#------------------------------------------------------------------------------ #$Date: 2025-08-21 22:26:11 +0100 (Thu, 21 Aug 2025) $ #$Revision: 301853 $ #$URL: svn://www.crystallography.net/cod/cif/7/10/89/7108926.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_7108926 loop_ _publ_author_name 'Poh Wai Chia' 'Davide Bello' 'Alexandra M. Z. Slawin' 'David O'Hagan' _publ_section_title ; Fluorinated 5- and 7-membered carbacycle motifs by reaction of difluorocarbene with acetylene ethers ; _journal_issue 22 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 2189 _journal_page_last 2191 _journal_paper_doi 10.1039/c3cc39066g _journal_volume 49 _journal_year 2013 _chemical_formula_moiety 'C19 H10 Br2 F6 O2' _chemical_formula_sum 'C19 H10 Br2 F6 O2' _chemical_formula_weight 544.09 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 115.201(10) _cell_angle_beta 90.957(10) _cell_angle_gamma 98.891(9) _cell_formula_units_Z 2 _cell_length_a 5.512(2) _cell_length_b 13.104(7) _cell_length_c 14.668(8) _cell_measurement_reflns_used 2851 _cell_measurement_temperature 93 _cell_measurement_theta_max 25.35 _cell_measurement_theta_min 1.54 _cell_volume 943.1(8) _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13' _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13' _computing_molecular_graphics 'CrystalStructure 4.0' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'DIRDIF99-PATTY (Gould, et al., 1999)' _diffrn_ambient_temperature 93 _diffrn_detector_area_resol_mean 14.629 _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 6092 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.36 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 4.381 _exptl_absorpt_correction_T_max 0.916 _exptl_absorpt_correction_T_min 0.488 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.916 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 528.00 _exptl_crystal_size_max 0.060 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.670 _refine_diff_density_min -0.650 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 262 _refine_ls_number_reflns 3342 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0539 _refine_ls_shift/su_max 0.007 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0423P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1210 _reflns_number_gt 2201 _reflns_number_total 3342 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file c3cc39066g.txt _cod_data_source_block 4b _cod_original_cell_volume 943.0(8) _cod_database_code 7108926 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z 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 Br11 Br -0.78401(11) 0.12641(5) 0.05535(5) 0.0433(3) Uani 1.0 2 d . Br17 Br 0.80463(13) 1.41585(6) 0.37952(6) 0.0535(3) Uani 1.0 2 d . F1 F -0.0420(7) 0.7569(3) 0.1043(3) 0.0478(10) Uani 1.0 2 d . F2 F -0.2872(6) 0.8341(3) 0.2173(3) 0.0478(10) Uani 1.0 2 d . F3 F 0.2589(7) 0.8975(3) 0.5122(3) 0.0497(10) Uani 1.0 2 d . F4 F -0.1434(6) 0.8605(4) 0.4394(3) 0.0515(11) Uani 1.0 2 d . F5 F 0.3510(6) 0.7156(4) 0.3718(3) 0.0603(12) Uani 1.0 2 d . F6 F 0.0078(7) 0.6949(3) 0.4570(3) 0.0468(10) Uani 1.0 2 d . O1 O -0.2765(8) 0.5978(4) 0.1261(4) 0.0504(13) Uani 1.0 2 d . O3 O 0.2147(8) 0.9388(4) 0.2128(3) 0.0440(11) Uani 1.0 2 d . C1 C -0.1396(9) 0.6755(5) 0.2122(5) 0.0262(13) Uani 1.0 2 d . C2 C -0.0774(10) 0.7858(5) 0.2025(5) 0.0276(14) Uani 1.0 2 d . C3 C 0.1366(10) 0.8790(5) 0.2655(5) 0.0260(13) Uani 1.0 2 d . C4 C 0.2273(11) 0.9030(6) 0.3574(5) 0.0426(17) Uani 1.0 2 d . C5 C 0.1315(17) 0.8455(7) 0.4198(6) 0.081(3) Uani 1.0 2 d . C6 C 0.0718(18) 0.7305(8) 0.3847(6) 0.085(3) Uani 1.0 2 d . C7 C -0.0823(11) 0.6542(5) 0.2897(5) 0.0371(15) Uani 1.0 2 d . C8 C -0.3808(11) 0.4890(6) 0.1174(5) 0.0353(15) Uani 1.0 2 d . C9 C -0.2879(12) 0.3972(6) 0.0552(5) 0.0419(16) Uani 1.0 2 d . C10 C -0.4033(11) 0.2888(6) 0.0380(5) 0.0396(16) Uani 1.0 2 d . C11 C -0.6141(10) 0.2759(5) 0.0848(5) 0.0330(15) Uani 1.0 2 d . C12 C -0.7053(11) 0.3692(6) 0.1491(5) 0.0452(18) Uani 1.0 2 d . C13 C -0.5892(12) 0.4776(6) 0.1637(6) 0.052(2) Uani 1.0 2 d . C14 C 0.3565(10) 1.0482(5) 0.2602(5) 0.0307(14) Uani 1.0 2 d . C15 C 0.2693(10) 1.1370(6) 0.3352(5) 0.0345(15) Uani 1.0 2 d . C16 C 0.4040(11) 1.2459(5) 0.3703(5) 0.0331(15) Uani 1.0 2 d . C17 C 0.6220(10) 1.2646(5) 0.3308(5) 0.0312(14) Uani 1.0 2 d . C18 C 0.7101(10) 1.1759(6) 0.2576(5) 0.0355(16) Uani 1.0 2 d . C19 C 0.5774(11) 1.0667(6) 0.2225(5) 0.0352(15) Uani 1.0 2 d . H4 H 0.3667 0.9627 0.3859 0.0511 Uiso 1.0 2 calc R H7 H -0.1493 0.5799 0.2832 0.0445 Uiso 1.0 2 calc R H9 H -0.1433 0.4071 0.0234 0.0502 Uiso 1.0 2 calc R H10 H -0.3388 0.2235 -0.0055 0.0476 Uiso 1.0 2 calc R H12 H -0.8460 0.3601 0.1833 0.0543 Uiso 1.0 2 calc R H13 H -0.6544 0.5434 0.2057 0.0623 Uiso 1.0 2 calc R H15 H 0.1189 1.1232 0.3622 0.0414 Uiso 1.0 2 calc R H16 H 0.3466 1.3084 0.4219 0.0397 Uiso 1.0 2 calc R H18 H 0.8617 1.1897 0.2314 0.0426 Uiso 1.0 2 calc R H19 H 0.6378 1.0042 0.1723 0.0423 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br11 0.0527(4) 0.0325(5) 0.0406(5) -0.0125(3) -0.0060(4) 0.0192(4) Br17 0.0700(5) 0.0323(5) 0.0511(6) -0.0215(4) -0.0133(4) 0.0223(4) F1 0.068(3) 0.039(3) 0.022(3) -0.0244(18) -0.0082(18) 0.0114(18) F2 0.0347(19) 0.030(2) 0.076(3) 0.0002(17) -0.0112(18) 0.022(2) F3 0.072(3) 0.036(3) 0.031(3) -0.0172(19) -0.0237(19) 0.0157(19) F4 0.047(2) 0.074(3) 0.047(3) 0.030(2) 0.0218(19) 0.032(3) F5 0.041(2) 0.088(4) 0.047(3) 0.031(3) -0.0011(19) 0.019(3) F6 0.070(3) 0.042(3) 0.029(3) -0.0135(19) -0.0038(18) 0.0237(19) O1 