# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email D.L.Hughes@uea.ac.uk _publ_contact_author_name 'David L. Hughes' loop_ _publ_author_name N.X-L S.Rahman Z.Xi D.L.Hughes C.Redshaw T.Yamato data_carlr6 _database_code_depnum_ccdc_archive 'CCDC 816686' #TrackingRef 'cr6.cif' _audit_creation_method 'SHELXL-97 and CrysAlis RED' _chemical_name_systematic ; ? ; _chemical_name_common Cone-5d _chemical_melting_point ? _chemical_formula_moiety 'C63 H66 F9 N3 O9' _chemical_formula_structural 'calixarene (C6H2OCH2CONHC6H4CF3-2,-tBu-5,-CH2OCH2-3-)3' _chemical_formula_sum 'C63 H66 F9 N3 O9' _chemical_formula_weight 1180.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 16.3465(11) _cell_length_b 23.3116(18) _cell_length_c 17.2917(13) _cell_angle_alpha 90.00 _cell_angle_beta 116.247(7) _cell_angle_gamma 90.00 _cell_volume 5909.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'large, beautiful, colourless' _exptl_crystal_size_max 0.87 _exptl_crystal_size_mid 0.73 _exptl_crystal_size_min 0.51 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2472 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur 3/CCD' _diffrn_measurement_method 'Thin slice \f and \w scans' _diffrn_detector_area_resol_mean 16.0050 _diffrn_reflns_number 42557 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 30.00 _reflns_number_total 16356 _reflns_number_gt 11023 _reflns_threshold_expression I>2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p20 beta ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p20 beta ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p20 beta ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'ORTEP (Johnson, 1971)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997b)' _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^)+(0.0648P)^2^+1.8626P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(6) _refine_ls_number_reflns 16356 _refine_ls_number_parameters 770 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1292 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.48013(11) 0.34144(7) 0.57086(11) 0.0511(4) Uani 1 1 d . . . C1A C 0.55122(15) 0.30263(9) 0.59400(13) 0.0394(5) Uani 1 1 d . . . C2A C 0.60951(15) 0.30303(9) 0.55478(13) 0.0410(5) Uani 1 1 d . . . C3A C 0.67865(16) 0.26204(10) 0.58009(14) 0.0429(5) Uani 1 1 d . . . H3A H 0.7174 0.2621 0.5537 0.052 Uiso 1 1 calc R . . C4A C 0.69225(17) 0.22096(10) 0.64321(14) 0.0463(5) Uani 1 1 d . A . C5A C 0.63549(18) 0.22504(10) 0.68414(15) 0.0470(5) Uani 1 1 d . . . H5A H 0.6442 0.1994 0.7283 0.056 Uiso 1 1 calc R . . C6A C 0.56678(15) 0.26557(10) 0.66185(14) 0.0428(5) Uani 1 1 d . . . C7A C 0.51338(17) 0.27280(11) 0.71364(16) 0.0505(6) Uani 1 1 d . . . H7A1 H 0.4491 0.2772 0.6748 0.061 Uiso 1 1 calc R . . H7A2 H 0.5204 0.2388 0.7483 0.061 Uiso 1 1 calc R . . O8A O 0.54469(11) 0.32209(7) 0.76871(10) 0.0488(4) Uani 1 1 d . . . C9A C 0.63062(16) 0.31335(10) 0.84217(15) 0.0471(5) Uani 1 1 d . . . H9A1 H 0.6593 0.2792 0.8333 0.057 Uiso 1 1 calc R . . H9A2 H 0.6205 0.3072 0.8927 0.057 Uiso 1 1 calc R . . C11A C 0.40719(19) 0.33450(13) 0.48623(19) 0.0647(7) Uani 1 1 d . . . H11A H 0.4252 0.3073 0.4542 0.078 Uiso 1 1 calc R . . H11B H 0.3948 0.3709 0.4561 0.078 Uiso 1 1 calc R . . C12A C 0.3220(2) 0.31347(14) 0.4901(2) 0.0721(9) Uani 1 1 d . . . O12A O 0.3052(2) 0.26276(13) 0.4850(4) 0.169(2) Uani 1 1 d . . . N13A N 0.26865(17) 0.35308(11) 0.50021(16) 0.0649(6) Uani 1 1 d . . . H13A H 0.2890 0.3876 0.5059 0.078 Uiso 1 1 calc R . . C14A C 0.18385(19) 0.34719(12) 0.50301(16) 0.0566(6) Uani 1 1 d . . . C15A C 0.1459(2) 0.29492(14) 0.5068(2) 0.0716(8) Uani 1 1 d . . . H15A H 0.1767 0.2610 0.5087 0.086 Uiso 1 1 calc R . . C16A C 0.0618(2) 0.29314(16) 0.5078(2) 0.0814(9) Uani 1 1 d . . . H16A H 0.0356 0.2579 0.5085 0.098 Uiso 1 1 calc R . . C17A C 0.0164(2) 0.34274(16) 0.50786(19) 0.0715(8) Uani 1 1 d . . . C18A C 0.0549(2) 0.39476(15) 0.5053(2) 0.0726(8) Uani 1 1 d . . . H18A H 0.0247 0.4285 0.5055 0.087 Uiso 1 1 calc R . . C19A C 0.1379(2) 0.39732(14) 0.50263(19) 0.0662(7) Uani 1 1 d . . . H19A H 0.1631 0.4327 0.5006 0.079 Uiso 1 1 calc R . . C41A C 0.7666(2) 0.17522(12) 0.66994(17) 0.0599(7) Uani 1 1 d . . . C42A C 0.8178(8) 0.1772(5) 0.6165(6) 0.215(8) Uani 0.783(9) 1 d P A 1 H42A H 0.7760 0.1723 0.5568 0.322 Uiso 0.783(9) 1 calc PR A 1 H42B H 0.8623 0.1470 0.6341 0.322 Uiso 0.783(9) 1 calc PR A 1 H42C H 0.8479 0.2136 0.6242 0.322 Uiso 0.783(9) 1 calc PR A 1 C43A C 0.8307(5) 0.1799(4) 0.7628(4) 0.159(5) Uani 0.783(9) 1 d P A 1 H43A H 0.7970 0.1793 0.7963 0.239 Uiso 0.783(9) 1 calc PR A 1 H43B H 0.8640 0.2152 0.7730 0.239 Uiso 0.783(9) 1 calc PR A 1 H43C H 0.8725 0.1482 0.7793 0.239 Uiso 0.783(9) 1 calc PR A 1 C44A C 0.7224(5) 0.1168(3) 0.6530(9) 0.199(7) Uani 0.783(9) 1 d P A 1 H44A H 0.6895 0.1121 0.6869 0.299 Uiso 0.783(9) 1 calc PR A 1 H44B H 0.7685 0.0877 0.6684 0.299 Uiso 0.783(9) 1 calc PR A 1 H44C H 0.6809 0.1134 0.5929 0.299 Uiso 0.783(9) 1 calc PR A 1 C46A C 0.8562(13) 0.2077(8) 0.7144(14) 0.089(6) Uiso 0.217(9) 1 d P A 2 H46A H 0.8536 0.2328 0.7573 0.133 Uiso 0.217(9) 1 calc PR A 2 H46B H 0.8662 0.2298 0.6726 0.133 Uiso 0.217(9) 1 calc PR A 2 H46C H 0.9053 0.1809 0.7415 0.133 Uiso 0.217(9) 1 calc PR A 2 C47A C 0.7575(12) 0.1327(7) 0.7328(11) 0.073(5) Uiso 0.217(9) 1 d P A 2 H47A H 0.7720 0.1516 0.7867 0.109 Uiso 0.217(9) 1 calc PR A 2 H47B H 0.7988 0.1013 0.7422 0.109 Uiso 0.217(9) 1 calc PR A 2 H47C H 0.6961 0.1186 0.7092 0.109 Uiso 0.217(9) 1 calc PR A 2 C48A C 0.7477(14) 0.1390(9) 0.5972(11) 0.076(5) Uiso 0.217(9) 1 d P A 2 H48A H 0.7939 0.1099 0.6127 0.115 Uiso 0.217(9) 1 calc PR A 2 H48B H 0.7473 0.1615 0.5506 0.115 Uiso 0.217(9) 1 calc PR A 2 H48C H 0.6892 0.1212 0.5795 0.115 Uiso 0.217(9) 1 calc PR A 2 C71A C -0.0751(3) 0.3420(2) 0.5077(3) 0.1023(13) Uani 1 1 d . . . F72A F -0.0954(2) 0.29319(17) 0.5331(2) 0.1512(12) Uani 1 1 d . . . F73A F -0.0848(3) 0.3799(2) 0.5563(4) 0.206(2) Uani 1 1 d . . . F74A F -0.1414(2) 0.3496(2) 0.4304(3) 0.194(2) Uani 1 1 d . . . O1B O 0.58594(10) 0.42487(7) 0.87623(9) 0.0422(3) Uani 1 1 d . . . C1B C 0.66926(14) 0.41808(9) 0.87358(12) 0.0375(4) Uani 1 1 d . . . C2B C 0.69372(15) 0.36378(9) 0.85792(13) 0.0391(4) Uani 1 1 d . . . C3B C 0.77840(16) 0.35667(10) 0.85904(14) 0.0441(5) Uani 1 1 d . . . H3B H 0.7950 0.3204 0.8485 0.053 Uiso 1 1 calc R . . C4B C 0.83949(15) 0.40194(10) 0.87546(14) 0.0430(5) Uani 1 1 d . . . C5B C 0.80947(15) 0.45586(10) 0.88431(13) 0.0406(5) Uani 1 1 d . . . H5B H 0.8475 0.4871 0.8913 0.049 Uiso 1 1 calc R . . C6B C 0.72487(15) 0.46547(9) 0.88317(12) 0.0383(4) Uani 1 1 d . . . C7B C 0.69293(15) 0.52496(10) 0.89144(14) 0.0439(5) Uani 1 1 d . . . H7B1 H 0.6772 0.5255 0.9393 0.053 Uiso 1 1 calc R . . H7B2 H 0.7425 0.5519 0.9043 0.053 Uiso 1 1 calc R . . O8B O 0.61607(11) 0.54309(7) 0.81528(10) 0.0461(4) Uani 1 1 d . . . C9B C 0.6364(2) 0.57779(10) 0.75735(17) 0.0540(6) Uani 1 1 d . . . H9B1 H 0.6693 0.6115 0.7886 0.065 Uiso 1 1 calc R . . H9B2 H 0.5792 0.5909 0.7115 0.065 Uiso 1 1 calc R . . C11B C 0.59000(19) 0.41840(13) 0.96001(15) 0.0557(6) Uani 1 1 d . . . H11C H 0.5940 0.4559 0.9856 0.067 Uiso 1 1 calc R . . H11D H 0.6444 0.3971 0.9965 0.067 Uiso 1 1 calc R . . C12B C 0.50682(17) 0.38728(11) 0.95601(15) 0.0505(6) Uani 1 1 d . . . O12B O 0.49170(16) 0.38794(11) 1.01882(13) 0.0777(6) Uani 1 1 d . . . N13B N 0.45630(14) 0.36067(10) 0.88171(12) 0.0515(5) Uani 1 1 d . . . H13B H 0.4775 0.3611 0.8442 0.062 Uiso 1 1 calc R . . C14B C 0.37206(17) 0.33175(11) 0.85673(15) 0.0486(5) Uani 1 1 d . . . C15B C 0.3261(2) 