# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 177 _publ_requested_journal 'Organic & Biomolecular Chemistry' loop_ _publ_author_name 'Vicente, J.' 'Chicote, M. T.' _publ_contact_author_name J.Vicente, _publ_contact_author_address ; Facultad de Quimica Universidad de Murcia Murcia, Aptdo. Spain 4021, E-30071 ; _publ_contact_author_email jvs1@um.es # Attachment '3a2.cif' data_ajf49rbs _database_code_depnum_ccdc_archive 'CCDC 800053' #TrackingRef '3a2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 Cl3 F3 N2 O3 S' _chemical_formula_weight 595.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.8646(11) _cell_length_b 12.0601(11) _cell_length_c 20.4915(18) _cell_angle_alpha 90.00 _cell_angle_beta 94.238(2) _cell_angle_gamma 90.00 _cell_volume 2677.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5996 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 25.53 _exptl_crystal_description lath _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.472 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8680 _exptl_absorpt_correction_T_max 0.9722 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32587 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.73 _reflns_number_total 6510 _reflns_number_gt 5168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+1.9022P] 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 'NH free with DFIX, rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6510 _refine_ls_number_parameters 341 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.1024 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.04774(18) 0.38175(16) 0.21850(9) 0.0154(4) Uani 1 1 d . . . H1 H -0.0728 0.3160 0.1957 0.018 Uiso 1 1 calc R . . N1 N 0.05992(15) 0.42423(13) 0.20876(8) 0.0148(3) Uani 1 1 d . . . C2 C -0.12867(18) 0.42972(16) 0.26162(9) 0.0161(4) Uani 1 1 d . . . C3 C -0.08059(18) 0.51543(17) 0.30287(9) 0.0163(4) Uani 1 1 d . . . C4 C -0.1528(2) 0.55665(18) 0.35128(10) 0.0207(4) Uani 1 1 d . . . H4 H -0.1218 0.6135 0.3801 0.025 Uiso 1 1 calc R . . C5 C -0.2684(2) 0.51411(19) 0.35664(11) 0.0250(5) Uani 1 1 d . . . H5 H -0.3173 0.5433 0.3892 0.030 Uiso 1 1 calc R . . C6 C -0.3172(2) 0.42935(19) 0.31605(11) 0.0249(5) Uani 1 1 d . . . H6 H -0.3978 0.4017 0.3211 0.030 Uiso 1 1 calc R . . C7 C -0.24761(19) 0.38646(18) 0.26890(10) 0.0203(4) Uani 1 1 d . . . H7 H -0.2792 0.3281 0.2414 0.024 Uiso 1 1 calc R . . C8 C 0.09621(18) 0.53657(16) 0.23625(9) 0.0155(4) Uani 1 1 d . . . H8 H 0.1874 0.5360 0.2475 0.019 Uiso 1 1 calc R . . N2 N 0.03630(17) 0.55123(15) 0.29608(8) 0.0178(4) Uani 1 1 d . . . H02 H 0.073(2) 0.590(2) 0.3234(12) 0.017(6) Uiso 1 1 d . . . C11 C 0.06887(18) 0.62398(16) 0.18421(9) 0.0156(4) Uani 1 1 d . . . C12 C -0.04332(19) 0.67958(17) 0.17661(10) 0.0174(4) Uani 1 1 d . . . H12 H -0.1056 0.6652 0.2057 0.021 Uiso 1 1 calc R . . C13 C -0.0644(2) 0.75642(17) 0.12624(10) 0.0194(4) Uani 1 1 d . . . H13 H -0.1416 0.7935 0.1212 0.023 Uiso 1 1 calc R . . C14 C 0.0253(2) 0.77980(17) 0.08334(10) 0.0188(4) Uani 1 1 d . . . C15 C 0.1372(2) 0.72392(18) 0.09158(10) 0.0216(4) Uani 1 1 d . . . H15 H 0.1997 0.7387 0.0627 0.026 Uiso 1 1 calc R . . C16 C 0.15907(19) 0.64712(17) 0.14125(10) 0.0205(4) Uani 1 1 d . . . H16 H 0.2362 0.6099 0.1461 0.025 Uiso 1 1 calc R . . C17 C 0.0032(2) 0.86501(18) 0.02994(11) 0.0253(5) Uani 1 1 d . . . H17A H 0.0430 0.9349 0.0438 0.038 Uiso 1 1 calc R . . H17B H -0.0857 0.8770 0.0213 0.038 Uiso 1 1 calc R . . H17C H 0.0381 0.8385 -0.0100 0.038 Uiso 1 1 calc R . . C21 C 0.14201(19) 0.37655(16) 0.16354(10) 0.0167(4) Uani 1 1 d . . . C22 C 0.2586(2) 0.34098(17) 0.18764(11) 0.0205(4) Uani 1 1 d . . . C23 C 0.3385(2) 0.30284(18) 0.14258(12) 0.0258(5) Uani 1 1 d . . . H23 H 0.4182 0.2768 0.1575 0.031 Uiso 1 1 calc R . . C24 C 0.3034(2) 0.30238(19) 0.07657(12) 0.0297(5) Uani 1 1 d . . . H24 H 0.3599 0.2781 0.0464 0.036 Uiso 1 1 calc R . . C25 C 0.1863(2) 0.33701(18) 0.05386(11) 0.0259(5) Uani 1 1 d . . . H25 H 0.1633 0.3350 0.0082 0.031 Uiso 1 1 calc R . . C26 C 0.1018(2) 0.37475(17) 0.09672(10) 0.0196(4) Uani 1 1 d . . . C27 C -0.0242(2) 0.41377(18) 0.07092(10) 0.0230(5) Uani 1 1 d . . . H27A H -0.0290 0.4142 0.0230 0.034 Uiso 1 1 calc R . . H27B H -0.0385 0.4889 0.0870 0.034 Uiso 1 1 calc R . . H27C H -0.0871 0.3636 0.0860 0.034 Uiso 1 1 calc R . . C28 C 0.3007(2) 0.34262(19) 0.25951(11) 0.0239(5) Uani 1 1 d . . . H28A H 0.3550 0.4065 0.2687 0.036 Uiso 1 1 calc R . . H28B H 0.3457 0.2741 0.2710 0.036 Uiso 1 1 calc R . . H28C H 0.2287 0.3484 0.2854 0.036 Uiso 1 1 calc R . . C98 C 0.5353(2) 0.5401(2) 0.10997(11) 0.0242(5) Uani 1 1 d . . . H98 H 0.5248 0.4586 0.1025 0.029 Uiso 1 1 calc R . . Cl1 Cl 0.69168(5) 0.57386(6) 0.10566(3) 0.03931(17) Uani 1 1 d . . . Cl2 Cl 0.48861(5) 0.57242(5) 0.18854(3) 0.02830(14) Uani 1 1 d . . . Cl3 Cl 0.44369(6) 0.61155(6) 0.04920(3) 0.03491(16) Uani 1 1 d . . . C99 C 0.6413(2) 0.0762(2) 0.06184(12) 0.0326(6) Uani 1 1 d . . . F1 F 0.52032(15) 0.06098(17) 0.06014(8) 0.0607(6) Uani 1 1 d . . . F2 F 0.69563(19) -0.01954(13) 0.07810(10) 0.0618(5) Uani 1 1 d . . . F3 F 0.67030(15) 0.10136(15) 0.00180(7) 0.0489(5) Uani 1 1 d . . . S1 S 0.68924(5) 0.18407(4) 0.11999(2) 0.01900(12) Uani 1 1 d . . . O1 O 0.65284(16) 0.14173(15) 0.18121(8) 0.0314(4) Uani 1 1 d . . . O2 O 0.82191(13) 0.18870(13) 0.11572(8) 0.0245(3) Uani 1 1 d . . . O3 O 0.62501(15) 0.28044(14) 0.09517(8) 0.0332(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0191(10) 0.0123(9) 0.0143(9) 0.0034(7) -0.0012(7) 0.0002(8) N1 0.0177(8) 0.0120(8) 0.0148(8) 0.0005(6) 0.0018(6) -0.0001(7) C2 0.0190(10) 0.0158(10) 0.0137(9) 0.0029(7) 0.0020(7) 0.0029(8) C3 0.0197(10) 0.0164(10) 0.0127(9) 0.0048(7) 0.0000(8) 0.0022(8) C4 0.0286(12) 0.0174(10) 0.0166(10) 0.0009(8) 0.0041(8) 0.0036(9) C5 0.0296(12) 0.0248(11) 0.0218(11) 0.0036(9) 0.0110(9) 0.0088(9) C6 0.0190(10) 0.0283(12) 0.0281(11) 0.0065(9) 0.0065(9) 0.0023(9) C7 0.0204(10) 0.0209(10) 0.0194(10) 0.0015(8) 0.0007(8) -0.0019(9) C8 0.0163(9) 0.0143(9) 0.0159(9) -0.0012(7) 0.0002(7) -0.0022(8) N2 0.0223(9) 0.0181(9) 0.0129(8) -0.0030(7) 0.0005(7) -0.0029(7) C11 0.0205(10) 0.0112(9) 0.0149(9) -0.0026(7) 0.0004(8) -0.0017(8) C12 0.0198(10) 0.0173(10) 0.0155(9) -0.0021(8) 0.0042(8) -0.0011(8) C13 0.0217(10) 0.0169(10) 0.0193(10) -0.0009(8) -0.0009(8) 0.0030(8) C14 0.0271(11) 0.0127(9) 0.0162(9) -0.0011(8) -0.0014(8) -0.0027(8) C15 0.0224(11) 0.0216(11) 0.0215(10) 0.0024(8) 0.0057(8) -0.0040(9) C16 0.0171(10) 0.0184(10) 0.0261(11) 0.0016(8) 0.0019(8) -0.0007(8) C17 0.0333(12) 0.0216(11) 0.0207(11) 0.0045(9) -0.0012(9) -0.0026(9) C21 0.0198(10) 0.0119(9) 0.0196(10) -0.0008(8) 0.0083(8) -0.0021(8) C22 0.0225(11) 0.0129(10) 0.0269(11) 0.0031(8) 0.0067(9) -0.0032(8) C23 0.0204(11) 0.0185(11) 0.0396(13) 0.0003(9) 0.0100(10) -0.0011(9) C24 0.0343(13) 0.0223(12) 0.0351(13) -0.0060(10) 0.0213(11) -0.0049(10) C25 0.0361(13) 0.0221(11) 0.0208(11) -0.0047(9) 0.0116(9) -0.0084(10) C26 0.0272(11) 0.0145(10) 0.0178(10) 0.0008(8) 0.0067(8) -0.0054(8) C27 0.0293(12) 0.0235(11) 0.0161(10) 0.0007(8) 0.0015(8) -0.0058(9) C28 0.0198(10) 0.0245(11) 0.0275(12) 0.0073(9) 0.0017(9) 0.0029(9) C98 0.0190(11) 0.0285(12) 0.0251(11) 0.0027(9) 0.0021(9) -0.0011(9) Cl1 0.0196(3) 0.0563(4) 0.0425(4) 0.0055(3) 0.0057(2) -0.0052(3) Cl2 0.0256(3) 0.0363(3) 0.0230(3) 0.0030(2) 0.0020(2) -0.0043(2) Cl3 0.0320(3) 0.0477(4) 0.0248(3) 0.0053(3) 0.0008(2) 0.0136(3) C99 0.0296(13) 0.0385(15) 0.0312(13) -0.0155(11) 0.0122(10) -0.0142(11) F1 0.0332(9) 0.1010(15) 0.0500(10) -0.0405(10) 0.0169(7) -0.0365(9) F2 0.0842(14) 0.0254(9) 0.0785(14) -0.0178(9) 0.0251(11) -0.0065(9) F3 0.0454(9) 0.0786(12) 0.0242(8) -0.0215(8) 0.0124(7) -0.0227(9) S1 0.0192(3) 0.0200(3) 0.0175(2) -0.00160(19) -0.00021(19) 0.0002(2) O1 0.0365(10) 0.0396(10) 0.0184(8) 0.0007(7) 0.0042(7) -0.0046(8) O2 0.0190(8) 0.0243(8) 0.0294(8) 0.0058(6) -0.0034(6) -0.0016(6) O3 0.0301(9) 0.0308(9) 0.0385(10) 0.0043(8) 0.0006(7) 0.0115(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.306(3) . ? C1 C2 1.416(3) . ? N1 C21 1.451(2) . ? N1 C8 1.509(2) . ? C2 C3 1.411(3) . ? C2 C7 1.412(3) . ? C3 N2 1.358(3) . ? C3 C4 1.400(3) . ? C4 C5 1.369(3) . ? C5 C6 1.398(3) . ? C6 C7 1.371(3) . ? C8 N2 1.441(3) . ? C8 C11 1.513(3) . ? C11 C12 1.390(3) . ? C11 C16 1.393(3) . ? C12 C13 1.393(3) . ? C13 C14 1.388(3) . ? C14 C15 1.390(3) . ? C14 C17 1.507(3) . ? C15 C16 1.384(3) . ? C21 C22 1.393(3) . ? C21 C26 1.406(3) . ? C22 C23 1.391(3) . ? C22 C28 1.510(3) . ? C23 C24 1.378(3) . ? C24 C25 1.386(3) . ? C25 C26 1.393(3) . ? C26 C27 1.506(3) . ? C98 Cl1 1.756(2) . ? C98 Cl3 1.761(2) . ? C98 Cl2 1.767(2) . ? C99 F1 1.325(3) . ? C99 F3 1.327(3) . ? C99 F2 1.328(3) . ? C99 S1 1.814(2) . ? S1 O3 1.4297(17) . ? S1 O1 1.4368(16) . ? S1 O2 1.4516(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.67(18) . . ? C1 N1 C21 122.80(17) . . ? C1 N1 C8 120.51(16) . . ? C21 N1 C8 115.99(15) . . ? C3 C2 C7 120.58(18) . . ? C3 C2 C1 116.99(18) . . ? C7 C2 C1 122.05(19) . . ? N2 C3 C4 122.44(19) . . ? N2 C3 C2 118.63(18) . . ? C4 C3 C2 118.85(19) . . ? C5 C4 C3 119.3(2) . . ? C4 C5 C6 122.4(2) . . ? C7 C6 C5 119.4(2) . . ? C6 C7 C2 119.4(2) . . ? N2 C8 N1 107.81(15) . . ? N2 C8 C11 115.89(17) . . ? N1 C8 C11 109.28(15) . . ? C3 N2 C8 122.20(17) . . ? C12 C11 C16 118.99(18) . . ? C12 C11 C8 122.68(18) . . ? C16 C11 C8 118.31(18) . . ? C11 C12 C13 119.91(19) . . ? C14 C13 C12 121.30(19) . . ? C13 C14 C15 118.24(19) . . ? C13 C14 C17 121.13(19) . . ? C15 C14 C17 120.62(19) . . ? C16 C15 C14 121.01(19) . . ? C15 C16 C11 120.55(19) . . ? C22 C21 C26 123.32(19) . . ? C22 C21 N1 118.78(18) . . ? C26 C21 N1 117.79(18) . . ? C23 C22 C21 117.5(2) . . ? C23 C22 C28 119.5(2) . . ? C21 C22 C28 122.93(19) . . ? C24 C23 C22 120.8(2) . . ? C23 C24 C25 120.6(2) . . ? C24 C25 C26 121.2(2) . . ? C25 C26 C21 116.5(2) . . ? C25 C26 C27 120.3(2) . . ? C21 C26 C27 123.09(18) . . ? Cl1 C98 Cl3 110.45(12) . . ? Cl1 C98 Cl2 109.79(12) . . ? Cl3 C98 Cl2 110.52(12) . . ? F1 C99 F3 108.1(2) . . ? F1 C99 F2 107.9(2) . . ? F3 C99 F2 107.4(2) . . ? F1 C99 S1 110.66(16) . . ? F3 C99 S1 111.64(17) . . ? F2 C99 S1 110.98(19) . . ? O3 S1 O1 116.16(10) . . ? O3 S1 O2 114.08(10) . . ? O1 S1 O2 113.89(10) . . ? O3 S1 C99 103.91(12) . . ? O1 S1 C99 103.56(11) . . ? O2 S1 C99 103.07(10) . . ? 