Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Tris(2-methyl-2-phenylpropyl)(pyridine-3-carboxylato)tin(IV)
Lai-Jin Tian,a* Yu-Xi Sun,aMin Yangaand Guo-Ming Yangb
a
Department of Chemistry, Qufu Normal University, Qufu 273165, Shandong, People’s Republic of China, andbDepartment of Chemistry, Zhejiang University, Hangzhou 310027, People’s Republic of China
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 295 K
Mean(C–C) = 0.004 A˚ Disorder in main residue
Rfactor = 0.030
wRfactor = 0.079
Data-to-parameter ratio = 19.8
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
The Sn atom of the title compound, [Sn(C10H13)3(C6H4NO2)],
is four-coordinate and possesses a distorted tetrahedral geometry.
Comment
In several tris(2-methyl-2-phenylpropyl)tin carboxylates, such as tris(2-methyl-2-phenylpropyl)tin phenoxyacetate (Bao et al., 1998), acetate (Bomfimet al., 2002), arylcarboxylate with an organogermyl substituent (Fanget al., 2001) and bis[tris(2-methyl-2-phenylpropyl)tin(IV)] phthalate (Tian et al., 2005), the Sn atoms possess a tetrahedral geometry and do not associate into chain structuresviacarboxylate bridging, due to the effects of the bulky organic groups. In the title compound, (I), tetrahedral coordination is also observed (Fig. 1).
The Sn O2 separation of 3.032 (1) A˚ in (I) indicates that there is a weak interaction between these atoms, which distorts the tetrahedral geometry by opening up the C7—
Sn1—C27 angle to 119.94 (9) and reducing the O1—Sn1—
C17 angle to 93.64 (8). The bond dimensions around the Sn
atom in (I) (Table 1) are similar to those found in the carboxylate structures mentioned above.
There are no intermolecular Sn N interactions in the
crystal structure of (I); such interactions are found in
triphenyltin 3-pyridinecarboxylate (Ng et al., 1989),
tribenzyltin 3-pyridinecarboxylate (Yinet al., 2003) and tri(2-fluorobenzyl)tin 3-pyridinecarboxylate (Yinet al., 2004).
Experimental
acid (0.25 g, 2 mmol) in benzene (50 ml). Water was removed with a Dean–Stark trap and the condensation was complete in about 5 h. The resulting clear solution was evaporated under vacuum. The white solid obtained, (I), was recrystallized from ethanol and crystals of (I) were obtained from cyclohexane by slow evaporation at 298 K (yield 73.5%, m.p. 348–349 K). Analysis, found: C 67.62, H 6.66, N 2.17%; calculated for C36H43NO2Sn: C 67.51, H 6.77, N 2.19%. Spectroscopic
analysis: IR (KBr disc): as(COO) 1651, s(COO) 1339 cm1; 1H NMR (500 MHz, CDCl3,, p.p.m.): 9.10, 8.80, 8.21, 7.48 (4H,
pyri-dine-H), 7.30–7.12 (15H, m, 3 C6H5), 1.29 (6H, s, 3 CH2Sn), 1.24
(18H,s, 6 CH3);
119Sn NMR (111.9 MHz, CDCl
3,, p.p.m.): 104.7.
Crystal data
[Sn(C10H13)3(C6H4NO2)]
Mr= 640.40
Monoclinic,P21=n
a= 12.0660 (5) A˚ b= 18.2275 (8) A˚ c= 15.1284 (6) A˚
= 93.774 (1) V= 3320.0 (2) A˚3
Z= 4
Dx= 1.281 Mg m
3
MoKradiation Cell parameters from 7633
reflections
= 2.2–28.3 = 0.80 mm1
T= 295 (2) K Block, colourless 0.200.180.15 mm
Data collection
Bruker SMART APEX detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Bruker, 2002) Tmin= 0.856,Tmax= 0.889
37665 measured reflections
7571 independent reflections 6225 reflections withI> 2(I) Rint= 0.024
max= 27.5
h=15!15 k=23!23 l=19!19
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.030
wR(F2) = 0.080 S= 1.03 7571 reflections 383 parameters
H-atom parameters constrained
w= 1/[2
(Fo2) + (0.0439P)2
+ 0.4744P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.003
max= 0.34 e A˚
3
min=0.29 e A˚
[image:2.610.44.296.72.271.2]3
Table 1
Selected geometric parameters (A˚ ,).
