metal-organic papers
Acta Cryst.(2006). E62, m7–m9 doi:10.1107/S1600536805039541 Tianet al. [Sn(C
6H11)3(C8H6NO5)]
m7
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Tricyclohexyl(4-nitrophenoxyacetato)tin(IV)
Lai-Jin Tian,* Hai-Xia Yu, Yu-Xi Sun and Feng-Yang Yu
Department of Chemistry, Qufu Normal University, Qufu 273165, Shandong, People’s Republic of China
Correspondence e-mail: laijintian@163.com
Key indicators
Single-crystal X-ray study T= 295 K
Mean(C–C) = 0.005 A˚ Rfactor = 0.032 wRfactor = 0.076
Data-to-parameter ratio = 18.1
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2006 International Union of Crystallography Printed in Great Britain – all rights reserved
The coordination geometry about the Sn atom in the title compound, [Sn(C6H11)3(C8H6NO5)], is best described as
highly distorted tetrahedral. There is an intermolecular interaction, 2.769 (2) A˚ , between the Sn atom and the carbonyl O atom of the carboxylate group of an adjacent molecule.
Comment
Tricyclohexyltin carboxylates, (C6H11)3Sn(O2CR), generally
have a tetrahedral structure and do not auto-associate into chain structuresviacarboxylate bridging, due to the effects of the three bulky organic groups at Sn (Chandrasekhar et al., 2002; Tiekink, 1991, 1994). 4-Nitrophenoxyacetic acid, whose crystal structure has been reported previously (Kumar & Rao, 1980), is a pesticide intermediate used in the synthesis of fungicides and plant-growth regulators (Xue & Zou, 1999). We present here the crystal structure analysis of its tricyclo-hexyltin ester, (I).
In (I), the Sn atom is best described as having a highly distorted tetrahedral geometry, the range of angles subtended at Sn being 89.83 (9)–124.93 (11) (Fig. 1, Table 1). An
Sn1 O2i intermolecular contact of 2.769 (2) A˚ [symmetry code: (i) x + 2, y + 1
2, z + 1
2] is not considered to be a
significant bonding interaction (Willem et al., 1998). If the Sn1 O2iinteraction were considered as a significant bonding interaction, then (I) would be described as a five-coordinate complex with the Sn atom having a trans-R3SnO2 trigonal–
bipyramidal geometry. In that case, atoms C9, C15 and C21 would define the trigonal plane and a one-dimensional polymer would be formed through the apical positions occu-pied by O1 and O2 (Fig. 2). However, in this description, the Sn atom would lie 0.238 (2) A˚ out of the trigonal plane.
Atom O2iexerts a steric influence on atom Sn1 from the opposite side of atom O1, and thus contributes to the
tion of the tetrahedral geometry around the Sn atom, by opening up the C—Sn1—C angles and contracting the O1— Sn1—C angles. The Sn1 O2 separation of 3.523 (3) A˚ , and the Sn1—O1 distance of 2.1317 (19) A˚ , are longer than those found in previously reported tricyclohexyltin carboxylates, such as tricyclohexyltin indole-3-acetate (Molloyet al., 1986), trifluoroacetate (Calogero et al., 1980), N-phthaloylglycinate (Ng & Kumar Das, 1997a), (N,N -diethylthiocarbamoyl-thio)acetate (Ng & Kumar Das, 1997b), 2-[2-(2-hydroxy-5-methylphenyl)-1-diazenyl]benzoate (Willemet al., 1998), 2-(4-chlorophenyl)-3-methylbutyrate (Song et al., 2003) and 4-biphenylacetate (Tianet al., 2005). However, the three Sn—C distances in (I) are similar to those of the carboxylate struc-tures mentioned above (Table 1).
Experimental
Tricyclohexyltin hydroxide (0.577 g, 1.5 mmol) and
4-nitrophenoxy-with azeotropic removal of water via a Dean–Stark trap. The resulting clear solution was evaporated to dryness under a vacuum. The pale-yellow solid obtained, (I), was recrystallized from ethanol and crystals of (I) were obtained from hexane–chloroform (1:1) by slow evaporation at 298 K (yield 70.3%; m.p. 358–359 K). Analysis, found: C 55.22, H 6.69, N 2.37%; calculated for C26H39NO5Sn: C 55.34, H 6.97, N 2.48%.
