# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_aks-17 #TrackingRef 'AKS-17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 N2 O3' _chemical_formula_sum 'C18 H22 N2 O3' _chemical_formula_weight 314.38 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.0436(11) _cell_length_b 15.9764(17) _cell_length_c 17.130(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1654.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9812 _exptl_absorpt_correction_T_max 0.9829 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'oxford diffraction' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6291 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3369 _reflns_number_gt 2910 _reflns_threshold_expression >2\s(I) _computing_data_collection 'OXFORD DIFFRACTION' _computing_cell_refinement 'OXFORD DIFFRACTION' _computing_data_reduction 'OXFORD DIFFRACTION' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics MERCURY _computing_publication_material 'WINGX 1.80.01' _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^ > 2\s(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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(13) _refine_ls_number_reflns 3369 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.003 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 -0.1621(2) 0.05204(8) 0.34847(8) 0.0541(4) Uani 1 1 d . . . O2 O 0.4842(2) -0.04483(9) 0.24493(10) 0.0598(4) Uani 1 1 d . . . O3 O 0.4254(2) 0.12810(9) 0.13567(8) 0.0553(4) Uani 1 1 d . . . N1 N 0.1704(3) 0.02352(8) 0.28780(8) 0.0371(3) Uani 1 1 d . . . N2 N 0.1306(3) 0.04573(10) 0.11864(9) 0.0435(4) Uani 1 1 d . . . C1 C 0.1983(3) 0.10427(10) 0.24854(10) 0.0393(4) Uani 1 1 d . . . H1 H 0.0539 0.1322 0.2490 0.047 Uiso 1 1 calc R . . C2 C 0.3582(4) 0.16064(12) 0.29125(12) 0.0497(5) Uani 1 1 d . . . H2A H 0.4039 0.2049 0.2561 0.060 Uiso 1 1 calc R . . H2B H 0.4889 0.1283 0.3044 0.060 Uiso 1 1 calc R . . C3 C 0.2689(4) 0.20039(12) 0.36558(12) 0.0534(5) Uani 1 1 d . . . H3 H 0.2142 0.1555 0.3994 0.064 Uiso 1 1 calc R . . C4 C 0.0789(5) 0.25893(17) 0.34902(18) 0.0884(9) Uani 1 1 d . . . H4A H -0.0360 0.2291 0.3221 0.133 Uiso 1 1 calc R . . H4B H 0.1297 0.3044 0.3171 0.133 Uiso 1 1 calc R . . H4C H 0.0221 0.2805 0.3973 0.133 Uiso 1 1 calc R . . C5 C 0.4524(5) 0.24534(18) 0.40829(15) 0.0779(8) Uani 1 1 d . . . H5A H 0.5712 0.2070 0.4184 0.117 Uiso 1 1 calc R . . H5B H 0.3969 0.2669 0.4568 0.117 Uiso 1 1 calc R . . H5C H 0.5057 0.2908 0.3768 0.117 Uiso 1 1 calc R . . C6 C -0.0155(3) 0.00417(11) 0.33347(10) 0.0376(4) Uani 1 1 d . . . C7 C 0.0146(3) -0.08439(10) 0.35765(10) 0.0381(4) Uani 1 1 d . . . C8 C -0.1217(4) -0.13529(12) 0.40013(11) 0.0500(5) Uani 1 1 d . . . H8 H -0.2573 -0.1162 0.4187 0.060 Uiso 1 1 calc R . . C9 C -0.0504(4) -0.21653(13) 0.41459(13) 0.0583(6) Uani 1 1 d . . . H9 H -0.1402 -0.2530 0.4427 0.070 Uiso 1 1 calc R . . C10 C 0.1528(4) -0.24354(12) 0.38762(13) 0.0591(6) Uani 1 1 d . . . H10 H 0.1993 -0.2977 0.3990 0.071 Uiso 1 1 calc R . . C11 C 0.2889(4) -0.19190(11) 0.34400(11) 0.0498(5) Uani 1 1 d . . . H11 H 0.4249 -0.2105 0.3254 0.060 Uiso 1 1 calc R . . C12 C 0.2148(3) -0.11173(10) 0.32913(10) 0.0395(4) Uani 1 1 d . . . C13 C 0.3158(3) -0.04395(11) 0.28224(10) 0.0417(4) Uani 1 1 d . . . C14 C 0.2644(3) 0.09256(10) 0.16277(11) 0.0399(4) Uani 1 1 d . . . C15 C -0.0794(3) 0.00606(13) 0.14019(12) 0.0478(5) Uani 1 1 d . . . H15A H -0.1720 0.0441 0.1698 0.057 Uiso 1 1 calc R . . H15B H -0.0546 -0.0442 0.1707 0.057 Uiso 1 1 calc R . . C16 C -0.1823(4) -0.01434(15) 0.06234(12) 0.0568(5) Uani 1 1 d . . . H16A H -0.2687 0.0324 0.0429 0.068 Uiso 1 1 calc R . . H16B H -0.2766 -0.0633 0.0660 0.068 Uiso 1 1 calc R . . C17 C 0.0150(4) -0.03104(14) 0.01067(13) 0.0597(6) Uani 1 1 d . . . H17A H 0.0718 -0.0871 0.0188 0.072 Uiso 1 1 calc R . . H17B H -0.0233 -0.0243 -0.0440 0.072 Uiso 1 1 calc R . . C18 C 0.1808(4) 0.03362(14) 0.03570(11) 0.0548(5) Uani 1 1 d . . . H18A H 0.3309 0.0135 0.0285 0.066 Uiso 1 1 calc R . . H18B H 0.1618 0.0853 0.0067 0.066 Uiso 1 1 calc R . . 