# 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_ch14674 #TrackingRef 'ch14674.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H14 O3' _chemical_formula_sum 'C23 H14 O3' _chemical_formula_weight 338.34 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' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5890(7) _cell_length_b 9.7155(6) _cell_length_c 10.3144(7) _cell_angle_alpha 62.929(3) _cell_angle_beta 81.411(4) _cell_angle_gamma 84.972(5) _cell_volume 845.83(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour orange-yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9608 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 7023 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.14 _reflns_number_total 3005 _reflns_number_gt 2101 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0944P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3005 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1690 _refine_ls_wR_factor_gt 0.1275 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 C1 C 0.2761(3) 0.9744(3) -0.2434(2) 0.0379(6) Uani 1 1 d . . . C2 C 0.3205(2) 0.9069(3) -0.3472(2) 0.0386(6) Uani 1 1 d . . . C3 C 0.3257(3) 0.9777(3) -0.4992(3) 0.0476(7) Uani 1 1 d . . . H3 H 0.2937 1.0792 -0.5498 0.057 Uiso 1 1 calc R . . C4 C 0.3800(3) 0.8922(4) -0.5721(3) 0.0547(8) Uani 1 1 d . . . H4 H 0.3832 0.9363 -0.6736 0.066 Uiso 1 1 calc R . . C5 C 0.4299(3) 0.7416(4) -0.4968(3) 0.0561(8) Uani 1 1 d . . . H5 H 0.4695 0.6881 -0.5491 0.067 Uiso 1 1 calc R . . C6 C 0.4219(3) 0.6699(3) -0.3459(3) 0.0494(7) Uani 1 1 d . . . H6 H 0.4537 0.5684 -0.2954 0.059 Uiso 1 1 calc R . . C7 C 0.3649(2) 0.7546(3) -0.2722(2) 0.0389(6) Uani 1 1 d . . . C8 C 0.3400(2) 0.7060(3) -0.1121(2) 0.0367(6) Uani 1 1 d . . . C9 C 0.2906(2) 0.8463(3) -0.0938(2) 0.0344(6) Uani 1 1 d . . . C10 C 0.2610(2) 0.8469(3) 0.0379(2) 0.0342(6) Uani 1 1 d . . . C11 C 0.2774(3) 0.6978(3) 0.1773(2) 0.0349(6) Uani 1 1 d . . . C12 C 0.1599(3) 0.5877(3) 0.2465(2) 0.0360(6) Uani 1 1 d . . . C13 C 0.1755(3) 0.4548(3) 0.3759(2) 0.0439(6) Uani 1 1 d . . . H13 H 0.2585 0.4364 0.4184 0.053 Uiso 1 1 calc R . . C14 C 0.0684(3) 0.3500(3) 0.4415(3) 0.0527(7) Uani 1 1 d . . . H14 H 0.0791 0.2613 0.5283 0.063 Uiso 1 1 calc R . . C15 C -0.0531(3) 0.3761(3) 0.3799(3) 0.0576(8) Uani 1 1 d . . . H15 H -0.1249 0.3047 0.4246 0.069 Uiso 1 1 calc R . . C16 C -0.0709(3) 0.5071(3) 0.2520(3) 0.0615(8) Uani 1 1 d . . . H16 H -0.1543 0.5243 0.2106 0.074 Uiso 1 1 calc R . . C17 C 0.0357(3) 0.6128(3) 0.1855(3) 0.0501(7) Uani 1 1 d . . . H17 H 0.0238 0.7016 0.0990 0.060 Uiso 1 1 calc R . . C18 C 0.2303(2) 0.9853(3) 0.0637(2) 0.0338(6) Uani 1 1 d . . . C19 C 0.1176(3) 0.9874(3) 0.1660(3) 0.0466(7) Uani 1 1 d . . . H19 H 0.0566 0.9047 0.2130 0.056 Uiso 1 1 calc R . . C20 C 0.0968(3) 1.1122(3) 0.1971(3) 0.0539(8) Uani 1 1 d . . . H20 H 0.0204 1.1142 0.2634 0.065 Uiso 1 1 calc R . . C21 C 0.1879(3) 1.2336(3) 0.1312(3) 0.0525(7) Uani 1 1 d . . . H21 H 0.1741 1.3167 0.1536 0.063 Uiso 1 1 calc R . . C22 C 0.3004(3) 1.2311(3) 0.0312(3) 0.0483(7) Uani 1 1 d . . . H22 H 0.3628 1.3125 -0.0130 0.058 Uiso 1 1 calc R . . C23 C 0.3206(3) 1.1093(3) -0.0034(2) 0.0394(6) Uani 1 1 d . . . H23 H 0.3955 1.1100 -0.0724 0.047 Uiso 1 1 calc R . . O1 O 0.2345(2) 1.1064(2) -0.27617(18) 0.0544(5) Uani 1 1 d . . . O2 O 0.3553(2) 0.57674(19) -0.01434(18) 0.0517(5) Uani 1 1 d . . . O3 O 0.38635(19) 0.6800(2) 0.23117(18) 0.0489(5) 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 C1 0.0370(14) 0.0356(14) 0.0385(13) -0.0143(11) -0.0050(10) 0.0005(11) C2 0.0362(14) 0.0438(15) 0.0359(12) -0.0176(12) -0.0031(10) -0.0048(11) C3 0.0456(16) 0.0573(18) 0.0402(13) -0.0208(13) -0.0063(11) -0.0069(13) C4 0.0511(17) 0.078(2) 0.0398(14) -0.0300(15) -0.0020(12) -0.0110(16) C5 0.0528(18) 0.078(2) 0.0555(17) -0.0471(17) -0.0012(14) -0.0044(16) C6 0.0479(16) 0.0537(17) 0.0568(16) -0.0347(14) -0.0048(12) 0.0024(13) C7 0.0374(14) 0.0440(15) 0.0399(13) -0.0231(12) -0.0035(10) -0.0025(11) C8 0.0395(14) 0.0315(14) 0.0395(13) -0.0165(12) -0.0035(10) -0.0025(11) C9 0.0400(14) 0.0300(13) 0.0341(12) -0.0155(10) -0.0038(10) -0.0004(10) C10 0.0327(13) 0.0327(13) 0.0361(12) -0.0143(11) -0.0027(10) -0.0032(10) C11 0.0426(15) 0.0336(13) 0.0330(12) -0.0185(11) -0.0080(11) 0.0038(11) C12 0.0407(14) 0.0314(13) 0.0353(12) -0.0147(11) -0.0042(10) 0.0005(11) C13 0.0471(15) 0.0417(15) 0.0345(12) -0.0107(12) -0.0066(11) 0.0058(12) C14 0.0566(18) 0.0381(15) 0.0429(14) -0.0037(12) 0.0030(13) 0.0020(13) C15 0.0505(18) 0.0436(17) 0.0631(17) -0.0118(14) 0.0021(15) -0.0093(14) C16 0.0471(17) 0.0557(19) 0.0641(18) -0.0076(15) -0.0149(14) -0.0106(14) C17 0.0516(17) 0.0398(15) 0.0468(14) -0.0060(12) -0.0131(13) -0.0055(13) C18 0.0388(13) 0.0308(13) 0.0328(11) -0.0152(10) -0.0065(10) 0.0037(10) C19 0.0465(16) 0.0444(15) 0.0496(15) -0.0234(13) 0.0019(12) -0.0039(12) C20 0.0569(18) 0.0555(18) 0.0565(16) -0.0351(15) 0.0010(14) 0.0071(15) C21 0.068(2) 0.0412(16) 0.0592(16) -0.0316(14) -0.0160(14) 0.0096(14) C22 0.0611(18) 0.0332(14) 0.0518(15) -0.0184(13) -0.0113(13) -0.0038(13) C23 0.0457(15) 0.0331(13) 0.0388(12) -0.0161(11) -0.0022(11) -0.0026(11) O1 0.0739(13) 0.0385(11) 0.0460(10) -0.0155(9) -0.0133(9) 0.0132(10) O2 0.0732(13) 0.0329(10) 0.0465(10) -0.0167(9) -0.0063(9) 0.0038(9) O3 0.0496(11) 0.0480(11) 0.0498(10) -0.0197(9) -0.0169(9) -0.0003(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 C1 O1 1.214(3) . ? C1 C2 1.488(3) . ? C1 C9 1.495(3) . ? C2 C7 1.383(3) . ? C2 C3 1.391(3) . ? C3 C4 1.380(4) . ? C3 H3 0.9300 . ? C4 C5 1.388(4) . ? C4 H4 0.9300 . ? C5 C6 1.379(4) . ? C5 H5 0.9300 . ? C6 C7 1.386(3) . ? C6 H6 0.9300 . ? C7 C8 1.483(3) . ? C8 O2 1.214(3) . ? C8 C9 1.487(3) . ? C9 C10 1.348(3) . ? C10 C18 1.483(3) . ? C10 C11 1.524(3) . ? C11 O3 1.218(3) . ? C11 C12 1.484(3) . ? C12 C17 1.381(4) . ? C12 C13 1.389(3) . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.360(4) . ? C14 H14 0.9300 . ? C15 C16 1.374(4) . ? C15 H15 0.9300 . ? C16 C17 1.379(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C23 1.388(3) . ? C18 C19 1.398(3) . ? C19 C20 1.381(4) . ? C19 H19 0.9300 . ? C20 C21 1.374(4) . ? C20 H20 0.9300 . ? C21 C22 1.383(4) . ? C21 H21 0.9300 . ? C22 C23 1.374(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 O1 C1 C2 125.9(2) . . ? O1 C1 C9 128.2(2) . . ? C2 C1 C9 105.87(19) . . ? C7 C2 C3 120.8(2) . . ? C7 C2 C1 110.3(2) . . ? C3 C2 C1 128.8(2) . . ? C4 C3 C2 117.7(3) . . ? C4 C3 H3 121.2 . . ? C2 C3 H3 121.2 . . ? C3 C4 C5 121.2(2) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 121.2(2) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 117.6(3) . . ? C5 C6 H6 121.2 . . ? C7 C6 H6 121.2 . . ? C2 C7 C6 121.3(2) . . ? C2 C7 C8 109.6(2) . . ? C6 C7 C8 129.1(2) . . ? O2 C8 C7 127.0(2) . . ? O2 C8 C9 126.4(2) . . ? C7 C8 C9 106.65(19) . . ? C10 C9 C8 123.4(2) . . ? C10 C9 C1 129.3(2) . . ? C8 C9 C1 107.24(18) . . ? C9 C10 C18 126.2(2) . . ? C9 C10 C11 119.6(2) . . ? C18 C10 C11 113.68(18) . . ? O3 C11 C12 123.1(2) . . ? O3 C11 C10 116.8(2) . . ? C12 C11 C10 120.0(2) . . ? C17 C12 C13 119.0(2) . . ? C17 C12 C11 121.9(2) . . ? C13 C12 C11 119.1(2) . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.6(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C17 119.7(3) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 120.4(3) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? C23 C18 C19 118.8(2) . . ? C23 C18 C10 120.3(2) . . ? C19 C18 C10 120.6(2) . . ? C20 C19 C18 120.0(2) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 120.7(2) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C22 119.4(2) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 120.5(2) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C18 120.5(2) . . ? C22 C23 H23 119.7 . . ? C18 C23 H23 119.7 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.219 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 935870' ####################################################################### # # 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_14865 #TrackingRef '14865.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H24 N2 O5' _chemical_formula_sum 'C29 H24 N2 O5' _chemical_formula_weight 480.50 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' 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 12.4059(11) _cell_length_b 19.6766(16) _cell_length_c 10.5992(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.927(3) _cell_angle_gamma 90.00 _cell_volume 2432.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.69 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9402 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 13245 _diffrn_reflns_av_R_equivalents 0.0716 _diffrn_reflns_av_sigmaI/netI 0.0833 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.13 _reflns_number_total 4311 _reflns_number_gt 2660 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0758P)^2^+0.6209P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4311 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1083 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1712 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 C1 C 0.1461(2) 0.00827(15) 0.1762(3) 0.0327(7) Uani 1 1 d . . . C2 C 0.1450(3) 0.02218(16) 0.3020(3) 0.0383(8) Uani 1 1 d . . . H2 H 0.1240 -0.0116 0.3533 0.046 Uiso 1 1 calc R . . C3 C 0.1753(3) 0.08705(16) 0.3525(3) 0.0368(8) Uani 1 1 d . . . H3 H 0.1768 0.0976 0.4406 0.044 Uiso 1 1 calc R . . C4 C 0.2033(2) 0.13665(14) 0.2767(3) 0.0269(7) Uani 1 1 d . . . C5 C 0.2063(2) 0.11999(16) 0.1510(3) 0.0334(7) Uani 1 1 d . . . H5 H 0.2276 0.1535 0.0993 0.040 Uiso 1 1 calc R . . C6 C 0.1786(3) 0.05493(16) 0.0997(3) 0.0377(8) Uani 1 1 d . . . H6 H 0.1821 0.0430 0.0143 0.045 Uiso 1 1 calc R . . C7 C 0.2340(2) 0.20654(15) 0.3286(3) 0.0265(7) Uani 1 1 d . . . C8 C 0.3285(2) 0.21036(14) 0.4642(3) 0.0288(7) Uani 1 1 d . . . C9 C 0.4514(2) 0.21374(16) 0.4714(3) 0.0349(8) Uani 1 1 d . . . H9 H 0.4573 0.2456 0.4006 0.042 Uiso 1 1 calc R . . C10 C 0.4907(3) 0.14242(18) 0.4442(4) 0.0510(10) Uani 1 1 d . . . H10A H 0.4760 0.1093 0.5068 0.061 Uiso 1 1 calc R . . H10B H 0.4454 0.1283 0.3516 0.061 Uiso 1 1 calc R . . C11 C 0.6178(3) 0.1415(2) 0.4615(4) 0.0634(12) Uani 1 1 d . . . H11A H 0.6411 0.0944 0.4504 0.076 Uiso 1 1 calc R . . H11B H 0.6308 0.1698 0.3909 0.076 Uiso 1 1 calc R . . C12 C 0.6908(3) 0.1677(2) 0.5976(4) 0.0613(11) Uani 1 1 d . . . H12A H 0.7723 0.1685 0.6039 0.074 Uiso 1 1 calc R . . H12B H 0.6836 0.1371 0.6684 0.074 Uiso 1 1 calc R . . C13 C 0.6529(3) 0.2389(2) 0.6188(4) 0.0652(12) Uani 1 1 d . . . H13A H 0.7008 0.2555 0.7085 0.078 Uiso 