# Supplementary Information (SI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2024 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_br26 _audit_block_doi 10.5517/ccdc.csd.cc2hh203 _database_code_depnum_ccdc_archive 'CCDC 2308384' loop_ _audit_author_name _audit_author_address 'Gregory Excoffier' ;Laboratoire de Chimie Organique Appliquee, groupe de Chimie Bioorganique Annaba Badji Mokhar Annaba Algeria ; _audit_update_record ; 2023-11-16 deposited with the CCDC. 2024-07-18 downloaded from the CCDC. ; _audit_creation_date 2023-11-15 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _shelx_SHELXL_version_number 2019/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C20 H20 O3' _chemical_formula_sum 'C20 H20 O3' _chemical_formula_weight 308.36 _chemical_absolute_configuration unk _chemical_melting_point ? _chemical_oxdiff_formula 'c20 h20 o3' 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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. ; _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_H-M_alt 'P c a 21' _space_group_name_Hall 'P 2c -2ac' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 18.2645(5) _cell_length_b 9.2078(2) _cell_length_c 9.6666(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1625.69(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1770 _cell_measurement_temperature 295 _cell_measurement_theta_max 74.5100 _cell_measurement_theta_min 4.7920 _shelx_estimated_absorpt_T_max 0.987 _shelx_estimated_absorpt_T_min 0.867 _exptl_absorpt_coefficient_mu 0.670 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.87609 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description needle _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_unetI/netI 0.0438 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6225 _diffrn_reflns_point_group_measured_fraction_full 0.738 _diffrn_reflns_point_group_measured_fraction_max 0.716 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.512 _diffrn_reflns_theta_min 4.803 _diffrn_ambient_temperature 295 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.6091 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.979 _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 -108.00 -40.00 0.50 2.50 -- -41.15 -71.00 -65.00 136 2 \w 118.00 160.00 0.50 25.00 -- 107.24 54.00-135.00 84 3 \w 56.00 138.00 0.50 25.00 -- 107.24 -71.00 -65.00 164 4 \w 32.00 108.00 0.50 25.00 -- 107.24-107.00-149.00 152 5 \w -39.00 -9.00 0.50 2.50 -- -41.15 125.00 60.00 60 6 \w -85.00 -44.00 0.50 2.50 -- -41.15 125.00 60.00 82 7 \w 29.00 87.00 0.50 2.50 -- 41.15-125.00 -30.00 116 8 \w 24.00 65.00 0.50 2.50 -- 41.15 -99.00 150.00 82 9 \w 119.00 175.00 0.50 25.00 -- 107.24 111.00 -90.00 112 10 \w 