# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Krishnan Ravikumar' _publ_contact_author_address ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabd -500007, India. ; _publ_contact_author_email sshiya@yahoo.com _publ_contact_author_phone 09104027193118 _publ_contact_author_fax 09104027193118 loop_ _publ_author_name _publ_author_address 'N.Jagadeesh Babu' ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabd -500007, India. ; Sridhar ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabd -500007, India. ; B.Sridhar ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabd -500007, India. ; K.Ravikumar ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabd -500007, India. ; data_ah_(hemihydrate) _database_code_depnum_ccdc_archive 'CCDC 849482' #TrackingRef 'web_deposit_cif_file_0_B.Sridhar_1319087400.ahf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Dutasteride hemihydrate' _chemical_melting_point ? _chemical_formula_moiety '2(C27 H30 F6 N2 O2), H2 O' _chemical_formula_sum 'C54 H62 F12 N4 O5' _chemical_formula_weight 1075.08 _chemical_absolute_configuration ad 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 '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 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 8.2124(7) _cell_length_b 18.5162(17) _cell_length_c 34.876(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5303.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 9822 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 20.57 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2248 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51297 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5243 _reflns_number_gt 4559 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.1155P)^2^+1.9302P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5243 _refine_ls_number_parameters 786 _refine_ls_number_restraints 236 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1893 _refine_ls_wR_factor_gt 0.1770 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.148 _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 -0.2212(6) 0.3244(4) 0.22991(14) 0.0592(16) Uani 1 1 d . . . H1A H -0.2865 0.3137 0.2089 0.071 Uiso 1 1 calc R . . C2A C -0.2756(7) 0.3113(4) 0.26470(16) 0.0649(17) Uani 1 1 d . . . H2A H -0.3790 0.2917 0.2678 0.078 Uiso 1 1 calc R . . C3A C -0.1771(6) 0.3270(3) 0.29882(13) 0.0503(13) Uani 1 1 d . . . C5A C 0.0514(6) 0.3209(3) 0.25448(13) 0.0453(12) Uani 1 1 d . . . H5A H 0.0483 0.2686 0.2500 0.054 Uiso 1 1 calc R . . C6A C 0.2260(6) 0.3438(5) 0.25306(14) 0.0672(19) Uani 1 1 d . . . H6A H 0.2867 0.3194 0.2731 0.081 Uiso 1 1 calc R . . H6B H 0.2338 0.3954 0.2574 0.081 Uiso 1 1 calc R . . C7A C 0.2979(6) 0.3250(4) 0.21414(14) 0.0655(18) Uani 1 1 d . . . H7A H 0.3018 0.2729 0.2114 0.079 Uiso 1 1 calc R . . H7B H 0.4086 0.3430 0.2128 0.079 Uiso 1 1 calc R . . C8A C 0.1992(5) 0.3569(3) 0.18096(12) 0.0400(11) Uani 1 1 d . . . H8A H 0.2077 0.4097 0.1822 0.048 Uiso 1 1 calc R . . C9A C 0.0178(5) 0.3362(3) 0.18392(12) 0.0369(10) Uani 1 1 d . . . H9A H 0.0130 0.2834 0.1821 0.044 Uiso 1 1 calc R . . C10A C -0.0541(5) 0.3565(3) 0.22366(12) 0.0382(10) Uani 1 1 d . . . C11A C -0.0797(6) 0.3653(3) 0.15001(13) 0.0482(13) Uani 1 1 d . . . H11A H -0.0858 0.4175 0.1520 0.058 Uiso 1 1 calc R . . H11B H -0.1898 0.3466 0.1514 0.058 Uiso 1 1 calc R . . C12A C -0.0058(6) 0.3453(3) 0.11100(12) 0.0426(11) Uani 1 1 d . . . H12A H -0.0155 0.2936 0.1071 0.051 Uiso 1 1 calc R . . H12B H -0.0666 0.3692 0.0908 0.051 Uiso 1 1 calc R . . C13A C 0.1719(5) 0.3668(3) 0.10828(12) 0.0346(10) Uani 1 1 d . . . C14A C 0.2629(5) 0.3321(3) 0.14216(12) 0.0383(10) Uani 1 1 d . . . H14A H 0.2418 0.2800 0.1407 0.046 Uiso 1 1 calc R . . C15A C 0.4434(6) 0.3426(4) 0.13248(15) 0.0610(16) Uani 1 1 d . . . H15A H 0.5097 0.3055 0.1444 0.073 Uiso 1 1 calc R . . H15B H 0.4813 0.3896 0.1408 0.073 Uiso 1 1 calc R . . C16A C 0.4485(6) 0.3362(4) 0.08830(14) 0.0532(13) Uani 1 1 d . . . H16A H 0.5022 0.3778 0.0772 0.064 Uiso 1 1 calc R . . H16B H 0.5071 0.2930 0.0807 0.064 Uiso 1 1 calc R . . C17A C 0.2701(6) 0.3322(3) 0.07498(12) 0.0392(10) Uani 1 1 d . . . H17A H 0.2392 0.2812 0.0731 0.047 Uiso 1 1 calc R . . C18A C 0.1902(8) 0.4492(3) 0.10654(15) 0.0529(13) Uani 1 1 d . . . H18A H 0.1365 0.4706 0.1282 0.079 Uiso 1 1 calc R . . H18B H 0.1418 0.4670 0.0833 0.079 Uiso 1 1 calc R . . H18C H 0.3036 0.4617 0.1070 0.079 Uiso 1 1 calc R . . C19A C -0.0676(9) 0.4379(3) 0.22855(16) 0.0713(19) Uani 1 1 d . . . H19A H -0.1028 0.4488 0.2542 0.107 Uiso 1 1 calc R . . H19B H -0.1452 0.4567 0.2105 0.107 Uiso 1 1 calc R . . H19C H 0.0368 0.4597 0.2241 0.107 Uiso 1 1 calc R . . C20A C 0.2439(6) 0.3672(3) 0.03594(12) 0.0405(11) Uani 1 1 d . . . C22A C 0.0600(6) 0.3584(3) -0.02038(13) 0.0407(11) Uani 1 1 d . . . C23A C -0.1039(6) 0.3576(3) -0.03172(14) 0.0444(11) Uani 1 1 d . . . C24A C -0.1470(8) 0.3693(3) -0.06971(16) 0.0617(15) Uani 1 1 d . . . H24A H -0.2563 0.3702 -0.0767 0.074 Uiso 1 1 calc R . . C25A C -0.0287(9) 0.3795(4) -0.09707(16) 0.0684(17) Uani 1 1 d . . . H25A H -0.0572 0.3869 -0.1226 0.082 Uiso 1 1 calc R . . C26A C 0.1338(8) 0.3787(4) -0.08616(15) 0.0604(15) Uani 1 1 d . A . C27A C 0.1781(7) 0.3694(3) -0.04808(14) 0.0518(13) Uani 1 1 d . . . H27A H 0.2875 0.3705 -0.0412 0.062 Uiso 1 1 calc R . . C28A C -0.2366(7) 0.3454(3) -0.00279(16) 0.0518(13) Uani 1 1 d . . . C29A C 0.2635(10) 0.3863(5) -0.11592(17) 0.094(2) Uani 1 1 d DU . . F1A F -0.2103(4) 0.28589(18) 0.01815(10) 0.0662(9) Uani 1 1 d . . . F2A F -0.2484(5) 0.3992(2) 0.02191(11) 0.0751(11) Uani 1 1 d . . . F3A F -0.3813(4) 0.3365(2) -0.01918(11) 0.0769(11) Uani 1 1 d . . . F4A F 0.4112(15) 0.3932(8) -0.1020(4) 0.103(3) Uani 0.498(9) 1 d PDU A 1 F5A F 0.2635(16) 0.3272(6) -0.1391(3) 0.104(3) Uani 0.498(9) 1 d PDU A 1 F6A F 0.2407(16) 0.4402(6) -0.1395(3) 0.113(3) Uani 0.498(9) 1 d PDU A 1 F41 F 0.4061(14) 0.3575(7) -0.1053(3) 0.098(3) Uani 0.502(9) 1 d PDU A 2 F51 F 0.2215(15) 0.3627(8) -0.1491(2) 0.110(3) Uani 0.502(9) 1 d PDU A 2 F61 F 0.3032(15) 0.4570(5) -0.1217(3) 0.109(3) Uani 0.502(9) 1 d PDU A 2 N4A N -0.0197(5) 0.3343(3) 0.29221(11) 0.0491(11) Uani 1 1 d D . . H3N H 0.044(5) 0.339(3) 0.3101(11) 0.044(15) Uiso 1 1 d D . . N21A N 0.1049(5) 0.3446(3) 0.01771(11) 0.0435(10) Uani 1 1 d D . . H4N H 0.056(9) 0.313(3) 0.030(2) 0.10(3) Uiso 1 1 d D . . O1A O -0.2392(5) 0.3360(3) 0.33103(10) 0.0666(12) Uani 1 1 d . . . O2A O 0.3340(5) 0.4101(2) 0.02168(10) 0.0641(12) Uani 1 1 d . . . C1B C 0.1693(6) 0.3756(4) 0.45938(14) 0.0581(16) Uani 1 1 d . . . H1B H 0.2396 0.3740 0.4803 0.070 Uiso 1 1 calc R . . C2B C 0.2273(7) 0.3621(4) 0.42493(16) 0.0637(17) Uani 1 1 d . . . H2B H 0.3369 0.3505 0.4223 0.076 Uiso 1 1 calc R . . C3B C 0.1256(6) 0.3648(3) 0.39078(14) 0.0473(12) Uani 1 1 d . . . C5B C -0.1015(6) 0.3514(3) 0.43484(13) 0.0411(11) Uani 1 1 d . . . H5B H -0.0844 0.2999 0.4399 0.049 Uiso 1 1 calc R . . C6B C -0.2833(6) 0.3647(4) 0.43650(13) 0.0554(15) Uani 1 1 d . . . H6C H -0.3377 0.3363 0.4169 0.066 Uiso 1 1 calc R . . H6D H -0.3057 0.4153 0.4316 0.066 Uiso 1 1 calc R . . C7B C -0.3471(6) 0.3438(4) 0.47591(13) 0.0562(15) Uani 1 1 d . . . H7C H -0.4614 0.3566 0.4775 0.067 Uiso 1 1 calc R . . H7D H -0.3391 0.2918 0.4788 0.067 Uiso 1 1 calc R . . C8B C -0.2569(6) 0.3795(3) 0.50881(12) 0.0396(10) Uani 1 1 d . . . H8B H -0.2764 0.4317 0.5076 0.047 Uiso 1 1 calc R . . C9B C -0.0719(5) 0.3659(3) 0.50524(12) 0.0388(10) Uani 1 1 d . . . H9B H -0.0574 0.3134 0.5051 0.047 Uiso 1 1 calc R . . C10B C -0.0080(6) 0.3936(3) 0.46608(13) 0.0384(10) Uani 1 1 d . . . C11B C 0.0237(7) 0.3944(4) 0.54004(13) 0.0556(14) Uani 1 1 d . . . H11C H 0.1367 0.3798 0.5377 0.067 Uiso 1 1 calc R . . H11D H 0.0204 0.4468 0.5399 0.067 Uiso 1 1 calc R . . C12B C -0.0439(6) 0.3668(3) 0.57841(13) 0.0512(13) Uani 1 1 d . . . H12C H -0.0297 0.3148 0.5799 0.061 Uiso 1 1 calc R . . H12D H 0.0160 0.3886 0.5994 0.061 Uiso 1 1 calc R . . C13B C -0.2247(6) 0.3854(3) 0.58211(12) 0.0391(10) Uani 1 1 d . . . C14B C -0.3144(5) 0.3520(3) 0.54751(13) 0.0370(10) Uani 1 1 d . . . H14B H -0.2909 0.3001 0.5480 0.044 Uiso 1 1 calc R . . C15B C -0.4957(6) 0.3603(3) 0.55823(14) 0.0480(12) Uani 1 1 d . . . H15C H -0.5352 0.4082 0.5518 0.058 Uiso 1 1 calc R . . H15D H -0.5618 0.3246 0.5451 0.058 Uiso 1 1 calc R . . C16B C -0.4984(7) 0.3483(3) 0.60179(14) 0.0508(13) Uani 1 1 d . . . H16C H -0.5508 0.3028 0.6079 0.061 Uiso 1 1 calc R . . H16D H -0.5576 0.3869 0.6144 0.061 Uiso 1 1 calc R . . C17B C -0.3184(6) 0.3475(3) 0.61523(13) 0.0418(11) Uani 1 1 d . . . H17B H -0.2819 0.2972 0.6167 0.050 Uiso 1 1 calc R . . C18B C -0.2483(8) 0.4669(3) 0.58514(15) 0.0542(13) Uani 1 1 d . . . H18D H -0.3618 0.4774 0.5887 0.081 Uiso 1 1 calc R . . H18E H -0.2103 0.4895 0.5621 0.081 Uiso 1 1 calc R . . H18F H -0.1876 0.4849 0.6066 0.081 Uiso 1 1 calc R . . C19B C -0.0265(8) 0.4753(3) 0.46131(15) 0.0590(15) Uani 1 1 d . . . H19D H 0.0516 0.4995 0.4773 0.089 Uiso 1 1 calc R . . H19E H -0.1344 0.4895 0.4687 0.089 Uiso 1 1 calc R . . H19F H -0.0081 0.4881 0.4350 0.089 Uiso 1 1 calc R . . C20B C -0.2966(7) 0.3822(3) 0.65464(13) 0.0439(11) Uani 1 1 d . . . C22B C -0.1396(7) 0.3778(3) 0.71340(13) 0.0488(13) Uani 1 1 d . . . C23B C 0.0169(9) 0.3966(4) 0.72462(15) 0.0640(17) Uani 1 1 d . A . C24B C 0.0442(10) 0.4207(5) 0.76161(18) 0.090(3) Uani 1 1 d . . . H24B H 0.1491 0.4338 0.7689 0.107 Uiso 1 1 calc R . . C25B C -0.0803(11) 0.4258(5) 0.78782(18) 0.093(3) Uani 1 1 d . . . H25B H -0.0603 0.4419 0.8126 0.111 Uiso 1 1 calc R . . C26B C -0.2346(9) 0.4066(4) 0.77668(15) 0.0642(17) Uani 1 1 d . A . C27B C -0.2646(8) 0.3829(3) 0.73957(14) 0.0526(13) Uani 1 1 d . . . H27B H -0.3699 0.3705 0.7323 0.063 Uiso 1 1 calc R . . C28B C 0.1576(9) 0.3969(5) 0.69677(19) 0.0870(18) Uani 1 1 d DU . . C29B C -0.3675(11) 0.4094(5) 0.80567(18) 0.0893(19) Uani 1 1 d DU . . F1B F 0.163(2) 0.3358(6) 0.6740(5) 0.085(3) Uani 0.498(9) 1 d PDU A 1 F2B F 0.1634(16) 0.4503(6) 0.6734(4) 0.103(3) Uani 0.498(9) 1 d PDU A 1 F3B F 0.3040(14) 0.3937(8) 0.7151(3) 0.101(3) Uani 0.498(9) 1 d PDU A 1 F12 F 0.190(2) 0.3367(5) 0.6832(5) 0.091(3) Uani 0.502(9) 1 d PDU A 2 F22 F 0.1081(14) 0.4404(6) 0.6658(3) 0.096(3) Uani 0.502(9) 1 d PDU A 2 F32 F 0.2852(16) 0.4312(7) 0.7102(3) 0.102(3) Uani 0.502(9) 1 d PDU A 2 F4B F -0.3446(15) 0.4711(5) 0.8280(3) 0.100(3) Uani 0.498(9) 1 d PDU A 1 F5B F -0.363(2) 0.3570(5) 0.8287(4) 0.097(3) Uani 0.498(9) 1 d PDU A 1 F6B F -0.5089(13) 0.4204(8) 0.7913(3) 0.101(3) Uani 0.498(9) 1 d PDU A 1 F42 F -0.4185(18) 0.4728(5) 0.8158(3) 0.110(3) Uani 0.502(9) 1 d PDU A 2 F52 F -0.329(2) 0.3740(7) 0.8379(4) 0.094(3) Uani 0.502(9) 1 d PDU A 2 F62 F -0.5046(12) 0.3757(7) 0.7932(3) 0.098(3) Uani 0.502(9) 1 d PDU A 2 N4B N -0.0345(5) 0.3662(3) 0.39706(11) 0.0475(11) Uani 1 1 d . . . H1N H -0.088(6) 0.367(2) 0.3768(14) 0.028(12) Uiso 1 1 d . . . N21B N -0.1736(6) 0.3541(3) 0.67559(12) 0.0459(10) Uani 1 1 d . . . H2N H -0.127(5) 0.318(2) 0.6680(12) 0.015(10) Uiso 1 1 d . . . O1B O 0.1837(5) 0.3665(3) 0.35788(10) 0.0626(11) Uani 1 1 d . . . O2B O -0.3807(6) 0.4311(2) 0.66555(10) 0.0644(12) Uani 1 1 d . . . O1W O 0.4602(5) 0.2795(2) 0.34890(15) 0.0736(13) Uani 1 1 d D . . H1W H 0.543(5) 0.308(3) 0.3424(18) 0.07(2) Uiso 1 1 d D . . H2W H 0.376(5) 0.308(3) 0.353(2) 0.10(3) Uiso 1 1 d 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 C1A 0.033(3) 0.113(5) 0.031(3) 0.003(3) 0.000(2) -0.008(3) C2A 0.035(3) 0.120(5) 0.040(3) 0.002(3) 0.006(2) -0.018(3) C3A 0.035(3) 0.086(4) 0.030(2) 0.004(2) 0.005(2) -0.012(3) C5A 0.038(3) 0.074(3) 0.024(2) 0.003(2) 0.002(2) 0.000(2) C6A 0.031(3) 0.145(6) 0.025(2) 0.007(3) -0.004(2) -0.003(3) C7A 0.026(2) 0.136(6) 0.034(3) 0.008(3) -0.001(2) 0.008(3) C8A 0.028(2) 0.067(3) 0.025(2) 0.001(2) 0.0003(18) -0.001(2) C9A 0.032(2) 0.054(3) 0.025(2) 0.0032(19) -0.0016(18) 0.000(2) C10A 0.032(2) 0.058(3) 0.024(2) 0.0043(19) 0.0019(18) 0.003(2) C11A 0.029(2) 0.084(4) 0.031(2) 0.007(2) 0.0006(19) 0.006(2) C12A 0.034(2) 0.067(3) 0.027(2) 0.004(2) -0.0003(19) 0.000(2) C13A 0.032(2) 0.046(2) 0.026(2) 0.0011(18) 0.0046(18) 0.005(2) C14A 0.030(2) 0.056(3) 0.029(2) 0.002(2) 0.0001(18) 0.005(2) C15A 0.031(3) 0.112(5) 0.039(3) 0.008(3) 0.006(2) 0.003(3) C16A 0.036(3) 0.086(4) 0.037(3) 0.002(3) 0.009(2) 0.009(3) C17A 0.039(2) 0.052(3) 0.026(2) -0.0006(19) 0.0067(19) 0.005(2) C18A 0.061(3) 0.057(3) 0.041(3) -0.002(2) 0.012(3) 0.000(3) C19A 0.097(5) 0.074(4) 0.043(3) 0.001(3) 0.030(3) 0.018(4) C20A 0.042(3) 0.054(3) 0.026(2) -0.003(2) 0.009(2) 0.000(2) C22A 0.047(3) 0.046(3) 0.028(2) -0.0037(19) 0.006(2) 0.000(2) C23A 0.048(3) 0.047(3) 0.039(3) -0.005(2) 0.000(2) 0.001(2) C24A 0.062(4) 0.072(4) 0.051(3) 0.009(3) -0.009(3) 0.008(3) C25A 0.075(4) 0.094(5) 0.036(3) 0.013(3) -0.007(3) -0.002(4) C26A 0.070(4) 0.075(4) 0.036(3) 0.011(3) 0.002(3) -0.007(3) C27A 0.049(3) 0.073(3) 0.034(2) 0.001(2) 0.004(2) -0.007(3) C28A 0.043(3) 0.060(3) 0.052(3) -0.007(3) -0.001(2) -0.002(3) C29A 0.098(4) 0.148(5) 0.036(3) 0.003(3) 0.017(3) -0.023(4) F1A 0.057(2) 0.071(2) 0.070(2) 0.0146(17) 0.0070(17) -0.0110(16) F2A 0.077(2) 0.080(2) 0.069(2) -0.0293(19) 0.0219(19) -0.004(2) F3A 0.0406(17) 0.114(3) 0.076(2) -0.007(2) 0.0003(17) 0.0036(19) F4A 0.090(5) 0.161(7) 0.058(4) -0.009(5) 0.019(4) -0.043(6) F5A 0.116(6) 0.145(7) 0.051(5) -0.019(5) 0.023(5) -0.016(6) F6A 0.129(6) 0.154(6) 0.057(5) 0.037(5) 0.022(4) -0.026(6) F41 0.083(5) 0.151(8) 0.059(4) 0.004(6) 0.034(4) -0.002(6) F51 0.121(6) 0.169(7) 0.039(4) -0.003(5) 0.017(4) -0.026(6) F61 0.114(6) 0.146(6) 0.066(5) 0.017(5) 0.023(4) -0.039(5) N4A 0.034(2) 0.089(3) 0.0246(19) -0.001(2) -0.0010(17) -0.008(2) N21A 0.043(2) 0.059(3) 0.0280(19) 0.0033(18) 0.0060(17) -0.008(2) O1A 0.042(2) 0.126(4) 0.0315(18) 0.000(2) 0.0109(16) -0.022(2) O2A 0.063(3) 0.090(3) 0.0392(19) 0.0117(19) 0.0022(19) -0.030(2) C1B 0.033(3) 0.111(5) 0.031(3) -0.002(3) -0.005(2) -0.007(3) C2B 0.031(3) 0.115(5) 0.045(3) -0.010(3) 0.002(2) 0.002(3) C3B 0.037(3) 0.072(4) 0.033(2) -0.012(2) 0.004(2) 0.004(2) C5B 0.036(2) 0.058(3) 0.029(2) -0.008(2) -0.0032(19) 0.002(2) C6B 0.035(3) 0.100(4) 0.031(2) -0.011(3) -0.006(2) -0.006(3) C7B 0.035(3) 0.102(4) 0.031(2) -0.008(3) -0.002(2) -0.012(3) C8B 0.032(2) 0.057(3) 0.030(2) -0.004(2) -0.0011(19) 0.005(2) C9B 0.031(2) 0.052(3) 0.033(2) -0.004(2) -0.0018(19) 0.003(2) C10B 0.029(2) 0.054(3) 