# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email tpunni@iitg.ernet.in _publ_contact_author_name 'T. Punniyamurthy' _publ_author_name 'T Punniyamurthy' data_13b _database_code_depnum_ccdc_archive 'CCDC 863007' #TrackingRef '13b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 N2' _chemical_formula_weight 292.41 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' _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 8.8353(18) _cell_length_b 10.145(2) _cell_length_c 11.616(4) _cell_angle_alpha 106.121(18) _cell_angle_beta 109.391(19) _cell_angle_gamma 101.989(13) _cell_volume 890.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2205 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 22.73 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.091 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details Multi-scan _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10566 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 24.31 _reflns_number_total 2900 _reflns_number_gt 2049 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1083P)^2^+0.1191P] 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 2900 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1902 _refine_ls_wR_factor_gt 0.1729 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 C3 C -0.0666(3) 0.5766(2) 0.31699(19) 0.0568(6) Uani 1 1 d . . . C2 C 0.0538(3) 0.7022(2) 0.42200(19) 0.0535(5) Uani 1 1 d . . . C9 C 0.1892(3) 0.8295(2) 0.7517(2) 0.0650(6) Uani 1 1 d . . . H9 H 0.2222 0.7472 0.7422 0.078 Uiso 1 1 calc R . . C8 C 0.0701(3) 0.8394(2) 0.64595(19) 0.0538(5) Uani 1 1 d . . . C7 C 0.0249(3) 0.9627(3) 0.6611(2) 0.0713(7) Uani 1 1 d . . . H7 H -0.0555 0.9703 0.5897 0.086 Uiso 1 1 calc R . . C12 C 0.0994(3) 1.0760(3) 0.7833(2) 0.0757(7) Uani 1 1 d . . . H12 H 0.0685 1.1593 0.7924 0.091 Uiso 1 1 calc R . . C10 C 0.2599(3) 0.9432(3) 0.8726(2) 0.0696(7) Uani 1 1 d . . . H10 H 0.3390 0.9346 0.9440 0.084 Uiso 1 1 calc R . . C1 C 0.1986(3) 0.7799(2) 0.4178(2) 0.0649(6) Uani 1 1 d . . . H1 H 0.2767 0.8629 0.4893 0.078 Uiso 1 1 calc R . . C4 C -0.0405(3) 0.5282(3) 0.2030(2) 0.0713(7) Uani 1 1 d . . . H4 H -0.1187 0.4456 0.1311 0.086 Uiso 1 1 calc R . . C6 C 0.2246(3) 0.7315(3) 0.3053(3) 0.0750(7) Uani 1 1 d . . . C5 C 0.1047(4) 0.6063(3) 0.1998(3) 0.0796(8) Uani 1 1 d . . . H5 H 0.1237 0.5742 0.1243 0.095 Uiso 1 1 calc R . . N2 N -0.0070(2) 0.72161(17) 0.51936(15) 0.0547(5) Uani 1 1 d . . . N1 N -0.1965(2) 0.51988(19) 0.34945(17) 0.0625(5) Uani 1 1 d . . . C13 C -0.1560(3) 0.6080(2) 0.4696(2) 0.0581(6) Uani 1 1 d . . . C11 C 0.2182(3) 1.0682(2) 0.8918(2) 0.0642(6) Uani 1 1 d . . . C14 C 0.3002(4) 1.1917(3) 1.0254(3) 0.0882(8) Uani 1 1 d . . . H14 H 0.3740 1.1580 1.0861 0.106 Uiso 1 1 calc R . . C16 C 0.4133(5) 1.3235(4) 1.0257(4) 