# Electronic Supplementary Material (ESI) for Chemical Communications # 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_exp_810 _audit_creation_method SHELXL-97 _chemical_name_systematic unk _chemical_name_common ? _chemical_formula_moiety 'C24 H25 N O' _chemical_formula_sum 'C24 H25 N O' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 293(2) _chemical_formula_weight 343.45 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 'P b c a' _symmetry_int_tables_number 61 _chemical_absolute_configuration ? 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' '-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 15.2770(6) _cell_length_b 12.2434(5) _cell_length_c 20.3925(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3814.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10757 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0754 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 28.78 _reflns_number_total 4386 _reflns_number_gt 2091 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.2000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4386 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1561 _refine_ls_R_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.3194 _refine_ls_wR_factor_gt 0.2398 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O10 O 0.37183(15) 0.9597(2) 0.26872(11) 0.0647(7) Uani 1 1 d . . . N2 N 0.39824(16) 1.0326(2) 0.37616(12) 0.0464(7) Uani 1 1 d . . . C12 C 0.4470(2) 0.8474(3) 0.34903(16) 0.0512(8) Uani 1 1 d . . . C24 C 0.4496(2) 0.6498(3) 0.3270(2) 0.0655(10) Uani 1 1 d . . . C9 C 0.3998(2) 1.0542(3) 0.30762(16) 0.0530(8) Uani 1 1 d . . . H9 H 0.4603 1.0715 0.2954 0.064 Uiso 1 1 calc R . . C13 C 0.5554(2) 0.9934(3) 0.38922(14) 0.0486(8) Uani 1 1 d . . . C19 C 0.4724(2) 0.7401(3) 0.36770(18) 0.0541(9) Uani 1 1 d . . . C1 C 0.4627(2) 0.9467(2) 0.39161(14) 0.0470(8) Uani 1 1 d . . . H1 H 0.4520 0.9243 0.4370 0.056 Uiso 1 1 calc R . . C11 C 0.4014(2) 0.8614(3) 0.29108(17) 0.0561(9) Uani 1 1 d . . . C3 C 0.3106(2) 1.0152(3) 0.40463(17) 0.0546(9) Uani 1 1 d . . . H3A H 0.3103 0.9468 0.4286 0.066 Uiso 1 1 calc R . . H3B H 0.2681 1.0095 0.3695 0.066 Uiso 1 1 calc R . . C14 C 0.5716(2) 1.0914(3) 0.42043(16) 0.0630(10) Uani 1 1 d . . . H14 H 0.5265 1.1269 0.4424 0.076 Uiso 1 1 calc R . . C20 C 0.5196(2) 0.7189(3) 0.42587(18) 0.0647(10) Uani 1 1 d . . . H20 H 0.5349 0.7768 0.4531 0.078 Uiso 1 1 calc R . . C18 C 0.6244(2) 0.9419(3) 0.35756(17) 0.0602(9) Uani 1 1 d . . . H18 H 0.6150 0.8756 0.3364 0.072 Uiso 1 1 calc R . . C7 C 0.3629(2) 1.2578(3) 0.3144(2) 0.0690(11) Uani 1 1 d . . . H7A H 0.3256 1.3114 0.2933 0.083 Uiso 1 1 calc R . . H7B H 0.4229 1.2760 0.3033 0.083 Uiso 1 1 calc R . . C25 C 0.4027(3) 0.6698(3) 0.2687(2) 0.0730(12) Uani 1 1 d . . . H25 H 0.3874 0.6112 0.2420 0.088 Uiso 1 1 calc R . . C8 C 0.3424(2) 1.1471(3) 0.28483(18) 0.0651(10) Uani 1 1 d . . . H8A H 0.2820 1.1290 0.2949 0.078 Uiso 1 1 calc R . . H8B H 0.3473 1.1527 0.2375 0.078 Uiso 1 1 calc R . . C4 C 0.2839(3) 1.1067(3) 0.45034(19) 0.0689(10) Uani 1 1 d . . . H4A H 0.3276 1.1124 0.4846 0.083 Uiso 1 1 calc R . . H4B H 0.2291 1.0862 0.4711 0.083 Uiso 1 1 calc R . . C26 C 0.3792(2) 0.7720(3) 0.25046(19) 0.0696(11) Uani 1 1 d . . . H26 H 0.3487 0.7833 0.2116 0.084 Uiso 1 1 calc R . . C6 C 0.3523(3) 1.2707(3) 0.3883(2) 0.0719(11) Uani 1 1 d . . . H6A H 0.4037 1.2397 0.4091 0.086 Uiso 1 1 calc R . . H6B H 0.3519 1.3481 0.3982 0.086 Uiso 1 1 calc R . . C17 C 0.7071(2) 0.9881(4) 0.3571(2) 0.0794(13) Uani 1 1 d . . . H17 H 0.7526 0.9529 0.3355 0.095 Uiso 1 1 calc R . . C15 C 0.6550(3) 1.1374(4) 0.4193(2) 0.0789(13) Uani 1 1 d . . . H15 H 0.6649 1.2041 0.4398 0.095 Uiso 1 1 calc R . . C5 C 0.2721(3) 1.2198(3) 0.4197(2) 0.0723(11) Uani 1 1 d . . . H5A H 0.2266 1.2149 0.3867 0.087 Uiso 1 1 calc R . . H5B H 0.2512 1.2691 0.4535 0.087 Uiso 1 1 calc R . . C16 C 0.7223(3) 1.0853(4) 0.3883(2) 0.0837(14) Uani 1 1 d . . . H16 H 0.7781 1.1156 0.3884 0.100 Uiso 1 1 calc R . . C23 C 0.4758(3) 0.5444(3) 0.3465(3) 0.0825(13) Uani 1 1 d . . . H23 H 0.4616 0.4852 0.3199 0.099 Uiso 1 1 calc R . . C22 C 0.5209(3) 0.5262(3) 0.4023(3) 0.0900(15) Uani 1 1 d . . . H22 H 0.5370 0.4555 0.4138 0.108 Uiso 1 1 calc R . . C21 C 0.5434(3) 0.6146(4) 0.4430(2) 0.0799(12) Uani 1 1 d . . . H21 H 0.5744 0.6024 0.4816 0.096 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 O10 0.0665(16) 0.0735(17) 0.0541(14) -0.0093(12) -0.0109(11) 0.0083(13) N2 0.0415(14) 0.0525(16) 0.0452(14) -0.0006(11) 0.0038(11) 0.0002(12) C12 0.0462(17) 0.056(2) 0.0517(19) -0.0066(14) 0.0070(14) -0.0017(16) C24 0.059(2) 0.056(2) 0.082(3) -0.0115(18) 0.0275(19) -0.0068(18) C9 0.0486(17) 0.062(2) 0.0490(18) 0.0006(15) -0.0009(14) -0.0011(17) C13 0.0465(18) 0.0562(19) 0.0430(17) 0.0055(14) -0.0058(13) -0.0008(16) C19 0.0469(17) 0.053(2) 0.063(2) -0.0068(16) 0.0154(15) -0.0059(16) C1 0.0486(17) 0.0489(18) 0.0436(17) -0.0008(13) 0.0013(13) 0.0041(15) C11 0.0482(17) 0.064(2) 0.056(2) -0.0156(16) 0.0067(15) -0.0031(17) C3 0.0425(17) 0.057(2) 0.065(2) -0.0015(16) 0.0079(14) -0.0058(16) C14 0.058(2) 0.075(3) 0.055(2) -0.0023(17) -0.0139(16) -0.002(2) C20 0.072(2) 0.057(2) 0.065(2) 0.0044(17) 0.0152(18) 0.0042(19) C18 0.0506(19) 0.072(2) 0.058(2) 0.0078(17) 0.0010(15) 0.0068(18) C7 0.070(2) 0.058(2) 0.079(3) 0.0134(18) -0.0019(19) 0.0053(19) C25 0.057(2) 0.077(3) 0.085(3) -0.040(2) 0.014(2) -0.013(2) C8 0.058(2) 0.076(3) 0.061(2) 0.0105(18) -0.0067(16) 0.0073(19) C4 0.064(2) 0.072(3) 0.071(2) 0.0002(18) 0.0202(18) 0.006(2) C26 0.054(2) 0.084(3) 0.071(2) -0.031(2) 0.0002(17) 0.004(2) C6 0.074(3) 0.053(2) 0.088(3) -0.0029(19) -0.006(2) 0.005(2) C17 0.048(2) 0.106(4) 0.084(3) 0.017(2) 0.0023(19) 0.002(2) C15 0.073(3) 0.090(3) 0.074(3) 0.003(2) -0.027(2) -0.017(2) C5 0.073(2) 0.065(2) 0.079(3) -0.0061(19) 0.011(2) 0.016(2) C16 0.049(2) 0.114(4) 0.088(3) 0.022(3) -0.018(2) -0.020(3) C23 0.086(3) 0.057(2) 0.105(4) -0.014(2) 0.033(3) -0.012(2) C22 0.108(4) 0.051(2) 0.111(4) 0.010(2) 0.037(3) 0.004(2) C21 0.088(3) 0.069(3) 0.082(3) 0.016(2) 0.017(2) 0.008(2) _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 O10 C11 1.364(4) . ? O10 C9 1.467(4) . ? N2 C9 1.423(4) . ? N2 C3 1.474(4) . ? N2 C1 1.475(4) . ? C12 C11 1.383(5) . ? C12 C19 1.421(5) . ? C12 C1 1.514(4) . ? C24 C23 1.409(5) . ? C24 C25 1.410(6) . ? C24 C19 1.426(5) . ? C9 C8 1.509(5) . ? C13 C14 1.380(5) . ? C13 C18 1.388(4) . ? C13 C1 1.528(4) . ? C19 C20 1.412(5) . ? C11 C26 1.414(4) . ? C3 C4 1.513(5) . ? C14 C15 1.393(5) . ? C20 C21 1.374(5) . ? C18 C17 1.384(5) . ? C7 C8 1.516(5) . ? C7 C6 1.524(6) . ? C25 C26 1.354(5) . ? C4 C5 1.530(5) . ? C6 C5 1.517(5) . ? C17 C16 1.369(6) . ? C15 C16 1.365(6) . ? C23 C22 1.348(6) . ? C22 C21 1.407(6) . ? 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 C11 O10 C9 114.8(2) . . ? C9 N2 C3 115.4(3) . . ? C9 N2 C1 109.3(2) . . ? C3 N2 C1 114.8(2) . . ? C11 C12 C19 118.8(3) . . ? C11 C12 C1 118.0(3) . . ? C19 C12 C1 123.1(3) . . ? C23 C24 C25 122.8(4) . . ? C23 C24 C19 118.5(4) . . ? C25 C24 C19 118.7(3) . . ? N2 C9 O10 112.3(3) . . ? N2 C9 C8 115.6(3) . . ? O10 C9 C8 105.0(3) . . ? C14 C13 C18 118.3(3) . . ? C14 C13 C1 118.5(3) . . ? C18 C13 C1 123.3(3) . . ? C20 C19 C12 122.3(3) . . ? C20 C19 C24 118.1(3) . . ? C12 C19 C24 119.6(3) . . ? N2 C1 C12 110.2(2) . . ? N2 C1 C13 110.2(2) . . ? C12 C1 C13 115.4(2) . . ? O10 C11 C12 124.2(3) . . ? O10 C11 C26 114.1(3) . . ? C12 C11 C26 121.7(3) . . ? N2 C3 C4 112.4(3) . . ? C13 C14 C15 120.5(4) . . ? C21 C20 C19 121.3(4) . . ? C17 C18 C13 120.7(4) . . ? C8 C7 C6 117.6(3) . . ? C26 C25 C24 121.8(3) . . ? C9 C8 C7 115.5(3) . . ? C3 C4 C5 116.8(3) . . ? C25 C26 C11 119.4(4) . . ? C5 C6 C7 117.5(3) . . ? C16 C17 C18 120.5(4) . . ? C16 C15 C14 120.5(4) . . ? C6 C5 C4 116.7(3) . . ? C15 C16 C17 119.5(4) . . ? C22 C23 C24 122.3(4) . . ? C23 C22 C21 119.8(4) . . ? C20 C21 C22 120.0(4) . . ? _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 28.78 _diffrn_measured_fraction_theta_full 0.882 _refine_diff_density_max 0.143 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 952458' ####################################################################### # # 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_tst1 _audit_creation_method SHELXL-97 _chemical_name_systematic unk _chemical_name_common ? _chemical_formula_moiety 'C25 H21 N O' _chemical_formula_sum 'C25 H21 N O' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 296(2) _chemical_formula_weight 331.27 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 'P n a 21' _symmetry_int_tables_number 33 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 