# 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 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Shi, Yian' _publ_author_name 'Yian Shi' _publ_contact_author_email yian@lamar.colostate.edu data_a _database_code_depnum_ccdc_archive 'CCDC 881889' #TrackingRef 'a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H38 N O3, C H4 O, Cl' _chemical_formula_sum 'C33 H42 Cl N O4' _chemical_formula_weight 552.13 _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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' '-x+1/2, y+1/2, -z+1/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 12.3304(17) _cell_length_b 12.3304(17) _cell_length_c 38.821(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5902.3(17) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 14931 _cell_measurement_theta_min 1.5737 _cell_measurement_theta_max 25.003 _exptl_crystal_description plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2368 _exptl_absorpt_coefficient_mu 0.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6720 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34943 _diffrn_reflns_av_R_equivalents 0.0990 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5205 _reflns_number_gt 5088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 2008)' _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^)+(0.0205P)^2^+9.8931P] 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 0.06(13) _refine_ls_number_reflns 5205 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0906 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1577 _refine_ls_goodness_of_fit_ref 1.321 _refine_ls_restrained_S_all 1.321 _refine_ls_shift/su_max 0.005 _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 Cl1 Cl 0.69407(10) 0.44242(9) 0.37274(3) 0.0267(3) Uani 1 1 d . . . O1 O 0.9424(3) 0.7082(3) 0.23282(8) 0.0329(8) Uani 1 1 d . . . O2 O 0.7954(3) 0.6098(3) 0.26795(9) 0.0330(9) Uani 1 1 d . . . O3 O 1.0573(3) 0.8408(3) 0.38614(9) 0.0314(8) Uani 1 1 d . . . H3 H 1.1072 0.8818 0.3793 0.038 Uiso 1 1 d R . . O4 O 0.3693(4) 0.5540(4) 0.39057(11) 0.0573(13) Uani 1 1 d . . . H4 H 0.4255 0.5811 0.3819 0.069 Uiso 1 1 d R . . N1 N 1.0193(3) 0.2376(3) 0.38931(9) 0.0238(9) Uani 1 1 d . . . H1 H 1.0638 0.1777 0.3859 0.029 Uiso 1 1 calc R . . C1 C 1.0196(4) 0.7685(5) 0.21312(13) 0.0354(13) Uani 1 1 d . . . H1C H 1.0270 0.8414 0.2228 0.053 Uiso 1 1 calc R . . H1A H 0.9948 0.7737 0.1892 0.053 Uiso 1 1 calc R . . H1B H 1.0900 0.7315 0.2138 0.053 Uiso 1 1 calc R . . C2 C 0.9651(4) 