# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name 'Kilian Muniz' _publ_contact_author_name 'Kilian Muniz' _publ_contact_author_email kmuniz@iciq.es data_mo_pcv839_0m _database_code_depnum_ccdc_archive 'CCDC 866364' #TrackingRef 'web_deposit_cif_file_0_KilianMuniz_1328813586.mo_PCV839_0mX.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 N2 O4 S' _chemical_formula_weight 262.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.5431(11) _cell_length_b 9.8350(12) _cell_length_c 12.1245(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.891(3) _cell_angle_gamma 90.00 _cell_volume 1255.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1285 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.96 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 5723 _diffrn_reflns_av_R_equivalents 0.0607 _diffrn_reflns_av_sigmaI/netI 0.1074 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 29.67 _reflns_number_total 2977 _reflns_number_gt 2019 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution SIR2008 _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0824P)^2^+1.2937P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2977 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1069 _refine_ls_R_factor_gt 0.0724 _refine_ls_wR_factor_ref 0.2067 _refine_ls_wR_factor_gt 0.1810 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 S1 S 0.59265(8) 0.39015(9) 0.19630(6) 0.0238(3) Uani 1 1 d . . . O1 O 0.5739(2) 0.3995(3) 0.31156(19) 0.0321(7) Uani 1 1 d . . . O4 O 0.7937(2) 0.0672(3) 0.19162(19) 0.0277(6) Uani 1 1 d . . . O3 O 0.8173(2) 0.2687(3) 0.28352(19) 0.0280(6) Uani 1 1 d . . . O2 O 0.6617(2) 0.4939(3) 0.1462(2) 0.0313(6) Uani 1 1 d . . . C2 C 0.2763(3) 0.2238(5) 0.0993(3) 0.0325(9) Uani 1 1 d . . . H2A H 0.1972 0.2766 0.0853 0.039 Uiso 1 1 calc R . . H2B H 0.2533 0.1303 0.1211 0.039 Uiso 1 1 calc R . . C6 C 0.7614(3) 0.1813(4) 0.2125(3) 0.0221(7) Uani 1 1 d . . . C7 C 0.9196(3) 0.2261(4) 0.3638(3) 0.0286(9) Uani 1 1 d . . . C3 C 0.3529(3) 0.2203(4) -0.0047(3) 0.0255(8) Uani 1 1 d . . . H3A H 0.3114 0.2764 -0.0640 0.031 Uiso 1 1 calc R . . H3B H 0.3609 0.1260 -0.0320 0.031 Uiso 1 1 calc R . . N1 N 0.4562(3) 0.3666(3) 0.1278(2) 0.0241(7) Uani 1 1 d . . . N2 N 0.6549(3) 0.2407(3) 0.1620(2) 0.0256(7) Uani 1 1 d . . . C5 C 0.5805(3) 0.1720(4) 0.0717(3) 0.0225(7) Uani 1 1 d . . . H5A H 0.5372 0.0904 0.0994 0.027 Uiso 1 1 calc R . . H5B H 0.6358 0.1445 0.0120 0.027 Uiso 1 1 calc R . . C8 C 0.8640(5) 0.1161(5) 0.4365(4) 0.0541(14) Uani 1 1 d . . . H8A H 0.7791 0.1435 0.4572 0.081 Uiso 1 1 calc R . . H8B H 0.9192 0.1040 0.5033 0.081 Uiso 1 1 calc R . . H8C H 0.8583 0.0302 0.3955 0.081 Uiso 1 1 calc R . . C1 C 0.3583(3) 0.2899(4) 0.1897(3) 0.0275(8) Uani 1 1 d . . . H1A H 0.3989 0.2207 0.2391 0.033 Uiso 1 1 calc R . . H1B H 0.3078 0.3524 0.2341 0.033 Uiso 1 1 calc R . . C4 C 0.4838(3) 0.2786(4) 0.0305(3) 0.0233(8) Uani 1 1 d . . . H4 H 0.5183 0.3342 -0.0302 0.028 Uiso 1 1 calc R . . C9 C 0.9453(3) 0.3547(4) 0.4296(3) 0.0328(9) Uani 1 1 d . . . H9A H 0.9718 0.4270 0.3801 0.049 Uiso 1 1 calc R . . H9B H 1.0129 0.3378 0.4864 0.049 Uiso 1 1 calc R . . H9C H 0.8678 0.3826 0.4649 0.049 Uiso 1 1 calc R . . C10 C 1.0351(4) 0.1825(7) 0.3066(4) 0.071(2) Uani 1 1 d . . . H10A H 1.0176 0.0968 0.2675 0.107 Uiso 1 1 calc R . . H10B H 1.1058 0.1695 0.3612 0.107 Uiso 1 1 calc R . . H10C H 1.0577 0.2525 0.2536 0.107 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0324(4) 0.0227(5) 0.0154(4) -0.0022(3) -0.0082(3) 0.0019(3) O1 0.0410(14) 0.0391(17) 0.0152(12) -0.0062(11) -0.0070(10) 0.0049(12) O4 0.0244(11) 0.0304(16) 0.0279(12) -0.0015(11) -0.0032(10) 0.0035(11) O3 0.0320(12) 0.0272(15) 0.0230(12) 0.0000(10) -0.0145(10) 0.0010(11) O2 0.0363(13) 0.0280(16) 0.0289(13) -0.0009(11) -0.0050(11) -0.0027(12) C2 0.0303(17) 0.040(3) 0.0267(18) -0.0072(17) -0.0022(15) -0.0046(17) C6 0.0219(15) 0.026(2) 0.0176(15) 0.0024(14) -0.0027(12) -0.0010(14) C7 0.0195(14) 0.040(2) 0.0251(17) -0.0055(16) -0.0095(13) 0.0054(15) C3 0.0248(15) 0.030(2) 0.0211(16) -0.0051(15) -0.0043(13) -0.0010(15) N1 0.0322(14) 0.0245(17) 0.0148(13) -0.0031(11) -0.0055(11) 0.0027(12) N2 0.0318(14) 0.0240(17) 0.0197(14) -0.0057(12) -0.0124(12) 0.0048(12) C5 0.0274(16) 0.0212(19) 0.0183(15) -0.0040(13) -0.0045(13) 0.0037(14) C8 0.086(4) 0.038(3) 0.035(2) 0.012(2) -0.020(2) -0.004(3) C1 0.0301(17) 0.029(2) 0.0227(16) -0.0014(15) -0.0009(14) -0.0017(15) C4 0.0292(16) 0.025(2) 0.0156(15) -0.0006(14) -0.0043(13) 0.0007(14) C9 0.0301(17) 0.038(2) 0.0291(18) -0.0026(16) -0.0120(15) -0.0038(16) C10 0.0244(19) 0.117(5) 0.072(3) -0.058(4) 0.003(2) 0.002(3) _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 S1 O2 1.409(3) . ? S1 O1 1.424(2) . ? S1 N1 1.641(3) . ? S1 N2 1.671(3) . ? O4 C6 1.203(4) . ? O3 C6 1.332(4) . ? O3 C7 1.476(3) . ? C2 C1 1.508(4) . ? C2 C3 1.532(5) . ? C6 N2 1.381(4) . ? C7 C10 1.495(5) . ? C7 C9 1.512(5) . ? C7 C8 1.531(6) . ? C3 C4 1.535(4) . ? N1 C4 1.503(4) . ? N1 C1 1.509(5) . ? N2 C5 1.478(4) . ? C5 C4 1.529(4) . ? 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 S1 O1 118.45(16) . . ? O2 S1 N1 110.06(15) . . ? O1 S1 N1 110.12(15) . . ? O2 S1 N2 108.18(16) . . ? O1 S1 N2 112.14(15) . . ? N1 S1 N2 95.48(14) . . ? C6 O3 C7 121.8(3) . . ? C1 C2 C3 107.5(3) . . ? O4 C6 O3 128.1(3) . . ? O4 C6 N2 122.2(3) . . ? O3 C6 N2 109.7(3) . . ? O3 C7 C10 111.1(3) . . ? O3 C7 C9 102.5(3) . . ? C10 C7 C9 110.9(3) . . ? O3 C7 C8 107.0(3) . . ? C10 C7 C8 114.1(4) . . ? C9 C7 C8 110.6(3) . . ? C2 C3 C4 105.5(3) . . ? C4 N1 C1 105.4(3) . . ? C4 N1 S1 106.2(2) . . ? C1 N1 S1 115.1(2) . . ? C6 N2 C5 121.6(3) . . ? C6 N2 S1 125.6(2) . . ? C5 N2 S1 112.7(2) . . ? N2 C5 C4 104.4(3) . . ? C2 C1 N1 103.7(3) . . ? N1 C4 C5 106.9(2) . . ? N1 C4 C3 103.1(3) . . ? C5 C4 C3 114.2(3) . . ? _diffrn_measured_fraction_theta_max 0.838 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.997 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.102 # Attachment 'web_deposit_cif_file_1_KilianMuniz_1328813586.mo_PCV705eX.cif' data_mo_pcv705e _database_code_depnum_ccdc_archive 'CCDC 866365' #TrackingRef 'web_deposit_cif_file_1_KilianMuniz_1328813586.mo_PCV705eX.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H32 N2 O6 S' _chemical_formula_weight 416.53 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.1825(6) _cell_length_b 21.4793(14) _cell_length_c 20.4614(12) _cell_angle_alpha 90.00 _cell_angle_beta 103.900(2) _cell_angle_gamma 90.00 _cell_volume 4344.