#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:01:31 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257292 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557262.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_1557262 loop_ _publ_author_name 'Groves, Alistair' 'Sun, Jinwei' 'Parke, Hal R. I.' 'Callingham, Michael' 'Argent, Stephen P.' 'Taylor, Laurence J.' 'Lam, Hon Wai' _publ_section_title ; Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration ; _journal_issue 10 _journal_name_full 'Chemical Science' _journal_page_first 2759 _journal_page_last 2764 _journal_paper_doi 10.1039/C9SC06309A _journal_volume 11 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C21 H21 F O2' _chemical_formula_sum 'C21 H21 F O2' _chemical_formula_weight 324.38 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2019-07-15 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-10-17 deposited with the CCDC. 2020-02-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.502(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.5120(2) _cell_length_b 15.3360(3) _cell_length_c 8.7541(2) _cell_measurement_reflns_used 24403 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 74.2730 _cell_measurement_theta_min 2.8630 _cell_volume 813.41(4) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 120(2) _diffrn_crystal_treatment 'flash frozen in gaseous N2' _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 10.3613 _diffrn_detector_type 'Agilent Diffraction Atlas detector' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.995 _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 -50.00 34.00 1.00 1.00 -- -38.50 38.00 90.00 84 2 \w -93.00 -2.00 1.00 1.00 -- -38.50 125.00 -60.00 91 3 \w 1.00 83.00 1.00 1.00 -- 43.32 -99.00 -30.00 82 4 \w 31.00 91.00 1.00 4.00 -- 106.13 -30.00-150.00 60 5 \w 25.00 109.00 1.00 4.00 -- 106.13 -95.00 120.00 84 6 \w 31.00 91.00 1.00 4.00 -- 106.13 -30.00 60.00 60 7 \w 25.00 109.00 1.00 4.00 -- 106.13 -95.00 0.00 84 8 \w 35.00 117.00 1.00 4.00 -- 106.13-125.00 -30.00 82 9 \w 82.00 177.00 1.00 4.00 -- 106.13 45.00 120.00 95 10 \w 17.00 113.00 1.00 1.00 -- 43.32 57.00 60.00 96 11 \w 17.00 113.00 1.00 1.00 -- 43.32 57.00 -60.00 96 12 \w 79.00 176.00 1.00 4.00 -- 106.13 61.00 0.00 97 13 \w 61.00 178.00 1.00 4.00 -- 106.13 15.00 -30.00 117 14 \w 79.00 176.00 1.00 4.00 -- 106.13 61.00 60.00 97 15 \w 82.00 178.00 1.00 4.00 -- 106.13 30.00-150.00 96 16 \w -50.00 28.00 1.00 1.00 -- -38.50 38.00-150.00 78 17 \w 17.00 113.00 1.00 1.00 -- 43.32 57.00-180.00 96 18 \w 61.00 87.00 1.00 1.00 -- 43.38 38.00 120.00 26 19 \w 91.00 116.00 1.00 1.00 -- 43.38 38.00 120.00 25 20 \w 144.00 170.00 1.00 4.00 -- 106.13 61.00 90.00 26 21 \w 79.00 105.00 1.00 4.00 -- 106.13 61.00 90.00 26 22 \w 61.00 106.00 1.00 4.00 -- 106.13 -61.00 