# Electronic Supplementary Material (ESI) for Green Chemistry # 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_a _database_code_depnum_ccdc_archive 'CCDC 853739' #TrackingRef 'A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 Br N O S' _chemical_formula_sum 'C21 H18 Br N O S' _chemical_formula_weight 412.33 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' S S 0.1246 0.1234 '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 Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.569(2) _cell_length_b 24.721(10) _cell_length_c 13.606(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.183(5) _cell_angle_gamma 90.00 _cell_volume 1837.5(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 2.359 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.844 _exptl_absorpt_correction_T_max 0.910 _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_reflns_number 11983 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 24.87 _reflns_number_total 3135 _reflns_number_gt 2164 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1073P)^2^+4.7951P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3135 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.2097 _refine_ls_wR_factor_gt 0.1894 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.005 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 Br1 Br 0.43441(18) 0.46997(3) 0.28574(6) 0.0843(4) Uani 1 1 d . . . S1 S -0.3541(4) 0.07215(8) 0.09668(14) 0.0688(6) Uani 1 1 d . . . O1 O 0.6050(11) 0.2451(2) 0.4190(4) 0.098(2) Uani 1 1 d . . . N1 N 0.0713(8) 0.11901(18) 0.2284(3) 0.0395(11) Uani 1 1 d . . . C1 C 0.3661(13) 0.3946(2) 0.2758(5) 0.0502(17) Uani 1 1 d . . . C2 C 0.1782(13) 0.3752(3) 0.3155(5) 0.0557(17) Uani 1 1 d . . . H2 H 0.0861 0.3982 0.3476 0.067 Uiso 1 1 calc R . . C3 C 0.1261(12) 0.3207(2) 0.3076(5) 0.0506(15) Uani 1 1 d . . . H3 H -0.0037 0.3069 0.3337 0.061 Uiso 1 1 calc R . . C4 C 0.2667(10) 0.2862(2) 0.2608(4) 0.0407(14) Uani 1 1 d . . . C5 C 0.2040(10) 0.2283(2) 0.2508(4) 0.0388(13) Uani 1 1 d . . . C6 C -0.0005(11) 0.2121(2) 0.1819(4) 0.0436(14) Uani 1 1 d . . . H6 H -0.0934 0.2375 0.1407 0.052 Uiso 1 1 calc R . . C7 C -0.0667(10) 0.1579(2) 0.1745(4) 0.0381(13) Uani 1 1 d . . . C8 C -0.2919(10) 0.1398(2) 0.1094(4) 0.0414(13) Uani 1 1 d . . . C9 C -0.6293(13) 0.0835(3) 0.0246(5) 0.0609(18) Uani 1 1 d . . . H9 H -0.7366 0.0560 -0.0015 0.073 Uiso 1 1 calc R . . C10 C 0.4527(12) 0.3080(2) 0.2210(5) 0.0517(16) Uani 1 1 d . . . H10 H 0.5461 0.2856 0.1883 0.062 Uiso 1 1 calc R . . C11 C 0.5040(12) 0.3622(3) 0.2283(5) 0.0554(17) Uani 1 1 d . . . H11 H 0.6312 0.3765 0.2012 0.066 Uiso 1 1 calc R . . C12 C 0.2756(10) 0.1337(2) 0.2907(4) 0.0403(13) Uani 1 1 d . . . C13 C 0.3476(10) 0.1874(2) 0.3076(4) 0.0383(13) Uani 1 1 d . . . C14 C 0.5642(12) 0.2010(2) 0.3864(5) 0.0508(16) Uani 1 1 d . . . C15 C 0.7286(11) 0.1542(2) 0.4259(5) 0.0476(15) Uani 1 1 d . . . H15A H 0.8321 0.1648 0.4888 0.057 Uiso 1 1 calc R . . H15B H 0.8341 0.1462 0.3789 0.057 Uiso 1 1 calc R . . C16 C 0.5883(11) 0.1034(2) 0.4427(4) 0.0433(14) Uani 1 1 d . . . C17 C 0.4207(11) 0.0881(2) 0.3442(4) 0.0469(14) Uani 1 1 d . . . H17A H 0.5197 0.0725 0.3001 0.056 Uiso 1 1 calc R . . H17B H 0.3081 0.0603 0.3576 0.056 Uiso 1 1 calc R . . C18 C 0.7690(12) 0.0573(3) 0.4763(6) 0.0623(19) Uani 1 1 d . . . H18A H 0.8720 0.0665 0.5392 0.093 Uiso 1 1 calc R . . H18B H 0.8682 0.0516 0.4269 0.093 Uiso 1 1 calc R . . H18C H 0.6802 0.0248 0.4841 0.093 Uiso 1 1 calc R . . C19 C 0.4363(12) 0.1137(3) 0.5221(4) 0.0527(16) Uani 1 1 d . . . H19A H 0.3157 0.1409 0.4987 0.079 Uiso 1 1 calc R . . H19B H 0.5409 0.1259 0.5826 0.079 Uiso 1 1 calc R . . H19C