# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Timothy Donohoe' 'Andrew Bell' 'Madeleine Helliwell' 'Lee Mitchell' 'Nicholas J. Newcombe' 'Michael J. Waring' _publ_contact_author_name 'Dr Timothy Donohoe' _publ_contact_author_address ; Chemistry University of Oxford Dyson Perrins Laboratory South Parks Road Oxford OXON OX1 3QY UNITED KINGDOM ; _publ_contact_author_email TIMOTHY.DONOHOE@CHEM.OX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Scope of the Directed Dihydroxylation: Application to Cyclic Homoallylic Alcohols and Trihaloacetamide ; data_S667 _database_code_CSD 207038 #------------------------------------------------------------------------------ _audit_creation_date 1998-06-16 _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; #------------------------------------------------------------------------------ loop_ _publ_manuscript_incl_extra_item '_geom_extra_table_head_3' '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' # # #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _cell_length_a 11.595(6) _cell_length_b 12.862(5) _cell_length_c 11.561(6) _cell_angle_alpha 101.31(4) _cell_angle_beta 119.63(3) _cell_angle_gamma 73.15(3) _cell_volume 1431(1) _cell_formula_units_Z 2 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #------------------------------------------------------------------------------ _exptl_crystal_description unknown _exptl_crystal_colour unknown _exptl_crystal_size_max 0.00 _exptl_crystal_size_mid 0.00 _exptl_crystal_size_min 0.00 _exptl_crystal_density_diffrn 1.749 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 753.98 _chemical_formula_analytical ? _chemical_formula_sum 'C19 H36 Cl5 N3 O5 Os ' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 744.00 _exptl_absorpt_coefficient_mu 4.950 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.799 _exptl_special_details ; The scan width was (0.00+0.00tan\q)\% with an \w scan speed of 0\% per minute . Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method ? _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -0.43 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 0 2 -3 2 2 -5 -2 3 _diffrn_reflns_number 5326 _reflns_number_total 5053 _reflns_number_observed 4202 _reflns_observed_criterion >2.00\s(I) _diffrn_reflns_av_R_equivalents 0.02308 _diffrn_reflns_av_sigmaI/netI 0.060 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.03506 _diffrn_orient_matrix_UB_12 -0.00776 _diffrn_orient_matrix_UB_13 0.06066 _diffrn_orient_matrix_UB_21 -0.03520 _diffrn_orient_matrix_UB_22 0.08066 _diffrn_orient_matrix_UB_23 0.00460 _diffrn_orient_matrix_UB_31 -0.08892 _diffrn_orient_matrix_UB_32 -0.00777 _diffrn_orient_matrix_UB_33 -0.07900 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 38 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 72 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 10 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N 0 6 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Cl 0 10 0.148 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Os 0 2 -1.216 7.603 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom Os(1) 0.15589(3) 0.15394(2) 0.32908(3) 0.02916(8) 1.000 . Uani d ? Cl(1) -0.1624(2) 0.5677(2) 0.0466(2) 0.0508(6) 1.000 . Uani d ? Cl(2) -0.0648(2) 0.7469(2) 0.0428(2) 0.0554(6) 1.000 . Uani d ? Cl(3) -0.1415(2) 0.7466(2) 0.2459(2) 0.0622(7) 1.000 . Uani d ? Cl(4) 0.4903(4) 0.0707(2) 0.8306(4) 0.126(1) 1.000 . Uani d ? Cl(5) 0.5011(4) -0.1555(3) 0.8339(3) 0.115(1) 1.000 . Uani d ? O(1) 0.1635(5) 0.1635(4) 0.4846(4) 0.040(1) 1.000 . Uani d ? O(2) 0.1142(5) 0.1177(4) 0.1621(5) 0.043(2) 1.000 . Uani d ? O(3) 0.3470(5) 0.1507(3) 0.3933(5) 0.037(1) 1.000 . Uani d ? O(4) 0.1276(5) 0.3101(3) 0.3167(4) 0.035(1) 1.000 . Uani d ? O(5) 0.1652(5) 0.6718(4) 0.3000(6) 0.059(2) 1.000 . Uani d ? N(1) 0.1838(6) -0.0228(4) 0.3428(6) 0.038(2) 1.000 . Uani d ? N(2) -0.0635(6) 0.1547(5) 0.2553(6) 0.040(2) 1.000 . Uani d ? N(3) 0.1097(6) 0.5111(4) 0.2715(5) 0.035(2) 1.000 . Uani d ? C(1) 0.2971(8) -0.0594(6) 0.4748(8) 0.057(3) 1.000 . Uani d ? C(2) 0.2119(9) -0.0932(6) 0.2373(9) 0.059(3) 1.000 . Uani d ? C(3) 0.0527(9) -0.0324(6) 0.3313(9) 0.054(3) 1.000 . Uani d ? C(4) -0.0679(8) 0.0359(6) 0.2262(9) 0.053(3) 1.000 . Uani d ? C(5) -0.1116(8) 0.2068(7) 0.3550(9) 0.063(3) 1.000 . Uani d ? C(6) -0.1548(8) 0.2114(7) 0.1304(9) 0.063(3) 1.000 . Uani d ? C(7) 0.3719(7) 0.2586(5) 0.4272(7) 0.032(2) 1.000 . Uani d ? C(8) 0.2476(7) 0.3314(5) 0.3270(6) 0.030(2) 1.000 . Uani d ? C(9) 0.2438(7) 0.4525(5) 0.3649(6) 0.033(2) 1.000 . Uani d ? C(10) 0.2723(7) 0.4818(5) 0.5094(7) 0.034(2) 1.000 . Uani d ? C(11) 0.4121(7) 0.4141(5) 0.6025(6) 0.031(2) 1.000 . Uani d ? C(12) 0.4055(7) 0.2939(5) 0.5697(6) 0.034(2) 1.000 . Uani d ? C(13) 0.0844(7) 0.6146(6) 0.2477(7) 0.037(2) 1.000 . Uani d ? C(14) -0.0647(7) 0.6653(5) 0.1475(6) 0.035(2) 1.000 . Uani d ? C(15) 0.4599(7) 0.4517(5) 0.7518(7) 0.036(2) 1.000 . Uani d ? C(16) 0.4752(8) 0.5692(6) 0.7772(7) 0.051(2) 1.000 . Uani d ? C(17) 0.3589(9) 0.4444(7) 0.7975(8) 0.064(3) 1.000 . Uani d ? C(18) 0.5987(9) 0.3799(6) 0.8375(7) 0.059(3) 1.000 . Uani d ? C(19) 0.5905(10) -0.0566(8) 0.866(1) 0.081(4) 1.000 . Uani d ? H(1a) 0.3010 -0.1342 0.4810 0.068 1.000 . Uiso c ? H(1b) 0.3812 -0.0558 0.4823 0.068 1.000 . Uiso c ? H(1c) 0.2824 -0.0163 0.5438 0.068 1.000 . Uiso c ? H(2a) 0.2183 -0.1681 0.2466 0.071 1.000 . Uiso c ? H(2b) 0.1408 -0.0733 0.1520 0.071 1.000 . Uiso c ? H(2c) 0.2961 -0.0883 0.2463 0.071 1.000 . Uiso c ? H(3a) 0.0459 -0.1063 0.3085 0.065 1.000 . Uiso c ? H(3b) 0.0535 -0.0104 0.4150 0.065 1.000 . Uiso c ? H(3n) 0.034(5) 0.482(4) 0.237(5) 0.02(1) 1.000 . Uiso d ? H(4a) -0.1490 0.0293 0.2229 0.064 1.000 . Uiso c ? H(4b) -0.0699 0.0143 0.1427 0.064 1.000 . Uiso c ? H(5c) -0.2038 0.2050 0.3223 0.075 1.000 . Uiso c ? H(5a) -0.0561 0.1739 0.4362 0.075 1.000 . Uiso c ? H(5b) -0.1074 0.2840 0.3714 0.075 1.000 . Uiso c ? H(6c) -0.2472 0.2104 0.1007 0.076 1.000 . Uiso c ? H(6a) -0.1504 0.2888 0.1478 0.076 1.000 . Uiso c ? H(6b) -0.1291 0.1818 0.0642 0.076 1.000 . Uiso c ? H(7) 0.4472 0.2604 0.4159 0.039 1.000 . Uiso c ? H(8) 0.2456 0.3166 0.2427 0.035 1.000 . Uiso c ? H(9) 0.3110 0.4712 0.3535 0.037 1.000 . Uiso c ? H(10b) 0.2038 0.4662 0.5216 0.040 1.000 . Uiso c ? H(10a) 0.2713 0.5574 0.5300 0.040 1.000 . Uiso c ? H(11) 0.4768 0.4251 0.5802 0.036 1.000 . Uiso c ? H(12a) 0.3373 0.2846 0.5866 0.040 1.000 . Uiso c ? H(12b) 0.4912 0.2520 0.6260 0.040 1.000 . Uiso c ? H(16b) 0.5403 0.5734 0.7519 0.059 1.000 . Uiso c ? H(16c) 0.3903 0.6150 0.7258 0.059 1.000 . Uiso c ? H(16a) 0.5060 0.5898 0.8690 0.059 1.000 . Uiso c ? H(17b) 0.2723 0.4920 0.7468 0.075 1.000 . Uiso c ? H(17c) 0.3483 0.3729 0.7836 0.075 1.000 . Uiso c ? H(17a) 0.3910 0.4684 0.8890 0.075 1.000 . Uiso c ? H(18b) 0.6623 0.3875 0.8125 0.071 1.000 . Uiso c ? H(18c) 0.6263 0.4058 0.9286 0.071 1.000 . Uiso c ? H(18a) 0.5912 0.3081 0.8249 0.071 1.000 . Uiso c ? H(19b) 0.6549 -0.0567 0.9576 0.096 1.000 . Uiso c ? H(19a) 0.6365 -0.0770 0.8133 0.096 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Os(1) 0.0330(2) 0.0215(1) 0.0312(2) -0.0054(1) 0.0132(1) 0.0006(1) Cl(1) 0.047(1) 0.051(1) 0.049(1) -0.0242(10) 0.0093(10) 0.0023(10) Cl(2) 0.063(1) 0.056(1) 0.046(1) -0.022(1) 0.011(1) 0.021(1) Cl(3) 0.065(1) 0.054(1) 0.085(2) -0.017(1) 0.049(1) -0.014(1) Cl(4) 0.156(3) 0.078(2) 0.155(3) 0.002(2) 0.091(3) 0.005(2) Cl(5) 0.159(3) 0.115(3) 0.122(3) -0.075(2) 0.086(2) -0.021(2) O(1) 0.048(3) 0.035(3) 0.036(3) -0.005(2) 0.021(3) -0.001(2) O(2) 0.057(3) 0.036(3) 0.039(3) -0.016(3) 0.020(3) 0.005(2) O(3) 0.036(3) 0.021(2) 0.050(3) -0.006(2) 0.018(2) -0.003(2) O(4) 0.041(3) 0.019(2) 0.042(3) -0.005(2) 0.015(2) 0.001(2) O(5) 0.044(3) 0.040(3) 0.082(4) -0.020(3) 0.003(3) 0.025(3) N(1) 0.051(4) 0.023(3) 0.039(4) -0.009(3) 0.019(3) 0.005(3) N(2) 0.033(4) 0.035(4) 0.049(4) -0.005(3) 0.015(3) 0.007(3) N(3) 0.043(4) 0.030(3) 0.032(3) -0.021(3) 0.007(3) 0.005(3) C(1) 0.054(6) 0.041(5) 0.063(6) 0.007(4) 0.018(5) 0.021(4) C(2) 0.088(7) 0.024(4) 0.082(6) -0.009(4) 0.055(6) -0.009(4) C(3) 0.057(6) 0.032(5) 0.081(7) -0.015(4) 0.029(5) 0.012(4) C(4) 0.039(5) 