0.1396(16) Uani 1 1 d . . . H16A H 0.4921 1.2968 0.9912 0.209 Uiso 1 1 calc R . . H16B H 0.4749 1.3937 1.1142 0.209 Uiso 1 1 calc R . . H16C H 0.3457 1.3646 0.9720 0.209 Uiso 1 1 calc R . . C15 C 0.1730(6) 1.2225(4) 1.0773(3) 0.1415(16) Uani 1 1 d . . . H15A H 0.0981 1.2574 1.0215 0.212 Uiso 1 1 calc R . . H15B H 0.2306 1.2951 1.1650 0.212 Uiso 1 1 calc R . . H15C H 0.1081 1.1350 1.0789 0.212 Uiso 1 1 calc R . . C18 C 0.5127(5) 0.7551(6) 0.3144(6) 0.189(3) Uani 1 1 d . . . H18A H 0.4766 0.6629 0.2441 0.283 Uiso 1 1 calc R . . H18B H 0.5422 0.7420 0.3968 0.283 Uiso 1 1 calc R . . H18C H 0.6099 0.8203 0.3160 0.283 Uiso 1 1 calc R . . C17 C 0.3820(4) 0.8129(4) 0.2944(4) 0.1133(11) Uani 1 1 d . . . H17 H 0.4321 0.8857 0.3843 0.136 Uiso 1 1 calc R . . C19 C 0.3590(5) 0.9119(6) 0.2339(6) 0.182(3) Uani 1 1 d . . . H19A H 0.4672 0.9695 0.2444 0.273 Uiso 1 1 calc R . . H19B H 0.3070 0.9742 0.2736 0.273 Uiso 1 1 calc R . . H19C H 0.2868 0.8605 0.1418 0.273 Uiso 1 1 calc R . . C20 C -0.2554(3) 0.5902(3) 0.5486(2) 0.0768(7) Uani 1 1 d . . . H20A H -0.3579 0.5084 0.4959 0.115 Uiso 1 1 calc R . . H20B H -0.2837 0.6765 0.5767 0.115 Uiso 1 1 calc R . . H20C H -0.1888 0.5743 0.6244 0.115 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C3 0.0636(13) 0.0505(12) 0.0516(12) 0.0147(9) 0.0224(10) 0.0185(10) C2 0.0578(12) 0.0495(12) 0.0528(12) 0.0157(9) 0.0247(10) 0.0185(9) C9 0.0680(14) 0.0526(13) 0.0621(13) 0.0131(11) 0.0204(11) 0.0185(11) C8 0.0560(12) 0.0482(12) 0.0499(12) 0.0098(9) 0.0230(10) 0.0128(9) C7 0.0849(17) 0.0647(15) 0.0565(13) 0.0147(11) 0.0216(12) 0.0333(13) C12 0.0982(19) 0.0572(14) 0.0692(15) 0.0118(12) 0.0362(14) 0.0346(13) C10 0.0720(15) 0.0623(15) 0.0555(13) 0.0130(11) 0.0148(11) 0.0167(12) C1 0.0638(14) 0.0560(13) 0.0723(14) 0.0191(11) 0.0322(12) 0.0146(11) C4 0.0895(17) 0.0626(14) 0.0538(13) 0.0117(11) 0.0298(12) 0.0236(13) C6 0.0829(17) 0.0768(17) 0.0865(17) 0.0381(14) 0.0511(15) 0.0311(14) C5 0.106(2) 0.0877(19) 0.0738(16) 0.0367(15) 0.0577(16) 0.0455(17) N2 0.0556(10) 0.0489(10) 0.0502(10) 0.0086(8) 0.0225(8) 0.0116(8) N1 0.0603(11) 0.0557(11) 0.0565(11) 0.0110(9) 0.0207(9) 0.0093(8) C13 0.0550(12) 0.0541(12) 0.0583(13) 0.0157(10) 0.0227(10) 0.0133(10) C11 0.0688(14) 0.0582(14) 0.0538(13) 0.0104(10) 0.0259(11) 0.0120(11) C14 0.111(2) 0.0703(17) 0.0634(15) 0.0061(12) 0.0354(15) 0.0200(15) C16 0.148(3) 0.086(2) 0.103(2) -0.0112(19) 0.034(2) -0.027(2) C15 0.177(4) 0.127(3) 0.093(2) -0.011(2) 0.077(3) 0.033(3) C18 0.097(3) 0.245(6) 0.317(7) 0.185(6) 0.113(4) 0.084(3) C17 0.109(3) 0.133(3) 0.151(3) 0.077(2) 0.092(2) 0.046(2) C19 0.118(3) 0.234(6) 0.276(6) 0.202(6) 0.095(4) 0.048(3) C20 0.0690(15) 0.0824(17) 0.0792(16) 0.0261(13) 0.0401(13) 0.0159(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 N1 1.387(3) . ? C3 C4 1.391(3) . ? C3 