# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Marcus Tius' 'Bradley O. Ashburn' 'Ashok K. Basak' 'William F. Bow' 'Naoyuki Shimada' 'David A. Vicic' _publ_contact_author_name 'Marcus Tius' _publ_contact_author_email TIUS@HAWAII.EDU _publ_section_title ; Organocatalytic Asymmetric Aza-Nazarov Cyclization of an Azirine ; # Attachment 'B927564A.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 773094' #TrackingRef 'B927564A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H33 N O7' _chemical_formula_weight 483.54 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.998(15) _cell_length_b 6.500(7) _cell_length_c 16.73(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.46(2) _cell_angle_gamma 90.00 _cell_volume 1299(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1551 _cell_measurement_theta_min 1.705 _cell_measurement_theta_max 31.921 _chemical_absolute_configuration rm _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9653 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_process_details Rigaku _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71075 _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 17444 _diffrn_reflns_av_R_equivalents 0.1821 _diffrn_reflns_av_sigmaI/netI 0.3767 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 32.72 _reflns_number_total 8691 _reflns_number_gt 2248 _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^)+(0.1023P)^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 8(3) _refine_ls_number_reflns 8691 _refine_ls_number_parameters 317 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.3463 _refine_ls_R_factor_gt 0.0997 _refine_ls_wR_factor_ref 0.3209 _refine_ls_wR_factor_gt 0.2014 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.934 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.8677(4) -0.2495(8) -0.3321(3) 0.0493(14) Uani 1 1 d . . . O2 O -0.7938(4) -0.7043(8) -0.2022(3) 0.0529(14) Uani 1 1 d . . . O3 O -0.9585(4) -0.5453(7) -0.2255(3) 0.0426(12) Uani 1 1 d . . . O4 O -0.6931(4) 0.0033(8) -0.3604(3) 0.0455(13) Uani 1 1 d . . . O5 O -0.6505(4) -0.3002(7) -0.4182(3) 0.0407(13) Uani 1 1 d . . . O6 O -0.6605(4) -0.1339(7) -0.5646(3) 0.0368(12) Uani 1 1 d . . . O7 O -0.6998(5) -0.1148(8) -0.6986(3) 0.0538(15) Uani 1 1 d . . . N1 N -0.6844(5) -0.3586(9) -0.1533(3) 0.0396(14) Uani 1 1 d . . . H1A H -0.6593 -0.4768 -0.1333 0.047 Uiso 1 1 calc R . . C1 C -0.7975(6) -0.3375(10) -0.1944(4) 0.0339(16) Uani 1 1 d . . . C2 C -0.7903(6) -0.2368(11) -0.2781(4) 0.0365(17) Uani 1 1 d . . . C3 C -0.6907(6) -0.1082(10) -0.2851(4) 0.0386(18) Uani 1 1 d . . . C4 C -0.6124(6) -0.0585(10) -0.2269(4) 0.0357(16) Uani 1 1 d . . . C5 C -0.6148(6) -0.1696(10) -0.1474(4) 0.0333(16) Uani 1 1 d . . . H5A H -0.6462 -0.0738 -0.1085 0.040 Uiso 1 1 calc R . . C6 C -0.8722(6) -0.1991(12) -0.1468(4) 0.0459(19) Uani 1 1 d . . . H6A H -0.8383 -0.0605 -0.1406 0.055 Uiso 1 1 calc R . . H6B H -0.9467 -0.1845 -0.1772 0.055 Uiso 1 1 calc R . . C7 C -0.8867(7) -0.2882(13) -0.0634(4) 