# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Stoddart, J.' _publ_contact_author_email stoddart@northwestern.edu _publ_section_title ; Arranging pseudorotaxanes octahedrally around [60]fullerene ; loop_ _publ_author_name S.K.Dey F.Beuerle M.A.Olson J.F.Stoddart # Attachment '- Dey_Pseudorotaxane.cif' data_n0240 _database_code_depnum_ccdc_archive 'CCDC 776151' #TrackingRef '- Dey_Pseudorotaxane.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H30 O10, C14 H16 N, F6 P' _chemical_formula_sum 'C35 H46 F6 N O10 P' _chemical_formula_weight 785.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 15.7752(6) _cell_length_b 13.5842(5) _cell_length_c 17.3986(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.141(3) _cell_angle_gamma 90.00 _cell_volume 3645.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6210 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 58.37 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 1.455 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5110 _exptl_absorpt_correction_T_max 0.8646 _exptl_absorpt_process_details Face-indexed _exptl_special_details ; A face-indexed absorption correction was applied to the raw data. An inter- frame scaling correction was subsequently applied via SADABS (Bruker). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18040 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 58.55 _reflns_number_total 5080 _reflns_number_gt 4117 _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^)+(0.0490P)^2^+1.9825P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5080 _refine_ls_number_parameters 486 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 P1 P 0.25391(4) 0.22722(4) 0.10723(4) 0.02907(18) Uani 1 1 d . . . F1 F 0.34933(9) 0.23060(10) 0.16118(8) 0.0380(4) Uani 1 1 d . . . F2 F 0.27686(10) 0.31723(12) 0.05734(10) 0.0584(5) Uani 1 1 d . . . F3 F 0.28618(10) 0.15095(12) 0.04991(9) 0.0499(4) Uani 1 1 d . . . F4 F 0.15802(9) 0.22329(11) 0.05409(9) 0.0438(4) Uani 1 1 d . . . F5 F 0.22959(9) 0.13752(10) 0.15866(8) 0.0395(4) Uani 1 1 d . . . F6 F 0.22100(10) 0.30140(11) 0.16643(10) 0.0495(4) Uani 1 1 d . . . O1 O 1.03685(12) 0.55102(13) 0.08406(11) 0.0438(5) Uani 1 1 d . . . O2 O 0.95127(10) 0.44261(11) 0.12765(10) 0.0321(4) Uani 1 1 d . . . O3 O 0.95531(10) 0.23854(11) 0.17785(10) 0.0317(4) Uani 1 1 d . . . O4 O 0.88941(9) 0.04984(11) 0.14221(9) 0.0270(4) Uani 1 1 d . . . O5 O 0.70866(9) 0.00100(10) 0.11634(9) 0.0245(4) Uani 1 1 d . . . O6 O 0.57621(9) 0.11728(10) 0.06704(9) 0.0238(4) Uani 1 1 d . . . O7 O 0.56932(10) 0.33425(10) 0.05456(9) 0.0263(4) Uani 1 1 d . . . O8 O 0.60052(10) 0.52861(11) 0.11916(9) 0.0320(4) Uani 1 1 d . . . O9 O 0.76679(11) 0.58569(12) 0.10559(10) 0.0338(4) Uani 1 1 d . . . O10 O 0.86939(11) 0.70279(12) 0.12418(10) 0.0373(4) Uani 1 1 d . . . N1 N 0.75674(15) 0.20900(14) 0.11851(12) 0.0239(4) Uani 1 1 d . . . H1AN