# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Peng Cheng' _publ_contact_author_email pcheng@nankai.edu.cn _publ_author_name 'Peng Cheng' data_a _database_code_depnum_ccdc_archive 'CCDC 848323' #TrackingRef '- a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H8 Co N O5.50 S' _chemical_formula_weight 261.11 _chemical_absolute_configuration ad 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' Co Co 0.3494 0.9721 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z+1/4' '-x, -y, z+1/2' 'y, -x, z+3/4' _cell_length_a 12.367(3) _cell_length_b 12.367(3) _cell_length_c 5.2934(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 809.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1859 _cell_measurement_theta_min 3.29 _cell_measurement_theta_max 27.46 _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 2.373 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.5362 _exptl_absorpt_correction_T_max 0.7973 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8081 _diffrn_reflns_av_R_equivalents 0.1534 _diffrn_reflns_av_sigmaI/netI 0.1393 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1859 _reflns_number_gt 1390 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. It should be noted O5 and O6 atoms were treated by disorder and these atoms were refined anisotropically with application of restrains on thermal parameters (ISOR instructions in SHELXL). ; _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^)+(0.0309P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(5) _refine_ls_number_reflns 1859 _refine_ls_number_parameters 131 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1171 _refine_ls_R_factor_gt 0.0841 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 Co1 Co 0.67880(8) 1.01520(9) 0.5373(2) 0.0190(3) Uani 1 1 d . . . S1 S 0.56086(19) 0.69305(17) 0.4732(5) 0.0298(6) Uani 1 1 d . . . N1 N 0.6170(5) 0.8736(5) 0.7218(12) 0.0197(17) Uani 1 1 d . . . H5A H 0.8533 1.0243 0.8456 0.024 Uiso 1 1 d R . . H5B H 0.7504 1.0575 0.9480 0.024 Uiso 1 1 d R . . C5 C 0.6544(7) 0.6815(6) 0.7282(18) 0.026(2) Uani 1 1 d . . . H5C H 0.6177 0.6604 0.8824 0.03(3) Uiso 1 1 calc R . . H5D H 0.7097 0.6283 0.6901 0.007(19) Uiso 1 1 calc R . . C3 C 0.7037(6) 0.7935(6) 0.7549(18) 0.0194(19) Uani 1 1 d . . . H3 H 0.7339 0.8009 0.9251 0.02(2) Uiso 1 1 calc R . . C4 C 0.7933(6) 0.8134(7) 0.5609(17) 0.0197(19) Uani 1 1 d . . . C1 C 0.5260(7) 0.8311(6) 0.5689(17) 0.023(2) Uani 1 1 d . . . H1 H 0.4606 0.8291 0.6734 0.03(3) Uiso 1 1 calc R . . C2 C 0.5034(6) 0.8956(6) 0.3344(16) 0.0156(19) Uani 1 1 d . . . O4 O 0.8678(4) 0.7429(4) 0.5362(13) 0.0240(13) Uani 1 1 d . . . O3 O 0.7929(4) 0.8998(4) 0.4340(11) 0.0263(16) Uani 1 1 d . . . O2 O 0.5703(4) 0.9678(4) 0.2688(12) 0.0240(13) Uani 1 1 d . . . O1 O 0.4195(4) 0.8723(4) 0.2166(12) 0.0284(16) Uani 1 1 d . . . O5 O 0.7906(5) 1.0501(5) 0.8179(12) 0.0424(18) Uani 1 1 d U . . H6 H 0.5998 0.8773 0.8700 0.051 Uiso 1 1 d R . . O6 O 0.9888(15) 0.0015(16) 0.319(7) 0.080(5) Uani 0.50 1 d PU . . 