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 0.0475(8) 0.0527(7) 0.0622(9) 0.0052(6) 0.0180(7) 0.0138(7) O2 0.0480(8) 0.0581(8) 0.0732(10) 0.0008(7) 0.0222(8) 0.0073(8) O3 0.0520(9) 0.0624(8) 0.0514(8) 0.0002(7) 0.0116(7) -0.0156(7) N1 0.0402(8) 0.0352(7) 0.0360(7) 0.0011(6) 0.0070(7) 0.0025(7) N2 0.0431(9) 0.0495(8) 0.0378(8) -0.0012(6) 0.0066(7) -0.0037(8) C1 0.0434(9) 0.0343(8) 0.0401(9) 0.0011(7) 0.0055(8) 0.0037(9) C2 0.0574(12) 0.0426(9) 0.0493(11) -0.0024(8) 0.0042(10) -0.0042(10) C3 0.0714(15) 0.0460(10) 0.0428(10) -0.0020(8) 0.0022(10) -0.0061(11) C4 0.103(2) 0.0730(16) 0.089(2) -0.0306(15) -0.0041(18) 0.0264(16) C5 0.097(2) 0.0746(15) 0.0621(15) -0.0144(13) -0.0080(15) -0.0123(16) C6 0.0367(9) 0.0408(9) 0.0352(8) -0.0023(7) 0.0042(8) 0.0042(8) C7 0.0456(10) 0.0364(8) 0.0323(8) -0.0039(7) 0.0000(8) -0.0020(8) C8 0.0562(12) 0.0480(10) 0.0457(11) -0.0025(9) 0.0098(10) -0.0025(10) C9 0.0787(16) 0.0422(10) 0.0540(12) 0.0052(9) 0.0082(12) -0.0121(12) C10 0.0858(17) 0.0358(9) 0.0558(12) 0.0007(9) -0.0035(13) 0.0058(12) C11 0.0557(12) 0.0407(9) 0.0529(12) -0.0057(8) 0.0004(10) 0.0098(10) C12 0.0451(10) 0.0372(8) 0.0361(8) -0.0057(7) -0.0024(8) 0.0028(8) C13 0.0405(10) 0.0433(9) 0.0414(10) -0.0059(7) 0.0009(8) 0.0038(9) C14 0.0414(10) 0.0358(8) 0.0425(9) 0.0029(7) 0.0060(8) -0.0009(9) C15 0.0454(11) 0.0501(10) 0.0481(10) 0.0036(9) 0.0024(9) -0.0064(9) C16 0.0532(13) 0.0586(11) 0.0587(12) 0.0024(10) -0.0089(10) -0.0069(12) C17 0.0713(15) 0.0607(12) 0.0472(11) -0.0094(10) -0.0111(11) 0.0054(13) C18 0.0558(13) 0.0714(12) 0.0372(10) -0.0027(9) 0.0047(9) 0.0035(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.198(2) . ? O2 C13 1.202(2) . ? O3 C14 1.218(2) . ? N1 C13 1.394(2) . ? N1 C6 1.404(2) . ? N1 C1 1.465(2) . ? N2 C14 1.336(2) . ? N2 C18 1.466(2) . ? N2 C15 1.465(2) . ? C1 C2 1.510(3) . ? C1 C14 1.534(2) . ? C1 H1 0.9800 . ? C2 C3 1.522(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.508(4) . ? C3 C5 1.510(3) . ? C3 H3 0.9800 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.485(2) . ? C7 C8 1.367(3) . ? C7 C12 1.376(3) . ? C8 C9 1.390(3) . ? C8 H8 0.9300 . ? C9 C10 1.381(3) . ? C9 H9 0.9300 . ? C10 C11 1.384(3) . ? C10 H10 0.9300 . ? C11 C12 1.381(2) . ? C11 H11 0.9300 . ? C12 C13 1.480(3) . ? C15 C16 1.507(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.509(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.502(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? 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 N1 C6 111.85(14) . . ? C13 N1 C1 125.27(15) . . ? C6 N1 C1 122.83(14) . . ? C14 N2 C18 119.81(16) . . ? C14 N2 C15 128.58(15) . . ? C18 N2 C15 111.49(16) . . ? N1 C1 C2 112.12(15) . . ? N1 C1 C14 111.24(13) . . ? C2 C1 C14 111.74(15) . . ? N1 C1 H1 107.1 . . ? C2 C1 H1 107.1 . . ? C14 C1 H1 107.1 . . ? C1 C2 C3 115.30(17) . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C4 C3 C5 110.8(2) . . ? C4 C3 C2 111.81(19) . . ? C5 C3 C2 110.08(19) . . ? C4 C3 H3 108.0 . . ? C5 C3 H3 108.0 . . ? C2 C3 H3 108.0 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O1 C6 N1 124.80(15) . . ? O1 C6 C7 129.68(17) . . ? N1 C6 C7 105.52(14) . . ? C8 C7 C12 122.00(17) . . ? C8 C7 C6 129.90(18) . . ? C12 C7 C6 108.11(16) . . ? C7 C8 C9 117.6(2) . . ? C7 C8 H8 121.2 . . ? C9 C8 H8 121.2 . . ? C10 C9 C8 120.5(2) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 121.51(19) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C12 C11 C10 117.38(19) . . ? C12 C11 H11 121.3 . . ? C10 C11 H11 121.3 . . ? C7 C12 C11 120.96(18) . . ? C7 C12 C13 108.85(15) . . ? C11 C12 C13 130.17(18) . . ? O2 C13 N1 125.38(17) . . ? O2 C13 C12 129.00(17) . . ? N1 C13 C12 105.60(15) . . ? O3 C14 N2 121.92(17) . . ? O3 C14 C1 121.05(16) . . ? N2 C14 C1 116.92(15) . . ? N2 C15 C16 103.19(16) . . ? N2 C15 H15A 111.1 . . ? C16 C15 H15A 111.1 . . ? N2 C15 H15B 111.1 . . ? C16 C15 H15B 111.1 . . ? H15A C15 H15B 109.1 . . ? C15 C16 C17 103.36(17) . . ? C15 C16 H16A 111.1 . . ? C17 C16 H16A 111.1 . . ? C15 C16 H16B 111.1 . . ? C17 C16 H16B 111.1 . . ? H16A C16 H16B 109.1 . . ? C18 C17 C16 103.77(17) . . ? C18 C17 H17A 111.0 . . ? C16 C17 H17A 111.0 . . ? C18 C17 H17B 111.0 . . ? C16 C17 H17B 111.0 . . ? H17A C17 H17B 109.0 . . ? N2 C18 C17 103.27(17) . . ? N2 C18 H18A 111.1 . . ? C17 C18 H18A 111.1 . . ? N2 C18 H18B 111.1 . . ? C17 C18 H18B 111.1 . . ? H18A C18 H18B 109.1 . . ? 