# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef '- rut01pub.cif' _audit_update_record ; 2012-05-01 # Formatted by publCIF ; # 1. SUBMISSION DETAILS _publ_contact_author ; Dr. Peter J. Rutledge School of Chemistry F11 The University of Sydney NSW 2006 Australia ; _publ_contact_author_phone +61293515020 _publ_contact_author_fax +61293513329 _publ_contact_author_email peter.rutledge@sydney.edu.au _publ_requested_coeditor_name ? # 2. TITLE AND AUTHOR LIST _publ_section_title ; Investigating the cis-Dihydroxylation of Alkenes by Non-Heme Iron Enzyme Mimics ; loop_ _publ_author_name _publ_author_address 'Sarah M. Barry' ; Department of Chemistry University of Warwick Coventry CV4 7AL UK ; H.Muller-Bunz ; School of Chemistry and Chemical Biology University College Dublin Belfield Dublin 4 Ireland ; 'Peter J. Rutledge' ; School of Chemistry F11 The University of Sydney NSW 2006 Australia ; _publ_contact_author_name 'Dr. Peter J. Rutledge' #===END_data_global #TrackingRef '- rut01pub.cif' data_rut01(11) _database_code_depnum_ccdc_archive 'CCDC 879768' #TrackingRef '- rut01pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 Br N O3' _chemical_formula_sum 'C20 H22 Br N O3' _chemical_formula_weight 404.30 _chemical_absolute_configuration ad 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' Br Br -0.2901 2.4595 '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_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.8965(17) _cell_length_b 8.9206(15) _cell_length_c 11.355(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.274(2) _cell_angle_gamma 90.00 _cell_volume 920.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4209 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 28.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.80 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 2.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1088 _exptl_absorpt_correction_T_max 0.3991 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2000) was used for absorption correction. R(int) for selected reflections was 0.165 before and 0.074 after correction. The Ratio of minimum to maximum transmission is 0.272647. An additional spherical absorption correction for \m*r=1.0 was applied. The \l/2 correction factor is 0.0015. ; _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7231 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0688 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3936 _reflns_number_gt 3429 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0518P)^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 0.047(10) _refine_ls_number_reflns 3936 _refine_ls_number_parameters 229 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.007 _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 Br1 Br 0.09260(4) 0.04990(6) 1.02933(3) 0.03421(13) Uani 1 1 d . . . C1 C -0.0116(4) -0.0297(4) 0.8570(3) 0.0206(7) Uani 1 1 d . . . H1A H 0.0570 -0.0892 0.8318 0.025 Uiso 1 1 calc R . . H1B H -0.0917 -0.0968 0.8561 0.025 Uiso 1 1 calc R . . C2 C -0.0752(4) 0.0955(3) 0.7627(3) 0.0153(7) Uani 1 1 d . . . C3 C -0.1910(4) 0.1818(4) 0.7629(3) 0.0190(7) Uani 1 1 d . . . H3 H -0.2307 0.1666 0.8257 0.023 Uiso 1 1 calc R . . C4 C -0.2482(4) 0.2913(4) 0.6693(3) 0.0224(8) Uani 1 1 d . . . H4 H -0.3297 0.3506 0.6653 0.027 Uiso 1 1 calc R . . C5 C -0.1839(4) 0.3125(4) 0.5814(3) 