# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name _publ_author_address 'Brazeau, Allison' ;Department of Chemistry The University of Western Ontario Chemistry Building, 1151 Richmond St. London, Ontario, Canada N6A 5B7 ; 'Caputo, Christine' ;Department of Chemistry The University of Western Ontario Chemistry Building, 1151 Richmond St. London, Ontario, Canada N6A 5B7 ; 'Jones, Nathan' ;Department of Chemistry The University of Western Ontario Chemistry Building, 1151 Richmond St. London, Ontario, Canada N6A 5B7 ; 'Ragogna, Paul' ;Department of Chemistry The University of Western Ontario Chemistry Building, 1151 Richmond St. London, Ontario, Canada N6A 5B7 ; _publ_contact_author_name 'Ragogna, Paul' _publ_contact_author_email pragogna@uwo.ca _publ_section_title ; A new approach to internal Lewis pairs featuring a phosphenium acid and a pyridine base ; _publ_contact_author_address ;Department of Chemistry The University of Western Ontario Chemistry Building, 1151 Richmond St. London, Ontario, Canada N6A 5B7 ; _publ_contact_author_fax 519-661-3022 _publ_contact_author_phone '519-661-2111 x 87048' #TrackingRef '- Ragogna_clammy_submit.cif' _publ_requested_journal Che # Attachment '- CompiledCIF.cif' data_2Br _database_code_depnum_ccdc_archive 'CCDC 781898' #TrackingRef '- CompiledCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34.50 H27 Br Cl3 N3 P' _chemical_formula_weight 700.82 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 21.0725(6) _cell_length_b 14.0248(4) _cell_length_c 22.0431(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6514.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8630 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 24.95 _exptl_crystal_description square _exptl_crystal_colour red _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2848 _exptl_absorpt_coefficient_mu 1.586 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9249 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details ? _exptl_special_details ; One of the dichloromethane solvates contained disorder and had to be solved in two parts and left isotropic Hydrogen atoms could not be added to the disordered solvates ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 47195 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0712 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.43 _reflns_number_total 12975 _reflns_number_gt 9440 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1175P)^2^+1.9753P] 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' _refine_ls_abs_structure_Flack 0.046(11) _refine_ls_number_reflns 12975 _refine_ls_number_parameters 789 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1886 _refine_ls_wR_factor_gt 0.1712 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.001 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 Br1 Br 0.76090(3) 0.82495(5) 0.67563(3) 0.02768(18) Uani 1 1 d . . . Br2 Br 0.98924(3) 0.17476(5) 0.50175(3) 0.02594(17) Uani 1 1 d . . . P1 P 0.71223(9) 0.77724(15) 0.56716(9) 0.0222(4) Uani 1 1 d . . . P2 P 1.04010(8) 0.22343(15) 0.61041(8) 0.0201(4) Uani 1 1 d . . . N2 N 0.6946(3) 0.6614(4) 0.5777(3) 0.0207(12) Uani 1 1 d . . . N3 N 0.6470(3) 0.7058(5) 0.4154(3) 0.0251(14) Uani 1 1 d . . . C30 C 0.8877(3) 0.9566(5) 0.4421(4) 0.0302(17) Uani 1 1 d . . . H30A H 0.9112 1.0056 0.4226 0.036 Uiso 1 1 calc R . . N4 N 1.0578(3) 0.3390(4) 0.5996(3) 0.0209(12) Uani 1 1 d . . . N5 N 0.9729(4) 0.2539(3) 0.6484(3) 0.0173(17) Uani 1 1 d . . . N6 N 1.1057(3) 0.2912(4) 0.7575(3) 0.0245(13) Uani 1 1 d . . . C23 C 0.6038(4) 0.8833(6) 0.4522(4) 0.037(2) Uani 1 1 d . . . H23A H 0.5893 0.9441 0.4653 0.045 Uiso 1 1 calc R . . C22 C 0.5708(4) 0.8018(6) 0.4681(4) 0.0328(19) Uani 1 1 d . . . H22A H 0.5327 0.8066 0.4910 0.039 Uiso 1 1 calc R . . C21 C 0.5937(3) 0.7119(6) 0.4505(3) 0.0276(17) Uani 1 1 d . . . C20 C 0.5614(4) 0.6198(6) 0.4628(3) 0.0311(17) Uani 1 1 d . . . H20A H 0.5548 0.5861 0.4238 0.037 Uiso 1 1 calc R . . H20B H 0.5190 0.6331 0.4803 0.037 Uiso 1 1 calc R . . C19 C 0.5987(3) 0.5519(5) 0.5074(3) 0.0262(15) Uani 1 1 d . . . H19A H 0.5838 0.4856 0.5014 0.031 Uiso 1 1 calc R . . H19B H 0.6444 0.5539 0.4971 0.031 Uiso 1 1 calc R . . C18 C 0.5900(3) 0.5797(4) 0.5748(3) 0.0211(14) Uani 1 1 d . . . C13 C 0.6366(3) 0.6321(5) 0.6080(3) 0.0201(14) Uani 1 1 d . . . C2 C 0.7426(3) 0.5992(5) 0.5591(3) 0.0200(14) Uani 1 1 d . . . C3 C 0.7565(3) 0.4988(5) 0.5572(4) 0.0244(16) Uani 1 1 d . . . C8 C 0.8173(3) 0.4927(5) 0.5297(3) 0.0240(15) Uani 1 1 d . . . C7 C 0.8490(4) 0.4086(5) 0.5177(3) 0.0275(16) Uani 1 1 d . . . C6 C 0.8169(4) 0.3214(5) 0.5348(4) 0.0314(18) Uani 1 1 d . . . H6A H 0.8369 0.2615 0.5287 0.038 Uiso 1 1 calc R . . C9 C 0.9084(4) 0.4157(5) 0.4901(4) 0.0345(19) Uani 1 1 d . . . H9A H 0.9332 0.3601 0.4836 0.041 Uiso 1 1 calc R . . C5 C 0.7571(4) 0.3257(5) 0.5600(4) 0.036(2) Uani 1 1 d . . . H5A H 0.7358 0.2680 0.5694 0.044 Uiso 1 1 calc R . . C4 C 0.7259(4) 0.4152(5) 0.5724(4) 0.0318(19) Uani 1 1 d . . . H4A H 0.6852 0.4165 0.5908 0.038 Uiso 1 1 calc R . . N1 N 0.7782(4) 0.7463(4) 0.5293(3) 0.0232(19) Uani 1 1 d . . . C1 C 0.7914(3) 0.6498(5) 0.5322(3) 0.0212(15) Uani 1 1 d . . . C12 C 0.8408(3) 0.5842(5) 0.5128(3) 0.0224(16) Uani 1 1 d . . . C11 C 0.8983(3) 0.5887(5) 0.4847(3) 0.0263(16) Uani 1 1 d . . . H11A H 0.9157 0.6488 0.4739 0.032 Uiso 1 1 calc R . . C10 C 0.9315(4) 0.5053(6) 0.4719(4) 0.0344(19) Uani 1 1 d . . . H10A H 0.9705 0.5090 0.4505 0.041 Uiso 1 1 calc R . . C33 C 0.8181(3) 0.8147(4) 0.4979(3) 0.0165(13) Uani 1 1 d . . . C28 C 0.8228(3) 0.8148(5) 0.4357(3) 0.0233(15) Uani 1 1 d . . . C27 C 0.7926(4) 0.7392(5) 0.3944(4) 0.027(2) Uani 1 1 d . . . H27A H 0.7802 0.6836 0.4193 0.032 Uiso 1 1 calc R . . H27B H 0.8247 0.7174 0.3646 0.032 Uiso 1 1 calc R . . C26 C 0.7336(4) 0.7762(6) 0.3598(3) 0.0303(18) Uani 1 1 d . . . H26A H 0.7438 0.8384 0.3410 0.036 Uiso 1 1 calc R . . H26B H 0.7231 0.7310 0.3268 0.036 Uiso 1 1 calc R . . C24 C 0.6562(4) 0.8763(5) 0.4185(3) 0.0296(17) Uani 1 1 d . . . H24A H 0.6791 0.9319 0.4073 0.036 Uiso 1 1 calc R . . C14 C 0.6279(3) 0.6551(5) 0.6674(3) 0.0275(16) Uani 1 1 d . . . H14A H 0.6602 0.6886 0.6886 0.033 Uiso 1 1 calc R . . C15 C 0.5719(4) 0.6301(5) 0.6977(4) 0.0333(18) Uani 1 1 d . . . H15A H 0.5651 0.6491 0.7386 0.040 Uiso 1 1 calc R . . C16 C 0.5262(4) 0.5764(5) 0.6664(3) 0.0284(16) Uani 1 1 d . . . H16A H 0.4890 0.5549 0.6865 0.034 Uiso 1 1 calc R . . C17 C 0.5359(4) 0.5556(6) 0.6070(4) 0.0311(19) Uani 1 1 d . . . H17A H 0.5034 0.5222 0.5861 0.037 Uiso 1 1 calc R . . C29 C 0.8572(3) 0.8866(5) 0.4078(3) 0.0245(16) Uani 1 1 d . . . H29A H 0.8601 0.8882 0.3648 0.029 Uiso 1 1 calc R . . C31 C 0.8835(3) 0.9543(5) 0.5025(4) 0.0275(16) Uani 1 1 d . . . H31A H 0.9048 1.0017 0.5256 0.033 Uiso 1 1 calc R . . C32 C 0.8485(4) 0.8836(5) 0.5330(4) 0.0253(17) Uani 1 1 d . . . H32A H 0.8456 0.8829 0.5760 0.030 Uiso 1 1 calc R . . C56 C 1.1448(4) 0.1127(6) 0.7184(4) 0.0315(18) Uani 1 1 d . . . H56A H 1.1583 0.0515 0.7051 0.038 Uiso 1 1 calc R . . C57 C 1.1789(4) 0.1916(7) 0.7041(4) 0.037(2) Uani 1 1 d . . . H57A H 1.2170 0.1861 0.6812 0.044 Uiso 1 1 calc R . . C58 C 1.1576(4) 0.2802(7) 0.7231(3) 0.0297(18) Uani 1 1 d . . . C59 C 1.1940(4) 0.3721(6) 0.7090(4) 0.0350(19) Uani 1 1 d . . . H59A H 1.2349 0.3550 0.6898 0.042 Uiso 1 1 calc R . . H59B H 1.2036 0.4050 0.7476 0.042 Uiso 1 1 calc R . . C60 C 1.1585(4) 0.4422(5) 0.6668(3) 0.0296(17) Uani 1 1 d . . . H60A H 1.1134 0.4445 0.6792 0.036 Uiso 1 1 calc R . . H60B H 1.1764 0.5068 0.6726 0.036 Uiso 1 1 calc R . . C45 C 0.9964(3) 0.5031(5) 0.6202(3) 0.0227(16) Uani 1 1 d . . . C44 C 1.0273(4) 0.5862(5) 0.6052(3) 0.0270(18) Uani 1 1 d . . . H44A H 1.0688 0.5858 0.5883 0.032 Uiso 1 1 calc R . . C43 C 0.9943(4) 0.6725(5) 0.6162(4) 0.036(2) Uani 1 1 d . . . H43A H 1.0144 0.7306 0.6049 0.043 Uiso 1 1 calc R . . C42 C 0.9361(4) 0.6775(5) 0.6416(4) 0.037(2) Uani 1 1 d . . . H42A H 0.9166 0.7379 0.6474 0.045 Uiso 1 1 calc R . . C39 C 0.8429(4) 0.5845(6) 0.6905(4) 0.0346(19) Uani 1 1 d . . . H39A H 0.8194 0.6401 0.7006 0.042 Uiso 1 1 calc R . . C38 C 0.8199(3) 0.4983(5) 0.7044(4) 0.0309(18) Uani 1 1 d . . . H38A H 0.7788 0.4948 0.7220 0.037 Uiso 1 1 calc R . . C37 C 0.8539(4) 0.4102(6) 0.6940(3) 0.0297(18) Uani 1 1 d . . . H37A H 0.8374 0.3506 0.7069 0.036 Uiso 1 1 calc R . . C36 C 0.9108(3) 0.4169(4) 0.6649(3) 0.0202(15) Uani 1 1 d . . . C41 C 0.9354(3) 0.5075(5) 0.6480(3) 0.0232(16) Uani 1 1 d . . . C40 C 0.9035(4) 0.5930(5) 0.6599(4) 0.0291(17) Uani 1 1 d . . . C46 C 0.9334(3) 0.1866(4) 0.6792(4) 0.0213(14) Uani 1 1 d . . . C47 C 0.9024(3) 0.1180(5) 0.6440(3) 0.0229(16) Uani 1 1 d . . . H47A H 0.9061 0.1199 0.6011 0.027 Uiso 1 1 calc R . . C48 C 0.8662(3) 0.0471(5) 0.6714(4) 0.0281(17) Uani 1 1 d . . . H48A H 0.8464 -0.0011 0.6478 0.034 Uiso 1 1 calc R . . C49 C 0.8596(3) 0.0486(5) 0.7362(4) 0.0311(18) Uani 1 1 d . . . H49A H 0.8353 0.0005 0.7557 0.037 Uiso 1 1 calc R . . C50 C 0.8884(3) 0.1202(5) 0.7710(3) 0.0281(17) Uani 1 1 d . . . H50A H 0.8828 0.1208 0.8137 0.034 Uiso 1 1 calc R . . C51 C 0.9262(3) 0.1921(5) 0.7429(3) 0.0212(15) Uani 1 1 d . . . C52 C 0.9573(4) 0.2659(6) 0.7827(4) 0.0235(18) Uani 1 1 d . . . H52A H 0.9260 0.2881 0.8131 0.028 Uiso 1 1 calc R . . H52B H 0.9692 0.3214 0.7574 0.028 Uiso 1 1 calc R . . C53 C 1.0161(4) 0.2305(6) 0.8159(4) 0.0269(16) Uani 1 1 d . . . H53A H 1.0058 0.1701 0.8370 0.032 Uiso 1 1 calc R . . H53B H 1.0284 0.2779 0.8470 0.032 Uiso 1 1 calc R . . C54 C 1.0723(4) 0.2136(6) 0.7733(3) 0.0293(18) Uani 1 1 d . . . C55 C 1.0904(4) 0.1225(6) 0.7523(4) 0.0332(18) Uani 1 1 d . . . H55A H 1.0652 0.0682 0.7615 0.040 Uiso 1 1 calc R . . C62 C 1.2166(4) 0.4467(5) 0.5700(4) 0.0285(18) Uani 1 1 d . . . H62A H 1.2490 0.4811 0.5904 0.034 Uiso 1 1 calc R . . C63 C 1.2230(4) 0.4236(5) 0.5066(4) 0.0336(17) Uani 1 1 d . . . H63A H 1.2603 0.4422 0.4854 0.040 Uiso 1 1 calc R . . C64 C 1.1759(4) 0.3750(6) 0.4764(3) 0.0325(18) Uani 1 1 d . . . H64A H 1.1805 0.3606 0.4345 0.039 Uiso 1 1 calc R . . C65 C 1.1217(3) 0.3474(5) 0.5073(4) 0.0272(16) Uani 1 1 d . . . H65A H 1.0888 0.3140 0.4869 0.033 Uiso 1 1 calc R . . C35 C 0.9621(3) 0.3518(4) 0.6456(3) 0.0194(14) Uani 1 1 d . . . C34 C 1.0096(3) 0.3989(5) 0.6189(3) 0.0215(14) Uani 1 1 d . . . C66 C 1.1160(3) 0.3695(5) 0.5696(3) 0.0231(15) Uani 1 1 d . . . C25 C 0.6768(4) 0.7877(5) 0.4001(3) 0.0241(16) Uani 1 1 d . . . C61 C 1.1617(4) 0.4178(5) 0.6015(3) 0.0275(16) Uani 1 1 d . . . C200 C 0.2990(5) 0.2817(7) 0.3358(6) 0.071(3) Uani 1 1 d . . . H20C H 0.2647 0.2452 0.3558 0.085 Uiso 1 1 calc R . . H20D H 0.3094 0.2499 0.2969 0.085 Uiso 1 1 calc R . . Cl21 Cl 0.36657(16) 0.2850(2) 0.38274(15) 0.0809(9) Uani 1 1 d . . . Cl22 Cl 0.27369(19) 0.4008(2) 0.32206(16) 0.0935(11) Uani 1 1 d . . . C500 C 0.5497(6) 0.9779(13) 0.8049(6) 0.129(7) Uani 1 1 d . . . H50B H 0.5574 1.0371 0.7816 0.155 Uiso 1 1 calc R . . H50C H 0.5770 0.9798 0.8414 0.155 Uiso 1 1 calc R . . Cl51 Cl 0.5721(2) 0.8778(3) 0.75936(18) 0.1052(13) Uani 1 1 d . . . Cl52 Cl 0.4679(2) 0.9756(3) 0.82846(19) 0.1136(14) Uani 1 1 d . . . Cl92 Cl 0.4785(2) 0.5714(3) 0.8356(2) 0.0475(12) Uani 0.491(4) 1 d PD A 1 Cl93 Cl 0.3971(3) 0.7174(6) 0.7916(3) 0.093(2) Uani 0.491(4) 1 d PD A 1 C91 C 0.4594(8) 0.6938(7) 0.8420(8) 0.062(6) Uani 0.491(4) 1 d PD A 1 Cl95 Cl 0.2195(3) 0.5282(3) 0.8553(3) 0.0637(15) Uani 0.509(4) 1 d PDU A 2 Cl96 Cl 0.3174(3) 0.6292(4) 0.9236(3) 0.085(2) Uani 0.509(4) 1 d PDU A 2 C94 C 0.2919(6) 0.5203(9) 0.8891(8) 0.053(5) Uiso 0.509(4) 1 d PDU A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0303(4) 0.0219(3) 0.0308(4) -0.0004(3) 0.0000(3) -0.0010(3) Br2 0.0288(3) 0.0218(3) 0.0272(4) -0.0018(3) -0.0011(3) -0.0009(3) P1 0.0201(9) 0.0182(9) 0.0285(10) -0.0005(10) 0.0022(8) -0.0028(9) P2 0.0192(9) 0.0188(9) 0.0224(10) -0.0005(9) 0.0010(8) 0.0004(9) N2 0.023(3) 0.016(3) 0.023(3) -0.003(2) 0.005(2) 0.003(2) N3 0.023(3) 0.034(4) 0.018(3) -0.001(3) -0.006(3) -0.002(3) C30 0.023(4) 0.024(4) 0.044(5) 0.002(3) 0.010(3) -0.001(3) N4 0.019(3) 0.020(3) 0.023(3) 0.004(2) 0.000(2) -0.011(2) N5 0.020(4) 0.014(3) 0.018(4) 0.000(2) -0.004(3) -0.002(2) N6 0.024(3) 0.032(4) 0.018(3) 0.000(3) -0.004(3) -0.007(3) C23 0.047(5) 0.035(5) 0.030(4) -0.002(4) -0.013(4) 0.010(4) C22 0.029(4) 0.034(4) 0.036(5) -0.005(4) -0.009(4) 0.007(4) C21 0.025(4) 0.039(5) 0.020(4) -0.004(4) -0.003(3) -0.004(4) C20 0.031(4) 0.037(4) 0.025(4) 0.004(3) -0.004(3) -0.008(4) C19 0.026(4) 0.024(3) 0.028(4) 0.003(3) -0.002(3) -0.012(3) C18 0.022(3) 0.015(3) 0.027(4) 0.003(3) -0.006(3) -0.004(3) C13 0.018(3) 0.017(3) 0.025(4) 0.006(3) 0.000(3) -0.001(3) C2 0.017(3) 0.018(3) 0.024(4) -0.002(3) 0.001(3) -0.001(3) C3 0.027(4) 0.018(3) 0.028(4) 0.001(3) -0.006(3) -0.006(3) C8 0.023(4) 0.023(4) 0.027(4) -0.002(3) -0.004(3) -0.001(3) C7 0.030(4) 0.025(4) 0.027(4) -0.002(3) -0.006(3) 0.003(3) C6 0.040(5) 0.015(3) 0.039(5) 0.001(3) 0.004(4) 0.002(3) C9 0.035(4) 0.027(4) 0.042(5) -0.004(3) -0.007(4) 0.013(3) C5 0.045(5) 0.020(4) 0.044(5) 0.003(4) -0.003(4) -0.007(3) C4 0.034(5) 0.033(4) 0.028(4) 0.005(4) -0.001(4) -0.004(4) N1 0.023(4) 0.017(4) 0.029(5) -0.003(2) 0.001(4) -0.003(2) C1 0.019(4) 0.020(3) 0.025(4) 0.002(3) 0.002(3) -0.005(3) C12 0.019(3) 0.029(4) 0.019(4) 0.002(3) 0.001(3) 0.004(3) C11 0.018(4) 0.027(4) 0.034(4) -0.001(3) 0.000(3) 0.000(3) C10 0.023(4) 0.034(4) 0.047(5) 0.002(4) 0.004(4) 0.001(3) C33 0.015(3) 0.015(3) 0.019(3) 0.002(3) 0.004(3) -0.002(2) C28 0.021(3) 0.021(4) 0.028(4) -0.002(3) -0.006(3) 0.003(3) C27 0.027(5) 0.025(4) 0.028(5) -0.011(3) 0.010(4) -0.005(3) C26 0.040(5) 0.035(4) 0.015(4) 0.002(4) 0.007(4) -0.010(4) C24 0.034(4) 0.026(4) 0.028(4) 0.002(3) -0.005(3) -0.005(3) C14 0.026(4) 0.026(4) 0.031(4) -0.004(3) -0.003(3) -0.007(3) C15 0.034(4) 0.028(4) 0.038(5) 0.003(3) 0.010(4) 0.000(3) C16 0.028(4) 0.025(3) 0.031(4) 0.004(3) -0.002(3) -0.008(3) C17 0.016(4) 0.030(4) 0.047(5) -0.004(4) -0.005(4) -0.008(3) C29 0.024(4) 0.026(4) 0.023(4) 0.002(3) 0.010(3) -0.004(3) C31 0.023(4) 0.024(4) 0.036(4) -0.003(4) -0.001(4) -0.012(3) C32 0.030(4) 0.015(3) 0.030(4) -0.003(3) -0.004(3) -0.001(3) C56 0.031(4) 0.033(4) 0.031(4) -0.008(3) -0.005(3) 0.008(4) C57 0.020(4) 0.067(6) 0.024(4) -0.011(4) -0.006(3) 0.006(4) C58 0.021(4) 0.047(5) 0.021(4) 0.005(4) -0.013(3) -0.004(4) C59 0.026(4) 0.055(5) 0.024(4) -0.005(4) -0.005(3) -0.016(4) C60 0.030(4) 0.026(4) 0.033(4) -0.004(3) 0.000(3) -0.010(3) C45 0.030(4) 0.020(3) 0.018(4) -0.005(3) -0.001(3) 0.000(3) C44 0.045(5) 0.010(3) 0.026(4) -0.003(3) 0.004(3) -0.008(3) C43 0.059(6) 0.017(4) 0.030(4) -0.004(3) 0.004(4) -0.011(3) C42 0.057(6) 0.017(4) 0.039(5) -0.002(3) -0.011(4) 0.005(4) C39 0.034(4) 0.033(4) 0.036(5) -0.013(3) -0.010(4) 0.009(3) C38 0.022(4) 0.033(4) 0.038(4) -0.008(3) 0.000(3) 0.011(3) C37 0.028(4) 0.026(4) 0.035(5) 0.001(3) -0.005(3) 0.002(3) C36 0.022(4) 0.012(3) 0.026(4) 0.003(3) -0.004(3) 0.001(3) C41 0.031(4) 0.015(3) 0.023(4) 0.003(3) -0.004(3) -0.002(3) C40 0.029(4) 0.018(3) 0.040(5) -0.003(3) -0.009(3) 0.007(3) C46 0.016(3) 0.016(3) 0.032(4) 0.002(3) -0.003(3) -0.001(3) C47 0.019(4) 0.027(4) 0.023(4) -0.005(3) -0.001(3) 0.000(3) C48 0.019(4) 0.023(4) 0.042(5) -0.007(4) 0.000(4) 0.005(3) C49 0.018(4) 0.026(4) 0.049(5) -0.001(4) 0.009(3) -0.007(3) C50 0.024(4) 0.030(4) 0.030(4) 0.004(3) 0.003(3) 0.000(3) C51 0.013(3) 0.017(3) 0.033(4) 0.002(3) 0.005(3) -0.002(3) C52 0.027(5) 0.026(3) 0.018(4) -0.002(3) 0.002(4) 0.000(3) C53 0.021(4) 0.039(4) 0.021(4) 0.000(4) -0.004(3) -0.002(4) C54 0.028(4) 0.037(5) 0.024(4) 0.006(4) -0.014(3) -0.001(4) C55 0.037(4) 0.027(4) 0.035(4) 0.002(3) -0.013(4) 0.003(3) C62 0.026(4) 0.023(4) 0.036(4) 0.004(4) 0.008(3) -0.008(3) C63 0.026(4) 0.029(4) 0.046(5) 0.003(4) 0.011(4) -0.001(3) C64 0.039(5) 0.036(4) 0.023(4) -0.006(3) 0.007(3) 0.000(4) C65 0.025(4) 0.025(4) 0.031(4) -0.005(3) 0.006(3) -0.005(3) C35 0.022(4) 0.015(3) 0.022(4) -0.003(3) -0.003(3) 0.008(3) C34 0.020(3) 0.020(3) 0.024(4) 0.002(3) 0.001(3) 0.004(3) C66 0.024(4) 0.014(3) 0.031(4) 0.005(3) 0.004(3) -0.003(3) C25 0.028(4) 0.032(4) 0.012(3) -0.003(3) -0.008(3) -0.008(3) C61 0.032(4) 0.016(3) 0.035(4) 0.003(3) 0.004(3) 0.000(3) C200 0.070(7) 0.056(6) 0.087(8) -0.001(6) 0.006(6) 0.011(6) Cl21 0.092(2) 0.0720(19) 0.079(2) -0.0012(18) -0.0310(18) 0.0061(17) Cl22 0.131(3) 0.077(2) 0.073(2) 0.0133(17) -0.025(2) 0.026(2) C500 0.086(9) 0.25(2) 0.054(7) -0.065(10) 0.042(7) -0.095(11) Cl51 0.151(4) 0.072(2) 0.093(3) 0.0064(19) 0.015(3) 0.011(2) Cl52 0.145(4) 0.110(3) 0.086(3) -0.005(2) -0.015(3) 0.030(3) Cl92 0.057(3) 0.044(2) 0.041(2) -0.0027(19) 0.013(2) -0.010(2) Cl93 0.082(4) 0.102(5) 0.094(5) 0.045(4) -0.016(4) 0.011(4) C91 0.103(17) 0.045(10) 0.036(11) 0.011(9) -0.006(11) -0.014(11) Cl95 0.064(3) 0.038(2) 0.089(4) -0.014(3) -0.011(3) 0.003(2) Cl96 0.092(5) 0.066(4) 0.098(5) 0.021(3) -0.036(4) -0.018(3) _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 Br1 P1 2.686(2) . ? Br2 P2 2.711(2) . ? P1 N1 1.678(8) . ? P1 N2 1.683(6) . ? P2 N4 1.681(6) . ? P2 N5 1.700(8) . ? N2 C2 1.397(8) . ? N2 C13 1.453(8) . ? N3 C25 1.352(9) . ? N3 C21 1.366(10) . ? C30 C31 1.335(12) . ? C30 C29 1.396(10) . ? C30 H30A 0.9500 . ? N4 C34 1.385(9) . ? N4 C66 1.457(8) . ? N5 C35 1.393(8) . ? N5 C46 1.430(9) . ? N6 C58 1.340(10) . ? N6 C54 1.341(10) . ? C23 C24 1.335(11) . ? C23 C22 1.384(12) . ? C23 H23A 0.9500 . ? C22 C21 1.405(11) . ? C22 H22A 0.9500 . ? C21 C20 1.485(11) . ? C20 C19 1.579(10) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C19 C18 1.547(10) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C18 C17 1.385(10) . ? C18 C13 1.428(9) . ? C13 C14 1.362(10) . ? C2 C1 1.383(9) . ? C2 C3 1.439(9) . ? C3 C4 1.378(10) . ? C3 C8 1.420(10) . ? C8 C7 1.382(10) . ? C8 C12 1.425(10) . ? C7 C9 1.396(11) . ? C7 C6 1.448(10) . ? C6 C5 1.377(11) . ? C6 H6A 0.9500 . ? C9 C10 1.405(11) . ? C9 H9A 0.9500 . ? C5 C4 