metal-organic compounds
Tribenzylchlorido(triphenylphosphine oxide-κO)tin(IV)
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
In the title tribenzylchloridotin–triphenylphosphine adduct, [Sn(C7H7)3Cl(C18H15OP)], the SnIV atom is in a trans-C3SnClO trigonal–bipyramidal geometry and is displaced out of the C3Sn girdle in the direction of the axial Cl atom by 0.112 (1) in one independent molecule and by 0.167 (1) Å in the other. The phenyl ring of one of the six benzyl units was refined as equally disordered over two sets of sites.
Related literature
For the trimethyltin chloride–triphenylphosphine adduct, see: Davis et al. (2007). For the analogous triphenyltin chloride adduct, see: de Castro et al. (2001); Eppley et al. (1992); Ng & Kumar Das (1992).
Experimental
Crystal data
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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
10.1107/S160053681101957X/zs2112sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681101957X/zs2112Isup2.hkl
Tribenzyltin chloride (0.42, 1 mmol) and triphenylphosphine oxide (0.28 g, 1 mmol) were heated in chloroform (20 ml) until the reactants dissolved completely. The filtered solution was set aside for the growth of colorless crystals, which separated after a day.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the
in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The phenyl ring of one of the six benzyl units is disordered over two positions; the occupancy could not be refined, and was assumed to be a 0.5: 0.5 type of disorder. The rings were refined as rigid hexagons of 1.39 Å sides, the Cmethylene–Cphenyl pair of distances were restrained to within ±0.01 Å of each other, and the displacement parameters of the primed atoms were set to those of the unprimed ones. The anisotropic displacement parameters were restrained to be nearly isotropic.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)3Cl(C18H15OP)] | F(000) = 2880 |
Mr = 705.81 | Dx = 1.393 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9802 reflections |
a = 10.0697 (1) Å | θ = 2.5–28.3° |
b = 31.8793 (4) Å | µ = 0.92 mm−1 |
c = 21.3259 (3) Å | T = 100 K |
β = 100.4304 (6)° | Block, colorless |
V = 6732.81 (14) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 8 |
Bruker SMART APEX diffractometer | 15456 independent reflections |
Radiation source: fine-focus sealed tube | 13210 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→12 |
Tmin = 0.771, Tmax = 0.838 | k = −41→41 |
62453 measured reflections | l = −27→27 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0298P)2 + 4.2265P] where P = (Fo2 + 2Fc2)/3 |
15456 reflections | (Δ/σ)max = 0.001 |
769 parameters | Δρmax = 0.76 e Å−3 |
37 restraints | Δρmin = −0.67 e Å−3 |
[Sn(C7H7)3Cl(C18H15OP)] | V = 6732.81 (14) Å3 |
Mr = 705.81 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0697 (1) Å | µ = 0.92 mm−1 |
b = 31.8793 (4) Å | T = 100 K |
c = 21.3259 (3) Å | 0.30 × 0.25 × 0.20 mm |
β = 100.4304 (6)° |
Bruker SMART APEX diffractometer | 15456 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 13210 reflections with I > 2σ(I) |
Tmin = 0.771, Tmax = 0.838 | Rint = 0.047 |
62453 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 37 restraints |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.76 e Å−3 |
15456 reflections | Δρmin = −0.67 e Å−3 |
769 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | 0.745692 (13) | 0.778572 (4) | 0.606789 (7) | 0.01401 (4) | |
Sn2 | 0.223618 (13) | 0.512678 (4) | 0.776274 (7) | 0.01688 (4) | |
Cl1 | 0.91606 (5) | 0.764087 (17) | 0.70807 (3) | 0.02120 (11) | |
Cl2 | 0.06400 (5) | 0.53153 (2) | 0.84882 (3) | 0.02915 (13) | |
P1 | 0.49337 (5) | 0.801792 (18) | 0.45899 (3) | 0.01764 (12) | |
P2 | 0.43088 (5) | 0.490489 (17) | 0.64836 (3) | 0.01656 (11) | |
O1 | 0.58536 (15) | 0.78523 (5) | 0.51702 (7) | 0.0214 (3) | |
O2 | 0.36436 (15) | 0.48998 (5) | 0.70558 (8) | 0.0213 (3) | |
C1 | 0.6501 (2) | 0.82902 (6) | 0.64850 (11) | 0.0176 (4) | |
H1A | 0.7135 | 0.8406 | 0.6854 | 0.021* | 0.50 |
H1B | 0.6264 | 0.8517 | 0.6168 | 0.021* | 0.50 |
H1C | 0.7078 | 0.8377 | 0.6890 | 0.021* | 0.50 |
H1D | 0.6390 | 0.8534 | 0.6193 | 0.021* | 0.50 |
C2 | 0.5231 (7) | 0.8136 (5) | 0.6703 (6) | 0.0146 (9) | 0.50 |
C3 | 0.3967 (9) | 0.8271 (4) | 0.6397 (6) | 0.0218 (9) | 0.50 |
H3 | 0.3895 | 0.8466 | 0.6056 | 0.026* | 0.50 |
C4 | 0.2809 (6) | 0.8122 (3) | 0.6592 (4) | 0.0297 (14) | 0.50 |
H4 | 0.1945 | 0.8215 | 0.6383 | 0.036* | 0.50 |
C5 | 0.2915 (5) | 0.7837 (3) | 0.7092 (3) | 0.0302 (17) | 0.50 |
H5 | 0.2123 | 0.7736 | 0.7224 | 0.036* | 0.50 |
C6 | 0.4179 (6) | 0.7702 (3) | 0.7397 (3) | 0.0252 (13) | 0.50 |
H6 | 0.4251 | 0.7507 | 0.7739 | 0.030* | 0.50 |
C7 | 0.5337 (4) | 0.7851 (4) | 0.7203 (5) | 0.0179 (12) | 0.50 |
H7 | 0.6201 | 0.7758 | 0.7412 | 0.022* | 0.50 |
C2' | 0.5136 (6) | 0.8155 (5) | 0.6611 (6) | 0.0146 (9) | 0.50 |
C3' | 0.3951 (9) | 0.8342 (4) | 0.6301 (6) | 0.0218 (9) | 0.50 |
