Supplementary material (ESI) for New Journal of Chemistry This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Watkinson, Michael' 'Griffiths, D.' 'Motevalli, Majid' 'Ronketti, Fiona' 'Scheuermann, J.Erik W.' _publ_contact_author_name 'Dr Michael Watkinson' _publ_contact_author_address ; Chemistry Queen Mary, University of London Mile End Road London E1 4NS UNITED KINGDOM ; _publ_contact_author_email 'm.watkinson@qmul.ac.uk' _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; The synthesis C2-symmetric 1,4,7-triazacyclononane ligands derived from chiral aziridines ; data_valmco2 _database_code_CSD 185531 _audit_creation_date 2002-05-10T13:22:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C33 H39 N3 O6 S3' _chemical_formula_sum 'C33 H45 N3 O6 S3' _chemical_formula_weight 675.9 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 11.261(2) _cell_length_b 13.805(3) _cell_length_c 21.546(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3349.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.234 _cell_measurement_theta_max 12.78 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.34 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.27 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_T_max 0.9735 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.52066E-1 _diffrn_orient_matrix_ub_12 -0.42089E-1 _diffrn_orient_matrix_ub_13 -0.26171E-1 _diffrn_orient_matrix_ub_21 0.20104E-1 _diffrn_orient_matrix_ub_22 0.03986 _diffrn_orient_matrix_ub_23 -0.37288E-1 _diffrn_orient_matrix_ub_31 0.06912 _diffrn_orient_matrix_ub_32 -0.43425E-1 _diffrn_orient_matrix_ub_33 -0.8759E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 3 _diffrn_standards_decay_corr_max 1.104 _diffrn_standards_decay_corr_min 0.977 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 0 -10 0 -7 -3 _diffrn_reflns_av_R_equivalents 0.0047 _diffrn_reflns_av_unetI/netI 0.196 _diffrn_reflns_number 3415 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3319 _reflns_number_gt 1753 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4/PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4/PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0416P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3319 _refine_ls_number_parameters 413 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1912 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.18(19) _refine_diff_density_max 0.481 _refine_diff_density_min -0.44 _refine_diff_density_rms 0.092 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.8683(2) 0.74130(17) 0.95701(10) 0.0238(5) Uani 1 1 d . . . S2 S 1.2042(2) 0.53522(19) 0.79022(11) 0.0281(6) Uani 1 1 d . . . S3 S 0.9904(2) 0.32360(16) 0.94723(11) 0.0266(6) Uani 1 1 d . . . N1 N 0.9052(6) 0.6536(5) 0.9109(3) 0.0185(17) Uani 1 1 d . . . N2 N 1.1543(6) 0.5604(5) 0.8595(3) 0.0213(18) Uani 1 1 d . . . N3 N 0.9851(6) 0.4417(5) 0.9360(3) 0.0222(17) Uani 1 1 d . . . O1 O 0.8161(5) 0.6980(4) 1.0112(3) 0.0302(16) Uani 1 1 d . . . O2 O 0.9719(5) 0.8012(4) 0.9630(3) 0.0317(16) Uani 1 1 d . . . O3 O 1.2641(5) 0.4434(5) 0.7943(3) 0.0355(18) Uani 1 1 d . . . O4 O 1.2656(6) 0.6173(5) 0.7646(3) 0.0425(19) Uani 1 1 d . . . O5 O 0.8853(6) 0.2821(4) 0.9201(3) 0.0355(18) Uani 1 1 d . . . O6 O 1.1053(5) 0.2936(4) 0.9253(3) 0.0297(17) Uani 1 1 d . . . C1 C 0.9847(8) 0.6803(7) 0.8594(4) 0.029(2) Uani 1 1 d . . . H1A H 0.9732 0.7499 0.8501 0.035 Uiso 1 1 calc R . . H1B H 0.9604 0.6434 0.8221 0.035 Uiso 1 1 calc R . . C2 C 1.1187(8) 0.6621(6) 0.8709(4) 0.023(2) Uani 1 1 d . . . H2A H 1.1654 0.7051 0.8433 0.028 Uiso 1 1 calc R . . H2B H 