#============================================================================= data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 13 _journal_issue 2 _journal_year 2022 _journal_page_first 135 _journal_page_last 144 #============================================================================= data_mo_d5_0m_a _audit_creation_date 2022-01-30 _audit_creation_method ; Olex2 1.3-beta (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_contact_author_address ? _audit_contact_author_email ? _audit_contact_author_name '' _audit_contact_author_phone ? _publ_contact_author_id_orcid ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H21 N4 O2' _chemical_formula_sum 'C21 H21 N4 O2' _chemical_formula_weight 361.42 _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' _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 14.641(13) _cell_length_b 8.653(4) _cell_length_c 16.609(10) _cell_angle_alpha 90.00 _cell_angle_beta 116.34(3) _cell_angle_gamma 90.00 _cell_volume 1886(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 29176 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 31.77 _cell_measurement_theta_min 2.66 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.3487 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ? _exptl_crystal_colour grey _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 764 _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1593 _diffrn_reflns_av_unetI/netI 0.0721 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 31296 _diffrn_reflns_theta_full 23.99 _diffrn_reflns_theta_max 23.99 _diffrn_reflns_theta_min 2.82 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_device_type 'Bruker D8 Venture area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1973 _reflns_number_total 2888 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution ? _refine_diff_density_max 0.338 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.072 _refine_ls_extinction_coef 0.029(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 255 _refine_ls_number_reflns 2888 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1297 _refine_ls_R_factor_gt 0.0963 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1489P)^2^+1.0545P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2494 _refine_ls_wR_factor_ref 0.2697 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Others Fixed Uiso: H9(0.064) H2(0.065) H10(0.068) H4(0.086) H14A(0.077) H5(0.092) H11A(0.089) H11B(0.089) H12A(0.096) H12B(0.096) H13A(0.096) H13B(0.096) H7A(0.159) H7B(0.159) H7C(0.159) H8A(0.124) H8B(0.124) H8C(0.124) Fixed