0.043(5) 0.083(7) -0.021(4) 0.025(5) -0.001(5) C(5) 0.049(5) 0.069(6) 0.081(7) -0.002(5) 0.043(5) -0.006(5) C(6) 0.039(5) 0.069(6) 0.068(6) -0.003(4) 0.010(5) 0.022(5) C(7) 0.026(4) 0.028(4) 0.037(4) -0.001(3) 0.015(3) -0.002(3) C(8) 0.037(4) 0.025(4) 0.031(4) -0.007(3) 0.019(3) 0.001(3) C(9) 0.038(4) 0.028(4) 0.035(4) -0.013(3) 0.013(3) 0.005(3) C(10) 0.037(4) 0.031(4) 0.035(4) -0.007(3) 0.019(3) -0.002(3) C(11) 0.034(4) 0.029(4) 0.034(4) -0.007(3) 0.017(3) 0.002(3) C(12) 0.027(4) 0.030(4) 0.033(4) -0.005(3) 0.007(3) -0.002(3) C(13) 0.041(4) 0.037(4) 0.036(4) -0.013(4) 0.014(4) 0.009(3) C(14) 0.041(4) 0.031(4) 0.034(4) -0.016(3) 0.016(4) -0.005(3) C(15) 0.034(4) 0.036(4) 0.033(4) -0.006(3) 0.012(3) 0.000(3) C(16) 0.049(5) 0.047(5) 0.044(5) -0.014(4) 0.012(4) -0.008(4) C(17) 0.083(7) 0.087(7) 0.042(5) -0.047(6) 0.036(5) -0.021(5) C(18) 0.061(6) 0.053(5) 0.035(5) -0.005(4) 0.006(4) -0.003(4) C(19) 0.068(7) 0.082(7) 0.108(8) -0.014(6) 0.054(7) -0.009(6) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00003|Fo|^2^]' _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.00000041(3) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 4202 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_obs 0.0354 _refine_ls_wR_factor_all 0.0369 _refine_ls_wR_factor_obs 0.0316 _refine_ls_goodness_of_fit_all 1.609 _refine_ls_goodness_of_fit_obs 1.521 _refine_ls_shift/esd_max 0.0000 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_min -0.79 _refine_diff_density_max 0.82 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Os(1) O(1) 1.737(4) . . yes Os(1) O(2) 1.741(5) . . yes Os(1) O(3) 1.948(5) . . yes Os(1) O(4) 1.961(4) . . yes Os(1) N(1) 2.227(5) . . yes Os(1) N(2) 2.246(6) . . yes Cl(1) C(14) 1.779(6) . . yes Cl(2) C(14) 1.750(7) . . yes Cl(3) C(14) 1.782(7) . . yes Cl(4) C(19) 1.699(10) . . yes Cl(5) C(19) 1.741(10) . . yes O(3) C(7) 1.438(7) . . yes O(4) C(8) 1.438(8) . . yes O(5) C(13) 1.204(7) . . yes N(1) C(1) 1.489(9) . . yes N(1) C(2) 1.485(9) . . yes N(1) C(3) 1.500(10) . . yes N(2) C(4) 1.510(9) . . yes N(2) C(5) 1.485(10) . . yes N(2) C(6) 1.480(9) . . yes N(3) C(9) 1.460(8) . . yes N(3) C(13) 1.331(8) . . yes N(3) H(3n) 0.93(5) . . no C(1) H(1a) 0.97 . . no C(1) H(1b) 0.95 . . no C(1) H(1c) 0.94 . . no C(2) H(2a) 0.97 . . no C(2) H(2b) 0.94 . . no C(2) H(2c) 0.95 . . no C(3) C(4) 1.49(1) . . yes C(3) H(3a) 0.95 . . no C(3) H(3b) 0.95 . . no C(4) H(4a) 0.95 . . no C(4) H(4b) 0.94 . . no C(5) H(5c) 0.95 . . no C(5) H(5a) 0.94 . . no C(5) H(5b) 0.98 . . no C(6) H(6c) 0.95 . . no C(6) H(6a) 0.99 . . no C(6) H(6b) 0.93 . . no C(7) C(8) 1.514(9) . . yes C(7) C(12) 1.498(9) . . yes C(7) H(7) 0.95 . . no C(8) C(9) 1.526(8) . . yes C(8) H(8) 0.95 . . no C(9) C(10) 1.523(9) . . yes C(9) H(9) 0.95 . . no C(10) C(11) 1.539(9) . . yes C(10) H(10b) 0.95 . . no C(10) H(10a) 0.95 . . no C(11) C(12) 1.533(8) . . yes C(11) C(15) 1.551(9) . . yes C(11) H(11) 0.96 . . no C(12) H(12a) 0.95 . . no C(12) H(12b) 0.94 . . no C(13) C(14) 1.555(9) . . yes C(15) C(16) 1.527(9) . . yes C(15) C(17) 1.53(1) . . yes C(15) C(18) 1.532(10) . . yes C(16) H(16b) 0.95 . . no C(16) H(16c) 0.94 . . no C(16) H(16a) 0.95 . . no C(17) H(17b) 0.96 . . no C(17) H(17c) 0.94 . . no C(17) H(17a) 0.95 . . no C(18) H(18b) 0.95 . . no C(18) H(18c) 0.96 . . no C(18) H(18a) 0.93 . . no C(19) H(19b) 0.95 . . no C(19) H(19a) 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(1) Os(1) O(2) 161.9(2) . . . yes O(1) Os(1) O(3) 96.8(2) . . . yes O(1) Os(1) O(4) 96.9(2) . . . yes O(1) Os(1) N(1) 82.7(2) . . . yes O(1) Os(1) N(2) 83.1(2) . . . yes O(2) Os(1) O(3) 97.4(2) . . . yes O(2) Os(1) O(4) 95.7(2) . . . yes O(2) Os(1) N(1) 84.5(2) . . . yes O(2) Os(1) N(2) 82.5(2) . . . yes O(3) Os(1) O(4) 84.6(2) . . . yes O(3) Os(1) N(1) 96.6(2) . . . yes O(3) Os(1) N(2) 179.1(2) . . . yes O(4) Os(1) N(1) 178.8(2) . . . yes O(4) Os(1) N(2) 96.4(2) . . . yes N(1) Os(1) N(2) 82.5(2) . . . yes Os(1) O(3) C(7) 111.5(4) . . . yes Os(1) O(4) C(8) 109.5(4) . . . yes Os(1) N(1) C(1) 110.8(4) . . . yes Os(1) N(1) C(2) 113.6(4) . . . yes