#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:01:38 +0300 (Fri, 01 May 2020) $ #$Revision: 251333 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126469.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_7126469 loop_ _publ_author_name 'Tang, Pan-Ting' 'Wang, Liang-Neng' 'Shao, Youxiang' 'Wei, Yi' 'Li, Ming' 'Zhang, Ni-Juan' 'Luo, Xiao-Peng' 'Ke, Zhuofeng' 'Liu, Yue-Jin' 'Zeng, Ming-Hua' _publ_section_title ; Synthesis of seven-membered lactones by regioselective and stereoselective iodolactonization of electron-deficient olefins ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC10080F _journal_year 2020 _chemical_absolute_configuration S _chemical_formula_moiety 'C19 H14 F3 I O4' _chemical_formula_sum 'C19 H14 F3 I O4' _chemical_formula_weight 490.20 _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-06-14 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-12-23 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.504(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.2645(2) _cell_length_b 22.2327(6) _cell_length_c 18.2492(5) _cell_measurement_reflns_used 14088 _cell_measurement_temperature 99.99(10) _cell_measurement_theta_max 30.2730 _cell_measurement_theta_min 2.1370 _cell_volume 3683.36(17) _computing_cell_refinement 'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)' _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 99.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.881 _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 3.00 84.00 0.50 3.06 -- 10.14 57.00 -90.00 162 2 \w -12.00 81.00 0.50 3.06 -- 10.14 57.00 90.00 186 3 \w -26.00 -1.00 0.50 3.06 -- -9.05 -99.00 30.00 50 4 \w -24.00 28.00 0.50 3.06 -- 10.14 -99.00 90.00 104 5 \w 33.00 59.00 0.50 3.06 -- 10.14-143.00 89.00 52 6 \w -26.00 15.00 0.50 3.06 -- -9.05 -99.00 -90.00 82 7 \w 11.00 54.00 0.50 3.06 -- 10.14-127.00-100.00 86 8 \w -25.00 42.00 0.50 3.06 -- 10.14 -99.00 -30.00 134 9 \w -24.00 46.00 0.50 3.06 -- 10.14 -99.00 -60.00 140 10 \w -13.00 48.00 0.50 3.06 -- 10.14 -99.00 120.00 122 11 \w -73.00 -31.00 0.50 3.06 -- -9.05 -57.00-180.00 84 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0606674000 _diffrn_orient_matrix_UB_12 0.0148044000 _diffrn_orient_matrix_UB_13 0.0226757000 _diffrn_orient_matrix_UB_21 0.0294529000 _diffrn_orient_matrix_UB_22 -0.0282118000 _diffrn_orient_matrix_UB_23 0.0136900000 _diffrn_orient_matrix_UB_31 0.0394532000 _diffrn_orient_matrix_UB_32 -0.0017124000 _diffrn_orient_matrix_UB_33 -0.0294997000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0755 _diffrn_reflns_av_unetI/netI 0.0586 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.881 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 28911 _diffrn_reflns_point_group_measured_fraction_full 0.975 _diffrn_reflns_point_group_measured_fraction_max 0.796 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.345 _diffrn_reflns_theta_min 2.157 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.790 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.54322 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.768 _exptl_crystal_description block _exptl_crystal_F_000 1920 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 2.060 _refine_diff_density_min -1.779 _refine_diff_density_rms 0.147 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.09(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 