0.0191(7) Uani 1 1 d . . . H5 H -0.2214 0.3858 0.5158 0.023 Uiso 1 1 calc R . . C6 C -0.0648(4) 0.2252(4) 0.5914(3) 0.0150(7) Uani 1 1 d . . . C7 C 0.0177(4) 0.2477(4) 0.5053(3) 0.0158(7) Uani 1 1 d . . . H7A H -0.0321 0.3266 0.4416 0.019 Uiso 1 1 calc R . . H7B H 0.0144 0.1536 0.4581 0.019 Uiso 1 1 calc R . . C8 C 0.1793(4) 0.2929(3) 0.5806(3) 0.0122(6) Uani 1 1 d . . . C9 C 0.2614(4) 0.3161(4) 0.4922(3) 0.0146(7) Uani 1 1 d . . . C10 C 0.2493(4) 0.2086(4) 0.3984(3) 0.0183(7) Uani 1 1 d . . . H10 H 0.1848 0.1257 0.3855 0.022 Uiso 1 1 calc R . . C11 C 0.3315(4) 0.2235(4) 0.3249(3) 0.0205(7) Uani 1 1 d . . . H11 H 0.3232 0.1502 0.2617 0.025 Uiso 1 1 calc R . . C12 C 0.4262(4) 0.3446(4) 0.3423(3) 0.0187(7) Uani 1 1 d . . . H12 H 0.4839 0.3528 0.2927 0.022 Uiso 1 1 calc R . . C13 C 0.4356(4) 0.4530(4) 0.4324(3) 0.0200(7) Uani 1 1 d . . . H13 H 0.4979 0.5374 0.4431 0.024 Uiso 1 1 calc R . . C14 C 0.3538(4) 0.4385(4) 0.5076(3) 0.0167(7) Uani 1 1 d . . . H14 H 0.3614 0.5129 0.5698 0.020 Uiso 1 1 calc R . . C15 C 0.2646(4) 0.1758(4) 0.6837(3) 0.0145(6) Uani 1 1 d . . . C16 C 0.2282(4) 0.3828(3) 0.7858(3) 0.0137(6) Uani 1 1 d . . . H16 H 0.1362 0.3730 0.8018 0.016 Uiso 1 1 calc R . . C17 C 0.3303(4) 0.4958(4) 0.8792(3) 0.0162(7) Uani 1 1 d . . . C18 C 0.4796(4) 0.5043(4) 0.8675(3) 0.0240(8) Uani 1 1 d . . . H18A H 0.5256 0.4049 0.8832 0.036 Uiso 1 1 calc R . . H18B H 0.5436 0.5754 0.9307 0.036 Uiso 1 1 calc R . . H18C H 0.4648 0.5378 0.7811 0.036 Uiso 1 1 calc R . . C19 C 0.3530(4) 0.4444(4) 1.0147(3) 0.0233(8) Uani 1 1 d . . . H19A H 0.2586 0.4456 1.0237 0.035 Uiso 1 1 calc R . . H19B H 0.4219 0.5124 1.0779 0.035 Uiso 1 1 calc R . . H19C H 0.3931 0.3425 1.0290 0.035 Uiso 1 1 calc R . . C20 C 0.2554(5) 0.6492(4) 0.8506(4) 0.0273(9) Uani 1 1 d . . . H20A H 0.2428 0.6813 0.7643 0.041 Uiso 1 1 calc R . . H20B H 0.3164 0.7223 0.9136 0.041 Uiso 1 1 calc R . . H20C H 0.1589 0.6424 0.8555 0.041 Uiso 1 1 calc R . . N N -0.0122(3) 0.1152(3) 0.6792(3) 0.0148(6) Uani 1 1 d . . . O1 O 0.3045(2) 0.0536(3) 0.66869(18) 0.0180(4) Uani 1 1 d . . . O2 O 0.2984(3) 0.2380(2) 0.8000(2) 0.0153(5) Uani 1 1 d . . . O4 O 0.1912(2) 0.4249(2) 0.65530(19) 0.0134(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 Br1 0.0390(2) 0.0363(2) 0.01899(17) 0.0043(2) 0.00255(14) 0.0022(2) C1 0.0282(19) 0.0197(18) 0.0164(16) 0.0034(13) 0.0114(14) 0.0013(16) C2 0.0200(16) 0.0083(15) 0.0183(16) -0.0004(11) 0.0081(13) -0.0053(12) C3 0.0238(18) 0.0155(16) 0.0189(17) 0.0018(13) 0.0097(14) -0.0006(14) C4 0.027(2) 0.0166(17) 0.0247(18) -0.0001(14) 0.0110(16) 0.0037(15) C5 0.0266(19) 0.0122(16) 0.0184(17) 0.0020(13) 0.0087(15) -0.0011(15) C6 0.0187(17) 0.0092(15) 0.0155(15) -0.0018(12) 0.0051(13) -0.0051(13) C7 0.0211(18) 0.0124(15) 0.0128(14) -0.0011(12) 0.0055(13) -0.0017(14) C8 0.0191(17) 0.0062(14) 0.0127(14) -0.0013(11) 0.0076(13) 0.0002(12) C9 0.0219(18) 0.0111(15) 0.0121(15) 0.0025(12) 0.0080(14) 0.0018(13) C10 0.0266(19) 0.0120(17) 0.0172(16) 0.0003(12) 0.0095(14) -0.0005(14) C11 0.029(2) 0.0212(18) 0.0115(15) -0.0015(13) 0.0088(14) 0.0050(15) C12 0.0202(17) 0.0262(19) 0.0126(15) 0.0046(13) 0.0095(13) 0.0040(15) C13 0.0222(18) 0.0224(19) 0.0156(16) 0.0033(13) 0.0078(14) -0.0041(15) C14 0.0217(18) 0.0155(16) 0.0131(15) -0.0004(12) 0.0071(13) 0.0008(14) C15 0.0200(16) 0.0139(16) 0.0133(14) 0.0017(12) 0.0105(13) -0.0020(14) C16 