1 1 calc R . . H13B H 0.6641 0.2699 0.5507 0.078 Uiso 1 1 calc R . . C14 C 0.5281(3) 0.23960(18) 0.6079(3) 0.0472(9) Uani 1 1 d . . . H14A H 0.5053 0.2865 0.6214 0.057 Uiso 1 1 calc R . . H14B H 0.5177 0.2106 0.6793 0.057 Uiso 1 1 calc R . . C15 C 0.1817(2) 0.26287(15) 0.2630(3) 0.0282(7) Uani 1 1 d . . . C16 C 0.2281(2) 0.33203(15) 0.3087(3) 0.0288(7) Uani 1 1 d . . . C17 C 0.0690(2) 0.34285(15) 0.1161(3) 0.0303(7) Uani 1 1 d . . . C18 C -0.0180(2) 0.36882(17) 0.0079(3) 0.0397(8) Uani 1 1 d . . . H18 H -0.0250 0.4163 -0.0092 0.048 Uiso 1 1 calc R . . C19 C -0.0944(3) 0.32330(19) -0.0746(4) 0.0544(10) Uani 1 1 d . . . H19 H -0.1538 0.3397 -0.1516 0.065 Uiso 1 1 calc R . . C20 C -0.0866(3) 0.2540(2) -0.0478(4) 0.0605(11) Uani 1 1 d . . . H20 H -0.1414 0.2239 -0.1052 0.073 Uiso 1 1 calc R . . C21 C 0.0007(3) 0.22849(18) 0.0622(4) 0.0468(9) Uani 1 1 d . . . H21 H 0.0056 0.1812 0.0812 0.056 Uiso 1 1 calc R . . C22 C 0.0807(2) 0.27321(15) 0.1441(3) 0.0312(7) Uani 1 1 d . . . C23 C 0.1761(3) 0.44953(15) 0.2141(3) 0.0338(7) Uani 1 1 d . . . C24 C 0.2933(2) 0.47784(15) 0.2702(3) 0.0319(7) Uani 1 1 d . . . C25 C 0.3868(3) 0.44801(17) 0.2473(3) 0.0381(8) Uani 1 1 d . . . H25 H 0.3785 0.4053 0.2030 0.046 Uiso 1 1 calc R . . C26 C 0.4917(3) 0.48067(19) 0.2890(4) 0.0479(9) Uani 1 1 d . . . H26 H 0.5550 0.4611 0.2711 0.057 Uiso 1 1 calc R . . C27 C 0.5045(3) 0.5416(2) 0.3565(4) 0.0535(10) Uani 1 1 d . . . H27 H 0.5769 0.5637 0.3858 0.064 Uiso 1 1 calc R . . C28 C 0.4127(3) 0.57062(18) 0.3818(4) 0.0536(10) Uani 1 1 d . . . H28 H 0.4227 0.6120 0.4306 0.064 Uiso 1 1 calc R . . C29 C 0.3063(3) 0.53974(16) 0.3364(3) 0.0425(8) Uani 1 1 d . . . H29 H 0.2424 0.5608 0.3504 0.051 Uiso 1 1 calc R . . N1 N 0.1103(2) -0.05948(15) 0.1194(3) 0.0452(7) Uani 1 1 d . . . N2 N 0.16185(18) 0.37832(12) 0.2119(2) 0.0280(6) Uani 1 1 d . . . O1 O 0.1272(3) -0.07477(15) 0.0176(3) 0.0920(11) Uani 1 1 d . . . O2 O 0.0621(2) -0.09625(12) 0.1745(3) 0.0617(7) Uani 1 1 d . . . O3 O 0.30184(18) 0.20376(11) 0.5636(2) 0.0401(6) Uani 1 1 d . . . O4 O 0.30688(17) 0.34698(10) 0.4095(2) 0.0344(5) Uani 1 1 d . . . O5 O 0.09375(19) 0.48538(11) 0.1630(3) 0.0557(7) 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 C1 0.0278(16) 0.0301(18) 0.0364(19) -0.0026(15) 0.0062(15) -0.0020(13) C2 0.0438(19) 0.0313(19) 0.041(2) 0.0011(15) 0.0161(16) -0.0086(15) C3 0.0415(18) 0.040(2) 0.0303(18) -0.0024(15) 0.0140(15) -0.0082(15) C4 0.0221(14) 0.0310(17) 0.0261(16) -0.0024(13) 0.0064(13) -0.0002(12) C5 0.0359(17) 0.0360(19) 0.0287(17) -0.0002(14) 0.0114(14) -0.0035(14) C6 0.0395(18) 0.043(2) 0.0297(18) -0.0068(15) 0.0108(15) -0.0025(15) C7 0.0234(15) 0.0321(18) 0.0254(16) -0.0005(13) 0.0100(13) -0.0013(12) C8 0.0331(17) 0.0282(17) 0.0246(16) 0.0010(13) 0.0092(14) -0.0010(13) C9 0.0280(16) 0.043(2) 0.0292(17) 0.0027(15) 0.0044(14) -0.0020(14) C10 0.0341(18) 0.063(3) 0.051(2) -0.0195(19) 0.0079(17) 0.0024(17) C11 0.040(2) 0.089(3) 0.057(3) -0.016(2) 0.0106(19) 0.011(2) C12 0.0336(19) 0.086(3) 0.053(2) -0.002(2) 0.0008(18) 0.0123(19) C13 0.036(2) 0.083(3) 0.061(3) -0.013(2) -0.0038(19) -0.009(2) C14 0.038(2) 0.049(2) 0.045(2) -0.0111(17) 0.0014(17) -0.0023(16) C15 0.0233(15) 0.0311(17) 0.0301(17) -0.0015(14) 0.0088(14) -0.0033(13) C16 0.0263(15) 0.0347(18) 0.0264(17) -0.0004(14) 0.0105(14) -0.0004(13) C17 0.0201(14) 0.0336(18) 0.0353(17) -0.0002(14) 0.0071(13) -0.0005(13) C18 0.0274(16) 0.039(2) 0.044(2) 0.0041(16) 0.0015(15) 0.0030(14) C19 0.0337(19) 0.056(2) 0.052(2) 0.0024(19) -0.0120(17) 0.0071(17) C20 0.039(2) 0.047(2) 0.067(3) -0.008(2) -0.0180(19) -0.0014(17) C21 0.0333(18) 0.037(2) 0.053(2) -0.0044(17) -0.0079(17) -0.0017(15) C22 0.0206(15) 0.0340(18) 0.0338(18) -0.0001(14) 0.0027(14) -0.0010(13) C23 0.0332(17) 0.0304(18) 0.0374(19) 0.0015(15) 0.0114(15) 0.0022(14) C24 0.0334(17) 0.0310(18) 0.0272(17) 0.0039(14) 0.0051(14) -0.0037(13) C25 0.0386(18) 0.041(2) 0.0332(18) -0.0007(15) 0.0104(15) -0.0044(15) C26 0.0359(19) 0.060(3) 0.047(2) 0.0037(19) 0.0121(17) -0.0093(17) C27 0.050(2) 0.058(3) 0.042(2) 0.0055(19) 0.0019(18) -0.0267(19) C28 0.072(3) 0.040(2) 0.040(2) -0.0016(17) 0.008(2) -0.021(2) C29 0.056(2) 0.0305(19) 0.039(2) 0.0008(15) 0.0130(17) -0.0027(16) N1 0.0442(17) 0.0414(18) 0.0494(19) -0.0095(15) 0.0151(15) -0.0081(14) N2 0.0227(12) 0.0278(14) 0.0292(14) 0.0000(11) 0.0035(11) 0.0005(10) O1 0.141(3) 0.068(2) 0.098(2) -0.0472(18) 0.081(2) -0.0495(19) O2 0.0791(18) 0.0417(16) 0.0645(18) -0.0050(13) 0.0248(16) -0.0197(14) O3 0.0445(13) 0.0508(15) 0.0262(12) 0.0041(10) 0.0137(11) -0.0026(10) O4 0.0345(12) 0.0373(13) 0.0255(12) -0.0032(9) 0.0027(10) -0.0040(9) O5 0.0366(13) 0.0336(14) 0.085(2) 0.0053(13) 0.0048(13) 0.0063(11) _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 C1 C2 1.366(4) . ? C1 C6 1.373(4) . ? C1 N1 1.468(4) . ? C2 C3 1.386(4) . ? C2 H2 0.9500 . ? C3 C4 1.382(4) . ? C3 H3 0.9500 . ? C4 C5 1.384(4) . ? C4 C7 1.482(4) . ? C5 C6 1.387(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C15 1.351(4) . ? C7 C8 1.515(4) . ? C8 O3 1.213(3) . ? C8 C9 1.502(4) . ? C9 C14 1.523(4) . ? C9 C10 1.545(4) . ? C9 H9 1.0000 . ? C10 C11 1.524(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.509(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.517(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.514(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C22 1.457(4) . ? C15 C16 1.493(4) . ? C16 O4 1.213(3) . ? C16 N2 1.408(4) . ? C17 C18 1.377(4) . ? C17 C22 1.399(4) . ? C17 N2 1.431(4) . ? C18 C19 1.379(5) . ? C18 H18 0.9500 . ? C19 C20 1.389(5) . ? C19 H19 0.9500 . ? C20 C21 1.387(5) . ? C20 H20 0.9500 . ? C21 C22 1.388(4) . ? C21 H21 0.9500 . ? C23 O5 1.207(3) . ? C23 N2 1.411(4) . ? C23 C24 1.480(4) . ? C24 C25 1.393(4) . ? C24 C29 1.387(4) . ? C25 C26 1.382(4) . ? C25 H25 0.9500 . ? C26 C27 1.377(5) . ? C26 H26 0.9500 . ? C27 C28 1.380(5) . ? C27 H27 0.9500 . ? C28 C29 1.383(5) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? N1 O1 1.205(4) . ? N1 O2 1.209(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 C2 C1 C6 123.0(3) . . ? C2 C1 N1 118.7(3) . . ? C6 C1 N1 118.3(3) . . ? C1 C2 C3 118.0(3) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 119.1(3) . . ? C3 C4 C7 121.5(3) . . ? C5 C4 C7 119.3(3) . . ? C6 C5 C4 120.7(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C1 C6 C5 118.0(3) . . ? C1 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? C15 C7 C4 123.5(3) . . ? C15 C7 C8 121.9(3) . . ? C4 C7 C8 114.6(2) . . ? O3 C8 C9 122.2(3) . . ? O3 C8 C7 117.8(2) . . ? C9 C8 C7 119.6(2) . . ? C8 C9 C14 110.9(2) . . ? C8 C9 C10 109.3(2) . . ? C14 C9 C10 110.3(3) . . ? C8 C9 H9 108.8 . . ? C14 C9 H9 108.8 . . ? C10 C9 H9 108.8 . . ? C11 C10 C9 111.6(3) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 111.7(3) . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 110.0(3) . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C14 C13 C12 111.0(3) . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C13 C14 C9 111.1(3) . . ? C13 C14 H14A 109.4 . . ? C9 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? C9 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C7 C15 C22 132.9(3) . . ? C7 C15 C16 121.1(3) . . ? C22 C15 C16 106.0(2) . . ? O4 C16 N2 125.4(3) . . ? O4 C16 C15 127.8(3) . . ? N2 C16 C15 106.8(2) . . ? C18 C17 C22 122.4(3) . . ? C18 C17 N2 128.5(3) . . ? C22 C17 N2 109.1(2) . . ? C19 C18 C17 117.5(3) . . ? C19 C18 H18 121.3 . . ? C17 C18 H18 121.3 . . ? C18 C19 C20 121.5(3) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? C19 C20 C21 120.5(3) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C22 118.9(3) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C21 C22 C17 119.2(3) . . ? C21 C22 C15 132.3(3) . . ? C17 C22 C15 108.5(3) . . ? O5 C23 N2 119.4(3) . . ? O5 C23 C24 121.7(3) . . ? N2 C23 C24 118.7(3) . . ? C25 C24 C29 119.9(3) . . ? C25 C24 C23 122.3(3) . . ? C29 C24 C23 117.5(3) . . ? C26 C25 C24 119.8(3) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C27 C26 C25 120.0(3) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 120.3(3) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C29 120.3(3) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C28 C29 C24 119.6(3) . . ? C28 C29 H29 120.2 . . ? C24 C29 H29 120.2 . . ? O1 N1 O2 123.3(3) . . ? O1 N1 C1 118.3(3) . . ? O2 N1 C1 118.4(3) . . ? C16 N2 C23 126.3(2) . . ? C16 N2 C17 109.3(2) . . ? C23 N2 C17 124.2(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.233 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 935871' ####################################################################### # # 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_ch14840 #TrackingRef 'ch14840.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H15 N O4' _chemical_formula_sum 'C26 H15 N O4' _chemical_formula_weight 405.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' 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 31.751(8) _cell_length_b 10.414(3) _cell_length_c 12.219(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.638(6) _cell_angle_gamma 90.00 _cell_volume 4027.2(18) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9820 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 12096 _diffrn_reflns_av_R_equivalents 0.0768 _diffrn_reflns_av_sigmaI/netI 0.1144 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3552 _reflns_number_gt 1436 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1505P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3552 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1953 _refine_ls_R_factor_gt 0.0768 _refine_ls_wR_factor_ref 0.2928 _refine_ls_wR_factor_gt 0.2104 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.007 _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 C1 C 0.42112(18) 0.3815(6) 0.2442(4) 0.0645(16) Uani 1 1 d . A . C2 C 0.42796(18) 0.4005(6) 0.3550(5) 0.0756(17) Uani 1 1 d . . . H2 H 0.4446 0.4680 0.3836 0.091 Uiso 1 1 calc R . . C3 C 0.40929(17) 0.3161(6) 0.4219(4) 0.0651(16) Uani 1 1 d . . . H3 H 0.4143 0.3244 0.4976 0.078 Uiso 1 1 calc R . . C4 C 0.38320(15) 0.2189(5) 0.3801(4) 0.0535(14) Uani 1 1 d . . . C5 C 0.37721(16) 0.2052(6) 0.2674(4) 0.0632(15) Uani 1 1 d . . . H5 H 0.3599 0.1397 0.2380 0.076 Uiso 1 1 calc R . . C6 C 0.39634(18) 0.2865(6) 0.1976(4) 0.0667(16) Uani 1 1 d . . . H6 H 0.3925 0.2769 0.1217 0.080 Uiso 1 1 calc R . . C7 C 0.36306(16) 0.1271(5) 0.4518(4) 0.0535(14) Uani 1 1 d . . . C8 C 0.39318(16) 0.0707(6) 0.5428(4) 0.0602(15) Uani 1 1 d . . . C9 C 0.42349(16) -0.0286(5) 0.5138(4) 0.0593(15) Uani 1 1 d . . . C10 C 0.45664(17) -0.0629(6) 0.5913(4) 0.0680(16) Uani 1 1 