# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 846859' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H27 Br N2 O3' _chemical_formula_weight 579.48 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' Br Br -0.2901 2.4595 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.654(11) _cell_length_b 8.990(8) _cell_length_c 14.054(13) _cell_angle_alpha 90.00 _cell_angle_beta 108.273(17) _cell_angle_gamma 90.00 _cell_volume 1398(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 1.507 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8576 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0907 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 28.08 _reflns_number_total 5970 _reflns_number_gt 3721 _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^)+(0.0113P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(7) _refine_ls_number_reflns 5970 _refine_ls_number_parameters 352 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0798 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 0.843 _refine_ls_restrained_S_all 0.843 _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 Br1 Br -0.18792(3) 0.68525(5) 0.19302(2) 0.06930(13) Uani 1 1 d . . . O1 O 0.3912(2) 1.0428(3) 0.17439(17) 0.0690(7) Uani 1 1 d . . . O2 O 0.4714(2) 0.7976(3) 0.51807(17) 0.0774(7) Uani 1 1 d . . . O3 O 0.2264(3) 1.1881(5) 0.5206(2) 0.1063(9) Uani 1 1 d . . . N1 N 0.1975(2) 0.9549(3) 0.14577(16) 0.0445(6) Uani 1 1 d . . . N2 N 0.3473(2) 0.9817(3) 0.5385(2) 0.0602(7) Uani 1 1 d . . . C1 C -0.0177(3) 0.9303(3) -0.1042(2) 0.0520(8) Uani 1 1 d . . . H1 H -0.0695 1.0036 -0.0950 0.062 Uiso 1 1 calc R . . C2 C -0.0562(3) 0.8365(4) -0.1861(2) 0.0635(10) Uani 1 1 d . . . H2 H -0.1334 0.8471 -0.2315 0.076 Uiso 1 1 calc R . . C3 C 0.0191(4) 0.7286(4) -0.2002(3) 0.0705(12) Uani 1 1 d . . . H3 H -0.0063 0.6671 -0.2561 0.085 Uiso 1 1 calc R . . C4 C 0.1326(3) 0.7101(5) -0.1320(3) 0.0760(11) Uani 1 1 d . . . H4 H 0.1830 0.6349 -0.1410 0.091 Uiso 1 1 calc R . . C5 C 0.1712(3) 0.8040(4) -0.0498(3) 0.0652(10) Uani 1 1 d . . . H5 H 0.2477 0.7913 -0.0038 0.078 Uiso 1 1 calc R . . C6 C 0.0969(3) 0.9165(3) -0.0356(2) 0.0472(8) Uani 1 1 d . . . C7 C 0.1408(3) 1.0267(3) 0.0493(2) 0.0508(8) Uani 1 1 d . . . H7A H 0.1987 1.0935 0.0349 0.061 Uiso 1 1 calc R . . H7B H 0.0730 1.0858 0.0535 0.061 Uiso 1 1 calc R . . C8 C 0.1387(2) 0.8613(3) 0.1956(2) 0.0411(7) Uani 1 1 d . . . C9 C 0.0170(3) 0.8283(4) 0.1668(2) 0.0442(7) Uani 1 1 d . . . H9 H -0.0369 0.8671 0.1085 0.053 Uiso 1 1 calc R . . C10 C -0.0205(2) 0.7341(3) 0.2295(2) 0.0490(8) Uani 1 1 d . . . C11 C 0.0566(2) 0.6782(5) 0.3165(2) 0.0552(7) Uani 1 1 d . . . H11 H 0.0276 0.6169 0.3571 0.066 Uiso 1 1 calc R . . C12 C 0.1799(3) 0.7139(4) 0.3440(2) 0.0544(9) Uani 1 1 d . . . H12 H 0.2336 0.6747 0.4022 0.065 Uiso 1 1 calc R . . C13 C 0.2206(2) 0.8075(3) 0.2840(2) 0.0426(7) Uani 1 1 d . . . C14 C 0.3182(3) 0.9682(4) 0.1987(2) 0.0501(8) Uani 1 1 d . . . C15 C 0.3435(2) 0.8718(3) 0.2940(2) 0.0453(8) Uani 1 1 d . . . C16 C 0.4424(3) 0.7555(4) 0.2971(2) 