#------------------------------------------------------------------------------ #$Date: 2019-11-08 03:58:01 +0200 (Fri, 08 Nov 2019) $ #$Revision: 225244 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156790.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7156790 loop_ _publ_author_name 'Kong, Hongjun' 'Li, Qingrui' 'Yin, Yunnian' 'Huang, Mengmeng' 'Kim, Jung Keun' 'Zhu, Yu' 'Li, Yabo' 'Wu, Yangjie' _publ_section_title ; An efficient light on-off one-pot method for the synthesis of 3-styryl coumarins from aryl alkynoates. ; _journal_issue 18 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4621 _journal_page_last 4628 _journal_paper_doi 10.1039/c9ob00421a _journal_volume 17 _journal_year 2019 _chemical_formula_moiety 'C24 H17 F O2' _chemical_formula_sum 'C24 H17 F O2' _chemical_formula_weight 356.37 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2018-08-25 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-01-04 deposited with the CCDC. 2019-04-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.548(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.4181(5) _cell_length_b 9.8070(5) _cell_length_c 18.1210(7) _cell_measurement_reflns_used 1814 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.0780 _cell_measurement_theta_min 4.9600 _cell_volume 1813.95(15) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -102.00 -14.50 0.5000 3.6000 omega____ theta____ kappa____ phi______ frames - -33.5000 -57.0000 150.0000 175 #__ type_ start__ end____ width___ exp.time_ 2 omega -40.00 -15.00 0.5000 3.6000 omega____ theta____ kappa____ phi______ frames - -33.5000 -57.0000 150.0000 50 #__ type_ start__ end____ width___ exp.time_ 3 omega -29.00 29.00 0.5000 3.6000 omega____ theta____ kappa____ phi______ frames - 36.4734 -19.0000 30.0000 116 #__ type_ start__ end____ width___ exp.time_ 4 omega -102.00 -61.00 0.5000 3.6000 omega____ theta____ kappa____ phi______ frames - -33.5000 -57.0000 150.0000 82 #__ type_ start__ end____ width___ exp.time_ 5 omega 57.00 97.00 0.5000 3.6000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 90.0000 80 #__ type_ start__ end____ width___ exp.time_ 6 omega 80.00 105.00 0.5000 3.6000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 -60.0000 50 #__ type_ start__ end____ width___ exp.time_ 7 omega 42.00 102.00 0.5000 3.6000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 60.0000 120 #__ type_ start__ end____ width___ exp.time_ 8 omega 47.00 74.00 0.5000 3.6000 omega____ theta____ kappa____ phi______ frames - 36.4734 -19.0000 30.0000 54 #__ type_ start__ end____ width___ exp.time_ 9 omega -29.00 3.00 0.5000 3.6000 omega____ theta____ kappa____ phi______ frames - 36.4734 -77.0000 150.0000 64 #__ type_ start__ end____ width___ exp.time_ 10 omega 45.00 87.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 120.0000 84 #__ type_ start__ end____ width___ exp.time_ 11 omega 139.00 167.