# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2021 ####################################################################### # # 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_i18082 _database_code_depnum_ccdc_archive 'CCDC 2082023' loop_ _audit_author_name _audit_author_address 'Kesatebrhan Haile Asressu' ;Academia Sinica Taiwan ; _audit_update_record ; 2021-05-06 deposited with the CCDC. 2021-08-12 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 N2' _chemical_formula_sum 'C22 H18 N2' _chemical_formula_weight 310.38 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_H-M_alt 'C c' _space_group_name_Hall 'C -2yc' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 10.7445(3) _cell_length_b 19.4078(5) _cell_length_c 8.7809(2) _cell_angle_alpha 90 _cell_angle_beta 112.9490(10) _cell_angle_gamma 90 _cell_volume 1686.13(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 7607 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.45 _exptl_crystal_description niddle _exptl_crystal_colour colourless _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.223 _exptl_crystal_F_000 656 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.245 _exptl_crystal_size_mid 0.099 _exptl_crystal_size_min 0.084 _exptl_absorpt_coefficient_mu 0.072 _shelx_estimated_absorpt_T_min 0.983 _shelx_estimated_absorpt_T_max 0.994 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.9987 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24629 _diffrn_reflns_av_unetI/netI 0.0316 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.764 _diffrn_reflns_theta_max 27.494 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.942 _diffrn_reflns_point_group_measured_fraction_full 0.954 _reflns_number_total 3652 _reflns_number_gt 3331 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.884 _reflns_Friedel_fraction_max 0.887 _reflns_Friedel_fraction_full 0.911 _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. Completness statistics refer to single and composite reflections containing twin component 1 only. ; _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 958)' _computing_publication_material 'WinGX publication routines (Farrugia, 2014)' _refine_special_details ; Refined as a 2-component inversion twin. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.6802P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 2(3) _chemical_absolute_configuration ad _refine_ls_number_reflns 3652 _refine_ls_number_parameters 223 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 N1 N 0.53057(17) 0.48640(9) 0.3924(2) 0.0171(4) Uani 1 1 d . . . . . H1 H 0.521(3) 0.5163(14) 0.311(4) 0.030(7) Uiso 1 1 d . . . . . N2 N 0.49254(18) 0.43381(8) 0.5938(2) 0.0172(3) Uani 1 1 d . . . . . C1 C 0.45827(19) 0.48640(10) 0.4888(2) 0.0172(4) Uani 1 1 d . . . . . C2 C 0.6145(2) 0.42955(10) 0.4339(2) 0.0180(4) Uani 1 1 d . . . . . C3 C 0.5908(2) 0.39754(10) 0.5608(2) 0.0173(4) Uani 1 1 d . . . . . C4 C 0.3619(2) 0.54176(11) 0.4802(2) 0.0195(4) Uani 1 1 d . . . . . C5 C 0.2378(2) 0.52841(12) 0.4920(3) 0.0244(5) Uani 1 1 d . . . . . C6 C 0.1545(3) 0.58469(13) 0.4837(3) 0.0342(6) Uani 1 1 d . . . . . H6 H 0.069661 0.576997 0.490930 0.041 Uiso 1 1 calc R U . . . C7 C 0.1920(3) 0.65125(14) 0.4652(4) 0.0389(6) Uani 1 1 d . . . . . H7 H 0.133536 0.688563 0.461246 0.047 Uiso 1 1 calc R U . . . C8 C 0.3140(3) 0.66369(12) 0.4526(3) 0.0332(6) Uani 1 1 d . . . . . H8 H 0.339639 0.709429 0.439295 0.040 Uiso 1 1 calc R U . . . C9 C 0.3989(2) 0.60904(11) 0.4594(3) 0.0245(5) Uani 1 1 d . . . . . H9 H 0.482720 0.617328 0.449952 0.029 Uiso 1 1 calc R U . . . C10 C 0.1907(2) 0.45666(13) 0.5083(3) 0.0306(5) Uani 1 1 d . . . . . H10A H 0.097769 0.458508 0.502215 0.046 Uiso 1 1 calc R U . . . H10B H 0.249824 0.437033 0.614863 0.046 Uiso 1 1 calc R U . . . H10C H 0.194050 0.427780 0.418406 0.046 Uiso 1 1 calc R U . . . C11 C 0.6982(2) 0.41303(11) 0.3409(2) 0.0191(4) Uani 1 1 d . . . . . C12 C 0.7640(2) 0.46496(12) 0.2914(3) 0.0233(5) Uani 1 1 d . . . . . H12 H 0.758525 0.511322 0.322907 0.028 Uiso 1 1 calc R U . . . C13 C 0.8376(2) 0.44924(13) 0.1960(3) 0.0289(5) Uani 1 1 d . . . . . H13 H 0.882438 0.484829 0.162955 0.035 Uiso 1 1 calc R U . . . C14 C 0.8456(2) 0.38175(14) 0.1493(3) 0.0324(6) Uani 1 1 d . . . . . H14 H 0.894711 0.371208 0.082745 0.039 Uiso 1 1 calc R U . . . C15 C 0.7823(2) 0.32986(13) 0.1991(3) 0.0298(5) Uani 1 1 d . . . . . H15 H 0.789300 0.283533 0.168378 0.036 Uiso 1 1 calc R U . . . C16 C 0.7084(2) 0.34501(12) 0.2938(3) 0.0245(5) Uani 1 1 d . . . . . H16 H 0.664446 0.309029 0.326942 0.029 Uiso 1 1 calc R U . . . C17 C 0.6548(2) 0.33682(10) 0.6608(3) 0.0187(4) Uani 1 1 d . . . . . C18 C 0.7901(2) 0.31962(11) 0.6971(3) 0.0227(4) Uani 1 1 d . . . . . H18 H 0.843258 0.347884 0.657515 0.027 Uiso 1 1 calc R U . . . C19 C 0.8469(2) 0.26162(11) 0.7905(3) 0.0272(5) Uani 1 1 d . . . . . H19 H 0.938435 0.250219 0.813322 0.033 Uiso 1 1 calc R U . . . C20 C 0.7716(2) 0.22002(11) 0.8511(3) 0.0276(5) Uani 1 1 d . . . . . H20 H 0.810835 0.180094 0.914136 0.033 Uiso 1 1 calc R U . . . C21 C 0.6388(2) 0.23722(12) 0.8189(3) 0.0264(5) Uani 1 1 d . . . . . H21 H 0.586847 0.209211 0.860808 0.032 Uiso 1 1 calc R U . . . C22 C 0.5810(2) 0.29514(11) 0.7257(3) 0.0215(4) Uani 1 1 d . . . . . H22 H 0.490057 0.306718 0.705610 0.026 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 N1 0.0185(9) 0.0186(8) 0.0151(8) 0.0006(7) 0.0074(7) 0.0020(7) N2 0.0180(8) 0.0175(8) 0.0158(8) -0.0007(6) 0.0062(7) 0.0025(6) C1 0.0194(10) 0.0182(10) 0.0143(10) -0.0023(7) 0.0069(8) 0.0002(8) C2 0.0188(10) 0.0178(9) 0.0168(10) -0.0022(8) 0.0063(8) 0.0020(8) C3 0.0165(10) 0.0174(9) 0.0173(10) -0.0019(7) 0.0058(8) 0.0009(8) C4 0.0226(10) 0.0212(10) 0.0133(9) -0.0011(8) 0.0054(8) 0.0048(8) C5 0.0227(11) 0.0296(12) 0.0201(11) -0.0032(9) 0.0075(9) 0.0053(9) C6 0.0260(12) 0.0392(14) 0.0360(14) -0.0039(11) 0.0106(11) 0.0106(11) C7 0.0379(14) 0.0329(13) 0.0421(15) -0.0019(11) 0.0115(12) 0.0191(11) C8 0.0414(15) 0.0222(11) 0.0343(13) 0.0011(10) 0.0129(11) 0.0089(10) C9 0.0303(12) 0.0221(11) 0.0216(11) 0.0003(8) 0.0104(9) 0.0045(9) C10 0.0216(11) 0.0363(13) 0.0344(14) 0.0006(10) 0.0116(10) 0.0011(10) C11 0.0161(10) 0.0251(11) 0.0159(10) 0.0002(8) 0.0061(8) 0.0041(8) C12 0.0209(10) 0.0296(12) 0.0185(10) 0.0034(9) 0.0069(8) 0.0042(9) C13 0.0218(11) 0.0441(14) 0.0238(12) 0.0109(10) 0.0120(10) 0.0052(10) C14 0.0268(12) 0.0509(15) 0.0238(12) 0.0038(11) 0.0147(10) 0.0138(11) C15 0.0318(13) 0.0349(13) 0.0236(12) -0.0047(10) 0.0116(10) 0.0106(10) C16 0.0243(11) 0.0257(11) 0.0236(12) -0.0031(9) 0.0094(9) 0.0030(9) C17 0.0216(10) 0.0169(9) 0.0163(9) -0.0037(7) 0.0061(8) 0.0006(8) C18 0.0197(10) 0.0217(10) 0.0235(11) -0.0013(8) 0.0051(9) -0.0001(8) C19 0.0203(11) 0.0252(12) 0.0291(12) -0.0030(9) 0.0020(9) 0.0041(9) C20 0.0292(12) 0.0166(10) 0.0271(12) 0.0018(9) 0.0003(9) 0.0036(9) C21 0.0296(12) 0.0215(11) 0.0241(11) 0.0009(9) 0.0062(9) -0.0039(9) C22 0.0203(10) 0.0211(10) 0.0205(10) 0.0008(8) 0.0053(8) 0.0002(8) _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 N1 C1 1.354(3) . ? N1 C2 1.381(3) . ? N1 H1 0.90(3) . ? N2 C1 1.327(3) . ? N2 C3 1.390(3) . ? C1 C4 1.473(3) . ? C2 C3 1.383(3) . ? C2 C11 1.467(3) . ? C3 C17 1.470(3) . ? C4 C9 1.397(3) . ? C4 C5 1.402(3) . ? C5 C6 1.396(3) . ? C5 C10 1.507(3) . ? C6 C7 1.381(4) . ? C6 H6 0.9500 . ? C7 C8 1.380(4) . ? C7 H7 0.9500 . ? C8 C9 1.385(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.394(3) . ? C11 C16 1.400(3) . ? C12 C13 1.391(3) . ? C12 H12 0.9500 . ? C13 C14 1.385(4) . ? C13 H13 0.9500 . ? C14 C15 1.378(4) . ? C14 H14 0.9500 . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.400(3) . ? C17 C18 1.402(3) . ? C18 C19 1.386(3) . ? C18 H18 0.9500 . ? C19 C20 1.388(3) . ? C19 H19 0.9500 . ? C20 C21 1.383(3) . ? C20 H20 0.9500 . ? C21 C22 1.386(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 N1 C2 108.00(17) . . ? C1 N1 H1 125.8(17) . . ? C2 N1 H1 126.0(17) . . ? C1 N2 C3 105.82(16) . . ? N2 C1 N1 111.27(17) . . ? N2 C1 C4 126.55(18) . . ? N1 C1 C4 122.06(18) . . ? N1 C2 C3 105.40(17) . . ? N1 C2 C11 120.41(18) . . ? C3 C2 C11 134.09(19) . . ? C2 C3 N2 109.48(17) . . ? C2 C3 C17 130.60(18) . . ? N2 C3 C17 119.88(17) . . ? C9 C4 C5 120.6(2) . . ? C9 C4 C1 117.27(19) . . ? C5 C4 C1 122.09(19) . . ? C6 C5 C4 117.4(2) . . ? C6 C5 C10 119.8(2) . . ? C4 C5 C10 122.8(2) . . ? C7 C6 C5 121.9(2) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C8 C7 C6 120.2(2) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 119.5(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 C4 120.4(2) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 118.79(19) . . ? C12 C11 C2 120.75(19) . . ? C16 C11 C2 120.40(19) . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 120.1(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 120.1(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.3(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.4(2) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C22 C17 C18 118.12(19) . . ? C22 C17 C3 119.93(18) . . ? C18 C17 C3 121.93(19) . . ? C19 C18 C17 120.4(2) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 120.7(2) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C21 C20 C19 119.4(2) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 120.3(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C17 121.0(2) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? _refine_diff_density_max 0.155 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.034 _shelx_res_file ; TITL i18082_a.res in Cc i18082.res created by SHELXL-2018/3 at 16:00:51 on 07-Jan-2021 REM Old TITL i18082 in Cc REM SHELXT solution in Cc REM R1 0.090, Rweak 0.030, Alpha 0.005, Orientation as input REM Flack x = -0.609 ( 1.003 ) from Parsons' quotients REM Formula found by SHELXT: C22 N2 CELL 0.71073 10.7445 19.4078 8.7809 90.000 112.949 90.000 ZERR 4.000 0.0003 0.0005 0.0002 0.000 0.001 0.000 LATT -7 SYMM X, -Y, 1/2+Z SFAC C H N UNIT 88 72 8 ACTA TEMP -173.150 SIZE 0.084 0.099 0.245 L.S. 10 BOND $H LIST 6 FMAP 2 PLAN 3 OMIT 1 1 0 OMIT -1 1 0 TWIN WGHT 0.035100 0.680200 BASF 1.96532 FVAR 0.79033 N1 3 0.530568 0.486405 0.392368 11.00000 0.01845 0.01865 = 0.01506 0.00063 0.00738 0.00199 H1 2 0.520925 0.516255 0.310748 11.00000 0.02975 N2 3 0.492536 0.433810 0.593779 11.00000 0.01797 0.01746 = 0.01583 -0.00067 0.00616 0.00249 C1 1 0.458271 0.486398 0.488842 11.00000 0.01939 0.01817 = 0.01431 -0.00230 0.00689 0.00025 C2 1 0.614459 0.429551 0.433934 11.00000 0.01879 0.01776 = 0.01685 -0.00216 0.00626 0.00196 C3 1 0.590763 0.397537 0.560827 11.00000 0.01650 0.01744 = 0.01730 -0.00186 0.00581 0.00093 C4 1 0.361907 0.541760 0.480229 11.00000 0.02265 0.02121 = 0.01329 -0.00109 0.00540 0.00484 C5 1 0.237774 0.528411 0.492038 11.00000 0.02274 0.02964 = 0.02012 -0.00318 0.00750 0.00529 C6 1 0.154508 0.584687 0.483704 11.00000 0.02602 0.03920 = 0.03599 -0.00389 0.01064 0.01058 AFIX 43 H6 2 0.069661 0.576997 0.490930 11.00000 -1.20000 AFIX 0 C7 1 0.191961 0.651251 0.465245 11.00000 0.03789 0.03290 = 0.04215 -0.00195 0.01150 0.01910 AFIX 43 H7 2 0.133536 0.688563 0.461246 11.00000 -1.20000 AFIX 0 C8 1 0.314015 0.663691 0.452601 11.00000 0.04143 0.02220 = 0.03428 0.00109 0.01285 0.00887 AFIX 43 H8 2 0.339639 0.709429 0.439295 11.00000 -1.20000 AFIX 0 C9 1 0.398897 0.609039 0.459441 11.00000 0.03026 0.02207 = 0.02155 0.00027 0.01038 0.00449 AFIX 43 H9 2 0.482720 0.617328 0.449952 11.00000 -1.20000 AFIX 0 C10 1 0.190742 0.456660 0.508303 11.00000 0.02163 0.03635 = 0.03440 0.00057 0.01163 0.00106 AFIX 137 H10A 2 0.097769 0.458508 0.502215 11.00000 -1.50000 H10B 2 0.249824 0.437033 0.614863 11.00000 -1.50000 H10C 2 0.194050 0.427780 0.418406 11.00000 -1.50000 AFIX 0 C11 1 0.698172 0.413033 0.340889 11.00000 0.01609 0.02513 = 0.01590 0.00016 0.00612 0.00405 C12 1 0.763981 0.464958 0.291368 11.00000 0.02092 0.02964 = 0.01855 0.00340 0.00695 0.00422 AFIX 43 H12 2 0.758525 0.511322 0.322907 11.00000 -1.20000 AFIX 0 C13 1 0.837595 0.449244 0.196019 11.00000 0.02182 0.04406 = 0.02385 0.01086 0.01203 0.00516 AFIX 43 H13 2 0.882438 0.484829 0.162955 11.00000 -1.20000 AFIX 0 C14 1 0.845551 0.381745 0.149258 11.00000 0.02681 0.05086 = 0.02384 0.00382 0.01472 0.01379 AFIX 43 H14 2 0.894711 0.371208 0.082745 11.00000 -1.20000 AFIX 0 C15 1 0.782280 0.329860 0.199058 11.00000 0.03177 0.03491 = 0.02359 -0.00465 0.01161 0.01057 AFIX 43 H15 2 0.789300 0.283533 0.168378 11.00000 -1.20000 AFIX 0 C16 1 0.708389 0.345012 0.293798 11.00000 0.02425 0.02566 = 0.02365 -0.00307 0.00939 0.00297 AFIX 43 H16 2 0.664446 0.309029 0.326942 11.00000 -1.20000 AFIX 0 C17 1 0.654785 0.336819 0.660808 11.00000 0.02164 0.01692 = 0.01628 -0.00375 0.00612 0.00063 C18 1 0.790147 0.319618 0.697142 11.00000 0.01973 0.02169 = 0.02354 -0.00126 0.00514 -0.00013 AFIX 43 H18 2 0.843258 0.347884 0.657515 11.00000 -1.20000 AFIX 0 C19 1 0.846915 0.261621 0.790530 11.00000 0.02029 0.02521 = 0.02908 -0.00298 0.00200 0.00412 AFIX 43 H19 2 0.938435 0.250219 0.813322 11.00000 -1.20000 AFIX 0 C20 1 0.771559 0.220016 0.851117 11.00000 0.02916 0.01660 = 0.02712 0.00182 0.00030 0.00357 AFIX 43 H20 2 0.810835 0.180094 0.914136 11.00000 -1.20000 AFIX 0 C21 1 0.638772 0.237223 