# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 _journal_name_full 'Perkin Transactions 1' #=========================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Dr. R. Alan Howie' _publ_contact_author_address ; Department of Chemistry University of Aberdeen Meston Walk Aberdeen AB24 3UE Scotland UK ; _publ_contact_author_email r.a.howie@abdn.ac.uk _publ_contact_author_fax 44(1224)272921 _publ_contact_author_phone 44(1224)272907 #=========================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Hydroxyl group interactions in stannylated carbohydrates. Structures and thermal stabilities of 5-deoxy-5-C-(Ph3Sn)-1,2-O-isopropylidene-alpha-D-xylofuranose, 5-deoxy-5-C-(IPh2)-1,2-O-isopropylidene-alpha-D- and -L-xylofuranose and 5-deoxy-5-C-(I2Ph)-1,2-O-isopropylidene-alpha-D- and -L-xylofuranose. ; loop_ _publ_author_name _publ_author_address 'Burnett, Lynne A.' ; Department of Chemistry University of Aberdeen Meston Walk Aberdeen AB24 3UE Scotland UK ; 'Ferreira, Vitor F.' ; Departamento de Quimica Inorganica Instituto de Quimica Universidade Federal do Rio de Janeiro CP 68563 21945-970 Rio de Janeiro RJ Brazil ; 'Howie, R. Alan' ; Department of Chemistry University of Aberdeen Meston Walk Aberdeen AB24 3UE Scotland UK ; 'Rufino, Helena' ; Department of Chemistry University of Aberdeen Meston Walk Aberdeen AB24 3UE Scotland UK ; 'Skakle, Janet M.S.' ; Department of Chemistry University of Aberdeen Meston Walk Aberdeen AB24 3UE Scotland UK ; 'Wardell, James L.' ; Department of Chemistry University of Aberdeen Meston Walk Aberdeen AB24 3UE Scotland UK and Departamento de Quimica Inorganica Instituto de Quimica Universidade Federal do Rio de Janeiro CP 68563 21945-970 Rio de Janeiro RJ Brazil ; 'Wardell, Solange M.S.V' ; Departamento de Quimica Organica Instituto de Quimica Universidade Federal Fluminense 24020-150 Niteroi Rio de Janeiro Brazil ; data_(D)-3 _database_code_CSD 185948 _publ_requested_journal test _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Deoxy-1,2-O-isopropylidene-5-C-(triphenylstannyl)-alpha- D-xylofuranose ; _chemical_name_common ? _chemical_formula_moiety 'C26 H28 O4 Sn' _chemical_formula_sum 'C26 H28 O4 Sn' _chemical_formula_weight 523.17 _chemical_melting_point '428-430 (dec)' _chemical_absolute_configuration rmad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.820(10) _cell_length_b 6.658(6) _cell_length_c 14.427(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.78(6) _cell_angle_gamma 90.00 _cell_volume 1220.1(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 14 _cell_measurement_theta_min 7.85 _cell_measurement_theta_max 11.5 _exptl_crystal_preparation 'from MeOH:CHCl3 2:1 v/v as solvent' _exptl_crystal_description rhomb _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 1.075 _exptl_absorpt_correction_type none # SHELXL-97 Tmin/max calc. (from xstl. dims.) 0.6377/0.8301 - #no corrn. applied # _exptl_absorpt_correction_T_min 0.6377 # _exptl_absorpt_correction_T_max 0.8301 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nicolet P3' _diffrn_measurement_method \q-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4310 _diffrn_reflns_av_R_equivalents 0.1248 _diffrn_reflns_av_sigmaI/netI 0.0636 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4215 _reflns_number_gt 3366 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Nicolet P3 software (Nicolet, 1980)' _computing_cell_refinement 'Nicolet P3 software (Nicolet, 1980)' _computing_data_reduction 'RDNIC (Howie, 1980)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-H refined anisotropically. H in calculated positions and refined with a riding model. Correct absolute structure confirmed by Flack x parameter of -0.06(6) vvs 1.03(6) for inverted model although only monoclinic symmetry unique reflections available. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1060P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(6) _refine_ls_number_reflns 4215 _refine_ls_number_parameters 283 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0889 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.1659 _refine_ls_wR_factor_gt 0.1513 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 0.76484(4) 0.00000(13) 0.23761(4) 0.0457(2) Uani 1 d . . . C1 C 0.4673(10) -0.1002(17) 0.3771(8) 0.057(3) Uani 1 d . . . H1 H 0.4745 -0.1353 0.4436 0.069 Uiso 1 calc R . . C2 C 0.3933(11) 0.0784(17) 0.3561(9) 0.064(3) Uani 1 d . . . H2 H 0.3634 0.1238 0.4115 0.077 Uiso 1 calc R . . C3 C 0.4599(11) 0.2373(19) 0.3186(10) 0.049(3) Uani 1 d . . . H3A H 0.4201 0.3118 0.2668 0.058 Uiso 1 calc R . . C4 C 0.5483(8) 0.1144(14) 0.2858(8) 0.044(2) Uani 1 d . . . H4 H 0.5217 0.0577 0.2244 0.053 Uiso 1 calc R . . C5 C 0.6514(8) 0.2093(17) 0.2785(8) 0.058(3) Uani 1 d . . . H5A H 0.6788 0.2676 0.3385 0.070 Uiso 1 calc R . . H5B H 0.6413 0.3173 0.2330 0.070 Uiso 1 calc R . . C6 C 0.3108(8) -0.2014(17) 0.2875(9) 0.060(3) Uani 1 d . . . C7 C 0.2819(12) -0.280(2) 0.1914(12) 0.093(5) Uani 1 d . . . H7A H 0.2118 -0.2375 0.1677 0.139 Uiso 1 calc R . . H7B H 0.2851 -0.4238 0.1923 0.139 Uiso 1 calc R . . H7C H 0.3302 -0.2286 0.1518 0.139 Uiso 1 calc R . . C8 C 0.2407(13) -0.275(3) 0.3550(14) 0.117(7) Uani 1 d . . . H8A H 0.2584 -0.2082 0.4139 0.175 Uiso 1 calc R . . H8B H 0.2500 -0.4174 0.3636 0.175 Uiso 1 calc R . . H8C H 0.1686 -0.2475 0.3307 0.175 Uiso 1 calc R . . O1 O 0.4186(8) -0.2574(14) 0.3218(8) 0.064(3) Uani 1 d . . . O2 O 0.3154(5) 0.009(2) 0.2846(5) 0.073(2) Uani 1 d . . . O3 O 0.5028(8) 0.3684(12) 0.3924(6) 0.070(2) Uani 1 d . . . H3 H 0.4927 0.4854 0.3758 0.105 Uiso 1 calc R . . O4 O 0.5632(5) -0.0487(9) 0.3516(5) 0.053(2) Uani 1 d . . . C9 C 0.8840(8) 0.1601(17) 0.1796(8) 0.054(3) Uani 1 d . . . C10 C 0.9913(9) 0.1327(19) 0.2097(9) 0.066(3) Uani 1 d . . . H10 H 1.0121 0.0389 0.2564 0.079 Uiso 1 calc R . . C11 C 1.0676(10) 0.242(3) 0.1719(12) 0.086(4) Uani 1 d . . . H11 H 1.1386 0.2225 0.1934 0.103 Uiso 1 calc R . . C12 C 1.0372(11) 0.377(2) 0.1030(12) 0.088(4) Uani 1 d . . . H12 H 1.0883 0.4513 0.0780 0.105 Uiso 1 calc R . . C13 C 0.9337(12) 0.408(2) 0.0695(10) 0.085(4) Uani 1 d . . . H13 H 0.9143 0.4990 0.0214 0.102 Uiso 1 calc R . . C14 C 0.8577(10) 0.2998(19) 0.1089(9) 0.069(3) Uani 1 d . . . H14 H 0.7870 0.3219 0.0871 0.083 Uiso 1 calc R . . C15 C 0.8300(8) -0.1936(15) 0.3466(7) 0.050(2) Uani 1 d . . . C16 C 0.8089(9) -0.180(2) 0.4388(8) 0.067(3) Uani 1 d . . . H16 H 0.7654 -0.0774 0.4551 0.081 Uiso 1 calc R . . C17 C 0.8511(9) -0.314(2) 0.5064(9) 0.073(4) Uani 1 d . . . H17 H 0.8364 -0.3002 0.5674 0.088 Uiso 1 calc R . . C18 C 0.9141(10) -0.468(3) 0.4850(9) 0.079(5) Uani 1 d . . . H18 H 0.9415 -0.5586 0.5308 0.094 Uiso 1 calc R . . C19 C 0.9370(11) -0.487(4) 0.3944(9) 0.089(4) Uani 1 d . . . H19 H 0.9798 -0.5907 0.3790 0.107 Uiso 1 calc R . . C20 C 0.8963(11) -0.3514(19) 0.3273(9) 0.072(3) Uani 1 d . . . H20 H 0.9132 -0.3649 0.2670 0.087 Uiso 1 calc R . . C21 C 0.6865(8) -0.1871(15) 0.1281(7) 0.047(2) Uani 1 d . . . C22 C 0.6048(8) -0.3116(15) 0.1461(8) 0.053(2) Uani 1 d . . . H22 H 0.5837 -0.3125 0.2052 0.063 Uiso 1 calc R . . C23 C 0.5549(10) -0.4336(17) 0.0771(9) 0.069(4) Uani 1 d . . . H23 H 0.4993 -0.5147 0.0896 0.082 Uiso 1 calc R . . C24 C 0.5869(10) -0.4368(19) -0.0114(9) 0.074(4) Uani 1 d . . . H24 H 0.5537 -0.5203 -0.0581 0.089 Uiso 1 calc R . . C25 C 0.6684(10) -0.314(2) -0.0285(8) 0.068(3) Uani 1 d . . . H25 H 0.6906 -0.3142 -0.0873 0.082 Uiso 1 calc R . . C26 C 0.7171(9) -0.1911(18) 0.0402(8) 0.057(3) Uani 1 d . . . H26 H 0.7720 -0.1088 0.0273 0.069 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.0438(3) 0.0505(3) 0.0420(3) -0.0001(7) 0.00264(19) -0.0023(7) C1 0.080(9) 0.045(6) 0.048(6) 0.007(5) 0.009(6) 0.005(6) C2 0.081(9) 0.053(6) 0.066(8) -0.004(5) 0.031(7) 0.011(6) C3 0.072(9) 0.034(6) 0.041(6) -0.008(5) 0.010(6) 0.011(6) C4 0.048(6) 0.035(5) 0.049(6) 0.003(4) 0.002(5) 0.010(4) C5 0.057(6) 0.057(7) 0.062(7) -0.005(5) 0.009(5) 0.002(5) C6 0.047(6) 0.054(7) 0.080(8) 0.009(6) 0.011(6) 0.005(5) C7 0.086(10) 0.089(11) 0.099(11) -0.004(9) -0.006(9) -0.020(8) C8 0.085(11) 0.110(13) 0.172(19) -0.002(13) 0.076(12) -0.009(9) O1 0.069(7) 0.044(5) 0.078(6) -0.002(4) 0.013(5) 0.005(4) O2 0.054(3) 0.065(5) 0.098(5) -0.004(9) -0.003(4) 0.016(8) O3 0.101(7) 0.047(5) 0.063(5) -0.013(4) 0.015(5) 0.009(4) O4 0.052(4) 0.044(6) 0.063(4) 0.003(3) 0.003(3) 0.011(3) C9 0.053(6) 0.059(6) 0.049(6) -0.008(5) 0.003(5) 0.002(5) C10 0.052(7) 0.075(8) 0.068(8) -0.007(6) 0.000(6) -0.002(6) C11 0.049(7) 0.103(11) 0.110(12) -0.009(10) 0.025(7) -0.006(7) C12 0.062(9) 0.097(10) 0.112(12) 0.000(10) 0.040(8) -0.022(7) C13 0.100(11) 0.093(10) 0.067(8) 0.012(7) 0.025(8) -0.027(8) C14 0.062(7) 0.074(8) 0.074(8) 0.016(7) 0.014(6) -0.003(6) C15 0.049(6) 0.050(6) 0.048(6) 0.001(5) 0.001(5) -0.005(4) C16 0.059(7) 0.090(9) 0.052(7) -0.002(6) 0.007(6) 0.004(6) C17 0.055(7) 0.114(11) 0.048(6) 0.013(7) 0.003(5) 0.001(7) C18 0.080(7) 0.083(14) 0.070(7) 0.033(9) -0.001(6) -0.004(8) C19 0.108(9) 0.079(9) 0.075(7) -0.004(13) -0.008(7) 0.031(13) C20 0.089(9) 0.065(8) 0.058(7) -0.006(6) -0.006(6) 0.017(7) C21 0.050(6) 0.046(6) 0.044(5) -0.003(4) 0.001(5) 0.005(4) C22 0.056(6) 0.046(6) 0.055(6) 0.002(5) 0.009(5) -0.005(5) C23 0.060(7) 0.065(9) 0.079(8) -0.007(5) 0.004(6) -0.008(5) C24 0.076(8) 0.075(10) 0.065(7) -0.022(6) -0.018(6) 0.005(6) C25 0.079(8) 0.082(9) 0.042(6) -0.008(6) 0.002(6) 0.004(7) C26 0.053(6) 0.069(7) 0.051(6) 0.005(5) 0.013(5) 0.000(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sn1 C15 2.116(10) . ? Sn1 C9 2.125(12) . ? Sn1 C21 2.151(10) . ? Sn1 C5 2.154(11) . ? Sn1 O4 3.262(8) . ? C1 O4 1.373(14) . ? C1 O1 1.409(14) . ? C1 C2 1.527(15) . ? C1 H1 0.9800 . ? C2 O2 1.412(15) . ? C2 C3 1.506(19) . ? C2 H2 0.9800 . ? C3 O3 1.428(15) . ? C3 C4 1.525(15) . ? C3 H3A 0.9800 . ? C4 O4 1.438(11) . ? C4 C5 1.481(15) . ? C4 H4 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O2 1.403(16) . ? C6 O1 1.452(14) . ? C6 C7 1.48(2) . ? C6 C8 1.494(19) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? O3 H3 0.8200 . ? C9 C14 1.387(16) . ? C9 C10 1.397(15) . ? C10 C11 1.389(19) . ? C10 H10 0.9300 . ? C11 C12 1.36(2) . ? C11 H11 0.9300 . ? C12 C13 1.36(2) . ? C12 H12 0.9300 . ? C13 C14 1.393(18) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.396(16) . ? C15 C20 1.402(16) . ? C16 C17 1.380(18) . ? C16 H16 0.9300 . ? C17 C18 1.36(2) . ? C17 H17 0.9300 . ? C18 C19 1.383(19) . ? C18 H18 0.9300 . ? C19 C20 1.37(2) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C26 1.377(15) . ? C21 C22 1.388(15) . ? C22 C23 1.373(16) . ? C22 H22 0.9300 . ? C23 C24 1.394(19) . ? C23 H23 0.9300 . ? C24 C25 1.376(19) . ? C24 H24 0.9300 . ? C25 C26 1.369(16) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 Sn1 C9 111.5(4) . . ? C15 Sn1 C21 106.9(4) . . ? C9 Sn1 C21 106.8(4) . . ? C15 Sn1 C5 113.8(4) . . ? C9 Sn1 C5 109.4(4) . . ? C21 Sn1 C5 108.1(4) . . ? C15 Sn1 O4 79.9(3) . . ? C9 Sn1 O4 155.4(3) . . ? C21 Sn1 O4 89.4(3) . . ? C5 Sn1 O4 46.8(3) . . ? O4 C1 O1 112.2(10) . . ? O4 C1 C2 107.9(9) . . ? O1 C1 C2 104.5(9) . . ? O4 C1 H1 110.7 . . ? O1 C1 H1 110.7 . . ? C2 C1 H1 110.7 . . ? O2 C2 C3 110.3(11) . . ? O2 C2 C1 104.4(9) . . ? C3 C2 C1 104.5(10) . . ? O2 C2 H2 112.4 . . ? C3 C2 H2 112.4 . . ? C1 C2 H2 112.4 . . ? O3 C3 C2 110.0(11) . . ? O3 C3 C4 109.4(10) . . ? C2 C3 C4 102.5(9) . . ? O3 C3 H3A 111.5 . . ? C2 C3 H3A 111.5 . . ? C4 C3 H3A 111.5 . . ? O4 C4 C5 109.2(8) . . ? O4 C4 C3 103.8(9) . . ? C5 C4 C3 120.1(9) . . ? O4 C4 H4 107.7 . . ? C5 C4 H4 107.7 . . ? C3 C4 H4 107.7 . . ? C4 C5 Sn1 112.7(7) . . ? C4 C5 H5A 109.1 . . ? Sn1 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? Sn1 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? O2 C6 O1 102.9(8) . . ? O2 C6 C7 109.3(11) . . ? O1 C6 C7 109.5(11) . . ? O2 C6 C8 112.3(11) . . ? O1 C6 C8 108.8(11) . . ? C7 C6 C8 113.5(12) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 O1 C6 109.3(10) . . ? C6 O2 C2 109.5(9) . . ? C3 O3 H3 109.5 . . ? C1 O4 C4 108.8(8) . . ? C1 O4 Sn1 163.5(7) . . ? C4 O4 Sn1 68.6(5) . . ? C14 C9 C10 116.5(11) . . ? C14 C9 Sn1 120.7(8) . . ? C10 C9 Sn1 122.8(9) . . ? C11 C10 C9 121.7(13) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C12 C11 C10 119.1(13) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 121.8(13) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C12 C13 C14 118.6(14) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C9 C14 C13 122.2(12) . . ? C9 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C16 C15 C20 116.1(11) . . ? C16 C15 Sn1 124.1(9) . . ? C20 C15 Sn1 119.9(8) . . ? C17 C16 C15 121.4(12) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C16 121.0(12) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 119.3(16) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C20 C19 C18 119.9(18) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C15 122.3(13) . . ? C19 