Crystal data
[Sn(C6H11)3(C8H6NO5)]
Mr= 564.27
Monoclinic,P21=c a= 10.8892 (15) A˚
b= 11.7837 (16) A˚
c= 20.768 (3) A˚ = 101.456 (2) V= 2611.8 (6) A˚3
Z= 4
Dx= 1.435 Mg m
3
MoKradiation Cell parameters from 5699
reflections = 2.5–27.6
= 1.01 mm1
T= 295 (2) K Prism, pale yellow 0.220.090.09 mm
Data collection
Bruker SMART APEX area-detector diffractometer ’and!scans
Absorption correction: multi-scan (SADABS; Bruker, 2002)
Tmin= 0.808,Tmax= 0.914
20503 measured reflections
5390 independent reflections 4395 reflections withI> 2(I)
Rint= 0.040
max= 26.5
h=13!13
k=14!14
l=26!25
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.032
wR(F2) = 0.076
S= 1.02 5390 reflections 298 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.037P)2
+ 0.0495P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 0.50 e A˚
3
min=0.41 e A˚
[image:2.610.46.297.71.252.2]3
Table 1
Selected geometric parameters (A˚ ,).
Sn1—O1 2.1317 (19)
Sn1—C21 2.144 (2)
Sn1—C9 2.152 (3)
Sn1—C15 2.155 (3)
Sn1—O2i
2.769 (2)
O1—C1 1.274 (3)
O2—C1 1.217 (3)
O1—Sn1—C21 89.83 (9) O1—Sn1—C9 99.86 (9) C21—Sn1—C9 116.16 (10) O1—Sn1—C15 98.68 (9) C21—Sn1—C15 115.26 (11)
C9—Sn1—C15 124.93 (11) O1—Sn1—O2i 170.61 (11) C21—Sn1—O2i
81.49 (9) C9—Sn1—O2i
87.27 (9) C15—Sn1—O2i 81.95 (9) Symmetry code: (i)xþ2;yþ1
2;zþ 1 2.
H atoms were placed in calculated positions and refined in the riding-model approximation, with Uiso(H) = 1.2Ueq(carrier C). Constrained C—H distances were 0.93 for aromatic CH, 0.97 for methylene CH2and 0.98 A˚ for methine CH.
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: ORTEP-3 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
Figure 1
The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
Figure 2
[image:2.610.46.295.313.472.2]References
Bruker (2002).SADABS,SAINTandSMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Calogero, S., Ganis, P., Peruzzo, V. & Tagliavini, G. (1980). J. Organomet. Chem.191, 381–390.
Chandrasekhar, V., Nagendran, S. & Baskar, V. (2002).Coord. Chem. Rev.235, 1–52.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Kumar, S. V. & Rao, L. M. (1980).Acta Cryst.B36, 1218–1220.
Molloy, K. C., Purcell, T. G., Hahn, E., Schumann H. & Zuckermann, J. J. (1986).Organometallics,5, 85–89.
Ng, S. W. & Kumar Das, V. G. (1997a).Acta Cryst.C53, 546–548. Ng, S. W. & Kumar Das, V. G. (1997b).Acta Cryst.C53, 548–549.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Song, X., Cahill, C. & Eng, G. (2003).Appl. Organomet. Chem. 17, 743– 744.
Tian, L.-J., Sun, Y.-X, Gao, Y.-Z. & Yang, G.-M. (2005).Acta Cryst.E61, m1199–m1200.
Tiekink, E. R. T. (1991).Appl. Organomet. Chem.5, 1–23. Tiekink, E. R. T. (1994).Trends Organomet. Chem.1, 71–116.
Willem, R., Verbruggen, I., Gielen, M., Biesemans, M., Mahieu, B., Basu Baul, T. S. & Tiekink, E. R. T. (1998).Organometallics,17, 5758–5766. Xue, S. & Zou, J. (1999).Chin. J. Pestic. Sci.1, 85–87.
metal-organic papers
Acta Cryst.(2006). E62, m7–m9 Tianet al. [Sn(C
supporting information
Acta Cryst. (2006). E62, m7–m9 [doi:10.1107/S1600536805039541]
Tricyclohexyl(4-nitrophenoxyacetato)tin(IV)
Lai-Jin Tian, Hai-Xia Yu, Yu-Xi Sun and Feng-Yang Yu
S1. Comment
Tricyclohexyltin carboxylates, (C6H11)3Sn(O2CR), generally have a tetrahedral structure and do not auto-associate into
chain structures via carboxylate bridging, due to the effects of the three bulky organic groups at Sn (Chandrasekhar et al.,
2002; Tiekink, 1991, 1994). 4-Nitrophenoxyacetic acid, whose crystal structure has been reported previously (Kumar &
Rao, 1980), is a pesticide intermediate used in the synthesis of fungicides and plant-growth regulators (Xue & Zou,
1999). We present here the crystal structure analysis of its tricyclohexyltin ester, (I).
