# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Danaboyina Ramaiah' _publ_contact_author_email rama@niist.res.in loop_ _publ_author_name D.Ramaiah R.Avirah C.Suresh S.Eringathodi data_1021parm(2e) _database_code_depnum_ccdc_archive 'CCDC 809673' #TrackingRef '- Crystallographic data of compounds 2e and 3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N O4' _chemical_formula_weight 339.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 7.7932(8) _cell_length_b 8.7008(9) _cell_length_c 24.571(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.845(2) _cell_angle_gamma 90.00 _cell_volume 1654.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1052 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 26.99 _exptl_crystal_description PLATES _exptl_crystal_colour 'WINE RED' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_T_max 0.9962 _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8006 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2903 _reflns_number_gt 2536 _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 ORTEP _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^)+(0.0723P)^2^+2.9841P] 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 2903 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0958 _refine_ls_wR_factor_ref 0.2061 _refine_ls_wR_factor_gt 0.1988 _refine_ls_goodness_of_fit_ref 1.263 _refine_ls_restrained_S_all 1.263 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1818(4) -0.0532(3) 0.24398(10) 0.0149(7) Uani 1 d . . . H1 H 0.1589 0.0089 0.2191 0.022 Uiso 1 calc R . . O2 O 0.0924(4) 0.3943(3) 0.65382(10) 0.0183(7) Uani 1 d . . . O3 O 0.2843(4) 0.1289(3) 0.72775(10) 0.0154(7) Uani 1 d . . . O4 O 0.3430(4) -0.0587(3) 0.61395(10) 0.0173(7) Uani 1 d . . . N1 N 0.0560(4) 0.2028(4) 0.44205(12) 0.0122(7) Uani 1 d . . . C1 C 0.1916(5) 0.0064(4) 0.39129(15) 0.0110(8) Uani 1 d . . . C2 C 0.2192(5) -0.0564(5) 0.34024(15) 0.0147(9) Uani 1 d . . . H2 H 0.2865 -0.1444 0.3392 0.018 Uiso 1 calc R . . C3 C 0.1485(5) 0.0100(4) 0.29174(15) 0.0114(8) Uani 1 d . . . C4 C 0.0468(5) 0.1431(5) 0.29332(15) 0.0146(9) Uani 1 d . . . H4 H -0.0001 0.1889 0.2607 0.018 Uiso 1 calc R . . C5 C 0.0163(5) 0.2054(4) 0.34197(15) 0.0149(9) Uani 1 d . . . H5 H -0.0522 0.2928 0.3424 0.018 Uiso 1 calc R . . C6 C 0.0878(5) 0.1387(4) 0.39177(15) 0.0113(8) Uani 1 d . . . C7 C 0.1417(5) 0.1542(4) 0.49031(15) 0.0131(9) Uani 1 d . . . C8 C 0.2446(5) 0.0200(4) 0.48928(15) 0.0133(9) Uani 1 d . . . H8 H 0.2999 -0.0173 0.5223 0.016 Uiso 1 calc R . . C9 C 0.2663(5) -0.0564(4) 0.44254(14) 0.0109(8) Uani 1 d . . . C10 C 0.1234(5) 0.2346(5) 0.54004(15) 0.0132(9) Uani 1 d . . . H10 H 0.0649 0.3278 0.5363 0.016 Uiso 1 calc R . . C11 C 0.1814(5) 0.1908(4) 0.59226(15) 0.0123(8) Uani 1 d . . . C12 C 0.1612(5) 0.2699(4) 0.64379(15) 