H3' | 0.3986 | 0.8553 | 0.5989 | 0.026* | 0.50 |
C4' | 0.2716 (7) | 0.8221 (3) | 0.6447 (5) | 0.0297 (14) | 0.50 |
H4' | 0.1906 | 0.8349 | 0.6234 | 0.036* | 0.50 |
C5' | 0.2666 (5) | 0.7913 (3) | 0.6903 (3) | 0.0302 (17) | 0.50 |
H5' | 0.1822 | 0.7830 | 0.7003 | 0.036* | 0.50 |
C6' | 0.3851 (6) | 0.7726 (2) | 0.7213 (3) | 0.0252 (13) | 0.50 |
H6' | 0.3817 | 0.7515 | 0.7525 | 0.030* | 0.50 |
C7' | 0.5086 (5) | 0.7847 (4) | 0.7067 (5) | 0.0179 (12) | 0.50 |
H7' | 0.5896 | 0.7719 | 0.7280 | 0.022* | 0.50 |
C8 | 0.6655 (2) | 0.71581 (6) | 0.60576 (11) | 0.0192 (4) | |
H8A | 0.6813 | 0.7043 | 0.6496 | 0.023* | |
H8B | 0.5670 | 0.7163 | 0.5897 | 0.023* | |
C9 | 0.7327 (2) | 0.68875 (6) | 0.56402 (11) | 0.0192 (4) | |
C10 | 0.8666 (2) | 0.67583 (7) | 0.58421 (12) | 0.0220 (5) | |
H10 | 0.9137 | 0.6846 | 0.6248 | 0.026* | |
C11 | 0.9316 (2) | 0.65072 (7) | 0.54676 (13) | 0.0289 (5) | |
H11 | 1.0222 | 0.6422 | 0.5618 | 0.035* | |
C12 | 0.8653 (3) | 0.63771 (8) | 0.48707 (13) | 0.0316 (6) | |
H12 | 0.9097 | 0.6203 | 0.4612 | 0.038* | |
C13 | 0.7334 (3) | 0.65053 (8) | 0.46588 (12) | 0.0323 (6) | |
H13 | 0.6874 | 0.6420 | 0.4250 | 0.039* | |
C14 | 0.6678 (2) | 0.67567 (7) | 0.50365 (12) | 0.0251 (5) | |
H14 | 0.5774 | 0.6842 | 0.4883 | 0.030* | |
C15 | 0.9002 (2) | 0.79212 (7) | 0.55210 (11) | 0.0193 (4) | |
H15A | 0.9886 | 0.7827 | 0.5762 | 0.023* | |
H15B | 0.8815 | 0.7762 | 0.5116 | 0.023* | |
C16 | 0.90819 (19) | 0.83807 (7) | 0.53749 (11) | 0.0195 (5) | |
C17 | 0.8965 (2) | 0.85230 (8) | 0.47475 (11) | 0.0239 (5) | |
H17 | 0.8843 | 0.8327 | 0.4407 | 0.029* | |
C18 | 0.9026 (2) | 0.89505 (8) | 0.46176 (13) | 0.0323 (6) | |
H18 | 0.8943 | 0.9044 | 0.4189 | 0.039* | |
C19 | 0.9207 (2) | 0.92386 (8) | 0.51074 (14) | 0.0325 (6) | |
H19 | 0.9241 | 0.9530 | 0.5016 | 0.039* | |
C20 | 0.9340 (2) | 0.91035 (8) | 0.57303 (14) | 0.0287 (6) | |
H20 | 0.9475 | 0.9301 | 0.6069 | 0.034* | |
C21 | 0.9278 (2) | 0.86774 (7) | 0.58619 (12) | 0.0224 (5) | |
H21 | 0.9370 | 0.8587 | 0.6292 | 0.027* | |
C22 | 0.3438 (2) | 0.76998 (7) | 0.44126 (11) | 0.0206 (5) | |
C23 | 0.3007 (2) | 0.74912 (8) | 0.49142 (12) | 0.0292 (5) | |
H23 | 0.3522 | 0.7509 | 0.5333 | 0.035* | |
C24 | 0.1823 (3) | 0.72574 (9) | 0.47991 (14) | 0.0367 (6) | |
H24 | 0.1528 | 0.7114 | 0.5140 | 0.044* | |
C25 | 0.1072 (3) | 0.72329 (8) | 0.41898 (15) | 0.0365 (7) | |
H25 | 0.0266 | 0.7072 | 0.4112 | 0.044* | |
C26 | 0.1490 (2) | 0.74414 (8) | 0.36953 (13) | 0.0338 (6) | |
H26 | 0.0965 | 0.7425 | 0.3278 | 0.041* | |
C27 | 0.2671 (2) | 0.76754 (8) | 0.37998 (12) | 0.0261 (5) | |
H27 | 0.2955 | 0.7818 | 0.3456 | 0.031* | |
C28 | 0.4403 (2) | 0.85444 (7) | 0.46948 (10) | 0.0196 (4) | |
C29 | 0.3045 (2) | 0.86599 (8) | 0.46075 (11) | 0.0240 (5) | |
H29 | 0.2358 | 0.8458 | 0.4477 | 0.029* | |
C30 | 0.2704 (2) | 0.90737 (8) | 0.47138 (12) | 0.0291 (5) | |
H30 | 0.1781 | 0.9155 | 0.4651 | 0.035* | |
C31 | 0.3696 (3) | 0.93652 (8) | 0.49099 (12) | 0.0281 (5) | |
H31 | 0.3456 | 0.9647 | 0.4983 | 0.034* | |
C32 | 0.5051 (2) | 0.92508 (7) | 0.50027 (11) | 0.0256 (5) | |
H32 | 0.5732 | 0.9454 | 0.5142 | 0.031* | |
C33 | 0.5408 (2) | 0.88433 (7) | 0.48930 (11) | 0.0217 (5) | |
H33 | 0.6333 | 0.8766 | 0.4952 | 0.026* | |
C34 | 0.5789 (2) | 0.80212 (7) | 0.39232 (10) | 0.0191 (4) | |
C35 | 0.5664 (2) | 0.83505 (8) | 0.34867 (11) | 0.0256 (5) | |
H35 | 0.5041 | 0.8571 | 0.3513 | 0.031* | |
C36 | 0.6445 (3) | 0.83575 (8) | 0.30150 (12) | 0.0300 (5) | |
H36 | 0.6358 | 0.8583 | 0.2719 | 0.036* | |
C37 | 0.7348 (2) | 0.80389 (8) | 0.29743 (12) | 0.0286 (5) | |
H37 | 0.7895 | 0.8048 | 0.2655 | 0.034* | |
C38 | 0.7462 (2) | 0.77050 (8) | 0.33961 (12) | 0.0271 (5) | |
H38 | 0.8075 | 0.7483 | 0.3361 | 0.033* | |
C39 | 0.6690 (2) | 0.76942 (7) | 0.38665 (12) | 0.0233 (5) | |
H39 | 0.6768 | 0.7464 | 0.4154 | 0.028* | |
C40 | 0.0634 (2) | 0.49702 (7) | 0.69772 (11) | 0.0196 (4) | |
H40A | −0.0178 | 0.5140 | 0.7000 | 0.024* | |
H40B | 0.0923 | 0.5031 | 0.6567 | 0.024* | |
C41 | 0.0315 (2) | 0.45124 (7) | 0.70179 (10) | 0.0184 (4) | |
C42 | −0.0702 (2) | 0.43763 (7) | 0.73324 (12) | 0.0255 (5) | |
H42 | −0.1229 | 0.4577 | 0.7508 | 0.031* | |
C43 | −0.0958 (3) | 0.39515 (8) | 0.73924 (13) | 0.0330 (6) | |
H43 | −0.1661 | 0.3865 | 0.7606 | 0.040* | |
C44 | −0.0199 (3) | 0.36541 (8) | 0.71439 (12) | 0.0326 (6) | |
H44 | −0.0370 | 0.3364 | 0.7190 | 0.039* | |
C45 | 0.0811 (3) | 0.37840 (8) | 0.68280 (13) | 0.0311 (6) | |
H45 | 0.1338 | 0.3582 | 0.6655 | 0.037* | |
C46 | 0.1058 (2) | 0.42074 (7) | 0.67619 (12) | 0.0244 (5) | |
H46 | 0.1747 | 0.4292 | 0.6538 | 0.029* | |
C47 | 0.3230 (2) | 0.46353 (7) | 0.83715 (11) | 0.0224 (5) | |
H47A | 0.2881 | 0.4635 | 0.8777 | 0.027* | |
H47B | 0.3008 | 0.4361 | 0.8162 | 0.027* | |
C48 | 0.4739 (2) | 0.46884 (7) | 0.85147 (11) | 0.0199 (5) | |
C49 | 0.5328 (2) | 0.50544 (7) | 0.87912 (11) | 0.0246 (5) | |
H49 | 0.4766 | 0.5273 | 0.8897 | 0.030* | |
