#------------------------------------------------------------------------------ #$Date: 2024-04-25 01:28:41 +0300 (Thu, 25 Apr 2024) $ #$Revision: 291347 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/14/1571482.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_1571482 loop_ _publ_author_name 'Conboy, A\'ife' 'Goodfellow, Alister S.' 'Kasten, Kevin' 'Dunne, Joanne' 'Cordes, David Bradford' 'Buehl, Michael' 'Smith, Andrew D.' _publ_section_title ; De-epimerizing DyKAT of \b-Lactones Generated by Isothiourea-Catalysed Enantioselective [2+2] Cycloaddition ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC01410C _journal_year 2024 _chemical_absolute_configuration ad _chemical_formula_moiety 'C22 H22 Cl N3 O4, C H Cl3' _chemical_formula_sum 'C23 H23 Cl4 N3 O4' _chemical_formula_weight 547.24 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_block_doi 10.5517/ccdc.csd.cc2hp63j _audit_creation_date 2023-12-13 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2023-12-13 deposited with the CCDC. 2024-04-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.043(2) _cell_length_b 10.783(3) _cell_length_c 28.473(8) _cell_measurement_reflns_used 4274 _cell_measurement_temperature 173 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.4 _cell_volume 2469.4(12) _computing_cell_refinement ; CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015) ; _computing_data_collection 'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)' _computing_data_reduction ; CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015) ; _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 173 _diffrn_detector 'hybrid photon counting detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_detector_type 'Dectris PILATUS P200K' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; scan: Number of images: 324 Slice: -112.0000 - 50.0000 Image width: 0.5000 Exp time: 5.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 160.0000 XTD: 50.0488 2theta: -22.1712 scan: Number of images: 346 Slice: -109.0000 - 64.0000 Image width: 0.5000 Exp time: 5.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: -20.0000 XTD: 50.0488 2theta: -22.1712 scan: Number of images: 168 Slice: -88.0000 - -4.0000 Image width: 0.5000 Exp time: 5.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 305.0000 XTD: 50.0488 2theta: -22.1712 scan: Number of images: 90 Slice: -102.0000 - -57.0000 Image width: 0.5000 Exp time: 5.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 16.0000 XTD: 50.0488 2theta: -22.1712 scan: Number of images: 360 Slice: -112.0000 - 68.0000 Image width: 0.5000 Exp time: 5.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 52.0000 XTD: 50.0488 2theta: -22.1712 scan: Number of images: 248 Slice: -79.5000 - 44.5000 Image width: 0.5000 Exp time: 5.