#------------------------------------------------------------------------------ #$Date: 2020-07-06 05:03:52 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253819 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126466.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_7126466 loop_ _publ_author_name 'Tang, Pan-Ting' 'Shao, You-Xiang' 'Wang, Liang-Neng' '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_issue 49 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 6680 _journal_page_last 6683 _journal_paper_doi 10.1039/c9cc10080f _journal_volume 56 _journal_year 2020 _chemical_absolute_configuration S _chemical_formula_moiety 'C18 H14 F I O4' _chemical_formula_sum 'C18 H14 F I O4' _chemical_formula_weight 440.19 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _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 ; 2019-12-30 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.7643(3) _cell_length_b 9.1745(3) _cell_length_c 20.1935(8) _cell_measurement_reflns_used 4665 _cell_measurement_temperature 100.02(10) _cell_measurement_theta_max 28.1280 _cell_measurement_theta_min 2.0070 _cell_volume 1623.72(10) _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 100.02(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.832 _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 59.00 0.50 0.97 -- -9.20 57.00 -30.00 166 2 \w -16.00 10.00 0.50 0.97 -- -9.20 -37.00 24.00 52 3 \w -25.00 5.00 0.50 0.97 -- -9.20 -99.00 -60.00 60 4 \w -85.00 -29.00 0.50 0.97 -- -9.20 -37.00 24.00 112 5 \w 1.00 26.00 0.50 0.97 -- -9.20 57.00 150.00 50 ; _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 0.0683832000 _diffrn_orient_matrix_UB_12 0.0079174000 _diffrn_orient_matrix_UB_13 0.0184605000 _diffrn_orient_matrix_UB_21 0.0412122000 _diffrn_orient_matrix_UB_22 -0.0352736000 _diffrn_orient_matrix_UB_23 -0.0256252000 _diffrn_orient_matrix_UB_31 0.0133403000 _diffrn_orient_matrix_UB_32 0.0683318000 _diffrn_orient_matrix_UB_33 -0.0153618000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_unetI/netI 0.0590 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.832 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 9747 _diffrn_reflns_point_group_measured_fraction_full 0.963 _diffrn_reflns_point_group_measured_fraction_max 0.770 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.378 _diffrn_reflns_theta_min 2.017 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 2.002 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.38399 _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 1.801 _exptl_crystal_description block _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.508 _refine_diff_density_min -0.635 _refine_diff_density_rms 0.103 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.50(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 3767 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0333 _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^)+(0.0157P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.0597 _reflns_Friedel_coverage 0.626 _reflns_Friedel_fraction_full 0.915 _reflns_Friedel_fraction_max 0.688 _reflns_number_gt 3468 _reflns_number_total 3767 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc10080f2.cif _cod_data_source_block tpt-14-8 _cod_depositor_comments 'Adding full bibliography for 7126465--7126470.cif.' _cod_database_code 7126466 _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 0.690 _shelx_estimated_absorpt_t_min 0.690 _reflns_odcompleteness_completeness 99.64 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.50(3) 0.50(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: C4(H4), C3(H3) 3.b Aromatic/amide H refined with riding coordinates: C18(H18), C6(H6), C8(H8), C9(H9), C17(H17), C14(H14) 3.c Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL tpt-14-8_a.res in P2(1)2(1)2(1) tpt-14-8.res created by SHELXL-2018/3 at 18:11:16 on 14-Jun-2019 REM Old TITL tpt-14-8 in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1): R1 0.070, Rweak 0.028, Alpha 0.036 REM 0.624 for 23 systematic absences, Orientation as input REM Flack x = 0.021 ( 0.136 ) from 1134 Parsons' quotients REM Formula found by SHELXT: C17 N F1 I CELL 0.71073 8.7643 9.1745 20.1935 90 90 90 ZERR 4 0.0003 0.0003 0.0008 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H F I O UNIT 72 56 4 4 16 L.S. 4 0 0 PLAN 50 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 REM REM REM WGHT 0.015700 BASF 0.50479 FVAR 0.38583 I1 4 0.513286 0.912446 0.528649 11.00000 0.02310 0.01721 = 0.02821 0.00421 -0.00175 0.00026 O1 5 0.380236 0.641596 0.411444 11.00000 0.02235 0.04774 = 0.01611 -0.00838 -0.00219 -0.00326 O3 5 0.541671 0.444974 0.549280 11.00000 0.02455 0.01638 = 0.01833 0.00092 -0.00268 -0.00238 F1 3 0.230437 0.724022 0.749359 11.00000 0.03557 0.03706 = 0.02878 -0.00989 0.01024 0.00544 O4 5 0.610987 0.216720 0.557548 11.00000 0.03453 0.01688 = 0.03111 -0.00382 -0.00648 -0.00208 O2 5 0.632541 0.623722 0.425879 11.00000 0.02172 0.05432 = 0.02608 0.00272 0.00009 0.00845 C18 1 0.917588 0.510745 0.692216 11.00000 0.02878 0.01709 = 0.02227 -0.00162 -0.00686 -0.00412 AFIX 43 H18 2 0.920602 0.577159 0.726984 11.00000 -1.20000 AFIX 0 C2 1 0.506767 0.646330 0.446836 11.00000 0.01785 0.01928 = 0.02294 0.00496 -0.00272 -0.00098 C4 1 0.569928 0.598686 0.565970 11.00000 0.02375 0.01033 = 0.01963 0.00005 -0.00088 -0.00125 AFIX 13 H4 2 