Sn1—O1 2.0836 (15) Sn1—C17 2.141 (2)
Sn1—C27 2.142 (2) Sn1—C7 2.143 (2)
O1—Sn1—C17 93.64 (8) O1—Sn1—C27 104.72 (8) C17—Sn1—C27 115.80 (9)
O1—Sn1—C7 103.02 (9) C17—Sn1—C7 114.26 (9) C27—Sn1—C7 119.94 (9)
One phenyl group (C11–C16) is disordered over two positions;
ipsoatom C11 was refined with full occupancy, while the other atoms were refined in two parts, with site occupancy factors of 0.585 (8) (atoms C12–C16) and 0.415 (8) (atoms C120–C160). The phenyl rings
were restrained to be planar regular hexagons, with target C. . .C distances of 1.38 (1) A˚ . H atoms were placed in calculated positions and were included in the refinement in the riding-model approx-imation, with C—H = 0.93 A˚ andUiso(H) = 1.2Ueq(C) for aromatic H
atoms, C—H = 0.96 A˚ andUiso(H) = 1.5Ueq(C) for methyl H atoms,
and C—H = 0.97 A˚ andUiso(H) = 1.2Ueq(C) for methylene H atoms.
Data collection:SMART(Bruker, 2002); cell refinement:SAINT
(Bruker, 2002); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
ORTEP3 for Windows (Farrugia, 1997); software used to prepare material for publication:SHELXL97.
The authors thank the Natural Science Foundation of
Shandong Province and Qufu Normal University for
supporting this work.
References
Bao, M., He, Q.-L., Liu, B.-D., Xing, Y. & Liu, Y.-H. (1998).Chin. J. Inorg. Chem.14, 114–117.
Bomfim, J. A. S., Filgueiras, C. A. L., Howie, R. A., Low, J. N., Skakle, J. M. S., Wardell, J. L. & Wardell, S. M. S. V. (2002).Polyhedron,21, 1667–1676. Bruker (2002).SADABS,SAINTandSMART. Bruker AXS Inc., Madison,
Wisconsin, USA.
Fang, X., Song, X. & Xie, Q. (2001).J. Organomet. Chem.619, 43–48. Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Ng, S. W., Kumar Das, V. G., van Meurs, F., Schagen, J. D. & Straver, L. H. (1989).Acta Cryst.C45, 570–572.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Tian, L.-J., Sun, Y.-X., Yang, M. & Ng, S. W. (2005).Acta Cryst.E61, m74–m75. Yin, H. D., Wang, C., Ma, C. & Wang, D. (2004).J. Organomet. Chem.689, 246–
251.
Yin, H.-D., Wang, C.-H., Ma, C.-L., Wang, Y. & Fang, H.-X. (2003).Chin. J. Struct. Chem.22, 211–214.
metal-organic papers
Acta Cryst.(2005). E61, m1346–m1347 Tianet al. [Sn(C
10H13)3(C6H4NO2)]
m1347
Figure 1 [image:2.610.315.566.194.255.2]supporting information
Acta Cryst. (2005). E61, m1346–m1347 [https://doi.org/10.1107/S1600536805018635]
Tris(2-methyl-2-phenylpropyl)(pyridine-3-carboxylato)tin(IV)
Lai-Jin Tian, Yu-Xi Sun, Min Yang and Guo-Ming Yang
Tris(2-methyl-2-phenylpropyl)(pyridine-3-carboxylato)tin(IV)
Crystal data
[Sn(C10H13)3(C6H4NO2)]
Mr = 640.40 Monoclinic, P21/n
Hall symbol: -P 2yn a = 12.0660 (5) Å b = 18.2275 (8) Å c = 15.1284 (6) Å β = 93.774 (1)° V = 3320.0 (2) Å3
