# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Masami Sakamoto' _publ_contact_author_address ; Applied Chemistry and Biotechnology Chiba University, Faculty of Engineering Yayoi-cho Inage-ku Chiba Chiba 263-8522 JAPAN ; _publ_contact_author_email SAKAMOTOM@FACULTY.CHIBA-U.JP _publ_section_title ; Diastereoselective Photocycloaddition using Memory Effect of Molecular Chirality Controlled by Crystallization ; loop_ _publ_author_name 'Masami Sakamoto' 'Tsutomu Fujita' 'Yasuhiro Hasegawa' 'Yoshio Kasashima' 'Shuichiro Kobaru' 'Takashi Mino' ; A.Unosawa ; # Attachment 'sakamoto_1a_rev.cif' data_saka43_p21 _database_code_depnum_ccdc_archive 'CCDC 630580' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S,aR)-1a ; _chemical_name_common (S,aR)-1a _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N O4' _chemical_formula_weight 313.34 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 11.0267(17) _cell_length_b 6.9804(11) _cell_length_c 11.2114(17) _cell_angle_alpha 90.00 _cell_angle_beta 116.392(2) _cell_angle_gamma 90.00 _cell_volume 773.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 2170 _cell_measurement_theta_min 3.48 _cell_measurement_theta_max 27.73 _exptl_crystal_description cubic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9539 _exptl_absorpt_correction_T_max 0.9812 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _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 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4315 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.25 _reflns_number_total 2791 _reflns_number_gt 2571 _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^)+(0.0467P)^2^+0.1385P] 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 -0.1(11) _refine_ls_number_reflns 2791 _refine_ls_number_parameters 210 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.003 _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 C1 C 0.21002(16) 0.6117(3) 0.61870(15) 0.0255(4) Uani 1 1 d . . . C2 C 0.14393(16) 0.5866(2) 0.69640(15) 0.0226(3) Uani 1 1 d . . . C3 C 0.00056(16) 0.6001(3) 0.63936(16) 0.0240(3) Uani 1 1 d . . . C4 C -0.07255(18) 0.5840(3) 0.71575(17) 0.0312(4) Uani 1 1 d . . . H4 H -0.0250 0.5634 0.8091 0.037 Uiso 1 1 calc R . . C5 C -0.20988(18) 0.5976(3) 0.65709(19) 0.0378(5) Uani 1 1 d . . . H5 H -0.2570 0.5869 0.7101 0.045 Uiso 1 1 calc R . . C6 C -0.28341(18) 0.6274(3) 0.51870(19) 0.0373(4) Uani 1 1 d . . . H6 H -0.3794 0.6362 0.4788 0.045 Uiso 1 1 calc R . . C7 C -0.21635(18) 0.6433(3) 0.44281(17) 0.0326(4) Uani 1 1 d . . . H7 H -0.2662 0.6639 0.3497 0.039 Uiso 1 1 calc R . . C8 C -0.07341(17) 0.6297(3) 0.49977(15) 0.0254(3) Uani 1 1 d . . . C9 C -0.00147(17) 0.6459(3) 0.42279(15) 0.0276(4) Uani 1 1 d . . . H9 H -0.0504 0.6622 0.3292 0.033 Uiso 1 1 calc R . . C10 C 0.13588(17) 0.6389(3) 0.47923(16) 0.0282(4) Uani 1 1 d . . . H10 H 0.1821 0.6521 0.4256 0.034 Uiso 1 1 calc R . . C11 C 0.42104(19) 0.6384(4) 0.6065(2) 0.0417(5) Uani 1 1 d . . . H11A H 0.4028 0.5349 0.5416 0.063 Uiso 1 1 calc R . . H11B H 0.5183 0.6433 0.6660 0.063 Uiso 1 1 calc R . . H11C H 0.3919 0.7608 0.5594 0.063 Uiso 1 1 calc R . . C12 C 0.22066(17) 0.5269(3) 0.83980(16) 0.0241(4) Uani 1 1 d . . . C13 C 0.36023(16) 0.6156(3) 1.07079(15) 0.0275(4) Uani 1 1 d . . . H13 H 0.4194 0.5015 1.0827 0.033 Uiso 1 1 calc R . . C14 C 0.44790(19) 0.7930(3) 1.12925(18) 0.0354(4) Uani 1 1 d . . . H14A H 0.4669 0.8120 1.2234 0.043 Uiso 1 1 calc R . . H14B H 0.5347 0.7828 1.1236 0.043 Uiso 1 1 calc R . . C15 C 0.3615(2) 0.9554(3) 1.04214(19) 0.0367(5) Uani 1 1 d . . . H15A H 0.4182 1.0671 1.0452 0.044 Uiso 1 1 calc R . . H15B H 0.2926 0.9964 1.0708 0.044 Uiso 1 1 calc R . . C16 C 0.2949(2) 0.8682(3) 0.90282(18) 0.0317(4) Uani 1 1 d . . . H16A H 0.2036 0.9226 0.8496 0.038 Uiso 1 1 calc R . . H16B H 0.3508 0.8894 0.8551 0.038 Uiso 1 1 calc R . . C17 C 0.26828(19) 0.5787(3) 1.13662(17) 0.0351(4) Uani 1 1 d . . . C18 C 0.0454(2) 0.5928(4) 1.1165(2) 0.0533(6) Uani 1 1 d . . . H18A H 0.0548 0.4608 1.1492 0.080 Uiso 1 1 calc R . . H18B H -0.0471 0.6132 1.0471 0.080 Uiso 1 1 calc R . . H18C H 0.0642 0.6819 1.1903 0.080 Uiso 1 1 calc R . . N1 N 0.28723(14) 0.6632(2) 0.92940(13) 0.0251(3) Uani 1 1 d . . . O1 O 0.34835(12) 0.6035(2) 0.68268(11) 0.0346(3) Uani 1 1 d . . . O2 O 0.21985(13) 0.3589(2) 0.87355(12) 0.0335(3) Uani 1 1 d . . . O3 O 0.30940(19) 0.5191(4) 1.24701(17) 0.0847(8) Uani 1 1 d . . . O4 O 0.14032(12) 0.6261(2) 1.06189(12) 0.0383(3) 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 C1 0.0220(8) 0.0263(9) 0.0249(7) 0.0035(7) 0.0075(6) 0.0032(7) C2 0.0215(8) 0.0212(8) 0.0212(7) 0.0004(7) 0.0059(6) 0.0003(7) C3 0.0230(8) 0.0213(8) 0.0248(7) -0.0017(7) 0.0079(6) 0.0008(7) C4 0.0286(9) 0.0354(11) 0.0290(8) -0.0017(8) 0.0123(7) 0.0011(8) C5 0.0293(9) 0.0453(12) 