#------------------------------------------------------------------------------ #$Date: 2020-04-09 06:46:58 +0300 (Thu, 09 Apr 2020) $ #$Revision: 250529 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157454.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_7157454 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_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00479K _journal_year 2020 _chemical_formula_moiety 'C24 H15 F O3' _chemical_formula_sum 'C24 H15 F O3' _chemical_formula_weight 370.36 _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2019-11-15 _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 21.9897(6) _cell_length_b 12.2777(3) _cell_length_c 13.5508(4) _cell_measurement_reflns_used 3453 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 69.4180 _cell_measurement_theta_min 4.0300 _cell_volume 3658.48(17) _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _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 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 -97.00 -49.00 1.00 1.50 -- -33.50 178.00-120.00 48 2 \w -101.00 -51.00 1.00 1.50 -- -33.50 -57.00 -90.00 50 3 \w -45.00 -17.00 1.00 1.50 -- -33.50 -57.00-150.00 28 4 \w 71.00 110.00 1.00 1.50 -- 36.47 178.00-150.00 39 5 \w 41.00 68.00 1.00 1.50 -- 36.47 -99.00 -90.00 27 6 \w 60.00 109.00 1.00 1.50 -- 36.47 178.00 -30.00 49 7 \w -4.00 22.00 1.00 1.50 -- 36.47 -99.00 -90.00 26 8 \w 59.00 106.00 1.00 5.00 -- 108.00-111.00 -60.00 47 9 \w 105.00 178.00 1.00 5.00 -- 108.00 111.00-150.00 73 10 \w 40.00 78.00 1.00 5.00 -- 108.00 -94.00-180.00 38 11 \w 100.00 178.00 1.00 5.00 -- 108.00 111.00 90.00 78 12 \w 47.00 131.00 1.00 5.00 -- 108.00 -30.00 120.00 84 13 \w -102.00 -76.00 1.00 2.50 -- -33.50 178.00-180.00 26 14 \w 47.00 72.00 1.00 2.50 -- 36.47 -19.00 90.00 25 15 \w 31.00 62.00 1.00 2.50 -- 36.47 -99.00 60.00 31 16 \w -32.00 33.00 1.00 2.50 -- 36.47 -19.00 90.00 65 17 \w 45.00 88.00 1.00 2.50 -- 36.47 56.00-117.00 43 18 \w 32.00 58.00 1.00 2.50 -- 36.47 -99.00 -30.00 26 19 \w 59.00 105.00 1.00 3.00 -- 108.00 -94.00 -30.00 46 20 \w 111.00 148.00 1.00 3.00 -- 108.00 61.00 0.00 37 21 \w 125.00 151.00 1.00 3.00 -- 108.00 61.00 60.00 26 22 \w 92.00 104.00 1.00 3.00 -- 108.00 61.00 -60.00 12 ; _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 -0.0024437000 _diffrn_orient_matrix_UB_12 0.0829850000 _diffrn_orient_matrix_UB_13 0.0850143000 _diffrn_orient_matrix_UB_21 0.0690592000 _diffrn_orient_matrix_UB_22 -0.0120387000 _diffrn_orient_matrix_UB_23 0.0146894000 _diffrn_orient_matrix_UB_31 0.0110280000 _diffrn_orient_matrix_UB_32 0.0932896000 _diffrn_orient_matrix_UB_33 -0.0737560000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_unetI/netI 0.0371 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 13127 _diffrn_reflns_point_group_measured_fraction_full 0.750 _diffrn_reflns_point_group_measured_fraction_max 0.750 _diffrn_reflns_theta_full 67.337 _diffrn_reflns_theta_max 67.337 _diffrn_reflns_theta_min 3.600 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.782 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90866 _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 1.345 _exptl_crystal_description block _exptl_crystal_F_000 1536 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.163 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; Flack x determined using 876 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.15(18) _refine_ls_extinction_coef 0.00211(16) _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 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 508 _refine_ls_number_reflns 4929 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0421 _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^)+(0.0545P)^2^+0.0553P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1018 _refine_ls_wR_factor_ref 0.1161 _reflns_Friedel_coverage 0.435 _reflns_Friedel_fraction_full 0.477 _reflns_Friedel_fraction_max 0.477 _reflns_number_gt 3789 _reflns_number_total 4929 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201911292.res created by SHELXL-2014/7 TITL CF solution in Pca21 CELL 1.54184 21.989687 