#------------------------------------------------------------------------------ #$Date: 2020-07-06 05:00:53 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253814 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126494.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_7126494 loop_ _publ_author_name 'Cheng, Ruixiang' 'Xiong, Wenfang' 'Qi, Chaorong' 'Wang, Lu' 'Ren, Yanwei' 'Jiang, Huanfeng' _publ_section_title ; Macrocyclization of 3-triflyloxybenzynes with tetrahydrofuran via an anionic thia-Fries rearrangement. ; _journal_issue 48 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 6495 _journal_page_last 6498 _journal_paper_doi 10.1039/d0cc00135j _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C19 H23.27 F3 O6 S' _chemical_formula_sum 'C19 H24.04 F3 O6 S' _chemical_formula_weight 437.48 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2018-02-27 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2019-12-23 deposited with the CCDC. 2020-05-04 downloaded from the CCDC. ; _cell_angle_alpha 94.471(5) _cell_angle_beta 104.322(6) _cell_angle_gamma 108.484(6) _cell_formula_units_Z 2 _cell_length_a 9.3575(6) _cell_length_b 10.2713(6) _cell_length_c 11.5278(7) _cell_measurement_reflns_used 4707 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 28.1110 _cell_measurement_theta_min 2.5890 _cell_volume 1003.31(12) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _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 100.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 -88.00 21.00 1.00 5.00 -- -11.59 -77.00-150.00 109 2 \w -60.00 40.00 1.00 5.00 -- 11.74 -57.00 -30.00 100 3 \w -16.00 85.00 1.00 5.00 -- 11.74 57.00 120.00 101 4 \w 34.00 99.00 1.00 5.00 -- 11.74-178.00 -30.00 65 5 \w -13.00 28.00 1.00 5.00 -- 11.74 37.00 30.00 41 6 \w -20.00 53.00 1.00 5.00 -- 11.74 -99.00 150.00 73 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0765336000 _diffrn_orient_matrix_UB_12 -0.0187115000 _diffrn_orient_matrix_UB_13 0.0074777000 _diffrn_orient_matrix_UB_21 0.0256426000 _diffrn_orient_matrix_UB_22 -0.0268836000 _diffrn_orient_matrix_UB_23 0.0530161000 _diffrn_orient_matrix_UB_31 0.0212010000 _diffrn_orient_matrix_UB_32 0.0662341000 _diffrn_orient_matrix_UB_33 0.0358648000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_unetI/netI 0.0447 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 11219 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.998 _diffrn_reflns_theta_max 24.998 _diffrn_reflns_theta_min 2.122 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68769 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) 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 1.448 _exptl_crystal_description block _exptl_crystal_F_000 458 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _refine_diff_density_max 1.589 _refine_diff_density_min -1.564 _refine_diff_density_rms 0.150 