Os(1) N(1) C(3) 104.6(4) . . . yes C(1) N(1) C(2) 108.2(6) . . . yes C(1) N(1) C(3) 108.9(6) . . . yes C(2) N(1) C(3) 110.6(6) . . . yes Os(1) N(2) C(4) 104.1(4) . . . yes Os(1) N(2) C(5) 112.4(5) . . . yes Os(1) N(2) C(6) 112.2(5) . . . yes C(4) N(2) C(5) 111.5(6) . . . yes C(4) N(2) C(6) 108.6(6) . . . yes C(5) N(2) C(6) 108.0(6) . . . yes C(9) N(3) C(13) 122.7(6) . . . yes C(9) N(3) H(3n) 120(3) . . . no C(13) N(3) H(3n) 115(3) . . . no N(1) C(1) H(1a) 108.8 . . . no N(1) C(1) H(1b) 109.8 . . . no N(1) C(1) H(1c) 110.3 . . . no H(1a) C(1) H(1b) 108.2 . . . no H(1a) C(1) H(1c) 109.2 . . . no H(1b) C(1) H(1c) 110.5 . . . no N(1) C(2) H(2a) 109.1 . . . no N(1) C(2) H(2b) 110.5 . . . no N(1) C(2) H(2c) 110.3 . . . no H(2a) C(2) H(2b) 108.6 . . . no H(2a) C(2) H(2c) 108.1 . . . no H(2b) C(2) H(2c) 110.2 . . . no N(1) C(3) C(4) 111.7(6) . . . yes N(1) C(3) H(3a) 108.8 . . . no N(1) C(3) H(3b) 108.7 . . . no C(4) C(3) H(3a) 108.5 . . . no C(4) C(3) H(3b) 109.7 . . . no H(3a) C(3) H(3b) 109.5 . . . no N(2) C(4) C(3) 111.5(6) . . . yes N(2) C(4) H(4a) 107.6 . . . no N(2) C(4) H(4b) 107.6 . . . no C(3) C(4) H(4a) 109.6 . . . no C(3) C(4) H(4b) 110.3 . . . no H(4a) C(4) H(4b) 110.2 . . . no N(2) C(5) H(5c) 110.9 . . . no N(2) C(5) H(5a) 111.0 . . . no N(2) C(5) H(5b) 109.2 . . . no H(5c) C(5) H(5a) 111.0 . . . no H(5c) C(5) H(5b) 106.9 . . . no H(5a) C(5) H(5b) 107.7 . . . no N(2) C(6) H(6c) 110.8 . . . no N(2) C(6) H(6a) 109.2 . . . no N(2) C(6) H(6b) 111.5 . . . no H(6c) C(6) H(6a) 106.2 . . . no H(6c) C(6) H(6b) 110.9 . . . no H(6a) C(6) H(6b) 108.0 . . . no O(3) C(7) C(8) 106.5(5) . . . yes O(3) C(7) C(12) 111.5(5) . . . yes O(3) C(7) H(7) 110.1 . . . no C(8) C(7) C(12) 114.2(6) . . . yes C(8) C(7) H(7) 107.0 . . . no C(12) C(7) H(7) 107.5 . . . no O(4) C(8) C(7) 108.8(5) . . . yes O(4) C(8) C(9) 108.1(5) . . . yes O(4) C(8) H(8) 109.3 . . . no C(7) C(8) C(9) 113.3(5) . . . yes C(7) C(8) H(8) 109.8 . . . no C(9) C(8) H(8) 107.5 . . . no N(3) C(9) C(8) 106.6(5) . . . yes N(3) C(9) C(10) 112.2(6) . . . yes N(3) C(9) H(9) 108.4 . . . no C(8) C(9) C(10) 112.0(5) . . . yes C(8) C(9) H(9) 109.2 . . . no C(10) C(9) H(9) 108.3 . . . no C(9) C(10) C(11) 109.7(6) . . . yes C(9) C(10) H(10b) 109.3 . . . no C(9) C(10) H(10a) 109.6 . . . no C(11) C(10) H(10b) 109.2 . . . no C(11) C(10) H(10a) 109.8 . . . no H(10b) C(10) H(10a) 109.2 . . . no C(10) C(11) C(12) 107.6(5) . . . yes C(10) C(11) C(15) 113.1(6) . . . yes C(10) C(11) H(11) 106.9 . . . no C(12) C(11) C(15) 114.2(5) . . . yes C(12) C(11) H(11) 108.0 . . . no C(15) C(11) H(11) 106.7 . . . no C(7) C(12) C(11) 112.4(5) . . . yes C(7) C(12) H(12a) 109.4 . . . no C(7) C(12) H(12b) 109.2 . . . no C(11) C(12) H(12a) 107.6 . . . no C(11) C(12) H(12b) 107.9 . . . no H(12a) C(12) H(12b) 110.3 . . . no O(5) C(13) N(3) 125.6(7) . . . yes O(5) C(13) C(14) 118.3(6) . . . yes N(3) C(13) C(14) 116.0(6) . . . yes Cl(1) C(14) Cl(2) 108.4(4) . . . yes Cl(1) C(14) Cl(3) 108.5(4) . . . yes Cl(1) C(14) C(13) 114.0(5) . . . yes Cl(2) C(14) Cl(3) 110.0(4) . . . yes Cl(2) C(14) C(13) 109.8(5) . . . yes Cl(3) C(14) C(13) 106.0(5) . . . yes C(11) C(15) C(16) 110.6(6) . . . yes C(11) C(15) C(17) 111.6(6) . . . yes C(11) C(15) C(18) 109.8(6) . . . yes C(16) C(15) C(17) 108.4(6) . . . yes C(16) C(15) C(18) 108.0(6) . . . yes C(17) C(15) C(18) 108.3(6) . . . yes C(15) C(16) H(16b) 108.6 . . . no C(15) C(16) H(16c) 109.4 . . . no C(15) C(16) H(16a) 109.0 . . . no H(16b) C(16) H(16c) 109.8 . . . no H(16b) C(16) H(16a) 109.7 . . . no H(16c) C(16) H(16a) 110.4 . . . no C(15) C(17) H(17b) 108.8 . . . no C(15) C(17) H(17c) 110.1 . . . no C(15) C(17) H(17a) 109.4 . . . no H(17b) C(17) H(17c) 109.5 . . . no H(17b) C(17) H(17a) 108.3 . . . no H(17c) C(17) H(17a) 110.7 . . . no C(15) C(18) H(18b) 108.3 . . . no C(15) C(18) H(18c) 107.9 . . . no C(15) C(18) H(18a) 109.4 . . . no H(18b) C(18) H(18c) 109.0 . . . no H(18b) C(18) H(18a) 111.3 . . . no H(18c) C(18) H(18a) 110.8 . . . no Cl(4) C(19) Cl(5) 113.8(6) . . . yes Cl(4) C(19) H(19b) 109.1 . . . no Cl(4) C(19) H(19a) 109.3 . . . no Cl(5) C(19) H(19b) 107.3 . . . no Cl(5) C(19) H(19a) 107.6 . . . no H(19b) C(19) H(19a) 109.8 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl(1) C(17) 3.584(9) . 