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 90.0000 56 #__ type_ start__ end____ width___ exp.time_ 12 omega 37.00 69.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -120.0000 64 #__ type_ start__ end____ width___ exp.time_ 13 omega 51.00 77.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 14 omega 38.00 92.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 -30.0000 108 #__ type_ start__ end____ width___ exp.time_ 15 omega 39.00 77.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 0.0000 76 #__ type_ start__ end____ width___ exp.time_ 16 omega 38.00 85.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -90.0000 94 #__ type_ start__ end____ width___ exp.time_ 17 omega 70.00 98.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 60.0000 56 #__ type_ start__ end____ width___ exp.time_ 18 omega 50.00 89.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 30.0000 78 #__ type_ start__ end____ width___ exp.time_ 19 omega 41.00 99.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 -180.0000 116 #__ type_ start__ end____ width___ exp.time_ 20 omega 40.00 156.00 0.5000 27.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 0.0000 90.0000 232 #__ type_ start__ end____ width___ exp.time_ 21 omega -34.00 10.00 0.5000 3.6000 omega____ theta____ kappa____ phi______ frames - -33.5000 37.0000 -90.0000 88 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1252546000 _diffrn_orient_matrix_UB_12 -0.0861670000 _diffrn_orient_matrix_UB_13 0.0223394000 _diffrn_orient_matrix_UB_21 -0.0293830000 _diffrn_orient_matrix_UB_22 -0.0696735000 _diffrn_orient_matrix_UB_23 -0.0777908000 _diffrn_orient_matrix_UB_31 0.0788998000 _diffrn_orient_matrix_UB_32 0.1113952000 _diffrn_orient_matrix_UB_33 -0.0312374000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_unetI/netI 0.0334 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 6891 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 67.065 _diffrn_reflns_theta_max 67.065 _diffrn_reflns_theta_min 4.332 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.722 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92887 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.305 _exptl_crystal_description prism _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.240 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 245 _refine_ls_number_reflns 3224 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0586 _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^)+(0.0935P)^2^+0.2786P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1615 _refine_ls_wR_factor_ref 0.1846 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2216 _reflns_number_total 3224 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201808347.res created by SHELXL-2014/7 TITL 201808347 in P21/c #14 REM reset to P21/c #14 CELL 1.54184 10.418097 