# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2023 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_cu_WCH-xray-B_0m _database_code_depnum_ccdc_archive 'CCDC 2215186' loop_ _audit_author_name _audit_author_address 'Jordi Benet Buchholz' ;ICIQ Spain ; _audit_update_record ; 2022-10-25 deposited with the CCDC. 2023-04-04 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H11 F21 O' _chemical_formula_weight 678.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 21' _space_group_name_Hall 'P 2yb' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.6498(2) _cell_length_b 9.6522(3) _cell_length_c 22.2488(6) _cell_angle_alpha 90 _cell_angle_beta 92.285(2) _cell_angle_gamma 90 _cell_volume 1212.33(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8532 _cell_measurement_theta_min 3.98 _cell_measurement_theta_max 67.64 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.858 _exptl_crystal_F_000 668 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.010 _exptl_absorpt_coefficient_mu 2.088 _shelx_estimated_absorpt_T_min 0.818 _shelx_estimated_absorpt_T_max 0.979 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6282 _exptl_absorpt_correction_T_max 0.7530 _exptl_absorpt_process_details SADABS-2016/2 _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source 'Microfocus source E025 IuS' _diffrn_source_type 'Bruker APEX DUO' _diffrn_source_power 50 _diffrn_source_current 0.65 _diffrn_source_size '0.2 mm x 0.2 mm fine focus' _diffrn_radiation_monochromator 'Quazar MX Multilayer Optics' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'APEX DUO Kappa 4-axis goniometer' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 14295 _diffrn_reflns_av_unetI/netI 0.0370 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.987 _diffrn_reflns_theta_max 67.986 _diffrn_reflns_theta_full 67.679 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measured_fraction_theta_full 0.970 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_Laue_measured_fraction_full 0.970 _diffrn_reflns_point_group_measured_fraction_max 0.946 _diffrn_reflns_point_group_measured_fraction_full 0.948 _reflns_number_total 4183 _reflns_number_gt 3926 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.834 _reflns_Friedel_fraction_max 0.918 _reflns_Friedel_fraction_full 0.922 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Bruker APEX2 v2014.9-0' _computing_cell_refinement 'Bruker APEX2 v2014.9-0' _computing_data_reduction 'Bruker APEX2 v2014.9-0' _computing_structure_solution 'SHELXT (Sheldrick, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'shelXle (H\"ubschle, Sheldrick and Dittirch, 2011)' _computing_publication_material 'SHELXL-2018/3 (Sheldrick, 2018)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.8294P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 1673 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.00(6) _chemical_absolute_configuration ad _refine_ls_number_reflns 4183 _refine_ls_number_parameters 389 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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_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 F1 F 0.0067(5) 0.2089(3) 0.20375(12) 0.0346(7) Uani 1 1 d . . . . . F3 F 0.3879(6) 0.1957(3) 0.27166(12) 0.0390(7) Uani 1 1 d . . . . . F4 F 0.4674(5) 0.4156(3) 0.26196(12) 0.0380(7) Uani 1 1 d . . . . . F5 F -0.0535(5) 0.2912(3) 0.31993(12) 0.0351(7) Uani 1 1 d . . . . . F6 F 0.1223(6) 0.4917(3) 0.32680(12) 0.0399(8) Uani 1 1 d . . . . . F7 F 0.5194(5) 0.3366(4) 0.37930(12) 0.0436(8) Uani 1 1 d . . . . . F8 F 0.2651(6) 0.1689(3) 0.38765(12) 0.0397(8) Uani 1 1 d . . . . . F9 F -0.0391(5) 0.3796(4) 0.43610(12) 0.0429(8) Uani 1 1 d . . . . . F10 F 0.2809(7) 0.5048(3) 0.44408(12) 0.0438(8) Uani 1 1 d . . . . . F11 F 0.1487(7) 0.1823(3) 0.50337(12) 0.0487(9) Uani 1 1 d . . . . . F12 F 0.5038(6) 0.2661(4) 0.49742(14) 0.0526(10) Uani 1 1 d . . . . . F13 F 0.0344(8) 0.4529(4) 0.55074(14) 0.0663(13) Uani 1 1 d . . . . . F14 F 0.4133(9) 0.4756(4) 0.56298(14) 0.0693(13) Uani 1 1 d . . . . . F15 F 0.0208(7) 0.2354(5) 0.61655(14) 0.0635(12) Uani 1 1 d . . . . . F16 F 0.3942(8) 0.2030(4) 0.61617(14) 0.0622(12) Uani 1 1 d . . . . . F17 F 0.4897(8) 0.4167(5) 0.68258(15) 0.0693(12) Uani 1 1 d . . . . . F18 F 0.1366(10) 0.5023(4) 0.66766(15) 0.0800(16) Uani 1 1 d . . . . . F19 F 0.2903(9) 0.1960(4) 0.73967(15) 0.0719(12) Uani 1 1 d . . . . . F20 F 0.2329(9) 0.3963(4) 0.77809(14) 0.0706(13) Uani 1 1 d . . . . . F21 F -0.0496(9) 0.2932(7) 0.73016(17) 0.0951(18) Uani 1 1 d . . . . . O1 O -0.0385(6) 0.5492(3) -0.03713(14) 0.0305(8) Uani 1 1 d . . . . . C1 C -0.0430(8) 0.4648(5) 0.00300(19) 0.0239(9) Uani 1 1 d . . . . . H1 H -0.146517 0.387705 -0.002040 0.029 Uiso 1 1 calc R U . . . F2 F -0.0175(5) 0.4337(3) 0.21144(11) 0.0329(6) Uani 1 1 d . . . . . C2 C 0.1040(8) 0.4747(4) 0.05966(18) 0.0217(9) Uani 1 1 d . . . . . C3 C 0.2481(8) 0.6013(4) 0.07049(19) 0.0227(9) Uani 1 1 d . . . . . C4 C 0.4421(8) 0.6274(5) 0.03596(19) 0.0246(9) Uani 1 1 d . . . . . H4 H 0.476825 0.566319 0.004023 0.030 Uiso 1 1 calc R U . . . C5 C 0.5868(9) 0.7421(5) 0.0474(2) 0.0281(10) Uani 1 1 d . . . . . H5 H 0.721250 0.757577 0.024006 0.034 Uiso 1 1 calc R U . . . C6 C 0.5343(9) 0.8332(5) 0.09296(19) 0.0270(10) Uani 1 1 d . . . . . H6 H 0.631546 0.911938 0.100824 0.032 Uiso 1 1 calc R U . . . C7 C 0.3381(9) 0.8086(5) 0.1271(2) 0.0295(10) Uani 1 1 d . . . . . H7 H 0.300126 0.871653 0.158015 0.035 Uiso 1 1 calc R U . . . C8 C 0.1971(9) 0.6929(5) 0.11644(19) 0.0268(10) Uani 1 1 d . . . . . H8 H 0.065311 0.676107 0.140634 0.032 Uiso 1 1 calc R U . . . C9 C 0.1058(8) 0.3652(5) 0.09610(18) 0.0213(9) Uani 1 1 d . . . . . H9 H -0.007479 0.294336 0.087800 0.026 Uiso 1 1 calc R U . . . C10 C 0.2745(8) 0.3459(5) 0.14955(18) 0.0247(10) Uani 1 1 d . . . . . H10 H 0.373734 0.431343 0.154180 0.030 Uiso 1 1 calc R U . . . C11 C 0.1367(8) 0.3271(5) 0.20675(19) 0.0234(9) Uani 1 1 d . . . . . C12 C 0.2916(8) 0.3231(5) 0.2658(2) 0.0260(10) Uani 1 1 d . . . . . C13 C 0.1588(8) 0.3543(5) 0.32395(19) 0.0230(9) Uani 1 1 d . . . . . C14 C 0.2897(8) 0.3073(5) 0.3827(2) 0.0249(9) Uani 1 1 d . . . . . C15 C 0.1984(8) 0.3743(5) 0.44042(19) 0.0243(10) Uani 1 1 d . . . . . C16 C 0.2728(8) 0.2982(5) 0.49974(19) 0.0241(9) Uani 1 1 d . . . . . C17 C 0.2376(10) 0.3846(5) 0.5570(2) 0.0321(11) Uani 1 1 d . . . . . C18 C 0.2313(9) 0.3000(5) 0.6159(2) 0.0308(11) Uani 1 1 d . . . . . C19 C 0.2588(11) 0.3858(6) 0.6736(2) 0.0396(13) Uani 1 1 d . . . . . C20 C 0.1812(12) 0.3156(8) 0.7318(2) 0.0517(16) Uani 1 1 d . . . . . C21 C 0.4390(9) 0.2230(5) 0.1378(2) 0.0331(11) Uani 1 1 d . . . . . H21A H 0.550744 0.211000 0.172241 0.050 Uiso 1 1 calc R U . . . H21B H 0.526865 0.240914 0.101510 0.050 Uiso 1 1 calc R U . . . H21C H 0.344331 0.138550 0.132167 0.050 Uiso 1 1 calc R U . . . 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 0.0405(17) 0.0346(16) 0.0286(14) 0.0029(12) -0.0009(11) -0.0135(13) F3 0.0520(19) 0.0409(17) 0.0240(13) 0.0033(12) -0.0008(12) 0.0209(15) F4 0.0345(17) 0.0547(19) 0.0248(13) 0.0002(13) -0.0003(11) -0.0207(14) F5 0.0240(15) 0.0547(19) 0.0266(14) 0.0019(13) 0.0002(10) -0.0067(13) F6 0.068(2) 0.0257(15) 0.0260(14) 0.0018(12) 0.0000(13) 0.0150(14) F7 0.0213(15) 0.086(3) 0.0235(13) 0.0038(15) -0.0002(10) -0.0024(15) F8 0.072(2) 0.0215(15) 0.0254(14) 0.0015(12) -0.0039(13) 0.0095(13) F9 0.0311(17) 0.074(2) 0.0231(14) -0.0014(14) -0.0006(11) 0.0139(15) F10 0.081(3) 0.0231(15) 0.0274(14) 0.0016(11) -0.0014(14) -0.0123(14) F11 0.091(3) 0.0302(16) 0.0251(14) -0.0011(13) 0.0000(15) -0.0271(17) F12 0.041(2) 0.088(3) 0.0280(14) 0.0051(16) -0.0027(12) 0.0277(18) F13 0.093(3) 0.080(3) 0.0249(15) -0.0015(17) -0.0029(16) 0.060(2) F14 0.119(4) 0.057(2) 0.0313(16) 0.0011(16) -0.0063(18) -0.057(2) F15 0.075(3) 0.085(3) 0.0309(17) 0.0039(17) 0.0047(16) -0.044(2) F16 0.109(3) 0.049(2) 0.0290(16) 0.0034(15) -0.0014(17) 0.044(2) F17 0.088(3) 0.078(3) 0.0399(19) -0.0057(19) -0.0152(18) -0.032(2) F18 0.162(5) 0.046(2) 0.0305(17) -0.0080(15) -0.017(2) 0.054(3) F19 0.131(4) 0.050(2) 0.0340(18) 0.0123(17) -0.003(2) 0.019(2) F20 0.112(4) 0.074(3) 0.0239(16) -0.0092(17) -0.0135(18) 0.028(2) F21 0.079(3) 0.172(6) 0.034(2) -0.001(3) 0.0101(18) -0.009(3) O1 0.041(2) 0.0265(18) 0.0230(16) 0.0062(14) -0.0071(14) 0.0004(14) C1 0.024(3) 0.023(2) 0.024(2) -0.0040(18) -0.0027(17) 0.0046(17) F2 0.0381(17) 0.0360(15) 0.0249(13) 0.0041(12) 0.0039(11) 0.0143(12) C2 0.025(2) 0.021(2) 0.019(2) -0.0028(17) 0.0022(16) 0.0046(17) C3 0.030(3) 0.020(2) 0.018(2) 0.0039(17) -0.0020(17) 0.0026(17) C4 0.031(3) 0.022(2) 0.021(2) 0.0009(17) 0.0028(17) 0.0007(18) C5 0.030(3) 0.029(3) 0.025(2) 0.0034(19) 0.0051(18) -0.0021(19) C6 0.035(3) 0.022(2) 0.023(2) 0.0017(18) -0.0071(17) -0.0063(19) C7 0.045(3) 0.022(2) 0.022(2) -0.0033(18) 0.0005(19) 