# 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 'Lee, Dongwhan' _publ_contact_author_email dongwhan@indiana.edu _publ_section_title ; The art of stacking: structural folding and self-assembly of branched p-conjugation assisted by O-H***O and C-H***F hydrogen bonds ; loop_ _publ_author_name D.Lee H.Lee A.Olasz M.Pink H.Park # Attachment '- CCDC783201_1F_rev.cif' data_10041new_noCHCl3 _database_code_depnum_ccdc_archive 'CCDC 783201' #TrackingRef '- CCDC783201_1F_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C51 H45 F3 O3, 2(C1 H1 Cl3) ' _chemical_formula_sum 'C51 H45 F3 O3' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colourless _diffrn_ambient_temperature 150(2) _chemical_formula_weight 762.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4830(8) _cell_length_b 14.9544(12) _cell_length_c 15.7398(13) _cell_angle_alpha 89.095(2) _cell_angle_beta 86.983(2) _cell_angle_gamma 71.805(2) _cell_volume 2340.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2046 _cell_measurement_theta_min 1.93 _cell_measurement_theta_max 24.71 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.082 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9890 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details 'SADABS (R. Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'APEX II Kappa Duo' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type kappa _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 29791 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 24.71 _reflns_number_total 7914 _reflns_number_gt 5124 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II (2009)' _computing_cell_refinement 'Bruker APEX II (2009)' _computing_data_reduction 'Bruker APEX II (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.2d (2010)' _computing_publication_material 'WinGX (2005)' _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. One t-butyl group was found to be disordered with large thermal parameters. The bond lengths C32-C33, C32-C34 and C32-C35 were constrained with SADI and DFIX commands. The thermal parameters of C33, C34 and C35 were restrained with SIMU command. ; _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^)+(0.1110P)^2^+1.2063P] 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 7914 _refine_ls_number_parameters 523 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1035 _refine_ls_R_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.2237 _refine_ls_wR_factor_gt 0.2059 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.093 _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 F1 F 0.9047(2) 0.42481(14) 0.50032(15) 0.0656(7) Uani 1 1 d . . . F2 F 0.5177(2) 0.67808(15) 0.45914(16) 0.0664(6) Uani 1 1 d . . . F3 F 0.8752(3) 0.60946(17) 0.25672(19) 0.0845(8) Uani 1 1 d . . . O1 O 1.1187(2) 0.12367(18) 0.54569(17) 0.0573(7) Uani 1 1 d . . . H1 H 1.0543 0.1379 0.5132 0.086 Uiso 1 1 calc R . . O2 O 0.1027(3) 0.83516(19) 0.5429(2) 0.0676(8) Uani 1 1 d . . . H2 H 0.1364 0.8652 0.5749 0.101 Uiso 1 1 calc R . . O3 O 0.2551(2) 0.94641(18) 0.58049(14) 0.0486(6) Uani 1 1 d . . . H3 H 0.2139 1.0031 0.5704 0.073 Uiso 1 1 calc R . . C1 C 0.8949(3) 0.5150(2) 0.3767(2) 0.0434(9) Uani 1 1 d . . . C2 C 0.8353(3) 0.4970(2) 0.4535(2) 0.0401(8) Uani 1 1 d . . . C3 C 0.7078(3) 0.5492(2) 0.4835(2) 0.0376(8) Uani 1 1 d . . . C4 C 0.6398(3) 0.6246(2) 0.4326(2) 0.0403(8) Uani 1 1 d . . . C5 C 0.6920(3) 0.6473(2) 0.3563(2) 0.0411(8) Uani 1 1 d . . . C6 C 0.8198(3) 0.5910(2) 0.3307(2) 0.0443(8) Uani 1 1 d . . . C7 C 1.0227(3) 0.4569(2) 0.3452(2) 0.0422(8) Uani 1 1 d . . . C8 C 1.1287(3) 0.4076(2) 0.3163(2) 0.0408(8) Uani 1 1 d . . . C9 C 0.6442(4) 0.5285(2) 0.5608(3) 0.0432(9) Uani 1 1 d . . . C10 C 0.5801(4) 0.5176(2) 0.6230(2) 0.0452(9) Uani 1 1 d . . . C11 C 0.6171(3) 0.7258(2) 0.3073(2) 0.0422(8) Uani 1 1 d . . . C12 C 0.5486(3) 0.7926(2) 0.2705(2) 0.0392(8) Uani 1 1 d . . . C13 C 1.2539(3) 0.3488(2) 0.2790(2) 0.0355(8) Uani 1 1 d . . . C14 C 1.3056(3) 0.3751(2) 0.2032(2) 0.0431(9) Uani 1 1 d . . . H14 H 1.2579 0.4326 0.1769 0.052 Uiso 1 1 calc R . . C15 C 1.4255(4) 0.3190(2) 0.1650(2) 0.0432(8) Uani 1 1 d . . . H15 H 1.4594 0.3392 0.1136 0.052 Uiso 1 1 calc R . . C16 C 1.4970(3) 0.2336(2) 0.20081(18) 0.0338(7) Uani 1 1 d . . . C17 C 1.4444(3) 0.2081(2) 0.27711(19) 0.0332(7) Uani 1 1 d . . . H17 H 1.4917 0.1502 0.3030 0.040 Uiso 1 1 calc R . . C18 C 1.3258(3) 0.2637(2) 0.31653(18) 0.0309(7) Uani 1 1 d . . . C19 C 1.6289(3) 0.1687(2) 0.16093(19) 0.0358(7) Uani 1 1 d . . . C20 C 1.7411(4) 0.1613(3) 0.2207(2) 0.0509(9) Uani 1 1 d . . . H20A H 1.7476 0.2242 0.2309 0.076 Uiso 1 1 calc R . . H20B H 1.8265 0.1212 0.1949 0.076 Uiso 1 1 calc R . . H20C H 1.7215 0.1338 0.2748 0.076 Uiso 1 1 calc R . . C21 C 1.6171(4) 0.0702(2) 0.1479(2) 0.0508(9) Uani 1 1 d . . . H21A H 1.6013 0.0434 0.2032 0.076 Uiso 1 1 calc R . . H21B H 1.7007 0.0296 0.1203 0.076 Uiso 1 1 calc R . . H21C H 1.5419 0.0746 0.1119 0.076 Uiso 1 1 calc R . . C22 C 1.6661(4) 0.2045(3) 0.0752(2) 0.0554(10) Uani 1 1 d . . . H22A H 1.6796 0.2658 0.0826 0.083 Uiso 1 1 calc R . . H22B H 1.5935 0.2110 0.0365 0.083 Uiso 1 1 calc R . . H22C H 1.7493 0.1596 0.0512 0.083 Uiso 1 1 calc R . . C23 C 1.2755(3) 0.2360(2) 0.3962(2) 0.0353(8) Uani 1 1 d . . . C24 C 1.2317(3) 0.2162(2) 0.4629(2) 0.0365(8) Uani 1 1 d . . . C25 C 1.1779(4) 0.1971(3) 0.5452(2) 0.0498(9) Uani 1 1 d . . . H25A H 1.2514 0.1804 0.5853 0.060 Uiso 1 1 calc R . . H25B H 1.1095 0.2553 0.5664 0.060 Uiso 1 1 calc R . . C26 C 0.4982(4) 0.5108(2) 0.6958(2) 0.0484(9) Uani 1 1 d . . . C27 C 0.5456(5) 0.4456(3) 0.7608(3) 0.0640(12) Uani 1 1 d . . . H27 H 0.6350 0.4039 0.7566 0.077 Uiso 1 1 calc R . . C28 C 0.4629(6) 0.4419(3) 0.8309(3) 0.0814(17) Uani 1 1 d . . . H28 H 0.4971 0.3968 0.8739 0.098 Uiso 1 1 calc R . . C29 C 0.3332(6) 0.5007(3) 0.8410(3) 0.0767(15) Uani 1 1 d . . . C30 C 0.2856(5) 0.5654(2) 0.7761(2) 0.0570(11) Uani 1 1 d . . . H30 H 0.1960 0.6068 0.7812 0.068 Uiso 1 1 calc R . . C31 C 0.3655(4) 0.5706(2) 0.7047(2) 0.0467(9) Uani 1 1 d . . . C32 C 0.2483(7) 0.4951(3) 0.9206(3) 0.116(2) Uani 1 1 d DU . . C33 C 0.2541(6) 0.3936(3) 0.9399(3) 0.0880(16) Uani 1 1 d DU . . H33A H 0.2296 0.3659 0.8897 0.132 Uiso 1 1 calc R . . H33B H 0.1911 0.3926 0.9878 0.132 Uiso 1 1 calc R . . H33C H 0.3455 0.3572 0.9545 0.132 Uiso 1 1 calc R . . C34 C 0.3111(13) 0.5275(5) 0.9979(3) 0.224(5) Uani 1 1 d DU . . H34A H 0.3305 0.5861 0.9835 0.335 Uiso 1 1 calc R . . H34B H 0.3946 0.4786 1.0113 0.335 Uiso 1 1 calc R . . H34C H 0.2475 0.5381 1.0474 0.335 Uiso 1 1 calc R . . C35 C 0.1022(8) 0.5524(5) 0.9097(5) 0.221(5) Uani 1 1 d DU . . H35A H 0.0649 0.5233 0.8660 0.331 Uiso 1 1 calc R . . H35B H 0.0969 0.6167 0.8924 0.331 Uiso 1 1 calc R . . H35C H 0.0506 0.5543 0.9638 0.331 Uiso 1 1 calc R . . C36 C 0.3102(4) 0.6368(2) 0.6389(2) 0.0435(8) Uani 1 1 d . . . C37 C 0.2628(4) 0.6903(2) 0.5837(2) 0.0438(8) Uani 1 1 d . . . C38 C 0.2031(4) 0.7526(3) 0.5138(3) 0.0569(10) Uani 1 1 d . . . H38A H 0.2746 0.7704 0.4809 0.068 Uiso 1 1 calc R . . H38B H 0.1632 0.7183 0.4751 0.068 Uiso 1 1 calc R . . C39 C 0.4615(3) 0.8729(2) 0.2296(2) 0.0341(7) Uani 1 1 d . . . C40 C 0.3744(3) 0.9458(2) 0.27974(19) 0.0307(7) Uani 1 1 d . . . C41 C 0.2851(3) 1.0233(2) 0.24001(19) 0.0318(7) Uani 1 1 d . . . H41 H 0.2278 1.0731 0.2741 0.038 Uiso 1 1 calc R . . C42 C 0.2785(3) 1.0289(2) 0.15271(19) 0.0323(7) Uani 1 1 d . . . C43 C 0.3670(3) 0.9560(2) 0.1045(2) 0.0378(8) Uani 1 1 d . . . H43 H 0.3657 0.9591 0.0442 0.045 Uiso 1 1 calc R . . C44 C 0.4561(3) 0.8798(2) 0.1419(2) 0.0403(8) Uani 1 1 d . . . H44 H 0.5147 0.8312 0.1072 0.048 Uiso 1 1 calc R . . C45 C 0.1770(3) 1.1103(2) 0.1081(2) 0.0413(8) Uani 1 1 d . . . C46 C 0.0843(3) 1.0699(2) 0.0594(2) 0.0445(8) Uani 1 1 d . . . H46A H 0.1373 1.0268 0.0151 0.067 Uiso 1 1 calc R . . H46B H 0.0153 1.1214 0.0332 0.067 Uiso 1 1 calc R . . H46C H 0.0410 1.0356 0.0990 0.067 Uiso 1 1 calc R . . C47 C 0.0910(4) 1.1837(2) 0.1715(3) 0.0649(13) Uani 1 1 d . . . H47A H 0.1486 1.2125 0.2008 0.097 Uiso 1 1 calc R . . H47B H 0.0456 1.1532 0.2133 0.097 Uiso 1 1 calc R . . H47C H 0.0238 1.2324 0.1411 0.097 Uiso 1 1 calc R . . C48 C 0.2510(5) 1.1578(3) 0.0449(3) 0.0709(13) Uani 1 1 d . . . H48A H 0.3083 1.1855 0.0758 0.106 Uiso 1 1 calc R . . H48B H 0.1855 1.2073 0.0143 0.106 Uiso 1 1 calc R . . H48C H 0.3068 1.1109 0.0043 0.106 Uiso 1 1 calc R . . C49 C 0.3772(3) 0.9401(2) 0.3702(2) 0.0350(7) Uani 1 1 d . . . C50 C 0.3804(3) 0.9314(2) 0.4462(2) 0.0380(8) Uani 1 1 d . . . C51 C 0.3849(3) 0.9208(3) 0.5380(2) 0.0461(9) Uani 1 1 d . . . H51A H 0.4337 0.8545 0.5516 0.055 Uiso 1 1 calc R . . H51B H 0.4360 0.9604 0.5599 0.055 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 F1 0.0691(15) 0.0417(12) 0.0815(16) 0.0041(11) -0.0357(13) -0.0058(11) F2 0.0571(14) 0.0522(13) 0.0827(16) 0.0053(11) -0.0059(12) -0.0064(11) F3 0.0676(16) 0.0573(15) 0.113(2) 0.0227(14) 0.0048(15) 0.0010(13) O1 0.0433(14) 0.0614(17) 0.0693(17) 0.0160(13) -0.0102(13) -0.0192(13) O2 0.0528(16) 0.0541(17) 0.099(2) 0.0236(15) -0.0314(15) -0.0180(14) O3 0.0527(15) 0.0553(15) 0.0369(13) 0.0055(11) -0.0018(11) -0.0159(12) C1 0.0347(18) 0.0240(16) 0.071(3) 0.0004(16) -0.0176(17) -0.0059(14) C2 0.0407(19) 0.0208(15) 0.058(2) 0.0042(14) -0.0263(17) -0.0044(14) C3 0.0412(19) 0.0242(15) 0.049(2) 0.0002(14) -0.0159(16) -0.0097(15) C4 0.0285(17) 0.0253(16) 0.061(2) 0.0002(15) -0.0099(16) 0.0019(14) C5 0.0313(17) 0.0237(16) 0.065(2) 0.0061(15) -0.0111(16) -0.0020(14) C6 0.041(2) 0.0311(17) 0.060(2) 0.0093(16) 0.0011(17) -0.0123(16) C7 0.0343(19) 0.0261(16) 0.064(2) 0.0006(15) -0.0161(17) -0.0035(16) C8 0.039(2) 0.0257(16) 0.059(2) 0.0032(15) -0.0190(17) -0.0097(16) C9 0.049(2) 0.0266(17) 0.054(2) -0.0010(16) -0.0249(19) -0.0074(16) C10 0.059(2) 0.0329(18) 0.046(2) 0.0033(16) -0.022(2) -0.0148(17) C11 0.0382(19) 0.0299(17) 0.054(2) 0.0045(15) -0.0018(16) -0.0035(15) C12 0.0383(18) 0.0279(16) 0.0461(19) 0.0020(14) -0.0009(15) -0.0032(15) C13 0.0328(17) 0.0258(15) 0.0472(19) -0.0040(14) -0.0131(15) -0.0061(14) C14 0.045(2) 0.0270(16) 0.056(2) 0.0108(15) -0.0196(17) -0.0068(16) C15 0.053(2) 0.0380(18) 0.0423(19) 0.0119(15) -0.0129(17) -0.0183(17) C16 0.0451(19) 0.0315(16) 0.0272(16) 0.0009(12) -0.0049(14) -0.0151(15) C17 0.0363(17) 0.0264(15) 0.0332(17) -0.0006(13) -0.0093(14) -0.0034(14) C18 0.0331(17) 0.0286(15) 0.0297(16) -0.0027(12) -0.0092(13) -0.0066(14) C19 0.0432(19) 0.0359(17) 0.0281(16) -0.0002(13) 0.0017(14) -0.0127(15) C20 0.044(2) 0.058(2) 0.044(2) -0.0078(17) 0.0004(17) -0.0068(18) C21 0.056(2) 0.0394(19) 0.055(2) -0.0129(17) 0.0172(18) -0.0142(18) C22 0.069(3) 0.055(2) 0.043(2) 0.0066(17) 0.0038(19) -0.023(2) C23 0.0269(16) 0.0308(16) 0.042(2) -0.0084(14) -0.0107(15) 0.0015(14) C24 0.0265(16) 0.0389(18) 0.039(2) -0.0061(15) -0.0019(15) -0.0024(14) C25 0.045(2) 0.055(2) 0.046(2) -0.0051(17) 0.0000(17) -0.0109(18) C26 0.075(3) 0.0329(18) 0.041(2) 0.0068(15) -0.0218(19) -0.0203(19) C27 0.098(3) 0.040(2) 0.052(3) 0.0124(18) -0.033(2) -0.015(2) C28 0.161(5) 0.038(2) 0.038(2) 0.0152(18) -0.020(3) -0.019(3) C29 0.148(5) 0.029(2) 0.045(2) 0.0085(17) 0.005(3) -0.019(3) C30 0.095(3) 0.0313(18) 0.046(2) 0.0065(16) 0.003(2) -0.022(2) C31 0.079(3) 0.0283(17) 0.0388(19) 0.0074(14) -0.0176(19) -0.0231(19) C32 0.237(7) 0.037(2) 0.052(3) 0.014(2) 0.045(4) -0.021(3) C33 0.134(5) 0.048(2) 0.074(3) 