# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Dou, Guolan' 'Shi, DaQing' _publ_contact_author_name 'Dr DaQing Shi' _publ_contact_author_email dqshi@suda.edu.cn _publ_section_title ; One pot Synthesis of Cis-bispyrimidodiazepinone Derivatives via Low-valent Titanium Reagent (TiCl4/Sm) ; # Attachment '091104b.cif' data_091104b _database_code_depnum_ccdc_archive 'CCDC 826748' #TrackingRef '091104b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 N2 O6' _chemical_formula_weight 396.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.7115(11) _cell_length_b 14.9304(15) _cell_length_c 11.9095(12) _cell_angle_alpha 90.00 _cell_angle_beta 118.0980(10) _cell_angle_gamma 90.00 _cell_volume 1837.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1613 _cell_measurement_theta_min 2.371 _cell_measurement_theta_max 22.385 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9587 _exptl_absorpt_correction_T_max 0.9842 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 9123 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3229 _reflns_number_gt 1771 _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^)+(0.0343P)^2^+0.0054P] 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 3229 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1054 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _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 0.51412(19) 0.20456(12) 0.52010(19) 0.0342(5) Uani 1 1 d . . . N2 N 0.65340(19) 0.30419(12) 0.43974(19) 0.0354(5) Uani 1 1 d . . . O1 O 0.67159(17) 0.13041(11) 0.69669(15) 0.0487(5) Uani 1 1 d . . . O2 O 0.56701(19) 0.24344(12) 0.72274(18) 0.0585(6) Uani 1 1 d . . . O3 O 0.73187(18) -0.13636(11) 0.4126(2) 0.0584(6) Uani 1 1 d . . . O4 O 0.84972(17) 0.23215(12) 0.54314(17) 0.0499(5) Uani 1 1 d . . . O5 O 0.82022(19) 0.36068(13) 0.61945(19) 0.0658(6) Uani 1 1 d . . . O6 O 0.7562(2) 0.06729(14) 0.0947(2) 0.0715(6) Uani 1 1 d . . . C1 C 0.4212(2) 0.27937(15) 0.4718(3) 0.0446(7) Uani 1 1 d . . . H1A H 0.3686 0.2792 0.5149 0.053 Uiso 1 1 calc R . . H1B H 0.3641 0.2707 0.3816 0.053 Uiso 1 1 calc R . . C2 C 0.4879(3) 0.36930(16) 0.4919(3) 0.0491(8) Uani 1 1 d . . . H2A H 0.4228 0.4161 0.4641 0.059 Uiso 1 1 calc R . . H2B H 0.5445 0.3776 0.5822 0.059 Uiso 1 1 calc R . . C3 C 0.5668(3) 0.38018(16) 0.4221(3) 0.0474(8) Uani 1 1 d . . . H3A H 0.5083 0.3874 0.3319 0.057 Uiso 1 1 calc R . . H3B H 0.6181 0.4344 0.4517 0.057 Uiso 1 1 calc R . . C4 C 0.5808(3) 0.19689(17) 0.6474(3) 0.0403(7) Uani 1 1 d . . . C5 C 0.5406(2) 0.15700(15) 0.4278(2) 0.0307(6) Uani 1 1 d . . . H5 H 0.4571 0.1359 0.3605 0.037 Uiso 1 1 calc R . . C6 C 0.6205(2) 0.07533(15) 0.4886(2) 0.0301(6) Uani 1 1 d . . . C7 C 0.6325(2) 0.00646(16) 0.4160(2) 0.0378(7) Uani 1 1 d . . . H7 H 0.5892 0.0102 0.3276 0.045 Uiso 1 1 calc R . . C8 C 0.7084(2) -0.06749(17) 0.4746(3) 0.0409(7) Uani 1 1 d . . . C9 C 0.7658(2) -0.07630(18) 0.6055(3) 0.0467(8) Uani 1 1 d . . . H9 H 0.8144 -0.1270 0.6447 0.056 Uiso 1 1 