12.277655 13.550821 90 90 90 ZERR 8 0.000567 0.000281 0.000409 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,+Y,0.5+Z SYMM 0.5+X,-Y,+Z SFAC C H F O UNIT 192 120 8 24 L.S. 4 0 0 PLAN 20 SIZE 0.1 0.13 0.16 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 0.054500 0.055300 EXTI 0.002107 FVAR 2.27181 C1 1 0.556682 0.202046 0.620022 11.00000 0.04253 0.05460 = 0.06033 0.00081 0.00711 0.00446 C2 1 0.597137 0.296158 0.628780 11.00000 0.04207 0.05019 = 0.04876 -0.00024 0.00607 0.00387 C3 1 0.658939 0.283638 0.635028 11.00000 0.04273 0.04721 = 0.04265 -0.00021 0.00251 0.00421 C4 1 0.684006 0.174744 0.634196 11.00000 0.04551 0.05126 = 0.04608 -0.00152 0.00090 0.00431 C5 1 0.645314 0.086060 0.623353 11.00000 0.04390 0.05160 = 0.05678 -0.00029 -0.00076 0.00182 C6 1 0.665256 -0.020286 0.622475 11.00000 0.05970 0.04794 = 0.08451 -0.00337 -0.00474 0.00420 AFIX 43 H6 2 0.638475 -0.077991 0.613102 11.00000 -1.20000 AFIX 0 C7 1 0.726219 -0.037352 0.636002 11.00000 0.06247 0.04842 = 0.08041 -0.00059 -0.00520 0.01687 C8 1 0.767299 0.045211 0.648642 11.00000 0.04713 0.06268 = 0.07859 -0.00471 -0.00497 0.01132 AFIX 43 H8 2 0.808402 0.030429 0.657680 11.00000 -1.20000 AFIX 0 C9 1 0.746040 0.151233 0.647613 11.00000 0.04607 0.05547 = 0.06384 -0.00482 -0.00572 0.00084 AFIX 43 H9 2 0.773395 0.208259 0.655985 11.00000 -1.20000 AFIX 0 C10 1 0.699338 0.380373 0.642127 11.00000 0.04747 0.04580 = 0.06290 -0.00300 -0.01124 0.00519 C11 1 0.743630 0.399586 0.571271 11.00000 0.04764 0.06325 = 0.07716 0.00592 -0.00443 -0.00060 AFIX 43 H11 2 0.749316 0.349987 0.520226 11.00000 -1.20000 AFIX 0 C12 1 0.779262 0.491904 0.576196 11.00000 0.05055 0.07590 = 0.12031 0.02191 -0.01130 -0.00796 AFIX 43 H12 2 0.808248 0.505263 0.527708 11.00000 -1.20000 AFIX 0 C13 1 0.771912 0.564263 0.652897 11.00000 0.07477 0.05880 = 0.16438 0.00451 -0.04162 -0.01170 AFIX 43 H13 2 0.796321 0.625974 0.656764 11.00000 -1.20000 AFIX 0 C14 1 0.728958 0.545427 0.722940 11.00000 0.09274 0.06576 = 0.12943 -0.03329 -0.03634 0.01190 AFIX 43 H14 2 0.724044 0.594872 0.774317 11.00000 -1.20000 AFIX 0 C15 1 0.692571 0.454145 0.718976 11.00000 0.06871 0.06576 = 0.08082 -0.01928 -0.01630 0.01236 AFIX 43 H15 2 0.663551 0.441996 0.767671 11.00000 -1.20000 AFIX 0 C16 1 0.567322 0.399107 0.628145 11.00000 0.04264 0.05782 = 0.04751 0.00129 0.00232 0.00295 C17 1 0.540313 0.483726 0.628970 11.00000 0.04941 0.05502 = 0.05071 0.00240 0.00157 0.00766 C18 1 0.509590 0.586235 0.631059 11.00000 0.04768 0.05689 = 0.04355 -0.00274 0.00283 0.00805 C19 1 0.540673 0.682914 0.640625 11.00000 0.03972 0.06169 = 0.07437 -0.00538 -0.00135 0.00446 AFIX 43 H19 2 0.582796 0.681847 0.646680 11.00000 -1.20000 AFIX 0 C20 1 0.510357 0.781825 0.641400 11.00000 0.05148 0.05272 = 0.07951 -0.00549 0.00241 -0.00338 AFIX 43 H20 2 0.532204 0.846380 0.647076 11.00000 -1.20000 AFIX 0 C21 1 0.447687 0.784740 0.633750 11.00000 0.04806 0.04742 = 0.05065 -0.00176 0.00456 0.00524 C22 1 0.416061 0.688252 0.624001 11.00000 0.03983 0.05649 = 0.05183 -0.00247 0.00111 0.00077 AFIX 43 H22 2 0.373922 0.689892 0.618348 11.00000 -1.20000 AFIX 0 C23 1 0.445846 0.589521 0.622498 11.00000 0.04957 0.04352 = 0.04855 -0.00166 0.00082 0.00092 AFIX 43 H23 2 0.423872 0.525219 0.615841 11.00000 -1.20000 AFIX 0 C24 1 0.444454 0.978298 0.636461 11.00000 0.07956 0.04604 = 0.11408 -0.00586 0.00006 -0.00008 AFIX 137 H24A 2 0.464735 0.986182 0.698788 11.00000 -1.50000 H24B 2 0.415765 1.036517 0.628157 11.00000 -1.50000 H24C 2 0.473872 0.980709 0.584161 11.00000 -1.50000 AFIX 0 F1 3 0.746941 -0.141468 0.636609 11.00000 0.08227 0.05423 = 0.14757 -0.00629 -0.01586 0.02256 O1 4 0.502113 0.204985 0.615903 11.00000 0.04048 0.06751 = 0.10486 0.00467 0.00491 0.00001 O2 4 0.583427 0.100985 0.614089 11.00000 0.04258 0.05146 = 0.08432 0.00075 -0.00299 0.00067 O3 4 0.413359 0.876892 0.633908 11.00000 0.05552 0.04710 = 0.08747 -0.00407 0.00176 0.00651 C1' 1 0.455336 0.428307 0.390154 11.00000 0.04679 0.05172 = 0.05813 -0.00435 0.00009 0.00600 C2' 1 0.495524 0.521549 0.378323 11.00000 0.04241 0.04990 = 0.04465 -0.00148 -0.00502 0.00421 C3' 1 0.557205 0.509502 