0.024(2) 0.006(3) -0.020(3) C34 0.563(16) 0.109(5) 0.050(3) -0.012(3) 0.048(6) -0.189(8) C35 0.253(7) 0.106(5) 0.180(7) 0.107(5) 0.164(6) 0.089(5) C36 0.061(2) 0.0339(17) 0.0411(19) 0.0045(15) -0.0061(17) -0.0223(17) C37 0.053(2) 0.0379(18) 0.049(2) 0.0097(16) -0.0137(17) -0.0250(17) C38 0.067(3) 0.048(2) 0.064(2) 0.0220(19) -0.027(2) -0.028(2) C39 0.0334(17) 0.0247(15) 0.0406(18) 0.0053(13) -0.0006(14) -0.0043(14) C40 0.0305(16) 0.0267(15) 0.0330(16) 0.0027(12) -0.0016(13) -0.0065(13) C41 0.0302(16) 0.0248(15) 0.0375(17) -0.0026(12) -0.0030(13) -0.0042(13) C42 0.0353(17) 0.0242(15) 0.0398(18) 0.0041(13) -0.0083(14) -0.0120(13) C43 0.0439(19) 0.0369(18) 0.0299(16) 0.0022(13) -0.0006(14) -0.0092(16) C44 0.0403(19) 0.0306(16) 0.0419(19) -0.0025(14) 0.0023(15) 0.0000(15) C45 0.046(2) 0.0286(16) 0.049(2) 0.0095(14) -0.0168(16) -0.0088(15) C46 0.045(2) 0.0443(19) 0.044(2) 0.0037(15) -0.0131(16) -0.0121(16) C47 0.069(3) 0.0293(18) 0.081(3) -0.0059(18) -0.045(2) 0.0127(18) C48 0.076(3) 0.058(2) 0.092(3) 0.045(2) -0.040(3) -0.036(2) C49 0.0318(17) 0.0295(16) 0.0399(19) 0.0007(13) -0.0041(14) -0.0036(14) C50 0.0331(17) 0.0428(18) 0.0378(19) 0.0032(14) -0.0045(14) -0.0113(15) C51 0.042(2) 0.057(2) 0.0391(19) 0.0072(16) -0.0075(16) -0.0132(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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.6988 (0.0107) x + 11.5494 (0.0127) y + 8.0307 (0.0184) z = 14.9722 (0.0031) * -0.0033 (0.0022) C1 * 0.0059 (0.0022) C2 * -0.0050 (0.0021) C3 * 0.0017 (0.0023) C4 * 0.0008 (0.0023) C5 * 0.0000 (0.0024) C6 Rms deviation of fitted atoms = 0.0035 7.5322 (0.0088) x + 10.0636 (0.0143) y + 8.6166 (0.0168) z = 15.3621 (0.0087) Angle to previous plane (with approximate esd) = 8.98 ( 0.19 ) * -0.0037 (0.0021) C13 * -0.0027 (0.0022) C14 * 0.0072 (0.0022) C15 * -0.0052 (0.0021) C16 * -0.0012 (0.0021) C17 * 0.0056 (0.0020) C18 Rms deviation of fitted atoms = 0.0047 6.6988 (0.0107) x + 11.5494 (0.0127) y + 8.0307 (0.0184) z = 14.9722 (0.0031) Angle to previous plane (with approximate esd) = 8.98 ( 0.19 ) * -0.0033 (0.0022) C1 * 0.0059 (0.0022) C2 * -0.0050 (0.0021) C3 * 0.0017 (0.0023) C4 * 0.0008 (0.0023) C5 * 0.0000 (0.0024) C6 Rms deviation of fitted atoms = 0.0035 6.0854 (0.0137) x + 12.2190 (0.0141) y + 7.7632 (0.0223) z = 14.6714 (0.0095) Angle to previous plane (with approximate esd) = 5.13 ( 0.22 ) * 0.0037 (0.0025) C26 * 0.0005 (0.0028) C27 * -0.0044 (0.0032) C28 * 0.0041 (0.0031) C29 * 0.0001 (0.0027) C30 * -0.0040 (0.0024) C31 Rms deviation of fitted atoms = 0.0033 6.6988 (0.0107) x + 11.5494 (0.0127) y + 8.0307 (0.0184) z = 14.9722 (0.0031) Angle to previous plane (with approximate esd) = 5.13 ( 0.22 ) * -0.0033 (0.0022) C1 * 0.0059 (0.0022) C2 * -0.0050 (0.0021) C3 * 0.0017 (0.0023) C4 * 0.0008 (0.0023) C5 * 0.0000 (0.0024) C6 Rms deviation of fitted atoms = 0.0035 9.2102 (0.0065) x + 10.8718 (0.0134) y + 0.2118 (0.0209) z = 13.7927 (0.0117) Angle to previous plane (with approximate esd) = 33.57 ( 0.12 ) * -0.0034 (0.0022) C39 * -0.0026 (0.0022) C40 * 0.0089 (0.0022) C41 * -0.0091 (0.0022) C42 * 0.0032 (0.0024) C43 * 0.0030 (0.0024) C44 Rms deviation of fitted atoms = 0.0058 Torsion angles O O O O O1 O3 O2 O1 -13.3(2) O3 O2 O1 O3 14.7(2) O2 O1 O3 O2 -12.0(2) Intermolecular C ... F distance F1 C38 3.207(5) Intramolecular C ... F distance F2 C38 3.209(5) ; 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 F1 C2 1.334(4) . ? F2 C4 1.329(4) . ? F3 C6 1.337(4) . ? O1 C25 1.420(4) . ? O1 H1 0.8400 . ? O2 C38 1.413(5) . ? O2 H2 0.8400 . ? O3 C51 1.425(4) . ? O3 H3 0.8400 . ? C1 C6 1.382(5) . ? C1 C2 1.392(5) . ? C1 C7 1.419(5) . ? C2 C3 1.382(5) . ? C3 C4 1.398(4) . ? C3 C9 1.433(6) . ? C4 C5 1.376(5) . ? C5 C6 1.384(5) . ? C5 C11 1.432(4) . ? C7 C8 1.196(5) . ? C8 C13 1.434(5) . ? C9 C10 1.195(5) . ? C10 C26 1.418(6) . ? C11 C12 1.193(4) . ? C12 C39 1.430(4) . ? C13 C14 1.387(5) . ? C13 C18 1.400(4) . ? C14 C15 1.387(5) . ? C14 H14 0.9500 . ? C15 C16 1.390(4) . ? C15 H15 0.9500 . ? C16 C17 1.393(4) . ? C16 C19 1.530(4) . ? C17 C18 1.382(4) . ? C17 H17 0.9500 . ? C18 C23 1.440(5) . ? C19 C20 1.520(5) . ? C19 C22 1.520(5) . ? C19 C21 1.535(5) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.193(5) . ? C24 C25 1.446(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C31 1.401(5) . ? C26 C27 1.401(5) . ? C27 C28 1.378(7) . ? C27 H27 0.9500 . ? C28 C29 1.372(7) . ? C28 H28 0.9500 . ? C29 C30 1.396(5) . ? C29 C32 1.514(7) . ? C30 C31 1.382(5) . ? C30 H30 0.9500 . ? C31 C36 1.435(5) . ? C32 C35 1.520(8) . ? C32 C33 1.526(5) . ? C32 C34 1.566(8) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C37 1.191(5) . ? C37 C38 1.465(5) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C44 1.385(4) . ? C39 C40 1.405(4) . ? C40 C41 1.404(4) . ? C40 C49 1.427(4) . ? C41 C42 1.379(4) . ? C41 H41 0.9500 . ? C42 C43 1.395(4) . ? C42 C45 1.533(4) . ? C43 C44 1.375(4) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 C48 1.528(5) . ? C45 C47 1.529(5) . ? C45 C46 1.535(5) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 C50 1.202(4) . ? C50 C51 1.453(5) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? 