Electronic Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author 'Jonathan Clayden' _publ_contact_author_address ; School of Chemistry The University of Manchester Oxford Rd Manchester M13 9PL UK ; _publ_contact_author_email J.P.CLAYDEN@MAN.AC.UK _publ_section_title ; Conformational preference in aromatic amides bearing chiral ortho substituents: its origin and application to relayed stereocontrol ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_contact_author_name 'Jonathan Clayden' loop_ _publ_author_name J.Clayden 'Mark S. Betson' 'Madeline Helliwell' 'Paul Johnson' 'Lai Wah Lai.' ; J.H.Pink ; 'Christopher C. Stimson' 'Neoclis Vassiliou' 'Neil Westlund' 'Samreen A. Yasin' 'Latifa H. Youssef' data_s2049m _database_code_depnum_ccdc_archive 'CCDC 286005' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; #------------------------------------------------------------------------------ _publ_section_exptl_refinement ; The structure was solved by direct methods. The non-H atoms were refined anisotropically, H atoms were included in calculated positions. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 N O2' _chemical_formula_weight 325.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3320(14) _cell_length_b 8.9703(18) _cell_length_c 14.588(3) _cell_angle_alpha 73.464(4) _cell_angle_beta 84.582(3) _cell_angle_gamma 77.268(3) _cell_volume 896.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1640 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 5134 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0692 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 26.38 _reflns_number_total 3546 _reflns_number_gt 2417 _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^)+(0.0372P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3546 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.892 _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 O1 O 1.03058(14) 0.51946(12) 0.24785(8) 0.0205(3) Uani 1 1 d . . . O2 O 1.03219(14) 0.83419(12) 0.17305(8) 0.0220(3) Uani 1 1 d . . . H2 H 1.0630 0.7349 0.1934 0.033 Uiso 1 1 calc R . . N1 N 0.75805(16) 0.43221(14) 0.28684(9) 0.0160(3) Uani 1 1 d . . . C1 C 0.80421(19) 0.61135(17) 0.12795(11) 0.0158(3) Uani 1 1 d . . . C2 C 0.7967(2) 0.77602(17) 0.08954(11) 0.0168(3) Uani 1 1 d . . . C3 C 0.7559(2) 0.84080(18) -0.00677(11) 0.0195(4) Uani 1 1 d . . . H3 H 0.7458 0.9518 -0.0340 0.023 Uiso 1 1 calc R . . C4 C 0.7295(2) 0.74859(19) -0.06417(12) 0.0219(4) Uani 1 1 d . . . H4 H 0.7036 0.7966 -0.1298 0.026 Uiso 1 1 calc R . . C5 C 0.7404(2) 0.58788(19) -0.02672(12) 0.0218(4) Uani 1 1 d . . . H5 H 0.7231 0.5241 -0.0660 0.026 Uiso 1 1 calc R . . C6 C 0.7771(2) 0.52096(18) 0.06918(11) 0.0199(4) Uani 1 1 d . . . H6 H 0.7840 0.4102 0.0956 0.024 Uiso 1 1 calc R . . C7 C 0.8689(2) 0.52100(17) 0.22743(11) 0.0171(3) Uani 1 1 d . . . C8 C 0.5540(2) 0.45700(18) 0.27437(11) 0.0175(3) Uani 1 1 d . . . H8 H 0.5199 0.5499 0.2174 0.021 Uiso 1 1 calc R . . C9 C 0.5018(2) 0.31412(18) 0.25451(12) 0.0229(4) Uani 1 1 d . . . H9A H 0.5691 0.2946 0.1964 0.034 Uiso 1 1 calc R . . H9B H 0.3667 0.3355 0.2457 0.034 Uiso 1 1 calc R . . H9C H 0.5359 0.2204 0.3087 0.034 Uiso 1 1 calc R . . C10 C 0.4408(2) 0.49707(18) 0.36065(11) 0.0204(4) Uani 1 1 d . . . H10A H 0.4570 0.4026 0.4155 0.031 Uiso 1 1 calc R . . H10B H 