# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jie Wu' _publ_contact_author_address ; ; _publ_contact_author_email 'jie wu@fudan.edu.cn' loop_ _publ_author_name 'Shaoyu Li' 'Jie Wu' # Attachment '- a20221a.cif' data_a20221a _database_code_depnum_ccdc_archive 'CCDC 887776' #TrackingRef '- a20221a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H28 N2 O5 S' _chemical_formula_weight 468.55 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 31.177(14) _cell_length_b 9.345(4) _cell_length_c 8.033(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2340.6(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 2.852 _cell_measurement_theta_max 26.236 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9739 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 10794 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4895 _reflns_number_gt 4257 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0623P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.10(8) _refine_ls_number_reflns 4895 _refine_ls_number_parameters 300 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 S1 S 0.523054(16) 0.64676(6) 0.66915(8) 0.04329(15) Uani 1 1 d . . . N1 N 0.56072(5) 0.52273(18) 0.6763(3) 0.0375(4) Uani 1 1 d . . . N2 N 0.59784(7) 0.3641(2) 0.8314(3) 0.0483(5) Uani 1 1 d . . . O1 O 0.48551(5) 0.5728(2) 0.7140(3) 0.0636(6) Uani 1 1 d . . . O2 O 0.52614(6) 0.7115(2) 0.5115(2) 0.0583(5) Uani 1 1 d . . . O3 O 0.60080(6) 0.2201(2) 0.5191(3) 0.0669(6) Uani 1 1 d . . . O4 O 0.67048(6) 0.23504(17) 0.5742(2) 0.0504(4) Uani 1 1 d . . . O5 O 0.61988(5) 0.66383(15) 0.6877(2) 0.0403(4) Uani 1 1 d . . . C1 C 0.56337(8) 0.4280(3) 0.8102(3) 0.0454(6) Uani 1 1 d . . . H1 H 0.5402 0.4133 0.8809 0.054 Uiso 1 1 calc R . . C2 C 0.62583(7) 0.4076(2) 0.6942(3) 0.0387(5) Uani 1 1 d . . . H2 H 0.6540 0.4351 0.7377 0.046 Uiso 1 1 calc R . . C3 C 0.60429(7) 0.5378(2) 0.6108(3) 0.0363(5) Uani 1 1 d . . . C4 C 0.60514(7) 0.5493(3) 0.4235(3) 0.0427(6) Uani 1 1 d . . . H4A H 0.5833 0.4866 0.3778 0.051 Uiso 1 1 calc R . . H4B H 0.5979 0.6466 0.3922 0.051 Uiso 1 1 calc R . . C5 C 0.64745(7) 0.5116(3) 0.3477(3) 0.0409(5) Uani 1 1 d . . . C6 C 0.64825(8) 0.4200(3) 0.2139(3) 0.0485(6) Uani 1 1 d . . . H6 H 0.6226 0.3832 0.1729 0.058 Uiso 1 1 calc R . . C7 C 0.68675(10) 0.3816(3) 0.1391(3) 0.0583(7) Uani 1 1 d . . . H7 H 0.6870 0.3194 0.0487 0.070 Uiso 1 1 calc R . . C8 C 0.72390(9) 0.4359(3) 0.1994(4) 0.0599(7) Uani 1 1 d . . . H8 H 0.7499 0.4096 0.1512 0.072 Uiso 1 1 calc R . . C9 C 0.72354(8) 0.5284(3) 0.3300(3) 0.0517(6) Uani 1 1 d . . . H9 H 0.7494 0.5665 0.3673 0.062 Uiso 1 1 calc R . . C10 C 0.68564(7) 0.5680(3) 0.4095(3) 