# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Winter, Stephen' 'Roberts, Ryan' 'Mailman, Aaron' 'Cvrkalj, Kristina' 'Assoud, Abdeljalil' 'Oakley, Richard' _publ_contact_author_name 'Oakley, Richard' _publ_contact_author_email oakley@sciborg.uwaterloo.ca _publ_section_title ; Thermal conversion of a pyridine-bridged bisdithiazolyl radical to a zwitterionic bisdithiazolopyridone ; # Attachment '- 4a_sbf6.cif' data_meosb_b_0m _database_code_depnum_ccdc_archive 'CCDC 772270' #TrackingRef '- 4a_sbf6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H6 F6 N3 O S4 Sb' _chemical_formula_weight 512.14 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' F F 0.0171 0.0103 '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' Sb Sb -0.5866 1.5461 '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/n loop_ _symmetry_equiv_pos_as_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 8.4861(4) _cell_length_b 13.7971(7) _cell_length_c 13.1136(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.3000(10) _cell_angle_gamma 90.00 _cell_volume 1528.82(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour Red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 2.416 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6437 _exptl_absorpt_correction_T_max 0.9096 _exptl_absorpt_process_details 'APEX II' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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_reflns_number 14995 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3002 _reflns_number_gt 2524 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. ; _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^)+(0.0178P)^2^+2.3927P] 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 3002 _refine_ls_number_parameters 223 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.521 _refine_ls_restrained_S_all 1.513 _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 Sb1 Sb 0.57132(5) 0.10026(3) 0.31943(3) 0.06467(17) Uani 1 1 d . . . S1 S 1.6637(3) 0.36480(19) 0.02411(19) 0.1151(8) Uani 1 1 d . . . S2 S 1.5282(3) 0.41774(16) 0.13539(19) 0.1108(8) Uani 1 1 d . . . S3 S 0.9385(2) 0.09909(14) 0.10025(15) 0.0831(5) Uani 1 1 d . . . S4 S 0.9897(2) 0.21835(15) 0.19246(15) 0.0865(5) Uani 1 1 d . . . N1 N 1.3228(6) 0.1878(3) 0.0079(3) 0.0610(12) Uani 1 1 d . . . N2 N 1.5530(7) 0.2740(4) -0.0130(4) 0.0852(17) Uani 1 1 d . . . N3 N 1.0922(6) 0.1044(4) 0.0338(4) 0.0663(13) Uani 1 1 d . . . O1 O 1.2170(8) 0.3748(5) 