9.806959 18.121034 90 101.5481 90 ZERR 4 0.000521 0.000461 0.000695 0 0.0042 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F O UNIT 96 68 4 8 L.S. 9 0 0 PLAN 20 SIZE 0.09 0.1 0.11 MPLA C1 C2 C11 C18 C19 O1 MPLA C5 C6 C7 C8 C9 C10 MPLA C12 C13 C14 C15 C16 C17 MPLA C18 C19 C20 C21 C22 C23 BOND $h conf fmap 2 acta REM REM REM WGHT 0.093500 0.278600 FVAR 5.38360 C1 1 1.056767 0.277418 0.484424 11.00000 0.07602 0.06492 = 0.04834 0.00511 0.00597 0.00773 C2 1 0.983189 0.323476 0.410834 11.00000 0.06027 0.05700 = 0.04590 0.00527 0.00925 0.00696 C3 1 0.873730 0.240992 0.371761 11.00000 0.06585 0.06151 = 0.05478 0.00554 0.00792 0.00819 AFIX 43 H3 2 0.830944 0.274509 0.325315 11.00000 -1.20000 AFIX 0 C4 1 0.826152 0.123676 0.393396 11.00000 0.07090 0.06120 = 0.05717 0.00692 0.00861 0.00323 AFIX 43 H4 2 0.861868 0.090337 0.441137 11.00000 -1.20000 AFIX 0 C5 1 0.720735 0.044675 0.345977 11.00000 0.06564 0.05679 = 0.07052 0.00349 0.01256 0.00518 C6 1 0.674443 0.071868 0.270252 11.00000 0.10030 0.06643 = 0.07484 0.00904 -0.00208 -0.00811 AFIX 43 H6 2 0.709990 0.144679 0.248262 11.00000 -1.20000 AFIX 0 C7 1 0.579399 -0.003764 0.227222 11.00000 0.11369 0.08120 = 0.09716 -0.00084 -0.02041 -0.00805 AFIX 43 H7 2 0.553287 0.015258 0.176138 11.00000 -1.20000 AFIX 0 C8 1 0.520699 -0.109689 0.259058 11.00000 0.08349 0.09183 = 0.12869 -0.01555 -0.00224 -0.01092 AFIX 43 H8 2 0.451856 -0.158688 0.230470 11.00000 -1.20000 AFIX 0 C9 1 0.566359 -0.140725 0.333697 11.00000 0.09988 0.08456 = 0.11248 0.00020 0.02337 -0.02693 AFIX 43 H9 2 0.530638 -0.213601 0.355538 11.00000 -1.20000 AFIX 0 C10 1 0.664962 -0.063962 0.376140 11.00000 0.09179 0.08191 = 0.08619 0.00597 0.01587 -0.01314 AFIX 43 H10 2 0.694730 -0.086077 0.426571 11.00000 -1.20000 AFIX 0 C11 1 1.019235 0.439725 0.378931 11.00000 0.05778 0.05705 = 0.04838 0.00142 0.00491 0.00888 C12 1 0.947385 0.487828 0.303079 11.00000 0.06300 0.05627 = 0.04711 0.00614 0.00251 -0.00109 C13 1 0.981124 0.439930 0.238413 11.00000 0.07023 0.06302 = 0.05477 0.00216 0.00651 0.00510 AFIX 43 H13 2 1.049012 0.377168 0.241993 11.00000 -1.20000 AFIX 0 C14 1 0.916236 0.482999 0.167696 11.00000 0.07619 0.07762 = 0.04668 -0.00299 0.00747 -0.01024 AFIX 43 H14 2 0.940581 0.451574 0.124059 11.00000 -1.20000 AFIX 0 C15 1 0.815720 0.572878 0.164624 11.00000 0.06620 0.07749 = 0.05146 0.01615 -0.00573 -0.00418 C16 1 0.779261 0.623616 0.226904 11.00000 0.07234 0.09091 = 0.06660 0.01655 0.00160 0.02213 AFIX 43 H16 2 0.710940 0.685992 0.222699 11.00000 -1.20000 AFIX 0 C17 1 0.846106 0.580466 0.297126 11.00000 0.07064 0.07914 = 0.05687 0.00620 0.00901 0.01719 AFIX 43 H17 2 0.822446 0.614249 0.340468 11.00000 -1.20000 AFIX 0 C18 1 1.130629 0.517743 0.416298 11.00000 0.05987 0.06215 = 0.05105 -0.00155 0.00498 0.00639 C19 1 1.202418 0.470297 0.484049 11.00000 0.06238 0.06059 = 0.04775 -0.00294 0.00301 0.00761 C20 1 