492 _refine_ls_number_reflns 8822 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.003 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0494 _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^)+(0.0867P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1195 _refine_ls_wR_factor_ref 0.1251 _reflns_Friedel_coverage 0.804 _reflns_Friedel_fraction_full 0.951 _reflns_Friedel_fraction_max 0.711 _reflns_number_gt 7925 _reflns_number_total 8822 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc10080f2.cif _cod_data_source_block tpt-14-10 _cod_database_code 7126469 _shelx_shelxl_version_number 2018/3 _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 0.716 _shelx_estimated_absorpt_t_min 0.716 _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.91(3) 0.09(3) 2. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 3.a Ternary CH refined with riding coordinates: C00O(H00O), C012(H012), C01A(H01A), C01C(H01H) 3.b Aromatic/amide H refined with riding coordinates: C00F(H00F), C00N(H00N), C00X(H00X), C00Z(H00Z), C013(H013), C014(H014), C015(H015), C016(H016), C018(H018), C019(H019), C01G(H01L), C01H(H01M) 3.c Idealised Me refined as rotating group: C00J(H00A,H00B,H00C), C01B(H01E,H01F,H01G), C01E(H01I,H01J,H01K), C01F(H01B, H01C,H01D) ; _shelx_res_file ; TITL tpt-14-10_a.res in Cc tpt-14-10.res created by SHELXL-2018/3 at 18:20:06 on 14-Jun-2019 REM Old TITL tpt-14-10_a.res in Cc REM SHELXT solution in Cc: R1 0.084, Rweak 0.013, Alpha 0.007 REM 0.817 for 101 systematic absences, Orientation as input REM Flack x = 0.098 ( 0.045 ) from 3107 Parsons' quotients REM Formula found by SHELXT: C37 N4 O11 I2 CELL 0.71073 9.2645 22.2327 18.2492 90 101.504 90 ZERR 8 0.0002 0.0006 0.0005 0 0.003 0 LATT -7 SYMM +X,-Y,0.5+Z SFAC C H F I O UNIT 152 112 24 8 32 L.S. 4 0 0 PLAN 20 SIZE 0.2 0.2 0.2 BOND list 4 fmap 2 53 ACTA TWIN -1 0 0 0 -1 0 0 0 -1 2 OMIT -4 20 3 OMIT -7 17 7 REM REM REM WGHT 0.086700 BASF 0.09096 FVAR 0.13079 I001 4 0.901380 0.566185 0.420459 11.00000 0.02492 0.02527 = 0.03307 -0.00061 0.00833 -0.00178 I002 4 0.100570 0.688118 0.580281 11.00000 0.02350 0.02461 = 0.03437 0.00133 0.00754 -0.00109 F003 3 -0.067046 0.685063 0.289788 11.00000 0.03336 0.04819 = 0.04494 -0.00700 -0.00066 -0.00676 O004 5 0.542146 0.693584 0.539390 11.00000 0.02309 0.01552 = 0.03754 0.00179 0.00237 0.00410 F005 3 0.103085 0.619317 0.290917 11.00000 0.05329 0.03154 = 0.04717 -0.00534 0.00296 0.00098 O006 5 0.461324 0.558085 0.459870 11.00000 0.01803 0.01279 = 0.04552 0.00012 0.01101 0.00060 O007 5 0.405849 0.585136 0.657739 11.00000 0.04463 0.01452 = 0.03564 0.00562 -0.00225 -0.00049 F008 3 0.900549 0.624218 0.710697 11.00000 0.06384 0.03372 = 0.04676 -0.01249 0.00489 -0.01467 O009 5 0.770607 0.718548 0.547370 11.00000 0.02271 0.02256 = 0.06801 -0.00145 0.00697 0.00348 F00A 3 0.923710 0.551374 0.787725 11.00000 0.10916 0.06215 = 0.02442 0.00274 0.00018 -0.03799 F00B 3 0.076499 0.692178 0.211361 11.00000 0.08451 0.04924 = 0.02741 -0.00319 0.00871 -0.01766 O00C 5 0.596145 0.667575 0.342447 11.00000 0.04602 0.01571 = 0.03224 -0.00049 -0.00154 -0.00152 O00D 5 0.549511 0.572154 0.306723 11.00000 0.06467 0.02051 = 0.03518 -0.00382 -0.00973 -0.00106 O00E 5 0.452986 0.680446 0.692428 11.00000 0.06332 0.02367 = 0.03906 0.00423 -0.01721 -0.00512 C00F 1 0.693191 0.437386 0.627876 11.00000 0.04202 0.02214 = 0.02936 0.00640 0.00642 -0.00448 AFIX 43 H00F 2 0.668577 0.398716 0.640471 11.00000 -1.20000 AFIX 0 O00G 5 0.230778 0.530197 0.452051 11.00000 0.02383 0.02205 = 0.05973 0.00279 0.00934 0.00483 C00H 1 0.072444 0.678938 0.282226 11.00000 0.04011 0.03257 = 0.02829 -0.00433 0.00145 -0.00144 F00I 3 1.070508 0.559656 0.709787 11.00000 0.03650 0.07098 = 0.08561 -0.01803 -0.00913 -0.00580 C00J 1 0.527340 0.686380 0.267871 11.00000 0.05127 0.02639 = 0.04465 0.00387 -0.00093 0.00352 AFIX 137 H00A 2 0.596202 0.682210 0.235246 11.00000 -1.50000 H00B 2 0.497551 0.727680 0.268875 11.00000 -1.50000 H00C 2 0.442547 0.661747 0.249939 11.00000 -1.50000 AFIX 0 C00K 1 0.528159 0.424314 0.502394 11.00000 0.02268 0.01883 = 0.03097 0.00212 0.00363 -0.00149 C00L 1 0.632714 0.460280 0.556346 11.00000 0.02575 0.01879 = 0.02756 0.00599 0.00896 -0.00237 C00M 1 0.401245 0.449765 0.455997 11.00000 0.01851 0.01724 = 0.03216 0.00400 0.00420 -0.00063 C00N 1 0.229876 0.695025 0.408134 11.00000 0.02452 0.01966 = 0.02707 0.00014 0.00796 -0.00348 AFIX 43 H00N 2 0.202557 0.657172 0.422272 11.00000 -1.20000 AFIX 0 C00O 1 0.390972 0.711994 0.537663 11.00000 0.02100 0.01202 = 0.02944 0.00093 0.00511 -0.00047 AFIX 13 H00O 2 0.391930 0.746811 0.570689 11.00000 -1.20000 AFIX 0 C00P 1 0.677391 0.517161 0.537971 11.00000 0.02510 0.01960 = 0.02519 -0.00038 0.00598 -0.00194 C00Q 1 0.324559 0.730845 0.459013 11.00000 0.02103 0.01902 = 0.02531 0.00112 0.00536 -0.00151 C00R 1 0.357430 0.514392 0.456897 11.00000 0.02461 0.01593 = 0.03258 0.00379 0.00585 0.00158 C00S 1 0.603280 0.800968 0.536281 11.00000 0.02585 0.01668 = 0.03170 0.00428 0.00692 0.00008 C00T 1 0.475333 0.824647 0.490006 11.00000 0.01879 0.01994 = 0.03519 0.00357 0.00523 -0.00125 C00U 1 0.369250 0.787388 0.437564 11.00000 0.01884 0.02269 = 0.03372 0.00082 0.00149 0.00185 C00V 1 0.646285 0.735628 0.540667 11.00000 0.02167 0.02408 = 0.03416 -0.00361 0.00285 0.00299 C00W 1 0.330365 0.351469 0.401021 11.00000 0.03048 0.02552 = 0.03602 0.00012 0.00843 -0.00106 C00X 1 0.303262 0.412734 0.407654 11.00000 0.02410 0.02149 = 0.03133 0.00267 0.00247 0.00069 AFIX 43 H00X 2 0.218080 0.429390 0.379291 11.00000 -1.20000 AFIX 0 C00Y 1 0.176537 0.716094 0.336276 11.00000 0.02683 0.03509 = 0.02929 -0.00012 0.00696 0.00605 C00Z 1 0.787429 0.471017 0.679102 11.00000 0.04149 0.03915 = 0.02853 0.00551 0.00675 -0.00193 AFIX 43 H00Z 2 0.825419 0.455240 0.726197 11.00000 -1.20000 AFIX 0 C010 1 0.601354 0.608220 0.352293 11.00000 0.02752 0.01874 = 0.02746 0.00102 0.00001 -0.00115 C011 1 0.400680 0.643881 0.646853 11.00000 0.02697 0.01692 = 0.03143 0.00030 0.00391 -0.00291 C012 1 0.612259 0.539575 0.460327 11.00000 0.01751 0.01720 = 0.03175 0.00214 0.00483 0.00289 AFIX 13 H012 2 0.610137 0.506145 0.425127 11.00000 -1.20000 AFIX 0 C013 1 0.772151 0.551744 0.590295 11.00000 0.02755 0.01984 = 0.03306 -0.00177 0.00869 -0.00534 AFIX 43 H013 2 0.798858 0.590176 0.577886 11.00000 -1.20000 AFIX 0 C014 1 0.454782 0.886823 0.492053 11.00000 0.02762 0.02000 = 0.04403 0.00961 0.00578 0.00101 AFIX 43 H014 2 0.373547 0.903905 0.460787 11.00000 -1.20000 AFIX 0 C015 1 0.703038 0.839859 0.580516 11.00000 0.02579 0.01776 = 0.03118 0.00399 0.00585 -0.00052 AFIX 43 H015 2 0.790020 0.824109 0.608204 11.00000 -1.20000 AFIX 0 C016 1 0.549620 0.362537 0.496133 11.00000 0.02781 0.01764 = 0.04003 0.00131 0.00117 0.00154 AFIX 