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 3536 _refine_ls_number_restraints 27 _refine_ls_restrained_S_all 1.093 _refine_ls_R_factor_all 0.1417 _refine_ls_R_factor_gt 0.0668 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1776P)^2^+7.5871P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3224 _refine_ls_wR_factor_ref 0.3380 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2932 _reflns_number_total 3536 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL crx-440_a.res in P-1 crx-440.res created by SHELXL-2017/1 at 09:45:25 on 27-Feb-2018 REM Old TITL CRX-440 in P-1 #2 REM SHELXT solution in P-1 REM R1 0.251, Rweak 0.019, Alpha 0.065, Orientation as input REM Formula found by SHELXT: C19 N O3 S F6 CELL 0.71073 9.357479 10.271277 11.527788 94.4707 104.3218 108.4838 ZERR 2 0.000635 0.00061 0.000705 0.0049 0.0056 0.0057 LATT 1 SFAC C H F O S UNIT 38 48.08 6 12 2 DELU C14 O5 DELU S1 C19 DELU O5 C15 SIMU 0.005 0.01 2 C14 O5 SIMU 0.001 0.002 2 S1 C19 SIMU 0.002 0.004 2 O5 C15 ISOR C19 L.S. 20 PLAN 20 SIZE 0.12 0.13 0.14 BOND $H LIST 6 MORE -1 CONF fmap 2 53 acta 52 OMIT -3 50 REM REM REM WGHT 0.177600 7.587100 FVAR 0.68608 0.46139 S1 5 0.473413 0.237780 0.251480 11.00000 0.02717 0.02705 = 0.02475 0.00821 0.00577 0.01100 F3 3 0.446860 0.116325 0.036596 11.00000 0.04418 0.05493 = 0.02827 0.00569 0.01718 0.01827 F1 3 0.513608 0.007535 0.185071 11.00000 0.05328 0.02723 = 0.06230 0.01837 0.02894 0.01975 O6 4 0.308772 -0.008543 0.347866 11.00000 0.02402 0.03265 = 0.02328 0.01771 0.01281 0.01753 O3 4 0.226867 0.283071 0.060808 11.00000 0.01807 0.03470 = 0.02194 0.01685 0.00267 0.01095 O2 4 0.514387 0.371813 0.216404 11.00000 0.02351 0.02371 = 0.03374 0.01387 0.00769 0.01014 O1 4 0.554127 0.233684 0.372266 11.00000 0.02123 0.05420 = 0.02135 0.01663 0.00206 0.01759 F2 3 0.682832 0.192571 0.157863 11.00000 0.03906 0.05297 = 0.08108 0.01969 0.03354 0.02112 O4 4 0.161321 0.589186 0.182043 11.00000 0.04052 0.02890 = 0.03933 0.00637 -0.01500 0.01446 O5 4 0.150915 0.267701 0.595236 11.00000 0.07669 0.03332 = 0.02297 0.00686 0.00738 0.01829 C2 1 0.042193 -0.025914 0.249235 11.00000 0.02294 0.01884 = 0.02175 0.00470 0.01022 0.00403 AFIX 43 H2 2 0.000566 -0.096710 0.289953 11.00000 -1.20000 AFIX 0 C4 1 0.000977 0.125585 0.103976 11.00000 0.01833 0.03292 = 0.01290 0.00662 0.00178 0.00910 AFIX 43 H4 2 -0.068743 0.155333 0.049684 11.00000 -1.20000 AFIX 0 C3 1 -0.055243 0.020843 0.167023 11.00000 0.02002 0.02836 = 0.01744 -0.00008 0.00068 0.00282 AFIX 43 H3 2 -0.163391 -0.019451 0.153101 11.00000 -1.20000 AFIX 0 C5 1 0.163098 0.186562 0.122215 11.00000 0.01747 0.02976 = 0.01964 0.00795 0.00553 0.00929 C1 1 0.204828 0.034274 0.270963 11.00000 0.02403 0.02709 = 0.01921 0.00703 0.00849 0.01240 C17 1 0.221123 0.011744 0.530463 11.00000 0.02082 0.03243 = 0.01728 0.01262 0.00404 0.01089 AFIX 23 H17A 2 0.208305 -0.033669 0.599798 11.00000 -1.20000 