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9914 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.93 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.185 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 57687 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 28.00 _reflns_number_total 10358 _reflns_number_gt 8294 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution SIR2008 _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0583P)^2^+5.9159P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10358 _refine_ls_number_parameters 558 _refine_ls_number_restraints 117 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1554 _refine_ls_wR_factor_gt 0.1464 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.118 _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 1.02154(6) 0.71911(2) 0.69117(3) 0.01541(13) Uani 1 1 d . . . S1B S 0.43089(6) 0.52823(3) 0.80110(3) 0.01701(13) Uani 1 1 d . . . N1 N 1.0954(2) 0.70769(9) 0.77048(9) 0.0171(4) Uani 1 1 d . . . N2 N 0.89870(19) 0.66620(8) 0.68940(9) 0.0155(4) Uani 1 1 d . . . O1 O 1.10714(18) 0.69800(8) 0.65039(8) 0.0229(4) Uani 1 1 d . . . O2 O 0.96636(19) 0.78037(8) 0.68114(10) 0.0283(4) Uani 1 1 d . . . O3 O 0.94842(19) 0.53909(8) 0.67470(8) 0.0224(4) Uani 1 1 d . . . O4 O 0.90191(18) 0.52196(7) 0.77613(8) 0.0191(3) Uani 1 1 d . . . O5 O 0.79343(17) 0.69330(8) 0.58479(8) 0.0208(4) Uani 1 1 d . . . O6 O 0.70298(17) 0.61772(8) 0.63813(8) 0.0202(4) Uani 1 1 d . . . C1 C 1.1007(3) 0.71102(12) 0.88581(12) 0.0243(5) Uani 1 1 d . . . C2 C 1.2470(3) 0.73189(16) 0.91574(14) 0.0368(7) Uani 1 1 d . . . H2A H 1.3036 0.7207 0.8844 0.044 Uiso 1 1 calc R . . H2B H 1.2495 0.7777 0.9210 0.044 Uiso 1 1 calc R . . C3 C 1.3051(3) 0.7017(2) 0.98377(15) 0.0469(9) Uani 1 1 d . . . H3A H 1.3967 0.7186 1.0029 0.056 Uiso 1 1 calc R . . H3B H 1.3139 0.6563 0.9774 0.056 Uiso 1 1 calc R . . C4 C 1.2172(3) 0.7128(2) 1.03328(15) 0.0489(9) Uani 1 1 d . . . H4A H 1.2195 0.7575 1.0451 0.059 Uiso 1 1 calc R . . H4B H 1.2542 0.6890 1.0751 0.059 Uiso 1 1 calc R . . C5 C 1.0711(3) 0.69301(16) 1.00379(14) 0.0367(7) Uani 1 1 d . . . H5A H 1.0670 0.6473 0.9976 0.044 Uiso 1 1 calc R . . H5B H 1.0151 0.7042 1.0354 0.044 Uiso 1 1 calc R . . C6 C 1.0150(3) 0.72469(14) 0.93647(14) 0.0303(6) Uani 1 1 d . . . H6A H 1.0120 0.7702 0.9435 0.036 Uiso 1 1 calc R . . H6B H 0.9212 0.7102 0.9177 0.036 Uiso 1 1 calc R . . C7 C 1.0937(3) 0.64136(12) 0.86352(11) 0.0210(5) Uani 1 1 d . . . H7A H 1.1787 0.6195 0.8850 0.025 Uiso 1 1 calc R . . H7B H 1.0175 0.6200 0.8764 0.025 Uiso 1 1 calc R . . C8 C 1.0443(3) 0.74533(12) 0.82029(13) 0.0249(5) Uani 1 1 d . . . H8A H 0.9441 0.7461 0.8092 0.030 Uiso 1 1 calc R . . H8B H 1.0787 0.7886 0.8224 0.030 Uiso 1 1 calc R . . C9 C 1.0727(2) 0.64175(10) 0.78688(11) 0.0155(4) Uani 1 1 d . . . H9 H 1.1401 0.6140 0.7731 0.019 Uiso 1 1 calc R . . C10 C 0.9264(2) 0.62479(10) 0.74743(11) 0.0127(4) Uani 1 1 d . . . H10 H 0.8605 0.6321 0.7759 0.015 Uiso 1 1 calc R . . C11 C 0.9250(2) 0.55671(10) 0.72637(11) 0.0157(4) Uani 1 1 d . . . C12 C 0.9125(3) 0.45287(10) 0.77361(13) 0.0225(5) Uani 1 1 d . . . C13 C 0.8020(3) 0.42861(12) 0.71647(14) 0.0299(6) Uani 1 1 d . . . H13A H 0.7139 0.4424 0.7225 0.045 Uiso 1 1 calc R . . H13B H 0.8049 0.3830 0.7161 0.045 Uiso 1 1 calc R . . H13C H 0.8153 0.4447 0.6737 0.045 Uiso 1 1 calc R . . C14 C 0.8872(3) 0.43346(13) 0.84090(14) 0.0331(6) Uani 1 1 d . . . H14A H 0.9539 0.4535 0.8774 0.050 Uiso 1 1 calc R . . H14B H 0.8954 0.3881 0.8456 0.050 Uiso 1 1 calc R . . H14C H 0.7959 0.4462 0.8431 0.050 Uiso 1 1 calc R . . C15 C 1.0536(3) 0.43499(13) 0.76801(19) 0.0390(8) Uani 1 1 d . . . H15A H 1.0650 0.4463 0.7233 0.059 Uiso 1 1 calc R . . H15B H 1.0662 0.3900 0.7746 0.059 Uiso 1 1 calc R . . H15C H 1.1209 0.4571 0.8025 0.059 Uiso 1 1 calc R . . C16 C 0.7890(2) 0.65592(10) 0.63591(11) 0.0168(4) Uani 1 1 d . . . C17 C 0.6830(3) 0.68537(14) 0.52414(13) 0.0292(6) Uani 1 1 d . . . H17 H 0.5970 0.6762 0.5377 0.035 Uiso 1 1 calc R . . C18 C 0.7170(4) 0.63187(16) 0.48424(15) 0.0412(8) Uani 1 1 d . . . H18A H 0.8009 0.6410 0.4706 0.062 Uiso 1 1 calc R . . H18B H 0.6433 0.6255 0.4441 0.062 Uiso 1 1 calc R . . H18C H 0.7289 0.5941 0.5119 0.062 Uiso 1 1 calc R . . C19 C 0.6706(3) 0.74668(16) 0.48868(15) 0.0400(8) Uani 1 1 d . . . H19A H 0.6497 0.7792 0.5183 0.060 Uiso 1 1 calc R . . H19B H 0.5978 0.7445 0.4475 0.060 Uiso 1 1 calc R . . H19C H 0.7561 0.7566 0.4770 0.060 Uiso 1 1 calc R . . C1B C 0.3396(2) 0.55638(11) 0.60722(12) 0.0178(5) Uani 1 1 d . . . C2B C 0.1868(3) 0.54423(12) 0.58627(12) 0.0237(5) Uani 1 1 d . . . H2B1 H 0.1710 0.4994 0.5763 0.028 Uiso 1 1 calc R . . H2B2 H 0.1464 0.5547 0.6243 0.028 Uiso 1 1 calc R . . C3B C 0.1161(3) 0.58203(14) 0.52469(13) 0.0299(6) Uani 1 1 d . . . H3B1 H 0.0199 0.5695 0.5108 0.036 Uiso 1 1 calc R . . H3B2 H 0.1195 0.6267 0.5367 0.036 Uiso 1 1 calc R . . C4B C 0.1817(3) 0.57261(14) 0.46600(13) 0.0312(6) Uani 1 1 d . . . H4B1 H 0.1393 0.6010 0.4288 0.037 Uiso 1 1 calc R . . H4B2 H 0.1660 0.5293 0.4493 0.037 Uiso 1 1 calc R . . C5B C 0.3339(3) 0.58518(13) 0.48689(13) 0.0269(6) Uani 1 1 d . . . H5B1 H 0.3745 0.5758 0.4486 0.032 Uiso 1 1 calc R . . H5B2 H 0.3494 0.6298 0.4982 0.032 Uiso 1 1 calc R . . C6B C 0.4030(3) 0.54580(11) 0.54752(12) 0.0213(5) Uani 1 1 d . . . H6B1 H 0.5003 0.5565 0.5609 0.026 Uiso 1 1 calc R . . H6B2 H 0.3953 0.5012 0.5348 0.026 Uiso 1 1 calc R . . C7B C 0.3719(2) 0.62239(10) 0.63811(11) 0.0153(4) Uani 1 1 d . . . H7B1 H 0.4554 0.6390 0.6279 0.018 Uiso 1 1 calc R . . H7B2 H 0.2964 0.6514 0.6198 0.018 Uiso 1 1 calc R . . C9B C 0.3907(2) 0.61455(10) 0.71426(11) 0.0135(4) Uani 1 1 d . . . H9B1 H 0.3250 0.6412 0.7308 0.016 Uiso 1 1 calc R . . C8B C 0.4038(3) 0.51460(11) 0.66740(12) 0.0193(5) Uani 1 1 d . . . H8B1 H 0.3664 0.4719 0.6615 0.023 Uiso 1 1 calc R . . H9B2 H 0.5034 0.5128 0.6747 0.023 Uiso 1 1 calc R . . C10B C 0.5380(2) 0.62630(10) 0.75665(10) 0.0129(4) Uani 1 1 d . . . H10B H 0.6056 0.6172 0.7296 0.015 Uiso 1 1 calc R . . C11B C 0.5462(2) 0.69377(10) 0.77896(11) 0.0147(4) Uani 1 1 d . . . C12B C 0.5667(2) 0.79612(10) 0.72897(12) 0.0176(5) Uani 1 1 d . . . C13B C 0.4215(3) 0.81273(12) 0.72830(14) 0.0275(6) Uani 1 1 d . . . H13D H 0.3598 0.7870 0.6949 0.041 Uiso 1 1 calc R . . H13E H 0.4055 0.8568 0.7166 0.041 Uiso 1 1 calc R . . H13F H 0.4054 0.8051 0.7730 0.041 Uiso 1 1 calc R . . C14B C 0.5985(3) 0.81237(12) 0.66223(14) 0.0278(6) Uani 1 1 d . . . H14D H 0.6918 0.8002 0.6633 0.042 Uiso 1 1 calc R . . H14E H 0.5881 0.8573 0.6545 0.042 Uiso 1 1 calc R . . H14F H 0.5362 0.7901 0.6258 0.042 Uiso 1 1 calc R . . C15B C 0.6672(3) 0.82524(12) 0.78712(14) 0.0289(6) Uani 1 1 d . . . H15D H 0.6480 0.8116 0.8296 0.043 Uiso 1 1 calc R . . H15E H 0.6601 0.8707 0.7838 0.043 Uiso 1 1 calc R . . H15F H 0.7589 0.8124 0.7859 0.043 Uiso 1 1 calc R . . C16B C 0.6609(3) 0.58668(11) 0.86780(12) 0.0202(5) Uani 1 1 d . . . C17B C 0.7555(5) 0.54072(18) 0.97542(18) 0.0370(9) Uani 0.80 1 d PDU A 1 H17C H 0.8392 0.5466 0.9625 0.044 Uiso 0.50 1 d PR A 1 H17B H 0.8414 0.5568 0.9718 0.044 Uiso 0.30 1 d PR A 1 C18B C 0.7576(5) 0.4763(2) 1.0022(2) 0.0491(11) Uani 0.80 1 d PU A 1 H18D H 0.8285 0.4722 1.0439 0.074 Uiso 0.80 1 d PR A 1 H18E H 0.7748 0.4466 0.9687 0.074 Uiso 0.80 1 d PR A 1 H18F H 0.6694 0.4674 1.0113 0.074 Uiso 0.80 1 d PR A 1 C19B C 0.6879(12) 0.5771(6) 1.0238(5) 0.0425(17) Uani 0.30 1 d PDU A 1 H19G H 0.6807 0.6203 1.0113 0.064 Uiso 0.30 1 d PR A 1 H19H H 0.5993 0.5605 1.0215 0.064 Uiso 0.30 1 d PR A 1 H19I H 0.7424 0.5730 1.0689 0.064 Uiso 0.30 1 d PR A 1 C19W C 0.7441(8) 0.5938(3) 1.0221(3) 0.0378(13) Uani 0.50 1 d PDU A 1 H19J H 0.8183 0.6219 1.0240 0.057 Uiso 0.50 1 d PR A 1 H19K H 0.6603 0.6155 1.0055 0.057 Uiso 0.50 1 d PR A 1 H19L H 0.7475 0.5780 1.0663 0.057 Uiso 0.50 1 d PR A 1 O6B O 0.6483(4) 0.54323(14) 0.9134(2) 0.0252(7) Uani 0.80 1 d PU A 1 C17' C 0.7346(16) 0.5640(8) 0.9861(8) 0.0302(15) Uani 0.20 1 d PDU A 2 H17A H 0.7760 0.6044 0.9904 0.036 Uiso 0.20 1 d PR A 2 C18' C 0.8440(17) 0.5137(7) 0.9849(7) 0.039(3) Uani 0.20 1 d PU A 2 H18G H 0.8920 0.5245 0.9515 0.058 Uiso 0.20 1 d PR A 2 H18H H 0.9065 0.5107 1.0282 0.058 Uiso 0.20 1 d PR A 2 H18I H 0.7995 0.4743 0.9737 0.058 Uiso 0.20 1 d PR A 2 C19' C 0.6457(14) 0.5582(7) 1.0369(6) 0.027(2) Uani 0.20 1 d PDU A 2 H19D H 0.5854 0.5931 1.0323 0.040 Uiso 0.20 1 d PR A 2 H19E H 0.5940 0.5205 1.0275 0.040 Uiso 0.20 1 d PR A 2 H19F H 0.7010 0.5568 1.0821 0.040 Uiso 0.20 1 d PR A 2 O6' O 0.633(2) 0.5605(7) 0.9199(10) 0.0290(18) Uani 0.20 1 d PU A 2 N1B N 0.3634(2) 0.54753(8) 0.72330(9) 0.0155(4) Uani 1 1 d . . . N2B N 0.5528(2) 0.58290(9) 0.81296(9) 0.0171(4) Uani 1 1 d . A . O1B O 0.4862(2) 0.46730(8) 0.80387(10) 0.0292(4) Uani 1 1 d . . . O2B O 0.34068(18) 0.54288(9) 0.84226(9) 0.0256(4) Uani 1 1 d . . . O3B O 0.58270(16) 0.72731(7) 0.73144(8) 0.0157(3) Uani 1 1 d . . . O4B O 0.51572(18) 0.71240(8) 0.82852(8) 0.0215(4) Uani 1 1 d . . . O5B O 0.75374(17) 0.62226(8) 0.87067(8) 0.0225(4) Uani 1 1 d . A . 