In (I), the Sn atom is best described as having a highly distorted tetrahedral geometry, with the range of angles
subtended at Sn being 89.83 (9)–124.93 (11)° (Fig. 1, Table 1). An Sn1···O2i intermolecular contact of 2.769 (2) Å
[symmetry code: (i) −x + 2, y + 1/2, −z + 1/2] is not considered to be a significant bonding interaction (Willem et al.,
1998). If the Sn1···O2i interaction were considered as a significant bonding interaction, then (I) would be described as a
five-coordinate complex with the Sn atom having a trans-R3SnO2 trigonal–bipyramidal geometry. In that case, atoms C9,
C15 and C21 would define the trigonal plane and a one-dimensional polymer would be formed through the apical
positions occupied by O1 and O2 (Fig. 2). However, in this description, the Sn atom would lie 0.238 (2) Å out of the
trigonal plane.
Atom O2i exerts a steric influence on atom Sn1 from the opposite of atom O1, and thus contributes to the distortion of
the tetrahedral geometry around the Sn atom, by opening up the C—Sn1—C angles and contracting the O1—Sn1—C
angles. The Sn1···O2 separation of 3.523 (3) Å, and the Sn1—O1 distance of 2.1317 (19) Å, are longer than those found
in previously reported tricyclohexyltin carboxylates, such as tricyclohexyltin indole-3-acetate (Molloy et al., 1986),
tri-fluoroacetate (Calogero et al., 1980), N-phthaloylglycinate (Ng & Kumar Das, 1997a), (N,N
-diethylthiocarbamoylthio)-acetate (Ng & Kumar Das, 1997b), 2-[2-(2-hydroxy-5-methylphenyl)-1-diazenyl]benzoate (Willem et al., 1998),
2-(4-chlorophenyl)-3-methylbutyrate (Song et al., 2003) and 4-biphenylacetate (Tian et al., 2005). However, the three Sn—C
distances in (I) are similar to those of the carboxylate structures mentioned above (Table 1).
S2. Experimental
Tricyclohexyltin hydroxide (0.577 g, 1.5 mmol) and 4-nitrophenoxyacetic acid (0.30 g, 1.5 mmol) in toluene (60 ml)
were refluxed for 4 h with azeotropic removal of water via a Dean–Stark trap. The resulting clear solution was rotary
evaporated under vacuum. The pale-yellow solid obtained, (I), was recrystallized from ethanol and crystals of (I) were
obtained from hexane–chloroform (1:1) by slow evaporation at 298 K (yield 70.3%; m.p. 358–359 K). Analysis, found: C
55.22, H 6.69, N 2.37%; calculated for C26H39NO5Sn: C 55.34, H 6.97, N 2.48%.
S3. Refinement
H atoms were placed in calculated positions and refined in the riding-model approximation, with Uiso(H) = 1.2Ueq(carrier
supporting information
[image:5.610.133.484.72.334.2]sup-2
Acta Cryst. (2006). E62, m7–m9Figure 1
The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability
level. H atoms have been omitted for clarity.