0.0427(5) Uani 1 1 d . . . C11 C 0.68856(7) 0.6658(3) 0.5488(3) 0.0458(6) Uani 1 1 d . . . H11 H 0.7154 0.7082 0.5590 0.055 Uiso 1 1 calc R . . C12 C 0.66109(7) 0.7078(2) 0.6650(3) 0.0403(5) Uani 1 1 d . . . C13 C 0.67162(9) 0.8137(3) 0.7979(4) 0.0496(6) Uani 1 1 d . . . H13A H 0.6549 0.8997 0.7792 0.060 Uiso 1 1 calc R . . H13B H 0.7017 0.8395 0.7883 0.060 Uiso 1 1 calc R . . C14 C 0.66333(9) 0.7615(3) 0.9725(3) 0.0535(7) Uani 1 1 d . . . H14A H 0.6332 0.7377 0.9835 0.064 Uiso 1 1 calc R . . H14B H 0.6797 0.6747 0.9912 0.064 Uiso 1 1 calc R . . C15 C 0.67497(12) 0.8691(3) 1.1035(4) 0.0725(9) Uani 1 1 d . . . H15A H 0.7055 0.8817 1.1053 0.109 Uiso 1 1 calc R . . H15B H 0.6655 0.8356 1.2103 0.109 Uiso 1 1 calc R . . H15C H 0.6614 0.9588 1.0788 0.109 Uiso 1 1 calc R . . C16 C 0.63024(8) 0.2778(3) 0.5836(3) 0.0431(5) Uani 1 1 d . . . C17 C 0.67794(10) 0.1115(3) 0.4690(4) 0.0603(8) Uani 1 1 d . . . H17A H 0.6676 0.1297 0.3571 0.072 Uiso 1 1 calc R . . H17B H 0.6631 0.0285 0.5130 0.072 Uiso 1 1 calc R . . C18 C 0.72472(12) 0.0863(4) 0.4674(5) 0.0840(11) Uani 1 1 d . . . H18A H 0.7389 0.1660 0.4158 0.126 Uiso 1 1 calc R . . H18B H 0.7308 0.0006 0.4059 0.126 Uiso 1 1 calc R . . H18C H 0.7349 0.0758 0.5796 0.126 Uiso 1 1 calc R . . C19 C 0.53453(7) 0.7728(2) 0.8222(3) 0.0371(5) Uani 1 1 d . . . C20 C 0.55223(9) 0.9022(3) 0.7797(4) 0.0521(6) Uani 1 1 d . . . H20 H 0.5579 0.9241 0.6690 0.063 Uiso 1 1 calc R . . C21 C 0.56121(10) 0.9973(3) 0.9016(5) 0.0622(8) Uani 1 1 d . . . H21 H 0.5724 1.0862 0.8729 0.075 Uiso 1 1 calc R . . C22 C 0.55429(9) 0.9667(3) 1.0661(4) 0.0623(8) Uani 1 1 d . . . C23 C 0.53607(12) 0.8374(3) 1.1056(4) 0.0650(8) Uani 1 1 d . . . H23 H 0.5306 0.8155 1.2165 0.078 Uiso 1 1 calc R . . C24 C 0.52598(9) 0.7413(3) 0.9859(4) 0.0550(7) Uani 1 1 d . . . H24 H 0.5133 0.6545 1.0142 0.066 Uiso 1 1 calc R . . C25 C 0.56641(12) 1.0691(4) 1.2014(6) 0.1022(15) Uani 1 1 d . . . H25D H 0.5786 1.1539 1.1531 0.153 Uiso 1 1 calc R . . H25A H 0.5871 1.0250 1.2736 0.153 Uiso 1 1 calc R . . H25B H 0.5413 1.0942 1.2644 0.153 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 S1 0.0314(2) 0.0536(3) 0.0449(3) -0.0120(3) -0.0034(3) -0.0032(2) N1 0.0315(9) 0.0437(10) 0.0372(10) -0.0041(9) 0.0023(9) -0.0070(7) N2 0.0620(14) 0.0465(12) 0.0365(11) 0.0033(9) 0.0073(10) -0.0045(10) O1 0.0325(8) 0.0704(12) 0.0879(15) -0.0301(12) 0.0034(9) -0.0111(8) O2 0.0550(11) 0.0795(14) 0.0405(10) -0.0057(10) -0.0105(9) 0.0142(9) O3 0.0570(12) 0.0666(12) 0.0769(14) -0.0290(12) -0.0036(10) -0.0147(10) O4 0.0536(10) 0.0479(10) 0.0496(10) -0.0068(9) -0.0013(8) 0.0078(8) O5 0.0345(7) 0.0395(8) 0.0470(9) -0.0051(8) 0.0014(8) -0.0089(6) C1 