H 0.8000(18) 0.169(2) 0.1291(15) 0.036(8) Uiso 1 1 d . . . H1BN H 0.7104(17) 0.1811(17) 0.1038(14) 0.023(7) Uiso 1 1 d . . . C1 C 0.88249(16) 0.56436(17) 0.04096(14) 0.0308(6) Uani 1 1 d . . . H1A H 0.8427 0.5109 0.0177 0.037 Uiso 1 1 calc R . . H1B H 0.8942 0.6059 -0.0024 0.037 Uiso 1 1 calc R . . C2 C 0.96553(16) 0.52108(17) 0.08548(15) 0.0303(6) Uani 1 1 d . . . C3 C 1.02841(15) 0.39547(18) 0.17356(15) 0.0341(6) Uani 1 1 d . . . H3A H 1.0653 0.4446 0.2070 0.041 Uiso 1 1 calc R . . H3B H 1.0626 0.3648 0.1383 0.041 Uiso 1 1 calc R . . C4 C 0.99832(16) 0.31871(17) 0.22349(15) 0.0335(6) Uani 1 1 d . . . H4A H 1.0489 0.2931 0.2619 0.040 Uiso 1 1 calc R . . H4B H 0.9582 0.3492 0.2533 0.040 Uiso 1 1 calc R . . C5 C 1.01145(15) 0.15661(17) 0.17631(16) 0.0354(6) Uani 1 1 d . . . H5A H 1.0273 0.1266 0.2292 0.042 Uiso 1 1 calc R . . H5B H 1.0653 0.1787 0.1609 0.042 Uiso 1 1 calc R . . C6 C 0.96590(15) 0.08245(18) 0.11844(15) 0.0320(6) Uani 1 1 d . . . H6A H 0.9504 0.1124 0.0655 0.038 Uiso 1 1 calc R . . H6B H 1.0047 0.0258 0.1160 0.038 Uiso 1 1 calc R . . C7 C 0.85136(15) -0.03447(16) 0.09863(14) 0.0275(5) Uani 1 1 d . . . H7A H 0.8953 -0.0871 0.1015 0.033 Uiso 1 1 calc R . . H7B H 0.8304 -0.0165 0.0427 0.033 Uiso 1 1 calc R . . C8 C 0.77772(14) -0.07049(16) 0.13219(14) 0.0267(5) Uani 1 1 d . . . H8A H 0.7569 -0.1345 0.1082 0.032 Uiso 1 1 calc R . . H8B H 0.7969 -0.0801 0.1896 0.032 Uiso 1 1 calc R . . C9 C 0.63185(14) -0.02704(16) 0.13493(13) 0.0219(5) Uani 1 1 d . . . C10 C 0.62212(15) -0.11005(16) 0.17868(13) 0.0250(5) Uani 1 1 d . . . H10 H 0.6712 -0.1491 0.2006 0.030 Uiso 1 1 calc R . . C11 C 0.54083(15) -0.13613(17) 0.19043(13) 0.0275(5) Uani 1 1 d . . . H11 H 0.5344 -0.1931 0.2204 0.033 Uiso 1 1 calc R . . C12 C 0.46921(15) -0.07979(17) 0.15877(14) 0.0281(5) Uani 1 1 d . . . H12 H 0.4133 -0.0994 0.1652 0.034 Uiso 1 1 calc R . . C13 C 0.47881(15) 0.00577(16) 0.11735(13) 0.0258(5) Uani 1 1 d . . . H13 H 0.4297 0.0454 0.0967 0.031 Uiso 1 1 calc R . . C14 C 0.55961(14) 0.03312(15) 0.10626(13) 0.0231(5) Uani 1 1 d . . . C15 C 0.50047(14) 0.17355(16) 0.03046(14) 0.0257(5) Uani 1 1 d . . . H15A H 0.4662 0.1912 0.0700 0.031 Uiso 1 1 calc R . . H15B H 0.4633 0.1341 -0.0113 0.031 Uiso 1 1 calc R . . C16 C 0.53078(15) 0.26510(16) -0.00403(14) 0.0267(5) Uani 1 1 d . . . H16A H 0.5736 0.2468 -0.0358 0.032 Uiso 1 1 calc R . . H16B H 0.4808 0.2965 -0.0395 0.032 Uiso 1 1 calc R . . C17 C 0.50554(15) 0.39221(16) 0.08207(15) 0.0291(6) Uani 1 1 d . . . H17A H 0.4636 0.3486 0.1005 0.035 Uiso 1 1 calc R . . H17B H 0.4734 0.4337 0.0389 0.035 Uiso 1 1 calc R . . C18 C 0.55103(16) 0.45561(16) 0.14807(14) 0.0295(6) Uani 1 1 d . . . H18A H 0.5079 0.4875 0.1739 0.035 Uiso 1 1 calc R . . H18B H 0.5897 0.4146 0.1877 0.035 Uiso 1 1 calc R . . C19 C 0.65878(16) 0.57560(19) 0.18191(15) 0.0350(6) Uani 1 1 d . . . H19A H 0.6947 0.5256 0.2152 0.042 