H17B 2 0.121290 0.020450 0.490226 11.00000 -1.20000 AFIX 0 C18 1 0.261873 -0.079010 0.443396 11.00000 0.02405 0.03727 = 0.03600 0.02366 0.01576 0.01815 AFIX 23 H18A 2 0.346859 -0.106510 0.488194 11.00000 -1.20000 H18B 2 0.171242 -0.162904 0.407344 11.00000 -1.20000 AFIX 0 C6 1 0.266250 0.145749 0.211179 11.00000 0.01956 0.03724 = 0.02718 0.01618 0.01015 0.01435 C7 1 0.128346 0.349162 -0.011855 11.00000 0.02065 0.04246 = 0.02186 0.01875 0.00103 0.01518 AFIX 23 H7A 2 0.065127 0.376507 0.033715 11.00000 -1.20000 H7B 2 0.058589 0.285673 -0.085446 11.00000 -1.20000 AFIX 0 C16 1 0.344446 0.156150 0.575286 11.00000 0.02666 0.05464 = 0.02828 -0.00410 0.00814 -0.00809 AFIX 23 H16A 2 0.365741 0.197238 0.505647 11.00000 -1.20000 H16B 2 0.441153 0.147632 0.623045 11.00000 -1.20000 AFIX 0 C15 1 0.297503 0.254063 0.651986 11.00000 0.07128 0.03564 = 0.02177 0.00553 0.01119 0.01183 AFIX 23 H15A 2 0.292475 0.220455 0.727735 11.00000 -1.20000 H15B 2 0.378907 0.345459 0.671622 11.00000 -1.20000 AFIX 0 PART 1 C19 1 0.527884 0.129285 0.151499 11.00000 0.03129 0.02765 = 0.02617 0.00812 0.00429 0.00996 PART 0 C8 1 0.238812 0.475593 -0.042455 11.00000 0.03090 0.07251 = 0.06153 0.05478 0.02471 0.02855 AFIX 23 H8A 2 0.176613 0.519605 -0.094631 11.00000 -1.20000 H8B 2 0.299745 0.444943 -0.088329 11.00000 -1.20000 AFIX 0 C10 1 0.276192 0.666521 0.128400 11.00000 0.02808 0.02323 = 0.10201 0.03386 -0.01579 -0.00128 AFIX 23 H10A 2 0.358718 0.737861 0.191346 11.00000 -1.20000 H10B 2 0.227058 0.713449 0.069568 11.00000 -1.20000 AFIX 0 C9 1 0.351192 0.583226 0.065850 11.00000 0.01477 0.04491 = 0.10991 0.05453 0.00681 0.00845 AFIX 23 H9A 2 0.400869 0.536415 0.124472 11.00000 -1.20000 H9B 2 0.433217 0.647062 0.039318 11.00000 -1.20000 AFIX 0 C11 1 0.224648 0.550998 0.293975 11.00000 0.09778 0.02982 = 0.03923 -0.00812 -0.03557 0.03666 AFIX 23 H11A 2 0.284800 0.633703 0.354983 11.00000 -1.20000 H11B 2 0.294201 0.501008 0.283865 11.00000 -1.20000 AFIX 0 C12 1 0.092453 0.461061 0.333087 11.00000 0.17563 0.02583 = 0.02465 0.00288 -0.00830 0.02866 PART 2 AFIX 23 H12A 2 0.031372 0.375838 0.275231 -21.00000 -1.20000 H12B 2 0.023784 0.509573 0.348857 -21.00000 -1.20000 AFIX 0 PART 0 C14 1 0.135921 0.314785 0.481876 11.00000 0.12283 0.04646 = 0.03104 0.00793 0.00819 0.03672 PART 1 AFIX 43 H14 2 0.164912 0.273587 0.421054 21.00000 -1.20000 AFIX 43 PART 0 PART 2 H14A 2 0.069279 0.247869 0.414884 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C13 1 0.082325 0.414276 0.463273 21.00000 0.02966 0.02324 = 0.02670 0.00906 0.01055 0.01625 AFIX 43 H13 2 0.042800 0.454433 0.517264 0.07900 -1.20000 AFIX 0 PART 0 PART 2 C00V 1 0.199010 0.433103 0.458344 -21.00000 0.02390 0.03394 = 0.02499 0.00389 0.01037 0.00919 AFIX 43 H00V 2 0.294692 0.497285 0.506145 0.11492 -1.20000 AFIX 0 HKLF 4 REM crx-440_a.res in P-1 REM R1 = 0.1268 for 2932 Fo > 4sig(Fo) and 0.1417 for all 3536 data REM 274 