# Electronic Supplementary Material (ESI) for ChemComm. # 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_LXF_182_0ma _database_code_depnum_ccdc_archive 'CCDC 2077271' loop_ _audit_author_name _audit_author_address 'Giasemi Angeli' ;University of Crete Greece ; _audit_update_record ; 2021-04-13 deposited with the CCDC. 2021-06-09 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 ? _chemical_formula_sum 'C20 H21 N5 O4' _chemical_formula_weight 395.42 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 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 9.5268(3) _cell_length_b 25.0880(8) _cell_length_c 8.4177(3) _cell_angle_alpha 90 _cell_angle_beta 111.280(2) _cell_angle_gamma 90 _cell_volume 1874.72(11) _cell_formula_units_Z 4 _cell_measurement_temperature 215(2) _cell_measurement_reflns_used 5363 _cell_measurement_theta_min 3.52 _cell_measurement_theta_max 50.38 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_F_000 832 _exptl_transmission_factor_min 0.6061 _exptl_transmission_factor_max 0.7500 _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_absorpt_coefficient_mu 0.831 _shelx_estimated_absorpt_T_min 0.6061 _shelx_estimated_absorpt_T_max 0.7500 _exptl_absorpt_correction_type ?multi-scan? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS-2016/2--Bruker _exptl_absorpt_special_details ? _diffrn_ambient_temperature 215(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 10266 _diffrn_reflns_av_unetI/netI 0.0384 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.523 _diffrn_reflns_theta_max 50.505 _diffrn_reflns_theta_full 50.505 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_point_group_measured_fraction_full 0.996 _reflns_number_total 1965 _reflns_number_gt 1606 _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 ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^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_number_reflns 1965 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1934 _refine_ls_wR_factor_gt 0.1793 _refine_ls_goodness_of_fit_ref 1.435 _refine_ls_restrained_S_all 1.435 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # start Validation Reply Form _vrf_THETM01_LXF_182_0ma ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550 RESPONSE: These were weakly diffracting crystals, especially in higher angles. Although a high-brilliance IuS microfocus with Cu radiation was used reasonable diffraction data could be obtained only to moderate resolution, despite multiple attempts to improve crystal quality. ; # end Validation Reply Form 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 0.1002(3) 0.36654(11) 