# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2022 ####################################################################### # # 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_i18213 _database_code_depnum_ccdc_archive 'CCDC 2085356' loop_ _audit_author_name _audit_author_address 'Chieh-Kai Chan' 'Academia Sinica' _audit_update_record ; 2021-05-24 deposited with the CCDC. 2022-03-01 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 'C24 H17 N O2' _chemical_formula_sum 'C24 H17 N O2' _chemical_formula_weight 351.38 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' 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/n' _space_group_name_Hall '-P 2yn' _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+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.4058(2) _cell_length_b 12.1092(3) _cell_length_c 21.6453(7) _cell_angle_alpha 90 _cell_angle_beta 92.2490(10) _cell_angle_gamma 90 _cell_volume 1677.71(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 9884 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 27.11 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.391 _exptl_crystal_F_000 736 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.362 _exptl_crystal_size_mid 0.284 _exptl_crystal_size_min 0.090 _exptl_absorpt_coefficient_mu 0.089 _shelx_estimated_absorpt_T_min 0.969 _shelx_estimated_absorpt_T_max 0.992 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.888 _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 50975 _diffrn_reflns_av_unetI/netI 0.0239 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.927 _diffrn_reflns_theta_max 27.102 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_point_group_measured_fraction_full 0.997 _reflns_number_total 3704 _reflns_number_gt 3271 _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^)+(0.0446P)^2^+0.7291P] 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 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_extinction_coef 0.016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3704 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.91233(13) 0.66636(8) 0.51659(4) 0.0225(2) Uani 1 1 d . . . . . O2 O 1.25667(13) 0.60515(7) 0.52173(4) 0.0217(2) Uani 1 1 d . . . . . N1 N 0.61256(14) 0.62219(8) 0.17468(4) 0.0154(2) Uani 1 1 d . . . . . C1 C 0.78876(17) 0.56265(9) 0.18174(5) 0.0152(2) Uani 1 1 d . . . . . C2 C 0.90334(17) 0.55679(9) 0.23786(5) 0.0158(2) Uani 1 1 d . . . . . H2 H 1.024257 0.511480 0.241522 0.019 Uiso 1 1 calc R U . . . C3 C 0.83983(17) 0.61769(9) 0.28862(5) 0.0150(2) Uani 1 1 d . . . . . C4 C 0.65835(17) 0.68103(9) 0.28027(5) 0.0161(2) Uani 1 1 d . . . . . H4 H 0.610463 0.724818 0.313261 0.019 Uiso 1 1 calc R U . . . C5 C 0.54733(17) 0.67988(9) 0.22329(5) 0.0148(2) Uani 1 1 d . . . . . C6 C 0.85011(18) 0.49772(9) 0.12684(5) 0.0162(2) Uani 1 1 d . . . . . C7 C 0.69764(18) 0.46862(9) 0.08174(5) 0.0186(2) Uani 1 1 d . . . . . H7 H 0.558244 0.493892 0.085324 0.022 Uiso 1 1 calc R U . . . C8 C 0.7479(2) 0.40320(10) 0.03182(5) 0.0218(3) Uani 1 1 d . . . . . H8 H 0.643108 0.384663 0.001288 0.026 Uiso 1 1 calc R U . . . C9 C 0.9504(2) 0.36474(10) 0.02627(5) 0.0226(3) Uani 1 1 d . . . . . H9 H 0.983572 0.318186 -0.007281 0.027 Uiso 1 1 calc R U . . . C10 C 1.10416(19) 0.39478(10) 0.07010(5) 0.0211(3) Uani 1 1 d . . . . . H10 H 1.243316 0.369309 0.066254 0.025 Uiso 1 1 calc R U . . . C11 C 1.05519(18) 0.46207(9) 0.11966(5) 0.0180(2) Uani 1 1 d . . . . . H11 H 1.162031 0.483899 0.148814 0.022 Uiso 1 1 calc R U . . . C12 C 0.95796(17) 0.61387(9) 0.34924(5) 0.0155(2) Uani 1 1 d . . . . . C13 C 1.16467(18) 0.57602(9) 0.35327(5) 0.0176(2) Uani 1 1 d . . . . . H13 H 1.229219 0.553644 0.316528 0.021 Uiso 1 1 calc R U . . . C14 C 1.27967(18) 0.56999(10) 0.40966(5) 0.0185(2) Uani 1 1 d . . . . . H14 H 1.419315 0.543442 0.411955 0.022 Uiso 1 1 calc R U . . . C15 C 1.18061(18) 0.60433(9) 0.46137(5) 0.0171(2) Uani 1 1 d . . . . . C16 C 0.97636(18) 0.64144(9) 0.45831(5) 0.0166(2) Uani 1 1 d . . . . . C17 C 0.86056(18) 0.64749(9) 0.40363(5) 0.0165(2) Uani 1 1 d . . . . . H17 H 0.720398 0.673280 