0.000(2) C8 0.034(3) 0.025(2) 0.021(2) -0.0001(18) 0.0029(17) 0.0005(19) C9 0.020(2) 0.023(2) 0.021(2) -0.0007(18) 0.0044(16) -0.0004(17) C10 0.026(2) 0.027(2) 0.021(2) 0.0003(18) -0.0013(17) -0.0018(19) C11 0.028(2) 0.019(2) 0.023(2) 0.0006(17) -0.0022(17) -0.0029(18) C12 0.028(3) 0.025(2) 0.025(2) 0.0055(18) -0.0008(17) 0.0028(19) C13 0.027(3) 0.020(2) 0.022(2) 0.0032(17) -0.0024(17) -0.0021(17) C14 0.026(3) 0.025(2) 0.024(2) 0.0017(18) -0.0032(17) 0.0029(18) C15 0.023(3) 0.024(2) 0.025(2) 0.0018(18) -0.0003(17) 0.0011(18) C16 0.026(3) 0.024(2) 0.022(2) 0.0011(18) -0.0013(16) 0.0001(18) C17 0.044(3) 0.023(3) 0.029(3) 0.0016(19) 0.001(2) -0.002(2) C18 0.046(3) 0.019(2) 0.027(2) 0.0011(19) -0.002(2) -0.001(2) C19 0.053(4) 0.033(3) 0.031(3) 0.001(2) -0.011(2) 0.007(2) C20 0.067(4) 0.062(4) 0.026(3) -0.005(3) -0.005(2) 0.013(3) C21 0.039(3) 0.036(3) 0.025(2) -0.004(2) -0.0007(19) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C11 1.357(5) . ? F3 C12 1.349(5) . ? F4 C12 1.341(5) . ? F5 C13 1.345(5) . ? F6 C13 1.344(5) . ? F7 C14 1.333(6) . ? F8 C14 1.347(6) . ? F9 C15 1.342(6) . ? F10 C15 1.344(6) . ? F11 C16 1.324(6) . ? F12 C16 1.344(6) . ? F13 C17 1.326(6) . ? F14 C17 1.329(6) . ? F15 C18 1.343(6) . ? F16 C18 1.313(6) . ? F17 C19 1.345(7) . ? F18 C19 1.323(7) . ? F19 C20 1.317(8) . ? F20 C20 1.314(7) . ? F21 C20 1.321(8) . ? O1 C1 1.210(5) . ? C1 C2 1.485(6) . ? C1 H1 0.9500 . ? F2 C11 1.355(5) . ? C2 C9 1.331(6) . ? C2 C3 1.483(6) . ? C3 C4 1.386(6) . ? C3 C8 1.390(6) . ? C4 C5 1.393(7) . ? C4 H4 0.9500 . ? C5 C6 1.383(7) . ? C5 H5 0.9500 . ? C6 C7 1.389(7) . ? C6 H6 0.9500 . ? C7 C8 1.387(7) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.506(6) . ? C9 H9 0.9500 . ? C10 C11 1.529(6) . ? C10 C21 1.536(6) . ? C10 H10 1.0000 . ? C11 C12 1.550(6) . ? C12 C13 1.551(6) . ? C13 C14 1.545(6) . ? C14 C15 1.544(6) . ? C15 C16 1.554(6) . ? C16 C17 1.541(6) . ? C17 C18 1.546(7) . ? C18 C19 1.531(7) . ? C19 C20 1.542(9) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 O1 C1 C2 123.7(4) . . ? O1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C9 C2 C3 124.4(4) . . ? C9 C2 C1 117.1(4) . . ? C3 C2 C1 118.4(4) . . ? C4 C3 C8 118.9(4) . . ? C4 C3 C2 120.1(4) . . ? C8 C3 C2 121.0(4) . . ? C3 C4 C5 120.9(4) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 119.9(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 119.4(4) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 120.7(4) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C3 120.2(4) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? C2 C9 C10 124.6(4) . . ? C2 C9 H9 117.7 . . ? C10 C9 H9 117.7 . . ? C9 C10 C11 110.2(3) . . ? C9 C10 C21 109.2(4) . . ? C11 C10 C21 112.4(4) . . ? C9 C10 H10 108.3 . . ? C11 C10 H10 108.3 . . ? C21 C10 H10 108.3 . . ? F2 C11 F1 107.1(3) . . ? F2 C11 C10 108.9(3) . . ? F1 C11 C10 110.6(3) . . ? F2 C11 C12 107.3(3) . . ? F1 C11 C12 107.9(3) . . ? C10 C11 C12 