0.032(2) -0.006(2) -0.0024(19) 0.003(2) C11B 0.035(3) 0.099(4) 0.033(3) -0.007(3) -0.005(2) -0.002(3) C12B 0.038(3) 0.086(4) 0.029(2) -0.005(2) -0.009(2) 0.005(3) C13B 0.037(2) 0.054(3) 0.026(2) -0.0013(19) 0.0023(19) 0.007(2) C14B 0.032(2) 0.043(2) 0.036(2) -0.0016(19) -0.0002(19) 0.003(2) C15B 0.040(3) 0.061(3) 0.043(3) 0.001(2) 0.001(2) -0.005(2) C16B 0.050(3) 0.063(3) 0.040(3) -0.006(2) 0.008(2) -0.002(3) C17B 0.048(3) 0.043(3) 0.034(2) -0.002(2) 0.008(2) 0.010(2) C18B 0.071(4) 0.048(3) 0.044(3) 0.001(2) -0.002(3) -0.003(3) C19B 0.074(4) 0.060(3) 0.042(3) -0.007(2) 0.010(3) -0.015(3) C20B 0.053(3) 0.048(3) 0.031(2) 0.002(2) 0.005(2) 0.002(2) C22B 0.062(3) 0.057(3) 0.028(2) 0.010(2) 0.003(2) -0.004(3) C23B 0.070(4) 0.083(4) 0.039(3) 0.007(3) -0.007(3) -0.025(3) C24B 0.081(5) 0.141(7) 0.046(3) -0.005(4) -0.003(3) -0.036(5) C25B 0.106(6) 0.139(7) 0.033(3) -0.002(4) -0.005(4) -0.017(6) C26B 0.082(4) 0.079(4) 0.031(3) 0.012(3) 0.004(3) 0.000(4) C27B 0.060(3) 0.064(3) 0.033(2) 0.013(2) 0.000(2) 0.004(3) C28B 0.071(4) 0.127(4) 0.062(3) -0.005(3) 0.010(3) -0.049(4) C29B 0.100(4) 0.126(4) 0.042(3) 0.009(3) 0.017(3) 0.013(4) F1B 0.052(6) 0.132(5) 0.071(7) -0.023(4) 0.005(4) -0.032(4) F2B 0.092(6) 0.129(6) 0.088(5) 0.011(5) 0.022(5) -0.064(5) F3B 0.066(5) 0.152(8) 0.084(5) -0.002(6) 0.001(4) -0.045(6) F12 0.058(6) 0.131(6) 0.084(8) -0.016(5) 0.013(5) -0.019(5) F22 0.089(6) 0.131(6) 0.069(5) 0.009(5) 0.014(4) -0.076(5) F32 0.083(5) 0.134(7) 0.088(5) -0.008(5) 0.015(4) -0.066(5) F4B 0.100(7) 0.125(5) 0.074(6) -0.026(5) 0.010(5) 0.018(5) F5B 0.117(7) 0.116(6) 0.059(7) 0.020(5) 0.030(5) 0.001(6) F6B 0.091(5) 0.152(7) 0.059(4) 0.009(5) 0.018(4) 0.018(6) F42 0.124(7) 0.129(5) 0.077(6) 0.000(5) 0.023(5) 0.031(5) F52 0.109(6) 0.142(7) 0.032(5) 0.021(5) 0.010(4) 0.000(6) F62 0.083(5) 0.157(7) 0.055(4) 0.002(6) 0.020(4) 0.016(6) N4B 0.038(2) 0.080(3) 0.025(2) -0.011(2) -0.0040(18) 0.000(2) N21B 0.049(2) 0.049(3) 0.039(2) -0.0031(19) -0.0001(19) 0.005(2) O1B 0.044(2) 0.112(3) 0.0321(18) -0.007(2) 0.0082(16) 0.003(2) O2B 0.086(3) 0.069(2) 0.0376(19) -0.0105(18) -0.001(2) 0.032(2) O1W 0.045(2) 0.071(3) 0.105(4) -0.013(2) 0.029(2) -0.016(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 C1A C2A 1.315(7) . ? C1A C10A 1.511(7) . ? C1A H1A 0.9300 . ? C2A C3A 1.468(7) . ? C2A H2A 0.9300 . ? C3A O1A 1.245(6) . ? C3A N4A 1.321(7) . ? C5A N4A 1.461(6) . ? C5A C6A 1.496(7) . ? C5A C10A 1.530(6) . ? C5A H5A 0.9800 . ? C6A C7A 1.521(7) . ? C6A H6A 0.9700 . ? C6A H6B 0.9700 . ? C7A C8A 1.532(7) . ? C7A H7A 0.9700 . ? C7A H7B 0.9700 . ? C8A C14A 1.522(6) . ? C8A C9A 1.542(6) . ? C8A H8A 0.9800 . ? C9A C11A 1.527(6) . ? C9A C10A 1.553(6) . ? C9A H9A 0.9800 . ? C10A C19A 1.522(8) . ? C11A C12A 1.535(6) . ? C11A H11A 0.9700 . ? C11A H11B 0.9700 . ? C12A C13A 1.516(7) . ? C12A H12A 0.9700 . ? C12A H12B 0.9700 . ? C13A C18A 1.535(7) . ? C13A C14A 1.539(6) . ? C13A C17A 1.553(6) . ? C14A C15A 1.532(7) . ? C14A H14A 0.9800 . ? C15A C16A 1.546(7) . ? C15A H15A 0.9700 . ? C15A H15B 0.9700 . ? C16A C17A 1.538(7) . ? C16A H16A 0.9700 . ? C16A H16B 0.9700 . ? C17A C20A 1.523(6) . ? C17A H17A 0.9800 . ? C18A H18A 0.9600 . ? C18A H18B 0.9600 . ? C18A H18C 0.9600 . ? C19A H19A 0.9600 . ? C19A H19B 0.9600 . ? C19A H19C 0.9600 . ? C20A O2A 1.194(6) . ? C20A N21A 1.373(7) . ? C22A C27A 1.384(7) . ? C22A N21A 1.402(6) . ? C22A C23A 1.403(7) . ? C23A C24A 1.388(7) . ? C23A C28A 1.502(8) . ? C24A C25A 1.375(9) . ? C24A H24A 0.9300 . ? C25A C26A 1.388(10) . ? C25A H25A 0.9300 . ? C26A C27A 1.388(7) . ? C26A C29A 1.493(9) . ? C27A H27A 0.9300 . ? C28A F2A 1.320(6) . ? C28A F3A 1.329(7) . ? C28A F1A 1.339(7) . ? C29A F51 1.284(9) . ? C29A F6A 1.306(10) . ? C29A F4A 1.313(11) . ? C29A F41 1.339(11) . ? C29A F5A 1.360(10) . ? C29A F61 1.363(10) . ? N4A H3N 0.82(2) . ? N21A H4N 0.83(2) . ? C1B C2B 1.316(7) . ? C1B C10B 1.512(7) . ? C1B H1B 0.9300 . ? C2B C3B 1.456(7) . ? C2B H2B 0.9300 . ? C3B O1B 1.243(6) . ? C3B N4B 1.334(7) . ? C5B N4B 1.454(6) . ? C5B C6B 1.514(7) . ? C5B C10B 1.546(6) . ? C5B H5B 0.9800 . ? C6B C7B 1.521(7) . ? C6B H6C 0.9700 . ? C6B H6D 0.9700 . ? C7B C8B 1.518(7) . ? C7B H7C 0.9700 . ? C7B H7D 0.9700 . ? C8B C14B 1.518(6) . ? C8B C9B 1.545(6) . ? C8B H8B 0.9800 . ? C9B C11B 1.540(6) . ? C9B C10B 1.550(6) . ? C9B H9B 0.9800 . ? C10B C19B 1.529(7) . ? C11B C12B 1.537(7) . ? C11B H11C 0.9700 . ? C11B H11D 0.9700 . ? C12B C13B 1.530(7) . ? C12B H12C 0.9700 . ? C12B H12D 0.9700 . ? C13B C18B 1.525(7) . ? C13B C14B 1.543(6) . ? C13B C17B 1.555(7) . ? C14B C15B 1.542(7) . ? C14B H14B 0.9800 . ? C15B C16B 1.535(7) . ? C15B H15C 0.9700 . ? C15B H15D 0.9700 . ? C16B C17B 1.551(8) . ? C16B H16C 0.9700 . ? C16B H16D 0.9700 . ? C17B C20B 1.528(6) . ? C17B H17B 0.9800 . ? C18B H18D 0.9600 . ? C18B H18E 0.9600 . ? C18B H18F 0.9600 . ? C19B H19D 0.9600 . ? C19B H19E 0.9600 . ? C19B H19F 0.9600 . ? C20B O2B 1.201(6) . ? C20B N21B 1.351(7) . ? C22B C27B 1.377(8) . ? C22B C23B 1.388(9) . ? C22B N21B 1.417(7) . ? C23B C24B 1.384(9) . ? C23B C28B 1.509(10) . ? C24B C25B 1.375(11) . ? C24B H24B 0.9300 . ? C25B C26B 1.373(11) . ? C25B H25B 0.9300 . ? C26B C27B 1.388(8) . ? C26B C29B 1.488(10) . ? C27B H27B 0.9300 . ? C28B F12 1.241(13) . ? C28B F2B 1.283(11) . ? C28B F32 1.311(10) . ? C28B F3B 1.363(11) . ? C28B F1B 1.383(12) . ? C28B F22 1.406(12) . ? C29B F5B 1.259(13) . ? C29B F6B 1.282(12) . ? C29B F42 1.296(10) . ? C29B F52 1.339(10) . ? C29B F62 1.358(10) . ? C29B F4B 1.395(11) . ? N4B H1N 0.83(5) . ? N21B H2N 0.82(4) . ? O1W H1W 0.89(2) . ? O1W H2W 0.89(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 C2A C1A C10A 120.9(5) . . ? C2A C1A H1A 119.6 . . ? C10A C1A H1A 119.6 . . ? C1A C2A C3A 121.7(5) . . ? C1A C2A H2A 119.2 . . ? C3A C2A H2A 119.2 . . ? O1A C3A N4A 123.0(5) . . ? O1A C3A C2A 122.2(5) . . ? N4A C3A C2A 114.7(4) . . ? N4A C5A C6A 111.4(4) . . ? N4A C5A C10A 109.5(4) . . ? C6A C5A C10A 113.5(4) . . ? N4A C5A H5A 107.4 . . ? C6A C5A H5A 107.4 . . ? C10A C5A H5A 107.4 . . ? C5A C6A C7A 109.7(5) . . ? C5A C6A H6A 109.7 . . ? C7A C6A H6A 109.7 . . ? C5A C6A H6B 109.7 . . ? C7A C6A H6B 109.7 . . ? H6A C6A H6B 108.2 . . ? C6A C7A C8A 112.4(5) . . ? C6A C7A H7A 109.1 . . ? C8A C7A H7A 109.1 . . ? C6A C7A H7B 109.1 . . ? C8A C7A H7B 109.1 . . ? H7A C7A H7B 107.9 . . ? C14A C8A C7A 111.9(4) . . ? C14A C8A C9A 108.5(4) . . ? C7A C8A C9A 111.4(4) . . ? C14A C8A H8A 108.3 . . ? C7A C8A H8A 108.3 . . ? C9A C8A H8A 108.3 . . ? C11A C9A C8A 111.5(4) . . ? C11A C9A C10A 114.0(4) . . ? C8A C9A C10A 111.5(4) . . ? C11A C9A H9A 106.4 . . ? C8A C9A H9A 106.4 . . ? C10A C9A H9A 106.4 . . ? C1A C10A C19A 107.9(5) . . ? C1A C10A C5A 104.1(4) . . ? C19A C10A C5A 112.9(5) . . ? C1A C10A C9A 112.3(4) . . ? C19A C10A C9A 111.6(4) . . ? C5A C10A C9A 107.9(4) . . ? C9A C11A C12A 113.2(4) . . ? C9A C11A H11A 108.9 . . ? C12A C11A H11A 108.9 . . ? C9A C11A H11B 108.9 . . ? C12A C11A H11B 108.9 . . ? H11A C11A H11B 107.8 . . ? C13A C12A C11A 111.8(4) . . ? C13A C12A H12A 109.2 . . ? C11A C12A H12A 109.2 . . ? C13A C12A H12B 109.2 . . ? C11A C12A H12B 109.2 . . ? H12A C12A H12B 107.9 . . ? C12A C13A C18A 111.0(4) . . ? C12A C13A C14A 108.0(4) . . ? C18A C13A C14A 