C50 | 0.6715 (2) | 0.51072 (8) | 0.89150 (12) | 0.0301 (6) | |
H50 | 0.7093 | 0.5363 | 0.9092 | 0.036* | |
C51 | 0.7549 (2) | 0.47891 (9) | 0.87814 (13) | 0.0329 (6) | |
H51 | 0.8502 | 0.4824 | 0.8867 | 0.040* | |
C52 | 0.6986 (2) | 0.44201 (9) | 0.85232 (12) | 0.0314 (6) | |
H52 | 0.7555 | 0.4197 | 0.8439 | 0.038* | |
C53 | 0.5594 (2) | 0.43704 (8) | 0.83842 (11) | 0.0253 (5) | |
H53 | 0.5221 | 0.4116 | 0.8198 | 0.030* | |
C54 | 0.3345 (2) | 0.57118 (7) | 0.78922 (12) | 0.0223 (5) | |
H54A | 0.3424 | 0.5795 | 0.8345 | 0.027* | |
H54B | 0.4271 | 0.5655 | 0.7818 | 0.027* | |
C55 | 0.2812 (2) | 0.60816 (7) | 0.74926 (12) | 0.0240 (5) | |
C56 | 0.1711 (2) | 0.63098 (8) | 0.76282 (14) | 0.0316 (6) | |
H56 | 0.1258 | 0.6218 | 0.7957 | 0.038* | |
C57 | 0.1275 (3) | 0.66700 (8) | 0.72840 (16) | 0.0412 (8) | |
H57 | 0.0532 | 0.6824 | 0.7382 | 0.049* | |
C58 | 0.1913 (3) | 0.68039 (8) | 0.68034 (16) | 0.0430 (8) | |
H58 | 0.1607 | 0.7050 | 0.6569 | 0.052* | |
C59 | 0.3001 (3) | 0.65814 (8) | 0.66595 (14) | 0.0399 (7) | |
H59 | 0.3442 | 0.6674 | 0.6326 | 0.048* | |
C60 | 0.3445 (2) | 0.62220 (7) | 0.70057 (13) | 0.0291 (6) | |
H60 | 0.4193 | 0.6071 | 0.6907 | 0.035* | |
C61 | 0.3140 (2) | 0.50362 (7) | 0.57643 (11) | 0.0188 (4) | |
C62 | 0.2527 (2) | 0.54308 (7) | 0.57332 (11) | 0.0230 (5) | |
H62 | 0.2761 | 0.5623 | 0.6076 | 0.028* | |
C63 | 0.1583 (2) | 0.55421 (7) | 0.52060 (12) | 0.0263 (5) | |
H63 | 0.1171 | 0.5811 | 0.5187 | 0.032* | |
C64 | 0.1233 (2) | 0.52634 (8) | 0.47043 (12) | 0.0272 (5) | |
H64 | 0.0592 | 0.5343 | 0.4340 | 0.033* | |
C65 | 0.1815 (2) | 0.48715 (8) | 0.47342 (12) | 0.0260 (5) | |
H65 | 0.1564 | 0.4679 | 0.4393 | 0.031* | |
C66 | 0.2774 (2) | 0.47558 (7) | 0.52646 (11) | 0.0210 (5) | |
H66 | 0.3175 | 0.4485 | 0.5283 | 0.025* | |
C67 | 0.5046 (2) | 0.44010 (7) | 0.63761 (11) | 0.0191 (4) | |
C68 | 0.4809 (2) | 0.40737 (7) | 0.67713 (11) | 0.0234 (5) | |
H68 | 0.4242 | 0.4116 | 0.7077 | 0.028* | |
C69 | 0.5402 (3) | 0.36846 (7) | 0.67200 (13) | 0.0304 (6) | |
H69 | 0.5253 | 0.3462 | 0.6996 | 0.036* | |
C70 | 0.6202 (2) | 0.36205 (8) | 0.62716 (13) | 0.0317 (6) | |
H70 | 0.6597 | 0.3353 | 0.6235 | 0.038* | |
C71 | 0.6435 (3) | 0.39442 (8) | 0.58721 (14) | 0.0323 (6) | |
H71 | 0.6985 | 0.3897 | 0.5561 | 0.039* | |
C72 | 0.5872 (2) | 0.43357 (7) | 0.59241 (12) | 0.0259 (5) | |
H72 | 0.6045 | 0.4559 | 0.5654 | 0.031* | |
C73 | 0.5639 (2) | 0.52880 (6) | 0.65812 (11) | 0.0180 (4) | |
C74 | 0.6488 (2) | 0.53007 (7) | 0.71749 (12) | 0.0226 (5) | |
H74 | 0.6355 | 0.5109 | 0.7499 | 0.027* | |
C75 | 0.7525 (2) | 0.55922 (8) | 0.72939 (12) | 0.0272 (5) | |
H75 | 0.8110 | 0.5598 | 0.7697 | 0.033* | |
C76 | 0.7707 (2) | 0.58743 (7) | 0.68228 (13) | 0.0281 (5) | |
H76 | 0.8411 | 0.6076 | 0.6906 | 0.034* | |
C77 | 0.6869 (2) | 0.58641 (7) | 0.62312 (13) | 0.0267 (5) | |
H77 | 0.7001 | 0.6058 | 0.5910 | 0.032* | |
C78 | 0.5839 (2) | 0.55707 (7) | 0.61074 (11) | 0.0222 (5) | |
H78 | 0.5269 | 0.5562 | 0.5701 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01355 (7) | 0.01552 (7) | 0.01280 (7) | 0.00046 (5) | 0.00199 (5) | 0.00052 (5) |
Sn2 | 0.01476 (7) | 0.01836 (7) | 0.01724 (8) | −0.00094 (5) | 0.00209 (6) | −0.00184 (6) |
Cl1 | 0.0198 (2) | 0.0239 (3) | 0.0176 (3) | −0.00029 (19) | −0.0027 (2) | 0.0027 (2) |
Cl2 | 0.0197 (2) | 0.0408 (3) | 0.0283 (3) | −0.0025 (2) | 0.0080 (2) | −0.0129 (3) |
P1 | 0.0155 (2) | 0.0235 (3) | 0.0129 (3) | 0.0010 (2) | −0.0002 (2) | 0.0011 (2) |
P2 | 0.0175 (2) | 0.0176 (3) | 0.0151 (3) | 0.00056 (19) | 0.0045 (2) | 0.0012 (2) |
O1 | 0.0207 (7) | 0.0254 (8) | 0.0156 (8) | 0.0029 (6) | −0.0034 (6) | 0.0026 (6) |
O2 | 0.0206 (7) | 0.0256 (8) | 0.0185 (8) | −0.0002 (6) | 0.0059 (6) | 0.0011 (7) |
C1 | 0.0190 (9) | 0.0179 (10) | 0.0158 (11) | 0.0001 (8) | 0.0033 (8) | −0.0019 (8) |
C2 | 0.0165 (11) | 0.0155 (14) | 0.011 (3) | 0.0012 (11) | 0.0004 (14) | −0.0034 (16) |
C3 | 0.0232 (11) | 0.022 (3) | 0.018 (3) | 0.0070 (15) | −0.0010 (14) | −0.0009 (16) |
C4 | 0.0142 (13) | 0.027 (4) | 0.043 (4) | 0.0098 (17) | −0.0069 (18) | −0.009 (3) |
C5 | 0.023 (2) | 0.026 (3) | 0.044 (5) | −0.005 (2) | 0.012 (3) | −0.009 (3) |
C6 | 0.031 (3) | 0.0271 (16) | 0.019 (4) | −0.005 (2) | 0.007 (3) | −0.001 (2) |
C7 | 0.0181 (18) | 0.0218 (12) | 0.012 (4) | 0.000 (2) | −0.003 (2) | −0.003 (2) |
C2' | 0.0165 (11) | 0.0155 (14) | 0.011 (3) | 0.0012 (11) | 0.0004 (14) | −0.0034 (16) |
C3' | 0.0232 (11) | 0.022 (3) | 0.018 (3) | 0.0070 (15) | −0.0010 (14) | −0.0009 (16) |
C4' | 0.0142 (13) | 0.027 (4) | 0.043 (4) | 0.0098 (17) | −0.0069 (18) | −0.009 (3) |
C5' | 0.023 (2) | 0.026 (3) | 0.044 (5) | −0.005 (2) | 0.012 (3) | −0.009 (3) |
C6' | 0.031 (3) | 0.0271 (16) | 0.019 (4) | −0.005 (2) | 0.007 (3) | −0.001 (2) |
C7' | 0.0181 (18) | 0.0218 (12) | 0.012 (4) | 0.000 (2) | −0.003 (2) | −0.003 (2) |
C8 | 0.0185 (10) | 0.0198 (10) | 0.0185 (11) | −0.0025 (8) | 0.0014 (9) | 0.0014 (9) |