0.8661(3) 0.0545(9) Uani 1 1 d . . . . . O2 O 0.3977(3) 0.33491(13) 0.9955(4) 0.0634(10) Uani 1 1 d . . . . . H7 H 0.350990 0.332352 1.081518 0.076 Uiso 1 1 calc R U . . . H6 H 0.507106 0.333268 1.055381 0.076 Uiso 1 1 calc R U . . . O3 O 0.0224(3) 0.46189(12) 0.7183(4) 0.0578(9) Uani 1 1 d . . . . . O4 O 0.7321(4) 0.42291(13) 0.9283(4) 0.0621(10) Uani 1 1 d . . . . . N2 N 0.5152(5) 0.49856(14) 0.7608(4) 0.0462(11) Uani 1 1 d . . . . . H8 H 0.610(5) 0.4971(16) 0.785(5) 0.045(14) Uiso 1 1 d . . . . . N3 N 0.4121(4) 0.61841(14) 0.4866(4) 0.0430(10) Uani 1 1 d . . . . . C1 C 0.3518(6) 0.28959(19) 0.8843(7) 0.0804(17) Uani 1 1 d . . . . . H5 H 0.243815 0.290888 0.822987 0.121 Uiso 1 1 calc R U . . . H4 H 0.377606 0.257116 0.951230 0.121 Uiso 1 1 calc R U . . . H1 H 0.403088 0.290152 0.803603 0.121 Uiso 1 1 calc R U . . . C2 C 0.3620(5) 0.38359(17) 0.9165(5) 0.0448(12) Uani 1 1 d . . . . . C3 C 0.4763(5) 0.41443(17) 0.8988(5) 0.0450(12) Uani 1 1 d . . . . . C4 C 0.4308(5) 0.46294(17) 0.8113(5) 0.0424(11) Uani 1 1 d . . . . . C5 C 0.4218(5) 0.53876(17) 0.6668(5) 0.0447(12) Uani 1 1 d . . . . . C6 C 0.4867(5) 0.57962(16) 0.5937(5) 0.0436(12) Uani 1 1 d . . . . . C7 C 0.2539(5) 0.63222(17) 0.4172(5) 0.0459(12) Uani 1 1 d . . . . . H12 H 0.194033 0.599481 0.385483 0.055 Uiso 1 1 calc R U . . . H11 H 0.233843 0.653421 0.313482 0.055 Uiso 1 1 calc R U . . . C8 C 0.2047(5) 0.66356(16) 0.5423(5) 0.0406(11) Uani 1 1 d . . . . . C9 C 0.0583(5) 0.65967(17) 0.5357(5) 0.0485(12) Uani 1 1 d . . . . . H16 H -0.007850 0.635407 0.459876 0.058 Uiso 1 1 calc R U . . . N16 N 0.6325(4) 0.58410(15) 0.6217(4) 0.0532(11) Uani 1 1 d . . . . . C10 C 0.0070(5) 0.69113(19) 0.6398(5) 0.0545(13) Uani 1 1 d . . . . . H15 H -0.093577 0.688633 0.632593 0.065 Uiso 1 1 calc R U . . . N15 N 0.6448(4) 0.62750(16) 0.5291(5) 0.0594(11) Uani 1 1 d . . . . . C11 C 0.1046(6) 0.72585(18) 0.7530(5) 0.0567(13) Uani 1 1 d . . . . . H2 H 0.071089 0.747201 0.823931 0.068 Uiso 1 1 calc R U . . . C12 C 0.0846(6) 0.3609(2) 1.0272(5) 0.0716(15) Uani 1 1 d . . . . . H3 H 0.168572 0.340459 1.103032 0.107 Uiso 1 1 calc R U . . . H22 H -0.008964 0.342643 1.012419 0.107 Uiso 1 1 calc R U . . . H23 H 0.083667 0.395932 1.075829 0.107 Uiso 1 1 calc R U . . . C13 C 0.2114(5) 0.39972(19) 0.8576(5) 0.0468(12) Uani 1 1 d . . . . . N14 N 0.5146(5) 0.64801(15) 0.4484(4) 0.0535(10) Uani 1 1 d . . . . . C17 C 0.3017(5) 0.69788(17) 0.6580(5) 0.0481(12) Uani 1 1 d . . . . . H13 H 0.402733 0.700128 0.666874 0.058 Uiso 1 1 calc R U . . . C18 C 0.2505(5) 0.72925(17) 0.7620(5) 0.0541(13) Uani 1 1 d . . . . . H14 H 0.317064 0.753065 0.839430 0.065 Uiso 1 1 calc