1.138 0.6795 0.9143 0.028 Uiso 1 1 calc R . . C3 C 1.1946(8) 0.5022(6) 0.9133(4) 0.024(2) Uani 1 1 d . . . H3 H 1.2122 0.4353 0.8979 0.029 Uiso 1 1 calc R . . C4 C 1.0909(7) 0.4946(6) 0.9594(4) 0.021(2) Uani 1 1 d . . . H4A H 1.1196 0.4617 0.9974 0.025 Uiso 1 1 calc R . . H4B H 1.0662 0.5609 0.9713 0.025 Uiso 1 1 calc R . . C5 C 0.8709(8) 0.4876(6) 0.9534(4) 0.025(2) Uani 1 1 d . . . H5A H 0.8798 0.5169 0.9951 0.03 Uiso 1 1 calc R . . H5B H 0.8097 0.4364 0.9566 0.03 Uiso 1 1 calc R . . C6 C 0.8264(8) 0.5648(6) 0.9093(4) 0.026(2) Uani 1 1 d . . . H6 H 0.749 0.5866 0.9272 0.031 Uiso 1 1 calc R . . C7 C 1.3070(7) 0.5403(6) 0.9453(4) 0.025(2) Uani 1 1 d . . . H7 H 1.2827 0.5953 0.9728 0.03 Uiso 1 1 calc R . . C8 C 1.3599(9) 0.4636(7) 0.9858(5) 0.043(3) Uani 1 1 d . . . H8A H 1.3797 0.4068 0.9605 0.065 Uiso 1 1 calc R . . H8B H 1.3026 0.445 1.0179 0.065 Uiso 1 1 calc R . . H8C H 1.4321 0.4886 1.0055 0.065 Uiso 1 1 calc R . . C9 C 1.3999(8) 0.5788(7) 0.9003(5) 0.038(3) Uani 1 1 d . . . H9A H 1.4244 0.5268 0.8721 0.057 Uiso 1 1 calc R . . H9B H 1.4691 0.6019 0.9236 0.057 Uiso 1 1 calc R . . H9C H 1.3662 0.6323 0.8762 0.057 Uiso 1 1 calc R . . C10 C 0.7968(9) 0.5316(7) 0.8436(4) 0.034(2) Uani 1 1 d . . . H10 H 0.8725 0.516 0.8215 0.041 Uiso 1 1 calc R . . C11 C 0.7189(9) 0.4419(7) 0.8441(5) 0.047(3) Uani 1 1 d . . . H11A H 0.6573 0.449 0.876 0.071 Uiso 1 1 calc R . . H11B H 0.7675 0.3849 0.8534 0.071 Uiso 1 1 calc R . . H11C H 0.6814 0.4339 0.8034 0.071 Uiso 1 1 calc R . . C12 C 0.7310(8) 0.6129(7) 0.8072(4) 0.038(3) Uani 1 1 d . . . H12A H 0.6504 0.6204 0.8237 0.057 Uiso 1 1 calc R . . H12B H 0.7267 0.5953 0.7631 0.057 Uiso 1 1 calc R . . H12C H 0.7743 0.674 0.8117 0.057 Uiso 1 1 calc R . . C13 C 0.7584(8) 0.8103(6) 0.9211(4) 0.023(2) Uani 1 1 d . . . C14 C 0.7869(8) 0.8924(7) 0.8879(4) 0.029(2) Uani 1 1 d . . . H14 H 0.8675 0.9121 0.8846 0.035 Uiso 1 1 calc R . . C15 C 0.6989(8) 0.9466(7) 0.8595(4) 0.031(2) Uani 1 1 d . . . H15 H 0.7198 1.0047 0.8385 0.037 Uiso 1 1 calc R . . C16 C 0.5827(8) 0.9183(7) 0.8609(5) 0.031(3) Uani 1 1 d . . . C17 C 0.5534(8) 0.8346(7) 0.8951(4) 0.030(2) Uani 1 1 d . . . H17 H 0.4728 0.8146 0.8973 0.036 Uiso 1 1 calc R . . C18 C 0.6388(8) 0.7812(6) 0.9255(4) 0.021(2) Uani 1 1 d . . . H18 H 0.6174 0.7257 0.949 0.025 Uiso 1 1 calc R . . C19 C 0.4888(9) 0.9750(7) 0.8284(4) 0.038(3) Uani 1 1 d . . . H19A H 0.5231 1.0069 0.7919 0.058 Uiso 1 1 calc R . . H19B H 0.4567 1.0241 0.8566 0.058 Uiso 1 1 calc R . . H19C H 0.425 0.9313 0.8152 0.058 Uiso 1 1 calc R . . C20 C 1.0795(7) 0.5179(7) 0.7425(4) 0.023(2) Uani 1 1 d U . . C21 C 1.0510(8) 0.5852(7) 0.6977(4) 0.033(3) Uani 1 1 d . . . H21 H 1.0926 0.645 0.696 0.039 Uiso 1 1 calc R . . C22 C 0.9606(9) 0.5656(8) 0.6546(5) 0.042(3) Uani 1 1 d . . . H22 H 0.9424 0.6119 0.6233 0.05 Uiso 1 1 calc R . . C23 C 0.8995(9) 0.4814(9) 0.6572(5) 0.042(3) Uani 1 1 d . . . C24 C 0.9240(9) 0.4168(8) 0.7035(5) 0.043(3) Uani 1 1 d . . . H24 H 0.8783 0.3592 0.7068 0.051 Uiso 1 1 calc R . . C25 C 1.0156(8) 0.4340(7) 0.7461(5) 0.032(2) Uani 1 1 d U . . H25 H 1.0331 0.3876 0.7774 0.038 Uiso 1 1 calc R . . C26 C 0.8104(10) 0.4543(10) 0.6068(5) 0.076(5) Uani 1 1 d . . . H26A H 0.8527 0.4272 0.5711 0.115 Uiso 1 1 calc R . . H26B H 0.7667 0.5123 0.5939 0.115 Uiso 1 1 calc R . . H26C H 0.7546 0.4062 0.6231 0.115 Uiso 1 1 calc R . . C28 C 0.9856(9) 0.3020(6) 1.0284(4) 0.028(2) Uani 1 1 d . . . C29 C 0.8776(8) 0.2914(6) 1.0580(5) 0.030(2) Uani 1 1 d . . . H29 H 0.8055 0.2979 1.0355 0.036 Uiso 1 1 calc R . . C30 C 0.8757(9) 0.2712(7) 1.1210(4) 0.034(3) Uani 1 1 d . . . H30 