# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Andrew J.P. White' _publ_contact_author_email a.white@imperial.ac.uk loop_ _publ_author_name 'Jean Levy' 'Christopher Latham' 'Loic Roisin' 'Nadine Kandziora' 'Di Fruscia, Paolo' 'Andrew White' S.Woodward 'Matthew Fuchter' data_15a _database_code_depnum_ccdc_archive 'CCDC 842971' #TrackingRef 'Org Lett 08-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H17 N2 O2, C F3 O3 S' _chemical_formula_sum 'C22 H17 F3 N2 O5 S' _chemical_formula_weight 478.44 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 10.02411(5) _cell_length_b 10.34453(6) _cell_length_c 20.23764(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2098.535(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 17461 _cell_measurement_theta_min 2.1808 _cell_measurement_theta_max 72.3253 _exptl_crystal_description blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 1.967 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.659 _exptl_absorpt_correction_T_max 0.843 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22029 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.37 _diffrn_reflns_theta_max 72.49 _reflns_number_total 4146 _reflns_number_gt 4004 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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. Results of chirality/polarity tests _refine_ls_R_factor_obs+ 0.0270 _refine_ls_wR_factor_obs+ 0.0700 _refine_ls_abs_structure_Flack+ 0.000(12) _refine_ls_R_factor_obs- 0.0428 _refine_ls_wR_factor_obs- 0.1145 _refine_ls_abs_structure_Flack- 1.003(12) ; _chemical_absolute_configuration ad _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^)+(0.0424P)^2^+0.3218P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 1774 Friedel pairs' _refine_ls_abs_structure_Flack -0.003(12) _refine_ls_number_reflns 4146 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0709 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.50174(15) 0.38853(14) 0.54324(7) 0.0317(3) Uani 1 1 d . . . H1A H 0.5124 0.3342 0.5058 0.038 Uiso 1 1 calc R . . N2 N 0.41141(12) 0.37758(11) 0.59144(6) 0.0305(2) Uani 1 1 d . . . C3 C 0.30032(13) 0.29193(14) 0.60837(7) 0.0312(3) Uani 1 1 d . . . H3A H 0.2324 0.2882 0.5722 0.037 Uiso 1 1 calc R . . C4 C 0.33932(14) 0.15945(14) 0.63137(7) 0.0315(3) Uani 1 1 d . . . C5 C 0.40052(15) 0.06267(15) 0.59507(8) 0.0377(3) Uani 1 1 d . . . H5A H 0.4286 0.0782 0.5509 0.045 Uiso 1 1 calc R . . C6 C 0.42008(17) -0.05690(17) 0.62410(10) 0.0445(4) Uani 1 1 d . . . H6A H 0.4608 -0.1246 0.5996 0.053 Uiso 1 1 calc R . . C7 C 0.38043(18) -0.07844(16) 0.68897(10) 0.0479(4) Uani 1 1 d . . . H7A H 0.3945 -0.1608 0.7085 0.058 Uiso 1 1 calc R . . C8 C 0.32067(19) 0.01888(17) 0.72540(9) 0.0454(4) Uani 1 1 d . . . H8A H 0.2935 0.0038 0.7697 0.054 Uiso 1 1 calc R . . C9 C 0.30085(15) 0.13933(16) 0.69619(8) 0.0362(3) Uani 1 1 d . . . C10 C 0.23690(19) 0.25840(17) 0.72551(8) 0.0453(4) Uani 1 1 d . . . H10A H 0.2860 0.2872 0.7653 0.054 Uiso 1 1 calc R . . H10B H 0.1430 0.2410 0.7378 0.054 Uiso 1 1 calc R . . C11 C 0.24432(15) 0.36031(15) 0.67129(7) 0.0357(3) Uani 1 1 d . . . H11A H 0.1541 0.3977 0.6624 0.043 Uiso 1 1 calc R . . O12 O 0.34034(12) 0.46309(11) 0.68843(6) 0.0425(3) Uani 1 1 d . . . C13 C 0.42669(15) 0.47329(14) 0.63809(7) 0.0333(3) Uani 1 1 d . . . C14 C 0.52893(15) 0.54800(13) 0.61671(8) 0.0332(3) Uani 1 1 d . . . O15 O 0.59531(11) 0.65757(10) 0.63170(6) 0.0403(2) Uani 1 1 d . . . C16 C 0.71305(15) 0.66296(16) 0.58777(9) 0.0390(3) Uani 1 1 d . . . H16A H 0.7965 0.6389 0.6119 0.047 Uiso 1 1 calc R . . C17 C 0.72484(18) 0.79596(16) 0.55596(10) 0.0462(4) Uani 1 1 d . . . H17A H 0.6783 0.8621 0.5828 0.055 Uiso 1 1 calc R . . H17B H 0.8196 0.8213 0.5511 0.055 Uiso 1 1 calc R . . C18 C 0.65936(15) 0.78097(16) 0.48936(9) 0.0410(3) Uani 1 1 d . . . C19 C 0.62340(19) 0.87496(17) 0.44337(11) 0.0512(4) Uani 1 1 d . . . H19A H 0.6339 0.9641 0.4533 0.061 Uiso 1 1 calc R . . C20 C 0.57212(18) 0.83642(19) 0.38294(11) 0.0524(5) Uani 1 1 d . . . H20A H 0.5467 0.9002 0.3516 0.063 Uiso 1 1 calc R . . C21 C 0.55710(17) 0.70674(19) 0.36714(9) 0.0466(4) Uani 1 1 d . . . H21A H 0.5240 0.6825 0.3249 0.056 Uiso 1 1 calc R . . C22 C 0.59047(15) 0.61243(16) 0.41299(8) 0.0386(3) Uani 1 1 d . . . H22A H 0.5794 0.5234 0.4030 0.046 Uiso 1 1 calc R . . C23 C 0.64035(14) 0.65115(14) 0.47378(8) 0.0353(3) Uani 1 1 d . . . C24 C 0.68322(14) 0.56684(14) 0.53043(8) 0.0342(3) Uani 1 1 d . . . H24A H 0.7620 0.5117 0.5192 0.041 Uiso 1 1 calc R . . N25 N 0.57364(12) 0.49220(11) 0.55911(6) 0.0310(2) Uani 1 1 d . . . S30 S 0.12784(4) 0.77844(4) 0.892962(18) 0.03715(10) Uani 1 1 d . . . O31 O 0.13503(18) 0.90312(12) 0.86240(7) 0.0606(4) Uani 1 1 d . . . O32 O -0.00415(11) 0.72462(13) 0.89762(6) 0.0490(3) Uani 1 1 d . . . O33 O 0.20528(14) 0.76383(15) 0.95229(6) 0.0579(4) Uani 1 1 d . . . C30 C 0.21105(18) 0.67345(17) 0.83384(9) 0.0454(4) Uani 1 1 d . . . F31 F 0.21110(18) 0.55220(12) 0.85447(8) 0.0834(5) Uani 1 1 d . . . F32 F 0.33555(12) 0.70966(17) 0.82415(7) 0.0784(4) Uani 1 1 d . . . F33 F 0.15003(16) 0.67681(14) 0.77582(6) 0.0741(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 0.0343(7) 0.0300(7) 0.0307(7) -0.0011(5) 0.0012(5) 0.0001(5) N2 0.0327(6) 0.0298(6) 0.0289(6) 0.0005(5) 0.0016(5) -0.0021(5) C3 0.0294(6) 0.0340(7) 0.0301(6) 0.0020(6) 0.0000(5) -0.0012(5) C4 0.0275(6) 0.0331(7) 0.0340(7) 0.0024(6) -0.0031(5) -0.0029(5) C5 0.0330(7) 0.0394(8) 0.0405(8) -0.0025(6) 0.0028(6) -0.0041(6) C6 0.0376(7) 0.0362(8) 0.0597(10) -0.0020(7) 0.0004(7) 0.0007(6) C7 0.0487(9) 0.0369(8) 0.0583(10) 0.0100(7) -0.0127(8) -0.0007(7) C8 0.0527(9) 0.0446(9) 0.0388(8) 0.0109(7) -0.0060(7) -0.0063(8) C9 0.0371(7) 0.0377(8) 0.0337(7) 