d . . . H10 H 0.4591 -0.0237 0.6599 0.082 Uiso 1 1 calc R . . C11 C 0.48506(19) -0.1532(7) 0.5663(6) 0.0787(18) Uani 1 1 d . . . H11 H 0.5071 -0.1752 0.6178 0.094 Uiso 1 1 calc R . . C12 C 0.4816(2) -0.2121(7) 0.4657(7) 0.093(2) Uani 1 1 d . . . H12 H 0.5013 -0.2739 0.4492 0.112 Uiso 1 1 calc R . . C13 C 0.4491(2) -0.1803(7) 0.3889(5) 0.090(2) Uani 1 1 d . . . H13 H 0.4469 -0.2197 0.3204 0.108 Uiso 1 1 calc R . . C14 C 0.41976(18) -0.0889(6) 0.4149(5) 0.0747(17) Uani 1 1 d . . . H14 H 0.3973 -0.0687 0.3641 0.090 Uiso 1 1 calc R . . C15 C 0.32167(16) 0.0993(5) 0.4459(4) 0.0566(14) Uani 1 1 d . . . C16 C 0.30368(18) -0.0086(6) 0.5092(4) 0.0653(16) Uani 1 1 d . . . C17 C 0.25698(17) -0.0031(6) 0.4860(5) 0.0639(15) Uani 1 1 d . . . C18 C 0.2250(2) -0.0751(6) 0.5225(5) 0.0840(19) Uani 1 1 d . . . H18 H 0.2307 -0.1438 0.5700 0.101 Uiso 1 1 calc R . . C19 C 0.1833(2) -0.0425(8) 0.4861(6) 0.099(2) Uani 1 1 d . . . H19 H 0.1611 -0.0901 0.5107 0.118 Uiso 1 1 calc R . . C20 C 0.1745(2) 0.0581(8) 0.4151(6) 0.096(2) Uani 1 1 d . . . H20 H 0.1465 0.0762 0.3920 0.115 Uiso 1 1 calc R . . C21 C 0.20680(18) 0.1346(6) 0.3763(5) 0.0682(17) Uani 1 1 d . . . C22 C 0.24803(17) 0.0982(6) 0.4142(4) 0.0578(14) Uani 1 1 d . . . C23 C 0.28474(16) 0.1624(5) 0.3842(4) 0.0568(14) Uani 1 1 d . . . C24 C 0.27969(18) 0.2681(6) 0.3169(4) 0.0712(17) Uani 1 1 d . . . H24 H 0.3030 0.3134 0.2961 0.085 Uiso 1 1 calc R . . C25 C 0.2381(2) 0.3064(6) 0.2801(4) 0.0797(19) Uani 1 1 d . . . H25 H 0.2346 0.3781 0.2350 0.096 Uiso 1 1 calc R . . C26 C 0.2028(2) 0.2428(7) 0.3080(5) 0.0794(19) Uani 1 1 d . . . H26 H 0.1761 0.2714 0.2816 0.095 Uiso 1 1 calc R . . N1 N 0.44017(19) 0.4708(6) 0.1692(5) 0.0950(18) Uani 1 1 d . . . O1' O 0.4728(4) 0.5304(13) 0.2147(10) 0.111(4) Uiso 0.40 1 d P A 1 O1 O 0.4449(3) 0.5855(9) 0.2004(7) 0.111(3) Uiso 0.60 1 d P A 2 O2 O 0.43859(18) 0.4500(5) 0.0759(4) 0.126(2) Uani 1 1 d . A . O3 O 0.39347(12) 0.1179(4) 0.6344(3) 0.0863(14) Uani 1 1 d . . . O4 O 0.32392(13) -0.0876(4) 0.5641(3) 0.0901(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 C1 0.065(4) 0.075(4) 0.056(4) 0.009(3) 0.021(3) 0.005(3) C2 0.076(4) 0.084(5) 0.067(4) -0.003(4) 0.010(3) -0.014(4) C3 0.069(4) 0.078(4) 0.050(3) -0.015(3) 0.013(3) -0.005(3) C4 0.044(3) 0.066(4) 0.050(3) 0.002(3) 0.001(2) 0.009(3) C5 0.067(4) 0.068(4) 0.054(3) -0.005(3) 0.000(3) 0.002(3) C6 0.078(4) 0.074(4) 0.049(3) -0.001(3) 0.010(3) 0.012(3) C7 0.049(3) 0.063(4) 0.049(3) -0.001(3) 0.005(2) 0.005(3) C8 0.055(3) 0.075(4) 0.049(3) -0.001(3) -0.005(3) -0.002(3) C9 0.052(3) 0.066(4) 0.058(3) 0.015(3) 0.000(3) -0.007(3) C10 0.055(4) 0.080(4) 0.068(4) 0.018(3) 0.005(3) -0.001(3) C11 0.058(4) 0.087(5) 0.091(5) 0.015(4) 0.006(3) 0.010(4) C12 0.083(5) 0.083(5) 0.118(6) 0.014(5) 0.030(4) 0.015(4) C13 0.097(5) 0.086(5) 0.088(5) -0.006(4) 0.008(4) 0.019(4) C14 0.066(4) 0.086(5) 0.071(4) -0.001(4) -0.005(3) 0.008(4) C15 0.055(3) 0.064(4) 0.049(3) 0.003(3) -0.004(2) 0.002(3) C16 0.064(4) 0.073(4) 0.057(3) 0.005(3) -0.003(3) -0.003(3) C17 0.052(4) 0.076(4) 0.064(3) -0.012(3) 0.002(3) -0.006(3) C18 0.079(5) 0.087(5) 0.087(4) -0.004(4) 0.012(4) -0.014(4) C19 0.065(5) 0.114(6) 0.117(6) -0.002(5) 0.011(4) -0.023(4) C20 0.057(4) 0.120(6) 0.110(6) -0.030(5) 0.002(4) -0.006(4) C21 0.055(4) 0.089(5) 0.059(3) -0.023(4) -0.005(3) 0.008(3) C22 0.059(4) 0.068(4) 0.045(3) -0.015(3) -0.006(3) 0.001(3) C23 0.058(4) 0.065(4) 0.046(3) 0.000(3) -0.005(3) 0.004(3) C24 0.071(4) 0.082(4) 0.061(3) 0.006(3) 0.003(3) 0.011(3) C25 0.090(5) 0.088(5) 0.059(4) 0.008(3) 0.000(3) 0.028(4) C26 0.071(5) 0.109(6) 0.057(4) -0.015(4) -0.008(3) 0.023(4) N1 0.117(5) 0.094(5) 0.077(4) 0.003(4) 0.028(4) 0.007(4) O2 0.201(6) 0.108(4) 0.075(3) 0.019(3) 0.053(3) 0.017(4) O3 0.076(3) 0.125(4) 0.055(2) -0.006(3) -0.0087(19) 0.025(3) O4 0.078(3) 0.097(3) 0.093(3) 0.037(3) -0.009(2) 0.009(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 C1 C6 1.360(7) . ? C1 C2 1.368(7) . ? C1 N1 1.469(8) . ? C2 C3 1.368(7) . ? C2 H2 0.9300 . ? C3 C4 1.380(7) . ? C3 H3 0.9300 . ? C4 C5 1.382(7) . ? C4 C7 1.476(7) . ? C5 C6 1.378(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C15 1.342(7) . ? C7 C8 1.525(7) . ? C8 O3 1.221(6) . ? C8 C9 1.475(7) . ? C9 C14 1.359(7) . ? C9 C10 1.405(7) . ? C10 C11 1.355(8) . ? C10 H10 0.9300 . ? C11 C12 1.371(8) . ? C11 H11 0.9300 . ? C12 C13 1.377(8) . ? C12 H12 0.9300 . ? C13 C14 1.387(8) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C23 1.494(7) . ? C15 C16 1.503(7) . ? C16 O4 1.213(6) . ? C16 C17 1.488(8) . ? C17 C18 1.366(8) . ? C17 C22 1.387(7) . ? C18 C19 1.403(9) . ? C18 H18 0.9300 . ? C19 C20 1.374(9) . ? C19 H19 0.9300 . ? C20 C21 1.411(9) . ? C20 H20 0.9300 . ? C21 C26 1.402(8) . ? C21 C22 1.405(7) . ? C22 C23 1.418(7) . ? C23 C24 1.375(7) . ? C24 C25 1.419(7) . ? C24 H24 0.9300 . ? C25 C26 1.368(8) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? N1 O2 1.158(6) . ? N1 O1' 1.293(13) . ? N1 O1 1.259(10) . ? 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 C1 C2 124.1(5) . . ? C6 C1 N1 116.9(5) . . ? C2 C1 N1 119.0(6) . . ? C3 C2 C1 117.2(6) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C2 C3 C4 121.8(5) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C3 C4 C5 118.3(5) . . ? C3 C4 C7 122.1(4) . . ? C5 C4 C7 119.6(5) . . ? C6 C5 C4 121.5(5) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C1 C6 C5 117.2(5) . . ? C1 C6 H6 121.4 . . ? C5 C6 H6 121.4 . . ? C15 C7 C4 125.2(5) . . ? C15 C7 C8 120.6(5) . . ? C4 C7 C8 114.0(4) . . ? O3 C8 C9 123.1(5) . . ? O3 C8 C7 118.1(5) . . ? C9 C8 C7 118.5(5) . . ? C14 C9 C10 119.3(6) . . ? C14 C9 C8 121.8(5) . . ? C10 C9 C8 119.0(5) . . ? C11 C10 C9 120.1(6) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.4(6) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 120.3(6) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 119.3(6) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C9 C14 C13 120.6(6) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C7 C15 C23 131.1(5) . . ? C7 C15 C16 123.0(5) . . ? C23 C15 C16 105.9(4) . . ? O4 C16 C17 127.3(6) . . ? O4 C16 C15 125.8(5) . . ? C17 C16 C15 106.7(5) . . ? C18 C17 C22 120.3(6) . . ? C18 C17 C16 132.3(6) . . ? C22 C17 C16 107.4(5) . . ? C17 C18 C19 118.1(6) . . ? C17 C18 H18 120.9 . . ? C19 C18 H18 120.9 . . ? C20 C19 C18 121.5(7) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C21 121.8(6) . . ? C19 C20 H20 119.1 . . ? C21 C20 H20 119.1 . . ? C26 C21 C22 116.8(6) . . ? C26 C21 C20 128.3(6) . . ? C22 C21 C20 114.8(6) . . ? C17 C22 C21 123.5(6) . . ? C17 C22 C23 113.1(5) . . ? C21 C22 C23 123.5(6) . . ? C24 C23 C22 118.3(5) . . ? C24 C23 C15 134.6(5) . . ? C22 C23 C15 106.9(5) . . ? C23 C24 C25 118.4(6) . . ? C23 C24 H24 120.8 . . ? C25 C24 H24 120.8 . . ? C26 C25 C24 123.1(6) . . ? C26 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? C25 C26 C21 120.0(6) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? O2 N1 O1' 118.9(8) . . ? O2 N1 O1 118.0(7) . . ? O1' N1 O1 48.9(6) . . ? O2 N1 C1 120.6(6) . . ? O1' N1 C1 113.0(7) . . ? O1 N1 C1 117.2(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.265 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 935872' ####################################################################### # # 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_a14925 #TrackingRef 'a14925.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H19 N O4' _chemical_formula_sum 'C25 H19 N O4' _chemical_formula_weight 397.41 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' 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 14.269(3) _cell_length_b 11.125(3) _cell_length_c 25.270(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.184(6) _cell_angle_gamma 90.00 _cell_volume 4011.4(14) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9441 _exptl_absorpt_correction_T_max 0.9973 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 22171 _diffrn_reflns_av_R_equivalents 0.1080 _diffrn_reflns_av_sigmaI/netI 0.1408 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.06 _reflns_number_total 7060 _reflns_number_gt 3346 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0662P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7060 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1579 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1811 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _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 C1 C 0.2156(2) 0.1697(4) 0.09182(14) 0.0345(10) Uani 1 1 d . . . C2 C 0.2091(2) 0.2915(4) 0.10046(14) 0.0350(10) Uani 1 1 d . . . H2 H 0.2357 0.3469 0.0762 0.042 Uiso 1 1 calc R . . C3 C 0.1629(2) 0.3318(3) 0.14543(13) 0.0316(9) Uani 1 1 d . . . H3 H 0.1575 0.4156 0.1519 0.038 Uiso 1 1 calc R . . C4 C 0.1245(2) 0.2503(3) 0.18084(13) 0.0256(9) Uani 1 1 d . . . C5 C 0.1312(2) 0.1281(3) 0.17055(14) 0.0319(9) Uani 1 1 d . . . H5 H 0.1037 0.0725 0.1944 0.038 Uiso 1 1 calc R . . C6 C 0.1771(2) 0.0858(4) 0.12621(14) 0.0348(10) Uani 1 1 d . . . H6 H 0.1822 0.0020 0.1195 0.042 Uiso 1 1 calc R . . C7 C 0.0713(2) 0.2920(3) 0.22785(14) 0.0258(9) Uani 1 1 d . . . C8 C -0.0145(2) 0.3648(3) 0.21239(13) 0.0272(9) Uani 1 1 d . . . C9 C -0.0991(2) 0.2956(3) 0.19525(13) 0.0269(9) Uani 1 1 d . . . C10 C -0.1085(2) 0.1739(3) 0.20563(13) 0.0314(9) Uani 1 1 d . . . H10 H -0.0619 0.1332 0.2257 0.038 Uiso 1 1 calc R . . C11 C -0.1857(2) 0.1115(4) 0.18677(15) 0.0392(10) Uani 1 1 d . . . H11 H -0.1919 0.0279 0.1937 0.047 Uiso 1 1 calc R . . C12 C -0.2532(3) 0.1708(4) 0.15805(14) 0.0421(11) Uani 1 1 d . . . H12 H -0.3061 0.1279 0.1451 0.051 Uiso 1 1 calc R . . C13 C -0.2448(3) 0.2926(4) 0.14783(14) 0.0415(11) Uani 1 1 d . . . H13 H -0.2916 0.3330 0.1278 0.050 Uiso 1 1 calc R . . C14 C -0.1684(2) 0.3554(4) 0.16680(13) 0.0328(10) Uani 1 1 d . . . H14 H -0.1631 0.4393 0.1604 0.039 Uiso 1 1 calc R . . C15 C 0.0926(2) 0.2679(3) 0.27843(14) 0.0272(9) Uani 1 1 d . . . C16 C 0.0282(2) 0.3044(3) 0.32226(14) 0.0304(9) Uani 1 1 d . . . C17 C 0.0680(2) 0.2610(3) 0.37512(13) 0.0301(9) Uani 1 1 d . . . C18 C 0.0810(3) 0.3690(4) 0.41266(14) 0.0471(11) Uani 1 1 d . . . H18A H 0.1064 0.3409 0.4465 0.071 Uiso 1 1 calc R . . H18B H 0.0203 0.4079 0.4185 0.071 Uiso 1 1 calc R . . H18C H 0.1244 0.4267 0.3967 0.071 Uiso 1 1 calc R . . C19 C -0.0002(2) 0.1693(4) 0.39903(14) 0.0420(11) Uani 1 1 d . . . H19A H 0.0242 0.1414 0.4332 0.063 Uiso 1 1 calc R . . H19B H -0.0069 0.1008 0.3750 0.063 Uiso 1 1 calc R . . H19C H -0.0615 0.2073 0.4042 0.063 Uiso 1 1 calc R . . C20 C 0.1601(2) 0.2040(3) 0.35866(13) 0.0262(9) Uani 1 1 d . . . C21 C 0.2278(3) 0.1538(3) 0.39118(14) 0.0350(10) Uani 