0.0490(14) 0.0446(13) 0.0426(14) -0.0027(11) 0.0130(12) -0.0105(11) C2 0.0375(11) 0.0424(11) 0.0363(12) -0.0027(10) -0.0017(10) -0.0038(9) C3 0.0299(11) 0.0404(12) 0.0388(12) -0.0018(9) 0.0000(8) -0.0063(9) C4 0.0327(12) 0.0619(16) 0.0336(12) -0.0001(11) -0.0044(9) -0.0052(11) C5 0.0398(12) 0.0516(14) 0.0312(11) 0.0076(10) 0.0028(10) -0.0027(10) C6 0.0494(14) 0.0625(15) 0.0336(12) 0.0029(11) -0.0023(10) -0.0064(12) C7 0.0670(18) 0.0707(18) 0.0371(16) -0.0012(13) 0.0115(12) 0.0033(14) C8 0.0514(15) 0.0793(18) 0.0490(17) 0.0100(15) 0.0158(14) 0.0077(13) C9 0.0388(13) 0.0724(18) 0.0438(14) 0.0100(13) 0.0055(11) -0.0017(12) C10 0.0394(12) 0.0545(14) 0.0343(12) 0.0085(11) 0.0031(10) -0.0053(11) C11 0.0341(12) 0.0575(15) 0.0457(14) 0.0045(12) -0.0001(10) -0.0147(10) C12 0.0360(11) 0.0430(11) 0.0417(12) 0.0076(12) -0.0051(11) -0.0125(9) C13 0.0488(14) 0.0462(14) 0.0537(15) -0.0034(12) -0.0013(12) -0.0188(11) C14 0.0542(15) 0.0569(16) 0.0493(15) -0.0050(13) -0.0017(12) -0.0075(13) C15 0.080(2) 0.080(2) 0.0578(18) -0.0133(17) -0.0078(15) -0.0166(17) C16 0.0464(13) 0.0449(14) 0.0379(12) -0.0023(11) -0.0005(11) -0.0040(11) C17 0.082(2) 0.0473(16) 0.0519(16) -0.0094(13) 0.0018(14) 0.0127(14) C18 0.087(2) 0.087(2) 0.078(2) -0.024(2) -0.0018(19) 0.039(2) C19 0.0362(11) 0.0366(12) 0.0386(12) -0.0056(10) -0.0011(10) -0.0017(9) C20 0.0542(15) 0.0433(14) 0.0588(16) 0.0058(12) 0.0025(12) -0.0026(12) C21 0.0557(18) 0.0356(14) 0.095(3) -0.0082(15) -0.0070(16) -0.0040(12) C22 0.0518(15) 0.0567(17) 0.078(2) -0.0299(16) -0.0158(15) 0.0107(13) C23 0.087(2) 0.0655(19) 0.0426(15) -0.0081(13) 0.0003(15) 0.0118(17) C24 0.0746(19) 0.0440(14) 0.0463(14) -0.0013(12) 0.0048(13) -0.0073(13) C25 0.077(2) 0.102(3) 0.127(4) -0.079(3) -0.021(2) 0.018(2) _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 S1 O1 1.4061(19) . ? S1 O2 1.406(2) . ? S1 N1 1.6510(19) . ? S1 C19 1.740(2) . ? N1 C1 1.395(3) . ? N1 C3 1.464(3) . ? N2 C1 1.241(3) . ? N2 C2 1.463(3) . ? O3 C16 1.184(3) . ? O4 C16 1.319(3) . ? O4 C17 1.449(3) . ? O5 C12 1.361(3) . ? O5 C3 1.417(3) . ? C1 H1 0.9300 . ? C2 C16 1.510(3) . ? C2 C3 1.543(3) . ? C2 H2 0.9800 . ? C3 C4 1.508(3) . ? C4 C5 1.495(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.374(3) . ? C5 C10 1.393(3) . ? C6 C7 1.390(4) . ? C6 H6 0.9300 . ? C7 C8 1.354(4) . ? C7 H7 0.9300 . ? C8 C9 1.359(4) . ? C8 H8 0.9300 . ? C9 C10 1.393(3) . ? C9 H9 0.9300 . ? C10 C11 1.448(4) . ? C11 C12 1.326(4) . ? C11 H11 0.9300 . ? C12 C13 1.493(3) . ? C13 C14 1.508(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.500(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C17 C18 1.477(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.372(3) . ? C19 C24 1.374(4) . ? C20 C21 1.352(4) . ? C20 H20 0.9300 . ? C21 C22 1.369(5) . ? C21 H21 0.9300 . ? C22 C23 1.372(4) . ? C22 C25 1.497(4) . ? C23 C24 1.353(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25D 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? 