# 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 'Miguel A Garcia-Garibay' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of California 405 Hilgard Avenue Los Angeles California 90095-1569 UNITED STATES OF AMERICA ; _publ_contact_author_email MGG@CHEM.UCLA.EDU _publ_section_title ; Diastereoselective Synthesis and Photodecarbonylation of di(3-Phenyl-2-pyrrolidinon-3-yl)ketones: Steps towards the Synthesis of Alkaloid Precursors with Adjacent Sterogenic Quaternary Centers ; loop_ _publ_author_name 'Miguel A Garcia-Garibay' 'Arunkumar Natarajan' 'Marino J. E. Resendiz' data_gg5006sg _database_code_depnum_ccdc_archive 'CCDC 656274' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H36 N2 O4' _chemical_formula_sum 'C36 H36 N2 O4' _chemical_formula_weight 560.67 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.277(6) _cell_length_b 10.860(6) _cell_length_c 16.533(8) _cell_angle_alpha 90.00 _cell_angle_beta 116.358(7) _cell_angle_gamma 90.00 _cell_volume 2940(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1197 _cell_measurement_theta_min 3.85 _cell_measurement_theta_max 22.79 _exptl_crystal_description cut-block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10804 _diffrn_reflns_av_R_equivalents 0.0790 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 27.40 _reflns_number_total 3301 _reflns_number_gt 2034 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0587P)^2^+0.9483P] 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 3301 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1085 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1428 _refine_ls_wR_factor_gt 0.1237 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.28502(10) 1.11869(13) 0.03426(11) 0.0287(4) Uani 1 1 d . . . O2 O 0.49185(10) 0.62595(13) 0.34585(11) 0.0272(4) Uani 1 1 d . . . N1 N 0.36186(12) 0.59233(15) 0.23741(13) 0.0233(4) Uani 1 1 d . . . C1 C 0.42362(14) 0.21805(19) 0.27550(16) 0.0238(5) Uani 1 1 d . . . H1 H 0.4110 0.2011 0.2143 0.029 Uiso 1 1 calc R . . C2 C 0.41589(15) 0.1252(2) 0.32919(17) 0.0295(6) Uani 1 1 d . . . H2 H 0.3980 0.0457 0.3043 0.035 Uiso 1 1 calc R . . C3 C 0.43400(15) 0.1476(2) 0.41802(17) 0.0304(6) Uani 1 1 d . . . H3 H 0.4284 0.0840 0.4543 0.036 Uiso 1 1 calc R . . C4 C 0.46045(14) 0.2637(2) 0.45415(16) 0.0286(6) Uani 1 1 d . . . H4 H 0.4729 0.2798 0.5154 0.034 Uiso 1 1 calc R . . C5 C 0.46882(14) 0.3566(2) 0.40095(15) 0.0231(5) Uani 1 1 d . . . H5 H 0.4878 0.4354 0.4267 0.028 Uiso 1 1 calc R . . C6 C 0.44977(14) 0.33605(19) 0.31040(15) 0.0218(5) Uani 1 1 d . . . C7 C 0.31520(14) 0.80799(19) 0.19383(16) 0.0244(5) Uani 1 1 d . . . C8 C 0.37626(15) 0.8402(2) 0.16952(16) 0.0272(6) Uani 1 1 d . . . H8 H 0.4241 0.7910 0.1897 0.033 Uiso 1 1 calc R . . C9 C 0.36877(14) 0.9432(2) 0.11623(16) 0.0263(5) Uani 1 1 d . . . H9 H 0.4114 0.9648 0.1008 0.032 Uiso 1 1 calc R . . C10 C 0.29838(14) 1.0139(2) 0.08590(16) 0.0249(5) Uani 1 1 d . . . C11 C 0.23591(14) 0.9809(2) 0.10765(16) 0.0278(6) Uani 1 1 d . . . H11 H 0.1872 1.0283 0.0858 0.033 Uiso 1 1 calc R . . C12 C 0.24457(15) 0.8792(2) 0.16105(16) 0.0282(6) Uani 1 1 d . . . H12 H 0.2016 0.8573 0.1757 0.034 Uiso 1 1 calc R . . C13 C 0.31679(14) 0.5100(2) 0.16215(16) 0.0261(5) Uani 1 1 d . . . H13A H 0.2841 0.5568 0.1062 0.031 Uiso 1 1 calc R . . H13B H 0.2801 0.4554 0.1754 0.031 Uiso 1 1 calc R . . C14 C 0.38459(13) 0.4361(2) 0.15365(15) 0.0228(5) Uani 1 1 d . . . H14A H 0.4003 0.4749 