calc R . . C10 C 0.7510(2) -0.01023(17) 0.6771(3) 0.0449(7) Uani 1 1 d . . . H10 H 0.7882 -0.0161 0.7651 0.054 Uiso 1 1 calc R . . C11 C 0.6801(2) 0.06528(16) 0.6177(2) 0.0348(6) Uani 1 1 d . . . C12 C 0.6859(3) -0.12827(19) 0.2803(3) 0.0767(11) Uani 1 1 d . . . H12A H 0.5930 -0.1254 0.2380 0.115 Uiso 1 1 calc R . . H12B H 0.7132 -0.1792 0.2500 0.115 Uiso 1 1 calc R . . H12C H 0.7200 -0.0746 0.2630 0.115 Uiso 1 1 calc R . . C13 C 0.7736(3) 0.30426(19) 0.5372(3) 0.0446(7) Uani 1 1 d . . . C14 C 0.5970(2) 0.22416(15) 0.3628(2) 0.0327(6) Uani 1 1 d . . . H14 H 0.5248 0.2436 0.2819 0.039 Uiso 1 1 calc R . . C15 C 0.6967(2) 0.18412(15) 0.3341(2) 0.0328(6) Uani 1 1 d . . . C16 C 0.6706(2) 0.14545(15) 0.2189(2) 0.0385(7) Uani 1 1 d . . . H16 H 0.5865 0.1449 0.1520 0.046 Uiso 1 1 calc R . . C17 C 0.7708(3) 0.10740(17) 0.2039(3) 0.0460(7) Uani 1 1 d . . . C18 C 0.8945(3) 0.10810(19) 0.3044(3) 0.0588(9) Uani 1 1 d . . . H18 H 0.9609 0.0805 0.2953 0.071 Uiso 1 1 calc R . . C19 C 0.9218(3) 0.14871(19) 0.4177(3) 0.0545(8) Uani 1 1 d . . . H19 H 1.0059 0.1502 0.4845 0.065 Uiso 1 1 calc R . . C20 C 0.8214(2) 0.18708(16) 0.4296(3) 0.0389(7) Uani 1 1 d . . . C21 C 0.6399(3) 0.0824(2) -0.0188(3) 0.0773(10) Uani 1 1 d . . . H21A H 0.5688 0.0567 -0.0110 0.116 Uiso 1 1 calc R . . H21B H 0.6456 0.0550 -0.0889 0.116 Uiso 1 1 calc R . . H21C H 0.6263 0.1456 -0.0335 0.116 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 0.0337(12) 0.0368(12) 0.0307(13) -0.0006(10) 0.0142(11) 0.0013(10) N2 0.0338(13) 0.0325(12) 0.0342(13) -0.0020(10) 0.0111(11) -0.0022(10) O1 0.0569(12) 0.0484(11) 0.0307(11) -0.0017(9) 0.0123(10) 0.0073(10) O2 0.0772(15) 0.0596(13) 0.0463(13) -0.0137(11) 0.0354(12) -0.0006(11) O3 0.0733(14) 0.0412(11) 0.0648(15) -0.0038(11) 0.0357(12) 0.0104(10) O4 0.0369(11) 0.0575(12) 0.0419(12) -0.0018(10) 0.0074(9) 0.0024(10) O5 0.0654(15) 0.0635(13) 0.0496(14) -0.0211(11) 0.0115(11) -0.0126(11) O6 0.0764(16) 0.0899(16) 0.0601(16) -0.0100(13) 0.0419(14) 0.0154(13) C1 0.0406(16) 0.0417(16) 0.0517(18) -0.0015(14) 0.0220(14) 0.0049(14) C2 0.0502(18) 0.0398(16) 0.054(2) -0.0020(14) 0.0222(16) 0.0072(14) C3 0.0534(18) 0.0341(15) 0.051(2) 0.0030(14) 0.0216(16) 0.0037(14) C4 0.0461(18) 0.0393(16) 0.0358(18) -0.0057(14) 0.0196(15) -0.0039(14) C5 0.0251(14) 0.0343(14) 0.0281(15) -0.0021(12) 0.0087(12) -0.0010(11) C6 0.0268(14) 0.0292(14) 0.0329(16) 0.0000(12) 0.0129(12) -0.0038(11) C7 0.0405(16) 0.0356(15) 0.0352(17) 0.0027(13) 0.0160(14) -0.0004(13) C8 0.0409(17) 0.0320(15) 0.052(2) -0.0042(15) 0.0242(15) -0.0030(13) C9 0.0383(17) 0.0376(16) 0.056(2) 0.0079(16) 0.0155(15) 0.0017(13) C10 0.0430(17) 0.0442(17) 0.0374(18) 0.0063(14) 0.0107(14) -0.0025(14) C11 0.0348(15) 0.0339(14) 0.0329(17) -0.0002(13) 0.0135(13) -0.0045(12) C12 0.110(3) 0.057(2) 0.076(3) -0.008(2) 0.055(2) 0.012(2) C13 0.0438(18) 0.0467(18) 0.0404(19) 0.0033(15) 0.0174(16) -0.0045(15) C14 0.0299(15) 0.0375(14) 0.0265(14) 0.0004(12) 0.0098(12) 0.0004(12) C15 