C9 | 0.0236 (10) | 0.0145 (10) | 0.0192 (11) | −0.0029 (8) | 0.0032 (9) | 0.0029 (9) |
C10 | 0.0227 (10) | 0.0189 (10) | 0.0226 (12) | −0.0029 (8) | −0.0012 (9) | −0.0028 (9) |
C11 | 0.0249 (11) | 0.0258 (12) | 0.0347 (15) | 0.0008 (9) | 0.0023 (10) | −0.0050 (11) |
C12 | 0.0409 (14) | 0.0253 (12) | 0.0303 (14) | 0.0037 (10) | 0.0111 (12) | −0.0091 (11) |
C13 | 0.0449 (14) | 0.0266 (12) | 0.0219 (13) | 0.0008 (11) | −0.0034 (11) | −0.0063 (10) |
C14 | 0.0273 (11) | 0.0226 (11) | 0.0224 (13) | 0.0013 (9) | −0.0032 (10) | −0.0015 (10) |
C15 | 0.0173 (10) | 0.0226 (11) | 0.0186 (11) | 0.0017 (8) | 0.0050 (9) | 0.0002 (9) |
C16 | 0.0098 (9) | 0.0263 (11) | 0.0229 (12) | 0.0001 (8) | 0.0038 (8) | 0.0040 (9) |
C17 | 0.0189 (10) | 0.0324 (12) | 0.0205 (12) | −0.0018 (9) | 0.0036 (9) | 0.0041 (10) |
C18 | 0.0226 (11) | 0.0411 (15) | 0.0324 (15) | −0.0038 (10) | 0.0025 (10) | 0.0183 (12) |
C19 | 0.0204 (11) | 0.0255 (12) | 0.0512 (18) | −0.0037 (9) | 0.0048 (11) | 0.0118 (12) |
C20 | 0.0169 (10) | 0.0263 (12) | 0.0436 (16) | −0.0023 (9) | 0.0070 (10) | −0.0039 (11) |
C21 | 0.0157 (10) | 0.0277 (12) | 0.0240 (12) | −0.0004 (8) | 0.0041 (9) | 0.0003 (10) |
C22 | 0.0188 (10) | 0.0227 (11) | 0.0194 (12) | 0.0014 (8) | 0.0012 (9) | −0.0009 (9) |
C23 | 0.0225 (11) | 0.0401 (14) | 0.0235 (13) | −0.0035 (10) | 0.0005 (10) | 0.0041 (11) |
C24 | 0.0269 (12) | 0.0443 (16) | 0.0389 (17) | −0.0067 (11) | 0.0060 (12) | 0.0093 (13) |
C25 | 0.0222 (12) | 0.0379 (14) | 0.0474 (18) | −0.0073 (10) | 0.0006 (12) | −0.0036 (13) |
C26 | 0.0280 (12) | 0.0382 (14) | 0.0311 (15) | −0.0018 (10) | −0.0054 (11) | −0.0097 (12) |
C27 | 0.0235 (11) | 0.0330 (13) | 0.0209 (12) | 0.0005 (9) | 0.0017 (9) | −0.0031 (10) |
C28 | 0.0212 (10) | 0.0241 (11) | 0.0130 (11) | 0.0027 (8) | 0.0019 (8) | 0.0016 (9) |
C29 | 0.0208 (10) | 0.0321 (12) | 0.0189 (12) | 0.0015 (9) | 0.0030 (9) | 0.0006 (10) |
C30 | 0.0255 (11) | 0.0398 (14) | 0.0227 (13) | 0.0116 (10) | 0.0062 (10) | 0.0002 (11) |
C31 | 0.0405 (13) | 0.0268 (12) | 0.0188 (12) | 0.0085 (10) | 0.0101 (10) | −0.0006 (10) |
C32 | 0.0322 (12) | 0.0289 (12) | 0.0162 (12) | −0.0019 (10) | 0.0055 (10) | 0.0020 (10) |
C33 | 0.0212 (10) | 0.0278 (12) | 0.0160 (11) | 0.0009 (9) | 0.0027 (9) | 0.0029 (9) |
C34 | 0.0173 (9) | 0.0265 (11) | 0.0124 (11) | −0.0009 (8) | 0.0000 (8) | −0.0014 (9) |
C35 | 0.0284 (11) | 0.0289 (12) | 0.0199 (12) | 0.0065 (9) | 0.0051 (10) | 0.0038 (10) |
C36 | 0.0381 (13) | 0.0347 (14) | 0.0182 (13) | 0.0013 (11) | 0.0081 (11) | 0.0059 (10) |
C37 | 0.0253 (11) | 0.0421 (14) | 0.0192 (12) | −0.0029 (10) | 0.0062 (10) | −0.0070 (11) |
C38 | 0.0229 (11) | 0.0335 (13) | 0.0248 (13) | 0.0042 (9) | 0.0040 (10) | −0.0068 (11) |
C39 | 0.0232 (11) | 0.0239 (11) | 0.0219 (12) | 0.0010 (9) | 0.0019 (9) | −0.0019 (9) |
C40 | 0.0172 (9) | 0.0224 (11) | 0.0186 (11) | −0.0008 (8) | 0.0017 (8) | 0.0004 (9) |
C41 | 0.0178 (9) | 0.0221 (11) | 0.0132 (11) | −0.0010 (8) | −0.0030 (8) | −0.0025 (9) |
C42 | 0.0261 (11) | 0.0278 (12) | 0.0240 (13) | −0.0045 (9) | 0.0078 (10) | −0.0065 (10) |
C43 | 0.0440 (14) | 0.0332 (14) | 0.0243 (14) | −0.0148 (11) | 0.0123 (12) | −0.0031 (11) |
C44 | 0.0497 (15) | 0.0202 (12) | 0.0252 (14) | −0.0084 (11) | −0.0003 (12) | 0.0011 (10) |
C45 | 0.0342 (13) | 0.0250 (12) | 0.0324 (15) | 0.0029 (10) | 0.0015 (11) | −0.0068 (11) |
C46 | 0.0232 (11) | 0.0253 (12) | 0.0252 (13) | −0.0021 (9) | 0.0058 (9) | −0.0050 (10) |
C47 | 0.0181 (10) | 0.0317 (12) | 0.0166 (11) | −0.0013 (9) | 0.0009 (9) | 0.0094 (10) |
C48 | 0.0206 (10) | 0.0253 (11) | 0.0135 (11) | −0.0005 (8) | 0.0023 (8) | 0.0032 (9) |
C49 | 0.0252 (11) | 0.0270 (12) | 0.0196 (12) | 0.0021 (9) | −0.0013 (9) | 0.0016 (10) |
C50 | 0.0285 (12) | 0.0322 (13) | 0.0257 (14) | −0.0072 (10) | −0.0058 (10) | 0.0070 (11) |
C51 | 0.0190 (11) | 0.0533 (17) | 0.0263 (14) | −0.0002 (10) | 0.0034 (10) | 0.0134 (12) |
C52 | 0.0271 (12) | 0.0478 (16) | 0.0210 (13) | 0.0137 (11) | 0.0086 (10) | 0.0062 (11) |
C53 | 0.0297 (12) | 0.0280 (12) | 0.0176 (12) | 0.0046 (9) | 0.0028 (10) | 0.0008 (10) |
C54 | 0.0189 (10) | 0.0183 (10) | 0.0286 (13) | −0.0019 (8) | 0.0018 (9) | −0.0050 (9) |
C55 | 0.0221 (10) | 0.0201 (11) | 0.0269 (13) | −0.0013 (8) | −0.0036 (9) | −0.0062 (10) |
C56 | 0.0275 (12) | 0.0280 (13) | 0.0359 (15) | 0.0041 (10) | −0.0033 (11) | −0.0063 (11) |
C57 | 0.0343 (14) | 0.0275 (13) | 0.054 (2) | 0.0082 (11) | −0.0125 (14) | −0.0084 (13) |
C58 | 0.0448 (15) | 0.0201 (12) | 0.053 (2) | −0.0024 (11) | −0.0209 (15) | 0.0033 (12) |
C59 | 0.0444 (15) | 0.0313 (14) | 0.0382 (17) | −0.0124 (12) | −0.0075 (13) | 0.0047 (12) |
C60 | 0.0291 (12) | 0.0235 (12) | 0.0318 (14) | −0.0051 (9) | −0.0018 (11) | −0.0017 (10) |
C61 | 0.0183 (9) | 0.0211 (10) | 0.0173 (11) | 0.0004 (8) | 0.0045 (8) | 0.0020 (9) |
C62 | 0.0260 (11) | 0.0239 (11) | 0.0191 (12) | 0.0005 (9) | 0.0038 (9) | −0.0015 (9) |
C63 | 0.0252 (11) | 0.0256 (12) | 0.0278 (13) | 0.0069 (9) | 0.0039 (10) | 0.0029 (10) |