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 88.0000 XTD: 50.0488 2theta: -22.1712 ; _diffrn_measurement_device 'AFC10: Fixed \c 3 circle' _diffrn_measurement_device_type 'Rigaku XtaLAB P200K' _diffrn_measurement_method 'shutterless scans' _diffrn_measurement_specimen_support Loop _diffrn_orient_matrix_type d*Trek _diffrn_orient_matrix_UB_11 0.053152 _diffrn_orient_matrix_UB_12 -0.040637 _diffrn_orient_matrix_UB_13 -0.104798 _diffrn_orient_matrix_UB_21 -0.037052 _diffrn_orient_matrix_UB_22 0.071232 _diffrn_orient_matrix_UB_23 -0.046414 _diffrn_orient_matrix_UB_31 0.028481 _diffrn_orient_matrix_UB_32 0.019340 _diffrn_orient_matrix_UB_33 0.006946 _diffrn_radiation_monochromator 'Rigaku Osmic Confocal Optical System' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_unetI/netI 0.0317 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 32369 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.338 _diffrn_reflns_theta_min 2.369 _diffrn_source 'Rotating Anode' _diffrn_source_current 66.0 _diffrn_source_power 3.0 _diffrn_source_type 'Rigaku FR-X' _diffrn_source_voltage 45.0 _exptl_absorpt_coefficient_mu 0.515 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.588 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.472 _exptl_crystal_description Prism _exptl_crystal_F_000 1128 _exptl_crystal_preparation Loop _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Chloroform/hexane/ethyl acetate' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.480 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.065 _refine_ls_abs_structure_details ; Flack x determined using 1530 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.02(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 312 _refine_ls_number_reflns 4495 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0462 _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^)+(0.0871P)^2^+1.3115P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1321 _refine_ls_wR_factor_ref 0.1390 _reflns_Friedel_coverage 0.739 _reflns_Friedel_fraction_full 0.996 _reflns_Friedel_fraction_max 0.996 _reflns_number_gt 3977 _reflns_number_total 4495 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc01410c2.cif _cod_data_source_block 21 _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_cell_volume 2469.3(11) _cod_original_sg_symbol_H-M P212121 _cod_database_code 1571482 _shelx_shelxl_version_number 2019/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances O1-H1 0.98 with sigma of 0.02 3.a Ternary CH refined with riding coordinates: C6(H6), C31(H31) 3.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B) 3.c Aromatic/amide H refined with riding coordinates: C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25) 3.d Idealised Me refined as rotating group: C26(H26A,H26B,H26C) ; _shelx_res_file ; TITL acas1_a.res in P2(1)2(1)2(1) acas1.res created by SHELXL-2019/3 at 22:47:53 on 13-Dec-2023 REM Old TITL REM SHELXT solution in P2(1)2(1)2(1): R1 0.140, Rweak 0.029, Alpha 0.004 REM 1.077 for 25 systematic absences, Orientation as input REM Flack x = 0.072 ( 0.031 ) from 1708 Parsons' quotients REM Formula found by SHELXT: C23 Cl4 N3 O4 CELL 0.71073 8.0428 10.7826 