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 C98 H98 O3 1.00 2.42 3.300(3) 146.7 . N2 H02 O2 0.81(2) 2.01(3) 2.824(2) 174(2) 2_655 C8 H8 O1 1.00 2.53 3.350(3) 139.0 2_655 C1 H1 O2 0.95 2.46 3.379(3) 161.6 1_455 C27 H27C O2 0.98 2.43 3.351(3) 157.3 1_455 C5 H5 F1 0.95 2.52 3.378(3) 150.9 2 _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.513 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.070 # Attachment '3b3.cif' data_ajf53bsi _database_code_depnum_ccdc_archive 'CCDC 800054' #TrackingRef '3b3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H23 F3 N2 O3 S' _chemical_formula_weight 476.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P bca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.6246(14) _cell_length_b 12.9407(11) _cell_length_c 20.1134(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4587.4(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6472 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 22.78 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8769 _exptl_absorpt_correction_T_max 0.9771 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54529 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.81 _reflns_number_total 5745 _reflns_number_gt 4168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The triflate anion is disordered over two positions, 50:42%, because of that same restrains are used to make it converge. Nevertherlesss, the highest peak of 1.30 e/A^3 is at 0.76 A from F2. ; _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^)+(0.0979P)^2^+9.4262P] 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 'NH free, rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5745 _refine_ls_number_parameters 297 _refine_ls_number_restraints 46 _refine_ls_R_factor_all 0.1136 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.2232 _refine_ls_wR_factor_gt 0.2030 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.46226(19) 0.4457(2) 0.30543(16) 0.0291(7) Uani 1 1 d . . . H1 H 0.5088 0.4797 0.3148 0.035 Uiso 1 1 calc R . . N1 N 0.44345(14) 0.42787(19) 0.24351(13) 0.0268(5) Uani 1 1 d . . . C2 C 0.41470(19) 0.4152(2) 0.35870(16) 0.0309(7) Uani 1 1 d . . . C3 C 0.3382(2) 0.3930(2) 0.34291(17) 0.0326(7) Uani 1 1 d . . . C4 C 0.2847(2) 0.3871(3) 0.39493(19) 0.0405(8) Uani 1 1 d . . . H4 H 0.2328 0.3735 0.3855 0.049 Uiso 1 1 calc R . . C5 C 0.3085(2) 0.4011(3) 0.4593(2) 0.0460(9) Uani 1 1 d . . . H5 H 0.2721 0.3977 0.4941 0.055 Uiso 1 1 calc R . . C6 C 0.3845(3) 0.4202(3) 0.47551(18) 0.0446(9) Uani 1 1 d . . . H6 H 0.3995 0.4276 0.5206 0.053 Uiso 1 1 calc R . . C7 C 0.4368(2) 0.4282(3) 0.42577(17) 0.0376(8) Uani 1 1 d . . . H7 H 0.4883 0.4426 0.4362 0.045 Uiso 1 1 calc R . . C8 C 0.37831(18) 0.3565(2) 0.23134(16) 0.0300(7) Uani 1 1 d . . . H8 H 0.3591 0.3669 0.1850 0.036 Uiso 1 1 calc R . . N2 N 0.31970(16) 0.3843(2) 0.27784(15) 0.0338(6) Uani 1 1 d . . . H02 H 0.273(2) 0.386(3) 0.264(2) 0.046(11) Uiso 1 1 d . . . C9 C 0.40451(18) 0.2427(2) 0.23969(17) 0.0319(7) Uani 1 1 d . . . H9 H 0.4162 0.2317 0.2878 0.038 Uiso 1 1 calc R . . C10 C 0.3379(2) 0.1720(3) 0.2218(2) 0.0454(9) Uani 1 1 d . . . H10A H 0.3241 0.1825 0.1750 0.068 Uiso 1 1 calc R . . H10B H 0.2944 0.1884 0.2501 0.068 Uiso 1 1 calc R . . H10C H 0.3527 0.0998 0.2286 0.068 Uiso 1 1 calc R . . C11 C 0.47632(18) 0.2213(2) 0.20096(16) 0.0301(7) Uani 1 1 d . . . C12 C 0.54474(19) 0.2096(2) 0.23428(17) 0.0302(7) Uani 1 1 d . . . H12 H 0.5457 0.2143 0.2814 0.036 Uiso 1 1 calc R . . C13 C 0.6117(2) 0.1912(3) 0.20002(19) 0.0387(8) Uani 1 1 d . . . H13 H 0.6580 0.1832 0.2236 0.046 Uiso 1 1 calc R . . C14 C 0.6109(2) 0.1847(3) 0.1313(2) 0.0423(9) Uani 1 1 d . . . H14 H 0.6564 0.1713 0.1076 0.051 Uiso 1 1 calc R . . C15 C 0.5431(2) 0.1978(3) 0.09733(18) 0.0426(9) Uani 1 1 d . . . H15 H 0.5426 0.1950 0.0501 0.051 Uiso 1 1 calc R . . C16 C 0.4765(2) 0.2148(3) 0.13162(17) 0.0366(8) Uani 1 1 d . . . H16 H 0.4302 0.2223 0.1078 0.044 Uiso 1 1 calc R . . C21 C 0.48442(18) 0.4725(2) 0.18797(15) 0.0276(6) Uani 1 1 d . . . C22 C 0.4442(2) 0.5165(3) 0.13598(16) 0.0333(7) Uani 1 1 d . . . H22 H 0.3904 0.5149 0.1353 0.040 Uiso 1 1 calc R . . C23 C 0.4848(2) 0.5630(3) 0.08475(17) 0.0396(8) Uani 1 1 d . . . H23 H 0.4577 0.5927 0.0486 0.048 Uiso 1 1 calc R . . C24 C 0.5635(2) 0.5674(3) 0.08477(18) 0.0394(8) Uani 1 1 d . . . C25 C 0.6013(2) 0.5214(3) 0.13754(19) 0.0397(8) Uani 1 1 d . . . H25 H 0.6552 0.5233 0.1385 0.048 Uiso 1 1 calc R . . C26 C 0.56289(19) 0.4728(2) 0.18895(18) 0.0334(7) Uani 1 1 d . . . H26 H 0.5899 0.4405 0.2241 0.040 Uiso 1 1 calc R . . C27 C 0.6063(3) 0.6210(3) 0.0295(2) 0.0567(11) Uani 1 1 d . . . H27A H 0.5728 0.6302 -0.0089 0.085 Uiso 1 1 calc R . . H27B H 0.6501 0.5789 0.0166 0.085 Uiso 1 1 calc R . . H27C H 0.6238 0.6887 0.0451 0.085 Uiso 1 1 calc R . . C99 C 0.2004(4) 0.3085(5) 0.0750(3) 0.0381(15) Uiso 0.580(7) 1 d PD A 1 F1 F 0.1952(3) 0.3471(4) 0.0133(2) 0.0521(14) Uiso 0.580(7) 1 d PD A 1 F2 F 0.1505(4) 0.2345(5) 0.0868(3) 0.084(2) Uiso 0.580(7) 1 d PD A 1 F3 F 0.2676(2) 0.2668(3) 0.0812(2) 0.0501(13) Uiso 0.580(7) 1 d PD A 1 S1 S 0.18695(12) 0.4087(2) 0.13415(10) 0.0244(6) Uiso 0.580(7) 1 d PD A 1 O1 O 0.1903(4) 0.3598(5) 0.1983(3) 0.0354(18) Uiso 0.580(7) 1 d PD A 1 O2 O 0.2580(4) 0.4583(6) 0.1174(4) 0.056(2) Uiso 0.580(7) 1 d PD A 1 O3 O 0.1135(3) 0.4497(5) 0.1184(3) 0.0460(14) Uiso 0.580(7) 1 d PD A 1 C99' C 0.1708(6) 0.3146(7) 0.0833(4) 0.048(3) Uiso 0.420(7) 1 d PD A 2 F1' F 0.1739(4) 0.3263(6) 0.0181(3) 0.054(2) Uiso 0.420(7) 1 d PD A 2 F2' F 0.1011(4) 0.2734(5) 0.0894(3) 0.070(2) Uiso 0.420(7) 1 d PD A 2 F3' F 0.2180(5) 0.2337(6) 0.0925(4) 0.081(3) Uiso 0.420(7) 1 d PD A 2 S1' S 0.18795(16) 0.4276(3) 0.13521(14) 0.0241(9) Uiso 0.420(7) 1 d PD A 2 O1' O 0.1860(5) 0.3816(7) 0.2015(4) 0.033(2) Uiso 0.420(7) 1 d PD A 2 O2' O 0.2504(4) 0.4853(6) 0.1189(3) 0.0301(17) Uiso 0.420(7) 1 d PD A 2 O3' O 0.1236(3) 0.4879(5) 0.1205(3) 0.0267(14) Uiso 0.420(7) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0325(16) 0.0229(14) 0.0319(16) 0.0007(12) -0.0068(13) 0.0025(12) N1 0.0288(13) 0.0212(12) 0.0304(13) 0.0004(10) -0.0042(10) 0.0010(10) C2 0.0345(17) 0.0251(15) 0.0330(16) 0.0015(12) -0.0017(13) 0.0047(13) C3 0.0353(17) 0.0250(15) 0.0375(18) 0.0009(13) -0.0026(14) 0.0085(13) C4 0.0380(18) 0.0318(17) 0.052(2) 0.0069(16) 0.0084(16) 0.0073(15) C5 0.062(3) 0.0337(19) 0.042(2) 0.0079(16) 0.0151(18) 0.0095(17) C6 0.070(3) 0.0321(18) 0.0316(18) 0.0069(14) 0.0019(17) 0.0046(18) C7 0.047(2) 0.0316(17) 0.0341(18) 0.0033(14) -0.0054(15) 0.0024(15) C8 0.0297(16) 0.0291(16) 0.0313(16) 0.0014(12) -0.0051(13) -0.0007(12) N2 0.0262(14) 0.0347(15) 0.0405(16) 0.0016(12) -0.0034(12) 0.0038(11) C9 0.0304(16) 0.0277(15) 0.0376(17) 0.0000(13) -0.0033(13) 0.0011(13) C10 0.0360(19) 0.0305(17) 0.070(3) -0.0022(17) -0.0044(18) -0.0004(15) C11 0.0336(17) 0.0222(14) 0.0345(17) -0.0009(12) -0.0047(13) -0.0018(12) C12 0.0360(17) 0.0229(14) 0.0315(16) -0.0002(12) -0.0042(13) -0.0006(12) C13 0.0332(18) 0.0324(17) 0.050(2) -0.0031(15) -0.0061(15) -0.0020(14) C14 0.045(2) 0.0343(18) 0.048(2) -0.0091(16) 0.0098(17) -0.0045(16) C15 0.061(2) 0.0369(19) 0.0297(17) -0.0055(14) 0.0038(16) -0.0028(17) C16 0.0427(19) 0.0305(17) 0.0366(18) -0.0030(14) -0.0099(15) 0.0000(14) C21 0.0339(16) 0.0195(13) 0.0294(15) -0.0026(12) 0.0001(12) -0.0002(12) C22 0.0396(18) 0.0312(16) 0.0290(16) -0.0018(13) -0.0020(14) 0.0033(14) C23 0.058(2) 0.0300(17) 0.0307(17) 0.0007(14) -0.0019(16) 0.0056(16) C24 0.054(2) 0.0258(17) 0.0385(19) -0.0049(14) 0.0112(16) -0.0031(15) C25 0.0380(19) 0.0285(17) 0.053(2) -0.0036(15) 0.0074(16) -0.0027(14) C26 0.0343(17) 0.0252(15) 0.0407(18) 0.0007(13) -0.0045(14) 0.0007(13) C27 0.080(3) 0.040(2) 0.050(2) 0.0010(18) 0.016(2) -0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.309(4) . ? C1 C2 1.416(5) . ? N1 C21 1.450(4) . ? N1 C8 1.494(4) . ? C2 C3 1.414(5) . ? C2 C7 1.414(5) . ? C3 N2 1.353(4) . ? C3 C4 1.411(5) . ? C4 C5 1.374(6) . ? C5 C6 1.400(6) . ? C6 C7 1.364(5) . ? C8 N2 1.439(4) . ? C8 C9 1.552(4) . ? C9 C11 1.512(5) . ? C9 C10 1.532(5) . ? C11 C12 1.388(4) . ? C11 C16 1.397(5) . ? C12 C13 1.387(5) . ? C13 C14 1.386(5) . ? C14 C15 1.385(6) . ? C15 C16 1.380(5) . ? C21 C26 1.383(5) . ? C21 C22 1.385(5) . ? C22 C23 1.391(5) . ? C23 C24 1.389(5) . ? C24 C25 1.387(5) . ? C24 C27 1.512(5) . ? C25 C26 1.387(5) . ? C99 F3 1.308(7) . ? C99 F2 1.321(7) . ? C99 F1 1.341(7) . ? C99 S1 1.777(7) . ? S1 O3 1.434(5) . ? S1 O1 1.438(6) . ? S1 O2 1.446(6) . ? C99' F1' 1.320(9) . ? C99' F2' 1.344(10) . ? C99' F3' 1.350(10) . ? C99' S1' 1.822(9) . ? S1' O2' 1.370(7) . ? S1' O3' 1.408(6) . ? S1' O1' 1.460(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 121.4(3) . . ? C1 N1 C21 122.5(3) . . ? C1 N1 C8 117.3(3) . . ? C21 N1 C8 120.2(2) . . ? C3 C2 C7 120.1(3) . . ? C3 C2 C1 116.8(3) . . ? C7 C2 C1 121.7(3) . . ? N2 C3 C4 123.4(3) . . ? N2 C3 C2 117.6(3) . . ? C4 C3 C2 118.8(3) . . ? C5 C4 C3 119.2(4) . . ? C4 C5 C6 122.3(4) . . ? C7 C6 C5 119.3(4) . . ? C6 C7 C2 120.3(4) . . ? N2 C8 N1 106.9(3) . . ? N2 C8 C9 112.3(3) . . ? N1 C8 C9 109.9(2) . . ? C3 N2 C8 118.4(3) . . ? C11 C9 C10 114.2(3) . . ? C11 C9 C8 111.6(3) . . ? C10 C9 C8 108.3(3) . . ? C12 C11 C16 118.3(3) . . ? C12 C11 C9 119.9(3) . . ? C16 C11 C9 121.8(3) . . ? C13 C12 C11 121.2(3) . . ? C14 C13 C12 119.9(3) . . ? C15 C14 C13 119.5(3) . . ? C16 C15 C14 120.5(3) . . ? C15 C16 C11 120.7(3) . . ? C26 C21 C22 121.4(3) . . ? C26 C21 N1 119.2(3) . . ? C22 C21 N1 119.4(3) . . ? C21 C22 C23 118.3(3) . . ? C24 C23 C22 122.0(3) . . ? C25 C24 C23 117.6(3) . . ? C25 C24 C27 121.3(4) . . ? C23 C24 C27 121.2(4) . . ? C26 C25 C24 122.0(3) . . ? C21 C26 C25 118.7(3) . . ? F3 C99 F2 106.6(5) . . ? F3 C99 F1 107.7(5) . . ? F2 C99 F1 113.0(5) . . ? F3 C99 S1 111.0(4) . . ? F2 C99 S1 108.7(5) . . ? F1 C99 S1 109.8(4) . . ? O3 S1 O1 113.4(4) . . ? O3 S1 O2 124.5(4) . . ? O1 S1 O2 111.6(4) . . ? O3 S1 C99 104.0(3) . . ? O1 S1 C99 105.9(3) . . ? O2 S1 C99 93.0(4) . . ? F1' C99' F2' 100.1(7) . . ? F1' C99' F3' 101.5(8) . . ? F2' C99' F3' 104.1(7) . . ? F1' C99' S1' 118.0(7) . . ? F2' C99' S1' 114.7(7) . . ? F3' C99' S1' 116.2(7) . . ? O2' S1' O3' 107.1(5) . . ? O2' S1' O1' 117.4(5) . . ? O3' S1' O1' 113.5(4) . . ? O2' S1' C99' 115.7(5) . . ? O3' S1' C99' 101.0(4) . . ? O1' S1' C99' 101.1(5) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.303 _refine_diff_density_min -0.985 _refine_diff_density_rms 0.084 # Attachment '3d4.cif' data_j30s _database_code_depnum_ccdc_archive 'CCDC 800055' #TrackingRef '3d4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H23 F3 N2 O3 S' _chemical_formula_weight 392.