |
C45 | 0.024 (3) | 0.034 (3) | 0.021 (3) | −0.016 (2) | −0.002 (2) | −0.004 (2) |
C46 | 0.020 (3) | 0.012 (2) | 0.021 (2) | −0.004 (2) | −0.011 (2) | −0.0016 (19) |
C47 | 0.021 (3) | 0.027 (3) | 0.016 (2) | −0.010 (2) | −0.005 (2) | −0.002 (2) |
C48 | 0.027 (3) | 0.021 (3) | 0.027 (3) | −0.012 (2) | −0.004 (2) | −0.002 (2) |
C49 | 0.026 (3) | 0.024 (3) | 0.025 (3) | −0.011 (2) | −0.001 (2) | −0.009 (2) |
C50 | 0.031 (3) | 0.028 (3) | 0.019 (3) | −0.013 (2) | −0.003 (2) | −0.006 (2) |
C51 | 0.029 (3) | 0.024 (3) | 0.013 (2) | −0.012 (2) | 0.000 (2) | −0.003 (2) |
C52 | 0.020 (3) | 0.016 (2) | 0.020 (2) | −0.004 (2) | −0.009 (2) | −0.006 (2) |
C53 | 0.023 (3) | 0.022 (3) | 0.018 (3) | −0.005 (2) | −0.006 (2) | −0.002 (2) |
C54 | 0.015 (3) | 0.034 (3) | 0.028 (3) | −0.007 (2) | −0.002 (2) | −0.012 (2) |
C55 | 0.035 (3) | 0.017 (3) | 0.031 (3) | −0.002 (2) | −0.022 (3) | −0.006 (2) |
C56 | 0.033 (3) | 0.026 (3) | 0.021 (3) | −0.013 (3) | −0.006 (2) | 0.002 (2) |
C57 | 0.020 (3) | 0.023 (3) | 0.018 (3) | −0.008 (2) | −0.003 (2) | −0.001 (2) |
C58 | 0.029 (3) | 0.022 (3) | 0.016 (2) | −0.008 (2) | −0.003 (2) | −0.008 (2) |
C59 | 0.019 (3) | 0.028 (3) | 0.031 (3) | −0.011 (2) | −0.004 (2) | −0.010 (2) |
C60 | 0.024 (3) | 0.038 (3) | 0.037 (3) | −0.013 (3) | −0.011 (2) | −0.014 (3) |
C61 | 0.030 (3) | 0.035 (3) | 0.028 (3) | −0.002 (3) | −0.016 (3) | −0.010 (3) |
C62 | 0.037 (3) | 0.030 (3) | 0.012 (2) | −0.011 (3) | −0.008 (2) | −0.002 (2) |
C63 | 0.022 (3) | 0.028 (3) | 0.018 (3) | −0.009 (2) | −0.003 (2) | −0.007 (2) |
C64 | 0.014 (2) | 0.019 (2) | 0.022 (3) | −0.002 (2) | −0.010 (2) | −0.003 (2) |
C65 | 0.027 (3) | 0.023 (3) | 0.015 (2) | −0.011 (2) | −0.008 (2) | 0.002 (2) |
C66 | 0.036 (3) | 0.034 (3) | 0.019 (3) | −0.020 (3) | −0.006 (2) | 0.000 (2) |
C67 | 0.026 (3) | 0.028 (3) | 0.040 (3) | −0.017 (3) | −0.009 (3) | −0.002 (3) |
C68 | 0.032 (3) | 0.034 (3) | 0.038 (3) | −0.015 (3) | −0.005 (3) | −0.019 (3) |
C69 | 0.018 (3) | 0.029 (3) | 0.037 (3) | −0.009 (2) | −0.002 (2) | −0.015 (3) |
C70 | 0.023 (3) | 0.023 (3) | 0.017 (2) | −0.017 (2) | −0.003 (2) | −0.002 (2) |
C71 | 0.022 (3) | 0.030 (3) | 0.023 (3) | −0.016 (2) | 0.000 (2) | −0.011 (2) |
C72 | 0.028 (3) | 0.026 (3) | 0.027 (3) | −0.009 (2) | −0.001 (2) | −0.009 (2) |
C73 | 0.035 (3) | 0.038 (3) | 0.027 (3) | −0.025 (3) | 0.013 (2) | −0.020 (3) |
C74 | 0.039 (3) | 0.035 (3) | 0.023 (3) | −0.024 (3) | 0.001 (2) | −0.008 (2) |
C75 | 0.022 (3) | 0.032 (3) | 0.022 (3) | −0.018 (2) | −0.003 (2) | −0.006 (2) |