0.3081 0.5321 0.3455 0.031 Uiso 1 1 calc R . . H10C H 0.4846 0.5822 0.3763 0.031 Uiso 1 1 calc R . . C11 C 0.8345(2) 0.31291(18) 0.37506(11) 0.0199(4) Uani 1 1 d . . . H11 H 0.7312 0.2575 0.4061 0.024 Uiso 1 1 calc R . . C12 C 0.8889(2) 0.3870(2) 0.44773(12) 0.0259(4) Uani 1 1 d . . . H12A H 1.0021 0.4293 0.4244 0.039 Uiso 1 1 calc R . . H12B H 0.9130 0.3060 0.5090 0.039 Uiso 1 1 calc R . . H12C H 0.7867 0.4732 0.4566 0.039 Uiso 1 1 calc R . . C13 C 0.9929(2) 0.18614(18) 0.35168(12) 0.0250(4) Uani 1 1 d . . . H13A H 0.9538 0.1464 0.3022 0.038 Uiso 1 1 calc R . . H13B H 1.0232 0.0984 0.4095 0.038 Uiso 1 1 calc R . . H13C H 1.1035 0.2322 0.3283 0.038 Uiso 1 1 calc R . . C14 C 0.8378(2) 0.87816(18) 0.15061(11) 0.0187(4) Uani 1 1 d . . . C15 C 0.7095(2) 0.86637(17) 0.24023(11) 0.0179(3) Uani 1 1 d . . . C16 C 0.7769(2) 0.84911(18) 0.32957(11) 0.0224(4) Uani 1 1 d . . . H16 H 0.9079 0.8297 0.3376 0.027 Uiso 1 1 calc R . . C17 C 0.6539(2) 0.86010(18) 0.40701(12) 0.0270(4) Uani 1 1 d . . . H17 H 0.7016 0.8471 0.4677 0.032 Uiso 1 1 calc R . . C18 C 0.4631(2) 0.88973(18) 0.39649(12) 0.0255(4) Uani 1 1 d . . . H18 H 0.3795 0.9011 0.4491 0.031 Uiso 1 1 calc R . . C19 C 0.3942(2) 0.90273(18) 0.30878(12) 0.0245(4) Uani 1 1 d . . . H19 H 0.2631 0.9206 0.3014 0.029 Uiso 1 1 calc R . . C20 C 0.5165(2) 0.88967(17) 0.23196(12) 0.0206(4) Uani 1 1 d . . . H20 H 0.4683 0.8967 0.1724 0.025 Uiso 1 1 calc R . . C21 C 0.8098(2) 1.05490(18) 0.09792(12) 0.0222(4) Uani 1 1 d . . . H21A H 0.8459 1.1124 0.1389 0.033 Uiso 1 1 calc R . . H21B H 0.6780 1.0964 0.0822 0.033 Uiso 1 1 calc R . . H21C H 0.8877 1.0691 0.0389 0.033 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 O1 0.0160(6) 0.0237(6) 0.0219(6) -0.0037(5) -0.0035(5) -0.0059(4) O2 0.0166(6) 0.0214(6) 0.0291(7) -0.0074(6) -0.0027(5) -0.0047(4) N1 0.0153(7) 0.0180(7) 0.0151(7) -0.0030(6) -0.0028(6) -0.0050(5) C1 0.0122(7) 0.0206(8) 0.0152(8) -0.0054(7) 0.0007(6) -0.0045(6) C2 0.0133(7) 0.0186(8) 0.0180(9) -0.0048(7) 0.0006(7) -0.0030(6) C3 0.0193(8) 0.0192(8) 0.0192(9) -0.0027(7) -0.0018(7) -0.0052(7) C4 0.0237(9) 0.0264(9) 0.0153(9) -0.0038(7) -0.0021(7) -0.0061(7) C5 0.0241(9) 0.0249(9) 0.0198(9) -0.0096(8) -0.0025(7) -0.0067(7) C6 0.0209(8) 0.0191(8) 0.0204(9) -0.0052(7) 0.0014(7) -0.0066(7) C7 0.0183(8) 0.0166(8) 0.0176(9) -0.0074(7) -0.0003(7) -0.0025(6) C8 0.0136(7) 0.0192(8) 0.0197(9) -0.0051(7) -0.0025(7) -0.0031(6) C9 0.0199(8) 0.0272(9) 0.0252(10) -0.0108(8) -0.0004(7) -0.0079(7) C10 0.0178(8) 0.0225(8) 0.0209(9) -0.0060(7) 0.0000(7) -0.0042(7) C11 0.0183(8) 0.0213(8) 0.0173(9) 0.0007(7) -0.0024(7) -0.0052(7) C12 0.0261(9) 0.0336(10) 0.0166(9) -0.0055(8) -0.0034(7) -0.0040(7) C13 0.0253(9) 0.0220(9) 0.0250(10) -0.0024(8) -0.0047(8) -0.0026(7) C14 0.0161(8) 0.0202(8) 0.0208(9) -0.0066(7) -0.0014(7) -0.0043(6) C15 0.0216(8) 0.0123(8) 0.0202(9) -0.0052(7) -0.0003(7) -0.0038(6) C16 0.0262(9) 0.0203(9) 0.0218(9) -0.0062(8) -0.0039(7) -0.0052(7) C17 0.0400(11) 0.0237(9) 0.0189(9) -0.0071(8) -0.0026(8) -0.0074(8) C18 0.0344(10) 0.0199(9) 0.0204(10) -0.0059(8) 0.0085(8) -0.0050(7) C19 0.0233(9) 0.0178(8) 0.0298(10) -0.0051(8) 0.0037(8) -0.0029(7) C20 0.0227(9) 0.0194(8) 0.0196(9) -0.0045(7) -0.0022(7) -0.0045(7) C21 0.0222(8) 0.0229(9) 0.0229(9) -0.0077(8) 0.0020(7) -0.0067(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2456(17) . ? O2 