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.9025(11) _cell_length_b 13.0141(13) _cell_length_c 13.1294(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.094(2) _cell_angle_gamma 90.00 _cell_volume 1852.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5469 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 27.65 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8676 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21913 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 28.70 _reflns_number_total 4547 _reflns_number_gt 3698 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.9260P] 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 'NH free, rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4547 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.22462(15) 0.49314(12) 0.09481(12) 0.0188(3) Uani 1 1 d . . . N1 N 0.24468(13) 0.39814(11) 0.12731(10) 0.0190(3) Uani 1 1 d . . . C2 C 0.12398(15) 0.55022(13) 0.13016(13) 0.0200(3) Uani 1 1 d . . . C3 C 0.03245(16) 0.49385(13) 0.17539(13) 0.0220(3) Uani 1 1 d . . . N2 N 0.05914(14) 0.39608(12) 0.20451(12) 0.0249(3) Uani 1 1 d . . . H02 H 0.005(2) 0.3561(17) 0.2203(18) 0.035(6) Uiso 1 1 d . . . C4 C -0.08242(16) 0.53984(15) 0.18609(14) 0.0259(4) Uani 1 1 d . . . H4 H -0.1463 0.5009 0.2115 0.031 Uiso 1 1 calc R . . C5 C -0.10168(17) 0.64085(15) 0.15981(14) 0.0281(4) Uani 1 1 d . . . H5 H -0.1789 0.6718 0.1681 0.034 Uiso 1 1 calc R . . C6 C -0.00900(17) 0.69947(14) 0.12078(14) 0.0265(4) Uani 1 1 d . . . H6 H -0.0226 0.7702 0.1054 0.032 Uiso 1 1 calc R . . C7 C 0.10101(16) 0.65439(13) 0.10495(13) 0.0229(4) Uani 1 1 d . . . H7 H 0.1625 0.6937 0.0767 0.028 Uiso 1 1 calc R . . C8 C 0.18587(16) 0.36602(13) 0.22002(13) 0.0223(4) Uani 1 1 d . . . H8 H 0.1901 0.2894 0.2257 0.027 Uiso 1 1 calc R . . C9 C 0.29960(16) 0.53886(13) 0.01781(13) 0.0217(3) Uani 1 1 d . . . H9A H 0.3842 0.5126 0.0291 0.033 Uiso 1 1 calc R . . H9B H 0.3005 0.6138 0.0249 0.033 Uiso 1 1 calc R . . H9C H 0.2634 0.5202 -0.0513 0.033 Uiso 1 1 calc R . . C10 C 0.25511(17) 0.41254(14) 0.31584(13) 0.0260(4) Uani 1 1 d . . . H10A H 0.2530 0.4877 0.3107 0.039 Uiso 1 1 calc R . . H10B H 0.3410 0.3890 0.3224 0.039 Uiso 1 1 calc R . . H10C H 0.2160 0.3909 0.3762 0.039 Uiso 1 1 calc R . . C11 C 0.32265(15) 0.32383(12) 0.07600(13) 0.0195(3) Uani 1 1 d . . . H11 H 0.3255 0.3482 0.0041 0.023 Uiso 1 1 calc R . . C12 C 0.26642(16) 0.21627(13) 0.07019(14) 0.0226(4) Uani 1 1 d . . . H12A H 0.1796 0.2197 0.0395 0.027 Uiso 1 1 calc R . . H12B H 0.2679 0.1869 0.1399 0.027 Uiso 1 1 calc R . . C13 C 0.34099(17) 0.14823(13) 0.00459(14) 0.0251(4) Uani 1 1 d . . . H13A H 0.3050 0.0783 0.0002 0.030 Uiso 1 1 calc R . . H13B H 0.3369 0.1766 -0.0656 0.030 Uiso 1 1 calc R . . C14 C 0.47509(17) 0.14236(13) 0.05057(15) 0.0272(4) Uani 1 1 d . . . H14A H 0.5230 0.1015 0.0050 0.033 Uiso 1 1 calc R . . H14B H 0.4798 0.1072 0.1177 0.033 Uiso 1 1 calc R . . C15 C 0.53141(17) 0.24945(14) 0.06465(16) 0.0291(4) Uani 1 1 d . . . H15A H 0.5379 0.2804 -0.0035 0.035 Uiso 1 1 calc R . . H15B H 0.6158 0.2436 0.1003 0.035 Uiso 1 1 calc R . . C16 C 0.45478(16) 0.32014(13) 0.12631(15) 0.0251(4) Uani 1 1 d . . . H16A H 0.4561 0.2942 0.1973 0.030 Uiso 1 1 calc R . . H16B H 0.4905 0.3901 0.1291 0.030 Uiso 1 1 calc R . . C99 C 0.60162(17) 0.57976(14) 0.36626(14) 0.0275(4) Uani 1 1 d . . . F1 F 0.72414(10) 0.57689(9) 0.38293(10) 0.0390(3) Uani 1 1 d . . . F2 F 0.56094(14) 0.63335(13) 0.44222(9) 0.0550(4) Uani 1 1 d . . . F3 F 0.56092(12) 0.48439(10) 0.37163(11) 0.0513(4) Uani 1 1 d . . . S1 S 0.55170(4) 0.63829(3) 0.24254(3) 0.01906(12) Uani 1 1 d . . . O1 O 0.60079(12) 0.57037(10) 0.17072(10) 0.0310(3) Uani 1 1 d . . . O2 O 0.61015(12) 0.73791(9) 0.25094(11) 0.0289(3) Uani 1 1 d . . . O3 O 0.41936(11) 0.63996(10) 0.23915(10) 0.0265(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0210(8) 0.0171(8) 0.0184(8) -0.0023(6) 0.0033(6) -0.0047(6) N1 0.0211(7) 0.0176(6) 0.0193(7) -0.0002(5) 0.0078(5) -0.0027(5) C2 0.0194(8) 0.0205(8) 0.0204(8) -0.0020(6) 0.0039(6) -0.0021(6) C3 0.0227(8) 0.0232(8) 0.0206(8) -0.0030(6) 0.0043(6) -0.0050(7) N2 0.0224(7) 0.0222(7) 0.0320(8) 0.0009(6) 0.0111(6) -0.0059(6) C4 0.0194(8) 0.0331(10) 0.0255(9) -0.0028(7) 0.0036(7) -0.0038(7) C5 0.0211(8) 0.0357(10) 0.0269(9) -0.0043(8) 0.0005(7) 0.0031(7) C6 0.0287(9) 0.0233(9) 0.0267(9) -0.0013(7) -0.0006(7) 0.0034(7) C7 0.0249(8) 0.0223(8) 0.0218(8) -0.0005(6) 0.0036(7) -0.0024(7) C8 0.0274(9) 0.0183(8) 0.0231(8) 0.0022(6) 0.0113(7) -0.0015(7) C9 0.0262(9) 0.0178(8) 0.0220(8) -0.0003(6) 0.0074(7) -0.0041(6) C10 0.0309(9) 0.0261(9) 0.0219(9) 0.0012(7) 0.0068(7) 0.0011(7) C11 0.0239(8) 0.0167(7) 0.0187(8) -0.0006(6) 0.0066(6) -0.0004(6) C12 0.0225(8) 0.0190(8) 0.0266(9) -0.0028(7) 0.0030(7) -0.0044(6) C13 0.0330(10) 0.0179(8) 0.0250(9) -0.0026(6) 0.0058(7) -0.0025(7) C14 0.0303(10) 0.0188(8) 0.0334(10) 0.0003(7) 0.0080(8) 0.0019(7) C15 0.0216(9) 0.0227(9) 0.0440(11) -0.0035(8) 0.0088(8) -0.0017(7) C16 0.0210(8) 0.0216(8) 0.0329(10) -0.0044(7) 0.0041(7) -0.0051(7) C99 0.0251(9) 0.0311(10) 0.0265(9) 0.0058(7) 0.0032(7) -0.0027(7) F1 0.0243(6) 0.0430(7) 0.0473(7) 0.0154(6) -0.0075(5) -0.0010(5) F2 0.0574(9) 0.0878(11) 0.0209(6) -0.0033(6) 0.0090(6) 0.0096(8) F3 0.0433(7) 0.0418(7) 0.0666(9) 0.0300(7) -0.0044(6) -0.0143(6) S1 0.0189(2) 0.0195(2) 0.0196(2) -0.00091(15) 0.00579(15) 0.00299(15) O1 0.0293(7) 0.0351(7) 0.0302(7) -0.0115(6) 0.0106(5) 0.0035(6) O2 0.0263(7) 0.0196(6) 0.0424(8) 0.0028(5) 0.0106(6) 0.0020(5) O3 0.0204(6) 0.0305(7) 0.0288(7) -0.0026(5) 0.0037(5) 0.0036(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.319(2) . ? C1 C2 1.442(2) . ? C1 C9 1.490(2) . ? N1 C11 1.494(2) . ? N1 C8 1.494(2) . ? C2 C7 1.412(2) . ? C2 C3 1.419(2) . ? C3 N2 1.351(2) . ? C3 C4 1.408(2) . ? N2 C8 1.430(2) . ? C4 C5 1.370(3) . ? C5 C6 1.405(3) . ? C6 C7 1.371(2) . ? C8 C10 1.522(3) . ? C11 C16 1.520(2) . ? C11 C12 1.527(2) . ? C12 C13 1.528(2) . ? C13 C14 1.523(3) . ? C14 C15 1.526(2) . ? C15 C16 1.531(2) . ? C99 F3 1.323(2) . ? C99 F2 1.331(2) . ? C99 F1 1.331(2) . ? C99 S1 1.8240(19) . ? S1 O1 1.4367(13) . ? S1 O3 1.4390(13) . ? S1 O2 1.4437(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 118.99(14) . . ? N1 C1 C9 120.66(15) . . ? C2 C1 C9 120.25(14) . . ? C1 N1 C11 122.93(13) . . ? C1 N1 C8 117.07(13) . . ? C11 N1 C8 119.99(13) . . ? C7 C2 C3 118.66(15) . . ? C7 C2 C1 122.78(15) . . ? C3 C2 C1 117.48(15) . . ? N2 C3 C4 122.61(16) . . ? N2 C3 C2 117.74(16) . . ? C4 C3 C2 119.64(16) . . ? C3 N2 C8 118.28(14) . . ? C5 C4 C3 119.80(17) . . ? C4 C5 C6 121.05(17) . . ? C7 C6 C5 119.84(17) . . ? C6 C7 C2 120.78(16) . . ? N2 C8 N1 107.40(14) . . ? N2 C8 C10 113.32(14) . . ? N1 C8 C10 110.11(14) . . ? N1 C11 C16 112.50(13) . . ? N1 C11 C12 111.79(13) . . ? C16 C11 C12 110.46(14) . . ? C11 C12 C13 108.94(14) . . ? C14 C13 C12 110.57(14) . . ? C13 C14 C15 111.04(14) . . ? C14 C15 C16 112.19(15) . . ? C11 C16 C15 109.53(14) . . ? F3 C99 F2 108.15(16) . . ? F3 C99 F1 107.54(15) . . ? F2 C99 F1 107.45(16) . . ? F3 C99 S1 111.67(13) . . ? F2 C99 S1 110.91(13) . . ? F1 C99 S1 110.94(12) . . ? O1 S1 O3 115.54(8) . . ? O1 S1 O2 114.23(8) . . ? O3 S1 O2 114.95(8) . . ? O1 S1 C99 103.36(9) . . ? O3 S1 C99 103.72(8) . . ? O2 S1 C99 102.68(8) . . ? 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 C2 C1 N1 C11 163.44(15) . . . . ? C9 C1 N1 C11 -12.8(2) . . . . ? C2 C1 N1 C8 -16.8(2) . . . . ? C9 C1 N1 C8 166.92(14) . . . . ? N1 C1 C2 C7 175.55(15) . . . . ? C9 C1 C2 C7 -8.2(2) . . . . ? N1 C1 C2 C3 -16.5(2) . . . . ? C9 C1 C2 C3 159.77(15) . . . . ? C7 C2 C3 N2 -176.15(15) . . . . ? C1 C2 C3 N2 15.4(2) . . . . ? C7 C2 C3 C4 5.4(2) . . . . ? C1 C2 C3 C4 -163.12(15) . . . . ? C4 C3 N2 C8 -161.36(16) . . . . ? C2 C3 N2 C8 20.2(2) . . . . ? N2 C3 C4 C5 176.77(17) . . . . ? C2 C3 C4 C5 -4.8(3) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C4 C5 C6 C7 2.5(3) . . . . ? C5 C6 C7 C2 -1.8(3) . . . . ? C3 C2 C7 C6 -2.0(2) . . . . ? C1 C2 C7 C6 165.78(16) . . . . ? C3 N2 C8 N1 -50.2(2) . . . . ? C3 N2 C8 C10 71.6(2) . . . . ? C1 N1 C8 N2 48.46(19) . . . . ? C11 N1 C8 N2 -131.79(15) . . . . ? C1 N1 C8 C10 -75.36(18) . . . . ? C11 N1 C8 C10 104.39(17) . . . . ? C1 N1 C11 C16 95.85(18) . . . . ? C8 N1 C11 C16 -83.87(18) . . . . ? C1 N1 C11 C12 -139.18(16) . . . . ? C8 N1 C11 C12 41.1(2) . . . . ? N1 C11 C12 C13 172.43(14) . . . . ? C16 C11 C12 C13 -61.48(18) . . . . ? C11 C12 C13 C14 59.37(19) . . . . ? C12 C13 C14 C15 -55.7(2) . . . . ? C13 C14 C15 C16 53.8(2) . . . . ? N1 C11 C16 C15 -175.37(14) . . . . ? C12 C11 C16 C15 58.94(19) . . . . ? C14 C15 C16 C11 -55.0(2) . . . . ? F3 C99 S1 O1 -58.14(15) . . . . ? F2 C99 S1 O1 -178.84(13) . . . . ? F1 C99 S1 O1 61.81(15) . . . . ? F3 C99 S1 O3 62.80(15) . . . . ? F2 C99 S1 O3 -57.91(15) . . . . ? F1 C99 S1 O3 -177.25(13) . . . . ? F3 C99 S1 O2 -177.21(13) . . . . ? F2 C99 S1 O2 62.09(15) . . . . ? F1 C99 S1 O2 -57.25(15) . . . . ? 