114.8(3) . . ? F4 C12 F3 108.4(4) . . ? F4 C12 C11 108.9(3) . . ? F3 C12 C11 108.5(4) . . ? F4 C12 C13 107.9(4) . . ? F3 C12 C13 107.6(3) . . ? C11 C12 C13 115.3(4) . . ? F6 C13 F5 108.2(4) . . ? F6 C13 C14 108.6(4) . . ? F5 C13 C14 108.6(3) . . ? F6 C13 C12 108.1(4) . . ? F5 C13 C12 108.4(4) . . ? C14 C13 C12 114.7(4) . . ? F7 C14 F8 108.6(4) . . ? F7 C14 C15 108.5(4) . . ? F8 C14 C15 108.0(4) . . ? F7 C14 C13 108.8(4) . . ? F8 C14 C13 108.2(4) . . ? C15 C14 C13 114.6(4) . . ? F9 C15 F10 108.1(4) . . ? F9 C15 C14 108.8(4) . . ? F10 C15 C14 108.4(4) . . ? F9 C15 C16 108.3(4) . . ? F10 C15 C16 108.1(4) . . ? C14 C15 C16 114.8(4) . . ? F11 C16 F12 109.0(4) . . ? F11 C16 C17 108.7(4) . . ? F12 C16 C17 108.3(4) . . ? F11 C16 C15 109.0(4) . . ? F12 C16 C15 107.8(4) . . ? C17 C16 C15 114.0(4) . . ? F13 C17 F14 108.8(5) . . ? F13 C17 C16 108.8(4) . . ? F14 C17 C16 108.7(4) . . ? F13 C17 C18 107.6(4) . . ? F14 C17 C18 107.8(4) . . ? C16 C17 C18 115.0(4) . . ? F16 C18 F15 106.8(5) . . ? F16 C18 C19 109.5(4) . . ? F15 C18 C19 107.6(4) . . ? F16 C18 C17 110.0(4) . . ? F15 C18 C17 107.8(4) . . ? C19 C18 C17 114.9(4) . . ? F18 C19 F17 109.0(5) . . ? F18 C19 C18 109.9(4) . . ? F17 C19 C18 108.1(5) . . ? F18 C19 C20 107.0(5) . . ? F17 C19 C20 106.2(5) . . ? C18 C19 C20 116.4(5) . . ? F20 C20 F19 109.1(5) . . ? F20 C20 F21 107.9(5) . . ? F19 C20 F21 108.5(7) . . ? F20 C20 C19 109.6(6) . . ? F19 C20 C19 110.4(5) . . ? F21 C20 C19 111.2(5) . . ? C10 C21 H21A 109.5 . . ? C10 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C10 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C9 -170.9(4) . . . . ? O1 C1 C2 C3 5.9(6) . . . . ? C9 C2 C3 C4 107.3(5) . . . . ? C1 C2 C3 C4 -69.3(5) . . . . ? C9 C2 C3 C8 -70.4(6) . . . . ? C1 C2 C3 C8 113.0(5) . . . . ? C8 C3 C4 C5 1.0(7) . . . . ? C2 C3 C4 C5 -176.7(4) . . . . ? C3 C4 C5 C6 -1.5(7) . . . . ? C4 C5 C6 C7 0.5(7) . . . . ? C5 C6 C7 C8 0.9(7) . . . . ? C6 C7 C8 C3 -1.3(7) . . . . ? C4 C3 C8 C7 0.3(7) . . . . ? C2 C3 C8 C7 178.1(4) . . . . ? C3 C2 C9 C10 -7.8(7) . . . . ? C1 C2 C9 C10 168.8(4) . . . . ? C2 C9 C10 C11 122.4(4) . . . . ? C2 C9 C10 C21 -113.7(5) . . . . ? C9 C10 C11 F2 -53.0(5) . . . . ? C21 C10 C11 F2 -175.1(4) . . . . ? C9 C10 C11 F1 64.4(5) . . . . ? C21 C10 C11 F1 -57.7(5) . . . . ? C9 C10 C11 C12 -173.3(4) . . . . ? C21 C10 C11 C12 64.6(5) . . . . ? F2 C11 C12 F4 -82.6(4) . . . . ? F1 C11 C12 F4 162.4(4) . . . . ? C10 C11 C12 F4 38.6(5) . . . . ? F2 C11 C12 F3 159.6(3) . . . . ? F1 C11 C12 F3 44.5(5) . . . . ? C10 C11 C12 F3 -79.2(4) . . . . ? F2 C11 C12 C13 38.9(5) . . . . ? F1 C11 C12 C13 -76.2(5) . . . . ? C10 C11 C12 C13 160.1(4) . . . . ? F4 C12 C13 F6 45.4(5) . . . . ? F3 C12 C13 F6 162.3(4) . . . . ? C11 C12 C13 F6 -76.5(5) . . . . ? F4 C12 C13 F5 162.5(4) . . . . ? F3 C12 C13 F5 -80.6(4) . . . . ? C11 C12 C13 F5 40.5(5) . . . . ? F4 C12 C13 C14 -75.9(5) . . . . ? F3 C12 C13 C14 40.9(5) . . . . ? C11 C12 C13 C14 