#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:27:53 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252908 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157453.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_7157453 loop_ _publ_author_name 'Wu, Xinjie' 'Jia, Ming' 'Huang, Mengmeng' 'Kim, Jung Keun' 'Zhao, Zheng' 'Liu, Junkai' 'Xi, Jinhu' 'Li, Yabo' 'Wu, Yangjie' _publ_section_title ; A visible-light-induced "on-off" one-pot synthesis of 3-arylacetylene coumarins with AIE properties. ; _journal_issue 17 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3346 _journal_page_last 3353 _journal_paper_doi 10.1039/d0ob00479k _journal_volume 18 _journal_year 2020 _chemical_formula_moiety 'C24 H13 F3 O2' _chemical_formula_sum 'C24 H13 F3 O2' _chemical_formula_weight 390.34 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-11-07 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-11-20 deposited with the CCDC. 2020-04-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 110.026(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.8769(8) _cell_length_b 11.8650(6) _cell_length_c 14.2912(11) _cell_measurement_reflns_used 1789 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 69.6380 _cell_measurement_theta_min 3.9470 _cell_volume 1892.1(2) _computing_cell_refinement 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 -85.00 -5.00 1.00 2.50 -- -33.50 -77.00 -30.00 80 2 \w -41.00 -15.00 1.00 2.50 -- -33.50 -57.00-180.00 26 3 \w -88.00 -43.00 1.00 2.50 -- -33.50 -57.00 120.00 45 4 \w -93.00 -60.00 1.00 2.50 -- -33.50 -57.00-180.00 33 5 \w 62.00 87.00 1.00 2.50 -- 36.47 178.00-120.00 25 6 \w 77.00 102.00 1.00 2.50 -- 36.47 178.00 -60.00 25 7 \w 58.00 109.00 1.00 2.50 -- 36.47 178.00-180.00 51 8 \w 58.00 102.00 1.00 2.50 -- 36.47 178.00 90.00 44 9 \w -27.00 46.00 1.00 2.50 -- 36.47 -57.00-120.00 73 10 \w 88.00 172.00 1.00 10.00 -- 108.00 45.00 150.00 84 11 \w 112.00 141.00 1.00 10.00 -- 108.00 77.00-120.00 29 12 \w 43.00 70.00 1.00 10.00 -- 108.00 -77.00 0.00 27 13 \w 42.00 120.00 1.00 10.00 -- 108.00 -45.00 0.00 78 14 \w 84.00 134.00 1.00 10.00 -- 108.00 -30.00 120.00 50 15 \w 37.00 63.00 1.00 10.00 -- 108.00 -30.00 120.00 26 16 \w 50.00 109.00 1.00 10.00 -- 108.00 -94.00-180.00 59 17 \w 71.00 109.00 1.00 10.00 -- 108.00 -77.00 0.00 38 18 \w 43.00 96.00 1.00 10.00 -- 108.00 -94.00 -30.00 53 19 \w 110.00 143.00 1.00 10.00 -- 108.00 178.00 30.00 33 20 \w 60.00 98.00 1.00 10.00 -- 108.00 178.00 30.00 38 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1280686000 _diffrn_orient_matrix_UB_12 0.0430326000 _diffrn_orient_matrix_UB_13 -0.0175468000 _diffrn_orient_matrix_UB_21 0.0011211000 _diffrn_orient_matrix_UB_22 0.0633881000 _diffrn_orient_matrix_UB_23 -0.0937611000 _diffrn_orient_matrix_UB_31 -0.0514381000 _diffrn_orient_matrix_UB_32 -0.1048471000 _diffrn_orient_matrix_UB_33 -0.0637929000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_unetI/netI 0.0304 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 7164 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.063 _diffrn_reflns_theta_max 67.063 _diffrn_reflns_theta_min 3.962 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.902 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.76891 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.370 _exptl_crystal_description block _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.327 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.042 _refine_ls_extinction_coef 0.0013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 273 _refine_ls_number_reflns 3371 _refine_ls_number_restraints 67 _refine_ls_restrained_S_all 1.133 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0605 _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^)+(0.0872P)^2^+0.6254P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1653 _refine_ls_wR_factor_ref 0.1862 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2485 _reflns_number_total 3371 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201911285.res created by SHELXL-2014/7 TITL 201911285 in P21/c #14 REM reset to P21/c #14 CELL 1.54184 11.876903 11.865016 14.291228 90 110.0257 90 ZERR 4 0.000848 0.000641 0.001071 0 0.0082 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F O UNIT 96 52 12 8 DFIX 1.35 F3A C24 SADI 0.04 F3 F1 F3 F2 F1 F2 F1A F2A F1A F3A F2A F3A SADI C24 F3 C24 F1 C24 F2 C24 F1A C24 F2A C24 F3A ISOR 0.01 0.02 F3 F1A F2 F2A F1 F3A EADP F1 F1A EADP F2 F2A EADP F3 F3A L.S. 16 0 0 PLAN 20 SIZE 0.1 0.11 0.12 MPLA C1 C2 C3 C4 C5 C6 C7 C8 C9 O2 MPLA C10 C11 C12 C13 C14 C15 MPLA C18 C19 C20 C21 C22 C23 BOND $h conf fmap 2 acta REM REM REM WGHT 0.087200 0.625400 EXTI 0.001271 FVAR 4.15995 0.68604 C1 1 0.190497 0.563259 0.695279 11.00000 0.06494 0.04887 = 0.05746 0.00590 0.02314 0.00249 C2 1 0.064405 0.597379 0.647104 11.00000 0.06051 0.04675 = 0.05332 -0.00023 0.02440 -0.00213 C3 1 0.032471 0.708257 0.633617 11.00000 0.05382 0.04873 = 0.05258 -0.00180 0.02087 -0.00218 C4 1 0.124795 0.793232 0.668181 11.00000 0.05354 0.04809 = 0.05598 -0.00176 0.02162 -0.00214 C5 1 0.242829 0.758549 0.716484 11.00000 0.05681 0.05176 = 0.05383 0.00052 0.01967 -0.00065 C6 1 0.335290 0.833691 0.754747 11.00000 0.05443 0.06548 = 0.06874 0.00042 0.01418 -0.00478 AFIX 43 H6 2 0.412885 0.808005 0.787274 11.00000 -1.20000 AFIX 0 C7 1 0.311690 0.946998 0.744358 11.00000 0.06355 0.06136 = 0.07740 -0.00501 0.01673 -0.01137 C8 1 0.196428 0.985489 0.693749 