Z = 4
F(000) = 1328 Dx = 1.281 Mg m−3
Melting point = 348–349 K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 7633 reflections θ = 2.2–28.3°
µ = 0.80 mm−1
T = 295 K Block, colourless 0.20 × 0.18 × 0.15 mm
Data collection
Bruker SMART APEX detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2002) Tmin = 0.856, Tmax = 0.889
37665 measured reflections 7571 independent reflections 6225 reflections with I > 2σ(I) Rint = 0.024
θmax = 27.5°, θmin = 1.8°
h = −15→15 k = −23→23 l = −19→19
Refinement Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.030
wR(F2) = 0.080
S = 1.03 7571 reflections 383 parameters 162 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0439P)2 + 0.4744P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.003
Δρmax = 0.34 e Å−3
Δρmin = −0.29 e Å−3
Special details
supporting information
sup-2 Acta Cryst. (2005). E61, m1346–m1347
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2,
conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used
only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2
are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq Occ. (<1)
Sn1 0.787641 (11) 0.847036 (7) 0.754995 (9) 0.05053 (6)
O1 0.89808 (12) 0.92033 (9) 0.70210 (10) 0.0662 (4)
O2 0.99505 (18) 0.92400 (14) 0.83155 (13) 0.1019 (7)
N1 1.2029 (2) 1.08163 (19) 0.7312 (2) 0.1221 (11)
C1 0.9812 (2) 0.94108 (14) 0.75437 (17) 0.0669 (6)
C2 1.06145 (18) 0.99031 (12) 0.71198 (16) 0.0620 (5)
C3 1.0698 (2) 0.99300 (16) 0.62270 (18) 0.0815 (7)
H3 1.0241 0.9639 0.5853 0.098*
C4 1.1452 (3) 1.0384 (2) 0.5886 (2) 0.1047 (10)
H4 1.1527 1.0399 0.5278 0.126*
C5 1.2082 (3) 1.0808 (2) 0.6431 (3) 0.1201 (13)
H5 1.2592 1.1117 0.6184 0.144*
C6 1.1305 (2) 1.03498 (18) 0.7639 (2) 0.0916 (9)
H6 1.1267 1.0326 0.8251 0.110*
C7 0.8908 (2) 0.75451 (14) 0.79053 (16) 0.0752 (7)
H7A 0.9560 0.7724 0.8249 0.090*
H7B 0.8505 0.7233 0.8292 0.090*
C8 0.9305 (2) 0.70653 (14) 0.71524 (17) 0.0700 (6)
C9 1.0049 (3) 0.75288 (18) 0.6593 (3) 0.1139 (12)
H9A 1.0382 0.7221 0.6169 0.171*
H9B 1.0622 0.7755 0.6972 0.171*
H9C 0.9612 0.7902 0.6288 0.171*
C10 1.0009 (3) 0.64325 (19) 0.7580 (3) 0.1194 (13)
H10A 0.9568 0.6159 0.7970 0.179*
H10B 1.0645 0.6632 0.7911 0.179*
H10C 1.0250 0.6114 0.7125 0.179*
C11 0.8332 (2) 0.67291 (13) 0.66043 (18) 0.0731 (7)
C12 0.8173 (7) 0.6643 (5) 0.5707 (4) 0.1013 (17) 0.585 (8)
H12A 0.8711 0.6816 0.5346 0.122* 0.585 (8)
C13 0.7233 (7) 0.6303 (5) 0.5316 (5) 0.128 (3) 0.585 (8)
H13A 0.7136 0.6253 0.4704 0.154* 0.585 (8)
C14 0.6453 (6) 0.6046 (5) 0.5854 (6) 0.118 (3) 0.585 (8)
H14 0.5810 0.5832 0.5597 0.142* 0.585 (8)