parameters refined using 27 restraints END WGHT 0.1772 7.6562 REM Highest difference peak 4.425, deepest hole -1.564, 1-sigma level 0.150 Q1 1 0.4341 0.1214 0.1615 11.00000 0.05 4.42 Q2 1 0.7219 0.2989 0.2523 11.00000 0.05 1.83 Q3 1 0.2206 0.3457 0.4957 11.00000 0.05 1.74 Q4 1 0.0659 0.2823 0.4704 11.00000 0.05 1.28 Q5 1 0.5926 0.2865 0.2646 11.00000 0.05 0.98 Q6 1 0.3072 0.2166 0.6578 11.00000 0.05 0.80 Q7 1 0.2579 0.0828 0.1643 11.00000 0.05 0.75 Q8 1 0.2802 0.2953 0.6418 11.00000 0.05 0.71 Q9 1 -0.0197 0.3291 0.4708 11.00000 0.05 0.64 Q10 1 0.0305 0.4493 0.3444 11.00000 0.05 0.62 Q11 1 0.1625 0.2611 0.5655 11.00000 0.05 0.60 Q12 1 0.1187 0.2783 0.6181 11.00000 0.05 0.58 Q13 1 0.3025 0.4218 0.4704 11.00000 0.05 0.57 Q14 1 0.1561 0.4806 0.3458 11.00000 0.05 0.50 Q15 1 0.4214 0.1785 0.0628 11.00000 0.05 0.48 Q16 1 0.2024 0.5067 0.5187 11.00000 0.05 0.47 Q17 1 0.0824 0.3839 0.2770 11.00000 0.05 0.47 Q18 1 0.1267 0.5977 0.2184 11.00000 0.05 0.47 Q19 1 0.3050 0.6228 0.1054 11.00000 0.05 0.46 Q20 1 0.6121 0.2667 0.3834 11.00000 0.05 0.44 REM The information below was added by Olex2. REM REM R1 = 0.1268 for 2932 Fo > 4sig(Fo) and 0.1417 for all 13318 data REM n/a parameters refined using n/a restraints REM Highest difference peak 4.42, deepest hole -1.56 REM Mean Shift 0, Max Shift 0.006. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1417 REM R1_gt = 0.1268 REM wR_ref = 0.3380 REM GOOF = 1.074 REM Shift_max = 0.006 REM Shift_mean = 0 REM Reflections_all = 13318 REM Reflections_gt = 2932 REM Parameters = n/a REM Hole = -1.56 REM Peak = 4.42 REM Flack = n/a ; _cod_data_source_file d0cc00135j2.cif _cod_data_source_block crx-440 _cod_depositor_comments 'Adding full bibliography for 7126494.cif.' _cod_database_code 7126494 _shelx_shelxl_version_number 2017/1 _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 0.974 _shelx_estimated_absorpt_t_min 0.970 _reflns_odcompleteness_completeness 99.98 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Rigid bond restraints C14, O5 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 S1, C19 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 O5, C15 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 3. Uiso/Uaniso restraints and constraints C14 \\sim O5: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 S1 \\sim C19: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 O5 \\sim C15: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004 Uanis(C19) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2 4. Others Sof(H12A)=Sof(H12B)=Sof(H14A)=Sof(C00V)=1-FVAR(1) Sof(H14)=Sof(C13)=FVAR(1) 5.a Secondary CH2 refined with riding coordinates: C17(H17A,H17B), C18(H18A,H18B), C7(H7A,H7B), C16(H16A,H16B), C15(H15A,H15B), C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B) 5.b Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C3(H3), C14(H14), C14(H14A), C13(H13), C00V(H00V) ; _olex2_date_sample_data_collection 