Uiso 1 1 calc R . . H19B H 0.6257 0.6125 0.2150 0.042 Uiso 1 1 calc R . . C20 C 0.71538(16) 0.64405(18) 0.14913(16) 0.0358(6) Uani 1 1 d . . . H20A H 0.6797 0.6924 0.1138 0.043 Uiso 1 1 calc R . . H20B H 0.7538 0.6804 0.1921 0.043 Uiso 1 1 calc R . . C21 C 0.84007(15) 0.62616(17) 0.09501(14) 0.0285(6) Uani 1 1 d . . . C22 C 0.77249(15) 0.27766(16) 0.05587(13) 0.0246(5) Uani 1 1 d . . . H22A H 0.8194 0.3242 0.0786 0.029 Uiso 1 1 calc R . . H22B H 0.7193 0.3163 0.0356 0.029 Uiso 1 1 calc R . . C23 C 0.79764(14) 0.22217(16) -0.01101(13) 0.0240(5) Uani 1 1 d . . . C24 C 0.74890(15) 0.14225(16) -0.04574(14) 0.0274(5) Uani 1 1 d . . . H24A H 0.6976 0.1241 -0.0289 0.033 Uiso 1 1 calc R . . C25 C 0.77499(16) 0.08921(17) -0.10467(14) 0.0308(6) Uani 1 1 d . . . H25 H 0.7419 0.0343 -0.1278 0.037 Uiso 1 1 calc R . . C26 C 0.84922(16) 0.11606(18) -0.12981(14) 0.0330(6) Uani 1 1 d . . . H26 H 0.8673 0.0792 -0.1699 0.040 Uiso 1 1 calc R . . C27 C 0.89728(17) 0.19656(19) -0.09664(15) 0.0362(6) Uani 1 1 d . . . H27 H 0.9477 0.2157 -0.1145 0.043 Uiso 1 1 calc R . . C28 C 0.87134(16) 0.24895(17) -0.03717(14) 0.0310(6) Uani 1 1 d . . . H28A H 0.9045 0.3038 -0.0141 0.037 Uiso 1 1 calc R . . C29 C 0.74762(15) 0.26070(16) 0.19220(14) 0.0260(5) Uani 1 1 d . . . H29A H 0.7041 0.3139 0.1789 0.031 Uiso 1 1 calc R . . H29B H 0.8037 0.2912 0.2169 0.031 Uiso 1 1 calc R . . C30 C 0.72006(15) 0.19109(16) 0.24999(13) 0.0247(5) Uani 1 1 d . . . C31 C 0.77755(15) 0.12029(17) 0.28909(14) 0.0294(6) Uani 1 1 d . . . H31 H 0.8346 0.1161 0.2795 0.035 Uiso 1 1 calc R . . C32 C 0.75199(16) 0.05632(18) 0.34160(14) 0.0335(6) Uani 1 1 d . . . H32 H 0.7909 0.0072 0.3669 0.040 Uiso 1 1 calc R . . C33 C 0.67008(17) 0.06367(17) 0.35742(15) 0.0338(6) Uani 1 1 d . . . H33 H 0.6530 0.0204 0.3943 0.041 Uiso 1 1 calc R . . C34 C 0.61296(16) 0.13418(17) 0.31958(15) 0.0341(6) Uani 1 1 d . . . H34 H 0.5568 0.1399 0.3308 0.041 Uiso 1 1 calc R . . C35 C 0.63789(15) 0.19654(17) 0.26521(14) 0.0294(6) Uani 1 1 d . . . H35 H 0.5979 0.2435 0.2382 0.035 Uiso 1 1 calc 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 P1 0.0311(4) 0.0254(3) 0.0298(4) 0.0021(3) 0.0043(3) 0.0019(3) F1 0.0333(8) 0.0415(8) 0.0362(8) -0.0009(7) 0.0007(6) 0.0020(6) F2 0.0509(10) 0.0579(11) 0.0609(11) 0.0317(9) -0.0006(8) -0.0116(8) F3 0.0462(9) 0.0655(11) 0.0389(9) -0.0185(8) 0.0113(7) 0.0017(8) F4 0.0345(8) 0.0468(9) 0.0448(9) 0.0098(7) -0.0034(7) -0.0020(7) F5 0.0471(9) 0.0317(8) 0.0390(9) 0.0066(6) 0.0078(7) -0.0002(6) F6 0.0466(10) 0.0369(8) 0.0654(11) -0.0169(8) 0.0126(8) 0.0040(7) O1 0.0359(12) 0.0384(11) 0.0572(13) 0.0110(9) 0.0103(9) -0.0043(9) O2 0.0299(10) 0.0270(9) 0.0377(10) 0.0092(8) 0.0030(7) -0.0014(7) O3 0.0290(9) 0.0243(9) 0.0410(10) 0.0031(7) 0.0055(8) -0.0002(7) O4 0.0240(9) 0.0237(9) 0.0346(9) -0.0004(7) 0.0089(7) -0.0015(7) O5 0.0225(9) 0.0179(8) 0.0334(9) 0.0013(7) 0.0064(7) 