43 H016 2 0.630714 0.344600 0.526527 11.00000 -1.20000 AFIX 0 C017 1 0.676824 0.901241 0.584580 11.00000 0.03211 0.01921 = 0.03480 0.00082 0.01195 -0.00487 C018 1 0.454295 0.327262 0.446272 11.00000 0.04027 0.01936 = 0.04509 0.00679 0.01295 0.00512 AFIX 43 H018 2 0.473752 0.286417 0.443027 11.00000 -1.20000 AFIX 0 C019 1 0.217537 0.773183 0.315024 11.00000 0.02664 0.03506 = 0.03102 0.00554 0.00076 0.00158 AFIX 43 H019 2 0.178904 0.787662 0.267334 11.00000 -1.20000 AFIX 0 C01A 1 0.684050 0.593457 0.430651 11.00000 0.02280 0.01606 = 0.02675 -0.00214 0.00576 -0.00303 AFIX 13 H01A 2 0.687442 0.628211 0.463984 11.00000 -1.20000 AFIX 0 C01B 1 0.781749 0.941144 0.637382 11.00000 0.04225 0.02161 = 0.04133 -0.00165 0.00311 -0.00882 AFIX 137 H01E 2 0.736951 0.952972 0.678267 11.00000 -1.50000 H01F 2 0.803835 0.976296 0.611114 11.00000 -1.50000 H01G 2 0.871070 0.919494 0.656286 11.00000 -1.50000 AFIX 0 C01C 1 0.316407 0.659833 0.569212 11.00000 0.02204 0.01901 = 0.03073 0.00129 0.00619 -0.00171 AFIX 13 H01H 2 0.309955 0.624847 0.536049 11.00000 -1.20000 AFIX 0 C01D 1 0.826605 0.528578 0.661111 11.00000 0.03234 0.03580 = 0.02778 -0.00364 0.00743 -0.00572 C01E 1 0.478589 0.566163 0.731973 11.00000 0.05921 0.02842 = 0.03095 0.00901 -0.00050 -0.00033 AFIX 137 H01I 2 0.478977 0.523036 0.734585 11.00000 -1.50000 H01J 2 0.426807 0.582165 0.768247 11.00000 -1.50000 H01K 2 0.578135 0.580730 0.742227 11.00000 -1.50000 AFIX 0 C01F 1 0.227724 0.312284 0.346286 11.00000 0.03815 0.04010 = 0.04112 -0.00538 0.00196 -0.00618 AFIX 137 H01B 2 0.132856 0.311077 0.359873 11.00000 -1.50000 H01C 2 0.267200 0.272297 0.347381 11.00000 -1.50000 H01D 2 0.217889 0.328577 0.296820 11.00000 -1.50000 AFIX 0 C01G 1 0.551293 0.923528 0.539007 11.00000 0.03797 0.01491 = 0.04419 0.00132 0.01232 -0.00216 AFIX 43 H01L 2 0.531353 0.964481 0.540049 11.00000 -1.20000 AFIX 0 C01H 1 0.315106 0.808079 0.364587 11.00000 0.02962 0.02276 = 0.03906 0.00872 0.00216 -0.00039 AFIX 43 H01M 2 0.344879 0.845269 0.349579 11.00000 -1.20000 AFIX 0 C01I 1 0.931432 0.564793 0.717147 11.00000 0.04320 0.04414 = 0.02655 -0.00296 0.00429 -0.01467 HKLF 4 REM tpt-14-10_a.res in Cc REM wR2 = 0.1251, GooF = S = 1.003, Restrained GooF = 1.003 for all data REM R1 = 0.0494 for 7925 Fo > 4sig(Fo) and 0.0554 for all 8822 data REM 492 parameters refined using 2 restraints END WGHT 0.0867 0.0000 REM Highest difference peak 2.060, deepest hole -1.779, 1-sigma level 0.147 Q1 1 0.5987 0.6811 0.5800 11.00000 0.05 2.06 Q2 1 0.4031 0.5599 0.4202 11.00000 0.05 1.98 Q3 1 0.9262 0.5628 0.4792 11.00000 0.05 1.36 Q4 1 0.2013 0.6831 0.5820 11.00000 0.05 1.28 Q5 1 0.9517 0.5628 0.3818 11.00000 0.05 1.27 Q6 1 0.8017 0.5632 0.4172 11.00000 0.05 1.26 Q7 1 0.0773 0.6862 0.5185 11.00000 0.05 1.19 Q8 1 1.0160 0.5633 0.4373 11.00000 0.05 1.16 Q9 1 0.1289 0.6834 0.6418 11.00000 0.05 1.14 Q10 1 0.8608 0.5628 0.4598 11.00000 0.05 1.13 Q11 1 -0.0134 0.6853 0.5637 11.00000 0.05 1.12 Q12 1 0.0449 0.6852 0.6184 11.00000 0.05 1.10 Q13 1 0.8781 0.5642 0.3570 11.00000 0.05 1.09 Q14 1 0.1535 0.6852 0.5417 11.00000 0.05 0.98 Q15 1 0.6001 0.9426 0.5802 11.00000 0.05 0.71 Q16 1 0.1905 0.6820 0.5048 11.00000 0.05 0.66 Q17 1 0.2957 0.5636 0.7410 11.00000 0.05 0.65 Q18 1 0.7034 0.6850 0.2614 11.00000 0.05 0.65 Q19 1 0.2413 0.3195 0.2014 11.00000 0.05 0.57 Q20 1 0.7056 0.5580 0.7589 11.00000 0.05 0.52 ; _shelx_res_checksum 20981 _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 2.361 _oxdiff_exptl_absorpt_empirical_full_min 0.463 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I001 I 0.90138(4) 0.56618(2) 0.42046(3) 0.02740(13) Uani 1 1 d . . . . . I002 I 0.10057(4) 0.68812(2) 0.58028(3) 0.02725(13) Uani 1 1 d . . . . . F003 F -0.0670(8) 0.6851(3) 0.2898(4) 0.0433(17) Uani 1 1 d . . . . . O004 O 0.5421(7) 0.6936(2) 0.5394(4) 0.0259(13) Uani 1 1 d . . . . . F005 F 0.1031(7) 0.6193(2) 0.2909(3) 0.0450(13) Uani 1 1 d . . . . . O006 O 0.4613(7) 0.5581(2) 0.4599(4) 0.0248(12) Uani 1 1 d . . . . . O007 O 0.4058(7) 0.5851(2) 0.6577(3) 0.0330(13) Uani 1 1 d . . . . . F008 F 0.9005(7) 0.6242(3) 0.7107(3) 0.0490(14) Uani 1 1 d . . . . . O009 O 0.7706(6) 0.7185(3) 0.5474(4) 0.0381(15) Uani 1 1 d . . . . . F00A F 0.9237(11) 0.5514(4) 0.7877(3) 0.067(2) Uani 1 1 d . . . . . F00B F 0.0765(10) 0.6922(3) 0.2114(4) 0.0541(19) Uani 1 1 d . . . . . O00C O 0.5961(7) 0.6676(3) 0.3424(3) 0.0326(13) Uani 1 1 d . . . . . O00D O 0.5495(9) 0.5722(3) 0.3067(4) 0.0428(18) Uani 1 1 d . . . . . O00E O 0.4530(9) 0.6804(3) 0.6924(4) 0.0458(19) Uani 1 1 d . . . . . C00F C 0.6932(12) 0.4374(4) 0.6279(6) 0.0313(19) Uani 1 1 d . . . . . H00F H 0.668577 0.398716 0.640471 0.038 Uiso 1 1 calc R . . . . O00G O 0.2308(7) 0.5302(3) 0.4521(4) 0.0351(13) Uani 1 1 d . . . . . C00H C 0.0724(12) 0.6789(4) 0.2822(6) 0.034(2) Uani 1 1 d . . . . . F00I F 1.0705(9) 0.5597(3) 0.7098(6) 0.067(3) Uani 1 1 d . . . . . C00J C 0.5273(16) 0.6864(4) 0.2679(7) 0.042(3) Uani 1 1 d . . . . . H00A H 0.596202 0.682210 0.235246 0.063 Uiso 1 1 calc GR . . . . H00B H 0.497551 0.727680 0.268875 0.063 Uiso 1 1 calc GR . . . . H00C H 0.442547 0.661747 0.249939 0.063 Uiso 1 1 calc GR . . . . C00K C 0.5282(9) 0.4243(3) 0.5024(5) 0.0244(15) Uani 1 1 d . . . . . C00L C 0.6327(9) 0.4603(3) 0.5563(4) 0.0235(15) Uani 1 1 d . . . . . C00M C 0.4012(8) 0.4498(3) 0.4560(4) 0.0228(14) Uani 1 1 d . . . . . C00N C 0.2299(8) 0.6950(3) 0.4081(5) 0.0234(15) Uani 1 1 d . . . . . H00N H 0.202557 0.657172 0.422272 0.028 Uiso 1 1 calc R . . . . C00O C 0.3910(8) 0.7120(3) 0.5377(4) 0.0208(13) Uani 1 1 d . . . . . H00O H 0.391930 0.746811 0.570689 0.025 Uiso 1 1 calc R . . . . C00P C 0.6774(8) 0.5172(3) 0.5380(4) 0.0232(14) Uani 1 1 d . . . . . C00Q C 0.3246(8) 0.7308(3) 0.4590(4) 0.0217(14) Uani 1 1 d . . . . . C00R C 0.3574(8) 0.5144(3) 0.4569(4) 0.0244(15) Uani 1 1 d . . . . . C00S C 0.6033(9) 0.8010(3) 0.5363(5) 0.0246(15) Uani 1 1 d . . . . . C00T C 0.4753(9) 0.8246(4) 0.4900(5) 0.0247(16) Uani 1 1 d . . . . . C00U C 0.3692(8) 0.7874(3) 0.4376(4) 0.0256(16) Uani 1 1 d . . . . . C00V C 0.6463(8) 0.7356(4) 0.5407(5) 0.0270(16) Uani 1 1 d . . . . . C00W C 0.3304(9) 0.3515(4) 0.4010(5) 0.0304(17) Uani 1 1 d . . . . . C00X C 0.3033(8) 0.4127(3) 0.4077(4) 0.0261(15) Uani 1 1 d . . . . . H00X H 0.218080 0.429390 0.379291 0.031 Uiso 1 1 calc R . . . . C00Y C 0.1765(9) 0.7161(4) 0.3363(5) 0.0302(17) Uani 1 1 d . . . . . C00Z C 0.7874(11) 0.4710(4) 0.6791(5) 0.0364(19) Uani 1 1 d . . . . . H00Z H 0.825419 0.455240 0.726197 0.044 Uiso 1 1 calc R . . . . C010 C 0.6014(8) 0.6082(3) 0.3523(4) 0.0253(15) Uani 1 1 d . . . . . C011 C 0.4007(9) 0.6439(3) 0.6469(4) 0.0254(15) Uani 1 1 d . . . . . C012 C 0.6123(8) 0.5396(3) 0.4603(4) 0.0222(14) Uani 1 1 d . . . . . H012 H 0.610137 0.506145 