120.00 45 23 \w 95.00 132.00 1.00 4.00 -- 106.13 30.00 150.00 37 24 \w 137.00 165.00 1.00 4.00 -- 106.13 125.00 0.00 28 25 \w 97.00 123.00 1.00 4.00 -- 106.13 125.00 0.00 26 26 \w -112.00 -7.00 1.00 1.00 -- -38.50 -77.00 90.00 105 27 \w 21.00 116.00 1.00 1.00 -- 43.38 38.00 -60.00 95 28 \w 12.00 117.00 1.00 1.00 -- 43.38 77.00-150.00 105 29 \w 12.00 117.00 1.00 1.00 -- 43.38 77.00 90.00 105 30 \w 23.00 98.00 1.00 1.00 -- 43.38-125.00-120.00 75 31 \w -29.00 66.00 1.00 1.00 -- 43.38 -38.00 30.00 95 32 \w 12.00 117.00 1.00 1.00 -- 43.38 77.00 -30.00 105 33 \w 79.00 176.00 1.00 4.00 -- 106.13 61.00 -90.00 97 34 \w 25.00 109.00 1.00 4.00 -- 106.13 -95.00-150.00 84 35 \w 79.00 176.00 1.00 4.00 -- 106.13 61.00 30.00 97 36 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00 -60.00 103 37 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00 150.00 103 38 \w 79.00 176.00 1.00 4.00 -- 106.13 61.00 150.00 97 39 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00-180.00 103 40 \w 79.00 176.00 1.00 4.00 -- 106.13 61.00-120.00 97 41 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00-150.00 103 42 \w 79.00 176.00 1.00 4.00 -- 106.13 61.00 -60.00 97 43 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00 -30.00 103 44 \w 79.00 176.00 1.00 4.00 -- 106.13 61.00 120.00 97 45 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00 60.00 103 46 \w 35.00 98.00 1.00 4.00 -- 106.13 -45.00 -30.00 63 47 \w -75.00 40.00 1.00 1.00 -- -38.50 19.00 -30.00 115 48 \w -43.00 130.00 1.00 1.00 -- 43.38 0.00-150.00 173 49 \w 12.00 117.00 1.00 1.00 -- 43.38 77.00 0.00 105 50 \w -43.00 130.00 1.00 1.00 -- 43.38 0.00-180.00 173 51 \w -43.00 130.00 1.00 1.00 -- 43.38 0.00 -90.00 173 52 \w -43.00 130.00 1.00 1.00 -- 43.38 0.00-120.00 173 53 \w 21.00 116.00 1.00 1.00 -- 43.38 38.00 0.00 95 54 \w 82.00 177.00 1.00 4.00 -- 106.13 45.00-120.00 95 55 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00 90.00 103 56 \w 79.00 176.00 1.00 4.00 -- 106.13 61.00 -30.00 97 57 \w 35.00 117.00 1.00 4.00 -- 106.13-125.00 120.00 82 58 \w 82.00 177.00 1.00 4.00 -- 106.13 45.00 -30.00 95 59 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00 120.00 103 60 \w 79.00 176.00 1.00 4.00 -- 106.13 61.00-180.00 97 61 \w 82.00 177.00 1.00 4.00 -- 106.13 45.00 150.00 95 62 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00 30.00 103 63 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00-120.00 103 64 \w 82.00 177.00 1.00 4.00 -- 106.13 45.00 -60.00 95 65 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00 -90.00 103 66 \w 82.00 177.00 1.00 4.00 -- 106.13 45.00 0.00 95 67 \w 75.00 178.00 1.00 4.00 -- 106.13 77.00 0.00 103 68 \w -43.00 84.00 1.00 1.00 -- 43.38 0.00 -60.00 127 ; _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'SuperNova, Atlas' _diffrn_measurement_method '\w scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0309232000 _diffrn_orient_matrix_UB_12 0.0089661000 _diffrn_orient_matrix_UB_13 0.1823973000 _diffrn_orient_matrix_UB_21 -0.1682928000 _diffrn_orient_matrix_UB_22 -0.0737634000 _diffrn_orient_matrix_UB_23 -0.0198384000 _diffrn_orient_matrix_UB_31 0.1881130000 _diffrn_orient_matrix_UB_32 -0.0675807000 _diffrn_orient_matrix_UB_33 0.0459263000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_unetI/netI 0.0074 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 32574 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.496 _diffrn_reflns_theta_min 5.431 _diffrn_source 'microfocus sealed tube' _diffrn_source_type 'Agilent Diffraction microfocus tube' _exptl_absorpt_coefficient_mu 0.740 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.393 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light yellow' _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.324 _exptl_crystal_description block _exptl_crystal_F_000 344 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: pentane/dichloromethane' _exptl_crystal_size_max 0.496 _exptl_crystal_size_mid 0.443 _exptl_crystal_size_min 0.219 _refine_diff_density_max 0.186 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.046 _refine_ls_abs_structure_details ; Flack x determined using 1567 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.028(19) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 223 _refine_ls_number_reflns 3270 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.090 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0283 _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^)+(0.0482P)^2^+0.1303P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0735 _refine_ls_wR_factor_ref 0.0735 _reflns_Friedel_coverage 0.922 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.991 _reflns_number_gt 3269 _reflns_number_total 3270 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06309a2.cif _cod_data_source_block aghwla _cod_depositor_comments ;Adding full bibliography for 1557262--1557263.cif. Adding full bibliography for 1557262--1557263.cif. ; _cod_database_code 1557262 _nottingham_internal_coll_name AGHWLA _nottingham_internal_coll_number 17911 _nottingham_internal_coll_client AG/HWL _nottingham_internal_coll_type custom _nottingham_internal_coll_frame_method '\w scans' _nottingham_internal_coll_frame_time '1.00, 4.00' _nottingham_internal_coll_frame_width 1.00 _nottingham_internal_coll_user pczlt _nottingham_internal_coll_date 10/09/2018 _nottingham_internal_coll_location NOTTS _nottingham_internal_coll_instrument 'SN, XDA 017-09' _nottingham_internal_process_date 11/09/2018 _nottingham_internal_process_user pczlt _nottingham_internal_solution_date 15/07/2019 _nottingham_internal_solution_user pczlt _nottingham_internal_refinement_date 15/07/2019 _nottingham_internal_refinement_user pczspa _nottingham_internal_validation_date 15/07/2019 _nottingham_internal_validation_user pczspa _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C21 H21 F O2' _chemical_oxdiff_usercomment 'AGHWA #17911 IN A FOMBLIN FILM ON A MICROMOUNT FOR AG/HWL' _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 0.855 _shelx_estimated_absorpt_t_min 0.711 _reflns_odcompleteness_completeness 99.93 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 67.13 _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, All O(H) groups 2. Restrained distances O2-H2 0.82 with sigma of 0.02 3.a Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 3.b Aromatic/amide H refined with riding coordinates: C17(H17), C24(H24), C16(H16), C13(H13), C15(H15), C23(H23), C22(H22), C21(H21), C14(H14) 3.c Idealised Me refined as rotating group: C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C3(H3A,H3B,H3C) ; _shelx_res_file ; TITL aghwla_a.res in P2(1) aghwla.res created by SHELXL-2018/3 at 16:50:50 on 15-Jul-2019 REM Old TITL AGHWLA in P2(1) REM SHELXT solution in P2(1) REM R1 0.079, Rweak 0.034, Alpha 0.008, Orientation as input REM Flack x = 0.046 ( 0.022 ) from Parsons' quotients REM Formula found by SHELXT: C21 O2 F CELL 1.54184 6.512 15.336 8.7541 90 111.502 90 ZERR 2 0.0002 0.0003 0.0002 0 0.003 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O F UNIT 42 42 4 2 DFIX 0.82 O2 H2 L.S. 10 PLAN 5 SIZE 0.219 0.443 0.496 TEMP -153(2) HTAB O2 O6 BOND $H list 4 fmap 2 53 acta OMIT -2 0 5 OMIT 0 -2 0 OMIT 1 0 3 OMIT 0 2 0 OMIT 0 -2 1 OMIT 2 0 3 REM REM REM WGHT 0.048200 0.130300 FVAR 1.67027 F20 4 0.707082 0.645064 1.005637 11.00000 0.01552 0.03646 = 0.03021 -0.01467 0.00634 -0.00371 O2 3 0.601084 0.434734 0.192461 11.00000 0.03320 0.02659 = 0.01790 0.00110 0.01542 0.00320 H2 2 0.683890 0.478625 0.226727 11.00000 -1.50000 O6 3 0.728471 0.578246 0.376467 11.00000 0.02432 0.02529 = 0.03840 -0.00105 0.01495 -0.00545 C10 1 0.509833 0.469907 0.646201 11.00000 0.01497 0.01446 = 0.01472 0.00170 0.00656 -0.00160 C12 1 0.682057 0.387921 0.475257 11.00000 0.01711 0.01284 = 0.01778 0.00005 0.00738 -0.00248 C17 1 0.539239 0.510405 0.789134 11.00000 0.01562 0.01907 = 0.01490 0.00141 0.00534 0.00059 AFIX 43 H17 2 0.671933 0.496861 0.878034 11.00000 -1.20000 AFIX 0 C19 1 0.483403 0.640192 0.935469 11.00000 0.01475 0.02402 = 0.01786 -0.00047 0.00725 -0.00188 C24 1 0.160259 0.569848 0.758216 11.00000 0.01773 0.02570 = 0.01430 -0.00079 0.00691 -0.00267 AFIX 43 H24 2 0.088641 0.524074 0.684936 11.00000 -1.20000 AFIX 0 C16 1 0.840178 0.372146 0.769831 11.00000 0.02241 0.01912 = 0.01723 0.00133 0.00577 0.00198 AFIX 43 H16 2 0.838398 0.385113 0.875455 11.00000 -1.20000 AFIX 0 C11 1 0.679017 0.409246 