#------------------------------------------------------------------------------ #$Date: 2019-06-13 06:02:18 +0300 (Thu, 13 Jun 2019) $ #$Revision: 215912 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/69/7156914.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7156914 loop_ _publ_author_name 'Peng, Peng' 'Huang, Guo Zhi' 'Sun, Yingxin' 'Wang, Xing' 'Wu, Jingjing' 'Wu, Fanhong' _publ_section_title ; Copper-mediated cascade radical cyclization of olefins with naphthalenyl iododifluoromethyl ketones ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB00916G _journal_year 2019 _chemical_formula_sum 'C20 H22 F2 O' _chemical_formula_weight 316.37 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2019-01-05 deposited with the CCDC. 2019-06-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.519(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.0026(6) _cell_length_b 25.7449(14) _cell_length_c 7.0051(4) _cell_measurement_reflns_used 2715 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 52.388 _cell_measurement_theta_min 5.250 _cell_volume 1753.94(17) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_unetI/netI 0.0442 _diffrn_reflns_Laue_measured_fraction_full 0.961 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 8890 _diffrn_reflns_point_group_measured_fraction_full 0.961 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 2.625 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.198 _exptl_crystal_description prismatic _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.201 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.030 _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 265 _refine_ls_number_reflns 3050 _refine_ls_number_restraints 72 _refine_ls_restrained_S_all 1.138 _refine_ls_R_factor_all 0.1057 _refine_ls_R_factor_gt 0.0747 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1138P)^2^+0.4735P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2071 _refine_ls_wR_factor_ref 0.2380 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1951 _reflns_number_total 3050 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob00916g2.cif _cod_data_source_block dd18103 _cod_database_code 7156914 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-4 _shelx_res_file ; TITL dd18103_a.res in P2(1)/c CELL 0.71073 10.0026 25.7449 7.0051 90 103.519 90 ZERR 4 0.0006 0.0014 0.0004 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F O UNIT 80 88 8 4 OMIT 0 2 0 OMIT -3 4 3 OMIT -6 5 3 OMIT -3 12 3 OMIT -3.00 50.00 L.S. 7 