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 0.0167(3) 0.0120(2) 0.0176(3) 0.00089(19) 0.0041(2) -0.0020(2) S1B 0.0185(3) 0.0151(3) 0.0178(3) 0.0035(2) 0.0050(2) -0.0031(2) N1 0.0177(10) 0.0178(9) 0.0149(9) -0.0026(7) 0.0021(8) -0.0031(7) N2 0.0156(10) 0.0149(9) 0.0151(9) 0.0026(7) 0.0019(7) -0.0030(7) O1 0.0195(9) 0.0313(9) 0.0196(8) 0.0037(7) 0.0084(7) -0.0006(7) O2 0.0309(11) 0.0136(8) 0.0376(11) 0.0020(7) 0.0031(8) 0.0010(7) O3 0.0301(10) 0.0197(8) 0.0218(9) -0.0028(7) 0.0148(7) -0.0012(7) O4 0.0282(9) 0.0120(7) 0.0186(8) 0.0020(6) 0.0087(7) -0.0014(6) O5 0.0190(9) 0.0278(9) 0.0143(8) 0.0042(7) 0.0015(7) -0.0003(7) O6 0.0152(8) 0.0280(9) 0.0165(8) -0.0014(7) 0.0019(6) -0.0056(7) C1 0.0214(13) 0.0329(13) 0.0191(12) -0.0087(10) 0.0059(10) -0.0079(10) C2 0.0256(15) 0.060(2) 0.0251(14) -0.0112(13) 0.0062(11) -0.0154(14) C3 0.0206(15) 0.092(3) 0.0248(15) -0.0101(16) -0.0008(12) -0.0144(16) C4 0.0394(19) 0.087(3) 0.0198(14) -0.0146(15) 0.0058(13) -0.0183(18) C5 0.0313(16) 0.060(2) 0.0221(13) -0.0140(13) 0.0130(12) -0.0103(14) C6 0.0267(15) 0.0384(15) 0.0291(14) -0.0151(12) 0.0130(11) -0.0072(11) C7 0.0171(12) 0.0302(13) 0.0144(11) -0.0009(9) 0.0014(9) 0.0027(10) C8 0.0293(14) 0.0206(12) 0.0266(13) -0.0113(10) 0.0101(11) -0.0064(10) C9 0.0122(11) 0.0175(10) 0.0166(10) 0.0014(8) 0.0028(8) 0.0001(8) C10 0.0115(10) 0.0140(10) 0.0128(10) 0.0008(8) 0.0033(8) 0.0000(8) C11 0.0145(11) 0.0149(10) 0.0178(11) 0.0006(8) 0.0041(9) -0.0003(8) C12 0.0271(14) 0.0105(10) 0.0314(13) 0.0052(9) 0.0100(11) 0.0010(9) C13 0.0395(17) 0.0213(12) 0.0320(14) -0.0059(10) 0.0145(12) -0.0088(11) C14 0.0444(18) 0.0225(13) 0.0330(15) 0.0097(11) 0.0108(13) -0.0033(12) C15 0.0279(16) 0.0225(13) 0.070(2) 0.0138(14) 0.0191(15) 0.0060(11) C16 0.0171(12) 0.0191(11) 0.0145(10) 0.0001(8) 0.0045(9) 0.0024(9) C17 0.0183(13) 0.0505(17) 0.0161(12) 0.0059(11) -0.0014(10) -0.0006(12) C18 0.0460(19) 0.0532(19) 0.0222(14) -0.0061(13) 0.0041(13) -0.0106(15) C19 0.0330(17) 0.063(2) 0.0255(14) 0.0170(14) 0.0109(12) 0.0191(15) C1B 0.0184(12) 0.0179(11) 0.0180(11) -0.0046(8) 0.0063(9) -0.0035(9) C2B 0.0184(13) 0.0321(13) 0.0207(12) -0.0085(10) 0.0047(10) -0.0078(10) C3B 0.0181(13) 0.0470(16) 0.0210(13) -0.0067(11) -0.0021(10) -0.0026(11) C4B 0.0275(15) 0.0433(16) 0.0195(12) -0.0073(11) -0.0005(11) -0.0013(12) C5B 0.0266(14) 0.0372(15) 0.0174(12) -0.0034(10) 0.0065(10) 0.0010(11) C6B 0.0207(13) 0.0249(12) 0.0197(12) -0.0065(9) 0.0073(10) -0.0011(9) C7B 0.0152(11) 0.0174(10) 0.0123(10) -0.0002(8) 0.0015(8) -0.0001(8) C9B 0.0135(11) 0.0138(10) 0.0135(10) 0.0005(8) 0.0039(8) -0.0013(8) C8B 0.0223(13) 0.0169(11) 0.0194(11) -0.0052(9) 0.0066(10) -0.0016(9) C10B 0.0140(11) 0.0135(10) 0.0114(10) 0.0009(8) 0.0035(8) -0.0007(8) C11B 0.0134(11) 0.0176(10) 0.0119(10) -0.0013(8) 0.0007(8) -0.0023(8) C12B 0.0203(12) 0.0102(9) 0.0226(12) 0.0004(8) 0.0056(9) 0.0019(8) C13B 0.0242(14) 0.0264(13) 0.0328(14) 0.0058(11) 0.0087(11) 0.0084(10) C14B 0.0367(16) 0.0185(12) 0.0330(14) 0.0070(10) 0.0180(12) 0.0027(10) C15B 0.0288(14) 0.0175(11) 0.0361(15) -0.0056(10) -0.0008(12) -0.0025(10) C16B 0.0199(12) 0.0247(12) 0.0155(11) 0.0028(9) 0.0030(9) 0.0005(9) C17B 0.0441(19) 0.0379(19) 0.0214(15) 0.0102(15) -0.0073(14) -0.0001(16) C18B 0.070(3) 0.046(2) 0.0295(19) 0.0123(17) 0.0072(19) 0.027(2) C19B 0.051(3) 0.038(3) 0.029(3) 0.000(3) -0.010(3) -0.004(3) C19W 0.046(3) 0.034(3) 0.026(2) -0.002(2) -0.006(2) -0.003(2) O6B 0.0289(15) 0.0273(17) 0.0169(13) 0.0112(13) 0.0006(10) -0.0015(13) C17' 0.038(3) 0.030(3) 0.017(2) 0.003(2) -0.003(2) 0.001(3) C18' 0.047(5) 0.034(5) 0.025(4) -0.002(4) -0.013(4) 0.023(4) C19' 0.031(4) 0.032(4) 0.020(4) 0.006(3) 0.013(3) -0.013(3) O6' 0.034(3) 0.030(4) 0.018(3) 0.007(3) -0.004(3) -0.004(3) N1B 0.0178(10) 0.0144(9) 0.0141(9) 0.0002(7) 0.0036(7) -0.0033(7) N2B 0.0181(10) 0.0166(9) 0.0151(9) 0.0056(7) 0.0012(8) -0.0039(7) O1B 0.0349(11) 0.0157(8) 0.0345(10) 0.0043(7) 0.0031(8) 0.0009(7) O2B 0.0216(9) 0.0376(10) 0.0198(9) 0.0059(7) 0.0092(7) -0.0025(8) O3B 0.0213(9) 0.0103(7) 0.0174(8) -0.0006(6) 0.0081(6) -0.0012(6) O4B 0.0273(10) 0.0227(9) 0.0159(8) -0.0038(6) 0.0076(7) 0.0005(7) O5B 0.0179(9) 0.0275(9) 0.0195(8) 0.0005(7) -0.0007(7) -0.0031(7) _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 O1 1.4180(18) . ? S1A O2 1.4262(18) . ? S1A N1 1.635(2) . ? S1A N2 1.6839(19) . ? S1B O1B 1.4208(18) . ? S1B O2B 1.4225(19) . ? S1B N1B 1.6288(19) . ? S1B N2B 1.683(2) . ? N1 C9 1.486(3) . ? N1 C8 1.489(3) . ? N2 C16 1.381(3) . ? N2 C10 1.456(3) . ? O3 C11 1.199(3) . ? O4 C11 1.328(3) . ? O4 C12 1.490(3) . ? O5 C16 1.328(3) . ? O5 C17 1.471(3) . ? O6 C16 1.209(3) . ? C1 C8 1.517(4) . ? C1 C6 1.535(4) . ? C1 C2 1.536(4) . ? C1 C7 1.561(3) . ? C2 C3 1.521(4) . ? C3 C4 1.523(4) . ? C4 C5 1.525(4) . ? C5 C6 1.519(4) . ? C7 C9 1.531(3) . ? C9 C10 1.557(3) . ? C10 C11 1.524(3) . ? C12 C13 1.508(4) . ? C12 C15 1.518(4) . ? C12 C14 1.519(4) . ? C17 C19 1.494(4) . ? C17 C18 1.498(4) . ? C1B C6B 1.529(3) . ? C1B C2B 1.534(3) . ? C1B C8B 1.537(3) . ? C1B C7B 1.555(3) . ? C2B C3B 1.526(4) . ? C3B C4B 1.521(4) . ? C4B C5B 1.529(4) . ? C5B C6B 1.527(4) . ? C7B C9B 1.533(3) . ? C9B N1B 1.486(3) . ? C9B C10B 1.562(3) . ? C8B N1B 1.485(3) . ? C10B N2B 1.461(3) . ? C10B C11B 1.516(3) . ? C11B O4B 1.199(3) . ? C11B O3B 1.332(3) . ? C12B O3B 1.486(2) . ? C12B C15B 1.506(3) . ? C12B C14B 1.518(3) . ? C12B C13B 1.518(3) . ? C16B O5B 1.206(3) . ? C16B O6' 1.30(2) . ? C16B O6B 1.347(5) . ? C16B N2B 1.373(3) . ? C17B O6B 1.463(5) . ? C17B C18B 1.487(5) . ? C17B C19W 1.509(4) . ? C17B C19B 1.546(5) . ? C19B C19W 0.683(13) . ? C17' O6' 1.50(2) . ? C17' C19' 1.539(5) . ? C17' C18' 1.56(2) . ? 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 S1A O2 119.14(11) . . ? O1 S1A N1 109.57(11) . . ? O2 S1A N1 110.64(11) . . ? O1 S1A N2 109.27(10) . . ? O2 S1A N2 110.77(11) . . ? N1 S1A N2 94.72(10) . . ? O1B S1B O2B 119.11(12) . . ? O1B S1B N1B 110.10(11) . . ? O2B S1B N1B 109.95(11) . . ? O1B S1B N2B 111.43(11) . . ? O2B S1B N2B 108.60(11) . . ? N1B S1B N2B 94.99(9) . . ? C9 N1 C8 105.30(18) . . ? C9 N1 S1A 107.92(14) . . ? C8 N1 S1A 116.42(16) . . ? C16 N2 C10 120.66(18) . . ? C16 N2 S1A 125.47(16) . . ? C10 N2 S1A 113.42(14) . . ? C11 O4 C12 120.35(18) . . ? C16 O5 C17 115.51(19) . . ? C8 C1 C6 110.4(2) . . ? C8 C1 C2 109.6(2) . . ? C6 C1 C2 109.2(2) . . ? C8 C1 C7 103.09(18) . . ? C6 C1 C7 112.8(2) . . ? C2 C1 C7 111.6(2) . . ? C3 C2 C1 111.5(2) . . ? C2 C3 C4 112.4(3) . . ? C3 C4 C5 111.5(2) . . ? C6 C5 C4 110.7(3) . . ? C5 C6 C1 112.1(2) . . ? C9 C7 C1 106.23(19) . . ? N1 C8 C1 102.7(2) . . ? N1 C9 C7 104.20(18) . . ? N1 C9 C10 106.69(17) . . ? C7 C9 C10 114.24(19) . . ? N2 C10 C11 111.64(18) . . ? N2 C10 C9 104.68(17) . . ? C11 C10 C9 108.28(18) . . ? O3 C11 O4 127.4(2) . . ? O3 C11 C10 124.2(2) . . ? O4 C11 C10 108.27(18) . . ? O4 C12 C13 108.9(2) . . ? O4 C12 C15 109.4(2) . . ? C13 C12 C15 113.5(2) . . ? O4 C12 C14 102.3(2) . . ? C13 C12 C14 110.5(2) . . ? C15 C12 C14 111.6(2) . . ? O6 C16 O5 127.0(2) . . ? O6 C16 N2 122.3(2) . . ? O5 C16 N2 110.7(2) . . ? O5 C17 C19 105.4(2) . . ? O5 