H 0.8018 0.2623 1.1415 0.041 Uiso 1 1 calc R . . C31 C 0.9805(9) 0.2640(6) 1.1544(4) 0.029(2) Uani 1 1 d . . . C32 C 1.0859(8) 0.2766(6) 1.1232(5) 0.030(3) Uani 1 1 d . . . H32 H 1.1582 0.2727 1.1458 0.036 Uiso 1 1 calc R . . C33 C 1.0906(8) 0.2946(6) 1.0607(4) 0.030(3) Uani 1 1 d . . . H33 H 1.1647 0.3018 1.0402 0.037 Uiso 1 1 calc R . . C34 C 0.9788(10) 0.2391(7) 1.2232(4) 0.045(3) Uani 1 1 d . . . H34A H 1.0325 0.2827 1.2456 0.067 Uiso 1 1 calc R . . H34B H 1.0048 0.172 1.2289 0.067 Uiso 1 1 calc R . . H34C H 0.8979 0.2467 1.2393 0.067 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 0.0269(13) 0.0237(13) 0.0209(12) -0.0014(12) -0.0007(12) 0.0025(11) S2 0.0254(13) 0.0380(16) 0.0208(13) -0.0039(12) 0.0025(12) 0.0012(13) S3 0.0278(14) 0.0202(12) 0.0316(14) -0.0006(12) 0.0011(12) -0.0006(12) N1 0.020(4) 0.013(4) 0.022(4) -0.002(3) -0.002(4) 0.002(3) N2 0.026(4) 0.021(4) 0.017(4) -0.002(3) 0.008(3) 0.000(4) N3 0.023(4) 0.020(4) 0.023(4) 0.001(3) -0.002(4) 0.000(4) O1 0.033(4) 0.029(4) 0.029(4) 0.011(3) 0.002(3) 0.000(3) O2 0.030(4) 0.029(4) 0.037(4) -0.006(3) -0.007(3) -0.004(3) O3 0.034(4) 0.041(4) 0.032(4) -0.012(3) 0.003(3) 0.014(3) O4 0.038(4) 0.060(5) 0.029(4) -0.005(4) 0.010(3) -0.031(4) O5 0.037(4) 0.029(4) 0.041(4) -0.004(3) -0.006(4) -0.003(3) O6 0.026(4) 0.022(4) 0.041(4) -0.002(3) 0.011(3) 0.003(3) C1 0.032(5) 0.031(5) 0.024(5) 0.001(5) 0.018(5) -0.003(5) C2 0.028(5) 0.015(5) 0.027(5) 0.000(4) 0.004(5) -0.007(5) C3 0.025(5) 0.019(5) 0.029(5) 0.002(4) -0.006(5) 0.000(4) C4 0.025(5) 0.019(5) 0.019(5) -0.004(4) 0.005(4) 0.001(4) C5 0.022(5) 0.028(5) 0.024(5) -0.004(5) 0.012(5) -0.008(4) C6 0.030(6) 0.022(5) 0.027(5) 0.004(4) 0.006(4) 0.002(4) C7 0.025(5) 0.024(5) 0.026(5) -0.003(5) -0.001(5) 0.003(4) C8 0.035(6) 0.046(7) 0.048(7) 0.000(6) -0.013(6) -0.007(6) C9 0.024(6) 0.046(7) 0.044(7) -0.004(5) -0.002(5) -0.009(5) C10 0.034(5) 0.027(6) 0.043(6) -0.005(5) -0.018(5) 0.010(5) C11 0.042(7) 0.038(7) 0.061(8) -0.012(6) -0.019(6) 0.000(6) C12 0.034(6) 0.045(7) 0.036(6) -0.001(5) -0.010(5) 0.017(6) C13 0.030(5) 0.011(5) 0.028(5) -0.009(4) 0.001(4) 0.006(4) C14 0.029(6) 0.033(6) 0.025(5) 0.003(5) 0.000(5) 0.006(5) C15 0.028(6) 0.041(7) 0.023(5) 0.003(5) 0.005(5) -0.005(5) C16 0.028(6) 0.029(6) 0.036(7) -0.003(5) 0.013(5) 0.001(5) C17 0.024(5) 0.034(6) 0.033(6) -0.003(5) 0.003(5) -0.002(5) C18 0.022(5) 0.014(5) 0.027(5) 0.003(4) 0.007(4) -0.006(4) C19 0.042(6) 0.029(6) 0.045(6) 0.006(5) 0.019(6) 0.000(6) C20 0.023(5) 0.026(5) 0.021(5) -0.010(5) 0.002(4) 0.007(4) C21 0.028(6) 0.037(7) 0.033(6) 0.000(5) 0.010(5) 0.013(5) C22 0.040(7) 0.053(8) 0.032(6) -0.004(6) -0.005(5) 0.012(6) C23 0.024(6) 0.069(9) 0.033(6) -0.021(6) -0.006(5) 0.018(6) C24 0.033(6) 0.044(7) 0.051(7) -0.030(6) 0.001(6) 0.002(5) C25 0.028(6) 0.036(5) 0.032(5) -0.014(5) 0.018(5) 0.008(5) C26 0.041(7) 0.122(12) 0.067(9) -0.055(9) -0.026(7) 0.028(8) C28 0.032(6) 0.019(5) 0.034(6) 0.004(4) -0.004(5) 0.001(5) C29 0.014(5) 0.026(6) 0.049(7) 0.009(5) 0.006(5) -0.004(4) C30 0.032(6) 0.037(7) 0.034(6) 0.010(5) 0.016(5) -0.006(5) C31 0.034(6) 0.015(5) 0.038(6) -0.002(5) 0.002(5) -0.002(5) C32 0.020(5) 0.028(6) 0.042(7) 0.002(5) -0.010(5) -0.001(4) C33 0.027(5) 0.028(6) 0.037(7) 0.009(5) 0.001(5) -0.001(4) C34 0.046(7) 0.047(6) 0.042(6) 0.008(6) -0.006(5) 0.000(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.436(6) . ? S1 O1 1.438(6) . ? S1 N1 1.621(7) . ? S1 C13 1.744(9) . ? S2 O4 1.438(7) . ? S2 O3 1.439(6) . ? S2 N2 1.633(7) . ? S2 C20 1.756(9) . ? S3 O5 1.438(7) . ? S3 O6 1.438(6) . ? S3 N3 1.649(7) . ? S3 C28 1.775(9) . ? N1 C1 1.473(10) . ? N1 C6 1.514(10) . ? N2 C2 1.481(10) . ? N2 C3 1.481(10) . ? N3 C5 1.482(10) . ? N3 C4 1.485(10) . ? C1 C2 1.550(12) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C7 1.535(11) . ? C3 C4 1.537(11) . ? C3 H3 1 . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.513(11) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C10 1.525(12) . ? C6 H6 1 . ? C7 C8 1.497(11) . ? C7 C9 1.523(12) . ? C7 H7 1 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 C11 1.518(12) . ? C10 C12 1.557(12) . ? C10 H10 1 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 C14 1.377(12) . ? C13 C18 1.408(11) . ? C14 C15 1.384(12) . ? C14 H14 0.95 . ? C15 C16 1.366(12) . ? C15 H15 0.95 . ? C16 C17 1.410(12) . ? C16 C19 1.490(13) . ? C17 C18 1.377(12) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 C25 1.366(12) . ? C20 C21 1.377(12) . ? C21 C22 1.405(12) . ? C21 H21 0.95 . ? C22 C23 1.353(14) . ? C22 H22 0.95 . ? C23 C24 1.366(14) . ? C23 C26 1.524(13) . ? C24 C25 1.402(13) . ? C24 H24 0.95 . ? C25 H25 0.95 . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C28 C33 1.376(12) . ? C28 C29 1.382(12) . ? C29 C30 1.386(12) . ? C29 H29 0.95 . ? C30 C31 1.385(13) . ? C30 H30 0.95 . ? C31 C32 1.375(12) . ? C31 C34 1.522(12) . ? C32 C33 1.370(12) . ? C32 H32 0.95 . ? C33 H33 0.95 . ? C34 H34A 0.98 . ? C34 H34B 0.98 . ? C34 H34C 0.98 . ? 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 119.9(4) . . ? O2 S1 N1 106.1(4) . . ? O1 S1 N1 107.0(4) . . ? O2 S1 C13 107.6(4) . . ? O1 S1 C13 107.3(4) . . ? N1 S1 C13 108.5(4) . . ? O4 S2 O3 119.5(4) . . ? O4 S2 N2 110.4(4) . . ? O3 S2 N2 107.1(4) . . ? O4 S2 C20 105.5(4) . . ? O3 S2 C20 106.9(4) . . ? N2 S2 C20 106.8(4) . . ? O5 S3 O6 119.5(3) . . ? O5 S3 N3 107.7(4) . . ? O6 S3 N3 105.7(4) . . ? O5 S3 C28 107.9(4) . . ? O6 S3 C28 107.6(4) . . ? N3 S3 C28 108.0(4) . . ? C1 N1 C6 122.8(7) . . ? C1 N1 S1 115.5(6) . . ? C6 N1 S1 118.0(6) . . ? C2 N2 C3 118.0(7) . . ? C2 N2 S2 116.4(6) . . ? C3 N2 S2 119.6(6) . . ? C5 N3 C4 113.6(6) . . ? C5 N3 S3 114.7(5) . . ? C4 N3 S3 114.0(5) . . ? N1 C1 C2 115.6(7) . . ? N1 C1 H1A 108.4 . . ? C2 C1 H1A 108.4 . . ? N1 C1 H1B 108.4 . . ? C2 C1 H1B 108.4 . . ? H1A C1 H1B 107.5 . . ? N2 C2 C1 113.0(7) . . ? N2 C2 H2A 109 . . ? C1 C2 H2A 109 . . ? N2 C2 H2B 109 . . ? C1 C2 H2B 109 . . ? H2A C2 H2B 107.8 . . ? N2 C3 C7 114.7(7) . . ? N2 C3 C4 108.0(7) . . ? C7 C3 C4 111.0(7) . . ? N2 C3 H3 107.6 . . ? C7 C3 H3 107.6 . . ? C4 C3 H3 107.6 . . ? N3 C4 C3 115.1(7) . . ? N3 C4 H4A 108.5 . . ? C3 C4 H4A 108.5 . . ? N3 C4 H4B 108.5 . . ? C3 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? N3 C5 C6 115.4(7) . . ? N3 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? N3 C5 H5B 108.4 . . ? C6 C5 H5B 108.4 . . ? H5A C5 H5B 107.5 . . ? N1 C6 C5 111.2(7) . . ? N1 C6 C10 113.1(7) . . ? C5 C6 C10 116.4(7) . . ? N1 C6 H6 105 . . ? C5 C6 H6 105 . . ? C10 C6 H6 105 . . ? C8 C7 C9 110.1(8) . . ? C8 C7 C3 110.3(7) . . ? C9 C7 C3 113.6(7) . . ? C8 C7 H7 107.5 . . ? C9 C7 H7 107.5 . . ? C3 C7 H7 107.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C6 111.3(8) . . ? C11 C10 C12 108.4(8) . . ? C6 C10 C12 110.9(8) . . ? C11 C10 H10 108.7 . . ? C6 C10 H10 108.7 . . ? C12 C10 H10 108.