C76 | 0.015 (3) | 0.026 (3) | 0.021 (3) | −0.003 (2) | −0.004 (2) | −0.010 (2) |
C77 | 0.028 (3) | 0.025 (3) | 0.022 (3) | −0.005 (2) | −0.005 (2) | −0.005 (2) |
C78 | 0.031 (3) | 0.045 (4) | 0.020 (3) | −0.010 (3) | −0.001 (2) | −0.014 (3) |
C79 | 0.031 (3) | 0.051 (4) | 0.014 (3) | −0.023 (3) | −0.002 (2) | −0.003 (3) |
C80 | 0.037 (3) | 0.028 (3) | 0.023 (3) | −0.019 (3) | −0.010 (2) | −0.002 (2) |
C81 | 0.025 (3) | 0.019 (3) | 0.021 (3) | −0.008 (2) | −0.007 (2) | −0.005 (2) |
Sn1—C1 | 2.150 (5) | C36—C37 | 1.3900 |
Sn1—C8 | 2.145 (5) | C36—H36 | 0.9500 |
Sn1—C15 | 2.144 (5) | C37—C38 | 1.3900 |
Sn1—O1 | 2.175 (3) | C37—H37 | 0.9500 |
Sn1—O2 | 2.225 (3) | C38—C39 | 1.3900 |
As1—O1 | 1.657 (3) | C38—H38 | 0.9500 |
As1—C22 | 1.899 (3) | C39—H39 | 0.9500 |
As1—C34 | 1.909 (3) | C40—C41 | 1.3900 |
As1—C28 | 1.909 (2) | C40—C45 | 1.3900 |
As2—O2 | 1.651 (3) | C41—C42 | 1.3900 |
As2—C40 | 1.893 (2) | C41—H41 | 0.9500 |
As2—C52 | 1.904 (2) | C42—C43 | 1.3900 |
As2—C46 | 1.909 (2) | C42—H42 | 0.9500 |
B1—C58 | 1.695 (6) | C43—C44 | 1.3900 |
B1—C70 | 1.697 (6) | C43—H43 | 0.9500 |
B1—C64 | 1.701 (6) | C44—C45 | 1.3900 |
B1—C76 | 1.712 (6) | C44—H44 | 0.9500 |
C1—C2 | 1.511 (5) | C45—H45 | 0.9500 |
C1—H1A | 0.9900 | C46—C47 | 1.3900 |
C1—H1B | 0.9900 | C46—C51 | 1.3900 |
C2—C3 | 1.3900 | C47—C48 | 1.3900 |
C2—C7 | 1.3900 | C47—H47 | 0.9500 |
C3—C4 | 1.3900 | C48—C49 | 1.3900 |
C3—H3 | 0.9500 | C48—H48 | 0.9500 |
C4—C5 | 1.3900 | C49—C50 | 1.3900 |
C4—H4 | 0.9500 | C49—H49 | 0.9500 |
C5—C6 | 1.3900 | C50—C51 | 1.3900 |
C5—H5 | 0.9500 | C50—H50 | 0.9500 |
C6—C7 | 1.3900 | C51—H51 | 0.9500 |
C6—H6 | 0.9500 | C52—C53 | 1.3900 |
C7—H7 | 0.9500 | C52—C57 | 1.3900 |
C8—C9 | 1.531 (5) | C53—C54 | 1.3900 |
C8—H8A | 0.9900 | C53—H53 | 0.9500 |
C8—H8B | 0.9900 | C54—C55 | 1.3900 |
C9—C10 | 1.3900 | C54—H54 | 0.9500 |
C9—C14 | 1.3900 | C55—C56 | 1.3900 |
C10—C11 | 1.3900 | C55—H55 | 0.9500 |
C10—H10 | 0.9500 | C56—C57 | 1.3900 |
C11—C12 | 1.3900 | C56—H56 | 0.9500 |
C11—H11 | 0.9500 | C57—H57 | 0.9500 |
C12—C13 | 1.3900 | C58—C59 | 1.3900 |
C12—H12 | 0.9500 | C58—C63 | 1.3900 |
C13—C14 | 1.3900 | C59—C60 | 1.3900 |
C13—H13 | 0.9500 | C59—H59 | 0.9500 |
C14—H14 | 0.9500 | C60—C61 | 1.3900 |
C15—C16 | 1.520 (5) | C60—H60 | 0.9500 |
C15—H15A | 0.9900 | C61—C62 | 1.3900 |
C15—H15B | 0.9900 | C61—H61 | 0.9500 |
C16—C17 | 1.3900 | C62—C63 | 1.3900 |
C16—C21 | 1.3900 | C62—H62 | 0.9500 |
C17—C18 | 1.3900 | C63—H63 | 0.9500 |
C17—H17 | 0.9500 | C64—C65 | 1.3900 |
C18—C19 | 1.3900 | C64—C69 | 1.3900 |