28.4733 90 90 90 ZERR 4 0.0021 0.0029 0.0078 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H Cl N O UNIT 92 92 16 12 16 EQIV $1 1-X,0.5+Y,1.5-Z DFIX 0.98 O1 H1 L.S. 4 PLAN 5 TEMP -100 CONF HTAB O1 O7_$1 list 4 MORE -1 BOND $H fmap 2 acta OMIT 0 1 1 OMIT 2 0 1 REM REM REM WGHT 0.087100 1.311500 FVAR 0.41489 CL1 3 0.801812 0.699894 0.495502 11.00000 0.04731 0.07624 = 0.02768 0.00594 0.01483 0.01064 CL31 3 0.894623 0.072413 0.509700 11.00000 0.09610 0.06455 = 0.07204 -0.01498 -0.00497 -0.01488 CL32 3 0.719248 0.219974 0.578363 11.00000 0.07561 0.10128 = 0.07864 -0.00359 0.00769 -0.00622 CL33 3 0.817690 0.326424 0.489791 11.00000 0.11860 0.09851 = 0.09306 0.02809 0.01289 0.03351 O1 5 0.569244 0.890315 0.706935 11.00000 0.04747 0.02825 = 0.02281 -0.00315 0.00480 -0.01297 H1 2 0.577047 0.942395 0.733481 11.00000 0.05585 O2 5 0.790794 0.663301 0.705443 11.00000 0.02413 0.06811 = 0.02846 -0.00462 0.00738 0.00730 O7 5 0.401153 0.529671 0.717016 11.00000 0.04171 0.02846 = 0.03040 0.00744 -0.00824 -0.00396 O11 5 0.038050 0.437917 0.592031 11.00000 0.04582 0.03527 = 0.04400 -0.00380 -0.01265 -0.00495 N3 4 0.664803 0.666444 0.778408 11.00000 0.01963 0.03342 = 0.02160 -0.00301 0.00128 0.00463 N4 4 0.513933 0.709345 0.798092 11.00000 0.02239 0.03018 = 0.02574 -0.00150 0.00362 0.00206 N8 4 0.193931 0.568972 0.665903 11.00000 0.02228 0.02768 = 0.02823 0.00505 0.00084 -0.00410 C1 1 0.521709 0.767628 0.719075 11.00000 0.02478 0.02400 = 0.02173 -0.00213 0.00520 -0.00343 C2 1 0.676060 0.690887 0.731223 11.00000 0.02289 0.03350 = 0.02349 -0.00535 -0.00007 -0.00354 C5 1 0.431893 0.764015 0.766188 11.00000 0.02629 0.02503 = 0.02245 0.00046 0.00438 0.00174 C6 1 0.417719 0.722467 0.677081 11.00000 0.02130 0.02252 = 0.02088 -0.00060 -0.00025 0.00263 AFIX 13 H6 2 0.327312 0.784576 0.671779 11.00000 -1.20000 AFIX 0 C7 1 0.334841 0.598313 0.688196 11.00000 0.02398 0.02554 = 0.02143 -0.00008 0.00281 0.00065 C9 1 0.117059 0.635158 0.626457 11.00000 0.02398 0.02787 = 0.03484 0.00393 -0.00621 -0.00020 AFIX 23 H9A 2 0.178811 0.712860 0.620227 11.00000 -1.20000 H9B 2 0.000944 0.657094 0.634466 11.00000 -1.20000 AFIX 0 C10 1 0.119289 0.554815 0.583557 11.00000 0.03475 0.04102 = 0.02967 0.00625 -0.00448 0.00073 AFIX 23 H10A 2 0.062482 0.598374 0.557493 11.00000 -1.20000 H10B 2 0.235863 0.539669 0.573978 11.00000 -1.20000 AFIX 0 C12 1 0.117463 0.373249 0.629318 11.00000 0.03451 0.03250 = 0.04606 0.00114 -0.00522 -0.00210 AFIX 23 H12A 2 0.234498 0.356181 0.620700 11.00000 -1.20000 H12B 2 0.060971 0.292796 0.634423 11.00000 -1.20000 AFIX 0 C13 1 0.112635 0.448159 0.674067 11.00000 0.03537 0.02883 = 0.03985 0.00728 -0.00010 -0.01160 AFIX 23 H13A 2 -0.004113 0.461185 0.683918 11.00000 -1.20000 H13B 2 0.171073 0.402902 0.699418 11.00000 -1.20000 AFIX 0 C14 1 0.518686 0.713900 0.631913 11.00000 0.01824 0.03062 = 0.01838 0.00117 -0.00265 -0.00233 C15 1 0.549684 0.821683 0.606498 11.00000 0.02678 0.02997 = 0.02388 -0.00214 -0.00268 0.00005 AFIX 43 H15 2 0.509028 0.898804 