0.1094 0.027 Uiso 1 1 calc R . . H14B H 0.3667 0.3505 0.1344 0.027 Uiso 1 1 calc R . . C15 C 0.45662(13) 0.43878(19) 0.24972(15) 0.0202(5) Uani 1 1 d . . . C16 C 0.44108(14) 0.56391(19) 0.28410(15) 0.0215(5) Uani 1 1 d . . . C18 C 0.34601(15) 1.1524(2) 0.00706(17) 0.0294(6) Uani 1 1 d . . . H18A H 0.3980 1.1653 0.0606 0.044 Uiso 1 1 calc R . . H18B H 0.3298 1.2286 -0.0283 0.044 Uiso 1 1 calc R . . H18C H 0.3522 1.0865 -0.0299 0.044 Uiso 1 1 calc R . . C19 C 0.32537(15) 0.7005(2) 0.25673(17) 0.0272(6) Uani 1 1 d . . . H19A H 0.3600 0.7270 0.3196 0.033 Uiso 1 1 calc R . . H19B H 0.2712 0.6780 0.2521 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0280(10) 0.0199(8) 0.0378(10) 0.0045(7) 0.0144(9) 0.0044(7) O2 0.0289(10) 0.0206(8) 0.0299(9) -0.0056(7) 0.0110(8) -0.0026(7) N1 0.0235(11) 0.0159(9) 0.0296(11) -0.0031(8) 0.0110(10) 0.0006(8) C1 0.0248(13) 0.0225(12) 0.0245(13) -0.0041(10) 0.0114(12) -0.0017(9) C2 0.0304(15) 0.0211(11) 0.0379(15) 0.0002(11) 0.0161(13) -0.0042(10) C3 0.0310(15) 0.0301(13) 0.0346(15) 0.0073(11) 0.0185(13) -0.0027(11) C4 0.0304(15) 0.0337(13) 0.0229(13) 0.0007(11) 0.0129(12) 0.0006(11) C5 0.0223(13) 0.0208(11) 0.0262(13) -0.0016(10) 0.0107(11) -0.0011(9) C6 0.0197(12) 0.0188(11) 0.0279(13) -0.0003(10) 0.0115(11) -0.0008(9) C7 0.0258(13) 0.0182(11) 0.0285(13) -0.0059(10) 0.0114(12) 0.0002(9) C8 0.0239(13) 0.0213(11) 0.0363(15) -0.0013(11) 0.0133(12) 0.0035(10) C9 0.0234(13) 0.0241(12) 0.0329(14) -0.0005(11) 0.0138(12) 0.0009(10) C10 0.0250(13) 0.0193(11) 0.0268(13) -0.0041(10) 0.0082(11) -0.0004(9) C11 0.0210(13) 0.0230(12) 0.0371(15) -0.0013(11) 0.0107(12) 0.0059(10) C12 0.0245(13) 0.0253(12) 0.0388(15) -0.0039(11) 0.0174(12) -0.0018(10) C13 0.0220(13) 0.0242(12) 0.0282(13) -0.0021(10) 0.0076(11) -0.0015(10) C14 0.0234(13) 0.0198(11) 0.0248(12) -0.0021(10) 0.0102(11) 0.0011(9) C15 0.0207(12) 0.0152(10) 0.0236(12) -0.0022(9) 0.0088(11) -0.0012(9) C16 0.0234(13) 0.0170(10) 0.0234(12) 0.0002(10) 0.0099(11) -0.0007(9) C18 0.0320(14) 0.0244(12) 0.0340(14) -0.0007(11) 0.0165(13) 0.0024(10) C19 0.0273(14) 0.0218(11) 0.0362(15) -0.0036(10) 0.0174(13) 0.0015(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.378(3) . ? O1 C18 1.423(3) . ? O2 C16 1.231(3) . ? N1 C16 1.340(3) . ? N1 C13 1.455(3) . ? N1 C19 1.455(3) . ? C1 C2 1.392(3) . ? C1 C6 1.400(3) . ? C1 H1 0.9500 . ? C2 C3 1.376(3) . ? C2 H2 0.9500 . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C5 1.391(3) . ? C4 H4 0.9500 . ? C5 C6 1.396(3) . ? C5 H5 0.9500 . ? C6 C15 1.542(3) . ? C7 C8 1.388(3) . ? C7 C12 1.391(3) . ? C7 C19 1.519(3) . ? C8 C9 1.392(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.388(3) . ? C11 C12 1.379(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.534(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.549(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.547(3) . ? C15 C15 1.582(4) 2_655 ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O1 C18 117.39(17) . . ? C16 N1 C13 114.07(18) . . ? C16 N1 C19 122.88(19) . . ? C13 N1 C19 122.93(19) . . ? C2 C1 C6 120.9(2) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 119.5(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 121.1(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 117.7(2) . . ? C5 C6 C15 121.88(19) . . ? C1 C6 C15 120.4(2) . . ? C8 C7 C12 118.2(2) . . ? C8 C7 C19 121.5(2) . . ? C12 C7 C19 120.3(2) . . ? C7 C8 C9 121.3(2) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 119.2(2) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? O1 C10 C9 124.2(2) . . ? O1 C10 C11 115.7(2) . . ? C9 C10 C11 120.1(2) . . ? C12 C11 C10 119.9(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C7 121.2(2) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? N1 C13 C14 103.07(18) . . ? N1 C13 H13A 111.1 . . ? C14 C13 H13A 111.1 . . ? N1 C13 H13B 111.1 . . ? C14 C13 H13B 111.1 . . ? H13A C13 H13B 109.1 . . ? C13 C14 C15 104.46(17) . . ? 