0.0579(9) Uani 1 1 d . . . H16A H 0.5188 0.8073 0.3100 0.069 Uiso 1 1 calc R . . H16B H 0.4499 0.6894 0.3533 0.069 Uiso 1 1 calc R . . C17 C 0.4227(2) 0.6622(4) 0.2048(2) 0.0541(8) Uani 1 1 d . . . C18 C 0.3540(3) 0.5337(4) 0.1887(3) 0.0753(11) Uani 1 1 d . . . H18 H 0.3158 0.5050 0.2348 0.090 Uiso 1 1 calc R . . C19 C 0.3415(4) 0.4468(5) 0.1039(5) 0.1055(17) Uani 1 1 d . . . H19 H 0.2938 0.3617 0.0931 0.127 Uiso 1 1 calc R . . C20 C 0.3984(4) 0.4856(7) 0.0374(4) 0.1035(16) Uani 1 1 d . . . H20 H 0.3902 0.4263 -0.0186 0.124 Uiso 1 1 calc R . . C21 C 0.4673(4) 0.6098(6) 0.0514(4) 0.0954(14) Uani 1 1 d . . . H21 H 0.5068 0.6349 0.0054 0.114 Uiso 1 1 calc R . . C22 C 0.4795(3) 0.7005(6) 0.1346(3) 0.0710(10) Uani 1 1 d . . . H22 H 0.5256 0.7868 0.1432 0.085 Uiso 1 1 calc R . . C23 C 0.4100(3) 0.9050(4) 0.4858(2) 0.0575(9) Uani 1 1 d . . . C24 C 0.3888(3) 0.9804(3) 0.3853(2) 0.0515(8) Uani 1 1 d . . . H24 H 0.4654 1.0242 0.3841 0.062 Uiso 1 1 calc R . . C25 C 0.3010(3) 1.1080(4) 0.3860(3) 0.0630(10) Uani 1 1 d . . . H25A H 0.3349 1.2028 0.3755 0.076 Uiso 1 1 calc R . . H25B H 0.2246 1.0938 0.3336 0.076 Uiso 1 1 calc R . . C26 C 0.2834(3) 1.1036(4) 0.4874(3) 0.0683(10) Uani 1 1 d . . . C27 C 0.3447(3) 0.9342(5) 0.6383(3) 0.0748(11) Uani 1 1 d . . . H27A H 0.3119 1.0138 0.6685 0.090 Uiso 1 1 calc R . . H27B H 0.4266 0.9148 0.6810 0.090 Uiso 1 1 calc R . . C28 C 0.2696(3) 0.7968(5) 0.6318(3) 0.0597(10) Uani 1 1 d . . . C29 C 0.1476(4) 0.7978(6) 0.5833(3) 0.0759(12) Uani 1 1 d . . . H29 H 0.1093 0.8859 0.5563 0.091 Uiso 1 1 calc R . . C30 C 0.0805(4) 0.6663(9) 0.5744(3) 0.0950(14) Uani 1 1 d . . . H30 H -0.0022 0.6670 0.5411 0.114 Uiso 1 1 calc R . . C31 C 0.1360(7) 0.5382(7) 0.6144(4) 0.1078(19) Uani 1 1 d . . . H31 H 0.0919 0.4504 0.6073 0.129 Uiso 1 1 calc R . . C32 C 0.2565(6) 0.5382(7) 0.6651(5) 0.1131(18) Uani 1 1 d . . . H32 H 0.2940 0.4508 0.6943 0.136 Uiso 1 1 calc R . . C33 C 0.3218(4) 0.6637(8) 0.6733(3) 0.0905(13) Uani 1 1 d . . . H33 H 0.4042 0.6611 0.7078 0.109 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 Br1 0.04804(16) 0.0896(3) 0.0751(2) -0.0200(2) 0.02639(14) -0.0172(2) O1 0.0555(14) 0.0707(16) 0.0727(16) 0.0131(13) 0.0084(12) -0.0224(13) O2 0.0731(16) 0.0929(18) 0.0591(16) 0.0211(14) 0.0107(12) 0.0321(16) O3 0.109(2) 0.0902(19) 0.120(2) -0.024(3) 0.0374(17) 0.023(3) N1 0.0451(14) 0.0423(14) 0.0395(14) 0.0030(12) 0.0039(11) -0.0071(12) N2 0.0560(17) 0.0604(19) 0.0581(18) -0.0091(16) 0.0089(14) -0.0054(16) C1 0.0567(19) 0.0405(18) 0.054(2) 0.0029(16) 0.0096(16) -0.0015(16) C2 0.070(2) 0.056(2) 0.053(2) 0.0019(18) 0.0023(18) -0.006(2) C3 0.089(3) 0.077(3) 0.049(2) -0.0141(19) 0.027(2) -0.019(2) C4 0.077(2) 0.082(3) 0.077(2) -0.021(3) 0.036(2) 0.007(2) C5 0.054(2) 0.078(3) 0.059(2) -0.010(2) 0.0108(17) 0.007(2) C6 0.0552(18) 0.0416(18) 0.0438(18) 0.0053(15) 0.0140(15) -0.0050(16) C7 0.0567(18) 0.0443(18) 0.0449(18) 0.0049(15) 0.0065(15) -0.0039(15) C8 0.0437(16) 0.0345(16) 0.0420(17) -0.0018(14) 0.0091(14) -0.0026(14) C9 0.0428(16) 0.0459(18) 0.0394(17) -0.0072(15) 