0.677308 0.623056 0.558183 11.00000 -1.20000 AFIX 0 C12 1 0.640386 0.341884 0.571016 11.00000 0.02671 0.01700 = 0.01284 0.00068 0.00068 -0.00047 C6 1 0.396115 0.672380 0.661113 11.00000 0.02791 0.01578 = 0.02295 -0.00260 0.00046 0.00031 AFIX 43 H6 2 0.325430 0.710758 0.631518 11.00000 -1.20000 AFIX 0 C11 1 0.780804 0.486833 0.659848 11.00000 0.02732 0.01174 = 0.01604 0.00389 0.00082 -0.00164 C0AA 1 0.531932 0.615408 0.638770 11.00000 0.02856 0.01078 = 0.01766 0.00076 -0.00018 -0.00242 C3 1 0.468793 0.682487 0.518328 11.00000 0.01800 0.01809 = 0.01904 0.00242 -0.00242 -0.00012 AFIX 13 H3 2 0.361100 0.661764 0.527378 11.00000 -1.20000 AFIX 0 C10 1 0.637995 0.557125 0.682975 11.00000 0.03138 0.01422 = 0.01713 -0.00250 -0.00503 -0.00098 C15 1 1.050300 0.335918 0.624061 11.00000 0.02820 0.02285 = 0.02313 0.01001 0.00127 0.00002 C13 1 0.780116 0.384812 0.607773 11.00000 0.02342 0.01304 = 0.01701 0.00402 -0.00179 -0.00211 C8 1 0.468650 0.619242 0.773914 11.00000 0.04612 0.02066 = 0.01561 -0.00460 0.00120 -0.00114 AFIX 43 H8 2 0.446865 0.622322 0.818965 11.00000 -1.20000 AFIX 0 C9 1 0.605531 0.561440 0.751414 11.00000 0.04118 0.01692 = 0.01887 -0.00545 -0.00512 -0.00073 AFIX 43 H9 2 0.676231 0.525362 0.781593 11.00000 -1.20000 AFIX 0 C16 1 1.196645 0.259882 0.603716 11.00000 0.02356 0.05011 = 0.02993 0.00183 -0.00255 0.00967 AFIX 137 H16A 2 1.242510 0.311564 0.567488 11.00000 -1.50000 H16B 2 1.174088 0.161859 0.590267 11.00000 -1.50000 H16C 2 1.265965 0.258096 0.640516 11.00000 -1.50000 AFIX 0 C7 1 0.366570 0.671498 0.728675 11.00000 0.03215 0.01612 = 0.02678 -0.01036 0.00694 -0.00097 C17 1 1.049820 0.438898 0.674422 11.00000 0.02559 0.02931 = 0.02258 0.00398 -0.00777 -0.00460 AFIX 43 H17 2 1.140208 0.459886 0.696583 11.00000 -1.20000 AFIX 0 C14 1 0.912511 0.309109 0.592297 11.00000 0.03163 0.01399 = 0.02097 0.00400 0.00002 0.00286 AFIX 43 H14 2 0.908862 0.237969 0.559527 11.00000 -1.20000 AFIX 0 C1 1 0.397002 0.602163 0.341973 11.00000 0.04521 0.04712 = 0.01560 -0.00732 -0.00465 -0.00467 AFIX 137 H1A 2 0.304283 0.624204 0.318726 11.00000 -1.50000 H1B 2 0.418114 0.499775 0.338480 11.00000 -1.50000 H1C 2 0.479661 0.656513 0.322914 11.00000 -1.50000 AFIX 0 HKLF 4 REM tpt-14-8_a.res in P2(1)2(1)2(1) REM wR2 = 0.0597, GooF = S = 1.021, Restrained GooF = 1.021 for all data REM R1 = 0.0333 for 3468 Fo > 4sig(Fo) and 0.0396 for all 3767 data REM 220 parameters refined using 0 restraints END WGHT 0.0157 0.0000 REM Highest difference peak 0.508, deepest hole -0.635, 1-sigma level 0.103 Q1 1 0.5233 0.6359 0.5406 11.00000 0.05 0.51 Q2 1 0.5147 0.8945 0.4944 11.00000 0.05 0.51 Q3 1 0.4793 0.6416 0.4775 11.00000 0.05 0.46 Q4 1 0.4788 1.0009 0.4977 11.00000 