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 . . ? C6 C15 C16 108.37(17) . . ? C6 C15 C14 112.09(18) . . ? C16 C15 C14 100.49(17) . . ? C6 C15 C15 111.52(17) . 2_655 ? C16 C15 C15 110.18(13) . 2_655 ? C14 C15 C15 113.5(2) . 2_655 ? O2 C16 N1 125.1(2) . . ? O2 C16 C15 126.3(2) . . ? N1 C16 C15 108.56(18) . . ? O1 C18 H18A 109.5 . . ? O1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 C7 113.52(18) . . ? N1 C19 H19A 108.9 . . ? C7 C19 H19A 108.9 . . ? N1 C19 H19B 108.9 . . ? C7 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.1(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 C6 1.0(3) . . . . ? C4 C5 C6 C1 -1.3(3) . . . . ? C4 C5 C6 C15 178.4(2) . . . . ? C2 C1 C6 C5 0.9(3) . . . . ? C2 C1 C6 C15 -178.9(2) . . . . ? C12 C7 C8 C9 2.1(3) . . . . ? C19 C7 C8 C9 -176.1(2) . . . . ? C7 C8 C9 C10 -0.9(3) . . . . ? C18 O1 C10 C9 3.1(3) . . . . ? C18 O1 C10 C11 -177.2(2) . . . . ? C8 C9 C10 O1 178.8(2) . . . . ? C8 C9 C10 C11 -0.9(3) . . . . ? O1 C10 C11 C12 -178.3(2) . . . . ? C9 C10 C11 C12 1.4(3) . . . . ? C10 C11 C12 C7 -0.1(4) . . . . ? C8 C7 C12 C11 -1.6(3) . . . . ? C19 C7 C12 C11 176.6(2) . . . . ? C16 N1 C13 C14 -11.9(2) . . . . ? C19 N1 C13 C14 164.30(18) . . . . ? N1 C13 C14 C15 26.3(2) . . . . ? C5 C6 C15 C16 -29.4(3) . . . . ? C1 C6 C15 C16 150.3(2) . . . . ? C5 C6 C15 C14 -139.4(2) . . . . ? C1 C6 C15 C14 40.4(3) . . . . ? C5 C6 C15 C15 92.0(2) . . . 2_655 ? C1 C6 C15 C15 -88.2(3) . . . 2_655 ? C13 C14 C15 C6 85.1(2) . . . . ? C13 C14 C15 C16 -29.8(2) . . . . ? C13 C14 C15 C15 -147.44(12) . . . 2_655 ? C13 N1 C16 O2 174.2(2) . . . . ? C19 N1 C16 O2 -2.0(3) . . . . ? C13 N1 C16 C15 -7.9(2) . . . . ? C19 N1 C16 C15 175.90(18) . . . . ? C6 C15 C16 O2 83.9(3) . . . . ? C14 C15 C16 O2 -158.4(2) . . . . ? C15 C15 C16 O2 -38.4(3) 2_655 . . . ? C6 C15 C16 N1 -94.0(2) . . . . ? C14 C15 C16 N1 23.7(2) . . . . ? C15 C15 C16 N1 143.8(2) 2_655 . . . ? C16 N1 C19 C7 99.5(3) . . . . ? C13 N1 C19 C7 -76.4(3) . . . . ? C8 C7 C19 N1 -42.8(3) . . . . ? C12 C7 C19 N1 139.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.238 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.057 # Attachment 'gg5707s.cif' data_gg5707s _database_code_depnum_ccdc_archive 'CCDC 656275' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H36 N2 O5' _chemical_formula_sum 'C37 H36 N2 O5' _chemical_formula_weight 588.68 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.4881(18) _cell_length_b 10.8020(12) _cell_length_c 19.017(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.8700(10) _cell_angle_gamma 90.00 _cell_volume 3075.