0.0433(10) -0.0005(10) 0.0202(8) 0.0017(9) C6 0.0215(8) 0.0397(12) 0.0435(10) 0.0006(10) 0.0078(8) 0.0031(9) C7 0.0258(8) 0.0299(10) 0.0310(8) 0.0006(9) 0.0026(7) 0.0012(8) C8 0.0254(8) 0.0193(8) 0.0252(7) -0.0016(7) 0.0056(6) 0.0002(7) C9 0.0319(9) 0.0247(9) 0.0195(7) 0.0016(7) 0.0053(7) 0.0012(8) C10 0.0328(9) 0.0288(9) 0.0241(7) 0.0025(8) 0.0135(7) 0.0017(8) C11 0.0300(9) 0.0561(14) 0.0439(10) 0.0153(11) 0.0208(8) 0.0070(10) C12 0.0189(8) 0.0280(9) 0.0243(8) 0.0004(7) 0.0086(7) 0.0008(7) C13 0.0239(8) 0.0318(10) 0.0212(7) 0.0016(8) 0.0051(6) 0.0003(8) C14 0.0319(10) 0.0400(11) 0.0261(9) -0.0038(8) 0.0055(8) -0.0076(9) C15 0.0415(11) 0.0297(11) 0.0333(10) -0.0034(8) 0.0116(9) -0.0071(9) C16 0.0355(10) 0.0271(9) 0.0281(8) 0.0027(8) 0.0102(8) -0.0041(8) C17 0.0358(10) 0.0385(12) 0.0277(8) 0.0077(8) 0.0112(8) -0.0018(9) C18 0.0446(12) 0.0797(19) 0.0451(11) -0.0018(13) 0.0285(10) -0.0047(13) N1 0.0253(7) 0.0260(8) 0.0192(6) 0.0016(6) 0.0055(6) -0.0001(6) O1 0.0229(6) 0.0508(9) 0.0300(6) 0.0084(7) 0.0115(5) 0.0035(6) O2 0.0390(8) 0.0267(7) 0.0270(6) 0.0027(6) 0.0078(6) -0.0025(6) O3 0.0533(11) 0.152(2) 0.0466(9) 0.0524(12) 0.0208(8) 0.0084(12) O4 0.0307(7) 0.0575(10) 0.0287(6) 0.0002(7) 0.0151(5) 0.0013(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 O1 1.368(2) . ? C1 C2 1.373(2) . ? C1 C10 1.419(2) . ? C2 C3 1.421(2) . ? C2 C12 1.505(2) . ? C3 C4 1.418(2) . ? C3 C8 1.422(2) . ? C4 C5 1.360(3) . ? C4 H4 0.9500 . ? C5 C6 1.411(3) . ? C5 H5 0.9500 . ? C6 C7 1.357(3) . ? C6 H6 0.9500 . ? C7 C8 1.416(2) . ? C7 H7 0.9500 . ? C8 C9 1.413(2) . ? C9 C10 1.358(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 O1 1.429(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O2 1.234(2) . ? C12 N1 1.340(2) . ? C13 N1 1.4617(19) . ? C13 C17 1.518(2) . ? C13 C14 1.528(3) . ? C13 H13 1.0000 . ? C14 C15 1.523(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.527(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N1 1.472(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O3 1.188(2) . ? C17 O4 1.323(2) . ? C18 O4 1.447(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 O1 C1 C2 116.40(13) . . ? O1 C1 C10 123.05(14) . . ? C2 C1 C10 120.53(14) . . ? C1 C2 C3 120.28(14) . . ? C1 C2 C12 120.55(14) . . ? C3 C2 C12 118.94(13) . . ? C4 C3 C2 122.72(15) . . ? C4 C3 C8 118.32(14) . . ? C2 C3 C8 118.96(13) . . ? C5 C4 C3 120.82(16) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.95(16) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C7 C6 C5 119.65(16) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 121.27(16) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 122.26(15) . . ? C9 C8 C3 118.74(14) . . ? C7 C8 C3 119.00(14) . . ? C10 C9 C8 121.68(15) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C1 119.69(14) . . ? C9 C10 H10 120.2 . . ? C1 C10 H10 120.2 . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 N1 121.39(15) . . ? O2 C12 C2 120.89(16) . . ? N1 C12 C2 117.71(15) . . ? N1 C13 C17 113.64(13) . . ? N1 C13 C14 102.68(15) . . ? C17 C13 C14 111.16(15) . . ? N1 C13 H13 109.7 . . ? C17 C13 H13 109.7 . . ? C14 C13 H13 109.7 . . ? C15 C14 C13 103.42(14) . . ? C15 C14 H14A 111.1 . . ? C13 C14 H14A 111.1 . . ? C15 C14 H14B 111.1 . . ? C13 C14 H14B 111.1 . . ? H14A C14 H14B 109.0 . . ? C14 C15 C16 103.78(16) . . ? C14 C15 H15A 111.0 . . ? C16 C15 H15A 111.0 . . ? C14 C15 H15B 111.0 . . ? C16 C15 H15B 111.0 . . ? H15A C15 H15B 109.0 . . ? N1 C16 C15 103.04(15) . . ? N1 C16 H16A 111.2 . . ? C15 C16 H16A 111.2 . . ? N1 C16 H16B 111.2 . . ? C15 C16 H16B 111.2 . . ? H16A C16 H16B 109.1 . . ? O3 C17 O4 123.56(18) . . ? O3 C17 C13 122.54(18) . . ? O4 C17 C13 113.85(14) . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C12 N1 C13 120.38(15) . . ? C12 N1 C16 126.85(14) . . ? C13 N1 C16 112.76(14) . . ? C1 O1 C11 118.07(13) . . ? C17 O4 C18 117.39(15) . . ? 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 O1 C1 C2 C3 177.56(16) . . . . ? C10 C1 C2 C3 -4.2(3) . . . . ? O1 C1 C2 C12 -8.0(3) . . . . ? C10 C1 C2 C12 170.28(18) . . . . ? C1 C2 C3 C4 -177.12(17) . . . . ? C12 C2 C3 C4 8.4(3) . . . . ? C1 C2 C3 C8 3.3(3) . . . . ? C12 C2 C3 C8 -171.18(16) . . . . ? C2 C3 C4 C5 -179.93(19) . . . . ? C8 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 0.3(3) . . . . ? C6 C7 C8 C9 -180.0(2) . . . . ? C6 C7 C8 C3 -0.4(3) . . . . ? C4 C3 C8 C9 180.00(17) . . . . ? C2 C3 C8 C9 -0.4(2) . . . . ? C4 C3 C8 C7 0.5(2) . . . . ? C2 C3 C8 C7 -179.97(18) . . . . ? C7 C8 C9 C10 177.8(2) . . . . ? C3 C8 C9 C10 -1.7(3) . . . . ? C8 C9 C10 C1 1.0(3) . . . . ? O1 C1 C10 C9 -179.82(18) . . . . ? C2 C1 C10 C9 2.0(3) . . . . ? C1 C2 C12 O2 -100.4(2) . . . . ? C3 C2 C12 O2 74.1(2) . . . . ? C1 C2 C12 N1 81.0(2) . . . . ? C3 C2 C12 N1 -104.52(18) . . . . ? N1 C13 C14 C15 32.39(18) . . . . ? C17 C13 C14 C15 -89.47(18) . . . . ? C13 C14 C15 C16 -38.19(19) . . . . ? C14 C15 C16 N1 28.52(19) . . . . ? N1 C13 C17 O3 172.0(2) . . . . ? C14 C13 C17 O3 -72.8(3) . . . . ? N1 C13 C17 O4 -10.6(3) . . . . ? C14 C13 C17 O4 104.7(2) . . . . ? O2 C12 N1 C13 -0.5(2) . . . . ? C2 C12 N1 C13 178.11(14) . . . . ? O2 C12 N1 C16 -179.21(17) . . . . ? C2 C12 N1 C16 -0.6(2) . . . . ? C17 C13 N1 C12 -73.8(2) . . . . ? C14 C13 N1 C12 166.04(14) . . . . ? C17 C13 N1 C16 105.06(18) . . . . ? C14 C13 N1 C16 -15.10(18) . . . . ? C15 C16 N1 C12 170.41(15) . . . . ? C15 C16 N1 C13 -8.36(19) . . . . ? C2 C1 O1 C11 -176.96(18) . . . . ? C10 C1 O1 C11 4.8(3) . . . . ? O3 C17 O4 C18 -3.5(4) . . . . ? C13 C17 O4 C18 179.12(18) . . . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.194 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.035 # Attachment 'sakamoto_1b.cif.cif' data_saka16b_p21 _database_code_depnum_ccdc_archive 'CCDC 630581' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S,aR)-1b ; _chemical_name_common (S,aR)-1b _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H21 N O4' _chemical_formula_weight 327.37 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 7.6654(5) _cell_length_b 12.7990(8) _cell_length_c 9.0881(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.4860(10) _cell_angle_gamma 90.00 _cell_volume 879.44(10) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used 2565 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 26.04 _exptl_crystal_description cubic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9579 _exptl_absorpt_correction_T_max 0.9661 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4957 _diffrn_reflns_av_R_equivalents 0.0109 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.35 _reflns_number_total 3564 _reflns_number_gt 3211 _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^)+(0.1000P)^2^+1.0000P] 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 -0.5(12) _refine_ls_number_reflns 3564 _refine_ls_number_parameters 219 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 0.496 _refine_ls_restrained_S_all 0.496 _refine_ls_shift/su_max 0.074 _refine_ls_shift/su_mean 0.002 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 0.6944(2) 0.95407(15) 0.4590(2) 0.0464(4) Uani 1 1 d . . . C2 C 0.6337(3) 0.85604(16) 0.4779(2) 0.0557(5) Uani 1 1 d . . . C3 C 0.5556(3) 0.7960(2) 0.3518(3) 0.0698(6) Uani 1 1 d . . . H3 H 0.5109 0.7297 0.3647 0.084 Uiso 1 1 calc R . . C4 C 0.5473(3) 0.8365(2) 0.2130(3) 0.0706(7) Uani 1 1 d . . . H4 H 0.4968 0.7966 0.1315 0.085 Uiso 1 1 calc R . . C5 C 0.6114(3) 0.9353(2) 0.1878(2) 0.0590(5) Uani 1 1 d . . . C6 C 0.6083(3) 0.9780(3) 0.0425(2) 0.0731(8) Uani 1 1 d . . . H6 H 0.5594 0.9389 -0.0404 0.088 Uiso 1 1 calc R . . C7 C 0.6742(4) 1.0733(3) 0.0221(3) 0.0785(8) Uani 1 1 d . . . H7 H 0.6688 1.0998 -0.0739 0.094 Uiso 1 1 calc R . . C8 C 0.7499(4) 1.1318(2) 0.1437(3) 0.0750(7) Uani 1 1 d . . . H8 H 0.7972 1.1971 0.1285 0.090 Uiso 1 1 calc R . . C9 C 0.7565(3) 1.0953(2) 0.2874(2) 0.0605(5) Uani 1 1 d . . . H9 H 0.8073 1.1364 0.3676 0.073 Uiso 1 1 calc R . . C10 C 0.6873(2) 0.99672(17) 0.3137(2) 0.0500(4) Uani 1 1 d . . . C11 C 0.7640(2) 1.01994(14) 0.5933(2) 0.0435(4) Uani 1 1 d . . . C12 C 1.0706(3) 0.9546(2) 0.5857(3) 0.0706(6) Uani 1 1 d . . . H12A H 1.1028 0.9852 0.4963 0.085 Uiso 1 1 calc R . . H12B H 1.0283 0.8840 0.5638 0.085 Uiso 1 1 calc R . . C13 C 1.2232(4) 0.9558(3) 0.7112(4) 0.0906(9) Uani 1 1 d . . . H13A H 1.2148 0.8982 0.7791 0.109 Uiso 1 1 calc R . . H13B H 1.3341 0.9501 0.6736 0.109 Uiso 1 1 calc R . . C14 C 1.2126(3) 1.0579(2) 0.7885(3) 0.0753(7) Uani 1 1 d . . . H14A H 1.2755 1.1117 0.7434 0.090 Uiso 1 1 calc R . . H14B H 1.2631 1.0522 0.8934 0.090 Uiso 1 1 calc R . . C15 C 1.0141(3) 1.08323(16) 0.7694(2) 0.0518(5) Uani 1 1 d . . . H15 H 0.9665 1.0631 0.8590 0.062 Uiso 1 1 calc R . . C16 C 0.9789(3) 1.19756(17) 0.7351(2) 0.0528(5) Uani 1 1 d . . . C17 C 0.9361(4) 1.3610(2) 0.8419(4) 0.0839(8) Uani 1 1 d . . . H17B H 0.8228 1.3743 0.7824 0.126 Uiso 1 1 calc R . . H17C H 1.0273 1.3902 0.7938 0.126 Uiso 1 1 calc R . . H17A H 0.9407 1.3924 0.9384 0.126 Uiso 1 1 calc R . . C18 C 0.6613(6) 0.7105(3) 0.6436(4) 0.1048(11) Uani 1 1 d . . . H18A H 0.7415 0.6794 0.5837 0.126 Uiso 1 1 calc R . . H18B H 0.5450 0.6802 0.6133 0.126 Uiso 1 1 calc R . . C19 C 0.7231(6) 0.6897(3) 0.8004(5) 0.1235(14) Uani 1 1 d . . . H19B H 0.6413 0.7189 0.8586 0.185 Uiso 1 1 calc R . . H19A H 0.8374 0.7209 0.8299 0.185 Uiso 1 1 calc R . . H19C H 0.7314 0.6156 0.8164 0.185 Uiso 1 1 calc R . . N1 N 0.9372(2) 1.01806(13) 0.64257(18) 0.0495(4) Uani 1 1 d . . . O1 O 0.6637(2) 1.07557(12) 0.65212(16) 0.0585(4) Uani 1 1 d . . . O2 O 0.6537(3) 0.82079(13) 0.6213(2) 0.0766(5) Uani 1 1 d . . . O3 O 0.9726(3) 1.23640(13) 0.61535(19) 0.0772(5) Uani 1 