C14 1.4358(17) . ? O2 H2 0.8400 . ? N1 C7 1.3437(19) . ? N1 C8 1.4843(18) . ? N1 C11 1.4845(19) . ? C1 C6 1.390(2) . ? C1 C2 1.413(2) . ? C1 C7 1.510(2) . ? C2 C3 1.393(2) . ? C2 C14 1.536(2) . ? C3 C4 1.385(2) . ? C3 H3 0.9500 . ? C4 C5 1.376(2) . ? C4 H4 0.9500 . ? C5 C6 1.383(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.524(2) . ? C8 C10 1.527(2) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C13 1.524(2) . ? C11 C12 1.524(2) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C21 1.529(2) . ? C14 C15 1.529(2) . ? C15 C16 1.393(2) . ? C15 C20 1.395(2) . ? C16 C17 1.390(2) . ? C16 H16 0.9500 . ? C17 C18 1.381(2) . ? C17 H17 0.9500 . ? C18 C19 1.385(2) . ? C18 H18 0.9500 . ? C19 C20 1.383(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C14 O2 H2 109.5 . . ? C7 N1 C8 123.19(12) . . ? C7 N1 C11 119.98(12) . . ? C8 N1 C11 116.56(12) . . ? C6 C1 C2 119.85(14) . . ? C6 C1 C7 116.42(13) . . ? C2 C1 C7 123.10(14) . . ? C3 C2 C1 117.11(14) . . ? C3 C2 C14 121.43(13) . . ? C1 C2 C14 121.44(14) . . ? C4 C3 C2 122.12(14) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C5 C4 C3 120.42(15) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 118.67(15) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 C1 121.80(14) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? O1 C7 N1 122.39(14) . . ? O1 C7 C1 118.39(14) . . ? N1 C7 C1 118.84(13) . . ? N1 C8 C9 111.80(12) . . ? N1 C8 C10 111.51(12) . . ? C9 C8 C10 110.51(13) . . ? N1 C8 H8 107.6 . . ? C9 C8 H8 107.6 . . ? C10 C8 H8 107.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C13 111.39(13) . . ? N1 C11 C12 113.17(12) . . ? C13 C11 C12 112.49(13) . . ? N1 C11 H11 106.4 . . ? C13 C11 H11 106.4 . . ? C12 C11 H11 106.4 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 C21 103.93(11) . . ? O2 C14 C15 112.28(12) . . ? C21 C14 C15 106.08(12) . . ? O2 C14 C2 109.48(12) . . ? C21 C14 C2 113.38(13) . . ? C15 C14 C2 111.47(12) . . ? C16 C15 C20 118.09(15) . . ? C16 C15 C14 121.85(14) . . ? C20 C15 C14 119.72(14) . . ? C17 C16 C15 120.45(15) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 120.60(16) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 119.57(16) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C20 C19 C18 119.87(15) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C15 121.34(15) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 119.3 . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C14 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 C6 C1 C2 C3 2.0(2) . . . . ? C7 C1 C2 C3 172.55(14) . . . . ? C6 C1 C2 C14 -176.21(13) . . . . ? C7 C1 C2 C14 -5.6(2) . . . . ? C1 C2 C3 C4 -2.1(2) . . . . ? C14 C2 C3 C4 176.10(14) . . . . ? C2 C3 C4 C5 0.9(2) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C4 C5 C6 C1 -0.4(2) . . . . ? C2 C1 C6 C5 -0.8(2) . . . . ? C7 C1 C6 C5 -171.95(14) . . . . ? C8 N1 C7 O1 166.28(13) . . . . ? C11 N1 C7 O1 -7.5(2) . . . . ? C8 N1 C7 C1 -20.9(2) . . . . ? C11 N1 C7 C1 165.25(12) . . . . ? C6 C1 C7 O1 111.14(16) . . . . ? C2 C1 C7 O1 -59.7(2) . . . . ? C6 C1 C7 N1 -61.95(19) . . . . ? C2 C1 C7 N1 127.19(15) . . . . ? C7 N1 C8 C9 116.18(15) . . . . ? C11 N1 C8 C9 -69.80(16) . . . . ? C7 N1 C8 C10 -119.54(15) . . . . ? C11 N1 C8 C10 54.48(16) . . . . ? C7 N1 C11 C13 -61.46(17) . . . . ? C8 