2018-02-26 _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.463 _oxdiff_exptl_absorpt_empirical_full_min 0.608 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 S1 S 0.47341(13) 0.23778(12) 0.25148(10) 0.0260(3) Uani 1 1 d . U . . . F3 F 0.4469(4) 0.1163(3) 0.0366(3) 0.0410(8) Uani 1 1 d . . . . . F1 F 0.5136(4) 0.0075(3) 0.1851(3) 0.0432(8) Uani 1 1 d . . . . . O6 O 0.3088(3) -0.0085(3) 0.3479(3) 0.0228(7) Uani 1 1 d . . . . . O3 O 0.2269(3) 0.2831(3) 0.0608(3) 0.0244(8) Uani 1 1 d . . . . . O2 O 0.5144(4) 0.3718(3) 0.2164(3) 0.0261(8) Uani 1 1 d . . . . . O1 O 0.5541(4) 0.2337(4) 0.3723(3) 0.0313(8) Uani 1 1 d . . . . . F2 F 0.6828(4) 0.1926(4) 0.1579(4) 0.0529(9) Uani 1 1 d . . . . . O4 O 0.1613(4) 0.5892(4) 0.1820(4) 0.0407(10) Uani 1 1 d . . . . . O5 O 0.1509(5) 0.2677(4) 0.5952(3) 0.0457(8) Uani 1 1 d . U . . . C2 C 0.0422(5) -0.0259(4) 0.2492(4) 0.0212(10) Uani 1 1 d . . . . . H2 H 0.000566 -0.096710 0.289953 0.025 Uiso 1 1 calc R . . . . C4 C 0.0010(5) 0.1256(5) 0.1040(4) 0.0217(10) Uani 1 1 d . . . . . H4 H -0.068743 0.155333 0.049684 0.026 Uiso 1 1 calc R . . . . C3 C -0.0552(5) 0.0208(5) 0.1670(4) 0.0245(11) Uani 1 1 d . . . . . H3 H -0.163391 -0.019451 0.153101 0.029 Uiso 1 1 calc R . . . . C5 C 0.1631(5) 0.1866(5) 0.1222(4) 0.0218(10) Uani 1 1 d . . . . . C1 C 0.2048(5) 0.0343(5) 0.2710(4) 0.0220(10) Uani 1 1 d . . . . . C17 C 0.2211(5) 0.0117(5) 0.5305(4) 0.0229(10) Uani 1 1 d . . . . . H17A H 0.208305 -0.033669 0.599798 0.027 Uiso 1 1 calc R . . . . H17B H 0.121290 0.020450 0.490226 0.027 Uiso 1 1 calc R . . . . C18 C 0.2619(5) -0.0790(5) 0.4434(4) 0.0282(11) Uani 1 1 d . . . . . H18A H 0.346859 -0.106510 0.488194 0.034 Uiso 1 1 calc R . . . . H18B H 0.171242 -0.162904 0.407344 0.034 Uiso 1 1 calc R . . . . C6 C 0.2663(5) 0.1457(5) 0.2112(4) 0.0256(11) Uani 1 1 d . . . . . C7 C 0.1283(5) 0.3492(5) -0.0119(4) 0.0275(11) Uani 1 1 d . . . . . H7A H 0.065127 0.376507 0.033715 0.033 Uiso 1 1 calc R . . . . H7B H 0.058589 0.285673 -0.085446 0.033 Uiso 1 1 calc R . . . . C16 C 0.3444(6) 0.1562(7) 0.5753(5) 0.0427(16) Uani 1 1 d . . . . . H16A H 0.365741 0.197238 0.505647 0.051 Uiso 1 1 calc R . . . . H16B H 0.441153 0.147632 0.623045 0.051 Uiso 1 1 calc R . . . . C15 C 0.2975(8) 0.2541(6) 0.6520(5) 0.0450(10) Uani 1 1 d . U . . . H15A H 0.292475 0.220455 0.727735 0.054 Uiso 1 1 calc R . . . . H15B H 0.378907 0.345459 0.671622 0.054 Uiso 1 1 calc R . . . . C19 C 0.5279(6) 0.1293(5) 0.1515(4) 0.0290(6) Uani 1 1 d . U . A 1 C8 C 0.2388(6) 0.4756(6) -0.0425(5) 0.0477(14) Uani 1 1 d . . . . . H8A H 0.176613 0.519605 -0.094631 0.057 Uiso 1 1 calc R . . . . H8B H 0.299745 0.444943 -0.088329 0.057 Uiso 1 1 calc R . . . . C10 C 0.2762(7) 0.6665(6) 0.1284(7) 0.059(2) Uani 1 1 d . . . . . H10A H 0.358718 0.737861 0.191346 0.071 Uiso 1 1 calc R . . . . H10B H 0.227058 0.713449 0.069568 