C2 1.399(3) . ? C2 C1 1.380(3) . ? C2 N2 1.389(2) . ? C9 C8 1.371(3) . ? C9 C10 1.383(3) . ? C8 C7 1.374(3) . ? C8 N2 1.441(2) . ? C7 C12 1.389(3) . ? C12 C11 1.381(3) . ? C10 C11 1.373(3) . ? C1 C6 1.375(3) . ? C4 C5 1.379(4) . ? C6 C5 1.397(4) . ? C6 C17 1.527(4) . ? N2 C13 1.375(3) . ? N1 C13 1.311(3) . ? C13 C20 1.486(3) . ? C11 C14 1.517(3) . ? C14 C15 1.489(5) . ? C14 C16 1.492(4) . ? C18 C17 1.382(5) . ? C17 C19 1.388(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 N1 C3 C4 130.9(2) . . ? N1 C3 C2 110.21(18) . . ? C4 C3 C2 118.8(2) . . ? C1 C2 N2 132.13(19) . . ? C1 C2 C3 122.68(19) . . ? N2 C2 C3 105.18(18) . . ? C8 C9 C10 119.3(2) . . ? C9 C8 C7 119.64(19) . . ? C9 C8 N2 120.34(18) . . ? C7 C8 N2 120.02(19) . . ? C8 C7 C12 119.9(2) . . ? C11 C12 C7 121.7(2) . . ? C11 C10 C9 122.8(2) . . ? C6 C1 C2 118.4(2) . . ? C5 C4 C3 118.1(2) . . ? C1 C6 C5 119.3(2) . . ? C1 C6 C17 120.9(3) . . ? C5 C6 C17 119.8(3) . . ? C4 C5 C6 122.7(2) . . ? C13 N2 C2 106.33(16) . . ? C13 N2 C8 127.22(18) . . ? C2 N2 C8 126.44(17) . . ? C13 N1 C3 105.10(17) . . ? N1 C13 N2 113.18(19) . . ? N1 C13 C20 125.2(2) . . ? N2 C13 C20 121.63(19) . . ? C10 C11 C12 116.7(2) . . ? C10 C11 C14 121.4(2) . . ? C12 C11 C14 121.9(2) . . ? C15 C14 C16 113.3(3) . . ? C15 C14 C11 112.1(3) . . ? C16 C14 C11 112.1(2) . . ? C18 C17 C19 126.7(3) . . ? C18 C17 C6 116.2(3) . . ? C19 C17 C6 114.9(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.31 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.222 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.036 # Attachment '16b.cif' data_16b _database_code_depnum_ccdc_archive 'CCDC 863008' #TrackingRef '16b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 N3 O2' _chemical_formula_weight 329.35 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 8.2036(6) _cell_length_b 10.3079(8) _cell_length_c 10.9919(9) _cell_angle_alpha 76.796(5) _cell_angle_beta 78.813(5) _cell_angle_gamma 70.229(5) _cell_volume 844.64(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details multi-scan _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 9825 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3053 _reflns_number_gt 1869 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 3053 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1784 _refine_ls_wR_factor_gt 0.1387 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 N1 N 0.3009(3) 0.6936(2) 0.4305(3) 0.0723(7) Uani 1 1 d . . . O2 O 0.1880(3) 0.6884(3) 0.3748(2) 0.1029(8) Uani 1 1 d . . . O1 O 0.2717(3) 0.7270(3) 0.5345(3) 0.1050(8) Uani 1 1 d . . . N2 N 0.9948(2) 0.55663(19) 0.19826(16) 0.0508(5) Uani 1 1 d . . . N3 N 1.2385(3) 0.5609(2) 0.06443(17) 0.0580(6) Uani 1 1 d . . . C1 C 0.4824(3) 0.6557(2) 0.3693(2) 0.0524(6) Uani 1 1 d . . . C4 C 0.8183(3) 