0.402412 0.020 Uiso 1 1 calc R U . . . C18 C 1.09230(18) 0.65118(10) 0.55714(5) 0.0204(3) Uani 1 1 d . . . . . H18A H 1.058679 0.600607 0.591281 0.024 Uiso 1 1 calc R U . . . H18B H 1.137109 0.722872 0.575198 0.024 Uiso 1 1 calc R U . . . C19 C 0.34921(17) 0.74308(9) 0.21253(5) 0.0151(2) Uani 1 1 d . . . . . C20 C 0.25287(18) 0.79916(9) 0.26008(5) 0.0176(2) Uani 1 1 d . . . . . H20 H 0.314444 0.797461 0.300713 0.021 Uiso 1 1 calc R U . . . C21 C 0.06825(18) 0.85742(9) 0.24884(5) 0.0198(2) Uani 1 1 d . . . . . H21 H 0.004827 0.895077 0.281728 0.024 Uiso 1 1 calc R U . . . C22 C -0.02387(18) 0.86074(9) 0.18962(6) 0.0203(2) Uani 1 1 d . . . . . H22 H -0.149740 0.900734 0.181821 0.024 Uiso 1 1 calc R U . . . C23 C 0.07007(18) 0.80497(10) 0.14196(5) 0.0208(3) Uani 1 1 d . . . . . H23 H 0.008299 0.807114 0.101350 0.025 Uiso 1 1 calc R U . . . C24 C 0.25341(18) 0.74621(9) 0.15330(5) 0.0173(2) Uani 1 1 d . . . . . H24 H 0.314848 0.707552 0.120418 0.021 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 0.0215(4) 0.0337(5) 0.0121(4) -0.0015(3) -0.0025(3) 0.0066(4) O2 0.0202(4) 0.0302(5) 0.0144(4) -0.0021(3) -0.0041(3) 0.0040(3) N1 0.0156(5) 0.0161(4) 0.0143(4) 0.0006(3) 0.0001(3) -0.0009(4) C1 0.0158(5) 0.0142(5) 0.0156(5) 0.0008(4) 0.0010(4) -0.0020(4) C2 0.0156(5) 0.0156(5) 0.0162(5) 0.0015(4) 0.0002(4) 0.0004(4) C3 0.0152(5) 0.0156(5) 0.0143(5) 0.0016(4) -0.0006(4) -0.0027(4) C4 0.0169(5) 0.0172(5) 0.0141(5) -0.0007(4) 0.0009(4) 0.0000(4) C5 0.0143(5) 0.0146(5) 0.0156(5) 0.0017(4) 0.0003(4) -0.0021(4) C6 0.0202(6) 0.0150(5) 0.0134(5) 0.0019(4) 0.0008(4) -0.0003(4) C7 0.0194(6) 0.0186(5) 0.0177(5) 0.0005(4) 0.0000(4) -0.0002(4) C8 0.0277(6) 0.0207(6) 0.0168(5) -0.0010(4) -0.0026(5) -0.0039(5) C9 0.0321(7) 0.0188(6) 0.0172(5) -0.0031(4) 0.0046(5) -0.0003(5) C10 0.0217(6) 0.0207(6) 0.0212(6) 0.0004(4) 0.0045(5) 0.0022(4) C11 0.0196(6) 0.0178(5) 0.0165(5) 0.0012(4) 0.0000(4) -0.0001(4) C12 0.0171(5) 0.0146(5) 0.0148(5) 0.0008(4) -0.0008(4) -0.0010(4) C13 0.0175(6) 0.0194(5) 0.0159(5) -0.0001(4) 0.0009(4) 0.0004(4) C14 0.0144(5) 0.0211(5) 0.0197(6) 0.0003(4) -0.0020(4) 0.0008(4) C15 0.0182(5) 0.0178(5) 0.0149(5) 0.0009(4) -0.0049(4) -0.0014(4) C16 0.0192(6) 0.0165(5) 0.0141(5) -0.0008(4) 0.0008(4) -0.0004(4) C17 0.0149(5) 0.0177(5) 0.0167(5) 0.0006(4) -0.0016(4) 0.0012(4) C18 0.0186(6) 0.0258(6) 0.0164(5) -0.0029(4) -0.0034(4) 0.0018(5) C19 0.0138(5) 0.0142(5) 0.0173(5) 0.0018(4) -0.0005(4) -0.0019(4) C20 0.0181(5) 0.0177(5) 0.0167(5) -0.0008(4) -0.0020(4) -0.0011(4) C21 0.0190(6) 0.0181(5) 0.0223(6) -0.0027(4) 0.0018(4) 0.0005(4) C22 0.0154(5) 0.0183(5) 0.0269(6) 0.0007(4) -0.0026(4) 0.0017(4) C23 0.0197(6) 0.0228(6) 0.0192(5) 0.0013(4) -0.0047(4) 0.0001(5) C24 0.0170(5) 0.0187(5) 0.0161(5) -0.0003(4) 0.0000(4) 0.0000(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 C16 1.3751(13) . ? O1 C18 1.4331(14) . ? O2 C15 1.3764(13) . ? O2 C18 1.4387(14) . ? N1 C1 1.3430(14) . ? N1 C5 1.3431(14) . ? C1 C2 1.3962(15) . ? C1 C6 1.4905(15) . ? C2 C3 1.3969(15) . ? C2 H2 0.9500 . ? C3 C4 1.3985(16) . ? C3 C12 1.4894(15) . ? C4 C5 1.3993(15) . ? C4 H4 0.9500 . ? C5 C19 1.4925(15) . ? C6 C11 1.3973(16) . ? C6 C7 1.3986(16) . ? C7 C8 1.3878(16) . ? C7 H7 0.9500 . ? C8 C9 1.3879(18) . ? C8 H8 0.9500 . ? C9 C10 1.3891(18) . ? C9 H9 0.9500 . ? C10 C11 1.3928(16) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.4007(16) . ? C12 C17 1.4137(15) . ? C13 C14 1.4027(15) . ? C13 H13 0.9500 . ? C14 C15 1.3727(16) . ? C14 H14 0.9500 . ? C15 C16 1.3826(16) . ? C16 C17 1.3740(15) . ? C17 H17 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.3968(16) . ? C19 C24 1.4000(15) . ? C20 C21 1.3903(16) . ? C20 H20 0.9500 . ? C21 C22 1.3906(16) . ? C21 H21 0.9500 . ? C22 C23 1.3896(17) . ? C22 H22 0.9500 . ? C23 C24 1.3868(16) . ? C23 H23 0.9500 . ? C24 H24 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 C16 O1 C18 105.78(9) . . ? C15 O2 C18 105.62(9) . . ? C1 N1 C5 118.42(9) . . ? N1 C1 C2 122.48(10) . . ? N1 C1 C6 116.05(10) . . ? C2 C1 C6 121.39(10) . . ? C1 C2 C3 119.87(10) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 