# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2022 ####################################################################### # # 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_ds10 _database_code_depnum_ccdc_archive 'CCDC 2180252' loop_ _audit_author_name _audit_author_address 'Serhii Vasylevskyi' ;OIST Okinawa Institute of Science and Technology Japan ; _audit_update_record ; 2022-06-20 deposited with the CCDC. 2022-10-14 downloaded from the CCDC. ; _audit_creation_date 2022-03-16 _audit_creation_method ; Olex2 1.5 (compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439) ; _shelx_SHELXL_version_number 2016/6 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C10 H9 F7 N2 O3' _chemical_formula_sum 'C10 H9 F7 N2 O3' _chemical_formula_weight 338.19 _chemical_melting_point ? _chemical_oxdiff_formula 'C11 H10 N O' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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. ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4543(9) _cell_length_b 8.9233(15) _cell_length_c 9.8274(14) _cell_angle_alpha 111.704(14) _cell_angle_beta 98.837(11) _cell_angle_gamma 101.362(11) _cell_volume 654.12(17) _cell_formula_units_Z 2 _cell_measurement_reflns_used 601 _cell_measurement_temperature 200.00(10) _cell_measurement_theta_max 19.4630 _cell_measurement_theta_min 2.3140 _shelx_estimated_absorpt_T_max 0.994 _shelx_estimated_absorpt_T_min 0.991 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.15382 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 340 _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.031 _exptl_crystal_size_min 0.03 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.1175 _diffrn_reflns_av_unetI/netI 0.1307 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7895 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.349 _diffrn_reflns_theta_min 2.303 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 200.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -69.30 20.70 0.50 1.00 -- 0.00 -59.58 -39.80 180 2 \w -19.70 70.30 0.50 1.00 -- 0.00 59.58 99.80 180 3 \w -69.30 20.70 0.50 1.00 -- 0.00 -59.58 80.20 180 4 \w -19.70 70.30 0.50 1.00 -- 0.00 59.58-140.20 180 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'Saxi-CrysAlisPro-abstract goniometer imported SAXI images' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0205724000 _diffrn_orient_matrix_UB_12 -0.0648697000 _diffrn_orient_matrix_UB_13 0.0248720000 _diffrn_orient_matrix_UB_21 0.0075422000 _diffrn_orient_matrix_UB_22 0.0608047000 _diffrn_orient_matrix_UB_23 0.0735561000 _diffrn_orient_matrix_UB_31 -0.0855889000 _diffrn_orient_matrix_UB_32 -0.0044556000 _diffrn_orient_matrix_UB_33 -0.0200800000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1140 _reflns_number_total 2392 _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. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2016/6 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _refine_diff_density_max 0.374 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.071 _refine_ls_extinction_coef 0.014(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 2392 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1604 _refine_ls_R_factor_gt 0.0649 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0543P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1367 _refine_ls_wR_factor_ref 0.1834 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.5 times of: All C(H,H,H) groups 2. Others Sof(F6B)=Sof(F7B)=1-FVAR(1) Sof(F6A)=Sof(F7A)=FVAR(1) 3.a Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary ? _atom_sites_solution_secondary ? 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 0.7356(3) 0.1025(3) 0.7805(3) 0.0426(8) Uani 1 1 d . . . . . F2 F 0.5117(3) 0.0493(3) 0.8550(3) 0.0451(8) Uani 1 1 d . . . . . F3 F 0.7575(4) 0.4498(4) 0.9416(3) 0.0783(12) Uani 1 1 d . . . . . F4 F 0.5561(4) 0.3682(4) 1.0308(3) 0.0736(11) Uani 1 1 d . . . . . F5 F 0.8412(5) 0.4425(5) 1.2216(4) 0.0876(13) Uani 1 1 d . . . . . O1 O 0.2624(4) 0.1476(4) 0.7722(4) 0.0485(10) Uani 1 1 d . . . . . O2 O 0.2432(4) 0.2681(4) 0.3626(4) 0.0484(10) Uani 1 1 d . . . . . O3 O 0.7463(4) 0.2571(4) 0.6062(4) 0.0438(9) Uani 1 1 d . . . . . N1 N 0.2505(4) 0.2085(5) 0.5648(5) 0.0419(11) Uani 1 1 d . . . . . N2 N 0.4977(4) 0.2629(5) 0.4801(4) 0.0365(10) Uani 1 1 d . . . . . C1 C 0.8042(7) 0.3101(7) 1.0926(6) 0.0500(14) Uani 1 1 d . . . . . C2 C 0.6828(6) 0.3230(6) 0.9687(6) 0.0451(13) Uani 1 1 d . . . . . C3 C 0.6061(5) 0.1651(6) 0.8202(5) 0.0367(12) Uani 1 1 d . . . . . C4 C 0.5101(5) 0.1931(6) 0.6953(5) 0.0324(11) Uani 1 1 d . . . . . C5 C 0.3388(6) 0.1836(6) 0.6740(5) 0.0390(12) Uani 1 1 d . . . . . C6 C 0.3365(6) 0.2457(6) 0.4729(5) 0.0410(12) Uani 1 1 d . . . . . C7 C 0.5824(5) 0.2373(5) 0.5923(5) 0.0346(11) Uani 1 1 d . . . . . C8 C 0.8183(6) 0.2966(7) 0.4946(5) 0.0495(14) Uani 1 1 d . . . . . H8A H 0.756996 0.212749 0.393029 0.074 Uiso 1 1 calc R U . . . H8B H 0.935323 0.295747 0.511586 0.074 Uiso 1 1 calc R U . . . H8C H 0.811115 0.408091 0.503669 0.074 Uiso 1 1 calc R U . . . C9 C 0.3232(6) 0.3026(7) 0.2540(6) 0.0530(15) Uani 1 1 d . . . . . H9A H 0.243526 0.321521 0.182750 0.079 Uiso 1 1 calc R U . . . H9B H 0.362514 0.206772 0.198696 0.079 Uiso 1 1 calc R U . . . H9C H 0.418150 0.402996 0.306675 0.079 Uiso 1 1 calc R U . . . C10 C 0.0851(5) 0.1276(7) 0.7472(6) 0.0536(15) Uani 1 1 d . . . . . H10A H 0.028240 0.039609 0.646203 0.080 Uiso 1 1 calc R U . . . H10B H 0.062522 0.233631 0.754800 0.080 Uiso 1 1 calc R U . . . H10C H 0.044196 0.095933 0.823534 0.080 Uiso 1 1 calc R U . . . F6A F 0.9505(9) 0.312(2) 1.0572(9) 0.080(4) Uani 0.85(4) 1 d . . P A 1 F7A F 0.7563(17) 0.1745(9) 1.1133(9) 0.070(3) Uani 0.85(4) 1 d . . P A 1 F6B F 0.894(8) 0.202(11) 1.062(6) 0.11(3) Uani 0.15(4) 1 d . . P A 2 F7B F 0.680(8) 0.221(9) 1.144(5) 0.074(18) Uani 0.15(4) 1 d . . P A 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 F1 0.0348(15) 0.055(2) 0.0465(17) 0.0243(15) 0.0122(12) 0.0217(14) F2 0.0423(16) 0.0430(18) 0.0521(17) 0.0240(15) 0.0102(13) 0.0087(13) F3 0.111(3) 0.045(2) 0.052(2) 0.0249(17) -0.0128(18) -0.0189(18) F4 0.075(2) 0.079(3) 0.056(2) 0.0069(18) 0.0135(17) 0.044(2) F5 0.118(3) 0.069(3) 0.045(2) 0.012(2) -0.0171(19) 0.011(2) O1 0.0322(19) 0.067(3) 0.050(2) 0.025(2) 0.0134(16) 0.0152(17) O2 0.044(2) 0.059(2) 0.047(2) 0.0251(19) 0.0034(17) 0.0226(18) O3 0.0291(18) 0.064(2) 0.046(2) 0.0292(18) 0.0111(15) 0.0147(17) N1 0.036(2) 0.042(3) 0.046(3) 0.015(2) 0.006(2) 0.015(2) N2 0.031(2) 0.041(3) 0.038(2) 0.019(2) 0.0055(18) 0.0094(19) C1 0.054(4) 0.041(4) 0.048(3) 0.021(3) -0.001(3) 0.002(3) C2 0.051(3) 0.041(3) 0.042(3) 0.019(3) 0.011(3) 0.007(3) C3 0.027(3) 0.040(3) 0.048(3) 0.023(3) 0.012(2) 0.009(2) C4 0.027(2) 0.038(3) 0.031(3) 0.013(2) 0.006(2) 0.011(2) C5 0.038(3) 0.042(3) 0.037(3) 0.016(2) 0.010(2) 0.013(2) C6 0.041(3) 0.033(3) 0.044(3) 0.012(2) 0.005(2) 0.011(2) C7 0.034(3) 0.030(3) 0.036(3) 0.011(2) 0.005(2) 0.009(2) C8 0.044(3) 0.066(4) 0.046(3) 0.030(3) 0.018(3) 0.012(3) C9 0.059(3) 0.057(4) 0.052(3) 0.033(3) 0.007(3) 0.021(3) C10 0.027(3) 0.072(4) 0.060(4) 0.025(3) 0.015(2) 0.013(3) F6A 0.035(3) 0.130(9) 0.067(4) 0.041(5) 0.004(2) 0.015(4) F7A 0.066(6) 0.070(4) 0.076(4) 0.048(3) -0.008(4) 0.005(4) F6B 0.05(3) 0.11(5) 0.10(3) -0.01(3) -0.03(2) 0.03(4) F7B 0.05(3) 0.11(3) 0.07(2) 0.07(2) -0.005(17) -0.01(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 C3 1.369(5) . ? F2 C3 1.357(5) . ? F3 C2 1.320(5) . ? F4 C2 1.368(6) . ? F5 C1 1.313(6) . ? O1 C5 1.338(5) . ? O1 C10 1.445(5) . ? O2 C6 1.340(5) . ? O2 C9 1.440(5) . ? O3 C7 1.341(5) . ? O3 C8 1.451(5) . ? N1 C5 1.325(5) . ? N1 C6 1.334(6) . ? N2 C6 1.329(5) . ? N2 C7 1.337(5) . ? C1 C2 1.522(7) . ? C1 F6A 1.334(8) . ? C1 F7A 1.298(8) . ? C1 F6B 1.32(4) . ? C1 F7B 1.46(4) . ? C2 C3 1.537(7) . ? C3 C4 1.492(6) . ? C4 C5 1.412(6) . ? C4 C7 1.394(6) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 C5 O1 C10 117.9(4) . . ? C6 O2 C9 117.5(4) . . ? C7 O3 C8 118.0(4) . . ? C5 N1 C6 114.7(4) . . ? C6 N2 C7 115.5(4) . . ? F5 C1 C2 112.4(5) . . ? F5 C1 F6A 103.2(7) . . ? F5 C1 F6B 123.4(14) . . ? F5 C1 F7B 90(3) . . ? F6A C1 C2 109.2(5) . . ? F7A C1 F5 110.0(6) . . ? F7A C1 C2 114.0(6) . . ? F7A C1 F6A 107.4(6) . . ? F6B C1 C2 122(2) . . ? F6B C1 F7B 98(3) . . ? F7B C1 C2 97(2) . . ? F3 C2 F4 106.5(4) . . ? F3 C2 C1 107.9(4) . . ? F3 C2 C3 110.4(4) . . ? F4 C2 C1 105.7(4) . . ? F4 C2 C3 108.1(4) . . ? C1 C2 C3 117.7(4) . . ? F1 C3 C2 106.0(4) . . ? F1 C3 C4 111.5(4) . . ? F2 C3 F1 104.9(4) . . ? F2 C3 C2 106.6(4) . . ? F2 C3 C4 112.2(3) . . ? C4 C3 C2 114.9(4) . . ? C5 C4 C3 123.1(4) . . ? C7 C4 C3 123.2(4) . . ? C7 C4 C5 113.7(4) . . ? O1 C5 C4 117.0(4) . . ? N1 C5 O1 118.5(4) . . ? N1 C5 C4 124.5(4) . . ? N1 C6 O2 113.3(4) . . ? N2 C6 O2 118.9(4) . . ? N2 C6 N1 127.9(4) . . ? O3 C7 C4 118.7(4) . . ? N2 C7 O3 117.6(4) . . ? N2 C7 C4 123.7(4) . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 H9A 109.5 . . ? O2 C9 H9B 109.5 . . ? O2 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 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 F1 C3 C4 C5 151.0(4) . . . . ? F1 C3 C4 C7 -31.6(6) . . . . ? F2 C3 C4 C5 33.6(6) . . . . ? F2 C3 C4 C7 -149.0(4) . . . . ? F3 C2 C3 F1 77.4(5) . . . . ? F3 C2 C3 F2 -171.1(4) . . . . ? F3 C2 C3 C4 -46.2(6) . . . . ? F4 C2 C3 F1 -166.5(3) . . . . ? F4 C2 C3 F2 -55.0(5) . . . . ? F4 C2 C3 C4 69.9(5) . . . . ? F5 C1 C2 F3 64.5(6) . . . . ? F5 C1 C2 F4 -49.1(6) . . . . ? F5 C1 C2 C3 -169.9(4) . . . . ? C1 C2 C3 F1 -47.0(6) . . . . ? C1 C2 C3 F2 64.4(5) . . . . ? C1 C2 C3 C4 -170.6(4) . . . . ? C2 C3 C4 C5 -88.4(5) . . . . ? C2 C3 C4 C7 89.1(6) . . . . ? C3 C4 C5 O1 0.0(7) . . . . ? C3 C4 C5 N1 179.6(5) . . . . ? C3 C4 C7 O3 -0.5(7) . . . . ? C3 C4 C7 N2 -179.9(4) . . . . ? C5 N1 C6 O2 179.2(4) . . . . ? C5 N1 C6 N2 -1.2(7) . . . . ? C5 C4 C7 O3 177.1(4) . . . . ? C5 C4 C7 N2 -2.2(7) . . . . ? C6 N1 C5 O1 179.2(4) . . . . ? C6 N1 C5 C4 -0.4(7) . . . . ? C6 N2 C7 O3 -178.5(4) . . . . ? C6 N2 C7 C4 0.9(7) . . . . ? C7 N2 C6 O2 -179.5(4) . . . . ? C7 N2 C6 N1 1.0(7) . . . . ? C7 C4 C5 O1 -177.7(4) . . . . ? C7 C4 C5 N1 2.0(7) . . . . ? C8 O3 C7 N2 -3.0(6) . . . . ? C8 O3 C7 C4 177.6(4) . . . . ? C9 O2 C6 N1 -177.7(4) . . . . ? C9 O2 C6 N2 2.6(7) . . . . ? C10 O1 C5 N1 3.9(7) . . . . ? C10 O1 C5 C4 -176.4(4) . . . . ? F6A C1 C2 F3 -49.5(10) . . . . ? F6A C1 C2 F4 -163.1(9) . . . . ? F6A C1 C2 C3 76.2(10) . . . . ? F7A C1 C2 F3 -169.6(9) . . . . ? F7A C1 C2 F4 76.8(9) . . . . ? F7A C1 C2 C3 -43.9(10) . . . . ? F6B C1 C2 F3 -98(6) . . . . ? F6B C1 C2 F4 148(6) . . . . ? F6B C1 C2 C3 27(6) . . . . ? F7B C1 C2 F3 157(4) . . . . ? F7B C1 C2 F4 44(4) . . . . ? F7B C1 C2 C3 -77(4) . . . . ? _shelx_res_file ; TITL mo_scan_a.res in P-1 ds10.res created by SHELXL-2016/6 at 17:32:07 on 16-Mar-2022 REM Old TITL mo_scan in P-1 REM SHELXT solution in P-1: R1 0.272, Rweak 0.067, Alpha 0.071 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C11 F5 N3 O3 CELL 0.71073 8.4543 8.9233 9.8274 111.704 98.837 101.362 ZERR 2 0.0009 0.0015 0.0014 0.014 0.011 0.011 LATT 1 SFAC C H F N O UNIT 20 18 14 4 6 L.S. 4 0 0 PLAN 5 SIZE 0.03 0.031 0.05 TEMP -73 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.054300 EXTI 0.013784 FVAR 4.40871 0.84622 F1 3 0.735600 0.102536 0.780494 11.00000 0.03482 0.05476 = 0.04653 0.02431 0.01219 0.02166 F2 3 0.511710 0.049309 0.854982 11.00000 0.04235 0.04296 = 0.05215 0.02404 0.01018 0.00872 F3 3 0.757489 0.449752 0.941599 11.00000 0.11128 0.04499 = 0.05230 0.02485 -0.01281 -0.01886 F4 3 0.556050 0.368197 1.030773 11.00000 0.07513 0.07944 = 0.05617 0.00691 0.01353 0.04365 F5 3 0.841201 0.442464 1.221553 11.00000 0.11764 0.06885 = 0.04523 0.01173 -0.01714 0.01135 O1 5 0.262390 0.147604 0.772184 11.00000 0.03218 0.06678 = 0.04953 0.02537 0.01344 0.01516 O2 5 0.243233 0.268092 0.362622 11.00000 0.04362 0.05868 = 0.04687 0.02506 0.00338 0.02263 O3 5 0.746345 0.257145 0.606223 11.00000 0.02906 0.06401 = 0.04578 0.02917 0.01108 0.01470 N1 4 0.250550 0.208519 0.564756 11.00000 0.03556 0.04197 = 0.04604 0.01537 0.00569 0.01517 N2 4 0.497664 0.262852 0.480150 11.00000 0.03093 0.04121 = 0.03846 0.01925 0.00551 0.00941 C1 1 0.804213 0.310102 1.092621 11.00000 0.05362 0.04061 = 0.04820 0.02134 -0.00116 0.00169 C2 1 0.682752 0.322977 0.968740 11.00000 0.05072 0.04114 = 0.04242 0.01930 0.01093 0.00696 C3 1 0.606071 0.165143 0.820243 11.00000 0.02720 0.04024 = 0.04806 0.02306 0.01249 0.00882 C4 1 0.510145 0.193075 0.695300 11.00000 0.02738 0.03844 = 0.03092 0.01338 0.00647 0.01086 C5 1 0.338844 0.183576 0.673977 11.00000 0.03829 0.04196 = 0.03741 0.01572 0.01004 0.01345 C6 1 0.336465 0.245717 0.472905 11.00000 0.04099 0.03344 = 0.04354 0.01237 0.00452 0.01097 C7 1 0.582420 0.237292 0.592334 11.00000 0.03389 0.02987 = 0.03608 0.01053 0.00461 0.00936 C8 1 0.818280 0.296636 0.494570 11.00000 0.04355 0.06605 = 0.04577 0.02959 0.01761 0.01219 AFIX 137 H8A 2 0.756996 0.212749 0.393029 11.00000 -1.50000 H8B 2 0.935323 0.295747 0.511586 11.00000 -1.50000 H8C 2 0.811115 0.408091 0.503669 11.00000 -1.50000 AFIX 0 C9 1 0.323250 0.302603 0.254006 11.00000 0.05905 0.05674 = 0.05243 0.03273 0.00736 0.02091 AFIX 137 H9A 2 0.243526 0.321521 0.182750 11.00000 -1.50000 H9B 2 0.362514 0.206772 0.198696 11.00000 -1.50000 H9C 2 0.418150 0.402996 0.306675 11.00000 -1.50000 AFIX 0 C10 1 0.085068 0.127584 0.747167 11.00000 0.02681 0.07237 = 0.06010 0.02468 0.01454 0.01304 AFIX 137 H10A 2 0.028240 0.039609 0.646203 11.00000 -1.50000 H10B 2 0.062522 0.233631 0.754800 11.00000 -1.50000 H10C 2 0.044196 0.095933 0.823534 11.00000 -1.50000 AFIX 0 PART 1 F6A 3 0.950486 0.312292 1.057199 21.00000 0.03504 0.13025 = 0.06745 0.04142 0.00447 0.01541 F7A 3 0.756251 0.174507 1.113321 21.00000 0.06622 0.06974 = 0.07621 0.04835 -0.00755 0.00480 PART 2 F6B 3 0.893707 0.201914 1.061823 -21.00000 0.05292 0.11352 = 0.09813 -0.00582 -0.03351 0.03351 F7B 3 0.679608 0.221180 1.143705 -21.00000 0.05184 0.11165 = 0.06717 0.06980 -0.00458 -0.01189 HKLF 4 REM mo_scan_a.res in P-1 REM R1 = 0.0649 for 1140 Fo > 4sig(Fo) and 0.1604 for all 2392 data REM 222 parameters refined using 0 restraints END WGHT 0.0543 0.0000 REM Highest difference peak 0.374, deepest hole -0.303, 1-sigma level 0.071 Q1 1 0.8605 0.3922 0.9073 11.00000 0.05 0.37 Q2 1 0.2538 0.1053 0.5244 11.00000 0.05 0.26 Q3 1 0.4825 0.3223 0.2763 11.00000 0.05 0.24 Q4 1 0.1344 0.1948 0.5610 11.00000 0.05 0.23 Q5 1 0.2785 0.0789 0.8401 11.00000 0.05 0.23 ; _shelx_res_checksum 20532 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 3.815 _oxdiff_exptl_absorpt_empirical_full_min 0.589 ####################################################################### # # 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_jk1286 _database_code_depnum_ccdc_archive 'CCDC 2180253' loop_ _audit_author_name _audit_author_address 'Serhii Vasylevskyi' ;OIST Okinawa Institute of Science and Technology Japan ; _audit_update_record ; 2022-06-20 deposited with the CCDC. 2022-10-14 downloaded from the CCDC. ; _audit_creation_date 2022-03-18 _audit_creation_method ; Olex2 1.5 (compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439) ; _shelx_SHELXL_version_number 2016/6 loop_ _audit_author_email serhii.vasylevskyi@oist.jp _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C9 H9 F5 N2 O3' _chemical_formula_sum 'C9 H9 F5 N2 O3' _chemical_formula_weight 288.18 _chemical_melting_point ? _chemical_oxdiff_formula C5H4O3F5N2 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' N N 0.0311 0.0180 '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' _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. ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9519(6) _cell_length_b 8.3267(6) _cell_length_c 9.1611(7) _cell_angle_alpha 82.449(6) _cell_angle_beta 72.420(7) _cell_angle_gamma 77.031(6) _cell_volume 562.18(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3768 _cell_measurement_temperature 100 _cell_measurement_theta_max 78.9680 _cell_measurement_theta_min 5.0840 _shelx_estimated_absorpt_T_max 0.876 _shelx_estimated_absorpt_T_min 0.815 _exptl_absorpt_coefficient_mu 1.623 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59899 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_F_000 292 _exptl_crystal_size_max 0.131 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.084 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_unetI/netI 0.0356 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.959 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7514 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.959 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.873 _diffrn_reflns_theta_min 5.076 _diffrn_ambient_temperature 100 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.8140 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.959 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 24.00 139.00 0.50 5.00 -- 49.60 38.00-120.00 230 2 \w 22.00 139.00 0.50 5.00 -- 49.60 57.00 -90.00 234 3 \w -40.00 85.00 0.50 5.00 -- 49.60 -82.00 90.00 250 4 \w -40.00 75.00 0.50 5.00 -- 49.60 -38.00 -30.00 230 5 \w -40.00 75.00 0.50 5.00 -- 49.60 -38.00 60.00 230 6 \w 21.00 146.00 0.50 50.00 -- 110.20 -82.00 30.00 250 7 \w 75.00 200.00 0.50 50.00 -- 110.20 82.00 60.00 250 8 \w 75.00 200.00 0.50 50.00 -- 110.20 82.00 -30.00 250 9 \w 21.00 146.00 0.50 50.00 -- 110.20 -82.00-180.00 250 10 \w 65.00 200.00 0.50 50.00 -- 110.20 15.00 30.00 270 11 \w 83.00 200.00 0.50 50.00 -- 110.20 30.00 -90.00 234 12 \w 21.00 139.00 0.50 50.00 -- 110.20 -61.00 30.00 236 13 \w 21.00 146.00 0.50 50.00 -- 110.20 -82.00 -30.00 250 14 \w 77.00 200.00 0.50 50.00 -- 110.20 77.00 90.00 246 15 \w 65.00 200.00 0.50 50.00 -- 110.20 15.00 0.00 270 16 \w 21.00 121.00 0.50 50.00 -- 110.20 -82.00 120.00 200 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa dual home/near' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1190836000 _diffrn_orient_matrix_UB_12 -0.1062615000 _diffrn_orient_matrix_UB_13 0.0958857000 _diffrn_orient_matrix_UB_21 0.1688392000 _diffrn_orient_matrix_UB_22 0.0144277000 _diffrn_orient_matrix_UB_23 -0.1347647000 _diffrn_orient_matrix_UB_31 0.0159576000 _diffrn_orient_matrix_UB_32 0.1572130000 _diffrn_orient_matrix_UB_33 0.0625207000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _diffrn_special_details ? _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2051 _reflns_number_total 2353 _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. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2016/6 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _refine_diff_density_max 0.307 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.076 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 2353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0438 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0887P)^2^+0.0766P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1281 _refine_ls_wR_factor_ref 0.1326 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.5 times of: All C(H,H,H) groups 2.a Idealised Me refined as rotating group: C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary ? 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 0.45496(13) 0.29688(12) 0.92404(11) 0.0245(2) Uani 1 1 d . . . . . O1 O 0.33270(16) 0.58722(13) 0.82141(12) 0.0214(3) Uani 1 1 d . . . . . N1 N 0.27490(17) 0.61575(16) 0.58863(14) 0.0203(3) Uani 1 1 d . . . . . C1 C 0.1876(2) 0.20421(19) 0.98329(17) 0.0219(3) Uani 1 1 d . . . . . F2 F 0.45325(13) 0.08379(11) 0.81190(10) 0.0244(2) Uani 1 1 d . . . . . O2 O 0.21923(16) 0.64253(14) 0.36153(12) 0.0228(3) Uani 1 1 d . . . . . N2 N 0.24691(17) 0.38123(17) 0.47905(14) 0.0206(3) Uani 1 1 d . . . . . C2 C 0.3568(2) 0.23469(19) 0.85530(17) 0.0199(3) Uani 1 1 d . . . . . F3 F 0.23099(15) 0.10372(14) 1.09782(11) 0.0347(3) Uani 1 1 d . . . . . O3 O 0.27713(16) 0.12553(14) 0.60625(12) 0.0242(3) Uani 1 1 d . . . . . C3 C 0.3180(2) 0.34557(18) 0.72092(16) 0.0187(3) Uani 1 1 d . . . . . F4 F 0.08977(14) 0.34601(13) 1.04021(11) 0.0283(3) Uani 1 1 d . . . . . C4 C 0.2805(2) 0.28511(19) 0.60034(16) 0.0191(3) Uani 1 1 d . . . . . F5 F 0.08495(14) 0.13435(12) 0.92954(11) 0.0274(3) Uani 1 1 d . . . . . C5 C 0.2192(2) 0.0707(2) 0.48930(19) 0.0264(4) Uani 1 1 d . . . . . H5A H 0.297733 0.097340 0.387836 0.040 Uiso 1 1 calc R U . . . H5B H 0.095028 0.126690 0.495928 0.040 Uiso 1 1 calc R U . . . H5C H 0.225554 -0.048935 0.504850 0.040 Uiso 1 1 calc R U . . . C6 C 0.2482(2) 0.54021(19) 0.48036(16) 0.0193(3) Uani 1 1 d . . . . . C7 C 0.1946(2) 0.5693(2) 0.23685(17) 0.0247(3) Uani 1 1 d . . . . . H7A H 0.172094 0.655840 0.157690 0.037 Uiso 1 1 calc R U . . . H7B H 0.091837 0.513685 0.275542 0.037 Uiso 1 1 calc R U . . . H7C H 0.303333 0.488750 0.192718 0.037 Uiso 1 1 calc R U . . . C8 C 0.3081(2) 0.51789(19) 0.70798(16) 0.0187(3) Uani 1 1 d . . . . . C9 C 0.3244(2) 0.7633(2) 0.80294(17) 0.0238(3) Uani 1 1 d . . . . . H9A H 0.418539 0.789786 0.711210 0.036 Uiso 1 1 calc R U . . . H9B H 0.342787 0.800026 0.893334 0.036 Uiso 1 1 calc R U . . . H9C H 0.206343 0.819650 0.791718 0.036 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 0.0301(5) 0.0238(5) 0.0248(4) 0.0028(4) -0.0154(4) -0.0076(4) O1 0.0313(6) 0.0173(6) 0.0185(5) 0.0004(4) -0.0105(4) -0.0068(4) N1 0.0240(6) 0.0197(6) 0.0172(6) 0.0021(5) -0.0066(5) -0.0053(5) C1 0.0289(8) 0.0184(7) 0.0187(7) 0.0047(6) -0.0092(6) -0.0052(6) F2 0.0282(5) 0.0176(5) 0.0261(5) -0.0010(4) -0.0095(4) 0.0005(4) O2 0.0306(6) 0.0220(6) 0.0173(5) 0.0037(4) -0.0102(4) -0.0065(4) N2 0.0236(7) 0.0210(7) 0.0174(6) 0.0006(5) -0.0059(5) -0.0055(5) C2 0.0237(7) 0.0181(7) 0.0194(6) -0.0009(5) -0.0088(6) -0.0038(5) F3 0.0372(6) 0.0384(6) 0.0245(5) 0.0153(4) -0.0119(4) -0.0050(5) O3 0.0353(7) 0.0187(6) 0.0218(5) 0.0000(4) -0.0114(5) -0.0078(5) C3 0.0215(7) 0.0182(7) 0.0166(6) 0.0004(5) -0.0058(5) -0.0046(5) F4 0.0305(5) 0.0263(5) 0.0247(5) -0.0036(4) -0.0037(4) -0.0030(4) C4 0.0206(7) 0.0196(7) 0.0170(6) -0.0002(5) -0.0050(5) -0.0045(5) F5 0.0300(5) 0.0258(5) 0.0286(5) 0.0020(4) -0.0082(4) -0.0126(4) C5 0.0359(9) 0.0229(8) 0.0245(7) -0.0027(6) -0.0117(6) -0.0091(6) C6 0.0195(7) 0.0211(7) 0.0169(6) 0.0019(6) -0.0055(5) -0.0048(5) C7 0.0291(8) 0.0296(8) 0.0178(7) 0.0015(6) -0.0100(6) -0.0075(6) C8 0.0203(7) 0.0200(7) 0.0167(6) 0.0000(5) -0.0057(5) -0.0058(5) C9 0.0333(8) 0.0187(7) 0.0219(7) 0.0003(6) -0.0099(6) -0.0081(6) _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 C2 1.3556(18) . ? O1 C8 1.3351(18) . ? O1 C9 1.4423(19) . ? N1 C6 1.332(2) . ? N1 C8 1.3314(19) . ? C1 C2 1.540(2) . ? C1 F3 1.3337(17) . ? C1 F4 1.3325(19) . ? C1 F5 1.3333(19) . ? F2 C2 1.3562(18) . ? O2 C6 1.3356(17) . ? O2 C7 1.4443(18) . ? N2 C4 1.3404(19) . ? N2 C6 1.328(2) . ? C2 C3 1.5054(19) . ? O3 C4 1.329(2) . ? O3 C5 1.4453(19) . ? C3 C4 1.405(2) . ? C3 C8 1.410(2) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 C8 O1 C9 116.86(12) . . ? C8 N1 C6 115.35(13) . . ? F3 C1 C2 111.20(13) . . ? F4 C1 C2 110.63(13) . . ? F4 C1 F3 108.32(12) . . ? F4 C1 F5 108.13(13) . . ? F5 C1 C2 110.79(13) . . ? F5 C1 F3 107.66(13) . . ? C6 O2 C7 116.69(12) . . ? C6 N2 C4 115.61(13) . . ? F1 C2 C1 105.70(12) . . ? F1 C2 F2 106.19(12) . . ? F1 C2 C3 112.12(12) . . ? F2 C2 C1 106.42(12) . . ? F2 C2 C3 111.69(12) . . ? C3 C2 C1 114.16(12) . . ? C4 O3 C5 117.47(12) . . ? C4 C3 C2 122.01(13) . . ? C4 C3 C8 114.39(13) . . ? C8 C3 C2 123.54(13) . . ? N2 C4 C3 123.06(14) . . ? O3 C4 N2 118.03(13) . . ? O3 C4 C3 118.91(13) . . ? O3 C5 H5A 109.5 . . ? O3 C5 H5B 109.5 . . ? O3 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 O2 113.25(13) . . ? N2 C6 N1 127.99(13) . . ? N2 C6 O2 118.76(13) . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C8 C3 118.47(13) . . ? N1 C8 O1 118.01(13) . . ? N1 C8 C3 123.52(14) . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 F1 C2 C3 C4 155.83(14) . . . . ? F1 C2 C3 C8 -27.1(2) . . . . ? C1 C2 C3 C4 -84.00(18) . . . . ? C1 C2 C3 C8 93.10(18) . . . . ? F2 C2 C3 C4 36.78(19) . . . . ? F2 C2 C3 C8 -146.11(14) . . . . ? C2 C3 C4 N2 -179.49(13) . . . . ? C2 C3 C4 O3 0.9(2) . . . . ? C2 C3 C8 O1 -0.7(2) . . . . ? C2 C3 C8 N1 179.55(14) . . . . ? F3 C1 C2 F1 -57.06(16) . . . . ? F3 C1 C2 F2 55.57(16) . . . . ? F3 C1 C2 C3 179.25(12) . . . . ? F4 C1 C2 F1 63.35(15) . . . . ? F4 C1 C2 F2 175.98(11) . . . . ? F4 C1 C2 C3 -60.34(17) . . . . ? C4 N2 C6 N1 -1.6(2) . . . . ? C4 N2 C6 O2 178.71(13) . . . . ? C4 C3 C8 O1 176.65(13) . . . . ? C4 C3 C8 N1 -3.2(2) . . . . ? F5 C1 C2 F1 -176.74(11) . . . . ? F5 C1 C2 F2 -64.11(15) . . . . ? F5 C1 C2 C3 59.56(17) . . . . ? C5 O3 C4 N2 -6.2(2) . . . . ? C5 O3 C4 C3 173.44(13) . . . . ? C6 N1 C8 O1 -178.82(13) . . . . ? C6 N1 C8 C3 1.0(2) . . . . ? C6 N2 C4 O3 178.63(13) . . . . ? C6 N2 C4 C3 -1.0(2) . . . . ? C7 O2 C6 N1 178.13(13) . . . . ? C7 O2 C6 N2 -2.1(2) . . . . ? C8 N1 C6 O2 -178.67(13) . . . . ? C8 N1 C6 N2 1.6(2) . . . . ? C8 C3 C4 N2 3.2(2) . . . . ? C8 C3 C4 O3 -176.49(13) . . . . ? C9 O1 C8 N1 -1.2(2) . . . . ? C9 O1 C8 C3 179.03(13) . . . . ? _shelx_res_file ; TITL jk1286_a.res in P-1 jk1286.res created by SHELXL-2016/6 at 09:37:42 on 18-Mar-2022 REM Old TITL JK1286 in P-1 REM SHELXT solution in P-1 REM R1 0.117, Rweak 0.003, Alpha 0.031, Orientation as input REM Formula found by SHELXT: C10 N O3 F5 CELL 1.54184 7.951892 8.326735 9.161084 82.4494 72.4199 77.0305 ZERR 2 0.000608 0.000561 0.000693 0.006 0.0068 0.0063 LATT 1 SFAC C H F N O UNIT 18 18 10 4 6 L.S. 20 PLAN 11 SIZE 0.084 0.12 0.131 TEMP -173.15 CONF BOND $H list 4 MORE -1 fmap 2 53 acta REM REM REM WGHT 0.088700 0.076600 FVAR 2.39664 F1 3 0.454961 0.296880 0.924043 11.00000 0.03009 0.02381 = 0.02475 0.00282 -0.01539 -0.00760 O1 5 0.332698 0.587224 0.821407 11.00000 0.03128 0.01729 = 0.01846 0.00042 -0.01053 -0.00680 N1 4 0.274901 0.615753 0.588627 11.00000 0.02404 0.01975 = 0.01719 0.00206 -0.00659 -0.00525 C1 1 0.187571 0.204208 0.983286 11.00000 0.02886 0.01842 = 0.01868 0.00468 -0.00921 -0.00525 F2 3 0.453247 0.083791 0.811904 11.00000 0.02819 0.01764 = 0.02609 -0.00096 -0.00946 0.00053 O2 5 0.219234 0.642529 0.361535 11.00000 0.03059 0.02205 = 0.01729 0.00370 -0.01016 -0.00653 N2 4 0.246913 0.381232 0.479048 11.00000 0.02356 0.02101 = 0.01737 0.00057 -0.00589 -0.00547 C2 1 0.356827 0.234686 0.855302 11.00000 0.02375 0.01806 = 0.01941 -0.00087 -0.00884 -0.00378 F3 3 0.230990 0.103716 1.097815 11.00000 0.03722 0.03839 = 0.02447 0.01526 -0.01193 -0.00503 O3 5 0.277134 0.125526 0.606248 11.00000 0.03530 0.01874 = 0.02183 -0.00002 -0.01144 -0.00779 C3 1 0.318001 0.345573 0.720920 11.00000 0.02153 0.01824 = 0.01661 0.00042 -0.00579 -0.00456 F4 3 0.089770 0.346013 1.040211 11.00000 0.03046 0.02629 = 0.02465 -0.00363 -0.00368 -0.00305 C4 1 0.280547 0.285110 0.600340 11.00000 0.02056 0.01955 = 0.01704 -0.00023 -0.00503 -0.00446 F5 3 0.084949 0.134347 0.929543 11.00000 0.02998 0.02585 = 0.02860 0.00202 -0.00818 -0.01261 C5 1 0.219199 0.070746 0.489303 11.00000 0.03591 0.02290 = 0.02449 -0.00273 -0.01169 -0.00905 AFIX 137 H5A 2 0.297733 0.097340 0.387836 11.00000 -1.50000 H5B 2 0.095028 0.126690 0.495928 11.00000 -1.50000 H5C 2 0.225554 -0.048935 0.504850 11.00000 -1.50000 AFIX 0 C6 1 0.248248 0.540207 0.480364 11.00000 0.01946 0.02114 = 0.01691 0.00187 -0.00547 -0.00483 C7 1 0.194648 0.569317 0.236851 11.00000 0.02910 0.02963 = 0.01777 0.00154 -0.01003 -0.00748 AFIX 137 H7A 2 0.172094 0.655840 0.157690 11.00000 -1.50000 H7B 2 0.091837 0.513685 0.275542 11.00000 -1.50000 H7C 2 0.303333 0.488750 0.192718 11.00000 -1.50000 AFIX 0 C8 1 0.308087 0.517892 0.707977 11.00000 0.02027 0.01995 = 0.01667 0.00001 -0.00574 -0.00580 C9 1 0.324429 0.763280 0.802937 11.00000 0.03335 0.01873 = 0.02190 0.00033 -0.00988 -0.00812 AFIX 137 H9A 2 0.418539 0.789786 0.711210 11.00000 -1.50000 H9B 2 0.342787 0.800026 0.893334 11.00000 -1.50000 H9C 2 0.206343 0.819650 0.791718 11.00000 -1.50000 AFIX 0 HKLF 4 REM jk1286_a.res in P-1 REM R1 = 0.0438 for 2051 Fo > 4sig(Fo) and 0.0492 for all 2353 data REM 175 parameters refined using 0 restraints END WGHT 0.0887 0.0766 REM Highest difference peak 0.307, deepest hole -0.365, 1-sigma level 0.076 Q1 1 0.5658 -0.0234 0.7780 11.00000 0.05 0.31 Q2 1 0.3455 0.4219 0.7074 11.00000 0.05 0.30 Q3 1 0.2386 0.4403 0.4798 11.00000 0.05 0.29 Q4 1 0.2468 0.7373 0.6061 11.00000 0.05 0.27 Q5 1 0.4408 -0.0286 0.7997 11.00000 0.05 0.26 Q6 1 0.1265 0.7517 0.3983 11.00000 0.05 0.25 Q7 1 0.4666 0.4125 0.9454 11.00000 0.05 0.24 Q8 1 0.0831 0.0191 0.9261 11.00000 0.05 0.24 Q9 1 0.1922 0.3973 1.0330 11.00000 0.05 0.24 Q10 1 0.2319 0.4350 0.7413 11.00000 0.05 0.24 Q11 1 0.2174 0.0255 0.8760 11.00000 0.05 0.23 ; _shelx_res_checksum 62273 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.397 _oxdiff_exptl_absorpt_empirical_full_min 0.774 ####################################################################### # # 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_mo_ds3_a _database_code_depnum_ccdc_archive 'CCDC 2180254' loop_ _audit_author_name _audit_author_address 'Serhii Vasylevskyi' ;OIST Okinawa Institute of Science and Technology Japan ; _audit_update_record ; 2022-06-20 deposited with the CCDC. 2022-10-14 downloaded from the CCDC. ; _audit_creation_date 2022-03-18 _audit_creation_method ; Olex2 1.5 (compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439) ; _shelx_SHELXL_version_number 2016/6 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C11 H8 F5 N' _chemical_formula_sum 'C11 H8 F5 N' _chemical_formula_weight 249.18 _chemical_melting_point ? _chemical_oxdiff_formula 'C11 H10 N O' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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. ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.8320(7) _cell_length_b 6.1313(5) _cell_length_c 22.4930(17) _cell_angle_alpha 90 _cell_angle_beta 93.678(7) _cell_angle_gamma 90 _cell_volume 1077.90(15) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1344 _cell_measurement_temperature 200.00(10) _cell_measurement_theta_max 21.9990 _cell_measurement_theta_min 3.6170 _shelx_estimated_absorpt_T_max 0.966 _shelx_estimated_absorpt_T_min 0.962 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.09338 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0797 _diffrn_reflns_av_unetI/netI 0.0600 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 9790 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.020 _diffrn_reflns_theta_min 3.445 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 200.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \f -60.46 169.54 1.00 15.00 5.96 -1.62 -31.50 -- 230 2 \w -85.28 18.72 1.00 15.00 -- -1.62 -59.25 20.08 104 3 \w -85.28 18.72 1.00 15.00 -- -1.62 -59.25 92.08 104 4 \w -85.28 18.72 1.00 15.00 -- -1.62 -59.25-123.92 104 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'Saxi-CrysAlisPro-abstract goniometer imported SAXI images' _diffrn_measurement_method '\w and \f scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0091482000 _diffrn_orient_matrix_UB_12 0.0942843000 _diffrn_orient_matrix_UB_13 0.0177892000 _diffrn_orient_matrix_UB_21 0.0003667000 _diffrn_orient_matrix_UB_22 0.0664741000 _diffrn_orient_matrix_UB_23 -0.0258017000 _diffrn_orient_matrix_UB_31 -0.0902806000 _diffrn_orient_matrix_UB_32 -0.0093323000 _diffrn_orient_matrix_UB_33 -0.0039466000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1458 _reflns_number_total 2111 _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. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2016/6 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _refine_diff_density_max 0.217 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef 0.024(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 2111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0566 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.0148P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1280 _refine_ls_wR_factor_ref 0.1490 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C8(H8), C9(H9) 2.b Idealised Me refined as rotating group: C11(H11a,H11b,H11c) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary ? _atom_sites_solution_secondary ? 