0.630397 11.00000 0.01579 0.01318 = 0.01690 0.00066 0.00582 -0.00189 C18 1 0.391718 0.572972 0.824898 11.00000 0.01790 0.01859 = 0.01263 0.00189 0.00747 0.00041 C13 1 0.845161 0.331409 0.464142 11.00000 0.02506 0.02008 = 0.02217 -0.00071 0.01318 0.00095 AFIX 43 H13 2 0.846695 0.316866 0.359078 11.00000 -1.20000 AFIX 0 C1 1 0.506514 0.419178 0.314063 11.00000 0.02171 0.01784 = 0.01250 -0.00109 0.00695 -0.00082 C4 1 0.389180 0.502022 0.342618 11.00000 0.01569 0.01682 = 0.01269 0.00114 0.00442 -0.00023 C15 1 1.001318 0.317170 0.756670 11.00000 0.02217 0.02216 = 0.02413 0.00521 0.00486 0.00553 AFIX 43 H15 2 1.110205 0.293624 0.852659 11.00000 -1.20000 AFIX 0 C23 1 0.034497 0.632633 0.797749 11.00000 0.01703 0.03284 = 0.01690 0.00297 0.00729 0.00211 AFIX 43 H23 2 -0.121959 0.629791 0.749956 11.00000 -1.20000 AFIX 0 C9 1 0.315971 0.486580 0.489521 11.00000 0.01467 0.01913 = 0.01327 0.00024 0.00532 0.00015 AFIX 23 H9A 2 0.234129 0.538328 0.504119 11.00000 -1.20000 H9B 2 0.214771 0.435943 0.465694 11.00000 -1.20000 AFIX 0 C5 1 0.545813 0.581023 0.384311 11.00000 0.02187 0.01804 = 0.01479 0.00352 0.00602 -0.00034 C22 1 0.134504 0.699492 0.906216 11.00000 0.02666 0.02304 = 0.02215 0.00367 0.01424 0.00825 AFIX 43 H22 2 0.046918 0.742420 0.931794 11.00000 -1.20000 AFIX 0 C21 1 0.362891 0.703443 0.977210 11.00000 0.02781 0.01919 = 0.02345 -0.00394 0.01297 -0.00227 AFIX 43 H21 2 0.434249 0.748471 1.052479 11.00000 -1.20000 AFIX 0 C14 1 1.003585 0.296445 0.602635 11.00000 0.02219 0.02333 = 0.03295 0.00317 0.01392 0.00651 AFIX 43 H14 2 1.113392 0.258495 0.592814 11.00000 -1.20000 AFIX 0 C7 1 0.467988 0.664419 0.435690 11.00000 0.03626 0.01662 = 0.03124 -0.00098 0.01274 0.00142 AFIX 137 H7A 2 0.458918 0.656677 0.544162 11.00000 -1.50000 H7B 2 0.321942 0.679577 0.355744 11.00000 -1.50000 H7C 2 0.572392 0.711344 0.440642 11.00000 -1.50000 AFIX 0 C8 1 0.184444 0.524998 0.190555 11.00000 0.02055 0.03046 = 0.01451 0.00323 0.00292 0.00321 AFIX 137 H8A 2 0.224113 0.525163 0.092843 11.00000 -1.50000 H8B 2 0.130350 0.582853 0.205096 11.00000 -1.50000 H8C 2 0.068614 0.481596 0.176982 11.00000 -1.50000 AFIX 0 C3 1 0.344452 0.344203 0.241817 11.00000 0.02824 0.02177 = 0.02155 -0.00558 0.00341 -0.00348 AFIX 137 H3A 2 0.241804 0.360421 0.132111 11.00000 -1.50000 H3B 2 0.261485 0.332374 0.313032 11.00000 -1.50000 H3C 2 0.426389 0.291849 0.234088 11.00000 -1.50000 AFIX 0 HKLF 4 REM aghwla_a.res in P2(1) REM wR2 = 0.0735, GooF = S = 1.090, Restrained GooF = 1.090 for all data REM R1 = 0.0283 for 3269 Fo > 4sig(Fo) and 0.0283 for all 3270 data REM 223 parameters refined using 2 restraints END WGHT 0.0482 0.1303 REM Highest difference peak 0.186, deepest hole -0.211, 1-sigma level 0.046 Q1 1 0.4439 0.4609 0.3256 11.00000 0.05 0.19 Q2 1 0.5880 0.4057 0.3988 11.00000 0.05 