117.00(10) . . ? C2 C3 C12 121.53(10) . . ? C4 C3 C12 121.46(10) . . ? C3 C4 C5 119.97(10) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 122.18(10) . . ? N1 C5 C19 115.67(9) . . ? C4 C5 C19 122.15(10) . . ? C11 C6 C7 118.58(10) . . ? C11 C6 C1 122.01(10) . . ? C7 C6 C1 119.38(10) . . ? C8 C7 C6 120.69(11) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.32(11) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C10 119.55(11) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C11 120.28(11) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C6 120.50(11) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C13 C12 C17 119.30(10) . . ? C13 C12 C3 120.75(10) . . ? C17 C12 C3 119.94(10) . . ? C12 C13 C14 122.28(10) . . ? C12 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? C15 C14 C13 116.75(10) . . ? C15 C14 H14 121.6 . . ? C13 C14 H14 121.6 . . ? C14 C15 O2 128.21(10) . . ? C14 C15 C16 121.75(10) . . ? O2 C15 C16 110.01(10) . . ? C17 C16 O1 127.46(10) . . ? C17 C16 C15 122.45(10) . . ? O1 C16 C15 110.07(10) . . ? C16 C17 C12 117.46(10) . . ? C16 C17 H17 121.3 . . ? C12 C17 H17 121.3 . . ? O1 C18 O2 108.15(9) . . ? O1 C18 H18A 110.1 . . ? O2 C18 H18A 110.1 . . ? O1 C18 H18B 110.1 . . ? O2 C18 H18B 110.1 . . ? H18A C18 H18B 108.4 . . ? C20 C19 C24 118.11(10) . . ? C20 C19 C5 122.13(10) . . ? C24 C19 C5 119.76(10) . . ? C21 C20 C19 121.01(10) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 120.21(11) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 119.33(11) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C24 C23 C22 120.42(11) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C19 120.91(11) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.5 . . ? _refine_diff_density_max 0.301 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.041 _shelx_res_file ; TITL i18213_a.res in P2(1)/n i18213.res created by SHELXL-2018/3 at 13:14:48 on 18-May-2021 REM Old TITL i18213 in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.102, Rweak 0.003, Alpha 0.023, Orientation as input REM Formula found by SHELXT: C24 N O2 CELL 0.71073 6.4058 12.1092 21.6453 90.000 92.249 90.000 ZERR 4.000 0.0002 0.0003 0.0007 0.000 0.001 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 96 68 4 8 ACTA TEMP -173.150 SIZE 0.09 0.284 0.362 L.S. 10 BOND $H LIST 6 FMAP 2 OMIT -1 2 2 OMIT 0 0 2 PLAN 5 WGHT 0.044600 0.729100 EXTI 0.016251 FVAR 1.01619 O1 4 0.912329 0.666355 0.516588 11.00000 0.02146 0.03372 = 0.01214 -0.00152 -0.00253 0.00660 O2 4 1.256665 0.605147 0.521734 11.00000 0.02015 0.03020 = 0.01440 -0.00214 -0.00407 0.00403 N1 3 0.612560 0.622194 0.174684 11.00000 0.01562 0.01608 = 0.01432 0.00061 0.00005 -0.00092 C1 1 0.788756 0.562649 0.181744 11.00000 0.01582 0.01423 = 0.01557 0.00083 0.00099 -0.00202 C2 1 0.903338 0.556792 0.237863 11.00000 0.01557 0.01563 = 0.01616 0.00155 0.00016 0.00044 AFIX 43 H2 2 1.024257 0.511480 0.241522 11.00000 -1.20000 AFIX 0 C3 1 0.839831 0.617690 0.288621 11.00000 0.01520 0.01555 = 0.01430 0.00156 -0.00056 -0.00267 C4 1 0.658351 0.681029 0.280266 11.00000 0.01695 0.01719 = 0.01408 -0.00070 0.00089 0.00005 AFIX 43 H4 2 0.610463 0.724818 0.313261 11.00000 -1.20000 AFIX 0 C5 1 0.547334 0.679879 0.223288 11.00000 0.01431 0.01456 = 0.01563 0.00172 0.00026 -0.00207 C6 1 0.850105 0.497721 0.126838 11.00000 0.02016 0.01500 = 0.01338 0.00188 0.00079 -0.00034 C7 1 0.697643 0.468618 0.081742 11.00000 0.01942 0.01863 = 0.01771 0.00047 0.00002 -0.00019 AFIX 43 H7 2 0.558244 0.493892 0.085324 11.00000 -1.20000 AFIX 0 C8 1 0.747858 0.403204 0.031816 11.00000 0.02767 0.02072 = 0.01680 -0.00098 -0.00264 -0.00385 AFIX 43 H8 2 0.643108 0.384663 0.001288 11.00000 -1.20000 AFIX 0 C9 1 0.950363 0.364741 0.026268 11.00000 0.03206 0.01881 = 0.01717 -0.00311 0.00458 -0.00028 AFIX 43 H9 2 0.983572 0.318186 -0.007281 11.00000 -1.20000 AFIX 0 C10 1 1.104157 0.394776 0.070101 11.00000 0.02175 0.02071 = 0.02119 0.00044 0.00453 0.00218 AFIX 43 H10 2 1.243316 0.369309 0.066254 11.00000 -1.20000 AFIX 0 C11 1 1.055189 0.462071 0.119664 11.00000 0.01959 0.01776 = 0.01652 0.00115 0.00003 -0.00008 AFIX 43 H11 2 1.162031 0.483899 0.148814 11.00000 -1.20000 AFIX 0 C12 1 0.957965 0.613875 0.349239 11.00000 0.01709 0.01455 = 0.01476 0.00076 -0.00076 -0.00097 C13 1 1.164673 0.576017 0.353266 11.00000 0.01751 0.01944 = 0.01586 -0.00006 0.00088 0.00041 AFIX 43 H13 2 1.229219 0.553644 0.316528 11.00000 -1.20000 AFIX 0 C14 1 1.279675 0.569993 0.409662 11.00000 0.01440 0.02107 = 0.01972 0.00034 -0.00196 0.00082 AFIX 43 H14 2 1.419315 0.543442 0.411955 11.00000 -1.20000 AFIX 0 C15 1 1.180614 0.604332 0.461375 11.00000 0.01816 0.01776 = 0.01489 0.00086 -0.00494 -0.00140 C16 1 0.976355 0.641439 0.458314 11.00000 0.01920 0.01650 = 0.01410 -0.00077 0.00077 -0.00037 C17 1 0.860561 0.647491 0.403628 11.00000 0.01487 0.01771 = 0.01667 0.00056 -0.00163 0.00118 AFIX 43 H17 2 0.720398 0.673280 0.402412 11.00000 -1.20000 AFIX 0 C18 1 1.092301 0.651178 0.557137 11.00000 0.01856 0.02578 = 0.01641 -0.00287 -0.00344 0.00178 AFIX 23 H18A 2 1.058679 0.600607 0.591281 11.00000 -1.20000 H18B 2 1.137109 0.722872 0.575198 11.00000 -1.20000 AFIX 0 C19 1 0.349208 0.743075 0.212527 11.00000 0.01378 0.01425 = 0.01726 0.00180 -0.00053 -0.00191 C20 1 0.252870 0.799156 0.260076 11.00000 0.01814 0.01765 = 0.01670 -0.00081 -0.00199 -0.00113 AFIX 43 H20 2 0.314444 0.797461 0.300713 11.00000 -1.20000 AFIX 0 C21 1 0.068252 0.857417 0.248840 11.00000 0.01899 0.01813 = 0.02229 -0.00273 0.00183 0.00049 AFIX 43 H21 2 0.004827 0.895077 0.281728 11.00000 -1.20000 AFIX 0 C22 1 -0.023866 0.860742 0.189618 11.00000 0.01538 0.01827 = 0.02690 0.00074 -0.00255 0.00174 AFIX 43 H22 2 -0.149740 0.900734 0.181821 11.00000 -1.20000 AFIX 0 C23 1 0.070068 0.804973 0.141958 11.00000 0.01974 0.02285 = 0.01924 0.00126 -0.00466 0.00005 AFIX 43 H23 2 0.008299 0.807114 0.101350 11.00000 -1.20000 AFIX 0 C24 1 0.253412 0.746211 0.153297 11.00000 0.01699 0.01872 = 0.01613 -0.00027 0.00000 -0.00004 AFIX 43 H24 2 0.314848 0.707552 0.120418 11.00000 -1.20000 AFIX 0 HKLF 4 REM i18213_a.res in P2(1)/n REM wR2 = 0.095567, GooF = S = 1.02935, Restrained GooF = 1.02935 for all data REM R1 = 0.035416 for 3271 Fo > 4sig(Fo) and 0.041227 for all 3704 data REM 245 parameters refined using 0 restraints END WGHT 0.0446 0.7289 REM Highest difference peak 0.301, deepest hole -0.182, 1-sigma level 0.041 Q1 1 0.9050 0.6217 0.3179 11.00000 0.05 0.30 Q2 1 0.4498 0.7132 0.2185 11.00000 0.05 0.30 Q3 1 0.5973 0.6824 0.2514 11.00000 0.05 0.26 Q4 1 0.8191 0.5284 0.1520 11.00000 0.05 0.26 Q5 1 1.0774 0.6282 0.4549 11.00000 0.05 0.26 ; _shelx_res_checksum 53097 ####################################################################### # # 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_i18212 _database_code_depnum_ccdc_archive 'CCDC 2085361' loop_ _audit_author_name _audit_author_address 'Chieh-Kai Chan' 'Academia Sinica' _audit_update_record ; 2021-05-24 deposited with the CCDC. 2022-03-01 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 'C30 H26 N2' _chemical_formula_sum 'C30 H26 N2' _chemical_formula_weight 414.53 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 triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _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' _cell_length_a 9.8179(3) _cell_length_b 10.4973(3) _cell_length_c 11.9206(3) _cell_angle_alpha 76.3210(10) _cell_angle_beta 87.7270(10) _cell_angle_gamma 66.7560(10) _cell_volume 1094.83(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 9940 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 30.