# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_h13kcm1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H26 O6 P2 Sn' _chemical_formula_sum 'C10 H26 O6 P2 Sn' _chemical_formula_weight 422.94 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' P P 0.1023 0.0942 '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 _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1681(4) _cell_length_b 7.6308(4) _cell_length_c 11.3713(8) _cell_angle_alpha 84.310(4) _cell_angle_beta 82.173(3) _cell_angle_gamma 73.820(4) _cell_volume 425.79(5) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6111 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 214 _exptl_absorpt_coefficient_mu 1.704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6753 _exptl_absorpt_correction_T_max 0.9196 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method '288 2.0 degree images with \f and \w scans' _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5358 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 27.56 _reflns_number_total 1858 _reflns_number_gt 1828 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; DENZO-SCALEPACK Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press. ; _computing_structure_solution ; SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) J. Appl. Cryst. 32, 115-119 ; _computing_structure_refinement ; Sheldrick GM (2008) Acta Crystallogr A64:112--122 and C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich ShelXle: a Qt graphical user interface for SHELXL J. Appl. Cryst., 44, (2011) 1281-1284. ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _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. ; _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^)+(0.1694P)^2^+0.5087P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1858 _refine_ls_number_parameters 94 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.1882 _refine_ls_wR_factor_gt 0.1868 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn Sn 0.5000 0.5000 0.5000 0.0154(3) Uani 1 2 d S . . P P 0.1426(3) 0.2219(2) 0.40739(14) 0.0176(4) Uani 1 1 d . . . H H 0.30(2) 0.089(14) 0.448(9) 0.04(3) Uiso 1 1 d . . . O1 O 0.3036(9) 0.3573(7) 0.3929(4) 0.0243(10) Uani 1 1 d . . . O2 O -0.1279(9) 0.2685(6) 0.4801(4) 0.0226(9) Uani 1 1 d . . . O3 O 0.1198(11) 0.1796(8) 0.2768(5) 0.0319(12) Uani 1 1 d . . . C1 C 0.3669(13) 0.3513(9) 0.6540(6) 0.0215(12) Uani 1 1 d . . . H1A H 0.1668 0.3798 0.6598 0.026 Uiso 1 1 calc R . . H1B H 0.4393 0.2194 0.6409 0.026 Uiso 1 1 calc R . . C2 C 0.4412(17) 0.3823(11) 0.7729(6) 0.0320(15) Uani 1 1 d . . . H2A H 0.3579 0.5113 0.7916 0.038 Uiso 1 1 calc R . . H2B H 0.6405 0.3582 0.7690 0.038 Uiso 1 1 calc R . . C3 C 0.342(2) 0.2561(13) 0.8707(7) 0.043(2) Uani 1 1 d . . . H3A H 0.1426 0.2823 0.8744 0.052 Uiso 1 1 calc R . . H3B H 0.4216 0.1278 0.8496 0.052 Uiso 1 1 calc R . . C4 C 0.415(3) 0.276(2) 0.9925(9) 0.075(4) Uani 1 1 d . . . H4A H 0.6122 0.2473 0.9903 0.113 Uiso 1 1 calc R . . H4B H 0.3458 0.1918 1.0510 0.113 Uiso 1 1 calc R . . H4C H 0.3330 0.4019 1.0151 0.113 Uiso 1 1 calc R . . C5 C -0.0485(18) 0.0642(13) 0.2588(8) 0.0377(19) Uani 1 1 d . . . H5A H 0.0065 -0.0522 0.3056 0.057 Uiso 1 1 calc R . . H5B H -0.0277 0.0413 0.1742 0.057 Uiso 1 1 calc R . . H5C H -0.2387 0.1253 0.2842 0.057 Uiso 1 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 Sn 0.0110(4) 0.0184(4) 0.0188(4) -0.0013(2) -0.0006(2) -0.0075(2) P 0.0119(7) 0.0183(9) 0.0240(8) -0.0037(6) -0.0010(6) -0.0061(5) O1 0.024(2) 0.030(3) 0.025(2) -0.005(2) -0.0013(19) -0.0168(19) O2 0.019(2) 0.021(2) 0.026(2) -0.0020(17) 0.0026(16) -0.0055(17) O3 0.034(3) 0.042(3) 0.029(3) -0.012(2) 0.002(2) -0.025(2) C1 0.023(3) 0.020(3) 0.023(3) 0.001(2) 0.002(2) -0.011(2) C2 0.046(4) 0.031(4) 