# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full MedChemComm _journal_coden_cambridge 1476 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email manojitpal@rediffmail.com _publ_contact_author_name 'Manojit Pal' _publ_author_name 'Manojit Pal' data_ils_drl_07_1 _database_code_depnum_ccdc_archive 'CCDC 832934' #TrackingRef 'BPPC2-07.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 N2 O2' _chemical_formula_weight 436.22 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 ? 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 15.2480(13) _cell_length_b 12.5719(10) _cell_length_c 14.0243(12) _cell_angle_alpha 90.00 _cell_angle_beta 115.645(3) _cell_angle_gamma 90.00 _cell_volume 2423.6(4) _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 ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 916 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 14662 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 22.94 _reflns_number_total 3278 _reflns_number_gt 2433 _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^)+(0.1000P)^2^+0.1739P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3278 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1569 _refine_ls_R_factor_gt 0.1304 _refine_ls_wR_factor_ref 0.3845 _refine_ls_wR_factor_gt 0.3633 _refine_ls_goodness_of_fit_ref 2.591 _refine_ls_restrained_S_all 2.591 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N3 N 0.1784(3) -0.0400(3) 0.0650(3) 0.0673(12) Uani 1 1 d . . . N2 N 0.1118(3) -0.0514(4) -0.0350(4) 0.0834(9) Uani 1 1 d . . . C18 C 0.3335(4) 0.1549(5) 0.3885(4) 0.0849(9) Uani 1 1 d . . . C15 C 0.1690(3) 0.0612(4) 0.0879(4) 0.0623(13) Uani 1 1 d . . . C17 C 0.2781(4) 0.1258(4) 0.2801(4) 0.0655(13) Uani 1 1 d . . . C16 C 0.2313(4) 0.0984(4) 0.1946(5) 0.0685(14) Uani 1 1 d . . . O2 O 0.1106(3) 0.2764(3) 0.0864(3) 0.1005(14) Uani 1 1 d . . . N1 N -0.0112(3) 0.0452(4) -0.1789(3) 0.0834(9) Uani 1 1 d . . . C11 C 0.0973(4) 0.1150(4) 0.0024(4) 0.0679(14) Uani 1 1 d . . . C19 C 0.2908(4) 0.2018(5) 0.4465(4) 0.0849(9) Uani 1 1 d . . . H19 H 0.2253 0.2199 0.4134 0.102 Uiso 1 1 calc R . . C4 C 0.0601(4) 0.0413(5) -0.0769(4) 0.0834(9) Uani 1 1 d . . . C12 C 0.0690(4) 0.2281(5) -0.0051(5) 0.0815(16) Uani 1 1 d . . . C3 C 0.0966(4) -0.1453(5) -0.0939(4) 0.0834(9) Uani 1 1 d . . . C23 C 0.4321(4) 0.1314(5) 0.4397(4) 0.0849(9) Uani 1 1 d . . . H23 H 0.4634 0.1006 0.4026 0.102 Uiso 1 1 calc