C17 C18 108.6(2) . . ? C19 C17 C18 114.5(2) . . ? C6B C1B C2B 110.23(19) . . ? C6B C1B C8B 111.9(2) . . ? C2B C1B C8B 109.4(2) . . ? C6B C1B C7B 111.83(19) . . ? C2B C1B C7B 111.7(2) . . ? C8B C1B C7B 101.49(17) . . ? C3B C2B C1B 112.7(2) . . ? C4B C3B C2B 111.8(2) . . ? C3B C4B C5B 111.3(2) . . ? C6B C5B C4B 111.6(2) . . ? C5B C6B C1B 111.5(2) . . ? C9B C7B C1B 106.00(17) . . ? N1B C9B C7B 104.57(17) . . ? N1B C9B C10B 105.73(17) . . ? C7B C9B C10B 114.56(18) . . ? N1B C8B C1B 101.30(18) . . ? N2B C10B C11B 112.62(18) . . ? N2B C10B C9B 103.76(17) . . ? C11B C10B C9B 107.33(17) . . ? O4B C11B O3B 127.7(2) . . ? O4B C11B C10B 124.6(2) . . ? O3B C11B C10B 107.59(18) . . ? O3B C12B C15B 109.76(19) . . ? O3B C12B C14B 102.35(18) . . ? C15B C12B C14B 111.3(2) . . ? O3B C12B C13B 109.41(19) . . ? C15B C12B C13B 112.6(2) . . ? C14B C12B C13B 110.8(2) . . ? O5B C16B O6' 124.1(9) . . ? O5B C16B O6B 127.5(3) . . ? O6' C16B O6B 18.9(7) . . ? O5B C16B N2B 122.9(2) . . ? O6' C16B N2B 110.7(9) . . ? O6B C16B N2B 109.5(3) . . ? O6B C17B C18B 107.2(3) . . ? O6B C17B C19W 111.5(4) . . ? C18B C17B C19W 117.9(4) . . ? O6B C17B C19B 100.6(5) . . ? C18B C17B C19B 101.8(6) . . ? C19W C17B C19B 25.8(5) . . ? C19W C19B C17B 74.1(6) . . ? C19B C19W C17B 80.1(6) . . ? C16B O6B C17B 116.8(3) . . ? O6' C17' C19' 102.3(13) . . ? O6' C17' C18' 107.1(13) . . ? C19' C17' C18' 119.6(13) . . ? C16B O6' C17' 118.6(15) . . ? C9B N1B C8B 105.70(17) . . ? C8B N1B S1B 120.11(16) . . ? C9B N1B S1B 108.68(14) . . ? C16B N2B C10B 121.14(19) . . ? C16B N2B S1B 125.30(16) . . ? C10B N2B S1B 113.50(14) . . ? C11B O3B C12B 121.00(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 O1 S1A N1 C9 -82.05(17) . . . . ? O2 S1A N1 C9 144.61(15) . . . . ? N2 S1A N1 C9 30.32(16) . . . . ? O1 S1A N1 C8 159.89(17) . . . . ? O2 S1A N1 C8 26.6(2) . . . . ? N2 S1A N1 C8 -87.73(18) . . . . ? O1 S1A N2 C16 -73.8(2) . . . . ? O2 S1A N2 C16 59.4(2) . . . . ? N1 S1A N2 C16 173.5(2) . . . . ? O1 S1A N2 C10 98.46(17) . . . . ? O2 S1A N2 C10 -128.36(16) . . . . ? N1 S1A N2 C10 -14.18(17) . . . . ? C8 C1 C2 C3 176.5(3) . . . . ? C6 C1 C2 C3 55.4(3) . . . . ? C7 C1 C2 C3 -70.0(3) . . . . ? C1 C2 C3 C4 -54.7(4) . . . . ? C2 C3 C4 C5 53.6(4) . . . . ? C3 C4 C5 C6 -54.2(4) . . . . ? C4 C5 C6 C1 57.1(3) . . . . ? C8 C1 C6 C5 -177.9(2) . . . . ? C2 C1 C6 C5 -57.4(3) . . . . ? C7 C1 C6 C5 67.4(3) . . . . ? C8 C1 C7 C9 15.5(3) . . . . ? C6 C1 C7 C9 134.5(2) . . . . ? C2 C1 C7 C9 -102.1(2) . . . . ? C9 N1 C8 C1 44.2(2) . . . . ? S1A N1 C8 C1 163.68(16) . . . . ? C6 C1 C8 N1 -156.4(2) . . . . ? C2 C1 C8 N1 83.3(2) . . . . ? C7 C1 C8 N1 -35.7(2) . . . . ? C8 N1 C9 C7 -33.8(2) . . . . ? S1A N1 C9 C7 -158.78(15) . . . . ? C8 N1 C9 C10 87.4(2) . . . . ? S1A N1 C9 C10 -37.6(2) . . . . ? C1 C7 C9 N1 10.7(2) . . . . ? C1 C7 C9 C10 -105.4(2) . . . . ? C16 N2 C10 C11 49.8(3) . . . . ? S1A N2 C10 C11 -122.90(17) . . . . ? C16 N2 C10 C9 166.71(19) . . . . ? S1A N2 C10 C9 -6.0(2) . . . . ? N1 C9 C10 N2 26.5(2) . . . . ? C7 C9 C10 N2 141.12(19) . . . . ? N1 C9 C10 C11 145.75(18) . . . . ? C7 C9 C10 C11 -99.7(2) . . . . ? C12 O4 C11 O3 4.2(4) . . . . ? C12 O4 C11 C10 -172.09(19) . . . . ? N2 C10 C11 O3 25.7(3) . . . . ? C9 C10 C11 O3 -89.0(3) . . . . ? N2 C10 C11 O4 -157.86(18) . . . . ? C9 C10 C11 O4 87.4(2) . . . . ? C11 O4 C12 C13 -66.4(3) . . . . ? C11 O4 C12 C15 58.2(3) . . . . ? C11 O4 C12 C14 176.7(2) . . . . ? C17 O5 C16 O6 -1.9(3) . . . . ? C17 O5 C16 N2 178.5(2) . . . . ? C10 N2 C16 O6 9.3(3) . . . . ? S1A N2 C16 O6 -178.94(18) . . . . ? C10 N2 C16 O5 -171.08(19) . . . . ? S1A N2 C16 O5 0.7(3) . . . . ? C16 O5 C17 C19 154.6(2) . . . . ? C16 O5 C17 C18 -82.2(3) . . . . ? C6B C1B C2B C3B -54.1(3) . . . . ? C8B C1B C2B C3B -177.5(2) . . . . ? C7B C1B C2B C3B 70.9(3) . . . . ? C1B C2B C3B C4B 53.6(3) . . . . ? C2B C3B C4B C5B -53.3(3) . . . . ? C3B C4B C5B C6B 55.0(3) . . . . ? C4B C5B C6B C1B -56.4(3) . . . . ? C2B C1B C6B C5B 55.2(3) . . . . ? C8B C1B C6B C5B 177.2(2) . . . . ? C7B C1B C6B C5B -69.7(3) . . . . ? C6B C1B C7B C9B -143.7(2) . . . . ? C2B C1B C7B C9B 92.2(2) . . . . ? C8B C1B C7B C9B -24.2(2) . . . . ? C1B C7B C9B N1B -2.4(2) . . . . ? C1B C7B C9B C10B 112.8(2) . . . . ? C6B C1B C8B N1B 161.23(18) . . . . ? C2B C1B C8B N1B -76.3(2) . . . . ? C7B C1B C8B N1B 41.8(2) . . . . ? N1B C9B C10B N2B -31.9(2) . . . . ? C7B C9B C10B N2B -146.51(18) . . . . ? N1B C9B C10B C11B -151.34(17) . . . . ? C7B C9B C10B C11B 94.1(2) . . . . ? N2B C10B C11B O4B -27.6(3) . . . . ? C9B C10B C11B O4B 86.0(3) . . . . ? N2B C10B C11B O3B 157.00(18) . . . . ? C9B C10B C11B O3B -89.4(2) . . . . ? O6B C17B C19B C19W -118.1(12) . . . . ? C18B C17B C19B C19W 131.7(12) . . . . ? O6B C17B C19W C19B 68.8(14) . . . . ? C18B C17B C19W C19B -55.8(14) . . . . ? O5B C16B O6B C17B 3.7(5) . . . . ? O6' C16B O6B C17B -83(3) . . . . ? N2B C16B O6B C17B -179.9(3) . . . . ? C18B C17B O6B C16B -154.7(3) . . . . ? C19W C17B O6B C16B 74.9(5) . . . . ? C19B C17B O6B C16B 99.3(6) . . . . ? O5B C16B O6' C17' -12.6(17) . . . . ? O6B C16B O6' C17' 94(4) . . . . ? N2B C16B O6' C17' -175.6(11) . . . . ? C19' C17' O6' C16B 154.0(13) . . . . ? C18' C17' O6' C16B -79.4(16) . . . . ? C1B C8B N1B C9B -45.5(2) . . . . ? C1B C8B N1B S1B -168.67(15) . . . . ? C7B C9B N1B C8B 29.8(2) . . . . ? C10B C9B N1B C8B -91.5(2) . . . . ? C7B C9B N1B S1B 159.96(15) . . . . ? C10B C9B N1B S1B 38.7(2) . . . . ? O1B S1B N1B C8B -20.4(2) . . . . ? O2B S1B N1B C8B -153.59(17) . . . . ? N2B S1B N1B C8B 94.55(18) . . . . ? O1B S1B N1B C9B -142.19(15) . . . . ? O2B S1B N1B C9B 84.66(17) . . . . ? N2B S1B N1B C9B -27.20(16) . . . . ? O5B C16B N2B C10B -5.6(4) . . . . ? O6' C16B N2B C10B 157.6(7) . . . . ? O6B C16B N2B C10B 177.8(2) . . . . ? O5B C16B N2B S1B 171.33(19) . . . . ? O6' C16B N2B S1B -25.4(8) . . . . ? O6B C16B N2B S1B -5.3(3) . . . . ? C11B C10B N2B C16B -52.9(3) . . . . ? C9B C10B N2B C16B -168.6(2) . . . . ? C11B C10B N2B S1B 129.86(17) . . . . ? C9B C10B N2B S1B 14.1(2) . . . . ? O1B S1B N2B C16B -56.3(2) . . . . ? O2B S1B N2B C16B 76.8(2) . . . . ? N1B S1B N2B C16B -170.2(2) . . . . ? O1B S1B N2B C10B 120.87(17) . . . . ? O2B S1B N2B C10B -106.01(17) . . . . ? N1B S1B N2B C10B 6.99(17) . . . . ? O4B C11B O3B C12B -10.8(3) . . . . ? C10B C11B O3B C12B 164.45(18) . . . . ? C15B C12B O3B C11B 70.4(3) . . . . ? C14B C12B O3B C11B -171.3(2) . . . . ? C13B C12B O3B C11B -53.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.209 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.077 # Attachment 'web_deposit_cif_file_2_KilianMuniz_1328813586.mo_PCV843_0mX.cif' data_mo_pcv843_0m _database_code_depnum_ccdc_archive 'CCDC 866366' #TrackingRef 'web_deposit_cif_file_2_KilianMuniz_1328813586.mo_PCV843_0mX.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 N2 O4 S' _chemical_formula_weight 324.39 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 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 5.8032(8) _cell_length_b 20.518(3) _cell_length_c 12.8411(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.101(4) _cell_angle_gamma 90.00 _cell_volume 1517.