0.071 Uiso 1 1 calc R . . . . C9 C 0.3512(6) 0.5832(6) 0.0658(7) 0.0567(18) Uani 1 1 d . . . . . H9A H 0.400869 0.536415 0.124472 0.068 Uiso 1 1 calc R . . . . H9B H 0.433217 0.647062 0.039318 0.068 Uiso 1 1 calc R . . . . C11 C 0.2246(9) 0.5510(6) 0.2940(6) 0.063(2) Uani 1 1 d . . . . . H11A H 0.284800 0.633703 0.354983 0.076 Uiso 1 1 calc R . . . . H11B H 0.294201 0.501008 0.283865 0.076 Uiso 1 1 calc R . . . . C12 C 0.0925(13) 0.4611(6) 0.3331(6) 0.084(3) Uani 1 1 d . . . . . H12A H 0.031372 0.375838 0.275231 0.101 Uiso 0.539(11) 1 calc R . P B 2 H12B H 0.023784 0.509573 0.348857 0.101 Uiso 0.539(11) 1 calc R . P B 2 C14 C 0.1359(11) 0.3148(7) 0.4819(6) 0.0675(17) Uani 1 1 d . U . . . H14 H 0.164912 0.273587 0.421054 0.081 Uiso 0.461(11) 1 calc R . P B 1 H14A H 0.069279 0.247869 0.414884 0.081 Uiso 0.539(11) 1 calc R . P B 2 C13 C 0.0823(12) 0.4143(10) 0.4633(9) 0.024(2) Uani 0.461(11) 1 d . . P B 1 H13 H 0.042800 0.454433 0.517264 0.029 Uiso 0.08(11) 1 calc R . . B 1 C00V C 0.1990(10) 0.4331(10) 0.4583(8) 0.027(2) Uani 0.539(11) 1 d . . P B 2 H00V H 0.294692 0.497285 0.506145 0.033 Uiso 0.11(12) 1 calc R . . B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0272(5) 0.0270(5) 0.0247(5) 0.0082(4) 0.0058(4) 0.0110(4) F3 0.0442(15) 0.0549(18) 0.0283(14) 0.0057(13) 0.0172(11) 0.0183(13) F1 0.0533(16) 0.0272(13) 0.0623(19) 0.0184(13) 0.0289(14) 0.0197(12) O6 0.0240(13) 0.0327(15) 0.0233(14) 0.0177(12) 0.0128(11) 0.0175(11) O3 0.0181(13) 0.0347(16) 0.0219(14) 0.0168(12) 0.0027(11) 0.0110(11) O2 0.0235(14) 0.0237(14) 0.0337(17) 0.0139(13) 0.0077(12) 0.0101(11) O1 0.0212(14) 0.0542(19) 0.0213(15) 0.0166(14) 0.0021(12) 0.0176(13) F2 0.0391(15) 0.0530(18) 0.081(2) 0.0197(17) 0.0335(14) 0.0211(13) O4 0.0405(19) 0.0289(16) 0.039(2) 0.0064(15) -0.0150(17) 0.0145(14) O5 0.0767(15) 0.0333(13) 0.0230(12) 0.0069(11) 0.0074(12) 0.0183(12) C2 0.0229(19) 0.0188(19) 0.022(2) 0.0047(16) 0.0102(16) 0.0040(16) C4 0.0183(19) 0.033(2) 0.0129(19) 0.0066(17) 0.0018(15) 0.0091(16) C3 0.020(2) 0.028(2) 0.017(2) -0.0001(18) 0.0007(16) 0.0028(17) C5 0.0175(18) 0.030(2) 0.020(2) 0.0080(17) 0.0055(16) 0.0093(16) C1 0.0240(19) 0.027(2) 0.0192(19) 0.0070(17) 0.0085(16) 0.0124(16) C17 0.0208(19) 0.032(2) 0.0173(19) 0.0126(17) 0.0040(16) 0.0109(16) C18 0.0241(19) 0.037(2) 0.036(2) 0.0237(18) 0.0158(17) 0.0182(16) C6 0.0196(19) 0.037(2) 0.027(2) 0.0162(18) 0.0102(16) 0.0143(16) C7 0.021(2) 0.042(2) 0.022(2) 0.0188(18) 0.0010(17) 0.0152(17) C16 0.027(2) 0.055(3) 0.028(3) -0.004(2) 0.008(2) -0.008(2) C15 0.0713(17) 0.0356(15) 0.0218(14) 0.0055(14) 0.0112(14) 0.0118(15) C19 0.0313(8) 0.0277(8) 0.0262(8) 0.0081(8) 0.0043(8) 0.0100(8) C8 0.031(2) 0.073(3) 0.062(3) 0.055(2) 0.025(2) 0.029(2) C10 0.028(3) 0.023(2) 0.102(5) 0.034(3) -0.016(3) -0.001(2) C9 0.015(2) 0.045(3) 0.110(5) 0.055(3) 0.007(3) 0.0084(19) C11 0.098(4) 0.030(2) 0.039(3) -0.008(2) -0.036(3) 0.037(2) C12 