11.7114(6) _cell_length_b 17.5321(9) _cell_length_c 9.3005(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1909.63(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8121 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0677 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 21.53 _reflns_number_total 2158 _reflns_number_gt 2015 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.1670P)^2^+3.0691P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0066(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(2) _refine_ls_number_reflns 2158 _refine_ls_number_parameters 245 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 0.412 _refine_ls_restrained_S_all 0.411 _refine_ls_shift/su_max 0.165 _refine_ls_shift/su_mean 0.028 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 C6 C 0.1806(2) 0.60885(14) 0.5494(3) 0.0514(7) Uani 1 1 d . . . C4 C -0.0019(2) 0.61258(17) 0.6810(3) 0.0629(7) Uani 1 1 d . . . C1 C 0.1573(2) 0.53444(15) 0.5143(3) 0.0554(7) Uani 1 1 d . . . C5 C 0.1003(2) 0.64980(16) 0.6352(3) 0.0547(7) Uani 1 1 d . . . C7 C 0.1190(3) 0.72530(17) 0.6813(3) 0.0679(8) Uani 1 1 d . . . H7 H 0.1852 0.7506 0.6536 0.081 Uiso 1 1 calc R . . C3 C -0.0204(3) 0.53645(19) 0.6409(4) 0.0710(9) Uani 1 1 d . . . H3 H -0.0871 0.5121 0.6701 0.085 Uiso 1 1 calc R . . C2 C 0.0561(3) 0.49787(17) 0.5610(3) 0.0684(9) Uani 1 1 d . . . H2 H 0.0426 0.4472 0.5366 0.082 Uiso 1 1 calc R . . C10 C -0.0811(3) 0.6534(2) 0.7659(4) 0.0839(10) Uani 1 1 d . . . H10 H -0.1487 0.6298 0.7939 0.101 Uiso 1 1 calc R . . C8 C 0.0408(3) 0.7618(2) 0.7663(4) 0.0871(11) Uani 1 1 d . . . H8 H 0.0555 0.8113 0.7973 0.105 Uiso 1 1 calc R . . C9 C -0.0604(3) 0.7262(2) 0.8071(4) 0.0946(12) Uani 1 1 d . . . H9 H -0.1137 0.7523 0.8627 0.113 Uiso 1 1 calc R . . C24 C 0.2903(2) 0.64594(15) 0.4987(3) 0.0542(7) Uani 1 1 d . . . H24 H 0.3232 0.6728 0.5813 0.065 Uiso 1 1 calc R . . C18 C 0.2744(2) 0.70444(15) 0.3793(4) 0.0590(7) Uani 1 1 d . . . C12 C 0.5377(2) 0.50784(16) 0.5260(3) 0.0568(7) Uani 1 1 d . . . C11 C 0.4352(2) 0.55248(18) 0.5747(3) 0.0662(8) Uani 1 1 d . . . H11A H 0.3835 0.5189 0.6261 0.079 Uiso 1 1 calc R . . H11B H 0.4595 0.5922 0.6405 0.079 Uiso 1 1 calc R . . C13 C 0.6267(3) 0.5436(2) 0.4568(4) 0.0805(9) Uani 1 1 d . . . H13 H 0.6227 0.5954 0.4359 0.097 Uiso 1 1 calc R . . C17 C 0.5470(3) 0.43083(18) 0.5544(4) 0.0795(10) Uani 1 1 d . . . H17 H 0.4867 0.4058 0.5994 0.095 Uiso 1 1 calc R . . C19 C 0.1791(2) 0.70745(17) 0.2939(4) 0.0677(8) Uani 1 1 d . . . H19 H 0.1200 0.6729 0.3090 0.081 Uiso 1 1 calc R . . C23 C 0.3600(3) 0.75741(19) 0.3571(4) 0.0831(10) Uani 1 1 d . . . H23 H 0.4247 0.7569 0.4151 0.100 Uiso 1 1 calc R . . C20 C 0.1697(3) 0.7613(2) 0.1854(4) 0.0819(10) Uani 1 1 d . . . H20 H 0.1047 0.7624 0.1280 0.098 Uiso 1 1 calc R . . C22 C 0.3499(3) 0.8111(2) 0.2494(5) 0.1020(13) Uani 1 1 d . . . H22 H 0.4079 0.8465 0.2357 0.122 Uiso 1 1 calc R . . C21 C 0.2557(3) 0.8129(2) 0.1624(5) 0.0920(11) Uani 1 1 d . . . H21 H 0.2501 0.8486 0.0888 0.110 Uiso 1 1 calc R . . C15 C 0.7274(5) 0.4243(4) 0.4504(5) 0.1213(19) Uani 1 1 d . . . H15 H 0.7909 0.3956 0.4244 0.146 Uiso 1 1 calc R . . C14 C 0.7243(3) 0.5009(4) 0.4177(5) 0.1131(16) Uani 1 1 d . . . H14 H 0.7852 0.5240 0.3708 0.136 Uiso 1 1 calc R . . C16 C 0.6417(5) 0.3909(3) 0.5184(5) 0.1113(15) Uani 1 1 d . . . H16 H 0.6465 0.3394 0.5417 0.134 Uiso 1 1 calc R . . N1 N 0.37448(17) 0.58728(12) 0.4526(2) 0.0549(6) Uani 1 1 d . . . O1 O 0.22996(16) 0.48978(10) 0.4355(2) 0.0649(5) Uani 1 1 d . . . C25 C 0.3195(2) 0.53219(16) 0.3634(3) 0.0581(7) Uani 1 1 d . . . H25A H 0.3764 0.4965 0.3284 0.070 Uiso 1 1 calc R . . H25B H 0.2871 0.5580 0.2808 0.070 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 C6 0.0535(15) 0.0544(16) 0.0464(14) 0.0039(13) 0.0002(12) 0.0055(13) C4 0.0598(16) 0.0742(19) 0.0546(16) 0.0143(16) 0.0095(14) 0.0134(15) C1 0.0602(16) 0.0566(17) 0.0493(15) 0.0013(13) -0.0008(13) 0.0035(14) C5 0.0570(15) 0.0594(17) 0.0475(15) 0.0063(13) -0.0020(13) 0.0139(14) C7 0.076(2) 0.0617(19) 0.0656(18) 0.0015(16) -0.0001(17) 0.0177(15) C3 0.0650(18) 0.073(2) 0.075(2) 0.0135(17) 0.0085(17) -0.0036(16) C2 0.0735(19) 0.0618(18) 0.070(2) 0.0064(16) 0.0021(18) -0.0077(16) C10 0.080(2) 0.091(3) 0.081(2) 0.017(2) 0.021(2) 0.0204(19) C8 0.110(3) 0.070(2) 0.082(2) -0.0037(19) 0.007(2) 0.028(2) C9 0.098(3) 0.100(3) 0.086(2) 0.008(2) 0.027(2) 0.035(2) C24 0.0499(14) 0.0549(15) 0.0578(16) -0.0012(13) -0.0008(13) 0.0029(12) C18 0.0538(16) 0.0527(16) 0.0705(18) 0.0042(14) 0.0062(16) 0.0048(13) C12 0.0516(16) 0.0651(18) 0.0535(16) -0.0039(14) -0.0080(14) 0.0047(14) C11 0.0633(17) 0.0768(19) 0.0586(17) 0.0030(15) -0.0099(15) 0.0118(15) C13 0.067(2) 0.095(2) 0.079(2) 0.014(2) -0.0021(19) 0.0048(19) C17 0.085(2) 0.067(2) 0.087(2) -0.0096(18) -0.0254(19) 0.0039(18) C19 0.0559(16) 0.0711(19) 0.076(2) 0.0134(17) 0.0012(17) 0.0013(14) C23 0.0619(18) 0.081(2) 0.106(3) 0.027(2) -0.0011(19) -0.0030(17) C20 0.078(2) 0.084(2) 0.084(2) 0.025(2) 0.0026(19) 0.0211(19) C22 0.078(2) 0.086(2) 0.142(4) 0.047(3) 0.009(3) -0.003(2) C21 0.093(2) 0.081(2) 0.102(3) 0.040(2) 0.026(2) 0.021(2) C15 0.123(4) 0.173(5) 0.068(3) -0.031(3) -0.025(3) 0.085(4) C14 0.064(2) 0.204(5) 0.071(3) 0.013(3) 0.0002(19) 0.008(3) C16 0.144(4) 0.092(3) 0.098(3) -0.041(3) -0.042(3) 0.051(3) N1 0.0502(11) 0.0605(13) 0.0540(13) 0.0027(12) -0.0039(11) 0.0056(10) O1 0.0700(12) 0.0580(11) 0.0668(12) -0.0060(10) 0.0061(11) -0.0015(10) C25 0.0601(16) 0.0641(17) 0.0502(15) 0.0028(14) 0.0040(14) 0.0070(14) _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 C6 C1 1.372(4) . ? C6 C5 1.427(4) . ? C6 C24 1.514(4) . ? C4 C10 1.412(4) . ? C4 C3 1.403(5) . ? C4 C5 1.429(4) . ? C1 O1 1.369(3) . ? C1 C2 1.416(4) . ? C5 C7 1.408(4) . ? C7 C8 1.369(4) . ? C3 C2 1.347(4) . ? C10 C9 1.354(5) . ? C8 C9 1.393(5) . ? C24 N1 1.488(3) . ? C24 C18 1.523(4) . ? C18 C19 1.371(4) . ? C18 C23 1.381(4) . ? C12 C13 1.376(4) . ? C12 C17 1.380(4) . ? C12 C11 1.503(4) . ? C11 N1 1.472(4) . ? C13 C14 1.413(6) . ? C17 C16 1.354(5) . ? C19 C20 1.386(5) . ? C23 C22 1.379(5) . ? C20 C21 1.371(5) . ? C22 C21 1.368(6) . ? C15 C16 1.324(7) . ? C15 C14 1.377(8) . ? N1 C25 1.427(3) . ? O1 C25 1.450(4) . ? 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 C6 C5 118.7(2) . . ? C1 C6 C24 120.2(2) . . ? C5 C6 C24 121.1(2) . . ? C10 C4 C3 121.9(3) . . ? C10 C4 C5 119.1(3) . . ? C3 C4 C5 119.0(3) . . ? C6 C1 O1 123.2(2) . . ? C6 C1 C2 121.6(3) . . ? O1 C1 C2 115.2(2) . . ? C6 C5 C7 122.8(3) . . ? C6 C5 C4 119.3(3) . . ? C7 C5 C4 117.9(3) . . ? C8 C7 C5 120.8(3) . . ? C2 C3 C4 121.5(3) . . ? C3 C2 C1 120.0(3) . . ? C9 C10 C4 121.2(3) . . ? C7 C8 C9 121.1(3) . . ? C10 C9 C8 119.9(3) . . ? N1 C24 C6 110.8(2) . . ? N1 C24 C18 109.7(2) . . ? C6 C24 C18 114.4(2) . . ? C19 C18 C23 118.6(3) . . ? C19 C18 C24 123.2(2) . . ? C23 C18 C24 118.3(3) . . ? C13 C12 C17 118.4(3) . . ? C13 C12 C11 120.6(3) . . ? C17 C12 C11 121.0(3) . . ? N1 C11 C12 111.6(2) . . ? C12 C13 C14 119.4(4) . . ? C16 C17 C12 121.5(4) . . ? C18 C19 C20 120.8(3) . . ? C22 C23 C18 120.3(4) . . ? C19 C20 C21 120.3(3) . . ? C21 C22 C23 121.0(4) . . ? C22 C21 C20 119.0(3) . . ? C16 C15 C14 121.1(4) . . ? C15 C14 C13 118.8(4) . . ? C15 C16 C17 120.8(5) . . ? C25 N1 C11 112.7(2) . . ? C25 N1 C24 109.7(2) . . ? C11 N1 C24 112.6(2) . . ? C1 O1 C25 113.80(19) . . ? N1 C25 O1 113.9(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 21.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.121 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.024 _database_code_depnum_ccdc_archive 'CCDC 952459' ####################################################################### # # 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_ckj_132b _audit_creation_method SHELXL-97 _chemical_name_systematic rac-(7aS,12R)-12-Phenyl-7a,8,10,11-tetrahydro-12H-7,9-dioxa-11a-aza-benzo[a]anthracene _chemical_name_common ? _chemical_formula_moiety 'C21 H19 N O2' _chemical_formula_sum 'C21 H19 N O2' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 293(2) _chemical_formula_weight 317.37 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 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_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 16.6693(12) _cell_length_b 6.1313(3) _cell_length_c 17.7664(17) _cell_angle_alpha 90.00 _cell_angle_beta 115.984(11) _cell_angle_gamma 90.00 _cell_volume 1632.