34.00 136.00 0.50 25.00 -- 107.24 -30.00 -90.00 204 11 \w 40.00 107.00 0.50 25.00 -- 107.24-111.00 120.00 134 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1330825000 _diffrn_orient_matrix_UB_12 0.0487322000 _diffrn_orient_matrix_UB_13 0.0291548000 _diffrn_orient_matrix_UB_21 0.0005297000 _diffrn_orient_matrix_UB_22 -0.0250874000 _diffrn_orient_matrix_UB_23 0.1521296000 _diffrn_orient_matrix_UB_31 0.1014306000 _diffrn_orient_matrix_UB_32 0.0641229000 _diffrn_orient_matrix_UB_33 0.0373381000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.376 _reflns_Friedel_fraction_full 0.438 _reflns_Friedel_fraction_max 0.418 _reflns_number_gt 1973 _reflns_number_total 2390 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _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 2014/5 (Sheldrick, 2014)' _refine_diff_density_max 0.128 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.032 _refine_ls_abs_structure_details ; Flack x determined using 427 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.2(4) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 2390 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0424 _refine_ls_restrained_S_all 1.045 _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^)+(0.0524P)^2^+0.0249P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1010 _refine_ls_wR_factor_ref 0.1106 _refine_special_details ? _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.a Ternary CH refined with riding coordinates: C1(H1) 2.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A, H11B) 2.c Aromatic/amide H refined with riding coordinates: C15(H15), C16(H16), C17(H17), C19(H19) 2.d Idealised Me refined as rotating group: C20(H20A,H20B,H20C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary ? 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 O1 O 0.37488(11) 0.6826(2) 0.7999(2) 0.0528(5) Uani 1 1 d . . . . . O2 O 0.39887(19) 0.2966(3) 0.4835(3) 0.0802(8) Uani 1 1 d . . . . . O3 O 0.57112(15) 0.7375(3) 0.4885(4) 0.0775(8) Uani 1 1 d . . . . . C1 C 0.43911(15) 0.5873(3) 0.5431(3) 0.0431(6) Uani 1 1 d . . . . . H1 H 0.479818 0.524177 0.515723 0.052 Uiso 1 1 calc R U . . . C2 C 0.38607(16) 0.4990(3) 0.6282(3) 0.0443(6) Uani 1 1 d . . . . . C3 C 0.3695(2) 0.3502(3) 0.5854(4) 0.0576(8) Uani 1 1 d . . . . . C4 C 0.3181(3) 0.2635(4) 0.6732(5) 0.0775(11) Uani 1 1 d . . . . . H4A H 0.346184 0.210098 0.741609 0.093 Uiso 1 1 calc R U . . . H4B H 0.292893 0.193383 0.615486 0.093 Uiso 1 1 calc R U . . . C5 C 0.2623(2) 0.3567(4) 0.7463(5) 0.0742(10) Uani 1 1 d . . . . . H5A H 0.232954 0.296675 0.807403 0.089 Uiso 1 1 calc R U . . . H5B H 0.229818 0.400485 0.678672 0.089 Uiso 1 1 calc R U . . . C6 C 0.29935(18) 0.4746(3) 0.8293(3) 