1 1 d . . . H21 H 0.2197 0.1530 0.4285 0.042 Uiso 1 1 calc R . . C22 C 0.3076(3) 0.1048(3) 0.36861(16) 0.0406(11) Uani 1 1 d . . . H22 H 0.3538 0.0686 0.3906 0.049 Uiso 1 1 calc R . . C23 C 0.3207(2) 0.1080(4) 0.31465(16) 0.0402(11) Uani 1 1 d . . . H23 H 0.3761 0.0745 0.2999 0.048 Uiso 1 1 calc R . . C24 C 0.2545(2) 0.1592(3) 0.28173(14) 0.0318(10) Uani 1 1 d . . . H24 H 0.2640 0.1615 0.2446 0.038 Uiso 1 1 calc R . . C25 C 0.1734(2) 0.2075(3) 0.30367(13) 0.0270(9) Uani 1 1 d . . . C26 C 0.4716(2) 0.2512(4) 1.11195(14) 0.0335(10) Uani 1 1 d . . . C27 C 0.4845(2) 0.3684(4) 1.09611(14) 0.0363(10) Uani 1 1 d . . . H27 H 0.4592 0.4330 1.1160 0.044 Uiso 1 1 calc R . . C28 C 0.5351(2) 0.3899(4) 1.05056(14) 0.0350(10) Uani 1 1 d . . . H28 H 0.5458 0.4705 1.0396 0.042 Uiso 1 1 calc R . . C29 C 0.5708(2) 0.2954(4) 1.02035(13) 0.0285(9) Uani 1 1 d . . . C30 C 0.5555(2) 0.1772(4) 1.03744(14) 0.0346(10) Uani 1 1 d . . . H30 H 0.5791 0.1117 1.0174 0.042 Uiso 1 1 calc R . . C31 C 0.5060(2) 0.1556(4) 1.08350(15) 0.0371(10) Uani 1 1 d . . . H31 H 0.4959 0.0756 1.0953 0.044 Uiso 1 1 calc R . . C32 C 0.6287(2) 0.3215(3) 0.97286(14) 0.0293(9) Uani 1 1 d . . . C33 C 0.7137(2) 0.4009(4) 0.98636(14) 0.0339(10) Uani 1 1 d . . . C34 C 0.8009(2) 0.3399(4) 1.00455(13) 0.0310(9) Uani 1 1 d . . . C35 C 0.8739(2) 0.4090(4) 1.02443(14) 0.0418(11) Uani 1 1 d . . . H35 H 0.8696 0.4942 1.0241 0.050 Uiso 1 1 calc R . . C36 C 0.9531(3) 0.3538(5) 1.04473(15) 0.0514(13) Uani 1 1 d . . . H36 H 1.0028 0.4014 1.0584 0.062 Uiso 1 1 calc R . . C37 C 0.9603(3) 0.2314(5) 1.04532(16) 0.0552(13) Uani 1 1 d . . . H37 H 1.0143 0.1940 1.0600 0.066 Uiso 1 1 calc R . . C38 C 0.8882(3) 0.1616(4) 1.02431(16) 0.0524(12) Uani 1 1 d . . . H38 H 0.8938 0.0765 1.0238 0.063 Uiso 1 1 calc R . . C39 C 0.8090(3) 0.2157(4) 1.00425(15) 0.0433(11) Uani 1 1 d . . . H39 H 0.7597 0.1679 0.9902 0.052 Uiso 1 1 calc R . . C40 C 0.6108(2) 0.2858(3) 0.92277(14) 0.0325(10) Uani 1 1 d . . . C41 C 0.6770(3) 0.3169(4) 0.87851(15) 0.0381(10) Uani 1 1 d . . . C42 C 0.6383(3) 0.2678(4) 0.82621(14) 0.0352(10) Uani 1 1 d . . . C43 C 0.7074(3) 0.1772(4) 0.80232(16) 0.0586(13) Uani 1 1 d . . . H43A H 0.6827 0.1475 0.7685 0.088 Uiso 1 1 calc R . . H43B H 0.7158 0.1096 0.8268 0.088 Uiso 1 1 calc R . . H43C H 0.7679 0.2166 0.7964 0.088 Uiso 1 1 calc R . . C44 C 0.6207(3) 0.3731(4) 0.78797(15) 0.0503(12) Uani 1 1 d . . . H44A H 0.5967 0.3420 0.7543 0.075 Uiso 1 1 calc R . . H44B H 0.6796 0.4162 0.7818 0.075 Uiso 1 1 calc R . . H44C H 0.5747 0.4281 0.8034 0.075 Uiso 1 1 calc R . . C45 C 0.5479(2) 0.2076(3) 0.84383(14) 0.0325(10) Uani 1 1 d . . . C46 C 0.4834(3) 0.1498(4) 0.81205(15) 0.0416(11) Uani 1 1 d . . . H46 H 0.4947 0.1410 0.7752 0.050 Uiso 1 1 calc R . . C47 C 0.4026(3) 0.1051(4) 0.83397(17) 0.0469(12) Uani 1 1 d . . . H47 H 0.3583 0.0650 0.8121 0.056 Uiso 1 1 calc R . . C48 C 0.3848(3) 0.1178(3) 0.88778(16) 0.0424(11) Uani 1 1 d . . . H48 H 0.3284 0.0871 0.9024 0.051 Uiso 1 1 calc R . . C49 C 0.4495(2) 0.1753(3) 0.92016(15) 0.0371(10) Uani 1 1 d . . . H49 H 0.4377 0.1837 0.9570 0.044 Uiso 1 1 calc R . . C50 C 0.5320(2) 0.2209(3) 0.89845(14) 0.0323(10) Uani 1 1 d . . . N1 N 0.2670(2) 0.1259(4) 0.04502(15) 0.0500(10) Uani 1 1 d . . . N2 N 0.4211(2) 0.2293(4) 1.16168(14) 0.0460(10) Uani 1 1 d . . . O1 O 0.2823(2) 0.1967(4) 0.00951(13) 0.0841(12) Uani 1 1 d . . . O2 O 0.2933(2) 0.0217(4) 0.04490(14) 0.0817(11) Uani 1 1 d . . . O3 O -0.00909(16) 0.4742(2) 0.20899(10) 0.0409(7) Uani 1 1 d . . . O4 O -0.04576(17) 0.3570(2) 0.31714(9) 0.0422(7) Uani 1 1 d . . . O5 O 0.4069(2) 0.1243(4) 1.17393(12) 0.0761(11) Uani 1 1 d . . . O6 O 0.3964(2) 0.3160(3) 1.18846(11) 0.0679(10) Uani 1 1 d . . . O7 O 0.70332(17) 0.5102(3) 0.98745(10) 0.0494(8) Uani 1 1 d . . . O8 O 0.74938(19) 0.3729(3) 0.88354(10) 0.0577(9) 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 C1 0.033(2) 0.045(3) 0.025(2) -0.005(2) -0.0023(18) 0.001(2) C2 0.034(2) 0.046(3) 0.025(2) 0.010(2) -0.0012(18) -0.002(2) C3 0.035(2) 0.030(3) 0.031(2) 0.0070(19) -0.0026(19) -0.0025(18) C4 0.029(2) 0.027(2) 0.020(2) 0.0064(17) -0.0018(17) 0.0002(17) C5 0.036(2) 0.032(3) 0.027(2) 0.0033(19) 0.0007(18) -0.0022(18) C6 0.040(2) 0.025(2) 0.038(2) -0.007(2) -0.007(2) 0.0015(19) C7 0.029(2) 0.022(2) 0.027(2) 0.0013(17) 0.0032(17) -0.0016(16) C8 0.036(2) 0.025(3) 0.020(2) 0.0025(17) 0.0018(16) -0.0007(18) C9 0.028(2) 0.027(2) 0.026(2) 0.0010(17) 0.0017(16) 0.0024(17) C10 0.031(2) 0.031(3) 0.032(2) 0.0031(18) -0.0022(17) 0.0030(18) C11 0.043(2) 0.027(3) 0.048(3) -0.006(2) 0.000(2) -0.002(2) C12 0.038(2) 0.047(3) 0.041(3) -0.002(2) -0.002(2) -0.008(2) C13 0.041(2) 0.049(3) 0.035(2) 0.003(2) -0.0106(19) 0.004(2) C14 0.042(2) 0.030(3) 0.027(2) 0.0004(18) 0.0023(18) 0.0038(19) C15 0.030(2) 0.025(2) 0.026(2) -0.0010(17) 0.0019(17) -0.0042(17) C16 0.032(2) 0.029(3) 0.030(2) -0.0006(18) 0.0004(18) -0.0028(18) C17 0.043(2) 0.027(2) 0.020(2) 0.0017(17) 0.0011(18) -0.0045(18) C18 0.061(3) 0.044(3) 0.036(3) -0.007(2) -0.003(2) -0.002(2) C19 0.042(2) 0.049(3) 0.035(2) 0.006(2) 0.0092(19) 0.000(2) C20 0.030(2) 0.020(2) 0.028(2) -0.0001(17) -0.0017(17) -0.0030(16) C21 0.047(3) 0.031(3) 0.027(2) 0.0045(18) -0.007(2) -0.005(2) C22 0.037(3) 0.032(3) 0.053(3) 0.003(2) -0.018(2) -0.0011(19) C23 0.030(2) 0.041(3) 0.049(3) -0.004(2) -0.004(2) -0.0027(19) C24 0.029(2) 0.035(3) 0.032(2) 0.0050(19) 0.0019(18) -0.0023(18) C25 0.028(2) 0.029(2) 0.024(2) 0.0022(17) -0.0013(17) -0.0034(17) C26 0.029(2) 0.046(3) 0.025(2) 0.006(2) -0.0025(18) 0.0004(19) C27 0.036(2) 0.044(3) 0.029(2) -0.004(2) 0.0029(19) 0.003(2) C28 0.037(2) 0.038(3) 0.031(2) 0.002(2) -0.0067(19) -0.0019(19) C29 0.026(2) 0.036(3) 0.023(2) -0.0039(19) -0.0028(17) 0.0024(18) C30 0.039(2) 0.029(3) 0.036(2) 0.0011(19) 0.0045(19) 0.0034(18) C31 0.036(2) 0.036(3) 0.039(3) 0.009(2) 0.000(2) 0.0023(19) C32 0.026(2) 0.031(2) 0.031(2) 0.0008(18) 0.0014(17) 0.0042(17) C33 0.038(2) 0.037(3) 0.026(2) 0.003(2) 0.0050(18) -0.004(2) C34 0.037(2) 0.037(3) 0.019(2) 0.0021(18) -0.0011(17) -0.0009(19) C35 0.041(2) 0.046(3) 0.039(3) -0.011(2) 0.002(2) -0.001(2) C36 0.033(3) 0.078(4) 0.043(3) -0.012(3) -0.003(2) -0.002(2) C37 0.041(3) 0.082(4) 0.043(3) 0.009(3) -0.005(2) 0.009(3) C38 0.054(3) 0.045(3) 0.058(3) 0.018(2) -0.003(2) 0.010(2) C39 0.043(3) 0.043(3) 0.044(3) 0.008(2) -0.004(2) 0.000(2) C40 0.033(2) 0.038(3) 0.027(2) 0.0020(19) 0.0006(18) -0.0019(18) C41 0.039(2) 0.044(3) 0.031(2) 0.007(2) 0.001(2) 0.000(2) C42 0.041(2) 0.041(3) 0.024(2) 0.0026(19) 0.0024(18) 0.006(2) C43 0.062(3) 0.060(4) 0.053(3) -0.004(2) 0.009(2) 0.015(3) C44 0.063(3) 0.055(3) 0.034(3) 0.009(2) -0.003(2) 0.001(2) C45 0.035(2) 0.033(3) 0.030(2) -0.0012(19) -0.0034(18) 0.0067(18) C46 0.052(3) 0.044(3) 0.028(2) -0.001(2) -0.008(2) 0.003(2) C47 0.051(3) 0.041(3) 0.049(3) -0.003(2) -0.017(2) -0.001(2) C48 0.037(2) 0.034(3) 0.056(3) 0.002(2) -0.007(2) -0.0035(19) C49 0.043(2) 0.035(3) 0.033(2) -0.0014(19) 0.000(2) 0.004(2) C50 0.029(2) 0.037(3) 0.030(2) 0.0018(19) -0.0003(18) 0.0032(18) N1 0.048(2) 0.062(3) 0.040(3) -0.013(2) 0.0030(19) -0.003(2) N2 0.040(2) 0.065(3) 0.033(2) 0.010(2) 0.0007(18) 0.001(2) O1 0.103(3) 0.107(3) 0.043(2) 0.012(2) 0.028(2) 0.022(2) O2 0.098(3) 0.059(3) 0.088(3) -0.030(2) 0.041(2) -0.005(2) O3 0.0490(17) 0.0272(18) 0.0464(17) 0.0037(14) -0.0086(13) 0.0006(13) O4 0.0379(16) 0.048(2) 0.0407(17) -0.0004(14) 0.0030(13) 0.0131(14) O5 0.093(3) 0.069(3) 0.067(2) 0.021(2) 0.0363(19) 0.006(2) O6 0.088(2) 0.075(3) 0.041(2) -0.0187(18) 0.0209(17) -0.004(2) O7 0.0517(18) 0.036(2) 0.060(2) 0.0073(15) -0.0027(14) -0.0044(15) O8 0.0459(18) 0.087(3) 0.0401(18) 0.0090(16) 0.0005(14) -0.0195(17) _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 C1 C2 1.376(5) . ? C1 C6 1.390(5) . ? C1 N1 1.476(5) . ? C2 C3 1.390(5) . ? C2 H2 0.9500 . ? C3 C4 1.388(5) . ? C3 H3 0.9500 . ? C4 C5 1.387(5) . ? C4 C7 1.486(5) . ? C5 C6 1.382(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C15 1.340(4) . ? C7 C8 1.518(5) . ? C8 O3 1.222(4) . ? C8 C9 1.495(5) . ? C9 C10 1.386(5) . ? C9 C14 1.391(4) . ? C10 C11 1.386(4) . ? C10 H10 0.9500 . ? C11 C12 1.374(5) . ? C11 H11 0.9500 . ? C12 C13 1.385(5) . ? C12 H12 0.9500 . ? C13 C14 1.380(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C25 1.478(4) . ? C15 C16 1.498(5) . ? C16 O4 1.212(4) . ? C16 C17 1.528(5) . ? C17 C20 1.519(5) . ? C17 C19 1.535(5) . ? C17 C18 1.541(5) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.384(4) . ? C20 C25 1.404(4) . ? C21 C22 1.387(5) . ? C21 H21 0.9500 . ? C22 C23 1.377(5) . ? C22 H22 0.9500 . ? C23 C24 1.381(5) . ? C23 H23 0.9500 . ? C24 C25 1.391(5) . ? C24 H24 0.9500 . ? C26 C31 1.375(5) . ? C26 C27 1.376(5) . ? C26 N2 1.471(5) . ? C27 C28 1.382(5) . ? C27 H27 0.9500 . ? C28 C29 1.396(5) . ? C28 H28 0.9500 . ? C29 C30 1.402(5) . ? C29 C32 1.488(5) . ? C30 C31 1.385(5) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 C40 1.350(4) . ? C32 C33 1.538(5) . ? C33 O7 1.225(4) . ? C33 C34 1.489(5) . ? C34 C39 1.386(5) . ? C34 C35 1.388(5) . ? C35 C36 1.382(5) . ? C35 H35 0.9500 . ? C36 C37 1.366(6) . ? C36 H36 0.9500 . ? C37 C38 1.393(6) . ? C37 H37 0.9500 . ? C38 C39 1.377(5) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 C50 1.470(5) . ? C40 C41 1.506(5) . ? C41 O8 1.212(4) . ? C41 C42 1.532(5) . ? C42 C45 1.522(5) . ? C42 C44 1.539(5) . ? C42 C43 1.535(5) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 C46 1.379(5) . ? C45 C50 1.407(5) . ? C46 C47 1.373(5) . ? C46 H46 0.9500 . ? C47 C48 1.391(5) . ? C47 H47 0.9500 . ? C48 C49 1.388(5) . ? C48 H48 0.9500 . ? C49 C50 1.396(5) . ? C49 H49 0.9500 . ? N1 O1 1.214(4) . ? N1 O2 1.219(4) . ? N2 O5 1.225(4) . ? N2 O6 1.230(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 C2 C1 C6 122.4(4) . . ? C2 C1 N1 119.1(4) . . ? C6 C1 N1 118.5(4) . . ? C1 C2 C3 118.7(4) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 120.3(4) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.5(3) . . ? C5 C4 C7 119.4(3) . . ? C3 C4 C7 121.0(3) . . ? C6 C5 C4 121.2(4) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 117.8(4) . . ? C5 C6 H6 121.1 . . ? C1 C6 H6 121.1 . . ? C15 C7 C4 125.8(3) . . ? C15 C7 C8 122.2(3) . . ? C4 C7 C8 112.0(3) . . ? O3 C8 C9 122.9(3) . . ? O3 C8 C7 119.9(3) . . ? C9 C8 C7 116.7(3) . . ? C10 C9 C14 119.8(3) . . ? C10 C9 C8 121.8(3) . . ? C14 C9 C8 118.4(3) . . ? C9 C10 C11 120.1(3) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 119.8(4) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.5(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 120.0(3) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C9 