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 0.2776(2) 1.0488(3) 0.57142(7) 0.0666(6) Uani 1 1 d . . . . . F2 F 0.0401(2) 0.7273(3) 0.57906(8) 0.0740(6) Uani 1 1 d . . . . . F3 F 0.1183(3) 0.7877(3) 0.49083(8) 0.0774(6) Uani 1 1 d . . . . . F4 F 0.2054(2) 0.5013(3) 0.53832(8) 0.0698(6) Uani 1 1 d . . . . . F5 F 0.4477(2) 0.8146(3) 0.53186(7) 0.0678(6) Uani 1 1 d . . . . . N1 N 0.3421(3) 0.8785(4) 0.68142(9) 0.0424(6) Uani 1 1 d . . . . . H1 H 0.275(4) 0.990(5) 0.6805(13) 0.062(10) Uiso 1 1 d . . . . . C1 C 0.1697(4) 0.7111(5) 0.54442(13) 0.0532(8) Uani 1 1 d . . . . . C2 C 0.3254(4) 0.8347(4) 0.57105(12) 0.0473(7) Uani 1 1 d . . . . . C3 C 0.3902(3) 0.7657(4) 0.63152(11) 0.0389(6) Uani 1 1 d . . . . . C4 C 0.4969(3) 0.5976(4) 0.64817(11) 0.0389(6) Uani 1 1 d . . . . . C5 C 0.5159(3) 0.6062(4) 0.71242(12) 0.0405(6) Uani 1 1 d . . . . . C6 C 0.6084(3) 0.4782(4) 0.75488(13) 0.0460(7) Uani 1 1 d . . . . . H6 H 0.673986 0.357084 0.743126 0.055 Uiso 1 1 calc R U . . . C7 C 0.6018(3) 0.5327(5) 0.81412(13) 0.0509(7) Uani 1 1 d . . . . . H7 H 0.663245 0.446827 0.843432 0.061 Uiso 1 1 calc R U . . . C8 C 0.5069(3) 0.7109(5) 0.83209(13) 0.0492(7) Uani 1 1 d . . . . . H8 H 0.506368 0.744512 0.873308 0.059 Uiso 1 1 calc R U . . . C9 C 0.4135(3) 0.8400(5) 0.79118(12) 0.0473(7) Uani 1 1 d . . . . . H9 H 0.348673 0.961183 0.803303 0.057 Uiso 1 1 calc R U . . . C10 C 0.4195(3) 0.7829(4) 0.73128(11) 0.0379(6) Uani 1 1 d . . . . . C11 C 0.5829(4) 0.4363(5) 0.60974(14) 0.0588(8) Uani 1 1 d . . . . . H11A H 0.703496 0.476234 0.607602 0.088 Uiso 1 1 calc R U . . . H11B H 0.526326 0.437367 0.569589 0.088 Uiso 1 1 calc R U . . . H11C H 0.574969 0.290086 0.626930 0.088 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 0.1013(14) 0.0373(10) 0.0593(12) 0.0075(8) -0.0099(10) 0.0037(9) F2 0.0570(11) 0.1006(16) 0.0637(12) -0.0110(11) -0.0011(9) -0.0049(10) F3 0.1021(15) 0.0805(14) 0.0459(11) 0.0030(9) -0.0246(10) 0.0108(11) F4 0.0878(13) 0.0477(11) 0.0711(13) -0.0102(9) -0.0169(10) -0.0028(9) F5 0.0791(12) 0.0793(14) 0.0467(10) 0.0095(9) 0.0184(9) -0.0085(10) N1 0.0481(13) 0.0401(14) 0.0385(13) -0.0014(10) -0.0009(10) 0.0076(10) C1 0.0693(19) 0.0517(19) 0.0375(16) -0.0038(13) -0.0043(14) 0.0043(15) C2 0.0671(18) 0.0380(16) 0.0372(15) 0.0043(11) 0.0068(13) 0.0032(13) C3 0.0419(14) 0.0368(14) 0.0381(14) -0.0023(11) 0.0034(10) -0.0020(11) C4 0.0379(13) 0.0399(15) 0.0391(15) -0.0023(11) 0.0039(10) -0.0013(11) C5 0.0333(13) 0.0420(15) 0.0459(15) -0.0007(12) -0.0005(10) -0.0031(10) C6 0.0389(14) 0.0453(16) 0.0529(17) 0.0031(13) -0.0031(11) 0.0021(11) C7 0.0421(15) 0.0592(19) 0.0500(18) 0.0088(14) -0.0080(12) -0.0060(13) C8 0.0449(15) 0.064(2) 0.0378(15) -0.0001(13) -0.0018(11) -0.0069(13) C9 0.0436(14) 0.0560(18) 0.0422(16) -0.0080(13) 0.0023(11) 0.0022(12) C10 0.0351(12) 0.0396(15) 0.0385(14) -0.0020(11) -0.0014(10) -0.0017(10) C11 0.0580(17) 0.062(2) 0.0559(19) -0.0147(15) 0.0001(14) 0.0137(14) _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 C2 1.365(3) . ? F2 C1 1.322(3) . ? F3 C1 1.332(3) . ? F4 C1 1.325(3) . ? F5 C2 1.348(3) . ? N1 H1 0.86(3) . ? N1 C3 1.391(3) . ? N1 C10 1.372(3) . ? C1 C2 1.525(4) . ? C2 C3 1.483(4) . ? C3 C4 1.364(3) . ? C4 C5 1.444(3) . ? C4 C11 1.501(4) . ? C5 C6 1.402(4) . ? C5 C10 1.401(3) . ? C6 H6 0.9500 . ? C6 C7 1.378(4) . ? C7 H7 0.9500 . ? C7 C8 1.396(4) . ? C8 H8 0.9500 . ? C8 C9 1.386(4) . ? C9 H9 0.9500 . ? C9 C10 1.396(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 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 C3 N1 H1 125(2) . . ? C10 N1 H1 127(2) . . ? C10 N1 C3 108.6(2) . . ? F2 C1 F3 107.9(2) . . ? F2 C1 F4 108.0(3) . . ? F2 C1 C2 110.8(2) . . ? F3 C1 C2 111.6(3) . . ? F4 C1 F3 107.6(2) . . ? F4 C1 C2 110.7(2) . . ? F1 C2 C1 105.5(2) . . ? F1 C2 C3 110.3(2) . . ? F5 C2 F1 107.4(2) . . ? F5 C2 C1 106.3(2) . . ? F5 C2 C3 111.0(2) . . ? C3 C2 C1 115.9(2) . . ? N1 C3 C2 120.2(2) . . ? C4 C3 N1 110.3(2) . . ? C4 C3 C2 129.4(2) . . ? C3 C4 C5 105.6(2) . . ? C3 C4 C11 129.0(2) . . ? C5 C4 C11 125.4(2) . . ? C6 C5 C4 132.6(3) . . ? C10 C5 C4 107.9(2) . . ? C10 C5 C6 119.4(2) . . ? C5 C6 H6 120.9 . . ? C7 C6 C5 118.3(3) . . ? C7 C6 H6 120.9 . . ? C6 C7 H7 119.2 . . ? C6 C7 C8 121.6(3) . . ? C8 C7 H7 119.2 . . ? C7 C8 H8 119.2 . . ? C9 C8 C7 121.5(3) . . ? C9 C8 H8 119.2 . . ? C8 C9 H9 121.7 . . ? C8 C9 C10 116.6(3) . . ? C10 C9 H9 121.7 . . ? N1 C10 C5 107.6(2) . . ? N1 C10 C9 129.9(2) . . ? C9 C10 C5 122.6(2) . . ? C4 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? C4 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 F1 C2 C3 N1 22.9(4) . . . . ? F1 C2 C3 C4 -157.3(3) . . . . ? F2 C1 C2 F1 -64.2(3) . . . . ? F2 C1 C2 F5 -178.0(2) . . . . ? F2 C1 C2 C3 58.1(3) . . . . ? F3 C1 C2 F1 56.1(3) . . . . ? F3 C1 C2 F5 -57.7(3) . . . . ? F3 C1 C2 C3 178.5(2) . . . . ? F4 C1 C2 F1 176.0(2) . . . . ? F4 C1 C2 F5 62.1(3) . . . . ? F4 C1 C2 C3 -61.7(3) . . . . ? F5 C2 C3 N1 141.7(2) . . . . ? F5 C2 C3 C4 -38.4(4) . . . . ? N1 C3 C4 C5 0.1(3) . . . . ? N1 C3 C4 C11 -178.6(3) . . . . ? C1 C2 C3 N1 -96.9(3) . . . . ? C1 C2 C3 C4 83.0(4) . . . . ? C2 C3 C4 C5 -179.7(3) . . . . ? C2 C3 C4 C11 1.5(5) . . . . ? C3 N1 C10 C5 -0.7(3) . . . . ? C3 N1 C10 C9 178.5(3) . . . . ? C3 C4 C5 C6 -180.0(3) . . . . ? C3 C4 C5 C10 -0.5(3) . . . . ? C4 C5 C6 C7 179.0(3) . . . . ? C4 C5 C10 N1 0.7(3) . . . . ? C4 C5 C10 C9 -178.5(2) . . . . ? C5 C6 C7 C8 -0.4(4) . . . . ? C6 C5 C10 N1 -179.7(2) . . . . ? C6 C5 C10 C9 1.1(4) . . . . ? C6 C7 C8 C9 0.7(4) . . . . ? C7 C8 C9 C10 -0.1(4) . . . . ? C8 C9 C10 N1 -179.8(3) . . . . ? C8 C9 C10 C5 -0.7(4) . . . . ? C10 N1 C3 C2 -179.8(2) . . . . ? C10 N1 C3 C4 0.4(3) . . . . ? C10 C5 C6 C7 -0.5(4) . . . . ? C11 C4 C5 C6 -1.2(5) . . . . ? C11 C4 C5 C10 178.3(3) . . . . ? _shelx_res_file ; TITL mo_ds3_autored_a.res in P2(1)/n mo_ds3_a.res created by SHELXL-2016/6 at 17:35:24 on 16-Mar-2022 REM Old TITL mo_ds3_autored in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.216, Rweak 0.172, Alpha 0.040 REM 0.635 for 202 systematic absences, Orientation as input REM Formula found by SHELXT: C11 N O5 CELL 0.71073 7.832 6.1313 22.493 90 93.678 90 ZERR 4 0.0007 0.0005 0.0017 0 0.007 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H F N UNIT 44 32 20 4 L.S. 4 0 0 PLAN 5 SIZE 0.25 0.26 0.23 TEMP -73 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta OMIT 0 0 2 REM REM REM WGHT 0.059900 0.014800 EXTI 0.024041 FVAR 0.96837 F1 3 0.277571 1.048781 0.571424 11.00000 0.10130 0.03727 = 0.05928 0.00747 -0.00986 0.00373 F2 3 0.040142 0.727301 0.579058 11.00000 0.05698 0.10057 = 0.06368 -0.01096 -0.00112 -0.00488 F3 3 0.118306 0.787710 0.490829 11.00000 0.10206 0.08050 = 0.04595 0.00302 -0.02461 0.01076 F4 3 0.205412 0.501344 0.538315 11.00000 0.08777 0.04770 = 0.07105 -0.01019 -0.01685 -0.00285 F5 3 0.447688 0.814609 0.531862 11.00000 0.07912 0.07932 = 0.04666 0.00950 0.01836 -0.00854 N1 4 0.342065 0.878500 0.681424 11.00000 0.04813 0.04008 = 0.03854 -0.00139 -0.00093 0.00763 H1 2 0.275322 0.989529 0.680536 11.00000 0.06206 C1 1 0.169714 0.711056 0.544418 11.00000 0.06926 0.05172 = 0.03754 -0.00385 -0.00431 0.00430 C2 1 0.325405 0.834674 0.571048 11.00000 0.06705 0.03801 = 0.03719 0.00425 0.00676 0.00323 C3 1 0.390228 0.765672 0.631525 11.00000 0.04192 0.03683 = 0.03811 -0.00226 0.00339 -0.00204 C4 1 0.496868 0.597589 0.648167 11.00000 0.03787 0.03985 = 0.03911 -0.00228 0.00395 -0.00132 C5 1 0.515935 0.606227 0.712417 11.00000 0.03326 0.04203 = 0.04588 -0.00066 -0.00047 -0.00306 C6 1 0.608431 0.478214 0.754880 11.00000 0.03894 0.04528 = 0.05287 0.00313 -0.00306 0.00206 AFIX 43 H6 2 0.673986 0.357084 0.743126 11.00000 -1.20000 AFIX 0 C7 1 0.601792 0.532652 0.814121 11.00000 0.04213 0.05916 = 0.04996 0.00877 -0.00801 -0.00597 AFIX 43 H7 2 0.663245 0.446827 0.843432 11.00000 -1.20000 AFIX 0 C8 1 0.506936 0.710876 0.832093 11.00000 0.04491 0.06438 = 0.03784 -0.00006 -0.00182 -0.00690 AFIX 43 H8 2 0.506368 0.744512 0.873308 11.00000 -1.20000 AFIX 0 C9 1 0.413518 0.839961 0.791178 11.00000 0.04359 0.05595 = 0.04222 -0.00796 0.00230 0.00223 AFIX 43 H9 2 0.348673 0.961183 0.803303 11.00000 -1.20000 AFIX 0 C10 1 0.419533 0.782854 0.731275 11.00000 0.03506 0.03956 = 0.03849 -0.00196 -0.00140 -0.00169 C11 1 0.582879 0.436323 0.609737 11.00000 0.05803 0.06200 = 0.05592 -0.01465 0.00009 0.01370 AFIX 137 H11A 2 0.703496 0.476234 0.607602 11.00000 -1.50000 H11B 2 0.526326 0.437367 0.569589 11.00000 -1.50000 H11C 2 0.574969 0.290086 0.626930 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_ds3_autored_a.res in P2(1)/n REM R1 = 0.0566 for 1458 Fo > 4sig(Fo) and 0.0867 for all 2111 data REM 160 parameters refined using 0 restraints END WGHT 0.0599 0.0148 REM Highest difference peak 0.217, deepest hole -0.215, 1-sigma level 0.048 Q1 1 0.3920 0.6283 0.6366 11.00000 0.05 0.22 Q2 1 0.5235 0.6103 0.6794 11.00000 0.05 0.21 Q3 1 0.4104 1.0426 0.6208 11.00000 0.05 0.19 Q4 1 0.5203 0.5372 0.7172 11.00000 0.05 0.17 Q5 1 0.4190 0.8330 0.7601 11.00000 0.05 0.17 ; _shelx_res_checksum 65854 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 3.984 _oxdiff_exptl_absorpt_empirical_full_min 0.533 ####################################################################### # # 