# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Feihe Huang' _publ_contact_author_email FHUANG@ZJU.EDU.CN _publ_section_title ; Three-Dimensional Bis(m-phenylene)-32-crown-10-Based Cryptand/Paraquat Catenanes ; loop_ _publ_author_name 'Feihe Huang' 'Frank R. Fronczek' 'Menglong Hu' 'Shijun Li' 'Ning Li' 'Ming Liu' 'Feng Wang' 'Mingming Zhang' ; Q.Zhou ; # Attachment 'B815929G-S2.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 701929' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(m-phenylene)-32-crown-10-Based Cryptand/Paraquat [2]Catenane ; _chemical_name_common ;Bis(m-phenylene)-32-crown-10-Based Cryptand/Paraquat (2)Catenane ; _chemical_melting_point 525(2) _chemical_formula_moiety 'C36 H53.925 I0.075 O15, C36 H32 N4, 4(F6 P), 5(C2 H3 N), H2 O' _chemical_formula_sum 'C82 H102.925 F24 I0.075 N9 O16 P4' _chemical_formula_weight 2060.06 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' F F 0.0171 0.0103 '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' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.9005(15) _cell_length_b 14.0323(11) _cell_length_c 26.137(2) _cell_angle_alpha 75.665(4) _cell_angle_beta 81.887(4) _cell_angle_gamma 74.949(5) _cell_volume 4753.9(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 37989 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.8 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2132.0 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KappaCCD (with Oxford Cryostream)' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2 _diffrn_reflns_number 30619 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.24 _reflns_number_total 17056 _reflns_number_gt 12674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR-92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1437P)^2^+15.6290P] 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 17056 _refine_ls_number_parameters 1250 _refine_ls_number_restraints 141 _refine_ls_R_factor_all 0.1168 _refine_ls_R_factor_gt 0.0927 _refine_ls_wR_factor_ref 0.2700 _refine_ls_wR_factor_gt 0.2500 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C11 C 0.1228(3) 0.5015(3) 0.24484(17) 0.0232(9) Uani 1 1 d . . . C12 C 0.1972(3) 0.4808(3) 0.20459(17) 0.0227(9) Uani 1 1 d . . . H12 H 0.1809 0.4873 0.1704 0.027 Uiso 1 1 calc R . . C13 C 0.2962(3) 0.4501(3) 0.21704(17) 0.0238(9) Uani 1 1 d . . . C14 C 0.3230(3) 0.4413(3) 0.26798(17) 0.0245(9) Uani 1 1 d . . . H14 H 0.3895 0.4210 0.2758 0.029 Uiso 1 1 calc R . . C15 C 0.2456(3) 0.4643(3) 0.30675(16) 0.0237(9) Uani 1 1 d . . . C16 C 0.1466(3) 0.4948(3) 0.29594(17) 0.0242(9) Uani 1 1 d . . . H16 H 0.0965 0.5106 0.3222 0.029 Uiso 1 1 calc R . . C21 C 0.0863(3) 1.0120(3) 0.25352(19) 0.0293(10) Uani 1 1 d . B . C22 C 0.1351(4) 1.0063(3) 0.20322(18) 0.0286(10) Uani 1 1 d DU . . H22 H 0.0992 1.0164 0.1741 0.034 Uiso 0.99 1 calc PR A 1 I1 I 0.028(2) 1.044(2) 0.1474(11) 0.044(8) Uani 0.01 1 d PDU B 2 C23 C 0.2390(4) 0.9849(3) 0.19854(18) 0.0278(10) Uani 1 1 d . B . C24 C 0.2917(4) 0.9681(3) 0.24207(18) 0.0287(10) Uani 1 1 d DU . . H24A H 0.3612 0.9520 0.2383 0.034 Uiso 0.96 1 calc PR B 1 I2 I 0.4353(6) 0.9524(7) 0.2266(4) 0.053(2) Uani 0.04 1 d PDU B 2 C25 C 0.2429(4) 0.9750(3) 0.29093(18) 0.0287(10) Uani 1 1 d . B . C26 C 0.1399(4) 0.9972(3) 0.29658(18) 0.0315(10) Uani 1 1 d DU . . H26A H 0.1063 1.0021 0.3296 0.038 Uiso 0.97 1 calc PR B 1 I3 I 0.0867(11) 0.9929(9) 0.3742(4) 0.038(3) Uani 0.03 1 d PDU B 2 O31 O 0.0231(2) 0.5293(2) 0.23797(12) 0.0275(7) Uani 1 1 d . . . C31 C -0.0070(3) 0.5488(3) 0.18528(18) 0.0289(10) Uani 1 1 d . . . H31A H 0.0153 0.4881 0.1713 0.035 Uiso 1 1 calc R . . H31B H 0.0218 0.6016 0.1620 0.035 Uiso 1 1 calc R . . C32 C -0.1189(4) 0.5815(4) 0.1888(2) 0.0327(11) Uani 1 1 d . . . H32A H -0.1427 0.5887 0.1546 0.039 Uiso 1 1 calc R . . H32B H -0.1471 0.5307 0.2143 0.039 Uiso 1 1 calc R . . O32 O -0.1499(2) 0.6745(2) 0.20450(13) 0.0317(7) Uani 1 1 d . . . C33 C -0.2557(4) 0.7061(4) 0.2095(2) 0.0402(12) Uani 1 1 d . . . H33A H -0.2831 0.6541 0.2344 0.048 Uiso 1 1 calc R . . H33B H -0.2815 0.7165 0.1755 0.048 Uiso 1 1 calc R . . C34 C -0.2870(4) 0.8028(4) 0.2288(2) 0.0385(12) Uani 1 1 d . . . H34A H -0.2536 0.8527 0.2062 0.046 Uiso 1 1 calc R . . H34B H -0.3585 0.8294 0.2274 0.046 Uiso 1 1 calc R . . O33 O -0.2615(2) 0.7837(3) 0.28181(13) 0.0357(8) Uani 1 1 d . . . C35 C -0.3145(4) 0.8602(5) 0.3092(2) 0.0464(14) Uani 1 1 d . . . H35A H -0.2928 0.8420 0.3447 0.056 Uiso 1 1 calc R . . H35B H -0.3851 0.8609 0.3124 0.056 Uiso 1 1 calc R . . C36 C -0.3024(4) 0.9648(4) 0.2840(2) 0.0427(13) Uani 1 1 d . . . H36A H -0.3314 0.9878 0.2502 0.051 Uiso 1 1 calc R . . H36B H -0.3371 1.0107 0.3065 0.051 Uiso 1 1 calc R . . O34 O -0.1981(3) 0.9648(3) 0.27637(19) 0.0499(10) Uani 1 1 d . . . C37 C -0.1818(5) 1.0617(5) 0.2444(3) 0.0597(17) Uani 1 1 d . . . H37A H -0.1984 1.1117 0.2661 0.072 Uiso 1 1 calc R . . H37B H -0.2250 1.0854 0.2155 0.072 Uiso 1 1 calc R . . C38 C -0.0745(5) 1.0498(5) 0.2225(3) 0.0535(15) Uani 1 1 d . B . H38A H -0.0551 0.9936 0.2048 0.064 Uiso 1 1 calc R . . H38B H -0.0664 1.1107 0.1967 0.064 Uiso 1 1 calc R . . O35 O -0.0151(3) 1.0323(3) 0.26293(16) 0.0458(9) Uani 1 1 d . . . O41 O 0.3651(2) 0.4289(2) 0.17578(11) 0.0258(7) Uani 1 1 d . . . C41 C 0.4653(3) 0.3751(3) 0.18751(18) 0.0277(10) Uani 1 1 d . . . H41A H 0.4944 0.3371 0.1605 0.033 Uiso 1 1 calc R . . H41B H 0.4626 0.3268 0.2211 0.033 Uiso 1 1 calc R . . C42 C 0.5326(4) 0.4420(3) 0.19040(17) 0.0278(10) Uani 1 1 d . . . H42A H 0.5004 0.4870 0.2138 0.033 Uiso 1 1 calc R . . H42B H 0.5946 0.4007 0.2046 0.033 Uiso 1 1 calc R . . O42 O 0.5530(2) 0.5000(2) 0.13854(11) 0.0242(6) Uani 1 1 d . . . C43 C 0.6246(3) 0.5573(3) 0.13894(18) 0.0273(10) Uani 1 1 d . . . H43A H 0.6859 0.5125 0.1524 0.033 Uiso 1 1 calc R . . H43B H 0.5983 0.6050 0.1616 0.033 Uiso 1 1 calc R . . C44 C 0.6450(3) 0.6131(3) 0.08290(18) 0.0287(10) Uani 1 1 d . . . H44A H 0.7038 0.6394 0.0810 0.034 Uiso 1 1 calc R . . H44B H 0.6598 0.5657 0.0598 0.034 Uiso 1 1 calc R . . O43 O 0.5640(2) 0.6944(2) 0.06416(12) 0.0283(7) Uani 1 1 d . . . C45 C 0.5692(4) 0.7866(4) 0.0758(2) 0.0365(11) Uani 1 1 d . . . H45A H 0.6355 0.7984 0.0646 0.044 Uiso 1 1 calc R . . H45B H 0.5578 0.7816 0.1138 0.044 Uiso 1 1 calc R . . C46 C 0.4928(4) 0.8738(4) 0.0482(2) 0.0348(11) Uani 1 1 d . . . H46A H 0.5105 0.9367 0.0473 0.042 Uiso 1 1 calc R . . H46B H 0.4928 0.8684 0.0119 0.042 Uiso 1 1 calc R . . O44 O 0.3957(2) 0.8754(2) 0.07425(13) 0.0304(7) Uani 1 1 d . . . C47 C 0.3286(4) 0.9724(3) 0.06153(18) 0.0306(10) Uani 1 1 d . . . H47A H 0.2988 0.9793 0.0290 0.037 Uiso 1 1 calc R . . H47B H 0.3651 1.0249 0.0560 0.037 Uiso 1 1 calc R . . C48 C 0.2485(4) 0.9844(3) 0.10561(18) 0.0291(10) Uani 1 1 d . B . H48A H 0.2002 1.0484 0.0962 0.035 Uiso 1 1 calc R . . H48B H 0.2139 0.9301 0.1126 0.035 Uiso 1 1 calc R . . O45 O 0.2957(2) 0.9814(3) 0.15151(12) 0.0315(7) Uani 1 1 d . . . O51 O 0.2643(2) 0.4554(2) 0.35858(12) 0.0289(7) Uani 1 1 d . . . C51 C 0.3666(3) 0.4329(4) 0.36986(18) 0.0289(10) Uani 1 1 d . . . H51A H 0.3960 0.4892 0.3520 0.035 Uiso 1 1 calc R . . H51B H 0.4038 0.3735 0.3569 0.035 Uiso 1 1 calc R . . C52 C 0.3724(4) 0.4140(4) 0.42785(19) 0.0363(11) Uani 1 1 d . . . H52A H 0.3355 0.3636 0.4458 0.044 Uiso 1 1 calc R . . H52B H 0.4416 0.3876 0.4359 0.044 Uiso 1 1 calc R . . O52 O 0.3325(3) 0.5043(3) 0.44662(13) 0.0403(9) Uani 1 1 d . . . C53 C 0.3453(5) 0.4855(4) 0.5025(2) 0.0484(14) Uani 1 1 d . . . H53A H 0.4151 0.4564 0.5087 0.058 Uiso 1 1 calc R . . H53B H 0.3066 0.4382 0.5226 0.058 Uiso 1 1 calc R . . C54 C 0.3115(5) 0.5820(5) 0.5196(2) 0.0517(15) Uani 1 1 d . . . H54A H 0.2442 0.6150 0.5096 0.062 Uiso 1 1 calc R . . H54B H 0.3108 0.5699 0.5578 0.062 Uiso 1 1 calc R . . O53 O 0.3786(3) 0.6451(3) 0.49471(14) 0.0452(9) Uani 1 1 d . . . C55 C 0.3471(5) 0.7398(4) 0.5093(2) 0.0510(15) Uani 1 1 d . . . H55A H 0.3559 0.7311 0.5465 0.061 Uiso 1 1 calc R . . H55B H 0.2769 0.7681 0.5040 0.061 Uiso 1 1 calc R . . C56 C 0.4077(5) 0.8094(4) 0.4762(2) 0.0482(14) Uani 1 1 d . . . H56A H 0.3938 0.8712 0.4891 0.058 Uiso 1 1 calc R . . H56B H 0.4784 0.7776 0.4783 0.058 Uiso 1 1 calc R . . O54 O 0.3830(3) 0.8324(3) 0.42259(14) 0.0431(9) Uani 1 1 d . . . C57 C 0.4225(4) 0.9129(4) 0.3906(2) 0.0408(12) Uani 1 1 d . . . H57A H 0.4946 0.8964 0.3911 0.049 Uiso 1 1 calc R . . H57B H 0.3950 0.9741 0.4038 0.049 Uiso 1 1 calc R . . C58 C 0.3945(4) 0.9284(4) 0.3351(2) 0.0383(12) Uani 1 1 d . B . H58A H 0.4266 0.9779 0.3111 0.046 Uiso 1 1 calc R . . H58B H 0.4159 0.8653 0.3233 0.046 Uiso 1 1 calc R . . O55 O 0.2885(3) 0.9634(2) 0.33566(13) 0.0336(7) Uani 1 1 d . . . C61 C 0.3058(3) 0.3577(3) 0.05542(17) 0.0256(9) Uani 1 1 d . . . C62 C 0.4000(3) 0.3704(3) 0.05929(16) 0.0258(9) Uani 1 1 d . . . H62 H 0.4524 0.3139 0.0674 0.031 Uiso 1 1 calc R . . C63 C 0.4169(3) 0.4662(3) 0.05118(16) 0.0259(9) Uani 1 1 d . . . H63 H 0.4797 0.4738 0.0552 0.031 Uiso 1 1 calc R . . C64 C 0.3398(3) 0.5511(3) 0.03707(16) 0.0252(9) Uani 1 1 d . . . C65 C 0.2466(3) 0.5379(3) 0.03029(18) 0.0265(9) Uani 1 1 d . . . H65 H 0.1956 0.5942 0.0192 0.032 Uiso 1 1 calc R . . C66 C 0.2293(3) 0.4421(3) 0.03985(17) 0.0266(9) Uani 1 1 d . . . H66 H 0.1665 0.4342 0.0359 0.032 Uiso 1 1 calc R . . C67 C 0.2842(4) 0.2540(3) 0.07178(18) 0.0296(10) Uani 1 1 d . . . H67A H 0.2362 0.2489 0.0496 0.035 Uiso 1 1 calc R . . H67B H 0.3451 0.2028 0.0677 0.035 Uiso 1 1 calc R . . C68 C 0.3538(4) 0.6555(4) 0.03385(18) 0.0308(10) Uani 1 1 d . . . H68A H 0.4243 0.6535 0.0327 0.037 Uiso 1 1 calc R . . H68B H 0.3276 0.7013 0.0019 0.037 Uiso 1 1 calc R . . C71 C -0.0124(3) 0.4344(4) 0.42580(18) 0.0307(10) Uani 1 1 d . . . C72 C 0.0581(4) 0.4783(4) 0.43841(18) 0.0340(11) Uani 1 1 d . . . H72 H 0.1119 0.4375 0.4569 0.041 Uiso 1 1 calc R . . C73 C 0.0484(4) 0.5820(4) 0.42356(19) 0.0342(11) Uani 1 1 d . . . H73 H 0.0955 0.6105 0.4323 0.041 Uiso 1 1 calc