1 d . . . O4 O 0.9625(2) 1.24976(13) 0.85871(18) 0.0656(4) 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 C1 0.0418(9) 0.0463(10) 0.0500(10) -0.0056(8) 0.0040(7) -0.0017(8) C2 0.0517(11) 0.0502(12) 0.0633(12) -0.0025(9) 0.0038(9) -0.0013(9) C3 0.0541(12) 0.0527(13) 0.0992(19) -0.0175(12) 0.0024(12) -0.0094(10) C4 0.0539(12) 0.0814(18) 0.0686(14) -0.0247(13) -0.0130(10) 0.0053(12) C5 0.0427(10) 0.0720(14) 0.0584(12) -0.0150(10) -0.0035(8) 0.0114(10) C6 0.0591(13) 0.111(2) 0.0445(11) -0.0177(12) -0.0063(9) 0.0270(14) C7 0.0732(16) 0.114(2) 0.0478(12) 0.0102(14) 0.0096(11) 0.0243(17) C8 0.0740(15) 0.0919(18) 0.0607(14) 0.0203(13) 0.0155(12) 0.0047(14) C9 0.0615(12) 0.0697(14) 0.0500(10) 0.0049(10) 0.0079(9) -0.0023(11) C10 0.0404(9) 0.0619(12) 0.0459(10) -0.0056(8) 0.0021(7) 0.0070(9) C11 0.0500(9) 0.0393(9) 0.0410(8) 0.0051(7) 0.0068(7) 0.0009(8) C12 0.0537(12) 0.0791(16) 0.0778(15) -0.0247(13) 0.0069(11) 0.0041(12) C13 0.0597(14) 0.095(2) 0.110(2) -0.0325(18) -0.0072(14) 0.0188(15) C14 0.0586(13) 0.0753(16) 0.0826(16) -0.0121(13) -0.0159(12) 0.0014(12) C15 0.0596(11) 0.0511(11) 0.0419(9) -0.0021(8) -0.0001(8) -0.0030(9) C16 0.0572(11) 0.0474(10) 0.0518(11) -0.0039(8) 0.0032(9) -0.0086(9) C17 0.0865(19) 0.0533(15) 0.116(2) -0.0206(14) 0.0297(17) -0.0122(13) C18 0.144(3) 0.0674(18) 0.100(2) 0.0235(16) 0.011(2) -0.008(2) C19 0.139(3) 0.110(3) 0.120(3) 0.047(2) 0.016(3) 0.001(3) N1 0.0493(8) 0.0486(8) 0.0489(8) -0.0089(7) 0.0030(7) -0.0005(7) O1 0.0588(8) 0.0637(9) 0.0521(7) -0.0059(7) 0.0065(6) 0.0145(7) O2 0.0960(13) 0.0559(10) 0.0772(11) 0.0092(8) 0.0119(9) -0.0128(9) O3 0.1149(15) 0.0563(10) 0.0596(9) 0.0085(8) 0.0120(9) -0.0132(9) O4 0.0838(10) 0.0499(8) 0.0642(9) -0.0121(7) 0.0151(8) -0.0105(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 1.359(3) . ? C1 C10 1.422(3) . ? C1 C11 1.506(3) . ? C2 O2 1.363(3) . ? C2 C3 1.427(3) . ? C3 C4 1.356(4) . ? C3 H3 0.9300 . ? C4 C5 1.389(4) . ? C4 H4 0.9300 . ? C5 C6 1.426(4) . ? C5 C10 1.430(3) . ? C6 C7 1.344(5) . ? C6 H6 0.9300 . ? C7 C8 1.381(4) . ? C7 H7 0.9300 . ? C8 C9 1.380(3) . ? C8 H8 0.9300 . ? C9 C10 1.405(3) . ? C9 H9 0.9300 . ? C11 O1 1.233(2) . ? C11 N1 1.329(2) . ? C12 N1 1.465(3) . ? C12 C13 1.493(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.492(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.538(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N1 1.465(2) . ? C15 C16 1.511(3) . ? C15 H15 0.9800 . ? C16 O3 1.191(3) . ? C16 O4 1.330(3) . ? C17 O4 1.442(3) . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17A 0.9600 . ? C18 O2 1.426(4) . ? C18 C19 1.450(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19B 0.9600 . ? C19 H19A 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 C2 C1 C10 120.67(18) . . ? C2 C1 C11 119.83(17) . . ? C10 C1 C11 119.46(17) . . ? C1 C2 O2 116.06(19) . . ? C1 C2 C3 120.2(2) . . ? O2 C2 C3 123.8(2) . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 122.5(2) . . ? C3 C4 H4 118.7 . . ? C5 C4 H4 118.8 . . ? C4 C5 C6 123.3(2) . . ? C4 C5 C10 118.5(2) . . ? C6 C5 C10 118.2(2) . . ? C7 C6 C5 121.8(2) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 121.3(3) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 120.6(2) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C1 123.03(19) . . ? C9 C10 C5 118.3(2) . . ? C1 C10 C5 118.69(19) . . ? O1 C11 N1 121.60(17) . . ? O1 C11 C1 120.75(17) . . ? N1 C11 C1 117.62(16) . . ? N1 C12 C13 103.27(19) . . ? N1 C12 H12A 111.1 . . ? C13 C12 H12A 111.1 . . ? N1 C12 H12B 111.1 . . ? C13 C12 H12B 111.1 . . ? H12A C12 H12B 109.1 . . ? C14 C13 C12 105.8(2) . . ? C14 C13 H13A 110.6 . . ? C12 C13 H13A 110.6 . . ? C14 C13 H13B 110.6 . . ? C12 C13 H13B 110.6 . . ? H13A C13 H13B 108.7 . . ? C13 C14 C15 105.1(2) . . ? C13 C14 H14A 110.7 . . ? C15 C14 H14A 110.7 . . ? C13 C14 H14B 110.7 . . ? C15 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? N1 C15 C16 110.77(16) . . ? N1 C15 C14 103.36(17) . . ? C16 C15 C14 111.55(19) . . ? N1 C15 H15 110.3 . . ? C16 C15 H15 110.3 . . ? C14 C15 H15 110.3 . . ? O3 C16 O4 124.5(2) . . ? O3 C16 C15 124.8(2) . . ? O4 C16 C15 110.56(17) . . ? O4 C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C17 H17A 109.5 . . ? H17B C17 H17A 109.5 . . ? H17C C17 H17A 109.5 . . ? O2 C18 C19 108.7(3) . . ? O2 C18 H18A 110.0 . . ? C19 C18 H18A 110.0 . . ? O2 C18 H18B 110.0 . . ? C19 C18 H18B 110.0 . . ? H18A C18 H18B 108.3 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19A 109.5 . . ? H19B C19 H19A 109.5 . . ? C18 C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? C11 N1 C12 127.41(16) . . ? C11 N1 C15 120.29(16) . . ? C12 N1 C15 112.29(16) . . ? C2 O2 C18 117.3(2) . . ? C16 O4 C17 115.9(2) . . ? 