# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Yoshitane Imai' _publ_contact_author_email Y-IMAI@APCH.KINDAI.AC.JP _publ_section_title ; Preparation of spontaneous resolution chiral fluorescent system using 2-anthracenecarboxylic acid ; loop_ _publ_author_name 'Yoshitane Imai' 'Michiya Fujiki' 'Takunori Harada' 'Kensaku Kamon' 'Reiko Kuroda' 'Yoshio Matsubara' ; K.Murata ; 'Tomohiro Sato' # Attachment 'IMAI85.CIF' data_imai85_1 _database_code_depnum_ccdc_archive 'CCDC 681595' #data_im7578a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H21 N O2' _chemical_formula_weight 343.41 _chemical_absolute_configuration rm 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.319(3) _cell_length_b 6.1500(17) _cell_length_c 15.347(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.088(5) _cell_angle_gamma 90.00 _cell_volume 879.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3257 _cell_measurement_theta_min 1.33 _cell_measurement_theta_max 27.87 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9561 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7730 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3934 _reflns_number_gt 3257 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.1658P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(15) _refine_ls_number_reflns 3934 _refine_ls_number_parameters 237 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1021(2) 0.7280(4) 0.76476(13) 0.0158(5) Uani 1 1 d . . . H1 H 0.0695 0.8694 0.7799 0.019 Uiso 1 1 calc R . . C2 C 0.2179(2) 0.6420(4) 0.80706(14) 0.0155(5) Uani 1 1 d . . . C3 C 0.2697(2) 0.4332(4) 0.78235(14) 0.0175(5) Uani 1 1 d . . . H3 H 0.3514 0.3746 0.8111 0.021 Uiso 1 1 calc R . . C4 C 0.2049(2) 0.3166(4) 0.71872(14) 0.0177(5) Uani 1 1 d . . . H4 H 0.2422 0.1784 0.7029 0.021 Uiso 1 1 calc R . . C5 C -0.1855(2) 0.2408(4) 0.50354(14) 0.0190(5) Uani 1 1 d . . . H5 H -0.1515 0.1010 0.4872 0.023 Uiso 1 1 calc R . . C6 C -0.3040(2) 0.3240(4) 0.46454(15) 0.0214(5) Uani 1 1 d . . . H6 H -0.3527 0.2412 0.4214 0.026 Uiso 1 1 calc R . . C7 C -0.3563(3) 0.5320(4) 0.48712(15) 0.0221(6) Uani 1 1 d . . . H7 H -0.4394 0.5877 0.4590 0.027 Uiso 1 1 calc R . . C8 C -0.2887(2) 0.6526(4) 0.54850(14) 0.0194(5) Uani 1 1 d . . . H8 H -0.3252 0.7921 0.5630 0.023 Uiso 1 1 calc R . . C9 C -0.0925(2) 0.6932(4) 0.65585(14) 0.0156(5) Uani 1 1 d . . . H9 H -0.1269 0.8335 0.6711 0.019 Uiso 1 1 calc R . . C10 C 0.0099(2) 0.2805(4) 0.61094(14) 0.0166(5) Uani 1 1 d . . . H10 H 0.0449 0.1408 0.5954 0.020 Uiso 1 1 calc R . . C11 C 0.0809(2) 0.3991(4) 0.67506(14) 0.0154(5) Uani 1 1 d . . . C12 C 0.0292(2) 0.6096(4) 0.69826(14) 0.0161(5) Uani 1 1 d . . . C13 C -0.1636(2) 0.5739(4) 0.59173(14) 0.0149(5) Uani 1 1 d . . . C14 C -0.1115(2) 0.3622(4) 0.56903(14) 0.0157(5) Uani 1 1 d . . . C15 C 0.2876(2) 0.7659(4) 0.88043(14) 0.0161(5) Uani 1 1 d . . . O16 O 0.25517(18) 0.9597(3) 0.89000(11) 0.0248(4) Uani 1 1 d . . . O17 O 0.37486(16) 0.6606(3) 0.92820(10) 0.0195(4) Uani 1 1 d . . . C21 C -0.7174(2) 0.4156(4) 0.14324(14) 0.0171(5) Uani 1 1 d . . . C22 C -0.6117(2) 0.3464(4) 0.20124(14) 0.0193(5) Uani 1 1 d . . . H22 H -0.5711 0.2056 0.1949 0.023 Uiso 1 1 calc R . . C23 C -0.5654(3) 0.4796(5) 0.26766(15) 0.0228(6) Uani 1 1 d . . . H23 H -0.4915 0.4317 0.3058 0.027 Uiso 1 1 calc R . . C24 C -0.6260(3) 0.6829(4) 0.27903(15) 0.0242(6) Uani 1 1 d . . . H24 H -0.5939 0.7752 0.3247 0.029 Uiso 1 1 calc R . . C25 C -0.7333(3) 0.7503(4) 0.22346(15) 0.0256(6) Uani 1 1 d . . . H25 H -0.7771 0.8883 0.2318 0.031 Uiso 1 1 calc R . . C26 C -0.7778(3) 0.6187(4) 0.15561(15) 0.0221(5) Uani 1 1 d . . . H26 H -0.8506 0.6683 0.1170 0.027 Uiso 1 1 calc R . . C27 C -0.7602(2) 0.2658(4) 0.06919(14) 0.0191(5) Uani 1 1 d . . . H27 H -0.7737 0.1164 0.0936 0.023 Uiso 1 1 calc R . . C28 C -0.8960(2) 0.3284(4) 0.02052(15) 0.0240(6) Uani 1 1 d . . . H28A H -0.8839 0.4728 -0.0054 0.036 Uiso 1 1 calc R . . H28B H -0.9770 0.3310 0.0612 0.036 Uiso 1 1 calc R . . H28C H -0.9148 0.2218 -0.0256 0.036 Uiso 1 1 calc R . . N29 N -0.64176(18) 0.2566(3) 0.00327(11) 0.0168(4) Uani 1 1 d . . . H29A H -0.6370 0.3855 -0.0257 0.025 Uiso 1 1 calc R . . H29B H -0.6596 0.1475 -0.0353 0.025 Uiso 1 1 calc R . . H29C H -0.5569 0.2311 0.0308 0.025 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 C1 0.0175(11) 0.0156(12) 0.0143(11) 0.0001(10) 0.0015(9) -0.0007(9) C2 0.0134(11) 0.0207(13) 0.0125(11) -0.0007(10) 0.0007(9) -0.0040(9) C3 0.0146(11) 0.0222(13) 0.0157(11) 0.0014(10) -0.0035(9) 0.0040(10) C4 0.0182(11) 0.0161(12) 0.0187(11) -0.0009(10) -0.0006(9) 0.0029(9) C5 0.0194(12) 0.0219(13) 0.0157(11) -0.0046(10) 0.0017(9) -0.0028(10) C6 0.0208(12) 0.0275(14) 0.0160(12) -0.0036(11) -0.0049(9) -0.0037(11) C7 0.0160(13) 0.0314(14) 0.0189(12) 0.0013(11) -0.0044(10) 0.0000(11) C8 0.0174(11) 0.0233(14) 0.0175(12) 0.0013(10) 0.0002(9) 0.0010(10) C9 0.0149(11) 0.0145(11) 0.0175(11) 0.0011(9) 0.0013(9) 0.0022(9) C10 0.0184(11) 0.0135(11) 0.0178(11) 0.0006(9) 0.0015(9) -0.0003(9) C11 0.0147(11) 0.0174(12) 0.0141(11) -0.0002(9) -0.0005(9) -0.0015(9) C12 0.0144(11) 0.0194(13) 0.0144(11) 0.0018(10) 0.0008(9) -0.0035(9) C13 0.0139(11) 0.0200(12) 0.0109(11) 0.0029(10) 0.0017(9) -0.0020(9) C14 0.0148(11) 0.0182(12) 0.0140(11) 0.0017(10) 0.0022(9) -0.0019(10) C15 0.0115(10) 0.0222(13) 0.0147(11) 0.0014(10) 0.0007(8) -0.0029(9) O16 0.0293(9) 0.0189(9) 0.0263(9) -0.0062(7) -0.0101(7) 0.0008(8) O17 0.0168(8) 0.0224(9) 0.0192(8) 0.0017(7) -0.0054(6) -0.0044(7) C21 0.0160(11) 0.0205(13) 0.0148(11) 0.0001(9) 0.0013(9) -0.0040(10) C22 0.0167(11) 0.0213(12) 0.0197(12) 0.0003(10) 0.0036(9) 0.0012(10) C23 0.0175(12) 0.0372(15) 0.0138(11) -0.0003(11) -0.0010(9) -0.0020(11) C24 0.0247(13) 0.0301(15) 0.0179(12) -0.0072(11) 0.0006(10) -0.0095(11) C25 0.0313(13) 0.0217(13) 0.0237(13) -0.0025(11) 0.0035(10) 0.0018(11) C26 0.0234(13) 0.0206(13) 0.0223(13) -0.0003(11) -0.0019(10) 0.0011(10) C27 0.0175(11) 0.0197(12) 0.0200(12) 0.0010(10) 0.0007(9) -0.0032(10) C28 0.0151(11) 0.0334(15) 0.0235(12) -0.0042(11) -0.0028(9) -0.0001(10) N29 0.0166(9) 0.0170(10) 0.0168(9) -0.0036(8) -0.0050(7) 0.0008(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 