# 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 Yoshiji Takemoto' _publ_contact_author_email takemoto@pharm.kyoto-u.ac.jp _publ_section_title ; Platinum Catalyzed 7-endo Cyclization of Internal Alkynyl Amides and its Application to Synthesis of the Caprazamycin Core ; # Attachment '- compound9_CIF.cif' #TrackingRef '- compound9_CIF.cif' _audit_creation_date 2012-03-01 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? loop_ _publ_author_name C.Tsukano S.Yokouchi A.-L.Girard T.Kuribayashi S.Sakamoto ; T.Enomoto ; Y.Takemoto #============================================================================== data_SC1060 _database_code_depnum_ccdc_archive 'CCDC 869849' #TrackingRef '- compound9_CIF.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H21 N3 O5 S' _chemical_formula_moiety 'C24 H21 N3 O5 S' _chemical_formula_weight 463.51 _chemical_melting_point ? _chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 6.95676(13) _cell_length_b 12.7545(3) _cell_length_c 24.6435(5) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 2186.61(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 13313 _cell_measurement_theta_min 3.59 _cell_measurement_theta_max 68.25 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.010 _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968.00 _exptl_absorpt_coefficient_mu 1.680 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.630 _exptl_absorpt_correction_T_max 0.983 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 15573 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_theta_max 68.20 _diffrn_reflns_theta_full 68.20 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3984 _reflns_number_gt 3705 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0627 _refine_ls_number_restraints ? _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3984 _refine_ls_number_parameters 321 _refine_ls_goodness_of_fit_ref 1.829 _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/\s^2^(Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.473 _refine_diff_density_min -0.704 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 5(4) _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1664 Friedel Pairs' _refine_ls_abs_structure_Flack 0.021(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.3331 0.5567 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.80459(9) 0.59424(4) 0.85367(2) 0.02801(16) Uani 1.0 4 d . . . O1 O 1.1975(3) 0.79253(10) 0.76441(6) 0.0311(5) Uani 1.0 4 d . . . O2 O 0.6144(3) 0.59957(10) 0.87567(6) 0.0314(5) Uani 1.0 4 d . . . O3 O 0.9018(2) 0.49530(9) 0.84925(5) 0.0307(5) Uani 1.0 4 d . . . O4 O 1.4971(3) 0.86515(11) 0.97449(6) 0.0387(6) Uani 1.0 4 d . . . O5 O 1.2596(3) 0.97399(12) 0.98490(7) 0.0508(6) Uani 1.0 4 d . . . N1 N 0.7957(3) 0.64372(11) 0.79254(6) 0.0243(5) Uani 1.0 4 d . . . N2 N 0.9450(3) 0.80824(12) 0.70721(7) 0.0251(6) Uani 1.0 4 d . . . N3 N 1.3270(4) 0.88955(15) 0.97021(7) 0.0364(7) Uani 1.0 4 d . . . C2 C 1.1953(4) 0.81423(16) 0.94366(8) 0.0283(7) Uani 1.0 4 d . . . C3 C 1.0467(4) 0.75642(15) 0.74600(9) 0.0229(7) Uani 1.0 4 d . . . C4 C 0.7548(3) 0.78712(14) 0.68956(9) 0.0227(7) Uani 1.0 4 d . . . C5 C 0.7150(4) 0.81360(14) 0.63201(8) 0.0258(7) Uani 1.0 4 d . . . C6 C 