119.8(4) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? C7 C15 C25 132.6(3) . . ? C7 C15 C16 120.9(3) . . ? C25 C15 C16 106.5(3) . . ? O4 C16 C15 126.0(3) . . ? O4 C16 C17 124.5(3) . . ? C15 C16 C17 109.5(3) . . ? C20 C17 C16 102.2(3) . . ? C20 C17 C19 112.4(3) . . ? C16 C17 C19 108.7(3) . . ? C20 C17 C18 113.0(3) . . ? C16 C17 C18 109.6(3) . . ? C19 C17 C18 110.5(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 120.1(3) . . ? C21 C20 C17 127.5(3) . . ? C25 C20 C17 112.4(3) . . ? C20 C21 C22 119.1(3) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C23 C22 C21 120.8(3) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 C24 120.8(4) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C23 C24 C25 119.2(3) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C24 C25 C20 120.0(3) . . ? C24 C25 C15 130.7(3) . . ? C20 C25 C15 109.4(3) . . ? C31 C26 C27 122.1(4) . . ? C31 C26 N2 119.7(4) . . ? C27 C26 N2 118.2(4) . . ? C28 C27 C26 118.5(4) . . ? C28 C27 H27 120.7 . . ? C26 C27 H27 120.7 . . ? C27 C28 C29 121.1(4) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C28 C29 C30 118.7(3) . . ? C28 C29 C32 119.9(4) . . ? C30 C29 C32 121.3(3) . . ? C31 C30 C29 120.2(4) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C26 C31 C30 119.3(4) . . ? C26 C31 H31 120.4 . . ? C30 C31 H31 120.4 . . ? C40 C32 C29 126.5(3) . . ? C40 C32 C33 121.6(3) . . ? C29 C32 C33 111.9(3) . . ? O7 C33 C34 123.2(3) . . ? O7 C33 C32 118.6(3) . . ? C34 C33 C32 117.7(4) . . ? C39 C34 C35 119.5(3) . . ? C39 C34 C33 121.5(3) . . ? C35 C34 C33 119.0(4) . . ? C36 C35 C34 120.0(4) . . ? C36 C35 H35 120.0 . . ? C34 C35 H35 120.0 . . ? C37 C36 C35 120.6(4) . . ? C37 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? C36 C37 C38 119.7(4) . . ? C36 C37 H37 120.1 . . ? C38 C37 H37 120.1 . . ? C39 C38 C37 120.1(4) . . ? C39 C38 H38 120.0 . . ? C37 C38 H38 120.0 . . ? C38 C39 C34 120.1(4) . . ? C38 C39 H39 119.9 . . ? C34 C39 H39 119.9 . . ? C32 C40 C50 132.7(3) . . ? C32 C40 C41 120.7(3) . . ? C50 C40 C41 106.5(3) . . ? O8 C41 C40 125.2(4) . . ? O8 C41 C42 125.3(4) . . ? C40 C41 C42 109.5(3) . . ? C45 C42 C44 112.4(3) . . ? C45 C42 C41 102.0(3) . . ? C44 C42 C41 109.1(3) . . ? C45 C42 C43 111.9(3) . . ? C44 C42 C43 110.9(3) . . ? C41 C42 C43 110.1(3) . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C42 C44 H44A 109.5 . . ? C42 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C42 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C46 C45 C50 120.7(4) . . ? C46 C45 C42 126.9(3) . . ? C50 C45 C42 112.3(3) . . ? C47 C46 C45 119.6(4) . . ? C47 C46 H46 120.2 . . ? C45 C46 H46 120.2 . . ? C46 C47 C48 120.9(4) . . ? C46 C47 H47 119.6 . . ? C48 C47 H47 119.6 . . ? C49 C48 C47 120.0(4) . . ? C49 C48 H48 120.0 . . ? C47 C48 H48 120.0 . . ? C48 C49 C50 119.7(4) . . ? C48 C49 H49 120.1 . . ? C50 C49 H49 120.1 . . ? C49 C50 C45 119.1(3) . . ? C49 C50 C40 131.3(3) . . ? C45 C50 C40 109.7(3) . . ? O1 N1 O2 124.0(4) . . ? O1 N1 C1 118.0(4) . . ? O2 N1 C1 118.0(4) . . ? O5 N2 O6 124.1(4) . . ? O5 N2 C26 117.1(4) . . ? O6 N2 C26 118.8(4) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.236 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 935873' ####################################################################### # # 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_ch15123 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H13 N O5' _chemical_formula_sum 'C22 H13 N O5' _chemical_formula_weight 371.33 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4489(8) _cell_length_b 13.8295(13) _cell_length_c 15.1615(12) _cell_angle_alpha 110.428(4) _cell_angle_beta 104.078(4) _cell_angle_gamma 100.733(4) _cell_volume 1718.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9638 _exptl_absorpt_correction_T_max 0.9949 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 14487 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.16 _reflns_number_total 6121 _reflns_number_gt 3160 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1129P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6121 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1243 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.2059 _refine_ls_wR_factor_gt 0.1340 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _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 C1 C 0.6975(4) 0.4005(3) 0.0377(3) 0.0449(9) Uani 1 1 d . . . C2 C 0.5548(4) 0.3619(3) 0.0407(3) 0.0476(9) Uani 1 1 d . . . H2 H 0.4675 0.3553 -0.0081 0.057 Uiso 1 1 calc R . . C3 C 0.5437(4) 0.3332(3) 0.1176(3) 0.0471(9) Uani 1 1 d . . . H3 H 0.4477 0.3052 0.1196 0.057 Uiso 1 1 calc R . . C4 C 0.6736(4) 0.3455(3) 0.1923(3) 0.0428(9) Uani 1 1 d . . . C5 C 0.8161(4) 0.3827(3) 0.1849(3) 0.0483(9) Uani 1 1 d . . . H5 H 0.9042 0.3889 0.2329 0.058 Uiso 1 1 calc R . . C6 C 0.8284(4) 0.4101(3) 0.1080(3) 0.0518(10) Uani 1 1 d . . . H6 H 0.9238 0.4349 0.1035 0.062 Uiso 1 1 calc R . . C7 C 0.6621(4) 0.3164(3) 0.2756(3) 0.0443(9) Uani 1 1 d . . . C8 C 0.5621(4) 0.3355(3) 0.3252(3) 0.0451(9) Uani 1 1 d . . . C9 C 0.4466(4) 0.3929(3) 0.3245(3) 0.0436(9) Uani 1 1 d . . . C10 C 0.3932(4) 0.4525(3) 0.2742(3) 0.0555(10) Uani 1 1 d . . . H10 H 0.4338 0.4634 0.2271 0.067 Uiso 1 1 calc R . . C11 C 0.2781(5) 0.4954(3) 0.2955(3) 0.0617(11) Uani 1 1 d . . . H11 H 0.2412 0.5350 0.2617 0.074 Uiso 1 1 calc R . . C12 C 0.2168(5) 0.4812(3) 0.3652(3) 0.0653(12) Uani 1 1 d . . . H12 H 0.1388 0.5106 0.3770 0.078 Uiso 1 1 calc R . . C13 C 0.2694(5) 0.4242(3) 0.4177(3) 0.0628(11) Uani 1 1 d . . . H13 H 0.2308 0.4154 0.4662 0.075 Uiso 1 1 calc R . . C14 C 0.3814(4) 0.3812(3) 0.3946(3) 0.0512(10) Uani 1 1 d . . . C15 C 0.5560(5) 0.2935(3) 0.4030(3) 0.0531(10) Uani 1 1 d . . . C16 C 0.7814(4) 0.2654(3) 0.3099(3) 0.0493(10) Uani 1 1 d . . . C17 C 0.7485(4) 0.1465(3) 0.2628(3) 0.0468(9) Uani 1 1 d . . . C18 C 0.8412(4) 0.0975(4) 0.3072(3) 0.0591(11) Uani 1 1 d . . . H18 H 0.9239 0.1396 0.3654 0.071 Uiso 1 1 calc R . . C19 C 0.8111(5) -0.0131(4) 0.2652(4) 0.0688(12) Uani 1 1 d . . . H19 H 0.8717 -0.0458 0.2961 0.083 Uiso 1 1 calc R . . C20 C 0.6925(5) -0.0750(4) 0.1782(4) 0.0701(12) Uani 1 1 d . . . H20 H 0.6733 -0.1496 0.1496 0.084 Uiso 1 1 calc R . . C21 C 0.6009(5) -0.0270(3) 0.1326(3) 0.0655(12) Uani 1 1 d . . . H21 H 0.5209 -0.0694 0.0730 0.079 Uiso 1 1 calc R . . C22 C 0.6272(4) 0.0832(3) 0.1748(3) 0.0569(10) Uani 1 1 d . . . H22 H 0.5640 0.1150 0.1446 0.068 Uiso 1 1 calc R . . C23 C 0.6293(4) 0.9042(3) 0.4352(3) 0.0481(9) Uani 1 1 d . . . C24 C 0.5350(4) 0.7999(3) 0.3881(3) 0.0540(10) Uani 1 1 d . . . H24 H 0.5627 0.7458 0.4048 0.065 Uiso 1 1 calc R . . C25 C 0.3981(4) 0.7771(3) 0.3155(3) 0.0543(10) Uani 1 1 d . . . H25 H 0.3339 0.7064 0.2819 0.065 Uiso 1 1 calc R . . C26 C 0.3540(4) 0.8579(3) 0.2915(3) 0.0434(9) Uani 1 1 d . . . C27 C 0.4538(4) 0.9623(3) 0.3401(3) 0.0467(9) Uani 1 1 d . . . H27 H 0.4275 1.0168 0.3237 0.056 Uiso 1 1 calc R . . C28 C 0.5918(4) 0.9859(3) 0.4125(3) 0.0511(10) Uani 1 1 d . . . H28 H 0.6582 1.0559 0.4453 0.061 Uiso 1 1 calc R . . C29 C 0.2074(4) 0.8302(3) 0.2116(3) 0.0432(9) Uani 1 1 d . . . C30 C 0.0712(4) 0.7702(3) 0.2032(2) 0.0414(9) Uani 1 1 d . . . C31 C 0.0139(4) 0.7283(3) 0.2681(2) 0.0407(9) Uani 1 1 d . . . C32 C 0.0758(4) 0.7279(3) 0.3616(3) 0.0500(10) Uani 1 1 d . . . H32 H 0.1802 0.7576 0.3963 0.060 Uiso 1 1 calc R . . C33 C -0.0200(5) 0.6829(3) 0.4016(3) 0.0571(11) Uani 1 1 d . . . H33 H 0.0210 0.6813 0.4632 0.069 Uiso 1 1 calc R . . C34 C -0.1746(5) 0.6405(3) 0.3526(3) 0.0635(11) Uani 1 1 d . . . H34 H -0.2367 0.6115 0.3818 0.076 Uiso 1 1 calc R . . C35 C -0.2393(5) 0.6402(3) 0.2609(3) 0.0579(11) Uani 1 1 d . . . H35 H -0.3441 0.6121 0.2272 0.070 Uiso 1 1 calc R . . C36 C -0.1425(4) 0.6831(3) 0.2220(3) 0.0459(9) Uani 1 1 d . . . C37 C -0.0661(4) 0.7387(3) 0.1140(3) 0.0484(10) Uani 1 1 d . . . C38 C 0.2257(4) 0.8659(3) 0.1294(3) 0.0481(9) Uani 1 1 d . . . C39 C 0.1949(4) 0.9668(3) 0.1305(3) 0.0411(9) Uani 1 1 d . . . C40 C 0.1555(4) 1.0339(3) 0.2062(3) 0.0494(10) Uani 1 1 d . . . H40 H 0.1436 1.0144 0.2574 0.059 Uiso 1 1 calc R . . C41 C 0.1338(4) 1.1297(3) 0.2060(3) 0.0552(10) Uani 1 1 d . . . H41 H 0.1078 1.1748 0.2572 0.066 Uiso 1 1 calc R . . C42 C 0.1503(4) 1.1586(3) 0.1308(3) 0.0554(11) Uani 1 1 d . . . H42 H 0.1355 1.2233 0.1310 0.067 Uiso 1 1 calc R . . C43 C 0.1888(4) 1.0926(3) 0.0548(3) 0.0554(11) Uani 1 1 d . . . H43 H 0.1991 1.1125 0.0036 0.066 Uiso 1 1 calc R . . C44 C 0.2118(4) 0.9977(3) 0.0544(3) 0.0487(9) Uani 1 1 d . . . H44 H 0.2389 0.9536 0.0032 0.058 Uiso 1 1 calc R . . N1 N 0.7087(5) 0.4280(3) -0.0458(2) 0.0597(9) Uani 1 1 d . . . N2 N 0.7739(4) 0.9290(3) 0.5134(3) 0.0635(9) Uani 1 1 d . . . O1 O 0.8327(4) 0.4512(3) -0.0545(2) 0.0944(11) Uani 1 1 d . . . O2 O 0.5940(4) 0.4257(3) -0.1037(2) 0.0901(11) Uani 1 1 d . . . O3 O 0.4454(3) 0.3219(2) 0.44156(19) 0.0595(7) Uani 1 1 d . . . O4 O 0.6295(3) 0.2415(2) 0.4315(2) 0.0678(8) Uani 1 1 d . . . O5 O 0.9033(3) 0.3252(2) 0.3721(2) 0.0689(8) Uani 1 1 d . . . O6 O 0.8574(4) 1.0206(3) 0.5545(3) 0.1109(14) Uani 1 1 d . . . O7 O 0.8030(4) 0.8564(3) 0.5350(3) 0.0936(11) Uani 1 1 d . . . O8 O -0.1914(3) 0.6870(2) 0.12870(18) 0.0543(7) Uani 1 1 d . . . O9 O -0.0779(3) 0.7507(2) 0.0388(2) 0.0671(8) Uani 1 1 d . . . O10 O 0.2746(3) 0.8114(2) 0.0690(2) 0.0681(8) 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 C1 0.057(3) 0.047(2) 0.034(2) 0.0221(17) 0.0161(19) 0.0145(18) C2 0.047(2) 0.053(2) 0.040(2) 0.0211(18) 0.0073(18) 0.0139(18) C3 0.040(2) 0.054(2) 0.047(2) 0.0256(19) 0.0093(18) 0.0107(18) C4 0.043(2) 0.044(2) 0.040(2) 0.0213(17) 0.0080(17) 0.0096(17) C5 0.039(2) 0.061(2) 0.045(2) 0.028(2) 0.0083(18) 0.0121(18) C6 0.045(2) 0.062(2) 0.050(2) 0.028(2) 0.0143(19) 0.0098(19) C7 0.044(2) 0.045(2) 0.039(2) 0.0208(18) 0.0056(18) 0.0048(17) C8 0.047(2) 0.044(2) 0.041(2) 0.0214(18) 0.0076(18) 0.0059(18) C9 0.045(2) 0.0385(19) 0.042(2) 0.0174(18) 0.0086(18) 0.0050(17) C10 0.054(3) 0.048(2) 0.066(3) 0.031(2) 0.016(2) 0.010(2) C11 0.061(3) 0.049(2) 0.073(3) 0.030(2) 0.015(2) 0.013(2) C12 0.050(3) 0.061(3) 0.075(3) 0.021(2) 0.017(2) 0.014(2) C13 0.057(3) 0.075(3) 0.054(3) 0.023(2) 0.022(2) 0.015(2) C14 0.049(2) 0.054(2) 0.046(2) 0.024(2) 0.0114(19) 0.0064(19) C15 0.057(3) 0.057(2) 0.044(2) 0.028(2) 0.010(2) 0.012(2) C16 0.041(2) 0.067(3) 0.044(2) 0.035(2) 0.0094(19) 0.010(2) C17 0.038(2) 0.061(2) 0.046(2) 0.029(2) 0.0122(19) 0.0156(19) C18 0.047(2) 0.083(3) 0.061(3) 0.039(2) 0.020(2) 0.026(2) C19 0.070(3) 0.079(3) 0.084(4) 0.047(3) 0.037(3) 0.042(3) C20 0.071(3) 0.066(3) 0.082(3) 0.028(3) 0.036(3) 0.030(3) C21 0.061(3) 0.064(3) 0.061(3) 0.017(2) 0.020(2) 