0.0231(17) 0.0074(15) 0.0136(15) -0.0009(12) 0.0104(13) 0.0014(13) C17 0.0262(18) 0.0096(14) 0.0119(15) -0.0052(11) 0.0066(14) -0.0024(13) C18 0.0272(19) 0.026(2) 0.0208(17) -0.0036(13) 0.0113(14) -0.0051(14) C19 0.032(2) 0.0231(18) 0.0151(17) -0.0067(14) 0.0097(15) -0.0042(16) C20 0.042(2) 0.0087(17) 0.025(2) -0.0036(14) 0.0060(17) -0.0009(16) N 0.0190(14) 0.0098(13) 0.0149(13) -0.0004(10) 0.0061(11) -0.0016(11) O1 0.0293(11) 0.0092(9) 0.0187(10) 0.0007(12) 0.0130(8) 0.0054(13) O2 0.0253(13) 0.0071(10) 0.0128(10) 0.0003(8) 0.0070(9) 0.0034(9) O4 0.0235(13) 0.0062(10) 0.0105(10) -0.0012(8) 0.0066(9) 0.0005(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 Br1 C1 1.949(3) . ? C1 C2 1.502(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N 1.337(4) . ? C2 C3 1.382(5) . ? C3 C4 1.389(5) . ? C3 H3 0.9500 . ? C4 C5 1.392(5) . ? C4 H4 0.9500 . ? C5 C6 1.380(5) . ? C5 H5 0.9500 . ? C6 N 1.348(4) . ? C6 C7 1.514(5) . ? C7 C8 1.540(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O4 1.429(4) . ? C8 C9 1.534(4) . ? C8 C15 1.548(4) . ? C9 C14 1.391(5) . ? C9 C10 1.403(5) . ? C10 C11 1.383(5) . ? C10 H10 0.9500 . ? C11 C12 1.392(5) . ? C11 H11 0.9500 . ? C12 C13 1.384(5) . ? C12 H12 0.9500 . ? C13 C14 1.396(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 O1 1.195(4) . ? C15 O2 1.347(4) . ? C16 O4 1.429(4) . ? C16 O2 1.446(4) . ? C16 C17 1.522(4) . ? C16 H16 1.0000 . ? C17 C20 1.529(5) . ? C17 C19 1.534(5) . ? C17 C18 1.537(5) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C2 C1 Br1 110.6(2) . . ? C2 C1 H1A 109.5 . . ? Br1 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? Br1 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? N C2 C3 123.2(3) . . ? N C2 C1 115.0(3) . . ? C3 C2 C1 121.8(3) . . ? C2 C3 C4 118.6(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C3 C4 C5 118.7(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 118.8(3) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? N C6 C5 122.6(3) . . ? N C6 C7 115.2(3) . . ? C5 C6 C7 122.2(3) . . ? C6 C7 C8 112.5(3) . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? O4 C8 C9 109.6(2) . . ? O4 C8 C7 111.7(3) . . ? C9 C8 C7 112.0(3) . . ? O4 C8 C15 102.4(2) . . ? C9 C8 C15 108.3(3) . . ? C7 C8 C15 112.3(3) . . ? C14 C9 C10 119.1(3) . . ? C14 C9 C8 121.1(3) . . ? C10 C9 C8 119.8(3) . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.8(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 119.5(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 120.2(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C9 C14 C13 120.5(3) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? O1 C15 O2 123.2(3) . . ? O1 C15 C8 128.3(3) . . ? O2 C15 C8 108.3(3) . . ? O4 C16 O2 105.4(2) . . ? O4 C16 C17 112.1(3) . . ? O2 C16 C17 110.9(3) . . ? O4 C16 H16 109.4 . . ? O2 C16 H16 109.4 . . ? C17 C16 H16 109.4 . . ? C16 C17 C20 108.2(3) . . ? C16 C17 C19 107.2(3) . . ? C20 C17 C19 110.3(3) . . ? C16 C17 C18 111.6(3) . . ? C20 C17 C18 109.9(3) . . ? C19 C17 C18 109.7(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C2 N C6 117.9(3) . . ? C15 O2 C16 109.7(2) . . ? C8 O4 C16 109.1(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 Br1 C1 C2 N 111.1(3) . . . . ? Br1 C1 C2 C3 -69.4(4) . . . . ? N C2 C3 C4 2.2(5) . . . . ? C1 C2 C3 C4 -177.2(3) . . . . ? C2 C3 C4 C5 -1.8(5) . . . . ? C3 C4 C5 C6 -0.7(5) . . . . ? C4 