H 0.3561 0.0808 0.5351 0.079 Uiso 1 1 calc R . . C20 C -0.6801(12) 0.1361(3) 0.0082(4) 0.0537(16) Uani 1 1 d . . . H20 H -0.8262 0.1480 -0.0310 0.064 Uiso 1 1 calc R . . C21 C -0.4884(9) 0.1735(3) 0.0568(4) 0.0376(13) Uani 1 1 d . . . H21 H -0.4924 0.2111 0.0542 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1246(8) 0.0358(4) 0.0762(6) 0.0040(3) -0.0213(5) -0.0139(4) S1 0.0780(13) 0.0544(11) 0.0640(12) -0.0015(8) -0.0114(10) -0.0027(9) O1 0.121(5) 0.044(3) 0.095(4) -0.011(3) -0.061(4) -0.003(3) N1 0.051(3) 0.034(3) 0.030(2) -0.0056(19) -0.001(2) -0.002(2) C1 0.071(4) 0.025(3) 0.044(3) 0.003(2) -0.015(3) -0.003(3) C2 0.071(5) 0.046(4) 0.049(4) -0.010(3) 0.009(3) 0.010(3) C3 0.057(4) 0.044(4) 0.052(4) -0.006(3) 0.013(3) -0.002(3) C4 0.046(3) 0.042(3) 0.031(3) 0.000(2) -0.002(3) 0.001(3) C5 0.051(3) 0.032(3) 0.033(3) -0.004(2) 0.007(3) 0.000(2) C6 0.048(3) 0.044(3) 0.036(3) -0.001(3) 0.001(3) 0.008(3) C7 0.047(3) 0.037(3) 0.028(3) -0.002(2) 0.002(2) 0.005(2) C8 0.051(3) 0.041(3) 0.029(3) 0.000(2) 0.000(2) 0.001(3) C9 0.061(4) 0.070(5) 0.045(4) -0.007(3) -0.006(3) -0.014(4) C10 0.057(4) 0.040(3) 0.059(4) 0.002(3) 0.014(3) 0.005(3) C11 0.053(4) 0.055(4) 0.056(4) 0.008(3) 0.006(3) -0.002(3) C12 0.048(3) 0.042(3) 0.029(3) -0.002(2) 0.002(2) 0.002(3) C13 0.046(3) 0.039(3) 0.028(3) 0.000(2) 0.001(2) 0.002(2) C14 0.063(4) 0.038(3) 0.045(3) 0.001(3) -0.005(3) -0.004(3) C15 0.046(3) 0.050(4) 0.042(3) 0.005(3) -0.001(3) -0.006(3) C16 0.044(3) 0.043(3) 0.039(3) 0.007(3) -0.001(3) 0.000(3) C17 0.055(4) 0.041(3) 0.041(3) -0.003(3) -0.001(3) 0.003(3) C18 0.059(4) 0.056(4) 0.064(4) 0.015(3) -0.009(3) 0.002(3) C19 0.052(4) 0.069(4) 0.036(3) 0.005(3) 0.004(3) -0.002(3) C20 0.058(4) 0.058(4) 0.040(3) 0.002(3) -0.004(3) 0.006(3) C21 0.030(3) 0.061(4) 0.017(2) -0.009(2) -0.007(2) 0.004(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 Br1 C1 1.901(6) . ? S1 C9 1.676(7) . ? S1 C8 1.711(6) . ? O1 C14 1.183(8) . ? N1 C12 1.331(7) . ? N1 C7 1.354(7) . ? C1 C2 1.356(10) . ? C1 C11 1.357(9) . ? C2 C3 1.378(9) . ? C2 H2 0.9300 . ? C3 C4 1.393(8) . ? C3 H3 0.9300 . ? C4 C10 1.370(8) . ? C4 C5 1.473(7) . ? C5 C6 1.386(8) . ? C5 C13 1.422(8) . ? C6 C7 1.388(8) . ? C6 H6 0.9300 . ? C7 C8 1.458(8) . ? C8 C21 1.448(8) . ? C9 C20 1.339(10) . ? C9 H9 0.9300 . ? C10 C11 1.369(9) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.392(8) . ? C12 C17 1.492(8) . ? C13 C14 1.488(8) . ? C14 C15 1.507(8) . ? C15 C16 1.520(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C19 1.517(9) . ? C16 C17 1.525(8) . ? C16 C18 1.531(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.469(8) . ? C20 H20 0.9300 . ? C21 H21 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 C9 S1 C8 92.2(3) . . ? C12 N1 C7 118.5(5) . . ? C2 C1 C11 122.2(6) . . ? C2 C1 Br1 118.6(5) . . ? C11 C1 Br1 119.3(5) . . ? C1 C2 C3 118.8(6) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 120.4(6) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C10 C4 C3 118.3(6) . . ? C10 C4 C5 122.0(5) . . ? C3 C4 C5 119.5(5) . . ? C6 C5 C13 117.6(5) . . ? C6 C5 C4 119.5(5) . . ? C13 C5 C4 122.9(5) . . ? C7 C6 C5 120.0(5) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? N1 C7 C6 122.1(5) . . ? N1 C7 C8 116.3(5) . . ? C6 C7 C8 121.6(5) . . ? C21 C8 C7 127.1(5) . . ? C21 C8 S1 113.2(4) . . ? C7 C8 S1 119.6(4) . . ? C20 C9 S1 113.6(5) . . ? C20 C9 H9 123.2 . . ? S1 C9 H9 123.2 . . ? C11 C10 C4 121.3(6) . . ? C11 C10 H10 119.3 . . ? C4 C10 H10 119.3 . . ? C1 C11 C10 118.9(6) . . ? C1 C11 H11 120.5 . . ? C10 C11 H11 120.6 . . ? N1 C12 C13 123.3(5) . . ? N1 C12 C17 114.8(5) . . ? C13 C12 C17 121.9(5) . . ? C12 C13 C5 118.4(5) . . ? C12 C13 C14 120.1(5) . . ? C5 C13 C14 121.5(5) . . ? O1 C14 C13 123.3(6) . . ? O1 C14 C15 120.9(6) . . ? C13 C14 C15 115.8(5) . . ? C14 C15 C16 113.1(5) . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15B 109.0 . . ? C16 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C19 C16 C17 109.7(5) . . ? C19 C16 C15 110.0(5) . . ? C17 C16 C15 108.6(5) . . ? C19 C16 C18 109.7(5) . . ? C17 C16 C18 109.4(5) . . ? C15 C16 C18 109.5(5) . . ? C12 C17 C16 115.0(5) . . ? C12 C17 H17A 108.5 . . ? C16 C17 H17A 108.5 . . ? C12 C17 H17B 108.5 . . ? C16 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C9 C20 C21 115.1(6) . . ? C9 C20 H20 122.4 . . ? C21 C20 H20 122.4 . . ? C8 C21 C20 105.9(5) . . ? C8 C21 H21 127.0 . . ? C20 C21 H21 127.0 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 24.87 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.739 _refine_diff_density_min -0.592 _refine_diff_density_rms 0.095 _atom_sites_special_details ; The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.2, Nqual = -1, Ralpha = 0.044 ; data_a _database_code_depnum_ccdc_archive 'CCDC 853740' #TrackingRef 'A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H26 N2 O3' _chemical_formula_weight 450.52 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 ? _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 19.1534(10) _cell_length_b 10.4617(5) _cell_length_c 12.4228(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.230(2) _cell_angle_gamma 90.00 _cell_volume 2412.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details sadabs _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_reflns_number 28700 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 26.63 _reflns_number_total 5035 _reflns_number_gt 3025 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.3502P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5035 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0935 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1553 _refine_ls_wR_factor_gt 0.1301 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2308(2) 0.3442(3) 0.1414(2) 0.1956(17) Uani 1 1 d . . . O2 O 0.14701(13) 0.2653(3) 0.19722(19) 0.1331(10) Uani 1 1 d . . . O3 O 0.16938(8) 0.88911(15) 0.46601(11) 0.0680(4) Uani 1 1 d . . . N1 N 0.19397(16) 0.3395(3) 0.20599(18) 0.0914(7) Uani 1 1 d . . . N2 N 0.21073(8) 0.60207(16) 0.76481(13) 0.0543(4) Uani 1 1 d . . . H2 H 0.1929 0.5616 0.8121 0.065 Uiso 1 1 calc R . . C1 C 0.21219(12) 0.4278(2) 0.30132(17) 0.0640(6) Uani 1 1 d . . . C2 C 0.26043(14) 0.5247(2) 0.30305(18) 0.0705(6) Uani 1 1 d . . . H2A H 0.2834 0.5337 0.2457 0.085 Uiso 1 1 calc R . . C3 C 0.27445(11) 0.6091(2) 0.39166(16) 0.0588(5) Uani 1 1 d . . . H3 H 0.3064 0.6763 0.3927 0.071 Uiso 1 1 calc R . . C4 C 0.24167(9) 0.59503(19) 0.47864(14) 0.0479(5) Uani 1 1 d . . . C5 C 0.25794(9) 0.68702(19) 0.57700(14) 0.0474(5) Uani 1 1 d . . . H5 H 0.2835 0.7610 0.5570 0.057 Uiso 1 1 calc R . . C6 C 0.30780(9) 0.62052(18) 0.67657(15) 0.0460(4) Uani 1 1 d . . . C7 C 0.28233(9) 0.57846(18) 0.76148(15) 0.0475(5) Uani 1 1 d . . . C8 C 0.32294(10) 0.50641(19) 0.86033(15) 0.0490(5) Uani 1 1 d . . . C9 C 0.38454(11) 0.5531(2) 0.93042(17) 0.0607(5) Uani 1 1 d . . . H9 H 0.4040 0.6301 0.9141 0.073 Uiso 1 1 calc R . . C10 C 0.41810(13) 0.4859(2) 1.02582(18) 0.0701(6) Uani 1 1 d . . . H10 H 0.4594 0.5189 1.0734 0.084 Uiso 1 1 calc R . . C11 C 0.39099(15) 0.3724(3) 1.0501(2) 0.0766(7) Uani 1 1 d . . . H11 H 0.4138 0.3278 1.1138 0.092 Uiso 1 1 calc R . . C20 C 0.17975(12) 0.4093(2) 0.38726(18) 0.0696(6) Uani 1 1 d . . . H12 H 0.1482 0.3414 0.3862 0.084 Uiso 1 1 calc R . . C21 C 0.19507(11) 0.4938(2) 0.47505(18) 