0.013(2) C22 0.051(2) 0.065(3) 0.055(3) 0.030(2) 0.015(2) 0.015(2) C23 0.043(2) 0.063(3) 0.042(2) 0.024(2) 0.0141(18) 0.020(2) C24 0.049(2) 0.061(3) 0.065(3) 0.038(2) 0.017(2) 0.025(2) C25 0.050(2) 0.045(2) 0.068(3) 0.031(2) 0.009(2) 0.0137(18) C26 0.040(2) 0.051(2) 0.044(2) 0.0236(18) 0.0154(18) 0.0139(18) C27 0.049(2) 0.045(2) 0.048(2) 0.0247(18) 0.0125(19) 0.0132(18) C28 0.049(2) 0.050(2) 0.046(2) 0.0172(19) 0.012(2) 0.0077(19) C29 0.049(2) 0.040(2) 0.044(2) 0.0215(17) 0.0139(18) 0.0138(17) C30 0.045(2) 0.0397(19) 0.039(2) 0.0195(17) 0.0110(17) 0.0112(17) C31 0.044(2) 0.0385(19) 0.038(2) 0.0174(16) 0.0086(17) 0.0115(17) C32 0.050(2) 0.053(2) 0.040(2) 0.0202(19) 0.0054(19) 0.0113(19) C33 0.075(3) 0.065(3) 0.043(2) 0.032(2) 0.023(2) 0.025(2) C34 0.067(3) 0.073(3) 0.060(3) 0.036(2) 0.028(2) 0.019(2) C35 0.048(2) 0.068(3) 0.063(3) 0.034(2) 0.018(2) 0.014(2) C36 0.047(2) 0.048(2) 0.044(2) 0.0251(19) 0.0093(19) 0.0151(18) C37 0.051(2) 0.047(2) 0.046(2) 0.0261(19) 0.0069(19) 0.0113(18) C38 0.051(2) 0.047(2) 0.045(2) 0.023(2) 0.0123(19) 0.0100(19) C39 0.039(2) 0.046(2) 0.041(2) 0.0231(18) 0.0123(17) 0.0097(17) C40 0.056(2) 0.055(2) 0.045(2) 0.028(2) 0.0198(19) 0.0153(19) C41 0.061(3) 0.049(2) 0.061(3) 0.025(2) 0.022(2) 0.020(2) C42 0.052(2) 0.048(2) 0.070(3) 0.036(2) 0.012(2) 0.011(2) C43 0.050(2) 0.069(3) 0.056(3) 0.042(2) 0.013(2) 0.014(2) C44 0.046(2) 0.062(2) 0.041(2) 0.0256(19) 0.0138(18) 0.0145(19) N1 0.065(2) 0.071(2) 0.050(2) 0.0334(19) 0.020(2) 0.016(2) N2 0.052(2) 0.077(3) 0.052(2) 0.019(2) 0.0076(18) 0.025(2) O1 0.076(2) 0.142(3) 0.087(2) 0.077(2) 0.034(2) 0.015(2) O2 0.077(2) 0.148(3) 0.065(2) 0.070(2) 0.0160(18) 0.038(2) O3 0.0608(18) 0.0763(19) 0.0546(17) 0.0397(15) 0.0237(15) 0.0190(15) O4 0.085(2) 0.0778(19) 0.0625(19) 0.0473(17) 0.0281(16) 0.0339(17) O5 0.0500(17) 0.0787(19) 0.0655(19) 0.0410(16) -0.0045(15) 0.0009(15) O6 0.077(2) 0.077(2) 0.117(3) 0.019(2) -0.031(2) 0.010(2) O7 0.074(2) 0.106(3) 0.098(3) 0.054(2) -0.0010(19) 0.037(2) O8 0.0449(15) 0.0615(16) 0.0515(16) 0.0315(14) 0.0034(12) 0.0056(13) O9 0.073(2) 0.0768(19) 0.0496(17) 0.0406(15) 0.0053(15) 0.0106(15) O10 0.095(2) 0.0607(17) 0.0660(19) 0.0284(15) 0.0442(18) 0.0341(17) _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 C1 C6 1.372(5) . ? C1 C2 1.373(5) . ? C1 N1 1.463(4) . ? C2 C3 1.376(5) . ? C2 H2 0.9300 . ? C3 C4 1.389(5) . ? C3 H3 0.9300 . ? C4 C5 1.395(5) . ? C4 C7 1.475(5) . ? C5 C6 1.370(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.353(5) . ? C7 C16 1.519(5) . ? C8 C9 1.465(5) . ? C8 C15 1.493(5) . ? C9 C14 1.391(5) . ? C9 C10 1.387(5) . ? C10 C11 1.384(5) . ? C10 H10 0.9300 . ? C11 C12 1.376(6) . ? C11 H11 0.9300 . ? C12 C13 1.375(5) . ? C12 H12 0.9300 . ? C13 C14 1.366(5) . ? C13 H13 0.9300 . ? C14 O3 1.389(4) . ? C15 O4 1.202(4) . ? C15 O3 1.370(5) . ? C16 O5 1.214(4) . ? C16 C17 1.480(5) . ? C17 C18 1.389(5) . ? C17 C22 1.389(5) . ? C18 C19 1.378(6) . ? C18 H18 0.9300 . ? C19 C20 1.364(6) . ? C19 H19 0.9300 . ? C20 C21 1.383(6) . ? C20 H20 0.9300 . ? C21 C22 1.376(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.370(5) . ? C23 C28 1.370(5) . ? C23 N2 1.464(5) . ? C24 C25 1.377(5) . ? C24 H24 0.9300 . ? C25 C26 1.392(5) . ? C25 H25 0.9300 . ? C26 C27 1.388(5) . ? C26 C29 1.482(5) . ? C27 C28 1.381(5) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.345(5) . ? C29 C38 1.525(5) . ? C30 C31 1.463(5) . ? C30 C37 1.491(5) . ? C31 C36 1.383(5) . ? C31 C32 1.398(4) . ? C32 C33 1.376(5) . ? C32 H32 0.9300 . ? C33 C34 1.370(5) . ? C33 H33 0.9300 . ? C34 C35 1.374(5) . ? C34 H34 0.9300 . ? C35 C36 1.357(5) . ? C35 H35 0.9300 . ? C36 O8 1.400(4) . ? C37 O9 1.190(4) . ? C37 O8 1.374(4) . ? C38 O10 1.214(4) . ? C38 C39 1.473(5) . ? C39 C40 1.382(5) . ? C39 C44 1.396(4) . ? C40 C41 1.380(5) . ? C40 H40 0.9300 . ? C41 C42 1.365(5) . ? C41 H41 0.9300 . ? C42 C43 1.373(5) . ? C42 H42 0.9300 . ? C43 C44 1.368(5) . ? C43 H43 0.9300 . ? C44 H44 0.9300 . ? N1 O2 1.205(4) . ? N1 O1 1.208(4) . ? N2 O6 1.205(4) . ? N2 O7 1.217(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 C1 C2 122.1(3) . . ? C6 C1 N1 119.5(3) . . ? C2 C1 N1 118.4(3) . . ? C1 C2 C3 118.6(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 121.0(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 118.3(3) . . ? C3 C4 C7 121.2(3) . . ? C5 C4 C7 120.4(3) . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 118.8(3) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? C8 C7 C4 126.3(3) . . ? C8 C7 C16 118.8(3) . . ? C4 C7 C16 114.8(3) . . ? C7 C8 C9 135.6(3) . . ? C7 C8 C15 120.2(3) . . ? C9 C8 C15 104.2(3) . . ? C14 C9 C10 117.4(4) . . ? C14 C9 C8 106.4(3) . . ? C10 C9 C8 136.2(3) . . ? C11 C10 C9 118.5(4) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C12 C11 C10 122.0(4) . . ? C12 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C11 C12 C13 120.8(4) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 116.3(4) . . ? C14 C13 H13 121.8 . . ? C12 C13 H13 121.8 . . ? C13 C14 C9 125.0(4) . . ? C13 C14 O3 122.6(4) . . ? C9 C14 O3 112.4(3) . . ? O4 C15 O3 121.1(3) . . ? O4 C15 C8 129.6(4) . . ? O3 C15 C8 109.3(3) . . ? O5 C16 C17 122.8(3) . . ? O5 C16 C7 117.8(3) . . ? C17 C16 C7 119.3(3) . . ? C18 C17 C22 119.4(4) . . ? C18 C17 C16 119.4(3) . . ? C22 C17 C16 121.2(3) . . ? C19 C18 C17 120.2(4) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 120.1(4) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 120.1(4) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 120.5(4) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C17 119.6(4) . . ? C21 C22 H22 120.2 . . ? C17 C22 H22 120.2 . . ? C24 C23 C28 122.3(3) . . ? C24 C23 N2 118.5(3) . . ? C28 C23 N2 119.2(4) . . ? C23 C24 C25 118.4(3) . . ? C23 C24 H24 120.8 . . ? C25 C24 H24 120.8 . . ? C24 C25 C26 121.3(3) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C27 C26 C25 118.5(3) . . ? C27 C26 C29 121.6(3) . . ? C25 C26 C29 119.9(3) . . ? C28 C27 C26 120.7(3) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C23 C28 C27 118.8(3) . . ? C23 C28 H28 120.6 . . ? C27 C28 H28 120.6 . . ? C30 C29 C26 125.5(3) . . ? C30 C29 C38 120.8(3) . . ? C26 C29 C38 113.3(3) . . ? C29 C30 C31 134.6(3) . . ? C29 C30 C37 120.7(3) . . ? C31 C30 C37 104.6(3) . . ? C36 C31 C32 116.7(3) . . ? C36 C31 C30 106.8(3) . . ? C32 C31 C30 136.4(3) . . ? C33 C32 C31 119.1(4) . . ? C33 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? C34 C33 C32 121.4(4) . . ? C34 C33 H33 119.3 . . ? C32 C33 H33 119.3 . . ? C33 C34 C35 121.0(4) . . ? C33 C34 H34 119.5 . . ? C35 C34 H34 119.5 . . ? C36 C35 C34 116.6(4) . . ? C36 C35 H35 121.7 . . ? C34 C35 H35 121.7 . . ? C35 C36 C31 125.1(3) . . ? C35 C36 O8 123.1(3) . . ? C31 C36 O8 111.8(3) . . ? O9 C37 O8 120.8(3) . . ? O9 C37 C30 130.5(4) . . ? O8 C37 C30 108.7(3) . . ? O10 C38 C39 123.2(3) . . ? O10 C38 C29 116.9(3) . . ? C39 C38 C29 119.7(3) . . ? C40 C39 C44 118.9(3) . . ? C40 C39 C38 122.3(3) . . ? C44 C39 C38 118.8(3) . . ? C41 C40 C39 120.1(3) . . ? C41 C40 H40 119.9 . . ? C39 C40 H40 119.9 . . ? C42 C41 C40 120.2(4) . . ? C42 C41 H41 119.9 . . ? C40 C41 H41 119.9 . . ? C41 C42 C43 120.4(4) . . ? C41 C42 H42 119.8 . . ? C43 C42 H42 119.8 . . ? C44 C43 C42 120.1(4) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C43 C44 C39 120.3(4) . . ? C43 C44 H44 119.9 . . ? C39 C44 H44 119.9 . . ? O2 N1 O1 122.4(3) . . ? O2 N1 C1 119.0(4) . . ? O1 N1 C1 118.6(3) . . ? O6 N2 O7 123.0(4) . . ? O6 N2 C23 118.6(4) . . ? O7 N2 C23 118.4(4) . . ? C15 O3 C14 107.7(3) . . ? C37 O8 C36 108.0(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.16 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.272 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 937197' ####################################################################### # # 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_ch14805 #TrackingRef 'ch14805.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H13 Br N2 O' _chemical_formula_sum 'C23 H13 Br N2 O' _chemical_formula_weight 413.26 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' Br Br -0.2901 2.4595 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1664(9) _cell_length_b 11.6963(11) _cell_length_c 17.6206(15) _cell_angle_alpha 92.092(2) _cell_angle_beta 106.720(2) _cell_angle_gamma 114.912(2) _cell_volume 1789.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 2.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4435 _exptl_absorpt_correction_T_max 0.7851 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 14808 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _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 1.23 _diffrn_reflns_theta_max 25.08 _reflns_number_total 6279 _reflns_number_gt 4613 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0794P)^2^+0.5644P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6279 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0664(5) 0.6504(4) 1.1045(3) 0.0279(10) Uani 1 1 d . . . C2 C 1.1177(5) 0.6456(4) 1.0404(3) 0.0284(10) Uani 1 1 d . . . H2 H 1.1776 0.6017 1.0398 0.034 Uiso 1 1 calc R . . C3 C 1.0805(5) 0.7061(4) 0.9766(3) 0.0268(10) Uani 1 1 d . . . H3 H 1.1154 0.7029 0.9324 0.032 Uiso 1 1 calc R . . C4 C 0.9931(5) 0.7712(4) 0.9768(2) 0.0254(10) Uani 1 1 d . . . C5 C 0.9427(5) 0.7745(4) 1.0426(2) 0.0298(10) Uani 1 1 d . . . H5 H 0.8817 0.8174 1.0434 0.036 Uiso 1 1 calc R . . C6 C 0.9808(5) 0.7158(4) 1.1064(3) 0.0314(11) Uani 1 1 d . . . H6 H 0.9484 0.7204 1.1514 0.038 Uiso 1 1 calc R . . C7 C 0.9607(5) 0.8383(4) 0.9099(2) 0.0214(9) Uani 1 1 d . . . C8 C 0.8077(5) 0.8249(4) 0.8676(2) 0.0266(10) Uani 1 1 d . . . C9 C 0.6693(5) 0.7405(4) 0.8874(2) 0.0271(10) Uani 1 1 d . . . C10 C 0.6266(5) 0.6110(4) 0.8894(2) 0.0288(10) Uani 1 1 d . . . H10 H 0.6886 0.5739 0.8795 0.035 Uiso 1 1 calc R . . C11 C 0.4943(6) 0.5366(5) 0.9057(3) 0.0400(12) Uani 1 1 d . . . H11 H 0.4666 0.4487 0.9074 0.048 Uiso 1 1 calc R . . C12 C 0.3990(6) 0.5888(5) 0.9201(3) 0.0477(15) Uani 1 1 d . . . H12 H 0.3059 0.5366 0.9292 0.057 Uiso 1 1 calc R . . C13 C 0.4453(6) 0.7164(6) 0.9203(3) 0.0448(13) Uani 1 1 d . . . H13 H 0.3854 0.7540 0.9324 0.054 Uiso 1 1 calc R . . C14 C 0.5776(5) 0.7938(5) 0.9034(3) 0.0341(11) Uani 1 1 d . . . H14 H 0.6055 0.8820 0.9027 0.041 Uiso 1 1 calc R . . C15 C 1.0334(5) 0.9869(4) 0.8216(2) 0.0247(10) Uani 1 1 d . . . C16 C 1.0722(5) 0.9225(4) 0.8829(2) 0.0237(9) Uani 1 1 d . . . C17 C 1.2464(5) 0.9731(4) 0.9116(3) 0.0291(10) Uani 1 1 d . . . C18 C 1.3005(5) 1.0729(4) 0.8620(3) 0.0297(10) Uani 1 1 d . . . C19 C 1.1750(5) 1.0807(4) 0.8086(3) 0.0271(10) Uani 1 1 d . . . C20 C 1.1950(6) 1.1657(5) 0.7556(3) 