0.372465 11.00000 0.04821 0.04452 = 0.03884 -0.00027 -0.00095 0.00404 C4' 1 0.582290 0.400281 0.372184 11.00000 0.04607 0.05121 = 0.03985 0.00363 -0.00298 0.00805 C5' 1 0.543467 0.312147 0.383221 11.00000 0.04658 0.05193 = 0.04798 0.00096 -0.00244 0.00610 C6' 1 0.563768 0.205006 0.382919 11.00000 0.06446 0.04650 = 0.06089 -0.00079 -0.00405 0.00562 AFIX 43 H6' 2 0.537033 0.147098 0.391587 11.00000 -1.20000 AFIX 0 C7' 1 0.624574 0.188186 0.369376 11.00000 0.06648 0.05241 = 0.05927 -0.00233 -0.00959 0.01852 C8' 1 0.665313 0.271010 0.356149 11.00000 0.05362 0.06380 = 0.05997 -0.00504 -0.00468 0.01645 AFIX 43 H8' 2 0.706357 0.256302 0.346325 11.00000 -1.20000 AFIX 0 C9' 1 0.644302 0.376787 0.357671 11.00000 0.04759 0.06154 = 0.05239 -0.00092 -0.00095 0.00430 AFIX 43 H9' 2 0.671647 0.433762 0.348935 11.00000 -1.20000 AFIX 0 C10' 1 0.597389 0.605618 0.366719 11.00000 0.04699 0.04685 = 0.05583 -0.00007 0.00522 0.00502 C11' 1 0.641513 0.622752 0.439083 11.00000 0.05089 0.05896 = 0.06205 -0.00246 -0.00241 -0.00187 AFIX 43 H11' 2 0.647108 0.571590 0.488871 11.00000 -1.20000 AFIX 0 C12' 1 0.677012 0.716046 0.436762 11.00000 0.05778 0.07175 = 0.10311 -0.01403 -0.00818 -0.00896 AFIX 43 H12' 2 0.705914 0.727805 0.485721 11.00000 -1.20000 AFIX 0 C13' 1 0.669811 0.790746 0.363075 11.00000 0.06720 0.05699 = 0.15479 0.00558 0.00798 -0.00996 AFIX 43 H13' 2 0.693684 0.853263 0.362158 11.00000 -1.20000 AFIX 0 C14' 1 0.627175 0.773712 0.289911 11.00000 0.07131 0.06096 = 0.13279 0.03542 0.00968 0.00358 AFIX 43 H14' 2 0.622759 0.824286 0.239324 11.00000 -1.20000 AFIX 0 C15' 1 0.590880 0.681223 0.291719 11.00000 0.05974 0.06145 = 0.07622 0.01434 0.00428 0.00732 AFIX 43 H15' 2 0.562128 0.670046 0.242418 11.00000 -1.20000 AFIX 0 C16' 1 0.465858 0.624672 0.377147 11.00000 0.04346 0.05717 = 0.05001 -0.00060 -0.00338 0.00521 C17' 1 0.439455 0.710163 0.377448 11.00000 0.05128 0.05294 = 0.04802 -0.00083 0.00058 0.00610 C18' 1 0.408007 0.812183 0.379489 11.00000 0.04945 0.04707 = 0.04622 -0.00121 0.00112 0.00957 C19' 1 0.438829 0.909174 0.370174 11.00000 0.04239 0.06019 = 0.08966 0.00317 0.00823 0.00530 AFIX 43 H19' 2 0.480643 0.908599 0.359897 11.00000 -1.20000 AFIX 0 C20' 1 0.408337 1.007554 0.375919 11.00000 0.05093 0.05073 = 0.12106 0.00669 0.00976 -0.00543 AFIX 43 H20' 2 0.429682 1.072560 0.369484 11.00000 -1.20000 AFIX 0 C21' 1 0.346240 1.009348 0.391198 11.00000 0.05027 0.04459 = 0.08104 0.00095 -0.00126 0.00668 C22' 1 0.315147 0.912973 0.399236 11.00000 0.04254 0.05142 = 0.07985 -0.00258 0.00373 0.00521 AFIX 43 H22' 2 0.273264 0.913763 0.408742 11.00000 -1.20000 AFIX 0 C23' 1 0.345308 0.815373 0.393372 11.00000 0.04729 0.04611 = 0.06695 -0.00324 0.00023 -0.00133 AFIX 43 H23' 2 0.323622 0.750612 0.398732 11.00000 -1.20000 AFIX 0 C24' 1 0.343226 1.203687 0.399898 11.00000 0.09177 0.04337 = 0.23829 0.00300 0.01683 0.00760 AFIX 137 H24D 2 0.374269 1.203845 0.449710 11.00000 -1.50000 H24E 2 0.314647 1.260981 0.413064 11.00000 -1.50000 H24F 2 0.361458 1.215077 0.336360 11.00000 -1.50000 AFIX 0 F1' 3 0.644820 0.083855 0.368208 11.00000 0.09147 0.05511 = 0.10216 -0.00383 -0.00586 0.02712 O1' 4 0.400882 0.431422 0.399310 11.00000 0.04516 0.06345 = 0.11454 0.00171 0.00592 0.00398 O2' 4 0.481729 0.326313 0.393972 11.00000 0.04637 0.04872 = 0.07511 0.00167 -0.00083 0.00304 O3' 4 0.312463 1.101362 0.400730 11.00000 0.06121 0.04593 = 0.17510 -0.00139 0.01023 0.01108 HKLF 4 REM CF solution in Pca21 REM R1 = 0.0421 for 3789 Fo > 4sig(Fo) and 0.0573 for all 4929 data REM 508 parameters refined using 1 restraints END WGHT 0.0545 0.0553 REM Highest difference peak 0.163, deepest hole -0.150, 1-sigma level 0.035 Q1 1 0.5156 0.4040 0.6358 11.00000 0.05 0.16 Q2 1 0.6265 0.2879 0.6032 11.00000 0.05 0.16 Q3 1 0.5222 0.5138 0.4052 11.00000 0.05 0.15 Q4 1 0.4206 0.6271 0.3945 11.00000 0.05 0.15 Q5 1 0.4918 0.5840 0.6368 11.00000 0.05 0.15 Q6 1 0.5689 0.3618 0.4165 11.00000 0.05 0.14 Q7 1 0.7824 0.2366 0.6575 11.00000 0.05 0.14 Q8 1 0.5864 0.2804 0.6384 11.00000 0.05 0.14 Q9 1 0.4788 0.7808 0.6501 11.00000 0.05 0.14 Q10 1 0.5680 0.4642 0.3939 11.00000 0.05 0.14 Q11 1 0.3871 