C15 0.6587 (6) 0.6093 (5) 0.6764 (5) 0.109 (2) 0.585 (8)
H15 0.6056 0.5898 0.7117 0.131* 0.585 (8)
C16 0.7536 (8) 0.6439 (8) 0.7148 (5) 0.0916 (16) 0.585 (8)
H16 0.7641 0.6478 0.7761 0.110* 0.585 (8)
C12′ 0.8430 (9) 0.6835 (7) 0.5701 (5) 0.1013 (17) 0.415 (8)
H12′ 0.9044 0.7080 0.5505 0.122* 0.415 (8)
H13′ 0.7673 0.6643 0.4488 0.154* 0.415 (8)
C14′ 0.6699 (9) 0.6210 (7) 0.5378 (8) 0.118 (3) 0.415 (8)
H14′ 0.6161 0.6033 0.4964 0.142* 0.415 (8)
C15′ 0.6571 (9) 0.6102 (8) 0.6262 (8) 0.109 (2) 0.415 (8)
H15′ 0.5955 0.5856 0.6454 0.131* 0.415 (8)
C16′ 0.7393 (11) 0.6372 (11) 0.6862 (7) 0.0916 (16) 0.415 (8)
H16′ 0.7309 0.6309 0.7464 0.110* 0.415 (8)
C17 0.69022 (19) 0.83465 (13) 0.63242 (15) 0.0651 (6)
H17A 0.7397 0.8415 0.5851 0.078*
H17B 0.6650 0.7841 0.6292 0.078*
C18 0.5885 (2) 0.88352 (14) 0.61158 (16) 0.0687 (6)
C19 0.6246 (3) 0.96447 (16) 0.6202 (2) 0.1094 (11)
H19A 0.5629 0.9956 0.6026 0.164*
H19B 0.6843 0.9735 0.5826 0.164*
H19C 0.6491 0.9747 0.6805 0.164*
C20 0.5439 (3) 0.8691 (2) 0.5155 (2) 0.1112 (11)
H20A 0.5323 0.8174 0.5070 0.167*
H20B 0.5968 0.8863 0.4756 0.167*
H20C 0.4749 0.8946 0.5040 0.167*
C21 0.4952 (2) 0.86498 (15) 0.67090 (17) 0.0695 (6)
C22 0.4568 (2) 0.79432 (17) 0.67694 (18) 0.0858 (8)
H22 0.4921 0.7569 0.6478 0.103*
C23 0.3659 (4) 0.7773 (3) 0.7260 (3) 0.1260 (15)
H23 0.3398 0.7294 0.7287 0.151*
C24 0.3170 (4) 0.8316 (5) 0.7690 (3) 0.165 (3)
H24 0.2554 0.8206 0.8004 0.199*
C25 0.3530 (4) 0.9004 (4) 0.7684 (4) 0.157 (2)
H25 0.3200 0.9363 0.8015 0.188*
C26 0.4401 (3) 0.9177 (2) 0.7178 (3) 0.1125 (12)
H26 0.4629 0.9663 0.7150 0.135*
C27 0.7117 (2) 0.90815 (12) 0.85577 (14) 0.0633 (5)
H27A 0.7452 0.9565 0.8584 0.076*
H27B 0.6339 0.9146 0.8370 0.076*
C28 0.7183 (2) 0.87647 (14) 0.95056 (15) 0.0696 (6)
C29 0.6361 (3) 0.92004 (18) 1.0050 (2) 0.1109 (11)
H29A 0.5621 0.9142 0.9787 0.166*
H29B 0.6558 0.9711 1.0055 0.166*
H29C 0.6396 0.9018 1.0647 0.166*
C30 0.8359 (3) 0.88801 (19) 0.99237 (18) 0.0998 (10)
H30A 0.8390 0.8728 1.0532 0.150*
H30B 0.8552 0.9390 0.9892 0.150*
H30C 0.8874 0.8595 0.9609 0.150*
C31 0.68515 (18) 0.79585 (13) 0.94937 (13) 0.0612 (5)
C32 0.5939 (2) 0.77160 (15) 0.89743 (17) 0.0742 (6)
H32 0.5508 0.8052 0.8641 0.089*
C33 0.5658 (3) 0.69792 (17) 0.8943 (2) 0.0947 (9)
H33 0.5054 0.6825 0.8578 0.114*
supporting information
sup-4 Acta Cryst. (2005). E61, m1346–m1347
H34 0.6060 0.5987 0.9420 0.113*
C35 0.7129 (3) 0.67068 (18) 0.9960 (2) 0.0941 (9)
H35 0.7537 0.6368 1.0306 0.113*
C36 0.7431 (2) 0.74334 (16) 0.99882 (17) 0.0795 (7)
H36 0.8045 0.7575 1.0352 0.095*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Sn1 0.04881 (9) 0.05582 (10) 0.04646 (9) −0.00128 (5) −0.00061 (6) 0.00178 (6)