0.32929(16) 0.9064(2) 0.0753(9) Uani 1 1 d . . . H15B H 0.3511 0.3458 0.9609 0.090 Uiso 1 1 calc R . . C16B C 0.2423(2) 0.30212(17) 0.8749(2) 0.0778(10) Uani 1 1 d . . . H16B H 0.2114 0.3008 0.9089 0.093 Uiso 1 1 calc R . . C17B C 0.20413(19) 0.27741(12) 0.79578(19) 0.0589(6) Uani 1 1 d . . . C18B C 0.2500(2) 0.27918(19) 0.7464(2) 0.0870(11) Uani 1 1 d . . . H18B H 0.2250 0.2621 0.6922 0.104 Uiso 1 1 calc R . . C19B C 0.3337(2) 0.30633(18) 0.7769(2) 0.0808(10) Uani 1 1 d . . . H19B H 0.3645 0.3074 0.7428 0.097 Uiso 1 1 calc R . . C41B C 0.93471(17) 0.39131(12) 0.88109(16) 0.0517(6) Uani 1 1 d . . . C42B C 0.9981(2) 0.44226(16) 0.9197(2) 0.0775(9) Uani 1 1 d . . . H42D H 1.0567 0.4339 0.9222 0.116 Uiso 1 1 calc R . . H42E H 1.0047 0.4495 0.9769 0.116 Uiso 1 1 calc R . . H42F H 0.9728 0.4755 0.8844 0.116 Uiso 1 1 calc R . . C43B C 0.9260(2) 0.37975(19) 0.7910(2) 0.0821(10) Uani 1 1 d . . . H43D H 0.9854 0.3729 0.7944 0.123 Uiso 1 1 calc R . . H43E H 0.8990 0.4124 0.7549 0.123 Uiso 1 1 calc R . . H43F H 0.8882 0.3467 0.7671 0.123 Uiso 1 1 calc R . . C44B C 0.9779(2) 0.33892(17) 0.9378(3) 0.0848(10) Uani 1 1 d . . . H44D H 1.0373 0.3323 0.9410 0.127 Uiso 1 1 calc R . . H44E H 0.9401 0.3059 0.9133 0.127 Uiso 1 1 calc R . . H44F H 0.9833 0.3457 0.9946 0.127 Uiso 1 1 calc R . . C71B C 0.1118(2) 0.25082(14) 0.7619(2) 0.0736(8) Uani 1 1 d . . . F72B F 0.09453(16) 0.21443(10) 0.69750(16) 0.1061(7) Uani 1 1 d . . . F73B F 0.0998(2) 0.22106(18) 0.81953(18) 0.1572(15) Uani 1 1 d . . . F74B F 0.04652(16) 0.28883(12) 0.7277(3) 0.1400(12) Uani 1 1 d . . . O1C O 0.59399(10) 0.46722(6) 0.67725(9) 0.0421(3) Uani 1 1 d . . . C1C C 0.66831(15) 0.49647(9) 0.67746(13) 0.0393(5) Uani 1 1 d . . . C2C C 0.69089(17) 0.55020(10) 0.71661(14) 0.0447(5) Uani 1 1 d . . . C3C C 0.76520(18) 0.57853(10) 0.71596(15) 0.0494(6) Uani 1 1 d . . . H3C H 0.7815 0.6141 0.7427 0.059 Uiso 1 1 calc R . . C4C C 0.81645(16) 0.55572(11) 0.67675(14) 0.0463(5) Uani 1 1 d . . . C5C C 0.79237(16) 0.50185(10) 0.63971(14) 0.0433(5) Uani 1 1 d . . . H5C H 0.8262 0.4857 0.6139 0.052 Uiso 1 1 calc R . . C6C C 0.71937(15) 0.47101(9) 0.63976(13) 0.0387(4) Uani 1 1 d . . . C7C C 0.70187(16) 0.41023(10) 0.60776(14) 0.0434(5) Uani 1 1 d . . . H7C1 H 0.7527 0.3967 0.5981 0.052 Uiso 1 1 calc R . . H7C2 H 0.6972 0.3859 0.6511 0.052 Uiso 1 1 calc R . . O8C O 0.61975(11) 0.40630(7) 0.52945(9) 0.0432(3) Uani 1 1 d . . . C9C C 0.60670(19) 0.34985(10) 0.49281(14) 0.0479(5) Uani 1 1 d . . . H9C1 H 0.6537 0.3424 0.4743 0.057 Uiso 1 1 calc R . . H9C2 H 0.5482 0.3485 0.4422 0.057 Uiso 1 1 calc R . . C11C C 0.51094(16) 0.47701(11) 0.60284(14) 0.0453(5) Uani 1 1 d . . . H11E H 0.5054 0.4499 0.5582 0.054 Uiso 1 1 calc R . . H11F H 0.5112 0.5154 0.5813 0.054 Uiso 1 1 calc R . . C12C C 0.43083(16) 0.47061(10) 0.62257(15) 0.0440(5) Uani 1 1 d . . . O12C O 0.35566(12) 0.45956(8) 0.56361(11) 0.0558(4) Uani 1 1 d . . . N13C N 0.44700(13) 0.48072(10) 0.70460(12) 0.0514(5) Uani 1 1 d . . . H13C H 0.5024 0.4888 0.7399 0.062 Uiso 1 1 calc R . . C14C C 0.38385(16) 0.47961(11) 0.73941(15) 0.0486(5) Uani 1 1 d . . . C15C C 0.3006(2) 0.45235(16) 0.69860(19) 0.0742(9) Uani 1 1 d . . . H15C H 0.2846 0.4341 0.6461 0.089 Uiso 1 1 calc R . . C16C C 0.2410(2) 0.45206(18) 0.7353(2) 0.0791(10) Uani 1 1 d . . . H16C H 0.1847 0.4340 0.7071 0.095 Uiso 1 1 calc R . . C17C C 0.26414(19) 0.47819(14) 0.81293(18) 0.0607(7) Uani 1 1 d . . . C18C C 0.34819(19) 0.50315(13) 0.85547(17) 0.0589(6) Uani 1 1 d . . . H18C H 0.3651 0.5194 0.9095 0.071 Uiso 1 1 calc R . . C19C C 0.40777(17) 0.50450(12) 0.81913(16) 0.0521(6) Uani 1 1 d . . . H19C H 0.4643 0.5222 0.8482 0.062 Uiso 1 1 calc R . . C41C C 0.89629(19) 0.59000(12) 0.67582(16) 0.0572(7) Uani 1 1 d . . . C42C C 0.9505(3) 0.55467(19) 0.6393(2) 0.0887(11) Uani 1 1 d . . . H42G H 0.9107 0.5429 0.5815 0.133 Uiso 1 1 calc R . . H42H H 0.9755 0.5214 0.6746 0.133 Uiso 1 1 calc R . . H42I H 0.9991 0.5776 0.6389 0.133 Uiso 1 1 calc R . . C43C C 0.8587(3) 0.64312(16) 0.6181(2) 0.0870(11) Uani 1 1 d . . . H43G H 0.8242 0.6660 0.6393 0.131 Uiso 1 1 calc R . . H43H H 0.8200 0.6312 0.5601 0.131 Uiso 1 1 calc R . . H43I H 0.9084 0.6654 0.6188 0.131 Uiso 1 1 calc R . . C44C C 0.9613(2) 0.60851(17) 0.76770(19) 0.0791(10) Uani 1 1 d . . . H44G H 0.9285 0.6310 0.7913 0.119 Uiso 1 1 calc R . . H44H H 1.0099 0.6310 0.7666 0.119 Uiso 1 1 calc R . . H44I H 0.9862 0.5751 0.8028 0.119 Uiso 1 1 calc R . . C71C C 0.1984(2) 0.4777(2) 0.8513(2) 0.0851(11) Uani 1 1 d . . . F72C F 0.12181(17) 0.45143(18) 0.80384(18) 0.1551(15) Uani 1 1 d . . . F73C F 0.1759(2) 0.53027(15) 0.8629(2) 0.1456(12) Uani 1 1 d . . . F74C F 0.23101(18) 0.45557(14) 0.92852(16) 0.1168(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0410(8) 0.0529(10) 0.0526(9) -0.0158(7) 0.0145(7) 0.0025(7) C1A 0.0406(11) 0.0365(11) 0.0395(10) -0.0122(8) 0.0162(9) -0.0043(9) C2A 0.0475(12) 0.0397(11) 0.0340(10) -0.0100(8) 0.0165(9) -0.0047(9) C3A 0.0466(12) 0.0465(12) 0.0403(10) -0.0084(9) 0.0235(9) -0.0026(10) C4A 0.0507(13) 0.0425(12) 0.0436(11) -0.0090(9) 0.0191(10) -0.0011(10) C5A 0.0601(14) 0.0398(12) 0.0451(12) -0.0058(9) 0.0270(11) -0.0054(10) C6A 0.0449(12) 0.0434(12) 0.0442(11) -0.0124(9) 0.0235(10) -0.0120(9) C7A 0.0474(13) 0.0571(14) 0.0555(13) -0.0161(11) 0.0306(11) -0.0174(11) O8A 0.0442(9) 0.0529(9) 0.0487(9) -0.0146(7) 0.0201(7) -0.0054(7) C9A 0.0494(13) 0.0464(13) 0.0461(12) -0.0023(9) 0.0216(10) -0.0043(10) C11A 0.0499(14) 0.0677(17) 0.0596(15) -0.0069(13) 0.0087(12) 0.0063(13) C12A 0.0489(15) 0.0586(17) 0.089(2) -0.0137(15) 0.0122(15) 0.0005(13) O12A 0.094(2) 0.0715(18) 0.349(7) -0.048(3) 0.106(3) -0.0113(16) N13A 0.0678(15) 0.0572(14) 0.0712(15) -0.0153(11) 0.0321(12) -0.0081(11) C14A 0.0565(16) 0.0637(16) 0.0422(12) -0.0121(11) 0.0152(11) -0.0052(12) C15A 0.072(2) 0.0645(19) 0.0732(18) -0.0149(15) 0.0272(16) -0.0056(15) C16A 0.075(2) 0.073(2) 0.085(2) -0.0078(17) 0.0256(18) -0.0168(18) C17A 0.0566(17) 0.089(2) 0.0592(16) 0.0069(15) 0.0166(13) -0.0021(16) C18A 0.072(2) 0.075(2) 0.0683(18) 0.0097(15) 0.0290(15) 0.0122(16) C19A 0.0728(19) 0.0585(17) 0.0651(17) 0.0022(13) 0.0286(15) 0.0050(14) C41A 0.0665(16) 0.0574(16) 0.0520(14) -0.0018(12) 0.0226(12) 0.0155(13) C42A 0.268(12) 0.273(13) 0.213(9) 0.159(9) 0.205(10) 0.229(12) C43A 0.123(6) 0.240(10) 0.066(3) -0.020(5) -0.002(3) 0.106(7) C44A 0.096(5) 0.064(4) 0.343(17) -0.017(6) 0.011(7) 0.025(3) C71A 0.073(3) 0.122(4) 0.113(3) 0.016(3) 0.043(3) 0.000(2) F72A 0.1001(19) 0.172(3) 0.193(3) 0.046(2) 0.076(2) -0.0082(19) F73A 0.162(3) 0.230(4) 0.309(6) -0.098(4) 0.180(4) -0.043(3) F74A 0.0735(16) 0.332(6) 0.157(3) 0.100(3) 0.0318(19) 0.037(2) O1B 0.0391(8) 0.0542(9) 0.0390(7) -0.0070(7) 0.0224(6) -0.0051(7) C1B 0.0374(11) 0.0472(12) 0.0286(9) -0.0034(8) 0.0153(8) -0.0016(9) C2B 0.0425(11) 0.0430(12) 0.0322(9) -0.0018(8) 0.0168(8) -0.0031(9) C3B 0.0520(13) 0.0424(12) 0.0414(11) 0.0021(9) 0.0237(10) 0.0075(10) C4B 0.0416(11) 0.0515(13) 0.0383(10) 0.0039(9) 0.0200(9) 0.0026(10) C5B 0.0395(11) 0.0440(12) 0.0403(10) -0.0011(9) 0.0195(9) -0.0052(9) C6B 0.0410(11) 0.0414(12) 0.0328(9) -0.0026(8) 0.0165(8) -0.0008(9) C7B 0.0418(12) 0.0459(12) 0.0439(11) -0.0085(9) 0.0190(10) -0.0029(9) O8B 0.0469(9) 0.0481(9) 0.0488(8) 0.0008(7) 0.0261(7) 0.0038(7) C9B 0.0693(17) 0.0410(13) 0.0599(14) 0.0033(11) 0.0361(13) 0.0081(11) C11B 0.0553(15) 0.0756(18) 0.0438(12) -0.0155(11) 0.0287(11) -0.0152(13) C12B 0.0547(14) 0.0569(14) 0.0465(13) -0.0040(11) 0.0284(11) -0.0065(11) O12B 0.0875(15) 0.1081(17) 0.0552(11) -0.0235(11) 