R . . C5 C 0.1585(5) -0.2380(6) -0.0512(7) 0.1160(12) Uani 1 1 d . . . C21 C 0.4397(4) 0.1993(5) 0.6026(4) 0.0849(9) Uani 1 1 d . . . C20 C 0.3440(4) 0.2225(5) 0.5537(4) 0.0849(9) Uani 1 1 d . . . H20 H 0.3134 0.2526 0.5920 0.102 Uiso 1 1 calc R . . O1 O 0.0142(4) 0.2723(4) -0.0835(4) 0.1256(18) Uani 1 1 d . . . C2 C 0.0249(4) -0.1360(5) -0.1941(4) 0.0834(9) Uani 1 1 d . . . H2 H 0.0098 -0.1944 -0.2391 0.100 Uiso 1 1 calc R . . C22 C 0.4830(4) 0.1538(5) 0.5452(4) 0.0849(9) Uani 1 1 d . . . H22 H 0.5490 0.1377 0.5788 0.102 Uiso 1 1 calc R . . C10 C 0.1935(5) -0.2713(6) 0.0566(7) 0.1160(12) Uani 1 1 d . . . H10 H 0.1769 -0.2349 0.1043 0.139 Uiso 1 1 calc R . . C24 C 0.4966(7) 0.2123(9) 0.7206(7) 0.1558(17) Uani 1 1 d . . . H24A H 0.4609 0.2599 0.7455 0.187 Uiso 1 1 calc R . . H24B H 0.5581 0.2462 0.7346 0.187 Uiso 1 1 calc R . . C1 C -0.0257(4) -0.0430(5) -0.2309(5) 0.0834(9) Uani 1 1 d . . . H1 H -0.0750 -0.0436 -0.2995 0.100 Uiso 1 1 calc R . . C13 C 0.0903(7) 0.3882(6) 0.0908(7) 0.138(2) Uani 1 1 d . . . H13A H 0.1050 0.4278 0.0401 0.166 Uiso 1 1 calc R . . H13B H 0.0221 0.3985 0.0739 0.166 Uiso 1 1 calc R . . C25 C 0.5174(7) 0.1093(9) 0.7850(7) 0.1558(17) Uani 1 1 d . . . H25A H 0.4556 0.0754 0.7694 0.187 Uiso 1 1 calc R . . H25B H 0.5533 0.0623 0.7597 0.187 Uiso 1 1 calc R . . C9 C 0.2523(5) -0.3588(5) 0.0864(7) 0.1160(12) Uani 1 1 d . . . H9 H 0.2782 -0.3801 0.1567 0.139 Uiso 1 1 calc R . . C6 C 0.1824(5) -0.2978(5) -0.1223(7) 0.1160(12) Uani 1 1 d . . . H6 H 0.1602 -0.2779 -0.1928 0.139 Uiso 1 1 calc R . . C7 C 0.2398(5) -0.3869(6) -0.0828(7) 0.1160(12) Uani 1 1 d . . . H7 H 0.2547 -0.4282 -0.1287 0.139 Uiso 1 1 calc R . . C8 C 0.2746(5) -0.4160(6) 0.0178(7) 0.1160(12) Uani 1 1 d . . . H8 H 0.3144 -0.4756 0.0414 0.139 Uiso 1 1 calc R . . C14 C 0.1503(7) 0.4249(6) 0.1966(8) 0.138(2) Uani 1 1 d . . . H14A H 0.1408 0.3799 0.2465 0.208 Uiso 1 1 calc R . . H14B H 0.1327 0.4966 0.2043 0.208 Uiso 1 1 calc R . . H14C H 0.2174 0.4228 0.2093 0.208 Uiso 1 1 calc R . . C27 C 0.6008(7) 0.0160(10) 0.9543(7) 0.1558(17) Uani 1 1 d . . . H27A H 0.6407 -0.0215 0.9270 0.187 Uiso 1 1 calc R . . H27B H 0.5431 -0.0264 0.9393 0.187 Uiso 1 1 calc R . . C26 C 0.5730(7) 0.1173(10) 0.9033(7) 0.1558(17) Uani 1 1 d . . . H26A H 0.6311 0.1596 0.9202 0.187 Uiso 1 1 calc R . . H26B H 0.5332 0.1541 0.9312 0.187 Uiso 1 1 calc R . . C28 C 0.6570(7) 0.0305(9) 1.0723(7) 0.1558(17) Uani 