# Supplementary Material (ESI) for Chemical Communications # This journal is (c) 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_email zhanghbyd@gmail.com _publ_contact_author_name 'Hongbin Zhang' loop_ _publ_author_name 'Hongbin Zhang' 'Zhongxuan Xu' 'Kun Huang' 'Tong Liu' 'Mingjin Xie' data_101220a_0m _database_code_depnum_ccdc_archive 'CCDC 810808' #TrackingRef '101220A_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H21 N O3' _chemical_formula_sum 'C22 H21 N O3' _chemical_formula_weight 347.40 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 P2(1)/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 8.281(3) _cell_length_b 17.475(6) _cell_length_c 12.655(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.793(4) _cell_angle_gamma 90.00 _cell_volume 1792.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2080 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 21.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9756 _exptl_absorpt_correction_T_max 0.9839 _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 12206 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.65 _reflns_number_total 4219 _reflns_number_gt 2573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _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^)+(0.0465P)^2^+0.3301P] 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 SHELXL _refine_ls_extinction_coef 0.0064(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4219 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.26073(17) 0.19146(9) 0.47167(12) 0.0446(4) Uani 1 1 d . . . O1 O 0.31644(14) 0.29174(7) 0.66882(10) 0.0433(3) Uani 1 1 d . . . O2 O 0.01784(15) 0.24608(9) 0.37313(11) 0.0623(4) Uani 1 1 d . . . O3 O 0.89989(15) 0.28323(9) 0.65199(12) 0.0607(4) Uani 1 1 d . . . H3 H 0.9450 0.2783 0.7156 0.091 Uiso 1 1 calc R . . C1 C 0.40131(19) 0.24321(10) 0.51508(14) 0.0373(4) Uani 1 1 d . . . C2 C 0.5436(2) 0.23056(11) 0.46115(16) 0.0467(5) Uani 1 1 d . . . H2 H 0.5215 0.2233 0.3868 0.056 Uiso 1 1 calc R . . C3 C 0.6985(2) 0.22917(11) 0.51308(16) 0.0493(5) Uani 1 1 d . . . H3A H 0.7804 0.2195 0.4743 0.059 Uiso 1 1 calc R . . C4 C 0.7478(2) 0.24256(11) 0.63176(16) 0.0451(5) Uani 1 1 d . . . H4 H 0.7632 0.1932 0.6692 0.054 Uiso 1 1 calc R . . C5 C 0.6149(2) 0.28742(11) 0.67078(14) 0.0412(4) Uani 1 1 d . . . H5A H 0.6099 0.3388 0.6414 0.049 Uiso 1 1 calc R . . H5B H 0.6427 0.2913 0.7489 0.049 Uiso 1 1 calc R . . C6 C 0.44667(19) 0.24933(10) 0.63668(14) 0.0370(4) Uani 1 1 d . . . H6 H 0.4513 0.1979 0.6680 0.044 Uiso 1 1 calc R . . C7 C 0.2401(2) 0.34307(10) 0.58342(15) 0.0416(5) Uani 1 1 d . . . H7 H 0.1205 0.3394 0.5780 0.050 Uiso 1 1 calc R . . C8 C 0.2775(2) 0.31004(11) 0.47827(15) 0.0416(4) Uani 1 1 d . . . H8 H 0.3089 0.3471 0.4279 0.050 Uiso 1 1 calc R . . C9 C 0.1572(2) 0.24771(11) 0.42861(15) 0.0466(5) Uani 1 1 d . . . C10 C 0.2872(2) 0.42615(10) 0.60575(16) 0.0428(4) Uani 1 1 d . . . C11 C 0.3819(3) 0.45120(12) 0.70142(18) 0.0606(6) Uani 1 1 d . . . H11 H 0.4259 0.4158 0.7544 0.073 Uiso 1 1 calc R . . C12 C 0.4130(3) 0.52841(13) 0.7202(2) 0.0774(8) Uani 1 1 d . . . H12 H 0.4782 0.5442 0.7853 0.093 Uiso 1 1 calc R . . C13 C 0.3489(3) 0.58124(13) 0.6444(2) 0.0717(7) Uani 1 1 d . . . H13 H 0.3701 0.6330 0.6575 0.086 Uiso 1 1 calc R . . C14 C 0.2534(4) 0.55797(13) 0.5488(2) 0.0834(8) Uani 1 1 d . . . H14 H 0.2086 0.5938 0.4966 0.100 Uiso 1 1 calc R . . C15 C 0.2237(3) 0.48084(13) 0.5299(2) 0.0739(7) Uani 1 1 d . . . H15 H 0.1591 0.4654 0.4644 0.089 Uiso 1 1 calc R . . C16 C 0.2512(3) 0.10902(11) 0.46379(17) 0.0561(6) Uani 1 1 d . . . H16A H 0.3587 0.0896 0.4577 0.067 Uiso 1 1 calc R . . H16B H 0.1741 0.0956 0.3978 0.067 Uiso 1 1 calc R . . C17 C 0.1985(2) 0.06902(10) 0.55716(16) 0.0461(5) Uani 1 1 d . . . C18 C 0.1277(2) 0.10755(12) 0.63121(17) 0.0516(5) Uani 1 1 d . . . H18 H 0.1145 0.1604 0.6260 0.062 Uiso 1 1 calc R . . C19 C 0.0762(3) 0.06818(13) 0.71335(19) 0.0655(6) Uani 1 1 d . . . H19 H 0.0285 0.0947 0.7629 0.079 Uiso 1 1 calc R . . C20 C 0.0949(3) -0.00962(15) 0.7220(2) 0.0768(8) Uani 1 1 d . . . H20 H 0.0608 -0.0359 0.7775 0.092 Uiso 1 1 calc R . . C21 C 0.1643(3) -0.04850(14) 0.6484(2) 0.0759(8) Uani 1 1 d . . . H21 H 0.1762 -0.1014 0.6537 0.091 Uiso 1 1 calc R . . C22 C 0.2167(3) -0.00963(12) 0.5665(2) 0.0626(6) Uani 1 1 d . . . H22 H 0.2645 -0.0364 0.5173 0.075 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 0.0379(8) 0.0485(9) 0.0439(10) -0.0012(7) 