1.3215(4) 0.50678(14) 0.72192(9) 0.0273(7) Uani 1.0 4 d . . . C7 C 0.6657(3) 0.73367(15) 0.78320(8) 0.0285(7) Uani 1.0 4 d . . . C8 C 1.2176(4) 0.57646(15) 0.63753(9) 0.0319(8) Uani 1.0 4 d . . . C9 C 0.8582(4) 0.81195(15) 0.59278(9) 0.0322(8) Uani 1.0 4 d . . . C10 C 1.5006(4) 0.48435(15) 0.69994(9) 0.0300(7) Uani 1.0 4 d . . . C11 C 1.1464(4) 0.64957(16) 0.90054(8) 0.0292(7) Uani 1.0 4 d . . . C12 C 0.9559(4) 0.67749(15) 0.89178(8) 0.0250(7) Uani 1.0 4 d . . . C13 C 0.9822(4) 0.64598(14) 0.76296(8) 0.0250(7) Uani 1.0 4 d . . . C14 C 0.9799(3) 0.56932(14) 0.71462(8) 0.0250(7) Uani 1.0 4 d . . . C15 C 0.5305(4) 0.84323(15) 0.61700(9) 0.0314(7) Uani 1.0 4 d . . . C16 C 1.2674(4) 0.71959(17) 0.92697(8) 0.0318(8) Uani 1.0 4 d . . . C17 C 1.5372(4) 0.50852(15) 0.64640(10) 0.0343(8) Uani 1.0 4 d . . . C18 C 0.6281(3) 0.74662(14) 0.72379(8) 0.0256(7) Uani 1.0 4 d . . . C19 C 1.0064(4) 0.84229(16) 0.93618(8) 0.0318(8) Uani 1.0 4 d . . . C20 C 0.8851(4) 0.77319(16) 0.90990(8) 0.0299(7) Uani 1.0 4 d . . . C21 C 0.6316(4) 0.86579(17) 0.52506(10) 0.0442(9) Uani 1.0 4 d . . . C22 C 0.8172(4) 0.83787(17) 0.53957(9) 0.0428(9) Uani 1.0 4 d . . . C23 C 1.3975(4) 0.55598(17) 0.61534(10) 0.0386(8) Uani 1.0 4 d . . . C24 C 0.4889(4) 0.86867(16) 0.56350(9) 0.0395(8) Uani 1.0 4 d . . . C1 C 1.1783(4) 0.55165(14) 0.69091(9) 0.0223(6) Uani 1.0 4 d . . . H1 H 1.0077 0.8632 0.6899 0.0309 Uiso 1.0 4 calc R . . H2 H 1.2964 0.4903 0.7580 0.0330 Uiso 1.0 4 calc R . . H3 H 0.7253 0.7965 0.7976 0.0337 Uiso 1.0 4 calc R . . H4 H 0.5471 0.7199 0.8026 0.0343 Uiso 1.0 4 calc R . . H5 H 1.1217 0.6062 0.6162 0.0382 Uiso 1.0 4 calc R . . H6 H 0.9820 0.7921 0.6027 0.0385 Uiso 1.0 4 calc R . . H7 H 1.5956 0.4539 0.7213 0.0360 Uiso 1.0 4 calc R . . H8 H 1.1912 0.5848 0.8886 0.0346 Uiso 1.0 4 calc R . . H9 H 1.0797 0.6197 0.7882 0.0298 Uiso 1.0 4 calc R . . H10 H 0.8995 0.5977 0.6860 0.0297 Uiso 1.0 4 calc R . . H11 H 0.9305 0.5015 0.7257 0.0299 Uiso 1.0 4 calc R . . H12 H 0.4345 0.8452 0.6432 0.0371 Uiso 1.0 4 calc R . . H13 H 1.3953 0.7024 0.9333 0.0382 Uiso 1.0 4 calc R . . H14 H 1.6564 0.4928 0.6314 0.0412 Uiso 1.0 4 calc R . . H15 H 0.5106 0.7248 0.7097 0.0304 Uiso 1.0 4 calc R . . H16 H 0.9604 0.9061 0.9490 0.0379 Uiso 1.0 4 calc R . . H17 H 0.7571 0.7903 0.9035 0.0358 Uiso 1.0 4 calc R . . H18 H 0.6032 0.8823 0.4892 0.0529 Uiso 1.0 4 calc R . . H19 H 0.9144 0.8377 0.5137 0.0512 Uiso 1.0 4 calc R . . H20 H 1.4237 0.5741 0.5796 0.0461 Uiso 1.0 4 calc R . . H21 H 0.3642 0.8875 0.5541 0.0470 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0330(4) 0.0197(3) 0.0314(4) 0.0030(3) 0.0038(3) 0.0028(3) O1 0.0267(10) 0.0271(8) 0.0395(10) -0.0035(8) -0.0042(9) -0.0052(7) O2 0.0246(10) 0.0284(8) 0.0413(10) 0.0034(8) 0.0101(8) 0.0057(8) O3 0.0375(10) 0.0176(7) 0.0370(10) 0.0057(7) 0.0068(9) 0.0029(7) O4 0.0337(12) 0.0448(10) 0.0375(10) 0.0022(9) -0.0051(10) 0.0041(8) O5 0.0515(14) 0.0413(10) 0.0595(13) 0.0005(10) 0.0098(11) -0.0242(9) N1 0.0251(12) 0.0213(9) 0.0265(11) 0.0044(9) 0.0027(10) 0.0035(8) N2 0.0256(12) 0.0193(10) 0.0304(12) -0.0037(9) 0.0005(10) 0.0045(8) N3 0.0473(16) 0.0378(12) 0.0242(12) -0.0028(12) 0.0046(12) -0.0008(9) C2 0.0332(16) 0.0297(13) 0.0221(12) -0.0030(13) 0.0017(12) -0.0030(10) C3 