0.16 Q3 1 0.4164 0.3829 0.2835 11.00000 0.05 0.14 Q4 1 0.3285 0.6628 0.4587 11.00000 0.05 0.14 Q5 1 0.4351 0.5542 0.1061 11.00000 0.05 0.14 ; _shelx_res_checksum 3880 _olex2_date_sample_submission 2018-09-06 _olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount' _olex2_submission_original_sample_id AGHWLA _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 1.331 _oxdiff_exptl_absorpt_empirical_full_min 0.829 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn F20 F 0.70708(16) 0.64506(8) 1.00564(14) 0.0280(3) Uani 1 1 d . O2 O 0.6011(2) 0.43473(9) 0.19246(16) 0.0242(3) Uani 1 1 d D H2 H 0.684(4) 0.4786(16) 0.227(3) 0.036 Uiso 1 1 d DR O6 O 0.7285(2) 0.57825(9) 0.37647(18) 0.0284(3) Uani 1 1 d . C10 C 0.5098(3) 0.46991(10) 0.6462(2) 0.0144(3) Uani 1 1 d . C12 C 0.6821(3) 0.38792(10) 0.4753(2) 0.0156(3) Uani 1 1 d . C17 C 0.5392(3) 0.51040(11) 0.7891(2) 0.0166(3) Uani 1 1 d . H17 H 0.671933 0.496861 0.878034 0.020 Uiso 1 1 calc R C19 C 0.4834(3) 0.64019(12) 0.9355(2) 0.0185(3) Uani 1 1 d . C24 C 0.1603(3) 0.56985(12) 0.7582(2) 0.0190(3) Uani 1 1 d . H24 H 0.088641 0.524074 0.684936 0.023 Uiso 1 1 calc R C16 C 0.8402(3) 0.37215(12) 0.7698(2) 0.0200(3) Uani 1 1 d . H16 H 0.838398 0.385113 0.875455 0.024 Uiso 1 1 calc R C11 C 0.6790(3) 0.40925(10) 0.6304(2) 0.0153(3) Uani 1 1 d . C18 C 0.3917(3) 0.57297(11) 0.82490(19) 0.0158(3) Uani 1 1 d . C13 C 0.8452(3) 0.33141(11) 0.4641(2) 0.0212(4) Uani 1 1 d . H13 H 0.846695 0.316866 0.359078 0.025 Uiso 1 1 calc R C1 C 0.5065(3) 0.41918(11) 0.3141(2) 0.0172(3) Uani 1 1 d . C4 C 0.3892(3) 0.50202(10) 0.3426(2) 0.0153(3) Uani 1 1 d . C15 C 1.0013(3) 0.31717(12) 0.7567(2) 0.0238(4) Uani 1 1 d . H15 H 1.110205 0.293624 0.852659 0.029 Uiso 1 1 calc R C23 C 0.0345(3) 0.63263(13) 0.7977(2) 0.0220(4) Uani 1 1 d . H23 H -0.121959 0.629791 0.749956 0.026 Uiso 1 1 calc R C9 C 0.3160(3) 0.48658(11) 0.48952(19) 0.0156(3) Uani 1 1 d . H9A H 0.234129 0.538328 0.504119 0.019 Uiso 1 1 calc R H9B H 0.214771 0.435943 0.465694 0.019 Uiso 1 1 calc R C5 C 0.5458(3) 0.58102(11) 0.3843(2) 0.0184(3) Uani 1 1 d . C22 C 0.1345(3) 0.69949(12) 0.9062(2) 0.0225(4) Uani 1 1 d . H22 H 0.046918 0.742420 0.931794 0.027 Uiso 1 1 calc R C21 C 0.3629(3) 0.70344(12) 0.9772(2) 0.0225(4) Uani 1 1 d . H21 H 0.434249 0.748471 1.052479 0.027 Uiso 1 1 calc R C14 C 1.0036(3) 0.29645(12) 0.6026(3) 0.0251(4) Uani 1 1 d . H14 H 1.113392 0.258495 0.592814 0.030 Uiso 1 1 calc R C7 C 0.4680(4) 0.66442(12) 0.4357(3) 0.0279(4) Uani 1 1 d . H7A H 0.458918 0.656677 0.544162 0.042 Uiso 1 1 calc GR H7B H 0.321942 0.679577 0.355744 0.042 Uiso 1 1 calc GR H7C H 0.572392 0.711344 0.440642 0.042 Uiso 1 1 calc GR C8 C 0.1844(3) 0.52500(13) 0.1906(2) 0.0228(4) Uani 1 1 d . H8A H 0.224113 0.525163 0.092843 0.034 Uiso 1 1 calc GR H8B H 0.130350 0.582853 