# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Tohru Fukuyama' 'Mui Cheung' 'Fu She Han' 'Hiroyuki Osajima' 'Hidetoshi Tokuyama' _publ_contact_author_name 'Tohru Fukuyama' _publ_contact_author_address ; Graduate School of Pharmaceutical Sciences University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033 JAPAN ; _publ_contact_author_email FUKUYAMA@MOL.F.U-TOKYO.AC.JP _publ_requested_journal 'Chemical Communications' _publ_section_title ; Facile Synthesis of Chiral Cyclic Oligothiazolines: A Novel Structural Motif of Macrocyclic Molecule ; data_han1 _database_code_depnum_ccdc_archive 'CCDC 290621' _audit_creation_date 2003-12-17T14:38:30-00:00 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H42 Cl6 N8 S8' _chemical_formula_sum 'C34 H42 Cl6 N8 S8' _chemical_formula_weight 1031.99 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.8700(4) _cell_length_b 12.0090(9) _cell_length_c 12.7440(9) _cell_angle_alpha 116.294(3) _cell_angle_beta 88.966(5) _cell_angle_gamma 101.443(5) _cell_volume 1189.07(13) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 9419 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.73 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.748 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_unetI/netI 0.0185 _diffrn_reflns_number 3918 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.73 _diffrn_reflns_theta_full 25.73 _diffrn_measured_fraction_theta_full 0.862 _diffrn_measured_fraction_theta_max 0.862 _reflns_number_total 3918 _reflns_number_gt 3879 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection Xpress(MacScience) _computing_cell_refinement Scalepack(HKL) _computing_data_reduction 'Denzo and Scalepack(HKL)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.1045P)^2^+0.4389P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.132(8) _refine_ls_number_reflns 3918 _refine_ls_number_parameters 578 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1257 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.11(8) _refine_diff_density_max 0.913 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.079 #----------------------------------------------------------------------------# # 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 N1 N -0.4472(6) 0.4421(4) 1.0974(4) 0.0356(9) Uani 1 1 d . . . N2 N -0.4816(6) 0.1941(4) 0.9462(4) 0.0357(9) Uani 1 1 d . . . N3 N -0.0958(5) 0.2266(4) 0.8477(4) 0.0337(8) Uani 1 1 d . . . N4 N 0.1755(5) 0.2082(4) 0.6474(4) 0.0364(9) Uani 1 1 d . . . N5 N 0.2166(6) 0.5057(4) 0.6393(4) 0.0377(9) Uani 1 1 d . . . N6 N 0.1609(5) 0.7416(4) 0.7405(4) 0.0339(8) Uani 1 1 d . . . N7 N 0.0069(6) 0.7563(4) 