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 N2 H02 O2 0.83(2) 2.05(2) 2.8663(19) 170(2) 2_545 C8 H8 O3 1.00 2.35 3.223(2) 144.9 2_545 C9 H9C O1 0.98 2.56 3.146(2) 118.7 3_665 _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.518 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.061 # Attachment '6d.cif' data_aiff _database_code_depnum_ccdc_archive 'CCDC 800056' #TrackingRef '6d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C75 H79 Cl8 F9 N6 O9 S3' _chemical_formula_weight 1759.22 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 Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.531(2) _cell_length_b 17.185(2) _cell_length_c 19.511(2) _cell_angle_alpha 108.267(13) _cell_angle_beta 106.724(13) _cell_angle_gamma 101.091(14) _cell_volume 3921.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 20148 _cell_measurement_theta_min 3.5461 _cell_measurement_theta_max 75.6340 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1816 _exptl_absorpt_coefficient_mu 4.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.56041 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 83238 _diffrn_reflns_av_R_equivalents 0.0761 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 75.82 _reflns_number_total 16034 _reflns_number_gt 10409 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens XP' _computing_publication_material SHELXL-97 _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. Refinement of the solvent sites proved difficult. One chloroform (at C82) is well-ordered. The molecules at C81 and C83 were interpreted as disordered dichloromethane and chloroform respectively. A system of restraints was used to improve stability of refinement, but the results are not entirely satisfactory (see e.g. U values). However, we prefer this model to the use of SQUEEZE. The triflates are all well-ordered. ; _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^)+(0.1190P)^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 'NH free with SADI, rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 16034 _refine_ls_number_parameters 1031 _refine_ls_number_restraints 931 _refine_ls_R_factor_all 0.0942 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1843 _refine_ls_wR_factor_gt 0.1666 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.970 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.1373(2) 0.19445(17) 0.05662(14) 0.0268(6) Uani 1 1 d DU . . H02 H 0.126(3) 0.1419(19) 0.048(2) 0.039(11) Uiso 1 1 d D . . N1 N 0.2786(2) 0.28718(15) 0.04242(13) 0.0228(5) Uani 1 1 d U . . C1 C 0.2058(2) 0.31159(19) 0.00047(16) 0.0238(6) Uani 1 1 d U . . C2 C 0.0988(3) 0.2965(2) 0.00361(16) 0.0257(6) Uani 1 1 d U . . C3 C 0.0618(3) 0.2286(2) 0.02544(16) 0.0273(7) Uani 1 1 d U . . C4 C -0.0490(3) 0.1968(2) 0.01048(19) 0.0345(8) Uani 1 1 d U . . H4 H -0.0758 0.1472 0.0196 0.041 Uiso 1 1 calc R . . C5 C -0.1185(3) 0.2381(3) -0.0175(2) 0.0399(8) Uani 1 1 d U . . H5 H -0.1932 0.2177 -0.0258 0.048 Uiso 1 1 calc R . . C6 C -0.0814(3) 0.3098(2) -0.0341(2) 0.0375(8) Uani 1 1 d U . . H6 H -0.1298 0.3392 -0.0512 0.045 Uiso 1 1 calc R . . C7 C 0.0255(3) 0.3369(2) -0.02524(18) 0.0320(7) Uani 1 1 d U . . H7 H 0.0501 0.3834 -0.0388 0.038 Uiso 1 1 calc R . . C8 C 0.2483(3) 0.24749(19) 0.09441(16) 0.0237(6) Uani 1 1 d U . . H8 H 0.2941 0.2093 0.1022 0.028 Uiso 1 1 calc R . . C9 C 0.2274(3) 0.3472(2) -0.05635(17) 0.0283(7) Uani 1 1 d U . . H9A H 0.2284 0.4075 -0.0395 0.042 Uiso 1 1 calc R . . H9B H 0.1701 0.3136 -0.1079 0.042 Uiso 1 1 calc R . . H9C H 0.2978 0.3439 -0.0589 0.042 Uiso 1 1 calc R . . C11 C 0.3889(3) 0.2929(2) 0.03955(17) 0.0246(6) Uani 1 1 d U . . H11 H 0.4094 0.3399 0.0216 0.029 Uiso 1 1 calc R . . C12 C 0.4753(3) 0.3159(2) 0.11975(18) 0.0292(7) Uani 1 1 d U . . H12A H 0.4766 0.3707 0.1573 0.035 Uiso 1 1 calc R . . H12B H 0.4581 0.2701 0.1390 0.035 Uiso 1 1 calc R . . C13 C 0.5857(3) 0.3248(2) 0.1122(2) 0.0357(8) Uani 1 1 d U . . H13A H 0.6035 0.3720 0.0947 0.043 Uiso 1 1 calc R . . H13B H 0.6423 0.3398 0.1637 0.043 Uiso 1 1 calc R . . C14 C 0.5854(3) 0.2418(3) 0.0547(2) 0.0394(8) Uani 1 1 d U . . H14A H 0.5730 0.1955 0.0742 0.047 Uiso 1 1 calc R . . H14B H 0.6571 0.2495 0.0497 0.047 Uiso 1 1 calc R . . C15 C 0.4966(3) 0.2152(2) -0.0252(2) 0.0369(8) Uani 1 1 d U . . H15A H 0.5141 0.2581 -0.0475 0.044 Uiso 1 1 calc R . . H15B H 0.4946 0.1587 -0.0606 0.044 Uiso 1 1 calc R . . C16 C 0.3857(3) 0.2089(2) -0.01983(18) 0.0285(7) Uani 1 1 d U . . H16A H 0.3635 0.1608 -0.0043 0.034 Uiso 1 1 calc R . . H16B H 0.3314 0.1967 -0.0714 0.034 Uiso 1 1 calc R . . N1' N 0.1814(2) 0.29107(16) 0.72121(13) 0.0225(5) Uani 1 1 d U . . N2' N 0.2413(2) 0.43200(17) 0.82172(14) 0.0268(6) Uani 1 1 d DU . . H02' H 0.294(3) 0.465(2) 0.8629(19) 0.040(11) Uiso 1 1 d D . . C1' C 0.0795(3) 0.2858(2) 0.71070(17) 0.0255(6) Uani 1 1 d U . . C2' C 0.0532(3) 0.3621(2) 0.74758(18) 0.0304(7) Uani 1 1 d U . . C3' C 0.1385(3) 0.4328(2) 0.80937(18) 0.0310(7) Uani 1 1 d U . . C4' C 0.1136(4) 0.4995(3) 0.8590(2) 0.0433(9) Uani 1 1 d U . . H4' H 0.1699 0.5453 0.9028 0.052 Uiso 1 1 calc R . . C5' C 0.0072(4) 0.4972(3) 0.8430(3) 0.0569(11) Uani 1 1 d U . . H5' H -0.0095 0.5423 0.8759 0.068 Uiso 1 1 calc R . . C6' C -0.0764(4) 0.4308(3) 0.7799(3) 0.0604(12) Uani 1 1 d U . . H6' H -0.1491 0.4321 0.7688 0.073 Uiso 1 1 calc R . . C7' C -0.0547(3) 0.3626(3) 0.7331(2) 0.0437(9) Uani 1 1 d U . . H7' H -0.1126 0.3161 0.6911 0.052 Uiso 1 1 calc R . . C8' C 0.2661(3) 0.37707(19) 0.76071(16) 0.0236(6) Uani 1 1 d U . . H8' H 0.3364 0.3683 0.7857 0.028 Uiso 1 1 calc R . . C9' C -0.0090(3) 0.2010(2) 0.6641(2) 0.0337(7) Uani 1 1 d U . . H9'1 H -0.0323 0.1906 0.6087 0.051 Uiso 1 1 calc R . . H9'2 H -0.0708 0.2025 0.6806 0.051 Uiso 1 1 calc R . . H9'3 H 0.0183 0.1547 0.6727 0.051 Uiso 1 1 calc R . . N1" N 0.8086(2) 1.02090(16) 0.70430(14) 0.0241(5) Uani 1 1 d U . . N2" N 0.7891(2) 0.99798(16) 0.57414(15) 0.0244(5) Uani 1 1 d DU . . H02" H 0.830(3) 0.993(2) 0.5498(18) 0.017(8) Uiso 1 1 d D . . C1" C 0.7513(3) 1.0741(2) 0.7041(2) 0.0313(7) Uani 1 1 d U . . C2" C 0.6869(3) 1.0746(2) 0.6309(2) 0.0306(7) Uani 1 1 d U . . C3" C 0.7175(2) 1.0422(2) 0.56693(18) 0.0260(6) Uani 1 1 d U . . C4" C 0.6773(3) 1.0609(2) 0.5007(2) 0.0325(7) Uani 1 1 d U . . H4" H 0.7033 1.0444 0.4597 0.039 Uiso 1 1 calc R . . C5" C 0.6013(3) 1.1026(3) 0.4959(2) 0.0426(9) Uani 1 1 d U . . H5" H 0.5730 1.1134 0.4505 0.051 Uiso 1 1 calc R . . C6" C 0.5644(3) 1.1296(3) 0.5557(3) 0.0480(10) Uani 1 1 d U . . H6" H 0.5088 1.1562 0.5500 0.058 Uiso 1 1 calc R . . C7" C 0.6081(3) 1.1181(3) 0.6235(3) 0.0430(9) Uani 1 1 d U . . H7" H 0.5852 1.1396 0.6655 0.052 Uiso 1 1 calc R . . C8" C 0.7979(2) 0.95735(18) 0.62867(16) 0.0217(6) Uani 1 1 d U . . H8" H 0.8663 0.9413 0.6366 0.026 Uiso 1 1 calc R . . C9" C 0.7604(4) 1.1405(2) 0.7789(2) 0.0438(9) Uani 1 1 d U . . H9"1 H 0.7278 1.1120 0.8070 0.066 Uiso 1 1 calc R . . H9"2 H 0.7223 1.1808 0.7677 0.066 Uiso 1 1 calc R . . H9"3 H 0.8371 1.1721 0.8109 0.066 Uiso 1 1 calc R . . C101 C 0.3487(2) 0.48989(18) 0.40913(15) 0.0189(6) Uani 1 1 d U . . C102 C 0.3164(2) 0.46333(18) 0.46267(16) 0.0204(6) Uani 1 1 d U . . H102 H 0.2676 0.4072 0.4452 0.024 Uiso 1 1 calc R . . C103 C 0.3547(2) 0.51774(18) 0.54061(15) 0.0183(5) Uani 1 1 d U . . C104 C 0.4256(2) 0.60061(18) 0.56569(15) 0.0191(6) Uani 1 1 d U . . H104 H 0.4516 0.6383 0.6189 0.023 Uiso 1 1 calc R . . C105 C 0.4587(2) 0.62877(17) 0.51381(15) 0.0183(5) Uani 1 1 d U . . C106 C 0.4194(2) 0.57262(18) 0.43558(16) 0.0201(6) Uani 1 1 d U . . H106 H 0.4413 0.5913 0.3998 0.024 Uiso 1 1 calc R . . C21 C 0.3149(2) 0.42899(18) 0.32686(15) 0.0192(6) Uani 1 1 d U . . C22 C 0.3048(2) 0.45799(18) 0.26665(16) 0.0212(6) Uani 1 1 d U . . H22 H 0.3124 0.5172 0.2773 0.025 Uiso 1 1 calc R . . C23 C 0.2840(2) 0.40219(19) 0.19149(16) 0.0228(6) Uani 1 1 d U . . H23 H 0.2786 0.4235 0.1516 0.027 Uiso 1 1 calc R . . C24 C 0.2711(2) 0.31568(19) 0.17463(16) 0.0216(6) Uani 1 1 d U . . C25 C 0.2793(2) 0.28566(19) 0.23381(16) 0.0230(6) Uani 1 1 d U . . H25 H 0.2702 0.2262 0.2226 0.028 Uiso 1 1 calc R . . C26 C 0.3006(2) 0.34124(18) 0.30885(16) 0.0223(6) Uani 1 1 d U . . H26 H 0.3055 0.3195 0.3485 0.027 Uiso 1 1 calc R . . C31 C 0.3255(2) 0.48549(17) 0.59735(16) 0.0193(6) Uani 1 1 d U . . C32 C 0.2235(2) 0.42880(19) 0.57741(16) 0.0228(6) Uani 1 1 d U . . H32 H 0.1686 0.4135 0.5281 0.027 Uiso 1 1 calc R . . C33 C 0.2011(2) 0.3943(2) 0.62916(17) 0.0245(6) Uani 1 1 d U . . H33 H 0.1311 0.3559 0.6148 0.029 Uiso 1 1 calc R . . C34 C 0.2804(2) 0.41542(18) 0.70161(16) 0.0216(6) Uani 1 1 d U . . C35 C 0.3812(2) 0.47279(19) 0.72226(16) 0.0223(6) Uani 1 1 d U . . H35 H 0.4356 0.4883 0.7719 0.027 Uiso 1 1 calc R . . C36 C 0.4039(2) 0.50820(18) 0.67114(16) 0.0211(6) Uani 1 1 d U . . H36 H 0.4733 0.5481 0.6865 0.025 Uiso 1 1 calc R . . C41 C 0.5405(2) 0.71483(17) 0.54189(15) 0.0186(5) Uani 1 1 d U . . C42 C 0.5459(2) 0.78471(19) 0.60453(16) 0.0214(6) Uani 1 1 d U . . H42 H 0.4938 0.7784 0.6279 0.026 Uiso 1 1 calc R . . C43 C 0.6264(2) 0.86401(19) 0.63375(17) 0.0227(6) Uani 1 1 d U . . H43 H 0.6288 0.9109 0.6767 0.027 Uiso 1 1 calc R . . C44 C 0.7030(2) 0.87419(18) 0.59992(16) 0.0204(6) Uani 1 1 d U . . C45 C 0.6971(2) 0.80494(19) 