0.0647(6) Uani 1 1 d . . . H13 H 0.1733 0.4822 0.5336 0.078 Uiso 1 1 calc R . . C14 C 0.38279(10) 0.59779(19) 0.66731(14) 0.0477(5) Uani 1 1 d . . . C15 C 0.42597(11) 0.6995(2) 0.65299(18) 0.0621(6) Uani 1 1 d . . . H15 H 0.4083 0.7824 0.6522 0.075 Uiso 1 1 calc R . . C16 C 0.49465(12) 0.6801(3) 0.6399(2) 0.0737(7) Uani 1 1 d . . . H16 H 0.5229 0.7497 0.6311 0.088 Uiso 1 1 calc R . . C17 C 0.52126(12) 0.5587(3) 0.63994(19) 0.0738(7) Uani 1 1 d . . . H17 H 0.5674 0.5455 0.6305 0.089 Uiso 1 1 calc R . . C18 C 0.47944(13) 0.4569(3) 0.65396(19) 0.0725(7) Uani 1 1 d . . . H18 H 0.4975 0.3743 0.6543 0.087 Uiso 1 1 calc R . . C19 C 0.41059(11) 0.4755(2) 0.66754(17) 0.0598(5) Uani 1 1 d . . . H19 H 0.3828 0.4055 0.6769 0.072 Uiso 1 1 calc R . . C12 C 0.33082(16) 0.3246(3) 0.9815(2) 0.0946(9) Uani 1 1 d . . . H20 H 0.3128 0.2462 0.9972 0.114 Uiso 1 1 calc R . . C13 C 0.29590(14) 0.3921(2) 0.8878(2) 0.0804(7) Uani 1 1 d . . . H21 H 0.2535 0.3597 0.8427 0.097 Uiso 1 1 calc R . . C22 C 0.16885(10) 0.68740(19) 0.69502(15) 0.0491(5) Uani 1 1 d . . . C23 C 0.18997(10) 0.73488(18) 0.60643(14) 0.0472(5) Uani 1 1 d . . . C24 C 0.14904(10) 0.8352(2) 0.54114(15) 0.0523(5) Uani 1 1 d . . . C25 C 0.08025(11) 0.8792(2) 0.56843(18) 0.0638(6) Uani 1 1 d . . . H25A H 0.0463 0.9030 0.4997 0.077 Uiso 1 1 calc R . . H25B H 0.0907 0.9555 0.6139 0.077 Uiso 1 1 calc R . . C26 C 0.04402(10) 0.7824(2) 0.62877(17) 0.0584(5) Uani 1 1 d . . . C27 C -0.01447(13) 0.8483(3) 0.6738(2) 0.0836(8) Uani 1 1 d . . . H27A H -0.0345 0.7882 0.7164 0.125 Uiso 1 1 calc R . . H27B H -0.0518 0.8791 0.6129 0.125 Uiso 1 1 calc R . . H27C H 0.0062 0.9188 0.7202 0.125 Uiso 1 1 calc R . . C28 C 0.10177(10) 0.7297(2) 0.72615(16) 0.0583(5) Uani 1 1 d . . . H28A H 0.1143 0.7951 0.7830 0.070 Uiso 1 1 calc R . . H28B H 0.0819 0.6577 0.7579 0.070 Uiso 1 1 calc R . . C29 C 0.01044(13) 0.6738(3) 0.5503(2) 0.0820(7) Uani 1 1 d . . . H29A H 0.0469 0.6343 0.5205 0.123 Uiso 1 1 calc R . . H29B H -0.0267 0.7076 0.4906 0.123 Uiso 1 1 calc R . . H29C H -0.0098 0.6114 0.5905 0.123 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.324(4) 0.174(3) 0.141(2) -0.086(2) 0.157(3) -0.085(3) O2 0.1180(18) 0.171(2) 0.1084(17) -0.0715(17) 0.0245(14) -0.0401(17) O3 0.0786(10) 0.0804(11) 0.0500(8) 0.0175(7) 0.0256(7) 0.0132(8) N1 0.117(2) 0.0985(18) 0.0610(14) -0.0158(13) 0.0269(14) 0.0181(16) N2 0.0483(9) 0.0727(11) 0.0450(9) 0.0136(8) 0.0175(7) 0.0055(8) C1 0.0661(13) 0.0788(16) 0.0458(12) -0.0076(11) 0.0110(10) 0.0146(12) C2 0.0907(17) 0.0790(16) 0.0520(13) 0.0044(12) 0.0371(12) 0.0156(14) C3 0.0636(13) 0.0671(14) 0.0519(12) 0.0063(10) 0.0260(10) 0.0053(11) C4 0.0407(10) 0.0646(13) 0.0387(10) 0.0049(9) 0.0104(8) 0.0077(9) C5 0.0458(10) 0.0589(12) 0.0383(10) 0.0046(8) 0.0118(8) 0.0001(9) C6 0.0447(10) 0.0526(11) 0.0403(10) -0.0006(8) 0.0098(8) -0.0005(8) C7 0.0440(10) 0.0556(12) 0.0424(10) 0.0000(9) 0.0098(8) 0.0004(9) C8 0.0517(11) 0.0573(12) 0.0389(10) 0.0010(9) 0.0128(8) 0.0058(9) C9 0.0604(12) 0.0611(13) 0.0564(12) 0.0001(10) 0.0066(10) 0.0037(10) C10 0.0656(14) 0.0829(17) 0.0524(13) -0.0034(12) -0.0036(10) 0.0117(12) C11 0.0878(18) 0.0829(18) 0.0551(14) 0.0186(13) 0.0097(13) 0.0176(14) C20 0.0604(13) 0.0895(17) 0.0623(14) -0.0144(12) 0.0215(11) -0.0111(12) C21 0.0604(13) 0.0885(17) 0.0522(12) -0.0118(11) 0.0272(10) -0.0124(12) C14 0.0458(10) 0.0604(13) 0.0359(9) -0.0027(8) 0.0079(8) -0.0003(9) C15 0.0518(12) 0.0664(14) 0.0695(14) 0.0037(11) 0.0174(10) -0.0013(11) C16 0.0531(13) 0.0875(18) 0.0826(16) 0.0068(14) 0.0209(12) -0.0108(13) C17 0.0501(13) 0.110(2) 0.0628(14) 0.0001(14) 0.0171(11) 0.0113(14) C18 0.0700(15) 0.0786(17) 0.0714(15) -0.0029(13) 