0.0011(6) O6 0.0241(9) 0.0182(8) 0.0292(9) 0.0016(7) 0.0058(7) 0.0014(6) O7 0.0279(9) 0.0191(8) 0.0332(9) -0.0033(7) 0.0093(7) 0.0009(7) O8 0.0384(10) 0.0265(9) 0.0308(9) -0.0027(7) 0.0063(8) -0.0063(7) O9 0.0377(10) 0.0260(9) 0.0407(10) -0.0058(8) 0.0149(8) -0.0030(7) O10 0.0428(11) 0.0301(10) 0.0386(10) -0.0064(8) 0.0075(8) -0.0058(8) N1 0.0244(13) 0.0198(10) 0.0282(11) 0.0001(9) 0.0072(9) -0.0012(10) C1 0.0355(15) 0.0265(13) 0.0318(14) 0.0028(11) 0.0103(11) 0.0019(11) C2 0.0308(15) 0.0240(13) 0.0375(15) -0.0023(11) 0.0105(11) -0.0022(11) C3 0.0267(14) 0.0316(14) 0.0411(15) 0.0061(12) 0.0004(11) -0.0003(11) C4 0.0358(15) 0.0293(14) 0.0347(15) 0.0041(11) 0.0055(11) -0.0001(11) C5 0.0229(13) 0.0290(14) 0.0540(17) 0.0067(12) 0.0076(12) 0.0014(11) C6 0.0248(14) 0.0289(13) 0.0451(16) 0.0058(12) 0.0142(12) 0.0044(10) C7 0.0278(14) 0.0201(12) 0.0342(14) -0.0001(10) 0.0057(11) 0.0051(10) C8 0.0248(13) 0.0192(12) 0.0348(14) 0.0013(10) 0.0033(10) 0.0037(10) C9 0.0223(13) 0.0210(12) 0.0220(12) -0.0055(10) 0.0038(10) -0.0029(9) C10 0.0306(14) 0.0197(12) 0.0240(12) -0.0014(10) 0.0042(10) 0.0004(10) C11 0.0334(14) 0.0240(12) 0.0256(13) 0.0012(10) 0.0069(10) -0.0036(10) C12 0.0275(13) 0.0281(13) 0.0302(14) -0.0025(11) 0.0095(10) -0.0051(10) C13 0.0266(14) 0.0237(12) 0.0272(13) -0.0029(10) 0.0056(10) 0.0019(10) C14 0.0292(14) 0.0164(11) 0.0234(12) -0.0029(10) 0.0049(10) -0.0013(9) C15 0.0257(13) 0.0201(12) 0.0302(13) -0.0014(10) 0.0035(10) 0.0026(10) C16 0.0305(14) 0.0231(12) 0.0267(13) -0.0019(10) 0.0065(10) 0.0018(10) C17 0.0322(14) 0.0201(12) 0.0380(14) -0.0001(11) 0.0142(11) 0.0024(10) C18 0.0352(14) 0.0226(12) 0.0335(14) 0.0025(11) 0.0137(11) 0.0042(10) C19 0.0370(15) 0.0357(14) 0.0335(14) -0.0122(12) 0.0100(12) -0.0049(12) C20 0.0372(15) 0.0302(14) 0.0422(16) -0.0103(12) 0.0133(12) 0.0015(11) C21 0.0288(14) 0.0266(14) 0.0286(14) 0.0013(11) 0.0024(11) 0.0015(11) C22 0.0283(13) 0.0179(12) 0.0281(13) 0.0026(10) 0.0072(10) -0.0007(9) C23 0.0260(13) 0.0191(12) 0.0269(13) 0.0039(10) 0.0061(10) 0.0037(10) C24 0.0257(13) 0.0254(13) 0.0322(14) 0.0019(11) 0.0083(10) 0.0018(10) C25 0.0386(15) 0.0223(12) 0.0305(14) -0.0009(11) 0.0046(11) 0.0036(11) C26 0.0426(16) 0.0304(14) 0.0286(14) 0.0053(11) 0.0133(12) 0.0126(12) C27 0.0389(16) 0.0387(15) 0.0348(15) 0.0060(12) 0.0168(12) 0.0015(12) C28 0.0345(15) 0.0256(13) 0.0335(14) 0.0026(11) 0.0084(11) -0.0040(11) C29 0.0280(13) 0.0221(12) 0.0291(13) -0.0048(10) 0.0088(10) -0.0017(10) C30 0.0298(14) 0.0206(12) 0.0238(13) -0.0059(10) 0.0061(10) -0.0037(10) C31 0.0255(13) 0.0322(14) 0.0302(13) -0.0003(11) 0.0054(10) -0.0004(11) C32 0.0361(16) 0.0314(14) 0.0307(14) 0.0037(11) 0.0017(11) 0.0000(11) C33 0.0440(17) 0.0279(14) 0.0328(14) -0.0011(11) 0.0153(12) -0.0077(12) C34 0.0337(15) 0.0271(13) 0.0464(16) -0.0060(12) 0.0197(12) -0.0039(11) C35 0.0322(15) 0.0215(12) 0.0359(14) -0.0028(11) 