0.53677(16) 0.0211(6) Uani 1 1 d U . . H45 H 0.7487 0.8115 0.5130 0.025 Uiso 1 1 calc R . . C46 C 0.6174(2) 0.72663(18) 0.50795(16) 0.0206(6) Uani 1 1 d U . . H46 H 0.6147 0.6802 0.4646 0.025 Uiso 1 1 calc R . . C61' C 0.2200(3) 0.2147(2) 0.69776(17) 0.0252(6) Uani 1 1 d U . . H61' H 0.1565 0.1651 0.6567 0.030 Uiso 1 1 calc R . . C62' C 0.3070(3) 0.2300(2) 0.6638(2) 0.0325(7) Uani 1 1 d U . . H62A H 0.2781 0.2437 0.6178 0.039 Uiso 1 1 calc R . . H62B H 0.3707 0.2793 0.7029 0.039 Uiso 1 1 calc R . . C63' C 0.3404(3) 0.1491(3) 0.6404(2) 0.0389(8) Uani 1 1 d U . . H63A H 0.3964 0.1582 0.6180 0.047 Uiso 1 1 calc R . . H63B H 0.2768 0.1005 0.6000 0.047 Uiso 1 1 calc R . . C64' C 0.3852(3) 0.1264(2) 0.7104(2) 0.0375(8) Uani 1 1 d U . . H14' H 0.4063 0.0735 0.6938 0.045 Uiso 1 1 calc R . . H64B H 0.4508 0.1738 0.7499 0.045 Uiso 1 1 calc R . . C65' C 0.3003(3) 0.1119(2) 0.74605(19) 0.0326(7) Uani 1 1 d U . . H64A H 0.3322 0.1011 0.7933 0.039 Uiso 1 1 calc R . . H65B H 0.2381 0.0605 0.7085 0.039 Uiso 1 1 calc R . . C66' C 0.2602(3) 0.1911(2) 0.76758(17) 0.0266(6) Uani 1 1 d U . . H65A H 0.2006 0.1783 0.7861 0.032 Uiso 1 1 calc R . . H66B H 0.3203 0.2406 0.8104 0.032 Uiso 1 1 calc R . . C71 C 0.8904(3) 1.0212(2) 0.77587(17) 0.0275(7) Uani 1 1 d U . . H71 H 0.8755 1.0540 0.8221 0.033 Uiso 1 1 calc R . . C72 C 0.8793(3) 0.9297(2) 0.77227(19) 0.0315(7) Uani 1 1 d U . . H72A H 0.8069 0.9037 0.7716 0.038 Uiso 1 1 calc R . . H72B H 0.8853 0.8940 0.7237 0.038 Uiso 1 1 calc R . . C73 C 0.9672(3) 0.9301(3) 0.8420(2) 0.0403(8) Uani 1 1 d U . . H73A H 0.9576 0.9618 0.8904 0.048 Uiso 1 1 calc R . . H73B H 0.9602 0.8701 0.8376 0.048 Uiso 1 1 calc R . . C74 C 1.0795(3) 0.9727(3) 0.8461(2) 0.0444(9) Uani 1 1 d U . . H74A H 1.1356 0.9726 0.8917 0.053 Uiso 1 1 calc R . . H74B H 1.0904 0.9396 0.7987 0.053 Uiso 1 1 calc R . . C75 C 1.0912(3) 1.0641(3) 0.8528(2) 0.0412(9) Uani 1 1 d U . . H75A H 1.1638 1.0904 0.8537 0.049 Uiso 1 1 calc R . . H75B H 1.0864 1.0981 0.9024 0.049 Uiso 1 1 calc R . . C76 C 1.0041(3) 1.0686(2) 0.78536(19) 0.0348(8) Uani 1 1 d U . . H76A H 1.0103 1.1297 0.7948 0.042 Uiso 1 1 calc R . . H76B H 1.0161 1.0427 0.7366 0.042 Uiso 1 1 calc R . . S1 S 0.42687(6) 0.56418(5) 1.07369(4) 0.02843(18) Uani 1 1 d U . . O1 O 0.4233(2) 0.48996(15) 1.09319(13) 0.0375(6) Uani 1 1 d U . . O2 O 0.53292(19) 0.62581(16) 1.10374(14) 0.0367(6) Uani 1 1 d U . . O3 O 0.3610(2) 0.54747(16) 0.99501(13) 0.0385(6) Uani 1 1 d U . . C97 C 0.3564(3) 0.6194(2) 1.1300(2) 0.0382(8) Uani 1 1 d U . . F1 F 0.4062(2) 0.64024(17) 1.20632(14) 0.0581(6) Uani 1 1 d U . . F2 F 0.25461(19) 0.56912(17) 1.10841(16) 0.0560(6) Uani 1 1 d U . . F3 F 0.3501(2) 0.69265(15) 1.12082(16) 0.0531(6) Uani 1 1 d U . . S2 S 0.97880(7) 1.08033(6) 0.45088(5) 0.0358(2) Uani 1 1 d U . . O4 O 1.0878(2) 1.1165(2) 0.50832(15) 0.0489(7) Uani 1 1 d U . . O5 O 0.9663(2) 1.00906(19) 0.38291(16) 0.0475(7) Uani 1 1 d U . . O6 O 0.8938(2) 1.06978(19) 0.48014(16) 0.0473(7) Uani 1 1 d U . . C98 C 0.9648(3) 1.1653(3) 0.4161(2) 0.0479(10) Uani 1 1 d U . . F4 F 1.0369(3) 1.1805(2) 0.38300(17) 0.0681(8) Uani 1 1 d U . . F5 F 0.9831(3) 1.23837(18) 0.47395(19) 0.0743(8) Uani 1 1 d U . . F6 F 0.8669(3) 1.1457(2) 0.36340(19) 0.0819(9) Uani 1 1 d U . . S3 S 0.29431(8) 0.03639(6) 0.09941(6) 0.0376(2) Uani 1 1 d U . . O7 O 0.3749(2) 0.12010(16) 0.14206(16) 0.0434(6) Uani 1 1 d U . . O8 O 0.1933(2) 0.03612(17) 0.04799(18) 0.0477(7) Uani 1 1 d U . . O9 O 0.2832(3) -0.0154(2) 0.1427(2) 0.0602(9) Uani 1 1 d U . . C99 C 0.3517(3) -0.0214(2) 0.0330(3) 0.0418(9) Uani 1 1 d U . . F7 F 0.4457(2) -0.02694(17) 0.07201(18) 0.0636(7) Uani 1 1 d U . . F8 F 0.2856(2) -0.10057(14) -0.01288(17) 0.0589(7) Uani 1 1 d U . . F9 F 0.3690(3) 0.01866(16) -0.01246(17) 0.0631(7) Uani 1 1 d U . . C81 C 0.1553(5) -0.3921(3) 0.4466(3) 0.0443(13) Uani 0.747(4) 1 d PDU A 1 H81A H 0.2062 -0.4254 0.4388 0.053 Uiso 0.747(4) 1 calc PR A 1 H81B H 0.0939 -0.4129 0.3962 0.053 Uiso 0.747(4) 1 calc PR A 1 Cl1 Cl 0.22233(12) -0.28255(9) 0.47386(9) 0.0488(5) Uani 0.747(4) 1 d PDU A 1 Cl2 Cl 0.10576(14) -0.41232(10) 0.51536(10) 0.0598(6) Uani 0.747(4) 1 d PDU A 1 C81' C 0.176(2) -0.3557(17) 0.5226(14) 0.116(9) Uiso 0.253(4) 1 d PDU A 2 H81C H 0.1500 -0.3296 0.5644 0.140 Uiso 0.253(4) 1 calc PR A 2 H81D H 0.2286 -0.3837 0.5419 0.140 Uiso 0.253(4) 1 calc PR A 2 Cl1' Cl 0.236(2) -0.2769(17) 0.4959(19) 0.296(12) Uiso 0.253(4) 1 d PDU A 2 Cl2' Cl 0.0660(8) -0.4314(6) 0.4398(6) 0.124(3) Uiso 0.253(4) 1 d PDU A 2 C82 C 0.6157(4) -0.8535(3) 0.2377(3) 0.0502(10) Uani 1 1 d . . . H82 H 0.5441 -0.8644 0.1969 0.060 Uiso 1 1 calc R . . Cl3 Cl 0.66576(11) -0.74381(8) 0.29601(9) 0.0703(4) Uani 1 1 d . . . Cl4 Cl 0.59403(13) -0.91614(9) 0.29018(9) 0.0710(4) Uani 1 1 d . . . Cl5 Cl 0.70181(11) -0.88439(10) 0.19036(7) 0.0718(4) Uani 1 1 d . . . C83 C 0.9191(5) 0.3377(4) 0.2775(4) 0.0499(15) Uiso 0.699(6) 1 d PDU B 1 H83 H 0.8773 0.2934 0.2905 0.060 Uiso 0.699(6) 1 calc PR B 1 Cl6 Cl 0.87358(14) 0.42743(11) 0.29644(10) 0.0454(5) Uani 0.699(6) 1 d PDU B 1 Cl7 Cl 1.05572(16) 0.36818(18) 0.33330(19) 0.1018(11) Uani 0.699(6) 1 d PDU B 1 Cl8 Cl 0.9036(4) 0.29296(16) 0.17888(12) 0.1189(15) Uani 0.699(6) 1 d PDU B 1 C83' C 0.918(2) 0.3204(19) 0.2554(13) 0.160(13) Uiso 0.301(6) 1 d PDU B 2 H83' H 0.8525 0.2679 0.2298 0.192 Uiso 0.301(6) 1 calc PR B 2 Cl6' Cl 0.8863(16) 0.4160(13) 0.2888(12) 0.223(8) Uiso 0.301(6) 1 d PDU B 2 Cl7' Cl 1.0181(7) 0.3173(6) 0.3346(5) 0.115(3) Uiso 0.301(6) 1 d PDU B 2 Cl8' Cl 1.002(3) 0.3193(19) 0.2027(16) 0.360(14) Uiso 0.301(6) 1 d PDU B 2 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 N2 0.0324(14) 0.0207(13) 0.0201(12) 0.0063(10) 0.0073(10) 0.0000(11) N1 0.0293(13) 0.0212(12) 0.0154(11) 0.0071(9) 0.0085(10) 0.0026(10) C1 0.0286(15) 0.0209(14) 0.0140(12) 0.0034(11) 0.0050(11) 0.0014(12) C2 0.0294(15) 0.0249(14) 0.0151(13) 0.0041(11) 0.0060(11) 0.0020(12) C3 0.0324(16) 0.0272(15) 0.0155(13) 0.0039(11) 0.0092(12) 0.0021(13) C4 0.0310(17) 0.0379(18) 0.0247(15) 0.0082(14) 0.0080(13) 0.0002(14) C5 0.0297(17) 0.051(2) 0.0313(17) 0.0133(16) 0.0082(14) 0.0052(15) C6 0.0323(17) 0.044(2) 0.0304(17) 0.0117(15) 0.0069(14) 0.0105(15) C7 0.0349(17) 0.0308(16) 0.0218(15) 0.0063(13) 0.0068(13) 0.0048(13) C8 0.0299(15) 0.0231(14) 0.0168(13) 0.0094(11) 0.0089(11) 0.0027(12) C9 0.0324(16) 0.0309(16) 0.0181(14) 0.0114(12) 0.0063(12) 0.0038(13) C11 0.0279(15) 0.0255(15) 0.0206(14) 0.0108(12) 0.0099(12) 0.0049(12) C12 0.0301(16) 0.0297(16) 0.0216(14) 0.0092(12) 0.0070(12) 0.0018(13) C13 0.0285(16) 0.0374(18) 0.0353(18) 0.0166(15) 0.0058(14) 0.0029(14) C14 0.0364(19) 0.045(2) 0.044(2) 0.0218(17) 0.0176(16) 0.0166(16) C15 0.044(2) 0.0398(19) 0.0360(18) 0.0174(15) 0.0221(15) 0.0169(16) C16 0.0382(17) 0.0236(15) 0.0197(14) 0.0068(12) 0.0099(13) 0.0052(13) N1' 0.0261(13) 0.0236(12) 0.0166(11) 0.0099(9) 0.0079(9) 0.0017(10) N2' 0.0357(15) 0.0255(13) 0.0156(12) 0.0084(10) 0.0091(11) 0.0021(11) C1' 0.0283(15) 0.0319(16) 0.0178(13) 0.0132(12) 0.0094(12) 0.0057(12) C2' 0.0369(17) 0.0367(17) 0.0217(14) 0.0147(13) 0.0121(13) 0.0127(14) C3' 0.0461(19) 0.0322(16) 0.0204(14) 0.0142(13) 0.0151(13) 0.0139(14) C4' 0.063(2) 0.041(2) 0.0303(18) 0.0127(15) 0.0202(17) 0.0233(18) C5' 0.076(3) 0.059(3) 0.040(2) 0.0118(19) 0.023(2) 0.041(2) C6' 0.055(3) 0.079(3) 0.054(3) 0.021(2) 0.022(2) 0.042(2) C7' 0.042(2) 0.058(2) 0.0336(18) 0.0160(17) 0.0131(16) 0.0250(18) C8' 0.0290(15) 0.0223(14) 0.0153(13) 0.0084(11) 0.0069(11) -0.0007(12) C9' 0.0272(16) 0.0359(18) 0.0301(16) 0.0105(14) 0.0090(13) -0.0003(14) N1" 0.0291(13) 0.0205(12) 0.0214(12) 0.0084(10) 0.0108(10) 0.0023(10) N2" 0.0253(13) 0.0256(13) 0.0220(12) 0.0108(10) 0.0098(10) 0.0029(10) C1" 0.0409(18) 0.0228(15) 0.0347(17) 0.0132(13) 0.0204(14) 0.0065(13) C2" 0.0320(17) 0.0299(16) 0.0386(17) 0.0204(14) 0.0181(14) 0.0091(13) C3" 0.0227(14) 0.0252(15) 0.0283(15) 0.0132(12) 0.0086(12) 0.0005(12) C4" 0.0305(17) 0.0379(18) 0.0351(17) 0.0229(15) 0.0133(14) 0.0074(14) C5" 0.042(2) 0.053(2) 0.048(2) 0.0353(19) 0.0182(17) 0.0183(17) C6" 0.044(2) 0.058(2) 0.069(3) 0.044(2) 0.028(2) 0.0305(19) C7" 0.047(2) 0.047(2) 0.059(2) 0.0344(19) 0.0343(19) 0.0241(18) C8" 0.0242(14) 0.0209(13) 0.0200(13) 0.0092(11) 0.0095(11) 0.0031(11) C9" 0.075(3) 0.0319(18) 0.0387(19) 0.0160(15) 0.034(2) 0.0236(19) C101 0.0205(13) 0.0208(13) 0.0142(12) 0.0082(10) 0.0055(10) 0.0029(11) C102 0.0239(14) 0.0194(13) 0.0167(13) 0.0090(11) 0.0074(11) 0.0011(11) C103 0.0205(13) 0.0206(13) 0.0165(12) 0.0093(11) 0.0088(11) 0.0058(11) C104 0.0216(14) 0.0201(13) 0.0135(12) 0.0060(10) 0.0065(10) 0.0033(11) C105 0.0203(13) 0.0184(13) 0.0164(12) 0.0080(10) 0.0072(10) 0.0038(11) C106 0.0216(14) 0.0224(13) 0.0171(13) 0.0105(11) 0.0073(11) 0.0037(11) C21 0.0189(13) 0.0228(13) 0.0128(12) 0.0067(10) 0.0051(10) 0.0016(11) C22 0.0258(14) 0.0178(13) 0.0165(13) 0.0071(10) 0.0060(11) 0.0018(11) C23 0.0285(15) 0.0234(14) 0.0152(13) 0.0104(11) 0.0067(11) 0.0026(12) C24 0.0242(14) 0.0222(14) 0.0152(12) 0.0082(11) 0.0048(11) 0.0027(11) C25 0.0309(16) 0.0194(13) 0.0159(13) 0.0078(11) 0.0078(11) 0.0013(12) C26 0.0275(15) 0.0215(14) 0.0151(13) 0.0089(11) 0.0062(11) 0.0012(12) C31 0.0237(14) 0.0178(13) 0.0168(12) 0.0081(10) 0.0087(11) 0.0036(11) C32 0.0212(14) 0.0278(15) 0.0164(13) 0.0105(11) 0.0054(11) 0.0008(12) C33 0.0249(15) 0.0272(15) 0.0196(13) 0.0113(12) 0.0086(11) 0.0002(12) C34 0.0249(14) 0.0220(14) 0.0165(13) 0.0087(11) 0.0077(11) 0.0023(11) C35 0.0258(14) 0.0231(14) 0.0136(12) 0.0066(11) 0.0062(11) 0.0009(11) C36 0.0241(14) 0.0206(13) 0.0150(12) 0.0067(11) 0.0070(11) 0.0002(11) C41 0.0215(14) 0.0187(13) 0.0154(12) 0.0089(10) 0.0058(10) 0.0035(11) C42 0.0225(14) 0.0229(14) 0.0183(13) 0.0089(11) 0.0091(11) 0.0020(11) C43 0.0266(15) 0.0199(13) 0.0207(13) 0.0078(11) 0.0097(11) 