113.5(4) . . ? C12A C13A C17A 116.0(4) . . ? C18A C13A C17A 109.3(4) . . ? C14A C13A C17A 98.6(3) . . ? C8A C14A C15A 119.3(4) . . ? C8A C14A C13A 112.9(4) . . ? C15A C14A C13A 104.3(4) . . ? C8A C14A H14A 106.5 . . ? C15A C14A H14A 106.5 . . ? C13A C14A H14A 106.5 . . ? C14A C15A C16A 103.7(4) . . ? C14A C15A H15A 111.0 . . ? C16A C15A H15A 111.0 . . ? C14A C15A H15B 111.0 . . ? C16A C15A H15B 111.0 . . ? H15A C15A H15B 109.0 . . ? C17A C16A C15A 106.2(4) . . ? C17A C16A H16A 110.5 . . ? C15A C16A H16A 110.5 . . ? C17A C16A H16B 110.5 . . ? C15A C16A H16B 110.5 . . ? H16A C16A H16B 108.7 . . ? C20A C17A C16A 112.6(4) . . ? C20A C17A C13A 114.8(4) . . ? C16A C17A C13A 104.4(4) . . ? C20A C17A H17A 108.3 . . ? C16A C17A H17A 108.3 . . ? C13A C17A H17A 108.3 . . ? C13A C18A H18A 109.5 . . ? C13A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C13A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C10A C19A H19A 109.5 . . ? C10A C19A H19B 109.5 . . ? H19A C19A H19B 109.5 . . ? C10A C19A H19C 109.5 . . ? H19A C19A H19C 109.5 . . ? H19B C19A H19C 109.5 . . ? O2A C20A N21A 121.7(4) . . ? O2A C20A C17A 124.6(5) . . ? N21A C20A C17A 113.7(4) . . ? C27A C22A N21A 120.2(5) . . ? C27A C22A C23A 118.5(4) . . ? N21A C22A C23A 121.2(4) . . ? C24A C23A C22A 120.8(5) . . ? C24A C23A C28A 118.6(5) . . ? C22A C23A C28A 120.5(4) . . ? C25A C24A C23A 120.2(6) . . ? C25A C24A H24A 119.9 . . ? C23A C24A H24A 119.9 . . ? C24A C25A C26A 119.2(5) . . ? C24A C25A H25A 120.4 . . ? C26A C25A H25A 120.4 . . ? C25A C26A C27A 121.1(5) . . ? C25A C26A C29A 119.6(5) . . ? C27A C26A C29A 119.3(6) . . ? C22A C27A C26A 120.2(5) . . ? C22A C27A H27A 119.9 . . ? C26A C27A H27A 119.9 . . ? F2A C28A F3A 108.0(5) . . ? F2A C28A F1A 106.1(4) . . ? F3A C28A F1A 106.0(5) . . ? F2A C28A C23A 112.2(4) . . ? F3A C28A C23A 112.2(4) . . ? F1A C28A C23A 111.9(4) . . ? F51 C29A F6A 69.8(8) . . ? F51 C29A F4A 128.0(11) . . ? F6A C29A F4A 107.0(9) . . ? F51 C29A F41 110.5(9) . . ? F6A C29A F41 127.2(10) . . ? F6A C29A F5A 104.0(7) . . ? F4A C29A F5A 107.3(9) . . ? F41 C29A F5A 81.0(9) . . ? F51 C29A F61 105.0(7) . . ? F4A C29A F61 75.0(9) . . ? F41 C29A F61 102.3(8) . . ? F5A C29A F61 133.2(8) . . ? F51 C29A C26A 113.8(8) . . ? F6A C29A C26A 114.0(8) . . ? F4A C29A C26A 114.2(8) . . ? F41 C29A C26A 113.1(7) . . ? F5A C29A C26A 109.7(8) . . ? F61 C29A C26A 111.3(8) . . ? C3A N4A C5A 122.1(4) . . ? C3A N4A H3N 120(4) . . ? C5A N4A H3N 116(4) . . ? C20A N21A C22A 127.0(4) . . ? C20A N21A H4N 112(6) . . ? C22A N21A H4N 119(6) . . ? C2B C1B C10B 122.1(5) . . ? C2B C1B H1B 118.9 . . ? C10B C1B H1B 118.9 . . ? C1B C2B C3B 122.2(5) . . ? C1B C2B H2B 118.9 . . ? C3B C2B H2B 118.9 . . ? O1B C3B N4B 122.0(5) . . ? O1B C3B C2B 122.4(5) . . ? N4B C3B C2B 115.6(4) . . ? N4B C5B C6B 112.1(4) . . ? N4B C5B C10B 110.8(4) . . ? C6B C5B C10B 112.3(4) . . ? N4B C5B H5B 107.1 . . ? C6B C5B H5B 107.1 . . ? C10B C5B H5B 107.1 . . ? C5B C6B C7B 109.4(4) . . ? C5B C6B H6C 109.8 . . ? C7B C6B H6C 109.8 . . ? C5B C6B H6D 109.8 . . ? C7B C6B H6D 109.8 . . ? H6C C6B H6D 108.2 . . ? C8B C7B C6B 113.8(4) . . ? C8B C7B H7C 108.8 . . ? C6B C7B H7C 108.8 . . ? C8B C7B H7D 108.8 . . ? C6B C7B H7D 108.8 . . ? H7C C7B H7D 107.7 . . ? C7B C8B C14B 111.9(4) . . ? C7B C8B C9B 110.3(4) . . ? C14B C8B C9B 108.8(4) . . ? C7B C8B H8B 108.5 . . ? C14B C8B H8B 108.5 . . ? C9B C8B H8B 108.5 . . ? C11B C9B C8B 112.5(4) . . ? C11B C9B C10B 114.1(4) . . ? C8B C9B C10B 110.5(4) . . ? C11B C9B H9B 106.4 . . ? C8B C9B H9B 106.4 . . ? C10B C9B H9B 106.4 . . ? C1B C10B C19B 107.3(5) . . ? C1B C10B C5B 104.9(4) . . ? C19B C10B C5B 112.0(4) . . ? C1B C10B C9B 112.9(4) . . ? C19B C10B C9B 112.9(4) . . ? C5B C10B C9B 106.6(4) . . ? C12B C11B C9B 112.8(5) . . ? C12B C11B H11C 109.0 . . ? C9B C11B H11C 109.0 . . ? C12B C11B H11D 109.0 . . ? C9B C11B H11D 109.0 . . ? H11C C11B H11D 107.8 . . ? C13B C12B C11B 110.4(4) . . ? C13B C12B H12C 109.6 . . ? C11B C12B H12C 109.6 . . ? C13B C12B H12D 109.6 . . ? C11B C12B H12D 109.6 . . ? H12C C12B H12D 108.1 . . ? C18B C13B C12B 110.6(5) . . ? C18B C13B C14B 113.0(4) . . ? C12B C13B C14B 107.9(4) . . ? C18B C13B C17B 109.4(4) . . ? C12B C13B C17B 116.2(4) . . ? C14B C13B C17B 99.4(4) . . ? C8B C14B C15B 118.8(4) . . ? C8B C14B C13B 114.3(4) . . ? C15B C14B C13B 103.4(4) . . ? C8B C14B H14B 106.5 . . ? C15B C14B H14B 106.5 . . ? C13B C14B H14B 106.5 . . ? C16B C15B C14B 103.8(4) . . ? C16B C15B H15C 111.0 . . ? C14B C15B H15C 111.0 . . ? C16B C15B H15D 111.0 . . ? C14B C15B H15D 111.0 . . ? H15C C15B H15D 109.0 . . ? C15B C16B C17B 106.7(4) . . ? C15B C16B H16C 110.4 . . ? C17B C16B H16C 110.4 . . ? C15B C16B H16D 110.4 . . ? C17B C16B H16D 110.4 . . ? H16C C16B H16D 108.6 . . ? C20B C17B C16B 112.3(4) . . ? C20B C17B C13B 114.9(4) . . ? C16B C17B C13B 104.0(4) . . ? C20B C17B H17B 108.5 . . ? C16B C17B H17B 108.5 . . ? C13B C17B H17B 108.5 . . ? C13B C18B H18D 109.5 . . ? C13B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C13B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C10B C19B H19D 109.5 . . ? C10B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C10B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? O2B C20B N21B 123.3(5) . . ? O2B C20B C17B 122.3(5) . . ? N21B C20B C17B 114.4(4) . . ? C27B C22B C23B 119.1(5) . . ? C27B C22B N21B 119.4(5) . . ? C23B C22B N21B 121.5(5) . . ? C24B C23B C22B 119.6(6) . . ? C24B C23B C28B 118.3(6) . . ? C22B C23B C28B 121.9(5) . . ? C25B C24B C23B 121.4(7) . . ? C25B C24B H24B 119.3 . . ? C23B C24B H24B 119.3 . . ? C26B C25B C24B 118.7(6) . . ? C26B C25B H25B 120.6 . . ? C24B C25B H25B 120.6 . . ? C25B C26B C27B 120.6(6) . . ? C25B C26B C29B 118.4(6) . . ? C27B C26B C29B 120.9(7) . . ? C22B C27B C26B 120.5(6) . . ? C22B C27B H27B 119.8 . . ? C26B C27B H27B 119.8 . . ? F12 C28B F2B 116.3(14) . . ? F12 C28B F32 113.5(11) . . ? F2B C28B F32 79.9(8) . . ? F12 C28B F3B 87.1(12) . . ? F2B C28B F3B 107.5(8) . . ? F2B C28B F1B 105.4(9) . . ? F32 C28B F1B 125.2(13) . . ? F3B C28B F1B 101.9(10) . . ? F12 C28B F22 106.5(9) . . ? F32 C28B F22 103.2(8) . . ? F3B C28B F22 129.8(8) . . ? F1B C28B F22 92.1(11) . . ? F12 C28B C23B 113.9(12) . . ? F2B C28B C23B 116.2(10) . . ? F32 C28B C23B 112.6(8) . . ? F3B C28B C23B 111.9(8) . . ? F1B C28B C23B 112.9(10) . . ? F22 C28B C23B 106.0(8) . . ? F5B C29B F6B 113.5(11) . . ? F5B C29B F42 122.2(11) . . ? F6B C29B F42 70.7(9) . . ? F6B C29B F52 128.5(11) . . ? F42 C29B F52 106.9(8) . . ? F5B C29B F62 82.8(10) . . ? F42 C29B F62 103.6(9) . . ? F52 C29B F62 103.9(9) . . ? F5B C29B F4B 105.7(8) . . ? F6B C29B F4B 102.1(9) . . ? F52 C29B F4B 84.3(9) . . ? F62 C29B F4B 131.7(9) . . ? F5B C29B C26B 112.7(10) . . ? F6B C29B C26B 113.8(7) . . ? F42 C29B C26B 117.0(8) . . ? F52 C29B C26B 112.2(10) . . ? F62 C29B C26B 112.0(7) . . ? F4B C29B C26B 108.0(8) . . ? C3B N4B C5B 121.2(4) . . ? C3B N4B H1N 113(3) . . ? C5B N4B H1N 125(3) . . ? C20B N21B C22B 122.1(5) . . ? C20B N21B H2N 119(3) . . ? C22B N21B H2N 118(3) . . ? H1W O1W H2W 106(3) . . ? 