11.00000 0.07009 0.04899 = 0.09714 -0.00674 0.02362 -0.00978 AFIX 43 H8 2 0.181338 1.062406 0.685214 11.00000 -1.20000 AFIX 0 C9 1 0.104762 0.909379 0.656337 11.00000 0.05496 0.04915 = 0.08194 -0.00041 0.01801 -0.00089 AFIX 43 H9 2 0.027758 0.935643 0.622417 11.00000 -1.20000 AFIX 0 C10 1 -0.095353 0.740433 0.583432 11.00000 0.05366 0.04470 = 0.06157 -0.00203 0.02039 -0.00453 C11 1 -0.156395 0.803276 0.632803 11.00000 0.06030 0.05323 = 0.07167 -0.00797 0.02367 -0.00426 AFIX 43 H11 2 -0.116725 0.827987 0.697519 11.00000 -1.20000 AFIX 0 C12 1 -0.276300 0.829168 0.585728 11.00000 0.05985 0.06436 = 0.09488 -0.00991 0.03156 0.00018 AFIX 43 H12 2 -0.317357 0.869951 0.619437 11.00000 -1.20000 AFIX 0 C13 1 -0.334405 0.795077 0.490107 11.00000 0.05319 0.07323 = 0.09658 -0.00356 0.01729 -0.00116 AFIX 43 H13 2 -0.414396 0.814257 0.458391 11.00000 -1.20000 AFIX 0 C14 1 -0.275023 0.732229 0.440182 11.00000 0.06313 0.07850 = 0.07316 -0.00739 0.01283 -0.00096 AFIX 43 H14 2 -0.315103 0.708846 0.375124 11.00000 -1.20000 AFIX 0 C15 1 -0.156396 0.704214 0.486829 11.00000 0.06021 0.06154 = 0.06527 -0.00483 0.02045 -0.00153 AFIX 43 H15 2 -0.116927 0.660816 0.453489 11.00000 -1.20000 AFIX 0 C16 1 -0.017957 0.506408 0.618769 11.00000 0.06541 0.04649 = 0.06121 0.00230 0.02738 0.00144 C17 1 -0.083763 0.426498 0.596101 11.00000 0.06415 0.04873 = 0.05988 0.00322 0.02705 -0.00107 C18 1 -0.162346 0.332098 0.566061 11.00000 0.06332 0.04681 = 0.05598 0.00207 0.02621 -0.00496 C19 1 -0.282599 0.347613 0.510976 11.00000 0.06476 0.06301 = 0.07727 0.01358 0.02335 0.00452 AFIX 43 H19 2 -0.312622 0.419946 0.493555 11.00000 -1.20000 AFIX 0 C20 1 -0.357474 0.255885 0.482110 11.00000 0.06395 0.09172 = 0.08657 0.01233 0.01418 -0.01370 AFIX 43 H20 2 -0.437969 0.266922 0.445047 11.00000 -1.20000 AFIX 0 C21 1 -0.315616 0.149355 0.506924 11.00000 0.08478 0.07079 = 0.08739 -0.00447 0.02949 -0.02965 AFIX 43 H21 2 -0.367164 0.088076 0.487116 11.00000 -1.20000 AFIX 0 C22 1 -0.196583 0.132884 0.561488 11.00000 0.09391 0.04531 = 0.09295 0.00306 0.04145 -0.00328 AFIX 43 H22 2 -0.167663 0.060144 0.578537 11.00000 -1.20000 AFIX 0 C23 1 -0.120083 0.223034 0.590997 11.00000 0.06547 0.05344 = 0.07480 0.00724 0.02875 0.00277 AFIX 43 H23 2 -0.039676 0.211061 0.627814 11.00000 -1.20000 AFIX 0 C24 1 0.411431 1.027397 0.786979 11.00000 0.08025 0.07353 = 0.13327 -0.00429 0.00684 -0.02053 PART 1 F1 3 0.472439 1.039292 0.721304 21.00000 0.11213 0.15637 = 0.19119 -0.03601 0.05910 -0.07945 PART 0 PART 2 F1A 3 0.404762 1.065184 0.880322 -21.00000 0.11213 0.15637 = 0.19119 -0.03601 0.05910 -0.07945 PART 0 PART 1 F2 3 0.492738 0.994699 0.869287 21.00000 0.11959 0.12528 = 0.14306 0.01213 -0.05308 -0.04660 PART 0 PART 2 F2A 3 0.516933 