0.0046(11) C44 0.0208(13) 0.0200(13) 0.0192(13) 0.0091(11) 0.0067(11) 0.0030(11) C45 0.0225(14) 0.0238(14) 0.0187(13) 0.0109(11) 0.0096(11) 0.0034(11) C46 0.0266(15) 0.0200(13) 0.0147(12) 0.0069(10) 0.0088(11) 0.0048(11) C61' 0.0279(15) 0.0243(14) 0.0185(13) 0.0068(11) 0.0069(12) 0.0030(12) C62' 0.0384(18) 0.0389(18) 0.0305(16) 0.0211(14) 0.0179(14) 0.0142(15) C63' 0.048(2) 0.051(2) 0.0321(18) 0.0208(16) 0.0222(16) 0.0261(18) C64' 0.041(2) 0.0408(19) 0.0372(18) 0.0178(15) 0.0166(15) 0.0201(16) C65' 0.0407(19) 0.0263(16) 0.0287(16) 0.0119(13) 0.0104(14) 0.0082(14) C66' 0.0309(16) 0.0259(15) 0.0230(14) 0.0125(12) 0.0101(12) 0.0035(12) C71 0.0291(16) 0.0303(16) 0.0190(14) 0.0087(12) 0.0081(12) 0.0032(13) C72 0.0326(17) 0.0338(17) 0.0261(16) 0.0171(13) 0.0061(13) 0.0044(14) C73 0.0396(19) 0.049(2) 0.0357(18) 0.0257(17) 0.0109(15) 0.0106(16) C74 0.0349(19) 0.071(3) 0.0311(18) 0.0275(18) 0.0102(15) 0.0166(18) C75 0.0319(18) 0.053(2) 0.0230(16) 0.0114(15) 0.0049(13) -0.0054(16) C76 0.0338(17) 0.0337(17) 0.0257(16) 0.0084(13) 0.0086(13) -0.0041(14) S1 0.0307(4) 0.0260(4) 0.0233(4) 0.0113(3) 0.0046(3) 0.0033(3) O1 0.0510(15) 0.0284(12) 0.0291(12) 0.0155(10) 0.0076(11) 0.0078(11) O2 0.0268(12) 0.0362(13) 0.0378(13) 0.0143(10) 0.0042(10) 0.0024(10) O3 0.0426(14) 0.0365(13) 0.0249(11) 0.0157(10) 0.0000(10) 0.0009(11) C97 0.0348(19) 0.0384(19) 0.043(2) 0.0178(16) 0.0151(16) 0.0092(15) F1 0.0725(17) 0.0640(16) 0.0390(12) 0.0161(11) 0.0251(12) 0.0243(13) F2 0.0391(13) 0.0611(15) 0.0814(18) 0.0399(14) 0.0300(12) 0.0131(11) F3 0.0561(15) 0.0426(12) 0.0731(16) 0.0271(12) 0.0319(13) 0.0228(11) S2 0.0275(4) 0.0469(5) 0.0271(4) 0.0103(4) 0.0103(3) 0.0062(4) O4 0.0288(13) 0.0726(19) 0.0361(14) 0.0243(13) 0.0065(11) -0.0002(13) O5 0.0500(16) 0.0513(16) 0.0384(14) 0.0092(12) 0.0224(12) 0.0152(13) O6 0.0340(14) 0.0536(16) 0.0440(15) 0.0079(12) 0.0207(12) 0.0013(12) C98 0.042(2) 0.055(2) 0.042(2) 0.0154(19) 0.0139(17) 0.0153(19) F4 0.084(2) 0.0817(19) 0.0719(18) 0.0519(16) 0.0437(16) 0.0379(16) F5 0.085(2) 0.0511(16) 0.079(2) 0.0117(14) 0.0335(17) 0.0243(15) F6 0.0605(18) 0.095(2) 0.079(2) 0.0404(18) -0.0012(15) 0.0317(16) S3 0.0417(5) 0.0300(4) 0.0508(5) 0.0197(4) 0.0255(4) 0.0130(4) O7 0.0446(15) 0.0327(13) 0.0507(15) 0.0162(12) 0.0139(12) 0.0135(11) O8 0.0365(14) 0.0336(13) 0.0671(18) 0.0125(13) 0.0184(13) 0.0119(11) O9 0.084(2) 0.0544(18) 0.081(2) 0.0454(17) 0.056(2) 0.0346(17) C99 0.041(2) 0.0331(19) 0.060(2) 0.0210(17) 0.0261(18) 0.0135(16) F7 0.0527(15) 0.0555(15) 0.089(2) 0.0233(14) 0.0333(14) 0.0293(12) F8 0.0620(16) 0.0310(11) 0.0797(18) 0.0096(11) 0.0379(14) 0.0085(11) F9 0.092(2) 0.0477(14) 0.0780(18) 0.0313(13) 0.0607(17) 0.0269(14) C81 0.044(3) 0.040(3) 0.054(3) 0.023(2) 0.022(2) 0.012(2) Cl1 0.0503(8) 0.0408(7) 0.0516(8) 0.0242(6) 0.0145(6) 0.0031(5) Cl2 0.0710(11) 0.0537(9) 0.0733(11) 0.0351(8) 0.0435(8) 0.0170(7) C82 0.051(2) 0.060(3) 0.047(2) 0.025(2) 0.0210(19) 0.025(2) Cl3 0.0784(8) 0.0495(6) 0.0931(9) 0.0201(6) 0.0592(7) 0.0132(6) Cl4 0.0953(10) 0.0691(8) 0.0907(9) 0.0506(7) 0.0593(8) 0.0453(7) Cl5 0.0716(8) 0.1068(10) 0.0455(6) 0.0247(6) 0.0299(6) 0.0423(7) Cl6 0.0431(8) 0.0439(8) 0.0498(9) 0.0236(6) 0.0132(6) 0.0124(6) Cl7 0.0405(10) 0.0783(16) 0.156(2) 0.0365(15) 0.0049(12) 0.0179(10) Cl8 0.224(4) 0.0765(15) 0.0430(11) 0.0100(9) 0.0279(15) 0.074(2) _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 N2 C3 1.362(5) . ? N2 C8 1.430(4) . ? N1 C1 1.314(4) . ? N1 C8 1.492(4) . ? N1 C11 1.495(4) . ? C1 C2 1.443(5) . ? C1 C9 1.494(4) . ? C2 C7 1.404(5) . ? C2 C3 1.416(4) . ? C3 C4 1.402(5) . ? C4 C5 1.374(6) . ? C5 C6 1.408(5) . ? C6 C7 1.373(5) . ? C8 C24 1.534(4) . ? C11 C16 1.525(4) . ? C11 C12 1.534(4) . ? C12 C13 1.526(5) . ? C13 C14 1.512(5) . ? C14 C15 1.533(5) . ? C15 C16 1.520(5) . ? N1' C1' 1.315(4) . ? N1' C8' 1.489(4) . ? N1' C61' 1.494(4) . ? N2' C3' 1.345(5) . ? N2' C8' 1.438(4) . ? C1' C2' 1.448(5) . ? C1' C9' 1.502(4) . ? C2' C7' 1.408(5) . ? C2' C3' 1.415(5) . ? C3' C4' 1.415(5) . ? C4' C5' 1.373(7) . ? C5' C6' 1.385(7) . ? C6' C7' 1.382(6) . ? C8' C34 1.535(4) . ? N1" C1" 1.307(5) . ? N1" C8" 1.482(4) . ? N1" C71 1.509(4) . ? N2" C3" 1.343(4) . ? N2" C8" 1.435(4) . ? C1" C2" 1.448(5) . ? C1" C9" 1.498(5) . ? C2" C3" 1.412(5) . ? C2" C7" 1.415(5) . ? C3" C4" 1.412(4) . ? C4" C5" 1.361(6) . ? C5" C6" 1.382(6) . ? C6" C7" 1.378(6) . ? C8" C44 1.543(4) . ? C101 C106 1.391(4) . ? C101 C102 1.405(4) . ? C101 C21 1.490(4) . ? C102 C103 1.387(4) . ? C103 C104 1.398(4) . ? C103 C31 1.497(4) . ? C104 C105 1.394(4) . ? C105 C106 1.398(4) . ? C105 C41 1.492(4) . ? C21 C22 1.396(4) . ? C21 C26 1.397(4) . ? C22 C23 1.388(4) . ? C23 C24 1.382(4) . ? C24 C25 1.391(4) . ? C25 C26 1.383(4) . ? C31 C32 1.394(4) . ? C31 C36 1.400(4) . ? C32 C33 1.395(4) . ? C33 C34 1.391(4) . ? C34 C35 1.383(4) . ? C35 C36 1.395(4) . ? C41 C42 1.392(4) . ? C41 C46 1.401(4) . ? C42 C43 1.398(4) . ? C43 C44 1.392(4) . ? C44 C45 1.389(4) . ? C45 C46 1.382(4) . ? C61' C66' 1.523(4) . ? C61' C62' 1.528(5) . ? C62' C63' 1.520(5) . ? C63' C64' 1.527(5) . ? C64' C65' 1.524(5) . ? C65' C66' 1.542(5) . ? C71 C76 1.525(5) . ? C71 C72 1.529(5) . ? C72 C73 1.525(5) . ? C73 C74 1.522(5) . ? C74 C75 1.509(6) . ? C75 C76 1.527(5) . ? S1 O1 1.437(2) . ? S1 O2 1.438(2) . ? S1 O3 1.439(2) . ? S1 C97 1.821(4) . ? C97 F3 1.340(4) . ? C97 F1 1.341(5) . ? C97 F2 1.342(4) . ? S2 O6 1.430(3) . ? S2 O5 1.436(3) . ? S2 O4 1.441(3) . ? S2 C98 1.811(5) . ? C98 F5 1.321(5) . ? C98 F6 1.324(5) . ? C98 F4 1.344(5) . ? S3 O9 1.421(3) . ? S3 O7 1.440(3) . ? S3 O8 1.442(3) . ? S3 C99 1.827(4) . ? C99 F7 1.320(5) . ? C99 F9 1.325(5) . ? C99 F8 1.326(5) . ? C81 Cl1 1.757(5) . ? C81 Cl2 1.759(5) . ? C81' Cl1' 1.740(16) . ? C81' Cl2' 1.751(16) . ? C82 Cl3 1.740(5) . ? C82 Cl4 1.743(5) . ? C82 Cl5 1.744(5) . ? C83 Cl7 1.729(6) . ? C83 Cl6 1.741(6) . ? C83 Cl8 1.766(7) . ? C83' Cl8' 1.738(15) . ? C83' Cl6' 1.751(15) . ? C83' Cl7' 1.761(15) . ? 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 C3 N2 C8 118.2(3) . . ? C1 N1 C8 118.2(3) . . ? C1 N1 C11 124.6(2) . . ? C8 N1 C11 117.1(2) . . ? N1 C1 C2 119.6(3) . . ? N1 C1 C9 121.5(3) . . ? C2 C1 C9 118.6(3) . . ? C7 C2 C3 119.1(3) . . ? C7 C2 C1 122.6(3) . . ? C3 C2 C1 117.6(3) . . ? N2 C3 C4 123.4(3) . . ? N2 C3 C2 116.8(3) . . ? C4 C3 C2 119.7(3) . . ? C5 C4 C3 119.4(3) . . ? C4 C5 C6 121.4(3) . . ? C7 C6 C5 119.3(4) . . ? C6 C7 C2 120.8(3) . . ? N2 C8 N1 109.3(2) . . ? N2 C8 C24 112.3(3) . . ? N1 C8 C24 111.8(2) . . ? N1 C11 C16 110.0(2) . . ? N1 C11 C12 112.2(2) . . ? C16 C11 C12 111.2(3) . . ? C13 C12 C11 108.7(3) . . ? C14 C13 C12 110.8(3) . . ? C13 C14 C15 111.0(3) . . ? C16 C15 C14 111.6(3) . . ? C15 C16 C11 110.4(3) . . ? C1' N1' C8' 119.7(3) . . ? C1' N1' C61' 123.9(2) . . ? C8' N1' C61' 116.4(2) . . ? C3' N2' C8' 120.0(3) . . ? N1' C1' C2' 119.4(3) . . ? N1' C1' C9' 120.8(3) . . ? C2' C1' C9' 119.7(3) . . ? C7' C2' C3' 119.1(3) . . ? C7' C2' C1' 122.1(3) . . ? C3' C2' C1' 117.9(3) . . ? N2' C3' C2' 118.4(3) . . ? N2' C3' C4' 121.9(3) . . ? C2' C3' C4' 119.6(4) . . ? C5' C4' C3' 119.2(4) . . ? C4' C5' C6' 121.6(4) . . ? C7' C6' C5' 120.3(4) . . ? C6' C7' C2' 120.0(4) . . ? N2' C8' N1' 109.6(2) . . ? N2' C8' C34 113.8(3) . . ? N1' C8' C34 111.0(2) . . ? C1" N1" C8" 118.5(3) . . ? C1" N1" C71 125.2(3) . . ? C8" N1" C71 116.2(3) . . ? C3" N2" C8" 118.7(3) . . ? N1" C1" C2" 119.6(3) . . ? N1" C1" C9" 120.7(3) . . ? C2" C1" C9" 119.4(3) . . ? C3" C2" C7" 118.4(3) . . ? C3" C2" C1" 117.2(3) . . ? C7" C2" C1" 123.5(3) . . ? N2" C3" C4" 122.9(3) . . ? N2" C3" C2" 117.4(3) . . ? C4" C3" C2" 119.6(3) . . ? C5" C4" C3" 119.7(3) . . ? C4" C5" C6" 121.5(3) . . ? C7" C6" C5" 120.1(4) . . ? C6" C7" C2" 120.3(4) . . ? N2" C8" N1" 108.7(2) . . ? N2" C8" C44 113.3(2) . . ? N1" C8" C44 111.7(2) . . ? C106 C101 C102 118.7(2) . . ? C106 C101 C21 120.2(2) . . ? C102 C101 C21 121.0(2) . . ? C103 C102 C101 121.1(2) . . ? C102 C103 C104 119.1(2) . . ? C102 C103 C31 119.9(2) . . ? C104 C103 C31 120.9(2) . . ? C105 C104 C103 121.1(2) . . ? C104 C105 C106 118.8(2) . . ? C104 C105 C41 120.8(2) . . ? C106 C105 C41 120.3(2) . . ? C101 C106 C105 121.3(2) . . ? C22 C21 C26 117.9(3) . . ? C22 C21 C101 121.6(3) . . ? C26 C21 C101 120.3(2) . . ? C23 C22 C21 121.4(3) . . ? C24 C23 C22 120.1(3) . . ? C23 C24 C25 119.1(3) . . ? C23 C24 C8 125.3(3) . . ? C25 C24 C8 115.5(3) . . ? C26 C25 C24 120.9(3) . . ? C25 C26 C21 120.6(3) . . ? C32 C31 C36 118.3(2) . . ? C32 C31 C103 121.8(2) . . ? C36 C31 C103 119.8(2) . . ? C31 C32 C33 120.7(3) . . ? C34 C33 C32 120.7(3) . . ? C35 C34 C33 118.9(3) . . ? C35 C34 C8' 116.4(2) . . ? C33 C34 C8' 124.7(3) . . ? C34 C35 C36 120.8(3) . . ? C35 C36 C31 120.6(3) . . ? C42 C41 C46 118.0(2) . . ? C42 C41 C105 121.2(3) . . ? C46 C41 C105 120.8(3) . . ? C41 C42 C43 121.3(3) . . ? C44 C43 C42 119.9(3) . . ? C45 C44 C43 119.0(3) . . ? C45 C44 C8" 116.3(3) . . ? C43 C44 C8" 124.7(3) . . ? C46 C45 C44 121.0(3) . . ? C45 C46 C41 120.8(3) . . ? N1' C61' C66' 109.0(2) . . ? N1' C61' C62' 112.2(2) . . ? C66' C61' C62' 111.7(3) . . ? C63' C62' C61' 108.8(3) . . ? C62' C63' C64' 111.0(3) . . ? C65' C64' C63' 110.5(3) . . ? C64' C65' C66' 110.8(3) . . ? C61' C66' C65' 110.9(3) . . ? N1" C71 C76 109.2(2) . . ? N1" C71 C72 111.2(2) . . ? C76 C71 C72 112.3(3) . . ? C73 C72 C71 110.8(3) . . ? C74 C73 C72 110.6(3) . . ? C75 C74 C73 110.1(3) . . ? C74 C75 C76 112.1(3) . . ? C71 C76 C75 111.6(3) . . ? O1 S1 O2 115.11(16) . . ? O1 S1 O3 115.77(15) . . ? O2 S1 O3 115.05(15) . . ? O1 S1 C97 101.61(17) . . ? O2 S1 C97 103.66(16) . . ? O3 S1 C97 102.84(18) . . ? F3 C97 F1 107.1(3) . . ? F3 C97 F2 107.5(3) . . ? F1 C97 F2 107.3(3) . . ? F3 C97 S1 112.3(3) . . ? F1 C97 S1 111.7(3) . . ? F2 C97 S1 110.7(3) . . ? O6 S2 O5 115.55(17) . . ? O6 S2 O4 115.87(17) . . ? O5 S2 O4 113.44(19) . . ? O6 S2 C98 103.7(2) . . ? O5 S2 C98 103.59(19) . . ? O4 S2 C98 102.29(19) . . ? F5 C98 F6 108.2(4) . . ? F5 C98 F4 106.9(4) . . ? F6 C98 F4 107.3(4) . . ? F5 C98 S2 111.0(3) . . ? F6 C98 S2 112.1(3) . . ? F4 C98 S2 111.1(3) . . ? O9 S3 O7 115.8(2) . . ? O9 S3 O8 114.8(2) . . ? O7 S3 O8 114.37(16) . . ? O9 S3 C99 102.59(18) . . ? O7 S3 C99 103.24(17) . . ? O8 S3 C99 103.53(19) . . ? F7 C99 F9 107.4(3) . . ? F7 C99 F8 108.4(3) . . ? F9 C99 F8 107.4(4) . . ? F7 C99 S3 110.8(3) . . ? F9 C99 S3 111.3(3) . . ? F8 C99 S3 111.4(3) . . ? Cl1 C81 Cl2 113.4(3) . . ? Cl1' C81' Cl2' 107.3(16) . . ? Cl3 C82 Cl4 112.1(2) . . ? Cl3 C82 Cl5 110.9(3) . . ? Cl4 C82 Cl5 110.6(3) . . ? Cl7 C83 Cl6 109.5(4) . . ? Cl7 C83 Cl8 107.6(4) . . ? Cl6 C83 Cl8 110.9(3) . . ? Cl8' C83' Cl6' 116.4(19) . . ? Cl8' C83' Cl7' 92.6(14) . . ? Cl6' C83' Cl7' 107.8(15) . . ? 