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 C25 O1 H1 109.5 . . ? C38 O2 H2 109.5 . . ? C51 O3 H3 109.5 . . ? C6 C1 C2 116.1(3) . . ? C6 C1 C7 121.4(4) . . ? C2 C1 C7 122.4(3) . . ? F1 C2 C3 118.2(3) . . ? F1 C2 C1 118.1(3) . . ? C3 C2 C1 123.7(3) . . ? C2 C3 C4 116.0(3) . . ? C2 C3 C9 123.8(3) . . ? C4 C3 C9 120.2(3) . . ? F2 C4 C5 117.7(3) . . ? F2 C4 C3 118.5(3) . . ? C5 C4 C3 123.8(3) . . ? C4 C5 C6 116.4(3) . . ? C4 C5 C11 121.0(3) . . ? C6 C5 C11 122.6(3) . . ? F3 C6 C1 117.0(3) . . ? F3 C6 C5 119.0(3) . . ? C1 C6 C5 124.0(3) . . ? C8 C7 C1 178.0(4) . . ? C7 C8 C13 178.1(4) . . ? C10 C9 C3 173.7(3) . . ? C9 C10 C26 176.2(4) . . ? C12 C11 C5 175.9(4) . . ? C11 C12 C39 177.3(4) . . ? C14 C13 C18 118.4(3) . . ? C14 C13 C8 119.9(3) . . ? C18 C13 C8 121.7(3) . . ? C15 C14 C13 121.2(3) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 121.1(3) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C15 C16 C17 117.2(3) . . ? C15 C16 C19 123.2(3) . . ? C17 C16 C19 119.6(3) . . ? C18 C17 C16 122.4(3) . . ? C18 C17 H17 118.8 . . ? C16 C17 H17 118.8 . . ? C17 C18 C13 119.7(3) . . ? C17 C18 C23 121.1(3) . . ? C13 C18 C23 119.2(3) . . ? C20 C19 C22 108.7(3) . . ? C20 C19 C16 109.0(2) . . ? C22 C19 C16 112.4(3) . . ? C20 C19 C21 108.8(3) . . ? C22 C19 C21 108.1(3) . . ? C16 C19 C21 109.8(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C18 177.8(3) . . ? C23 C24 C25 177.0(3) . . ? O1 C25 C24 114.7(3) . . ? O1 C25 H25A 108.6 . . ? C24 C25 H25A 108.6 . . ? O1 C25 H25B 108.6 . . ? C24 C25 H25B 108.6 . . ? H25A C25 H25B 107.6 . . ? C31 C26 C27 117.9(4) . . ? C31 C26 C10 120.0(3) . . ? C27 C26 C10 122.1(4) . . ? C28 C27 C26 120.2(4) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C29 C28 C27 122.6(4) . . ? C29 C28 H28 118.7 . . ? C27 C28 H28 118.7 . . ? C28 C29 C30 117.2(4) . . ? C28 C29 C32 120.3(4) . . ? C30 C29 C32 122.5(5) . . ? C31 C30 C29 121.7(4) . . ? C31 C30 H30 119.2 . . ? C29 C30 H30 119.2 . . ? C30 C31 C26 120.4(3) . . ? C30 C31 C36 119.3(4) . . ? C26 C31 C36 120.3(3) . . ? C29 C32 C35 110.4(4) . . ? C29 C32 C33 111.1(4) . . ? C35 C32 C33 108.1(5) . . ? C29 C32 C34 108.2(5) . . ? C35 C32 C34 113.4(7) . . ? C33 C32 C34 105.5(4) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C37 C36 C31 178.4(4) . . ? C36 C37 C38 177.5(4) . . ? O2 C38 C37 112.4(3) . . ? O2 C38 H38A 109.1 . . ? C37 C38 H38A 109.1 . . ? O2 C38 H38B 109.1 . . ? C37 C38 H38B 109.1 . . ? H38A C38 H38B 107.9 . . ? C44 C39 C40 118.6(3) . . ? C44 C39 C12 122.2(3) . . ? C40 C39 C12 119.1(3) . . ? C41 C40 C39 119.4(3) . . ? C41 C40 C49 120.8(3) . . ? C39 C40 C49 119.7(3) . . ? C42 C41 C40 121.6(3) . . ? C42 C41 H41 119.2 . . ? C40 C41 H41 119.2 . . ? C41 C42 C43 117.7(3) . . ? C41 C42 C45 122.6(3) . . ? C43 C42 C45 119.7(3) . . ? C44 C43 C42 121.7(3) . . ? C44 C43 H43 119.1 . . ? C42 C43 H43 119.1 . . ? C43 C44 C39 120.9(3) . . ? C43 C44 H44 119.6 . . ? C39 C44 H44 119.6 . . ? C48 C45 C47 109.1(3) . . ? C48 C45 C42 109.8(3) . . ? C47 C45 C42 111.8(3) . . ? C48 C45 C46 109.0(3) . . ? C47 C45 C46 108.7(3) . . ? C42 C45 C46 108.3(3) . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C45 C47 H47A 109.5 . . ? C45 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C45 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C45 C48 H48A 109.5 . . ? C45 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C45 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C50 C49 C40 177.4(3) . . ? C49 C50 C51 179.7(3) . . ? O3 C51 C50 113.3(3) . . ? O3 C51 H51A 108.9 . . ? C50 C51 H51A 108.9 . . ? O3 C51 H51B 108.9 . . ? C50 C51 H51B 108.9 . . ? H51A C51 H51B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F1 -179.5(3) . . . . ? C7 C1 C2 F1 3.2(5) . . . . ? C6 C1 C2 C3 1.1(5) . . . . ? C7 C1 C2 C3 -176.1(3) . . . . ? F1 C2 C3 C4 179.4(3) . . . . ? C1 C2 C3 C4 -1.3(5) . . . . ? F1 C2 C3 C9 -1.9(5) . . . . ? C1 C2 C3 C9 177.4(3) . . . . ? C2 C3 C4 F2 -178.9(3) . . . . ? C9 C3 C4 F2 2.4(5) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? C9 C3 C4 C5 -177.9(3) . . . . ? F2 C4 C5 C6 179.4(3) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? F2 C4 C5 C11 -0.1(5) . . . . ? C3 C4 C5 C11 -179.8(3) . . . . ? C2 C1 C6 F3 180.0(3) . . . . ? C7 C1 C6 F3 -2.7(5) . . . . ? C2 C1 C6 C5 -0.5(5) . . . . ? C7 C1 C6 C5 176.8(3) . . . . ? C4 C5 C6 F3 179.6(3) . . . . ? C11 C5 C6 F3 -0.9(5) . . . . ? C4 C5 C6 C1 0.2(5) . . . . ? C11 C5 C6 C1 179.6(3) . . . . ? C6 C1 C7 C8 -50(11) . . . . ? C2 C1 C7 C8 127(11) . . . . ? C1 C7 C8 C13 7(20) . . . . ? C2 C3 C9 C10 -171(3) . . . . ? C4 C3 C9 C10 7(3) . . . . ? C3 C9 C10 C26 -22(8) . . . . ? C4 C5 C11 C12 5(5) . . . . ? C6 C5 C11 C12 -174(5) . . . . ? C5 C11 C12 C39 -10(12) . . . . ? C7 C8 C13 C14 49(11) . . . . ? C7 C8 C13 C18 -130(10) . . . . ? C18 C13 C14 C15 0.0(5) . . . . ? C8 C13 C14 C15 -179.2(3) . . . . ? C13 C14 C15 C16 1.1(5) . . . . ? C14 C15 C16 C17 -1.2(5) . . . . ? C14 C15 C16 C19 179.4(3) . . . . ? C15 C16 C17 C18 0.4(4) . . . . ? C19 C16 C17 C18 179.8(3) . . . . ? C16 C17 C18 C13 0.6(4) . . . . ? C16 C17 C18 C23 -178.9(3) . . . . ? C14 C13 C18 C17 -0.8(4) . . . . ? C8 C13 C18 C17 178.4(3) . . . . ? C14 C13 C18 C23 178.7(3) . . . . ? C8 C13 C18 C23 -2.2(4) . . . . ? C15 C16 C19 C20 116.0(3) . . . . ? C17 C16 C19 C20 -63.3(4) . . . . ? C15 C16 C19 C22 -4.6(4) . . . . ? C17 C16 C19 C22 176.1(3) . . . . ? C15 C16 C19 C21 -124.9(3) . . . . ? C17 C16 C19 C21 55.8(4) . . . . ? C17 C18 C23 C24 152(8) . . . . ? C13 C18 C23 C24 -28(9) . . . . ? C18 C23 C24 C25 -22(13) . . . . ? C23 C24 C25 O1 157(6) . . . . ? C9 C10 C26 C31 19(6) . . . . ? C9 C10 C26 C27 -161(5) . . . . ? C31 C26 C27 C28 -0.3(5) . . . . ? C10 C26 C27 C28 179.4(4) . . . . ? C26 C27 C28 C29 -0.5(7) . . . . ? C27 C28 C29 C30 0.8(7) . . . . ? C27 C28 C29 C32 -178.3(4) . . . . ? C28 C29 C30 C31 -0.4(6) . . . . ? C32 C29 C30 C31 178.8(4) . . . . ? C29 C30 C31 C26 -0.4(6) . . . . ? C29 C30 C31 C36 178.4(4) . . . . ? C27 C26 C31 C30 0.7(5) . . . . ? C10 C26 C31 C30 -179.0(3) . . . . ? C27 C26 C31 C36 -178.1(3) . . . . ? C10 C26 C31 C36 2.2(5) . . . . ? C28 C29 C32 C35 -168.8(6) . . . . ? C30 C29 C32 C35 12.1(7) . . . . ? C28 C29 C32 C33 -48.8(7) . . . . ? C30 C29 