162.1(4) . . . . ? F6 C13 C14 F7 -79.8(5) . . . . ? F5 C13 C14 F7 162.8(4) . . . . ? C12 C13 C14 F7 41.3(5) . . . . ? F6 C13 C14 F8 162.3(4) . . . . ? F5 C13 C14 F8 44.9(5) . . . . ? C12 C13 C14 F8 -76.6(5) . . . . ? F6 C13 C14 C15 41.8(5) . . . . ? F5 C13 C14 C15 -75.6(5) . . . . ? C12 C13 C14 C15 162.9(4) . . . . ? F7 C14 C15 F9 162.8(4) . . . . ? F8 C14 C15 F9 -79.6(5) . . . . ? C13 C14 C15 F9 41.0(5) . . . . ? F7 C14 C15 F10 45.4(5) . . . . ? F8 C14 C15 F10 162.9(4) . . . . ? C13 C14 C15 F10 -76.4(5) . . . . ? F7 C14 C15 C16 -75.6(5) . . . . ? F8 C14 C15 C16 42.0(5) . . . . ? C13 C14 C15 C16 162.6(4) . . . . ? F9 C15 C16 F11 48.4(5) . . . . ? F10 C15 C16 F11 165.4(4) . . . . ? C14 C15 C16 F11 -73.5(5) . . . . ? F9 C15 C16 F12 166.6(4) . . . . ? F10 C15 C16 F12 -76.5(5) . . . . ? C14 C15 C16 F12 44.7(5) . . . . ? F9 C15 C16 C17 -73.2(5) . . . . ? F10 C15 C16 C17 43.8(5) . . . . ? C14 C15 C16 C17 165.0(4) . . . . ? F11 C16 C17 F13 -81.3(5) . . . . ? F12 C16 C17 F13 160.4(5) . . . . ? C15 C16 C17 F13 40.4(6) . . . . ? F11 C16 C17 F14 160.4(4) . . . . ? F12 C16 C17 F14 42.1(5) . . . . ? C15 C16 C17 F14 -77.9(5) . . . . ? F11 C16 C17 C18 39.4(6) . . . . ? F12 C16 C17 C18 -78.8(5) . . . . ? C15 C16 C17 C18 161.2(4) . . . . ? F13 C17 C18 F16 162.7(4) . . . . ? F14 C17 C18 F16 -80.1(5) . . . . ? C16 C17 C18 F16 41.3(6) . . . . ? F13 C17 C18 F15 46.7(5) . . . . ? F14 C17 C18 F15 163.8(4) . . . . ? C16 C17 C18 F15 -74.7(5) . . . . ? F13 C17 C18 C19 -73.2(6) . . . . ? F14 C17 C18 C19 44.0(6) . . . . ? C16 C17 C18 C19 165.4(5) . . . . ? F16 C18 C19 F18 164.9(5) . . . . ? F15 C18 C19 F18 -79.3(6) . . . . ? C17 C18 C19 F18 40.7(7) . . . . ? F16 C18 C19 F17 46.1(6) . . . . ? F15 C18 C19 F17 161.8(5) . . . . ? C17 C18 C19 F17 -78.2(6) . . . . ? F16 C18 C19 C20 -73.2(6) . . . . ? F15 C18 C19 C20 42.5(6) . . . . ? C17 C18 C19 C20 162.5(5) . . . . ? F18 C19 C20 F20 -61.9(7) . . . . ? F17 C19 C20 F20 54.5(7) . . . . ? C18 C19 C20 F20 174.8(5) . . . . ? F18 C19 C20 F19 177.9(5) . . . . ? F17 C19 C20 F19 -65.8(6) . . . . ? C18 C19 C20 F19 54.5(7) . . . . ? F18 C19 C20 F21 57.4(7) . . . . ? F17 C19 C20 F21 173.7(6) . . . . ? C18 C19 C20 F21 -66.0(7) . . . . ? _refine_diff_density_max 0.443 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.063 _shelx_res_file ; TITL cu_WCH-xray-B_0m in P2(1) cu_WCH-xray-B_0m.res created by SHELXL-2018/3 at 13:20:40 on 25-Oct-2022 CELL 1.54178 5.64980 9.65220 22.24880 90.0000 92.2846 90.0000 ZERR 2.00 0.00020 0.00030 0.00060 0.0000 0.0021 0.0000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H F O UNIT 42 22 42 2 TEMP -173.270 SIZE 0.01 0.10 0.10 L.S. 15 BOND $H LIST 4 ACTA CONF FMAP 2 PLAN 20 WGHT 0.062400 0.829400 FVAR 0.18451 MOLE 1 F1 3 0.006655 0.208938 0.203748 11.00000 0.04054 0.03464 = 0.02858 0.00294 -0.00087 -0.01351 F3 3 0.387870 0.195714 0.271660 11.00000 0.05202 0.04086 = 0.02404 0.00334 -0.00085 0.02091 F4 3 0.467388 0.415613 0.261956 11.00000 