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 O1 S1 O2 119.92(12) . . ? O1 S1 N1 103.77(11) . . ? O2 S1 N1 106.54(11) . . ? O1 S1 C19 108.84(12) . . ? O2 S1 C19 109.33(12) . . ? N1 S1 C19 107.71(11) . . ? C1 N1 C3 106.47(17) . . ? C1 N1 S1 120.96(16) . . ? C3 N1 S1 125.46(15) . . ? C1 N2 C2 106.2(2) . . ? C16 O4 C17 115.3(2) . . ? C12 O5 C3 121.09(18) . . ? N2 C1 N1 117.5(2) . . ? N2 C1 H1 121.2 . . ? N1 C1 H1 121.2 . . ? N2 C2 C16 105.89(18) . . ? N2 C2 C3 106.66(18) . . ? C16 C2 C3 114.7(2) . . ? N2 C2 H2 109.8 . . ? C16 C2 H2 109.8 . . ? C3 C2 H2 109.8 . . ? O5 C3 N1 103.96(17) . . ? O5 C3 C4 111.7(2) . . ? N1 C3 C4 112.47(18) . . ? O5 C3 C2 108.46(17) . . ? N1 C3 C2 99.90(17) . . ? C4 C3 C2 118.8(2) . . ? C5 C4 C3 113.9(2) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C10 119.9(2) . . ? C6 C5 C4 118.8(2) . . ? C10 C5 C4 121.3(2) . . ? C5 C6 C7 121.0(2) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 119.1(3) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 120.5(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C10 122.0(3) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C9 C10 C5 117.5(2) . . ? C9 C10 C11 117.9(2) . . ? C5 C10 C11 124.6(2) . . ? C12 C11 C10 133.6(2) . . ? C12 C11 H11 113.2 . . ? C10 C11 H11 113.2 . . ? C11 C12 O5 127.9(2) . . ? C11 C12 C13 123.9(2) . . ? O5 C12 C13 108.2(2) . . ? C12 C13 C14 114.4(2) . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 113.2(2) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 O4 125.1(2) . . ? O3 C16 C2 123.6(2) . . ? O4 C16 C2 111.3(2) . . ? O4 C17 C18 106.9(3) . . ? O4 C17 H17A 110.3 . . ? C18 C17 H17A 110.3 . . ? O4 C17 H17B 110.3 . . ? C18 C17 H17B 110.3 . . ? H17A C17 H17B 108.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 120.3(2) . . ? C20 C19 S1 120.2(2) . . ? C24 C19 S1 119.43(19) . . ? C21 C20 C19 118.9(3) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? C20 C21 C22 122.0(3) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C21 C22 C23 118.2(3) . . ? C21 C22 C25 121.9(3) . . ? C23 C22 C25 120.0(3) . . ? C24 C23 C22 121.1(3) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C19 119.5(3) . . ? C23 C24 H24 120.2 . . ? C19 C24 H24 120.2 . . ? C22 C25 H25D 109.5 . . ? C22 C25 H25A 109.5 . . ? H25D C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25D C25 H25B 109.5 . . ? H25A C25 H25B 