N1 C11 C13 124.32(14) . . . . ? C7 N1 C11 C12 66.46(18) . . . . ? C8 N1 C11 C12 -107.76(14) . . . . ? C3 C2 C14 O2 -109.87(15) . . . . ? C1 C2 C14 O2 68.25(17) . . . . ? C3 C2 C14 C21 5.7(2) . . . . ? C1 C2 C14 C21 -176.20(13) . . . . ? C3 C2 C14 C15 125.30(15) . . . . ? C1 C2 C14 C15 -56.58(18) . . . . ? O2 C14 C15 C16 13.07(19) . . . . ? C21 C14 C15 C16 -99.81(16) . . . . ? C2 C14 C15 C16 136.32(14) . . . . ? O2 C14 C15 C20 -173.69(12) . . . . ? C21 C14 C15 C20 73.43(17) . . . . ? C2 C14 C15 C20 -50.44(18) . . . . ? C20 C15 C16 C17 -2.0(2) . . . . ? C14 C15 C16 C17 171.32(14) . . . . ? C15 C16 C17 C18 -0.6(2) . . . . ? C16 C17 C18 C19 2.4(2) . . . . ? C17 C18 C19 C20 -1.5(2) . . . . ? C18 C19 C20 C15 -1.2(2) . . . . ? C16 C15 C20 C19 2.9(2) . . . . ? C14 C15 C20 C19 -170.56(13) . . . . ? 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 O2 H2 O1 0.84 1.93 2.7240(15) 157.8 . _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.222 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.040 data_s803 _database_code_depnum_ccdc_archive 'CCDC 286006' #------------------------------------------------------------------------------ _audit_creation_date 19100-03-02 _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #------------------------------------------------------------------------------ _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Sheldrick, G.M. (1985). In: "Crystallographic Computing 3" (Eds G.M. Sheldrick, C. Kruger and R. Goddard) Oxford University Press, pp. 175-189. ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H45 N3 O3' _chemical_formula_weight 507.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.547(8) _cell_length_b 12.605(5) _cell_length_c 12.023(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.44(4) _cell_angle_gamma 90.00 _cell_volume 1588.3(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20.0 _cell_measurement_theta_max 28.1 _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.062 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.535 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.772 _exptl_special_details ; The scan width was (1.05+0.30tan\q)\% with an \w scan speed of 8\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.16 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -3 -2 1 -4 0 2 -1 3 _diffrn_reflns_number 3456 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 78.70 _reflns_number_total 3265 _reflns_number_gt 2142 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SHELXS86 (Sheldrick, 1985) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'teXsan (MSC, 1995)' _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 w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+0.1892P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(5) _refine_ls_number_reflns 3265 _refine_ls_number_parameters 344 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0981 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1645 _refine_ls_wR_factor_gt 0.1283 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5001(3) 0.9254(3) 0.1137(2) 0.0796(9) Uani 1 d . . . O2 O 0.8833(3) 0.8553(3) -0.0558(3) 0.0779(9) Uani 1 d . . . O3 O 0.8059(4) 1.1159(3) -0.2447(3) 0.0974(12) Uani 1 d . . . N1 N 0.5291(3) 0.7533(3) 0.0655(3) 0.0631(8) Uani 1 d . . . N2 N 0.8495(3) 1.0068(3) 0.0380(3) 