0.0556(7) Uani 1 1 d . . . . . H6A H 0.263117 0.544365 0.860421 0.067 Uiso 1 1 calc R U . . . H6B H 0.322303 0.432310 0.910362 0.067 Uiso 1 1 calc R U . . . C7 C 0.35572(16) 0.5499(3) 0.7442(3) 0.0448(6) Uani 1 1 d . . . . . C8 C 0.43544(15) 0.7522(3) 0.7473(3) 0.0470(6) Uani 1 1 d . . . . . C9 C 0.4570(2) 0.8793(4) 0.8331(4) 0.0608(8) Uani 1 1 d . . . . . H9A H 0.482909 0.846037 0.914819 0.073 Uiso 1 1 calc R U . . . H9B H 0.413523 0.930882 0.863090 0.073 Uiso 1 1 calc R U . . . C10 C 0.5059(2) 0.9813(4) 0.7510(5) 0.0729(10) Uani 1 1 d . . . . . H10A H 0.476876 1.031579 0.681907 0.087 Uiso 1 1 calc R U . . . H10B H 0.526844 1.053351 0.812479 0.087 Uiso 1 1 calc R U . . . C11 C 0.5665(2) 0.8978(5) 0.6808(4) 0.0685(9) Uani 1 1 d . . . . . H11A H 0.595483 0.964182 0.625391 0.082 Uiso 1 1 calc R U . . . H11B H 0.598305 0.856147 0.750670 0.082 Uiso 1 1 calc R U . . . C12 C 0.53789(18) 0.7784(3) 0.5897(4) 0.0540(7) Uani 1 1 d . . . . . C13 C 0.46907(15) 0.7079(3) 0.6316(3) 0.0444(6) Uani 1 1 d . . . . . C14 C 0.40291(15) 0.6459(3) 0.4125(3) 0.0425(5) Uani 1 1 d . . . . . C15 C 0.42084(19) 0.5892(4) 0.2842(3) 0.0581(7) Uani 1 1 d . . . . . H15 H 0.455673 0.515888 0.276881 0.070 Uiso 1 1 calc R U . . . C16 C 0.3866(2) 0.6422(4) 0.1668(3) 0.0676(10) Uani 1 1 d . . . . . H16 H 0.398124 0.603349 0.080727 0.081 Uiso 1 1 calc R U . . . C17 C 0.3355(2) 0.7522(4) 0.1762(4) 0.0651(9) Uani 1 1 d . . . . . H17 H 0.312970 0.786588 0.096425 0.078 Uiso 1 1 calc R U . . . C18 C 0.31756(15) 0.8115(3) 0.3027(4) 0.0535(7) Uani 1 1 d . . . . . C19 C 0.35154(16) 0.7572(3) 0.4203(3) 0.0458(6) Uani 1 1 d . . . . . H19 H 0.339718 0.796122 0.506247 0.055 Uiso 1 1 calc R U . . . C20 C 0.2634(2) 0.9343(4) 0.3149(5) 0.0761(11) Uani 1 1 d . . . . . H20A H 0.245782 0.959907 0.224589 0.114 Uiso 1 1 calc R U . . . H20B H 0.286992 1.016899 0.356083 0.114 Uiso 1 1 calc R U . . . H20C H 0.223097 0.904422 0.371796 0.114 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 O1 0.0568(11) 0.0556(10) 0.0460(10) -0.0088(9) 0.0077(10) -0.0022(9) O2 0.114(2) 0.0533(13) 0.0729(17) -0.0182(13) 0.0241(17) -0.0046(14) O3 0.0633(15) 0.0919(18) 0.0773(17) -0.0109(16) 0.0207(14) -0.0109(13) C1 0.0451(12) 0.0448(13) 0.0393(13) -0.0020(10) 0.0027(10) 0.0070(11) C2 0.0505(14) 0.0413(12) 0.0411(13) 0.0030(10) -0.0021(12) 0.0030(10) C3 0.075(2) 0.0459(14) 0.0522(16) -0.0018(13) 0.0044(15) -0.0028(14) C4 0.108(3) 0.0499(17) 0.074(2) -0.0032(17) 0.016(2) -0.0209(18) C5 0.073(2) 0.071(2) 0.079(3) 0.002(2) 0.012(2) -0.0149(17) C6 0.0592(16) 0.0555(15) 0.0522(16) 0.0050(13) 0.0099(14) 0.0026(13) C7 0.0516(14) 0.0425(12) 0.0403(13) 0.0023(11) -0.0038(12) 0.0014(10) C8 0.0461(13) 0.0516(14) 0.0432(13) -0.0018(12) -0.0054(12) 