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 Co1 0.0178(6) 0.0171(6) 0.0221(5) -0.0018(6) 0.0003(6) 0.0004(5) S1 0.0353(14) 0.0171(11) 0.0369(15) -0.0024(11) -0.0077(12) 0.0028(10) N1 0.021(4) 0.028(4) 0.010(4) -0.007(3) 0.007(3) 0.003(3) C5 0.031(5) 0.016(5) 0.032(6) 0.011(4) 0.002(5) 0.012(4) C3 0.016(4) 0.027(5) 0.016(5) 0.002(4) -0.007(4) 0.004(4) C4 0.015(4) 0.025(5) 0.019(5) -0.011(4) -0.010(4) 0.001(4) C1 0.027(5) 0.010(4) 0.031(5) 0.004(4) 0.000(5) 0.001(3) C2 0.016(4) 0.015(4) 0.016(5) -0.012(4) 0.001(4) 0.002(4) O4 0.020(3) 0.028(3) 0.024(3) 0.006(3) 0.010(3) 0.005(3) O3 0.018(3) 0.025(4) 0.036(4) 0.002(3) 0.001(3) 0.004(3) O2 0.027(3) 0.027(3) 0.018(3) 0.000(3) -0.001(3) 0.001(3) O1 0.023(3) 0.024(3) 0.038(4) 0.003(3) -0.012(3) 0.001(3) O5 0.026(3) 0.064(4) 0.037(4) -0.013(4) 0.002(3) 0.005(3) O6 0.068(8) 0.081(8) 0.091(10) -0.009(8) 0.015(8) 0.005(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 Co1 O2 2.041(6) . ? Co1 O5 2.075(6) . ? Co1 O1 2.077(5) 3_675 ? Co1 O3 2.080(6) . ? Co1 O4 2.119(6) 4_574 ? Co1 N1 2.146(6) . ? S1 C5 1.783(9) . ? S1 C1 1.832(7) . ? N1 C3 1.470(9) . ? N1 C1 1.483(11) . ? N1 H6 0.8139 . ? C5 C3 1.520(11) . ? C5 H5C 0.9700 . ? C5 H5D 0.9700 . ? C3 C4 1.532(12) . ? C3 H3 0.9800 . ? C4 O3 1.262(10) . ? C4 O4 1.275(8) . ? C1 C2 1.502(12) . ? C1 H1 0.9800 . ? C2 O1 1.244(9) . ? C2 O2 1.265(9) . ? O4 Co1 2.119(6) 2_755 ? O1 Co1 2.077(5) 3_674 ? O5 H5A 0.8508 . ? O5 H5B 0.8543 . ? O6 O6 1.338(4) 2_645 ? O6 O6 1.338(4) 4_664 ? 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 O2 Co1 O5 175.3(3) . . ? O2 Co1 O1 97.2(2) . 3_675 ? O5 Co1 O1 85.6(2) . 3_675 ? O2 Co1 O3 93.8(2) . . ? O5 Co1 O3 83.1(2) . . ? O1 Co1 O3 167.6(3) 3_675 . ? O2 Co1 O4 90.3(2) . 4_574 ? O5 Co1 O4 93.3(2) . 4_574 ? O1 Co1 O4 92.8(2) 3_675 4_574 ? O3 Co1 O4 92.8(2) . 4_574 ? O2 Co1 N1 81.3(2) . . ? O5 Co1 N1 94.7(3) . . ? O1 Co1 N1 97.5(2) 3_675 . ? O3 Co1 N1 78.5(2) . . ? O4 Co1 N1 167.4(2) 4_574 . ? C5 S1 C1 91.1(4) . . ? C3 N1 C1 112.3(6) . . ? C3 N1 Co1 110.1(5) . . ? C1 N1 Co1 108.1(5) . . ? C3 N1 H6 96.5 . . ? C1 N1 H6 110.3 . . ? Co1 N1 H6 119.1 . . ? C3 C5 S1 104.9(5) . . ? C3 C5 H5C 110.8 . . ? S1 C5 H5C 110.8 . . ? C3 C5 H5D 110.8 . . ? S1 C5 H5D 110.8 . . ? H5C C5 H5D 108.8 . . ? N1 C3 C5 108.1(6) . . ? N1 C3 C4 109.8(7) . . ? C5 C3 C4 112.0(7) . . ? N1 C3 H3 108.9 . . ? C5 C3 H3 108.9 . . ? C4 C3 H3 108.9 . . ? O3 C4 O4 121.9(8) . . ? O3 C4 C3 119.3(7) . . ? O4 C4 C3 118.8(8) . . ? N1 C1 C2 113.8(6) . . ? N1 C1 S1 107.6(5) . . ? C2 C1 S1 108.1(6) . . ? N1 C1 H1 109.1 . . ? C2 C1 H1 109.1 . . ? S1 C1 H1 109.1 . . ? O1 C2 O2 124.8(8) . . ? O1 C2 C1 116.5(7) . . ? O2 C2 C1 118.7(7) . . ? C4 O4 Co1 133.2(6) . 