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9874 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 29.45 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9123 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 41843 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 29.89 _reflns_number_total 4176 _reflns_number_gt 3570 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0390P)^2^+0.9222P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4176 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.2833(2) 0.32214(6) 0.55161(10) 0.0145(2) Uani 1 1 d . . . H1A H 0.4233 0.2948 0.5690 0.017 Uiso 1 1 calc R . . H1B H 0.2739 0.3542 0.6085 0.017 Uiso 1 1 calc R . . C2 C 0.2845(2) 0.35609(6) 0.44456(10) 0.0134(2) Uani 1 1 d . . . C3 C 0.1649(2) 0.30617(6) 0.36414(10) 0.0159(3) Uani 1 1 d . . . H3A H 0.0361 0.3271 0.3184 0.019 Uiso 1 1 calc R . . H3B H 0.2779 0.2887 0.3195 0.019 Uiso 1 1 calc R . . C4 C 0.0728(2) 0.25175(6) 0.42832(9) 0.0127(2) Uani 1 1 d . . . H4 H -0.0866 0.2383 0.3973 0.015 Uiso 1 1 calc R . . C5 C 0.2375(2) 0.19166(6) 0.44427(9) 0.0124(2) Uani 1 1 d . . . H5 H 0.4015 0.2060 0.4421 0.015 Uiso 1 1 calc R . . C6 C 0.1747(2) 0.14033(6) 0.36153(9) 0.0126(2) Uani 1 1 d . . . C7 C 0.3178(2) 0.13048(6) 0.28366(10) 0.0155(2) Uani 1 1 d . . . H7 H 0.4549 0.1557 0.2833 0.019 Uiso 1 1 calc R . . C8 C 0.2604(3) 0.08368(7) 0.20629(10) 0.0192(3) Uani 1 1 d . . . H8 H 0.3577 0.0773 0.1529 0.023 Uiso 1 1 calc R . . C9 C 0.0618(3) 0.04639(6) 0.20712(10) 0.0194(3) Uani 1 1 d . . . H9 H 0.0241 0.0140 0.1549 0.023 Uiso 1 1 calc R . . C10 C -0.0828(2) 0.05632(6) 0.28451(11) 0.0186(3) Uani 1 1 d . . . H10 H -0.2191 0.0308 0.2850 0.022 Uiso 1 1 calc R . . C11 C -0.0278(2) 0.10353(6) 0.36089(10) 0.0162(3) Uani 1 1 d . . . H11 H -0.1281 0.1108 0.4128 0.019 Uiso 1 1 calc R . . C12 C 0.5322(2) 0.37145(7) 0.42396(11) 0.0195(3) Uani 1 1 d . . . H12A H 0.5301 0.3888 0.3528 0.029 Uiso 1 1 calc R . . H12B H 0.6256 0.3315 0.4310 0.029 Uiso 1 1 calc R . . H12C H 0.6000 0.4038 0.4749 0.029 Uiso 1 1 calc R . . C13 C 0.1419(2) 0.41904(6) 0.44177(11) 0.0171(3) Uani 1 1 d . . . H13A H 0.2214 0.4507 0.4909 0.026 Uiso 1 1 calc R . . H13B H -0.0120 0.4095 0.4620 0.026 Uiso 1 1 calc R . . H13C H 0.1251 0.4372 0.3706 0.026 Uiso 1 1 calc R . . C14 C 0.3305(2) 0.11847(6) 0.60351(10) 0.0150(2) Uani 1 1 d . . . C15 C 0.6448(3) 0.04758(7) 0.59816(11) 0.0216(3) Uani 1 1 d . . . H15A H 0.7339 0.0690 0.6584 0.032 Uiso 1 1 calc R . . H15B H 0.7512 0.0319 0.5500 0.032 Uiso 1 1 calc R . . H15C H 0.5590 0.0106 0.6226 0.032 Uiso 1 1 calc R . . N1 N 0.06864(19) 0.28145(5) 0.53387(8) 0.0125(2) Uani 1 1 d . . . N2 N 0.2091(2) 0.16909(5) 0.55129(8) 0.0150(2) Uani 1 1 d . . . O1 O 0.16542(17) 0.23679(5) 0.71690(7) 0.0176(2) Uani 1 1 d . . . O2 O -0.18339(17) 0.19838(5) 0.60532(8) 0.0205(2) Uani 1 1 d . . . O3 O 0.29847(19) 0.09978(5) 0.68940(7) 0.0204(2) Uani 1 1 d . . . O4 O 0.48319(17) 0.09359(4) 0.54412(7) 0.0167(2) Uani 1 1 d . . . S1 S 0.05059(6) 0.221222(14) 0.61542(2) 0.01316(8) 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 0.0157(6) 0.0145(5) 0.0129(5) 0.0001(4) 0.0004(4) -0.0024(5) C2 0.0135(6) 0.0132(5) 0.0137(5) 0.0004(4) 0.0023(4) -0.0011(4) C3 0.0229(7) 0.0135(6) 0.0111(5) 0.0012(4) 0.0005(5) -0.0019(5) C4 0.0147(6) 0.0129(5) 0.0102(5) -0.0009(4) 0.0004(4) 0.0009(4) C5 0.0145(6) 0.0127(5) 0.0099(5) 0.0010(4) 0.0010(4) 0.0005(4) C6 0.0152(6) 0.0115(5) 0.0104(5) 0.0011(4) -0.0005(4) 0.0017(4) C7 0.0161(6) 0.0167(6) 0.0137(5) 0.0012(5) 0.0019(5) 0.0018(5) C8 0.0231(7) 0.0214(6) 0.0133(6) -0.0011(5) 0.0031(5) 0.0071(5) C9 0.0252(7) 0.0143(6) 0.0165(6) -0.0032(5) -0.0059(5) 0.0053(5) C10 0.0188(7) 0.0137(6) 0.0219(6) 0.0007(5) -0.0030(5) -0.0014(5) C11 0.0175(6) 0.0157(6) 0.0157(6) 0.0012(5) 0.0033(5) -0.0003(5) C12 0.0137(6) 0.0254(7) 0.0200(6) 0.0014(5) 0.0041(5) 0.0007(5) C13 0.0158(6) 0.0152(6) 0.0203(6) 0.0004(5) 0.0024(5) 0.0006(5) C14 0.0183(6) 0.0113(5) 0.0143(6) -0.0010(4) -0.0021(5) -0.0014(5) C15 0.0220(7) 0.0167(6) 0.0247(7) 0.0048(5) -0.0022(5) 0.0049(5) N1 0.0149(5) 0.0119(5) 0.0107(5) 0.0000(4) 0.0011(4) -0.0008(4) N2 0.0209(6) 0.0140(5) 0.0101(5) 0.0006(4) 0.0023(4) 0.0035(4) O1 0.0239(5) 0.0178(4) 0.0110(4) -0.0011(3) 0.0021(4) 0.0011(4) O2 0.0173(5) 0.0225(5) 0.0223(5) 0.0010(4) 0.0049(4) -0.0051(4) O3 0.0306(6) 0.0165(5) 0.0136(4) 0.0026(3) 0.0011(4) -0.0005(4) O4 0.0183(5) 0.0151(4) 0.0159(4) 0.0016(3) -0.0007(4) 0.0038(4) S1 0.01555(16) 0.01308(14) 0.01112(14) -0.00010(10) 0.00271(11) -0.00068(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.4935(16) . ? C1 C2 1.5419(17) . ? C2 C12 1.5263(18) . ? C2 C13 1.5320(18) . ? C2 C3 1.5558(17) . ? C3 C4 1.5233(17) . ? C4 N1 1.4891(15) . ? C4 C5 1.5577(17) . ? C5 N2 1.4787(15) . ? C5 C6 1.5083(16) . ? C6 C7 1.3913(18) . ? C6 C11 1.3959(18) . ? C7 C8 1.3921(18) . ? C8 C9 1.385(2) . ? C9 C10 1.392(2) . ? C10 C11 1.3873(18) . ? C14 O3 1.2037(16) . ? C14 O4 1.3394(16) . ? C14 N2 1.3814(16) . ? C15 O4 1.4463(15) . ? N1 S1 1.6314(11) . ? N2 S1 1.6898(11) . ? O1 S1 1.4246(10) . ? O2 S1 1.4272(10) . ? 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 N1 C1 C2 102.26(9) . . ? C12 C2 C13 109.85(11) . . ? C12 C2 C1 110.86(11) . . ? C13 C2 C1 109.86(10) . . ? C12 C2 C3 111.93(11) . . ? C13 C2 C3 110.13(10) . . ? C1 C2 C3 104.09(10) . . ? C4 C3 C2 106.32(10) . . ? N1 C4 C3 103.82(10) . . ? N1 C4 C5 106.44(9) . . ? C3 C4 C5 113.63(11) . . ? N2 C5 C6 113.01(10) . . ? N2 C5 C4 103.47(9) . . ? C6 C5 C4 111.66(10) . . ? C7 C6 C11 119.60(12) . . ? C7 C6 C5 119.60(11) . . ? C11 C6 C5 120.79(11) . . ? C6 C7 C8 120.12(13) . . ? C9 C8 C7 120.10(13) . . ? C8 C9 C10 120.00(12) . . ? C11 C10 C9 120.04(13) . . ? C10 C11 C6 120.11(12) . . ? O3 C14 O4 126.03(12) . . ? O3 C14 N2 123.84(13) . . ? O4 C14 N2 110.12(11) . . ? C4 N1 C1 105.09(10) . . ? C4 N1 S1 106.49(8) . . ? C1 N1 S1 116.36(8) . . ? C14 N2 C5 125.29(11) . . ? C14 N2 S1 121.01(9) . . ? C5 N2 S1 112.62(8) . . ? C14 O4 C15 114.27(10) . . ? O1 S1 O2 119.27(6) . . ? O1 S1 N1 110.94(6) . . ? O2 S1 N1 109.04(6) . . ? O1 S1 N2 111.50(6) . . ? O2 S1 N2 108.47(6) . . ? N1 S1 N2 94.86(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 N1 C1 C2 C12 -151.05(10) . . . . ? N1 C1 C2 C13 87.35(12) . . . . ? N1 C1 C2 C3 -30.55(12) . . . . ? C12 C2 C3 C4 127.42(12) . . . . ? C13 C2 C3 C4 -110.08(12) . . . . ? C1 C2 C3 C4 7.64(13) . . . . ? C2 C3 C4 N1 18.34(13) . . . . ? C2 C3 C4 C5 -96.86(12) . . . . ? N1 C4 C5 N2 30.94(12) . . . . ? C3 C4 C5 N2 144.57(10) . . . . ? N1 C4 C5 C6 152.78(10) . . . . ? C3 C4 C5 C6 -93.59(12) . . . . ? N2 C5 C6 C7 -135.88(12) . . . . ? C4 C5 C6 C7 107.96(13) . . . . ? N2 C5 C6 C11 45.46(16) . . . . ? C4 C5 C6 C11 -70.70(14) . . . . ? C11 C6 C7 C8 -0.70(19) . . . . ? C5 C6 C7 C8 -179.38(11) . . . . ? C6 C7 C8 C9 -0.56(19) . . . . ? C7 C8 C9 C10 0.9(2) . . . . ? C8 C9 C10 C11 -0.1(2) . . . . ? C9 C10 C11 C6 -1.2(2) . . . . ? C7 C6 C11 C10 1.58(19) . . . . ? C5 C6 C11 C10 -179.76(12) . . . . ? C3 C4 N1 C1 -38.75(12) . . . . ? C5 C4 N1 C1 81.44(11) . . . . ? C3 C4 N1 S1 -162.77(8) . . . . ? C5 C4 N1 S1 -42.58(11) . . . . ? C2 C1 N1 C4 43.51(12) . . . . ? C2 C1 N1 S1 161.01(8) . . . . ? O3 C14 N2 C5 -177.52(12) . . . . ? O4 C14 N2 C5 1.57(17) . . . . ? O3 C14 N2 S1 15.26(18) . . . . ? O4 C14 N2 S1 -165.65(9) . . . . ? C6 C5 N2 C14 62.72(16) . . . . ? C4 C5 N2 C14 -176.35(11) . . . . ? C6 C5 N2 S1 -129.13(10) . . . . ? C4 C5 N2 S1 -8.20(12) . . . . ? O3 C14 O4 C15 -10.52(18) . . . . ? N2 C14 O4 C15 170.42(11) . . . . ? C4 N1 S1 O1 148.61(8) . . . . ? C1 N1 S1 O1 31.89(11) . . . . ? C4 N1 S1 O2 -78.08(9) . . . . ? C1 N1 S1 O2 165.20(9) . . . . ? C4 N1 S1 N2 33.37(9) . . . . ? C1 N1 S1 N2 -83.35(9) . . . . ? C14 N2 S1 O1 39.28(12) . . . . ? C5 N2 S1 O1 -129.44(9) . . . . ? C14 N2 S1 O2 -94.01(11) . . . . ? C5 N2 S1 O2 97.27(9) . . . . ? C14 N2 S1 N1 154.06(11) . . . . ? C5 N2 S1 N1 -14.66(9) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.450 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.056 # Attachment 'web_deposit_cif_file_3_KilianMuniz_1328813586.PCV842_0mX.cif' data_pcv842_0m _database_code_depnum_ccdc_archive 'CCDC 866367' #TrackingRef 'web_deposit_cif_file_3_KilianMuniz_1328813586.PCV842_0mX.