0.0033(6) -0.0011(6) -0.0035(6) C10 0.0549(9) 0.0463(9) 0.0347(8) 0.0031(7) 0.0117(7) 0.0008(7) C11 0.0342(7) 0.0378(8) 0.0351(7) -0.0002(6) 0.0045(6) 0.0018(6) O12 0.0487(6) 0.0423(6) 0.0364(6) -0.0070(5) 0.0112(5) -0.0058(5) C13 0.0378(7) 0.0317(7) 0.0304(7) -0.0013(6) 0.0019(6) 0.0015(6) C14 0.0373(7) 0.0276(6) 0.0346(7) -0.0019(6) -0.0029(6) 0.0003(6) O15 0.0458(6) 0.0327(5) 0.0425(6) -0.0067(5) 0.0016(5) -0.0064(5) C16 0.0331(7) 0.0371(8) 0.0468(9) -0.0013(7) -0.0041(6) -0.0024(6) C17 0.0418(8) 0.0362(8) 0.0606(10) 0.0002(8) -0.0006(7) -0.0102(7) C18 0.0325(7) 0.0338(7) 0.0567(10) 0.0062(7) 0.0064(6) -0.0028(6) C19 0.0459(9) 0.0348(8) 0.0729(12) 0.0154(8) 0.0094(9) -0.0024(7) C20 0.0431(8) 0.0517(10) 0.0624(12) 0.0248(9) 0.0033(8) 0.0022(8) C21 0.0376(8) 0.0548(10) 0.0474(9) 0.0146(8) 0.0010(6) -0.0021(7) C22 0.0304(7) 0.0399(8) 0.0456(8) 0.0071(7) 0.0036(6) -0.0012(6) C23 0.0276(6) 0.0343(7) 0.0439(8) 0.0064(6) 0.0047(6) 0.0000(6) C24 0.0288(6) 0.0317(7) 0.0421(8) 0.0019(6) 0.0022(6) -0.0005(5) N25 0.0316(5) 0.0283(5) 0.0331(6) -0.0001(5) 0.0012(5) -0.0008(5) S30 0.04247(19) 0.03482(18) 0.03415(17) 0.00059(14) 0.00424(14) -0.00440(15) O31 0.0862(10) 0.0330(6) 0.0627(8) 0.0046(6) 0.0173(8) -0.0014(6) O32 0.0376(5) 0.0613(7) 0.0482(7) 0.0112(6) 0.0028(5) -0.0011(5) O33 0.0604(8) 0.0786(9) 0.0348(6) 0.0019(6) -0.0050(5) -0.0276(7) C30 0.0500(9) 0.0427(9) 0.0436(9) 0.0067(7) 0.0016(7) 0.0123(7) F31 0.1129(12) 0.0431(6) 0.0941(11) 0.0133(6) 0.0176(9) 0.0291(7) F32 0.0479(6) 0.1112(11) 0.0762(8) 0.0182(8) 0.0197(6) 0.0168(7) F33 0.0965(10) 0.0860(9) 0.0397(6) -0.0132(6) -0.0107(6) 0.0189(8) _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 N25 1.3314(19) . ? C1 N2 1.3358(19) . ? N2 C13 1.3766(19) . ? N2 C3 1.4637(18) . ? C3 C4 1.499(2) . ? C3 C11 1.561(2) . ? C4 C9 1.383(2) . ? C4 C5 1.385(2) . ? C5 C6 1.383(2) . ? C6 C7 1.390(3) . ? C7 C8 1.384(3) . ? C8 C9 1.393(2) . ? C9 C10 1.510(2) . ? C10 C11 1.523(2) . ? C11 O12 1.4755(19) . ? O12 C13 1.3411(19) . ? C13 C14 1.354(2) . ? C14 O15 1.3489(18) . ? C14 N25 1.3759(19) . ? O15 C16 1.479(2) . ? C16 C17 1.524(2) . ? C16 C24 1.557(2) . ? C17 C18 1.507(3) . ? C18 C23 1.393(2) . ? C18 C19 1.393(2) . ? C19 C20 1.385(3) . ? C20 C21 1.387(3) . ? C21 C22 1.387(2) . ? C22 C23 1.387(2) . ? C23 C24 1.503(2) . ? C24 N25 1.4627(18) . ? S30 O31 1.4323(13) . ? S30 O33 1.4377(13) . ? S30 O32 1.4385(12) . ? S30 C30 1.8185(18) . ? C30 F32 1.318(2) . ? C30 F31 1.322(2) . ? C30 F33 1.324(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N25 C1 N2 105.01(12) . . ? C1 N2 C13 111.37(12) . . ? C1 N2 C3 137.56(12) . . ? C13 N2 C3 111.07(11) . . ? N2 C3 C4 115.31(11) . . ? N2 C3 C11 100.97(11) . . ? C4 C3 C11 104.76(11) . . ? C9 C4 C5 121.19(15) . . ? C9 C4 C3 111.06(13) . . ? C5 C4 C3 127.70(14) . . ? C6 C5 C4 118.93(15) . . ? C5 C6 C7 120.27(16) . . ? C8 C7 C6 120.68(16) . . ? C7 C8 C9 119.09(16) . . ? C4 C9 C8 119.82(15) . . ? C4 C9 C10 111.61(14) . . ? C8 C9 C10 128.56(15) . . ? C9 C10 C11 105.11(12) . . ? O12 C11 C10 111.17(13) . . ? O12 C11 C3 106.48(11) . . ? C10 C11 C3 106.95(12) . . ? C13 O12 C11 107.41(11) . . ? O12 C13 C14 140.89(14) . . ? O12 C13 N2 113.11(12) . . ? C14 C13 N2 105.99(12) . . ? O15 C14 C13 141.34(14) . . ? O15 C14 N25 112.48(13) . . ? C13 C14 N25 106.13(12) . . ? C14 O15 C16 106.88(11) . . ? O15 C16 C17 110.49(13) . . ? O15 C16 C24 105.70(12) . . ? C17 C16 C24 106.06(13) . . ? C18 C17 C16 104.54(13) . . ? C23 C18 C19 119.10(17) . . ? C23 C18 C17 111.18(14) . . ? C19 C18 C17 129.65(16) . . ? C20 C19 C18 119.00(17) . . ? C19 C20 C21 121.47(16) . . ? C22 C21 C20 119.99(18) . . ? C23 C22 C21 118.49(16) . . ? C22 C23 C18 121.91(15) . . ? C22 C23 C24 127.74(14) . . ? C18 C23 C24 110.35(14) . . ? N25 C24 C23 113.22(12) . . ? N25 C24 C16 100.70(12) . . ? C23 C24 C16 104.64(12) . . ? C1 N25 C14 111.47(12) . . ? C1 N25 C24 137.39(13) . . ? C14 N25 C24 111.06(12) . . ? O31 S30 O33 115.35(9) . . ? O31 S30 O32 115.03(9) . . ? O33 S30 O32 113.66(8) . . ? O31 S30 C30 103.33(8) . . ? O33 S30 C30 103.83(9) . . ? O32 S30 C30 103.52(9) . . ? F32 C30 F31 108.44(16) . . ? F32 C30 F33 107.34(16) . . ? F31 C30 F33 107.77(17) . . ? F32 C30 S30 111.26(15) . . ? F31 C30 S30 111.04(13) . . ? F33 C30 S30 110.84(12) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 72.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.150 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.034 #===END data_16b _database_code_depnum_ccdc_archive 'CCDC 842972' #TrackingRef 'Org Lett 08-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 N2 O2, I, 4/3(C7 H16)' _chemical_formula_sum 'C32.33 H42.33 I N2 O2' _chemical_formula_weight 617.92 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' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 21.382(2) _cell_length_b 21.382(2) _cell_length_c 10.7536(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4257.7(8) _cell_formula_units_Z 6 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1916 _cell_measurement_theta_min 2.3841 _cell_measurement_theta_max 72.9898 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1916 _exptl_absorpt_coefficient_mu 9.102 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.375 _exptl_absorpt_correction_T_max 0.792 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10176 _diffrn_reflns_av_R_equivalents 0.0675 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 73.15 _reflns_number_total 3982 _reflns_number_gt 1503 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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. Results of chirality/polarity tests _refine_ls_R_factor_obs+ 0.0916 _refine_ls_wR_factor_obs+ 0.2924 _refine_ls_abs_structure_Flack+ 0.08(3) _refine_ls_R_factor_obs- 