R U . . . C19 C 0.2785(5) 0.52940(17) 0.6592(5) 0.0476(12) Uani 1 1 d . . . . . H20 H 0.193528 0.550754 0.604545 0.057 Uiso 1 1 calc R U . . . C20 C 0.2818(5) 0.48114(17) 0.7498(5) 0.0433(11) Uani 1 1 d . . . . . C21 C 0.1709(5) 0.44920(18) 0.7765(5) 0.0462(11) Uani 1 1 d . . . . . C22 C -0.0205(6) 0.5136(2) 0.7431(7) 0.0814(17) Uani 1 1 d . . . . . H19 H 0.057975 0.529726 0.839627 0.122 Uiso 1 1 calc R U . . . H17 H -0.113494 0.512308 0.765276 0.122 Uiso 1 1 calc R U . . . H18 H -0.035663 0.534750 0.641684 0.122 Uiso 1 1 calc R U . . . C23 C 0.6328(6) 0.3976(2) 0.9539(5) 0.0572(13) Uani 1 1 d . . . . . H21 H 0.659256 0.365162 1.013134 0.069 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 0.049(2) 0.069(2) 0.0421(17) 0.0006(15) 0.0130(14) -0.0106(16) O2 0.048(2) 0.081(3) 0.0601(19) 0.017(2) 0.0178(16) 0.0055(17) O3 0.032(2) 0.059(2) 0.074(2) -0.0030(16) 0.0093(16) 0.0004(15) O4 0.040(2) 0.088(2) 0.058(2) 0.0039(17) 0.0171(16) 0.0038(18) N2 0.032(3) 0.060(3) 0.043(2) -0.0055(19) 0.010(2) 0.001(2) N3 0.035(2) 0.053(2) 0.040(2) -0.0008(18) 0.0137(18) -0.0044(19) C1 0.089(5) 0.052(3) 0.100(4) -0.003(3) 0.035(3) -0.003(3) C2 0.046(3) 0.050(3) 0.034(2) 0.008(2) 0.009(2) 0.007(2) C3 0.039(3) 0.058(3) 0.037(2) -0.002(2) 0.013(2) 0.005(2) C4 0.038(3) 0.053(3) 0.035(2) -0.006(2) 0.012(2) -0.001(2) C5 0.039(3) 0.050(3) 0.038(2) -0.006(2) 0.006(2) 0.003(2) C6 0.039(3) 0.050(3) 0.038(2) -0.006(2) 0.009(2) -0.001(2) C7 0.044(3) 0.051(3) 0.040(2) -0.001(2) 0.012(2) 0.003(2) C8 0.039(3) 0.049(3) 0.032(2) 0.004(2) 0.011(2) 0.000(2) C9 0.045(3) 0.059(3) 0.039(2) -0.003(2) 0.012(2) -0.005(2) N16 0.040(3) 0.067(3) 0.049(2) -0.004(2) 0.0108(18) -0.0046(19) C10 0.044(3) 0.071(3) 0.050(3) 0.001(3) 0.018(2) 0.002(3) N15 0.047(3) 0.072(3) 0.057(2) 0.002(2) 0.017(2) -0.008(2) C11 0.053(4) 0.065(3) 0.050(3) -0.011(2) 0.017(2) -0.005(3) C12 0.067(4) 0.102(4) 0.050(3) -0.005(3) 0.026(3) -0.013(3) C13 0.036(3) 0.064(3) 0.038(2) -0.004(2) 0.010(2) -0.005(3) N14 0.042(3) 0.069(3) 0.049(2) -0.0015(19) 0.016(2) -0.007(2) C17 0.044(3) 0.058(3) 0.041(2) 0.000(2) 0.013(2) 0.001(2) C18 0.050(4) 0.056(3) 0.049(3) -0.011(2) 0.010(2) -0.010(2) C19 0.036(3) 0.054(3) 0.047(3) 0.000(2) 0.007(2) 0.004(2) C20 0.033(3) 0.051(3) 0.044(2) -0.004(2) 0.013(2) 0.002(2) C21 0.032(3) 0.061(3) 0.042(2) -0.004(2) 0.009(2) 0.001(2) C22 0.052(4) 0.087(4) 0.101(4) -0.033(3) 0.023(3) 0.002(3) C23 0.053(4) 0.069(3) 0.046(3) -0.002(2) 0.013(3) 0.008(3) _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 C13 1.370(5) . ? O1 C12 1.423(5) . ? O2 C2 1.373(5) . ? O2 C1 1.437(5) . ? O2 H7 0.9800 . ? O2 H6 0.9800 . ? O3 C21 1.357(5) . ? O3 