1 1 d . . . H28A H 0.7189 0.0626 1.0877 0.234 Uiso 1 1 calc R . . H28B H 0.6671 -0.0375 1.1066 0.234 Uiso 1 1 calc R . . H28C H 0.6210 0.0756 1.0977 0.234 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 N3 0.068(3) 0.072(3) 0.057(3) -0.0112(19) 0.022(2) -0.003(2) N2 0.0700(15) 0.114(2) 0.0675(15) -0.0167(11) 0.0313(12) -0.0097(12) C18 0.0870(16) 0.0881(19) 0.0698(15) -0.0097(12) 0.0247(13) 0.0033(13) C15 0.067(3) 0.067(3) 0.056(3) -0.006(2) 0.029(3) -0.005(2) C17 0.081(3) 0.057(3) 0.056(3) 0.006(2) 0.027(3) -0.004(3) C16 0.087(4) 0.053(3) 0.078(4) 0.003(3) 0.047(3) -0.001(3) O2 0.131(4) 0.064(2) 0.094(3) -0.004(2) 0.038(3) 0.016(2) N1 0.0700(15) 0.114(2) 0.0675(15) -0.0167(11) 0.0313(12) -0.0097(12) C11 0.069(3) 0.078(3) 0.065(3) 0.007(3) 0.036(3) 0.005(3) C19 0.0870(16) 0.0881(19) 0.0698(15) -0.0097(12) 0.0247(13) 0.0033(13) C4 0.0700(15) 0.114(2) 0.0675(15) -0.0167(11) 0.0313(12) -0.0097(12) C12 0.087(4) 0.090(4) 0.079(4) 0.016(4) 0.046(3) 0.006(3) C3 0.0700(15) 0.114(2) 0.0675(15) -0.0167(11) 0.0313(12) -0.0097(12) C23 0.0870(16) 0.0881(19) 0.0698(15) -0.0097(12) 0.0247(13) 0.0033(13) C5 0.110(2) 0.083(2) 0.154(3) -0.037(2) 0.057(2) -0.0195(15) C21 0.0870(16) 0.0881(19) 0.0698(15) -0.0097(12) 0.0247(13) 0.0033(13) C20 0.0870(16) 0.0881(19) 0.0698(15) -0.0097(12) 0.0247(13) 0.0033(13) O1 0.149(4) 0.122(4) 0.094(3) 0.037(3) 0.041(3) 0.046(3) C2 0.0700(15) 0.114(2) 0.0675(15) -0.0167(11) 0.0313(12) -0.0097(12) C22 0.0870(16) 0.0881(19) 0.0698(15) -0.0097(12) 0.0247(13) 0.0033(13) C10 0.110(2) 0.083(2) 0.154(3) -0.037(2) 0.057(2) -0.0195(15) C24 0.130(3) 0.194(5) 0.123(3) 0.009(3) 0.035(3) -0.003(3) C1 0.0700(15) 0.114(2) 0.0675(15) -0.0167(11) 0.0313(12) -0.0097(12) C13 0.165(6) 0.080(4) 0.168(6) -0.003(3) 0.070(5) 0.007(3) C25 0.130(3) 0.194(5) 0.123(3) 0.009(3) 0.035(3) -0.003(3) C9 0.110(2) 0.083(2) 0.154(3) -0.037(2) 0.057(2) -0.0195(15) C6 0.110(2) 0.083(2) 0.154(3) -0.037(2) 0.057(2) -0.0195(15) C7 0.110(2) 0.083(2) 0.154(3) -0.037(2) 0.057(2) -0.0195(15) C8 0.110(2) 0.083(2) 0.154(3) -0.037(2) 0.057(2) -0.0195(15) C14 0.165(6) 0.080(4) 0.168(6) -0.003(3) 0.070(5) 0.007(3) C27 0.130(3) 0.194(5) 0.123(3) 0.009(3) 0.035(3) -0.003(3) C26 0.130(3) 0.194(5) 0.123(3) 0.009(3) 0.035(3) -0.003(3) C28 0.130(3) 0.194(5) 0.123(3) 0.009(3) 0.035(3) -0.003(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 N3 C15 1.334(6) . ? N3 N2 1.337(6) . ? N2 C4 