0.0002(7) -0.0098(7) O1 0.0416(7) 0.0493(8) 0.0412(8) 0.0080(6) 0.0137(6) 0.0040(6) O2 0.0383(7) 0.0894(11) 0.0513(9) -0.0077(8) -0.0092(6) -0.0017(7) O3 0.0333(7) 0.0906(11) 0.0543(10) 0.0059(8) -0.0002(6) -0.0116(7) C1 0.0314(9) 0.0429(10) 0.0358(10) 0.0007(8) 0.0024(7) -0.0065(7) C2 0.0443(11) 0.0600(12) 0.0362(11) -0.0057(9) 0.0091(8) -0.0063(9) C3 0.0402(10) 0.0615(13) 0.0487(13) -0.0073(10) 0.0147(9) -0.0015(9) C4 0.0308(9) 0.0554(12) 0.0476(12) 0.0049(9) 0.0043(8) -0.0028(8) C5 0.0386(10) 0.0528(11) 0.0312(10) -0.0008(8) 0.0042(8) -0.0070(8) C6 0.0341(9) 0.0416(10) 0.0356(10) 0.0041(8) 0.0075(7) -0.0012(8) C7 0.0324(9) 0.0493(11) 0.0424(11) 0.0055(9) 0.0058(8) 0.0005(8) C8 0.0347(9) 0.0495(11) 0.0385(11) 0.0082(9) 0.0025(8) -0.0029(8) C9 0.0387(10) 0.0642(13) 0.0350(11) -0.0006(10) 0.0032(8) -0.0048(9) C10 0.0360(9) 0.0465(11) 0.0448(12) 0.0042(9) 0.0062(8) 0.0007(8) C11 0.0767(15) 0.0507(13) 0.0487(14) 0.0006(10) -0.0003(11) 0.0113(11) C12 0.0943(19) 0.0592(15) 0.0658(17) -0.0145(13) -0.0141(14) 0.0055(13) C13 0.0904(17) 0.0481(13) 0.0714(18) -0.0034(12) 0.0046(14) -0.0066(12) C14 0.120(2) 0.0478(14) 0.0724(19) 0.0124(13) -0.0032(16) -0.0001(14) C15 0.0938(18) 0.0548(14) 0.0587(16) 0.0053(11) -0.0181(13) -0.0035(12) C16 0.0544(12) 0.0532(13) 0.0595(15) -0.0140(10) 0.0091(10) -0.0112(10) C17 0.0362(9) 0.0421(11) 0.0542(13) -0.0043(9) -0.0046(9) -0.0056(8) C18 0.0524(12) 0.0444(11) 0.0567(14) 0.0023(10) 0.0079(10) -0.0037(9) C19 0.0687(15) 0.0688(16) 0.0581(15) 0.0006(12) 0.0106(11) -0.0138(12) C20 0.0893(19) 0.0687(17) 0.0624(17) 0.0138(14) -0.0079(14) -0.0286(14) C21 0.0810(17) 0.0452(13) 0.087(2) 0.0128(14) -0.0169(15) -0.0103(12) C22 0.0540(13) 0.0455(13) 0.0795(17) -0.0084(12) -0.0070(12) 0.0006(10) _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 C9 1.344(2) . ? N1 C16 1.445(2) . ? N1 C1 1.488(2) . ? O1 C6 1.434(2) . ? O1 C7 1.447(2) . ? O2 C9 1.223(2) . ? O3 C4 1.423(2) . ? O3 H3 0.8200 . ? C1 C2 1.494(3) . ? C1 C6 1.511(3) . ? C1 C8 1.561(2) . ? C2 C3 1.317(2) . ? C2 H2 0.9300 . ? C3 C4 1.492(3) . ? C3 H3A 0.9300 . ? C4 C5 1.514(2) . ? C4 H4 0.9800 . ? C5 C6 1.525(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6 0.9800 . ? C7 C10 1.515(3) . ? C7 C8 1.539(3) . ? C7 H7 0.9800 . ? C8 C9 1.522(3) . ? C8 H8 0.9800 . ? C10 C11 1.373(3) . ? C10 C15 1.381(3) . ? C11 C12 1.385(3) . ? C11 H11 0.9300 . ? C12 C13 1.359(3) . ? C12 H12 0.9300 . ? C13 C14 1.365(3) . ? C13 H13 0.9300 . ? C14 C15 1.382(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.512(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.378(3) . ? C17 C22 1.385(3) . ? C18 C19 1.385(3) . ? C18 H18 0.9300 . ? C19 C20 1.370(3) . ? C19 H19 0.9300 . ? C20 C21 1.370(4) . ? C20 H20 0.9300 . ? C21 C22 1.382(3) . ? C21 H21 0.9300 . ? C22 H22 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 N1 C16 132.83(16) . . ? C9 N1 C1 95.23(14) . . ? C16 N1 C1 131.21(15) . . ? C6 O1 C7 110.35(13) . . ? C4 O3 H3 109.5 . . ? N1 C1 C2 111.84(15) . . ? N1 C1 C6 115.58(14) . . ? C2 C1 C6 114.87(14) . . ? N1 C1 C8 85.86(12) . . ? C2 C1 C8 120.37(15) . . ? C6 C1 C8 105.21(14) . . ? C3 C2 C1 123.62(18) . . ? C3 C2 H2 118.2 . . ? C1 C2 H2 118.2 . . ? C2 C3 C4 122.53(17) . . ? C2 C3 H3A 118.7 . . ? C4 C3 H3A 118.7 . . ? O3 C4 C3 108.03(15) . . ? O3 C4 C5 111.00(16) . . ? C3 C4 C5 109.99(15) . . ? O3 C4 H4 109.3 . . ? C3 C4 H4 109.3 . . ? C5 C4 H4 109.3 . . ? C4 C5 C6 111.39(15) . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? O1 C6 C1 106.29(13) . . ? O1 C6 C5 112.99(14) . . ? C1 C6 C5 109.97(14) . . ? O1 C6 H6 109.2 . . ? C1 C6 H6 109.2 . . ? C5 C6 H6 109.2 . . ? O1 C7 C10 113.46(15) . . ? O1 C7 C8 106.19(14) . . ? C10 C7 C8 115.52(15) . . ? O1 C7 H7 107.1 . . ? C10 C7 H7 107.1 . . ? C8 C7 H7 107.1 . . ? C9 C8 C7 113.27(15) . . ? C9 C8 C1 85.54(14) . . ? C7 C8 C1 104.99(14) . . ? C9 C8 H8 116.2 . . ? C7 C8 H8 116.2 . . ? C1 C8 H8 116.2 . . ? O2 C9 N1 131.66(19) . . ? O2 C9 C8 135.63(19) . . ? N1 C9 C8 92.69(14) . . ? C11 C10 C15 117.42(19) . . ? C11 C10 C7 123.31(17) . . ? C15 C10 C7 119.12(18) . . ? C10 C11 C12 121.0(2) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.7(2) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 119.6(2) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C10 C15 C14 121.7(2) . . ? C10 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? N1 C16 C17 115.29(17) . . ? N1 C16 H16A 108.5 . . ? C17 C16 H16A 108.5 . . ? N1 C16 H16B 108.5 . . ? C17 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C18 C17 C22 118.7(2) . . ? C18 C17 C16 122.43(18) . . ? C22 C17 C16 118.8(2) . . ? C17 C18 C19 120.5(2) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C20 C19 C18 120.4(2) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 119.6(2) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C20 C21 C22 120.4(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C17 120.4(2) . . ? C21 C22 H22 119.8 . . ? C17 C22 H22 119.8 . . ? 