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 119.5(8) . . ? C14 C13 S1 120.9(7) . . ? C18 C13 S1 119.5(7) . . ? C13 C14 C15 120.5(9) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 121.4(10) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 118.0(9) . . ? C15 C16 C19 121.3(9) . . ? C17 C16 C19 120.7(8) . . ? C18 C17 C16 121.6(9) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C17 C18 C13 118.8(8) . . ? C17 C18 H18 120.6 . . ? C13 C18 H18 120.6 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 119.3(9) . . ? C25 C20 S2 120.2(8) . . ? C21 C20 S2 120.3(7) . . ? C20 C21 C22 120.2(10) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 120.4(10) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 119.3(10) . . ? C22 C23 C26 121.0(12) . . ? C24 C23 C26 119.5(12) . . ? C23 C24 C25 121.1(10) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C20 C25 C24 119.6(10) . . ? C20 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C33 C28 C29 120.9(8) . . ? C33 C28 S3 119.0(7) . . ? C29 C28 S3 120.0(8) . . ? C28 C29 C30 119.2(9) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C31 C30 C29 120.6(9) . . ? C31 C30 H30 119.7 . . ? C29 C30 H30 119.7 . . ? C32 C31 C30 118.3(8) . . ? C32 C31 C34 121.0(9) . . ? C30 C31 C34 120.7(9) . . ? C33 C32 C31 122.4(9) . . ? C33 C32 H32 118.8 . . ? C31 C32 H32 118.8 . . ? C32 C33 C28 118.6(9) . . ? C32 C33 H33 120.7 . . ? C28 C33 H33 120.7 . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? 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 O2 S1 N1 C1 -37.3(7) . . . . ? O1 S1 N1 C1 -166.4(6) . . . . ? C13 S1 N1 C1 78.1(7) . . . . ? O2 S1 N1 C6 163.8(6) . . . . ? O1 S1 N1 C6 34.6(7) . . . . ? C13 S1 N1 C6 -80.9(7) . . . . ? O4 S2 N2 C2 32.2(7) . . . . ? O3 S2 N2 C2 163.8(6) . . . . ? C20 S2 N2 C2 -82.0(7) . . . . ? O4 S2 N2 C3 -120.0(6) . . . . ? O3 S2 N2 C3 11.5(7) . . . . ? C20 S2 N2 C3 125.7(7) . . . . ? O5 S3 N3 C5 49.0(6) . . . . ? O6 S3 N3 C5 177.8(6) . . . . ? C28 S3 N3 C5 -67.3(7) . . . . ? O5 S3 N3 C4 -177.6(5) . . . . ? O6 S3 N3 C4 -48.9(6) . . . . ? C28 S3 N3 C4 66.0(7) . . . . ? C6 N1 C1 C2 -106.1(9) . . . . ? S1 N1 C1 C2 96.1(8) . . . . ? C3 N2 C2 C1 -113.8(8) . . . . ? S2 N2 C2 C1 93.5(7) . . . . ? N1 C1 C2 N2 81.9(9) . . . . ? C2 N2 C3 C7 -62.3(10) . . . . ? S2 N2 C3 C7 89.6(8) . . . . ? C2 N2 C3 C4 62.1(9) . . . . ? S2 N2 C3 C4 -146.0(6) . . . . ? C5 N3 C4 C3 -138.8(7) . . . . ? S3 N3 C4 C3 87.4(8) . . . . ? N2 C3 C4 N3 64.2(9) . . . . ? C7 C3 C4 N3 -169.2(7) . . . . ? C4 N3 C5 C6 87.3(9) . . . . ? S3 N3 C5 C6 -139.2(6) . . . . ? C1 N1 C6 C5 108.8(9) . . . . ? S1 N1 C6 C5 -93.9(7) . . . . ? C1 N1 C6 C10 -24.3(11) . . . . ? S1 N1 C6 C10 133.0(7) . . . . ? N3 C5 C6 N1 -68.3(9) . . . . ? N3 C5 C6 C10 63.2(10) . . . . ? N2 C3 C7 C8 -163.5(8) . . . . ? C4 C3 C7 C8 73.6(9) . . . . ? N2 C3 C7 C9 -39.4(11) . . . . ? C4 C3 C7 C9 -162.2(7) . . . . ? N1 C6 C10 C11 179.4(7) . . . . ? C5 C6 C10 C11 48.8(11) . . . . ? N1 C6 C10 C12 -59.8(10) . . . . ? C5 C6 C10 C12 169.6(8) . . . . ? O2 S1 C13 C14 19.2(8) . . . . ? O1 S1 C13 C14 149.5(7) . . . . ? N1 S1 C13 C14 -95.2(8) . . . . ? O2 S1 C13 C18 -161.4(7) . . . . ? O1 S1 C13 C18 -31.1(8) . . . . ? N1 S1 C13 C18 84.2(8) . . . . ? C18 C13 C14 C15 0.4(13) . . . . ? S1 C13 C14 C15 179.9(7) . . . . ? C13 C14 C15 C16 -3.0(14) . . . . ? C14 C15 C16 C17 3.4(14) . . . . ? C14 C15 C16 C19 -177.9(9) . . . . ? C15 C16 C17 C18 -1.3(14) . . . . ? C19 C16 C17 C18 -180.0(9) . . . . ? C16 C17 C18 C13 -1.2(14) . . . . ? C14 C13 C18 C17 1.6(13) . . . . ? S1 C13 C18 C17 -177.8(7) . . . . ? O4 S2 C20 C25 166.4(7) . . . . ? O3 S2 C20 C25 38.2(8) . . . . ? N2 S2 C20 C25 -76.1(7) . . . . ? O4 S2 C20 C21 -8.3(8) . . . . ? O3 S2 C20 C21 -136.5(7) . . . . ? N2 S2 C20 C21 109.2(7) . . . . ? C25 C20 C21 C22 -2.8(12) . . . . ? S2 C20 C21 C22 171.9(7) . . . . ? C20 C21 C22 C23 1.1(14) . . . . ? C21 C22 C23 C24 2.0(15) . . . . ? C21 C22 C23 C26 -173.5(9) . . . . ? C22 C23 C24 C25 -3.4(14) . . . . ? C26 