C64 | 0.0195 (11) | 0.0400 (14) | 0.0210 (13) | 0.0036 (9) | 0.0010 (9) | 0.0030 (11) |
C65 | 0.0233 (11) | 0.0335 (13) | 0.0206 (12) | 0.0001 (9) | 0.0025 (9) | −0.0063 (10) |
C66 | 0.0203 (10) | 0.0220 (11) | 0.0218 (12) | 0.0001 (8) | 0.0069 (9) | −0.0012 (9) |
C67 | 0.0196 (10) | 0.0179 (10) | 0.0191 (11) | 0.0012 (8) | 0.0021 (9) | 0.0017 (9) |
C68 | 0.0269 (11) | 0.0250 (11) | 0.0180 (12) | 0.0001 (9) | 0.0027 (9) | 0.0032 (9) |
C69 | 0.0359 (13) | 0.0217 (12) | 0.0312 (15) | 0.0016 (10) | −0.0002 (11) | 0.0074 (10) |
C70 | 0.0298 (12) | 0.0235 (12) | 0.0398 (16) | 0.0084 (9) | 0.0014 (11) | 0.0001 (11) |
C71 | 0.0327 (13) | 0.0272 (13) | 0.0402 (16) | 0.0066 (10) | 0.0150 (12) | 0.0000 (11) |
C72 | 0.0278 (11) | 0.0227 (11) | 0.0295 (14) | 0.0032 (9) | 0.0115 (10) | 0.0038 (10) |
C73 | 0.0178 (9) | 0.0168 (10) | 0.0206 (11) | 0.0024 (8) | 0.0067 (9) | −0.0014 (9) |
C74 | 0.0216 (10) | 0.0230 (11) | 0.0228 (12) | 0.0028 (8) | 0.0030 (9) | 0.0012 (9) |
C75 | 0.0199 (10) | 0.0325 (13) | 0.0278 (14) | 0.0000 (9) | 0.0004 (10) | −0.0052 (11) |
C76 | 0.0234 (11) | 0.0243 (12) | 0.0381 (15) | −0.0024 (9) | 0.0095 (11) | −0.0074 (11) |
C77 | 0.0313 (12) | 0.0201 (11) | 0.0314 (14) | −0.0032 (9) | 0.0127 (11) | 0.0008 (10) |
C78 | 0.0255 (11) | 0.0215 (11) | 0.0206 (12) | −0.0003 (9) | 0.0067 (9) | −0.0009 (9) |
Sn1—C1 | 2.148 (2) | C31—C32 | 1.391 (3) |
Sn1—C15 | 2.151 (2) | C31—H31 | 0.9500 |
Sn1—C8 | 2.156 (2) | C32—C33 | 1.379 (3) |
Sn1—O1 | 2.2798 (14) | C32—H32 | 0.9500 |
Sn1—Cl1 | 2.5456 (5) | C33—H33 | 0.9500 |
Sn2—C40 | 2.163 (2) | C34—C35 | 1.393 (3) |
Sn2—C47 | 2.161 (2) | C34—C39 | 1.402 (3) |
Sn2—C54 | 2.165 (2) | C35—C36 | 1.385 (3) |
Sn2—O2 | 2.3618 (16) | C35—H35 | 0.9500 |
Sn2—Cl2 | 2.4977 (6) | C36—C37 | 1.376 (4) |
P1—O1 | 1.5011 (15) | C36—H36 | 0.9500 |
P1—C28 | 1.788 (2) | C37—C38 | 1.385 (4) |
P1—C34 | 1.791 (2) | C37—H37 | 0.9500 |
P1—C22 | 1.798 (2) | C38—C39 | 1.377 (4) |
P2—O2 | 1.4947 (17) | C38—H38 | 0.9500 |
P2—C73 | 1.797 (2) | C39—H39 | 0.9500 |
P2—C67 | 1.802 (2) | C40—C41 | 1.500 (3) |
P2—C61 | 1.806 (2) | C40—H40A | 0.9900 |
C1—C2' | 1.510 (5) | C40—H40B | 0.9900 |
C1—C2 | 1.520 (5) | C41—C42 | 1.391 (3) |
C1—H1A | 0.9900 | C41—C46 | 1.397 (3) |
C1—H1B | 0.9900 | C42—C43 | 1.389 (3) |
C1—H1C | 0.9900 | C42—H42 | 0.9500 |
C1—H1D | 0.9900 | C43—C44 | 1.382 (4) |
C2—C3 | 1.3900 | C43—H43 | 0.9500 |
C2—C7 | 1.3900 | C44—C45 | 1.381 (4) |
C3—C4 | 1.3900 | C44—H44 | 0.9500 |
C3—H3 | 0.9500 | C45—C46 | 1.384 (3) |
C4—C5 | 1.3900 | C45—H45 | 0.9500 |
C4—H4 | 0.9500 | C46—H46 | 0.9500 |
C5—C6 | 1.3900 | C47—C48 | 1.504 (3) |
C5—H5 | 0.9500 | C47—H47A | 0.9900 |
C6—C7 | 1.3900 | C47—H47B | 0.9900 |
C6—H6 | 0.9500 | C48—C49 | 1.391 (3) |
C7—H7 | 0.9500 | C48—C53 | 1.391 (3) |
C2'—C3' | 1.3900 | C49—C50 | 1.384 (3) |
C2'—C7' | 1.3900 | C49—H49 | 0.9500 |
C3'—C4' | 1.3900 | C50—C51 | 1.379 (4) |
C3'—H3' | 0.9500 | C50—H50 | 0.9500 |
C4'—C5' | 1.3900 | C51—C52 | 1.377 (4) |
C4'—H4' | 0.9500 | C51—H51 | 0.9500 |
C5'—C6' | 1.3900 | C52—C53 | 1.388 (3) |
C5'—H5' | 0.9500 | C52—H52 | 0.9500 |
C6'—C7' | 1.3900 | C53—H53 | 0.9500 |
C6'—H6' | 0.9500 | C54—C55 | 1.496 (3) |
C7'—H7' | 0.9500 | C54—H54A | 0.9900 |
C8—C9 | 1.487 (3) | C54—H54B | 0.9900 |
C8—H8A | 0.9900 | C55—C60 | 1.387 (4) |
C8—H8B | 0.9900 | C55—C56 | 1.400 (3) |
C9—C14 | 1.398 (3) | C56—C57 | 1.390 (4) |
C9—C10 | 1.401 (3) | C56—H56 | 0.9500 |
C10—C11 | 1.377 (3) | C57—C58 | 1.372 (5) |
C10—H10 | 0.9500 | C57—H57 | 0.9500 |
C11—C12 | 1.389 (3) | C58—C59 | 1.386 (4) |
C11—H11 | 0.9500 | C58—H58 | 0.9500 |
C12—C13 | 1.384 (4) | C59—C60 | 1.392 (4) |
C12—H12 | 0.9500 | C59—H59 | 0.9500 |
C13—C14 | 1.386 (4) | C60—H60 | 0.9500 |
C13—H13 | 0.9500 | C61—C66 | 1.389 (3) |
C14—H14 | 0.9500 | C61—C62 | 1.398 (3) |
C15—C16 | 1.503 (3) | C62—C63 | 1.381 (3) |
C15—H15A | 0.9900 | C62—H62 | 0.9500 |
C15—H15B | 0.9900 | C63—C64 | 1.386 (3) |
C16—C21 | 1.392 (3) | C63—H63 | 0.9500 |
C16—C17 | 1.397 (3) | C64—C65 | 1.376 (3) |
C17—C18 | 1.394 (3) | C64—H64 | 0.9500 |
C17—H17 | 0.9500 | C65—C66 | 1.397 (3) |
C18—C19 | 1.378 (4) | C65—H65 | 0.9500 |
C18—H18 | 0.9500 | C66—H66 | 0.9500 |
C19—C20 | 1.380 (4) | C67—C68 | 1.389 (3) |
C19—H19 | 0.9500 | C67—C72 | 1.398 (3) |
C20—C21 | 1.391 (3) | C68—C69 | 1.389 (3) |
C20—H20 | 0.9500 | C68—H68 | 0.9500 |
C21—H21 | 0.9500 | C69—C70 | 1.373 (4) |
C22—C23 | 1.394 (3) | C69—H69 | 0.9500 |
C22—C27 | 1.394 (3) | C70—C71 | 1.385 (4) |
C23—C24 | 1.390 (3) | C70—H70 | 0.9500 |
C23—H23 | 0.9500 | C71—C72 | 1.384 (3) |
C24—C25 | 1.382 (4) | C71—H71 | 0.9500 |
C24—H24 | 0.9500 | C72—H72 | 0.9500 |
C25—C26 | 1.375 (4) | C73—C74 | 1.394 (3) |
C25—H25 | 0.9500 | C73—C78 | 1.395 (3) |
C26—C27 | 1.387 (3) | C74—C75 | 1.387 (3) |
C26—H26 | 0.9500 | C74—H74 | 0.9500 |
C27—H27 | 0.9500 | C75—C76 | 1.385 (4) |
C28—C29 | 1.395 (3) | C75—H75 | 0.9500 |
C28—C33 | 1.399 (3) | C76—C77 | 1.385 (4) |
C29—C30 | 1.392 (3) | C76—H76 | 0.9500 |