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_jk1392a _database_code_depnum_ccdc_archive 'CCDC 2180257' loop_ _audit_author_name _audit_author_address 'Serhii Vasylevskyi' ;OIST Okinawa Institute of Science and Technology Japan ; _audit_update_record ; 2022-06-20 deposited with the CCDC. 2022-10-14 downloaded from the CCDC. ; _audit_creation_date 2022-04-20 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _shelx_SHELXL_version_number 2014/7 loop_ _audit_author_email serhii.vasylevskyi@oist.jp _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C20 H18 F5 N O5' _chemical_formula_sum 'C20 H18 F5 N O5' _chemical_formula_weight 447.35 _chemical_absolute_configuration rm _chemical_melting_point ? _chemical_oxdiff_formula 'C10 H10 F5' 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' N N 0.0311 0.0180 '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' _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. ; _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_H-M_alt 'I 1 2 1' _space_group_name_Hall 'I 2y' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 20.3374(7) _cell_length_b 7.1756(3) _cell_length_c 14.0098(7) _cell_angle_alpha 90 _cell_angle_beta 92.999(4) _cell_angle_gamma 90 _cell_volume 2041.69(15) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5142 _cell_measurement_temperature 100 _cell_measurement_theta_max 78.3460 _cell_measurement_theta_min 3.7280 _shelx_estimated_absorpt_T_max 0.983 _shelx_estimated_absorpt_T_min 0.872 _exptl_absorpt_coefficient_mu 1.174 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83998 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_F_000 920 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.085 _exptl_crystal_size_min 0.015 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_unetI/netI 0.0387 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.978 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 11116 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 80.509 _diffrn_reflns_theta_min 3.742 _diffrn_ambient_temperature 100 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.8140 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -40.00 53.00 1.00 29.74 -- 49.60 -82.00-180.00 93 2 \w -36.00 69.00 1.00 29.74 -- 49.60 -19.00 -90.00 105 3 \w 26.00 80.00 1.00 29.74 -- 49.60 37.00 -90.00 54 4 \w -39.00 41.00 1.00 29.74 -- 49.60 -57.00 60.00 80 5 \w 86.00 138.00 1.00 29.74 -- 49.60 37.00 -90.00 52 6 \w 49.00 76.00 1.00 29.74 -- 49.60 37.00 -60.00 27 7 \w 58.00 111.00 1.00 29.74 -- 49.60 37.00-180.00 53 8 \w 93.00 135.00 1.00 118.94 -- 110.20 77.00 -30.00 42 9 \w 125.00 152.00 1.00 118.94 -- 110.20 82.00 150.00 27 10 \w 170.00 198.00 1.00 118.94 -- 110.20 61.00-120.00 28 11 \w 83.00 166.00 1.00 118.94 -- 110.20 61.00-120.00 83 12 \w 131.00 197.00 1.00 118.94 -- 110.20 30.00 90.00 66 13 \w 114.00 192.00 1.00 118.94 -- 110.20 15.00 -60.00 78 14 \w 132.00 199.00 1.00 118.94 -- 110.20 45.00 150.00 67 15 \w 22.00 138.00 1.00 118.94 -- 110.20 -61.00 60.00 116 16 \w 83.00 198.00 1.00 118.94 -- 110.20 30.00 -30.00 115 17 \w 133.00 166.00 1.00 118.94 -- 110.20 45.00-180.00 33 18 \w 71.00 96.00 1.00 118.94 -- 110.20 15.00 -60.00 25 19 \w 88.00 126.00 1.00 118.94 -- 110.20 45.00-180.00 38 20 \w 110.00 199.00 1.00 118.94 -- 110.20 45.00 120.00 89 21 \w 22.00 142.00 1.00 118.94 -- 110.20 -82.00 60.00 120 22 \w 78.00 104.00 1.00 118.94 -- 110.20 82.00 150.00 26 23 \w 89.00 117.00 1.00 118.94 -- 110.20 45.00 150.00 28 24 \w 83.00 160.00 1.00 118.94 -- 110.20 61.00-150.00 77 25 \w 31.00 56.00 1.00 118.94 -- 110.20 -45.00 60.00 25 26 \w 96.00 130.00 1.00 118.94 -- 110.20 30.00 120.00 34 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa dual home/near' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0540096000 _diffrn_orient_matrix_UB_12 0.1203210000 _diffrn_orient_matrix_UB_13 0.0422544000 _diffrn_orient_matrix_UB_21 -0.0037689000 _diffrn_orient_matrix_UB_22 -0.1371867000 _diffrn_orient_matrix_UB_23 0.0838097000 _diffrn_orient_matrix_UB_31 0.0531317000 _diffrn_orient_matrix_UB_32 0.1134748000 _diffrn_orient_matrix_UB_33 0.0574026000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _reflns_Friedel_coverage 0.815 _reflns_Friedel_fraction_full 0.992 _reflns_Friedel_fraction_max 0.939 _reflns_number_gt 3939 _reflns_number_total 4292 _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 71.98 _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. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2014/7 (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _refine_diff_density_max 0.418 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.057 _refine_ls_abs_structure_details ; Flack x determined using 1632 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.25(10) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 353 _refine_ls_number_reflns 4292 _refine_ls_number_restraints 251 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0567 _refine_ls_restrained_S_all 1.174 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+2.3568P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1515 _refine_ls_wR_factor_ref 0.1549 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C20B-C19B 1.5 with sigma of 0.02 F2B-C20B \\sim F2B-F1B \\sim C20B-F1B with sigma of 0.04 C19B-C5 \\sim C19B-F2B \\sim C19B-C20B \\sim C19B-F1B with sigma of 0.02 F5B-F4B \\sim F5B-F3B \\sim F4B-F3B with sigma of 0.04 C20B-F5B \\sim C20B-F4B \\sim C20B-C19B \\sim C20B-F3B with sigma of 0.02 3. Uiso/Uaniso restraints and constraints F1A \\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim C19A \\sim C20A \\sim F1B \\sim F2B \\sim F3B \\sim F4B \\sim F5B \\sim C19B \\sim C20B: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004 within 2A 4. Others Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(C19B)=Sof(C20B)=1-FVAR(1) Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(C19A)=Sof(C20A)=FVAR(1) 5.a Ternary CH refined with riding coordinates: C1(H1b) 5.b Secondary CH2 refined with riding coordinates: C2(H2a,H2b), C12(H12a,H12b) 5.c Aromatic/amide H refined with riding coordinates: C4(H4), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18) 5.d Idealised Me refined as rotating group: C10(H10a,H10b,H10c) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary ? 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 O1 O 0.23398(14) 0.2974(5) 0.0744(2) 0.0429(7) Uani 1 1 d . . . . . H1 H 0.192(3) 0.299(10) 0.073(4) 0.062(17) Uiso 1 1 d . . . . . O2 O 0.35997(15) 0.4001(5) 0.6624(2) 0.0445(7) Uani 1 1 d . . . . . O3 O 0.45518(12) 0.2853(4) 0.6144(2) 0.0376(6) Uani 1 1 d . . . . . O4 O 0.39835(12) 0.7833(4) 0.4287(2) 0.0371(6) Uani 1 1 d . . . . . O5 O 0.49286(12) 0.6781(4) 0.3704(2) 0.0368(6) Uani 1 1 d . . . . . N1 N 0.42881(15) 0.4775(5) 0.4408(2) 0.0341(7) Uani 1 1 d . . . . . H1A H 0.457(2) 0.394(7) 0.431(3) 0.031(11) Uiso 1 1 d . . . . . C1 C 0.37608(18) 0.4083(6) 0.4966(3) 0.0336(8) Uani 1 1 d . . . . . H1B H 0.3410 0.5055 0.4998 0.040 Uiso 1 1 calc R . . . . C2 C 0.34657(19) 0.2300(6) 0.4525(3) 0.0369(8) Uani 1 1 d . . . . . H2A H 0.3815 0.1340 0.4518 0.044 Uiso 1 1 calc R . . . . H2B H 0.3121 0.1836 0.4938 0.044 Uiso 1 1 calc R . . . . C3 C 0.31680(18) 0.2528(5) 0.3522(3) 0.0341(8) Uani 1 1 d . . . . . C4 C 0.35535(19) 0.2450(6) 0.2739(3) 0.0386(9) Uani 1 1 d . . . . . H4 H 0.4016 0.2301 0.2840 0.046 Uiso 1 1 calc R . . . . C5 C 0.32853(19) 0.2582(6) 0.1809(3) 0.0390(9) Uani 1 1 d D . . . . C6 C 0.26003(17) 0.2853(6) 0.1649(3) 0.0357(8) Uani 1 1 d . . . . . C7 C 0.22134(17) 0.2954(6) 0.2441(3) 0.0363(8) Uani 1 1 d . . . . . H7 H 0.1752 0.3132 0.2350 0.044 Uiso 1 1 calc R . . . . C8 C 0.24935(17) 0.2800(6) 0.3351(3) 0.0361(8) Uani 1 1 d . . . . . H8 H 0.2220 0.2880 0.3879 0.043 Uiso 1 1 calc R . . . . C9 C 0.40228(18) 0.3599(6) 0.5968(3) 0.0359(8) Uani 1 1 d . . . . . C10 C 0.3823(3) 0.3602(9) 0.7625(4) 0.0582(12) Uani 1 1 d . . . . . H10A H 0.3819 0.2253 0.7733 0.087 Uiso 1 1 calc GR . . . . H10B H 0.3527 0.4209 0.8059 0.087 Uiso 1 1 calc GR . . . . H10C H 0.4271 0.4081 0.7746 0.087 Uiso 1 1 calc GR . . . . C11 C 0.43647(17) 0.6544(6) 0.4156(3) 0.0326(8) Uani 1 1 d . . . . . C12 C 0.5055(2) 0.8668(7) 0.3376(4) 0.0475(11) Uani 1 1 d . . . . . H12A H 0.5105 0.9531 0.3926 