# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Santosh Gharpure' _publ_contact_author_email sjgharpure@iitm.ac.in _publ_section_title ; Stereoselective Synthesis and Applications of Nitrogen Substituted Donor-Acceptor Cyclopropanes (N-DACs) in the Divergent Synthesis of Azacycles ; loop_ _publ_author_name S.Gharpure V.Ulabala S.R.B.Reddy # Attachment '- SJG1.cif' data_new1 _database_code_depnum_ccdc_archive 'CCDC 826028' #TrackingRef '- SJG1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H11 N O5' _chemical_formula_sum 'C10 H11 N O5' _chemical_formula_weight 225.20 _chemical_absolute_configuration rm 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P21212 _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 16.4826(6) _cell_length_b 6.8123(3) _cell_length_c 9.0139(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1012.12(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3515 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.1 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9222 _exptl_absorpt_correction_T_max 0.9712 _exptl_absorpt_process_details 'Bruker(SADABS, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker axs kappa apex2 CCD diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7263 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 28.29 _reflns_number_total 2478 _reflns_number_gt 2206 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0499P)^2^+0.0941P] 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 0.006(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.3(10) _refine_ls_number_reflns 2478 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 C1 C 0.68855(8) 1.0178(2) 0.44961(17) 0.0372(3) Uani 1 1 d . . . C2 C 0.65601(11) 0.8113(3) 0.25838(16) 0.0459(4) Uani 1 1 d . . . H2A H 0.6889 0.6945 0.2451 0.055 Uiso 1 1 calc R . . H2B H 0.6293 0.8418 0.1653 0.055 Uiso 1 1 calc R . . C3 C 0.59360(9) 0.7810(2) 0.38215(15) 0.0354(3) Uani 1 1 d . . . H3 H 0.5388 0.8076 0.3453 0.042 Uiso 1 1 calc R . . C4 C 0.59595(8) 0.5839(2) 0.46333(16) 0.0333(3) Uani 1 1 d . . . C5 C 0.60154(8) 0.6260(2) 0.62581(16) 0.0329(3) Uani 1 1 d . . . H5 H 0.6289 0.5347 0.6933 0.040 Uiso 1 1 calc R . . C6 C 0.53285(8) 0.7622(2) 0.68177(14) 0.0321(3) Uani 1 1 d . . . H6 H 0.4869 0.7871 0.6154 0.039 Uiso 1 1 calc R . . C7 C 0.61402(8) 0.8434(2) 0.63904(16) 0.0329(3) Uani 1 1 d . . . H7 H 0.6501 0.8943 0.7165 0.040 Uiso 1 1 calc R . . C8 C 0.51653(9) 0.7497(2) 0.84348(14) 0.0365(3) Uani 1 1 d . . . C9 C 0.41251(11) 0.7326(3) 1.02525(16) 0.0497(4) Uani 1 1 d . . . H9A H 0.4277 0.8509 1.0783 0.060 Uiso 1 1 calc R . . H9B H 0.4387 0.6214 1.0724 0.060 Uiso 1 1 calc R . . C10 C 0.32319(13) 0.7075(4) 1.0270(2) 0.0701(6) Uani 1 1 d . . . H10A H 0.3089 0.5906 0.9735 0.105 Uiso 1 1 calc R . . H10B H 0.2980 0.8190 0.9810 0.105 Uiso 1 1 calc R . . H10C H 0.3048 0.6965 1.1277 0.105 Uiso 1 1 calc R . . N1 N 0.61717(7) 0.92810(18) 0.49216(13) 0.0334(3) Uani 1 1 d . . . O1 O 0.73006(7) 1.12363(18) 0.52328(14) 0.0488(3) Uani 1 1 d . . . O2 O 0.70515(7) 0.97387(19) 0.30693(11) 0.0465(3) Uani 1 1 d . . . O3 O 0.59286(7) 0.42686(17) 0.40360(13) 0.0455(3) Uani 1 1 d . . . O4 O 0.56772(7) 0.7437(2) 0.93793(11) 0.0568(3) Uani 1 1 d . . . O5 O 0.43710(6) 0.74654(19) 0.87042(11) 0.0445(3) Uani 1 1 d . . . 