0.0477(11) -0.0366(13) N13B 0.0512(11) 0.0679(14) 0.0458(11) -0.0083(9) 0.0310(9) -0.0123(10) C14B 0.0493(13) 0.0539(14) 0.0460(12) -0.0036(10) 0.0243(10) -0.0043(11) C15B 0.081(2) 0.099(2) 0.0622(17) -0.0187(16) 0.0465(16) -0.0367(18) C16B 0.072(2) 0.108(3) 0.0689(18) -0.0095(17) 0.0451(17) -0.0314(19) C17B 0.0538(15) 0.0545(15) 0.0686(17) 0.0022(13) 0.0274(13) -0.0041(12) C18B 0.0630(19) 0.127(3) 0.075(2) -0.041(2) 0.0337(17) -0.0260(19) C19B 0.0592(17) 0.130(3) 0.0636(17) -0.0355(18) 0.0365(14) -0.0200(19) C41B 0.0436(12) 0.0601(15) 0.0551(13) 0.0076(11) 0.0252(11) 0.0063(11) C42B 0.0509(16) 0.086(2) 0.106(3) -0.0088(19) 0.0451(17) -0.0059(15) C43B 0.0674(19) 0.119(3) 0.0735(19) -0.0004(19) 0.0436(16) 0.0216(19) C44B 0.0570(17) 0.090(2) 0.104(3) 0.039(2) 0.0324(18) 0.0243(16) C71B 0.0619(18) 0.0678(19) 0.093(2) -0.0052(17) 0.0359(18) -0.0091(16) F72B 0.0915(15) 0.0928(15) 0.1193(17) -0.0296(13) 0.0331(13) -0.0330(12) F73B 0.125(2) 0.239(4) 0.1077(18) 0.007(2) 0.0516(16) -0.102(2) F74B 0.0609(12) 0.0955(16) 0.228(3) -0.0243(19) 0.0319(16) 0.0055(12) O1C 0.0400(8) 0.0453(8) 0.0436(8) 0.0081(6) 0.0209(7) -0.0021(7) C1C 0.0421(11) 0.0398(11) 0.0362(10) 0.0057(8) 0.0174(9) -0.0031(9) C2C 0.0559(13) 0.0392(12) 0.0427(11) 0.0061(9) 0.0251(10) 0.0027(10) C3C 0.0638(15) 0.0379(12) 0.0468(12) -0.0015(9) 0.0247(11) -0.0110(10) C4C 0.0480(13) 0.0509(13) 0.0396(11) 0.0039(10) 0.0191(10) -0.0099(10) C5C 0.0452(12) 0.0496(13) 0.0376(10) 0.0036(9) 0.0205(9) -0.0039(10) C6C 0.0405(11) 0.0410(11) 0.0335(9) 0.0019(8) 0.0152(9) -0.0019(9) C7C 0.0463(12) 0.0428(12) 0.0409(11) 0.0017(9) 0.0192(10) -0.0017(9) O8C 0.0531(9) 0.0416(8) 0.0344(7) -0.0008(6) 0.0189(7) 0.0005(7) C9C 0.0611(14) 0.0490(13) 0.0353(10) -0.0065(9) 0.0229(10) -0.0025(11) C11C 0.0463(13) 0.0505(13) 0.0406(11) 0.0026(9) 0.0206(10) 0.0020(10) C12C 0.0461(13) 0.0416(12) 0.0463(12) 0.0032(9) 0.0223(10) 0.0051(10) O12C 0.0461(10) 0.0685(11) 0.0493(9) -0.0017(8) 0.0178(8) -0.0042(8) N13C 0.0382(10) 0.0756(14) 0.0431(10) -0.0001(9) 0.0205(8) -0.0023(9) C14C 0.0449(13) 0.0563(14) 0.0479(12) 0.0025(10) 0.0237(10) 0.0038(10) C15C 0.0657(18) 0.110(3) 0.0567(15) -0.0242(16) 0.0355(14) -0.0255(17) C16C 0.0554(17) 0.122(3) 0.0678(18) -0.0244(18) 0.0342(15) -0.0334(18) C17C 0.0513(15) 0.0770(19) 0.0622(15) -0.0015(13) 0.0328(13) 0.0034(13) C18C 0.0544(15) 0.0757(18) 0.0491(13) -0.0083(12) 0.0253(12) 0.0042(13) C19C 0.0414(12) 0.0623(15) 0.0519(13) -0.0038(11) 0.0202(10) 0.0034(11) C41C 0.0570(15) 0.0666(17) 0.0468(13) 0.0002(11) 0.0218(11) -0.0262(13) C42C 0.079(2) 0.115(3) 0.090(2) -0.022(2) 0.054(2) -0.043(2) C43C 0.087(2) 0.091(2) 0.0693(19) 0.0232(17) 0.0225(17) -0.0379(19) C44C 0.074(2) 0.096(2) 0.0563(16) -0.0056(15) 0.0192(15) -0.0379(18) C71C 0.064(2) 0.132(3) 0.077(2) -0.019(2) 0.0467(18) -0.005(2) F72C 0.0849(16) 0.288(4) 0.127(2) -0.082(2) 0.0781(16) -0.080(2) F73C 0.147(3) 0.165(3) 0.185(3) -0.007(2) 0.129(2) 0.042(2) F74C 0.1136(18) 0.176(3) 0.0918(15) 0.0060(15) 0.0738(14) -0.0103(17) _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 O1A C1A 1.385(3) . ? O1A C11A 1.430(3) . ? C1A C6A 1.387(3) . ? C1A C2A 1.393(3) . ? C2A C3A 1.394(3) . ? C2A C9C 1.516(3) . ? C3A C4A 1.394(3) . ? C4A C5A 1.397(3) . ? C4A C41A 1.527(4) . ? C5A C6A 1.386(3) . ? C6A C7A 1.511(3) . ? C7A O8A 1.434(3) . ? O8A C9A 1.432(3) . ? C9A C2B 1.507(3) . ? C11A C12A 1.506(5) . ? C12A O12A 1.208(4) . ? C12A N13A 1.333(4) . ? N13A C14A 1.415(4) . ? C14A C15A 1.382(4) . ? C14A C19A 1.388(4) . ? C15A C16A 1.383(5) . ? C16A C17A 1.374(5) . ? C17A C18A 1.376(5) . ? C17A C71A 1.495(6) . ? C18A C19A 1.379(5) . ? C41A C48A 1.431(18) . ? C41A C43A 1.484(6) . ? C41A C42A 1.497(7) . ? C41A C44A 1.508(8) . ? C41A C46A 1.520(19) . ? C41A C47A 1.526(16) . ? C71A F73A 1.277(6) . ? C71A F74A 1.309(5) . ? C71A F72A 1.315(6) . ? O1B C1B 1.392(2) . ? O1B C11B 1.429(3) . ? C1B C2B 1.390(3) . ? C1B C6B 1.393(3) . ? C2B C3B 1.386(3) . ? C3B C4B 1.393(3) . ? C4B C5B 1.382(3) . ? C4B C41B 1.536(3) . ? C5B C6B 1.392(3) . ? C6B C7B 1.511(3) . ? C7B O8B 1.424(3) . ? O8B C9B 1.436(3) . ? C9B C2C 1.503(3) . ? C11B C12B 1.515(4) . ? C12B O12B 1.216(3) . ? C12B N13B 1.334(3) . ? N13B C14B 1.418(3) . ? C14B C15B 1.368(4) . ? C14B C19B 1.373(4) . ? C15B C16B 1.384(4) . ? C16B C17B 1.356(4) . ? C17B C18B 1.363(4) . ? C17B C71B 1.491(4) . ? C18B C19B 1.383(5) . ? C41B C42B 1.523(4) . ? C41B C43B 1.524(4) . ? C41B C44B 1.529(4) . ? C71B F73B 1.299(4) . ? C71B F74B 1.309(4) . ? C71B F72B 1.327(4) . ? O1C C1C 1.392(3) . ? O1C C11C 1.416(3) . ? C1C C2C 1.394(3) . ? C1C C6C 1.398(3) . ? C2C C3C 1.387(4) . ? C3C C4C 1.395(4) . ? C4C C5C 1.385(4) . ? C4C C41C 1.537(3) . ? C5C C6C 1.394(3) . ? C6C C7C 1.502(3) . ? C7C O8C 1.427(3) . ? O8C C9C 1.435(3) . ? C11C C12C 1.500(3) . ? C12C O12C 1.228(3) . ? C12C N13C 1.344(3) . ? N13C C14C 1.407(3) . ? C14C C15C 1.380(4) . ? C14C C19C 1.383(3) . ? C15C C16C 1.378(4) . ? C16C C17C 1.366(4) . ? C17C C18C 1.369(4) . ? C17C C71C 1.493(4) . ? C18C C19C 1.373(4) . ? C41C C44C 1.532(4) . ? C41C C42C 1.535(5) . ? C41C C43C 1.538(4) . ? C71C F74C 1.304(5) . ? C71C F72C 1.306(4) . ? C71C F73C 1.321(5) . ? 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 C1A O1A C11A 115.79(18) . . ? O1A C1A C6A 117.89(19) . . ? O1A C1A C2A 121.5(2) . . ? C6A C1A C2A 120.5(2) . . ? C1A C2A C3A 118.5(2) . . ? C1A C2A C9C 122.4(2) . . ? C3A C2A C9C 118.8(2) . . ? C4A C3A C2A 122.9(2) . . ? C3A C4A C5A 116.0(2) . . ? C3A C4A C41A 123.2(2) . . ? C5A C4A C41A 120.8(2) . . ? C6A C5A C4A 122.9(2) . . ? C5A C6A C1A 118.9(2) . . ? C5A C6A C7A 121.4(2) . . ? C1A C6A C7A 119.6(2) . . ? O8A C7A C6A 110.65(18) . . ? C9A O8A C7A 113.39(19) . . ? O8A C9A C2B 111.96(19) . . ? O1A C11A C12A 111.1(3) . . ? O12A C12A N13A 123.1(3) . . ? O12A C12A C11A 120.0(3) . . ? N13A C12A C11A 116.8(3) . . ? C12A N13A C14A 130.1(3) . . ? C15A C14A C19A 119.3(3) . . ? C15A C14A N13A 123.7(3) . . ? C19A C14A N13A 117.0(3) . . ? C14A C15A C16A 119.8(3) . . ? C17A C16A C15A 121.0(3) . . ? C16A C17A C18A 119.2(3) . . ? C16A C17A C71A 122.0(4) . . ? C18A C17A C71A 118.8(4) . . ? C17A C18A C19A 120.7(3) . . ? C18A C19A C14A 120.1(3) . . ? C48A C41A C43A 140.3(8) . . ? C48A C41A C42A 55.8(9) . . ? C43A C41A C42A 110.3(6) . . ? C48A C41A C44A 53.0(8) . . ? C43A C41A C44A 109.0(7) . . ? C42A C41A C44A 105.0(7) . . ? C48A C41A C46A 121.6(12) . . ? C43A C41A C46A 49.8(8) . . ? C42A C41A C46A 67.7(10) . . ? C44A C41A C46A 145.0(8) . . ? C48A C41A C47A 101.1(11) . . ? C43A C41A C47A 61.4(8) . . ? C42A C41A C47A 135.8(7) . . ? C44A C41A C47A 50.4(8) . . ? C46A C41A C47A 109.7(11) . . ? C48A C41A C4A 108.2(8) . . ? C43A C41A C4A 111.3(3) . . ? C42A C41A C4A 112.3(3) . . ? C44A C41A C4A 108.8(3) . . ? C46A C41A C4A 105.4(8) . . ? C47A C41A C4A 110.7(7) . . ? F73A C71A F74A 106.9(5) . . ? F73A C71A F72A 104.8(4) . . ? F74A C71A F72A 104.0(4) . . ? F73A C71A C17A 114.0(4) . . ? F74A C71A C17A 112.1(4) . . ? F72A C71A C17A 114.2(4) . . ? C1B O1B C11B 114.46(17) . . ? C2B C1B O1B 118.69(19) . . ? C2B C1B C6B 121.10(19) . . ? O1B C1B C6B 120.15(19) . . ? C3B C2B C1B 118.6(2) . . ? C3B C2B C9A 120.6(2) . . ? C1B C2B C9A 120.8(2) . . ? C2B C3B C4B 122.3(2) . . ? C5B C4B C3B 117.0(2) . . ? C5B C4B C41B 122.6(2) . . ? C3B C4B C41B 120.4(2) . . ? C4B C5B C6B 122.9(2) . . ? C5B C6B C1B 117.8(2) . . ? C5B C6B C7B 121.9(2) . . ? C1B C6B C7B 120.30(19) . . ? O8B C7B C6B 112.68(17) . . ? C7B O8B C9B 115.49(19) . . ? O8B C9B C2C 117.00(19) . . ? O1B C11B C12B 111.47(19) . . ? O12B C12B N13B 125.6(2) . . ? O12B C12B