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5126 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2789 _reflns_number_gt 1946 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0400P)^2^+0.4000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2789 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1407 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O -0.16999(11) 0.3268(3) 0.33280(11) 0.0524(5) Uani 1 1 d . . . O1 O 0.00348(10) 0.1195(2) 0.39293(11) 0.0491(5) Uani 1 1 d . . . N1 N -0.01108(11) 0.4664(3) 0.32556(12) 0.0346(5) Uani 1 1 d . . . C1 C 0.13783(14) 0.3250(3) 0.42436(14) 0.0329(5) Uani 1 1 d . . . C12 C 0.10822(14) 0.4826(4) 0.28077(15) 0.0366(6) Uani 1 1 d . . . C9 C 0.23245(14) 0.3418(4) 0.47502(14) 0.0364(6) Uani 1 1 d . . . C18 C -0.03681(14) 0.2421(4) 0.31503(15) 0.0398(6) Uani 1 1 d . . . H18 H -0.0186 0.1762 0.2747 0.048 Uiso 1 1 calc R . . C11 C 0.08669(13) 0.4887(3) 0.35610(14) 0.0340(5) Uani 1 1 d . . . H11 H 0.1030 0.6341 0.3811 0.041 Uiso 1 1 calc R . . C2 C 0.09350(14) 0.1535(4) 0.43884(15) 0.0379(6) Uani 1 1 d . . . C10 C 0.27743(15) 0.1779(4) 0.53583(15) 0.0402(6) Uani 1 1 d . . . C8 C 0.28377(15) 0.5143(4) 0.46631(16) 0.0459(6) Uani 1 1 d . . . H8 H 0.2556 0.6248 0.4278 0.055 Uiso 1 1 calc R . . C21 C -0.04618(15) 0.5803(4) 0.37777(16) 0.0430(6) Uani 1 1 d . . . H21A H -0.0316 0.7342 0.3810 0.052 Uiso 1 1 calc R . . H21B H -0.0192 0.5209 0.4341 0.052 Uiso 1 1 calc R . . C13 C 0.15146(16) 0.3098(4) 0.26485(16) 0.0458(6) Uani 1 1 d . . . H13 H 0.1693 0.1913 0.3012 0.055 Uiso 1 1 calc R . . C4 C 0.22703(16) 0.0094(4) 0.54917(16) 0.0459(6) Uani 1 1 d . . . H4 H 0.2558 -0.0955 0.5900 0.055 Uiso 1 1 calc R . . C3 C 0.13711(16) -0.0009(4) 0.50304(16) 0.0438(6) Uani 1 1 d . . . H3 H 0.1043 -0.1092 0.5137 0.053 Uiso 1 1 calc R . . C20 C -0.14566(16) 0.5515(4) 0.33991(18) 0.0529(7) Uani 1 1 d . . . H20A H -0.1689 0.6255 0.3745 0.063 Uiso 1 1 calc R . . H20B H -0.1723 0.6182 0.2848 0.063 Uiso 1 1 calc R . . C19 C -0.13657(15) 0.2167(4) 0.28258(17) 0.0484(7) Uani 1 1 d . . . H19A H -0.1658 0.2732 0.2259 0.058 Uiso 1 1 calc R . . H19B H -0.1510 0.0629 0.2806 0.058 Uiso 1 1 calc R . . C6 C 0.41877(17) 0.3569(5) 0.57108(18) 0.0623(8) Uani 1 1 d . . . H6 H 0.4805 0.3613 0.6015 0.075 Uiso 1 1 calc R . . C17 C 0.08233(16) 0.6572(4) 0.22550(17) 0.0504(7) Uani 1 1 d . . . H17 H 0.0530 0.7752 0.2351 0.061 Uiso 1 1 calc R . . C7 C 0.37427(17) 0.5219(5) 0.51351(18) 0.0579(8) Uani 1 1 d . . . H7 H 0.4066 0.6383 0.5072 0.069 Uiso 1 1 calc R . . C5 C 0.37144(16) 0.1897(5) 0.58251(16) 0.0533(7) Uani 1 1 d . . . H5 H 0.4012 0.0816 0.6215 0.064 Uiso 1 1 calc R . . C16 C 0.09986(19) 0.6570(5) 0.15575(18) 0.0625(8) Uani 1 1 d . . . H16 H 0.0821 0.7744 0.1189 0.075 Uiso 1 1 calc R . . C15 C 0.14319(18) 0.4840(5) 0.14141(18) 0.0609(8) Uani 1 1 d . . . H15 H 0.1552 0.4848 0.0950 0.073 Uiso 1 1 calc R . . C14 C 0.16880(17) 0.3104(5) 0.19475(18) 0.0570(8) Uani 1 1 d . . . H14 H 0.1978 0.1927 0.1845 0.068 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 O2 0.0383(10) 0.0657(12) 0.0557(13) 0.0078(10) 0.0229(9) -0.0044(8) O1 0.0349(9) 0.0455(10) 0.0536(12) 0.0098(9) 0.0071(8) -0.0048(7) N1 0.0281(10) 0.0403(10) 0.0345(11) 0.0010(9) 0.0129(9) -0.0001(8) C1 0.0294(11) 0.0418(12) 0.0259(12) 0.0007(10) 0.0106(10) 0.0022(10) C12 0.0270(11) 0.0464(13) 0.0320(13) 0.0030(11) 0.0086(10) -0.0037(10) C9 0.0317(12) 0.0512(13) 0.0265(13) -0.0021(11) 0.0129(10) 0.0015(10) C18 0.0327(12) 0.0446(13) 0.0366(15) -0.0016(11) 0.0101(11) -0.0015(10) C11 0.0268(11) 0.0406(12) 0.0309(13) 0.0003(11) 0.0092(10) -0.0018(9) C2 0.0321(12) 0.0413(12) 0.0356(14) -0.0006(11) 0.0106(11) 0.0002(10) C10 0.0347(12) 0.0549(14) 0.0258(13) 0.0002(12) 0.0085(11) 0.0082(11) C8 0.0339(13) 0.0637(16) 0.0366(15) 0.0044(13) 0.0121(11) -0.0029(11) C21 0.0391(13) 0.0469(13) 0.0431(15) -0.0004(12) 0.0182(12) 0.0026(11) C13 0.0413(14) 0.0553(15) 0.0393(15) 0.0018(13) 0.0164(12) 0.0039(12) C4 0.0475(15) 0.0500(14) 0.0330(14) 0.0054(12) 0.0110(12) 0.0115(12) C3 0.0481(15) 0.0416(13) 0.0388(15) 0.0055(12) 0.0163(12) 0.0016(11) C20 0.0405(14) 0.0637(17) 0.0586(19) -0.0013(15) 0.0255(14) 0.0053(12) C19 0.0323(13) 0.0532(15) 0.0519(17) -0.0021(13) 0.0112(13) -0.0061(11) C6 0.0275(13) 0.100(2) 0.0461(17) 0.0029(17) 0.0040(13) 0.0019(14) C17 0.0461(15) 0.0577(16) 0.0480(17) 0.0141(14) 0.0211(13) 0.0074(12) C7 0.0360(14) 0.0819(19) 0.0503(18) 0.0002(16) 0.0139(13) -0.0111(14) C5 0.0392(14) 0.0782(19) 0.0333(15) 0.0061(14) 0.0073(12) 0.0137(13) C16 0.0592(18) 0.080(2) 0.0491(19) 0.0235(16) 0.0245(16) 0.0006(15) C15 0.0502(16) 0.099(2) 0.0379(16) 0.0006(17) 0.0235(14) -0.0123(16) C14 0.0496(16) 0.0763(19) 0.0486(18) -0.0086(16) 0.0248(14) 0.0041(14) _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 O2 C19 1.413(3) . ? O2 C20 1.426(3) . ? O1 C2 1.374(3) . ? O1 C18 1.455(3) . ? N1 C18 1.429(3) . ? N1 C21 1.472(3) . ? N1 C11 1.481(2) . ? C1 C2 1.373(3) . ? C1 C9 1.437(3) . ? C1 C11 1.516(3) . ? C12 C13 1.379(3) . ? C12 C17 1.387(3) . ? C12 C11 1.530(3) . ? C9 C8 1.411(3) . ? C9 C10 1.425(3) . ? C18 C19 1.511(3) . ? C2 C3 1.414(3) . ? C10 C4 1.415(3) . ? C10 C5 1.418(3) . ? C8 C7 1.368(3) . ? C21 C20 1.502(3) . ? C13 C14 1.396(3) . ? C4 C3 1.359(3) . ? C6 C5 1.362(4) . ? C6 C7 1.398(4) . ? C17 C16 1.392(4) . ? C16 C15 1.369(4) . ? C15 C14 1.363(4) . ? 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 C19 O2 C20 109.99(18) . . ? C2 O1 C18 114.53(17) . . ? C18 N1 C21 111.08(18) . . ? C18 N1 C11 110.84(16) . . ? C21 N1 C11 113.76(17) . . ? C2 C1 C9 118.1(2) . . ? C2 C1 C11 119.80(19) . . ? C9 C1 C11 122.11(19) . . ? C13 C12 C17 118.4(2) . . ? C13 C12 C11 122.8(2) . . ? C17 C12 C11 118.7(2) . . ? C8 C9 C10 118.0(2) . . ? C8 C9 C1 122.5(2) . . ? C10 C9 C1 119.5(2) . . ? N1 C18 O1 112.70(18) . . ? N1 C18 C19 111.48(18) . . ? O1 C18 C19 106.38(19) . . ? N1 C11 C1 112.00(17) . . ? N1 C11 C12 108.62(17) . . ? C1 C11 C12 114.72(18) . . ? C1 C2 O1 122.9(2) . . ? C1 C2 C3 122.4(2) . . ? O1 C2 C3 114.8(2) . . ? C4 C10 C5 121.6(2) . . ? C4 C10 C9 119.2(2) . . ? C5 C10 C9 119.1(2) . . ? C7 C8 C9 121.1(2) . . ? N1 C21 C20 109.1(2) . . ? C12 C13 C14 120.8(2) . . ? C3 C4 C10 120.8(2) . . ? C4 C3 C2 119.8(2) . . ? O2 C20 C21 111.6(2) . . ? O2 C19 C18 112.5(2) . . ? C5 C6 C7 119.8(2) . . ? C12 C17 C16 120.5(2) . . ? C8 C7 C6 120.9(3) . . ? C6 C5 C10 121.0(2) . . ? C15 C16 C17 120.0(3) . . ? C14 C15 C16 120.4(3) . . ? C15 C14 C13 119.9(3) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.216 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 952460' ####################################################################### # # 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_ckj_1_236_1 _audit_creation_method SHELXL-97 _chemical_name_systematic unk _chemical_name_common ? _chemical_formula_moiety 'C27 H25 N O2' _chemical_formula_sum 'C27 H25 N O2' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 293(2) _chemical_formula_weight 395.48 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 'C 2/c' _symmetry_int_tables_number 15 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.2548(11) _cell_length_b 9.6138(6) _cell_length_c 17.4876(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.593(4) _cell_angle_gamma 90.00 _cell_volume 4290.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10057 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 28.62 _reflns_number_total 4876 _reflns_number_gt 3100 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.2000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4876 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1019 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.2849 _refine_ls_wR_factor_gt 0.2272 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O0AA O 0.41340(7) 0.3831(2) 0.16607(9) 0.0509(5) Uani 1 1 d . . . H0AA H 0.3953 0.4336 0.1327 0.076 Uiso 1 1 calc R . . O1AA O 0.25407(7) 0.4571(2) -0.00869(9) 0.0556(6) Uani 1 1 d . . . N0AA N 0.33715(7) 0.5592(2) 0.11442(9) 0.0374(5) Uani 1 1 d . . . C0AA C 0.42547(9) 0.5251(3) 0.39379(12) 0.0411(6) Uani 1 1 d . . . C1AA C 0.25295(9) 0.5395(3) 0.16478(13) 0.0395(6) Uani 1 1 d . . . C2AA C 0.39700(8) 0.6074(3) 0.32989(12) 0.0376(6) Uani 1 1 d . . . C3AA C 0.36236(9) 0.6494(3) 0.18254(12) 0.0369(6) Uani 1 1 d . . . H3AA H 0.3346 0.6993 0.2000 0.044 Uiso 1 1 calc R . . C4AA C 0.39173(8) 0.5589(3) 0.25103(12) 0.0367(6) Uani 1 1 d . . . C5AA C 0.41558(9) 0.4363(3) 0.23884(12) 0.0401(6) Uani 1 1 d . . . C6AA C 0.39869(9) 0.7560(3) 0.16030(12) 0.0412(6) Uani 1 1 d . . . C7AA C 0.44787(9) 0.3979(3) 0.37725(14) 0.0479(7) Uani 1 1 d . . . H7AA H 0.4657 0.3426 0.4185 0.058 Uiso 1 1 calc R . . C8AA C 0.29556(9) 0.4682(3) 0.13280(12) 0.0391(6) Uani 1 1 d . . . H8AA H 0.3135 0.4046 0.1742 0.047 Uiso 1 1 calc R . . C9AA C 0.44367(10) 0.3559(3) 0.30245(15) 0.0467(6) Uani 1 1 d . . . H9AA H 0.4594 