C5 C6 N 3.2(5) . . . . ? C4 C5 C6 C7 -176.0(3) . . . . ? N C6 C7 C8 -61.8(4) . . . . ? C5 C6 C7 C8 117.4(3) . . . . ? C6 C7 C8 O4 -56.3(3) . . . . ? C6 C7 C8 C9 -179.7(3) . . . . ? C6 C7 C8 C15 58.1(3) . . . . ? O4 C8 C9 C14 11.3(4) . . . . ? C7 C8 C9 C14 135.9(3) . . . . ? C15 C8 C9 C14 -99.7(3) . . . . ? O4 C8 C9 C10 -172.0(3) . . . . ? C7 C8 C9 C10 -47.4(4) . . . . ? C15 C8 C9 C10 77.0(4) . . . . ? C14 C9 C10 C11 1.5(5) . . . . ? C8 C9 C10 C11 -175.3(3) . . . . ? C9 C10 C11 C12 -0.2(5) . . . . ? C10 C11 C12 C13 -1.4(5) . . . . ? C11 C12 C13 C14 1.8(5) . . . . ? C10 C9 C14 C13 -1.1(5) . . . . ? C8 C9 C14 C13 175.6(3) . . . . ? C12 C13 C14 C9 -0.5(5) . . . . ? O4 C8 C15 O1 -168.0(3) . . . . ? C9 C8 C15 O1 -52.2(4) . . . . ? C7 C8 C15 O1 72.0(4) . . . . ? O4 C8 C15 O2 7.6(3) . . . . ? C9 C8 C15 O2 123.4(3) . . . . ? C7 C8 C15 O2 -112.4(3) . . . . ? O4 C16 C17 C20 57.2(4) . . . . ? O2 C16 C17 C20 174.7(3) . . . . ? O4 C16 C17 C19 176.2(3) . . . . ? O2 C16 C17 C19 -66.3(3) . . . . ? O4 C16 C17 C18 -63.8(4) . . . . ? O2 C16 C17 C18 53.7(3) . . . . ? C3 C2 N C6 0.2(5) . . . . ? C1 C2 N C6 179.6(3) . . . . ? C5 C6 N C2 -2.9(5) . . . . ? C7 C6 N C2 176.3(3) . . . . ? O1 C15 O2 C16 -177.4(3) . . . . ? C8 C15 O2 C16 6.7(3) . . . . ? O4 C16 O2 C15 -18.7(3) . . . . ? C17 C16 O2 C15 -140.2(3) . . . . ? C9 C8 O4 C16 -134.1(3) . . . . ? C7 C8 O4 C16 101.2(3) . . . . ? C15 C8 O4 C16 -19.2(3) . . . . ? O2 C16 O4 C8 23.8(3) . . . . ? C17 C16 O4 C8 144.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.102 _refine_diff_density_min -0.802 _refine_diff_density_rms 0.122 #===END data_rut10z(12d) _database_code_depnum_ccdc_archive 'CCDC 879769' #TrackingRef '- rut01pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H32 N2 O3' _chemical_formula_sum 'C32 H32 N2 O3' _chemical_formula_weight 492.60 _chemical_absolute_configuration syn 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.0288(13) _cell_length_b 15.960(2) _cell_length_c 16.609(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2658.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 7664 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 28.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8218 _exptl_absorpt_correction_T_max 0.9616 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2000) was used for absorption correction. R(int) for selected reflections was 0.064 before and 0.023 after correction. The Ratio of minimum to maximum transmission is 0.854667. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; Friedel pairs were merged. ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41199 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0102 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2952 _reflns_number_gt 2877 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0464P)^2^+0.4995P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2952 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0740 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.72576(16) 0.46302(10) 1.06566(9) 0.0217(3) Uani 1 1 d . . . H1 H 0.7627 0.5212 1.0676 0.026 Uiso 1 1 calc R . . C2 C 0.65979(18) 0.44374(11) 1.14622(10) 0.0280(4) Uani 1 1 d . . . C3 C 0.6015(2) 0.35521(12) 1.14731(11) 0.0334(4) Uani 1 1 d . . . H3A H 0.5349 0.3498 1.1045 0.050 Uiso 1 1 calc R . . H3B H 0.5593 0.3447 1.1996 0.050 Uiso 1 1 calc R . . H3C H 0.6731 