0.03447 0.05467 = 0.02479 0.00020 -0.00029 -0.02069 F5 3 -0.053491 0.291212 0.319927 11.00000 0.02398 0.05474 = 0.02664 0.00185 0.00024 -0.00673 F6 3 0.122286 0.491724 0.326804 11.00000 0.06778 0.02566 = 0.02600 0.00181 -0.00001 0.01495 F7 3 0.519360 0.336650 0.379298 11.00000 0.02133 0.08592 = 0.02349 0.00380 -0.00016 -0.00238 F8 3 0.265143 0.168935 0.387647 11.00000 0.07159 0.02150 = 0.02540 0.00145 -0.00388 0.00949 F9 3 -0.039072 0.379606 0.436096 11.00000 0.03112 0.07430 = 0.02311 -0.00137 -0.00059 0.01391 F10 3 0.280869 0.504772 0.444080 11.00000 0.08077 0.02307 = 0.02736 0.00156 -0.00136 -0.01230 F11 3 0.148664 0.182325 0.503374 11.00000 0.09069 0.03017 = 0.02509 -0.00108 -0.00004 -0.02706 F12 3 0.503811 0.266146 0.497424 11.00000 0.04115 0.08835 = 0.02800 0.00511 -0.00275 0.02772 F13 3 0.034420 0.452882 0.550742 11.00000 0.09321 0.08040 = 0.02491 -0.00153 -0.00291 0.05951 F14 3 0.413329 0.475585 0.562979 11.00000 0.11933 0.05658 = 0.03134 0.00110 -0.00632 -0.05745 F15 3 0.020833 0.235395 0.616551 11.00000 0.07499 0.08472 = 0.03089 0.00387 0.00475 -0.04439 F16 3 0.394186 0.202968 0.616173 11.00000 0.10876 0.04853 = 0.02898 0.00338 -0.00136 0.04350 F17 3 0.489666 0.416690 0.682580 11.00000 0.08843 0.07823 = 0.03991 -0.00573 -0.01519 -0.03159 F18 3 0.136629 0.502285 0.667661 11.00000 0.16196 0.04575 = 0.03054 -0.00796 -0.01687 0.05375 F19 3 0.290323 0.196032 0.739665 11.00000 0.13137 0.04968 = 0.03405 0.01230 -0.00260 0.01919 F20 3 0.232887 0.396320 0.778090 11.00000 0.11217 0.07449 = 0.02387 -0.00922 -0.01352 0.02820 F21 3 -0.049630 0.293198 0.730160 11.00000 0.07917 0.17249 = 0.03441 -0.00106 0.01005 -0.00926 O1 4 -0.038485 0.549249 -0.037132 11.00000 0.04143 0.02648 = 0.02298 0.00624 -0.00713 0.00038 C1 1 -0.043010 0.464761 0.002997 11.00000 0.02438 0.02291 = 0.02403 -0.00399 -0.00270 0.00457 AFIX 43 H1 2 -0.146517 0.387705 -0.002040 11.00000 -1.20000 AFIX 0 F2 3 -0.017538 0.433711 0.211436 11.00000 0.03808 0.03600 = 0.02490 0.00408 0.00393 0.01427 C2 1 0.104022 0.474682 0.059664 11.00000 0.02463 0.02116 = 0.01929 -0.00283 0.00221 0.00461 C3 1 0.248135 0.601303 0.070493 11.00000 0.02967 0.01999 = 0.01833 0.00389 -0.00200 0.00262 C4 1 0.442095 0.627440 0.035958 11.00000 0.03108 0.02181 = 0.02109 0.00094 0.00277 0.00071 AFIX 43 H4 2 0.476825 0.566319 0.004023 11.00000 -1.20000 AFIX 0 C5 1 0.586790 0.742060 0.047422 11.00000 0.03040 0.02904 = 0.02507 0.00341 0.00508 -0.00214 AFIX 43 H5 2 0.721250 0.757577 0.024006 11.00000 -1.20000 AFIX 0 C6 1 0.534293 0.833198 0.092956 11.00000 0.03504 0.02232 = 0.02296 0.00173 -0.00708 -0.00631 AFIX 43 H6 2 0.631546 0.911938 0.100824 11.00000 -1.20000 AFIX 0 C7 1 0.338133 0.808577 0.127073 11.00000 0.04458 0.02189 = 0.02192 -0.00328 0.00055 -0.00020 AFIX 43 H7 2 0.300126 0.871653 0.158015 11.00000 -1.20000 AFIX 0 C8 1 0.197140 0.692864 0.116444 11.00000 0.03390 0.02540 = 0.02113 -0.00007 0.00293 0.00049 AFIX 43 H8 2 0.065311 