0.6960(4) 0.26711(12) 0.0263(11) Uani 1 1 d . . . C3 C 1.0588(4) 0.7333(4) 0.28327(12) 0.0246(11) Uani 1 1 d . . . H3A H 1.1133 0.7695 0.2704 0.030 Uiso 1 1 calc R . . C4 C 1.0719(4) 0.7170(4) 0.31856(12) 0.0208(10) Uani 1 1 d . . . C5 C 0.9937(4) 0.6619(4) 0.33735(12) 0.0201(10) Uani 1 1 d . . . C6 C 0.8994(4) 0.6243(4) 0.32153(12) 0.0225(11) Uani 1 1 d . . . H6 H 0.8461 0.5864 0.3345 0.027 Uiso 1 1 calc R . . C7 C 0.8843(4) 0.6429(4) 0.28653(13) 0.0266(11) Uani 1 1 d . . . C8 C 0.6998(4) 0.5888(5) 0.28603(14) 0.0388(14) Uani 1 1 d . . . H8C H 0.6836 0.6500 0.3013 0.058 Uiso 1 1 calc R . . H8B H 0.7086 0.5227 0.2998 0.058 Uiso 1 1 calc R . . H8A H 0.6400 0.5791 0.2697 0.058 Uiso 1 1 calc R . . C9 C 1.1643(4) 0.7522(4) 0.34142(13) 0.0270(12) Uani 1 1 d . . . H9B H 1.1865 0.8277 0.3363 0.032 Uiso 1 1 calc R . . H9A H 1.2277 0.7037 0.3389 0.032 Uiso 1 1 calc R . . C10 C 1.1147(4) 0.7431(4) 0.37747(14) 0.0269(11) Uani 1 1 d . . . H10 H 1.1715 0.7262 0.3951 0.032 Uiso 1 1 calc R . . C11 C 1.0308(4) 0.6499(4) 0.37478(12) 0.0211(10) Uani 1 1 d . . . C12 C 0.9450(4) 0.6490(4) 0.40302(12) 0.0259(11) Uani 1 1 d . . . H12A H 0.8796 0.6093 0.3953 0.031 Uiso 1 1 calc R . . H12B H 0.9240 0.7240 0.4093 0.031 Uiso 1 1 calc R . . C13 C 0.9982(4) 0.5914(4) 0.43367(13) 0.0293(12) Uani 1 1 d . . . H13B H 1.0400 0.6433 0.4479 0.035 Uiso 1 1 calc R . . H13A H 0.9429 0.5559 0.4483 0.035 Uiso 1 1 calc R . . C14 C 1.0723(4) 0.5083(4) 0.41734(12) 0.0243(11) Uani 1 1 d . . . H14 H 1.1334 0.4780 0.4313 0.029 Uiso 1 1 calc R . . C15 C 1.0941(4) 0.5430(4) 0.38074(13) 0.0229(11) Uani 1 1 d . . . H15 H 1.1692 0.5357 0.3712 0.028 Uiso 1 1 calc R . . C16 C 1.0285(4) 0.4424(4) 0.38743(12) 0.0255(11) Uani 1 1 d . . . H16 H 0.9488 0.4471 0.3830 0.031 Uiso 1 1 calc R . . C17 C 1.0834(4) 0.3361(4) 0.37887(12) 0.0233(11) Uani 1 1 d . . . H17A H 1.0965 0.3331 0.3537 0.028 Uiso 1 1 calc R . . H17B H 1.1548 0.3339 0.3905 0.028 Uiso 1 1 calc R . . C18 C 0.9188(4) 0.2210(4) 0.36697(12) 0.0269(12) Uani 1 1 d . . . H18A H 0.8915 0.1462 0.3704 0.032 Uiso 1 1 calc R . . H18B H 0.8614 0.2717 0.3746 0.032 Uiso 1 1 calc R . . C19 C 0.9402(4) 0.2389(4) 0.32911(13) 0.0303(12) Uani 1 1 d . . . C20 C 0.8959(4) 0.3262(4) 0.31255(13) 0.0328(13) Uani 1 1 d . . . H20 H 0.8511 0.3749 0.3251 0.039 Uiso 1 1 calc R . . C21 C 0.9145(5) 0.3453(5) 0.27793(15) 0.0453(16) Uani 1 1 d . . . H21 H 0.8847 0.4073 0.2669 0.054 Uiso 1 1 calc R . . C22 C 0.9765(6) 0.2734(5) 0.25992(15) 0.0531(18) Uani 1 1 d . . . H22 