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 C1 0.0354(7) 0.0317(8) 0.0446(7) 0.0084(6) -0.0040(6) -0.0021(6) C2 0.0541(9) 0.0524(10) 0.0312(6) 0.0049(7) -0.0051(6) -0.0079(8) C3 0.0348(6) 0.0353(8) 0.0360(6) 0.0034(6) -0.0094(5) -0.0034(6) C4 0.0279(6) 0.0323(8) 0.0398(7) -0.0007(6) 0.0011(5) -0.0021(6) C5 0.0340(6) 0.0293(7) 0.0354(6) 0.0042(5) -0.0019(5) 0.0021(6) C6 0.0309(6) 0.0316(7) 0.0339(6) -0.0006(6) -0.0012(5) 0.0003(6) C7 0.0318(6) 0.0321(7) 0.0349(6) 0.0001(6) -0.0032(5) -0.0027(6) C8 0.0423(8) 0.0307(7) 0.0366(6) -0.0028(6) -0.0001(5) -0.0013(7) C9 0.0597(9) 0.0540(10) 0.0353(7) -0.0059(8) 0.0093(7) 0.0028(9) C10 0.0608(11) 0.0915(17) 0.0578(10) -0.0144(11) 0.0199(9) -0.0053(11) N1 0.0334(5) 0.0276(6) 0.0390(6) 0.0031(5) -0.0040(4) -0.0035(5) O1 0.0433(6) 0.0434(7) 0.0596(7) -0.0014(6) -0.0025(5) -0.0142(5) O2 0.0480(6) 0.0490(7) 0.0425(5) 0.0091(5) 0.0018(5) -0.0112(5) O3 0.0486(6) 0.0338(6) 0.0541(6) -0.0093(5) 0.0041(5) -0.0044(5) O4 0.0495(6) 0.0839(10) 0.0370(5) 0.0018(6) -0.0081(5) -0.0032(7) O5 0.0428(5) 0.0558(7) 0.0348(5) -0.0031(5) 0.0047(4) 0.0015(6) _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 C1 O1 1.1954(19) . ? C1 O2 1.3484(19) . ? C1 N1 1.3801(18) . ? C2 O2 1.440(2) . ? C2 C3 1.531(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.4625(19) . ? C3 C4 1.530(2) . ? C3 H3 0.9800 . ? C4 O3 1.1985(18) . ? C4 C5 1.4954(19) . ? C5 C7 1.500(2) . ? C5 C6 1.5482(19) . ? C5 H5 0.9800 . ? C6 C8 1.4847(17) . ? C6 C7 1.4980(19) . ? C6 H6 0.9800 . ? C7 N1 1.4451(18) . ? C7 H7 0.9800 . ? C8 O4 1.1994(17) . ? C8 O5 1.3317(18) . ? C9 O5 1.4563(17) . ? C9 C10 1.482(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 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 O1 C1 O2 123.20(14) . . ? O1 C1 N1 126.91(15) . . ? O2 C1 N1 109.87(13) . . ? O2 C2 C3 105.08(12) . . ? O2 C2 H2A 110.7 . . ? C3 C2 H2A 110.7 . . ? O2 C2 H2B 110.7 . . ? C3 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? N1 C3 C4 105.69(11) . . ? N1 C3 C2 102.88(11) . . ? C4 C3 C2 116.75(13) . . ? N1 C3 H3 110.4 . . ? C4 C3 H3 110.4 . . ? C2 C3 H3 110.4 . . ? O3 C4 C5 127.88(14) . . ? O3 C4 C3 124.57(13) . . ? C5 C4 C3 107.54(12) . . ? C4 C5 C7 106.03(12) . . ? C4 C5 C6 112.91(11) . . ? C7 C5 C6 58.85(9) . . ? C4 C5 H5 121.0 . . ? C7 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C8 C6 C7 115.82(11) . . ? C8 C6 C5 114.69(12) . . ? C7 C6 C5 58.95(9) . . ? C8 C6 H6 118.0 . . ? C7 C6 H6 118.0 . . ? C5 C6 H6 118.0 . . ? N1 C7 C6 114.52(11) . . ? N1 C7 C5 109.04(12) . . ? C6 C7 C5 62.19(10) . . ? N1 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C5 C7 H7 119.3 . . ? O4 C8 O5 124.17(13) . . ? O4 C8 C6 124.85(13) . . ? O5 C8 C6 110.98(11) . . ? O5 C9 C10 107.12(14) . . ? O5 C9 H9A 110.3 . . ? C10 C9 H9A 110.3 . . ? O5 C9 H9B 110.3 . . ? C10 C9 H9B 110.3 . . ? H9A C9 H9B 108.