0.818885 11.00000 0.02964 0.02155 = 0.02406 0.00091 0.00615 -0.00393 AFIX 43 H21 2 0.586847 0.209211 0.860808 11.00000 -1.20000 AFIX 0 C22 1 0.581029 0.295144 0.725707 11.00000 0.02033 0.02112 = 0.02054 0.00082 0.00533 0.00017 AFIX 43 H22 2 0.490057 0.306718 0.705610 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 REM i18082_a.res in Cc REM wR2 = 0.080825, GooF = S = 1.06424, Restrained GooF = 1.06393 for all data REM R1 = 0.033446 for 3331 Fo > 4sig(Fo) and 0.041873 for all 3652 data REM 223 parameters refined using 2 restraints END WGHT 0.0351 0.6804 REM Highest difference peak 0.155, deepest hole -0.164, 1-sigma level 0.034 Q1 1 0.4103 0.5189 0.4857 11.00000 0.05 0.15 Q2 1 0.7539 0.4326 0.3480 11.00000 0.05 0.14 Q3 1 0.6357 0.4248 0.5309 11.00000 0.05 0.14 ; _shelx_res_checksum 38312 ####################################################################### # # 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_i18259 _database_code_depnum_ccdc_archive 'CCDC 2098033' loop_ _audit_author_name _audit_author_address 'Kesatebrhan Haile Asressu' ;Academia Sinica Taiwan ; _audit_update_record ; 2021-07-21 deposited with the CCDC. 2021-08-12 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H20 N2' _chemical_formula_sum 'C19 H20 N2' _chemical_formula_weight 276.37 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' _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. ; 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' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.5878(5) _cell_length_b 9.2549(3) _cell_length_c 20.0075(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3071.52(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 9938 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 26.73 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.195 _exptl_crystal_F_000 1184 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.317 _exptl_crystal_size_mid 0.169 _exptl_crystal_size_min 0.167 _exptl_absorpt_coefficient_mu 0.070 _shelx_estimated_absorpt_T_min 0.978 _shelx_estimated_absorpt_T_max 0.988 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8011 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker D8 Venture PhotonIII' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 61188 _diffrn_reflns_av_unetI/netI 0.0263 _diffrn_reflns_av_R_equivalents 0.0853 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.036 _diffrn_reflns_theta_max 27.101 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 3375 _reflns_number_gt 2731 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _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. ; _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 958)' _computing_publication_material 'WinGX publication routines (Farrugia, 2014)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0357P)^2^+1.4127P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3375 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 N1 N 0.30994(7) 0.60788(11) 0.27097(5) 0.0182(2) Uani 1 1 d . . . . . N2 N 0.25898(7) 0.39119(11) 0.28928(5) 0.0179(2) Uani 1 1 d . . . . . H2 H 0.226381 0.316405 0.286575 0.021 Uiso 1 1 calc R U . . . C1 C 0.25052(8) 0.51756(13) 0.25631(6) 0.0182(3) Uani 1 1 d . . . . . C2 C 0.35854(8) 0.53552(13) 0.31651(6) 0.0171(3) Uani 1 1 d . . . . . C3 C 0.32785(8) 0.39981(13) 0.32805(6) 0.0173(3) Uani 1 1 d . . . . . C4 C 0.17888(8) 0.55381(14) 0.21409(7) 0.0214(3) Uani 1 1 d . . . . . H4A H 0.192489 0.638251 0.185887 0.026 Uiso 1 1 calc R U . . . H4AB H 0.134032 0.582726 0.243876 0.026 Uiso 1 1 calc R U . . . C5 C 0.14954(8) 0.43180(14) 0.16877(7) 0.0212(3) Uani 1 1 d . . . . . H5A H 0.139687 0.344819 0.196383 0.025 Uiso 1 1 calc R U . . . H5AB H 0.097527 0.460564 0.148474 0.025 Uiso 1 1 calc R U . . . C6 C 0.20830(9) 0.39314(16) 0.11324(7) 0.0269(3) Uani 1 1 d . . . . . H6A H 0.261471 0.370287 0.133071 0.032 Uiso 1 1 calc R U . . . H6AB H 0.215208 0.477623 0.083430 0.032 Uiso 1 1 calc R U . . . C7 C 0.17952(10) 0.26444(17) 0.07213(8) 0.0344(4) Uani 1 1 d . . . . . H7A H 0.127869 0.287952 0.050982 0.052 Uiso 1 1 calc R U . . . H7B H 0.172694 0.180457 0.101423 0.052 Uiso 1 1 calc R U . . . H7C H 0.219483 0.242164 0.037561 0.052 Uiso 1 1 calc R U . . . C8 C 0.42757(8) 0.61108(13) 0.34711(6) 0.0181(3) Uani 1 1 d . . . . . C9 C 0.47322(8) 0.70834(14) 0.30932(7) 0.0210(3) Uani 1 1 d . . . . . H9 H 0.460623 0.722811 0.263485 0.025 Uiso 1 1 calc R U . . . C10 C 0.53673(8) 0.78403(14) 0.33792(7) 0.0241(3) Uani 1 1 d . . . . . H10 H 0.567041 0.850199 0.311718 0.029 Uiso 1 1 calc R U . . . C11 C 0.55596(8) 0.76317(15) 0.40463(7) 0.0250(3) Uani 1 1 d . . . . . H11 H 0.599844 0.813954 0.424095 0.030 Uiso 1 1 calc R U . . . C12 C 0.51087(8) 0.66789(14) 0.44282(7) 0.0242(3) Uani 1 1 d . . . . . H12 H 0.523805 0.653870 0.488617 0.029 Uiso 1 1 calc R U . . . C13 C 0.44696(8) 0.59285(14) 0.41460(7) 0.0210(3) Uani 1 1 d . . . . . H13 H 0.416115 0.528545 0.441357 0.025 Uiso 1 1 calc R U . . . C14 C 0.35372(8) 0.27544(13) 0.36838(6) 0.0180(3) Uani 1 1 d . . . . . C15 C 0.43483(8) 0.23430(14) 0.37154(6) 0.0208(3) Uani 1 1 d . . . . . H15 H 0.474618 0.291305 0.349827 0.025 Uiso 1 1 calc R U . . . C16 C 0.45759(9) 0.11092(15) 0.40613(7) 0.0258(3) Uani 1 1 d . . . . . H16 H 0.512807 0.083999 0.407971 0.031 Uiso 1 1 calc R U . . . C17 C 0.40000(9) 0.02652(15) 0.43809(7) 0.0275(3) Uani 1 1 d . . . . . H17 H 0.415581 -0.058853 0.461073 0.033 Uiso 1 1 calc R U . . . C18 C 0.31982(9) 0.06766(15) 0.43623(7) 0.0254(3) Uani 1 1 d . . . . . H18 H 0.280394 0.010849 0.458492 0.030 Uiso 1 1 calc R U . . . C19 C 0.29659(8) 0.19145(14) 0.40202(6) 0.0210(3) Uani 1 1 d . . . . . H19 H 0.241462 0.219263 0.401472 0.025 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 N1 0.0205(5) 0.0146(5) 0.0194(5) 0.0004(4) -0.0014(4) 0.0021(4) N2 0.0193(5) 0.0136(5) 0.0207(5) 0.0011(4) -0.0019(4) -0.0004(4) C1 0.0220(6) 0.0135(6) 0.0191(6) -0.0003(5) -0.0007(5) 0.0023(5) C2 0.0189(6) 0.0159(6) 0.0165(6) 0.0000(5) -0.0006(5) 0.0024(5) C3 0.0188(6) 0.0165(6) 0.0166(6) -0.0007(5) -0.0007(5) 0.0016(5) C4 0.0223(7) 0.0170(6) 0.0249(7) 0.0019(5) -0.0043(5) 0.0018(5) C5 0.0218(7) 0.0181(6) 0.0237(6) 0.0034(5) -0.0044(5) -0.0014(5) C6 0.0310(8) 0.0254(7) 0.0243(7) 0.0003(6) -0.0006(6) -0.0025(6) C7 0.0439(9) 0.0311(8) 0.0283(8) -0.0046(6) -0.0041(7) -0.0007(7) C8 0.0181(6) 0.0143(6) 0.0219(6) -0.0024(5) 0.0003(5) 0.0032(5) C9 0.0213(7) 0.0188(6) 0.0229(6) -0.0002(5) -0.0001(5) 0.0024(5) C10 0.0211(7) 0.0178(6) 0.0336(7) -0.0013(6) 0.0032(6) 0.0001(5) C11 0.0205(7) 0.0197(6) 0.0348(8) -0.0083(6) -0.0042(6) 0.0014(5) C12 0.0274(7) 0.0228(7) 0.0224(7) -0.0046(5) -0.0053(5) 0.0055(6) C13 0.0243(7) 0.0169(6) 0.0219(6) -0.0018(5) 0.0006(5) 0.0024(5) C14 0.0244(7) 0.0139(6) 0.0158(6) -0.0016(5) -0.0017(5) 0.0010(5) C15 0.0247(7) 0.0168(6) 0.0209(6) -0.0025(5) -0.0015(5) 0.0012(5) C16 0.0290(7) 0.0200(7) 0.0284(7) -0.0035(6) -0.0068(6) 0.0056(6) C17 0.0405(8) 0.0171(6) 0.0251(7) 0.0025(5) -0.0075(6) 0.0052(6) C18 0.0357(8) 0.0188(7) 0.0217(7) 0.0018(5) -0.0005(6) -0.0024(6) C19 0.0233(7) 0.0199(6) 0.0196(6) 0.0001(5) -0.0008(5) 0.0009(5) _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 N1 C1 1.3252(17) . ? N1 C2 1.3889(16) . ? N2 C1 1.3501(16) . ? N2 C3 1.3831(16) . ? N2 H2 0.8800 . ? C1 C4 1.4960(18) . ? C2 C3 1.3748(17) . ? C2 C8 1.4746(18) . ? C3 C14 1.4697(17) . ? C4 C5 1.5278(18) . ? C4 H4A 0.9900 . ? C4 H4AB 0.9900 . ? C5 C6 1.521(2) . ? C5 H5A 0.9900 . ? C5 H5AB 0.9900 . ? C6 C7 1.524(2) . ? C6 H6A 0.9900 . ? C6 H6AB 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C13 1.3983(18) . ? C8 C9 1.3984(18) . ? C9 C10 1.3885(19) . ? C9 H9 0.9500 . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.386(2) . ? C11 H11 0.9500 . ? C12 C13 1.3874(19) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.3983(19) . ? C14 C15 1.3998(19) . ? C15 C16 1.3876(18) . ? C15 H15 0.9500 . ? C16 C17 1.390(2) . ? C16 H16 0.9500 . ? C17 C18 1.384(2) . ? C17 H17 0.9500 . ? C18 C19 1.3890(18) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? 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 N1 C2 105.83(10) . . ? C1 N2 C3 108.05(11) . . ? C1 N2 H2 126.0 . . ? C3 N2 H2 126.0 . . ? N1 C1 N2 111.16(11) . . ? N1 C1 C4 125.05(11) . . ? N2 C1 C4 123.56(12) . . ? C3 C2 N1 109.61(11) . . ? C3 C2 C8 130.63(11) . . ? N1 C2 C8 119.63(11) . . ? C2 C3 N2 105.34(11) . . ? C2 C3 C14 134.39(12) . . ? N2 C3 C14 120.25(11) . . ? C1 C4 C5 114.98(11) . . ? C1 C4 H4A 108.5 . . ? C5 C4 H4A 108.5 . . ? C1 C4 H4AB 108.5 . . ? C5 C4 H4AB 108.5 . . ? H4A C4 H4AB 107.5 . . ? C6 C5 C4 113.79(11) . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5AB 108.8 . . ? C4 C5 H5AB 108.8 . . ? H5A C5 H5AB 107.7 . . ? C5 C6 C7 112.17(12) . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6AB 109.2 . . ? C7 C6 H6AB 109.2 . . ? H6A C6 H6AB 107.9 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 118.37(12) . . ? C13 C8 C2 121.48(12) . . ? C9 C8 C2 120.08(11) . . ? C10 C9 C8 120.85(13) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C9 120.08(13) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.70(13) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 120.43(13) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 120.55(13) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C19 C14 C15 118.59(12) . . ? C19 C14 C3 120.12(12) . . ? C15 C14 C3 121.23(12) . . ? C16 C15 C14 120.52(13) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 120.34(13) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 119.57(13) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 120.45(13) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C14 120.51(13) . . ? C18 C19 H19 119.7 . . ? C14 C19 H19 119.7 . . ? _refine_diff_density_max 0.240 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.041 _shelx_res_file ; TITL i18259_a.res in Pbca i18259.res created by SHELXL-2018/3 at 18:06:57 on 08-Jul-2021 REM Old TITL i18259 in Pbca REM SHELXT solution in Pbca REM R1 0.120, Rweak 0.004, Alpha 0.018, Orientation as input REM Formula found by SHELXT: C19 N2 CELL 0.71073 16.5878 9.2549 20.0075 90.000 90.000 90.000 ZERR 8.000 0.0005 0.0003 0.0006 0.000 0.000 0.000 LATT 1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N UNIT 152 160 16 ACTA TEMP -173.150 SIZE 0.167 0.169 0.317 L.S. 10 BOND $H LIST 6 OMIT 9 3 6 FMAP 2 PLAN 5 WGHT 0.035700 1.412700 FVAR 0.48520 N1 3 0.309937 0.607882 0.270965 11.00000 0.02053 0.01462 = 0.01943 0.00036 -0.00144 0.00211 N2 3 0.258982 0.391189 0.289278 11.00000 0.01931 0.01363 = 0.02071 0.00108 -0.00187 -0.00039 AFIX 43 H2 2 0.226381 0.316405 0.286575 11.00000 -1.20000 AFIX 0 C1 1 0.250519 0.517557 0.256305 11.00000 0.02201 0.01352 = 0.01913 -0.00029 -0.00071 0.00230 C2 1 0.358545 0.535524 0.316515 11.00000 0.01889 0.01595 = 0.01655 0.00001 -0.00056 0.00239 C3 1 0.327847 0.399815 0.328047 11.00000 0.01884 0.01648 = 0.01656 -0.00068 -0.00068 0.00163 C4 1 0.178879 0.553813 0.214092 11.00000 0.02230 0.01704 = 0.02489 0.00186 -0.00426 0.00178 AFIX 23 H4A 2 0.192489 0.638251 0.185887 11.00000 -1.20000 H4AB 2 0.134032 0.582726 0.243876 11.00000 -1.20000 AFIX 0 C5 1 0.149542 0.431802 0.168766 11.00000 0.02184 0.01814 = 0.02370 0.00341 -0.00438 -0.00142 AFIX 23 H5A 2 0.139687 0.344819 0.196383 11.00000 -1.20000 H5AB 2 0.097527 0.460564 0.148474 11.00000 -1.20000 AFIX 0 C6 1 0.208301 0.393139 0.113236 11.00000 0.03098 0.02535 = 0.02433 0.00035 -0.00061 -0.00251 AFIX 23 H6A 2 0.261471 0.370287 0.133071 11.00000 -1.20000 H6AB 2 0.215208 0.477623 0.083430 11.00000 -1.20000 AFIX 0 C7 1 0.179518 0.264441 0.072132 11.00000 0.04395 0.03110 = 0.02827 -0.00457 -0.00408 -0.00075 AFIX 137 H7A 2 0.127869 0.287952 0.050982 11.00000 -1.50000 H7B 2 0.172694 0.180457 0.101423 11.00000 -1.50000 H7C 2 0.219483 0.242164 0.037561 11.00000 -1.50000 AFIX 0 C8 1 0.427567 0.611078 0.347110 11.00000 0.01813 0.01432 = 0.02189 -0.00236 0.00030 0.00316 C9 1 0.473222 0.708339 0.309317 11.00000 0.02133 0.01881 = 0.02293 -0.00018 -0.00009 0.00237 AFIX 43 H9 2 0.460623 0.722811 0.263485 11.00000 -1.20000 AFIX 0 C10 1 0.536731 0.784032 0.337915 11.00000 0.02105 0.01779 = 0.03358 -0.00128 0.00315 0.00007 AFIX 43 H10 2 0.567041 0.850199 0.311718 11.00000 -1.20000 AFIX 0 C11 1 0.555958 0.763173 0.404629 11.00000 0.02053 0.01973 = 0.03484 -0.00825 -0.00416 0.00136 AFIX 43 H11 2 0.599844 0.813954 0.424095 11.00000 -1.20000 AFIX 0 C12 1 0.510867 0.667889 0.442819 11.00000 0.02742 0.02278 = 0.02241 -0.00460 -0.00530 0.00547 AFIX 43 H12 2 0.523805 0.653870 0.488617 11.00000 -1.20000 AFIX 0 C13 1 0.446959 0.592850 0.414602 11.00000 0.02431 0.01688 = 0.02191 -0.00178 0.00058 0.00239 AFIX 43 H13 2 0.416115 0.528545 0.441357 11.00000 -1.20000 AFIX 0 C14 1 0.353715 0.275444 0.368377 11.00000 0.02441 0.01388 = 0.01583 -0.00160 -0.00170 0.00102 C15 1 0.434833 0.234304 0.371536 11.00000 0.02469 0.01676 = 0.02085 -0.00247 -0.00147 0.00119 AFIX 43 H15 2 0.474618 0.291305 0.349827 11.00000 -1.20000 AFIX 0 C16 1 0.457585 0.110919 0.406128 11.00000 0.02901 0.01998 = 0.02836 -0.00347 -0.00679 0.00559 AFIX 43 H16 2 0.512807 0.083999 0.407971 11.00000 -1.20000 AFIX 0 C17 1 0.400004 0.026522 0.438091 11.00000 0.04047 0.01708 = 0.02506 0.00255 -0.00752 