0.2732 0.2927 0.056 Uiso 1 1 calc R . . C0BA C 0.37649(10) 0.7360(3) 0.34925(14) 0.0470(7) Uani 1 1 d . . . H0BA H 0.3572 0.7915 0.3092 0.056 Uiso 1 1 calc R . . C1BA C 0.31673(10) 0.6397(3) 0.04178(13) 0.0448(6) Uani 1 1 d . . . H1B1 H 0.3448 0.6941 0.0292 0.054 Uiso 1 1 calc R . . H1B2 H 0.2898 0.7034 0.0498 0.054 Uiso 1 1 calc R . . C2BA C 0.25759(10) 0.5413(3) 0.24533(14) 0.0494(7) Uani 1 1 d . . . H2BA H 0.2872 0.5024 0.2783 0.059 Uiso 1 1 calc R . . C3BA C 0.20823(10) 0.5987(3) 0.11722(15) 0.0506(7) Uani 1 1 d . . . H3BA H 0.2042 0.6000 0.0629 0.061 Uiso 1 1 calc R . . C4BA C 0.43181(10) 0.5735(3) 0.47176(13) 0.0512(7) Uani 1 1 d . . . H4BA H 0.4496 0.5186 0.5132 0.061 Uiso 1 1 calc R . . C5BA C 0.29423(11) 0.5432(3) -0.02523(13) 0.0527(7) Uani 1 1 d . . . H5B1 H 0.2800 0.5976 -0.0721 0.063 Uiso 1 1 calc R . . H5B2 H 0.3220 0.4851 -0.0358 0.063 Uiso 1 1 calc R . . C6BA C 0.38446(11) 0.7798(4) 0.42560(15) 0.0543(7) Uani 1 1 d . . . H6BA H 0.3711 0.8651 0.4366 0.065 Uiso 1 1 calc R . . C7BA C 0.27401(12) 0.3776(3) 0.06072(14) 0.0516(7) Uani 1 1 d . . . H7B1 H 0.3017 0.3172 0.0520 0.062 Uiso 1 1 calc R . . H7B2 H 0.2462 0.3192 0.0710 0.062 Uiso 1 1 calc R . . C8BA C 0.41258(11) 0.6976(4) 0.48730(14) 0.0557(8) Uani 1 1 d . . . H8BA H 0.4180 0.7286 0.5390 0.067 Uiso 1 1 calc R . . C9BA C 0.21923(11) 0.5995(4) 0.27801(16) 0.0570(8) Uani 1 1 d . . . H9BA H 0.2234 0.6005 0.3323 0.068 Uiso 1 1 calc R . . C0CA C 0.17520(11) 0.6555(3) 0.23000(18) 0.0593(8) Uani 1 1 d . . . H0CA H 0.1491 0.6934 0.2516 0.071 Uiso 1 1 calc R . . C1CA C 0.44720(11) 0.7222(4) 0.14746(16) 0.0565(7) Uani 1 1 d . . . H1CA H 0.4586 0.6304 0.1532 0.068 Uiso 1 1 calc R . . C2CA C 0.16962(11) 0.6557(4) 0.14966(19) 0.0621(8) Uani 1 1 d . . . H2CA H 0.1398 0.6942 0.1171 0.074 Uiso 1 1 calc R . . C3CA C 0.38343(14) 0.8939(4) 0.15285(19) 0.0693(9) Uani 1 1 d . . . H3CA H 0.3509 0.9190 0.1610 0.083 Uiso 1 1 calc R . . C4CA C 0.47888(13) 0.8226(4) 0.1263(2) 0.0777(10) Uani 1 1 d . . . H4CA H 0.5109 0.7975 0.1164 0.093 Uiso 1 1 calc R . . C C 0.41576(18) 0.9956(4) 0.1334(3) 0.0963(14) Uani 1 1 d . . . H0 H 0.4052 1.0882 0.1295 0.116 Uiso 1 1 calc R . . C1 C 0.46338(18) 0.9587(5) 0.1198(3) 0.0956(13) Uani 1 1 d . . . H1 H 0.4851 1.0261 0.1062 0.115 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 O0AA 0.0574(11) 0.0522(13) 0.0393(9) -0.0079(8) 0.0040(8) 0.0161(10) O1AA 0.0590(11) 0.0630(14) 0.0372(9) -0.0062(9) -0.0040(8) -0.0014(10) N0AA 0.0394(10) 0.0428(13) 0.0272(9) 0.0017(8) 0.0021(7) 0.0040(9) C0AA 0.0342(11) 0.0502(16) 0.0355(11) 0.0030(10) 0.0014(9) -0.0060(11) C1AA 0.0384(11) 0.0382(14) 0.0403(12) 0.0005(10) 0.0059(9) -0.0046(11) C2AA 0.0343(11) 0.0453(15) 0.0319(10) -0.0004(10) 0.0053(8) -0.0037(11) C3AA 0.0382(11) 0.0399(14) 0.0312(10) -0.0013(9) 0.0054(8) 0.0030(10) C4AA 0.0325(11) 0.0431(15) 0.0324(11) 0.0013(10) 0.0035(8) -0.0007(10) C5AA 0.0353(11) 0.0443(16) 0.0375(11) -0.0034(10) 0.0024(9) 0.0030(11) C6AA 0.0470(13) 0.0397(14) 0.0360(12) 0.0006(10) 0.0078(9) 0.0015(11) C7AA 0.0390(12) 0.0525(17) 0.0446(13) 0.0080(12) -0.0055(10) -0.0015(12) C8AA 0.0414(12) 0.0379(14) 0.0346(11) 0.0014(9) 0.0022(9) 0.0029(11) C9AA 0.0396(12) 0.0439(16) 0.0513(14) 0.0035(11) -0.0003(10) 0.0067(12) C0BA 0.0486(14) 0.0501(17) 0.0408(12) -0.0041(11) 0.0077(10) 0.0017(13) C1BA 0.0459(13) 0.0531(17) 0.0323(11) 0.0068(11) 0.0032(9) 0.0067(12) C2BA 0.0434(13) 0.0582(19) 0.0441(13) -0.0002(12) 0.0052(10) -0.0039(13) C3BA 0.0497(14) 0.0557(18) 0.0455(13) 0.0069(12) 0.0096(10) 0.0058(14) C4BA 0.0488(14) 0.066(2) 0.0347(12) 0.0038(12) 0.0023(10) -0.0135(14) C5BA 0.0575(15) 0.064(2) 0.0326(11) -0.0002(12) 0.0026(10) 0.0103(15) C6BA 0.0588(16) 0.0598(19) 0.0470(14) -0.0112(13) 0.0177(11) -0.0019(15) C7BA 0.0582(15) 0.0477(17) 0.0440(13) -0.0058(11) 0.0019(11) 0.0049(13) C8BA 0.0645(17) 0.071(2) 0.0315(12) -0.0087(12) 0.0123(11) -0.0130(16) C9BA 0.0544(16) 0.066(2) 0.0530(15) -0.0078(14) 0.0179(12) -0.0074(15) C0CA 0.0512(15) 0.058(2) 0.0738(18) -0.0079(15) 0.0247(13) -0.0011(14) C1CA 0.0499(15) 0.0541(19) 0.0669(17) 0.0066(14) 0.0165(12) 0.0033(14) C2CA 0.0475(15) 0.067(2) 0.0723(18) 0.0092(16) 0.0144(12) 0.0131(15) C3CA 0.081(2) 0.0467(19) 0.093(2) 0.0126(17) 0.0461(18) 0.0107(17) C4CA 0.0579(19) 0.077(3) 0.106(3) 0.014(2) 0.0340(17) -0.0047(19) C 0.131(4) 0.044(2) 0.136(3) 0.019(2) 0.075(3) 0.008(2) C1 0.098(3) 0.070(3) 0.137(3) 0.015(3) 0.063(3) -0.016(2) _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 O0AA C5AA 1.360(3) . ? O1AA C5BA 1.423(3) . ? O1AA C7BA 1.426(3) . ? N0AA C1BA 1.477(3) . ? N0AA C8AA 1.492(3) . ? N0AA C3AA 1.496(3) . ? C0AA C4BA 1.413(3) . ? C0AA C7AA 1.415(4) . ? C0AA C2AA 1.429(3) . ? C1AA C2BA 1.385(3) . ? C1AA C3BA 1.391(3) . ? C1AA C8AA 1.526(3) . ? C2AA C0BA 1.420(4) . ? C2AA C4AA 1.431(3) . ? C3AA C6AA 1.512(3) . ? C3AA C4AA 1.534(3) . ? C4AA C5AA 1.375(4) . ? C5AA C9AA 1.412(3) . ? C6AA C3CA 1.382(4) . ? C6AA C1CA 1.383(4) . ? C7AA C9AA 1.349(4) . ? C8AA C7BA 1.527(3) . ? C0BA C6BA 1.368(3) . ? C1BA C5BA 1.503(4) . ? C2BA C9BA 1.388(4) . ? C3BA C2CA 1.386(4) . ? C4BA C8BA 1.348(4) . ? C6BA C8BA 1.400(4) . ? C9BA C0CA 1.369(4) . ? C0CA C2CA 1.378(4) . ? C1CA C4CA 1.380(4) . ? C3CA C 1.389(5) . ? C4CA C1 1.367(6) . ? C C1 1.373(6) . ? 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 C5BA O1AA C7BA 110.1(2) . . ? C1BA N0AA C8AA 110.89(17) . . ? C1BA N0AA C3AA 112.6(2) . . ? C8AA N0AA C3AA 112.19(16) . . ? C4BA C0AA C7AA 121.4(2) . . ? C4BA C0AA C2AA 119.5(3) . . ? C7AA C0AA C2AA 119.0(2) . . ? C2BA C1AA C3BA 117.6(2) . . ? C2BA C1AA C8AA 118.8(2) . . ? C3BA C1AA C8AA 123.6(2) . . ? C0BA C2AA C0AA 117.0(2) . . ? C0BA C2AA C4AA 123.8(2) . . ? C0AA C2AA C4AA 119.1(2) . . ? N0AA C3AA C6AA 112.08(17) . . ? N0AA C3AA C4AA 109.9(2) . . ? C6AA C3AA C4AA 110.71(18) . . ? C5AA C4AA C2AA 119.0(2) . . ? C5AA C4AA C3AA 121.95(19) . . ? C2AA C4AA C3AA 119.0(2) . . ? O0AA C5AA C4AA 123.2(2) . . ? O0AA C5AA C9AA 115.5(2) . . ? C4AA C5AA C9AA 121.3(2) . . ? C3CA C6AA C1CA 117.9(3) . . ? C3CA C6AA C3AA 119.2(2) . . ? C1CA C6AA C3AA 122.9(3) . . ? C9AA C7AA C0AA 120.9(2) . . ? N0AA C8AA C1AA 116.9(2) . . ? N0AA C8AA C7BA 107.73(19) . . ? C1AA C8AA C7BA 113.4(2) . . ? C7AA C9AA C5AA 120.6(3) . . ? C6BA C0BA C2AA 121.4(3) . . ? N0AA C1BA C5BA 110.1(2) . . ? C1AA C2BA C9BA 121.7(2) . . ? C2CA C3BA C1AA 120.9(2) . . ? C8BA C4BA C0AA 121.4(2) . . ? O1AA C5BA C1BA 112.0(2) . . ? C0BA C6BA C8BA 120.7(3) . . ? O1AA C7BA C8AA 112.8(2) . . ? C4BA C8BA C6BA 119.9(2) . . ? C0CA C9BA C2BA 119.7(3) . . ? C9BA C0CA C2CA 119.8(3) . . ? C4CA C1CA C6AA 121.0(3) . . ? C0CA C2CA C3BA 120.3(3) . . ? C6AA C3CA C 121.2(3) . . ? C1 C4CA C1CA 120.4(3) . . ? C1 C C3CA 119.6(4) . . ? C4CA C1 C 119.9(4) . . ? _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 28.62 _diffrn_measured_fraction_theta_full 0.889 _refine_diff_density_max 0.200 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 952461' ####################################################################### # # 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_sh-36-tri _audit_creation_method SHELXL-97 _chemical_name_systematic rac-(7aS,11R)-11-(4-Methoxy-phenyl)-7a.8,9,10-tetrahydro-11H-7-oxa-10a-aza-cyclopenta[b]phenanthrene _chemical_name_common ? _chemical_formula_moiety 'C22 H21 N O2' _chemical_formula_sum 'C22 H21 N O2' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 296(2) _chemical_formula_weight 331.40 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.5142(6) _cell_length_b 8.4766(7) _cell_length_c 32.727(3) _cell_angle_alpha 89.968(6) _cell_angle_beta 89.725(6) _cell_angle_gamma 72.066(6) _cell_volume 1719.