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C1 N1 C7 117.52(11) . . ? C1 N1 C3 109.96(12) . . ? C7 N1 C3 109.76(11) . . ? C1 O2 C2 110.26(12) . . ? C8 O5 C9 116.70(12) . . ? 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 O2 C2 C3 N1 -2.29(15) . . . . ? O2 C2 C3 C4 -117.50(13) . . . . ? N1 C3 C4 O3 -167.52(14) . . . . ? C2 C3 C4 O3 -53.88(19) . . . . ? N1 C3 C4 C5 13.20(14) . . . . ? C2 C3 C4 C5 126.84(13) . . . . ? O3 C4 C5 C7 173.15(14) . . . . ? C3 C4 C5 C7 -7.60(15) . . . . ? O3 C4 C5 C6 -124.42(16) . . . . ? C3 C4 C5 C6 54.82(15) . . . . ? C4 C5 C6 C8 158.14(13) . . . . ? C7 C5 C6 C8 -106.42(14) . . . . ? C4 C5 C6 C7 -95.44(13) . . . . ? C8 C6 C7 N1 -156.01(13) . . . . ? C5 C6 C7 N1 99.49(14) . . . . ? C8 C6 C7 C5 104.50(15) . . . . ? C4 C5 C7 N1 -0.89(15) . . . . ? C6 C5 C7 N1 -108.32(12) . . . . ? C4 C5 C7 C6 107.43(12) . . . . ? C7 C6 C8 O4 -22.6(2) . . . . ? C5 C6 C8 O4 43.4(2) . . . . ? C7 C6 C8 O5 157.21(13) . . . . ? C5 C6 C8 O5 -136.88(13) . . . . ? O1 C1 N1 C7 -42.2(2) . . . . ? O2 C1 N1 C7 139.63(13) . . . . ? O1 C1 N1 C3 -168.74(15) . . . . ? O2 C1 N1 C3 13.14(17) . . . . ? C6 C7 N1 C1 175.60(13) . . . . ? C5 C7 N1 C1 -117.04(14) . . . . ? C6 C7 N1 C3 -57.81(16) . . . . ? C5 C7 N1 C3 9.55(15) . . . . ? C4 C3 N1 C1 116.77(12) . . . . ? C2 C3 N1 C1 -6.17(15) . . . . ? C4 C3 N1 C7 -13.98(14) . . . . ? C2 C3 N1 C7 -136.92(12) . . . . ? O1 C1 O2 C2 167.02(15) . . . . ? N1 C1 O2 C2 -14.77(17) . . . . ? C3 C2 O2 C1 10.30(17) . . . . ? O4 C8 O5 C9 -0.8(3) . . . . ? C6 C8 O5 C9 179.48(14) . . . . ? C10 C9 O5 C8 -173.34(17) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.210 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.032 # Attachment '- SJG2.cif' data_new2 _database_code_depnum_ccdc_archive 'CCDC 826029' #TrackingRef '- SJG2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H29 N O8 S2 ' _chemical_formula_sum 'C29 H29 N O8 S2' _chemical_formula_weight 583.65 _chemical_absolute_configuration . 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 Triclinic _symmetry_space_group_name_H-M P1 _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.9762(6) _cell_length_b 8.4759(5) _cell_length_c 11.3641(9) _cell_angle_alpha 83.948(3) _cell_angle_beta 80.632(3) _cell_angle_gamma 73.019(2) _cell_volume 723.61(9) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2727 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 21.15 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 306 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9288 _exptl_absorpt_correction_T_max 0.9568 _exptl_absorpt_process_details 'SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7682 