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5227 _cell_measurement_theta_min 3.823 _cell_measurement_theta_max 24.58 _exptl_crystal_description hexagon _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9167 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega and phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26136 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 27.89 _reflns_number_total 7275 _reflns_number_gt 4340 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0459P)^2^+0.5930P] 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 7275 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.05524(8) 0.30583(10) -0.00309(7) 0.0564(3) Uani 1 1 d . . . O3 O 0.89751(8) 0.06983(10) 0.04308(7) 0.0566(3) Uani 1 1 d . . . O2 O 0.78225(10) 0.19485(11) 0.12894(8) 0.0706(4) Uani 1 1 d . . . O4 O 1.52674(9) 0.41241(14) 0.20151(8) 0.0782(4) Uani 1 1 d . . . O5 O 0.55726(10) 0.87358(15) 0.06703(9) 0.0831(5) Uani 1 1 d . . . N1 N 1.15597(9) 0.16054(12) 0.05388(7) 0.0432(3) Uani 1 1 d . . . N2 N 0.80622(9) 0.40238(12) 0.12483(7) 0.0486(3) Uani 1 1 d . . . C1 C 1.08024(11) 0.22517(13) 0.04299(9) 0.0412(4) Uani 1 1 d . . . C2 C 1.02985(10) 0.18028(13) 0.09904(8) 0.0386(3) Uani 1 1 d . . . C3 C 1.07296(11) 0.05176(13) 0.11877(9) 0.0436(4) Uani 1 1 d . . . H3A H 1.0733 0.0285 0.1692 0.052 Uiso 1 1 calc R . . H3B H 1.0406 -0.0125 0.0851 0.052 Uiso 1 1 calc R . . C4 C 1.16753(11) 0.06789(15) 0.11099(9) 0.0474(4) Uani 1 1 d . . . H4A H 1.2082 0.0977 0.1569 0.057 Uiso 1 1 calc R . . H4B H 1.1911 -0.0105 0.0964 0.057 Uiso 1 1 calc R . . C5 C 1.22441(11) 0.18326(16) 0.01535(10) 0.0513(4) Uani 1 1 d . . . H5A H 1.1993 0.2356 -0.0278 0.062 Uiso 1 1 calc R . . H5B H 1.2430 0.1035 -0.0019 0.062 Uiso 1 1 calc R . . C6 C 1.30480(11) 0.24667(15) 0.06345(9) 0.0477(4) Uani 1 1 d . . . C7 C 1.38533(12) 0.18659(16) 0.08821(11) 0.0576(5) Uani 1 1 d . . . H7 H 1.3909 0.1032 0.0741 0.069 Uiso 1 1 calc R . . C8 C 1.45797(13) 0.24494(18) 0.13303(11) 0.0638(5) Uani 1 1 d . . . H8 H 1.5132 0.2021 0.1486 0.077 Uiso 1 1 calc R . . C9 C 1.45104(12) 0.36496(17) 0.15539(10) 0.0562(5) Uani 1 1 d . . . C10 C 1.37156(13) 0.42770(17) 0.13081(11) 0.0647(5) Uani 1 1 d . . . H10 H 1.3661 0.5109 0.1452 0.078 Uiso 1 1 calc R . . C11 C 1.30001(12) 0.36812(17) 0.08502(11) 0.0615(5) Uani 1 1 d . . . H11 H 1.2456 0.4121 0.0677 0.074 Uiso 1 1 calc R . . C12 C 1.52131(17) 0.5306(2) 0.23223(14) 0.0962(8) Uani 1 1 d . . . H12A H 1.5066 0.5927 0.1934 0.144 Uiso 1 1 calc R . . H12B H 1.5789 0.5512 0.2659 0.144 Uiso 1 1 calc R . . H12C H 1.4747 0.5298 0.2587 0.144 Uiso 1 1 calc R . . C13 C 0.92931(10) 0.17040(13) 0.06106(8) 0.0390(3) Uani 1 1 d . . . C14 C 0.86569(10) 0.28356(13) 0.04577(8) 0.0403(4) Uani 1 1 d . . . C15 C 0.90645(11) 0.41514(13) 0.05147(9) 0.0444(4) Uani 1 1 d . . . H15A H 0.9712 0.4123 0.0756 0.053 Uiso 1 1 calc R . . H15B H 0.8981 0.4519 0.0025 0.053 Uiso 1 1 calc R . . C16 C 0.85821(16) 0.48898(17) 0.09543(12) 0.0761(6) Uani 1 1 d . . . H16A H 0.9012 0.5329 0.1351 0.091 Uiso 1 1 calc R . . H16B H 0.8189 0.5509 0.0645 0.091 Uiso 1 1 calc R . . C17 C 0.81338(11) 0.28454(15) 0.10529(9) 0.0465(4) Uani 1 1 d . . . C18 C 0.75317(14) 0.44010(17) 0.17425(10) 0.0623(5) Uani 1 1 d . . . H18A H 0.7933 0.4554 0.2231 0.075 Uiso 1 1 calc R . . H18B H 0.7120 0.3722 0.1787 0.075 Uiso 1 1 calc R . . C19 C 0.69994(12) 0.55512(16) 0.14824(9) 0.0522(4) Uani 1 1 d . . . C20 C 0.72604(13) 0.66799(17) 0.17930(10) 0.0599(5) Uani 1 1 d . . . H20 H 0.7775 0.6725 0.2192 0.072 Uiso 1 1 calc R . . C21 C 0.67978(13) 0.77597(18) 0.15436(11) 0.0643(5) Uani 1 1 d . . . H21 H 0.6993 0.8528 0.1773 0.077 Uiso 1 1 calc R . . C22 C 0.60595(12) 0.77129(18) 0.09664(11) 0.0590(5) Uani 1 1 d . . . C23 C 0.57775(14) 0.6588(2) 0.06456(11) 0.0697(6) Uani 1 1 d . . . H23 H 0.5262 0.6548 