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14886 _diffrn_reflns_av_R_equivalents 0.1751 _diffrn_reflns_av_sigmaI/netI 0.0862 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 0.62 _diffrn_reflns_theta_max 19.90 _reflns_number_total 3126 _reflns_number_gt 2306 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0884P)^2^+1.9789P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3126 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.2190 _refine_ls_wR_factor_gt 0.2107 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.003 _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 C2 C 0.5360(10) 0.1699(8) 0.29169(18) 0.0456(16) Uani 1 1 d . . . C3 C 0.4005(9) 0.6259(7) 0.17976(17) 0.0394(15) Uani 1 1 d . . . C1 C 0.4002(9) 0.1256(7) 0.32048(17) 0.0416(15) Uani 1 1 d . . . C12 C 0.4800(10) 0.4768(7) 0.15575(17) 0.0420(15) Uani 1 1 d . . . C8 C 0.5332(11) 0.6707(8) 0.20808(18) 0.0473(16) Uani 1 1 d . . . C10 C 0.8250(10) 0.4275(9) 0.1901(2) 0.0577(18) Uani 1 1 d . . . H10 H 0.9660 0.3595 0.1937 0.069 Uiso 1 1 calc R . . C11 C 0.6890(11) 0.3850(8) 0.16127(19) 0.0478(16) Uani 1 1 d . . . C7 C 0.4538(12) 0.8181(8) 0.23143(19) 0.0562(18) Uani 1 1 d . . . H7 H 0.5431 0.8468 0.2502 0.067 Uiso 1 1 calc R . . C5 C 0.1124(11) 0.8732(8) 0.1991(2) 0.0603(18) Uani 1 1 d . . . H5 H -0.0292 0.9411 0.1962 0.072 Uiso 1 1 calc R . . C4 C 0.1857(10) 0.7302(8) 0.17623(18) 0.0511(17) Uani 1 1 d . . . H4 H 0.0925 0.7021 0.1582 0.061 Uiso 1 1 calc R . . C6 C 0.2483(13) 0.9169(8) 0.2265(2) 0.0651(19) Uani 1 1 d . . . H6 H 0.1977 1.0144 0.2415 0.078 Uiso 1 1 calc R . . C9 C 0.7466(11) 0.5690(9) 0.2124(2) 0.0560(18) Uani 1 1 d . . . H9 H 0.8366 0.5987 0.2308 0.067 Uiso 1 1 calc R . . C13 C 0.3341(9) 0.4210(7) 0.12726(17) 0.0441(16) Uani 1 1 d . . . H13 H 0.2043 0.4239 0.1429 0.053 Uiso 1 1 calc R . . C14 C 0.2594(10) 0.5283(6) 0.08951(17) 0.0409(15) Uani 1 1 d . . . C17 C 0.1191(11) 0.7110(7) 0.0182(2) 0.0529(17) Uani 1 1 d . . . C19 C -0.0196(11) 0.6472(8) 0.0398(2) 0.0580(18) Uani 1 1 d . . . H19 H -0.1599 0.6638 0.0308 0.070 Uiso 1 1 calc R . . C18 C 0.0534(10) 0.5581(7) 0.0751(2) 0.0507(16) Uani 1 1 d . . . H18 H -0.0413 0.5165 0.0897 0.061 Uiso 1 1 calc R . . C15 C 0.3944(10) 0.5955(8) 0.0677(2) 0.0578(18) Uani 1 1 d . . . H15 H 0.5337 0.5812 0.0770 0.069 Uiso 1 1 calc R . . C16 C 0.3235(11) 0.6843(8) 0.0320(2) 0.0621(19) Uani 1 1 d . . . H16 H 0.4177 0.7261 0.0173 0.074 Uiso 1 1 calc R . . C20 C 0.6598(11) 0.2067(7) 0.1061(2) 0.0581(18) Uani 1 1 d . . . H20 H 0.6856 0.2628 0.0813 0.070 Uiso 1 1 calc R . . C21 C 0.7324(13) 0.0205(8) 0.0999(2) 0.083(2) Uani 1 1 d . . . H21A H 0.8801 -0.0287 0.1089 0.099 Uiso 1 1 calc R . . H21B H 0.7219 -0.0074 0.0714 0.099 Uiso 1 1 calc R . . C22 C 0.4146(11) 0.1187(8) 0.1429(2) 0.068(2) Uani 1 1 d . . . H22A H 0.2697 0.1098 0.1425 0.081 Uiso 1 1 calc R . . H22B H 0.4500 0.1414 0.1705 0.081 Uiso 1 1 calc R . . C23 C 0.5776(13) -0.0380(9) 0.1262(3) 0.088(2) Uani 1 1 d . . . H23A H 0.6539 -0.1072 0.1484 0.105 Uiso 1 1 calc R . . H23B H 0.5060 -0.1011 0.1100 0.105 Uiso 1 1 calc R . . C24 C -0.1505(13) 0.8504(9) -0.0303(2) 0.085(2) Uani 1 1 d . . . H24A H -0.1941 0.7542 -0.0358 0.127 Uiso 1 1 calc R . . H24B H -0.1645 0.9160 -0.0547 0.127 Uiso 1 1 calc R . . H24C H -0.2406 0.9151 -0.0092 0.127 Uiso 1 1 calc R . . O1 O 0.7848(7) 0.2396(5) 0.14021(14) 0.0662(13) Uani 1 1 d . . . O2 O 0.0666(8) 0.8005(6) -0.01741(14) 0.0768(14) Uani 1 1 d . . . N1 N 0.4353(8) 0.2478(6) 0.11435(14) 0.0501(14) Uani 1 1 d . . . O3 O 0.7853(7) -0.2608(5) 0.35985(14) 0.0659(13) Uani 1 1 d . . . C32 C 0.4816(10) -0.0227(7) 0.34414(16) 0.0398(15) Uani 1 1 d . . . C30 C 0.8254(10) -0.0725(9) 0.3099(2) 0.0575(18) Uani 1 1 d . . . H30 H 0.9666 -0.1404 0.3062 0.069 Uiso 1 1 calc R . . C28 C 0.4569(12) 0.3161(9) 0.2689(2) 0.0590(18) Uani 1 1 d . . . H28 H 0.5483 0.3454 0.2505 0.071 Uiso 1 1 calc R . . C31 C 0.6898(10) -0.1159(8) 0.33876(19) 0.0484(16) Uani 1 1 d . . . C26 C 0.1128(11) 0.3733(8) 0.3009(2) 0.0621(18) Uani 1 1 d . . . H26 H -0.0285 0.4417 0.3040 0.074 Uiso 1 1 calc R . . C25 C 0.1863(10) 0.2311(8) 0.32354(18) 0.0507(17) Uani 1 1 d . . . H25 H 0.0919 0.2034 0.3415 0.061 Uiso 1 1 calc R . . C27 C 0.2517(13) 0.4153(8) 0.2730(2) 0.0641(19) Uani 1 1 d . . . H27 H 0.2023 0.5111 0.2573 0.077 Uiso 1 1 calc R . . C29 C 0.7492(10) 0.0684(9) 0.2876(2) 0.0553(17) Uani 1 1 d . . . H29 H 0.8406 0.0977 0.2693 0.066 Uiso 1 1 calc R . . C34 C 0.2580(9) 0.0281(6) 0.41055(17) 0.0396(15) Uani 1 1 d . . . C39 C -0.0190(11) 0.1473(8) 0.4603(2) 0.0577(18) Uani 1 1 d . . . H39 H -0.1593 0.1642 0.4696 0.069 Uiso 1 1 calc R . . C38 C 0.1185(12) 0.2112(8) 0.4816(2) 0.0564(18) Uani 1 1 d . . . C35 C 0.0514(10) 0.0584(7) 0.4251(2) 0.0516(17) Uani 1 1 d . . . H35 H -0.0439 0.0173 0.4107 0.062 Uiso 1 1 calc R . . C36 C 0.3929(10) 0.0957(8) 0.4322(2) 0.0585(18) Uani 1 1 d . . . H36 H 0.5319 0.0815 0.4225 0.070 Uiso 1 1 calc R . . C37 C 0.3244(11) 0.1841(8) 0.4678(2) 0.0624(19) Uani 1 1 d . . . H37 H 0.4190 0.2250 0.4825 0.075 Uiso 1 1 calc R . . N2 N 0.4360(8) -0.2527(5) 0.38567(14) 0.0481(13) Uani 1 1 d . . . C40 C 0.6608(11) -0.2936(7) 0.3941(2) 0.0591(18) Uani 1 1 d . . . H40 H 0.6853 -0.2369 0.4188 0.071 Uiso 1 1 calc R . . C41 C 0.7329(12) -0.4785(8) 0.4002(2) 0.077(2) Uani 1 1 d . . . H41A H 0.7231 -0.5061 0.4288 0.093 Uiso 1 1 calc R . . H41B H 0.8804 -0.5277 0.3909 0.093 Uiso 1 1 calc R . . C43 C 0.5773(13) -0.5385(8) 0.3744(3) 0.087(2) Uani 1 1 d . . . H43A H 0.6537 -0.6100 0.3525 0.105 Uiso 1 1 calc R . . H43B H 0.5040 -0.5995 0.3911 0.105 Uiso 1 1 calc R . . C42 C 0.4173(11) -0.3828(8) 0.3573(2) 0.068(2) Uani 1 1 d . . . H42A H 0.4558 -0.3613 0.3297 0.082 Uiso 1 1 calc R . . H42B H 0.2720 -0.3911 0.3574 0.082 Uiso 1 1 calc R . . C44 C 0.3354(9) -0.0794(7) 0.37279(17) 0.0451(16) Uani 1 1 d . . . H44 H 0.2064 -0.0768 0.3572 0.054 Uiso 1 1 calc R . . C45 C -0.1522(12) 0.3511(9) 0.5302(2) 0.083(2) Uani 1 1 d . . . H45A H -0.2406 0.4127 0.5086 0.125 Uiso 1 1 calc R . . H45B H -0.1689 0.4198 0.5541 0.125 Uiso 1 1 calc R . . H45C H -0.1954 0.2552 0.5364 0.125 Uiso 1 1 calc R . . O4 O 0.0677(8) 0.3000(6) 0.51752(15) 0.0763(14) Uani 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 C2 0.049(4) 0.050(4) 0.044(4) 0.000(4) 0.003(3) -0.024(4) C3 0.033(4) 0.047(4) 0.042(4) 0.013(3) -0.002(3) -0.017(3) C1 0.044(4) 0.041(4) 0.043(4) -0.001(3) -0.002(3) -0.018(4) C12 0.048(4) 0.042(4) 0.038(4) 0.011(3) 0.001(3) -0.016(4) C8 0.050(5) 0.056(4) 0.042(4) 0.015(4) -0.007(4) -0.024(4) C10 0.037(4) 0.072(5) 0.067(5) 0.025(4) -0.006(4) -0.022(4) C11 0.046(5) 0.048(4) 0.052(4) 0.012(4) 0.005(4) -0.018(4) C7 0.065(5) 0.060(5) 0.053(4) -0.003(4) -0.007(4) -0.034(4) C5 0.055(4) 0.064(5) 0.063(5) -0.001(4) 0.000(4) -0.020(4) C4 0.059(5) 0.055(4) 0.047(4) -0.004(4) 0.001(3) -0.030(4) C6 0.081(6) 0.054(4) 0.064(5) -0.010(4) 0.005(4) -0.026(5) C9 0.060(5) 0.068(5) 0.055(5) 0.014(4) -0.006(4) -0.042(4) C13 0.046(4) 0.042(4) 0.048(4) 0.000(3) 0.006(3) -0.018(3) C14 0.048(4) 0.036(3) 0.044(4) 0.001(3) 0.003(3) -0.021(3) C17 0.062(5) 0.047(4) 0.046(5) 0.009(4) -0.005(4) -0.013(4) C19 0.058(4) 0.061(4) 0.059(5) 0.004(4) -0.013(4) -0.024(4) C18 0.049(4) 0.058(4) 0.055(5) 0.005(4) 0.000(4) -0.031(3) C15 0.054(4) 0.057(4) 0.067(5) 0.016(4) -0.007(4) -0.025(4) C16 0.060(5) 0.061(4) 0.070(5) 0.025(4) -0.001(4) -0.025(4) C20 0.070(5) 0.045(4) 0.056(5) 0.005(3) 0.007(4) -0.013(4) C21 0.122(7) 0.040(4) 0.072(5) 0.006(4) 0.006(5) -0.004(4) C22 0.091(5) 0.044(4) 0.075(5) 0.013(4) -0.001(4) -0.031(4) C23 0.116(6) 0.051(5) 0.103(6) 0.014(5) -0.011(5) -0.036(5) C24 0.111(7) 0.069(5) 0.074(5) 0.014(4) -0.034(5) -0.026(5) O1 0.062(3) 0.055(3) 0.076(3) 0.003(3) 0.007(3) -0.011(2) O2 0.087(4) 0.082(3) 0.061(3) 0.024(3) -0.013(3) -0.025(3) N1 0.065(4) 0.035(3) 0.051(3) 0.007(3) 0.004(3) -0.017(3) O3 0.064(3) 0.054(3) 0.075(3) 0.007(3) -0.005(3) -0.011(3) C32 0.047(4) 0.037(4) 0.037(4) 0.001(3) -0.002(3) -0.016(3) C30 0.040(4) 0.071(5) 0.066(5) -0.019(4) 0.006(4) -0.023(4) C28 0.065(5) 0.064(5) 0.058(5) 0.014(4) 0.002(4) -0.034(4) C31 0.049(5) 0.046(4) 0.053(4) -0.005(4) -0.005(4) -0.019(4) C26 0.061(4) 0.056(5) 0.069(5) 0.016(4) -0.002(4) -0.017(4) C25 0.065(5) 0.051(4) 0.044(4) 0.012(3) -0.001(3) -0.030(4) C27 0.081(6) 0.053(4) 0.062(5) 0.026(4) -0.013(4) -0.024(5) C29 0.054(5) 0.063(5) 0.058(5) -0.006(4) 0.010(4) -0.031(4) C34 0.043(4) 0.037(3) 0.046(4) 0.008(3) -0.004(3) -0.021(3) C39 0.056(4) 0.055(4) 0.063(5) 0.001(4) 0.015(4) -0.018(4) C38 0.071(5) 0.046(4) 0.048(5) 0.001(4) 0.009(4) -0.012(4) C35 0.044(4) 0.054(4) 0.065(5) 0.003(4) 0.004(4) -0.028(3) C36 0.055(4) 0.062(4) 0.064(5) -0.009(4) 0.012(4) -0.028(4) C37 0.058(5) 0.065(5) 0.067(5) -0.015(4) 0.004(4) -0.023(4) N2 0.060(4) 0.035(3) 0.051(3) 0.001(3) -0.005(3) -0.017(3) C40 0.075(5) 0.047(5) 0.054(5) 0.007(3) -0.015(4) -0.016(4) C41 0.105(6) 0.046(5) 0.073(5) 0.003(4) -0.008(4) -0.010(4) C43 0.111(6) 0.041(4) 0.110(7) 0.003(4) 0.008(5) -0.023(5) C42 0.091(5) 0.054(5) 0.072(5) -0.007(4) 0.007(4) -0.041(4) C44 0.052(4) 0.041(4) 0.048(4) 0.007(3) -0.008(3) -0.022(3) C45 0.096(6) 0.075(5) 0.077(5) -0.004(4) 0.025(5) -0.022(5) O4 0.077(4) 0.081(3) 0.068(3) -0.016(3) 0.012(3) -0.021(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 C2 C29 1.396(8) . ? C2 C28 1.403(8) . ? C2 C1 1.417(8) . ? C3 C8 1.400(8) . ? C3 C4 1.412(7) . ? C3 C12 1.441(8) . ? C1 C25 1.408(7) . ? C1 C32 1.433(8) . ? C12 C11 1.358(8) . ? C12 C13 1.511(8) . ? C8 C9 1.400(8) . ? C8 C7 1.418(8) . ? C10 C9 1.360(8) . ? C10 C11 1.418(8) . ? C11 O1 1.381(7) . ? C7 C6 1.353(8) . ? C5 C4 1.378(8) . ? C5 C6 1.392(9) . ? C13 N1 1.473(7) . ? C13 C14 1.524(8) . ? C14 C18 1.373(7) . ? C14 C15 1.381(8) . ? C17 C16 1.359(8) . ? C17 O2 1.377(7) . ? C17 C19 1.379(8) . ? C19 C18 1.382(8) . ? C15 C16 1.392(8) . ? C20 N1 1.419(7) . ? C20 O1 1.462(7) . ? C20 C21 1.514(8) . ? C21 C23 1.517(10) . ? C22 N1 1.475(7) . ? C22 C23 1.521(9) . ? C24 O2 1.412(7) . ? O3 C31 1.380(7) . ? O3 C40 1.457(7) . ? C32 C31 1.353(7) . ? C32 C44 1.514(8) . ? C30 C29 1.357(8) . ? C30 C31 1.414(8) . ? C28 C27 1.348(8) . ? C26 C25 1.370(8) . ? C26 C27 1.404(9) . ? C34 C35 1.373(7) . ? C34 C36 1.385(8) . ? C34 C44 1.525(7) . ? C39 C35 1.374(8) . ? C39 C38 1.375(9) . ? C38 C37 1.364(8) . ? C38 O4 1.378(7) . ? C36 C37 1.383(8) . ? N2 C40 1.426(7) . ? N2 C44 1.475(7) . ? N2 C42 1.475(7) . ? C40 C41 1.505(8) . ? C41 C43 1.525(9) . ? C43 C42 1.517(9) . ? C45 O4 1.423(7) . ? 