0.068(3) 0.031(3) 0.043(3) -0.028(3) -0.032(3) 0.021(3) O3 0.067(3) 0.033(3) 0.024(3) -0.025(3) -0.010(2) 0.016(3) C1 0.024(3) 0.018(4) 0.025(4) -0.006(3) -0.004(3) 0.001(3) C2 0.034(4) 0.027(4) 0.024(4) 0.002(3) 0.003(3) 0.015(3) C3 0.029(3) 0.024(4) 0.022(4) -0.006(3) -0.001(3) 0.011(3) C4 0.044(4) 0.038(4) 0.043(5) -0.021(3) -0.015(4) 0.025(4) C5 0.137(8) 0.049(6) 0.037(5) -0.059(5) -0.048(5) 0.026(5) C6 0.146(8) 0.060(6) 0.031(5) -0.054(6) -0.027(5) 0.030(5) C7 0.054(4) 0.025(4) 0.025(4) -0.013(3) -0.009(3) 0.011(3) C8 0.039(4) 0.028(4) 0.034(4) -0.015(3) -0.021(3) 0.017(4) C9 0.052(4) 0.033(4) 0.031(4) -0.011(4) -0.004(4) 0.010(4) C10 0.043(4) 0.032(4) 0.033(4) -0.005(3) 0.000(3) 0.009(4) C11 0.033(4) 0.026(4) 0.035(4) -0.009(3) -0.011(3) 0.014(3) C12 0.040(4) 0.031(4) 0.054(5) 0.007(4) 0.007(4) 0.008(4) C13 0.051(4) 0.021(4) 0.062(6) 0.002(4) -0.008(4) 0.000(4) C14 0.043(4) 0.022(4) 0.022(4) -0.017(3) -0.013(3) 0.013(3) C15 0.034(4) 0.038(4) 0.033(4) -0.003(3) 0.001(3) 0.021(4) C16 0.048(4) 0.022(4) 0.030(4) 0.007(3) 0.007(3) 0.011(3) C17 0.037(4) 0.023(4) 0.029(4) -0.011(3) -0.010(3) 0.013(3) C18 0.030(4) 0.045(5) 0.040(5) -0.005(3) 0.002(3) 0.031(4) C19 0.044(4) 0.031(4) 0.032(4) 0.002(3) 0.001(3) 0.016(4) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Br Br -0.2901 2.4595 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, 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 _geom_angle_publ_flag C1 O1 C8 120.1(6) yes C3 O3 C14 121.4(5) yes O1 C1 C2 107.4(6) yes O1 C1 C7 124.2(6) yes C2 C1 C7 128.4(5) yes F1 C2 F2 104.6(5) yes F1 C2 C1 106.4(5) yes F1 C2 C3 107.3(5) yes F2 C2 C1 107.3(5) yes F2 C2 C3 107.7(5) yes C1 C2 C3 122.3(6) yes O3 C3 C2 107.9(6) yes O3 C3 C4 124.7(5) yes C2 C3 C4 127.3(7) yes C3 C4 C5 125.8(6) yes F3 C5 F4 105.5(6) yes F3 C5 C4 109.5(6) yes F3 C5 C6 113.4(9) yes F4 C5 C4 110.1(8) yes F4 C5 C6 91.9(7) yes C4 C5 C6 123.6(7) yes F5 C6 F6 104.2(7) yes F5 C6 C5 92.2(7) yes F5 C6 C7 110.0(6) yes F6 C6 C5 114.0(7) yes F6 C6 C7 108.8(7) yes C5 C6 C7 124.5(10) yes C1 C7 C6 128.6(7) yes O1 C8 C9 119.1(6) yes O1 C8 C13 118.9(6) yes C9 C8 C13 121.6(7) yes C8 C9 C10 119.7(7) yes C9 C10 C11 119.3(6) yes Br11 C11 C10 119.4(5) yes Br11 C11 C12 119.7(5) yes C10 C11 C12 120.8(6) yes C11 C12 C13 118.9(7) yes C8 C13 C12 119.5(6) yes O3 C14 C15 121.4(5) yes O3 C14 C19 117.2(5) yes C15 C14 C19 121.1(6) yes C14 C15 C16 118.8(6) yes C15 C16 C17 120.0(5) yes Br17 C17 C16 119.4(4) yes Br17 C17 C18 119.5(5) yes C16 C17 C18 121.1(6) yes C17 C18 C19 119.4(6) yes C14 C19 C18 119.7(6) yes C3 C4 H4 117.123 no C5 C4 H4 117.126 no C1 C7 H7 115.689 no C6 C7 H7 115.686 no C8 C9 H9 120.133 no C10 C9 H9 120.132 no C9 C10 H10 120.336 no C11 C10 H10 120.337 no C11 C12 H12 120.540 no C13 C12 H12 120.539 