2_566 no Cl(2) O(2) 2.944(5) . 2_565 no Cl(3) O(1) 3.212(5) . 2_566 no Cl(5) C(16) 3.546(8) . 1_545 no O(2) C(19) 3.45(1) . 2_656 no O(3) C(19) 3.34(1) . 2_656 no O(3) C(1) 3.522(9) . 2_656 no O(5) C(2) 3.486(9) . 1_565 no #------------------------------------------------------------------------------ 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 Os(1) O(3) C(7) C(8) . . . . -36.0(6) no Os(1) O(3) C(7) C(12) . . . . 89.1(5) no Os(1) O(4) C(8) C(7) . . . . -37.4(6) no Os(1) O(4) C(8) C(9) . . . . -160.8(4) no Os(1) N(1) C(3) C(4) . . . . 42.2(7) no Os(1) N(2) C(4) C(3) . . . . 41.1(7) no Cl(1) C(14) C(13) O(5) . . . . 165.0(6) no Cl(1) C(14) C(13) N(3) . . . . -17.3(8) no Cl(2) C(14) C(13) O(5) . . . . 43.1(9) no Cl(2) C(14) C(13) N(3) . . . . -139.2(5) no Cl(3) C(14) C(13) O(5) . . . . -75.7(8) no Cl(3) C(14) C(13) N(3) . . . . 102.0(6) no O(1) Os(1) O(3) C(7) . . . . -83.0(4) no O(1) Os(1) O(4) C(8) . . . . 110.4(4) no O(1) Os(1) N(1) C(1) . . . . -47.7(5) no O(1) Os(1) N(1) C(2) . . . . -169.8(5) no O(1) Os(1) N(1) C(3) . . . . 69.5(5) no O(1) Os(1) N(2) C(4) . . . . -97.0(5) no O(1) Os(1) N(2) C(5) . . . . 23.8(5) no O(1) Os(1) N(2) C(6) . . . . 145.7(5) no O(2) Os(1) O(3) C(7) . . . . 108.4(4) no O(2) Os(1) O(4) C(8) . . . . -82.8(4) no O(2) Os(1) N(1) C(1) . . . . 145.2(5) no O(2) Os(1) N(1) C(2) . . . . 23.1(5) no O(2) Os(1) N(1) C(3) . . . . -97.6(5) no O(2) Os(1) N(2) C(4) . . . . 71.9(5) no O(2) Os(1) N(2) C(5) . . . . -167.3(5) no O(2) Os(1) N(2) C(6) . . . . -45.4(5) no O(3) Os(1) O(4) C(8) . . . . 14.1(4) no O(3) Os(1) N(1) C(1) . . . . 48.4(5) no O(3) Os(1) N(1) C(2) . . . . -73.7(5) no O(3) Os(1) N(1) C(3) . . . . 165.6(5) no O(3) Os(1) N(2) C(4) . . . . -11(14) no O(3) Os(1) N(2) C(5) . . . . 109(13) no O(3) Os(1) N(2) C(6) . . . . -128(13) no O(3) C(7) C(8) O(4) . . . . 47.9(6) no O(3) C(7) C(8) C(9) . . . . 168.1(5) no O(3) C(7) C(12) C(11) . . . . -171.7(5) no O(4) Os(1) O(3) C(7) . . . . 13.3(4) no O(4) Os(1) N(1) C(1) . . . . -117(10) no O(4) Os(1) N(1) C(2) . . . . 120(10) no O(4) Os(1) N(1) C(3) . . . . 0(10) no O(4) Os(1) N(2) C(4) . . . . 166.8(5) no O(4) Os(1) N(2) C(5) . . . . -72.4(5) no O(4) Os(1) N(2) C(6) . . . . 49.5(5) no O(4) C(8) C(7) C(12) . . . . -75.6(7) no O(4) C(8) C(9) N(3) . . . . -50.6(7) no O(4) C(8) C(9) C(10) . . . . 72.5(7) no O(5) C(13) N(3) C(9) . . . . -1(1) no N(1) Os(1) O(3) C(7) . . . . -166.4(4) no N(1) Os(1) O(4) C(8) . . . . 179(10) no N(1) Os(1) N(2) C(4) . . . . -13.5(5) no N(1) Os(1) N(2) C(5) . . . . 107.3(5) no N(1) Os(1) N(2) C(6) . . . . -130.8(5) no N(1) C(3) C(4) N(2) . . . . -59.7(9) no N(2) Os(1) O(3) C(7) . . . . -168(13) no N(2) Os(1) O(4) C(8) . . . . -165.8(4) no N(2) Os(1) N(1) C(1) . . . . -131.7(5) no N(2) Os(1) N(1) C(2) . . . . 106.3(5) no N(2) Os(1) N(1) C(3) . . . . -14.5(5) no N(3) C(9) C(8) C(7) . . . . -171.2(5) no N(3) C(9) C(10) C(11) . . . . 177.7(5) no C(1) N(1) C(3) C(4) . . . . 160.7(6) no C(2) N(1) C(3) C(4) . . . . -80.5(8) no C(3) C(4) N(2) C(5) . . . . -80.3(8) no C(3) C(4) N(2) C(6) . . . . 160.8(7) no C(7) C(8) C(9) C(10) . . . . -48.2(8) no C(7) C(12) C(11) C(10) . . . . 59.1(7) no C(7) C(12) C(11) C(15) . . . . -174.5(6) no C(8) C(7) C(12) C(11) . . . . -51.0(8) no C(8) C(9) N(3) C(13) . . . . -158.9(6) no C(8) C(9) C(10) C(11) . . . . 57.9(7) no C(9) N(3) C(13) C(14) . . . . -178.8(6) no C(9) C(8) C(7) C(12) . . . . 44.6(8) no C(9) C(10) C(11) C(12) . . . . -62.3(7) no C(9) C(10) C(11) C(15) . . . . 170.7(5) no C(10) C(9) N(3) C(13) . . . . 78.1(8) no C(10) C(11) C(15) C(16) . . . . -61.4(7) no C(10) C(11) C(15) C(17) . . . . 59.4(8) no C(10) C(11) C(15) C(18) . . . . 179.5(6) no C(12) C(11) C(15) C(16) . . . . 175.1(6) no C(12) C(11) C(15) C(17) . . . . -64.1(8) no C(12) C(11) C(15) C(18) . . . . 