C20 H20 118.8 . . ? C15 C20 H20 118.8 . . ? C26 C21 C22 118.5(10) . . ? C26 C21 Sn1 121.6(8) . . ? C22 C21 Sn1 119.8(8) . . ? C23 C22 C21 120.5(11) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 120.4(11) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C25 C24 C23 118.7(11) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C26 C25 C24 120.6(11) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C21 121.3(11) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C1 C2 O2 114.3(9) . . . . ? O1 C1 C2 O2 -5.3(12) . . . . ? O4 C1 C2 C3 -1.5(13) . . . . ? O1 C1 C2 C3 -121.2(10) . . . . ? O2 C2 C3 O3 153.5(10) . . . . ? C1 C2 C3 O3 -94.8(11) . . . . ? O2 C2 C3 C4 -90.3(11) . . . . ? C1 C2 C3 C4 21.4(12) . . . . ? O3 C3 C4 O4 82.9(11) . . . . ? C2 C3 C4 O4 -33.8(11) . . . . ? O3 C3 C4 C5 -39.3(15) . . . . ? C2 C3 C4 C5 -156.0(11) . . . . ? O4 C4 C5 Sn1 57.5(10) . . . . ? C3 C4 C5 Sn1 177.0(8) . . . . ? C15 Sn1 C5 C4 -76.1(9) . . . . ? C9 Sn1 C5 C4 158.5(8) . . . . ? C21 Sn1 C5 C4 42.5(9) . . . . ? O4 Sn1 C5 C4 -28.8(6) . . . . ? O4 C1 O1 C6 -130.3(10) . . . . ? C2 C1 O1 C6 -13.6(13) . . . . ? O2 C6 O1 C1 27.5(12) . . . . ? C7 C6 O1 C1 143.6(11) . . . . ? C8 C6 O1 C1 -91.8(13) . . . . ? O1 C6 O2 C2 -31.2(12) . . . . ? C7 C6 O2 C2 -147.6(11) . . . . ? C8 C6 O2 C2 85.6(13) . . . . ? C3 C2 O2 C6 135.0(10) . . . . ? C1 C2 O2 C6 23.2(12) . . . . ? O1 C1 O4 C4 93.7(10) . . . . ? C2 C1 O4 C4 -20.9(12) . . . . ? O1 C1 O4 Sn1 16(3) . . . . ? C2 C1 O4 Sn1 -99(2) . . . . ? C5 C4 O4 C1 163.9(9) . . . . ? C3 C4 O4 C1 34.7(11) . . . . ? C5 C4 O4 Sn1 -33.5(6) . . . . ? C3 C4 O4 Sn1 -162.6(8) . . . . ? C15 Sn1 O4 C1 -110(2) . . . . ? C9 Sn1 O4 C1 130(2) . . . . ? C21 Sn1 O4 C1 -2(2) . . . . ? C5 Sn1 O4 C1 113(2) . . . . ? C15 Sn1 O4 C4 166.3(6) . . . . ? C9 Sn1 O4 C4 46.0(9) . . . . ? C21 Sn1 O4 C4 -86.4(6) . . . . ? C5 Sn1 O4 C4 29.4(6) . . . . ? C15 Sn1 C9 C14 -178.1(9) . . . . ? C21 Sn1 C9 C14 65.4(10) . . . . ? C5 Sn1 C9 C14 -51.3(10) . . . . ? O4 Sn1 C9 C14 -64.1(13) . . . . ? C15 Sn1 C9 C10 1.7(11) . . . . ? C21 Sn1 C9 C10 -114.8(9) . . . . ? C5 Sn1 C9 C10 128.4(10) . . . . ? O4 Sn1 C9 C10 115.6(10) . . . . ? C14 C9 C10 C11 1.0(19) . . . . ? Sn1 C9 C10 C11 -178.8(10) . . . . ? C9 C10 C11 C12 -1(2) . . . . ? C10 C11 C12 C13 -1(3) . . . . ? C11 C12 C13 C14 1(2) . . . . ? C10 C9 C14 C13 0.0(19) . . . . ? Sn1 C9 C14 C13 179.7(11) . . . . ? C12 C13 C14 C9 -1(2) . . . . ? C9 Sn1 C15 C16 119.5(10) . . . . ? C21 Sn1 C15 C16 -124.1(9) . . . . ? C5 Sn1 C15 C16 -4.8(11) . . . . ? O4 Sn1 C15 C16 -37.8(9) . . . . ? C9 Sn1 C15 C20 -62.6(10) . . . . ? C21 Sn1 C15 C20 53.8(10) . . . . ? C5 Sn1 C15 C20 173.1(9) . . . . ? O4 Sn1 C15 C20 140.1(9) . . . . ? C20 C15 C16 C17 0.0(18) . . . . ? Sn1 C15 C16 C17 177.9(10) . . . . ? C15 C16 C17 C18 -1(2) . . . . ? C16 C17 C18 C19 1(2) . . . . ? C17 C18 C19 C20 0(3) . . . . ? C18 C19 C20 C15 -1(3) . . . . ? C16 C15 C20 C19 1(2) . . . . ? Sn1 C15 C20 C19 -177.1(13) . . . . ? C15 Sn1 C21 C26 -118.3(9) . . . . ? C9 Sn1 C21 C26 1.1(10) . . . . ? C5 Sn1 C21 C26 118.7(9) . . . . ? O4 Sn1 C21 C26 162.4(8) . . . . ? C15 Sn1 C21 C22 59.9(9) . . . . ? C9 Sn1 C21 C22 179.4(8) . . . . ? C5 Sn1 C21 C22 -63.0(9) . . . . ? O4 Sn1 C21 C22 -19.3(8) . . . . ? C26 C21 C22 C23 -0.9(16) . . . . ? Sn1 C21 C22 C23 -179.3(8) . . . . ? C21 C22 C23 C24 1.2(17) . . . . ? C22 C23 C24 C25 -0.7(18) . . . . ? C23 C24 C25 C26 0.1(19) . . . . ? C24 C25 C26 C21 0.2(19) . . . . ? C22 C21 C26 C25 0.2(16) . . . . ? Sn1 C21 C26 C25 178.6(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O1 0.82 2.06 2.849(13) 161.2 1_565 C1 H1 O3 0.98 2.34 3.303(14) 165.5 2_646 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.099 _refine_diff_density_min -1.613 _refine_diff_density_rms 0.135 #===END data_(D)-4 _database_code_CSD 185949 _publ_requested_journal test _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-deoxy-5-C-(iododiphenylstannyl)-1,2-O-isopropylidene-alpha-D -xylofuranose ; _chemical_name_common ? _chemical_formula_moiety 'C20 H23 I O4 Sn' _chemical_formula_sum 'C20 H23 I O4 Sn' _chemical_formula_weight 572.97 _chemical_melting_point '427-429 (dec)' _chemical_absolute_configuration rmad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.566(14) _cell_length_b 10.366(10) _cell_length_c 12.983(19) _cell_angle_alpha 104.99(9) _cell_angle_beta 111.71(11) _cell_angle_gamma 65.14(9) _cell_volume 1077(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 14 _cell_measurement_theta_min 8.35 _cell_measurement_theta_max 9.95 _exptl_crystal_preparation 'from 60-80 pet. ether:CHCl3 as solvent' _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.767 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 2.639 _exptl_absorpt_correction_type none # SHELXL-97 Tmin/max calc. (from xstl. dims.) 0.3004/0.5944 - #no corrn. applied # _exptl_absorpt_correction_T_min 0.3004 # _exptl_absorpt_correction_T_max 0.5944 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nicolet P3' _diffrn_measurement_method \q-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3825 _diffrn_reflns_av_R_equivalents 0.0079 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3823 _reflns_number_gt 3510 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Nicolet P3 software (Nicolet, 1980)' _computing_cell_refinement 'Nicolet P3 software (Nicolet, 1980)' _computing_data_reduction 'RDNIC (Howie, 1980)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-H renined anisotropically and H in calculated positions and refined with a riding model. Unique hemi-sphere of intensity data only but Flack x for inverted structure of 0.24(4) vvs 0.01(4) for coordinates given here confirms correct absolute structure. The extreme anisotropy of displacement of C19A and C20A is attributed to libration of the phenyl group of which they are part. The librational motion is perceived as having two components as partial rotation about the C-Sn bond and a fan like wagging with motion in a direction perpendicular to the plane of the phenyl ring. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0866P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(4) _refine_ls_number_reflns 3823 _refine_ls_number_parameters 473 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 0.00002(8) -0.00004(7) 0.00000(6) 0.0442(2) Uani 1 d . . . I1 I -0.05531(13) 0.17966(10) -0.14670(8) 0.0686(3) Uani 1 d . . . C1 C -0.0339(15) 0.0298(14) 0.3193(11) 0.049(3) Uani 1 d . . . H1 H -0.1152 -0.0151 0.2856 0.059 Uiso 1 calc R . . C2 C 0.1374(14) -0.0835(12) 0.3569(10) 0.043(2) Uani 1 d . . . H2 H 0.1370 -0.1783 0.3555 0.051 Uiso 1 calc R . . C3 C 0.2144(14) -0.0814(13) 0.2776(10) 0.045(3) Uani 1 d . . . H3B H 0.3313 -0.1068 0.3110 0.054 Uiso 1 calc R . . C4 C 0.1317(15) 0.0723(12) 0.2526(9) 0.043(3) Uani 1 d . . . H4 H 0.1758 0.1344 0.3155 0.051 Uiso 1 calc R . . C5 C 0.1337(18) 0.1009(16) 0.1451(11) 0.055(3) Uani 1 d . . . H5A H 0.2446 0.0664 0.1443 0.066 Uiso 1 calc R . . H5B H 0.0884 0.2034 0.1422 0.066 Uiso 1 calc R . . C6 C 0.0766(17) 0.0657(14) 0.5134(11) 0.053(3) Uani 1 d . . . C7 C 0.124(2) 0.1838(19) 0.5911(13) 0.074(4) Uani 1 d . . . H7A H 0.2224 0.1440 0.6487 0.111 Uiso 1 calc R . . H7B H 0.0404 0.2450 0.6243 0.111 Uiso 1 calc R . . H7C H 0.1416 0.2384 0.5505 0.111 Uiso 1 calc R . . C8 C 0.035(2) -0.0210(19) 0.5674(13) 0.071(4) Uani 1 d . . . H8A H 0.0134 -0.0996 0.5147 0.107 Uiso 1 calc R . . H8B H -0.0597 0.0390 0.5906 0.107 Uiso 1 calc R . . H8C H 0.1232 -0.0572 0.6313 0.107 Uiso 1 calc R . . O1 O -0.0572(12) 0.1215(10) 0.4187(7) 0.060(3) Uani 1 d . . . O2 O 0.2030(10) -0.0219(9) 0.4658(7) 0.049(2) Uani 1 d . . . O3 O 0.1762(11) -0.1706(8) 0.1770(7) 0.050(2) Uani 1 d . . . H3 H 0.2597 -0.2312 0.1656 0.075 Uiso 1 d R . . O4 O -0.0328(9) 0.1013(9) 0.2450(7) 0.0464(19) Uani 1 d . . . C9 C 0.0988(17) -0.2073(14) -0.0876(10) 0.052(3) Uani 1 d . . . C10 C 0.0952(17) -0.3258(13) -0.0616(12) 0.052(3) Uani 1 d . . . H10 H 0.0609 -0.3183 -0.0013 0.062 Uiso 1 calc R . . C11 C 0.1432(19) -0.4575(16) -0.1260(17) 0.072(5) Uani 1 d . . . H11 H 0.1374 -0.5367 -0.1091 0.087 Uiso 1 calc R . . C12 C 0.198(2) -0.4734(19) -0.2129(15) 0.080(5) Uani 1 d . . . H12 H 0.2317 -0.5624 -0.2543 0.096 Uiso 1 calc R . . C13 C 0.203(3) -0.361(2) -0.2370(15) 0.086(5) Uani 1 d . . . H13 H 0.2409 -0.3695 -0.2958 0.103 Uiso 1 calc R . . C14 C 0.151(2) -0.2266(17) -0.1745(13) 0.074(5) Uani 1 d . . . H14 H 0.1536 -0.1478 -0.1946 0.089 Uiso 1 calc R . . C15 C -0.2402(15) 0.0238(14) -0.0081(11) 0.049(3) Uani 1 d . . . C16 C -0.2581(17) -0.0591(14) 0.0464(11) 0.051(3) Uani 1 d . . . H16 H -0.1679 -0.1247 0.0894 0.062 Uiso 1 calc R . . C17 C -0.415(2) -0.0462(16) 0.0382(14) 0.066(4) Uani 1 d . . . H17 H -0.4274 -0.1045 0.0755 0.080 Uiso 1 calc R . . C18 C -0.546(2) 0.0476(18) -0.0219(15) 0.071(4) Uani 1 d . . . H18 H -0.6479 0.0571 -0.0239 0.085 Uiso 1 calc R . . C19 C -0.531(2) 0.131(2) -0.0814(17) 0.081(5) Uani 1 d . . . H19 H -0.6224 0.1946 -0.1248 0.097 Uiso 1 calc R . . C20 C -0.378(2) 0.1204(17) -0.0767(15) 0.072(4) Uani 1 d . . . H20 H -0.3669 0.1752 -0.1176 0.086 Uiso 1 calc R . . Sn1A Sn -0.58001(8) 0.41210(8) 0.39600(7) 0.0455(2) Uani 1 d . . . I1A I -0.88677(10) 0.51180(10) 0.42810(8) 0.0633(3) Uani 1 d . . . C1A C -0.3777(15) 0.5821(12) 0.2315(11) 0.048(3) Uani 1 d . . . H1A H -0.3285 0.6234 0.3061 0.058 Uiso 1 calc R . . C2A C -0.2766(14) 0.4242(11) 0.2098(11) 0.043(3) Uani 1 d . . . H2A H -0.1668 0.3970 0.2614 0.051 Uiso 1 calc R . . C3A C -0.3756(13) 0.3456(11) 0.2195(10) 0.041(2) Uani 1 d . . . H3C H -0.3569 0.2515 0.1745 0.049 Uiso 1 calc R . . C4A C -0.5487(13) 0.4495(12) 0.1785(11) 0.045(3) Uani 1 d . . . H4A H -0.5856 0.4393 0.0966 0.054 Uiso 1 calc R . . C5A C -0.6672(13) 0.4376(15) 0.2211(10) 0.046(3) Uani 1 d . . . H5A1 H -0.6969 0.3563 0.1784 0.055 Uiso 1 calc R . . H5A2 H -0.7640 0.5230 0.2083 0.055 Uiso 1 calc R . . C6A C -0.3036(14) 0.5393(12) 0.0723(12) 0.048(3) Uani 1 d . . . C7A C -0.420(3) 0.556(2) -0.0454(17) 0.090(6) Uani 1 d . . . H7A1 H -0.3897 0.4680 -0.0931 0.135 Uiso 1 calc R . . H7A2 H -0.4169 0.6314 -0.0736 0.135 Uiso 1 calc R . . H7A3 H -0.5277 0.5796 -0.0435 0.135 Uiso 1 calc R . . C8A C -0.144(2) 0.5511(19) 0.0884(16) 0.074(5) Uani 1 d . . . H8A1 H -0.0812 0.5464 0.1654 0.110 Uiso 1 calc R . . H8A2 H -0.1639 0.6406 0.0671 0.110 Uiso 1 calc R . . H8A3 H -0.0869 0.4736 0.0427 0.110 Uiso 1 calc R . . O1A O -0.3806(14) 0.6468(9) 0.1508(10) 0.068(3) Uani 1 d . . . O2A O -0.2805(11) 0.4058(9) 0.0982(8) 0.054(2) Uani 1 d . . . O3A O -0.3422(9) 0.3369(10) 0.3339(8) 0.048(2) Uani 1 d . . . H3A H -0.2669 0.2621 0.3515 0.073 Uiso 1 d R . . O4A O -0.5327(10) 0.5891(8) 0.2226(8) 0.050(2) Uani 1 d . . . C9A C -0.4853(14) 0.1971(15) 0.4336(12) 0.051(3) Uani 1 d . . . C10A C -0.471(3) 0.1640(19) 0.5348(17) 0.080(5) Uani 1 d . . . H10A H -0.5105 0.2377 0.5871 0.096 Uiso 1 calc R . . C11A C -0.401(3) 0.026(2) 0.560(2) 0.092(6) Uani 1 d . . . H11A H -0.3854 0.0058 0.6299 0.111 Uiso 1 calc R . . C12A C -0.354(2) -0.0846(19) 0.476(2) 0.096(7) Uani 1 d . . . H12A H -0.3103 -0.1791 0.4912 0.115 Uiso 1 calc R . . C13A C -0.369(2) -0.0585(17) 0.3754(17) 0.077(5) Uani 1 d . . . H13A H -0.3346 -0.1338 0.3223 0.092 Uiso 1 calc R . . C14A C -0.4370(19) 0.0835(16) 0.3514(14) 0.062(4) Uani 1 d . . . H14A H -0.4504 0.1028 0.2816 0.074 Uiso 1 calc R . . C15A C -0.4728(15) 0.5391(14) 0.5318(11) 0.052(3) Uani 1 d . . . C16A C -0.558(2) 0.672(2) 0.5745(18) 0.093(6) Uani 1 d . . . H16A H -0.6685 0.7134 0.5418 0.111 Uiso 1 calc R . . C17A C -0.480(3) 0.7468(19) 0.6660(17) 0.092(6) Uani 1 d . . . H17A H -0.5403 0.8373 0.6934 0.111 Uiso 1 calc R . . C18A C -0.329(3) 0.696(2) 0.714(2) 0.107(8) Uani 1 d . . . H18A H -0.2805 0.7499 0.7749 0.128 Uiso 1 calc R . . C19A C -0.238(3) 0.563(5) 0.676(4) 0.28(4) Uani 1 d . . . H19A H -0.1277 0.5236 0.7093 0.334 Uiso 1 calc R . . C20A C -0.317(3) 0.490(4) 0.586(3) 0.25(3) Uani 1 d . . . H20A H -0.2564 0.3975 0.5614 0.295 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.0504(5) 0.0403(4) 0.0434(4) 0.0017(3) 0.0172(4) -0.0171(4) I1 0.0917(7) 0.0589(6) 0.0599(6) 0.0164(4) 0.0304(5) -0.0196(5) C1 0.037(6) 0.047(7) 0.050(7) 0.003(5) 0.010(5) -0.007(5) C2 0.037(6) 0.036(6) 0.047(6) 0.008(5) 0.013(5) -0.004(5) C3 0.034(6) 0.042(6) 0.035(6) 0.001(5) 0.005(5) 0.001(5) C4 0.059(7) 0.039(6) 0.035(6) 0.002(4) 0.014(5) -0.024(5) C5 0.063(8) 0.058(8) 0.051(7) 0.010(6) 0.011(6) -0.032(7) C6 0.059(8) 0.042(7) 0.046(7) -0.007(5) 0.019(6) -0.013(6) C7 0.081(11) 0.076(10) 0.053(8) 0.000(7) 0.009(7) -0.032(9) C8 0.086(11) 0.079(10) 0.055(8) 0.015(7) 0.029(8) -0.025(9) O1 0.054(5) 0.056(6) 0.040(5) 0.000(4) 0.018(4) 0.008(4) O2 0.042(5) 0.047(5) 0.043(4) 0.006(4) 0.007(4) -0.007(4) O3 0.049(5) 0.033(4) 0.049(5) 0.000(3) 0.014(4) -0.001(4) O4 0.035(4) 0.041(4) 0.045(4) 0.013(3) 0.014(3) 0.008(3) C9 0.060(8) 0.045(7) 0.033(6) -0.002(5) 0.004(5) -0.015(6) C10 