0.00515 AFIX 43 H17 2 0.415581 -0.058853 0.461073 11.00000 -1.20000 AFIX 0 C18 1 0.319815 0.067660 0.436226 11.00000 0.03573 0.01882 = 0.02166 0.00178 -0.00050 -0.00242 AFIX 43 H18 2 0.280394 0.010849 0.458492 11.00000 -1.20000 AFIX 0 C19 1 0.296587 0.191449 0.402017 11.00000 0.02333 0.01994 = 0.01960 0.00007 -0.00080 0.00093 AFIX 43 H19 2 0.241462 0.219263 0.401472 11.00000 -1.20000 AFIX 0 HKLF 4 REM i18259_a.res in Pbca REM wR2 = 0.097224, GooF = S = 1.05555, Restrained GooF = 1.05555 for all data REM R1 = 0.039759 for 2731 Fo > 4sig(Fo) and 0.052926 for all 3375 data REM 191 parameters refined using 0 restraints END WGHT 0.0357 1.4122 REM Highest difference peak 0.240, deepest hole -0.210, 1-sigma level 0.041 Q1 1 0.3890 0.5663 0.3364 11.00000 0.05 0.24 Q2 1 0.3560 0.4580 0.3152 11.00000 0.05 0.21 Q3 1 0.4422 0.5994 0.3801 11.00000 0.05 0.19 Q4 1 0.3075 0.7007 0.2732 11.00000 0.05 0.18 Q5 1 0.1856 0.4030 0.1476 11.00000 0.05 0.18 ; _shelx_res_checksum 40366 ####################################################################### # # 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_i18116 _database_code_depnum_ccdc_archive 'CCDC 2082036' loop_ _audit_author_name _audit_author_address 'Kesatebrhan Haile Asressu' ;Academia Sinica Taiwan ; _audit_update_record ; 2021-05-06 deposited with the CCDC. 2021-08-12 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H12 N2 S2' _chemical_formula_sum 'C17 H12 N2 S2' _chemical_formula_weight 308.41 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _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. ; 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' _cell_length_a 11.1404(4) _cell_length_b 14.6012(6) _cell_length_c 9.2447(3) _cell_angle_alpha 90 _cell_angle_beta 104.4970(10) _cell_angle_gamma 90 _cell_volume 1455.89(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 7244 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.84 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.407 _exptl_crystal_F_000 640 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.058 _exptl_absorpt_coefficient_mu 0.359 _shelx_estimated_absorpt_T_min 0.928 _shelx_estimated_absorpt_T_max 0.979 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9613 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 42960 _diffrn_reflns_av_unetI/netI 0.0297 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.669 _diffrn_reflns_theta_max 27.102 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 3206 _reflns_number_gt 2634 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _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. ; _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 958)' _computing_publication_material 'WinGX publication routines (Farrugia, 2014)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+1.7264P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3206 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0999 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.36499(5) 0.38289(4) 0.90631(6) 0.02401(15) Uani 1 1 d . . . . . S2 S 0.41483(9) 0.46698(6) 0.27715(10) 0.0287(3) Uani 0.463(3) 1 d . . P A 1 C15 C 0.22956(9) 0.46729(7) 0.42686(10) 0.0337(3) Uani 0.463(3) 1 d . . P A 1 H15 H 0.180595 0.456685 0.495850 0.040 Uiso 0.463(3) 1 calc R U P A 1 S2' S 0.22956(9) 0.46729(7) 0.42686(10) 0.0337(3) Uani 0.537(3) 1 d . . P A 2 C15' C 0.41483(9) 0.46698(6) 0.27715(10) 0.0287(3) Uani 0.537(3) 1 d . . P A 2 H15' H 0.488881 0.455736 0.246765 0.034 Uiso 0.537(3) 1 calc R U P A 2 N1 N 0.52169(15) 0.26467(11) 0.69835(17) 0.0156(3) Uani 1 1 d . . . . . H1 H 0.537703 0.233279 0.782260 0.019 Uiso 1 1 calc R U . . . N2 N 0.54180(14) 0.32022(11) 0.48280(17) 0.0152(3) Uani 1 1 d . . . . . C1 C 0.59125(18) 0.26585(13) 0.5978(2) 0.0150(4) Uani 1 1 d . . . . . C2 C 0.42126(17) 0.32133(13) 0.6462(2) 0.0163(4) Uani 1 1 d . . . . . C3 C 0.43542(18) 0.35566(13) 0.5123(2) 0.0158(4) Uani 1 1 d . . . . . C4 C 0.70667(17) 0.21375(13) 0.6133(2) 0.0161(4) Uani 1 1 d . . . . . C5 C 0.79329(19) 0.24422(15) 0.5378(2) 0.0209(4) Uani 1 1 d . . . . . H5 H 0.777193 0.298013 0.478238 0.025 Uiso 1 1 calc R U . . . C6 C 0.9021(2) 0.19638(17) 0.5494(2) 0.0280(5) Uani 1 1 d . . . . . H6 H 0.959568 0.216534 0.495694 0.034 Uiso 1 1 calc R U . . . C7 C 0.9280(2) 0.11927(17) 0.6387(3) 0.0302(5) Uani 1 1 d . . . . . H7 H 1.003907 0.087404 0.647838 0.036 Uiso 1 1 calc R U . . . C8 C 0.8436(2) 0.08860(15) 0.7146(2) 0.0264(5) Uani 1 1 d . . . . . H8 H 0.861637 0.035736 0.776107 0.032 Uiso 1 1 calc R U . . . C9 C 0.73201(19) 0.13508(14) 0.7011(2) 0.0204(4) Uani 1 1 d . . . . . H9 H 0.673279 0.113132 0.751639 0.024 Uiso 1 1 calc R U . . . C10 C 0.32739(19) 0.33514(13) 0.7298(2) 0.0180(4) Uani 1 1 d . . . . . C11 C 0.2032(2) 0.31147(15) 0.6872(2) 0.0240(5) Uani 1 1 d . . . . . H11 H 0.163995 0.284456 0.593861 0.029 Uiso 1 1 calc R U . . . C12 C 0.1413(2) 0.33271(15) 0.8010(3) 0.0266(5) Uani 1 1 d . . . . . H12 H 0.055668 0.321364 0.791111 0.032 Uiso 1 1 calc R U . . . C13 C 0.2166(2) 0.37048(15) 0.9238(2) 0.0254(5) Uani 1 1 d . . . . . H13 H 0.190326 0.388118 1.009905 0.031 Uiso 1 1 calc R U . . . C14 C 0.36234(19) 0.42312(14) 0.4113(2) 0.0181(4) Uani 1 1 d . . . . . C16 C 0.2118(2) 0.53417(17) 0.2856(3) 0.0343(6) Uani 1 1 d . . . . . H16 H 0.140564 0.571921 0.253874 0.041 Uiso 1 1 calc R U . A 1 C17 C 0.3036(2) 0.53385(15) 0.2142(2) 0.0293(5) Uani 1 1 d . . . . . H17 H 0.301062 0.572036 0.130300 0.035 Uiso 1 1 calc R U . A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0257(3) 0.0288(3) 0.0187(3) -0.0029(2) 0.0079(2) 0.0037(2) S2 0.0358(6) 0.0232(5) 0.0227(5) 0.0037(4) -0.0009(4) 0.0018(4) C15 0.0320(5) 0.0355(6) 0.0317(5) 0.0076(4) 0.0043(4) 0.0077(4) S2' 0.0320(5) 0.0355(6) 0.0317(5) 0.0076(4) 0.0043(4) 0.0077(4) C15' 0.0358(6) 0.0232(5) 0.0227(5) 0.0037(4) -0.0009(4) 0.0018(4) N1 0.0177(8) 0.0177(8) 0.0121(7) 0.0009(6) 0.0048(6) 0.0011(6) N2 0.0179(8) 0.0161(8) 0.0115(7) -0.0011(6) 0.0033(6) -0.0009(6) C1 0.0170(9) 0.0158(9) 0.0123(8) -0.0025(7) 0.0037(7) -0.0035(7) C2 0.0173(9) 0.0178(10) 0.0137(9) -0.0032(7) 0.0035(7) 0.0003(8) C3 0.0179(9) 0.0167(9) 0.0127(9) -0.0026(7) 0.0039(7) -0.0006(7) C4 0.0169(9) 0.0189(10) 0.0120(8) -0.0041(7) 0.0027(7) -0.0012(8) C5 0.0214(10) 0.0257(11) 0.0157(9) -0.0011(8) 0.0048(8) -0.0025(8) C6 0.0192(10) 0.0400(13) 0.0265(11) -0.0053(10) 0.0089(9) -0.0038(9) C7 0.0207(11) 0.0379(13) 0.0304(12) -0.0086(10) 0.0035(9) 0.0082(10) C8 0.0309(12) 0.0233(11) 0.0230(11) -0.0014(9) 0.0027(9) 0.0084(9) C9 0.0235(10) 0.0202(10) 0.0181(9) -0.0012(8) 0.0065(8) 0.0009(8) C10 0.0238(10) 0.0178(10) 0.0139(9) 0.0002(7) 0.0072(8) 0.0022(8) C11 0.0260(11) 0.0273(11) 0.0221(10) -0.0024(9) 0.0128(9) 0.0003(9) C12 0.0237(11) 0.0275(12) 0.0322(12) -0.0007(9) 0.0138(9) -0.0005(9) C13 0.0325(12) 0.0233(11) 0.0249(11) 0.0000(9) 0.0153(9) 0.0039(9) C14 0.0215(10) 0.0179(9) 0.0138(9) -0.0022(8) 0.0026(7) 0.0009(8) C16 0.0287(12) 0.0312(13) 0.0355(13) -0.0097(10) -0.0062(10) 0.0109(10) C17 0.0440(14) 0.0220(11) 0.0179(10) 0.0012(8) 0.0000(9) -0.0064(10) _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 S1 C13 1.710(2) . ? S1 C10 1.7265(19) . ? S2 C17 1.571(3) . ? S2 C14 1.629(2) . ? C15 C16 1.603(3) . ? C15 C14 1.653(2) . ? C15 H15 0.9500 . ? S2' C16 1.603(3) . ? S2' C14 1.653(2) . ? C15' C17 1.571(3) . ? C15' C14 1.629(2) . ? C15' H15' 0.9500 . ? N1 C1 1.351(2) . ? N1 C2 1.378(2) . ? N1 H1 0.8800 . ? N2 C1 1.330(2) . ? N2 C3 1.381(2) . ? C1 C4 1.470(3) . ? C2 C3 1.381(3) . ? C2 C10 1.462(3) . ? C3 C14 1.458(3) . ? C4 C9 1.394(3) . ? C4 C5 1.398(3) . ? C5 C6 1.379(3) . ? C5 H5 0.9500 . ? C6 C7 1.383(3) . ? C6 H6 0.9500 . ? C7 C8 1.381(3) . ? C7 H7 0.9500 . ? C8 C9 1.394(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.384(3) . ? C11 C12 1.428(3) . ? C11 H11 0.9500 . ? C12 C13 1.349(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C16 C17 1.349(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? 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 C13 S1 C10 92.01(10) . . ? C17 S2 C14 97.24(12) . . ? C16 C15 C14 95.60(12) . . ? C16 C15 H15 132.2 . . ? C14 C15 H15 132.2 . . ? C16 S2' C14 95.60(12) . . ? C17 C15' C14 97.24(12) . . ? C17 C15' H15' 131.4 . . ? C14 C15' H15' 131.4 . . ? C1 N1 C2 107.87(15) . . ? C1 N1 H1 126.1 . . ? C2 N1 H1 126.1 . . ? C1 N2 C3 105.66(15) . . ? N2 C1 N1 111.30(17) . . ? N2 C1 C4 124.35(17) . . ? N1 C1 C4 124.35(17) . . ? N1 C2 C3 105.46(16) . . ? N1 C2 C10 121.57(17) . . ? C3 C2 C10 132.98(18) . . ? C2 C3 N2 109.71(17) . . ? C2 C3 C14 130.45(18) . . ? N2 C3 C14 119.73(16) . . ? C9 C4 C5 119.24(18) . . ? C9 C4 C1 121.90(18) . . ? C5 C4 C1 118.87(18) . . ? C6 C5 C4 120.2(2) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 120.5(2) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C4 C9 C8 120.0(2) . . ? C4 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C2 127.68(18) . . ? C11 C10 S1 111.02(15) . . ? C2 C10 S1 121.27(15) . . ? C10 C11 C12 111.62(19) . . ? C10 C11 H11 124.2 . . ? C12 C11 H11 124.2 . . ? C13 C12 C11 113.3(2) . . ? C13 C12 H12 123.4 . . ? C11 C12 H12 123.4 . . ? C12 C13 S1 112.07(16) . . ? C12 C13 H13 124.0 . . ? S1 C13 H13 124.0 . . ? C3 C14 S2 120.27(15) . . ? C3 C14 C15' 120.27(15) . . ? C3 C14 C15 125.21(15) . . ? S2 C14 C15 114.37(12) . . ? C3 C14 S2' 125.21(15) . . ? C15' C14 S2' 114.37(12) . . ? C17 C16 C15 116.25(19) . . ? C17 C16 S2' 116.25(19) . . ? C17 C16 H16 121.9 . . ? C15 C16 H16 121.9 . . ? C16 C17 S2 116.47(18) . . ? C16 C17 C15' 116.47(18) . . ? C16 C17 H17 121.8 . . ? S2 C17 H17 121.8 . . ? _refine_diff_density_max 0.593 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.060 _shelx_res_file ; TITL i18116_a.res in P2(1)/c i18116.res created by SHELXL-2018/3 at 23:16:17 on 04-Feb-2021 CELL 0.71073 11.1404 14.6012 9.2447 90.000 104.497 90.000 ZERR 4.00 0.0004 0.0006 0.0003 0.000 0.001 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N S UNIT 68 48 8 8 ACTA MERG 2 EXYZ S2 C15' EADP S2 C15' EXYZ S2' C15 EADP S2' C15 FMAP 2 PLAN 3 SIZE 0.058 0.160 0.210 BOND $H LIST 6 L.S. 10 TEMP -173.15 WGHT 0.037800 1.726400 FVAR 0.58995 0.46273 S1 4 0.364993 0.382886 0.906311 11.00000 0.02574 0.02883 = 0.01870 -0.00287 0.00789 0.00370 PART 1 S2 4 0.414826 0.466979 0.277149 21.00000 0.03577 0.02321 = 0.02273 0.00365 -0.00094 0.00179 C15 1 0.229561 0.467291 0.426861 21.00000 0.03195 0.03549 = 0.03169 0.00760 0.00426 0.00767 AFIX 43 H15 2 0.180595 0.456685 0.495850 21.00000 -1.20000 AFIX 0 PART 2 S2' 4 0.229561 0.467291 0.426861 -21.00000 0.03195 0.03549 = 0.03169 0.00760 0.00426 0.00767 C15' 1 0.414826 0.466979 0.277149 -21.00000 0.03577 0.02321 = 0.02273 0.00365 -0.00094 0.00179 AFIX 43 H15' 2 0.488881 0.455736 0.246765 -21.00000 -1.20000 AFIX 0 PART 0 N1 3 0.521695 0.264667 0.698346 11.00000 0.01769 0.01770 = 0.01209 0.00089 0.00483 0.00109 AFIX 43 H1 2 0.537703 0.233279 0.782260 11.00000 -1.20000 AFIX 0 N2 3 0.541801 0.320219 0.482804 11.00000 0.01791 0.01609 = 0.01150 -0.00111 0.00329 -0.00094 C1 1 0.591245 0.265850 0.597754 11.00000 0.01705 0.01580 = 0.01231 -0.00254 0.00371 -0.00353 C2 1 0.421255 0.321335 0.646202 11.00000 0.01732 0.01778 = 0.01372 -0.00323 0.00346 0.00030 C3 1 0.435421 0.355656 0.512300 11.00000 0.01791 0.01669 = 0.01270 -0.00262 0.00390 -0.00058 C4 1 0.706669 0.213754 0.613336 11.00000 0.01689 0.01886 = 0.01195 -0.00408 0.00274 -0.00123 C5 1 0.793294 0.244219 0.537762 11.00000 0.02144 0.02567 = 0.01567 -0.00109 0.00477 -0.00250 AFIX 43 H5 2 0.777193 0.298013 0.478238 11.00000 -1.20000 AFIX 0 C6 1 0.902072 0.196381 0.549393 11.00000 0.01924 0.04000 = 0.02647 -0.00530 0.00890 -0.00378 AFIX 43 H6 2 0.959568 0.216534 0.495694 11.00000 -1.20000 AFIX 0 C7 1 0.928022 0.119266 0.638705 11.00000 0.02070 0.03788 = 0.03043 -0.00860 0.00345 0.00823 AFIX 43 H7 2 1.003907 0.087404 0.647838 11.00000 -1.20000 AFIX 0 C8 1 0.843626 0.088602 0.714579 11.00000 0.03089 0.02326 = 0.02296 -0.00140 0.00269 0.00836 AFIX 43 H8 2 0.861637 0.035736 0.776107 11.00000 -1.20000 AFIX 0 C9 1 0.732010 0.135081 0.701070 11.00000 0.02353 0.02025 = 0.01813 -0.00117 0.00651 0.00090 AFIX 43 H9 2 0.673279 0.113132 0.751639 11.00000 -1.20000 AFIX 0 C10 1 0.327394 0.335141 0.729846 11.00000 0.02378 0.01780 = 0.01388 0.00020 0.00721 0.00220 C11 1 0.203209 0.311475 0.687213 11.00000 0.02603 0.02734 = 0.02213 -0.00238 0.01284 0.00026 AFIX 43 H11 2 0.163995 0.284456 0.593861 11.00000 -1.20000 AFIX 0 C12 1 0.141310 0.332706 0.800962 11.00000 0.02371 0.02749 = 0.03216 -0.00074 0.01383 -0.00051 AFIX 43 H12 2 0.055668 0.321364 0.791111 11.00000 -1.20000 AFIX 0 C13 1 0.216630 0.370483 0.923807 11.00000 0.03250 0.02331 = 0.02488 -0.00001 0.01535 0.00389 AFIX 43 H13 2 0.190326 0.388118 1.009905 11.00000 -1.20000 AFIX 0 C14 1 0.362339 0.423125 0.411301 11.00000 0.02151 0.01786 = 0.01380 -0.00224 0.00256 0.00091 C16 1 0.211769 0.534174 0.285562 11.00000 0.02869 0.03121 = 0.03552 -0.00966 -0.00620 0.01093 AFIX 43 H16 2 0.140564 0.571921 0.253874 11.00000 -1.20000 AFIX 0 C17 1 0.303562 0.533846 0.214200 11.00000 0.04400 0.02203 = 0.01789 0.00120 0.00002 -0.00641 AFIX 43 H17 2 0.301062 0.572036 0.130300 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 REM i18116_a.res in P2(1)/c REM wR2 = 