C18—H18 | 0.9500 | C65—C66 | 1.3900 |
C19—C20 | 1.3900 | C65—H65 | 0.9500 |
C19—H19 | 0.9500 | C66—C67 | 1.3900 |
C20—C21 | 1.3900 | C66—H66 | 0.9500 |
C20—H20 | 0.9500 | C67—C68 | 1.3900 |
C21—H21 | 0.9500 | C67—H67 | 0.9500 |
C22—C23 | 1.3900 | C68—C69 | 1.3900 |
C22—C27 | 1.3900 | C68—H68 | 0.9500 |
C23—C24 | 1.3900 | C69—H69 | 0.9500 |
C23—H23 | 0.9500 | C70—C71 | 1.3900 |
C24—C25 | 1.3900 | C70—C75 | 1.3900 |
C24—H24 | 0.9500 | C71—C72 | 1.3900 |
C25—C26 | 1.3900 | C71—H71 | 0.9500 |
C25—H25 | 0.9500 | C72—C73 | 1.3900 |
C26—C27 | 1.3900 | C72—H72 | 0.9500 |
C26—H26 | 0.9500 | C73—C74 | 1.3900 |
C27—H27 | 0.9500 | C73—H73 | 0.9500 |
C28—C29 | 1.3900 | C74—C75 | 1.3900 |
C28—C33 | 1.3900 | C74—H74 | 0.9500 |
C29—C30 | 1.3900 | C75—H75 | 0.9500 |
C29—H29 | 0.9500 | C76—C77 | 1.3900 |
C30—C31 | 1.3900 | C76—C81 | 1.3900 |
C30—H30 | 0.9500 | C77—C78 | 1.3900 |
C31—C32 | 1.3900 | C77—H77 | 0.9500 |
C31—H31 | 0.9500 | C78—C79 | 1.3900 |
C32—C33 | 1.3900 | C78—H78 | 0.9500 |
C32—H32 | 0.9500 | C79—C80 | 1.3900 |
C33—H33 | 0.9500 | C79—H79 | 0.9500 |
C34—C35 | 1.3900 | C80—C81 | 1.3900 |
C34—C39 | 1.3900 | C80—H80 | 0.9500 |
C35—C36 | 1.3900 | C81—H81 | 0.9500 |
C35—H35 | 0.9500 | ||
C1—Sn1—C8 | 114.4 (2) | C34—C35—C36 | 120.0 |
C1—Sn1—C15 | 119.7 (2) | C34—C35—H35 | 120.0 |
C8—Sn1—C15 | 125.9 (2) | C36—C35—H35 | 120.0 |
C15—Sn1—O1 | 86.24 (16) | C35—C36—C37 | 120.0 |
C8—Sn1—O1 | 93.12 (16) | C35—C36—H36 | 120.0 |
C1—Sn1—O1 | 93.11 (18) | C37—C36—H36 | 120.0 |
C15—Sn1—O2 | 88.98 (16) | C38—C37—C36 | 120.0 |
C8—Sn1—O2 | 85.65 (16) | C38—C37—H37 | 120.0 |
C1—Sn1—O2 | 93.57 (17) | C36—C37—H37 | 120.0 |
O1—Sn1—O2 | 173.1 (1) | C37—C38—C39 | 120.0 |
O1—As1—C22 | 109.92 (17) | C37—C38—H38 | 120.0 |
O1—As1—C34 | 111.14 (16) | C39—C38—H38 | 120.0 |
C22—As1—C34 | 107.37 (16) | C38—C39—C34 | 120.0 |
O1—As1—C28 | 110.98 (16) | C38—C39—H39 | 120.0 |
C22—As1—C28 | 109.80 (15) | C34—C39—H39 | 120.0 |
C34—As1—C28 | 107.54 (15) | C41—C40—C45 | 120.0 |
O2—As2—C40 | 109.27 (16) | C41—C40—As2 | 117.73 (17) |
O2—As2—C52 | 111.94 (16) | C45—C40—As2 | 122.25 (17) |
C40—As2—C52 | 108.31 (14) | C40—C41—C42 | 120.0 |
O2—As2—C46 | 109.16 (15) | C40—C41—H41 | 120.0 |
C40—As2—C46 | 111.20 (14) | C42—C41—H41 | 120.0 |
C52—As2—C46 | 106.96 (14) | C43—C42—C41 | 120.0 |
As1—O1—Sn1 | 165.3 (2) | C43—C42—H42 | 120.0 |
As2—O2—Sn1 | 160.3 (2) | C41—C42—H42 | 120.0 |
C58—B1—C70 | 109.7 (3) | C44—C43—C42 | 120.0 |
C58—B1—C64 | 108.3 (4) | C44—C43—H43 | 120.0 |
C70—B1—C64 | 108.3 (4) | C42—C43—H43 | 120.0 |