2_755 ? C4 O3 Co1 116.4(5) . . ? C2 O2 Co1 116.2(6) . . ? C2 O1 Co1 124.2(5) . 3_674 ? Co1 O5 H5A 130.7 . . ? Co1 O5 H5B 102.2 . . ? H5A O5 H5B 115.5 . . ? O6 O6 O6 168.0(15) 2_645 4_664 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.852 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.128 # Attachment 'c081018j-1D-298K.cif' data_b _database_code_depnum_ccdc_archive 'CCDC 848324' #TrackingRef '- a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H11 Co N O7 S' _chemical_formula_weight 288.14 _chemical_absolute_configuration ad 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.3211(11) _cell_length_b 9.6312(19) _cell_length_c 9.764(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.10(3) _cell_angle_gamma 90.00 _cell_volume 491.03(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2231 _cell_measurement_theta_min 3.90 _cell_measurement_theta_max 27.47 _exptl_crystal_description needle _exptl_crystal_colour pink _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.949 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 294 _exptl_absorpt_coefficient_mu 1.977 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9076 _exptl_absorpt_correction_T_max 0.9805 _exptl_absorpt_process_details ? _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5022 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.90 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2231 _reflns_number_gt 2032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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. It should be noted O5, O6, O7, H5a, H5b, H6a, H6b, H7a and H7b atoms were treated by disorder and these atoms were refined anisotropically with application of restrains on bond distence (DFIX instructions in SHELXL). ; _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^)+(0.0311P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(2) _refine_ls_number_reflns 2231 _refine_ls_number_parameters 136 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 Co1 Co 0.54513(9) 0.57573(5) 0.38537(5) 0.01949(13) Uani 1 1 d . . . S1 S 0.4256(2) 0.89621(12) 0.07634(12) 0.0373(3) Uani 1 1 d . . . N1 N 0.6870(6) 0.6976(3) 0.2354(3) 0.0195(7) Uani 1 1 d . . . H8 H 0.7863 0.6328 0.1882 0.023 Uiso 1 1 d R . . C1 C 0.4862(7) 0.7115(4) 0.1103(4) 0.0212(8) Uani 1 1 d . . . H1 H 0.5464 0.6700 0.0307 0.025 Uiso 1 1 calc R . . C2 C 0.2307(8) 0.6445(4) 0.1236(4) 0.0208(8) Uani 1 1 d . . . C3 C 0.7653(8) 0.8333(4) 0.2991(4) 0.0200(8) Uani 1 1 d . . . H3 H 0.9475 0.8293 0.3420 0.024 Uiso 1 1 calc R . . C4 C 0.6121(7) 0.8673(4) 0.4118(4) 0.0179(8) Uani 1 1 d . . . C5 C 0.7282(8) 0.9405(4) 0.1830(4) 0.0269(9) Uani 1 1 d . . . H5C H 0.8645 0.9349 0.1300 0.032 Uiso 1 1 calc R . . H5D H 0.7243 1.0336 0.2204 0.032 Uiso 1 1 calc R . . O1 O 0.0473(5) 0.6619(3) 0.0284(3) 