0.2436(5) 0.142(3) Uani 1 1 d . . . C1 C 1.4254(7) 0.2621(5) 0.0344(5) 0.0673(16) Uani 1 1 d . . . C2 C 1.3918(8) 0.3276(4) 0.1140(5) 0.0728(18) Uani 1 1 d . . . C3 C 1.2596(8) 0.3167(5) 0.1678(5) 0.0726(18) Uani 1 1 d . . . C4 C 1.1584(7) 0.2413(4) 0.1375(4) 0.0601(14) Uani 1 1 d . . . C5 C 1.1896(6) 0.1757(4) 0.0578(4) 0.0550(13) Uani 1 1 d . . . C6 C 1.3563(8) 0.1199(5) -0.0748(5) 0.0813(19) Uani 1 1 d . . . H6A H 1.2735 0.0725 -0.0838 0.122 Uiso 1 1 calc R . . H6B H 1.4555 0.0880 -0.0568 0.122 Uiso 1 1 calc R . . H6C H 1.3617 0.1553 -0.1374 0.122 Uiso 1 1 calc R . . C7 C 1.2904(12) 0.3920(8) 0.3267(8) 0.148(4) Uani 1 1 d . . . H7A H 1.2301 0.4355 0.3650 0.222 Uiso 1 1 calc R . . H7B H 1.3902 0.4212 0.3160 0.222 Uiso 1 1 calc R . . H7C H 1.3083 0.3326 0.3642 0.222 Uiso 1 1 calc R . . F1A F 0.586(5) 0.055(3) 0.205(3) 0.316(9) Uani 0.383(16) 1 d PU A 1 F1B F 0.667(3) 0.1072(16) 0.2046(15) 0.316(9) Uani 0.617(16) 1 d PU A 2 F2A F 0.7859(13) 0.1013(6) 0.3703(11) 0.166(5) Uani 0.715(14) 1 d PU A 1 F2B F 0.698(3) 0.0910(19) 0.427(3) 0.166(5) Uani 0.285(14) 1 d PU A 2 F3A F 0.5929(13) -0.0308(5) 0.3174(11) 0.174(6) Uani 0.765(15) 1 d PU A 1 F3B F 0.503(5) -0.0072(19) 0.382(4) 0.174(6) Uani 0.235(15) 1 d PU A 2 F4A F 0.519(4) 0.2141(17) 0.360(3) 0.167(5) Uani 0.253(11) 1 d PU A 1 F4B F 0.5999(12) 0.2315(5) 0.2916(9) 0.167(5) Uani 0.747(11) 1 d PU A 2 F5A F 0.407(4) 0.055(3) 0.381(2) 0.231(6) Uani 0.281(9) 1 d P A 1 F5B F 0.5360(15) 0.1369(11) 0.4465(8) 0.231(6) Uani 0.719(9) 1 d P A 2 F6A F 0.443(3) 0.0862(19) 0.202(3) 0.154(5) Uani 0.267(13) 1 d PU A 1 F6B F 0.3654(11) 0.1082(6) 0.2690(11) 0.154(5) Uani 0.733(13) 1 d PU A 2 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 Sb1 0.0634(3) 0.0680(3) 0.0614(3) -0.0009(2) -0.00071(18) 0.01140(19) S1 0.0969(15) 0.1227(18) 0.1220(18) 0.0249(15) -0.0106(13) -0.0487(14) S2 0.1256(18) 0.0873(14) 0.1125(17) 0.0028(12) -0.0272(14) -0.0464(13) S3 0.0790(11) 0.0907(12) 0.0813(12) -0.0118(10) 0.0174(9) -0.0175(9) S4 0.0771(11) 0.1027(14) 0.0807(12) -0.0246(10) 0.0118(9) 0.0022(10) N1 0.067(3) 0.061(3) 0.054(3) 0.000(2) 0.002(2) -0.009(2) N2 0.080(4) 0.091(4) 0.083(4) 0.014(3) -0.004(3) -0.020(3) N3 0.075(3) 0.064(3) 0.060(3) -0.008(2) 0.007(2) -0.012(3) O1 0.159(6) 0.133(5) 0.122(5) -0.072(4) -0.055(4) 0.059(4) C1 0.067(4) 0.066(4) 0.066(4) 0.016(3) -0.014(3) -0.008(3) C2 0.077(4) 0.058(4) 0.076(4) 0.007(3) -0.030(3) -0.010(3) C3 0.084(4) 0.061(4) 0.067(4) -0.012(3) -0.025(3) 