1.312854 0.538386 0.522965 11.00000 0.06904 0.07590 = 0.05630 -0.00949 -0.00120 0.00662 AFIX 43 H20 2 1.359537 0.502626 0.567935 11.00000 -1.20000 AFIX 0 C21 1 1.353220 0.657975 0.495344 11.00000 0.06495 0.07952 = 0.06803 -0.01600 0.00578 0.00039 C22 1 1.280990 0.708651 0.427844 11.00000 0.06911 0.06801 = 0.07653 -0.00126 0.00608 -0.00515 AFIX 43 H22 2 1.306250 0.790136 0.408690 11.00000 -1.20000 AFIX 0 C23 1 1.173002 0.640393 0.389003 11.00000 0.06616 0.07056 = 0.06415 0.00868 -0.00021 -0.00212 AFIX 43 H23 2 1.127165 0.676119 0.343809 11.00000 -1.20000 AFIX 0 C24 1 1.471025 0.734787 0.536873 11.00000 0.07254 0.10522 = 0.08865 -0.02689 -0.00156 -0.01120 AFIX 137 H24A 2 1.541918 0.672219 0.553118 11.00000 -1.50000 H24B 2 1.449380 0.779371 0.579943 11.00000 -1.50000 H24C 2 1.496835 0.801712 0.504019 11.00000 -1.50000 AFIX 0 F1 3 0.751587 0.614898 0.095559 11.00000 0.10704 0.14369 = 0.05691 0.02863 -0.01316 0.01361 O1 4 1.166721 0.353240 0.516264 11.00000 0.08042 0.07181 = 0.05007 0.00797 -0.00456 0.00263 O2 4 1.033839 0.183024 0.520677 11.00000 0.10164 0.08601 = 0.06553 0.02807 0.00502 -0.00263 HKLF 4 REM 201808347 in P21/c #14 REM R1 = 0.0586 for 2216 Fo > 4sig(Fo) and 0.0838 for all 3224 data REM 245 parameters refined using 0 restraints END WGHT 0.0935 0.2786 REM Highest difference peak 0.240, deepest hole -0.145, 1-sigma level 0.040 Q1 1 0.9128 0.1327 0.4751 11.00000 0.05 0.24 Q2 1 1.0741 0.2618 0.5455 11.00000 0.05 0.22 Q3 1 0.8691 0.4267 0.2889 11.00000 0.05 0.21 Q4 1 0.7028 0.1915 0.2762 11.00000 0.05 0.19 Q5 1 0.9050 0.3392 0.3488 11.00000 0.05 0.18 Q6 1 1.5023 0.6635 0.5875 11.00000 0.05 0.18 Q7 1 1.4685 0.8439 0.5243 11.00000 0.05 0.18 Q8 1 0.7885 0.5095 0.2847 11.00000 0.05 0.16 Q9 1 1.3010 0.5813 0.4789 11.00000 0.05 0.16 Q10 1 0.9830 0.3856 0.4084 11.00000 0.05 0.15 Q11 1 0.7502 0.0118 0.4068 11.00000 0.05 0.15 Q12 1 0.7945 0.1922 0.3516 11.00000 0.05 0.15 Q13 1 0.9992 0.3242 0.4410 11.00000 0.05 0.15 Q14 1 1.5658 0.7154 0.5034 11.00000 0.05 0.15 Q15 1 1.3470 0.7925 0.4458 11.00000 0.05 0.14 Q16 1 0.7666 0.5554 0.2551 11.00000 0.05 0.14 Q17 1 0.7396 0.5510 0.2100 11.00000 0.05 0.13 Q18 1 0.5010 -0.0617 0.3145 11.00000 0.05 0.13 Q19 1 1.1514 0.5037 0.4602 11.00000 0.05 0.13 Q20 1 1.0787 0.1692 0.4849 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0586 for 2216 Fo > 4sig(Fo) and 0.0838 for all 7248 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.24, deepest hole -0.14 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0838 REM R1_gt = 0.0586 REM wR_ref = 0.1846 REM GOOF = 1.023 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 7248 REM Reflections_gt = 2216 REM Parameters = n/a REM Hole = -0.14 REM Peak = 0.24 REM Flack = n/a ; _cod_data_source_file c9ob00421a2.cif _cod_data_source_block 201808347 _cod_depositor_comments 'Adding full bibliography for 7156785--7156790.cif.' _cod_original_cell_volume 