C22 1.399(5) . ? O4 C23 1.222(5) . ? N2 C4 1.369(5) . ? N2 C5 1.387(5) . ? N2 H8 0.85(4) . ? N3 C6 1.342(5) . ? N3 N14 1.355(5) . ? N3 C7 1.447(5) . ? C1 H5 0.9700 . ? C1 H4 0.9700 . ? C1 H1 0.9700 . ? C2 C3 1.387(6) . ? C2 C13 1.397(6) . ? C3 C4 1.407(6) . ? C3 C23 1.454(6) . ? C4 C20 1.399(5) . ? C5 C19 1.364(5) . ? C5 C6 1.445(6) . ? C6 N16 1.327(5) . ? C7 C8 1.518(6) . ? C7 H12 0.9800 . ? C7 H11 0.9800 . ? C8 C17 1.375(5) . ? C8 C9 1.379(6) . ? C9 C10 1.393(6) . ? C9 H16 0.9400 . ? N16 N15 1.369(5) . ? C10 C11 1.374(6) . ? C10 H15 0.9400 . ? N15 N14 1.286(5) . ? C11 C18 1.368(6) . ? C11 H2 0.9400 . ? C12 H3 0.9700 . ? C12 H22 0.9700 . ? C12 H23 0.9700 . ? C13 C21 1.402(6) . ? C17 C18 1.390(6) . ? C17 H13 0.9400 . ? C18 H14 0.9400 . ? C19 C20 1.425(6) . ? C19 H20 0.9400 . ? C20 C21 1.408(6) . ? C22 H19 0.9700 . ? C22 H17 0.9700 . ? C22 H18 0.9700 . ? C23 H21 0.9400 . ? 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 O1 C12 117.4(3) . . ? C2 O2 C1 115.1(3) . . ? C2 O2 H7 108.5 . . ? C1 O2 H7 108.5 . . ? C2 O2 H6 108.5 . . ? C1 O2 H6 108.5 . . ? H7 O2 H6 107.5 . . ? C21 O3 C22 119.1(3) . . ? C4 N2 C5 108.9(4) . . ? C4 N2 H8 126(3) . . ? C5 N2 H8 125(3) . . ? C6 N3 N14 107.8(3) . . ? C6 N3 C7 131.7(4) . . ? N14 N3 C7 120.5(4) . . ? O2 C1 H5 109.5 . . ? O2 C1 H4 109.5 . . ? H5 C1 H4 109.5 . . ? O2 C1 H1 109.5 . . ? H5 C1 H1 109.5 . . ? H4 C1 H1 109.5 . . ? O2 C2 C3 118.8(4) . . ? O2 C2 C13 118.1(4) . . ? C3 C2 C13 123.1(4) . . ? C2 C3 C4 115.7(4) . . ? C2 C3 C23 123.9(4) . . ? C4 C3 C23 120.2(4) . . ? N2 C4 C20 107.6(4) . . ? N2 C4 C3 128.5(4) . . ? C20 C4 C3 123.7(4) . . ? C19 C5 N2 109.0(4) . . ? C19 C5 C6 132.7(4) . . ? N2 C5 C6 118.3(4) . . ? N16 C6 N3 108.8(4) . . ? N16 C6 C5 124.5(4) . . ? N3 C6 C5 126.7(4) . . ? N3 C7 C8 112.5(3) . . ? N3 C7 H12 109.1 . . ? C8 C7 H12 109.1 . . ? N3 C7 H11 109.1 . . ? C8 C7 H11 109.1 . . ? H12 C7 H11 107.8 . . ? C17 C8 C9 118.8(4) . . ? C17 C8 C7 121.2(4) . . ? C9 C8 C7 119.9(4) . . ? C8 C9 C10 121.0(4) . . ? C8 C9 H16 119.5 . . ? C10 C9 H16 119.5 . . ? C6 N16 N15 105.5(3) . . ? C11 C10 C9 119.5(5) . . ? C11 C10 H15 120.3 . . ? C9 C10 H15 120.3 . . ? N14 N15 N16 110.7(4) . . ? C18 C11 C10 119.8(4) . . ? C18 C11 H2 120.1 . . ? C10 C11 H2 120.1 . . ? O1 C12 H3 109.5 . . ? O1 C12 H22 109.5 . . ? H3 C12 H22 109.5 . . ? O1 C12 H23 109.5 . . ? H3 C12 H23 109.5 . . ? H22 C12 H23 109.5 . . ? O1 C13 C2 121.3(4) . . ? O1 C13 C21 118.8(4) . . ? C2 C13 C21 119.7(4) . . ? N15 N14 N3 107.2(4) . . ? C8 C17 C18 120.1(4) . . ? C8 C17 H13 119.9 . . ? C18 C17 H13 119.9 . . ? C11 C18 C17 120.8(4) . . ? C11 C18 H14 119.6 . . ? C17 C18 H14 119.6 . . ? C5 