0.988784 0.817702 -21.00000 0.11959 0.12528 = 0.14306 0.01213 -0.05308 -0.04660 PART 0 PART 1 F3 3 0.377698 1.134504 0.789586 21.00000 0.12251 0.07976 = 0.16662 -0.03032 0.01177 -0.03345 PART 0 PART 2 F3A 3 0.410366 1.117807 0.744971 -21.00000 0.12251 0.07976 = 0.16662 -0.03032 0.01177 -0.03345 PART 0 O1 4 0.225467 0.467973 0.707945 11.00000 0.07794 0.05376 = 0.09051 0.01089 0.02525 0.01243 O2 4 0.273355 0.646750 0.729193 11.00000 0.05647 0.05454 = 0.07034 0.00433 0.01770 0.00365 HKLF 4 REM 201911285 in P21/c #14 REM R1 = 0.0605 for 2485 Fo > 4sig(Fo) and 0.0800 for all 3371 data REM 273 parameters refined using 67 restraints END WGHT 0.0872 0.6253 REM Highest difference peak 0.327, deepest hole -0.441, 1-sigma level 0.042 Q1 1 0.3650 1.1026 0.8493 11.00000 0.05 0.33 Q2 1 0.3623 1.0613 0.8901 11.00000 0.05 0.30 Q3 1 0.4755 1.0105 0.6723 11.00000 0.05 0.25 Q4 1 0.5001 0.9844 0.7643 11.00000 0.05 0.22 Q5 1 0.4502 1.0827 0.7391 11.00000 0.05 0.20 Q6 1 -0.0749 0.4942 0.6218 11.00000 0.05 0.17 Q7 1 0.0443 0.6497 0.6677 11.00000 0.05 0.16 Q8 1 0.1800 0.7803 0.6590 11.00000 0.05 0.15 Q9 1 0.1204 0.8371 0.6342 11.00000 0.05 0.15 Q10 1 0.3407 0.9035 0.7111 11.00000 0.05 0.14 Q11 1 -0.1549 0.2842 0.6076 11.00000 0.05 0.13 Q12 1 -0.0170 0.4204 0.6210 11.00000 0.05 0.13 Q13 1 0.0639 0.6616 0.6059 11.00000 0.05 0.12 Q14 1 -0.3250 0.6579 0.3849 11.00000 0.05 0.11 Q15 1 -0.1473 0.7200 0.6250 11.00000 0.05 0.11 Q16 1 0.0082 0.2186 0.6033 11.00000 0.05 0.11 Q17 1 -0.0358 0.7142 0.6193 11.00000 0.05 0.11 Q18 1 0.3661 0.9464 0.8906 11.00000 0.05 0.11 Q19 1 -0.1505 0.2778 0.5400 11.00000 0.05 0.10 Q20 1 -0.3383 0.7110 0.4736 11.00000 0.05 0.10 REM The information below was added by Olex2. REM REM R1 = 0.0605 for 2485 Fo > 4sig(Fo) and 0.0800 for all 7422 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.33, deepest hole -0.44 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0800 REM R1_gt = 0.0605 REM wR_ref = 0.1862 REM GOOF = 1.040 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 7422 REM Reflections_gt = 2485 REM Parameters = n/a REM Hole = -0.44 REM Peak = 0.33 REM Flack = n/a ; _cod_data_source_file d0ob00479k2.cif _cod_data_source_block 201911285 _cod_depositor_comments 'Adding full bibliography for 7157451--7157455.cif.' _cod_original_cell_volume 1892.2(2) _cod_database_code 7157453 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C40H40O2N4F3 _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 0.915 _shelx_estimated_absorpt_t_min 0.899 _reflns_odcompleteness_completeness 99.86 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2. Restrained distances F3A-C24 1.35 with sigma of 0.02 F3-F1 \\sim F3-F2 \\sim F1-F2 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A