0.1144 _refine_ls_wR_factor_obs- 0.3388 _refine_ls_abs_structure_Flack- 0.92(3) ; _chemical_absolute_configuration ad _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^)+(0.1836P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 1059 Friedel pairs' _refine_ls_abs_structure_Flack 0.05(2) _refine_ls_number_reflns 3982 _refine_ls_number_parameters 243 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1600 _refine_ls_R_factor_gt 0.0916 _refine_ls_wR_factor_ref 0.3676 _refine_ls_wR_factor_gt 0.2924 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.067 _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 0.4818(11) 0.3819(10) 0.2324(19) 0.160(6) Uani 1 1 d . . . H1A H 0.4887 0.4246 0.2719 0.192 Uiso 1 1 calc R . . N2 N 0.4995(9) 0.3347(8) 0.2766(11) 0.157(4) Uani 1 1 d . . . C3 C 0.5372(11) 0.3240(10) 0.3791(13) 0.151(5) Uani 1 1 d . . . H3A H 0.5186 0.3292 0.4614 0.181 Uiso 1 1 calc R . . C4 C 0.6167(13) 0.3640(12) 0.3751(13) 0.160(6) Uani 1 1 d . . . C5 C 0.6637(17) 0.4395(14) 0.3793(15) 0.170(6) Uani 1 1 d . . . C6 C 0.738(2) 0.4637(15) 0.380(2) 0.224(13) Uani 1 1 d . . . H6A H 0.7697 0.5140 0.3915 0.268 Uiso 1 1 calc R . . C7 C 0.7690(15) 0.4217(15) 0.3642(17) 0.172(7) Uani 1 1 d . . . H7A H 0.8199 0.4429 0.3583 0.206 Uiso 1 1 calc R . . C8 C 0.7259(12) 0.3500(18) 0.3578(17) 0.190(9) Uani 1 1 d . . . H8A H 0.7462 0.3195 0.3499 0.228 Uiso 1 1 calc R . . C9 C 0.6483(15) 0.3189(13) 0.3630(13) 0.166(7) Uani 1 1 d . . . C10 C 0.5858(12) 0.2416(10) 0.3721(16) 0.164(6) Uani 1 1 d . . . H10A H 0.5854 0.2214 0.4552 0.197 Uiso 1 1 calc R . . H10B H 0.5911 0.2111 0.3085 0.197 Uiso 1 1 calc R . . C11 C 0.5144(11) 0.2421(9) 0.3511(15) 0.147(5) Uani 1 1 d . . . H11A H 0.4737 0.2066 0.4043 0.176 Uiso 1 1 calc R . . O12 O 0.4996(8) 0.2318(7) 0.2248(10) 0.166(4) Uani 1 1 d . . . C13 C 0.4839(12) 0.2822(9) 0.1895(16) 0.159(6) Uani 1 1 d . . . C14 C 0.4558(10) 0.2973(7) 0.0904(16) 0.151(5) Uani 1 1 d . . . O15 O 0.4253(8) 0.2715(6) -0.0180(12) 0.171(4) Uani 1 1 d . . . C16 C 0.4147(14) 0.3245(12) -0.0820(19) 0.187(8) Uani 1 1 d . . . H16A H 0.4545 0.3511 -0.1434 0.224 Uiso 1 1 calc R . . C17 C 0.3455(14) 0.2915(14) -0.145(2) 0.194(8) Uani 1 1 d . . . H17A H 0.3284 0.2406 -0.1671 0.233 Uiso 1 1 calc R . . H17B H 0.3467 0.3189 -0.2197 0.233 Uiso 1 1 calc R . . C18 C 0.3003(15) 0.2979(10) -0.0409(14) 0.195(9) Uani 1 1 d G . . C19 C 0.2254(14) 0.2623(9) -0.034(2) 0.251(14) Uani 1 1 d G . . H19A H 0.1972 0.2272 -0.0951 0.301 Uiso 1 1 calc R . . C20 C 0.1917(9) 0.2781(12) 0.061(3) 0.253(15) Uani 1 1 d G . . H20A H 0.1405 0.2537 0.0658 0.303 Uiso 1 1 calc R . . C21 C 0.2329(13) 0.3295(14) 0.150(2) 0.266(15) Uani 1 1 d GU . . H21A H 0.2099 0.3402 0.2156 0.319 Uiso 1 1 calc R . . C22 C 0.3079(13) 0.3651(10) 0.1437(15) 0.218(10) Uani 1 1 d GU . . C23 C 0.3415(9) 0.3493(8) 0.0481(16) 0.174(8) Uani 1 1 d G . . C24 C 0.4194(12) 0.3737(11) 0.018(2) 0.171(7) Uani 1 1 d . . . H24A H 0.4475 0.4257 -0.0069 0.206 Uiso 1 1 calc R . . N25 N 0.4520(9) 0.3567(8) 0.1204(12) 0.159(4) Uani 1 1 d . . . C26 C 0.6362(15) 0.4954(10) 0.392(2) 0.194(9) Uani 1 1 d . . . H26A H 0.6767 0.5428 0.4149 0.291 Uiso 1 1 calc R . . H26B H 0.5987 0.4789 0.4556 0.291 Uiso 1 1 calc R . . H26C H 0.6163 0.4993 0.3117 0.291 Uiso 1 1 calc R . . C27 C 0.3590(16) 0.4291(16) 0.245(4) 0.245(12) Uani 1 1 d U . . H27A H 0.4045 0.4292 0.2569 0.367 Uiso 1 1 calc R . . H27B H 0.3336 0.4197 0.3244 0.367 Uiso 1 1 calc R . . H27C H 0.3692 0.4762 0.2128 0.367 Uiso 1 1 calc R . . I1 I 0.55689(12) 0.57309(7) 0.08552(19) 0.2126(10) 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 0.225(15) 0.170(12) 0.124(13) -0.003(11) 0.034(12) 0.126(13) N2 0.218(12) 0.160(10) 0.081(8) -0.013(7) 0.010(8) 0.085(9) C3 0.209(15) 0.191(13) 0.075(9) 0.016(8) 0.035(9) 0.116(13) C4 0.223(18) 0.182(15) 0.067(7) -0.023(8) 0.010(9) 0.095(13) C5 0.25(2) 0.200(19) 0.073(9) -0.025(10) -0.017(12) 0.122(17) C6 0.35(4) 0.185(18) 0.100(14) -0.027(12) -0.02(2) 0.10(3) C7 0.225(19) 0.185(16) 0.088(10) 0.003(11) 0.007(11) 0.091(16) C8 0.184(16) 0.28(3) 0.077(9) 0.031(13) 0.005(10) 0.096(17) C9 0.26(2) 0.206(17) 0.060(6) -0.019(9) -0.009(10) 0.134(18) C10 0.231(17) 0.180(14) 0.100(10) -0.006(10) -0.015(11) 0.116(14) C11 0.230(15) 0.168(10) 0.107(10) 0.022(8) 0.016(10) 0.148(11) O12 0.222(10) 0.194(9) 0.092(7) 0.001(7) 0.007(7) 0.111(8) C13 0.241(18) 0.142(10) 0.103(10) 0.008(9) -0.043(11) 0.103(12) C14 0.222(15) 0.126(8) 0.110(12) -0.010(9) 0.018(12) 0.091(9) O15 0.234(12) 0.154(8) 0.110(7) -0.005(7) -0.038(8) 0.087(8) C16 0.26(2) 0.209(17) 0.094(11) 0.028(13) 0.020(14) 0.118(17) C17 0.23(2) 0.198(17) 0.124(14) 0.014(13) -0.026(15) 0.081(16) C18 0.26(2) 0.157(14) 0.19(2) -0.004(15) -0.02(2) 0.113(15) C19 0.32(4) 0.25(3) 0.20(3) 0.04(3) -0.03(3) 0.16(3) C20 0.30(3) 0.34(4) 0.23(3) 0.01(3) -0.02(3) 0.24(3) C21 0.29(2) 0.28(2) 0.28(3) 0.032(16) -0.002(17) 0.183(18) C22 0.240(17) 0.223(16) 0.219(19) 0.031(14) 0.003(14) 0.136(14) C23 0.29(2) 0.145(11) 0.130(14) 0.045(11) 0.049(15) 0.139(14) C24 0.219(17) 0.180(14) 0.139(15) 0.059(12) 0.038(13) 0.118(13) N25 0.223(13) 0.165(10) 0.088(8) -0.017(7) -0.006(8) 0.097(10) C26 0.30(3) 0.147(11) 0.121(13) -0.002(10) 0.015(15) 0.104(13) C27 0.284(19) 0.252(17) 0.26(2) 0.068(15) -0.012(15) 0.179(15) I1 0.323(2) 0.1787(11) 0.1207(9) -0.0114(8) -0.0271(11) 0.1137(13) _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 N2 1.33(2) . ? C1 N25 1.34(3) . ? N2 C13 1.37(2) . ? N2 C3 1.45(2) . ? C3 C4 1.47(3) . ? C3 C11 1.59(2) . ? C4 C5 1.41(3) . ? C4 C9 1.43(3) . ? C5 C6 1.40(4) . ? C5 C26 1.58(3) . ? C6 C7 1.37(4) . ? C7 C8 1.34(3) . ? C8 C9 1.45(3) . ? C9 C10 1.52(3) . ? C10 C11 1.55(3) . ? C11 O12 1.39(2) . ? O12 C13 1.334(19) . ? C13 