0.176(8) 0.026(3) 0.025(3) 0.003(2) -0.008(4) 0.029(4) C14 0.123(3) 0.046(3) 0.031(2) 0.008(2) 0.008(3) 0.037(3) C13 0.030(5) 0.023(4) 0.027(5) 0.009(4) 0.011(4) 0.016(3) C00V 0.024(4) 0.034(4) 0.025(4) 0.004(4) 0.010(3) 0.009(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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 O2 S1 C6 113.7(2) . . ? O2 S1 C19 106.0(2) . . ? O1 S1 O2 115.2(2) . . ? O1 S1 C6 113.6(2) . . ? O1 S1 C19 106.8(2) . . ? C6 S1 C19 99.8(2) . . ? C1 O6 C18 119.0(3) . . ? C5 O3 C7 119.0(3) . . ? C11 O4 C10 114.5(5) . . ? C14 O5 C15 116.6(6) . . ? C3 C2 H2 120.5 . . ? C3 C2 C1 119.1(4) . . ? C1 C2 H2 120.5 . . ? C3 C4 H4 120.1 . . ? C3 C4 C5 119.7(4) . . ? C5 C4 H4 120.1 . . ? C2 C3 C4 122.6(4) . . ? C2 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? O3 C5 C4 123.6(4) . . ? O3 C5 C6 117.6(4) . . ? C4 C5 C6 118.7(4) . . ? O6 C1 C2 122.8(4) . . ? O6 C1 C6 117.6(4) . . ? C2 C1 C6 119.6(4) . . ? H17A C17 H17B 107.7 . . ? C18 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? C18 C17 C16 113.3(4) . . ? C16 C17 H17A 108.9 . . ? C16 C17 H17B 108.9 . . ? O6 C18 C17 112.3(4) . . ? O6 C18 H18A 109.1 . . ? O6 C18 H18B 109.1 . . ? C17 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C5 C6 S1 119.9(3) . . ? C5 C6 C1 120.0(4) . . ? C1 C6 S1 120.1(3) . . ? O3 C7 H7A 110.5 . . ? O3 C7 H7B 110.5 . . ? O3 C7 C8 106.4(4) . . ? H7A C7 H7B 108.6 . . ? C8 C7 H7A 110.5 . . ? C8 C7 H7B 110.5 . . ? C17 C16 H16A 108.7 . . ? C17 C16 H16B 108.7 . . ? C17 C16 C15 114.1(5) . . ? H16A C16 H16B 107.6 . . ? C15 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? O5 C15 C16 114.3(4) . . ? O5 C15 H15A 108.7 . . ? O5 C15 H15B 108.7 . . ? C16 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? F3 C19 S1 111.1(4) . . ? F3 C19 F2 106.3(4) . . ? F1 C19 S1 111.4(4) . . ? F1 C19 F3 111.8(4) . . ? F1 C19 F2 107.0(4) . . ? F2 C19 S1 109.0(3) . . ? C7 C8 H8A 108.5 . . ? C7 C8 H8B 108.5 . . ? C7 C8 C9 115.0(5) . . ? H8A C8 H8B 107.5 . . ? C9 C8 H8A 108.5 . . ? C9 C8 H8B 108.5 . . ? O4 C10 H10A 108.3 . . ? O4 C10 H10B 108.3 . . ? O4 C10 C9 115.8(4) . . ? H10A C10 H10B 107.4 . . ? C9 C10 H10A 108.3 . . ? C9 C10 H10B 108.3 . . ? C8 C9 H9A 108.6 . . ? C8 C9 H9B 108.6 . . ? C10 C9 C8 114.7(5) . . ? C10 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? O4 C11 H11A 110.0 . . ? O4 C11 H11B 110.0 . . ? O4 C11 C12 108.4(6) . . ? H11A C11 H11B 108.4 . . ? C12 C11 H11A 110.0 . . ? C12 C11 H11B 110.0 . . ? C11 C12 H12A 112.3 . . ? C11 C12 H12B 112.3 . . ? C11 C12 C13 132.0(7) . . ? C11 C12 C00V 97.2(7) . . ? H12A C12 H12B 109.9 . . ? C00V C12 H12A 112.3 . . ? C00V C12 H12B 112.3 . . ? O5 C14 H14 120.0 . . ? O5 C14 H14A 115.1 . . ? C13 C14 O5 120.0(8) . . ? C13 C14 H14 120.0 . . ? C00V C14 O5 129.8(7) . . ? C00V C14 H14A 115.1 . . ? C12 C13 H13 124.4 . . ? C14 C13 C12 111.3(9) . . ? C14 C13 H13 124.4 . . ? C12 C00V H00V 124.0 . . ? C14 C00V C12 111.9(7) . . ? C14 C00V H00V 124.0 . . ? 