0.05 0.40 Q5 1 0.5080 0.5332 0.7624 11.00000 0.05 0.40 Q6 1 0.5953 0.9145 0.5846 11.00000 0.05 0.39 Q7 1 1.0101 0.2362 0.5816 11.00000 0.05 0.38 Q8 1 0.4618 0.9186 0.5858 11.00000 0.05 0.38 Q9 1 0.9183 0.4768 0.7204 11.00000 0.05 0.37 Q10 1 1.3173 0.4172 0.6194 11.00000 0.05 0.37 Q11 1 0.5059 0.8927 0.5602 11.00000 0.05 0.37 Q12 1 1.4029 0.3653 0.5805 11.00000 0.05 0.35 Q13 1 0.4788 0.4597 0.6160 11.00000 0.05 0.35 Q14 1 0.9855 0.2842 0.6999 11.00000 0.05 0.35 Q15 1 0.4903 0.0943 0.5791 11.00000 0.05 0.34 Q16 1 0.4716 0.7857 0.4812 11.00000 0.05 0.34 Q17 1 0.8316 0.4211 0.6265 11.00000 0.05 0.34 Q18 1 0.2731 0.6665 0.4782 11.00000 0.05 0.34 Q19 1 0.7462 0.6552 0.4799 11.00000 0.05 0.33 Q20 1 0.5183 0.9060 0.4196 11.00000 0.05 0.33 Q21 1 0.1346 0.5951 0.6004 11.00000 0.05 0.32 Q22 1 0.5015 0.7369 0.5598 11.00000 0.05 0.32 Q23 1 0.6190 0.9452 0.4782 11.00000 0.05 0.32 Q24 1 0.3383 0.6380 0.3813 11.00000 0.05 0.32 Q25 1 0.9710 0.1048 0.5206 11.00000 0.05 0.32 Q26 1 0.5395 0.5847 0.8233 11.00000 0.05 0.32 Q27 1 0.2823 0.6762 0.5981 11.00000 0.05 0.32 Q28 1 0.8643 0.6010 0.6412 11.00000 0.05 0.31 Q29 1 0.4145 0.9204 0.4765 11.00000 0.05 0.31 Q30 1 0.5074 0.2614 0.5270 11.00000 0.05 0.31 Q31 1 0.9653 0.4046 0.6212 11.00000 0.05 0.31 Q32 1 1.3305 0.4152 0.6844 11.00000 0.05 0.31 Q33 1 0.7539 0.6421 0.6792 11.00000 0.05 0.30 Q34 1 0.8090 0.3132 0.6202 11.00000 0.05 0.30 Q35 1 0.5412 0.5440 0.5552 11.00000 0.05 0.30 Q36 1 0.6376 0.6408 0.7011 11.00000 0.05 0.30 Q37 1 0.3631 0.8074 0.4986 11.00000 0.05 0.30 Q38 1 0.4875 0.1646 0.5008 11.00000 0.05 0.30 Q39 1 0.2413 0.6805 0.8199 11.00000 0.05 0.30 Q40 1 0.5228 0.6670 0.6411 11.00000 0.05 0.29 Q41 1 0.4331 0.4193 0.2961 11.00000 0.05 0.29 Q42 1 0.8079 0.5761 0.5932 11.00000 0.05 0.29 Q43 1 0.3958 0.4735 0.5809 11.00000 0.05 0.29 Q44 1 0.3622 0.7224 0.7371 11.00000 0.05 0.29 Q45 1 0.5389 0.4552 0.5795 11.00000 0.05 0.29 Q46 1 0.4006 0.8812 0.5267 11.00000 0.05 0.29 Q47 1 0.5168 0.4667 0.3561 11.00000 0.05 0.29 Q48 1 0.4812 0.6360 0.2994 11.00000 0.05 0.29 Q49 1 0.4754 0.8121 0.5122 11.00000 0.05 0.28 Q50 1 0.5211 0.5656 0.5985 11.00000 0.05 0.28 ; _shelx_res_checksum 83504 _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 1.658 _oxdiff_exptl_absorpt_empirical_full_min 0.488 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.51329(3) 0.91245(3) 0.52865(2) 0.02284(9) Uani 1 1 d . . . . . O1 O 0.3802(5) 0.6416(4) 0.41144(18) 0.0287(10) Uani 1 1 d . . . . . O3 O 0.5417(4) 0.4450(3) 0.54928(14) 0.0198(7) Uani 1 1 d . . . . . F1 F 0.2304(4) 0.7240(3) 0.74936(13) 0.0338(7) Uani 1 1 d . . . . . O4 O 0.6110(5) 0.2167(3) 0.55755(17) 0.0275(9) Uani 1 1 d . . . . . O2 O 0.6325(4) 0.6237(4) 