C1 C2 1.365(3) . ? C1 C12 1.425(3) . ? C2 C3 1.424(3) . ? C2 C15 1.506(3) . ? C3 C4 1.353(3) . ? C4 C11 1.428(3) . ? C5 C6 1.356(3) . ? C5 C14 1.429(3) . ? C6 C7 1.412(4) . ? C7 C8 1.354(3) . ? C8 C13 1.425(3) . ? C9 C13 1.394(3) . ? C9 C12 1.404(3) . ? C10 C11 1.392(3) . ? C10 C14 1.394(3) . ? C11 C12 1.427(3) . ? C13 C14 1.433(3) . ? C15 O16 1.239(3) . ? C15 O17 1.272(3) . ? C21 C26 1.383(3) . ? C21 C22 1.393(3) . ? C21 C27 1.516(3) . ? C22 C23 1.377(3) . ? C23 C24 1.383(4) . ? C24 C25 1.377(3) . ? C25 C26 1.382(3) . ? C27 N29 1.499(3) . ? C27 C28 1.518(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C12 121.2(2) . . ? C1 C2 C3 119.4(2) . . ? C1 C2 C15 119.9(2) . . ? C3 C2 C15 120.6(2) . . ? C4 C3 C2 121.2(2) . . ? C3 C4 C11 120.7(2) . . ? C6 C5 C14 120.4(2) . . ? C5 C6 C7 121.0(2) . . ? C8 C7 C6 120.5(2) . . ? C7 C8 C13 121.2(2) . . ? C13 C9 C12 121.1(2) . . ? C11 C10 C14 121.5(2) . . ? C10 C11 C12 119.41(19) . . ? C10 C11 C4 122.0(2) . . ? C12 C11 C4 118.6(2) . . ? C9 C12 C1 121.9(2) . . ? C9 C12 C11 119.3(2) . . ? C1 C12 C11 118.76(19) . . ? C9 C13 C8 122.5(2) . . ? C9 C13 C14 119.3(2) . . ? C8 C13 C14 118.2(2) . . ? C10 C14 C5 121.8(2) . . ? C10 C14 C13 119.4(2) . . ? C5 C14 C13 118.9(2) . . ? O16 C15 O17 125.3(2) . . ? O16 C15 C2 118.08(19) . . ? O17 C15 C2 116.6(2) . . ? C26 C21 C22 118.4(2) . . ? C26 C21 C27 123.0(2) . . ? C22 C21 C27 118.5(2) . . ? C23 C22 C21 120.8(2) . . ? C22 C23 C24 120.3(2) . . ? C25 C24 C23 119.4(2) . . ? C24 C25 C26 120.5(2) . . ? C25 C26 C21 120.7(2) . . ? N29 C27 C21 109.63(17) . . ? N29 C27 C28 106.95(18) . . ? C21 C27 C28 115.6(2) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.279 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.049 #==END data_imai85_2 _database_code_depnum_ccdc_archive 'CCDC 681596' #data_im8743a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 N O2' _chemical_formula_weight 349.46 _chemical_absolute_configuration rm 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.9057(9) _cell_length_b 6.1084(5) _cell_length_c 14.6448(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.4310(10) _cell_angle_gamma 90.00 _cell_volume 952.71(14) _cell_formula_units_Z 2 _cell_measurement_temperature 135(2) _cell_measurement_reflns_used 3527 _cell_measurement_theta_min 1.42 _cell_measurement_theta_max 27.85 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9590 _exptl_absorpt_correction_T_max 0.9924 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 135(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8407 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.85 _reflns_number_total 4179 _reflns_number_gt 3527 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(12) _refine_ls_number_reflns 4179 _refine_ls_number_parameters 237 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1123 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.60648(15) 0.4730(3) 0.23846(11) 0.0183(3) Uani 1 1 d . . . H1 H 0.5915 0.3307 0.2599 0.022 Uiso 1 1 calc R . . C2 C 0.71607(15) 0.5767(3) 0.27635(11) 0.0190(3) Uani 