0.0219(12) 0.0202(13) C19 0.0591(12) 0.0607(13) 0.0616(13) -0.0033(10) 0.0184(10) 0.0035(11) C12 0.111(2) 0.0833(19) 0.0776(17) 0.0312(15) 0.0011(16) -0.0118(16) C13 0.0849(17) 0.0754(16) 0.0696(15) 0.0189(13) -0.0028(13) -0.0161(13) C22 0.0450(10) 0.0619(12) 0.0407(10) 0.0001(9) 0.0109(8) 0.0021(9) C23 0.0459(10) 0.0579(12) 0.0389(10) -0.0003(9) 0.0123(8) 0.0031(9) C24 0.0559(11) 0.0616(13) 0.0393(10) -0.0002(9) 0.0117(9) 0.0038(10) C25 0.0598(13) 0.0730(15) 0.0599(13) 0.0080(11) 0.0169(10) 0.0142(11) C26 0.0469(11) 0.0737(14) 0.0547(12) 0.0037(11) 0.0128(9) 0.0070(10) C27 0.0617(14) 0.105(2) 0.0906(18) 0.0118(15) 0.0310(13) 0.0227(14) C28 0.0496(12) 0.0779(15) 0.0500(11) 0.0033(10) 0.0172(9) 0.0063(10) C29 0.0626(14) 0.0998(19) 0.0776(16) -0.0074(14) 0.0059(12) -0.0035(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.192(3) . ? O2 N1 1.173(3) . ? O3 C24 1.233(2) . ? N1 C1 1.474(3) . ? N2 C22 1.360(2) . ? N2 C7 1.404(2) . ? N2 H2 0.8600 . ? C1 C2 1.368(3) . ? C1 C20 1.375(3) . ? C2 C3 1.385(3) . ? C2 H2A 0.9300 . ? C3 C4 1.384(3) . ? C3 H3 0.9300 . ? C4 C21 1.379(3) . ? C4 C5 1.526(3) . ? C5 C23 1.521(2) . ? C5 C6 1.532(2) . ? C5 H5 0.9800 . ? C6 C7 1.341(3) . ? C6 C14 1.488(3) . ? C7 C8 1.487(3) . ? C8 C9 1.373(3) . ? C8 C13 1.379(3) . ? C9 C10 1.392(3) . ? C9 H9 0.9300 . ? C10 C11 1.359(3) . ? C10 H10 0.9300 . ? C11 C12 1.349(4) . ? C11 H11 0.9300 . ? C20 C21 1.378(3) . ? C20 H12 0.9300 . ? C21 H13 0.9300 . ? C14 C19 1.385(3) . ? C14 C15 1.386(3) . ? C15 C16 1.379(3) . ? C15 H15 0.9300 . ? C16 C17 1.369(3) . ? C16 H16 0.9300 . ? C17 C18 1.369(3) . ? C17 H17 0.9300 . ? C18 C19 1.384(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C12 C13 1.385(3) . ? C12 H20 0.9300 . ? C13 H21 0.9300 . ? C22 C23 1.357(3) . ? C22 C28 1.497(3) . ? C23 C24 1.436(3) . ? C24 C25 1.511(3) . ? C25 C26 1.525(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C28 1.528(3) . ? C26 C29 1.532(3) . ? C26 C27 1.533(3) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 N1 O1 122.1(3) . . ? O2 N1 C1 120.9(2) . . ? O1 N1 C1 116.9(3) . . ? C22 N2 C7 121.60(16) . . ? C22 N2 H2 119.2 . . ? C7 N2 H2 119.2 . . ? C2 C1 C20 121.6(2) . . ? C2 C1 N1 120.2(2) . . ? C20 C1 N1 118.2(2) . . ? C1 C2 C3 118.9(2) . . ? C1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? C4 C3 C2 121.1(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C21 C4 C3 118.08(19) . . ? C21 C4 C5 120.89(16) . . ? C3 C4 C5 121.02(18) . . ? C23 C5 C4 112.44(15) . . ? C23 C5 C6 110.85(14) . . ? C4 C5 C6 108.92(15) . . ? C23 C5 H5 108.2 . . ? C4 C5 H5 108.2 . . ? C6 C5 H5 108.2 . . ? C7 C6 C14 123.60(16) . . ? C7 C6 C5 120.62(16) . . ? C14 C6 C5 115.61(15) . . ? C6 C7 N2 120.83(16) . . ? C6 C7 C8 126.75(16) . . ? N2 C7 C8 112.41(15) . . ? C9 C8 C13 117.92(19) . . ? C9 C8 C7 122.47(18) . . ? C13 C8 C7 119.47(18) . . ? C8 C9 C10 120.3(2) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 120.6(2) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 119.8(2) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C1 C20 C21 118.4(2) . . ? C1 C20 H12 120.8 . . ? C21 C20 H12 120.8 . . ? C20 C21 C4 121.90(19) . . ? C20 C21 H13 119.1 . . ? C4 C21 H13 119.1 . . ? C19 C14 C15 117.92(18) . . ? C19 C14 C6 121.69(18) . . ? C15 C14 C6 120.33(18) . . ? C16 C15 C14 121.2(2) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C17 C16 C15 120.2(2) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.5(2) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C17 C18 C19 120.7(2) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C14 120.5(2) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? C11 C12 C13 120.2(3) . . ? C11 C12 H20 119.9 . . ? C13 C12 H20 119.9 . . ? C8 C13 C12 121.1(2) . . ? C8 C13 H21 119.4 . . ? C12 C13 H21 119.4 . . ? C23 C22 N2 120.70(17) . . ? C23 C22 C28 123.20(18) . . ? N2 C22 C28 116.01(16) . . ? C22 C23 C24 119.71(17) . . ? C22 C23 C5 121.21(17) . . ? C24 C23 C5 119.05(16) . . ? O3 C24 C23 122.13(18) . . ? O3 C24 C25 119.07(18) . . ? C23 C24 C25 118.77(17) . . ? C24 C25 C26 115.80(18) . . ? C24 C25 H25A 108.3 . . ? C26 C25 H25A 108.3 . . ? C24 C25 H25B 108.3 . . ? C26 C25 H25B 108.3 . . ? H25A C25 H25B 107.4 . . ? C25 C26 C28 107.50(17) . . ? C25 C26 C29 110.51(18) . . ? C28 C26 C29 110.18(19) . . ? C25 C26 C27 110.02(19) . . ? C28 C26 C27 108.99(17) . . ? C29 C26 C27 109.60(19) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C22 C28 C26 113.74(16) . . ? C22 C28 H28A 108.8 . . ? C26 C28 H28A 108.8 . . ? C22 C28 H28B 108.8 . . ? C26 C28 H28B 108.8 . . ? H28A C28 H28B 107.7 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.63 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.230 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.034 data_a2 _database_code_depnum_ccdc_archive 'CCDC 884043' #TrackingRef 'cif-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H23 N2 O3' _chemical_formula_weight 387.44 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 ? _symmetry_space_group_name_H-M 'C 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' _cell_length_a 16.0558(4) _cell_length_b 13.0680(4) _cell_length_c 11.5754(4) _cell_angle_alpha 90.00 _cell_angle_beta 122.419(2) _cell_angle_gamma 90.00 _cell_volume 2050.20(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details sadabs _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_reflns_number 14019 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.94 _reflns_number_total 3966 _reflns_number_gt 3368 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1673P)^2^+0.5878P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 3966 _refine_ls_number_parameters 265 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1855 _refine_ls_wR_factor_gt 0.1694 _refine_ls_goodness_of_fit_ref 0.839 _refine_ls_restrained_S_all 0.839 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3230(5) 0.3616(2) 0.8005(9) 0.195(3) Uani 1 1 d . . . O2 O 0.2167(2) 0.81533(19) 0.6049(3) 0.0915(9) Uani 1 1 d . . . N1 N 0.39874(18) 1.04384(17) 0.9766(2) 0.0557(5) Uani 1 1 d . . . C8 C 0.45513(18) 0.97040(18) 1.0632(2) 0.0464(5) Uani 1 1 d . . . C9 C 0.52541(18) 1.0076(2) 1.2058(3) 0.0470(6) Uani 1 1 d . . . N2 N 0.3619(3) 0.4176(2) 0.7602(4) 0.0903(11) Uani 1 1 d . . . C1 C 0.3645(2) 0.5280(2) 0.7893(3) 0.0615(7) Uani 1 1 d . . . C2 C 0.4108(3) 0.5930(3) 0.7486(4) 0.0705(8) Uani 1 1 d . . . H3 H 0.4402 0.5685 0.7034 0.085 Uiso 1 1 calc R . . C3 C 0.4126(2) 0.6970(3) 0.7767(4) 0.0666(8) Uani 1 1 d . . . H4 H 0.4426 0.7427 0.7486 0.080 Uiso 1 1 calc R . . C4 C 0.37001(19) 0.73288(19) 0.8459(3) 0.0488(6) Uani 1 1 d . . . C5 C 0.37916(19) 0.84277(19) 0.8880(3) 0.0467(5) Uani 1 1 d . . . C15 C 0.45140(18) 0.86782(19) 1.0240(3) 0.0479(5) Uani 1 1 d . . . C14 C 0.5483(2) 0.9546(2) 1.3215(3) 0.0578(6) Uani 1 1 d . . . H8 H 0.5213 0.8901 1.3136 0.069 Uiso 1 1 calc R . . C13 C 0.6117(2) 0.9967(3) 1.4510(3) 0.0644(7) Uani 1 1 d . . . H9 H 0.6260 0.9602 1.5285 0.077 Uiso 1 1 calc R . . C12 C 0.6528(2) 1.0907(2) 1.4651(3) 0.0621(7) Uani 1 1 d . . . H10 H 0.6952 1.1180 1.5518 0.074 Uiso 1 1 calc R . . C17 C 0.3238(2) 0.66448(19) 0.8842(3) 0.0537(6) Uani 1 1 d . . . H11 H 0.2948 0.6883 0.9304 0.064 Uiso 1 1 calc R . . C18 C 0.3195(2) 0.5605(2) 0.8554(3) 0.0604(7) Uani 1 1 d . . . H12 H 0.2872 0.5147 0.8800 0.072 Uiso 1 1 calc R . . C6 C 0.3200(2) 