0.617828 11.00000 -1.20000 AFIX 0 C16 1 0.639229 0.818130 0.564796 11.00000 0.02419 0.03910 = 0.02577 0.00814 -0.00166 -0.00308 AFIX 43 H16 2 0.660892 0.892058 0.547708 11.00000 -1.20000 AFIX 0 C17 1 0.695921 0.705488 0.548726 11.00000 0.02215 0.05630 = 0.02004 -0.00044 0.00088 -0.00036 C18 1 0.668126 0.597139 0.573277 11.00000 0.03065 0.03999 = 0.02832 -0.00408 0.00672 0.00782 AFIX 43 H18 2 0.708526 0.520119 0.561776 11.00000 -1.20000 AFIX 0 C19 1 0.579294 0.602999 0.615425 11.00000 0.03329 0.02845 = 0.02416 0.00222 0.00067 0.00121 AFIX 43 H19 2 0.560575 0.529271 0.632909 11.00000 -1.20000 AFIX 0 C20 1 0.776669 0.601094 0.808387 11.00000 0.02510 0.02569 = 0.03216 -0.00731 -0.00986 0.00295 C21 1 0.934830 0.570786 0.792613 11.00000 0.02627 0.05877 = 0.03641 -0.01359 -0.00601 0.00664 AFIX 43 H21 2 0.969919 0.593031 0.761888 11.00000 -1.20000 AFIX 0 C22 1 1.041014 0.507037 0.822811 11.00000 0.02952 0.07005 = 0.06442 -0.01669 -0.01008 0.02050 AFIX 43 H22 2 1.148773 0.484425 0.812164 11.00000 -1.20000 AFIX 0 C23 1 0.993279 0.476108 0.867705 11.00000 0.04243 0.04756 = 0.05761 -0.00402 -0.02134 0.01334 AFIX 43 H23 2 1.066848 0.432528 0.887929 11.00000 -1.20000 AFIX 0 C24 1 0.834637 0.509973 0.882999 11.00000 0.04383 0.03980 = 0.04412 0.00520 -0.01224 -0.00223 AFIX 43 H24 2 0.800020 0.489940 0.913983 11.00000 -1.20000 AFIX 0 C25 1 0.728179 0.572277 0.853359 11.00000 0.03037 0.03038 = 0.03235 0.00423 -0.00757 -0.00067 AFIX 43 H25 2 0.620695 0.595446 0.864056 11.00000 -1.20000 AFIX 0 C26 1 0.268240 0.822934 0.775689 11.00000 0.03024 0.04211 = 0.02798 0.00409 0.00561 0.01058 AFIX 137 H26A 2 0.235800 0.807001 0.808312 11.00000 -1.50000 H26B 2 0.184392 0.788072 0.754490 11.00000 -1.50000 H26C 2 0.276626 0.912576 0.770528 11.00000 -1.50000 AFIX 0 C31 1 0.867859 0.221548 0.533832 11.00000 0.06755 0.07141 = 0.05302 -0.00876 -0.00894 -0.01387 AFIX 13 H31 2 0.976174 0.247774 0.547929 11.00000 -1.20000 AFIX 0 HKLF 4 REM acas1_a.res in P2(1)2(1)2(1) REM wR2 = 0.1390, GooF = S = 1.031, Restrained GooF = 1.032 for all data REM R1 = 0.0462 for 3977 Fo > 4sig(Fo) and 0.0533 for all 4495 data REM 312 parameters refined using 1 restraints END WGHT 0.0871 1.3115 REM Highest difference peak 0.480, deepest hole -0.456, 1-sigma level 0.065 Q1 1 0.6754 0.3029 0.4935 11.00000 0.05 0.48 Q2 1 0.7588 0.2362 0.5080 11.00000 0.05 0.27 Q3 1 0.4775 0.7343 0.6960 11.00000 0.05 0.26 Q4 1 0.9018 0.3567 0.4555 11.00000 0.05 0.26 Q5 1 0.8171 0.6216 0.4981 11.00000 0.05 0.24 ; _shelx_res_checksum 22392 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.80181(16) 0.69989(14) 0.49550(4) 0.0504(4) Uani 1 1 d . . . . . Cl31 Cl 0.8946(3) 0.07241(16) 0.50970(7) 0.0776(5) Uani 1 1 d . . . . . Cl32 Cl 0.7192(3) 0.2200(2) 0.57836(7) 0.0852(6) Uani 1 1 d . . . . . Cl33 Cl 0.8177(3) 0.3264(2) 0.48979(9) 0.1034(8) Uani 1 1 d . . . . . O1 O 0.5692(4) 0.8903(3) 0.70694(11) 0.0328(7) Uani 1 1 d D . . . . H1 H 0.577(8) 0.942(5) 0.7335(15) 0.056(17) Uiso 1 1 d D . . . . O2 O 0.7908(4) 