C14 1.34(3) . ? C14 O15 1.31(2) . ? C14 N25 1.351(19) . ? O15 C16 1.43(2) . ? C16 C17 1.45(3) . ? C16 C24 1.47(3) . ? C17 C18 1.53(3) . ? C18 C19 1.3900 . ? C18 C23 1.3900 . ? C19 C20 1.3900 . ? C20 C21 1.3900 . ? C21 C22 1.3900 . ? C22 C23 1.3900 . ? C22 C27 1.66(4) . ? C23 C24 1.51(3) . ? C24 N25 1.44(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N25 105.9(14) . . ? C1 N2 C13 109.4(15) . . ? C1 N2 C3 141.5(16) . . ? C13 N2 C3 108.5(15) . . ? N2 C3 C4 117.3(14) . . ? N2 C3 C11 98.1(14) . . ? C4 C3 C11 105.3(14) . . ? C5 C4 C9 118(2) . . ? C5 C4 C3 128(2) . . ? C9 C4 C3 114.0(19) . . ? C6 C5 C4 117(2) . . ? C6 C5 C26 120(3) . . ? C4 C5 C26 123(2) . . ? C7 C6 C5 126(3) . . ? C8 C7 C6 119(3) . . ? C7 C8 C9 120(3) . . ? C4 C9 C8 121(2) . . ? C4 C9 C10 106(2) . . ? C8 C9 C10 133(2) . . ? C9 C10 C11 108.4(15) . . ? O12 C11 C10 106.9(13) . . ? O12 C11 C3 106.2(11) . . ? C10 C11 C3 102.6(16) . . ? C13 O12 C11 106.3(12) . . ? O12 C13 C14 138.1(15) . . ? O12 C13 N2 114.3(14) . . ? C14 C13 N2 107.6(14) . . ? O15 C14 C13 142.4(13) . . ? O15 C14 N25 110.8(16) . . ? C13 C14 N25 106.3(15) . . ? C14 O15 C16 109.5(13) . . ? O15 C16 C17 111.4(19) . . ? O15 C16 C24 103.5(15) . . ? C17 C16 C24 112(2) . . ? C16 C17 C18 99(2) . . ? C19 C18 C23 120.0 . . ? C19 C18 C17 126.6(19) . . ? C23 C18 C17 113.2(19) . . ? C20 C19 C18 120.0 . . ? C19 C20 C21 120.0 . . ? C22 C21 C20 120.0 . . ? C23 C22 C21 120.0 . . ? C23 C22 C27 118.5(18) . . ? C21 C22 C27 121.5(18) . . ? C22 C23 C18 120.0 . . ? C22 C23 C24 133.6(18) . . ? C18 C23 C24 106.3(18) . . ? N25 C24 C16 104.2(15) . . ? N25 C24 C23 109.7(15) . . ? C16 C24 C23 104(2) . . ? C1 N25 C14 110.6(15) . . ? C1 N25 C24 140.8(16) . . ? C14 N25 C24 108.6(15) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 72.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.258 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.059 #===END data_17a _database_code_depnum_ccdc_archive 'CCDC 842973' #TrackingRef 'Org Lett 08-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 N2 O2, C F3 O3 S' _chemical_formula_sum 'C34 H25 F3 N2 O5 S' _chemical_formula_weight 630.62 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.31659(11) _cell_length_b 20.0565(2) _cell_length_c 17.4123(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.0536(12) _cell_angle_gamma 90.00 _cell_volume 2893.11(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 7113 _cell_measurement_theta_min 2.2010 _cell_measurement_theta_max 72.1864 _exptl_crystal_description tablets _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 1.577 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.830 _exptl_absorpt_correction_T_max 0.934 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11603 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 72.33 _reflns_number_total 8580 _reflns_number_gt 7605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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. Results of chirality/polarity tests _refine_ls_R_factor_obs+ 0.0388 _refine_ls_wR_factor_obs+ 0.0979 _refine_ls_abs_structure_Flack+ 0.054(15) _refine_ls_R_factor_obs- 0.0471 _refine_ls_wR_factor_obs- 0.1210 _refine_ls_abs_structure_Flack- 0.946(15) ; _chemical_absolute_configuration ad _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^)+(0.0657P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 2970 Friedel pairs' _refine_ls_abs_structure_Flack 0.051(15) _refine_ls_number_reflns 8580 _refine_ls_number_parameters 845 _refine_ls_number_restraints 188 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.020 _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 C1A C 0.4859(3) 0.67659(13) 1.01252(14) 0.0347(5) Uani 1 1 d . . . H1AA H 0.4080 0.6776 1.0492 0.042 Uiso 1 1 calc R . . N2A N 0.5637(2) 0.62323(10) 0.98823(12) 0.0347(4) Uani 1 1 d . . . C3A C 0.5846(3) 0.55199(14) 1.00729(16) 0.0390(5) Uani 1 1 d . . . H3AA H 0.4803 0.5287 1.0135 0.047 Uiso 1 1 calc R . . C4A C 0.7128(3) 0.53803(13) 1.07286(17) 0.0398(6) Uani 1 1 d . . . C5A C 0.7253(3) 0.56300(14) 1.14775(16) 0.0402(6) Uani 1 1 d . . . C6A C 0.8618(4) 0.54503(15) 1.19610(18) 0.0465(6) Uani 1 1 d . . . H6AA H 0.8745 0.5618 1.2473 0.056 Uiso 1 1 calc R . . C7A C 0.9788(4) 0.50327(17) 1.17087(19) 0.0532(7) Uani 1 1 d . . . H7AA H 1.0694 0.4912 1.2051 0.064 Uiso 1 1 calc R . . C8A C 0.9648(4) 0.47910(16) 1.0964(2) 0.0518(7) Uani 1 1 d . . . H8AA H 1.0458 0.4507 1.0792 0.062 Uiso 1 1 calc R . . C9A C 0.8324(3) 0.49638(14) 1.04712(18) 0.0454(6) Uani 1 1 d . . . C10A C 0.7932(4) 0.47813(15) 0.96362(19) 0.0513(7) Uani 1 1 d . . . H10A H 0.7502 0.4322 0.9586 0.062 Uiso 1 1 calc R . . H10B H 0.8901 0.4816 0.9347 0.062 Uiso 1 1 calc R . . C11A C 0.6663(3) 0.52862(15) 0.93458(17) 0.0433(6) Uani 1 1 d . . . H11A H 0.5866 0.5096 0.8941 0.052 Uiso 1 1 calc R . . O12A O 0.7472(2) 0.58877(10) 0.90745(11) 0.0441(4) Uani 1 1 d . . . C13A C 0.6669(3) 0.64104(14) 0.93377(15) 0.0370(5) Uani 1 1 d . . . C14A C 0.6536(3) 0.70819(14) 0.92522(14) 0.0365(5) Uani 1 1 d . . . O15A O 0.7146(2) 0.75893(10) 0.88698(11) 0.0417(4) Uani 1 1 d . . . C16A C 0.6698(3) 0.82008(14) 0.92814(16) 0.0425(6) Uani 1 1 d . . . H16A H 0.7572 0.8349 0.9676 0.051 Uiso 1 1 calc R . . C17A C 0.6218(4) 0.87401(15) 0.87065(17) 0.0479(6) Uani 1 1 d . . . H17A H 0.6369 0.9187 0.8942 0.057 Uiso 1 1 calc R . . H17B H 0.6856 0.8711 0.8254 0.057 Uiso 1 1 calc R . . C18A C 0.4466(4) 0.86024(13) 0.84829(16) 0.0422(6) Uani 1 1 d . . . C19A C 0.3506(4) 0.88214(15) 0.78469(17) 0.0477(7) Uani 1 1 d . . . H19A H 0.3934 0.9114 0.7488 0.057 Uiso 1 1 calc R . . C20A C 0.1916(4) 0.86128(16) 0.77340(18) 0.0524(7) Uani 1 1 d . . . H20A H 0.1257 0.8756 0.7291 0.063 Uiso 1 1 calc R . . C21A C 