1.444(11) . ? C5 H5A 0.9500 . ? C4 H4A 0.9500 . ? N1 C1 1.384(8) . ? N1 C33 1.452(9) . ? C1 C12 1.453(10) . ? C12 C11 1.361(9) . ? C11 C10 1.393(10) . ? C11 H11A 0.9500 . ? C10 H10A 0.9500 . ? C33 C28 1.375(10) . ? C33 C32 1.393(9) . ? C28 C29 1.385(10) . ? C28 C27 1.536(10) . ? C27 C26 1.549(12) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C26 C25 1.499(11) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C24 C25 1.378(11) . ? C24 H24A 0.9500 . ? C14 C15 1.400(10) . ? C14 H14A 0.9500 . ? C15 C16 1.405(11) . ? C15 H15A 0.9500 . ? C16 C17 1.357(12) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C29 H29A 0.9500 . ? C31 C32 1.406(10) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? C56 C57 1.356(12) . ? C56 C55 1.375(11) . ? C56 H56A 0.9500 . ? C57 C58 1.387(12) . ? C57 H57A 0.9500 . ? C58 C59 1.532(12) . ? C59 C60 1.546(11) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C60 C61 1.481(11) . ? C60 H60A 0.9900 . ? C60 H60B 0.9900 . ? C45 C44 1.376(10) . ? C45 C41 1.425(10) . ? C45 C34 1.488(9) . ? C44 C43 1.416(11) . ? C44 H44A 0.9500 . ? C43 C42 1.351(12) . ? C43 H43A 0.9500 . ? C42 C40 1.427(11) . ? C42 H42A 0.9500 . ? C39 C38 1.337(11) . ? C39 C40 1.450(11) . ? C39 H39A 0.9500 . ? C38 C37 1.447(10) . ? C38 H38A 0.9500 . ? C37 C36 1.363(10) . ? C37 H37A 0.9500 . ? C36 C41 1.423(9) . ? C36 C35 1.476(9) . ? C41 C40 1.399(10) . ? C46 C47 1.398(10) . ? C46 C51 1.414(11) . ? C47 C48 1.391(10) . ? C47 H47A 0.9500 . ? C48 C49 1.434(12) . ? C48 H48A 0.9500 . ? C49 C50 1.402(10) . ? C49 H49A 0.9500 . ? C50 C51 1.426(10) . ? C50 H50A 0.9500 . ? C51 C52 1.507(10) . ? C52 C53 1.523(11) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.530(11) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 C55 1.412(11) . ? C55 H55A 0.9500 . ? C62 C61 1.408(10) . ? C62 C63 1.442(12) . ? C62 H62A 0.9500 . ? C63 C64 1.376(11) . ? C63 H63A 0.9500 . ? C64 C65 1.385(10) . ? C64 H64A 0.9500 . ? C65 C66 1.414(11) . ? C65 H65A 0.9500 . ? C35 C34 1.335(10) . ? C66 C61 1.372(10) . ? C200 Cl21 1.761(12) . ? C200 Cl22 1.779(11) . ? C200 H20C 0.9900 . ? C200 H20D 0.9900 . ? C500 Cl51 1.791(15) . ? C500 Cl52 1.799(12) . ? C500 H50B 0.9900 . ? C500 H50C 0.9900 . ? Cl92 C91 1.769(9) . ? Cl93 C91 1.751(9) . ? Cl95 C94 1.700(9) . ? Cl96 C94 1.789(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 N2 90.1(3) . . ? N1 P1 Br1 101.0(3) . . ? N2 P1 Br1 101.7(2) . . ? N4 P2 N5 90.7(3) . . ? N4 P2 Br2 101.8(2) . . ? N5 P2 Br2 99.7(2) . . ? C2 N2 C13 124.6(5) . . ? C2 N2 P1 113.8(4) . . ? C13 N2 P1 121.4(4) . . ? C25 N3 C21 118.1(7) . . ? C31 C30 C29 119.6(7) . . ? C31 C30 H30A 120.2 . . ? C29 C30 H30A 120.2 . . ? C34 N4 C66 125.4(5) . . ? C34 N4 P2 112.2(4) . . ? C66 N4 P2 122.2(4) . . ? C35 N5 C46 125.2(7) . . ? C35 N5 P2 111.2(5) . . ? C46 N5 P2 123.6(4) . . ? C58 N6 C54 118.7(7) . . ? C24 C23 C22 119.8(8) . . ? C24 C23 H23A 120.1 . . ? C22 C23 H23A 120.1 . . ? C23 C22 C21 119.9(9) . . ? C23 C22 H22A 120.1 . . ? C21 C22 H22A 120.1 . . ? N3 C21 C22 119.7(8) . . ? N3 C21 C20 115.2(7) . . ? C22 C21 C20 124.9(8) . . ? C21 C20 C19 114.2(6) . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C18 C19 C20 112.7(6) . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? C18 C19 H19B 109.0 . . ? C20 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C17 C18 C13 115.4(6) . . ? C17 C18 C19 121.9(6) . . ? C13 C18 C19 122.7(6) . . ? C14 C13 C18 121.5(6) . . ? C14 C13 N2 119.3(6) . . ? C18 C13 N2 119.2(6) . . ? C1 C2 N2 110.1(6) . . ? C1 C2 C3 109.8(6) . . ? N2 C2 C3 140.0(6) . . ? C4 C3 C8 118.3(7) . . ? C4 C3 C2 137.0(7) . . ? C8 C3 C2 104.7(6) . . ? C7 C8 C3 124.7(7) . . ? C7 C8 C12 123.4(7) . . ? C3 C8 C12 111.9(6) . . ? C8 C7 C9 117.1(7) . . ? C8 C7 C6 116.5(7) . . ? C9 C7 C6 126.4(7) . . ? C5 C6 C7 119.6(7) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C7 C9 C10 119.9(7) . . ? C7 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C6 C5 C4 122.1(7) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C3 C4 C5 118.7(8) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C1 N1 C33 123.4(7) . . ? C1 N1 P1 113.4(5) . . ? C33 N1 P1 123.1(4) . . ? C2 C1 N1 111.8(6) . . ? C2 C1 C12 109.5(6) . . ? N1 C1 C12 138.6(7) . . ? C11 C12 C8 118.1(7) . . ? C11 C12 C1 137.9(7) . . ? C8 C12 C1 104.1(6) . . ? C12 C11 C10 120.0(7) . . ? C12 C11 H11A 120.0 . . ? C10 C11 H11A 120.0 . . ? C11 C10 C9 121.3(7) . . ? C11 C10 H10A 119.3 . . ? C9 C10 H10A 119.3 . . ? C28 C33 C32 121.3(6) . . ? C28 C33 N1 121.2(6) . . ? C32 C33 N1 117.4(6) . . ? C33 C28 C29 118.8(6) . . ? C33 C28 C27 124.1(7) . . ? C29 C28 C27 117.1(7) . . ? C28 C27 C26 113.2(6) . . ? C28 C27 H27A 108.9 . . ? C26 C27 H27A 108.9 . . ? C28 C27 H27B 108.9 . . ? C26 C27 H27B 108.9 . . ? H27A C27 H27B 107.8 . . ? C25 C26 C27 112.6(6) . . ? C25 C26 H26A 109.1 . . ? C27 C26 H26A 109.1 . . ? C25 C26 H26B 109.1 . . ? C27 C26 H26B 109.1 . . ? H26A C26 H26B 107.8 . . ? C23 C24 C25 119.4(7) . . ? C23 C24 H24A 120.3 . . ? C25 C24 H24A 120.3 . . ? C13 C14 C15 120.9(7) . . ? C13 C14 H14A 119.6 . . ? C15 C14 H14A 119.6 . . ? C14 C15 C16 118.5(7) . . ? C14 C15 H15A 120.7 . . ? C16 C15 H15A 120.7 . . ? C17 C16 C15 119.0(7) . . ? C17 C16 H16A 120.5 . . ? C15 C16 H16A 120.5 . . ? C16 C17 C18 124.6(7) . . ? C16 C17 H17A 117.7 . . ? C18 C17 H17A 117.7 . . ? C28 C29 C30 120.7(7) . . ? C28 C29 H29A 119.6 . . ? C30 C29 H29A 119.6 . . ? C30 C31 C32 121.8(7) . . ? C30 C31 H31A 119.1 . . ? C32 C31 H31A 119.1 . . ? C33 C32 C31 117.8(7) . . ? C33 C32 H32A 121.1 . . ? C31 C32 H32A 121.1 . . ? C57 C56 C55 119.1(8) . . ? C57 C56 H56A 120.4 . . ? C55 C56 H56A 120.4 . . ? C56 C57 C58 119.3(8) . . ? C56 C57 H57A 120.4 . . ? C58 C57 H57A 120.4 . . ? N6 C58 C57 122.7(8) . . ? N6 C58 C59 115.3(8) . . ? C57 C58 C59 122.0(8) . . ? C58 C59 C60 114.5(6) . . ? C58 C59 H59A 108.6 . . ? C60 C59 H59A 108.6 . . ? C58 C59 H59B 108.6 . . ? C60 C59 H59B 108.6 . . ? H59A C59 H59B 107.6 . . ? C61 C60 C59 114.5(6) . . ? C61 C60 H60A 108.6 . . ? C59 C60 H60A 108.6 . . ? C61 C60 H60B 108.6 . . ? C59 C60 H60B 108.6 . . ? H60A C60 H60B 107.6 . . ? C44 C45 C41 119.5(7) . . ? C44 C45 C34 137.7(7) . . ? C41 C45 C34 102.7(6) . . ? C45 C44 C43 116.8(8) . . ? C45 C44 H44A 121.6 . . ? C43 C44 H44A 121.6 . . ? C42 C43 C44 124.1(7) . . ? C42 C43 H43A 118.0 . . ? C44 C43 H43A 118.0 . . ? C43 C42 C40 120.8(7) . . ? C43 C42 H42A 119.6 . . ? C40 C42 H42A 119.6 . . ? C38 C39 C40 120.0(7) . . ? C38 C39 H39A 120.0 . . ? C40 C39 H39A 120.0 . . ? C39 C38 C37 123.7(7) . . ? C39 C38 H38A 118.1 . . ? C37 C38 H38A 118.1 . . ? C36 C37 C38 116.9(7) . . ? C36 C37 H37A 121.5 . . ? C38 C37 H37A 121.5 . . ? C37 C36 C41 120.3(6) . . ? C37 C36 C35 137.5(6) . . ? C41 C36 C35 102.2(6) . . ? C40 C41 C36 122.8(7) . . ? C40 C41 C45 123.5(7) . . ? C36 C41 C45 113.7(6) . . ? C41 C40 C42 115.3(7) . . ? C41 C40 C39 116.1(7) . . ? C42 C40 C39 128.6(7) . . ? C47 C46 C51 122.6(6) . . ? C47 C46 N5 117.5(7) . . ? C51 C46 N5 119.9(6) . . ? C48 C47 C46 120.5(7) . . ? C48 C47 H47A 119.7 . . ? C46 C47 H47A 119.7 . . ? C47 C48 C49 118.3(7) . . ? C47 C48 H48A 120.8 . . ? C49 C48 H48A 120.8 . . ? C50 C49 C48 120.9(7) . . ? C50 C49 H49A 119.6 . . ? C48 C49 H49A 119.6 . . ? C49 C50 C51 120.7(7) . . ? C49 C50 H50A 119.6 . . ? C51 C50 H50A 119.6 . . ? C46 C51 C50 116.9(6) . . ? C46 C51 C52 124.7(6) . . ? C50 C51 C52 118.4(7) . . ? C51 C52 C53 114.2(7) . . ? C51 C52 H52A 108.7 . . ? C53 C52 H52A 108.7 . . ? C51 C52 H52B 108.7 . . ? C53 C52 H52B 108.7 . . ? H52A C52 H52B 107.6 . . ? C52 C53 C54 112.7(6) . . ? C52 C53 H53A 109.0 . . ? C54 C53 H53A 109.0 . . ? C52 C53 H53B 109.0 . . ? C54 C53 H53B 109.0 . . ? H53A C53 H53B 107.8 . . ? N6 C54 C55 120.6(8) . . ? N6 C54 C53 116.1(8) . . ? C55 C54 C53 123.4(7) . . ? C56 C55 C54 119.5(8) . . ? C56 C55 H55A 120.2 . . ? C54 C55 H55A 120.2 . . ? C61 C62 C63 119.4(7) . . ? C61 C62 H62A 120.3 . . ? C63 C62 H62A 120.3 . . ? C64 C63 C62 120.8(7) . . ? C64 C63 H63A 119.6 . . ? C62 C63 H63A 119.6 . . ? C63 C64 C65 119.7(7) . . ? C63 C64 H64A 120.1 . . ? C65 C64 H64A 120.1 . . ? C64 C65 C66 119.2(7) . . ? C64 C65 H65A 120.4 . . ? C66 C65 H65A 120.4 . . ? C34 C35 N5 112.6(6) . . ? C34 C35 C36 111.7(6) . . ? N5 C35 C36 135.7(7) . . ? C35 C34 N4 112.7(6) . . ? C35 C34 C45 109.7(6) . . ? N4 C34 C45 137.6(6) . . ? C61 C66 C65 123.1(6) . . ? C61 C66 N4 120.3(6) . . ? C65 C66 N4 116.6(6) . . ? N3 C25 C24 123.1(7) . . ? N3 C25 C26 115.3(7) . . ? C24 C25 C26 121.5(7) . . ? C66 C61 C62 117.8(7) . . ? C66 C61 C60 125.5(7) . . ? C62 C61 C60 116.8(7) . . ? Cl21 C200 Cl22 108.5(6) . . ? Cl21 C200 H20C 110.0 . . ? Cl22 C200 H20C 110.0 . . ? Cl21 C200 H20D 110.0 . . ? Cl22 C200 H20D 110.0 . . ? H20C C200 H20D 108.4 . . ? Cl51 C500 Cl52 113.6(7) . . ? Cl51 C500 H50B 108.8 . . ? Cl52 C500 H50B 108.8 . . ? Cl51 C500 H50C 108.8 . . ? Cl52 C500 H50C 108.8 . . ? H50B C500 H50C 107.7 . . ? Cl93 C91 Cl92 107.7(7) . . ? Cl95 C94 Cl96 113.6(7) . . ? 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 N1 P1 N2 C2 7.6(6) . . . . ? Br1 P1 N2 C2 -93.7(5) . . . . ? N1 P1 N2 C13 -177.2(6) . . . . ? Br1 P1 N2 C13 81.5(5) . . . . ? N5 P2 N4 C34 -6.4(5) . . . . ? Br2 P2 N4 C34 93.6(5) . . . . ? N5 P2 N4 C66 177.1(6) . . . . ? Br2 P2 N4 C66 -82.9(5) . . . . ? N4 P2 N5 C35 6.9(5) . . . . ? Br2 P2 N5 C35 -95.2(5) . . . . ? N4 P2 N5 C46 -172.7(6) . . . . ? Br2 P2 N5 C46 85.2(6) . . . . ? C24 C23 C22 C21 2.2(12) . . . . ? C25 N3 C21 C22 1.4(10) . . . . ? C25 N3 C21 C20 176.8(6) . . . . ? C23 C22 C21 N3 -2.8(11) . . . . ? C23 C22 C21 C20 -177.7(7) . . . . ? N3 C21 C20 C19 70.8(8) . . . . ? C22 C21 C20 C19 -114.1(8) . . . . ? C21 C20 C19 C18 79.9(8) . . . . ? C20 C19 C18 C17 79.1(8) . . . . ? C20 C19 C18 C13 -100.6(7) . . . . ? C17 C18 C13 C14 0.7(10) . . . . ? C19 C18 C13 C14 -179.6(6) . . . . ? C17 C18 C13 N2 -179.4(6) . . . . ? C19 C18 C13 N2 0.4(9) . . . . ? C2 N2 C13 C14 110.4(8) . . . . ? P1 N2 C13 C14 -64.4(8) . . . . ? C2 N2 C13 C18 -69.6(9) . . . . ? P1 N2 C13 C18 115.7(6) . . . . ? C13 N2 C2 C1 -179.6(6) . . . . ? P1 N2 C2 C1 -4.5(8) . . . . ? C13 N2 C2 C3 3.4(13) . . . . ? P1 N2 C2 C3 178.5(8) . . . . ? C1 C2 C3 C4 -175.0(9) . . . . ? N2 C2 C3 C4 2.1(17) . . . . ? C1 C2 C3 C8 2.1(8) . . . . ? N2 C2 C3 C8 179.2(8) . . . . ? C4 C3 C8 C7 -1.1(12) . . . . ? C2 C3 C8 C7 -178.8(7) . . . . ? C4 C3 C8 C12 175.9(7) . . . . ? C2 C3 C8 C12 -1.8(8) . . . . ? C3 C8 C7 C9 179.7(7) . . . . ? C12 C8 C7 C9 3.0(11) . . . . ? C3 C8 C7 C6 0.1(11) . . . . ? C12 C8 C7 C6 -176.6(7) . . . . ? C8 C7 C6 C5 1.7(11) . . . . ? C9 C7 C6 C5 -177.8(8) . . . . ? C8 C7 C9 C10 -4.4(11) . . . . ? C6 C7 C9 C10 175.1(8) . . . . ? C7 C6 C5 C4 -2.7(13) . . . . ? C8 C3 C4 C5 0.2(11) . . . . ? C2 C3 C4 C5 177.0(9) . . . . ? C6 C5 C4 C3 1.7(13) . . . . ? N2 P1 N1 C1 -8.8(6) . . . . ? Br1 P1 N1 C1 93.1(5) . . . . ? N2 P1 N1 C33 172.8(6) . . . . ? Br1 P1 N1 C33 -85.3(6) . . . . ? N2 C2 C1 N1 -2.1(8) . . . . ? C3 C2 C1 N1 175.9(6) . . . . ? N2 C2 C1 C12 -179.7(6) . . . . ? C3 C2 C1 C12 -1.7(8) . . . . ? C33 N1 C1 C2 -173.7(7) . . . . ? P1 N1 C1 C2 7.9(8) . . . . ? C33 N1 C1 C12 2.9(14) . . . . ? P1 N1 C1 C12 -175.6(8) . . . . ? C7 C8 C12 C11 -1.6(11) . . . . ? C3 C8 C12 C11 -178.7(6) . . . . ? C7 C8 C12 C1 177.9(7) . . . . ? C3 C8 C12 C1 0.8(8) . . . . ? C2 C1 C12 C11 179.9(8) . . . . ? N1 C1 C12 C11 3.3(16) . . . . ? C2 C1 C12 C8 0.6(8) . . . . ? N1 C1 C12 C8 -176.1(9) . . . . ? C8 C12 C11 C10 1.6(11) . . . . ? C1 C12 C11 C10 -177.7(8) . . . . ? C12 C11 C10 C9 -3.2(12) . . . . ? C7 C9 C10 C11 4.6(12) . . . . ? C1 N1 C33 C28 69.4(10) . . . . ? P1 N1 C33 C28 -112.3(7) . . . . ? C1 N1 C33 C32 -114.5(8) . . . . ? P1 N1 C33 C32 63.8(9) . . . . ? C32 C33 C28 C29 -1.6(10) . . . . ? N1 C33 C28 C29 174.5(6) . . . . ? C32 C33 C28 C27 177.8(7) . . . . ? N1 C33 C28 C27 -6.2(10) . . . . ? C33 C28 C27 C26 106.3(8) . . . . ? C29 C28 C27 C26 -74.4(9) . . . . ? C28 C27 C26 C25 -73.1(9) . . . . ? C22 C23 C24 C25 -0.2(11) . . . . ? C18 C13 C14 C15 -1.6(11) . . . . ? N2 C13 C14 C15 178.4(6) . . . . ? C13 C14 C15 C16 3.2(11) . . . . ? C14 C15 C16 C17 -4.0(11) . . . . ? C15 C16 C17 C18 3.4(12) . . . . ? C13 C18 C17 C16 -1.6(11) . . . . ? C19 C18 C17 C16 178.6(7) . . . . ? C33 C28 C29 C30 1.2(10) . . . . ? C27 C28 C29 C30 -178.1(7) . . . . ? C31 C30 C29 C28 -0.1(11) . . . . ? C29 C30 C31 C32 -0.8(12) . . . . ? C28 C33 C32 C31 0.8(10) . . . . ? N1 C33 C32 C31 -175.4(6) . . . . ? C30 C31 C32 C33 0.4(11) . . . . ? C55 C56 C57 C58 -1.1(11) . . . . ? C54 N6 C58 C57 -1.3(10) . . . . ? C54 N6 C58 C59 -178.1(6) . . . . ? C56 C57 C58 N6 2.9(11) . . . . ? C56 C57 C58 C59 179.5(7) . . . . ? N6 C58 C59 C60 -68.2(8) . . . . ? C57 C58 C59 C60 114.9(8) . . . . ? C58 C59 C60 C61 -79.9(9) . . . . ? C41 C45 C44 C43 -2.9(11) . . . . ? C34 C45 C44 C43 -178.6(8) . . . . ? C45 C44 C43 C42 1.9(12) . . . . ? C44 C43 C42 C40 0.4(13) . . . . ? C40 C39 C38 C37 3.9(12) . . . . ? C39 C38 C37 C36 -4.3(12) . . . . ? C38 C37 C36 C41 2.3(10) . . . . ? C38 C37 C36 C35 178.3(8) . . . . ? C37 C36 C41 C40 -0.1(11) . . . . ? C35 C36 C41 C40 -177.4(7) . . . . ? C37 C36 C41 C45 177.6(7) . . . . ? C35 C36 C41 C45 0.3(8) . . . . ? C44 C45 C41 C40 1.8(11) . . . . ? C34 C45 C41 C40 178.8(7) . . . . ? C44 C45 C41 C36 -175.9(7) . . . . ? C34 C45 C41 C36 1.2(8) . . . . ? C36 C41 C40 C42 178.0(7) . . . . ? C45 C41 C40 C42 0.5(11) . . . . ? C36 C41 C40 C39 -0.3(11) . . . . ? C45 C41 C40 C39 -177.8(7) . . . . ? C43 C42 C40 C41 -1.6(12) . . . . ? C43 C42 C40 C39 176.5(8) . . . . ? C38 C39 C40 C41 -1.5(11) . . . . ? C38 C39 C40 C42 -179.6(8) . . . . ? C35 N5 C46 C47 115.5(8) . . . . ? P2 N5 C46 C47 -65.0(8) . . . . ? C35 N5 C46 C51 -63.6(10) . . . . ? P2 N5 C46 C51 115.9(7) . . . . ? C51 C46 C47 C48 -4.7(11) . . . . ? N5 C46 C47 C48 176.3(6) . . . . ? C46 C47 C48 C49 2.5(11) . . . . ? C47 C48 C49 C50 0.5(11) . . . . ? C48 C49 C50 C51 -1.3(11) . . . . ? C47 C46 C51 C50 3.7(10) . . . . ? N5 C46 C51 C50 -177.3(6) . . . . ? C47 C46 C51 C52 -178.5(7) . . . . ? N5 C46 C51 C52 0.5(10) . . . . ? C49 C50 C51 C46 -0.7(10) . . . . ? C49 C50 C51 C52 -178.6(7) . . . . ? C46 C51 C52 C53 -100.6(9) . . . . ? C50 C51 C52 C53 77.1(9) . . . . ? C51 C52 C53 C54 70.1(9) . . . . ? C58 N6 C54 C55 -2.0(10) . . . . ? C58 N6 C54 C53 176.3(6) . . . . ? C52 C53 C54 N6 80.9(8) . . . . ? C52 C53 C54 C55 -100.9(8) . . . . ? C57 C56 C55 C54 -2.1(11) . . . . ? N6 C54 C55 C56 3.8(11) . . . . ? C53 C54 C55 C56 -174.4(7) . . . . ? C61 C62 C63 C64 1.0(11) . . . . ? C62 C63 C64 C65 -0.4(12) . . . . ? C63 C64 C65 C66 -0.2(11) . . . . ? C46 N5 C35 C34 173.8(7) . . . . ? P2 N5 C35 C34 -5.7(8) . . . . ? C46 N5 C35 C36 -6.3(13) . . . . ? P2 N5 C35 C36 174.1(7) . . . . ? C37 C36 C35 C34 -178.4(8) . . . . ? C41 C36 C35 C34 -1.9(8) . . . . ? C37 C36 C35 N5 1.7(15) . . . . ? C41 C36 C35 N5 178.2(8) . . . . ? N5 C35 C34 N4 0.9(9) . . . . ? C36 C35 C34 N4 -179.0(6) . . . . ? N5 C35 C34 C45 -177.3(6) . . . . ? C36 C35 C34 C45 2.8(8) . . . . ? C66 N4 C34 C35 -179.3(6) . . . . ? P2 N4 C34 C35 4.4(8) . . . . ? C66 N4 C34 C45 -1.7(13) . . . . ? P2 N4 C34 C45 -178.1(7) . . . . ? C44 C45 C34 C35 173.8(9) . . . . ? C41 C45 C34 C35 -2.4(8) . . . . ? C44 C45 C34 N4 -3.8(16) . . . . ? C41 C45 C34 N4 -180.0(8) . . . . ? C64 C65 C66 C61 0.2(11) . . . . ? C64 C65 C66 N4 179.6(6) . . . . ? C34 N4 C66 C61 70.6(9) . . . . ? P2 N4 C66 C61 -113.4(6) . . . . ? C34 N4 C66 C65 -108.8(8) . . . . ? P2 N4 C66 C65 67.1(8) . . . . ? C21 N3 C25 C24 0.6(10) . . . . ? C21 N3 C25 C26 -177.8(6) . . . . ? C23 C24 C25 N3 -1.2(11) . . . . ? C23 C24 C25 C26 177.1(7) . . . . ? C27 C26 C25 N3 -76.2(8) . . . . ? C27 C26 C25 C24 105.4(8) . . . . ? C65 C66 C61 C62 0.3(10) . . . . ? N4 C66 C61 C62 -179.1(6) . . . . ? C65 C66 C61 C60 -179.5(7) . . . . ? N4 C66 C61 C60 1.1(11) . . . . ? C63 C62 C61 C66 -0.9(11) . . . . ? C63 C62 C61 C60 178.9(7) . . . . ? C59 C60 C61 C66 97.2(9) . . . . ? C59 C60 C61 C62 -82.6(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.783 _refine_diff_density_min -0.887 _refine_diff_density_rms 0.120 data_2[OTf] _database_code_depnum_ccdc_archive 'CCDC 781899' #TrackingRef '- CompiledCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H25 F3 N3 O3 P S' _chemical_formula_weight 643.60 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 15.975(3) _cell_length_b 16.350(3) _cell_length_c 16.581(3) _cell_angle_alpha 117.72(3) _cell_angle_beta 105.64(3) _cell_angle_gamma 103.78(3) _cell_volume 3338.7(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 58471 _cell_measurement_theta_min 1.59 _cell_measurement_theta_max 26.38 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9613 _exptl_absorpt_correction_T_max 0.9727 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2008)' _exptl_special_details ; # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.000 507 124 ' ' _platon_squeeze_details #Disordered solvate could not be modelled, squeeze function was employed ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 58471 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 26.38 _reflns_number_total 13625 _reflns_number_gt 8824 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0877P)^2^+0.9525P] 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_number_reflns 13625 _refine_ls_number_parameters 811 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1790 _refine_ls_wR_factor_gt 0.1647 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 P2 P 0.24040(6) 0.61248(5) 0.36665(5) 0.03285(19) Uani 1 1 d . . . S2 S 0.07064(5) 0.71305(5) 0.30367(5) 0.03230(18) Uani 1 1 d . . . P1 P 0.54620(6) 0.86044(6) 0.17746(7) 0.0397(2) Uani 1 1 d . . . N5 N 0.16014(17) 0.48929(16) 0.28687(16) 0.0315(5) Uani 1 1 d . . . F6 F -0.11371(14) 0.65188(18) 0.20044(15) 0.0711(6) Uani 1 1 d . . . F5 F -0.03100(17) 0.81296(18) 0.28451(16) 0.0741(7) Uani 1 1 d . . . F4 F -0.06255(16) 0.7451(2) 0.36252(16) 0.0739(7) Uani 1 1 d . . . N4 N 0.22518(18) 0.61637(16) 0.46435(16) 