56.0(8) no #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_d _geom_bond_atom_site_label_h _geom_contact_atom_site_label_a _geom_bond_distance_dh _geom_contact_distance_ha _geom_contact_distance_da _geom_angle_dha _geom_contact_site_symmetry_a N(3) H(3n) O(4) 0.93 2.30 2.667(7) 102.7 . N(3) H(3n) Cl(1) 0.93 2.41 2.923(6) 114.7 . data_s893 _database_code_CSD 207039 #------------------------------------------------------------------------------ _audit_creation_date 19100-10-03 _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _publ_section_exptl_refinement ; The data were collected using the RAXIS in 90 x 3 degree phi oscillations, of 5 minutes per exposure. The structure was solved by direct methods. The non-H atoms, were refined anisotropically, whilst H atoms were included in calculated positions. Possible H bonding interactions are as follows: Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and <DHA > 110 deg. D-H d(D-H) d(H..A) <DHA d(D..A) A N1-H1 0.860 2.182 161.59 3.010 O4 N1-H1 0.860 2.575 111.56 2.999 Cl1 ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H24 Cl3 N3 O5 Os' _chemical_formula_weight 598.90 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' N N 0.0061 0.0033 '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' Os Os -1.2165 7.6030 '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/c ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.19(2) _cell_length_b 11.405(10) _cell_length_c 15.857(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.57(4) _cell_angle_gamma 90.00 _cell_volume 1976(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 49058 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 26.36 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.013 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 6.888 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku RAXIS' _diffrn_measurement_method '90 x 3 degree phi scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 49058 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.36 _reflns_number_total 3844 _reflns_number_gt 3605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'DENZO (Otwinowski, Z. 1988)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'teXsan (MSC, 1995)' _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 w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+2.5867P] 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 3844 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0629 _refine_ls_wR_factor_gt 0.0619 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 Os1 Os 0.725220(11) -0.178723(11) 0.310098(8) 0.02275(7) Uani 1 d . . . Cl1 Cl 1.07904(9) -0.37751(8) 0.47309(6) 0.0390(2) Uani 1 d . . . Cl2 Cl 1.33754(11) -0.33901(12) 0.51567(9) 0.0612(3) Uani 1 d . . . Cl3 Cl 1.17519(13) -0.16351(10) 0.56033(8) 0.0522(3) Uani 1 d . . . O1 O 0.8406(2) -0.0485(2) 0.33207(16) 0.0333(6) Uani 1 d . . . O2 O 0.7532(3) -0.1737(2) 0.19321(18) 0.0381(7) Uani 1 d . . . O3 O 1.2859(3) -0.1632(4) 0.3835(3) 0.0781(14) Uani 1 d . . . O4 O 0.8350(2) -0.2852(2) 0.34952(17) 0.0304(5) Uani 1 d . . . O5 O 0.5913(3) -0.0982(2) 0.28961(18) 0.0395(6) Uani 1 d . . . N1 N 1.0819(3) -0.1836(3) 0.3458(2) 0.0344(8) Uani 1 d . . . H1 H 1.0187 -0.2146 0.3593 0.041 Uiso 1 calc R . . N2 N 0.6902(3) -0.1928(3) 0.4437(2) 0.0291(7) Uani 1 d . . . N3 N 0.5979(3) -0.3312(2) 0.2878(2) 0.0300(7) Uani 1 d . . . C1 C 0.8772(4) -0.0052(3) 0.2564(2) 0.0327(8) Uani 1 d . . . H1' H 0.8356 0.0686 0.2366 0.039 Uiso 1 calc R . . C2 C 1.0158(4) 0.0103(3) 0.2772(2) 0.0356(9) Uani 1 d . . . H2A H 1.0444 0.0388 0.3358 0.043 Uiso 1 calc R . . H2B H 1.0406 0.0651 0.2375 0.043 Uiso 1 calc R . . C3 C 1.0667(3) -0.1126(3) 0.2669(2) 0.0330(8) Uani 1 d . . . H3 H 1.1457 -0.1055 0.2502 0.040 Uiso 1 calc R . . C4 C 0.9729(4) -0.1653(3) 0.1922(3) 0.0386(9) Uani 1 d . . . H4A H 0.9611 -0.2478 0.2028 0.046 Uiso 1 calc R . . H4B H 1.0013 -0.1582 0.1388 0.046 Uiso 1 calc R . . C5 C 0.8521(3) -0.0985(3) 0.1849(2) 0.0317(8) Uani 1 d . . . H5 H 0.8315 -0.0593 0.1287 0.038 Uiso 1 calc R . . C6 C 1.1908(4) -0.2005(3) 0.3962(3) 0.0342(8) Uani 1 d . . . C7 C 1.1942(3) -0.2692(3) 0.4822(2) 0.0330(8) Uani 