0.205096 0.034 Uiso 1 1 calc GR H8C H 0.068614 0.481596 0.176982 0.034 Uiso 1 1 calc GR C3 C 0.3445(3) 0.34420(12) 0.2418(2) 0.0255(4) Uani 1 1 d . H3A H 0.241804 0.360421 0.132111 0.038 Uiso 1 1 calc GR H3B H 0.261485 0.332374 0.313032 0.038 Uiso 1 1 calc GR H3C H 0.426389 0.291849 0.234088 0.038 Uiso 1 1 calc GR 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 F20 0.0155(5) 0.0365(6) 0.0302(6) -0.0147(5) 0.0063(4) -0.0037(4) O2 0.0332(7) 0.0266(7) 0.0179(6) 0.0011(5) 0.0154(5) 0.0032(5) O6 0.0243(7) 0.0253(7) 0.0384(8) -0.0010(6) 0.0150(6) -0.0054(5) C10 0.0150(7) 0.0145(7) 0.0147(7) 0.0017(6) 0.0066(6) -0.0016(6) C12 0.0171(7) 0.0128(7) 0.0178(7) 0.0000(6) 0.0074(6) -0.0025(6) C17 0.0156(7) 0.0191(7) 0.0149(7) 0.0014(6) 0.0053(6) 0.0006(6) C19 0.0147(7) 0.0240(9) 0.0179(7) -0.0005(6) 0.0073(6) -0.0019(7) C24 0.0177(8) 0.0257(9) 0.0143(7) -0.0008(6) 0.0069(6) -0.0027(6) C16 0.0224(8) 0.0191(8) 0.0172(8) 0.0013(6) 0.0058(7) 0.0020(6) C11 0.0158(7) 0.0132(7) 0.0169(7) 0.0007(6) 0.0058(6) -0.0019(6) C18 0.0179(8) 0.0186(8) 0.0126(7) 0.0019(6) 0.0075(6) 0.0004(6) C13 0.0251(9) 0.0201(9) 0.0222(8) -0.0007(7) 0.0132(7) 0.0009(7) C1 0.0217(8) 0.0178(8) 0.0125(7) -0.0011(6) 0.0069(6) -0.0008(6) C4 0.0157(7) 0.0168(8) 0.0127(7) 0.0011(6) 0.0044(6) -0.0002(6) C15 0.0222(9) 0.0222(9) 0.0241(9) 0.0052(7) 0.0049(7) 0.0055(7) C23 0.0170(8) 0.0328(9) 0.0169(8) 0.0030(7) 0.0073(6) 0.0021(7) C9 0.0147(7) 0.0191(8) 0.0133(7) 0.0002(6) 0.0053(6) 0.0001(6) C5 0.0219(8) 0.0180(8) 0.0148(7) 0.0035(6) 0.0060(6) -0.0003(6) C22 0.0267(9) 0.0230(8) 0.0221(8) 0.0037(7) 0.0142(7) 0.0082(7) C21 0.0278(9) 0.0192(8) 0.0234(9) -0.0039(7) 0.0130(7) -0.0023(7) C14 0.0222(9) 0.0233(9) 0.0330(10) 0.0032(7) 0.0139(8) 0.0065(7) C7 0.0363(10) 0.0166(8) 0.0312(10) -0.0010(7) 0.0127(8) 0.0014(7) C8 0.0205(8) 0.0305(9) 0.0145(7) 0.0032(7) 0.0029(7) 0.0032(7) C3 0.0282(9) 0.0218(8) 0.0215(8) -0.0056(7) 0.0034(7) -0.0035(7) 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' O O 0.0492 0.0322 '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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 4 2 -2 0.2369 3 -6 0 0.2145 -1 -9 1 0.2412 -4 1 1 0.1927 0 -1 -5 0.1116 1 -1 5 0.1005 -1 3 5 0.1037 1 -2 -6 0.1197 3 -7 -3 0.2258 0 10 1 0.1947 3 5 2 0.2002 4 0 1 0.1995 0 7 -4 0.1899 4 0 -5 0.1950 0 -6 4 0.1738 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O2 H2 105(2) C17 C10 C11 121.16(14) C17 C10 C9 123.64(15) C11 C10 C9 115.06(13) C11 C12 C1 123.23(14) C13 C12 C11 119.40(15) C13 C12 C1 117.28(15) C10 C17 H17 115.9 C10 C17 C18 128.13(15) C18 C17 H17 115.9 F20 C19 C18 118.09(14) F20 C19 C21 117.47(15) C21 C19 C18 124.43(16) C18 C24 H24 119.5 C23 C24 H24 119.5 C23 C24 C18 120.97(16) C11 C16 H16 119.3 C15 C16 H16 119.3 C15 C16 C11 121.47(16) C12 C11 C10 120.63(14) C12 C11 