0.676107 0.140634 11.00000 -1.20000 AFIX 0 C9 1 0.105759 0.365249 0.096103 11.00000 0.01998 0.02306 = 0.02117 -0.00075 0.00436 -0.00045 AFIX 43 H9 2 -0.007479 0.294336 0.087800 11.00000 -1.20000 AFIX 0 C10 1 0.274508 0.345928 0.149547 11.00000 0.02618 0.02705 = 0.02078 0.00031 -0.00125 -0.00182 AFIX 13 H10 2 0.373734 0.431343 0.154180 11.00000 -1.20000 AFIX 0 C11 1 0.136673 0.327133 0.206749 11.00000 0.02779 0.01896 = 0.02305 0.00058 -0.00217 -0.00293 C12 1 0.291589 0.323115 0.265782 11.00000 0.02775 0.02484 = 0.02532 0.00552 -0.00082 0.00279 C13 1 0.158778 0.354331 0.323951 11.00000 0.02670 0.02031 = 0.02168 0.00316 -0.00239 -0.00211 C14 1 0.289717 0.307268 0.382740 11.00000 0.02604 0.02486 = 0.02356 0.00168 -0.00318 0.00290 C15 1 0.198438 0.374281 0.440421 11.00000 0.02329 0.02394 = 0.02545 0.00181 -0.00031 0.00109 C16 1 0.272803 0.298193 0.499743 11.00000 0.02588 0.02435 = 0.02185 0.00111 -0.00130 0.00005 C17 1 0.237583 0.384562 0.556968 11.00000 0.04430 0.02291 = 0.02920 0.00157 0.00140 -0.00167 C18 1 0.231321 0.299986 0.615871 11.00000 0.04593 0.01910 = 0.02696 0.00114 -0.00186 -0.00121 C19 1 0.258840 0.385843 0.673592 11.00000 0.05342 0.03329 = 0.03118 0.00072 -0.01052 0.00661 C20 1 0.181190 0.315598 0.731839 11.00000 0.06709 0.06183 = 0.02562 -0.00541 -0.00517 0.01250 C21 1 0.439001 0.222968 0.137803 11.00000 0.03860 0.03565 = 0.02502 -0.00432 -0.00066 0.00747 AFIX 137 H21A 2 0.550744 0.211000 0.172241 11.00000 -1.50000 H21B 2 0.526865 0.240914 0.101510 11.00000 -1.50000 H21C 2 0.344331 0.138550 0.132167 11.00000 -1.50000 AFIX 0 HKLF 4 REM cu_WCH-xray-B_0m in P2(1) REM wR2 = 0.118405, GooF = S = 1.07001, Restrained GooF = 1.06987 for all data REM R1 = 0.044439 for 3926 Fo > 4sig(Fo) and 0.047629 for all 4183 data REM 389 parameters refined using 1 restraints END WGHT 0.0624 0.8294 REM Highest difference peak 0.443, deepest hole -0.295, 1-sigma level 0.063 Q1 1 0.4660 0.4140 0.7324 11.00000 0.05 0.44 Q2 1 -0.0420 0.3582 0.5547 11.00000 0.05 0.42 Q3 1 -0.0371 0.2851 0.6694 11.00000 0.05 0.40 Q4 1 0.5105 0.3087 0.6225 11.00000 0.05 0.35 Q5 1 0.2308 0.3377 0.4095 11.00000 0.05 0.29 Q6 1 0.4647 0.4363 0.3768 11.00000 0.05 0.28 Q7 1 0.2344 0.3312 0.2980 11.00000 0.05 0.28 Q8 1 0.2392 0.3255 0.5312 11.00000 0.05 0.27 Q9 1 0.1615 0.1733 0.5419 11.00000 0.05 0.25 Q10 1 0.2550 0.3434 0.5838 11.00000 0.05 0.24 Q11 1 0.5076 0.3431 0.5122 11.00000 0.05 0.24 Q12 1 0.2269 0.3379 0.1809 11.00000 0.05 0.23 Q13 1 -0.1364 0.4173 0.2387 11.00000 0.05 0.22 Q14 1 0.2687 0.7463 0.1217 11.00000 0.05 0.22 Q15 1 -0.0160 0.2565 0.4288 11.00000 0.05 0.22 Q16 1 0.1738 0.5369 0.0664 11.00000 0.05 0.22 Q17 1 0.5002 0.2053 0.7362 11.00000 0.05 0.21 Q18 1 0.0519 0.4780 0.4408 11.00000 0.05 0.21 Q19 1 0.2702 0.1713 0.6454 11.00000 0.05 0.21 Q20 1 0.5437 0.1934 0.3890 11.00000 0.05 0.21 ; _shelx_res_checksum 61087 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: hexane and diethyl ether'