1 1 d . . . C3 C 0.73931(16) 0.7905(3) 0.24444(11) 0.0209(4) Uani 1 1 d . . . H3 H 0.8150 0.8638 0.2722 0.025 Uiso 1 1 calc R . . C4 C 0.65520(15) 0.8912(3) 0.17514(11) 0.0200(4) Uani 1 1 d . . . H4 H 0.6739 1.0317 0.1538 0.024 Uiso 1 1 calc R . . C5 C 0.23886(16) 0.8911(3) -0.04199(12) 0.0251(4) Uani 1 1 d . . . H5 H 0.2551 1.0302 -0.0659 0.030 Uiso 1 1 calc R . . C6 C 0.12629(17) 0.7929(3) -0.07431(13) 0.0299(4) Uani 1 1 d . . . H6 H 0.0646 0.8640 -0.1205 0.036 Uiso 1 1 calc R . . C7 C 0.09992(17) 0.5853(4) -0.03993(13) 0.0306(4) Uani 1 1 d . . . H7 H 0.0201 0.5197 -0.0623 0.037 Uiso 1 1 calc R . . C8 C 0.18819(16) 0.4789(3) 0.02511(12) 0.0256(4) Uani 1 1 d . . . H8 H 0.1697 0.3386 0.0467 0.031 Uiso 1 1 calc R . . C9 C 0.39910(15) 0.4726(3) 0.12918(11) 0.0193(4) Uani 1 1 d . . . H9 H 0.3830 0.3305 0.1502 0.023 Uiso 1 1 calc R . . C10 C 0.44875(15) 0.8880(3) 0.06436(11) 0.0205(4) Uani 1 1 d . . . H10 H 0.4663 1.0275 0.0414 0.025 Uiso 1 1 calc R . . C11 C 0.33347(15) 0.7880(3) 0.02764(11) 0.0199(4) Uani 1 1 d . . . C12 C 0.30772(15) 0.5754(3) 0.06101(11) 0.0208(4) Uani 1 1 d . . . C13 C 0.51339(15) 0.5739(3) 0.16704(11) 0.0177(3) Uani 1 1 d . . . C14 C 0.53884(15) 0.7874(3) 0.13407(11) 0.0181(3) Uani 1 1 d . . . C15 C 0.81197(15) 0.4659(3) 0.35235(11) 0.0213(4) Uani 1 1 d . . . O16 O 0.79522(12) 0.2700(2) 0.36860(9) 0.0342(3) Uani 1 1 d . . . O17 O 0.90396(11) 0.5808(2) 0.39436(8) 0.0251(3) Uani 1 1 d . . . C21 C 0.22651(15) 0.2007(3) 0.40154(12) 0.0212(4) Uani 1 1 d . . . H21 H 0.2351 0.0800 0.4486 0.025 Uiso 1 1 calc R . . C22 C 0.10023(16) 0.1735(3) 0.33331(12) 0.0260(4) Uani 1 1 d . . . H22A H 0.0320 0.1813 0.3682 0.031 Uiso 1 1 calc R . . H22B H 0.0883 0.2954 0.2877 0.031 Uiso 1 1 calc R . . C23 C 0.09146(18) -0.0434(3) 0.28086(13) 0.0314(4) Uani 1 1 d . . . H23A H 0.0104 -0.0505 0.2350 0.038 Uiso 1 1 calc R . . H23B H 0.0937 -0.1654 0.3257 0.038 Uiso 1 1 calc R . . C24 C 0.19868(19) -0.0708(4) 0.22997(13) 0.0385(5) Uani 1 1 d . . . H24A H 0.1946 -0.2188 0.2020 0.046 Uiso 1 1 calc R . . H24B H 0.1892 0.0377 0.1787 0.046 Uiso 1 1 calc R . . C25 C 0.32553(18) -0.0395(4) 0.29617(14) 0.0351(5) Uani 1 1 d . . . H25A H 0.3404 -0.1615 0.3417 0.042 Uiso 1 1 calc R . . H25B H 0.3924 -0.0437 0.2600 0.042 Uiso 1 1 calc R . . C26 C 0.33261(16) 0.1765(3) 0.34861(13) 0.0281(4) Uani 1 1 d . . . H26A H 0.3280 0.2987 0.3036 0.034 Uiso 1 1 calc R . . H26B H 0.4144 0.1861 0.3936 0.034 Uiso 1 1 calc R . . C27 C 0.23814(15) 0.4181(3) 0.45406(12) 0.0240(4) Uani 1 1 d . . . H27 H 0.2335 0.5388 0.4073 0.029 Uiso 1 1 calc R . . C28 C 0.36123(17) 0.4422(4) 0.52616(14) 0.0410(5) Uani 1 1 d . . . H28A H 0.3727 0.3156 0.5683 0.061 Uiso 1 1 calc R . . H28B H 0.3588 0.5763 0.5624 0.061 Uiso 1 1 calc R . . H28C H 0.4312 0.4502 0.4941 0.061 Uiso 1 1 calc R . . N27 N 0.13239(12) 0.4477(3) 0.50327(9) 0.0203(3) Uani 1 1 d . . . H27A H 0.1478 0.5665 0.5415 0.031 Uiso 1 1 calc R . . H27B H 0.1256 0.3264 0.5379 0.031 Uiso 1 1 calc R . . H27C H 0.0595 0.4684 0.4603 0.031 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 