0.0003(11) C9 0.0614(17) 0.0671(18) 0.0538(18) -0.0167(15) -0.0056(14) -0.0042(15) C10 0.078(2) 0.0601(17) 0.081(3) -0.0183(19) -0.007(2) -0.0131(16) C11 0.0607(19) 0.077(2) 0.068(2) 0.0005(18) -0.0069(17) -0.0222(17) C12 0.0478(15) 0.0608(16) 0.0533(16) 0.0067(14) -0.0027(13) -0.0004(13) C13 0.0438(13) 0.0479(13) 0.0414(13) 0.0013(11) -0.0046(11) 0.0027(11) C14 0.0460(13) 0.0441(12) 0.0375(12) 0.0027(11) -0.0002(11) -0.0041(11) C15 0.0685(18) 0.0608(16) 0.0449(15) -0.0043(14) 0.0038(14) 0.0042(14) C16 0.092(3) 0.076(2) 0.0352(15) -0.0047(15) -0.0015(16) -0.0018(19) C17 0.072(2) 0.074(2) 0.0492(17) 0.0175(16) -0.0166(15) -0.0122(17) C18 0.0438(13) 0.0526(14) 0.0640(17) 0.0165(15) -0.0048(14) -0.0068(12) C19 0.0452(13) 0.0493(15) 0.0429(13) 0.0026(12) 0.0012(11) -0.0010(11) C20 0.0589(18) 0.0721(19) 0.098(3) 0.030(2) -0.006(2) 0.0090(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 C7 1.380(4) . ? O1 C8 1.376(4) . ? O2 C3 1.225(5) . ? O3 C12 1.211(5) . ? C1 H1 0.9800 . ? C1 C2 1.508(4) . ? C1 C13 1.505(4) . ? C1 C14 1.524(4) . ? C2 C3 1.463(4) . ? C2 C7 1.336(4) . ? C3 C4 1.496(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C5 1.509(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C6 1.510(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 C7 1.489(4) . ? C8 C9 1.488(4) . ? C8 C13 1.340(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.519(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.509(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.502(5) . ? C12 C13 1.471(4) . ? C14 C15 1.385(4) . ? C14 C19 1.392(4) . ? C15 H15 0.9300 . ? C15 C16 1.385(5) . ? C16 H16 0.9300 . ? C16 C17 1.379(6) . ? C17 H17 0.9300 . ? C17 C18 1.378(6) . ? C18 C19 1.389(5) . ? C18 C20 1.507(5) . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 C8 O1 C7 118.2(2) . . ? C2 C1 H1 108.4 . . ? C2 C1 C14 111.3(2) . . ? C13 C1 H1 108.4 . . ? C13 C1 C2 108.8(2) . . ? C13 C1 C14 111.5(2) . . ? C14 C1 H1 108.4 . . ? C3 C2 C1 118.9(3) . . ? C7 C2 C1 122.4(3) . . ? C7 C2 C3 118.7(3) . . ? O2 C3 C2 120.9(3) . . ? O2 C3 C4 121.1(3) . . ? C2 C3 C4 118.0(3) . . ? C3 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C3 C4 C5 112.7(3) . . ? H4A C4 H4B 107.8 . . ? C5 C4 H4A 109.0 . . ? C5 C4 H4B 109.0 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C4 C5 C6 110.7(3) . . ? H5A C5 H5B 108.1 . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C7 C6 C5 110.6(3) . . ? C7 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? O1 C7 C6 111.8(2) . . ? C2 C7 O1 122.2(3) . . ? C2 C7 C6 126.0(3) . . ? O1 C8 C9 111.9(3) . . ? C13 C8 O1 122.4(3) . . ? C13 C8 C9 125.7(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 C10 110.5(3) . . ? H9A C9 H9B 108.1 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C11 C10 C9 110.6(3) . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C10 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? C12 C11 C10 112.4(3) . . ? C12 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? O3 C12 C11 121.8(3) . . ? O3 C12 C13 120.9(3) . . ? C13 C12 C11 117.3(3) . . ? C8 C13 C1 122.1(3) . . ? C8 C13 C12 119.2(3) . . ? C12 C13 C1 118.7(3) . . ? C15 C14 C1 120.4(3) . . ? C15 C14 C19 119.1(3) . . ? C19 C14 C1 120.5(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 C14 119.6(3) . . ? C16 C15 H15 120.2 . . ? C15 C16 H16 119.7 . . ? C17 C16 C15 120.7(3) . . ? C17 C16 H16 119.7 . . ? C16 C17 H17 119.7 . . ? C18 C17 C16 120.7(3) . . ? C18 C17 H17 119.7 . . ? C17 C18 C19 118.5(3) . . ? C17 C18 C20 121.5(3) . . ? C19 C18 C20 119.9(4) . . ? C14 C19 H19 119.3 . . ? C18 C19 C14 121.4(3) . . ? C18 C19 H19 119.3 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 O1 C8 C9 C10 -161.2(3) . . . . ? O1 C8 C13 C1 5.7(4) . . . . ? O1 C8 C13 C12 -173.7(3) . . . . ? O2 C3 C4 C5 -152.7(4) . . . . ? O3 C12 C13 C1 -2.3(5) . . . . ? O3 C12 C13 C8 177.2(3) . . . . ? C1 C2 C3 O2 1.2(5) . . . . ? C1 C2 C3 C4 178.5(3) . . . . ? C1 C2 C7 O1 -4.9(4) . . . . ? C1 C2 C7 C6 175.7(3) . . . . ? C1 C14 C15 C16 179.0(3) . . . . ? C1 C14 C19 C18 -179.6(3) . . . . ? C2 C1 C13 C8 -19.2(4) . . . . ? C2 C1 C13 C12 160.3(2) . . . . ? C2 C1 C14 C15 -108.4(3) . . . . ? C2 C1 C14 C19 71.8(3) . . . . ? C2 C3 C4 C5 29.9(6) . . . . ? C3 C2 C7 O1 172.5(3) . . . . ? C3 C2 C7 C6 -6.8(5) . . . . ? C3 C4 C5 C6 -54.6(5) . . . . ? C4 C5 C6 C7 48.0(4) . . . . ? C5 C6 C7 O1 162.0(3) . . . . ? C5 C6 C7 C2 -18.6(4) . . . . ? C7 O1 C8 C9 -169.8(3) . . . . ? C7 O1 C8 C13 10.7(4) . . . . ? C7 C2 C3 O2 -176.4(3) . . . . ? C7 C2 C3 C4 1.0(5) . . . . ? C8 O1 C7 C2 -11.2(4) . . . . ? C8 O1 C7 C6 168.3(3) . . . . ? C8 C9 C10 C11 -48.6(4) . . . . ? C9 C8 C13 C1 -173.7(3) . . . . ? C9 C8 C13 C12 6.9(4) . . . . ? C9 C10 C11 C12 56.0(5) . . . . ? C10 C11 C12 O3 151.2(4) . . . . ? C10 C11 C12 C13 -31.5(5) . . . . ? C11 C12 C13 C1 -179.6(3) . . . . ? C11 C12 C13 C8 -0.1(4) . . . . ? C13 C1 C2 C3 -158.6(3) . . . . ? C13 C1 C2 C7 18.8(4) . . . . ? C13 C1 C14 C15 130.0(3) . . . . ? C13 C1 C14 C19 -49.9(3) . . . . ? C13 C8 C9 C10 18.3(5) . . . . ? C14 C1 C2 C3 78.1(3) . . . . ? C14 C1 C2 C7 -104.5(3) . . . . ? C14 C1 C13 C8 104.0(3) . . . . ? C14 C1 C13 C12 -76.6(3) . . . . ? C14 C15 C16 C17 0.8(6) . . . . ? C15 C14 C19 C18 0.6(4) . . . . ? C15 C16 C17 C18 0.0(6) . . . . ? C16 C17 C18 C19 -0.6(5) . . . . ? C16 C17 C18 C20 178.3(3) . . . . ? C17 C18 C19 C14 0.3(4) . . . . ? C19 C14 C15 C16 -1.1(5) . . . . ? C20 C18 C19 C14 -178.7(3) . . . . ? _shelx_res_file ; TITL br26_auto_a.res in Pca2(1) br26.res created by SHELXL-2019/3 at 09:49:30 on 15-Nov-2023 REM Old TITL BR26_auto in Pbcm REM SHELXT solution in Pca2(1) REM R1 0.120, Rweak 0.253, Alpha 0.001, Orientation a =b, b =a, c =-c REM Flack x = -0.109 ( 0.334 ) from Parsons quotients REM Formula found by SHELXT: C19 O3 CELL 1.54184 18.2645 9.2078 9.6666 90 90 90 ZERR 4 0.0005 0.0002 0.0002 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,-Y,+Z SYMM 0.5-X,+Y,0.5+Z SFAC C H O UNIT 80 80 12 L.S. 10 PLAN 21 SIZE 0.02 0.04 0.22 TEMP 21.85 CONF MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.052400 0.024900 FVAR 0.90499 O1 3 0.374879 0.682597 0.799872 11.00000 0.05685 0.05555 = 0.04598 -0.00881 0.00765 -0.00218 O2 3 0.398873 0.296591 0.483537 11.00000 0.11445 0.05329 = 0.07285 -0.01817 0.02410 -0.00461 O3 3 0.571119 0.737475 0.488547 11.00000 0.06329 0.09187 = 0.07731 -0.01091 0.02068 -0.01093 C1 1 0.439109 0.587271 0.543106 11.00000 0.04512 0.04483 = 0.03928 -0.00195 0.00265 0.00702 AFIX 13 H1 2 0.479818 0.524177 0.515723 11.00000 -1.20000 AFIX 0 C2 1 0.386073 0.499046 0.628155 11.00000 0.05047 0.04125 = 0.04112 0.00304 -0.00210 0.00298 C3 1 0.369482 0.350182 0.585362 11.00000 0.07477 0.04589 = 0.05223 -0.00182 0.00444 -0.00283 C4 1 0.318142 0.263486 0.673229 11.00000 0.10844 0.04992 = 0.07409 -0.00319 0.01617 -0.02094 AFIX 23 H4A 2 0.346184 0.210098 0.741609 11.00000 -1.20000 H4B 2 0.292893 0.193383 0.615486 11.00000 -1.20000 AFIX 0 C5 1 0.262256 0.356734 0.746318 11.00000 0.07262 0.07073 = 0.07912 0.00190 0.01220 -0.01488 AFIX 23 H5A 2 0.232954 0.296675 0.807403 11.00000 -1.20000 H5B 2 0.229818 0.400485 0.678672 11.00000 -1.20000 AFIX 0 C6 1 0.299351 0.474603 0.829334 11.00000 0.05916 0.05550 = 0.05217 0.00503 0.00992 0.00263 AFIX 23 H6A 2 0.263117 0.544365 0.860421 11.00000 -1.20000 H6B 2 0.322303 0.432310 0.910362 11.00000 -1.20000 AFIX 0 C7 1 0.355719 0.549924 0.744189 11.00000 0.05157 0.04253 = 0.04032 0.00233 -0.00385 0.00137 C8 1 0.435440 0.752166 0.747302 11.00000 0.04608 0.05165 = 0.04319 -0.00180 -0.00536 0.00035 C9 1 0.457030 0.879304 0.833123 11.00000 0.06138 0.06708 = 0.05383 -0.01669 -0.00560 -0.00416 AFIX 23 H9A 2 0.482909 0.846037 0.914819 11.00000 -1.20000 H9B 2 0.413523 0.930882 0.863090 11.00000 -1.20000 AFIX 0 C10 1 0.505870 0.981256 0.750974 11.00000 0.07797 0.06006 = 0.08059 -0.01833 -0.00733 -0.01312 AFIX 23 H10A 2 0.476876 1.031579 0.681907 11.00000 -1.20000 H10B 2 0.526844 1.053351 0.812479 11.00000 -1.20000 AFIX 0 C11 1 0.566495 0.897772 0.680779 11.00000 0.06073 0.07712 = 0.06776 0.00052 -0.00688 -0.02221 AFIX 23 H11A 2 0.595483 0.964182 0.625391 11.00000 -1.20000 H11B 2 0.598305 0.856147 0.750670 11.00000 -1.20000 