C58—B1—C76 | 107.9 (4) | C43—C44—C45 | 120.0 |
C70—B1—C76 | 112.3 (4) | C43—C44—H44 | 120.0 |
C64—B1—C76 | 110.3 (3) | C45—C44—H44 | 120.0 |
C2—C1—Sn1 | 112.2 (3) | C44—C45—C40 | 120.0 |
C2—C1—H1A | 109.2 | C44—C45—H45 | 120.0 |
Sn1—C1—H1A | 109.2 | C40—C45—H45 | 120.0 |
C2—C1—H1B | 109.2 | C47—C46—C51 | 120.0 |
Sn1—C1—H1B | 109.2 | C47—C46—As2 | 119.09 (16) |
H1A—C1—H1B | 107.9 | C51—C46—As2 | 120.89 (16) |
C3—C2—C7 | 120.0 | C46—C47—C48 | 120.0 |
C3—C2—C1 | 119.5 (3) | C46—C47—H47 | 120.0 |
C7—C2—C1 | 120.5 (3) | C48—C47—H47 | 120.0 |
C4—C3—C2 | 120.0 | C49—C48—C47 | 120.0 |
C4—C3—H3 | 120.0 | C49—C48—H48 | 120.0 |
C2—C3—H3 | 120.0 | C47—C48—H48 | 120.0 |
C3—C4—C5 | 120.0 | C50—C49—C48 | 120.0 |
C3—C4—H4 | 120.0 | C50—C49—H49 | 120.0 |
C5—C4—H4 | 120.0 | C48—C49—H49 | 120.0 |
C4—C5—C6 | 120.0 | C49—C50—C51 | 120.0 |
C4—C5—H5 | 120.0 | C49—C50—H50 | 120.0 |
C6—C5—H5 | 120.0 | C51—C50—H50 | 120.0 |
C7—C6—C5 | 120.0 | C50—C51—C46 | 120.0 |
C7—C6—H6 | 120.0 | C50—C51—H51 | 120.0 |
C5—C6—H6 | 120.0 | C46—C51—H51 | 120.0 |
C6—C7—C2 | 120.0 | C53—C52—C57 | 120.0 |
C6—C7—H7 | 120.0 | C53—C52—As2 | 118.93 (17) |
C2—C7—H7 | 120.0 | C57—C52—As2 | 120.97 (17) |
C9—C8—Sn1 | 112.6 (3) | C52—C53—C54 | 120.0 |
C9—C8—H8A | 109.1 | C52—C53—H53 | 120.0 |
Sn1—C8—H8A | 109.1 | C54—C53—H53 | 120.0 |
C9—C8—H8B | 109.1 | C53—C54—C55 | 120.0 |
Sn1—C8—H8B | 109.1 | C53—C54—H54 | 120.0 |
H8A—C8—H8B | 107.8 | C55—C54—H54 | 120.0 |
C10—C9—C14 | 120.0 | C56—C55—C54 | 120.0 |
C10—C9—C8 | 120.6 (3) | C56—C55—H55 | 120.0 |
C14—C9—C8 | 119.3 (3) | C54—C55—H55 | 120.0 |
C11—C10—C9 | 120.0 | C57—C56—C55 | 120.0 |
C11—C10—H10 | 120.0 | C57—C56—H56 | 120.0 |
C9—C10—H10 | 120.0 | C55—C56—H56 | 120.0 |
C10—C11—C12 | 120.0 | C56—C57—C52 | 120.0 |
C10—C11—H11 | 120.0 | C56—C57—H57 | 120.0 |
C12—C11—H11 | 120.0 | C52—C57—H57 | 120.0 |
C13—C12—C11 | 120.0 | C59—C58—C63 | 120.0 |
C13—C12—H12 | 120.0 | C59—C58—B1 | 119.7 (3) |
C11—C12—H12 | 120.0 | C63—C58—B1 | 120.3 (3) |
C12—C13—C14 | 120.0 | C60—C59—C58 | 120.0 |
C12—C13—H13 | 120.0 | C60—C59—H59 | 120.0 |
C14—C13—H13 | 120.0 | C58—C59—H59 | 120.0 |
C13—C14—C9 | 120.0 | C59—C60—C61 | 120.0 |
C13—C14—H14 | 120.0 | C59—C60—H60 | 120.0 |
C9—C14—H14 | 120.0 | C61—C60—H60 | 120.0 |
C16—C15—Sn1 | 113.7 (3) | C62—C61—C60 | 120.0 |
C16—C15—H15A | 108.8 | C62—C61—H61 | 120.0 |
Sn1—C15—H15A | 108.8 | C60—C61—H61 | 120.0 |
C16—C15—H15B | 108.8 | C61—C62—C63 | 120.0 |
Sn1—C15—H15B | 108.8 | C61—C62—H62 | 120.0 |
H15A—C15—H15B | 107.7 | C63—C62—H62 | 120.0 |