C32 C33 132.1(5) . . . . ? C28 C29 C32 C34 66.6(6) . . . . ? C30 C29 C32 C34 -112.6(6) . . . . ? C30 C31 C36 C37 -78(16) . . . . ? C26 C31 C36 C37 101(16) . . . . ? C31 C36 C37 C38 -17(23) . . . . ? C36 C37 C38 O2 127(10) . . . . ? C11 C12 C39 C44 -141(8) . . . . ? C11 C12 C39 C40 37(8) . . . . ? C44 C39 C40 C41 -0.2(5) . . . . ? C12 C39 C40 C41 -177.7(3) . . . . ? C44 C39 C40 C49 179.5(3) . . . . ? C12 C39 C40 C49 2.0(5) . . . . ? C39 C40 C41 C42 1.4(5) . . . . ? C49 C40 C41 C42 -178.3(3) . . . . ? C40 C41 C42 C43 -2.0(5) . . . . ? C40 C41 C42 C45 176.8(3) . . . . ? C41 C42 C43 C44 1.4(5) . . . . ? C45 C42 C43 C44 -177.4(3) . . . . ? C42 C43 C44 C39 -0.3(5) . . . . ? C40 C39 C44 C43 -0.3(5) . . . . ? C12 C39 C44 C43 177.1(3) . . . . ? C41 C42 C45 C48 123.5(4) . . . . ? C43 C42 C45 C48 -57.7(4) . . . . ? C41 C42 C45 C47 2.2(5) . . . . ? C43 C42 C45 C47 -179.0(3) . . . . ? C41 C42 C45 C46 -117.5(3) . . . . ? C43 C42 C45 C46 61.2(4) . . . . ? C41 C40 C49 C50 142(7) . . . . ? C39 C40 C49 C50 -38(7) . . . . ? C40 C49 C50 C51 85(77) . . . . ? C49 C50 C51 O3 176(100) . . . . ? 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 O1 H1 O2 0.84 1.84 2.670(4) 170.6 2_666 O2 H2 O3 0.84 2.00 2.731(4) 145.5 . O3 H3 O1 0.84 1.81 2.654(4) 177.0 1_465 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.479 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.054 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.044 0.202 0.011 236 58 ' ' 2 0.043 0.798 -0.011 236 58 ' ' 3 0.436 0.707 0.510 246 59 ' ' 4 0.563 0.293 0.490 246 59 ' ' _platon_squeeze_details ; The Squeeze command from Platon suggested 235 electron counts per cell which corresponds to approximately four CHCl3 molecules in the unit cell (2 CHCl3 per formula unit). These solvents molecules have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. However, they were included in D(calc), F000 and Mol. Weight. ; # start Validation Reply Form _vrf_FORMU01_10041new_noCHCl3 ; PROBLEM: Discrepancy in _chemical_formula_sum and _chemical_formula_moiety. RESPONSE: The contribution of the diffuse contributing solvent (= 2 chloroform molecules) to the structure factors was assessed by back-Fourier transformation, and the data were corrected accordingly using Platon/SQUEEZE. The sum formula excludes the 2 chloroform molecules. As a consequence, the formula and all other formula-dependent values are incorrect. Values derived for a formula including 2 chloroforms are as follows: _chemical_formula_sum 'C53 H47 Cl6 F3 O3' _chemical_formula_weight 1001.61 _exptl_crystal_density_diffrn 1.421 _exptl_crystal_F_000 1036 _exptl_absorpt_coefficient_mu 0.424 ; # Attachment '- CCDC783202_1U.cif' data_08112 _database_code_depnum_ccdc_archive 'CCDC 783202' #TrackingRef '- CCDC783202_1U.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C51 H45 F3 O3, 2.27 (C H Cl3)' _chemical_formula_sum 'C53.27 H47.27 Cl6.82 F3 O3' _chemical_formula_weight 1034.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 17.1496(12) _cell_length_b 17.1496 _cell_length_c 33.798(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8608.5(9) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9976 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3204 _exptl_absorpt_coefficient_mu 0.385 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9445 _exptl_absorpt_correction_T_max 0.9698 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details '0.30 degree frames measured for 60 seconds each' _diffrn_measurement_method 'omega and phi scans' _diffrn_measurement_device 'APEX Kappa Duo' _diffrn_measurement_device_type Kappa _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker APEXII' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 26759 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0152 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 25.07 _reflns_number_total 3403 _reflns_number_gt 2596 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II v.2.2 (Bruker, 2007)' _computing_cell_refinement 'APEX II v.2.2 (Bruker, 2007)' _computing_data_reduction 'APEX II v.2.2 (Bruker, 2007)' _computing_structure_solution 'SIR-2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker, 2008)' _computing_publication_material 'SHELXTL (Bruker, 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^ > 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. Residue O1,C5>c10,C15>c17 is disordered over two sites, for which 1,2 and 1,3 distances were restrained to be the same length with an effective standard deviation. A FLAT instruction was also included for the phenyl ring. Further the thermal displacement parameters of atoms within 0.5 angstrom were constrained to be the same (EADP). The t-butyl group is disordered over three sites; DELU and SAME instructions were applied. The two disorders seem to be correlated (investigating a free refinement of site occupancies) and were therefore treated as such. Solvent (CHCl3) is disordered over three sites and was refined with a strong set of restraints and constraints (DELU, SAME and a common thermal displacement parameter). ; _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^)+(0.1733P)^2^+16.9529P] 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 3403 _refine_ls_number_parameters 276 _refine_ls_number_restraints 784 _refine_ls_R_factor_all 0.1089 _refine_ls_R_factor_gt 0.0905 _refine_ls_wR_factor_ref 0.2960 _refine_ls_wR_factor_gt 0.2683 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.116 _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 F1 F 0.82817(11) 0.96438(12) 0.11356(5) 0.0545(6) Uani 1 1 d U . . C1 C 0.91337(19) 0.9824(2) 0.11382(7) 0.0456(7) Uani 1 1 d