H 0.9877 0.2843 0.2360 0.064 Uiso 1 1 calc R . . C23 C 1.0226(5) 0.1862(5) 0.27578(14) 0.0473(17) Uani 1 1 d . . . H23 H 1.0674 0.1383 0.2629 0.057 Uiso 1 1 calc R . . C24 C 1.0047(5) 0.1669(5) 0.31046(13) 0.0385(14) Uani 1 1 d . . . H24 H 1.0359 0.1055 0.3214 0.046 Uiso 1 1 calc R . . C25 C 0.9890(4) 0.2394(4) 0.42799(11) 0.0252(11) Uani 1 1 d . . . H25 H 0.9518 0.3098 0.4329 0.030 Uiso 1 1 calc R . . C26 C 1.0924(5) 0.2353(4) 0.44984(13) 0.0339(13) Uani 1 1 d . . . H26A H 1.1370 0.1736 0.4426 0.051 Uiso 1 1 calc R . . H26C H 1.0730 0.2269 0.4742 0.051 Uiso 1 1 calc R . . H26B H 1.1334 0.3027 0.4468 0.051 Uiso 1 1 calc R . . C27 C 0.9123(4) 0.1488(4) 0.43781(12) 0.0268(11) Uani 1 1 d . . . C28 C 0.9468(5) 0.0412(4) 0.43795(13) 0.0315(12) Uani 1 1 d . . . H28 H 1.0178 0.0231 0.4303 0.038 Uiso 1 1 calc R . . C29 C 0.8774(5) -0.0389(5) 0.44923(16) 0.0467(16) Uani 1 1 d . . . H29 H 0.9015 -0.1120 0.4497 0.056 Uiso 1 1 calc R . . C30 C 0.7734(5) -0.0146(5) 0.45993(15) 0.0488(16) Uani 1 1 d . . . H30 H 0.7264 -0.0704 0.4679 0.059 Uiso 1 1 calc R . . C31 C 0.7389(5) 0.0907(6) 0.45893(16) 0.0516(17) Uani 1 1 d . . . H31 H 0.6669 0.1080 0.4657 0.062 Uiso 1 1 calc R . . C32 C 0.8081(5) 0.1728(5) 0.44806(14) 0.0369(14) Uani 1 1 d . . . H32 H 0.7834 0.2458 0.4477 0.044 Uiso 1 1 calc R . . C33 C 0.3624(5) 0.5756(5) 0.42620(15) 0.0494(17) Uani 1 1 d . . . H33A H 0.3355 0.5111 0.4382 0.074 Uiso 1 1 calc R . . H33B H 0.3125 0.6363 0.4301 0.074 Uiso 1 1 calc R . . H33C H 0.4345 0.5945 0.4350 0.074 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 Cl1 0.0288(7) 0.0231(6) 0.0283(6) -0.0017(5) 0.0009(5) -0.0002(5) O1 0.029(2) 0.042(2) 0.0279(18) 0.0048(17) -0.0004(17) -0.0045(17) O2 0.0229(19) 0.049(2) 0.0272(19) -0.0039(17) -0.0016(16) -0.0091(17) O3 0.030(2) 0.0208(18) 0.044(2) -0.0014(16) 0.0047(17) -0.0018(16) O4 0.047(3) 0.070(3) 0.055(3) -0.012(2) 0.013(2) -0.018(2) N1 0.028(2) 0.020(2) 0.023(2) 0.0028(17) 0.0008(18) 0.0019(17) C1 0.032(3) 0.044(4) 0.030(3) 0.005(3) 0.003(2) -0.001(2) C2 0.030(3) 0.031(3) 0.018(2) 0.007(2) 0.001(2) 0.000(2) C3 0.027(3) 0.019(2) 0.028(3) 0.005(2) 0.003(2) -0.002(2) C4 0.018(2) 0.016(2) 0.029(3) 0.003(2) -0.002(2) 0.0027(19) C5 0.015(2) 0.019(3) 0.027(3) -0.004(2) 0.002(2) 0.0017(19) C6 0.023(3) 0.015(2) 0.030(3) 0.001(2) 0.000(2) -0.0003(19) C7 0.028(3) 0.023(3) 0.030(3) -0.004(2) -0.007(2) 0.001(2) C8 0.024(3) 0.054(4) 0.038(3) -0.002(3) -0.005(3) -0.009(3) C9 0.012(2) 0.030(3) 0.039(3) 0.007(2) -0.002(2) -0.005(2) C10 