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 C13 N1 C1 C2 -80.4(2) . . . . ? C6 N1 C1 C2 102.56(19) . . . . ? C13 N1 C1 C14 45.6(2) . . . . ? C6 N1 C1 C14 -131.49(16) . . . . ? N1 C1 C2 C3 -74.9(2) . . . . ? C14 C1 C2 C3 159.44(16) . . . . ? C1 C2 C3 C4 -64.1(2) . . . . ? C1 C2 C3 C5 172.32(18) . . . . ? C13 N1 C6 O1 178.35(18) . . . . ? C1 N1 C6 O1 -4.2(3) . . . . ? C13 N1 C6 C7 -1.07(18) . . . . ? C1 N1 C6 C7 176.33(15) . . . . ? O1 C6 C7 C8 3.4(3) . . . . ? N1 C6 C7 C8 -177.21(18) . . . . ? O1 C6 C7 C12 -176.87(19) . . . . ? N1 C6 C7 C12 2.52(19) . . . . ? C12 C7 C8 C9 0.6(3) . . . . ? C6 C7 C8 C9 -179.71(19) . . . . ? C7 C8 C9 C10 1.0(3) . . . . ? C8 C9 C10 C11 -1.6(3) . . . . ? C9 C10 C11 C12 0.7(3) . . . . ? C8 C7 C12 C11 -1.5(3) . . . . ? C6 C7 C12 C11 178.73(16) . . . . ? C8 C7 C12 C13 176.80(16) . . . . ? C6 C7 C12 C13 -2.96(19) . . . . ? C10 C11 C12 C7 0.8(3) . . . . ? C10 C11 C12 C13 -177.09(18) . . . . ? C6 N1 C13 O2 177.82(18) . . . . ? C1 N1 C13 O2 0.5(3) . . . . ? C6 N1 C13 C12 -0.65(19) . . . . ? C1 N1 C13 C12 -177.98(15) . . . . ? C7 C12 C13 O2 -176.11(19) . . . . ? C11 C12 C13 O2 2.0(3) . . . . ? C7 C12 C13 N1 2.29(19) . . . . ? C11 C12 C13 N1 -179.61(18) . . . . ? C18 N2 C14 O3 2.2(3) . . . . ? C15 N2 C14 O3 -173.39(17) . . . . ? C18 N2 C14 C1 178.50(15) . . . . ? C15 N2 C14 C1 2.9(3) . . . . ? N1 C1 C14 O3 -127.90(18) . . . . ? C2 C1 C14 O3 -1.7(2) . . . . ? N1 C1 C14 N2 55.8(2) . . . . ? C2 C1 C14 N2 -178.06(15) . . . . ? C14 N2 C15 C16 163.38(18) . . . . ? C18 N2 C15 C16 -12.5(2) . . . . ? N2 C15 C16 C17 31.4(2) . . . . ? C15 C16 C17 C18 -39.2(2) . . . . ? C14 N2 C18 C17 172.12(17) . . . . ? C15 N2 C18 C17 -11.6(2) . . . . ? C16 C17 C18 N2 31.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.109 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.030 _database_code_depnum_ccdc_archive 'CCDC 895512' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_aks-20- #TrackingRef 'AKS-20-.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H20 N2 O3' _chemical_formula_sum 'C21 H20 N2 O3' _chemical_formula_weight 348.39 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_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' _cell_length_a 10.5272(10) _cell_length_b 11.4411(11) _cell_length_c 14.6077(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1759.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 26.37 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9799 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'oxford diffraction' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7499 _diffrn_reflns_av_R_equivalents 0.0131 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3593 _reflns_number_gt 3373 _reflns_threshold_expression >2\s(I) _computing_data_collection 'OXFORD DIFFRACTION' _computing_cell_refinement 'OXFORD DIFFRACTION' _computing_data_reduction 'OXFORD DIFFRACTION' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics MERCURY _computing_publication_material 'WINGX 1.80.01' _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^ > 2\s(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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.3225P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(13) _refine_ls_number_reflns 3593 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.23378(15) 0.67468(11) 0.16477(10) 0.0543(4) Uani 1 1 d . . . O2 O 0.22673(16) 0.29726(11) 0.06564(11) 0.0595(4) Uani 1 1 d . . . O3 O 0.45709(14) 0.27212(11) 0.21201(11) 0.0548(4) Uani 1 1 d . . . N1 N 0.25196(14) 0.47759(12) 0.13317(9) 0.0363(3) Uani 1 1 d . . . N2 N 0.54022(15) 0.43206(14) 0.14759(11) 0.0442(4) Uani 1 1 d . . . C1 C 0.32696(16) 0.44461(15) 0.21390(12) 0.0371(4) Uani 1 1 d . . . H1 H 0.3548 0.5170 0.2435 0.045 Uiso 1 1 calc R . . C2 C 0.24665(19) 0.37759(16) 0.28304(13) 0.0445(4) Uani 1 1 d . . . H2A H 0.2223 0.3032 0.2564 0.053 Uiso 1 1 calc R . . H2B H 0.2980 0.3614 0.3367 0.053 Uiso 1 1 calc R . . C3 C 0.12872(17) 0.44151(16) 0.31240(12) 0.0413(4) Uani 1 1 d . . . C4 C 0.1340(2) 