0.0351(11) Uani 1 1 d . . . H20 H 1.1097 1.1706 0.7184 0.042 Uiso 1 1 calc R . . C21 C 1.3468(6) 1.2448(5) 0.7589(3) 0.0410(13) Uani 1 1 d . . . H21 H 1.3649 1.3057 0.7242 0.049 Uiso 1 1 calc R . . C22 C 1.4711(6) 1.2349(5) 0.8126(3) 0.0422(13) Uani 1 1 d . . . H22 H 1.5725 1.2885 0.8133 0.051 Uiso 1 1 calc R . . C23 C 1.4492(5) 1.1489(5) 0.8643(3) 0.0372(12) Uani 1 1 d . . . H23 H 1.5339 1.1419 0.9006 0.045 Uiso 1 1 calc R . . C24 C 0.6455(5) 0.1675(4) 0.5917(3) 0.0293(10) Uani 1 1 d . . . C25 C 0.6503(5) 0.1562(4) 0.5138(2) 0.0278(10) Uani 1 1 d . . . H25 H 0.7068 0.1162 0.5003 0.033 Uiso 1 1 calc R . . C26 C 0.5729(5) 0.2031(4) 0.4566(2) 0.0274(10) Uani 1 1 d . . . H26 H 0.5797 0.1981 0.4040 0.033 Uiso 1 1 calc R . . C27 C 0.4845(5) 0.2579(4) 0.4742(2) 0.0264(10) Uani 1 1 d . . . C28 C 0.4815(5) 0.2686(5) 0.5526(3) 0.0331(11) Uani 1 1 d . . . H28 H 0.4234 0.3071 0.5659 0.040 Uiso 1 1 calc R . . C29 C 0.5615(5) 0.2243(4) 0.6113(3) 0.0318(11) Uani 1 1 d . . . H29 H 0.5589 0.2327 0.6647 0.038 Uiso 1 1 calc R . . C30 C 0.3943(5) 0.3014(4) 0.4124(2) 0.0255(10) Uani 1 1 d . . . C31 C 0.4612(5) 0.3981(4) 0.3673(2) 0.0277(10) Uani 1 1 d . . . C32 C 0.6288(5) 0.4622(4) 0.3792(3) 0.0299(10) Uani 1 1 d . . . C33 C 0.7397(6) 0.5170(5) 0.4556(3) 0.0375(12) Uani 1 1 d . . . H33 H 0.7097 0.5098 0.5022 0.045 Uiso 1 1 calc R . . C34 C 0.8938(6) 0.5820(5) 0.4631(3) 0.0476(14) Uani 1 1 d . . . H34 H 0.9687 0.6192 0.5152 0.057 Uiso 1 1 calc R . . C35 C 0.9425(6) 0.5944(5) 0.3944(4) 0.0558(16) Uani 1 1 d . . . H35 H 1.0478 0.6418 0.3994 0.067 Uiso 1 1 calc R . . C36 C 0.8321(6) 0.5356(5) 0.3218(3) 0.0493(14) Uani 1 1 d . . . H36 H 0.8622 0.5387 0.2753 0.059 Uiso 1 1 calc R . . C37 C 0.6755(5) 0.4703(5) 0.3121(3) 0.0372(12) Uani 1 1 d . . . H37 H 0.6015 0.4317 0.2599 0.045 Uiso 1 1 calc R . . C38 C 0.1575(5) 0.3019(4) 0.3325(2) 0.0256(10) Uani 1 1 d . . . C39 C 0.2379(5) 0.2542(4) 0.3918(2) 0.0260(10) Uani 1 1 d . . . C40 C 0.1186(5) 0.1474(4) 0.4169(3) 0.0292(10) Uani 1 1 d . . . C41 C -0.0315(5) 0.1434(4) 0.3704(3) 0.0273(10) Uani 1 1 d . . . C42 C -0.0088(5) 0.2348(4) 0.3204(2) 0.0263(10) Uani 1 1 d . . . C43 C -0.1319(5) 0.2495(5) 0.2708(3) 0.0330(11) Uani 1 1 d . . . H43 H -0.1168 0.3118 0.2369 0.040 Uiso 1 1 calc R . . C44 C -0.2787(5) 0.1696(5) 0.2723(3) 0.0353(11) Uani 1 1 d . . . H44 H -0.3648 0.1782 0.2390 0.042 Uiso 1 1 calc R . . C45 C -0.3015(5) 0.0777(5) 0.3217(3) 0.0352(11) Uani 1 1 d . . . H45 H -0.4026 0.0245 0.3215 0.042 Uiso 1 1 calc R . . C46 C -0.1785(5) 0.0630(4) 0.3712(3) 0.0327(11) Uani 1 1 d . . . H46 H -0.1938 0.0001 0.4046 0.039 Uiso 1 1 calc R . . N1 N 0.7783(4) 0.8877(4) 0.8080(2) 0.0319(9) Uani 1 1 d . . . N2 N 0.8928(4) 0.9720(4) 0.7845(2) 0.0306(9) Uani 1 1 d . . . N3 N 0.3782(4) 0.4393(4) 0.3112(2) 0.0344(10) Uani 1 1 d . . . N4 N 0.2238(4) 0.3911(4) 0.2933(2) 0.0316(9) Uani 1 1 d . . . O1 O 1.3245(3) 0.9427(3) 0.9637(2) 0.0445(9) Uani 1 1 d . . . O2 O 0.1416(4) 0.0779(4) 0.4628(2) 0.0470(9) Uani 1 1 d . . . Br1 Br 1.11262(5) 0.56192(5) 1.18857(3) 0.03409(16) Uani 1 1 d . . . Br2 Br 0.74888(5) 0.10040(5) 0.67035(3) 0.03507(16) 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 C1 0.029(2) 0.027(3) 0.023(2) 0.0102(19) 0.0044(19) 0.011(2) C2 0.028(2) 0.025(3) 0.035(2) 0.011(2) 0.009(2) 0.015(2) C3 0.030(2) 0.027(3) 0.029(2) 0.0110(19) 0.013(2) 0.016(2) C4 0.024(2) 0.024(2) 0.024(2) 0.0059(18) 0.0044(19) 0.0104(19) C5 0.032(3) 0.035(3) 0.027(2) 0.004(2) 0.010(2) 0.019(2) C6 0.040(3) 0.034(3) 0.024(2) 0.006(2) 0.010(2) 0.021(2) C7 0.026(2) 0.019(2) 0.019(2) 0.0015(17) 0.0060(18) 0.0104(19) C8 0.033(2) 0.026(3) 0.025(2) 0.0069(19) 0.008(2) 0.018(2) C9 0.026(2) 0.033(3) 0.022(2) 0.0091(19) 0.0061(19) 0.014(2) C10 0.030(2) 0.030(3) 0.025(2) 0.0055(19) 0.0048(19) 0.015(2) C11 0.047(3) 0.038(3) 0.030(3) 0.012(2) 0.013(2) 0.015(3) C12 0.059(4) 0.037(3) 0.036(3) 0.009(2) 0.029(3) 0.003(3) C13 0.039(3) 0.068(4) 0.039(3) 0.014(3) 0.018(2) 0.032(3) C14 0.037(3) 0.034(3) 0.034(3) 0.008(2) 0.012(2) 0.019(2) C15 0.032(2) 0.026(2) 0.019(2) 0.0041(18) 0.0081(19) 0.015(2) C16 0.026(2) 0.020(2) 0.023(2) -0.0007(18) 0.0039(18) 0.0106(19) C17 0.025(2) 0.024(3) 0.032(2) 0.004(2) 0.004(2) 0.010(2) C18 0.031(3) 0.025(3) 0.030(2) 0.001(2) 0.009(2) 0.010(2) C19 0.037(3) 0.023(2) 0.027(2) 0.0064(19) 0.018(2) 0.014(2) C20 0.048(3) 0.032(3) 0.035(3) 0.011(2) 0.021(2) 0.022(2) C21 0.057(3) 0.029(3) 0.047(3) 0.013(2) 0.034(3) 0.018(3) C22 0.038(3) 0.034(3) 0.052(3) 0.008(2) 0.025(3) 0.007(2) C23 0.035(3) 0.034(3) 0.039(3) 0.001(2) 0.013(2) 0.012(2) C24 0.027(2) 0.022(2) 0.033(2) 0.013(2) 0.005(2) 0.009(2) C25 0.031(2) 0.027(3) 0.031(2) 0.008(2) 0.013(2) 0.016(2) C26 0.035(3) 0.031(3) 0.022(2) 0.0058(19) 0.013(2) 0.017(2) C27 0.030(2) 0.027(2) 0.023(2) 0.0059(18) 0.0096(19) 0.013(2) C28 0.038(3) 0.041(3) 0.030(2) 0.010(2) 0.012(2) 0.026(2) C29 0.039(3) 0.040(3) 0.022(2) 0.007(2) 0.011(2) 0.023(2) C30 0.033(2) 0.027(3) 0.019(2) 0.0026(18) 0.0078(19) 0.017(2) C31 0.035(3) 0.028(3) 0.022(2) 0.0079(19) 0.007(2) 0.017(2) C32 0.033(3) 0.021(2) 0.037(3) 0.012(2) 0.010(2) 0.015(2) C33 0.042(3) 0.031(3) 0.033(3) 0.000(2) 0.007(2) 0.015(2) C34 0.036(3) 0.036(3) 0.056(3) 0.000(3) 0.000(3) 0.013(3) C35 0.025(3) 0.042(3) 0.078(4) -0.017(3) -0.005(3) 0.012(3) C36 0.048(3) 0.048(3) 0.065(4) 0.028(3) 0.031(3) 0.023(3) C37 0.035(3) 0.041(3) 0.037(3) 0.019(2) 0.013(2) 0.017(2) C38 0.030(2) 0.026(2) 0.020(2) 0.0048(18) 0.0072(19) 0.013(2) C39 0.033(2) 0.029(3) 0.020(2) 0.0068(18) 0.0086(19) 0.018(2) C40 0.032(2) 0.036(3) 0.026(2) 0.014(2) 0.014(2) 0.018(2) C41 0.034(2) 0.031(3) 0.026(2) 0.0085(19) 0.014(2) 0.019(2) C42 0.031(2) 0.028(3) 0.021(2) 0.0031(18) 0.0084(19) 0.016(2) C43 0.037(3) 0.042(3) 0.026(2) 0.010(2) 0.006(2) 0.025(2) C44 0.029(3) 0.042(3) 0.037(3) 0.005(2) 0.006(2) 0.021(2) C45 0.035(3) 0.041(3) 0.033(3) 0.005(2) 0.018(2) 0.017(2) C46 0.040(3) 0.033(3) 0.033(3) 0.010(2) 0.020(2) 0.019(2) N1 0.033(2) 0.037(2) 0.031(2) 0.0158(18) 0.0118(17) 0.0193(19) N2 0.034(2) 0.033(2) 0.027(2) 0.0146(17) 0.0120(17) 0.0155(19) N3 0.033(2) 0.037(2) 0.032(2) 0.0137(18) 0.0062(18) 0.0159(19) N4 0.027(2) 0.032(2) 0.036(2) 0.0159(18) 0.0082(17) 0.0142(18) O1 0.0239(17) 0.042(2) 0.054(2) 0.0193(17) -0.0009(16) 0.0106(16) O2 0.043(2) 0.058(2) 0.053(2) 0.0405(19) 0.0246(18) 0.0266(19) Br1 0.0352(3) 0.0358(3) 0.0300(3) 0.0167(2) 0.0091(2) 0.0151(2) Br2 0.0333(3) 0.0378(3) 0.0332(3) 0.0147(2) 0.0046(2) 0.0188(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 C1 C6 1.386(6) . ? C1 C2 1.381(6) . ? C1 Br1 1.899(4) . ? C2 C3 1.395(6) . ? C2 H2 0.9500 . ? C3 C4 1.392(6) . ? C3 H3 0.9500 . ? C4 C5 1.402(6) . ? C4 C7 1.475(6) . ? C5 C6 1.384(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C16 1.373(6) . ? C7 C8 1.456(6) . ? C8 N1 1.339(5) . ? C8 C9 1.487(6) . ? C9 C10 1.394(6) . ? C9 C14 1.402(6) . ? C10 C11 1.381(6) . ? C10 H10 0.9500 . ? C11 C12 1.415(7) . ? C11 H11 0.9500 . ? C12 C13 1.363(7) . ? C12 H12 0.9500 . ? C13 C14 1.394(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N2 1.320(5) . ? C15 C16 1.398(6) . ? C15 C19 1.485(6) . ? C16 C17 1.524(6) . ? C17 O1 1.200(5) . ? C17 C18 1.496(6) . ? C18 C23 1.381(6) . ? C18 C19 1.392(6) . ? C19 C20 1.381(6) . ? C20 C21 1.409(7) . ? C20 H20 0.9500 . ? C21 C22 1.395(7) . ? C21 H21 0.9500 . ? C22 C23 1.374(7) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C29 1.387(6) . ? C24 C25 1.391(6) . ? C24 Br2 1.892(4) . ? C25 C26 1.372(6) . ? C25 H25 0.9500 . ? C26 C27 1.396(6) . ? C26 H26 0.9500 . ? C27 C28 1.392(6) . ? C27 C30 1.465(6) . ? C28 C29 1.383(6) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C39 1.371(6) . ? C30 C31 1.449(6) . ? C31 N3 1.349(5) . ? C31 C32 1.489(6) . ? C32 C37 1.388(6) . ? C32 C33 1.396(6) . ? C33 C34 1.386(7) . ? C33 H33 0.9500 . ? C34 C35 1.424(8) . ? C34 H34 0.9500 . ? C35 C36 1.353(7) . ? C35 H35 0.9500 . ? C36 C37 1.398(7) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 N4 1.322(5) . ? C38 C39 1.417(6) . ? C38 C42 1.477(6) . ? C39 C40 1.517(6) . ? C40 O2 1.211(5) . ? C40 C41 1.490(6) . ? C41 C42 1.396(6) . ? C41 C46 1.395(6) . ? C42 C43 1.386(6) . ? C43 C44 1.397(6) . ? C43 H43 0.9500 . ? C44 C45 1.393(7) . ? C44 H44 0.9500 . ? C45 C46 1.384(6) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? N1 N2 1.356(5) . ? N3 N4 1.356(5) . ? 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 C1 C2 120.8(4) . . ? C6 C1 Br1 121.0(3) . . ? C2 C1 Br1 118.2(3) . . ? C1 C2 C3 119.2(4) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 121.0(4) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 118.5(4) . . ? C3 C4 C7 119.7(4) . . ? C5 C4 C7 121.8(4) . . ? C6 C5 C4 120.6(4) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 119.8(4) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C16 C7 C8 113.2(4) . . ? C16 C7 C4 123.5(4) . . ? C8 C7 C4 123.2(4) . . ? N1 C8 C7 123.4(4) . . ? N1 C8 C9 113.8(4) . . ? C7 C8 C9 122.8(4) . . ? C10 C9 C14 119.1(4) . . ? C10 C9 C8 122.6(4) . . ? C14 C9 C8 118.2(4) . . ? C11 C10 C9 119.9(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 121.4(5) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C12 C11 117.7(5) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C12 C13 C14 122.2(5) . . ? C12 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? C13 C14 C9 119.5(5) . . ? C13 C14 H14 120.2 . . ? C9 C14 H14 120.2 . . ? N2 C15 C16 124.9(4) . . ? N2 C15 C19 125.2(4) . . ? C16 C15 C19 109.8(4) . . ? C7 C16 C15 120.1(4) . . ? C7 C16 C17 132.1(4) . . ? C15 C16 C17 107.6(4) . . ? O1 C17 C18 127.1(4) . . ? O1 C17 C16 128.1(4) . . ? C18 C17 C16 104.7(4) . . ? C23 C18 C19 121.8(4) . . ? C23 C18 C17 128.4(4) . . ? C19 C18 C17 109.8(4) . . ? C20 C19 C18 120.9(4) . . ? C20 C19 C15 131.0(4) . . ? C18 C19 C15 108.1(4) . . ? C19 C20 C21 117.4(5) . . ? C19 C20 H20 121.3 . . ? C21 C20 H20 121.3 . . ? C22 C21 C20 120.9(5) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C23 C22 C21 121.1(5) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C18 118.0(5) . . ? C22 C23 H23 121.0 . . ? C18 C23 H23 121.0 . . ? C29 C24 C25 120.3(4) . . ? C29 C24 Br2 119.8(3) . . ? C25 C24 Br2 119.9(3) . . ? C26 C25 C24 119.7(4) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C27 121.2(4) . . ? C25 C26 H26 119.4 . . ? C27 C26 H26 119.4 . . ? C28 C27 C26 118.3(4) . . ? C28 C27 C30 120.1(4) . . ? C26 C27 C30 121.6(4) . . ? C29 C28 C27 121.2(4) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C28 C29 C24 119.3(4) . . ? C28 C29 H29 120.3 . . ? C24 C29 H29 120.3 . . ? C39 C30 C31 113.6(4) . . ? C39 C30 C27 122.9(4) . . ? C31 C30 C27 123.5(4) . . ? N3 C31 C30 123.4(4) . . ? N3 C31 C32 