C17—C16—C21 | 120.0 | C62—C63—C58 | 120.0 |
C17—C16—C15 | 118.9 (3) | C62—C63—H63 | 120.0 |
C21—C16—C15 | 121.1 (3) | C58—C63—H63 | 120.0 |
C18—C17—C16 | 120.0 | C65—C64—C69 | 120.0 |
C18—C17—H17 | 120.0 | C65—C64—B1 | 119.1 (3) |
C16—C17—H17 | 120.0 | C69—C64—B1 | 120.9 (3) |
C17—C18—C19 | 120.0 | C66—C65—C64 | 120.0 |
C17—C18—H18 | 120.0 | C66—C65—H65 | 120.0 |
C19—C18—H18 | 120.0 | C64—C65—H65 | 120.0 |
C20—C19—C18 | 120.0 | C65—C66—C67 | 120.0 |
C20—C19—H19 | 120.0 | C65—C66—H66 | 120.0 |
C18—C19—H19 | 120.0 | C67—C66—H66 | 120.0 |
C21—C20—C19 | 120.0 | C68—C67—C66 | 120.0 |
C21—C20—H20 | 120.0 | C68—C67—H67 | 120.0 |
C19—C20—H20 | 120.0 | C66—C67—H67 | 120.0 |
C20—C21—C16 | 120.0 | C67—C68—C69 | 120.0 |
C20—C21—H21 | 120.0 | C67—C68—H68 | 120.0 |
C16—C21—H21 | 120.0 | C69—C68—H68 | 120.0 |
C23—C22—C27 | 120.0 | C68—C69—C64 | 120.0 |
C23—C22—As1 | 120.4 (2) | C68—C69—H69 | 120.0 |
C27—C22—As1 | 119.5 (2) | C64—C69—H69 | 120.0 |
C22—C23—C24 | 120.0 | C71—C70—C75 | 120.0 |
C22—C23—H23 | 120.0 | C71—C70—B1 | 119.6 (3) |
C24—C23—H23 | 120.0 | C75—C70—B1 | 120.4 (3) |
C23—C24—C25 | 120.0 | C72—C71—C70 | 120.0 |
C23—C24—H24 | 120.0 | C72—C71—H71 | 120.0 |
C25—C24—H24 | 120.0 | C70—C71—H71 | 120.0 |
C26—C25—C24 | 120.0 | C71—C72—C73 | 120.0 |
C26—C25—H25 | 120.0 | C71—C72—H72 | 120.0 |
C24—C25—H25 | 120.0 | C73—C72—H72 | 120.0 |
C25—C26—C27 | 120.0 | C72—C73—C74 | 120.0 |
C25—C26—H26 | 120.0 | C72—C73—H73 | 120.0 |
C27—C26—H26 | 120.0 | C74—C73—H73 | 120.0 |
C26—C27—C22 | 120.0 | C75—C74—C73 | 120.0 |
C26—C27—H27 | 120.0 | C75—C74—H74 | 120.0 |
C22—C27—H27 | 120.0 | C73—C74—H74 | 120.0 |
C29—C28—C33 | 120.0 | C74—C75—C70 | 120.0 |
C29—C28—As1 | 120.76 (18) | C74—C75—H75 | 120.0 |
C33—C28—As1 | 119.23 (18) | C70—C75—H75 | 120.0 |
C30—C29—C28 | 120.0 | C77—C76—C81 | 120.0 |
C30—C29—H29 | 120.0 | C77—C76—B1 | 117.6 (3) |
C28—C29—H29 | 120.0 | C81—C76—B1 | 122.4 (3) |
C29—C30—C31 | 120.0 | C76—C77—C78 | 120.0 |
C29—C30—H30 | 120.0 | C76—C77—H77 | 120.0 |
C31—C30—H30 | 120.0 | C78—C77—H77 | 120.0 |
C32—C31—C30 | 120.0 | C77—C78—C79 | 120.0 |
C32—C31—H31 | 120.0 | C77—C78—H78 | 120.0 |
C30—C31—H31 | 120.0 | C79—C78—H78 | 120.0 |
C31—C32—C33 | 120.0 | C78—C79—C80 | 120.0 |
C31—C32—H32 | 120.0 | C78—C79—H79 | 120.0 |
C33—C32—H32 | 120.0 | C80—C79—H79 | 120.0 |
C32—C33—C28 | 120.0 | C81—C80—C79 | 120.0 |
C32—C33—H33 | 120.0 | C81—C80—H80 | 120.0 |
C28—C33—H33 | 120.0 | C79—C80—H80 | 120.0 |
C35—C34—C39 | 120.0 | C80—C81—C76 | 120.0 |
C35—C34—As1 | 119.74 (19) | C80—C81—H81 | 120.0 |