no C8 C13 H13 120.243 no C12 C13 H13 120.248 no C14 C15 H15 120.620 no C16 C15 H15 120.612 no C15 C16 H16 120.021 no C17 C16 H16 120.016 no C17 C18 H18 120.311 no C19 C18 H18 120.311 no C14 C19 H19 120.159 no C18 C19 H19 120.165 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br11 C11 1.898(6) yes Br17 C17 1.899(6) yes F1 C2 1.351(7) yes F2 C2 1.380(7) yes F3 C5 1.352(9) yes F4 C5 1.574(11) yes F5 C6 1.586(11) yes F6 C6 1.360(11) yes O1 C1 1.355(6) yes O1 C8 1.403(9) yes O3 C3 1.348(9) yes O3 C14 1.392(7) yes C1 C2 1.500(10) yes C1 C7 1.325(11) yes C2 C3 1.515(7) yes C3 C4 1.317(10) yes C4 C5 1.472(13) yes C5 C6 1.350(12) yes C6 C7 1.474(9) yes C8 C9 1.346(9) yes C8 C13 1.365(10) yes C9 C10 1.377(10) yes C10 C11 1.383(9) yes C11 C12 1.364(9) yes C12 C13 1.389(10) yes C14 C15 1.377(8) yes C14 C19 1.376(9) yes C15 C16 1.374(8) yes C16 C17 1.376(9) yes C17 C18 1.367(8) yes C18 C19 1.372(9) yes C4 H4 0.950 no C7 H7 0.950 no C9 H9 0.950 no C10 H10 0.950 no C12 H12 0.950 no C13 H13 0.950 no C15 H15 0.950 no C16 H16 0.950 no C18 H18 0.950 no C19 H19 0.950 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_2 F1 O1 2.422(7) no . F1 O3 2.422(5) no . F1 C4 3.541(7) no . F1 C7 3.507(9) no . F2 F4 3.200(6) no . F2 O1 2.813(6) no . F2 O3 2.906(6) no . F2 C4 3.243(7) no . F2 C7 3.299(9) no . F3 F5 2.532(5) no . F3 F6 2.572(5) no . F3 C3 3.569(8) no . F4 F5 3.479(6) no . F4 F6 2.549(7) no . F4 C1 3.182(6) no . F4 C2 3.228(8) no . F4 C3 3.081(8) no . F4 C7 2.737(7) no . F5 C1 3.372(7) no . F5 C3 3.461(9) no . F5 C4 2.738(10) no . F6 C1 3.561(8) no . C1 C4 3.178(7) no . C1 C5 3.084(9) no . C1 C9 3.337(8) no . C1 C13 3.123(8) no . C2 C5 3.094(11) no . C2 C6 3.178(13) no . C3 C6 3.111(13) no . C3 C7 3.173(10) no . C3 C15 3.046(9) no . C3 C19 3.446(9) no . C4 C7 3.161(9) no . C4 C14 2.844(11) no . C4 C15 3.193(11) no . C7 C8 2.808(8) no . C7 C13 3.281(8) no . C8 C11 2.722(9) no . C9 C12 2.756(10) no . C10 C13 2.745(9) no . C14 C17 2.724(8) no . C15 C18 2.767(9) no . C16 C19 2.750(8) no . Br11 Br11 3.4832(15) no 2_355 Br11 F1 3.488(5) no 2_465 Br11 C19 3.541(8) no 1_445 Br17 F6 3.327(4) no 1_665 Br17 F6 3.502(5) no 2_676 F1 Br11 3.488(5) no 2_465 F1 C9 3.180(7) no 2_565 F1 C10 3.495(8) no 2_465 F1 C10 3.210(8) no 2_565 F1 C11 3.166(8) no 2_465 F1 C12 3.517(8) no 2_465 F2 O3 3.264(6) no 1_455 F2 C3 3.351(7) no 1_455 F2 C4 3.399(7) no 1_455 F2 C14 3.516(8) no 1_455 F2 C19 3.218(9) no 1_455 F3 F4 3.521(6) no 1_655 F3 F4 3.113(7) no 2_576 F3 C4 3.433(6) no 2_676 F4 F3 3.521(6) no 1_455 F4 F3 3.113(7) no 2_576 F4 F4 3.408(6) no 2_576 F4 F5 3.004(5) no 1_455 F4 C4 3.365(7) no 2_576 F4 C5 3.501(9) no 2_576 F4 C15 3.377(9) no 2_576 F5 F4 3.004(5) no 1_655 F5 C7 3.454(7) no 1_655 F5 C13 3.375(7) no 1_655 F6 Br17 3.327(4) no 