0.0248 0.084 Uiso 1 1 calc R . . C24 C 0.62439(14) 0.55224(19) 0.09016(11) 0.0648(5) Uani 1 1 d . . . H24 H 0.6044 0.4753 0.0676 0.078 Uiso 1 1 calc R . . C25 C 0.59662(18) 0.9919(2) 0.08803(15) 0.0953(8) Uani 1 1 d . . . H25A H 0.5995 1.0069 0.1394 0.143 Uiso 1 1 calc R . . H25B H 0.5602 1.0564 0.0582 0.143 Uiso 1 1 calc R . . H25C H 0.6571 0.9937 0.0809 0.143 Uiso 1 1 calc R . . C26 C 0.80066(11) 0.26344(14) -0.02949(9) 0.0439(4) Uani 1 1 d . . . C27 C 0.71316(12) 0.22538(17) -0.03939(11) 0.0576(5) Uani 1 1 d . . . H27 H 0.6905 0.2102 0.0017 0.069 Uiso 1 1 calc R . . C28 C 0.65809(14) 0.20917(19) -0.10906(13) 0.0713(6) Uani 1 1 d . . . H28 H 0.5978 0.1841 -0.1151 0.086 Uiso 1 1 calc R . . C29 C 0.68987(15) 0.22906(19) -0.16901(12) 0.0707(6) Uani 1 1 d . . . H29 H 0.6521 0.2173 -0.2165 0.085 Uiso 1 1 calc R . . C30 C 0.77651(15) 0.26596(17) -0.15995(10) 0.0644(5) Uani 1 1 d . . . H30 H 0.7988 0.2801 -0.2014 0.077 Uiso 1 1 calc R . . C31 C 0.83196(13) 0.28293(16) -0.09094(9) 0.0535(4) Uani 1 1 d . . . H31 H 0.8921 0.3082 -0.0855 0.064 Uiso 1 1 calc R . . C32 C 1.04924(11) 0.26193(14) 0.16731(9) 0.0427(4) Uani 1 1 d . . . C33 C 1.10764(12) 0.36191(15) 0.17787(10) 0.0520(4) Uani 1 1 d . . . H33 H 1.1348 0.3853 0.1404 0.062 Uiso 1 1 calc R . . C34 C 1.12661(13) 0.42784(17) 0.24257(11) 0.0640(5) Uani 1 1 d . . . H34 H 1.1661 0.4966 0.2489 0.077 Uiso 1 1 calc R . . C35 C 1.08862(14) 0.3943(2) 0.29777(11) 0.0698(6) Uani 1 1 d . . . H35 H 1.1027 0.4387 0.3424 0.084 Uiso 1 1 calc R . . C36 C 1.03017(14) 0.29611(19) 0.28790(11) 0.0671(5) Uani 1 1 d . . . H36 H 1.0031 0.2733 0.3256 0.080 Uiso 1 1 calc R . . C37 C 1.01065(12) 0.23040(17) 0.22322(10) 0.0549(4) Uani 1 1 d . . . H37 H 0.9702 0.1627 0.2170 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0625(8) 0.0480(7) 0.0633(8) 0.0199(6) 0.0244(6) 0.0084(6) O3 0.0617(7) 0.0333(6) 0.0657(8) -0.0027(5) -0.0002(6) -0.0026(5) O2 0.0957(10) 0.0457(7) 0.0862(10) 0.0043(7) 0.0519(8) -0.0092(7) O4 0.0685(9) 0.0813(10) 0.0775(10) -0.0097(8) 0.0053(8) -0.0087(8) O5 0.0693(9) 0.0794(11) 0.0996(11) 0.0216(9) 0.0197(8) 0.0238(8) N1 0.0474(8) 0.0397(7) 0.0448(8) 0.0014(6) 0.0160(6) 0.0029(6) N2 0.0657(9) 0.0379(7) 0.0469(8) 0.0015(6) 0.0227(7) 0.0036(6) C1 0.0489(9) 0.0314(8) 0.0443(9) -0.0012(7) 0.0135(7) -0.0013(7) C2 0.0461(9) 0.0291(7) 0.0415(9) -0.0006(6) 0.0129(7) 0.0007(6) C3 0.0549(10) 0.0322(8) 0.0439(9) 0.0032(7) 0.0130(7) 0.0023(7) C4 0.0541(10) 0.0403(9) 0.0464(9) 0.0024(7) 0.0106(8) 0.0059(7) C5 0.0549(10) 0.0530(10) 0.0509(10) -0.0040(8) 0.0222(8) 0.0020(8) C6 0.0514(10) 0.0462(9) 0.0503(10) 0.0039(8) 0.0220(8) 0.0039(8) C7 0.0625(12) 0.0441(10) 0.0684(12) 0.0016(9) 0.0207(10) 0.0090(9) C8 0.0565(11) 0.0558(11) 0.0742(13) 0.0068(10) 0.0078(10) 0.0121(9) C9 0.0553(11) 0.0580(11) 0.0549(11) 0.0019(9) 0.0135(9) -0.0045(9) C10 0.0622(12) 0.0480(10) 0.0864(14) -0.0109(10) 0.0237(11) 0.0035(9) C11 0.0490(10) 0.0506(11) 0.0846(14) -0.0016(10) 0.0167(10) 0.0092(8) C12 0.0897(17) 0.113(2) 0.0911(17) -0.0458(15) 0.0326(14) -0.0262(15) C13 0.0512(9) 0.0304(8) 0.0362(8) 0.0000(6) 0.0127(7) -0.0028(7) C14 0.0463(9) 0.0316(8) 0.0437(9) 0.0025(6) 0.0129(7) 0.0009(6) C15 0.0484(9) 0.0313(8) 0.0528(10) 0.0042(7) 0.0115(8) 0.0023(7) C16 0.1166(18) 0.0408(10) 0.0910(15) -0.0097(10) 0.0635(14) -0.0112(11) C17 0.0534(10) 0.0386(9) 0.0483(10) 0.0035(7) 0.0148(8) -0.0001(7) C18 0.0900(14) 0.0547(11) 0.0491(11) 0.0027(8) 0.0305(10) 