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.257 _exptl_crystal_F_000 440 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.369 _exptl_crystal_size_mid 0.277 _exptl_crystal_size_min 0.214 _exptl_absorpt_coefficient_mu 0.073 _shelx_estimated_absorpt_T_min 0.974 _shelx_estimated_absorpt_T_max 0.985 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9701 _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 54798 _diffrn_reflns_av_unetI/netI 0.0244 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.761 _diffrn_reflns_theta_max 30.034 _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 0.997 _diffrn_reflns_point_group_measured_fraction_full 0.996 _reflns_number_total 6393 _reflns_number_gt 5364 _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^)+(0.0539P)^2^+0.3917P] 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 6393 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.70705(9) 0.44975(9) 0.47178(7) 0.01501(16) Uani 1 1 d . . . . . H1 H 0.6434(16) 0.4235(15) 0.5205(12) 0.024(3) Uiso 1 1 d . . . . . N2 N 0.52102(9) 0.67358(9) 0.35981(7) 0.01470(16) Uani 1 1 d . . . . . C1 C 0.65583(11) 0.60651(10) 0.44030(8) 0.01419(18) Uani 1 1 d . . . . . C2 C 0.69909(10) 0.51498(10) 0.26011(8) 0.01350(17) Uani 1 1 d . . . . . H2 H 0.706660 0.481443 0.187365 0.016 Uiso 1 1 calc R U . . . C3 C 0.72142(10) 0.39111(10) 0.36900(8) 0.01368(17) Uani 1 1 d . . . . . H3 H 0.638923 0.358460 0.366553 0.016 Uiso 1 1 calc R U . . . C4 C 0.54595(10) 0.62552(10) 0.26757(8) 0.01363(17) Uani 1 1 d . . . . . C5 C 0.81121(11) 0.58452(10) 0.26631(8) 0.01410(18) Uani 1 1 d . . . . . H5 H 0.913911 0.508361 0.274519 0.017 Uiso 1 1 calc R U . . . C6 C 0.78276(11) 0.64032(11) 0.37764(8) 0.01622(18) Uani 1 1 d . . . . . H6A H 0.874268 0.594221 0.429275 0.019 Uiso 1 1 calc R U . . . H6AB H 0.755435 0.744756 0.357640 0.019 Uiso 1 1 calc R U . . . C7 C 0.86703(11) 0.26422(10) 0.37154(8) 0.01450(18) Uani 1 1 d . . . . . C8 C 0.99689(12) 0.24778(11) 0.42732(9) 0.0198(2) Uani 1 1 d . . . . . H8 H 0.995269 0.316749 0.467137 0.024 Uiso 1 1 calc R U . . . C9 C 1.12921(12) 0.13129(12) 0.42542(10) 0.0223(2) Uani 1 1 d . . . . . H9 H 1.217433 0.122104 0.462802 0.027 Uiso 1 1 calc R U . . . C10 C 1.13259(12) 0.02868(12) 0.36912(9) 0.0220(2) Uani 1 1 d . . . . . H10 H 1.222675 -0.051111 0.368259 0.026 Uiso 1 1 calc R U . . . C11 C 1.00339(13) 0.04339(12) 0.31402(10) 0.0231(2) Uani 1 1 d . . . . . H11 H 1.004823 -0.026848 0.275735 0.028 Uiso 1 1 calc R U . . . C12 C 0.87193(12) 0.16074(11) 0.31478(9) 0.0185(2) Uani 1 1 d . . . . . H12 H 0.784284 0.170550 0.276115 0.022 Uiso 1 1 calc R U . . . C13 C 0.42685(11) 0.67372(10) 0.17532(8) 0.01451(18) Uani 1 1 d . . . . . C14 C 0.46172(11) 0.65558(11) 0.06374(9) 0.01725(19) Uani 1 1 d . . . . . H14 H 0.562702 0.613619 0.046281 0.021 Uiso 1 1 calc R U . . . C15 C 0.34962(12) 0.69853(11) -0.02200(9) 0.0201(2) Uani 1 1 d . . . . . H15 H 0.374490 0.685936 -0.097589 0.024 Uiso 1 1 calc R U . . . C16 C 0.20178(12) 0.75963(12) 0.00253(9) 0.0220(2) Uani 1 1 d . . . . . H16 H 0.125455 0.788455 -0.055991 0.026 Uiso 1 1 calc R U . . . C17 C 0.16560(12) 0.77859(12) 0.11348(10) 0.0217(2) Uani 1 1 d . . . . . H17 H 0.064428 0.820279 0.130539 0.026 Uiso 1 1 calc R U . . . C18 C 0.27709(11) 0.73668(11) 0.19904(9) 0.01755(19) Uani 1 1 d . . . . . H18 H 0.251738 0.750755 0.274203 0.021 Uiso 1 1 calc R U . . . C19 C 0.79635(11) 0.69585(10) 0.15452(8) 0.01520(18) Uani 1 1 d . . . . . C20 C 0.70232(12) 0.83966(11) 0.13775(9) 0.0214(2) Uani 1 1 d . . . . . H20 H 0.647155 0.872979 0.199735 0.026 Uiso 1 1 calc R U . . . C21 C 0.68834(14) 0.93509(12) 0.03112(10) 0.0263(2) Uani 1 1 d . . . . . H21 H 0.624979 1.033060 0.021446 0.032 Uiso 1 1 calc R U . . . C22 C 0.76590(13) 0.88842(12) -0.06076(10) 0.0248(2) Uani 1 1 d . . . . . H22 H 0.755463 0.953735 -0.133476 0.030 Uiso 1 1 calc R U . . . C23 C 0.85902(13) 0.74550(12) -0.04586(9) 0.0232(2) Uani 1 1 d . . . . . H23 H 0.912208 0.712415 -0.108656 0.028 Uiso 1 1 calc R U . . . C24 C 0.87458(12) 0.65051(11) 0.06110(9) 0.0196(2) Uani 1 1 d . . . . . H24 H 0.939624 0.553030 0.070746 0.023 Uiso 1 1 calc R U . . . C25 C 0.62522(11) 0.66473(11) 0.54795(8) 0.01539(18) Uani 1 1 d . . . . . C26 C 0.70918(12) 0.58479(11) 0.65147(9) 0.0199(2) Uani 1 1 d . . . . . H26 H 0.783573 0.492168 0.655167 0.024 Uiso 1 1 calc R U . . . C27 C 0.68460(13) 0.63984(13) 0.74919(9) 0.0238(2) Uani 1 1 d . . . . . H27 H 0.740618 0.583762 0.819700 0.029 Uiso 1 1 calc R U . . . C28 C 0.57846(13) 0.77656(13) 0.74416(9) 0.0232(2) Uani 1 1 d . . . . . H28 H 0.562363 0.814352 0.810777 0.028 Uiso 1 1 calc R U . . . C29 C 0.49611(12) 0.85750(12) 0.64105(9) 0.0208(2) Uani 1 1 d . . . . . H29 