0.5909(2) 0.2559(2) 0.0478(6) Uani 1 1 d . . . C3 C 0.7801(3) 0.6175(3) 0.3774(2) 0.0571(6) Uani 1 1 d . . . H3 H 0.8694 0.6130 0.4205 0.069 Uiso 1 1 calc R . . C7 C 1.1253(3) 0.4337(2) 0.2378(2) 0.0489(6) Uani 1 1 d . . . C12 C 1.2738(3) 0.4387(3) 0.1538(2) 0.0533(6) Uani 1 1 d . . . C6 C 0.5170(3) 0.6279(2) 0.2490(2) 0.0604(7) Uani 1 1 d . . . H6 H 0.4273 0.6315 0.2067 0.073 Uiso 1 1 calc R . . C5 C 0.6870(3) 0.5946(2) 0.1924(2) 0.0574(6) Uani 1 1 d . . . H5 H 0.7136 0.5745 0.1112 0.069 Uiso 1 1 calc R . . C2 C 0.6109(3) 0.6506(3) 0.4348(2) 0.0593(7) Uani 1 1 d . . . H2 H 0.5841 0.6691 0.5165 0.071 Uiso 1 1 calc R . . C14 C 1.0726(3) 0.6278(2) 0.0928(2) 0.0526(6) Uani 1 1 d . . . C8 C 1.1199(3) 0.3217(3) 0.3327(2) 0.0580(7) Uani 1 1 d . . . H8 H 1.0181 0.3214 0.3874 0.070 Uiso 1 1 calc R . . C10 C 1.4223(4) 0.2160(3) 0.2605(3) 0.0709(8) Uani 1 1 d . . . H10 H 1.5238 0.1408 0.2699 0.085 Uiso 1 1 calc R . . C15 C 0.9802(3) 0.7620(3) 0.0189(2) 0.0588(7) Uani 1 1 d . . . C9 C 1.2708(3) 0.2094(3) 0.3439(2) 0.0638(7) Uani 1 1 d . . . C11 C 1.4276(3) 0.3280(3) 0.1657(2) 0.0654(7) Uani 1 1 d . . . H11 H 1.5297 0.3297 0.1119 0.078 Uiso 1 1 calc R . . C20 C 1.0404(4) 0.7890(3) -0.1096(2) 0.0709(8) Uani 1 1 d . . . H20 H 1.1331 0.7222 -0.1457 0.085 Uiso 1 1 calc R . . C16 C 0.8418(4) 0.8637(3) 0.0698(3) 0.0777(8) Uani 1 1 d . . . H16 H 0.8009 0.8483 0.1552 0.093 Uiso 1 1 calc R . . C13 C 1.2708(4) 0.0819(3) 0.4452(3) 0.0943(10) Uani 1 1 d . . . H13A H 1.3022 0.0938 0.5207 0.141 Uiso 1 1 calc R . . H13B H 1.3537 0.0000 0.4168 0.141 Uiso 1 1 calc R . . H13C H 1.1564 0.0710 0.4622 0.141 Uiso 1 1 calc R . . C19 C 0.9621(5) 0.9147(4) -0.1825(3) 0.0938(10) Uani 1 1 d . . . H19 H 1.0026 0.9323 -0.2678 0.113 Uiso 1 1 calc R . . C17 C 0.7641(5) 0.9881(3) -0.0059(4) 0.0977(11) Uani 1 1 d . . . H17 H 0.6692 1.0550 0.0284 0.117 Uiso 1 1 calc R . . C18 C 0.8255(6) 1.0138(4) -0.1308(4) 0.1053(12) Uani 1 1 d . . . H18 H 0.7744 1.0987 -0.1807 0.126 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 N1 0.0484(15) 0.0646(15) 0.0945(18) -0.0012(13) 0.0044(14) -0.0210(11) O2 0.0489(13) 0.134(2) 0.1156(17) -0.0005(15) -0.0072(12) -0.0311(13) O1 0.0732(15) 0.124(2) 0.1181(18) -0.0497(16) 0.0337(14) -0.0374(14) N2 0.0413(11) 0.0568(12) 0.0520(10) -0.0131(9) -0.0002(9) -0.0131(10) N3 0.0508(14) 0.0684(14) 0.0520(11) -0.0137(10) 0.0017(10) -0.0172(11) C1 0.0387(13) 0.0444(13) 0.0674(15) -0.0038(12) 0.0017(12) -0.0130(11) C4 0.0399(13) 0.0477(13) 0.0529(12) -0.0079(10) -0.0055(11) -0.0107(10) C3 0.0463(15) 0.0749(17) 0.0517(13) -0.0137(12) -0.0057(12) -0.0193(13) C7 0.0409(13) 0.0533(14) 0.0516(12) -0.0123(11) -0.0084(11) -0.0100(11) C12 0.0437(14) 0.0639(16) 0.0519(13) -0.0156(12) -0.0021(11) -0.0146(12) C6 0.0451(15) 0.0583(16) 