0.0641(9) Uani 1 d . . . N3 N 0.8597(4) 0.9654(3) -0.3304(3) 0.0722(11) Uani 1 d . . . C1 C 0.5802(4) 0.8596(4) 0.0554(3) 0.0625(10) Uani 1 d . . . H1 H 0.6678 0.8625 0.0924 0.075 Uiso 1 calc R . . C2 C 0.4834(4) 0.7521(4) 0.1766(3) 0.0665(11) Uani 1 d . . . H2 H 0.4198 0.6958 0.1794 0.080 Uiso 1 calc R . . C3 C 0.4172(4) 0.8595(4) 0.1707(3) 0.0686(12) Uani 1 d . . . H3 H 0.3367 0.8519 0.1220 0.082 Uiso 1 calc R . . C4 C 0.6156(6) 0.6696(4) 0.0390(5) 0.0895(15) Uani 1 d . . . H4A H 0.6944 0.6757 0.0870 0.134 Uiso 1 calc R . . H4B H 0.6320 0.6762 -0.0376 0.134 Uiso 1 calc R . . H4C H 0.5776 0.6018 0.0502 0.134 Uiso 1 calc R . . C5 C 0.5858(5) 0.7410(5) 0.2759(4) 0.0848(15) Uani 1 d . . . H5A H 0.5465 0.7401 0.3441 0.127 Uiso 1 calc R . . H5B H 0.6438 0.7998 0.2769 0.127 Uiso 1 calc R . . H5C H 0.6318 0.6760 0.2691 0.127 Uiso 1 calc R . . C6 C 0.3881(4) 0.9117(5) 0.2771(3) 0.0728(13) Uani 1 d . . . C7 C 0.3103(5) 0.8603(6) 0.3466(4) 0.0880(16) Uani 1 d . . . H7 H 0.2793 0.7927 0.3282 0.106 Uiso 1 calc R . . C8 C 0.2788(6) 0.9097(7) 0.4432(5) 0.105(2) Uani 1 d . . . H8 H 0.2279 0.8744 0.4896 0.126 Uiso 1 calc R . . C9 C 0.3218(6) 1.0094(7) 0.4706(5) 0.108(2) Uani 1 d . . . H9 H 0.2992 1.0423 0.5347 0.130 Uiso 1 calc R . . C10 C 0.3981(7) 1.0606(7) 0.4036(5) 0.117(2) Uani 1 d . . . H10 H 0.4292 1.1279 0.4230 0.141 Uiso 1 calc R . . C11 C 0.4289(6) 1.0128(5) 0.3076(5) 0.0998(18) Uani 1 d . . . H11 H 0.4788 1.0498 0.2616 0.120 Uiso 1 calc R . . C12 C 0.5782(4) 0.8948(3) -0.0643(3) 0.0571(10) Uani 1 d . . . C13 C 0.6852(3) 0.9356(3) -0.1070(3) 0.0541(9) Uani 1 d . . . C14 C 0.6777(4) 0.9677(3) -0.2190(3) 0.0572(10) Uani 1 d . . . C15 C 0.5630(4) 0.9592(4) -0.2867(4) 0.0701(12) Uani 1 d . . . H15 H 0.5579 0.9805 -0.3611 0.084 Uiso 1 calc R . . C16 C 0.4560(4) 0.9193(5) -0.2446(4) 0.0782(13) Uani 1 d . . . H16 H 0.3791 0.9139 -0.2903 0.094 Uiso 1 calc R . . C17 C 0.4641(4) 0.8876(4) -0.1341(4) 0.0714(12) Uani 1 d . . . H17 H 0.3920 0.8610 -0.1059 0.086 Uiso 1 calc R . . C18 C 0.8160(4) 0.9317(4) -0.0394(3) 0.0598(10) Uani 1 d . . . C19 C 0.9737(4) 0.9990(5) 0.1085(4) 0.0844(15) Uani 1 d . . . H19 H 0.9791 1.0606 0.1584 0.101 Uiso 1 calc R . . C20 C 0.9788(6) 0.9011(7) 0.1831(5) 0.119(2) Uani 1 d . . . H20A H 0.9757 0.8384 0.1375 0.178 Uiso 1 calc R . . H20B H 0.9074 0.9016 0.2260 0.178 Uiso 1 calc R . . H20C H 1.0567 0.9016 0.2328 0.178 Uiso 1 calc R . . C21 C 1.0872(4) 1.0068(6) 0.0392(6) 0.115(2) Uani 1 d . . . H21A H 1.0791 1.0699 -0.0057 0.173 Uiso 1 calc R . . H21B H 1.0882 0.9458 -0.0085 0.173 Uiso 1 calc R . . H21C H 1.1652 1.0097 0.0886 0.173 Uiso 1 calc R . . C22 C 0.7729(4) 1.1028(4) 0.0534(4) 0.0693(11) Uani 1 d . . . H22 H 0.6936 1.0957 0.0030 0.083 Uiso 1 calc R . . C23 C 0.7352(5) 1.1093(5) 0.1723(5) 0.0938(16) Uani 1 d . . . H23A H 0.6684 1.1606 0.1747 0.141 Uiso 1 calc R . . H23B H 0.8079 1.1302 0.2228 0.141 Uiso 1 calc R . . H23C H 0.7057 1.0411 0.1940 0.141 Uiso 1 calc R . . C24 C 0.8378(5) 1.2025(4) 0.0193(5) 0.0823(14) Uani 1 d . . . H24A H 0.8490 1.1987 -0.0587 0.123 Uiso 1 calc R . . H24B H 0.9195 1.2092 0.0626 0.123 Uiso 1 calc R . . H24C H 0.7861 1.2629 0.0323 0.123 Uiso 1 calc R . . C25 C 0.7883(4) 1.0209(4) -0.2656(3) 0.0663(11) Uani 1 d . . . C26 C 0.8404(6) 0.8508(5) -0.3517(4) 0.0855(15) Uani 1 d . . . H26 H 0.7725 0.8274 -0.3081 0.103 Uiso 1 calc R . . C27 C 0.9591(8) 0.7870(7) -0.3117(6) 0.144(3) Uani 1 d . . . H27A H 1.0257 0.8038 -0.3571 0.216 Uiso 1 calc R . . H27B H 0.9399 0.7127 -0.3178 0.216 Uiso 1 calc R . . H27C H 0.9867 0.8044 -0.2351 0.216 Uiso 1 calc R . . C28 C 0.7952(7) 0.8295(6) -0.4742(5) 0.119(2) Uani 1 d . . . H28A H 0.7830 0.7546 -0.4855 0.178 Uiso 1 calc R . . H28B H 0.8581 0.8546 -0.5198 0.178 Uiso 1 calc R . . H28C H 0.7160 0.8658 -0.4947 0.178 Uiso 1 calc R . . C29 C 0.9633(6) 1.0200(7) -0.3828(5) 0.115(2) Uani 1 d . . . H29 H 1.0026 0.9659 -0.4264 0.138 Uiso 1 calc R . . C30 C 1.0682(7) 1.0594(11) -0.2947(8) 0.197(6) Uani 1 d . . . H30A H 1.0909 1.0039 -0.2415 0.295 Uiso 1 calc R . . H30B H 1.0381 1.1198 -0.2569 0.295 Uiso 1 calc R . . H30C H 1.1418 1.0791 -0.3304 0.295 Uiso 1 calc R . . C31 C 0.9073(11) 1.1030(8) -0.4667(8) 0.181(4) Uani 1 d . . . H31A H 0.9689 1.1204 -0.5169 0.271 Uiso 1 calc R . . H31B H 0.8861 1.1657 -0.4274 0.271 Uiso 1 calc R . . H31C H 0.8318 1.0752 -0.5087 0.271 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.109(2) 0.0675(19) 0.0694(18) 0.0027(16) 0.0411(17) -0.0006(19) O2 0.0694(19) 0.078(2) 0.087(2) -0.0058(17) 0.0109(16) 0.0214(17) O3 0.113(3) 0.078(2) 0.114(3) -0.014(2) 0.064(2) -0.024(2) N1 0.068(2) 0.058(2) 0.0657(19) 0.0014(17) 0.0175(16) -0.0052(17) N2 0.0462(17) 0.068(2) 0.077(2) -0.003(2) 0.0035(16) 0.0030(17) N3 0.075(2) 0.086(3) 0.0617(19) -0.0019(18) 0.0326(18) 0.005(2) C1 0.066(2) 0.065(3) 0.059(2) 0.002(2) 0.0183(19) -0.005(2) C2 0.065(2) 0.074(3) 0.062(2) 0.013(2) 0.0163(19) -0.013(2) C3 0.064(2) 0.087(3) 0.057(2) 0.008(2) 0.0137(19) -0.004(2) C4 0.103(4) 0.067(3) 0.104(4) 0.003(3) 0.035(3) 0.009(3) C5 0.083(3) 0.102(4) 0.071(3) 0.022(3) 0.016(2) 0.011(3) C6 0.059(2) 0.104(4) 0.056(2) 0.004(2) 0.0116(18) 0.008(3) C7 0.077(3) 0.121(5) 0.069(3) 0.003(3) 0.024(2) -0.001(3) C8 0.092(4) 0.156(7) 0.074(3) 0.005(4) 0.035(3) 0.005(4) C9 0.106(4) 0.145(6) 0.077(3) -0.018(4) 0.024(3) 0.026(5) C10 0.131(5) 0.133(6) 0.093(4) -0.033(4) 0.040(4) -0.004(4) C11 0.114(4) 0.106(5) 0.087(3) -0.013(3) 0.044(3) -0.008(4) C12 0.053(2) 0.061(2) 0.058(2) 0.0028(18) 0.0105(17) -0.0066(18) C13 0.0508(19) 0.055(2) 0.058(2) -0.0008(18) 0.0122(16) 0.0019(18) C14 0.055(2) 0.065(2) 0.055(2) -0.0025(18) 0.0185(18) 0.0005(18) C15 0.062(2) 0.090(3) 0.059(2) 0.006(2) 0.0104(19) 0.000(2) C16 0.060(2) 0.103(4) 0.070(3) 0.007(3) 0.002(2) -0.009(3) C17 0.057(2) 0.088(3) 0.071(3) 0.007(2) 0.0156(19) -0.017(2) C18 0.055(2) 0.068(3) 0.058(2) 0.004(2) 0.0139(18) 0.004(2) C19 0.056(2) 0.093(4) 0.099(4) -0.004(3) -0.015(2) 0.007(3) C20 0.108(4) 0.139(6) 0.101(4) 0.021(4) -0.024(3) 0.023(4) C21 0.049(3) 0.127(5) 0.166(6) 0.005(5) 0.000(3) -0.002(3) C22 0.054(2) 0.063(3) 0.089(3) -0.007(2) -0.001(2) 0.005(2) C23 0.094(4) 0.092(4) 0.099(4) -0.028(3) 0.030(3) -0.008(3) C24 0.076(3) 0.065(3) 0.103(4) -0.005(3) -0.002(3) -0.004(2) C25 0.070(3) 0.071(3) 0.062(2) 0.000(2) 0.022(2) -0.002(2) C26 0.110(4) 0.083(4) 0.070(3) 0.000(3) 0.036(3) 0.016(3) C27 0.190(8) 0.151(7) 0.095(4) 0.006(4) 0.034(5) 0.095(6) C28 0.146(6) 0.110(5) 0.101(4) -0.029(4) 0.020(4) 0.008(5) C29 0.107(4) 0.139(6) 0.112(4) -0.016(5) 0.069(4) -0.016(4) C30 0.092(5) 0.307(16) 0.204(9) -0.110(10) 0.073(6) -0.071(7) C31 0.254(11) 0.152(8) 0.161(8) 0.059(7) 