Figure 2
[image:5.610.131.485.386.607.2]Tricyclohexyl(4-nitrophenoxyacetato)tin(IV)
Crystal data
[Sn(C6H11)3(C8H6NO5)]
Mr = 564.27 Monoclinic, P21/c Hall symbol: -P 2ybc
a = 10.8892 (15) Å
b = 11.7837 (16) Å
c = 20.768 (3) Å
β = 101.456 (2)°
V = 2611.8 (6) Å3
Z = 4
F(000) = 1168
Dx = 1.435 Mg m−3
Melting point = 358–359 K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 5699 reflections
θ = 2.5–27.6°
µ = 1.01 mm−1
T = 295 K
Prism, pale-yellow 0.22 × 0.09 × 0.09 mm
Data collection
Bruker SMART APEX area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
Tmin = 0.808, Tmax = 0.914
20503 measured reflections 5390 independent reflections 4395 reflections with I > 2σ(I)
Rint = 0.040
θmax = 26.5°, θmin = 1.9°
h = −13→13
k = −14→14
l = −26→25
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.032
wR(F2) = 0.076
S = 1.02 5390 reflections 298 parameters 0 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) + (0.037P)2 + 0.0495P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001 Δρmax = 0.50 e Å−3 Δρmin = −0.41 e Å−3
Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
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
Sn1 0.951222 (15) 0.883451 (15) 0.225197 (8) 0.03471 (8)
N1 0.2815 (3) 0.5962 (2) 0.05501 (19) 0.0701 (9)
O1 0.89188 (18) 0.74291 (15) 0.16204 (10) 0.0483 (5)
supporting information
sup-4
Acta Cryst. (2006). E62, m7–m9O3 0.7902 (2) 0.63325 (18) 0.05222 (10) 0.0571 (6)
O4 0.2495 (3) 0.5532 (3) 0.10184 (17) 0.0992 (10)
O5 0.2095 (3) 0.6298 (2) 0.00551 (17) 0.0986 (10)
C1 0.9230 (3) 0.6386 (2) 0.16429 (14) 0.0395 (6)
C2 0.8826 (3) 0.5762 (3) 0.09964 (14) 0.0519 (8)
H2A 0.9559 0.5633 0.0807 0.062*
H2B 0.8498 0.5025 0.1086 0.062*
C3 0.6687 (3) 0.6261 (2) 0.05845 (14) 0.0470 (7)
C4 0.5810 (3) 0.6657 (3) 0.00457 (15) 0.0585 (9)
H4 0.6082 0.6978 −0.0310 0.070*
C5 0.4557 (3) 0.6573 (3) 0.00405 (17) 0.0599 (9)
H5A 0.3976 0.6840 −0.0317 0.072*
C6 0.4160 (3) 0.6097 (2) 0.05625 (17) 0.0538 (8)
C7 0.5007 (3) 0.5729 (3) 0.11058 (16) 0.0556 (8)
H7 0.4724 0.5421 0.1462 0.067*
C8 0.6273 (3) 0.5818 (3) 0.11194 (14) 0.0494 (7)
H8 0.6848 0.5581 0.1488 0.059*
C9 0.8754 (2) 0.8342 (2) 0.30918 (13) 0.0399 (6)
H9 0.8450 0.9035 0.3269 0.048*
C10 0.7627 (3) 0.7557 (3) 0.28923 (17) 0.0599 (9)
H10A 0.7016 0.7917 0.2549 0.072*
H10B 0.7895 0.6857 0.2716 0.072*
C11 0.7021 (3) 0.7286 (3) 0.34714 (19) 0.0730 (11)
H11A 0.6341 0.6752 0.3335 0.088*
H11B 0.6671 0.7974 0.3618 0.088*
C12 0.7966 (3) 0.6782 (3) 0.40366 (17) 0.0656 (10)