X: H9(0.3393) H2(0.2562) H10(0.4143) H4(0.0318) H14A(0.6393) H5(0.0706) H11A(0.4596) H11B(0.4276) H12A(0.5871) H12B(0.6016) H13A(0.712) H13B(0.6491) H7A(0.1622) H7B(0.189) H7C(0.0903) H8A(-0.02) H8B(0.0272) H8C(0.0087) Fixed Y: H9(0.996) H2(0.722) H10(0.8641) H4(0.5467) H14A(1.1012) H5(0.7223) H11A(0.7782) H11B(0.6686) H12A(0.7112) H12B(0.6376) H13A(0.8549) H13B(0.8695) H7A(0.8462) H7B(1.0224) H7C(0.9697) H8A(0.5308) H8B(0.3823) H8C(0.3887) Fixed Z: H9(0.2214) H2(0.3362) H10(0.3949) H4(0.1122) H14A(0.4064) H5(0.028) H11A(0.2534) H11B(0.3117) H12A(0.4367) H12B(0.3566) H13A(0.425) H13B(0.3203) H7A(-0.0355) H7B(-0.0314) H7C(-0.0244) H8A(0.2501) H8B(0.3077) H8C(0.2073) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1270(2) 0.5095(3) 0.28894(19) 0.0654(9) Uani 1 1 d . . . C15 C 0.5017(3) 1.0293(5) 0.3751(2) 0.0528(10) Uani 1 1 d . . . O2 O 0.2162(3) 0.9339(4) 0.08594(18) 0.0821(11) Uani 1 1 d . . . C16 C 0.4612(3) 1.1784(5) 0.3887(2) 0.0524(10) Uani 1 1 d . . . C9 C 0.3240(3) 0.9538(5) 0.2689(2) 0.0535(10) Uani 1 1 d . . . H9 H 0.3393 0.9960 0.2214 0.064 Uiso 1 1 calc R . . C2 C 0.2190(3) 0.7225(5) 0.2739(2) 0.0540(10) Uani 1 1 d . . . H2 H 0.2562 0.7220 0.3362 0.065 Uiso 1 1 calc R . . C18 C 0.2798(3) 1.0909(5) 0.3025(2) 0.0540(10) Uani 1 1 d . . . C19 C 0.5330(3) 1.2929(5) 0.4426(3) 0.0576(10) Uani 1 1 d . . . C17 C 0.3606(3) 1.2125(5) 0.3557(2) 0.0523(10) Uani 1 1 d . . . C3 C 0.1409(3) 0.6150(5) 0.2333(3) 0.0577(11) Uani 1 1 d . . . C1 C 0.2426(3) 0.8298(5) 0.2245(2) 0.0548(10) Uani 1 1 d . . . C10 C 0.4263(3) 0.8970(5) 0.3439(3) 0.0564(10) Uani 1 1 d . . . H10 H 0.4143 0.8641 0.3949 0.068 Uiso 1 1 calc R . . N1 N 0.3227(3) 1.3475(5) 0.3703(3) 0.0694(11) Uani 1 1 d . . . C21 C 0.1948(3) 1.1628(5) 0.2231(3) 0.0612(11) Uani 1 1 d . . . N3 N 0.2049(3) 0.9942(6) 0.4110(3) 0.0825(13) Uani 1 1 d . . . C20 C 0.2368(3) 1.0358(5) 0.3635(3) 0.0595(11) Uani 1 1 d . . . C4 C 0.0848(4) 0.6166(6) 0.1404(3) 0.0717(13) Uani 1 1 d . . . H4 H 0.0318 0.5467 0.1122 0.086 Uiso 1 1 calc R . . C6 C 0.1858(3) 0.8272(5) 0.1305(3) 0.0641(12) Uani 1 1 d . . . N4 N 0.1295(3) 1.2141(5) 0.1620(3) 0.0814(12) Uani 1 1 d . . . N2 N 0.5879(3) 1.3853(5) 0.4886(3) 0.0762(12) Uani 1 1 d . . . C14 C 0.5979(3) 1.0142(5) 0.3884(3) 0.0645(12) Uani 1 1 d . . . H14A H 0.6393 1.1012 0.4064 0.077 Uiso 1 1 calc R . . C5 C 0.1081(4) 0.7221(6) 0.0902(3) 0.0765(14) Uani 1 1 d . . . H5 H 0.0706 0.7223 0.0280 0.092 Uiso 1 1 calc R . . C11 C 0.4672(4) 0.7595(6) 0.3137(3) 0.0738(13) Uani 1 1 d . . . H11A H 0.4596 0.7782 0.2534 0.089 Uiso 1 