# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2020 ####################################################################### # # 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_180530j _database_code_depnum_ccdc_archive 'CCDC 1938560' loop_ _audit_author_name _audit_author_address 'Rao jiarui' ;Guizhou University China ; _audit_update_record ; 2019-07-05 deposited with the CCDC. 2019-12-18 downloaded from the CCDC. ; _audit_creation_date 2019-07-05 _audit_creation_method ; Olex2 1.3-alpha (compiled 2019.03.18 svn.r3573 for OlexSys, GUI svn.r5794) ; _shelx_SHELXL_version_number 2014/7 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H22 N2 O3' _chemical_formula_sum 'C19 H22 N2 O3' _chemical_formula_weight 326.38 _chemical_melting_point ? 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' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' 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 7.2797(5) _cell_length_b 14.3957(12) _cell_length_c 32.249(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3379.5(5) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2321 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 21.436 _cell_measurement_theta_min 2.527 _shelx_estimated_absorpt_T_max 0.966 _shelx_estimated_absorpt_T_min 0.962 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.9659 _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_absorpt_special_details ? _exptl_crystal_colour brown _exptl_crystal_colour_primary brown _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1392 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_unetI/netI 0.0788 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 15106 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.017 _diffrn_reflns_theta_max 25.017 _diffrn_reflns_theta_min 2.526 _diffrn_ambient_temperature 298.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source ? _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1701 _reflns_number_total 2987 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.265 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.046 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 2987 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1155 _refine_ls_R_factor_gt 0.0549 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+3.0480P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1263 _refine_ls_wR_factor_ref 0.1557 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C10(H10) 2.