1 d . . . C8 C 0.6433(4) -0.3142(3) 0.4476(3) 0.0418(10) Uani 1 d . . . H8A H 0.6079 -0.3223 0.4980 0.050 Uiso 1 calc R . . H8B H 0.7105 -0.3694 0.4532 0.050 Uiso 1 calc R . . C9 C 0.5469(4) -0.3421(4) 0.3665(3) 0.0415(10) Uani 1 d . . . H9A H 0.5169 -0.4213 0.3704 0.050 Uiso 1 calc R . . H9B H 0.4783 -0.2887 0.3622 0.050 Uiso 1 calc R . . C10 C 0.8068(4) -0.1787(4) 0.5097(3) 0.0454(11) Uani 1 d . . . H10A H 0.7921 -0.1942 0.5661 0.068 Uiso 1 calc R . . H10B H 0.8365 -0.1001 0.5077 0.068 Uiso 1 calc R . . H10C H 0.8666 -0.2329 0.4978 0.068 Uiso 1 calc R . . C11 C 0.6011(4) -0.1056(4) 0.4630(3) 0.0496(11) Uani 1 d . . . H11A H 0.5240 -0.1154 0.4229 0.074 Uiso 1 calc R . . H11B H 0.6315 -0.0279 0.4576 0.074 Uiso 1 calc R . . H11C H 0.5903 -0.1173 0.5208 0.074 Uiso 1 calc R . . C12 C 0.6611(4) -0.4412(3) 0.2715(3) 0.0466(11) Uani 1 d . . . H12A H 0.7192 -0.4634 0.3230 0.070 Uiso 1 calc R . . H12B H 0.7030 -0.4285 0.2255 0.070 Uiso 1 calc R . . H12C H 0.6018 -0.5026 0.2555 0.070 Uiso 1 calc R . . C13 C 0.4959(4) -0.3126(4) 0.2115(3) 0.0492(12) Uani 1 d . . . H13A H 0.4422 -0.3792 0.2043 0.074 Uiso 1 calc R . . H13B H 0.5286 -0.3031 0.1607 0.074 Uiso 1 calc R . . H13C H 0.4511 -0.2435 0.2201 0.074 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 Os1 0.02093(10) 0.02327(10) 0.02462(10) 0.00032(5) 0.00618(6) -0.00044(4) Cl1 0.0385(5) 0.0372(5) 0.0424(5) 0.0013(4) 0.0114(4) -0.0054(4) Cl2 0.0336(6) 0.0802(9) 0.0683(8) 0.0199(6) 0.0081(6) 0.0157(5) Cl3 0.0649(8) 0.0509(6) 0.0445(6) -0.0164(5) 0.0201(5) -0.0112(5) O1 0.0419(15) 0.0297(13) 0.0309(13) -0.0071(11) 0.0138(11) -0.0100(12) O2 0.0438(17) 0.0418(18) 0.0303(16) -0.0063(10) 0.0114(13) -0.0178(12) O3 0.0308(18) 0.124(4) 0.078(3) 0.047(2) 0.0069(18) -0.0166(19) O4 0.0196(12) 0.0307(13) 0.0418(14) -0.0017(12) 0.0089(10) 0.0012(10) O5 0.0374(15) 0.0360(14) 0.0432(15) 0.0057(12) 0.0048(12) 0.0089(12) N1 0.0259(16) 0.0426(19) 0.0373(18) 0.0109(13) 0.0126(14) -0.0030(13) N2 0.0242(16) 0.0381(17) 0.0269(16) 0.0036(12) 0.0095(13) 0.0013(12) N3 0.0208(15) 0.0285(16) 0.0397(18) -0.0034(13) 0.0043(13) -0.0036(11) C1 0.043(2) 0.0234(16) 0.0332(18) 0.0041(15) 0.0117(16) -0.0042(16) C2 0.046(2) 0.0282(18) 0.0347(19) -0.0011(15) 0.0124(17) -0.0165(17) C3 0.0326(19) 0.0359(19) 0.0335(19) 0.0018(16) 0.0139(15) -0.0086(16) C4 0.046(2) 0.038(2) 0.033(2) -0.0043(16) 0.0117(18) -0.0055(17) C5 0.040(2) 0.0313(18) 0.0243(17) 0.0040(15) 0.0073(15) -0.0080(16) C6 0.0263(19) 0.0395(19) 0.039(2) -0.0001(17) 0.0123(16) -0.0019(16) C7 0.0263(18) 0.040(2) 0.0332(19) -0.0036(17) 0.0079(15) -0.0004(16) C8 0.044(2) 0.045(2) 0.039(2) 0.0122(17) 0.0163(19) -0.0057(18) C9 0.030(2) 0.043(2) 0.055(3) 0.0041(19) 0.0167(19) -0.0092(17) C10 0.041(2) 0.067(3) 0.025(2) 0.0008(17) 0.0006(18) -0.0055(19) C11 0.048(3) 0.057(3) 0.051(3) -0.007(2) 0.027(2) 0.010(2) C12 0.029(2) 0.031(2) 0.078(3) -0.012(2) 0.009(2) -0.0061(17) C13 0.032(2) 0.056(3) 0.051(3) -0.004(2) -0.010(2) -0.0095(18) _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 Os1 O5 1.727(3) . ? Os1 O4 1.744(3) . ? Os1 O2 1.947(3) . ? Os1 O1 1.949(2) . ? Os1 N3 2.227(3) . ? Os1 N2 2.243(3) . ? Cl1 C7 1.768(4) . ? Cl2 C7 1.767(4) . ? Cl3 C7 1.774(4) . ? O1 C1 1.438(4) . ? O2 C5 1.429(4) . ? O3 C6 1.204(5) . ? N1 C6 1.318(5) . ? N1 C3 1.469(5) . ? N1 H1 0.8600 . ? N2 C11 1.486(5) . ? N2 C8 1.487(5) . ? N2 C10 1.492(5) . ? N3 C9 1.486(5) . ? N3 C12 1.490(5) . ? N3 C13 1.488(5) . ? C1 C2 1.524(5) . ? C1 C5 1.536(5) . ? C1 H1 0.9800 . ? C2 C3 1.534(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.526(5) . ? C3 H3 0.9800 . ? C4 C5 1.534(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5 0.9800 . ? C6 C7 1.565(5) . ? C8 C9 1.522(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 O5 Os1 O4 162.27(13) . . ? O5 Os1 O2 96.77(13) . . ? O4 Os1 O2 96.61(13) . . ? O5 Os1 O1 98.19(12) . . ? O4 Os1 O1 94.54(12) . . ? O2 Os1 O1 84.86(10) . . ? O5 Os1 N3 83.48(12) . . ? O4 Os1 N3 83.64(12) . . ? O2 Os1 N3 95.84(12) . . ? O1 Os1 N3 178.11(11) . . ? O5 Os1 N2 83.86(12) . . ? O4 Os1 N2 82.28(12) . . ? O2 Os1 N2 