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 O1 S1 N1 C1 -45.63(19) . . . . ? O2 S1 N1 C1 -173.11(18) . . . . ? C19 S1 N1 C1 69.67(19) . . . . ? O1 S1 N1 C3 167.96(19) . . . . ? O2 S1 N1 C3 40.5(2) . . . . ? C19 S1 N1 C3 -76.7(2) . . . . ? C2 N2 C1 N1 -2.7(3) . . . . ? C3 N1 C1 N2 -9.4(3) . . . . ? S1 N1 C1 N2 -161.40(19) . . . . ? C1 N2 C2 C16 -109.5(2) . . . . ? C1 N2 C2 C3 13.1(3) . . . . ? C12 O5 C3 N1 175.63(19) . . . . ? C12 O5 C3 C4 -62.9(3) . . . . ? C12 O5 C3 C2 70.0(2) . . . . ? C1 N1 C3 O5 -96.3(2) . . . . ? S1 N1 C3 O5 54.0(2) . . . . ? C1 N1 C3 C4 142.7(2) . . . . ? S1 N1 C3 C4 -67.0(3) . . . . ? C1 N1 C3 C2 15.7(2) . . . . ? S1 N1 C3 C2 166.02(16) . . . . ? N2 C2 C3 O5 91.0(2) . . . . ? C16 C2 C3 O5 -152.09(19) . . . . ? N2 C2 C3 N1 -17.4(2) . . . . ? C16 C2 C3 N1 99.5(2) . . . . ? N2 C2 C3 C4 -140.0(2) . . . . ? C16 C2 C3 C4 -23.2(3) . . . . ? O5 C3 C4 C5 84.7(3) . . . . ? N1 C3 C4 C5 -158.85(19) . . . . ? C2 C3 C4 C5 -42.7(3) . . . . ? C3 C4 C5 C6 132.4(2) . . . . ? C3 C4 C5 C10 -47.9(3) . . . . ? C10 C5 C6 C7 0.3(4) . . . . ? C4 C5 C6 C7 -180.0(2) . . . . ? C5 C6 C7 C8 -0.1(4) . . . . ? C6 C7 C8 C9 -1.0(4) . . . . ? C7 C8 C9 C10 1.8(4) . . . . ? C8 C9 C10 C5 -1.6(4) . . . . ? C8 C9 C10 C11 179.2(2) . . . . ? C6 C5 C10 C9 0.5(3) . . . . ? C4 C5 C10 C9 -179.2(2) . . . . ? C6 C5 C10 C11 179.6(2) . . . . ? C4 C5 C10 C11 -0.1(4) . . . . ? C9 C10 C11 C12 -168.1(3) . . . . ? C5 C10 C11 C12 12.7(5) . . . . ? C10 C11 C12 O5 1.8(5) . . . . ? C10 C11 C12 C13 -179.2(3) . . . . ? C3 O5 C12 C11 16.1(4) . . . . ? C3 O5 C12 C13 -163.1(2) . . . . ? C11 C12 C13 C14 -125.5(3) . . . . ? O5 C12 C13 C14 53.6(3) . . . . ? C12 C13 C14 C15 178.9(3) . . . . ? C17 O4 C16 O3 3.0(4) . . . . ? C17 O4 C16 C2 -179.4(2) . . . . ? N2 C2 C16 O3 59.2(3) . . . . ? C3 C2 C16 O3 -58.1(3) . . . . ? N2 C2 C16 O4 -118.5(2) . . . . ? C3 C2 C16 O4 124.2(2) . . . . ? C16 O4 C17 C18 176.8(3) . . . . ? O1 S1 C19 C20 -144.9(2) . . . . ? O2 S1 C19 C20 -12.2(2) . . . . ? N1 S1 C19 C20 103.2(2) . . . . ? O1 S1 C19 C24 35.5(2) . . . . ? O2 S1 C19 C24 168.2(2) . . . . ? N1 S1 C19 C24 -76.4(2) . . . . ? C24 C19 C20 C21 0.3(4) . . . . ? S1 C19 C20 C21 -179.3(2) . . . . ? C19 C20 C21 C22 1.9(5) . . . . ? C20 C21 C22 C23 -2.7(5) . . . . ? C20 C21 C22 C25 176.7(3) . . . . ? C21 C22 C23 C24 1.3(5) . . . . ? C25 C22 C23 C24 -178.0(3) . . . . ? C22 C23 C24 C19 0.7(5) . . . . ? C20 C19 C24 C23 -1.6(4) . . . . ? S1 C19 C24 C23 178.