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 C9 N1 C1 C2 -114.68(16) . . . . ? C16 N1 C1 C2 56.3(3) . . . . ? C9 N1 C1 C6 111.35(16) . . . . ? C16 N1 C1 C6 -77.7(2) . . . . ? C9 N1 C1 C8 6.46(14) . . . . ? C16 N1 C1 C8 177.46(19) . . . . ? N1 C1 C2 C3 -138.19(19) . . . . ? C6 C1 C2 C3 -3.9(3) . . . . ? C8 C1 C2 C3 123.5(2) . . . . ? C1 C2 C3 C4 -1.9(3) . . . . ? C2 C3 C4 O3 -144.22(19) . . . . ? C2 C3 C4 C5 -22.9(3) . . . . ? O3 C4 C5 C6 172.69(15) . . . . ? C3 C4 C5 C6 53.2(2) . . . . ? C7 O1 C6 C1 -28.08(17) . . . . ? C7 O1 C6 C5 92.62(17) . . . . ? N1 C1 C6 O1 -71.18(18) . . . . ? C2 C1 C6 O1 156.24(14) . . . . ? C8 C1 C6 O1 21.53(16) . . . . ? N1 C1 C6 C5 166.19(14) . . . . ? C2 C1 C6 C5 33.6(2) . . . . ? C8 C1 C6 C5 -101.11(15) . . . . ? C4 C5 C6 O1 -177.84(14) . . . . ? C4 C5 C6 C1 -59.3(2) . . . . ? C6 O1 C7 C10 -105.47(16) . . . . ? C6 O1 C7 C8 22.49(17) . . . . ? O1 C7 C8 C9 83.74(17) . . . . ? C10 C7 C8 C9 -149.53(15) . . . . ? O1 C7 C8 C1 -7.84(17) . . . . ? C10 C7 C8 C1 118.89(15) . . . . ? N1 C1 C8 C9 -5.69(13) . . . . ? C2 C1 C8 C9 107.26(17) . . . . ? C6 C1 C8 C9 -121.10(14) . . . . ? N1 C1 C8 C7 107.22(14) . . . . ? C2 C1 C8 C7 -139.83(16) . . . . ? C6 C1 C8 C7 -8.18(17) . . . . ? C16 N1 C9 O2 4.3(4) . . . . ? C1 N1 C9 O2 175.1(2) . . . . ? C16 N1 C9 C8 -177.4(2) . . . . ? C1 N1 C9 C8 -6.61(15) . . . . ? C7 C8 C9 O2 80.1(3) . . . . ? C1 C8 C9 O2 -175.5(2) . . . . ? C7 C8 C9 N1 -98.11(16) . . . . ? C1 C8 C9 N1 6.29(14) . . . . ? O1 C7 C10 C11 -5.2(3) . . . . ? C8 C7 C10 C11 -128.2(2) . . . . ? O1 C7 C10 C15 179.39(18) . . . . ? C8 C7 C10 C15 56.4(2) . . . . ? C15 C10 C11 C12 -0.5(3) . . . . ? C7 C10 C11 C12 -176.0(2) . . . . ? C10 C11 C12 C13 0.6(4) . . . . ? C11 C12 C13 C14 -0.1(4) . . . . ? C12 C13 C14 C15 -0.4(4) . . . . ? C11 C10 C15 C14 0.0(4) . . . . ? C7 C10 C15 C14 175.6(2) . . . . ? C13 C14 C15 C10 0.5(4) . . . . ? C9 N1 C16 C17 -98.9(2) . . . . ? C1 N1 C16 C17 93.4(2) . . . . ? N1 C16 C17 C18 14.6(3) . . . . ? N1 C16 C17 C22 -167.69(17) . . . . ? C22 C17 C18 C19 0.1(3) . . . . ? C16 C17 C18 C19 177.79(18) . . . . ? C17 C18 C19 C20 0.0(3) . . . . ? C18 C19 C20 C21 -0.4(4) . . . . ? C19 C20 C21 C22 0.7(4) . . . . ? C20 C21 C22 C17 -0.5(3) . . . . ? C18 C17 C22 C21 0.2(3) . . . . ? C16 C17 C22 C21 -177.61(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O2 0.82 2.01 2.816(2) 169.0 4_666 _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 28.65 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.210 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.035 # Attachment '110111B.cif' data_110111b _database_code_depnum_ccdc_archive 'CCDC 810809' #TrackingRef '110111B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 N O3' _chemical_formula_weight 309.35 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.406(3) _cell_length_b 11.1729(19) _cell_length_c 19.300(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3322.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1389 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 18.54 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9810 _exptl_absorpt_correction_T_max 0.9867 _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 21667 _diffrn_reflns_av_R_equivalents 0.0947 _diffrn_reflns_av_sigmaI/netI 0.0789 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4022 _reflns_number_gt 1900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _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^)+(0.0551P)^2^+0.6110P] 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 SHELXL _refine_ls_extinction_coef 0.0037(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4022 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1621 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1616 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.18882(13) 0.04490(17) 0.12503(10) 0.0437(5) Uani 1 1 d . . . O1 O 0.33674(11) 0.00596(15) 0.13927(9) 0.0576(5) Uani 1 1 d . . . O2 O -0.10677(13) 