1.0099(4) 0.0356(9) Uani 1 1 d . . . N8 N -0.2668(6) 0.7724(4) 1.2099(4) 0.0379(9) Uani 1 1 d . . . S1 S -0.57044(18) 0.42351(13) 1.27905(12) 0.0457(3) Uani 1 1 d . . . S2 S -0.21973(17) 0.21098(13) 1.04957(12) 0.0429(3) Uani 1 1 d . . . S3 S -0.15014(18) 0.05253(14) 0.62908(11) 0.0472(4) Uani 1 1 d . . . S4 S 0.24378(17) 0.43533(11) 0.82763(11) 0.0432(3) Uani 1 1 d . . . S5 S 0.5097(2) 0.55730(14) 0.6108(2) 0.0646(5) Uani 1 1 d . . . S6 S 0.30661(15) 0.78710(11) 0.93705(10) 0.0383(3) Uani 1 1 d . . . S7 S -0.2142(2) 0.87711(16) 1.02635(15) 0.0539(4) Uani 1 1 d . . . S8 S -0.13620(17) 0.57882(13) 1.15885(12) 0.0426(3) Uani 1 1 d . . . Cl1 Cl -0.1947(2) 0.44461(16) 0.44076(17) 0.0648(5) Uani 1 1 d . . . Cl2 Cl -0.0949(2) 0.71503(16) 0.51489(14) 0.0581(4) Uani 1 1 d . . . Cl3 Cl 0.0945(2) 0.53938(18) 0.37288(14) 0.0573(4) Uani 1 1 d . . . Cl4 Cl -0.5869(4) 0.9383(3) 0.44489(18) 0.0910(8) Uani 1 1 d . . . Cl5 Cl -0.6011(2) 0.97087(18) 0.23616(15) 0.0637(5) Uani 1 1 d . . . Cl6 Cl -0.3625(3) 1.13770(16) 0.42003(18) 0.0710(5) Uani 1 1 d . . . C1 C -0.5043(6) 0.3632(5) 1.1354(4) 0.0345(10) Uani 1 1 d . . . C2 C -0.4490(6) 0.5747(4) 1.1809(4) 0.0356(10) Uani 1 1 d . . . C3 C -0.4759(7) 0.5817(5) 1.3043(5) 0.0434(12) Uani 1 1 d . . . C4 C -0.5792(7) 0.6144(5) 1.1358(5) 0.0446(12) Uani 1 1 d . . . H4A H -0.6765 0.5615 1.1343 0.067 Uiso 1 1 calc R . . H4B H -0.5617 0.6048 1.058 0.067 Uiso 1 1 calc R . . H4C H -0.5805 0.7016 1.187 0.067 Uiso 1 1 calc R . . C5 C -0.3362(6) 0.2000(4) 0.9343(4) 0.0345(10) Uani 1 1 d . . . C6 C -0.5175(6) 0.2206(5) 1.0669(4) 0.0361(11) Uani 1 1 d . . . C7 C -0.3929(7) 0.1807(6) 1.1185(5) 0.0443(12) Uani 1 1 d . . . C8 C -0.6802(7) 0.1498(5) 1.0682(5) 0.0447(12) Uani 1 1 d . . . H8A H -0.6868 0.0599 1.0249 0.067 Uiso 1 1 calc R . . H8B H -0.7532 0.1746 1.0326 0.067 Uiso 1 1 calc R . . H8C H -0.7029 0.1703 1.1478 0.067 Uiso 1 1 calc R . . C9 C -0.0308(6) 0.1652(4) 0.7560(4) 0.0335(10) Uani 1 1 d . . . C10 C -0.2641(6) 0.1978(5) 0.8250(5) 0.0374(10) Uani 1 1 d . . . C11 C -0.3115(7) 0.0650(5) 0.7193(5) 0.0446(12) Uani 1 1 d . . . C12 C -0.3048(8) 0.3024(6) 0.8011(6) 0.0488(13) Uani 1 1 d . . . H12A H -0.2589 0.3008 0.7318 0.073 Uiso 1 1 calc R . . H12B H -0.2663 0.3835 0.8668 0.073 Uiso 1 1 calc R . . H12C H -0.4149 0.2887 0.7897 0.073 Uiso 1 1 calc R . . C13 C 0.2200(6) 0.3272(4) 0.6773(4) 0.0344(10) Uani 1 1 d . . . C14 C 0.1431(6) 0.1852(4) 0.7519(4) 0.0349(10) Uani 1 1 d . . . C15 C 0.2246(7) 0.3031(5) 0.8626(5) 0.0397(11) Uani 1 1 d . . . C16 C 0.1965(7) 0.0658(5) 0.7345(6) 0.0477(13) Uani 1 1 d . . . H16A H 0.3066 0.0796 0.7319 0.072 Uiso 1 1 calc R . . H16B H 0.1487 -0.0039 