C29—H29 | 0.9500 | C77—C78 | 1.387 (3) |
C30—C31 | 1.373 (4) | C77—H77 | 0.9500 |
C30—H30 | 0.9500 | C78—H78 | 0.9500 |
C1—Sn1—C15 | 119.79 (8) | C28—C29—H29 | 120.2 |
C1—Sn1—C8 | 120.26 (8) | C31—C30—C29 | 120.2 (2) |
C15—Sn1—C8 | 119.15 (9) | C31—C30—H30 | 119.9 |
C1—Sn1—O1 | 88.60 (7) | C29—C30—H30 | 119.9 |
C15—Sn1—O1 | 89.88 (7) | C30—C31—C32 | 120.5 (2) |
C8—Sn1—O1 | 82.59 (7) | C30—C31—H31 | 119.8 |
C1—Sn1—Cl1 | 93.91 (6) | C32—C31—H31 | 119.8 |
C15—Sn1—Cl1 | 93.09 (6) | C33—C32—C31 | 120.1 (2) |
C8—Sn1—Cl1 | 91.94 (6) | C33—C32—H32 | 120.0 |
O1—Sn1—Cl1 | 174.52 (4) | C31—C32—H32 | 120.0 |
C40—Sn2—C47 | 119.81 (8) | C32—C33—C28 | 119.8 (2) |
C40—Sn2—C54 | 126.34 (8) | C32—C33—H33 | 120.1 |
C47—Sn2—C54 | 112.08 (8) | C28—C33—H33 | 120.1 |
C40—Sn2—O2 | 83.37 (7) | C35—C34—C39 | 119.0 (2) |
C47—Sn2—O2 | 84.00 (8) | C35—C34—P1 | 122.46 (18) |
C54—Sn2—O2 | 89.43 (8) | C39—C34—P1 | 118.42 (18) |
C40—Sn2—Cl2 | 93.55 (6) | C36—C35—C34 | 120.2 (2) |
C47—Sn2—Cl2 | 94.71 (7) | C36—C35—H35 | 119.9 |
C54—Sn2—Cl2 | 95.08 (7) | C34—C35—H35 | 119.9 |
O2—Sn2—Cl2 | 175.46 (4) | C37—C36—C35 | 120.1 (2) |
O1—P1—C28 | 112.39 (10) | C37—C36—H36 | 119.9 |
O1—P1—C34 | 110.06 (10) | C35—C36—H36 | 119.9 |
C28—P1—C34 | 106.95 (11) | C36—C37—C38 | 120.3 (2) |
O1—P1—C22 | 110.08 (10) | C36—C37—H37 | 119.8 |
C28—P1—C22 | 107.31 (10) | C38—C37—H37 | 119.8 |
C34—P1—C22 | 109.95 (11) | C39—C38—C37 | 120.1 (2) |
O2—P2—C73 | 110.35 (10) | C39—C38—H38 | 120.0 |
O2—P2—C67 | 110.50 (10) | C37—C38—H38 | 120.0 |
C73—P2—C67 | 107.75 (10) | C38—C39—C34 | 120.3 (2) |
O2—P2—C61 | 112.13 (10) | C38—C39—H39 | 119.9 |
C73—P2—C61 | 107.37 (10) | C34—C39—H39 | 119.9 |
C67—P2—C61 | 108.59 (10) | C41—C40—Sn2 | 108.50 (13) |
P1—O1—Sn1 | 164.27 (10) | C41—C40—H40A | 110.0 |
P2—O2—Sn2 | 158.00 (9) | Sn2—C40—H40A | 110.0 |
C2'—C1—Sn1 | 110.5 (7) | C41—C40—H40B | 110.0 |
C2—C1—Sn1 | 110.4 (7) | Sn2—C40—H40B | 110.0 |
C2'—C1—H1A | 116.2 | H40A—C40—H40B | 108.4 |
C2—C1—H1A | 109.6 | C42—C41—C46 | 117.7 (2) |
Sn1—C1—H1A | 109.6 | C42—C41—C40 | 121.0 (2) |
C2'—C1—H1B | 102.5 | C46—C41—C40 | 121.3 (2) |
C2—C1—H1B | 109.6 | C43—C42—C41 | 120.9 (2) |
Sn1—C1—H1B | 109.6 | C43—C42—H42 | 119.5 |
H1A—C1—H1B | 108.1 | C41—C42—H42 | 119.5 |
C2'—C1—H1C | 109.6 | C44—C43—C42 | 120.6 (2) |
C2—C1—H1C | 102.6 | C44—C43—H43 | 119.7 |
Sn1—C1—H1C | 109.6 | C42—C43—H43 | 119.7 |
C2'—C1—H1D | 109.6 | C43—C44—C45 | 119.2 (2) |
C2—C1—H1D | 116.3 | C43—C44—H44 | 120.4 |
Sn1—C1—H1D | 109.6 | C45—C44—H44 | 120.4 |
H1C—C1—H1D | 108.1 | C46—C45—C44 | 120.3 (2) |
C3—C2—C7 | 120.0 | C46—C45—H45 | 119.9 |
C3—C2—C1 | 120.3 (6) | C44—C45—H45 | 119.9 |
C7—C2—C1 | 119.7 (7) | C45—C46—C41 | 121.3 (2) |
C2—C3—C4 | 120.0 | C45—C46—H46 | 119.3 |
C2—C3—H3 | 120.0 | C41—C46—H46 | 119.3 |
C4—C3—H3 | 120.0 | C48—C47—Sn2 | 112.40 (15) |
C5—C4—C3 | 120.0 | C48—C47—H47A | 109.1 |
C5—C4—H4 | 120.0 | Sn2—C47—H47A | 109.1 |
C3—C4—H4 | 120.0 | C48—C47—H47B | 109.1 |
C4—C5—C6 | 120.0 | Sn2—C47—H47B | 109.1 |
C4—C5—H5 | 120.0 | H47A—C47—H47B | 107.9 |
C6—C5—H5 | 120.0 | C49—C48—C53 | 117.7 (2) |
C5—C6—C7 | 120.0 | C49—C48—C47 | 121.2 (2) |
C5—C6—H6 | 120.0 | C53—C48—C47 | 121.1 (2) |
C7—C6—H6 | 120.0 | C50—C49—C48 | 121.4 (2) |
C6—C7—C2 | 120.0 | C50—C49—H49 | 119.3 |
C6—C7—H7 | 120.0 | C48—C49—H49 | 119.3 |
C2—C7—H7 | 120.0 | C51—C50—C49 | 120.2 (2) |
C3'—C2'—C7' | 120.0 | C51—C50—H50 | 119.9 |
C3'—C2'—C1 | 121.5 (7) | C49—C50—H50 | 119.9 |
C7'—C2'—C1 | 118.4 (7) | C52—C51—C50 | 119.2 (2) |
C2'—C3'—C4' | 120.0 | C52—C51—H51 | 120.4 |
C2'—C3'—H3' | 120.0 | C50—C51—H51 | 120.4 |
C4'—C3'—H3' | 120.0 | C51—C52—C53 | 120.7 (2) |
C3'—C4'—C5' | 120.0 | C51—C52—H52 | 119.7 |
C3'—C4'—H4' | 120.0 | C53—C52—H52 | 119.7 |
C5'—C4'—H4' | 120.0 | C48—C53—C52 | 120.8 (2) |
C6'—C5'—C4' | 120.0 | C48—C53—H53 | 119.6 |
C6'—C5'—H5' | 120.0 | C52—C53—H53 | 119.6 |
C4'—C5'—H5' | 120.0 | C55—C54—Sn2 | 118.86 (14) |
C5'—C6'—C7' | 120.0 | C55—C54—H54A | 107.6 |
C5'—C6'—H6' | 120.0 | Sn2—C54—H54A | 107.6 |
C7'—C6'—H6' | 120.0 | C55—C54—H54B | 107.6 |
C6'—C7'—C2' | 120.0 | Sn2—C54—H54B | 107.6 |
C6'—C7'—H7' | 120.0 | H54A—C54—H54B | 107.0 |
C2'—C7'—H7' | 120.0 | C60—C55—C56 | 118.4 (2) |
C9—C8—Sn1 | 109.53 (14) | C60—C55—C54 | 121.0 (2) |
C9—C8—H8A | 109.8 | C56—C55—C54 | 120.5 (2) |
Sn1—C8—H8A | 109.8 | C57—C56—C55 | 120.4 (3) |
C9—C8—H8B | 109.8 | C57—C56—H56 | 119.8 |
Sn1—C8—H8B | 109.8 | C55—C56—H56 | 119.8 |
H8A—C8—H8B | 108.2 | C58—C57—C56 | 120.4 (3) |
C14—C9—C10 | 117.3 (2) | C58—C57—H57 | 119.8 |
C14—C9—C8 | 122.5 (2) | C56—C57—H57 | 119.8 |
C10—C9—C8 | 120.2 (2) | C57—C58—C59 | 120.1 (3) |
C11—C10—C9 | 121.6 (2) | C57—C58—H58 | 119.9 |
C11—C10—H10 | 119.2 | C59—C58—H58 | 119.9 |
C9—C10—H10 | 119.2 | C58—C59—C60 | 119.7 (3) |
C10—C11—C12 | 120.3 (2) | C58—C59—H59 | 120.2 |
C10—C11—H11 | 119.8 | C60—C59—H59 | 120.2 |
C12—C11—H11 | 119.8 | C55—C60—C59 | 121.1 (3) |
C11—C12—C13 | 119.0 (2) | C55—C60—H60 | 119.5 |