0.5519(2) 0.35175(15) 0.0544(5) Uani 1 1 d . . . H4 H 0.2125 0.5874 0.3607 0.065 Uiso 1 1 calc R . . C5 C 0.0250(2) 0.6095(2) 0.37772(16) 0.0618(6) Uani 1 1 d . . . H5 H 0.0302 0.6835 0.4039 0.074 Uiso 1 1 calc R . . C6 C -0.0907(2) 0.5584(2) 0.36509(18) 0.0656(6) Uani 1 1 d . . . H6 H -0.1646 0.5978 0.3814 0.079 Uiso 1 1 calc R . . C7 C -0.0973(2) 0.4491(2) 0.3284(2) 0.0685(7) Uani 1 1 d . . . H7 H -0.1760 0.4133 0.3213 0.082 Uiso 1 1 calc R . . C8 C 0.0112(2) 0.39106(18) 0.30193(15) 0.0544(5) Uani 1 1 d . . . H8 H 0.0048 0.3167 0.2766 0.065 Uiso 1 1 calc R . . C9 C 0.20248(17) 0.59045(15) 0.12143(12) 0.0386(4) Uani 1 1 d . . . C10 C 0.10952(16) 0.58116(16) 0.04520(12) 0.0395(4) Uani 1 1 d . . . C11 C 0.0321(2) 0.66486(18) 0.00635(15) 0.0520(5) Uani 1 1 d . . . H11 H 0.0325 0.7417 0.0272 0.062 Uiso 1 1 calc R . . C12 C -0.0460(2) 0.6304(2) -0.06449(15) 0.0592(6) Uani 1 1 d . . . H12 H -0.0995 0.6850 -0.0917 0.071 Uiso 1 1 calc R . . C13 C -0.0464(2) 0.5171(2) -0.09564(14) 0.0578(5) Uani 1 1 d . . . H13 H -0.0992 0.4967 -0.1441 0.069 Uiso 1 1 calc R . . C14 C 0.03016(19) 0.43292(19) -0.05630(14) 0.0520(5) Uani 1 1 d . . . H14 H 0.0293 0.3560 -0.0769 0.062 Uiso 1 1 calc R . . C15 C 0.10789(16) 0.46720(16) 0.01465(13) 0.0404(4) Uani 1 1 d . . . C16 C 0.19976(17) 0.39890(15) 0.07121(12) 0.0405(4) Uani 1 1 d . . . C17 C 0.44665(17) 0.37466(15) 0.18940(12) 0.0387(4) Uani 1 1 d . . . C18 C 0.5440(2) 0.55543(18) 0.12053(17) 0.0557(5) Uani 1 1 d . . . H18A H 0.5037 0.6046 0.1662 0.067 Uiso 1 1 calc R . . H18B H 0.5025 0.5674 0.0620 0.067 Uiso 1 1 calc R . . C19 C 0.6819(3) 0.5798(2) 0.1143(3) 0.1031(12) Uani 1 1 d . . . H19A H 0.6988 0.6306 0.0625 0.124 Uiso 1 1 calc R . . H19B H 0.7105 0.6190 0.1695 0.124 Uiso 1 1 calc R . . C20 C 0.7486(3) 0.4713(3) 0.1033(2) 0.0855(8) Uani 1 1 d . . . H20A H 0.8244 0.4710 0.1410 0.103 Uiso 1 1 calc R . . H20B H 0.7738 0.4614 0.0399 0.103 Uiso 1 1 calc R . . C21 C 0.6628(2) 0.3748(2) 0.13124(17) 0.0573(5) Uani 1 1 d . . . H21A H 0.6558 0.3168 0.0831 0.069 Uiso 1 1 calc R . . H21B H 0.6936 0.3372 0.1865 0.069 Uiso 1 1 calc R . . 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 0.0639(9) 0.0322(6) 0.0668(9) -0.0041(6) -0.0109(8) 0.0006(6) O2 0.0786(10) 0.0340(7) 0.0659(9) -0.0075(6) -0.0164(8) 0.0056(7) O3 0.0530(8) 0.0396(7) 0.0718(9) 0.0096(7) 0.0095(7) 0.0107(6) N1 0.0390(7) 0.0309(7) 0.0391(8) 0.0009(6) -0.0027(6) 0.0021(6) N2 0.0413(8) 0.0401(8) 0.0511(9) -0.0034(7) 0.0066(7) 0.0052(7) C1 0.0376(8) 0.0356(8) 0.0382(9) -0.0001(7) -0.0033(7) 0.0048(7) C2 0.0451(9) 0.0446(9) 0.0436(9) 0.0084(8) 0.0029(8) 0.0086(8) C3 0.0431(9) 0.0454(10) 0.0354(9) 0.0067(7) 0.0016(7) 0.0024(8) C4 0.0507(11) 0.0559(12) 0.0565(12) -0.0077(9) 0.0006(9) -0.0024(9) C5 0.0692(15) 0.0524(12) 0.0637(13) -0.0096(10) 0.0136(11) 0.0069(11) C6 0.0512(12) 0.0676(15) 0.0781(16) 0.0014(12) 0.0186(11) 0.0113(11) C7 0.0444(12) 0.0701(16) 0.0911(18) -0.0087(13) 0.0103(11) -0.0068(11) C8 0.0510(11) 0.0498(11) 0.0625(12) -0.0054(9) 0.0089(10) -0.0042(9) C9 0.0393(9) 0.0334(9) 0.0431(9) 0.0045(7) 0.0003(7) -0.0003(7) C10 0.0376(9) 0.0388(9) 0.0421(9) 0.0064(7) 0.0035(7) 0.0009(8) C11 0.0508(11) 0.0489(11) 0.0561(11) 0.0111(9) 0.0009(10) 0.0077(9) C12 0.0438(11) 0.0754(15) 0.0583(12) 0.0216(11) -0.0042(9) 0.0111(11) C13 0.0390(10) 0.0897(17) 0.0446(11) 0.0077(11) -0.0064(9) 0.0005(11) C14 0.0457(10) 0.0610(12) 0.0494(11) -0.0049(9) -0.0034(9) -0.0042(10) C15 0.0371(9) 0.0443(9) 0.0400(9) 0.0042(8) 0.0005(7) -0.0007(7) C16 0.0429(9) 0.0369(9) 0.0416(9) 0.0024(7) -0.0029(7) -0.0001(7) C17 0.0409(9) 0.0376(9) 0.0377(8) -0.0020(7) -0.0013(7) 0.0034(7) C18 0.0573(12) 0.0433(10) 0.0664(13) 0.0032(9) 0.0122(10) -0.0033(10) C19 0.0708(17) 0.0562(15) 0.182(4) -0.0114(19) 0.035(2) -0.0158(13) C20 0.0528(14) 0.097(2) 0.107(2) 0.0271(17) 0.0150(14) -0.0034(14) C21 0.0456(11) 0.0605(13) 0.0657(13) -0.0093(11) 0.0098(10) 0.0079(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.199(2) . ? O2 C16 1.200(2) . ? O3 C17 1.224(2) . ? N1 C16 1.390(2) . ? N1 C9 1.403(2) . ? N1 C1 1.468(2) . ? N2 C17 1.332(2) . ? N2 C18 1.466(2) . ? N2 C21 1.467(2) . ? C1 C2 1.524(3) . ? C1 C17 1.535(2) . ? C1 H1 0.9800 . ? C2 C3 1.503(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.374(3) . ? C3 C4 1.389(3) . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 C6 1.364(4) . ? C5 H5 0.9300 . ? C6 C7 1.362(4) . ? C6 H6 0.9300 . ? C7 C8 1.377(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.486(3) . ? C10 C15 1.378(3) . ? C10 C11 1.380(3) . ? C11 C12 1.379(3) . ? C11 H11 0.9300 . ? C12 C13 1.374(3) . ? C12 H12 0.9300 . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C14 C15 1.377(3) . ? C14 H14 0.9300 . ? C15 C16 1.493(2) . ? C18 C19 1.481(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.435(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.483(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? 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 N1 C9 111.70(14) . . ? C16 N1 C1 124.69(14) . . ? C9 N1 C1 122.29(14) . . ? C17 N2 C18 128.18(16) . . ? C17 N2 C21 120.35(16) . . ? C18 N2 C21 111.22(16) . . ? N1 C1 C2 111.30(14) . . ? N1 C1 C17 112.84(14) . . ? C2 C1 C17 110.33(14) . . ? N1 C1 H1 107.4 . . ? C2 C1 H1 107.4 . . ? C17 C1 H1 107.4 . . ? C3 C2 C1 113.73(14) . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C8 C3 C4 117.68(18) . . ? C8 C3 C2 120.50(17) . . ? C4 C3 C2 121.82(18) . . ? C5 C4 C3 121.1(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 120.1(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 119.5(2) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 120.7(2) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C3 C8 C7 120.88(19) . . ? C3 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? O1 C9 N1 124.97(16) . . ? O1 C9 C10 129.34(16) . . ? N1 C9 C10 105.68(14) . . ? C15 C10 C11 121.06(18) . . ? C15 C10 C9 108.57(15) . . ? C11 C10 C9 130.36(18) . . ? C12 C11 C10 117.5(2) . . ? C12 C11 H11 121.2 . . ? C10 C11 H11 121.2 . . ? C13 C12 C11 121.3(2) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 121.2(2) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 117.5(2) . . ? C15 C14 H14 121.3 . . ? C13 C14 H14 121.3 . . ? C14 C15 C10 121.36(17) . . ? C14 C15 C16 130.71(18) . . ? C10 C15 C16 107.93(16) . . ? O2 C16 N1 125.34(17) . . ? O2 C16 C15 128.54(18) . . ? N1 C16 C15 106.11(15) . . ? O3 C17 N2 122.00(17) . . ? O3 C17 C1 120.71(16) . . ? N2 C17 C1 117.18(15) . . ? N2 C18 C19 103.0(2) . . ? N2 C18 H18A 111.2 . . ? C19 C18 H18A 111.2 . . ? N2 C18 H18B 111.2 . . ? C19 C18 H18B 111.2 . . ? H18A C18 H18B 109.1 . . ? C20 C19 C18 108.9(2) . . ? C20 C19 H19A 109.9 . . ? C18 C19 H19A 109.9 . . ? C20 C19 H19B 109.9 . . ? C18 C19 H19B 109.9 . . ? H19A C19 H19B 108.3 . . ? C19 C20 C21 108.4(2) . . ? C19 C20 H20A 110.0 . . ? C21 C20 H20A 110.0 . . ? C19 C20 H20B 110.0 . . ? C21 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? N2 C21 C20 104.36(19) . . ? N2 C21 H21A 110.9 . . ? C20 C21 H21A 110.9 . . ? N2 C21 H21B 110.9 . . ? C20 C21 H21B 110.9 . . ? H21A C21 H21B 108.9 . . ? 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 C16 N1 C1 C2 -65.3(2) . . . . ? C9 N1 C1 C2 100.54(18) . . . . ? C16 N1 C1 C17 59.4(2) . . . . ? C9 N1 C1 C17 -134.79(16) . . . . ? N1 C1 C2 C3 -55.3(2) . . . . ? C17 C1 C2 C3 178.68(15) . . . . ? C1 C2 C3 C8 123.3(2) . . . . ? C1 C2 C3 C4 -57.5(2) . . . . ? C8 C3 C4 C5 -1.2(3) . . . . ? C2 C3 C4 C5 179.58(19) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C5 C6 C7 1.4(4) . . . . ? C5 C6 C7 C8 -1.7(4) . . . . ? C4 C3 C8 C7 0.9(3) . . . . ? C2 C3 C8 C7 -179.9(2) . . . . ? C6 C7 C8 C3 0.5(4) . . . . ? C16 N1 C9 O1 -178.28(18) . . . . ? C1 N1 C9 O1 14.2(3) . . . . ? C16 N1 C9 C10 0.50(19) . . . . ? C1 N1 C9 C10 -166.98(14) . . . . ? O1 C9 C10 C15 178.13(19) . . . . ? N1 C9 C10 C15 -0.58(19) . . . . ? O1 C9 C10 C11 -2.5(3) . . . . ? N1 C9 C10 C11 178.80(19) . . . . ? C15 C10 C11 C12 -0.5(3) . . . . ? C9 C10 C11 C12 -179.84(19) . . . . ? C10 C11 C12 C13 -0.3(3) . . . . ? C11 C12 C13 C14 0.9(3) . . . . ? C12 C13 C14 C15 -0.7(3) . . . . ? C13 C14 C15 C10 -0.1(3) . . . . ? C13 C14 C15 C16 179.58(19) . . . . ? C11 C10 C15 C14 0.7(3) . . . . ? C9 C10 C15 C14 -179.81(17) . . . . ? C11 C10 C15 C16 -179.01(17) . . . . ? C9 C10 C15 C16 0.4(2) . . . . ? C9 N1 C16 O2 178.94(19) . . . . ? C1 