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 C10 C1 C2 O2 177.18(18) . . . . ? C11 C1 C2 O2 -5.0(3) . . . . ? C10 C1 C2 C3 -2.4(3) . . . . ? C11 C1 C2 C3 175.41(19) . . . . ? C1 C2 C3 C4 1.9(3) . . . . ? O2 C2 C3 C4 -177.7(2) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C3 C4 C5 C6 178.2(2) . . . . ? C3 C4 C5 C10 -0.6(3) . . . . ? C4 C5 C6 C7 -178.9(2) . . . . ? C10 C5 C6 C7 -0.1(3) . . . . ? C5 C6 C7 C8 1.0(4) . . . . ? C6 C7 C8 C9 -1.3(4) . . . . ? C7 C8 C9 C10 0.5(4) . . . . ? C8 C9 C10 C1 178.4(2) . . . . ? C8 C9 C10 C5 0.5(3) . . . . ? C2 C1 C10 C9 -176.6(2) . . . . ? C11 C1 C10 C9 5.6(3) . . . . ? C2 C1 C10 C5 1.4(3) . . . . ? C11 C1 C10 C5 -176.42(17) . . . . ? C4 C5 C10 C9 178.2(2) . . . . ? C6 C5 C10 C9 -0.7(3) . . . . ? C4 C5 C10 C1 0.1(3) . . . . ? C6 C5 C10 C1 -178.74(18) . . . . ? C2 C1 C11 O1 -87.9(2) . . . . ? C10 C1 C11 O1 89.9(2) . . . . ? C2 C1 C11 N1 94.0(2) . . . . ? C10 C1 C11 N1 -88.1(2) . . . . ? N1 C12 C13 C14 -30.2(3) . . . . ? C12 C13 C14 C15 31.5(3) . . . . ? C13 C14 C15 N1 -19.9(3) . . . . ? C13 C14 C15 C16 -138.9(2) . . . . ? N1 C15 C16 O3 -34.2(3) . . . . ? C14 C15 C16 O3 80.3(3) . . . . ? N1 C15 C16 O4 148.12(17) . . . . ? C14 C15 C16 O4 -97.3(2) . . . . ? O1 C11 N1 C12 178.7(2) . . . . ? C1 C11 N1 C12 -3.3(3) . . . . ? O1 C11 N1 C15 -0.2(3) . . . . ? C1 C11 N1 C15 177.81(17) . . . . ? C13 C12 N1 C11 -161.0(2) . . . . ? C13 C12 N1 C15 18.0(3) . . . . ? C16 C15 N1 C11 -60.3(2) . . . . ? C14 C15 N1 C11 -179.90(19) . . . . ? C16 C15 N1 C12 120.7(2) . . . . ? C14 C15 N1 C12 1.1(2) . . . . ? C1 C2 O2 C18 -155.0(3) . . . . ? C3 C2 O2 C18 24.6(4) . . . . ? C19 C18 O2 C2 166.9(3) . . . . ? O3 C16 O4 C17 -0.3(3) . . . . ? C15 C16 O4 C17 177.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 0.149 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.042 # Attachment 'sakamoto_2b.cif.cif' data_saka19b_p212121 _database_code_depnum_ccdc_archive 'CCDC 630582' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S)-2b ; _chemical_name_common (S)-2b _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H30 N2 O4' _chemical_formula_weight 530.60 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 10.1974(5) _cell_length_b 12.5011(6) _cell_length_c 21.8192(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2781.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223 _cell_measurement_reflns_used 3733 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 21.99 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details ; SADABS Sheldric 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 223 _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 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15835 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.14 _reflns_number_total 6390 _reflns_number_gt 4693 _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^)+(0.1000P)^2^+0.7126P] 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 0.0013(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(12) _refine_ls_number_reflns 6390 _refine_ls_number_parameters 364 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 0.768 _refine_ls_restrained_S_all 0.768 _refine_ls_shift/su_max 0.002 _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 0.6690(2) 0.76813(15) 0.24392(9) 0.0288(4) Uani 1 1 d . . . C2 C 0.55381(19) 0.84355(16) 0.23444(9) 0.0300(4) Uani 1 1 d . . . C3 C 0.5384(2) 0.92642(16) 0.27170(9) 0.0320(4) Uani 1 1 d . . . H3 H 0.4672 0.9735 0.2670 0.038 Uiso 1 1 calc R . . C4 C 0.6376(2) 0.94284(16) 0.32148(9) 0.0336(5) Uani 1 1 d . . . H4 H 0.6330 1.0183 0.3350 0.040 Uiso 1 1 calc R . . C5 C 0.7743(2) 0.92151(17) 0.29800(9) 0.0355(5) Uani 1 1 d . . . C6 C 0.8811(3) 0.9838(2) 0.31489(11) 0.0472(6) Uani 1 1 d . . . H6 H 0.8691 1.0441 0.3400 0.057 Uiso 1 1 calc R . . C7 C 1.0055(3) 0.9567(3) 0.29448(13) 0.0587(7) Uani 1 1 d . . . H7 H 1.0781 0.9987 0.3057 0.070 Uiso 1 1 calc R . . C8 C 1.0228(3) 0.8677(2) 0.25760(14) 0.0590(7) Uani 1 1 d . . . H8 H 1.1074 0.8489 0.2444 0.071 Uiso 1 1 calc R . . C9 C 0.9156(2) 0.8058(2) 0.23991(11) 0.0451(6) Uani 1 1 d . . . H9 H 0.9277 0.7454 0.2149 0.054 Uiso 1 1 calc R . . C10 C 0.7913(2) 0.83381(16) 0.25938(9) 0.0331(5) Uani 1 1 d . . . C11 C 0.69072(19) 0.69994(16) 0.18582(9) 0.0315(4) Uani 1 1 d . . . C12 C 0.7319(3) 0.86739(19) 0.12186(11) 0.0489(6) Uani 1 1 d . . . H12A H 0.8242 0.8894 0.1217 0.059 Uiso 1 1 calc R . . H12B H 0.6845 0.9092 0.1528 0.059 Uiso 1 1 calc R . . C13 C 0.6718(3) 0.8806(2) 0.06016(13) 0.0638(8) Uani 1 1 d . . . H13A H 0.7053 0.9449 0.0398 0.077 Uiso 1 1 calc R . . H13B H 0.5761 0.8856 0.0631 0.077 Uiso 1 1 calc R . . C14 C 0.7121(3) 0.7813(2) 0.02599(12) 0.0602(8) Uani 1 1 d . . . H14A H 0.7995 0.7899 0.0079 0.072 Uiso 1 1 calc R . . H14B H 0.6493 0.7645 -0.0066 0.072 Uiso 1 1 calc R . . C15 C 0.7127(2) 0.6926(2) 0.07562(10) 0.0419(5) Uani 1 1 d . . . H15 H 0.6301 0.6512 0.0736 0.050 