0.425127 0.027 Uiso 1 1 calc R . . . . C013 C 0.7722(9) 0.5517(3) 0.5903(5) 0.0265(15) Uani 1 1 d . . . . . H013 H 0.798858 0.590176 0.577886 0.032 Uiso 1 1 calc R . . . . C014 C 0.4548(9) 0.8868(3) 0.4921(5) 0.0307(17) Uani 1 1 d . . . . . H014 H 0.373547 0.903905 0.460787 0.037 Uiso 1 1 calc R . . . . C015 C 0.7030(8) 0.8399(3) 0.5805(4) 0.0249(15) Uani 1 1 d . . . . . H015 H 0.790020 0.824109 0.608204 0.030 Uiso 1 1 calc R . . . . C016 C 0.5496(9) 0.3625(3) 0.4961(5) 0.0293(16) Uani 1 1 d . . . . . H016 H 0.630714 0.344600 0.526527 0.035 Uiso 1 1 calc R . . . . C017 C 0.6768(9) 0.9012(3) 0.5846(5) 0.0280(16) Uani 1 1 d . . . . . C018 C 0.4543(11) 0.3273(4) 0.4463(6) 0.0343(19) Uani 1 1 d . . . . . H018 H 0.473752 0.286417 0.443027 0.041 Uiso 1 1 calc R . . . . C019 C 0.2175(9) 0.7732(4) 0.3150(5) 0.0316(17) Uani 1 1 d . . . . . H019 H 0.178904 0.787662 0.267334 0.038 Uiso 1 1 calc R . . . . C01A C 0.6841(8) 0.5935(3) 0.4307(4) 0.0218(14) Uani 1 1 d . . . . . H01A H 0.687442 0.628211 0.463984 0.026 Uiso 1 1 calc R . . . . C01B C 0.7817(12) 0.9411(4) 0.6374(6) 0.036(2) Uani 1 1 d . . . . . H01E H 0.736951 0.952972 0.678267 0.054 Uiso 1 1 calc GR . . . . H01F H 0.803835 0.976296 0.611114 0.054 Uiso 1 1 calc GR . . . . H01G H 0.871070 0.919494 0.656286 0.054 Uiso 1 1 calc GR . . . . C01C C 0.3164(8) 0.6598(3) 0.5692(4) 0.0238(15) Uani 1 1 d . . . . . H01H H 0.309955 0.624847 0.536049 0.029 Uiso 1 1 calc R . . . . C01D C 0.8266(10) 0.5286(4) 0.6611(5) 0.0318(17) Uani 1 1 d . . . . . C01E C 0.4786(16) 0.5662(4) 0.7320(6) 0.041(3) Uani 1 1 d . . . . . H01I H 0.478977 0.523036 0.734585 0.061 Uiso 1 1 calc GR . . . . H01J H 0.426807 0.582165 0.768247 0.061 Uiso 1 1 calc GR . . . . H01K H 0.578135 0.580730 0.742227 0.061 Uiso 1 1 calc GR . . . . C01F C 0.2277(13) 0.3123(4) 0.3463(6) 0.041(2) Uani 1 1 d . . . . . H01B H 0.132856 0.311077 0.359873 0.061 Uiso 1 1 calc GR . . . . H01C H 0.267200 0.272297 0.347381 0.061 Uiso 1 1 calc GR . . . . H01D H 0.217889 0.328577 0.296820 0.061 Uiso 1 1 calc GR . . . . C01G C 0.5513(11) 0.9235(4) 0.5390(6) 0.0318(19) Uani 1 1 d . . . . . H01L H 0.531353 0.964481 0.540049 0.038 Uiso 1 1 calc R . . . . C01H C 0.3151(10) 0.8081(4) 0.3646(6) 0.0311(19) Uani 1 1 d . . . . . H01M H 0.344879 0.845269 0.349579 0.037 Uiso 1 1 calc R . . . . C01I C 0.9314(14) 0.5648(4) 0.7171(6) 0.038(3) 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 I001 0.0249(2) 0.0253(2) 0.0331(3) -0.0006(2) 0.00833(19) -0.00178(19) I002 0.0235(2) 0.0246(2) 0.0344(3) 0.00133(19) 0.00754(18) -0.00109(18) F003 0.033(4) 0.048(4) 0.045(4) -0.007(2) -0.001(3) -0.007(2) O004 0.023(3) 0.016(3) 0.038(3) 0.002(2) 0.002(2) 0.004(2) F005 0.053(4) 0.032(3) 0.047(3) -0.005(2) 0.003(3) 0.001(2) O006 0.018(3) 0.013(2) 0.046(4) 0.000(2) 0.011(3) 0.0006(19) O007 0.045(4) 0.015(3) 0.036(3) 0.006(2) -0.002(3) 0.000(2) F008 0.064(4) 0.034(3) 0.047(3) -0.012(2) 0.005(3) -0.015(3) O009 0.023(3) 0.023(3) 0.068(4) -0.001(3) 0.007(3) 0.003(2) F00A 0.109(7) 0.062(4) 0.024(3) 0.003(3) 0.000(4) -0.038(4) F00B 0.085(5) 0.049(4) 0.027(3) -0.003(2) 0.009(3) -0.018(3) O00C 0.046(4) 0.016(3) 0.032(3) 0.000(2) -0.002(3) -0.002(2) O00D 0.065(5) 0.021(3) 0.035(4) -0.004(2) -0.010(3) -0.001(3) O00E 0.063(5) 0.024(3) 0.039(4) 0.004(2) -0.017(3) -0.005(3) C00F 0.042(5) 0.022(4) 0.029(4) 0.006(3) 0.006(4) -0.004(3) O00G 0.024(3) 