1 calc R . . H11B H 0.4276 0.6686 0.3117 0.089 Uiso 1 1 calc R . . C12 C 0.5790(4) 0.7294(6) 0.3762(3) 0.0799(14) Uani 1 1 d . . . H12A H 0.5871 0.7112 0.4367 0.096 Uiso 1 1 calc R . . H12B H 0.6016 0.6376 0.3566 0.096 Uiso 1 1 calc R . . C13 C 0.6439(4) 0.8663(7) 0.3765(3) 0.0802(15) Uani 1 1 d . . . H13A H 0.7120 0.8549 0.4250 0.096 Uiso 1 1 calc R . . H13B H 0.6491 0.8695 0.3203 0.096 Uiso 1 1 calc R . . C7 C 0.1599(5) 0.9439(9) -0.0091(3) 0.106(2) Uani 1 1 d . . . H7A H 0.1622 0.8462 -0.0355 0.159 Uiso 1 1 calc R . . H7B H 0.1890 1.0224 -0.0314 0.159 Uiso 1 1 calc R . . H7C H 0.0903 0.9697 -0.0244 0.159 Uiso 1 1 calc R . . C8 C 0.0276(3) 0.4478(7) 0.2613(4) 0.0825(15) Uani 1 1 d . . . H8A H -0.0200 0.5308 0.2501 0.124 Uiso 1 1 calc R . . H8B H 0.0272 0.3823 0.3077 0.124 Uiso 1 1 calc R . . H8C H 0.0087 0.3887 0.2073 0.124 Uiso 1 1 calc R . . H11 H 0.254(4) 1.374(5) 0.337(3) 0.067(13) Uiso 1 1 d . . . H12 H 0.366(4) 1.414(6) 0.412(3) 0.083(15) 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 O1 0.0700(17) 0.0607(19) 0.0595(17) 0.0044(13) 0.0233(14) -0.0059(13) C15 0.067(2) 0.055(3) 0.0351(18) 0.0018(15) 0.0214(16) -0.0001(18) O2 0.117(2) 0.089(2) 0.0387(15) -0.0034(15) 0.0323(16) -0.0213(19) C16 0.068(2) 0.048(2) 0.0384(18) -0.0024(15) 0.0209(16) -0.0043(18) C9 0.072(2) 0.049(2) 0.0395(19) -0.0047(16) 0.0247(17) -0.0044(18) C2 0.071(2) 0.046(2) 0.0406(19) -0.0027(16) 0.0214(17) -0.0001(18) C18 0.062(2) 0.056(2) 0.0397(19) 0.0015(16) 0.0191(16) -0.0017(17) C19 0.069(2) 0.054(3) 0.046(2) 0.0023(18) 0.0218(18) -0.003(2) C17 0.068(2) 0.046(2) 0.0382(19) -0.0018(15) 0.0193(17) -0.0040(18) C3 0.064(2) 0.054(3) 0.049(2) -0.0030(18) 0.0198(18) 0.0025(18) C1 0.073(2) 0.049(2) 0.0398(19) -0.0083(16) 0.0232(17) -0.0026(18) C10 0.075(2) 0.050(2) 0.046(2) -0.0025(16) 0.0284(18) -0.0006(18) N1 0.073(3) 0.055(2) 0.064(2) -0.0136(18) 0.0156(19) 0.0020(19) C21 0.069(2) 0.055(3) 0.048(2) -0.0033(18) 0.016(2) -0.0027(19) N3 0.093(3) 0.102(3) 0.057(2) -0.007(2) 0.038(2) -0.013(2) C20 0.065(2) 0.062(3) 0.045(2) -0.0075(18) 0.0180(19) -0.0060(19) C4 0.081(3) 0.064(3) 0.055(2) -0.012(2) 0.017(2) -0.013(2) C6 0.091(3) 0.059(3) 0.040(2) -0.0067(18) 0.027(2) -0.006(2) N4 0.091(3) 0.075(3) 0.057(2) 0.004(2) 0.015(2) 0.002(2) N2 0.081(2) 0.067(3) 0.069(2) -0.011(2) 0.023(2) -0.008(2) C14 0.072(3) 0.067(3) 0.051(2) -0.0012(19) 0.0240(19) -0.001(2) C5 0.101(3) 0.076(3) 0.039(2) -0.007(2) 0.020(2) -0.012(3) C11 0.094(3) 0.060(3) 0.074(3) -0.018(2) 0.044(2) -0.001(2) C12 0.099(3) 0.069(3) 0.079(3) -0.009(2) 0.045(3) 0.021(3) C13 