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 C10A C1A C2A C3A -0.2(11) . . . . ? C1A C2A C3A O1A 157.9(7) . . . . ? C1A C2A C3A N4A -18.9(10) . . . . ? N4A C5A C6A C7A 176.8(5) . . . . ? C10A C5A C6A C7A -59.1(8) . . . . ? C5A C6A C7A C8A 54.8(8) . . . . ? C6A C7A C8A C14A -174.7(5) . . . . ? C6A C7A C8A C9A -53.1(7) . . . . ? C14A C8A C9A C11A -54.1(5) . . . . ? C7A C8A C9A C11A -177.7(5) . . . . ? C14A C8A C9A C10A 177.2(4) . . . . ? C7A C8A C9A C10A 53.6(6) . . . . ? C2A C1A C10A C19A -82.7(7) . . . . ? C2A C1A C10A C5A 37.5(8) . . . . ? C2A C1A C10A C9A 154.0(6) . . . . ? N4A C5A C10A C1A -56.3(6) . . . . ? C6A C5A C10A C1A 178.6(5) . . . . ? N4A C5A C10A C19A 60.5(6) . . . . ? C6A C5A C10A C19A -64.6(6) . . . . ? N4A C5A C10A C9A -175.8(4) . . . . ? C6A C5A C10A C9A 59.1(6) . . . . ? C11A C9A C10A C1A 63.4(6) . . . . ? C8A C9A C10A C1A -169.3(4) . . . . ? C11A C9A C10A C19A -57.9(6) . . . . ? C8A C9A C10A C19A 69.4(6) . . . . ? C11A C9A C10A C5A 177.5(4) . . . . ? C8A C9A C10A C5A -55.1(5) . . . . ? C8A C9A C11A C12A 52.1(6) . . . . ? C10A C9A C11A C12A 179.5(4) . . . . ? C9A C11A C12A C13A -53.3(6) . . . . ? C11A C12A C13A C18A -69.7(5) . . . . ? C11A C12A C13A C14A 55.3(5) . . . . ? C11A C12A C13A C17A 164.8(4) . . . . ? C7A C8A C14A C15A -53.7(7) . . . . ? C9A C8A C14A C15A -176.9(5) . . . . ? C7A C8A C14A C13A -176.7(4) . . . . ? C9A C8A C14A C13A 60.0(5) . . . . ? C12A C13A C14A C8A -60.8(5) . . . . ? C18A C13A C14A C8A 62.7(5) . . . . ? C17A C13A C14A C8A 178.2(4) . . . . ? C12A C13A C14A C15A 168.2(5) . . . . ? C18A C13A C14A C15A -68.3(5) . . . . ? C17A C13A C14A C15A 47.1(5) . . . . ? C8A C14A C15A C16A -161.4(5) . . . . ? C13A C14A C15A C16A -34.2(6) . . . . ? C14A C15A C16A C17A 7.1(7) . . . . ? C15A C16A C17A C20A 147.4(5) . . . . ? C15A C16A C17A C13A 22.2(6) . . . . ? C12A C13A C17A C20A 79.3(5) . . . . ? C18A C13A C17A C20A -47.1(6) . . . . ? C14A C13A C17A C20A -165.8(4) . . . . ? C12A C13A C17A C16A -157.0(4) . . . . ? C18A C13A C17A C16A 76.7(5) . . . . ? C14A C13A C17A C16A -42.0(5) . . . . ? C16A C17A C20A O2A -20.0(7) . . . . ? C13A C17A C20A O2A 99.3(6) . . . . ? C16A C17A C20A N21A 159.6(4) . . . . ? C13A C17A C20A N21A -81.1(5) . . . . ? C27A C22A C23A C24A -1.6(8) . . . . ? N21A C22A C23A C24A -178.1(5) . . . . ? C27A C22A C23A C28A 179.5(5) . . . . ? N21A C22A C23A C28A 3.0(8) . . . . ? C22A C23A C24A C25A 2.1(9) . . . . ? C28A C23A C24A C25A -179.0(6) . . . . ? C23A C24A C25A C26A -0.6(10) . . . . ? C24A C25A C26A C27A -1.5(11) . . . . ? C24A C25A C26A C29A 177.1(7) . . . . ? N21A C22A C27A C26A 176.1(5) . . . . ? C23A C22A C27A C26A -0.5(8) . . . . ? C25A C26A C27A C22A 2.0(10) . . . . ? C29A C26A C27A C22A -176.6(6) . . . . ? C24A C23A C28A F2A -112.1(6) . . . . ? C22A C23A C28A F2A 66.8(7) . . . . ? C24A C23A C28A F3A 9.7(7) . . . . ? C22A C23A C28A F3A -171.3(5) . . . . ? C24A C23A C28A F1A 128.8(5) . . . . ? C22A C23A C28A F1A -52.3(6) . . . . ? C25A C26A C29A F51 -28.3(13) . . . . ? C27A C26A C29A F51 150.3(10) . . . . ? C25A C26A C29A F6A 49.1(12) . . . . ? C27A C26A C29A F6A -132.2(10) . . . . ? C25A C26A C29A F4A 172.5(10) . . . . ? C27A C26A C29A F4A -8.8(13) . . . . ? C25A C26A C29A F41 -155.5(9) . . . . ? C27A C26A C29A F41 23.2(12) . . . . ? C25A C26A C29A F5A -67.0(11) . . . . ? C27A C26A C29A F5A 111.6(9) . . . . ? C25A C26A C29A F61 90.0(10) . . . . ? C27A C26A C29A F61 -91.3(10) . . . . ? O1A C3A N4A C5A 177.8(5) . . . . ? C2A C3A N4A C5A -5.5(9) . . . . ? C6A C5A N4A C3A 171.2(6) . . . . ? C10A C5A N4A C3A 44.9(7) . . . . ? O2A C20A N21A C22A 9.7(8) . . . . ? C17A C20A N21A C22A -169.8(5) . . . . ? C27A C22A N21A C20A 28.3(8) . . . . ? C23A C22A N21A C20A -155.3(5) . . . . ? C10B C1B C2B C3B 1.1(11) . . . . ? C1B C2B C3B O1B 165.4(7) . . . . ? C1B C2B C3B N4B -13.9(10) . . . . ? N4B C5B C6B C7B 176.5(5) . . . . ? C10B C5B C6B C7B -57.9(7) . . . . ? C5B C6B C7B C8B 53.3(7) . . . . ? C6B C7B C8B C14B -174.9(5) . . . . ? C6B C7B C8B C9B -53.5(7) . . . . ? C7B C8B C9B C11B -174.2(5) . . . . ? C14B C8B C9B C11B -51.0(6) . . . . ? C7B C8B C9B C10B 57.0(5) . . . . ? C14B C8B C9B C10B -179.8(4) . . . . ? C2B C1B C10B C19B -87.6(7) . . . . ? C2B C1B C10B C5B 31.7(8) . . . . ? C2B C1B C10B C9B 147.3(6) . . . . ? N4B C5B C10B C1B -52.1(6) . . . . ? C6B C5B C10B C1B -178.4(5) . . . . ? N4B C5B C10B C19B 63.9(5) . . . . ? C6B C5B C10B C19B -62.4(6) . . . . ? N4B C5B C10B C9B -172.1(4) . . . . ? C6B C5B C10B C9B 61.6(5) . . . . ? C11B C9B C10B C1B 57.4(6) . . . . ? C8B C9B C10B C1B -174.7(4) . . . . ? C11B C9B C10B C19B -64.5(6) . . . . ? C8B C9B C10B C19B 63.4(5) . . . . ? C11B C9B C10B C5B 172.1(4) . . . . ? C8B C9B C10B C5B -60.0(5) . . . . ? C8B C9B C11B C12B 52.5(6) . . . . ? C10B C9B C11B C12B 179.3(4) . . . . ? C9B C11B C12B C13B -55.7(7) . . . . ? C11B C12B C13B C18B -66.7(5) . . . . ? C11B C12B C13B C14B 57.3(6) . . . . ? C11B C12B C13B C17B 167.8(4) . . . . ? C7B C8B C14B C15B -58.5(6) . . . . ? C9B C8B C14B C15B 179.2(4) . . . . ? C7B C8B C14B C13B 178.9(4) . . . . ? C9B C8B C14B C13B 56.7(5) . . . . ? C18B C13B C14B C8B 62.2(5) . . . . ? C12B C13B C14B C8B -60.4(5) . . . . ? C17B C13B C14B C8B 178.0(4) . . . . ? C18B C13B C14B C15B -68.5(5) . . . . ? C12B C13B C14B C15B 168.9(4) . . . . ? C17B C13B C14B C15B 47.4(4) . . . . ? C8B C14B C15B C16B -163.9(4) . . . . ? C13B C14B C15B C16B -36.1(5) . . . . ? C14B C15B C16B C17B 10.0(6) . . . . ? C15B C16B C17B C20B 144.2(4) . . . . ? C15B C16B C17B C13B 19.3(5) . . . . ? C18B C13B C17B C20B -45.2(6) . . . . ? C12B C13B C17B C20B 80.9(6) . . . . ? C14B C13B C17B C20B -163.7(4) . . . . ? C18B C13B C17B C16B 78.0(5) . . . . ? C12B C13B C17B C16B -155.9(4) . . . . ? C14B C13B C17B C16B -40.5(4) . . . . ? C16B C17B C20B O2B -32.0(7) . . . . ? C13B C17B C20B O2B 86.6(6) . . . . ? C16B C17B C20B N21B 149.2(5) . . . . ? C13B C17B C20B N21B -92.2(5) . . . . ? C27B C22B C23B C24B -0.7(10) . . . . ? N21B C22B C23B C24B 178.8(6) . . . . ? C27B C22B C23B C28B -175.9(6) . . . . ? N21B C22B C23B C28B 3.6(10) . . . . ? C22B C23B C24B C25B 0.8(13) . . . . ? C28B C23B C24B C25B 176.2(8) . . . . ? C23B C24B C25B C26B -0.3(14) . . . . ? C24B C25B C26B C27B -0.4(12) . . . . ? C24B C25B C26B C29B 177.6(8) . . . . ? C23B C22B C27B C26B 0.1(9) . . . . ? N21B C22B C27B C26B -179.5(5) . . . . ? C25B C26B C27B C22B 0.5(10) . . . . ? C29B C26B C27B C22B -177.4(6) . . . . ? C24B C23B C28B F12 121.3(10) . . . . ? C22B C23B C28B F12 -63.4(12) . . . . ? C24B C23B C28B F2B -99.4(10) . . . . ? C22B C23B C28B F2B 75.9(11) . . . . ? C24B C23B C28B F32 -9.8(12) . . . . ? C22B C23B C28B F32 165.5(9) . . . . ? C24B C23B C28B F3B 24.5(11) . . . . ? C22B C23B C28B F3B -160.2(9) . . . . ? C24B C23B C28B F1B 138.7(10) . . . . ? C22B C23B C28B F1B -46.0(11) . . . . ? C24B C23B C28B F22 -121.9(9) . . . . ? C22B C23B C28B F22 53.3(10) . . . . ? C25B C26B C29B F5B -76.4(12) . . . . ? C27B C26B C29B F5B 101.5(10) . . . . ? C25B C26B C29B F6B 152.6(10) . . . . ? C27B C26B C29B F6B -29.5(12) . . . . ? C25B C26B C29B F42 73.0(12) . . . . ? C27B C26B C29B F42 -109.1(10) . . . . ? C25B C26B C29B F52 -51.1(11) . . . . ? C27B C26B C29B F52 126.8(9) . . . . ? C25B C26B C29B F62 -167.6(9) . . . . ? C27B C26B C29B F62 10.3(11) . . . . ? C25B C26B C29B F4B 40.0(11) . . . . ? C27B C26B C29B F4B -142.1(8) . . . . ? O1B C3B N4B C5B 168.8(5) . . . . ? C2B C3B N4B C5B -11.8(9) . . . . ? C6B C5B N4B C3B 173.1(5) . . . . ? C10B C5B N4B C3B 46.7(7) . . . . ? O2B C20B N21B C22B 3.6(8) . . . . ? C17B C20B N21B C22B -177.6(5) . . . . ? C27B C22B N21B C20B 48.7(7) . . . . ? C23B C22B N21B C20B -130.8(6) . . . . ? 