0.0311(7) Uani 1 1 d . . . O2 O 0.2231(4) 0.5750(4) 0.2340(2) 0.0276(5) Uani 1 1 d . . . O3 O 0.4656(5) 0.7779(3) 0.4463(3) 0.0220(6) Uani 1 1 d . . . O4 O 0.6467(5) 0.9860(3) 0.4664(3) 0.0224(6) Uani 1 1 d . . . O5 O 0.8799(5) 0.5969(4) 0.5396(3) 0.0398(9) Uani 1 1 d . . . H5A H 1.0239 0.5594 0.5310 0.048 Uiso 1 1 d R . . H5B H 0.8648 0.6649 0.5958 0.048 Uiso 1 1 d R . . O6 O 0.6607(7) 0.3832(3) 0.3281(3) 0.0427(8) Uani 1 1 d . . . H6A H 0.5049 0.3800 0.2783 0.051 Uiso 1 1 d RD . . H6B H 0.7987 0.3605 0.2998 0.051 Uiso 1 1 d RD . . O7 O 0.0669(6) 0.2767(4) 0.2291(3) 0.0417(8) Uani 1 1 d . . . H7A H -0.0125 0.2487 0.1491 0.050 Uiso 1 1 d R . . H7B H 0.2266 0.2673 0.2650 0.050 Uiso 1 1 d 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 Co1 0.0243(2) 0.0151(2) 0.0202(2) 0.0007(2) 0.00697(17) 0.0009(3) S1 0.0503(7) 0.0242(6) 0.0329(6) 0.0087(5) -0.0030(5) -0.0046(5) N1 0.0199(17) 0.0159(16) 0.0243(18) -0.0042(13) 0.0081(13) 0.0027(13) C1 0.024(2) 0.022(2) 0.019(2) -0.0028(16) 0.0092(16) -0.0053(16) C2 0.025(2) 0.019(2) 0.020(2) -0.0083(16) 0.0094(17) -0.0019(16) C3 0.017(2) 0.020(2) 0.024(2) -0.0032(16) 0.0071(16) -0.0022(15) C4 0.0167(19) 0.017(2) 0.0193(19) 0.0005(15) 0.0022(15) 0.0014(15) C5 0.037(2) 0.024(2) 0.022(2) 0.0013(16) 0.0102(18) -0.0097(18) O1 0.0216(17) 0.046(2) 0.0235(17) 0.0024(14) 0.0001(13) -0.0045(13) O2 0.0253(13) 0.0328(14) 0.0253(13) 0.0038(18) 0.0064(10) -0.0078(19) O3 0.0276(16) 0.0131(13) 0.0283(16) 0.0004(11) 0.0131(12) -0.0032(11) O4 0.0286(16) 0.0189(15) 0.0222(14) -0.0059(11) 0.0108(12) -0.0050(11) O5 0.0294(15) 0.050(3) 0.0383(17) -0.0105(17) 0.0010(12) 0.0155(17) O6 0.062(2) 0.0279(18) 0.047(2) 0.0006(16) 0.0310(18) 0.0120(16) O7 0.044(2) 0.052(2) 0.0286(18) -0.0052(15) 0.0058(14) -0.0199(16) _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. It should be noted O5 and O6 atoms were treated by disorder and these atoms were refined anisotropically with application of restrains on thermal parameters (ISOR instructions in SHELXL). ; 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 Co1 O2 2.036(2) . ? Co1 O6 2.065(3) . ? Co1 O3 2.103(3) . ? Co1 O5 2.110(3) . ? Co1 O4 2.110(3) 2_646 ? Co1 N1 2.125(3) . ? S1 C5 1.793(4) . ? S1 C1 1.827(4) . ? N1 C1 1.466(5) . ? N1 C3 1.473(5) . ? C1 C2 1.533(5) . ? C2 O1 1.223(5) . ? C2 O2 1.276(5) . ? C3 C5 1.517(5) . ? C3 C4 1.526(5) . ? C4 O3 1.250(4) . ? C4 O4 1.260(4) . ? O4 Co1 2.110(3) 2_656 ? 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 O2 Co1 O6 93.04(15) . . ? O2 Co1 O3 91.25(13) . . ? O6 Co1 O3 174.31(13) . . ? O2 Co1 O5 174.61(18) . . ? O6 Co1 O5 91.47(14) . . ? O3 Co1 O5 84.06(12) . . ? O2 Co1 O4 92.62(10) . 2_646 ? O6 Co1 O4 91.52(11) . 2_646 ? O3 Co1 O4 92.02(10) . 2_646 ? O5 Co1 O4 90.21(12) . 