C11—C12—H12 | 120.5 | C59—C60—H60 | 119.5 |
C13—C12—H12 | 120.5 | C66—C61—C62 | 119.3 (2) |
C12—C13—C14 | 120.7 (2) | C66—C61—P2 | 123.00 (17) |
C12—C13—H13 | 119.6 | C62—C61—P2 | 117.60 (17) |
C14—C13—H13 | 119.6 | C63—C62—C61 | 120.2 (2) |
C13—C14—C9 | 121.0 (2) | C63—C62—H62 | 119.9 |
C13—C14—H14 | 119.5 | C61—C62—H62 | 119.9 |
C9—C14—H14 | 119.5 | C62—C63—C64 | 120.3 (2) |
C16—C15—Sn1 | 112.28 (14) | C62—C63—H63 | 119.8 |
C16—C15—H15A | 109.1 | C64—C63—H63 | 119.8 |
Sn1—C15—H15A | 109.1 | C65—C64—C63 | 120.0 (2) |
C16—C15—H15B | 109.1 | C65—C64—H64 | 120.0 |
Sn1—C15—H15B | 109.1 | C63—C64—H64 | 120.0 |
H15A—C15—H15B | 107.9 | C64—C65—C66 | 120.2 (2) |
C21—C16—C17 | 118.0 (2) | C64—C65—H65 | 119.9 |
C21—C16—C15 | 120.9 (2) | C66—C65—H65 | 119.9 |
C17—C16—C15 | 121.1 (2) | C61—C66—C65 | 120.0 (2) |
C18—C17—C16 | 120.6 (2) | C61—C66—H66 | 120.0 |
C18—C17—H17 | 119.7 | C65—C66—H66 | 120.0 |
C16—C17—H17 | 119.7 | C68—C67—C72 | 119.7 (2) |
C19—C18—C17 | 120.4 (2) | C68—C67—P2 | 118.18 (18) |
C19—C18—H18 | 119.8 | C72—C67—P2 | 122.07 (17) |
C17—C18—H18 | 119.8 | C69—C68—C67 | 120.0 (2) |
C18—C19—C20 | 119.9 (2) | C69—C68—H68 | 120.0 |
C18—C19—H19 | 120.1 | C67—C68—H68 | 120.0 |
C20—C19—H19 | 120.1 | C70—C69—C68 | 120.2 (2) |
C19—C20—C21 | 119.9 (2) | C70—C69—H69 | 119.9 |
C19—C20—H20 | 120.0 | C68—C69—H69 | 119.9 |
C21—C20—H20 | 120.0 | C69—C70—C71 | 120.3 (2) |
C16—C21—C20 | 121.2 (2) | C69—C70—H70 | 119.9 |
C16—C21—H21 | 119.4 | C71—C70—H70 | 119.9 |
C20—C21—H21 | 119.4 | C72—C71—C70 | 120.3 (3) |
C23—C22—C27 | 119.7 (2) | C72—C71—H71 | 119.8 |
C23—C22—P1 | 118.21 (17) | C70—C71—H71 | 119.8 |
C27—C22—P1 | 121.96 (19) | C71—C72—C67 | 119.6 (2) |
C22—C23—C24 | 119.8 (2) | C71—C72—H72 | 120.2 |
C22—C23—H23 | 120.1 | C67—C72—H72 | 120.2 |
C24—C23—H23 | 120.1 | C74—C73—C78 | 119.6 (2) |
C25—C24—C23 | 120.1 (3) | C74—C73—P2 | 116.53 (17) |
C25—C24—H24 | 119.9 | C78—C73—P2 | 123.84 (17) |
C23—C24—H24 | 119.9 | C75—C74—C73 | 120.2 (2) |
C26—C25—C24 | 120.2 (2) | C75—C74—H74 | 119.9 |
C26—C25—H25 | 119.9 | C73—C74—H74 | 119.9 |
C24—C25—H25 | 119.9 | C76—C75—C74 | 119.8 (2) |
C25—C26—C27 | 120.6 (2) | C76—C75—H75 | 120.1 |
C25—C26—H26 | 119.7 | C74—C75—H75 | 120.1 |
C27—C26—H26 | 119.7 | C75—C76—C77 | 120.5 (2) |
C26—C27—C22 | 119.6 (2) | C75—C76—H76 | 119.8 |
C26—C27—H27 | 120.2 | C77—C76—H76 | 119.8 |
C22—C27—H27 | 120.2 | C78—C77—C76 | 120.0 (2) |
C29—C28—C33 | 119.9 (2) | C78—C77—H77 | 120.0 |
C29—C28—P1 | 122.62 (17) | C76—C77—H77 | 120.0 |
C33—C28—P1 | 117.44 (16) | C77—C78—C73 | 119.9 (2) |
C30—C29—C28 | 119.5 (2) | C77—C78—H78 | 120.0 |
C30—C29—H29 | 120.2 | C73—C78—H78 | 120.0 |
C28—P1—O1—Sn1 | −36.3 (4) | P1—C28—C33—C32 | −177.74 (18) |
C34—P1—O1—Sn1 | 82.8 (4) | O1—P1—C34—C35 | −139.12 (18) |
C22—P1—O1—Sn1 | −155.9 (4) | C28—P1—C34—C35 | −16.8 (2) |
C1—Sn1—O1—P1 | 55.3 (4) | C22—P1—C34—C35 | 99.5 (2) |
C15—Sn1—O1—P1 | −64.5 (4) | O1—P1—C34—C39 | 36.24 (19) |
C8—Sn1—O1—P1 | 176.0 (4) | C28—P1—C34—C39 | 158.60 (17) |
C73—P2—O2—Sn2 | 76.2 (3) | C22—P1—C34—C39 | −85.20 (18) |
C67—P2—O2—Sn2 | −164.7 (2) | C39—C34—C35—C36 | −1.6 (3) |
C61—P2—O2—Sn2 | −43.4 (3) | P1—C34—C35—C36 | 173.77 (18) |
C40—Sn2—O2—P2 | 67.7 (3) | C34—C35—C36—C37 | 0.1 (4) |
C47—Sn2—O2—P2 | −171.3 (3) | C35—C36—C37—C38 | 1.3 (4) |
C54—Sn2—O2—P2 | −59.0 (3) | C36—C37—C38—C39 | −1.2 (4) |
C15—Sn1—C1—C2' | 157.5 (5) | C37—C38—C39—C34 | −0.3 (3) |
C8—Sn1—C1—C2' | −12.1 (5) | C35—C34—C39—C38 | 1.6 (3) |
O1—Sn1—C1—C2' | 68.4 (5) | P1—C34—C39—C38 | −173.88 (17) |
Cl1—Sn1—C1—C2' | −106.7 (5) | C47—Sn2—C40—C41 | 6.89 (19) |
C15—Sn1—C1—C2 | 166.0 (4) | C54—Sn2—C40—C41 | 170.44 (14) |
C8—Sn1—C1—C2 | −3.6 (5) | O2—Sn2—C40—C41 | 86.06 (15) |
O1—Sn1—C1—C2 | 77.0 (5) | Cl2—Sn2—C40—C41 | −90.60 (15) |
Cl1—Sn1—C1—C2 | −98.2 (4) | Sn2—C40—C41—C42 | 93.2 (2) |
C2'—C1—C2—C3 | −20 (9) | Sn2—C40—C41—C46 | −84.5 (2) |
Sn1—C1—C2—C3 | −112.1 (6) | C46—C41—C42—C43 | 0.5 (3) |
C2'—C1—C2—C7 | 159 (10) | C40—C41—C42—C43 | −177.3 (2) |
Sn1—C1—C2—C7 | 66.7 (9) | C41—C42—C43—C44 | 0.4 (4) |
C7—C2—C3—C4 | 0.0 | C42—C43—C44—C45 | −0.7 (4) |
C1—C2—C3—C4 | 178.7 (13) | C43—C44—C45—C46 | 0.0 (4) |
C2—C3—C4—C5 | 0.0 | C44—C45—C46—C41 | 0.9 (4) |
C3—C4—C5—C6 | 0.0 | C42—C41—C46—C45 | −1.2 (3) |
C4—C5—C6—C7 | 0.0 | C40—C41—C46—C45 | 176.6 (2) |
C5—C6—C7—C2 | 0.0 | C40—Sn2—C47—C48 | 136.09 (16) |
C3—C2—C7—C6 | 0.0 | C54—Sn2—C47—C48 | −29.7 (2) |
C1—C2—C7—C6 | −178.8 (13) | O2—Sn2—C47—C48 | 57.29 (16) |
C2—C1—C2'—C3' | 153 (10) | Cl2—Sn2—C47—C48 | −127.08 (16) |
Sn1—C1—C2'—C3' | −116.1 (6) | Sn2—C47—C48—C49 | 56.6 (3) |
C2—C1—C2'—C7' | −25 (9) | Sn2—C47—C48—C53 | −124.4 (2) |
Sn1—C1—C2'—C7' | 66.4 (9) | C53—C48—C49—C50 | 1.9 (4) |
C7'—C2'—C3'—C4' | 0.0 | C47—C48—C49—C50 | −179.0 (2) |
C1—C2'—C3'—C4' | −177.4 (13) | C48—C49—C50—C51 | −1.9 (4) |
C2'—C3'—C4'—C5' | 0.0 | C49—C50—C51—C52 | 0.1 (4) |
C3'—C4'—C5'—C6' | 0.0 | C50—C51—C52—C53 | 1.5 (4) |
C4'—C5'—C6'—C7' | 0.0 | C49—C48—C53—C52 | −0.4 (4) |