0.6633(3) 0.70544(11) 0.0402(8) Uani 1 1 d . . . . . O7 O 0.4012(4) 0.5297(3) 0.71702(11) 0.0335(7) Uani 1 1 d . . . . . O11 O 0.0381(4) 0.4379(3) 0.59203(12) 0.0417(8) Uani 1 1 d . . . . . N3 N 0.6648(4) 0.6664(3) 0.77841(11) 0.0249(7) Uani 1 1 d . . . . . N4 N 0.5139(4) 0.7093(3) 0.79809(12) 0.0261(7) Uani 1 1 d . . . . . N8 N 0.1939(4) 0.5690(3) 0.66590(12) 0.0261(7) Uani 1 1 d . . . . . C1 C 0.5217(5) 0.7676(3) 0.71908(14) 0.0235(8) Uani 1 1 d . . . . . C2 C 0.6761(5) 0.6909(4) 0.73122(14) 0.0266(8) Uani 1 1 d . . . . . C5 C 0.4319(5) 0.7640(3) 0.76619(14) 0.0246(8) Uani 1 1 d . . . . . C6 C 0.4177(5) 0.7225(3) 0.67708(13) 0.0216(8) Uani 1 1 d . . . . . H6 H 0.327312 0.784576 0.671779 0.026 Uiso 1 1 calc R U . . . C7 C 0.3348(5) 0.5983(3) 0.68820(14) 0.0236(8) Uani 1 1 d . . . . . C9 C 0.1171(5) 0.6352(4) 0.62646(16) 0.0289(9) Uani 1 1 d . . . . . H9A H 0.178811 0.712860 0.620227 0.035 Uiso 1 1 calc R U . . . H9B H 0.000944 0.657094 0.634466 0.035 Uiso 1 1 calc R U . . . C10 C 0.1193(6) 0.5548(4) 0.58356(16) 0.0351(10) Uani 1 1 d . . . . . H10A H 0.062482 0.598374 0.557493 0.042 Uiso 1 1 calc R U . . . H10B H 0.235863 0.539669 0.573978 0.042 Uiso 1 1 calc R U . . . C12 C 0.1175(6) 0.3732(4) 0.62932(18) 0.0377(11) Uani 1 1 d . . . . . H12A H 0.234498 0.356181 0.620700 0.045 Uiso 1 1 calc R U . . . H12B H 0.060971 0.292796 0.634423 0.045 Uiso 1 1 calc R U . . . C13 C 0.1126(6) 0.4482(4) 0.67407(17) 0.0347(10) Uani 1 1 d . . . . . H13A H -0.004113 0.461185 0.683918 0.042 Uiso 1 1 calc R U . . . H13B H 0.171073 0.402902 0.699418 0.042 Uiso 1 1 calc R U . . . C14 C 0.5187(5) 0.7139(4) 0.63191(13) 0.0224(8) Uani 1 1 d . . . . . C15 C 0.5497(5) 0.8217(4) 0.60650(14) 0.0269(9) Uani 1 1 d . . . . . H15 H 0.509028 0.898804 0.617828 0.032 Uiso 1 1 calc R U . . . C16 C 0.6392(5) 0.8181(4) 0.56480(15) 0.0297(9) Uani 1 1 d . . . . . H16 H 0.660892 0.892058 0.547708 0.036 Uiso 1 1 calc R U . . . C17 C 0.6959(5) 0.7055(5) 0.54873(14) 0.0328(10) Uani 1 1 d . . . . . C18 C 0.6681(6) 0.5971(4) 0.57328(16) 0.0330(10) Uani 1 1 d . . . . . H18 H 0.708526 0.520119 0.561776 0.040 Uiso 1 1 calc R U . . . C19 C 0.5793(5) 0.6030(4) 0.61542(15) 0.0286(9) Uani 1 1 d . . . . . H19 H 0.560575 0.529271 0.632909 0.034 Uiso 1 1 calc R U . . . C20 C 0.7767(5) 0.6011(4) 0.80839(15) 0.0276(9) Uani 1 1 d . . . . . C21 C 0.9348(5) 0.5708(5) 0.79261(18) 0.0405(11) Uani 1 1 d . . . . . H21 H 0.969919 0.593031 0.761888 0.049 Uiso 1 1 calc R U . . . C22 C 1.0410(6) 0.5070(6) 0.8228(2) 0.0547(15) Uani 1 1 d . . . . . H22 H 1.148773 0.484425 0.812164 0.066 Uiso 1 1 calc R U . . . C23 C 0.9933(7) 0.4761(5) 0.8677(2) 0.0492(14) Uani 1 1 d . . . . . H23 H 1.066848 0.432528 0.887929 0.059 Uiso 1 1 calc R U . . . C24 C 0.8346(7) 0.5100(4) 0.88300(19) 0.0426(12) Uani 1 1 d . . . . . H24 H 0.800020 0.489940 0.913983 0.051 Uiso 1 1 calc R U . . . C25 C 0.7282(5) 0.5723(4) 0.85336(15) 0.0310(9) Uani 1 1 d . . . . . H25 H 0.620695 0.595446 0.864056 0.037 Uiso 1 1 calc R U . . . C26 C 0.2682(5) 0.8229(4) 0.77569(16) 0.0334(10) Uani 1 1 d . . . . . H26A H 0.235800 0.807001 0.808312 0.050 Uiso 1 1 calc R U . . . H26B H 0.184392 0.788072 0.754490 0.050 Uiso 1 1 calc R U . . . H26C H 0.276626 0.912576 0.770528 0.050 Uiso 1 1 calc R U . . . C31 C 0.8679(9) 0.2215(6) 0.5338(2) 0.0640(17) Uani 1 1 d . . . . . H31 H 0.976174 0.247774 0.547929 0.077 Uiso 1 1 calc R U . . . 