C16 118.35(15) C16 C11 C10 121.02(15) C19 C18 C17 119.00(14) C19 C18 C24 115.89(15) C24 C18 C17 125.10(15) C12 C13 H13 119.3 C14 C13 C12 121.38(16) C14 C13 H13 119.3 O2 C1 C12 110.98(13) O2 C1 C4 110.81(13) O2 C1 C3 103.72(13) C12 C1 C4 110.71(13) C12 C1 C3 108.31(14) C3 C1 C4 112.10(14) C9 C4 C1 109.24(13) C5 C4 C1 111.14(13) C5 C4 C9 107.65(13) C5 C4 C8 108.26(13) C8 C4 C1 111.71(13) C8 C4 C9 108.72(13) C16 C15 H15 120.1 C16 C15 C14 119.87(17) C14 C15 H15 120.1 C24 C23 H23 119.6 C22 C23 C24 120.78(16) C22 C23 H23 119.6 C10 C9 C4 111.87(13) C10 C9 H9A 109.2 C10 C9 H9B 109.2 C4 C9 H9A 109.2 C4 C9 H9B 109.2 H9A C9 H9B 107.9 O6 C5 C4 122.38(16) O6 C5 C7 119.34(16) C7 C5 C4 118.27(15) C23 C22 H22 120.1 C23 C22 C21 119.76(16) C21 C22 H22 120.1 C19 C21 C22 118.13(16) C19 C21 H21 120.9 C22 C21 H21 120.9 C13 C14 C15 119.52(16) C13 C14 H14 120.2 C15 C14 H14 120.2 C5 C7 H7A 109.5 C5 C7 H7B 109.5 C5 C7 H7C 109.5 H7A C7 H7B 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 C4 C8 H8A 109.5 C4 C8 H8B 109.5 C4 C8 H8C 109.5 H8A C8 H8B 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C1 C3 H3A 109.5 C1 C3 H3B 109.5 C1 C3 H3C 109.5 H3A C3 H3B 109.5 H3A C3 H3C 109.5 H3B C3 H3C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F20 C19 1.3597(19) O2 H2 0.85(2) O2 C1 1.432(2) O6 C5 1.217(2) C10 C17 1.346(2) C10 C11 1.487(2) C10 C9 1.507(2) C12 C11 1.404(2) C12 C13 1.402(2) C12 C1 1.531(2) C17 H17 0.9500 C17 C18 1.470(2) C19 C18 1.390(2) C19 C21 1.379(2) C24 H24 0.9500 C24 C18 1.404(2) C24 C23 1.388(3) C16 H16 0.9500 C16 C11 1.406(2) C16 C15 1.383(3) C13 H13 0.9500 C13 C14 1.380(3) C1 C4 1.549(2) C1 C3 1.532(2) C4 C9 1.545(2) C4 C5 1.539(2) C4 C8 1.540(2) C15 H15 0.9500 C15 C14 1.391(3) C23 H23 0.9500 C23 C22 1.387(3) C9 H9A 0.9900 C9 H9B 0.9900 C5 C7 1.504(3) C22 H22 0.9500 C22 C21 1.387(3) C21 H21 0.9500 C14 H14 0.9500 C7 H7A 0.9800 C7 H7B 0.9800 C7 H7C 0.9800 C8 H8A 0.9800 C8 H8B 0.9800 C8 H8C 0.9800 C3 H3A 0.9800 C3 H3B 0.9800 C3 H3C 0.9800 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O2 H2 O6 0.85(2) 1.96(3) 2.673(2) 141(3) yes loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 3.9967 2.0028 -1.9956 -0.2225 -0.7808 0.5248 2.9969 -5.9965 0.0007 0.0390 -0.0621 0.9690 -0.9993 -8.9979 0.9963 0.0701 0.8121 0.4659 -3.9963 0.9971 0.9968 0.0672 0.5792 -0.7734 0.0024 -0.9944 -4.9991 -0.9207 0.1721 -0.1619 0.9966 -1.0044 4.9993 0.9337 -0.1928 0.4849 -1.0014 2.9932 4.9988 0.9076 -0.1514 -0.1611 1.0019 -1.9926 -5.9983 -1.0810 0.0974 0.0476 2.9984 -6.9930 -2.9989 -0.5170 0.0707 0.8989 -0.0006 9.9950 1.0027 0.2725 -0.7571 -0.6295 2.9958 4.9971 2.0034 0.5029 -0.9125 0.3179 3.9953 0.0004 1.0030 0.3065 -0.6923 0.7976 0.0018 7.0014 -3.9970 -0.6662 -0.4375 -0.6564 3.9982 0.0067 -4.9955 -0.7875 -0.5743 0.5222 -0.0018 -6.0018 3.9972 0.6752 0.3637 0.5888