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.168 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.040 # Attachment '- a20229a.cif' data_a20229a _database_code_depnum_ccdc_archive 'CCDC 887777' #TrackingRef '- a20229a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N O3 S' _chemical_formula_weight 355.44 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.000(16) _cell_length_b 7.953(8) _cell_length_c 16.368(17) _cell_angle_alpha 90.00 _cell_angle_beta 116.951(12) _cell_angle_gamma 90.00 _cell_volume 1857(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1003 _cell_measurement_theta_min 2.406 _cell_measurement_theta_max 26.274 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9358 _exptl_absorpt_correction_T_max 0.9535 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 7386 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3257 _reflns_number_gt 2557 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1173P)^2^+0.1646P] 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 SHELXL _refine_ls_extinction_coef 0.111(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3257 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0755 _refine_ls_wR_factor_ref 0.1899 _refine_ls_wR_factor_gt 0.1763 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 N1 N -0.05549(15) 0.4458(3) 0.08581(13) 0.0583(6) Uani 1 1 d . . . O1 O -0.19355(15) 0.3267(3) 0.10312(16) 0.0842(7) Uani 1 1 d . . . O2 O -0.21221(15) 0.5558(3) -0.00434(13) 0.0897(7) Uani 1 1 d . . . O3 O 0.00778(11) 0.3605(2) 0.23522(10) 0.0580(5) Uani 1 1 d . . . S1 S -0.15852(4) 0.47857(9) 0.08298(4) 0.0630(3) Uani 1 1 d . . . C1 C 0.01400(17) 0.3875(3) 0.15747(15) 0.0498(6) Uani 1 1 d . . . C2 C 0.10366(18) 0.3471(3) 0.15508(18) 0.0585(6) Uani 1 1 d . . . H2A H 0.1556 0.3978 0.2073 0.070 Uiso 1 1 calc R . . H2B H 0.1028 0.3926 0.0997 0.070 Uiso 1 1 calc R . . C3 C 0.11638(17) 0.1602(3) 0.15740(19) 0.0605(7) Uani 1 1 d . . . C4 C 0.1164(2) 0.0767(5) 0.0834(3) 0.0930(10) Uani 1 1 d . . . H4 H 0.1066 0.1354 0.0306 0.112 Uiso 1 1 calc R . . C5 C 0.1314(3) -0.0953(7) 0.0884(4) 0.1252(18) Uani 1 1 d . . . H5 H 0.1313 -0.1516 0.0386 0.150 Uiso 1 1 calc R . . C6 C 0.1460(3) -0.1830(5) 0.1647(5) 0.126(2) Uani 1 1 d . . . H6 H 0.1562 -0.2984 0.1668 0.151 Uiso 1 1 calc R . . C7 C 0.1461(2) -0.1023(4) 0.2397(3) 0.0988(13) Uani 1 1 d . . . H7 H 0.1569 -0.1633 0.2921 0.119 Uiso 1 1 calc R . . C8 C 0.12962(17) 0.0720(3) 0.2368(2) 0.0656(7) Uani 1 1 d . . . C9 C 0.12968(19) 0.1584(4) 0.3148(2) 0.0713(8) Uani 1 1 d . . . H9 H 0.1703 0.1151 0.3720 0.086 Uiso 1 1 calc R . . C10 C 0.08002(17) 0.2900(4) 0.31586(17) 0.0623(7) Uani 1 1 d . . . C11 C 0.0841(2) 0.3773(4) 0.39759(18) 0.0759(8) Uani 1 1 d . . . H11A H 0.1268 0.3168 0.4521 0.091 Uiso 1 1 calc R . . H11B H 0.0225 0.3739 0.3952 0.091 Uiso 1 1 calc R . . C12 C 0.1158(2) 0.5589(5) 0.4059(2) 