0.012(3) C4 0.065(3) 0.061(3) 0.052(3) -0.001(3) -0.006(3) 0.013(3) C5 0.062(3) 0.055(3) 0.046(3) 0.004(2) -0.004(2) 0.001(3) C6 0.089(5) 0.080(5) 0.078(5) -0.015(4) 0.027(4) -0.012(4) C7 0.133(8) 0.195(12) 0.115(8) -0.061(8) 0.005(7) 0.045(8) F1A 0.36(2) 0.36(2) 0.270(13) -0.065(14) 0.268(16) -0.127(15) F1B 0.36(2) 0.36(2) 0.270(13) -0.065(14) 0.268(16) -0.127(15) F2A 0.072(6) 0.130(5) 0.282(14) -0.041(7) -0.059(7) 0.013(5) F2B 0.072(6) 0.130(5) 0.282(14) -0.041(7) -0.059(7) 0.013(5) F3A 0.144(8) 0.061(4) 0.296(14) -0.009(5) -0.095(9) 0.019(4) F3B 0.144(8) 0.061(4) 0.296(14) -0.009(5) -0.095(9) 0.019(4) F4A 0.169(8) 0.085(4) 0.235(11) 0.063(5) -0.050(7) -0.035(5) F4B 0.169(8) 0.085(4) 0.235(11) 0.063(5) -0.050(7) -0.035(5) F5A 0.242(12) 0.347(16) 0.117(7) -0.089(9) 0.082(7) -0.085(11) F5B 0.242(12) 0.347(16) 0.117(7) -0.089(9) 0.082(7) -0.085(11) F6A 0.066(5) 0.120(5) 0.262(13) 0.045(7) -0.054(6) 0.005(4) F6B 0.066(5) 0.120(5) 0.262(13) 0.045(7) -0.054(6) 0.005(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 Sb1 F1A 1.64(3) . ? Sb1 F2B 1.70(3) . ? Sb1 F4A 1.73(3) . ? Sb1 F1B 1.778(13) . ? Sb1 F5A 1.79(3) . ? Sb1 F5B 1.793(8) . ? Sb1 F6B 1.813(7) . ? Sb1 F3B 1.81(4) . ? Sb1 F6A 1.81(3) . ? Sb1 F3A 1.817(8) . ? Sb1 F4B 1.867(8) . ? Sb1 F2A 1.881(9) . ? S1 N2 1.614(6) . ? S1 S2 2.072(4) . ? S2 C2 1.704(6) . ? S3 N3 1.636(5) . ? S3 S4 2.064(3) . ? S4 C4 1.691(6) . ? N1 C5 1.367(7) . ? N1 C1 1.369(7) . ? N1 C6 1.480(7) . ? N2 C1 1.307(8) . ? N3 C5 1.305(7) . ? O1 C7 1.227(10) . ? O1 C3 1.352(8) . ? C1 C2 1.430(9) . ? C2 C3 1.388(9) . ? C3 C4 1.384(8) . ? C4 C5 1.425(8) . ? F1A F6A 1.28(5) . ? F2B F5B 1.56(3) . ? 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 F1A Sb1 F2B 129(2) . . ? F1A Sb1 F4A 132(2) . . ? F2B Sb1 F4A 88.5(13) . . ? F1A Sb1 F1B 33.5(11) . . ? F2B Sb1 F1B 113.8(16) . . ? F4A Sb1 F1B 111.1(15) . . ? F1A Sb1 F5A 114.4(15) . . ? F2B Sb1 F5A 93.2(19) . . ? F4A Sb1 F5A 86.8(19) . . ? F1B Sb1 F5A 147.1(12) . . ? F1A Sb1 F5B 172.2(12) . . ? F2B Sb1 F5B 52.9(12) . . ? F4A Sb1 F5B 52.4(12) . . ? F1B Sb1 F5B 154.2(8) . . ? F5A Sb1 F5B 58.1(9) . . ? F1A Sb1 F6B 80.9(17) . . ? F2B Sb1 F6B 145.4(15) . . ? F4A Sb1 F6B 78.0(10) . . ? F1B Sb1 F6B 100.8(10) . . ? F5A Sb1 F6B 54.7(14) . . ? F5B Sb1 F6B 94.8(7) . . ? F1A Sb1 F3B 99(2) . . ? F2B Sb1 F3B 76.6(15) . . ? F4A Sb1 F3B 120(2) . . ? F1B Sb1 F3B 128.0(19) . . ? F5A Sb1 F3B 38.4(18) . . ? F5B Sb1 F3B 73.9(17) . . ? F6B Sb1 F3B 82.9(10) . . ? F1A Sb1 F6A 