0.9199(2) 0.7958(3) 0.0539(6) Uani 1 1 d . . . C19 C 0.2428(3) 0.9000(2) 0.6494(3) 0.0656(8) Uani 1 1 d . . . C20 C 0.2026(3) 0.9906(3) 0.5552(4) 0.0758(9) Uani 1 1 d . . . H15A H 0.1407 0.9715 0.4730 0.091 Uiso 1 1 calc R . . H15B H 0.2485 1.0094 0.5287 0.091 Uiso 1 1 calc R . . C21 C 0.1849(2) 1.0843(2) 0.6207(3) 0.0569(6) Uani 1 1 d . . . C23 C 0.1459(5) 1.1747(4) 0.5224(5) 0.1057(15) Uani 1 1 d . . . H17A H 0.1380 1.2327 0.5665 0.159 Uiso 1 1 calc R . . H17B H 0.0834 1.1571 0.4424 0.159 Uiso 1 1 calc R . . H1 H 0.1918 1.1913 0.4962 0.159 Uiso 1 1 calc R . . C24 C 0.1075(3) 1.0559(4) 0.6536(5) 0.0900(11) Uani 1 1 d . . . H18A H 0.1307 0.9989 0.7156 0.135 Uiso 1 1 calc R . . H18B H 0.0470 1.0376 0.5707 0.135 Uiso 1 1 calc R . . H18C H 0.0961 1.1133 0.6952 0.135 Uiso 1 1 calc R . . C22 C 0.2814(3) 1.1096(2) 0.7504(4) 0.0786(10) Uani 1 1 d . . . H19A H 0.2690 1.1607 0.8002 0.094 Uiso 1 1 calc R . . H19B H 0.3249 1.1402 0.7258 0.094 Uiso 1 1 calc R . . C7 C 0.3347(2) 1.0202(2) 0.8455(3) 0.0593(7) Uani 1 1 d . . . C16 C 0.5252(2) 0.7885(2) 1.1161(3) 0.0636(7) Uani 1 1 d . . . H21A H 0.5836 0.8217 1.1876 0.095 Uiso 1 1 calc R . . H21B H 0.5418 0.7458 1.0639 0.095 Uiso 1 1 calc R . . H21C H 0.4973 0.7473 1.1557 0.095 Uiso 1 1 calc R . . C11 C 0.6316(2) 1.1448(2) 1.3513(3) 0.0602(7) Uani 1 1 d . . . H22 H 0.6601 1.2086 1.3608 0.072 Uiso 1 1 calc R . . C10 C 0.5679(2) 1.1051(2) 1.2220(3) 0.0524(6) Uani 1 1 d . . . H23 H 0.5530 1.1430 1.1452 0.063 Uiso 1 1 calc R . . O3 O 0.3998(4) 0.3882(3) 0.7030(4) 0.1410(18) 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 O1 0.249(7) 0.0421(15) 0.384(10) -0.038(3) 0.229(8) -0.032(3) O2 0.0940(18) 0.0589(13) 0.0702(15) -0.0222(11) 0.0099(14) -0.0163(13) N1 0.0543(13) 0.0414(10) 0.0507(12) -0.0092(9) 0.0144(10) -0.0055(9) C8 0.0436(13) 0.0404(12) 0.0462(13) -0.0064(10) 0.0180(11) -0.0077(9) C9 0.0423(12) 0.0452(13) 0.0488(13) -0.0087(10) 0.0213(11) -0.0036(9) N2 0.085(2) 0.0567(17) 0.098(2) -0.0187(17) 0.028(2) 0.0126(16) C1 0.0523(15) 0.0433(13) 0.0614(16) -0.0113(11) 0.0122(13) 0.0042(11) C2 0.0605(18) 0.076(2) 0.076(2) -0.0220(16) 0.0371(17) -0.0018(15) C3 0.0658(18) 0.0641(17) 0.083(2) -0.0179(15) 0.0487(18) -0.0170(14) C4 0.0454(13) 0.0382(11) 0.0536(13) -0.0102(10) 0.0205(11) -0.0096(10) C5 0.0456(13) 0.0355(11) 0.0520(13) -0.0053(9) 0.0216(11) -0.0070(9) C15 0.0462(14) 0.0379(11) 0.0534(13) -0.0062(10) 0.0227(12) -0.0096(9) C14 0.0578(16) 0.0567(15) 0.0602(16) -0.0001(12) 0.0324(14) -0.0064(12) C13 0.0659(18) 0.075(2) 0.0485(14) 0.0025(13) 0.0283(14) 0.0083(15) C12 0.0546(15) 0.0680(18) 0.0476(14) -0.0143(13) 0.0168(12) 0.0039(13) C17 0.0638(16) 0.0386(12) 0.0603(15) -0.0068(11) 0.0343(14) -0.0051(11) C18 0.0686(18) 0.0369(12) 0.0664(16) -0.0067(12) 0.0300(15) -0.0080(12) C6 0.0538(15) 0.0432(13) 0.0515(14) -0.0063(11) 0.0194(13) -0.0094(11) C19 0.0680(19) 0.0511(15) 0.0536(15) -0.0115(12) 0.0167(14) -0.0125(13) C20 0.082(2) 0.082(2) 0.0577(17) -0.0089(15) 0.0341(17) -0.0081(18) C21 0.0542(15) 0.0556(15) 0.0476(13) -0.0008(11) 0.0185(12) 0.0005(12) C23 0.114(4) 0.079(3) 0.076(2) 0.015(2) 0.019(3) 0.005(2) C24 0.069(2) 0.113(3) 0.081(2) -0.004(2) 0.036(2) 0.002(2) C22 0.076(2) 0.0473(16) 0.070(2) -0.0021(13) 0.0114(18) -0.0011(14) C7 0.0554(16) 0.0402(12) 0.0542(15) -0.0036(11) 0.0106(13) -0.0046(11) C16 0.0585(17) 0.0476(14) 0.0620(16) -0.0034(12) 0.0173(14) 0.0002(12) C11 0.0609(17) 0.0471(13) 0.0608(16) -0.0163(12) 0.0249(14) -0.0083(12) C10 0.0555(15) 0.0468(13) 0.0503(13) -0.0057(10) 0.0252(13) -0.0044(11) O3 0.192(5) 0.094(2) 0.119(3) -0.026(2) 0.072(3) 0.054(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N2 