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.23 _reflns_number_total 3873 _reflns_number_gt 3306 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII (Bruker, 2004)' _computing_cell_refinement 'APEXII/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) ' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0701P)^2^+0.1238P] 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 0.07(9) _refine_ls_number_reflns 3873 _refine_ls_number_parameters 364 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.100 _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 C1 C 0.9202(7) -0.3524(6) 0.4882(4) 0.0584(13) Uani 1 1 d . . . C2 C 0.8573(8) -0.4560(6) 0.5711(4) 0.0640(14) Uani 1 1 d . . . H2 H 0.7905 -0.5194 0.5501 0.077 Uiso 1 1 calc R . . C3 C 0.8934(7) -0.4667(6) 0.6874(4) 0.0568(12) Uani 1 1 d . . . H3 H 0.8482 -0.5357 0.7449 0.068 Uiso 1 1 calc R . . C4 C 0.9966(5) -0.3754(5) 0.7189(4) 0.0457(10) Uani 1 1 d . . . C5 C 1.0601(7) -0.2733(6) 0.6302(4) 0.0576(12) Uani 1 1 d . . . H5 H 1.1301 -0.2116 0.6491 0.069 Uiso 1 1 calc R . . C6 C 1.0225(7) -0.2609(6) 0.5152(4) 0.0633(13) Uani 1 1 d . . . H6 H 1.0659 -0.1916 0.4570 0.076 Uiso 1 1 calc R . . C7 C 1.0416(6) -0.3897(5) 0.8425(4) 0.0505(11) Uani 1 1 d . . . H7A H 1.1633 -0.3874 0.8380 0.061 Uiso 1 1 calc R . . H7B H 1.0334 -0.4960 0.8800 0.061 Uiso 1 1 calc R . . C8 C 0.9217(5) -0.2523(5) 0.9225(3) 0.0404(9) Uani 1 1 d . . . H8 H 0.9636 -0.2644 1.0002 0.048 Uiso 1 1 calc R . . C9 C 0.7292(6) -0.2559(6) 0.9396(3) 0.0455(10) Uani 1 1 d . . . C10 C 0.6136(5) -0.0864(6) 0.9110(4) 0.0479(11) Uani 1 1 d . . . H10 H 0.5078 -0.0733 0.8734 0.057 Uiso 1 1 calc R . . C11 C 0.7328(5) 0.0151(5) 0.8667(3) 0.0383(9) Uani 1 1 d . . . H11 H 0.7031 0.0966 0.8001 0.046 Uiso 1 1 calc R . . C12 C 0.6222(5) 0.0472(5) 0.9871(4) 0.0422(9) Uani 1 1 d . . . H12 H 0.6816 0.0129 1.0584 0.051 Uiso 1 1 calc R . . C13 C 0.4720(6) 0.2004(6) 0.9896(4) 0.0479(11) Uani 1 1 d . . . C14 C 0.3279(7) 0.4424(6) 1.0920(5) 0.0638(13) Uani 1 1 d . . . H14A H 0.2111 0.4293 1.0922 0.077 Uiso 1 1 calc R . . H14B H 0.3523 0.5157 1.0240 0.077 Uiso 1 1 calc R . . C15 C 0.3374(10) 0.5111(7) 1.2051(6) 0.089(2) Uani 1 1 d . . . H15A H 0.3196 0.4345 1.2712 0.133 Uiso 1 1 calc R . . H15B H 0.2470 0.6141 1.2153 0.133 Uiso 1 1 calc R . . H15C H 0.4515 0.5290 1.2019 0.133 Uiso 1 1 calc R . . C16 C 0.6058(7) -0.0912(6) 0.4130(4) 0.0572(12) Uani 1 1 d . . . C17 C 0.6420(7) 0.0522(6) 0.3636(4) 0.0623(13) Uani 1 1 d . . . H17 H 0.7085 0.0548 0.2886 0.075 Uiso 1 1 calc R . . C18 C 0.5787(7) 0.1905(6) 0.4265(5) 0.0639(13) Uani 1 1 d . . . H18 H 0.6034 0.2877 0.3932 0.077 Uiso 1 1 calc R . . C19 C 0.4800(7) 0.1916(7) 0.5372(5) 0.0698(14) Uani 1 1 d . . . C20 C 0.4446(8) 0.0457(8) 0.5855(5) 0.0819(18) Uani 1 1 d . . . H20 H 0.3784 0.0430 0.6607 0.098 Uiso 1 1 calc R . . C21 C 0.5057(7) -0.0936(8) 0.5240(5) 0.0762(16) Uani 1 1 d . . . H21 H 