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 HTAB C13 O1_$1 EQIV $1 x, -y+3/2, z-1/2 conf htab mpla c1 > c10 wpdb -1 simu 0.004 c15 > c20 simu 0.004 c15' > c20' dfix 1.55 0.02 c14 c15 c15 c16 c16 c17 c17 c18 c18 c19 c19 c20 dfix 1.55 0.02 c14 c15' c15' c16' c16' c17' c17' c18' c18' c19' c19' c20' HTAB C13 O1_$1 TEMP 23 WGHT 0.113800 0.473500 EXTI 0.108800 FVAR 1.90916 F2 3 0.876208 0.617308 1.496077 11.00000 0.11454 0.16198 = 0.12390 0.02009 0.00466 0.05236 F1 3 0.950451 0.695722 1.496026 11.00000 0.06278 0.23124 = 0.11413 -0.00969 0.00118 -0.04189 O1 4 0.767653 0.694745 1.714437 11.00000 0.07822 0.20004 = 0.07404 -0.01897 -0.01120 -0.00244 C1 1 0.400207 0.666914 1.151174 11.00000 0.05209 0.09565 = 0.05723 0.00214 0.00721 -0.00628 C10 1 0.544515 0.665276 1.245557 11.00000 0.05174 0.08921 = 0.05739 0.00383 0.00804 -0.00241 C6 1 0.305826 0.686861 1.255032 11.00000 0.05530 0.09797 = 0.06572 0.00790 0.01237 -0.00440 C9 1 0.584475 0.682835 1.437234 11.00000 0.05775 0.09300 = 0.05559 0.00224 0.00523 -0.00227 C2 1 0.347675 0.650487 0.956059 11.00000 0.06239 0.14387 = 0.06284 -0.00947 0.00577 -0.00692 AFIX 43 H2 2 0.407280 0.636883 0.884973 11.00000 -1.20000 AFIX 0 C8 1 0.488417 0.701949 1.537807 11.00000 0.07377 0.11620 = 0.06039 -0.00905 0.00976 -0.00059 AFIX 43 H8 2 0.518463 0.713402 1.666637 11.00000 -1.20000 AFIX 0 C5 1 0.164828 0.690265 1.158974 11.00000 0.05009 0.13848 = 0.08447 0.01068 0.01488 0.00026 AFIX 43 H5 2 0.102833 0.703797 1.226281 11.00000 -1.20000 AFIX 0 C7 1 0.353253 0.703890 1.449858 11.00000 0.06659 0.11354 = 0.07295 -0.00465 0.02122 0.00607 AFIX 43 H7 2 0.291062 0.716572 1.518531 11.00000 -1.20000 AFIX 0 C13 1 0.789562 0.668772 1.216069 11.00000 0.05559 0.14237 = 0.08330 0.00078 0.01713 -0.00373 AFIX 23 H13A 2 0.855497 0.650776 1.157950 11.00000 -1.20000 H13B 2 0.787803 0.704888 1.176118 11.00000 -1.20000 AFIX 0 C14 1 0.646574 0.645015 1.136617 11.00000 0.05773 0.12494 = 0.06411 -0.00764 0.01096 -0.00187 AFIX 13 H14 2 0.615473 0.657284 1.001040 11.00000 -1.20000 AFIX 0 C11 1 0.729793 0.682600 1.543595 11.00000 0.06576 0.11186 = 0.06137 0.00297 -0.00257 -0.00627 C12 1 0.835912 0.665833 1.432580 11.00000 0.05292 0.12594 = 0.08650 0.00741 -0.00001 -0.00493 C4 1 0.118934 0.674342 0.972694 11.00000 0.05041 0.16953 = 0.08990 0.01465 -0.00020 -0.01111 AFIX 43 H4 2 0.025867 0.676749 0.912436 11.00000 -1.20000 AFIX 0 C3 1 0.210500 0.654227 0.869599 11.00000 0.06679 0.17844 = 0.06796 -0.00866 -0.00324 -0.01588 AFIX 43 H3 2 0.178059 0.643221 0.740616 11.00000 -1.20000 PART 1 AFIX 