2_646 ? O2 Co1 N1 82.11(12) . . ? O6 Co1 N1 98.37(12) . . ? O3 Co1 N1 78.52(11) . . ? O5 Co1 N1 94.32(13) . . ? O4 Co1 N1 169.00(11) 2_646 . ? C5 S1 C1 91.08(18) . . ? C1 N1 C3 111.9(3) . . ? C1 N1 Co1 109.1(2) . . ? C3 N1 Co1 108.0(2) . . ? N1 C1 C2 114.0(3) . . ? N1 C1 S1 108.4(2) . . ? C2 C1 S1 107.3(3) . . ? O1 C2 O2 124.3(4) . . ? O1 C2 C1 117.9(3) . . ? O2 C2 C1 117.8(3) . . ? N1 C3 C5 107.6(3) . . ? N1 C3 C4 110.3(3) . . ? C5 C3 C4 112.4(3) . . ? O3 C4 O4 123.9(3) . . ? O3 C4 C3 119.6(3) . . ? O4 C4 C3 116.4(3) . . ? C3 C5 S1 104.2(3) . . ? C2 O2 Co1 116.9(3) . . ? C4 O3 Co1 113.0(2) . . ? C4 O4 Co1 127.7(2) . 2_656 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.393 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.084 # Attachment '090205aa-3D-353K.cif' data_c _database_code_depnum_ccdc_archive 'CCDC 848325' #TrackingRef '- a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H8 Co N O5.50 S' _chemical_formula_weight 261.11 _chemical_absolute_configuration ad 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 12.2640(17) _cell_length_b 12.2640(17) _cell_length_c 5.2535(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 790.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1565 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 27.46 _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 2.431 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.5291 _exptl_absorpt_correction_T_max 0.7931 _exptl_absorpt_process_details ? _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4806 _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_sigmaI/netI 0.0968 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1565 _reflns_number_gt 1314 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0306P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 1565 _refine_ls_number_parameters 128 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.17871(6) 0.51530(6) 0.21753(16) 0.0129(2) Uani 1 1 d . . . S1 S 0.06093(14) 0.19272(13) 0.1529(4) 0.0234(4) Uani 1 1 d . . . N1 N 0.1159(4) 0.3736(3) 0.4019(10) 0.0133(12) Uani 1 1 d . . . H8 H 0.0909 0.3957 0.5267 0.016 Uiso 1 1 d R . . C1 C 0.0244(5) 0.3302(4) 0.2529(13) 0.0152(14) Uani 1 1 d . . . H1 H -0.0415 0.3279 0.3585 0.018 Uiso 1 1 calc R . . C2 C 0.0030(5) 0.3962(5) 0.0164(13) 0.0138(15) Uani 1 1 d . . . C3 C 0.2035(4) 0.2936(4) 0.4350(14) 0.0139(14) Uani 1 1 d . . . H3 H 0.2341 0.3024 0.6061 0.017 Uiso 1 1 calc R . . C4 C 0.2931(5) 0.3139(5) 0.2428(13) 0.0145(14) Uani 1 1 d . . . C5 C 0.1545(5) 0.1812(4) 0.4156(14) 0.0206(17) Uani 1 1 d . . . H5C H 0.1166 0.1617 0.5711 0.025 Uiso 1 1 calc R . . H5D H 0.2102 0.1270 0.3811 0.025 Uiso 1 1 calc R . . O1 O -0.0818(3) 0.3721(3) -0.1026(9) 0.0225(12) Uani 1 1 d . . . O2 O 0.0698(3) 0.4677(3) -0.0540(10) 0.0169(10) Uani 1 1 d . . . O3 O 0.2927(3) 0.3988(3) 0.1140(9) 0.0189(11) Uani 1 1 d . . . O4 O 0.3674(3) 0.2434(3) 0.2208(10) 0.0182(10) Uani 1 1 d . . . O5 O 0.2905(3) 0.5501(4) 0.5020(9) 0.0328(13) Uani 1 1 d . . . H5A H 0.2588 0.5775 0.6237 0.039 Uiso 1 1 calc R . . H5B H 0.3583 0.5399 0.4687 0.039 Uiso 1 1 d R . . O6 O 0.4872(18) 0.5046(13) 0.992(9) 0.108(9) Uani 0.50 1 d P . . 