0.662 0.072 Uiso 1 1 calc R . . H16C H 0.1681 0.0463 0.7985 0.072 Uiso 1 1 calc R . . C17 C 0.3320(6) 0.5957(4) 0.6564(4) 0.0330(10) Uani 1 1 d . . . C18 C 0.2570(7) 0.3798(4) 0.5886(4) 0.0374(11) Uani 1 1 d . . . C19 C 0.4326(9) 0.3937(6) 0.5722(7) 0.0486(14) Uani 1 1 d . . . C20 C 0.1620(9) 0.2935(6) 0.4733(5) 0.0537(15) Uani 1 1 d . . . H20A H 0.1865 0.3278 0.4184 0.081 Uiso 1 1 calc R . . H20B H 0.0543 0.2876 0.486 0.081 Uiso 1 1 calc R . . H20C H 0.185 0.2105 0.4426 0.081 Uiso 1 1 calc R . . C21 C 0.1441(6) 0.7584(4) 0.8445(4) 0.0332(10) Uani 1 1 d . . . C22 C 0.3216(6) 0.7346(4) 0.7105(4) 0.0344(10) Uani 1 1 d . . . C23 C 0.4247(7) 0.8080(5) 0.8274(5) 0.0397(11) Uani 1 1 d . . . C24 C 0.3719(7) 0.7903(5) 0.6261(5) 0.0406(11) Uani 1 1 d . . . H24A H 0.3647 0.878 0.6611 0.061 Uiso 1 1 calc R . . H24B H 0.3061 0.7441 0.5545 0.061 Uiso 1 1 calc R . . H24C H 0.4766 0.784 0.6092 0.061 Uiso 1 1 calc R . . C25 C -0.0883(6) 0.8113(4) 1.0791(4) 0.0354(10) Uani 1 1 d . . . C26 C -0.0148(6) 0.7486(5) 0.8930(4) 0.0361(10) Uani 1 1 d . . . C27 C -0.0906(8) 0.8581(6) 0.9061(6) 0.0480(13) Uani 1 1 d . . . C28 C -0.1150(8) 0.6177(6) 0.8163(5) 0.0535(16) Uani 1 1 d . . . H28A H -0.2147 0.6111 0.8463 0.08 Uiso 1 1 calc R . . H28B H -0.0668 0.5532 0.8171 0.08 Uiso 1 1 calc R . . H28C H -0.1264 0.6065 0.7372 0.08 Uiso 1 1 calc R . . C29 C -0.2927(6) 0.6547(5) 1.1850(4) 0.0350(10) Uani 1 1 d . . . C30 C -0.1008(7) 0.8205(5) 1.2017(4) 0.0388(11) Uani 1 1 d . . . C31 C -0.0077(8) 0.7341(6) 1.2184(5) 0.0436(12) Uani 1 1 d . . . C32 C -0.0472(8) 0.9581(6) 1.2935(6) 0.0539(16) Uani 1 1 d . . . H32A H -0.0548 0.963 1.3706 0.081 Uiso 1 1 calc R . . H32B H -0.111 1.0092 1.2836 0.081 Uiso 1 1 calc R . . H32C H 0.0581 0.9888 1.284 0.081 Uiso 1 1 calc R . . C33 C -0.0345(7) 0.5719(6) 0.4834(5) 0.0466(12) Uani 1 1 d . . . C34 C -0.4784(9) 0.9834(6) 0.3482(5) 0.0502(13) Uani 1 1 d . . . H3A H -0.375(8) 0.615(6) 1.363(6) 0.036(15) Uiso 1 1 d . . . H3B H -0.532(6) 0.641(5) 1.350(4) 0.013(10) Uiso 1 1 d . . . H7A H -0.375(7) 0.219(5) 1.207(5) 0.031(14) Uiso 1 1 d . . . H7B H -0.427(10) 0.069(7) 1.077(7) 0.06(2) Uiso 1 1 d . . . H11A H -0.322(10) -0.022(7) 0.739(7) 0.06(2) Uiso 1 1 d . . . H11B H -0.421(9) 0.054(7) 0.673(6) 0.049(18) Uiso 1 1 d . . . H15A H 0.329(9) 0.287(6) 0.880(6) 0.039(15) Uiso 1 1 d . . . H15B H 0.171(6) 0.321(4) 0.938(4) 0.016(10) Uiso 1 1 d . . . H19A H 0.453(14) 0.371(11) 0.520(11) 0.08(4) Uiso 1 1 d . . . H19B H 0.487(15) 0.375(11) 0.625(10) 0.09(3) Uiso 1 1 d . . . H23A H 0.478(8) 0.907(6) 0.850(6) 0.040(16) Uiso 1 1 d . . . H23B H 0.507(13) 0.781(10) 0.824(9) 0.08(3) Uiso 1 1 d . . . H27A H -0.014(7) 0.931(5) 0.930(4) 0.018(11) Uiso 1 1 d . . . H27B H -0.147(11) 0.835(7) 0.838(8) 0.06(2) Uiso 1 1 d . . . H31A H 0.079(8) 0.741(5) 1.192(5) 0.024(13) Uiso 1 1 d . . . H31B H 0.022(9) 0.771(7) 1.310(6) 0.049(19) Uiso 1 1 d . . . H33 H 0.026(8) 0.576(6) 0.557(6) 0.040(16) Uiso 1 1 d . . . H34 H -0.403(7) 0.924(5) 0.302(5) 0.026(12) Uiso 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 N1 0.041(3) 0.0305(19) 0.036(2) 0.0146(16) 0.0061(16) 0.0097(16) N2 0.041(3) 0.0328(19) 0.036(2) 0.0171(16) 0.0097(17) 0.0098(16) N3 0.027(2) 0.0328(19) 0.042(2) 0.0184(16) 0.0055(16) 0.0040(14) N4 0.035(3) 0.0318(19) 0.042(2) 0.0166(17) 0.0131(17) 0.0079(16) N5 0.036(3) 0.0286(18) 0.050(2) 0.0190(17) 0.0075(17) 0.0076(16) N6 0.031(2) 0.0342(19) 0.038(2) 0.0173(16) 0.0077(16) 0.0098(15) N7 0.040(3) 0.0342(19) 0.035(2) 0.0168(16) 0.0088(16) 0.0093(16) N8 0.041(3) 0.033(2) 0.035(2) 0.0119(16) 0.0115(17) 0.0064(17) S1 0.0514(9) 0.0429(7) 0.0419(7) 0.0198(5) 0.0169(6) 0.0074(5) S2 0.0389(8) 0.0537(7) 0.0474(7) 0.0301(6) 0.0079(5) 0.0164(5) S3 0.0413(8) 0.0532(7) 0.0350(6) 0.0110(5) 0.0046(5) 0.0055(6) S4 0.0551(9) 0.0307(6) 0.0400(6) 0.0144(5) -0.0003(5) 0.0043(5) S5 0.0392(10) 0.0378(7) 0.1044(14) 0.0208(7) 0.0282(8) 0.0101(6) S6 0.0407(8) 0.0362(6) 0.0334(6) 0.0124(5) 0.0017(5) 0.0057(5) S7 0.0535(10) 0.0688(9) 0.0634(9) 0.0428(8) 0.0267(7) 0.0348(7) S8 0.0408(8) 0.0445(7) 0.0492(7) 0.0259(5) 0.0072(5) 0.0119(5) Cl1 0.0438(10) 0.0559(9) 0.0754(11) 0.0149(7) 0.0078(7) 0.0050(6) Cl2 0.0576(10) 0.0604(8) 0.0571(8) 0.0237(7) 0.0004(7) 0.0205(7) Cl3 0.0483(10) 0.0824(11) 0.0509(8) 0.0348(7) 0.0127(6) 0.0237(7) Cl4 0.119(2) 0.1104(17) 0.0529(10) 0.0495(11) 0.0154(10) 0.0131(14) Cl5 0.0685(12) 0.0725(10) 0.0573(9) 0.0418(8) -0.0088(7) -0.0021(8) Cl6 0.0726(13) 0.0430(7) 0.0787(11) 0.0081(7) -0.0140(9) 0.0170(7) C1 0.036(3) 0.033(2) 0.038(2) 0.0192(19) 0.0044(18) 0.0053(18) C2 0.041(3) 0.032(2) 0.034(2) 0.0153(18) 0.0054(19) 0.0082(19) C3 0.047(4) 0.044(3) 0.036(3) 0.017(2) 0.010(2) 0.006(2) C4 0.040(3) 0.035(2) 0.057(3) 0.018(2) -0.001(2) 0.008(2) C5 0.033(3) 0.031(2) 0.043(2) 0.0183(19) 0.0088(19) 0.0099(17) C6 0.039(3) 0.036(2) 0.041(2) 0.022(2) 0.013(2) 0.012(2) C7 0.046(4) 0.053(3) 0.050(3) 0.034(3) 0.017(2) 0.022(2) C8 0.046(3) 0.034(2) 0.054(3) 0.020(2) 0.013(2) 0.005(2) C9 0.034(3) 0.033(2) 0.037(2) 0.0182(18) 0.0065(18) 0.0086(18) C10 0.033(3) 0.036(2) 0.045(3) 0.021(2) 0.005(2) 0.0064(19) C11 0.035(3) 0.045(3) 0.043(3) 0.014(2) 0.001(2) 0.000(2) C12 0.046(4) 0.055(3) 0.065(4) 0.041(3) 0.018(3) 0.020(3) C13 0.035(3) 0.029(2) 0.041(2) 0.0175(18) 0.0073(19) 0.0070(17) C14 0.037(3) 0.031(2) 0.038(2) 