U . . C2 C 0.92866(19) 0.90979(19) 0.11374(7) 0.0465(7) Uani 1 1 d U . . C3 C 0.8564(2) 0.8191(2) 0.11201(8) 0.0499(7) Uani 1 1 d U A . C4 C 0.7949(2) 0.7433(2) 0.10957(8) 0.0503(7) Uani 1 1 d U . . C5 C 0.7211(2) 0.6547(2) 0.10382(8) 0.0491(7) Uani 0.718(3) 1 d PDU A 1 C6 C 0.6841(4) 0.6281(4) 0.06570(15) 0.0511(14) Uani 0.718(3) 1 d PDU A 1 C7 C 0.6121(5) 0.5427(4) 0.0598(2) 0.0592(17) Uani 0.718(3) 1 d PDU A 1 H7 H 0.5872 0.5257 0.0340 0.071 Uiso 0.718(3) 1 calc PR A 1 C8 C 0.5749(6) 0.4810(5) 0.0904(3) 0.0654(9) Uani 0.718(3) 1 d PDU A 1 C9 C 0.6119(4) 0.5093(5) 0.1280(2) 0.0618(17) Uani 0.718(3) 1 d PDU A 1 H9 H 0.5867 0.4689 0.1496 0.074 Uiso 0.718(3) 1 calc PR A 1 C10 C 0.6832(4) 0.5935(4) 0.1347(2) 0.0561(15) Uani 0.718(3) 1 d PDU A 1 H10 H 0.7071 0.6103 0.1607 0.067 Uiso 0.718(3) 1 calc PR A 1 C11 C 0.4963(6) 0.3864(5) 0.0844(3) 0.0901(13) Uani 0.523(7) 1 d PDU A 1 C12 C 0.5224(8) 0.3195(6) 0.1026(4) 0.110(3) Uani 0.523(7) 1 d PDU A 1 H12A H 0.4728 0.2577 0.0988 0.166 Uiso 0.523(7) 1 calc PR A 1 H12B H 0.5343 0.3317 0.1309 0.166 Uiso 0.523(7) 1 calc PR A 1 H12C H 0.5765 0.3266 0.0894 0.166 Uiso 0.523(7) 1 calc PR A 1 C13 C 0.4683(9) 0.3607(8) 0.0412(3) 0.108(3) Uani 0.523(7) 1 d PDU A 1 H13A H 0.4173 0.2990 0.0399 0.162 Uiso 0.523(7) 1 calc PR A 1 H13B H 0.5190 0.3646 0.0262 0.162 Uiso 0.523(7) 1 calc PR A 1 H13C H 0.4505 0.4021 0.0297 0.162 Uiso 0.523(7) 1 calc PR A 1 C14 C 0.4149(8) 0.3742(7) 0.1088(3) 0.115(3) Uani 0.523(7) 1 d PDU A 1 H14A H 0.3634 0.3139 0.1040 0.172 Uiso 0.523(7) 1 calc PR A 1 H14B H 0.3993 0.4197 0.1008 0.172 Uiso 0.523(7) 1 calc PR A 1 H14C H 0.4302 0.3811 0.1370 0.172 Uiso 0.523(7) 1 calc PR A 1 C15 C 0.7195(4) 0.6902(3) 0.03312(13) 0.0598(12) Uani 0.718(3) 1 d PDU A 1 C16 C 0.7442(4) 0.7409(3) 0.00583(13) 0.0681(12) Uani 0.718(3) 1 d PDU A 1 C17 C 0.7756(4) 0.8030(4) -0.02816(15) 0.0857(16) Uani 0.718(3) 1 d PDU A 1 H17A H 0.7742 0.7696 -0.0523 0.103 Uiso 0.718(3) 1 calc PR A 1 H17B H 0.7342 0.8268 -0.0323 0.103 Uiso 0.718(3) 1 calc PR A 1 O1 O 0.8648(3) 0.8764(2) -0.02230(10) 0.0723(11) Uani 0.718(3) 1 d PDU A 1 H1O H 0.8984 0.8565 -0.0151 0.087 Uiso 0.718(3) 1 calc PR A 1 C11E C 0.4963(6) 0.3864(5) 0.0844(3) 0.0901(13) Uani 0.195(7) 1 d PU B 3 C12E C 0.5072(19) 0.3451(16) 0.0455(6) 0.115(3) Uani 0.195(7) 1 d PDU B 3 H12D H 0.5282 0.3905 0.0245 0.172 Uiso 0.195(7) 1 calc PR B 3 H12E H 0.4490 0.2934 0.0380 0.172 Uiso 0.195(7) 1 calc PR B 3 H12F H 0.5512 0.3252 0.0495 0.172 Uiso 0.195(7) 1 calc PR B 3 C13E C 0.4134(14) 0.3980(15) 0.0792(8) 0.110(3) Uani 0.195(7) 1 d PDU B 3 H13D H 0.4228 0.4374 0.0565 0.166 Uiso 0.195(7) 1 calc PR B 3 H13E H 0.4048 0.4250 0.1032 0.166 Uiso 0.195(7) 1 calc PR B 3 H13F H 0.3599 0.3391 0.0746 0.166 Uiso 0.195(7) 1 calc PR B 3 C14E C 0.475(2) 0.3176(15) 0.1165(6) 0.108(3) Uani 0.195(7) 1 d PDU B 3 H14D H 0.5297 0.3161 0.1235 0.162 Uiso 0.195(7) 1 calc PR B 3 H14E H 0.4291 0.2581 0.1070 0.162 Uiso 0.195(7) 1 calc PR B 3 H14F H 0.4524 0.3338 0.1399 0.162 Uiso 0.195(7) 1 calc PR B 3 C5D C 0.7211(2) 0.6547(2) 0.10382(8) 0.0491(7) Uani 0.282(3) 1 d PDU A 2 C6D C 0.6967(11) 0.6174(11) 0.0657(4) 0.0511(14) Uani 0.282(3) 1 d PDU A 2 C7D C 0.6253(13) 0.5322(12) 0.0600(6) 0.0592(17) Uani 0.282(3) 1 d PDU A 2 H7D H 0.6118 0.5081 0.0339 0.071 Uiso 0.282(3) 1 calc PR A 2 C8D C 0.5725(14) 0.4807(12) 0.0911(7) 0.0654(9) Uani 0.282(3) 1 d PDU A 2 C9D C 0.5944(13) 0.5171(13) 0.1289(7) 0.0618(17) Uani 0.282(3) 1 d PDU A 2 H9D H 0.5591 0.4833 0.1509 0.074 Uiso 0.282(3) 1 calc PR A 2 C10D C 0.6662(12) 0.6011(12) 0.1347(5) 0.0561(15) Uani 0.282(3) 1 d PDU A 2 H10D H 0.6796 0.6242 0.1608 0.067 Uiso 0.282(3) 1 calc PR A 2 C11D C 0.4981(13) 0.3858(13) 0.0825(6) 0.0901(13) Uani 0.282(3) 1 d PDU A 2 C12D C 0.5428(13) 0.3276(11) 0.0795(7) 0.110(3) Uani 0.282(3) 1 d PDU A 2 H12G H 0.4964 0.2643 0.0764 0.166 Uiso 0.282(3) 1 calc PR A 2 H12H H 0.5774 0.3347 0.1037 0.166 Uiso 0.282(3) 1 calc PR A 2 H12I H 0.5833 0.3468 0.0566 0.166 Uiso 0.282(3) 1 calc PR A 2 C13D C 0.4444(16) 0.3835(15) 0.0455(6) 0.108(3) Uani 0.282(3) 1 d PDU A 2 H13G H 0.4007 0.3209 0.0388 0.162 Uiso 0.282(3) 1 calc PR A 2 H13H H 0.4858 0.4118 0.0233 0.162 Uiso 0.282(3) 1 calc PR A 2 H13I H 0.4124 0.4164 0.0509 0.162 Uiso 0.282(3) 1 calc PR A 2 C14D C 0.4275(15) 0.3437(15) 0.1146(6) 0.115(3) Uani 0.282(3) 1 d PDU A 2 H14G H 0.3901 0.2789 0.1098 0.172 Uiso 0.282(3) 1 calc PR A 2 H14H H 0.3896 0.3716 0.1145 0.172 Uiso 0.282(3) 1 calc PR A 2 H14I H 0.4572 0.3535 0.1404 0.172 Uiso 0.282(3) 1 calc PR A 2 C15D C 0.7498(9) 0.6680(9) 0.0324(3) 0.0598(12) Uani 0.282(3) 1 d PDU A 2 C16D C 0.7924(9) 0.7089(8) 0.0048(3) 0.0681(12) Uani 0.282(3) 1 d PDU A 2 C17D C 0.8438(11) 0.7586(9) -0.0305(3) 0.0857(16) Uani 0.282(3) 1 d PDU A 2 H17C H 0.8797 0.7318 -0.0400 0.103 Uiso 0.282(3) 1 calc PR A 2 H17D H 0.8012 0.7521 -0.0517 0.103 Uiso 0.282(3) 1 calc PR A 2 O1D O 0.9024(7) 0.8515(6) -0.0229(3) 0.0723(11) Uani 0.282(3) 1 d PDU A 2 H1DO H 0.9268 0.8579 -0.0007 0.087 Uiso 0.282(3) 1 calc PR A 2 Cl1 Cl 0.5977(6) 0.7941(6) 0.1307(3) 0.1697(16) Uiso 0.369(5) 1 d PDU C 1 Cl2 Cl 0.5752(6) 0.8173(6) 0.0452(2) 0.1697(16) Uiso 0.369(5) 1 d PDU C 1 Cl3 Cl 0.4783(5) 0.6491(5) 0.0794(3) 0.1697(16) Uiso 0.369(5) 1 d PDU C 1 C1S C 0.5687(15) 0.7552(10) 0.0849(4) 0.1697(16) Uiso 0.369(5) 1 d PDU C 1 H1S H 0.6186 0.7430 0.0785 0.204 Uiso 0.369(5) 1 calc PR C 1 Cl1D Cl 0.6266(11) 0.8180(10) 0.1009(5) 0.1697(16) Uiso 0.157(3) 1 d PD D 2 Cl2D Cl 0.5068(13) 0.7774(12) 0.0374(5) 0.1697(16) Uiso 0.157(3) 1 d PD D 2 Cl3D Cl 0.4931(12) 0.6542(11) 0.1037(6) 0.1697(16) Uiso 0.157(3) 1 d PD D 2 C1SD C 0.551(2) 0.7386(16) 0.0712(9) 0.1697(16) Uiso 0.157(3) 1 d PD D 2 