C23 C24 C25 172.2(8) . . . . ? C21 C20 C25 C24 1.4(12) . . . . ? S2 C20 C25 C24 -173.3(7) . . . . ? C23 C24 C25 C20 1.7(13) . . . . ? O5 S3 C28 C33 151.8(7) . . . . ? O6 S3 C28 C33 21.6(9) . . . . ? N3 S3 C28 C33 -92.0(8) . . . . ? O5 S3 C28 C29 -27.2(8) . . . . ? O6 S3 C28 C29 -157.4(7) . . . . ? N3 S3 C28 C29 89.0(8) . . . . ? C33 C28 C29 C30 -1.2(13) . . . . ? S3 C28 C29 C30 177.8(7) . . . . ? C28 C29 C30 C31 1.5(14) . . . . ? C29 C30 C31 C32 -0.5(13) . . . . ? C29 C30 C31 C34 -178.3(9) . . . . ? C30 C31 C32 C33 -0.9(14) . . . . ? C34 C31 C32 C33 176.9(9) . . . . ? C31 C32 C33 C28 1.2(14) . . . . ? C29 C28 C33 C32 -0.1(13) . . . . ? S3 C28 C33 C32 -179.1(7) . . . . ? #===END data_vmco1 _database_code_CSD 185532 _audit_creation_date 2002-05-10T15:04:51-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H44 N3 O4 S2' _chemical_formula_sum 'C21 H28 N2 O2 S' _chemical_formula_weight 372.51 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.180(5) _cell_length_b 23.468(8) _cell_length_c 10.149(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1948.4(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.216 _cell_measurement_theta_max 12.408 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour transparent _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.27 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_factor_muR 0.037 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _exptl_absorpt_correction_T_min 0.7626 _exptl_absorpt_correction_T_max 0.9639 _exptl_absorpt_correction_T_ave 0.6477 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.11168E-1 _diffrn_orient_matrix_ub_12 -0.9626E-2 _diffrn_orient_matrix_ub_13 -0.09554 _diffrn_orient_matrix_ub_21 -0.12351E-1 _diffrn_orient_matrix_ub_22 0.41381E-1 _diffrn_orient_matrix_ub_23 -0.02144 _diffrn_orient_matrix_ub_31 0.121109 _diffrn_orient_matrix_ub_32 0.00326 _diffrn_orient_matrix_ub_33 -0.10969E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 3 _diffrn_standards_decay_corr_max 1.035 _diffrn_standards_decay_corr_min 0.974 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 10 -3 0 -2 -5 _diffrn_reflns_av_R_equivalents 0.0053 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_number 2031 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -2 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 1977 _reflns_number_gt 1753 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4/PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4/PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0675P)^2^+1.4465P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1977 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.087 _refine_ls_shift/su_mean 0.002 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(16) _refine_diff_density_max 0.337 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.23434(11) 0.82111(4) 0.64113(10) 0.0311(3) Uani 1 1 d . . . N1 N 0.3806(4) 0.86252(14) 0.6833(3) 0.0288(8) Uani 1 1 d . . . N2 N 0.6577(4) 0.92990(13) 0.6151(3) 0.0270(7) Uani 1 1 d . . . O1 O 0.2684(4) 0.76710(12) 0.6988(3) 0.0393(7) Uani 1 1 d . . . O2 O 0.0848(3) 0.85014(13) 0.6712(3) 0.0410(8) Uani 1 1 d . . . C1 C 0.2382(3) 0.81137(11) 0.46934(19) 0.0304(9) Uani 1 1 d G . . C2 C 0.3596(3) 0.77815(10) 0.4120(2) 0.0341(10) Uani 1 1 d G . . H2 H 0.4398 0.7615 0.4644 0.041 Uiso 1 1 calc R . . C3 C 0.3611(3) 0.76973(11) 0.2765(3) 0.0371(10) Uani 1 1 d G . . H3 H 0.4423 0.7475 0.2382 0.045 Uiso 1 1 calc R . . C4 C 0.2412(4) 0.79454(12) 0.19822(19) 0.0412(11) Uani 1 1 d G . . C5 C 0.1198(3) 0.82776(12) 0.2555(3) 0.0463(12) Uani 1 1 d G . . H5 H 