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C9(H9A,H9B), C11(H11A,H11B) 2.c Aromatic/amide H refined with riding coordinates: N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C16(H16), C17(H17) 2.d Idealised Me refined as rotating group: C18(H18A,H18B,H18C), C19(H19A,H19B,H19C) 2.e Idealised tetrahedral OH refined as rotating group: O3(H3) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary ? _atom_sites_solution_secondary ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.1619(3) 0.34995(16) 0.15090(7) 0.0395(6) Uani 1 1 d . . . . . N2 N 0.5962(4) 0.17457(19) 0.19110(9) 0.0616(8) Uani 1 1 d . . . . . H2 H 0.6640 0.1631 0.2123 0.074 Uiso 1 1 calc R . . . . O1 O 0.3635(3) 0.43517(15) 0.08960(7) 0.0558(6) Uani 1 1 d . . . . . O2 O 0.2391(3) 0.46843(14) 0.19368(7) 0.0603(7) Uani 1 1 d . . . . . O3 O 0.2080(4) 0.14921(15) 0.21968(7) 0.0668(8) Uani 1 1 d . . . . . H3 H 0.2287 0.0953 0.2129 0.100 Uiso 1 1 calc GR . . . . C1 C 0.2273(4) 0.4363(2) 0.15847(10) 0.0427(8) Uani 1 1 d . . . . . C2 C 0.2864(5) 0.4909(2) 0.12155(10) 0.0483(8) Uani 1 1 d . . . . . H2A H 0.1812 0.5241 0.1105 0.058 Uiso 1 1 calc R . . . . H2B H 0.3765 0.5367 0.1302 0.058 Uiso 1 1 calc R . . . . C3 C 0.2572(4) 0.3601(2) 0.07941(9) 0.0434(7) Uani 1 1 d . . . . . C4 C 0.1519(4) 0.31705(19) 0.10941(9) 0.0373(7) Uani 1 1 d . . . . . C5 C 0.0480(4) 0.2403(2) 0.09838(10) 0.0500(8) Uani 1 1 d . . . . . H5 H -0.0282 0.2121 0.1178 0.060 Uiso 1 1 calc R . . . . C6 C 0.0578(5) 0.2057(2) 0.05847(11) 0.0625(10) Uani 1 1 d . . . . . H6 H -0.0107 0.1536 0.0512 0.075 Uiso 1 1 calc R . . . . C7 C 0.1677(5) 0.2476(3) 0.02949(11) 0.0663(11) Uani 1 1 d . . . . . H7 H 0.1764 0.2231 0.0029 0.080 Uiso 1 1 calc R . . . . C8 C 0.2644(5) 0.3254(2) 0.03985(10) 0.0574(9) Uani 1 1 d . . . . . H8 H 0.3357 0.3552 0.0199 0.069 Uiso 1 1 calc R . . . . C9 C 0.1218(4) 0.2874(2) 0.18550(9) 0.0450(8) Uani 1 1 d . . . . . H9A H 0.0001 0.2611 0.1820 0.054 Uiso 1 1 calc R . . . . H9B H 0.1236 0.3220 0.2113 0.054 Uiso 1 1 calc R . . . . C10 C 0.2630(4) 0.2096(2) 0.18739(9) 0.0435(8) Uani 1 1 d . . . . . H10 H 0.2600 0.1753 0.1611 0.052 Uiso 1 1 calc R . . . . C11 C 0.4566(5) 0.2459(2) 0.19429(10) 0.0529(9) Uani 1 1 d . . . . . H11A H 0.4820 0.2940 0.1740 0.064 Uiso 1 1 calc R . . . . H11B H 0.4634 0.2740 0.2216 0.064 Uiso 1 1 calc R . . . . C12 C 0.6241(4) 0.1244(2) 0.15517(10) 0.0457(8) Uani 1 1 d . . . . . C13 C 0.6989(4) 0.0346(2) 0.15752(10) 0.0474(8) Uani 1 1 d . . . . . C14 C 0.7251(4) -0.0138(2) 0.12082(11) 0.0548(9) Uani 1 1 d . . . . . H14 H 0.7748 -0.0732 0.1224 0.066 Uiso 1 1 calc R . . . . C15 C 0.6817(4) 0.0207(3) 0.08218(11) 0.0584(9) Uani 1 1 d . . . . . C16 C 0.6094(4) 0.1089(3) 0.08078(11) 0.0581(9) Uani 1 1 d . . . . . H16 H 0.5790 0.1346 0.0552 0.070 Uiso 1 1 calc R . . . . C17 C 0.5808(4) 0.1601(2) 0.11632(10) 0.0525(9) Uani 1 1 d . . . . . H17 H 0.5317 0.2196 0.1143 0.063 Uiso 1 1 calc R . . . . C18 C 0.7460(5) -0.0075(3) 0.19855(10) 0.0661(10) Uani 1 1 d . . . . . H18A H 0.7862 -0.0704 0.1946 0.099 Uiso 1 1 calc GR . . . . H18B H 0.6396 -0.0069 0.2161 0.099 Uiso 1 1 calc GR . . . . H18C H 0.8426 0.0278 0.2113 0.099 Uiso 1 1 calc GR . . . . C19 C 0.7113(6) -0.0362(3) 0.04335(12) 0.0834(13) Uani 1 1 d . . . . . H19A H 0.8389 -0.0346 0.0358 0.125 Uiso 1 1 calc GR . . . . H19B H 0.6389 -0.0109 0.0212 0.125 Uiso 1 1 calc GR . . . . H19C H 0.6749 -0.0993 0.0484 0.125 Uiso 1 1 calc GR . . . . 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 0.0449(15) 0.0347(13) 0.0390(14) 0.0000(11) -0.0013(12) 0.0004(11) N2 0.068(2) 0.0623(18) 0.0544(18) -0.0089(15) -0.0234(15) 0.0199(16) O1 0.0518(14) 0.0550(14) 0.0606(15) -0.0070(11) 0.0117(11) -0.0118(11) O2 0.0902(18) 0.0399(12) 0.0507(15) -0.0063(11) -0.0118(13) 0.0033(12) O3 0.116(2) 0.0383(12) 0.0458(13) 0.0055(10) 0.0250(14) 0.0086(14) C1 0.0449(18) 0.0341(17) 0.049(2) -0.0019(15) -0.0076(15) 0.0068(14) C2 0.054(2) 0.0361(17) 0.055(2) -0.0013(15) 0.0005(17) -0.0024(15) C3 0.0391(17) 0.0456(18) 0.0455(19) -0.0025(15) -0.0012(15) -0.0016(14) C4 0.0388(17) 0.0377(16) 0.0353(17) -0.0002(13) -0.0056(14) -0.0004(13) C5 0.050(2) 0.051(2) 0.049(2) -0.0009(16) -0.0051(16) -0.0127(16) C6 0.071(3) 0.062(2) 0.055(2) -0.0128(18) -0.013(2) -0.014(2) C7 0.074(3) 0.082(3) 0.043(2) -0.0141(19) -0.0053(19) 0.002(2) C8 0.060(2) 0.066(2) 0.046(2) 0.0012(17) 0.0075(17) -0.0043(19) C9 0.053(2) 0.0421(17) 0.0396(17) 0.0002(14) 0.0075(15) 0.0017(15) C10 0.062(2) 0.0349(16) 0.0336(16) -0.0016(13) 0.0026(15) 0.0023(15) C11 0.063(2) 0.0406(17) 0.055(2) -0.0066(16) -0.0171(17) 0.0063(16) C12 0.0403(18) 0.0472(19) 0.050(2) -0.0025(16) -0.0030(15) 0.0002(15) C13 0.0383(18) 0.054(2) 0.050(2) 0.0019(16) -0.0005(15) 0.0029(15) C14 0.0388(19) 0.064(2) 0.061(2) -0.0012(18) 0.0037(17) 0.0057(16) C15 0.0389(19) 0.085(3) 0.052(2) -0.006(2) 0.0089(16) -0.0021(18) C16 0.0432(19) 0.085(3) 0.046(2) 0.0108(19) 0.0057(16) -0.0071(19) C17 0.0444(19) 0.060(2) 0.053(2) 0.0069(18) 0.0027(17) 0.0015(16) C18 0.073(2) 0.062(2) 0.063(2) 0.0031(18) -0.014(2) 0.021(2) C19 0.068(3) 0.118(3) 0.064(3) -0.024(2) 0.009(2) 0.001(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 N1 C1 1.354(4) . ? N1 C4 1.422(3) . ? N1 C9 1.463(3) . ? N2 H2 0.8600 . ? N2 C11 1.449(4) . ? N2 C12 1.380(4) . ? O1 C2 1.422(4) . ? O1 C3 1.370(3) . ? O2 C1 1.229(3) . ? O3 H3 0.8200 . ? O3 C10 1.414(3) . ? C1 C2 1.490(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.381(4) . ? C3 C8 1.371(4) . ? C4 C5 1.385(4) . ? C5 H5 0.9300 . ? C5 C6 1.382(4) . ? C6 H6 0.9300 . ? C6 C7 1.370(5) . ? C7 H7 0.9300 . ? C7 C8 1.365(5) . ? C8 H8 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.521(4) . ? C10 H10 0.9800 . ? C10 C11 1.520(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.405(4) . ? C12 C17 1.391(4) . ? C13 C14 1.387(4) . ? C13 C18 1.495(4) . ? C14 H14 0.9300 . ? C14 C15 1.378(5) . ? C15 C16 1.375(5) . ? C15 C19 1.512(5) . ? C16 H16 0.9300 . ? C16 C17 1.379(5) . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 119.6(2) . . ? C1 N1 C9 119.9(2) . . ? C4 N1 C9 120.2(2) . . ? C11 N2 H2 118.9 . . ? C12 N2 H2 118.9 . . ? C12 N2 C11 122.3(3) . . ? C3 O1 C2 113.4(2) . . ? C10 O3 H3 109.5 . . ? N1 C1 C2 116.2(3) . . ? O2 C1 N1 122.4(3) . . ? O2 C1 C2 121.3(3) . . ? O1 C2 C1 113.3(2) . . ? O1 C2 H2A 108.9 . . ? O1 C2 H2B 108.9 . . ? C1 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? O1 C3 C4 120.0(3) . . ? O1 C3 C8 119.3(3) . . ? C8 C3 C4 120.7(3) . . ? C3 C4 N1 118.8(3) . . ? C3 C4 C5 118.7(3) . . ? C5 C4 N1 122.4(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5 120.0 . . ? C5 C6 H6 119.8 . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6 119.8 . . ? C6 C7 H7 120.2 . . ? C8 C7 C6 119.7(3) . . ? C8 C7 H7 120.2 . . ? C3 C8 H8 119.8 . . ? C7 C8 C3 120.5(3) . . ? C7 C8 H8 119.8 . . ? N1 C9 H9A 109.6 . . ? N1 C9 H9B 109.6 . . ? N1 C9 C10 110.4(2) . . ? H9A C9 H9B 108.1 . . ? C10 C9 H9A 109.6 . . ? C10 C9 H9B 109.6 . . ? O3 C10 C9 106.9(2) . . ? O3 C10 H10 108.7 . . ? O3 C10 C11 111.5(3) . . ? C9 C10 H10 108.7 . . ? C11 C10 C9 112.2(2) . . ? C11 C10 H10 108.7 . . ? N2 C11 C10 113.3(3) . . ? N2 C11 H11A 108.9 . . ? N2 C11 H11B 108.9 . . ? C10 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? N2 C12 C13 119.6(3) . . ? N2 C12 C17 121.9(3) . . ? C17 C12 C13 118.5(3) . . ? C12 C13 C18 120.6(3) . . ? C14 C13 C12 118.0(3) . . ? C14 C13 C18 121.3(3) . . ? C13 C14 H14 118.0 . . ? C15 C14 C13 124.0(3) . . ? C15 C14 H14 118.0 . . ? C14 C15 C19 121.4(4) . . ? C16 C15 C14 116.8(3) . . ? C16 C15 C19 121.8(4) . . ? C15 C16 H16 119.2 . . ? C15 C16 C17 121.6(3) . . ? C17 C16 H16 119.2 . . ? C12 C17 H17 119.4 . . ? C16 C17 C12 121.1(3) . . ? C16 C17 H17 119.4 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 O1 -33.7(4) . . . . ? N1 C4 C5 C6 -173.5(3) . . . . ? N1 C9 C10 O3 -176.2(2) . . . . ? N1 C9 C10 C11 61.2(3) . . . . ? N2 C12 C13 C14 180.0(3) . . . . ? N2 C12 C13 C18 0.8(5) . . . . ? N2 C12 C17 C16 -179.9(3) . . . . ? O1 C3 C4 N1 -2.4(4) . . . . ? O1 C3 C4 C5 -179.0(3) . . . . ? O1 C3 C8 C7 176.4(3) . . . . ? O2 C1 C2 O1 145.8(3) . . . . ? O3 C10 C11 N2 67.3(3) . . . . ? C1 N1 C4 C3 19.4(4) . . . . ? C1 N1 C4 C5 -164.1(3) . . . . ? C1 N1 C9 C10 -108.5(3) . . . . ? C2 O1 C3 C4 -32.4(4) . . . . ? C2 O1 C3 C8 151.1(3) . . . . ? C3 O1 C2 C1 49.8(4) . . . . ? C3 C4 C5 