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 N4A H3N O1B 0.82(2) 2.08(2) 2.897(6) 170(5) . N21A H4N F1A 0.83(2) 2.28(7) 2.807(5) 122(7) . N4B H1N O1A 0.83(5) 2.10(5) 2.906(6) 162(4) . N21B H2N O1W 0.82(4) 2.03(5) 2.839(6) 172(4) 4_456 O1W H2W O1B 0.89(2) 1.92(2) 2.801(6) 174(8) . O1W H1W O1A 0.89(2) 1.91(3) 2.753(5) 159(5) 1_655 C16A H16A O2A 0.97 2.45 2.856(7) 104.7 . C16B H16D O2B 0.97 2.44 2.869(7) 106.2 . C18B H18E F2A 0.96 2.51 3.319(6) 141.4 2_465 C19A H19A N4A 0.96 2.59 2.961(8) 103.1 . C19A H19C F32 0.96 2.54 3.415(12) 151.5 2_564 C19B H19D O2A 0.96 2.47 3.381(7) 159.3 2_565 C24A H24A F3A 0.93 2.34 2.679(7) 101.2 . C24B H24B F32 0.93 2.33 2.677(16) 101.4 . C27A H27A O2A 0.93 2.34 2.851(6) 114.0 . C27B H27B F62 0.93 2.40 2.721(12) 100.3 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.798 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.058 # Attachment '7710_web_deposit_cif_file_2_B.Sridhar_1319087400.ajf.cif' data_aj_(salt) _database_code_depnum_ccdc_archive 'CCDC 849483' #TrackingRef '7710_web_deposit_cif_file_2_B.Sridhar_1319087400.ajf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 'Dutasteride chloride hydrate ethanol solvate' ; _chemical_melting_point ? _chemical_formula_moiety 'C27 H31 F6 N2 O2 +, Cl -, H2 O, C2 H6 O' _chemical_formula_sum 'C29 H39 Cl F6 N2 O4' _chemical_formula_weight 629.07 _chemical_absolute_configuration rmad 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' Cl Cl 0.1484 0.1585 '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' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.9357(7) _cell_length_b 9.1050(8) _cell_length_c 11.1952(9) _cell_angle_alpha 73.7460(10) _cell_angle_beta 88.6870(10) _cell_angle_gamma 86.1930(10) _cell_volume 774.85(11) _cell_formula_units_Z 1 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3522 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 24.24 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 330 _exptl_absorpt_coefficient_mu 0.195 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7533 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5376 _reflns_number_gt 5048 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0461P)^2^+0.1410P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(6) _refine_ls_number_reflns 5376 _refine_ls_number_parameters 461 _refine_ls_number_restraints 145 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.111 _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 1.1452(3) 0.7437(3) 0.6993(3) 0.0478(7) Uani 1 1 d . . . H1 H 1.1953 0.8185 0.6371 0.057 Uiso 1 1 calc R . . C2 C 1.2025(4) 0.7099(3) 0.8145(3) 0.0532(7) Uani 1 1 d . . . H2 H 1.2943 0.7587 0.8320 0.064 Uiso 1 1 calc R . . C3 C 1.1223(4) 0.5967(3) 0.9138(3) 0.0535(7) Uani 1 1 d . . . C5 C 0.8806(4) 0.6343(4) 0.7802(3) 0.0505(7) Uani 1 1 d . . . H5 H 0.8362 0.7345 0.7874 0.061 Uiso 1 1 calc R . . C6 C 0.7315(4) 0.5461(4) 0.7654(3) 0.0633(9) Uani 1 1 d . . . H6A H 0.6609 0.5283 0.8394 0.076 Uiso 1 1 calc R . . H6B H 0.7706 0.4475 0.7543 0.076 Uiso 1 1 calc R . . C7 C 0.6300(4) 0.6393(5) 0.6521(3) 0.0619(9) Uani 1 1 d . . . H7A H 0.5828 0.7334 0.6675 0.074 Uiso 1 1 calc R . . H7B H 0.5370 0.5813 0.6397 0.074 Uiso 1 1 calc R . . C8 C 0.7387(3) 0.6787(3) 0.5339(2) 0.0440(6) Uani 1 1 d . . . H8 H 0.7767 0.5829 0.5151 0.053 Uiso 1 1 calc R . . C9 C 0.8958(3) 0.7602(3) 0.5530(2) 0.0409(6) Uani 1 1 d . . . H9 H 0.8544 0.8545 0.5727 0.049 Uiso 1 1 calc R . . C10 C 0.9998(3) 0.6631(3) 0.6669(3) 0.0420(6) Uani 1 1 d . . . C11 C 1.0004(4) 0.8090(4) 0.4335(3) 0.0520(7) Uani 1 1 d . . . H11A H 1.0523 0.7182 0.4152 0.062 Uiso 1 1 calc R . . H11B H 1.0902 0.8698 0.4468 0.062 Uiso 1 1 calc R . . C12 C 0.8956(4) 0.9026(4) 0.3205(3) 0.0527(7) Uani 1 1 d . . . H12A H 0.8554 1.0000 0.3334 0.063 Uiso 1 1 calc R . . H12B H 0.9663 0.9234 0.2466 0.063 Uiso 1 1 calc R . . C13 C 0.7450(3) 0.8152(3) 0.3013(2) 0.0411(6) Uani 1 1 d . . . C14 C 0.6416(3) 0.7796(3) 0.4230(2) 0.0459(6) Uani 1 1 d . . . H14 H 0.6144 0.8778 0.4410 0.055 Uiso 1 1 calc R . . C15 C 0.4759(4) 0.7274(5) 0.3866(3) 0.0665(9) Uani 1 1 d . . . H15A H 0.3850 0.7417 0.4425 0.080 Uiso 1 1 calc R . . H15B H 0.4872 0.6203 0.3875 0.080 Uiso 1 1 calc R . . C16 C 0.4433(4) 0.8316(4) 0.2537(3) 0.0580(8) Uani 1 1 d . . . H16A H 0.3508 0.9068 0.2537 0.070 Uiso 1 1 calc R . . H16B H 0.4148 0.7712 0.1990 0.070 Uiso 1 1 calc R . . C17 C 0.6086(3) 0.9120(3) 0.2098(3) 0.0467(6) Uani 1 1 d . . . H17 H 0.5967 1.0146 0.2222 0.056 Uiso 1 1 calc R . . C18 C 0.8033(4) 0.6723(4) 0.2628(3) 0.0597(8) Uani 1 1 d . . . H18A H 0.8633 0.7015 0.1851 0.090 Uiso 1 1 calc R . . H18B H 0.7069 0.6181 0.2535 0.090 Uiso 1 1 calc R . . H18C H 0.8766 0.6071 0.3254 0.090 Uiso 1 1 calc R . . C19 C 1.0791(4) 0.5138(3) 0.6451(3) 0.0555(7) Uani 1 1 d . . . H19A H 1.1674 0.5375 0.5840 0.083 Uiso 1 1 calc R . . H19B H 0.9941 0.4620 0.6160 0.083 Uiso 1 1 calc R . . H19C H 1.1252 0.4488 0.7217 0.083 Uiso 1 1 calc R . . C20 C 0.6496(3) 0.9291(3) 0.0742(3) 0.0439(6) Uani 1 1 d . . . C22 C 0.7865(3) 1.0812(3) -0.1093(3) 0.0441(6) Uani 1 1 d . . . C23 C 0.9526(4) 1.0857(3) -0.1510(3) 0.0480(6) Uani 1 1 d . . . C24 C 0.9860(4) 1.1228(4) -0.2776(3) 0.0567(8) Uani 1 1 d . . . H24 H 1.0973 1.1266 -0.3056 0.068 Uiso 1 1 calc R . . C25 C 0.8570(4) 1.1542(4) -0.3622(3) 0.0583(8) Uani 1 1 d . . . H25 H 0.8806 1.1794 -0.4470 0.070 Uiso 1 1 calc R . . C26 C 0.6935(4) 1.1481(3) -0.3209(3) 0.0541(7) Uani 1 1 d . A . C27 C 0.6584(4) 1.1126(3) -0.1943(3) 0.0521(7) Uani 1 1 d . . . H27 H 0.5468 1.1100 -0.1670 0.062 Uiso 1 1 calc R . . C28 C 1.0963(4) 1.0488(4) -0.0601(3) 0.0643(8) Uani 1 1 d . . . C29 C 0.5511(6) 1.1840(5) -0.4101(4) 0.0801(10) Uani 1 1 d U . . F1 F 1.0960(3) 0.9057(3) 0.0134(2) 0.0917(7) Uani 1 1 d . . . F2 F 1.0917(3) 1.1391(3) 0.0136(3) 0.1000(8) Uani 1 1 d . . . F3 F 1.2452(3) 1.0584(4) -0.1173(2) 0.1053(9) Uani 1 1 d . . . F4 F 0.4364(11) 1.0709(9) -0.3770(7) 0.103(2) Uani 0.537(11) 1 d PDU A 1 F5 F 0.6001(7) 1.1781(11) -0.5224(5) 0.0948(18) Uani 0.537(11) 1 d PDU A 1 F6 F 0.4704(13) 1.3073(8) -0.4165(9) 0.111(2) Uani 0.537(11) 1 d PDU A 1 F41 F 0.4811(15) 1.0641(8) -0.4217(10) 0.102(2) Uani 0.463(11) 1 d PDU A 2 F51 F 0.5839(9) 1.2738(14) -0.5193(7) 0.118(3) Uani 0.463(11) 1 d PDU A 2 F61 F 0.4171(10) 1.2658(11) -0.3698(8) 0.095(2) Uani 0.463(11) 1 d PDU A 2 N4 N 0.9740(4) 0.5578(3) 0.8943(2) 0.0576(7) Uani 1 1 d . . . H1N H 0.926(5) 0.500(4) 0.945(4) 0.060(11) Uiso 1 1 d . . . N21 N 0.7462(3) 1.0451(3) 0.0195(2) 0.0465(6) Uani 1 1 d . . . H2N H 0.764(3) 1.108(3) 0.053(3) 0.056(8) Uiso 1 1 d . . . O1 O 1.1928(3) 0.5343(3) 1.0188(2) 0.0729(7) Uani 1 1 d . . . H1O H 1.302(6) 0.557(5) 1.023(4) 0.085(12) Uiso 1 1 d . . . O2 O 0.6055(3) 0.8425(2) 0.01634(19) 0.0603(6) Uani 1 1 d . . . Cl1 Cl 0.77023(9) 0.33651(8) 0.12046(7) 0.0571(2) Uani 1 1 d . . . O1W O 0.4844(3) 0.5763(3) 0.0440(3) 