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 Cl1 0.0473(7) 0.0762(9) 0.0277(6) 0.0059(6) 0.0148(5) 0.0106(6) Cl31 0.0961(13) 0.0645(9) 0.0720(11) -0.0150(8) -0.0050(10) -0.0149(9) Cl32 0.0756(12) 0.1013(14) 0.0786(13) -0.0036(11) 0.0077(10) -0.0062(11) Cl33 0.1186(18) 0.0985(15) 0.0931(15) 0.0281(12) 0.0129(14) 0.0335(14) O1 0.0475(18) 0.0282(14) 0.0228(16) -0.0031(12) 0.0048(14) -0.0130(13) O2 0.0241(15) 0.068(2) 0.0285(16) -0.0046(15) 0.0074(13) 0.0073(15) O7 0.0417(16) 0.0285(14) 0.0304(16) 0.0074(13) -0.0082(14) -0.0040(13) O11 0.0458(19) 0.0353(15) 0.0440(19) -0.0038(15) -0.0126(16) -0.0050(15) N3 0.0196(16) 0.0334(17) 0.0216(17) -0.0030(14) 0.0013(13) 0.0046(14) N4 0.0224(16) 0.0302(16) 0.0257(18) -0.0015(15) 0.0036(14) 0.0021(14) N8 0.0223(15) 0.0277(16) 0.0282(17) 0.0050(14) 0.0008(14) -0.0041(14) C1 0.0248(19) 0.0240(18) 0.022(2) -0.0021(15) 0.0052(16) -0.0034(16) C2 0.0229(19) 0.033(2) 0.0235(19) -0.0054(17) -0.0001(16) -0.0035(17) C5 0.0263(19) 0.0250(18) 0.022(2) 0.0005(16) 0.0044(16) 0.0017(15) C6 0.0213(17) 0.0225(17) 0.0209(19) -0.0006(15) -0.0002(15) 0.0026(15) C7 0.0240(19) 0.0255(19) 0.0214(19) -0.0001(16) 0.0028(16) 0.0006(15) C9 0.024(2) 0.0279(19) 0.035(2) 0.0039(17) -0.0062(18) -0.0002(16) C10 0.035(2) 0.041(2) 0.030(2) 0.0063(19) -0.0045(19) 0.001(2) C12 0.035(2) 0.032(2) 0.046(3) 0.001(2) -0.005(2) -0.0021(19) C13 0.035(2) 0.029(2) 0.040(3) 0.0073(19) 0.000(2) -0.0116(19) C14 0.0182(17) 0.0306(19) 0.0184(18) 0.0012(16) -0.0026(14) -0.0023(16) C15 0.027(2) 0.0300(19) 0.024(2) -0.0021(17) -0.0027(16) 0.0001(16) C16 0.024(2) 0.039(2) 0.026(2) 0.0081(18) -0.0017(17) -0.0031(17) C17 0.0222(19) 0.056(3) 0.0200(19) -0.0004(19) 0.0009(16) 0.000(2) C18 0.031(2) 0.040(2) 0.028(2) -0.0041(19) 0.0067(18) 0.0078(19) C19 0.033(2) 0.0285(19) 0.024(2) 0.0022(17) 0.0007(18) 0.0012(17) C20 0.025(2) 0.026(2) 0.032(2) -0.0073(17) -0.0099(17) 0.0029(16) C21 0.026(2) 0.059(3) 0.036(3) -0.014(2) -0.0060(19) 0.007(2) C22 0.030(2) 0.070(3) 0.064(4) -0.017(3) -0.010(2) 0.020(3) C23 0.042(3) 0.048(3) 0.058(4) -0.004(2) -0.021(3) 0.013(2) C24 0.044(3) 0.040(2) 0.044(3) 0.005(2) -0.012(2) -0.002(2) C25 0.030(2) 0.030(2) 0.032(2) 0.0042(19) -0.0076(18) -0.0007(18) C26 0.030(2) 0.042(2) 0.028(2) 0.0041(19) 0.0056(18) 0.0106(19) C31 0.068(4) 0.071(4) 0.053(3) -0.009(3) -0.009(3) -0.014(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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _citation_id _citation_doi _citation_year 1 10.26434/chemrxiv-2024-5l0dx 2024 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 C1 O1 H1 112(4) . . ? C12 