0.053(7) 0.034(6) 0.064(8) 0.000(6) 0.020(6) -0.012(5) C11 0.053(8) 0.045(8) 0.099(12) -0.004(8) 0.008(8) -0.018(6) C12 0.079(11) 0.061(10) 0.074(11) -0.029(8) 0.016(9) -0.028(9) C13 0.113(15) 0.083(12) 0.052(9) -0.020(8) 0.036(9) -0.033(11) C14 0.104(13) 0.051(8) 0.050(8) 0.002(6) 0.022(8) -0.015(8) C15 0.043(7) 0.047(7) 0.041(6) -0.002(5) 0.003(5) -0.014(5) C16 0.054(7) 0.050(7) 0.057(7) 0.003(6) 0.015(6) -0.028(6) C17 0.068(9) 0.056(8) 0.077(10) -0.010(7) 0.030(8) -0.027(8) C18 0.058(9) 0.068(9) 0.083(11) -0.007(8) 0.019(8) -0.031(8) C19 0.051(9) 0.075(11) 0.089(13) 0.010(10) 0.012(8) -0.005(8) C20 0.065(10) 0.054(8) 0.083(11) 0.008(7) 0.017(8) -0.013(7) Sn1A 0.0371(4) 0.0408(4) 0.0509(5) 0.0000(3) 0.0108(3) -0.0121(3) I1A 0.0445(5) 0.0766(6) 0.0661(6) -0.0092(5) 0.0207(4) -0.0260(4) C1A 0.046(7) 0.030(6) 0.054(7) 0.001(5) 0.009(5) -0.007(5) C2A 0.034(6) 0.024(5) 0.061(7) 0.002(5) 0.011(5) -0.006(4) C3A 0.038(6) 0.023(5) 0.058(7) 0.003(5) 0.013(5) -0.010(4) C4A 0.033(6) 0.034(6) 0.055(7) -0.001(5) 0.008(5) -0.010(5) C5A 0.020(5) 0.064(7) 0.044(6) 0.012(5) -0.002(4) -0.012(5) C6A 0.039(6) 0.029(5) 0.073(8) 0.005(5) 0.017(6) -0.010(5) C7A 0.090(13) 0.083(12) 0.085(12) 0.027(10) -0.001(10) -0.033(11) C8A 0.062(9) 0.075(10) 0.102(13) 0.028(9) 0.014(8) -0.040(8) O1A 0.080(7) 0.029(4) 0.103(8) 0.007(5) 0.044(6) -0.014(4) O2A 0.057(5) 0.038(4) 0.075(6) 0.006(4) 0.028(5) -0.019(4) O3A 0.028(4) 0.052(5) 0.060(5) 0.018(4) 0.012(4) -0.004(3) O4A 0.042(4) 0.023(4) 0.075(6) 0.001(4) 0.020(4) -0.003(3) C9A 0.032(6) 0.057(7) 0.064(8) 0.008(6) 0.008(5) -0.022(5) C10A 0.100(13) 0.054(9) 0.091(12) 0.016(8) 0.043(11) -0.016(9) C11A 0.100(15) 0.071(12) 0.106(15) 0.034(11) 0.026(12) -0.022(10) C12A 0.081(13) 0.046(9) 0.14(2) 0.036(11) -0.004(12) -0.026(9) C13A 0.100(13) 0.051(8) 0.099(13) 0.005(8) 0.031(10) -0.046(9) C14A 0.066(9) 0.055(8) 0.077(10) 0.007(7) 0.020(7) -0.037(7) C15A 0.034(6) 0.046(7) 0.058(7) -0.001(6) 0.008(5) -0.008(5) C16A 0.064(10) 0.063(10) 0.104(14) -0.013(9) -0.005(9) -0.018(8) C17A 0.106(15) 0.053(9) 0.089(13) -0.013(9) -0.001(11) -0.040(10) C18A 0.101(17) 0.084(13) 0.097(14) -0.015(11) -0.022(12) -0.057(13) C19A 0.060(15) 0.29(5) 0.25(5) -0.16(4) -0.03(2) -0.03(2) C20A 0.043(11) 0.19(3) 0.26(4) -0.16(3) -0.023(16) 0.010(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sn1 C5 2.145(14) . ? Sn1 C9 2.151(13) . ? Sn1 C15 2.171(14) . ? Sn1 I1 2.764(4) . ? Sn1 O3 2.825(10) . ? C1 O4 1.366(17) . ? C1 O1 1.421(16) . ? C1 C2 1.545(16) . ? C1 H1 0.9800 . ? C2 O2 1.419(15) . ? C2 C3 1.479(18) . ? C2 H2 0.9800 . ? C3 O3 1.414(14) . ? C3 C4 1.512(17) . ? C3 H3B 0.9800 . ? C4 O4 1.442(15) . ? C4 C5 1.508(17) . ? C4 H4 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O2 1.417(16) . ? C6 O1 1.437(17) . ? C6 C7 1.49(2) . ? C6 C8 1.52(2) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? O3 H3 0.8200 . ? C9 C14 1.34(2) . ? C9 C10 1.372(19) . ? C10 C11 1.39(2) . ? C10 H10 0.9300 . ? C11 C12 1.36(3) . ? C11 H11 0.9300 . ? C12 C13 1.31(3) . ? C12 H12 0.9300 . ? C13 C14 1.40(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.339(19) . ? C15 C20 1.42(2) . ? C16 C17 1.42(2) . ? C16 H16 0.9300 . ? C17 C18 1.33(2) . ? C17 H17 0.9300 . ? C18 C19 1.38(3) . ? C18 H18 0.9300 . ? C19 C20 1.40(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? Sn1A C15A 2.119(13) . ? Sn1A C9A 2.136(14) . ? Sn1A C5A 2.156(12) . ? Sn1A O3A 2.443(9) . ? Sn1A I1A 2.826(5) . ? C1A O1A 1.369(17) . ? C1A O4A 1.415(16) . ? C1A C2A 1.525(15) . ? C1A H1A 0.9800 . ? C2A O2A 1.400(16) . ? C2A C3A 1.539(16) . ? C2A H2A 0.9800 . ? C3A O3A 1.418(15) . ? C3A C4A 1.527(15) . ? C3A H3C 0.9800 . ? C4A O4A 1.462(14) . ? C4A C5A 1.491(18) . ? C4A H4A 0.9800 . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A O2A 1.417(15) . ? C6A O1A 1.450(17) . ? C6A C8A 1.511(19) . ? C6A C7A 1.52(2) . ? C7A H7A1 0.9600 . ? C7A H7A2 0.9600 . ? C7A H7A3 0.9600 . ? C8A H8A1 0.9600 . ? C8A H8A2 0.9600 . ? C8A H8A3 0.9600 . ? O3A H3A 0.8200 . ? C9A C10A 1.39(2) . ? C9A C14A 1.41(2) . ? C10A C11A 1.37(3) . ? C10A H10A 0.9300 . ? C11A C12A 1.41(3) . ? C11A H11A 0.9300 . ? C12A C13A 1.35(3) . ? C12A H12A 0.9300 . ? C13A C14A 1.40(2) . ? C13A H13A 0.9300 . ? C14A H14A 0.9300 . ? C15A C20A 1.32(2) . ? C15A C16A 1.37(2) . ? C16A C17A 1.38(2) . ? C16A H16A 0.9300 . ? C17A C18A 1.27(3) . ? C17A H17A 0.9300 . ? C18A C19A 1.36(4) . ? C18A H18A 0.9300 . ? C19A C20A 1.37(3) . ? C19A H19A 0.9300 . ? C20A H20A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Sn1 C9 125.6(6) . . ? C5 Sn1 C15 118.1(5) . . ? C9 Sn1 C15 106.5(5) . . ? C5 Sn1 I1 96.5(4) . . ? C9 Sn1 I1 101.5(4) . . ? C15 Sn1 I1 104.0(4) . . ? C5 Sn1 O3 66.6(4) . . ? C9 Sn1 O3 78.5(4) . . ? C15 Sn1 O3 97.9(4) . . ? I1 Sn1 O3 157.1(2) . . ? O4 C1 O1 111.2(11) . . ? O4 C1 C2 107.1(10) . . ? O1 C1 C2 104.7(10) . . ? O4 C1 H1 111.2 . . ? O1 C1 H1 111.2 . . ? C2 C1 H1 111.2 . . ? O2 C2 C3 111.2(10) . . ? O2 C2 C1 102.6(9) . . ? C3 C2 C1 102.8(10) . . ? O2 C2 H2 113.1 . . ? C3 C2 H2 113.1 . . ? C1 C2 H2 113.1 . . ? O3 C3 C2 110.8(11) . . ? O3 C3 C4 108.1(9) . . ? C2 C3 C4 102.5(9) . . ? O3 C3 H3B 111.7 . . ? C2 C3 H3B 111.7 . . ? C4 C3 H3B 111.7 . . ? O4 C4 C5 108.5(10) . . ? O4 C4 C3 101.9(9) . . ? C5 C4 C3 116.5(11) . . ? O4 C4 H4 109.8 . . ? C5 C4 H4 109.8 . . ? C3 C4 H4 109.8 . . ? C4 C5 Sn1 112.7(8) . . ? C4 C5 H5A 109.1 . . ? Sn1 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? Sn1 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? O2 C6 O1 103.3(10) . . ? O2 C6 C7 107.9(13) . . ? O1 C6 C7 110.3(12) . . ? O2 C6 C8 111.6(12) . . ? O1 C6 C8 109.4(12) . . ? C7 C6 C8 113.8(13) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 O1 C6 110.0(9) . . ? C6 O2 C2 109.3(9) . . ? C3 O3 Sn1 108.8(7) . . ? C3 O3 H3 109.5 . . ? Sn1 O3 H3 110.1 . . ? C1 O4 C4 109.4(9) . . ? C14 C9 C10 116.8(13) . . ? C14 C9 Sn1 123.2(11) . . ? C10 C9 Sn1 119.7(10) . . ? C9 C10 C11 119.7(15) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 121.8(17) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C13 C12 C11 118.5(15) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C14 120.4(18) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C9 C14 C13 122.8(17) . . ? C9 C14 H14 118.6 . . ? C13 C14 H14 118.6 . . ? C16 C15 C20 120.1(13) . . ? C16 C15 Sn1 119.8(10) . . ? C20 C15 Sn1 120.0(11) . . ? C15 C16 C17 119.6(14) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 121.2(16) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 120.2(16) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C20 120.5(16) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C15 118.4(17) . . ? C19 C20 H20 120.8 . . ? C15 C20 H20 120.8 . . ? C15A Sn1A C9A 109.7(5) . . ? C15A Sn1A C5A 127.8(5) . . ? C9A Sn1A C5A 115.8(5) . . ? C15A Sn1A O3A 87.1(4) . . ? C9A Sn1A O3A 84.8(4) . . ? C5A Sn1A O3A 73.3(4) . . ? C15A Sn1A I1A 99.1(4) . . ? C9A Sn1A I1A 100.7(3) . . ? C5A Sn1A I1A 96.3(3) . . ? O3A Sn1A I1A 169.6(2) . . ? O1A C1A O4A 112.5(11) . . ? O1A C1A C2A 105.5(11) . . ? O4A C1A C2A 106.9(10) . . ? O1A C1A H1A 110.5 . . ? O4A C1A H1A 110.5 . . ? C2A C1A H1A 110.5 . . ? O2A C2A C1A 104.2(10) . . ? O2A C2A C3A 109.2(9) . . ? C1A C2A C3A 103.6(9) . . ? O2A C2A H2A 113.0 . . ? C1A C2A H2A 113.0 . . ? C3A C2A H2A 113.0 . . ? O3A C3A C4A 107.9(9) . . ? O3A C3A C2A 108.9(9) . . ? C4A C3A C2A 102.4(9) . . ? O3A C3A H3C 112.4 . . ? C4A C3A H3C 112.4 . . ? C2A C3A H3C 112.4 . . ? O4A C4A C5A 109.1(10) . . ? O4A C4A C3A 102.5(8) . . ? C5A C4A C3A 115.1(11) . . ? O4A C4A H4A 110.0 . . ? C5A C4A H4A 110.0 . . ? C3A C4A H4A 110.0 . . ? C4A C5A Sn1A 114.2(8) . . ? C4A C5A H5A1 108.7 . . ? Sn1A C5A H5A1 108.7 . . ? C4A C5A H5A2 108.7 . . ? Sn1A C5A H5A2 108.7 . . ? H5A1 C5A H5A2 107.6 . . ? O2A C6A O1A 105.6(10) . . ? O2A C6A C8A 111.3(11) . . ? O1A C6A C8A 108.9(12) . . ? O2A C6A C7A 107.1(12) . . ? O1A C6A C7A 109.0(13) . . ? C8A C6A C7A 114.6(15) . . ? C6A C7A H7A1 109.5 . . ? C6A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C6A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C6A C8A H8A1 109.5 . . ? C6A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C6A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C1A O1A C6A 109.8(9) . . ? C2A O2A C6A 107.8(9) . . ? C3A O3A Sn1A 115.0(6) . . ? C3A O3A H3A 109.5 . . ? Sn1A O3A H3A 119.6 . . ? C1A O4A C4A 110.7(8) . . ? C10A C9A C14A 118.5(14) . . ? C10A C9A Sn1A 122.8(11) . . ? C14A C9A Sn1A 118.7(10) . . ? C11A C10A C9A 121.9(18) . . ? C11A C10A H10A 119.1 . . ? C9A C10A H10A 119.1 . . ? C10A C11A C12A 118(2) . . ? C10A C11A H11A 121.0 . . ? C12A C11A H11A 121.0 . . ? C13A C12A C11A 122.3(16) . . ? C13A C12A H12A 118.8 . . ? C11A C12A H12A 118.8 . . ? C12A C13A C14A 119.2(17) . . ? C12A C13A H13A 120.4 . . ? C14A C13A H13A 120.4 . . ? C13A C14A C9A 119.9(15) . . ? C13A C14A H14A 120.1 . . ? C9A C14A H14A 120.1 . . ? C20A C15A C16A 114.9(16) . . ? C20A C15A Sn1A 121.2(13) . . ? C16A C15A Sn1A 123.8(11) . . ? C15A C16A C17A 120.4(17) . . ? C15A C16A H16A 119.8 . . ? C17A C16A H16A 119.8 . . ? C18A C17A C16A 123(2) . . ? C18A C17A H17A 118.7 . . ? C16A C17A H17A 118.7 . . ? C17A C18A C19A 119.5(18) . . ? C17A C18A H18A 120.2 . . ? C19A C18A H18A 120.2 . . ? C18A C19A C20A 117(2) . . ? C18A C19A H19A 121.3 . . ? C20A C19A H19A 121.3 . . ? C15A C20A C19A 125(2) . . ? C15A C20A H20A 117.4 . . ? C19A C20A H20A 117.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C1 C2 O2 104.6(11) . . . . ? O1 C1 C2 O2 -13.6(13) . . . . ? O4 C1 C2 C3 -10.9(13) . . . . ? O1 C1 C2 C3 -129.1(11) . . . . ? O2 C2 C3 O3 166.7(9) . . . . ? C1 C2 C3 O3 -84.2(11) . . . . ? O2 C2 C3 C4 -78.2(11) . . . . ? C1 C2 C3 C4 30.9(12) . . . . ? O3 C3 C4 O4 77.0(11) . . . . ? C2 C3 C4 O4 -40.1(11) . . . . ? O3 C3 C4 C5 -40.9(15) . . . . ? C2 C3 C4 C5 -158.0(10) . . . . ? O4 C4 C5 Sn1 -49.1(12) . . . . ? C3 C4 C5 Sn1 65.1(14) . . . . ? C9 Sn1 C5 C4 -93.5(11) . . . . ? C15 Sn1 C5 C4 47.7(12) . . . . ? I1 Sn1 C5 C4 157.3(9) . . . . ? O3 Sn1 C5 C4 -38.8(9) . . . . ? O4 C1 O1 C6 -121.2(11) . . . . ? C2 C1 O1 C6 -5.9(14) . . . . ? O2 C6 O1 C1 23.1(14) . . . . ? C7 C6 O1 C1 138.2(13) . . . . ? C8 C6 O1 C1 -95.9(14) . . . . ? O1 C6 O2 C2 -33.0(13) . . . . ? C7 C6 O2 C2 -149.7(12) . . . . ? C8 C6 O2 C2 84.5(13) . . . . ? C3 C2 O2 C6 138.3(10) . . . . ? C1 C2 O2 C6 29.0(12) . . . . ? C2 C3 O3 Sn1 117.1(8) . . . . ? C4 C3 O3 Sn1 5.5(11) . . . . ? C5 Sn1 O3 C3 19.3(8) . . . . ? C9 Sn1 O3 C3 156.6(8) . . . . ? C15 Sn1 O3 C3 -98.1(8) . . . . ? I1 Sn1 O3 C3 64.3(9) . . . . ? O1 C1 O4 C4 98.7(11) . . . . ? C2 C1 O4 C4 -15.2(13) . . . . ? C5 C4 O4 C1 158.2(10) . . . . ? C3 C4 O4 C1 34.7(11) . . . . ? C5 Sn1 C9 C14 -92.3(14) . . . . ? C15 Sn1 C9 C14 122.9(14) . . . . ? I1 Sn1 C9 C14 14.4(14) . . . . ? O3 Sn1 C9 C14 -142.2(14) . . . . ? C5 Sn1 C9 C10 94.1(12) . . . . ? C15 Sn1 C9 C10 -50.7(12) . . . . ? I1 Sn1 C9 C10 -159.2(10) . . . . ? O3 Sn1 C9 C10 44.2(10) . . . . ? C14 C9 C10 C11 -1(2) . . . . ? Sn1 C9 C10 C11 173.2(11) . . . . ? C9 C10 C11 C12 2(2) . . . . ? C10 C11 C12 C13 -1(3) . . . . ? C11 C12 C13 C14 0(3) . . . . ? C10 C9 C14 C13 -1(3) . . . . ? Sn1 C9 C14 C13 -174.5(15) . . . . ? C12 C13 C14 C9 1(3) . . . . ? C5 Sn1 C15 C16 -80.5(11) . . . . ? C9 Sn1 C15 C16 67.4(11) . . . . ? I1 Sn1 C15 C16 174.2(9) . . . . ? O3 Sn1 C15 C16 -12.8(11) . . . . ? C5 Sn1 C15 C20 103.6(12) . . . . ? C9 Sn1 C15 C20 -108.5(11) . . . . ? I1 Sn1 C15 C20 -1.8(11) . . . . ? O3 Sn1 C15 C20 171.3(11) . . . . ? C20 C15 C16 C17 -2(2) . . . . ? Sn1 C15 C16 C17 -178.1(10) . . . . ? C15 C16 C17 C18 -1(2) . . . . ? C16 C17 C18 C19 3(2) . . . . ? C17 C18 C19 C20 -2(3) . . . . ? C18 C19 C20 C15 -1(3) . . . . ? C16 C15 C20 C19 3(2) . . . . ? Sn1 C15 C20 C19 178.9(12) . . . . ? O1A C1A C2A O2A -20.4(13) . . . . ? O4A C1A C2A O2A 99.6(11) . . . . ? O1A C1A C2A C3A -134.7(11) . . . . ? O4A C1A C2A C3A -14.6(13) . . . . ? O2A C2A C3A O3A 167.0(9) . . . . ? C1A C2A C3A O3A -82.5(11) . . . . ? O2A C2A C3A C4A -79.0(11) . . . . ? C1A C2A C3A C4A 31.5(12) . . . . ? O3A C3A C4A O4A 78.0(11) . . . . ? C2A C3A C4A O4A -36.8(11) . . . . ? O3A C3A C4A C5A -40.3(13) . . . . ? C2A C3A C4A C5A -155.1(10) . . . . ? O4A C4A C5A Sn1A -71.9(11) . . . . ? C3A C4A C5A Sn1A 42.6(13) . . . . ? C15A Sn1A C5A C4A 51.2(11) . . . . ? C9A Sn1A C5A C4A -97.0(10) . . . . ? O3A Sn1A C5A C4A -21.4(8) . . . . ? I1A Sn1A C5A C4A 157.9(9) . . . . ? O4A C1A O1A C6A -110.2(11) . . . . ? C2A C1A O1A C6A 6.1(14) . . . . ? O2A C6A O1A C1A 10.3(14) . . . . ? C8A C6A O1A C1A -109.4(13) . . . . ? C7A C6A O1A C1A 125.0(13) . . . . ? C1A C2A O2A C6A 27.2(12) . . . . ? C3A C2A O2A C6A 137.4(9) . . . . ? O1A C6A O2A C2A -23.9(12) . . . . ? C8A C6A O2A C2A 94.1(14) . . . . ? C7A C6A O2A C2A -140.0(13) . . . . ? C4A C3A O3A Sn1A 20.4(10) . . . . ? C2A C3A O3A Sn1A 130.8(7) . . . . ? C15A Sn1A O3A C3A -131.2(8) . . . . ? C9A Sn1A O3A C3A 118.6(8) . . . . ? C5A Sn1A O3A C3A -0.2(7) . . . . ? I1A