0.0139(9) Uani 1 d . . . C13 C 0.2505(5) 0.1485(4) 0.67444(14) 0.0114(8) Uani 1 d . . . C14 C 0.2761(5) 0.0629(4) 0.62495(15) 0.0112(8) Uani 1 d . . . C15 C 0.3846(5) -0.0073(5) 0.74586(15) 0.0137(9) Uani 1 d . . . H15A H 0.5023 0.0026 0.7372 0.016 Uiso 1 calc R . . H15B H 0.3336 -0.0983 0.7277 0.016 Uiso 1 calc R . . C16 C 0.3824(5) -0.0196(5) 0.80732(15) 0.0157(9) Uani 1 d . . . H16A H 0.4465 -0.1106 0.8204 0.019 Uiso 1 calc R . . H16B H 0.2638 -0.0332 0.8148 0.019 Uiso 1 calc R . . C17 C 0.4585(5) 0.1187(5) 0.83934(15) 0.0143(9) Uani 1 d . . . H17A H 0.5772 0.1326 0.8321 0.017 Uiso 1 calc R . . H17B H 0.3943 0.2099 0.8266 0.017 Uiso 1 calc R . . C18 C 0.4546(6) 0.1026(5) 0.90071(15) 0.0207(10) Uani 1 d . . . H18A H 0.3380 0.0847 0.9080 0.031 Uiso 1 calc R . . H18B H 0.4972 0.1953 0.9187 0.031 Uiso 1 calc R . . H18C H 0.5260 0.0177 0.9142 0.031 Uiso 1 calc R . . C19 C 0.3645(5) -0.2044(4) 0.44367(15) 0.0146(9) Uani 1 d . . . H19A H 0.4050 -0.2308 0.4809 0.022 Uiso 1 calc R . . H19B H 0.4613 -0.1930 0.4232 0.022 Uiso 1 calc R . . H19C H 0.2901 -0.2843 0.4276 0.022 Uiso 1 calc R . . C20 C -0.0771(5) 0.3244(4) 0.43961(15) 0.0139(9) Uani 1 d . . . H20A H -0.1092 0.3416 0.4756 0.021 Uiso 1 calc R . . H20B H -0.1768 0.2928 0.4155 0.021 Uiso 1 calc R . . H20C H -0.0316 0.4177 0.4261 0.021 Uiso 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 0.0250(17) 0.0170(15) 0.0029(13) -0.0014(11) 0.0025(11) 0.0002(12) O2 0.0303(18) 0.0171(15) 0.0075(14) -0.0011(11) 0.0022(12) 0.0079(13) O3 0.0224(16) 0.0189(15) 0.0045(13) 0.0031(11) 0.0008(11) 0.0073(13) O4 0.0236(17) 0.0179(15) 0.0103(14) -0.0037(12) 0.0016(11) 0.0055(13) N1 0.0186(19) 0.0106(17) 0.0078(16) 0.0025(13) 0.0038(13) 0.0005(14) C1 0.011(2) 0.0108(19) 0.0124(19) 0.0001(16) 0.0061(15) -0.0029(16) C2 0.014(2) 0.0115(19) 0.018(2) 0.0016(16) 0.0006(16) 0.0008(16) C3 0.010(2) 0.0120(19) 0.0123(19) -0.0064(16) 0.0026(15) -0.0040(16) C4 0.019(2) 0.014(2) 0.0099(19) 0.0028(16) -0.0024(16) -0.0037(17) C5 0.019(2) 0.011(2) 0.014(2) -0.0010(16) -0.0008(16) 0.0011(17) C6 0.011(2) 0.012(2) 0.011(2) 0.0004(16) 0.0017(15) -0.0059(16) C7 0.020(2) 0.015(2) 0.0050(18) 0.0006(16) 0.0047(15) -0.0042(17) C8 0.021(2) 0.012(2) 0.0065(18) 0.0042(15) 0.0002(15) -0.0028(16) C9 0.014(2) 0.0143(19) 0.0052(18) 0.0021(15) 0.0039(14) -0.0019(16) C10 0.017(2) 0.011(2) 0.0113(19) -0.0037(16) 0.0024(15) 0.0038(16) C11 0.014(2) 0.012(2) 0.0114(19) -0.0029(16) 0.0025(15) -0.0015(16) C12 0.016(2) 0.014(2) 0.012(2) -0.0017(16) -0.0002(16) 0.0003(17) C13 0.013(2) 0.016(2) 0.0048(18) -0.0023(15) 0.0001(14) -0.0013(16) C14 0.008(2) 0.013(2) 0.013(2) -0.0028(16) 0.0037(15) -0.0027(16) C15 0.016(2) 0.016(2) 0.0090(19) 0.0016(16) 0.0015(15) 0.0030(17) C16 0.016(2) 0.016(2) 0.015(2) 0.0006(17) 0.0002(16) 0.0002(17) C17 0.014(2) 0.019(2) 