0.052(2) Uani 1 1 d . . . H7A H -0.9350 -0.1973 -0.0352 0.078 Uiso 1 1 calc R . . H7B H -0.8133 -0.2992 -0.0325 0.078 Uiso 1 1 calc R . . H7C H -0.9209 -0.4249 -0.0692 0.078 Uiso 1 1 calc R . . C8 C -0.8474(6) -0.5474(13) -0.2066(4) 0.0431(18) Uani 1 1 d . . . C9 C -1.0192(6) -0.7385(13) -0.2351(5) 0.054(2) Uani 1 1 d . . . H9A H -0.9692 -0.8469 -0.2530 0.065 Uiso 1 1 calc R . . H9B H -1.0832 -0.7229 -0.2766 0.065 Uiso 1 1 calc R . . C10 C -1.0616(7) -0.8008(13) -0.1564(5) 0.062(2) Uani 1 1 d . . . H10A H -1.1024 -0.9312 -0.1634 0.093 Uiso 1 1 calc R . . H10B H -1.1118 -0.6941 -0.1392 0.093 Uiso 1 1 calc R . . H10C H -0.9980 -0.8177 -0.1156 0.093 Uiso 1 1 calc R . . C11 C -0.5259(7) 0.1090(12) -0.2329(4) 0.052(2) Uani 1 1 d . . . H11A H -0.5329 0.1656 -0.2874 0.078 Uiso 1 1 calc R . . H11B H -0.4508 0.0512 -0.2207 0.078 Uiso 1 1 calc R . . H11C H -0.5380 0.2186 -0.1944 0.078 Uiso 1 1 calc R . . C12 C -0.4971(5) -0.2346(10) -0.1125(4) 0.0327(16) Uani 1 1 d . . . C13 C -0.4307(6) -0.3616(12) -0.1562(4) 0.0417(18) Uani 1 1 d . . . H13A H -0.4597 -0.4117 -0.2074 0.050 Uiso 1 1 calc R . . C14 C -0.3244(7) -0.4144(13) -0.1260(5) 0.053(2) Uani 1 1 d . . . H14A H -0.2807 -0.5027 -0.1558 0.064 Uiso 1 1 calc R . . C15 C -0.2801(7) -0.3384(15) -0.0513(5) 0.058(2) Uani 1 1 d . . . H15A H -0.2062 -0.3746 -0.0306 0.070 Uiso 1 1 calc R . . C16 C -0.3438(6) -0.2107(12) -0.0073(4) 0.0465(19) Uani 1 1 d . . . H16A H -0.3142 -0.1580 0.0432 0.056 Uiso 1 1 calc R . . C17 C -0.4520(7) -0.1612(12) -0.0388(4) 0.047(2) Uani 1 1 d . . . H17A H -0.4962 -0.0744 -0.0088 0.056 Uiso 1 1 calc R . . C18 C -0.6738(6) -0.1193(11) -0.4236(4) 0.0339(16) Uani 1 1 d . . . C19 C -0.6804(5) 0.0147(10) -0.4990(4) 0.0293(15) Uani 1 1 d . . . C20 C -0.5943(5) 0.1878(10) -0.5007(4) 0.0357(17) Uani 1 1 d . . . H20A H -0.5175 0.1330 -0.5022 0.043 Uiso 1 1 calc R . . H20B H -0.5963 0.2807 -0.4539 0.043 Uiso 1 1 calc R . . C21 C -0.6356(6) 0.2967(13) -0.5796(4) 0.0462(19) Uani 1 1 d . . . H21A H -0.5790 0.2878 -0.6188 0.055 Uiso 1 1 calc R . . H21B H -0.6522 0.4433 -0.5700 0.055 Uiso 1 1 calc R . . C22 C -0.7441(5) 0.1771(10) -0.6100(4) 0.0341(16) Uani 1 1 d . . . C23 C -0.7911(5) 0.1120(13) -0.5282(4) 0.0421(19) Uani 1 1 d . . . C24 C -0.8879(6) -0.0436(15) -0.5400(4) 0.054(2) Uani 1 1 d . . . H24A H -0.9135 -0.0781 -0.4878 0.081 Uiso 1 1 calc R . . H24B H -0.8619 -0.1687 -0.5652 0.081 Uiso 1 1 calc R . . H24C H -0.9498 0.0168 -0.5746 0.081 Uiso 1 1 calc R . . C25 C -0.8265(6) 0.2918(11) -0.4793(4) 0.0430(18) Uani 1 1 d . . . H25A H -0.8544 0.2410 -0.4298 0.064 Uiso 1 1 calc R . . H25B H -0.8858 0.3688 -0.5106 0.064 Uiso 1 1 calc R . . H25C H -0.7621 0.3824 -0.4659 0.064 Uiso 1 1 calc R . . C26 C -0.8213(6) 0.2825(11) -0.6744(4) 0.0441(18) Uani 1 1 d . . . H26A H -0.7802 0.3118 -0.7210 0.066 Uiso 1 1 calc R . . H26B H -0.8488 0.4116 -0.6532 0.066 Uiso 1 1 calc R . . H26C H -0.8849 0.1923 -0.6907 0.066 Uiso 1 1 calc R . . C27 C -0.7040(6) -0.0287(12) -0.6351(5) 0.0422(18) 