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 Co1 0.0114(4) 0.0121(4) 0.0150(4) -0.0020(4) 0.0007(4) 0.0002(4) S1 0.0283(10) 0.0125(8) 0.0294(11) -0.0024(8) -0.0070(8) 0.0032(7) N1 0.013(3) 0.015(3) 0.012(3) -0.002(2) -0.001(2) 0.004(2) C1 0.015(3) 0.012(3) 0.019(4) -0.002(3) -0.001(3) -0.002(3) C2 0.022(3) 0.007(3) 0.013(4) 0.001(3) -0.001(3) 0.005(3) C3 0.015(3) 0.019(3) 0.007(4) 0.003(3) -0.004(3) 0.003(3) C4 0.017(3) 0.017(3) 0.009(4) 0.001(3) -0.006(3) 0.001(3) C5 0.021(3) 0.016(3) 0.025(5) 0.009(3) 0.003(3) 0.004(3) O1 0.021(2) 0.017(2) 0.030(3) 0.001(2) -0.009(2) -0.002(2) O2 0.018(2) 0.017(2) 0.016(2) 0.008(2) -0.005(2) -0.0042(18) O3 0.016(2) 0.017(2) 0.023(3) 0.000(2) 0.005(2) 0.0078(19) O4 0.016(2) 0.020(2) 0.018(2) 0.003(2) 0.000(2) 0.0091(19) O5 0.019(2) 0.053(3) 0.027(3) -0.021(3) -0.004(2) 0.002(3) O6 0.097(13) 0.043(8) 0.18(3) 0.018(15) 0.098(17) 0.030(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. ; 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 Co1 O2 2.040(4) . ? Co1 O1 2.053(4) 2_565 ? Co1 O5 2.072(4) . ? Co1 O3 2.071(4) . ? Co1 O4 2.093(5) 4_564 ? Co1 N1 2.133(5) . ? S1 C5 1.800(7) . ? S1 C1 1.822(6) . ? N1 C1 1.468(8) . ? N1 C3 1.465(7) . ? C1 C2 1.506(9) . ? C2 O1 1.248(7) . ? C2 O2 1.255(7) . ? C3 C5 1.506(8) . ? C3 C4 1.514(9) . ? C4 O3 1.241(7) . ? C4 O4 1.261(6) . ? O1 Co1 2.053(4) 2_564 ? O4 Co1 2.093(4) 3_655 ? O6 O6 1.334(5) 4_564 ? O6 O6 1.334(5) 3_655 ? 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 O2 Co1 O1 97.77(17) . 2_565 ? O2 Co1 O5 175.20(18) . . ? O1 Co1 O5 85.00(18) 2_565 . ? O2 Co1 O3 93.48(17) . . ? O1 Co1 O3 167.4(2) 2_565 . ? O5 Co1 O3 83.39(18) . . ? O2 Co1 O4 90.70(18) . 4_564 ? O1 Co1 O4 92.41(17) 2_565 4_564 ? O5 Co1 O4 93.11(18) . 4_564 ? O3 Co1 O4 93.20(17) . 4_564 ? O2 Co1 N1 81.24(19) . . ? O1 Co1 N1 97.48(18) 2_565 . ? O5 Co1 N1 94.53(19) . . ? O3 Co1 N1 78.52(17) . . ? O4 Co1 N1 168.0(2) 4_564 . ? C5 S1 C1 90.5(3) . . ? C1 N1 C3 112.4(4) . . ? C1 N1 Co1 109.2(4) . . ? C3 N1 Co1 109.6(3) . . ? N1 C1 C2 112.2(5) . . ? N1 C1 S1 107.5(4) . . ? C2 C1 S1 107.6(4) . . ? O1 C2 O2 124.1(6) . . ? O1 C2 C1 115.5(6) . . ? O2 C2 C1 120.3(6) . . ? N1 C3 C5 108.2(4) . . ? N1 C3 C4 110.0(5) . . ? C5 C3 C4 113.3(5) . . ? O3 C4 O4 121.9(6) . . ? O3 C4 C3 119.9(5) . . ? O4 C4 C3 118.2(6) . . ? C3 C5 S1 103.5(4) . . ? C2 O1 Co1 123.6(4) . 2_564 ? C2 O2 Co1 114.9(4) . . ? C4 O3 Co1 116.0(4) . . ? C4 O4 Co1 134.4(5) . 3_655 ? O6 O6 O6 165.6(17) 4_564 3_655 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.454 _refine_diff_density_min -0.526 _refine_diff_density_rms 0.116