N1 C16 O2 -13.9(3) . . . . ? C9 N1 C16 C15 -0.24(19) . . . . ? C1 N1 C16 C15 166.88(15) . . . . ? C14 C15 C16 O2 1.0(4) . . . . ? C10 C15 C16 O2 -179.3(2) . . . . ? C14 C15 C16 N1 -179.86(19) . . . . ? C10 C15 C16 N1 -0.1(2) . . . . ? C18 N2 C17 O3 -176.8(2) . . . . ? C21 N2 C17 O3 -3.1(3) . . . . ? C18 N2 C17 C1 -0.6(3) . . . . ? C21 N2 C17 C1 173.13(16) . . . . ? N1 C1 C17 O3 -113.28(19) . . . . ? C2 C1 C17 O3 11.9(2) . . . . ? N1 C1 C17 N2 70.4(2) . . . . ? C2 C1 C17 N2 -164.37(16) . . . . ? C17 N2 C18 C19 157.4(2) . . . . ? C21 N2 C18 C19 -16.8(3) . . . . ? N2 C18 C19 C20 20.9(4) . . . . ? C18 C19 C20 C21 -17.7(4) . . . . ? C17 N2 C21 C20 -168.0(2) . . . . ? C18 N2 C21 C20 6.7(3) . . . . ? C19 C20 C21 N2 6.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.168 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 895513' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_aks-34 #TrackingRef 'AKS-34.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 N2 O3' _chemical_formula_sum 'C22 H22 N2 O3' _chemical_formula_weight 362.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.3444(10) _cell_length_b 14.8943(19) _cell_length_c 10.1015(15) _cell_angle_alpha 90.00 _cell_angle_beta 101.140(12) _cell_angle_gamma 90.00 _cell_volume 936.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9813 _exptl_absorpt_correction_T_max 0.9830 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'oxford diffraction' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7004 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3805 _reflns_number_gt 3389 _reflns_threshold_expression >2\s(I) _computing_data_collection 'OXFORD DIFFRACTION' _computing_cell_refinement 'OXFORD DIFFRACTION' _computing_data_reduction 'OXFORD DIFFRACTION' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics MERCURY _computing_publication_material 'WINGX 1.80.01' _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^ > 2\s(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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.0040P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(10) _refine_ls_number_reflns 3805 _refine_ls_number_parameters 244 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.32857(18) 0.76808(8) 0.64123(12) 0.0496(3) Uani 1 1 d . . . O2 O 0.90519(18) 0.78121(11) 0.43386(13) 0.0708(4) Uani 1 1 d . . . O3 O 0.64433(19) 0.63387(9) 0.23808(12) 0.0551(3) Uani 1 1 d . . . N1 N 0.59618(18) 0.75718(9) 0.51589(12) 0.0364(3) Uani 1 1 d . . . N2 N 0.43386(19) 0.75641(10) 0.21773(13) 0.0413(3) Uani 1 1 d . . . C1 C 0.5185(3) 0.67759(10) 0.43739(16) 0.0387(4) Uani 1 1 d . . . H1 H 0.3662 0.6698 0.4407 0.046 Uiso 1 1 calc R . . C2 C 0.6396(3) 0.59366(12) 0.49852(18) 0.0528(4) Uani 1 1 d . . . H2A H 0.5845 0.5417 0.4449 0.063 Uiso 1 1 calc R . . H2B H 0.7905 0.5999 0.4947 0.063 Uiso 1 1 calc R . . C3 C 0.6183(3) 0.57817(11) 0.64219(17) 0.0453(4) Uani 1 1 d . . . C4 C 0.4322(3) 0.54347(13) 0.6741(2) 0.0562(5) Uani 1 1 d . . . H4 H 0.3190 0.5276 0.6050 0.067 Uiso 1 1 calc R . . C5 C 0.4112(4) 0.53192(14) 0.8068(2) 0.0641(5) Uani 1 1 d . . . H5 H 0.2851 0.5081 0.8263 0.077 Uiso 1 1 calc R . . C6 C 0.5751(4) 0.55548(14) 0.9089(2) 0.0650(6) Uani 1 1 d . . . H6 H 0.5611 0.5481 0.9982 0.078 Uiso 1 1 calc R . . C7 C 0.7588(4) 0.58975(15) 0.8799(2) 0.0686(6) Uani 1 1 d . . . H7 H 0.8705 0.6057 0.9498 0.082 Uiso 1 1 calc R . . C8 C 0.7822(3) 0.60126(14) 0.7477(2) 0.0579(5) Uani 1 1 d . . . H8 H 0.9095 0.6248 0.7296 0.070 Uiso 1 1 calc R . . C9 C 0.4962(2) 0.79427(10) 0.61545(15) 0.0361(3) Uani 1 1 d . . . C10 C 0.6351(2) 0.86903(11) 0.67556(16) 0.0381(3) Uani 1 1 d . . . C11 C 0.6097(3) 0.93015(12) 0.77421(18) 0.0491(4) Uani 1 1 d . . . H11 H 0.4919 0.9278 0.8164 0.059 Uiso 1 1 calc R . . C12 C 0.7668(3) 0.99492(13) 0.8074(2) 0.0605(5) Uani 1 1 d . . . H12 H 0.7550 1.0365 0.8743 0.073 Uiso 1 1 calc R . . C13 C 0.9410(3) 0.99968(13) 0.7441(2) 0.0627(5) Uani 1 1 d . . . H13 H 1.0428 1.0447 0.7680 0.075 Uiso 1 1 calc R . . C14 C 0.9656(3) 0.93815(13) 0.6454(2) 0.0559(5) Uani 1 1 d . . . H14 H 1.0833 0.9406 0.6031 0.067 Uiso 1 1 calc R . . C15 C 0.8098(2) 0.87326(12) 0.61196(16) 