1.2107 0.3807 11.00000 0.05 0.13 Q12 1 0.5613 0.4826 0.3805 11.00000 0.05 0.13 Q13 1 0.3781 0.8167 0.4128 11.00000 0.05 0.13 Q14 1 0.5814 0.4808 0.6367 11.00000 0.05 0.13 Q15 1 0.3868 0.5313 0.3978 11.00000 0.05 0.13 Q16 1 0.5933 0.2075 0.3954 11.00000 0.05 0.12 Q17 1 0.4126 0.4925 0.6196 11.00000 0.05 0.12 Q18 1 0.4919 0.9831 0.6625 11.00000 0.05 0.12 Q19 1 0.6256 -0.0102 0.3641 11.00000 0.05 0.12 Q20 1 0.7155 0.1601 0.6227 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0421 for 3789 Fo > 4sig(Fo) and 0.0573 for all 13801 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.16, deepest hole -0.15 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0573 REM R1_gt = 0.0421 REM wR_ref = 0.1161 REM GOOF = 1.021 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 13801 REM Reflections_gt = 3789 REM Parameters = n/a REM Hole = -0.15 REM Peak = 0.16 REM Flack = -0.15(18) ; _cod_data_source_file d0ob00479k2.cif _cod_data_source_block 201911292 _cod_original_cell_volume 3658.47(17) _cod_database_code 7157454 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C40H40O2N4F1 _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 0.926 _shelx_estimated_absorpt_t_min 0.885 _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.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), C22(H22), C23(H23), C6'(H6'), C8'(H8'), C9'(H9'), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C19'(H19'), C20'(H20'), C22'(H22'), C23'(H23') 2.b Idealised Me refined as rotating group: C24(H24A,H24B,H24C), C24'(H24D,H24E,H24F) ; _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 1.297 _oxdiff_exptl_absorpt_empirical_full_min 0.932 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -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 C1 C 0.55668(16) 0.2020(3) 0.6200(3) 0.0525(9) Uani 1 1 d . . . . . C2 C 0.59714(16) 0.2962(3) 0.6288(3) 0.0470(8) Uani 1 1 d . . . . . C3 C 0.65894(15) 0.2836(3) 0.6350(3) 0.0442(8) Uani 1 1 d . . . . . C4 C 0.68401(16) 0.1747(3) 0.6342(3) 0.0476(8) Uani 1 1 d . . . . . C5 C 0.64531(16) 0.0861(3) 0.6234(3) 0.0508(9) Uani 1 1 d . . . . . C6 C 0.66526(19) -0.0203(3) 0.6225(3) 0.0641(11) Uani 1 1 d . . . . . H6 H 0.6385 -0.0780 0.6131 0.077 Uiso 1 1 calc R . . . . C7 C 0.72622(19) -0.0374(3) 0.6360(4) 0.0638(11) Uani 1 1 d . . . . . C8 C 0.76730(18) 0.0452(3) 0.6486(4) 0.0628(11) Uani 1 1 d . . . . . H8 H 0.8084 0.0304 0.6577 0.075 Uiso 1 1 calc R . . . . C9 C 0.74604(18) 0.1512(3) 0.6476(3) 0.0551(9) Uani 1 1 d . . . . . H9 H 0.7734 0.2083 0.6560 0.066 Uiso 1 1 calc R . . . . C10 C 0.69934(16) 0.3804(3) 0.6421(3) 0.0521(9) Uani 1 1 d . . . . . C11 C 0.74363(18) 0.3996(3) 0.5713(4) 0.0627(11) Uani 1 1 d . . . . . H11 H 0.7493 0.3500 0.5202 0.075 Uiso 1 1 calc R . . . . C12 C 0.7793(2) 0.4919(4) 0.5762(5) 0.0823(15) Uani 1 1 d . . . . . H12 H 0.8082 0.5053 0.5277 0.099 Uiso 1 1 calc R . . . . C13 C 0.7719(3) 0.5643(4) 0.6529(6) 0.099(2) Uani 1 1 d . . . . . H13 H 0.7963 0.6260 0.6568 0.119 Uiso 1 1 calc R . . . . C14 C 0.7290(3) 0.5454(4) 0.7229(5) 0.0960(19) Uani 1 1 d . . . . . H14 H 0.7240 0.5949 0.7743 0.115 Uiso 1 1 calc R . . . . C15 C 0.6926(2) 0.4541(4) 0.7190(4) 0.0718(12) Uani 1 1 d . . . . . H15 H 0.6636 0.4420 0.7677 0.086 Uiso 1 1 calc R . . . . C16 C 0.56732(16) 0.3991(3) 0.6281(3) 0.0493(8) Uani 1 1 d . . . . . C17 C 0.54031(17) 0.4837(3) 0.6290(3) 0.0517(9) Uani 1 1 d . . . . . C18 C 0.50959(16) 0.5862(3) 0.6311(3) 0.0494(8) Uani 1 1 d . . . . . C19 C 0.54067(17) 0.6829(3) 0.6406(3) 0.0586(10) Uani 1 1 d . . . . . H19 H 0.5828 0.6818 0.6467 0.070 Uiso 1 1 calc R . . . . C20 C 0.51036(18) 0.7818(3) 0.6414(4) 0.0612(10) Uani 1 1 d . . . . . H20 H 0.5322 0.8464 0.6471 0.073 Uiso 1 1 calc R . . . . C21 C 0.44769(17) 0.7847(3) 0.6338(3) 0.0487(8) Uani 1 1 d . . . . . C22 C 0.41606(16) 0.6883(3) 0.6240(3) 0.0494(8) Uani 1 1 d . . . . . H22 H 0.3739 0.6899 0.6183 0.059 Uiso 1 1 calc R . . . . C23 C 0.44585(17) 0.5895(3) 0.6225(3) 0.0472(8) Uani 1 1 d . . . . . H23 H 0.4239 0.5252 0.6158 0.057 Uiso 1 1 calc R . . . . C24 C 0.4445(2) 0.9783(3) 0.6365(4) 0.0799(14) Uani 1 1 d . . . . . H24A H 0.4647 