0.025(3) 0.002(3) -0.004(3) -0.020(3) C3 0.069(6) 0.041(5) 0.026(4) 0.005(3) -0.001(4) -0.029(4) C4 0.130(12) 0.085(9) 0.030(5) 0.009(5) -0.012(6) -0.064(9) C5 0.041(4) 0.041(5) 0.042(4) -0.017(4) -0.001(3) -0.025(4) _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 Sn C1 2.131(6) 2_666 ? Sn C1 2.131(6) . ? Sn O1 2.217(5) . ? Sn O1 2.217(5) 2_666 ? Sn O2 2.222(4) 1_655 ? Sn O2 2.222(4) 2_566 ? P O1 1.481(5) . ? P O2 1.493(4) . ? P O3 1.576(5) . ? P H 1.20(10) . ? O2 Sn 2.222(4) 1_455 ? O3 C5 1.445(9) . ? C1 C2 1.512(9) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.528(11) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.516(13) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 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 C1 Sn C1 180.000(1) 2_666 . ? C1 Sn O1 91.8(2) 2_666 . ? C1 Sn O1 88.2(2) . . ? C1 Sn O1 88.2(2) 2_666 2_666 ? C1 Sn O1 91.8(2) . 2_666 ? O1 Sn O1 180.0(2) . 2_666 ? C1 Sn O2 92.6(2) 2_666 1_655 ? C1 Sn O2 87.4(2) . 1_655 ? O1 Sn O2 88.67(18) . 1_655 ? O1 Sn O2 91.33(18) 2_666 1_655 ? C1 Sn O2 87.4(2) 2_666 2_566 ? C1 Sn O2 92.6(2) . 2_566 ? O1 Sn O2 91.33(18) . 2_566 ? O1 Sn O2 88.67(18) 2_666 2_566 ? O2 Sn O2 180.000(1) 1_655 2_566 ? O1 P O2 118.3(3) . . ? O1 P O3 105.1(3) . . ? O2 P O3 111.7(3) . . ? O1 P H 102(5) . . ? O2 P H 112(5) . . ? O3 P H 106(5) . . ? P O1 Sn 140.5(3) . . ? P O2 Sn 139.4(3) . 1_455 ? C5 O3 P 119.3(5) . . ? C2 C1 Sn 118.2(5) . . ? C2 C1 H1A 107.8 . . ? Sn C1 H1A 107.8 . . ? C2 C1 H1B 107.8 . . ? Sn C1 H1B 107.8 . . ? H1A C1 H1B 107.1 . . ? C1 C2 C3 110.3(6) . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C2 113.5(8) . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O3 C5 H5A 109.5 . . ? O3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 2.272 _refine_diff_density_min -0.784 _refine_diff_density_rms 0.128 _database_code_depnum_ccdc_archive 'CCDC 952820' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound2 #TrackingRef '14338_web_deposit_cif_file_1_MeenalAsija_1349000871.cif_EtPHOMe.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H16 O6 P2 Sn' _chemical_formula_sum 'C6 H16 O6 P2 Sn' _chemical_formula_weight 364.82 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' P P 0.1023 0.0942 '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/a' _symmetry_space_group_name_hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.172(7) _cell_length_b 15.548(2) _cell_length_c 5.393(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.617(4) _cell_angle_gamma 90.00 _cell_volume 659.9(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3348 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 24.99 _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.836 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 2.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.682 _exptl_absorpt_correction_T_max 0.804 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3598 _diffrn_reflns_av_R_equivalents 0.0936 _diffrn_reflns_av_sigmaI/netI 0.0852 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1126 _reflns_number_gt 722 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0942P)^2^+0.0000P] 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_number_reflns 1126 _refine_ls_number_parameters 72 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1009 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.1899 _refine_ls_wR_factor_gt 0.1744 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.130 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn Sn 0.5000 0.5000 1.0000 0.0355(5) Uani 1 2 d S . . P P 0.4258(4) 0.35474(18) 0.4695(4) 0.0343(7) Uani 1 1 d . . . O1 O 0.3925(11) 0.4109(6) 0.6727(15) 0.060(2) Uani 1 1 d . . . O2 O 0.4882(13) 0.3934(6) 0.2620(15) 0.067(3) Uani 1 1 d . . . O3 