0 C15 1 0.648431 0.586742 1.126474 10.60000 0.06606 0.11236 = 0.12749 -0.04592 0.03300 -0.00481 AFIX 23 H15A 2 0.555512 0.573342 1.105804 10.60000 -1.20000 H15B 2 0.702261 0.572721 1.249005 10.60000 -1.20000 AFIX 0 C16 1 0.713071 0.569884 0.952488 10.60000 0.11089 0.13112 = 0.14073 -0.04729 0.03898 0.00374 AFIX 23 H16A 2 0.655860 0.581688 0.828590 10.60000 -1.20000 H16B 2 0.803784 0.585044 0.968303 10.60000 -1.20000 AFIX 0 C17 1 0.722850 0.510633 0.954612 10.60000 0.15359 0.15063 = 0.16620 -0.05745 0.03726 0.01326 AFIX 23 H17A 2 0.630667 0.496788 0.909498 10.60000 -1.20000 H17B 2 0.756549 0.499556 1.089667 10.60000 -1.20000 AFIX 0 C18 1 0.818407 0.484739 0.825687 10.50000 0.18445 0.16449 = 0.18414 -0.05390 0.02693 0.02092 AFIX 23 H18A 2 0.894777 0.507014 0.816101 10.50000 -1.20000 H18B 2 0.852723 0.450962 0.875799 10.50000 -1.20000 AFIX 0 C19 1 0.713009 0.480676 0.632923 10.50000 0.20586 0.17953 = 0.19208 -0.04739 0.02768 0.02209 AFIX 23 H19A 2 0.685855 0.514002 0.571399 10.50000 -1.20000 H19B 2 0.633026 0.460203 0.640606 10.50000 -1.20000 AFIX 0 C20 1 0.828003 0.448075 0.533347 10.50000 0.22854 0.19651 = 0.17902 -0.05376 0.06549 0.04017 AFIX 137 H20A 2 0.919564 0.458923 0.596044 10.50000 -1.50000 H20B 2 0.810454 0.455457 0.395387 10.50000 -1.50000 H20C 2 0.818938 0.411431 0.552373 10.50000 -1.50000 PART 2 AFIX 0 C15' 1 0.646321 0.584841 1.142488 10.40000 0.23519 0.18647 = 0.16848 -0.06748 0.01589 0.06386 AFIX 23 H15C 2 0.661688 0.575274 1.279840 10.40000 -1.20000 H15D 2 0.553241 0.574147 1.080925 10.40000 -1.20000 AFIX 0 C16' 1 0.741496 0.550272 1.055227 10.40000 0.24420 0.19233 = 0.17171 -0.06589 0.01558 0.06140 AFIX 23 H16C 2 0.824510 0.569247 1.050874 10.40000 -1.20000 H16D 2 0.767510 0.519912 1.137529 10.40000 -1.20000 AFIX 0 C17' 1 0.671132 0.533928 0.855532 10.40000 0.25623 0.19750 = 0.17104 -0.05994 0.01438 0.05841 AFIX 23 H17C 2 0.630685 0.564298 0.782343 10.40000 -1.20000 H17D 2 0.596723 0.510579 0.864447 10.40000 -1.20000 AFIX 0 C18' 1 0.767702 0.505682 0.736091 10.50000 0.27189 0.20208 = 0.17802 -0.05627 0.00689 0.05393 AFIX 23 H18C 2 0.744245 0.521626 0.607100 10.50000 -1.20000 H18D 2 0.859621 0.517811 0.796800 10.50000 -1.20000 AFIX 0 C19' 1 0.785175 0.450420 0.697387 10.50000 0.27996 0.20913 = 0.18891 -0.04727 0.00507 0.05238 AFIX 23 H19C 2 0.763733 0.428620 0.799175 10.50000 -1.20000 H19D 2 0.877647 0.442878 0.684395 10.50000 -1.20000 AFIX 0 C20' 1 0.678054 0.443866 0.499446 10.50000 0.29488 0.20607 = 0.20358 -0.04520 -0.00437 0.03323 AFIX 137 H20D 2 0.603447 