0.0103(11) -0.0005(10) _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 F2 1.5848(16) . ? P1 F3 1.5939(16) . ? P1 F1 1.5984(15) . ? P1 F4 1.5992(15) . ? P1 F6 1.6033(16) . ? P1 F5 1.6054(15) . ? O1 C2 1.201(3) . ? O2 C2 1.340(3) . ? O2 C3 1.456(3) . ? O3 C5 1.426(3) . ? O3 C4 1.432(3) . ? O4 C6 1.426(3) . ? O4 C7 1.434(3) . ? O5 C9 1.372(3) . ? O5 C8 1.442(3) . ? O6 C14 1.384(3) . ? O6 C15 1.448(3) . ? O7 C16 1.425(3) . ? O7 C17 1.437(3) . ? O8 C18 1.418(3) . ? O8 C19 1.422(3) . ? O9 C21 1.327(3) . ? O9 C20 1.456(3) . ? O10 C21 1.207(3) . ? N1 C22 1.494(3) . ? N1 C29 1.495(3) . ? N1 H1AN 0.86(3) . ? N1 H1BN 0.82(3) . ? C1 C2 1.495(3) . ? C1 C21 1.517(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C3 C4 1.497(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.497(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.488(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.387(3) . ? C9 C14 1.406(3) . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.380(3) . ? C11 H11 0.9500 . ? C12 C13 1.392(3) . ? C12 H12 0.9500 . ? C13 C14 1.380(3) . ? C13 H13 0.9500 . ? C15 C16 1.502(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.493(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.484(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C22 C23 1.508(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C28 1.383(3) . ? C23 C24 1.393(3) . ? C24 C25 1.385(3) . ? C24 H24A 0.9500 . ? C25 C26 1.382(3) . ? C25 H25 0.9500 . ? C26 C27 1.386(4) . ? C26 H26 0.9500 . ? C27 C28 1.387(3) . ? C27 H27 0.9500 . ? C28 H28A 0.9500 . ? C29 C30 1.509(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C35 1.379(3) . ? C30 C31 1.397(3) . ? C31 C32 1.381(3) . ? C31 H31 0.9500 . ? C32 C33 1.380(4) . ? C32 H32 0.9500 . ? C33 C34 1.383(4) . ? C33 H33 0.9500 . ? C34 C35 1.387(3) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? 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 F2 P1 F3 91.09(10) . . ? F2 P1 F1 90.24(8) . . ? F3 P1 F1 90.05(8) . . ? F2 P1 F4 90.37(8) . . ? F3 P1 F4 90.24(8) . . ? F1 P1 F4 179.32(9) . . ? F2 P1 F6 90.52(10) . . ? F3 P1 F6 178.38(9) . . ? F1 P1 F6 89.83(8) . . ? F4 P1 F6 89.87(9) . . ? F2 P1 F5 178.85(10) . . ? F3 P1 F5 90.03(9) . . ? F1 P1 F5 90.02(8) . . ? F4 P1 F5 89.37(8) . . ? F6 P1 F5 88.36(8) . . ? C2 O2 C3 115.67(18) . . ? C5 O3 C4 112.35(18) . . ? C6 O4 C7 112.37(17) . . ? C9 O5 C8 115.91(16) . . ? C14 O6 C15 115.37(16) . . ? C16 O7 C17 112.10(17) . . ? C18 O8 C19 110.90(18) . . ? C21 O9 C20 116.32(18) . . ? C22 N1 C29 113.14(17) . . ? C22 N1 H1AN 107.8(17) . . ? C29 N1 H1AN 109.3(17) . . ? C22 N1 H1BN 109.7(17) . . ? C29 N1 H1BN 104.3(17) . . ? H1AN N1 H1BN 113(2) . . ? C2 C1 C21 110.4(2) . . ? C2 C1 H1A 109.6 . . ? C21 C1 H1A 109.6 . . ? C2 C1 H1B 109.6 . . ? C21 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? O1 C2 O2 123.1(2) . . ? O1 C2 C1 125.3(2) . . ? O2 C2 C1 111.5(2) . . ? O2 