43.3(18) . . ? F2B Sb1 F6A 169.3(12) . . ? F4A Sb1 F6A 102.0(14) . . ? F1B Sb1 F6A 64.6(16) . . ? F5A Sb1 F6A 85.3(16) . . ? F5B Sb1 F6A 132.9(14) . . ? F6B Sb1 F6A 38.1(11) . . ? F3B Sb1 F6A 95.9(14) . . ? F1A Sb1 F3A 65.9(16) . . ? F2B Sb1 F3A 83.1(9) . . ? F4A Sb1 F3A 159.6(15) . . ? F1B Sb1 F3A 89.3(9) . . ? F5A Sb1 F3A 75.2(15) . . ? F5B Sb1 F3A 108.6(7) . . ? F6B Sb1 F3A 98.6(4) . . ? F3B Sb1 F3A 39.7(14) . . ? F6A Sb1 F3A 86.2(9) . . ? F1A Sb1 F4B 99.6(15) . . ? F2B Sb1 F4B 98.7(10) . . ? F4A Sb1 F4B 38.8(12) . . ? F1B Sb1 F4B 72.8(8) . . ? F5A Sb1 F4B 123.1(16) . . ? F5B Sb1 F4B 86.8(6) . . ? F6B Sb1 F4B 90.5(4) . . ? F3B Sb1 F4B 159.0(18) . . ? F6A Sb1 F4B 90.9(8) . . ? F3A Sb1 F4B 161.2(7) . . ? F1A Sb1 F2A 100.1(17) . . ? F2B Sb1 F2A 35.6(13) . . ? F4A Sb1 F2A 98.7(9) . . ? F1B Sb1 F2A 78.3(10) . . ? F5A Sb1 F2A 127.6(15) . . ? F5B Sb1 F2A 84.7(6) . . ? F6B Sb1 F2A 176.0(4) . . ? F3B Sb1 F2A 100.7(10) . . ? F6A Sb1 F2A 142.0(14) . . ? F3A Sb1 F2A 85.3(4) . . ? F4B Sb1 F2A 85.6(4) . . ? N2 S1 S2 98.1(3) . . ? C2 S2 S1 92.3(3) . . ? N3 S3 S4 98.15(19) . . ? C4 S4 S3 92.3(2) . . ? C5 N1 C1 120.3(5) . . ? C5 N1 C6 119.8(5) . . ? C1 N1 C6 119.9(5) . . ? C1 N2 S1 116.0(5) . . ? C5 N3 S3 115.0(4) . . ? C7 O1 C3 128.2(7) . . ? N2 C1 N1 120.6(6) . . ? N2 C1 C2 119.8(6) . . ? N1 C1 C2 119.6(6) . . ? C3 C2 C1 121.8(6) . . ? C3 C2 S2 124.4(5) . . ? C1 C2 S2 113.8(6) . . ? O1 C3 C4 117.1(7) . . ? O1 C3 C2 126.4(7) . . ? C4 C3 C2 116.4(6) . . ? C3 C4 C5 122.4(6) . . ? C3 C4 S4 123.0(5) . . ? C5 C4 S4 114.6(4) . . ? N3 C5 N1 120.6(5) . . ? N3 C5 C4 119.9(5) . . ? N1 C5 C4 119.4(5) . . ? F6A F1A Sb1 76(2) . . ? F5B F2B Sb1 66.5(9) . . ? F2B F5B Sb1 60.6(13) . . ? F1A F6A Sb1 61(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.696 _refine_diff_density_min -0.647 _refine_diff_density_rms 0.102 # Attachment '- 5a.cif' data_omebpme_0ma _database_code_depnum_ccdc_archive 'CCDC 772271' #TrackingRef '- 5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H3 N3 O S4' _chemical_formula_weight 261.35 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n n a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 11.1845(10) _cell_length_b 14.4724(12) _cell_length_c 11.3596(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1838.