R . . C74 C -0.0321(4) 0.6438(4) 0.39541(19) 0.0346(11) Uani 1 1 d . . . C75 C -0.1040(4) 0.6007(4) 0.3847(2) 0.0395(12) Uani 1 1 d . . . H75 H -0.1591 0.6419 0.3673 0.047 Uiso 1 1 calc R . . C76 C -0.0949(4) 0.4975(4) 0.3996(2) 0.0397(12) Uani 1 1 d . . . H76 H -0.1438 0.4696 0.3922 0.048 Uiso 1 1 calc R . . C77 C 0.0044(4) 0.3212(4) 0.4356(2) 0.0366(11) Uani 1 1 d . . . H77A H 0.0502 0.2890 0.4630 0.044 Uiso 1 1 calc R . . H77B H -0.0584 0.3015 0.4475 0.044 Uiso 1 1 calc R . . C78 C -0.0352(4) 0.7546(4) 0.3724(2) 0.0385(12) Uani 1 1 d . . . H78A H -0.1039 0.7929 0.3691 0.046 Uiso 1 1 calc R . . H78B H -0.0053 0.7814 0.3955 0.046 Uiso 1 1 calc R . . C80 C 0.1675(3) 0.2378(3) 0.23220(18) 0.0251(9) Uani 1 1 d . . . C81 C 0.2702(3) 0.2099(3) 0.21929(18) 0.0265(9) Uani 1 1 d . . . H81 H 0.3144 0.1905 0.2457 0.032 Uiso 1 1 calc R . . C82 C 0.3061(3) 0.2112(3) 0.16701(18) 0.0275(10) Uani 1 1 d . . . H82 H 0.3747 0.1932 0.1584 0.033 Uiso 1 1 calc R . . N81 N 0.2431(3) 0.2383(3) 0.12836(15) 0.0264(8) Uani 1 1 d . . . C83 C 0.1437(4) 0.2614(3) 0.1403(2) 0.0314(10) Uani 1 1 d . . . H83 H 0.1009 0.2779 0.1135 0.038 Uiso 1 1 calc R . . C84 C 0.1048(4) 0.2608(3) 0.19169(19) 0.0306(10) Uani 1 1 d . . . H84 H 0.0359 0.2761 0.1994 0.037 Uiso 1 1 calc R . . C85 C 0.1261(3) 0.2480(3) 0.28703(19) 0.0259(9) Uani 1 1 d . . . C86 C 0.1869(3) 0.2380(4) 0.32624(19) 0.0308(10) Uani 1 1 d . . . H86 H 0.2559 0.2172 0.3198 0.037 Uiso 1 1 calc R . . C87 C 0.1469(4) 0.2586(4) 0.37523(19) 0.0326(11) Uani 1 1 d . . . H87 H 0.1889 0.2523 0.4012 0.039 Uiso 1 1 calc R . . N82 N 0.0474(3) 0.2876(3) 0.38508(16) 0.0325(9) Uani 1 1 d . . . C88 C -0.0139(4) 0.2938(5) 0.3487(2) 0.0476(14) Uani 1 1 d . . . H88 H -0.0826 0.3110 0.3568 0.057 Uiso 1 1 calc R . . C89 C 0.0226(4) 0.2754(5) 0.2994(2) 0.0458(14) Uani 1 1 d . . . H89 H -0.0213 0.2810 0.2744 0.055 Uiso 1 1 calc R . . C90 C 0.1931(3) 0.7363(3) 0.17356(18) 0.0249(9) Uani 1 1 d . . . C91 C 0.2953(3) 0.6936(3) 0.17203(18) 0.0259(9) Uani 1 1 d . . . H91 H 0.3290 0.6800 0.2023 0.031 Uiso 1 1 calc R . . C92 C 0.3467(3) 0.6713(3) 0.12580(18) 0.0272(10) Uani 1 1 d . . . H92 H 0.4148 0.6417 0.1252 0.033 Uiso 1 1 calc R . . N91 N 0.2993(3) 0.6920(3) 0.08170(15) 0.0261(8) Uani 1 1 d . . . C93 C 0.2011(4) 0.7384(3) 0.08118(19) 0.0304(10) Uani 1 1 d . . . H93 H 0.1702 0.7552 0.0498 0.036 Uiso 1 1 calc R . . C94 C 0.1467(3) 0.7609(3) 0.1262(2) 0.0299(10) Uani 1 1 d . . . H94 H 0.0790 0.7923 0.1255 0.036 Uiso 1 1 calc R . . C95 C 0.1335(3) 0.7518(3) 0.22402(19) 0.0271(10) Uani 1 1 d . . . C96 C 0.1785(3) 0.7503(3) 0.26890(19) 0.0267(10) Uani 1 1 d . . . H96 H 0.2470 0.7451 0.2669 0.032 Uiso 1 1 calc R . . C97 C 0.1220(3) 0.7565(3) 0.3158(2) 0.0307(10) Uani 1 1 d . . . H97 H 0.1521 0.7559 0.3455 0.037 Uiso 1 1 calc R . . N92 N 0.0220(3) 0.7634(3) 0.31900(17) 0.0322(9) Uani 1 1 d . . . C98 C -0.0233(4) 0.7670(4) 0.2767(2) 0.0338(11) Uani 1 1 d . . . H98 H -0.0920 0.7731 0.2797 0.041 Uiso 1 1 calc R . . C99 C 0.0301(3) 0.7618(3) 0.2289(2) 0.0304(10) Uani 1 1 d . . . H99 H -0.0024 0.7650 0.1995 0.037 Uiso 1 1 calc R . . P1 P 0.69745(11) 0.35413(12) 0.31812(6) 0.0431(4) Uani 1 1 d D . . F11 F 0.7419(3) 0.2524(3) 0.35912(16) 0.0770(12) Uani 1 1 d D . . F12 F 0.6028(3) 0.3789(3) 0.35972(14) 0.0583(9) Uani 1 1 d D . . F13 F 0.6405(3) 0.2941(3) 0.29323(14) 0.0579(9) Uani 1 1 d D . . F14 F 0.6549(3) 0.4573(3) 0.27781(13) 0.0605(10) Uani 1 1 d D . . F15 F 0.7932(3) 0.3294(4) 0.27806(19) 0.0865(14) Uani 1 1 d D . . F16 F 0.7549(3) 0.4132(3) 0.34431(16) 0.0678(11) Uani 1 1 d D . . P2 P 0.60390(10) 1.07684(9) 0.11681(5) 0.0326(3) Uani 1 1 d D . . F21 F 0.4965(2) 1.1015(2) 0.09360(12) 0.0433(7) Uani 1 1 d D . . F22 F 0.5602(3) 1.1643(4) 0.1481(2) 0.0860(15) Uani 1 1 d D . . F23 F 0.5663(3) 1.0000(4) 0.16597(18) 0.0866(15) Uani 1 1 d D . . F24 F 0.7096(2) 1.0542(2) 0.14032(13) 0.0462(8) Uani 1 1 d D . . F25 F 0.6447(3) 0.9881(3) 0.0867(2) 0.0827(15) Uani 1 1 d D . . F26 F 0.6376(3) 1.1560(3) 0.06766(18) 0.0844(15) Uani 1 1 d D . . P3 P 0.95725(9) 0.72970(10) 0.01501(5) 0.0338(3) Uani 1 1 d D . . F31 F 0.9595(3) 0.7958(3) 0.05563(19) 0.0865(15) Uani 1 1 d D . . F32 F 1.0643(2) 0.7505(3) -0.01258(13) 0.0532(9) Uani 1 1 d D . . F33 F 0.9008(3) 0.8254(3) -0.02511(17) 0.0692(11) Uani 1 1 d D . . F34 F 0.9611(3) 0.6617(3) -0.02586(14) 0.0545(9) Uani 1 1 d D . . F35 F 0.8535(2) 0.7087(4) 0.04052(16) 0.0734(12) Uani 1 1 d D . . F36 F 1.0159(2) 0.6329(2) 0.05512(12) 0.0469(8) Uani 1 1 d D . . P4 P 0.28666(14) 0.14241(12) 0.51854(6) 0.0595(5) Uani 1 1 d DU . . F41 F 0.1713(3) 0.1770(5) 0.5174(2) 0.244(5) Uani 1 1 d DU . . F42 F 0.3050(3) 0.1808(4) 0.45673(15) 0.121(2) Uani 1 1 d DU . . F43 F 0.2907(6) 0.2482(4) 0.5262(2) 0.391(8) Uani 1 1 d DU . . F44 F 0.4036(4) 0.1068(6) 0.5198(2) 0.219(4) Uani 1 1 d DU . . F45 F 0.2697(4) 0.1035(4) 0.58075(16) 0.162(3) Uani 1 1 d DU . . F46 F 0.2832(5) 0.0375(4) 0.5111(2) 0.168(3) Uani 1 1 d DU . . N1 N 0.8895(4) 0.3534(5) 0.1505(3) 0.0727(18) Uani 1 1 d . . . C1 C 0.8332(5) 0.3253(4) 0.1349(3) 0.0490(14) Uani 1 1 d . . . C2 C 0.7579(5) 0.2932(6) 0.1134(3) 0.0646(18) Uani 1 1 d . . . H2A H 0.7059 0.3511 0.1007 0.097 Uiso 1 1 calc R . . H2B H 0.7298 0.2461 0.1408 0.097 Uiso 1 1 calc R . . H2C H 0.7886 0.2612 0.0848 0.097 Uiso 1 1 calc R . . N2 N -0.0057(4) 0.9842(4) 0.1071(2) 0.0568(14) Uani 1 1 d . . . C3 C -0.0608(4) 1.0041(4) 0.0756(2) 0.0420(12) Uani 1 1 d . . . C4 C -0.1306(5) 1.0304(5) 0.0350(3) 0.0528(15) Uani 1 1 d . . . H4A H -0.1597 0.9743 0.0372 0.079 Uiso 1 1 calc R . . H4B H -0.0958 1.0459 0.0007 0.079 Uiso 1 1 calc R . . H4C H -0.1824 1.0882 0.0404 0.079 Uiso 1 1 calc R . . N3A N 0.0965(7) 0.8170(7) 0.4442(4) 0.041(2) Uiso 0.50 1 d P C 1 C5A C 0.1168(10) 0.8934(10) 0.4480(5) 0.059(3) Uiso 0.50 1 d P C 1 C6A C 0.1525(10) 0.9767(10) 0.4527(6) 0.059(3) Uiso 0.50 1 d P C 1 H6A H 0.1010 1.0205 0.4703 0.089 Uiso 0.50 1 calc PR C 1 H6B H 0.1708 1.0134 0.4181 0.089 Uiso 0.50 1 calc PR C 1 H6C H 0.2099 0.9523 0.4730 0.089 Uiso 0.50 1 calc PR C 1 N3B N -0.0793(13) 1.1163(14) 0.4418(7) 0.106(5) Uiso 0.50 1 d P D 2 C5B C -0.0973(11) 1.0833(12) 0.4167(6) 0.065(4) Uiso 0.50 1 d P D 2 C6B C -0.1237(10) 1.0296(10) 0.3859(5) 0.055(3) Uiso 0.50 1 d P D 2 H6D H -0.0839 1.0361 0.3526 0.083 Uiso 0.50 1 calc PR D 2 H6E H -0.1931 1.0555 0.3797 0.083 Uiso 0.50 1 calc PR D 2 H6F H -0.1125 0.9595 0.4037 0.083 Uiso 0.50 1 calc PR D 2 N4 N 0.4619(5) 0.6768(4) 0.2611(3) 0.0662(16) Uani 1 1 d . . . C7 C 0.5024(5) 0.6590(4) 0.2979(3) 0.0465(14) Uani 1 1 d . . . C8 C 0.5546(5) 0.6351(5) 0.3462(3) 0.0528(15) Uani 1 1 d . . . H8A H 0.5115 0.6659 0.3726 0.079 Uiso 1 1 calc R . . H8B H 0.6139 0.6608 0.3383 0.079 Uiso 1 1 calc R . . H8C H 0.5725 0.5631 0.3591 0.079 Uiso 1 1 calc R . . N5 N 0.4398(3) 0.1682(3) 0.31446(17) 0.0357(9) Uani 1 1 d . . . C9 C 0.4829(3) 0.1557(3) 0.35053(19) 0.0294(10) Uani 1 1 d . . . C10 C 0.5387(4) 0.1392(4) 0.3966(2) 0.0444(13) Uani 1 1 d . . . H10A H 0.5843 0.1829 0.3887 0.067 Uiso 1 1 calc R . . H10B H 0.5755 0.0700 0.4050 0.067 Uiso 1 1 calc R . . H10C H 0.4930 0.1540 0.4263 0.067 Uiso 1 1 calc R . . O1W O 0.2978(4) 0.7052(4) 0.3819(2) 0.0769(16) Uani 1 1 d . . . H1A H 0.3087 0.6463 0.4018 0.115 Uiso 1 1 d R . . H1B H 0.3217 0.7424 0.3955 0.115 Uiso 1 1 d R . . 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 C11 0.028(2) 0.0167(19) 0.026(2) -0.0033(16) -0.0060(18) -0.0059(17) C12 0.033(2) 0.0164(19) 0.021(2) -0.0016(16) -0.0033(18) -0.0113(17) C13 0.029(2) 0.021(2) 0.023(2) -0.0051(17) -0.0012(18) -0.0090(18) C14 0.029(2) 0.022(2) 0.022(2) -0.0030(17) -0.0036(18) -0.0078(18) C15 0.032(2) 0.021(2) 0.019(2) -0.0016(16) -0.0048(17) -0.0094(18) C16 0.030(2) 0.019(2) 0.021(2) -0.0037(16) 0.0006(18) -0.0050(17) C21 0.029(2) 0.018(2) 0.041(3) -0.0064(19) 0.001(2) -0.0073(18) C22 0.037(3) 0.020(2) 0.029(2) -0.0051(18) -0.005(2) -0.0076(19) I1 0.06(2) 0.024(15) 0.036(17) 0.005(13) -0.013(13) 0.006(14) C23 0.037(3) 0.017(2) 0.029(2) -0.0025(17) 0.001(2) -0.0101(18) C24 0.036(3) 0.023(2) 0.028(2) -0.0047(18) -0.0009(19) -0.0106(19) I2 0.058(5) 0.043(5) 0.060(6) -0.009(4) -0.003(5) -0.019(4) C25 0.038(3) 0.020(2) 0.030(2) -0.0050(18) -0.001(2) -0.0111(19) C26 0.047(3) 0.024(2) 0.027(2) -0.0090(18) 0.003(2) -0.012(2) I3 0.061(9) 0.024(6) 0.033(6) -0.009(5) -0.012(6) -0.008(6) O31 0.0251(16) 0.0312(16) 0.0250(16) -0.0029(13) -0.0055(13) -0.0058(13) C31 0.031(2) 0.027(2) 0.031(2) -0.0061(19) -0.0108(19) -0.0060(19) C32 0.033(3) 0.030(2) 0.038(3) -0.007(2) -0.011(2) -0.009(2) O32 0.0269(17) 0.0301(17) 0.0400(19) -0.0088(14) -0.0109(14) -0.0050(13) C33 0.029(3) 0.040(3) 0.056(3) -0.014(2) -0.019(2) -0.003(2) C34 0.033(3) 0.039(3) 0.045(3) -0.011(2) -0.015(2) -0.002(2) O33 0.0285(18) 0.0422(19) 0.0367(19) -0.0088(15) -0.0063(14) -0.0066(15) C35 0.027(3) 0.069(4) 0.041(3) -0.019(3) 0.004(2) -0.005(3) C36 0.022(2) 0.055(3) 0.057(3) -0.032(3) -0.003(2) 0.001(2) O34 0.0243(18) 0.041(2) 0.091(3) -0.030(2) -0.0100(19) -0.0016(16) C37 0.045(4) 0.046(3) 0.092(5) -0.025(3) -0.023(3) -0.001(3) C38 0.047(3) 0.047(3) 0.070(4) -0.017(3) -0.008(3) -0.011(3) O35 0.032(2) 0.048(2) 0.058(2) -0.0225(19) 0.0029(17) -0.0055(17) O41 0.0265(16) 0.0318(16) 0.0213(15) -0.0062(12) 0.0004(12) -0.0113(13) C41 0.028(2) 0.027(2) 0.028(2) -0.0055(18) -0.0003(18) -0.0069(19) C42 0.031(2) 0.031(2) 0.021(2) -0.0025(18) -0.0030(18) -0.0094(19) O42 0.0245(16) 0.0276(16) 0.0224(15) -0.0025(12) -0.0052(12) -0.0109(13) C43 0.020(2) 0.033(2) 0.031(2) -0.0079(19) -0.0050(18) -0.0074(18) C44 0.023(2) 0.032(2) 0.033(2) -0.0084(19) -0.0009(19) -0.0086(19) O43 0.0304(17) 0.0254(16) 0.0329(17) -0.0064(13) -0.0065(14) -0.0110(13) C45 0.037(3) 0.032(3) 0.048(3) -0.010(2) -0.013(2) -0.015(2) C46 0.037(3) 0.028(2) 0.042(3) -0.004(2) -0.004(2) -0.015(2) O44 0.0391(19) 0.0210(15) 0.0319(17) -0.0036(13) -0.0006(14) -0.0117(14) C47 0.043(3) 0.025(2) 