0.106521, GooF = S = 1.04905, Restrained GooF = 1.04905 for all data REM R1 = 0.042667 for 2634 Fo > 4sig(Fo) and 0.056592 for all 3206 data REM 191 parameters refined using 0 restraints END WGHT 0.0378 1.7264 REM Highest difference peak 0.593, deepest hole -0.453, 1-sigma level 0.060 Q1 1 0.3838 0.4467 0.3388 11.00000 0.05 0.59 Q2 1 0.2859 0.4406 0.3933 11.00000 0.05 0.54 Q3 1 0.1765 0.3265 0.7354 11.00000 0.05 0.33 ; _shelx_res_checksum 69784 ####################################################################### # # 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_i18083 _database_code_depnum_ccdc_archive 'CCDC 2082025' loop_ _audit_author_name _audit_author_address 'Kesatebrhan Haile Asressu' ;Academia Sinica Taiwan ; _audit_update_record ; 2021-05-06 deposited with the CCDC. 2021-08-12 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H19 Br N2 O2' _chemical_formula_sum 'C23 H19 Br N2 O2' _chemical_formula_weight 435.31 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _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. ; 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' _cell_length_a 9.2089(2) _cell_length_b 19.8306(3) _cell_length_c 10.4519(2) _cell_angle_alpha 90 _cell_angle_beta 101.4920(10) _cell_angle_gamma 90 _cell_volume 1870.44(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 9959 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 30.37 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.546 _exptl_crystal_F_000 888 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.201 _exptl_crystal_size_mid 0.185 _exptl_crystal_size_min 0.095 _exptl_absorpt_coefficient_mu 2.220 _shelx_estimated_absorpt_T_min 0.664 _shelx_estimated_absorpt_T_max 0.817 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9203 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 78302 _diffrn_reflns_av_unetI/netI 0.0239 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.054 _diffrn_reflns_theta_max 30.518 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 5710 _reflns_number_gt 4848 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _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. ; _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 958)' _computing_publication_material 'WinGX publication routines (Farrugia, 2014)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+1.2629P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5710 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0603 _refine_ls_wR_factor_gt 0.0562 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Br1 Br 0.06714(2) 0.70917(2) 0.37315(2) 0.01563(4) Uani 1 1 d . . . . . O1 O 0.35295(13) 0.90293(5) 0.66112(10) 0.0192(2) Uani 1 1 d . . . . . O2 O 0.45954(12) 0.82430(5) 0.85330(10) 0.0168(2) Uani 1 1 d . . . . . N1 N 0.27095(14) 0.58394(6) 0.50626(12) 0.0137(2) Uani 1 1 d . . . . . H1 H 0.292(2) 0.5988(10) 0.4354(19) 0.022(5) Uiso 1 1 d . . . . . N2 N 0.23286(13) 0.58527(6) 0.70915(11) 0.0136(2) Uani 1 1 d . . . . . C1 C 0.25918(15) 0.62254(7) 0.61140(13) 0.0131(2) Uani 1 1 d . . . . . C2 C 0.22511(15) 0.51955(7) 0.66374(13) 0.0130(2) Uani 1 1 d . . . . . C3 C 0.24821(15) 0.51771(7) 0.53698(13) 0.0130(2) Uani 1 1 d . . . . . C4 C 0.27628(15) 0.69633(6) 0.61644(13) 0.0128(2) Uani 1 1 d . . . . . C5 C 0.20854(15) 0.74037(7) 0.51925(13) 0.0132(2) Uani 1 1 d . . . . . C6 C 0.23443(16) 0.80974(7) 0.52823(14) 0.0145(3) Uani 1 1 d . . . . . H6 H 0.191923 0.838617 0.458222 0.017 Uiso 1 1 calc R U . . . C7 C 0.32245(16) 0.83611(7) 0.63985(14) 0.0140(3) Uani 1 1 d . . . . . C8 C 0.38447(15) 0.79287(7) 0.74337(13) 0.0135(2) Uani 1 1 d . . . . . C9 C 0.36472(16) 0.72404(7) 0.72961(13) 0.0136(3) Uani 1 1 d . . . . . H9 H 0.411567 0.694927 0.797611 0.016 Uiso 1 1 calc R U . . . C10 C 0.3483(2) 0.94414(8) 0.54884(17) 0.0295(4) Uani 1 1 d . . . . . H10A H 0.402465 0.921890 0.488877 0.044 Uiso 1 1 calc R U . . . H10B H 0.394332 0.987826 0.575451 0.044 Uiso 1 1 calc R U . . . H10C H 0.245048 0.951060 0.504922 0.044 Uiso 1 1 calc R U . . . C11 C 0.55751(17) 0.78365(8) 0.94592(14) 0.0193(3) Uani 1 1 d . . . . . H11A H 0.630086 0.761730 0.902668 0.029 Uiso 1 1 calc R U . . . H11B H 0.500181 0.749200 0.981347 0.029 Uiso 1 1 calc R U . . . H11C H 0.609280 0.812215 1.017109 0.029 Uiso 1 1 calc R U . . . C12 C 0.19418(16) 0.46326(7) 0.74605(13) 0.0144(3) Uani 1 1 d . . . . . C13 C 0.27647(17) 0.40368(7) 0.75352(14) 0.0175(3) Uani 1 1 d . . . . . H13 H 0.353998 0.399717 0.706102 0.021 Uiso 1 1 calc R U . . . C14 C 0.24569(18) 0.35012(8) 0.82990(15) 0.0220(3) Uani 1 1 d . . . . . H14 H 0.301352 0.309588 0.833527 0.026 Uiso 1 1 calc R U . . . C15 C 0.1339(2) 0.35576(8) 0.90078(15) 0.0240(3) Uani 1 1 d . . . . . H15 H 0.112704 0.319157 0.952771 0.029 Uiso 1 1 calc R U . . . C16 C 0.05310(19) 0.41530(8) 0.89529(16) 0.0249(3) Uani 1 1 d . . . . . H16 H -0.022339 0.419574 0.944919 0.030 Uiso 1 1 calc R U . . . C17 C 0.08192(18) 0.46846(7) 0.81783(15) 0.0195(3) Uani 1 1 d . . . . . H17 H 0.024991 0.508646 0.813558 0.023 Uiso 1 1 calc R U . . . C18 C 0.24300(15) 0.46285(7) 0.44158(13) 0.0133(2) Uani 1 1 d . . . . . C19 C 0.13358(16) 0.41326(7) 0.43201(14) 0.0155(3) Uani 1 1 d . . . . . H19 H 0.065296 0.414483 0.489161 0.019 Uiso 1 1 calc R U . . . C20 C 0.12365(17) 0.36206(7) 0.33949(14) 0.0192(3) Uani 1 1 d . . . . . H20 H 0.048824 0.328573 0.333547 0.023 Uiso 1 1 calc R U . . . C21 C 0.22328(19) 0.36009(7) 0.25605(14) 0.0222(3) Uani 1 1 d . . . . . H21 H 0.216690 0.325218 0.192839 0.027 Uiso 1 1 calc R U . . . C22 C 0.33263(19) 0.40901(8) 0.26476(15) 0.0224(3) Uani 1 1 d . . . . . H22 H 0.400679 0.407430 0.207421 0.027 Uiso 1 1 calc R U . . . C23 C 0.34324(18) 0.46035(7) 0.35697(14) 0.0188(3) Uani 1 1 d . . . . . H23 H 0.418382 0.493658 0.362508 0.023 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 Br1 0.01574(7) 0.01485(6) 0.01429(7) -0.00058(5) -0.00189(5) -0.00127(5) O1 0.0274(6) 0.0104(4) 0.0188(5) -0.0014(4) 0.0020(4) -0.0018(4) O2 0.0202(5) 0.0156(5) 0.0130(5) -0.0029(4) -0.0007(4) -0.0028(4) N1 0.0169(6) 0.0123(5) 0.0125(5) 0.0006(4) 0.0046(4) -0.0009(4) N2 0.0142(5) 0.0129(5) 0.0134(5) -0.0007(4) 0.0020(4) -0.0012(4) C1 0.0130(6) 0.0131(6) 0.0125(6) -0.0013(5) 0.0004(5) -0.0003(5) C2 0.0127(6) 0.0127(6) 0.0133(6) -0.0008(5) 0.0018(5) -0.0004(5) C3 0.0135(6) 0.0117(6) 0.0136(6) 0.0004(4) 0.0024(5) -0.0010(5) C4 0.0134(6) 0.0119(6) 0.0137(6) -0.0009(4) 0.0045(5) -0.0002(5) C5 0.0126(6) 0.0140(6) 0.0121(6) -0.0024(5) 0.0002(5) -0.0010(5) C6 0.0156(6) 0.0135(6) 0.0140(6) 0.0005(5) 0.0022(5) 0.0018(5) C7 0.0162(7) 0.0101(6) 0.0162(6) -0.0021(5) 0.0048(5) -0.0007(5) C8 0.0140(6) 0.0143(6) 0.0123(6) -0.0026(5) 0.0029(5) -0.0022(5) C9 0.0149(6) 0.0135(6) 0.0122(6) 0.0002(4) 0.0021(5) -0.0001(5) C10 0.0473(11) 0.0156(7) 0.0250(8) 0.0026(6) 0.0059(7) -0.0089(7) C11 0.0180(7) 0.0233(7) 0.0149(7) -0.0012(5) -0.0010(5) -0.0018(6) C12 0.0173(7) 0.0138(6) 0.0112(6) -0.0006(5) 0.0009(5) -0.0033(5) C13 0.0188(7) 0.0171(6) 0.0156(7) 0.0020(5) 0.0011(5) 0.0013(5) C14 0.0266(8) 0.0171(7) 0.0191(7) 0.0049(5) -0.0030(6) -0.0003(6) C15 0.0362(9) 0.0205(7) 0.0136(7) 0.0040(5) 0.0008(6) -0.0108(6) C16 0.0313(9) 0.0257(8) 0.0203(8) -0.0017(6) 0.0118(7) -0.0097(6) C17 0.0234(8) 0.0177(7) 0.0191(7) -0.0020(5) 0.0082(6) -0.0032(6) C18 0.0159(6) 0.0120(6) 0.0113(6) 0.0008(4) 0.0009(5) 0.0029(5) C19 0.0150(6) 0.0155(6) 0.0153(6) -0.0012(5) 0.0012(5) 0.0008(5) C20 0.0199(7) 0.0157(6) 0.0190(7) -0.0025(5) -0.0036(6) 0.0004(5) C21 0.0346(9) 0.0176(7) 0.0122(6) -0.0023(5) -0.0003(6) 0.0075(6) C22 0.0330(9) 0.0202(7) 0.0160(7) 0.0014(5) 0.0100(6) 0.0071(6) C23 0.0241(8) 0.0161(6) 0.0176(7) 0.0022(5) 0.0071(6) 0.0020(5) _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 Br1 C5 1.9022(13) . ? O1 C7 1.3634(16) . ? O1 C10 1.4237(19) . ? O2 C8 1.3675(16) . ? O2 C11 1.4328(17) . ? N1 C1 1.3611(17) . ? N1 C3 1.3780(17) . ? N1 H1 0.85(2) . ? N2 C1 1.3220(18) . ? N2 C2 1.3839(17) . ? C1 C4 1.4716(18) . ? C2 C3 1.3835(19) . ? C2 C12 1.4714(19) . ? C3 C18 1.4700(18) . ? C4 C5 1.3896(18) . ? C4 C9 1.4073(18) . ? C5 C6 1.3960(18) . ? C6 C7 1.3838(19) . ? C6 H6 0.9500 . ? C7 C8 1.4093(19) . ? C8 C9 1.3807(18) . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C17 1.397(2) . ? C12 C13 1.397(2) . ? C13 C14 1.391(2) . ? C13 H13 0.9500 . ? C14 C15 1.387(2) . ? C14 H14 0.9500 . ? C15 C16 1.391(2) . ? C15 H15 0.9500 . ? C16 C17 1.387(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.3973(19) . ? C18 C23 1.401(2) . ? C19 C20 1.3925(19) . ? C19 H19 0.9500 . ? C20 C21 1.387(2) . ? C20 H20 0.9500 . ? C21 C22 1.388(2) . ? C21 H21 0.9500 . ? C22 C23 1.392(2) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? 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 C7 O1 C10 116.87(12) . . ? C8 O2 C11 117.14(11) . . ? C1 N1 C3 107.92(12) . . ? C1 N1 H1 125.0(13) . . ? C3 N1 H1 127.0(13) . . ? C1 N2 C2 105.44(11) . . ? N2 C1 N1 111.47(12) . . ? N2 C1 C4 124.27(12) . . ? N1 C1 C4 124.26(12) . . ? C3 C2 N2 110.25(12) . . ? C3 C2 C12 128.64(12) . . ? N2 C2 C12 121.11(12) . . ? N1 C3 C2 104.92(12) . . ? N1 C3 C18 122.22(12) . . ? C2 C3 C18 132.74(12) . . ? C5 C4 C9 117.99(12) . . ? C5 C4 C1 124.72(12) . . ? C9 C4 C1 117.28(12) . . ? C4 C5 C6 121.63(12) . . ? C4 C5 Br1 121.21(10) . . ? C6 C5 Br1 117.05(10) . . ? C7 C6 C5 119.51(12) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? O1 C7 C6 124.88(13) . . ? O1 C7 C8 115.29(12) . . ? C6 C7 C8 119.80(12) . . ? O2 C8 C9 124.90(12) . . ? O2 C8 C7 115.31(12) . . ? C9 C8 C7 119.78(12) . . ? C8 C9 C4 121.05(12) . . ? C8 C9 H9 119.5 . . ? C4 C9 H9 119.5 . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 118.92(13) . . ? C17 C12 C2 120.54(13) . . ? C13 C12 C2 120.54(13) . . ? C14 C13 C12 120.48(14) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 120.17(15) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.62(14) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 120.43(15) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C12 120.37(14) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? C19 C18 C23 119.10(13) . . ? C19 C18 C3 119.67(13) . . ? C23 C18 C3 121.19(13) . . ? C20 C19 C18 120.64(14) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C21 C20 C19 119.81(14) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 120.09(14) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C23 120.43(15) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C18 119.93(14) . . ? C22 C23 H23 120.0 . . ? C18 C23 H23 120.0 . . ? _refine_diff_density_max 0.457 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.069 _shelx_res_file ; TITL i18083_a.res in P2(1)/c i18083.res created by SHELXL-2018/3 at 14:29:04 on 22-Feb-2021 REM Old TITL i18083 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.070, Rweak 0.004, Alpha 0.063, Orientation as input REM Formula found by SHELXT: C23 N2 O2 Br CELL 0.71073 9.2089 19.8306 10.4519 90.000 101.492 90.000 ZERR 4.000 0.0002 0.0003 0.0002 0.000 0.001 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O BR UNIT 92 76 8 8 4 ACTA TEMP -173.150 SIZE 0.095 0.185 0.201 L.S. 10 BOND $H LIST 6 FMAP 2 PLAN 5 OMIT 1 1 0 WGHT 0.023100 1.262900 FVAR 0.43093 BR1 5 0.067138 0.709171 0.373146 11.00000 0.01574 0.01485 = 0.01429 -0.00058 -0.00189 -0.00127 O1 4 0.352953 0.902926 0.661124 11.00000 0.02742 0.01045 = 0.01880 -0.00137 0.00204 -0.00178 O2 4 0.459542 0.824298 0.853304 11.00000 0.02023 0.01557 = 0.01298 -0.00286 -0.00068 -0.00278 N1 3 0.270947 0.583941 0.506258 11.00000 0.01692 0.01228 = 0.01246 0.00058 0.00462 -0.00087 H1 2 0.292068 0.598793 0.435392 11.00000 0.02220 N2 3 0.232855 0.585271 0.709155 11.00000 0.01419 0.01287 = 0.01335 -0.00074 0.00204 -0.00125 C1 1 0.259180 0.622540 0.611395 11.00000 0.01295 0.01309 = 0.01251 -0.00126 0.00039 -0.00027 C2 1 0.225106 0.519554 0.663739 11.00000 0.01269 0.01274 = 0.01330 -0.00080 0.00178 -0.00035 C3 1 0.248213 0.517710 0.536982 11.00000 0.01350 0.01165 = 0.01363 0.00039 0.00237 -0.00104 C4 1 0.276283 0.696330 0.616435 11.00000 0.01341 0.01186 = 0.01373 -0.00093 0.00449 -0.00023 C5 1 0.208544 0.740369 0.519255 11.00000 0.01258 0.01397 = 0.01206 -0.00239 0.00021 -0.00095 C6 1 0.234427 0.809735 0.528227 11.00000 0.01558 0.01354 = 0.01402 0.00050 0.00220 0.00181 AFIX 43 H6 2 0.191923 0.838617 0.458222 11.00000 -1.20000 AFIX 0 C7 1 0.322455 0.836114 0.639847 11.00000 0.01621 0.01010 = 0.01623 -0.00207 0.00475 -0.00071 C8 1 0.384472 0.792871 0.743373 11.00000 0.01401 0.01434 = 0.01233 -0.00261 0.00290 -0.00218 C9 1 0.364717 0.724041 0.729605 11.00000 0.01490 0.01349 = 0.01221 0.00024 0.00207 -0.00010 AFIX 43 H9 2 0.411567 0.694927 0.797611 11.00000 -1.20000 AFIX 0 C10 1 0.348340 0.944136 0.548845 11.00000 0.04731 0.01560 = 0.02502 0.00261 0.00587 -0.00894 AFIX 137 H10A 2 0.402465 0.921890 0.488877 11.00000 -1.50000 H10B 2 0.394332 0.987826 0.575451 11.00000 -1.50000 H10C 2 0.245048 0.951060 0.504922 11.00000 -1.50000 AFIX 0 C11 1 0.557512 0.783649 0.945924 11.00000 0.01800 0.02325 = 0.01486 -0.00119 -0.00096 -0.00176 AFIX 137 H11A 2 0.630086 0.761730 0.902668 11.00000 -1.50000 H11B 2 0.500181 0.749200 0.981347 11.00000 -1.50000 H11C 2 0.609280 0.812215 1.017109 11.00000 -1.50000 AFIX 0 C12 1 0.194184 0.463261 0.746053 11.00000 