0.4801 -0.1906 0.5568 0.091 Uiso 1 1 calc R . . C22 C 0.4137(11) 0.3487(9) 0.6047(7) 0.124(3) Uani 1 1 d . . . H22A H 0.3322 0.3328 0.6739 0.186 Uiso 1 1 calc R . . H22B H 0.3548 0.4383 0.5536 0.186 Uiso 1 1 calc R . . H22C H 0.5120 0.3741 0.6291 0.186 Uiso 1 1 calc R . . C23 C 1.0584(5) 0.0583(5) 1.0170(4) 0.0451(10) Uani 1 1 d . . . C24 C 0.9439(5) 0.2064(5) 1.0584(4) 0.0518(11) Uani 1 1 d . . . H24 H 0.8670 0.2770 1.0098 0.062 Uiso 1 1 calc R . . C25 C 0.9465(7) 0.2467(6) 1.1725(5) 0.0618(13) Uani 1 1 d . . . H25 H 0.8678 0.3441 1.2005 0.074 Uiso 1 1 calc R . . C26 C 1.0610(7) 0.1484(6) 1.2463(5) 0.0578(12) Uani 1 1 d . . . C27 C 1.1748(7) -0.0007(6) 1.2038(4) 0.0627(13) Uani 1 1 d . . . H27 H 1.2521 -0.0705 1.2524 0.075 Uiso 1 1 calc R . . C28 C 1.1730(6) -0.0443(6) 1.0916(4) 0.0511(11) Uani 1 1 d . . . H28 H 1.2491 -0.1436 1.0647 0.061 Uiso 1 1 calc R . . C29 C 1.0673(9) 0.1930(9) 1.3698(6) 0.097(2) Uani 1 1 d . . . H29A H 1.0097 0.3086 1.3777 0.145 Uiso 1 1 calc R . . H29B H 1.1884 0.1694 1.3828 0.145 Uiso 1 1 calc R . . H29C H 1.0079 0.1295 1.4278 0.145 Uiso 1 1 calc R . . N1 N 0.9134(4) -0.0832(4) 0.8657(3) 0.0421(8) Uani 1 1 d . . . O1 O 0.7213(8) -0.2332(5) 0.2100(3) 0.1120(18) Uani 1 1 d . . . O2 O 0.6004(8) -0.3872(6) 0.3828(4) 0.1180(19) Uani 1 1 d . . . O3 O 0.8924(6) -0.3373(5) 0.3658(3) 0.0813(12) Uani 1 1 d . . . O4 O 0.6835(5) -0.3791(4) 0.9651(3) 0.0661(9) Uani 1 1 d . . . O5 O 0.3779(4) 0.2460(5) 0.9145(3) 0.0732(10) Uani 1 1 d . . . O6 O 0.4622(4) 0.2813(4) 1.0855(3) 0.0566(8) Uani 1 1 d . . . O7 O 1.0209(4) 0.1552(4) 0.7973(3) 0.0659(9) Uani 1 1 d . . . O8 O 1.2308(4) -0.1137(4) 0.8411(3) 0.0566(8) Uani 1 1 d . . . S1 S 0.6952(2) -0.27223(17) 0.33563(12) 0.0830(5) Uani 1 1 d . . . S2 S 1.06710(12) 0.00635(12) 0.87054(9) 0.0454(3) Uani 1 1 d . . . 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 C1 0.090(4) 0.041(3) 0.033(2) -0.005(2) -0.006(2) -0.002(3) C2 0.102(4) 0.041(3) 0.053(3) -0.006(2) -0.018(3) -0.021(3) C3 0.088(4) 0.038(3) 0.041(2) 0.0022(19) -0.012(2) -0.012(2) C4 0.054(3) 0.032(2) 0.040(2) -0.0017(18) -0.0016(19) 0.0031(19) C5 0.068(3) 0.054(3) 0.047(3) 0.000(2) -0.001(2) -0.015(2) C6 0.088(4) 0.055(3) 0.040(3) 0.002(2) 0.007(2) -0.021(3) C7 0.055(2) 0.040(3) 0.052(3) 0.0065(19) -0.014(2) -0.005(2) C8 0.049(2) 0.039(2) 0.033(2) 0.0070(17) -0.0114(17) -0.0121(18) C9 0.052(3) 0.057(3) 0.032(2) -0.0072(19) -0.0025(18) -0.024(2) C10 0.037(2) 0.066(3) 0.047(2) -0.008(2) -0.0101(18) -0.020(2) C11 0.035(2) 0.044(2) 0.032(2) 0.0065(17) -0.0099(17) -0.0062(17) C12 0.039(2) 0.045(2) 0.042(2) 0.0032(18) -0.0106(17) -0.0094(18) C13 0.035(2) 0.057(3) 0.051(3) -0.002(2) -0.008(2) -0.0124(19) C14 0.054(3) 0.047(3) 0.085(4) -0.003(3) -0.012(3) -0.003(2) C15 0.123(5) 0.051(3) 0.078(4) -0.013(3) -0.022(4) 0.006(3) C16 0.068(3) 0.063(3) 0.048(3) 0.013(2) -0.023(2) -0.027(3) C17 0.082(3) 0.063(4) 0.044(3) 0.004(2) -0.006(2) -0.027(3) C18 