O11 C10 110.5(3) . . ? N4 N3 C20 117.7(3) . . ? C2 N3 N4 112.4(3) . . ? C2 N3 C20 129.7(3) . . ? C5 N4 N3 108.3(3) . . ? C7 N8 C9 127.3(3) . . ? C7 N8 C13 120.6(4) . . ? C9 N8 C13 111.3(3) . . ? O1 C1 C2 109.9(3) . . ? O1 C1 C5 111.5(3) . . ? O1 C1 C6 104.6(3) . . ? C2 C1 C6 116.4(3) . . ? C5 C1 C2 99.9(3) . . ? C5 C1 C6 114.7(3) . . ? O2 C2 N3 126.5(4) . . ? O2 C2 C1 127.7(4) . . ? N3 C2 C1 105.7(3) . . ? N4 C5 C1 113.3(3) . . ? N4 C5 C26 121.9(4) . . ? C26 C5 C1 124.7(4) . . ? C1 C6 H6 107.5 . . ? C7 C6 C1 110.7(3) . . ? C7 C6 H6 107.5 . . ? C14 C6 C1 112.7(3) . . ? C14 C6 H6 107.5 . . ? C14 C6 C7 110.7(3) . . ? O7 C7 N8 122.9(4) . . ? O7 C7 C6 118.5(4) . . ? N8 C7 C6 118.6(3) . . ? N8 C9 H9A 109.7 . . ? N8 C9 H9B 109.7 . . ? N8 C9 C10 109.8(3) . . ? H9A C9 H9B 108.2 . . ? C10 C9 H9A 109.7 . . ? C10 C9 H9B 109.7 . . ? O11 C10 C9 111.4(4) . . ? O11 C10 H10A 109.4 . . ? O11 C10 H10B 109.4 . . ? C9 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O11 C12 H12A 109.5 . . ? O11 C12 H12B 109.5 . . ? O11 C12 C13 110.9(4) . . ? H12A C12 H12B 108.1 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? N8 C13 C12 109.1(4) . . ? N8 C13 H13A 109.9 . . ? N8 C13 H13B 109.9 . . ? C12 C13 H13A 109.9 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C15 C14 C6 118.9(3) . . ? C19 C14 C6 122.0(4) . . ? C19 C14 C15 119.1(4) . . ? C14 C15 H15 119.5 . . ? C16 C15 C14 121.0(4) . . ? C16 C15 H15 119.5 . . ? C15 C16 H16 120.6 . . ? C17 C16 C15 118.7(4) . . ? C17 C16 H16 120.6 . . ? C16 C17 Cl1 118.9(4) . . ? C16 C17 C18 121.7(4) . . ? C18 C17 Cl1 119.4(4) . . ? C17 C18 H18 120.7 . . ? C17 C18 C19 118.6(4) . . ? C19 C18 H18 120.7 . . ? C14 C19 C18 120.9(4) . . ? C14 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C21 C20 N3 120.0(4) . . ? C25 C20 N3 119.4(4) . . ? C25 C20 C21 120.6(4) . . ? C20 C21 H21 120.7 . . ? C20 C21 C22 118.6(5) . . ? C22 C21 H21 120.7 . . ? C21 C22 H22 119.3 . . ? C23 C22 C21 121.5(5) . . ? C23 C22 H22 119.3 . . ? C22 C23 H23 120.6 . . ? C22 C23 C24 118.8(5) . . ? C24 C23 H23 120.6 . . ? C23 C24 H24 119.9 . . ? C25 C24 C23 120.3(5) . . ? C25 C24 H24 119.9 . . ? C20 C25 C24 120.3(4) . . ? C20 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C5 C26 H26A 109.5 . . ? C5 C26 H26B 109.5 . . ? C5 C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? Cl31 C31 H31 108.0 . . ? Cl32 C31 Cl31 111.0(4) . . ? Cl32 C31 H31 108.0 . . ? Cl33 C31 Cl31 109.9(3) . . ? Cl33 C31 Cl32 111.9(4) . . ? Cl33 C31 H31 108.0 . . ? 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 Cl1 C17 1.739(4) . ? Cl31 C31 1.762(7) . ? Cl32 C31 1.743(7) . ? Cl33 C31 1.736(7) . ? O1 H1 0.94(3) . ? O1 C1 1.420(5) . ? O2 C2 1.216(5) . ? O7 C7 1.227(5) . ? O11 C10 1.440(6) . ? O11 C12 1.422(6) . ? N3 N4 1.414(5) . ? N3 C2 1.372(5) . ? N3 C20 1.426(5) . ? N4 C5 1.268(5) . ? N8 C7 1.337(5) . ? N8 C9 1.467(5) . ? N8 C13 1.476(5) . ? C1 C2 1.531(6) . ? C1 C5 1.524(5) . ? C1 C6 1.538(5) . ? C5 C26 1.486(6) . ? C6 H6 1.0000 . ? C6 C7 1.529(5) . ? C6 C14 