0.23363(19) 0.21871(13) 0.0889(8) Uani 1 1 d . . . O3 O 0.26853(14) -0.07651(18) 0.28680(11) 0.0779(7) Uani 1 1 d . . . C1 C -0.03443(18) 0.1937(2) 0.20669(14) 0.0515(7) Uani 1 1 d . . . C2 C 0.03344(17) 0.2693(2) 0.17742(13) 0.0467(6) Uani 1 1 d . . . H2 H 0.0209 0.3486 0.1668 0.056 Uiso 1 1 calc R . . C3 C 0.11223(16) 0.2275(2) 0.16567(12) 0.0419(6) Uani 1 1 d . . . H3 H 0.1530 0.2788 0.1461 0.050 Uiso 1 1 calc R . . C4 C 0.13944(14) 0.10227(19) 0.18211(12) 0.0381(6) Uani 1 1 d . . . C5 C 0.06726(16) 0.0264(2) 0.20971(12) 0.0444(6) Uani 1 1 d . . . H5 H 0.0783 -0.0538 0.2192 0.053 Uiso 1 1 calc R . . C6 C -0.01166(17) 0.0687(2) 0.22122(13) 0.0498(7) Uani 1 1 d . . . H6 H -0.0539 0.0177 0.2390 0.060 Uiso 1 1 calc R . . C7 C 0.22856(14) 0.0961(2) 0.22394(12) 0.0396(6) Uani 1 1 d . . . H7 H 0.2525 0.1759 0.2328 0.048 Uiso 1 1 calc R . . C8 C 0.26607(17) 0.0403(2) 0.15812(13) 0.0438(6) Uani 1 1 d . . . C9 C 0.23007(16) 0.0186(2) 0.28769(13) 0.0466(6) Uani 1 1 d . . . C10 C 0.18189(15) 0.0593(2) 0.35000(13) 0.0460(6) Uani 1 1 d . . . C11 C 0.1571(2) 0.1775(2) 0.35815(14) 0.0648(8) Uani 1 1 d . . . H11 H 0.1700 0.2332 0.3239 0.078 Uiso 1 1 calc R . . C12 C 0.1132(2) 0.2127(3) 0.41697(18) 0.0883(11) Uani 1 1 d . . . H12 H 0.0969 0.2923 0.4225 0.106 Uiso 1 1 calc R . . C13 C 0.0937(2) 0.1304(4) 0.46726(18) 0.0894(11) Uani 1 1 d . . . H13 H 0.0640 0.1543 0.5069 0.107 Uiso 1 1 calc R . . C14 C 0.1177(2) 0.0134(4) 0.45935(16) 0.0793(10) Uani 1 1 d . . . H14 H 0.1040 -0.0420 0.4936 0.095 Uiso 1 1 calc R . . C15 C 0.16202(18) -0.0232(3) 0.40133(14) 0.0617(8) Uani 1 1 d . . . H15 H 0.1786 -0.1028 0.3965 0.074 Uiso 1 1 calc R . . C16 C 0.16402(18) 0.0184(2) 0.05428(13) 0.0546(7) Uani 1 1 d . . . H16A H 0.2160 0.0176 0.0259 0.066 Uiso 1 1 calc R . . H16B H 0.1274 0.0828 0.0376 0.066 Uiso 1 1 calc R . . C17 C 0.11679(19) -0.0981(2) 0.04397(14) 0.0640(8) Uani 1 1 d . . . H17 H 0.0604 -0.0901 0.0670 0.077 Uiso 1 1 calc R . . C18 C 0.0986(2) -0.1170(3) -0.03247(16) 0.0867(11) Uani 1 1 d . . . H18A H 0.1522 -0.1300 -0.0566 0.130 Uiso 1 1 calc R . . H18B H 0.0703 -0.0474 -0.0510 0.130 Uiso 1 1 calc R . . H18C H 0.0616 -0.1854 -0.0382 0.130 Uiso 1 1 calc R . . C19 C 0.1607(2) -0.2030(3) 0.07543(19) 0.0996(13) Uani 1 1 d . . . H19A H 0.1249 -0.2727 0.0699 0.149 Uiso 1 1 calc R . . H19B H 0.1702 -0.1884 0.1239 0.149 Uiso 1 1 calc R . . H19C H 0.2154 -0.2159 0.0529 0.149 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 0.0358(13) 0.0501(12) 0.0451(12) -0.0055(10) 0.0006(10) 0.0012(9) O1 0.0381(11) 0.0667(12) 0.0681(12) 0.0022(10) 0.0069(10) 0.0096(9) O2 0.0461(14) 0.0827(15) 0.138(2) 0.0264(14) 0.0304(13) 0.0204(11) O3 0.0785(16) 0.0636(12) 0.0915(16) 0.0260(11) 0.0169(12) 0.0272(11) C1 0.0381(17) 0.0560(16) 0.0603(17) 0.0070(13) 0.0055(13) 0.0043(13) C2 0.0431(16) 0.0420(13) 0.0549(16) 0.0048(12) 0.0030(13) 0.0051(12) C3 0.0386(16) 0.0416(13) 0.0456(15) 0.0056(11) 0.0003(12) -0.0046(11) C4 0.0309(14) 0.0384(12) 0.0449(14) 0.0030(11) 0.0001(11) -0.0011(10) C5 0.0392(16) 0.0399(13) 0.0541(16) 0.0075(11) -0.0012(12) -0.0040(11) C6 0.0356(17) 0.0537(15) 0.0599(18) 0.0087(13) 0.0038(13) -0.0084(12) C7 0.0327(15) 0.0410(12) 0.0451(15) 0.0009(11) 0.0003(11) -0.0022(11) C8 0.0361(15) 0.0410(13) 0.0544(16) 0.0055(12) 0.0027(13) -0.0016(12) C9 0.0356(15) 0.0481(14) 0.0562(17) 0.0071(13) -0.0069(12) -0.0016(12) C10 0.0430(16) 0.0512(15) 0.0439(15) 0.0047(12) -0.0073(12) -0.0042(12) C11 0.086(2) 0.0580(17) 0.0502(17) -0.0030(14) 0.0050(16) -0.0050(16) C12 0.123(3) 0.075(2) 0.067(2) -0.0138(18) 0.017(2) 0.002(2) C13 0.092(3) 0.119(3) 0.056(2) -0.013(2) 0.0125(18) -0.006(2) C14 0.077(3) 0.105(3) 0.055(2) 0.0175(19) 0.0033(17) -0.010(2) C15 0.0572(19) 0.0710(18) 0.0568(18) 0.0167(15) -0.0039(15) -0.0056(15) C16 0.0598(19) 0.0578(16) 0.0463(16) -0.0009(13) -0.0022(14) 0.0018(14) C17 0.068(2) 0.0630(18) 0.0607(19) -0.0082(14) -0.0205(15) 0.0001(15) C18 0.097(3) 0.092(2) 0.072(2) -0.0211(18) -0.0275(19) 0.004(2) C19 0.132(3) 0.0547(19) 0.112(3) -0.0067(18) -0.055(3) 0.010(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 C8 1.352(3) . ? N1 C16 1.448(3) . ? N1 C4 1.484(3) . ? O1 C8 1.210(3) . ? O2 C1 1.223(3) . ? O3 C9 1.217(3) . ? C1 C2 1.458(3) . ? C1 C6 1.468(3) . ? C2 C3 1.320(3) . ? C2 H2 0.9300 . ? C3 C4 1.495(3) . ? C3 H3 0.9300 . ? C4 C5 1.497(3) . ? C4 C7 1.594(3) . ? C5 C6 1.323(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C9 1.505(3) . ? C7 C8 