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 C8 N1 C1 C2 -2.3(4) . . . . ? C11 N1 C1 C2 175.0(3) . . . . ? C8 N1 C1 C9 -176.5(3) . . . . ? C11 N1 C1 C9 0.9(4) . . . . ? N1 C1 C2 C7 165.6(3) . . . . ? C9 C1 C2 C7 -20.1(4) . . . . ? N1 C1 C2 C3 -24.5(4) . . . . ? C9 C1 C2 C3 149.8(3) . . . . ? C8 N2 C3 C4 -158.2(3) . . . . ? C8 N2 C3 C2 25.5(4) . . . . ? C7 C2 C3 N2 -176.9(3) . . . . ? C1 C2 C3 N2 12.8(4) . . . . ? C7 C2 C3 C4 6.6(4) . . . . ? C1 C2 C3 C4 -163.7(3) . . . . ? N2 C3 C4 C5 176.8(3) . . . . ? C2 C3 C4 C5 -6.9(5) . . . . ? C3 C4 C5 C6 2.3(5) . . . . ? C4 C5 C6 C7 2.8(5) . . . . ? C5 C6 C7 C2 -3.1(5) . . . . ? C3 C2 C7 C6 -1.5(5) . . . . ? C1 C2 C7 C6 168.2(3) . . . . ? C3 N2 C8 N1 -49.7(4) . . . . ? C3 N2 C8 C24 75.0(3) . . . . ? C1 N1 C8 N2 37.4(4) . . . . ? C11 N1 C8 N2 -140.2(3) . . . . ? C1 N1 C8 C24 -87.6(3) . . . . ? C11 N1 C8 C24 94.9(3) . . . . ? C1 N1 C11 C16 -91.9(3) . . . . ? C8 N1 C11 C16 85.5(3) . . . . ? C1 N1 C11 C12 143.8(3) . . . . ? C8 N1 C11 C12 -38.8(3) . . . . ? N1 C11 C12 C13 -177.2(3) . . . . ? C16 C11 C12 C13 59.2(3) . . . . ? C11 C12 C13 C14 -59.3(4) . . . . ? C12 C13 C14 C15 57.6(4) . . . . ? C13 C14 C15 C16 -54.9(4) . . . . ? C14 C15 C16 C11 54.3(4) . . . . ? N1 C11 C16 C15 178.0(2) . . . . ? C12 C11 C16 C15 -57.1(3) . . . . ? C8' N1' C1' C2' -9.1(4) . . . . ? C61' N1' C1' C2' 169.1(3) . . . . ? C8' N1' C1' C9' 173.9(3) . . . . ? C61' N1' C1' C9' -8.0(4) . . . . ? N1' C1' C2' C7' 174.2(3) . . . . ? C9' C1' C2' C7' -8.7(5) . . . . ? N1' C1' C2' C3' -16.6(4) . . . . ? C9' C1' C2' C3' 160.5(3) . . . . ? C8' N2' C3' C2' 19.8(4) . . . . ? C8' N2' C3' C4' -164.0(3) . . . . ? C7' C2' C3' N2' -179.0(3) . . . . ? C1' C2' C3' N2' 11.5(4) . . . . ? C7' C2' C3' C4' 4.7(5) . . . . ? C1' C2' C3' C4' -164.8(3) . . . . ? N2' C3' C4' C5' 179.5(4) . . . . ? C2' C3' C4' C5' -4.4(5) . . . . ? C3' C4' C5' C6' 0.6(7) . . . . ? C4' C5' C6' C7' 2.8(8) . . . . ? C5' C6' C7' C2' -2.4(7) . . . . ? C3' C2' C7' C6' -1.4(6) . . . . ? C1' C2' C7' C6' 167.7(4) . . . . ? C3' N2' C8' N1' -42.5(4) . . . . ? C3' N2' C8' C34 82.4(3) . . . . ? C1' N1' C8' N2' 36.9(3) . . . . ? C61' N1' C8' N2' -141.4(3) . . . . ? C1' N1' C8' C34 -89.6(3) . . . . ? C61' N1' C8' C34 92.1(3) . . . . ? C8" N1" C1" C2" -5.4(4) . . . . ? C71 N1" C1" C2" 171.5(3) . . . . ? C8" N1" C1" C9" -179.0(3) . . . . ? C71 N1" C1" C9" -2.2(5) . . . . ? N1" C1" C2" C3" -22.3(4) . . . . ? C9" C1" C2" C3" 151.4(3) . . . . ? N1" C1" C2" C7" 168.5(3) . . . . ? C9" C1" C2" C7" -17.8(5) . . . . ? C8" N2" C3" C4" -159.4(3) . . . . ? C8" N2" C3" C2" 24.2(4) . . . . ? C7" C2" C3" N2" -177.3(3) . . . . ? C1" C2" C3" N2" 12.9(4) . . . . ? C7" C2" C3" C4" 6.1(5) . . . . ? C1" C2" C3" C4" -163.7(3) . . . . ? N2" C3" C4" C5" 177.1(3) . . . . ? C2" C3" C4" C5" -6.5(5) . . . . ? C3" C4" C5" C6" 1.9(6) . . . . ? C4" C5" C6" C7" 3.0(6) . . . . ? C5" C6" C7" C2" -3.3(6) . . . . ? C3" C2" C7" C6" -1.2(5) . . . . ? C1" C2" C7" C6" 167.9(4) . . . . ? C3" N2" C8" N1" -49.1(3) . . . . ? C3" N2" C8" C44 75.7(3) . . . . ? C1" N1" C8" N2" 38.9(4) . . . . ? C71 N1" C8" N2" -138.2(3) . . . . ? C1" N1" C8" C44 -86.8(3) . . . . ? C71 N1" C8" C44 96.1(3) . . . . ? C106 C101 C102 C103 -0.6(5) . . . . ? C21 C101 C102 C103 174.9(3) . . . . ? C101 C102 C103 C104 0.7(4) . . . . ? C101 C102 C103 C31 -175.5(3) . . . . ? C102 C103 C104 C105 -0.5(4) . . . . ? C31 C103 C104 C105 175.6(3) . . . . ? C103 C104 C105 C106 0.3(4) . . . . ? C103 C104 C105 C41 -175.5(3) . . . . ? C102 C101 C106 C105 0.4(4) . . . . ? C21 C101 C106 C105 -175.2(3) . . . . ? C104 C105 C106 C101 -0.2(4) . . . . ? C41 C105 C106 C101 175.6(3) . . . . ? C106 C101 C21 C22 -31.7(4) . . . . ? C102 C101 C21 C22 152.8(3) . . . . ? C106 C101 C21 C26 143.2(3) . . . . ? C102 C101 C21 C26 -32.2(4) . . . . ? C26 C21 C22 C23 -1.6(4) . . . . ? C101 C21 C22 C23 173.4(3) . . . . ? C21 C22 C23 C24 1.0(5) . . . . ? C22 C23 C24 C25 -0.1(5) . . . . ? C22 C23 C24 C8 -179.7(3) . . . . ? N2 C8 C24 C23 -103.6(3) . . . . ? N1 C8 C24 C23 19.7(4) . . . . ? N2 C8 C24 C25 76.8(3) . . . . ? N1 C8 C24 C25 -160.0(3) . . . . ? C23 C24 C25 C26 -0.3(5) . . . . ? C8 C24 C25 C26 179.4(3) . . . . ? C24 C25 C26 C21 -0.4(5) . . . . ? C22 C21 C26 C25 1.3(4) . . . . ? C101 C21 C26 C25 -173.8(3) . . . . ? C102 C103 C31 C32 -36.9(4) . . . . ? C104 C103 C31 C32 147.0(3) . . . . ? C102 C103 C31 C36 139.2(3) . . . . ? C104 C103 C31 C36 -36.9(4) . . . . ? C36 C31 C32 C33 -1.4(5) . . . . ? C103 C31 C32 C33 174.8(3) . . . . ? C31 C32 C33 C34 -0.3(5) . . . . ? C32 C33 C34 C35 1.4(5) . . . . ? C32 C33 C34 C8' -176.3(3) . . . . ? N2' C8' C34 C35 82.6(4) . . . . ? N1' C8' C34 C35 -153.2(3) . . . . ? N2' C8' C34 C33 -99.6(4) . . . . ? N1' C8' C34 C33 24.5(4) . . . . ? C33 C34 C35 C36 -0.8(5) . . . . ? C8' C34 C35 C36 177.1(3) . . . . ? C34 C35 C36 C31 -0.8(5) . . . . ? C32 C31 C36 C35 1.9(5) . . . . ? C103 C31 C36 C35 -174.3(3) . . . . ? C104 C105 C41 C42 -33.5(4) . . . . ? C106 C105 C41 C42 150.8(3) . . . . ? C104 C105 C41 C46 143.7(3) . . . . ? C106 C105 C41 C46 -32.0(4) . . . . ? C46 C41 C42 C43 -1.0(4) . . . . ? C105 C41 C42 C43 176.3(3) . . . . ? C41 C42 C43 C44 0.2(5) . . . . ? C42 C43 C44 C45 0.7(4) . . . . ? C42 C43 C44 C8" -177.8(3) . . . . ? N2" C8" C44 C45 67.5(4) . . . . ? N1" C8" C44 C45 -169.4(3) . . . . ? N2" C8" C44 C43 -114.0(3) . . . . ? N1" C8" C44 C43 9.1(4) . . . . ? C43 C44 C45 C46 -0.6(4) . . . . ? C8" C44 C45 C46 177.9(3) . . . . ? C44 C45 C46 C41 -0.2(4) . . . . ? C42 C41 C46 C45 1.1(4) . . . . ? C105 C41 C46 C45 -176.3(3) . . . . ? C1' N1' C61' C66' -95.2(3) . . . . ? C8' N1' C61' C66' 83.0(3) . . . . ? C1' N1' C61' C62' 140.5(3) . . . . ? C8' N1' C61' C62' -41.3(3) . . . . ? N1' C61' C62' C63' -179.2(3) . . . . ? C66' C61' C62' C63' 58.1(4) . . . . ? C61' C62' C63' C64' -59.5(4) . . . . ? C62' C63' C64' C65' 59.1(4) . . . . ? C63' C64' C65' C66' -55.5(4) . . . . ? N1' C61' C66' C65' 179.6(2) . . . . ? C62' C61' C66' C65' -55.8(3) . . . . ? C64' C65' C66' C61' 54.0(4) . . . . ? C1" N1" C71 C76 -98.6(4) . . . . ? C8" N1" C71 C76 78.3(3) . . . . ? C1" N1" C71 C72 136.8(3) . . . . ? C8" N1" C71 C72 -46.2(3) . . . . ? N1" C71 C72 C73 176.1(3) . . . . ? C76 C71 C72 C73 53.3(4) . . . . ? C71 C72 C73 C74 -57.2(4) . . . . ? C72 C73 C74 C75 59.1(4) . . . . ? C73 C74 C75 C76 -57.2(4) . . . . ? N1" C71 C76 C75 -174.9(3) . . . . ? C72 C71 C76 C75 -51.1(4) . . . . ? C74 C75 C76 C71 53.3(4) . . . . ? O1 S1 C97 F3 179.8(3) . . . . ? O2 S1 C97 F3 60.1(3) . . . . ? O3 S1 C97 F3 -60.1(3) . . . . ? O1 S1 C97 F1 59.5(3) . . . . ? O2 S1 C97 F1 -60.3(3) . . . . ? O3 S1 C97 F1 179.6(2) . . . . ? O1 S1 C97 F2 -60.1(3) . . . . ? O2 S1 C97 F2 -179.8(2) . . . . ? O3 S1 C97 F2 60.1(3) . . . . ? O6 S2 C98 F5 64.0(3) . . . . ? O5 S2 C98 F5 -175.0(3) . . . . ? O4 S2 C98 F5 -56.8(3) . . . . ? O6 S2 C98 F6 -57.1(4) . . . . ? O5 S2 C98 F6 63.9(4) . . . . ? O4 S2 C98 F6 -177.9(3) . . . . ? O6 S2 C98 F4 -177.2(3) . . . . ? O5 S2 C98 F4 -56.1(3) . . . . ? O4 S2 C98 F4 62.0(3) . . . . ? O9 S3 C99 F7 -59.9(3) . . . . ? O7 S3 C99 F7 60.8(3) . . . . ? O8 S3 C99 F7 -179.7(3) . . . . ? O9 S3 C99 F9 -179.4(3) . . . . ? O7 S3 C99 F9 -58.7(3) . . . . ? O8 S3 C99 F9 60.8(3) . . . . ? O9 S3 C99 F8 60.8(3) . . . . ? O7 S3 C99 F8 -178.5(3) . . . . ? O8 S3 C99 F8 -59.0(3) . . . . ? 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 N2 H02 O8 0.84(3) 2.18(3) 2.930(4) 148(4) . N2' H02' O3 0.84(3) 2.31(3) 3.066(3) 150(4) . N2" H02" O6 0.83(3) 2.38(3) 3.023(4) 135(3) . N2" H02" O4 0.83(3) 2.50(3) 3.171(4) 139(3) 2_776 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 72.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.115 _refine_diff_density_min -1.195 _refine_diff_density_rms 0.085 # Attachment '7d2.cif' data_ajf44bs _database_code_depnum_ccdc_archive 'CCDC 800057' #TrackingRef '7d2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 Cl3 F3 N2 O3 S' _chemical_formula_weight 587.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.8166(17) _cell_length_b 16.328(2) _cell_length_c 13.928(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.356(3) _cell_angle_gamma 90.00 _cell_volume 2625.