with sigma of 0.04 C24-F3 \\sim C24-F1 \\sim C24-F2 \\sim C24-F1A \\sim C24-F2A \\sim C24-F3A with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(F3) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(F1) = Uanis(F1A) Uanis(F2) = Uanis(F2A) Uanis(F3) = Uanis(F3A) 4. Others Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1) Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1) 5.a Aromatic/amide H refined with riding coordinates: C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23) ; _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 1.395 _oxdiff_exptl_absorpt_empirical_full_min 0.827 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1905(2) 0.5633(2) 0.69528(19) 0.0565(6) Uani 1 1 d . . . . . C2 C 0.0644(2) 0.5974(2) 0.64710(18) 0.0523(6) Uani 1 1 d . . . . . C3 C 0.0325(2) 0.7083(2) 0.63362(18) 0.0510(6) Uani 1 1 d . . . . . C4 C 0.1248(2) 0.7932(2) 0.66818(18) 0.0518(6) Uani 1 1 d . . . . . C5 C 0.2428(2) 0.7585(2) 0.71648(18) 0.0539(6) Uani 1 1 d . . . . . C6 C 0.3353(3) 0.8337(2) 0.7547(2) 0.0647(7) Uani 1 1 d . . . . . H6 H 0.4129 0.8080 0.7873 0.078 Uiso 1 1 calc R . . . . C7 C 0.3117(3) 0.9470(3) 0.7444(2) 0.0694(8) Uani 1 1 d . . . . . C8 C 0.1964(3) 0.9855(2) 0.6937(3) 0.0734(8) Uani 1 1 d . . . . . H8 H 0.1813 1.0624 0.6852 0.088 Uiso 1 1 calc R . . . . C9 C 0.1048(3) 0.9094(2) 0.6563(2) 0.0634(7) Uani 1 1 d . . . . . H9 H 0.0278 0.9356 0.6224 0.076 Uiso 1 1 calc R . . . . C10 C -0.0954(2) 0.7404(2) 0.58343(19) 0.0531(6) Uani 1 1 d . . . . . C11 C -0.1564(2) 0.8033(2) 0.6328(2) 0.0615(7) Uani 1 1 d . . . . . H11 H -0.1167 0.8280 0.6975 0.074 Uiso 1 1 calc R . . . . C12 C -0.2763(3) 0.8292(3) 0.5857(3) 0.0717(8) Uani 1 1 d . . . . . H12 H -0.3174 0.8700 0.6194 0.086 Uiso 1 1 calc R . . . . C13 C -0.3344(3) 0.7951(3) 0.4901(3) 0.0765(9) Uani 1 1 d . . . . . H13 H -0.4144 0.8143 0.4584 0.092 Uiso 1 1 calc R . . . . C14 C -0.2750(3) 0.7322(3) 0.4402(2) 0.0743(8) Uani 1 1 d . . . . . H14 H -0.3151 0.7088 0.3751 0.089 Uiso 1 1 calc R . . . . C15 C -0.1564(2) 0.7042(2) 0.4868(2) 0.0626(7) Uani 1 1 d . . . . . H15 H -0.1169 0.6608 0.4535 0.075 Uiso 1 1 calc R . . . . C16 C -0.0180(2) 0.5064(2) 0.61877(19) 0.0562(6) Uani 1 1 d . . . . . C17 C -0.0838(2) 0.4265(2) 0.59610(19) 0.0561(6) Uani 1 1 d . . . . . C18 C -0.1623(2) 0.3321(2) 0.56606(18) 0.0539(6) Uani 1 1 d . . . . . C19 C -0.2826(3) 0.3476(3) 0.5110(2) 0.0686(8) Uani 1 1 d . . . . . H19 H -0.3126 0.4199 0.4936 0.082 Uiso 1 1 calc R . . . . C20 C -0.3575(3) 0.2559(3) 0.4821(3) 0.0837(10) Uani 1 1 d . . . . . H20 H -0.4380 0.2669 0.4450 0.100 Uiso 1 1 calc R . . . . C21 C -0.3156(3) 0.1494(3) 0.5069(3) 0.0810(9) Uani 1 1 d . . . . . H21 H -0.3672 0.0881 0.4871 0.097 Uiso 