1.529(3) . ? C7 H7 0.9800 . ? C9 C10 1.485(3) . ? C10 C11 1.383(4) . ? C10 C15 1.388(3) . ? C11 C12 1.378(4) . ? C11 H11 0.9300 . ? C12 C13 1.370(5) . ? C12 H12 0.9300 . ? C13 C14 1.368(5) . ? C13 H13 0.9300 . ? C14 C15 1.373(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.505(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C19 1.483(4) . ? C17 C18 1.517(4) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 C8 N1 C16 132.1(2) . . ? C8 N1 C4 96.71(18) . . ? C16 N1 C4 130.7(2) . . ? O2 C1 C2 121.1(2) . . ? O2 C1 C6 121.9(2) . . ? C2 C1 C6 117.0(2) . . ? C3 C2 C1 121.4(2) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 123.5(2) . . ? C2 C3 H3 118.2 . . ? C4 C3 H3 118.2 . . ? N1 C4 C3 112.98(19) . . ? N1 C4 C5 113.60(19) . . ? C3 C4 C5 113.4(2) . . ? N1 C4 C7 85.18(16) . . ? C3 C4 C7 112.90(18) . . ? C5 C4 C7 115.81(19) . . ? C6 C5 C4 122.7(2) . . ? C6 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C5 C6 C1 121.8(2) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? C9 C7 C8 116.0(2) . . ? C9 C7 C4 116.88(19) . . ? C8 C7 C4 85.54(17) . . ? C9 C7 H7 112.0 . . ? C8 C7 H7 112.0 . . ? C4 C7 H7 112.0 . . ? O1 C8 N1 131.4(2) . . ? O1 C8 C7 136.0(2) . . ? N1 C8 C7 92.54(19) . . ? O3 C9 C10 121.5(2) . . ? O3 C9 C7 119.9(2) . . ? C10 C9 C7 118.6(2) . . ? C11 C10 C15 119.5(3) . . ? C11 C10 C9 121.5(2) . . ? C15 C10 C9 119.0(2) . . ? C12 C11 C10 120.1(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 119.9(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.7(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 119.6(3) . . ? C14 C15 H15 120.2 . . ? C10 C15 H15 120.2 . . ? N1 C16 C17 115.4(2) . . ? N1 C16 H16A 108.4 . . ? C17 C16 H16A 108.4 . . ? N1 C16 H16B 108.4 . . ? C17 C16 H16B 108.4 . . ? H16A C16 H16B 107.5 . . ? C19 C17 C16 114.2(2) . . ? C19 C17 C18 111.9(3) . . ? C16 C17 C18 109.8(2) . . ? C19 C17 H17 106.9 . . ? C16 C17 H17 106.9 . . ? C18 C17 H17 106.9 . . ? 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 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 O2 C1 C2 C3 178.5(3) . . . . ? C6 C1 C2 C3 -1.2(4) . . . . ? C1 C2 C3 C4 -1.2(4) . . . . ? C8 N1 C4 C3 111.6(2) . . . . ? C16 N1 C4 C3 -61.0(3) . . . . ? C8 N1 C4 C5 -117.3(2) . . . . ? C16 N1 C4 C5 70.0(3) . . . . ? C8 N1 C4 C7 -1.23(17) . . . . ? C16 N1 C4 C7 -173.9(2) . . . . ? C2 C3 C4 N1 134.3(2) . . . . ? C2 C3 C4 C5 3.1(3) . . . . ? C2 C3 C4 C7 -131.1(2) . . . . ? N1 C4 C5 C6 -133.8(2) . . . . ? C3 C4 C5 C6 -2.9(3) . . . . ? C7 C4 C5 C6 130.0(2) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? O2 C1 C6 C5 -178.4(3) . . . . ? C2 C1 C6 C5 1.3(4) . . . . ? N1 C4 C7 C9 -115.9(2) . . . . ? C3 C4 C7 C9 131.2(2) . . . . ? C5 C4 C7 C9 -2.0(3) . . . . ? N1 C4 C7 C8 1.08(15) . . . . ? C3 C4 C7 C8 -111.9(2) . . . . ? C5 C4 C7 C8 115.0(2) . . . . ? C16 N1 C8 O1 -4.9(4) . . . . ? C4 N1 C8 O1 -177.4(3) . . . . ? C16 N1 C8 C7 173.8(2) . . . . ? C4 N1 C8 C7 1.28(18) . . . . ? C9 C7 C8 O1 -64.8(4) . . . . ? C4 C7 C8 O1 177.4(3) . . . . ? C9 C7 C8 N1 116.6(2) . . . . ? C4 C7 C8 N1 -1.18(16) . . . . ? C8 C7 C9 O3 8.2(3) . . . . ? C4 C7 C9 O3 106.9(3) . . . . ? C8 C7 C9 C10 -170.1(2) . . . . ? C4 C7 C9 C10 -71.4(3) . . . . ? O3 C9 C10 C11 163.4(3) . . . . ? C7 C9 C10 C11 -18.4(4) . . . . ? O3 C9 C10 C15 -16.1(4) . . . . ? C7 C9 C10 C15 162.1(2) . . . . ? C15 C10 C11 C12 0.3(4) . . . . ? C9 C10 C11 C12 -179.3(3) . . . . ? C10 C11 C12 C13 -0.5(5) . . . . ? C11 C12 C13 C14 0.2(6) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C13 C14 C15 C10 -0.5(5) . . . . ? C11 C10 C15 C14 0.2(4) . . . . ? C9 C10 C15 C14 179.8(2) . . . . ? C8 N1 C16 C17 104.5(3) . . . . ? C4 N1 C16 C17 -85.3(3) . . . . ? N1 C16 C17 C19 -50.9(4) . . . . ? N1 C16 C17 C18 -177.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.210 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.038 # Attachment '110126A.cif' data_110126a _database_code_depnum_ccdc_archive 'CCDC 810810' #TrackingRef '110126A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H25 N O5' _chemical_formula_weight 443.48 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 P2(1)/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 15.443(4) _cell_length_b 12.425(3) _cell_length_c 11.835(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.774(4) _cell_angle_gamma 90.00 _cell_volume 2255.