0.0298(15) 0.0365(14) 0.0338(16) 0.0063(13) 0.0163(14) 0.0001(12) C16 0.0364(16) 0.0426(15) 0.0344(17) 0.0038(13) 0.0151(14) 0.0002(13) C17 0.050(2) 0.0505(18) 0.046(2) 0.0006(15) 0.0306(17) 0.0027(15) C18 0.046(2) 0.068(2) 0.072(2) -0.0011(18) 0.0353(19) 0.0095(16) C19 0.0297(17) 0.070(2) 0.056(2) 0.0029(17) 0.0138(16) 0.0033(15) C20 0.0336(17) 0.0440(16) 0.0377(18) 0.0030(14) 0.0158(14) 0.0014(13) C21 0.086(3) 0.101(3) 0.051(2) -0.016(2) 0.037(2) -0.003(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 C4 1.344(3) . ? N1 C5 1.460(3) . ? N1 C1 1.474(3) . ? N2 C13 1.338(3) . ? N2 C14 1.461(3) . ? N2 C3 1.470(3) . ? O1 C4 1.368(3) . ? O1 C11 1.388(3) . ? O2 C4 1.205(3) . ? O3 C8 1.367(3) . ? O3 C12 1.410(3) . ? O4 C13 1.378(3) . ? O4 C20 1.403(3) . ? O5 C13 1.209(3) . ? O6 C17 1.367(3) . ? O6 C21 1.414(3) . ? C1 C2 1.515(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.514(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C6 1.500(3) . ? C5 C14 1.588(3) . ? C5 H5 0.9800 . ? C6 C11 1.365(3) . ? C6 C7 1.393(3) . ? C7 C8 1.383(3) . ? C7 H7 0.9300 . ? C8 C9 1.383(3) . ? C9 C10 1.368(3) . ? C9 H9 0.9300 . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C14 C15 1.488(3) . ? C14 H14 0.9800 . ? C15 C20 1.365(3) . ? C15 C16 1.383(3) . ? C16 C17 1.389(3) . ? C16 H16 0.9300 . ? C17 C18 1.378(4) . ? C18 C19 1.372(4) . ? C18 H18 0.9300 . ? C19 C20 1.374(3) . ? C19 H19 0.9300 . ? 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 C4 N1 C5 126.2(2) . . ? C4 N1 C1 115.8(2) . . ? C5 N1 C1 117.0(2) . . ? C13 N2 C14 121.7(2) . . ? C13 N2 C3 119.8(2) . . ? C14 N2 C3 117.66(19) . . ? C4 O1 C11 120.4(2) . . ? C8 O3 C12 118.1(2) . . ? C13 O4 C20 118.2(2) . . ? C17 O6 C21 118.2(2) . . ? N1 C1 C2 112.3(2) . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C3 C2 C1 114.3(2) . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N2 C3 C2 113.4(2) . . ? N2 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? N2 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? O2 C4 N1 125.5(3) . . ? O2 C4 O1 116.6(2) . . ? N1 C4 O1 117.9(2) . . ? N1 C5 C6 109.70(19) . . ? N1 C5 C14 110.16(17) . . ? C6 C5 C14 116.13(19) . . ? N1 C5 H5 106.8 . . ? C6 C5 H5 106.8 . . ? C14 C5 H5 106.8 . . ? C11 C6 C7 118.1(2) . . ? C11 C6 C5 120.4(2) . . ? C7 C6 C5 121.5(2) . . ? C8 C7 C6 120.3(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? O3 C8 C9 115.0(2) . . ? O3 C8 C7 125.0(3) . . ? C9 C8 C7 120.0(3) . . ? C10 C9 C8 119.8(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 119.4(3) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C6 C11 C10 122.1(3) . . ? C6 C11 O1 121.6(2) . . ? C10 C11 O1 116.3(2) . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 N2 126.3(3) . . ? O5 C13 O4 117.9(3) . . ? N2 C13 O4 115.8(2) . . ? N2 C14 C15 107.52(19) . . ? N2 C14 C5 112.32(19) . . ? C15 C14 C5 114.21(18) . . ? N2 C14 H14 107.5 . . ? C15 C14 H14 107.5 . . ? C5 C14 H14 107.5 . . ? C20 C15 C16 119.4(2) . . ? C20 C15 C14 116.3(2) . . ? C16 C15 C14 124.4(2) . . ? C15 C16 C17 119.5(2) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? O6 C17 C18 116.0(3) . . ? O6 C17 C16 124.5(3) . . ? C18 C17 C16 119.4(3) . . ? C19 C18 C17 121.3(3) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 118.1(3) . . ? C18 C19 H19 120.9 . . ? C20 C19 H19 120.9 . . ? C15 C20 C19 122.1(3) . . ? C15 C20 O4 119.6(2) . . ? C19 C20 O4 118.3(2) . . ? O6 C21 H21A 109.5 . . ? O6 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O6 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 72.6(3) . . . . ? C5 N1 C1 C2 -97.0(3) . . . . ? N1 C1 C2 C3 62.5(3) . . . . ? C13 N2 C3 C2 -89.4(3) . . . . ? C14 N2 C3 C2 80.1(3) . . . . ? C1 C2 C3 N2 -48.4(3) . . . . ? C5 N1 C4 O2 171.4(2) . . . . ? C1 N1 C4 O2 2.9(4) . . . . ? C5 N1 C4 O1 -9.2(4) . . . . ? C1 N1 C4 O1 -177.7(2) . . . . ? C11 O1 C4 O2 170.0(2) . . . . ? C11 O1 C4 N1 -9.4(3) . . . . ? C4 N1 C5 C6 20.1(3) . . . . ? C1 N1 C5 C6 -171.50(19) . . . . ? C4 N1 C5 C14 -108.9(2) . . . . ? C1 N1 C5 C14 59.5(2) . . . . ? N1 C5 C6 C11 -14.0(3) . . . . ? C14 C5 C6 C11 111.7(3) . . . . ? N1 C5 C6 C7 163.6(2) . . . . ? C14 C5 C6 C7 -70.7(3) . . . . ? C11 C6 C7 C8 -3.3(3) . . . . ? C5 C6 C7 C8 179.0(2) . . . . ? C12 O3 C8 C9 -174.6(2) . . . . ? C12 O3 C8 C7 6.3(4) . . . . ? C6 C7 C8 O3 -176.5(2) . . . . ? C6 C7 C8 C9 4.4(4) . . . . ? O3 C8 C9 C10 178.6(2) . . . . ? C7 C8 C9 C10 -2.3(4) . . . . ? C8 C9 C10 C11 -0.9(4) . . . . ? C7 C6 C11 C10 0.1(4) . . . . ? C5 C6 C11 C10 177.8(2) . . . . ? C7 C6 C11 O1 -179.3(2) . . . . ? C5 C6 C11 O1 -1.5(3) . . . . ? C9 C10 C11 C6 2.1(4) . . . . ? C9 C10 C11 O1 -178.6(2) . . . . ? C4 O1 C11 C6 14.6(3) . . . . ? C4 O1 C11 C10 -164.7(2) . . . . ? C14 N2 C13 O5 -165.8(3) . . . . ? C3 N2 C13 O5 3.1(4) . . . . ? C14 N2 C13 O4 13.7(3) . . . . ? C3 N2 C13 O4 -177.3(2) . . . . ? C20 O4 C13 O5 -154.8(2) . . . . ? C20 O4 C13 N2 25.6(3) . . . . ? C13 N2 C14 C15 -44.7(3) . . . . ? C3 N2 C14 C15 146.1(2) . . . . ? C13 N2 C14 C5 81.8(3) . . . . ? C3 N2 C14 C5 -87.4(2) . . . . ? N1 C5 C14 N2 21.5(2) . . . . ? C6 C5 C14 N2 -103.9(2) . . . . ? N1 C5 C14 C15 144.3(2) . . . . ? C6 C5 C14 C15 18.9(3) . . . . ? N2 C14 C15 C20 38.2(3) . . . . ? C5 C14 C15 C20 -87.2(3) . . . . ? N2 C14 C15 C16 -141.7(2) . . . . ? C5 C14 C15 C16 93.0(3) . . . . ? C20 C15 C16 C17 2.3(3) . . . . ? C14 C15 C16 C17 -177.9(2) . . . . ? C21 O6 C17 C18 -165.7(3) . . . . ? C21 O6 C17 C16 15.0(4) . . . . ? C15 C16 C17 O6 179.9(2) . . . . ? C15 C16 C17 C18 0.6(4) . . . . ? O6 C17 C18 C19 178.1(2) . . . . ? C16 C17 C18 C19 -2.6(4) . . . . ? C17 C18 C19 C20 1.6(4) . . . . ? C16 C15 C20 C19 -3.4(4) . . . . ? C14 C15 C20 C19 176.8(2) . . . . ? C16 C15 C20 O4 175.2(2) . . . . ? C14 C15 C20 O4 -4.6(3) . . . . ? C18 C19 C20 C15 1.4(4) . . . . ? C18 C19 C20 O4 -177.2(2) . . . . ? C13 O4 C20 C15 -30.3(3) . . . . ? C13 O4 C20 C19 148.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.188 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.046