1_445 F6 Br17 3.502(5) no 2_676 F6 C15 3.457(7) no 2_576 F6 C16 3.351(7) no 2_576 F6 C17 3.490(8) no 2_676 O1 C9 3.582(9) no 2_465 O3 F2 3.264(6) no 1_655 C3 F2 3.351(7) no 1_655 C4 F2 3.399(7) no 1_655 C4 F3 3.433(6) no 2_676 C4 F4 3.365(7) no 2_576 C5 F4 3.501(9) no 2_576 C7 F5 3.454(7) no 1_455 C9 F1 3.180(7) no 2_565 C9 O1 3.582(9) no 2_465 C10 F1 3.495(8) no 2_465 C10 F1 3.210(8) no 2_565 C11 F1 3.166(8) no 2_465 C12 F1 3.517(8) no 2_465 C13 F5 3.375(7) no 1_455 C14 F2 3.516(8) no 1_655 C15 F4 3.377(9) no 2_576 C15 F6 3.457(7) no 2_576 C15 C18 3.452(9) no 1_455 C16 F6 3.351(7) no 2_576 C17 F6 3.490(8) no 2_676 C18 C15 3.452(9) no 1_655 C19 Br11 3.541(8) no 1_665 C19 F2 3.218(9) no 1_655 Br11 H10 2.9177 no . Br11 H12 2.9102 no . Br17 H16 2.9052 no . Br17 H18 2.9039 no . F3 H4 2.3970 no . F4 H4 3.1813 no . F4 H7 3.3993 no . F5 H4 3.1429 no . F5 H7 2.9751 no . F6 H7 2.4023 no . O1 H7 2.5130 no . O1 H9 2.5398 no . O1 H13 2.5567 no . O3 H4 2.5335 no . O3 H15 2.6162 no . O3 H19 2.5278 no . C1 H9 3.4234 no . C1 H13 3.0636 no . C2 H4 3.3642 no . C2 H7 3.3527 no . C3 H15 2.9150 no . C3 H19 3.5809 no . C4 H15 3.0082 no . C5 H7 3.2885 no . C6 H4 3.2131 no . C7 H13 3.2406 no . C8 H7 2.4337 no . C8 H10 3.2133 no . C8 H12 3.2398 no . C9 H7 3.1670 no . C9 H13 3.2198 no . C10 H12 3.2483 no . C11 H9 3.2431 no . C11 H13 3.2316 no . C12 H10 3.2446 no . C13 H7 2.7567 no . C13 H9 3.2220 no . C14 H4 2.5373 no . C14 H16 3.2292 no . C14 H18 3.2369 no . C15 H4 2.8057 no . C15 H19 3.2523 no . C16 H18 3.2447 no . C17 H15 3.2427 no . C17 H19 3.2247 no . C18 H16 3.2414 no . C19 H4 3.3678 no . C19 H15 3.2551 no . H4 H15 2.8118 no . H7 H9 3.5113 no . H7 H13 2.8794 no . H9 H10 2.3333 no . H12 H13 2.3510 no . H15 H16 2.3329 no . H18 H19 2.3290 no . Br11 H18 3.1644 no 1_345 Br11 H19 3.2216 no 2_565 Br17 H7 3.0184 no 1_665 Br17 H12 3.3696 no 1_765 F1 H9 2.5465 no 2_565 F1 H10 2.6119 no 2_565 F2 H4 3.1934 no 1_455 F2 H10 3.4309 no 2_465 F2 H19 2.6641 no 1_455 F3 H4 2.4990 no 2_676 F3 H15 2.8600 no 2_576 F4 H4 3.4120 no 1_455 F4 H4 3.0626 no 2_576 F4 H15 2.8246 no 2_576 F5 H7 3.4782 no 1_655 F5 H13 2.5142 no 1_655 F5 H16 3.5832 no 2_676 F6 H15 2.8975 no 2_576 F6 H16 2.6698 no 2_576 O1 H9 3.2036 no 2_565 O3 H10 3.0409 no 2_565 O3 H19 3.5225 no 1_455 C1 H13 3.3843 no 1_655 C2 H9 3.5783 no 2_565 C5 H15 3.3914 no 2_576 C6 H13 3.3132 no 1_655 C7 H13 2.9698 no 1_655 C9 H12 3.2692 no 1_655 C10 H12 3.4713 no 1_655 C12 H9 3.2366 no 1_455 C13 H9 3.4226 no 1_455 C15 H18 3.0174 no 1_455 C16 H18 3.3866 no 1_455 C18 H15 3.0289 no 1_655 C19 H15 3.3880 no 1_655 H4 F2 3.1934 no 1_655 H4 F3 2.4990 no 2_676 H4 F4 3.4120 no 1_655 H4 F4 3.0626 no 2_576 H4 H4 3.3045 no 2_676 H7 Br17 3.0184 no 1_445 H7 F5 3.4782 no 1_455 H7 H12 3.3486 no 1_655 H7 H13 