0.0094(19) 0.0029(16) -0.0005(15) 0.0004(17) C18 0.033(3) 0.016(2) 0.012(2) 0.0010(17) 0.0010(18) -0.0026(19) C19 0.019(2) 0.016(2) 0.0091(19) 0.0050(16) 0.0041(16) 0.0036(17) C20 0.020(2) 0.014(2) 0.0081(19) -0.0013(16) 0.0037(15) 0.0061(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 O1 C3 1.349(4) . ? O1 H1 0.8200 . ? O2 C12 1.245(5) . ? O3 C13 1.316(4) . ? O3 C15 1.459(5) . ? O4 C14 1.224(5) . ? N1 C7 1.357(5) . ? N1 C6 1.404(5) . ? N1 C20 1.477(5) . ? C1 C2 1.408(5) . ? C1 C6 1.408(5) . ? C1 C9 1.431(5) . ? C2 C3 1.379(5) . ? C2 H2 0.9300 . ? C3 C4 1.406(6) . ? C4 C5 1.359(5) . ? C4 H4 0.9300 . ? C5 C6 1.408(5) . ? C5 H5 0.9300 . ? C7 C8 1.419(6) . ? C7 C10 1.430(5) . ? C8 C9 1.355(5) . ? C8 H8 0.9300 . ? C9 C19 1.496(5) . ? C10 C11 1.363(5) . ? C10 H10 0.9300 . ? C11 C12 1.466(5) . ? C11 C14 1.512(5) . ? C12 C13 1.429(5) . ? C13 C14 1.460(5) . ? C15 C16 1.516(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.519(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.518(5) . ? 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 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C3 O1 H1 109.5 . . ? C13 O3 C15 116.4(3) . . ? C7 N1 C6 121.7(3) . . ? C7 N1 C20 121.9(3) . . ? C6 N1 C20 116.4(3) . . ? C2 C1 C6 118.3(3) . . ? C2 C1 C9 123.1(4) . . ? C6 C1 C9 118.6(3) . . ? C3 C2 C1 121.3(4) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? O1 C3 C2 118.8(3) . . ? O1 C3 C4 121.8(3) . . ? C2 C3 C4 119.3(3) . . ? C5 C4 C3 120.7(4) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.5(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? N1 C6 C5 120.5(3) . . ? N1 C6 C1 119.6(3) . . ? C5 C6 C1 119.9(3) . . ? N1 C7 C8 117.5(3) . . ? N1 C7 C10 120.4(4) . . ? C8 C7 C10 122.1(3) . . ? C9 C8 C7 123.2(3) . . ? C9 C8 H8 118.4 . . ? C7 C8 H8 118.4 . . ? C8 C9 C1 118.7(4) . . ? C8 C9 C19 121.4(3) . . ? C1 C9 C19 119.9(3) . . ? C11 C10 C7 127.8(4) . . ? C11 C10 H10 116.1 . . ? C7 C10 H10 116.1 . . ? C10 C11 C12 128.6(4) . . ? C10 C11 C14 142.4(4) . . ? C12 C11 C14 89.0(3) . . ? O2 C12 C13 137.1(4) . . ? O2 C12 C11 132.2(4) . . ? C13 C12 C11 90.7(3) . . ? O3 C13 C12 130.3(3) . . ? O3 C13 C14 137.1(4) . . ? C12 C13 C14 92.5(3) . . ? O4 C14 C13 136.8(4) . . ? O4 C14 C11 135.5(3) . . ? C13 C14 C11 87.7(3) . . ? O3 C15 C16 107.0(3) . . ? O3 C15 H15A 110.3 . . ? C16 C15 H15A 110.3 . . ? O3 C15 H15B 110.3 . . ? C16 C15 H15B 110.3 . . ? H15A C15 H15B 108.6 . . ? C15 C16 C17 114.2(3) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C16 112.8(3) . . ? C18 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? C18 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? 