C3 C4 107.12(19) . . ? O2 C3 H3A 110.3 . . ? C4 C3 H3A 110.3 . . ? O2 C3 H3B 110.3 . . ? C4 C3 H3B 110.3 . . ? H3A C3 H3B 108.5 . . ? O3 C4 C3 112.3(2) . . ? O3 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? O3 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? O3 C5 C6 109.00(19) . . ? O3 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? O3 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? O4 C6 C5 109.3(2) . . ? O4 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? O4 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? O4 C7 C8 109.26(18) . . ? O4 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? O4 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? O5 C8 C7 108.91(18) . . ? O5 C8 H8A 109.9 . . ? C7 C8 H8A 109.9 . . ? O5 C8 H8B 109.9 . . ? C7 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? O5 C9 C10 124.1(2) . . ? O5 C9 C14 116.43(19) . . ? C10 C9 C14 119.5(2) . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C10 120.3(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 120.0(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.1(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 O6 124.6(2) . . ? C13 C14 C9 119.8(2) . . ? O6 C14 C9 115.57(19) . . ? O6 C15 C16 108.06(18) . . ? O6 C15 H15A 110.1 . . ? C16 C15 H15A 110.1 . . ? O6 C15 H15B 110.1 . . ? C16 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? O7 C16 C15 112.57(18) . . ? O7 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? O7 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? O7 C17 C18 108.38(19) . . ? O7 C17 H17A 110.0 . . ? C18 C17 H17A 110.0 . . ? O7 C17 H17B 110.0 . . ? C18 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? O8 C18 C17 110.00(19) . . ? O8 C18 H18A 109.7 . . ? C17 C18 H18A 109.7 . . ? O8 C18 H18B 109.7 . . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? O8 C19 C20 109.3(2) . . ? O8 C19 H19A 109.8 . . ? C20 C19 H19A 109.8 . . ? O8 C19 H19B 109.8 . . ? C20 C19 H19B 109.8 . . ? H19A C19 H19B 108.3 . . ? O9 C20 C19 107.76(19) . . ? O9 C20 H20A 110.2 . . ? C19 C20 H20A 110.2 . . ? O9 C20 H20B 110.2 . . ? C19 C20 H20B 110.2 . . ? H20A C20 H20B 108.5 . . ? O10 C21 O9 124.5(2) . . ? O10 C21 C1 123.9(2) . . ? O9 C21 C1 111.5(2) . . ? N1 C22 C23 111.22(17) . . ? N1 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? N1 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C28 C23 C24 119.2(2) . . ? C28 C23 C22 119.9(2) . . ? C24 C23 C22 120.9(2) . . ? C25 C24 C23 120.3(2) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? C26 C25 C24 120.0(2) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 120.1(2) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C26 C27 C28 119.6(2) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C23 C28 C27 120.7(2) . . ? C23 C28 H28A 119.6 . . ? C27 C28 H28A 119.6 . . ? N1 C29 C30 111.73(18) . . ? N1 C29 H29A 109.3 . . ? C30 