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3361 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 24.19 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.480 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8720 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31789 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_sigmaI/netI 0.0638 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.75 _reflns_number_total 6412 _reflns_number_gt 4900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The chrloroform solvent is disordered over two positions, ca 65:35%. ; _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^)+(0.0365P)^2^+5.3236P] 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 'NH free wtih DFIX, rigid methyl other riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6412 _refine_ls_number_parameters 350 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.1243 _refine_ls_R_factor_gt 0.0959 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1528 _refine_ls_goodness_of_fit_ref 1.242 _refine_ls_restrained_S_all 1.262 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4304(3) 0.4906(2) 0.2609(2) 0.0182(7) Uani 1 1 d . . . H01 H 0.424(4) 0.536(3) 0.279(3) 0.022 Uiso 1 1 d . . . C1 C 0.5040(3) 0.4426(2) 0.3168(3) 0.0151(7) Uani 1 1 d . . . C2 C 0.5798(3) 0.4720(2) 0.4052(3) 0.0157(7) Uani 1 1 d . . . C3 C 0.6517(3) 0.4146(2) 0.4662(3) 0.0152(7) Uani 1 1 d . . . N2 N 0.6448(3) 0.3332(2) 0.4479(2) 0.0199(7) Uani 1 1 d D . . H02 H 0.678(3) 0.302(2) 0.493(2) 0.024(12) Uiso 1 1 d D . . C4 C 0.7352(3) 0.4441(2) 0.5471(3) 0.0204(8) Uani 1 1 d . . . H4 H 0.7847 0.4068 0.5885 0.024 Uiso 1 1 calc R . . C5 C 0.7450(3) 0.5263(2) 0.5659(3) 0.0209(8) Uani 1 1 d . . . H5 H 0.8017 0.5451 0.6204 0.025 Uiso 1 1 calc R . . C6 C 0.6735(3) 0.5835(2) 0.5069(3) 0.0190(8) Uani 1 1 d . . . H6 H 0.6811 0.6403 0.5215 0.023 Uiso 1 1 calc R . . C7 C 0.5929(3) 0.5563(2) 0.4282(3) 0.0169(7) Uani 1 1 d . . . H7 H 0.5445 0.5949 0.3879 0.020 Uiso 1 1 calc R . . C8 C 0.5175(3) 0.3556(2) 0.2878(3) 0.0165(7) Uani 1 1 d . . . H8A H 0.5784 0.3526 0.2489 0.020 Uiso 1 1 calc R . . H8B H 0.4440 0.3368 0.2453 0.020 Uiso 1 1 calc R . . C9 C 0.5497(3) 0.2979(2) 0.3761(3) 0.0184(8) Uani 1 1 d . . . H9 H 0.4812 0.2911 0.4069 0.022 Uiso 1 1 calc R . . C11 C 0.3584(3) 0.4747(2) 0.1624(3) 0.0173(8) Uani 1 1 d . . . H11 H 0.3705 0.4169 0.1430 0.021 Uiso 1 1 calc R . . C12 C 0.3961(3) 0.5330(3) 0.0894(3) 0.0211(8) Uani 1 1 d . . . H12A H 0.3935 0.5901 0.1128 0.025 Uiso 1 1 calc R . . H12B H 0.4769 0.5205 0.0853 0.025 Uiso 1 1 calc R . . C13 C 0.3173(3) 0.5245(3) -0.0119(3) 0.0222(8) Uani 1 1 d . . . H13A H 0.3250 0.4687 -0.0376 0.027 Uiso 1 1 calc R . . H13B H 0.3412 0.5642 -0.0575 0.027 Uiso 1 1 calc R . . C14 C 0.1911(3) 0.5400(2) -0.0075(3) 0.0202(8) Uani 1 1 d . . . H14A H 0.1822 0.5968 0.0146 0.024 Uiso 1 1 calc R . . H14B H 0.1411 0.5333 -0.0738 0.024 Uiso 1 1 calc R . . C15 C 0.1541(3) 0.4798(3) 0.0635(3) 0.0219(8) Uani 1 1 d . . . H15A H 0.1582 0.4233 0.0387 0.026 Uiso 1 1 calc R . . H15B H 0.0727 0.4909 0.0671 0.026 Uiso 1 1 calc R . . C16 C 0.2314(3) 0.4868(2) 0.1660(3) 0.0184(8) Uani 1 1 d . . . H16A H 0.2212 0.5415 0.1938 0.022 Uiso 1 1 calc R . . H16B H 0.2084 0.4450 0.2096 0.022 Uiso 1 1 calc R . . C21 C 0.5825(3) 0.2154(2) 0.3406(3) 0.0170(8) Uani 1 1 d . . . C22 C 0.6943(3) 0.2009(2) 0.3267(3) 0.0240(9) Uani 1 1 d . . . H22 H 0.7524 0.2416 0.3452 0.029 Uiso 1 1 calc R . . C23 C 0.7212(3) 0.1279(2) 0.2864(3) 0.0247(9) Uani 1 1 d . . . H23 H 0.7981 0.1189 0.2787 0.030 Uiso 1 1 calc R . . C24 C 0.6386(3) 0.0676(2) 0.2570(3) 0.0207(8) Uani 1 1 d . . . C25 C 0.5274(3) 0.0827(2) 0.2716(3) 0.0220(8) Uani 1 1 d . . . H25 H 0.4692 0.0422 0.2528 0.026 Uiso 1 1 calc R . . C26 C 0.4993(3) 0.1549(2) 0.3127(3) 0.0209(8) Uani 1 1 d . . . H26 H 0.4228 0.1632 0.3220 0.025 Uiso 1 1 calc R . . C27 C 0.6684(4) -0.0107(3) 0.2106(3) 0.0309(10) Uani 1 1 d . . . H27A H 0.6865 0.0015 0.1467 0.046 Uiso 1 1 calc R . . H27B H 0.6023 -0.0483 0.2016 0.046 Uiso 1 1 calc R . . H27C H 0.7358 -0.0362 0.2535 0.046 Uiso 1 1 calc R . . C98 C 0.5611(5) 0.2368(4) -0.0060(5) 0.0262(18) Uani 0.653(10) 1 d PD A 1 H98 H 0.5763 0.2455 -0.0732 0.031 Uiso 0.653(10) 1 calc PR A 1 Cl1 Cl 0.6875(2) 0.25964(16) 0.0723(3) 0.0362(7) Uani 0.653(10) 1 d PD A 1 Cl2 Cl 0.5130(3) 0.13510(18) -0.0055(3) 0.0309(9) Uani 0.653(10) 1 d PD A 1 Cl3 Cl 0.4510(2) 0.3077(2) 0.0040(3) 0.0338(7) Uani 0.653(10) 1 d PD A 1 C98' C 0.5397(7) 0.2190(6) 0.0649(8) 0.020(3) Uiso 0.347(10) 1 d PD A 2 H98' H 0.5222 0.2023 0.1293 0.024 Uiso 0.347(10) 1 calc PR A 2 Cl1' Cl 0.6747(5) 0.2475(4) 0.0943(4) 0.0274(13) Uiso 0.347(10) 1 d PD A 2 Cl2' Cl 0.5109(10) 0.1316(6) -0.0057(11) 0.088(4) Uiso 0.347(10) 1 d PD A 2 Cl3' Cl 0.4371(6) 0.2923(4) 0.0225(5) 0.0372(18) Uiso 0.347(10) 1 d PD A 2 C99 C 0.0200(3) 0.2854(2) 0.1874(3) 0.0238(9) Uani 1 1 d . . . F1 F -0.0330(2) 0.26630(17) 0.0959(2) 0.0407(7) Uani 1 1 d . . . F2 F -0.0446(2) 0.25606(17) 0.2465(2) 0.0458(7) Uani 1 1 d . . . F3 F 0.0209(2) 0.36658(14) 0.1956(2) 0.0368(7) Uani 1 1 d . . . S1 S 0.16639(8) 0.24280(6) 0.21706(7) 0.0179(2) Uani 1 1 d . . . O1 O 0.2138(3) 0.2753(2) 0.3129(2) 0.0446(9) Uani 1 1 d . . . O2 O 0.1436(3) 0.15581(16) 0.2138(2) 0.0302(7) Uani 1 1 d . . . O3 O 0.2182(2) 0.27181(17) 0.1396(2) 0.0279(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0196(15) 0.0136(16) 0.0194(17) -0.0030(13) -0.0001(13) 0.0038(13) C1 0.0116(16) 0.0177(18) 0.0177(18) 0.0018(14) 0.0069(14) -0.0017(14) C2 0.0131(16) 0.0204(19) 0.0139(17) -0.0015(14) 0.0034(14) -0.0020(14) C3 0.0136(16) 0.0213(19) 0.0111(17) 0.0014(14) 0.0033(13) -0.0007(14) N2 0.0224(17) 0.0175(16) 0.0154(16) 0.0048(13) -0.0058(13) 0.0052(13) C4 0.0165(18) 0.027(2) 0.0174(19) 0.0044(16) 0.0022(15) -0.0010(16) C5 0.0204(18) 0.028(2) 0.0147(18) -0.0017(16) 0.0042(15) -0.0044(16) C6 0.0191(18) 0.0205(19) 0.0191(19) -0.0044(16) 0.0080(15) -0.0061(15) C7 0.0157(17) 0.0157(18) 0.0196(19) 0.0013(15) 0.0044(14) 0.0023(14) C8 0.0184(18) 0.0151(18) 0.0141(18) -0.0002(14) -0.0008(14) 0.0013(14) C9 0.0191(18) 0.0177(19) 0.0178(19) -0.0009(15) 0.0023(15) 0.0010(15) C11 0.0185(18) 0.0151(18) 0.0147(18) -0.0023(14) -0.0045(14) 0.0049(14) C12 0.0150(17) 0.028(2) 0.020(2) 0.0009(16) 0.0030(15) 0.0015(16) C13 0.0232(19) 0.025(2) 0.0177(19) 0.0048(16) 0.0036(15) 0.0007(17) C14 0.0176(18) 0.023(2) 0.0169(19) 0.0018(15) -0.0025(15) 0.0036(16) C15 0.0165(18) 0.028(2) 0.019(2) 0.0033(16) -0.0028(15) -0.0037(16) C16 0.0160(17) 0.020(2) 0.0175(19) 0.0010(15) -0.0006(14) -0.0035(15) C21 0.0220(18) 0.0138(18) 0.0133(18) 0.0035(14) -0.0001(14) 0.0040(15) C22 0.0185(19) 0.024(2) 0.028(2) 0.0005(17) 0.0007(16) -0.0032(16) C23 0.0208(19) 0.025(2) 0.030(2) 0.0012(18) 0.0098(17) 0.0033(17) C24 0.027(2) 0.0185(19) 0.0167(19) 0.0039(15) 0.0062(16) 0.0010(16) C25 0.0200(19) 0.021(2) 0.024(2) 0.0008(16) 0.0021(16) -0.0024(16) C26 0.0184(18) 0.023(2) 0.021(2) 0.0037(16) 0.0040(15) 0.0033(15) C27 0.039(2) 0.024(2) 0.034(2) -0.0065(19) 0.017(2) -0.0001(19) C98 0.022(3) 0.027(4) 0.029(4) -0.003(3) 0.004(3) 0.000(3) Cl1 0.0214(10) 0.0283(11) 0.0610(17) 0.0130(11) 0.0135(10) -0.0010(7) Cl2 0.0274(11) 0.0173(10) 0.0501(16) -0.0084(7) 0.0132(8) -0.0069(6) Cl3 0.0179(10) 0.0313(13) 0.0483(16) 0.0007(13) -0.0017(10) 0.0095(9) C99 0.0207(19) 0.0156(19) 0.036(2) -0.0001(17) 0.0089(17) -0.0003(15) F1 0.0262(13) 0.0424(16) 0.0442(16) -0.0022(13) -0.0133(12) 0.0043(12) F2 0.0389(15) 0.0390(16) 0.069(2) 0.0060(15) 0.0324(14) -0.0041(13) F3 0.0282(13) 0.0178(13) 0.0657(19) -0.0009(12) 0.0132(13) 0.0053(10) S1 0.0184(4) 0.0136(4) 0.0195(5) -0.0014(4) -0.0011(3) 0.0005(4) O1 0.051(2) 0.042(2) 0.0303(18) -0.0119(15) -0.0144(15) 0.0045(16) O2 0.0332(16) 0.0143(14) 0.0421(18) 0.0023(13) 0.0060(14) -0.0010(12) O3 0.0250(15) 0.0207(15) 0.0407(18) 0.0009(13) 0.0131(13) -0.0017(12) _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 1.299(5) . ? N1 C11 1.475(5) . ? C1 C2 1.441(5) . ? C1 C8 1.494(5) . ? C2 C7 1.415(5) . ? C2 C3 1.418(5) . ? C3 N2 1.352(5) . ? C3 C4 1.415(5) . ? N2 C9 1.453(5) . ? C4 C5 1.367(6) . ? C5 C6 1.401(5) . ? C6 C7 1.363(5) . ? C8 C9 1.530(5) . ? C9 C21 1.515(5) . ? C11 C16 1.525(5) . ? C11 C12 1.526(5) . ? C12 C13 1.522(5) . ? C13 C14 1.526(5) . ? C14 C15 1.523(5) . ? C15 C16 1.526(5) . ? C21 C26 1.388(5) . ? C21 C22 1.396(5) . ? C22 C23 1.384(6) . ? C23 C24 1.384(5) . ? C24 C25 1.394(5) . ? C24 C27 1.508(5) . ? C25 C26 1.381(5) . ? C98 Cl1 1.692(6) . ? C98 Cl2 1.756(6) . ? C98 Cl3 1.770(6) . ? C98' Cl1' 1.627(9) . ? C98' Cl3' 1.717(9) . ? C98' Cl2' 1.725(11) . ? C99 F2 1.327(5) . ? C99 F3 1.330(4) . ? C99 F1 1.332(5) . ? C99 S1 1.828(4) . ? S1 O3 1.430(3) . ? S1 O1 1.434(3) . ? S1 O2 1.445(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C11 129.0(3) . . ? N1 C1 C2 121.6(3) . . ? N1 C1 C8 120.6(3) . . ? C2 C1 C8 117.7(3) . . ? C7 C2 C3 119.0(3) . . ? C7 C2 C1 122.4(3) . . ? C3 C2 C1 118.3(3) . . ? N2 C3 C4 119.2(3) . . ? N2 C3 C2 122.1(3) . . ? C4 C3 C2 118.6(3) . . ? C3 N2 C9 121.7(3) . . ? C5 C4 C3 120.2(4) . . ? C4 C5 C6 121.8(4) . . ? C7 C6 C5 118.9(4) . . ? C6 C7 C2 121.5(3) . . ? C1 C8 C9 113.0(3) . . ? N2 C9 C21 111.3(3) . . ? N2 C9 C8 109.4(3) . . ? C21 C9 C8 108.8(3) . . ? N1 C11 C16 108.8(3) . . ? N1 C11 C12 108.5(3) . . ? C16 C11 C12 111.8(3) . . ? C13 C12 C11 110.7(3) . . ? C12 C13 C14 110.9(3) . . ? C15 C14 C13 109.8(3) . . ? C14 C15 C16 111.2(3) . . ? C11 C16 C15 110.8(3) . . ? C26 C21 C22 118.4(3) . . ? C26 C21 C9 120.6(3) . . ? C22 C21 C9 120.7(3) . . ? C23 C22 C21 120.5(4) . . ? C22 C23 C24 121.6(4) . . ? C23 C24 C25 117.2(4) . . ? C23 C24 C27 121.0(4) . . ? C25 C24 C27 121.7(4) . . ? C26 C25 C24 121.9(4) . . ? C25 C26 C21 120.3(4) . . ? Cl1 C98 Cl2 116.6(4) . . ? Cl1 C98 Cl3 111.5(3) . . ? Cl2 C98 Cl3 111.9(3) . . ? Cl1' C98' Cl3' 118.0(6) . . ? Cl1' C98' Cl2' 116.3(7) . . ? Cl3' C98' Cl2' 110.0(6) . . ? F2 C99 F3 107.5(3) . . ? F2 C99 F1 107.1(3) . . ? F3 C99 F1 108.0(3) . . ? F2 C99 S1 111.4(3) . . ? F3 C99 S1 111.8(3) . . ? F1 C99 S1 110.9(3) . . ? O3 S1 O1 115.8(2) . . ? O3 S1 O2 114.17(18) . . ? O1 S1 O2 115.2(2) . . ? O3 S1 C99 103.94(18) . . ? O1 S1 C99 103.4(2) . . ? O2 S1 C99 101.89(18) . . ? 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 N1 H01 O2 0.79(4) 2.12(4) 2.880(4) 160(4) 2 C7 H7 O2 0.95 2.57 3.463(5) 157.6 2 N2 H02 O3 0.840(19) 2.33(2) 3.136(4) 161(4) 4_666 _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.720 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.086