0.0259(15) 0.0198(12) 0.0230(13) 0.0012(11) 0.0040(11) -0.0046(10) C4 0.0215(14) 0.0137(10) 0.0329(14) 0.0020(10) -0.0016(12) 0.0008(9) C5 0.0326(16) 0.0158(11) 0.0291(14) -0.0015(11) -0.0004(12) -0.0006(9) C6 0.0307(16) 0.0180(11) 0.0334(15) -0.0012(11) 0.0037(13) 0.0015(10) C7 0.0308(16) 0.0216(11) 0.0331(14) 0.0063(11) 0.0023(12) 0.0004(10) C8 0.0313(16) 0.0342(13) 0.0302(15) 0.0047(12) -0.0046(12) -0.0021(10) C9 0.0381(18) 0.0257(12) 0.0327(14) 0.0046(11) 0.0007(13) 0.0002(11) C10 0.0250(16) 0.0206(11) 0.0445(16) 0.0009(11) -0.0028(13) -0.0029(11) C11 0.0407(18) 0.0245(12) 0.0225(13) 0.0080(12) 0.0033(12) -0.0035(10) C12 0.0320(15) 0.0198(11) 0.0231(12) 0.0054(11) 0.0025(11) 0.0025(10) C13 0.0245(15) 0.0208(12) 0.0298(14) 0.0008(11) 0.0021(12) 0.0012(10) C14 0.0243(15) 0.0178(11) 0.0329(14) -0.0021(10) 0.0001(12) 0.0021(10) C15 0.0329(16) 0.0255(12) 0.0359(15) 0.0030(12) -0.0016(13) -0.0003(11) C16 0.0337(17) 0.0379(13) 0.0239(14) 0.0094(13) 0.0044(12) 0.0035(10) C17 0.0301(16) 0.0316(13) 0.0412(15) 0.0010(12) 0.0093(14) -0.0102(12) C18 0.0282(15) 0.0160(11) 0.0326(14) 0.0011(10) -0.0066(12) 0.0003(10) C19 0.0408(18) 0.0238(12) 0.0307(14) 0.0063(13) 0.0051(13) -0.0011(11) C20 0.0333(17) 0.0279(12) 0.0285(14) 0.0040(12) 0.0027(12) 0.0011(10) C21 0.063(3) 0.0423(15) 0.0273(16) 0.0082(15) -0.0048(15) 0.0021(12) C22 0.057(2) 0.0392(14) 0.0325(15) 0.0062(15) 0.0012(15) 0.0026(12) C23 0.0388(18) 0.0479(15) 0.0290(16) 0.0005(14) 0.0043(14) -0.0042(12) C24 0.047(2) 0.0354(14) 0.0362(15) 0.0060(13) -0.0129(14) 0.0011(12) C1 0.0245(14) 0.0146(10) 0.0278(13) -0.0007(10) 0.0033(12) -0.0017(9) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 O2 1.4316(17) yes . . S1 O3 1.4357(14) yes . . S1 N1 1.6345(16) yes . . S1 C12 1.766(3) yes . . O1 C3 1.232(3) yes . . O4 N3 1.228(3) yes . . O5 N3 1.229(3) yes . . N1 C7 1.479(3) yes . . N1 C13 1.489(3) yes . . N2 C3 1.361(3) yes . . N2 C4 1.419(3) yes . . N3 C2 1.480(3) yes . . C2 C16 1.370(3) yes . . C2 C19 1.374(4) yes . . C3 C13 1.536(3) yes . . C4 C5 1.484(3) yes . . C4 C18 1.325(3) yes . . C5 C9 1.388(4) yes . . C5 C15 1.389(4) yes . . C6 C10 1.389(4) yes . . C6 C1 1.380(3) yes . . C7 C18 1.496(3) yes . . C8 C23 1.391(4) yes . . C8 C1 1.380(4) yes . . C9 C22 1.382(4) yes . . C10 C17 1.379(4) yes . . C11 C12 1.389(4) yes . . C11 C16 1.389(3) yes . . C12 C20 1.390(3) yes . . C13 C14 1.541(3) yes . . C14 C1 1.515(3) yes . . C15 C24 1.388(4) yes . . C17 C23 1.377(4) yes . . C19 C20 1.381(3) yes . . C21 C22 1.386(4) yes . . C21 C24 1.373(4) yes . . N2 H1 0.930 no . . C6 H2 0.930 no . . C7 H3 0.970 no . . C7 H4 0.970 no . . C8 H5 0.930 no . . C9 H6 0.930 no . . C10 H7 0.930 no . . C11 H8 0.930 no . . C13 H9 0.980 no . . C14 H10 0.970 no . . C14 H11 0.970 no . . C15 H12 0.930 no . . C16 H13 0.930 no . . C17 H14 0.930 no . . C18 H15 0.930 no . . C19 H16 0.930 no . . C20 H17 0.930 no . . C21 H18 0.930 no . . C22 H19 0.930 no . . C23 H20 0.930 no . . C24 H21 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O2 S1 O3 120.37(9) yes . . . O2 S1 N1 107.19(9) yes . . . O2 S1 C12 108.72(10) yes . . . O3 S1 N1 106.70(8) yes . . . O3 S1 C12 106.76(10) yes . . . N1 S1 C12 106.30(9) yes . . . S1 N1 C7 117.79(13) yes . . . S1 N1 C13 115.19(13) yes . . . C7 N1 C13 116.22(15) yes . . . C3 N2 C4 127.47(18) yes . . . O4 N3 O5 124.4(2) yes . . . O4 N3 C2 118.05(19) yes . . . O5 N3 C2 117.5(2) yes . . . N3 C2 C16 118.5(3) yes . . . N3 C2 C19 118.84(19) yes . . . C16 C2 C19 122.6(2) yes . . . O1 C3 N2 121.33(18) yes . . . O1 C3 C13 119.41(19) yes . . . N2 C3 C13 118.99(19) yes . . . N2 C4 C5 115.07(19) yes . . . N2 C4 C18 120.0(2) yes . . . C5 C4 C18 125.0(2) yes . . . C4 C5 C9 121.9(2) yes . . . C4 C5 C15 119.3(2) yes . . . C9 C5 C15 118.8(2) yes . . . C10 C6 C1 121.2(2) yes . . . N1 C7 C18 110.17(16) yes . . . C23 C8 C1 120.7(3) yes . . . C5 C9 C22 120.6(3) yes . . . C6 C10 C17 119.5(2) yes . . . C12 C11 C16 119.1(2) yes . . . S1 C12 C11 119.81(16) yes . . . S1 C12 C20 119.19(18) yes . . . C11 C12 C20 120.9(2) yes . . . N1 C13 C3 113.92(16) yes . . . N1 C13 C14 110.92(16) yes . . . C3 C13 C14 111.99(17) yes . . . C13 C14 C1 112.52(17) yes . . . C5 C15 C24 120.6(3) yes . . . C2 C16 C11 119.0(3) yes . . . C10 C17 C23 120.0(3) yes . . . C4 C18 C7 123.3(2) yes . . . C2 C19 C20 118.7(2) yes . . . C12 C20 C19 119.6(3) yes . . . C22 C21 C24 120.2(3) yes . . . C9 C22 C21 119.9(3) yes . . . C8 C23 C17 119.9(3) yes . . . C15 C24 C21 119.9(3) yes . . . C6 C1 C8 118.7(3) yes . . . C6 C1 C14 120.4(2) yes . . . C8 C1 C14 120.9(2) yes . . . C3 N2 H1 116.394 no . . . C4 N2 H1 116.129 no . . . C10 C6 H2 119.648 no . . . C1 C6 H2 119.189 no . . . N1 C7 H3 108.809 no . . . N1 C7 H4 107.624 no . . . C18 C7 H3 109.970 no . . . C18 C7 H4 110.766 no . . . H3 C7 H4 109.449 no . . . C23 C8 H5 119.965 no . . . C1 C8 H5 119.368 no . . . C5 C9 H6 119.065 no . . . C22 C9 H6 120.331 no . . . C6 C10 H7 120.168 no . . . C17 C10 H7 120.291 no . . . C12 C11 H8 119.875 no . . . C16 C11 H8 121.040 no . . . N1 C13 H9 106.586 no . . . C3 C13 H9 106.528 no . . . C14 C13 H9 106.351 no . . . C13 C14 H10 109.329 no . . . C13 C14 H11 110.564 no . . . C1 C14 H10 107.504 no . . . C1 C14 H11 107.398 no . . . H10 C14 H11 109.432 no . . . C5 C15 H12 119.099 no . . . C24 C15 H12 120.289 no . . . C2 C16 H13 120.469 no . . . C11 C16 H13 120.516 no . . . C10 C17 H14 119.838 no . . . C23 C17 H14 120.180 no . . . C4 C18 H15 117.670 no . . . C7 C18 H15 118.984 no . . . C2 C19 H16 120.721 no . . . C20 C19 H16 120.537 no . . . C12 C20 H17 119.366 no . . . C19 C20 H17 120.988 no . . . C22 C21 H18 120.047 no . . . C24 C21 H18 119.794 no . . . C9 C22 H19 120.037 no . . . C21 C22 H19 120.059 no . . . C8 C23 H20 120.210 no . . . C17 C23 H20 119.841 no . . . C15 C24 H21 119.498 no . . . C21 C24 H21 120.593 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O2 S1 N1 C7 36.32(13) no . . . . O2 S1 N1 C13 179.43(9) no . . . . O2 S1 C12 C11 145.29(13) no . . . . O2 S1 C12 C20 -38.45(17) no . . . . O3 S1 N1 C7 166.52(11) no . . . . O3 S1 N1 C13 -50.37(12) no . . . . O3 S1 C12 C11 14.02(17) no . . . . O3 S1 C12 C20 -169.72(13) no . . . . N1 S1 C12 C11 -99.60(15) no . . . . N1 S1 C12 C20 76.66(16) no . . . . C12 S1 N1 C7 -79.82(14) no . . . . C12 S1 N1 C13 63.29(12) no . . . . S1 N1 C7 C18 -162.11(11) no . . . . S1 N1 C13 C3 -120.60(13) no . . . . S1 N1 C13 C14 111.94(13) no . . . . C7 N1 C13 C3 23.1(3) no . . . . C7 N1 C13 C14 -104.35(16) no . . . . C13 N1 C7 C18 55.2(2) no . . . . C3 N2 C4 C5 -149.77(18) no . . . . C3 N2 C4 C18 30.2(3) no . . . . C4 N2 C3 O1 -167.39(18) no . . . . C4 N2 C3 C13 18.6(3) no . . . . O4 N3 C2 C16 2.4(3) no . . . . O4 N3 C2 C19 -176.92(16) no . . . . O5 N3 C2 C16 -179.98(17) no . . . . O5 N3 C2 C19 0.7(3) no . . . . N3 C2 C16 C11 -178.08(16) no . . . . N3 C2 C19 C20 178.03(16) no . . . . C16 C2 C19 C20 -1.2(3) no . . . . C19 C2 C16 C11 1.2(3) no . . . . O1 C3 C13 N1 117.7(2) no . . . . O1 C3 C13 C14 -115.4(2) no . . . . N2 C3 C13 N1 -68.2(3) no . . . . N2 C3 C13 C14 58.7(3) no . . . . N2 C4 C5 C9 28.4(3) no . . . . N2 C4 C5 C15 -150.14(16) no . . . . N2 C4 C18 C7 8.1(3) no . . . . C5 C4 C18 C7 -171.92(16) no . . . . C18 C4 C5 C9 -151.60(18) no . . . . C18 C4 C5 C15 29.9(3) no . . . . C4 C5 C9 C22 -179.44(15) no . . . . C4 C5 C15 C24 179.87(15) no . . . . C9 C5 C15 C24 1.3(3) no . . . . C15 C5 C9 C22 -0.9(3) no . . . . C10 C6 C1 C8 -1.5(3) no . . . . C10 C6 C1 C14 176.18(16) no . . . . C1 C6 C10 C17 0.9(3) no . . . . N1 C7 C18 C4 -75.6(2) no . . . . C23 C8 C1 C6 0.4(3) no . . . . C23 C8 C1 C14 -177.27(17) no . . . . C1 C8 C23 C17 1.3(3) no . . . . C5 C9 C22 C21 -0.0(3) no . . . . C6 C10 C17 C23 0.9(3) no . . . . C12 C11 C16 C2 0.0(3) no . . . . C16 C11 C12 S1 175.06(16) no . . . . C16 C11 C12 C20 -1.1(3) no . . . . S1 C12 C20 C19 -175.13(13) no . . . . C11 C12 C20 C19 1.1(3) no . . . . N1 C13 C14 C1 -167.67(13) no . . . . C3 C13 C14 C1 63.8(2) no . . . . C13 C14 C1 C6 62.7(2) no . . . . C13 C14 C1 C8 -119.68(18) no . . . . C5 C15 C24 C21 -0.8(3) no . . . . C10 C17 C23 C8 -2.0(3) no . . . . C2 C19 C20 C12 0.1(3) no . . . . C22 C21 C24 C15 -0.2(3) no . . . . C24 C21 C22 C9 0.6(4) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 N1 3.449(3) no . . O1 C4 3.591(3) no . . O1 C14 3.450(3) no . . O1 C1 3.569(3) no . . O2 C7 2.871(3) no . . O2 C20 3.027(3) no . . O3 C11 2.892(3) no . . O3 C13 2.920(3) no . . O3 C14 3.492(3) no . . O4 C16 2.715(3) no . . O4 C19 3.554(3) no . . O5 C16 3.545(3) no . . O5 C19 2.714(3) no . . N1 N2 3.147(3) no . . N1 C4 3.141(3) no . . N1 C20 3.388(3) no . . N2 C7 2.861(3) no . . N2 C9 2.884(3) no . . N2 C14 3.062(3) no . . C2 C12 2.729(3) no . . C3 C7 2.820(4) no . . C3 C18 2.966(4) no . . C3 C1 3.082(3) no . . C4 C13 3.003(3) no . . C4 C14 3.248(3) no . . C5 C21 2.780(4) no . . C6 C13 3.122(3) no . . C6 C23 2.752(4) no . . C7 C12 3.428(3) no . . C7 C14 3.469(3) no . . C7 C20 3.512(3) no . . C8 C10 2.761(4) no . . C9 C24 2.765(4) no . . C11 C13 3.578(3) no . . C11 C19 2.786(3) no . . C12 C13 3.205(3) no . . C13 C18 2.941(3) no . . C14 C18 3.340(3) no . . C15 C18 2.984(3) no . . C15 C22 2.761(4) no . . C16 C20 2.778(4) no . . C17 C1 2.782(4) no . . O1 C7 3.374(3) no . 1_655 O1 C10 3.342(3) no . 3_856 O1 C18 3.212(3) no . 1_655 O2 C11 3.374(3) no . 1_455 O2 C15 3.426(3) no . 3_646 O2 C16 3.126(3) no . 1_455 O2 C24 3.382(3) no . 3_646 O3 N2 2.961(2) no . 3_746 O3 C5 3.563(3) no . 3_746 O3 C9 3.209(3) no . 3_746 O4 C2 3.347(3) no . 2_567 O4 C11 3.255(3) no . 2_567 O4 C12 3.352(3) no . 2_567 O4 C16 3.256(3) no . 2_567 O4 C17 3.504(3) no . 3_856 O4 C19 3.442(3) no . 2_567 O4 C20 3.346(3) no . 1_655 O4 C20 3.441(3) no . 2_567 O4 C23 3.371(3) no . 