0.0801(17) -0.0124(13) -0.0123(14) -0.0162(12) C5 0.0526(16) 0.0618(16) 0.0596(14) -0.0184(12) -0.0100(13) -0.0132(12) C2 0.0539(16) 0.0663(16) 0.0534(13) -0.0125(12) 0.0037(12) -0.0176(13) C14 0.0502(15) 0.0612(16) 0.0481(12) -0.0144(12) -0.0020(11) -0.0185(12) C8 0.0439(14) 0.0705(17) 0.0580(13) -0.0070(13) -0.0061(12) -0.0187(13) C10 0.0523(17) 0.0711(19) 0.0812(18) -0.0169(16) -0.0126(15) -0.0039(14) C15 0.0600(16) 0.0567(16) 0.0631(14) -0.0113(13) -0.0087(13) -0.0215(13) C9 0.0532(16) 0.0643(17) 0.0718(16) -0.0075(13) -0.0146(14) -0.0148(13) C11 0.0416(15) 0.0804(19) 0.0675(15) -0.0188(15) -0.0001(12) -0.0102(13) C20 0.083(2) 0.0698(18) 0.0604(15) -0.0049(14) -0.0124(15) -0.0266(16) C16 0.081(2) 0.0599(18) 0.0840(18) -0.0141(15) 0.0012(17) -0.0163(16) C13 0.083(2) 0.077(2) 0.112(2) 0.0170(18) -0.0331(19) -0.0219(17) C19 0.127(3) 0.083(2) 0.0721(18) 0.0063(18) -0.028(2) -0.038(2) C17 0.101(3) 0.058(2) 0.119(3) -0.0111(19) -0.017(2) -0.0059(18) C18 0.130(3) 0.068(2) 0.111(3) 0.008(2) -0.042(3) -0.022(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 N1 O1 1.225(3) . ? N1 O2 1.227(3) . ? N1 C1 1.470(3) . ? N2 C14 1.389(3) . ? N2 C7 1.397(3) . ? N2 C4 1.422(3) . ? N3 C14 1.313(3) . ? N3 C12 1.391(3) . ? C1 C2 1.368(3) . ? C1 C6 1.373(3) . ? C4 C5 1.378(3) . ? C4 C3 1.380(3) . ? C3 C2 1.370(3) . ? C7 C8 1.375(3) . ? C7 C12 1.387(3) . ? C12 C11 1.391(3) . ? C6 C5 1.374(3) . ? C14 C15 1.471(3) . ? C8 C9 1.383(3) . ? C10 C11 1.374(4) . ? C10 C9 1.406(4) . ? C15 C16 1.385(4) . ? C15 C20 1.400(3) . ? C9 C13 1.516(4) . ? C20 C19 1.376(4) . ? C16 C17 1.382(4) . ? C19 C18 1.366(5) . ? C17 C18 1.365(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 O1 N1 O2 124.0(3) . . ? O1 N1 C1 118.1(3) . . ? O2 N1 C1 117.9(3) . . ? C14 N2 C7 106.05(19) . . ? C14 N2 C4 129.82(19) . . ? C7 N2 C4 124.06(18) . . ? C14 N3 C12 105.41(19) . . ? C2 C1 C6 122.4(2) . . ? C2 C1 N1 118.4(2) . . ? C6 C1 N1 119.2(2) . . ? C5 C4 C3 120.2(2) . . ? C5 C4 N2 120.5(2) . . ? C3 C4 N2 119.3(2) . . ? C2 C3 C4 120.2(2) . . ? C8 C7 C12 123.2(2) . . ? C8 C7 N2 131.2(2) . . ? C12 C7 N2 105.5(2) . . ? C7 C12 N3 110.5(2) . . ? C7 C12 C11 119.7(2) . . ? N3 C12 C11 129.8(2) . . ? C1 C6 C5 118.5(2) . . ? C6 C5 C4 120.0(2) . . ? C1 C2 C3 118.6(2) . . ? N3 C14 N2 112.5(2) . . ? N3 C14 C15 123.2(2) . . ? N2 C14 C15 124.3(2) . . ? C7 C8 C9 117.7(2) . . ? C11 C10 C9 123.2(2) . . ? C16 C15 C20 118.6(3) . . ? C16 C15 C14 123.9(2) . . ? C20 C15 C14 117.5(2) . . ? C8 C9 C10 119.0(2) . . ? C8 C9 C13 119.9(2) . . ? C10 C9 C13 121.1(2) . . ? C10 C11 C12 117.1(2) . . ? C19 C20 C15 119.9(3) . . ? C17 C16 C15 120.2(3) . . ? C18 C19 C20 120.7(3) . . ? C18 C17 C16 120.5(3) . . ? C17 C18 C19 120.0(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.187 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.043