H 0.423999 0.951251 0.637030 0.025 Uiso 1 1 calc R U . . . C30 C 0.51877(11) 0.80183(11) 0.54336(9) 0.01795(19) Uani 1 1 d . . . . . H30 H 0.461409 0.857563 0.473335 0.022 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 0.0168(4) 0.0147(4) 0.0135(4) -0.0032(3) 0.0016(3) -0.0064(3) N2 0.0145(4) 0.0148(4) 0.0146(4) -0.0033(3) 0.0001(3) -0.0058(3) C1 0.0141(4) 0.0149(4) 0.0140(4) -0.0040(3) 0.0005(3) -0.0058(3) C2 0.0130(4) 0.0134(4) 0.0134(4) -0.0030(3) 0.0003(3) -0.0046(3) C3 0.0128(4) 0.0133(4) 0.0147(4) -0.0029(3) 0.0000(3) -0.0051(3) C4 0.0137(4) 0.0120(4) 0.0149(4) -0.0020(3) 0.0004(3) -0.0054(3) C5 0.0133(4) 0.0150(4) 0.0140(4) -0.0034(3) 0.0015(3) -0.0057(3) C6 0.0172(4) 0.0195(5) 0.0150(4) -0.0054(3) 0.0020(3) -0.0097(4) C7 0.0146(4) 0.0135(4) 0.0141(4) -0.0011(3) 0.0011(3) -0.0054(3) C8 0.0174(5) 0.0171(5) 0.0247(5) -0.0058(4) -0.0023(4) -0.0060(4) C9 0.0158(5) 0.0219(5) 0.0264(5) -0.0037(4) -0.0039(4) -0.0053(4) C10 0.0177(5) 0.0191(5) 0.0225(5) -0.0037(4) 0.0004(4) -0.0010(4) C11 0.0227(5) 0.0199(5) 0.0249(5) -0.0095(4) -0.0004(4) -0.0040(4) C12 0.0172(5) 0.0183(5) 0.0192(5) -0.0055(4) -0.0009(4) -0.0053(4) C13 0.0153(4) 0.0116(4) 0.0161(4) -0.0028(3) -0.0011(3) -0.0049(3) C14 0.0165(4) 0.0171(4) 0.0174(4) -0.0048(4) 0.0003(3) -0.0055(4) C15 0.0217(5) 0.0218(5) 0.0164(4) -0.0050(4) -0.0015(4) -0.0079(4) C16 0.0188(5) 0.0250(5) 0.0213(5) -0.0047(4) -0.0049(4) -0.0075(4) C17 0.0152(5) 0.0235(5) 0.0244(5) -0.0070(4) -0.0007(4) -0.0049(4) C18 0.0173(5) 0.0168(4) 0.0183(4) -0.0057(4) 0.0007(4) -0.0058(4) C19 0.0149(4) 0.0165(4) 0.0157(4) -0.0038(3) 0.0016(3) -0.0079(4) C20 0.0242(5) 0.0167(5) 0.0219(5) -0.0050(4) 0.0040(4) -0.0067(4) C21 0.0312(6) 0.0160(5) 0.0279(6) -0.0005(4) -0.0001(5) -0.0082(4) C22 0.0311(6) 0.0252(5) 0.0195(5) 0.0021(4) -0.0017(4) -0.0165(5) C23 0.0286(6) 0.0278(5) 0.0168(5) -0.0057(4) 0.0043(4) -0.0151(5) C24 0.0214(5) 0.0190(5) 0.0178(5) -0.0049(4) 0.0037(4) -0.0074(4) C25 0.0168(4) 0.0187(4) 0.0143(4) -0.0058(3) 0.0032(3) -0.0100(4) C26 0.0237(5) 0.0206(5) 0.0164(4) -0.0041(4) 0.0006(4) -0.0098(4) C27 0.0321(6) 0.0279(5) 0.0146(4) -0.0051(4) 0.0002(4) -0.0153(5) C28 0.0291(6) 0.0300(6) 0.0191(5) -0.0123(4) 0.0076(4) -0.0175(5) C29 0.0206(5) 0.0229(5) 0.0239(5) -0.0116(4) 0.0062(4) -0.0109(4) C30 0.0176(5) 0.0203(5) 0.0183(5) -0.0067(4) 0.0023(4) -0.0089(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 N1 C1 1.4735(12) . ? N1 C3 1.4746(12) . ? N1 H1 0.913(15) . ? N2 C4 1.2912(12) . ? N2 C1 1.4879(12) . ? C1 C25 1.5185(13) . ? C1 C6 1.5449(13) . ? C2 C4 1.5087(13) . ? C2 C5 1.5545(13) . ? C2 C3 1.5567(13) . ? C2 H2 1.0000 . ? C3 C7 1.5167(13) . ? C3 H3 1.0000 . ? C4 C13 1.4847(13) . ? C5 C19 1.5189(13) . ? C5 C6 1.5463(13) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6AB 0.9900 . ? C7 C8 1.3916(14) . ? C7 C12 1.3942(14) . ? C8 C9 1.3930(14) . ? C8 H8 0.9500 . ? C9 C10 1.3870(16) . ? C9 H9 0.9500 . ? C10 C11 1.3884(16) . ? C10 H10 0.9500 . ? C11 C12 1.3903(14) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.3982(13) . ? C13 C18 1.4024(14) . ? C14 C15 1.3924(14) . ? C14 H14 0.9500 . ? C15 C16 1.3870(15) . ? C15 H15 0.9500 . ? C16 C17 1.3951(15) . ? C16 H16 0.9500 . ? C17 C18 1.3886(14) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.3939(14) . ? C19 C24 1.3968(13) . ? C20 C21 1.3932(15) . ? C20 H20 0.9500 . ? C21 C22 1.3831(17) . ? C21 H21 0.9500 . ? C22 C23 1.3865(16) . ? C22 H22 0.9500 . ? C23 C24 1.3918(15) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.3952(14) . ? C25 C26 1.3970(14) . ? C26 C27 1.3912(14) . ? C26 H26 0.9500 . ? C27 C28 1.3904(16) . ? C27 H27 0.9500 . ? C28 C29 1.3889(16) . ? C28 H28 0.9500 . ? C29 C30 1.3949(14) . ? C29 H29 0.9500 . ? C30 H30 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 C3 111.90(7) . . ? C1 N1 H1 110.0(9) . . ? C3 N1 H1 110.2(9) . . ? C4 N2 C1 110.96(8) . . ? N1 C1 N2 111.06(8) . . ? N1 C1 C25 110.48(8) . . ? N2 C1 C25 110.38(8) . . ? N1 C1 C6 106.61(8) . . ? N2 C1 C6 108.65(8) . . ? C25 C1 C6 109.57(8) . . ? C4 C2 C5 107.25(8) . . ? C4 C2 C3 104.77(7) . . ? C5 C2 C3 110.69(8) . . ? C4 