1 1 calc R . . . . C22 C -0.1966(3) 0.1329(2) 0.5615(2) 0.0749(8) Uani 1 1 d . . . . . H22 H -0.1677 0.0601 0.5785 0.090 Uiso 1 1 calc R . . . . C23 C -0.1201(3) 0.2230(2) 0.5910(2) 0.0633(7) Uani 1 1 d . . . . . H23 H -0.0397 0.2111 0.6278 0.076 Uiso 1 1 calc R . . . . C24 C 0.4114(4) 1.0274(3) 0.7870(4) 0.1034(13) Uani 1 1 d D . . . . F1 F 0.4724(4) 1.0393(5) 0.7213(4) 0.1514(17) Uani 0.686(4) 1 d D U P A 1 F1A F 0.4048(10) 1.0652(11) 0.8803(9) 0.1514(17) Uani 0.314(4) 1 d D U P A 2 F2 F 0.4927(5) 0.9947(6) 0.8693(4) 0.155(3) Uani 0.686(4) 1 d D U P A 1 F2A F 0.5169(11) 0.9888(14) 0.8177(10) 0.155(3) Uani 0.314(4) 1 d D U P A 2 F3 F 0.3777(5) 1.1345(3) 0.7896(4) 0.133(2) Uani 0.686(4) 1 d D U P A 1 F3A F 0.4104(13) 1.1178(8) 0.7450(9) 0.133(2) Uani 0.314(4) 1 d D U P A 2 O1 O 0.22547(19) 0.46797(16) 0.70794(16) 0.0750(6) Uani 1 1 d . . . . . O2 O 0.27335(16) 0.64675(15) 0.72919(14) 0.0615(5) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0649(15) 0.0489(14) 0.0575(13) 0.0059(11) 0.0231(12) 0.0025(12) C2 0.0605(14) 0.0467(13) 0.0533(12) -0.0002(10) 0.0244(11) -0.0021(11) C3 0.0538(14) 0.0487(13) 0.0526(12) -0.0018(10) 0.0209(11) -0.0022(11) C4 0.0535(14) 0.0481(13) 0.0560(13) -0.0018(10) 0.0216(11) -0.0021(10) C5 0.0568(14) 0.0518(14) 0.0538(13) 0.0005(11) 0.0197(11) -0.0006(11) C6 0.0544(15) 0.0655(17) 0.0687(16) 0.0004(13) 0.0142(12) -0.0048(13) C7 0.0636(17) 0.0614(16) 0.0774(18) -0.0050(14) 0.0167(14) -0.0114(14) C8 0.0701(18) 0.0490(15) 0.097(2) -0.0067(15) 0.0236(16) -0.0098(13) C9 0.0550(15) 0.0492(14) 0.0819(17) -0.0004(13) 0.0180(13) -0.0009(11) C10 0.0537(14) 0.0447(12) 0.0616(14) -0.0020(11) 0.0204(11) -0.0045(10) C11 0.0603(16) 0.0532(14) 0.0717(16) -0.0080(12) 0.0237(13) -0.0043(12) C12 0.0599(16) 0.0644(17) 0.095(2) -0.0099(16) 0.0316(15) 0.0002(13) C13 0.0532(16) 0.0732(19) 0.097(2) -0.0036(17) 0.0173(15) -0.0012(14) C14 0.0631(17) 0.079(2) 0.0732(17) -0.0074(15) 0.0128(14) -0.0010(15) C15 0.0602(16) 0.0615(16) 0.0653(15) -0.0048(13) 0.0205(13) -0.0015(12) C16 0.0654(16) 0.0465(14) 0.0612(14) 0.0023(11) 0.0274(12) 0.0014(12) C17 0.0641(15) 0.0487(14) 0.0599(14) 0.0032(11) 0.0270(12) -0.0011(12) C18 0.0633(15) 0.0468(13) 0.0560(13) 0.0021(11) 0.0262(11) -0.0050(11) C19 0.0648(17) 0.0630(17) 0.0773(18) 0.0136(14) 0.0234(14) 0.0045(13) C20 0.0640(18) 0.092(2) 0.087(2) 0.0123(18) 0.0142(16) -0.0137(17) C21 0.085(2) 0.071(2) 0.087(2) -0.0045(17) 0.0295(18) -0.0296(17) C22 0.094(2) 0.0453(14) 0.093(2) 0.0031(14) 0.0415(19) -0.0033(14) C23 0.0655(16) 0.0534(15) 0.0748(17) 0.0072(13) 0.0288(14) 0.0028(12) C24 0.080(2) 0.074(2) 0.133(4) -0.004(2) 0.007(3) -0.0205(19) F1 0.112(3) 0.156(4) 0.191(4) -0.036(3) 0.059(3) -0.079(3) F1A 0.112(3) 0.156(4) 