0.022(3) 0.060(4) 0.003(3) 0.009(3) 0.005(2) C00H 0.040(6) 0.033(5) 0.028(5) -0.004(3) 0.001(4) -0.001(4) F00I 0.036(4) 0.071(5) 0.086(6) -0.018(4) -0.009(4) -0.006(3) C00J 0.051(7) 0.026(5) 0.045(7) 0.004(4) -0.001(5) 0.004(4) C00K 0.023(4) 0.019(3) 0.031(4) 0.002(3) 0.004(3) -0.001(3) C00L 0.026(4) 0.019(3) 0.028(4) 0.006(3) 0.009(3) -0.002(3) C00M 0.019(3) 0.017(3) 0.032(4) 0.004(3) 0.004(3) -0.001(3) C00N 0.025(4) 0.020(3) 0.027(4) 0.000(3) 0.008(3) -0.003(3) C00O 0.021(3) 0.012(3) 0.029(4) 0.001(3) 0.005(3) 0.000(3) C00P 0.025(4) 0.020(3) 0.025(3) 0.000(3) 0.006(3) -0.002(3) C00Q 0.021(3) 0.019(3) 0.025(3) 0.001(3) 0.005(3) -0.002(3) C00R 0.025(4) 0.016(3) 0.033(4) 0.004(3) 0.006(3) 0.002(3) C00S 0.026(4) 0.017(3) 0.032(4) 0.004(3) 0.007(3) 0.000(3) C00T 0.019(3) 0.020(4) 0.035(4) 0.004(3) 0.005(3) -0.001(3) C00U 0.019(4) 0.023(4) 0.034(4) 0.001(3) 0.001(3) 0.002(3) C00V 0.022(3) 0.024(4) 0.034(4) -0.004(3) 0.003(3) 0.003(3) C00W 0.030(4) 0.026(4) 0.036(4) 0.000(3) 0.008(3) -0.001(3) C00X 0.024(3) 0.021(3) 0.031(4) 0.003(3) 0.002(3) 0.001(3) C00Y 0.027(4) 0.035(4) 0.029(4) 0.000(3) 0.007(3) 0.006(3) C00Z 0.041(5) 0.039(5) 0.029(4) 0.006(4) 0.007(4) -0.002(4) C010 0.028(4) 0.019(3) 0.027(4) 0.001(3) 0.000(3) -0.001(3) C011 0.027(4) 0.017(3) 0.031(4) 0.000(3) 0.004(3) -0.003(3) C012 0.018(3) 0.017(3) 0.032(4) 0.002(3) 0.005(3) 0.003(3) C013 0.028(4) 0.020(3) 0.033(4) -0.002(3) 0.009(3) -0.005(3) C014 0.028(4) 0.020(4) 0.044(5) 0.010(3) 0.006(3) 0.001(3) C015 0.026(4) 0.018(3) 0.031(4) 0.004(3) 0.006(3) -0.001(3) C016 0.028(4) 0.018(3) 0.040(4) 0.001(3) 0.001(3) 0.002(3) C017 0.032(4) 0.019(4) 0.035(4) 0.001(3) 0.012(3) -0.005(3) C018 0.040(5) 0.019(4) 0.045(5) 0.007(3) 0.013(4) 0.005(3) C019 0.027(4) 0.035(4) 0.031(4) 0.006(3) 0.001(3) 0.002(3) C01A 0.023(3) 0.016(3) 0.027(4) -0.002(3) 0.006(3) -0.003(3) C01B 0.042(6) 0.022(4) 0.041(5) -0.002(3) 0.003(4) -0.009(3) C01C 0.022(3) 0.019(4) 0.031(4) 0.001(3) 0.006(3) -0.002(3) C01D 0.032(4) 0.036(5) 0.028(4) -0.004(3) 0.007(3) -0.006(3) C01E 0.059(8) 0.028(5) 0.031(6) 0.009(3) -0.001(5) 0.000(4) C01F 0.038(6) 0.040(6) 0.041(6) -0.005(4) 0.002(4) -0.006(4) C01G 0.038(5) 0.015(3) 0.044(5) 0.001(3) 0.012(4) -0.002(3) C01H 0.030(5) 0.023(4) 0.039(5) 0.009(3) 0.002(4) 0.000(3) C01I 0.043(6) 0.044(6) 0.027(5) -0.003(3) 0.004(4) -0.015(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables 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' I I -0.4742 1.8119 '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' 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 C00V O004 C00O 119.4(6) . . ? C00R O006 C012 118.0(6) . . ? C011 O007 C01E 115.1(6) . . ? C010 O00C C00J 114.3(6) . . ? C00Z C00F C00L 121.2(8) . . ? F003 C00H F005 105.8(8) . . ? F003 C00H F00B 107.0(9) . . ? F003 C00H C00Y 112.9(8) . . ? F005 C00H C00Y 111.9(8) . . ? F00B C00H F005 106.4(8) . . ? F00B C00H C00Y 112.4(9) . . ? C00M C00K C00L 122.5(7) . . ? C016 C00K C00L 120.3(7) . . ? C016 C00K C00M 117.2(7) . . ? C00F C00L C00K 120.7(7) . . ? C00P C00L C00F 118.0(7) . . ? C00P C00L C00K 121.3(7) . . ? C00K C00M C00R 124.8(7) . . ? C00X C00M C00K 119.8(7) . . ? C00X C00M C00R 115.4(7) . . ? C00Y C00N C00Q 119.7(7) . . ? O004 C00O C00Q 108.0(6) . . ? O004 C00O C01C 106.6(6) . . ? C00Q C00O C01C 116.3(6) . . ? C00L C00P C012 116.3(6) . . ? C00L C00P C013 120.9(7) . . ? C013 C00P C012 