0.467691 0.494170 10.50000 -1.50000 H20E 2 0.643514 0.408935 0.488605 10.50000 -1.50000 H20F 2 0.720884 0.450915 0.393020 10.50000 -1.50000 PART 0 AFIX 0 HKLF 4 REM dd18103_a.res in P2(1)/c REM R1 = 0.0747 for 1951 Fo > 4sig(Fo) and 0.1057 for all 3050 data REM 265 parameters refined using 72 restraints END WGHT 0.1124 0.4766 REM Instructions for potential hydrogen bonds HTAB C13 O1_$1 REM Highest difference peak 0.201, deepest hole -0.203, 1-sigma level 0.030 Q1 1 0.8311 0.4921 0.6841 11.00000 0.05 0.20 Q2 1 0.7121 0.4770 0.7926 11.00000 0.05 0.16 Q3 1 0.6635 0.4997 0.6957 11.00000 0.05 0.14 Q4 1 0.5737 0.6709 1.3667 11.00000 0.05 0.13 Q5 1 0.6948 0.5220 0.8653 11.00000 0.05 0.13 Q6 1 0.7902 0.5065 1.0358 11.00000 0.05 0.13 Q7 1 0.7530 0.5711 0.9849 11.00000 0.05 0.12 Q8 1 0.4078 0.6218 0.8975 11.00000 0.05 0.11 Q9 1 0.6421 0.5694 0.9046 11.00000 0.05 0.11 Q10 1 0.3848 0.6509 1.0592 11.00000 0.05 0.11 Q11 1 0.9530 0.6560 1.4350 11.00000 0.05 0.10 Q12 1 0.3291 0.6774 1.3643 11.00000 0.05 0.10 Q13 1 0.6251 0.6392 0.9939 11.00000 0.05 0.10 Q14 1 0.7606 0.4449 0.4591 11.00000 0.05 0.10 Q15 1 0.6219 0.4902 0.5490 11.00000 0.05 0.09 Q16 1 0.1771 0.6649 0.6955 11.00000 0.05 0.09 Q17 1 0.4224 0.6564 0.8734 11.00000 0.05 0.09 Q18 1 0.6530 0.5015 1.0767 11.00000 0.05 0.08 Q19 1 0.7369 0.5384 1.1327 11.00000 0.05 0.08 Q20 1 0.7867 0.6531 1.6797 11.00000 0.05 0.08 ; _shelx_res_checksum 77181 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F2 F 0.8762(2) 0.61731(10) 1.4961(3) 0.1373(9) Uani 1 1 d . . . . . F1 F 0.95045(18) 0.69572(11) 1.4960(3) 0.1393(10) Uani 1 1 d . . . . . O1 O 0.7677(2) 0.69474(12) 1.7144(3) 0.1222(10) Uani 1 1 d . . . . . C1 C 0.4002(2) 0.66691(11) 1.1512(3) 0.0692(7) Uani 1 1 d . . . . . C10 C 0.5445(2) 0.66528(10) 1.2456(3) 0.0669(7) Uani 1 1 d . . . . . C6 C 0.3058(2) 0.68686(11) 1.2550(4) 0.0733(8) Uani 1 1 d . . . . . C9 C 0.5845(2) 0.68283(11) 1.4372(3) 0.0701(7) Uani 1 1 d . . . . . C2 C 0.3477(3) 0.65049(14) 0.9561(4) 0.0912(10) Uani 1 1 d . . . . . H2 H 0.4073 0.6369 0.8850 0.109 Uiso 1 1 calc R U . . . C8 C 0.4884(3) 0.70195(12) 1.5378(4) 0.0844(9) Uani 1 1 d . . . . . H8 H 0.5185 0.7134 1.6666 0.101 Uiso 1 1 calc R U . . . C5 C 0.1648(3) 0.69026(14) 1.1590(5) 0.0912(10) Uani 1 1 d . . . . . H5 H 0.1028 0.7038 1.2263 0.109 Uiso 1 1 calc R U . . . C7 C 0.3533(3) 0.70389(12) 1.4499(4) 0.0836(9) Uani 1 1 d . . . . . H7 H 0.2911 0.7166 1.5185 0.100 Uiso 1 1 calc R U . . . C13 C 0.7896(3) 0.66877(15) 1.2161(4) 0.0936(10) Uani 1 1 d . . . . . H13A H 0.8555 