C6 3.0(5) . . . . ? C4 N1 C1 O2 180.0(3) . . . . ? C4 N1 C1 C2 -0.5(4) . . . . ? C4 N1 C9 C10 64.5(3) . . . . ? C4 C3 C8 C7 -0.1(5) . . . . ? C4 C5 C6 C7 -0.9(5) . . . . ? C5 C6 C7 C8 -1.7(6) . . . . ? C6 C7 C8 C3 2.2(5) . . . . ? C8 C3 C4 N1 174.1(3) . . . . ? C8 C3 C4 C5 -2.5(5) . . . . ? C9 N1 C1 O2 -6.9(4) . . . . ? C9 N1 C1 C2 172.6(3) . . . . ? C9 N1 C4 C3 -153.6(3) . . . . ? C9 N1 C4 C5 22.8(4) . . . . ? C9 C10 C11 N2 -172.8(3) . . . . ? C11 N2 C12 C13 -153.3(3) . . . . ? C11 N2 C12 C17 26.8(5) . . . . ? C12 N2 C11 C10 60.9(4) . . . . ? C12 C13 C14 C15 -0.2(5) . . . . ? C13 C12 C17 C16 0.3(5) . . . . ? C13 C14 C15 C16 0.4(5) . . . . ? C13 C14 C15 C19 -179.2(3) . . . . ? C14 C15 C16 C17 -0.3(5) . . . . ? C15 C16 C17 C12 0.0(5) . . . . ? C17 C12 C13 C14 -0.2(5) . . . . ? C17 C12 C13 C18 -179.3(3) . . . . ? C18 C13 C14 C15 179.0(3) . . . . ? C19 C15 C16 C17 179.3(3) . . . . ? _shelx_res_file ; 180530j.res created by SHELXL-2014/7 TITL 180530j in Pbca CELL 0.71073 7.2797 14.3957 32.2487 90 90 90 ZERR 8 0.0005 0.0012 0.0027 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 152 176 16 24 L.S. 16 PLAN 1 SIZE 0.4 0.41 0.45 TEMP 25 BOND $h htab conf fmap 2 acta OMIT -1 50.04 REM REM REM WGHT 0.023100 3.048000 FVAR 0.30134 N1 3 0.161936 0.349951 0.150905 11.00000 0.04493 0.03469 = 0.03895 -0.00004 -0.00128 0.00039 N2 3 0.596172 0.174569 0.191101 11.00000 0.06792 0.06232 = 0.05445 -0.00887 -0.02339 0.01992 AFIX 43 H2 2 0.663972 0.163067 0.212328 11.00000 -1.20000 AFIX 0 O1 4 0.363519 0.435171 0.089596 11.00000 0.05177 0.05498 = 0.06056 -0.00696 0.01165 -0.01183 O2 4 0.239105 0.468428 0.193680 11.00000 0.09021 0.03993 = 0.05070 -0.00628 -0.01181 0.00331 O3 4 0.207965 0.149206 0.219684 11.00000 0.11608 0.03834 = 0.04583 0.00553 0.02500 0.00859 AFIX 147 H3 2 0.228714 0.095309 0.212920 11.00000 -1.50000 AFIX 0 C1 1 0.227345 0.436342 0.158467 11.00000 0.04493 0.03410 = 0.04905 -0.00189 -0.00761 0.00678 C2 1 0.286432 0.490945 0.121554 11.00000 0.05400 0.03614 = 0.05463 -0.00128 0.00052 -0.00240 AFIX 23 H2A 2 0.181207 0.524114 0.110541 11.00000 -1.20000 H2B 2 0.376518 0.536682 0.130177 11.00000 -1.20000 AFIX 0 C3 1 0.257188 0.360060 0.079414 11.00000 0.03909 0.04564 = 0.04547 -0.00254 -0.00115 -0.00160 C4 1 0.151942 0.317049 0.109405 11.00000 0.03882 0.03770 = 0.03529 -0.00019 -0.00560 -0.00039 C5 1 0.048045 0.240320 0.098377 11.00000 0.04981 0.05120 = 0.04900 -0.00085 -0.00512 -0.01268 AFIX 43 H5 2 -0.028177 0.212140 0.117803 11.00000 -1.20000 AFIX 0 C6 1 0.057803 0.205696 0.058465 11.00000 0.07139 0.06158 = 0.05461 -0.01277 -0.01337 -0.01401 AFIX 43 H6 2 -0.010678 0.153622 0.051232 11.00000 -1.20000 AFIX 0 C7 1 0.167697 0.247585 0.029486 