H12A 0.7569 0.6674 0.4411 0.079*
H12B 0.8230 0.6045 0.3908 0.079*
C13 0.9098 (3) 0.7532 (3) 0.42346 (15) 0.0608 (9)
H13A 0.9706 0.7155 0.4572 0.073*
H13B 0.8853 0.8234 0.4418 0.073*
C14 0.9697 (3) 0.7799 (3) 0.36470 (14) 0.0457 (7)
H14A 1.0399 0.8310 0.3783 0.055*
H14B 1.0015 0.7104 0.3490 0.055*
C15 1.1474 (3) 0.8819 (2) 0.22108 (15) 0.0435 (7)
H15 1.1735 0.9617 0.2230 0.052*
C16 1.1720 (3) 0.8362 (3) 0.15582 (16) 0.0597 (9)
H16A 1.1471 0.7571 0.1511 0.072*
H16B 1.1219 0.8783 0.1198 0.072*
C17 1.3102 (3) 0.8470 (3) 0.15274 (19) 0.0684 (10)
H17A 1.3240 0.8136 0.1121 0.082*
H17B 1.3323 0.9267 0.1525 0.082*
C18 1.3922 (3) 0.7906 (4) 0.20863 (19) 0.0757 (11)
H18A 1.4791 0.8036 0.2061 0.091*
H18B 1.3771 0.7094 0.2061 0.091*
C19 1.3688 (3) 0.8347 (4) 0.27340 (19) 0.0840 (12)
H19A 1.3943 0.9136 0.2784 0.101*
C20 1.2314 (3) 0.8249 (3) 0.27766 (16) 0.0608 (9)
H20A 1.2089 0.7453 0.2783 0.073*
H20B 1.2189 0.8589 0.3184 0.073*
C21 0.8370 (2) 0.9942 (2) 0.15620 (12) 0.0369 (6)
H21 0.8544 1.0720 0.1722 0.044*
C22 0.6970 (3) 0.9733 (3) 0.15166 (15) 0.0532 (8)
H22A 0.6778 0.8949 0.1394 0.064*
H22B 0.6761 0.9859 0.1944 0.064*
C23 0.6175 (3) 1.0515 (3) 0.10124 (16) 0.0617 (9)
H23A 0.5297 1.0325 0.0975 0.074*
H23B 0.6292 1.1295 0.1162 0.074*
C24 0.6527 (3) 1.0407 (3) 0.03479 (15) 0.0599 (9)
H24A 0.6337 0.9645 0.0181 0.072*
H24B 0.6031 1.0934 0.0044 0.072*
C25 0.7895 (3) 1.0647 (3) 0.03856 (15) 0.0576 (8)
H25A 0.8069 1.1433 0.0511 0.069*
H25B 0.8100 1.0535 −0.0044 0.069*
C26 0.8703 (3) 0.9875 (2) 0.08817 (13) 0.0471 (7)
H26A 0.9576 1.0082 0.0916 0.056*
H26B 0.8602 0.9098 0.0725 0.056*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Sn1 0.02916 (11) 0.03885 (12) 0.03603 (12) 0.00299 (8) 0.00626 (8) 0.00653 (8)
N1 0.063 (2) 0.0443 (17) 0.095 (3) −0.0010 (14) −0.0023 (19) −0.0102 (16)
O1 0.0547 (13) 0.0347 (11) 0.0534 (13) −0.0010 (9) 0.0057 (10) −0.0028 (9)
O2 0.0559 (13) 0.0508 (12) 0.0487 (13) 0.0055 (10) 0.0049 (10) 0.0068 (10)
O3 0.0655 (15) 0.0666 (15) 0.0387 (12) 0.0008 (11) 0.0092 (11) 0.0010 (10)
O4 0.0727 (19) 0.096 (2) 0.129 (3) −0.0126 (17) 0.0192 (19) 0.021 (2)
O5 0.0691 (18) 0.091 (2) 0.118 (3) 0.0074 (15) −0.0260 (18) −0.0011 (17)
C1 0.0360 (15) 0.0408 (17) 0.0440 (16) −0.0038 (12) 0.0132 (13) 0.0000 (13)
C2 0.060 (2) 0.0463 (17) 0.0498 (19) 0.0051 (15) 0.0118 (15) −0.0067 (15)
C3 0.062 (2) 0.0372 (16) 0.0406 (16) −0.0015 (14) 0.0071 (15) −0.0070 (13)
C4 0.079 (3) 0.0522 (19) 0.0411 (18) 0.0051 (18) 0.0046 (17) 0.0088 (15)