0.025(2) -0.0038(18) -0.005(2) -0.010(2) C48 0.036(3) 0.027(2) 0.028(2) -0.0050(18) -0.0060(19) -0.013(2) O45 0.0355(18) 0.0399(18) 0.0235(16) -0.0083(14) 0.0000(14) -0.0168(15) O51 0.0315(17) 0.0371(18) 0.0182(15) -0.0048(13) -0.0057(13) -0.0075(14) C51 0.031(2) 0.031(2) 0.026(2) -0.0083(19) -0.0076(19) -0.0045(19) C52 0.042(3) 0.039(3) 0.029(3) -0.005(2) -0.011(2) -0.010(2) O52 0.057(2) 0.043(2) 0.0241(17) -0.0098(15) -0.0038(16) -0.0148(17) C53 0.073(4) 0.052(3) 0.023(3) -0.005(2) -0.007(3) -0.022(3) C54 0.059(4) 0.070(4) 0.029(3) -0.011(3) -0.004(3) -0.020(3) O53 0.066(3) 0.041(2) 0.0317(19) -0.0058(16) -0.0147(18) -0.0143(19) C55 0.076(4) 0.049(3) 0.028(3) -0.008(2) -0.019(3) -0.008(3) C56 0.071(4) 0.045(3) 0.036(3) -0.010(2) -0.028(3) -0.012(3) O54 0.071(3) 0.0353(19) 0.0292(18) -0.0060(15) -0.0192(17) -0.0159(18) C57 0.049(3) 0.039(3) 0.037(3) -0.011(2) -0.007(2) -0.011(2) C58 0.047(3) 0.037(3) 0.034(3) -0.009(2) -0.006(2) -0.013(2) O55 0.041(2) 0.0359(18) 0.0265(17) -0.0091(14) -0.0040(14) -0.0098(15) C61 0.031(2) 0.029(2) 0.019(2) -0.0092(17) -0.0028(18) -0.0070(19) C62 0.026(2) 0.033(2) 0.018(2) -0.0074(18) -0.0028(17) -0.0029(18) C63 0.022(2) 0.039(3) 0.018(2) -0.0051(18) 0.0022(17) -0.0115(19) C64 0.028(2) 0.031(2) 0.018(2) -0.0035(17) 0.0008(17) -0.0128(19) C65 0.025(2) 0.025(2) 0.028(2) -0.0051(18) -0.0039(18) -0.0042(18) C66 0.025(2) 0.032(2) 0.026(2) -0.0075(18) -0.0036(18) -0.0106(19) C67 0.037(3) 0.026(2) 0.029(2) -0.0086(19) -0.008(2) -0.008(2) C68 0.032(3) 0.036(3) 0.027(2) -0.0014(19) -0.0026(19) -0.018(2) C71 0.027(2) 0.037(3) 0.024(2) -0.0083(19) 0.0067(18) -0.004(2) C72 0.033(3) 0.046(3) 0.019(2) -0.007(2) 0.0005(19) -0.004(2) C73 0.035(3) 0.043(3) 0.027(2) -0.016(2) 0.002(2) -0.008(2) C74 0.030(3) 0.041(3) 0.032(3) -0.020(2) 0.007(2) -0.002(2) C75 0.025(3) 0.040(3) 0.050(3) -0.011(2) -0.005(2) 0.001(2) C76 0.028(3) 0.046(3) 0.046(3) -0.015(2) 0.001(2) -0.008(2) C77 0.031(3) 0.042(3) 0.032(3) -0.006(2) 0.007(2) -0.007(2) C78 0.035(3) 0.038(3) 0.045(3) -0.022(2) 0.003(2) -0.003(2) C80 0.028(2) 0.0124(19) 0.037(2) -0.0051(17) -0.0046(19) -0.0085(17) C81 0.030(2) 0.022(2) 0.028(2) -0.0052(18) -0.0061(19) -0.0048(18) C82 0.027(2) 0.021(2) 0.034(2) -0.0058(18) -0.0076(19) -0.0007(18) N81 0.032(2) 0.0188(17) 0.032(2) -0.0059(15) -0.0089(16) -0.0080(15) C83 0.032(3) 0.028(2) 0.038(3) -0.003(2) -0.012(2) -0.014(2) C84 0.026(2) 0.029(2) 0.039(3) -0.003(2) -0.005(2) -0.0127(19) C85 0.026(2) 0.017(2) 0.037(3) -0.0063(18) -0.0017(19) -0.0087(17) C86 0.023(2) 0.032(2) 0.035(3) -0.006(2) -0.0017(19) -0.0026(19) C87 0.029(3) 0.034(3) 0.030(2) -0.002(2) -0.001(2) -0.005(2) N82 0.029(2) 0.029(2) 0.037(2) -0.0083(17) 0.0040(17) -0.0057(17) C88 0.027(3) 0.065(4) 0.056(4) -0.032(3) 0.005(2) -0.006(3) C89 0.025(3) 0.059(3) 0.061(4) -0.030(3) -0.008(2) -0.003(2) C90 0.026(2) 0.0148(19) 0.036(2) -0.0011(17) -0.0080(19) -0.0092(17) C91 0.028(2) 0.022(2) 0.028(2) 0.0010(17) -0.0102(18) -0.0095(18) C92 0.024(2) 0.024(2) 0.033(2) -0.0004(18) -0.0066(19) -0.0094(18) N91 0.027(2) 0.0232(18) 0.031(2) -0.0008(15) -0.0057(16) -0.0127(15) C93 0.033(3) 0.024(2) 0.037(3) -0.0012(19) -0.015(2) -0.0106(19) C94 0.025(2) 0.023(2) 0.044(3) -0.007(2) -0.012(2) -0.0050(18) C95 0.027(2) 0.015(2) 0.040(3) -0.0057(18) -0.0084(19) -0.0038(17) C96 0.026(2) 0.017(2) 0.038(3) -0.0060(18) -0.0073(19) -0.0042(17) C97 0.030(3) 0.020(2) 0.045(3) -0.011(2) -0.011(2) -0.0041(18) N92 0.030(2) 0.025(2) 0.041(2) -0.0137(17) -0.0007(18) -0.0017(16) C98 0.025(2) 0.029(2) 0.050(3) -0.013(2) -0.011(2) -0.0009(19) C99 0.027(2) 0.026(2) 0.040(3) -0.011(2) -0.008(2) -0.0029(19) P1 0.0366(8) 0.0608(9) 0.0342(7) -0.0081(6) -0.0107(6) -0.0136(7) F11 0.086(3) 0.069(3) 0.066(3) -0.011(2) -0.042(2) 0.016(2) F12 0.048(2) 0.064(2) 0.054(2) -0.0041(17) 0.0035(16) -0.0098(17) F13 0.076(2) 0.054(2) 0.052(2) 0.0049(16) -0.0278(18) -0.0330(18) F14 0.092(3) 0.061(2) 0.0418(19) 0.0059(16) -0.0256(18) -0.046(2) F15 0.070(3) 0.119(4) 0.090(3) -0.061(3) 0.028(2) -0.038(3) F16 0.048(2) 0.097(3) 0.074(3) -0.042(2) -0.0226(18) -0.013(2) P2 0.0339(7) 0.0251(6) 0.0396(7) -0.0090(5) -0.0125(5) -0.0017(5) F21 0.0367(17) 0.0463(17) 0.0476(18) -0.0116(14) -0.0149(14) -0.0039(13) F22 0.051(2) 0.102(3) 0.132(4) -0.091(3) -0.019(2) 0.003(2) F23 0.053(2) 0.107(3) 0.085(3) 0.038(3) -0.028(2) -0.035(2) F24 0.0345(16) 0.0440(17) 0.062(2) -0.0137(15) -0.0189(15) -0.0035(13) F25 0.042(2) 0.079(3) 0.153(4) -0.084(3) -0.011(2) -0.0041(19) F26 0.061(2) 0.094(3) 0.083(3) 0.039(2) -0.024(2) -0.037(2) P3 0.0280(7) 0.0380(7) 0.0389(7) -0.0098(6) -0.0138(5) -0.0071(5) F31 0.089(3) 0.083(3) 0.098(3) -0.056(3) -0.050(3) 0.017(2) F32 0.0437(19) 0.058(2) 0.055(2) 0.0157(16) -0.0198(15) -0.0259(16) F33 0.070(3) 0.049(2) 0.084(3) 0.0016(19) -0.050(2) -0.0003(18) F34 0.062(2) 0.057(2) 0.052(2) -0.0208(16) -0.0108(17) -0.0155(17) F35 0.0287(18) 0.120(4) 0.066(2) -0.008(2) -0.0021(16) -0.020(2) F36 0.0398(17) 0.0546(19) 0.0382(17) 0.0047(14) -0.0064(13) -0.0091(14) P4 0.0824(13) 0.0493(9) 0.0448(9) -0.0176(7) 0.0024(8) -0.0091(8) F41 0.094(4) 0.336(10) 0.126(5) 0.081(6) 0.023(4) 0.114(5) F42 0.085(3) 0.169(5) 0.055(3) 0.029(3) -0.005(2) 0.010(3) F43 0.706(18) 0.197(7) 0.330(12) -0.191(9) 0.349(14) -0.295(10) F44 0.104(4) 0.457(13) 0.093(5) 0.021(7) -0.032(3) -0.124(6) F45 0.181(6) 0.287(9) 0.048(3) -0.048(4) 0.013(3) -0.112(7) F46 0.246(8) 0.107(4) 0.172(6) -0.086(4) 0.118(6) -0.097(5) N1 0.042(3) 0.071(4) 0.113(5) -0.039(4) -0.034(3) 0.007(3) C1 0.042(3) 0.044(3) 0.058(4) -0.015(3) -0.007(3) -0.001(3) C2 0.066(4) 0.063(4) 0.075(5) -0.019(4) -0.013(4) -0.025(3) N2 0.055(3) 0.054(3) 0.065(3) -0.026(3) -0.020(3) 0.000(2) C3 0.038(3) 0.043(3) 0.046(3) -0.012(2) -0.007(3) -0.008(2) C4 0.049(4) 0.054(4) 0.054(4) -0.010(3) -0.013(3) -0.006(3) N4 0.066(4) 0.059(3) 0.075(4) -0.011(3) -0.034(3) -0.006(3) C7 0.048(3) 0.037(3) 0.057(4) -0.007(3) -0.018(3) -0.012(2) C8 0.053(4) 0.053(4) 0.058(4) -0.007(3) -0.021(3) -0.018(3) N5 0.031(2) 0.037(2) 0.038(2) -0.0069(18) -0.0056(19) -0.0062(18) C9 0.028(2) 0.026(2) 0.032(3) -0.0064(19) 0.000(2) -0.0021(18) C10 0.045(3) 0.050(3) 0.038(3) -0.009(2) -0.012(2) -0.008(3) O1W 0.099(4) 0.060(3) 0.083(4) 0.013(2) -0.063(3) -0.036(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 C11 O31 1.364(5) . ? C11 C16 1.395(6) . ? C11 C12 1.395(6) . ? C12 C13 1.392(6) . ? C12 H12 0.9300 . ? C13 O41 1.374(5) . ? C13 C14 1.401(6) . ? C14 C15 1.401(6) . ? C14 H14 0.9300 . ? C15 C16 1.379(6) . ? C15 O51 1.385(5) . ? C16 H16 0.9300 . ? C21 O35 1.363(6) . ? C21 C26 1.380(7) . ? C21 C22 1.402(7) . ? C22 C23 1.391(7) . ? C22 I1 2.112(10) . ? C22 H22 0.9300 . ? C23 O45 1.368(5) . ? C23 C24 1.379(7) . ? C24 C25 1.372(7) . ? C24 I2 1.945(8) . ? C24 H24A 0.9300 . ? C25 O55 1.363(6) . ? C25 C26 1.379(7) . ? C26 I3 2.051(9) . ? C26 H26A 0.9300 . ? O31 C31 1.437(5) . ? C31 C32 1.499(7) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 O32 1.407(6) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? O32 C33 1.418(6) . ? C33 C34 1.501(7) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 O33 1.422(6) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? O33 C35 1.424(6) . ? C35 C36 1.495(9) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 O34 1.435(6) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? O34 C37 1.464(8) . ? C37 C38 1.502(9) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 O35 1.368(7) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? O41 C41 1.437(5) . ? C41 C42 1.508(6) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 O42 1.430(5) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? O42 C43 1.435(5) . ? C43 C44 1.506(6) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 O43 1.422(5) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? O43 C45 1.422(6) . ? C45 C46 1.500(7) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 O44 1.422(6) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? O44 C47 1.427(6) . ? C47 C48 1.495(7) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 O45 1.434(5) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? O51 C51 1.431(6) . ? C51 C52 1.483(6) . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 O52 1.421(6) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? O52 C53 1.447(6) . ? C53 C54 1.471(8) . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C54 O53 1.431(7) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? O53 C55 1.416(7) . ? C55 C56 1.489(9) . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C56 O54 1.429(6) . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? O54 C57 1.414(7) . ? C57 C58 1.504(7) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C58 O55 1.425(6) . ? C58 H58A 0.9700 . ? C58 H58B 0.9700 . ? C61 C62 1.387(6) . ? C61 C66 1.389(6) . ? C61 C67 1.507(6) . ? C62 C63 1.384(6) . ? C62 H62 0.9300 . ? C63 C64 1.391(6) . ? C63 H63 0.9300 . ? C64 C65 1.395(6) . ? C64 C68 1.509(6) . ? C65 C66 1.384(6) . ? C65 H65 0.9300 . ? C66 H66 0.9300 . ? C67 N81 1.493(6) . ? C67 H67A 0.9700 . ? C67 H67B 0.9700 . ? C68 N91 1.500(6) . ? C68 H68A 0.9700 . ? C68 H68B 0.9700 . ? C71 C72 1.396(7) . ? C71 C76 1.402(7) . ? C71 C77 1.506(7) . ? C72 C73 1.386(7) . ? C72 H72 0.9300 . ? C73 C74 1.400(7) . ? C73 H73 0.9300 . ? C74 C75 1.385(7) . ? C74 C78 1.514(7) . ? C75 C76 1.381(8) . ? C75 H75 0.9300 . ? C76 H76 0.9300 . ? C77 N82 1.504(6) . ? C77 H77A 0.9700 . ? C77 H77B 0.9700 . ? C78 N92 1.500(6) . ? C78 H78A 0.9700 . ? C78 H78B 0.9700 . ? C80 C84 1.388(7) . ? C80 C81 1.395(6) . ? C80 C85 1.494(6) . ? C81 C82 1.384(7) . ? C81 H81 0.9300 . ? C82 N81 1.349(6) . ? C82 H82 0.9300 . ? N81 C83 1.344(6) . ? C83 C84 1.375(7) . ? C83 H83 0.9300 . ? C84 H84 0.9300 . ? C85 C86 1.377(7) . ? C85 C89 1.402(7) . ? C86 C87 1.390(7) . ? C86 H86 0.9300 . ? C87 N82 1.343(6) . ? C87 H87 0.9300 . ? N82 C88 1.337(7) . ? C88 C89 1.377(8) . ? C88 H88 0.9300 . ? C89 H89 0.9300 . ? C90 C91 1.390(6) . ? C90 C94 1.402(6) . ? C90 C95 1.487(7) . ? C91 C92 1.377(7) . ? C91 H91 0.9300 . ? C92 N91 1.340(6) . ? C92 H92 0.9300 . ? N91 C93 1.351(6) . ? C93 C94 1.366(7) . ? C93 H93 0.9300 . ? C94 H94 0.9300 . ? C95 C99 1.398(6) . ? C95 C96 1.399(6) . ? C96 C97 1.367(7) . ? C96 H96 0.9300 . ? C97 N92 1.361(6) . ? C97 H97 0.9300 . ? N92 C98 1.331(6) . ? C98 C99 1.370(7) . ? C98 H98 0.9300 . ? C99 H99 0.9300 . ? P1 F13 1.589(3) . ? P1 F14 1.591(4) . ? P1 F15 1.592(4) . ? P1 F11 1.594(4) . ? P1 F16 1.604(4) . ? P1 F12 1.606(4) . ? P2 F25 1.576(4) . ? P2 F26 1.580(4) . ? P2 F23 1.582(4) . ? P2 F22 1.586(4) . ? P2 F24 1.598(3) . ? P2 F21 1.612(3) . ? P3 F35 1.570(4) . ? P3 F31 1.582(4) . ? P3 F33 1.583(3) . ? P3 F34 1.586(3) . ? P3 F36 1.603(3) . ? P3 F32 1.624(3) . ? P4 F46 1.546(4) . ? P4 F41 1.553(4) . ? P4 F43 1.561(5) . ? P4 F44 1.574(5) . ? P4 F42 1.578(4) . ? P4 F45 1.586(4) . ? N1 C1 1.126(8) . ? C1 C2 1.465(9) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? N2 C3 1.138(7) . ? C3 C4 1.454(8) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? N3A C5A 1.206(16) . ? C5A C6A 1.420(19) . ? C6A H6A 0.9600 . ? C6A H6B 0.9600 . ? C6A H6C 0.9600 . ? N3B C5B 0.98(2) . ? C5B C6B 1.37(2) . ? C6B H6D 0.9600 . ? C6B H6E 0.9600 . ? C6B H6F 0.9600 . ? N4 C7 1.125(8) . ? C7 C8 1.468(8) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N5 C9 1.141(6) . ? C9 C10 1.461(7) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? O1W H1A 0.8501 . ? O1W H1B 0.8501 . ? 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 O31 C11 C16 114.9(4) . . ? O31 C11 C12 123.7(4) . . ? C16 C11 C12 121.3(4) . . ? C13 C12 C11 118.2(4) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? O41 C13 C12 115.0(4) . . ? O41 C13 C14 122.9(4) . . ? C12 C13 C14 122.2(4) . . ? C13 C14 C15 117.3(4) . . ? C13 C14 H14 121.4 . . ? C15 C14 H14 121.4 . . ? C16 C15 O51 116.2(4) . . ? C16 C15 C14 122.2(4) . . ? O51 C15 C14 121.6(4) . . ? C15 C16 C11 118.8(4) . . ? C15 C16 H16 120.6 . . ? C11 C16 H16 120.6 . . ? O35 C21 C26 116.3(4) . . ? O35 C21 C22 122.8(4) . . ? C26 C21 C22 121.0(4) . . ? C23 C22 C21 117.5(4) . . ? C23 C22 I1 132.9(11) . . ? C21 C22 I1 109.4(11) . . ? C23 C22 H22 121.2 . . ? C21 C22 H22 121.2 . . ? I1 C22 H22 12.3 . . ? O45 C23 C24 115.4(4) . . ? O45 C23 C22 123.6(4) . . ? C24 C23 C22 121.0(4) . . ? C25 C24 C23 120.8(4) . . ? C25 C24 I2 123.8(5) . . ? C23 C24 I2 115.0(5) . . ? C25 C24 H24A 119.6 . . ? C23 C24 H24A 119.6 . . ? I2 C24 H24A 8.2 . . ? O55 C25 C24 124.9(4) . . ? O55 C25 C26 115.7(4) . . ? C24 C25 C26 119.4(4) . . ? C25 C26 C21 120.3(4) . . ? C25 C26 I3 111.4(5) . . ? C21 C26 I3 128.2(6) . . ? C25 C26 H26A 119.9 . . ? C21 C26 H26A 119.9 . . ? I3 C26 H26A 9.3 . . ? C11 O31 C31 118.3(3) . . ? O31 C31 C32 107.2(4) . . ? O31 C31 H31A 110.3 . . ? C32 C31 H31A 110.3 . . ? O31 C31 H31B 110.3 . . ? C32 C31 H31B 110.3 . . ? H31A C31 H31B 108.5 . . ? O32 C32 C31 109.7(4) . . ? O32 C32 H32A 109.7 . . ? C31 C32 H32A 109.7 . . ? O32 C32 H32B 109.7 . . ? C31 C32 H32B 109.7 . . ? H32A C32 H32B 108.2 . . ? C32 O32 C33 111.0(4) . . ? O32 C33 C34 110.0(4) . . ? O32 C33 H33A 109.7 . . ? C34 C33 H33A 109.7 . . ? O32 C33 H33B 109.7 . . ? C34 C33 H33B 109.7 . . ? H33A C33 H33B 108.2 . . ? O33 C34 C33 109.3(4) . . ? O33 C34 H34A 109.8 . . ? C33 C34 H34A 109.8 . . ? O33 C34 H34B 109.8 . . ? C33 C34 H34B 109.8 . . ? H34A C34 H34B 108.3 . . ? C34 O33 C35 113.4(4) . . ? O33 C35 C36 115.5(4) . . ? O33 C35 H35A 108.4 . . ? C36 C35 H35A 108.4 . . ? O33 C35 H35B 108.4 . . ? C36 C35 H35B 108.4 . . ? H35A C35 H35B 107.5 . . ? O34 C36 C35 109.5(4) . . ? O34 C36 H36A 109.8 . . ? C35 C36 H36A 109.8 . . ? O34 C36 H36B 109.8 . . ? C35 C36 H36B 109.8 . . ? H36A C36 H36B 108.2 . . ? C36 O34 C37 111.3(4) . . ? O34 C37 C38 110.0(5) . . ? O34 C37 H37A 109.7 . . ? C38 C37 H37A 109.7 . . ? O34 C37 H37B 109.7 . . ? C38 C37 H37B 109.7 . . ? H37A C37 H37B 108.2 . . ? O35 C38 C37 109.4(6) . . ? O35 C38 H38A 109.8 . . ? C37 C38 H38A 109.8 . . ? O35 C38 H38B 109.8 . . ? C37 C38 H38B 109.8 . . ? H38A C38 H38B 108.2 . . ? C21 O35 C38 120.5(4) . . ? C13 O41 C41 118.4(3) . . ? O41 C41 C42 114.1(4) . . ? O41 C41 H41A 108.7 . . ? C42 C41 H41A 108.7 . . ? O41 C41 H41B 108.7 . . ? C42 C41 H41B 108.7 . . ? H41A C41 H41B 107.6 . . ? O42 C42 C41 109.5(4) . . ? O42 C42 H42A 109.8 . . ? C41 C42 H42A 109.8 . . ? O42 C42 H42B 109.8 . . ? C41 C42 H42B 109.8 . . ? H42A C42 H42B 108.2 . . ? C42 O42 C43 111.0(3) . . ? O42 C43 C44 107.8(4) . . ? O42 C43 H43A 110.1 . . ? C44 C43 H43A 110.1 . . ? O42 C43 H43B 110.1 . . ? C44 C43 H43B 110.1 . . ? H43A C43 H43B 108.4 . . ? O43 C44 C43 113.4(4) . . ? O43 C44 H44A 108.9 . . ? C43 C44 H44A 108.9 . . ? O43 C44 H44B 108.9 . . ? C43 C44 H44B 108.9 . . ? H44A C44 H44B 107.7 . . ? C45 O43 C44 112.2(3) . . ? O43 C45 C46 110.8(4) . . ? O43 C45 H45A 109.5 . . ? C46 C45 H45A 109.5 . . ? O43 C45 H45B 109.5 . . ? C46 C45 H45B 109.5 . . ? H45A C45 H45B 108.1 . . ? O44 C46 C45 111.2(4) . . ? O44 C46 H46A 109.4 . . ? C45 C46 H46A 109.4 . . ? O44 C46 H46B 109.4 . . ? C45 C46 H46B 109.4 . . ? H46A C46 H46B 108.0 . . ? C46 O44 C47 112.6(3) . . ? O44 C47 C48 109.9(4) . . ? O44 C47 H47A 109.7 . . ? C48 C47 H47A 109.7 . . ? O44 C47 H47B 109.7 . . ? C48 C47 H47B 109.7 . . ? H47A C47 H47B 108.2 . . ? O45 C48 C47 107.4(4) . . ? O45 C48 H48A 110.2 . . ? C47 C48 H48A 110.2 . . ? O45 C48 H48B 110.2 . . ? C47 C48 H48B 110.2 . . ? H48A C48 H48B 108.5 . . ? C23 O45 C48 119.1(4) . . ? C15 O51 C51 117.3(3) . . ? O51 C51 C52 109.6(4) . . ? O51 C51 H51A 109.8 . . ? C52 C51 H51A 109.8 . . ? O51 C51 H51B 109.8 . . ? C52 C51 H51B 109.8 . . ? H51A C51 H51B 108.2 . . ? O52 C52 C51 111.1(4) . . ? O52 C52 H52A 109.4 . . ? C51 C52 H52A 109.4 . . ? O52 C52 H52B 109.4 . . ? C51 C52 H52B 109.4 . . ? H52A C52 H52B 108.0 . . ? C52 O52 C53 110.1(4) . . ? O52 C53 C54 108.7(5) . . ? O52 C53 H53A 109.9 . . ? C54 C53 H53A 109.9 . . ? O52 C53 H53B 109.9 . . ? C54 C53 H53B 109.9 . . ? H53A C53 H53B 108.3 . . ? O53 C54 C53 108.6(5) . . ? O53 C54 H54A 110.0 . . ? C53 C54 H54A 110.0 . . ? O53 C54 H54B 110.0 . . ? C53 C54 H54B 110.0 . . ? H54A C54 H54B 108.4 . . ? C55 O53 C54 110.3(5) . . ? O53 C55 C56 109.0(5) . . ? O53 C55 H55A 109.9 . . ? C56 C55 H55A 109.9 . . ? O53 C55 H55B 109.9 . . ? C56 C55 H55B 109.9 . . ? H55A C55 H55B 108.3 . . ? O54 C56 C55 108.9(4) . . ? O54 C56 H56A 109.9 . . ? C55 C56 H56A 109.9 . . ? O54 C56 H56B 109.9 . . ? C55 C56 H56B 109.9 . . ? H56A C56 H56B 108.3 . . ? C57 O54 C56 112.3(4) . . ? O54 C57 C58 107.7(4) . . ? O54 C57 H57A 110.2 . . ? C58 C57 H57A 110.2 . . ? O54 C57 H57B 110.2 . . ? C58 C57 H57B 110.2 . . ? H57A C57 H57B 108.5 . . ? O55 C58 C57 107.7(4) . . ? O55 C58 H58A 110.2 . . ? C57 C58 H58A 110.2 . . ? O55 C58 H58B 110.2 . . ? C57 C58 H58B 110.2 . . ? H58A C58 H58B 108.5 . . ? C25 O55 C58 119.4(4) . . ? C62 C61 C66 119.5(4) . . ? C62 C61 C67 120.5(4) . . ? C66 C61 C67 119.8(4) . . ? C63 C62 C61 120.7(4) . . ? C63 C62 H62 119.6 . . ? C61 C62 H62 119.6 . . ? C62 C63 C64 119.9(4) . . ? C62 C63 H63 120.0 . . ? C64 C63 H63 120.0 . . ? C63 C64 C65 119.1(4) . . ? C63 C64 C68 120.5(4) . . ? C65 C64 C68 120.2(4) . . ? C66 C65 C64 120.8(4) . . ? C66 C65 H65 119.6 . . ? C64 C65 H65 119.6 . . ? C65 C66 C61 119.8(4) . . ? C65 C66 H66 120.1 . . ? C61 C66 H66 120.1 . . ? N81 C67 C61 108.3(3) . . ? N81 C67 H67A 110.0 . . ? C61 C67 H67A 110.0 . . ? N81 C67 H67B 110.0 . . ? C61 C67 H67B 110.0 . . ? H67A C67 H67B 108.4 . . ? N91 C68 C64 108.6(3) . . ? N91 C68 H68A 110.0 . . ? C64 C68 H68A 110.0 . . ? N91 C68 H68B 110.0 . . ? C64 C68 H68B 110.0 . . ? H68A C68 H68B 108.3 . . ? C72 C71 C76 118.8(5) . . ? C72 C71 C77 120.8(4) . . ? C76 C71 C77 120.2(5) . . ? C73 C72 C71 120.6(5) . . ? C73 C72 H72 119.7 . . ? C71 C72 H72 119.7 . . ? C72 C73 C74 120.1(5) . . ? C72 C73 H73 120.0 . . ? C74 C73 H73 120.0 . . ? C75 C74 C73 119.3(5) . . ? C75 C74 C78 120.3(5) . . ? C73 C74 C78 120.2(5) . . ? C76 C75 C74 120.8(5) . . ? C76 C75 H75 119.6 . . ? C74 C75 H75 119.6 . . ? C75 C76 C71 120.3(5) . . ? C75 C76 H76 119.9 . . ? C71 C76 H76 119.9 . . ? N82 C77 C71 109.1(4) . . ? N82 C77 H77A 109.9 . . ? C71 C77 H77A 109.9 . . ? N82 C77 H77B 109.9 . . ? C71 C77 H77B 109.9 . . ? H77A C77 H77B 108.3 . . ? N92 C78 C74 108.0(4) . . ? N92 C78 H78A 110.1 . . ? C74 C78 H78A 110.1 . . ? N92 C78 H78B 110.1 . . ? C74 C78 H78B 110.1 . . ? H78A C78 H78B 108.4 . . ? C84 C80 C81 117.7(4) . . ? C84 C80 C85 120.9(4) . . ? C81 C80 C85 121.3(4) . . ? C82 C81 C80 119.6(4) . . ? C82 C81 H81 120.2 . . ? C80 C81 H81 120.2 . . ? N81 C82 C81 120.9(4) . . ? N81 C82 H82 119.5 . . ? C81 C82 H82 119.5 . . ? C83 N81 C82 120.4(4) . . ? C83 N81 C67 119.8(4) . . ? C82 N81 C67 119.4(4) . . ? N81 C83 C84 120.6(4) . . ? N81 C83 H83 119.7 . . ? C84 C83 H83 119.7 . . ? C83 C84 C80 120.7(4) . . ? C83 C84 H84 119.7 . . ? C80 C84 H84 119.7 . . ? C86 C85 C89 117.3(5) . . ? C86 C85 C80 122.0(4) . . ? C89 C85 C80 120.6(4) . . ? C85 C86 C87 121.0(4) . . ? C85 C86 H86 119.5 . . ? C87 C86 H86 119.5 . . ? N82 C87 C86 120.0(5) . . ? N82 C87 H87 120.0 . . ? C86 C87 H87 120.0 . . ? C88 N82 C87 120.5(4) . . ? C88 N82 C77 119.4(4) . . ? C87 N82 C77 120.0(4) . . ? N82 C88 C89 121.5(5) . . ? N82 C88 H88 119.3 . . ? C89 C88 H88 119.3 . . ? C88 C89 C85 119.7(5) . . ? C88 C89 H89 120.2 . . ? C85 C89 H89 120.2 . . ? C91 C90 C94 117.8(4) . . ? C91 C90 C95 121.5(4) . . ? C94 C90 C95 120.6(4) . . ? C92 C91 C90 120.1(4) . . ? C92 C91 H91 119.9 . . ? C90 C91 H91 119.9 . . ? N91 C92 C91 120.5(4) . . ? N91 C92 H92 119.7 . . ? C91 C92 H92 119.7 . . ? C92 N91 C93 120.8(4) . . ? C92 N91 C68 119.4(4) . . ? C93 N91 C68 119.6(4) . . ? N91 C93 C94 120.8(4) . . ? N91 C93 H93 119.6 . . ? C94 C93 H93 119.6 . . ? C93 C94 C90 119.8(4) . . ? C93 C94 H94 120.1 . . ? C90 C94 H94 120.1 . . ? C99 C95 C96 117.7(4) . . ? C99 C95 C90 120.2(4) . . ? C96 C95 C90 121.9(4) . . ? C97 C96 C95 