0.033(3) 0.016(2) 0.032(3) 0.002(2) -0.002(2) 0.003(2) C11 0.025(3) 0.018(2) 0.020(2) 0.001(2) -0.002(2) -0.001(2) C12 0.022(3) 0.024(3) 0.031(3) 0.001(2) 0.002(2) 0.001(2) C13 0.034(3) 0.026(3) 0.028(3) -0.002(2) 0.003(2) -0.002(2) C14 0.026(3) 0.027(3) 0.020(2) 0.006(2) 0.000(2) -0.007(2) C15 0.020(2) 0.017(2) 0.032(3) 0.002(2) 0.001(2) -0.0037(19) C16 0.033(3) 0.018(2) 0.025(3) 0.003(2) 0.002(2) 0.002(2) C17 0.024(3) 0.022(3) 0.024(3) 0.003(2) -0.002(2) -0.0048(19) C18 0.029(3) 0.023(3) 0.029(3) -0.001(2) 0.000(2) -0.004(2) C19 0.026(3) 0.036(3) 0.029(3) -0.003(2) -0.003(2) 0.002(2) C20 0.032(3) 0.038(3) 0.028(3) -0.006(3) -0.005(2) 0.011(2) C21 0.052(4) 0.044(4) 0.040(3) 0.003(3) -0.007(3) 0.017(3) C22 0.075(5) 0.058(4) 0.026(3) 0.007(3) -0.002(3) 0.021(4) C23 0.055(4) 0.051(4) 0.036(3) -0.005(3) 0.004(3) 0.018(3) C24 0.054(4) 0.035(3) 0.026(3) 0.001(3) -0.008(3) 0.011(3) C25 0.034(3) 0.022(3) 0.020(2) -0.001(2) 0.003(2) 0.003(2) C26 0.046(4) 0.025(3) 0.031(3) -0.001(2) -0.002(3) -0.007(2) C27 0.034(3) 0.025(3) 0.022(3) -0.004(2) -0.004(2) -0.002(2) C28 0.034(3) 0.033(3) 0.028(3) -0.001(2) 0.003(2) -0.001(2) C29 0.064(4) 0.027(3) 0.049(4) 0.000(3) 0.003(3) -0.010(3) C30 0.052(4) 0.051(4) 0.044(4) -0.001(3) 0.002(3) -0.022(3) C31 0.042(4) 0.067(5) 0.046(4) -0.008(3) 0.012(3) -0.012(3) C32 0.033(3) 0.037(3) 0.041(3) -0.002(3) 0.002(3) -0.003(3) C33 0.045(4) 0.047(4) 0.057(4) -0.001(3) 0.007(3) -0.011(3) _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 C2 1.368(5) . ? O1 C1 1.429(6) . ? O2 C7 1.373(6) . ? O2 C8 1.397(6) . ? O3 C10 1.437(6) . ? O3 H3 0.8401 . ? O4 C33 1.411(7) . ? O4 H4 0.8402 . ? N1 C17 1.505(6) . ? N1 C18 1.526(6) . ? N1 C25 1.547(6) . ? N1 H1 0.9300 . ? C1 H1C 0.9800 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 C3 1.393(7) . ? C2 C7 1.411(7) . ? C3 C4 1.394(6) . ? C3 H3A 0.9500 . ? C4 C5 1.387(6) . ? C4 C9 1.508(7) . ? C5 C6 1.395(6) . ? C5 C11 1.530(7) . ? C6 C7 1.390(7) . ? C6 H6 0.9500 . ? C8 H8C 0.9800 . ? C8 H8B 0.9800 . ? C8 H8A 0.9800 . ? C9 C10 1.531(7) . ? C9 H9B 0.9900 . ? C9 H9A 0.9900 . ? C10 C11 1.549(7) . ? C10 H10 1.0000 . ? C11 C12 1.523(7) . ? C11 C15 1.550(6) . ? C12 C13 1.533(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.512(7) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 C15 1.508(6) . ? C14 C16 1.517(7) . ? C14 H14 1.0000 . ? C15 C16 1.503(6) . ? C15 H15 1.0000 . ? C16 C17 1.512(6) . ? C16 H16 1.0000 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.510(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.368(7) . ? C19 