0.0858(10) Uani 1 1 d . . . H12A H 0.0733 0.6198 0.3515 0.103 Uiso 1 1 calc R . . H12B H 0.1777 0.5628 0.4090 0.103 Uiso 1 1 calc R . . C13 C 0.1188(3) 0.6454(7) 0.4902(3) 0.1222(16) Uani 1 1 d . . . H13A H 0.0571 0.6462 0.4863 0.183 Uiso 1 1 calc R . . H13B H 0.1404 0.7589 0.4932 0.183 Uiso 1 1 calc R . . H13C H 0.1608 0.5857 0.5443 0.183 Uiso 1 1 calc R . . C14 C -0.14118(16) 0.6298(3) 0.16797(16) 0.0543(6) Uani 1 1 d . . . C15 C -0.1174(3) 0.7911(4) 0.1566(2) 0.0789(8) Uani 1 1 d . . . H15 H -0.1103 0.8190 0.1050 0.095 Uiso 1 1 calc R . . C16 C -0.1041(2) 0.9116(4) 0.2222(2) 0.0849(9) Uani 1 1 d . . . H16 H -0.0863 1.0197 0.2149 0.102 Uiso 1 1 calc R . . C17 C -0.11661(19) 0.8749(4) 0.2979(2) 0.0724(8) Uani 1 1 d . . . C18 C -0.1420(2) 0.7146(4) 0.3069(2) 0.0785(9) Uani 1 1 d . . . H18 H -0.1513 0.6881 0.3575 0.094 Uiso 1 1 calc R . . C19 C -0.1543(2) 0.5905(4) 0.24336(19) 0.0694(7) Uani 1 1 d . . . H19 H -0.1711 0.4821 0.2513 0.083 Uiso 1 1 calc R . . C20 C -0.1003(3) 1.0087(6) 0.3692(3) 0.1076(13) Uani 1 1 d . . . H20A H -0.0349 1.0368 0.4000 0.161 Uiso 1 1 calc R . . H20B H -0.1197 0.9671 0.4131 0.161 Uiso 1 1 calc R . . H20C H -0.1361 1.1072 0.3399 0.161 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 N1 0.0696(13) 0.0584(13) 0.0450(11) -0.0009(9) 0.0244(10) 0.0116(10) O1 0.0785(13) 0.0699(13) 0.1026(16) -0.0269(11) 0.0395(12) -0.0119(10) O2 0.0814(14) 0.1054(17) 0.0490(11) -0.0178(10) 0.0002(9) 0.0251(12) O3 0.0597(10) 0.0693(11) 0.0461(9) 0.0037(7) 0.0251(8) 0.0087(8) S1 0.0587(5) 0.0651(5) 0.0525(5) -0.0177(3) 0.0142(3) 0.0054(3) C1 0.0629(14) 0.0408(13) 0.0474(13) -0.0040(9) 0.0264(11) 0.0019(9) C2 0.0676(15) 0.0520(14) 0.0648(15) 0.0049(12) 0.0379(13) 0.0066(11) C3 0.0511(13) 0.0524(15) 0.0757(17) -0.0057(13) 0.0268(12) 0.0050(10) C4 0.089(2) 0.092(2) 0.099(2) -0.030(2) 0.0434(19) 0.0174(18) C5 0.090(3) 0.103(4) 0.164(4) -0.069(3) 0.041(3) 0.011(2) C6 0.075(2) 0.050(2) 0.237(6) -0.031(3) 0.057(3) 0.0005(16) C7 0.069(2) 0.0530(18) 0.170(4) 0.018(2) 0.051(2) 0.0088(14) C8 0.0490(13) 0.0512(14) 0.092(2) 0.0094(14) 0.0276(13) 0.0034(11) C9 0.0612(16) 0.0761(19) 0.0713(18) 0.0244(15) 0.0252(13) 0.0069(13) C10 0.0595(14) 0.0731(17) 0.0489(14) 0.0095(12) 0.0198(11) -0.0009(13) C11 0.0746(18) 0.104(2) 0.0493(15) 0.0048(14) 0.0284(13) -0.0046(15) C12 0.083(2) 0.108(3) 0.075(2) -0.0194(18) 0.0429(17) -0.0256(19) C13 0.124(3) 0.158(4) 0.103(3) -0.063(3) 0.067(3) -0.055(3) C14 0.0497(12) 0.0576(15) 0.0492(13) -0.0104(11) 0.0167(10) 0.0027(10) C15 0.110(2) 0.0656(19) 0.0677(18) -0.0100(15) 0.0464(16) -0.0101(16) C16 0.108(3) 0.0597(18) 0.091(2) -0.0212(16) 0.0489(19) -0.0168(16) C17 0.0574(15) 