1813.94(15) _cod_database_code 7156790 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C15H15O3N2 _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. ; _shelx_estimated_absorpt_t_max 0.938 _shelx_estimated_absorpt_t_min 0.925 _reflns_odcompleteness_completeness 99.51 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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: C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16), C17(H17), C20(H20), C22(H22), C23(H23) 2.b Idealised Me refined as rotating group: C24(H24A,H24B,H24C) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn C1 C 1.0568(3) 0.2774(3) 0.48442(13) 0.0640(7) Uani 1 1 d . C2 C 0.9832(2) 0.3235(3) 0.41083(12) 0.0546(6) Uani 1 1 d . C3 C 0.8737(3) 0.2410(3) 0.37176(14) 0.0613(6) Uani 1 1 d . H3 H 0.8309 0.2745 0.3253 0.074 Uiso 1 1 calc R C4 C 0.8262(3) 0.1237(3) 0.39340(14) 0.0637(7) Uani 1 1 d . H4 H 0.8619 0.0903 0.4411 0.076 Uiso 1 1 calc R C5 C 0.7207(3) 0.0447(3) 0.34598(15) 0.0645(6) Uani 1 1 d . C6 C 0.6744(4) 0.0719(3) 0.27025(17) 0.0833(9) Uani 1 1 d . H6 H 0.7100 0.1447 0.2483 0.100 Uiso 1 1 calc R C7 C 0.5794(4) -0.0038(4) 0.2272(2) 0.1031(13) Uani 1 1 d . H7 H 0.5533 0.0153 0.1761 0.124 Uiso 1 1 calc R C8 C 0.5207(4) -0.1097(4) 0.2591(3) 0.1046(12) Uani 1 1 d . H8 H 0.4519 -0.1587 0.2305 0.126 Uiso 1 1 calc R C9 C 0.5664(4) -0.1407(4) 0.3337(2) 0.0987(11) Uani 1 1 d . H9 H 0.5306 -0.2136 0.3555 0.118 Uiso 1 1 calc R C10 C 0.6650(4) -0.0640(4) 0.37614(19) 0.0869(9) Uani 1 1 d . H10 H 0.6947 -0.0861 0.4266 0.104 Uiso 1 1 calc R C11 C 1.0192(2) 0.4397(3) 0.37893(12) 0.0552(6) Uani 1 1 d . C12 C 0.9474(3) 0.4878(3) 0.30308(12) 0.0566(6) Uani 1 1 d . C13 C 0.9811(3) 0.4399(3) 0.23841(13) 0.0635(7) Uani 1 1 d . H13 H 1.0490 0.3772 0.2420 0.076 Uiso 1 1 calc R C14 C 0.9162(3) 0.4830(3) 0.16770(13) 0.0675(7) Uani 1 1 d . H14 H 0.9406 0.4516 0.1241 0.081 Uiso 1 1 calc R C15 C 0.8157(3) 0.5729(3) 0.16462(14) 0.0675(7) Uani 1 1 d . C16 C 0.7793(3) 0.6236(4) 0.22690(16) 0.0783(8) Uani 1 1 d . H16 H 0.7109 0.6860 0.2227 0.094 Uiso 1 1 calc R C17 C 0.8461(3) 0.5805(3) 0.29713(14) 0.0694(7) Uani 1 1 d . H17 H 0.8224 0.6142 0.3405 0.083 Uiso 1 1 calc R C18 C 1.1306(2) 0.5177(3) 0.41630(13) 0.0585(6) Uani 1 1 d . C19 C 1.2024(3) 0.4703(3) 0.48405(12) 0.0580(6) Uani 1 1 d . C20 C 1.3129(3) 0.5384(3) 0.52297(15) 0.0690(7) Uani 1 1 d . H20 H 1.3595 0.5026 0.5679 0.083 Uiso 1 1 calc R C21 C 1.3532(3) 0.6580(3) 0.49534(16) 0.0719(8) Uani 1 1 d . C22 C 1.2810(3) 0.7087(3) 0.42784(16) 0.0724(7) Uani 1 1 d . H22 H 1.3063 0.7901 0.4087 0.087 Uiso 1 1 calc R C23 C 1.1730(3) 0.6404(3) 0.38900(15) 0.0688(7) Uani 1 1 d . H23 H 1.1272 0.6761 0.3438 0.083 Uiso 1 1 calc R C24 C 1.4710(3) 0.7348(4) 0.53687(19) 0.0913(10) Uani 1 1 d . H24A H 1.5419 0.6722 0.5531 0.137 Uiso 1 1 calc GR H24B H 1.4494 0.7794 0.5799 0.137 Uiso 1 1 calc GR H24C H 1.4968 0.8017 0.5040 0.137 Uiso 1 1 calc GR F1 F 0.7516(2) 0.6149(3) 0.09556(9) 0.1067(7) Uani 1 1 d . O1 O 1.1667(2) 0.3532(2) 0.51626(9) 0.0699(5) Uani 1 1 d . O2 O 1.0338(2) 0.1830(2) 0.52068(11) 0.0860(7) Uani 1 1 d . 