0.3144 1.1386 0.050 Uiso 1 1 calc R . . C4 C 0.7671(2) 0.45292(14) 1.21101(10) 0.0407(5) Uani 1 1 d . . . H4A H 0.8384 0.4122 1.2012 0.061 Uiso 1 1 calc R . . H4B H 0.7276 0.4427 1.2641 0.061 Uiso 1 1 calc R . . H4C H 0.8040 0.5097 1.2092 0.061 Uiso 1 1 calc R . . C5 C 0.5497(2) 0.50879(13) 1.16003(11) 0.0366(4) Uani 1 1 d . . . H5A H 0.5871 0.5652 1.1548 0.055 Uiso 1 1 calc R . . H5B H 0.5125 0.5017 1.2142 0.055 Uiso 1 1 calc R . . H5C H 0.4790 0.5010 1.1200 0.055 Uiso 1 1 calc R . . O1 O 0.63087(11) 0.45820(7) 1.00135(6) 0.0217(2) Uani 1 1 d . . . C6 C 0.68676(16) 0.41975(9) 0.93771(9) 0.0208(3) Uani 1 1 d . . . O2 O 0.63528(12) 0.41660(7) 0.87267(7) 0.0251(2) Uani 1 1 d . . . C7 C 0.81512(16) 0.37680(9) 0.96575(9) 0.0210(3) Uani 1 1 d . . . O3 O 0.83050(11) 0.40674(7) 1.04642(6) 0.0225(2) Uani 1 1 d . . . C8 C 0.79721(16) 0.28098(9) 0.96622(10) 0.0229(3) Uani 1 1 d . . . C9 C 0.85432(17) 0.23462(10) 1.02814(10) 0.0260(3) Uani 1 1 d . . . H9 H 0.9013 0.2623 1.0701 0.031 Uiso 1 1 calc R . . C10 C 0.84277(18) 0.14773(11) 1.02871(11) 0.0300(4) Uani 1 1 d . . . H10 H 0.8826 0.1161 1.0708 0.036 Uiso 1 1 calc R . . C11 C 0.77338(19) 0.10720(10) 0.96801(12) 0.0330(4) Uani 1 1 d . . . H11 H 0.7637 0.0480 0.9691 0.040 Uiso 1 1 calc R . . C12 C 0.7187(2) 0.15293(11) 0.90621(13) 0.0381(4) Uani 1 1 d . . . H12 H 0.6722 0.1251 0.8642 0.046 Uiso 1 1 calc R . . C13 C 0.73083(19) 0.23981(11) 0.90474(11) 0.0326(4) Uani 1 1 d . . . H13 H 0.6935 0.2709 0.8615 0.039 Uiso 1 1 calc R . . C14 C 0.93675(16) 0.39886(10) 0.91420(10) 0.0242(3) Uani 1 1 d . . . H14A H 1.0164 0.3723 0.9385 0.029 Uiso 1 1 calc R . . H14B H 0.9244 0.3742 0.8600 0.029 Uiso 1 1 calc R . . C15 C 0.96368(16) 0.49184(9) 0.90466(9) 0.0203(3) Uani 1 1 d . . . N1 N 0.86536(14) 0.54365(8) 0.92610(8) 0.0204(3) Uani 1 1 d . . . C16 C 1.08322(17) 0.52009(10) 0.87189(9) 0.0233(3) Uani 1 1 d . . . H16 H 1.1516 0.4818 0.8574 0.028 Uiso 1 1 calc R . . C17 C 1.10006(16) 0.60593(11) 0.86088(9) 0.0236(3) Uani 1 1 d . . . H17 H 1.1800 0.6272 0.8379 0.028 Uiso 1 1 calc R . . C18 C 0.99903(16) 0.65984(10) 0.88379(9) 0.0227(3) Uani 1 1 d . . . H18 H 1.0091 0.7187 0.8779 0.027 Uiso 1 1 calc R . . C19 C 0.88270(16) 0.62631(9) 0.91555(9) 0.0199(3) Uani 1 1 d . . . C20 C 0.76122(16) 0.67864(9) 0.93467(10) 0.0224(3) Uani 1 1 d . . . H20A H 0.6979 0.6744 0.8891 0.027 Uiso 1 1 calc R . . H20B H 0.7169 0.6548 0.9827 0.027 Uiso 1 1 calc R . . N2 N 0.78872(15) 0.76697(8) 0.94973(8) 0.0231(3) Uani 1 1 d . . . C21 C 0.84235(16) 0.79124(10) 1.02400(9) 0.0215(3) Uani 1 1 d . . . C22 C 0.89352(16) 0.87224(10) 1.03512(10) 0.0235(3) Uani 1 1 d . . . H22 H 0.8933 0.9108 0.9915 0.028 Uiso 1 1 calc R . . C23 C 0.94431(16) 0.89655(11) 1.10912(10) 0.0273(4) Uani 1 1 d . . . H23 H 0.9773 0.9519 1.1159 0.033 Uiso 1 1 calc R . . C24 C 0.94754(17) 0.84113(12) 1.17333(10) 0.0298(4) Uani 1 1 d . . . H24 H 0.9800 0.8586 1.2244 0.036 Uiso 1 1 calc R . . C25 C 0.90287(18) 0.76007(11) 1.16198(10) 0.0295(4) Uani 1 1 d . . . H25 H 0.9076 0.7210 1.2051 0.035 Uiso 1 1 calc R . . C26 C 0.85124(17) 0.73507(10) 1.08832(10) 0.0259(3) Uani 1 1 d . . . H26 H 0.8215 0.6790 1.0815 0.031 Uiso 1 1 calc R . . C27 C 0.73427(17) 0.82527(9) 0.89383(9) 0.0222(3) Uani 1 1 d . . . C28 C 0.65227(16) 0.89084(10) 0.91827(10) 0.0238(3) Uani 1 1 d . . . H28 H 0.6370 0.9002 0.9740 0.029 Uiso 1 1 calc R . . C29 C 0.59280(19) 0.94258(10) 0.86174(11) 0.0307(4) Uani 1 1 d . . . H29 H 0.5375 0.9874 0.8790 0.037 Uiso 1 1 calc R . . C30 C 0.6132(2) 0.92955(12) 0.78021(11) 0.0373(4) Uani 1 1 d . . . H30 H 0.5715 0.9647 0.7415 0.045 Uiso 1 1 calc R . . C31 C 0.6953(2) 0.86455(12) 0.75583(11) 0.0377(4) Uani 1 1 d . . . H31 H 0.7102 0.8554 0.7000 0.045 Uiso 1 1 calc R . . C32 C 0.75583(19) 0.81289(11) 0.81173(10) 0.0306(4) Uani 1 1 d . . . H32 H 0.8124 0.7688 0.7942 0.037 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 0.0243(7) 0.0203(7) 0.0205(7) 0.0008(6) -0.0016(6) 0.0003(6) C2 0.0317(9) 0.0329(9) 0.0194(7) 0.0029(6) 0.0014(7) 0.0031(8) C3 0.0364(10) 0.0350(9) 0.0288(8) 0.0109(7) 0.0054(8) 0.0001(8) C4 0.0423(11) 0.0606(12) 0.0191(8) 0.0011(8) -0.0020(8) 0.0003(10) C5 0.0401(11) 0.0426(10) 0.0272(8) 0.0006(8) 0.0100(8) 0.0075(9) O1 0.0233(5) 0.0229(5) 0.0188(5) 0.0019(4) -0.0001(4) 0.0023(5) C6 0.0247(8) 0.0152(6) 0.0223(7) 0.0026(6) 0.0016(6) -0.0018(6) O2 0.0305(6) 0.0238(5) 0.0209(5) 0.0015(4) -0.0052(5) 0.0025(5) C7 0.0245(8) 0.0186(7) 0.0199(7) 0.0001(6) -0.0024(6) -0.0008(6) O3 0.0240(5) 0.0225(5) 0.0209(5) -0.0008(4) -0.0027(5) 0.0022(4) C8 0.0223(7) 0.0191(7) 0.0271(8) 0.0009(6) 0.0028(7) 0.0004(6) C9 0.0278(8) 0.0239(7) 0.0264(8) 0.0001(7) 0.0016(7) 0.0035(7) C10 0.0318(9) 0.0262(8) 0.0320(9) 0.0076(7) 0.0085(8) 0.0085(7) C11 0.0333(9) 0.0174(7) 0.0483(10) 0.0014(7) 0.0084(8) -0.0006(7) C12 0.0397(10) 0.0250(8) 0.0496(11) -0.0069(8) -0.0105(9) -0.0033(8) C13 0.0372(10) 0.0249(8) 0.0356(9) 0.0008(7) -0.0100(8) 0.0004(8) C14 0.0254(8) 0.0196(7) 0.0276(8) -0.0014(6) 0.0040(7) 0.0020(6) C15 0.0230(7) 0.0207(7) 0.0172(7) -0.0009(6) -0.0018(6) 0.0002(6) N1 0.0230(6) 0.0189(6) 0.0192(6) -0.0011(5) 0.0001(5) -0.0017(5) C16 0.0226(7) 0.0268(8) 0.0205(7) -0.0025(6) -0.0013(6) 0.0028(7) C17 0.0197(7) 0.0298(8) 0.0214(7) 0.0011(6) -0.0018(6) -0.0046(7) C18 0.0250(8) 0.0201(7) 0.0229(7) 0.0013(6) -0.0046(7) -0.0046(6) C19 0.0233(7) 0.0197(7) 0.0167(7) -0.0016(6) -0.0044(6) -0.0003(6) C20 0.0229(7) 0.0192(7) 0.0250(7) -0.0018(6) -0.0028(6) -0.0007(6) N2 0.0299(7) 0.0164(6) 0.0231(6) -0.0010(5) -0.0037(6) 0.0019(6) C21 0.0194(7) 0.0220(7) 0.0231(7) -0.0027(6) 0.0007(6) 0.0034(6) C22 0.0205(7) 0.0228(7) 0.0273(8) -0.0019(6) 0.0032(7) -0.0002(6) C23 0.0190(7) 0.0308(8) 0.0321(9) -0.0089(7) 0.0020(7) -0.0026(7) C24 0.0208(8) 0.0438(10) 0.0250(8) -0.0096(7) -0.0030(7) 0.0035(8) C25 0.0291(8) 0.0348(9) 0.0245(8) 0.0018(7) -0.0022(7) 0.0080(7) C26 0.0286(8) 0.0217(7) 0.0275(8) -0.0001(7) -0.0013(7) 0.0034(7) C27 0.0246(8) 0.0195(7) 0.0225(7) 0.0006(6) -0.0018(6) -0.0029(6) C28 0.0270(8) 0.0198(7) 0.0245(7) 0.0008(6) -0.0009(7) -0.0028(7) C29 0.0327(9) 0.0196(8) 0.0397(9) 0.0045(7) -0.0070(8) -0.0005(7) C30 0.0471(11) 0.0308(9) 0.0339(9) 0.0134(8) -0.0124(9) -0.0054(8) C31 0.0511(12) 0.0394(10) 0.0225(8) 0.0051(7) -0.0024(9) -0.0058(9) C32 0.0364(9) 0.0309(8) 0.0243(8) -0.0020(7) 0.0016(7) 0.0004(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 O3 1.4186(19) . ? C1 O1 1.4327(19) . ? C1 C2 1.524(2) . ? C1 H1 1.0000 . ? C2 C4 1.529(3) . ? C2 C3 1.529(3) . ? C2 C5 1.533(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? O1 C6 1.3445(19) . ? C6 O2 1.1984(19) . ? C6 C7 1.531(2) . ? C7 O3 1.4308(18) . ? C7 C14 1.531(2) . ? C7 C8 1.540(2) . ? C8 C13 1.385(2) . ? C8 C9 1.390(2) . ? C9 C10 