3_856 O5 C17 3.558(3) no . 3_856 O5 C21 3.544(3) no . 4_675 O5 C23 3.590(3) no . 3_856 O5 C24 3.281(3) no . 4_675 N2 O3 2.961(2) no . 3_756 N2 C6 3.591(3) no . 3_756 N3 C17 3.384(3) no . 3_856 N3 C23 3.553(4) no . 3_856 C2 O4 3.347(3) no . 2_467 C4 C6 3.590(3) no . 3_756 C5 O3 3.563(3) no . 3_756 C6 N2 3.591(3) no . 3_746 C6 C4 3.590(3) no . 3_746 C6 C7 3.487(3) no . 3_746 C6 C18 3.595(3) no . 3_746 C7 O1 3.374(3) no . 1_455 C7 C6 3.487(3) no . 3_756 C7 C10 3.425(3) no . 3_756 C9 O3 3.209(3) no . 3_756 C10 O1 3.342(3) no . 3_846 C10 C7 3.425(3) no . 3_746 C10 C14 3.525(3) no . 1_655 C10 C18 3.510(3) no . 1_655 C11 O2 3.374(3) no . 1_655 C11 O4 3.255(3) no . 2_467 C12 O4 3.352(3) no . 2_467 C14 C10 3.525(3) no . 1_455 C14 C17 3.594(4) no . 1_455 C15 O2 3.426(3) no . 3_656 C16 O2 3.126(3) no . 1_655 C16 O4 3.256(3) no . 2_467 C17 O4 3.504(3) no . 3_846 C17 O5 3.558(3) no . 3_846 C17 N3 3.384(3) no . 3_846 C17 C14 3.594(4) no . 1_655 C18 O1 3.212(3) no . 1_455 C18 C6 3.595(3) no . 3_756 C18 C10 3.510(3) no . 1_455 C19 O4 3.442(3) no . 2_467 C20 O4 3.346(3) no . 1_455 C20 O4 3.441(3) no . 2_467 C21 O5 3.544(3) no . 4_674 C23 O4 3.371(3) no . 3_846 C23 O5 3.590(3) no . 3_846 C23 N3 3.553(4) no . 3_846 C24 O2 3.382(3) no . 3_656 C24 O5 3.281(3) no . 4_674 S1 H3 2.9782 no . . S1 H4 2.7129 no . . S1 H8 2.8264 no . . S1 H9 2.5237 no . . S1 H11 3.4797 no . . S1 H17 2.8050 no . . O1 H1 2.4350 no . . O1 H3 3.3856 no . . O1 H9 2.4240 no . . O2 H3 3.2569 no . . O2 H4 2.4112 no . . O2 H17 2.7151 no . . O3 H2 3.5494 no . . O3 H8 2.5098 no . . O3 H9 2.5122 no . . O3 H11 3.0518 no . . O4 H13 2.4160 no . . O5 H16 2.4213 no . . N1 H10 2.7852 no . . N1 H11 2.6232 no . . N1 H15 3.0275 no . . N1 H17 3.3229 no . . N2 H3 2.7053 no . . N2 H6 2.5973 no . . N2 H9 3.2633 no . . N2 H10 2.7541 no . . N2 H15 3.2043 no . . N3 H13 2.5975 no . . N3 H16 2.6120 no . . C2 H8 3.2250 no . . C2 H17 3.2194 no . . C3 H3 2.6224 no . . C3 H6 3.5896 no . . C3 H10 2.7080 no . . C3 H11 3.3872 no . . C4 H3 2.6730 no . . C4 H4 3.2541 no . . C4 H6 2.6621 no . . C4 H10 2.6189 no . . C4 H12 2.6112 no . . C5 H1 2.5654 no . . C5 H10 3.3170 no . . C5 H15 2.6411 no . . C5 H19 3.2440 no . . C5 H21 3.2460 no . . C6 H5 3.2136 no . . C6 H9 2.7520 no . . C6 H10 3.2780 no . . C6 H11 2.7223 no . . C6 H14 3.2310 no . . C7 H9 3.2290 no . . C7 H10 3.3749 no . . C7 H17 3.1166 no . . C8 H2 3.2127 no . . C8 H6 3.3144 no . . C8 H10 2.5294 no . . C8 H11 3.1024 no . . C8 H14 3.2375 no . . C9 H1 2.6899 no . . C9 H5 3.2529 no . . C9 H10 3.5820 no . . C9 H12 3.2275 no . . C9 H18 3.2355 no . . C10 H20 3.2247 no . . C11 H9 2.8318 no . . C11 H17 3.2495 no . . C12 H3 3.2037 no . . C12 H9 2.7922 no . . C12 H13 3.2398 no . . C12 H16 3.2394 no . . C13 H1 3.3094 no . . C13 H2 2.9555 no . . C13 H3 2.7585 no . . C13 H4 3.3181 no . . C13 H8 3.5084 no . . C14 H2 2.6466 no . . C14 H5 2.6604 no . . C15 H6 3.2274 no . . C15 H15 2.7431 no . . C15 H18 3.2290 no . . C16 H16 3.2427 no . . C17 H2 3.2285 no . . C17 H5 3.2342 no . . C18 H1 3.1443 no . . C18 H10 2.8355 no . . C18 H12 2.7085 no . . C19 H13 3.2419 no . . C20 H3 2.9970 no . . C20 H8 3.2527 no . . C21 H6 3.2379 no . . C21 H12 3.2298 no . . C22 H21 3.2343 no . . C23 H7 3.2274 no . . C24 H19 3.2290 no . . C1 H7 3.2471 no . . C1 H9 2.6413 no . . C1 H20 3.2449 no . . H1 H3 3.4104 no . . H1 H6 2.3399 no . . H1 H10 3.4709 no . . H2 H7 2.3161 no . . H2 H8 3.5146 no . . H2 H9 2.3563 no . . H2 H10 3.5561 no . . H2 H11 2.6704 no . . H3 H9 3.3493 no . . H3 H15 2.7848 no . . H3 H17 2.6201 no . . H4 H15 2.3040 no . . H4 H17 3.0195 no . . H5 H6 2.5839 no . . H5 H10 2.3159 no . . H5 H11 3.2920 no . . H5 H20 2.3232 no . . H6 H10 3.2702 no . . H6 H19 2.3174 no . . H7 H14 2.3106 no . . H8 H9 2.6300 no . . H8 H13 2.3412 no . . H9 H10 2.8279 no . . H9 H11 2.3924 no . . H10 H15 3.2079 no . . H12 H15 2.3076 no . . H12 H21 2.3152 no . . H14 H20 2.3078 no . . H16 H17 2.3329 no . . H18 H19 2.3180 no . . H18 H21 2.3079 no . . S1 H1 3.3968 no . 3_746 S1 H12 3.5859 no . 3_646 O1 H4 2.7674 no . 1_655 O1 H7 2.5359 no . 3_856 O1 H11 2.8210 no . 3_756 O1 H12 3.4763 no . 1_655 O1 H15 2.7025 no . 1_655 O2 H8 2.9674 no . 1_455 O2 H12 3.2950 no . 3_646 O2 H13 2.4624 no . 1_455 O2 H21 3.2146 no . 3_646 O3 H1 2.0406 no . 3_746 O3 H6 2.9629 no . 3_746 O3 H12 3.0280 no . 3_646 O3 H21 3.3150 no . 3_646 O4 H14 3.2551 no . 3_856 O4 H16 3.3251 no . 1_655 O4 H17 2.6917 no . 1_655 O4 H20 3.0300 no . 3_856 O5 H14 2.9342 no . 3_856 O5 H18 3.1215 no . 4_675 O5 H19 3.3784 no . 4_775 O5 H20 3.0012 no . 3_856 O5 H21 2.6009 no . 4_675 N1 H7 3.2986 no . 1_455 N2 H2 2.9908 no . 3_756 N2 H11 3.0918 no . 3_756 N3 H14 2.8308 no . 3_856 N3 H20 3.1704 no . 3_856 C2 H14 3.1097 no . 3_856 C3 H11 3.2068 no . 3_756 C3 H15 3.3726 no . 1_655 C4 H2 2.9174 no . 3_756 C5 H2 3.5259 no . 3_756 C5 H8 3.5571 no . 3_756 C6 H3 2.7439 no . 3_746 C6 H15 3.0911 no . 1_655 C7 H2 3.4368 no . 3_756 C7 H7 3.3471 no . 3_756 C8 H15 3.3021 no . 1_655 C8 H16 3.2866 no . 3_746 C8 H18 3.2650 no . 2_566 C9 H8 3.5275 no . 3_756 C10 H3 2.8659 no . 3_746 C10 H4 3.3898 no . 3_746 C10 H10 3.1476 no . 1_655 C10 H11 3.0653 no . 1_655 C10 H15 3.0774 no . 1_655 C14 H1 3.5293 no . 3_746 C14 H7 3.0571 no . 1_455 C14 H14 3.1983 no . 1_455 C16 H17 3.5713 no . 1_655 C17 H3 3.5428 no . 3_746 C17 H10 2.9323 no . 1_655 C17 H11 3.3639 no . 1_655 C17 H15 3.1753 no . 1_655 C18 H2 3.1836 no . 3_756 C18 H7 3.3523 no . 3_756 C19 H13 3.3558 no . 2_467 C19 H14 3.4584 no . 3_856 C20 H13 3.5715 no . 1_455 C21 H5 3.4999 no . 2_466 C21 H16 3.5193 no . 4_674 C21 H19 3.1513 no . 2_466 C21 H20 3.3711 no . 2_466 C22 H18 3.5135 no . 2_566 C22 H20 3.2290 no . 2_466 C23 H15 3.2665 no . 1_655 C23 H16 3.5166 no . 3_746 C23 H17 3.5856 no . 3_746 C23 H18 3.3830 no . 2_566 C23 H19 3.4583 no . 2_566 C24 H19 3.2886 no . 2_466 C1 H3 3.3345 no . 3_746 C1 H15 3.2309 no . 1_655 H1 S1 3.3968 no . 3_756 H1 O3 2.0406 no . 3_756 H1 C14 3.5293 no . 3_756 H1 H2 2.9584 no . 3_756 H1 H9 3.3708 no . 3_756 H1 H11 2.7608 no . 3_756 H1 H12 3.1915 no . 1_655 H2 N2 2.9908 no . 3_746 H2 C4 2.9174 no . 3_746 H2 C5 3.5259 no . 3_746 H2 C7 3.4368 no . 3_746 H2 C18 3.1836 no . 3_746 H2 H1 2.9584 no . 3_746 H2 H3 2.8295 no . 3_746 H2 H4 3.5820 no . 1_655 H2 H12 3.5852 no . 3_746 H2 H15 3.5473 no . 1_655 H3 C6 2.7439 no . 3_756 H3 C10 2.8659 no . 3_756 H3 C17 3.5428 no . 3_756 H3 C1 3.3345 no . 3_756 H3 H2 2.8295 no . 3_756 H3 H7 3.0380 no . 3_756 H3 H11 3.5915 no . 3_756 H4 O1 2.7674 no . 