0.42588(18) 0.0340(10) Uani 1 1 d . . . . . C18 C 0.9176(6) 0.5107(5) 0.6922(2) 0.0227(11) Uani 1 1 d . . . . . H18 H 0.920602 0.577159 0.726984 0.027 Uiso 1 1 calc R . . . . C2 C 0.5068(7) 0.6463(4) 0.4468(2) 0.0200(10) Uani 1 1 d . . . . . C4 C 0.5699(6) 0.5987(5) 0.5660(2) 0.0179(10) Uani 1 1 d . . . . . H4 H 0.677308 0.623056 0.558183 0.021 Uiso 1 1 calc R . . . . C12 C 0.6404(6) 0.3419(5) 0.5710(2) 0.0188(10) Uani 1 1 d . . . . . C6 C 0.3961(6) 0.6724(5) 0.6611(2) 0.0222(11) Uani 1 1 d . . . . . H6 H 0.325430 0.710758 0.631518 0.027 Uiso 1 1 calc R . . . . C11 C 0.7808(6) 0.4868(5) 0.6598(2) 0.0184(10) Uani 1 1 d . . . . . C0AA C 0.5319(6) 0.6154(4) 0.6388(2) 0.0190(11) Uani 1 1 d . . . . . C3 C 0.4688(6) 0.6825(4) 0.5183(2) 0.0184(10) Uani 1 1 d . . . . . H3 H 0.361100 0.661764 0.527378 0.022 Uiso 1 1 calc R . . . . C10 C 0.6380(6) 0.5571(5) 0.6830(2) 0.0209(11) Uani 1 1 d . . . . . C15 C 1.0503(6) 0.3359(5) 0.6241(2) 0.0247(12) Uani 1 1 d . . . . . C13 C 0.7801(6) 0.3848(5) 0.6078(2) 0.0178(10) Uani 1 1 d . . . . . C8 C 0.4687(7) 0.6192(5) 0.7739(2) 0.0275(13) Uani 1 1 d . . . . . H8 H 0.446865 0.622322 0.818965 0.033 Uiso 1 1 calc R . . . . C9 C 0.6055(6) 0.5614(5) 0.7514(2) 0.0257(12) Uani 1 1 d . . . . . H9 H 0.676231 0.525362 0.781593 0.031 Uiso 1 1 calc R . . . . C16 C 1.1966(6) 0.2599(6) 0.6037(3) 0.0345(13) Uani 1 1 d . . . . . H16A H 1.242510 0.311564 0.567488 0.052 Uiso 1 1 calc GR . . . . H16B H 1.174088 0.161859 0.590267 0.052 Uiso 1 1 calc GR . . . . H16C H 1.265965 0.258096 0.640516 0.052 Uiso 1 1 calc GR . . . . C7 C 0.3666(7) 0.6715(5) 0.7287(3) 0.0250(12) Uani 1 1 d . . . . . C17 C 1.0498(6) 0.4389(5) 0.6744(2) 0.0258(12) Uani 1 1 d . . . . . H17 H 1.140208 0.459886 0.696583 0.031 Uiso 1 1 calc R . . . . C14 C 0.9125(7) 0.3091(5) 0.5923(3) 0.0222(12) Uani 1 1 d . . . . . H14 H 0.908862 0.237969 0.559527 0.027 Uiso 1 1 calc R . . . . C1 C 0.3970(7) 0.6022(6) 0.3420(2) 0.0360(14) Uani 1 1 d . . . . . H1A H 0.304283 0.624204 0.318726 0.054 Uiso 1 1 calc GR . . . . H1B H 0.418114 0.499775 0.338480 0.054 Uiso 1 1 calc GR . . . . H1C H 0.479661 0.656513 0.322914 0.054 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 I1 0.02310(16) 0.01721(15) 0.02821(15) 0.00421(12) -0.00175(15) 0.00026(13) O1 0.022(2) 0.048(2) 0.0161(18) -0.0084(16) -0.0022(17) -0.0033(16) O3 0.025(2) 0.0164(16) 0.0183(14) 0.0009(11) -0.0027(14) -0.0024(13) F1 0.036(2) 0.0371(18) 0.0288(16) -0.0099(14) 0.0102(14) 0.0054(14) O4 0.035(2) 0.0169(19) 0.0311(19) -0.0038(14) -0.0065(17) -0.0021(15) O2 0.022(2) 0.054(3) 0.026(2) 0.0027(18) 0.0001(17) 0.0085(17) C18 0.029(3) 0.017(2) 0.022(3) -0.002(2) -0.007(2) -0.004(2) C2 0.018(3) 0.019(2) 0.023(2) 