0.0167(18) 0.0081(19) 0.0069(18) C15 0.040(3) 0.037(2) 0.041(3) 0.018(2) -0.002(2) 0.005(2) C16 0.039(3) 0.040(3) 0.074(4) 0.032(3) 0.010(3) 0.014(2) C17 0.038(3) 0.027(2) 0.029(2) 0.0090(16) 0.0072(18) 0.0065(17) C18 0.042(3) 0.032(2) 0.041(3) 0.018(2) 0.010(2) 0.0117(19) C19 0.050(4) 0.041(3) 0.063(4) 0.028(3) 0.022(3) 0.017(2) C20 0.077(5) 0.038(3) 0.041(3) 0.016(2) 0.005(3) 0.004(3) C21 0.040(3) 0.0268(19) 0.033(2) 0.0129(17) 0.0084(19) 0.0097(18) C22 0.030(3) 0.031(2) 0.040(2) 0.0148(18) 0.0056(18) 0.0065(18) C23 0.033(3) 0.036(2) 0.039(2) 0.0099(19) 0.001(2) 0.000(2) C24 0.042(3) 0.039(2) 0.046(3) 0.024(2) 0.014(2) 0.010(2) C25 0.038(3) 0.028(2) 0.039(2) 0.0131(18) 0.0098(19) 0.0081(18) C26 0.035(3) 0.038(2) 0.036(2) 0.0173(19) 0.0072(18) 0.0066(19) C27 0.052(4) 0.057(3) 0.051(3) 0.034(3) 0.017(3) 0.025(3) C28 0.049(4) 0.053(3) 0.042(3) 0.014(2) 0.010(2) -0.008(3) C29 0.040(3) 0.034(2) 0.031(2) 0.0159(18) 0.0051(18) 0.0043(19) C30 0.035(3) 0.041(2) 0.035(2) 0.013(2) 0.0124(19) 0.007(2) C31 0.035(3) 0.056(3) 0.044(3) 0.028(2) 0.004(2) 0.007(2) C32 0.052(4) 0.044(3) 0.048(3) 0.010(2) 0.018(3) -0.003(2) C33 0.040(3) 0.055(3) 0.045(3) 0.022(2) 0.009(2) 0.011(2) C34 0.060(4) 0.049(3) 0.045(3) 0.021(2) 0.006(2) 0.018(3) #----------------------------------------------------------------------------# # 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 N1 C1 1.264(7) . ? N1 C2 1.476(6) . ? N2 C5 1.287(8) . ? N2 C6 1.469(6) . ? N3 C9 1.274(7) . ? N3 C10 1.467(7) . ? N4 C13 1.282(6) . ? N4 C14 1.488(6) . ? N5 C17 1.274(7) . ? N5 C18 1.474(6) . ? N6 C21 1.260(7) . ? N6 C22 1.478(7) . ? N7 C25 1.267(7) . ? N7 C26 1.465(6) . ? N8 C29 1.276(7) . ? N8 C30 1.491(7) . ? S1 C1 1.782(5) . ? S1 C3 1.804(6) . ? S2 C5 1.753(5) . ? S2 C7 1.810(6) . ? S3 C9 1.767(5) . ? S3 C11 1.807(6) . ? S4 C13 1.761(5) . ? S4 C15 1.808(5) . ? S5 C17 1.747(5) . ? S5 C19 1.787(6) . ? S6 C21 1.758(5) . ? S6 C23 1.808(6) . ? S7 C25 1.781(5) . ? S7 C27 1.825(6) . ? S8 C29 1.756(6) . ? S8 C31 1.813(6) . ? Cl1 C33 1.755(7) . ? Cl2 C33 1.775(7) . ? Cl3 C33 1.754(6) . ? Cl4 C34 1.756(7) . ? Cl5 C34 1.745(7) . ? Cl6 C34 1.761(7) . ? C1 C6 1.520(7) . ? C2 C29 1.509(7) . ? C2 C4 1.542(8) . ? C2 C3 1.553(7) . ? C5 C10 1.513(7) . ? C6 C8 1.526(8) . ? C6 C7 1.549(7) . ? C9 C14 1.516(8) . ? C10 C12 1.524(7) . ? C10 C11 1.545(7) . ? C13 C18 1.524(7) . ? C14 C16 1.521(7) . ? C14 C15 1.542(7) . ? C17 C22 1.518(6) . ? C18 C20 1.513(8) . ? C18 C19 1.554(9) . ? C21 C26 1.533(7) . ? C22 C24 1.519(7) . ? C22 C23 1.548(7) . ? C25 C30 1.520(7) . ? C26 C28 1.527(7) . ? C26 C27 1.536(8) . ? C30 C32 1.524(7) . ? C30 C31 1.530(8) . ? 