C19 C20 107.1(4) . . ? C5 C19 H20 126.5 . . ? C20 C19 H20 126.5 . . ? C4 C20 C21 118.3(4) . . ? C4 C20 C19 107.3(4) . . ? C21 C20 C19 134.2(4) . . ? O3 C21 C13 116.8(4) . . ? O3 C21 C20 123.6(4) . . ? C13 C21 C20 119.5(4) . . ? O3 C22 H19 109.5 . . ? O3 C22 H17 109.5 . . ? H19 C22 H17 109.5 . . ? O3 C22 H18 109.5 . . ? H19 C22 H18 109.5 . . ? H17 C22 H18 109.5 . . ? O4 C23 C3 124.3(5) . . ? O4 C23 H21 117.9 . . ? C3 C23 H21 117.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O2 C2 C3 -107.0(4) . . . . ? C1 O2 C2 C13 73.0(5) . . . . ? O2 C2 C3 C4 177.8(3) . . . . ? C13 C2 C3 C4 -2.2(6) . . . . ? O2 C2 C3 C23 2.2(6) . . . . ? C13 C2 C3 C23 -177.8(4) . . . . ? C5 N2 C4 C20 -0.6(4) . . . . ? C5 N2 C4 C3 175.3(4) . . . . ? C2 C3 C4 N2 -173.0(4) . . . . ? C23 C3 C4 N2 2.7(6) . . . . ? C2 C3 C4 C20 2.3(6) . . . . ? C23 C3 C4 C20 178.1(4) . . . . ? C4 N2 C5 C19 0.9(4) . . . . ? C4 N2 C5 C6 -177.2(3) . . . . ? N14 N3 C6 N16 -0.6(4) . . . . ? C7 N3 C6 N16 -178.9(3) . . . . ? N14 N3 C6 C5 -179.8(4) . . . . ? C7 N3 C6 C5 1.9(6) . . . . ? C19 C5 C6 N16 176.5(4) . . . . ? N2 C5 C6 N16 -5.9(6) . . . . ? C19 C5 C6 N3 -4.3(7) . . . . ? N2 C5 C6 N3 173.2(3) . . . . ? C6 N3 C7 C8 79.7(5) . . . . ? N14 N3 C7 C8 -98.4(4) . . . . ? N3 C7 C8 C17 32.3(5) . . . . ? N3 C7 C8 C9 -150.7(4) . . . . ? C17 C8 C9 C10 2.2(6) . . . . ? C7 C8 C9 C10 -174.9(4) . . . . ? N3 C6 N16 N15 0.7(4) . . . . ? C5 C6 N16 N15 179.9(4) . . . . ? C8 C9 C10 C11 -1.2(6) . . . . ? C6 N16 N15 N14 -0.5(4) . . . . ? C9 C10 C11 C18 0.2(6) . . . . ? C12 O1 C13 C2 78.1(5) . . . . ? C12 O1 C13 C21 -106.7(4) . . . . ? O2 C2 C13 O1 -4.9(5) . . . . ? C3 C2 C13 O1 175.1(4) . . . . ? O2 C2 C13 C21 179.9(3) . . . . ? C3 C2 C13 C21 0.0(6) . . . . ? N16 N15 N14 N3 0.2(4) . . . . ? C6 N3 N14 N15 0.2(4) . . . . ? C7 N3 N14 N15 178.8(3) . . . . ? C9 C8 C17 C18 -2.1(6) . . . . ? C7 C8 C17 C18 174.9(4) . . . . ? C10 C11 C18 C17 -0.1(7) . . . . ? C8 C17 C18 C11 1.1(6) . . . . ? N2 C5 C19 C20 -0.8(4) . . . . ? C6 C5 C19 C20 176.9(4) . . . . ? N2 C4 C20 C21 176.1(3) . . . . ? C3 C4 C20 C21 -0.1(6) . . . . ? N2 C4 C20 C19 0.1(4) . . . . ? C3 C4 C20 C19 -176.1(4) . . . . ? C5 C19 C20 C4 0.5(4) . . . . ? C5 C19 C20 C21 -174.6(4) . . . . ? C22 O3 C21 C13 137.3(4) . . . . ? C22 O3 C21 C20 -46.9(6) . . . . ? O1 C13 C21 O3 3.0(5) . . . . ? C2 C13 C21 O3 178.3(3) . . . . ? O1 C13 C21 C20 -172.9(3) . . . . ? C2 C13 C21 C20 2.4(6) . . . . ? C4 C20 C21 O3 -177.9(3) . . . . ? C19 C20 C21 O3 -3.3(7) . . . . ? C4 C20 C21 C13 -2.3(6) . . . . ? C19 C20 C21 C13 172.4(4) . . . . ? C2 C3 C23 O4 174.7(4) . . . . ? C4 C3 C23 O4 -0.7(6) . . . . ? _refine_diff_density_max 