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 . . ? C9 C19 H19A 109.5 . . ? C9 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C9 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 C20 H20A 109.5 . . ? N1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.412 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.076 #===END data_2011parm _database_code_depnum_ccdc_archive 'CCDC 809674' #TrackingRef '- Crystallographic data of compounds 2e and 3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H14 N O4' _chemical_formula_weight 344.33 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 8.6579(12) _cell_length_b 9.1217(12) _cell_length_c 13.0877(18) _cell_angle_alpha 85.292(2) _cell_angle_beta 75.940(2) _cell_angle_gamma 62.358(2) _cell_volume 887.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2918 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 27.18 _exptl_crystal_description Plates _exptl_crystal_colour 'Wine Red' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 358 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9787 _exptl_absorpt_correction_T_max 0.9928 _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6776 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0528 _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 -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3416 _reflns_number_gt 2899 _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 ORTEP _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^)+(0.0740P)^2^+2.2670P] 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 3416 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1192 _refine_ls_R_factor_gt 0.1044 _refine_ls_wR_factor_ref 0.2325 _refine_ls_wR_factor_gt 0.2244 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.8387(4) 0.7407(4) 0.5623(2) 0.0167(7) Uani 1 d . . . O1 O 0.7314(3) 0.2335(3) 0.6339(2) 0.0200(6) Uani 1 d . . . O2 O 0.8359(4) 0.0478(3) 0.8453(2) 0.0258(7) Uani 1 d . . . O3 O 0.9922(4) 0.3111(3) 0.8742(2) 0.0280(7) Uani 1 d . . . O4 O 0.5905(4) 1.1068(3) 0.2227(2) 0.0218(6) Uani 1 d . . . C1 C 0.6646(5) 0.7979(5) 0.4306(3) 0.0176(8) Uani 1 d . . . C2 C 0.5977(5) 0.8904(4) 0.3457(3) 0.0177(8) Uani 1 d . . . H2 H 0.5238 0.8677 0.3156 0.021 Uiso 1 calc R . . C3 C 0.6421(5) 1.0140(5) 0.3075(3) 0.0190(8) Uani 1 d . . . C4 C 0.7427(5) 1.0538(5) 0.3578(3) 0.0198(8) Uani 1 d . . . H4 H 0.7686 1.1404 0.3333 0.024 Uiso 1 calc R . . C5 C 0.8045(5) 0.9690(4) 0.4423(3) 0.0159(8) Uani 1 d . . . H5 H 0.8700 0.9991 0.4752 0.019 Uiso 1 calc R . . C6 C 0.7685(5) 0.8357(4) 0.4792(3) 0.0171(8) Uani 1 d . . . C7 C 0.8058(5) 0.6102(4) 0.5997(3) 0.0156(8) Uani 1 d . . . C8 C 0.6940(5) 0.5765(4) 0.5500(3) 0.0181(8) Uani 1 d . . . H8 H 0.6680 0.4898 0.5740 0.022 Uiso 1 calc R . . C9 C 0.6257(5) 0.6647(5) 0.4704(3) 0.0190(8) Uani 1 d . . . H9 H 0.5530 0.6392 0.4411 0.023 Uiso 1 calc R . . C10 C 0.8735(5) 0.5166(5) 0.6827(3) 0.0193(8) Uani 1 d . . . H10 H 0.9370 0.5505 0.7147 0.023 Uiso 