122.7(7) . . ? C00N C00Q C00O 124.1(7) . . ? C00N C00Q C00U 120.5(7) . . ? C00U C00Q C00O 115.4(6) . . ? O006 C00R C00M 119.7(6) . . ? O00G C00R O006 117.6(7) . . ? O00G C00R C00M 122.7(7) . . ? C00T C00S C00V 125.0(7) . . ? C015 C00S C00T 119.6(7) . . ? C015 C00S C00V 115.4(7) . . ? C00S C00T C00U 123.2(7) . . ? C014 C00T C00S 117.1(8) . . ? C014 C00T C00U 119.6(7) . . ? C00Q C00U C00T 121.0(7) . . ? C00Q C00U C01H 119.3(7) . . ? C01H C00U C00T 119.7(7) . . ? O004 C00V C00S 119.4(7) . . ? O009 C00V O004 117.1(7) . . ? O009 C00V C00S 123.5(7) . . ? C00X C00W C01F 121.3(8) . . ? C018 C00W C00X 118.1(8) . . ? C018 C00W C01F 120.6(8) . . ? C00W C00X C00M 121.6(7) . . ? C00N C00Y C00H 120.1(8) . . ? C00N C00Y C019 120.1(8) . . ? C019 C00Y C00H 119.7(8) . . ? C00F C00Z C01D 120.3(8) . . ? O00C C010 C01A 109.8(6) . . ? O00D C010 O00C 125.2(7) . . ? O00D C010 C01A 124.9(7) . . ? O007 C011 C01C 111.6(6) . . ? O00E C011 O007 124.8(7) . . ? O00E C011 C01C 123.6(7) . . ? O006 C012 C00P 107.6(6) . . ? O006 C012 C01A 105.2(6) . . ? C00P C012 C01A 118.2(6) . . ? C01D C013 C00P 119.7(7) . . ? C01G C014 C00T 121.9(8) . . ? C017 C015 C00S 122.4(7) . . ? C018 C016 C00K 122.0(8) . . ? C015 C017 C01B 120.8(8) . . ? C01G C017 C015 117.1(7) . . ? C01G C017 C01B 122.1(7) . . ? C016 C018 C00W 121.3(8) . . ? C01H C019 C00Y 120.3(8) . . ? C010 C01A I001 106.6(5) . . ? C010 C01A C012 109.4(6) . . ? C012 C01A I001 107.0(5) . . ? C00O C01C I002 108.3(5) . . ? C011 C01C I002 107.2(5) . . ? C011 C01C C00O 110.1(6) . . ? C00Z C01D C013 119.9(8) . . ? C00Z C01D C01I 119.9(8) . . ? C013 C01D C01I 120.1(8) . . ? C014 C01G C017 121.8(8) . . ? C019 C01H C00U 120.0(8) . . ? F008 C01I C01D 111.6(9) . . ? F00A C01I F008 104.5(9) . . ? F00A C01I C01D 112.7(8) . . ? F00I C01I F008 105.6(8) . . ? F00I C01I F00A 108.5(10) . . ? F00I C01I C01D 113.3(9) . . ? 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 I001 C01A 2.146(8) . ? I002 C01C 2.144(8) . ? F003 C00H 1.334(13) . ? O004 C00O 1.453(9) . ? O004 C00V 1.340(10) . ? F005 C00H 1.358(11) . ? O006 C00R 1.361(9) . ? O006 C012 1.456(9) . ? O007 C011 1.321(9) . ? O007 C01E 1.450(12) . ? F008 C01I 1.352(11) . ? O009 C00V 1.196(10) . ? F00A C01I 1.338(13) . ? F00B C00H 1.334(12) . ? O00C C00J 1.445(12) . ? O00C C010 1.331(9) . ? O00D C010 1.186(10) . ? O00E C011 1.194(10) . ? C00F C00L 1.409(12) . ? C00F C00Z 1.367(14) . ? O00G C00R 1.211(9) . ? C00H C00Y 1.485(13) . ? F00I C01I 1.327(15) . ? C00K C00L 1.472(11) . ? C00K C00M 1.422(10) . ? C00K C016 1.396(10) . ? C00L C00P 1.392(10) . ? C00M C00R 1.494(10) . ? C00M C00X 1.400(10) . ? C00N C00Q 1.393(11) . ? C00N C00Y 1.387(12) . ? C00O C00Q 1.504(10) . ? C00O C01C 1.521(10) . ? C00P C012 1.510(10) . ? C00P C013 1.393(11) . ? C00Q C00U 1.403(11) . ? C00S C00T 1.413(11) . ? C00S C00V 1.504(10) . ? C00S C015 1.399(11) . ? C00T C00U 1.481(11) . ? C00T C014 1.397(11) . ? C00U C01H 1.404(12) . ? C00W C00X 1.395(11) . ? C00W C018 1.383(13) . ? C00W C01F 1.511(13) . ? C00Y C019 1.402(13) . ? C00Z C01D 1.387(13) . ? C010 C01A 1.517(10) . ? C011 C01C 1.517(11) . ? C012 C01A 1.521(10) . ? C013 C01D 1.389(12) . ? C014 C01G 1.376(13) . ? C015 C017 1.391(11) . ? C016 C018 1.379(13) . ? C017 C01B 1.512(12) . ? C017 C01G 1.380(13) . ? C019 C01H 1.382(13) . ? C01D C01I 1.497(13) . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.91(3) 2 0.09(3)