0.070(3) 0.052(3) 0.064(3) 0.007(2) -0.004(2) -0.016(2) C19 0.061(3) 0.067(3) 0.063(3) 0.008(3) -0.006(2) 0.007(3) C20 0.071(4) 0.091(5) 0.060(3) 0.020(3) 0.013(3) -0.006(3) C21 0.074(3) 0.074(4) 0.075(4) 0.028(3) -0.005(3) -0.026(3) C22 0.137(7) 0.082(5) 0.095(5) -0.008(4) 0.024(4) 0.040(4) C23 0.044(2) 0.039(3) 0.055(3) 0.001(2) -0.004(2) -0.021(2) C24 0.039(2) 0.045(3) 0.074(3) 0.003(2) -0.013(2) -0.017(2) C25 0.061(3) 0.048(3) 0.078(4) -0.017(3) -0.004(3) -0.016(2) C26 0.063(3) 0.053(3) 0.065(3) -0.009(2) -0.008(2) -0.026(2) C27 0.066(3) 0.062(3) 0.065(3) 0.005(3) -0.021(3) -0.022(3) C28 0.047(2) 0.047(3) 0.058(3) -0.001(2) -0.008(2) -0.010(2) C29 0.106(5) 0.104(5) 0.095(5) -0.042(4) -0.019(4) -0.036(4) N1 0.0417(18) 0.044(2) 0.0378(18) 0.0065(14) -0.0066(14) -0.0103(15) O1 0.218(6) 0.078(3) 0.044(2) 0.0029(18) -0.049(3) -0.033(3) O2 0.213(6) 0.089(3) 0.098(3) 0.022(2) -0.077(3) -0.092(4) O3 0.132(3) 0.067(2) 0.0318(16) -0.0141(15) -0.0148(19) -0.003(2) O4 0.074(2) 0.065(2) 0.070(2) -0.0088(18) -0.0021(17) -0.039(2) O5 0.056(2) 0.083(3) 0.074(2) -0.0084(19) -0.0309(18) 0.0042(18) O6 0.0540(18) 0.0497(19) 0.062(2) -0.0076(15) -0.0136(15) -0.0044(14) O7 0.067(2) 0.067(2) 0.065(2) 0.0178(17) -0.0074(17) -0.0294(18) O8 0.0355(15) 0.071(2) 0.062(2) -0.0099(16) 0.0014(14) -0.0143(15) S1 0.1522(15) 0.0640(9) 0.0482(7) 0.0050(6) -0.0414(8) -0.0424(10) S2 0.0368(5) 0.0497(7) 0.0481(6) 0.0053(5) -0.0029(4) -0.0144(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.356(7) . ? C1 C6 1.365(7) . ? C1 O3 1.431(5) . ? C2 C3 1.386(6) . ? C2 H2 0.9300 . ? C3 C4 1.390(6) . ? C3 H3 0.9300 . ? C4 C5 1.388(6) . ? C4 C7 1.489(6) . ? C5 C6 1.375(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.545(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.496(5) . ? C8 C9 1.525(6) . ? C8 H8 0.9800 . ? C9 O4 1.196(5) . ? C9 C10 1.498(6) . ? C10 C11 1.459(6) . ? C10 C12 1.518(6) . ? C10 H10 0.9800 . ? C11 N1 1.437(5) . ? C11 C12 1.506(5) . ? C11 H11 0.9800 . ? C12 C13 1.487(6) . ? C12 H12 0.9800 . ? C13 O5 1.188(5) . ? C13 O6 1.328(5) . ? C14 O6 1.469(5) . ? C14 C15 1.487(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.372(7) . ? C16 C21 1.381(7) . ? C16 S1 1.754(5) . ? C17 C18 1.362(7) . ? C17 H17 0.9300 . ? C18 C19 1.370(7) . ? C18 H18 0.9300 . ? C19 C20 1.386(8) . ? C19 C22 1.521(9) . ? C20 C21 1.358(8) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C28 1.394(6) . ? C23 C24 1.396(6) . ? C23 S2 1.751(4) . ? C24 C25 1.379(6) . ? C24 H24 0.9300 . ? C25 C26 1.374(8) . ? C25 H25 0.9300 . ? C26 C27 1.403(7) . ? C26 C29 1.504(7) . ? C27 C28 1.368(7) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? N1 S2 1.630(3) . ? O1 S1 1.427(4) . ? O2 S1 1.413(5) . ? O3 S1 1.589(5) . ? O7 S2 1.424(3) . ? O8 S2 1.416(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 C2 C1 C6 121.8(4) . . ? C2 C1 O3 122.8(5) . . ? C6 C1 O3 115.2(4) . . ? C1 C2 C3 119.4(5) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 