0.212 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.058 _shelx_res_file ; TITL LXF_182_0ma_a.res in P2(1)/c LXF_182_0ma.res created by SHELXL-2018/3 at 15:58:05 on 31-Mar-2021 CELL 1.54178 9.5268 25.0880 8.4177 90.000 111.280 90.000 ZERR 4.00 0.0003 0.0008 0.0003 0.000 0.002 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H N O UNIT 80 84 20 16 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -58.160 ACTA L.S. 4 FMAP 2 PLAN -5 0 0.00 HTAB BOND $H CONF WGHT 0.100000 FVAR 0.41037 O1 4 0.100180 0.366536 0.866076 11.00000 0.04922 0.06904 = 0.04212 0.00056 0.01296 -0.01059 O2 4 0.397723 0.334915 0.995515 11.00000 0.04789 0.08051 = 0.06014 0.01749 0.01779 0.00546 AFIX 23 H7 2 0.350990 0.332352 1.081518 11.00000 -1.20000 H6 2 0.507106 0.333268 1.055381 11.00000 -1.20000 AFIX 0 O3 4 0.022362 0.461894 0.718256 11.00000 0.03218 0.05890 = 0.07399 -0.00296 0.00929 0.00041 O4 4 0.732141 0.422908 0.928312 11.00000 0.04023 0.08767 = 0.05768 0.00388 0.01707 0.00375 N2 3 0.515213 0.498561 0.760780 11.00000 0.03243 0.06045 = 0.04278 -0.00553 0.01006 0.00113 H8 2 0.610031 0.497071 0.785258 11.00000 0.04483 N3 3 0.412090 0.618408 0.486551 11.00000 0.03544 0.05338 = 0.04019 -0.00077 0.01374 -0.00442 C1 1 0.351832 0.289588 0.884305 11.00000 0.08929 0.05181 = 0.10023 -0.00291 0.03451 -0.00312 AFIX 137 H5 2 0.243815 0.290888 0.822987 11.00000 -1.50000 H4 2 0.377606 0.257116 0.951230 11.00000 -1.50000 H1 2 0.403088 0.290152 0.803603 11.00000 -1.50000 AFIX 0 C2 1 0.361982 0.383594 0.916469 11.00000 0.04567 0.05033 = 0.03385 0.00845 0.00902 0.00747 C3 1 0.476333 0.414432 0.898819 11.00000 0.03891 0.05805 = 0.03712 -0.00217 0.01272 0.00461 C4 1 0.430821 0.462940 0.811324 11.00000 0.03848 0.05262 = 0.03472 -0.00618 0.01160 -0.00144 C5 1 0.421819 0.538755 0.666790 11.00000 0.03907 0.05029 = 0.03780 -0.00560 0.00577 0.00327 C6 1 0.486654 0.579624 0.593682 11.00000 0.03855 0.05032 = 0.03802 -0.00613 0.00935 -0.00142 C7 1 0.253894 0.632215 0.417176 11.00000 0.04438 0.05106 = 0.03964 -0.00052 0.01205 0.00257 AFIX 23 H12 2 0.194033 0.599481 0.385483 11.00000 -1.20000 H11 2 0.233843 0.653421 0.313482 11.00000 -1.20000 AFIX 0 C8 1 0.204711 0.663560 0.542312 11.00000 0.03892 0.04947 = 0.03158 0.00421 0.01061 0.00040 C9 1 0.058324 0.659671 0.535743 11.00000 0.04533 0.05877 = 0.03891 -0.00277 0.01231 -0.00533 AFIX 43 H16 2 -0.007850 0.635407 0.459876 11.00000 -1.20000 AFIX 0 N16 3 0.632545 0.584095 0.621669 11.00000 0.03953 0.06740 = 0.04852 -0.00392 0.01083 -0.00459 C10 1 0.006996 0.691133 0.639768 11.00000 0.04388 0.07077 = 0.05004 0.00091 0.01828 0.00171 AFIX 43 H15 2 -0.093577 0.688633 0.632593 