0.01732 0.01382 = 0.01120 -0.00057 0.00090 -0.00329 C13 1 0.276472 0.403681 0.753521 11.00000 0.01877 0.01715 = 0.01560 0.00204 0.00107 0.00135 AFIX 43 H13 2 0.353998 0.399717 0.706102 11.00000 -1.20000 AFIX 0 C14 1 0.245688 0.350120 0.829904 11.00000 0.02662 0.01714 = 0.01907 0.00487 -0.00305 -0.00029 AFIX 43 H14 2 0.301352 0.309588 0.833527 11.00000 -1.20000 AFIX 0 C15 1 0.133918 0.355756 0.900782 11.00000 0.03624 0.02053 = 0.01364 0.00395 0.00083 -0.01078 AFIX 43 H15 2 0.112704 0.319157 0.952771 11.00000 -1.20000 AFIX 0 C16 1 0.053099 0.415298 0.895286 11.00000 0.03134 0.02570 = 0.02029 -0.00169 0.01184 -0.00974 AFIX 43 H16 2 -0.022339 0.419574 0.944919 11.00000 -1.20000 AFIX 0 C17 1 0.081917 0.468462 0.817831 11.00000 0.02342 0.01771 = 0.01914 -0.00200 0.00820 -0.00322 AFIX 43 H17 2 0.024991 0.508646 0.813558 11.00000 -1.20000 AFIX 0 C18 1 0.243003 0.462853 0.441584 11.00000 0.01592 0.01196 = 0.01127 0.00079 0.00090 0.00289 C19 1 0.133575 0.413259 0.432005 11.00000 0.01504 0.01548 = 0.01528 -0.00115 0.00121 0.00076 AFIX 43 H19 2 0.065296 0.414483 0.489161 11.00000 -1.20000 AFIX 0 C20 1 0.123645 0.362059 0.339485 11.00000 0.01990 0.01569 = 0.01896 -0.00250 -0.00356 0.00044 AFIX 43 H20 2 0.048824 0.328573 0.333547 11.00000 -1.20000 AFIX 0 C21 1 0.223278 0.360092 0.256053 11.00000 0.03463 0.01763 = 0.01220 -0.00228 -0.00031 0.00751 AFIX 43 H21 2 0.216690 0.325218 0.192839 11.00000 -1.20000 AFIX 0 C22 1 0.332633 0.409006 0.264764 11.00000 0.03299 0.02016 = 0.01603 0.00135 0.00999 0.00708 AFIX 43 H22 2 0.400679 0.407430 0.207421 11.00000 -1.20000 AFIX 0 C23 1 0.343240 0.460350 0.356971 11.00000 0.02405 0.01608 = 0.01761 0.00223 0.00705 0.00203 AFIX 43 H23 2 0.418382 0.493658 0.362508 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 REM i18083_a.res in P2(1)/c REM wR2 = 0.060258, GooF = S = 1.03620, Restrained GooF = 1.03620 for all data REM R1 = 0.026205 for 4848 Fo > 4sig(Fo) and 0.036596 for all 5710 data REM 259 parameters refined using 0 restraints END WGHT 0.0231 1.2621 REM Highest difference peak 0.457, deepest hole -0.365, 1-sigma level 0.069 Q1 1 0.2315 0.7737 0.5208 11.00000 0.05 0.46 Q2 1 0.2394 0.5106 0.6029 11.00000 0.05 0.42 Q3 1 0.2651 0.6600 0.6037 11.00000 0.05 0.40 Q4 1 0.3197 0.4411 0.3010 11.00000 0.05 0.39 Q5 1 0.2500 0.4872 0.4935 11.00000 0.05 0.38 ; _shelx_res_checksum 6016 ####################################################################### # # 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_i18117 _database_code_depnum_ccdc_archive 'CCDC 2082032' loop_ _audit_author_name _audit_author_address 'Kesatebrhan Haile Asressu' ;Academia Sinica Taiwan ; _audit_update_record ; 2021-05-06 deposited with the CCDC. 2021-08-12 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H28 N4 O2' _chemical_formula_sum 'C38 H28 N4 O2' _chemical_formula_weight 572.64 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' N N 0.0311 0.0180 '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' _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_H-M_alt 'P n a 21' _space_group_name_Hall 'P 2c -2n' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 8.9585(4) _cell_length_b 11.3947(5) _cell_length_c 28.7859(13) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2938.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 3336 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 62.85 _exptl_crystal_description niddle _exptl_crystal_colour colourless _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.294 _exptl_crystal_F_000 1200 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.060 _exptl_absorpt_coefficient_mu 0.644 _shelx_estimated_absorpt_T_min 0.820 _shelx_estimated_absorpt_T_max 0.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9329 _exptl_absorpt_correction_T_max 0.9621 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100.0(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27891 _diffrn_reflns_av_unetI/netI 0.1014 _diffrn_reflns_av_R_equivalents 0.1401 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.070 _diffrn_reflns_theta_max 66.595 _diffrn_reflns_theta_full 66.595 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_point_group_measured_fraction_full 0.987 _reflns_number_total 5125 _reflns_number_gt 3518 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.938 _reflns_Friedel_fraction_max 0.976 _reflns_Friedel_fraction_full 0.976 _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. ; _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 958)' _computing_publication_material 'WinGX publication routines (Farrugia, 2014)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1560P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 1214 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.1(4) _chemical_absolute_configuration ad _refine_ls_number_reflns 5125 _refine_ls_number_parameters 403 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1249 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.2411 _refine_ls_wR_factor_gt 0.2137 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.1603(7) 0.3907(5) 0.5150(2) 0.0362(15) Uani 1 1 d . . . . . O2 O 0.5472(7) 0.6077(5) 0.4919(2) 0.0404(16) Uani 1 1 d . . . . . N1 N 0.3283(8) 0.1445(6) 0.5762(2) 0.0279(16) Uani 1 1 d . . . . . N2 N 0.1123(9) 0.2322(6) 0.5888(3) 0.0278(16) Uani 1 1 d . . . . . H2 H 0.034(10) 0.282(8) 0.584(3) 0.033 Uiso 1 1 d . U . . . N3 N 0.3780(9) 0.8541(7) 0.4306(2) 0.0341(18) Uani 1 1 d . . . . . N4 N 0.5962(9) 0.7675(7) 0.4171(3) 0.0337(18) Uani 1 1 d . . . . . H4 H 0.679(12) 0.722(9) 0.419(4) 0.040 Uiso 1 1 d . U . . . C1 C 0.2351(10) 0.2299(8) 0.5627(3) 0.033(2) Uani 1 1 d . . . . . C2 C 0.2570(9) 0.0889(7) 0.6133(3) 0.0254(18) Uani 1 1 d . . . . . C3 C 0.1206(10) 0.1447(8) 0.6209(3) 0.0284(19) Uani 1 1 d . . . . . C4 C 0.2628(10) 0.3023(7) 0.5219(3) 0.031(2) Uani 1 1 d . . . . . C5 C 0.3612(11) 0.2976(9) 0.4877(3) 0.038(2) Uani 1 1 d . . . . . H5 H 0.441158 0.243442 0.484441 0.046 Uiso 1 1 calc R U . . . C6 C 0.3227(12) 0.3909(10) 0.4564(4) 0.046(3) Uani 1 1 d . . . . . H6 H 0.373392 0.411609 0.428622 0.055 Uiso 1 1 calc R U . . . C7 C 0.2011(11) 0.4432(9) 0.4741(4) 0.042(2) Uani 1 1 d . . . . . H7 H 0.150509 0.507504 0.460168 0.051 Uiso 1 1 calc R U . . . C8 C 0.3310(10) -0.0078(7) 0.6384(3) 0.031(2) Uani 1 1 d . . . . . C9 C 0.4331(10) -0.0788(8) 0.6145(3) 0.034(2) Uani 1 1 d . . . . . H9 H 0.454334 -0.064115 0.582723 0.041 Uiso 1 1 calc R U . . . C10 C 0.5026(10) -0.1699(8) 0.6372(3) 0.036(2) Uani 1 1 d . . . . . H10 H 0.570165 -0.218729 0.620664 0.043 Uiso 1 1 calc R U . . . C11 C 0.4757(11) -0.1918(8) 0.6840(4) 0.042(2) Uani 1 1 d . . . . . H11 H 0.525317 -0.254115 0.699499 0.051 Uiso 1 1 calc R U . . . C12 C 0.3749(11) -0.1208(8) 0.7076(4) 0.040(2) Uani 1 1 d . . . . . H12 H 0.355532 -0.134798 0.739557 0.048 Uiso 1 1 calc R U . . . C13 C 0.3035(11) -0.0311(8) 0.6852(3) 0.031(2) Uani 1 1 d . . . . . H13 H 0.234096 0.015989 0.701829 0.038 Uiso 1 1 calc R U . . . C14 C -0.0041(9) 0.1206(8) 0.6522(3) 0.0287(19) Uani 1 1 d . . . . . C15 C -0.0585(10) 0.0058(8) 0.6587(4) 0.033(2) Uani 1 1 d . . . . . H15 H -0.010220 -0.057905 0.643695 0.040 Uiso 1 1 calc R U . . . C16 C -0.1799(10) -0.0154(9) 0.6864(3) 0.035(2) Uani 1 1 d . . . . . H16 H -0.212003 -0.093805 0.691593 0.042 Uiso 1 1 calc R U . . . C17 C -0.2559(11) 0.0768(8) 0.7068(4) 0.041(2) Uani 1 1 d . . . . . H17 H -0.344357 0.062232 0.724039 0.049 Uiso 1 1 calc R U . . . C18 C -0.2030(10) 0.1905(8) 0.7021(3) 0.034(2) Uani 1 1 d . . . . . H18 H -0.251354 0.253277 0.717769 0.040 Uiso 1 1 calc R U . . . C19 C -0.0789(9) 0.2123(8) 0.6744(3) 0.0293(19) Uani 1 1 d . . . . . H19 H -0.044577 0.290546 0.670602 0.035 Uiso 1 1 calc R U . . . C20 C 0.4720(10) 0.7714(7) 0.4443(3) 0.0294(19) Uani 1 1 d . . . . . C21 C 0.4469(10) 0.9092(7) 0.3940(3) 0.030(2) Uani 1 1 d . . . . . C22 C 0.5837(9) 0.8569(7) 0.3850(3) 0.0283(19) Uani 1 1 d . . . . . C23 C 0.4481(10) 0.6968(8) 0.4840(3) 0.033(2) Uani 1 1 d . . . . . C24 C 0.3439(11) 0.6995(9) 0.5188(3) 0.039(2) Uani 1 1 d . . . . . H24 H 0.261734 0.751784 0.521284 0.047 Uiso 1 1 calc R U . . . C25 C 0.3831(12) 0.6079(10) 0.5505(4) 0.046(3) Uani 1 1 d . . . . . H25 H 0.334121 0.588892 0.578813 0.055 Uiso 1 1 calc R U . . . C26 C 0.5028(12) 0.5545(8) 0.5324(3) 0.039(2) Uani 1 1 d . . . . . H26 H 0.550811 0.488354 0.545766 0.047 Uiso 1 1 calc R U . . . C27 C 0.3673(10) 1.0069(8) 0.3712(3) 0.032(2) Uani 1 1 d . . . . . C28 C 0.2642(11) 1.0714(8) 0.3959(4) 0.038(2) Uani 1 1 d . . . . . H28 H 0.248434 1.052784 0.427687 0.046 Uiso 1 1 calc R U . . . C29 C 0.1827(11) 1.1622(8) 0.3764(3) 0.041(2) Uani 1 1 d . . . . . H29 H 0.112788 1.205459 0.394365 0.049 Uiso 1 1 calc R U . . . C30 C 0.2067(11) 1.1889(9) 0.3286(3) 0.039(2) Uani 1 1 d . . . . . H30 H 0.150885 1.249584 0.314121 0.047 Uiso 1 1 calc R U . . . C31 C 0.3109(10) 1.1268(8) 0.3036(3) 0.032(2) Uani 1 1 d . . . . . H31 H 0.328650 1.145769 0.271898 0.039 Uiso 1 1 calc R U . . . C32 C 0.3911(11) 1.0352(8) 0.3247(3) 0.032(2) Uani 1 1 d . . . . . H32 H 0.462297 0.992250 0.307155 0.039 Uiso 1 1 calc R U . . . C33 C 0.7041(10) 0.8817(8) 0.3516(3) 0.031(2) Uani 1 1 d . . . . . C34 C 0.7492(10) 0.9985(8) 0.3427(3) 0.034(2) Uani 1 1 d . . . . . H34 H 0.698257 1.062043 0.356967 0.040 Uiso 1 1 calc R U . . . C35 C 0.8664(11) 1.0196(9) 0.3134(3) 0.036(2) Uani 1 1 d . . . . . H35 H 0.895321 1.098286 0.307179 0.043 Uiso 1 1 calc R U . . . C36 C 0.9441(11) 0.9280(9) 0.2925(3) 0.041(2) Uani 1 1 d . . . . . H36 H 1.026634 0.943394 0.272672 0.049 Uiso 1 1 calc R U . . . C37 C 0.8983(11) 0.8128(8) 0.3011(3) 0.035(2) Uani 1 1 d . . . . . H37 H 0.949962 0.749466 0.286954 0.042 Uiso 1 1 calc R U . . . C38 C 0.7807(10) 0.7904(8) 0.3296(3) 0.035(2) Uani 1 1 d . . . . . H38 H 0.750170 0.711579 0.334707 0.042 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 0.033(3) 0.034(3) 0.041(4) 0.013(3) -0.002(3) 0.002(3) O2 0.046(4) 0.036(4) 0.040(4) 0.007(3) 0.000(3) -0.002(3) N1 0.030(4) 0.025(4) 0.029(4) 0.007(3) -0.002(3) 0.001(3) N2 0.030(4) 0.022(4) 0.031(4) 0.004(3) -0.001(3) 0.003(3) N3 0.038(5) 0.033(4) 0.032(4) 0.000(3) -0.001(3) -0.008(3) N4 0.042(5) 0.029(4) 0.031(4) -0.004(3) -0.003(4) -0.003(3) C1 0.037(5) 0.027(5) 0.034(5) 0.009(4) -0.003(4) -0.007(4) C2 0.018(4) 0.029(4) 0.029(5) 0.002(4) -0.005(3) -0.004(3) C3 0.035(5) 0.027(4) 0.024(4) -0.003(4) 0.000(4) -0.003(4) C4 0.036(5) 0.026(5) 0.031(5) 0.006(4) -0.002(4) 0.002(4) C5 0.041(5) 0.041(6) 0.032(5) 0.003(4) 0.011(4) 0.000(4) C6 0.047(6) 0.053(6) 0.037(5) 0.017(5) -0.006(5) -0.010(5) C7 0.040(6) 0.039(6) 0.048(6) 0.021(5) -0.002(5) -0.004(4) C8 0.029(5) 0.023(5) 0.041(5) 0.005(4) -0.001(4) -0.007(3) C9 0.036(5) 0.028(5) 0.038(5) -0.002(4) 0.003(4) 0.003(4) C10 0.033(5) 0.031(5) 0.045(6) -0.009(4) -0.007(4) 0.010(4) C11 0.041(5) 0.031(5) 0.055(6) 0.002(5) -0.021(5) -0.002(4) C12 0.047(6) 0.032(5) 0.041(5) -0.001(4) -0.011(4) 0.002(4) C13 0.039(5) 0.030(5) 0.026(5) -0.002(4) 0.000(4) -0.004(4) C14 0.025(4) 0.031(5) 0.030(5) -0.005(4) -0.011(4) 0.001(4) C15 0.034(5) 0.025(5) 0.040(5) 0.004(4) 0.010(4) 0.001(4) C16 0.032(5) 0.037(5) 0.035(5) 0.005(4) -0.005(4) -0.006(4) C17 0.031(5) 0.042(6) 0.050(6) 0.014(5) 0.003(4) 0.001(4) C18 0.036(5) 0.036(5) 0.029(5) 0.000(4) -0.006(4) 0.012(4) C19 0.026(4) 0.033(5) 0.029(5) 0.005(4) -0.008(4) 0.002(3) C20 0.033(5) 0.025(4) 0.030(5) -0.004(4) -0.004(4) -0.003(4) C21 0.037(5) 0.028(5) 0.025(4) -0.006(4) -0.003(4) 0.001(4) C22 0.031(5) 0.024(4) 0.030(5) -0.004(4) 0.000(4) -0.002(3) C23 0.034(5) 0.033(5) 0.031(5) 0.006(4) -0.005(4) 0.002(4) C24 0.045(6) 0.040(5) 0.032(5) 0.003(5) -0.003(4) -0.002(4) C25 0.049(6) 0.053(6) 0.036(5) 0.004(5) 0.000(5) -0.014(5) C26 0.048(6) 0.036(5) 0.034(5) 0.010(4) -0.002(5) -0.009(5) C27 0.030(5) 0.025(5) 0.040(5) -0.004(4) 0.005(4) -0.004(4) C28 0.039(6) 0.038(5) 0.037(5) 0.003(4) 0.003(4) -0.002(4) C29 0.044(6) 0.036(5) 0.043(6) 0.010(4) -0.001(5) 0.005(4) C30 0.040(5) 0.039(5) 0.039(5) 0.001(4) -0.004(4) 0.002(4) C31 0.044(5) 0.029(5) 0.024(4) 0.005(4) 0.001(4) -0.003(4) C32 0.041(5) 0.022(4) 0.034(5) -0.001(4) -0.005(4) -0.002(4) C33 0.034(5) 0.030(5) 0.029(5) 0.004(4) 0.003(4) -0.002(4) C34 0.034(5) 0.038(5) 0.030(5) -0.008(4) -0.009(4) -0.002(4) C35 0.045(6) 0.031(5) 0.033(5) 0.011(4) -0.006(4) -0.011(4) C36 0.039(6) 0.049(6) 0.035(5) 0.001(5) 0.001(4) -0.005(4) C37 0.038(5) 0.038(5) 0.030(5) -0.005(4) 0.002(4) 0.007(4) C38 0.047(6) 0.028(5) 0.031(5) -0.003(4) -0.001(4) 0.006(4) _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 1.371(12) . ? O1 C4 1.377(10) . ? O2 C23 1.368(11) . ? O2 C26 1.372(11) . ? N1 C1 1.339(11) . ? N1 C2 1.398(11) . ? N2 C1 1.332(12) . ? N2 C3 1.361(12) . ? N2 H2 0.91(10) . ? N3 C20 1.324(12) . ? N3 C21 1.374(11) . ? N4 C20 1.362(12) . ? N4 C22 1.380(12) . ? N4 H4 0.90(11) . ? C1 C4 1.458(12) . ? C2 C3 1.395(12) . ? C2 C8 1.474(12) . ? C3 C14 1.461(12) . ? C4 C5 1.323(13) . ? C5 C6 1.435(15) . ? C5 H5 0.9500 . ? C6 C7 1.341(15) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.397(12) . ? C8 C9 1.402(13) . ? C9 C10 1.375(12) . ? C9 H9 0.9500 . ? C10 C11 1.389(14) . ? C10 H10 0.9500 . ? C11 C12 1.390(14) . ? C11 H11 0.9500 . ? C12 C13 1.367(13) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.397(12) . ? C14 C15 1.408(12) . ? C15 C16 1.369(13) . ? C15 H15 0.9500 . ? C16 C17 1.383(14) . ? C16 H16 0.9500 . ? C17 C18 1.386(13) . ? C17 H17 0.9500 . ? C18 C19 1.390(12) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C23 1.441(13) . ? C21 C22 1.387(12) . ? C21 C27 1.476(13) . ? C22 C33 1.473(12) . ? C23 C24 1.368(14) . ? C24 C25 1.431(15) . ? C24 H24 0.9500 . ? C25 C26 1.339(15) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.378(13) . ? C27 C32 1.392(13) . ? C28 C29 1.386(13) . ? C28 H28 0.9500 . ? C29 C30 1.424(14) . ? C29 H29 0.9500 . ? C30 C31 1.376(13) . ? C30 H30 0.9500 . ? C31 C32 1.406(13) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C38 1.397(12) . ? C33 C34 1.414(12) . ? C34 C35 1.368(13) . ? C34 H34 0.9500 . ? C35 C36 1.392(14) . ? C35 H35 0.9500 . ? C36 C37 1.397(14) . ? C36 H36 0.9500 . ? C37 C38 1.360(13) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? 