0.191(4) -0.036(3) 0.059(3) -0.079(3) F2 0.120(3) 0.125(3) 0.143(5) 0.012(4) -0.053(4) -0.047(2) F2A 0.120(3) 0.125(3) 0.143(5) 0.012(4) -0.053(4) -0.047(2) F3 0.123(4) 0.080(2) 0.167(5) -0.030(3) 0.012(3) -0.033(2) F3A 0.123(4) 0.080(2) 0.167(5) -0.030(3) 0.012(3) -0.033(2) O1 0.0779(14) 0.0538(11) 0.0905(14) 0.0109(10) 0.0252(11) 0.0124(10) O2 0.0565(10) 0.0545(10) 0.0703(11) 0.0043(8) 0.0177(8) 0.0036(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 125.1(3) . . ? O1 C1 O2 117.5(3) . . ? O2 C1 C2 117.4(2) . . ? C3 C2 C1 121.3(2) . . ? C3 C2 C16 124.2(2) . . ? C16 C2 C1 114.5(2) . . ? C2 C3 C4 118.8(2) . . ? C2 C3 C10 120.2(2) . . ? C4 C3 C10 120.9(2) . . ? C5 C4 C3 118.6(2) . . ? C5 C4 C9 116.8(2) . . ? C9 C4 C3 124.6(2) . . ? C6 C5 C4 122.4(2) . . ? O2 C5 C4 121.7(2) . . ? O2 C5 C6 115.9(2) . . ? C5 C6 H6 120.4 . . ? C7 C6 C5 119.2(3) . . ? C7 C6 H6 120.4 . . ? C6 C7 C8 120.5(3) . . ? C6 C7 C24 118.8(3) . . ? C8 C7 C24 120.7(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 C7 119.7(3) . . ? C9 C8 H8 120.2 . . ? C4 C9 H9 119.3 . . ? C8 C9 C4 121.4(3) . . ? C8 C9 H9 119.3 . . ? C11 C10 C3 121.1(2) . . ? C11 C10 C15 119.0(2) . . ? C15 C10 C3 119.9(2) . . ? C10 C11 H11 120.0 . . ? C12 C11 C10 120.1(3) . . ? C12 C11 H11 120.0 . . ? C11 C12 H12 119.9 . . ? C13 C12 C11 120.3(3) . . ? C13 C12 H12 119.9 . . ? C12 C13 H13 119.8 . . ? C12 C13 C14 120.3(3) . . ? C14 C13 H13 119.8 . . ? C13 C14 H14 120.0 . . ? C15 C14 C13 119.9(3) . . ? C15 C14 H14 120.0 . . ? C10 C15 H15 119.8 . . ? C14 C15 C10 120.4(3) . . ? C14 C15 H15 119.8 . . ? C17 C16 C2 177.3(3) . . ? C16 C17 C18 178.3(3) . . ? C19 C18 C17 120.5(2) . . ? C19 C18 C23 118.7(3) . . ? C23 C18 C17 120.8(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 C18 120.0(3) . . ? C20 C19 H19 120.0 . . ? C19 C20 H20 119.5 . . ? C21 C20 C19 121.0(3) . . ? C21 C20 H20 119.5 . . ? C20 C21 H21 120.2 . . ? C20 C21 C22 119.5(3) . . ? C22 C21 H21 120.2 . . ? C21 C22 H22 119.8 . . ? C23 C22 C21 120.5(3) . . ? C23 C22 H22 119.8 . . ? C18 C23 H23 119.9 . . ? C22 C23 C18 120.3(3) . . ? C22 C23 H23 119.9 . . ? F1 C24 C7 108.6(4) . . ? F1A C24 C7 107.0(5) . . ? F2 C24 C7 115.0(4) . . ? F2 C24 F1 104.3(5) . . ? F2 C24 F3 113.3(5) . . ? F2A C24 C7 117.9(8) . . ? F2A C24 F1A 98.9(8) . . ? F3 C24 C7 114.8(4) . . ? F3 C24 F1 98.9(5) . . ? F3A C24 C7 119.3(7) . . ? F3A C24 F1A 100.8(7) . . ? F3A C24 F2A 109.3(10) . . ? C1 O2 C5 122.0(2) . . ? 