120.1(4) . . ? C97 C96 H96 120.0 . . ? C95 C96 H96 120.0 . . ? N92 C97 C96 120.2(4) . . ? N92 C97 H97 119.9 . . ? C96 C97 H97 119.9 . . ? C98 N92 C97 121.1(4) . . ? C98 N92 C78 119.7(4) . . ? C97 N92 C78 118.8(4) . . ? N92 C98 C99 120.7(4) . . ? N92 C98 H98 119.6 . . ? C99 C98 H98 119.6 . . ? C98 C99 C95 120.1(4) . . ? C98 C99 H99 119.9 . . ? C95 C99 H99 119.9 . . ? F13 P1 F14 91.69(18) . . ? F13 P1 F15 90.7(2) . . ? F14 P1 F15 90.6(3) . . ? F13 P1 F11 89.9(2) . . ? F14 P1 F11 178.4(2) . . ? F15 P1 F11 89.2(3) . . ? F13 P1 F16 178.9(2) . . ? F14 P1 F16 89.3(2) . . ? F15 P1 F16 89.8(2) . . ? F11 P1 F16 89.1(2) . . ? F13 P1 F12 90.6(2) . . ? F14 P1 F12 90.2(2) . . ? F15 P1 F12 178.5(2) . . ? F11 P1 F12 89.9(2) . . ? F16 P1 F12 88.9(2) . . ? F25 P2 F26 91.6(3) . . ? F25 P2 F23 89.5(3) . . ? F26 P2 F23 178.0(2) . . ? F25 P2 F22 178.1(3) . . ? F26 P2 F22 90.0(3) . . ? F23 P2 F22 88.9(3) . . ? F25 P2 F24 90.42(19) . . ? F26 P2 F24 90.5(2) . . ? F23 P2 F24 91.08(19) . . ? F22 P2 F24 90.47(19) . . ? F25 P2 F21 90.67(19) . . ? F26 P2 F21 89.35(19) . . ? F23 P2 F21 89.01(19) . . ? F22 P2 F21 88.43(19) . . ? F24 P2 F21 178.90(18) . . ? F35 P3 F31 92.3(3) . . ? F35 P3 F33 89.3(2) . . ? F31 P3 F33 91.9(2) . . ? F35 P3 F34 90.3(2) . . ? F31 P3 F34 177.0(2) . . ? F33 P3 F34 89.7(2) . . ? F35 P3 F36 91.5(2) . . ? F31 P3 F36 88.3(2) . . ? F33 P3 F36 179.2(2) . . ? F34 P3 F36 90.10(19) . . ? F35 P3 F32 178.6(2) . . ? F31 P3 F32 89.0(2) . . ? F33 P3 F32 90.4(2) . . ? F34 P3 F32 88.4(2) . . ? F36 P3 F32 88.82(17) . . ? F46 P4 F41 89.8(3) . . ? F46 P4 F43 179.74(17) . . ? F41 P4 F43 90.4(3) . . ? F46 P4 F44 89.9(3) . . ? F41 P4 F44 179.74(18) . . ? F43 P4 F44 89.8(3) . . ? F46 P4 F42 90.7(2) . . ? F41 P4 F42 92.9(2) . . ? F43 P4 F42 89.4(2) . . ? F44 P4 F42 87.2(2) . . ? F46 P4 F45 89.4(2) . . ? F41 P4 F45 87.8(2) . . ? F43 P4 F45 90.5(2) . . ? F44 P4 F45 92.1(2) . . ? F42 P4 F45 179.30(14) . . ? N1 C1 C2 177.5(7) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 179.3(7) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3A C5A C6A 173.2(14) . . ? N3B C5B C6B 174(2) . . ? C5B C6B H6D 109.5 . . ? C5B C6B H6E 109.5 . . ? H6D C6B H6E 109.5 . . ? C5B C6B H6F 109.5 . . ? H6D C6B H6F 109.5 . . ? H6E C6B H6F 109.5 . . ? N4 C7 C8 179.4(8) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 C10 179.6(6) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? H1A O1W H1B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.135 _refine_diff_density_min -1.763 _refine_diff_density_rms 0.104 _publ_section_exptl_refinement ; Three H atoms from one of the benzene rings are partly substituted by iodine atoms. All these H and I atoms were refined anisotropically and the occupancies of three iodine atoms converged to 0.0109(16), 0.0383(18) and 0.0249(16) for I1, I2 and I3, respectively. Thus they were fixed at 0.01, 0.04 and 0.025, respectively, while the occupancies of H22, H24 and H26 were fixed at 0.99, 0.96 and 0.975, respectively. Furthermore, the distance of C---I was fixed at around 2.1\%A. One of the acetonitrile molecules is disordered in the structure. The non-hydrongen atoms in two positions were refined isotropically and the occupancies converged to 0.546(9) (N3A, C5A and C6A) and 0.454(9) (N3B, C5B and C6B), respectively. All of these atoms, including their riding H atoms, were fixed at 0.5 in the final cycles of refinement. The H atoms of the water were placed in a calculated position (Nardelli, 1999), and included in the final cycles of refinement with fixed coordinates and an isotropic displacement parameter of 0.08 \%A^2^. Other H atoms were placed in calculated positions, with C---H = 0.93 - 0.97 \%A, and included in the final cycles of refinement in a riding model, with U~iso~(H) = 1.2U~eq~ or 1.5U~eq~ of the carrier atoms. ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. Nardelli, M. (1999). J. Appl. Cryst. 32, 563-571. Sheldrick, G. M. (1997). SHELXL-97. University of G\"ottingen, Germany. ; #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 701930' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(m-phenylene)-32-crown-10-Based Cryptand/Paraquat [3]Catenane ; _chemical_name_common ;Bis(m-phenylene)-32-crown-10-Based Cryptand/Paraquat (3)Catenane ; _chemical_melting_point 537(2) _chemical_formula_moiety 'C36 H54 O15, 0.5(C48 H40 N4), 2(F6 P), 5(C2 H3 N), 5(H2 O)' _chemical_formula_sum 'C70 H99 F12 N7 O20 P2' _chemical_formula_weight 1648.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.196(4) _cell_length_b 14.757(3) _cell_length_c 28.726(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.64(3) _cell_angle_gamma 90.00 _cell_volume 8552(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 77143 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.4 _exptl_crystal_description platelet _exptl_crystal_colour orange _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3464 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count image _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 62628 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.24 _reflns_number_total 15437 _reflns_number_gt 11651 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku, 1998)' _computing_cell_refinement 'RAPID-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2002)' _computing_structure_solution 'SIR-92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0832P)^2^+3.5173P] 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 15437 _refine_ls_number_parameters 969 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1413 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C11 C 0.09473(11) 0.33759(18) 0.43981(9) 0.0306(6) Uani 1 1 d . . . C12 C 0.09545(11) 0.36303(17) 0.48635(9) 0.0287(5) Uani 1 1 d . . . H12 H 0.1015 0.3201 0.5099 0.034 Uiso 1 1 calc R . . C13 C 0.08693(11) 0.45410(17) 0.49708(8) 0.0275(5) Uani 1 1 d . . . C14 C 0.07827(11) 0.51873(18) 0.46252(8) 0.0293(5) Uani 1 1 d . . . H14 H 0.0721 0.5794 0.4700 0.035 Uiso 1 1 calc R . . C15 C 0.07907(11) 0.49073(18) 0.41618(9) 0.0306(6) Uani 1 1 d . . . C16 C 0.08728(11) 0.40116(18) 0.40453(9) 0.0313(6) Uani 1 1 d . . . H16 H 0.0878 0.3836 0.3735 0.038 Uiso 1 1 calc R . . C21 C 0.42114(10) 0.37617(15) 0.40281(8) 0.0206(5) Uani 1 1 d . . . C22 C 0.41400(10) 0.39964(16) 0.44899(8) 0.0217(5) Uani 1 1 d . . . H22 H 0.4123 0.3551 0.4718 0.026 Uiso 1 1 calc R . . C23 C 0.40941(10) 0.49065(16) 0.46082(7) 0.0208(5) Uani 1 1 d . . . C24 C 0.41208(11) 0.55730(16) 0.42725(8) 0.0238(5) Uani 1 1 d . . . H24 H 0.4086 0.6181 0.4353 0.029 Uiso 1 1 calc R . . C25 C 0.42000(11) 0.53218(16) 0.38114(8) 0.0236(5) Uani 1 1 d . . . C26 C 0.42344(10) 0.44198(15) 0.36807(7) 0.0217(5) Uani 1 1 d . . . H26 H 0.4272 0.4258 0.3370 0.026 Uiso 1 1 calc R . . O11 O 0.10126(9) 0.25003(12) 0.42502(6) 0.0362(4) Uani 1 1 d . . . C31 C 0.10701(12) 0.18119(18) 0.45968(9) 0.0334(6) Uani 1 1 d . . . H31A H 0.0711 0.1864 0.4808 0.040 Uiso 1 1 calc R . . H31B H 0.1486 0.1877 0.4776 0.040 Uiso 1 1 calc R . . C32 C 0.10427(12) 0.09078(18) 0.43604(10) 0.0361(6) Uani 1 1 d . . . H32A H 0.1055 0.0430 0.4592 0.043 Uiso 1 1 calc R . . H32B H 0.0631 0.0853 0.4174 0.043 Uiso 1 1 calc R . . O12 O 0.15930(8) 0.08145(11) 0.40677(6) 0.0358(4) Uani 1 1 d . . . C33 C 0.16394(14) -0.00879(18) 0.38992(11) 0.0410(7) Uani 1 1 d . . . H33A H 0.1203 -0.0303 0.3797 0.049 Uiso 1 1 calc R . . H33B H 0.1809 -0.0481 0.4148 0.049 Uiso 1 1 calc R . . C34 C 0.20910(13) -0.01211(18) 0.35008(9) 0.0358(6) Uani 1 1 d . . . H34A H 0.2089 -0.0727 0.3370 0.043 Uiso 1 1 calc R . . H34B H 0.1934 0.0296 0.3259 0.043 Uiso 1 1 calc R . . O13 O 0.27463(8) 0.01167(11) 0.36555(5) 0.0283(4) Uani 1 1 d . . . C35 C 0.31989(13) -0.00673(17) 0.33067(9) 0.0344(6) Uani 1 1 d . . . H35A H 0.3050 0.0225 0.3018 0.041 Uiso 1 1 calc R . . H35B H 0.3216 -0.0715 0.3252 0.041 Uiso 1 1 calc R . . C36 C 0.38728(13) 0.02681(16) 0.34510(10) 0.0350(6) Uani 1 1 d . . . H36A H 0.4008 0.0020 0.3753 0.042 Uiso 1 1 calc R . . H36B H 0.4189 0.0072 0.3228 0.042 Uiso 1 1 calc R . . O14 O 0.38633(8) 0.12292(10) 0.34738(5) 0.0270(4) Uani 1 1 d . . . C37 C 0.45087(11) 0.16082(16) 0.34540(8) 0.0271(5) Uani 1 1 d . . . H37A H 0.4707 0.1431 0.3167 0.033 Uiso 1 1 calc R . . H37B H 0.4789 0.1390 0.3714 0.033 Uiso 1 1 calc R . . C38 C 0.44487(12) 0.26123(16) 0.34762(8) 0.0256(5) Uani 1 1 d . . . H38A H 0.4867 0.2893 0.3405 0.031 Uiso 1 1 calc R . . H38B H 0.4111 0.2820 0.3250 0.031 Uiso 1 1 calc R . . O15 O 0.42714(8) 0.28586(10) 0.39386(5) 0.0239(3) Uani 1 1 d . . . O31 O 0.08692(8) 0.47291(11) 0.54372(6) 0.0298(4) Uani 1 1 d . . . C41 C 0.08214(12) 0.56584(17) 0.55690(8) 0.0295(5) Uani 1 1 d . . . H41A H 0.0412 0.5918 0.5439 0.035 Uiso 1 1 calc R . . H41B H 0.1190 0.5999 0.5452 0.035 Uiso 1 1 calc R . . C42 C 0.08347(12) 0.57031(18) 0.60884(9) 0.0322(6) Uani 1 1 d . . . H42A H 0.0762 0.6322 0.6188 0.039 Uiso 1 1 calc R . . H42B H 0.0486 0.5326 0.6205 0.039 Uiso 1 1 calc R . . O32 O 0.14641(8) 0.53930(12) 0.62669(6) 0.0322(4) Uani 1 1 d . . . C43 C 0.15502(12) 0.5496(2) 0.67583(8) 0.0369(6) Uani 1 1 d . . . H43A H 0.1203 0.5175 0.6913 0.044 Uiso 1 1 calc R . . H43B H 0.1529 0.6131 0.6842 0.044 Uiso 1 1 calc R . . C44 C 0.22136(12) 0.5113(2) 0.69032(8) 0.0348(6) Uani 1 1 d . . . H44A H 0.2279 0.5141 0.7239 0.042 Uiso 1 1 calc R . . H44B H 0.2238 0.4483 0.6809 0.042 Uiso 1 1 calc R . . O33 O 0.27108(8) 0.56194(12) 0.66909(5) 0.0290(4) Uani 1 1 d . . . C45 C 0.33491(11) 0.52148(19) 0.67555(8) 0.0317(6) Uani 1 1 d . . . H45A H 0.3333 0.4591 0.6649 0.038 Uiso 1 1 calc R . . H45B H 0.3486 0.5218 0.7084 0.038 Uiso 1 1 calc R . . C46 C 0.38356(12) 0.57383(19) 0.64843(8) 0.0321(6) Uani 1 1 d . . . H46A H 0.3830 0.6370 0.6577 0.039 Uiso 1 1 calc R . . H46B H 0.4279 0.5504 0.6550 0.039 Uiso 1 1 calc R . . O34 O 0.36674(7) 0.56624(12) 0.59979(5) 0.0278(4) Uani 1 1 d . . . C47 C 0.41857(12) 0.60294(18) 