C11B 119.1(2) . . ? N13B C12B C11B 115.30(19) . . ? C12B N13B C14B 128.2(2) . . ? C15B C14B C19B 118.6(3) . . ? C15B C14B N13B 123.8(2) . . ? C19B C14B N13B 117.5(2) . . ? C14B C15B C16B 119.7(3) . . ? C17B C16B C15B 121.7(3) . . ? C16B C17B C18B 118.9(3) . . ? C16B C17B C71B 120.5(3) . . ? C18B C17B C71B 120.5(3) . . ? C17B C18B C19B 120.0(3) . . ? C14B C19B C18B 121.0(3) . . ? C42B C41B C43B 108.9(3) . . ? C42B C41B C44B 108.1(3) . . ? C43B C41B C44B 108.8(3) . . ? C42B C41B C4B 112.1(2) . . ? C43B C41B C4B 109.3(2) . . ? C44B C41B C4B 109.7(2) . . ? F73B C71B F74B 109.8(4) . . ? F73B C71B F72B 104.7(3) . . ? F74B C71B F72B 103.0(3) . . ? F73B C71B C17B 113.0(3) . . ? F74B C71B C17B 112.2(3) . . ? F72B C71B C17B 113.5(3) . . ? C1C O1C C11C 114.11(16) . . ? O1C C1C C2C 119.02(19) . . ? O1C C1C C6C 119.41(19) . . ? C2C C1C C6C 121.6(2) . . ? C3C C2C C1C 118.0(2) . . ? C3C C2C C9B 120.2(2) . . ? C1C C2C C9B 121.9(2) . . ? C2C C3C C4C 122.6(2) . . ? C5C C4C C3C 117.5(2) . . ? C5C C4C C41C 122.4(2) . . ? C3C C4C C41C 120.1(2) . . ? C4C C5C C6C 122.4(2) . . ? C5C C6C C1C 118.0(2) . . ? C5C C6C C7C 120.7(2) . . ? C1C C6C C7C 121.1(2) . . ? O8C C7C C6C 110.87(18) . . ? C7C O8C C9C 111.82(17) . . ? O8C C9C C2A 113.33(17) . . ? O1C C11C C12C 111.11(17) . . ? O12C C12C N13C 124.8(2) . . ? O12C C12C C11C 119.1(2) . . ? N13C C12C C11C 116.0(2) . . ? C12C N13C C14C 127.6(2) . . ? C15C C14C C19C 118.9(2) . . ? C15C C14C N13C 122.3(2) . . ? C19C C14C N13C 118.8(2) . . ? C16C C15C C14C 120.3(3) . . ? C17C C16C C15C 120.4(3) . . ? C16C C17C C18C 119.6(2) . . ? C16C C17C C71C 119.5(3) . . ? C18C C17C C71C 120.9(3) . . ? C17C C18C C19C 120.7(2) . . ? C18C C19C C14C 120.1(2) . . ? C44C C41C C42C 108.4(3) . . ? C44C C41C C4C 109.8(2) . . ? C42C C41C C4C 111.9(2) . . ? C44C C41C C43C 109.9(3) . . ? C42C C41C C43C 107.6(3) . . ? C4C C41C C43C 109.1(2) . . ? F74C C71C F72C 107.7(4) . . ? F74C C71C F73C 103.1(3) . . ? F72C C71C F73C 106.0(4) . . ? F74C C71C C17C 114.2(3) . . ? F72C C71C C17C 113.7(3) . . ? F73C C71C C17C 111.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11A O1A C1A C6A -116.1(2) . . . . ? C11A O1A C1A C2A 68.3(3) . . . . ? O1A C1A C2A C3A -178.83(18) . . . . ? C6A C1A C2A C3A 5.6(3) . . . . ? O1A C1A C2A C9C 7.7(3) . . . . ? C6A C1A C2A C9C -167.91(19) . . . . ? C1A C2A C3A C4A -0.4(3) . . . . ? C9C C2A C3A C4A 173.4(2) . . . . ? C2A C3A C4A C5A -3.6(3) . . . . ? C2A C3A C4A C41A 178.7(2) . . . . ? C3A C4A C5A C6A 2.7(3) . . . . ? C41A C4A C5A C6A -179.6(2) . . . . ? C4A C5A C6A C1A 2.3(3) . . . . ? C4A C5A C6A C7A -173.4(2) . . . . ? O1A C1A C6A C5A 177.75(19) . . . . ? C2A C1A C6A C5A -6.5(3) . . . . ? O1A C1A C6A C7A -6.5(3) . . . . ? C2A C1A C6A C7A 169.25(19) . . . . ? C5A C6A C7A O8A 102.3(3) . . . . ? C1A C6A C7A O8A -73.3(3) . . . . ? C6A C7A O8A C9A -74.7(3) . . . . ? C7A O8A C9A C2B 135.9(2) . . . . ? C1A O1A C11A C12A 110.4(3) . . . . ? O1A C11A C12A O12A -94.6(5) . . . . ? O1A C11A C12A N13A 84.6(3) . . . . ? O12A C12A N13A C14A -3.4(6) . . . . ? C11A C12A N13A C14A 177.5(3) . . . . ? C12A N13A C14A C15A 9.1(5) . . . . ? C12A N13A C14A C19A -171.5(3) . . . . ? C19A C14A C15A C16A 1.7(4) . . . . ? N13A C14A C15A C16A -178.9(3) . . . . ? C14A C15A C16A C17A -2.1(5) . . . . ? C15A C16A C17A C18A 1.1(5) . . . . ? C15A C16A C17A C71A 179.1(3) . . . . ? C16A C17A C18A C19A 0.1(5) . . . . ? C71A C17A C18A C19A -177.9(3) . . . . ? C17A C18A C19A C14A -0.4(5) . . . . ? C15A C14A C19A C18A -0.5(4) . . . . ? N13A C14A C19A C18A -179.9(3) . . . . ? C3A C4A C41A C48A -63.8(10) . . . . ? C5A C4A C41A C48A 118.7(10) . . . . ? C3A C4A C41A C43A 120.0(5) . . . . ? C5A C4A C41A C43A -57.5(6) . . . . ? C3A C4A C41A C42A -4.1(7) . . . . ? C5A C4A C41A C42A 178.4(7) . . . . ? C3A C4A C41A C44A -119.9(7) . . . . ? C5A C4A C41A C44A 62.6(7) . . . . ? C3A C4A C41A C46A 67.7(9) . . . . ? C5A C4A C41A C46A -109.8(9) . . . . ? C3A C4A C41A C47A -173.7(8) . . . . ? C5A C4A C41A C47A 8.8(8) . . . . ? C16A C17A C71A F73A 139.8(5) . . . . ? C18A C17A C71A F73A -42.2(6) . . . . ? C16A C17A C71A F74A -98.6(5) . . . . ? C18A C17A C71A F74A 79.4(6) . . . . ? C16A C17A C71A F72A 19.3(6) . . . . ? C18A C17A C71A F72A -162.7(4) . . . . ? C11B O1B C1B C2B 91.0(2) . . . . ? C11B O1B C1B C6B -91.4(2) . . . . ? O1B C1B C2B C3B -177.24(17) . . . . ? C6B C1B C2B C3B 5.3(3) . . . . ? O1B C1B C2B C9A 1.3(3) . . . . ? C6B C1B C2B C9A -176.19(18) . . . . ? O8A C9A C2B C3B -121.8(2) . . . . ? O8A C9A C2B C1B 59.6(3) . . . . ? C1B C2B C3B C4B 0.1(3) . . . . ? C9A C2B C3B C4B -178.4(2) . . . . ? C2B C3B C4B C5B -4.8(3) . . . . ? C2B C3B C4B C41B 176.5(2) . . . . ? C3B C4B C5B C6B 4.4(3) . . . . ? C41B C4B C5B C6B -177.0(2) . . . . ? C4B C5B C6B C1B 0.7(3) . . . . ? C4B C5B C6B C7B -178.9(2) . . . . ? C2B C1B C6B C5B -5.7(3) . . . . ? O1B C1B C6B C5B 176.86(18) . . . . ? C2B C1B C6B C7B 174.00(19) . . . . ? O1B C1B C6B C7B -3.5(3) . . . . ? C5B C6B C7B O8B 114.2(2) . . . . ? C1B C6B C7B O8B -65.4(3) . . . . ? C6B C7B O8B C9B -96.1(2) . . . . ? C7B O8B C9B C2C 64.0(3) . . . . ? C1B O1B C11B C12B -141.6(2) . . . . ? O1B C11B C12B O12B -166.3(3) . . . . ? O1B C11B C12B N13B 14.3(3) . . . . ? O12B C12B N13B C14B 5.4(5) . . . . ? C11B C12B N13B C14B -175.2(3) . . . . ? C12B N13B C14B C15B 3.4(5) . . . . ? C12B N13B C14B C19B -178.5(3) . . . . ? C19B C14B C15B C16B -0.8(5) . . . . ? N13B C14B C15B C16B 177.2(3) . . . . ? C14B C15B C16B C17B 0.3(6) . . . . ? C15B C16B C17B C18B 0.4(6) . . . . ? C15B C16B C17B C71B -177.1(3) . . . . ? C16B C17B C18B C19B -0.6(6) . . . . ? C71B C17B C18B C19B 176.9(4) . . . . ? C15B C14B C19B C18B 0.6(6) . . . . ? N13B C14B C19B C18B -177.5(4) . . . . ? C17B C18B C19B C14B 0.1(6) . . . . ? C5B C4B C41B C42B 14.8(3) . . . . ? C3B C4B C41B C42B -166.6(2) . . . . ? C5B C4B C41B C43B -106.0(3) . . . . ? C3B C4B C41B C43B 72.6(3) . . . . ? C5B C4B C41B C44B 134.9(3) . . . . ? C3B C4B C41B C44B -46.6(3) . . . . ? C16B C17B C71B F73B -42.2(5) . . . . ? C18B C17B C71B F73B 140.3(4) . . . . ? C16B C17B C71B F74B 82.5(4) . . . . ? C18B C17B C71B F74B -95.0(4) . . . . ? C16B C17B C71B F72B -161.2(3) . . . . ? C18B C17B C71B F72B 21.3(5) . . . . ? C11C O1C C1C C2C 92.9(2) . . . . ? C11C O1C C1C C6C -88.2(2) . . . . ? O1C C1C C2C C3C -179.96(19) . . . . ? C6C C1C C2C C3C 1.1(3) . . . . ? O1C C1C C2C C9B -1.0(3) . . . . ? C6C C1C C2C C9B -179.9(2) . . . . ? O8B C9B C2C C3C -132.4(2) . . . . ? O8B C9B C2C C1C 48.6(3) . . . . ? C1C C2C C3C C4C 1.0(3) . . . . ? C9B C2C C3C C4C -178.0(2) . . . . ? C2C C3C C4C C5C -1.9(3) . . . . ? C2C C3C C4C C41C 178.2(2) . . . . ? C3C C4C C5C C6C 0.8(3) . . . . ? C41C C4C C5C C6C -179.3(2) . . . . ? C4C C5C C6C C1C 1.2(3) . . . . ? C4C C5C C6C C7C -173.2(2) . . . . ? O1C C1C C6C C5C 178.89(18) . . . . ? C2C C1C C6C C5C -2.1(3) . . . . ? O1C C1C C6C C7C -6.8(3) . . . . ? C2C C1C C6C C7C 172.2(2) . . . . ? C5C C6C C7C O8C -111.7(2) . . . . ? C1C C6C C7C O8C 74.1(2) . . . . ? C6C C7C O8C C9C 173.79(18) . . . . ? C7C O8C C9C C2A 54.6(3) . . . . ? C1A C2A C9C O8C 57.1(3) . . . . ? C3A C2A C9C O8C -116.4(2) . . . . ? C1C O1C C11C C12C -151.76(19) . . . . ? O1C C11C C12C O12C -157.0(2) . . . . ? O1C C11C C12C N13C 26.4(3) . . . . ? O12C C12C N13C C14C 1.4(4) . . . . ? C11C C12C N13C C14C 177.7(2) . . . . ? C12C N13C C14C C15C 18.6(4) . . . . ? C12C N13C C14C C19C -164.4(3) . . . . ? C19C C14C C15C C16C 2.6(5) . . . . ? N13C C14C C15C C16C 179.6(3) . . . . ? C14C C15C C16C C17C -0.7(6) . . . . ? C15C C16C C17C C18C -2.1(6) . . . . ? C15C C16C C17C C71C 179.7(4) . . . . ? C16C C17C C18C C19C 3.0(5) . . . . ? C71C C17C C18C C19C -178.7(3) . . . . ? C17C C18C C19C C14C -1.1(4) . . . . ? C15C C14C C19C C18C -1.7(4) . . . . ? N13C C14C C19C C18C -178.8(2) . . . . ? C5C C4C C41C C44C -127.0(3) . . . . ? C3C C4C C41C C44C 52.9(3) . . . . ? C5C C4C C41C C42C -6.6(3) . . . . ? C3C C4C C41C C42C 173.3(3) . . . . ? C5C C4C C41C C43C 112.4(3) . . . . ? C3C C4C C41C C43C -67.7(3) . . . . ? C16C C17C C71C F74C 123.5(4) . . . . ? C18C C17C C71C F74C -54.8(5) . . . . ? C16C C17C C71C F72C -0.6(6) . . . . ? C18C C17C C71C F72C -178.9(4) . . . . ? C16C C17C C71C F73C -120.3(4) . . . . ? C18C C17C C71C F73C 61.