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 695 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 17.86 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9796 _exptl_absorpt_correction_T_max 0.9919 _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 15474 _diffrn_reflns_av_R_equivalents 0.1154 _diffrn_reflns_av_sigmaI/netI 0.1643 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.44 _reflns_number_total 5318 _reflns_number_gt 1659 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _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^)+(0.0596P)^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 SHELXL _refine_ls_extinction_coef 0.0100(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5318 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2356 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1882 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 0.900 _refine_ls_restrained_S_all 0.900 _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 0.1946(2) 0.0785(2) 0.4604(2) 0.0534(8) Uani 1 1 d . . . O5 O 0.56682(17) 0.1912(2) 1.0054(2) 0.0754(9) Uani 1 1 d . . . O3 O 0.26950(17) 0.19570(19) 0.7038(2) 0.0712(8) Uani 1 1 d . . . O2 O 0.33750(18) 0.1061(2) 0.4483(2) 0.0763(9) Uani 1 1 d . . . O1 O 0.2415(2) -0.3590(2) 0.8051(2) 0.0916(10) Uani 1 1 d . . . C20 C 0.6974(3) -0.0535(3) 0.8910(4) 0.0924(15) Uani 1 1 d . . . H20A H 0.6684 -0.1207 0.9006 0.139 Uiso 1 1 calc R . . H20B H 0.7539 -0.0544 0.9346 0.139 Uiso 1 1 calc R . . H20C H 0.7038 -0.0433 0.8121 0.139 Uiso 1 1 calc R . . C4 C 0.2338(3) -0.0529(3) 0.6596(3) 0.0519(10) Uani 1 1 d . . . C5 C 0.2508(3) -0.0758(3) 0.7847(3) 0.0672(12) Uani 1 1 d . . . H5 H 0.2591 -0.0170 0.8334 0.081 Uiso 1 1 calc R . . C2 C 0.2332(3) -0.2537(3) 0.6397(3) 0.0677(12) Uani 1 1 d . . . H2 H 0.2284 -0.3141 0.5929 0.081 Uiso 1 1 calc R . . C7 C 0.1448(2) 0.0028(3) 0.6352(3) 0.0659(11) Uani 1 1 d . . . H7A H 0.1000 -0.0435 0.6597 0.079 Uiso 1 1 calc R . . H7B H 0.1454 0.0690 0.6787 0.079 Uiso 1 1 calc R . . C1 C 0.2428(3) -0.2682(3) 0.7631(3) 0.0686(12) Uani 1 1 d . . . C3 C 0.2310(3) -0.1569(3) 0.5928(3) 0.0638(11) Uani 1 1 d . . . H3 H 0.2276 -0.1525 0.5140 0.077 Uiso 1 1 calc R . . C8 C 0.1226(3) 0.0282(3) 0.5103(3) 0.0703(12) Uani 1 1 d . . . H8A H 0.1064 -0.0378 0.4695 0.084 Uiso 1 1 calc R . . H8B H 0.0726 0.0760 0.5009 0.084 Uiso 1 1 calc R . . C6 C 0.2550(3) -0.1719(3) 0.8311(3) 0.0695(12) Uani 1 1 d . . . H6 H 0.2661 -0.1780 0.9098 0.083 Uiso 1 1 calc R . . C17 C 0.4415(3) 0.1694(3) 0.8623(3) 0.0536(10) Uani 1 1 d . . . H17 H 0.4117 0.2275 0.8885 0.064 Uiso 1 1 calc R . . C19 C 0.3206(3) 0.1206(3) 0.7023(3) 0.0552(10) Uani 1 1 d . . . C15 C 0.5670(3) 0.0531(3) 0.8712(3) 0.0560(10) Uani 1 1 d . . . C16 C 0.5220(3) 0.1411(3) 0.9130(3) 0.0573(10) Uani 1 1 d . . . C11 C 0.3051(2) 0.0221(3) 0.6198(3) 0.0513(10) Uani 1 1 d . . . C12 C 0.3955(2) -0.0329(3) 0.6289(3) 0.0591(11) Uani 1 1 d . . . H12A H 0.3905 -0.1094 0.6429 0.071 Uiso 1 1 calc R . . H12B H 0.4224 -0.0227 0.5596 0.071 Uiso 1 1 calc R . . C13 C 0.4482(3) 0.0219(3) 0.7283(3) 0.0527(10) Uani 1 1 d . . . C18 C 0.4048(2) 0.1077(3) 0.7689(3) 0.0496(9) Uani 1 1 d . . . C14 C 0.5313(3) -0.0066(3) 0.7783(3) 0.0571(10) Uani 1 1 d . . . H14 H 0.5615 -0.0636 0.7504 0.069 Uiso 1 1 calc R . . C10 C 0.2796(3) 0.0703(3) 0.5006(3) 0.0542(10) Uani 1 1 d . . . C23 C 0.1052(3) 0.2137(3) 0.3461(3) 0.0638(11) Uani 1 1 d . . . C22 C 0.1708(3) 0.1251(3) 0.3464(3) 0.0664(12) Uani 1 1 d . . . H22A H 0.1473 0.0688 0.2949 0.080 Uiso 1 1 calc R . . H22B H 0.2230 0.1529 0.3183 0.080 Uiso 1 1 calc R . . C24 C 0.1114(3) 0.2898(4) 0.4288(4) 0.1005(17) Uani 1 1 d . . . H24 H 0.1559 0.2849 0.4888 0.121 Uiso 1 1 calc R . . C28 C 0.0410(3) 0.2246(4) 0.2564(4) 0.0932(15) Uani 1 1 d . . . H28 H 0.0369 0.1743 0.1978 0.112 Uiso 1 1 calc R . . C26 C -0.0126(5) 0.3817(6) 0.3343(7) 0.142(3) Uani 1 1 d . . . H26 H -0.0530 0.4375 0.3311 0.170 Uiso 1 1 calc R . . C25 C 0.0528(5) 0.3747(5) 0.4259(6) 0.143(3) Uani 1 1 d . . . H25 H 0.0571 0.4258 0.4837 0.172 Uiso 1 1 calc R . . C27 C -0.0174(4) 0.3084(6) 0.2511(6) 0.126(2) Uani 1 1 d . . . H27 H -0.0605 0.3141 0.1894 0.151 Uiso 1 1 calc R . . C21 C 0.5208(3) 0.2658(3) 1.0667(3) 0.0721(12) Uani 1 1 d . . . H21A H 0.4994 0.3235 1.0171 0.108 Uiso 1 1 calc R . . H21B H 0.5593 0.2943 1.1292 0.108 Uiso 1 1 calc R . . H21C H 0.4727 0.2302 1.0952 0.108 Uiso 1 1 calc R . . O4 O 0.64676(18) 0.0327(2) 0.9296(2) 0.0728(8) 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 N1 0.058(2) 0.0504(18) 0.0513(19) 0.0027(14) 0.0048(17) -0.0037(16) O5 