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.888 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.996 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8949 _exptl_absorpt_correction_T_max 0.9537 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 20292 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 30.46 _reflns_number_total 2802 _reflns_number_gt 2124 _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. ; _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^)+(0.0133P)^2^+1.2977P] 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 SHELXL _refine_ls_extinction_coef 0.0011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2802 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0674 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.130 _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 S1A S 0.90518(5) 0.58308(4) 0.00799(5) 0.03997(15) Uani 1 1 d . . . S2A S 0.74037(5) 0.63533(4) 0.05969(5) 0.03830(15) Uani 1 1 d . . . O1A O 0.62074(18) 0.7500 0.2500 0.0399(5) Uani 1 2 d S . . N1A N 0.9944(2) 0.7500 0.2500 0.0316(5) Uani 1 2 d S . . N2A N 0.98942(16) 0.63945(13) 0.10126(17) 0.0371(4) Uani 1 1 d . . . C1A C 0.93232(18) 0.69533(14) 0.17224(18) 0.0290(4) Uani 1 1 d . . . C2A C 0.80511(18) 0.69978(14) 0.16879(18) 0.0285(4) Uani 1 1 d . . . C3A C 0.7349(3) 0.7500 0.2500 0.0297(6) Uani 1 2 d S . . C4A C 1.1257(3) 0.7500 0.2500 0.0523(10) Uani 1 2 d S . . H4AA H 1.1543 0.7917 0.3093 0.078 Uiso 1 1 calc R . . H4AB H 1.1543 0.7695 0.1743 0.078 Uiso 0.25 1 calc PR . . H4AC H 1.1543 0.6888 0.2664 0.078 Uiso 0.25 1 calc PR . . S1B S 0.50036(6) 0.66355(5) 0.43845(6) 0.04535(17) Uani 1 1 d . . . S2B S 0.43824(5) 0.62033(4) 0.27590(5) 0.03941(15) Uani 1 1 d . . . O1B O 0.2500 0.5000 0.15762(19) 0.0418(6) Uani 1 2 d S . . N1B N 0.2500 0.5000 0.5258(2) 0.0375(6) Uani 1 2 d S . . N2B N 0.40971(19) 0.60355(14) 0.52256(17) 0.0440(5) Uani 1 1 d . . . C1B C 0.3314(2) 0.55247(15) 0.46500(19) 0.0343(5) Uani 1 1 d . . . C2B C 0.33131(19) 0.55178(15) 0.33924(19) 0.0324(4) Uani 1 1 d . . . C3B C 0.2500 0.5000 0.2690(3) 0.0321(6) Uani 1 2 d S . . C4B C 0.2500 0.5000 0.6552(3) 0.0498(9) Uani 1 2 d S . . H4BA H 0.1880 0.4598 0.6833 0.075 Uiso 1 1 calc R . . H4BB H 0.2360 0.5616 0.6833 0.075 Uiso 0.25 1 calc PR . . H4BC H 0.3260 0.4786 0.6833 0.075 Uiso 0.25 1 calc PR . . 