0.082(2) 0.0731(18) -0.0306(16) 0.0252(13) -0.0016(13) C18 0.090(2) 0.091(2) 0.0665(17) -0.0122(16) 0.0463(16) 0.0012(17) C19 0.0824(19) 0.0633(17) 0.0725(17) -0.0088(14) 0.0439(15) -0.0042(13) C20 0.090(2) 0.121(3) 0.101(3) -0.065(2) 0.034(2) -0.011(2) _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 N1 C1 1.283(3) . ? N1 S1 1.649(3) . ? O1 S1 1.431(2) . ? O2 S1 1.430(2) . ? O3 C1 1.338(3) . ? O3 C10 1.418(3) . ? S1 C14 1.763(3) . ? C1 C2 1.488(4) . ? C2 C3 1.498(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.383(4) . ? C3 C8 1.405(4) . ? C4 C5 1.384(6) . ? C4 H4 0.9300 . ? C5 C6 1.355(7) . ? C5 H5 0.9300 . ? C6 C7 1.385(7) . ? C6 H6 0.9300 . ? C7 C8 1.408(4) . ? C7 H7 0.9300 . ? C8 C9 1.450(4) . ? C9 C10 1.319(4) . ? C9 H9 0.9300 . ? C10 C11 1.482(4) . ? C11 C12 1.516(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.523(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.374(4) . ? C14 C19 1.378(4) . ? C15 C16 1.381(4) . ? C15 H15 0.9300 . ? C16 C17 1.374(5) . ? C16 H16 0.9300 . ? C17 C18 1.366(5) . ? C17 C20 1.512(4) . ? C18 C19 1.382(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 C1 N1 S1 121.60(18) . . ? C1 O3 C10 124.6(2) . . ? O2 S1 O1 118.18(15) . . ? O2 S1 N1 103.63(14) . . ? O1 S1 N1 110.56(13) . . ? O2 S1 C14 107.69(14) . . ? O1 S1 C14 109.39(14) . . ? N1 S1 C14 106.72(11) . . ? N1 C1 O3 121.4(2) . . ? N1 C1 C2 120.0(2) . . ? O3 C1 C2 118.6(2) . . ? C1 C2 C3 109.6(2) . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C8 120.7(3) . . ? C4 C3 C2 120.6(3) . . ? C8 C3 C2 118.7(2) . . ? C3 C4 C5 119.4(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 121.1(4) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.6(4) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C8 120.0(4) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C3 C8 C7 118.1(3) . . ? C3 C8 C9 121.2(2) . . ? C7 C8 C9 120.7(3) . . ? C10 C9 C8 128.9(2) . . ? C10 C9 H9 115.6 . . ? C8 C9 H9 115.6 . . ? C9 C10 O3 122.9(2) . . ? C9 C10 C11 127.1(3) . . ? O3 C10 C11 109.8(2) . . ? C10 C11 C12 113.8(2) . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 112.6(3) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 119.8(2) . . ? C15 C14 S1 119.0(2) . . ? C19 C14 S1 121.2(2) . . ? C14 C15 C16 119.8(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 121.3(3) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C16 117.9(3) . . ? C18 C17 C20 122.0(3) . . ? C16 C17 C20 120.2(3) . . ? C17 C18 C19 122.2(3) . . ? C17 C18 H18 118.9 . . ? C19 C18 H18 118.9 . . ? C14 C19 C18 119.0(3) . . ? C14 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.347 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.122