0.6508 1.1579 0.112 Uiso 1 1 calc R U . . . H13B H 0.7878 0.7049 1.1761 0.112 Uiso 1 1 calc R U . . . C14 C 0.6466(2) 0.64501(13) 1.1366(4) 0.0828(9) Uani 1 1 d D . . . . H14 H 0.6155 0.6573 1.0010 0.099 Uiso 1 1 calc R U . A 1 C11 C 0.7298(3) 0.68260(12) 1.5436(4) 0.0825(9) Uani 1 1 d . . . . . C12 C 0.8359(3) 0.66583(14) 1.4326(5) 0.0911(10) Uani 1 1 d . . . . . C4 C 0.1189(3) 0.67434(16) 0.9727(5) 0.1060(12) Uani 1 1 d . . . . . H4 H 0.0259 0.6767 0.9124 0.127 Uiso 1 1 calc R U . . . C3 C 0.2105(3) 0.65423(17) 0.8696(5) 0.1075(12) Uani 1 1 d . . . . . H3 H 0.1781 0.6432 0.7406 0.129 Uiso 1 1 calc R U . . . C15 C 0.6484(8) 0.5867(3) 1.1265(19) 0.1003(17) Uani 0.6 1 d D U P B 1 H15A H 0.5555 0.5733 1.1058 0.120 Uiso 0.6 1 calc R U P B 1 H15B H 0.7023 0.5727 1.2490 0.120 Uiso 0.6 1 calc R U P B 1 C16 C 0.7131(8) 0.5699(3) 0.9525(13) 0.1260(17) Uani 0.6 1 d D U P B 1 H16A H 0.6559 0.5817 0.8286 0.151 Uiso 0.6 1 calc R U P B 1 H16B H 0.8038 0.5850 0.9683 0.151 Uiso 0.6 1 calc R U P B 1 C17 C 0.7229(10) 0.5106(3) 0.9546(16) 0.157(2) Uani 0.6 1 d D U P B 1 H17A H 0.6307 0.4968 0.9095 0.188 Uiso 0.6 1 calc R U P B 1 H17B H 0.7565 0.4996 1.0897 0.188 Uiso 0.6 1 calc R U P B 1 C18 C 0.8184(13) 0.4847(6) 0.8257(17) 0.180(3) Uani 0.5 1 d D U P B 1 H18A H 0.8948 0.5070 0.8161 0.216 Uiso 0.5 1 calc R U P B 1 H18B H 0.8527 0.4510 0.8758 0.216 Uiso 0.5 1 calc R U P B 1 C19 C 0.7130(13) 0.4807(7) 0.6329(19) 0.196(3) Uani 0.5 1 d D U P B 1 H19A H 0.6859 0.5140 0.5714 0.235 Uiso 0.5 1 calc R U P B 1 H19B H 0.6330 0.4602 0.6406 0.235 Uiso 0.5 1 calc R U P B 1 C20 C 0.8280(16) 0.4481(5) 0.533(2) 0.198(4) Uani 0.5 1 d D U P B 1 H20A H 0.9196 0.4589 0.5960 0.298 Uiso 0.5 1 calc R U P B 1 H20B H 0.8105 0.4555 0.3954 0.298 Uiso 0.5 1 calc R U P B 1 H20C H 0.8189 0.4114 0.5524 0.298 Uiso 0.5 1 calc R U P B 1 C15' C 0.646(3) 0.5848(7) 1.142(5) 0.202(5) Uani 0.4 1 d D U P B 2 H15C H 0.6617 0.5753 1.2798 0.242 Uiso 0.4 1 calc R U P B 2 H15D H 0.5532 0.5741 1.0809 0.242 Uiso 0.4 1 calc R U P B 2 C16' C 0.741(2) 0.5503(8) 1.055(2) 0.208(4) Uani 0.4 1 d D U P B 2 H16C H 0.8245 0.5692 1.0509 0.250 Uiso 0.4 1 calc R U P B 2 H16D H 0.7675 0.5199 1.1375 0.250 Uiso 0.4 1 calc R U P B 2 C17' C 0.6711(19) 0.5339(9) 0.856(2) 0.214(4) Uani 0.4 1 d D U P B 2 H17C H 0.6307 0.5643 0.7823 0.257 Uiso 0.4 1 calc R U P B 2 H17D H 0.5967 0.5106 0.8644 0.257 Uiso 0.4 1 calc R U P B 2 C18' C 0.768(2) 0.5057(6) 0.736(2) 0.225(4) Uani 0.5 1 d D U P B 2 H18C H 0.7442 0.5216 0.6071 0.270 Uiso 0.5 1 calc R U P B 2 H18D H 0.8596 