0.0050(16) -0.003(2) -0.001(2) C4 0.024(3) 0.010(2) 0.020(2) 0.0001(18) -0.0009(19) -0.001(2) C12 0.027(3) 0.017(2) 0.013(2) 0.0007(18) 0.001(2) 0.000(2) C6 0.028(3) 0.016(2) 0.023(2) -0.003(2) 0.000(2) 0.000(2) C11 0.027(3) 0.012(2) 0.016(2) 0.0039(18) 0.001(2) -0.0016(19) C0AA 0.029(3) 0.011(2) 0.018(2) 0.0008(16) 0.000(2) -0.002(2) C3 0.018(3) 0.018(2) 0.019(2) 0.0024(16) -0.002(2) -0.0001(18) C10 0.031(3) 0.014(2) 0.017(2) -0.0025(18) -0.005(2) -0.0010(19) C15 0.028(3) 0.023(3) 0.023(2) 0.010(2) 0.001(2) 0.000(2) C13 0.023(3) 0.013(2) 0.017(2) 0.0040(18) -0.002(2) -0.0021(18) C8 0.046(4) 0.021(2) 0.016(2) -0.0046(17) 0.001(2) -0.001(2) C9 0.041(4) 0.017(3) 0.019(2) -0.005(2) -0.005(2) -0.001(2) C16 0.024(3) 0.050(4) 0.030(3) 0.002(3) -0.003(2) 0.010(3) C7 0.032(3) 0.016(2) 0.027(3) -0.010(2) 0.007(3) -0.001(2) C17 0.026(3) 0.029(3) 0.023(2) 0.004(2) -0.008(2) -0.005(2) C14 0.032(3) 0.014(2) 0.021(3) 0.004(2) 0.000(2) 0.003(2) C1 0.045(4) 0.047(3) 0.016(2) -0.007(3) -0.005(2) -0.005(3) 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 C2 O1 C1 116.4(4) . . ? C12 O3 C4 119.2(4) . . ? C17 C18 C11 121.9(4) . . ? O1 C2 C3 109.7(5) . . ? O2 C2 O1 125.1(4) . . ? O2 C2 C3 125.1(5) . . ? O3 C4 C0AA 106.4(3) . . ? O3 C4 C3 104.0(3) . . ? C0AA C4 C3 115.8(4) . . ? O3 C12 C13 120.2(4) . . ? O4 C12 O3 117.0(4) . . ? O4 C12 C13 122.7(4) . . ? C0AA C6 C7 118.8(5) . . ? C18 C11 C10 120.9(4) . . ? C18 C11 C13 117.5(4) . . ? C13 C11 C10 121.4(4) . . ? C6 C0AA C4 123.1(4) . . ? C6 C0AA C10 120.8(4) . . ? C10 C0AA C4 115.8(4) . . ? C2 C3 I1 105.4(3) . . ? C4 C3 I1 109.2(3) . . ? C4 C3 C2 111.4(4) . . ? C0AA C10 C11 121.8(4) . . ? C0AA C10 C9 118.8(5) . . ? C9 C10 C11 119.4(4) . . ? C17 C15 C16 120.9(5) . . ? C17 C15 C14 117.1(5) . . ? C14 C15 C16 121.9(4) . . ? C11 C13 C12 123.6(4) . . ? C14 C13 C12 116.4(4) . . ? C14 C13 C11 119.8(5) . . ? C7 C8 C9 118.8(4) . . ? C8 C9 C10 120.4(5) . . ? F1 C7 C6 117.8(5) . . ? F1 C7 C8 119.8(5) . . ? C8 C7 C6 122.5(5) . . ? C18 C17 C15 121.2(5) . . ? C13 C14 C15 122.3(4) . . ? 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 I1 C3 2.156(4) . ? O1 C2 1.320(6) . ? O1 C1 1.456(5) . ? O3 C4 1.471(5) . ? O3 C12 1.355(5) . ? F1 C7 1.353(6) . ? O4 C12 1.208(5) . ? O2 C2 1.199(6) . ? C18 C11 1.383(7) . ? C18 C17 1.381(7) . ? C2 C3 1.518(6) . ? C4 C0AA 1.515(6) . ? C4 C3 1.517(6) . ? C12 C13 1.485(7) . ? C6 C0AA 1.376(7) . ? C6 C7 1.389(7) . ? C11 C10 1.483(7) . ? C11 C13 1.408(6) . ? C0AA C10 1.395(7) . ? C10 C9 1.412(6) . ? C15 C16 1.517(7) . ? C15 C17 1.388(7) . ? C15 C14 1.389(7) . ? C13 C14 1.388(7) . ? C8 C9 1.388(8) . ? C8 C7 1.366(8) . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.50(3) 2 0.50(3)