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 C7 O1 C4 105.4(7) . . ? C23 O2 C26 106.3(7) . . ? C1 N1 C2 105.4(7) . . ? C1 N2 C3 108.8(8) . . ? C1 N2 H2 125(6) . . ? C3 N2 H2 126(6) . . ? C20 N3 C21 105.6(8) . . ? C20 N4 C22 107.2(8) . . ? C20 N4 H4 130(7) . . ? C22 N4 H4 122(7) . . ? N2 C1 N1 111.5(8) . . ? N2 C1 C4 125.7(8) . . ? N1 C1 C4 122.6(8) . . ? C3 C2 N1 108.2(7) . . ? C3 C2 C8 131.2(8) . . ? N1 C2 C8 120.6(7) . . ? N2 C3 C2 106.1(8) . . ? N2 C3 C14 120.9(8) . . ? C2 C3 C14 132.8(8) . . ? C5 C4 O1 111.5(8) . . ? C5 C4 C1 133.7(9) . . ? O1 C4 C1 114.7(8) . . ? C4 C5 C6 106.0(9) . . ? C4 C5 H5 127.0 . . ? C6 C5 H5 127.0 . . ? C7 C6 C5 106.7(9) . . ? C7 C6 H6 126.7 . . ? C5 C6 H6 126.7 . . ? C6 C7 O1 110.4(9) . . ? C6 C7 H7 124.8 . . ? O1 C7 H7 124.8 . . ? C13 C8 C9 118.6(8) . . ? C13 C8 C2 122.4(8) . . ? C9 C8 C2 119.0(8) . . ? C10 C9 C8 119.9(9) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 121.1(9) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C12 118.9(9) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C13 C12 C11 120.6(9) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C8 121.0(9) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C19 C14 C15 117.8(8) . . ? C19 C14 C3 120.6(8) . . ? C15 C14 C3 121.5(8) . . ? C16 C15 C14 121.2(9) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 120.2(9) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 120.1(9) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 119.7(9) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C14 120.9(8) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? N3 C20 N4 111.8(8) . . ? N3 C20 C23 124.2(8) . . ? N4 C20 C23 124.0(8) . . ? N3 C21 C22 110.1(8) . . ? N3 C21 C27 118.0(8) . . ? C22 C21 C27 131.9(8) . . ? N4 C22 C21 105.3(8) . . ? N4 C22 C33 121.3(8) . . ? C21 C22 C33 133.4(8) . . ? O2 C23 C24 109.8(8) . . ? O2 C23 C20 118.2(8) . . ? C24 C23 C20 131.9(9) . . ? C23 C24 C25 106.5(9) . . ? C23 C24 H24 126.8 . . ? C25 C24 H24 126.8 . . ? C26 C25 C24 106.1(9) . . ? C26 C25 H25 126.9 . . ? C24 C25 H25 126.9 . . ? C25 C26 O2 111.3(9) . . ? C25 C26 H26 124.3 . . ? O2 C26 H26 124.3 . . ? C28 C27 C32 118.4(9) . . ? C28 C27 C21 119.7(8) . . ? C32 C27 C21 121.9(8) . . ? C27 C28 C29 122.8(9) . . ? C27 C28 H28 118.6 . . ? C29 C28 H28 118.6 . . ? C28 C29 C30 118.1(9) . . ? C28 C29 H29 121.0 . . ? C30 C29 H29 121.0 . . ? C31 C30 C29 119.9(9) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C32 120.1(8) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C27 C32 C31 120.7(9) . . ? C27 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C38 C33 C34 118.6(8) . . ? C38 C33 C22 120.8(8) . . ? C34 C33 C22 120.5(8) . . ? C35 C34 C33 119.8(9) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C34 C35 C36 121.2(9) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C35 C36 C37 118.7(9) . . ? C35 C36 H36 120.6 . . ? C37 C36 H36 120.6 . . ? C38 C37 C36 120.8(9) . . ? C38 C37 H37 119.6 . . ? C36 C37 H37 119.6 . . ? C37 C38 C33 120.8(8) . . ? C37 C38 H38 119.6 . . ? C33 C38 H38 119.6 . . ? _refine_diff_density_max 0.550 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.089 _shelx_res_file ; TITL i18117_a.res in Pna2(1) i18117.res created by SHELXL-2018/3 at 11:19:05 on 25-Feb-2021 REM Old TITL i18117 in P2(1)2(1)2(1) REM SHELXT solution in Pna2(1) REM R1 0.139, Rweak 0.024, Alpha 0.013, Orientation as input REM Flack x = 0.267 ( 0.337 ) from Parsons' quotients REM Formula found by SHELXT: C37 N4 O3 CELL 1.54178 8.9585 11.3947 28.7859 90.000 90.000 90.000 ZERR 4.000 0.0004 0.0005 0.0013 0.000 0.000 0.000 LATT -1 SYMM -X, -Y, 1/2+Z SYMM 1/2+X, 1/2-Y, Z SYMM 1/2-X, 1/2+Y, 1/2+Z SFAC C H N O UNIT 152 112 16 8 ACTA TEMP -173.150 SIZE 0.06 0.09 0.32 L.S. 10 BOND $H LIST 6 FMAP 2 PLAN 5 REM ##### WGHT 0.156000 FVAR 0.45253 O1 4 0.160260 0.390691 0.514967 11.00000 0.03312 0.03392 = 0.04145 0.01335 -0.00189 0.00177 O2 4 0.547206 0.607673 0.491881 11.00000 0.04583 0.03577 = 0.03957 0.00689 -0.00023 -0.00209 N1 3 0.328279 0.144543 0.576191 11.00000 0.03036 0.02465 = 0.02860 0.00676 -0.00161 0.00082 N2 3 0.112253 0.232191 0.588788 11.00000 0.02979 0.02205 = 0.03149 0.00352 -0.00147 0.00259 H2 2 0.033714 0.281804 0.584279 11.00000 -1.20000 N3 3 0.378011 0.854071 0.430594 11.00000 0.03763 0.03285 = 0.03177 -0.00010 -0.00052 -0.00773 N4 3 0.596162 0.767517 0.417055 11.00000 0.04162 0.02873 = 0.03062 -0.00351 -0.00324 -0.00311 H4 2 0.678850 0.722393 0.419282 11.00000 -1.20000 C1 1 0.235086 0.229935 0.562746 11.00000 0.03731 0.02730 = 0.03431 0.00911 -0.00315 -0.00725 C2 1 0.257033 0.088899 0.613345 11.00000 0.01789 0.02948 = 0.02893 0.00158 -0.00476 -0.00374 C3 1 0.120625 0.144723 0.620883 11.00000 0.03466 0.02653 = 0.02401 -0.00251 -0.00040 -0.00332 C4 1 0.262801 0.302347 0.521908 11.00000 0.03587 0.02609 = 0.03062 0.00618 -0.00164 0.00202 C5 1 0.361217 0.297611 0.487669 11.00000 0.04087 0.04068 = 0.03241 0.00343 0.01102 -0.00047 AFIX 43 H5 2 0.441158 0.243442 0.484441 11.00000 -1.20000 AFIX 0 C6 1 0.322660 0.390898 0.456419 11.00000 0.04724 0.05278 = 0.03740 0.01712 -0.00579 -0.00999 AFIX 43 H6 2 0.373392 0.411609 0.428622 11.00000 -1.20000 AFIX 0 C7 1 0.201118 0.443189 0.474059 11.00000 0.04007 0.03894 = 0.04816 0.02059 -0.00196 -0.00382 AFIX 43 H7 2 0.150509 0.507504 0.460168 11.00000 -1.20000 AFIX 0 C8 1 0.330959 -0.007761 0.638398 11.00000 0.02916 0.02345 = 0.04112 0.00490 -0.00079 -0.00676 C9 1 0.433136 -0.078848 0.614529 11.00000 0.03628 0.02845 = 0.03768 -0.00179 0.00318 0.00310 AFIX 43 H9 2 0.454334 -0.064115 0.582723 11.00000 -1.20000 AFIX 0 C10 1 0.502624 -0.169929 0.637223 11.00000 0.03265 0.03100 = 0.04504 -0.00863 -0.00716 0.00962 AFIX 43 H10 2 0.570165 -0.218729 0.620664 11.00000 -1.20000 AFIX 0 C11 1 0.475694 -0.191761 0.683961 11.00000 0.04108 0.03133 = 0.05468 0.00226 -0.02092 -0.00182 AFIX 43 H11 2 0.525317 -0.254115 0.699499 11.00000 -1.20000 AFIX 0 C12 1 0.374929 -0.120826 0.707587 11.00000 0.04679 0.03203 = 0.04128 -0.00070 -0.01068 0.00173 AFIX 43 H12 2 0.355532 -0.134798 0.739557 11.00000 -1.20000 AFIX 0 C13 1 0.303474 -0.031139 0.685247 11.00000 0.03851 0.03043 = 0.02550 -0.00210 0.00038 -0.00384 AFIX 43 H13 2 0.234096 0.015989 0.701829 11.00000 -1.20000 AFIX 0 C14 1 -0.004074 0.120620 0.652190 11.00000 0.02489 0.03123 = 0.03006 -0.00469 -0.01138 0.00108 C15 1 -0.058530 0.005849 0.658735 11.00000 0.03394 0.02541 = 0.03997 0.00398 0.01016 0.00131 AFIX 43 H15 2 -0.010220 -0.057905 0.643695 11.00000 -1.20000 AFIX 0 C16 1 -0.179887 -0.015439 0.686398 11.00000 0.03216 0.03720 = 0.03501 0.00512 -0.00516 -0.00577 AFIX 43 H16 2 -0.212003 -0.093805 0.691593 11.00000 -1.20000 AFIX 0 C17 1 -0.255852 0.076815 0.706800 11.00000 0.03096 0.04222 = 0.04998 0.01391 0.00326 0.00143 AFIX 43 H17 2 -0.344357 0.062232 0.724039 11.00000 -1.20000 AFIX 0 C18 1 -0.202993 0.190488 0.702121 11.00000 0.03581 0.03620 = 0.02898 0.00036 -0.00604 0.01201 AFIX 43 H18 2 -0.251354 0.253277 0.717769 11.00000 -1.20000 AFIX 0 C19 1 -0.078922 0.212266 0.674439 11.00000 0.02577 0.03306 = 0.02903 0.00528 -0.00777 0.00170 AFIX 43 H19 2 -0.044577 0.290546 0.670602 11.00000 -1.20000 AFIX 0 C20 1 0.472016 0.771381 0.444305 11.00000 0.03269 0.02531 = 0.03019 -0.00383 -0.00398 -0.00266 C21 1 0.446905 0.909227 0.393976 11.00000 0.03663 0.02809 = 0.02467 -0.00592 -0.00286 0.00138 C22 1 0.583667 0.856945 0.384977 11.00000 0.03123 0.02363 = 0.02998 -0.00355 0.00024 -0.00196 C23 1 0.448135 0.696821 0.484038 11.00000 0.03401 0.03284 = 0.03077 0.00571 -0.00515 0.00211 C24 1 0.343917 0.699481 0.518761 11.00000 0.04543 0.03968 = 0.03210 0.00310 -0.00348 -0.00175 AFIX 43 H24 2 0.261734 0.751784 0.521284 11.00000 -1.20000 AFIX 0 C25 1 0.383115 0.607941 0.550533 11.00000 0.04921 0.05306 = 0.03590 0.00371 0.00017 -0.01397 AFIX 43 H25 2 0.334121 0.588892 0.578813 11.00000 -1.20000 AFIX 0 C26 1 0.502817 0.554530 0.532355 11.00000 0.04804 0.03621 = 0.03391 0.00986 -0.00161 -0.00946 AFIX 43 H26 2 0.550811 0.488354 0.545766 11.00000 -1.20000 AFIX 0 C27 1 0.367285 1.006860 0.371165 11.00000 0.03015 0.02517 = 0.04028 -0.00357 0.00507 -0.00370 C28 1 0.264242 1.071390 0.395896 11.00000 0.03921 0.03835 = 0.03689 0.00312 0.00323 -0.00156 AFIX 43 H28 2 0.248434 1.052784 0.427687 11.00000 -1.20000 AFIX 0 C29 1 0.182705 1.162230 0.376396 11.00000 0.04439 0.03628 = 0.04301 0.00966 -0.00051 0.00484 AFIX 43 H29 2 0.112788 1.205459 0.394365 11.00000 -1.20000 AFIX 0 C30 1 0.206720 1.188936 0.328642 11.00000 0.03954 0.03858 = 0.03911 0.00087 -0.00352 0.00223 AFIX 43 H30 2 0.150885 1.249584 0.314121 11.00000 -1.20000 AFIX 0 C31 1 0.310911 1.126777 0.303555 11.00000 0.04354 0.02944 = 0.02394 0.00501 0.00097 -0.00344 AFIX 43 H31 2 0.328650 1.145769 0.271898 11.00000 -1.20000 AFIX 0 C32 1 0.391098 1.035220 0.324729 11.00000 0.04136 0.02211 = 0.03351 -0.00097 -0.00517 -0.00237 AFIX 43 H32 2 0.462297 0.992250 0.307155 11.00000 -1.20000 AFIX 0 C33 1 0.704144 0.881740 0.351569 11.00000 0.03440 0.02958 = 0.02903 0.00374 0.00306 -0.00190 C34 1 0.749196 0.998476 0.342661 11.00000 0.03350 0.03756 = 0.02991 -0.00773 -0.00877 -0.00175 AFIX 43 H34 2 0.698257 1.062043 0.356967 11.00000 -1.20000 AFIX 0 C35 1 0.866415 1.019608 0.313365 11.00000 0.04464 0.03110 = 0.03252 0.01122 -0.00560 -0.01095 AFIX 43 H35 2 0.895321 1.098286 0.307179 11.00000 -1.20000 AFIX 0 C36 1 0.944073 0.927963 0.292462 11.00000 0.03875 0.04862 = 0.03547 0.00059 0.00123 -0.00526 AFIX 43 H36 2 1.026634 0.943394 0.272672 11.00000 -1.20000 AFIX 0 C37 1 0.898292 0.812841 0.301140 11.00000 0.03756 0.03779 = 0.02998 -0.00488 0.00235 0.00657 AFIX 43 H37 2 0.949962 0.749466 0.286954 11.00000 -1.20000 AFIX 0 C38 1 0.780692 0.790390 0.329639 11.00000 0.04651 0.02835 = 0.03131 -0.00323 -0.00073 0.00566 AFIX 43 H38 2 0.750170 0.711579 0.334707 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 REM i18117_a.res in Pna2(1) REM wR2 = 0.241076, GooF = S = 1.01673, Restrained GooF = 1.01662 for all data REM R1 = 0.087106 for 3518 Fo > 4sig(Fo) and 0.124856 for all 5125 data REM 403 parameters refined using 1 restraints END WGHT 0.1556 0.0000 REM Highest difference peak 0.550, deepest hole -0.323, 1-sigma level 0.089 Q1 1 0.5427 -0.0005 0.6606 11.00000 0.05 0.55 Q2 1 0.9748 1.0273 0.3276 11.00000 0.05 0.55 Q3 1 0.7768 0.6185 0.3509 11.00000 0.05 0.54 Q4 1 0.6682 0.6409 0.3844 11.00000 0.05 0.51 Q5 1 0.1431 0.6138 0.4929 11.00000 0.05 0.51 ; _shelx_res_checksum 92527 ####################################################################### # # 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_i18108 _database_code_depnum_ccdc_archive 'CCDC 2082029' loop_ _audit_author_name _audit_author_address 'Kesatebrhan Haile Asressu' ;Academia Sinica Taiwan ; _audit_update_record ; 2021-05-06 deposited with the CCDC. 2021-08-12 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C23 H20 N2 O2), C H Cl3' _chemical_formula_sum 'C47 H41 Cl3 N4 O4' _chemical_formula_weight 832.19 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _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. ; 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' _cell_length_a 10.2370(4) _cell_length_b 18.3683(6) _cell_length_c 22.3540(8) _cell_angle_alpha 90 _cell_angle_beta 95.8070(10) _cell_angle_gamma 90 _cell_volume 4181.