0.5178 0.7968 0.270 Uiso 0.5 1 calc R U P B 2 C19' C 0.785(2) 0.4504(6) 0.697(2) 0.234(4) Uani 0.5 1 d D U P B 2 H19C H 0.7637 0.4286 0.7992 0.281 Uiso 0.5 1 calc R U P B 2 H19D H 0.8776 0.4429 0.6844 0.281 Uiso 0.5 1 calc R U P B 2 C20' C 0.678(2) 0.4439(7) 0.499(2) 0.245(5) Uani 0.5 1 d D U P B 2 H20D H 0.6034 0.4677 0.4942 0.368 Uiso 0.5 1 calc R U P B 2 H20E H 0.6435 0.4089 0.4886 0.368 Uiso 0.5 1 calc R U P B 2 H20F H 0.7209 0.4509 0.3930 0.368 Uiso 0.5 1 calc R U P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.1145(16) 0.162(2) 0.1239(17) 0.0201(14) 0.0047(12) 0.0524(14) F1 0.0628(11) 0.231(3) 0.1141(15) -0.0097(14) 0.0012(10) -0.0419(13) O1 0.0782(14) 0.200(3) 0.0740(14) -0.0190(14) -0.0112(11) -0.0024(14) C1 0.0521(13) 0.0957(18) 0.0572(14) 0.0021(12) 0.0072(10) -0.0063(12) C10 0.0517(13) 0.0892(17) 0.0574(14) 0.0038(11) 0.0080(10) -0.0024(11) C6 0.0553(14) 0.0980(19) 0.0657(15) 0.0079(13) 0.0124(11) -0.0044(12) C9 0.0578(14) 0.0930(18) 0.0556(14) 0.0022(12) 0.0052(11) -0.0023(12) C2 0.0624(15) 0.144(3) 0.0628(16) -0.0095(16) 0.0058(12) -0.0069(16) C8 0.0738(17) 0.116(2) 0.0604(15) -0.0090(14) 0.0098(13) -0.0006(15) C5 0.0501(14) 0.138(3) 0.084(2) 0.0107(17) 0.0149(13) 0.0003(14) C7 0.0666(16) 0.114(2) 0.0730(17) -0.0046(15) 0.0212(13) 0.0061(14) C13 0.0556(15) 0.142(3) 0.083(2) 0.0008(17) 0.0171(13) -0.0037(15) C14 0.0577(15) 0.125(2) 0.0641(16) -0.0076(15) 0.0110(12) -0.0019(14) C11 0.0658(16) 0.112(2) 0.0614(16) 0.0030(14) -0.0026(12) -0.0063(14) C12 0.0529(15) 0.126(3) 0.086(2) 0.0074(17) 0.0000(13) -0.0049(15) C4 0.0504(15) 0.170(3) 0.090(2) 0.015(2) -0.0002(15) -0.0111(17) C3 0.0668(18) 0.178(3) 0.0680(18) -0.0087(19) -0.0032(14) -0.0159(19) C15 0.066(3) 0.112(4) 0.127(4) -0.046(3) 0.033(3) -0.005(3) C16 0.111(3) 0.131(4) 0.141(4) -0.047(3) 0.039(3) 0.004(3) C17 0.154(4) 0.151(4) 0.166(4) -0.057(4) 0.037(3) 0.013(3) C18 0.184(5) 0.164(5) 0.184(5) -0.054(5) 0.027(4) 0.021(4) C19 0.206(6) 0.180(6) 0.192(6) -0.047(5) 0.028(5) 0.022(5) C20 0.229(8) 0.197(8) 0.179(7) -0.054(6) 0.065(7) 0.040(7) C15' 0.235(10) 0.186(8) 0.168(8) -0.067(7) 0.016(7) 0.064(8) C16' 0.244(10) 0.192(8) 0.172(7) -0.066(7) 0.016(7) 0.061(7) C17' 0.256(9) 0.197(7) 0.171(7) -0.060(6) 0.014(6) 0.058(7) C18' 0.272(9) 0.202(7) 0.178(7) -0.056(6) 0.007(6) 0.054(7) C19' 0.280(10) 0.209(7) 0.189(7) -0.047(6) 0.005(7) 0.052(7) C20' 0.295(12) 0.206(9) 0.204(9) -0.045(8) -0.004(9) 0.033(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C6 117.7(2) C2 C1 C10 122.9(2) C6 C1 C10 119.4(2) C9 C10 C1 