C29 H29A 109.3 . . ? N1 C29 H29B 109.3 . . ? C30 C29 H29B 109.3 . . ? H29A C29 H29B 107.9 . . ? C35 C30 C31 118.9(2) . . ? C35 C30 C29 120.6(2) . . ? C31 C30 C29 120.5(2) . . ? C32 C31 C30 120.4(2) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C33 C32 C31 120.2(2) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C34 119.9(2) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.0 . . ? C33 C34 C35 119.9(2) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C30 C35 C34 120.7(2) . . ? C30 C35 H35 119.6 . . ? C34 C35 H35 119.6 . . ? 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 C3 O2 C2 O1 0.9(3) . . . . ? C3 O2 C2 C1 -179.67(19) . . . . ? C21 C1 C2 O1 -102.1(3) . . . . ? C21 C1 C2 O2 78.5(2) . . . . ? C2 O2 C3 C4 173.0(2) . . . . ? C5 O3 C4 C3 97.7(2) . . . . ? O2 C3 C4 O3 68.4(2) . . . . ? C4 O3 C5 C6 -171.79(19) . . . . ? C7 O4 C6 C5 -168.74(18) . . . . ? O3 C5 C6 O4 -60.7(2) . . . . ? C6 O4 C7 C8 174.08(18) . . . . ? C9 O5 C8 C7 172.14(18) . . . . ? O4 C7 C8 O5 68.4(2) . . . . ? C8 O5 C9 C10 11.2(3) . . . . ? C8 O5 C9 C14 -168.12(19) . . . . ? O5 C9 C10 C11 -175.9(2) . . . . ? C14 C9 C10 C11 3.4(3) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 C13 -2.5(3) . . . . ? C11 C12 C13 C14 1.6(3) . . . . ? C12 C13 C14 O6 -179.0(2) . . . . ? C12 C13 C14 C9 1.8(3) . . . . ? C15 O6 C14 C13 -5.5(3) . . . . ? C15 O6 C14 C9 173.75(18) . . . . ? O5 C9 C14 C13 175.08(19) . . . . ? C10 C9 C14 C13 -4.2(3) . . . . ? O5 C9 C14 O6 -4.2(3) . . . . ? C10 C9 C14 O6 176.50(19) . . . . ? C14 O6 C15 C16 176.04(17) . . . . ? C17 O7 C16 C15 -81.4(2) . . . . ? O6 C15 C16 O7 -71.8(2) . . . . ? C16 O7 C17 C18 174.83(18) . . . . ? C19 O8 C18 C17 -167.20(19) . . . . ? O7 C17 C18 O8 69.0(2) . . . . ? C18 O8 C19 C20 174.33(19) . . . . ? C21 O9 C20 C19 -157.7(2) . . . . ? O8 C19 C20 O9 -63.3(3) . . . . ? C20 O9 C21 O10 6.4(3) . . . . ? C20 O9 C21 C1 -173.2(2) . . . . ? C2 C1 C21 O10 68.1(3) . . . . ? C2 C1 C21 O9 -112.3(2) . . . . ? C29 N1 C22 C23 169.45(19) . . . . ? N1 C22 C23 C28 -128.6(2) . . . . ? N1 C22 C23 C24 49.7(3) . . . . ? C28 C23 C24 C25 1.2(3) . . . . ? C22 C23 C24 C25 -177.0(2) . . . . ? C23 C24 C25 C26 -0.6(3) . . . . ? C24 C25 C26 C27 -0.6(4) . . . . ? C25 C26 C27 C28 1.1(4) . . . . ? C24 C23 C28 C27 -0.7(3) . . . . ? C22 C23 C28 C27 177.6(2) . . . . ? C26 C27 C28 C23 -0.5(4) . . . . ? C22 N1 C29 C30 172.41(19) . . . . ? N1 C29 C30 C35 -109.4(2) . . . . ? N1 C29 C30 C31 70.8(3) . . . . ? C35 C30 C31 C32 0.6(3) . . . . ? C29 C30 C31 C32 -179.6(2) . . . . ? C30 C31 C32 C33 -1.8(4) . . . . ? C31 C32 C33 C34 1.1(4) . . . . ? C32 C33 C34 C35 0.7(4) . . . . ? C31 C30 C35 C34 1.3(3) . . . . ? C29 C30 C35 C34 -178.5(2) . . . . ? C33 C34 C35 C30 -1.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 58.55 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.442 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.044