C2 H2 111.3 . . ? C5 C2 H2 111.3 . . ? C3 C2 H2 111.3 . . ? N1 C3 C7 113.04(8) . . ? N1 C3 C2 107.76(7) . . ? C7 C3 C2 112.19(8) . . ? N1 C3 H3 107.9 . . ? C7 C3 H3 107.9 . . ? C2 C3 H3 107.9 . . ? N2 C4 C13 121.07(8) . . ? N2 C4 C2 117.04(8) . . ? C13 C4 C2 121.85(8) . . ? C19 C5 C6 115.65(8) . . ? C19 C5 C2 109.58(8) . . ? C6 C5 C2 106.65(7) . . ? C19 C5 H5 108.2 . . ? C6 C5 H5 108.2 . . ? C2 C5 H5 108.2 . . ? C1 C6 C5 109.59(8) . . ? C1 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? C1 C6 H6AB 109.8 . . ? C5 C6 H6AB 109.8 . . ? H6A C6 H6AB 108.2 . . ? C8 C7 C12 118.55(9) . . ? C8 C7 C3 122.48(9) . . ? C12 C7 C3 118.96(9) . . ? C7 C8 C9 120.72(10) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 120.22(10) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.54(10) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.11(10) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 120.86(10) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? C14 C13 C18 118.80(9) . . ? C14 C13 C4 120.68(9) . . ? C18 C13 C4 120.51(9) . . ? C15 C14 C13 120.52(9) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 120.26(10) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 119.75(10) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 120.17(10) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C13 120.49(9) . . ? C17 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? C20 C19 C24 118.01(9) . . ? C20 C19 C5 123.60(9) . . ? C24 C19 C5 118.29(9) . . ? C21 C20 C19 120.74(10) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C22 C21 C20 120.56(10) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 119.45(10) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C22 C23 C24 120.00(10) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C19 121.22(10) . . ? C23 C24 H24 119.4 . . ? C19 C24 H24 119.4 . . ? C30 C25 C26 118.98(9) . . ? C30 C25 C1 120.55(9) . . ? C26 C25 C1 120.36(9) . . ? C27 C26 C25 120.47(10) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C28 C27 C26 120.31(10) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C29 C28 C27 119.53(10) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C28 C29 C30 120.33(10) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C29 C30 C25 120.35(10) . . ? C29 C30 H30 119.8 . . ? C25 C30 H30 119.8 . . ? _refine_diff_density_max 0.392 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.045 _shelx_res_file ; TITL i18212_a.res in P-1 i18212.res created by SHELXL-2018/3 at 15:04:17 on 18-May-2021 REM Old TITL i18212 in P-1 REM SHELXT solution in P-1 REM R1 0.119, Rweak 0.005, Alpha 0.034, Orientation as input REM Formula found by SHELXT: C30 O2 CELL 0.71073 9.8179 10.4973 11.9206 76.321 87.727 66.756 ZERR 2.000 0.0003 0.0003 0.0003 0.001 0.001 0.001 LATT 1 SFAC C H N UNIT 60 52 4 ACTA TEMP -173.150 SIZE 0.214 0.277 0.369 L.S. 10 BOND $H OMIT 0 1 2 OMIT 0 1 0 OMIT -1 -2 2 LIST 6 FMAP 2 PLAN 3 WGHT 0.053900 0.391700 FVAR 1.34631 N1 3 0.707045 0.449755 0.471775 11.00000 0.01681 0.01469 = 0.01350 -0.00320 0.00162 -0.00639 H1 2 0.643416 0.423533 0.520454 11.00000 0.02439 N2 3 0.521024 0.673585 0.359809 11.00000 0.01454 0.01483 = 0.01463 -0.00330 0.00009 -0.00580 C1 1 0.655827 0.606514 0.440301 11.00000 0.01407 0.01487 = 0.01395 -0.00397 0.00053 -0.00578 C2 1 0.699092 0.514983 0.260106 11.00000 0.01305 0.01340 = 0.01337 -0.00302 0.00031 -0.00460 AFIX 13 H2 2 0.706660 0.481443 0.187365 11.00000 -1.20000 AFIX 0 C3 1 0.721419 0.391107 0.369000 11.00000 0.01277 0.01333 = 0.01472 -0.00292 -0.00003 -0.00512 AFIX 13 H3 2 0.638923 0.358460 0.366553 11.00000 -1.20000 AFIX 0 C4 1 0.545948 0.625518 0.267565 11.00000 0.01367 0.01201 = 0.01488 -0.00203 0.00037 -0.00541 C5 1 0.811211 0.584524 0.266312 11.00000 0.01331 0.01502 = 0.01395 -0.00339 0.00148 -0.00572 AFIX 13 H5 2 0.913911 0.508361 0.274519 11.00000 -1.20000 AFIX 0 C6 1 0.782758 0.640315 0.377637 11.00000 0.01716 0.01953 = 0.01496 -0.00543 0.00199 -0.00975 AFIX 23 H6A 2 0.874268 0.594221 0.429275 11.00000 -1.20000 H6AB 2 0.755435 0.744756 0.357640 11.00000 -1.20000 AFIX 0 C7 1 0.867032 0.264216 0.371540 