11.00000 0.07368 0.08233 = 0.04281 -0.01407 -0.00526 0.00200 AFIX 43 H7 2 0.176357 0.223097 0.002871 11.00000 -1.20000 AFIX 0 C8 1 0.264408 0.325416 0.039853 11.00000 0.06030 0.06588 = 0.04603 0.00122 0.00754 -0.00426 AFIX 43 H8 2 0.335696 0.355151 0.019941 11.00000 -1.20000 AFIX 0 C9 1 0.121811 0.287374 0.185497 11.00000 0.05324 0.04209 = 0.03963 0.00018 0.00754 0.00173 AFIX 23 H9A 2 0.000057 0.261112 0.182047 11.00000 -1.20000 H9B 2 0.123583 0.322001 0.211297 11.00000 -1.20000 AFIX 0 C10 1 0.262987 0.209562 0.187394 11.00000 0.06194 0.03485 = 0.03358 -0.00164 0.00264 0.00226 AFIX 13 H10 2 0.259965 0.175306 0.161142 11.00000 -1.20000 AFIX 0 C11 1 0.456552 0.245936 0.194288 11.00000 0.06319 0.04055 = 0.05502 -0.00664 -0.01709 0.00632 AFIX 23 H11A 2 0.481980 0.293999 0.174003 11.00000 -1.20000 H11B 2 0.463394 0.274040 0.221582 11.00000 -1.20000 AFIX 0 C12 1 0.624138 0.124394 0.155171 11.00000 0.04033 0.04719 = 0.04966 -0.00250 -0.00301 0.00016 C13 1 0.698907 0.034598 0.157524 11.00000 0.03833 0.05376 = 0.04999 0.00187 -0.00047 0.00287 C14 1 0.725052 -0.013827 0.120819 11.00000 0.03880 0.06427 = 0.06137 -0.00119 0.00368 0.00572 AFIX 43 H14 2 0.774833 -0.073221 0.122373 11.00000 -1.20000 AFIX 0 C15 1 0.681745 0.020719 0.082180 11.00000 0.03890 0.08461 = 0.05159 -0.00585 0.00888 -0.00209 C16 1 0.609391 0.108885 0.080779 11.00000 0.04322 0.08535 = 0.04580 0.01077 0.00572 -0.00711 AFIX 43 H16 2 0.578991 0.134594 0.055228 11.00000 -1.20000 AFIX 0 C17 1 0.580789 0.160129 0.116322 11.00000 0.04440 0.05985 = 0.05329 0.00694 0.00269 0.00155 AFIX 43 H17 2 0.531680 0.219591 0.114278 11.00000 -1.20000 AFIX 0 C18 1 0.746041 -0.007470 0.198547 11.00000 0.07301 0.06189 = 0.06328 0.00313 -0.01410 0.02105 AFIX 137 H18A 2 0.786182 -0.070361 0.194558 11.00000 -1.50000 H18B 2 0.639589 -0.006867 0.216115 11.00000 -1.50000 H18C 2 0.842622 0.027801 0.211312 11.00000 -1.50000 AFIX 0 C19 1 0.711300 -0.036199 0.043345 11.00000 0.06788 0.11789 = 0.06436 -0.02397 0.00859 0.00118 AFIX 137 H19A 2 0.838862 -0.034554 0.035832 11.00000 -1.50000 H19B 2 0.638946 -0.010893 0.021169 11.00000 -1.50000 H19C 2 0.674855 -0.099289 0.048378 11.00000 -1.50000 AFIX 0 HKLF 4 REM 180530j in Pbca REM R1 = 0.0549 for 1701 Fo > 4sig(Fo) and 0.1155 for all 2987 data REM 220 parameters refined using 0 restraints END WGHT 0.0230 3.0481 REM Instructions for potential hydrogen bonds EQIV $1 x+1/2, y, -z+1/2 HTAB N2 O3_$1 EQIV $2 -x+1/2, y-1/2, z HTAB O3 O2_$2 REM Highest difference peak 0.265, deepest hole -0.201, 1-sigma level 0.046 Q1 1 0.5997 0.1268 0.2205 11.00000 0.05 0.27 ; _shelx_res_checksum 90236 _olex2_submission_special_instructions 'No special instructions were received'