1.388(8) . ? N2 C3 1.400(8) . ? C18 C19 1.376(8) . ? C18 C23 1.388(8) . ? C18 C17 1.430(8) . ? C15 C11 1.398(7) . ? C15 C16 1.459(7) . ? C17 C16 1.152(6) . ? O2 C12 1.308(7) . ? O2 C13 1.447(9) . ? N1 C1 1.293(7) . ? N1 C4 1.372(7) . ? C11 C4 1.368(7) . ? C11 C12 1.476(8) . ? C19 C20 1.389(7) . ? C12 O1 1.193(6) . ? C3 C2 1.362(7) . ? C3 C5 1.455(10) . ? C23 C22 1.369(7) . ? C5 C6 1.417(10) . ? C5 C10 1.431(10) . ? C21 C20 1.350(8) . ? C21 C22 1.368(8) . ? C21 C24 1.508(9) . ? C2 C1 1.372(8) . ? C10 C9 1.365(10) . ? C24 C25 1.530(13) . ? C13 C14 1.441(11) . ? C25 C26 1.505(11) . ? C9 C8 1.357(10) . ? C6 C7 1.381(10) . ? C7 C8 1.326(10) . ? C27 C26 1.432(14) . ? C27 C28 1.509(12) . ? 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 C15 N3 N2 104.1(4) . . ? N3 N2 C4 112.8(5) . . ? N3 N2 C3 124.5(5) . . ? C4 N2 C3 122.6(5) . . ? C19 C18 C23 117.9(5) . . ? C19 C18 C17 121.6(5) . . ? C23 C18 C17 120.4(5) . . ? N3 C15 C11 112.4(4) . . ? N3 C15 C16 117.5(4) . . ? C11 C15 C16 130.1(5) . . ? C16 C17 C18 176.6(5) . . ? C17 C16 C15 177.3(5) . . ? C12 O2 C13 118.1(6) . . ? C1 N1 C4 115.0(5) . . ? C4 C11 C15 105.4(5) . . ? C4 C11 C12 126.1(5) . . ? C15 C11 C12 128.5(5) . . ? C18 C19 C20 121.1(5) . . ? C11 C4 N1 133.3(6) . . ? C11 C4 N2 105.3(5) . . ? N1 C4 N2 121.3(5) . . ? O1 C12 O2 122.4(6) . . ? O1 C12 C11 125.5(6) . . ? O2 C12 C11 112.0(5) . . ? C2 C3 N2 113.0(6) . . ? C2 C3 C5 125.5(6) . . ? N2 C3 C5 121.3(5) . . ? C22 C23 C18 119.8(5) . . ? C6 C5 C10 119.8(7) . . ? C6 C5 C3 117.0(7) . . ? C10 C5 C3 123.2(6) . . ? C20 C21 C22 118.9(5) . . ? C20 C21 C24 121.0(6) . . ? C22 C21 C24 119.8(6) . . ? C21 C20 C19 120.3(5) . . ? C3 C2 C1 122.1(6) . . ? C21 C22 C23 121.9(6) . . ? C9 C10 C5 117.0(7) . . ? C21 C24 C25 115.4(8) . . ? N1 C1 C2 126.0(6) . . ? C14 C13 O2 107.6(7) . . ? C26 C25 C24 117.9(9) . . ? C8 C9 C10 123.0(9) . . ? C7 C6 C5 117.3(8) . . ? C8 C7 C6 122.9(8) . . ? C7 C8 C9 120.0(8) . . ? C26 C27 C28 110.2(9) . . ? C27 C26 C25 113.3(10) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 22.94 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.726 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.064 # Attachment 'BPPC3-03.cif' data_ils_drl_03_1 _database_code_depnum_ccdc_archive 'CCDC 832935' #TrackingRef 'BPPC3-03.