0.0063(13) -0.0020(14) C10 0.0438(16) 0.053(2) 0.0511(19) -0.0155(15) 0.0166(15) -0.0059(14) C11 0.0604(17) 0.0584(18) 0.0489(17) -0.005(2) 0.0199(14) -0.016(2) C12 0.0566(17) 0.055(3) 0.0437(17) 0.0054(17) 0.0040(14) -0.0054(17) C13 0.0435(16) 0.0394(18) 0.0399(17) 0.0002(14) 0.0059(14) -0.0046(14) C14 0.0487(18) 0.0437(19) 0.0527(19) -0.0008(17) 0.0084(15) -0.0085(17) C15 0.0386(16) 0.0410(18) 0.0490(18) 0.0017(14) 0.0033(13) -0.0063(14) C16 0.0420(17) 0.059(2) 0.067(2) 0.0074(17) 0.0085(16) 0.0013(15) C17 0.0397(14) 0.046(2) 0.072(2) -0.003(2) 0.0118(14) 0.0014(17) C18 0.063(2) 0.061(2) 0.105(3) -0.001(2) 0.031(2) -0.001(2) C19 0.087(3) 0.066(3) 0.165(5) -0.046(3) 0.041(3) -0.015(3) C20 0.088(3) 0.111(4) 0.115(4) -0.046(3) 0.037(3) 0.008(3) C21 0.083(3) 0.102(4) 0.113(4) -0.013(3) 0.048(3) 0.009(3) C22 0.0606(18) 0.070(3) 0.087(3) -0.004(3) 0.0300(18) 0.003(2) C23 0.0413(17) 0.066(2) 0.054(2) -0.0012(19) -0.0021(16) -0.0022(18) C24 0.0451(17) 0.0479(19) 0.0512(19) -0.0010(16) 0.0001(14) -0.0057(15) C25 0.0573(19) 0.0433(18) 0.068(2) -0.0058(16) -0.0095(17) -0.0017(16) C26 0.063(2) 0.059(2) 0.075(3) -0.022(2) 0.009(2) -0.005(2) C27 0.072(2) 0.095(3) 0.053(2) -0.019(2) 0.0132(19) -0.010(2) C28 0.060(2) 0.075(3) 0.045(2) -0.0081(19) 0.0178(18) 0.008(2) C29 0.061(3) 0.105(3) 0.058(3) 0.010(2) 0.015(2) -0.003(2) C30 0.076(2) 0.149(5) 0.060(2) -0.010(4) 0.0203(19) -0.035(4) C31 0.152(6) 0.100(4) 0.096(4) -0.025(4) 0.074(4) -0.038(4) C32 0.125(5) 0.102(4) 0.138(5) 0.031(4) 0.077(4) 0.029(4) C33 0.071(2) 0.108(4) 0.103(3) 0.014(4) 0.042(2) 0.021(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 Br1 C10 1.906(3) . ? O1 C14 1.213(3) . ? O2 C23 1.203(4) . ? O3 C26 1.195(5) . ? N1 C14 1.376(4) . ? N1 C8 1.403(4) . ? N1 C7 1.459(4) . ? N2 C23 1.378(4) . ? N2 C26 1.391(5) . ? N2 C27 1.475(5) . ? C1 C2 1.382(4) . ? C1 C6 1.387(4) . ? C1 H1 0.9300 . ? C2 C3 1.364(5) . ? C2 H2 0.9300 . ? C3 C4 1.379(5) . ? C3 H3 0.9300 . ? C4 C5 1.386(5) . ? C4 H4 0.9300 . ? C5 C6 1.386(5) . ? C5 H5 0.9300 . ? C6 C7 1.511(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.379(4) . ? C8 C13 1.395(4) . ? C9 C10 1.389(4) . ? C9 H9 0.9300 . ? C10 C11 1.366(4) . ? C11 C12 1.403(4) . ? C11 H11 0.9300 . ? C12 C13 1.377(4) . ? C12 H12 0.9300 . ? C13 C15 1.510(4) . ? C14 C15 1.544(4) . ? C15 C16 1.547(4) . ? C15 C24 1.567(4) . ? C16 C17 1.500(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.383(5) . ? C17 C22 1.393(5) . ? C18 C19 1.393(6) . ? C18 H18 0.9300 . ? C19 C20 1.351(7) . ? C19 H19 0.9300 . ? C20 C21 1.354(6) . ? C20 H20 0.9300 . ? C21 C22 1.396(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.515(5) . ? C24 C25 1.539(4) . ? C24 H24 0.9800 . ? C25 C26 1.503(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C27 C28 1.500(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.371(5) . ? C28 C33 1.385(7) . ? C29 C30 1.402(7) . ? C29 H29 0.9300 . ? C30 C31 1.353(8) . ? C30 H30 0.9300 . ? C31 C32 1.361(8) . ? C31 H31 0.9300 . ? C32 C33 1.346(8) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? 