0.0418(4) Uani 1 1 d . . . C16 C 0.7883(2) 0.80088(12) 0.50988(16) 0.0437(4) Uani 1 1 d . . . C17 C 0.5378(2) 0.68794(11) 0.28816(16) 0.0397(4) Uani 1 1 d . . . C18 C 0.2705(2) 0.81375(12) 0.25863(17) 0.0449(4) Uani 1 1 d . . . H18A H 0.3151 0.8761 0.2587 0.054 Uiso 1 1 calc R . . H18B H 0.2545 0.7982 0.3494 0.054 Uiso 1 1 calc R . . C19 C 0.4610(3) 0.77193(13) 0.07892(17) 0.0490(4) Uani 1 1 d . . . H19A H 0.5696 0.7315 0.0578 0.059 Uiso 1 1 calc R . . H19B H 0.5099 0.8330 0.0703 0.059 Uiso 1 1 calc R . . C20 C 0.2531(3) 0.75714(15) -0.01939(18) 0.0563(5) Uani 1 1 d . . . H20A H 0.2114 0.6946 -0.0175 0.068 Uiso 1 1 calc R . . H20B H 0.2727 0.7712 -0.1100 0.068 Uiso 1 1 calc R . . C21 C 0.0782(3) 0.81578(16) 0.01639(19) 0.0637(5) Uani 1 1 d . . . H21A H -0.0573 0.8017 -0.0427 0.076 Uiso 1 1 calc R . . H21B H 0.1111 0.8783 0.0026 0.076 Uiso 1 1 calc R . . C22 C 0.0570(3) 0.80181(14) 0.16196(18) 0.0541(5) Uani 1 1 d . . . H22A H 0.0028 0.7418 0.1722 0.065 Uiso 1 1 calc R . . H22B H -0.0461 0.8444 0.1847 0.065 Uiso 1 1 calc R . . 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 0.0477(6) 0.0588(7) 0.0470(7) -0.0071(6) 0.0210(5) -0.0040(6) O2 0.0502(7) 0.1173(12) 0.0509(8) -0.0249(8) 0.0246(6) -0.0128(8) O3 0.0637(8) 0.0656(8) 0.0378(7) -0.0105(6) 0.0139(6) 0.0156(6) N1 0.0383(7) 0.0425(7) 0.0294(7) -0.0045(6) 0.0089(5) 0.0014(6) N2 0.0387(7) 0.0565(8) 0.0296(7) 0.0012(6) 0.0087(5) 0.0049(6) C1 0.0446(9) 0.0426(9) 0.0287(8) -0.0045(7) 0.0067(7) 0.0008(7) C2 0.0753(12) 0.0475(10) 0.0347(10) -0.0052(8) 0.0085(8) 0.0137(9) C3 0.0619(11) 0.0350(9) 0.0367(10) -0.0021(7) 0.0041(8) 0.0091(7) C4 0.0640(12) 0.0494(10) 0.0491(12) -0.0016(9) -0.0041(9) -0.0018(9) C5 0.0725(13) 0.0557(12) 0.0668(15) 0.0125(10) 0.0202(11) 0.0006(10) C6 0.0982(16) 0.0585(12) 0.0404(12) 0.0086(9) 0.0188(11) 0.0080(11) C7 0.0840(15) 0.0733(14) 0.0407(12) 0.0028(10) -0.0072(10) -0.0064(11) C8 0.0599(12) 0.0660(13) 0.0438(11) 0.0071(9) -0.0005(9) -0.0007(9) C9 0.0422(8) 0.0389(8) 0.0282(8) 0.0029(6) 0.0095(7) 0.0079(6) C10 0.0443(8) 0.0389(8) 0.0292(9) 0.0026(7) 0.0024(6) 0.0046(7) C11 0.0550(10) 0.0463(9) 0.0445(11) -0.0090(8) 0.0059(8) 0.0091(8) C12 0.0718(13) 0.0459(10) 0.0562(13) -0.0127(9) -0.0069(10) 0.0073(9) C13 0.0634(12) 0.0507(11) 0.0653(14) -0.0014(10) -0.0095(10) -0.0121(9) C14 0.0491(10) 0.0606(12) 0.0547(12) 0.0022(9) 0.0020(8) -0.0116(8) C15 0.0418(8) 0.0471(9) 0.0345(9) 0.0034(7) 0.0020(7) -0.0007(7) C16 0.0380(8) 0.0617(11) 0.0315(9) -0.0012(8) 0.0073(7) -0.0019(7) C17 0.0395(8) 0.0494(9) 0.0297(8) -0.0066(7) 0.0055(7) -0.0026(7) C18 0.0458(9) 0.0501(10) 0.0400(10) 0.0004(8) 0.0111(7) 0.0046(8) C19 0.0513(9) 0.0620(11) 0.0366(9) 0.0055(8) 0.0154(7) -0.0037(8) C20 0.0653(11) 0.0700(12) 0.0320(9) 0.0065(9) 0.0057(8) -0.0040(10) C21 0.0583(11) 0.0787(14) 0.0485(12) 0.0162(11) -0.0038(8) 0.0067(10) C22 0.0442(9) 0.0663(12) 0.0512(11) 0.0094(9) 0.0075(8) 0.0094(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.2073(18) . ? O2 C16 1.2025(18) . ? O3 C17 1.2222(19) . ? N1 C16 1.3932(19) . ? N1 C9 1.4021(18) . ? N1 C1 1.4581(19) . ? N2 C17 1.341(2) . ? N2 C18 1.4627(19) . ? N2 C19 1.464(2) . ? C1 C2 1.533(2) . ? C1 C17 1.544(2) . ? C1 H1 0.9800 . ? C2 C3 1.501(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.381(3) . ? C3 C4 1.383(3) . ? C4 C5 1.384(3) . ? C4 H4 0.9300 . ? C5 C6 1.362(3) . ? C5 H5 0.9300 . ? C6 C7 1.355(3) . ? C6 H6 0.9300 . ? C7 C8 1.382(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.476(2) . ? C10 C11 1.382(2) . ? C10 C15 1.386(2) . ? C11 C12 1.381(3) . ? C11 H11 0.9300 . ? C12 C13 1.381(3) . ? C12 H12 0.9300 . ? C13 C14 1.385(3) . ? C13 H13 0.9300 . ? C14 C15 1.377(2) . ? C14 H14 0.9300 . ? C15 C16 1.480(2) . ? C18 C22 1.519(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.506(2) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.510(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.517(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? 