0.9862 0.6988 0.120 Uiso 1 1 calc GR . . . . H24B H 0.4158 1.0365 0.6282 0.120 Uiso 1 1 calc GR . . . . H24C H 0.4739 0.9807 0.5842 0.120 Uiso 1 1 calc GR . . . . F1 F 0.74694(14) -0.14147(17) 0.6366(3) 0.0947(9) Uani 1 1 d . . . . . O1 O 0.50211(12) 0.2050(2) 0.6159(3) 0.0709(9) Uani 1 1 d . . . . . O2 O 0.58343(11) 0.1010(2) 0.6141(2) 0.0595(8) Uani 1 1 d . . . . . O3 O 0.41336(12) 0.8769(2) 0.6339(3) 0.0634(7) Uani 1 1 d . . . . . C1' C 0.45534(17) 0.4283(3) 0.3902(3) 0.0522(9) Uani 1 1 d . . . . . C2' C 0.49552(15) 0.5215(3) 0.3783(3) 0.0457(8) Uani 1 1 d . . . . . C3' C 0.55721(15) 0.5095(3) 0.3725(3) 0.0439(7) Uani 1 1 d . . . . . C4' C 0.58229(16) 0.4003(3) 0.3722(3) 0.0457(8) Uani 1 1 d . . . . . C5' C 0.54347(16) 0.3121(3) 0.3832(3) 0.0488(8) Uani 1 1 d . . . . . C6' C 0.56377(19) 0.2050(3) 0.3829(3) 0.0573(10) Uani 1 1 d . . . . . H6' H 0.5370 0.1471 0.3916 0.069 Uiso 1 1 calc R . . . . C7' C 0.6246(2) 0.1882(3) 0.3694(3) 0.0594(10) Uani 1 1 d . . . . . C8' C 0.66531(19) 0.2710(3) 0.3561(3) 0.0591(10) Uani 1 1 d . . . . . H8' H 0.7064 0.2563 0.3463 0.071 Uiso 1 1 calc R . . . . C9' C 0.64430(17) 0.3768(3) 0.3577(3) 0.0538(9) Uani 1 1 d . . . . . H9' H 0.6716 0.4338 0.3489 0.065 Uiso 1 1 calc R . . . . C10' C 0.59739(16) 0.6056(3) 0.3667(3) 0.0499(9) Uani 1 1 d . . . . . C11' C 0.64151(18) 0.6228(3) 0.4391(3) 0.0573(10) Uani 1 1 d . . . . . H11' H 0.6471 0.5716 0.4889 0.069 Uiso 1 1 calc R . . . . C12' C 0.6770(2) 0.7160(4) 0.4368(4) 0.0775(14) Uani 1 1 d . . . . . H12' H 0.7059 0.7278 0.4857 0.093 Uiso 1 1 calc R . . . . C13' C 0.6698(2) 0.7907(4) 0.3631(6) 0.0930(18) Uani 1 1 d . . . . . H13' H 0.6937 0.8533 0.3622 0.112 Uiso 1 1 calc R . . . . C14' C 0.6272(2) 0.7737(4) 0.2899(5) 0.0884(17) Uani 1 1 d . . . . . H14' H 0.6228 0.8243 0.2393 0.106 Uiso 1 1 calc R . . . . C15' C 0.5909(2) 0.6812(3) 0.2917(3) 0.0658(11) Uani 1 1 d . . . . . H15' H 0.5621 0.6700 0.2424 0.079 Uiso 1 1 calc R . . . . C16' C 0.46586(16) 0.6247(3) 0.3771(3) 0.0502(8) Uani 1 1 d . . . . . C17' C 0.43945(17) 0.7102(3) 0.3774(3) 0.0507(8) Uani 1 1 d . . . . . C18' C 0.40801(16) 0.8122(3) 0.3795(3) 0.0476(8) Uani 1 1 d . . . . . C19' C 0.43883(17) 0.9092(3) 0.3702(4) 0.0641(11) Uani 1 1 d . . . . . H19' H 0.4806 0.9086 0.3599 0.077 Uiso 1 1 calc R . . . . C20' C 0.40834(18) 1.0076(3) 0.3759(5) 0.0742(13) Uani 1 1 d . . . . . H20' H 0.4297 1.0726 0.3695 0.089 Uiso 1 1 calc R . . . . C21' C 0.34624(17) 1.0093(3) 0.3912(3) 0.0586(10) Uani 1 1 d . . . . . C22' C 0.31515(17) 0.9130(3) 0.3992(3) 0.0579(10) Uani 1 1 d . . . . . H22' H 0.2733 0.9138 0.4087 0.070 Uiso 1 1 calc R . . . . C23' C 0.34531(16) 0.8154(3) 0.3934(3) 0.0535(10) Uani 1 1 d . . . . . H23' H 0.3236 0.7506 0.3987 0.064 Uiso 1 1 calc R . . . . C24' C 0.3432(3) 1.2037(3) 0.3999(6) 0.124(3) Uani 1 1 d . . . . . H24D H 0.3743 1.2038 0.4497 0.187 Uiso 1 1 calc GR . . . . H24E H 0.3146 1.2610 0.4131 0.187 Uiso 1 1 calc GR . . . . H24F H 0.3615 1.2151 0.3364 0.187 Uiso 1 1 calc GR . . . . F1' F 0.64482(13) 0.08385(18) 0.3682(2) 0.0829(8) Uani 1 1 d . . . . . O1' O 0.40088(13) 0.4314(2) 0.3993(3) 0.0744(10) Uani 1 1 d . . . . . O2' O 0.48173(11) 0.32631(19) 0.3940(2) 0.0567(7) Uani 1 1 d . . . . . O3' O 0.31246(14) 1.1014(2) 0.4007(3) 0.0941(13) 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 0.0425(18) 0.055(2) 0.060(2) 0.0008(19) 0.0071(19) 0.0045(17) C2 0.0421(17) 0.0502(18) 0.0488(19) -0.0002(17) 0.0061(19) 0.0039(15) C3 0.0427(17) 0.0472(18) 0.0426(17) -0.0002(16) 0.0025(17) 0.0042(14) C4 0.0455(18) 0.0513(19) 0.0461(19) -0.0015(17) 0.0009(18) 0.0043(15) C5 0.0439(19) 0.052(2) 0.057(2) -0.0003(18) -0.001(2) 0.0018(16) C6 0.060(2) 0.048(2) 0.085(3) -0.003(2) -0.005(2) 0.0042(18) C7 0.062(2) 0.048(2) 0.080(3) -0.001(2) -0.005(3) 0.0169(18) C8 0.047(2) 0.063(2) 0.079(3) -0.005(2) -0.005(2) 0.0113(18) C9 0.0461(18) 0.055(2) 0.064(3) -0.005(2) -0.0057(19) 0.0008(18) C10 0.047(2) 0.0458(18) 0.063(2) -0.0030(19) -0.011(2) 0.0052(15) C11 0.048(2) 0.063(2) 0.077(3) 0.006(2) -0.004(2) -0.0006(19) C12 0.051(2) 0.076(3) 0.120(4) 0.022(3) -0.011(3) -0.008(2) C13 0.075(3) 0.059(3) 0.164(7) 