Uiso 1 1 calc R . . C16 C 0.8285(3) 0.6190(2) 0.06699(11) 0.0434(6) Uani 1 1 d . . . C17 C 0.8975(4) 0.4625(3) 0.01544(19) 0.0832(12) Uani 1 1 d . . . H17A H 0.9528 0.4919 -0.0166 0.125 Uiso 1 1 calc R . . H17B H 0.8579 0.3965 0.0012 0.125 Uiso 1 1 calc R . . H17C H 0.9500 0.4483 0.0516 0.125 Uiso 1 1 calc R . . C18 C 0.3578(2) 0.8726(2) 0.17864(12) 0.0509(7) Uani 1 1 d . . . H18A H 0.3837 0.9434 0.1637 0.061 Uiso 1 1 calc R . . H18B H 0.3069 0.8815 0.2164 0.061 Uiso 1 1 calc R . . C19 C 0.2779(3) 0.8153(3) 0.13104(16) 0.0850(12) Uani 1 1 d . . . H19A H 0.3298 0.8062 0.0942 0.127 Uiso 1 1 calc R . . H19C H 0.2002 0.8569 0.1217 0.127 Uiso 1 1 calc R . . H19B H 0.2521 0.7457 0.1466 0.127 Uiso 1 1 calc R . . C20 C 0.6321(2) 0.69191(16) 0.30116(9) 0.0300(4) Uani 1 1 d . . . H20 H 0.6335 0.6169 0.2866 0.036 Uiso 1 1 calc R . . C21 C 0.6047(2) 0.86568(16) 0.38077(9) 0.0326(5) Uani 1 1 d . . . C22 C 0.5862(2) 0.9386(2) 0.43293(10) 0.0401(5) Uani 1 1 d . . . C23 C 0.7294(2) 0.70155(17) 0.35314(9) 0.0336(5) Uani 1 1 d . . . C24 C 0.8286(2) 0.62722(19) 0.36172(11) 0.0419(5) Uani 1 1 d . . . H24 H 0.8377 0.5697 0.3343 0.050 Uiso 1 1 calc R . . C25 C 0.9152(2) 0.6374(2) 0.41097(13) 0.0523(7) Uani 1 1 d . . . H25 H 0.9825 0.5869 0.4168 0.063 Uiso 1 1 calc R . . C26 C 0.9013(3) 0.7214(2) 0.45067(11) 0.0515(7) Uani 1 1 d . . . H26 H 0.9595 0.7280 0.4839 0.062 Uiso 1 1 calc R . . C27 C 0.8034(2) 0.7968(2) 0.44283(10) 0.0439(5) Uani 1 1 d . . . H27 H 0.7954 0.8542 0.4704 0.053 Uiso 1 1 calc R . . C28 C 0.7168(2) 0.78697(17) 0.39394(9) 0.0339(5) Uani 1 1 d . . . C29 C 0.4966(2) 0.71419(16) 0.32717(9) 0.0302(4) Uani 1 1 d . . . C30 C 0.3873(2) 0.65427(18) 0.31144(11) 0.0382(5) Uani 1 1 d . . . H30 H 0.3962 0.5967 0.2840 0.046 Uiso 1 1 calc R . . C31 C 0.2654(2) 0.6782(2) 0.33562(12) 0.0479(6) Uani 1 1 d . . . H31 H 0.1920 0.6369 0.3248 0.057 Uiso 1 1 calc R . . C32 C 0.2516(2) 0.7628(2) 0.37561(12) 0.0501(6) Uani 1 1 d . . . H32 H 0.1687 0.7788 0.3921 0.060 Uiso 1 1 calc R . . C33 C 0.3592(2) 0.82452(18) 0.39175(10) 0.0396(5) Uani 1 1 d . . . H33 H 0.3491 0.8826 0.4187 0.048 Uiso 1 1 calc R . . C34 C 0.4815(2) 0.80026(17) 0.36804(9) 0.0316(4) Uani 1 1 d . . . N1 N 0.7192(2) 0.75200(15) 0.13350(8) 0.0394(4) Uani 1 1 d . . . N2 N 0.5743(2) 0.99891(19) 0.47172(10) 0.0576(6) Uani 1 1 d . . . O1 O 0.68147(16) 0.60209(12) 0.18630(7) 0.0410(4) Uani 1 1 d . . . O2 O 0.47105(14) 0.80834(11) 0.18993(7) 0.0355(3) Uani 1 1 d . . . O3 O 0.9355(2) 0.63333(17) 0.08761(11) 0.0665(6) Uani 1 1 d . . . O4 O 0.7959(2) 0.53824(14) 0.03042(9) 0.0597(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0318(10) 0.0261(9) 0.0285(10) 0.0033(8) 0.0048(8) 0.0014(8) C2 0.0315(10) 0.0291(10) 0.0295(10) 0.0051(8) 0.0011(8) -0.0003(8) C3 0.0380(11) 0.0256(10) 0.0324(11) 0.0036(8) 0.0037(9) 0.0019(9) C4 0.0435(12) 0.0248(10) 0.0324(11) 0.0009(8) 0.0016(9) -0.0051(9) C5 0.0386(11) 0.0350(11) 0.0328(11) 0.0085(9) 0.0008(9) -0.0085(9) C6 0.0504(14) 0.0466(14) 0.0446(13) 0.0046(11) 0.0008(11) -0.0170(11) C7 0.0456(14) 0.0724(19) 0.0580(17) 0.0035(14) 0.0008(13) -0.0277(13) C8 0.0333(13) 0.080(2) 0.0633(17) 0.0030(15) 0.0090(12) -0.0110(13) C9 0.0367(12) 0.0529(14) 0.0458(13) 0.0020(11) 0.0085(10) -0.0023(11) C10 0.0328(10) 0.0337(11) 0.0328(10) 0.0064(8) 0.0033(9) -0.0040(9) C11 0.0309(10) 0.0303(10) 0.0333(10) 0.0005(8) 0.0036(8) 0.0024(9) C12 0.0651(16) 0.0391(13) 0.0426(13) 0.0107(10) 0.0165(12) 0.0019(11) C13 0.082(2) 0.0584(17) 0.0509(15) 0.0193(13) 0.0156(15) 0.0131(15) C14 0.0738(19) 0.0702(19) 0.0366(13) 0.0112(12) 0.0066(13) 0.0225(16) C15 0.0439(12) 0.0477(13) 0.0340(11) -0.0014(10) 0.0067(10) 0.0059(11) C16 0.0469(14) 0.0449(13) 0.0383(12) 0.0099(10) 0.0130(11) 0.0022(11) C17 0.093(3) 0.0493(18) 0.107(3) -0.0035(17) 0.054(2) 0.0122(16) C18 0.0414(13) 0.0624(17) 0.0490(14) -0.0139(12) -0.0105(11) 0.0143(12) C19 0.0633(19) 0.110(3) 0.081(2) -0.040(2) -0.0351(18) 0.0227(19) C20 0.0346(10) 0.0256(10) 0.0298(10) 0.0047(8) 0.0024(8) 0.0012(8) C21 0.0371(11) 0.0321(11) 0.0286(10) -0.0012(8) 0.0017(9) -0.0041(9) C22 0.0434(13) 0.0436(13) 0.0335(12) -0.0033(10) 0.0005(10) -0.0099(10) C23 0.0339(11) 0.0353(11) 0.0316(10) 0.0088(9) 0.0017(8) -0.0025(9) C24 0.0412(13) 0.0407(13) 0.0438(13) 0.0097(10) 0.0017(10) 0.0008(10) C25 0.0440(14) 0.0577(17) 0.0553(15) 0.0221(14) -0.0054(12) 0.0044(12) C26 0.0462(14) 0.0653(18) 0.0430(14) 0.0160(13) -0.0134(11) -0.0076(13) C27 0.0448(13) 0.0501(14) 0.0368(11) 0.0087(10) -0.0042(10) -0.0109(12) C28 0.0364(11) 0.0365(11) 0.0289(10) 0.0069(9) 0.0007(9) -0.0054(9) C29 0.0350(10) 0.0266(10) 0.0290(10) 0.0020(8) 0.0040(8) -0.0004(8) C30 0.0391(12) 0.0339(11) 0.0416(12) -0.0031(10) 0.0036(10) -0.0045(9) C31 0.0342(12) 0.0491(14) 0.0603(15) -0.0123(12) 0.0046(11) -0.0083(10) C32 0.0356(13) 0.0578(16) 