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 C1 0.0760(16) 0.0649(16) 0.0483(12) 0.0051(12) 0.0060(11) 0.0077(14) C2 0.0603(13) 0.0570(14) 0.0459(11) 0.0053(10) 0.0092(9) 0.0070(11) C3 0.0658(15) 0.0615(15) 0.0548(12) 0.0055(11) 0.0079(11) 0.0082(12) C4 0.0709(16) 0.0612(16) 0.0572(13) 0.0069(11) 0.0086(11) 0.0032(13) C5 0.0656(15) 0.0568(15) 0.0705(15) 0.0035(12) 0.0126(12) 0.0052(12) C6 0.100(2) 0.0664(18) 0.0748(18) 0.0090(14) -0.0021(16) -0.0081(17) C7 0.114(3) 0.081(2) 0.097(2) -0.0008(19) -0.020(2) -0.008(2) C8 0.083(2) 0.092(3) 0.129(3) -0.016(2) -0.002(2) -0.011(2) C9 0.100(3) 0.085(2) 0.112(3) 0.000(2) 0.023(2) -0.027(2) C10 0.092(2) 0.082(2) 0.086(2) 0.0060(16) 0.0159(17) -0.0131(19) C11 0.0578(13) 0.0571(14) 0.0484(11) 0.0014(10) 0.0049(9) 0.0089(11) C12 0.0630(14) 0.0563(14) 0.0471(11) 0.0061(10) 0.0025(10) -0.0011(12) C13 0.0702(16) 0.0630(16) 0.0548(13) 0.0022(11) 0.0065(11) 0.0051(13) C14 0.0762(17) 0.0776(18) 0.0467(12) -0.0030(12) 0.0075(11) -0.0102(15) C15 0.0662(16) 0.0775(18) 0.0515(13) 0.0161(12) -0.0057(11) -0.0042(14) C16 0.0723(18) 0.091(2) 0.0666(16) 0.0166(15) 0.0016(13) 0.0221(16) C17 0.0706(16) 0.0791(18) 0.0569(14) 0.0062(13) 0.0090(12) 0.0172(15) C18 0.0599(14) 0.0622(15) 0.0510(12) -0.0016(11) 0.0050(10) 0.0064(12) C19 0.0624(14) 0.0606(15) 0.0477(11) -0.0029(10) 0.0030(10) 0.0076(12) C20 0.0690(16) 0.0759(18) 0.0563(13) -0.0095(13) -0.0012(11) 0.0066(14) C21 0.0650(16) 0.0795(19) 0.0680(15) -0.0160(14) 0.0058(12) 0.0004(15) C22 0.0691(16) 0.0680(18) 0.0765(17) -0.0013(14) 0.0061(13) -0.0051(14) C23 0.0662(16) 0.0706(17) 0.0642(14) 0.0087(13) -0.0002(12) -0.0021(14) C24 0.0725(19) 0.105(3) 0.089(2) -0.0269(19) -0.0016(15) -0.0112(19) F1 0.1070(15) 0.1437(19) 0.0569(9) 0.0286(10) -0.0132(9) 0.0136(14) O1 0.0804(12) 0.0718(12) 0.0501(9) 0.0080(8) -0.0046(8) 0.0026(10) O2 0.1016(16) 0.0860(15) 0.0655(11) 0.0281(11) 0.0050(10) -0.0026(12) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C1 C2 116.7(2) O2 C1 C2 128.0(3) O2 C1 O1 115.3(2) C3 C2 C1 119.0(2) C11 C2 C1 120.2(2) C11 C2 C3 120.8(2) C2 C3 H3 115.4 C4 C3 C2 129.2(2) C4 C3 H3 115.4 C3 C4 H4 118.1 C3 C4 C5 123.8(2) C5 C4 H4 118.1 C6 C5 C4 123.2(3) C10 C5 C4 120.0(3) C10 C5 C6 116.8(3) C5 C6 H6 118.8 C7 C6 C5 122.3(3) C7 C6 H6 118.8 C6 C7 H7 119.9 C6 C7 C8 120.2(4) C8 C7 H7 119.9 C7 C8 H8 120.7 C9 C8 C7 118.7(3) C9 C8 H8 120.7 C8 C9 H9 120.0 C8 C9 C10 120.1(4) C10 C9 H9 120.0 C5 C10 H10 119.1 C9 C10 C5 121.8(3) C9 C10 H10 119.1 C2 C11 C12 121.4(2) C2 C11 C18 120.6(2) C18 C11 C12 118.0(2) C13 C12 C11 120.5(2) C13 C12 C17 118.8(2) C17 C12 C11 120.7(2) C12 C13 H13 119.2 C12 C13 C14 121.5(3) C14 