1 calc R . . C11 C 0.8555(5) 0.3767(4) 0.7227(3) 0.0172(8) Uani 1 d . . . C12 C 0.7929(5) 0.2565(4) 0.7011(3) 0.0169(8) Uani 1 d . . . C13 C 0.8440(5) 0.1680(4) 0.7999(3) 0.0179(8) Uani 1 d . . . C14 C 0.9079(5) 0.2867(5) 0.8114(3) 0.0202(8) Uani 1 d . . . C15 C 1.0201(6) 0.2015(5) 0.9648(3) 0.0266(9) Uani 1 d . . . C16 C 0.8591 0.2690 1.0488 0.0222(14) Uani 0.62 d P . . C16A C 0.9520 0.3126 1.0702 0.023(2) Uani 0.38 d P . . C17 C 0.8232 0.4333 1.0941 0.036(2) Uani 0.61 d P . . C17A C 0.7469 0.4255 1.0960 0.045(4) Uani 0.39 d P . . C18 C 0.6614(10) 0.5132(8) 1.1862(6) 0.087(3) Uani 1 d . . . C19 C 0.4806(5) 1.0728(5) 0.1720(3) 0.0233(9) Uani 1 d . . . H19A H 0.3692 1.0915 0.2214 0.028 Uiso 1 calc R . . H19B H 0.5423 0.9584 0.1463 0.028 Uiso 1 calc R . . C20 C 0.4435(6) 1.1868(6) 0.0820(3) 0.0288(10) Uani 1 d . . . H20A H 0.3933 1.2992 0.1073 0.043 Uiso 1 calc R . . H20B H 0.3602 1.1747 0.0508 0.043 Uiso 1 calc R . . H20C H 0.5533 1.1596 0.0300 0.043 Uiso 1 calc R . . C21 C 0.9548(6) 0.7820(5) 0.6062(3) 0.0265(9) Uani 1 d . . . H21A H 0.8877 0.8923 0.6368 0.040 Uiso 1 calc R . . H21B H 1.0542 0.7755 0.5511 0.040 Uiso 1 calc R . . H21C H 0.9987 0.7052 0.6594 0.040 Uiso 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 0.0189(16) 0.0182(16) 0.0175(16) 0.0028(12) -0.0075(13) -0.0109(14) O1 0.0223(14) 0.0207(14) 0.0253(15) 0.0012(11) -0.0111(11) -0.0141(12) O2 0.0327(16) 0.0226(15) 0.0271(15) 0.0098(12) -0.0126(13) -0.0154(13) O3 0.0453(18) 0.0282(15) 0.0266(15) 0.0108(12) -0.0223(14) -0.0250(14) O4 0.0245(15) 0.0244(14) 0.0228(14) 0.0081(11) -0.0114(12) -0.0146(12) C1 0.0150(18) 0.0176(18) 0.0173(19) -0.0009(15) -0.0022(14) -0.0056(15) C2 0.0169(19) 0.0172(18) 0.0214(19) -0.0043(15) -0.0061(15) -0.0082(16) C3 0.0194(19) 0.0203(19) 0.0161(18) 0.0014(15) -0.0027(15) -0.0088(16) C4 0.022(2) 0.0158(18) 0.022(2) 0.0014(15) -0.0017(16) -0.0110(16) C5 0.0180(19) 0.0155(17) 0.0167(18) -0.0004(14) -0.0060(15) -0.0085(15) C6 0.0111(17) 0.0150(18) 0.0200(19) -0.0035(15) 0.0000(14) -0.0028(15) C7 0.0146(18) 0.0127(17) 0.0184(18) -0.0051(14) -0.0003(14) -0.0061(15) C8 0.0161(19) 0.0118(17) 0.025(2) 0.0001(15) -0.0036(15) -0.0055(15) C9 0.0186(19) 0.0194(19) 0.025(2) 0.0012(16) -0.0103(16) -0.0116(16) C10 0.022(2) 0.0193(19) 0.0205(19) -0.0006(15) -0.0079(16) -0.0116(17) C11 0.0142(18) 0.0158(18) 0.0167(18) -0.0050(14) 0.0002(14) -0.0037(15) C12 0.0147(18) 0.0130(17) 0.0213(19) -0.0038(14) -0.0037(15) -0.0046(15) C13 0.0180(19) 0.0166(18) 0.0158(18) 0.0028(15) -0.0028(15) -0.0061(16) C14 0.021(2) 0.0155(18) 0.023(2) 0.0025(15) -0.0063(16) -0.0072(16) C15 0.037(2) 0.022(2) 0.022(2) 0.0046(17) -0.0126(18) -0.0129(19) C16 0.028(4) 0.019(3) 0.020(3) -0.001(2) -0.005(3) -0.011(3) C16A 0.028(6) 0.020(5) 0.020(5) 0.007(4) -0.012(5) -0.006(5) C17 0.044(6) 