0.0371(6) Uani 1 1 d . . . N2 N 0.61815(16) 0.81347(17) 0.21783(19) 0.0365(6) Uani 1 1 d . . . C46 C 0.13597(19) 0.4284(2) 0.17966(19) 0.0306(6) Uani 1 1 d . . . N1 N 0.45174(17) 0.74524(18) 0.10938(19) 0.0377(6) Uani 1 1 d . . . O5 O 0.14029(16) 0.80236(18) 0.40051(16) 0.0576(6) Uani 1 1 d . . . C13 C 0.7203(2) 0.8785(2) 0.2875(2) 0.0366(7) Uani 1 1 d . . . N6 N 0.3961(2) 0.5092(2) 0.4102(2) 0.0627(9) Uani 1 1 d . . . C68 C -0.0397(2) 0.7306(3) 0.2868(2) 0.0463(8) Uani 1 1 d . . . N3 N 0.4930(2) 0.88337(19) 0.3771(2) 0.0488(7) Uani 1 1 d . . . C48 C 0.0629(2) 0.3974(2) 0.0158(2) 0.0395(7) Uani 1 1 d . . . H48A H 0.0318 0.4155 -0.0265 0.047 Uiso 1 1 calc R . . C47 C 0.0895(2) 0.4557(2) 0.1192(2) 0.0343(7) Uani 1 1 d . . . H47A H 0.0761 0.5136 0.1483 0.041 Uiso 1 1 calc R . . C3 C 0.5936(2) 0.6339(2) 0.1874(2) 0.0410(7) Uani 1 1 d . . . C8 C 0.5041(2) 0.5459(2) 0.1211(2) 0.0413(7) Uani 1 1 d . . . C37 C -0.0079(2) 0.2604(2) 0.2219(2) 0.0411(8) Uani 1 1 d . . . H37A H -0.0090 0.2415 0.1580 0.049 Uiso 1 1 calc R . . C36 C 0.0496(2) 0.3574(2) 0.3068(2) 0.0426(8) Uani 1 1 d . . . C51 C 0.1599(2) 0.3458(2) 0.1416(2) 0.0360(7) Uani 1 1 d . . . C14 C 0.7778(2) 0.9088(2) 0.2479(3) 0.0422(8) Uani 1 1 d . . . H14A H 0.7518 0.8848 0.1783 0.051 Uiso 1 1 calc R . . C1 C 0.4754(2) 0.6734(2) 0.1169(2) 0.0374(7) Uani 1 1 d . . . C35 C 0.1204(2) 0.4531(2) 0.3333(2) 0.0376(7) Uani 1 1 d . . . C66 C 0.2775(2) 0.7039(2) 0.5701(2) 0.0427(8) Uani 1 1 d . . . C2 C 0.5709(2) 0.7132(2) 0.1812(2) 0.0369(7) Uani 1 1 d . . . C33 C 0.3549(2) 0.7288(2) 0.0542(3) 0.0461(8) Uani 1 1 d . . . C49 C 0.0821(2) 0.3124(3) -0.0253(2) 0.0452(8) Uani 1 1 d . . . H49A H 0.0619 0.2707 -0.0964 0.054 Uiso 1 1 calc R . . C11 C 0.3388(2) 0.4861(2) 0.0094(3) 0.0464(8) Uani 1 1 d . . . H11A H 0.2870 0.4970 -0.0213 0.056 Uiso 1 1 calc R . . C50 C 0.1305(2) 0.2879(2) 0.0369(2) 0.0464(8) Uani 1 1 d . . . H50A H 0.1442 0.2301 0.0075 0.056 Uiso 1 1 calc R . . C12 C 0.4281(2) 0.5642(2) 0.0750(2) 0.0420(7) Uani 1 1 d . . . C7 C 0.4913(2) 0.4502(2) 0.1032(2) 0.0453(8) Uani 1 1 d . . . C9 C 0.3974(3) 0.3696(2) 0.0326(3) 0.0500(9) Uani 1 1 d . . . H9A H 0.3850 0.3027 0.0165 0.060 Uiso 1 1 calc R . . C15 C 0.8740(2) 0.9749(2) 0.3127(3) 0.0488(9) Uani 1 1 d . . . H15A H 0.9149 0.9967 0.2875 0.059 Uiso 1 1 calc R . . C18 C 0.7541(2) 0.9089(2) 0.3878(2) 0.0407(7) Uani 1 1 d . . . C52 C 0.2188(2) 0.3204(2) 0.2067(2) 0.0477(9) Uani 1 1 d . . . H52A H 0.1941 0.2453 0.1702 0.057 Uiso 1 1 calc R . . H52B H 0.2114 0.3470 0.2703 0.057 Uiso 1 1 calc R . . C34 C 0.1577(2) 0.5264(2) 0.4359(2) 0.0426(8) Uani 1 1 d . . . C6 C 0.5736(3) 0.4452(3) 0.1570(3) 0.0515(9) Uani 1 1 d . . . H6A H 0.5689 0.3822 0.1480 0.062 Uiso 1 1 calc R . . C5 C 0.6590(3) 0.5295(3) 0.2213(3) 0.0546(9) Uani 1 1 d . . . H5A H 0.7125 0.5235 0.2561 0.066 Uiso 1 1 calc R . . C65 C 0.2538(2) 0.7855(2) 0.5989(2) 0.0421(8) Uani 1 1 d . . . H65A H 0.2072 0.7864 0.5501 0.051 Uiso 1 1 calc R . . C41 C 0.0498(3) 0.3824(2) 0.4010(2) 0.0502(9) Uani 1 1 d . . . C38 C -0.0659(3) 0.1887(2) 0.2322(3) 0.0529(9) Uani 1 1 d . . . H38A H -0.1067 0.1214 0.1737 0.063 Uiso 1 1 calc R . . C64 C 0.2991(3) 0.8663(2) 0.7006(3) 0.0546(9) Uani 1 1 d . . . H64A H 0.2835 0.9231 0.7216 0.066 Uiso 1 1 calc R . . C54 C 0.3775(2) 0.4804(2) 0.3135(3) 0.0546(10) Uani 1 1 d . . . C10 C 0.3254(2) 0.3873(2) -0.0120(3) 0.0494(8) Uani 1 1 d . . . H10A H 0.2638 0.3318 -0.0593 0.059 Uiso 1 1 calc R . . C4 C 0.6718(2) 0.6268(3) 0.2388(3) 0.0497(8) Uani 1 1 d . . . H4A H 0.7322 0.6845 0.2843 0.060 Uiso 1 1 calc R . . C40 C -0.0059(3) 0.3129(2) 0.4130(3) 0.0528(9) Uani 1 1 d . . . C45 C 0.1146(3) 0.4849(2) 0.4839(2) 0.0500(9) Uani 1 1 d . . . C44 C 0.1230(3) 0.5184(3) 0.5792(2) 0.0598(11) Uani 1 1 d . . . H44A H 0.1660 0.5863 0.6353 0.072 Uiso 1 1 calc R . . C61 C 0.3460(3) 0.6996(2) 0.6388(2) 0.0572(10) Uani 1 1 d . . . C19 C 0.6935(2) 0.8750(2) 0.4328(3) 0.0496(8) Uani 1 1 d . . . H19A H 0.7312 0.8599 0.4778 0.060 Uiso 1 1 calc R . . H19B H 0.6359 0.8109 0.3769 0.060 Uiso 1 1 calc R . . C16 C 0.9102(2) 1.0091(2) 0.4135(3) 0.0531(9) Uani 1 1 d . . . H16A H 0.9758 1.0557 0.4580 0.064 Uiso 1 1 calc R . . C25 C 0.4188(3) 0.8889(2) 0.3224(3) 0.0549(10) Uani 1 1 d . . . C23 C 0.5229(3) 1.0519(3) 0.3671(3) 0.0631(11) Uani 1 1 d . . . H23A H 0.5336 1.1090 0.3627 0.076 Uiso 1 1 calc R . . C20 C 0.6609(3) 0.9541(3) 0.4936(3) 0.0559(9) Uani 1 1 d . . . H20A H 0.6396 0.9362 0.5363 0.067 Uiso 1 1 calc R . . H20B H 0.7168 1.0218 0.5396 0.067 Uiso 1 1 calc R . . C26 C 0.3211(2) 0.8029(3) 0.2730(3) 0.0579(10) Uani 1 1 d . . . H26A H 0.2713 0.8251 0.2533 0.070 Uiso 1 1 calc R . . H26B H 0.3137 0.7893 0.3235 0.070 Uiso 1 1 calc R . . C60 C 0.3756(4) 0.6137(3) 0.6097(3) 0.0894(18) Uani 1 1 d . . . H60A H 0.3219 0.5506 0.5471 0.107 Uiso 1 1 calc R . . H60B H 0.3888 0.6020 0.6644 0.107 Uiso 1 1 calc R . . C17 C 0.8512(2) 0.9757(2) 0.4508(3) 0.0490(8) Uani 1 1 d . . . H17A H 0.8776 0.9988 0.5202 0.059 Uiso 1 1 calc R . . C39 C -0.0653(3) 0.2131(2) 0.3233(3) 0.0596(10) Uani 1 1 d . . . H39A H -0.1052 0.1625 0.3266 0.072 Uiso 1 1 calc R . . C22 C 0.5982(3) 1.0471(3) 0.4261(3) 0.0580(10) Uani 1 1 d . . . H22A H 0.6608 1.1014 0.4638 0.070 Uiso 1 1 calc R . . C21 C 0.5818(3) 0.9621(2) 0.4302(3) 0.0538(9) Uani 1 1 d . . . C53 C 0.3255(2) 0.3658(2) 0.2331(3) 0.0572(10) Uani 1 1 d . . . H53A H 0.3572 0.3312 0.2577 0.069 Uiso 1 1 calc R . . H53B H 0.3317 0.3517 0.1706 0.069 Uiso 1 1 calc R . . C27 C 0.3032(2) 0.7024(3) 0.1782(3) 0.0546(10) Uani 1 1 d . . . H27A H 0.3597 0.6874 0.1938 0.065 Uiso 1 1 calc R . . H27B H 0.2470 0.6460 0.1624 0.065 Uiso 1 1 calc R . . C32 C 0.3379(3) 0.7399(3) -0.0259(3) 0.0598(10) Uani 1 1 d . . . H32A H 0.3882 0.7585 -0.0428 0.072 Uiso 1 1 calc R . . C63 C 0.3660(3) 0.8644(3) 0.7705(2) 0.0615(11) Uani 1 1 d . . . H63A H 0.3957 0.9195 0.8402 0.074 Uiso 1 1 calc R . . C42 C 0.0044(3) 0.3498(3) 0.5131(3) 0.0614(11) Uani 1 1 d . . . H42A H -0.0317 0.3054 0.5254 0.074 Uiso 1 1 calc R . . C59 C 0.4657(4) 0.6345(3) 0.5913(3) 0.102(2) Uani 1 1 d . . . H59A H 0.5108 0.7075 0.6422 0.122 Uiso 1 1 calc R . . H59B H 0.4979 0.5935 0.6026 0.122 Uiso 1 1 calc R . . C24 C 0.4302(3) 0.9722(3) 0.3134(3) 0.0632(11) Uani 1 1 d . . . H24A H 0.3772 0.9743 0.2726 0.076 Uiso 1 1 calc R . . C62 C 0.3906(3) 0.7834(3) 0.7408(2) 0.0642(11) Uani 1 1 d . . . H62A H 0.4384 0.7842 0.7902 0.077 Uiso 1 1 calc R . . C58 C 0.4462(3) 0.6105(3) 0.4859(3) 0.0749(14) Uani 1 1 d . . . C28 C 0.2852(2) 0.7056(3) 0.0853(3) 0.0568(10) Uani 1 1 d . . . C56 C 0.4551(3) 0.6534(3) 0.3676(4) 0.0706(12) Uani 1 1 d . . . H56A H 0.4748 0.7026 0.3532 0.085 Uiso 1 1 calc R . . C43 C 0.0656(3) 0.4486(3) 0.5919(3) 0.0645(11) Uani 1 1 d . . . H43A H 0.0699 0.4715 0.6577 0.077 Uiso 1 1 calc R . . C57 C 0.4760(3) 0.6831(3) 0.4665(4) 0.0827(16) Uani 1 1 d . . . H57A H 0.5108 0.7533 0.5209 0.099 Uiso 1 1 calc R . . C55 C 0.4047(2) 0.5498(3) 0.2901(3) 0.0626(11) Uani 1 1 d . . . H55A H 0.3892 0.5272 0.2216 0.075 Uiso 1 1 calc R . . C29 C 0.1923(3) 0.6878(4) 0.0267(4) 0.0831(14) Uani 1 1 d . . . H29A H 0.1416 0.6693 0.0432 0.100 Uiso 1 1 calc R . . C31 C 0.2451(3) 0.7233(4) -0.0810(4) 0.0850(14) Uani 1 1 d . . . H31A H 0.2315 0.7301 -0.1364 0.102 Uiso 1 1 calc R . . C30 C 0.1737(3) 0.6970(4) -0.0547(4) 0.0973(17) Uani 1 1 d . . . H30A H 0.1105 0.6849 -0.0928 0.117 Uiso 1 1 calc R . . S1 S 0.66079(8) 0.88727(8) 0.98657(9) 0.0634(3) Uani 1 1 d . . . O4 O 0.08345(15) 0.70144(17) 0.21733(15) 0.0449(5) Uani 1 1 d . . . O6 O 0.04603(17) 0.62151(17) 0.30216(18) 0.0515(6) Uani 1 1 d . . . F1 F 0.6047(3) 0.9929(2) 0.9252(3) 0.1442(16) Uani 1 1 d . . . O2 O 0.7357(2) 0.8566(2) 0.9889(3) 0.1042(12) Uani 1 1 d . . . F2 F 0.7537(3) 1.0302(3) 0.9758(3) 0.182(2) Uani 1 1 d . . . O1 O 0.5692(2) 0.8142(4) 0.9313(5) 0.177(3) Uani 1 1 d . . . O3 O 0.6845(4) 0.9683(4) 1.0902(3) 0.162(2) Uani 1 1 d . . . C67 C 0.6691(4) 0.9574(4) 0.9312(4) 0.0912(17) Uani 1 1 d . . . F3 F 0.6531(4) 0.8932(4) 0.8345(3) 0.220(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P2 0.0418(4) 0.0272(4) 0.0250(4) 0.0164(3) 0.0089(3) 0.0111(3) S2 0.0326(4) 0.0395(4) 0.0261(4) 0.0188(3) 0.0128(3) 0.0170(3) P1 0.0351(4) 0.0315(4) 0.0589(5) 0.0275(4) 0.0223(4) 0.0176(3) N5 0.0394(14) 0.0276(12) 0.0230(11) 0.0155(10) 0.0066(10) 0.0131(10) F6 0.0347(11) 0.0980(17) 0.0534(13) 0.0312(12) 0.0097(10) 0.0247(11) F5 0.1008(18) 0.0878(16) 0.0709(14) 0.0519(13) 0.0425(13) 0.0744(15) F4 0.0700(14) 0.132(2) 0.0587(13) 0.0593(14) 0.0476(12) 0.0675(15) N4 0.0516(15) 0.0240(11) 0.0213(11) 0.0135(10) 0.0052(11) 0.0059(11) N2 0.0287(13) 0.0289(12) 0.0540(16) 0.0231(12) 0.0193(12) 0.0149(10) C46 0.0316(15) 0.0318(14) 0.0198(13) 0.0129(12) 0.0067(11) 0.0102(12) N1 0.0297(13) 0.0350(13) 0.0555(16) 0.0282(12) 0.0193(12) 0.0184(11) O5 0.0458(14) 0.0562(14) 0.0384(12) 0.0136(11) 0.0034(11) 0.0202(11) C13 0.0233(14) 0.0246(14) 0.056(2) 0.0185(14) 0.0168(14) 0.0107(12) N6 0.0589(18) 0.0380(15) 0.0465(17) 0.0068(13) -0.0114(14) 0.0318(14) C68 0.049(2) 0.064(2) 0.0385(18) 0.0313(17) 0.0226(16) 0.0341(18) N3 0.0445(16) 0.0371(14) 0.079(2) 0.0323(15) 0.0418(16) 0.0230(13) C48 0.0364(17) 0.0555(19) 0.0288(15) 0.0257(15) 0.0114(13) 0.0225(15) C47 0.0348(16) 0.0409(16) 0.0294(15) 0.0214(13) 0.0118(13) 0.0190(13) C3 0.0340(16) 0.0341(16) 0.0533(19) 0.0226(15) 0.0171(15) 0.0195(13) C8 0.0386(17) 0.0315(15) 0.0514(19) 0.0227(15) 0.0155(15) 0.0180(13) C37 0.0481(19) 0.0263(14) 0.0308(15) 0.0136(13) 0.0049(14) 0.0089(13) C36 0.054(2) 0.0297(15) 0.0314(16) 0.0193(13) 0.0067(14) 0.0085(14) C51 0.0376(17) 0.0316(15) 0.0293(15) 0.0151(13) 0.0068(13) 0.0143(13) C14 0.0392(18) 0.0373(16) 0.064(2) 0.0345(16) 0.0253(16) 0.0208(14) C1 0.0274(15) 0.0307(15) 0.0541(19) 0.0242(14) 0.0162(14) 0.0141(12) C35 0.0508(19) 0.0267(14) 0.0237(14) 0.0164(12) 0.0056(13) 0.0074(13) C66 0.062(2) 0.0235(14) 0.0202(14) 0.0111(12) 0.0060(14) 0.0011(14) C2 0.0313(16) 0.0321(15) 0.0507(18) 0.0241(14) 0.0187(14) 0.0164(13) C33 0.0332(17) 0.0354(16) 0.070(2) 0.0315(17) 0.0163(16) 0.0198(14) C49 0.0422(18) 0.055(2) 0.0239(15) 0.0149(14) 0.0103(14) 0.0206(16) C11 0.0340(17) 0.0379(17) 0.059(2) 0.0276(16) 0.0126(16) 0.0116(14) C50 0.0434(19) 0.0385(17) 0.0345(17) 0.0099(14) 0.0072(14) 0.0185(15) C12 0.0358(17) 0.0353(16) 0.057(2) 0.0276(15) 0.0176(15) 0.0178(14) C7 0.056(2) 0.0324(16) 0.054(2) 0.0260(15) 0.0239(17) 0.0244(15) C9 0.061(2) 0.0273(15) 0.061(2) 0.0255(16) 0.0270(18) 0.0169(15) C15 0.0368(18) 0.0417(18) 0.084(3) 0.0418(19) 0.0327(19) 0.0210(15) C18 0.0321(16) 0.0314(15) 0.053(2) 0.0192(15) 0.0218(15) 0.0127(13) C52 0.055(2) 0.0277(15) 0.0367(17) 0.0117(13) 0.0002(15) 0.0199(14) C34 0.061(2) 0.0258(14) 0.0274(15) 0.0177(13) 0.0098(14) 0.0051(14) C6 0.065(2) 0.0401(18) 0.060(2) 0.0316(17) 0.0255(19) 0.0326(18) C5 0.058(2) 0.057(2) 0.065(2) 0.0386(19) 0.0251(19) 0.0413(19) C65 0.0483(19) 0.0273(15) 0.0342(16) 0.0151(13) 0.0148(14) 0.0008(13) C41 0.068(2) 0.0307(16) 0.0308(16) 0.0206(14) 0.0066(16) 0.0013(15) C38 0.058(2) 0.0267(16) 0.046(2) 0.0160(15) 0.0073(17) 0.0060(15) C64 0.060(2) 0.0316(17) 0.044(2) 0.0118(15) 0.0206(18) 0.0014(16) C54 0.0414(19) 0.0400(18) 0.054(2) 0.0137(16) -0.0002(16) 0.0283(15) C10 0.0444(19) 0.0296(16) 0.056(2) 0.0195(15) 0.0153(16) 0.0075(14) C4 0.0389(18) 0.0478(19) 0.060(2) 0.0292(17) 0.0153(16) 0.0248(15) C40 0.065(2) 0.0362(17) 0.0456(19) 0.0293(16) 0.0132(17) 0.0050(16) C45 0.074(2) 0.0318(16) 0.0250(15) 0.0187(13) 0.0088(15) 0.0046(16) C44 0.087(3) 0.0384(18) 0.0292(17) 0.0213(15) 0.0122(17) 0.0011(18) C61 0.082(3) 0.0296(16) 0.0297(16) 0.0184(14) 0.0004(17) 0.0047(16) C19 0.0433(19) 0.0445(18) 0.052(2) 0.0222(16) 0.0229(16) 0.0157(15) C16 0.0273(17) 0.0426(18) 0.078(3) 0.0307(19) 0.0170(18) 0.0132(14) C25 0.053(2) 0.0408(18) 0.094(3) 0.040(2) 0.053(2) 0.0277(17) C23 0.080(3) 0.0380(19) 0.100(3) 0.040(2) 0.070(3) 0.0304(19) C20 0.048(2) 0.047(2) 0.058(2) 0.0196(17) 0.0283(18) 0.0156(17) C26 0.044(2) 0.059(2) 0.097(3) 0.050(2) 0.045(2) 0.0322(17) C60 0.126(4) 0.040(2) 0.038(2) 0.0182(17) -0.026(2) 0.022(2) C17 0.0346(18) 0.0433(18) 0.055(2) 0.0198(16) 0.0175(16) 0.0157(15) C39 0.067(2) 0.0345(18) 0.063(2) 0.0315(18) 0.016(2) 0.0058(17) C22 0.059(2) 0.0397(19) 0.083(3) 0.0296(19) 0.050(2) 0.0225(17) C21 0.054(2) 0.0376(18) 0.071(2) 0.0219(17) 0.045(2) 0.0198(16) C53 0.057(2) 0.0402(18) 0.0447(19) 0.0106(15) -0.0002(16) 0.0314(17) C27 0.0285(17) 0.050(2) 0.099(3) 0.049(2) 0.0307(18) 0.0198(15) C32 0.057(2) 0.055(2) 0.078(3) 0.044(2) 0.022(2) 0.0320(18) C63 0.077(3) 0.0339(18) 0.0279(17) 0.0063(15) 0.0109(18) -0.0045(17) C42 0.077(3) 0.046(2) 0.050(2) 0.0370(18) 0.0161(19) 0.0032(18) C59 0.115(4) 0.048(2) 0.052(2) -0.0022(19) -0.037(3) 0.052(3) C24 0.065(2) 0.061(2) 0.102(3) 0.052(2) 0.059(2) 0.047(2) C62 0.085(3) 0.0413(19) 0.0253(16) 0.0175(15) -0.0012(17) -0.0004(19) C58 0.064(2) 0.0386(19) 0.060(2) 0.0044(17) -0.0186(19) 0.0320(18) C28 0.0361(19) 0.050(2) 0.096(3) 0.051(2) 0.0232(19) 0.0210(16) C56 0.0346(19) 0.048(2) 0.101(3) 0.029(2) 0.014(2) 0.0224(17) C43 0.090(3) 0.059(2) 0.0378(19) 0.0362(18) 0.0215(19) 0.011(2) C57 0.048(2) 0.037(2) 0.085(3) 0.006(2) -0.020(2) 0.0203(17) C55 0.043(2) 0.052(2) 0.078(3) 0.027(2) 0.0178(19) 0.0316(18) C29 0.040(2) 0.094(3) 0.138(4) 0.081(3) 0.031(3) 0.038(2) C31 0.070(3) 0.096(3) 0.108(4) 0.077(3) 0.021(3) 0.044(3) C30 0.052(3) 0.124(4) 0.140(5) 0.099(4) 0.022(3) 0.045(3) S1 0.0689(7) 0.0615(6) 0.1012(8) 0.0601(6) 0.0499(6) 0.0444(5) O4 0.0433(13) 0.0698(15) 0.0404(12) 0.0387(12) 0.0265(10) 0.0267(11) O6 0.0636(15) 0.0558(14) 0.0640(15) 0.0445(13) 0.0375(13) 0.0344(12) F1 0.129(3) 0.082(2) 0.159(3) 0.089(2) -0.027(2) 0.0120(19) O2 0.0645(19) 0.0692(19) 0.145(3) 0.038(2) 0.033(2) 0.0434(16) F2 0.116(3) 0.128(3) 0.205(4) 0.124(3) -0.024(3) -0.045(2) O1 0.0486(19) 0.176(4) 0.360(7) 0.230(5) 0.030(3) 0.026(2) O3 0.270(6) 0.245(5) 0.100(3) 0.115(4) 0.132(4) 0.206(5) C67 0.077(3) 0.062(3) 0.066(3) 0.031(2) -0.004(2) -0.018(3) F3 0.233(5) 0.260(6) 0.071(2) 0.076(3) 0.062(3) 0.008(4) _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 P2 N4 1.677(2) . ? P2 N5 1.681(3) . ? S2 O5 1.424(3) . ? S2 O4 1.432(2) . ? S2 O6 1.440(2) . ? S2 C68 1.821(3) . ? P1 N2 1.686(2) . ? P1 N1 1.688(3) . ? N5 C35 1.362(4) . ? N5 C46 1.449(3) . ? F6 C68 1.324(4) . ? F5 C68 1.340(4) . ? F4 C68 1.334(4) . ? N4 C34 1.368(4) . ? N4 C66 1.459(4) . ? N2 C2 1.365(4) . ? N2 C13 1.463(4) . ? C46 C47 1.388(4) . ? C46 C51 1.397(4) . ? N1 C1 1.364(4) . ? N1 C33 1.453(4) . ? C13 C18 1.387(4) . ? C13 C14 1.389(4) . ? N6 C58 1.361(4) . ? N6 C54 1.362(5) . ? N3 C25 1.335(5) . ? N3 C21 1.358(4) . ? C48 C47 1.385(4) . ? C48 C49 1.387(4) . ? C48 H48A 0.9500 . ? C47 H47A 0.9500 . ? C3 C4 1.373(4) . ? C3 C8 1.422(4) . ? C3 C2 1.467(4) . ? C8 C7 1.400(4) . ? C8 C12 1.425(4) . ? C37 C36 1.368(4) . ? C37 C38 1.419(4) . ? C37 H37A 0.9500 . ? C36 C41 1.419(4) . ? C36 C35 1.472(4) . ? C51 C50 1.396(4) . ? C51 C52 1.509(4) . ? C14 C15 1.386(5) . ? C14 H14A 0.9500 . ? C1 C2 1.376(4) . ? C1 C12 1.470(4) . ? C35 C34 1.379(4) . ? C66 C65 1.376(5) . ? C66 C61 1.391(5) . ? C33 C32 1.387(5) . ? C33 C28 1.393(5) . ? C49 C50 1.387(4) . ? C49 H49A 0.9500 . ? C11 C12 1.360(4) . ? C11 C10 1.428(4) . ? C11 H11A 0.9500 . ? C50 H50A 0.9500 . ? C7 C6 1.421(5) . ? C7 C9 1.425(5) . ? C9 C10 1.363(5) . ? C9 H9A 0.9500 . ? C15 C16 1.378(5) . ? C15 H15A 0.9500 . ? C18 C17 1.395(4) . ? C18 C19 1.524(5) . ? C52 C53 1.529(5) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C34 C45 1.464(4) . ? C6 C5 1.361(5) . ? C6 H6A 0.9500 . ? C5 C4 1.427(4) . ? C5 H5A 0.9500 . ? C65 C64 1.387(4) . ? C65 H65A 0.9500 . ? C41 C40 1.395(4) . ? C41 C45 1.426(4) . ? C38 C39 1.367(5) . ? C38 H38A 0.9500 . ? C64 C63 1.366(5) . ? C64 H64A 0.9500 . ? C54 C55 1.376(5) . ? C54 C53 1.522(4) . ? C10 H10A 0.9500 . ? C4 H4A 0.9500 . ? C40 C39 1.421(5) . ? C40 C42 1.421(5) . ? C45 C44 1.363(4) . ? C44 C43 1.420(5) . ? C44 H44A 0.9500 . ? C61 C62 1.406(4) . ? C61 C60 1.497(6) . ? C19 C20 1.533(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C16 C17 1.397(5) . ? C16 H16A 0.9500 . ? C25 C24 1.413(5) . ? C25 C26 1.509(5) . ? C23 C22 1.376(6) . ? C23 C24 1.405(5) . ? C23 H23A 0.9500 . ? C20 C21 1.487(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C26 C27 1.543(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C60 C59 1.542(8) . ? C60 H60A 0.9900 . ? C60 H60B 0.9900 . ? C17 H17A 0.9500 . ? C39 H39A 0.9500 . ? C22 C21 1.387(5) . ? C22 H22A 0.9500 . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C27 C28 1.516(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C32 C31 1.397(5) . ? C32 H32A 0.9500 . ? C63 C62 1.377(6) . ? C63 H63A 0.9500 . ? C42 C43 1.366(5) . ? C42 H42A 0.9500 . ? C59 C58 1.520(7) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C24 H24A 0.9500 . ? C62 H62A 0.9500 . ? C58 C57 1.380(6) . ? C28 C29 1.408(5) . ? C56 C57 1.387(6) . ? C56 C55 1.391(5) . ? C56 H56A 0.9500 . ? C43 H43A 0.9500 . ? C57 H57A 0.9500 . ? C55 H55A 0.9500 . ? C29 C30 1.388(6) . ? C29 H29A 0.9500 . ? C31 C30 1.372(7) . ? C31 H31A 0.9500 . ? C30 H30A 0.9500 . ? S1 O1 1.354(4) . ? S1 O2 1.402(3) . ? S1 O3 1.464(4) . ? S1 C67 1.774(5) . ? F1 C67 1.300(7) . ? F2 C67 1.291(5) . ? C67 F3 1.350(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 N4 P2 N5 90.54(12) . . ? O5 S2 O4 116.61(15) . . ? O5 S2 O6 113.46(15) . . ? O4 S2 O6 114.48(14) . . ? O5 S2 C68 104.10(15) . . ? O4 S2 C68 103.44(14) . . ? O6 S2 C68 102.43(16) . . ? N2 P1 N1 89.97(12) . . ? C35 N5 C46 123.7(2) . . ? C35 N5 P2 113.13(18) . . ? C46 N5 P2 123.14(19) . . ? C34 N4 C66 121.5(2) . . ? C34 N4 P2 113.05(19) . . ? C66 N4 P2 125.45(19) . . ? C2 N2 C13 125.6(2) . . ? C2 N2 P1 113.40(19) . . ? C13 N2 P1 120.95(18) . . ? C47 C46 C51 122.9(3) . . ? C47 C46 N5 117.7(2) . . ? C51 C46 N5 119.4(2) . . ? C1 N1 C33 124.8(2) . . ? C1 N1 P1 113.21(19) . . ? C33 N1 P1 121.94(19) . . ? C18 C13 C14 123.7(3) . . ? C18 C13 N2 119.9(3) . . ? C14 C13 N2 116.4(3) . . ? C58 N6 C54 117.9(4) . . ? F6 C68 F4 108.0(3) . . ? F6 C68 F5 106.5(3) . . ? F4 C68 F5 106.3(3) . . ? F6 C68 S2 112.2(2) . . ? F4 C68 S2 112.2(2) . . ? F5 C68 S2 111.2(2) . . ? C25 N3 C21 119.6(3) . . ? C47 C48 C49 119.4(3) . . ? C47 C48 H48A 120.3 . . ? C49 C48 H48A 120.3 . . ? C48 C47 C46 119.2(3) . . ? C48 C47 H47A 120.4 . . ? C46 C47 H47A 120.4 . . ? C4 C3 C8 119.4(3) . . ? C4 C3 C2 137.6(3) . . ? C8 C3 C2 103.0(2) . . ? C7 C8 C3 123.2(3) . . ? C7 C8 C12 122.9(3) . . ? C3 C8 C12 113.8(3) . . ? C36 C37 C38 118.0(3) . . ? C36 C37 H37A 121.0 . . ? C38 C37 H37A 121.0 . . ? C37 C36 C41 119.3(3) . . ? C37 C36 C35 137.4(3) . . ? C41 C36 C35 103.3(2) . . ? C50 C51 C46 116.2(3) . . ? C50 C51 C52 119.5(3) . . ? C46 C51 C52 124.2(3) . . ? C15 C14 C13 118.3(3) . . ? C15 C14 H14A 120.8 . . ? C13 C14 H14A 120.8 . . ? N1 C1 C2 111.8(2) . . ? N1 C1 C12 138.2(3) . . ? C2 C1 C12 110.0(3) . . ? N5 C35 C34 111.7(2) . . ? N5 C35 C36 138.8(3) . . ? C34 C35 C36 109.6(3) . . ? C65 C66 C61 122.6(3) . . ? C65 C66 N4 118.5(3) . . ? C61 C66 N4 118.7(3) . . ? N2 C2 C1 111.5(3) . . ? N2 C2 C3 138.1(3) . . ? C1 C2 C3 110.3(2) . . ? C32 C33 C28 123.5(3) . . ? C32 C33 N1 117.4(3) . . ? C28 C33 N1 119.1(3) . . ? C48 C49 C50 120.4(3) . . ? C48 C49 H49A 119.8 . . ? C50 C49 H49A 119.8 . . ? C12 C11 C10 118.0(3) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? C49 C50 C51 121.8(3) . . ? C49 C50 H50A 119.1 . . ? C51 C50 H50A 119.1 . . ? C11 C12 C8 119.7(3) . . ? C11 C12 C1 137.4(3) . . ? C8 C12 C1 102.9(3) . . ? C8 C7 C6 116.1(3) . . ? C8 C7 C9 116.0(3) . . ? C6 C7 C9 127.9(3) . . ? C10 C9 C7 120.7(3) . . ? C10 C9 H9A 119.6 . . ? C7 C9 H9A 119.6 . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15A 120.0 . . ? C14 C15 H15A 120.0 . . ? C13 C18 C17 116.4(3) . . ? C13 C18 C19 124.9(3) . . ? C17 C18 C19 118.7(3) . . ? C51 C52 C53 112.4(3) . . ? C51 C52 H52A 109.1 . . ? C53 C52 H52A 109.1 . . ? C51 C52 H52B 109.1 . . ? C53 C52 H52B 109.1 . . ? H52A C52 H52B 107.9 . . ? N4 C34 C35 111.6(3) . . ? N4 C34 C45 138.0(3) . . ? C35 C34 C45 110.4(2) . . ? C5 C6 C7 120.7(3) . . ? C5 C6 H6A 119.6 . . ? C7 C6 H6A 119.6 . . ? C6 C5 C4 123.0(3) . . ? C6 C5 H5A 118.5 . . ? C4 C5 H5A 118.5 . . ? C66 C65 C64 118.9(3) . . ? C66 C65 H65A 120.6 . . ? C64 C65 H65A 120.6 . . ? C40 C41 C36 123.6(3) . . ? C40 C41 C45 122.6(3) . . ? C36 C41 C45 113.8(3) . . ? C39 C38 C37 122.4(3) . . ? C39 C38 H38A 118.8 . . ? C37 C38 H38A 118.8 . . ? C63 C64 C65 120.3(3) . . ? C63 C64 H64A 119.9 . . ? C65 C64 H64A 119.9 . . ? N6 C54 C55 122.5(3) . . ? N6 C54 C53 115.3(3) . . ? C55 C54 C53 122.2(4) . . ? C9 C10 C11 122.6(3) . . ? C9 C10 H10A 118.7 . . ? C11 C10 H10A 118.7 . . ? C3 C4 C5 117.6(3) . . ? C3 C4 H4A 121.2 . . ? C5 C4 H4A 121.2 . . ? C41 C40 C39 115.6(3) . . ? C41 C40 C42 116.4(3) . . ? C39 C40 C42 128.0(3) . . ? C44 C45 C41 119.8(3) . . ? C44 C45 C34 137.2(3) . . ? C41 C45 C34 103.0(2) . . ? C45 C44 C43 118.0(3) . . ? C45 C44 H44A 121.0 . . ? C43 C44 H44A 121.0 . . ? C66 C61 C62 116.6(3) . . ? C66 C61 C60 124.1(3) . . ? C62 C61 C60 119.3(3) . . ? C18 C19 C20 113.9(3) . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19B 108.8 . . ? C20 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C15 C16 C17 120.4(3) . . ? C15 C16 H16A 119.8 . . ? C17 C16 H16A 119.8 . . ? N3 C25 C24 122.0(3) . . ? N3 C25 C26 116.5(3) . . ? C24 C25 C26 121.4(4) . . ? C22 C23 C24 119.9(3) . . ? C22 C23 H23A 120.0 . . ? C24 C23 H23A 120.0 . . ? C21 C20 C19 114.4(3) . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C25 C26 C27 114.4(3) . . ? C25 C26 H26A 108.7 . . ? C27 C26 H26A 108.7 . . ? C25 C26 H26B 108.7 . . ? C27 C26 H26B 108.7 . . ? H26A C26 H26B 107.6 . . ? C61 C60 C59 112.8(4) . . ? C61 C60 H60A 109.0 . . ? C59 C60 H60A 109.0 . . ? C61 C60 H60B 109.0 . . ? C59 C60 H60B 109.0 . . ? H60A C60 H60B 107.8 . . ? C18 C17 C16 121.1(3) . . ? C18 C17 H17A 119.4 . . ? C16 C17 H17A 119.4 . . ? C38 C39 C40 121.0(3) . . ? C38 C39 H39A 119.5 . . ? C40 C39 H39A 119.5 . . ? C23 C22 C21 119.3(3) . . ? C23 C22 H22A 120.3 . . ? C21 C22 H22A 120.3 . . ? N3 C21 C22 121.6(4) . . ? N3 C21 C20 117.3(3) . . ? C22 C21 C20 121.1(3) . . ? C54 C53 C52 113.5(3) . . ? C54 C53 H53A 108.9 . . ? C52 C53 H53A 108.9 . . ? C54 C53 H53B 108.9 . . ? C52 C53 H53B 108.9 . . ? H53A C53 H53B 107.7 . . ? C28 C27 C26 113.4(3) . . ? C28 C27 H27A 108.9 . . ? C26 C27 H27A 108.9 . . ? C28 C27 H27B 108.9 . . ? C26 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? C33 C32 C31 118.5(4) . . ? C33 C32 H32A 120.7 . . ? C31 C32 H32A 120.7 . . ? C64 C63 C62 120.5(3) . . ? C64 C63 H63A 119.8 . . ? C62 C63 H63A 119.8 . . ? C43 C42 C40 120.7(3) . . ? C43 C42 H42A 119.7 . . ? C40 C42 H42A 119.7 . . ? C58 C59 C60 114.8(3) . . ? C58 C59 H59A 108.6 . . ? C60 C59 H59A 108.6 . . ? C58 C59 H59B 108.6 . . ? C60 C59 H59B 108.6 . . ? H59A C59 H59B 107.5 . . ? C23 C24 C25 117.5(4) . . ? C23 C24 H24A 121.2 . . ? C25 C24 H24A 121.2 . . ? C63 C62 C61 121.1(3) . . ? C63 C62 H62A 119.5 . . ? C61 C62 H62A 119.5 . . ? N6 C58 C57 121.9(4) . . ? N6 C58 C59 113.9(4) . . ? C57 C58 C59 124.3(4) . . ? C33 C28 C29 116.1(4) . . ? C33 C28 C27 125.0(3) . . ? C29 C28 C27 118.9(4) . . ? C57 C56 C55 118.4(4) . . ? C57 C56 H56A 120.8 . . ? C55 C56 H56A 120.8 . . ? C42 C43 C44 122.5(3) . . ? C42 C43 H43A 118.8 . . ? C44 C43 H43A 118.8 . . ? C58 C57 C56 120.0(4) . . ? C58 C57 H57A 120.0 . . ? C56 C57 H57A 120.0 . . ? C54 C55 C56 119.4(4) . . ? C54 C55 H55A 120.3 . . ? C56 C55 H55A 120.3 . . ? C30 C29 C28 121.1(4) . . ? C30 C29 H29A 119.4 . . ? C28 C29 H29A 119.4 . . ? C30 C31 C32 119.6(4) . . ? C30 C31 H31A 120.2 . . ? C32 C31 H31A 120.2 . . ? C31 C30 C29 121.1(4) . . ? C31 C30 H30A 119.5 . . ? C29 C30 H30A 119.5 . . ? O1 S1 O2 118.4(3) . . ? O1 S1 O3 115.4(4) . . ? O2 S1 O3 108.7(3) . . ? O1 S1 C67 105.3(2) . . ? O2 S1 C67 106.4(3) . . ? O3 S1 C67 100.5(3) . . ? F2 C67 F1 109.9(5) . . ? F2 C67 F3 106.2(5) . . ? F1 C67 F3 105.8(5) . . ? F2 C67 S1 112.6(4) . . ? F1 C67 S1 113.8(4) . . ? F3 C67 S1 108.0(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 N4 P2 N5 C35 2.0(2) . . . . ? N4 P2 N5 C46 -178.1(2) . . . . ? N5 P2 N4 C34 -2.1(2) . . . . ? N5 P2 N4 C66 177.0(3) . . . . ? N1 P1 N2 C2 -0.7(2) . . . . ? N1 P1 N2 C13 -179.2(2) . . . . ? C35 N5 C46 C47 114.1(3) . . . . ? P2 N5 C46 C47 -65.8(3) . . . . ? C35 N5 C46 C51 -65.9(4) . . . . ? P2 N5 C46 C51 114.2(3) . . . . ? N2 P1 N1 C1 -0.6(2) . . . . ? N2 P1 N1 C33 175.9(3) . . . . ? C2 N2 C13 C18 -70.2(4) . . . . ? P1 N2 C13 C18 108.2(3) . . . . ? C2 N2 C13 C14 111.7(3) . . . . ? P1 N2 C13 C14 -69.9(3) . . . . ? O5 S2 C68 F6 -178.2(2) . . . . ? O4 S2 C68 F6 59.5(3) . . . . ? O6 S2 C68 F6 -59.8(3) . . . . ? O5 S2 C68 F4 -56.3(3) . . . . ? O4 S2 C68 F4 -178.6(2) . . . . ? O6 S2 C68 F4 62.1(3) . . . . ? O5 S2 C68 F5 62.6(3) . . . . ? O4 S2 C68 F5 -59.7(2) . . . . ? O6 S2 C68 F5 -179.0(2) . . . . ? C49 C48 C47 C46 0.8(4) . . . . ? C51 C46 C47 C48 1.8(4) . . . . ? N5 C46 C47 C48 -178.2(3) . . . . ? C4 C3 C8 C7 -1.4(5) . . . . ? C2 C3 C8 C7 -179.9(3) . . . . ? C4 C3 C8 C12 178.1(3) . . . . ? C2 C3 C8 C12 -0.4(4) . . . . ? C38 C37 C36 C41 0.5(5) . . . . ? C38 C37 C36 C35 178.4(4) . . . . ? C47 C46 C51 C50 -2.8(4) . . . . ? N5 C46 C51 C50 177.2(3) . . . . ? C47 C46 C51 C52 173.7(3) . . . . ? N5 C46 C51 C52 -6.3(4) . . . . ? C18 C13 C14 C15 -1.4(4) . . . . ? N2 C13 C14 C15 176.5(2) . . . . ? C33 N1 C1 C2 -174.6(3) . . . . ? P1 N1 C1 C2 1.7(3) . . . . ? C33 N1 C1 C12 6.2(6) . . . . ? P1 N1 C1 C12 -177.4(3) . . . . ? C46 N5 C35 C34 178.8(3) . . . . ? P2 N5 C35 C34 -1.3(3) . . . . ? C46 N5 C35 C36 -0.2(6) . . . . ? P2 N5 C35 C36 179.7(3) . . . . ? C37 C36 C35 N5 1.0(7) . . . . ? C41 C36 C35 N5 179.0(4) . . . . ? C37 C36 C35 C34 -178.0(4) . . . . ? C41 C36 C35 C34 0.1(4) . . . . ? C34 N4 C66 C65 -105.9(3) . . . . ? P2 N4 C66 C65 75.0(4) . . . . ? C34 N4 C66 C61 71.0(4) . . . . ? P2 N4 C66 C61 -108.1(3) . . . . ? C13 N2 C2 C1 -179.7(3) . . . . ? P1 N2 C2 C1 1.8(3) . . . . ? C13 N2 C2 C3 -2.8(6) . . . . ? P1 N2 C2 C3 178.7(3) . . . . ? N1 C1 C2 N2 -2.2(4) . . . . ? C12 C1 C2 N2 177.2(3) . . . . ? N1 C1 C2 C3 180.0(3) . . . . ? C12 C1 C2 C3 -0.7(4) . . . . ? C4 C3 C2 N2 5.6(7) . . . . ? C8 C3 C2 N2 -176.3(4) . . . . ? C4 C3 C2 C1 -177.4(4) . . . . ? C8 C3 C2 C1 0.6(4) . . . . ? C1 N1 C33 C32 -119.1(3) . . . . ? P1 N1 C33 C32 64.8(4) . . . . ? C1 N1 C33 C28 62.6(4) . . . . ? P1 N1 C33 C28 -113.5(3) . . . . ? C47 C48 C49 C50 -2.3(5) . . . . ? C48 C49 C50 C51 1.3(5) . . . . ? C46 C51 C50 C49 1.2(5) . . . . ? C52 C51 C50 C49 -175.4(3) . . . . ? C10 C11 C12 C8 -0.9(5) . . . . ? C10 C11 C12 C1 178.4(4) . . . . ? C7 C8 C12 C11 -1.0(5) . . . . ? C3 C8 C12 C11 179.6(3) . . . . ? C7 C8 C12 C1 179.5(3) . . . . ? C3 C8 C12 C1 0.1(4) . . . . ? N1 C1 C12 C11 0.1(7) . . . . ? C2 C1 C12 C11 -179.0(4) . . . . ? N1 C1 C12 C8 179.5(4) . . . . ? C2 C1 C12 C8 0.4(4) . . . . ? C3 C8 C7 C6 1.1(5) . . . . ? C12 C8 C7 C6 -178.4(3) . . . . ? C3 C8 C7 C9 -178.6(3) . . . . ? C12 C8 C7 C9 2.0(5) . . . . ? C8 C7 C9 C10 -1.2(5) . . . . ? C6 C7 C9 C10 179.2(4) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C14 C13 C18 C17 1.6(4) . . . . ? N2 C13 C18 C17 -176.3(3) . . . . ? C14 C13 C18 C19 -178.4(3) . . . . ? N2 C13 C18 C19 3.6(4) . . . . ? C50 C51 C52 C53 81.6(4) . . . . ? C46 C51 C52 C53 -94.7(4) . . . . ? C66 N4 C34 C35 -177.4(3) . . . . ? P2 N4 C34 C35 1.8(4) . . . . ? C66 N4 C34 C45 1.1(6) . . . . ? P2 N4 C34 C45 -179.7(4) . . . . ? N5 C35 C34 N4 -0.3(4) . . . . ? C36 C35 C34 N4 179.0(3) . . . . ? N5 C35 C34 C45 -179.2(3) . . . . ? C36 C35 C34 C45 0.1(4) . . . . ? C8 C7 C6 C5 -0.4(5) . . . . ? C9 C7 C6 C5 179.2(3) . . . . ? C7 C6 C5 C4 0.0(6) . . . . ? C61 C66 C65 C64 -0.7(5) . . . . ? N4 C66 C65 C64 176.1(3) . . . . ? C37 C36 C41 C40 0.1(6) . . . . ? C35 C36 C41 C40 -178.5(4) . . . . ? C37 C36 C41 C45 178.3(3) . . . . ? C35 C36 C41 C45 -0.2(4) . . . . ? C36 C37 C38 C39 -0.7(5) . . . . ? C66 C65 C64 C63 0.0(5) . . . . ? C58 N6 C54 C55 -2.1(5) . . . . ? C58 N6 C54 C53 177.1(3) . . . . ? C7 C9 C10 C11 -0.6(5) . . . . ? C12 C11 C10 C9 1.7(5) . . . . ? C8 C3 C4 C5 0.9(5) . . . . ? C2 C3 C4 C5 178.7(4) . . . . ? C6 C5 C4 C3 -0.3(5) . . . . ? C36 C41 C40 C39 -0.5(6) . . . . ? C45 C41 C40 C39 -178.6(4) . . . . ? C36 C41 C40 C42 178.7(4) . . . . ? C45 C41 C40 C42 0.6(6) . . . . ? C40 C41 C45 C44 -0.7(6) . . . . ? C36 C41 C45 C44 -179.0(4) . . . . ? C40 C41 C45 C34 178.5(4) . . . . ? C36 C41 C45 C34 0.2(4) . . . . ? N4 C34 C45 C44 0.3(8) . . . . ? C35 C34 C45 C44 178.8(5) . . . . ? N4 C34 C45 C41 -178.7(4) . . . . ? C35 C34 C45 C41 -0.2(4) . . . . ? C41 C45 C44 C43 -0.2(6) . . . . ? C34 C45 C44 C43 -179.1(4) . . . . ? C65 C66 C61 C62 0.3(5) . . . . ? N4 C66 C61 C62 -176.5(3) . . . . ? C65 C66 C61 C60 -178.1(4) . . . . ? N4 C66 C61 C60 5.1(6) . . . . ? C13 C18 C19 C20 -100.6(4) . . . . ? C17 C18 C19 C20 79.4(4) . . . . ? C14 C15 C16 C17 1.5(5) . . . . ? C21 N3 C25 C24 3.4(5) . . . . ? C21 N3 C25 C26 -174.9(3) . . . . ? C18 C19 C20 C21 75.1(4) . . . . ? N3 C25 C26 C27 -75.5(4) . . . . ? C24 C25 C26 C27 106.2(4) . . . . ? C66 C61 C60 C59 94.5(5) . . . . ? C62 C61 C60 C59 -83.8(4) . . . . ? C13 C18 C17 C16 -0.2(4) . . . . ? C19 C18 C17 C16 179.8(3) . . . . ? C15 C16 C17 C18 -1.3(5) . . . . ? C37 C38 C39 C40 0.2(6) . . . . ? C41 C40 C39 C38 0.4(6) . . . . ? C42 C40 C39 C38 -178.7(4) . . . . ? C24 C23 C22 C21 1.3(5) . . . . ? C25 N3 C21 C22 -2.4(5) . . . . ? C25 N3 C21 C20 177.2(3) . . . . ? C23 C22 C21 N3 0.1(5) . . . . ? C23 C22 C21 C20 -179.6(3) . . . . ? C19 C20 C21 N3 71.4(4) . . . . ? C19 C20 C21 C22 -109.0(4) . . . . ? N6 C54 C53 C52 74.5(4) . . . . ? C55 C54 C53 C52 -106.2(4) . . . . ? C51 C52 C53 C54 74.9(4) . . . . ? C25 C26 C27 C28 -74.5(4) . . . . ? C28 C33 C32 C31 -2.5(5) . . . . ? N1 C33 C32 C31 179.2(3) . . . . ? C65 C64 C63 C62 1.2(6) . . . . ? C41 C40 C42 C43 0.4(6) . . . . ? C39 C40 C42 C43 179.5(4) . . . . ? C61 C60 C59 C58 -83.0(4) . . . . ? C22 C23 C24 C25 -0.4(5) . . . . ? N3 C25 C24 C23 -2.0(5) . . . . ? C26 C25 C24 C23 176.2(3) . . . . ? C64 C63 C62 C61 -1.7(6) . . . . ? C66 C61 C62 C63 0.9(6) . . . . ? C60 C61 C62 C63 179.4(4) . . . . ? C54 N6 C58 C57 1.4(5) . . . . ? C54 N6 C58 C59 -178.4(3) . . . . ? C60 C59 C58 N6 -67.3(4) . . . . ? C60 C59 C58 C57 112.9(5) . . . . ? C32 C33 C28 C29 3.5(5) . . . . ? N1 C33 C28 C29 -178.3(3) . . . . ? C32 C33 C28 C27 -174.0(3) . . . . ? N1 C33 C28 C27 4.2(5) . . . . ? C26 C27 C28 C33 95.6(4) . . . . ? C26 C27 C28 C29 -81.9(4) . . . . ? C40 C42 C43 C44 -1.3(7) . . . . ? C45 C44 C43 C42 1.2(7) . . . . ? N6 C58 C57 C56 -0.1(6) . . . . ? C59 C58 C57 C56 179.6(4) . . . . ? C55 C56 C57 C58 -0.5(5) . . . . ? N6 C54 C55 C56 1.6(5) . . . . ? C53 C54 C55 C56 -177.7(3) . . . . ? C57 C56 C55 C54 -0.2(5) . . . . ? C33 C28 C29 C30 -2.3(6) . . . . ? C27 C28 C29 C30 175.4(4) . . . . ? C33 C32 C31 C30 0.3(7) . . . . ? C32 C31 C30 C29 0.8(8) . . . . ? C28 C29 C30 C31 0.2(8) . . . . ? O1 S1 C67 F2 -179.5(5) . . . . ? O2 S1 C67 F2 -52.9(5) . . . . ? O3 S1 C67 F2 60.3(6) . . . . ? O1 S1 C67 F1 54.6(5) . . . . ? O2 S1 C67 F1 -178.9(3) . . . . ? O3 S1 C67 F1 -65.6(4) . . . . ? O1 S1 C67 F3 -62.6(5) . . . . ? O2 S1 C67 F3 64.0(5) . . . . ? O3 S1 C67 F3 177.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.903 _refine_diff_density_min -0.717 _refine_diff_density_rms 0.059 data_2BH3[OTf] _database_code_depnum_ccdc_archive 'CCDC 781900' #TrackingRef '- CompiledCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C73 H66 B2 Cl2 F6 N6 O7 P2 S2' _chemical_formula_weight 1471.90 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.260(3) _cell_length_b 14.962(3) _cell_length_c 19.811(4) _cell_angle_alpha 88.78(3) _cell_angle_beta 77.03(3) _cell_angle_gamma 83.08(3) _cell_volume 3515.5(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20415 _cell_measurement_theta_min 1.72 _cell_measurement_theta_max 25.06 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1524 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9475 _exptl_absorpt_correction_T_max 0.9707 _exptl_absorpt_process_details SAINT _exptl_special_details ; Dichloromethane solvate was disordered and modelled appropriately Since the chlorine atoms on the carbon of dichloromethane were disordered, hydrogen atoms could not be added ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _diffrn_measurement_method '\f scans, and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 43355 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.05 _diffrn_reflns_theta_max 25.06 _reflns_number_total 12379 _reflns_number_gt 8125 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2 _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0715P)^2^+3.5855P] 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_number_reflns 12379 _refine_ls_number_parameters 913 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1396 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.071 _refine_ls_shift/su_mean 0.002 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 P2 P 0.86900(8) 0.72051(6) 0.31836(5) 0.0235(2) Uani 1 1 d . . . P1 P 0.87809(8) 0.22795(7) 0.21701(5) 0.0239(2) Uani 1 1 d . . . S1 S 0.11899(8) 0.13624(7) 0.07459(5) 0.0324(2) Uani 1 1 d . . . S2 S 0.10378(8) 0.64788(7) 0.41541(5) 0.0349(3) Uani 1 1 d . . . O3 O 0.0628(2) 0.22651(19) 0.07973(14) 0.0384(7) Uani 1 1 d . . . F3 F 0.2979(2) 0.20741(19) 0.08601(13) 0.0551(7) Uani 1 1 d . . . O2 O 0.0961(2) 0.0810(2) 0.02268(14) 0.0433(7) Uani 1 1 d . . . N1 N 0.9341(2) 0.3252(2) 0.21572(14) 0.0219(7) Uani 1 1 d . . . F2 F 0.3342(2) 0.0769(2) 0.03761(15) 0.0625(8) Uani 1 1 d . . . N2 N 0.8093(2) 0.26760(19) 0.15618(14) 0.0215(7) Uani 1 1 d . . . N4 N 0.8068(2) 0.7676(2) 0.39575(14) 0.0236(7) Uani 1 1 d . . . N5 N 0.9368(2) 0.8113(2) 0.29597(14) 0.0243(7) Uani 1 1 d . . . F1 F 0.2820(2) 0.1932(2) -0.01894(12) 0.0572(7) Uani 1 1 d . . . N6 N 0.6441(3) 0.8618(2) 0.26930(16) 0.0301(8) Uani 1 1 d . . . O1 O 0.1197(3) 0.0929(2) 0.14133(14) 0.0487(8) Uani 1 1 d . . . N3 N 0.6488(2) 0.3535(2) 0.32873(14) 0.0274(7) Uani 1 1 d . . . C13 C 0.7362(3) 0.2145(2) 0.12912(17) 0.0217(8) Uani 1 1 d . . . C66 C 0.7298(3) 0.7193(3) 0.44594(18) 0.0257(8) Uani 1 1 d . . . C28 C 0.9802(3) 0.3950(3) 0.31662(18) 0.0285(9) Uani 1 1 d . . . C8 C 0.8684(3) 0.4865(2) 0.08681(17) 0.0255(8) Uani 1 1 d . . . C33 C 1.0128(3) 0.3369(2) 0.25925(17) 0.0246(8) Uani 1 1 d . . . C1 C 0.9037(3) 0.3851(2) 0.16839(17) 0.0233(8) Uani 1 1 d . . . C2 C 0.8324(3) 0.3510(2) 0.13361(17) 0.0232(8) Uani 1 1 d . . . C12 C 0.9288(3) 0.4735(2) 0.14074(18) 0.0259(8) Uani 1 1 d . . . C35 C 0.9147(3) 0.8751(2) 0.34724(18) 0.0253(8) Uani 1 1 d . . . C46 C 1.0136(3) 0.8162(3) 0.22871(18) 0.0257(8) Uani 1 1 d . . . C3 C 0.8070(3) 0.4138(3) 0.08025(18) 0.0257(8) Uani 1 1 d . . . C67 C 0.2651(3) 0.1541(3) 0.0432(2) 0.0377(10) Uani 1 1 d . . . C58 C 0.5881(3) 0.7978(3) 0.3073(2) 0.0353(10) Uani 1 1 d . . . C34 C 0.8397(3) 0.8492(2) 0.40489(18) 0.0250(8) Uani 1 1 d . . . C14 C 0.7878(3) 0.1408(2) 0.08767(17) 0.0242(8) Uani 1 1 d . . . H14A H 0.8675 0.1270 0.0770 0.029 Uiso 1 1 calc R . . C65 C 0.7749(3) 0.6408(3) 0.47322(18) 0.0283(9) Uani 1 1 d . . . H65A H 0.8539 0.6229 0.4618 0.034 Uiso 1 1 calc R . . C48 C 1.1879(3) 0.7598(3) 0.15326(19) 0.0354(10) Uani 1 1 d . . . H48A H 1.2569 0.7210 0.1447 0.042 Uiso 1 1 calc R . . C45 C 0.8216(3) 0.9180(3) 0.4593(2) 0.0320(9) Uani 1 1 d . . . C7 C 0.8732(3) 0.5608(3) 0.04334(19) 0.0303(9) Uani 1 1 d . . . C18 C 0.6201(3) 0.2378(3) 0.14642(18) 0.0257(8) Uani 1 1 d . . . C6 C 0.8112(3) 0.5616(3) -0.00909(19) 0.0350(10) Uani 1 1 d . . . H6A H 0.8114 0.6108 -0.0402 0.042 Uiso 1 1 calc R . . C15 C 0.7206(3) 0.0876(3) 0.06207(18) 0.0303(9) Uani 1 1 d . . . H15A H 0.7543 0.0371 0.0334 0.036 Uiso 1 1 calc R . . C49 C 1.1607(3) 0.8174(3) 0.1023(2) 0.0396(11) Uani 1 1 d . . . H49A H 1.2111 0.8178 0.0582 0.048 Uiso 1 1 calc R . . C36 C 0.9514(3) 0.9610(3) 0.3599(2) 0.0328(9) Uani 1 1 d . . . C11 C 0.9924(3) 0.5386(3) 0.15219(19) 0.0304(9) Uani 1 1 d . . . H11A H 1.0318 0.5328 0.1885 0.036 Uiso 1 1 calc R . . C21 C 0.6014(3) 0.2816(3) 0.31047(19) 0.0299(9) Uani 1 1 d . . . C4 C 0.7477(3) 0.4164(3) 0.02925(19) 0.0317(9) Uani 1 1 d . . . H4A H 0.7055 0.3689 0.0238 0.038 Uiso 1 1 calc R . . C54 C 0.7173(3) 0.8376(3) 0.2074(2) 0.0336(10) Uani 1 1 d . . . C47 C 1.1129(3) 0.7598(3) 0.21691(19) 0.0297(9) Uani 1 1 d . . . H47A H 1.1302 0.7207 0.2525 0.036 Uiso 1 1 calc R . . C31 C 1.1922(3) 0.2892(3) 0.2849(2) 0.0386(10) Uani 1 1 d . . . H31A H 1.2640 0.2543 0.2741 0.046 Uiso 1 1 calc R . . C24 C 0.7551(3) 0.2521(3) 0.39155(19) 0.0332(10) Uani 1 1 d . . . H24A H 0.8085 0.2426 0.4198 0.040 Uiso 1 1 calc R . . C25 C 0.7263(3) 0.3383(3) 0.36925(18) 0.0286(9) Uani 1 1 d . . . C61 C 0.6153(3) 0.7503(3) 0.46284(19) 0.0326(9) Uani 1 1 d . . . C41 C 0.8922(3) 0.9826(3) 0.4288(2) 0.0356(10) Uani 1 1 d . . . C19 C 0.5618(3) 0.3190(3) 0.1901(2) 0.0336(9) Uani 1 1 d . . . H19A H 0.4990 0.3472 0.1701 0.040 Uiso 1 1 calc R . . H19B H 0.6160 0.3635 0.1878 0.040 Uiso 1 1 calc R . . C9 C 0.9423(3) 0.6257(3) 0.0553(2) 0.0357(10) Uani 1 1 d . . . H9A H 0.9500 0.6771 0.0265 0.043 Uiso 1 1 calc R . . C32 C 1.1160(3) 0.2853(3) 0.24288(19) 0.0308(9) Uani 1 1 d . . . H32A H 1.1350 0.2473 0.2031 0.037 Uiso 1 1 calc R . . C10 C 0.9976(3) 0.6148(3) 0.1082(2) 0.0369(10) Uani 1 1 d . . . H10A H 1.0416 0.6602 0.1158 0.044 Uiso 1 1 calc R . . C51 C 0.9833(3) 0.8759(3) 0.1789(2) 0.0322(9) Uani 1 1 d . . . C64 C 0.7042(3) 0.5888(3) 0.51700(19) 0.0343(10) Uani 1 1 d . . . H64A H 0.7339 0.5345 0.5355 0.041 Uiso 1 1 calc R . . C50 C 1.0607(4) 0.8744(3) 0.1151(2) 0.0409(11) Uani 1 1 d . . . H50A H 1.0440 0.9136 0.0795 0.049 Uiso 1 1 calc R . . C29 C 1.0589(4) 0.3962(3) 0.3580(2) 0.0379(10) Uani 1 1 d . . . H29A H 1.0407 0.4339 0.3980 0.045 Uiso 1 1 calc R . . C26 C 0.7793(3) 0.4147(3) 0.39098(19) 0.0350(10) Uani 1 1 d . . . H26A H 0.8144 0.3942 0.4299 0.042 Uiso 1 1 calc R . . H26B H 0.7189 0.4641 0.4087 0.042 Uiso 1 1 calc R . . C22 C 0.6305(3) 0.1957(3) 0.3322(2) 0.0351(10) Uani 1 1 d . . . H22A H 0.5973 0.1468 0.3187 0.042 Uiso 1 1 calc R . . C17 C 0.5563(3) 0.1821(3) 0.1195(2) 0.0343(10) Uani 1 1 d . . . H17A H 0.4766 0.1956 0.1300 0.041 Uiso 1 1 calc R . . C23 C 0.7079(3) 0.1804(3) 0.3735(2) 0.0373(10) Uani 1 1 d . . . H23A H 0.7279 0.1215 0.3891 0.045 Uiso 1 1 calc R . . C60 C 0.5641(3) 0.8366(3) 0.4355(2) 0.0409(11) Uani 1 1 d . . . H60A H 0.6239 0.8760 0.4194 0.049 Uiso 1 1 calc R . . H60B H 0.5075 0.8682 0.4738 0.049 Uiso 1 1 calc R . . C5 C 0.7507(3) 0.4919(3) -0.01522(19) 0.0361(10) Uani 1 1 d . . . H5A H 0.7094 0.4943 -0.0506 0.043 Uiso 1 1 calc R . . C27 C 0.8691(4) 0.4529(3) 0.33437(19) 0.0352(10) Uani 1 1 d . . . H27A H 0.8394 0.4621 0.2919 0.042 Uiso 1 1 calc R . . H27B H 0.8816 0.5126 0.3498 0.042 Uiso 1 1 calc R . . C59 C 0.5071(3) 0.8217(3) 0.3755(2) 0.0481(12) Uani 1 1 d . . . H59A H 0.4587 0.7728 0.3883 0.058 Uiso 1 1 calc R . . H59B H 0.4576 0.8772 0.3694 0.058 Uiso 1 1 calc R . . C52 C 0.8766(3) 0.9396(3) 0.1911(2) 0.0396(10) Uani 1 1 d . . . H52A H 0.8937 0.9975 0.1686 0.048 Uiso 1 1 calc R . . H52B H 0.8509 0.9512 0.2416 0.048 Uiso 1 1 calc R . . C44 C 0.7583(4) 0.9315(3) 0.5254(2) 0.0413(11) Uani 1 1 d . . . H44A H 0.7092 0.8894 0.5467 0.050 Uiso 1 1 calc R . . C20 C 0.5147(3) 0.2969(3) 0.2670(2) 0.0385(10) Uani 1 1 d . . . H20A H 0.4576 0.3471 0.2877 0.046 Uiso 1 1 calc R . . H20B H 0.4759 0.2423 0.2690 0.046 Uiso 1 1 calc R . . C40 C 0.9042(4) 1.0608(3) 0.4632(3) 0.0466(12) Uani 1 1 d . . . C55 C 0.7310(4) 0.7507(3) 0.1835(2) 0.0439(11) Uani 1 1 d . . . H55A H 0.7800 0.7354 0.1399 0.053 Uiso 1 1 calc R . . C37 C 1.0215(4) 1.0192(3) 0.3234(3) 0.0432(11) Uani 1 1 d . . . H37A H 1.0594 1.0075 0.2765 0.052 Uiso 1 1 calc R . . C53 C 0.7790(3) 0.9072(3) 0.1645(2) 0.0410(11) Uani 1 1 d . . . H53A H 0.7239 0.9602 0.1610 0.049 Uiso 1 1 calc R . . H53B H 0.8095 0.8826 0.1172 0.049 Uiso 1 1 calc R . . C16 C 0.6050(3) 0.1081(3) 0.07832(19) 0.0339(10) Uani 1 1 d . . . H16A H 0.5590 0.0715 0.0612 0.041 Uiso 1 1 calc R . . C63 C 0.5900(4) 0.6166(3) 0.5337(2) 0.0400(11) Uani 1 1 d . . . H63A H 0.5406 0.5810 0.5634 0.048 Uiso 1 1 calc R . . C30 C 1.1619(4) 0.3442(3) 0.3423(2) 0.0437(11) Uani 1 1 d . . . H30A H 1.2131 0.3465 0.3716 0.052 Uiso 1 1 calc R . . C43 C 0.7681(4) 1.0107(4) 0.5612(3) 0.0538(14) Uani 1 1 d . . . H43A H 0.7245 1.0209 0.6071 0.065 Uiso 1 1 calc R . . C62 C 0.5470(3) 0.6958(3) 0.5074(2) 0.0423(11) Uani 1 1 d . . . H62A H 0.4681 0.7139 0.5201 0.051 Uiso 1 1 calc R . . C39 C 0.9796(4) 1.1178(3) 0.4254(3) 0.0558(14) Uani 1 1 d . . . H39A H 0.9919 1.1707 0.4468 0.067 Uiso 1 1 calc R . . C57 C 0.6030(4) 0.7103(3) 0.2841(3) 0.0470(12) Uani 1 1 d . . . H57A H 0.5632 0.6666 0.3115 0.056 Uiso 1 1 calc R . . C38 C 1.0348(4) 1.0982(3) 0.3589(3) 0.0564(14) Uani 1 1 d . . . H38A H 1.0842 1.1385 0.3350 0.068 Uiso 1 1 calc R . . C42 C 0.8382(4) 1.0727(3) 0.5319(3) 0.0569(15) Uani 1 1 d . . . H42A H 0.8428 1.1242 0.5579 0.068 Uiso 1 1 calc R . . C56 C 0.6752(4) 0.6850(3) 0.2214(3) 0.0531(14) Uani 1 1 d . . . H56A H 0.6858 0.6247 0.2050 0.064 Uiso 1 1 calc R . . F4 F 0.2730(2) 0.7253(2) 0.34272(14) 0.0676(9) Uani 1 1 d . . . F6 F 0.2862(2) 0.6917(2) 0.44615(13) 0.0646(8) Uani 1 1 d . . . F5 F 0.3164(2) 0.5890(2) 0.36830(15) 0.0682(8) Uani 1 1 d . . . O7 O 0.5900(2) 0.4156(2) 0.88273(15) 0.0460(8) Uani 1 1 d . . . O4 O 0.0988(2) 0.5804(2) 0.46697(14) 0.0465(8) Uani 1 1 d . . . O5 O 0.0813(3) 0.6192(2) 0.35156(16) 0.0554(9) Uani 1 1 d . . . C68 C 0.2512(4) 0.6643(3) 0.3921(2) 0.0382(10) Uani 1 1 d . . . O6 O 0.0502(3) 0.7354(2) 0.4363(2) 0.0838(13) Uani 1 1 d . . . C70 C 0.6006(4) 0.4399(3) 0.8124(2) 0.0514(12) Uani 1 1 d . . . H70B H 0.5311 0.4770 0.8061 0.062 Uiso 1 1 calc R . . H70A H 0.6126 0.3852 0.7831 0.062 Uiso 1 1 calc R . . C71 C 0.6998(4) 0.4925(3) 0.7922(2) 0.0516(12) Uani 1 1 d . . . H71C H 0.7087 0.5107 0.7437 0.077 Uiso 1 1 calc R . . H71A H 0.7682 0.4549 0.7981 0.077 Uiso 1 1 calc R . . H71B H 0.6873 0.5462 0.8217 0.077 Uiso 1 1 calc R . . C72 C 0.4954(4) 0.3706(4) 0.9066(2) 0.0527(13) Uani 1 1 d . . . H72A H 0.4984 0.3178 0.8766 0.063 Uiso 1 1 calc R . . H72B H 0.4259 0.4113 0.9055 0.063 Uiso 1 1 calc R . . C73 C 0.4949(4) 0.3400(4) 0.9810(3) 0.0652(15) Uani 1 1 d . . . H73A H 0.4314 0.3053 0.9978 0.098 Uiso 1 1 calc R . . H73C H 0.4873 0.3928 1.0108 0.098 Uiso 1 1 calc R . . H73B H 0.5657 0.3022 0.9819 0.098 Uiso 1 1 calc R . . B1 B 0.6124(5) 0.4556(4) 0.3052(3) 0.0442(13) Uani 1 1 d . . . H1A H 0.6208 0.4984 0.3399 0.066 Uiso 1 1 calc R . . H1B H 0.5336 0.4617 0.3011 0.066 Uiso 1 1 calc R . . H1C H 0.6608 0.4681 0.2603 0.066 Uiso 1 1 calc R . . B2 B 0.6216(5) 0.9668(4) 0.2963(3) 0.0530(14) Uani 1 1 d . . . H2A H 0.5450 0.9790 0.3248 0.080 Uiso 1 1 calc R . . H2B H 0.6303 1.0071 0.2562 0.080 Uiso 1 1 calc R . . H2C H 0.6761 0.9771 0.3238 0.080 Uiso 1 1 calc R . . Cl1 Cl 0.45437(19) 0.89461(14) 0.12445(14) 0.1302(8) Uani 1 1 d D A . C69 C 0.3399(9) 0.9552(5) 0.1830(4) 0.131(3) Uani 1 1 d . . . Cl2 Cl 0.3237(2) 0.8952(2) 0.25188(12) 0.0678(11) Uani 0.504(4) 1 d PD A 1 Cl3 Cl 0.3424(3) 1.0355(3) 0.23724(19) 0.1217(19) Uani 0.496(4) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P2 0.0266(5) 0.0237(5) 0.0197(5) 0.0002(4) -0.0037(4) -0.0039(4) P1 0.0275(5) 0.0255(5) 0.0208(5) -0.0001(4) -0.0087(4) -0.0051(4) S1 0.0279(5) 0.0350(6) 0.0344(6) -0.0063(5) -0.0060(4) -0.0044(4) S2 0.0313(5) 0.0316(6) 0.0433(6) -0.0016(5) -0.0119(5) -0.0024(4) O3 0.0369(16) 0.0370(17) 0.0361(16) -0.0016(13) -0.0032(12) 0.0065(13) F3 0.0449(15) 0.076(2) 0.0513(16) -0.0166(14) -0.0173(12) -0.0217(14) O2 0.0387(16) 0.0494(19) 0.0452(18) -0.0159(14) -0.0121(14) -0.0108(14) N1 0.0238(15) 0.0265(17) 0.0168(15) -0.0026(13) -0.0061(12) -0.0045(13) F2 0.0369(14) 0.069(2) 0.080(2) -0.0160(16) -0.0172(14) 0.0132(14) N2 0.0219(15) 0.0243(17) 0.0187(15) -0.0019(13) -0.0046(12) -0.0047(13) N4 0.0236(16) 0.0267(18) 0.0204(16) 0.0016(13) -0.0053(13) -0.0025(13) N5 0.0244(16) 0.0277(18) 0.0219(16) 0.0048(14) -0.0074(13) -0.0046(13) F1 0.0516(16) 0.087(2) 0.0331(14) 0.0076(14) -0.0032(12) -0.0239(15) N6 0.0294(17) 0.0317(19) 0.0312(19) 0.0024(15) -0.0133(15) 0.0003(15) O1 0.066(2) 0.0443(19) 0.0325(17) 0.0070(14) -0.0013(15) -0.0116(16) N3 0.0269(17) 0.0325(19) 0.0191(16) -0.0009(14) -0.0007(13) 0.0033(14) C13 0.0274(19) 0.023(2) 0.0173(18) 0.0037(15) -0.0090(15) -0.0066(16) C66 0.029(2) 0.030(2) 0.0177(19) -0.0040(16) -0.0035(15) -0.0056(17) C28 0.040(2) 0.025(2) 0.024(2) 0.0017(16) -0.0084(17) -0.0135(18) C8 0.028(2) 0.026(2) 0.0192(19) -0.0014(16) 0.0001(15) -0.0015(16) C33 0.030(2) 0.029(2) 0.0191(19) 0.0017(16) -0.0100(16) -0.0113(17) C1 0.0228(18) 0.027(2) 0.0185(19) -0.0023(16) -0.0018(15) -0.0019(16) C2 0.0254(19) 0.024(2) 0.0184(19) -0.0026(15) -0.0014(15) -0.0032(16) C12 0.0252(19) 0.027(2) 0.023(2) -0.0028(16) -0.0014(16) -0.0024(16) C35 0.029(2) 0.025(2) 0.026(2) 0.0017(17) -0.0147(16) -0.0022(16) C46 0.029(2) 0.028(2) 0.022(2) 0.0040(16) -0.0057(16) -0.0139(17) C3 0.0258(19) 0.029(2) 0.021(2) 0.0003(16) -0.0037(16) -0.0008(16) C67 0.035(2) 0.046(3) 0.036(2) -0.006(2) -0.0134(19) -0.006(2) C58 0.025(2) 0.038(3) 0.047(3) 0.007(2) -0.0168(19) -0.0063(18) C34 0.0267(19) 0.025(2) 0.025(2) -0.0014(16) -0.0113(16) 0.0008(16) C14 0.030(2) 0.026(2) 0.0182(19) 0.0024(16) -0.0073(15) -0.0038(16) C65 0.034(2) 0.032(2) 0.0195(19) -0.0041(17) -0.0067(16) -0.0020(18) C48 0.029(2) 0.048(3) 0.028(2) 0.0027(19) -0.0033(17) -0.0069(19) C45 0.033(2) 0.029(2) 0.037(2) -0.0062(18) -0.0188(19) 0.0050(18) C7 0.036(2) 0.024(2) 0.025(2) 0.0007(17) 0.0020(17) 0.0001(17) C18 0.026(2) 0.029(2) 0.024(2) 0.0003(16) -0.0093(16) -0.0034(16) C6 0.045(2) 0.032(2) 0.022(2) 0.0061(17) -0.0018(18) 0.005(2) C15 0.046(2) 0.026(2) 0.021(2) 0.0013(16) -0.0095(18) -0.0076(18) C49 0.037(2) 0.053(3) 0.028(2) 0.009(2) 0.0003(18) -0.017(2) C36 0.033(2) 0.024(2) 0.047(3) 0.0037(19) -0.023(2) -0.0021(17) C11 0.032(2) 0.030(2) 0.029(2) -0.0061(17) -0.0032(17) -0.0070(17) C21 0.025(2) 0.036(2) 0.025(2) -0.0041(17) 0.0015(16) -0.0004(17) C4 0.032(2) 0.037(2) 0.028(2) -0.0011(18) -0.0108(17) -0.0001(18) C54 0.033(2) 0.042(3) 0.028(2) 0.0017(19) -0.0158(18) 0.0051(19) C47 0.029(2) 0.037(2) 0.026(2) 0.0071(17) -0.0097(17) -0.0073(18) C31 0.032(2) 0.051(3) 0.037(2) 0.001(2) -0.0139(19) -0.010(2) C24 0.032(2) 0.037(3) 0.027(2) 0.0021(18) -0.0042(17) 0.0079(18) C25 0.029(2) 0.036(2) 0.0167(19) -0.0033(16) 0.0004(16) 0.0029(17) C61 0.033(2) 0.037(2) 0.025(2) -0.0005(18) -0.0028(17) 0.0017(18) C41 0.040(2) 0.028(2) 0.045(3) -0.0058(19) -0.028(2) 0.0052(19) C19 0.026(2) 0.039(3) 0.036(2) -0.0044(19) -0.0132(17) 0.0049(18) C9 0.040(2) 0.028(2) 0.033(2) 0.0031(18) 0.0030(19) -0.0017(19) C32 0.030(2) 0.040(2) 0.025(2) -0.0033(18) -0.0090(17) -0.0081(18) C10 0.039(2) 0.028(2) 0.041(3) -0.0031(19) 0.000(2) -0.0103(19) C51 0.034(2) 0.034(2) 0.032(2) 0.0086(18) -0.0119(18) -0.0092(18) C64 0.050(3) 0.030(2) 0.023(2) -0.0005(17) -0.0072(19) -0.006(2) C50 0.050(3) 0.046(3) 0.030(2) 0.018(2) -0.011(2) -0.020(2) C29 0.055(3) 0.043(3) 0.020(2) -0.0020(18) -0.0111(19) -0.023(2) C26 0.041(2) 0.039(3) 0.024(2) -0.0053(18) -0.0084(18) 0.0012(19) C22 0.035(2) 0.031(2) 0.036(2) -0.0059(19) 0.0005(19) -0.0031(18) C17 0.028(2) 0.047(3) 0.032(2) 0.004(2) -0.0131(18) -0.0111(19) C23 0.039(2) 0.032(2) 0.034(2) 0.0014(19) 0.0004(19) 0.0091(19) C60 0.030(2) 0.050(3) 0.036(2) 0.001(2) 0.0009(18) 0.0069(19) C5 0.044(2) 0.040(3) 0.024(2) 0.0009(18) -0.0101(18) 0.003(2) C27 0.057(3) 0.026(2) 0.023(2) -0.0049(17) -0.0092(19) -0.0065(19) C59 0.027(2) 0.066(3) 0.049(3) 0.016(2) -0.007(2) -0.001(2) C52 0.045(3) 0.035(3) 0.040(2) 0.016(2) -0.013(2) -0.006(2) C44 0.042(2) 0.045(3) 0.036(2) -0.016(2) -0.015(2) 0.014(2) C20 0.025(2) 0.052(3) 0.037(2) -0.009(2) -0.0045(18) 0.0002(19) C40 0.048(3) 0.031(3) 0.071(3) -0.011(2) -0.041(3) 0.009(2) C55 0.048(3) 0.051(3) 0.035(2) -0.009(2) -0.022(2) 0.011(2) C37 0.043(3) 0.032(3) 0.064(3) 0.012(2) -0.030(2) -0.010(2) C53 0.040(2) 0.054(3) 0.029(2) 0.015(2) -0.0124(19) 0.001(2) C16 0.043(2) 0.038(3) 0.029(2) 0.0043(19) -0.0168(19) -0.021(2) C63 0.050(3) 0.042(3) 0.025(2) 0.0015(19) 0.0046(19) -0.016(2) C30 0.043(3) 0.060(3) 0.038(3) 0.006(2) -0.022(2) -0.023(2) C43 0.060(3) 0.056(3) 0.048(3) -0.024(3) -0.031(3) 0.026(3) C62 0.031(2) 0.057(3) 0.032(2) 0.001(2) 0.0069(18) -0.005(2) C39 0.058(3) 0.025(3) 0.100(4) -0.003(3) -0.052(3) 0.000(2) C57 0.044(3) 0.047(3) 0.061(3) 0.015(2) -0.031(2) -0.015(2) C38 0.051(3) 0.030(3) 0.102(5) 0.016(3) -0.045(3) -0.010(2) C42 0.066(3) 0.042(3) 0.072(4) -0.027(3) -0.045(3) 0.022(3) C56 0.068(3) 0.032(3) 0.074(4) -0.008(3) -0.051(3) 0.004(2) F4 0.076(2) 0.083(2) 0.0577(18) 0.0358(16) -0.0282(15) -0.0458(17) F6 0.0521(16) 0.114(3) 0.0384(15) 0.0043(15) -0.0184(12) -0.0381(17) F5 0.0434(16) 0.077(2) 0.070(2) 0.0030(16) 0.0101(14) 0.0051(15) O7 0.0473(18) 0.052(2) 0.0395(18) 0.0014(14) -0.0083(14) -0.0118(15) O4 0.0417(17) 0.071(2) 0.0299(16) 0.0132(15) -0.0078(13) -0.0195(16) O5 0.071(2) 0.058(2) 0.055(2) 0.0176(16) -0.0395(17) -0.0306(18) C68 0.042(2) 0.048(3) 0.026(2) 0.008(2) -0.0092(19) -0.012(2) O6 0.049(2) 0.049(2) 0.151(4) -0.036(2) -0.020(2) 0.0069(17) C70 0.064(3) 0.051(3) 0.042(3) 0.003(2) -0.023(2) 0.001(2) C71 0.052(3) 0.061(3) 0.038(3) 0.015(2) -0.006(2) -0.004(2) C72 0.032(2) 0.071(4) 0.058(3) -0.003(3) -0.013(2) -0.011(2) C73 0.048(3) 0.087(4) 0.069(4) 0.029(3) -0.020(3) -0.035(3) B1 0.048(3) 0.043(3) 0.039(3) -0.003(2) -0.008(2) 0.003(2) B2 0.059(4) 0.040(3) 0.058(4) 0.001(3) -0.010(3) 0.000(3) Cl1 0.1100(16) 0.0842(14) 0.195(2) -0.0026(14) -0.0342(15) -0.0050(12) C69 0.227(10) 0.083(5) 0.072(5) -0.015(4) -0.038(6) 0.029(6) Cl2 0.079(2) 0.092(2) 0.0420(15) 0.0117(13) -0.0209(13) -0.0380(16) Cl3 0.118(3) 0.181(5) 0.085(3) 0.014(3) -0.029(2) -0.084(3) _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 P2 N5 1.678(3) . ? P2 N4 1.679(3) . ? P1 N2 1.680(3) . ? P1 N1 1.680(3) . ? S1 O2 1.429(3) . ? S1 O3 1.435(3) . ? S1 O1 1.462(3) . ? S1 C67 1.810(4) . ? S2 O4 1.418(3) . ? S2 O6 1.419(4) . ? S2 O5 1.438(3) . ? S2 C68 1.807(4) . ? F3 C67 1.333(5) . ? N1 C1 1.364(4) . ? N1 C33 1.458(4) . ? F2 C67 1.339(5) . ? N2 C2 1.357(4) . ? N2 C13 1.458(4) . ? N4 C34 1.359(5) . ? N4 C66 1.454(5) . ? N5 C35 1.368(5) . ? N5 C46 1.455(5) . ? F1 C67 1.335(5) . ? N6 C58 1.360(5) . ? N6 C54 1.374(5) . ? N6 B2 1.642(6) . ? N3 C25 1.371(5) . ? N3 C21 1.374(5) . ? N3 B1 1.627(6) . ? C13 C14 1.389(5) . ? C13 C18 1.390(5) . ? C66 C65 1.389(5) . ? C66 C61 1.392(5) . ? C28 C29 1.401(5) . ? C28 C33 1.401(5) . ? C28 C27 1.498(6) . ? C8 C7 1.391(5) . ? C8 C3 1.419(5) . ? C8 C12 1.428(5) . ? C33 C32 1.375(5) . ? C1 C2 1.377(5) . ? C1 C12 1.460(5) . ? C2 C3 1.460(5) . ? C12 C11 1.371(5) . ? C35 C34 1.377(5) . ? C35 C36 1.457(5) . ? C46 C47 1.372(5) . ? C46 C51 1.399(5) . ? C3 C4 1.368(5) . ? C58 C57 1.374(6) . ? C58 C59 1.508(6) . ? C34 C45 1.467(5) . ? C14 C15 1.390(5) . ? C14 H14A 0.9500 . ? C65 C64 1.380(5) . ? C65 H65A 0.9500 . ? C48 C47 1.384(5) . ? C48 C49 1.385(6) . ? C48 H48A 0.9500 . ? C45 C44 1.370(6) . ? C45 C41 1.410(6) . ? C7 C6 1.417(5) . ? C7 C9 1.419(6) . ? C18 C17 1.397(5) . ? C18 C19 1.515(5) . ? C6 C5 1.373(6) . ? C6 H6A 0.9500 . ? C15 C16 1.379(5) . ? C15 H15A 0.9500 . ? C49 C50 1.383(6) . ? C49 H49A 0.9500 . ? C36 C37 1.376(6) . ? C36 C41 1.420(6) . ? C11 C10 1.420(6) . ? C11 H11A 0.9500 . ? C21 C22 1.378(6) . ? C21 C20 1.506(5) . ? C4 C5 1.416(6) . ? C4 H4A 0.9500 . ? C54 C55 1.371(6) . ? C54 C53 1.497(6) . ? C47 H47A 0.9500 . ? C31 C30 1.373(6) . ? C31 C32 1.390(5) . ? C31 H31A 0.9500 . ? C24 C23 1.368(6) . ? C24 C25 1.385(5) . ? C24 H24A 0.9500 . ? C25 C26 1.497(5) . ? C61 C62 1.396(6) . ? C61 C60 1.511(6) . ? C41 C40 1.406(6) . ? C19 C20 1.546(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C9 C10 1.367(6) . ? C9 H9A 0.9500 . ? C32 H32A 0.9500 . ? C10 H10A 0.9500 . ? C51 C50 1.399(6) . ? C51 C52 1.497(6) . ? C64 C63 1.379(6) . ? C64 H64A 0.9500 . ? C50 H50A 0.9500 . ? C29 C30 1.377(6) . ? C29 H29A 0.9500 . ? C26 C27 1.539(6) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C22 C23 1.383(6) . ? C22 H22A 0.9500 . ? C17 C16 1.382(6) . ? C17 H17A 0.9500 . ? C23 H23A 0.9500 . ? C60 C59 1.540(6) . ? C60 H60A 0.9900 . ? C60 H60B 0.9900 . ? C5 H5A 0.9500 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C52 C53 1.542(6) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C44 C43 1.425(6) . ? C44 H44A 0.9500 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C40 C39 1.412(7) . ? C40 C42 1.421(7) . ? C55 C56 1.376(7) . ? C55 H55A 0.9500 . ? C37 C38 1.431(7) . ? C37 H37A 0.9500 . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C16 H16A 0.9500 . ? C63 C62 1.377(6) . ? C63 H63A 0.9500 . ? C30 H30A 0.9500 . ? C43 C42 1.372(7) . ? C43 H43A 0.9500 . ? C62 H62A 0.9500 . ? C39 C38 1.360(7) . ? C39 H39A 0.9500 . ? C57 C56 1.385(7) . ? C57 H57A 0.9500 . ? C38 H38A 0.9500 . ? C42 H42A 0.9500 . ? C56 H56A 0.9500 . ? F4 C68 1.330(5) . ? F6 C68 1.328(5) . ? F5 C68 1.330(5) . ? O7 C72 1.397(5) . ? O7 C70 1.413(5) . ? C70 C71 1.503(6) . ? C70 H70B 0.9900 . ? C70 H70A 0.9900 . ? C71 H71C 0.9800 . ? C71 H71A 0.9800 . ? C71 H71B 0.9800 . ? C72 C73 1.532(7) . ? C72 H72A 0.9900 . ? C72 H72B 0.9900 . ? C73 H73A 0.9800 . ? C73 H73C 0.9800 . ? C73 H73B 0.9800 . ? B1 H1A 0.9800 . ? B1 H1B 0.9800 . ? B1 H1C 0.9800 . ? B2 H2A 0.9800 . ? B2 H2B 0.9800 . ? B2 H2C 0.9800 . ? Cl1 C69 1.773(9) . ? C69 Cl2 1.606(8) . ? C69 Cl3 1.636(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 P2 N4 90.24(15) . . ? N2 P1 N1 90.06(14) . . ? O2 S1 O3 115.53(18) . . ? O2 S1 O1 115.50(19) . . ? O3 S1 O1 114.20(17) . . ? O2 S1 C67 104.31(18) . . ? O3 S1 C67 102.18(19) . . ? O1 S1 C67 102.55(19) . . ? O4 S2 O6 117.4(2) . . ? O4 S2 O5 114.12(19) . . ? O6 S2 O5 112.8(2) . . ? O4 S2 C68 103.89(18) . . ? O6 S2 C68 102.8(2) . . ? O5 S2 C68 103.55(19) . . ? C1 N1 C33 126.3(3) . . ? C1 N1 P1 113.4(2) . . ? C33 N1 P1 120.2(2) . . ? C2 N2 C13 124.4(3) . . ? C2 N2 P1 113.4(2) . . ? C13 N2 P1 122.2(2) . . ? C34 N4 C66 126.7(3) . . ? C34 N4 P2 113.3(2) . . ? C66 N4 P2 119.9(2) . . ? C35 N5 C46 125.8(3) . . ? C35 N5 P2 113.3(2) . . ? C46 N5 P2 120.9(2) . . ? C58 N6 C54 119.0(4) . . ? C58 N6 B2 120.3(4) . . ? C54 N6 B2 120.7(4) . . ? C25 N3 C21 118.6(3) . . ? C25 N3 B1 119.9(3) . . ? C21 N3 B1 121.5(3) . . ? C14 C13 C18 123.1(3) . . ? C14 C13 N2 117.1(3) . . ? C18 C13 N2 119.8(3) . . ? C65 C66 C61 122.6(3) . . ? C65 C66 N4 117.3(3) . . ? C61 C66 N4 120.1(3) . . ? C29 C28 C33 115.7(4) . . ? C29 C28 C27 120.7(3) . . ? C33 C28 C27 123.6(3) . . ? C7 C8 C3 123.5(3) . . ? C7 C8 C12 123.5(3) . . ? C3 C8 C12 113.0(3) . . ? C32 C33 C28 123.0(3) . . ? C32 C33 N1 116.8(3) . . ? C28 C33 N1 120.2(3) . . ? N1 C1 C2 111.3(3) . . ? N1 C1 C12 138.9(3) . . ? C2 C1 C12 109.7(3) . . ? N2 C2 C1 111.9(3) . . ? N2 C2 C3 137.9(3) . . ? C1 C2 C3 110.2(3) . . ? C11 C12 C8 118.8(3) . . ? C11 C12 C1 137.6(3) . . ? C8 C12 C1 103.6(3) . . ? N5 C35 C34 111.3(3) . . ? N5 C35 C36 138.3(3) . . ? C34 C35 C36 110.3(3) . . ? C47 C46 C51 123.0(3) . . ? C47 C46 N5 117.5(3) . . ? C51 C46 N5 119.6(3) . . ? C4 C3 C8 119.1(3) . . ? C4 C3 C2 137.3(4) . . ? C8 C3 C2 103.5(3) . . ? F3 C67 F1 107.3(3) . . ? F3 C67 F2 107.0(3) . . ? F1 C67 F2 107.7(3) . . ? F3 C67 S1 111.1(3) . . ? F1 C67 S1 111.5(3) . . ? F2 C67 S1 112.0(3) . . ? N6 C58 C57 120.9(4) . . ? N6 C58 C59 120.6(4) . . ? C57 C58 C59 118.5(4) . . ? N4 C34 C35 111.8(3) . . ? N4 C34 C45 138.8(3) . . ? C35 C34 C45 109.3(3) . . ? C13 C14 C15 118.7(3) . . ? C13 C14 H14A 120.6 . . ? C15 C14 H14A 120.6 . . ? C64 C65 C66 119.6(4) . . ? C64 C65 H65A 120.2 . . ? C66 C65 H65A 120.2 . . ? C47 C48 C49 118.8(4) . . ? C47 C48 H48A 120.6 . . ? C49 C48 H48A 120.6 . . ? C44 C45 C41 119.5(4) . . ? C44 C45 C34 137.0(4) . . ? C41 C45 C34 103.5(3) . . ? C8 C7 C6 116.2(4) . . ? C8 C7 C9 116.2(4) . . ? C6 C7 C9 127.6(4) . . ? C13 C18 C17 116.0(3) . . ? C13 C18 C19 124.1(3) . . ? C17 C18 C19 119.8(3) . . ? C5 C6 C7 120.5(4) . . ? C5 C6 H6A 119.8 . . ? C7 C6 H6A 119.8 . . ? C16 C15 C14 120.0(4) . . ? C16 C15 H15A 120.0 . . ? C14 C15 H15A 120.0 . . ? C50 C49 C48 120.5(4) . . ? C50 C49 H49A 119.8 . . ? C48 C49 H49A 119.8 . . ? C37 C36 C41 119.8(4) . . ? C37 C36 C35 137.0(4) . . ? C41 C36 C35 103.2(3) . . ? C12 C11 C10 118.1(4) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? N3 C21 C22 121.1(3) . . ? N3 C21 C20 119.6(3) . . ? C22 C21 C20 119.3(4) . . ? C3 C4 C5 118.3(4) . . ? C3 C4 H4A 120.8 . . ? C5 C4 H4A 120.8 . . ? C55 C54 N6 120.3(4) . . ? C55 C54 C53 119.9(4) . . ? N6 C54 C53 119.8(4) . . ? C46 C47 C48 120.0(3) . . ? C46 C47 H47A 120.0 . . ? C48 C47 H47A 120.0 . . ? C30 C31 C32 118.9(4) . . ? C30 C31 H31A 120.6 . . ? C32 C31 H31A 120.6 . . ? C23 C24 C25 121.1(4) . . ? C23 C24 H24A 119.5 . . ? C25 C24 H24A 119.5 . . ? N3 C25 C24 120.4(4) . . ? N3 C25 C26 120.5(3) . . ? C24 C25 C26 119.1(3) . . ? C66 C61 C62 115.8(4) . . ? C66 C61 C60 123.9(4) . . ? C62 C61 C60 120.3(4) . . ? C40 C41 C45 123.6(4) . . ? C40 C41 C36 122.7(4) . . ? C45 C41 C36 113.7(4) . . ? C18 C19 C20 114.0(3) . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19B 108.8 . . ? C20 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C10 C9 C7 120.5(4) . . ? C10 C9 H9A 119.8 . . ? C7 C9 H9A 119.7 . . ? C33 C32 C31 119.6(4) . . ? C33 C32 H32A 120.2 . . ? C31 C32 H32A 120.2 . . ? C9 C10 C11 122.8(4) . . ? C9 C10 H10A 118.6 . . ? C11 C10 H10A 118.6 . . ? C50 C51 C46 115.7(4) . . ? C50 C51 C52 120.4(3) . . ? C46 C51 C52 123.9(3) . . ? C63 C64 C65 119.2(4) . . ? C63 C64 H64A 120.4 . . ? C65 C64 H64A 120.4 . . ? C49 C50 C51 122.0(4) . . ? C49 C50 H50A 119.0 . . ? C51 C50 H50A 119.0 . . ? C30 C29 C28 121.6(4) . . ? C30 C29 H29A 119.2 . . ? C28 C29 H29A 119.2 . . ? C25 C26 C27 115.8(3) . . ? C25 C26 H26A 108.3 . . ? C27 C26 H26A 108.3 . . ? C25 C26 H26B 108.3 . . ? C27 C26 H26B 108.3 . . ? H26A C26 H26B 107.4 . . ? C21 C22 C23 120.3(4) . . ? C21 C22 H22A 119.8 . . ? C23 C22 H22A 119.8 . . ? C16 C17 C18 122.4(4) . . ? C16 C17 H17A 118.8 . . ? C18 C17 H17A 118.8 . . ? C24 C23 C22 118.5(4) . . ? C24 C23 H23A 120.8 . . ? C22 C23 H23A 120.8 . . ? C61 C60 C59 113.4(4) . . ? C61 C60 H60A 108.9 . . ? C59 C60 H60A 108.9 . . ? C61 C60 H60B 108.9 . . ? C59 C60 H60B 108.9 . . ? H60A C60 H60B 107.7 . . ? C6 C5 C4 122.4(4) . . ? C6 C5 H5A 118.8 . . ? C4 C5 H5A 118.8 . . ? C28 C27 C26 114.7(3) . . ? C28 C27 H27A 108.6 . . ? C26 C27 H27A 108.6 . . ? C28 C27 H27B 108.6 . . ? C26 C27 H27B 108.6 . . ? H27A C27 H27B 107.6 . . ? C58 C59 C60 114.3(3) . . ? C58 C59 H59A 108.7 . . ? C60 C59 H59A 108.7 . . ? C58 C59 H59B 108.7 . . ? C60 C59 H59B 108.7 . . ? H59A C59 H59B 107.6 . . ? C51 C52 C53 115.4(4) . . ? C51 C52 H52A 108.4 . . ? C53 C52 H52A 108.4 . . ? C51 C52 H52B 108.4 . . ? C53 C52 H52B 108.4 . . ? H52A C52 H52B 107.5 . . ? C45 C44 C43 118.0(5) . . ? C45 C44 H44A 121.0 . . ? C43 C44 H44A 121.0 . . ? C21 C20 C19 115.0(3) . . ? C21 C20 H20A 108.5 . . ? C19 C20 H20A 108.5 . . ? C21 C20 H20B 108.5 . . ? C19 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? C41 C40 C39 116.2(5) . . ? C41 C40 C42 115.6(5) . . ? C39 C40 C42 128.2(5) . . ? C54 C55 C56 121.5(4) . . ? C54 C55 H55A 119.3 . . ? C56 C55 H55A 119.3 . . ? C36 C37 C38 117.3(5) . . ? C36 C37 H37A 121.3 . . ? C38 C37 H37A 121.3 . . ? C54 C53 C52 116.2(3) . . ? C54 C53 H53A 108.2 . . ? C52 C53 H53A 108.2 . . ? C54 C53 H53B 108.2 . . ? C52 C53 H53B 108.2 . . ? H53A C53 H53B 107.4 . . ? C15 C16 C17 119.9(4) . . ? C15 C16 H16A 120.1 . . ? C17 C16 H16A 120.1 . . ? C62 C63 C64 120.4(4) . . ? C62 C63 H63A 119.8 . . ? C64 C63 H63A 119.8 . . ? C31 C30 C29 121.3(4) . . ? C31 C30 H30A 119.4 . . ? C29 C30 H30A 119.4 . . ? C42 C43 C44 122.4(5) . . ? C42 C43 H43A 118.8 . . ? C44 C43 H43A 118.8 . . ? C63 C62 C61 122.3(4) . . ? C63 C62 H62A 118.8 . . ? C61 C62 H62A 118.8 . . ? C38 C39 C40 121.2(5) . . ? C38 C39 H39A 119.4 . . ? C40 C39 H39A 119.4 . . ? C58 C57 C56 120.8(4) . . ? C58 C57 H57A 119.6 . . ? C56 C57 H57A 119.6 . . ? C39 C38 C37 122.6(5) . . ? C39 C38 H38A 118.7 . . ? C37 C38 H38A 118.7 . . ? C43 C42 C40 120.8(4) . . ? C43 C42 H42A 119.6 . . ? C40 C42 H42A 119.6 . . ? C55 C56 C57 117.5(4) . . ? C55 C56 H56A 121.2 . . ? C57 C56 H56A 121.3 . . ? C72 O7 C70 111.3(3) . . ? F6 C68 F4 107.0(4) . . ? F6 C68 F5 107.3(4) . . ? F4 C68 F5 106.1(3) . . ? F6 C68 S2 111.4(3) . . ? F4 C68 S2 112.7(3) . . ? F5 C68 S2 112.0(3) . . ? O7 C70 C71 107.8(4) . . ? O7 C70 H70B 110.1 . . ? C71 C70 H70B 110.2 . . ? O7 C70 H70A 110.2 . . ? C71 C70 H70A 110.2 . . ? H70B C70 H70A 108.5 . . ? C70 C71 H71C 109.5 . . ? C70 C71 H71A 109.5 . . ? H71C C71 H71A 109.5 . . ? C70 C71 H71B 109.5 . . ? H71C C71 H71B 109.5 . . ? H71A C71 H71B 109.5 . . ? O7 C72 C73 108.2(4) . . ? O7 C72 H72A 110.1 . . ? C73 C72 H72A 110.1 . . ? O7 C72 H72B 110.1 . . ? C73 C72 H72B 110.1 . . ? H72A C72 H72B 108.4 . . ? C72 C73 H73A 109.5 . . ? C72 C73 H73C 109.5 . . ? H73A C73 H73C 109.5 . . ? C72 C73 H73B 109.5 . . ? H73A C73 H73B 109.5 . . ? H73C C73 H73B 109.5 . . ? N3 B1 H1A 109.5 . . ? N3 B1 H1B 109.5 . . ? H1A B1 H1B 109.5 . . ? N3 B1 H1C 109.5 . . ? H1A B1 H1C 109.5 . . ? H1B B1 H1C 109.5 . . ? N6 B2 H2A 109.5 . . ? N6 B2 H2B 109.5 . . ? H2A B2 H2B 109.5 . . ? N6 B2 H2C 109.5 . . ? H2A B2 H2C 109.5 . . ? H2B B2 H2C 109.5 . . ? Cl2 C69 Cl3 82.8(4) . . ? Cl2 C69 Cl1 104.3(4) . . ? Cl3 C69 Cl1 128.7(7) . . ? 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 N2 P1 N1 C1 -1.9(3) . . . . ? N2 P1 N1 C33 -178.2(3) . . . . ? N1 P1 N2 C2 2.6(2) . . . . ? N1 P1 N2 C13 -179.9(3) . . . . ? N5 P2 N4 C34 -1.8(2) . . . . ? N5 P2 N4 C66 -179.6(3) . . . . ? N4 P2 N5 C35 1.6(3) . . . . ? N4 P2 N5 C46 179.6(3) . . . . ? C2 N2 C13 C14 107.4(4) . . . . ? P1 N2 C13 C14 -69.8(4) . . . . ? C2 N2 C13 C18 -73.9(4) . . . . ? P1 N2 C13 C18 108.9(3) . . . . ? C34 N4 C66 C65 -111.5(4) . . . . ? P2 N4 C66 C65 66.0(4) . . . . ? C34 N4 C66 C61 71.0(5) . . . . ? P2 N4 C66 C61 -111.5(3) . . . . ? C29 C28 C33 C32 -1.5(5) . . . . ? C27 C28 C33 C32 178.8(4) . . . . ? C29 C28 C33 N1 175.4(3) . . . . ? C27 C28 C33 N1 -4.4(5) . . . . ? C1 N1 C33 C32 -108.0(4) . . . . ? P1 N1 C33 C32 67.7(4) . . . . ? C1 N1 C33 C28 75.0(5) . . . . ? P1 N1 C33 C28 -109.3(3) . . . . ? C33 N1 C1 C2 176.8(3) . . . . ? P1 N1 C1 C2 0.9(4) . . . . ? C33 N1 C1 C12 0.9(7) . . . . ? P1 N1 C1 C12 -175.0(4) . . . . ? C13 N2 C2 C1 180.0(3) . . . . ? P1 N2 C2 C1 -2.6(4) . . . . ? C13 N2 C2 C3 -3.7(6) . . . . ? P1 N2 C2 C3 173.8(4) . . . . ? N1 C1 C2 N2 1.1(4) . . . . ? C12 C1 C2 N2 178.2(3) . . . . ? N1 C1 C2 C3 -176.3(3) . . . . ? C12 C1 C2 C3 0.8(4) . . . . ? C7 C8 C12 C11 2.1(5) . . . . ? C3 C8 C12 C11 179.5(3) . . . . ? C7 C8 C12 C1 -176.4(3) . . . . ? C3 C8 C12 C1 1.1(4) . . . . ? N1 C1 C12 C11 -3.2(8) . . . . ? C2 C1 C12 C11 -179.1(4) . . . . ? N1 C1 C12 C8 174.8(4) . . . . ? C2 C1 C12 C8 -1.1(4) . . . . ? C46 N5 C35 C34 -178.9(3) . . . . ? P2 N5 C35 C34 -1.1(4) . . . . ? C46 N5 C35 C36 -2.5(6) . . . . ? P2 N5 C35 C36 175.3(4) . . . . ? C35 N5 C46 C47 108.5(4) . . . . ? P2 N5 C46 C47 -69.1(4) . . . . ? C35 N5 C46 C51 -72.6(5) . . . . ? P2 N5 C46 C51 109.8(3) . . . . ? C7 C8 C3 C4 -0.8(5) . . . . ? C12 C8 C3 C4 -178.3(3) . . . . ? C7 C8 C3 C2 176.8(3) . . . . ? C12 C8 C3 C2 -0.6(4) . . . . ? N2 C2 C3 C4 0.4(8) . . . . ? C1 C2 C3 C4 176.8(4) . . . . ? N2 C2 C3 C8 -176.5(4) . . . . ? C1 C2 C3 C8 -0.1(4) . . . . ? O2 S1 C67 F3 178.3(3) . . . . ? O3 S1 C67 F3 57.6(3) . . . . ? O1 S1 C67 F3 -60.9(3) . . . . ? O2 S1 C67 F1 58.6(3) . . . . ? O3 S1 C67 F1 -62.0(3) . . . . ? O1 S1 C67 F1 179.4(3) . . . . ? O2 S1 C67 F2 -62.2(3) . . . . ? O3 S1 C67 F2 177.1(3) . . . . ? O1 S1 C67 F2 58.6(3) . . . . ? C54 N6 C58 C57 -0.8(5) . . . . ? B2 N6 C58 C57 177.6(4) . . . . ? C54 N6 C58 C59 -180.0(3) . . . . ? B2 N6 C58 C59 -1.7(5) . . . . ? C66 N4 C34 C35 179.1(3) . . . . ? P2 N4 C34 C35 1.5(4) . . . . ? C66 N4 C34 C45 1.6(6) . . . . ? P2 N4 C34 C45 -176.0(4) . . . . ? N5 C35 C34 N4 -0.2(4) . . . . ? C36 C35 C34 N4 -177.7(3) . . . . ? N5 C35 C34 C45 178.0(3) . . . . ? C36 C35 C34 C45 0.5(4) . . . . ? C18 C13 C14 C15 0.1(5) . . . . ? N2 C13 C14 C15 178.8(3) . . . . ? C61 C66 C65 C64 2.3(6) . . . . ? N4 C66 C65 C64 -175.1(3) . . . . ? N4 C34 C45 C44 -3.5(8) . . . . ? C35 C34 C45 C44 178.9(4) . . . . ? N4 C34 C45 C41 176.7(4) . . . . ? C35 C34 C45 C41 -0.8(4) . . . . ? C3 C8 C7 C6 0.7(5) . . . . ? C12 C8 C7 C6 177.8(3) . . . . ? C3 C8 C7 C9 -177.5(3) . . . . ? C12 C8 C7 C9 -0.4(5) . . . . ? C14 C13 C18 C17 0.0(5) . . . . ? N2 C13 C18 C17 -178.6(3) . . . . ? C14 C13 C18 C19 -178.6(3) . . . . ? N2 C13 C18 C19 2.8(5) . . . . ? C8 C7 C6 C5 0.0(5) . . . . ? C9 C7 C6 C5 177.9(4) . . . . ? C13 C14 C15 C16 -0.4(5) . . . . ? C47 C48 C49 C50 0.5(6) . . . . ? N5 C35 C36 C37 4.6(8) . . . . ? C34 C35 C36 C37 -178.9(4) . . . . ? N5 C35 C36 C41 -176.5(4) . . . . ? C34 C35 C36 C41 0.0(4) . . . . ? C8 C12 C11 C10 -1.9(5) . . . . ? C1 C12 C11 C10 175.9(4) . . . . ? C25 N3 C21 C22 0.0(5) . . . . ? B1 N3 C21 C22 -178.3(4) . . . . ? C25 N3 C21 C20 179.0(3) . . . . ? B1 N3 C21 C20 0.7(5) . . . . ? C8 C3 C4 C5 0.3(5) . . . . ? C2 C3 C4 C5 -176.3(4) . . . . ? C58 N6 C54 C55 1.8(5) . . . . ? B2 N6 C54 C55 -176.5(4) . . . . ? C58 N6 C54 C53 179.5(3) . . . . ? B2 N6 C54 C53 1.2(5) . . . . ? C51 C46 C47 C48 -0.5(6) . . . . ? N5 C46 C47 C48 178.3(3) . . . . ? C49 C48 C47 C46 0.0(6) . . . . ? C21 N3 C25 C24 -0.5(5) . . . . ? B1 N3 C25 C24 177.8(3) . . . . ? C21 N3 C25 C26 -179.4(3) . . . . ? B1 N3 C25 C26 -1.1(5) . . . . ? C23 C24 C25 N3 0.4(5) . . . . ? C23 C24 C25 C26 179.4(3) . . . . ? C65 C66 C61 C62 -2.1(6) . . . . ? N4 C66 C61 C62 175.3(3) . . . . ? C65 C66 C61 C60 178.4(4) . . . . ? N4 C66 C61 C60 -4.2(6) . . . . ? C44 C45 C41 C40 1.7(6) . . . . ? C34 C45 C41 C40 -178.5(3) . . . . ? C44 C45 C41 C36 -179.0(3) . . . . ? C34 C45 C41 C36 0.8(4) . . . . ? C37 C36 C41 C40 -2.1(6) . . . . ? C35 C36 C41 C40 178.8(3) . . . . ? C37 C36 C41 C45 178.6(3) . . . . ? C35 C36 C41 C45 -0.5(4) . . . . ? C13 C18 C19 C20 -98.8(4) . . . . ? C17 C18 C19 C20 82.6(4) . . . . ? C8 C7 C9 C10 -1.5(5) . . . . ? C6 C7 C9 C10 -179.5(4) . . . . ? C28 C33 C32 C31 0.8(6) . . . . ? N1 C33 C32 C31 -176.1(3) . . . . ? C30 C31 C32 C33 0.5(6) . . . . ? C7 C9 C10 C11 1.8(6) . . . . ? C12 C11 C10 C9 0.0(6) . . . . ? C47 C46 C51 C50 0.6(6) . . . . ? N5 C46 C51 C50 -178.3(3) . . . . ? C47 C46 C51 C52 -178.5(4) . . . . ? N5 C46 C51 C52 2.6(6) . . . . ? C66 C65 C64 C63 -0.9(6) . . . . ? C48 C49 C50 C51 -0.4(7) . . . . ? C46 C51 C50 C49 -0.1(6) . . . . ? C52 C51 C50 C49 179.1(4) . . . . ? C33 C28 C29 C30 0.9(6) . . . . ? C27 C28 C29 C30 -179.4(4) . . . . ? N3 C25 C26 C27 -74.3(4) . . . . ? C24 C25 C26 C27 106.7(4) . . . . ? N3 C21 C22 C23 0.5(6) . . . . ? C20 C21 C22 C23 -178.5(3) . . . . ? C13 C18 C17 C16 0.2(5) . . . . ? C19 C18 C17 C16 178.8(3) . . . . ? C25 C24 C23 C22 0.1(6) . . . . ? C21 C22 C23 C24 -0.6(6) . . . . ? C66 C61 C60 C59 101.0(5) . . . . ? C62 C61 C60 C59 -78.5(5) . . . . ? C7 C6 C5 C4 -0.5(6) . . . . ? C3 C4 C5 C6 0.3(6) . . . . ? C29 C28 C27 C26 -80.7(5) . . . . ? C33 C28 C27 C26 99.0(4) . . . . ? C25 C26 C27 C28 -74.8(4) . . . . ? N6 C58 C59 C60 -75.1(5) . . . . ? C57 C58 C59 C60 105.7(5) . . . . ? C61 C60 C59 C58 -74.5(5) . . . . ? C50 C51 C52 C53 83.2(5) . . . . ? C46 C51 C52 C53 -97.7(5) . . . . ? C41 C45 C44 C43 -1.0(6) . . . . ? C34 C45 C44 C43 179.2(4) . . . . ? N3 C21 C20 C19 72.7(5) . . . . ? C22 C21 C20 C19 -108.3(4) . . . . ? C18 C19 C20 C21 77.1(4) . . . . ? C45 C41 C40 C39 179.1(4) . . . . ? C36 C41 C40 C39 -0.1(6) . . . . ? C45 C41 C40 C42 -1.1(6) . . . . ? C36 C41 C40 C42 179.6(4) . . . . ? N6 C54 C55 C56 -2.0(6) . . . . ? C53 C54 C55 C56 -179.7(4) . . . . ? C41 C36 C37 C38 2.8(6) . . . . ? C35 C36 C37 C38 -178.4(4) . . . . ? C55 C54 C53 C52 -108.3(4) . . . . ? N6 C54 C53 C52 74.1(5) . . . . ? C51 C52 C53 C54 76.5(5) . . . . ? C14 C15 C16 C17 0.6(5) . . . . ? C18 C17 C16 C15 -0.5(6) . . . . ? C65 C64 C63 C62 -0.6(6) . . . . ? C32 C31 C30 C29 -1.0(6) . . . . ? C28 C29 C30 C31 0.3(6) . . . . ? C45 C44 C43 C42 -0.1(6) . . . . ? C64 C63 C62 C61 0.8(7) . . . . ? C66 C61 C62 C63 0.5(6) . . . . ? C60 C61 C62 C63 -179.9(4) . . . . ? C41 C40 C39 C38 1.4(6) . . . . ? C42 C40 C39 C38 -178.3(4) . . . . ? N6 C58 C57 C56 -0.1(6) . . . . ? C59 C58 C57 C56 179.1(4) . . . . ? C40 C39 C38 C37 -0.6(7) . . . . ? C36 C37 C38 C39 -1.6(6) . . . . ? C44 C43 C42 C40 0.7(7) . . . . ? C41 C40 C42 C43 -0.1(6) . . . . ? C39 C40 C42 C43 179.6(4) . . . . ? C54 C55 C56 C57 1.1(6) . . . . ? C58 C57 C56 C55 0.0(6) . . . . ? O4 S2 C68 F6 -60.8(4) . . . . ? O6 S2 C68 F6 62.1(4) . . . . ? O5 S2 C68 F6 179.7(3) . . . . ? O4 S2 C68 F4 179.0(3) . . . . ? O6 S2 C68 F4 -58.1(4) . . . . ? O5 S2 C68 F4 59.5(4) . . . . ? O4 S2 C68 F5 59.5(3) . . . . ? O6 S2 C68 F5 -177.7(3) . . . . ? O5 S2 C68 F5 -60.1(3) . . . . ? C72 O7 C70 C71 176.7(4) . . . . ? C70 O7 C72 C73 175.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.789 _refine_diff_density_min -1.141 _refine_diff_density_rms 0.063 data_2DMAP[OTf] _database_code_depnum_ccdc_archive 'CCDC 781901' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H35 Cl2 F3 N5 O3 P S' _chemical_formula_weight 848.68 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 10.5053(5) _cell_length_b 17.6658(8) _cell_length_c 22.5701(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4188.