0.57343(8) 0.0298(5) Uani 1 1 d . . . H47A H 0.4590 0.5689 0.5802 0.036 Uiso 1 1 calc R . . H47B H 0.4266 0.6652 0.5829 0.036 Uiso 1 1 calc R . . C48 C 0.40219(12) 0.60018(16) 0.52225(8) 0.0273(5) Uani 1 1 d . . . H48A H 0.3589 0.6269 0.5155 0.033 Uiso 1 1 calc R . . H48B H 0.4347 0.6345 0.5058 0.033 Uiso 1 1 calc R . . O35 O 0.40226(8) 0.50726(11) 0.50718(5) 0.0250(4) Uani 1 1 d . . . O51 O 0.07073(8) 0.54837(12) 0.37914(6) 0.0357(4) Uani 1 1 d . . . C51 C 0.05779(13) 0.64147(19) 0.38884(10) 0.0401(6) Uani 1 1 d . . . H51A H 0.0935 0.6667 0.4085 0.048 Uiso 1 1 calc R . . H51B H 0.0168 0.6472 0.4050 0.048 Uiso 1 1 calc R . . C52 C 0.05228(15) 0.6911(2) 0.34303(10) 0.0493(8) Uani 1 1 d . . . H52A H 0.0183 0.6630 0.3228 0.059 Uiso 1 1 calc R . . H52B H 0.0396 0.7535 0.3482 0.059 Uiso 1 1 calc R . . O52 O 0.11367(9) 0.68835(14) 0.32158(7) 0.0459(5) Uani 1 1 d . . . C53 C 0.11081(15) 0.7349(2) 0.27745(10) 0.0530(8) Uani 1 1 d . . . H53A H 0.1025 0.7989 0.2822 0.064 Uiso 1 1 calc R . . H53B H 0.0750 0.7106 0.2575 0.064 Uiso 1 1 calc R . . C54 C 0.17623(15) 0.7223(2) 0.25462(10) 0.0461(7) Uani 1 1 d . . . H54A H 0.1878 0.6585 0.2541 0.055 Uiso 1 1 calc R . . H54B H 0.1728 0.7440 0.2227 0.055 Uiso 1 1 calc R . . O53 O 0.22490(10) 0.77101(13) 0.28010(6) 0.0405(4) Uani 1 1 d . . . C55 C 0.28548(14) 0.77852(19) 0.25576(9) 0.0399(6) Uani 1 1 d . . . H55A H 0.3171 0.8132 0.2750 0.048 Uiso 1 1 calc R . . H55B H 0.2763 0.8126 0.2273 0.048 Uiso 1 1 calc R . . C56 C 0.31687(14) 0.69134(18) 0.24344(9) 0.0370(6) Uani 1 1 d . . . H56A H 0.2910 0.6622 0.2184 0.044 Uiso 1 1 calc R . . H56B H 0.3611 0.7022 0.2329 0.044 Uiso 1 1 calc R . . O54 O 0.31999(9) 0.63574(12) 0.28255(6) 0.0362(4) Uani 1 1 d . . . C57 C 0.36630(13) 0.56087(17) 0.27955(9) 0.0355(6) Uani 1 1 d . . . H57A H 0.3721 0.5463 0.2471 0.043 Uiso 1 1 calc R . . H57B H 0.3484 0.5079 0.2945 0.043 Uiso 1 1 calc R . . C58 C 0.43100(14) 0.58390(18) 0.30219(8) 0.0346(6) Uani 1 1 d . . . H58A H 0.4614 0.5339 0.2985 0.041 Uiso 1 1 calc R . . H58B H 0.4490 0.6366 0.2870 0.041 Uiso 1 1 calc R . . O55 O 0.42582(9) 0.60270(11) 0.35094(5) 0.0318(4) Uani 1 1 d . . . C60 C 0.69099(11) 0.91174(15) 0.52318(8) 0.0240(5) Uani 1 1 d . . . H60A H 0.7191 0.9362 0.4998 0.029 Uiso 1 1 calc R . . H60B H 0.6935 0.9516 0.5501 0.029 Uiso 1 1 calc R . . C61 C 0.48989(11) 0.87505(14) 0.46845(7) 0.0207(5) Uani 1 1 d . . . C62 C 0.53890(11) 0.90638(15) 0.43967(8) 0.0253(5) Uani 1 1 d . . . H62 H 0.5283 0.9175 0.4083 0.030 Uiso 1 1 calc R . . C63 C 0.60361(11) 0.92126(15) 0.45721(8) 0.0246(5) Uani 1 1 d . . . H63 H 0.6356 0.9417 0.4375 0.030 Uiso 1 1 calc R . . C64 C 0.62045(11) 0.90574(15) 0.50393(7) 0.0215(5) Uani 1 1 d . . . C65 C 0.57097(11) 0.87820(16) 0.53288(8) 0.0244(5) Uani 1 1 d . . . H65 H 0.5811 0.8697 0.5645 0.029 Uiso 1 1 calc R . . C66 C 0.50692(11) 0.86318(15) 0.51553(8) 0.0241(5) Uani 1 1 d . . . H66 H 0.4747 0.8448 0.5356 0.029 Uiso 1 1 calc R . . C71 C 0.42328(11) 0.84834(14) 0.44938(7) 0.0201(5) Uani 1 1 d . . . C72 C 0.41601(11) 0.81053(15) 0.40474(8) 0.0230(5) Uani 1 1 d . . . H72 H 0.4525 0.8075 0.3862 0.028 Uiso 1 1 calc R . . C73 C 0.35540(11) 0.77750(15) 0.38762(8) 0.0234(5) Uani 1 1 d . . . H73 H 0.3519 0.7522 0.3580 0.028 Uiso 1 1 calc R . . C74 C 0.30000(11) 0.78171(15) 0.41420(8) 0.0222(5) Uani 1 1 d . . . C75 C 0.30592(11) 0.82222(15) 0.45830(8) 0.0249(5) Uani 1 1 d . . . H75 H 0.2689 0.8274 0.4762 0.030 Uiso 1 1 calc R . . C76 C 0.36663(11) 0.85451(15) 0.47540(8) 0.0240(5) Uani 1 1 d . . . H76 H 0.3698 0.8809 0.5048 0.029 Uiso 1 1 calc R . . C80 C 0.23622(11) 0.73831(15) 0.39663(8) 0.0240(5) Uani 1 1 d . . . H80A H 0.1992 0.7657 0.4118 0.029 Uiso 1 1 calc R . . H80B H 0.2300 0.7482 0.3633 0.029 Uiso 1 1 calc R . . C81 C 0.24839(10) 0.45599(15) 0.42732(7) 0.0188(4) Uani 1 1 d . . . C82 C 0.24085(10) 0.52059(15) 0.46231(8) 0.0215(5) Uani 1 1 d . . . H82 H 0.2391 0.5025 0.4932 0.026 Uiso 1 1 calc R . . C83 C 0.23605(10) 0.61058(16) 0.45084(8) 0.0227(5) Uani 1 1 d . . . H83 H 0.2313 0.6531 0.4744 0.027 Uiso 1 1 calc R . . N84 N 0.23799(9) 0.63887(12) 0.40652(6) 0.0208(4) Uani 1 1 d . . . C85 C 0.24398(11) 0.57812(15) 0.37196(8) 0.0230(5) Uani 1 1 d . . . H85 H 0.2446 0.5979 0.3412 0.028 Uiso 1 1 calc R . . C86 C 0.24918(11) 0.48726(15) 0.38170(8) 0.0234(5) Uani 1 1 d . . . H86 H 0.2533 0.4461 0.3575 0.028 Uiso 1 1 calc R . . C91 C 0.74251(10) 0.64118(15) 0.56027(7) 0.0192(5) Uani 1 1 d . . . C92 C 0.73660(10) 0.66909(15) 0.51363(7) 0.0215(5) Uani 1 1 d . . . H92 H 0.7424 0.6274 0.4899 0.026 Uiso 1 1 calc R . . C93 C 0.72238(10) 0.75711(15) 0.50289(8) 0.0220(5) Uani 1 1 d . . . H93 H 0.7185 0.7749 0.4718 0.026 Uiso 1 1 calc R . . N94 N 0.71379(9) 0.81889(12) 0.53693(6) 0.0214(4) Uani 1 1 d . . . C95 C 0.72179(10) 0.79542(15) 0.58183(8) 0.0221(5) Uani 1 1 d . . . H95 H 0.7174 0.8390 0.6049 0.027 Uiso 1 1 calc R . . C96 C 0.73635(10) 0.70753(15) 0.59408(8) 0.0220(5) Uani 1 1 d . . . H96 H 0.7422 0.6922 0.6254 0.026 Uiso 1 1 calc R . . P1 P 0.48678(3) 0.35199(4) 0.22239(2) 0.02935(16) Uani 1 1 d . . . F11 F 0.47354(8) 0.43897(14) 0.19194(7) 0.0659(6) Uani 1 1 d . . . F12 F 0.52199(9) 0.41084(15) 0.26180(7) 0.0706(6) Uani 1 1 d . . . F13 F 0.41749(8) 0.36782(11) 0.24634(5) 0.0417(4) Uani 1 1 d . . . F14 F 0.49910(13) 0.26439(14) 0.25269(8) 0.0929(9) Uani 1 1 d . . . F15 F 0.45166(11) 0.29281(18) 0.18317(8) 0.0951(9) Uani 1 1 d . . . F16 F 0.55631(7) 0.33691(11) 0.19928(5) 0.0394(4) Uani 1 1 d . . . P2 P 0.08799(3) 0.82049(5) 0.49617(3) 0.03946(19) Uani 1 1 d . . . F21 F 0.03485(8) 0.89984(11) 0.49748(6) 0.0497(4) Uani 1 1 d . . . F22 F 0.14645(8) 0.89101(12) 0.50601(6) 0.0513(4) Uani 1 1 d . . . F23 F 0.08236(9) 0.80353(13) 0.55035(6) 0.0611(5) Uani 1 1 d . . . F24 F 0.14193(8) 0.74087(11) 0.49413(6) 0.0533(5) Uani 1 1 d . . . F25 F 0.03043(8) 0.74849(11) 0.48562(7) 0.0558(5) Uani 1 1 d . . . F26 F 0.09362(8) 0.83513(11) 0.44140(6) 0.0491(4) Uani 1 1 d . . . N1 N 0.73733(14) 0.65300(19) 0.71049(8) 0.0529(7) Uani 1 1 d . . . C1 C 0.71951(14) 0.7101(2) 0.73303(9) 0.0402(7) Uani 1 1 d . . . C2 C 0.69563(17) 0.7839(2) 0.76110(11) 0.0510(8) Uani 1 1 d . . . H2A H 0.7310 0.8261 0.7677 0.077 Uiso 1 1 calc R . . H2B H 0.6803 0.7602 0.7898 0.077 Uiso 1 1 calc R . . H2C H 0.6598 0.8142 0.7444 0.077 Uiso 1 1 calc R . . N2 N 0.80750(14) 0.90242(19) 0.43992(9) 0.0558(7) Uani 1 1 d . . . C3 C 0.85560(16) 0.9328(2) 0.42780(10) 0.0473(7) Uani 1 1 d . . . C4 C 0.91757(16) 0.9701(3) 0.41150(12) 0.0622(9) Uani 1 1 d . . . H4A H 0.9537 0.9519 0.4323 0.093 Uiso 1 1 calc R . . H4B H 0.9149 1.0350 0.4108 0.093 Uiso 1 1 calc R . . H4C H 0.9248 0.9478 0.3807 0.093 Uiso 1 1 calc R . . N3 N 0.31414(13) 0.22752(18) 0.11553(8) 0.0473(6) Uani 1 1 d . . . C5 C 0.36417(14) 0.19993(18) 0.10473(9) 0.0345(6) Uani 1 1 d . . . C6 C 0.42624(14) 0.16467(19) 0.09019(10) 0.0425(7) Uani 1 1 d . . . H6A H 0.4190 0.1071 0.0753 0.064 Uiso 1 1 calc R . . H6B H 0.4561 0.1573 0.1169 0.064 Uiso 1 1 calc R . . H6C H 0.4451 0.2061 0.0687 0.064 Uiso 1 1 calc R . . N4 N 0.6452(2) 0.1725(3) 0.39708(12) 0.0838(10) Uani 1 1 d . . . C7 C 0.6970(2) 0.2041(2) 0.39751(11) 0.0610(9) Uani 1 1 d . . . C8 C 0.76255(19) 0.2463(3) 0.39757(13) 0.0688(10) Uani 1 1 d . . . H8A H 0.7587 0.3060 0.3844 0.103 Uiso 1 1 calc R . . H8B H 0.7913 0.2103 0.3793 0.103 Uiso 1 1 calc R . . H8C H 0.7807 0.2504 0.4290 0.103 Uiso 1 1 calc R . . N5 N 0.19721(18) 0.5518(3) 0.16941(12) 0.0843(11) Uani 1 1 d . . . C9 C 0.24196(19) 0.5036(3) 0.16629(11) 0.0566(9) Uani 1 1 d . . . C10 C 0.29869(19) 0.4461(3) 0.16198(12) 0.0647(10) Uani 1 1 d . . . H10A H 0.2876 0.3973 0.1409 0.097 Uiso 1 1 calc R . . H10B H 0.3119 0.4219 0.1920 0.097 Uiso 1 1 calc R . . H10C H 0.3345 0.4807 0.1501 0.097 Uiso 1 1 calc R . . O1W O 0.24699(8) 0.48085(12) 0.56838(5) 0.0324(4) Uani 1 1 d . . . H1A H 0.2847 0.5131 0.5800 0.080 Uiso 1 1 d R . . H1B H 0.2163 0.5025 0.5882 0.080 Uiso 1 1 d R . . 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 C11 0.0189(11) 0.0349(15) 0.0383(14) -0.0106(11) 0.0036(10) -0.0013(10) C12 0.0199(11) 0.0303(14) 0.0360(14) -0.0009(11) 0.0006(10) 0.0002(10) C13 0.0159(11) 0.0332(14) 0.0333(13) -0.0059(11) 0.0014(9) -0.0012(10) C14 0.0187(11) 0.0314(14) 0.0375(14) -0.0029(11) -0.0015(10) 0.0008(10) C15 0.0184(11) 0.0397(15) 0.0333(13) 0.0007(11) -0.0018(9) -0.0044(11) C16 0.0228(12) 0.0399(16) 0.0313(13) -0.0052(11) 0.0024(10) -0.0037(11) C21 0.0178(10) 0.0180(11) 0.0260(12) 0.0001(9) 0.0010(8) 0.0005(9) C22 0.0167(10) 0.0246(12) 0.0237(11) 0.0055(9) 0.0021(8) -0.0005(9) C23 0.0173(10) 0.0274(13) 0.0178(11) -0.0004(9) 0.0019(8) 0.0004(9) C24 0.0278(12) 0.0188(12) 0.0249(12) -0.0001(9) 0.0023(9) 0.0000(10) C25 0.0244(11) 0.0211(12) 0.0254(12) 0.0041(9) 0.0010(9) 0.0005(10) C26 0.0240(11) 0.0218(12) 0.0193(11) 0.0002(9) 0.0029(8) 0.0013(9) O11 0.0393(10) 0.0322(10) 0.0376(10) -0.0060(8) 0.0061(8) 0.0006(8) C31 0.0269(12) 0.0344(15) 0.0393(15) -0.0061(11) 0.0075(10) -0.0018(11) C32 0.0280(13) 0.0340(15) 0.0473(16) -0.0082(12) 0.0118(11) -0.0093(11) O12 0.0354(10) 0.0247(9) 0.0486(11) -0.0104(8) 0.0150(8) -0.0066(8) C33 0.0418(15) 0.0271(14) 0.0550(17) -0.0121(12) 0.0122(13) -0.0106(12) C34 0.0385(14) 0.0300(14) 0.0390(15) -0.0110(11) 0.0021(11) -0.0035(12) O13 0.0338(9) 0.0245(9) 0.0267(9) -0.0050(7) 0.0046(7) -0.0023(7) C35 0.0491(16) 0.0228(13) 0.0321(14) -0.0089(10) 0.0094(11) -0.0004(12) C36 0.0400(15) 0.0195(13) 0.0465(16) -0.0033(11) 0.0130(12) 0.0030(11) O14 0.0325(9) 0.0175(8) 0.0314(9) 0.0006(7) 0.0065(7) 0.0017(7) C37 0.0302(12) 0.0266(13) 0.0252(12) 0.0009(10) 0.0086(9) 0.0012(10) C38 0.0311(12) 0.0247(13) 0.0212(11) 0.0004(9) 0.0054(9) 0.0007(10) O15 0.0316(9) 0.0193(8) 0.0212(8) 0.0013(6) 0.0058(6) 0.0005(7) O31 0.0283(9) 0.0281(9) 0.0328(9) -0.0045(7) -0.0018(7) 0.0013(7) C41 0.0233(12) 0.0277(13) 0.0373(14) -0.0019(11) -0.0015(10) 0.0003(10) C42 0.0243(12) 0.0349(15) 