H1SD H 0.5865 0.7180 0.0553 0.204 Uiso 0.157(3) 1 calc PR D 2 Cl1E Cl 0.5851(13) 0.8178(12) 0.1286(6) 0.1697(16) Uiso 0.158(3) 1 d PD E 3 Cl2E Cl 0.4298(11) 0.6457(10) 0.1215(5) 0.1697(16) Uiso 0.158(3) 1 d PD E 3 Cl3E Cl 0.5356(12) 0.7318(11) 0.0563(5) 0.1697(16) Uiso 0.158(3) 1 d PD E 3 C1SE C 0.5365(17) 0.7164(16) 0.1061(6) 0.1697(16) Uiso 0.158(3) 1 d PD E 3 H1E H 0.5737 0.6876 0.1116 0.204 Uiso 0.158(3) 1 calc PR E 3 Cl1F Cl 0.538(3) 0.730(3) 0.1276(8) 0.1697(16) Uiso 0.074(4) 1 d PD F 4 Cl2F Cl 0.601(2) 0.825(2) 0.0543(11) 0.1697(16) Uiso 0.074(4) 1 d PD F 4 Cl3F Cl 0.440(2) 0.655(2) 0.0594(10) 0.1697(16) Uiso 0.074(4) 1 d PD F 4 C1F C 0.512(3) 0.753(2) 0.0823(9) 0.1697(16) Uiso 0.074(4) 1 d PD F 4 H1SF H 0.4770 0.7838 0.0872 0.204 Uiso 0.074(4) 1 calc PR F 4 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 F1 0.0530(10) 0.0691(11) 0.0429(10) 0.0046(7) 0.0049(7) 0.0316(9) C1 0.0519(16) 0.0605(17) 0.0252(13) 0.0022(11) 0.0023(10) 0.0286(13) C2 0.0575(16) 0.0540(16) 0.0263(13) 0.0008(10) 0.0014(11) 0.0266(13) C3 0.0597(17) 0.0571(17) 0.0322(14) 0.0035(11) 0.0025(11) 0.0286(15) C4 0.0621(17) 0.0575(17) 0.0357(14) 0.0024(12) 0.0024(12) 0.0331(15) C5 0.0609(15) 0.0516(14) 0.0393(14) 0.0025(11) 0.0008(11) 0.0315(12) C6 0.062(2) 0.055(2) 0.0375(14) 0.0058(13) 0.0016(13) 0.0297(16) C7 0.069(3) 0.061(2) 0.0407(15) 0.0040(16) -0.0045(17) 0.0269(19) C8 0.0744(18) 0.0587(16) 0.0490(16) 0.0089(13) -0.0077(13) 0.0228(14) C9 0.074(3) 0.057(2) 0.0456(17) 0.0126(15) -0.005(2) 0.025(2) C10 0.071(3) 0.0552(19) 0.0404(15) 0.0045(14) -0.0066(18) 0.0308(18) C11 0.094(2) 0.0671(19) 0.068(2) 0.0122(16) -0.0151(17) 0.0088(17) C12 0.117(4) 0.063(3) 0.096(5) 0.004(4) -0.012(4) 0.004(3) C13 0.106(5) 0.079(4) 0.078(4) 0.004(3) -0.023(4) 0.000(4) C14 0.103(4) 0.081(5) 0.087(4) 0.024(4) -0.008(3) -0.010(4) C15 0.067(2) 0.062(2) 0.0367(16) 0.0031(16) -0.0010(18) 0.0219(17) C16 0.077(3) 0.064(2) 0.0412(19) 0.0040(17) -0.0012(18) 0.0184(18) C17 0.094(3) 0.073(3) 0.044(2) 0.011(2) -0.002(2) 0.007(2) O1 0.074(2) 0.070(2) 0.0554(17) 0.0176(14) 0.0078(16) 0.0235(16) C11E 0.094(2) 0.0671(19) 0.068(2) 0.0122(16) -0.0151(17) 0.0088(17) C12E 0.103(4) 0.081(5) 0.087(4) 0.024(4) -0.008(3) -0.010(4) C13E 0.117(4) 0.063(3) 0.096(5) 0.004(4) -0.012(4) 0.004(3) C14E 0.106(5) 0.079(4) 0.078(4) 0.004(3) -0.023(4) 0.000(4) C5D 0.0609(15) 0.0516(14) 0.0393(14) 0.0025(11) 0.0008(11) 0.0315(12) C6D 0.062(2) 0.055(2) 0.0375(14) 0.0058(13) 0.0016(13) 0.0297(16) C7D 0.069(3) 0.061(2) 0.0407(15) 0.0040(16) -0.0045(17) 0.0269(19) C8D 0.0744(18) 0.0587(16) 0.0490(16) 0.0089(13) -0.0077(13) 0.0228(14) C9D 0.074(3) 0.057(2) 0.0456(17) 0.0126(15) -0.005(2) 0.025(2) C10D 0.071(3) 0.0552(19) 0.0404(15) 0.0045(14) -0.0066(18) 0.0308(18) C11D 0.094(2) 0.0671(19) 0.068(2) 0.0122(16) -0.0151(17) 0.0088(17) C12D 0.117(4) 0.063(3) 0.096(5) 0.004(4) -0.012(4) 0.004(3) C13D 0.106(5) 0.079(4) 0.078(4) 0.004(3) -0.023(4) 0.000(4) C14D 0.103(4) 0.081(5) 0.087(4) 0.024(4) -0.008(3) -0.010(4) C15D 0.067(2) 0.062(2) 0.0367(16) 0.0031(16) -0.0010(18) 0.0219(17) C16D 0.077(3) 0.064(2) 0.0412(19) 0.0040(17) -0.0012(18) 0.0184(18) C17D 0.094(3) 0.073(3) 0.044(2) 0.011(2) -0.002(2) 0.007(2) O1D 0.074(2) 0.070(2) 0.0554(17) 0.0176(14) 0.0078(16) 0.0235(16) _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. Distance C9_a - F1_$5 3.2275 (0.0081) Torsion Angle O1O1O1O1 91.63 ( 0.17) O1_$7a - O1_$8a - O1_$10a Torsion Angle O1DO1DO1DO1D 90.90 ( 0.48) O1D_$7b - O1D_$8b - O1D_$10b Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 15.8520 (0.0232) x - 12.8833 (0.0392) y - 6.2499 (0.1111) z = 2.3434 (0.0408) * 0.0039 (0.0034) C5_a * -0.0003 (0.0035) C6_a * -0.0060 (0.0044) C7_a * 0.0088 (0.0049) C8_a * -0.0054 (0.0044) C9_a * -0.0009 (0.0035) C10_a Rms deviation of fitted atoms = 0.0051 - 0.0000 (0.0000) x - 0.0000 (0.0000) y + 33.7978 (0.0024) z = 3.8456 (0.0018) Angle to previous plane (with approximate esd) = 79.34 ( 0.19 ) * 0.0013 (0.0018) C1 * -0.0013 (0.0018) C2 * 0.0013 (0.0018) C1_$3 * -0.0013 (0.0018) C2_$3 * 0.0013 (0.0018) C1_$4 * -0.0013 (0.0018) C2_$4 Rms deviation of fitted atoms = 0.0013 15.6715 (0.0684) x - 13.6242 (0.0975) y + 3.8605 (0.4162) z = 2.7724 (0.1095) Angle to previous plane (with approximate esd) = 83.44 ( 0.71 ) * 0.0093 (0.0085) C5D_b * -0.0123 (0.0089) C6D_b * 0.0067 (0.0095) C7D_b * 0.0019 (0.0098) C8D_b * -0.0046 (0.0094) C9D_b * -0.0011 (0.0089) C10D_b Rms deviation of fitted atoms = 0.0072 ; 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 F1 C1 1.334(3) . ? C1 C2 1.380(4) 3_675 ? C1 C2 1.395(4) . ? C2 C1 1.380(4) 2_765 ? C2 C3 1.425(4) . ? C3 C4 1.199(4) . ? C4 C5 1.423(4) . ? C5 C10 1.391(6) . ? C5 C6 1.408(6) . ? C6 C7 1.378(7) . ? C6 C15 1.439(6) . ? C7 C8 1.386(7) . ? C7 H7 0.9500 . ? C8 C9 1.396(7) . ? C8 C11 1.517(7) . ? C9 C10 1.365(7) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C13 1.533(10) . ? C11 C14 1.542(12) . ? C11 C12 1.552(12) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.191(6) . ? C16 C17 1.473(6) . ? C17 O1 1.427(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? O1 H1O 0.8400 . ? C12E H12D 0.9800 . ? C12E H12E 0.9800 . ? C12E H12F 0.9800 . ? C13E H13D 0.9800 . ? C13E H13E 0.9800 . ? C13E H13F 0.9800 . ? C14E H14D 0.9800 . ? C14E H14E 0.9800 . ? C14E H14F 0.9800 . ? C6D C7D 1.372(14) . ? C6D C15D 1.435(13) . ? C7D C8D 1.383(15) . ? C7D H7D 0.9500 . ? C8D C9D 1.388(15) . ? C8D C11D 1.512(14) . ? C9D C10D 1.362(15) . ? C9D H9D 0.9500 . ? C10D H10D 0.9500 . ? C11D C14D 1.515(17) . ? C11D C12D 1.534(18) . ? C11D C13D 1.542(16) . ? C12D H12G 0.9800 . ? C12D H12H 0.9800 . ? C12D H12I 0.9800 . ? C13D H13G 0.9800 . ? C13D H13H 0.9800 . ? C13D H13I 0.9800 . ? C14D H14G 0.9800 . ? C14D H14H 0.9800 . ? C14D H14I 0.9800 . ? C15D C16D 1.178(12) . ? C16D C17D 1.473(13) . ? C17D O1D 1.419(13) . ? C17D H17C 0.9900 . ? C17D H17D 0.9900 . ? O1D H1DO 0.8400 . ? Cl1 C1S 1.659(13) . ? Cl2 C1S 1.682(13) . ? Cl3 C1S 1.712(13) . ? C1S H1S 1.0000 . ? Cl1D C1SD 1.667(17) . ? Cl2D C1SD 1.681(16) . ? Cl3D C1SD 1.688(17) . ? C1SD H1SD 1.0000 . ? Cl1E C1SE 1.688(17) . ? Cl2E C1SE 1.695(17) . ? Cl3E C1SE 1.704(16) . ? C1SE H1E 1.0000 . ? Cl1F C1F 1.688(17) . ? Cl2F C1F 1.692(17) . ? Cl3F C1F 1.699(17) . ? C1F H1SF 1.0000 . ? 