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.244 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.036 # Attachment 'cr7b1.cif' data_cr7b _database_code_depnum_ccdc_archive 'CCDC 816687' #TrackingRef 'cr7b1.cif' _audit_creation_method 'SHELXL-97 and CrysAlisPro RED' _chemical_name_systematic ; ? ; _chemical_name_common Cone-5c _chemical_melting_point ? _chemical_formula_structural 'calixarene (C6H2OCH2CONHC6H4F-2,-tBu-5,-CH2OCH2-3-)3' _chemical_formula_moiety 'C60 H66 F3 N3 O9' _chemical_formula_sum 'C60 H66 F3 N3 O9' _chemical_formula_weight 1030.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.411(4) _cell_length_b 15.482(5) _cell_length_c 16.504(7) _cell_angle_alpha 92.63(3) _cell_angle_beta 97.69(3) _cell_angle_gamma 106.65(3) _cell_volume 2757.3(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 1.0 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1092 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 1.045 _exptl_absorpt_process_details ; CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.32.24 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur 3/CCD' _diffrn_measurement_method 'Thin slice \f and \w scans' _diffrn_detector_area_resol_mean 16.0050 _diffrn_reflns_number 10289 _diffrn_reflns_av_R_equivalents 0.1052 _diffrn_reflns_av_sigmaI/netI 0.0964 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 20.00 _reflns_number_total 4076 _reflns_number_gt 2772 _reflns_threshold_expression I>2sigma(I) _computing_data_collection ; CrysAlisPro CCD, Oxford Diffraction Ltd., Version 1.171.32.24 ; _computing_cell_refinement ; CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.32.24 ; _computing_data_reduction ; CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.32.24 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP (Johnson, 1971)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4076 _refine_ls_number_parameters 571 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3008 _refine_ls_R_factor_gt 0.2672 _refine_ls_wR_factor_ref 0.5898 _refine_ls_wR_factor_gt 0.5722 _refine_ls_goodness_of_fit_ref 2.321 _refine_ls_restrained_S_all 2.321 _refine_ls_shift/su_max 0.178 _refine_ls_shift/su_mean 0.017 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 O1A O 0.4118(16) 0.1729(10) 0.6284(9) 0.071(5) Uani 1 1 d . . . C1A C 0.367(2) 0.1359(16) 0.7006(14) 0.062(7) Uiso 1 1 d . . . C2A C 0.268(2) 0.0691(15) 0.6886(13) 0.056(6) Uiso 1 1 d . . . C3A C 0.228(2) 0.0234(16) 0.7554(16) 0.079(8) Uani 1 1 d . . . H3A H 0.1617 -0.0293 0.7455 0.094 Uiso 1 1 calc R . . C4A C 0.283(3) 0.0531(18) 0.8358(15) 0.091(10) Uani 1 1 d . . . C5A C 0.390(2) 0.1264(17) 0.8435(13) 0.061(7) Uani 1 1 d . . . H5A H 0.4323 0.1490 0.8958 0.074 Uiso 1 1 calc R . . C6A C 0.436(2) 0.1670(17) 0.7761(14) 0.064(7) Uiso 1 1 d . . . C7A C 0.542(3) 0.255(2) 0.7944(17) 0.098(9) Uani 1 1 d . . . H7A1 H 0.5722 0.2634 0.8529 0.118 Uiso 1 1 calc R . . H7A2 H 0.6096 0.2490 0.7665 0.118 Uiso 1 1 calc R . . O8A O 0.5068(18) 0.3336(11) 0.7690(9) 0.071(5) Uani 1 1 d . . . C9A C 0.397(3) 0.341(2) 0.7900(14) 0.079(9) Uani 1 1 d . . . H9A1 H 0.3963 0.3331 0.8480 0.095 Uiso 1 1 calc R . . H9A2 H 0.3286 0.2931 0.7592 0.095 Uiso 1 1 calc R . . C11A C 0.542(3) 0.186(2) 0.6180(15) 0.092(9) Uani 1 1 d . . . H11A H 0.5777 0.1520 0.6574 0.110 Uiso 1 1 calc R . . H11B H 0.5875 0.2493 0.6306 0.110 Uiso 1 1 calc R . . C12A C 0.560(5) 0.155(3) 0.529(2) 0.126(12) Uiso 1 1 d . . . O12A O 0.664(2) 0.150(2) 0.5214(10) 0.176(13) Uani 1 1 d . . . N13A N 0.455(2) 0.1166(15) 0.4811(13) 0.090(7) Uani 1 1 d . . . H13A H 0.3881 0.1110 0.5019 0.108 Uiso 1 1 calc R . . C14A C 0.442(3) 0.0827(19) 0.3945(19) 0.090(8) Uiso 1 1 d . . . C15A C 0.332(3) 0.016(2) 0.3688(18) 0.107(10) Uiso 1 1 d . . . H15A H 0.2746 -0.0048 0.4038 0.129 Uiso 1 1 calc R . . C16A C 0.310(3) -0.021(3) 0.2783(17) 0.135(13) Uani 1 1 d . . . H16A H 0.2363 -0.0592 0.2498 0.162 Uiso 1 1 calc R . . C17A C 0.418(4) 0.011(3) 0.246(2) 0.114(11) Uiso 1 1 d . . . F17A F 0.384(2) -0.0347(15) 0.1607(12) 0.169(9) Uani 1 1 d . . . C18A C 0.514(3) 0.068(2) 0.2682(19) 0.094(9) Uiso 1 1 d . . . H18A H 0.5724 0.0877 0.2337 0.112 Uiso 1 1 calc R . . C19A C 0.530(3) 0.102(2) 0.3473(18) 0.100(9) Uani 1 1 d . . . H19A H 0.6075 0.1408 0.3699 0.120 Uiso 1 1 calc R . . C41A C 0.238(3) 0.007(2) 0.9080(18) 0.084(9) Uani 1 1 d . . . C42A C 0.292(5) -0.056(4) 0.932(3) 0.22(2) Uiso 1 1 d . . . H42A H 0.2817 -0.1003 0.8874 0.329 Uiso 1 1 calc R . . H42B H 0.2555 -0.0845 0.9769 0.329 Uiso 1 1 calc R . . H42C H 0.3792 -0.0272 0.9502 0.329 Uiso 1 1 calc R . . C43A C 0.273(7) 0.062(3) 0.986(3) 0.28(4) Uani 1 1 d . . . H43A H 0.2522 0.1173 0.9792 0.426 Uiso 1 1 calc R . . H43B H 0.3601 0.0750 1.0033 0.426 Uiso 1 1 calc R . . H43C H 0.2286 0.0296 1.0261 0.426 Uiso 1 1 calc R . . C44A C 0.107(7) -0.049(5) 0.888(5) 0.31(4) Uiso 1 1 d . . . H44A H 0.0555 -0.0103 0.8794 0.461 Uiso 1 1 calc R . . H44B H 0.0850 -0.0850 0.9325 0.461 Uiso 1 1 calc R . . H44C H 0.0968 -0.0881 0.8389 0.461 Uiso 1 1 calc R . . O1B O 0.3258(16) 0.3793(10) 0.6270(9) 0.073(5) Uani 1 1 d . . . C1B C 0.340(2) 0.4454(18) 0.6942(15) 0.069(7) Uiso 1 1 d . . . C2B C 0.382(3) 0.4346(17) 0.7714(13) 0.083(9) Uani 1 1 d . . . C3B C 0.3883(17) 0.4955(13) 0.8357(12) 0.039(5) Uiso 1 1 d . . . H3B H 0.4123 0.4834 0.8890 0.046 Uiso 1 1 calc R . . C4B C 0.359(2) 0.5756(14) 0.8218(12) 0.052(6) Uiso 1 1 d . . . C5B C 0.3108(18) 0.5862(14) 0.7428(12) 0.045(6) Uiso 1 1 d . . . H5B H 0.2881 0.6380 0.7312 0.054 Uiso 1 1 calc R . . C6B C 0.2963(19) 0.5176(15) 0.6805(13) 0.056(6) Uani 1 1 d . . . C7B C 0.238(2) 0.5336(14) 0.5903(12) 0.052(6) Uiso 1 1 d . . . H7B1 H 0.2094 0.5869 0.5939 0.063 Uiso 1 1 calc R . . H7B2 H 0.3014 0.5450 0.5553 0.063 Uiso 1 1 calc R . . O8B O 0.1352(14) 0.4572(10) 0.5533(8) 0.068(5) Uani 1 1 d . . . C9B C 0.031(2) 0.4337(18) 0.5983(13) 0.068(8) Uani 1 1 d . . . H9B1 H 0.0370 0.4848 0.6366 0.082 Uiso 1 1 calc R . . H9B2 H -0.0449 0.4223 0.5601 0.082 Uiso 1 1 calc R . . C11B C 0.441(3) 0.4050(18) 0.5990(15) 0.086(9) Uani 1 1 d . . . H11C H 0.5038 0.3908 0.6375 0.103 Uiso 1 1 calc R . . H11D H 0.4673 0.4696 0.5936 0.103 Uiso 1 1 calc R . . C12B C 0.425(4) 0.3495(18) 0.5110(19) 0.074(8) Uani 1 1 d . . . O12B O 0.523(2) 0.3628(15) 0.4845(11) 0.113(8) Uani 1 1 d . . . N13B N 0.317(2) 0.3059(15) 0.4749(9) 0.066(7) Uani 1 1 d . . . H13B H 0.2577 0.3041 0.5025 0.079 Uiso 1 1 calc R . . C14B C 0.283(2) 0.2609(15) 0.3973(14) 0.050(6) Uani 1 1 d . . . C15B C 0.349(3) 0.289(2) 0.3338(17) 0.096(9) Uani 1 1 d . . . H15B H 0.4215 0.3373 0.3455 0.116 Uiso 1 1 calc R . . C16B C 0.311(4) 0.248(3) 0.2510(18) 0.153(16) Uani 1 1 d . . . H16B H 0.3465 0.2739 0.2070 0.184 Uiso 1 1 calc R . . C17B C 0.217(3) 0.1677(19) 0.2420(17) 0.076(8) Uiso 1 1 d . . . F17B F 0.178(2) 0.137(2) 0.1631(10) 0.210(12) Uani 1 1 d . . . C18B C 0.140(3) 0.140(2) 0.3020(14) 