O1 0.0564 (8) 0.0746 (10) 0.0671 (10) −0.0149 (7) 0.0018 (7) 0.0026 (8)
O2 0.1006 (14) 0.1400 (18) 0.0641 (12) −0.0361 (13) −0.0022 (10) 0.0051 (12)
N1 0.0874 (19) 0.130 (3) 0.150 (3) −0.0480 (17) 0.0152 (19) −0.031 (2)
C1 0.0606 (13) 0.0769 (15) 0.0632 (15) −0.0070 (11) 0.0040 (11) −0.0080 (11)
C2 0.0487 (11) 0.0673 (13) 0.0704 (14) −0.0037 (9) 0.0061 (10) −0.0124 (11)
C3 0.0741 (16) 0.0931 (18) 0.0774 (17) −0.0221 (14) 0.0061 (13) −0.0083 (14)
C4 0.100 (2) 0.129 (3) 0.088 (2) −0.032 (2) 0.0293 (18) 0.0007 (19)
C5 0.087 (2) 0.131 (3) 0.146 (4) −0.042 (2) 0.038 (2) −0.004 (3)
C6 0.0708 (16) 0.115 (2) 0.090 (2) −0.0280 (16) 0.0124 (14) −0.0308 (17)
C7 0.0814 (16) 0.0823 (16) 0.0605 (14) 0.0242 (13) −0.0049 (12) 0.0067 (12)
C8 0.0608 (13) 0.0737 (15) 0.0768 (16) 0.0167 (11) 0.0137 (12) 0.0077 (12)
C9 0.088 (2) 0.102 (2) 0.159 (3) −0.0048 (17) 0.064 (2) −0.010 (2)
C10 0.109 (3) 0.115 (3) 0.131 (3) 0.061 (2) −0.011 (2) 0.006 (2)
C11 0.0766 (16) 0.0565 (12) 0.0867 (18) 0.0206 (11) 0.0090 (13) −0.0035 (12)
C12 0.105 (4) 0.100 (4) 0.097 (2) 0.015 (3) −0.003 (2) −0.037 (2)
C13 0.128 (5) 0.115 (5) 0.140 (5) 0.000 (4) 0.000 (4) −0.048 (4)
C14 0.122 (4) 0.094 (4) 0.137 (6) 0.019 (3) −0.009 (4) −0.030 (5)
C15 0.107 (3) 0.081 (2) 0.141 (6) −0.002 (2) 0.008 (4) −0.003 (5)
C16 0.073 (3) 0.070 (3) 0.132 (4) −0.0081 (19) 0.002 (3) −0.004 (4)
C12′ 0.105 (4) 0.100 (4) 0.097 (2) 0.015 (3) −0.003 (2) −0.037 (2)
C13′ 0.128 (5) 0.115 (5) 0.140 (5) 0.000 (4) 0.000 (4) −0.048 (4)
C14′ 0.122 (4) 0.094 (4) 0.137 (6) 0.019 (3) −0.009 (4) −0.030 (5)
C15′ 0.107 (3) 0.081 (2) 0.141 (6) −0.002 (2) 0.008 (4) −0.003 (5)
C16′ 0.073 (3) 0.070 (3) 0.132 (4) −0.0081 (19) 0.002 (3) −0.004 (4)
C17 0.0580 (13) 0.0796 (15) 0.0562 (13) 0.0030 (11) −0.0077 (10) −0.0081 (11)
C18 0.0645 (13) 0.0753 (15) 0.0644 (14) 0.0024 (11) −0.0100 (11) 0.0183 (12)
C19 0.113 (2) 0.0747 (18) 0.137 (3) −0.0047 (17) −0.012 (2) 0.0478 (19)
C20 0.090 (2) 0.178 (3) 0.0631 (18) −0.007 (2) −0.0190 (16) 0.034 (2)
C21 0.0569 (13) 0.0811 (16) 0.0679 (15) 0.0095 (11) −0.0156 (11) 0.0137 (12)
C22 0.0839 (18) 0.105 (2) 0.0655 (16) −0.0227 (16) −0.0208 (14) 0.0141 (14)
C23 0.109 (3) 0.180 (4) 0.084 (2) −0.064 (3) −0.029 (2) 0.029 (3)
C24 0.075 (3) 0.313 (9) 0.107 (4) −0.031 (4) −0.004 (2) −0.002 (5)
C25 0.083 (3) 0.221 (6) 0.168 (5) 0.042 (3) 0.020 (3) −0.024 (4)
C26 0.081 (2) 0.124 (3) 0.133 (3) 0.037 (2) 0.007 (2) 0.005 (2)
C27 0.0710 (13) 0.0605 (12) 0.0591 (13) −0.0019 (11) 0.0107 (10) −0.0034 (10)
C28 0.0813 (16) 0.0789 (15) 0.0494 (12) −0.0160 (13) 0.0104 (11) −0.0090 (11)
C29 0.155 (3) 0.099 (2) 0.085 (2) −0.015 (2) 0.053 (2) −0.0293 (17)