AFIX 0 C12 1 0.537887 0.778429 0.589700 11.00000 0.04777 0.06084 = 0.05330 0.00673 -0.00265 -0.00042 C13 1 0.469069 0.707948 0.631561 11.00000 0.04380 0.04788 = 0.04139 0.00135 -0.00461 0.00267 C14 1 0.402906 0.645881 0.412469 11.00000 0.04603 0.04408 = 0.03753 0.00272 -0.00015 -0.00409 C15 1 0.420840 0.589160 0.284163 11.00000 0.06845 0.06080 = 0.04494 -0.00433 0.00376 0.00419 AFIX 43 H15 2 0.455673 0.515888 0.276881 11.00000 -1.20000 AFIX 0 C16 1 0.386582 0.642230 0.166801 11.00000 0.09180 0.07574 = 0.03518 -0.00466 -0.00152 -0.00183 AFIX 43 H16 2 0.398124 0.603349 0.080727 11.00000 -1.20000 AFIX 0 C17 1 0.335516 0.752154 0.176208 11.00000 0.07171 0.07429 = 0.04923 0.01751 -0.01660 -0.01220 AFIX 43 H17 2 0.312970 0.786588 0.096425 11.00000 -1.20000 AFIX 0 C18 1 0.317562 0.811485 0.302652 11.00000 0.04380 0.05265 = 0.06399 0.01654 -0.00483 -0.00676 C19 1 0.351545 0.757213 0.420323 11.00000 0.04524 0.04934 = 0.04292 0.00257 0.00118 -0.00105 AFIX 43 H19 2 0.339718 0.796122 0.506247 11.00000 -1.20000 AFIX 0 C20 1 0.263450 0.934321 0.314890 11.00000 0.05887 0.07206 = 0.09750 0.02984 -0.00578 0.00902 AFIX 137 H20A 2 0.245782 0.959907 0.224589 11.00000 -1.50000 H20B 2 0.286992 1.016899 0.356083 11.00000 -1.50000 H20C 2 0.223097 0.904422 0.371796 11.00000 -1.50000 AFIX 0 HKLF 4 REM br26_auto_a.res in Pca2(1) REM wR2 = 0.1106, GooF = S = 1.045, Restrained GooF = 1.045 for all data REM R1 = 0.0424 for 1973 Fo > 4sig(Fo) and 0.0555 for all 2390 data REM 209 parameters refined using 1 restraints END WGHT 0.0523 0.0249 REM Highest difference peak 0.128, deepest hole -0.125, 1-sigma level 0.032 Q1 1 0.2554 0.9737 0.4121 11.00000 0.05 0.13 Q2 1 0.4206 0.6167 0.4806 11.00000 0.05 0.12 Q3 1 0.4444 0.7455 0.6633 11.00000 0.05 0.12 Q4 1 0.3453 0.5535 0.6652 11.00000 0.05 0.12 Q5 1 0.4692 0.7010 0.7069 11.00000 0.05 0.12 Q6 1 0.2736 0.3068 0.6360 11.00000 0.05 0.12 Q7 1 0.3704 0.6939 0.8935 11.00000 0.05 0.12 Q8 1 0.4034 0.8995 0.5362 11.00000 0.05 0.11 Q9 1 0.4986 1.0933 0.9574 11.00000 0.05 0.11 Q10 1 0.3916 0.5005 0.6916 11.00000 0.05 0.11 Q11 1 0.3159 0.1668 0.6162 11.00000 0.05 0.11 Q12 1 0.2905 0.5332 0.9214 11.00000 0.05 0.11 Q13 1 0.3941 0.5259 -0.0003 11.00000 0.05 0.11 Q14 1 0.2798 1.0136 0.2581 11.00000 0.05 0.10 Q15 1 0.4210 0.2978 0.5575 11.00000 0.05 0.10 Q16 1 0.4882 0.7474 0.6156 11.00000 0.05 0.10 Q17 1 0.6013 0.7760 0.7455 11.00000 0.05 0.10 Q18 1 0.4057 0.8373 1.0192 11.00000 0.05 0.10 Q19 1 0.5934 0.8066 0.7528 11.00000 0.05 0.10 Q20 1 0.2039 1.0791 0.4783 11.00000 0.05 0.09 Q21 1 0.4234 0.3829 0.4406 11.00000 0.05 0.09 ; _shelx_res_checksum 36718 _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 1.251 _oxdiff_exptl_absorpt_empirical_full_min 0.675