C24 1.394(7) . ? C20 C21 1.384(8) . ? C20 H20 0.9500 . ? C21 C22 1.363(8) . ? C21 H21 0.9500 . ? C22 C23 1.364(8) . ? C22 H22 0.9500 . ? C23 C24 1.385(7) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C27 1.513(7) . ? C25 C26 1.532(7) . ? C25 H25 1.0000 . ? C26 H26A 0.9800 . ? C26 H26C 0.9800 . ? C26 H26B 0.9800 . ? C27 C32 1.378(7) . ? C27 C28 1.394(7) . ? C28 C29 1.378(8) . ? C28 H28 0.9500 . ? C29 C30 1.381(9) . ? C29 H29 0.9500 . ? C30 C31 1.368(9) . ? C30 H30 0.9500 . ? C31 C32 1.389(8) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 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 O1 C1 116.2(4) . . ? C7 O2 C8 117.7(4) . . ? C10 O3 H3 94.0 . . ? C33 O4 H4 111.6 . . ? C17 N1 C18 112.4(3) . . ? C17 N1 C25 112.1(4) . . ? C18 N1 C25 111.0(4) . . ? C17 N1 H1 107.0 . . ? C18 N1 H1 107.0 . . ? C25 N1 H1 107.0 . . ? O1 C1 H1C 109.5 . . ? O1 C1 H1A 109.5 . . ? H1C C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1C C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C2 C3 124.8(4) . . ? O1 C2 C7 115.3(4) . . ? C3 C2 C7 119.9(4) . . ? C2 C3 C4 119.4(5) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 C4 C3 120.5(5) . . ? C5 C4 C9 110.9(4) . . ? C3 C4 C9 128.6(4) . . ? C4 C5 C6 120.7(4) . . ? C4 C5 C11 109.8(4) . . ? C6 C5 C11 129.4(4) . . ? C7 C6 C5 119.1(5) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? O2 C7 C6 124.8(5) . . ? O2 C7 C2 114.9(4) . . ? C6 C7 C2 120.3(5) . . ? O2 C8 H8C 109.5 . . ? O2 C8 H8B 109.5 . . ? H8C C8 H8B 109.5 . . ? O2 C8 H8A 109.5 . . ? H8C C8 H8A 109.5 . . ? H8B C8 H8A 109.5 . . ? C4 C9 C10 102.4(4) . . ? C4 C9 H9B 111.3 . . ? C10 C9 H9B 111.3 . . ? C4 C9 H9A 111.3 . . ? C10 C9 H9A 111.3 . . ? H9B C9 H9A 109.2 . . ? O3 C10 C9 110.4(4) . . ? O3 C10 C11 108.0(4) . . ? C9 C10 C11 105.0(4) . . ? O3 C10 H10 111.1 . . ? C9 C10 H10 111.1 . . ? C11 C10 H10 111.1 . . ? C12 C11 C5 118.5(4) . . ? C12 C11 C10 114.9(4) . . ? C5 C11 C10 101.1(4) . . ? C12 C11 C15 103.7(4) . . ? C5 C11 C15 112.0(4) . . ? C10 C11 C15 106.5(4) . . ? C11 C12 C13 105.4(4) . . ? C11 C12 H12A 110.7 . . ? C13 C12 H12A 110.7 . . ? C11 C12 H12B 110.7 . . ? C13 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C14 C13 C12 104.3(4) . . ? C14 C13 H13B 110.9 . . ? C12 C13 H13B 110.9 . . ? C14 C13 H13A 110.9 . . ? C12 C13 H13A 110.9 . . ? H13B C13 H13A 108.9 . . ? C15 C14 C13 108.1(4) . . ? C15 C14 C16 59.6(3) . . ? C13 C14 C16 117.9(4) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C16 