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 S1 O2 1.426(3) . ? S1 O1 1.421(3) . ? S1 C6 1.786(4) . ? S1 C19 1.811(6) . ? F3 C19 1.326(6) . ? F1 C19 1.314(6) . ? O6 C1 1.353(5) . ? O6 C18 1.446(6) . ? O3 C5 1.335(6) . ? O3 C7 1.455(6) . ? F2 C19 1.368(6) . ? O4 C10 1.426(8) . ? O4 C11 1.421(7) . ? O5 C15 1.422(8) . ? O5 C14 1.418(8) . ? C2 H2 0.9300 . ? C2 C3 1.372(7) . ? C2 C1 1.397(6) . ? C4 H4 0.9300 . ? C4 C3 1.384(7) . ? C4 C5 1.399(6) . ? C3 H3 0.9300 . ? C5 C6 1.412(6) . ? C1 C6 1.421(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 C18 1.513(7) . ? C17 C16 1.516(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.510(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 C15 1.523(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.512(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C9 1.510(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.484(13) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.627(12) . ? C12 C00V 1.642(12) . ? C14 H14 0.9300 . ? C14 H14A 0.9300 . ? C14 C13 1.284(13) . ? C14 C00V 1.255(12) . ? C13 H13 0.9300 . ? C00V H00V 0.9300 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O6 C1 C6 S1 -7.3(6) . . . . ? O6 C1 C6 C5 174.5(4) . . . . ? O3 C5 C6 S1 7.8(6) . . . . ? O3 C5 C6 C1 -174.0(4) . . . . ? O3 C7 C8 C9 -61.2(6) . . . . ? O2 S1 C6 C5 18.0(5) . . . . ? O2 S1 C6 C1 -160.1(4) . . . . ? O2 S1 C19 F3 -62.5(4) . . . . ? O2 S1 C19 F1 172.1(3) . . . . ? O2 S1 C19 F2 54.3(4) . . . . ? O1 S1 C6 C5 152.4(4) . . . . ? O1 S1 C6 C1 -25.8(5) . . . . ? O1 S1 C19 F3 174.3(3) . . . . ? O1 S1 C19 F1 48.8(4) . . . . ? O1 S1 C19 F2 -68.9(4) . . . . ? O4 C10 C9 C8 63.3(7) . . . . ? O4 C11 C12 C13 -163.7(8) . . . . ? O4 C11 C12 C00V 179.1(5) . . . . ? O5 C14 C13 C12 174.2(7) . . . . ? O5 C14 C00V C12 -153.5(9) . . . . ? C2 C1 C6 S1 172.4(4) . . . . ? C2 C1 C6 C5 -5.8(7) . . . . ? C4 C5 C6 S1 -171.5(4) . . . . ? C4 C5 C6 C1 6.7(7) . . . . ? C3 C2 C1 O6 -178.0(4) . . . . ? C3 C2 C1 C6 2.3(7) . . . . ? C3 C4 C5 O3 176.5(4) . . . . ? C3 C4 C5 C6 -4.2(7) . . . . ? C5 O3 C7 C8 165.7(4) . . . . ? C5 C4 C3 C2 0.8(7) . . . . ? C1 O6 C18 C17 -61.3(5) . . . . ? C1 C2 C3 C4 0.2(7) . . . . ? C17 C16 C15 O5 -54.2(7) . . . . ? C18 O6 C1 C2 -23.6(6) . . . . ? C18 O6 C1 C6 156.1(4) . . . . ? C18 C17 C16 C15 173.7(4) . . . . ? C6 S1 C19 F3 55.8(4) . . . . ? C6 S1 C19 F1 -69.6(4) . . . . ? C6 S1 C19 F2 172.6(3) . . . . ? C7 O3 C5 C4 12.4(7) . . . . ? C7 O3 C5 C6 -166.9(4) . . . . ? C7 C8 C9 C10 -72.7(7) . . . . ? C16 C17 C18 O6 -48.9(5) . . . . ? C15 O5 C14 C13 -131.1(8) . . . . ? C15 O5 C14 C00V -70.8(12) . . . . ? C19 S1 C6 C5 -94.4(4) . . . . ? C19 S1 C6 C1 87.5(4) . . . . ? C10 O4 C11 C12 -175.0(5) . . . . ? C11 O4 C10 C9 76.8(6) . . . . ? C11 C12 C13 C14 -79.7(11) . . . . ? C11 C12 C00V C14 -147.7(8) . . . . ? C14 O5 C15 C16 -57.8(6) . . . . ?