Sn1A O3A C3A -3.8(17) . . . . ? O1A C1A O4A C4A 106.1(11) . . . . ? C2A C1A O4A C4A -9.3(14) . . . . ? C5A C4A O4A C1A 151.9(10) . . . . ? C3A C4A O4A C1A 29.5(13) . . . . ? C15A Sn1A C9A C10A 46.9(14) . . . . ? C5A Sn1A C9A C10A -159.4(13) . . . . ? O3A Sn1A C9A C10A 131.9(13) . . . . ? I1A Sn1A C9A C10A -57.0(13) . . . . ? C15A Sn1A C9A C14A -134.1(10) . . . . ? C5A Sn1A C9A C14A 19.6(11) . . . . ? O3A Sn1A C9A C14A -49.1(10) . . . . ? I1A Sn1A C9A C14A 122.0(9) . . . . ? C14A C9A C10A C11A 5(3) . . . . ? Sn1A C9A C10A C11A -176.0(16) . . . . ? C9A C10A C11A C12A -5(3) . . . . ? C10A C11A C12A C13A 3(3) . . . . ? C11A C12A C13A C14A -1(3) . . . . ? C12A C13A C14A C9A 1(2) . . . . ? C10A C9A C14A C13A -3(2) . . . . ? Sn1A C9A C14A C13A 177.7(11) . . . . ? C9A Sn1A C15A C20A 41(3) . . . . ? C5A Sn1A C15A C20A -108(3) . . . . ? O3A Sn1A C15A C20A -42(3) . . . . ? I1A Sn1A C15A C20A 146(3) . . . . ? C9A Sn1A C15A C16A -134.6(16) . . . . ? C5A Sn1A C15A C16A 75.8(18) . . . . ? O3A Sn1A C15A C16A 142.0(17) . . . . ? I1A Sn1A C15A C16A -29.7(17) . . . . ? C20A C15A C16A C17A 2(4) . . . . ? Sn1A C15A C16A C17A 177.6(17) . . . . ? C15A C16A C17A C18A 0(4) . . . . ? C16A C17A C18A C19A -1(5) . . . . ? C17A C18A C19A C20A 0(8) . . . . ? C16A C15A C20A C19A -3(7) . . . . ? Sn1A C15A C20A C19A -179(5) . . . . ? C18A C19A C20A C15A 2(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O4A 0.82 2.12 2.832(12) 145.8 1_645 O3A H3A O1 0.82 1.95 2.750(13) 163.9 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.608 _refine_diff_density_min -1.565 _refine_diff_density_rms 0.151 #===END data_(L)-4 _database_code_CSD 185950 _publ_requested_journal test _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-deoxy-5-C-(iododiphenylstannyl)-1,2-O-isopropylidene-alpha-L- xylofuranose ; _chemical_name_common ? _chemical_formula_moiety 'C20 H23 I O4 Sn' _chemical_formula_sum 'C20 H23 I O4 Sn' _chemical_formula_weight 572.97 _chemical_melting_point '427-429 (dec)' _chemical_absolute_configuration rmad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.4450(3) _cell_length_b 10.2372(3) _cell_length_c 12.8723(6) _cell_angle_alpha 105.1242(12) _cell_angle_beta 111.3979(12) _cell_angle_gamma 65.334(3) _cell_volume 1044.38(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14728 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 30.32 _exptl_crystal_preparation 'from 60-80 pet. ether:CHCl3 as solvent' _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.822 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 2.722 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV; Blessing, 1995, 1997)' # compare next with SHELXL-97 calc. 0.7725 and 0.9351 _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 0.960 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15230 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.1138 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 30.82 _reflns_number_total 9477 _reflns_number_gt 6865 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-H refined anisotropically. H in calculated positions and refined with a riding model. Absolute structure from 4113 Friedel pairs. The extreme anisotropy of displacement of C19A and C20A is attributed to libration of the phenyl group of which they are part. The librational motion is perceived as having two components as partial rotation about the C-Sn bond and a fan like wagging with motion in a direction perpendicular to the plane of the phenyl ring. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0381P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(3) _refine_ls_number_reflns 9477 _refine_ls_number_parameters 473 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn -0.22693(6) 0.18416(6) 0.23907(5) 0.02734(15) Uani 1 d . . . I1 I -0.17005(7) 0.00396(6) 0.38801(5) 0.04072(18) Uani 1 d . . . C1 C -0.1806(12) 0.1490(9) -0.0804(8) 0.030(2) Uani 1 d . . . H1 H -0.0947 0.1933 -0.0470 0.035 Uiso 1 calc R . . C2 C -0.3527(11) 0.2653(9) -0.1177(7) 0.0266(19) Uani 1 d . . . H2 H -0.3508 0.3627 -0.1163 0.032 Uiso 1 calc R . . C3 C -0.4394(10) 0.2654(9) -0.0400(7) 0.0256(19) Uani 1 d . . . H3B H -0.5599 0.2930 -0.0747 0.031 Uiso 1 calc R . . C4 C -0.3540(9) 0.1089(9) -0.0130(7) 0.0254(19) Uani 1 d . . . H4 H -0.3974 0.0438 -0.0781 0.031 Uiso 1 calc R . . C5 C -0.3616(12) 0.0803(11) 0.0930(8) 0.036(2) Uani 1 d . . . H5A H -0.3161 -0.0255 0.0959 0.043 Uiso 1 calc R . . H5B H -0.4767 0.1169 0.0928 0.043 Uiso 1 calc R . . C6 C -0.2951(12) 0.1156(10) -0.2749(8) 0.032(2) Uani 1 d . . . C7 C -0.3385(13) -0.0058(11) -0.3545(9) 0.043(3) Uani 1 d . . . H7A H -0.3578 -0.0630 -0.3142 0.065 Uiso 1 calc R . . H7B H -0.2488 -0.0679 -0.3866 0.065 Uiso 1 calc R . . H7C H -0.4374 0.0334 -0.4151 0.065 Uiso 1 calc R . . C8 C -0.2450(13) 0.2040(12) -0.3241(9) 0.044(3) Uani 1 d . . . H8A H -0.3365 0.2505 -0.3859 0.066 Uiso 1 calc R . . H8B H -0.1522 0.1399 -0.3525 0.066 Uiso 1 calc R . . H8C H -0.2139 0.2784 -0.2655 0.066 Uiso 1 calc R . . O1 O -0.1603(7) 0.0544(6) -0.1793(5) 0.0337(15) Uani 1 d . . . O2 O -0.4213(7) 0.2033(6) -0.2267(5) 0.0256(13) Uani 1 d . . . O3 O -0.3953(7) 0.3536(6) 0.0636(5) 0.0306(14) Uani 1 d . . . H3 H -0.4745 0.4314 0.0677 0.046 Uiso 1 d R . . O4 O -0.1843(7) 0.0774(6) -0.0028(5) 0.0279(13) Uani 1 d . . . C9 C -0.3277(11) 0.3949(10) 0.3269(8) 0.032(2) Uani 1 d . . . C10 C -0.3184(12) 0.5140(10) 0.3009(9) 0.038(2) Uani 1 d . . . H10 H -0.2772 0.5041 0.2409 0.045 Uiso 1 calc R . . C11 C -0.3705(11) 0.6483(10) 0.3644(9) 0.036(2) Uani 1 d . . . H11 H -0.3698 0.7312 0.3447 0.043 Uiso 1 calc R . . C12 C -0.4228(12) 0.6631(11) 0.4546(8) 0.043(3) Uani 1 d . . . H12 H -0.4549 0.7549 0.4984 0.052 Uiso 1 calc R . . C13 C -0.4283(14) 0.5449(13) 0.4810(9) 0.049(3) Uani 1 d . . . H13 H -0.4642 0.5551 0.5437 0.059 Uiso 1 calc R . . C14 C -0.3825(12) 0.4107(10) 0.4181(8) 0.039(2) Uani 1 d . . . H14 H -0.3882 0.3296 0.4369 0.046 Uiso 1 calc R . . C15 C 0.0130(12) 0.1606(10) 0.2489(8) 0.031(2) Uani 1 d . . . C16 C 0.0372(11) 0.2428(10) 0.1923(7) 0.029(2) Uani 1 d . . . H16 H -0.0553 0.3089 0.1470 0.035 Uiso 1 calc R . . C17 C 0.1904(13) 0.2332(11) 0.1985(10) 0.045(3) Uani 1 d . . . H17 H 0.2028 0.2922 0.1588 0.054 Uiso 1 calc R . . C18 C 0.3233(13) 0.1374(12) 0.2628(9) 0.043(3) Uani 1 d . . . H18 H 0.4292 0.1292 0.2670 0.052 Uiso 1 calc R . . C19 C 0.3072(13) 0.0517(12) 0.3222(9) 0.045(3) Uani 1 d . . . H19 H 0.4004 -0.0135 0.3678 0.055 Uiso 1 calc R . . C20 C 0.1482(11) 0.0639(10) 0.3133(8) 0.036(2) Uani 1 d . . . H20 H 0.1347 0.0046 0.3521 0.043 Uiso 1 calc R . . Sn1A Sn 0.36459(6) -0.23338(6) -0.15536(5) 0.02900(16) Uani 1 d . . . I1A I 0.67350(6) -0.33222(6) -0.18875(5) 0.03629(17) Uani 1 d . . . C1A C 0.1590(12) -0.4001(9) 0.0115(9) 0.035(2) Uani 1 d . . . H1A H 0.1109 -0.4458 -0.0647 0.042 Uiso 1 calc R . . C2A C 0.0529(10) -0.2399(9) 0.0292(8) 0.028(2) Uani 1 d . . . H2A H -0.0600 -0.2123 -0.0238 0.034 Uiso 1 calc R . . C3A C 0.1570(9) -0.1626(9) 0.0227(7) 0.0240(18) Uani 1 d . . . H3C H 0.1360 -0.0642 0.0676 0.029 Uiso 1 calc R . . C4A C 0.3330(9) -0.2678(9) 0.0669(8) 0.027(2) Uani 1 d . . . H4A H 0.3713 -0.2559 0.1510 0.032 Uiso 1 calc R . . C5A C 0.4501(9) -0.2569(9) 0.0192(7) 0.0253(19) Uani 1 d . . . H5A1 H 0.5496 -0.3450 0.0317 0.030 Uiso 1 calc R . . H5A2 H 0.4819 -0.1730 0.0622 0.030 Uiso 1 calc R . . C6A C 0.0804(11) -0.3561(10) 0.1715(8) 0.033(2) Uani 1 d . . . C7A C 0.1929(14) -0.3741(12) 0.2911(10) 0.052(3) Uani 1 d . . . H7A1 H 0.3017 -0.3828 0.2944 0.077 Uiso 1 calc R . . H7A2 H 0.1998 -0.4617 0.3133 0.077 Uiso 1 calc R . . H7A3 H 0.1494 -0.2895 0.3426 0.077 Uiso 1 calc R . . C8A C -0.0821(11) -0.3612(11) 0.1558(9) 0.036(2) Uani 1 d . . . H8A1 H -0.1375 -0.2813 0.2052 0.054 Uiso 1 calc R . . H8A2 H -0.0673 -0.4537 0.1747 0.054 Uiso 1 calc R . . H8A3 H -0.1481 -0.3518 0.0773 0.054 Uiso 1 calc R . . O1A O 0.1600(8) -0.4656(6) 0.0951(6) 0.0389(17) Uani 1 d . . . O2A O 0.0614(7) -0.2209(6) 0.1466(5) 0.0290(14) Uani 1 d . . . O3A O 0.1251(7) -0.1580(6) -0.0944(5) 0.0294(14) Uani 1 d . . . H3A H 0.0310 -0.0984 -0.1191 0.044 Uiso 1 d R . . O4A O 0.3173(7) -0.4086(6) 0.0210(5) 0.0281(14) Uani 1 d . . . C9A C 0.2703(11) -0.0175(11) -0.1929(8) 0.036(2) Uani 1 d . . . C10A C 0.2621(12) 0.0127(13) -0.2923(8) 0.041(3) Uani 1 d . . . H10A H 0.3041 -0.0642 -0.3455 0.049 Uiso 1 calc R . . C11A C 0.1919(14) 0.1567(14) -0.3173(11) 0.056(3) Uani 1 d . . . H11A H 0.1824 0.1770 -0.3880 0.067 Uiso 1 calc R . . C12A C 0.1372(12) 0.2678(12) -0.2371(11) 0.050(3) Uani 1 d . . . H12A H 0.0928 0.3653 -0.2522 0.060 Uiso 1 calc R . . C13A C 0.1461(11) 0.2398(11) -0.1384(10) 0.041(2) Uani 1 d . . . H13A H 0.1039 0.3175 -0.0857 0.049 Uiso 1 calc R . . C14A C 0.2152(13) 0.1010(10) -0.1124(9) 0.038(2) Uani 1 d . . . H14A H 0.2265 0.0836 -0.0403 0.045 Uiso 1 calc R . . C15A C 0.2603(10) -0.3675(12) -0.2906(8) 0.041(3) Uani 1 d . . . C16A C 0.3414(12) -0.4941(11) -0.3393(9) 0.044(3) Uani 1 d . . . H16A H 0.4565 -0.5313 -0.3085 0.053 Uiso 1 calc R . . C17A C 0.2721(17) -0.5767(12) -0.4317(11) 0.059(3) Uani 1 d . . . H17A H 0.3380 -0.6676 -0.4612 0.071 Uiso 1 calc R . . C18A C 0.1044(17) -0.5237(16) -0.4803(12) 0.074(4) Uani 1 d . . . H18A H 0.0520 -0.5746 -0.5454 0.089 Uiso 1 calc R . . C19A C 0.024(2) -0.404(3) -0.4330(19) 0.196(15) Uani 1 d . . . H19A H -0.0907 -0.3679 -0.4636 0.235 Uiso 1 calc R . . C20A C 0.0915(16) -0.323(2) -0.3422(17) 0.178(13) Uani 1 d . . . H20A H 0.0223 -0.2344 -0.3127 0.214 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.0314(3) 0.0268(3) 0.0255(3) 0.0002(3) 0.0113(3) -0.0114(3) I1 0.0515(4) 0.0387(4) 0.0351(4) 0.0061(3) 0.0188(3) -0.0130(3) C1 0.039(5) 0.017(5) 0.029(5) -0.007(4) 0.017(4) -0.006(4) C2 0.038(5) 0.025(5) 0.017(4) -0.005(4) 0.011(4) -0.013(4) C3 0.021(5) 0.026(5) 0.024(5) 0.003(4) 0.001(4) -0.009(4) C4 0.011(4) 0.033(5) 0.021(5) 0.005(4) -0.006(3) -0.006(3) C5 0.036(6) 0.045(6) 0.038(6) -0.002(5) 0.015(4) -0.026(5) C6 0.050(6) 0.023(5) 0.033(6) -0.001(4) 0.027(5) -0.012(4) C7 0.059(7) 0.032(6) 0.034(6) -0.005(5) 0.017(5) -0.015(5) C8 0.057(7) 0.053(7) 0.033(6) -0.008(5) 0.024(5) -0.028(6) O1 0.034(4) 0.029(4) 0.023(3) 0.002(3) 0.009(3) 0.003(3) O2 0.022(3) 0.026(3) 0.021(3) -0.002(3) 0.004(2) -0.007(2) O3 0.032(3) 0.023(3) 0.027(3) 0.002(3) 0.010(3) 0.000(3) O4 0.028(3) 0.025(3) 0.025(3) 0.007(3) 0.009(3) -0.002(2) C9 0.030(5) 0.027(5) 0.027(5) 0.003(4) 0.004(4) -0.004(4) C10 0.031(5) 0.028(6) 0.048(7) 0.003(5) 0.010(5) -0.008(4) C11 0.033(5) 0.024(5) 0.042(6) -0.007(4) 0.005(4) -0.013(4) C12 0.048(6) 0.034(6) 0.029(6) -0.015(5) -0.001(5) -0.019(5) C13 0.060(7) 0.050(7) 0.035(6) -0.012(5) 0.024(5) -0.020(6) C14 0.051(6) 0.024(5) 0.035(6) 0.002(4) 0.017(5) -0.005(4) C15 0.045(6) 0.020(5) 0.029(5) 0.000(4) 0.017(4) -0.009(4) C16 0.032(5) 0.025(5) 0.027(5) -0.004(4) 0.008(4) -0.012(4) C17 0.056(7) 0.035(6) 0.059(7) -0.008(5) 0.036(6) -0.022(5) C18 0.041(6) 0.044(6) 0.046(7) -0.006(5) 0.014(5) -0.022(5) C19 0.043(6) 0.047(7) 0.037(6) -0.004(5) 0.005(5) -0.019(5) C20 0.044(6) 0.034(6) 0.035(6) -0.006(4) 0.014(5) -0.023(5) Sn1A 0.0261(3) 0.0287(4) 0.0269(3) -0.0015(3) 0.0074(3) -0.0081(3) I1A 0.0317(3) 0.0438(4) 0.0327(4) -0.0053(3) 0.0128(3) -0.0160(3) C1A 0.045(6) 0.012(5) 0.045(6) -0.002(4) 0.024(5) -0.002(4) C2A 0.025(5) 0.019(5) 0.033(5) 0.004(4) 0.012(4) 0.002(4) C3A 0.023(4) 0.022(4) 0.025(5) -0.002(4) 0.004(3) -0.011(3) C4A 0.014(4) 0.026(5) 0.034(5) 0.002(4) 0.001(4) -0.006(3) C5A 0.005(4) 0.030(5) 0.029(5) 0.003(4) -0.008(3) -0.006(3) C6A 0.035(5) 0.030(5) 0.039(6) 0.005(4) 0.010(4) -0.016(4) C7A 0.054(7) 0.043(7) 0.051(7) 0.006(5) 0.011(6) -0.015(5) C8A 0.037(6) 0.037(6) 0.042(6) 0.008(5) 0.007(4) -0.022(5) O1A 0.051(4) 0.017(3) 0.055(5) 0.004(3) 0.028(4) -0.008(3) O2A 0.035(3) 0.020(3) 0.038(4) 0.006(3) 0.016(3) -0.010(3) O3A 0.021(3) 0.021(3) 0.042(4) 0.007(3) 0.013(3) 0.002(2) O4A 0.034(3) 0.017(3) 0.038(4) 0.000(3) 0.018(3) -0.008(3) C9A 0.038(6) 0.036(6) 0.042(6) 0.003(5) 0.019(5) -0.016(4) C10A 0.032(5) 0.066(8) 0.031(6) 0.012(5) 0.001(4) -0.028(5) C11A 0.056(7) 0.068(9) 0.054(8) 0.025(7) 0.007(6) -0.029(6) C12A 0.031(6) 0.035(6) 0.082(10) 0.008(6) 0.005(6) -0.019(5) C13A 0.029(5) 0.039(6) 0.053(7) 0.006(5) 0.002(5) -0.019(4) C14A 0.060(7) 0.019(5) 0.040(6) -0.011(4) 0.028(5) -0.017(5) C15A 0.010(5) 0.057(7) 0.038(6) -0.009(5) -0.002(4) -0.012(4) C16A 0.032(6) 0.034(6) 0.052(7) -0.005(5) -0.007(5) -0.021(5) C17A 0.094(10) 0.026(6) 0.060(8) 0.000(6) 0.033(7) -0.019(6) C18A 0.070(10) 0.075(10) 0.058(9) -0.011(8) 0.008(7) -0.030(8) C19A 0.061(11) 0.18(2) 0.15(2) -0.106(17) -0.017(11) 0.031(12) C20A 0.020(8) 0.18(2) 0.161(19) -0.118(16) -0.009(9) 0.015(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. 'Linear' torsion angle excluded as per checkcif report I1A Sn1A O3A C3A 4.3(12) . . . . ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sn1 C15 2.135(9) . ? Sn1 C5 2.151(9) . ? Sn1 C9 2.153(9) . ? Sn1 I1 2.7630(8) . ? Sn1 O3 2.786(6) . ? C1 O4 1.401(11) . ? C1 O1 1.405(10) . ? C1 C2 1.551(12) . ? C1 H1 1.0000 . ? C2 O2 1.417(10) . ? C2 C3 1.506(12) . ? C2 H2 1.0000 . ? C3 O3 1.431(10) . ? C3 C4 1.532(12) . ? C3 H3B 1.0000 . ? C4 O4 1.459(10) . ? C4 C5 1.499(13) . ? C4 H4 1.0000 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O2 1.402(10) . ? C6 O1 1.456(11) . ? C6 C7 1.489(13) . ? C6 C8 1.524(13) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O3 H3 0.8400 . ? C9 C10 1.390(14) . ? C9 C14 1.395(13) . ? C10 C11 1.394(14) . ? C10 H10 0.9500 . ? C11 C12 1.371(15) . ? C11 H11 0.9500 . ? C12 C13 1.365(15) . ? C12 H12 0.9500 . ? C13 C14 1.382(14) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.376(13) . ? C15 C20 1.378(13) . ? C16 C17 1.382(13) . ? C16 H16 0.9500 . ? C17 C18 1.364(15) . ? C17 H17 0.9500 . ? C18 C19 1.387(15) . ? C18 H18 0.9500 . ? C19 C20 1.417(14) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? Sn1A C9A 2.124(10) . ? Sn1A C15A 2.125(9) . ? Sn1A C5A 2.134(8) . ? Sn1A O3A 2.418(6) . ? Sn1A I1A 2.8187(8) . ? C1A O1A 1.403(11) . ? C1A O4A 1.422(11) . ? C1A C2A 1.532(12) . ? C1A H1A 1.0000 . ? C2A O2A 1.449(10) . ? C2A C3A 1.532(12) . ? C2A H2A 1.0000 . ? C3A O3A 1.434(10) . ? C3A C4A 1.544(11) . ? C3A H3C 1.0000 . ? C4A O4A 1.456(10) . ? C4A C5A 1.499(12) . ? C4A H4A 1.0000 . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A O2A 1.425(10) . ? C6A O1A 1.432(11) . ? C6A C8A 1.495(12) . ? C6A C7A 1.525(14) . ? C7A H7A1 0.9800 . ? C7A H7A2 0.9800 . ? C7A H7A3 0.9800 . ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? O3A H3A 0.8400 . ? C9A C10A 1.362(13) . ? C9A C14A 1.423(13) . ? C10A C11A 1.412(16) . ? C10A H10A 0.9500 . ? C11A C12A 1.382(17) . ? C11A H11A 0.9500 . ? C12A C13A 1.340(15) . ? C12A H12A 0.9500 . ? C13A C14A 1.368(14) . ? C13A H13A 0.9500 . ? C14A H14A 0.9500 . ? C15A C16A 1.325(14) . ? C15A C20A 1.404(15) . ? C16A C17A 1.388(15) . ? C16A H16A 0.9500 . ? C17A C18A 1.390(18) . ? C17A H17A 0.9500 . ? C18A C19A 1.27(2) . ? C18A H18A 0.9500 . ? C19A C20A 1.36(2) . ? C19A H19A 0.9500 . ? C20A H20A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 Sn1 C5 118.8(4) . . ? C15 Sn1 C9 106.3(3) . . ? C5 Sn1 C9 125.5(4) . . ? C15 Sn1 I1 102.9(2) . . ? C5 Sn1 I1 96.8(3) . . ? C9 Sn1 I1 101.6(3) . . ? C15 Sn1 O3 97.4(3) . . ? C5 Sn1 O3 67.5(3) . . ? C9 Sn1 O3 78.3(3) . . ? I1 Sn1 O3 158.70(13) . . ? O4 C1 O1 110.5(7) . . ? O4 C1 C2 106.9(7) . . ? O1 C1 C2 104.6(7) . . ? O4 C1 H1 111.5 . . ? O1 C1 H1 111.5 . . ? C2 C1 H1 111.5 . . ? O2 C2 C3 108.4(7) . . ? O2 C2 C1 102.9(6) . . ? C3 C2 C1 104.5(7) . . ? O2 C2 H2 113.4 . . ? C3 C2 H2 113.4 . . ? C1 C2 H2 113.4 . . ? O3 C3 C2 108.8(7) . . ? O3 C3 C4 105.7(7) . . ? C2 C3 C4 101.5(7) . . ? O3 C3 H3B 113.3 . . ? C2 C3 H3B 113.3 . . ? C4 C3 H3B 113.3 . . ? O4 C4 C5 108.6(6) . . ? O4 C4 C3 103.3(7) . . ? C5 C4 C3 116.9(8) . . ? O4 C4 H4 109.2 . . ? C5 C4 H4 109.2 . . ? C3 C4 H4 109.2 . . ? C4 C5 Sn1 111.0(6) . . ? C4 C5 H5A 109.4 . . ? Sn1 C5 H5A 109.4 . . ? C4 C5 H5B 109.4 . . ? Sn1 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? O2 C6 O1 103.3(7) . . ? O2 C6 C7 109.9(8) . . ? O1 C6 C7 107.9(8) . . ? O2 C6 C8 111.9(7) . . ? O1 C6 C8 108.3(8) . . ? C7 C6 C8 114.8(8) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 O1 C6 109.2(6) . . ? C6 O2 C2 108.4(6) . . ? C3 O3 Sn1 109.9(5) . . ? C3 O3 H3 109.5 . . ? Sn1 O3 H3 122.0 . . ? C1 O4 C4 108.5(6) . . ? C10 C9 C14 119.7(9) . . ? C10 C9 Sn1 118.7(7) . . ? C14 C9 Sn1 121.1(7) . . ? C9 C10 C11 118.8(10) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C12 C11 C10 121.3(10) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C13 C12 C11 119.4(9) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 121.1(10) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C9 119.7(10) . . ? C13 C14 H14 120.2 . . ? C9 C14 H14 120.2 . . ? C16 C15 C20 118.0(9) . . ? C16 C15 Sn1 121.0(7) . . ? C20 C15 Sn1 121.0(7) . . ? C15 C16 C17 122.8(9) . . ? C15 C16 H16 118.6 . . ? C17 C16 H16 118.6 . . ? C18 C17 C16 118.6(10) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C17 C18 C19 121.4(10) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C20 118.4(10) . . ? C18 C19 H19 120.8 . . ? C20 C19 H19 120.8 . . ? C15 C20 C19 120.8(9) . . ? C15 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C9A Sn1A C15A 111.1(4) . . ? C9A Sn1A C5A 115.6(4) . . ? C15A Sn1A C5A 126.9(4) . . ? C9A Sn1A O3A 84.8(3) . . ? C15A Sn1A O3A 87.1(3) . . ? C5A Sn1A O3A 73.6(3) . . ? C9A Sn1A I1A 100.3(2) . . ? C15A Sn1A I1A 98.7(2) . . ? C5A Sn1A I1A 96.7(2) . . ? O3A Sn1A I1A 170.25(15) . . ? O1A C1A O4A 112.3(8) . . ? O1A C1A C2A 106.3(7) . . ? O4A C1A C2A 108.2(7) . . ? O1A C1A H1A 110.0 . . ? O4A C1A H1A 110.0 . . ? C2A C1A H1A 110.0 . . ? O2A C2A C1A 101.6(7) . . ? O2A C2A C3A 106.6(7) . . ? C1A C2A C3A 102.6(7) . . ? O2A C2A H2A 114.8 . . ? C1A C2A H2A 114.8 . . ? C3A C2A H2A 114.8 . . ? O3A C3A C2A 106.7(6) . . ? O3A C3A C4A 108.3(7) . . ? C2A C3A C4A 103.4(7) . . ? O3A C3A H3C 112.6 . . ? C2A C3A H3C 112.6 . . ? C4A C3A H3C 112.6 . . ? O4A C4A C5A 107.1(7) . . ? O4A C4A C3A 102.2(6) . . ? C5A C4A C3A 113.0(7) . . ? O4A C4A H4A 111.4 . . ? C5A C4A H4A 111.4 . . ? C3A C4A H4A 111.4 . . ? C4A C5A Sn1A 116.3(5) . . ? C4A C5A H5A1 108.2 . . ? Sn1A C5A H5A1 108.2 . . ? C4A C5A H5A2 108.2 . . ? Sn1A C5A H5A2 108.2 . . ? H5A1 C5A H5A2 107.4 . . ? O2A C6A O1A 106.1(7) . . ? O2A C6A C8A 110.3(7) . . ? O1A C6A C8A 110.9(8) . . ? O2A C6A C7A 107.6(8) . . ? O1A C6A C7A 108.8(8) . . ? C8A C6A C7A 112.8(9) . . ? C6A C7A H7A1 109.5 . . ? C6A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C6A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C6A C8A H8A1 109.5 . . ? C6A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C6A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C1A O1A C6A 109.3(6) . . ? C6A O2A C2A 107.4(6) . . ? C3A O3A Sn1A 115.1(4) . . ? C3A O3A H3A 109.5 . . ? Sn1A O3A H3A 129.8 . . ? C1A O4A C4A 109.8(6) . . ? C10A C9A C14A 118.0(9) . . ? C10A C9A Sn1A 121.9(8) . . ? C14A C9A Sn1A 120.1(7) . . ? C9A C10A C11A 120.8(11) . . ? C9A C10A H10A 119.6 . . ? C11A C10A H10A 119.6 . . ? C12A C11A C10A 118.9(11) . . ? C12A C11A H11A 120.6 . . ? C10A C11A H11A 120.6 . . ? C13A C12A C11A 120.9(11) . . ? C13A C12A H12A 119.5 . . ? C11A C12A H12A 119.5 . . ? C12A C13A C14A 120.9(10) . . ? C12A C13A H13A 119.5 . . ? C14A C13A H13A 119.5 . . ? C13A C14A C9A 120.3(10) . . ? C13A C14A H14A 119.8 . . ? C9A C14A H14A 119.8 . . ? C16A C15A C20A 112.6(10) . . ? C16A C15A Sn1A 126.1(7) . . ? C20A C15A Sn1A 121.2(9) . . ? C15A C16A C17A 125.4(10) . . ? C15A C16A H16A 117.3 . . ? C17A C16A H16A 117.3 . . ? C16A C17A C18A 118.7(12) . . ? C16A C17A H17A 120.6 . . ? C18A C17A H17A 120.6 . . ? C19A C18A C17A 116.6(14) . . ? C19A C18A H18A 121.7 . . ? C17A C18A H18A 121.7 . . ? C18A C19A C20A 124.9(16) . . ? C18A C19A H19A 117.6 . . ? C20A C19A H19A 117.6 . . ? C19A C20A C15A 121.8(14) . . ? C19A C20A H20A 119.1 . . ? C15A C20A H20A 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C1 C2 O2 -104.5(7) . . . . ? O1 C1 C2 O2 12.8(9) . . . . ? O4 C1 C2 C3 8.7(9) . . . . ? O1 C1 C2 C3 126.0(7) . . . . ? O2 C2 C3 O3 -168.2(6) . . . . ? C1 C2 C3 O3 82.5(8) . . . . ? O2 C2 C3 C4 80.6(8) . . . . ? C1 C2 C3 C4 -28.6(8) . . . . ? O3 C3 C4 O4 -74.9(7) . . . . ? C2 C3 C4 O4 38.6(8) . . . . ? O3 C3 C4 C5 44.4(9) . . . . ? C2 C3 C4 C5 157.9(7) . . . . ? O4 C4 C5 Sn1 49.5(8) . . . . ? C3 C4 C5 Sn1 -66.9(8) . . . . ? C15 Sn1 C5 C4 -47.5(8) . . . . ? C9 Sn1 C5 C4 94.2(7) . . . . ? I1 Sn1 C5 C4 -156.3(6) . . . . ? O3 Sn1 C5 C4 38.6(6) . . . . ? O4 C1 O1 C6 122.7(7) . . . . ? C2 C1 O1 C6 8.0(9) . . . . ? O2 C6 O1 C1 -26.2(9) . . . . ? C7 C6 O1 C1 -142.6(8) . . . . ? C8 C6 O1 C1 92.6(8) . . . . ? O1 C6 O2 C2 35.3(8) . . . . ? C7 C6 O2 C2 150.2(8) . . . . ? C8 C6 O2 C2 -81.0(9) . . . . ? C3 C2 O2 C6 -140.4(7) . . . . ? C1 C2 O2 C6 -30.1(8) . . . . ? C2 C3 O3 Sn1 -116.0(6) . . . . ? C4 C3 O3 Sn1 -7.6(7) . . . . ? C15 Sn1 O3 C3 100.2(5) . . . . ? C5 Sn1 O3 C3 -17.9(5) . . . . ? C9 Sn1 O3 C3 -154.6(6) . . . . ? I1 Sn1 O3 C3 -62.5(6) . . . . ? O1 C1 O4 C4 -96.7(8) . . . . ? C2 C1 O4 C4 16.5(9) . . . . ? C5 C4 O4 C1 -159.9(7) . . . . ? C3 C4 O4 C1 -35.0(8) . . . . ? C15 Sn1 C9 C10 49.6(8) . . . . ? C5 Sn1 C9 C10 -96.0(8) . . . . ? I1 Sn1 C9 C10 156.9(7) . . . . ? O3 Sn1 C9 C10 -44.8(7) . . . . ? C15 Sn1 C9 C14 -122.2(8) . . . . ? C5 Sn1 C9 C14 92.3(8) . . . . ? I1 Sn1 C9 C14 -14.8(8) . . . . ? O3 Sn1 C9 C14 143.4(8) . . . . ? C14 C9 C10 C11 -2.5(14) . . . . ? Sn1 C9 C10 C11 -174.4(7) . . . . ? C9 C10 C11 C12 3.2(14) . . . . ? C10 C11 C12 C13 -1.9(15) . . . . ? C11 C12 C13 C14 -0.2(16) . . . . ? C12 C13 C14 C9 0.8(16) . . . . ? C10 C9 C14 C13 0.6(15) . . . . ? Sn1 C9 C14 C13 172.3(8) . . . . ? C5 Sn1 C15 C16 79.6(8) . . . . ? C9 Sn1 C15 C16 -68.7(8) . . . . ? I1 Sn1 C15 C16 -175.1(7) . . . . ? O3 Sn1 C15 C16 11.3(8) . . . . ? C5 Sn1 C15 C20 -101.2(8) . . . . ? C9 Sn1 C15 C20 110.6(8) . . . . ? I1 Sn1 C15 C20 4.2(8) . . . . ? O3 Sn1 C15 C20 -169.5(7) . . . . ? C20 C15 C16 C17 -0.8(14) . . . . ? Sn1 C15 C16 C17 178.5(7) . . . . ? C15 C16 C17 C18 0.5(14) . . . . ? C16 C17 C18 C19 -0.7(15) . . . . ? C17 C18 C19 C20 1.1(15) . . . . ? C16 C15 C20 C19 1.2(14) . . . . ? Sn1 C15 C20 C19 -178.1(7) . . . . ? C18 C19 C20 C15 -1.3(15) . . . . ? O1A C1A C2A O2A 22.9(9) . . . . ? O4A C1A C2A O2A -97.9(8) . . . . ? O1A C1A C2A C3A 133.1(7) . . . . ? O4A C1A C2A C3A 12.3(9) . . . . ? O2A C2A C3A O3A -169.6(6) . . . . ? C1A C2A C3A O3A 84.1(8) . . . . ? O2A C2A C3A C4A 76.3(7) . . . . ? C1A C2A C3A C4A -30.0(9) . . . . ? O3A C3A C4A O4A -75.8(7) . . . . ? C2A C3A C4A O4A 37.2(8) . . . . ? O3A C3A C4A C5A 39.0(9) . . . . ? C2A C3A C4A C5A 152.0(7) . . . . ? O4A C4A C5A Sn1A 70.9(7) . . . . ? C3A C4A C5A Sn1A -40.9(9) . . . . ? C9A Sn1A C5A C4A 96.5(7) . . . . ? C15A Sn1A C5A C4A -52.6(8) . . . . ? O3A Sn1A C5A C4A 20.8(6) . . . . ? I1A Sn1A C5A C4A -158.8(6) . . . . ? O4A C1A O1A C6A 111.0(8) . . . . ? C2A C1A O1A C6A -7.2(10) . . . . ? O2A C6A O1A C1A -11.9(9) . . . . ? C8A C6A O1A C1A 107.9(9) . . . . ? C7A C6A O1A C1A -127.5(8) . . . . ? O1A C6A O2A C2A 27.5(9) . . . . ? C8A C6A O2A C2A -92.7(8) . . . . ? C7A C6A O2A C2A 143.8(8) . . . . ? C1A C2A O2A C6A -30.6(8) . . . . ? C3A C2A O2A C6A -137.6(7) . . . . ? C2A C3A O3A Sn1A -132.1(5) . . . . ? C4A C3A O3A Sn1A -21.4(7) . . . . ? C9A Sn1A O3A C3A -117.2(6) . . . . ? C15A Sn1A O3A C3A 131.4(6) . . . . ? C5A Sn1A O3A C3A 1.4(5) . . . . ? O1A C1A O4A C4A -105.2(8) . . . . ? C2A C1A O4A C4A 11.9(10) . . . . ? C5A C4A O4A C1A -149.6(7) . . . . ? C3A C4A O4A C1A -30.7(9) . . . . ? C15A Sn1A C9A C10A -48.4(8) . . . . ? C5A Sn1A C9A C10A 157.7(7) . . . . ? O3A Sn1A C9A C10A -133.3(8) . . . . ? I1A Sn1A C9A C10A 55.2(8) . . . . ? C15A Sn1A C9A C14A 132.5(8) . . . . ? C5A Sn1A C9A C14A -21.4(9) . . . . ? O3A Sn1A C9A C14A 47.6(7) . . . . ? I1A Sn1A C9A C14A -124.0(7) . . . . ? C14A C9A C10A C11A -3.8(14) . . . . ? Sn1A C9A C10A C11A 177.0(7) . . . . ? C9A C10A C11A C12A 2.6(15) . . . . ? C10A C11A C12A C13A -1.8(16) . . . . ? C11A C12A C13A C14A 2.5(15) . . . . ? C12A C13A C14A C9A -3.8(15) . . . . ? C10A C9A C14A C13A 4.4(14) . . . . ? Sn1A C9A C14A C13A -176.4(7) . . . . ? C9A Sn1A C15A C16A 128.7(10) . . . . ? C5A Sn1A C15A C16A -81.0(11) . . . . ? O3A Sn1A C15A C16A -148.0(10) . . . . ? I1A Sn1A C15A C16A 24.1(11) . . . . ? C9A Sn1A C15A C20A -47.6(17) . . . . ? C5A Sn1A C15A C20A 102.6(16) . . . . ? O3A Sn1A C15A C20A 35.7(16) . . . . ? I1A Sn1A C15A C20A -152.2(16) . . . . ? C20A C15A C16A C17A 0(2) . . . . ? Sn1A C15A C16A C17A -176.2(9) . . . . ? C15A C16A C17A C18A 1.3(19) . . . . ? C16A C17A C18A C19A -3(3) . . . . ? C17A C18A C19A C20A 2(4) . . . . ? C18A C19A C20A C15A 0(5) . . . . ? C16A C15A C20A C19A -1(4) . . . . ? Sn1A C15A C20A C19A 176(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O4A 0.84 1.97 2.773(8) 160.1 1_465 O3A H3A O1 0.84 1.89 2.718(8) 169.3 . _diffrn_measured_fraction_theta_max 0.818 _diffrn_reflns_theta_full 30.82 _diffrn_measured_fraction_theta_full 0.818 _refine_diff_density_max 0.859 _refine_diff_density_min -1.315 _refine_diff_density_rms 0.159 #===END data_(D)-5 _database_code_CSD 185951 # _publ_requested_journal test _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-deoxy-5-C-diiodophenylstannyl-1,2-O-isopropylidene-alpha-D- xylofuranose chloroform solvate ; _chemical_name_common ? _chemical_formula_moiety 'C14 H18 I2 O4 Sn, 0.5(C H Cl3)' _chemical_formula_sum 'C14.50 H18.50 Cl1.50 I2 O4 Sn' _chemical_formula_weight 682.46 _chemical_melting_point '429-431 (dec)' _chemical_absolute_configuration rmad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 23.904(9) _cell_length_b 10.824(4) _cell_length_c 7.954(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2058.0(19) _cell_formula_units_Z 4 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 8938 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 25.08 _exptl_crystal_preparation 'from CHCl3 as solvent' _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1276 _exptl_absorpt_coefficient_mu 4.450 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details 'DIFABS; Walker and Stuart, 1983)' _exptl_absorpt_correction_T_min 0.3487 _exptl_absorpt_correction_T_max 0.4698 _exptl_special_details ; General cell determination and refinement and data collection strategy given by Darr et al, (1993). [Darr, J.A, Drake, S.R., Hursthouse, M.B. & Malik, K.M.A. (1993). Inorg. Chem. 32, 5704-5708.] ; _diffrn_ambient_temperature 108(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Delft Instruments FAST area detector' _diffrn_measurement_method 'phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8938 _diffrn_reflns_av_R_equivalents 0.1013 _diffrn_reflns_av_sigmaI/netI 0.0742 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.08 _reflns_number_total 3226 _reflns_number_gt 3088 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'MADNES software (Pflugrath & Messerschmidt, 1989)' _computing_cell_refinement 'MADNES software (Pflugrath & Messerschmidt, 1989)' _computing_data_reduction 'ABSMAD (Karaulov, 1992)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-H except C of solvate CHCl3 refined anisotropically. H in calculated positions and refined with a riding model. Absolute structure from 1296 Friedel pairs. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(5) _refine_ls_number_reflns 3226 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.15593(2) 0.21679(4) -0.10601(7) 0.02625(16) Uani 1 d . . . I2 I 0.10230(2) 0.57453(4) -0.11570(6) 0.02745(16) Uani 1 d . . . Sn1 Sn 0.14622(2) 0.40795(4) 0.11504(7) 0.02038(16) Uani 1 d . . . O4 O 0.2260(2) 0.5145(5) 0.4460(6) 0.0225(12) Uani 1 d . . . O1 O 0.2876(3) 0.5160(5) 0.6725(7) 0.0316(14) Uani 1 d . . . O2 O 0.3305(2) 0.3523(5) 0.5504(7) 0.0285(14) Uani 1 d . . . O3 O 0.2056(2) 0.2741(5) 0.3119(7) 0.0267(12) Uani 1 d . . . H3 H 0.2079 0.1968 0.3184 0.040 Uiso 1 d R . . C1 C 0.2442(3) 0.4507(6) 0.5908(11) 0.0245(18) Uani 1 d . . . H1 H 0.2125 0.4331 0.6690 0.029 Uiso 1 calc R . . C2 C 0.2726(3) 0.3289(7) 0.5282(11) 0.0214(17) Uani 1 d . . . H2 H 0.2593 0.2536 0.5891 0.026 Uiso 1 calc R . . C3 C 0.2591(3) 0.3270(7) 0.3403(10) 0.0245(18) Uani 1 d . . . H3A H 0.2890 0.2854 0.2731 0.029 Uiso 1 calc R . . C4 C 0.2558(4) 0.4648(7) 0.3042(11) 0.0263(18) Uani 1 d . . . H4 H 0.2943 0.5005 0.3002 0.032 Uiso 1 calc R . . C5 C 0.2244(4) 0.4999(8) 0.1474(11) 0.032(2) Uani 1 d . . . H5A H 0.2483 0.4819 0.0488 0.038 Uiso 1 calc R . . H5B H 0.2176 0.5901 0.1493 0.038 Uiso 1 calc R . . C6 C 0.3379(4) 0.4394(8) 0.6818(11) 0.0281(19) Uani 1 d . . . C7 C 0.3874(4) 0.5164(8) 0.6501(13) 0.040(2) Uani 1 d . . . H7A H 0.4199 0.4632 0.6301 0.061 Uiso 1 calc R . . H7B H 0.3945 0.5690 0.7480 0.061 Uiso 1 calc R . . H7C H 0.3808 0.5682 0.5511 0.061 Uiso 1 calc R . . C8 C 0.3378(4) 0.3759(8) 0.8524(12) 0.039(2) Uani 1 d . . . H8A H 0.3063 0.3180 0.8584 0.058 Uiso 1 calc R . . H8B H 0.3340 0.4381 0.9413 0.058 Uiso 1 calc R . . H8C H 0.3729 0.3307 0.8674 0.058 Uiso 1 calc R . . C9 C 0.0770(3) 0.3669(7) 0.2752(10) 0.0234(18) Uani 1 d . . . C10 C 0.0832(4) 0.3590(9) 0.4489(11) 0.038(2) Uani 1 d . . . H10 H 0.1185 0.3726 0.5004 0.046 Uiso 1 calc R . . C11 C 0.0360(4) 0.3306(10) 0.5459(14) 0.042(3) Uani 1 d . . . H11 H 0.0400 0.3238 0.6644 0.050 Uiso 1 calc R . . C12 C -0.0157(4) 0.3125(9) 0.4758(12) 0.037(2) Uani 1 d . . . H12 H -0.0472 0.2937 0.5440 0.044 Uiso 1 calc R . . C13 C -0.0208(4) 0.3222(11) 0.3049(13) 0.044(3) Uani 1 d . . . H13 H -0.0563 0.3118 0.2534 0.053 Uiso 1 calc R . . C14 C 0.0275(4) 0.3482(11) 0.2030(12) 0.049(3) Uani 1 d . . . H14 H 0.0241 0.3520 0.0841 0.059 Uiso 1 calc R . . Cl1 Cl 0.5506(5) 0.5390(9) 0.2763(12) 0.104(4) Uani 0.50 d P A -1 Cl2 Cl 0.5025(3) 0.5819(10) -0.0423(8) 0.099(3) Uani 0.50 d P A -1 Cl3 Cl 0.4528(4) 0.4050(9) 0.1755(17) 0.113(4) Uani 0.50 d P A -1 C15 C 0.5166(11) 0.473(3) 0.139(3) 0.070(7) Uiso 0.50 d P A -1 H15 H 0.5414 0.4067 0.0937 0.084 Uiso 0.50 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0326(3) 0.0182(3) 0.0279(3) -0.0036(2) 0.0005(2) 0.0031(2) I2 0.0372(3) 0.0212(3) 0.0239(3) 0.0025(2) -0.0047(2) 0.0059(2) Sn1 0.0244(3) 0.0147(3) 0.0221(3) 0.0007(2) -0.0039(2) -0.00063(19) O4 0.024(3) 0.016(3) 0.027(3) 0.003(2) -0.008(2) 0.003(2) O1 0.036(3) 0.022(3) 0.036(3) -0.007(2) -0.014(3) 0.005(3) O2 0.021(3) 0.025(3) 0.040(3) -0.003(2) -0.009(2) 0.006(2) O3 0.031(3) 0.010(3) 0.039(3) -0.003(2) -0.010(3) -0.002(2) C1 0.035(5) 0.009(4) 0.029(5) -0.004(3) -0.009(4) 0.002(3) C2 0.022(4) 0.010(4) 0.032(5) 0.000(3) -0.004(3) 0.002(3) C3 0.026(4) 0.017(4) 0.030(5) -0.005(3) -0.006(3) -0.002(3) C4 0.027(4) 0.011(4) 0.041(5) 0.001(3) 0.000(4) -0.010(3) C5 0.025(4) 0.016(4) 0.054(6) 0.008(4) -0.007(4) -0.007(3) C6 0.025(4) 0.017(4) 0.042(5) -0.008(3) -0.015(4) 0.007(3) C7 0.041(5) 0.017(4) 0.064(6) -0.001(4) -0.021(5) 0.001(4) C8 0.050(6) 0.013(4) 0.053(6) -0.003(4) -0.028(5) 0.011(4) C9 0.022(4) 0.009(4) 0.039(5) 0.006(3) 0.004(3) 0.006(3) C10 0.037(5) 0.050(6) 0.029(5) -0.007(4) -0.002(4) -0.005(5) C11 0.039(6) 0.058(7) 0.028(5) -0.010(4) -0.001(4) -0.005(5) C12 0.037(5) 0.027(5) 0.046(6) 0.006(4) 0.013(4) -0.002(4) C13 0.025(5) 0.071(7) 0.036(6) 0.021(5) -0.007(4) 0.002(5) C14 0.040(6) 0.088(9) 0.019(5) 0.015(5) -0.002(4) -0.008(5) Cl1 0.138(8) 0.074(6) 0.100(7) -0.050(5) -0.079(7) 0.045(6) Cl2 0.055(3) 0.185(9) 0.058(3) 0.043(5) 0.005(3) 0.004(6) Cl3 0.092(6) 0.075(7) 0.172(11) 0.076(7) -0.038(7) -0.020(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Sn1 2.7251(13) . ? I2 Sn1 2.7789(12) . ? Sn1 C5 2.132(8) . ? Sn1 C9 2.134(8) . ? Sn1 O3 2.562(6) . ? O4 C1 1.412(9) . ? O4 C4 1.438(10) . ? O1 C1 1.413(10) . ? O1 C6 1.461(10) . ? O2 C6 1.419(10) . ? O2 C2 1.419(10) . ? O3 C3 1.419(10) . ? O3 H3 0.8400 . ? C1 C2 1.564(11) . ? C1 H1 1.0000 . ? C2 C3 1.529(12) . ? C2 H2 1.0000 . ? C3 C4 1.522(11) . ? C3 H3A 1.0000 . ? C4 C5 1.504(12) . ? C4 H4 1.0000 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.470(13) . ? C6 C8 1.521(13) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.332(13) . ? C9 C10 1.392(13) . ? C10 C11 1.400(14) . ? C10 H10 0.9500 . ? C11 C12 1.371(15) . ? C11 H11 0.9500 . ? C12 C13 1.369(14) . ? C12 H12 0.9500 . ? C13 C14 1.438(13) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? Cl1 C15 1.54(3) . ? Cl2 C15 1.89(2) . ? Cl3 C15 1.72(3) . ? C15 H15 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Sn1 C9 134.7(3) . . ? C5 Sn1 O3 72.8(3) . . ? C9 Sn1 O3 87.0(2) . . ? C5 Sn1 I1 111.0(3) . . ? C9 Sn1 I1 107.1(2) . . ? O3 Sn1 I1 85.29(13) . . ? C5 Sn1 I2 96.2(2) . . ? C9 Sn1 I2 103.7(2) . . ? O3 Sn1 I2 168.45(13) . . ? I1 Sn1 I2 95.67(5) . . ? C1 O4 C4 107.7(6) . . ? C1 O1 C6 110.1(6) . . ? C6 O2 C2 109.4(6) . . ? C3 O3 Sn1 111.6(4) . . ? C3 O3 H3 109.5 . . ? Sn1 O3 H3 129.5 . . ? O4 C1 O1 110.9(6) . . ? O4 C1 C2 106.7(6) . . ? O1 C1 C2 104.5(6) . . ? O4 C1 H1 111.5 . . ? O1 C1 H1 111.5 . . ? C2 C1 H1 111.5 . . ? O2 C2 C3 109.3(7) . . ? O2 C2 C1 103.4(6) . . ? C3 C2 C1 103.4(6) . . ? O2 C2 H2 113.3 . . ? C3 C2 H2 113.3 . . ? C1 C2 H2 113.3 . . ? O3 C3 C4 108.6(7) . . ? O3 C3 C2 110.5(7) . . ? C4 C3 C2 100.5(6) . . ? O3 C3 H3A 112.2 . . ? C4 C3 H3A 112.2 . . ? C2 C3 H3A 112.2 . . ? O4 C4 C5 108.0(7) . . ? O4 C4 C3 104.2(6) . . ? C5 C4 C3 115.5(7) . . ? O4 C4 H4 109.7 . . ? C5 C4 H4 109.7 . . ? C3 C4 H4 109.7 . . ? C4 C5 Sn1 114.8(5) . . ? C4 C5 H5A 108.6 . . ? Sn1 C5 H5A 108.6 . . ? C4 C5 H5B 108.6 . . ? Sn1 C5 H5B 108.6 . . ? H5A C5 H5B 107.5 . . ? O2 C6 O1 103.8(6) . . ? O2 C6 C7 110.5(8) . . ? O1 C6 C7 109.4(7) . . ? O2 C6 C8 110.9(7) . . ? O1 C6 C8 107.5(7) . . ? C7 C6 C8 114.2(7) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 120.8(9) . . ? C14 C9 Sn1 117.6(6) . . ? C10 C9 Sn1 121.6(7) . . ? C9 C10 C11 118.4(9) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C12 C11 C10 122.3(9) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C13 C12 C11 118.2(9) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? C12 C13 C14 120.3(9) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C9 C14 C13 120.0(8) . . ? C9 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? Cl1 C15 Cl3 123.4(18) . . ? Cl1 C15 Cl2 110.3(16) . . ? Cl3 C15 Cl2 103.7(13) . . ? Cl1 C15 H15 106.1 . . ? Cl3 C15 H15 106.1 . . ? Cl2 C15 H15 106.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 Sn1 O3 C3 -0.6(5) . . . . ? C9 Sn1 O3 C3 -139.6(5) . . . . ? I1 Sn1 O3 C3 113.0(5) . . . . ? I2 Sn1 O3 C3 17.8(9) . . . . ? C4 O4 C1 O1 94.9(7) . . . . ? C4 O4 C1 C2 -18.3(8) . . . . ? C6 O1 C1 O4 -120.9(7) . . . . ? C6 O1 C1 C2 -6.3(8) . . . . ? C6 O2 C2 C3 136.5(7) . . . . ? C6 O2 C2 C1 26.9(8) . . . . ? O4 C1 C2 O2 105.5(7) . . . . ? O1 C1 C2 O2 -12.0(8) . . . . ? O4 C1 C2 C3 -8.4(8) . . . . ? O1 C1 C2 C3 -125.9(7) . . . . ? Sn1 O3 C3 C4 22.2(8) . . . . ? Sn1 O3 C3 C2 131.5(5) . . . . ? O2 C2 C3 O3 165.5(6) . . . . ? C1 C2 C3 O3 -84.9(7) . . . . ? O2 C2 C3 C4 -80.0(8) . . . . ? C1 C2 C3 C4 29.6(8) . . . . ? C1 O4 C4 C5 161.6(6) . . . . ? C1 O4 C4 C3 38.4(8) . . . . ? O3 C3 C4 O4 74.3(7) . . . . ? C2 C3 C4 O4 -41.7(8) . . . . ? O3 C3 C4 C5 -43.9(10) . . . . ? C2 C3 C4 C5 -159.9(7) . . . . ? O4 C4 C5 Sn1 -70.1(7) . . . . ? C3 C4 C5 Sn1 46.0(10) . . . . ? C9 Sn1 C5 C4 45.0(8) . . . . ? O3 Sn1 C5 C4 -22.4(6) . . . . ? I1 Sn1 C5 C4 -100.2(6) . . . . ? I2 Sn1 C5 C4 161.3(6) . . . . ? C2 O2 C6 O1 -30.9(8) . . . . ? C2 O2 C6 C7 -148.1(7) . . . . ? C2 O2 C6 C8 84.2(8) . . . . ? C1 O1 C6 O2 22.4(9) . . . . ? C1 O1 C6 C7 140.3(7) . . . . ? C1 O1 C6 C8 -95.1(7) . . . . ? C5 Sn1 C9 C14 156.2(7) . . . . ? O3 Sn1 C9 C14 -141.7(8) . . . . ? I1 Sn1 C9 C14 -57.6(8) . . . . ? I2 Sn1 C9 C14 42.8(8) . . . . ? C5 Sn1 C9 C10 -24.2(9) . . . . ? O3 Sn1 C9 C10 37.8(7) . . . . ? I1 Sn1 C9 C10 122.0(7) . . . . ? I2 Sn1 C9 C10 -137.6(7) . . . . ? C14 C9 C10 C11 0.1(15) . . . . ? Sn1 C9 C10 C11 -179.4(7) . . . . ? C9 C10 C11 C12 -1.0(16) . . . . ? C10 C11 C12 C13 0.3(17) . . . . ? C11 C12 C13 C14 1.3(18) . . . . ? C10 C9 C14 C13 1.4(16) . . . . ? Sn1 C9 C14 C13 -179.0(9) . . . . ? C12 C13 C14 C9 -2.2(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O1 0.84 1.96 2.802(8) 178.5 4_546 C4 H4 I1 1.00 3.05 3.791(8) 132.3 4 C15 H15 I1 1.00 3.05 3.92(2) 146.7 3 _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.912 _refine_diff_density_max 2.444 _refine_diff_density_min -1.093 _refine_diff_density_rms 0.220 #===END data_(L)-5 _database_code_CSD 185952 _publ_requested_journal test _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-deoxy-5-C-(diiodophenylstannyl)-1,2-O-isopropylidene-alpha-L- xylofuranose chloroform solvate ; _chemical_name_common ? _chemical_formula_moiety 'C14 H18 I2 O4 Sn, 0.5(C H Cl3)' _chemical_formula_sum 'C14.50 H18.50 Cl1.50 I2 O4 Sn' _chemical_formula_weight 682.46 _chemical_melting_point '429-431 (dec)' _chemical_absolute_configuration rmad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 24.2808(15) _cell_length_b 10.8472(7) _cell_length_c 8.0682(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2125.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used 4158 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 24.00 _exptl_crystal_preparation 'from CHCl3 as solvent' _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1276 _exptl_absorpt_coefficient_mu 4.310 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1999)' # Compare next 2 with SHELXL calc. 0.2218 and 0.3060 _exptl_absorpt_correction_T_min 0.624 _exptl_absorpt_correction_T_max 0.928 _exptl_special_details ; ? ; _diffrn_ambient_temperature 301(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11487 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 24.01 _reflns_number_total 3361 _reflns_number_gt 3243 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-H refined anisotropically. H in calculated positions and refined with a riding model. Absolute structure from 1407 Friedel pairs. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0279P)^2^+1.5040P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_number_reflns 3361 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0251 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0570 _refine_ls_wR_factor_gt 0.0565 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.843608(16) 0.78165(3) 1.10523(5) 0.06481(11) Uani 1 d . . . I2 I 0.895047(18) 0.42326(4) 1.11177(5) 0.07030(12) Uani 1 d . . . Sn1 Sn 0.852513(13) 0.59180(3) 0.88814(5) 0.04715(9) Uani 1 d . . . O4 O 0.77286(15) 0.4880(3) 0.5609(5) 0.0553(10) Uani 1 d . . . O1 O 0.71218(16) 0.4857(3) 0.3372(5) 0.0620(11) Uani 1 d . . . O2 O 0.67071(15) 0.6500(3) 0.4582(5) 0.0603(10) Uani 1 d . . . O3 O 0.79370(14) 0.7271(3) 0.6919(5) 0.0576(9) Uani 1 d . . . H3 H 0.7920 0.8023 0.6837 0.086 Uiso 1 d R . . C1 C 0.7553(2) 0.5510(4) 0.4187(7) 0.0484(12) Uani 1 d . . . H1 H 0.7861 0.5673 0.3434 0.058 Uiso 1 calc R . . C2 C 0.7283(2) 0.6718(5) 0.4784(7) 0.0490(12) Uani 1 d . . . H2 H 0.7415 0.7451 0.4195 0.059 Uiso 1 calc R . . C3 C 0.7399(2) 0.6747(5) 0.6630(7) 0.0490(13) Uani 1 d . . . H3A H 0.7108 0.7157 0.7266 0.059 Uiso 1 calc R . . C4 C 0.7447(2) 0.5372(5) 0.7022(7) 0.0531(13) Uani 1 d . . . H4 H 0.7076 0.5016 0.7070 0.064 Uiso 1 calc R . . C5 C 0.7751(2) 0.5030(5) 0.8566(8) 0.0650(16) Uani 1 d . . . H5A H 0.7810 0.4145 0.8564 0.078 Uiso 1 calc R . . H5B H 0.7521 0.5224 0.9513 0.078 Uiso 1 calc R . . C6 C 0.6639(2) 0.5627(5) 0.3303(7) 0.0591(14) Uani 1 d . . . C7 C 0.6143(3) 0.4849(6) 0.3707(11) 0.088(2) Uani 1 d . . . H7A H 0.5819 0.5356 0.3707 0.132 Uiso 1 calc R . . H7B H 0.6190 0.4483 0.4781 0.132 Uiso 1 calc R . . H7C H 0.6105 0.4211 0.2890 0.132 Uiso 1 calc R . . C8 C 0.6611(3) 0.6244(6) 0.1627(8) 0.0788(19) Uani 1 d . . . H8A H 0.6962 0.6607 0.1373 0.118 Uiso 1 calc R . . H8B H 0.6334 0.6875 0.1645 0.118 Uiso 1 calc R . . H8C H 0.6520 0.5644 0.0797 0.118 Uiso 1 calc R . . C9 C 0.9195(2) 0.6315(5) 0.7294(6) 0.0484(12) Uani 1 d . . . C10 C 0.9142(3) 0.6342(7) 0.5585(7) 0.0670(17) Uani 1 d . . . H10 H 0.8802 0.6189 0.5098 0.080 Uiso 1 calc R . . C11 C 0.9596(3) 0.6598(8) 0.4597(10) 0.088(2) Uani 1 d . . . H11 H 0.9559 0.6612 0.3450 0.106 Uiso 1 calc R . . C12 C 1.0095(3) 0.6828(8) 0.5298(9) 0.081(2) Uani 1 d . . . H12 H 1.0395 0.7021 0.4630 0.097 Uiso 1 calc R . . C13 C 1.0158(3) 0.6776(7) 0.6994(10) 0.081(2) Uani 1 d . . . H13 H 1.0502 0.6900 0.7471 0.098 Uiso 1 calc R . . C14 C 0.9701(3) 0.6535(7) 0.7988(8) 0.0730(19) Uani 1 d . . . H14 H 0.9739 0.6524 0.9134 0.088 Uiso 1 calc R . . Cl1 Cl 0.4617(7) 0.4555(14) 0.7290(16) 0.265(8) Uani 0.50 d P A -1 Cl2 Cl 0.5004(5) 0.4426(9) 1.0514(8) 0.192(5) Uani 0.50 d P A -1 Cl3 Cl 0.5514(6) 0.5993(10) 0.8217(15) 0.210(7) Uani 0.50 d P A -1 C15 C 0.4862(8) 0.5317(19) 0.861(3) 0.149(10) Uani 0.50 d P A -1 H15 H 0.4602 0.5977 0.8884 0.179 Uiso 0.50 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0787(2) 0.0490(2) 0.0667(2) -0.01138(19) 0.0048(2) 0.00916(17) I2 0.0942(3) 0.0566(2) 0.0602(2) 0.0075(2) -0.0127(2) 0.01584(19) Sn1 0.05254(17) 0.03753(17) 0.05137(18) -0.00049(17) -0.00387(17) 0.00021(14) O4 0.060(2) 0.0325(18) 0.073(3) 0.0018(16) -0.0134(18) 0.0079(17) O1 0.064(2) 0.0382(19) 0.084(3) -0.0140(18) -0.026(2) 0.0105(17) O2 0.050(2) 0.048(2) 0.083(3) -0.0138(19) -0.0142(18) 0.0068(17) O3 0.059(2) 0.0317(18) 0.082(2) 0.0048(18) -0.0220(19) -0.0072(17) C1 0.049(3) 0.038(3) 0.058(3) -0.004(2) -0.003(2) 0.003(2) C2 0.052(3) 0.032(3) 0.063(3) 0.002(2) -0.009(2) -0.001(2) C3 0.048(3) 0.035(3) 0.064(4) -0.006(2) -0.007(2) -0.003(2) C4 0.052(3) 0.039(3) 0.068(4) 0.009(3) -0.009(3) -0.011(2) C5 0.070(3) 0.050(3) 0.076(4) 0.018(3) -0.019(3) -0.016(3) C6 0.055(3) 0.041(3) 0.082(4) -0.012(3) -0.017(3) 0.005(2) C7 0.072(4) 0.072(4) 0.120(6) -0.015(5) -0.014(5) -0.012(3) C8 0.097(5) 0.060(4) 0.080(4) -0.002(3) -0.026(4) 0.010(4) C9 0.049(3) 0.041(3) 0.056(3) 0.004(2) -0.004(2) 0.006(2) C10 0.059(3) 0.093(5) 0.050(3) -0.007(3) -0.003(3) 0.005(3) C11 0.084(5) 0.119(7) 0.061(4) -0.004(4) 0.001(4) 0.002(5) C12 0.072(5) 0.090(5) 0.081(5) 0.014(4) 0.022(4) 0.008(4) C13 0.053(4) 0.092(5) 0.099(5) 0.015(5) -0.002(4) -0.007(4) C14 0.069(4) 0.090(5) 0.060(4) 0.009(3) -0.013(3) -0.015(4) Cl1 0.313(18) 0.253(17) 0.230(12) -0.093(12) -0.127(12) -0.027(12) Cl2 0.147(4) 0.278(14) 0.152(5) 0.081(6) 0.020(6) 0.025(11) Cl3 0.244(9) 0.153(8) 0.233(12) 0.111(8) -0.095(10) -0.077(7) C15 0.116(17) 0.122(18) 0.21(2) -0.076(18) -0.062(16) 0.051(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Sn1 2.7121(5) . ? I2 Sn1 2.7684(5) . ? Sn1 C9 2.115(5) . ? Sn1 C5 2.127(5) . ? Sn1 O3 2.588(4) . ? O4 C1 1.401(6) . ? O4 C4 1.432(7) . ? O1 C1 1.425(6) . ? O1 C6 1.441(6) . ? O2 C6 1.411(6) . ? O2 C2 1.427(6) . ? O3 C3 1.443(6) . ? O3 H3 0.8200 . ? C1 C2 1.543(7) . ? C1 H1 0.9800 . ? C2 C3 1.516(8) . ? C2 H2 0.9800 . ? C3 C4 1.529(7) . ? C3 H3A 0.9800 . ? C4 C5 1.495(8) . ? C4 H4 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.504(8) . ? C6 C8 1.511(8) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C14 1.369(8) . ? C9 C10 1.385(8) . ? C10 C11 1.387(10) . ? C10 H10 0.9300 . ? C11 C12 1.361(11) . ? C11 H11 0.9300 . ? C12 C13 1.378(10) . ? C12 H12 0.9300 . ? C13 C14 1.394(9) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? Cl1 C15 1.47(2) . ? Cl2 C15 1.85(3) . ? Cl3 C15 1.77(3) . ? C15 H15 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 Sn1 C5 134.4(2) . . ? C9 Sn1 O3 86.47(16) . . ? C5 Sn1 O3 72.31(17) . . ? C9 Sn1 I1 107.32(14) . . ? C5 Sn1 I1 110.53(19) . . ? O3 Sn1 I1 85.45(8) . . ? C9 Sn1 I2 104.02(14) . . ? C5 Sn1 I2 96.22(15) . . ? O3 Sn1 I2 168.20(8) . . ? I1 Sn1 I2 96.329(17) . . ? C1 O4 C4 109.0(4) . . ? C1 O1 C6 109.2(4) . . ? C6 O2 C2 108.1(4) . . ? C3 O3 Sn1 112.0(3) . . ? C3 O3 H3 109.5 . . ? Sn1 O3 H3 129.9 . . ? O4 C1 O1 111.0(4) . . ? O4 C1 C2 106.7(4) . . ? O1 C1 C2 104.7(4) . . ? O4 C1 H1 111.4 . . ? O1 C1 H1 111.4 . . ? C2 C1 H1 111.4 . . ? O2 C2 C3 107.3(5) . . ? O2 C2 C1 103.9(4) . . ? C3 C2 C1 104.2(4) . . ? O2 C2 H2 113.5 . . ? C3 C2 H2 113.5 . . ? C1 C2 H2 113.5 . . ? O3 C3 C2 109.6(4) . . ? O3 C3 C4 106.4(4) . . ? C2 C3 C4 101.4(4) . . ? O3 C3 H3A 112.9 . . ? C2 C3 H3A 112.9 . . ? C4 C3 H3A 112.9 . . ? O4 C4 C5 109.6(5) . . ? O4 C4 C3 103.6(4) . . ? C5 C4 C3 116.9(5) . . ? O4 C4 H4 108.8 . . ? C5 C4 H4 108.8 . . ? C3 C4 H4 108.8 . . ? C4 C5 Sn1 115.1(4) . . ? C4 C5 H5A 108.5 . . ? Sn1 C5 H5A 108.5 . . ? C4 C5 H5B 108.5 . . ? Sn1 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? O2 C6 O1 105.4(4) . . ? O2 C6 C7 108.2(5) . . ? O1 C6 C7 108.5(5) . . ? O2 C6 C8 111.2(5) . . ? O1 C6 C8 109.1(5) . . ? C7 C6 C8 114.0(5) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 119.1(6) . . ? C14 C9 Sn1 118.5(4) . . ? C10 C9 Sn1 122.4(4) . . ? C9 C10 C11 120.1(6) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 120.3(7) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 120.2(7) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 119.4(7) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C9 C14 C13 120.7(6) . . ? C9 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? Cl1 C15 Cl3 118(2) . . ? Cl1 C15 Cl2 112.5(15) . . ? Cl3 C15 Cl2 101.4(10) . . ? Cl1 C15 H15 108.2 . . ? Cl3 C15 H15 108.2 . . ? Cl2 C15 H15 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 Sn1 O3 C3 139.3(3) . . . . ? C5 Sn1 O3 C3 0.3(3) . . . . ? I1 Sn1 O3 C3 -113.0(3) . . . . ? I2 Sn1 O3 C3 -13.8(7) . . . . ? C4 O4 C1 O1 -95.5(4) . . . . ? C4 O4 C1 C2 18.0(5) . . . . ? C6 O1 C1 O4 120.2(5) . . . . ? C6 O1 C1 C2 5.4(6) . . . . ? C6 O2 C2 C3 -136.8(5) . . . . ? C6 O2 C2 C1 -26.8(5) . . . . ? O4 C1 C2 O2 -105.0(5) . . . . ? O1 C1 C2 O2 12.7(5) . . . . ? O4 C1 C2 C3 7.3(5) . . . . ? O1 C1 C2 C3 125.0(4) . . . . ? Sn1 O3 C3 C2 -130.4(4) . . . . ? Sn1 O3 C3 C4 -21.6(5) . . . . ? O2 C2 C3 O3 -165.4(4) . . . . ? C1 C2 C3 O3 84.8(5) . . . . ? O2 C2 C3 C4 82.5(5) . . . . ? C1 C2 C3 C4 -27.3(5) . . . . ? C1 O4 C4 C5 -161.3(4) . . . . ? C1 O4 C4 C3 -35.9(5) . . . . ? O3 C3 C4 O4 -76.2(5) . . . . ? C2 C3 C4 O4 38.4(5) . . . . ? O3 C3 C4 C5 44.4(7) . . . . ? C2 C3 C4 C5 159.0(5) . . . . ? O4 C4 C5 Sn1 69.4(5) . . . . ? C3 C4 C5 Sn1 -47.9(7) . . . . ? C9 Sn1 C5 C4 -43.2(6) . . . . ? O3 Sn1 C5 C4 23.0(4) . . . . ? I1 Sn1 C5 C4 101.0(4) . . . . ? I2 Sn1 C5 C4 -159.8(4) . . . . ? C2 O2 C6 O1 30.7(6) . . . . ? C2 O2 C6 C7 146.6(5) . . . . ? C2 O2 C6 C8 -87.4(5) . . . . ? C1 O1 C6 O2 -21.9(6) . . . . ? C1 O1 C6 C7 -137.7(5) . . . . ? C1 O1 C6 C8 97.6(5) . . . . ? C5 Sn1 C9 C14 -158.8(5) . . . . ? O3 Sn1 C9 C14 140.3(5) . . . . ? I1 Sn1 C9 C14 56.2(5) . . . . ? I2 Sn1 C9 C14 -45.2(5) . . . . ? C5 Sn1 C9 C10 20.2(6) . . . . ? O3 Sn1 C9 C10 -40.7(5) . . . . ? I1 Sn1 C9 C10 -124.8(5) . . . . ? I2 Sn1 C9 C10 133.9(5) . . . . ? C14 C9 C10 C11 -0.4(11) . . . . ? Sn1 C9 C10 C11 -179.5(5) . . . . ? C9 C10 C11 C12 -0.2(12) . . . . ? C10 C11 C12 C13 1.8(14) . . . . ? C11 C12 C13 C14 -2.6(15) . . . . ? C10 C9 C14 C13 -0.4(10) . . . . ? Sn1 C9 C14 C13 178.6(6) . . . . ? C12 C13 C14 C9 1.9(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O1 0.82 2.00 2.819(5) 179.7 4_656 C4 H4 I1 0.98 3.09 3.833(5) 133.9 4_647 C15 H15 I1 0.98 3.12 4.020(17) 153.5 3_467 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.311 _refine_diff_density_min -0.692 _refine_diff_density_rms 0.104 #===END data_(D)-6 _database_code_CSD 185953 # Note that this reports further refinement of a previously reported (by us) # structure with the original intensity data _publ_requested_journal test _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-C-(Triphenylstannyl)methyl-1,2:5,6-di-O-isopropylidene-alpha-D- allofuranose ; _chemical_name_common ? _chemical_formula_moiety 'C31 H36 O6 Sn' _chemical_formula_sum 'C31 H36 O6 Sn' _chemical_formula_weight 623.29 _chemical_melting_point 394-396 _chemical_absolute_configuration rmad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.070(4) _cell_length_b 13.074(12) _cell_length_c 37.69(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2991(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 14 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 5.05 _exptl_crystal_preparation 'from hexane as solvent' _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.894 _exptl_absorpt_correction_type none # SHELXL-97 Tmin/max calc. (from xstl. dims.) 0.6635/0.9319 - no corrn. applied # _exptl_absorpt_correction_T_min 0.6635 # _exptl_absorpt_correction_T_max 0.9319 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nicolet P3' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3077 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.5258 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3063 _reflns_number_gt 1862 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Nicolet P3 software (Nicolet, 1980)' _computing_cell_refinement 'Nicolet P3 software (Nicolet, 1980)' _computing_data_reduction 'RDNIC (Howie, 1980)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-H refined anisotropically. H in calculated positions and refined with a riding model. Only symmetry unique (for orthorhombic) data available but R(gt) and Flack x parameters of 0.0560 and -0.05(7) resp. vvs. 0.0577 and 0.82(8) for inverted structure confirm that the absolute structure is correct. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0325P)^2^+4.6114P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(7) _refine_ls_number_reflns 3063 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1312 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn -0.0064(2) 0.96504(5) 0.097642(17) 0.0394(2) Uani 1 d . . . C1 C 0.381(2) 0.8404(11) 0.2097(3) 0.061(4) Uani 1 d . . . H1 H 0.4900 0.8946 0.2136 0.073 Uiso 1 calc R . . O1 O 0.3109(16) 0.7986(8) 0.2417(2) 0.072(3) Uani 1 d . . . C2 C 0.178(2) 0.8816(10) 0.1918(3) 0.054(4) Uani 1 d . . . H2 H 0.1910 0.9549 0.1866 0.065 Uiso 1 calc R . . O2 O 0.000(3) 0.8603(6) 0.21477(16) 0.061(2) Uani 1 d . . . C3 C 0.151(2) 0.8190(11) 0.1585(3) 0.041(4) Uani 1 d . . . O3 O -0.0754(14) 0.7965(10) 0.1496(2) 0.049(3) Uani 1 d . . . H3 H -0.1475 0.7905 0.1679 0.074 Uiso 1 calc R . . C4 C 0.283(2) 0.7228(10) 0.1675(3) 0.056(4) Uani 1 d . . . H4 H 0.1933 0.6801 0.1832 0.067 Uiso 1 calc R . . O4 O 0.467(2) 0.7621(7) 0.1876(2) 0.064(3) Uani 1 d . . . C5 C 0.374(3) 0.6559(10) 0.1384(4) 0.072(5) Uani 1 d . . . H5 H 0.4556 0.6986 0.1215 0.086 Uiso 1 calc R . . O5 O 0.199(2) 0.6068(8) 0.1205(3) 0.100(4) Uani 1 d . . . C6 C 0.097(3) 0.8382(13) 0.2493(4) 0.071(5) Uani 1 d . . . C7 C -0.041(4) 0.7554(14) 0.2650(3) 0.121(8) Uani 1 d . . . H7A H -0.0254 0.6943 0.2511 0.181 Uiso 1 calc R . . H7B H -0.1922 0.7763 0.2651 0.181 Uiso 1 calc R . . H7C H 0.0069 0.7422 0.2888 0.181 Uiso 1 calc R . . C8 C 0.111(3) 0.9352(14) 0.2705(4) 0.137(9) Uani 1 d . . . H8A H 0.1680 0.9202 0.2937 0.205 Uiso 1 calc R . . H8B H -0.0334 0.9646 0.2727 0.205 Uiso 1 calc R . . H8C H 0.2068 0.9827 0.2588 0.205 Uiso 1 calc R . . C9 C 0.242(2) 0.8771(9) 0.1252(3) 0.047(3) Uani 1 d . . . H9A H 0.3046 0.8277 0.1089 0.057 Uiso 1 calc R . . H9B H 0.3588 0.9227 0.1327 0.057 Uiso 1 calc R . . C10 C 0.525(5) 0.5712(11) 0.1516(4) 0.109(6) Uani 1 d . . . H10A H 0.6783 0.5916 0.1515 0.131 Uiso 1 calc R . . H10B H 0.4839 0.5481 0.1752 0.131 Uiso 1 calc R . . O6 O 0.478(3) 0.4942(8) 0.1247(4) 0.126(5) Uani 1 d . . . C11 C 0.256(4) 0.5041(11) 0.1150(5) 0.080(5) Uani 1 d . . . C12 C 0.112(3) 0.4360(14) 0.1342(5) 0.172(11) Uani 1 d . . . H12A H 0.1656 0.3672 0.1323 0.258 Uiso 1 calc R . . H12B H -0.0339 0.4398 0.1244 0.258 Uiso 1 calc R . . H12C H 0.1075 0.4558 0.1587 0.258 Uiso 1 calc R . . C13 C 0.259(3) 0.4864(13) 0.0757(5) 0.144(9) Uani 1 d . . . H13A H 0.3372 0.5410 0.0642 