C31 0.0618 (12) 0.0832 (15) 0.0389 (10) −0.0080 (11) 0.0047 (9) 0.0021 (10)
C32 0.0708 (14) 0.0814 (16) 0.0679 (15) −0.0114 (12) −0.0141 (12) 0.0164 (12)
C33 0.098 (2) 0.094 (2) 0.089 (2) −0.0328 (17) −0.0226 (16) 0.0132 (16)
C34 0.109 (2) 0.0794 (19) 0.093 (2) −0.0168 (16) 0.0022 (19) 0.0210 (15)
C35 0.096 (2) 0.095 (2) 0.091 (2) 0.0030 (17) −0.0008 (18) 0.0342 (17)
C36 0.0688 (15) 0.105 (2) 0.0632 (15) −0.0075 (14) −0.0083 (12) 0.0159 (14)
Geometric parameters (Å, º)
Sn1—O1 2.0836 (15) C15′—H15′ 0.9300
Sn1—C17 2.141 (2) C16′—H16′ 0.9300
Sn1—C27 2.142 (2) C17—C18 1.533 (3)
Sn1—C7 2.143 (2) C17—H17A 0.9700
O1—C1 1.292 (3) C17—H17B 0.9700
O2—C1 1.209 (3) C18—C21 1.523 (4)
N1—C6 1.337 (4) C18—C20 1.538 (4)
N1—C5 1.339 (5) C18—C19 1.542 (4)
C1—C2 1.495 (3) C19—H19A 0.9600
C2—C3 1.362 (3) C19—H19B 0.9600
C2—C6 1.375 (3) C19—H19C 0.9600
C3—C4 1.357 (4) C20—H20A 0.9600
C3—H3 0.9300 C20—H20B 0.9600
C4—C5 1.332 (5) C20—H20C 0.9600
C4—H4 0.9300 C21—C22 1.374 (4)
C5—H5 0.9300 C21—C26 1.389 (4)
C6—H6 0.9300 C22—C23 1.399 (5)
C7—C8 1.537 (3) C22—H22 0.9300
C7—H7A 0.9700 C23—C24 1.342 (7)
C7—H7B 0.9700 C23—H23 0.9300
C8—C11 1.521 (4) C24—C25 1.328 (8)
C8—C9 1.528 (4) C24—H24 0.9300
C8—C10 1.549 (4) C25—C26 1.376 (6)
C9—H9A 0.9600 C25—H25 0.9300
C9—H9B 0.9600 C26—H26 0.9300
C9—H9C 0.9600 C27—C28 1.543 (3)
C10—H10A 0.9600 C27—H27A 0.9700
C10—H10B 0.9600 C27—H27B 0.9700
C10—H10C 0.9600 C28—C31 1.523 (3)
C11—C12 1.368 (6) C28—C30 1.530 (4)
C11—C16′ 1.386 (7) C28—C29 1.549 (4)
C11—C12′ 1.392 (7) C29—H29A 0.9600
C11—C16 1.408 (6) C29—H29B 0.9600
C12—C13 1.389 (7) C29—H29C 0.9600
C12—H12A 0.9300 C30—H30A 0.9600
C13—C14 1.367 (7) C30—H30B 0.9600
C13—H13A 0.9300 C30—H30C 0.9600
C14—C15 1.379 (6) C31—C36 1.377 (3)
supporting information
sup-6 Acta Cryst. (2005). E61, m1346–m1347
C15—C16 1.401 (6) C32—C33 1.385 (4)
C15—H15 0.9300 C32—H32 0.9300
C16—H16 0.9300 C33—C34 1.355 (4)
C12′—C13′ 1.396 (7) C33—H33 0.9300
C12′—H12′ 0.9300 C34—C35 1.338 (5)
C13′—C14′ 1.374 (7) C34—H34 0.9300
C13′—H13′ 0.9300 C35—C36 1.373 (4)
C14′—C15′ 1.370 (7) C35—H35 0.9300
C14′—H14′ 0.9300 C36—H36 0.9300
C15′—C16′ 1.389 (7)
O1—Sn1—C17 93.64 (8) C11—C16′—H16′ 118.5
O1—Sn1—C27 104.72 (8) C15′—C16′—H16′ 118.5
C17—Sn1—C27 115.80 (9) C18—C17—Sn1 120.24 (16)
O1—Sn1—C7 103.02 (9) C18—C17—H17A 107.3
C17—Sn1—C7 114.26 (9) Sn1—C17—H17A 107.3
C27—Sn1—C7 119.94 (9) C18—C17—H17B 107.3
C1—O1—Sn1 116.28 (15) Sn1—C17—H17B 107.3
C6—N1—C5 115.9 (3) H17A—C17—H17B 106.9
O2—C1—O1 124.6 (2) C21—C18—C17 111.26 (19)
O2—C1—C2 121.1 (2) C21—C18—C20 107.0 (2)
O1—C1—C2 114.3 (2) C17—C18—C20 108.7 (2)
C3—C2—C6 117.7 (2) C21—C18—C19 112.3 (2)
C3—C2—C1 122.6 (2) C17—C18—C19 108.7 (2)