0.0106(10) C19 0.0639(11) 0.0525(10) 0.0461(10) 0.0004(8) 0.0248(9) 0.0056(8) C20 0.0616(11) 0.0597(11) 0.0553(11) -0.0048(9) 0.0093(9) 0.0090(9) C21 0.0647(12) 0.0546(11) 0.0710(13) -0.0108(10) 0.0128(10) 0.0058(9) C22 0.0533(11) 0.0618(12) 0.0651(12) 0.0076(10) 0.0211(9) 0.0115(9) C23 0.0627(12) 0.0798(15) 0.0606(13) 0.0038(11) 0.0048(10) -0.0031(11) C24 0.0782(14) 0.0587(12) 0.0574(12) -0.0065(9) 0.0171(11) -0.0088(10) C25 0.120(2) 0.0615(14) 0.110(2) 0.0058(13) 0.0382(16) 0.0327(14) C26 0.0488(9) 0.0322(8) 0.0501(10) 0.0023(7) 0.0117(8) 0.0049(7) C27 0.0492(10) 0.0573(11) 0.0643(12) -0.0004(9) 0.0111(9) 0.0009(8) C28 0.0498(11) 0.0709(14) 0.0841(16) -0.0070(12) 0.0005(11) 0.0019(10) C29 0.0729(14) 0.0639(13) 0.0623(13) -0.0044(10) -0.0064(11) 0.0118(11) C30 0.0832(15) 0.0574(11) 0.0496(11) 0.0022(9) 0.0116(10) 0.0045(10) C31 0.0597(11) 0.0496(10) 0.0504(11) 0.0019(8) 0.0125(9) -0.0009(8) C32 0.0474(9) 0.0363(8) 0.0436(9) -0.0037(7) 0.0103(7) 0.0033(7) C33 0.0570(11) 0.0417(9) 0.0567(11) -0.0060(8) 0.0138(9) -0.0035(8) C34 0.0658(12) 0.0471(10) 0.0723(13) -0.0180(9) 0.0053(10) -0.0009(9) C35 0.0763(14) 0.0701(13) 0.0575(12) -0.0255(10) 0.0069(11) 0.0143(11) C36 0.0768(13) 0.0760(14) 0.0525(12) -0.0123(10) 0.0241(10) 0.0088(11) C37 0.0601(11) 0.0552(10) 0.0518(11) -0.0069(8) 0.0187(9) -0.0017(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2259(18) . ? O3 C13 1.2055(17) . ? O2 C17 1.2185(19) . ? O4 C9 1.371(2) . ? O4 C12 1.416(3) . ? O5 C22 1.374(2) . ? O5 C25 1.429(3) . ? N1 C1 1.335(2) . ? N1 C4 1.4537(19) . ? N1 C5 1.456(2) . ? N2 C17 1.339(2) . ? N2 C16 1.438(2) . ? N2 C18 1.456(2) . ? C1 C2 1.551(2) . ? C2 C32 1.534(2) . ? C2 C13 1.543(2) . ? C2 C3 1.544(2) . ? C3 C4 1.519(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.507(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.377(2) . ? C6 C11 1.382(2) . ? C7 C8 1.377(3) . ? C7 H7 0.9500 . ? C8 C9 1.377(3) . ? C8 H8 0.9500 . ? C9 C10 1.378(3) . ? C10 C11 1.380(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.550(2) . ? C14 C26 1.540(2) . ? C14 C15 1.548(2) . ? C14 C17 1.552(2) . ? C15 C16 1.488(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C18 C19 1.503(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.370(2) . ? C19 C24 1.388(3) . ? C20 C21 1.387(3) . ? C20 H20 0.9500 . ? C21 C22 1.368(3) . ? C21 H21 0.9500 . ? C22 C23 1.379(3) . ? C23 C24 1.380(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.382(2) . ? C26 C31 1.391(2) . ? C27 C28 1.390(3) . ? C27 H27 0.9500 . ? C28 C29 1.370(3) . ? C28 H28 0.9500 . ? C29 C30 1.368(3) . ? C29 H29 0.9500 . ? C30 C31 1.384(3) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 C37 1.389(2) . ? C32 C33 1.390(2) . ? C33 C34 1.386(2) . ? C33 H33 0.9500 . ? C34 C35 1.377(3) . ? C34 H34 0.9500 . ? C35 C36 1.376(3) . ? C35 H35 0.9500 . ? C36 C37 1.385(2) . ? C36 H36 0.9500 . ? C37 H37 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 C9 O4 C12 118.01(17) . . ? C22 O5 C25 117.08(17) . . ? C1 N1 C4 114.26(13) . . ? C1 N1 C5 123.93(14) . . ? C4 N1 C5 121.74(13) . . ? C17 N2 C16 114.60(14) . . ? C17 N2 C18 123.08(14) . . ? C16 N2 C18 122.27(14) . . ? O1 C1 N1 125.91(15) . . ? O1 C1 C2 126.22(14) . . ? N1 C1 C2 107.87(13) . . ? C32 C2 C13 113.00(12) . . ? C32 C2 C3 109.43(12) . . ? C13 C2 C3 111.90(12) . . ? C32 C2 C1 112.20(12) . . ? C13 C2 C1 108.98(12) . . ? C3 C2 C1 100.69(12) . . ? C4 C3 C2 103.93(12) . . ? C4 C3 H3A 111.0 . . ? C2 C3 