0.083(3) 0.097(4) 0.060(3) -0.008(2) 0.031(2) 0.017(3) C7 0.128(4) 0.138(5) 0.040(2) 0.014(3) 0.026(3) -0.015(4) C8 0.072(3) 0.087(4) 0.086(3) -0.007(3) 0.033(3) -0.013(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 C3 1.377(5) . ? O1 C8 1.421(6) . ? C15 C16 1.479(6) . ? C15 C10 1.513(6) . ? C15 C14 1.331(6) . ? O2 C6 1.374(5) . ? O2 C7 1.422(5) . ? C16 C19 1.433(6) . ? C16 C17 1.356(6) . ? C9 H9 0.9800 . ? C9 C18 1.569(6) . ? C9 C1 1.529(5) . ? C9 C10 1.543(5) . ? C2 H2 0.9300 . ? C2 C3 1.394(6) . ? C2 C1 1.381(6) . ? C18 C17 1.536(5) . ? C18 C21 1.489(5) . ? C18 C20 1.489(6) . ? C19 N2 1.150(5) . ? C17 N1 1.361(6) . ? C3 C4 1.389(6) . ? C1 C6 1.406(5) . ? C10 H10 0.9800 . ? C10 C11 1.514(6) . ? N1 H11 0.94(5) . ? N1 H12 0.91(5) . ? C21 N4 1.131(5) . ? N3 C20 1.138(6) . ? C4 H4 0.9300 . ? C4 C5 1.377(7) . ? C6 C5 1.377(7) . ? C14 H14A 0.9300 . ? C14 C13 1.499(7) . ? C5 H5 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.522(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.517(8) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 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 C3 O1 C8 117.8(3) . . ? C16 C15 C10 115.5(3) . . ? C14 C15 C16 121.8(4) . . ? C14 C15 C10 122.7(4) . . ? C6 O2 C7 118.1(4) . . ? C19 C16 C15 117.8(3) . . ? C17 C16 C15 124.4(3) . . ? C17 C16 C19 117.8(4) . . ? C18 C9 H9 106.4 . . ? C1 C9 H9 106.4 . . ? C1 C9 C18 110.2(3) . . ? C1 C9 C10 115.8(3) . . ? C10 C9 H9 106.4 . . ? C10 C9 C18 111.1(3) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C1 C2 C3 121.9(3) . . ? C17 C18 C9 112.8(3) . . ? C21 C18 C9 108.4(3) . . ? C21 C18 C17 110.6(3) . . ? C20 C18 C9 111.5(3) . . ? C20 C18 C17 106.1(3) . . ? C20 C18 C21 107.3(3) . . ? N2 C19 C16 176.3(5) . . ? C16 C17 C18 120.3(4) . . ? C16 C17 N1 124.8(4) . . ? N1 C17 C18 114.8(3) . . ? O1 C3 C2 116.8(3) . . ? O1 C3 C4 124.2(4) . . ? C4 C3 C2 119.0(4) . . ? C2 C1 C9 122.2(3) . . ? C2 C1 C6 118.0(4) . . ? C6 C1 C9 119.8(4) . . ? C15 C10 C9 109.5(3) . . ? C15 C10 H10 107.9 . . ? C15 C10 C11 111.8(3) . . ? C9 C10 H10 107.9 . . ? C11 C10 C9 111.5(3) . . ? C11 C10 H10 107.9 . . ? C17 N1 H11 122(3) . . ? C17 N1 H12 118(3) . . ? H11 N1 H12 120(4) . . ? N4 C21 C18 178.4(5) . . ? N3 C20 C18 179.3(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 C3 119.7(4) . . ? C5 C4 H4 120.1 . . ? O2 C6 C1 114.5(4) . . ? O2 C6 C5 125.2(4) . . ? C5 C6 C1 120.3(4) . . ? C15 C14 H14A 117.8 . . ? C15 C14 C13 124.5(4) . . ? C13 C14 H14A 117.8 . . ? C4 C5 H5 119.5 . . ? C6 C5 C4 121.1(4) . . ? C6 C5 H5 119.5 . . ? C10 C11 H11A 109.2 . . ? C10 C11 H11B 109.2 . . ? C10 C11 C12 111.8(4) . . ? H11A C11 H11B 107.9 . . ? C12 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C13 C12 C11 110.5(4) . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? C14 C13 C12 110.4(4) . . ? C14 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? C12 C13 H13A 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C3 C4 C5 -176.7(4) . . . . ? C15 C16 C19 N2 -127(7) . . . . ? C15 C16 C17 C18 2.0(6) . . . . ? C15 C16 C17 N1 177.8(4) . . . . ? C15 C10 C11 C12 41.8(5) . . . . ? C15 C14 C13 C12 -17.7(6) . . . . ? O2 C6 C5 C4 178.3(5) . . . . ? C16 C15 C10 C9 44.2(4) . . . . ? C16 C15 C10 C11 168.4(3) . . . . ? C16 C15 C14 C13 179.5(4) . . . . ? C9 C18 C17 C16 -16.6(5) . . . . ? C9 C18 C17 N1 167.2(3) . . . . ? C9 C18 C21 N4 41(18) . . . . ? C9 C18 C20 N3 106(43) . . . . ? C9 C1 C6 O2 4.8(6) . . . . ? C9 C1 C6 C5 -176.0(4) . . . . ? C9 C10 C11 C12 164.9(4) . . . . ? C2 C3 C4 C5 1.0(7) . . . . ? C2 C1 C6 O2 -177.8(4) . . . . ? C2 C1 C6 C5 1.3(6) . . . . ? C18 C9 C1 C2 -80.0(5) . . . . ? C18 C9 C1 C6 97.2(4) . . . . ? C18 C9 C10 C15 -58.5(4) . . . . ? C18 C9 C10 C11 177.2(3) . . . . ? C19 C16 C17 C18 -176.2(3) . . . . ? C19 C16 C17 N1 -0.3(6) . . . . ? C17 C16 C19 N2 51(7) . . . . ? C17 C18 C21 N4 165(18) . . . . ? C17 C18 C20 N3 -17(43) . . . . ? C3 C2 C1 C9 176.6(4) . . . . ? C3 C2 C1 C6 -0.7(6) . . . . ? C3 C4 C5 C6 -0.4(8) . . . . ? C1 C9 C18 C17 174.5(3) . . . . ? C1 C9 C18 C21 -62.6(4) . . . . ? C1 C9 C18 C20 55.2(4) . . . . ? C1 C9 C10 C15 174.9(3) . . . . ? C1 C9 C10 C11 50.5(5) . . . . ? C1 C2 C3 O1 177.4(4) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C1 C6 C5 C4 -0.7(8) . . . . ? C10 C15 C16 C19 161.6(3) . . . . ? C10 C15 C16 C17 -16.5(5) . . . . ? C10 C15 C14 C13 -1.3(6) . . . . ? C10 C9 C18 C17 44.8(4) . . . . ? C10 C9 C18 C21 167.6(3) . . . . ? C10 C9 C18 C20 -74.5(4) . . . . ? C10 C9 C1 C2 47.2(5) . . . . ? C10 C9 C1 C6 -135.6(4) . . . . ? C10 C11 C12 C13 -62.2(5) . . . . ? C21 C18 C17 C16 -138.2(4) . . . . ? C21 C18 C17 N1 45.6(5) . . . . ? C21 C18 C20 N3 -135(43) . . . . ? C20 C18 C17 C16 105.8(4) . . . . ? C20 C18 C17 N1 -70.5(4) . . . . ? C20 C18 C21 N4 -79(18) . . . . ? C14 C15 C16 C19 -19.1(5) . . . . ? C14 C15 C16 C17 162.7(4) . . . . ? C14 C15 C10 C9 -135.0(4) . . . . ? C14 C15 C10 C11 -10.9(5) . . . . ? C11 C12 C13 C14 47.9(5) . . . . ? C7 O2 C6 C1 -177.2(5) . . . . ? C7 O2 C6 C5 3.8(7) . . . . ? C8 O1 C3 C2 152.3(4) . . . . ? C8 O1 C3 C4 -30.0(6) . . . . ? _olex2_submission_special_instructions 'No special instructions were received'