0.057 Uiso 1 1 calc R . . . . H12B H 0.4685 0.9108 0.2946 0.057 Uiso 1 1 calc R . . . . C13 C 0.5679(2) 0.8597(6) 0.2851(3) 0.0420(9) Uani 1 1 d . . . . . C14 C 0.6283(2) 0.8691(7) 0.3376(4) 0.0496(10) Uani 1 1 d . . . . . H14 H 0.6295 0.8782 0.4053 0.060 Uiso 1 1 calc R . . . . C15 C 0.6861(3) 0.8650(9) 0.2902(6) 0.0744(19) Uani 1 1 d . . . . . H15 H 0.7271 0.8697 0.3257 0.089 Uiso 1 1 calc R . . . . C16 C 0.6850(4) 0.8543(10) 0.1930(7) 0.089(2) Uani 1 1 d . . . . . H16 H 0.7251 0.8521 0.1612 0.106 Uiso 1 1 calc R . . . . C17 C 0.6245(4) 0.8464(10) 0.1399(5) 0.085(2) Uani 1 1 d . . . . . H17 H 0.6235 0.8391 0.0722 0.102 Uiso 1 1 calc R . . . . C18 C 0.5659(3) 0.8493(8) 0.1874(4) 0.0587(13) Uani 1 1 d . . . . . H18 H 0.5248 0.8442 0.1520 0.070 Uiso 1 1 calc R . . . . F1A F 0.3472(2) 0.1310(6) 0.0280(3) 0.0593(8) Uani 0.872(4) 1 d . U P A 1 F2A F 0.43123(16) 0.1606(6) 0.1290(3) 0.0627(8) Uani 0.872(4) 1 d . U P A 1 F3A F 0.43142(18) 0.3979(8) -0.0171(3) 0.0749(10) Uani 0.872(4) 1 d . U P A 1 F4A F 0.4223(2) 0.5332(7) 0.1180(3) 0.0786(10) Uani 0.872(4) 1 d . U P A 1 F5A F 0.3387(2) 0.5133(6) 0.0174(3) 0.0639(10) Uani 0.872(4) 1 d . U P A 1 C19A C 0.3729(3) 0.2399(11) 0.0987(5) 0.0572(9) Uani 0.872(4) 1 d . U P A 1 C20A C 0.3920(3) 0.4215(12) 0.0535(5) 0.0621(9) Uani 0.872(4) 1 d . U P A 1 F1B F 0.3666(16) 0.462(4) 0.039(2) 0.0660(15) Uani 0.128(4) 1 d D U P A 2 F2B F 0.4398(10) 0.359(4) 0.1314(17) 0.0648(16) Uani 0.128(4) 1 d D U P A 2 F3B F 0.3227(12) 0.102(4) -0.0029(19) 0.059(2) Uani 0.128(4) 1 d D U P A 2 F4B F 0.4050(11) 0.015(4) 0.0976(17) 0.0613(17) Uani 0.128(4) 1 d D U P A 2 F5B F 0.4266(11) 0.185(4) -0.0337(17) 0.0667(19) Uani 0.128(4) 1 d D U P A 2 C19B C 0.3725(12) 0.309(4) 0.1059(17) 0.0618(11) Uani 0.128(4) 1 d D U P A 2 C20B C 0.3826(12) 0.163(4) 0.0381(17) 0.0607(11) Uani 0.128(4) 1 d D U P A 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 O1 0.0300(13) 0.0579(19) 0.0410(15) -0.0030(14) 0.0032(11) 0.0008(13) O2 0.0375(15) 0.0540(18) 0.0433(16) 0.0012(13) 0.0133(12) 0.0046(13) O3 0.0286(12) 0.0405(14) 0.0441(14) 0.0029(12) 0.0060(10) -0.0008(12) O4 0.0286(12) 0.0351(14) 0.0479(15) 0.0052(12) 0.0055(10) 0.0018(11) O5 0.0258(12) 0.0378(15) 0.0477(15) 0.0057(12) 0.0107(11) -0.0023(11) N1 0.0242(15) 0.0339(16) 0.0447(18) 0.0001(13) 0.0071(13) 0.0016(13) C1 0.0249(16) 0.0337(18) 0.043(2) 0.0015(15) 0.0077(14) 0.0002(14) C2 0.0293(17) 0.037(2) 0.044(2) 0.0034(16) 0.0039(15) -0.0020(14) C3 0.0278(16) 0.0294(19) 0.045(2) 0.0013(15) 0.0025(14) -0.0013(14) C4 0.0265(16) 0.042(2) 0.048(2) -0.0009(17) 0.0052(15) 0.0030(15) C5 0.0289(17) 0.045(2) 0.043(2) -0.0027(17) 0.0087(15) 0.0006(17) C6 0.0277(16) 0.0348(19) 0.045(2) -0.0015(17) 0.0038(14) 0.0004(16) C7 0.0235(15) 0.0337(19) 0.052(2) -0.0020(17) 0.0043(14) -0.0017(15) C8 0.0272(16) 0.0357(19) 0.046(2) 0.0001(17) 0.0097(14) -0.0038(15) C9 0.0283(17) 0.0358(19) 0.045(2) 0.0002(16) 0.0112(15) -0.0049(15) C10 0.059(3) 0.068(3) 0.049(3) -0.004(2) 0.013(2) 0.000(3) C11 0.0242(16) 0.040(2) 0.0336(17) -0.0012(15) 0.0026(13) -0.0034(15) C12 0.038(2) 0.040(2) 0.066(3) 0.013(2) 0.018(2) 0.0008(18) C13 0.041(2) 0.035(2) 0.052(2) 0.0044(17) 0.0173(18) -0.0035(17) C14 0.042(2) 0.045(2) 0.062(3) 0.001(2) 0.009(2) 0.001(2) C15 0.044(3) 0.053(3) 0.128(6) -0.002(3) 0.028(3) -0.004(2) C16 0.080(4) 0.068(4) 0.126(6) -0.010(4) 0.072(5) -0.014(4) C17 0.130(6) 0.061(4) 0.071(4) -0.013(3) 0.064(4) -0.021(4) C18 0.073(3) 0.051(3) 0.053(3) -0.001(2) 0.013(2) -0.016(3) F1A 0.0477(17) 0.0778(19) 0.0529(17) -0.0134(15) 0.0095(14) 0.0115(15) F2A 0.0395(14) 0.091(2) 0.0582(16) -0.0002(16) 0.0129(12) 0.0190(15) F3A 0.0517(17) 0.112(3) 0.0636(19) 0.0112(19) 0.0311(15) 0.0043(18) F4A 0.0639(19) 0.098(2) 0.075(2) 0.0009(19) 0.0186(17) -0.0295(18) F5A 0.0516(19) 0.072(2) 0.070(2) 0.0178(17) 0.0255(16) 0.0046(17) C19A 0.0379(15) 0.0811(19) 0.0537(16) -0.0041(16) 0.0139(14) 0.0072(16) C20A 0.0436(16) 0.085(2) 0.0586(17) -0.0001(16) 0.0173(15) 0.0009(16) F1B 0.048(3) 0.089(3) 0.063(3) 0.005(3) 0.021(2) -0.003(3) F2B 0.045(3) 0.090(3) 0.061(3) -0.001(3) 0.016(3) -0.001(3) F3B 0.042(4) 0.081(4) 0.056(4) -0.006(3) 0.011(3) 0.010(3) F4B 0.043(3) 0.085(3) 0.057(3) -0.003(3) 0.014(3) 0.011(3) F5B 0.049(3) 0.094(4) 0.058(3) -0.001(3) 0.017(3) 0.006(3) C19B 0.0432(18) 0.086(2) 0.0578(18) -0.0021(18) 0.0151(17) 0.0032(18) C20B 0.0423(18) 0.085(2) 0.0566(19) -0.0030(18) 0.0148(18) 0.0060(18) _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 O1 H1 0.85(7) . ? O1 C6 1.351(5) . ? O2 C9 1.323(5) . ? O2 C10 1.479(6) . ? O3 C9 1.215(5) . ? O4 C11 1.227(5) . ? O5 C11 1.349(4) . ? O5 C12 1.457(5) . ? N1 H1A 0.85(5) . ? N1 C1 1.448(5) . ? N1 C11 1.329(6) . ? C1 H1B 1.0000 . ? C1 C2 1.530(6) . ? C1 C9 1.515(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.509(6) . ? C3 C4 1.382(5) . ? C3 C8 1.394(5) . ? C4 H4 0.9500 . ? C4 C5 1.389(6) . ? C5 C6 1.413(5) . ? C5 C19A 1.506(7) . ? C5 C19B 1.461(18) . ? C6 C7 1.395(5) . ? C7 H7 0.9500 . ? C7 C8 1.373(6) . ? C8 H8 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.501(5) . ? C13 C14 1.400(7) . ? C13 C18 1.370(7) . ? C14 H14 0.9500 . ? C14 C15 1.380(7) . ? C15 H15 0.9500 . ? C15 C16 1.362(12) . ? C16 H16 0.9500 . ? C16 C17 1.405(13) . ? C17 H17 0.9500 . ? C17 C18 1.394(9) . ? C18 H18 0.9500 . ? F1A C19A 1.345(8) . ? F2A C19A 1.364(7) . ? F3A C20A 1.316(7) . ? F4A C20A 1.334(9) . ? F5A C20A 1.345(8) . ? C19A C20A 1.509(11) . ? F1B C19B 1.45(2) . ? F2B C19B 1.44(2) . ? F3B C20B 1.39(2) . ? F4B C20B 1.41(2) . ? F5B C20B 1.39(2) . ? C19B C20B 1.434(17) . ? 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 C6 O1 H1 111(4) . . ? C9 O2 C10 115.9(4) . . ? C11 O5 C12 115.7(3) . . ? C1 N1 H1A 112(3) . . ? C11 N1 H1A 123(3) . . ? C11 N1 C1 124.9(3) . . ? N1 C1 H1B 109.6 . . ? N1 C1 C2 110.7(3) . . ? N1 C1 C9 110.2(3) . . ? C2 C1 H1B 109.6 . . ? C9 C1 H1B 109.6 . . ? C9 C1 C2 107.1(3) . . ? C1 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C3 C2 C1 114.5(3) . . ? C3 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? C4 C3 C2 121.2(3) . . ? C4 C3 C8 117.6(4) . . ? C8 C3 C2 121.2(3) . . ? C3 C4 H4 119.0 . . ? C3 C4 C5 122.0(4) . . ? C5 C4 H4 119.0 . . ? C4 C5 C6 119.6(4) . . ? C4 C5 C19A 119.4(4) . . ? C4 C5 C19B 117.8(12) . . ? C6 C5 C19A 121.0(4) . . ? C6 C5 C19B 119.2(12) . . ? O1 C6 C5 119.5(3) . . ? O1 C6 C7 122.2(3) . . ? C7 C6 C5 118.2(4) . . ? C6 C7 H7 119.7 . . ? C8 C7 C6 120.7(3) . . ? C8 C7 H7 119.7 . . ? C3 C8 H8 119.1 . . ? C7 C8 C3 121.8(3) . . ? C7 C8 H8 119.1 . . ? O2 C9 C1 112.5(3) . . ? O3 C9 O2 123.8(4) . . ? O3 C9 C1 123.6(3) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 O5 122.3(4) . . ? O4 C11 N1 126.6(3) . . ? N1 C11 O5 111.1(3) . . ? O5 C12 H12A 110.3 . . ? O5 C12 H12B 110.3 . . ? O5 C12 C13 106.9(3) . . ? H12A C12 H12B 108.6 . . ? C13 C12 H12A 110.3 . . ? C13 C12 H12B 110.3 . . ? C14 C13 C12 118.8(4) . . ? C18 C13 C12 120.6(5) . . ? C18 C13 C14 120.5(4) . . ? C13 C14 H14 120.3 . . ? C15 C14 C13 119.4(5) . . ? C15 C14 H14 120.3 . . ? C14 C15 H15 119.6 . . ? C16 C15 C14 120.8(7) . . ? C16 C15 H15 119.6 . . ? C15 C16 H16 120.0 . . ? C15 C16 C17 119.9(5) . . ? C17 C16 H16 120.0 . . ? C16 C17 H17 120.2 . . ? C18 C17 C16 119.6(6) . . ? C18 C17 H17 120.2 . . ? C13 C18 C17 119.7(6) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C5 C19A C20A 115.1(5) . . ? F1A C19A C5 112.9(5) . . ? F1A C19A F2A 106.6(5) . . ? F1A C19A C20A 107.0(6) . . ? F2A C19A C5 110.1(5) . . ? F2A C19A C20A 104.6(5) . . ? F3A C20A F4A 108.0(5) . . ? F3A C20A F5A 106.9(6) . . ? F3A C20A C19A 112.7(6) . . ? F4A C20A F5A 107.1(7) . . ? F4A C20A C19A 110.8(6) . . ? F5A C20A C19A 111.1(5) . . ? F1B C19B C5 129(2) . . ? F2B C19B C5 119(2) . . ? F2B C19B F1B 91.0(19) . . ? C20B C19B C5 114.2(19) . . ? C20B C19B F1B 98(2) . . ? C20B C19B F2B 100(2) . . ? F3B C20B F4B 105(2) . . ? F3B C20B F5B 109(2) . . ? F3B C20B C19B 111(2) . . ? F5B C20B F4B 108(2) . . ? F5B C20B C19B 121(2) . . ? C19B C20B F4B 102(2) . . ? 