C39—C34—As1 | 120.18 (19) | C76—C81—H81 | 120.0 |
C22—As1—O1—Sn1 | 126.5 (9) | C52—As2—C40—C41 | 88.5 (2) |
C34—As1—O1—Sn1 | −114.8 (9) | C46—As2—C40—C41 | −154.27 (18) |
C28—As1—O1—Sn1 | 4.8 (9) | O2—As2—C40—C45 | 148.1 (2) |
C15—Sn1—O1—As1 | 139.5 (9) | C52—As2—C40—C45 | −89.7 (2) |
C8—Sn1—O1—As1 | 13.6 (9) | C46—As2—C40—C45 | 27.6 (2) |
C1—Sn1—O1—As1 | −101.0 (9) | C45—C40—C41—C42 | 0.0 |
C40—As2—O2—Sn1 | 128.4 (6) | As2—C40—C41—C42 | −178.2 (2) |
C52—As2—O2—Sn1 | 8.4 (7) | C40—C41—C42—C43 | 0.0 |
C46—As2—O2—Sn1 | −109.8 (6) | C41—C42—C43—C44 | 0.0 |
C15—Sn1—O2—As2 | 62.7 (6) | C42—C43—C44—C45 | 0.0 |
C8—Sn1—O2—As2 | −171.2 (6) | C43—C44—C45—C40 | 0.0 |
C1—Sn1—O2—As2 | −57.0 (6) | C41—C40—C45—C44 | 0.0 |
C15—Sn1—C1—C2 | 144.6 (3) | As2—C40—C45—C44 | 178.1 (3) |
C8—Sn1—C1—C2 | −37.7 (4) | O2—As2—C46—C47 | −9.3 (2) |
O1—Sn1—C1—C2 | 57.2 (4) | C40—As2—C46—C47 | 111.3 (2) |
O2—Sn1—C1—C2 | −124.5 (3) | C52—As2—C46—C47 | −130.62 (19) |
Sn1—C1—C2—C3 | −100.8 (3) | O2—As2—C46—C51 | 172.3 (2) |
Sn1—C1—C2—C7 | 77.3 (4) | C40—As2—C46—C51 | −67.0 (2) |
C7—C2—C3—C4 | 0.0 | C52—As2—C46—C51 | 51.0 (2) |
C1—C2—C3—C4 | 178.1 (4) | C51—C46—C47—C48 | 0.0 |
C2—C3—C4—C5 | 0.0 | As2—C46—C47—C48 | −178.4 (2) |
C3—C4—C5—C6 | 0.0 | C46—C47—C48—C49 | 0.0 |
C4—C5—C6—C7 | 0.0 | C47—C48—C49—C50 | 0.0 |
C5—C6—C7—C2 | 0.0 | C48—C49—C50—C51 | 0.0 |
C3—C2—C7—C6 | 0.0 | C49—C50—C51—C46 | 0.0 |
C1—C2—C7—C6 | −178.1 (4) | C47—C46—C51—C50 | 0.0 |
C15—Sn1—C8—C9 | −4.9 (4) | As2—C46—C51—C50 | 178.3 (2) |
C1—Sn1—C8—C9 | 177.5 (3) | O2—As2—C52—C53 | −30.3 (2) |
O1—Sn1—C8—C9 | 82.7 (3) | C40—As2—C52—C53 | −150.86 (18) |
O2—Sn1—C8—C9 | −90.5 (3) | C46—As2—C52—C53 | 89.19 (19) |
Sn1—C8—C9—C10 | −91.8 (3) | O2—As2—C52—C57 | 153.30 (19) |
Sn1—C8—C9—C14 | 85.1 (3) | C40—As2—C52—C57 | 32.8 (2) |
C14—C9—C10—C11 | 0.0 | C46—As2—C52—C57 | −87.2 (2) |
C8—C9—C10—C11 | 176.9 (4) | C57—C52—C53—C54 | 0.0 |
C9—C10—C11—C12 | 0.0 | As2—C52—C53—C54 | −176.4 (2) |
C10—C11—C12—C13 | 0.0 | C52—C53—C54—C55 | 0.0 |
C11—C12—C13—C14 | 0.0 | C53—C54—C55—C56 | 0.0 |
C12—C13—C14—C9 | 0.0 | C54—C55—C56—C57 | 0.0 |
C10—C9—C14—C13 | 0.0 | C55—C56—C57—C52 | 0.0 |
C8—C9—C14—C13 | −176.9 (3) | C53—C52—C57—C56 | 0.0 |
C8—Sn1—C15—C16 | 138.9 (3) | As2—C52—C57—C56 | 176.3 (2) |
C1—Sn1—C15—C16 | −43.7 (4) | C70—B1—C58—C59 | −75.9 (4) |
O1—Sn1—C15—C16 | 47.7 (3) | C64—B1—C58—C59 | 166.1 (2) |
O2—Sn1—C15—C16 | −137.2 (3) | C76—B1—C58—C59 | 46.7 (4) |
Sn1—C15—C16—C17 | −112.3 (3) | C70—B1—C58—C63 | 101.3 (4) |
Sn1—C15—C16—C21 | 67.6 (4) | C64—B1—C58—C63 | −16.7 (4) |