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 C1 C2 1.475(4) . ? C1 O1 1.197(3) . ? C1 O2 1.363(3) . ? C2 C3 1.364(3) . ? C2 C16 1.419(4) . ? C3 C4 1.446(3) . ? C3 C10 1.490(4) . ? C4 C5 1.396(4) . ? C4 C9 1.399(4) . ? C5 C6 1.374(4) . ? C5 O2 1.371(3) . ? C6 H6 0.9300 . ? C6 C7 1.371(4) . ? C7 C8 1.388(4) . ? C7 C24 1.480(4) . ? C8 H8 0.9300 . ? C8 C9 1.374(4) . ? C9 H9 0.9300 . ? C10 C11 1.389(4) . ? C10 C15 1.390(4) . ? C11 H11 0.9300 . ? C11 C12 1.385(4) . ? C12 H12 0.9300 . ? C12 C13 1.364(4) . ? C13 H13 0.9300 . ? C13 C14 1.381(5) . ? C14 H14 0.9300 . ? C14 C15 1.377(4) . ? C15 H15 0.9300 . ? C16 C17 1.201(4) . ? C17 C18 1.427(4) . ? C18 C19 1.387(4) . ? C18 C23 1.390(4) . ? C19 H19 0.9300 . ? C19 C20 1.376(4) . ? C20 H20 0.9300 . ? C20 C21 1.360(5) . ? C21 H21 0.9300 . ? C21 C22 1.375(5) . ? C22 H22 0.9300 . ? C22 C23 1.373(4) . ? C23 H23 0.9300 . ? C24 F1 1.375(6) . ? C24 F1A 1.435(9) . ? C24 F2 1.300(6) . ? C24 F2A 1.263(12) . ? C24 F3 1.337(6) . ? C24 F3A 1.227(9) . ? 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 C1 C2 C3 C4 -0.4(4) . . . . ? C1 C2 C3 C10 179.1(2) . . . . ? C2 C1 O2 C5 -2.3(3) . . . . ? C2 C3 C4 C5 -1.7(3) . . . . ? C2 C3 C4 C9 178.0(2) . . . . ? C2 C3 C10 C11 118.6(3) . . . . ? C2 C3 C10 C15 -59.2(3) . . . . ? C3 C4 C5 C6 -177.7(2) . . . . ? C3 C4 C5 O2 1.9(4) . . . . ? C3 C4 C9 C8 178.0(3) . . . . ? C3 C10 C11 C12 -177.9(2) . . . . ? C3 C10 C15 C14 179.2(3) . . . . ? C4 C3 C10 C11 -61.9(3) . . . . ? C4 C3 C10 C15 120.3(3) . . . . ? C4 C5 C6 C7 -0.8(4) . . . . ? C4 C5 O2 C1 0.2(4) . . . . ? C5 C4 C9 C8 -2.3(4) . . . . ? C5 C6 C7 C8 -1.5(5) . . . . ? C5 C6 C7 C24 179.2(3) . . . . ? C6 C5 O2 C1 179.7(2) . . . . ? C6 C7 C8 C9 1.9(5) . . . . ? C6 C7 C24 F1 82.0(5) . . . . ? C6 C7 C24 F1A -99.5(7) . . . . ? C6 C7 C24 F2 -34.4(7) . . . . ? C6 C7 C24 F2A 10.6(10) . . . . ? C6 C7 C24 F3 -168.4(5) . . . . ? C6 C7 C24 F3A 147.1(9) . . . . ? C7 C8 C9 C4 0.1(5) . . . . ? C8 C7 C24 F1 -97.3(5) . . . . ? C8 C7 C24 F1A 81.2(8) . . . . ? C8 C7 C24 F2 146.3(5) . . . . ? C8 C7 C24 F2A -168.7(9) . . . . ? C8 C7 C24 F3 12.3(7) . . . . ? C8 C7 C24 F3A -32.2(10) . . . . ? C9 C4 C5 C6 2.7(4) . . . . ? C9 C4 C5 O2 -177.8(2) . . . . ? C10 C3 C4 C5 178.8(2) . . . . ? C10 C3 C4 C9 -1.6(4) . . . . ? C10 C11 C12 C13 -1.3(5) . . . . ? C11 C10 C15 C14 1.3(4) . . . . ? C11 C12 C13 C14 1.5(5) . . . . ? C12 C13 C14 C15 -0.3(5) . . . . ? C13 C14 C15 C10 -1.1(5) . . . . ? C15 C10 C11 C12 -0.1(4) . . . . ? C16 C2 C3 C4 178.4(2) . . . . ? C16 C2 C3 C10 -2.1(4) . . . . ? C17 C18 C19 C20 179.8(3) . . . . ? C17 C18 C23 C22 -179.9(3) . . . . ? C18 C19 C20 C21 0.2(5) . . . . ? C19 C18 C23 C22 -0.1(4) . . . . ? C19 C20 C21 C22 -0.2(5) . . . . ? C20 C21 C22 C23 0.0(5) . . . . ? C21 C22 C23 C18 0.1(5) . . . . ? C23 C18 C19 C20 0.0(4) . . . . ? C24 C7 C8 C9 -178.8(4) . . . . ? O1 C1 C2 C3 -178.5(3) . . . . ? O1 C1 C2 C16 2.5(4) . . . . ? O1 C1 O2 C5 178.6(2) . . . . ? O2 C1 C2 C3 2.4(4) . . . . ? O2 C1 C2 C16 -176.5(2) . . . . ? O2 C5 C6 C7 179.6(3) . . . . ?