0.0650(19) 0.084(2) 0.0763(19) -0.0314(16) 0.0028(16) 0.0109(15) O3 0.079(2) 0.0546(16) 0.0768(19) -0.0138(14) -0.0042(16) 0.0157(15) O2 0.076(2) 0.084(2) 0.0702(18) 0.0161(15) 0.0131(17) -0.0168(16) O1 0.139(3) 0.0624(19) 0.076(2) 0.0194(16) 0.0236(19) 0.0026(18) C20 0.072(3) 0.086(3) 0.120(4) -0.017(3) 0.013(3) 0.027(3) C4 0.074(3) 0.041(2) 0.041(2) 0.0023(17) 0.011(2) -0.002(2) C5 0.096(3) 0.061(3) 0.046(2) -0.006(2) 0.014(2) -0.009(2) C2 0.103(4) 0.052(2) 0.050(2) 0.0032(19) 0.018(2) -0.006(2) C7 0.077(3) 0.061(3) 0.063(3) 0.002(2) 0.023(2) -0.004(2) C1 0.088(3) 0.056(3) 0.063(3) 0.012(2) 0.017(2) 0.000(2) C3 0.090(3) 0.056(2) 0.047(2) -0.0021(19) 0.017(2) -0.010(2) C8 0.069(3) 0.069(3) 0.074(3) 0.006(2) 0.011(2) -0.016(2) C6 0.098(4) 0.066(3) 0.045(2) 0.004(2) 0.012(2) -0.006(2) C17 0.063(3) 0.043(2) 0.055(2) -0.0046(18) 0.011(2) 0.0044(19) C19 0.070(3) 0.039(2) 0.058(2) 0.0007(18) 0.016(2) 0.005(2) C15 0.052(3) 0.055(2) 0.061(2) 0.001(2) 0.012(2) 0.004(2) C16 0.066(3) 0.049(2) 0.058(2) -0.0092(19) 0.012(2) -0.002(2) C11 0.065(3) 0.042(2) 0.046(2) -0.0010(17) 0.006(2) 0.0010(19) C12 0.075(3) 0.045(2) 0.056(2) -0.0039(18) 0.006(2) 0.006(2) C13 0.068(3) 0.041(2) 0.052(2) 0.0030(18) 0.018(2) 0.001(2) C18 0.056(3) 0.038(2) 0.055(2) -0.0008(18) 0.007(2) 0.0050(19) C14 0.065(3) 0.047(2) 0.061(2) -0.0031(19) 0.015(2) 0.006(2) C10 0.065(3) 0.047(2) 0.052(2) -0.0042(18) 0.012(2) -0.008(2) C23 0.069(3) 0.060(3) 0.063(3) 0.008(2) 0.008(2) -0.003(2) C22 0.080(3) 0.067(3) 0.051(2) 0.001(2) 0.002(2) 0.002(2) C24 0.133(5) 0.068(3) 0.097(4) -0.007(3) -0.004(3) 0.031(3) C28 0.082(4) 0.111(4) 0.084(3) 0.025(3) -0.003(3) 0.005(3) C26 0.132(6) 0.135(6) 0.165(7) 0.074(5) 0.048(6) 0.065(5) C25 0.194(7) 0.105(5) 0.134(5) 0.002(4) 0.030(5) 0.078(5) C27 0.090(5) 0.156(7) 0.129(6) 0.068(5) 0.007(4) 0.019(5) C21 0.079(3) 0.068(3) 0.070(3) -0.024(2) 0.013(2) 0.005(2) O4 0.065(2) 0.0695(18) 0.084(2) -0.0115(15) 0.0070(16) 0.0143(15) _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 C10 1.346(4) . ? N1 C8 1.460(4) . ? N1 C22 1.474(4) . ? O5 C16 1.373(4) . ? O5 C21 1.418(4) . ? O3 C19 1.224(4) . ? O2 C10 1.230(4) . ? O1 C1 1.233(4) . ? C20 O4 1.432(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C4 C5 1.501(4) . ? C4 C3 1.512(5) . ? C4 C7 1.536(5) . ? C4 C11 1.557(5) . ? C5 C6 1.313(4) . ? C5 H5 0.9300 . ? C2 C3 1.323(4) . ? C2 C1 1.462(5) . ? C2 H2 0.9300 . ? C7 C8 1.511(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C1 C6 1.442(5) . ? C3 H3 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C6 H6 0.9300 . ? C17 C16 1.361(5) . ? C17 C18 1.407(4) . ? C17 H17 0.9300 . ? C19 C18 1.447(5) . ? C19 C11 1.566(5) . ? C15 O4 1.363(4) . ? C15 C14 1.386(5) . ? C15 C16 1.416(5) . ? C11 C10 1.540(5) . ? C11 C12 1.548(5) . ? C12 C13 1.511(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.377(4) . ? C13 C14 1.393(4) . ? C14 H14 0.9300 . ? C23 C24 1.356(5) . ? C23 C28 1.372(5) . ? C23 C22 1.496(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C24 C25 1.388(6) . ? C24 H24 0.9300 . ? C28 C27 1.374(7) . ? C28 H28 0.9300 . ? C26 C27 1.338(8) . ? C26 C25 1.394(8) . ? C26 H26 0.9300 . ? C25 H25 0.9300 . ? C27 H27 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 C10 N1 C8 125.5(3) . . ? C10 N1 C22 118.8(3) . . ? C8 N1 C22 114.8(3) . . ? C16 O5 C21 117.9(3) . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C5 C4 C3 110.2(3) . . ? C5 C4 C7 108.6(3) . . ? C3 C4 C7 108.5(3) . . ? C5 C4 C11 111.3(3) . . ? C3 C4 C11 109.3(3) . . ? C7 C4 C11 108.8(3) . . ? C6 C5 C4 125.4(3) . . ? C6 C5 H5 117.3 . . ? C4 C5 H5 117.3 . . ? C3 C2 C1 121.7(4) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C8 C7 C4 111.8(3) . . ? C8 C7 H7A 109.2 . . ? C4 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C4 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? O1 C1 C6 122.8(4) . . ? O1 C1 C2 120.7(4) . . ? C6 C1 C2 116.5(4) . . ? C2 C3 C4 124.1(3) . . ? C2 C3 H3 118.0 . . ? C4 C3 H3 118.0 . . ? N1 C8 C7 113.0(3) . . ? N1 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? N1 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C5 C6 C1 121.7(4) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? C16 C17 C18 117.9(3) . . ? C16 C17 H17 121.0 . . ? C18 C17 H17 121.0 . . ? O3 C19 C18 128.0(3) . . ? O3 C19 C11 123.6(3) . . ? C18 C19 C11 108.4(3) . . ? O4 C15 C14 123.6(3) . . ? O4 C15 C16 114.7(3) . . ? C14 C15 C16 121.7(4) . . ? C17 C16 O5 125.7(3) . . ? C17 C16 C15 