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 N2 O4 S' _chemical_formula_weight 462.55 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 6.5173(6) _cell_length_b 21.874(2) _cell_length_c 15.6036(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.991(3) _cell_angle_gamma 90.00 _cell_volume 2224.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4614 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.42 _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9472 _exptl_absorpt_correction_T_max 0.9982 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 17043 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5087 _reflns_number_gt 3716 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0571P)^2^+0.4014P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5087 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 S1 S 0.44096(7) 0.454058(19) 0.30544(3) 0.01514(11) Uani 1 1 d . . . O1 O 0.65718(18) 0.46420(6) 0.31186(8) 0.0199(3) Uani 1 1 d . . . N1 N 0.3237(2) 0.51644(6) 0.27378(9) 0.0147(3) Uani 1 1 d . . . C1 C 0.1133(3) 0.51510(8) 0.30830(11) 0.0153(4) Uani 1 1 d . . . H1 H 0.0309 0.4827 0.2784 0.018 Uiso 1 1 calc R . . O2 O 0.3738(2) 0.40095(5) 0.25888(8) 0.0207(3) Uani 1 1 d . . . N2 N 0.3275(2) 0.45633(7) 0.40032(9) 0.0176(3) Uani 1 1 d . . . C2 C 0.1486(3) 0.49743(8) 0.40199(11) 0.0173(4) Uani 1 1 d . . . H2A H 0.1780 0.5340 0.4376 0.021 Uiso 1 1 calc R . . H2B H 0.0272 0.4762 0.4249 0.021 Uiso 1 1 calc R . . C3 C 0.0152(3) 0.57668(8) 0.29319(11) 0.0174(4) Uani 1 1 d . . . H3A H 0.0930 0.6086 0.3248 0.021 Uiso 1 1 calc R . . H3B H -0.1272 0.5764 0.3143 0.021 Uiso 1 1 calc R . . O3 O 0.3075(2) 0.42862(6) 0.54000(8) 0.0248(3) Uani 1 1 d . . . C4 C 0.0142(3) 0.59078(8) 0.19727(11) 0.0184(4) Uani 1 1 d . . . H4A H -0.0533 0.6307 0.1871 0.022 Uiso 1 1 calc R . . H4B H -0.0665 0.5591 0.1663 0.022 Uiso 1 1 calc R . . O4 O 0.54588(19) 0.38718(6) 0.45308(7) 0.0197(3) Uani 1 1 d . . . C5 C 0.2344(3) 0.59269(8) 0.16133(11) 0.0153(4) Uani 1 1 d . . . C6 C 0.3374(3) 0.53061(8) 0.18158(10) 0.0160(4) Uani 1 1 d . . . H6A H 0.2690 0.4980 0.1477 0.019 Uiso 1 1 calc R . . H6B H 0.4833 0.5321 0.1651 0.019 Uiso 1 1 calc R . . C7 C 0.2366(3) 0.59830(8) 0.06326(11) 0.0168(4) Uani 1 1 d . . . C8 C 0.4211(3) 0.61259(9) 0.02315(12) 0.0215(4) Uani 1 1 d . . . H8 H 0.5408 0.6197 0.0573 0.026 Uiso 1 1 calc R . . C9 C 0.4329(3) 0.61661(9) -0.06497(12) 0.0252(4) Uani 1 1 d . . . H9 H 0.5601 0.6259 -0.0908 0.030 Uiso 1 1 calc R . . C10 C 0.2584(3) 0.60701(9) -0.11599(12) 0.0243(4) Uani 1 1 d . . . H10 H 0.2652 0.6102 -0.1766 0.029 Uiso 1 1 calc R . . C11 C 0.0763(3) 0.59283(9) -0.07759(12) 0.0242(4) Uani 1 1 d . . . H11 H -0.0430 0.5861 -0.1121 0.029 Uiso 1 1 calc R . . C12 C 0.0640(3) 0.58821(8) 0.01089(12) 0.0209(4) Uani 1 1 d . . . H12 H -0.0633 0.5781 0.0361 0.025 Uiso 1 1 calc R . . C13 C 0.3508(3) 0.64720(8) 0.20117(10) 0.0152(4) Uani 1 1 d . . . C14 C 0.5225(3) 0.64093(8) 0.25492(11) 0.0168(4) Uani 1 1 d . . . H14 H 0.5705 0.6012 0.2693 0.020 Uiso 1 1 calc R . . C15 C 0.6249(3) 0.69179(8) 0.28800(11) 0.0190(4) Uani 1 1 d . . . H15 H 0.7427 0.6864 0.3239 0.023 Uiso 1 1 calc R . . C16 C 0.5562(3) 0.74989(8) 0.26892(11) 0.0210(4) Uani 1 1 d . . . H16 H 0.6253 0.7846 0.2918 0.025 Uiso 1 1 calc R . . C17 C 0.3842(3) 0.75701(8) 0.21567(12) 0.0239(4) Uani 1 1 d . . . H17 H 0.3359 0.7969 0.2020 0.029 Uiso 1 1 calc R . . C18 C 0.2831(3) 0.70641(8) 0.18249(12) 0.0217(4) Uani 1 1 d . . . H18 H 0.1657 0.7120 0.1464 0.026 Uiso 1 1 calc R . . C19 C 0.3884(3) 0.42372(8) 0.47194(11) 0.0176(4) Uani 1 1 d . . . C20 C 0.6192(3) 0.34847(8) 0.52249(11) 0.0194(4) Uani 1 1 d . . . H20A H 0.5171 0.3162 0.5343 0.023 Uiso 1 1 calc R . . H20B H 0.6400 0.3731 0.5752 0.023 Uiso 1 1 calc R . . C21 C 0.8186(3) 0.31998(8) 0.49661(11) 0.0190(4) Uani 1 1 d . . . C22 C 0.8960(3) 0.27169(9) 0.54609(12) 0.0238(4) Uani 1 1 d . . . H22 H 0.8232 0.2581 0.5947 0.029 Uiso 1 1 calc R . . C23 C 1.0785(3) 0.24361(9) 0.52448(13) 0.0274(5) Uani 1 1 d . . . H23 H 1.1314 0.2113 0.5590 0.033 Uiso 1 1 calc R . . C24 C 1.1842(3) 0.26242(9) 0.45284(14) 0.0272(5) Uani 1 1 d . . . H24 H 1.3075 0.2424 0.4374 0.033 Uiso 1 1 calc R . . C25 C 1.1094(3) 0.31042(9) 0.40399(13) 0.0239(4) Uani 1 1 d . . . H25 H 1.1823 0.3237 0.3552 0.029 Uiso 1 1 calc R . . C26 C 0.9276(3) 0.33934(8) 0.42604(11) 0.0192(4) Uani 1 1 d . . . H26 H 0.8778 0.3726 0.3925 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0152(2) 0.0156(2) 0.0148(2) 0.00134(17) 0.00348(16) 0.00067(17) O1 0.0139(6) 0.0245(7) 0.0213(6) 0.0025(5) 0.0030(5) 0.0015(5) N1 0.0128(7) 0.0157(7) 0.0156(7) 0.0019(6) 0.0035(6) 0.0010(6) C1 0.0119(8) 0.0190(9) 0.0151(8) -0.0011(7) 0.0046(7) -0.0013(7) O2 0.0257(7) 0.0162(6) 0.0204(7) -0.0006(5) 0.0055(6) -0.0022(5) N2 0.0166(7) 0.0213(8) 0.0150(7) 0.0012(6) 0.0047(6) 0.0025(6) C2 0.0161(9) 0.0181(9) 0.0178(9) 0.0001(7) 0.0043(7) 0.0008(7) C3 0.0120(8) 0.0223(9) 0.0181(9) 0.0004(7) 0.0029(7) 0.0027(7) O3 0.0278(8) 0.0325(8) 0.0143(6) -0.0009(6) 0.0034(6) 0.0030(6) C4 0.0145(9) 0.0237(9) 0.0170(9) 0.0012(7) 0.0019(7) 0.0014(7) O4 0.0200(7) 0.0245(7) 0.0146(6) 0.0041(5) 0.0013(5) 0.0039(5) C5 0.0124(8) 0.0184(9) 0.0151(8) 0.0006(7) 0.0009(7) 0.0002(7) C6 0.0161(9) 0.0175(9) 0.0145(8) 0.0011(7) 0.0036(7) -0.0008(7) C7 0.0185(9) 0.0158(8) 0.0162(9) -0.0014(7) 0.0017(7) 0.0013(7) C8 0.0182(9) 0.0269(10) 0.0195(9) -0.0004(8) -0.0003(7) -0.0009(8) C9 0.0231(10) 0.0327(11) 0.0199(9) 0.0013(8) 0.0070(8) 0.0001(9) C10 0.0322(11) 0.0274(10) 0.0133(9) -0.0017(8) 0.0016(8) 0.0044(9) C11 0.0253(10) 0.0267(10) 0.0204(10) -0.0037(8) -0.0037(8) -0.0003(8) C12 0.0197(9) 0.0236(9) 0.0194(9) -0.0006(8) 0.0010(7) -0.0020(8) C13 0.0161(9) 0.0170(9) 0.0127(8) -0.0009(7) 0.0040(7) -0.0008(7) C14 0.0149(9) 0.0177(9) 0.0178(9) 0.0019(7) 0.0023(7) 0.0013(7) C15 0.0166(9) 0.0213(9) 0.0192(9) 0.0000(7) 0.0000(7) 0.0006(7) C16 0.0275(10) 0.0184(9) 0.0170(9) -0.0008(7) 0.0000(8) -0.0051(8) C17 0.0338(11) 0.0160(9) 0.0218(10) 0.0006(7) -0.0039(8) 0.0052(8) C18 0.0249(10) 0.0212(9) 0.0189(9) 0.0011(7) -0.0041(8) 0.0038(8) C19 0.0172(9) 0.0183(9) 0.0173(9) -0.0006(7) -0.0003(7) -0.0035(7) C20 0.0201(9) 0.0220(9) 0.0160(9) 0.0039(7) -0.0020(7) -0.0032(8) C21 0.0190(9) 0.0202(9) 0.0177(9) -0.0005(7) -0.0039(7) -0.0029(7) C22 0.0243(10) 0.0248(10) 0.0222(10) 0.0027(8) -0.0040(8) -0.0036(8) C23 0.0276(11) 0.0222(10) 0.0319(11) 0.0004(8) -0.0124(9) 0.0011(8) C24 0.0188(10) 0.0237(10) 0.0389(12) -0.0063(9) -0.0059(9) 0.0003(8) C25 0.0194(10) 0.0230(10) 0.0292(10) -0.0034(8) 0.0011(8) -0.0061(8) C26 0.0210(9) 0.0164(9) 0.0201(9) 0.0003(7) -0.0033(7) -0.0043(7) _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 S1 O1 1.4283(13) . ? S1 O2 1.4346(12) . ? S1 N1 1.6363(14) . ? S1 N2 1.6669(15) . ? N1 C6 1.476(2) . ? N1 C1 1.482(2) . ? C1 C3 1.508(2) . ? C1 C2 1.526(2) . ? N2 C19 1.378(2) . ? N2 C2 1.473(2) . ? C3 C4 1.528(2) . ? O3 C19 1.199(2) . ? C4 C5 1.550(2) . ? O4 C19 1.338(2) . ? O4 C20 1.449(2) . ? C5 C7 1.535(2) . ? C5 C13 1.539(2) . ? C5 C6 1.545(2) . ? C7 C12 1.397(2) . ? C7 C8 1.400(3) . ? C8 C9 1.381(3) . ? C9 C10 1.393(3) . ? C10 C11 1.374(3) . ? C11 C12 1.388(3) . ? C13 C14 1.393(2) . ? C13 C18 1.397(2) . ? C14 C15 1.392(2) . ? C15 C16 