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 121998 _cell_measurement_theta_min 1.46 _cell_measurement_theta_max 26.05 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9422 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details SAINT _exptl_special_details ; Dichloromethane solvate was disordered and modelled appropriately Since the chlorine atoms on the carbon of dichloromethane were disordered, hydrogen atoms could not be added ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _diffrn_measurement_method '\f scans, and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 121998 _diffrn_reflns_av_R_equivalents 0.1105 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 26.05 _reflns_number_total 8260 _reflns_number_gt 6058 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2 _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.1180P)^2^+2.6686P] 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' _refine_ls_abs_structure_Flack 0.00(12) _refine_ls_number_reflns 8260 _refine_ls_number_parameters 524 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1015 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.1986 _refine_ls_wR_factor_gt 0.1756 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.40298(11) 0.02173(6) 0.06025(5) 0.0203(3) Uani 1 1 d . . . S1 S 0.44356(14) 0.73775(8) 0.89193(7) 0.0437(4) Uani 1 1 d . . . N4 N 0.4029(4) -0.08324(18) 0.05937(17) 0.0221(8) Uani 1 1 d . . . C12 C 0.0928(5) 0.0587(2) -0.0397(2) 0.0218(9) Uani 1 1 d . . . N2 N 0.2629(4) 0.0367(2) 0.09638(16) 0.0220(8) Uani 1 1 d . . . C4 C -0.0703(5) 0.0372(2) 0.1014(2) 0.0301(11) Uani 1 1 d . . . H4A H -0.0490 0.0302 0.1419 0.036 Uiso 1 1 calc R . . C3 C 0.0220(4) 0.0451(2) 0.0589(2) 0.0239(10) Uani 1 1 d . . . C7 C -0.1406(5) 0.0593(2) -0.0200(2) 0.0271(11) Uani 1 1 d . . . N3 N 0.3453(4) 0.2375(2) 0.05609(18) 0.0252(8) Uani 1 1 d . . . C8 C -0.0147(4) 0.0544(2) -0.0008(2) 0.0225(10) Uani 1 1 d . . . C2 C 0.1612(4) 0.0453(2) 0.0567(2) 0.0208(9) Uani 1 1 d . . . C33 C 0.4013(4) 0.0477(2) -0.0613(2) 0.0208(9) Uani 1 1 d . . . N1 N 0.3341(4) 0.0447(2) -0.00532(16) 0.0197(8) Uani 1 1 d . . . C21 C 0.3619(5) 0.2254(2) 0.1141(2) 0.0265(10) Uani 1 1 d . . . C38 C 0.5158(4) -0.1187(3) 0.0683(2) 0.0263(10) Uani 1 1 d . . . H38A H 0.5902 -0.0887 0.0726 0.032 Uiso 1 1 calc R . . C34 C 0.2958(5) -0.1264(3) 0.0540(2) 0.0277(10) Uani 1 1 d . . . H34A H 0.2159 -0.1020 0.0488 0.033 Uiso 1 1 calc R . . C36 C 0.4174(5) -0.2421(2) 0.0657(2) 0.0275(10) Uani 1 1 d . . . N5 N 0.4214(4) -0.3174(2) 0.0692(2) 0.0380(11) Uani 1 1 d . . . C5 C -0.1989(5) 0.0400(3) 0.0824(3) 0.0366(13) Uani 1 1 d . . . H5A H -0.2638 0.0343 0.1114 0.044 Uiso 1 1 calc R . . C32 C 0.4629(4) -0.0181(3) -0.0810(2) 0.0257(10) Uani 1 1 d . . . H32A H 0.4600 -0.0630 -0.0578 0.031 Uiso 1 1 calc R . . C31 C 0.5281(5) -0.0174(3) -0.1344(2) 0.0318(11) Uani 1 1 d . . . H31A H 0.5701 -0.0618 -0.1479 0.038 Uiso 1 1 calc R . . C35 C 0.3003(5) -0.2033(3) 0.0558(2) 0.0302(11) Uani 1 1 d . . . H35A H 0.2243 -0.2316 0.0503 0.036 Uiso 1 1 calc R . . C1 C 0.2007(4) 0.0506(2) -0.00038(19) 0.0188(9) Uani 1 1 d . . . C22 C 0.4781(5) 0.2023(3) 0.1379(2) 0.0330(12) Uani 1 1 d . . . H22A H 0.4876 0.1937 0.1792 0.040 Uiso 1 1 calc R . . C17 C 0.2046(5) 0.1072(3) 0.2505(2) 0.0354(12) Uani 1 1 d . . . H17A H 0.1684 0.1491 0.2709 0.042 Uiso 1 1 calc R . . C25 C 0.4459(5) 0.2279(2) 0.0196(2) 0.0266(10) Uani 1 1 d . . . C18 C 0.2046(5) 0.1057(3) 0.1885(2) 0.0242(10) Uani 1 1 d . . . C28 C 0.4024(5) 0.1141(2) -0.09437(19) 0.0228(9) Uani 1 1 d . . . C23 C 0.5798(5) 0.1924(3) 0.0992(3) 0.0357(12) Uani 1 1 d . . . H23A H 0.6600 0.1762 0.1139 0.043 Uiso 1 1 calc R . . C26 C 0.4214(5) 0.2447(2) -0.0455(2) 0.0296(11) Uani 1 1 d . . . H26A H 0.5041 0.2469 -0.0665 0.036 Uiso 1 1 calc R . . H26B H 0.3809 0.2951 -0.0489 0.036 Uiso 1 1 calc R . . F3 F 0.3338(5) 0.6225(2) 0.8395(2) 0.0969(17) Uani 1 1 d . . . C29 C 0.4687(5) 0.1120(3) -0.1482(2) 0.0293(11) Uani 1 1 d . . . H29A H 0.4704 0.1562 -0.1721 0.035 Uiso 1 1 calc R . . C6 C -0.2346(5) 0.0504(3) 0.0246(3) 0.0314(12) Uani 1 1 d . . . H6A H -0.3223 0.0517 0.0144 0.038 Uiso 1 1 calc R . . O3 O 0.5407(4) 0.7882(2) 0.8729(2) 0.0600(12) Uani 1 1 d . . . C14 C 0.3056(6) -0.0180(3) 0.1935(2) 0.0423(14) Uani 1 1 d . . . H14A H 0.3389 -0.0613 0.1739 0.051 Uiso 1 1 calc R . . C15 C 0.3062(7) -0.0150(4) 0.2538(2) 0.0570(19) Uani 1 1 d . . . H15A H 0.3402 -0.0559 0.2761 0.068 Uiso 1 1 calc R . . C19 C 0.1547(5) 0.1742(2) 0.1549(2) 0.0257(10) Uani 1 1 d . . . H19A H 0.0746 0.1914 0.1736 0.031 Uiso 1 1 calc R . . H19B H 0.1349 0.1590 0.1137 0.031 Uiso 1 1 calc R . . C11 C 0.0703(5) 0.0704(2) -0.0990(2) 0.0274(11) Uani 1 1 d . . . H11A H 0.1390 0.0743 -0.1262 0.033 Uiso 1 1 calc R . . C24 C 0.5645(5) 0.2059(3) 0.0400(2) 0.0334(12) Uani 1 1 d . . . H24A H 0.6339 0.2003 0.0134 0.040 Uiso 1 1 calc R . . C13 C 0.2561(5) 0.0424(3) 0.1599(2) 0.0254(10) Uani 1 1 d . . . F2 F 0.4080(6) 0.7071(2) 0.77989(18) 0.0967(17) Uani 1 1 d . . . C37 C 0.5276(5) -0.1954(3) 0.0713(2) 0.0300(11) Uani 1 1 d . . . H37A H 0.6089 -0.2177 0.0772 0.036 Uiso 1 1 calc R . . C39 C 0.3102(6) -0.3642(3) 0.0552(3) 0.0516(17) Uani 1 1 d . . . H39A H 0.2350 -0.3318 0.0513 0.077 Uiso 1 1 calc R . . H39B H 0.2964 -0.4008 0.0872 0.077 Uiso 1 1 calc R . . H39C H 0.3250 -0.3912 0.0179 0.077 Uiso 1 1 calc R . . C40 C 0.5438(6) -0.3571(3) 0.0763(3) 0.0490(16) Uani 1 1 d . . . H40A H 0.6105 -0.3205 0.0861 0.074 Uiso 1 1 calc R . . H40B H 0.5657 -0.3830 0.0393 0.074 Uiso 1 1 calc R . . H40C H 0.5366 -0.3944 0.1083 0.074 Uiso 1 1 calc R . . C30 C 0.5319(5) 0.0479(3) -0.1679(2) 0.0300(11) Uani 1 1 d . . . H30A H 0.5776 0.0489 -0.2042 0.036 Uiso 1 1 calc R . . C10 C -0.0576(5) 0.0765(3) -0.1189(2) 0.0333(12) Uani 1 1 d . . . H10A H -0.0732 0.0848 -0.1598 0.040 Uiso 1 1 calc R . . C9 C -0.1594(5) 0.0708(3) -0.0811(3) 0.0345(13) Uani 1 1 d . . . H9A H -0.2435 0.0747 -0.0963 0.041 Uiso 1 1 calc R . . C16 C 0.2574(6) 0.0476(4) 0.2825(3) 0.0482(15) Uani 1 1 d . . . H16A H 0.2598 0.0500 0.3245 0.058 Uiso 1 1 calc R . . C27 C 0.3368(5) 0.1863(2) -0.0761(2) 0.0261(11) Uani 1 1 d . . . H27A H 0.2659 0.1733 -0.0491 0.031 Uiso 1 1 calc R . . H27B H 0.2992 0.2099 -0.1118 0.031 Uiso 1 1 calc R . . F1 F 0.5330(6) 0.6316(3) 0.8227(2) 0.0928(16) Uani 1 1 d . . . O2 O 0.4836(5) 0.6886(3) 0.9393(2) 0.0777(16) Uani 1 1 d . . . C20 C 0.2497(5) 0.2409(3) 0.1536(2) 0.0294(11) Uani 1 1 d . . . H20A H 0.2053 0.2869 0.1394 0.035 Uiso 1 1 calc R . . H20B H 0.2803 0.2509 0.1943 0.035 Uiso 1 1 calc R . . O1 O 0.3203(5) 0.7710(3) 0.8956(3) 0.0805(16) Uani 1 1 d . . . C42 C 0.4305(8) 0.6727(3) 0.8305(3) 0.0552(18) Uani 1 1 d . . . Cl2 Cl 0.6646(6) 0.2715(2) 0.2697(2) 0.212(3) Uani 1 1 d DU A . C41 C 0.7162(13) 0.1744(9) 0.2702(7) 0.189(9) Uani 1 1 d . . . Cl3 Cl 0.8336(4) 0.1667(3) 0.22181(17) 0.0816(17) Uani 0.483(5) 1 d PD A 1 Cl1 Cl 0.6232(4) 0.1144(3) 0.28753(16) 0.0874(17) Uani 0.517(5) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0188(6) 0.0158(5) 0.0264(6) 0.0018(4) -0.0005(5) 0.0002(5) S1 0.0398(8) 0.0457(8) 0.0456(8) -0.0040(6) 0.0044(7) -0.0006(6) N4 0.0224(19) 0.0148(15) 0.029(2) 0.0031(15) -0.0026(19) 0.0000(15) C12 0.021(2) 0.0142(19) 0.030(2) -0.0007(16) -0.004(2) 0.0006(18) N2 0.025(2) 0.0196(18) 0.0212(19) 0.0054(15) 0.0024(16) 0.0003(16) C4 0.030(3) 0.020(2) 0.040(3) 0.001(2) 0.014(2) -0.001(2) C3 0.023(2) 0.0139(18) 0.035(2) 0.0018(19) 0.006(2) 0.0024(17) C7 0.027(3) 0.013(2) 0.042(3) -0.0024(19) -0.002(2) -0.0039(19) N3 0.025(2) 0.0168(16) 0.033(2) -0.0004(17) 0.0022(19) -0.0013(16) C8 0.022(2) 0.013(2) 0.033(2) -0.0018(18) 0.001(2) -0.0003(18) C2 0.020(2) 0.0156(19) 0.026(2) 0.0009(18) 0.002(2) 0.0037(17) C33 0.017(2) 0.0195(19) 0.026(2) -0.0002(18) 0.005(2) -0.0004(18) N1 0.0187(19) 0.0180(17) 0.0224(19) 0.0025(15) 0.0028(16) 0.0005(15) C21 0.030(3) 0.0125(19) 0.037(3) -0.0033(19) 0.002(2) -0.0020(18) C38 0.019(2) 0.025(2) 0.035(3) 0.002(2) 0.001(2) -0.0004(19) C34 0.021(2) 0.024(2) 0.038(3) 0.000(2) -0.004(2) 0.0022(19) C36 0.031(3) 0.0172(19) 0.035(3) 0.0028(18) 0.003(2) 0.003(2) N5 0.041(3) 0.0191(18) 0.054(3) 0.0026(18) 0.004(2) 0.0045(19) C5 0.025(3) 0.022(2) 0.062(4) -0.001(2) 0.015(3) -0.003(2) C32 0.024(2) 0.022(2) 0.031(2) 0.0030(19) 0.001(2) 0.002(2) C31 0.033(3) 0.031(2) 0.032(3) -0.008(2) 0.009(2) 0.009(2) C35 0.025(3) 0.018(2) 0.048(3) -0.002(2) -0.001(2) -0.0014(19) C1 0.016(2) 0.018(2) 0.023(2) 0.0001(17) 0.0036(18) 0.0027(17) C22 0.034(3) 0.020(2) 0.045(3) -0.001(2) -0.010(2) -0.002(2) C17 0.041(3) 0.036(3) 0.028(3) -0.002(2) 0.008(2) 0.004(2) C25 0.026(2) 0.015(2) 0.038(3) -0.0019(19) 0.005(2) -0.0047(19) C18 0.025(2) 0.023(2) 0.024(2) -0.0017(19) 0.0018(19) 0.0006(19) C28 0.024(2) 0.019(2) 0.026(2) 0.0011(17) 0.000(2) -0.0032(19) C23 0.024(3) 0.024(2) 0.060(4) -0.001(2) -0.005(3) 0.001(2) C26 0.037(3) 0.018(2) 0.034(3) 0.0019(18) 0.010(2) -0.003(2) F3 0.112(4) 0.046(2) 0.133(4) 0.005(3) -0.043(4) -0.024(3) C29 0.038(3) 0.023(2) 0.026(2) 0.0042(19) 0.004(2) -0.001(2) C6 0.016(2) 0.019(2) 0.059(4) -0.002(2) 0.001(2) -0.0004(19) O3 0.047(3) 0.044(2) 0.089(3) -0.004(2) 0.009(3) -0.011(2) C14 0.061(4) 0.039(3) 0.026(3) 0.004(2) 0.003(3) 0.025(3) C15 0.089(5) 0.057(4) 0.025(3) 0.006(3) 0.001(3) 0.038(4) C19 0.027(3) 0.021(2) 0.029(2) -0.0005(19) 0.007(2) 0.005(2) C11 0.032(3) 0.022(2) 0.028(2) -0.0050(18) 0.001(2) 0.000(2) C24 0.024(3) 0.020(2) 0.055(3) -0.002(2) 0.008(2) -0.004(2) C13 0.029(3) 0.028(2) 0.020(2) 0.0023(18) -0.0001(19) 0.003(2) F2 0.173(5) 0.066(3) 0.051(2) 0.007(2) -0.031(3) 0.015(3) C37 0.019(3) 0.026(2) 0.045(3) 0.002(2) -0.002(2) 0.005(2) C39 0.052(4) 0.017(2) 0.086(5) 0.005(3) -0.001(4) -0.007(2) C40 0.043(3) 0.027(3) 0.077(5) 0.009(3) 0.004(3) 0.018(3) C30 0.034(3) 0.033(3) 0.023(2) -0.002(2) 0.008(2) 0.004(2) C10 0.038(3) 0.028(2) 0.035(3) -0.005(2) -0.014(2) 0.002(2) C9 0.029(3) 0.018(2) 0.057(4) -0.003(2) -0.017(3) -0.002(2) C16 0.060(4) 0.056(4) 0.029(3) 0.008(3) -0.005(3) 0.006(3) C27 0.032(3) 0.018(2) 0.029(3) 0.0044(18) 0.001(2) 0.002(2) F1 0.123(4) 0.061(3) 0.094(3) -0.021(2) 0.002(3) 0.037(3) O2 0.082(4) 0.109(4) 0.043(3) 0.020(3) -0.007(3) -0.012(3) C20 0.032(3) 0.021(2) 0.035(3) -0.001(2) 0.001(2) 0.005(2) O1 0.041(3) 0.077(3) 0.124(5) -0.022(3) 0.011(3) 0.009(3) C42 0.082(5) 0.035(3) 0.049(4) 0.007(3) -0.016(4) 0.003(3) Cl2 0.327(7) 0.123(3) 0.185(4) -0.049(3) -0.138(4) 0.053(4) C41 0.161(12) 0.198(13) 0.208(14) 0.170(12) 0.131(11) 0.118(10) Cl3 0.043(2) 0.157(5) 0.045(2) -0.016(2) 0.0119(16) -0.013(2) Cl1 0.094(3) 0.113(3) 0.055(2) 0.001(2) 0.013(2) -0.058(3) _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 P1 N1 1.697(4) . ? P1 N2 1.703(4) . ? P1 N4 1.854(3) . ? S1 O3 1.421(5) . ? S1 O1 1.424(5) . ? S1 O2 1.440(5) . ? S1 C42 1.806(7) . ? N4 C38 1.357(6) . ? N4 C34 1.364(6) . ? C12 C11 1.374(6) . ? C12 C8 1.432(7) . ? C12 C1 1.448(6) . ? N2 C2 1.402(6) . ? N2 C13 1.438(6) . ? C4 C3 1.371(7) . ? C4 C5 1.417(7) . ? C4 H4A 0.9500 . ? C3 C8 1.412(7) . ? C3 C2 1.463(6) . ? C7 C8 1.394(7) . ? C7 C9 1.407(8) . ? C7 C6 1.420(7) . ? N3 C21 1.339(6) . ? N3 C25 1.350(6) . ? C2 C1 1.357(6) . ? C33 C28 1.390(6) . ? C33 C32 1.403(6) . ? C33 N1 1.448(6) . ? N1 C1 1.409(6) . ? C21 C22 1.395(7) . ? C21 C20 1.501(7) . ? C38 C37 1.361(6) . ? C38 H38A 0.9500 . ? C34 C35 1.361(6) . ? C34 H34A 0.9500 . ? C36 N5 1.332(6) . ? C36 C35 1.426(7) . ? C36 C37 1.428(7) . ? N5 C39 1.465(7) . ? N5 C40 1.475(7) . ? C5 C6 1.370(8) . ? C5 H5A 0.9500 . ? C32 C31 1.387(7) . ? C32 H32A 0.9500 . ? C31 C30 1.381(7) . ? C31 H31A 0.9500 . ? C35 H35A 0.9500 . ? C22 C23 1.391(8) . ? C22 H22A 0.9500 . ? C17 C16 1.391(8) . ? C17 C18 1.401(7) . ? C17 H17A 0.9500 . ? C25 C24 1.384(7) . ? C25 C26 1.522(7) . ? C18 C13 1.401(6) . ? C18 C19 1.521(6) . ? C28 C29 1.401(7) . ? C28 C27 1.507(6) . ? C23 C24 1.367(8) . ? C23 H23A 0.9500 . ? C26 C27 1.526(7) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? F3 C42 1.364(9) . ? C29 C30 1.385(7) . ? C29 H29A 0.9500 . ? C6 H6A 0.9500 . ? C14 C15 1.362(8) . ? C14 C13 1.409(7) . ? C14 H14A 0.9500 . ? C15 C16 1.381(9) . ? C15 H15A 0.9500 . ? C19 C20 1.544(7) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C11 C10 1.421(7) . ? C11 H11A 0.9500 . ? C24 H24A 0.9500 . ? F2 C42 1.316(7) . ? C37 H37A 0.9500 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C30 H30A 0.9500 . ? C10 C9 1.373(8) . ? C10 H10A 0.9500 . ? C9 H9A 0.9500 . ? C16 H16A 0.9500 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? F1 C42 1.311(8) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? Cl2 C41 1.799(13) . ? C41 Cl1 1.493(15) . ? C41 Cl3 1.653(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 N1 P1 N2 90.68(18) . . ? N1 P1 N4 103.26(18) . . ? N2 P1 N4 99.20(18) . . ? O3 S1 O1 114.3(3) . . ? O3 S1 O2 113.1(3) . . ? O1 S1 O2 118.1(4) . . ? O3 S1 C42 102.8(3) . . ? O1 S1 C42 103.8(3) . . ? O2 S1 C42 102.0(3) . . ? C38 N4 C34 118.4(4) . . ? C38 N4 P1 117.4(3) . . ? C34 N4 P1 124.1(3) . . ? C11 C12 C8 118.0(4) . . ? C11 C12 C1 138.3(5) . . ? C8 C12 C1 103.7(4) . . ? C2 N2 C13 126.2(4) . . ? C2 N2 P1 111.7(3) . . ? C13 N2 P1 122.1(3) . . ? C3 C4 C5 117.4(5) . . ? C3 C4 H4A 121.3 . . ? C5 C4 H4A 121.3 . . ? C4 C3 C8 119.1(4) . . ? C4 C3 C2 137.0(5) . . ? C8 C3 C2 103.9(4) . . ? C8 C7 C9 116.6(5) . . ? C8 C7 C6 115.6(5) . . ? C9 C7 C6 127.8(5) . . ? C21 N3 C25 118.4(4) . . ? C7 C8 C3 124.3(4) . . ? C7 C8 C12 123.6(4) . . ? C3 C8 C12 112.1(4) . . ? C1 C2 N2 112.4(4) . . ? C1 C2 C3 109.8(4) . . ? N2 C2 C3 137.7(4) . . ? C28 C33 C32 121.7(4) . . ? C28 C33 N1 120.2(4) . . ? C32 C33 N1 118.0(4) . . ? C1 N1 C33 123.4(4) . . ? C1 N1 P1 111.9(3) . . ? C33 N1 P1 124.2(3) . . ? N3 C21 C22 122.4(5) . . ? N3 C21 C20 116.7(4) . . ? C22 C21 C20 120.8(5) . . ? N4 C38 C37 123.1(4) . . ? N4 C38 H38A 118.4 . . ? C37 C38 H38A 118.4 . . ? C35 C34 N4 121.8(4) . . ? C35 C34 H34A 119.1 . . ? N4 C34 H34A 119.1 . . ? N5 C36 C35 121.1(4) . . ? N5 C36 C37 123.1(4) . . ? C35 C36 C37 115.8(4) . . ? C36 N5 C39 121.7(5) . . ? C36 N5 C40 120.6(5) . . ? C39 N5 C40 116.7(4) . . ? C6 C5 C4 123.6(5) . . ? C6 C5 H5A 118.2 . . ? C4 C5 H5A 118.2 . . ? C31 C32 C33 119.7(4) . . ? C31 C32 H32A 120.2 . . ? C33 C32 H32A 120.2 . . ? C30 C31 C32 119.9(4) . . ? C30 C31 H31A 120.0 . . ? C32 C31 H31A 120.0 . . ? C34 C35 C36 121.0(4) . . ? C34 C35 H35A 119.5 . . ? C36 C35 H35A 119.5 . . ? C2 C1 N1 112.0(4) . . ? C2 C1 C12 110.5(4) . . ? N1 C1 C12 137.5(4) . . ? C23 C22 C21 117.9(5) . . ? C23 C22 H22A 121.0 . . ? C21 C22 H22A 121.0 . . ? C16 C17 C18 120.3(5) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? N3 C25 C24 122.5(5) . . ? N3 C25 C26 115.6(4) . . ? C24 C25 C26 121.9(4) . . ? C13 C18 C17 118.4(4) . . ? C13 C18 C19 122.6(4) . . ? C17 C18 C19 118.9(4) . . ? C33 C28 C29 116.6(4) . . ? C33 C28 C27 124.3(4) . . ? C29 C28 C27 119.2(4) . . ? C24 C23 C22 120.1(5) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C25 C26 C27 113.8(4) . . ? C25 C26 H26A 108.8 . . ? C27 C26 H26A 108.8 . . ? C25 C26 H26B 108.8 . . ? C27 C26 H26B 108.8 . . ? H26A C26 H26B 107.7 . . ? C30 C29 C28 122.6(4) . . ? C30 C29 H29A 118.7 . . ? C28 C29 H29A 118.7 . . ? C5 C6 C7 120.0(5) . . ? C5 C6 H6A 120.0 . . ? C7 C6 H6A 120.0 . . ? C15 C14 C13 120.7(5) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C14 C15 C16 119.9(5) . . ? C14 C15 H15A 120.1 . . ? C16 C15 H15A 120.1 . . ? C18 C19 C20 113.2(4) . . ? C18 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? C18 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C12 C11 C10 118.8(5) . . ? C12 C11 H11A 120.6 . . ? C10 C11 H11A 120.6 . . ? C23 C24 C25 118.7(5) . . ? C23 C24 H24A 120.7 . . ? C25 C24 H24A 120.7 . . ? C18 C13 C14 120.0(4) . . ? C18 C13 N2 122.3(4) . . ? C14 C13 N2 117.7(4) . . ? C38 C37 C36 119.8(4) . . ? C38 C37 H37A 120.1 . . ? C36 C37 H37A 120.1 . . ? N5 C39 H39A 109.5 . . ? N5 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N5 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? N5 C40 H40A 109.5 . . ? N5 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? N5 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C31 C30 C29 119.5(4) . . ? C31 C30 H30A 120.2 . . ? C29 C30 H30A 120.2 . . ? C9 C10 C11 122.3(5) . . ? C9 C10 H10A 118.8 . . ? C11 C10 H10A 118.8 . . ? C10 C9 C7 120.7(5) . . ? C10 C9 H9A 119.7 . . ? C7 C9 H9A 119.7 . . ? C15 C16 C17 120.8(5) . . ? C15 C16 H16A 119.6 . . ? C17 C16 H16A 119.6 . . ? C28 C27 C26 115.4(4) . . ? C28 C27 H27A 108.4 . . ? C26 C27 H27A 108.4 . . ? C28 C27 H27B 108.4 . . ? C26 C27 H27B 108.4 . . ? H27A C27 H27B 107.5 . . ? C21 C20 C19 112.3(4) . . ? C21 C20 H20A 109.1 . . ? C19 C20 H20A 109.1 . . ? C21 C20 H20B 109.1 . . ? C19 C20 H20B 109.1 . . ? H20A C20 H20B 107.9 . . ? F1 C42 F2 106.6(6) . . ? F1 C42 F3 105.8(5) . . ? F2 C42 F3 107.2(6) . . ? F1 C42 S1 113.2(5) . . ? F2 C42 S1 112.7(4) . . ? F3 C42 S1 110.9(5) . . ? Cl1 C41 Cl3 127.1(12) . . ? Cl1 C41 Cl2 118.7(7) . . ? Cl3 C41 Cl2 107.4(6) . . ? 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 N1 P1 N4 C38 125.9(3) . . . . ? N2 P1 N4 C38 -141.2(4) . . . . ? N1 P1 N4 C34 -58.2(4) . . . . ? N2 P1 N4 C34 34.7(4) . . . . ? N1 P1 N2 C2 11.0(3) . . . . ? N4 P1 N2 C2 -92.6(3) . . . . ? N1 P1 N2 C13 -166.7(3) . . . . ? N4 P1 N2 C13 89.7(4) . . . . ? C5 C4 C3 C8 -0.8(6) . . . . ? C5 C4 C3 C2 -179.2(5) . . . . ? C9 C7 C8 C3 178.1(4) . . . . ? C6 C7 C8 C3 -3.1(6) . . . . ? C9 C7 C8 C12 -1.5(6) . . . . ? C6 C7 C8 C12 177.3(4) . . . . ? C4 C3 C8 C7 2.7(7) . . . . ? C2 C3 C8 C7 -178.5(4) . . . . ? C4 C3 C8 C12 -177.7(4) . . . . ? C2 C3 C8 C12 1.2(5) . . . . ? C11 C12 C8 C7 1.8(6) . . . . ? C1 C12 C8 C7 -179.7(4) . . . . ? C11 C12 C8 C3 -177.8(4) . . . . ? C1 C12 C8 C3 0.6(5) . . . . ? C13 N2 C2 C1 168.7(4) . . . . ? P1 N2 C2 C1 -8.9(4) . . . . ? C13 N2 C2 C3 -16.7(8) . . . . ? P1 N2 C2 C3 165.8(4) . . . . ? C4 C3 C2 C1 175.8(5) . . . . ? C8 C3 C2 C1 -2.8(5) . . . . ? C4 C3 C2 N2 1.0(9) . . . . ? C8 C3 C2 N2 -177.5(5) . . . . ? C28 C33 N1 C1 66.4(6) . . . . ? C32 C33 N1 C1 -112.8(5) . . . . ? C28 C33 N1 P1 -122.5(4) . . . . ? C32 C33 N1 P1 58.3(5) . . . . ? N2 P1 N1 C1 -10.4(3) . . . . ? N4 P1 N1 C1 89.3(3) . . . . ? N2 P1 N1 C33 177.6(3) . . . . ? N4 P1 N1 C33 -82.8(3) . . . . ? C25 N3 C21 C22 -1.0(6) . . . . ? C25 N3 C21 C20 176.7(4) . . . . ? C34 N4 C38 C37 0.9(7) . . . . ? P1 N4 C38 C37 176.9(4) . . . . ? C38 N4 C34 C35 -1.7(7) . . . . ? P1 N4 C34 C35 -177.5(4) . . . . ? C35 C36 N5 C39 8.4(8) . . . . ? C37 C36 N5 C39 -171.6(5) . . . . ? C35 C36 N5 C40 176.8(5) . . . . ? C37 C36 N5 C40 -3.1(8) . . . . ? C3 C4 C5 C6 -0.4(7) . . . . ? C28 C33 C32 C31 0.7(7) . . . . ? N1 C33 C32 C31 179.9(4) . . . . ? C33 C32 C31 C30 -0.1(7) . . . . ? N4 C34 C35 C36 2.4(8) . . . . ? N5 C36 C35 C34 178.0(5) . . . . ? C37 C36 C35 C34 -2.1(7) . . . . ? N2 C2 C1 N1 1.1(5) . . . . ? C3 C2 C1 N1 -175.1(3) . . . . ? N2 C2 C1 C12 179.5(3) . . . . ? C3 C2 C1 C12 3.3(5) . . . . ? C33 N1 C1 C2 179.3(4) . . . . ? P1 N1 C1 C2 7.2(4) . . . . ? C33 N1 C1 C12 1.5(8) . . . . ? P1 N1 C1 C12 -170.6(4) . . . . ? C11 C12 C1 C2 175.5(5) . . . . ? C8 C12 C1 C2 -2.4(5) . . . . ? C11 C12 C1 N1 -6.6(9) . . . . ? C8 C12 C1 N1 175.4(5) . . . . ? N3 C21 C22 C23 0.5(7) . . . . ? C20 C21 C22 C23 -177.0(4) . . . . ? C21 N3 C25 C24 0.2(6) . . . . ? C21 N3 C25 C26 -178.3(4) . . . . ? C16 C17 C18 C13 1.4(8) . . . . ? C16 C17 C18 C19 -175.7(5) . . . . ? C32 C33 C28 C29 -0.3(7) . . . . ? N1 C33 C28 C29 -179.5(4) . . . . ? C32 C33 C28 C27 179.2(4) . . . . ? N1 C33 C28 C27 0.0(7) . . . . ? C21 C22 C23 C24 0.7(7) . . . . ? N3 C25 C26 C27 -70.9(5) . . . . ? C24 C25 C26 C27 110.5(5) . . . . ? C33 C28 C29 C30 -0.8(7) . . . . ? C27 C28 C29 C30 179.7(5) . . . . ? C4 C5 C6 C7 -0.1(8) . . . . ? C8 C7 C6 C5 1.7(7) . . . . ? C9 C7 C6 C5 -179.6(5) . . . . ? C13 C14 C15 C16 0.3(11) . . . . ? C13 C18 C19 C20 -100.3(5) . . . . ? C17 C18 C19 C20 76.7(6) . . . . ? C8 C12 C11 C10 -0.9(6) . . . . ? C1 C12 C11 C10 -178.6(5) . . . . ? C22 C23 C24 C25 -1.4(7) . . . . ? N3 C25 C24 C23 1.0(7) . . . . ? C26 C25 C24 C23 179.4(4) . . . . ? C17 C18 C13 C14 0.4(7) . . . . ? C19 C18 C13 C14 177.4(5) . . . . ? C17 C18 C13 N2 -178.5(5) . . . . ? C19 C18 C13 N2 -1.5(7) . . . . ? C15 C14 C13 C18 -1.3(9) . . . . ? C15 C14 C13 N2 177.7(6) . . . . ? C2 N2 C13 C18 -53.9(7) . . . . ? P1 N2 C13 C18 123.5(4) . . . . ? C2 N2 C13 C14 127.2(5) . . . . ? P1 N2 C13 C14 -55.4(6) . . . . ? N4 C38 C37 C36 -0.7(8) . . . . ? N5 C36 C37 C38 -178.9(5) . . . . ? C35 C36 C37 C38 1.2(7) . . . . ? C32 C31 C30 C29 -1.0(8) . . . . ? C28 C29 C30 C31 1.5(8) . . . . ? C12 C11 C10 C9 -0.3(7) . . . . ? C11 C10 C9 C7 0.7(7) . . . . ? C8 C7 C9 C10 0.2(7) . . . . ? C6 C7 C9 C10 -178.4(5) . . . . ? C14 C15 C16 C17 1.5(11) . . . . ? C18 C17 C16 C15 -2.4(10) . . . . ? C33 C28 C27 C26 97.0(5) . . . . ? C29 C28 C27 C26 -83.5(5) . . . . ? C25 C26 C27 C28 -79.5(5) . . . . ? N3 C21 C20 C19 82.1(5) . . . . ? C22 C21 C20 C19 -100.2(5) . . . . ? C18 C19 C20 C21 71.5(5) . . . . ? O3 S1 C42 F1 65.5(5) . . . . ? O1 S1 C42 F1 -175.1(5) . . . . ? O2 S1 C42 F1 -51.9(6) . . . . ? O3 S1 C42 F2 -55.6(7) . . . . ? O1 S1 C42 F2 63.8(7) . . . . ? O2 S1 C42 F2 -173.0(6) . . . . ? O3 S1 C42 F3 -175.7(4) . . . . ? O1 S1 C42 F3 -56.3(5) . . . . ? O2 S1 C42 F3 66.