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 O1 0.043(3) 0.066(4) 0.038(3) 0.013(3) -0.003(2) -0.017(3) O2 0.047(3) 0.045(3) 0.066(4) 0.009(3) 0.002(3) 0.007(3) O3 0.043(3) 0.028(3) 0.054(3) 0.007(2) -0.007(2) 0.004(3) O4 0.067(4) 0.041(3) 0.029(3) 0.002(2) 0.004(2) 0.000(3) O5 0.049(3) 0.035(3) 0.040(3) 0.004(2) 0.008(2) 0.006(2) O6 0.044(3) 0.034(3) 0.033(3) 0.012(2) 0.008(2) 0.016(2) O7 0.071(4) 0.057(4) 0.034(3) -0.002(3) 0.011(3) -0.009(3) N1 0.039(3) 0.034(3) 0.045(4) 0.013(3) -0.004(3) 0.007(3) C1 0.041(4) 0.026(3) 0.034(4) 0.003(3) 0.002(3) 0.003(3) C2 0.040(4) 0.045(4) 0.026(4) 0.004(3) 0.008(3) 0.008(4) C3 0.058(5) 0.026(4) 0.036(4) 0.008(3) 0.021(4) 0.010(4) C4 0.044(4) 0.025(4) 0.038(4) -0.006(3) 0.002(3) -0.004(3) C5 0.043(4) 0.029(4) 0.028(4) -0.002(3) 0.000(3) 0.002(3) C6 0.051(4) 0.040(4) 0.048(5) 0.007(4) 0.012(4) 0.005(4) C7 0.069(6) 0.047(5) 0.041(5) -0.002(4) 0.011(4) -0.015(4) C8 0.042(4) 0.048(5) 0.039(4) 0.012(4) -0.001(3) 0.014(4) C9 0.043(5) 0.059(5) 0.058(5) 0.007(4) -0.009(4) 0.002(4) C10 0.056(5) 0.046(5) 0.088(7) -0.014(5) 0.025(5) -0.015(4) C11 0.064(5) 0.041(5) 0.048(5) 0.005(4) -0.005(4) -0.017(4) C12 0.036(4) 0.028(4) 0.034(4) 0.001(3) 0.002(3) -0.008(3) C13 0.048(5) 0.045(4) 0.029(4) -0.009(4) -0.009(3) 0.001(4) C14 0.049(5) 0.059(5) 0.053(5) -0.014(4) 0.008(4) -0.007(4) C15 0.053(5) 0.071(6) 0.049(5) 0.005(5) -0.004(4) 0.006(5) C16 0.050(5) 0.041(4) 0.045(4) 0.001(4) -0.014(4) -0.001(4) C17 0.067(5) 0.047(5) 0.030(4) 0.005(4) 0.016(4) 0.007(4) C18 0.034(4) 0.038(4) 0.031(4) 0.007(3) 0.006(3) 0.007(3) C19 0.032(4) 0.037(4) 0.020(3) -0.005(3) 0.007(3) -0.005(3) C20 0.033(4) 0.038(4) 0.035(4) 0.009(3) 0.000(3) 0.013(3) C21 0.036(4) 0.066(5) 0.037(4) 0.016(4) 0.002(3) -0.011(4) C22 0.033(4) 0.032(4) 0.037(4) 0.001(3) 0.002(3) -0.017(3) C23 0.017(3) 0.071(5) 0.038(4) 0.003(4) -0.003(3) -0.003(4) C24 0.039(4) 0.082(6) 0.041(4) 0.007(4) -0.001(3) -0.027(4) C25 0.039(4) 0.026(3) 0.064(5) -0.001(4) 0.008(4) 0.014(4) C26 0.041(4) 0.035(4) 0.053(5) 0.009(4) -0.013(3) 0.005(4) C27 0.044(4) 0.043(4) 0.040(4) 0.012(4) 0.003(3) 0.002(4) _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 1.235(8) . ? O2 C8 1.204(9) . ? O3 C8 1.340(8) . ? O3 C9 1.453(9) . ? O4 C18 1.362(8) . ? O4 C3 1.451(8) . ? O5 C18 1.210(8) . ? O6 C27 1.419(8) . ? O6 C19 1.498(7) . ? O7 C27 1.206(8) . ? N1 C1 1.468(8) . ? N1 C5 1.483(9) . ? N1 H1A 0.8800 . ? C1 C8 1.496(10) . ? C1 C6 1.545(9) . ? C1 C2 1.555(9) . ? C2 C3 1.472(10) . ? C3 C4 1.328(9) . ? C4 C11 1.514(9) . ? C4 C5 1.516(9) . ? C5 C12 1.536(9) . ? C5 H5A 1.0000 . ? C6 C7 1.536(10) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C9 C10 1.511(10) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C17 1.383(9) . ? C12 C13 1.400(9) . ? C13 C14 1.370(10) . ? C13 H13A 0.9500 . ? C14 C15 1.402(10) . ? C14 H14A 0.9500 . ? C15 C16 1.386(11) . ? C15 H15A 0.9500 . ? C16 C17 1.392(10) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C19 1.528(9) . ? C19 C23 1.510(9) . ? C19 C20 