C1 0.0203(9) 0.0170(8) 0.0178(8) 0.0012(7) 0.0046(6) 0.0013(7) C2 0.0200(9) 0.0196(8) 0.0174(8) 0.0006(7) 0.0038(7) 0.0037(7) C3 0.0187(9) 0.0228(9) 0.0206(8) -0.0033(7) 0.0031(7) -0.0031(7) C4 0.0224(8) 0.0183(9) 0.0201(8) 0.0000(7) 0.0063(7) -0.0008(7) C5 0.0254(9) 0.0290(10) 0.0211(9) 0.0022(8) 0.0058(7) 0.0068(8) C6 0.0221(10) 0.0408(12) 0.0245(9) 0.0029(9) 0.0002(8) 0.0105(8) C7 0.0189(9) 0.0438(12) 0.0280(9) -0.0035(9) 0.0029(8) -0.0017(9) C8 0.0223(9) 0.0311(10) 0.0235(9) -0.0003(8) 0.0053(7) -0.0037(8) C9 0.0227(9) 0.0174(8) 0.0186(8) -0.0001(7) 0.0061(7) -0.0005(7) C10 0.0247(9) 0.0187(9) 0.0193(8) 0.0014(7) 0.0074(7) 0.0028(7) C11 0.0183(8) 0.0249(9) 0.0172(8) -0.0008(7) 0.0051(7) 0.0038(7) C12 0.0204(9) 0.0242(9) 0.0186(8) -0.0025(7) 0.0062(7) 0.0020(7) C13 0.0184(8) 0.0180(8) 0.0173(8) -0.0007(7) 0.0053(7) 0.0021(7) C14 0.0177(8) 0.0199(9) 0.0174(8) -0.0013(7) 0.0052(7) 0.0006(7) C15 0.0193(9) 0.0235(10) 0.0204(8) 0.0002(8) 0.0024(7) 0.0030(7) O16 0.0318(8) 0.0260(7) 0.0384(8) 0.0123(6) -0.0069(6) -0.0014(6) O17 0.0195(6) 0.0274(7) 0.0257(6) -0.0027(6) -0.0017(5) 0.0019(5) C21 0.0208(8) 0.0223(9) 0.0214(9) 0.0032(7) 0.0063(7) 0.0020(7) C22 0.0215(9) 0.0315(10) 0.0254(9) -0.0028(8) 0.0063(7) 0.0012(8) C23 0.0296(10) 0.0348(11) 0.0309(10) -0.0095(9) 0.0092(8) -0.0050(9) C24 0.0370(11) 0.0473(13) 0.0341(11) -0.0131(10) 0.0141(9) -0.0031(10) C25 0.0314(11) 0.0409(12) 0.0376(11) -0.0023(10) 0.0172(9) 0.0064(10) C26 0.0199(9) 0.0379(11) 0.0276(10) 0.0023(9) 0.0072(7) 0.0015(8) C27 0.0184(9) 0.0271(10) 0.0271(9) -0.0013(8) 0.0066(7) -0.0021(7) C28 0.0193(9) 0.0611(15) 0.0415(11) -0.0162(11) 0.0043(8) -0.0039(10) N27 0.0188(7) 0.0190(7) 0.0213(7) -0.0018(6) 0.0002(5) -0.0017(6) _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 C1 C2 1.361(2) . ? C1 C13 1.431(2) . ? C2 C3 1.428(2) . ? C2 C15 1.513(2) . ? C3 C4 1.360(2) . ? C4 C14 1.430(2) . ? C5 C6 1.357(3) . ? C5 C11 1.431(2) . ? C6 C7 1.416(3) . ? C7 C8 1.365(2) . ? C8 C12 1.424(2) . ? C9 C13 1.395(2) . ? C9 C12 1.399(2) . ? C10 C11 1.397(2) . ? C10 C14 1.398(2) . ? C11 C12 1.436(2) . ? C13 C14 1.438(2) . ? C15 O16 1.241(2) . ? C15 O17 1.270(2) . ? C21 C22 1.526(2) . ? C21 C27 1.526(2) . ? C21 C26 1.532(2) . ? C22 C23 1.524(3) . ? C23 C24 1.525(3) . ? C24 C25 1.521(3) . ? C25 C26 1.520(3) . ? C27 N27 1.497(2) . ? C27 C28 1.526(2) . ? 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 C2 C1 C13 121.33(16) . . ? C1 C2 C3 119.64(16) . . ? C1 C2 C15 119.92(16) . . ? C3 C2 C15 120.44(15) . . ? C4 C3 C2 121.28(16) . . ? C3 C4 C14 120.54(16) . . ? C6 C5 C11 120.88(18) . . ? C5 C6 C7 120.64(18) . . ? C8 C7 C6 120.53(17) . . ? C7 C8 C12 120.82(18) . . ? C13 C9 C12 121.53(16) . . ? C11 C10 C14 121.44(16) . . ? C10 C11 C5 122.20(16) . . ? C10 C11 C12 119.34(15) . . ? C5 C11 C12 118.46(16) . . ? C9 C12 C8 122.17(16) . . ? C9 C12 C11 119.17(15) . . ? C8 C12 C11 118.64(16) . . ? C9 C13 C1 122.14(15) . . ? C9 C13 C14 119.29(15) . . ? C1 C13 C14 118.56(14) . . ? C10 C14 C4 122.18(16) . . ? C10 C14 C13 119.20(15) . . ? C4 C14 C13 118.61(15) . . ? O16 