1_455 H4 C10 3.3898 no . 3_756 H4 H2 3.5820 no . 1_455 H4 H7 3.1999 no . 3_756 H4 H9 3.5113 no . 1_455 H4 H13 3.3968 no . 1_455 H5 C21 3.4999 no . 2_566 H5 H14 3.5654 no . 1_455 H5 H16 3.0691 no . 3_746 H5 H18 2.6040 no . 2_566 H6 O3 2.9629 no . 3_756 H6 H12 3.3717 no . 1_655 H6 H18 3.2830 no . 2_566 H6 H21 3.1606 no . 1_655 H7 O1 2.5359 no . 3_846 H7 N1 3.2986 no . 1_655 H7 C7 3.3471 no . 3_746 H7 C14 3.0571 no . 1_655 H7 C18 3.3523 no . 3_746 H7 H3 3.0380 no . 3_746 H7 H4 3.1999 no . 3_746 H7 H10 2.9310 no . 1_655 H7 H11 2.4105 no . 1_655 H7 H15 3.5175 no . 1_655 H7 H15 3.4592 no . 3_746 H8 O2 2.9674 no . 1_655 H8 C5 3.5571 no . 3_746 H8 C9 3.5275 no . 3_746 H9 H1 3.3708 no . 3_746 H9 H4 3.5113 no . 1_655 H10 C10 3.1476 no . 1_455 H10 C17 2.9323 no . 1_455 H10 H7 2.9310 no . 1_455 H10 H14 2.5425 no . 1_455 H11 O1 2.8210 no . 3_746 H11 N2 3.0918 no . 3_746 H11 C3 3.2068 no . 3_746 H11 C10 3.0653 no . 1_455 H11 C17 3.3639 no . 1_455 H11 H1 2.7608 no . 3_746 H11 H3 3.5915 no . 3_746 H11 H7 2.4105 no . 1_455 H11 H14 3.0093 no . 1_455 H12 S1 3.5859 no . 3_656 H12 O1 3.4763 no . 1_455 H12 O2 3.2950 no . 3_656 H12 O3 3.0280 no . 3_656 H12 H1 3.1915 no . 1_455 H12 H2 3.5852 no . 3_756 H12 H6 3.3717 no . 1_455 H13 O2 2.4624 no . 1_655 H13 C19 3.3558 no . 2_567 H13 C20 3.5715 no . 1_655 H13 H4 3.3968 no . 1_655 H13 H16 3.2447 no . 2_567 H13 H17 2.8514 no . 1_655 H14 O4 3.2551 no . 3_846 H14 O5 2.9342 no . 3_846 H14 N3 2.8308 no . 3_846 H14 C2 3.1097 no . 3_846 H14 C14 3.1983 no . 1_655 H14 C19 3.4584 no . 3_846 H14 H5 3.5654 no . 1_655 H14 H10 2.5425 no . 1_655 H14 H11 3.0093 no . 1_655 H14 H16 3.5004 no . 3_846 H15 O1 2.7025 no . 1_455 H15 C3 3.3726 no . 1_455 H15 C6 3.0911 no . 1_455 H15 C8 3.3021 no . 1_455 H15 C10 3.0774 no . 1_455 H15 C17 3.1753 no . 1_455 H15 C23 3.2665 no . 1_455 H15 C1 3.2309 no . 1_455 H15 H2 3.5473 no . 1_455 H15 H7 3.5175 no . 1_455 H15 H7 3.4592 no . 3_756 H16 O4 3.3251 no . 1_455 H16 C8 3.2866 no . 3_756 H16 C21 3.5193 no . 4_675 H16 C23 3.5166 no . 3_756 H16 H5 3.0691 no . 3_756 H16 H13 3.2447 no . 2_467 H16 H14 3.5004 no . 3_856 H16 H18 2.9088 no . 4_675 H16 H20 3.4970 no . 3_756 H17 O4 2.6917 no . 1_455 H17 C16 3.5713 no . 1_455 H17 C23 3.5856 no . 3_756 H17 H13 2.8514 no . 1_455 H18 O5 3.1215 no . 4_674 H18 C8 3.2650 no . 2_466 H18 C22 3.5135 no . 2_466 H18 C23 3.3830 no . 2_466 H18 H5 2.6040 no . 2_466 H18 H6 3.2830 no . 2_466 H18 H16 2.9088 no . 4_674 H18 H19 3.0988 no . 2_466 H18 H20 2.8548 no . 2_466 H19 O5 3.3784 no . 4_774 H19 C21 3.1513 no . 2_566 H19 C23 3.4583 no . 2_466 H19 C24 3.2886 no . 2_566 H19 H18 3.0988 no . 2_566 H19 H20 2.5585 no . 2_466 H19 H21 3.3444 no . 1_655 H19 H21 3.3412 no . 2_566 H20 O4 3.0300 no . 3_846 H20 O5 3.0012 no . 3_846 H20 N3 3.1704 no . 3_846 H20 C21 3.3711 no . 2_566 H20 C22 3.2290 no . 2_566 H20 H16 3.4970 no . 3_746 H20 H18 2.8548 no . 2_566 H20 H19 2.5585 no . 2_566 H21 O2 3.2146 no . 3_656 H21 O3 3.3150 no . 3_656 H21 O5 2.6009 no . 4_674 H21 H6 3.1606 no . 1_455 H21 H19 3.3444 no . 1_455 H21 H19 3.3412 no . 2_466 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H1 O3 . . 3_756 2.961(2) 0.930 2.041 169.9 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================