1.524(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.498(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.509(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.392(6) . ? C14 C19 1.374(6) . ? C15 H15 0.9500 . ? C15 C16 1.389(6) . ? C16 H16 0.9500 . ? C16 C17 1.376(7) . ? C17 C18 1.380(7) . ? C18 H18 0.9500 . ? C18 C19 1.398(6) . ? C19 H19 0.9500 . ? C20 C21 1.388(6) . ? C20 C25 1.374(6) . ? C21 H21 0.9500 . ? C21 C22 1.393(7) . ? C22 H22 0.9500 . ? C22 C23 1.376(9) . ? C23 H23 0.9500 . ? C23 C24 1.397(8) . ? C24 H24 0.9500 . ? C24 C25 1.377(6) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C31 H31 1.0000 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 O7 0.94(3) 1.70(3) 2.646(4) 176(6) 3_656 yes 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 Cl1 C17 C18 C19 -178.5(3) . . . . ? O1 C1 C2 O2 -63.6(5) . . . . ? O1 C1 C2 N3 112.3(3) . . . . ? O1 C1 C5 N4 -112.2(4) . . . . ? O1 C1 C5 C26 65.0(5) . . . . ? O1 C1 C6 C7 -171.3(3) . . . . ? O1 C1 C6 C14 64.1(4) . . . . ? O11 C12 C13 N8 -57.9(5) . . . . ? N3 N4 C5 C1 -1.2(4) . . . . ? N3 N4 C5 C26 -178.4(4) . . . . ? N3 C20 C21 C22 179.9(4) . . . . ? N3 C20 C25 C24 -179.6(4) . . . . ? N4 N3 C2 O2 -179.2(4) . . . . ? N4 N3 C2 C1 4.9(4) . . . . ? N4 N3 C20 C21 -171.8(4) . . . . ? N4 N3 C20 C25 6.0(5) . . . . ? N8 C9 C10 O11 56.3(5) . . . . ? C1 C6 C7 O7 -26.8(5) . . . . ? C1 C6 C7 N8 153.6(3) . . . . ? C1 C6 C14 C15 -79.7(4) . . . . ? C1 C6 C14 C19 100.6(4) . . . . ? C2 N3 N4 C5 -2.5(5) . . . . ? C2 N3 C20 C21 11.6(6) . . . . ? C2 N3 C20 C25 -170.6(4) . . . . ? C2 C1 C5 N4 3.9(4) . . . . ? C2 C1 C5 C26 -178.9(4) . . . . ? C2 C1 C6 C7 67.3(4) . . . . ? C2 C1 C6 C14 -57.4(4) . . . . ? C5 C1 C2 O2 179.2(4) . . . . ? C5 C1 C2 N3 -5.0(4) . . . . ? C5 C1 C6 C7 -48.8(4) . . . . ? C5 C1 C6 C14 -173.5(3) . . . . ? C6 C1 C2 O2 55.1(6) . . . . ? C6 C1 C2 N3 -129.1(3) . . . . ? C6 C1 C5 N4 129.2(4) . . . . ? C6 C1 C5 C26 -53.6(5) . . . . ? C6 C14 C15 C16 -179.1(4) . . . . ? C6 C14 C19 C18 178.4(4) . . . . ? C7 N8 C9 C10 114.4(5) . . . . ? C7 N8 C13 C12 -114.6(4) . . . . ? C7 C6 C14 C15 155.7(4) . . . . ? C7 C6 C14 C19 -24.0(5) . . . . ? C9 N8 C7 O7 -170.7(4) . . . . ? C9 N8 C7 C6 8.8(6) . . . . ? C9 N8 C13 C12 55.8(5) . . . . ? C10 O11 C12 C13 59.8(5) . . . . ? C12 O11 C10 C9 -59.1(5) . . . . ? C13 N8 C7 O7 -1.9(6) . . . . ? C13 N8 C7 C6 177.6(3) . . . . ? C13 N8 C9 C10 -55.3(5) . . . . ? C14 C6 C7 O7 98.9(4) . . . . ? C14 C6 C7 N8 -80.7(4) . . . . ? C14 C15 C16 C17 0.5(6) . . . . ? C15 C14 C19 C18 -1.3(6) . . . . ? C15 C16 C17 Cl1 177.8(3) . . . . ? C15 C16 C17 C18 -1.0(7) . . . . ? C16 C17 C18 C19 0.3(7) . . . . ? C17 C18 C19 C14 0.9(7) . . . . ? C19 C14 C15 C16 0.6(6) . . . . ? C20 N3 N4 C5 -179.7(3) . . . . ? C20 N3 C2 O2 -2.4(7) . . . . ? C20 N3 C2 C1 -178.3(4) . . . . ? C20 C21 C22 C23 -1.2(8) . . . . ? C21 C20 C25 C24 -1.7(6) . . . . ? C21 C22 C23 C24 -0.1(8) . . . . ? C22 C23 C24 C25 0.5(8) . . . . ? C23 C24 C25 C20 0.4(7) . . . . ? C25 C20 C21 C22 2.1(7) . . . . ?