C6—C2—C1 119.7 (2) C20—C18—C19 108.8 (2)
C4—C3—C2 119.6 (3) C18—C19—H19A 109.5
C4—C3—H3 120.2 C18—C19—H19B 109.5
C2—C3—H3 120.2 H19A—C19—H19B 109.5
C5—C4—C3 119.2 (3) C18—C19—H19C 109.5
C5—C4—H4 120.4 H19A—C19—H19C 109.5
C3—C4—H4 120.4 H19B—C19—H19C 109.5
C4—C5—N1 124.1 (3) C18—C20—H20A 109.5
C4—C5—H5 117.9 C18—C20—H20B 109.5
N1—C5—H5 117.9 H20A—C20—H20B 109.5
N1—C6—C2 123.5 (3) C18—C20—H20C 109.5
N1—C6—H6 118.3 H20A—C20—H20C 109.5
C2—C6—H6 118.3 H20B—C20—H20C 109.5
C8—C7—Sn1 117.77 (16) C22—C21—C26 116.1 (3)
C8—C7—H7A 107.9 C22—C21—C18 120.8 (3)
Sn1—C7—H7A 107.9 C26—C21—C18 123.0 (3)
C8—C7—H7B 107.9 C21—C22—C23 121.5 (4)
Sn1—C7—H7B 107.9 C21—C22—H22 119.2
H7A—C7—H7B 107.2 C23—C22—H22 119.2
C11—C8—C9 112.4 (2) C24—C23—C22 118.6 (5)
C11—C8—C7 111.48 (19) C24—C23—H23 120.7
C9—C8—C7 108.6 (2) C22—C23—H23 120.7
C11—C8—C10 108.1 (2) C25—C24—C23 122.6 (5)
C7—C8—C10 107.6 (2) C23—C24—H24 118.7
C8—C9—H9A 109.5 C24—C25—C26 118.8 (5)
C8—C9—H9B 109.5 C24—C25—H25 120.6
H9A—C9—H9B 109.5 C26—C25—H25 120.6
C8—C9—H9C 109.5 C25—C26—C21 122.3 (4)
H9A—C9—H9C 109.5 C25—C26—H26 118.8
H9B—C9—H9C 109.5 C21—C26—H26 118.8
C8—C10—H10A 109.5 C28—C27—Sn1 117.95 (16)
C8—C10—H10B 109.5 C28—C27—H27A 107.8
H10A—C10—H10B 109.5 Sn1—C27—H27A 107.8
C8—C10—H10C 109.5 C28—C27—H27B 107.8
H10A—C10—H10C 109.5 Sn1—C27—H27B 107.8
H10B—C10—H10C 109.5 H27A—C27—H27B 107.2
C12—C11—C16′ 99.3 (5) C31—C28—C30 111.9 (2)
C16′—C11—C12′ 117.7 (5) C31—C28—C27 110.66 (18)
C12—C11—C16 118.7 (4) C30—C28—C27 108.8 (2)
C12′—C11—C16 136.9 (5) C31—C28—C29 108.9 (2)
C12—C11—C8 129.8 (4) C30—C28—C29 108.6 (2)
C16′—C11—C8 130.7 (5) C27—C28—C29 107.9 (2)
C12′—C11—C8 111.5 (4) C28—C29—H29A 109.5
C16—C11—C8 111.3 (3) C28—C29—H29B 109.5
C11—C12—C13 122.0 (5) H29A—C29—H29B 109.5
C11—C12—H12A 119.0 C28—C29—H29C 109.5
C13—C12—H12A 119.0 H29A—C29—H29C 109.5
C14—C13—C12 118.3 (6) H29B—C29—H29C 109.5
C14—C13—H13A 120.8 C28—C30—H30A 109.5
C12—C13—H13A 120.8 C28—C30—H30B 109.5
C13—C14—C15 122.2 (6) H30A—C30—H30B 109.5
C13—C14—H14 118.9 C28—C30—H30C 109.5
C15—C14—H14 118.9 H30A—C30—H30C 109.5
C14—C15—C16 118.8 (6) H30B—C30—H30C 109.5
C14—C15—H15 120.6 C36—C31—C32 116.3 (2)
C16—C15—H15 120.6 C36—C31—C28 122.7 (2)
C15—C16—C11 119.8 (5) C32—C31—C28 120.9 (2)
C15—C16—H16 120.1 C31—C32—C33 120.9 (3)
C11—C16—H16 120.1 C31—C32—H32 119.6
C11—C12′—C13′ 120.0 (7) C33—C32—H32 119.6
C11—C12′—H12′ 120.0 C34—C33—C32 120.8 (3)
C13′—C12′—H12′ 120.0 C34—C33—H33 119.6
C14′—C13′—C12′ 120.2 (7) C32—C33—H33 119.6
C14′—C13′—H13′ 119.9 C35—C34—C33 119.3 (3)
C12′—C13′—H13′ 119.9 C35—C34—H34 120.4
C15′—C14′—C13′ 121.4 (7) C33—C34—H34 120.4
C15′—C14′—H14′ 119.3 C34—C35—C36 120.8 (3)