117.8(2) C9 C10 C14 122.0(2) C1 C10 C14 120.2(2) C7 C6 C5 121.0(3) C7 C6 C1 119.8(2) C5 C6 C1 119.2(2) C10 C9 C8 121.6(2) C10 C9 C11 121.2(2) C8 C9 C11 117.2(2) C3 C2 C1 121.1(3) C3 C2 H2 119.5 C1 C2 H2 119.5 C7 C8 C9 120.9(2) C7 C8 H8 119.6 C9 C8 H8 119.6 C4 C5 C6 121.3(3) C4 C5 H5 119.4 C6 C5 H5 119.4 C8 C7 C6 120.4(3) C8 C7 H7 119.8 C6 C7 H7 119.8 C12 C13 C14 113.1(2) C12 C13 H13A 108.9 C14 C13 H13A 108.9 C12 C13 H13B 108.9 C14 C13 H13B 108.9 H13A C13 H13B 107.8 C15 C14 C10 112.8(4) C15 C14 C13 113.2(4) C10 C14 C13 111.3(2) C10 C14 C15' 109.1(9) C13 C14 C15' 113.3(11) C15 C14 H14 106.3 C10 C14 H14 106.3 C13 C14 H14 106.3 O1 C11 C9 123.0(3) O1 C11 C12 119.1(2) C9 C11 C12 117.9(2) F2 C12 F1 104.5(2) F2 C12 C13 112.4(3) F1 C12 C13 110.0(3) F2 C12 C11 106.5(3) F1 C12 C11 107.9(3) C13 C12 C11 114.9(2) C5 C4 C3 120.1(3) C5 C4 H4 120.0 C3 C4 H4 120.0 C2 C3 C4 120.7(3) C2 C3 H3 119.7 C4 C3 H3 119.7 C14 C15 C16 109.0(6) C14 C15 H15A 109.9 C16 C15 H15A 109.9 C14 C15 H15B 109.9 C16 C15 H15B 109.9 H15A C15 H15B 108.3 C17 C16 C15 107.8(7) C17 C16 H16A 110.1 C15 C16 H16A 110.1 C17 C16 H16B 110.1 C15 C16 H16B 110.1 H16A C16 H16B 108.5 C16 C17 C18 117.0(8) C16 C17 H17A 108.0 C18 C17 H17A 108.0 C16 C17 H17B 108.0 C18 C17 H17B 108.0 H17A C17 H17B 107.3 C19 C18 C17 98.6(9) C19 C18 H18A 112.1 C17 C18 H18A 112.1 C19 C18 H18B 112.1 C17 C18 H18B 112.1 H18A C18 H18B 109.7 C18 C19 C20 90.2(9) C18 C19 H19A 113.6 C20 C19 H19A 113.6 C18 C19 H19B 113.6 C20 C19 H19B 113.6 H19A C19 H19B 110.9 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 C16' C15' C14 124.4(18) C16' C15' H15C 106.2 C14 C15' H15C 106.2 C16' C15' H15D 106.2 C14 C15' H15D 106.2 H15C C15' H15D 106.4 C17' C16' C15' 110.0(19) C17' C16' H16C 109.7 C15' C16' H16C 109.7 C17' C16' H16D 109.7 C15' C16' H16D 109.7 H16C C16' H16D 108.2 C16' C17' C18' 114.5(14) C16' C17' H17C 108.6 C18' C17' H17C 108.6 C16' C17' H17D 108.6 C18' C17' H17D 108.6 H17C C17' H17D 107.6 C19' C18' C17' 130.8(19) C19' C18' H18C 104.6 C17' C18' H18C 104.6 C19' C18' H18D 104.6 C17' C18' H18D 104.6 H18C C18' H18D 105.7 C18' C19' C20' 100.6(13) C18' C19' H19C 111.7 C20' C19' H19C 111.7 C18' C19' H19D 111.7 C20' C19' H19D 111.7 H19C C19' H19D 109.4 C19' C20' H20D 109.5 C19' C20' H20E 109.5 H20D C20' H20E 109.5 C19' C20' H20F 109.5 H20D C20' H20F 109.5 H20E C20' H20F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F2 C12 1.355(4) F1 C12 1.365(3) O1 C11 1.209(3) C1 C2 1.410(4) C1 C6 1.416(4) C1 C10 1.441(3) C10 C9 1.384(3) C10 C14 1.504(4) C6 C7 1.406(4) C6 C5 1.416(4) C9 