C21—C16—C17—C18 | 0.0 | C76—B1—C58—C63 | −136.1 (3) |
C15—C16—C17—C18 | 179.9 (3) | C63—C58—C59—C60 | 0.0 |
C16—C17—C18—C19 | 0.0 | B1—C58—C59—C60 | 177.2 (3) |
C17—C18—C19—C20 | 0.0 | C58—C59—C60—C61 | 0.0 |
C18—C19—C20—C21 | 0.0 | C59—C60—C61—C62 | 0.0 |
C19—C20—C21—C16 | 0.0 | C60—C61—C62—C63 | 0.0 |
C17—C16—C21—C20 | 0.0 | C61—C62—C63—C58 | 0.0 |
C15—C16—C21—C20 | −179.9 (3) | C59—C58—C63—C62 | 0.0 |
O1—As1—C22—C23 | −136.7 (2) | B1—C58—C63—C62 | −177.1 (3) |
C34—As1—C22—C23 | 102.3 (2) | C58—B1—C64—C65 | 98.9 (3) |
C28—As1—C22—C23 | −14.4 (3) | C70—B1—C64—C65 | −20.0 (4) |
O1—As1—C22—C27 | 45.6 (3) | C76—B1—C64—C65 | −143.3 (3) |
C34—As1—C22—C27 | −75.4 (2) | C58—B1—C64—C69 | −79.6 (4) |
C28—As1—C22—C27 | 167.9 (2) | C70—B1—C64—C69 | 161.5 (3) |
C27—C22—C23—C24 | 0.0 | C76—B1—C64—C69 | 38.2 (4) |
As1—C22—C23—C24 | −177.7 (3) | C69—C64—C65—C66 | 0.0 |
C22—C23—C24—C25 | 0.0 | B1—C64—C65—C66 | −178.5 (3) |
C23—C24—C25—C26 | 0.0 | C64—C65—C66—C67 | 0.0 |
C24—C25—C26—C27 | 0.0 | C65—C66—C67—C68 | 0.0 |
C25—C26—C27—C22 | 0.0 | C66—C67—C68—C69 | 0.0 |
C23—C22—C27—C26 | 0.0 | C67—C68—C69—C64 | 0.0 |
As1—C22—C27—C26 | 177.7 (3) | C65—C64—C69—C68 | 0.0 |
O1—As1—C28—C29 | −135.3 (2) | B1—C64—C69—C68 | 178.5 (3) |
C22—As1—C28—C29 | 103.0 (2) | C58—B1—C70—C71 | −179.2 (3) |
C34—As1—C28—C29 | −13.5 (2) | C64—B1—C70—C71 | −61.2 (4) |
O1—As1—C28—C33 | 43.5 (2) | C76—B1—C70—C71 | 60.9 (4) |
C22—As1—C28—C33 | −78.2 (2) | C58—B1—C70—C75 | 3.6 (5) |
C34—As1—C28—C33 | 165.30 (19) | C64—B1—C70—C75 | 121.6 (3) |
C33—C28—C29—C30 | 0.0 | C76—B1—C70—C75 | −116.3 (3) |
As1—C28—C29—C30 | 178.8 (2) | C75—C70—C71—C72 | 0.0 |
C28—C29—C30—C31 | 0.0 | B1—C70—C71—C72 | −177.2 (3) |
C29—C30—C31—C32 | 0.0 | C70—C71—C72—C73 | 0.0 |
C30—C31—C32—C33 | 0.0 | C71—C72—C73—C74 | 0.0 |
C31—C32—C33—C28 | 0.0 | C72—C73—C74—C75 | 0.0 |
C29—C28—C33—C32 | 0.0 | C73—C74—C75—C70 | 0.0 |
As1—C28—C33—C32 | −178.8 (2) | C71—C70—C75—C74 | 0.0 |
O1—As1—C34—C35 | 43.5 (3) | B1—C70—C75—C74 | 177.2 (3) |
C22—As1—C34—C35 | 163.8 (2) | C58—B1—C76—C77 | 37.5 (4) |
C28—As1—C34—C35 | −78.1 (2) | C70—B1—C76—C77 | 158.5 (3) |
O1—As1—C34—C39 | −139.7 (2) | C64—B1—C76—C77 | −80.6 (4) |
C22—As1—C34—C39 | −19.5 (3) | C58—B1—C76—C81 | −142.3 (3) |
C28—As1—C34—C39 | 98.6 (2) | C70—B1—C76—C81 | −21.3 (5) |
C39—C34—C35—C36 | 0.0 | C64—B1—C76—C81 | 99.7 (4) |
As1—C34—C35—C36 | 176.7 (3) | C81—C76—C77—C78 | 0.0 |
C34—C35—C36—C37 | 0.0 | B1—C76—C77—C78 | −179.7 (4) |
C35—C36—C37—C38 | 0.0 | C76—C77—C78—C79 | 0.0 |