177.45(11) . . ? O1 Os1 N2 97.51(11) . . ? N3 Os1 N2 81.76(12) . . ? C1 O1 Os1 114.3(2) . . ? C5 O2 Os1 113.2(2) . . ? C6 N1 C3 121.2(3) . . ? C6 N1 H1 119.4 . . ? C3 N1 H1 119.4 . . ? C11 N2 C8 110.8(3) . . ? C11 N2 C10 107.9(3) . . ? C8 N2 C10 109.5(3) . . ? C11 N2 Os1 114.2(2) . . ? C8 N2 Os1 104.0(2) . . ? C10 N2 Os1 110.4(3) . . ? C9 N3 C12 111.1(3) . . ? C9 N3 C13 109.1(3) . . ? C12 N3 C13 106.7(3) . . ? C9 N3 Os1 106.4(2) . . ? C12 N3 Os1 112.0(2) . . ? C13 N3 Os1 111.6(2) . . ? O1 C1 C2 108.7(3) . . ? O1 C1 C5 109.7(3) . . ? C2 C1 C5 104.7(3) . . ? O1 C1 H1 111.2 . . ? C2 C1 H1 111.2 . . ? C5 C1 H1 111.2 . . ? C1 C2 C3 104.8(3) . . ? C1 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? C1 C2 H2B 110.8 . . ? C3 C2 H2B 110.8 . . ? H2A C2 H2B 108.9 . . ? N1 C3 C4 112.1(3) . . ? N1 C3 C2 112.9(3) . . ? C4 C3 C2 103.5(3) . . ? N1 C3 H3 109.4 . . ? C4 C3 H3 109.4 . . ? C2 C3 H3 109.4 . . ? C3 C4 C5 108.0(3) . . ? C3 C4 H4A 110.1 . . ? C5 C4 H4A 110.1 . . ? C3 C4 H4B 110.1 . . ? C5 C4 H4B 110.1 . . ? H4A C4 H4B 108.4 . . ? O2 C5 C4 112.5(3) . . ? O2 C5 C1 111.7(3) . . ? C4 C5 C1 105.8(3) . . ? O2 C5 H5 108.9 . . ? C4 C5 H5 108.9 . . ? C1 C5 H5 108.9 . . ? O3 C6 N1 125.5(4) . . ? O3 C6 C7 117.9(4) . . ? N1 C6 C7 116.5(3) . . ? C6 C7 Cl2 109.6(3) . . ? C6 C7 Cl1 113.6(3) . . ? Cl2 C7 Cl1 107.9(2) . . ? C6 C7 Cl3 106.5(3) . . ? Cl2 C7 Cl3 109.6(2) . . ? Cl1 C7 Cl3 109.6(2) . . ? N2 C8 C9 110.6(3) . . ? N2 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? N3 C9 C8 111.1(3) . . ? N3 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? N3 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 O5 Os1 O1 C1 -89.7(3) . . . . ? O4 Os1 O1 C1 102.7(2) . . . . ? O2 Os1 O1 C1 6.4(2) . . . . ? N3 Os1 O1 C1 118(3) . . . . ? N2 Os1 O1 C1 -174.5(2) . . . . ? O5 Os1 O2 C5 107.6(3) . . . . ? O4 Os1 O2 C5 -84.1(3) . . . . ? O1 Os1 O2 C5 9.9(3) . . . . ? N3 Os1 O2 C5 -168.3(3) . . . . ? N2 Os1 O2 C5 -148(2) . . . . ? O5 Os1 N2 C11 -17.1(3) . . . . ? O4 Os1 N2 C11 173.9(3) . . . . ? O2 Os1 N2 C11 -122(3) . . . . ? O1 Os1 N2 C11 80.3(3) . . . . ? N3 Os1 N2 C11 -101.4(3) . . . . ? O5 Os1 N2 C8 103.7(3) . . . . ? O4 Os1 N2 C8 -65.2(3) . . . . ? O2 Os1 N2 C8 -1(3) . . . . ? O1 Os1 N2 C8 -158.8(3) . . . . ? N3 Os1 N2 C8 19.4(3) . . . . ? O5 Os1 N2 C10 -138.9(3) . . . . ? O4 Os1 N2 C10 52.2(2) . . . . ? O2 Os1 N2 C10 117(3) . . . . ? O1 Os1 N2 C10 -41.4(3) . . . . ? N3 Os1 N2 C10 136.8(3) . . . . ? O5 Os1 N3 C9 -75.3(2) . . . . ? O4 Os1 N3 C9 92.5(2) . . . . ? O2 Os1 N3 C9 -171.4(2) . . . . ? O1 Os1 N3 C9 77(3) . . . . ? N2 Os1 N3 C9 9.4(2) . . . . ? O5 Os1 N3 C12 163.3(3) . . . . ? O4 Os1 N3 C12 -29.0(3) . . . . ? O2 Os1 N3 C12 67.1(3) . . . . ? O1 Os1 N3 C12 -44(3) . . . . ? N2 Os1 N3 C12 -112.0(3) . . . . ? O5 Os1 N3 C13 43.7(3) . . . . ? O4 Os1 N3 C13 -148.6(3) . . . . ? O2 Os1 N3 C13 -52.5(3) . . . . ? O1 Os1 N3 C13 -164(3) . . . . ? N2 Os1 N3 C13 128.4(3) . . . . ? Os1 O1 C1 C2 -133.9(2) . . . . ? Os1 O1 C1 C5 -19.9(4) . . . . ? O1 C1 C2 C3 82.0(3) . . . . ? C5 C1 C2 C3 -35.2(4) . . . . ? C6 N1 C3 C4 140.0(4) . . . . ? C6 N1 C3 C2 -103.5(4) . . . . ? C1 C2 C3 N1 -86.5(4) . . . . ? C1 C2 C3 C4 35.0(4) . . . . ? N1 C3 C4 C5 100.3(4) . . . . ? C2 C3 C4 C5 -21.7(4) . . . . ? Os1 O2 C5 C4 95.8(3) . . . . ? Os1 O2 C5 C1 -23.1(4) . . . . ? C3 C4 C5 O2 -121.8(3) . . . . ? C3 C4 C5 C1 0.4(4) . . . . ? O1 C1 C5 O2 27.6(4) . . . . ? C2 C1 C5 O2 144.1(3) . . . . ? O1 C1 C5 C4 -95.2(3) . . . . ? C2 C1 C5 C4 21.3(4) . . . . ? C3 N1 C6 O3 -1.2(7) . . . . ? C3 N1 C6 C7 175.2(3) . . . . ? O3 C6 C7 Cl2 -29.2(5) . . . . ? N1 C6 C7 Cl2 154.1(3) . . . . ? O3 C6 C7 Cl1 -150.0(4) . . . . ? N1 C6 C7 Cl1 33.3(4) . . . . ? O3 C6 C7 Cl3 89.2(5) . . . . ? N1 C6 C7 Cl3 -87.5(4) . . . . ? C11 N2 C8 C9 77.1(4) . . . . ? C10 N2 C8 C9 -164.0(4) . . . . ? Os1 N2 C8 C9 -46.0(4) . . . . ? C12 N3 C9 C8 84.6(4) . . . . ? C13 N3 C9 C8 -158.0(3) . . . . ? Os1 N3 C9 C8 -37.5(4) . . . . ? N2 C8 C9 N3 59.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 0.920 _refine_diff_density_min -1.444 _refine_diff_density_rms 0.115