0.0885(9) Uani 1 1 d D . . H1W H 0.527(5) 0.663(2) 0.028(5) 0.110(16) Uiso 1 1 d D . . H2W H 0.563(4) 0.510(3) 0.053(4) 0.106(12) Uiso 1 1 d D . . C30 C 1.1602(9) 0.3399(10) 0.3313(6) 0.0912(19) Uani 0.727(10) 1 d PDU B 1 H30A H 1.2161 0.3528 0.4035 0.109 Uiso 0.727(10) 1 calc PR B 1 H30B H 1.1531 0.4391 0.2698 0.109 Uiso 0.727(10) 1 calc PR B 1 C31 C 1.2700(10) 0.2366(9) 0.2804(7) 0.101(2) Uani 0.727(10) 1 d PDU B 1 H31A H 1.3781 0.2789 0.2599 0.151 Uiso 0.727(10) 1 calc PR B 1 H31B H 1.2199 0.2244 0.2068 0.151 Uiso 0.727(10) 1 calc PR B 1 H31C H 1.2843 0.1386 0.3411 0.151 Uiso 0.727(10) 1 calc PR B 1 O3 O 0.9943(10) 0.3007(8) 0.3670(8) 0.096(2) Uani 0.727(10) 1 d PDU B 1 C301 C 1.179(3) 0.233(2) 0.322(2) 0.101(3) Uani 0.273(10) 1 d PDU B 2 H30C H 1.1869 0.2152 0.2410 0.121 Uiso 0.273(10) 1 calc PR B 2 H30D H 1.2456 0.1525 0.3809 0.121 Uiso 0.273(10) 1 calc PR B 2 C311 C 1.238(3) 0.394(2) 0.3181(19) 0.098(3) Uani 0.273(10) 1 d PDU B 2 H31D H 1.3531 0.4010 0.2897 0.147 Uiso 0.273(10) 1 calc PR B 2 H31E H 1.2301 0.4080 0.3998 0.147 Uiso 0.273(10) 1 calc PR B 2 H31F H 1.1675 0.4713 0.2621 0.147 Uiso 0.273(10) 1 calc PR B 2 O31 O 1.013(3) 0.240(2) 0.361(2) 0.096(4) Uani 0.273(10) 1 d PDU B 2 H3O H 0.930(7) 0.317(6) 0.299(5) 0.114(18) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0445(15) 0.0463(15) 0.0478(16) -0.0041(12) -0.0017(12) -0.0075(12) C2 0.0507(16) 0.0587(18) 0.0486(17) -0.0089(14) -0.0057(13) -0.0159(14) C3 0.0539(17) 0.0598(18) 0.0424(16) -0.0055(14) -0.0078(13) -0.0087(14) C5 0.0468(16) 0.0638(18) 0.0364(14) -0.0055(13) -0.0016(12) -0.0075(13) C6 0.0497(18) 0.088(2) 0.0409(16) 0.0056(15) 0.0013(14) -0.0258(16) C7 0.0414(16) 0.095(2) 0.0397(16) 0.0009(16) 0.0016(13) -0.0203(16) C8 0.0404(14) 0.0499(15) 0.0379(15) -0.0043(12) 0.0000(12) -0.0100(12) C9 0.0420(14) 0.0422(14) 0.0372(13) -0.0082(11) 0.0021(11) -0.0062(11) C10 0.0400(14) 0.0420(15) 0.0417(14) -0.0069(12) -0.0011(11) -0.0071(11) C11 0.0410(15) 0.0649(18) 0.0430(15) -0.0006(13) -0.0019(12) -0.0156(13) C12 0.0462(16) 0.0647(19) 0.0407(16) -0.0011(13) 0.0003(12) -0.0159(14) C13 0.0401(14) 0.0451(15) 0.0346(14) -0.0049(11) -0.0001(11) -0.0058(11) C14 0.0398(15) 0.0551(17) 0.0390(15) -0.0070(12) 0.0012(11) -0.0023(12) C15 0.0371(15) 0.102(3) 0.0508(18) -0.0028(17) -0.0027(13) -0.0187(16) C16 0.0389(15) 0.082(2) 0.0467(17) -0.0071(15) -0.0023(13) -0.0047(14) C17 0.0465(16) 0.0480(15) 0.0419(15) -0.0068(12) -0.0036(12) -0.0013(12) C18 0.0629(19) 0.065(2) 0.0486(17) -0.0123(15) -0.0075(14) 0.0064(15) C19 0.0587(18) 0.0504(17) 0.0528(18) -0.0077(14) -0.0057(14) 0.0023(14) C20 0.0400(15) 0.0481(16) 0.0394(14) -0.0049(13) -0.0062(11) -0.0021(12) C22 0.0493(16) 0.0375(14) 0.0443(15) -0.0080(12) 0.0002(12) -0.0088(11) C23 0.0497(16) 0.0432(14) 0.0509(16) -0.0121(12) 0.0067(13) -0.0082(12) C24 0.0512(17) 0.0577(18) 0.0592(19) -0.0127(15) 0.0150(15) -0.0096(14) C25 0.079(2) 0.0522(17) 0.0402(16) -0.0074(13) 0.0076(16) -0.0074(16) C26 0.0627(19) 0.0494(17) 0.0468(16) -0.0071(13) -0.0005(14) -0.0064(14) C27 0.0490(16) 0.0583(17) 0.0470(16) -0.0104(14) 0.0025(13) -0.0103(13) C28 0.0489(18) 0.081(2) 0.064(2) -0.0226(19) 0.0028(15) -0.0037(16) C29 0.088(2) 0.097(3) 0.052(2) -0.0160(19) -0.0166(18) 0.002(2) F1 0.0800(14) 0.1061(18) 0.0734(14) -0.0035(13) -0.0142(11) 0.0157(13) F2 0.0714(14) 0.138(2) 0.1136(19) -0.0719(17) -0.0223(13) -0.0057(13) F3 0.0441(11) 0.172(3) 0.0943(17) -0.0295(17) 0.0066(11) -0.0078(13) F4 0.086(4) 0.155(4) 0.064(4) -0.017(3) -0.012(3) -0.036(3) F5 0.098(3) 0.141(5) 0.048(2) -0.029(3) -0.016(2) 0.002(3) F6 0.125(5) 0.114(4) 0.090(4) -0.027(3) -0.043(4) 0.040(3) F41 0.112(5) 0.120(4) 0.082(5) -0.039(3) -0.030(4) -0.012(3) F51 0.105(4) 0.148(5) 0.063(3) 0.034(4) -0.014(3) 0.005(4) F61 0.072(4) 0.137(5) 0.064(4) -0.017(3) -0.013(3) 0.027(3) N4 0.0541(16) 0.0727(18) 0.0384(14) 0.0007(13) -0.0015(12) -0.0203(14) N21 0.0495(14) 0.0512(14) 0.0414(13) -0.0147(12) 0.0005(10) -0.0135(11) O1 0.0671(16) 0.0902(18) 0.0500(14) 0.0047(12) -0.0189(12) -0.0226(13) O2 0.0824(15) 0.0557(12) 0.0425(11) -0.0078(10) -0.0022(10) -0.0262(11) Cl1 0.0650(5) 0.0518(4) 0.0530(4) -0.0114(3) 0.0012(3) -0.0072(3) O1W 0.0627(16) 0.0584(16) 0.141(3) -0.0181(17) -0.0328(16) -0.0083(13) C30 0.090(4) 0.114(5) 0.065(3) -0.016(3) 0.002(3) -0.007(4) C31 0.102(5) 0.119(5) 0.079(4) -0.026(3) 0.004(3) 0.002(4) O3 0.095(3) 0.122(5) 0.055(2) -0.002(4) 0.002(2) -0.002(4) C301 0.103(5) 0.122(6) 0.074(5) -0.020(5) -0.001(5) -0.006(6) C311 0.098(7) 0.126(7) 0.067(6) -0.021(6) -0.006(6) -0.006(6) O31 0.099(6) 0.115(7) 0.067(5) -0.008(6) -0.006(5) -0.019(6) _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 C2 1.324(4) . ? C1 C10 1.510(4) . ? C1 H1 0.9300 . ? C2 C3 1.455(4) . ? C2 H2 0.9300 . ? C3 O1 1.277(3) . ? C3 N4 1.292(4) . ? C5 N4 1.465(4) . ? C5 C6 1.510(4) . ? C5 C10 1.537(4) . ? C5 H5 0.9800 . ? C6 C7 1.527(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.531(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C14 1.514(4) . ? C8 C9 1.541(3) . ? C8 H8 0.9800 . ? C9 C11 1.530(4) . ? C9 C10 1.552(4) . ? C9 H9 0.9800 . ? C10 C19 1.539(4) . ? C11 C12 1.539(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.530(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.523(4) . ? C13 C14 1.539(4) . ? C13 C17 1.555(4) . ? C14 C15 1.529(4) . ? C14 H14 0.9800 . ? C15 C16 1.541(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.547(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C20 1.512(4) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 O2 1.224(3) . ? C20 N21 1.342(4) . ? C22 C27 1.369(4) . ? C22 C23 1.387(4) . ? C22 N21 1.420(4) . ? C23 C24 1.385(4) . ? C23 C28 1.504(5) . ? C24 C25 1.371(5) . ? C24 H24 0.9300 . ? C25 C26 1.367(4) . ? C25 H25 0.9300 . ? C26 C27 1.388(4) . ? C26 C29 1.484(5) . ? C27 H27 0.9300 . ? C28 F2 1.316(4) . ? C28 F3 1.327(4) . ? C28 F1 1.332(4) . ? C29 F6 1.240(7) . ? C29 F41 1.297(9) . ? C29 F51 1.298(6) . ? C29 F5 1.321(6) . ? C29 F4 1.386(7) . ? C29 F61 1.397(7) . ? N4 H1N 0.77(4) . ? N21 H2N 0.79(3) . ? O1 H1O 0.91(4) . ? O1W H1W 0.854(19) . ? O1W H2W 0.832(18) . ? C30 O3 1.407(9) . ? C30 C31 1.462(10) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? O3 H3O 0.90(6) . ? C301 O31 1.379(18) . ? C301 C311 1.553(19) . ? C301 H30C 0.9700 . ? C301 H30D 0.9700 . ? C311 H31D 0.9600 . ? C311 H31E 0.9600 . ? C311 H31F 0.9600 . ? O31 H3O 1.05(6) . ? 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 C2 C1 C10 121.3(3) . . ? C2 C1 H1 119.4 . . ? C10 C1 H1 119.4 . . ? C1 C2 C3 120.2(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? O1 C3 N4 119.0(3) . . ? O1 C3 C2 122.7(3) . . ? N4 C3 C2 118.4(3) . . ? N4 C5 C6 111.4(2) . . ? N4 C5 C10 110.4(2) . . ? C6 C5 C10 112.5(2) . . ? N4 C5 H5 107.4 . . ? C6 C5 H5 107.4 . . ? C10 C5 H5 107.4 . . ? C5 C6 C7 108.7(3) . . ? C5 C6 H6A 109.9 . . ? C7 C6 H6A 109.9 . . ? C5 C6 H6B 109.9 . . ? C7 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C6 C7 C8 112.0(3) . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C14 C8 C7 112.2(2) . . ? C14 C8 C9 108.7(2) . . ? C7 C8 C9 111.0(2) . . ? C14 C8 H8 108.3 . . ? C7 C8 H8 108.3 . . ? C9 C8 H8 108.3 . . ? C11 C9 C8 111.7(2) . . ? C11 C9 C10 113.6(2) . . ? C8 C9 C10 111.2(2) . . ? C11 C9 H9 106.6 . . ? C8 C9 H9 106.6 . . ? C10 C9 H9 106.6 . . ? C1 C10 C5 105.8(2) . . ? C1 C10 C19 105.5(2) . . ? C5 C10 C19 112.7(2) . . ? C1 C10 C9 113.9(2) . . ? C5 C10 C9 107.0(2) . . ? C19 C10 C9 111.8(2) . . ? C9 C11 C12 113.2(2) . . ? C9 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C9 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 110.7(2) . . ? C13 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C18 C13 C12 111.0(2) . . ? C18 C13 C14 113.1(2) . . ? C12 C13 C14 107.3(2) . . ? C18 C13 C17 110.2(2) . . ? C12 C13 C17 115.1(2) . . ? C14 C13 C17 99.7(2) . . ? C8 C14 C15 119.3(2) . . ? C8 C14 C13 113.5(2) . . ? C15 C14 C13 103.6(2) . . ? C8 C14 H14 106.6 . . ? C15 C14 H14 106.6 . . ? C13 C14 H14 106.6 . . ? C14 C15 C16 103.7(2) . . ? C14 C15 H15A 111.0 . . ? C16 C15 H15A 111.0 . . ? C14 C15 H15B 111.0 . . ? C16 C15 H15B 111.0 . . ? H15A C15 H15B 109.0 . . ? C15 C16 C17 106.6(2) . . ? C15 C16 H16A 110.4 . . ? C17 C16 H16A 110.4 . . ? C15 C16 H16B 110.4 . . ? C17 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? C20 C17 C16 113.6(2) . . ? C20 C17 C13 114.1(2) . . ? C16 C17 C13 104.4(2) . . ? C20 C17 H17 108.2 . . ? C16 C17 H17 108.2 . . ? C13 C17 H17 108.2 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 N21 120.5(3) . . ? O2 C20 C17 124.2(3) . . ? N21 C20 C17 115.3(2) . . ? C27 C22 C23 119.2(3) . . ? C27 C22 N21 119.2(3) . . ? C23 C22 N21 121.6(2) . . ? C24 C23 C22 119.6(3) . . ? C24 C23 C28 119.8(3) . . ? C22 C23 C28 120.6(3) . . ? C25 C24 C23 120.8(3) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C26 C25 C24 119.5(3) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C27 120.2(3) . . ? C25 C26 C29 120.8(3) . . ? C27 C26 C29 119.0(3) . . ? C22 C27 C26 120.6(3) . . ? C22 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? F2 C28 F3 108.0(3) . . ? F2 C28 F1 106.6(3) . . ? F3 C28 F1 105.4(3) . . ? F2 C28 C23 112.7(3) . . ? F3 C28 C23 111.8(3) . . ? F1 C28 C23 111.9(3) . . ? F6 C29 F41 122.8(7) . . ? F6 C29 F51 74.1(6) . . ? F41 C29 F51 109.7(6) . . ? F6 C29 F5 110.2(5) . . ? F41 C29 F5 77.2(6) . . ? F6 C29 F4 106.6(6) . . ? F51 C29 F4 129.1(6) . . ? F5 C29 F4 102.7(5) . . ? F41 C29 F61 102.7(6) . . ? F51 C29 F61 102.2(6) . . ? F5 C29 F61 131.9(5) . . ? F4 C29 F61 80.4(6) . . ? F6 C29 C26 114.4(5) . . ? F41 C29 C26 114.0(6) . . ? F51 C29 C26 115.3(5) . . ? F5 C29 C26 112.0(4) . . ? F4 C29 C26 110.3(4) . . ? F61 C29 C26 111.5(4) . . ? C3 N4 C5 121.6(3) . . ? C3 N4 H1N 122(3) . . ? C5 N4 H1N 116(3) . . ? C20 N21 C22 121.7(2) . . ? C20 N21 H2N 120(2) . . ? C22 N21 H2N 116(2) . . ? C3 O1 H1O 115(3) . . ? H1W O1W H2W 108(3) . . ? O3 C30 C31 119.2(9) . . ? O3 C30 H30A 107.5 . . ? C31 C30 H30A 107.5 . . ? O3 C30 H30B 107.5 . . ? C31 C30 H30B 107.5 . . ? H30A C30 H30B 107.0 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 O3 H3O 110(3) . . ? O31 C301 C311 103(2) . . ? O31 C301 H30C 111.1 . . ? C311 C301 H30C 111.1 . . ? O31 C301 H30D 111.1 . . ? C311 C301 H30D 111.1 . . ? H30C C301 H30D 109.1 . . ? C301 C311 H31D 109.5 . . ? C301 C311 H31E 109.5 . . ? H31D C311 H31E 109.5 . . ? C301 C311 H31F 109.5 . . ? H31D C311 H31F 109.5 . . ? H31E C311 H31F 109.5 . . ? C301 O31 H3O 116(4) . . ? 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 C10 C1 C2 C3 -1.9(5) . . . . ? C1 C2 C3 O1 163.7(3) . . . . ? C1 C2 C3 N4 -16.1(5) . . . . ? N4 C5 C6 C7 174.5(3) . . . . ? C10 C5 C6 C7 -60.9(4) . . . . ? C5 C6 C7 C8 56.2(4) . . . . ? C6 C7 C8 C14 -176.3(3) . . . . ? C6 C7 C8 C9 -54.5(4) . . . . ? C14 C8 C9 C11 -52.7(3) . . . . ? C7 C8 C9 C11 -176.6(3) . . . . ? C14 C8 C9 C10 179.2(2) . . . . ? C7 C8 C9 C10 55.4(3) . . . . ? C2 C1 C10 C5 35.3(4) . . . . ? C2 C1 C10 C19 -84.4(3) . . . . ? C2 C1 C10 C9 152.6(3) . . . . ? N4 C5 C10 C1 -51.8(3) . . . . ? C6 C5 C10 C1 -177.0(2) . . . . ? N4 C5 C10 C19 63.0(3) . . . . ? C6 C5 C10 C19 -62.1(3) . . . . ? N4 C5 C10 C9 -173.7(2) . . . . ? C6 C5 C10 C9 61.2(3) . . . . ? C11 C9 C10 C1 59.2(3) . . . . ? C8 C9 C10 C1 -173.8(2) . . . . ? C11 C9 C10 C5 175.8(2) . . . . ? C8 C9 C10 C5 -57.2(3) . . . . ? C11 C9 C10 C19 -60.3(3) . . . . ? C8 C9 C10 C19 66.7(3) . . . . ? C8 C9 C11 C12 52.2(3) . . . . ? C10 C9 C11 C12 178.9(2) . . . . ? C9 C11 C12 C13 -54.8(3) . . . . ? C11 C12 C13 C18 -67.1(3) . . . . ? C11 C12 C13 C14 56.9(3) . . . . ? C11 C12 C13 C17 166.8(2) . . . . ? C7 C8 C14 C15 -54.8(4) . . . . ? C9 C8 C14 C15 -177.9(3) . . . . ? C7 C8 C14 C13 -177.4(3) . . . . ? C9 C8 C14 C13 59.5(3) . . . . ? C18 C13 C14 C8 60.9(3) . . . . ? C12 C13 C14 C8 -61.9(3) . . . . ? C17 C13 C14 C8 177.9(2) . . . . ? C18 C13 C14 C15 -69.9(3) . . . . ? C12 C13 C14 C15 167.3(3) . . . . ? C17 C13 C14 C15 47.1(3) . . . . ? C8 C14 C15 C16 -164.5(3) . . . . ? C13 C14 C15 C16 -37.2(3) . . . . ? C14 C15 C16 C17 12.3(4) . . . . ? C15 C16 C17 C20 141.6(3) . . . . ? C15 C16 C17 C13 16.8(3) . . . . ? C18 C13 C17 C20 -44.0(3) . . . . ? C12 C13 C17 C20 82.5(3) . . . . ? C14 C13 C17 C20 -163.1(2) . . . . ? C18 C13 C17 C16 80.5(3) . . . . ? C12 C13 C17 C16 -153.0(3) . . . . ? C14 C13 C17 C16 -38.6(3) . . . . ? C16 C17 C20 O2 -27.9(4) . . . . ? C13 C17 C20 O2 91.5(3) . . . . ? C16 C17 C20 N21 154.7(3) . . . . ? C13 C17 C20 N21 -85.9(3) . . . . ? C27 C22 C23 C24 0.5(4) . . . . ? N21 C22 C23 C24 -179.4(3) . . . . ? C27 C22 C23 C28 -178.8(3) . . . . ? N21 C22 C23 C28 1.4(4) . . . . ? C22 C23 C24 C25 -0.4(4) . . . . ? C28 C23 C24 C25 178.8(3) . . . . ? C23 C24 C25 C26 -0.2(5) . . . . ? C24 C25 C26 C27 0.9(5) . . . . ? C24 C25 C26 C29 179.0(3) . . . . ? C23 C22 C27 C26 0.2(4) . . . . ? N21 C22 C27 C26 -180.0(3) . . . . ? C25 C26 C27 C22 -0.8(5) . . . . ? C29 C26 C27 C22 -179.0(3) . . . . ? C24 C23 C28 F2 122.3(3) . . . . ? C22 C23 C28 F2 -58.5(4) . . . . ? C24 C23 C28 F3 0.4(4) . . . . ? C22 C23 C28 F3 179.7(3) . . . . ? C24 C23 C28 F1 -117.6(3) . . . . ? C22 C23 C28 F1 61.7(4) . . . . ? C25 C26 C29 F6 -108.7(7) . . . . ? C27 C26 C29 F6 69.4(8) . . . . ? C25 C26 C29 F41 102.8(7) . . . . ? C27 C26 C29 F41 -79.1(7) . . . . ? C25 C26 C29 F51 -25.5(9) . . . . ? C27 C26 C29 F51 152.6(8) . . . . ? C25 C26 C29 F5 17.5(7) . . . . ? C27 C26 C29 F5 -164.4(5) . . . . ? C25 C26 C29 F4 131.2(6) . . . . ? C27 C26 C29 F4 -50.7(7) . . . . ? C25 C26 C29 F61 -141.5(6) . . . . ? C27 C26 C29 F61 36.7(7) . . . . ? O1 C3 N4 C5 174.8(3) . . . . ? C2 C3 N4 C5 -5.4(5) . . . . ? C6 C5 N4 C3 166.8(3) . . . . ? C10 C5 N4 C3 41.0(4) . . . . ? O2 C20 N21 C22 6.4(4) . . . . ? C17 C20 N21 C22 -176.1(2) . . . . ? C27 C22 N21 C20 56.4(4) . . . . ? C23 C22 N21 C20 -123.7(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 N4 H1N Cl1 0.77(4) 2.47(4) 3.236(3) 174(3) 1_556 N21 H2N Cl1 0.79(3) 2.41(3) 3.179(3) 166(3) 1_565 O1 H1O O1W 0.91(4) 1.50(5) 2.406(3) 173(4) 1_656 O1W H1W O2 0.85(2) 1.75(2) 2.602(3) 172(5) . O1W H2W Cl1 0.83(2) 2.19(2) 3.005(3) 167(4) . O3 H3O Cl1 0.90(5) 2.35(5) 3.245(8) 175(5) . C16 H16B O2 0.97 2.48 2.905(4) 107 . C24 H24 F3 0.93 2.34 2.687(4) 101 . C25 H25 O3 0.93 2.26 3.152(8) 159 1_564 C27 H27 F3 0.93 2.49 3.404(4) 167 1_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.251 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.040