C5'—C6'—C7'—C2' | 0.0 | C47—C48—C53—C52 | −179.4 (2) |
C3'—C2'—C7'—C6' | 0.0 | C51—C52—C53—C48 | −1.4 (4) |
C1—C2'—C7'—C6' | 177.5 (12) | C40—Sn2—C54—C55 | 13.7 (2) |
C1—Sn1—C8—C9 | 169.36 (13) | C47—Sn2—C54—C55 | 178.34 (18) |
C15—Sn1—C8—C9 | −0.35 (17) | O2—Sn2—C54—C55 | 95.06 (19) |
O1—Sn1—C8—C9 | 85.35 (14) | Cl2—Sn2—C54—C55 | −84.48 (19) |
Cl1—Sn1—C8—C9 | −94.97 (14) | Sn2—C54—C55—C60 | −107.8 (2) |
Sn1—C8—C9—C14 | −105.9 (2) | Sn2—C54—C55—C56 | 76.2 (3) |
Sn1—C8—C9—C10 | 73.1 (2) | C60—C55—C56—C57 | −0.5 (3) |
C14—C9—C10—C11 | −1.0 (3) | C54—C55—C56—C57 | 175.6 (2) |
C8—C9—C10—C11 | 179.9 (2) | C55—C56—C57—C58 | 0.6 (4) |
C9—C10—C11—C12 | 0.5 (4) | C56—C57—C58—C59 | −0.3 (4) |
C10—C11—C12—C13 | 0.3 (4) | C57—C58—C59—C60 | −0.1 (4) |
C11—C12—C13—C14 | −0.5 (4) | C56—C55—C60—C59 | 0.1 (3) |
C12—C13—C14—C9 | 0.0 (4) | C54—C55—C60—C59 | −176.0 (2) |
C10—C9—C14—C13 | 0.8 (3) | C58—C59—C60—C55 | 0.2 (4) |
C8—C9—C14—C13 | 179.9 (2) | O2—P2—C61—C66 | −114.19 (19) |
C1—Sn1—C15—C16 | −11.30 (18) | C73—P2—C61—C66 | 124.44 (19) |
C8—Sn1—C15—C16 | 158.45 (14) | C67—P2—C61—C66 | 8.2 (2) |
O1—Sn1—C15—C16 | 77.02 (15) | O2—P2—C61—C62 | 62.0 (2) |
Cl1—Sn1—C15—C16 | −107.59 (14) | C73—P2—C61—C62 | −59.4 (2) |
Sn1—C15—C16—C21 | 56.0 (2) | C67—P2—C61—C62 | −175.61 (17) |
Sn1—C15—C16—C17 | −124.15 (18) | C66—C61—C62—C63 | −1.0 (3) |
C21—C16—C17—C18 | −0.8 (3) | P2—C61—C62—C63 | −177.34 (19) |
C15—C16—C17—C18 | 179.3 (2) | C61—C62—C63—C64 | 0.1 (4) |
C16—C17—C18—C19 | 0.2 (3) | C62—C63—C64—C65 | 0.9 (4) |
C17—C18—C19—C20 | 0.5 (4) | C63—C64—C65—C66 | −1.0 (4) |
C18—C19—C20—C21 | −0.6 (3) | C62—C61—C66—C65 | 0.9 (3) |
C17—C16—C21—C20 | 0.7 (3) | P2—C61—C66—C65 | 177.00 (18) |
C15—C16—C21—C20 | −179.42 (19) | C64—C65—C66—C61 | 0.1 (4) |
C19—C20—C21—C16 | 0.0 (3) | O2—P2—C67—C68 | 6.2 (2) |
O1—P1—C22—C23 | 27.9 (2) | C73—P2—C67—C68 | 126.80 (18) |
C28—P1—C22—C23 | −94.7 (2) | C61—P2—C67—C68 | −117.20 (18) |
C34—P1—C22—C23 | 149.28 (19) | O2—P2—C67—C72 | −171.92 (18) |
O1—P1—C22—C27 | −155.58 (19) | C73—P2—C67—C72 | −51.3 (2) |
C28—P1—C22—C27 | 81.8 (2) | C61—P2—C67—C72 | 64.7 (2) |
C34—P1—C22—C27 | −34.2 (2) | C72—C67—C68—C69 | 0.6 (3) |
C27—C22—C23—C24 | 0.5 (4) | P2—C67—C68—C69 | −177.55 (17) |
P1—C22—C23—C24 | 177.2 (2) | C67—C68—C69—C70 | −1.2 (3) |
C22—C23—C24—C25 | −0.2 (4) | C68—C69—C70—C71 | 0.7 (4) |
C23—C24—C25—C26 | −0.4 (4) | C69—C70—C71—C72 | 0.4 (4) |
C24—C25—C26—C27 | 0.5 (4) | C70—C71—C72—C67 | −1.0 (4) |
C25—C26—C27—C22 | −0.2 (4) | C68—C67—C72—C71 | 0.5 (3) |
C23—C22—C27—C26 | −0.4 (4) | P2—C67—C72—C71 | 178.57 (19) |
P1—C22—C27—C26 | −176.88 (19) | O2—P2—C73—C74 | 43.85 (19) |
O1—P1—C28—C29 | −124.5 (2) | C67—P2—C73—C74 | −76.87 (19) |
C34—P1—C28—C29 | 114.6 (2) | C61—P2—C73—C74 | 166.33 (17) |
C22—P1—C28—C29 | −3.3 (2) | O2—P2—C73—C78 | −134.83 (19) |
O1—P1—C28—C33 | 53.3 (2) | C67—P2—C73—C78 | 104.4 (2) |
C34—P1—C28—C33 | −67.6 (2) | C61—P2—C73—C78 | −12.4 (2) |
C22—P1—C28—C33 | 174.49 (18) | C78—C73—C74—C75 | −0.1 (3) |
C33—C28—C29—C30 | 0.6 (4) | P2—C73—C74—C75 | −178.84 (18) |
P1—C28—C29—C30 | 178.30 (18) | C73—C74—C75—C76 | 0.7 (3) |
C28—C29—C30—C31 | −0.7 (4) | C74—C75—C76—C77 | −0.8 (4) |
C29—C30—C31—C32 | 0.2 (4) | C75—C76—C77—C78 | 0.1 (4) |
C30—C31—C32—C33 | 0.5 (4) | C76—C77—C78—C73 | 0.5 (3) |
C31—C32—C33—C28 | −0.7 (4) | C74—C73—C78—C77 | −0.5 (3) |
C29—C28—C33—C32 | 0.1 (3) | P2—C73—C78—C77 | 178.10 (18) |
Experimental details
Crystal data | |
Chemical formula | [Sn(C7H7)3Cl(C18H15OP)] |
Mr | 705.81 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 10.0697 (1), 31.8793 (4), 21.3259 (3) |
β (°) | 100.4304 (6) |
V (Å3) | 6732.81 (14) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.92 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.771, 0.838 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 62453, 15456, 13210 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.072, 1.03 |
No. of reflections | 15456 |
No. of parameters | 769 |
No. of restraints | 37 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.76, −0.67 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Acknowledgements
We thank the University of Malaya (RG020/09/AFR) for supporting this study.
References
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Triorganotin halides, being strong Lewis acids, form a large number of adducts with oxygen-donor ligands. With triphenylphosphine oxide in particular, the crystal structures of the adducts with trimethyltin chloride (Davis et al., 2007) and triphenyltin chloride (de Castro et al., 2001; Eppley et al., 1992; Ng & Kumar Das, 1992) have been reported. The tribenzylchloridotin–triphenylphosphine adduct (Scheme I) has the SnIV atom in a trans-C3SnClO trigonal bipyramidal geometry. The Sn atom is displaced out of the C3Sn girdle in the direction of the axial Cl atom [by 0.112 (1) Å in one independent molecule (Fig. 1) and by 0.167 (1) Å in the other independent molecule (Fig. 2)].