120.4(3) . . ? O5 C16 C15 114.0(4) . . ? C10 C11 C12 111.5(3) . . ? C10 C11 C4 113.3(3) . . ? C12 C11 C4 112.3(3) . . ? C10 C11 C19 105.8(3) . . ? C12 C11 C19 103.3(3) . . ? C4 C11 C19 109.9(3) . . ? C13 C12 C11 104.7(3) . . ? C13 C12 H12A 110.8 . . ? C11 C12 H12A 110.8 . . ? C13 C12 H12B 110.8 . . ? C11 C12 H12B 110.8 . . ? H12A C12 H12B 108.9 . . ? C18 C13 C14 120.7(3) . . ? C18 C13 C12 112.4(3) . . ? C14 C13 C12 126.9(3) . . ? C13 C18 C17 121.9(3) . . ? C13 C18 C19 109.8(3) . . ? C17 C18 C19 128.4(3) . . ? C15 C14 C13 117.5(3) . . ? C15 C14 H14 121.3 . . ? C13 C14 H14 121.3 . . ? O2 C10 N1 122.0(3) . . ? O2 C10 C11 118.7(4) . . ? N1 C10 C11 119.1(4) . . ? C24 C23 C28 118.2(4) . . ? C24 C23 C22 121.4(4) . . ? C28 C23 C22 120.2(4) . . ? N1 C22 C23 112.7(3) . . ? N1 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? N1 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C23 C24 C25 121.5(5) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C23 C28 C27 121.4(5) . . ? C23 C28 H28 119.3 . . ? C27 C28 H28 119.3 . . ? C27 C26 C25 120.1(7) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C24 C25 C26 118.5(6) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? C26 C27 C28 120.2(7) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? O5 C21 H21A 109.5 . . ? O5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O5 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C15 O4 C20 118.2(3) . . ? 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 C3 C4 C5 C6 -5.7(6) . . . . ? C7 C4 C5 C6 113.0(4) . . . . ? C11 C4 C5 C6 -127.2(4) . . . . ? C5 C4 C7 C8 -179.8(3) . . . . ? C3 C4 C7 C8 -60.0(4) . . . . ? C11 C4 C7 C8 58.9(4) . . . . ? C3 C2 C1 O1 177.4(4) . . . . ? C3 C2 C1 C6 -3.5(6) . . . . ? C1 C2 C3 C4 -3.1(7) . . . . ? C5 C4 C3 C2 7.3(6) . . . . ? C7 C4 C3 C2 -111.5(4) . . . . ? C11 C4 C3 C2 129.9(4) . . . . ? C10 N1 C8 C7 23.4(5) . . . . ? C22 N1 C8 C7 -167.8(3) . . . . ? C4 C7 C8 N1 -46.9(4) . . . . ? C4 C5 C6 C1 -0.2(7) . . . . ? O1 C1 C6 C5 -175.7(4) . . . . ? C2 C1 C6 C5 5.1(6) . . . . ? C18 C17 C16 O5 -179.1(3) . . . . ? C18 C17 C16 C15 0.8(5) . . . . ? C21 O5 C16 C17 11.9(5) . . . . ? C21 O5 C16 C15 -167.9(3) . . . . ? O4 C15 C16 C17 -179.7(3) . . . . ? C14 C15 C16 C17 0.1(6) . . . . ? O4 C15 C16 O5 0.2(5) . . . . ? C14 C15 C16 O5 179.9(3) . . . . ? C5 C4 C11 C10 -165.9(3) . . . . ? C3 C4 C11 C10 72.1(4) . . . . ? C7 C4 C11 C10 -46.2(4) . . . . ? C5 C4 C11 C12 66.6(4) . . . . ? C3 C4 C11 C12 -55.3(4) . . . . ? C7 C4 C11 C12 -173.7(3) . . . . ? C5 C4 C11 C19 -47.8(4) . . . . ? C3 C4 C11 C19 -169.8(3) . . . . ? C7 C4 C11 C19 71.9(3) . . . . ? O3 C19 C11 C10 48.8(5) . . . . ? C18 C19 C11 C10 -128.8(3) . . . . ? O3 C19 C11 C12 166.0(3) . . . . ? C18 C19 C11 C12 -11.5(4) . . . . ? O3 C19 C11 C4 -73.9(4) . . . . ? C18 C19 C11 C4 108.5(3) . . . . ? C10 C11 C12 C13 123.8(3) . . . . ? C4 C11 C12 C13 -107.8(3) . . . . ? C19 C11 C12 C13 10.7(3) . . . . ? C11 C12 C13 C18 -6.8(4) . . . . ? C11 C12 C13 C14 172.8(3) . . . . ? C14 C13 C18 C17 -0.5(5) . . . . ? C12 C13 C18 C17 179.2(3) . . . . ? C14 C13 C18 C19 179.7(3) . . . . ? C12 C13 C18 C19 -0.6(4) . . . . ? C16 C17 C18 C13 -0.5(5) . . . . ? C16 C17 C18 C19 179.2(3) . . . . ? O3 C19 C18 C13 -169.6(4) . . . . ? C11 C19 C18 C13 7.8(4) . . . . ? O3 C19 C18 C17 10.7(6) . . . . ? C11 C19 C18 C17 -171.9(3) . . . . ? O4 C15 C14 C13 178.6(3) . . . . ? C16 C15 C14 C13 -1.1(5) . . . . ? C18 C13 C14 C15 1.3(5) . . . . ? C12 C13 C14 C15 -178.3(3) . . . . ? C8 N1 C10 O2 172.9(3) . . . . ? C22 N1 C10 O2 4.5(5) . . . . ? C8 N1 C10 C11 -11.9(5) . . . . ? C22 N1 C10 C11 179.8(3) . . . . ? C12 C11 C10 O2 -33.1(4) . . . . ? C4 C11 C10 O2 -160.9(3) . . . . ? C19 C11 C10 O2 78.6(4) . . . . ? C12 C11 C10 N1 151.5(3) . . . . ? C4 C11 C10 N1 23.7(4) . . . . ? C19 C11 C10 N1 -96.8(4) . . . . ? C10 N1 C22 C23 -128.5(4) . . . . ? C8 N1 C22 C23 61.9(4) . . . . ? C24 C23 C22 N1 42.8(5) . . . . ? C28 C23 C22 N1 -142.5(4) . . . . ? C28 C23 C24 C25 2.3(7) . . . . ? C22 C23 C24 C25 177.1(5) . . . . ? C24 C23 C28 C27 -1.8(7) . . . . ? C22 C23 C28 C27 -176.7(5) . . . . ? C23 C24 C25 C26 -1.1(9) . . . . ? C27 C26 C25 C24 -0.8(10) . . . . ? C25 C26 C27 C28 1.2(11) . . . . ? C23 C28 C27 C26 0.1(9) . . . . ? C14 C15 O4 C20 1.7(5) . . . . ? C16 C15 O4 C20 -178.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 28.44 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.199 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.044