0.217 Uiso 1 calc R . . H13B H 0.1102 0.4843 0.0669 0.217 Uiso 1 calc R . . H13C H 0.3304 0.4225 0.0706 0.217 Uiso 1 calc R . . C14 C -0.213(2) 0.8618(9) 0.0686(3) 0.040(3) Uani 1 d . . . C15 C -0.380(2) 0.9001(10) 0.0483(3) 0.056(4) Uani 1 d . . . H15 H -0.4027 0.9704 0.0473 0.067 Uiso 1 calc R . . C16 C -0.516(4) 0.8350(10) 0.0292(3) 0.068(4) Uani 1 d . . . H16 H -0.6288 0.8617 0.0154 0.081 Uiso 1 calc R . . C17 C -0.483(4) 0.7290(10) 0.0308(3) 0.064(4) Uani 1 d . . . H17 H -0.5733 0.6843 0.0183 0.077 Uiso 1 calc R . . C18 C -0.314(2) 0.6936(10) 0.0513(3) 0.057(4) Uani 1 d . . . H18 H -0.2897 0.6235 0.0526 0.068 Uiso 1 calc R . . C19 C -0.180(2) 0.7570(9) 0.0699(3) 0.052(3) Uani 1 d . . . H19 H -0.0667 0.7302 0.0836 0.062 Uiso 1 calc R . . C20 C -0.187(2) 1.0700(9) 0.1310(3) 0.047(4) Uani 1 d . . . C21 C -0.287(2) 1.0459(10) 0.1628(3) 0.063(4) Uani 1 d . . . H21 H -0.2730 0.9793 0.1712 0.076 Uiso 1 calc R . . C22 C -0.405(3) 1.1129(12) 0.1827(4) 0.089(6) Uani 1 d . . . H22 H -0.4683 1.0925 0.2040 0.106 Uiso 1 calc R . . C23 C -0.430(3) 1.2093(14) 0.1708(4) 0.091(7) Uani 1 d . . . H23 H -0.5096 1.2557 0.1844 0.109 Uiso 1 calc R . . C24 C -0.341(3) 1.2407(10) 0.1399(4) 0.080(5) Uani 1 d . . . H24 H -0.3658 1.3068 0.1317 0.096 Uiso 1 calc R . . C25 C -0.212(2) 1.1727(9) 0.1203(3) 0.053(4) Uani 1 d . . . H25 H -0.1413 1.1954 0.0998 0.064 Uiso 1 calc R . . C26 C 0.150(2) 1.0602(9) 0.0590(3) 0.048(3) Uani 1 d . . . C27 C 0.117(2) 1.0447(10) 0.0225(3) 0.054(3) Uani 1 d . . . H27 H 0.0116 0.9974 0.0152 0.064 Uiso 1 calc R . . C28 C 0.235(3) 1.0980(10) -0.0030(3) 0.061(4) Uani 1 d . . . H28 H 0.2126 1.0837 -0.0269 0.073 Uiso 1 calc R . . C29 C 0.387(3) 1.1717(10) 0.0067(4) 0.068(4) Uani 1 d . . . H29 H 0.4677 1.2077 -0.0101 0.081 Uiso 1 calc R . . C30 C 0.411(2) 1.1893(10) 0.0426(4) 0.060(4) Uani 1 d . . . H30 H 0.5098 1.2397 0.0499 0.072 Uiso 1 calc R . . C31 C 0.297(2) 1.1359(10) 0.0683(4) 0.058(4) Uani 1 d . . . H31 H 0.3196 1.1511 0.0921 0.069 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.0401(4) 0.0381(3) 0.0400(3) -0.0036(4) -0.0019(8) 0.0006(9) C1 0.073(10) 0.079(10) 0.030(7) -0.003(7) -0.007(7) -0.005(9) O1 0.063(6) 0.122(9) 0.030(5) 0.005(6) 0.001(5) 0.010(7) C2 0.065(9) 0.062(9) 0.036(7) -0.002(7) -0.003(7) -0.009(8) O2 0.064(5) 0.088(6) 0.031(4) -0.002(4) 0.008(9) 0.003(12) C3 0.061(10) 0.044(8) 0.018(6) -0.003(6) -0.003(7) -0.011(8) O3 0.052(7) 0.064(7) 0.033(5) -0.009(5) 0.013(4) -0.011(5) C4 0.070(10) 0.052(8) 0.046(8) -0.010(7) -0.004(8) 0.011(8) O4 0.054(8) 0.077(6) 0.061(5) 0.008(5) -0.001(6) 0.006(7) C5 0.090(12) 0.047(9) 0.079(11) -0.002(8) 0.004(10) 0.016(10) O5 0.129(11) 0.072(7) 0.098(8) -0.051(7) -0.032(8) 0.039(8) C6 0.072(11) 0.110(13) 0.032(7) 0.026(8) 0.004(8) 0.019(10) C7 0.12(2) 0.196(19) 0.051(8) 0.051(11) 0.026(13) -0.015(19) C8 0.17(2) 0.19(2) 0.061(9) -0.065(12) -0.015(11) 0.063(16) C9 0.041(8) 0.056(8) 0.045(7) -0.001(7) -0.001(7) -0.004(8) C10 0.126(18) 0.093(11) 0.109(12) -0.039(10) -0.001(19) 0.027(19) O6 0.093(9) 0.079(8) 0.207(12) -0.005(8) -0.061(12) 0.045(11) C11 0.101(14) 0.046(9) 0.092(12) 0.000(8) 0.031(12) 0.019(9) C12 0.17(2) 0.125(18) 0.23(2) 0.021(17) 0.13(2) -0.007(16) C13 0.124(18) 0.077(14) 0.23(2) -0.030(15) 0.065(19) -0.023(14) C14 0.040(8) 0.042(8) 0.038(7) -0.002(6) -0.001(6) -0.001(7) C15 0.053(9) 0.052(8) 0.063(9) -0.014(7) -0.008(8) 0.004(8) C16 0.054(9) 0.077(9) 0.072(8) -0.008(7) -0.018(14) 0.011(15) C17 0.058(10) 0.080(9) 0.053(7) -0.027(7) -0.005(12) -0.048(13) C18 0.072(11) 0.039(8) 0.059(9) -0.009(7) -0.007(9) -0.002(8) C19 0.055(9) 0.052(8) 0.047(7) -0.004(7) -0.004(7) 0.010(8) C20 0.037(7) 0.036(7) 0.068(9) -0.022(6) -0.005(7) -0.006(6) C21 0.084(10) 0.035(7) 0.070(8) -0.013(8) 0.028(8) -0.008(9) C22 0.101(15) 0.071(10) 0.094(12) -0.028(10) 0.045(10) 0.003(11) C23 0.100(19) 0.097(14) 0.076(11) -0.046(11) 0.014(11) 0.010(13) C24 0.101(14) 0.033(8) 0.105(13) -0.028(9) -0.027(12) 0.017(10) C25 0.055(9) 0.049(8) 0.056(8) -0.003(7) 0.010(8) -0.005(8) C26 0.045(8) 0.039(8) 0.059(8) 0.001(6) -0.002(7) 0.012(7) C27 0.057(8) 0.041(7) 0.062(7) -0.002(8) -0.009(7) -0.005(8) C28 0.074(11) 0.060(9) 0.049(8) 0.011(7) 0.000(8) 0.016(9) C29 0.079(11) 0.063(9) 0.061(9) 0.031(8) 0.016(8) 0.003(9) C30 0.058(10) 0.054(9) 0.068(9) 0.003(8) 0.008(8) -0.006(8) C31 0.056(9) 0.057(9) 0.060(9) 0.004(8) 0.008(8) -0.003(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sn1 C26 2.137(12) . ? Sn1 C14 2.144(11) . ? Sn1 C20 2.161(12) . ? Sn1 C9 2.161(12) . ? Sn1 O3 2.977(10) . ? C1 O1 1.389(13) . ? C1 O4 1.420(14) . ? C1 C2 1.504(17) . ? C1 H1 0.9800 . ? O1 C6 1.426(17) . ? C2 O2 1.413(16) . ? C2 C3 1.508(15) . ? C2 H2 0.9800 . ? O2 C6 1.456(15) . ? C3 O3 1.444(14) . ? C3 C4 1.528(19) . ? C3 C9 1.565(16) . ? O3 H3 0.8201 . ? C4 O4 1.444(15) . ? C4 C5 1.508(16) . ? C4 H4 0.9800 . ? C5 O5 1.416(17) . ? C5 C10 1.52(2) . ? C5 H5 0.9800 . ? O5 C11 1.403(16) . ? C6 C7 1.49(2) . ? C6 C8 1.503(19) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O6 1.458(15) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? O6 C11 1.40(2) . ? C11 C12 1.44(2) . ? C11 C13 1.50(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.362(15) . ? C14 C19 1.385(15) . ? C15 C16 1.387(19) . ? C15 H15 0.9300 . ? C16 C17 1.401(17) . ? C16 H16 0.9300 . ? C17 C18 1.37(2) . ? C17 H17 0.9300 . ? C18 C19 1.354(16) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.380(15) . ? C20 C25 1.410(15) . ? C21 C22 1.357(16) . ? C21 H21 0.9300 . ? C22 C23 1.346(19) . ? C22 H22 0.9300 . ? C23 C24 1.347(19) . ? C23 H23 0.9300 . ? C24 C25 1.397(17) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C31 1.377(16) . ? C26 C27 1.405(14) . ? C27 C28 1.388(16) . ? C27 H27 0.9300 . ? C28 C29 1.380(18) . ? C28 H28 0.9300 . ? C29 C30 1.382(16) . ? C29 H29 0.9300 . ? C30 C31 1.380(16) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C26 Sn1 C14 106.2(5) . . ? C26 Sn1 C20 104.7(4) . . ? C14 Sn1 C20 113.5(5) . . ? C26 Sn1 C9 109.1(5) . . ? C14 Sn1 C9 108.6(4) . . ? C20 Sn1 C9 114.3(4) . . ? C26 Sn1 O3 160.2(4) . . ? C14 Sn1 O3 77.8(4) . . ? C20 Sn1 O3 90.9(4) . . ? C9 Sn1 O3 52.2(4) . . ? O1 C1 O4 109.8(11) . . ? O1 C1 C2 106.3(11) . . ? O4 C1 C2 107.1(10) . . ? O1 C1 H1 111.2 . . ? O4 C1 H1 111.2 . . ? C2 C1 H1 111.2 . . ? C1 O1 C6 108.0(11) . . ? O2 C2 C1 106.2(9) . . ? O2 C2 C3 108.6(10) . . ? C1 C2 C3 105.7(11) . . ? O2 C2 H2 112.0 . . ? C1 C2 H2 112.0 . . ? C3 C2 H2 112.0 . . ? C2 O2 C6 106.1(13) . . ? O3 C3 C2 114.0(12) . . ? O3 C3 C4 112.5(13) . . ? C2 C3 C4 101.8(10) . . ? O3 C3 C9 104.4(11) . . ? C2 C3 C9 111.4(11) . . ? C4 C3 C9 113.1(11) . . ? C3 O3 Sn1 82.4(8) . . ? C3 O3 H3 109.5 . . ? Sn1 O3 H3 134.3 . . ? O4 C4 C5 107.6(12) . . ? O4 C4 C3 103.3(10) . . ? C5 C4 C3 120.6(11) . . ? O4 C4 H4 108.3 . . ? C5 C4 H4 108.3 . . ? C3 C4 H4 108.3 . . ? C1 O4 C4 106.3(11) . . ? O5 C5 C4 109.4(13) . . ? O5 C5 C10 106.2(12) . . ? C4 C5 C10 113.9(13) . . ? O5 C5 H5 109.1 . . ? C4 C5 H5 109.1 . . ? C10 C5 H5 109.1 . . ? C11 O5 C5 108.5(13) . . ? O1 C6 O2 105.2(12) . . ? O1 C6 C7 109.1(14) . . ? O2 C6 C7 105.8(14) . . ? O1 C6 C8 111.3(15) . . ? O2 C6 C8 109.4(12) . . ? C7 C6 C8 115.6(14) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 Sn1 113.5(9) . . ? C3 C9 H9A 108.9 . . ? Sn1 C9 H9A 108.9 . . ? C3 C9 H9B 108.9 . . ? Sn1 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? O6 C10 C5 99.0(14) . . ? O6 C10 H10A 112.0 . . ? C5 C10 H10A 112.0 . . ? O6 C10 H10B 112.0 . . ? C5 C10 H10B 112.0 . . ? H10A C10 H10B 109.6 . . ? C11 O6 C10 107.9(17) . . ? O6 C11 O5 106.8(15) . . ? O6 C11 C12 113.3(16) . . ? O5 C11 C12 111.4(15) . . ? O6 C11 C13 103.5(16) . . ? O5 C11 C13 107.2(14) . . ? C12 C11 C13 114.0(18) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 119.4(12) . . ? C15 C14 Sn1 119.3(9) . . ? C19 C14 Sn1 121.3(10) . . ? C14 C15 C16 120.4(13) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 120.1(19) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 117.7(16) . . ? C18 C17 H17 121.2 . . ? C16 C17 H17 121.2 . . ? C19 C18 C17 122.4(13) . . ? C19 C18 H18 118.8 . . ? C17 C18 H18 118.8 . . ? C18 C19 C14 120.0(13) . . ? C18 C19 H19 120.0 . . ? C14 C19 H19 120.0 . . ? C21 C20 C25 114.9(12) . . ? C21 C20 Sn1 125.7(9) . . ? C25 C20 Sn1 119.4(10) . . ? C22 C21 C20 124.3(13) . . ? C22 C21 H21 117.8 . . ? C20 C21 H21 117.8 . . ? C23 C22 C21 118.6(15) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C22 C23 C24 121.9(16) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C23 C24 C25 119.2(14) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C24 C25 C20 120.9(13) . . ? C24 C25 H25 119.6 . . ? C20 C25 H25 119.6 . . ? C31 C26 C27 116.4(12) . . ? C31 C26 Sn1 122.3(10) . . ? C27 C26 Sn1 121.2(10) . . ? C28 C27 C26 122.0(12) . . ? C28 C27 H27 119.0 . . ? C26 C27 H27 119.0 . . ? C29 C28 C27 120.9(12) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 C30 116.5(13) . . ? C28 C29 H29 121.8 . . ? C30 C29 H29 121.8 . . ? C31 C30 C29 123.2(14) . . ? C31 C30 H30 118.4 . . ? C29 C30 H30 118.4 . . ? C26 C31 C30 120.8(13) . . ? C26 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C1 O1 C6 -132.8(13) . . . . ? C2 C1 O1 C6 -17.3(15) . . . . ? O1 C1 C2 O2 -0.3(14) . . . . ? O4 C1 C2 O2 117.0(10) . . . . ? O1 C1 C2 C3 -115.6(11) . . . . ? O4 C1 C2 C3 1.7(14) . . . . ? C1 C2 O2 C6 17.3(13) . . . . ? C3 C2 O2 C6 130.5(12) . . . . ? O2 C2 C3 O3 29.1(17) . . . . ? C1 C2 C3 O3 142.7(13) . . . . ? O2 C2 C3 C4 -92.3(12) . . . . ? C1 C2 C3 C4 21.3(13) . . . . ? O2 C2 C3 C9 146.9(11) . . . . ? C1 C2 C3 C9 -99.5(13) . . . . ? C2 C3 O3 Sn1 101.7(11) . . . . ? C4 C3 O3 Sn1 -143.0(10) . . . . ? C9 C3 O3 Sn1 -20.0(9) . . . . ? C26 Sn1 O3 C3 39.2(15) . . . . ? C14 Sn1 O3 C3 143.2(8) . . . . ? C20 Sn1 O3 C3 -102.9(8) . . . . ? C9 Sn1 O3 C3 17.7(7) . . . . ? O3 C3 C4 O4 -159.4(10) . . . . ? C2 C3 C4 O4 -36.9(12) . . . . ? C9 C3 C4 O4 82.7(12) . . . . ? O3 C3 C4 C5 80.6(17) . . . . ? C2 C3 C4 C5 -156.9(13) . . . . ? C9 C3 C4 C5 -37.4(18) . . . . ? O1 C1 O4 C4 89.0(12) . . . . ? C2 C1 O4 C4 -26.0(13) . . . . ? C5 C4 O4 C1 168.2(10) . . . . ? C3 C4 O4 C1 39.7(12) . . . . ? O4 C4 C5 O5 173.6(11) . . . . ? C3 C4 C5 O5 -68.6(17) . . . . ? O4 C4 C5 C10 54.9(18) . . . . ? C3 C4 C5 C10 172.8(15) . . . . ? C4 C5 O5 C11 -136.5(12) . . . . ? C10 C5 O5 C11 -13.2(18) . . . . ? C1 O1 C6 O2 28.2(16) . . . . ? C1 O1 C6 C7 141.2(12) . . . . ? C1 O1 C6 C8 -90.1(13) . . . . ? C2 O2 C6 O1 -27.9(15) . . . . ? C2 O2 C6 C7 -143.2(12) . . . . ? C2 O2 C6 C8 91.7(14) . . . . ? O3 C3 C9 Sn1 30.6(13) . . . . ? C2 C3 C9 Sn1 -92.9(11) . . . . ? C4 C3 C9 Sn1 153.2(8) . . . . ? C26 Sn1 C9 C3 170.0(8) . . . . ? C14 Sn1 C9 C3 -74.7(9) . . . . ? C20 Sn1 C9 C3 53.2(10) . . . . ? O3 Sn1 C9 C3 -17.6(7) . . . . ? O5 C5 C10 O6 28(2) . . . . ? C4 C5 C10 O6 148.6(15) . . . . ? C5 C10 O6 C11 -34(2) . . . . ? C10 O6 C11 O5 28.2(18) . . . . ? C10 O6 C11 C12 -94.8(17) . . . . ? C10 O6 C11 C13 141.2(14) . . . . ? C5 O5 C11 O6 -8.6(18) . . . . ? C5 O5 C11 C12 115.6(19) . . . . ? C5 O5 C11 C13 -119.0(17) . . . . ? C26 Sn1 C14 C15 -61.3(10) . . . . ? C20 Sn1 C14 C15 53.1(10) . . . . ? C9 Sn1 C14 C15 -178.5(9) . . . . ? O3 Sn1 C14 C15 138.7(10) . . . . ? C26 Sn1 C14 C19 118.5(10) . . . . ? C20 Sn1 C14 C19 -127.1(10) . . . . ? C9 Sn1 C14 C19 1.3(12) . . . . ? O3 Sn1 C14 C19 -41.5(10) . . . . ? C19 C14 C15 C16 0(2) . . . . ? Sn1 C14 C15 C16 179.9(11) . . . . ? C14 C15 C16 C17 0(3) . . . . ? C15 C16 C17 C18 0(3) . . . . ? C16 C17 C18 C19 0(2) . . . . ? C17 C18 C19 C14 0(2) . . . . ? C15 C14 C19 C18 -0.3(19) . . . . ? Sn1 C14 C19 C18 179.9(9) . . . . ? C26 Sn1 C20 C21 -169.5(11) . . . . ? C14 Sn1 C20 C21 75.1(12) . . . . ? C9 Sn1 C20 C21 -50.2(12) . . . . ? O3 Sn1 C20 C21 -1.9(11) . . . . ? C26 Sn1 C20 C25 11.3(11) . . . . ? C14 Sn1 C20 C25 -104.1(10) . . . . ? C9 Sn1 C20 C25 130.6(10) . . . . ? O3 Sn1 C20 C25 178.9(10) . . . . ? C25 C20 C21 C22 1(2) . . . . ? Sn1 C20 C21 C22 -178.0(12) . . . . ? C20 C21 C22 C23 1(3) . . . . ? C21 C22 C23 C24 0(3) . . . . ? C22 C23 C24 C25 -3(3) . . . . ? C23 C24 C25 C20 5(2) . . . . ? C21 C20 C25 C24 -4(2) . . . . ? Sn1 C20 C25 C24 175.4(10) . . . . ? C14 Sn1 C26 C31 -179.7(10) . . . . ? C20 Sn1 C26 C31 59.9(11) . . . . ? C9 Sn1 C26 C31 -62.8(11) . . . . ? O3 Sn1 C26 C31 -80.7(15) . . . . ? C14 Sn1 C26 C27 -3.0(11) . . . . ? C20 Sn1 C26 C27 -123.4(10) . . . . ? C9 Sn1 C26 C27 113.8(10) . . . . ? O3 Sn1 C26 C27 95.9(14) . . . . ? C31 C26 C27 C28 4.2(18) . . . . ? Sn1 C26 C27 C28 -172.7(9) . . . . ? C26 C27 C28 C29 -3(2) . . . . ? C27 C28 C29 C30 0(2) . . . . ? C28 C29 C30 C31 1(2) . . . . ? C27 C26 C31 C30 -3.1(19) . . . . ? Sn1 C26 C31 C30 173.7(10) . . . . ? C29 C30 C31 C26 0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O2 0.82 2.18 2.634(11) 114.9 . O3 H3 O4 0.82 2.48 3.158(14) 140.2 1_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.481 _refine_diff_density_min -0.786 _refine_diff_density_rms 0.105 #===END