1.378(2) . ? C16 C17 1.392(3) . ? C17 C18 1.384(3) . ? C20 C21 1.503(3) . ? C21 C26 1.387(3) . ? C21 C22 1.397(3) . ? C22 C23 1.385(3) . ? C23 C24 1.386(3) . ? C24 C25 1.382(3) . ? C25 C26 1.391(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 O1 S1 O2 116.96(8) . . ? O1 S1 N1 110.30(7) . . ? O2 S1 N1 112.67(7) . . ? O1 S1 N2 112.67(7) . . ? O2 S1 N2 109.74(8) . . ? N1 S1 N2 91.79(7) . . ? C6 N1 C1 115.50(13) . . ? C6 N1 S1 115.70(11) . . ? C1 N1 S1 107.71(11) . . ? N1 C1 C3 108.55(14) . . ? N1 C1 C2 103.19(13) . . ? C3 C1 C2 115.64(14) . . ? C19 N2 C2 121.22(14) . . ? C19 N2 S1 125.37(12) . . ? C2 N2 S1 113.41(11) . . ? N2 C2 C1 104.12(14) . . ? C1 C3 C4 109.16(14) . . ? C3 C4 C5 111.81(14) . . ? C19 O4 C20 115.41(14) . . ? C7 C5 C13 109.12(14) . . ? C7 C5 C6 105.21(13) . . ? C13 C5 C6 112.88(14) . . ? C7 C5 C4 112.80(14) . . ? C13 C5 C4 109.14(14) . . ? C6 C5 C4 107.70(14) . . ? N1 C6 C5 110.52(14) . . ? C12 C7 C8 117.58(16) . . ? C12 C7 C5 123.29(16) . . ? C8 C7 C5 119.10(15) . . ? C9 C8 C7 121.49(17) . . ? C8 C9 C10 120.02(18) . . ? C11 C10 C9 119.18(17) . . ? C10 C11 C12 121.03(17) . . ? C11 C12 C7 120.69(18) . . ? C14 C13 C18 117.64(16) . . ? C14 C13 C5 123.52(15) . . ? C18 C13 C5 118.84(15) . . ? C15 C14 C13 121.30(16) . . ? C16 C15 C14 120.31(16) . . ? C15 C16 C17 119.17(17) . . ? C18 C17 C16 120.45(17) . . ? C17 C18 C13 121.13(17) . . ? O3 C19 O4 126.81(16) . . ? O3 C19 N2 123.19(17) . . ? O4 C19 N2 110.00(15) . . ? O4 C20 C21 108.49(14) . . ? C26 C21 C22 118.98(18) . . ? C26 C21 C20 122.94(16) . . ? C22 C21 C20 118.07(17) . . ? C23 C22 C21 120.26(19) . . ? C22 C23 C24 120.37(18) . . ? C25 C24 C23 119.68(19) . . ? C24 C25 C26 120.19(19) . . ? C21 C26 C25 120.50(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 O1 S1 N1 C6 76.93(13) . . . . ? O2 S1 N1 C6 -55.79(14) . . . . ? N2 S1 N1 C6 -168.07(12) . . . . ? O1 S1 N1 C1 -152.13(10) . . . . ? O2 S1 N1 C1 75.15(12) . . . . ? N2 S1 N1 C1 -37.13(11) . . . . ? C6 N1 C1 C3 -58.71(18) . . . . ? S1 N1 C1 C3 170.24(11) . . . . ? C6 N1 C1 C2 178.10(13) . . . . ? S1 N1 C1 C2 47.05(14) . . . . ? O1 S1 N2 C19 -51.41(17) . . . . ? O2 S1 N2 C19 80.79(16) . . . . ? N1 S1 N2 C19 -164.32(15) . . . . ? O1 S1 N2 C2 128.85(12) . . . . ? O2 S1 N2 C2 -98.95(13) . . . . ? N1 S1 N2 C2 15.95(13) . . . . ? C19 N2 C2 C1 -170.55(15) . . . . ? S1 N2 C2 C1 9.20(17) . . . . ? N1 C1 C2 N2 -33.46(16) . . . . ? C3 C1 C2 N2 -151.82(15) . . . . ? N1 C1 C3 C4 57.87(17) . . . . ? C2 C1 C3 C4 173.22(14) . . . . ? C1 C3 C4 C5 -60.33(19) . . . . ? C3 C4 C5 C7 172.38(14) . . . . ? C3 C4 C5 C13 -66.15(18) . . . . ? C3 C4 C5 C6 56.73(18) . . . . ? C1 N1 C6 C5 56.97(18) . . . . ? S1 N1 C6 C5 -175.90(11) . . . . ? C7 C5 C6 N1 -173.55(13) . . . . ? C13 C5 C6 N1 67.55(18) . . . . ? C4 C5 C6 N1 -52.99(17) . . . . ? C13 C5 C7 C12 -135.75(17) . . . . ? C6 C5 C7 C12 102.87(18) . . . . ? C4 C5 C7 C12 -14.3(2) . . . . ? C13 C5 C7 C8 46.1(2) . . . . ? C6 C5 C7 C8 -75.34(19) . . . . ? C4 C5 C7 C8 167.52(16) . . . . ? C12 C7 C8 C9 0.0(3) . . . . ? C5 C7 C8 C9 178.29(17) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C7 0.4(3) . . . . ? C8 C7 C12 C11 -0.5(3) . . . . ? C5 C7 C12 C11 -178.77(16) . . . . ? C7 C5 C13 C14 -120.98(17) . . . . ? C6 C5 C13 C14 -4.4(2) . . . . ? C4 C5 C13 C14 115.35(18) . . . . ? C7 C5 C13 C18 58.6(2) . . . . ? C6 C5 C13 C18 175.18(16) . . . . ? C4 C5 C13 C18 -65.1(2) . . . . ? C18 C13 C14 C15 -0.9(3) . . . . ? C5 C13 C14 C15 178.71(16) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C14 C15 C16 C17 -0.5(3) . . . . ? C15 C16 C17 C18 0.2(3) . . . . ? C16 C17 C18 C13 -0.2(3) . . . . ? C14 C13 C18 C17 0.5(3) . . . . ? C5 C13 C18 C17 -179.05(17) . . . . ? C20 O4 C19 O3 2.2(3) . . . . ? C20 O4 C19 N2 -177.65(14) . . . . ? C2 N2 C19 O3 -3.5(3) . . . . ? S1 N2 C19 O3 176.81(14) . . . . ? C2 N2 C19 O4 176.34(14) . . . . ? S1 N2 C19 O4 -3.4(2) . . . . ? C19 O4 C20 C21 -169.11(14) . . . . ? O4 C20 C21 C26 12.4(2) . . . . ? O4 C20 C21 C22 -167.34(15) . . . . ? C26 C21 C22 C23 -0.3(3) . . . . ? C20 C21 C22 C23 179.51(17) . . . . ? C21 C22 C23 C24 -1.1(3) . . . . ? C22 C23 C24 C25 1.6(3) . . . . ? C23 C24 C25 C26 -0.7(3) . . . . ? C22 C21 C26 C25 1.1(3) . . . . ? C20 C21 C26 C25 -178.64(16) . . . . ? C24 C25 C26 C21 -0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.451 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.059 # Attachment 'web_deposit_cif_file_4_KilianMuniz_1328813586.PCV840X.cif' data_pcv840 _database_code_depnum_ccdc_archive 'CCDC 866368' #TrackingRef 'web_deposit_cif_file_4_KilianMuniz_1328813586.PCV840X.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H22 N2 O4 S' _chemical_formula_weight 302.39 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 13.355(3) _cell_length_b 10.423(2) _cell_length_c 11.320(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.797(7) _cell_angle_gamma 90.00 _cell_volume 1500.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4110 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 26.00 _exptl_crystal_description plate _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9341 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 19152 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.43 _reflns_number_total 3354 _reflns_number_gt 2380 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0580P)^2^+0.9322P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3354 _refine_ls_number_parameters 239 _refine_ls_number_restraints 86 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.051 _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 S1 S 0.35947(5) 0.08689(5) 0.19832(5) 0.02133(17) Uani 1 1 d . B . N1 N 0.45320(16) 0.08807(17) 0.33028(18) 0.0222(4) Uani 1 1 d . . . N2 N 0.32889(16) 0.24313(18) 0.20214(18) 0.0245(5) Uani 1 1 d . . . O1 O 0.40071(14) 0.06042(16) 0.09843(15) 0.0265(4) Uani 1 1 d . . . O2 O 0.27354(14) 0.01169(16) 0.20910(16) 0.0302(4) Uani 1 1 d . . . O3 O 0.21507(15) 0.40792(16) 0.13649(17) 0.0315(4) Uani 1 1 d . . . O4 O 0.19743(13) 0.22279(16) 0.02543(15) 0.0264(4) Uani 1 1 d . . . C1 C 0.4294(2) 0.1900(2) 0.4104(2) 0.0233(5) Uani 1 1 d . B . H1 H 0.3775 0.1576 0.4511 0.028 Uiso 1 1 calc R A 1 C2 C 0.5358(5) 0.2139(9) 0.5078(7) 0.0226(18) Uani 0.626(5) 1 d PDU B 1 H2A H 0.5346 0.1820 0.5898 0.027 Uiso 0.626(5) 1 calc PR B 1 H2B H 0.5515 0.3069 0.5148 0.027 Uiso 0.626(5) 1 calc PR B 1 C3 C 0.6196(3) 0.1423(4) 0.4666(4) 0.0229(10) Uani 0.626(5) 1 d PD B 1 H3 H 0.6338 0.0583 0.5113 0.027 Uiso 0.626(5) 1 calc PR B 1 C4 C 0.5649(5) 0.1158(6) 0.3285(5) 0.0239(16) Uani 0.626(5) 1 d PDU B 1 H4A H 0.5674 0.1915 0.2766 0.029 Uiso 0.626(5) 1 calc PR B 1 H4B H 0.5961 0.0409 0.2989 0.029 Uiso 0.626(5) 1 calc PR B 1 C5 C 0.7235(3) 0.2132(5) 0.4899(5) 0.0243(15) Uani 0.626(5) 1 d PDU B 1 H5A H 0.7730 0.1588 0.4625 0.029 Uiso 0.626(5) 1 calc PR B 1 H5B H 0.7116 0.2928 0.4400 0.029 Uiso 0.626(5) 1 calc PR B 1 C6 C 0.7718(3) 0.2466(4) 0.6243(4) 0.0284(11) Uani 0.626(5) 1 d PD B 1 H6 H 0.7949 0.1783 0.6818 0.034 Uiso 0.626(5) 1 calc PR B 1 C7 C 0.7842(4) 0.3645(4) 0.6673(5) 0.0328(13) Uani 0.626(5) 1 d PD B 1 H7A H 0.7619 0.4348 0.6122 0.039 Uiso 0.626(5) 1 calc PR B 1 H7B H 0.8154 0.3794 0.7536 0.039 Uiso 0.626(5) 1 calc PR B 1 C2' C 0.5358(8) 0.2300(17) 0.4974(14) 0.024(2) Uani 0.374(5) 1 d PDU B 2 H2'1 H 0.5555 0.1770 0.5736 0.029 Uiso 0.374(5) 1 calc PR B 2 H2'2 H 0.5356 0.3215 0.5207 0.029 Uiso 0.374(5) 1 calc PR B 2 C3' C 0.6110(5) 0.2068(6) 0.4207(6) 0.0219(14) Uani 0.374(5) 1 d PDU B 2 H3' H 0.6082 0.2827 0.3658 0.026 Uiso 