C13 H13 119.2 C13 C14 H14 121.2 C15 C14 C13 117.6(3) C15 C14 H14 121.2 C16 C15 C14 123.0(2) C16 C15 F1 119.2(3) F1 C15 C14 117.8(3) C15 C16 H16 120.7 C15 C16 C17 118.6(3) C17 C16 H16 120.7 C12 C17 C16 120.5(3) C12 C17 H17 119.8 C16 C17 H17 119.8 C19 C18 C11 118.7(2) C19 C18 C23 116.6(2) C23 C18 C11 124.7(2) C18 C19 C20 122.2(3) O1 C19 C18 120.9(2) O1 C19 C20 116.9(2) C19 C20 H20 119.8 C21 C20 C19 120.4(2) C21 C20 H20 119.8 C20 C21 C22 118.3(3) C20 C21 C24 121.5(3) C22 C21 C24 120.2(3) C21 C22 H22 119.4 C23 C22 C21 121.2(3) C23 C22 H22 119.4 C18 C23 H23 119.4 C22 C23 C18 121.3(3) C22 C23 H23 119.4 C21 C24 H24A 109.5 C21 C24 H24B 109.5 C21 C24 H24C 109.5 H24A C24 H24B 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 C19 O1 C1 122.80(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.470(3) C1 O1 1.390(3) C1 O2 1.187(3) C2 C3 1.460(4) C2 C11 1.365(4) C3 H3 0.9300 C3 C4 1.342(4) C4 H4 0.9300 C4 C5 1.472(4) C5 C6 1.386(4) C5 C10 1.378(4) C6 H6 0.9300 C6 C7 1.353(5) C7 H7 0.9300 C7 C8 1.388(6) C8 H8 0.9300 C8 C9 1.375(6) C9 H9 0.9300 C9 C10 1.377(5) C10 H10 0.9300 C11 C12 1.503(3) C11 C18 1.441(4) C12 C13 1.372(4) C12 C17 1.380(4) C13 H13 0.9300 C13 C14 1.389(3) C14 H14 0.9300 C14 C15 1.361(4) C15 C16 1.355(4) C15 F1 1.359(3) C16 H16 0.9300 C16 C17 1.389(4) C17 H17 0.9300 C18 C19 1.384(3) C18 C23 1.405(4) C19 C20 1.394(4) C19 O1 1.373(3) C20 H20 0.9300 C20 C21 1.374(4) C21 C22 1.393(4) C21 C24 1.507(4) C22 H22 0.9300 C22 C23 1.376(4) C23 H23 0.9300 C24 H24A 0.9600 C24 H24B 0.9600 C24 H24C 0.9600 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 C1 C2 C3 C4 0.4(4) C1 C2 C11 C12 178.8(2) C1 C2 C11 C18 0.8(4) C2 C1 O1 C19 3.9(4) C2 C3 C4 C5 -175.2(3) C2 C11 C12 C13 -86.2(3) C2 C11 C12 C17 93.6(3) C2 C11 C18 C19 1.8(4) C2 C11 C18 C23 -178.1(3) C3 C2 C11 C12 0.5(4) C3 C2 C11 C18 -177.4(2) C3 C4 C5 C6 10.5(5) C3 C4 C5 C10 -170.8(3) C4 C5 C6 C7 178.5(3) C4 C5 C10 C9 -179.8(3) C5 C6 C7 C8 2.6(6) C6 C5 C10 C9 -1.1(5) C6 C7 C8 C9 -3.7(7) C7 C8 C9 C10 2.5(7) C8 C9 C10 C5 -0.1(6) C10 C5 C6 C7 -0.1(5) C11 C2 C3 C4 178.7(3) C11 C12 C13 C14 -179.9(3) C11 C12 C17 C16 -179.4(3) C11 C18 C19 C20 178.8(2) C11 C18 C19 O1 -1.7(4) C11 C18 C23 C22 -179.6(3) C12 C11 C18 C19 -176.2(2) C12 C11 C18 C23 3.8(4) C12 C13 C14 C15 -1.3(4) C13 C12 C17 C16 0.4(4) C13 C14 C15 C16 1.6(5) C13 C14 C15 F1 -179.7(3) C14 C15 C16 C17 -1.0(5) C15 C16 C17 C12 0.0(5) C17 C12 C13 C14 0.3(4) C18 C11 C12 C13 91.9(3) C18 C11 C12 C17 -88.4(3) C18 C19 C20 C21 1.1(4) C18 C19 O1 C1 -1.3(4) C19 C18 C23 C22 0.4(4) C19 C20 C21 C22 0.0(4) C19 C20 C21 C24 179.0(3) C20 C19 O1 C1 178.3(2) C20 C21 C22 C23 -0.9(5) C21 C22 C23 C18 0.7(5) C23 C18 C19 C20 -1.3(4) C23 C18 C19 O1 178.3(2) C24 C21 C22 C23 -179.9(3) F1 C15 C16 C17 -179.6(3) O1 C1 C2 C3 174.7(2) O1 C1 C2 C11 -3.6(4) O1 C19 C20 C21 -178.5(2) O2 C1 C2 C3 -5.6(4) O2 C1 C2 C11 176.1(3) O2 C1 O1 C19 -175.9(2)