0.129(8) -0.003(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 O1 C1 1.424(5) . ? O1 C3 1.434(5) . ? O2 C18 1.226(5) . ? O3 C25 1.233(6) . ? N1 C4 1.453(6) . ? N1 C1 1.454(6) . ? N1 C2 1.470(5) . ? N2 C18 1.346(5) . ? N2 C19 1.481(6) . ? N2 C22 1.478(6) . ? N3 C25 1.339(5) . ? N3 C26 1.477(7) . ? N3 C29 1.490(7) . ? C1 C12 1.504(5) . ? C1 H1 0.9800 . ? C2 C3 1.520(7) . ? C2 C5 1.523(6) . ? C2 H2 0.9800 . ? C3 C6 1.501(6) . ? C3 H3 0.9800 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C11 1.382(8) . ? C6 C7 1.395(6) . ? C7 C8 1.390(8) . ? C7 H7 0.9300 . ? C8 C9 1.364(11) . ? C8 H8 0.9300 . ? C9 C10 1.362(9) . ? C9 H9 0.9300 . ? C10 C11 1.373(8) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.390(5) . ? C12 C17 1.390(6) . ? C13 C14 1.400(5) . ? C13 C18 1.521(6) . ? C14 C15 1.384(6) . ? C14 C25 1.507(6) . ? C15 C16 1.382(6) . ? C15 H15 0.9300 . ? C16 C17 1.380(6) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C19 C20 1.523(9) . ? C19 C21 1.536(8) . ? C19 H19 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C24 1.509(7) . ? C22 C23 1.528(7) . ? C22 H22 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C26 C27 1.520(9) . ? C26 C28 1.520(8) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.527(10) . ? C29 C31 1.525(12) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 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 C1 O1 C3 108.9(3) . . ? C4 N1 C1 113.7(3) . . ? C4 N1 C2 118.0(4) . . ? C1 N1 C2 104.4(3) . . ? C18 N2 C19 119.7(4) . . ? C18 N2 C22 123.9(3) . . ? C19 N2 C22 116.3(4) . . ? C25 N3 C26 122.4(4) . . ? C25 N3 C29 119.5(5) . . ? C26 N3 C29 118.1(4) . . ? O1 C1 N1 104.5(3) . . ? O1 C1 C12 110.7(4) . . ? N1 C1 C12 112.7(3) . . ? O1 C1 H1 109.6 . . ? N1 C1 H1 109.6 . . ? C12 C1 H1 109.6 . . ? N1 C2 C3 98.3(3) . . ? N1 C2 C5 115.9(4) . . ? C3 C2 C5 113.6(4) . . ? N1 C2 H2 109.5 . . ? C3 C2 H2 109.5 . . ? C5 C2 H2 109.5 . . ? O1 C3 C6 110.3(4) . . ? O1 C3 C2 103.7(3) . . ? C6 C3 C2 119.1(4) . . ? O1 C3 H3 107.7 . . ? C6 C3 H3 107.7 . . ? C2 C3 H3 107.7 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 117.1(5) . . ? C11 C6 C3 122.9(4) . . ? C7 C6 C3 119.8(5) . . ? C8 C7 C6 120.3(6) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 120.7(6) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 119.7(6) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.0(7) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C6 122.1(6) . . ? C10 C11 H11 119.0 . . ? C6 C11 H11 119.0 . . ? C13 C12 C17 119.0(4) . . ? C13 C12 C1 122.5(3) . . ? C17 C12 C1 118.5(4) . . ? C12 C13 C14 120.1(3) . . ? C12 C13 C18 121.1(3) . . ? C14 C13 C18 118.2(3) . . ? C15 C14 C13 119.6(3) . . ? C15 C14 C25 118.6(4) . . ? C13 C14 C25 121.5(4) . . ? C16 C15 C14 120.6(4) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 119.5(4) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C12 121.2(4) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? O2 C18 N2 123.5(4) . . ? O2 C18 C13 116.5(4) . . ? N2 C18 C13 119.9(4) . . ? N2 C19 C20 111.3(5) . . ? N2 C19 C21 112.2(5) . . ? C20 C19 C21 113.1(5) . . ? N2 C19 H19 106.6 . . ? C20 C19 H19 106.6 . . ? C21 C19 H19 106.6 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N2 C22 C24 112.1(3) . . ? N2 C22 C23 111.4(4) . . ? C24 C22 C23 112.5(4) . . ? N2 C22 H22 106.8 . . ? C24 C22 H22 106.8 . . ? C23 C22 H22 106.8 