11.00000 -1.20000 AFIX 0 N15 3 0.644808 0.627496 0.529062 11.00000 0.04746 0.07218 = 0.05699 0.00218 0.01703 -0.00816 C11 1 0.104560 0.725855 0.752964 11.00000 0.05319 0.06527 = 0.05028 -0.01101 0.01716 -0.00536 AFIX 43 H2 2 0.071089 0.747201 0.823931 11.00000 -1.20000 AFIX 0 C12 1 0.084625 0.360947 1.027169 11.00000 0.06701 0.10157 = 0.04987 -0.00454 0.02552 -0.01295 AFIX 137 H3 2 0.168572 0.340459 1.103032 11.00000 -1.50000 H22 2 -0.008964 0.342643 1.012419 11.00000 -1.50000 H23 2 0.083667 0.395932 1.075829 11.00000 -1.50000 AFIX 0 C13 1 0.211395 0.399718 0.857559 11.00000 0.03622 0.06425 = 0.03756 -0.00397 0.01040 -0.00494 N14 3 0.514563 0.648011 0.448365 11.00000 0.04183 0.06918 = 0.04929 -0.00151 0.01630 -0.00709 C17 1 0.301680 0.697877 0.658045 11.00000 0.04374 0.05777 = 0.04084 0.00034 0.01297 0.00103 AFIX 43 H13 2 0.402733 0.700128 0.666874 11.00000 -1.20000 AFIX 0 C18 1 0.250543 0.729246 0.762013 11.00000 0.04997 0.05632 = 0.04900 -0.01068 0.00957 -0.01016 AFIX 43 H14 2 0.317064 0.753065 0.839430 11.00000 -1.20000 AFIX 0 C19 1 0.278488 0.529398 0.659216 11.00000 0.03558 0.05351 = 0.04703 0.00041 0.00714 0.00418 AFIX 43 H20 2 0.193528 0.550754 0.604545 11.00000 -1.20000 AFIX 0 C20 1 0.281837 0.481143 0.749809 11.00000 0.03345 0.05124 = 0.04421 -0.00399 0.01298 0.00231 C21 1 0.170919 0.449200 0.776481 11.00000 0.03154 0.06086 = 0.04238 -0.00421 0.00897 0.00089 C22 1 -0.020491 0.513637 0.743117 11.00000 0.05220 0.08676 = 0.10110 -0.03264 0.02296 0.00174 AFIX 137 H19 2 0.057975 0.529726 0.839627 11.00000 -1.50000 H17 2 -0.113494 0.512308 0.765276 11.00000 -1.50000 H18 2 -0.035663 0.534750 0.641684 11.00000 -1.50000 AFIX 0 C23 1 0.632783 0.397613 0.953927 11.00000 0.05284 0.06895 = 0.04561 -0.00242 0.01298 0.00776 AFIX 43 H21 2 0.659256 0.365162 1.013134 11.00000 -1.20000 REM ##### REM ##### REM ##### AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM LXF_182_0ma_a.res in P2(1)/c REM wR2 = 0.193400, GooF = S = 1.43511, Restrained GooF = 1.43511 for all data REM R1 = 0.065607 for 1606 Fo > 4sig(Fo) and 0.082172 for all 1965 data REM 269 parameters refined using 0 restraints END WGHT 0.0836 2.7793 REM Instructions for potential hydrogen bonds HTAB N2 O4 HTAB C1 O1 EQIV $1 -x, -y+1, -z+1 HTAB C7 O3_$1 HTAB C12 O2 EQIV $2 -x+1, -y+1, -z+2 HTAB C22 O4_$2 REM Highest difference peak 0.212, deepest hole -0.435, 1-sigma level 0.058 Q1 1 -0.0328 0.4931 0.8630 11.00000 0.05 0.21 Q2 1 0.2757 0.7927 0.8005 11.00000 0.05 0.18 Q3 1 0.2530 0.6848 0.3025 11.00000 0.05 0.17 Q4 1 0.0375 0.5473 0.7804 11.00000 0.05 0.17 Q5 1 0.0054 0.3239 0.6787 11.00000 0.05 0.17 ; _shelx_res_checksum 42109