0.0374(14) -0.0055(11) 0.0016(10) 0.0021(11) O32 0.0237(8) 0.0454(11) 0.0273(9) -0.0079(8) 0.0000(7) 0.0020(8) C43 0.0284(13) 0.0574(18) 0.0253(13) -0.0097(12) 0.0055(10) -0.0047(12) C44 0.0319(13) 0.0510(17) 0.0216(12) 0.0019(11) 0.0029(10) -0.0090(12) O33 0.0237(8) 0.0401(10) 0.0231(8) -0.0048(7) 0.0016(6) -0.0032(7) C45 0.0282(13) 0.0449(16) 0.0219(12) -0.0008(11) -0.0004(9) 0.0032(12) C46 0.0264(12) 0.0475(16) 0.0221(12) -0.0045(11) -0.0019(9) -0.0027(12) O34 0.0235(8) 0.0408(10) 0.0192(8) -0.0046(7) 0.0015(6) -0.0053(7) C47 0.0269(12) 0.0368(15) 0.0258(12) -0.0039(10) 0.0031(9) -0.0074(11) C48 0.0312(13) 0.0254(13) 0.0256(12) -0.0032(10) 0.0034(9) -0.0025(10) O35 0.0320(9) 0.0240(9) 0.0193(8) -0.0012(6) 0.0048(6) -0.0010(7) O51 0.0349(9) 0.0372(11) 0.0348(10) 0.0029(8) -0.0021(7) -0.0016(8) C51 0.0328(14) 0.0441(17) 0.0428(16) 0.0017(13) -0.0033(11) 0.0027(13) C52 0.0486(17) 0.0489(19) 0.0491(18) 0.0072(14) -0.0108(14) 0.0103(15) O52 0.0409(11) 0.0553(13) 0.0411(11) 0.0170(9) -0.0025(8) 0.0032(9) C53 0.0522(18) 0.064(2) 0.0419(17) 0.0189(15) -0.0087(14) 0.0029(16) C54 0.0607(19) 0.0458(18) 0.0306(15) 0.0074(13) -0.0100(13) 0.0007(15) O53 0.0562(12) 0.0341(11) 0.0310(10) -0.0001(8) -0.0016(8) -0.0024(9) C55 0.0474(16) 0.0391(16) 0.0331(14) 0.0079(12) 0.0021(12) -0.0022(13) C56 0.0468(16) 0.0369(16) 0.0273(13) 0.0009(11) 0.0006(11) -0.0030(13) O54 0.0452(10) 0.0377(11) 0.0261(9) 0.0009(8) 0.0050(7) 0.0041(9) C57 0.0502(16) 0.0245(13) 0.0323(14) -0.0003(11) 0.0072(11) 0.0054(12) C58 0.0536(16) 0.0261(14) 0.0247(13) 0.0042(10) 0.0100(11) 0.0074(12) O55 0.0532(11) 0.0211(9) 0.0215(8) 0.0039(7) 0.0054(7) 0.0023(8) C60 0.0294(12) 0.0159(11) 0.0267(12) 0.0014(9) 0.0007(9) 0.0003(10) C61 0.0274(12) 0.0135(11) 0.0213(11) -0.0006(8) 0.0016(9) 0.0027(9) C62 0.0326(13) 0.0222(12) 0.0209(11) 0.0027(9) 0.0001(9) 0.0000(10) C63 0.0278(12) 0.0220(12) 0.0244(12) 0.0025(9) 0.0053(9) -0.0021(10) C64 0.0279(12) 0.0140(11) 0.0227(11) -0.0010(9) 0.0011(9) 0.0010(9) C65 0.0331(13) 0.0228(12) 0.0172(11) 0.0012(9) 0.0010(9) -0.0008(10) C66 0.0278(12) 0.0231(12) 0.0217(11) 0.0018(9) 0.0051(9) -0.0016(10) C71 0.0258(11) 0.0137(11) 0.0207(11) 0.0028(8) 0.0000(9) 0.0010(9) C72 0.0295(12) 0.0179(12) 0.0222(11) 0.0019(9) 0.0060(9) 0.0018(10) C73 0.0333(13) 0.0168(11) 0.0200(11) -0.0014(9) 0.0001(9) 0.0022(10) C74 0.0287(12) 0.0136(11) 0.0239(11) 0.0022(9) -0.0021(9) 0.0016(9) C75 0.0287(12) 0.0193(12) 0.0269(12) 0.0005(9) 0.0042(9) 0.0043(10) C76 0.0324(12) 0.0193(12) 0.0203(11) -0.0024(9) 0.0007(9) 0.0003(10) C80 0.0276(12) 0.0170(12) 0.0269(12) 0.0006(9) -0.0020(9) 0.0023(10) C81 0.0148(10) 0.0199(12) 0.0217(11) -0.0014(9) -0.0009(8) -0.0022(9) C82 0.0197(11) 0.0228(12) 0.0219(11) 0.0011(9) -0.0004(8) -0.0001(9) C83 0.0230(11) 0.0225(12) 0.0224(11) -0.0041(9) -0.0001(9) 0.0009(10) N84 0.0212(9) 0.0182(10) 0.0227(10) 0.0003(7) -0.0010(7) 0.0003(8) C85 0.0246(11) 0.0236(12) 0.0207(11) 0.0002(9) -0.0008(9) -0.0003(10) C86 0.0253(11) 0.0223(12) 0.0224(11) -0.0038(9) 0.0001(9) 0.0000(10) C91 0.0130(10) 0.0213(12) 0.0232(11) -0.0011(9) 0.0002(8) -0.0020(9) C92 0.0204(11) 0.0226(12) 0.0214(11) -0.0035(9) 0.0007(8) -0.0035(9) C93 0.0235(11) 0.0223(12) 0.0201(11) -0.0003(9) 0.0006(9) -0.0025(9) N94 0.0213(9) 0.0190(10) 0.0239(10) -0.0006(8) 0.0006(7) -0.0017(8) C95 0.0226(11) 0.0213(12) 0.0225(11) -0.0035(9) 0.0022(9) -0.0023(9) C96 0.0217(11) 0.0236(12) 0.0206(11) -0.0005(9) 0.0007(8) -0.0010(9) P1 0.0432(4) 0.0269(4) 0.0184(3) -0.0009(2) 0.0057(3) -0.0038(3) F11 0.0397(9) 0.0796(14) 0.0791(13) 0.0556(11) 0.0109(8) 0.0076(9) F12 0.0515(10) 0.0933(16) 0.0646(12) -0.0536(11) -0.0234(9) 0.0249(10) F13 0.0500(9) 0.0397(9) 0.0367(8) 0.0041(7) 0.0166(7) 0.0009(7) F14 0.148(2) 0.0522(12) 0.0867(15) 0.0402(11) 0.0892(15) 0.0543(13) F15 0.0753(14) 0.138(2) 0.0751(14) -0.0730(15) 0.0350(11) -0.0621(14) F16 0.0460(9) 0.0429(9) 0.0300(8) 0.0016(7) 0.0101(6) 0.0003(7) P2 0.0354(4) 0.0281(4) 0.0563(5) 0.0040(3) 0.0175(3) 0.0043(3) F21 0.0409(9) 0.0331(9) 0.0760(12) -0.0010(8) 0.0136(8) 0.0077(7) F22 0.0393(9) 0.0435(10) 0.0716(12) -0.0051(8) 0.0073(8) -0.0007(8) F23 0.0733(13) 0.0541(12) 0.0582(11) 0.0088(9) 0.0271(9) 0.0173(9) F24 0.0487(10) 0.0396(10) 0.0736(12) 0.0084(8) 0.0242(8) 0.0158(8) F25 0.0465(10) 0.0345(9) 0.0891(14) -0.0045(9) 0.0328(9) -0.0064(8) F26 0.0517(10) 0.0424(10) 0.0546(10) 0.0050(8) 0.0153(8) -0.0046(8) N1 0.0675(17) 0.0584(18) 0.0334(13) -0.0132(13) 0.0081(12) 0.0001(14) C1 0.0514(17) 0.0442(17) 0.0253(13) -0.0004(13) 0.0036(12) -0.0106(14) C2 0.071(2) 0.0379(17) 0.0445(17) -0.0100(14) 0.0077(15) -0.0051(15) N2 0.0655(18) 0.0577(18) 0.0454(15) 0.0008(13) 0.0136(13) -0.0111(15) C3 0.0559(19) 0.0496(19) 0.0366(16) -0.0001(13) 0.0034(14) -0.0070(16) C4 0.054(2) 0.076(3) 0.058(2) -0.0035(18) 0.0061(15) -0.0150(18) N3 0.0475(15) 0.0551(17) 0.0389(14) -0.0013(12) -0.0018(11) 0.0043(13) C5 0.0462(16) 0.0302(14) 0.0266(13) -0.0005(11) -0.0031(11) -0.0024(12) C6 0.0500(17) 0.0324(15) 0.0453(17) -0.0065(12) 0.0042(13) 0.0005(13) N4 0.092(3) 0.084(3) 0.077(2) -0.0001(19) 0.026(2) -0.013(2) C7 0.091(3) 0.052(2) 0.0402(18) 0.0013(15) 0.0076(18) 0.001(2) C8 0.082(3) 0.058(2) 0.065(2) 0.0078(18) -0.0096(19) -0.003(2) N5 0.075(2) 0.092(3) 0.085(2) -0.047(2) 0.0070(18) -0.008(2) C9 0.068(2) 0.058(2) 0.0444(18) -0.0185(16) 0.0070(16) -0.0117(19) C10 0.086(3) 0.063(2) 0.0444(19) -0.0075(16) -0.0053(17) 0.016(2) O1W 0.0303(9) 0.0419(11) 0.0252(9) -0.0096(7) 0.0023(7) -0.0030(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 O11 1.369(3) . ? C11 C16 1.384(4) . ? C11 C12 1.388(3) . ? C12 C13 1.391(4) . ? C12 H12 0.9300 . ? C13 O31 1.368(3) . ? C13 C14 1.382(4) . ? C14 C15 1.395(3) . ? C14 H14 0.9300 . ? C15 O51 1.366(3) . ? C15 C16 1.375(4) . ? C16 H16 0.9300 . ? C21 O15 1.364(3) . ? C21 C22 1.385(3) . ? C21 C26 1.395(3) . ? C22 C23 1.390(3) . ? C22 H22 0.9300 . ? C23 O35 1.368(3) . ? C23 C24 1.380(3) . ? C24 C25 1.392(3) . ? C24 H24 0.9300 . ? C25 O55 1.363(3) . ? C25 C26 1.386(3) . ? C26 H26 0.9300 . ? O11 C31 1.423(3) . ? C31 C32 1.497(4) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 O12 1.431(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? O12 C33 1.422(3) . ? C33 C34 1.497(4) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 O13 1.421(3) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? O13 C35 1.413(3) . ? C35 C36 1.489(4) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 O14 1.420(3) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? O14 C37 1.422(3) . ? C37 C38 1.488(3) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 O15 1.438(3) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? O31 C41 1.427(3) . ? C41 C42 1.493(3) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 O32 1.424(3) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? O32 C43 1.423(3) . ? C43 C44 1.495(4) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 O33 1.412(3) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? O33 C45 1.425(3) . ? C45 C46 1.496(3) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 O34 1.427(3) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? O34 C47 1.427(3) . ? C47 C48 1.492(3) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 O35 1.438(3) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? O51 C51 1.428(3) . ? C51 C52 1.505(4) . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 O52 1.410(4) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? O52 C53 1.441(3) . ? C53 C54 1.514(4) . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C54 O53 1.398(3) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? O53 C55 1.441(3) . ? C55 C56 1.484(4) . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C56 O54 1.390(3) . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? O54 C57 1.453(3) . ? C57 C58 1.472(4) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C58 O55 1.436(3) . ? C58 H58A 0.9700 . ? C58 H58B 0.9700 . ? C60 N94 1.493(3) . ? C60 C64 1.507(3) . ? C60 H60A 0.9700 . ? C60 H60B 0.9700 . ? C61 C66 1.391(3) . ? C61 C62 1.397(3) . ? C61 C71 1.482(3) . ? C62 C63 1.396(3) . ? C62 H62 0.9300 . ? C63 C64 1.388(3) . ? C63 H63 0.9300 . ? C64 C65 1.390(3) . ? C65 C66 1.383(3) . ? C65 H65 0.9300 . ? C66 H66 0.9300 . ? C71 C76 1.398(3) . ? C71 C72 1.400(3) . ? C72 C73 1.386(3) . ? C72 H72 0.9300 . ? C73 C74 1.385(3) . ? C73 H73 0.9300 . ? C74 C75 1.401(3) . ? C74 C80 1.505(3) . ? C75 C76 1.384(3) . ? C75 H75 0.9300 . ? C76 H76 0.9300 . ? C80 N84 1.495(3) . ? C80 H80A 0.9700 . ? C80 H80B 0.9700 . ? C81 C86 1.390(3) . ? C81 C82 1.399(3) . ? C81 C91 1.487(3) 3_666 ? C82 C83 1.371(3) . ? C82 H82 0.9300 . ? C83 N84 1.342(3) . ? C83 H83 0.9300 . ? N84 C85 1.347(3) . ? C85 C86 1.373(3) . ? C85 H85 0.9300 . ? C86 H86 0.9300 . ? C91 C96 1.389(3) . ? C91 C92 1.401(3) . ? C91 C81 1.487(3) 3_666 ? C92 C93 1.363(3) . ? C92 H92 0.9300 . ? C93 N94 1.354(3) . ? C93 H93 0.9300 . ? N94 C95 1.338(3) . ? C95 C96 1.372(3) . ? C95 H95 0.9300 . ? C96 H96 0.9300 . ? P1 F15 1.5688(19) . ? P1 F11 1.5694(17) . ? P1 F12 1.5707(17) . ? P1 F14 1.5719(19) . ? P1 F16 1.5962(16) . ? P1 F13 1.6046(16) . ? P2 F23 1.586(2) . ? P2 F22 1.5894(18) . ? P2 F21 1.5901(17) . ? P2 F25 1.5937(18) . ? P2 F26 1.5973(18) . ? P2 F24 1.6051(17) . ? N1 C1 1.132(4) . ? C1 C2 1.451(4) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? N2 C3 1.139(4) . ? C3 C4 1.464(4) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? N3 C5 1.145(3) . ? C5 C6 1.437(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? N4 C7 1.145(5) . ? C7 C8 1.462(6) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N5 C9 1.157(5) . ? C9 C10 1.435(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? O1W H1A 0.9446 . ? O1W H1B 0.9181 . ? 