C15 O17 125.01(16) . . ? O16 C15 C2 117.74(16) . . ? O17 C15 C2 117.25(16) . . ? C22 C21 C27 112.97(14) . . ? C22 C21 C26 109.36(13) . . ? C27 C21 C26 110.44(14) . . ? C23 C22 C21 111.99(15) . . ? C22 C23 C24 111.70(16) . . ? C25 C24 C23 111.26(15) . . ? C26 C25 C24 111.79(17) . . ? C25 C26 C21 112.20(15) . . ? N27 C27 C28 108.03(13) . . ? N27 C27 C21 111.03(14) . . ? C28 C27 C21 113.46(16) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.255 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.042 #==END data_imai85_3 _database_code_depnum_ccdc_archive 'CCDC 681597' #data_im6257a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H27 N O2' _chemical_formula_weight 385.49 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 18.2494(14) _cell_length_b 6.5375(5) _cell_length_c 17.7953(13) _cell_angle_alpha 90.00 _cell_angle_beta 99.5320(10) _cell_angle_gamma 90.00 _cell_volume 2093.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3578 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.84 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9700 _exptl_absorpt_correction_T_max 0.9962 _exptl_absorpt_process_details 'Bruker SADABS' _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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12454 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.84 _reflns_number_total 4745 _reflns_number_gt 3578 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.6927P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4745 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.1486 _refine_ls_wR_factor_gt 0.1367 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.74286(11) 0.0774(3) 0.52847(11) 0.0148(4) Uani 1 1 d . . . H1 H 0.7538 -0.0408 0.5013 0.018 Uiso 1 1 calc R . . C2 C 0.79244(11) 0.2355(3) 0.53782(10) 0.0137(4) Uani 1 1 d . . . C3 C 0.77511(11) 0.4162(3) 0.57631(11) 0.0146(4) Uani 1 1 d . . . H3 H 0.8086 0.5284 0.5812 0.018 Uiso 1 1 calc R . . C4 C 0.71132(11) 0.4298(3) 0.60598(11) 0.0159(4) Uani 1 1 d . . . H4 H 0.7010 0.5514 0.6315 0.019 Uiso 1 1 calc R . . C5 C 0.48012(12) 0.1064(4) 0.66028(12) 0.0223(5) Uani 1 1 d . . . H5 H 0.4694 0.2224 0.6887 0.027 Uiso 1 1 calc R . . C6 C 0.43329(12) -0.0559(4) 0.65305(13) 0.0251(5) Uani 1 1 d . . . H6 H 0.3903 -0.0523 0.6766 0.030 Uiso 1 1 calc R . . C7 C 0.44765(12) -0.2315(4) 0.61064(13) 0.0245(5) Uani 1 1 d . . . H7 H 0.4142 -0.3439 0.6060 0.029 Uiso 1 1 calc R . . C8 C 0.50909(12) -0.2391(3) 0.57671(12) 0.0201(5) Uani 1 1 d . . . H8 H 0.5180 -0.3570 0.5484 0.024 Uiso 1 1 calc R . . C9 C 0.62477(11) -0.0775(3) 0.55026(11) 0.0162(4) Uani 1 1 d . . . H9 H 0.6345 -0.1944 0.5218 0.019 Uiso 1 1 calc R . . C10 C 0.59483(11) 0.2699(3) 0.63208(11) 0.0163(4) Uani 1 1 d . . . H10 H 0.5842 0.3883 0.6593 0.020 Uiso 1 1 calc R . . C11 C 0.54552(11) 0.1053(3) 0.62554(11) 0.0165(4) Uani 1 1 d . . . C12 C 0.56055(11) -0.0721(3) 0.58307(11) 0.0170(5) Uani 1 1 d . . . C13 C 0.67520(11) 0.0851(3) 0.55829(11) 0.0135(4) Uani 1 1 d . . . C14 C 0.65954(11) 0.2649(3) 0.59944(11) 0.0145(4) Uani 1 1 d . . . C15 C 0.86693(11) 0.2117(3) 0.51216(10) 0.0130(4) Uani 1 1 d . . . O16 O 0.87919(8) 0.0522(2) 0.47757(8) 0.0167(3) Uani 1 1 d . . . O17 O 0.91419(8) 0.3545(2) 0.52871(8) 0.0178(3) Uani 1 1 d . . . C21 C 0.82914(11) -0.0887(3) 0.76261(10) 0.0132(4) Uani 1 1 d . . . C22 C 0.85573(11) -0.2870(3) 0.75542(11) 0.0165(4) Uani 1 1 d . . . H22 H 0.8355 -0.3966 0.7804 0.020 Uiso 1 1 calc R . . C23 C 0.91089(11) -0.3275(3) 0.71272(11) 0.0181(5) Uani 1 1 d . . . H23 H 0.9274 -0.4642 0.7085 0.022 Uiso 1 1 calc R . . C24 C 0.94247(11) -0.1708(3) 0.67586(11) 0.0157(4) Uani 1 1 d . . . C25 C 0.91678(11) 0.0262(3) 0.68326(11) 0.0171(5) Uani 1 1 d . . . H25 H 0.9379 0.1359 0.6590 0.021 Uiso 1 1 calc R . . C26 C 0.86088(11) 0.0668(3) 0.72531(10) 0.0157(4) Uani 1 1 d . . . H26 H 0.8439 0.2034 0.7287 0.019 Uiso 1 1 calc R . . C27 C 0.76706(11) -0.0492(3) 0.80940(11) 0.0148(4) Uani 1 1 d . . . C28 C 0.78848(13) -0.1433(4) 0.88934(11) 0.0231(5) Uani 1 1 d . . . H28A H 0.8348 -0.0811 0.9151 0.035 Uiso 1 1 calc R . . H28B H 0.7955 -0.2911 0.8847 0.035 Uiso 1 1 calc R . . H28C H 0.7488 -0.1177 0.9191 0.035 Uiso 1 1 calc R . . C29 C 0.69531(12) -0.1497(4) 0.76901(12) 0.0218(5) Uani 1 1 d . . . H29A H 0.6548 -0.1202 0.7973 0.033 Uiso 1 1 calc R . . H29B H 0.7025 -0.2980 0.7668 0.033 Uiso 1 1 calc R . . H29C H 0.6828 -0.0952 0.7172 0.033 Uiso 1 1 calc R . . C30 C 0.75303(12) 0.1792(3) 0.81887(12) 0.0192(5) Uani 1 1 d . . . H30A H 0.7161 0.1979 0.8525 0.029 Uiso 1 1 calc R . . H30B H 0.7344 0.2397 0.7690 0.029 Uiso 1 1 calc R . . H30C H 0.7996 0.2465 0.8412 0.029 Uiso 1 1 calc R . . C31 C 1.00141(12) -0.2138(4) 0.62807(11) 0.0201(5) Uani 1 1 d . . . H31A H 1.0352 -0.0947 0.6303 0.024 Uiso 1 1 calc R . . H31B H 1.0311 -0.3334 0.6493 0.024 Uiso 1 1 calc R . . N32 N 0.96879(9) -0.2558(3) 0.54702(9) 0.0153(4) Uani 1 1 d . . . H32A H 0.9415 -0.3729 0.5443 0.023 Uiso 1 1 calc R . . H32B H 1.0060 -0.2705 0.5191 0.023 Uiso 1 1 calc R . . H32C H 0.9390 -0.1497 0.5282 0.023 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 C1 0.0176(11) 0.0139(10) 0.0125(9) 0.0003(8) 0.0017(8) 0.0034(8) C2 0.0156(10) 0.0148(10) 0.0098(9) 0.0028(8) -0.0002(8) 0.0028(8) C3 0.0152(10) 0.0141(10) 0.0144(10) 0.0018(8) 0.0017(8) -0.0001(8) C4 0.0188(11) 0.0141(10) 0.0141(10) -0.0029(8) 0.0009(8) 0.0039(9) C5 0.0187(11) 0.0247(12) 0.0238(11) -0.0007(9) 0.0045(9) 0.0039(9) C6 0.0147(11) 0.0325(14) 0.0296(12) 0.0024(10) 0.0081(9) 0.0008(10) C7 0.0178(11) 0.0239(13) 0.0314(13) 0.0033(10) 0.0028(10) -0.0061(9) C8 0.0190(11) 0.0190(12) 0.0217(11) 0.0025(9) 0.0017(9) 0.0011(9) C9 0.0190(11) 0.0147(10) 0.0147(10) -0.0008(8) 0.0024(8) 0.0019(9) C10 0.0168(10) 0.0178(11) 0.0146(10) -0.0018(8) 0.0029(8) 0.0045(9) C11 0.0132(10) 0.0198(11) 0.0161(10) 0.0018(8) 0.0011(8) 0.0028(8) C12 0.0139(10) 0.0194(11) 0.0163(10) 0.0040(8) -0.0013(8) 0.0016(9) C13 0.0130(10) 0.0152(10) 0.0119(9) 0.0017(8) 0.0009(8) 0.0014(8) C14 0.0141(10) 0.0155(11) 0.0129(9) 0.0001(8) -0.0005(8) 0.0026(8) C15 0.0149(10) 0.0162(11) 0.0080(9) 0.0036(7) 0.0021(8) 0.0021(8) O16 0.0175(8) 