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 F1 C1 C2 118.4(3) . 3_675 ? F1 C1 C2 117.8(3) . . ? C2 C1 C2 123.8(3) 3_675 . ? C1 C2 C1 116.2(3) 2_765 . ? C1 C2 C3 122.1(3) 2_765 . ? C1 C2 C3 121.7(3) . . ? C4 C3 C2 178.2(3) . . ? C3 C4 C5 175.9(3) . . ? C10 C5 C6 118.5(4) . . ? C10 C5 C4 122.3(4) . . ? C6 C5 C4 119.2(3) . . ? C7 C6 C5 119.8(5) . . ? C7 C6 C15 119.9(5) . . ? C5 C6 C15 120.3(5) . . ? C6 C7 C8 122.0(6) . . ? C6 C7 H7 119.0 . . ? C8 C7 H7 119.0 . . ? C7 C8 C9 117.2(6) . . ? C7 C8 C11 122.8(6) . . ? C9 C8 C11 120.0(6) . . ? C10 C9 C8 122.0(6) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C9 C10 C5 120.5(6) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? C8 C11 C13 114.7(7) . . ? C8 C11 C14 109.6(7) . . ? C13 C11 C14 109.7(8) . . ? C8 C11 C12 107.9(7) . . ? C13 C11 C12 109.2(8) . . ? C14 C11 C12 105.3(8) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C6 176.4(6) . . ? C15 C16 C17 179.0(7) . . ? O1 C17 C16 111.9(4) . . ? O1 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? O1 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C17 O1 H1O 109.5 . . ? H12D C12E H12E 109.5 . . ? H12D C12E H12F 109.5 . . ? H12E C12E H12F 109.5 . . ? H13D C13E H13E 109.5 . . ? H13D C13E H13F 109.5 . . ? H13E C13E H13F 109.5 . . ? H14D C14E H14E 109.5 . . ? H14D C14E H14F 109.5 . . ? H14E C14E H14F 109.5 . . ? C7D C6D C15D 119.4(13) . . ? C6D C7D C8D 121.5(16) . . ? C6D C7D H7D 119.2 . . ? C8D C7D H7D 119.2 . . ? C7D C8D C9D 118.0(14) . . ? C7D C8D C11D 118.1(15) . . ? C9D C8D C11D 123.7(15) . . ? C10D C9D C8D 120.3(16) . . ? C10D C9D H9D 119.8 . . ? C8D C9D H9D 119.8 . . ? C9D C10D H10D 118.5 . . ? C8D C11D C14D 114.6(15) . . ? C8D C11D C12D 106.6(15) . . ? C14D C11D C12D 106.2(16) . . ? C8D C11D C13D 110.8(15) . . ? C14D C11D C13D 104.1(16) . . ? C12D C11D C13D 114.7(17) . . ? C11D C12D H12G 109.5 . . ? C11D C12D H12H 109.5 . . ? H12G C12D H12H 109.5 . . ? C11D C12D H12I 109.5 . . ? H12G C12D H12I 109.5 . . ? H12H C12D H12I 109.5 . . ? C11D C13D H13G 109.5 . . ? C11D C13D H13H 109.5 . . ? H13G C13D H13H 109.5 . . ? C11D C13D H13I 109.5 . . ? H13G C13D H13I 109.5 . . ? H13H C13D H13I 109.5 . . ? C11D C14D H14G 109.5 . . ? C11D C14D H14H 109.5 . . ? H14G C14D H14H 109.5 . . ? C11D C14D H14I 109.5 . . ? H14G C14D H14I 109.5 . . ? H14H C14D H14I 109.5 . . ? C16D C15D C6D 179.2(17) . . ? C15D C16D C17D 178.6(15) . . ? O1D C17D C16D 112.8(11) . . ? O1D C17D H17C 109.0 . . ? C16D C17D H17C 109.0 . . ? O1D C17D H17D 109.0 . . ? C16D C17D H17D 109.0 . . ? H17C C17D H17D 107.8 . . ? C17D O1D H1DO 109.5 . . ? Cl1 C1S Cl2 125.3(11) . . ? Cl1 C1S Cl3 117.4(10) . . ? Cl2 C1S Cl3 108.9(9) . . ? Cl1 C1S H1S 99.7 . . ? Cl2 C1S H1S 99.7 . . ? Cl3 C1S H1S 99.7 . . ? Cl1D C1SD Cl2D 114.0(17) . . ? Cl1D C1SD Cl3D 101.0(14) . . ? Cl2D C1SD Cl3D 126(2) . . ? Cl1D C1SD H1SD 104.4 . . ? Cl2D C1SD H1SD 104.4 . . ? Cl3D C1SD H1SD 104.4 . . ? Cl1E C1SE Cl2E 113.5(17) . . ? Cl1E C1SE Cl3E 108.9(17) . . ? Cl2E C1SE Cl3E 108.9(16) . . ? Cl1E C1SE H1E 108.5 . . ? Cl2E C1SE H1E 108.5 . . ? Cl3E C1SE H1E 108.5 . . ? Cl1F C1F Cl2F 116(2) . . ? Cl1F C1F Cl3F 109(2) . . ? Cl2F C1F Cl3F 115(2) . . ? Cl1F C1F H1SF 105.4 . . ? Cl2F C1F H1SF 105.4 . . ? Cl3F C1F H1SF 105.4 . . ? 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 F1 C1 C2 C1 179.70(14) . . . 2_765 ? C2 C1 C2 C1 0.4(5) 3_675 . . 2_765 ? F1 C1 C2 C3 2.2(4) . . . . ? C2 C1 C2 C3 -177.09(18) 3_675 . . . ? C1 C2 C3 C4 -118(11) 2_765 . . . ? C1 C2 C3 C4 60(11) . . . . ? C2 C3 C4 C5 13(15) . . . . ? C3 C4 C5 C10 -174(4) . . . . ? C3 C4 C5 C6 6(5) . . . . ? C10 C5 C6 C7 -0.1(7) . . . . ? C4 C5 C6 C7 -179.3(4) . . . . ? C10 C5 C6 C15 178.1(5) . . . . ? C4 C5 C6 C15 -1.1(7) . . . . ? C5 C6 C7 C8 -0.8(9) . . . . ? C15 C6 C7 C8 -179.1(7) . . . . ? C6 C7 C8 C9 1.6(10) . . . . ? C6 C7 C8 C11 -179.3(8) . . . . ? C7 C8 C9 C10 -1.6(10) . . . . ? C11 C8 C9 C10 179.4(8) . . . . ? C8 C9 C10 C5 0.7(9) . . . . ? C6 C5 C10 C9 0.2(7) . . . . ? C4 C5 C10 C9 179.4(4) . . . . ? C7 C8 C11 C13 6.8(13) . . . . ? C9 C8 C11 C13 -174.1(9) . . . . ? C7 C8 C11 C14 -117.1(9) . . . . ? C9 C8 C11 C14 61.9(11) . . . . ? C7 C8 C11 C12 128.8(10) . . . . ? C9 C8 C11 C12 -52.2(11) . . . . ? C7 C6 C15 C16 56(9) . . . . ? C5 C6 C15 C16 -123(9) . . . . ? C6 C15 C16 C17 -138(35) . . . . ? C15 C16 C17 O1 -78(38) . . . . ? C15D C6D C7D C8D 179.6(19) . . . . ? C6D C7D C8D C9D -1(2) . . . . ? C6D C7D C8D C11D -177(2) . . . . ? C7D C8D C9D C10D 0(2) . . . . ? C11D C8D C9D C10D 176(2) . . . . ? C7D C8D C11D C14D -163.0(19) . . . . ? C9D C8D C11D C14D 21(3) . . . . ? C7D C8D C11D C12D 80(2) . . . . ? C9D C8D C11D C12D -96(2) . . . . ? C7D C8D C11D C13D -46(2) . . . . ? C9D C8D C11D C13D 139(2) . . . . ? C7D C6D C15D C16D 26(100) . . . . ? C6D C15D C16D C17D -3(100) . . . . ? C15D C16D C17D O1D 144(73) . . . . ? 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 O1 H1O O1 0.84 1.94 2.689(5) 147.1 12_655 O1D H1DO O1D 0.84 2.03 2.723(14) 139.6 12_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.454 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.069