0.374(5) 1 calc PR B 2 C4' C 0.5631(8) 0.0910(11) 0.3394(10) 0.022(2) Uani 0.374(5) 1 d PDU B 2 H4'1 H 0.5718 0.1001 0.2560 0.026 Uiso 0.374(5) 1 calc PR B 2 H4'2 H 0.5981 0.0108 0.3775 0.026 Uiso 0.374(5) 1 calc PR B 2 C5' C 0.7249(5) 0.1851(10) 0.4990(9) 0.0245(19) Uani 0.374(5) 1 d PDU B 2 H5'1 H 0.7288 0.1102 0.5540 0.029 Uiso 0.374(5) 1 calc PR B 2 H5'2 H 0.7681 0.1661 0.4439 0.029 Uiso 0.374(5) 1 calc PR B 2 C6' C 0.7679(5) 0.3014(6) 0.5760(6) 0.0270(16) Uani 0.374(5) 1 d PDU B 2 H6' H 0.7777 0.3767 0.5335 0.032 Uiso 0.374(5) 1 calc PR B 2 C7' C 0.7931(7) 0.3073(8) 0.6970(5) 0.0281(18) Uani 0.374(5) 1 d PDU B 2 H7'1 H 0.7845 0.2341 0.7430 0.034 Uiso 0.374(5) 1 calc PR B 2 H7'2 H 0.8199 0.3849 0.7389 0.034 Uiso 0.374(5) 1 calc PR B 2 C8 C 0.3821(2) 0.3019(2) 0.3237(2) 0.0262(6) Uani 1 1 d . B . H8A H 0.3313 0.3500 0.3546 0.031 Uiso 1 1 calc R . . H8B H 0.4380 0.3615 0.3174 0.031 Uiso 1 1 calc R . . C9 C 0.24189(19) 0.3008(2) 0.1205(2) 0.0231(5) Uani 1 1 d . B . C10 C 0.09136(19) 0.2536(2) -0.0622(2) 0.0265(6) Uani 1 1 d . B . C11 C 0.0664(2) 0.1338(3) -0.1416(3) 0.0369(7) Uani 1 1 d . . . H11A H 0.1196 0.1219 -0.1840 0.055 Uiso 1 1 calc R B . H11B H -0.0031 0.1426 -0.2033 0.055 Uiso 1 1 calc R . . H11C H 0.0664 0.0592 -0.0888 0.055 Uiso 1 1 calc R . . C12 C 0.0991(2) 0.3699(3) -0.1383(2) 0.0366(7) Uani 1 1 d . . . H12A H 0.1143 0.4459 -0.0847 0.055 Uiso 1 1 calc R B . H12B H 0.0323 0.3822 -0.2041 0.055 Uiso 1 1 calc R . . H12C H 0.1557 0.3573 -0.1754 0.055 Uiso 1 1 calc R . . C13 C 0.0136(2) 0.2697(3) 0.0094(3) 0.0381(7) Uani 1 1 d . . . H13A H 0.0175 0.1952 0.0634 0.057 Uiso 1 1 calc R B . H13B H -0.0577 0.2766 -0.0488 0.057 Uiso 1 1 calc R . . H13C H 0.0304 0.3477 0.0600 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0295(3) 0.0202(3) 0.0149(3) -0.0019(2) 0.0077(2) -0.0010(2) N1 0.0321(12) 0.0210(9) 0.0144(10) -0.0014(8) 0.0083(9) -0.0009(8) N2 0.0324(12) 0.0218(10) 0.0161(11) -0.0027(8) 0.0025(9) 0.0022(8) O1 0.0363(10) 0.0304(9) 0.0169(9) -0.0062(7) 0.0141(8) -0.0007(7) O2 0.0373(11) 0.0286(9) 0.0258(10) -0.0027(7) 0.0111(8) -0.0092(8) O3 0.0408(11) 0.0259(9) 0.0236(10) -0.0002(7) 0.0037(8) 0.0066(8) O4 0.0296(10) 0.0297(9) 0.0165(9) -0.0037(7) 0.0019(7) 0.0032(7) C1 0.0318(14) 0.0270(12) 0.0138(12) -0.0023(9) 0.0107(11) 0.0017(10) C2 0.029(2) 0.024(3) 0.015(2) -0.0004(19) 0.0068(17) 0.0033(17) C3 0.033(2) 0.020(2) 0.016(2) -0.0010(16) 0.0096(18) 0.0013(16) C4 0.026(2) 0.025(2) 0.021(2) -0.0017(18) 0.0083(17) 0.0021(17) C5 0.030(2) 0.024(2) 0.020(2) -0.0006(17) 0.0086(16) 0.0018(16) C6 0.027(2) 0.032(2) 0.025(3) 0.006(2) 0.006(2) 0.0004(19) C7 0.031(3) 0.033(3) 0.031(3) -0.002(2) 0.004(2) -0.003(2) C2' 0.027(3) 0.025(3) 0.019(3) 0.001(2) 0.007(2) 0.003(2) C3' 0.027(2) 0.023(2) 0.016(3) 0.002(2) 0.0063(19) 0.002(2) C4' 0.025(3) 0.023(3) 0.016(3) 0.001(2) 0.006(2) 0.001(2) C5' 0.028(2) 0.026(3) 0.019(3) -0.001(2) 0.0069(19) 0.0019(19) C6' 0.028(3) 0.031(3) 0.020(3) 0.001(3) 0.004(3) -0.002(3) C7' 0.030(4) 0.031(4) 0.020(3) -0.007(3) 0.002(3) -0.004(4) C8 0.0351(14) 0.0231(11) 0.0158(13) -0.0043(9) 0.0011(11) 0.0024(10) C9 0.0281(13) 0.0256(12) 0.0154(12) 0.0006(9) 0.0067(10) -0.0013(10) C10 0.0260(13) 0.0366(13) 0.0147(13) 0.0006(10) 0.0032(11) 0.0015(10) C11 0.0379(16) 0.0470(16) 0.0214(15) -0.0064(12) 0.0027(12) -0.0020(13) C12 0.0442(18) 0.0438(16) 0.0195(14) 0.0057(12) 0.0060(13) 0.0008(13) C13 0.0340(16) 0.0625(19) 0.0200(14) -0.0025(13) 0.0116(12) 0.0044(14) _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 S1 O2 1.4255(18) . ? S1 O1 1.4277(17) . ? S1 N1 1.630(2) . ? S1 N2 1.683(2) . ? N1 C4' 1.440(11) . ? N1 C1 1.493(3) . ? N1 C4 1.526(7) . ? N2 C9 1.381(3) . ? N2 C8 1.475(3) . ? O3 C9 1.203(3) . ? O4 C9 1.335(3) . ? O4 C10 1.495(3) . ? C1 C2' 1.519(13) . ? C1 C2 1.529(8) . ? C1 C8 1.531(3) . ? C2 C3 1.532(5) . ? C3 C5 1.522(5) . ? C3 C4 1.534(5) . ? C5 C6 1.500(5) . ? C6 C7 1.313(5) . ? C2' C3' 1.534(6) . ? C3' C5' 1.525(6) . ? C3' C4' 1.534(6) . ? C5' C6' 1.501(6) . ? C6' C7' 1.309(5) . ? C10 C12 1.508(4) . ? C10 C13 1.510(4) . ? C10 C11 1.515(4) . ? 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 S1 O1 118.49(10) . . ? O2 S1 N1 109.79(11) . . ? O1 S1 N1 110.68(11) . . ? O2 S1 N2 108.78(11) . . ? O1 S1 N2 111.28(10) . . ? N1 S1 N2 95.37(10) . . ? C4' N1 C1 110.1(3) . . ? C4' N1 C4 10.7(7) . . ? C1 N1 C4 105.3(2) . . ? C4' N1 S1 123.1(4) . . ? C1 N1 S1 108.41(15) . . ? C4 N1 S1 118.0(2) . . ? C9 N2 C8 120.67(19) . . ? C9 N2 S1 124.39(16) . . ? C8 N2 S1 111.99(15) . . ? C9 O4 C10 120.13(18) . . ? N1 C1 C2' 105.0(4) . . ? N1 C1 C2 103.3(3) . . ? C2' C1 C2 7.7(11) . . ? N1 C1 C8 105.97(18) . . ? C2' C1 C8 109.1(8) . . ? C2 C1 C8 116.6(4) . . ? C1 C2 C3 107.8(4) . . ? C5 C3 C2 115.0(4) . . ? C5 C3 C4 112.9(4) . . ? C2 C3 C4 103.5(4) . . ? N1 C4 C3 100.6(4) . . ? C6 C5 C3 112.1(4) . . ? C7 C6 C5 124.0(4) . . ? C1 C2' C3' 103.6(7) . . ? C5' C3' C2' 113.8(6) . . ? C5' C3' C4' 113.0(5) . . ? C2' C3' C4' 103.8(5) . . ? N1 C4' C3' 106.8(6) . . ? C6' C5' C3' 110.8(6) . . ? C7' C6' C5' 125.2(7) . . ? N2 C8 C1 105.55(18) . . ? O3 C9 O4 127.4(2) . . ? O3 C9 N2 122.1(2) . . ? O4 C9 N2 110.5(2) . . ? O4 C10 C12 109.6(2) . . ? O4 C10 C13 109.6(2) . . ? C12 C10 C13 113.3(2) . . ? O4 C10 C11 102.0(2) . . ? C12 C10 C11 111.4(2) . . ? C13 C10 C11 110.3(2) . . ? 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 S1 N1 C4' 145.6(5) . . . . ? O1 S1 N1 C4' 12.9(5) . . . . ? N2 S1 N1 C4' -102.2(5) . . . . ? O2 S1 N1 C1 -83.95(17) . . . . ? O1 S1 N1 C1 143.38(15) . . . . ? N2 S1 N1 C1 28.23(17) . . . . ? O2 S1 N1 C4 156.6(3) . . . . ? O1 S1 N1 C4 23.9(3) . . . . ? N2 S1 N1 C4 -91.2(3) . . . . ? O2 S1 N2 C9 -57.5(2) . . . . ? O1 S1 N2 C9 74.8(2) . . . . ? N1 S1 N2 C9 -170.5(2) . . . . ? O2 S1 N2 C8 103.12(19) . . . . ? O1 S1 N2 C8 -124.58(18) . . . . ? N1 S1 N2 C8 -9.91(19) . . . . ? C4' N1 C1 C2' -16.0(10) . . . . ? C4 N1 C1 C2' -26.1(8) . . . . ? S1 N1 C1 C2' -153.3(8) . . . . ? C4' N1 C1 C2 -23.8(7) . . . . ? C4 N1 C1 C2 -33.9(5) . . . . ? S1 N1 C1 C2 -161.1(4) . . . . ? C4' N1 C1 C8 99.3(6) . . . . ? C4 N1 C1 C8 89.3(3) . . . . ? S1 N1 C1 C8 -37.9(2) . . . . ? N1 C1 C2 C3 9.8(7) . . . . ? C2' C1 C2 C3 -93(3) . . . . ? C8 C1 C2 C3 -106.0(6) . . . . ? C1 C2 C3 C5 141.1(5) . . . . ? C1 C2 C3 C4 17.5(7) . . . . ? C4' N1 C4 C3 -73(2) . . . . ? C1 N1 C4 C3 44.9(4) . . . . ? S1 N1 C4 C3 166.0(3) . . . . ? C5 C3 C4 N1 -162.0(4) . . . . ? C2 C3 C4 N1 -37.0(6) . . . . ? C2 C3 C5 C6 57.4(7) . . . . ? C4 C3 C5 C6 175.9(4) . . . . ? C3 C5 C6 C7 -114.0(6) . . . . ? N1 C1 C2' C3' 29.9(12) . . . . ? C2 C1 C2' C3' 109(3) . . . . ? C8 C1 C2' C3' -83.3(10) . . . . ? C1 C2' C3' C5' -155.7(9) . . . . ? C1 C2' C3' C4' -32.4(12) . . . . ? C1 N1 C4' C3' -4.7(9) . . . . ? C4 N1 C4' C3' 60.5(19) . . . . ? S1 N1 C4' C3' 125.1(5) . . . . ? C5' C3' C4' N1 147.1(8) . . . . ? C2' C3' C4' N1 23.2(11) . . . . ? C2' C3' C5' C6' -62.2(12) . . . . ? C4' C3' C5' C6' 179.7(8) . . . . ? C3' C5' C6' C7' 112.1(10) . . . . ? C9 N2 C8 C1 150.5(2) . . . . ? S1 N2 C8 C1 -10.9(2) . . . . ? N1 C1 C8 N2 29.7(3) . . . . ? C2' C1 C8 N2 142.2(3) . . . . ? C2 C1 C8 N2 144.0(3) . . . . ? C10 O4 C9 O3 -13.0(4) . . . . ? C10 O4 C9 N2 168.60(19) . . . . ? C8 N2 C9 O3 10.6(4) . . . . ? S1 N2 C9 O3 169.66(19) . . . . ? C8 N2 C9 O4 -170.8(2) . . . . ? S1 N2 C9 O4 -11.8(3) . . . . ? C9 O4 C10 C12 69.2(3) . . . . ? C9 O4 C10 C13 -55.7(3) . . . . ? C9 O4 C10 C11 -172.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.413 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.063