11.00000 0.01456 0.01347 = 0.01406 -0.00109 0.00106 -0.00537 C8 1 0.996885 0.247780 0.427324 11.00000 0.01740 0.01714 = 0.02467 -0.00584 -0.00232 -0.00600 AFIX 43 H8 2 0.995269 0.316749 0.467137 11.00000 -1.20000 AFIX 0 C9 1 1.129210 0.131292 0.425416 11.00000 0.01575 0.02185 = 0.02637 -0.00369 -0.00391 -0.00525 AFIX 43 H9 2 1.217433 0.122104 0.462802 11.00000 -1.20000 AFIX 0 C10 1 1.132590 0.028679 0.369116 11.00000 0.01767 0.01909 = 0.02246 -0.00370 0.00041 -0.00102 AFIX 43 H10 2 1.222675 -0.051111 0.368259 11.00000 -1.20000 AFIX 0 C11 1 1.003391 0.043389 0.314017 11.00000 0.02266 0.01986 = 0.02490 -0.00955 -0.00039 -0.00403 AFIX 43 H11 2 1.004823 -0.026848 0.275735 11.00000 -1.20000 AFIX 0 C12 1 0.871927 0.160741 0.314778 11.00000 0.01717 0.01827 = 0.01917 -0.00546 -0.00089 -0.00533 AFIX 43 H12 2 0.784284 0.170550 0.276115 11.00000 -1.20000 AFIX 0 C13 1 0.426846 0.673719 0.175323 11.00000 0.01529 0.01162 = 0.01610 -0.00283 -0.00106 -0.00491 C14 1 0.461723 0.655579 0.063738 11.00000 0.01645 0.01713 = 0.01745 -0.00484 0.00028 -0.00546 AFIX 43 H14 2 0.562702 0.613619 0.046281 11.00000 -1.20000 AFIX 0 C15 1 0.349621 0.698529 -0.021996 11.00000 0.02172 0.02183 = 0.01635 -0.00500 -0.00147 -0.00786 AFIX 43 H15 2 0.374490 0.685936 -0.097589 11.00000 -1.20000 AFIX 0 C16 1 0.201783 0.759628 0.002534 11.00000 0.01878 0.02499 = 0.02127 -0.00473 -0.00493 -0.00750 AFIX 43 H16 2 0.125455 0.788455 -0.055991 11.00000 -1.20000 AFIX 0 C17 1 0.165602 0.778588 0.113482 11.00000 0.01520 0.02353 = 0.02445 -0.00696 -0.00069 -0.00495 AFIX 43 H17 2 0.064428 0.820279 0.130539 11.00000 -1.20000 AFIX 0 C18 1 0.277093 0.736677 0.199040 11.00000 0.01731 0.01685 = 0.01834 -0.00570 0.00069 -0.00576 AFIX 43 H18 2 0.251738 0.750755 0.274203 11.00000 -1.20000 AFIX 0 C19 1 0.796345 0.695851 0.154521 11.00000 0.01494 0.01653 = 0.01565 -0.00384 0.00156 -0.00789 C20 1 0.702321 0.839663 0.137755 11.00000 0.02415 0.01671 = 0.02190 -0.00502 0.00401 -0.00669 AFIX 43 H20 2 0.647155 0.872979 0.199735 11.00000 -1.20000 AFIX 0 C21 1 0.688336 0.935092 0.031124 11.00000 0.03119 0.01602 = 0.02795 -0.00051 -0.00006 -0.00817 AFIX 43 H21 2 0.624979 1.033060 0.021446 11.00000 -1.20000 AFIX 0 C22 1 0.765902 0.888417 -0.060759 11.00000 0.03111 0.02522 = 0.01951 0.00206 -0.00166 -0.01652 AFIX 43 H22 2 0.755463 0.953735 -0.133476 11.00000 -1.20000 AFIX 0 C23 1 0.859023 0.745503 -0.045858 11.00000 0.02856 0.02781 = 0.01680 -0.00565 0.00430 -0.01506 AFIX 43 H23 2 0.912208 0.712415 -0.108656 11.00000 -1.20000 AFIX 0 C24 1 0.874585 0.650510 0.061101 11.00000 0.02139 0.01896 = 0.01780 -0.00489 0.00366 -0.00743 AFIX 43 H24 2 0.939624 0.553030 0.070746 11.00000 -1.20000 AFIX 0 C25 1 0.625218 0.664730 0.547947 11.00000 0.01677 0.01874 = 0.01432 -0.00584 0.00316 -0.00998 C26 1 0.709175 0.584786 0.651472 11.00000 0.02366 0.02055 = 0.01638 -0.00409 0.00062 -0.00976 AFIX 43 H26 2 0.783573 0.492168 0.655167 11.00000 -1.20000 AFIX 0 C27 1 0.684604 0.639845 0.749194 11.00000 0.03210 0.02792 = 0.01464 -0.00515 0.00021 -0.01528 AFIX 43 H27 2 0.740618 0.583762 0.819700 11.00000 -1.20000 AFIX 0 C28 1 0.578455 0.776565 0.744160 11.00000 0.02911 0.02997 = 0.01907 -0.01229 0.00758 -0.01755 AFIX 43 H28 2 0.562363 0.814352 0.810777 11.00000 -1.20000 AFIX 0 C29 1 0.496114 0.857501 0.641049 11.00000 0.02063 0.02288 = 0.02391 -0.01156 0.00617 -0.01094 AFIX 43 H29 2 0.423999 0.951251 0.637030 11.00000 -1.20000 AFIX 0 C30 1 0.518768 0.801829 0.543362 11.00000 0.01759 0.02028 = 0.01829 -0.00668 0.00229 -0.00888 AFIX 43 H30 2 0.461409 0.857563 0.473335 11.00000 -1.20000 REM ##### REM ##### REM ##### AFIX 0 HKLF 4 REM i18212_a.res in P-1 REM wR2 = 0.113120, GooF = S = 1.03226, Restrained GooF = 1.03226 for all data REM R1 = 0.042257 for 5364 Fo > 4sig(Fo) and 0.052854 for all 6393 data REM 293 parameters refined using 0 restraints END WGHT 0.0538 0.3920 REM Highest difference peak 0.392, deepest hole -0.233, 1-sigma level 0.045 Q1 1 0.6239 0.5671 0.2628 11.00000 0.05 0.39 Q2 1 0.4847 0.6527 0.2202 11.00000 0.05 0.36 Q3 1 0.6310 0.6379 0.4954 11.00000 0.05 0.35 ; _shelx_res_checksum 21768