C5 0.068 (2) 0.0491 (18) 0.054 (2) 0.0077 (17) −0.0088 (17) −0.0004 (16)
C6 0.057 (2) 0.0380 (17) 0.061 (2) 0.0030 (14) −0.0009 (16) −0.0098 (15)
C7 0.066 (2) 0.0508 (18) 0.0496 (19) −0.0001 (16) 0.0095 (16) 0.0028 (15)
C8 0.054 (2) 0.0527 (18) 0.0388 (17) 0.0038 (15) 0.0026 (14) 0.0028 (14)
C9 0.0374 (15) 0.0416 (15) 0.0438 (16) 0.0071 (12) 0.0158 (13) 0.0069 (13)
C10 0.0384 (17) 0.077 (2) 0.064 (2) −0.0040 (16) 0.0102 (15) 0.0218 (18)
C11 0.0446 (19) 0.091 (3) 0.090 (3) 0.0035 (19) 0.0309 (19) 0.033 (2)
C12 0.063 (2) 0.070 (2) 0.075 (2) 0.0108 (18) 0.0376 (19) 0.0292 (19)
C13 0.070 (2) 0.069 (2) 0.0462 (19) 0.0116 (18) 0.0191 (17) 0.0152 (16)
C14 0.0410 (16) 0.0525 (17) 0.0438 (17) −0.0021 (13) 0.0090 (13) 0.0037 (13) C15 0.0324 (15) 0.0426 (16) 0.0574 (18) −0.0012 (12) 0.0137 (13) −0.0031 (13)
C16 0.0490 (19) 0.079 (2) 0.055 (2) 0.0127 (17) 0.0189 (16) 0.0057 (18)
supporting information
sup-6
Acta Cryst. (2006). E62, m7–m9C18 0.0378 (19) 0.099 (3) 0.090 (3) 0.0100 (19) 0.0136 (18) −0.018 (2)
C19 0.0388 (19) 0.136 (4) 0.074 (3) 0.010 (2) 0.0028 (18) −0.019 (3)
C20 0.0388 (17) 0.087 (2) 0.055 (2) 0.0065 (17) 0.0059 (15) 0.0005 (18)
C21 0.0365 (14) 0.0319 (13) 0.0380 (15) 0.0003 (11) −0.0032 (12) 0.0004 (11)
C22 0.0390 (17) 0.062 (2) 0.057 (2) 0.0047 (14) 0.0054 (14) 0.0055 (16)
C23 0.0381 (17) 0.072 (2) 0.069 (2) 0.0141 (16) −0.0046 (16) 0.0063 (18)
C24 0.054 (2) 0.060 (2) 0.055 (2) 0.0025 (16) −0.0144 (16) 0.0074 (16)
C25 0.063 (2) 0.059 (2) 0.0434 (18) −0.0018 (17) −0.0071 (15) 0.0124 (15)
C26 0.0432 (17) 0.0530 (18) 0.0429 (17) −0.0008 (14) 0.0036 (13) 0.0109 (14)
Geometric parameters (Å, º)
Sn1—O1 2.1317 (19) C13—H13A 0.9700
Sn1—C21 2.144 (2) C13—H13B 0.9700
Sn1—C9 2.152 (3) C14—H14A 0.9700
Sn1—C15 2.155 (3) C14—H14B 0.9700
Sn1—O2i 2.769 (2) C15—C20 1.497 (4)
N1—O4 1.208 (4) C15—C16 1.531 (4)
N1—O5 1.228 (4) C15—H15 0.9800
N1—C6 1.469 (5) C16—C17 1.524 (4)
O1—C1 1.274 (3) C16—H16A 0.9700
O2—C1 1.217 (3) C16—H16B 0.9700
O3—C3 1.358 (4) C17—C18 1.475 (5)
O3—C2 1.428 (3) C17—H17A 0.9700
C1—C2 1.518 (4) C17—H17B 0.9700
C2—H2A 0.9700 C18—C19 1.510 (5)
C2—H2B 0.9700 C18—H18A 0.9700
C3—C8 1.381 (4) C18—H18B 0.9700
C3—C4 1.399 (4) C19—C20 1.521 (4)
C4—C5 1.367 (5) C19—H19A 0.9700
C4—H4 0.9300 C19—H19B 0.9700
C5—C6 1.365 (5) C20—H20A 0.9700
C5—H5A 0.9300 C20—H20B 0.9700
C6—C7 1.378 (4) C21—C22 1.528 (4)
C7—C8 1.378 (4) C21—C26 1.529 (4)
C7—H7 0.9300 C21—H21 0.9800