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 S1A 0.0391(3) 0.0425(3) 0.0383(3) -0.0089(3) 0.0030(2) -0.0007(3) S2A 0.0328(3) 0.0390(3) 0.0431(3) -0.0057(2) -0.0076(2) -0.0016(2) O1A 0.0201(10) 0.0415(13) 0.0582(15) -0.0024(11) 0.000 0.000 N1A 0.0213(11) 0.0391(14) 0.0345(13) -0.0032(11) 0.000 0.000 N2A 0.0297(9) 0.0438(11) 0.0377(10) -0.0059(8) 0.0043(8) 0.0016(8) C1A 0.0274(10) 0.0301(10) 0.0295(10) 0.0035(8) 0.0006(8) 0.0002(8) C2A 0.0253(9) 0.0272(10) 0.0329(10) 0.0034(8) -0.0013(8) -0.0013(8) C3A 0.0253(14) 0.0268(14) 0.0371(15) 0.0034(12) 0.000 0.000 C4A 0.0209(15) 0.073(3) 0.063(2) -0.026(2) 0.000 0.000 S1B 0.0441(3) 0.0462(4) 0.0457(3) -0.0109(3) -0.0044(3) -0.0111(3) S2B 0.0355(3) 0.0441(3) 0.0385(3) -0.0018(2) -0.0007(2) -0.0110(2) O1B 0.0409(13) 0.0560(15) 0.0283(11) 0.000 0.000 -0.0127(11) N1B 0.0450(16) 0.0393(15) 0.0284(13) 0.000 0.000 -0.0036(12) N2B 0.0484(12) 0.0465(12) 0.0370(11) -0.0083(9) -0.0036(9) -0.0072(10) C1B 0.0377(12) 0.0319(11) 0.0331(11) -0.0030(9) -0.0023(9) 0.0026(9) C2B 0.0316(11) 0.0314(11) 0.0343(11) -0.0001(9) -0.0012(9) -0.0015(9) C3B 0.0302(15) 0.0332(15) 0.0329(15) 0.000 0.000 -0.0019(12) C4B 0.065(3) 0.054(2) 0.0303(17) 0.000 0.000 -0.0123(19) _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 S1A N2A 1.636(2) . ? S1A S2A 2.0772(9) . ? S2A C2A 1.712(2) . ? O1A C3A 1.277(3) . ? N1A C1A 1.374(2) 4_565 ? N1A C1A 1.374(2) . ? N1A C4A 1.468(4) . ? N2A C1A 1.309(3) . ? C1A C2A 1.425(3) . ? C2A C3A 1.413(3) . ? C3A C2A 1.413(3) 4_565 ? S1B N2B 1.642(2) . ? S1B S2B 2.0696(9) . ? S2B C2B 1.712(2) . ? O1B C3B 1.265(3) . ? N1B C1B 1.372(3) . ? N1B C1B 1.372(3) 2_565 ? N1B C4B 1.470(4) . ? N2B C1B 1.319(3) . ? C1B C2B 1.429(3) . ? C2B C3B 1.423(3) . ? C3B C2B 1.423(3) 2_565 ? 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 N2A S1A S2A 98.42(7) . . ? C2A S2A S1A 91.59(7) . . ? C1A N1A C1A 119.3(2) 4_565 . ? C1A N1A C4A 120.35(12) 4_565 . ? C1A N1A C4A 120.36(12) . . ? C1A N2A S1A 115.23(16) . . ? N2A C1A N1A 120.35(19) . . ? N2A C1A C2A 119.89(19) . . ? N1A C1A C2A 119.76(19) . . ? C3A C2A C1A 124.1(2) . . ? C3A C2A S2A 121.20(16) . . ? C1A C2A S2A 114.69(16) . . ? O1A C3A C2A 123.77(13) . 4_565 ? O1A C3A C2A 123.77(13) . . ? C2A C3A C2A 112.5(3) 4_565 . ? N2B S1B S2B 98.75(7) . . ? C2B S2B S1B 91.99(8) . . ? C1B N1B C1B 119.6(3) . 2_565 ? C1B N1B C4B 120.20(13) . . ? C1B N1B C4B 120.20(13) 2_565 . ? C1B N2B S1B 114.69(16) . . ? N2B C1B N1B 120.1(2) . . ? N2B C1B C2B 120.0(2) . . ? N1B C1B C2B 119.9(2) . . ? C3B C2B C1B 124.4(2) . . ? C3B C2B S2B 121.04(17) . . ? C1B C2B S2B 114.55(16) . . ? O1B C3B C2B 124.11(13) . . ? O1B C3B C2B 124.11(13) . 2_565 ? C2B C3B C2B 111.8(3) . 2_565 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.278 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.068