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 C6 C7 C8 179.1(4) . . . . ? O5 C12 C13 C14 -83.4(5) . . . . ? O5 C12 C13 C18 98.4(5) . . . . ? N1 C1 C2 C3 -60.8(4) . . . . ? N1 C1 C9 O2 143.3(4) . . . . ? N1 C1 C9 O3 -39.5(5) . . . . ? C1 N1 C11 O4 -5.9(6) . . . . ? C1 N1 C11 O5 175.1(3) . . . . ? C1 C2 C3 C4 83.6(5) . . . . ? C1 C2 C3 C8 -97.3(4) . . . . ? C2 C1 C9 O2 -96.2(4) . . . . ? C2 C1 C9 O3 81.0(5) . . . . ? C2 C3 C4 C5 177.4(4) . . . . ? C2 C3 C8 C7 -178.0(4) . . . . ? C3 C4 C5 C6 1.6(7) . . . . ? C3 C4 C5 C19A -177.2(5) . . . . ? C3 C4 C5 C19B 160.6(14) . . . . ? C4 C3 C8 C7 1.1(6) . . . . ? C4 C5 C6 O1 -179.7(4) . . . . ? C4 C5 C6 C7 -0.8(6) . . . . ? C4 C5 C19A F1A 136.1(5) . . . . ? C4 C5 C19A F2A 17.1(8) . . . . ? C4 C5 C19A C20A -100.7(6) . . . . ? C4 C5 C19B F1B -124(2) . . . . ? C4 C5 C19B F2B -6(3) . . . . ? C4 C5 C19B C20B 113.1(19) . . . . ? C5 C6 C7 C8 0.2(6) . . . . ? C5 C19A C20A F3A 179.2(5) . . . . ? C5 C19A C20A F4A 58.1(8) . . . . ? C5 C19A C20A F5A -60.9(7) . . . . ? C5 C19B C20B F3B 56(3) . . . . ? C5 C19B C20B F4B -55(3) . . . . ? C5 C19B C20B F5B -176(2) . . . . ? C6 C5 C19A F1A -42.8(7) . . . . ? C6 C5 C19A F2A -161.8(5) . . . . ? C6 C5 C19A C20A 80.4(7) . . . . ? C6 C5 C19B F1B 35(3) . . . . ? C6 C5 C19B F2B 153.5(19) . . . . ? C6 C5 C19B C20B -88(2) . . . . ? C6 C7 C8 C3 -0.3(6) . . . . ? C8 C3 C4 C5 -1.8(6) . . . . ? C9 C1 C2 C3 179.0(3) . . . . ? C10 O2 C9 O3 3.9(6) . . . . ? C10 O2 C9 C1 -178.9(4) . . . . ? C11 O5 C12 C13 -176.9(4) . . . . ? C11 N1 C1 C2 134.5(4) . . . . ? C11 N1 C1 C9 -107.2(4) . . . . ? C12 O5 C11 O4 -0.3(6) . . . . ? C12 O5 C11 N1 178.7(4) . . . . ? C12 C13 C14 C15 -179.2(5) . . . . ? C12 C13 C18 C17 178.8(5) . . . . ? C13 C14 C15 C16 0.8(9) . . . . ? C14 C13 C18 C17 0.6(8) . . . . ? C14 C15 C16 C17 -0.3(10) . . . . ? C15 C16 C17 C18 -0.1(10) . . . . ? C16 C17 C18 C13 -0.1(9) . . . . ? C18 C13 C14 C15 -1.0(8) . . . . ? F1A C19A C20A F3A -54.5(7) . . . . ? F1A C19A C20A F4A -175.6(5) . . . . ? F1A C19A C20A F5A 65.4(6) . . . . ? F2A C19A C20A F3A 58.3(7) . . . . ? F2A C19A C20A F4A -62.8(6) . . . . ? F2A C19A C20A F5A 178.2(5) . . . . ? C19A C5 C6 O1 -0.9(7) . . . . ? C19A C5 C6 C7 178.0(5) . . . . ? F1B C19B C20B F3B -83(2) . . . . ? F1B C19B C20B F4B 166(2) . . . . ? F1B C19B C20B F5B 46(3) . . . . ? F2B C19B C20B F3B -175(2) . . . . ? F2B C19B C20B F4B 74(2) . . . . ? F2B C19B C20B F5B -46(3) . . . . ? C19B C5 C6 O1 21.6(14) . . . . ? C19B C5 C6 C7 -159.5(13) . . . . ? _shelx_res_file ; jk1392a.res created by SHELXL-2014/7 TITL jk1392a_a.res in I2 REM Old TITL jk1392A in I2/m REM SHELXT solution in I2 REM R1 0.157, Rweak 0.038, Alpha 0.001, Orientation as input REM Flack x = -0.009 ( 0.068 ) from Parsons' quotients REM Formula found by SHELXT: C22 F9 CELL 1.54184 20.3374 7.1756 14.0098 90 92.999 90 ZERR 4 0.0007 0.0003 0.0007 0 0.004 0 LATT -2 SYMM -X,+Y,-Z SFAC C H F N O UNIT 80 72 20 4 20 DFIX 1.5 C20B C19B SADI 0.04 F2B C20B F2B F1B C20B F1B SADI C19B C5 C19B F2B C19B C20B C19B F1B SADI 0.04 F5B F4B F5B F3B F4B F3B SADI C20B F5B C20B F4B C20B C19B C20B F3B SIMU 0.002 0.004 2 F1A > C20B L.S. 10 PLAN 5 SIZE 0.12 0.085 0.015 TEMP -173.15 BOND $H list 4 MORE -1 CONF fmap 2 53 acta REM REM REM WGHT 0.077200 2.356800 FVAR 0.38398 0.87226 O1 5 0.233978 0.297357 0.074418 11.00000 0.02996 0.05793 = 0.04104 -0.00303 0.00322 0.00082 H1 2 0.192086 0.299257 0.073089 11.00000 0.06197 O2 5 0.359968 0.400143 0.662427 11.00000 0.03750 0.05400 = 0.04326 0.00122 0.01334 0.00459 O3 5 0.455178 0.285317 0.614405 11.00000 0.02860 0.04049 = 0.04406 0.00290 0.00600 -0.00076 O4 5 0.398349 0.783334 0.428694 11.00000 0.02861 0.03513 = 0.04785 0.00524 0.00553 0.00181 O5 5 0.492859 0.678072 0.370390 11.00000 0.02585 0.03780 = 0.04766 0.00573 0.01070 -0.00230 N1 4 0.428807 0.477484 0.440803 11.00000 0.02420 0.03385 = 0.04472 0.00013 0.00710 0.00159 H1A 2 0.457260 0.394071 0.430590 11.00000 0.03058 C1 1 0.376080 0.408320 0.496633 11.00000 0.02486 0.03365 = 0.04278 0.00155 0.00772 0.00022 AFIX 13 H1B 2 0.341009 0.505467 0.499824 11.00000 -1.20000 AFIX 0 C2 1 0.346571 0.230021 0.452482 11.00000 0.02934 0.03712 = 0.04437 0.00342 0.00393 -0.00199 AFIX 23 H2A 2 0.381502 0.134012 0.451787 11.00000 -1.20000 H2B 2 0.312110 0.183619 0.493831 11.00000 -1.20000 AFIX 0 C3 1 0.316804 0.252842 0.352198 11.00000 0.02783 0.02944 = 0.04499 0.00132 0.00253 -0.00133 C4 1 0.355351 0.245011 0.273927 11.00000 0.02653 0.04176 = 0.04777 -0.00085 0.00520 0.00295 AFIX 43 H4 2 0.401607 0.230122 0.284034 11.00000 -1.20000 AFIX 0 C5 1 0.328534 0.258242 0.180948 11.00000 0.02888 0.04544 = 0.04349 -0.00270 0.00871 0.00060 C6 1 0.260028 0.285294 0.164911 11.00000 0.02769 0.03482 = 0.04486 -0.00149 0.00382 0.00041 C7 1 0.221342 0.295437 0.244120 11.00000 0.02345 0.03375 = 0.05206 -0.00205 0.00429 -0.00170 AFIX 43 H7 2 0.175151 0.313208 0.235002 11.00000 -1.20000 AFIX 0 C8 1 0.249347 0.279997 0.335117 11.00000 0.02719 0.03567 = 0.04613 0.00010 0.00965 -0.00380 AFIX 43 H8 2 0.221988 0.288046 0.387885 11.00000 -1.20000 AFIX 0 C9 1 0.402277 0.359903 0.596826 11.00000 0.02826 0.03576 = 0.04451 0.00020 0.01119 -0.00487 C10 1 0.382304 0.360247 0.762481 11.00000 0.05878 0.06820 = 0.04874 -0.00437 0.01259 -0.00041 AFIX 137 H10A 2 0.381949 0.225325 0.773288 11.00000 -1.50000 H10B 2 0.352664 0.420918 0.805852 11.00000 -1.50000 H10C 2 0.427100 0.408059 0.774614 11.00000 -1.50000 AFIX 0 C11 1 0.436472 0.654411 0.415560 11.00000 0.02418 0.04026 = 0.03360 -0.00121 0.00260 -0.00339 C12 1 0.505478 0.866825 0.337582 11.00000 0.03819 0.03954 = 0.06641 0.01335 0.01823 0.00075 AFIX 23 H12A 2 0.510487 0.953052 0.392646 11.00000 -1.20000 H12B 2 0.468520 0.910834 0.294588 11.00000 -1.20000 AFIX 0 C13 1 0.567924 0.859686 0.285105 11.00000 0.04082 0.03498 = 0.05182 0.00440 0.01734 -0.00347 C14 1 0.628306 0.869074 0.337618 11.00000 0.04220 0.04538 = 0.06198 0.00121 0.00932 0.00090 AFIX 43 H14 2 0.629512 0.878184 0.405336 11.00000 -1.20000 AFIX 0 C15 1 0.686087 0.864982 0.290159 11.00000 0.04389 0.05343 = 0.12847 -0.00164 0.02807 -0.00442 AFIX 43 H15 2 0.727137 0.869707 0.325695 11.00000 -1.20000 AFIX 0 C16 1 0.684983 0.854254 0.193003 11.00000 0.07952 0.06820 = 0.12552 -0.00975 0.07239 -0.01428 AFIX 43 H16 2 0.725086 0.852100 0.161160 11.00000 -1.20000 AFIX 0 C17 1 0.624502 0.846380 0.139949 11.00000 0.12998 0.06143 = 0.07078 -0.01282 0.06380 -0.02080 AFIX 43 H17 2 0.623518 0.839095 0.072182 11.00000 -1.20000 AFIX 0 C18 1 0.565919 0.849321 0.187364 11.00000 0.07299 0.05140 = 0.05277 -0.00095 0.01295 -0.01584 AFIX 43 H18 2 0.524794 0.844160 0.152041 11.00000 -1.20000 AFIX 0 PART 1 F1A 3 0.347152 0.130968 0.028016 21.00000 0.04773 0.07781 = 0.05293 -0.01343 0.00946 0.01153 F2A 3 0.431228 0.160560 0.129003 21.00000 0.03946 0.09141 = 0.05822 -0.00025 0.01294 0.01898 F3A 3 0.431424 0.397939 -0.017133 21.00000 0.05167 0.11242 = 0.06356 0.01117 0.03108 0.00425 F4A 3 0.422347 0.533174 0.117960 21.00000 0.06394 0.09807 = 0.07542 0.00089 0.01859 -0.02948 F5A 3 0.338699 0.513309 0.017450 21.00000 0.05160 0.07215 = 0.07024 0.01780 0.02546 0.00460 C19A 1 0.372869 0.239881 0.098674 21.00000 0.03794 0.08113 = 0.05375 -0.00411 0.01389 0.00717 C20A 1 0.392041 0.421459 0.053524 21.00000 0.04363 0.08548 = 0.05861 -0.00010 0.01734 0.00091 PART 0 PART 2 F1B 3 0.366596 0.461940 0.038515 -21.00000 0.04786 0.08903 = 0.06300 0.00531 0.02092 -0.00272 F2B 3 0.439820 0.358807 0.131425 -21.00000 0.04513 0.08969 = 0.06090 -0.00111 0.01590 -0.00050 F3B 3 0.322745 0.102120 -0.002883 -21.00000 0.04221 0.08068 = 0.05621 -0.00607 0.01069 0.00965 F4B 3 0.404984 0.014670 0.097584 -21.00000 0.04315 0.08515 = 0.05663 -0.00319 0.01351 0.01100 F5B 3 0.426636 0.184873 -0.033722 -21.00000 0.04921 0.09432 = 0.05806 -0.00128 0.01748 0.00630 C19B 1 0.372512 0.308684 0.105889 -21.00000 0.04317 0.08567 = 0.05781 -0.00206 0.01509 0.00316 C20B 1 0.382599 0.162992 0.038147 -21.00000 0.04225 0.08465 = 0.05655 -0.00298 0.01480 0.00603 HKLF 4 REM jk1392a_a.res in I2 REM R1 = 0.0567 for 3939 Fo > 4sig(Fo) and 0.0606 for all 4292 data REM 353 parameters refined using 251 restraints END WGHT 0.0770 2.3660 REM Highest difference peak 0.418, deepest hole -0.413, 1-sigma level 0.057 Q1 1 0.3647 0.2828 0.8237 11.00000 0.05 0.42 Q2 1 0.3206 0.3651 0.1942 11.00000 0.05 0.25 Q3 1 0.6402 0.7449 0.1592 11.00000 0.05 0.24 Q4 1 0.3928 0.6034 0.1193 11.00000 0.05 0.22 Q5 1 0.2409 0.1684 0.0780 11.00000 0.05 0.21 ; _shelx_res_checksum 51563 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.198 _oxdiff_exptl_absorpt_empirical_full_min 0.860