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O3 C25 N3 122.9(4) . . ? O3 C25 C14 117.5(4) . . ? N3 C25 C14 119.5(4) . . ? N3 C26 C27 111.7(6) . . ? N3 C26 C28 111.3(5) . . ? C27 C26 C28 111.7(5) . . ? N3 C26 H26 107.3 . . ? C27 C26 H26 107.3 . . ? C28 C26 H26 107.3 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N3 C29 C30 111.5(5) . . ? N3 C29 C31 110.4(6) . . ? C30 C29 C31 115.6(9) . . ? N3 C29 H29 106.2 . . ? C30 C29 H29 106.2 . . ? C31 C29 H29 106.2 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 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 C3 O1 C1 N1 8.4(4) . . . . ? C3 O1 C1 C12 130.0(4) . . . . ? C4 N1 C1 O1 -164.1(4) . . . . ? C2 N1 C1 O1 -34.1(4) . . . . ? C4 N1 C1 C12 75.6(5) . . . . ? C2 N1 C1 C12 -154.4(3) . . . . ? C4 N1 C2 C3 171.6(4) . . . . ? C1 N1 C2 C3 44.2(4) . . . . ? C4 N1 C2 C5 50.3(6) . . . . ? C1 N1 C2 C5 -77.1(5) . . . . ? C1 O1 C3 C6 148.0(4) . . . . ? C1 O1 C3 C2 19.4(4) . . . . ? N1 C2 C3 O1 -38.4(4) . . . . ? C5 C2 C3 O1 84.6(4) . . . . ? N1 C2 C3 C6 -161.4(4) . . . . ? C5 C2 C3 C6 -38.4(5) . . . . ? O1 C3 C6 C11 4.9(6) . . . . ? C2 C3 C6 C11 124.6(5) . . . . ? O1 C3 C6 C7 -179.1(4) . . . . ? C2 C3 C6 C7 -59.4(6) . . . . ? C11 C6 C7 C8 -1.3(8) . . . . ? C3 C6 C7 C8 -177.6(5) . . . . ? C6 C7 C8 C9 0.9(9) . . . . ? C7 C8 C9 C10 -1.0(10) . . . . ? C8 C9 C10 C11 1.5(11) . . . . ? C9 C10 C11 C6 -2.0(11) . . . . ? C7 C6 C11 C10 1.8(9) . . . . ? C3 C6 C11 C10 178.0(6) . . . . ? O1 C1 C12 C13 114.5(4) . . . . ? N1 C1 C12 C13 -128.9(4) . . . . ? O1 C1 C12 C17 -64.5(5) . . . . ? N1 C1 C12 C17 52.1(5) . . . . ? C17 C12 C13 C14 -0.7(6) . . . . ? C1 C12 C13 C14 -179.7(4) . . . . ? C17 C12 C13 C18 -171.8(4) . . . . ? C1 C12 C13 C18 9.2(6) . . . . ? C12 C13 C14 C15 0.5(6) . . . . ? C18 C13 C14 C15 171.8(4) . . . . ? C12 C13 C14 C25 174.7(4) . . . . ? C18 C13 C14 C25 -14.0(6) . . . . ? C13 C14 C15 C16 -0.1(7) . . . . ? C25 C14 C15 C16 -174.4(5) . . . . ? C14 C15 C16 C17 -0.1(8) . . . . ? C15 C16 C17 C12 -0.2(8) . . . . ? C13 C12 C17 C16 0.6(7) . . . . ? C1 C12 C17 C16 179.6(5) . . . . ? C19 N2 C18 O2 -0.1(6) . . . . ? C22 N2 C18 O2 175.9(4) . . . . ? C19 N2 C18 C13 176.1(4) . . . . ? C22 N2 C18 C13 -7.9(6) . . . . ? C12 C13 C18 O2 93.5(5) . . . . ? C14 C13 C18 O2 -77.7(5) . . . . ? C12 C13 C18 N2 -83.0(5) . . . . ? C14 C13 C18 N2 105.8(4) . . . . ? C18 N2 C19 C20 -64.2(6) . . . . ? C22 N2 C19 C20 119.6(5) . . . . ? C18 N2 C19 C21 63.7(6) . . . . ? C22 N2 C19 C21 -112.5(5) . . . . ? C18 N2 C22 C24 -111.3(5) . . . . ? C19 N2 C22 C24 64.7(5) . . . . ? C18 N2 C22 C23 121.6(5) . . . . ? C19 N2 C22 C23 -62.3(5) . . . . ? C26 N3 C25 O3 177.9(5) . . . . ? C29 N3 C25 O3 -1.6(7) . . . . ? C26 N3 C25 C14 -4.7(7) . . . . ? C29 N3 C25 C14 175.7(5) . . . . ? C15 C14 C25 O3 95.6(5) . . . . ? C13 C14 C25 O3 -78.7(6) . . . . ? C15 C14 C25 N3 -81.9(5) . . . . ? C13 C14 C25 N3 103.8(5) . . . . ? C25 N3 C26 C27 -119.8(5) . . . . ? C29 N3 C26 C27 59.7(6) . . . . ? C25 N3 C26 C28 114.5(5) . . . . ? C29 N3 C26 C28 -66.0(7) . . . . ? C25 N3 C29 C30 65.0(8) . . . . ? C26 N3 C29 C30 -114.5(7) . . . . ? C25 N3 C29 C31 -64.9(7) . . . . ? C26 N3 C29 C31 115.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 78.70 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 0.142 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.034