0.0395 0.8444 0.2031 0.056 Uiso 1 1 calc R . . C6 C 0.1183(3) 0.83618(11) 0.3911(3) 0.0413(11) Uani 1 1 d G . . H6 H 0.0371 0.8584 0.4294 0.05 Uiso 1 1 calc R . . C7 C 0.2424(9) 0.7836(2) 0.0513(5) 0.0660(17) Uani 1 1 d . . . H7A H 0.3343 0.8025 0.0122 0.099 Uiso 1 1 calc R . . H7B H 0.1432 0.7978 0.013 0.099 Uiso 1 1 calc R . . H7C H 0.2504 0.7433 0.0354 0.099 Uiso 1 1 calc R . . C8 C 0.5485(4) 0.84124(18) 0.7047(4) 0.0314(9) Uani 1 1 d . . . H8A H 0.5497 0.8002 0.6941 0.038 Uiso 1 1 calc R . . H8B H 0.582 0.8499 0.7942 0.038 Uiso 1 1 calc R . . C9 C 0.6683(5) 0.86757(16) 0.6097(4) 0.0316(9) Uani 1 1 d . . . H9A H 0.7783 0.8556 0.6321 0.038 Uiso 1 1 calc R . . H9B H 0.6447 0.8546 0.521 0.038 Uiso 1 1 calc R . . C10 C 0.4927(4) 0.94653(17) 0.5736(4) 0.0259(8) Uani 1 1 d . . . H10A H 0.4696 0.9305 0.4876 0.031 Uiso 1 1 calc R . . H10B H 0.4866 0.9877 0.5664 0.031 Uiso 1 1 calc R . . C11 C 0.3667(4) 0.92592(15) 0.6712(4) 0.0251(8) Uani 1 1 d . . . H11 H 0.258 0.9349 0.6362 0.03 Uiso 1 1 calc R . . C12 C 0.3817(5) 0.95325(17) 0.8078(4) 0.0306(9) Uani 1 1 d . . . H12 H 0.4872 0.942 0.8455 0.037 Uiso 1 1 calc R . . C13 C 0.3777(7) 1.0180(2) 0.7985(5) 0.0474(12) Uani 1 1 d . . . H13A H 0.2808 1.0297 0.7525 0.071 Uiso 1 1 calc R . . H13B H 0.4724 1.0311 0.7516 0.071 Uiso 1 1 calc R . . H13C H 0.3774 1.034 0.8856 0.071 Uiso 1 1 calc R . . C14 C 0.2479(7) 0.9331(2) 0.8998(4) 0.0525(13) Uani 1 1 d . . . H14A H 0.266 0.9486 0.9862 0.079 Uiso 1 1 calc R . . H14B H 0.2491 0.8923 0.9044 0.079 Uiso 1 1 calc R . . H14C H 0.1438 0.9457 0.8673 0.079 Uiso 1 1 calc R . . C15 C 0.7831(5) 0.95664(17) 0.5331(4) 0.0341(9) Uani 1 1 d . . . H15A H 0.757 0.9502 0.4411 0.041 Uiso 1 1 calc R . . H15B H 0.8877 0.9387 0.5509 0.041 Uiso 1 1 calc R . . C16 C 0.7976(3) 1.02014(8) 0.5575(3) 0.0295(9) Uani 1 1 d G . . C17 C 0.8911(3) 1.03957(10) 0.6626(2) 0.0404(10) Uani 1 1 d G . . H17 H 0.9488 1.0138 0.7144 0.049 Uiso 1 1 calc R . . C18 C 0.8984(4) 1.09752(11) 0.6903(2) 0.0519(13) Uani 1 1 d G . . H18 H 0.961 1.1105 0.7607 0.062 Uiso 1 1 calc R . . C19 C 0.8122(4) 1.13604(8) 0.6129(3) 0.0461(12) Uani 1 1 d G . . H19 H 0.8171 1.1748 0.6314 0.055 Uiso 1 1 calc R . . C20 C 0.7187(3) 1.11660(9) 0.5077(3) 0.0409(10) Uani 1 1 d G . . H20 H 0.661 1.1424 0.4559 0.049 Uiso 1 1 calc R . . C21 C 0.7114(3) 1.05866(10) 0.4800(2) 0.0339(9) Uani 1 1 d G . . H21 H 0.6488 1.0457 0.4097 0.041 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 0.0191(4) 0.0305(5) 0.0438(5) 0.0034(4) 0.0011(4) -0.0024(4) N1 0.0171(15) 0.0282(16) 0.0410(19) -0.0014(15) -0.0036(15) 0.0037(13) N2 0.0159(14) 0.0294(16) 0.0356(18) -0.0003(14) 0.0009(14) 0.0024(13) O1 0.0338(16) 0.0347(15) 0.0495(16) 0.0088(13) 0.0021(15) -0.0037(14) O2 0.0180(13) 0.0476(19) 0.057(2) -0.0033(16) 0.0031(14) -0.0028(12) C1 0.0207(19) 0.0273(19) 0.043(2) 0.0022(16) -0.0021(19) -0.0062(17) C2 0.025(2) 0.031(2) 0.047(2) 0.0033(18) -0.007(2) 0.0019(18) C3 0.034(2) 0.031(2) 0.046(3) -0.0025(18) -0.004(2) 0.001(2) C4 0.049(3) 0.030(2) 0.045(2) -0.0002(18) -0.015(2) -0.005(2) C5 0.048(3) 0.038(3) 0.053(3) 0.003(2) -0.021(2) 0.008(2) C6 0.027(2) 0.042(2) 0.055(3) -0.002(2) -0.011(2) 0.009(2) C7 0.102(5) 0.048(3) 0.048(3) -0.002(2) -0.023(4) 0.014(4) C8 0.0194(18) 0.029(2) 0.045(2) 0.0011(18) -0.0037(18) 0.0031(16) C9 0.0205(18) 0.028(2) 0.046(2) -0.0010(18) -0.0011(17) 0.0059(16) C10 0.0186(18) 0.029(2) 0.0297(19) -0.0005(16) -0.0032(16) 0.0037(16) C11 0.0143(16) 0.0282(18) 0.033(2) 0.0022(16) -0.0024(16) 0.0032(14) C12 0.0225(19) 0.039(2) 0.0306(19) -0.0018(17) -0.0012(17) 0.0081(18) C13 0.045(3) 0.051(3) 