0.005(4) -0.042(4) -0.012(3) C14 0.093(4) 0.066(3) 0.129(5) -0.033(3) -0.036(4) 0.012(3) C15 0.069(3) 0.066(3) 0.081(3) -0.019(2) -0.016(2) 0.012(2) C16 0.0426(18) 0.058(2) 0.0475(19) 0.0013(18) 0.0023(19) 0.0029(17) C17 0.0494(19) 0.055(2) 0.051(2) 0.0024(19) 0.0016(19) 0.0077(17) C18 0.0477(19) 0.057(2) 0.0435(19) -0.0027(18) 0.0028(19) 0.0080(16) C19 0.0397(18) 0.062(2) 0.074(3) -0.005(2) -0.001(2) 0.0045(17) C20 0.051(2) 0.053(2) 0.080(3) -0.005(2) 0.002(2) -0.0034(18) C21 0.0481(18) 0.0474(19) 0.051(2) -0.0018(18) 0.005(2) 0.0052(16) C22 0.0398(17) 0.056(2) 0.052(2) -0.0025(18) 0.0011(18) 0.0008(16) C23 0.0496(19) 0.0435(18) 0.049(2) -0.0017(17) 0.0008(18) 0.0009(15) C24 0.080(3) 0.046(2) 0.114(4) -0.006(3) 0.000(3) 0.000(2) F1 0.0823(17) 0.0542(12) 0.148(3) -0.0063(18) -0.0159(19) 0.0226(14) O1 0.0405(13) 0.0675(18) 0.105(3) 0.0047(18) 0.0049(17) 0.0000(13) O2 0.0426(13) 0.0515(14) 0.084(2) 0.0007(14) -0.0030(14) 0.0007(12) O3 0.0555(15) 0.0471(14) 0.087(2) -0.0041(15) 0.0018(16) 0.0065(12) C1' 0.047(2) 0.052(2) 0.058(2) -0.0043(19) 0.0001(19) 0.0060(16) C2' 0.0424(17) 0.0499(19) 0.0447(19) -0.0015(17) -0.0050(17) 0.0042(15) C3' 0.0482(18) 0.0445(17) 0.0388(17) -0.0003(17) -0.0009(17) 0.0040(15) C4' 0.0461(18) 0.0512(18) 0.0398(17) 0.0036(18) -0.0030(17) 0.0080(15) C5' 0.0466(19) 0.0519(19) 0.048(2) 0.0010(19) -0.0024(19) 0.0061(15) C6' 0.064(2) 0.0465(19) 0.061(2) -0.0008(19) -0.004(2) 0.0056(18) C7' 0.066(3) 0.052(2) 0.059(2) -0.002(2) -0.010(2) 0.0185(19) C8' 0.054(2) 0.064(2) 0.060(3) -0.005(2) -0.005(2) 0.016(2) C9' 0.0476(19) 0.062(2) 0.052(2) -0.0009(19) -0.0009(18) 0.0043(17) C10' 0.047(2) 0.0468(18) 0.056(2) -0.0001(19) 0.0052(19) 0.0050(15) C11' 0.051(2) 0.059(2) 0.062(2) -0.002(2) -0.0024(19) -0.0019(18) C12' 0.058(3) 0.072(3) 0.103(4) -0.014(3) -0.008(3) -0.009(2) C13' 0.067(3) 0.057(3) 0.155(6) 0.006(4) 0.008(4) -0.010(2) C14' 0.071(3) 0.061(3) 0.133(5) 0.035(3) 0.010(3) 0.004(2) C15' 0.060(2) 0.061(2) 0.076(3) 0.014(2) 0.004(2) 0.007(2) C16' 0.0435(18) 0.057(2) 0.050(2) -0.0006(19) -0.0034(18) 0.0052(17) C17' 0.051(2) 0.053(2) 0.048(2) -0.0008(19) 0.0006(19) 0.0061(17) C18' 0.0494(19) 0.0471(18) 0.0462(19) -0.0012(18) 0.0011(19) 0.0096(15) C19' 0.0424(19) 0.060(2) 0.090(3) 0.003(2) 0.008(2) 0.0053(17) C20' 0.051(2) 0.051(2) 0.121(4) 0.007(3) 0.010(3) -0.0054(18) C21' 0.050(2) 0.0446(19) 0.081(3) 0.001(2) -0.001(2) 0.0067(16) C22' 0.0425(18) 0.051(2) 0.080(3) -0.003(2) 0.004(2) 0.0052(16) C23' 0.047(2) 0.0461(19) 0.067(3) -0.0032(19) 0.000(2) -0.0013(16) C24' 0.092(4) 0.043(2) 0.238(9) 0.003(4) 0.017(5) 0.008(2) F1' 0.0915(18) 0.0551(13) 0.102(2) -0.0038(14) -0.0059(18) 0.0271(12) O1' 0.0452(15) 0.0634(16) 0.115(3) 0.0017(18) 0.0059(17) 0.0040(13) O2' 0.0464(14) 0.0487(13) 0.0751(19) 0.0017(14) -0.0008(14) 0.0030(11) O3' 0.0612(18) 0.0459(14) 0.175(4) -0.001(2) 0.010(2) 0.0111(13) 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 126.0(4) . . ? O1 C1 O2 116.8(4) . . ? O2 C1 C2 117.2(3) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 C16 123.8(3) . . ? C16 C2 C1 114.9(3) . . ? C2 C3 C4 118.8(3) . . ? C2 C3 C10 120.5(3) . . ? C4 C3 C10 120.8(3) . . ? C5 C4 C3 119.5(3) . . ? C5 C4 C9 116.5(3) . . ? C9 C4 C3 124.0(3) . . ? C6 C5 C4 123.3(3) . . ? C6 C5 O2 116.1(3) . . ? O2 C5 C4 120.6(3) . . ? C5 C6 H6 121.4 . . ? C7 C6 C5 117.1(4) . . ? C7 C6 H6 121.4 . . ? C8 C7 C6 123.3(3) . . ? F1 C7 C6 118.3(4) . . ? F1 C7 C8 118.4(4) . . ? C7 C8 H8 120.9 . . ? C7 C8 C9 118.2(4) . . ? C9 C8 H8 120.9 . . ? C4 C9 H9 119.3 . . ? C8 C9 C4 121.5(4) . . ? C8 C9 H9 119.3 . . ? C11 C10 C3 120.7(4) . . ? C11 C10 C15 118.9(4) . . ? C15 C10 C3 120.4(4) . . ? C10 C11 H11 119.8 . . ? C12 C11 C10 120.3(5) . . ? C12 C11 H11 119.8 . . ? C11 C12 H12 120.0 . . ? C13 C12 C11 120.0(5) . . ? C13 C12 H12 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 C12 119.9(5) . . ? C14 C13 H13 120.0 . . ? C13 C14 H14 119.5 . . ? C13 C14 C15 121.0(5) . . ? C15 C14 H14 119.5 . . ? C10 C15 H15 120.1 . . ? C14 C15 C10 119.8(5) . . ? C14 C15 H15 120.1 . . ? C17 C16 C2 177.5(4) . . ? C16 C17 C18 178.4(4) . . ? C19 C18 C17 121.8(3) . . ? C19 C18 C23 118.5(3) . . ? C23 C18 C17 119.6(3) . . ? C18 C19 H19 119.4 . . ? C18 C19 C20 121.2(4) . . ? C20 C19 H19 119.4 . . ? C19 C20 H20 119.9 . . ? C21 C20 C19 120.1(4) . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 119.2(3) . . ? O3 C21 C20 125.1(3) . . ? O3 C21 C22 115.8(3) . . ? C21 C22 H22 119.4 . . ? C23 C22 C21 121.1(3) . . ? C23 C22 H22 119.4 . . ? C18 C23 H23 120.1 . . ? C22 C23 C18 119.8(3) . . ? C22 C23 H23 120.1 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O3 C24 H24A 109.5 . . ? O3 C24 H24B 109.5 . . ? O3 C24 H24C 109.5 . . ? C1 O2 C5 122.4(3) . . ? C21 O3 C24 117.5(3) . . ? O1' C1' C2' 126.2(3) . . ? O1' C1' O2' 116.3(3) . . ? O2' C1' C2' 117.5(3) . . ? C3' C2' C1' 121.6(3) . . ? C3' C2' C16' 123.4(3) . . ? C16' C2' C1' 115.0(3) . . ? C2' C3' C4' 118.5(3) . . ? C2' C3' C10' 120.7(3) . . ? C4' C3' C10' 120.8(3) . . ? C5' C4' C3' 119.2(3) . . ? C5' C4' C9' 116.9(3) . . ? C9' C4' C3' 123.9(3) . . ? C4' C5' C6' 122.7(3) . . ? O2' C5' C4' 121.3(3) . . ? O2' C5' C6' 115.9(3) . . ? C5' C6' H6' 121.4 . . ? C7' C6' C5' 117.3(4) . . ? C7' C6' H6' 121.4 . . ? C6' C7' C8' 123.2(3) . . ? F1' C7' C6' 117.8(4) . . ? F1' C7' C8' 119.1(4) . . ? C7' C8' H8' 120.7 . . ? C7' C8' C9' 118.6(4) . . ? C9' C8' H8' 120.7 . . ? C4' C9' H9' 119.3 . . ? C8' C9' C4' 121.3(4) . . ? C8' C9' H9' 119.3 . . ? C11' C10' C3' 120.0(4) . . ? C15' C10' C3' 120.9(4) . . ? C15' C10' C11' 119.1(4) . . ? C10' C11' H11' 120.0 . . ? C12' C11' C10' 120.0(4) . . ? C12' C11' H11' 120.0 . . ? C11' C12' H12' 119.8 . . ? C13' C12' C11' 120.4(5) . . ? C13' C12' H12' 119.8 . . ? C12' C13' H13' 119.9 . . ? C12' C13' C14' 120.2(5) . . ? C14' C13' H13' 119.9 . . ? C13' C14' H14' 119.9 . . ? C13' C14' C15' 120.1(5) . . ? C15' C14' H14' 119.9 . . ? C10' C15' C14' 120.1(5) . . ? C10' C15' H15' 119.9 . . ? C14' C15' H15' 119.9 . . ? C17' C16' C2' 178.1(4) . . ? C16' C17' C18' 179.1(5) . . ? C19' C18' C17' 121.2(3) . . ? C19' C18' C23' 118.4(3) . . ? C23' C18' C17' 120.4(3) . . ? C18' C19' H19' 119.6 . . ? C18' C19' C20' 120.8(4) . . ? C20' C19' H19' 119.6 . . ? C19' C20' H20' 120.0 . . ? C21' C20' C19' 120.1(4) . . ? C21' C20' H20' 120.0 . . ? C22' C21' C20' 119.4(3) . . ? O3' C21' C20' 124.6(4) . . ? O3' C21' C22' 116.0(3) . . ? C21' C22' H22' 119.7 . . ? C21' C22' C23' 120.5(4) . . ? C23' C22' H22' 119.7 . . ? C18' C23' H23' 119.6 . . ? C22' C23' C18' 120.7(3) . . ? C22' C23' H23' 119.6 . . ? H24D C24' H24E 109.5 . . ? H24D C24' H24F 109.5 . . ? H24E C24' H24F 109.5 . . ? O3' C24' H24D 109.5 . . ? O3' C24' H24E 109.5 . . ? O3' C24' H24F 109.5 . . ? C5' O2' C1' 121.7(3) . . ? C21' O3' C24' 118.2(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 C1 C2 1.463(5) . ? C1 O1 1.202(4) . ? C1 O2 1.375(4) . ? C2 C3 1.370(5) . ? C2 C16 1.424(5) . ? C3 C4 1.446(5) . ? C3 C10 1.486(5) . ? C4 C5 1.390(5) . ? C4 C9 1.406(5) . ? C5 C6 1.377(5) . ? C5 O2 1.379(4) . ? C6 H6 0.9300 . ? C6 C7 1.369(6) . ? C7 C8 1.369(5) . ? C7 F1 1.357(4) . ? C8 H8 0.9300 . ? C8 C9 1.383(5) . ? C9 H9 0.9300 . ? C10 C11 1.388(6) . ? C10 C15 1.388(6) . ? C11 H11 0.9300 . ? C11 C12 1.380(6) . ? C12 H12 0.9300 . ? C12 C13 1.377(9) . ? C13 H13 0.9300 . ? C13 C14 1.359(9) . ? C14 H14 0.9300 . ? C14 C15 1.378(7) . ? C15 H15 0.9300 . ? C16 C17 1.197(5) . ? C17 C18 1.429(5) . ? C18 C19 1.376(5) . ? C18 C23 1.407(5) . ? C19 H19 0.9300 . ? C19 C20 1.385(5) . ? C20 H20 0.9300 . ? C20 C21 1.382(5) . ? C21 C22 1.380(5) . ? C21 O3 1.360(4) . ? C22 H22 0.9300 . ? C22 C23 1.378(5) . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C24 O3 1.421(5) . ? C1' C2' 1.455(5) . ? C1' O1' 1.204(4) . ? C1' O2' 1.381(4) . ? C2' C3' 1.367(4) . ? C2' C16' 1.424(4) . ? C3' C4' 1.450(4) . ? C3' C10' 1.476(5) . ? C4' C5' 1.386(5) . ? C4' C9' 1.408(5) . ? C5' C6' 1.389(4) . ? C5' O2' 1.376(4) . ? C6' H6' 0.9300 . ? C6' C7' 1.365(6) . ? C7' C8' 1.367(6) . ? C7' F1' 1.356(4) . ? C8' H8' 0.9300 . ? C8' C9' 1.379(5) . ? C9' H9' 0.9300 . ? C10' C11' 1.395(5) . ? C10' C15' 1.384(5) . ? C11' H11' 0.9300 . ? C11' C12' 1.386(6) . ? C12' H12' 0.9300 . ? C12' C13' 1.365(8) . ? C13' H13' 0.9300 . ? C13' C14' 1.380(8) . ? C14' H14' 0.9300 . ? C14' C15' 1.388(6) . ? C15' H15' 0.9300 . ? C16' C17' 1.200(5) . ? C17' C18' 1.431(4) . ? C18' C19' 1.376(5) . ? C18' C23' 1.392(5) . ? C19' H19' 0.9300 . ? C19' C20' 1.384(5) . ? C20' H20' 0.9300 . ? C20' C21' 1.381(5) . ? C21' C22' 1.371(5) . ? C21' O3' 1.358(4) . ? C22' H22' 0.9300 . ? C22' C23' 1.372(5) . ? C23' H23' 0.9300 . ? C24' H24D 0.9600 . ? C24' H24E 0.9600 . ? C24' H24F 0.9600 . ? C24' O3' 1.427(5) . ? 