1.392(2) . ? C9 H9 0.9500 . ? C10 C11 1.385(3) . ? C10 H10 0.9500 . ? C11 C12 1.374(3) . ? C11 H11 0.9500 . ? C12 C13 1.392(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.517(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N1 1.335(2) . ? C15 C16 1.392(2) . ? N1 C19 1.342(2) . ? C16 C17 1.393(2) . ? C16 H16 0.9500 . ? C17 C18 1.383(2) . ? C17 H17 0.9500 . ? C18 C19 1.388(2) . ? C18 H18 0.9500 . ? C19 C20 1.511(2) . ? C20 N2 1.4580(19) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? N2 C21 1.400(2) . ? N2 C27 1.423(2) . ? C21 C26 1.398(2) . ? C21 C22 1.403(2) . ? C22 C23 1.386(2) . ? C22 H22 0.9500 . ? C23 C24 1.386(3) . ? C23 H23 0.9500 . ? C24 C25 1.382(3) . ? C24 H24 0.9500 . ? C25 C26 1.387(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.392(2) . ? C27 C32 1.395(2) . ? C28 C29 1.385(2) . ? C28 H28 0.9500 . ? C29 C30 1.385(3) . ? C29 H29 0.9500 . ? C30 C31 1.385(3) . ? C30 H30 0.9500 . ? C31 C32 1.382(3) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? 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 O3 C1 O1 106.85(12) . . ? O3 C1 C2 113.04(12) . . ? O1 C1 C2 110.82(13) . . ? O3 C1 H1 108.7 . . ? O1 C1 H1 108.7 . . ? C2 C1 H1 108.7 . . ? C1 C2 C4 107.04(15) . . ? C1 C2 C3 111.28(14) . . ? C4 C2 C3 110.43(15) . . ? C1 C2 C5 107.90(13) . . ? C4 C2 C5 109.68(15) . . ? C3 C2 C5 110.41(16) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 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 . . ? C6 O1 C1 109.49(12) . . ? O2 C6 O1 123.24(15) . . ? O2 C6 C7 128.15(14) . . ? O1 C6 C7 108.41(12) . . ? O3 C7 C6 103.06(12) . . ? O3 C7 C14 111.16(13) . . ? C6 C7 C14 113.37(12) . . ? O3 C7 C8 109.85(13) . . ? C6 C7 C8 110.37(13) . . ? C14 C7 C8 108.91(13) . . ? C1 O3 C7 110.04(11) . . ? C13 C8 C9 119.40(15) . . ? C13 C8 C7 121.57(15) . . ? C9 C8 C7 118.96(14) . . ? C8 C9 C10 120.07(16) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.14(17) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 119.76(16) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.49(18) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C8 C13 C12 120.11(17) . . ? C8 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C7 115.16(13) . . ? C15 C14 H14A 108.5 . . ? C7 C14 H14A 108.5 . . ? C15 C14 H14B 108.5 . . ? C7 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? N1 C15 C16 122.67(14) . . ? N1 C15 C14 116.53(14) . . ? C16 C15 C14 120.74(14) . . ? C15 N1 C19 118.57(14) . . ? C15 C16 C17 118.33(15) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C18 C17 C16 119.16(15) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 118.73(15) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? N1 C19 C18 122.53(15) . . ? N1 C19 C20 114.29(14) . . ? C18 C19 C20 123.00(14) . . ? N2 C20 C19 114.71(13) . . ? N2 C20 H20A 108.6 . . ? C19 C20 H20A 108.6 . . ? N2 C20 H20B 108.6 . . ? C19 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? C21 N2 C27 122.76(13) . . ? C21 N2 C20 119.42(13) . . ? C27 N2 C20 116.59(13) . . ? C26 C21 N2 121.37(14) . . ? C26 C21 C22 117.84(15) . . ? N2 C21 C22 120.75(14) . . ? C23 C22 C21 120.61(15) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 120.83(16) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C25 C24 C23 119.00(15) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 120.71(16) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C25 