0.1280(4) 0.81930(15) 0.82689(17) 0.0464(6) Uani 1 1 d . . . H21A H 0.0190 0.8049 0.8183 0.056 Uiso 1 1 calc R . . C22A C 0.2213(3) 0.79799(13) 0.89274(15) 0.0383(6) Uani 1 1 d . . . C23A C 0.3821(3) 0.81806(12) 0.90211(14) 0.0363(5) Uani 1 1 d . . . C24A C 0.5131(3) 0.80010(13) 0.96484(15) 0.0377(5) Uani 1 1 d . . . H24A H 0.5006 0.8234 1.0147 0.045 Uiso 1 1 calc R . . N25A N 0.5412(2) 0.72802(11) 0.97417(12) 0.0350(4) Uani 1 1 d . . . C26A C 0.6035(3) 0.60992(14) 1.17388(14) 0.0397(6) Uani 1 1 d . . . C27A C 0.6408(4) 0.67698(15) 1.18583(16) 0.0462(6) Uani 1 1 d . . . H27A H 0.7475 0.6920 1.1805 0.055 Uiso 1 1 calc R . . C28A C 0.5258(4) 0.72195(17) 1.20530(18) 0.0543(8) Uani 1 1 d . . . H28A H 0.5529 0.7677 1.2124 0.065 Uiso 1 1 calc R . . C29A C 0.3710(4) 0.7002(2) 1.2145(2) 0.0626(9) Uani 1 1 d . . . H29A H 0.2912 0.7310 1.2277 0.075 Uiso 1 1 calc R . . C30A C 0.3329(4) 0.6342(2) 1.2047(2) 0.0629(9) Uani 1 1 d . . . H30A H 0.2269 0.6194 1.2121 0.075 Uiso 1 1 calc R . . C31A C 0.4471(4) 0.58890(17) 1.18402(18) 0.0507(7) Uani 1 1 d . . . H31A H 0.4186 0.5433 1.1767 0.061 Uiso 1 1 calc R . . C32A C 0.1508(3) 0.75361(13) 0.95002(15) 0.0372(5) Uani 1 1 d . . . C33A C 0.1305(3) 0.68558(15) 0.93489(17) 0.0449(6) Uani 1 1 d . . . H33A H 0.1585 0.6677 0.8873 0.054 Uiso 1 1 calc R . . C34A C 0.0696(4) 0.64407(15) 0.98917(19) 0.0506(7) Uani 1 1 d . . . H34A H 0.0588 0.5976 0.9793 0.061 Uiso 1 1 calc R . . C35A C 0.0249(4) 0.66997(18) 1.05702(19) 0.0551(7) Uani 1 1 d . . . H35A H -0.0166 0.6414 1.0941 0.066 Uiso 1 1 calc R . . C36A C 0.0401(5) 0.73767(19) 1.0716(2) 0.0618(9) Uani 1 1 d . . . H36A H 0.0060 0.7557 1.1179 0.074 Uiso 1 1 calc R . . C37A C 0.1051(4) 0.77896(16) 1.01871(17) 0.0494(7) Uani 1 1 d . . . H37A H 0.1185 0.8251 1.0297 0.059 Uiso 1 1 calc R . . C1B C 0.4518(3) 0.68939(13) 0.48120(14) 0.0371(5) Uani 1 1 d . . . H1BA H 0.3736 0.6897 0.5178 0.045 Uiso 1 1 calc R . . N2B N 0.5232(3) 0.63649(11) 0.45309(12) 0.0365(5) Uani 1 1 d . . . C3B C 0.5288(3) 0.56313(13) 0.46270(16) 0.0406(6) Uani 1 1 d . . . H3BA H 0.4201 0.5427 0.4666 0.049 Uiso 1 1 calc R . . C4B C 0.6548(4) 0.54027(13) 0.52630(17) 0.0423(6) Uani 1 1 d . . . C5B C 0.6689(4) 0.55606(14) 0.60451(16) 0.0450(6) Uani 1 1 d . . . C6B C 0.8044(4) 0.53090(17) 0.64832(19) 0.0538(8) Uani 1 1 d . . . H6BA H 0.8193 0.5414 0.7017 0.065 Uiso 1 1 calc R . . C7B C 0.9174(4) 0.49118(17) 0.6166(2) 0.0569(8) Uani 1 1 d . . . H7BA H 1.0076 0.4748 0.6483 0.068 Uiso 1 1 calc R . . C8B C 0.9002(4) 0.47522(15) 0.53931(19) 0.0517(7) Uani 1 1 d . . . H8BA H 0.9785 0.4484 0.5173 0.062 Uiso 1 1 calc R . . C9B C 0.7670(4) 0.49890(13) 0.49441(17) 0.0454(6) Uani 1 1 d . . . C10B C 0.7235(4) 0.48770(15) 0.40928(18) 0.0491(7) Uani 1 1 d . . . H10C H 0.8199 0.4910 0.3799 0.059 Uiso 1 1 calc R . . H10D H 0.6724 0.4435 0.3996 0.059 Uiso 1 1 calc R . . C11B C 0.6058(3) 0.54341(13) 0.38816(16) 0.0426(6) Uani 1 1 d . . . H11B H 0.5229 0.5304 0.3457 0.051 Uiso 1 1 calc R . . O12B O 0.6990(2) 0.60283(10) 0.36806(11) 0.0434(4) Uani 1 1 d . . . C13B C 0.6284(3) 0.65479(13) 0.39991(14) 0.0366(5) Uani 1 1 d . . . C14B C 0.6252(3) 0.72236(13) 0.39728(14) 0.0356(5) Uani 1 1 d . . . O15B O 0.6928(2) 0.77353(10) 0.36277(11) 0.0415(4) Uani 1 1 d . . . C16B C 0.6431(4) 0.83447(14) 0.40152(16) 0.0447(6) Uani 1 1 d . A . H16B H 0.7281 0.8510 0.4411 0.054 Uiso 1 1 calc R . . C17B C 0.5954(4) 0.88628(15) 0.34089(19) 0.0528(7) Uani 1 1 d . . . H17C H 0.6088 0.9319 0.3623 0.063 Uiso 1 1 calc R . . H17D H 0.6607 0.8819 0.2963 0.063 Uiso 1 1 calc R . . C18B C 0.4201(4) 0.87116(13) 0.31801(17) 0.0458(6) Uani 1 1 d . . . C19B C 0.3267(4) 0.88869(16) 0.25175(18) 0.0538(7) Uani 1 1 d . . . H19B H 0.3715 0.9150 0.2136 0.065 Uiso 1 1 calc R . . C20B C 0.1688(4) 0.86806(17) 0.24089(19) 0.0587(8) Uani 1 1 d . . . H20B H 0.1037 0.8807 0.1957 0.070 Uiso 1 1 calc R . . C21B C 0.1046(4) 0.82866(16) 0.29627(19) 0.0542(7) Uani 1 1 d . A . H21B H -0.0046 0.8146 0.2881 0.065 Uiso 1 1 calc R . . C22B C 0.1955(4) 0.80940(15) 0.36301(18) 0.0467(6) Uani 1 1 d D . . C23B C 0.3551(3) 0.83080(13) 0.37356(16) 0.0417(6) Uani 1 1 d . A . C24B C 0.4856(3) 0.81460(13) 0.43709(16) 0.0411(6) Uani 1 1 d . . . H24B H 0.4709 0.8382 0.4866 0.049 Uiso 1 1 calc R A . N25B N 0.5136(3) 0.74199(11) 0.44695(12) 0.0362(4) Uani 1 1 d . A . C26B C 0.5488(4) 0.59702(15) 0.64161(16) 0.0487(7) Uani 1 1 d . . . C27B C 0.5976(5) 0.64990(17) 0.69066(19) 0.0615(9) Uani 1 1 d . . . H27B H 0.7090 0.6608 0.6991 0.074 Uiso 1 1 calc R . . C28B C 0.4851(6) 0.68661(19) 0.7271(2) 0.0753(12) Uani 1 1 d . . . H28B H 0.5199 0.7226 0.7599 0.090 Uiso 1 1 calc R . . C29B C 0.3235(6) 0.6712(2) 0.7162(2) 0.0729(11) Uani 1 1 d . . . H29B H 0.2472 0.6964 0.7415 0.087 Uiso 1 1 calc R . . C30B C 0.2725(5) 0.61921(18) 0.6685(2) 0.0642(9) Uani 1 1 d . . . H30B H 0.1610 0.6084 0.6611 0.077 Uiso 1 1 calc R . . C31B C 0.3841(4) 0.58255(15) 0.63103(18) 0.0525(7) Uani 1 1 d . . . H31B H 0.3478 0.5471 0.5977 0.063 Uiso 1 1 calc R . . C32B C 0.1261(5) 0.7611(2) 0.4156(3) 0.0467(14) Uani 0.685(14) 1 d PGDU A 1 C33B C 0.0880(5) 0.6969(2) 0.3904(3) 0.0574(15) Uani 0.685(14) 1 d PGU A 1 H33B H 0.1017 0.6844 0.3387 0.069 Uiso 0.685(14) 1 calc PR A 1 C34B C 0.0297(5) 0.6507(3) 0.4407(4) 0.075(2) Uani 0.685(14) 1 d PGU A 1 H34B H 0.0037 0.6068 0.4234 0.090 Uiso 0.685(14) 1 calc PR A 1 C35B C 0.0096(4) 0.6689(4) 0.5163(4) 0.075(3) Uani 0.685(14) 1 d PGU A 1 H35B H -0.0302 0.6374 0.5507 0.090 Uiso 0.685(14) 1 calc PR A 1 C36B C 0.0477(6) 0.7332(4) 0.5415(3) 0.075(2) Uani 0.685(14) 1 d PGU A 1 H36B H 0.0340 0.7456 0.5932 0.090 Uiso 0.685(14) 1 calc PR A 1 C37B C 0.1059(7) 0.7793(3) 0.4912(3) 0.0598(16) Uani 0.685(14) 1 d PGU A 1 H37B H 0.1320 0.8233 