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 C14 N1 C8 111.1(2) . . ? C14 N1 C7 123.5(3) . . ? C8 N1 C7 125.4(2) . . ? C23 N2 C26 113.9(3) . . ? C23 N2 C27 122.6(3) . . ? C26 N2 C27 123.4(3) . . ? C2 C1 C6 121.0(3) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C5 119.7(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 120.7(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 118.3(3) . . ? C5 C6 C7 121.3(3) . . ? C1 C6 C7 120.3(3) . . ? N1 C7 C6 112.7(3) . . ? N1 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C13 122.7(3) . . ? C9 C8 N1 126.9(3) . . ? C13 C8 N1 110.3(3) . . ? C8 C9 C10 116.4(3) . . ? C8 C9 H9 121.8 . . ? C10 C9 H9 121.8 . . ? C11 C10 C9 122.9(3) . . ? C11 C10 Br1 119.1(3) . . ? C9 C10 Br1 118.0(2) . . ? C10 C11 C12 119.5(3) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 119.4(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C8 119.1(3) . . ? C12 C13 C15 132.5(3) . . ? C8 C13 C15 108.3(3) . . ? O1 C14 N1 125.8(3) . . ? O1 C14 C15 126.5(3) . . ? N1 C14 C15 107.7(3) . . ? C13 C15 C14 102.5(2) . . ? C13 C15 C16 114.9(2) . . ? C14 C15 C16 110.0(3) . . ? C13 C15 C24 112.4(3) . . ? C14 C15 C24 106.5(2) . . ? C16 C15 C24 110.0(2) . . ? C17 C16 C15 116.3(2) . . ? C17 C16 H16A 108.2 . . ? C15 C16 H16A 108.2 . . ? C17 C16 H16B 108.2 . . ? C15 C16 H16B 108.2 . . ? H16A C16 H16B 107.4 . . ? C18 C17 C22 118.0(3) . . ? C18 C17 C16 122.2(3) . . ? C22 C17 C16 119.8(3) . . ? C17 C18 C19 120.6(4) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.3(4) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 120.6(5) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C20 C21 C22 120.2(5) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C17 C22 C21 120.2(4) . . ? C17 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? O2 C23 N2 123.5(3) . . ? O2 C23 C24 127.9(3) . . ? N2 C23 C24 108.6(3) . . ? C23 C24 C25 104.0(3) . . ? C23 C24 C15 113.5(3) . . ? C25 C24 C15 114.6(2) . . ? C23 C24 H24 108.2 . . ? C25 C24 H24 108.2 . . ? C15 C24 H24 108.2 . . ? C26 C25 C24 106.0(3) . . ? C26 C25 H25A 110.5 . . ? C24 C25 H25A 110.5 . . ? C26 C25 H25B 110.5 . . ? C24 C25 H25B 110.5 . . ? H25A C25 H25B 108.7 . . ? O3 C26 N2 124.9(4) . . ? O3 C26 C25 127.6(4) . . ? N2 C26 C25 107.4(3) . . ? N2 C27 C28 111.4(3) . . ? N2 C27 H27A 109.3 . . ? C28 C27 H27A 109.3 . . ? N2 C27 H27B 109.3 . . ? C28 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? C29 C28 C33 117.7(4) . . ? C29 C28 C27 121.3(4) . . ? C33 C28 C27 121.0(4) . . ? C28 C29 C30 120.1(4) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C31 C30 C29 120.0(4) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C32 119.9(6) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C33 C32 C31 120.5(6) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C28 121.8(4) . . ? C32 C33 H33 119.1 . . ? C28 C33 H33 119.1 . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 28.08 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.223 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.043