113.6(4) . . ? C30 C31 C32 123.0(4) . . ? C37 C32 C33 119.2(4) . . ? C37 C32 C31 118.9(4) . . ? C33 C32 C31 121.9(4) . . ? C34 C33 C32 119.6(5) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 C35 121.5(5) . . ? C33 C34 H34 119.2 . . ? C35 C34 H34 119.2 . . ? C36 C35 C34 116.9(5) . . ? C36 C35 H35 121.5 . . ? C34 C35 H35 121.5 . . ? C35 C36 C37 122.9(5) . . ? C35 C36 H36 118.6 . . ? C37 C36 H36 118.6 . . ? C32 C37 C36 119.7(5) . . ? C32 C37 H37 120.2 . . ? C36 C37 H37 120.2 . . ? N4 C38 C39 124.0(4) . . ? N4 C38 C42 126.2(4) . . ? C39 C38 C42 109.8(4) . . ? C30 C39 C38 120.2(4) . . ? C30 C39 C40 132.6(4) . . ? C38 C39 C40 107.1(4) . . ? O2 C40 C41 128.0(4) . . ? O2 C40 C39 126.8(4) . . ? C41 C40 C39 105.1(4) . . ? C42 C41 C46 121.1(4) . . ? C42 C41 C40 110.0(4) . . ? C46 C41 C40 128.9(4) . . ? C43 C42 C41 120.8(4) . . ? C43 C42 C38 131.2(4) . . ? C41 C42 C38 107.9(4) . . ? C42 C43 C44 117.8(4) . . ? C42 C43 H43 121.1 . . ? C44 C43 H43 121.1 . . ? C45 C44 C43 121.3(4) . . ? C45 C44 H44 119.3 . . ? C43 C44 H44 119.3 . . ? C46 C45 C44 120.8(4) . . ? C46 C45 H45 119.6 . . ? C44 C45 H45 119.6 . . ? C45 C46 C41 118.1(4) . . ? C45 C46 H46 121.0 . . ? C41 C46 H46 121.0 . . ? C8 N1 N2 121.2(4) . . ? C15 N2 N1 117.1(4) . . ? C31 N3 N4 121.0(4) . . ? C38 N4 N3 117.7(4) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.093 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.132 _database_code_depnum_ccdc_archive 'CCDC 935874' ####################################################################### # # 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_a14911 #TrackingRef 'a14911.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H15 N3 O2' _chemical_formula_sum 'C26 H15 N3 O2' _chemical_formula_weight 401.41 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1355(10) _cell_length_b 9.9649(11) _cell_length_c 12.9125(16) _cell_angle_alpha 70.085(7) _cell_angle_beta 83.705(9) _cell_angle_gamma 84.108(8) _cell_volume 975.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9705 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 7836 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0914 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3398 _reflns_number_gt 1982 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0964P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3398 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1219 _refine_ls_R_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.1983 _refine_ls_wR_factor_gt 0.1692 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 C1 C 0.2874(4) 0.9761(3) 0.6330(3) 0.0358(8) Uani 1 1 d . . . C2 C 0.4138(4) 0.9550(4) 0.7016(3) 0.0381(9) Uani 1 1 d . . . H2 H 0.5055 1.0131 0.6796 0.046 Uiso 1 1 calc R . . C3 C 0.4031(4) 0.8472(3) 0.8028(3) 0.0373(9) Uani 1 1 d . . . H3 H 0.4889 0.8303 0.8511 0.045 Uiso 1 1 calc R . . C4 C 0.2684(4) 0.7632(3) 0.8348(3) 0.0322(8) Uani 1 1 d . . . C5 C 0.1419(4) 0.7890(3) 0.7647(3) 0.0378(9) Uani 1 1 d . . . H5 H 0.0487 0.7327 0.7870 0.045 Uiso 1 1 calc R . . C6 C 0.1508(4) 0.8960(4) 0.6626(3) 0.0394(9) Uani 1 1 d . . . H6 H 0.0650 0.9137 0.6142 0.047 Uiso 1 1 calc R . . C7 C 0.2602(4) 0.6417(3) 0.9430(3) 0.0303(8) Uani 1 1 d . . . C8 C 0.2474(4) 0.6638(3) 1.0433(3) 0.0334(8) Uani 1 1 d . . . C9 C 0.2419(4) 0.7909(3) 1.0795(3) 0.0341(8) Uani 1 1 d . . . C10 C 0.2549(4) 0.9358(3) 1.0281(3) 0.0430(10) Uani 1 1 d . . . H10 H 0.2719 0.9749 0.9499 0.052 Uiso 1 1 calc R . . C11 C 0.2423(5) 1.0251(4) 1.0937(3) 0.0475(10) Uani 1 1 d . . . H11 H 0.2516 1.1249 1.0580 0.057 Uiso 1 1 calc R . . C12 C 0.2173(4) 0.9738(4) 1.2065(3) 0.0437(10) Uani 1 1 d . . . H12 H 0.2109 1.0377 1.2474 0.052 Uiso 1 1 calc R . . C13 C 0.2011(4) 0.8253(4) 1.2627(3) 0.0385(9) Uani 1 1 d . . . C14 C 0.2161(4) 0.7386(3) 1.1962(3) 0.0365(9) Uani 1 1 d . . . C15 C 0.2011(4) 0.5889(4) 1.2382(3) 0.0381(9) Uani 1 1 d . . . C16 C 0.1711(5) 0.5234(4) 1.3497(3) 0.0455(10) Uani 1 1 d . . . H16 H 0.1595 0.4233 1.3800 0.055 Uiso 1 1 calc R . . C17 C 0.1580(5) 0.6085(4) 1.4187(3) 0.0506(10) Uani 1 1 d . . . H17 H 0.1378 0.5634 1.4962 0.061 Uiso 1 1 calc R . . C18 C 0.1733(5) 0.7543(4) 1.3783(3) 0.0487(10) Uani 1 1 d . . . H18 H 0.1652 0.8071 1.4278 0.058 Uiso 1 1 calc R . . C19 C 0.2225(4) 0.5419(3) 1.1412(3) 0.0343(8) Uani 1 1 d . . . C20 C 0.2591(4) 0.4966(3) 0.9475(3) 0.0346(8) Uani 1 1 d . . . C21 C 0.2805(4) 0.4500(3) 0.8485(3) 0.0349(9) Uani 1 1 d . . . C22 C 0.1934(4) 0.3371(4) 0.8467(3) 0.0439(10) Uani 1 1 d . . . H22 H 0.1178 0.2933 0.9076 0.053 Uiso 1 1 calc R . . C23 C 0.2157(5) 0.2887(4) 0.7582(3) 0.0526(11) Uani 1 1 d . . . H23 H 0.1564 0.2111 0.7588 0.063 Uiso 1 1 calc R . . C24 C 0.3231(5) 0.3515(4) 0.6690(4) 0.0605(12) Uani 1 1 d . . . H24 H 0.3384 0.3168 0.6084 0.073 Uiso 1 1 calc R . . C25 C 0.4087(5) 0.4647(4) 0.6670(3) 0.0540(11) Uani 1 1 d . . . H25 H 0.4805 0.5097 0.6042 0.065 Uiso 1 1 calc R . . C26 C 0.3899(5) 0.5132(4) 0.7572(3) 0.0449(10) Uani 1 1 d . . . H26 H 0.4516 0.5894 0.7567 0.054 Uiso 1 1 calc R . . N1 N 0.3010(4) 1.0867(3) 0.5222(2) 0.0466(8) Uani 1 1 d . . . N2 N 0.2163(4) 0.4090(3) 1.1416(2) 0.0447(8) Uani 1 1 d . . . N3 N 0.2389(4) 0.3869(3) 1.0425(2) 0.0436(8) Uani 1 1 d . . . O1 O 0.4231(3) 1.1582(3) 0.4961(2) 0.0518(7) Uani 1 1 d . . . O2 O 0.1915(4) 1.1026(3) 0.4608(2) 0.0820(11) 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 C1 0.047(2) 0.036(2) 0.0236(19) -0.0098(15) 0.0008(16) -0.0025(17) C2 0.044(2) 0.037(2) 0.036(2) -0.0144(17) 0.0004(17) -0.0106(16) C3 0.044(2) 0.038(2) 0.031(2) -0.0111(17) -0.0063(16) -0.0096(17) C4 0.038(2) 0.0291(19) 0.035(2) -0.0175(16) -0.0006(16) -0.0041(15) C5 0.037(2) 0.036(2) 0.040(2) -0.0113(17) -0.0025(17) -0.0073(16) C6 0.042(2) 0.040(2) 0.037(2) -0.0145(17) -0.0044(17) -0.0037(17) C7 0.036(2) 0.0269(19) 0.0301(19) -0.0108(15) -0.0017(15) -0.0070(15) C8 0.040(2) 0.0284(19) 0.031(2) -0.0080(15) -0.0042(16) -0.0049(15) C9 0.042(2) 0.0279(19) 0.034(2) -0.0112(15) -0.0057(16) -0.0056(15) C10 0.064(3) 0.031(2) 0.037(2) -0.0121(16) -0.0074(18) -0.0119(18) C11 0.064(3) 0.029(2) 0.053(3) -0.0150(18) -0.012(2) -0.0056(18) C12 0.050(2) 0.043(2) 0.049(2) -0.0271(19) -0.0110(19) -0.0027(18) C13 0.039(2) 0.043(2) 0.036(2) -0.0148(17) -0.0047(16) -0.0060(17) C14 0.043(2) 0.034(2) 0.036(2) -0.0153(16) -0.0068(17) -0.0033(16) C15 0.041(2) 0.037(2) 0.035(2) -0.0106(17) -0.0029(17) -0.0041(16) C16 0.059(3) 0.039(2) 0.035(2) -0.0058(17) -0.0070(19) -0.0053(18) C17 0.057(3) 0.060(3) 0.034(2) -0.0134(19) -0.0033(19) -0.009(2) C18 0.048(3) 0.063(3) 0.041(2) -0.025(2) -0.0032(18) -0.004(2) C19 0.043(2) 0.028(2) 0.033(2) -0.0114(16) -0.0048(16) -0.0036(15) C20 0.037(2) 0.027(2) 0.039(2) -0.0095(17) -0.0060(17) -0.0026(15) C21 0.041(2) 0.0283(19) 0.039(2) -0.0158(16) -0.0107(17) 0.0029(16) C22 0.048(2) 0.041(2) 0.048(2) -0.0207(18) -0.0125(19) -0.0004(17) C23 0.064(3) 0.044(2) 0.062(3) -0.031(2) -0.019(2) 0.000(2) C24 0.070(3) 0.062(3) 0.066(3) -0.044(2) -0.014(3) 0.007(2) C25 0.061(3) 0.062(3) 0.047(3) -0.030(2) -0.001(2) -0.002(2) C26 0.047(2) 0.045(2) 0.052(2) -0.0285(19) -0.0046(19) -0.0003(18) N1 0.062(2) 0.042(2) 0.0337(19) -0.0118(15) 0.0014(17) -0.0073(17) N2 0.064(2) 0.0325(18) 0.0372(18) -0.0102(14) -0.0018(15) -0.0092(15) N3 0.064(2) 0.0266(17) 0.0432(19) -0.0144(14) -0.0056(16) -0.0051(14) O1 0.072(2) 0.0433(16) 0.0389(15) -0.0115(12) 0.0061(13) -0.0151(14) O2 0.083(2) 0.100(3) 0.0469(19) 0.0072(17) -0.0296(18) -0.0208(19) _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 C1 C6 1.379(4) . ? C1 C2 1.384(4) . ? C1 N1 1.480(4) . ? C2 C3 1.382(4) . ? C2 H2 0.9500 . ? C3 C4 1.388(4) . ? C3 H3 0.9500 . ? C4 C5 1.392(5) . ? C4 C7 1.505(4) . ? C5 C6 1.384(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.378(4) . ? C7 C20 1.428(4) . ? C8 C19 1.436(4) . ? C8 C9 1.487(4) . ? C9 C10 1.379(4) . ? C9 C14 1.415(4) . ? C10 C11 1.413(5) . ? C10 H10 0.9500 . ? C11 C12 1.369(5) . ? C11 H11 0.9500 . ? C12 C13 1.422(5) . ? C12 H12 0.9500 . ? C13 C14 1.400(4) . ? C13 C18 1.421(5) . ? C14 C15 1.416(4) . ? C15 C16 1.370(5) . ? C15 C19 1.467(4) . ? C16 C17 1.414(5) . ? C16 H16 0.9500 . ? C17 C18 1.380(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 N2 1.329(4) . ? C20 N3 1.344(4) . ? C20 C21 1.490(4) . ? C21 C22 1.398(4) . ? C21 C26 1.399(5) . ? C22 C23 1.372(5) . ? C22 H22 0.9500 . ? C23 C24 1.372(5) . ? C23 H23 0.9500 . ? C24 C25 1.377(5) . ? C24 H24 0.9500 . ? C25 C26 1.393(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N1 O2 1.220(4) . ? N1 O1 1.232(4) . ? N2 N3 1.360(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 C1 C2 122.7(3) . . ? C6 C1 N1 118.5(3) . . ? C2 C1 N1 118.8(3) . . ? C3 C2 C1 118.3(3) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 C7 120.7(3) . . ? C5 C4 C7 119.7(3) . . ? C6 C5 C4 120.6(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C1 C6 C5 118.2(3) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? C8 C7 C20 116.0(3) . . ? C8 C7 C4 122.3(3) . . ? C20 C7 C4 121.7(3) . . ? C7 C8 C19 117.5(3) . . ? C7 C8 C9 135.3(3) . . ? C19 C8 C9 107.0(3) . . ? C10 C9 C14 118.1(3) . . ? C10 C9 C8 135.9(3) . . ? C14 C9 C8 105.9(3) . . ? C9 C10 C11 118.8(3) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C12 C11 C10 122.7(3) . . ? C12 C11 H11 118.6 . . ? C10 C11 H11 118.6 . . ? C11 C12 C13 120.2(3) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C18 116.2(3) . . ? C14 C13 C12 116.0(3) . . ? C18 C13 C12 127.8(3) . . ? C13 C14 C15 123.5(3) . . ? C13 C14 C9 124.0(3) . . ? C15 C14 C9 112.4(3) . . ? C16 C15 C14 119.1(3) . . ? C16 C15 C19 135.4(3) . . ? C14 C15 C19 105.5(3) . . ? C15 C16 C17 118.3(3) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C18 C17 C16 122.8(4) . . ? C18 C17 H17 118.6 . . ? C16 C17 H17 118.6 . . ? C17 C18 C13 120.0(3) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? N2 C19 C8 124.4(3) . . ? N2 C19 C15 126.4(3) . . ? C8 C19 C15 109.2(3) . . ? N3 C20 C7 123.2(3) . . ? N3 C20 C21 112.7(3) . . ? C7 C20 C21 124.1(3) . . ? C22 C21 C26 118.2(3) . . ? C22 C21 C20 119.8(3) . . ? C26 C21 C20 122.0(3) . . ? C23 C22 C21 120.9(4) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C22 120.5(4) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 120.2(4) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C24 C25 C26 120.0(4) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.2(3) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? O2 N1 O1 123.0(3) . . ? O2 N1 C1 118.7(3) . . ? O1 N1 C1 118.3(3) . . ? C19 N2 N3 117.6(3) . . ? C20 N3 N2 121.1(3) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.293 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 935875'