0.5085 0.072 Uiso 0.685(14) 1 calc PR A 1 C32" C 0.1347(17) 0.7698(6) 0.4317(6) 0.055(4) Uiso 0.315(14) 1 d PGDU A 2 C33" C 0.0670(16) 0.7074(6) 0.4160(6) 0.060(4) Uiso 0.315(14) 1 d PGU A 2 H33C H 0.0610 0.6901 0.3650 0.072 Uiso 0.315(14) 1 calc PR A 2 C34" C 0.0082(12) 0.6703(5) 0.4748(8) 0.064(4) Uiso 0.315(14) 1 d PGU A 2 H34C H -0.0381 0.6276 0.4641 0.077 Uiso 0.315(14) 1 calc PR A 2 C35" C 0.0170(13) 0.6956(6) 0.5494(7) 0.069(4) Uiso 0.315(14) 1 d PGU A 2 H35C H -0.0232 0.6702 0.5896 0.083 Uiso 0.315(14) 1 calc PR A 2 C36" C 0.0847(16) 0.7580(6) 0.5651(5) 0.073(4) Uiso 0.315(14) 1 d PGU A 2 H36C H 0.0908 0.7753 0.6161 0.088 Uiso 0.315(14) 1 calc PR A 2 C37" C 0.1436(17) 0.7951(5) 0.5062(6) 0.058(4) Uiso 0.315(14) 1 d PGU A 2 H37C H 0.1898 0.8378 0.5170 0.070 Uiso 0.315(14) 1 calc PR A 2 S40 S 0.75936(9) 0.91914(4) 0.62048(4) 0.04899(17) Uani 1 1 d . . . O41 O 0.7055(4) 0.95541(14) 0.68466(16) 0.0740(7) Uani 1 1 d . . . O42 O 0.6730(3) 0.93319(11) 0.54774(14) 0.0602(6) Uani 1 1 d . . . O43 O 0.9307(3) 0.91233(15) 0.61911(16) 0.0719(7) Uani 1 1 d . . . C40 C 0.6959(4) 0.83433(17) 0.63964(16) 0.0497(7) Uani 1 1 d . . . F41 F 0.7302(2) 0.79254(9) 0.58455(11) 0.0600(5) Uani 1 1 d . . . F42 F 0.7651(3) 0.81110(12) 0.70571(11) 0.0725(6) Uani 1 1 d . . . F43 F 0.5360(2) 0.83101(12) 0.64223(14) 0.0724(6) Uani 1 1 d . . . S50 S 0.25953(12) 0.41480(8) 0.88862(9) 0.0380(3) Uani 0.699(4) 1 d PDU B 1 O51 O 0.4182(4) 0.41883(19) 0.9224(3) 0.0651(11) Uani 0.699(4) 1 d PDU B 1 O52 O 0.2334(6) 0.36480(18) 0.8294(2) 0.0792(12) Uani 0.699(4) 1 d PDU B 1 O53 O 0.1330(5) 0.4146(2) 0.9379(2) 0.0808(13) Uani 0.699(4) 1 d PDU B 1 C50 C 0.2329(9) 0.4930(3) 0.8361(3) 0.049(2) Uani 0.699(4) 1 d PDU B 1 F51 F 0.0850(4) 0.5009(2) 0.8038(3) 0.0909(14) Uani 0.699(4) 1 d PDU B 1 F52 F 0.2646(5) 0.54521(14) 0.8821(2) 0.0738(10) Uani 0.699(4) 1 d PDU B 1 F53 F 0.3367(5) 0.49796(15) 0.78349(18) 0.0769(11) Uani 0.699(4) 1 d PDU B 1 S50' S 0.2528(4) 0.4350(2) 0.9063(2) 0.0431(10) Uiso 0.301(4) 1 d PDU B 2 O51' O 0.4112(11) 0.4114(5) 0.8866(5) 0.058(3) Uiso 0.301(4) 1 d PDU B 2 O52' O 0.2449(9) 0.4675(4) 0.9761(4) 0.0541(18) Uiso 0.301(4) 1 d PDU B 2 O53' O 0.1318(10) 0.3852(4) 0.8846(5) 0.060(2) Uiso 0.301(4) 1 d PDU B 2 C50' C 0.2091(14) 0.4993(5) 0.8340(6) 0.040(5) Uiso 0.301(4) 1 d PDU B 2 F51' F 0.0673(10) 0.5262(4) 0.8397(5) 0.067(2) Uiso 0.301(4) 1 d PDU B 2 F52' F 0.2149(9) 0.4778(3) 0.7630(3) 0.0577(17) Uiso 0.301(4) 1 d PDU B 2 F53' F 0.3160(9) 0.5484(4) 0.8413(5) 0.067(2) Uiso 0.301(4) 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 C1A 0.0334(12) 0.0355(13) 0.0345(12) -0.0010(10) -0.0002(9) 0.0037(10) N2A 0.0325(10) 0.0331(11) 0.0381(10) -0.0004(8) 0.0011(8) 0.0009(8) C3A 0.0361(12) 0.0322(12) 0.0487(14) -0.0047(11) 0.0038(10) -0.0005(10) C4A 0.0376(13) 0.0297(12) 0.0522(15) 0.0040(11) 0.0045(11) -0.0005(10) C5A 0.0370(13) 0.0338(13) 0.0501(15) 0.0083(11) 0.0049(11) -0.0035(11) C6A 0.0450(15) 0.0443(15) 0.0497(16) 0.0107(12) 0.0012(12) 0.0017(12) C7A 0.0425(15) 0.0519(17) 0.0641(19) 0.0209(15) -0.0012(13) 0.0041(13) C8A 0.0446(15) 0.0396(15) 0.072(2) 0.0129(14) 0.0090(13) 0.0065(13) C9A 0.0414(14) 0.0302(13) 0.0652(18) 0.0034(12) 0.0080(12) 0.0025(11) C10A 0.0455(15) 0.0377(14) 0.0708(19) -0.0101(14) 0.0062(13) 0.0031(13) C11A 0.0392(13) 0.0395(14) 0.0513(15) -0.0110(12) 0.0041(11) -0.0012(11) O12A 0.0409(9) 0.0430(10) 0.0491(10) -0.0093(8) 0.0078(8) 0.0023(8) C13A 0.0313(12) 0.0421(14) 0.0371(12) -0.0044(11) 0.0007(9) 0.0031(11) C14A 0.0305(11) 0.0430(14) 0.0352(12) 0.0008(10) -0.0008(9) -0.0008(10) O15A 0.0405(9) 0.0410(10) 0.0439(10) -0.0006(8) 0.0055(7) -0.0023(8) C16A 0.0427(14) 0.0407(14) 0.0434(14) -0.0063(11) 0.0001(10) -0.0067(11) C17A 0.0567(16) 0.0405(15) 0.0469(15) -0.0014(12) 0.0069(12) -0.0080(13) C18A 0.0520(15) 0.0328(13) 0.0420(14) -0.0023(10) 0.0048(11) 0.0049(12) C19A 0.0620(18) 0.0388(15) 0.0423(14) 0.0065(12) 0.0049(12) 0.0115(13) C20A 0.0616(18) 0.0495(17) 0.0448(16) 0.0057(13) -0.0031(13) 0.0199(15) C21A 0.0442(15) 0.0471(16) 0.0466(15) -0.0015(12) -0.0034(11) 0.0123(12) C22A 0.0418(14) 0.0318(13) 0.0413(13) -0.0031(10) 0.0026(10) 0.0081(10) C23A 0.0437(14) 0.0282(12) 0.0367(12) -0.0040(10) 0.0021(10) 0.0037(10) C24A 0.0421(13) 0.0333(13) 0.0372(13) -0.0046(10) 0.0003(10) -0.0023(11) N25A 0.0343(10) 0.0363(11) 0.0340(10) -0.0010(8) 0.0006(8) 0.0020(8) C26A 0.0415(14) 0.0418(14) 0.0350(12) 0.0049(11) -0.0011(10) 0.0033(12) C27A 0.0495(15) 0.0427(16) 0.0454(14) -0.0029(12) -0.0024(12) -0.0017(13) C28A 0.069(2) 0.0459(17) 0.0462(16) -0.0121(13) -0.0029(14) 0.0108(15) C29A 0.0584(19) 0.068(2) 0.0621(19) -0.0157(17) 0.0076(15) 0.0188(17) C30A 0.0451(17) 0.073(2) 0.072(2) -0.0072(18) 0.0110(15) 0.0045(16) C31A 0.0461(15) 0.0508(17) 0.0556(16) 0.0000(14) 0.0073(12) 0.0021(14) C32A 0.0289(11) 0.0363(13) 0.0456(14) 0.0006(11) -0.0012(10) 0.0023(10) C33A 0.0464(14) 0.0388(14) 0.0494(14) -0.0055(12) 0.0039(11) -0.0004(12) C34A 0.0430(15) 0.0407(15) 0.0668(18) -0.0004(13) -0.0026(13) -0.0087(12) C35A 0.0527(17) 0.0559(18) 0.0573(17) 0.0057(15) 0.0082(13) -0.0148(15) C36A 0.074(2) 0.0583(19) 0.0557(18) -0.0108(15) 0.0223(16) -0.0182(17) C37A 0.0559(17) 0.0414(15) 0.0515(16) -0.0075(13) 0.0089(13) -0.0049(13) C1B 0.0395(13) 0.0351(13) 0.0365(12) 0.0017(10) 0.0026(9) 0.0005(11) N2B 0.0404(11) 0.0311(10) 0.0371(11) 0.0030(9) -0.0007(8) -0.0012(9) C3B 0.0471(15) 0.0289(12) 0.0446(14) 0.0017(11) -0.0027(11) -0.0033(11) C4B 0.0497(15) 0.0290(13) 0.0465(14) 0.0047(11) -0.0052(11) -0.0043(11) C5B 0.0574(16) 0.0330(13) 0.0437(14) 0.0080(11) -0.0013(12) -0.0101(13) C6B 0.067(2) 0.0480(16) 0.0438(15) 0.0114(13) -0.0079(14) -0.0135(15) C7B 0.0595(19) 0.0469(17) 0.0608(19) 