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 9505 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26.98 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.322 _exptl_crystal_F_000 1736 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.216 _exptl_crystal_size_mid 0.155 _exptl_crystal_size_min 0.040 _exptl_absorpt_coefficient_mu 0.269 _shelx_estimated_absorpt_T_min 0.944 _shelx_estimated_absorpt_T_max 0.989 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9646 _exptl_absorpt_correction_T_max 0.9971 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 167934 _diffrn_reflns_av_unetI/netI 0.0337 _diffrn_reflns_av_R_equivalents 0.1039 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.141 _diffrn_reflns_theta_max 27.103 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 9215 _reflns_number_gt 7022 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _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. ; _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 958)' _computing_publication_material 'WinGX publication routines (Farrugia, 2014)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0969P)^2^+7.4717P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 9215 _refine_ls_number_parameters 535 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1928 _refine_ls_wR_factor_gt 0.1759 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.74956(11) 0.36009(6) 0.41472(4) 0.0496(3) Uani 1 1 d . . . . . Cl2 Cl 0.82348(12) 0.49664(6) 0.47161(5) 0.0547(3) Uani 1 1 d . . . . . Cl3 Cl 0.82071(12) 0.36653(6) 0.54311(5) 0.0567(3) Uani 1 1 d . . . . . O1 O 0.12932(18) 0.70332(10) 0.72399(9) 0.0181(4) Uani 1 1 d . . . . . O2 O 0.24107(18) 0.89612(10) 0.60556(8) 0.0182(4) Uani 1 1 d . . . . . O3 O 0.5272(2) 0.44947(11) 0.56602(9) 0.0262(5) Uani 1 1 d . . . . . O4 O 0.6993(2) 0.68146(10) 0.60279(9) 0.0200(4) Uani 1 1 d . . . . . N1 N 0.6568(2) 0.86391(12) 0.76643(10) 0.0115(4) Uani 1 1 d . . . . . N2 N 0.6260(2) 0.74970(11) 0.79270(9) 0.0117(4) Uani 1 1 d . . . . . N3 N 0.5151(2) 0.60796(12) 0.80712(10) 0.0115(4) Uani 1 1 d . . . . . N4 N 0.4032(2) 0.50806(11) 0.78090(10) 0.0120(4) Uani 1 1 d . . . . . C1 C 0.5714(2) 0.80733(13) 0.76432(11) 0.0115(5) Uani 1 1 d . . . . . C2 C 0.7732(2) 0.84178(13) 0.79797(11) 0.0122(5) Uani 1 1 d . . . . . C3 C 0.7524(2) 0.77055(13) 0.81392(11) 0.0124(5) Uani 1 1 d . . . . . C4 C 0.4389(2) 0.80740(13) 0.73202(11) 0.0115(5) Uani 1 1 d . . . . . C5 C 0.3481(2) 0.75565(13) 0.74751(11) 0.0130(5) Uani 1 1 d . . . . . H5 H 0.368804 0.723856 0.780630 0.016 Uiso 1 1 calc R U . . . C6 C 0.2261(2) 0.75152(13) 0.71336(12) 0.0141(5) Uani 1 1 d . . . . . C7 C 0.1945(2) 0.79814(13) 0.66560(12) 0.0140(5) Uani 1 1 d . . . . . H7 H 0.112227 0.793832 0.642046 0.017 Uiso 1 1 calc R U . . . C8 C 0.2835(2) 0.85137(13) 0.65216(11) 0.0135(5) Uani 1 1 d . . . . . C9 C 0.4072(2) 0.85628(13) 0.68456(12) 0.0138(5) Uani 1 1 d . . . . . H9 H 0.468545 0.891996 0.674657 0.017 Uiso 1 1 calc R U . . . C10 C 0.1587(3) 0.65159(15) 0.77140(14) 0.0224(6) Uani 1 1 d . . . . . H10A H 0.083579 0.618937 0.773441 0.034 Uiso 1 1 calc R U . . . H10B H 0.176657 0.677355 0.809734 0.034 Uiso 1 1 calc R U . . . H10C H 0.236006 0.623074 0.763446 0.034 Uiso 1 1 calc R U . . . C11 C 0.3269(3) 0.95426(15) 0.59226(14) 0.0225(6) Uani 1 1 d . . . . . H11A H 0.409223 0.933990 0.580666 0.034 Uiso 1 1 calc R U . . . H11B H 0.345444 0.985025 0.627933 0.034 Uiso 1 1 calc R U . . . H11C H 0.284712 0.983541 0.559103 0.034 Uiso 1 1 calc R U . . . C12 C 0.8893(2) 0.88907(14) 0.80675(11) 0.0132(5) Uani 1 1 d . . . . . C13 C 0.8789(3) 0.96158(14) 0.82506(12) 0.0162(5) Uani 1 1 d . . . . . H13 H 0.796491 0.980015 0.834133 0.019 Uiso 1 1 calc R U . . . C14 C 0.9883(3) 1.00668(15) 0.83003(13) 0.0206(6) Uani 1 1 d . . . . . H14 H 0.980374 1.055732 0.842644 0.025 Uiso 1 1 calc R U . . . C15 C 1.1089(3) 0.98060(15) 0.81673(13) 0.0220(6) Uani 1 1 d . . . . . H15 H 1.183331 1.011737 0.819798 0.026 Uiso 1 1 calc R U . . . C16 C 1.1204(3) 0.90851(15) 0.79883(13) 0.0198(6) Uani 1 1 d . . . . . H16 H 1.203235 0.890284 0.790052 0.024 Uiso 1 1 calc R U . . . C17 C 1.0119(3) 0.86334(14) 0.79379(12) 0.0160(5) Uani 1 1 d . . . . . H17 H 1.020667 0.814265 0.781376 0.019 Uiso 1 1 calc R U . . . C18 C 0.8394(2) 0.71873(14) 0.84868(12) 0.0156(5) Uani 1 1 d . . . . . C19 C 0.9151(3) 0.73942(16) 0.90121(13) 0.0207(6) Uani 1 1 d . . . . . H19 H 0.916806 0.788935 0.913527 0.025 Uiso 1 1 calc R U . . . C20 C 0.9883(3) 0.68786(18) 0.93571(14) 0.0281(7) Uani 1 1 d . . . . . H20 H 1.040132 0.702438 0.971339 0.034 Uiso 1 1 calc R U . . . C21 C 0.9860(3) 0.61512(18) 0.91838(15) 0.0291(7) Uani 1 1 d . . . . . H21 H 1.034947 0.579973 0.942424 0.035 Uiso 1 1 calc R U . . . C22 C 0.9122(3) 0.59422(16) 0.86611(15) 0.0254(7) Uani 1 1 d . . . . . H22 H 0.910920 0.544601 0.854078 0.030 Uiso 1 1 calc R U . . . C23 C 0.8397(3) 0.64559(14) 0.83087(14) 0.0191(6) Uani 1 1 d . . . . . H23 H 0.790206 0.630934 0.794616 0.023 Uiso 1 1 calc R U . . . C24 C 0.4850(2) 0.55825(13) 0.76284(11) 0.0117(5) Uani 1 1 d . . . . . C25 C 0.4475(2) 0.59019(13) 0.85544(11) 0.0112(5) Uani 1 1 d . . . . . C26 C 0.3787(2) 0.52753(13) 0.83830(11) 0.0119(5) Uani 1 1 d . . . . . C27 C 0.5319(2) 0.56093(13) 0.70310(11) 0.0126(5) Uani 1 1 d . . . . . C28 C 0.5094(3) 0.50115(14) 0.66470(12) 0.0152(5) Uani 1 1 d . . . . . H28 H 0.468360 0.458576 0.678026 0.018 Uiso 1 1 calc R U . . . C29 C 0.5477(3) 0.50460(14) 0.60687(12) 0.0176(5) Uani 1 1 d . . . . . C30 C 0.6100(3) 0.56585(14) 0.58705(12) 0.0174(5) Uani 1 1 d . . . . . H30 H 0.635348 0.567704 0.547356 0.021 Uiso 1 1 calc R U . . . C31 C 0.6350(3) 0.62441(14) 0.62582(12) 0.0149(5) Uani 1 1 d . . . . . C32 C 0.5957(2) 0.62311(13) 0.68376(11) 0.0136(5) Uani 1 1 d . . . . . H32 H 0.611743 0.663709 0.709786 0.016 Uiso 1 1 calc R U . . . C33 C 0.4762(4) 0.38233(17) 0.58675(16) 0.0380(9) Uani 1 1 d . . . . . H33A H 0.469872 0.346606 0.554028 0.057 Uiso 1 1 calc R U . . . H33B H 0.388848 0.390725 0.599754 0.057 Uiso 1 1 calc R U . . . H33C H 0.535041 0.363793 0.620641 0.057 Uiso 1 1 calc R U . . . C34 C 0.7363(4) 0.74090(17) 0.64192(14) 0.0315(7) Uani 1 1 d . . . . . H34A H 0.785374 0.776706 0.620603 0.047 Uiso 1 1 calc R U . . . H34B H 0.791613 0.723026 0.677208 0.047 Uiso 1 1 calc R U . . . H34C H 0.657372 0.763814 0.654822 0.047 Uiso 1 1 calc R U . . . C35 C 0.4565(3) 0.63505(13) 0.91018(11) 0.0131(5) Uani 1 1 d . . . . . C36 C 0.5761(3) 0.66514(14) 0.93330(12) 0.0152(5) Uani 1 1 d . . . . . H36 H 0.652303 0.656802 0.913325 0.018 Uiso 1 1 calc R U . . . C37 C 0.5850(3) 0.70722(14) 0.98524(12) 0.0187(5) Uani 1 1 d . . . . . H37 H 0.667129 0.727358 1.000588 0.022 Uiso 1 1 calc R U . . . C38 C 0.4745(3) 0.71981(15) 1.01463(12) 0.0197(6) Uani 1 1 d . . . . . H38 H 0.480746 0.748231 1.050316 0.024 Uiso 1 1 calc R U . . . C39 C 0.3547(3) 0.69081(15) 0.99181(13) 0.0204(6) Uani 1 1 d . . . . . H39 H 0.278677 0.699871 1.011736 0.024 Uiso 1 1 calc R U . . . C40 C 0.3451(3) 0.64852(14) 0.93994(12) 0.0169(5) Uani 1 1 d . . . . . H40 H 0.262691 0.628736 0.924664 0.020 Uiso 1 1 calc R U . . . C41 C 0.2829(2) 0.48534(13) 0.86946(11) 0.0119(5) Uani 1 1 d . . . . . C42 C 0.3011(3) 0.46870(14) 0.93077(12) 0.0146(5) Uani 1 1 d . . . . . H42 H 0.379151 0.483449 0.954273 0.018 Uiso 1 1 calc R U . . . C43 C 0.2046(3) 0.43044(14) 0.95732(12) 0.0158(5) Uani 1 1 d . . . . . H43 H 0.217324 0.419215 0.998989 0.019 Uiso 1 1 calc R U . . . C44 C 0.0902(3) 0.40857(14) 0.92368(12) 0.0163(5) Uani 1 1 d . . . . . H44 H 0.024272 0.383137 0.942257 0.020 Uiso 1 1 calc R U . . . C45 C 0.0726(3) 0.42412(14) 0.86253(12) 0.0155(5) Uani 1 1 d . . . . . H45 H -0.004930 0.408525 0.839049 0.019 Uiso 1 1 calc R U . . . C46 C 0.1679(2) 0.46236(13) 0.83577(12) 0.0139(5) Uani 1 1 d . . . . . H46 H 0.154926 0.473074 0.794019 0.017 Uiso 1 1 calc R U . . . C47 C 0.7452(4) 0.4125(2) 0.47984(16) 0.0400(8) Uani 1 1 d . . . . . H47 H 0.651381 0.421859 0.486201 0.048 Uiso 1 1 calc R U . . . H1 H 0.641(3) 0.9021(19) 0.7513(14) 0.015(8) Uiso 1 1 d . . . . . H3 H 0.548(3) 0.6433(19) 0.8034(15) 0.019(9) Uiso 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 Cl1 0.0518(6) 0.0597(6) 0.0378(5) -0.0094(4) 0.0079(4) -0.0021(5) Cl2 0.0687(7) 0.0470(6) 0.0513(6) -0.0031(5) 0.0207(5) -0.0049(5) Cl3 0.0670(7) 0.0599(7) 0.0407(6) 0.0059(5) -0.0061(5) 0.0135(5) O1 0.0126(9) 0.0136(9) 0.0275(10) 0.0057(8) -0.0003(7) -0.0033(7) O2 0.0152(9) 0.0186(9) 0.0198(10) 0.0078(7) -0.0029(7) -0.0018(7) O3 0.0437(13) 0.0175(10) 0.0194(10) -0.0078(8) 0.0127(9) -0.0123(9) O4 0.0281(10) 0.0141(9) 0.0189(10) 0.0022(7) 0.0078(8) -0.0068(8) N1 0.0121(10) 0.0071(10) 0.0152(11) 0.0012(8) 0.0011(8) 0.0006(8) N2 0.0110(10) 0.0084(9) 0.0157(10) 0.0000(8) 0.0009(8) -0.0003(8) N3 0.0125(10) 0.0070(10) 0.0153(11) 0.0000(8) 0.0029(8) -0.0014(8) N4 0.0122(10) 0.0092(9) 0.0149(10) -0.0002(8) 0.0026(8) 0.0005(8) C1 0.0119(11) 0.0091(11) 0.0137(12) -0.0008(9) 0.0023(9) 0.0009(9) C2 0.0112(11) 0.0124(11) 0.0130(12) -0.0006(9) 0.0011(9) 0.0008(9) C3 0.0103(11) 0.0116(11) 0.0152(12) 0.0007(9) 0.0006(9) 0.0003(9) C4 0.0106(11) 0.0095(11) 0.0145(12) -0.0015(9) 0.0013(9) 0.0030(9) C5 0.0121(12) 0.0106(11) 0.0159(12) 0.0011(9) 0.0001(9) 0.0020(9) C6 0.0116(12) 0.0104(11) 0.0207(13) -0.0018(10) 0.0041(10) -0.0001(9) C7 0.0111(11) 0.0129(12) 0.0176(12) -0.0009(9) -0.0009(9) 0.0013(9) C8 0.0154(12) 0.0102(11) 0.0146(12) 0.0001(9) 0.0009(10) 0.0027(9) C9 0.0130(12) 0.0105(11) 0.0179(13) 0.0008(9) 0.0014(10) 0.0000(9) C10 0.0201(14) 0.0172(13) 0.0298(16) 0.0096(11) 0.0021(12) -0.0028(11) C11 0.0200(14) 0.0196(13) 0.0270(15) 0.0108(11) -0.0017(11) -0.0035(11) C12 0.0135(12) 0.0129(11) 0.0128(12) 0.0021(9) -0.0010(9) -0.0014(9) C13 0.0167(12) 0.0137(12) 0.0179(13) -0.0018(10) -0.0003(10) -0.0011(10) C14 0.0232(14) 0.0146(12) 0.0234(14) -0.0034(11) -0.0010(11) -0.0038(11) C15 0.0208(14) 0.0210(14) 0.0232(14) 0.0003(11) -0.0026(11) -0.0098(11) C16 0.0143(13) 0.0228(14) 0.0223(14) 0.0010(11) 0.0019(10) -0.0025(11) C17 0.0148(12) 0.0133(12) 0.0195(13) 0.0002(10) -0.0002(10) -0.0007(10) C18 0.0108(12) 0.0152(12) 0.0212(13) 0.0064(10) 0.0038(10) 0.0010(10) C19 0.0159(13) 0.0229(14) 0.0227(14) 0.0072(11) -0.0013(11) -0.0025(11) C20 0.0168(14) 0.0401(18) 0.0268(16) 0.0172(13) -0.0011(12) -0.0025(13) C21 0.0144(13) 0.0333(17) 0.0408(18) 0.0263(14) 0.0084(12) 0.0072(12) C22 0.0158(13) 0.0200(14) 0.0422(18) 0.0138(13) 0.0124(12) 0.0053(11) C23 0.0134(12) 0.0157(13) 0.0292(15) 0.0059(11) 0.0061(11) 0.0040(10) C24 0.0111(11) 0.0074(11) 0.0163(12) 0.0014(9) -0.0002(9) 0.0010(9) C25 0.0110(11) 0.0090(11) 0.0136(12) 0.0004(9) 0.0017(9) 0.0013(9) C26 0.0122(11) 0.0107(11) 0.0127(12) 0.0005(9) 0.0014(9) 0.0007(9) C27 0.0120(11) 0.0105(11) 0.0152(12) 0.0007(9) 0.0009(9) 0.0013(9) C28 0.0157(12) 0.0122(12) 0.0181(13) -0.0019(10) 0.0043(10) -0.0021(10) C29 0.0195(13) 0.0158(12) 0.0173(13) -0.0032(10) 0.0016(10) -0.0011(10) C30 0.0201(13) 0.0182(13) 0.0143(12) 0.0017(10) 0.0039(10) -0.0005(10) C31 0.0146(12) 0.0125(12) 0.0177(13) 0.0043(10) 0.0022(10) 0.0002(9) C32 0.0146(12) 0.0112(11) 0.0150(12) 0.0007(9) 0.0015(9) -0.0001(9) C33 0.067(2) 0.0190(15) 0.0317(18) -0.0120(13) 0.0232(17) -0.0210(16) C34 0.049(2) 0.0227(15) 0.0241(16) -0.0012(12) 0.0085(14) -0.0200(14) C35 0.0174(12) 0.0074(11) 0.0146(12) 0.0019(9) 0.0014(10) 0.0003(9) C36 0.0154(12) 0.0139(12) 0.0165(13) 0.0008(10) 0.0022(10) -0.0007(10) C37 0.0199(13) 0.0145(12) 0.0205(13) 0.0002(10) -0.0032(10) -0.0019(10) C38 0.0293(15) 0.0138(12) 0.0156(13) -0.0031(10) 0.0011(11) 0.0006(11) C39 0.0233(14) 0.0180(13) 0.0210(14) -0.0032(11) 0.0077(11) 0.0016(11) C40 0.0172(13) 0.0149(12) 0.0190(13) -0.0028(10) 0.0030(10) -0.0019(10) C41 0.0134(12) 0.0072(10) 0.0157(12) -0.0008(9) 0.0039(9) -0.0002(9) C42 0.0147(12) 0.0134(12) 0.0157(12) -0.0003(9) 0.0011(10) -0.0010(9) C43 0.0205(13) 0.0135(12) 0.0137(12) 0.0005(9) 0.0030(10) 0.0005(10) C44 0.0170(12) 0.0127(12) 0.0201(13) 0.0016(10) 0.0068(10) -0.0012(10) C45 0.0138(12) 0.0128(12) 0.0196(13) -0.0012(10) 0.0008(10) -0.0022(10) C46 0.0166(12) 0.0103(11) 0.0150(12) -0.0001(9) 0.0028(10) 0.0008(9) C47 0.042(2) 0.045(2) 0.0339(19) -0.0015(16) 0.0068(15) 0.0073(17) _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 Cl1 C47 1.750(4) . ? Cl2 C47 1.759(4) . ? Cl3 C47 1.758(4) . ? O1 C6 1.367(3) . ? O1 C10 1.433(3) . ? O2 C8 1.363(3) . ? O2 C11 1.433(3) . ? O3 C29 1.365(3) . ? O3 C33 1.434(4) . ? O4 C31 1.366(3) . ? O4 C34 1.426(3) . ? N1 C1 1.355(3) . ? N1 C2 1.383(3) . ? N1 H1 0.79(3) . ? N2 C1 1.328(3) . ? N2 C3 1.387(3) . ? N3 C24 1.359(3) . ? N3 C25 1.379(3) . ? N3 H3 0.74(4) . ? N4 C24 1.335(3) . ? N4 C26 1.380(3) . ? C1 C4 1.471(3) . ? C2 C3 1.378(3) . ? C2 C12 1.469(3) . ? C3 C18 1.471(3) . ? C4 C5 1.398(3) . ? C4 C9 1.403(3) . ? C5 C6 1.398(4) . ? C5 H5 0.9500 . ? C6 C7 1.381(4) . ? C7 C8 1.390(4) . ? C7 H7 0.9500 . ? C8 C9 1.397(4) . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C17 1.398(4) . ? C12 C13 1.401(4) . ? C13 C14 1.388(4) . ? C13 H13 0.9500 . ? C14 C15 1.384(4) . ? C14 H14 0.9500 . ? C15 C16 1.392(4) . ? C15 H15 0.9500 . ? C16 C17 1.382(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.393(4) . ? C18 C23 1.401(4) . ? C19 C20 1.391(4) . ? C19 H19 0.9500 . ? C20 C21 1.391(5) . ? C20 H20 0.9500 . ? C21 C22 1.380(5) . ? C21 H21 0.9500 . ? C22 C23 1.394(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C27 1.465(3) . ? C25 C26 1.383(3) . ? C25 C35 1.471(3) . ? C26 C41 1.478(3) . ? C27 C28 1.398(3) . ? C27 C32 1.405(3) . ? C28 C29 1.390(4) . ? C28 H28 0.9500 . ? C29 C30 1.388(4) . ? C30 C31 1.389(4) . ? C30 H30 0.9500 . ? C31 C32 1.395(4) . ? C32 H32 0.9500 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.394(4) . ? C35 C40 1.399(4) . ? C36 C37 1.390(4) . ? C36 H36 0.9500 . ? C37 C38 1.384(4) . ? C37 H37 0.9500 . ? C38 C39 1.386(4) . ? C38 H38 0.9500 . ? C39 C40 1.391(4) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 C46 1.397(4) . ? C41 C42 1.398(4) . ? C42 C43 1.394(4) . ? C42 H42 0.9500 . ? C43 C44 1.386(4) . ? C43 H43 0.9500 . ? C44 C45 1.390(4) . ? C44 H44 0.9500 . ? C45 C46 1.387(4) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 H47 1.0000 . ? 