O 0.5522(12) 0.2806(6) 0.5832(16) 0.053(2) Uani 1 1 d . . . C1 C 0.2438(17) 0.5302(9) 0.993(3) 0.053(3) Uani 1 1 d . . . H1A H 0.1858 0.4767 1.0063 0.064 Uiso 1 1 calc R . . H1B H 0.2463 0.5637 1.1459 0.064 Uiso 1 1 calc R . . C2 C 0.140(2) 0.5778(14) 0.768(3) 0.108(6) Uani 1 1 d . . . H2A H 0.0260 0.5829 0.7814 0.163 Uiso 1 1 calc R . . H2B H 0.1402 0.5472 0.6132 0.163 Uiso 1 1 calc R . . H2C H 0.1876 0.6341 0.7631 0.163 Uiso 1 1 calc R . . C3 C 0.528(2) 0.2277(8) 0.788(2) 0.074(4) Uani 1 1 d . . . H3A H 0.5437 0.2616 0.9411 0.111 Uiso 1 1 calc R . . H3B H 0.6092 0.1816 0.8192 0.111 Uiso 1 1 calc R . . H3C H 0.4151 0.2043 0.7403 0.111 Uiso 1 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 Sn 0.0518(8) 0.0360(8) 0.0251(6) 0.0033(4) 0.0213(5) 0.0074(4) P 0.0522(17) 0.0321(15) 0.0225(12) 0.0005(10) 0.0168(11) -0.0014(13) O1 0.063(6) 0.067(6) 0.054(5) -0.012(4) 0.021(4) 0.003(4) O2 0.108(8) 0.060(6) 0.053(5) 0.026(4) 0.055(6) 0.012(5) O3 0.064(5) 0.051(6) 0.052(4) 0.011(4) 0.030(4) 0.010(4) C1 0.052(8) 0.063(7) 0.051(7) 0.002(6) 0.024(6) 0.017(6) C2 0.079(12) 0.143(18) 0.100(12) 0.033(12) 0.019(10) 0.029(11) C3 0.123(13) 0.062(9) 0.043(7) 0.026(6) 0.033(8) 0.022(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 Sn C1 2.136(12) 3_667 ? Sn C1 2.136(12) . ? Sn O2 2.197(7) 3_666 ? Sn O2 2.197(7) 1_556 ? Sn O1 2.230(9) 3_667 ? Sn O1 2.230(9) . ? P O2 1.477(7) . ? P O1 1.482(8) . ? P O3 1.559(10) . ? O2 Sn 2.197(7) 1_554 ? O3 C3 1.433(12) . ? C1 C2 1.48(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? 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 C1 Sn C1 180.000(2) 3_667 . ? C1 Sn O2 88.0(4) 3_667 3_666 ? C1 Sn O2 92.0(4) . 3_666 ? C1 Sn O2 92.0(4) 3_667 1_556 ? C1 Sn O2 88.0(4) . 1_556 ? O2 Sn O2 180.0(3) 3_666 1_556 ? C1 Sn O1 87.0(4) 3_667 3_667 ? C1 Sn O1 93.0(4) . 3_667 ? O2 Sn O1 87.9(4) 3_666 3_667 ? O2 Sn O1 92.1(4) 1_556 3_667 ? C1 Sn O1 93.0(4) 3_667 . ? C1 Sn O1 87.0(4) . . ? O2 Sn O1 92.1(4) 3_666 . ? O2 Sn O1 87.9(4) 1_556 . ? O1 Sn O1 180.0(4) 3_667 . ? O2 P O1 119.4(6) . . ? O2 P O3 105.7(5) . . ? O1 P O3 112.3(5) . . ? P O1 Sn 147.1(6) . . ? P O2 Sn 151.4(5) . 1_554 ? C3 O3 P 120.9(7) . . ? C2 C1 Sn 117.8(9) . . ? C2 C1 H1A 107.9 . . ? Sn C1 H1A 107.9 . . ? C2 C1 H1B 107.9 . . ? Sn C1 H1B 107.9 . . ? H1A C1 H1B 107.2 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O3 C3 H3A 109.5 . . ? O3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? O3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.851 _refine_diff_density_min -1.079 _refine_diff_density_rms 0.174 _database_code_depnum_ccdc_archive 'CCDC 903768' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_k13kcm14 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H14 O6 P2 Sn' _chemical_formula_sum 'C4 H14 O6 P2 Sn' _chemical_formula_weight 338.78 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' P P 0.1023 0.0942 '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' _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.1738(2) _cell_length_b 16.5102(5) _cell_length_c 6.4701(2) _cell_angle_alpha 90 _cell_angle_beta 92.1020(10) _cell_angle_gamma 90 _cell_volume 552.31(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16672 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 2.037 _exptl_crystal_F_000 332 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 2.600 _shelx_estimated_absorpt_T_min 0.624 _shelx_estimated_absorpt_T_max 0.781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.454 _exptl_absorpt_correction_T_max 0.603 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method '298 2.0 degree images with \f and \w scans' _diffrn_reflns_number 10164 _diffrn_reflns_av_unetI/netI 0.0225 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.003 _diffrn_reflns_theta_max 30.034 _reflns_number_total 1595 _reflns_number_gt 1428 _reflns_threshold_expression 'I > 2\s(I)' _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; DENZO-SCALEPACK Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press. ; _computing_structure_solution ; SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) J. Appl. Cryst. 