0.122(13) Uani 1 1 d . . . H18B H 0.0648 0.0943 0.2892 0.147 Uiso 1 1 calc R . . C19B C 0.180(3) 0.182(2) 0.3804(19) 0.104(10) Uani 1 1 d . . . H19B H 0.1388 0.1586 0.4230 0.125 Uiso 1 1 calc R . . C41B C 0.386(3) 0.648(2) 0.8969(14) 0.103(11) Uani 1 1 d . . . C42B C 0.391(4) 0.734(2) 0.866(3) 0.19(2) Uani 1 1 d . . . H42D H 0.3136 0.7304 0.8331 0.279 Uiso 1 1 calc R . . H42E H 0.4563 0.7503 0.8332 0.279 Uiso 1 1 calc R . . H42F H 0.4072 0.7796 0.9112 0.279 Uiso 1 1 calc R . . C43B C 0.263(5) 0.619(4) 0.938(4) 0.34(5) Uani 1 1 d . . . H43D H 0.2550 0.5614 0.9597 0.508 Uiso 1 1 calc R . . H43E H 0.1921 0.6144 0.8976 0.508 Uiso 1 1 calc R . . H43F H 0.2673 0.6635 0.9819 0.508 Uiso 1 1 calc R . . C44B C 0.498(5) 0.652(3) 0.952(2) 0.21(2) Uani 1 1 d . . . H44D H 0.4889 0.5946 0.9739 0.308 Uiso 1 1 calc R . . H44E H 0.5108 0.6980 0.9965 0.308 Uiso 1 1 calc R . . H44F H 0.5669 0.6664 0.9229 0.308 Uiso 1 1 calc R . . O1C O 0.0390(15) 0.2634(12) 0.5217(8) 0.082(6) Uani 1 1 d . . . C1C C 0.031(2) 0.2719(15) 0.6077(14) 0.058(7) Uani 1 1 d . . . C2C C 0.027(2) 0.3570(16) 0.6421(13) 0.054(6) Uiso 1 1 d . . . C3C C 0.026(2) 0.3574(17) 0.7312(15) 0.075(8) Uani 1 1 d . . . H3C H 0.0279 0.4104 0.7610 0.090 Uiso 1 1 calc R . . C4C C 0.0224(18) 0.279(2) 0.7723(15) 0.062(8) Uani 1 1 d . . . C5C C 0.024(2) 0.2010(16) 0.7317(14) 0.063(7) Uani 1 1 d . . . H5C H 0.0238 0.1506 0.7605 0.075 Uiso 1 1 calc R . . C6C C 0.0272(19) 0.1954(15) 0.6450(12) 0.045(6) Uiso 1 1 d . . . C7C C 0.027(2) 0.1062(17) 0.6107(16) 0.072(8) Uani 1 1 d . . . H7C1 H 0.0209 0.0653 0.6539 0.086 Uiso 1 1 calc R . . H7C2 H -0.0448 0.0820 0.5689 0.086 Uiso 1 1 calc R . . O8C O 0.1382(17) 0.1096(13) 0.5749(8) 0.080(5) Uani 1 1 d . . . C9C C 0.186(2) 0.038(2) 0.5969(14) 0.078(8) Uani 1 1 d . . . H9C1 H 0.2385 0.0270 0.5580 0.093 Uiso 1 1 calc R . . H9C2 H 0.1198 -0.0176 0.5976 0.093 Uiso 1 1 calc R . . C11C C -0.075(2) 0.2429(15) 0.4711(13) 0.061(7) Uiso 1 1 d . . . H11E H -0.1268 0.2743 0.4943 0.074 Uiso 1 1 calc R . . H11F H -0.1159 0.1784 0.4685 0.074 Uiso 1 1 calc R . . C12C C -0.060(2) 0.2705(16) 0.3838(13) 0.051(6) Uiso 1 1 d . . . O12C O -0.1411(16) 0.2321(14) 0.3258(9) 0.115(8) Uani 1 1 d . . . N13C N 0.0275(17) 0.3451(13) 0.3813(9) 0.067(6) Uani 1 1 d . . . H13C H 0.0567 0.3782 0.4270 0.080 Uiso 1 1 calc R . . C14C C 0.081(3) 0.378(2) 0.3112(17) 0.082(8) Uiso 1 1 d . . . C15C C 0.030(2) 0.3445(19) 0.2351(15) 0.088(9) Uani 1 1 d . . . H15C H -0.0438 0.2979 0.2269 0.106 Uiso 1 1 calc R . . C16C C 0.085(5) 0.376(3) 0.1652(18) 0.18(2) Uani 1 1 d . . . H16C H 0.0568 0.3463 0.1129 0.212 Uiso 1 1 calc R . . C17C C 0.187(3) 0.458(3) 0.1825(18) 0.110(11) Uani 1 1 d . . . F17C F 0.244(2) 0.4872(18) 0.1143(11) 0.193(11) Uani 1 1 d . . . C18C C 0.237(3) 0.494(2) 0.2603(18) 0.123(12) Uani 1 1 d . . . H18C H 0.3078 0.5434 0.2706 0.148 Uiso 1 1 calc R . . C19C C 0.179(3) 0.4559(19) 0.3238(14) 0.093(10) Uani 1 1 d . . . H19C H 0.2076 0.4835 0.3769 0.112 Uiso 1 1 calc R . . C41C C 0.020(3) 0.2891(16) 0.8679(15) 0.073(8) Uani 1 1 d . . . C42C C 0.139(4) 0.283(5) 0.9192(18) 0.27(4) Uani 1 1 d . . . H42G H 0.2082 0.3298 0.9069 0.411 Uiso 1 1 calc R . . H42H H 0.1499 0.2249 0.9064 0.411 Uiso 1 1 calc R . . H42I H 0.1329 0.2901 0.9765 0.411 Uiso 1 1 calc R . . C43C C -0.091(4) 0.217(3) 0.8839(18) 0.20(2) Uani 1 1 d . . . H43G H -0.0814 0.1585 0.8705 0.303 Uiso 1 1 calc R . . H43H H -0.1636 0.2227 0.8507 0.303 Uiso 1 1 calc R . . H43I H -0.0993 0.2228 0.9409 0.303 Uiso 1 1 calc R . . C44C C -0.014(4) 0.379(3) 0.8951(18) 0.171(18) Uani 1 1 d . . . H44G H 0.0505 0.4312 0.8868 0.257 Uiso 1 1 calc R . . H44H H -0.0236 0.3791 0.9521 0.257 Uiso 1 1 calc R . . H44I H -0.0906 0.3789 0.8627 0.257 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 O1A 0.061(14) 0.077(12) 0.070(11) 0.009(8) 0.004(9) 0.014(9) C3A 0.10(2) 0.051(16) 0.08(2) 0.014(14) 0.021(16) 0.014(15) C4A 0.16(3) 0.065(19) 0.037(16) 0.000(14) 0.042(17) 0.00(2) C5A 0.045(17) 0.075(19) 0.051(15) 0.010(12) 0.005(12) -0.003(15) C7A 0.08(2) 0.11(3) 0.10(2) 0.015(18) 0.007(16) 0.03(2) O8A 0.066(14) 0.057(11) 0.085(12) -0.002(9) 0.008(10) 0.013(10) C9A 0.04(2) 0.14(3) 0.050(15) -0.030(15) 0.015(13) 0.010(17) C11A 0.05(2) 0.14(3) 0.070(18) 0.003(16) -0.005(15) 0.024(18) O12A 0.063(16) 0.41(4) 0.042(11) 0.016(16) 0.030(10) 0.049(19) N13A 0.068(18) 0.114(19) 0.073(15) 0.008(13) 0.032(13) -0.008(14) C16A 0.10(3) 0.20(4) 0.07(2) -0.04(2) -0.029(19) 0.03(3) F17A 0.21(2) 0.19(2) 0.122(16) -0.030(14) -0.016(14) 0.096(18) C19A 0.09(2) 0.14(3) 0.09(2) 0.001(18) 0.037(18) 0.06(2) C41A 0.10(2) 0.09(2) 0.10(2) 0.051(18) 0.024(18) 0.065(19) C43A 0.63(12) 0.08(3) 0.14(4) 0.04(3) 0.21(5) 0.02(4) O1B 0.064(13) 0.065(11) 0.068(10) -0.010(9) -0.002(9) -0.007(10) C2B 0.14(3) 0.070(18) 0.035(14) -0.002(12) -0.038(14) 0.048(18) C6B 0.028(15) 0.062(16) 0.079(16) 0.015(13) 0.012(12) 0.013(12) O8B 0.069(12) 0.074(11) 0.042(9) 0.017(8) 0.013(8) -0.010(9) C9B 0.056(19) 0.12(2) 0.038(13) 0.041(14) 0.003(13) 0.030(15) C11B 0.09(3) 0.08(2) 0.074(19) 0.005(15) 0.029(17) -0.007(17) C12B 0.06(3) 0.058(18) 0.12(3) 0.016(17) 0.04(2) 0.021(17) O12B 0.054(15) 0.17(2) 0.090(14) -0.004(12) 0.023(12) -0.010(13) N13B 0.028(16) 0.143(19) 0.016(11) 0.008(11) -0.010(9) 0.016(14) C14B 0.048(18) 0.042(15) 0.064(18) -0.001(12) 0.014(15) 0.018(14) C15B 0.09(2) 0.14(3) 0.07(2) 0.004(18) 0.046(18) 0.026(19) C16B 0.15(3) 0.26(5) 0.05(2) 0.00(2) 0.05(2) 0.05(3) F17B 0.19(2) 0.32(3) 0.070(12) -0.087(16) -0.010(12) 0.03(2) C18B 0.10(3) 0.19(3) 0.027(15) 0.006(17) -0.025(15) -0.02(2) C19B 0.09(3) 0.12(3) 0.10(3) 0.03(2) 0.008(19) 0.04(2) C41B 0.19(4) 0.11(3) 0.026(14) 0.000(14) 0.034(19) 0.08(2) C42B 0.26(5) 0.05(2) 0.23(5) -0.04(3) -0.02(4) 0.07(3) C43B 0.27(6) 0.32(7) 0.33(7) -0.20(6) 0.26(6) -0.14(6) C44B 0.32(6) 0.19(4) 0.07(2) -0.05(2) -0.10(3) 0.09(4) O1C 0.093(14) 0.136(16) 0.030(9) 0.024(9) -0.005(8) 0.058(12) C1C 0.050(17) 0.053(16) 0.065(16) 0.026(12) -0.011(12) 0.012(12) C3C 0.07(2) 0.074(19) 0.079(18) -0.023(15) 0.051(14) 0.004(15) C4C 0.015(15) 0.08(2) 0.079(19) 0.064(17) -0.002(12) -0.005(13) C5C 0.08(2) 0.023(14) 0.084(18) 0.008(13) 0.006(14) 0.017(13) C7C 0.026(17) 0.09(2) 0.100(19) 0.028(16) 0.027(15) 0.013(14) O8C 0.090(15) 0.123(16) 0.041(9) 0.026(9) 0.030(9) 0.040(12) C9C 0.08(2) 0.10(2) 0.053(15) 0.005(14) 0.015(14) 0.025(18) O12C 0.067(14) 0.19(2) 0.053(11) 0.016(11) -0.020(9) -0.012(13) N13C 0.070(15) 0.084(15) 0.024(9) 0.000(9) 0.003(9) -0.011(12) C15C 0.06(2) 0.13(2) 0.051(17) 0.018(15) -0.046(14) 0.015(16) C16C 0.29(5) 0.13(3) 0.033(19) -0.006(18) -0.01(2) -0.05(3) C17C 0.11(3) 0.17(4) 0.05(2) 0.01(2) 0.034(19) 0.05(3) F17C 0.19(2) 0.29(3) 0.088(13) 0.101(15) 0.060(14) 0.015(19) C18C 0.12(3) 0.17(3) 0.05(2) -0.01(2) 0.027(19) 0.00(2) C19C 0.12(3) 0.12(2) 0.031(14) 0.004(14) 0.045(15) 0.00(2) C41C 0.09(2) 0.033(15) 0.073(19) 0.013(13) 0.034(17) -0.023(14) C42C 0.15(4) 0.61(11) 0.024(18) 0.05(3) -0.01(2) 0.06(5) C43C 0.25(5) 0.29(6) 0.05(2) 0.01(3) 0.10(3) 0.01(4) C44C 0.26(5) 0.17(4) 0.06(2) 0.01(2) -0.02(2) 0.03(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1A C1A 1.44(3) . ? O1A C11A 1.48(3) . ? C1A C2A 1.28(3) . ? C1A C6A 1.37(3) . ? C2A C3A 1.39(3) . ? C2A C9C 1.64(3) . ? C3A C4A 1.39(3) . ? C3A H3A 0.9300 . ? C4A C5A 1.40(3) . ? C4A C41A 1.49(3) . ? C5A C6A 1.39(3) . ? C5A H5A 0.9300 . ? C6A C7A 1.52(3) . ? C7A O8A 1.46(3) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? O8A C9A 1.37(3) . ? C9A C2B 1.55(3) . ? C9A H9A1 0.9700 . ? C9A H9A2 0.9700 . ? C11A C12A 1.59(4) . ? C11A H11A 0.9700 . ? C11A H11B 0.9700 . ? C12A O12A 1.23(4) . ? C12A N13A 1.30(4) . ? N13A C14A 1.47(3) . ? N13A H13A 0.8600 . ? C14A C19A 1.33(4) . ? C14A C15A 1.38(4) . ? C15A C16A 1.54(4) . ? C15A H15A 0.9300 . ? C16A C17A 1.37(4) . ? C16A H16A 0.9300 . ? C17A C18A 1.19(4) . ? C17A F17A 1.50(4) . ? C18A C19A 1.35(4) . ? C18A H18A 0.9300 . ? C19A H19A 0.9300 . ? C41A C42A 1.34(5) . ? C41A C43A 1.45(5) . ? C41A C44A 1.48(7) . ? C42A H42A 0.9600 . ? C42A H42B 0.9600 . ? C42A H42C 0.9600 . ? C43A H43A 0.9600 . ? C43A H43B 0.9600 . ? C43A H43C 0.9600 . ? C44A H44A 0.9600 . ? C44A H44B 0.9600 . ? C44A H44C 0.9600 . ? O1B C11B 1.41(3) . ? O1B C1B 1.43(3) . ? C1B C2B 1.33(3) . ? C1B C6B 1.36(3) . ? C2B C3B 1.37(3) . ? C3B C4B 1.39(3) . ? C3B H3B 0.9300 . ? C4B C5B 1.38(2) . ? C4B C41B 1.57(3) . ? C5B C6B 1.40(3) . ? C5B H5B 0.9300 . ? C6B C7B 1.61(3) . ? C7B O8B 1.45(2) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? O8B C9B 1.45(2) . ? C9B C2C 1.41(3) . ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? C11B C12B 1.61(4) . ? C11B H11C 0.9700 . ? C11B H11D 0.9700 . ? C12B O12B 1.22(3) . ? C12B N13B 1.27(3) . ? N13B C14B 1.38(3) . ? N13B H13B 0.8600 . ? C14B C15B 1.39(3) . ? C14B C19B 1.41(3) . ? C15B C16B 1.44(4) . ? C15B H15B 0.9300 . ? C16B C17B 1.38(4) . ? C16B H16B 0.9300 . ? C17B F17B 1.34(3) . ? C17B C18B 1.41(4) . ? C18B C19B 1.38(4) . ? C18B H18B 0.9300 . ? C19B H19B 0.9300 . ? C41B C42B 1.43(4) . ? C41B C44B 1.45(4) . ? C41B C43B 1.60(5) . ? C42B H42D 0.9600 . ? C42B H42E 0.9600 . ? C42B H42F 0.9600 . ? C43B H43D 0.9600 . ? C43B H43E 0.9600 . ? C43B H43F 0.9600 . ? C44B H44D 0.9600 . ? C44B H44E 0.9600 . ? C44B H44F 0.9600 . ? O1C C11C 1.39(3) . ? O1C C1C 1.44(3) . ? C1C C6C 1.35(3) . ? C1C C2C 1.43(3) . ? C2C C3C 1.47(3) . ? C3C C4C 1.41(3) . ? C3C H3C 0.9300 . ? C4C C5C 1.36(3) . ? C4C C41C 1.58(3) . ? C5C C6C 1.43(3) . ? C5C H5C 0.9300 . ? C6C C7C 1.47(3) . ? C7C O8C 1.46(3) . ? C7C H7C1 0.9700 . ? C7C H7C2 0.9700 . ? O8C C9C 1.42(3) . ? C9C H9C1 0.9700 . ? C9C H9C2 0.9700 . ? C11C C12C 1.54(3) . ? C11C H11E 0.9700 . ? C11C H11F 0.9700 . ? C12C O12C 1.23(2) . ? C12C N13C 1.30(3) . ? N13C C14C 1.43(3) . ? N13C H13C 0.8600 . ? C14C C15C 1.33(3) . ? C14C C19C 1.37(3) . ? C15C C16C 1.42(4) . ? C15C H15C 0.9300 . ? C16C C17C 1.44(4) . ? C16C H16C 0.9300 . ? C17C C18C 1.36(4) . ? C17C F17C 1.40(3) . ? C18C C19C 1.38(3) . ? C18C H18C 0.9300 . ? C19C H19C 0.9300 . ? C41C C43C 1.49(4) . ? C41C C42C 1.53(5) . ? C41C C44C 1.61(5) . ? C42C H42G 0.9600 . ? C42C H42H 0.9600 . ? C42C H42I 0.9600 . ? C43C H43G 0.9600 . ? C43C H43H 0.9600 . ? C43C H43I 0.9600 . ? C44C H44G 0.9600 . ? C44C H44H 0.9600 . ? C44C H44I 0.9600 . ? 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 C1A O1A C11A 120.4(18) . . ? C2A C1A C6A 124(2) . . ? C2A C1A O1A 116(2) . . ? C6A C1A O1A 119(2) . . ? C1A C2A C3A 119(2) . . ? C1A C2A C9C 121(2) . . ? C3A C2A C9C 120(2) . . ? C4A C3A C2A 123(2) . . ? C4A C3A H3A 118.5 . . ? C2A C3A H3A 118.6 . . ? C3A C4A C5A 114(2) . . ? C3A C4A C41A 123(3) . . ? C5A C4A C41A 122(2) . . ? C6A C5A C4A 123(2) . . ? C6A C5A H5A 118.6 . . ? C4A C5A H5A 118.6 . . ? C1A C6A C5A 117(2) . . ? C1A C6A C7A 125(2) . . ? C5A C6A C7A 117(2) . . ? O8A C7A C6A 113(2) . . ? O8A C7A H7A1 108.9 . . ? C6A C7A H7A1 108.9 . . ? O8A C7A H7A2 109.0 . . ? C6A C7A H7A2 109.0 . . ? H7A1 C7A H7A2 107.8 . . ? C9A O8A C7A 116(2) . . ? O8A C9A C2B 110(2) . . ? O8A C9A H9A1 109.6 . . ? C2B C9A H9A1 109.6 . . ? O8A C9A H9A2 109.6 . . ? C2B C9A H9A2 109.7 . . ? H9A1 C9A H9A2 108.1 . . ? O1A C11A C12A 114(3) . . ? O1A C11A H11A 108.7 . . ? C12A C11A H11A 108.7 . . ? O1A C11A H11B 108.7 . . ? C12A C11A H11B 108.7 . . ? H11A C11A H11B 107.6 . . ? O12A C12A N13A 129(4) . . ? O12A C12A C11A 116(4) . . ? N13A C12A C11A 113(4) . . ? C12A N13A C14A 125(3) . . ? C12A N13A H13A 117.5 . . ? C14A N13A H13A 117.5 . . ? C19A C14A C15A 121(3) . . ? C19A C14A N13A 126(3) . . ? C15A C14A N13A 112(3) . . ? C14A C15A C16A 116(3) . . ? C14A C15A H15A 122.3 . . ? C16A C15A H15A 122.2 . . ? C17A C16A C15A 109(3) . . ? C17A C16A H16A 125.4 . . ? C15A C16A H16A 125.6 . . ? C18A C17A C16A 135(4) . . ? C18A C17A F17A 122(4) . . ? C16A C17A F17A 102(3) . . ? C17A C18A C19A 115(4) . . ? C17A C18A H18A 122.7 . . ? C19A C18A H18A 122.6 . . ? C14A C19A C18A 123(3) . . ? C14A C19A H19A 118.2 . . ? C18A C19A H19A 118.3 . . ? C42A C41A C43A 96(4) . . ? C42A C41A C44A 101(4) . . ? C43A C41A C44A 116(4) . . ? C42A C41A C4A 115(3) . . ? C43A C41A C4A 116(3) . . ? C44A C41A C4A 111(4) . . ? C41A C42A H42A 109.7 . . ? C41A C42A H42B 109.4 . . ? H42A C42A H42B 109.5 . . ? C41A C42A H42C 109.3 . . ? H42A C42A H42C 109.5 . . ? H42B C42A H42C 109.5 . . ? C41A C43A H43A 109.4 . . ? C41A C43A H43B 109.5 . . ? H43A C43A H43B 109.5 . . ? C41A C43A H43C 109.5 . . ? H43A C43A H43C 109.5 . . ? H43B C43A H43C 109.5 . . ? C41A C44A H44A 108.8 . . ? C41A C44A H44B 109.5 . . ? H44A C44A H44B 109.5 . . ? C41A C44A H44C 110.1 . . ? H44A C44A H44C 109.5 . . ? H44B C44A H44C 109.5 . . ? C11B O1B C1B 103.8(17) . . ? C2B C1B C6B 118(2) . . ? C2B C1B O1B 123(2) . . ? C6B C1B O1B 119(2) . . ? C1B C2B C3B 122(2) . . ? C1B C2B C9A 118(2) . . ? C3B C2B C9A 118.7(18) . . ? C2B C3B C4B 120.3(19) . . ? C2B C3B H3B 119.8 . . ? C4B C3B H3B 119.8 . . ? C5B C4B C3B 117.8(19) . . ? C5B C4B C41B 124(2) . . ? C3B C4B C41B 117.7(19) . . ? C4B C5B C6B 118.9(19) . . ? C4B C5B H5B 120.6 . . ? C6B C5B H5B 120.6 . . ? C1B C6B C5B 122(2) . . ? C1B C6B C7B 122(2) . . ? C5B C6B C7B 116.3(18) . . ? O8B C7B C6B 112.5(16) . . ? O8B C7B H7B1 109.1 . . ? C6B C7B H7B1 109.1 . . ? O8B C7B H7B2 109.1 . . ? C6B C7B H7B2 109.1 . . ? H7B1 C7B H7B2 107.8 . . ? C7B O8B C9B 115.1(16) . . ? C2C C9B O8B 112.9(19) . . ? C2C C9B H9B1 109.0 . . ? O8B C9B H9B1 109.0 . . ? C2C C9B H9B2 109.0 . . ? O8B C9B H9B2 109.0 . . ? H9B1 C9B H9B2 107.8 . . ? O1B C11B C12B 107(2) . . ? O1B C11B H11C 110.3 . . ? C12B C11B H11C 110.2 . . ? O1B C11B H11D 110.2 . . ? C12B C11B H11D 110.2 . . ? H11C C11B H11D 108.5 . . ? O12B C12B N13B 128(3) . . ? O12B C12B C11B 112(3) . . ? N13B C12B C11B 120(3) . . ? C12B N13B C14B 128(2) . . ? C12B N13B H13B 115.7 . . ? C14B N13B H13B 115.8 . . ? N13B C14B C15B 122(2) . . ? N13B C14B C19B 121(2) . . ? C15B C14B C19B 118(2) . . ? C14B C15B C16B 123(3) . . ? C14B C15B H15B 118.4 . . ? C16B C15B H15B 118.5 . . ? C17B C16B C15B 115(3) . . ? C17B C16B H16B 122.7 . . ? C15B C16B H16B 122.7 . . ? F17B C17B C16B 112(3) . . ? F17B C17B C18B 121(3) . . ? C16B C17B C18B 123(3) . . ? C19B C18B C17B 118(3) . . ? C19B C18B H18B 121.2 . . ? C17B C18B H18B 121.2 . . ? C18B C19B C14B 122(3) . . ? C18B C19B H19B 119.2 . . ? C14B C19B H19B 119.3 . . ? C42B C41B C44B 112(3) . . ? C42B C41B C4B 108(2) . . ? C44B C41B C4B 112(3) . . ? C42B C41B C43B 106(4) . . ? C44B C41B C43B 114(4) . . ? C4B C41B C43B 104(3) . . ? C41B C42B H42D 109.4 . . ? C41B C42B H42E 109.5 . . ? H42D C42B H42E 109.5 . . ? C41B C42B H42F 109.5 . . ? H42D C42B H42F 109.5 . . ? H42E C42B H42F 109.5 . . ? C41B C43B H43D 109.4 . . ? C41B C43B H43E 109.4 . . ? H43D C43B H43E 109.5 . . ? C41B C43B H43F 109.5 . . ? H43D C43B H43F 109.5 . . ? H43E C43B H43F 109.5 . . ? C41B C44B H44D 109.5 . . ? C41B C44B H44E 109.5 . . ? H44D C44B H44E 109.5 . . ? C41B C44B H44F 109.4 . . ? H44D C44B H44F 109.5 . . ? H44E C44B H44F 109.5 . . ? C11C O1C C1C 113.6(17) . . ? C6C C1C C2C 129(2) . . ? C6C C1C O1C 114(2) . . ? C2C C1C O1C 117.5(17) . . ? C9B C2C C1C 125(2) . . ? C9B C2C C3C 124(2) . . ? C1C C2C C3C 111(2) . . ? C4C