3.0014 no 1_655 H9 F1 2.5465 no 2_565 H9 O1 3.2036 no 2_565 H9 C2 3.5783 no 2_565 H9 C12 3.2366 no 1_655 H9 C13 3.4226 no 1_655 H9 H9 3.0271 no 2_565 H9 H12 3.1593 no 1_655 H9 H13 3.4357 no 1_655 H10 F1 2.6119 no 2_565 H10 F2 3.4309 no 2_465 H10 O3 3.0409 no 2_565 H10 H12 3.5044 no 1_655 H10 H19 3.1195 no 2_565 H12 Br17 3.3696 no 1_345 H12 C9 3.2692 no 1_455 H12 C10 3.4713 no 1_455 H12 H7 3.3486 no 1_455 H12 H9 3.1593 no 1_455 H12 H10 3.5044 no 1_455 H12 H18 2.8896 no 1_345 H13 F5 2.5142 no 1_455 H13 C1 3.3843 no 1_455 H13 C6 3.3132 no 1_455 H13 C7 2.9698 no 1_455 H13 H7 3.0014 no 1_455 H13 H9 3.4357 no 1_455 H15 F3 2.8600 no 2_576 H15 F4 2.8246 no 2_576 H15 F6 2.8975 no 2_576 H15 C5 3.3914 no 2_576 H15 C18 3.0289 no 1_455 H15 C19 3.3880 no 1_455 H15 H18 2.8576 no 1_455 H15 H19 3.4638 no 1_455 H16 F5 3.5832 no 2_676 H16 F6 2.6698 no 2_576 H16 H18 3.4838 no 1_455 H18 Br11 3.1644 no 1_765 H18 C15 3.0174 no 1_655 H18 C16 3.3866 no 1_655 H18 H12 2.8896 no 1_765 H18 H15 2.8576 no 1_655 H18 H16 3.4838 no 1_655 H19 Br11 3.2216 no 2_565 H19 F2 2.6641 no 1_655 H19 O3 3.5225 no 1_655 H19 H10 3.1195 no 2_565 H19 H15 3.4638 no 1_655 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_publ_flag C1 O1 C8 C9 -108.7(6) no C1 O1 C8 C13 78.1(7) no C8 O1 C1 C2 -174.2(4) no C8 O1 C1 C7 4.1(8) no C3 O3 C14 C15 -60.4(9) no C3 O3 C14 C19 125.6(6) no C14 O3 C3 C2 160.8(5) no C14 O3 C3 C4 -16.3(8) no O1 C1 C2 F1 -35.9(6) no O1 C1 C2 F2 75.5(5) no O1 C1 C2 C3 -159.5(4) no O1 C1 C7 C6 177.6(5) no C2 C1 C7 C6 -4.5(10) no C7 C1 C2 F1 145.8(6) no C7 C1 C2 F2 -102.7(7) no C7 C1 C2 C3 22.3(9) no F1 C2 C3 O3 29.7(6) no F1 C2 C3 C4 -153.2(5) no F2 C2 C3 O3 -82.4(6) no F2 C2 C3 C4 94.7(7) no C1 C2 C3 O3 152.8(5) no C1 C2 C3 C4 -30.1(8) no O3 C3 C4 C5 174.4(5) no C2 C3 C4 C5 -2.3(10) no C3 C4 C5 F3 -175.8(6) no C3 C4 C5 F4 -60.2(8) no C3 C4 C5 C6 46.4(12) no F3 C5 C6 F5 -68.6(8) no F3 C5 C6 F6 38.0(11) no F3 C5 C6 C7 175.2(7) no F4 C5 C6 F5 -176.4(5) no F4 C5 C6 F6 -69.8(8) no F4 C5 C6 C7 67.4(9) no C4 C5 C6 F5 67.8(10) no C4 C5 C6 F6 174.4(8) no C4 C5 C6 C7 -48.3(14) no F5 C6 C7 C1 -89.9(9) no F6 C6 C7 C1 156.5(6) no C5 C6 C7 C1 17.5(13) no O1 C8 C9 C10 -173.5(6) no O1 C8 C13 C12 174.9(6) no C9 C8 C13 C12 1.9(11) no C13 C8 C9 C10 -0.5(11) no C8 C9 C10 C11 0.2(11) no C9 C10 C11 Br11 176.5(6) no C9 C10 C11 C12 -1.4(10) no Br11 C11 C12 C13 -175.1(5) no C10 C11 C12 C13 2.8(11) no C11 C12 C13 C8 -3.0(11) no O3 C14 C15 C16 -172.0(6) no O3 C14 C19 C18 171.9(6) no C15 C14 C19 C18 -2.1(11) no C19 C14 C15 C16 1.8(11) no C14 C15 C16 C17 -0.2(11) no C15 C16 C17 Br17 179.6(6) no C15 C16 C17 C18 -1.0(11) no Br17 C17 C18 C19 -179.9(5) no C16 C17 C18 C19 0.6(11) no C17 C18 C19 C14 0.9(11) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 102205220