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 -0.8(6) . . . . ? C1 C2 C3 C10 178.9(4) . . . . ? C2 C1 O2 C5 4.8(6) . . . . ? C2 C3 C4 C5 2.4(6) . . . . ? C2 C3 C4 C9 -175.0(4) . . . . ? C2 C3 C10 C11 -120.4(4) . . . . ? C2 C3 C10 C15 58.4(5) . . . . ? C3 C4 C5 C6 -179.5(4) . . . . ? C3 C4 C5 O2 -0.4(6) . . . . ? C3 C4 C9 C8 178.3(4) . . . . ? C3 C10 C11 C12 177.3(4) . . . . ? C3 C10 C15 C14 -177.8(4) . . . . ? C4 C3 C10 C11 59.3(5) . . . . ? C4 C3 C10 C15 -121.9(4) . . . . ? C4 C5 C6 C7 2.0(7) . . . . ? C4 C5 O2 C1 -3.4(6) . . . . ? C5 C4 C9 C8 0.8(6) . . . . ? C5 C6 C7 C8 -1.0(8) . . . . ? C5 C6 C7 F1 179.2(4) . . . . ? C6 C5 O2 C1 175.8(4) . . . . ? C6 C7 C8 C9 0.0(8) . . . . ? C7 C8 C9 C4 0.1(7) . . . . ? C9 C4 C5 C6 -1.9(6) . . . . ? C9 C4 C5 O2 177.2(4) . . . . ? C10 C3 C4 C5 -177.3(4) . . . . ? C10 C3 C4 C9 5.2(6) . . . . ? C10 C11 C12 C13 1.5(7) . . . . ? C11 C10 C15 C14 1.0(6) . . . . ? C11 C12 C13 C14 -0.9(8) . . . . ? C12 C13 C14 C15 0.4(9) . . . . ? C13 C14 C15 C10 -0.5(8) . . . . ? C15 C10 C11 C12 -1.5(6) . . . . ? C16 C2 C3 C4 -179.5(4) . . . . ? C16 C2 C3 C10 0.3(6) . . . . ? C17 C18 C19 C20 179.2(4) . . . . ? C17 C18 C23 C22 -179.7(4) . . . . ? C18 C19 C20 C21 0.8(7) . . . . ? C19 C18 C23 C22 -0.1(6) . . . . ? C19 C20 C21 C22 -0.9(7) . . . . ? C19 C20 C21 O3 179.9(4) . . . . ? C20 C21 C22 C23 0.5(7) . . . . ? C20 C21 O3 C24 3.8(7) . . . . ? C21 C22 C23 C18 0.0(6) . . . . ? C22 C21 O3 C24 -175.5(4) . . . . ? C23 C18 C19 C20 -0.3(7) . . . . ? F1 C7 C8 C9 179.8(4) . . . . ? O1 C1 C2 C3 178.6(4) . . . . ? O1 C1 C2 C16 -2.6(7) . . . . ? O1 C1 O2 C5 -176.3(4) . . . . ? O2 C1 C2 C3 -2.7(6) . . . . ? O2 C1 C2 C16 176.1(3) . . . . ? O2 C5 C6 C7 -177.2(4) . . . . ? O3 C21 C22 C23 179.8(3) . . . . ? C1' C2' C3' C4' 3.7(6) . . . . ? C1' C2' C3' C10' -176.2(4) . . . . ? C2' C1' O2' C5' -2.5(6) . . . . ? C2' C3' C4' C5' -3.5(6) . . . . ? C2' C3' C4' C9' 174.1(4) . . . . ? C2' C3' C10' C11' 120.5(4) . . . . ? C2' C3' C10' C15' -57.7(5) . . . . ? C3' C4' C5' C6' 179.4(4) . . . . ? C3' C4' C5' O2' 0.3(6) . . . . ? C3' C4' C9' C8' -178.6(4) . . . . ? C3' C10' C11' C12' -176.4(4) . . . . ? C3' C10' C15' C14' 177.0(4) . . . . ? C4' C3' C10' C11' -59.4(5) . . . . ? C4' C3' C10' C15' 122.4(4) . . . . ? C4' C5' C6' C7' -1.1(7) . . . . ? C4' C5' O2' C1' 2.7(6) . . . . ? C5' C4' C9' C8' -1.0(6) . . . . ? C5' C6' C7' C8' -0.2(7) . . . . ? C5' C6' C7' F1' -179.5(4) . . . . ? C6' C5' O2' C1' -176.5(4) . . . . ? C6' C7' C8' C9' 0.8(7) . . . . ? C7' C8' C9' C4' -0.2(6) . . . . ? C9' C4' C5' C6' 1.7(6) . . . . ? C9' C4' C5' O2' -177.5(4) . . . . ? C10' C3' C4' C5' 176.4(4) . . . . ? C10' C3' C4' C9' -6.0(6) . . . . ? C10' C11' C12' C13' -1.1(7) . . . . ? C11' C10' C15' C14' -1.1(6) . . . . ? C11' C12' C13' C14' -0.2(8) . . . . ? C12' C13' C14' C15' 0.9(9) . . . . ? C13' C14' C15' C10' -0.2(8) . . . . ? C15' C10' C11' C12' 1.8(6) . . . . ? C16' C2' C3' C4' -178.7(4) . . . . ? C16' C2' C3' C10' 1.4(6) . . . . ? C17' C18' C19' C20' -177.6(5) . . . . ? C17' C18' C23' C22' 177.5(4) . . . . ? C18' C19' C20' C21' 0.0(9) . . . . ? C19' C18' C23' C22' -1.1(7) . . . . ? C19' C20' C21' C22' -0.9(9) . . . . ? C19' C20' C21' O3' 178.0(5) . . . . ? C20' C21' C22' C23' 0.8(8) . . . . ? C20' C21' O3' C24' -3.3(9) . . . . ? C21' C22' C23' C18' 0.2(7) . . . . ? C22' C21' O3' C24' 175.7(5) . . . . ? C23' C18' C19' C20' 0.9(7) . . . . ? F1' C7' C8' C9' -179.9(4) . . . . ? O1' C1' C2' C3' 177.3(4) . . . . ? O1' C1' C2' C16' -0.5(7) . . . . ? O1' C1' O2' C5' 179.2(4) . . . . ? O2' C1' C2' C3' -0.9(6) . . . . ? O2' C1' C2' C16' -178.6(3) . . . . ? O2' C5' C6' C7' 178.1(4) . . . . ? O3' C21' C22' C23' -178.2(4) . . . . ?