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 C29 C2 C28 121.4(6) . . ? C29 C2 C1 118.7(6) . . ? C28 C2 C1 119.9(6) . . ? C8 C3 C4 117.6(6) . . ? C8 C3 C12 121.0(5) . . ? C4 C3 C12 121.4(6) . . ? C25 C1 C2 116.9(5) . . ? C25 C1 C32 123.2(5) . . ? C2 C1 C32 119.9(5) . . ? C11 C12 C3 117.0(5) . . ? C11 C12 C13 121.5(6) . . ? C3 C12 C13 121.4(5) . . ? C9 C8 C3 118.8(6) . . ? C9 C8 C7 120.7(6) . . ? C3 C8 C7 120.6(6) . . ? C9 C10 C11 119.2(6) . . ? C12 C11 O1 122.8(6) . . ? C12 C11 C10 122.8(6) . . ? O1 C11 C10 114.4(6) . . ? C6 C7 C8 120.1(6) . . ? C4 C5 C6 120.6(6) . . ? C5 C4 C3 120.8(6) . . ? C7 C6 C5 120.3(6) . . ? C10 C9 C8 121.3(6) . . ? N1 C13 C12 110.9(5) . . ? N1 C13 C14 109.0(4) . . ? C12 C13 C14 115.6(5) . . ? C18 C14 C15 117.1(5) . . ? C18 C14 C13 120.5(5) . . ? C15 C14 C13 122.4(5) . . ? C16 C17 O2 116.2(6) . . ? C16 C17 C19 119.3(6) . . ? O2 C17 C19 124.5(6) . . ? C17 C19 C18 118.9(6) . . ? C14 C18 C19 123.0(6) . . ? C14 C15 C16 120.5(6) . . ? C17 C16 C15 121.1(6) . . ? N1 C20 O1 113.7(5) . . ? N1 C20 C21 104.4(6) . . ? O1 C20 C21 106.6(5) . . ? C20 C21 C23 103.9(6) . . ? N1 C22 C23 103.0(5) . . ? C21 C23 C22 105.7(5) . . ? C11 O1 C20 115.3(5) . . ? C17 O2 C24 118.6(5) . . ? C20 N1 C13 114.2(4) . . ? C20 N1 C22 104.9(5) . . ? C13 N1 C22 116.4(5) . . ? C31 O3 C40 115.5(5) . . ? C31 C32 C1 118.5(5) . . ? C31 C32 C44 120.5(5) . . ? C1 C32 C44 120.9(5) . . ? C29 C30 C31 119.9(6) . . ? C27 C28 C2 121.6(6) . . ? C32 C31 O3 123.5(6) . . ? C32 C31 C30 121.7(6) . . ? O3 C31 C30 114.7(6) . . ? C25 C26 C27 119.8(6) . . ? C26 C25 C1 122.1(6) . . ? C28 C27 C26 119.7(6) . . ? C30 C29 C2 121.2(6) . . ? C35 C34 C36 117.2(6) . . ? C35 C34 C44 120.9(5) . . ? C36 C34 C44 121.9(5) . . ? C35 C39 C38 119.8(6) . . ? C37 C38 C39 119.5(6) . . ? C37 C38 O4 115.3(7) . . ? C39 C38 O4 125.1(6) . . ? C34 C35 C39 122.1(6) . . ? C34 C36 C37 121.1(6) . . ? C38 C37 C36 120.2(6) . . ? C40 N2 C44 114.0(4) . . ? C40 N2 C42 105.0(5) . . ? C44 N2 C42 116.7(5) . . ? N2 C40 O3 113.0(5) . . ? N2 C40 C41 104.3(5) . . ? O3 C40 C41 106.7(5) . . ? C40 C41 C43 104.3(5) . . ? C42 C43 C41 105.4(5) . . ? N2 C42 C43 102.9(5) . . ? N2 C44 C32 111.3(5) . . ? N2 C44 C34 109.1(4) . . ? C32 C44 C34 115.7(4) . . ? C38 O4 C45 117.4(6) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 19.90 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.243 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 952462' ####################################################################### # # 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_mono _audit_creation_method SHELXL-97 _chemical_name_systematic rac-(7aS,11S)-11-Pyridine-2-yl-7a,8,9,10-tetrahydro-11H-7-oxa-10a-aza-cyclopenta[b]phenanthrene _chemical_name_common ? _chemical_formula_moiety 'C20 H18 N2 O' _chemical_formula_sum 'C20 H18 N2 O' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 296(2) _chemical_formula_weight 302.36 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 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5276(5) _cell_length_b 8.3530(4) _cell_length_c 18.0400(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.988(3) _cell_angle_gamma 90.00 _cell_volume 1551.79(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15036 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.23 _reflns_number_total 3446 _reflns_number_gt 1693 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0575P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3446 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1305 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C7 C 0.22594(16) 0.6604(2) -0.01533(9) 0.0406(5) Uani 1 1 d . . . C8 C 0.25694(17) 0.5194(2) -0.04677(10) 0.0474(5) Uani 1 1 d . . . C6 C 0.17849(16) 0.7899(2) -0.06493(10) 0.0446(5) Uani 1 1 d . . . C5 C 0.16433(17) 0.7713(3) -0.14451(10) 0.0526(5) Uani 1 1 d . . . C1 C 0.14476(17) 0.9401(2) -0.03763(11) 0.0508(5) Uani 1 1 d . . . H1 H 0.1521 0.9550 0.0142 0.061 Uiso 1 1 calc R . . C10 C 0.19668(19) 0.6222(3) -0.17290(11) 0.0627(6) Uani 1 1 d . . . H10 H 0.1871 0.6081 -0.2249 0.075 Uiso 1 1 calc R . . C9 C 0.24139(18) 0.5001(3) -0.12542(11) 0.0602(6) Uani 1 1 d . . . H9 H 0.2619 0.4027 -0.1450 0.072 Uiso 1 1 calc R . . C4 C 0.1183(2) 0.9017(3) -0.19252(12) 0.0710(7) Uani 1 1 d . . . H4 H 0.1087 0.8898 -0.2447 0.085 Uiso 1 1 calc R . . C2 C 0.10181(18) 1.0629(3) -0.08626(14) 0.0651(6) Uani 1 1 d . . . H2 H 0.0815 1.1608 -0.0671 0.078 Uiso 1 1 calc R . . C3 C 0.0879(2) 1.0436(3) -0.16434(15) 0.0748(7) Uani 1 1 d . . . H3 H 0.0578 1.1280 -0.1969 0.090 Uiso 1 1 calc R . . O1 O 0.30310(13) 0.38724(15) -0.00462(7) 0.0617(4) Uani 1 1 d . . . N1 N 0.25341(14) 0.51485(18) 0.10527(8) 0.0461(4) Uani 1 1 d . . . C15 C 0.23980(16) 0.6732(2) 0.06941(9) 0.0419(5) Uani 1 1 d . . . H15 H 0.1597 0.7210 0.0789 0.050 Uiso 1 1 calc R . . C11 C 0.33916(19) 0.4110(2) 0.07734(11) 0.0546(6) Uani 1 1 d . . . H11 H 0.4291 0.4483 0.0924 0.065 Uiso 1 1 calc R . . C12 C 0.3222(2) 0.2505(2) 0.11305(12) 0.0694(7) Uani 1 1 d . . . H12A H 0.3885 0.2344 0.1585 0.083 Uiso 1 1 calc R . . H12B H 0.3269 0.1639 0.0779 0.083 Uiso 1 1 calc R . . C14 C 0.13479(19) 0.4208(2) 0.10292(11) 0.0590(6) Uani 1 1 d . . . H14A H 0.0837 0.4133 0.0517 0.071 Uiso 1 1 calc R . . H14B H 0.0818 0.4669 0.1355 0.071 Uiso 1 1 calc R . . C13 C 0.1880(2) 0.2589(3) 0.13187(13) 0.0776(7) Uani 1 1 d . . . H13A H 0.1330 0.1734 0.1068 0.093 Uiso 1 1 calc R . . H13B H 0.1938 0.2504 0.1861 0.093 Uiso 1 1 calc R . . C16 C 0.35252(17) 0.7773(2) 0.10904(10) 0.0400(5) Uani 1 1 d . . . C17 C 0.45825(18) 0.8109(2) 0.07839(11) 0.0534(5) Uani 1 1 d . . . H17 H 0.4616 0.7756 0.0299 0.064 Uiso 1 1 calc R . . C20 C 0.4420(2) 0.9135(2) 0.21661(11) 0.0578(6) Uani 1 1 d . . . H20 H 0.4363 0.9502 0.2645 0.069 Uiso 1 1 calc R . . C18 C 0.56012(19) 0.8980(2) 0.12056(12) 0.0627(6) Uani 1 1 d . . . H18 H 0.6331 0.9211 0.1010 0.075 Uiso 1 1 calc R . . C19 C 0.5520(2) 0.9493(2) 0.19109(12) 0.0593(6) Uani 1 1 d . . . H19 H 0.6193 1.0069 0.2209 0.071 Uiso 1 1 calc R . . N2 N 0.34202(14) 0.82950(18) 0.17778(8) 0.0500(4) Uani 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 C7 0.0329(10) 0.0506(12) 0.0387(11) 0.0001(9) 0.0087(8) 0.0000(9) C8 0.0413(11) 0.0572(13) 0.0452(12) -0.0033(10) 0.0122(9) -0.0004(10) C6 0.0306(10) 0.0565(13) 0.0464(12) 0.0028(10) 0.0074(8) -0.0054(9) C5 0.0396(12) 0.0755(15) 0.0421(12) 0.0065(11) 0.0070(9) -0.0107(11) C1 0.0391(11) 0.0560(13) 0.0566(12) 0.0074(11) 0.0086(9) -0.0022(10) C10 0.0561(14) 0.0937(18) 0.0399(12) -0.0051(12) 0.0135(10) -0.0085(13) C9 0.0618(14) 0.0729(15) 0.0500(13) -0.0154(12) 0.0209(10) -0.0016(12) C4 0.0561(14) 0.097(2) 0.0542(14) 0.0236(14) -0.0010(11) -0.0186(14) C2 0.0449(13) 0.0632(15) 0.0845(17) 0.0150(13) 0.0076(12) -0.0013(11) C3 0.0517(15) 0.0793(19) 0.0849(19) 0.0375(15) -0.0056(13) -0.0056(13) O1 0.0710(10) 0.0561(9) 0.0603(9) -0.0014(7) 0.0191(7) 0.0132(7) N1 0.0464(10) 0.0449(9) 0.0463(9) 0.0030(7) 0.0081(7) -0.0061(8) C15 0.0385(11) 0.0478(11) 0.0404(11) 0.0003(9) 0.0106(8) 0.0023(9) C11 0.0484(12) 0.0524(13) 0.0578(13) 0.0000(10) -0.0005(10) 0.0010(11) C12 0.0792(17) 0.0462(13) 0.0727(15) 0.0048(11) -0.0073(12) -0.0021(12) C14 0.0601(13) 0.0610(14) 0.0587(13) -0.0045(11) 0.0189(10) -0.0175(12) C13 0.0955(19) 0.0594(16) 0.0803(16) 0.0043(12) 0.0238(14) -0.0152(13) C16 0.0396(11) 0.0398(11) 0.0407(11) 0.0028(8) 0.0081(9) 0.0020(9) C17 0.0440(12) 0.0654(13) 0.0529(12) -0.0071(10) 0.0150(10) -0.0030(11) C20 0.0608(14) 0.0625(14) 0.0476(12) -0.0062(10) 0.0056(11) -0.0038(12) C18 0.0434(12) 0.0734(15) 0.0729(16) -0.0037(12) 0.0158(11) -0.0086(11) C19 0.0469(13) 0.0619(14) 0.0625(14) -0.0047(11) -0.0038(11) -0.0048(11) N2 0.0534(10) 0.0576(10) 0.0394(9) -0.0059(8) 0.0109(8) -0.0060(9) _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 C7 C8 1.375(2) . ? C7 C6 1.427(2) . ? C7 C15 1.509(2) . ? C8 O1 1.371(2) . ? C8 C9 1.403(2) . ? C6 C1 1.419(2) . ? C6 C5 1.421(2) . ? C5 C4 1.413(3) . ? C5 C10 1.415(3) . ? C1 C2 1.364(2) . ? C10 C9 1.352(3) . ? C4 C3 1.354(3) . ? C2 C3 1.395(3) . ? O1 C11 1.462(2) . ? N1 C11 1.418(2) . ? N1 C15 1.466(2) . ? N1 C14 1.468(2) . ? C15 C16 1.524(2) . ? C11 C12 1.513(2) . ? C12 C13 1.522(3) . ? C14 C13 1.515(3) . ? C16 N2 1.341(2) . ? C16 C17 1.371(2) . ? C17 C18 1.385(2) . ? C20 N2 1.336(2) . ? C20 C19 1.365(3) . ? C18 C19 1.362(3) . ? 