C8 1.406(4) C9 C11 1.470(3) C2 C3 1.368(4) C2 H2 0.9300 C8 C7 1.349(4) C8 H8 0.9300 C5 C4 1.342(4) C5 H5 0.9300 C7 H7 0.9300 C13 C12 1.481(4) C13 C14 1.535(4) C13 H13A 0.9700 C13 H13B 0.9700 C14 C15 1.502(8) C14 C15' 1.550(17) C14 H14 0.9800 C11 C12 1.518(4) C4 C3 1.392(5) C4 H4 0.9300 C3 H3 0.9300 C15 C16 1.569(10) C15 H15A 0.9700 C15 H15B 0.9700 C16 C17 1.528(10) C16 H16A 0.9700 C16 H16B 0.9700 C17 C18 1.605(12) C17 H17A 0.9700 C17 H17B 0.9700 C18 C19 1.510(14) C18 H18A 0.9700 C18 H18B 0.9700 C19 C20 1.700(14) C19 H19A 0.9700 C19 H19B 0.9700 C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 C15' C16' 1.531(17) C15' H15C 0.9700 C15' H15D 0.9700 C16' C17' 1.473(15) C16' H16C 0.9700 C16' H16D 0.9700 C17' C18' 1.594(15) C17' H17C 0.9700 C17' H17D 0.9700 C18' C19' 1.466(15) C18' H18C 0.9700 C18' H18D 0.9700 C19' C20' 1.551(15) C19' H19C 0.9700 C19' H19D 0.9700 C20' H20D 0.9600 C20' H20E 0.9600 C20' H20F 0.9600 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 C13 H13B O1 0.97 2.61 3.520(5) 156.3 4_575 C13 H13B O1 0.97 2.61 3.520(5) 156.3 4_575 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 C2 C1 C10 C9 179.5(3) C6 C1 C10 C9 0.9(4) C2 C1 C10 C14 -0.5(4) C6 C1 C10 C14 -179.0(3) C2 C1 C6 C7 -179.8(3) C10 C1 C6 C7 -1.2(4) C2 C1 C6 C5 -1.0(4) C10 C1 C6 C5 177.6(3) C1 C10 C9 C8 -0.3(4) C14 C10 C9 C8 179.7(3) C1 C10 C9 C11 -179.8(2) C14 C10 C9 C11 0.2(4) C6 C1 C2 C3 0.7(5) C10 C1 C2 C3 -177.9(3) C10 C9 C8 C7 -0.1(4) C11 C9 C8 C7 179.4(3) C7 C6 C5 C4 179.6(3) C1 C6 C5 C4 0.9(5) C9 C8 C7 C6 -0.1(5) C5 C6 C7 C8 -177.9(3) C1 C6 C7 C8 0.8(4) C9 C10 C14 C15 102.0(6) C1 C10 C14 C15 -78.0(6) C9 C10 C14 C13 -26.5(4) C1 C10 C14 C13 153.5(3) C9 C10 C14 C15' 99.3(13) C1 C10 C14 C15' -80.7(13) C12 C13 C14 C15 -79.0(6) C12 C13 C14 C10 49.4(4) C12 C13 C14 C15' -74.1(12) C10 C9 C11 O1 -175.5(3) C8 C9 C11 O1 4.9(4) C10 C9 C11 C12 3.9(4) C8 C9 C11 C12 -175.6(3) C14 C13 C12 F2 75.2(3) C14 C13 C12 F1 -168.8(3) C14 C13 C12 C11 -46.8(4) O1 C11 C12 F2 74.4(4) C9 C11 C12 F2 -105.1(3) O1 C11 C12 F1 -37.2(4) C9 C11 C12 F1 143.3(3) O1 C11 C12 C13 -160.4(3) C9 C11 C12 C13 20.1(4) C6 C5 C4 C3 -0.3(5) C1 C2 C3 C4 -0.1(6) C5 C4 C3 C2 -0.1(6) C10 C14 C15 C16 159.5(5) C13 C14 C15 C16 -73.0(8) C15' C14 C15 C16 -165(18) C14 C15 C16 C17 176.1(8) C15 C16 C17 C18 -165.4(8) C16 C17 C18 C19 -87.6(14) C17 C18 C19 C20 -174.6(10) C15 C14 C15' C16' 37(16) C10 C14 C15' C16' -177(2) C13 C14 C15' C16' -53(3) C14 C15' C16' C17' -95(3) C15' C16' C17' C18' 170.3(16) C16' C17' C18' C19' 101(3) C17' C18' C19' C20' 92(2)