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 O11 C11 C16 114.9(2) . . ? O11 C11 C12 123.9(2) . . ? C16 C11 C12 121.2(2) . . ? C11 C12 C13 118.6(2) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? O31 C13 C14 123.9(2) . . ? O31 C13 C12 114.7(2) . . ? C14 C13 C12 121.4(2) . . ? C13 C14 C15 118.3(2) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? O51 C15 C16 114.9(2) . . ? O51 C15 C14 123.5(2) . . ? C16 C15 C14 121.6(2) . . ? C15 C16 C11 118.9(2) . . ? C15 C16 H16 120.5 . . ? C11 C16 H16 120.5 . . ? O15 C21 C22 116.05(19) . . ? O15 C21 C26 122.63(19) . . ? C22 C21 C26 121.3(2) . . ? C21 C22 C23 119.1(2) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? O35 C23 C24 124.2(2) . . ? O35 C23 C22 114.98(19) . . ? C24 C23 C22 120.9(2) . . ? C23 C24 C25 119.0(2) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? O55 C25 C26 123.6(2) . . ? O55 C25 C24 114.8(2) . . ? C26 C25 C24 121.5(2) . . ? C25 C26 C21 118.1(2) . . ? C25 C26 H26 120.9 . . ? C21 C26 H26 120.9 . . ? C11 O11 C31 117.55(19) . . ? O11 C31 C32 108.6(2) . . ? O11 C31 H31A 110.0 . . ? C32 C31 H31A 110.0 . . ? O11 C31 H31B 110.0 . . ? C32 C31 H31B 110.0 . . ? H31A C31 H31B 108.4 . . ? O12 C32 C31 109.8(2) . . ? O12 C32 H32A 109.7 . . ? C31 C32 H32A 109.7 . . ? O12 C32 H32B 109.7 . . ? C31 C32 H32B 109.7 . . ? H32A C32 H32B 108.2 . . ? C33 O12 C32 110.82(19) . . ? O12 C33 C34 110.1(2) . . ? O12 C33 H33A 109.6 . . ? C34 C33 H33A 109.6 . . ? O12 C33 H33B 109.6 . . ? C34 C33 H33B 109.6 . . ? H33A C33 H33B 108.2 . . ? O13 C34 C33 110.2(2) . . ? O13 C34 H34A 109.6 . . ? C33 C34 H34A 109.6 . . ? O13 C34 H34B 109.6 . . ? C33 C34 H34B 109.6 . . ? H34A C34 H34B 108.1 . . ? C35 O13 C34 110.77(18) . . ? O13 C35 C36 110.6(2) . . ? O13 C35 H35A 109.5 . . ? C36 C35 H35A 109.5 . . ? O13 C35 H35B 109.5 . . ? C36 C35 H35B 109.5 . . ? H35A C35 H35B 108.1 . . ? O14 C36 C35 109.3(2) . . ? O14 C36 H36A 109.8 . . ? C35 C36 H36A 109.8 . . ? O14 C36 H36B 109.8 . . ? C35 C36 H36B 109.8 . . ? H36A C36 H36B 108.3 . . ? C36 O14 C37 112.13(18) . . ? O14 C37 C38 108.26(19) . . ? O14 C37 H37A 110.0 . . ? C38 C37 H37A 110.0 . . ? O14 C37 H37B 110.0 . . ? C38 C37 H37B 110.0 . . ? H37A C37 H37B 108.4 . . ? O15 C38 C37 108.38(18) . . ? O15 C38 H38A 110.0 . . ? C37 C38 H38A 110.0 . . ? O15 C38 H38B 110.0 . . ? C37 C38 H38B 110.0 . . ? H38A C38 H38B 108.4 . . ? C21 O15 C38 116.69(17) . . ? C13 O31 C41 117.24(19) . . ? O31 C41 C42 108.0(2) . . ? O31 C41 H41A 110.1 . . ? C42 C41 H41A 110.1 . . ? O31 C41 H41B 110.1 . . ? C42 C41 H41B 110.1 . . ? H41A C41 H41B 108.4 . . ? O32 C42 C41 108.67(19) . . ? O32 C42 H42A 110.0 . . ? C41 C42 H42A 110.0 . . ? O32 C42 H42B 110.0 . . ? C41 C42 H42B 110.0 . . ? H42A C42 H42B 108.3 . . ? C43 O32 C42 112.91(18) . . ? O32 C43 C44 107.63(19) . . ? O32 C43 H43A 110.2 . . ? C44 C43 H43A 110.2 . . ? O32 C43 H43B 110.2 . . ? C44 C43 H43B 110.2 . . ? H43A C43 H43B 108.5 . . ? O33 C44 C43 109.0(2) . . ? O33 C44 H44A 109.9 . . ? C43 C44 H44A 109.9 . . ? O33 C44 H44B 109.9 . . ? C43 C44 H44B 109.9 . . ? H44A C44 H44B 108.3 . . ? C44 O33 C45 112.27(19) . . ? O33 C45 C46 109.1(2) . . ? O33 C45 H45A 109.9 . . ? C46 C45 H45A 109.9 . . ? O33 C45 H45B 109.9 . . ? C46 C45 H45B 109.9 . . ? H45A C45 H45B 108.3 . . ? O34 C46 C45 109.68(19) . . ? O34 C46 H46A 109.7 . . ? C45 C46 H46A 109.7 . . ? O34 C46 H46B 109.7 . . ? C45 C46 H46B 109.7 . . ? H46A C46 H46B 108.2 . . ? C47 O34 C46 110.03(17) . . ? O34 C47 C48 112.19(19) . . ? O34 C47 H47A 109.2 . . ? C48 C47 H47A 109.2 . . ? O34 C47 H47B 109.2 . . ? C48 C47 H47B 109.2 . . ? H47A C47 H47B 107.9 . . ? O35 C48 C47 108.6(2) . . ? O35 C48 H48A 110.0 . . ? C47 C48 H48A 110.0 . . ? O35 C48 H48B 110.0 . . ? C47 C48 H48B 110.0 . . ? H48A C48 H48B 108.3 . . ? C23 O35 C48 117.74(17) . . ? C15 O51 C51 117.6(2) . . ? O51 C51 C52 107.7(2) . . ? O51 C51 H51A 110.2 . . ? C52 C51 H51A 110.2 . . ? O51 C51 H51B 110.2 . . ? C52 C51 H51B 110.2 . . ? H51A C51 H51B 108.5 . . ? O52 C52 C51 109.7(2) . . ? O52 C52 H52A 109.7 . . ? C51 C52 H52A 109.7 . . ? O52 C52 H52B 109.7 . . ? C51 C52 H52B 109.7 . . ? H52A C52 H52B 108.2 . . ? C52 O52 C53 111.7(2) . . ? O52 C53 C54 108.8(2) . . ? O52 C53 H53A 109.9 . . ? C54 C53 H53A 109.9 . . ? O52 C53 H53B 109.9 . . ? C54 C53 H53B 109.9 . . ? H53A C53 H53B 108.3 . . ? O53 C54 C53 108.5(2) . . ? O53 C54 H54A 110.0 . . ? C53 C54 H54A 110.0 . . ? O53 C54 H54B 110.0 . . ? C53 C54 H54B 110.0 . . ? H54A C54 H54B 108.4 . . ? C54 O53 C55 112.2(2) . . ? O53 C55 C56 115.5(2) . . ? O53 C55 H55A 108.4 . . ? C56 C55 H55A 108.4 . . ? O53 C55 H55B 108.4 . . ? C56 C55 H55B 108.4 . . ? H55A C55 H55B 107.5 . . ? O54 C56 C55 108.8(2) . . ? O54 C56 H56A 109.9 . . ? C55 C56 H56A 109.9 . . ? O54 C56 H56B 109.9 . . ? C55 C56 H56B 109.9 . . ? H56A C56 H56B 108.3 . . ? C56 O54 C57 113.97(19) . . ? O54 C57 C58 111.0(2) . . ? O54 C57 H57A 109.4 . . ? C58 C57 H57A 109.4 . . ? O54 C57 H57B 109.4 . . ? C58 C57 H57B 109.4 . . ? H57A C57 H57B 108.0 . . ? O55 C58 C57 111.9(2) . . ? O55 C58 H58A 109.2 . . ? C57 C58 H58A 109.2 . . ? O55 C58 H58B 109.2 . . ? C57 C58 H58B 109.2 . . ? H58A C58 H58B 107.9 . . ? C25 O55 C58 119.03(18) . . ? N94 C60 C64 108.54(18) . . ? N94 C60 H60A 110.0 . . ? C64 C60 H60A 110.0 . . ? N94 C60 H60B 110.0 . . ? C64 C60 H60B 110.0 . . ? H60A C60 H60B 108.4 . . ? C66 C61 C62 117.8(2) . . ? C66 C61 C71 120.34(19) . . ? C62 C61 C71 121.67(19) . . ? C63 C62 C61 121.0(2) . . ? C63 C62 H62 119.5 . . ? C61 C62 H62 119.5 . . ? C64 C63 C62 120.4(2) . . ? C64 C63 H63 119.8 . . ? C62 C63 H63 119.8 . . ? C63 C64 C65 118.4(2) . . ? C63 C64 C60 122.0(2) . . ? C65 C64 C60 119.4(2) . . ? C66 C65 C64 121.2(2) . . ? C66 C65 H65 119.4 . . ? C64 C65 H65 119.4 . . ? C65 C66 C61 121.0(2) . . ? C65 C66 H66 119.5 . . ? C61 C66 H66 119.5 . . ? C76 C71 C72 117.5(2) . . ? C76 C71 C61 122.43(19) . . ? C72 C71 C61 119.96(19) . . ? C73 C72 C71 121.2(2) . . ? C73 C72 H72 119.4 . . ? C71 C72 H72 119.4 . . ? C74 C73 C72 120.8(2) . . ? C74 C73 H73 119.6 . . ? C72 C73 H73 119.6 . . ? C73 C74 C75 118.7(2) . . ? C73 C74 C80 119.8(2) . . ? C75 C74 C80 121.4(2) . . ? C76 C75 C74 120.3(2) . . ? C76 C75 H75 119.8 . . ? C74 C75 H75 119.8 . . ? C75 C76 C71 121.4(2) . . ? C75 C76 H76 119.3 . . ? C71 C76 H76 119.3 . . ? N84 C80 C74 109.97(17) . . ? N84 C80 H80A 109.7 . . ? C74 C80 H80A 109.7 . . ? N84 C80 H80B 109.7 . . ? C74 C80 H80B 109.7 . . ? H80A C80 H80B 108.2 . . ? C86 C81 C82 117.2(2) . . ? C86 C81 C91 122.7(2) . 3_666 ? C82 C81 C91 120.09(19) . 3_666 ? C83 C82 C81 119.8(2) . . ? C83 C82 H82 120.1 . . ? C81 C82 H82 120.1 . . ? N84 C83 C82 121.6(2) . . ? N84 C83 H83 119.2 . . ? C82 C83 H83 119.2 . . ? C83 N84 C85 119.96(19) . . ? C83 N84 C80 118.95(18) . . ? C85 N84 C80 121.04(18) . . ? N84 C85 C86 120.6(2) . . ? N84 C85 H85 119.7 . . ? C86 C85 H85 119.7 . . ? C85 C86 C81 120.8(2) . . ? C85 C86 H86 119.6 . . ? C81 C86 H86 119.6 . . ? C96 C91 C92 117.1(2) . . ? C96 C91 C81 121.75(19) . 3_666 ? C92 C91 C81 121.1(2) . 3_666 ? C93 C92 C91 120.3(2) . . ? C93 C92 H92 119.8 . . ? C91 C92 H92 119.8 . . ? N94 C93 C92 120.7(2) . . ? N94 C93 H93 119.6 . . ? C92 C93 H93 119.6 . . ? C95 N94 C93 120.53(19) . . ? C95 N94 C60 120.97(19) . . ? C93 N94 C60 118.38(18) . . ? N94 C95 C96 120.5(2) . . ? N94 C95 H95 119.8 . . ? C96 C95 H95 119.8 . . ? C95 C96 C91 120.8(2) . . ? C95 C96 H96 119.6 . . ? C91 C96 H96 119.6 . . ? F15 P1 F11 89.74(15) . . ? F15 P1 F12 179.73(16) . . ? F11 P1 F12 90.53(13) . . ? F15 P1 F14 89.69(16) . . ? F11 P1 F14 179.24(14) . . ? F12 P1 F14 90.05(14) . . ? F15 P1 F16 90.06(10) . . ? F11 P1 F16 90.73(9) . . ? F12 P1 F16 89.95(10) . . ? F14 P1 F16 89.76(10) . . ? F15 P1 F13 90.84(10) . . ? F11 P1 F13 89.45(9) . . ? F12 P1 F13 89.15(10) . . ? F14 P1 F13 90.07(9) . . ? F16 P1 F13 179.08(9) . . ? F23 P2 F22 90.87(11) . . ? F23 P2 F21 90.80(10) . . ? F22 P2 F21 90.58(9) . . ? F23 P2 F25 89.81(11) . . ? F22 P2 F25 178.73(10) . . ? F21 P2 F25 90.48(9) . . ? F23 P2 F26 178.69(10) . . ? F22 P2 F26 90.03(10) . . ? F21 P2 F26 90.14(10) . . ? F25 P2 F26 89.27(10) . . ? F23 P2 F24 89.99(10) . . ? F22 P2 F24 89.20(10) . . ? F21 P2 F24 179.19(11) . . ? F25 P2 F24 89.73(10) . . ? F26 P2 F24 89.08(10) . . ? N1 C1 C2 178.7(3) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 178.7(4) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 C6 178.7(3) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 C8 178.7(5) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 C10 178.2(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? H1A O1W H1B 99.4 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.555 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.059 _publ_section_exptl_refinement ; The H atoms of the water were located in a difference Fourier map and refined in its as-found position, with a fixed isotropic displacement parameter of 0.08 \%A^2^. Other H atoms were placed in calculated positions, with C---H = 0.93 - 0.97 \%A, and included in the final cycles of refinement in a riding model, with U~iso~(H) = 1.2U~eq~ or 1.5U~eq~ of the carrier atoms. ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350. Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokjo, Japan. Rigaku.MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Sheldrick, G. M. (1997). SHELXL-97. University of G\"ottingen, Germany. ; # SQUEEZE RESULTS (APPEND TO CIF) # 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 1.000 -0.069 0.250 617 80 ' ' 2 1.000 -0.026 0.750 617 80 ' ' 3 0.437 0.097 0.236 7 0 ' ' 4 0.437 0.403 0.736 7 0 ' ' 5 0.563 0.597 0.264 7 0 ' ' 6 0.563 0.903 0.764 7 0 ' ' _platon_squeeze_details ; The PLATON/SQUEEZE was used to remove the contributions of disordered water molecules, leaving two large voids at the coordinates of (1.000, -0.069, 0.250) and (1.000, -0.026, 0.750) with the same volumes of 617 \%A^3^. 80 electrons were effectively removed in each void, which corresponds with 16 water molecules in the unit cell, or 4 per asymmetric unit. After L.S.-convergence, a proper final FCF file was produced by running PLATON/CALC FCF. ;