C26 C21 120.90(15) . . ? C25 C26 H26 119.5 . . ? C21 C26 H26 119.5 . . ? C28 C27 C32 118.90(15) . . ? C28 C27 N2 121.87(14) . . ? C32 C27 N2 119.06(15) . . ? C29 C28 C27 120.33(16) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C30 C29 C28 120.62(17) . . ? C30 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C31 C30 C29 119.09(17) . . ? C31 C30 H30 120.5 . . ? C29 C30 H30 120.5 . . ? C32 C31 C30 120.76(17) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C27 120.28(17) . . ? C31 C32 H32 119.9 . . ? C27 C32 H32 119.9 . . ? 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 O3 C1 C2 C4 61.73(18) . . . . ? O1 C1 C2 C4 -178.35(14) . . . . ? O3 C1 C2 C3 -59.01(18) . . . . ? O1 C1 C2 C3 60.90(17) . . . . ? O3 C1 C2 C5 179.72(14) . . . . ? O1 C1 C2 C5 -60.37(17) . . . . ? O3 C1 O1 C6 -14.99(15) . . . . ? C2 C1 O1 C6 -138.54(13) . . . . ? C1 O1 C6 O2 -170.50(14) . . . . ? C1 O1 C6 C7 14.33(16) . . . . ? O2 C6 C7 O3 176.96(15) . . . . ? O1 C6 C7 O3 -8.18(15) . . . . ? O2 C6 C7 C14 56.7(2) . . . . ? O1 C6 C7 C14 -128.44(13) . . . . ? O2 C6 C7 C8 -65.8(2) . . . . ? O1 C6 C7 C8 109.08(14) . . . . ? O1 C1 O3 C7 9.41(15) . . . . ? C2 C1 O3 C7 131.58(13) . . . . ? C6 C7 O3 C1 -1.12(15) . . . . ? C14 C7 O3 C1 120.65(13) . . . . ? C8 C7 O3 C1 -118.74(14) . . . . ? O3 C7 C8 C13 154.46(15) . . . . ? C6 C7 C8 C13 41.5(2) . . . . ? C14 C7 C8 C13 -83.58(19) . . . . ? O3 C7 C8 C9 -28.4(2) . . . . ? C6 C7 C8 C9 -141.41(15) . . . . ? C14 C7 C8 C9 93.52(17) . . . . ? C13 C8 C9 C10 -1.0(2) . . . . ? C7 C8 C9 C10 -178.19(16) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? C9 C10 C11 C12 1.5(3) . . . . ? C10 C11 C12 C13 -0.9(3) . . . . ? C9 C8 C13 C12 1.6(3) . . . . ? C7 C8 C13 C12 178.73(18) . . . . ? C11 C12 C13 C8 -0.7(3) . . . . ? O3 C7 C14 C15 -61.58(17) . . . . ? C6 C7 C14 C15 53.96(18) . . . . ? C8 C7 C14 C15 177.26(13) . . . . ? C7 C14 C15 N1 -14.3(2) . . . . ? C7 C14 C15 C16 168.39(13) . . . . ? C16 C15 N1 C19 0.0(2) . . . . ? C14 C15 N1 C19 -177.27(14) . . . . ? N1 C15 C16 C17 -0.3(2) . . . . ? C14 C15 C16 C17 176.90(14) . . . . ? C15 C16 C17 C18 0.9(2) . . . . ? C16 C17 C18 C19 -1.3(2) . . . . ? C15 N1 C19 C18 -0.5(2) . . . . ? C15 N1 C19 C20 174.77(13) . . . . ? C17 C18 C19 N1 1.1(2) . . . . ? C17 C18 C19 C20 -173.68(14) . . . . ? N1 C19 C20 N2 160.49(13) . . . . ? C18 C19 C20 N2 -24.3(2) . . . . ? C19 C20 N2 C21 -77.07(18) . . . . ? C19 C20 N2 C27 115.24(16) . . . . ? C27 N2 C21 C26 156.97(16) . . . . ? C20 N2 C21 C26 -9.9(2) . . . . ? C27 N2 C21 C22 -25.4(2) . . . . ? C20 N2 C21 C22 167.71(15) . . . . ? C26 C21 C22 C23 -3.5(2) . . . . ? N2 C21 C22 C23 178.82(14) . . . . ? C21 C22 C23 C24 1.0(2) . . . . ? C22 C23 C24 C25 1.9(2) . . . . ? C23 C24 C25 C26 -2.2(3) . . . . ? C24 C25 C26 C21 -0.4(3) . . . . ? N2 C21 C26 C25 -179.12(15) . . . . ? C22 C21 C26 C25 3.2(2) . . . . ? C21 N2 C27 C28 -42.8(2) . . . . ? C20 N2 C27 C28 124.41(17) . . . . ? C21 N2 C27 C32 141.84(17) . . . . ? C20 N2 C27 C32 -50.9(2) . . . . ? C32 C27 C28 C29 0.3(2) . . . . ? N2 C27 C28 C29 -175.06(15) . . . . ? C27 C28 C29 C30 0.4(3) . . . . ? C28 C29 C30 C31 -0.7(3) . . . . ? C29 C30 C31 C32 0.3(3) . . . . ? C30 C31 C32 C27 0.4(3) . . . . ? C28 C27 C32 C31 -0.7(3) . . . . ? N2 C27 C32 C31 174.78(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.236 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.032