120.6(4) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 117.6(4) . . ? C5 C4 C7 121.1(4) . . ? C3 C4 C7 121.3(4) . . ? C6 C5 C4 121.9(5) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C1 C6 C5 118.6(4) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C4 C7 C8 114.2(3) . . ? C4 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C4 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? N1 C8 C9 103.2(3) . . ? N1 C8 C7 112.2(3) . . ? C9 C8 C7 111.4(3) . . ? N1 C8 H8 110.0 . . ? C9 C8 H8 110.0 . . ? C7 C8 H8 110.0 . . ? O4 C9 C10 126.8(4) . . ? O4 C9 C8 123.7(4) . . ? C10 C9 C8 109.3(3) . . ? C11 C10 C9 106.2(3) . . ? C11 C10 C12 60.7(3) . . ? C9 C10 C12 115.1(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C10 H10 120.0 . . ? N1 C11 C10 109.9(3) . . ? N1 C11 C12 117.0(3) . . ? C10 C11 C12 61.6(3) . . ? N1 C11 H11 118.4 . . ? C10 C11 H11 118.4 . . ? C12 C11 H11 118.4 . . ? C13 C12 C11 114.7(3) . . ? C13 C12 C10 116.2(3) . . ? C11 C12 C10 57.7(3) . . ? C13 C12 H12 118.1 . . ? C11 C12 H12 118.1 . . ? C10 C12 H12 118.1 . . ? O5 C13 O6 125.1(4) . . ? O5 C13 C12 124.6(4) . . ? O6 C13 C12 110.3(4) . . ? O6 C14 C15 106.6(4) . . ? O6 C14 H14A 110.4 . . ? C15 C14 H14A 110.4 . . ? O6 C14 H14B 110.4 . . ? C15 C14 H14B 110.4 . . ? H14A C14 H14B 108.6 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 120.2(5) . . ? C17 C16 S1 119.1(4) . . ? C21 C16 S1 120.7(4) . . ? C18 C17 C16 118.8(4) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C17 C18 C19 122.3(5) . . ? C17 C18 H18 118.8 . . ? C19 C18 H18 118.8 . . ? C18 C19 C20 118.1(5) . . ? C18 C19 C22 120.5(6) . . ? C20 C19 C22 121.5(5) . . ? C21 C20 C19 120.6(5) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C16 120.1(5) . . ? C20 C21 H21 120.0 . . ? C16 C21 H21 120.0 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C28 C23 C24 119.1(4) . . ? C28 C23 S2 120.1(3) . . ? C24 C23 S2 120.7(3) . . ? C25 C24 C23 119.0(4) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C26 C25 C24 122.5(4) . . ? C26 C25 H25 118.7 . . ? C24 C25 H25 118.7 . . ? C25 C26 C27 117.9(4) . . ? C25 C26 C29 122.9(5) . . ? C27 C26 C29 119.2(5) . . ? C28 C27 C26 120.7(5) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C27 C28 C23 120.8(4) . . ? C27 C28 H28 119.6 . . ? C23 C28 H28 119.6 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C11 N1 C8 110.7(3) . . ? C11 N1 S2 119.6(3) . . ? C8 N1 S2 122.1(3) . . ? C1 O3 S1 118.5(3) . . ? C13 O6 C14 115.1(4) . . ? O2 S1 O1 120.3(3) . . ? O2 S1 O3 109.9(3) . . ? O1 S1 O3 102.4(3) . . ? O2 S1 C16 108.7(3) . . ? O1 S1 C16 110.5(2) . . ? O3 S1 C16 103.7(2) . . ? O8 S2 O7 120.0(2) . . ? O8 S2 N1 106.27(18) . . ? O7 S2 N1 105.05(18) . . ? O8 S2 C23 107.5(2) . . ? O7 S2 C23 108.3(2) . . ? N1 S2 C23 109.45(17) . . ? 