C3C C2C 121(2) . . ? C4C C3C H3C 119.3 . . ? C2C C3C H3C 119.3 . . ? C5C C4C C3C 121(2) . . ? C5C C4C C41C 123(2) . . ? C3C C4C C41C 116(2) . . ? C4C C5C C6C 121(2) . . ? C4C C5C H5C 119.6 . . ? C6C C5C H5C 119.6 . . ? C1C C6C C5C 116(2) . . ? C1C C6C C7C 130(2) . . ? C5C C6C C7C 114(2) . . ? O8C C7C C6C 112.7(19) . . ? O8C C7C H7C1 109.0 . . ? C6C C7C H7C1 109.1 . . ? O8C C7C H7C2 109.0 . . ? C6C C7C H7C2 109.1 . . ? H7C1 C7C H7C2 107.8 . . ? C9C O8C C7C 111.9(18) . . ? O8C C9C C2A 106.2(19) . . ? O8C C9C H9C1 110.5 . . ? C2A C9C H9C1 110.5 . . ? O8C C9C H9C2 110.5 . . ? C2A C9C H9C2 110.5 . . ? H9C1 C9C H9C2 108.7 . . ? O1C C11C C12C 111.5(19) . . ? O1C C11C H11E 109.3 . . ? C12C C11C H11E 109.3 . . ? O1C C11C H11F 109.3 . . ? C12C C11C H11F 109.3 . . ? H11E C11C H11F 108.0 . . ? O12C C12C N13C 125(2) . . ? O12C C12C C11C 119(2) . . ? N13C C12C C11C 114.0(19) . . ? C12C N13C C14C 127(2) . . ? C12C N13C H13C 116.5 . . ? C14C N13C H13C 116.4 . . ? C15C C14C C19C 119(3) . . ? C15C C14C N13C 123(3) . . ? C19C C14C N13C 117(2) . . ? C14C C15C C16C 123(3) . . ? C14C C15C H15C 118.5 . . ? C16C C15C H15C 118.5 . . ? C15C C16C C17C 114(2) . . ? C15C C16C H16C 122.8 . . ? C17C C16C H16C 122.9 . . ? C18C C17C F17C 123(3) . . ? C18C C17C C16C 122(3) . . ? F17C C17C C16C 114(3) . . ? C17C C18C C19C 118(3) . . ? C17C C18C H18C 120.8 . . ? C19C C18C H18C 121.0 . . ? C14C C19C C18C 122(2) . . ? C14C C19C H19C 119.0 . . ? C18C C19C H19C 118.9 . . ? C43C C41C C42C 112(3) . . ? C43C C41C C4C 106(2) . . ? C42C C41C C4C 113(2) . . ? C43C C41C C44C 101(3) . . ? C42C C41C C44C 112(3) . . ? C4C C41C C44C 112(2) . . ? C41C C42C H42G 109.5 . . ? C41C C42C H42H 109.4 . . ? H42G C42C H42H 109.5 . . ? C41C C42C H42I 109.5 . . ? H42G C42C H42I 109.5 . . ? H42H C42C H42I 109.5 . . ? C41C C43C H43G 109.4 . . ? C41C C43C H43H 109.5 . . ? H43G C43C H43H 109.5 . . ? C41C C43C H43I 109.5 . . ? H43G C43C H43I 109.5 . . ? H43H C43C H43I 109.5 . . ? C41C C44C H44G 109.4 . . ? C41C C44C H44H 109.5 . . ? H44G C44C H44H 109.5 . . ? C41C C44C H44I 109.5 . . ? H44G C44C H44I 109.5 . . ? H44H C44C H44I 109.5 . . ? 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 C11A O1A C1A C2A -129(2) . . . . ? C11A O1A C1A C6A 45(3) . . . . ? C6A C1A C2A C3A -1(4) . . . . ? O1A C1A C2A C3A 172(2) . . . . ? C6A C1A C2A C9C 178(2) . . . . ? O1A C1A C2A C9C -9(3) . . . . ? C1A C2A C3A C4A 8(4) . . . . ? C9C C2A C3A C4A -172(2) . . . . ? C2A C3A C4A C5A -7(4) . . . . ? C2A C3A C4A C41A 178(2) . . . . ? C3A C4A C5A C6A 1(4) . . . . ? C41A C4A C5A C6A 176(2) . . . . ? C2A C1A C6A C5A -5(4) . . . . ? O1A C1A C6A C5A -178(2) . . . . ? C2A C1A C6A C7A -170(3) . . . . ? O1A C1A C6A C7A 17(4) . . . . ? C4A C5A C6A C1A 4(4) . . . . ? C4A C5A C6A C7A 171(3) . . . . ? C1A C6A C7A O8A 54(4) . . . . ? C5A C6A C7A O8A -111(2) . . . . ? C6A C7A O8A C9A 46(3) . . . . ? C7A O8A C9A C2B 171.2(18) . . . . ? C1A O1A C11A C12A 136(2) . . . . ? O1A C11A C12A O12A -169(3) . . . . ? O1A C11A C12A N13A -5(4) . . . . ? O12A C12A N13A C14A -20(6) . . . . ? C11A C12A N13A C14A 179(2) . . . . ? C12A N13A C14A C19A -15(5) . . . . ? C12A N13A C14A C15A 155(3) . . . . ? C19A C14A C15A C16A -10(4) . . . . ? N13A C14A C15A C16A 179(2) . . . . ? C14A C15A C16A C17A 10(4) . . . . ? C15A C16A C17A C18A -13(6) . . . . ? C15A C16A C17A F17A 178(2) . . . . ? C16A C17A C18A C19A 12(7) . . . . ? F17A C17A C18A C19A 180(3) . . . . ? C15A C14A C19A C18A 9(5) . . . . ? N13A C14A C19A C18A 179(3) . . . . ? C17A C18A C19A C14A -9(5) . . . . ? C3A C4A C41A C42A 92(4) . . . . ? C5A C4A C41A C42A -83(4) . . . . ? C3A C4A C41A C43A -158(4) . . . . ? C5A C4A C41A C43A 28(5) . . . . ? C3A C4A C41A C44A -22(5) . . . . ? C5A C4A C41A C44A 163(4) . . . . ? C11B O1B C1B C2B -90(3) . . . . ? C11B O1B C1B C6B 98(2) . . . . ? C6B C1B C2B C3B -4(4) . . . . ? O1B C1B C2B C3B -176(2) . . . . ? C6B C1B C2B C9A 164(2) . . . . ? O1B C1B C2B C9A -9(4) . . . . ? O8A C9A C2B C1B 81(3) . . . . ? O8A C9A C2B C3B -111(3) . . . . ? C1B C2B C3B C4B -5(4) . . . . ? C9A C2B C3B C4B -172(2) . . . . ? C2B C3B C4B C5B 7(3) . . . . ? C2B C3B C4B C41B -172(2) . . . . ? C3B C4B C5B C6B -2(3) . . . . ? C41B C4B C5B C6B 177(2) . . . . ? C2B C1B C6B C5B 9(4) . . . . ? O1B C1B C6B C5B -177.8(19) . . . . ? C2B C1B C6B C7B -177(2) . . . . ? O1B C1B C6B C7B -4(3) . . . . ? C4B C5B C6B C1B -7(3) . . . . ? C4B C5B C6B C7B 179.3(17) . . . . ? C1B C6B C7B O8B 57(3) . . . . ? C5B C6B C7B O8B -129(2) . . . . ? C6B C7B O8B C9B 60(2) . . . . ? C7B O8B C9B C2C -103(2) . . . . ? C1B O1B C11B C12B -167(2) . . . . ? O1B C11B C12B O12B -175(2) . . . . ? O1B C11B C12B N13B 11(3) . . . . ? O12B C12B N13B C14B 1(4) . . . . ? C11B C12B N13B C14B 174(2) . . . . ? C12B N13B C14B C15B -30(4) . . . . ? C12B N13B C14B C19B 148(3) . . . . ? N13B C14B C15B C16B -175(3) . . . . ? C19B C14B C15B C16B 6(4) . . . . ? C14B C15B C16B C17B -12(5) . . . . ? C15B C16B C17B F17B 174(3) . . . . ? C15B C16B C17B C18B 17(5) . . . . ? F17B C17B C18B C19B -172(3) . . . . ? C16B C17B C18B C19B -17(5) . . . . ? C17B C18B C19B C14B 11(5) . . . . ? N13B C14B C19B C18B 176(3) . . . . ? C15B C14B C19B C18B -6(4) . . . . ? C5B C4B C41B C42B -19(4) . . . . ? C3B C4B C41B C42B 160(3) . . . . ? C5B C4B C41B C44B -143(3) . . . . ? C3B C4B C41B C44B 36(4) . . . . ? C5B C4B C41B C43B 94(4) . . . . ? C3B C4B C41B C43B -87(4) . . . . ? C11C O1C C1C C6C 96(2) . . . . ? C11C O1C C1C C2C -84(2) . . . . ? O8B C9B C2C C1C -52(3) . . . . ? O8B C9B C2C C3C 123(2) . . . . ? C6C C1C C2C C9B 180(2) . . . . ? O1C C1C C2C C9B -1(3) . . . . ? C6C C1C C2C C3C 4(3) . . . . ? O1C C1C C2C C3C -176.5(18) . . . . ? C9B C2C C3C C4C -179(2) . . . . ? C1C C2C C3C C4C -3(3) . . . . ? C2C C3C C4C C5C 3(3) . . . . ? C2C C3C C4C C41C -179(2) . . . . ? C3C C4C C5C C6C -1(3) . . . . ? C41C C4C C5C C6C -180(2) . . . . ? C2C C1C C6C C5C -3(3) . . . . ? O1C C1C C6C C5C 177.4(19) . . . . ? C2C C1C C6C C7C 178(2) . . . . ? O1C C1C C6C C7C -2(3) . . . . ? C4C C5C C6C C1C 1(3) . . . . ? C4C C5C C6C C7C -179(2) . . . . ? C1C C6C C7C O8C 61(3) . . . . ? C5C C6C C7C O8C -118(2) . . . . ? C6C C7C O8C C9C 136(2) . . . . ? C7C O8C C9C C2A -82(2) . . . . ? C1A C2A C9C O8C -66(3) . . . . ? C3A C2A C9C O8C 113(2) . . . . ? C1C O1C C11C C12C 157.7(18) . . . . ? O1C C11C C12C O12C 156(2) . . . . ? O1C C11C C12C N13C -37(3) . . . . ? O12C C12C N13C C14C -27(4) . . . . ? C11C C12C N13C C14C 166(2) . . . . ? C12C N13C C14C C15C 13(4) . . . . ? C12C N13C C14C C19C -175(3) . . . . ? C19C C14C C15C C16C 10(5) . . . . ? N13C C14C C15C C16C -179(3) . . . . ? C14C C15C C16C C17C -10(6) . . . . ? C15C C16C C17C C18C 9(6) . . . . ? C15C C16C C17C F17C 177(3) . . . . ? F17C C17C C18C C19C -175(3) . . . . ? C16C C17C C18C C19C -7(6) . . . . ? C15C C14C C19C C18C -8(5) . . . . ? N13C C14C C19C C18C -179(3) . . . . ? C17C C18C C19C C14C 6(5) . . . . ? C5C C4C C41C C43C -57(4) . . . . ? C3C C4C C41C C43C 125(3) . . . . ? C5C C4C C41C C42C 66(4) . . . . ? C3C C4C C41C C42C -112(3) . . . . ? C5C C4C C41C C44C -166(3) . . . . ? C3C C4C C41C C44C 15(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N13A H13A O1A 0.86 2.21 2.70(3) 116.1 . N13B H13B O1B 0.86 2.24 2.68(2) 112.2 . N13B H13B O1C 0.86 2.46 3.26(3) 154.1 . N13C H13C O8B 0.86 2.30 3.16(2) 175.9 . N13C H13C O1C 0.86 2.40 2.70(2) 100.5 . _diffrn_measured_fraction_theta_max 0.793 _diffrn_reflns_theta_full 20.00 _diffrn_measured_fraction_theta_full 0.793 _refine_diff_density_max 0.806 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.170