1.206(7) . ? O2 C19 1.197(4) . ? N1 C8 1.331(3) . ? N1 C7 1.336(4) . ? C8 C15 1.406(3) . ? C8 C9 1.496(3) . ? C9 C14 1.371(4) . ? C9 C10 1.409(4) . ? N2 O3 1.179(5) . ? N2 C1 1.477(4) . ? C1 C2 1.368(5) . ? C1 C18 1.372(5) . ? C2 C3 1.393(5) . ? C2 H3 0.9300 . ? C3 C4 1.384(4) . ? C3 H4 0.9300 . ? C4 C17 1.378(4) . ? C4 C5 1.498(3) . ? C5 C6 1.404(4) . ? C5 C15 1.404(4) . ? C15 C16 1.504(4) . ? C14 C13 1.396(4) . ? C14 H8 0.9300 . ? C13 C12 1.362(5) . ? C13 H9 0.9300 . ? C12 C11 1.367(5) . ? C12 H10 0.9300 . ? C17 C18 1.392(4) . ? C17 H11 0.9300 . ? C18 H12 0.9300 . ? C6 C7 1.400(4) . ? C6 C19 1.491(4) . ? C19 C20 1.501(5) . ? C20 C21 1.544(5) . ? C20 H15A 0.9700 . ? C20 H15B 0.9700 . ? C21 C22 1.506(5) . ? C21 C23 1.523(5) . ? C21 C24 1.529(5) . ? C23 H17A 0.9600 . ? C23 H17B 0.9600 . ? C23 H1 0.9600 . ? C24 H18A 0.9600 . ? C24 H18B 0.9600 . ? C24 H18C 0.9600 . ? C22 C7 1.516(4) . ? C22 H19A 0.9700 . ? C22 H19B 0.9700 . ? C16 H21A 0.9600 . ? C16 H21B 0.9600 . ? C16 H21C 0.9600 . ? C11 C10 1.383(4) . ? C11 H22 0.9300 . ? C10 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 C8 N1 C7 119.2(2) . . ? N1 C8 C15 123.4(2) . . ? N1 C8 C9 113.7(2) . . ? C15 C8 C9 122.8(2) . . ? C14 C9 C10 118.0(2) . . ? C14 C9 C8 124.2(2) . . ? C10 C9 C8 117.7(2) . . ? O3 N2 O1 123.3(4) . . ? O3 N2 C1 119.1(4) . . ? O1 N2 C1 117.5(4) . . ? C2 C1 C18 123.1(3) . . ? C2 C1 N2 118.8(3) . . ? C18 C1 N2 118.1(3) . . ? C1 C2 C3 118.2(3) . . ? C1 C2 H3 120.9 . . ? C3 C2 H3 120.9 . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H4 119.6 . . ? C2 C3 H4 119.6 . . ? C17 C4 C3 119.0(2) . . ? C17 C4 C5 119.6(2) . . ? C3 C4 C5 121.4(2) . . ? C6 C5 C15 120.0(2) . . ? C6 C5 C4 122.2(2) . . ? C15 C5 C4 117.8(2) . . ? C5 C15 C8 116.8(2) . . ? C5 C15 C16 119.8(2) . . ? C8 C15 C16 123.2(2) . . ? C9 C14 C13 120.6(3) . . ? C9 C14 H8 119.7 . . ? C13 C14 H8 119.7 . . ? C12 C13 C14 120.8(3) . . ? C12 C13 H9 119.6 . . ? C14 C13 H9 119.6 . . ? C13 C12 C11 119.7(3) . . ? C13 C12 H10 120.1 . . ? C11 C12 H10 120.1 . . ? C4 C17 C18 121.5(3) . . ? C4 C17 H11 119.2 . . ? C18 C17 H11 119.2 . . ? C1 C18 C17 117.5(3) . . ? C1 C18 H12 121.2 . . ? C17 C18 H12 121.2 . . ? C7 C6 C5 117.6(3) . . ? C7 C6 C19 119.0(3) . . ? C5 C6 C19 123.4(2) . . ? O2 C19 C6 122.4(3) . . ? O2 C19 C20 120.1(3) . . ? C6 C19 C20 117.3(3) . . ? C19 C20 C21 113.0(3) . . ? C19 C20 H15A 109.0 . . ? C21 C20 H15A 109.0 . . ? C19 C20 H15B 109.0 . . ? C21 C20 H15B 109.0 . . ? H15A C20 H15B 107.8 . . ? C22 C21 C23 111.4(3) . . ? C22 C21 C24 110.1(3) . . ? C23 C21 C24 108.1(4) . . ? C22 C21 C20 107.6(3) . . ? C23 C21 C20 111.0(3) . . ? C24 C21 C20 108.5(3) . . ? C21 C23 H17A 109.5 . . ? C21 C23 H17B 109.5 . . ? H17A C23 H17B 109.5 . . ? C21 C23 H1 109.5 . . ? H17A C23 H1 109.5 . . ? H17B C23 H1 109.5 . . ? C21 C24 H18A 109.5 . . ? C21 C24 H18B 109.5 . . ? H18A C24 H18B 109.5 . . ? C21 C24 H18C 109.5 . . ? H18A C24 H18C 109.5 . . ? H18B C24 H18C 109.5 . . ? C21 C22 C7 115.7(3) . . ? C21 C22 H19A 108.4 . . ? C7 C22 H19A 108.4 . . ? C21 C22 H19B 108.4 . . ? C7 C22 H19B 108.4 . . ? H19A C22 H19B 107.4 . . ? N1 C7 C6 122.7(3) . . ? N1 C7 C22 116.0(2) . . ? C6 C7 C22 121.2(3) . . ? C15 C16 H21A 109.5 . . ? C15 C16 H21B 109.5 . . ? H21A C16 H21B 109.5 . . ? C15 C16 H21C 109.5 . . ? H21A C16 H21C 109.5 . . ? H21B C16 H21C 109.5 . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H22 119.8 . . ? C10 C11 H22 119.8 . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H23 119.8 . . ? C9 C10 H23 119.8 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.94 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.412 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.043