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 C6 C1 C2 C3 1.8(7) . . . . ? O3 C1 C2 C3 178.4(4) . . . . ? C1 C2 C3 C4 -1.5(7) . . . . ? C2 C3 C4 C5 0.5(6) . . . . ? C2 C3 C4 C7 -178.0(4) . . . . ? C3 C4 C5 C6 0.4(7) . . . . ? C7 C4 C5 C6 178.8(4) . . . . ? C2 C1 C6 C5 -0.9(7) . . . . ? O3 C1 C6 C5 -177.8(4) . . . . ? C4 C5 C6 C1 -0.2(7) . . . . ? C5 C4 C7 C8 83.7(5) . . . . ? C3 C4 C7 C8 -97.9(5) . . . . ? C4 C7 C8 N1 -53.2(5) . . . . ? C4 C7 C8 C9 61.9(5) . . . . ? N1 C8 C9 O4 167.6(4) . . . . ? C7 C8 C9 O4 47.1(5) . . . . ? N1 C8 C9 C10 -8.4(4) . . . . ? C7 C8 C9 C10 -128.9(3) . . . . ? O4 C9 C10 C11 -170.8(4) . . . . ? C8 C9 C10 C11 5.1(4) . . . . ? O4 C9 C10 C12 124.4(4) . . . . ? C8 C9 C10 C12 -59.7(4) . . . . ? C9 C10 C11 N1 0.6(4) . . . . ? C12 C10 C11 N1 110.7(3) . . . . ? C9 C10 C11 C12 -110.1(4) . . . . ? N1 C11 C12 C13 154.4(4) . . . . ? C10 C11 C12 C13 -106.5(4) . . . . ? N1 C11 C12 C10 -99.1(4) . . . . ? C11 C10 C12 C13 103.9(4) . . . . ? C9 C10 C12 C13 -160.9(4) . . . . ? C9 C10 C12 C11 95.2(4) . . . . ? C11 C12 C13 O5 41.7(6) . . . . ? C10 C12 C13 O5 -22.9(7) . . . . ? C11 C12 C13 O6 -136.2(4) . . . . ? C10 C12 C13 O6 159.2(4) . . . . ? C21 C16 C17 C18 0.5(8) . . . . ? S1 C16 C17 C18 -177.1(4) . . . . ? C16 C17 C18 C19 -0.1(9) . . . . ? C17 C18 C19 C20 0.0(9) . . . . ? C17 C18 C19 C22 179.4(6) . . . . ? C18 C19 C20 C21 -0.3(9) . . . . ? C22 C19 C20 C21 -179.7(6) . . . . ? C19 C20 C21 C16 0.7(9) . . . . ? C17 C16 C21 C20 -0.8(8) . . . . ? S1 C16 C21 C20 176.7(5) . . . . ? C28 C23 C24 C25 -0.4(6) . . . . ? S2 C23 C24 C25 -177.0(3) . . . . ? C23 C24 C25 C26 1.7(7) . . . . ? C24 C25 C26 C27 -2.1(7) . . . . ? C24 C25 C26 C29 178.7(5) . . . . ? C25 C26 C27 C28 1.2(7) . . . . ? C29 C26 C27 C28 -179.6(5) . . . . ? C26 C27 C28 C23 0.0(7) . . . . ? C24 C23 C28 C27 -0.4(6) . . . . ? S2 C23 C28 C27 176.2(3) . . . . ? C10 C11 N1 C8 -6.2(4) . . . . ? C12 C11 N1 C8 61.2(4) . . . . ? C10 C11 N1 S2 -156.5(3) . . . . ? C12 C11 N1 S2 -89.1(4) . . . . ? C9 C8 N1 C11 8.9(4) . . . . ? C7 C8 N1 C11 128.9(4) . . . . ? C9 C8 N1 S2 158.3(3) . . . . ? C7 C8 N1 S2 -81.7(4) . . . . ? C2 C1 O3 S1 62.5(5) . . . . ? C6 C1 O3 S1 -120.6(5) . . . . ? O5 C13 O6 C14 -3.0(6) . . . . ? C12 C13 O6 C14 174.9(3) . . . . ? C15 C14 O6 C13 179.5(5) . . . . ? C1 O3 S1 O2 -65.4(4) . . . . ? C1 O3 S1 O1 165.6(4) . . . . ? C1 O3 S1 C16 50.6(4) . . . . ? C17 C16 S1 O2 -162.5(4) . . . . ? C21 C16 S1 O2 19.9(5) . . . . ? C17 C16 S1 O1 -28.4(5) . . . . ? C21 C16 S1 O1 154.0(4) . . . . ? C17 C16 S1 O3 80.6(4) . . . . ? C21 C16 S1 O3 -97.0(4) . . . . ? C11 N1 S2 O8 -167.0(3) . . . . ? C8 N1 S2 O8 46.2(3) . . . . ? C11 N1 S2 O7 -38.9(3) . . . . ? C8 N1 S2 O7 174.3(3) . . . . ? C11 N1 S2 C23 77.2(3) . . . . ? C8 N1 S2 C23 -69.6(3) . . . . ? C28 C23 S2 O8 -17.0(4) . . . . ? C24 C23 S2 O8 159.6(3) . . . . ? C28 C23 S2 O7 -147.9(3) . . . . ? C24 C23 S2 O7 28.6(4) . . . . ? C28 C23 S2 N1 98.0(3) . . . . ? C24 C23 S2 N1 -85.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.383 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.059