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 C8 C7 C6 118.22(17) . . ? C8 C7 C15 119.81(16) . . ? C6 C7 C15 121.95(17) . . ? O1 C8 C7 123.22(16) . . ? O1 C8 C9 114.94(17) . . ? C7 C8 C9 121.83(18) . . ? C1 C6 C5 117.76(17) . . ? C1 C6 C7 122.20(17) . . ? C5 C6 C7 120.04(18) . . ? C4 C5 C10 122.3(2) . . ? C4 C5 C6 119.1(2) . . ? C10 C5 C6 118.63(18) . . ? C2 C1 C6 120.98(19) . . ? C9 C10 C5 120.88(19) . . ? C10 C9 C8 120.38(19) . . ? C3 C4 C5 121.5(2) . . ? C1 C2 C3 120.9(2) . . ? C4 C3 C2 119.8(2) . . ? C8 O1 C11 116.08(14) . . ? C11 N1 C15 113.98(15) . . ? C11 N1 C14 105.22(15) . . ? C15 N1 C14 117.72(14) . . ? N1 C15 C7 111.29(14) . . ? N1 C15 C16 108.22(13) . . ? C7 C15 C16 114.68(15) . . ? N1 C11 O1 113.05(14) . . ? N1 C11 C12 104.51(18) . . ? O1 C11 C12 106.36(15) . . ? C11 C12 C13 104.57(17) . . ? N1 C14 C13 102.51(16) . . ? C14 C13 C12 104.93(17) . . ? N2 C16 C17 122.46(16) . . ? N2 C16 C15 114.43(16) . . ? C17 C16 C15 123.07(16) . . ? C16 C17 C18 119.12(18) . . ? N2 C20 C19 124.72(19) . . ? C19 C18 C17 119.1(2) . . ? C18 C19 C20 117.91(18) . . ? C20 N2 C16 116.63(17) . . ? _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.900 _refine_diff_density_max 0.133 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 952463' ####################################################################### # # 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_shhhhh _audit_creation_method SHELXL-97 _chemical_name_systematic rac-(1R,3S)-2-ethyl-3-methyl-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine _chemical_name_common ? _chemical_formula_moiety 'C21 H21 N O' _chemical_formula_sum 'C21 H21 N O' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colorless _diffrn_ambient_temperature 296(2) _chemical_formula_weight 303.39 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.4433(3) _cell_length_b 11.6711(4) _cell_length_c 17.1926(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.061(2) _cell_angle_gamma 90.00 _cell_volume 1689.95(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19899 _diffrn_reflns_av_R_equivalents 0.1741 _diffrn_reflns_av_sigmaI/netI 0.1151 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2964 _reflns_number_gt 1258 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2964 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1216 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.0732 _refine_ls_wR_factor_gt 0.0644 _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_restrained_S_all 0.890 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C7 C 0.2753(3) 0.14081(18) 0.32052(13) 0.0448(7) Uani 1 1 d . . . C1 C 0.1413(3) 0.3245(2) 0.34228(16) 0.0553(7) Uani 1 1 d . . . C8 C 0.2183(3) 0.1457(2) 0.24372(15) 0.0542(7) Uani 1 1 d . . . C6 C 0.2360(3) 0.23179(19) 0.37109(14) 0.0479(7) Uani 1 1 d . . . C5 C 0.2925(3) 0.23491(18) 0.45033(13) 0.0562(7) Uani 1 1 d . . . H5 H 0.3522 0.1739 0.4712 0.067 Uiso 1 1 calc R . . C2 C 0.1114(3) 0.4171(2) 0.39205(17) 0.0732(9) Uani 1 1 d . . . H2 H 0.0503 0.4785 0.3728 0.088 Uiso 1 1 calc R . . C9 C 0.1216(3) 0.2363(2) 0.21457(13) 0.0696(8) Uani 1 1 d . . . H9 H 0.0839 0.2371 0.1624 0.083 Uiso 1 1 calc R . . C4 C 0.2612(3) 0.3259(2) 0.49690(13) 0.0686(8) Uani 1 1 d . . . H4 H 0.3008 0.3265 0.5488 0.082 Uiso 1 1 calc R . . C10 C 0.0834(3) 0.32293(19) 0.26303(17) 0.0696(8) Uani 1 1 d . . . H10 H 0.0181 0.3820 0.2436 0.084 Uiso 1 1 calc R . . C3 C 0.1703(4) 0.4177(2) 0.46724(17) 0.0784(10) Uani 1 1 d . . . H3 H 0.1501 0.4795 0.4992 0.094 Uiso 1 1 calc R . . O1 O 0.2562(2) 0.06631(14) 0.18857(7) 0.0686(5) Uani 1 1 d . . . C17 C 0.3858(3) 0.04398(17) 0.34629(11) 0.0476(6) Uani 1 1 d . . . H17 H 0.4677 0.0766 0.3830 0.057 Uiso 1 1 calc R . . C12 C 0.3075(3) -0.0533(2) 0.38873(11) 0.0491(7) Uani 1 1 d . . . C11 C 0.1569(3) -0.04400(19) 0.41404(12) 0.0586(8) Uani 1 1 d . . . H11 H 0.0990 0.0228 0.4038 0.070 Uiso 1 1 calc R . . C14 C 0.3211(4) -0.2440(2) 0.44273(14) 0.0840(10) Uani 1 1 d . . . H14 H 0.3772 -0.3119 0.4517 0.101 Uiso 1 1 calc R . . C15 C 0.1716(4) -0.2320(2) 0.46866(14) 0.0761(9) Uani 1 1 d . . . H15 H 0.1265 -0.2914 0.4956 0.091 Uiso 1 1 calc R . . C13 C 0.3879(3) -0.1548(2) 0.40311(12) 0.0705(8) Uani 1 1 d . . . H13 H 0.4892 -0.1635 0.3859 0.085 Uiso 1 1 calc R . . C16 C 0.0900(3) -0.1324(2) 0.45457(12) 0.0684(8) Uani 1 1 d . . . H16 H -0.0109 -0.1237 0.4722 0.082 Uiso 1 1 calc R . . N2 N 0.4680(3) -0.00195(14) 0.27966(10) 0.0531(6) Uani 1 1 d . . . C18 C 0.3496(3) -0.03177(18) 0.21941(14) 0.0599(7) Uani 1 1 d . . . H18 H 0.2758 -0.0850 0.2421 0.072 Uiso 1 1 calc R . . C19 C 0.5945(3) 0.0748(2) 0.25489(13) 0.0735(8) Uani 1 1 d . . . H19A H 0.5506 0.1507 0.2452 0.088 Uiso 1 1 calc R . . H19B H 0.6321 0.0466 0.2064 0.088 Uiso 1 1 calc R . . C20 C 0.7337(3) 0.08318(19) 0.31554(14) 0.1010(10) Uani 1 1 d . . . H20A H 0.7027 0.1262 0.3595 0.151 Uiso 1 1 calc R . . H20B H 0.8208 0.1210 0.2933 0.151 Uiso 1 1 calc R . . H20C H 0.7657 0.0076 0.3322 0.151 Uiso 1 1 calc R . . C21 C 0.4100(3) -0.08985(16) 0.14806(11) 0.0851(9) Uani 1 1 d . . . H21A H 0.4628 -0.0345 0.1177 0.128 Uiso 1 1 calc R . . H21B H 0.3221 -0.1222 0.1170 0.128 Uiso 1 1 calc R . . H21C H 0.4832 -0.1495 0.1644 0.128 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 C7 0.0523(19) 0.0428(15) 0.0398(15) 0.0068(13) 0.0072(13) 0.0055(13) C1 0.058(2) 0.0516(18) 0.0583(19) 0.0074(16) 0.0165(16) 0.0022(15) C8 0.061(2) 0.0547(18) 0.0475(17) 0.0041(15) 0.0088(15) 0.0059(15) C6 0.055(2) 0.0408(16) 0.0494(17) 0.0052(14) 0.0144(15) 0.0021(14) C5 0.062(2) 0.0556(17) 0.0527(17) -0.0060(14) 0.0135(15) 0.0012(14) C2 0.071(2) 0.0532(18) 0.099(2) 0.0008(19) 0.027(2) 0.0113(16) C9 0.074(2) 0.079(2) 0.0557(18) 0.0156(16) 0.0042(16) 0.0112(18) C4 0.076(2) 0.0661(19) 0.0660(19) -0.0172(16) 0.0200(17) -0.0028(17) C10 0.065(2) 0.0622(19) 0.083(2) 0.0200(16) 0.0143(18) 0.0220(16) C3 0.080(3) 0.064(2) 0.094(2) -0.021(2) 0.031(2) 0.0056(18) O1 0.0834(16) 0.0766(12) 0.0451(10) -0.0052(9) 0.0004(10) 0.0209(11) C17 0.0518(19) 0.0486(15) 0.0428(14) -0.0044(12) 0.0067(13) 0.0002(14) C12 0.058(2) 0.0475(17) 0.0425(15) 0.0031(12) 0.0056(14) 0.0034(16) C11 0.071(2) 0.0477(16) 0.0587(17) -0.0009(13) 0.0173(16) 0.0035(16) C14 0.084(3) 0.066(2) 0.102(2) 0.0290(16) 0.005(2) 0.008(2) C15 0.094(3) 0.071(2) 0.0630(18) 0.0129(16) 0.0010(18) -0.014(2) C13 0.065(2) 0.0669(19) 0.0803(18) 0.0232(15) 0.0091(16) 0.0108(18) C16 0.079(2) 0.0688(19) 0.0597(17) -0.0061(16) 0.0218(16) -0.0107(18) N2 0.0558(16) 0.0568(14) 0.0480(13) -0.0038(11) 0.0116(12) 0.0008(12) C18 0.072(2) 0.0583(18) 0.0501(17) -0.0061(14) 0.0111(15) 0.0006(16) C19 0.067(2) 0.0774(19) 0.080(2) -0.0047(16) 0.0310(18) -0.0034(18) C20 0.062(2) 0.116(2) 0.127(2) -0.0184(19) 0.018(2) -0.013(2) C21 0.113(3) 0.0858(18) 0.0582(16) -0.0215(14) 0.0206(17) 0.0133(18) _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 C7 C8 1.374(2) . ? C7 C6 1.426(2) . ? C7 C17 1.512(2) . ? C1 C2 1.412(3) . ? C1 C6 1.414(3) . ? C1 C10 1.415(3) . ? C8 O1 1.379(2) . ? C8 C9 1.406(3) . ? C6 C5 1.412(2) . ? C5 C4 1.367(2) . ? C2 C3 1.352(3) . ? C9 C10 1.363(2) . ? C4 C3 1.393(3) . ? O1 C18 1.468(2) . ? C17 N2 1.481(2) . ? C17 C12 1.526(2) . ? C12 C11 1.377(3) . ? C12 C13 1.378(3) . ? C11 C16 1.387(2) . ? C14 C15 1.375(3) . ? C14 C13 1.386(3) . ? C15 C16 1.364(3) . ? N2 C18 1.431(3) . ? N2 C19 1.480(2) . ? C18 C21 1.521(2) . ? C19 C20 1.518(3) . ? 