0.027(4) 0.025(4) -0.011(3) 0.003(4) -0.009(4) C17A 0.037(9) 0.050(9) 0.036(8) 0.012(7) -0.008(6) -0.012(7) C18 0.084(5) 0.049(4) 0.070(5) -0.014(3) 0.039(4) -0.009(4) C19 0.022(2) 0.026(2) 0.025(2) 0.0015(17) -0.0093(16) -0.0120(18) C20 0.030(2) 0.035(2) 0.024(2) 0.0057(18) -0.0109(18) -0.016(2) C21 0.037(2) 0.031(2) 0.030(2) 0.0134(18) -0.0213(19) -0.026(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 C7 1.374(4) . ? N1 C6 1.408(5) . ? N1 C21 1.466(5) . ? O1 C12 1.209(4) . ? O2 C13 1.226(4) . ? O3 C14 1.315(5) . ? O3 C15 1.478(5) . ? O4 C3 1.372(4) . ? O4 C19 1.434(4) . ? C1 C6 1.391(5) . ? C1 C2 1.410(5) . ? C1 C9 1.433(5) . ? C2 C3 1.373(5) . ? C2 H2 0.9300 . ? C3 C4 1.391(5) . ? C4 C5 1.368(5) . ? C4 H4 0.9300 . ? C5 C6 1.411(5) . ? C5 H5 0.9300 . ? C7 C10 1.395(5) . ? C7 C8 1.439(5) . ? C8 C9 1.342(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.401(5) . ? C10 H10 0.9300 . ? C11 C14 1.408(5) . ? C11 C12 1.501(5) . ? C12 C13 1.515(5) . ? C13 C14 1.457(5) . ? C15 C16 1.449(4) . ? C15 C16A 1.599(4) . ? C16 C17 1.52210(19) . ? C16A C17A 1.5479(2) . ? C17 C18 1.524(6) . ? C19 C20 1.498(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 C7 N1 C6 122.0(3) . . ? C7 N1 C21 120.4(3) . . ? C6 N1 C21 117.6(3) . . ? C14 O3 C15 115.2(3) . . ? C3 O4 C19 117.2(3) . . ? C6 C1 C2 120.6(3) . . ? C6 C1 C9 118.1(3) . . ? C2 C1 C9 121.3(3) . . ? C3 C2 C1 119.7(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? O4 C3 C2 124.5(3) . . ? O4 C3 C4 116.0(3) . . ? C2 C3 C4 119.4(3) . . ? C5 C4 C3 121.7(3) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 N1 120.5(3) . . ? C1 C6 C5 118.7(3) . . ? N1 C6 C5 120.9(3) . . ? N1 C7 C10 122.3(3) . . ? N1 C7 C8 116.5(3) . . ? C10 C7 C8 121.2(3) . . ? C9 C8 C7 122.8(3) . . ? C9 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? C8 C9 C1 120.1(3) . . ? C8 C9 H9 119.9 . . ? C1 C9 H9 119.9 . . ? C7 C10 C11 126.6(3) . . ? C7 C10 H10 116.7 . . ? C11 C10 H10 116.7 . . ? C10 C11 C14 128.7(3) . . ? C10 C11 C12 142.1(3) . . ? C14 C11 C12 89.1(3) . . ? O1 C12 C11 137.0(3) . . ? O1 C12 C13 134.0(3) . . ? C11 C12 C13 89.0(3) . . ? O2 C13 C14 138.4(4) . . ? O2 C13 C12 134.8(3) . . ? C14 C13 C12 86.8(3) . . ? O3 C14 C11 127.8(3) . . ? O3 C14 C13 137.1(3) . . ? C11 C14 C13 95.1(3) . . ? C16 C15 O3 109.0(3) . . ? O3 C15 C16A 108.8(3) . . ? C15 C16 C17 112.18(16) . . ? C17 C16A C15 127.52(15) . . ? C17A C16A C15 112.36(16) . . ? C16 C17 C18 117.1(3) . . ? C18 C17A C16A 121.6(4) . . ? O4 C19 C20 107.6(3) . . ? O4 C19 H19A 110.2 . . ? C20 C19 H19A 110.2 . . ? O4 C19 H19B 110.2 . . ? C20 C19 H19B 110.2 . . ? H19A C19 H19B 108.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N1 C21 H21A 109.5 . . ? N1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.563 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.077