C14 H14 118.8 . . ? C16 C15 C14 60.5(3) . . ? C16 C15 C11 117.1(4) . . ? C14 C15 C11 107.0(4) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C11 C15 H15 119.2 . . ? C15 C16 C17 115.9(4) . . ? C15 C16 C14 59.9(3) . . ? C17 C16 C14 118.3(4) . . ? C15 C16 H16 116.9 . . ? C17 C16 H16 116.9 . . ? C14 C16 H16 116.9 . . ? N1 C17 C16 113.9(4) . . ? N1 C17 H17A 108.8 . . ? C16 C17 H17A 108.8 . . ? N1 C17 H17B 108.8 . . ? C16 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C19 C18 N1 113.0(4) . . ? C19 C18 H18A 109.0 . . ? N1 C18 H18A 109.0 . . ? C19 C18 H18B 109.0 . . ? N1 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C24 119.0(5) . . ? C20 C19 C18 120.2(5) . . ? C24 C19 C18 120.8(5) . . ? C19 C20 C21 121.6(5) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C22 C21 C20 118.7(5) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C23 121.0(5) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C22 C23 C24 120.5(5) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C19 119.1(5) . . ? C23 C24 H24 120.4 . . ? C19 C24 H24 120.4 . . ? C27 C25 C26 110.9(4) . . ? C27 C25 N1 112.6(4) . . ? C26 C25 N1 109.7(4) . . ? C27 C25 H25 107.8 . . ? C26 C25 H25 107.8 . . ? N1 C25 H25 107.8 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? H26C C26 H26B 109.5 . . ? C32 C27 C28 119.2(5) . . ? C32 C27 C25 119.9(5) . . ? C28 C27 C25 120.9(5) . . ? C29 C28 C27 119.6(5) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C28 C29 C30 121.2(6) . . ? C28 C29 H29 119.4 . . ? C30 C29 H29 119.4 . . ? C31 C30 C29 119.1(6) . . ? C31 C30 H30 120.5 . . ? C29 C30 H30 120.5 . . ? C30 C31 C32 120.6(6) . . ? C30 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C27 C32 C31 120.3(6) . . ? C27 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? O4 C33 H33A 109.5 . . ? O4 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O4 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O1 C2 C3 -3.1(7) . . . . ? C1 O1 C2 C7 175.7(4) . . . . ? O1 C2 C3 C4 179.2(5) . . . . ? C7 C2 C3 C4 0.4(7) . . . . ? C2 C3 C4 C5 1.5(7) . . . . ? C2 C3 C4 C9 -178.4(5) . . . . ? C3 C4 C5 C6 -1.6(7) . . . . ? C9 C4 C5 C6 178.3(4) . . . . ? C3 C4 C5 C11 176.9(4) . . . . ? C9 C4 C5 C11 -3.2(5) . . . . ? C4 C5 C6 C7 -0.2(7) . . . . ? C11 C5 C6 C7 -178.4(5) . . . . ? C8 O2 C7 C6 22.0(7) . . . . ? C8 O2 C7 C2 -160.2(5) . . . . ? C5 C6 C7 O2 179.8(4) . . . . ? C5 C6 C7 C2 2.1(7) . . . . ? O1 C2 C7 O2 1.0(7) . . . . ? C3 C2 C7 O2 179.9(4) . . . . ? O1 C2 C7 C6 178.9(4) . . . . ? C3 