C13′—C14′—H14′ 119.3 C34—C35—H35 119.6
C14′—C15′—C16′ 117.7 (7) C36—C35—H35 119.6
C14′—C15′—H15′ 121.1 C35—C36—C31 122.0 (3)
supporting information
sup-8 Acta Cryst. (2005). E61, m1346–m1347
C11—C16′—C15′ 123.0 (7) C31—C36—H36 119.0
C17—Sn1—O1—C1 −175.87 (17) C8—C11—C12′—C13′ −179.2 (7)
C27—Sn1—O1—C1 66.25 (18) C11—C12′—C13′—C14′ 0.0 (14)
C7—Sn1—O1—C1 −59.94 (18) C12′—C13′—C14′—C15′ 1 (2)
Sn1—O1—C1—O2 −4.1 (3) C13′—C14′—C15′—C16′ 0 (2)
Sn1—O1—C1—C2 176.76 (14) C12—C11—C16′—C15′ −5 (2)
O2—C1—C2—C3 159.1 (3) C12′—C11—C16′—C15′ 2 (2)
O1—C1—C2—C3 −21.7 (3) C16—C11—C16′—C15′ 174 (6)
O2—C1—C2—C6 −20.7 (4) C8—C11—C16′—C15′ 179.3 (12)
O1—C1—C2—C6 158.5 (2) C14′—C15′—C16′—C11 −1 (3)
C6—C2—C3—C4 0.5 (4) O1—Sn1—C17—C18 −92.67 (19)
C1—C2—C3—C4 −179.3 (3) C27—Sn1—C17—C18 15.6 (2)
C2—C3—C4—C5 −1.4 (5) C7—Sn1—C17—C18 161.29 (18)
C3—C4—C5—N1 0.3 (7) Sn1—C17—C18—C21 −69.3 (2)
C6—N1—C5—C4 1.6 (7) Sn1—C17—C18—C20 173.1 (2)
C5—N1—C6—C2 −2.6 (5) Sn1—C17—C18—C19 54.8 (3)
C3—C2—C6—N1 1.6 (4) C17—C18—C21—C22 −53.5 (3)
C1—C2—C6—N1 −178.6 (3) C20—C18—C21—C22 65.1 (3)
O1—Sn1—C7—C8 −72.2 (2) C19—C18—C21—C22 −175.6 (2)
C17—Sn1—C7—C8 27.9 (2) C17—C18—C21—C26 130.1 (3)
C27—Sn1—C7—C8 172.04 (18) C20—C18—C21—C26 −111.4 (3)
Sn1—C7—C8—C11 −60.5 (3) C19—C18—C21—C26 8.0 (4)
Sn1—C7—C8—C9 63.9 (3) C26—C21—C22—C23 1.5 (4)
Sn1—C7—C8—C10 −178.9 (2) C18—C21—C22—C23 −175.2 (2)
C9—C8—C11—C12 16.4 (6) C21—C22—C23—C24 −1.2 (5)
C7—C8—C11—C12 138.6 (5) C22—C23—C24—C25 −1.5 (8)
C10—C8—C11—C12 −103.3 (6) C23—C24—C25—C26 3.6 (9)
C9—C8—C11—C16′ −169.3 (13) C24—C25—C26—C21 −3.3 (7)
C7—C8—C11—C16′ −47.1 (13) C22—C21—C26—C25 0.8 (5)
C10—C8—C11—C16′ 71.0 (13) C18—C21—C26—C25 177.3 (3)
C9—C8—C11—C12′ 8.5 (6) O1—Sn1—C27—C28 −124.41 (17)
C7—C8—C11—C12′ 130.7 (6) C17—Sn1—C27—C28 134.06 (17)
C10—C8—C11—C12′ −111.2 (6) C7—Sn1—C27—C28 −9.6 (2)
C9—C8—C11—C16 −167.4 (7) Sn1—C27—C28—C31 −48.2 (2)
C7—C8—C11—C16 −45.2 (7) Sn1—C27—C28—C30 75.2 (3)
C10—C8—C11—C16 72.9 (7) Sn1—C27—C28—C29 −167.22 (18)
C16′—C11—C12—C13 2.8 (13) C30—C28—C31—C36 14.6 (3)
C12′—C11—C12—C13 −159 (3) C27—C28—C31—C36 136.1 (2)
C16—C11—C12—C13 2.5 (11) C29—C28—C31—C36 −105.4 (3)
C8—C11—C12—C13 178.4 (5) C30—C28—C31—C32 −165.3 (2)
C11—C12—C13—C14 −0.5 (11) C27—C28—C31—C32 −43.7 (3)
C12—C13—C14—C15 −2.0 (13) C29—C28—C31—C32 74.7 (3)
C13—C14—C15—C16 2.3 (15) C36—C31—C32—C33 −1.9 (4)
C14—C15—C16—C11 −0.2 (17) C28—C31—C32—C33 178.0 (3)
C12—C11—C16—C15 −2.1 (15) C31—C32—C33—C34 1.8 (5)
C16′—C11—C16—C15 −3 (4) C32—C33—C34—C35 −0.5 (6)
C8—C11—C16—C15 −178.8 (10) C34—C35—C36—C31 0.5 (5)
C12—C11—C12′—C13′ 19 (2) C32—C31—C36—C35 0.8 (4)
C16′—C11—C12′—C13′ −1.1 (14) C28—C31—C36—C35 −179.1 (3)