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 C1 N1 C2 113.1(4) . . ? C5 N2 C6 111.4(4) . . ? C9 N3 C10 111.8(4) . . ? C13 N4 C14 111.2(4) . . ? C17 N5 C18 113.0(5) . . ? C21 N6 C22 111.3(4) . . ? C25 N7 C26 112.5(5) . . ? C29 N8 C30 110.7(5) . . ? C1 S1 C3 89.2(2) . . ? C5 S2 C7 88.8(3) . . ? C9 S3 C11 88.5(2) . . ? C13 S4 C15 89.2(2) . . ? C17 S5 C19 91.0(3) . . ? C21 S6 C23 87.7(3) . . ? C25 S7 C27 88.0(3) . . ? C29 S8 C31 88.5(3) . . ? N1 C1 C6 123.9(5) . . ? N1 C1 S1 117.9(4) . . ? C6 C1 S1 118.2(3) . . ? N1 C2 C29 107.4(4) . . ? N1 C2 C4 107.7(4) . . ? C29 C2 C4 111.9(4) . . ? N1 C2 C3 108.7(4) . . ? C29 C2 C3 109.4(4) . . ? C4 C2 C3 111.7(5) . . ? C2 C3 S1 106.0(4) . . ? N2 C5 C10 122.3(5) . . ? N2 C5 S2 118.1(4) . . ? C10 C5 S2 119.6(4) . . ? N2 C6 C1 107.2(4) . . ? N2 C6 C8 110.6(5) . . ? C1 C6 C8 110.3(4) . . ? N2 C6 C7 107.1(4) . . ? C1 C6 C7 109.3(5) . . ? C8 C6 C7 112.2(4) . . ? C6 C7 S2 104.9(3) . . ? N3 C9 C14 122.8(5) . . ? N3 C9 S3 117.9(4) . . ? C14 C9 S3 119.3(4) . . ? N3 C10 C5 108.1(4) . . ? N3 C10 C12 107.2(4) . . ? C5 C10 C12 109.7(4) . . ? N3 C10 C11 107.8(4) . . ? C5 C10 C11 111.2(4) . . ? C12 C10 C11 112.6(5) . . ? C10 C11 S3 104.5(4) . . ? N4 C13 C18 123.0(4) . . ? N4 C13 S4 118.9(4) . . ? C18 C13 S4 118.2(3) . . ? N4 C14 C9 105.2(4) . . ? N4 C14 C16 109.1(4) . . ? C9 C14 C16 110.3(4) . . ? N4 C14 C15 109.0(4) . . ? C9 C14 C15 110.9(4) . . ? C16 C14 C15 112.1(5) . . ? C14 C15 S4 105.7(3) . . ? N5 C17 C22 123.3(5) . . ? N5 C17 S5 118.5(4) . . ? C22 C17 S5 118.2(4) . . ? N5 C18 C20 109.8(5) . . ? N5 C18 C13 106.6(4) . . ? C20 C18 C13 110.4(4) . . ? N5 C18 C19 110.1(4) . . ? C20 C18 C19 111.3(6) . . ? C13 C18 C19 108.6(5) . . ? C18 C19 S5 107.1(4) . . ? N6 C21 C26 122.5(5) . . ? N6 C21 S6 119.6(4) . . ? C26 C21 S6 117.9(3) . . ? N6 C22 C17 107.7(4) . . ? N6 C22 C24 112.3(4) . . ? C17 C22 C24 110.2(4) . . ? N6 C22 C23 106.8(4) . . ? C17 C22 C23 109.0(4) . . ? C24 C22 C23 110.7(4) . . ? C22 C23 S6 105.4(4) . . ? N7 C25 C30 123.1(5) . . ? N7 C25 S7 117.2(4) . . ? C30 C25 S7 119.7(4) . . ? N7 C26 C28 106.8(4) . . ? N7 C26 C21 107.8(4) . . ? C28 C26 C21 109.1(4) . . ? N7 C26 C27 107.8(4) . . ? C28 C26 C27 113.0(6) . . ? C21 C26 C27 112.1(4) . . ? C26 C27 S7 104.0(4) . . ? N8 C29 C2 124.9(5) . . ? N8 C29 S8 118.8(4) . . ? C2 C29 S8 116.3(4) . . ? N8 C30 C25 106.3(4) . . ? N8 C30 C32 110.7(4) . . ? C25 C30 C32 110.0(5) . . ? N8 C30 C31 108.0(4) . . ? C25 C30 C31 110.5(4) . . ? C32 C30 C31 111.2(5) . . ? C30 C31 S8 104.9(4) . . ? Cl3 C33 Cl1 109.9(3) . . ? Cl3 C33 Cl2 111.0(3) . . ? Cl1 C33 Cl2 110.3(4) . . ? Cl5 C34 Cl4 109.8(4) . . ? Cl5 C34 Cl6 110.7(3) . . ? Cl4 C34 Cl6 112.6(3) . . ?