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 N1 C9 111.60(12) . . ? C16 N1 C1 124.25(13) . . ? C9 N1 C1 123.93(12) . . ? C17 N2 C18 126.62(13) . . ? C17 N2 C19 119.43(13) . . ? C18 N2 C19 113.53(13) . . ? N1 C1 C2 110.69(12) . . ? N1 C1 C17 111.58(13) . . ? C2 C1 C17 110.28(13) . . ? N1 C1 H1 108.1 . . ? C2 C1 H1 108.1 . . ? C17 C1 H1 108.1 . . ? C3 C2 C1 112.52(14) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C8 C3 C4 117.58(17) . . ? C8 C3 C2 120.86(18) . . ? C4 C3 C2 121.52(17) . . ? C3 C4 C5 121.25(19) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 119.9(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 119.8(2) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.9(2) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C3 C8 C7 120.61(19) . . ? C3 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? O1 C9 N1 124.54(14) . . ? O1 C9 C10 129.48(14) . . ? N1 C9 C10 105.98(12) . . ? C11 C10 C15 121.29(15) . . ? C11 C10 C9 130.55(15) . . ? C15 C10 C9 108.13(13) . . ? C12 C11 C10 117.13(17) . . ? C12 C11 H11 121.4 . . ? C10 C11 H11 121.4 . . ? C13 C12 C11 121.86(18) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 120.72(18) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 117.74(17) . . ? C15 C14 H14 121.1 . . ? C13 C14 H14 121.1 . . ? C14 C15 C10 121.26(16) . . ? C14 C15 C16 130.36(16) . . ? C10 C15 C16 108.38(13) . . ? O2 C16 N1 124.52(16) . . ? O2 C16 C15 129.58(15) . . ? N1 C16 C15 105.90(12) . . ? O3 C17 N2 122.41(15) . . ? O3 C17 C1 119.54(15) . . ? N2 C17 C1 118.05(13) . . ? N2 C18 C22 110.02(14) . . ? N2 C18 H18A 109.7 . . ? C22 C18 H18A 109.7 . . ? N2 C18 H18B 109.7 . . ? C22 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? N2 C19 C20 111.00(13) . . ? N2 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? N2 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C19 C20 C21 110.36(16) . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C20 C21 C22 111.08(15) . . ? C20 C21 H21A 109.4 . . ? C22 C21 H21A 109.4 . . ? C20 C21 H21B 109.4 . . ? C22 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C21 C22 C18 111.84(14) . . ? C21 C22 H22A 109.2 . . ? C18 C22 H22A 109.2 . . ? C21 C22 H22B 109.2 . . ? C18 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? 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 C16 N1 C1 C2 76.93(19) . . . . ? C9 N1 C1 C2 -97.12(17) . . . . ? C16 N1 C1 C17 -46.29(19) . . . . ? C9 N1 C1 C17 139.67(14) . . . . ? N1 C1 C2 C3 58.5(2) . . . . ? C17 C1 C2 C3 -177.59(15) . . . . ? C1 C2 C3 C8 -101.29(19) . . . . ? C1 C2 C3 C4 76.3(2) . . . . ? C8 C3 C4 C5 -0.3(3) . . . . ? C2 C3 C4 C5 -177.99(17) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C8 0.0(3) . . . . ? C4 C3 C8 C7 0.0(3) . . . . ? C2 C3 C8 C7 177.72(18) . . . . ? C6 C7 C8 C3 0.1(3) . . . . ? C16 N1 C9 O1 -179.56(15) . . . . ? C1 N1 C9 O1 -4.8(2) . . . . ? C16 N1 C9 C10 1.22(16) . . . . ? C1 N1 C9 C10 175.92(13) . . . . ? O1 C9 C10 C11 -1.7(3) . . . . ? N1 C9 C10 C11 177.45(16) . . . . ? O1 C9 C10 C15 -179.66(16) . . . . ? N1 C9 C10 C15 -0.48(16) . . . . ? C15 C10 C11 C12 -0.6(2) . . . . ? C9 C10 C11 C12 -178.30(17) . . . . ? C10 C11 C12 C13 0.8(3) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C13 C14 C15 C10 -0.5(3) . . . . ? C13 C14 C15 C16 178.24(17) . . . . ? C11 C10 C15 C14 0.5(2) . . . . ? C9 C10 C15 C14 178.64(15) . . . . ? C11 C10 C15 C16 -178.53(15) . . . . ? C9 C10 C15 C16 -0.37(17) . . . . ? C9 N1 C16 O2 179.25(16) . . . . ? C1 N1 C16 O2 4.6(3) . . . . ? C9 N1 C16 C15 -1.43(16) . . . . ? C1 N1 C16 C15 -176.12(13) . . . . ? C14 C15 C16 O2 1.5(3) . . . . ? C10 C15 C16 O2 -179.65(18) . . . . ? C14 C15 C16 N1 -177.80(17) . . . . ? C10 C15 C16 N1 1.08(17) . . . . ? C18 N2 C17 O3 167.19(15) . . . . ? C19 N2 C17 O3 -4.9(2) . . . . ? C18 N2 C17 C1 -12.2(2) . . . . ? C19 N2 C17 C1 175.69(13) . . . . ? N1 C1 C17 O3 121.57(16) . . . . ? C2 C1 C17 O3 -1.9(2) . . . . ? N1 C1 C17 N2 -59.00(18) . . . . ? C2 C1 C17 N2 177.55(14) . . . . ? C17 N2 C18 C22 -116.23(17) . . . . ? C19 N2 C18 C22 56.25(18) . . . . ? C17 N2 C19 C20 114.75(17) . . . . ? C18 N2 C19 C20 -58.3(2) . . . . ? N2 C19 C20 C21 55.9(2) . . . . ? C19 C20 C21 C22 -54.0(2) . . . . ? C20 C21 C22 C18 53.3(2) . . . . ? N2 C18 C22 C21 -53.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.124 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 895514'