C2 C7 C6 -2.2(8) . . . . ? C5 C4 C9 C10 -17.3(5) . . . . ? C3 C4 C9 C10 162.6(5) . . . . ? C4 C9 C10 O3 -85.8(5) . . . . ? C4 C9 C10 C11 30.4(5) . . . . ? C4 C5 C11 C12 148.3(4) . . . . ? C6 C5 C11 C12 -33.3(7) . . . . ? C4 C5 C11 C10 21.9(5) . . . . ? C6 C5 C11 C10 -159.8(5) . . . . ? C4 C5 C11 C15 -91.1(5) . . . . ? C6 C5 C11 C15 87.2(6) . . . . ? O3 C10 C11 C12 -42.7(6) . . . . ? C9 C10 C11 C12 -160.6(4) . . . . ? O3 C10 C11 C5 86.0(4) . . . . ? C9 C10 C11 C5 -31.8(5) . . . . ? O3 C10 C11 C15 -156.9(4) . . . . ? C9 C10 C11 C15 85.3(5) . . . . ? C5 C11 C12 C13 157.5(4) . . . . ? C10 C11 C12 C13 -83.0(5) . . . . ? C15 C11 C12 C13 32.7(5) . . . . ? C11 C12 C13 C14 -33.2(5) . . . . ? C12 C13 C14 C15 20.4(5) . . . . ? C12 C13 C14 C16 -44.1(6) . . . . ? C13 C14 C15 C16 -112.3(5) . . . . ? C13 C14 C15 C11 -0.3(5) . . . . ? C16 C14 C15 C11 112.0(4) . . . . ? C12 C11 C15 C16 45.0(5) . . . . ? C5 C11 C15 C16 -83.9(5) . . . . ? C10 C11 C15 C16 166.5(4) . . . . ? C12 C11 C15 C14 -20.0(5) . . . . ? C5 C11 C15 C14 -148.9(4) . . . . ? C10 C11 C15 C14 101.5(4) . . . . ? C14 C15 C16 C17 -109.1(5) . . . . ? C11 C15 C16 C17 155.9(4) . . . . ? C11 C15 C16 C14 -95.0(5) . . . . ? C13 C14 C16 C15 95.5(5) . . . . ? C15 C14 C16 C17 105.2(5) . . . . ? C13 C14 C16 C17 -159.3(4) . . . . ? C18 N1 C17 C16 70.9(5) . . . . ? C25 N1 C17 C16 -55.0(5) . . . . ? C15 C16 C17 N1 174.1(4) . . . . ? C14 C16 C17 N1 105.9(5) . . . . ? C17 N1 C18 C19 43.0(5) . . . . ? C25 N1 C18 C19 169.5(4) . . . . ? N1 C18 C19 C20 -111.3(5) . . . . ? N1 C18 C19 C24 69.0(6) . . . . ? C24 C19 C20 C21 -0.8(9) . . . . ? C18 C19 C20 C21 179.6(5) . . . . ? C19 C20 C21 C22 1.7(10) . . . . ? C20 C21 C22 C23 -2.3(11) . . . . ? C21 C22 C23 C24 2.0(11) . . . . ? C22 C23 C24 C19 -1.1(10) . . . . ? C20 C19 C24 C23 0.5(9) . . . . ? C18 C19 C24 C23 -179.9(5) . . . . ? C17 N1 C25 C27 172.4(4) . . . . ? C18 N1 C25 C27 45.8(5) . . . . ? C17 N1 C25 C26 -63.6(5) . . . . ? C18 N1 C25 C26 169.7(4) . . . . ? C26 C25 C27 C32 123.4(5) . . . . ? N1 C25 C27 C32 -113.3(5) . . . . ? C26 C25 C27 C28 -54.1(6) . . . . ? N1 C25 C27 C28 69.2(6) . . . . ? C32 C27 C28 C29 -1.9(8) . . . . ? C25 C27 C28 C29 175.6(5) . . . . ? C27 C28 C29 C30 1.0(9) . . . . ? C28 C29 C30 C31 0.6(10) . . . . ? C29 C30 C31 C32 -1.4(10) . . . . ? C28 C27 C32 C31 1.1(8) . . . . ? C25 C27 C32 C31 -176.5(5) . . . . ? C30 C31 C32 C27 0.6(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.227 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.054