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.025 _refine_diff_density_min -0.714 _refine_diff_density_rms 0.097 # Attachment '- Ragogna_clammy_submit.cif' data_2[I3] _database_code_depnum_ccdc_archive 'CCDC 789696' #TrackingRef '- Ragogna_clammy_submit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 N3 P, C H2 Cl2, I3' _chemical_formula_sum 'C34 H27 Cl2 I3 N3 P' _chemical_formula_weight 960.16 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.811(2) _cell_length_b 12.371(3) _cell_length_c 13.303(3) _cell_angle_alpha 82.17(3) _cell_angle_beta 82.44(3) _cell_angle_gamma 77.46(3) _cell_volume 1711.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 41494 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.864 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 2.972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6168 _exptl_absorpt_correction_T_max 0.6986 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12182 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.68 _reflns_number_total 6494 _reflns_number_gt 5636 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0651P)^2^+10.4146P] 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_number_reflns 6494 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1534 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.198 _refine_ls_restrained_S_all 1.198 _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 I2 I 0.76140(5) 0.51313(4) 0.41456(4) 0.04079(16) Uani 1 1 d . . . P1 P 0.73706(16) 0.92156(14) 0.80391(12) 0.0255(3) Uani 1 1 d . . . N2 N 0.8014(5) 0.8392(4) 0.7117(4) 0.0222(10) Uani 1 1 d . . . C18 C 0.7381(6) 0.6665(5) 0.6881(5) 0.0248(13) Uani 1 1 d . . . N1 N 0.7389(5) 1.0359(4) 0.7186(4) 0.0225(11) Uani 1 1 d . . . C31 C 0.6899(7) 1.2818(6) 0.8623(5) 0.0324(15) Uani 1 1 d . . . H31A H 0.7283 1.3062 0.9130 0.039 Uiso 1 1 calc R . . N3 N 0.4449(5) 0.9352(5) 0.7009(5) 0.0321(13) Uani 1 1 d . . . C2 C 0.8228(5) 0.8982(5) 0.6190(5) 0.0218(12) Uani 1 1 d . . . C6 C 0.9367(6) 0.9003(6) 0.3039(5) 0.0316(15) Uani 1 1 d . . . H6A H 0.9596 0.9068 0.2322 0.038 Uiso 1 1 calc R . . C13 C 0.8218(6) 0.7187(5) 0.7261(5) 0.0236(13) Uani 1 1 d . . . C12 C 0.8102(6) 1.0697(5) 0.5198(4) 0.0219(12) Uani 1 1 d . . . C17 C 0.7637(7) 0.5497(6) 0.7036(5) 0.0306(14) Uani 1 1 d . . . H17A H 0.7098 0.5106 0.6785 0.037 Uiso 1 1 calc R . . C3 C 0.8699(6) 0.8738(5) 0.5150(5) 0.0239(13) Uani 1 1 d . . . C32 C 0.7426(6) 1.1789(6) 0.8245(5) 0.0278(13) Uani 1 1 d . . . H32A H 0.8169 1.1328 0.8498 0.033 Uiso 1 1 calc R . . C33 C 0.6853(6) 1.1455(5) 0.7504(5) 0.0230(12) Uani 1 1 d . . . C1 C 0.7863(5) 1.0115(5) 0.6227(5) 0.0210(12) Uani 1 1 d . . . C14 C 0.9249(6) 0.6601(6) 0.7766(5) 0.0293(14) Uani 1 1 d . . . H14A H 0.9799 0.6984 0.8013 0.035 Uiso 1 1 calc R . . C9 C 0.8744(6) 1.1108(6) 0.3089(5) 0.0303(14) Uani 1 1 d . . . H9A H 0.8953 1.1268 0.2376 0.036 Uiso 1 1 calc R . . C8 C 0.8590(5) 0.9812(5) 0.4588(5) 0.0225(12) Uani 1 1 d . . . C28 C 0.5747(6) 1.2094(5) 0.7112(5) 0.0272(13) Uani 1 1 d . . . C4 C 0.9159(6) 0.7793(6) 0.4655(5) 0.0271(13) Uani 1 1 d . . . H4A H 0.9255 0.7067 0.5017 0.033 Uiso 1 1 calc R . . C27 C 0.5054(6) 1.1737(6) 0.6339(5) 0.0298(14) Uani 1 1 d . . . H27A H 0.5626 1.1114 0.6011 0.036 Uiso 1 1 calc R . . H27B H 0.4851 1.2366 0.5802 0.036 Uiso 1 1 calc R . . C15 C 0.9457(7) 0.5447(6) 0.7901(6) 0.0358(16) Uani 1 1 d . . . H15A H 1.0158 0.5032 0.8242 0.043 Uiso 1 1 calc R . . C11 C 0.7955(6) 1.1778(5) 0.4749(5) 0.0252(13) Uani 1 1 d . . . H11A H 0.7642 1.2385 0.5143 0.030 Uiso 1 1 calc R . . C7 C 0.8912(6) 0.9978(6) 0.3539(5) 0.0270(13) Uani 1 1 d . . . C19 C 0.6263(6) 0.7284(6) 0.6321(5) 0.0291(14) Uani 1 1 d . . . H19A H 0.6237 0.6903 0.5719 0.035 Uiso 1 1 calc R . . H19B H 0.6393 0.8046 0.6072 0.035 Uiso 1 1 calc R . . C25 C 0.4050(6) 1.0278(6) 0.7486(6) 0.0326(15) Uani 1 1 d . . . C30 C 0.5823(7) 1.3463(6) 0.8246(6) 0.0363(16) Uani 1 1 d . . . H30A H 0.5463 1.4161 0.8494 0.044 Uiso 1 1 calc R . . C21 C 0.4612(6) 0.8352(6) 0.7564(6) 0.0346(16) Uani 1 1 d . . . C29 C 0.5254(7) 1.3110(6) 0.7510(6) 0.0326(15) Uani 1 1 d . . . H29A H 0.4506 1.3571 0.7268 0.039 Uiso 1 1 calc R . . C16 C 0.8649(7) 0.4898(6) 0.7542(6) 0.0356(16) Uani 1 1 d . . . H16A H 0.8790 0.4108 0.7644 0.043 Uiso 1 1 calc R . . C5 C 0.9480(6) 0.7954(6) 0.3589(5) 0.0319(15) Uani 1 1 d . . . H5A H 0.9786 0.7318 0.3233 0.038 Uiso 1 1 calc R . . C20 C 0.4979(6) 0.7364(6) 0.6977(7) 0.0378(17) Uani 1 1 d . . . H20A H 0.4309 0.7390 0.6528 0.045 Uiso 1 1 calc R . . H20B H 0.5009 0.6680 0.7463 0.045 Uiso 1 1 calc R . . C10 C 0.8284(6) 1.1963(6) 0.3676(5) 0.0301(14) Uani 1 1 d . . . H10A H 0.8181 1.2707 0.3356 0.036 Uiso 1 1 calc R . . C26 C 0.3815(7) 1.1366(6) 0.6807(6) 0.0368(16) Uani 1 1 d . . . H26A H 0.3289 1.1950 0.7210 0.044 Uiso 1 1 calc R . . H26B H 0.3327 1.1287 0.6251 0.044 Uiso 1 1 calc R . . C24 C 0.3860(8) 1.0230(7) 0.8543(6) 0.0440(19) Uani 1 1 d . . . H24A H 0.3610 1.0893 0.8869 0.053 Uiso 1 1 calc R . . C23 C 0.4044(9) 0.9190(8) 0.9115(7) 0.052(2) Uani 1 1 d . . . H23A H 0.3915 0.9133 0.9839 0.062 Uiso 1 1 calc R . . C22 C 0.4414(8) 0.8247(7) 0.8625(7) 0.0449(19) Uani 1 1 d . . . H22A H 0.4533 0.7531 0.9005 0.054 Uiso 1 1 calc R . . I3 I 0.0000 0.0000 1.0000 0.0456(2) Uani 1 2 d S . . I4 I 0.04667(6) 0.22706(5) 0.96372(5) 0.0566(2) Uani 1 1 d . . . Cl1 Cl 0.2761(3) 0.5857(3) 0.8739(2) 0.0785(8) Uani 1 1 d . . . Cl2 Cl 0.3414(3) 0.4070(4) 1.0317(2) 0.1192(17) Uani 1 1 d . . . C34 C 0.2344(13) 0.4763(15) 0.9522(11) 0.106(5) Uani 1 1 d . . . H34A H 0.1537 0.5040 0.9938 0.128 Uiso 1 1 calc R . . H34B H 0.2173 0.4228 0.9094 0.128 Uiso 1 1 calc R . . I1 I 0.5000 0.5000 0.5000 0.03179(17) Uani 1 2 d S . . 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 I2 0.0385(3) 0.0363(3) 0.0469(3) -0.0080(2) 0.0017(2) -0.0077(2) P1 0.0282(8) 0.0266(8) 0.0195(8) -0.0004(6) 0.0006(6) -0.0038(7) N2 0.019(2) 0.026(3) 0.020(3) -0.001(2) 0.0001(19) -0.004(2) C18 0.024(3) 0.025(3) 0.025(3) -0.004(2) 0.002(2) -0.005(3) N1 0.020(2) 0.027(3) 0.020(3) -0.001(2) 0.000(2) -0.006(2) C31 0.037(4) 0.036(4) 0.025(3) -0.007(3) 0.003(3) -0.012(3) N3 0.021(3) 0.033(3) 0.042(3) 0.002(3) -0.003(2) -0.007(2) C2 0.017(3) 0.029(3) 0.020(3) 0.000(2) -0.003(2) -0.006(2) C6 0.026(3) 0.047(4) 0.022(3) -0.006(3) 0.003(3) -0.009(3) C13 0.025(3) 0.024(3) 0.020(3) 0.002(2) 0.002(2) -0.005(2) C12 0.019(3) 0.030(3) 0.018(3) -0.001(2) 0.001(2) -0.010(2) C17 0.032(3) 0.030(3) 0.032(4) -0.005(3) 0.002(3) -0.011(3) C3 0.019(3) 0.032(3) 0.021(3) -0.004(3) -0.002(2) -0.006(2) C32 0.027(3) 0.032(3) 0.023(3) -0.002(3) 0.001(3) -0.007(3) C33 0.020(3) 0.024(3) 0.022(3) -0.002(2) 0.004(2) -0.004(2) C1 0.016(3) 0.026(3) 0.021(3) -0.001(2) 0.000(2) -0.004(2) C14 0.027(3) 0.030(3) 0.029(3) 0.001(3) 0.000(3) -0.005(3) C9 0.026(3) 0.042(4) 0.023(3) 0.004(3) 0.001(3) -0.014(3) C8 0.013(3) 0.029(3) 0.026(3) 0.000(2) -0.001(2) -0.006(2) C28 0.024(3) 0.028(3) 0.025(3) 0.003(3) 0.002(2) -0.003(3) C4 0.023(3) 0.029(3) 0.030(3) -0.005(3) 0.000(3) -0.005(3) C27 0.024(3) 0.032(4) 0.031(4) 0.005(3) -0.004(3) -0.006(3) C15 0.030(4) 0.037(4) 0.036(4) 0.004(3) -0.002(3) -0.002(3) C11 0.020(3) 0.027(3) 0.028(3) 0.001(3) 0.001(2) -0.009(2) C7 0.019(3) 0.038(4) 0.025(3) -0.004(3) 0.002(2) -0.010(3) C19 0.026(3) 0.028(3) 0.036(4) -0.003(3) -0.007(3) -0.009(3) C25 0.019(3) 0.033(4) 0.044(4) -0.001(3) 0.003(3) -0.007(3) C30 0.041(4) 0.030(4) 0.034(4) -0.007(3) 0.011(3) -0.004(3) C21 0.019(3) 0.037(4) 0.046(4) 0.001(3) 0.002(3) -0.009(3) C29 0.029(3) 0.026(3) 0.037(4) 0.004(3) 0.005(3) -0.003(3) C16 0.041(4) 0.025(3) 0.035(4) 0.002(3) 0.006(3) -0.005(3) C5 0.025(3) 0.041(4) 0.030(4) -0.012(3) 0.004(3) -0.005(3) C20 0.022(3) 0.032(4) 0.061(5) -0.004(3) -0.003(3) -0.009(3) C10 0.028(3) 0.033(4) 0.028(3) 0.007(3) -0.002(3) -0.009(3) C26 0.023(3) 0.034(4) 0.050(4) -0.001(3) -0.005(3) 0.000(3) C24 0.038(4) 0.041(4) 0.048(5) -0.005(4) 0.013(3) -0.007(3) C23 0.055(5) 0.054(5) 0.040(5) 0.002(4) 0.014(4) -0.015(4) C22 0.039(4) 0.037(4) 0.054(5) 0.008(4) 0.006(4) -0.012(3) I3 0.0483(4) 0.0566(5) 0.0223(3) -0.0010(3) -0.0080(3) 0.0110(3) I4 0.0644(4) 0.0581(4) 0.0441(3) -0.0132(3) -0.0155(3) 0.0048(3) Cl1 0.0671(17) 0.085(2) 0.0783(19) -0.0006(15) 0.0081(14) -0.0190(15) Cl2 0.0618(18) 0.202(5) 0.0549(17) 0.028(2) 0.0056(13) 0.024(2) C34 0.064(8) 0.151(14) 0.088(10) 0.038(9) -0.021(7) -0.013(8) I1 0.0417(4) 0.0242(3) 0.0310(3) -0.0019(2) -0.0036(3) -0.0107(3) _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 I2 I1 2.9339(9) . ? P1 N2 1.684(5) . ? P1 N1 1.691(5) . ? N2 C2 1.364(8) . ? N2 C13 1.449(8) . ? C18 C13 1.398(9) . ? C18 C17 1.402(9) . ? C18 C19 1.511(9) . ? N1 C1 1.359(8) . ? N1 C33 1.450(8) . ? C31 C30 1.372(11) . ? C31 C32 1.408(10) . ? C31 H31A 0.9500 . ? N3 C21 1.341(9) . ? N3 C25 1.346(9) . ? C2 C1 1.377(9) . ? C2 C3 1.458(8) . ? C6 C5 1.389(11) . ? C6 C7 1.419(10) . ? C6 H6A 0.9500 . ? C13 C14 1.390(9) . ? C12 C11 1.373(9) . ? C12 C8 1.418(9) . ? C12 C1 1.476(8) . ? C17 C16 1.381(11) . ? C17 H17A 0.9500 . ? C3 C4 1.385(9) . ? C3 C8 1.423(9) . ? C32 C33 1.382(9) . ? C32 H32A 0.9500 . ? C33 C28 1.402(9) . ? C14 C15 1.387(10) . ? C14 H14A 0.9500 . ? C9 C10 1.367(10) . ? C9 C7 1.427(10) . ? C9 H9A 0.9500 . ? C8 C7 1.391(9) . ? C28 C29 1.400(10) . ? C28 C27 1.511(10) . ? C4 C5 1.412(9) . ? C4 H4A 0.9500 . ? C27 C26 1.537(9) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C15 C16 1.380(11) . ? C15 H15A 0.9500 . ? C11 C10 1.425(9) . ? C11 H11A 0.9500 . ? C19 C20 1.530(10) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C25 C24 1.390(11) . ? C25 C26 1.507(10) . ? C30 C29 1.387(11) . ? C30 H30A 0.9500 . ? C21 C22 1.392(12) . ? C21 C20 1.493(11) . ? C29 H29A 0.9500 . ? C16 H16A 0.9500 . ? C5 H5A 0.9500 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C10 H10A 0.9500 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C24 C23 1.392(12) . ? C24 H24A 0.9500 . ? C23 C22 1.372(13) . ? C23 H23A 0.9500 . ? C22 H22A 0.9500 . ? I3 I4 2.9257(9) 2_557 ? I3 I4 2.9257(9) . ? Cl1 C34 1.695(15) . ? Cl2 C34 1.684(13) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? I1 I2 2.9339(9) 2_666 ? 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 P1 N1 90.3(3) . . ? C2 N2 C13 122.9(5) . . ? C2 N2 P1 112.7(4) . . ? C13 N2 P1 124.1(4) . . ? C13 C18 C17 116.1(6) . . ? C13 C18 C19 123.9(6) . . ? C17 C18 C19 120.1(6) . . ? C1 N1 C33 126.9(5) . . ? C1 N1 P1 113.3(4) . . ? C33 N1 P1 119.7(4) . . ? C30 C31 C32 118.9(7) . . ? C30 C31 H31A 120.5 . . ? C32 C31 H31A 120.5 . . ? C21 N3 C25 119.4(6) . . ? N2 C2 C1 112.3(5) . . ? N2 C2 C3 137.1(6) . . ? C1 C2 C3 110.5(5) . . ? C5 C6 C7 120.5(6) . . ? C5 C6 H6A 119.8 . . ? C7 C6 H6A 119.8 . . ? C14 C13 C18 123.0(6) . . ? C14 C13 N2 118.2(6) . . ? C18 C13 N2 118.8(5) . . ? C11 C12 C8 119.4(6) . . ? C11 C12 C1 137.3(6) . . ? C8 C12 C1 103.3(5) . . ? C16 C17 C18 122.0(6) . . ? C16 C17 H17A 119.0 . . ? C18 C17 H17A 119.0 . . ? C4 C3 C8 120.0(6) . . ? C4 C3 C2 136.6(6) . . ? C8 C3 C2 103.4(5) . . ? C33 C32 C31 119.4(6) . . ? C33 C32 H32A 120.3 . . ? C31 C32 H32A 120.3 . . ? C32 C33 C28 122.8(6) . . ? C32 C33 N1 117.1(6) . . ? C28 C33 N1 119.9(6) . . ? N1 C1 C2 111.4(5) . . ? N1 C1 C12 139.3(6) . . ? C2 C1 C12 109.3(5) . . ? C15 C14 C13 118.6(7) . . ? C15 C14 H14A 120.7 . . ? C13 C14 H14A 120.7 . . ? C10 C9 C7 120.6(6) . . ? C10 C9 H9A 119.7 . . ? C7 C9 H9A 119.7 . . ? C7 C8 C12 123.3(6) . . ? C7 C8 C3 123.2(6) . . ? C12 C8 C3 113.5(5) . . ? C29 C28 C33 115.9(6) . . ? C29 C28 C27 119.5(6) . . ? C33 C28 C27 124.6(6) . . ? C3 C4 C5 117.1(6) . . ? C3 C4 H4A 121.5 . . ? C5 C4 H4A 121.5 . . ? C28 C27 C26 113.3(6) . . ? C28 C27 H27A 108.9 . . ? C26 C27 H27A 108.9 . . ? C28 C27 H27B 108.9 . . ? C26 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? C16 C15 C14 120.3(7) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C12 C11 C10 118.0(6) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? C8 C7 C6 116.3(6) . . ? C8 C7 C9 116.2(6) . . ? C6 C7 C9 127.5(6) . . ? C18 C19 C20 113.6(6) . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19B 108.8 . . ? C20 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? N3 C25 C24 121.8(7) . . ? N3 C25 C26 116.2(7) . . ? C24 C25 C26 122.1(7) . . ? C31 C30 C29 120.8(7) . . ? C31 C30 H30A 119.6 . . ? C29 C30 H30A 119.6 . . ? N3 C21 C22 121.6(7) . . ? N3 C21 C20 116.1(7) . . ? C22 C21 C20 122.2(7) . . ? C30 C29 C28 122.1(7) . . ? C30 C29 H29A 119.0 . . ? C28 C29 H29A 119.0 . . ? C15 C16 C17 120.1(7) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C6 C5 C4 123.0(6) . . ? C6 C5 H5A 118.5 . . ? C4 C5 H5A 118.5 . . ? C21 C20 C19 114.4(6) . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C9 C10 C11 122.4(6) . . ? C9 C10 H10A 118.8 . . ? C11 C10 H10A 118.8 . . ? C25 C26 C27 112.8(6) . . ? C25 C26 H26A 109.0 . . ? C27 C26 H26A 109.0 . . ? C25 C26 H26B 109.0 . . ? C27 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C25 C24 C23 118.5(8) . . ? C25 C24 H24A 120.7 . . ? C23 C24 H24A 120.7 . . ? C22 C23 C24 119.4(8) . . ? C22 C23 H23A 120.3 . . ? C24 C23 H23A 120.3 . . ? C23 C22 C21 119.2(8) . . ? C23 C22 H22A 120.4 . . ? C21 C22 H22A 120.4 . . ? I4 I3 I4 180.0 2_557 . ? Cl2 C34 Cl1 116.3(9) . . ? Cl2 C34 H34A 108.2 . . ? Cl1 C34 H34A 108.2 . . ? Cl2 C34 H34B 108.2 . . ? Cl1 C34 H34B 108.2 . . ? H34A C34 H34B 107.4 . . ? I2 I1 I2 180.0 2_666 . ? 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 N1 P1 N2 C2 -0.2(4) . . . . ? N1 P1 N2 C13 -175.0(5) . . . . ? N2 P1 N1 C1 0.5(4) . . . . ? N2 P1 N1 C33 176.7(5) . . . . ? C13 N2 C2 C1 174.7(5) . . . . ? P1 N2 C2 C1 -0.2(6) . . . . ? C13 N2 C2 C3 -2.3(11) . . . . ? P1 N2 C2 C3 -177.2(6) . . . . ? C17 C18 C13 C14 0.0(9) . . . . ? C19 C18 C13 C14 -179.4(6) . . . . ? C17 C18 C13 N2 179.4(5) . . . . ? C19 C18 C13 N2 0.0(9) . . . . ? C2 N2 C13 C14 108.5(7) . . . . ? P1 N2 C13 C14 -77.2(7) . . . . ? C2 N2 C13 C18 -71.0(8) . . . . ? P1 N2 C13 C18 103.3(6) . . . . ? C13 C18 C17 C16 0.6(9) . . . . ? C19 C18 C17 C16 180.0(6) . . . . ? N2 C2 C3 C4 -1.6(13) . . . . ? C1 C2 C3 C4 -178.7(7) . . . . ? N2 C2 C3 C8 177.6(7) . . . . ? C1 C2 C3 C8 0.5(6) . . . . ? C30 C31 C32 C33 0.3(10) . . . . ? C31 C32 C33 C28 -0.8(10) . . . . ? C31 C32 C33 N1 -176.4(6) . . . . ? C1 N1 C33 C32 -121.4(7) . . . . ? P1 N1 C33 C32 62.9(7) . . . . ? C1 N1 C33 C28 63.0(8) . . . . ? P1 N1 C33 C28 -112.7(6) . . . . ? C33 N1 C1 C2 -176.6(5) . . . . ? P1 N1 C1 C2 -0.6(6) . . . . ? C33 N1 C1 C12 2.8(11) . . . . ? P1 N1 C1 C12 178.8(6) . . . . ? N2 C2 C1 N1 0.5(7) . . . . ? C3 C2 C1 N1 178.3(5) . . . . ? N2 C2 C1 C12 -179.1(5) . . . . ? C3 C2 C1 C12 -1.2(7) . . . . ? C11 C12 C1 N1 0.9(13) . . . . ? C8 C12 C1 N1 -177.9(7) . . . . ? C11 C12 C1 C2 -179.7(7) . . . . ? C8 C12 C1 C2 1.5(6) . . . . ? C18 C13 C14 C15 -0.1(10) . . . . ? N2 C13 C14 C15 -179.6(6) . . . . ? C11 C12 C8 C7 -1.3(9) . . . . ? C1 C12 C8 C7 177.8(5) . . . . ? C11 C12 C8 C3 179.7(5) . . . . ? C1 C12 C8 C3 -1.2(7) . . . . ? C4 C3 C8 C7 0.9(9) . . . . ? C2 C3 C8 C7 -178.5(6) . . . . ? C4 C3 C8 C12 179.9(6) . . . . ? C2 C3 C8 C12 0.5(7) . . . . ? C32 C33 C28 C29 0.7(9) . . . . ? N1 C33 C28 C29 176.1(5) . . . . ? C32 C33 C28 C27 -176.9(6) . . . . ? N1 C33 C28 C27 -1.5(9) . . . . ? C8 C3 C4 C5 -1.2(9) . . . . ? C2 C3 C4 C5 177.9(7) . . . . ? C29 C28 C27 C26 -72.8(8) . . . . ? C33 C28 C27 C26 104.7(7) . . . . ? C13 C14 C15 C16 -0.2(10) . . . . ? C8 C12 C11 C10 1.0(9) . . . . ? C1 C12 C11 C10 -177.7(7) . . . . ? C12 C8 C7 C6 -178.9(6) . . . . ? C3 C8 C7 C6 -0.1(9) . . . . ? C12 C8 C7 C9 0.9(9) . . . . ? C3 C8 C7 C9 179.8(6) . . . . ? C5 C6 C7 C8 -0.3(9) . . . . ? C5 C6 C7 C9 179.8(6) . . . . ? C10 C9 C7 C8 -0.3(9) . . . . ? C10 C9 C7 C6 179.5(7) . . . . ? C13 C18 C19 C20 -102.6(7) . . . . ? C17 C18 C19 C20 78.1(8) . . . . ? C21 N3 C25 C24 3.2(10) . . . . ? C21 N3 C25 C26 -176.5(6) . . . . ? C32 C31 C30 C29 0.4(10) . . . . ? C25 N3 C21 C22 -1.9(10) . . . . ? C25 N3 C21 C20 176.4(6) . . . . ? C31 C30 C29 C28 -0.5(11) . . . . ? C33 C28 C29 C30 0.0(9) . . . . ? C27 C28 C29 C30 177.7(6) . . . . ? C14 C15 C16 C17 0.8(11) . . . . ? C18 C17 C16 C15 -0.9(11) . . . . ? C7 C6 C5 C4 -0.1(10) . . . . ? C3 C4 C5 C6 0.9(10) . . . . ? N3 C21 C20 C19 62.5(9) . . . . ? C22 C21 C20 C19 -119.2(8) . . . . ? C18 C19 C20 C21 88.4(8) . . . . ? C7 C9 C10 C11 0.1(10) . . . . ? C12 C11 C10 C9 -0.4(10) . . . . ? N3 C25 C26 C27 -75.8(8) . . . . ? C24 C25 C26 C27 104.6(8) . . . . ? C28 C27 C26 C25 -69.8(8) . . . . ? N3 C25 C24 C23 -2.4(11) . . . . ? C26 C25 C24 C23 177.2(7) . . . . ? C25 C24 C23 C22 0.4(13) . . . . ? C24 C23 C22 C21 0.8(13) . . . . ? N3 C21 C22 C23 -0.1(12) . . . . ? C20 C21 C22 C23 -178.2(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.251 _refine_diff_density_min -1.771 _refine_diff_density_rms 0.191