0.0569(15) -0.0116(13) 0.0107(11) -0.0008(11) C33 0.0410(12) 0.0398(13) 0.0379(12) -0.0088(9) 0.0069(10) 0.0003(10) C34 0.0357(11) 0.0299(10) 0.0293(10) 0.0015(8) 0.0030(8) -0.0003(9) N1 0.0511(12) 0.0346(10) 0.0326(9) 0.0014(7) 0.0087(9) 0.0033(8) N2 0.0699(16) 0.0583(14) 0.0446(12) -0.0184(11) 0.0044(11) -0.0123(12) O1 0.0514(9) 0.0312(8) 0.0405(8) -0.0018(6) 0.0108(8) 0.0004(7) O2 0.0364(8) 0.0360(8) 0.0340(8) -0.0040(6) -0.0032(6) 0.0060(6) O3 0.0501(12) 0.0684(13) 0.0811(14) 0.0004(11) 0.0033(11) 0.0117(10) O4 0.0672(13) 0.0471(11) 0.0647(11) -0.0113(9) 0.0221(10) 0.0048(9) _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 1.520(3) . ? C1 C10 1.531(3) . ? C1 C11 1.544(3) . ? C1 C20 1.615(3) . ? C2 C3 1.326(3) . ? C2 O2 1.360(2) . ? C3 C4 1.499(3) . ? C3 H3 0.9400 . ? C4 C5 1.509(3) . ? C4 C21 1.648(3) . ? C4 H4 0.9900 . ? C5 C6 1.389(3) . ? C5 C10 1.394(3) . ? C6 C7 1.386(4) . ? C6 H6 0.9400 . ? C7 C8 1.384(4) . ? C7 H7 0.9400 . ? C8 C9 1.394(4) . ? C8 H8 0.9400 . ? C9 C10 1.381(3) . ? C9 H9 0.9400 . ? C11 O1 1.227(2) . ? C11 N1 1.346(3) . ? C12 N1 1.471(3) . ? C12 C13 1.488(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.506(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.549(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 N1 1.466(3) . ? C15 C16 1.510(3) . ? C15 H15 0.9900 . ? C16 O3 1.193(3) . ? C16 O4 1.329(3) . ? C17 O4 1.441(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 O2 1.428(3) . ? C18 C19 1.502(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C19 H19A 0.9700 . ? C19 H19C 0.9700 . ? C19 H19B 0.9700 . ? C20 C23 1.512(3) . ? C20 C29 1.519(3) . ? C20 H20 0.9900 . ? C21 C22 1.470(3) . ? C21 C34 1.524(3) . ? C21 C28 1.535(3) . ? C22 N2 1.140(3) . ? C23 C24 1.387(3) . ? C23 C28 1.396(3) . ? C24 C25 1.397(4) . ? C24 H24 0.9400 . ? C25 C26 1.369(4) . ? C25 H25 0.9400 . ? C26 C27 1.384(4) . ? C26 H26 0.9400 . ? C27 C28 1.390(3) . ? C27 H27 0.9400 . ? C29 C30 1.386(3) . ? C29 C34 1.406(3) . ? C30 C31 1.384(3) . ? C30 H30 0.9400 . ? C31 C32 1.378(3) . ? C31 H31 0.9400 . ? C32 C33 1.387(3) . ? C32 H32 0.9400 . ? C33 C34 1.384(3) . ? C33 H33 0.9400 . ? 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 C10 109.08(16) . . ? C2 C1 C11 109.98(16) . . ? C10 C1 C11 111.10(16) . . ? C2 C1 C20 106.92(15) . . ? C10 C1 C20 109.63(16) . . ? C11 C1 C20 110.04(15) . . ? C3 C2 O2 128.09(19) . . ? C3 C2 C1 119.52(18) . . ? O2 C2 C1 112.08(17) . . ? C2 C3 C4 118.10(19) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C3 C4 C5 110.70(17) . . ? C3 C4 C21 110.56(16) . . ? C5 C4 C21 110.56(17) . . ? C3 C4 H4 108.3 . . ? C5 C4 H4 108.3 . . ? C21 C4 H4 108.3 . . ? C6 C5 C10 120.3(2) . . ? C6 C5 C4 122.4(2) . . ? C10 C5 C4 117.36(18) . . ? C7 C6 C5 119.7(2) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.5(2) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 119.6(2) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C5 120.0(2) . . ? C9 C10 C1 122.95(19) . . ? C5 C10 C1 116.97(18) . . ? O1 C11 N1 120.40(19) . . ? O1 C11 C1 122.17(18) . . ? N1 C11 C1 117.42(17) . . ? N1 C12 C13 103.2(2) . . ? N1 C12 H12A 111.1 . . ? C13 C12 H12A 111.1 . . ? N1 C12 H12B 111.1 . . ? C13 C12 H12B 111.1 . . ? H12A C12 H12B 109.1 . . ? C12 C13 C14 104.1(2) . . ? C12 C13 H13A 110.9 . . ? C14 C13 H13A 110.9 . . ? C12 C13 H13B 110.9 . . ? C14 C13 H13B 110.9 . . ? H13A C13 H13B 109.0 . . ? C13 C14 C15 104.17(19) . . ? C13 C14 H14A 110.9 . . ? C15 C14 H14A 110.9 . . ? C13 C14 H14B 110.9 . . ? C15 C14 H14B 110.9 . . ? H14A C14 H14B 108.9 . . ? N1 C15 C16 112.4(2) . . ? N1 C15 C14 103.91(19) . . ? C16 C15 C14 110.59(19) . . ? N1 C15 H15 109.9 . . ? C16 C15 H15 109.9 . . ? C14 C15 H15 109.9 . . ? O3 C16 O4 124.7(2) . . ? O3 C16 C15 125.2(2) . . ? O4 C16 C15 110.0(2) . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O2 C18 C19 106.9(2) . . ? O2 C18 H18A 110.4 . . ? C19 C18 H18A 110.4 . . ? O2 C18 H18B 110.4 . . ? C19 C18 H18B 110.4 . . ? H18A C18 H18B 108.6 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? H19C C19 H19B 109.5 . . ? C23 C20 C29 107.58(16) . . ? C23 C20 C1 112.33(16) . . ? C29 C20 C1 113.11(16) . . ? C23 C20 H20 107.9 . . ? C29 C20 H20 107.9 . . ? C1 C20 H20 107.9 . . ? C22 C21 C34 111.57(18) . . ? C22 C21 C28 110.37(18) . . ? C34 C21 C28 107.68(16) . . ? C22 C21 C4 105.72(16) . . ? C34 C21 C4 109.80(16) . . ? C28 C21 C4 111.75(16) . . ? N2 C22 C21 176.7(3) . . ? C24 C23 C28 119.6(2) . . ? C24 C23 C20 121.8(2) . . ? C28 C23 C20 118.62(18) . . ? C23 C24 C25 120.3(2) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C26 C25 C24 119.4(2) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C25 C26 C27 121.3(2) . . ? C25 C26 H26 119.4 . . ? C27 C26 H26 119.4 . . ? C26 C27 C28 119.6(2) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C27 C28 C23 119.9(2) . . ? C27 C28 C21 