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 I N2 O2' _chemical_formula_weight 470.05 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 7.3912(4) _cell_length_b 12.3586(6) _cell_length_c 20.4375(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.331(2) _cell_angle_gamma 90.00 _cell_volume 1861.53(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.742 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 15729 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4043 _reflns_number_gt 3497 _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^)+(0.1000P)^2^+0.3005P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4043 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 0.834 _refine_ls_restrained_S_all 0.834 _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 I1 I 0.29812(2) 0.455177(14) 0.048129(9) 0.04856(11) Uani 1 1 d . . . C20 C 0.2018(4) 0.8954(2) -0.00889(13) 0.0507(6) Uani 1 1 d . . . H20A H 0.1451 0.9301 -0.0478 0.061 Uiso 1 1 calc R . . H20B H 0.2113 0.9484 0.0262 0.061 Uiso 1 1 calc R . . C14 C 0.0781(3) 0.64657(18) 0.09230(11) 0.0338(4) Uani 1 1 d . . . C16 C 0.1854(3) 0.72700(18) 0.05889(11) 0.0367(5) Uani 1 1 d . . . C19 C 0.3892(4) 0.8574(2) -0.02259(14) 0.0575(7) Uani 1 1 d . . . H19A H 0.4589 0.9179 -0.0375 0.069 Uiso 1 1 calc R . . H19B H 0.3802 0.8034 -0.0571 0.069 Uiso 1 1 calc R . . C21 C 0.0841(3) 0.8017(2) 0.01063(12) 0.0447(5) Uani 1 1 d . . . H21A H -0.0220 0.8300 0.0300 0.054 Uiso 1 1 calc R . . H21B H 0.0428 0.7611 -0.0283 0.054 Uiso 1 1 calc R . . C17 C 0.3634(3) 0.7336(2) 0.07289(13) 0.0452(5) Uani 1 1 d . . . H17 H 0.4157 0.6887 0.1056 0.054 Uiso 1 1 calc R . . C18 C 0.4854(4) 0.8091(3) 0.03918(15) 0.0585(7) Uani 1 1 d . . . H18A H 0.5924 0.7701 0.0276 0.070 Uiso 1 1 calc R . . H18B H 0.5247 0.8670 0.0690 0.070 Uiso 1 1 calc R . . O1 O -0.0624(2) 0.69658(13) 0.12200(8) 0.0389(4) Uani 1 1 d . . . O2 O -0.3034(2) 0.69846(14) 0.17960(9) 0.0451(4) Uani 1 1 d . . . C11 C -0.1684(3) 0.52902(19) 0.15791(11) 0.0343(5) Uani 1 1 d . . . C13 C 0.1012(3) 0.53863(17) 0.09570(12) 0.0336(5) Uani 1 1 d . . . C15 C -0.1909(3) 0.64291(18) 0.15585(11) 0.0345(4) Uani 1 1 d . . . C12 C -0.0250(3) 0.47678(18) 0.13045(11) 0.0324(4) Uani 1 1 d . . . C6 C -0.2053(5) 0.0544(2) 0.18799(17) 0.0512(7) Uani 1 1 d . . . H6 H -0.3272 0.0520 0.1964 0.061 Uiso 1 1 calc R . . C7 C -0.1144(5) -0.0405(2) 0.17647(16) 0.0549(7) Uani 1 1 d . . . H7 H -0.1758 -0.1062 0.1766 0.066 Uiso 1 1 calc R . . C5 C -0.1153(3) 0.15456(18) 0.18703(11) 0.0384(5) Uani 1 1 d . . . C9 C 