C8—H8 0.9300 C22—C23 1.528 (4)
C9—C14 1.524 (4) C22—H22A 0.9700
C9—C10 1.527 (4) C22—H22B 0.9700
C9—H9 0.9800 C23—C24 1.509 (4)
C10—C11 1.517 (4) C23—H23A 0.9700
C10—H10A 0.9700 C23—H23B 0.9700
C10—H10B 0.9700 C24—C25 1.503 (4)
C11—C12 1.520 (4) C24—H24A 0.9700
C11—H11A 0.9700 C24—H24B 0.9700
C11—H11B 0.9700 C25—C26 1.518 (4)
C12—C13 1.506 (5) C25—H25A 0.9700
C12—H12B 0.9700 C26—H26A 0.9700
C13—C14 1.527 (4) C26—H26B 0.9700
O1—Sn1—C21 89.83 (9) C9—C14—H14B 109.4
O1—Sn1—C9 99.86 (9) C13—C14—H14B 109.4
C21—Sn1—C9 116.16 (10) H14A—C14—H14B 108.0
O1—Sn1—C15 98.68 (9) C20—C15—C16 110.5 (2)
C21—Sn1—C15 115.26 (11) C20—C15—Sn1 115.4 (2)
C9—Sn1—C15 124.93 (11) C16—C15—Sn1 112.8 (2)
O1—Sn1—O2i 170.61 (11) C20—C15—H15 105.8
C21—Sn1—O2i 81.49 (9) C16—C15—H15 105.8
C9—Sn1—O2i 87.27 (9) Sn1—C15—H15 105.8
C15—Sn1—O2i 81.95 (9) C17—C16—C15 110.8 (3)
O4—N1—O5 124.9 (4) C17—C16—H16A 109.5
O4—N1—C6 118.5 (3) C15—C16—H16A 109.5
O5—N1—C6 116.6 (4) C17—C16—H16B 109.5
C1—O1—Sn1 132.96 (19) C15—C16—H16B 109.5
C3—O3—C2 118.1 (2) H16A—C16—H16B 108.1
O2—C1—O1 127.1 (3) C18—C17—C16 112.2 (3)
O2—C1—C2 118.8 (3) C18—C17—H17A 109.2
O1—C1—C2 114.0 (3) C16—C17—H17A 109.2
O3—C2—C1 115.0 (2) C18—C17—H17B 109.2
O3—C2—H2A 108.5 C16—C17—H17B 109.2
C1—C2—H2A 108.5 H17A—C17—H17B 107.9
O3—C2—H2B 108.5 C17—C18—C19 111.3 (3)
C1—C2—H2B 108.5 C17—C18—H18A 109.4
H2A—C2—H2B 107.5 C19—C18—H18A 109.4
O3—C3—C8 125.4 (3) C17—C18—H18B 109.4
O3—C3—C4 115.2 (3) C19—C18—H18B 109.4
C8—C3—C4 119.3 (3) H18A—C18—H18B 108.0
C5—C4—C3 120.3 (3) C18—C19—C20 111.5 (3)
C5—C4—H4 119.9 C18—C19—H19A 109.3
C3—C4—H4 119.9 C20—C19—H19A 109.3
C6—C5—C4 119.8 (3) C18—C19—H19B 109.3
C6—C5—H5A 120.1 C20—C19—H19B 109.3
C4—C5—H5A 120.1 H19A—C19—H19B 108.0
C5—C6—C7 120.9 (3) C15—C20—C19 112.0 (3)
C5—C6—N1 120.2 (3) C15—C20—H20A 109.2
C7—C6—N1 118.9 (3) C19—C20—H20A 109.2
C8—C7—C6 119.8 (3) C15—C20—H20B 109.2
C8—C7—H7 120.1 C19—C20—H20B 109.2
C6—C7—H7 120.1 H20A—C20—H20B 107.9
C7—C8—C3 119.8 (3) C22—C21—C26 110.6 (2)
C7—C8—H8 120.1 C22—C21—Sn1 112.46 (18)
C3—C8—H8 120.1 C26—C21—Sn1 111.92 (17)
C14—C9—C10 109.6 (2) C22—C21—H21 107.2
C14—C9—Sn1 114.66 (18) C26—C21—H21 107.2
supporting information
sup-8
Acta Cryst. (2006). E62, m7–m9C14—C9—H9 107.0 C23—C22—C21 111.5 (2)
C10—C9—H9 107.0 C23—C22—H22A 109.3
Sn1—C9—H9 107.0 C21—C22—H22A 109.3
C11—C10—C9 111.4 (3) C23—C22—H22B 109.3
C11—C10—H10A 109.3 C21—C22—H22B 109.3
C9—C10—H10A 109.3 H22A—C22—H22B 108.0
C11—C10—H10B 109.3 C24—C23—C22 111.3 (3)