1.529(9) . ? C20 C21 1.538(9) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.560(9) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C27 1.495(10) . ? C22 C26 1.516(9) . ? C22 C23 1.586(9) . ? C23 C25 1.511(10) . ? C23 C24 1.539(10) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 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 C8 O3 C9 119.6(6) . . ? C18 O4 C3 113.0(5) . . ? C27 O6 C19 103.1(5) . . ? C1 N1 C5 116.3(5) . . ? C1 N1 H1A 121.8 . . ? C5 N1 H1A 121.8 . . ? N1 C1 C8 108.6(6) . . ? N1 C1 C6 111.6(6) . . ? C8 C1 C6 110.9(6) . . ? N1 C1 C2 109.5(5) . . ? C8 C1 C2 108.5(6) . . ? C6 C1 C2 107.7(5) . . ? O1 C2 C3 122.6(6) . . ? O1 C2 C1 121.9(6) . . ? C3 C2 C1 115.2(6) . . ? C4 C3 O4 118.0(6) . . ? C4 C3 C2 127.0(6) . . ? O4 C3 C2 113.8(6) . . ? C3 C4 C11 124.6(6) . . ? C3 C4 C5 117.2(6) . . ? C11 C4 C5 118.1(6) . . ? N1 C5 C4 113.2(5) . . ? N1 C5 C12 106.8(5) . . ? C4 C5 C12 111.7(5) . . ? N1 C5 H5A 108.3 . . ? C4 C5 H5A 108.3 . . ? C12 C5 H5A 108.3 . . ? C7 C6 C1 111.8(6) . . ? C7 C6 H6A 109.3 . . ? C1 C6 H6A 109.3 . . ? C7 C6 H6B 109.3 . . ? C1 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 O3 122.5(8) . . ? O2 C8 C1 124.0(7) . . ? O3 C8 C1 113.5(6) . . ? O3 C9 C10 110.0(7) . . ? O3 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? O3 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C4 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 118.4(6) . . ? C17 C12 C5 120.7(6) . . ? C13 C12 C5 120.8(6) . . ? C14 C13 C12 120.7(6) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 120.1(7) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C16 C15 C14 120.2(8) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C15 C16 C17 118.7(7) . . ? C15 C16 H16A 120.7 . . ? C17 C16 H16A 120.7 . . ? C12 C17 C16 121.9(7) . . ? C12 C17 H17A 119.0 . . ? C16 C17 H17A 119.0 . . ? O5 C18 O4 124.4(6) . . ? O5 C18 C19 127.5(6) . . ? O4 C18 C19 108.0(6) . . ? O6 C19 C23 103.3(5) . . ? O6 C19 C18 103.7(5) . . ? C23 C19 C18 118.7(5) . . ? O6 C19 C20 107.8(5) . . ? C23 C19 C20 105.1(6) . . ? C18 C19 C20 116.9(5) . . ? C19 C20 C21 101.0(5) . . ? C19 C20 H20A 111.6 . . ? C21 C20 H20A 111.6 . . ? C19 C20 H20B 111.6 . . ? C21 C20 H20B 111.6 . . ? H20A C20 H20B 109.4 . . ? C20 C21 C22 104.0(5) . . ? C20 C21 H21A 111.0 . . ? C22 C21 H21A 111.0 . . ? C20 C21 H21B 111.0 . . ? C22 C21 H21B 111.0 . . ? H21A C21 H21B 109.0 . . ? C27 C22 C26 113.4(6) . . ? C27 C22 C21 104.8(6) . . ? C26 C22 C21 116.2(6) . . ? C27 C22 C23 98.8(6) . . ? C26 C22 C23 119.4(6) . . ? C21 C22 C23 101.8(5) . . ? C19 C23 C25 115.6(6) . . ? C19 C23 C24 113.3(7) . . ? C25 C23 C24 109.3(6) . . ? C19 C23 C22 91.0(5) . . ? C25 C23 C22 113.7(6) . . ? C24 C23 C22 113.0(6) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O7 C27 O6 117.7(7) . . ? O7 C27 C22 134.7(7) . . ? O6 C27 C22 107.5(6) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 32.72 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.349 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.072