0.0144(8) 0.0193(7) -0.0027(6) 0.0057(6) 0.0029(6) O17 0.0160(7) 0.0149(8) 0.0235(8) -0.0024(6) 0.0069(6) -0.0028(6) C21 0.0122(10) 0.0150(10) 0.0116(9) -0.0017(8) -0.0006(8) 0.0003(8) C22 0.0157(10) 0.0155(11) 0.0185(10) 0.0024(8) 0.0036(8) -0.0036(8) C23 0.0163(11) 0.0165(11) 0.0207(10) -0.0027(8) 0.0004(9) 0.0030(9) C24 0.0113(10) 0.0220(11) 0.0129(9) -0.0013(8) -0.0005(8) -0.0022(8) C25 0.0184(11) 0.0191(11) 0.0137(10) 0.0021(8) 0.0020(8) -0.0036(9) C26 0.0195(11) 0.0158(11) 0.0110(9) 0.0001(8) 0.0006(8) 0.0026(9) C27 0.0167(10) 0.0152(11) 0.0130(9) 0.0008(8) 0.0040(8) 0.0013(8) C28 0.0333(13) 0.0234(12) 0.0143(10) 0.0030(9) 0.0084(9) 0.0043(10) C29 0.0159(11) 0.0271(13) 0.0236(11) -0.0022(9) 0.0071(9) -0.0025(9) C30 0.0213(11) 0.0198(12) 0.0183(10) 0.0006(9) 0.0087(9) 0.0036(9) C31 0.0146(10) 0.0278(13) 0.0180(10) -0.0013(9) 0.0030(8) 0.0003(9) N32 0.0127(8) 0.0154(9) 0.0188(9) -0.0025(7) 0.0053(7) 0.0003(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 C1 C2 1.365(3) . ? C1 C13 1.423(3) . ? C2 C3 1.427(3) . ? C2 C15 1.512(3) . ? C3 C4 1.359(3) . ? C4 C14 1.425(3) . ? C5 C6 1.355(3) . ? C5 C11 1.432(3) . ? C6 C7 1.422(3) . ? C7 C8 1.359(3) . ? C8 C12 1.432(3) . ? C9 C12 1.394(3) . ? C9 C13 1.398(3) . ? C10 C11 1.395(3) . ? C10 C14 1.400(3) . ? C11 C12 1.435(3) . ? C13 C14 1.439(3) . ? C15 O16 1.250(2) . ? C15 O17 1.272(2) . ? C21 C26 1.392(3) . ? C21 C22 1.398(3) . ? C21 C27 1.535(3) . ? C22 C23 1.383(3) . ? C23 C24 1.392(3) . ? C24 C25 1.385(3) . ? C24 C31 1.504(3) . ? C25 C26 1.387(3) . ? C27 C30 1.529(3) . ? C27 C29 1.533(3) . ? C27 C28 1.540(3) . ? C31 N32 1.492(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C13 121.76(19) . . ? C1 C2 C3 119.33(19) . . ? C1 C2 C15 119.77(18) . . ? C3 C2 C15 120.77(18) . . ? C4 C3 C2 120.85(19) . . ? C3 C4 C14 121.21(19) . . ? C6 C5 C11 120.8(2) . . ? C5 C6 C7 120.9(2) . . ? C8 C7 C6 120.2(2) . . ? C7 C8 C12 121.0(2) . . ? C12 C9 C13 121.54(19) . . ? C11 C10 C14 121.60(19) . . ? C10 C11 C5 122.1(2) . . ? C10 C11 C12 119.37(19) . . ? C5 C11 C12 118.50(19) . . ? C9 C12 C8 122.2(2) . . ? C9 C12 C11 119.23(19) . . ? C8 C12 C11 118.53(19) . . ? C9 C13 C1 122.17(19) . . ? C9 C13 C14 119.39(18) . . ? C1 C13 C14 118.43(18) . . ? C10 C14 C4 122.82(19) . . ? C10 C14 C13 118.84(19) . . ? C4 C14 C13 118.34(18) . . ? O16 C15 O17 123.81(19) . . ? O16 C15 C2 118.53(18) . . ? O17 C15 C2 117.64(18) . . ? C26 C21 C22 117.11(18) . . ? C26 C21 C27 122.59(18) . . ? C22 C21 C27 120.29(18) . . ? C23 C22 C21 121.53(19) . . ? C22 C23 C24 120.9(2) . . ? C25 C24 C23 117.83(19) . . ? C25 C24 C31 120.84(19) . . ? C23 C24 C31 121.3(2) . . ? C24 C25 C26 121.34(19) . . ? C25 C26 C21 121.3(2) . . ? C30 C27 C29 108.95(18) . . ? C30 C27 C21 112.10(17) . . ? C29 C27 C21 108.85(16) . . ? C30 C27 C28 108.06(17) . . ? C29 C27 C28 109.16(17) . . ? C21 C27 C28 109.67(17) . . ? N32 C31 C24 111.89(16) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 27.84 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.314 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.057 #==END