0.1562(4) 0.0581(2) 0.16422(15) 0.0504(6) Uani 1 1 d . . . H9 H 0.2780 0.0591 0.1558 0.060 Uiso 1 1 calc R . . C8 C 0.0654(4) -0.0385(2) 0.16491(15) 0.0500(7) Uani 1 1 d . . . H8 H 0.1261 -0.1028 0.1575 0.060 Uiso 1 1 calc R . . C10 C 0.0684(3) 0.15419(19) 0.17595(12) 0.0438(5) Uani 1 1 d . . . H10 H 0.1324 0.2190 0.1765 0.053 Uiso 1 1 calc R . . N1 N -0.4184(3) 0.44762(16) 0.21905(13) 0.0445(5) Uani 1 1 d . . . C3 C -0.2203(3) 0.25336(19) 0.19873(11) 0.0382(5) Uani 1 1 d . . . C1 C -0.4690(4) 0.3514(2) 0.23983(16) 0.0538(7) Uani 1 1 d . . . H1 H -0.5758 0.3478 0.2611 0.065 Uiso 1 1 calc R . . C2 C -0.3744(4) 0.2551(2) 0.23223(14) 0.0512(6) Uani 1 1 d . . . H2 H -0.4162 0.1914 0.2500 0.061 Uiso 1 1 calc R . . N3 N -0.0221(2) 0.37007(15) 0.13987(9) 0.0367(4) Uani 1 1 d . . . N2 N -0.1703(2) 0.35260(14) 0.17543(9) 0.0344(4) Uani 1 1 d . . . C4 C -0.2654(3) 0.44648(17) 0.18683(12) 0.0352(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.04400(15) 0.04500(15) 0.06043(16) -0.00308(6) 0.02858(10) 0.00368(6) C20 0.0669(16) 0.0390(13) 0.0475(13) 0.0093(11) 0.0124(11) -0.0064(11) C14 0.0300(10) 0.0353(11) 0.0376(10) 0.0013(8) 0.0126(8) -0.0009(8) C16 0.0423(12) 0.0293(11) 0.0397(11) 0.0013(9) 0.0109(9) -0.0032(9) C19 0.0693(18) 0.0497(16) 0.0569(15) 0.0045(12) 0.0262(13) -0.0177(13) C21 0.0481(13) 0.0398(13) 0.0468(13) 0.0091(10) 0.0082(10) -0.0018(10) C17 0.0411(12) 0.0423(13) 0.0526(14) 0.0068(11) 0.0062(10) -0.0081(10) C18 0.0477(14) 0.0516(16) 0.0774(19) 0.0089(14) 0.0126(13) -0.0171(12) O1 0.0423(9) 0.0260(8) 0.0506(9) 0.0019(7) 0.0171(7) 0.0019(6) O2 0.0435(9) 0.0353(9) 0.0592(10) -0.0015(7) 0.0210(7) 0.0083(7) C11 0.0355(11) 0.0329(11) 0.0356(11) -0.0032(8) 0.0089(9) 0.0013(8) C13 0.0319(11) 0.0343(12) 0.0368(11) -0.0007(8) 0.0167(9) 0.0016(8) C15 0.0362(11) 0.0325(11) 0.0355(10) -0.0003(8) 0.0084(8) 0.0012(8) C12 0.0368(11) 0.0275(10) 0.0342(10) -0.0005(8) 0.0123(8) -0.0010(8) C6 0.0618(18) 0.0332(13) 0.0618(17) -0.0010(10) 0.0254(14) -0.0104(10) C7 0.071(2) 0.0326(14) 0.0638(18) -0.0044(11) 0.0250(15) -0.0063(11) C5 0.0520(13) 0.0288(11) 0.0361(11) -0.0003(8) 0.0144(9) -0.0045(9) C9 0.0504(15) 0.0448(14) 0.0568(16) 0.0053(11) 0.0092(12) 0.0044(11) C8 0.0671(19) 0.0346(14) 0.0493(15) 0.0005(10) 0.0110(13) 0.0059(11) C10 0.0498(13) 0.0322(12) 0.0501(13) 0.0041(10) 0.0074(10) -0.0063(10) N1 0.0422(12) 0.0378(12) 0.0573(14) -0.0050(8) 0.0283(10) -0.0044(8) C3 