0.0146(15) -0.0148(15) -0.0024(15) C8B 0.0533(16) 0.0358(14) 0.0640(18) 0.0096(13) -0.0067(13) 0.0025(13) C9B 0.0521(16) 0.0302(13) 0.0524(16) 0.0030(12) -0.0031(12) -0.0013(12) C10B 0.0603(17) 0.0342(14) 0.0518(16) -0.0030(12) -0.0004(13) 0.0053(13) C11B 0.0473(15) 0.0329(13) 0.0459(14) -0.0024(11) -0.0055(11) 0.0009(12) O12B 0.0508(10) 0.0360(10) 0.0433(9) 0.0002(8) 0.0029(8) 0.0062(8) C13B 0.0378(13) 0.0353(13) 0.0361(12) 0.0017(10) 0.0010(9) 0.0052(10) C14B 0.0370(13) 0.0360(13) 0.0335(12) 0.0018(10) 0.0010(9) 0.0004(10) O15B 0.0455(10) 0.0371(10) 0.0421(9) 0.0048(8) 0.0058(7) -0.0025(8) C16B 0.0577(16) 0.0321(13) 0.0438(14) -0.0021(11) 0.0024(12) -0.0074(12) C17B 0.073(2) 0.0340(14) 0.0518(16) 0.0048(12) 0.0104(14) -0.0064(14) C18B 0.0622(17) 0.0287(13) 0.0472(15) 0.0000(11) 0.0084(12) 0.0074(12) C19B 0.073(2) 0.0409(15) 0.0477(16) 0.0061(13) 0.0090(14) 0.0135(15) C20B 0.074(2) 0.0508(17) 0.0507(18) -0.0003(14) -0.0006(15) 0.0272(17) C21B 0.0519(17) 0.0495(17) 0.0602(18) -0.0045(15) -0.0016(13) 0.0161(14) C22B 0.0493(15) 0.0372(14) 0.0539(16) -0.0016(12) 0.0061(12) 0.0118(12) C23B 0.0522(15) 0.0313(13) 0.0416(13) -0.0032(10) 0.0052(11) 0.0084(11) C24B 0.0550(16) 0.0276(12) 0.0407(13) -0.0010(10) 0.0054(11) -0.0017(11) N25B 0.0408(11) 0.0310(11) 0.0366(11) 0.0014(8) 0.0022(8) -0.0003(9) C26B 0.0694(19) 0.0388(15) 0.0376(13) 0.0103(11) 0.0030(12) -0.0040(14) C27B 0.089(2) 0.0513(19) 0.0439(16) -0.0041(14) 0.0019(15) -0.0087(18) C28B 0.134(4) 0.0471(19) 0.0455(17) -0.0041(15) 0.011(2) -0.002(2) C29B 0.109(3) 0.058(2) 0.0545(19) 0.0065(17) 0.024(2) 0.012(2) C30B 0.080(2) 0.0545(19) 0.0611(19) 0.0185(16) 0.0220(17) 0.0094(17) C31B 0.074(2) 0.0350(14) 0.0494(16) 0.0084(12) 0.0096(14) -0.0003(14) C32B 0.030(2) 0.050(3) 0.060(3) 0.013(2) 0.003(2) 0.0106(19) C33B 0.041(3) 0.063(3) 0.066(4) 0.011(3) -0.006(2) -0.009(2) C34B 0.043(3) 0.076(4) 0.101(5) 0.029(4) -0.013(3) -0.021(3) C35B 0.042(3) 0.103(5) 0.079(5) 0.041(5) 0.004(2) -0.014(3) C36B 0.056(3) 0.098(6) 0.075(4) 0.036(4) 0.024(3) 0.027(4) C37B 0.048(3) 0.070(4) 0.063(3) 0.013(3) 0.017(3) 0.024(3) S40 0.0465(3) 0.0457(4) 0.0525(4) -0.0023(3) -0.0083(3) 0.0028(3) O41 0.0857(18) 0.0635(15) 0.0702(16) -0.0249(13) -0.0090(13) 0.0054(14) O42 0.0702(14) 0.0422(12) 0.0650(13) -0.0016(10) -0.0127(11) 0.0085(10) O43 0.0482(12) 0.0787(17) 0.0870(17) 0.0192(15) -0.0039(11) -0.0038(13) C40 0.0494(16) 0.0581(18) 0.0414(15) -0.0016(13) 0.0017(12) 0.0073(14) F41 0.0704(11) 0.0509(10) 0.0581(10) -0.0064(8) 0.0025(9) 0.0142(9) F42 0.0899(14) 0.0741(13) 0.0513(10) 0.0118(10) -0.0069(9) 0.0019(12) F43 0.0528(11) 0.0759(14) 0.0903(15) -0.0022(11) 0.0165(10) -0.0044(10) S50 0.0366(6) 0.0362(7) 0.0413(6) 0.0063(6) 0.0048(4) 0.0052(4) O51 0.0527(19) 0.0439(18) 0.094(3) 0.020(2) -0.0201(19) -0.0005(15) O52 0.115(3) 0.0435(19) 0.078(3) -0.0038(17) 0.006(2) -0.013(2) O53 0.076(2) 0.086(3) 0.087(3) 0.040(2) 0.0420(19) 0.028(2) C50 0.060(3) 0.043(3) 0.044(3) -0.0013(18) -0.003(2) 0.002(2) F51 0.071(2) 0.082(2) 0.109(3) 0.041(2) -0.050(2) -0.010(2) F52 0.101(2) 0.0363(14) 0.079(2) -0.0208(14) -0.017(2) 0.0232(15) F53 0.112(3) 0.0554(17) 0.0692(18) 0.0196(14) 0.0421(18) 0.0117(18) _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 C1A N25A 1.333(3) . ? C1A N2A 1.338(3) . ? N2A C13A 1.381(3) . ? N2A C3A 1.474(3) . ? C3A C4A 1.518(4) . ? C3A C11A 1.560(4) . ? C4A C5A 1.392(4) . ? C4A C9A 1.402(4) . ? C5A C6A 1.400(4) . ? C5A C26A 1.483(4) . ? C6A C7A 1.384(5) . ? C7A C8A 1.379(5) . ? C8A C9A 1.380(4) . ? C9A C10A 1.507(5) . ? C10A C11A 1.517(4) . ? C11A O12A 1.479(4) . ? O12A C13A 1.345(3) . ? C13A C14A 1.359(4) . ? C14A O15A 1.340(3) . ? C14A N25A 1.377(3) . ? O15A C16A 1.485(3) . ? C16A C17A 1.504(4) . ? C16A C24A 1.554(4) . ? C17A C18A 1.501(4) . ? C18A C19A 1.379(4) . ? C18A C23A 1.403(4) . ? C19A C20A 1.384(5) . ? C20A C21A 1.394(5) . ? C21A C22A 1.394(4) . ? C22A C23A 1.393(4) . ? C22A C32A 1.494(4) . ? C23A C24A 1.516(4) . ? C24A N25A 1.471(3) . ? C26A C27A 1.392(4) . ? C26A C31A 1.393(4) . ? C27A C28A 1.378(4) . ? C28A C29A 1.382(5) . ? C29A C30A 1.367(6) . ? C30A C31A 1.385(5) . ? C32A C37A 1.383(4) . ? C32A C33A 1.397(4) . ? C33A C34A 1.388(4) . ? C34A C35A 1.372(5) . ? C35A C36A 1.385(5) . ? C36A C37A 1.383(5) . ? C1B N2B 1.330(4) . ? C1B N25B 1.337(3) . ? N2B C13B 1.379(3) . ? N2B C3B 1.481(3) . ? C3B C4B 1.527(4) . ? C3B C11B 1.548(4) . ? C4B C5B 1.393(4) . ? C4B C9B 1.399(4) . ? C5B C6B 1.398(5) . ? C5B C26B 1.484(5) . ? C6B C7B 1.384(5) . ? C7B C8B 1.379(5) . ? C8B C9B 1.383(4) . ? C9B C10B 1.511(4) . ? C10B C11B 1.510(4) . ? C11B O12B 1.481(3) . ? O12B C13B 1.340(3) . ? C13B C14B 1.356(4) . ? C14B O15B 1.338(3) . ? C14B N25B 1.381(3) . ? O15B C16B 1.473(3) . ? C16B C17B 1.509(4) . ? C16B C24B 1.550(4) . ? C17B C18B 1.508(5) . ? C18B C19B 1.378(4) . ? C18B C23B 1.405(4) . ? C19B C20B 1.374(5) . ? C20B C21B 1.389(5) . ? C21B C22B 1.384(4) . ? C22B C23B 1.392(4) . ? C22B C32B 1.484(4) . ? C22B C32" 1.556(8) . ? C23B C24B 1.515(4) . ? C24B N25B 1.482(3) . ? C26B C31B 1.396(5) . ? C26B C27B 1.399(5) . ? C27B C28B 1.388(6) . ? C28B C29B 1.376(7) . ? C29B C30B 1.376(6) . ? C30B C31B 1.391(5) . ? C32B C33B 1.3900 . ? C32B C37B 1.3900 . ? C33B C34B 1.3900 . ? C34B C35B 1.3900 . ? C35B C36B 1.3900 . ? C36B C37B 1.3900 . ? C32" C33" 1.3900 . ? C32" C37" 1.3900 . ? C33" C34" 1.3900 . ? C34" C35" 1.3900 . ? C35" C36" 1.3900 . ? C36" C37" 1.3900 . ? S40 O42 1.428(2) . ? S40 O43 1.434(3) . ? S40 O41 1.438(3) . ? S40 C40 1.821(4) . ? C40 F41 1.324(4) . ? C40 F42 1.325(4) . ? C40 F43 1.336(4) . ? S50 O51 1.399(3) . ? S50 O53 1.415(4) . ? S50 O52 1.441(4) . ? S50 C50 1.819(6) . ? C50 F53 1.316(7) . ? C50 F51 1.316(7) . ? C50 F52 1.331(6) . ? S50' O52' 1.385(7) . ? S50' O53' 1.445(8) . ? S50' O51' 1.468(9) . ? S50' C50' 1.819(12) . ? C50' F51' 1.309(12) . ? C50' F52' 1.314(11) . ? C50' F53' 1.325(11) . ? 