H3A 111.0 . . ? C4 C3 H3B 111.0 . . ? C2 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? N1 C4 C3 102.40(12) . . ? N1 C4 H4A 111.3 . . ? C3 C4 H4A 111.3 . . ? N1 C4 H4B 111.3 . . ? C3 C4 H4B 111.3 . . ? H4A C4 H4B 109.2 . . ? N1 C5 C6 111.47(13) . . ? N1 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N1 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C11 117.30(17) . . ? C7 C6 C5 121.86(16) . . ? C11 C6 C5 120.83(16) . . ? C6 C7 C8 121.34(17) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C9 C8 C7 120.38(17) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? O4 C9 C8 115.33(17) . . ? O4 C9 C10 125.18(18) . . ? C8 C9 C10 119.48(18) . . ? C9 C10 C11 119.17(17) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C10 C11 C6 122.29(17) . . ? C10 C11 H11 118.9 . . ? C6 C11 H11 118.9 . . ? O4 C12 H12A 109.5 . . ? O4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 C2 119.00(13) . . ? O3 C13 C14 117.62(14) . . ? C2 C13 C14 123.36(12) . . ? C26 C14 C15 110.65(12) . . ? C26 C14 C13 107.21(12) . . ? C15 C14 C13 118.87(13) . . ? C26 C14 C17 109.85(13) . . ? C15 C14 C17 102.86(12) . . ? C13 C14 C17 107.11(12) . . ? C16 C15 C14 106.09(14) . . ? C16 C15 H15A 110.5 . . ? C14 C15 H15A 110.5 . . ? C16 C15 H15B 110.5 . . ? C14 C15 H15B 110.5 . . ? H15A C15 H15B 108.7 . . ? N2 C16 C15 106.37(14) . . ? N2 C16 H16A 110.5 . . ? C15 C16 H16A 110.5 . . ? N2 C16 H16B 110.5 . . ? C15 C16 H16B 110.5 . . ? H16A C16 H16B 108.6 . . ? O2 C17 N2 125.79(16) . . ? O2 C17 C14 126.44(15) . . ? N2 C17 C14 107.75(13) . . ? N2 C18 C19 111.82(14) . . ? N2 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? N2 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C24 117.27(17) . . ? C20 C19 C18 121.18(17) . . ? C24 C19 C18 121.50(17) . . ? C19 C20 C21 122.12(18) . . ? C19 C20 H20 118.9 . . ? C21 C20 H20 118.9 . . ? C22 C21 C20 119.69(18) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 O5 123.84(19) . . ? C21 C22 C23 119.49(18) . . ? O5 C22 C23 116.67(18) . . ? C22 C23 C24 120.08(18) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C19 121.34(18) . . ? C23 C24 H24 119.3 . . ? C19 C24 H24 119.3 . . ? O5 C25 H25A 109.5 . . ? O5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C31 118.12(16) . . ? C27 C26 C14 123.60(16) . . ? C31 C26 C14 118.27(15) . . ? C26 C27 C28 120.51(19) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C29 C28 C27 120.6(2) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C30 C29 C28 119.44(19) . . ? C30 C29 H29 120.3 . . ? C28 C29 H29 120.3 . . ? C29 C30 C31 120.5(2) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C30 C31 C26 120.75(18) . . ? C30 C31 H31 119.6 . . ? C26 C31 H31 119.6 . . ? C37 C32 C33 118.15(15) . . ? C37 C32 C2 118.52(14) . . ? C33 C32 C2 123.22(15) . . ? C34 C33 C32 120.61(18) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C35 C34 C33 120.44(18) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C36 C35 C34 119.59(18) . . ? C36 C35 H35 120.2 . . ? C34 C35 H35 120.2 . . ? C35 C36 C37 120.17(19) . . ? C35 C36 H36 119.9 . . ? C37 C36 H36 119.9 . . ? C36 C37 C32 121.02(18) . . ? C36 C37 H37 119.5 . . ? C32 C37 H37 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 O1 -178.26(15) . . . . ? C5 N1 C1 O1 4.8(2) . . . . ? C4 N1 C1 C2 1.87(17) . . . . ? C5 N1 C1 C2 -175.04(13) . . . . ? O1 C1 C2 C32 -84.66(19) . . . . ? N1 C1 C2 C32 95.21(14) . . . . ? O1 C1 C2 C13 41.27(19) . . . . ? N1 C1 C2 C13 -138.86(13) . . . . ? O1 C1 C2 C3 159.07(15) . . . . ? N1 C1 C2 C3 -21.06(15) . . . . ? C32 C2 C3 C4 -87.01(15) . . . . ? C13 C2 C3 C4 146.95(13) . . . . ? C1 C2 C3 C4 31.31(15) . . . . ? C1 N1 C4 C3 18.62(17) . . . . ? C5 N1 C4 C3 -164.39(13) . . . . ? C2 C3 C4 N1 -30.74(15) . . . . ? C1 N1 C5 C6 105.66(17) . . . . ? C4 N1 C5 C6 -71.04(19) . . . . ? N1 C5 C6 C7 109.80(18) . . . . ? N1 C5 C6 C11 -69.6(2) . . . . ? C11 C6 C7 C8 0.4(3) . . . . ? C5 C6 C7 C8 -179.02(16) . . . . ? C6 C7 C8 C9 1.3(3) . . . . ? C12 O4 C9 C8 -173.74(19) . . . . ? C12 O4 C9 C10 6.4(3) . . . . ? C7 C8 C9 O4 178.22(17) . . . . ? C7 C8 C9 C10 -1.9(3) . . . . ? O4 C9 C10 C11 -179.25(18) . . . . ? C8 C9 C10 C11 0.9(3) . . . . ? C9 C10 C11 C6 0.8(3) . . . . ? C7 C6 C11 C10 -1.5(3) . . . . ? C5 C6 C11 C10 177.99(17) . . . . ? C32 C2 C13 O3 -132.68(15) . . . . ? C3 C2 C13 O3 -8.6(2) . . . . ? C1 C2 C13 O3 101.86(16) . . . . ? C32 C2 C13 C14 46.16(19) . . . . ? C3 C2 C13 C14 170.23(13) . . . . ? C1 C2 C13 C14 -79.30(16) . . . . ? O3 C13 C14 C26 -39.79(19) . . . . ? C2 C13 C14 C26 141.35(14) . . . . ? O3 C13 C14 C15 -166.11(14) . . . . ? C2 C13 C14 C15 15.0(2) . . . . ? O3 C13 C14 C17 78.07(17) . . . . ? C2 C13 C14 C17 -100.79(16) . . . . ? C26 C14 C15 C16 102.67(17) . . . . ? C13 C14 C15 C16 -132.66(16) . . . . ? C17 C14 C15 C16 -14.60(18) . . . . ? C17 N2 C16 C15 -0.8(2) . . . . ? C18 N2 C16 C15 176.76(16) . . . . ? C14 C15 C16 N2 10.2(2) . . . . ? C16 N2 C17 O2 172.72(19) . . . . ? C18 N2 C17 O2 -4.8(3) . . . . ? C16 N2 C17 C14 -9.0(2) . . . . ? C18 N2 C17 C14 173.47(14) . . . . ? C26 C14 C17 O2 74.9(2) . . . . ? C15 C14 C17 O2 -167.27(17) . . . . ? C13 C14 C17 O2 -41.2(2) . . . . ? C26 C14 C17 N2 -103.41(15) . . . . ? C15 C14 C17 N2 14.43(17) . . . . ? C13 C14 C17 N2 140.47(13) . . . . ? C17 N2 C18 C19 -137.06(17) . . . . ? C16 N2 C18 C19 45.6(2) . . . . ? N2 C18 C19 C20 -103.2(2) . . . . ? N2 C18 C19 C24 74.3(2) . . . . ? C24 C19 C20 C21 -0.1(3) . . . . ? C18 C19 C20 C21 177.53(18) . . . . ? C19 C20 C21 C22 -0.5(3) . . . . ? C20 C21 C22 O5 -178.31(18) . . . . ? C20 C21 C22 C23 0.8(3) . . . . ? C25 O5 C22 C21 13.3(3) . . . . ? C25 O5 C22 C23 -165.90(19) . . . . ? C21 C22 C23 C24 -0.7(3) . . . . ? O5 C22 C23 C24 178.54(18) . . . . ? C22 C23 C24 C19 0.1(3) . . . . ? C20 C19 C24 C23 0.3(3) . . . . ? C18 C19 C24 C23 -177.34(18) . . . . ? C15 C14 C26 C27 -125.78(16) . . . . ? C13 C14 C26 C27 103.16(17) . . . . ? C17 C14 C26 C27 -12.9(2) . . . . ? C15 C14 C26 C31 55.16(18) . . . . ? C13 C14 C26 C31 -75.90(17) . . . . ? C17 C14 C26 C31 168.04(14) . . . . ? C31 C26 C27 C28 -1.0(3) . . . . ? C14 C26 C27 C28 179.94(16) . . . . ? C26 C27 C28 C29 0.8(3) . . . . ? C27 C28 C29 C30 -0.4(3) . . . . ? C28 C29 C30 C31 0.1(3) . . . . ? C29 C30 C31 C26 -0.3(3) . . . . ? C27 C26 C31 C30 0.7(2) . . . . ? C14 C26 C31 C30 179.85(15) . . . . ? C13 C2 C32 C37 58.21(18) . . . . ? C3 C2 C32 C37 -67.21(18) . . . . ? C1 C2 C32 C37 -178.09(15) . . . . ? C13 C2 C32 C33 -125.62(16) . . . . ? C3 C2 C32 C33 108.97(17) . . . . ? C1 C2 C32 C33 -1.9(2) . . . . ? C37 C32 C33 C34 0.1(3) . . . . ? C2 C32 C33 C34 -176.12(15) . . . . ? C32 C33 C34 C35 0.8(3) . . . . ? C33 C34 C35 C36 -1.2(3) . . . . ? C34 C35 C36 C37 0.9(3) . . . . ? C35 C36 C37 C32 -0.1(3) . . . . ? C33 C32 C37 C36 -0.4(3) . . . . ? C2 C32 C37 C36 175.95(16) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.307 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.030