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 C6 O1 C10 117.2(2) . . ? C8 O2 C11 117.0(2) . . ? C29 O3 C33 117.3(2) . . ? C31 O4 C34 117.7(2) . . ? C1 N1 C2 108.2(2) . . ? C1 N1 H1 125(2) . . ? C2 N1 H1 127(2) . . ? C1 N2 C3 106.0(2) . . ? C24 N3 C25 108.5(2) . . ? C24 N3 H3 125(3) . . ? C25 N3 H3 125(3) . . ? C24 N4 C26 106.3(2) . . ? N2 C1 N1 110.9(2) . . ? N2 C1 C4 123.9(2) . . ? N1 C1 C4 125.1(2) . . ? C3 C2 N1 105.2(2) . . ? C3 C2 C12 132.1(2) . . ? N1 C2 C12 122.6(2) . . ? C2 C3 N2 109.7(2) . . ? C2 C3 C18 130.5(2) . . ? N2 C3 C18 119.8(2) . . ? C5 C4 C9 120.9(2) . . ? C5 C4 C1 118.8(2) . . ? C9 C4 C1 120.2(2) . . ? C4 C5 C6 118.8(2) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? O1 C6 C7 114.7(2) . . ? O1 C6 C5 124.3(2) . . ? C7 C6 C5 121.0(2) . . ? C6 C7 C8 119.7(2) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? O2 C8 C7 115.1(2) . . ? O2 C8 C9 124.0(2) . . ? C7 C8 C9 120.9(2) . . ? C8 C9 C4 118.7(2) . . ? C8 C9 H9 120.7 . . ? C4 C9 H9 120.7 . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 118.6(2) . . ? C17 C12 C2 120.2(2) . . ? C13 C12 C2 121.1(2) . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 120.4(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.7(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 120.2(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C12 120.7(2) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? C19 C18 C23 119.0(2) . . ? C19 C18 C3 121.6(2) . . ? C23 C18 C3 119.3(2) . . ? C20 C19 C18 120.3(3) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 120.4(3) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C22 C21 C20 119.7(3) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 120.3(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C18 120.3(3) . . ? C22 C23 H23 119.9 . . ? C18 C23 H23 119.9 . . ? N4 C24 N3 110.3(2) . . ? N4 C24 C27 124.9(2) . . ? N3 C24 C27 124.8(2) . . ? N3 C25 C26 105.2(2) . . ? N3 C25 C35 121.7(2) . . ? C26 C25 C35 133.1(2) . . ? N4 C26 C25 109.7(2) . . ? N4 C26 C41 119.6(2) . . ? C25 C26 C41 130.5(2) . . ? C28 C27 C32 120.1(2) . . ? C28 C27 C24 119.0(2) . . ? C32 C27 C24 120.9(2) . . ? C29 C28 C27 119.4(2) . . ? C29 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? O3 C29 C30 115.6(2) . . ? O3 C29 C28 123.3(2) . . ? C30 C29 C28 121.0(2) . . ? C29 C30 C31 119.4(2) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? O4 C31 C30 115.1(2) . . ? O4 C31 C32 124.0(2) . . ? C30 C31 C32 120.9(2) . . ? C31 C32 C27 119.1(2) . . ? C31 C32 H32 120.5 . . ? C27 C32 H32 120.5 . . ? O3 C33 H33A 109.5 . . ? O3 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O3 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O4 C34 H34A 109.5 . . ? O4 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O4 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C36 C35 C40 118.7(2) . . ? C36 C35 C25 120.6(2) . . ? C40 C35 C25 120.6(2) . . ? C37 C36 C35 120.8(2) . . ? C37 C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C38 C37 C36 120.1(3) . . ? C38 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? C37 C38 C39 119.8(2) . . ? C37 C38 H38 120.1 . . ? C39 C38 H38 120.1 . . ? C38 C39 C40 120.5(3) . . ? C38 C39 H39 119.8 . . ? C40 C39 H39 119.8 . . ? C39 C40 C35 120.2(3) . . ? C39 C40 H40 119.9 . . ? C35 C40 H40 119.9 . . ? C46 C41 C42 118.9(2) . . ? C46 C41 C26 117.8(2) . . ? C42 C41 C26 123.2(2) . . ? C43 C42 C41 119.9(2) . . ? C43 C42 H42 120.1 . . ? C41 C42 H42 120.1 . . ? C44 C43 C42 120.8(2) . . ? C44 C43 H43 119.6 . . ? C42 C43 H43 119.6 . . ? C43 C44 C45 119.5(2) . . ? C43 C44 H44 120.2 . . ? C45 C44 H44 120.2 . . ? C46 C45 C44 120.1(2) . . ? C46 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? C45 C46 C41 120.8(2) . . ? C45 C46 H46 119.6 . . ? C41 C46 H46 119.6 . . ? Cl1 C47 Cl3 111.0(2) . . ? Cl1 C47 Cl2 110.3(2) . . ? Cl3 C47 Cl2 109.8(2) . . ? Cl1 C47 H47 108.6 . . ? Cl3 C47 H47 108.6 . . ? Cl2 C47 H47 108.6 . . ? _refine_diff_density_max 1.274 _refine_diff_density_min -1.052 _refine_diff_density_rms 0.092 _shelx_res_file ; TITL i18108_a.res in P2(1)/c i18108.res created by SHELXL-2018/3 at 16:51:40 on 03-Feb-2021 REM Old TITL i18108 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.149, Rweak 0.009, Alpha 0.024, Orientation as input REM Formula found by SHELXT: C47 Cl3 N5 O3 CELL 0.71073 10.2370 18.3683 22.3540 90.000 95.807 90.000 ZERR 4.000 0.0004 0.0006 0.0008 0.000 0.001 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H CL N O UNIT 188 164 12 16 16 ACTA TEMP -173.150 SIZE 0.04 0.155 0.216 L.S. 10 BOND $H LIST 6 OMIT -2 0 2 OMIT -2 1 1 FMAP 2 PLAN 5 WGHT 0.096900 7.471700 FVAR 0.38034 CL1 3 0.749557 0.360092 0.414720 11.00000 0.05177 0.05975 = 0.03783 -0.00937 0.00785 -0.00208 CL2 3 0.823480 0.496642 0.471607 11.00000 0.06871 0.04702 = 0.05133 -0.00310 0.02073 -0.00493 CL3 3 0.820714 0.366527 0.543106 11.00000 0.06702 0.05989 = 0.04075 0.00588 -0.00607 0.01352 O1 5 0.129318 0.703318 0.723987 11.00000 0.01257 0.01358 = 0.02754 0.00573 -0.00032 -0.00326 O2 5 0.241072 0.896118 0.605559 11.00000 0.01520 0.01859 = 0.01975 0.00783 -0.00286 -0.00181 O3 5 0.527169 0.449471 0.566020 11.00000 0.04374 0.01748 = 0.01941 -0.00775 0.01275 -0.01232 O4 5 0.699251 0.681455 0.602794 11.00000 0.02815 0.01412 = 0.01893 0.00217 0.00784 -0.00682 N1 4 0.656767 0.863908 0.766432 11.00000 0.01213 0.00709 = 0.01524 0.00118 0.00107 0.00058 N2 4 0.625974 0.749697 0.792699 11.00000 0.01104 0.00835 = 0.01569 -0.00002 0.00087 -0.00031 N3 4 0.515071 0.607961 0.807118 11.00000 0.01247 0.00703 = 0.01534 -0.00003 0.00289 -0.00138 N4 4 0.403249 0.508059 0.780897 11.00000 0.01217 0.00920 = 0.01489 -0.00017 0.00262 0.00053 C1 1 0.571445 0.807328 0.764319 11.00000 0.01185 0.00910 = 0.01370 -0.00081 0.00229 0.00091 C2 1 0.773227 0.841776 0.797968 11.00000 0.01119 0.01237 = 0.01299 -0.00064 0.00108 0.00079 C3 1 0.752400 0.770546 0.813918 11.00000 0.01035 0.01161 = 0.01520 0.00067 0.00061 0.00027 C4 1 0.438925 0.807405 0.732023 11.00000 0.01063 0.00948 = 0.01452 -0.00155 0.00126 0.00299 C5 1 0.348056 0.755647 0.747508 11.00000 0.01209 0.01059 = 0.01593 0.00108 0.00008 0.00199 AFIX 43 H5 2 0.368804 0.723856 0.780630 11.00000 -1.20000 AFIX 0 C6 1 0.226087 0.751523 0.713361 11.00000 0.01161 0.01039 = 0.02075 -0.00182 0.00407 -0.00007 C7 1 0.194458 0.798136 0.665603 11.00000 0.01108 0.01288 = 0.01760 -0.00094 -0.00087 0.00132 AFIX 43 H7 2 0.112227 0.793832 0.642046 11.00000 -1.20000 AFIX 0 C8 1 0.283465 0.851374 0.652157 11.00000 0.01543 0.01025 = 0.01464 0.00008 0.00085 0.00266 C9 1 0.407159 0.856278 0.684561 11.00000 0.01299 0.01046 = 0.01794 0.00075 0.00137 0.00001 AFIX 43 H9 2 0.468545 0.891996 0.674657 11.00000 -1.20000 AFIX 0 C10 1 0.158711 0.651586 0.771396 11.00000 0.02013 0.01724 = 0.02979 0.00962 0.00207 -0.00277 AFIX 137 H10A 2 0.083579 0.618937 0.773441 11.00000 -1.50000 H10B 2 0.176657 0.677355 0.809734 11.00000 -1.50000 H10C 2 0.236006 0.623074 0.763446 11.00000 -1.50000 AFIX 0 C11 1 0.326896 0.954265 0.592265 11.00000 0.01996 0.01961 = 0.02704 0.01082 -0.00169 -0.00346 AFIX 137 H11A 2 0.409223 0.933990 0.580666 11.00000 -1.50000 H11B 2 0.345444 0.985025 0.627933 11.00000 -1.50000 H11C 2 0.284712 0.983541 0.559103 11.00000 -1.50000 AFIX 0 C12 1 0.889317 0.889070 0.806746 11.00000 0.01346 0.01290 = 0.01280 0.00206 -0.00102 -0.00144 C13 1 0.878918 0.961577 0.825058 11.00000 0.01665 0.01368 = 0.01785 -0.00183 -0.00028 -0.00108 AFIX 43 H13 2 0.796491 0.980015 0.834133 11.00000 -1.20000 AFIX 0 C14 1 0.988318 1.006681 0.830034 11.00000 0.02316 0.01458 = 0.02344 -0.00340 -0.00100 -0.00384 AFIX 43 H14 2 0.980374 1.055732 0.842644 11.00000 -1.20000 AFIX 0 C15 1 1.108861 0.980596 0.816730 11.00000 0.02082 0.02102 = 0.02316 0.00033 -0.00264 -0.00983 AFIX 43 H15 2 1.183331 1.011737 0.819798 11.00000 -1.20000 AFIX 0 C16 1 1.120444 0.908506 0.798831 11.00000 0.01432 0.02280 = 0.02227 0.00100 0.00186 -0.00252 AFIX 43 H16 2 1.203235 0.890284 0.790052 11.00000 -1.20000 AFIX 0 C17 1 1.011900 0.863337 0.793786 11.00000 0.01478 0.01333 = 0.01949 0.00024 -0.00022 -0.00074 AFIX 43 H17 2 1.020667 0.814265 0.781376 11.00000 -1.20000 AFIX 0 C18 1 0.839401 0.718727 0.848680 11.00000 0.01082 0.01524 = 0.02119 0.00637 0.00381 0.00099 C19 1 0.915109 0.739417 0.901206 11.00000 0.01589 0.02292 = 0.02269 0.00723 -0.00126 -0.00252 AFIX 43 H19 2 0.916806 0.788935 0.913527 11.00000 -1.20000 AFIX 0 C20 1 0.988266 0.687856 0.935707 11.00000 0.01680 0.04011 = 0.02678 0.01721 -0.00106 -0.00252 AFIX 43 H20 2 1.040132 0.702438 0.971339 11.00000 -1.20000 AFIX 0 C21 1 0.985971 0.615118 0.918379 11.00000 0.01444 0.03330 = 0.04084 0.02626 0.00842 0.00722 AFIX 43 H21 2 1.034947 0.579973 0.942424 11.00000 -1.20000 AFIX 0 C22 1 0.912248 0.594220 0.866111 11.00000 0.01583 0.01997 = 0.04220 0.01383 0.01243 0.00527 AFIX 43 H22 2 0.910920 0.544601 0.854078 11.00000 -1.20000 AFIX 0 C23 1 0.839678 0.645588 0.830865 11.00000 0.01341 0.01565 = 0.02918 0.00595 0.00605 0.00398 AFIX 43 H23 2 0.790206 0.630934 0.794616 11.00000 -1.20000 AFIX 0 C24 1 0.484982 0.558252 0.762836 11.00000 0.01114 0.00741 = 0.01635 0.00139 -0.00018 0.00101 C25 1 0.447522 0.590188 0.855436 11.00000 0.01100 0.00898 = 0.01358 0.00041 0.00174 0.00133 C26 1 0.378673 0.527532 0.838299 11.00000 0.01225 0.01073 = 0.01274 0.00051 0.00137 0.00072 C27 1 0.531939 0.560927 0.703098 11.00000 0.01201 0.01046 = 0.01519 0.00074 0.00086 0.00127 C28 1 0.509428 0.501154 0.664699 11.00000 0.01573 0.01219 = 0.01808 -0.00185 0.00428 -0.00212 AFIX 43 H28 2 0.468360 0.458576 0.678026 11.00000 -1.20000 AFIX 0 C29 1 0.547679 0.504602 0.606867 11.00000 0.01950 0.01575 = 0.01734 -0.00318 0.00159 -0.00110 C30 1 0.610004 0.565855 0.587053 11.00000 0.02013 0.01822 = 0.01425 0.00172 0.00388 -0.00050 AFIX 43 H30 2 0.635348 0.567704 0.547356 11.00000 -1.20000 AFIX 0 C31 1 0.634954 0.624414 0.625824 11.00000 0.01458 0.01247 = 0.01771 0.00429 0.00222 0.00021 C32 1 0.595653 0.623108 0.683756 11.00000 0.01459 0.01120 = 0.01503 0.00067 0.00153 -0.00013 AFIX 43 H32 2 0.611743 0.663709 0.709786 11.00000 -1.20000 AFIX 0 C33 1 0.476197 0.382334 0.586752 11.00000 0.06712 0.01899 = 0.03170 -0.01197 0.02318 -0.02100 AFIX 137 H33A 2 0.469872 0.346606 0.554028 11.00000 -1.50000 H33B 2 0.388848 0.390725 0.599754 11.00000 -1.50000 H33C 2 0.535041 0.363793 0.620641 11.00000 -1.50000 AFIX 0 C34 1 0.736300 0.740899 0.641916 11.00000 0.04859 0.02268 = 0.02413 -0.00122 0.00853 -0.01999 AFIX 137 H34A 2 0.785374 0.776706 0.620603 11.00000 -1.50000 H34B 2 0.791613 0.723026 0.677208 11.00000 -1.50000 H34C 2 0.657372 0.763814 0.654822 11.00000 -1.50000 AFIX 0 C35 1 0.456501 0.635048 0.910185 11.00000 0.01745 0.00737 = 0.01456 0.00187 0.00143 0.00026 C36 1 0.576060 0.665141 0.933298 11.00000 0.01535 0.01385 = 0.01649 0.00075 0.00217 -0.00068 AFIX 43 H36 2 0.652303 0.656802 0.913325 11.00000 -1.20000 AFIX 0 C37 1 0.585029 0.707220 0.985244 11.00000 0.01988 0.01450 = 0.02055 0.00018 -0.00317 -0.00186 AFIX 43 H37 2 0.667129 0.727358 1.000588 11.00000 -1.20000 AFIX 0 C38 1 0.474527 0.719813 1.014633 11.00000 0.02928 0.01381 = 0.01564 -0.00307 0.00107 0.00059 AFIX 43 H38 2 0.480746 0.748231 1.050316 11.00000 -1.20000 AFIX 0 C39 1 0.354734 0.690808 0.991810 11.00000 0.02331 0.01798 = 0.02095 -0.00316 0.00775 0.00157 AFIX 43 H39 2 0.278677 0.699871 1.011736 11.00000 -1.20000 AFIX 0 C40 1 0.345126 0.648523 0.939936 11.00000 0.01716 0.01495 = 0.01895 -0.00275 0.00297 -0.00194 AFIX 43 H40 2 0.262691 0.628736 0.924664 11.00000 -1.20000 AFIX 0 C41 1 0.282929 0.485339 0.869461 11.00000 0.01343 0.00718 = 0.01567 -0.00080 0.00391 -0.00021 C42 1 0.301128 0.468702 0.930766 11.00000 0.01469 0.01336 = 0.01572 -0.00029 0.00115 -0.00104 AFIX 43 H42 2 0.379151 0.483449 0.954273 11.00000 -1.20000 AFIX 0 C43 1 0.204568 0.430439 0.957322 11.00000 0.02048 0.01355 = 0.01367 0.00045 0.00301 0.00053 AFIX 43 H43 2 0.217324 0.419215 0.998989 11.00000 -1.20000 AFIX 0 C44 1 0.090169 0.408568 0.923675 11.00000 0.01698 0.01269 = 0.02010 0.00158 0.00680 -0.00122 AFIX 43 H44 2 0.024272 0.383137 0.942257 11.00000 -1.20000 AFIX 0 C45 1 0.072552 0.424118 0.862532 11.00000 0.01379 0.01279 = 0.01964 -0.00119 0.00077 -0.00218 AFIX 43 H45 2 -0.004930 0.408525 0.839049 11.00000 -1.20000 AFIX 0 C46 1 0.167940 0.462364 0.835774 11.00000 0.01656 0.01029 = 0.01504 -0.00011 0.00279 0.00076 AFIX 43 H46 2 0.154926 0.473074 0.794019 11.00000 -1.20000 AFIX 0 C47 1 0.745212 0.412518 0.479836 11.00000 0.04201 0.04482 = 0.03390 -0.00155 0.00678 0.00725 AFIX 13 H47 2 0.651381 0.421859 0.486201 11.00000 -1.20000 REM ##### AFIX 0 H1 2 0.641485 0.902087 0.751344 11.00000 0.01489 H3 2 0.548200 0.643255 0.803350 11.00000 0.01897 HKLF 4 REM i18108_a.res in P2(1)/c REM wR2 = 0.192783, GooF = S = 1.05387, Restrained GooF = 1.05387 for all data REM R1 = 0.062669 for 7022 Fo > 4sig(Fo) and 0.085677 for all 9215 data REM 535 parameters refined using 0 restraints END WGHT 0.0969 7.4724 REM Highest difference peak 1.274, deepest hole -1.052, 1-sigma level 0.092 Q1 1 0.9229 0.3117 0.4679 11.00000 0.05 1.27 Q2 1 0.8444 0.3589 0.4723 11.00000 0.05 1.16 Q3 1 0.8625 0.4171 0.5277 11.00000 0.05 0.73 Q4 1 1.0137 0.3400 0.4504 11.00000 0.05 0.66 Q5 1 0.7427 0.4006 0.4399 11.00000 0.05 0.41 ; _shelx_res_checksum 14709