C36—C37—C38—C39 | 0.0 | C77—C78—C79—C80 | 0.0 |
C37—C38—C39—C34 | 0.0 | C78—C79—C80—C81 | 0.0 |
C35—C34—C39—C38 | 0.0 | C79—C80—C81—C76 | 0.0 |
As1—C34—C39—C38 | −176.7 (3) | C77—C76—C81—C80 | 0.0 |
O2—As2—C40—C41 | −33.7 (2) | B1—C76—C81—C80 | 179.7 (4) |
Experimental details
Crystal data | |
Chemical formula | [Sn(C7H7)3(C18H15AsO)](C24H20B) |
Mr | 1355.72 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 14.3288 (7), 14.9477 (7), 19.0994 (9) |
α, β, γ (°) | 69.220 (1), 73.972 (1), 62.683 (1) |
V (Å3) | 3366.4 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.40 |
Crystal size (mm) | 0.1 × 0.1 × 0.1 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (TWINABS; Bruker, 2009) |
Tmin, Tmax | 0.788, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 76329, 17932, 12383 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.170, 0.99 |
No. of reflections | 17932 |
No. of parameters | 629 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.06, −1.10 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Sn1—C1 | 2.150 (5) | Sn1—O1 | 2.175 (3) |
Sn1—C8 | 2.145 (5) | Sn1—O2 | 2.225 (3) |
Sn1—C15 | 2.144 (5) | ||
C1—Sn1—C8 | 114.4 (2) | O1—Sn1—O2 | 173.1 (1) |
C1—Sn1—C15 | 119.7 (2) | As1—O1—Sn1 | 165.3 (2) |
C8—Sn1—C15 | 125.9 (2) | As2—O2—Sn1 | 160.3 (2) |
Acknowledgements
We thank the University of Malaya (RG020/00AFr) for supporting this study.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ng, W. K., Chen, W., Kumar Das, V. G. & Butcher, R. J. (1989). J. Organomet. Chem. 361, 53–61. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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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A suggestion for improving the aqueous solubility of triorganotin(IV) compounds, R3SnX, involves exchanging the X residue by the non-nucleophilic tetraphenylborate anion to generate a salt. However, to prevent aggregation into an oligopolymer, the triorganotin species itself must be stabilized by coordination by two neutral ligands. Of the number of such compounds synthesized, the crystal structure of only one, namely, [(p-ClC6H4)Ph2Sn(Ph3AsO)2][BPh4], has been reported (Ng et al., 1989). The compound exists as non-interacting cations and anions; the tin atom of the cation is five-coordinate in a trans-C3SnO2 trigonal bipyramidal geometry. The title tribenzyltin adduct (Scheme I, Figs. 1 & 2) is a similar non-interacting salt. The trans angle at tin is nearly linear, and the Sn–O–As skeleton is also nearly linear (Table 1).