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 N25A C1A N2A 105.2(2) . . ? C1A N2A C13A 110.9(2) . . ? C1A N2A C3A 139.0(2) . . ? C13A N2A C3A 109.7(2) . . ? N2A C3A C4A 114.2(2) . . ? N2A C3A C11A 99.2(2) . . ? C4A C3A C11A 103.2(2) . . ? C5A C4A C9A 121.2(3) . . ? C5A C4A C3A 128.9(2) . . ? C9A C4A C3A 109.9(2) . . ? C4A C5A C6A 117.4(3) . . ? C4A C5A C26A 121.3(2) . . ? C6A C5A C26A 121.2(3) . . ? C7A C6A C5A 121.4(3) . . ? C8A C7A C6A 120.5(3) . . ? C7A C8A C9A 119.6(3) . . ? C8A C9A C4A 120.0(3) . . ? C8A C9A C10A 129.2(3) . . ? C4A C9A C10A 110.7(2) . . ? C9A C10A C11A 104.2(2) . . ? O12A C11A C10A 109.2(2) . . ? O12A C11A C3A 104.9(2) . . ? C10A C11A C3A 105.6(2) . . ? C13A O12A C11A 105.87(19) . . ? O12A C13A C14A 140.7(3) . . ? O12A C13A N2A 112.9(2) . . ? C14A C13A N2A 106.4(2) . . ? O15A C14A C13A 140.9(3) . . ? O15A C14A N25A 113.3(2) . . ? C13A C14A N25A 105.8(2) . . ? C14A O15A C16A 105.39(19) . . ? O15A C16A C17A 109.6(2) . . ? O15A C16A C24A 103.9(2) . . ? C17A C16A C24A 106.0(2) . . ? C18A C17A C16A 103.6(2) . . ? C19A C18A C23A 120.0(3) . . ? C19A C18A C17A 129.1(3) . . ? C23A C18A C17A 110.9(2) . . ? C18A C19A C20A 119.7(3) . . ? C19A C20A C21A 120.1(3) . . ? C22A C21A C20A 121.2(3) . . ? C23A C22A C21A 117.9(3) . . ? C23A C22A C32A 121.5(2) . . ? C21A C22A C32A 120.6(2) . . ? C22A C23A C18A 121.0(2) . . ? C22A C23A C24A 129.6(2) . . ? C18A C23A C24A 109.4(2) . . ? N25A C24A C23A 114.2(2) . . ? N25A C24A C16A 99.7(2) . . ? C23A C24A C16A 102.6(2) . . ? C1A N25A C14A 111.7(2) . . ? C1A N25A C24A 139.2(2) . . ? C14A N25A C24A 109.0(2) . . ? C27A C26A C31A 118.1(3) . . ? C27A C26A C5A 120.6(3) . . ? C31A C26A C5A 121.2(3) . . ? C28A C27A C26A 121.3(3) . . ? C27A C28A C29A 119.7(3) . . ? C30A C29A C28A 120.0(3) . . ? C29A C30A C31A 120.7(3) . . ? C30A C31A C26A 120.2(3) . . ? C37A C32A C33A 119.0(3) . . ? C37A C32A C22A 120.8(2) . . ? C33A C32A C22A 120.2(2) . . ? C34A C33A C32A 120.2(3) . . ? C35A C34A C33A 120.1(3) . . ? C34A C35A C36A 120.1(3) . . ? C37A C36A C35A 120.0(3) . . ? C36A C37A C32A 120.6(3) . . ? N2B C1B N25B 105.3(2) . . ? C1B N2B C13B 111.4(2) . . ? C1B N2B C3B 139.6(2) . . ? C13B N2B C3B 109.0(2) . . ? N2B C3B C4B 113.1(2) . . ? N2B C3B C11B 99.8(2) . . ? C4B C3B C11B 102.9(2) . . ? C5B C4B C9B 121.4(3) . . ? C5B C4B C3B 129.3(3) . . ? C9B C4B C3B 109.2(2) . . ? C4B C5B C6B 116.5(3) . . ? C4B C5B C26B 123.4(3) . . ? C6B C5B C26B 120.2(3) . . ? C7B C6B C5B 122.2(3) . . ? C8B C7B C6B 120.5(3) . . ? C7B C8B C9B 118.8(3) . . ? C8B C9B C4B 120.5(3) . . ? C8B C9B C10B 127.9(3) . . ? C4B C9B C10B 111.5(2) . . ? C11B C10B C9B 102.9(2) . . ? O12B C11B C10B 108.1(2) . . ? O12B C11B C3B 104.9(2) . . ? C10B C11B C3B 107.0(2) . . ? C13B O12B C11B 105.7(2) . . ? O12B C13B C14B 140.4(3) . . ? O12B C13B N2B 113.5(2) . . ? C14B C13B N2B 106.1(2) . . ? O15B C14B C13B 140.7(3) . . ? O15B C14B N25B 113.3(2) . . ? C13B C14B N25B 106.0(2) . . ? C14B O15B C16B 106.6(2) . . ? O15B C16B C17B 108.5(2) . . ? O15B C16B C24B 104.5(2) . . ? C17B C16B C24B 106.1(3) . . ? C18B C17B C16B 103.6(2) . . ? C19B C18B C23B 120.0(3) . . ? C19B C18B C17B 129.1(3) . . ? C23B C18B C17B 110.8(3) . . ? C20B C19B C18B 120.0(3) . . ? C19B C20B C21B 119.8(3) . . ? C22B C21B C20B 121.8(3) . . ? C21B C22B C23B 117.9(3) . . ? C21B C22B C32B 119.1(3) . . ? C23B C22B C32B 122.5(3) . . ? C21B C22B C32" 126.7(6) . . ? C23B C22B C32" 115.2(6) . . ? C22B C23B C18B 120.5(3) . . ? C22B C23B C24B 130.1(3) . . ? C18B C23B C24B 109.4(3) . . ? N25B C24B C23B 113.0(2) . . ? N25B C24B C16B 99.7(2) . . ? C23B C24B C16B 103.3(2) . . ? C1B N25B C14B 111.1(2) . . ? C1B N25B C24B 139.8(2) . . ? C14B N25B C24B 108.4(2) . . ? C31B C26B C27B 117.8(3) . . ? C31B C26B C5B 121.1(3) . . ? C27B C26B C5B 121.0(3) . . ? C28B C27B C26B 120.7(4) . . ? C29B C28B C27B 120.5(4) . . ? C28B C29B C30B 120.0(4) . . ? C29B C30B C31B 120.0(4) . . ? C30B C31B C26B 121.1(3) . . ? C33B C32B C37B 120.0 . . ? C33B C32B C22B 120.0(3) . . ? C37B C32B C22B 120.0(3) . . ? C32B C33B C34B 120.0 . . ? C35B C34B C33B 120.0 . . ? C36B C35B C34B 120.0 . . ? C37B C36B C35B 120.0 . . ? C36B C37B C32B 120.0 . . ? C33" C32" C37" 120.0 . . ? C33" C32" C22B 117.5(7) . . ? C37" C32" C22B 122.5(7) . . ? C32" C33" C34" 120.0 . . ? C35" C34" C33" 120.0 . . ? C34" C35" C36" 120.0 . . ? C37" C36" C35" 120.0 . . ? C36" C37" C32" 120.0 . . ? O42 S40 O43 115.27(16) . . ? O42 S40 O41 115.02(16) . . ? O43 S40 O41 116.06(17) . . ? O42 S40 C40 102.45(13) . . ? O43 S40 C40 102.63(16) . . ? O41 S40 C40 102.41(16) . . ? F41 C40 F42 107.5(3) . . ? F41 C40 F43 105.8(3) . . ? F42 C40 F43 108.1(3) . . ? F41 C40 S40 112.0(2) . . ? F42 C40 S40 112.1(2) . . ? F43 C40 S40 111.0(2) . . ? O51 S50 O53 117.9(3) . . ? O51 S50 O52 114.8(3) . . ? O53 S50 O52 111.0(3) . . ? O51 S50 C50 103.3(3) . . ? O53 S50 C50 104.1(3) . . ? O52 S50 C50 103.7(2) . . ? F53 C50 F51 109.8(5) . . ? F53 C50 F52 104.6(5) . . ? F51 C50 F52 106.8(6) . . ? F53 C50 S50 110.9(5) . . ? F51 C50 S50 112.8(4) . . ? F52 C50 S50 111.5(4) . . ? O52' S50' O53' 118.1(5) . . ? O52' S50' O51' 118.0(6) . . ? O53' S50' O51' 109.6(7) . . ? O52' S50' C50' 104.5(5) . . ? O53' S50' C50' 102.5(5) . . ? O51' S50' C50' 101.2(5) . . ? F51' C50' F52' 108.4(10) . . ? F51' C50' F53' 106.7(9) . . ? F52' C50' F53' 104.8(9) . . ? F51' C50' S50' 111.5(8) . . ? F52' C50' S50' 113.4(8) . . ? F53' C50' S50' 111.6(8) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 69.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.277 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.044 #===END