C9—C10—H10B 109.3 C24—C23—H23A 109.4
H10A—C10—H10B 108.0 C22—C23—H23A 109.4
C10—C11—C12 111.1 (3) C24—C23—H23B 109.4
C10—C11—H11A 109.4 C22—C23—H23B 109.4
C12—C11—H11A 109.4 H23A—C23—H23B 108.0
C10—C11—H11B 109.4 C25—C24—C23 111.4 (3)
C12—C11—H11B 109.4 C25—C24—H24A 109.3
H11A—C11—H11B 108.0 C23—C24—H24A 109.3
C13—C12—C11 112.0 (3) C25—C24—H24B 109.3
C13—C12—H12A 109.2 C23—C24—H24B 109.3
C11—C12—H12A 109.2 H24A—C24—H24B 108.0
C13—C12—H12B 109.2 C24—C25—C26 110.9 (3)
C11—C12—H12B 109.2 C24—C25—H25A 109.5
H12A—C12—H12B 107.9 C26—C25—H25A 109.5
C12—C13—C14 111.1 (3) C24—C25—H25B 109.5
C12—C13—H13A 109.4 C26—C25—H25B 109.5
C14—C13—H13A 109.4 H25A—C25—H25B 108.0
C12—C13—H13B 109.4 C25—C26—C21 112.6 (2)
C14—C13—H13B 109.4 C25—C26—H26A 109.1
H13A—C13—H13B 108.0 C21—C26—H26A 109.1
C9—C14—C13 111.1 (2) C25—C26—H26B 109.1
C9—C14—H14A 109.4 C21—C26—H26B 109.1
C13—C14—H14A 109.4 H26A—C26—H26B 107.8
C21—Sn1—O1—C1 175.0 (3) C10—C11—C12—C13 54.4 (4)
C9—Sn1—O1—C1 −68.5 (3) C11—C12—C13—C14 −54.6 (4)
C15—Sn1—O1—C1 59.5 (3) C10—C9—C14—C13 −57.1 (3)
Sn1—O1—C1—O2 13.8 (4) Sn1—C9—C14—C13 177.1 (2)
Sn1—O1—C1—C2 −164.07 (19) C12—C13—C14—C9 56.4 (3)
C3—O3—C2—C1 −80.2 (3) O1—Sn1—C15—C20 −98.5 (2)
O2—C1—C2—O3 166.4 (3) C21—Sn1—C15—C20 167.5 (2)
O1—C1—C2—O3 −15.6 (4) C9—Sn1—C15—C20 10.0 (3)
C2—O3—C3—C8 9.8 (4) O1—Sn1—C15—C16 29.7 (2)
C2—O3—C3—C4 −168.9 (3) C21—Sn1—C15—C16 −64.2 (2)
O3—C3—C4—C5 176.7 (3) C9—Sn1—C15—C16 138.2 (2)
C8—C3—C4—C5 −2.1 (5) C20—C15—C16—C17 −54.5 (4)
C3—C4—C5—C6 −0.3 (5) Sn1—C15—C16—C17 174.8 (2)
C4—C5—C6—C7 2.0 (5) C15—C16—C17—C18 55.7 (4)
C4—C5—C6—N1 −177.5 (3) C16—C17—C18—C19 −55.5 (4)
O4—N1—C6—C5 179.6 (3) C17—C18—C19—C20 54.6 (5)
O4—N1—C6—C7 0.0 (5) Sn1—C15—C20—C19 −176.0 (2)
O5—N1—C6—C7 −179.8 (3) C18—C19—C20—C15 −54.8 (5)
C5—C6—C7—C8 −1.4 (5) O1—Sn1—C21—C22 68.5 (2)
N1—C6—C7—C8 178.2 (3) C9—Sn1—C21—C22 −32.4 (2)
C6—C7—C8—C3 −0.9 (5) C15—Sn1—C21—C22 168.00 (19)
O3—C3—C8—C7 −176.0 (3) O1—Sn1—C21—C26 −56.69 (18)
C4—C3—C8—C7 2.7 (4) C9—Sn1—C21—C26 −157.60 (18)
O1—Sn1—C9—C14 99.3 (2) C15—Sn1—C21—C26 42.8 (2)
C21—Sn1—C9—C14 −166.04 (19) C26—C21—C22—C23 −53.0 (3)
C15—Sn1—C9—C14 −8.7 (3) Sn1—C21—C22—C23 −178.9 (2)
O1—Sn1—C9—C10 −25.7 (2) C21—C22—C23—C24 55.2 (4)
C21—Sn1—C9—C10 69.0 (2) C22—C23—C24—C25 −56.8 (4)
C15—Sn1—C9—C10 −133.62 (19) C23—C24—C25—C26 56.3 (4)
C14—C9—C10—C11 57.1 (3) C24—C25—C26—C21 −55.1 (3)
Sn1—C9—C10—C11 −175.2 (2) C22—C21—C26—C25 53.3 (3)
C9—C10—C11—C12 −55.7 (4) Sn1—C21—C26—C25 179.5 (2)