0.0461(13) 0.0310(11) 0.0395(12) -0.0042(9) 0.0177(9) -0.0070(9) C1 0.0522(15) 0.0433(14) 0.0714(18) -0.0047(12) 0.0407(13) -0.0094(11) C2 0.0592(16) 0.0384(13) 0.0600(16) -0.0007(11) 0.0311(13) -0.0121(11) N3 0.0387(9) 0.0296(9) 0.0448(10) -0.0009(8) 0.0227(8) -0.0013(7) N2 0.0395(9) 0.0301(9) 0.0358(9) -0.0025(7) 0.0180(7) -0.0047(7) C4 0.0373(12) 0.0327(12) 0.0376(11) -0.0044(8) 0.0154(9) -0.0024(8) _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 I1 C13 2.084(2) . ? C20 C19 1.508(4) . ? C20 C21 1.520(3) . ? C14 C13 1.346(3) . ? C14 O1 1.387(3) . ? C14 C16 1.472(3) . ? C16 C17 1.328(3) . ? C16 C21 1.508(3) . ? C19 C18 1.523(4) . ? C17 C18 1.501(3) . ? O1 C15 1.385(3) . ? O2 C15 1.208(3) . ? C11 C12 1.395(3) . ? C11 C4 1.403(3) . ? C11 C15 1.417(3) . ? C13 C12 1.435(3) . ? C12 N3 1.333(3) . ? C6 C7 1.381(4) . ? C6 C5 1.407(3) . ? C7 C8 1.367(5) . ? C5 C10 1.393(4) . ? C5 C3 1.476(3) . ? C9 C8 1.371(4) . ? C9 C10 1.382(4) . ? N1 C1 1.326(3) . ? N1 C4 1.351(3) . ? C3 C2 1.373(3) . ? C3 N2 1.376(3) . ? C1 C2 1.395(4) . ? N3 N2 1.376(2) . ? N2 C4 1.385(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 C20 C21 111.3(2) . . ? C13 C14 O1 121.01(19) . . ? C13 C14 C16 128.5(2) . . ? O1 C14 C16 110.47(18) . . ? C17 C16 C14 120.1(2) . . ? C17 C16 C21 122.6(2) . . ? C14 C16 C21 117.3(2) . . ? C20 C19 C18 110.2(2) . . ? C16 C21 C20 111.8(2) . . ? C16 C17 C18 124.0(2) . . ? C17 C18 C19 111.4(2) . . ? C15 O1 C14 124.69(18) . . ? C12 C11 C4 105.1(2) . . ? C12 C11 C15 122.6(2) . . ? C4 C11 C15 132.2(2) . . ? C14 C13 C12 118.0(2) . . ? C14 C13 I1 123.83(17) . . ? C12 C13 I1 118.06(15) . . ? O2 C15 O1 116.6(2) . . ? O2 C15 C11 129.4(2) . . ? O1 C15 C11 114.0(2) . . ? N3 C12 C11 113.8(2) . . ? N3 C12 C13 126.5(2) . . ? C11 C12 C13 119.6(2) . . ? C7 C6 C5 120.5(3) . . ? C8 C7 C6 120.4(3) . . ? C10 C5 C6 117.9(2) . . ? C10 C5 C3 124.1(2) . . ? C6 C5 C3 118.1(2) . . ? C8 C9 C10 120.7(3) . . ? C7 C8 C9 120.0(3) . . ? C9 C10 C5 120.5(2) . . ? C1 N1 C4 114.4(2) . . ? C2 C3 N2 114.4(2) . . ? C2 C3 C5 124.1(2) . . ? N2 C3 C5 121.5(2) . . ? N1 C1 C2 125.0(2) . . ? C3 C2 C1 120.7(2) . . ? C12 N3 N2 103.11(17) . . ? N3 N2 C3 124.60(18) . . ? N3 N2 C4 113.05(18) . . ? C3 N2 C4 122.34(19) . . ? N1 C4 N2 123.0(2) . . ? N1 C4 C11 132.1(2) . . ? N2 C4 C11 104.9(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.614 _refine_diff_density_min -0.736 _refine_diff_density_rms 0.055