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 C8 C7 C6 118.3(2) . . ? C8 C7 C17 118.6(2) . . ? C6 C7 C17 122.9(2) . . ? C2 C1 C6 119.6(3) . . ? C2 C1 C10 122.0(3) . . ? C6 C1 C10 118.4(2) . . ? C7 C8 O1 123.4(2) . . ? C7 C8 C9 121.9(2) . . ? O1 C8 C9 114.6(2) . . ? C5 C6 C1 117.5(2) . . ? C5 C6 C7 122.0(2) . . ? C1 C6 C7 120.4(2) . . ? C4 C5 C6 121.3(2) . . ? C3 C2 C1 121.0(3) . . ? C10 C9 C8 119.8(2) . . ? C5 C4 C3 120.5(2) . . ? C9 C10 C1 121.2(2) . . ? C2 C3 C4 120.1(3) . . ? C8 O1 C18 114.85(17) . . ? N2 C17 C7 110.94(17) . . ? N2 C17 C12 110.07(17) . . ? C7 C17 C12 114.6(2) . . ? C11 C12 C13 117.7(2) . . ? C11 C12 C17 122.2(2) . . ? C13 C12 C17 120.0(2) . . ? C12 C11 C16 121.2(2) . . ? C15 C14 C13 119.8(3) . . ? C16 C15 C14 119.5(3) . . ? C12 C13 C14 121.4(3) . . ? C15 C16 C11 120.3(3) . . ? C18 N2 C19 114.88(18) . . ? C18 N2 C17 107.8(2) . . ? C19 N2 C17 112.99(17) . . ? N2 C18 O1 113.71(17) . . ? N2 C18 C21 115.8(2) . . ? O1 C18 C21 104.99(19) . . ? N2 C19 C20 112.4(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.125 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 952464' ####################################################################### # # 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_sh _audit_creation_method SHELXL-97 _chemical_name_systematic rac-(7aS,12R)-12-(3-Nitro-phenyl)-8,9,10,11-tetrahydro-7aH,12H-7-oxa-11a-aza-benzo[a]anthracene _chemical_name_common ? _chemical_formula_moiety 'C22 H20 N2 O3' _chemical_formula_sum 'C22 H20 N2 O3' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 296(2) _chemical_formula_weight 360.40 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 'P c a 21' _symmetry_int_tables_number 29 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 8.8679(18) _cell_length_b 15.764(3) _cell_length_c 13.088(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1829.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19032 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.59 _reflns_number_total 3926 _reflns_number_gt 2632 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0492P)^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 mixed _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 0.4(14) _refine_ls_number_reflns 3926 _refine_ls_number_parameters 244 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0825 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.010 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.17976(17) 0.27288(11) 0.68205(12) 0.0502(5) Uani 1 1 d . . . N1 N 0.11732(18) 0.21884(12) 0.51322(14) 0.0376(5) Uani 1 1 d . . . C2 C 0.4634(2) 0.35933(14) 0.50198(18) 0.0378(5) Uani 1 1 d . . . C6 C 0.2964(2) 0.31740(15) 0.63977(17) 0.0416(6) Uani 1 1 d . . . C1 C 0.3443(2) 0.30691(14) 0.54008(16) 0.0356(5) Uani 1 1 d . . . C3 C 0.5329(2) 0.41959(15) 0.5685(2) 0.0440(6) Uani 1 1 d . . . C5 C 0.3649(3) 0.37779(16) 0.7051(2) 0.0498(6) Uani 1 1 d . . . H5 H 0.3304 0.3843 0.7717 0.060 Uiso 1 1 calc R . . C10 C 0.2687(2) 0.24108(13) 0.47286(17) 0.0366(5) Uani 1 1 d . . . H10 H 0.2552 0.2660 0.4049 0.044 Uiso 1 1 calc R . . C4 C 0.4802(3) 0.42591(17) 0.6708(2) 0.0513(7) Uani 1 1 d . . . H4 H 0.5263 0.4641 0.7151 0.062 Uiso 1 1 calc R . . C8 C 0.1238(2) 0.20063(16) 0.62071(18) 0.0433(6) Uani 1 1 d . . . H8 H 0.1931 0.1529 0.6306 0.052 Uiso 1 1 calc R . . C11 C 0.5149(2) 0.35532(16) 0.3994(2) 0.0447(6) Uani 1 1 d . . . H11 H 0.4709 0.3169 0.3545 0.054 Uiso 1 1 calc R . . C12 C 0.6286(3) 0.40721(17) 0.3655(2) 0.0550(7) Uani 1 1 d . . . H12 H 0.6599 0.4040 0.2978 0.066 Uiso 1 1 calc R . . C13 C 0.6977(3) 0.46482(18) 0.4318(2) 0.0633(8) Uani 1 1 d . . . H13 H 0.7762 0.4988 0.4085 0.076 Uiso 1 1 calc R . . C14 C 0.6504(3) 0.47122(16) 0.5305(2) 0.0578(8) Uani 1 1 d . . . H14 H 0.6962 0.5103 0.5737 0.069 Uiso 1 1 calc R . . C15 C 0.3579(2) 0.15912(14) 0.46054(18) 0.0365(5) Uani 1 1 d . . . C20 C 0.3827(2) 0.02558(16) 0.3757(2) 0.0450(6) Uani 1 1 d . . . C19 C 0.4710(2) 0.13424(16) 0.52699(19) 0.0478(6) Uani 1 1 d . . . H19 H 0.5025 0.1711 0.5782 0.057 Uiso 1 1 calc R . . C16 C 0.3154(2) 0.10394(16) 0.38209(18) 0.0416(6) Uani 1 1 d . . . H16 H 0.2425 0.1200 0.3348 0.050 Uiso 1 1 calc R . . C18 C 0.5381(3) 0.05485(17) 0.5182(2) 0.0596(8) Uani 1 1 d . . . H18 H 0.6143 0.0392 0.5632 0.071 Uiso 1 1 calc R . . C17 C 0.4921(3) -0.00078(19) 0.4431(2) 0.0562(7) Uani 1 1 d . . . H17 H 0.5340 -0.0547 0.4381 0.067 Uiso 1 1 calc R . . N2 N 0.3374(3) -0.03178(19) 0.2922(2) 0.0682(7) Uani 1 1 d . . . O3 O 0.2437(3) -0.00611(14) 0.23028(18) 0.0858(7) Uani 1 1 d . . . O2 O 0.3955(3) -0.10157(17) 0.2872(2) 0.1083(9) Uani 1 1 d . . . C21 C 0.0000(2) 0.27999(16) 0.4838(2) 0.0510(7) Uani 1 1 d . . . H21A H -0.0024 0.2856 0.4101 0.061 Uiso 1 1 calc R . . H21B H 0.0231 0.3351 0.5128 0.061 Uiso 1 1 calc R . . C24 C -0.0265(2) 0.17630(18) 0.6656(2) 0.0521(7) Uani 1 1 d . . . H24A H -0.0178 0.1735 0.7394 0.062 Uiso 1 1 calc R . . H24B H -0.0545 0.1204 0.6412 0.062 Uiso 1 1 calc R . . C23 C -0.1490(3) 0.23922(18) 0.6373(2) 0.0598(8) Uani 1 1 d . . . H23A H -0.1293 0.2933 0.6699 0.072 Uiso 1 1 calc R . . H23B H -0.2460 0.2187 0.6610 0.072 Uiso 1 1 calc R . . C22 C -0.1525(2) 0.25050(19) 0.5219(2) 0.0602(8) Uani 1 1 d . . . H22A H -0.1785 0.1971 0.4896 0.072 Uiso 1 1 calc R . . H22B H -0.2288 0.2919 0.5037 0.072 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 0.0504(9) 0.0580(12) 0.0423(9) -0.0037(9) 0.0041(8) -0.0095(8) N1 0.0335(9) 0.0360(11) 0.0434(11) 0.0040(10) -0.0037(8) -0.0005(8) C2 0.0350(11) 0.0312(13) 0.0472(14) 0.0016(12) -0.0092(10) 0.0005(10) C6 0.0401(12) 0.0407(15) 0.0440(14) -0.0009(12) -0.0069(11) 0.0018(10) C1 0.0364(10) 0.0321(13) 0.0383(13) -0.0006(11) -0.0061(9) 0.0009(9) C3 0.0460(13) 0.0334(14) 0.0524(16) -0.0029(12) -0.0125(12) 0.0009(11) C5 0.0565(14) 0.0505(16) 0.0425(15) -0.0064(13) -0.0080(12) 0.0034(13) C10 0.0360(11) 0.0379(13) 0.0358(12) 0.0012(11) -0.0034(9) -0.0054(10) C4 0.0522(14) 0.0457(17) 0.0560(17) -0.0101(14) -0.0139(13) -0.0023(12) C8 0.0425(13) 0.0410(15) 0.0465(14) 0.0034(12) -0.0020(11) 0.0002(11) C11 0.0467(14) 0.0400(15) 0.0474(14) 0.0017(13) -0.0071(11) -0.0055(11) C12 0.0577(16) 0.0526(17) 0.0546(16) 0.0035(14) -0.0013(13) -0.0122(13) C13 0.0623(18) 0.0517(18) 0.076(2) 0.0068(17) -0.0028(16) -0.0224(14) C14 0.0540(15) 0.0434(16) 0.076(2) -0.0067(16) -0.0167(14) -0.0143(13) C15 0.0331(10) 0.0339(13) 0.0426(12) 0.0011(11) 0.0018(10) -0.0057(10) C20 0.0449(13) 0.0398(15) 0.0505(15) -0.0077(13) 0.0086(11) -0.0077(12) C19 0.0452(13) 0.0458(16) 0.0524(16) -0.0073(13) -0.0076(11) 0.0053(11) C16 0.0408(12) 0.0421(15) 0.0420(14) 0.0004(12) 0.0010(10) -0.0119(11) C18 0.0487(14) 0.0571(19) 0.073(2) -0.0040(17) -0.0081(14) 0.0122(13) C17 0.0530(14) 0.0423(15) 0.0734(19) -0.0027(16) 0.0167(13) 0.0089(12) N2 0.0797(18) 0.0576(18) 0.0673(17) -0.0189(15) 0.0132(14) -0.0148(15) O3 0.0981(16) 0.0832(16) 0.0761(16) -0.0328(14) -0.0130(13) -0.0086(14) O2 0.158(2) 0.0527(15) 0.114(2) -0.0338(15) -0.0044(18) 0.0137(16) C21 0.0417(13) 0.0538(17) 0.0575(17) 0.0118(14) -0.0041(11) 0.0065(12) C24 0.0460(13) 0.0527(17) 0.0575(17) 0.0093(14) 0.0069(12) -0.0047(12) C23 0.0420(14) 0.068(2) 0.0691(19) 0.0018(16) 0.0084(13) 0.0035(13) C22 0.0384(13) 0.0668(19) 0.075(2) 0.0073(16) -0.0044(13) 0.0071(13) _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 C6 1.367(3) . ? O1 C8 1.479(3) . ? N1 C8 1.437(3) . ? N1 C21 1.470(3) . ? N1 C10 1.485(3) . ? C2 C11 1.420(3) . ? C2 C3 1.428(3) . ? C2 C1 1.431(3) . ? C6 C1 1.382(3) . ? C6 C5 1.417(3) . ? C1 C10 1.516(3) . ? C3 C14 1.412(3) . ? C3 C4 1.422(4) . ? C5 C4 1.350(3) . ? C10 C15 1.523(3) . ? C8 C24 1.506(3) . ? C11 C12 1.372(3) . ? C12 C13 1.398(4) . ? C13 C14 1.362(4) . ? C15 C19 1.384(3) . ? C15 C16 1.397(3) . ? C20 C16 1.374(3) . ? C20 C17 1.376(4) . ? C20 N2 1.474(4) . ? C19 C18 1.391(3) . ? C18 C17 1.379(4) . ? N2 O2 1.217(3) . ? N2 O3 1.229(3) . ? C21 C22 1.514(3) . ? C24 C23 1.517(3) . ? C23 C22 1.521(4) . ? 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 C6 O1 C8 115.44(16) . . ? C8 N1 C21 114.54(19) . . ? C8 N1 C10 111.06(17) . . ? C21 N1 C10 113.10(17) . . ? C11 C2 C3 117.8(2) . . ? C11 C2 C1 122.8(2) . . ? C3 C2 C1 119.4(2) . . ? O1 C6 C1 123.6(2) . . ? O1 C6 C5 115.2(2) . . ? C1 C6 C5 121.2(2) . . ? C6 C1 C2 119.1(2) . . ? C6 C1 C10 119.6(2) . . ? C2 C1 C10 121.3(2) . . ? C14 C3 C4 122.2(2) . . ? C14 C3 C2 119.2(2) . . ? C4 C3 C2 118.6(2) . . ? C4 C5 C6 120.2(2) . . ? N1 C10 C1 110.77(18) . . ? N1 C10 C15 107.85(17) . . ? C1 C10 C15 114.38(17) . . ? C5 C4 C3 121.5(2) . . ? N1 C8 O1 113.01(19) . . ? N1 C8 C24 113.4(2) . . ? O1 C8 C24 106.34(19) . . ? C12 C11 C2 121.1(2) . . ? C11 C12 C13 120.6(3) . . ? C14 C13 C12 120.1(3) . . ? C13 C14 C3 121.2(2) . . ? C19 C15 C16 118.7(2) . . ? C19 C15 C10 123.3(2) . . ? C16 C15 C10 117.8(2) . . ? C16 C20 C17 122.6(2) . . ? C16 C20 N2 118.6(2) . . ? C17 C20 N2 118.8(3) . . ? C15 C19 C18 120.9(2) . . ? C20 C16 C15 119.2(2) . . ? C17 C18 C19 120.3(2) . . ? C20 C17 C18 118.3(3) . . ? O2 N2 O3 123.3(3) . . ? O2 N2 C20 118.6(3) . . ? O3 N2 C20 118.1(3) . . ? N1 C21 C22 110.2(2) . . ? C8 C24 C23 111.8(2) . . ? C24 C23 C22 109.5(2) . . ? C21 C22 C23 110.1(2) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.282 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 952465'