32, 115-119 ; _computing_structure_refinement ; SHELXL-2012 (Sheldrick, 2012) Sheldrick GM (2008) Acta Crystallogr A64:112--122 and C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich ShelXle: a Qt graphical user interface for SHELXL J. Appl. Cryst., 44, (2011) 1281-1284. ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0224P)^2^+0.8845P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1595 _refine_ls_number_parameters 67 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0616 _refine_ls_wR_factor_gt 0.0594 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn Sn 0.5000 0.5000 0.5000 0.01446(8) Uani 1 2 d S . . P P -0.00943(12) 0.39648(4) 0.25259(10) 0.01747(13) Uani 1 1 d . . . H H -0.112(7) 0.402(2) 0.065(5) 0.029(9) Uiso 1 1 d . . . O1 O 0.2164(3) 0.45371(11) 0.2646(3) 0.0198(3) Uani 1 1 d . . . O2 O 0.0796(4) 0.30555(11) 0.2825(4) 0.0304(5) Uani 1 1 d . . . O3 O -0.2209(3) 0.40781(11) 0.4029(3) 0.0230(4) Uani 1 1 d . . . C1 C 0.6294(5) 0.58180(15) 0.2763(4) 0.0224(5) Uani 1 1 d . . . H1A H 0.8186 0.5851 0.2862 0.034 Uiso 1 1 calc R . . H1B H 0.5555 0.6355 0.3007 0.034 Uiso 1 1 calc R . . H1C H 0.5744 0.5628 0.1381 0.034 Uiso 1 1 calc R . . C2 C 0.3011(6) 0.27557(18) 0.1775(6) 0.0338(7) Uani 1 1 d . . . H2A H 0.4579 0.3020 0.2341 0.051 Uiso 1 1 calc R . . H2B H 0.2808 0.2875 0.0294 0.051 Uiso 1 1 calc R . . H2C H 0.3152 0.2169 0.1977 0.051 Uiso 1 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 Sn 0.01131(12) 0.01456(12) 0.01776(13) 0.00057(7) 0.00397(8) -0.00069(7) P 0.0141(3) 0.0186(3) 0.0200(3) -0.0027(2) 0.0031(2) -0.0019(2) O1 0.0173(8) 0.0209(8) 0.0214(9) -0.0008(7) 0.0018(7) -0.0041(6) O2 0.0278(10) 0.0186(9) 0.0460(13) -0.0027(8) 0.0188(9) 0.0004(7) O3 0.0175(8) 0.0217(9) 0.0302(10) -0.0006(7) 0.0078(7) 0.0020(7) C1 0.0220(12) 0.0230(12) 0.0225(13) 0.0062(9) 0.0050(10) -0.0022(9) C2 0.0268(14) 0.0247(13) 0.0511(19) -0.0077(12) 0.0164(13) 0.0011(11) _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 Sn C1 2.107(2) . ? Sn C1 2.107(2) 3_666 ? Sn O3 2.2053(17) 3_566 ? Sn O3 2.2053(17) 1_655 ? Sn O1 2.2117(18) 3_666 ? Sn O1 2.2117(18) . ? P O3 1.5019(18) . ? P O1 1.5025(18) . ? P O2 1.580(2) . ? P H 1.31(3) . ? O2 C2 1.441(3) . ? O3 Sn 2.2053(17) 1_455 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 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 C1 Sn C1 180.00(11) . 3_666 ? C1 Sn O3 88.92(9) . 3_566 ? C1 Sn O3 91.08(9) 3_666 3_566 ? C1 Sn O3 91.08(9) . 1_655 ? C1 Sn O3 88.92(9) 3_666 1_655 ? O3 Sn O3 180.0 3_566 1_655 ? C1 Sn O1 91.83(9) . 3_666 ? C1 Sn O1 88.17(9) 3_666 3_666 ? O3 Sn O1 89.44(7) 3_566 3_666 ? O3 Sn O1 90.56(7) 1_655 3_666 ? C1 Sn O1 88.17(9) . . ? C1 Sn O1 91.83(9) 3_666 . ? O3 Sn O1 90.56(7) 3_566 . ? O3 Sn O1 89.44(7) 1_655 . ? O1 Sn O1 180.00(8) 3_666 . ? O3 P O1 118.14(11) . . ? O3 P O2 104.78(11) . . ? O1 P O2 111.63(11) . . ? O3 P H 108.2(15) . . ? O1 P H 107.2(15) . . ? O2 P H 106.3(15) . . ? P O1 Sn 138.42(11) . . ? C2 O2 P 120.13(18) . . ? P O3 Sn 140.41(11) . 1_455 ? Sn C1 H1A 109.5 . . ? Sn C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Sn C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 H2A 109.5 . . ? O2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? O2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 2.272 _refine_diff_density_min -0.784 _refine_diff_density_rms 0.128 _database_code_depnum_ccdc_archive 'CCDC 952821'