0.045(3) -0.014(2) 0.004(2) -0.003(2) C14 0.065(3) 0.048(3) 0.045(2) -0.006(2) 0.021(3) 0.003(3) C15 0.0197(18) 0.042(2) 0.041(2) -0.0016(19) 0.0064(19) 0.0007(18) C16 0.0212(18) 0.036(2) 0.0310(19) 0.0022(17) 0.0087(17) -0.0018(16) C17 0.043(2) 0.043(2) 0.035(2) 0.0135(19) -0.004(2) -0.012(2) C18 0.071(3) 0.049(3) 0.036(2) 0.004(2) -0.008(3) -0.021(3) C19 0.056(3) 0.039(2) 0.044(2) 0.000(2) 0.013(2) -0.012(2) C20 0.034(2) 0.042(2) 0.047(2) 0.0087(19) 0.009(2) 0.002(2) C21 0.0227(19) 0.044(2) 0.035(2) -0.0013(18) 0.0014(18) -0.0023(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.424(3) . ? S1 O2 1.433(3) . ? S1 N1 1.600(3) . ? S1 C1 1.759(2) . ? N1 C8 1.477(5) . ? N1 C11 1.497(5) . ? N2 C15 1.462(5) . ? N2 C9 1.466(5) . ? N2 C10 1.467(5) . ? C1 C2 1.39 . ? C1 C6 1.39 . ? C2 C3 1.39 . ? C2 H2 0.93 . ? C3 C4 1.39 . ? C3 H3 0.93 . ? C4 C5 1.39 . ? C4 C7 1.514(5) . ? C5 C6 1.39 . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C8 C9 1.507(6) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 C11 1.510(5) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.532(5) . ? C11 H11 0.98 . ? C12 C14 1.514(6) . ? C12 C13 1.523(6) . ? C12 H12 0.98 . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C15 C16 1.515(4) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 C17 1.39 . ? C16 C21 1.39 . ? C17 C18 1.39 . ? C17 H17 0.93 . ? C18 C19 1.39 . ? C18 H18 0.93 . ? C19 C20 1.39 . ? C19 H19 0.93 . ? C20 C21 1.39 . ? C20 H20 0.93 . ? C21 H21 0.93 . ? 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 120.18(19) . . ? O1 S1 N1 106.53(18) . . ? O2 S1 N1 107.01(17) . . ? O1 S1 C1 106.76(16) . . ? O2 S1 C1 106.75(17) . . ? N1 S1 C1 109.32(17) . . ? C8 N1 C11 114.7(3) . . ? C8 N1 S1 121.9(3) . . ? C11 N1 S1 121.7(2) . . ? C15 N2 C9 111.5(3) . . ? C15 N2 C10 111.6(3) . . ? C9 N2 C10 108.0(3) . . ? C2 C1 C6 120 . . ? C2 C1 S1 120.03(15) . . ? C6 C1 S1 119.96(15) . . ? C1 C2 C3 120 . . ? C1 C2 H2 120 . . ? C3 C2 H2 120 . . ? C4 C3 C2 120 . . ? C4 C3 H3 120 . . ? C2 C3 H3 120 . . ? C3 C4 C5 120 . . ? C3 C4 C7 119.1(3) . . ? C5 C4 C7 120.8(3) . . ? C6 C5 C4 120 . . ? C6 C5 H5 120 . . ? C4 C5 H5 120 . . ? C5 C6 C1 120 . . ? C5 C6 H6 120 . . ? C1 C6 H6 120 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 111.9(3) . . ? N1 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? N1 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? N2 C9 C8 110.3(3) . . ? N2 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 . . ? N2 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? N2 C10 C11 110.8(3) . . ? N2 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N1 C11 C10 108.7(3) . . ? N1 C11 C12 109.6(3) . . ? C10 C11 C12 113.9(3) . . ? N1 C11 H11 108.2 . . ? C10 C11 H11 108.2 . . ? C12 C11 H11 108.2 . . ? C14 C12 C13 109.5(4) . . ? C14 C12 C11 111.7(3) . . ? C13 C12 C11 111.1(3) . . ? C14 C12 H12 108.2 . . ? C13 C12 H12 108.2 . . ? C11 C12 H12 108.2 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 112.6(3) . . ? N2 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? N2 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C17 C16 C21 120 . . ? C17 C16 C15 119.4(2) . . ? C21 C16 C15 120.5(2) . . ? C16 C17 C18 120 . . ? C16 C17 H17 120 . . ? C18 C17 H17 120 . . ? C19 C18 C17 120 . . ? C19 C18 H18 120 . . ? C17 C18 H18 120 . . ? C18 C19 C20 120 . . ? C18 C19 H19 120 . . ? C20 C19 H19 120 . . ? C19 C20 C21 120 . . ? C19 C20 H20 120 . . ? C21 C20 H20 120 . . ? C20 C21 C16 120 . . ? C20 C21 H21 120 . . ? C16 C21 H21 120 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C9 H9A O2 0.97 2.54 3.488(5) 165.1 1_655