124.1(2) . . ? C23 C28 C21 116.06(17) . . ? C30 C29 C34 118.87(19) . . ? C30 C29 C20 122.65(18) . . ? C34 C29 C20 118.47(18) . . ? C31 C30 C29 120.8(2) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C32 C31 C30 119.9(2) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C31 C32 C33 120.5(2) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C34 C33 C32 119.7(2) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C33 C34 C29 120.22(19) . . ? C33 C34 C21 123.85(19) . . ? C29 C34 C21 115.85(18) . . ? C11 N1 C15 118.44(18) . . ? C11 N1 C12 129.79(19) . . ? C15 N1 C12 110.59(18) . . ? C2 O2 C18 116.30(16) . . ? C16 O4 C17 117.1(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 C10 C1 C2 C3 -41.2(2) . . . . ? C11 C1 C2 C3 -163.33(18) . . . . ? C20 C1 C2 C3 77.2(2) . . . . ? C10 C1 C2 O2 144.58(16) . . . . ? C11 C1 C2 O2 22.5(2) . . . . ? C20 C1 C2 O2 -96.95(18) . . . . ? O2 C2 C3 C4 173.99(19) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 41.0(3) . . . . ? C2 C3 C4 C21 -81.8(2) . . . . ? C3 C4 C5 C6 140.5(2) . . . . ? C21 C4 C5 C6 -96.7(2) . . . . ? C3 C4 C5 C10 -41.3(2) . . . . ? C21 C4 C5 C10 81.6(2) . . . . ? C10 C5 C6 C7 -1.7(4) . . . . ? C4 C5 C6 C7 176.5(2) . . . . ? C5 C6 C7 C8 -0.2(4) . . . . ? C6 C7 C8 C9 1.0(4) . . . . ? C7 C8 C9 C10 0.0(4) . . . . ? C8 C9 C10 C5 -2.0(3) . . . . ? C8 C9 C10 C1 -177.8(2) . . . . ? C6 C5 C10 C9 2.8(3) . . . . ? C4 C5 C10 C9 -175.5(2) . . . . ? C6 C5 C10 C1 178.92(19) . . . . ? C4 C5 C10 C1 0.6(3) . . . . ? C2 C1 C10 C9 -144.5(2) . . . . ? C11 C1 C10 C9 -23.2(3) . . . . ? C20 C1 C10 C9 98.7(2) . . . . ? C2 C1 C10 C5 39.5(2) . . . . ? C11 C1 C10 C5 160.88(17) . . . . ? C20 C1 C10 C5 -77.3(2) . . . . ? C2 C1 C11 O1 -118.4(2) . . . . ? C10 C1 C11 O1 120.7(2) . . . . ? C20 C1 C11 O1 -0.9(3) . . . . ? C2 C1 C11 N1 60.9(2) . . . . ? C10 C1 C11 N1 -60.0(2) . . . . ? C20 C1 C11 N1 178.40(18) . . . . ? N1 C12 C13 C14 -36.9(3) . . . . ? C12 C13 C14 C15 34.7(3) . . . . ? C13 C14 C15 N1 -18.9(3) . . . . ? C13 C14 C15 C16 -139.7(2) . . . . ? N1 C15 C16 O3 -28.9(3) . . . . ? C14 C15 C16 O3 86.7(3) . . . . ? N1 C15 C16 O4 154.23(19) . . . . ? C14 C15 C16 O4 -90.2(2) . . . . ? C2 C1 C20 C23 -120.50(18) . . . . ? C10 C1 C20 C23 -2.4(2) . . . . ? C11 C1 C20 C23 120.09(18) . . . . ? C2 C1 C20 C29 1.5(2) . . . . ? C10 C1 C20 C29 119.64(18) . . . . ? C11 C1 C20 C29 -117.88(18) . . . . ? C3 C4 C21 C22 -120.98(19) . . . . ? C5 C4 C21 C22 116.07(19) . . . . ? C3 C4 C21 C34 -0.5(2) . . . . ? C5 C4 C21 C34 -123.45(19) . . . . ? C3 C4 C21 C28 118.91(19) . . . . ? C5 C4 C21 C28 -4.0(2) . . . . ? C34 C21 C22 N2 -132(5) . . . . ? C28 C21 C22 N2 108(5) . . . . ? C4 C21 C22 N2 -13(5) . . . . ? C29 C20 C23 C24 135.4(2) . . . . ? C1 C20 C23 C24 -99.5(2) . . . . ? C29 C20 C23 C28 -43.5(2) . . . . ? C1 C20 C23 C28 81.6(2) . . . . ? C28 C23 C24 C25 0.2(3) . . . . ? C20 C23 C24 C25 -178.7(2) . . . . ? C23 C24 C25 C26 0.0(3) . . . . ? C24 C25 C26 C27 -0.2(4) . . . . ? C25 C26 C27 C28 0.3(4) . . . . ? C26 C27 C28 C23 -0.1(3) . . . . ? C26 C27 C28 C21 -179.9(2) . . . . ? C24 C23 C28 C27 -0.1(3) . . . . ? C20 C23 C28 C27 178.81(19) . . . . ? C24 C23 C28 C21 179.68(19) . . . . ? C20 C23 C28 C21 -1.4(3) . . . . ? C22 C21 C28 C27 -11.2(3) . . . . ? C34 C21 C28 C27 -133.2(2) . . . . ? C4 C21 C28 C27 106.1(2) . . . . ? C22 C21 C28 C23 168.97(18) . . . . ? C34 C21 C28 C23 47.0(2) . . . . ? C4 C21 C28 C23 -73.7(2) . . . . ? C23 C20 C29 C30 -137.7(2) . . . . ? C1 C20 C29 C30 97.6(2) . . . . ? C23 C20 C29 C34 43.4(2) . . . . ? C1 C20 C29 C34 -81.3(2) . . . . ? C34 C29 C30 C31 -0.2(3) . . . . ? C20 C29 C30 C31 -179.1(2) . . . . ? C29 C30 C31 C32 0.3(4) . . . . ? C30 C31 C32 C33 0.2(4) . . . . ? C31 C32 C33 C34 -0.7(4) . . . . ? C32 C33 C34 C29 0.7(3) . . . . ? C32 C33 C34 C21 177.4(2) . . . . ? C30 C29 C34 C33 -0.3(3) . . . . ? C20 C29 C34 C33 178.7(2) . . . . ? C30 C29 C34 C21 -177.17(19) . . . . ? C20 C29 C34 C21 1.8(3) . . . . ? C22 C21 C34 C33 15.1(3) . . . . ? C28 C21 C34 C33 136.3(2) . . . . ? C4 C21 C34 C33 -101.8(2) . . . . ? C22 C21 C34 C29 -168.18(18) . . . . ? C28 C21 C34 C29 -46.9(2) . . . . ? C4 C21 C34 C29 74.9(2) . . . . ? O1 C11 N1 C15 12.1(3) . . . . ? C1 C11 N1 C15 -167.15(18) . . . . ? O1 C11 N1 C12 178.4(2) . . . . ? C1 C11 N1 C12 -0.9(4) . . . . ? C16 C15 N1 C11 -75.7(3) . . . . ? C14 C15 N1 C11 164.8(2) . . . . ? C16 C15 N1 C12 115.6(2) . . . . ? C14 C15 N1 C12 -4.0(3) . . . . ? C13 C12 N1 C11 -141.5(3) . . . . ? C13 C12 N1 C15 25.6(3) . . . . ? C3 C2 O2 C18 5.0(3) . . . . ? C1 C2 O2 C18 178.52(18) . . . . ? C19 C18 O2 C2 -176.6(2) . . . . ? O3 C16 O4 C17 0.6(4) . . . . ? C15 C16 O4 C17 177.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 28.14 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.185 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.033