# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Wang, Chun-Jiang' _publ_contact_author_email cjwang@whu.edu.cn _publ_section_title ; Organocatalytic Asymmetric Michael Addition of \^I+--Aryl Cyclopentanones to Nitroolefins for Construction of Adjacent Quaternary and Tertiary Stereocenters ; loop_ _publ_author_name 'Chun-Jiang Wang' 'Xiu-Qin Dong' 'Huai-Long Teng' 'Min-Chao Tong' ; He Huang ; 'Hai-Yan Tao' # Attachment '91216dxq-0m.cif' data_91216dxq_0m _database_code_depnum_ccdc_archive 'CCDC 768128' #TrackingRef '91216dxq-0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_absolute_configuration 7S,8S _chemical_formula_sum 'C19 H18 Br N O3' _chemical_formula_weight 388.25 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthohombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.367(4) _cell_length_b 13.132(6) _cell_length_c 16.078(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1766.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 2.343 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6148 _exptl_absorpt_correction_T_max 0.6515 _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 ? _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 10081 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3435 _reflns_number_gt 2914 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0296P)^2^+0.6081P] 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 0.0010(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.011(10) _refine_ls_number_reflns 3435 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 Br1 Br 0.03099(6) 0.28881(3) -0.02365(2) 0.08664(19) Uani 1 1 d . . . C1 C 0.1433(4) 0.3173(2) 0.07625(17) 0.0508(7) Uani 1 1 d . . . C2 C 0.2087(4) 0.4122(2) 0.0887(2) 0.0588(8) Uani 1 1 d . . . H2 H 0.2000 0.4624 0.0482 0.071 Uiso 1 1 calc R . . C3 C 0.2874(4) 0.4314(2) 0.16248(19) 0.0536(8) Uani 1 1 d . . . H3 H 0.3334 0.4950 0.1707 0.064 Uiso 1 1 calc R . . C4 C 0.3000(3) 0.3594(2) 0.22418(17) 0.0396(6) Uani 1 1 d . . . C5 C 0.2324(4) 0.2645(2) 0.20890(17) 0.0453(7) Uani 1 1 d . . . H5 H 0.2398 0.2141 0.2494 0.054 Uiso 1 1 calc R . . C6 C 0.1547(4) 0.2431(2) 0.13530(18) 0.0493(7) Uani 1 1 d . . . H6 H 0.1108 0.1791 0.1261 0.059 Uiso 1 1 calc R . . C7 C 0.3764(3) 0.3797(2) 0.30814(18) 0.0419(6) Uani 1 1 d . . . H7 H 0.3298 0.3306 0.3471 0.050 Uiso 1 1 calc R . . C8 C 0.5596(3) 0.3659(2) 0.31285(18) 0.0428(6) Uani 1 1 d . . . C9 C 0.6556(4) 0.4328(2) 0.2531(2) 0.0549(8) Uani 1 1 d . . . H9A H 0.5997 0.4405 0.2007 0.066 Uiso 1 1 calc R . . H9B H 0.6732 0.4997 0.2769 0.066 Uiso 1 1 calc R . . C10 C 0.8129(4) 0.3779(3) 0.2405(3) 0.0716(10) Uani 1 1 d . . . H10A H 0.8858 0.3913 0.2861 0.086 Uiso 1 1 calc R . . H10B H 0.8631 0.3985 0.1888 0.086 Uiso 1 1 calc R . . C11 C 0.7653(5) 0.2663(3) 0.2380(3) 0.0740(10) Uani 1 1 d . . . H11A H 0.7519 0.2438 0.1809 0.089 Uiso 1 1 calc R . . H11B H 0.8467 0.2246 0.2641 0.089 Uiso 1 1 calc R . . C12 C 0.6114(4) 0.2581(2) 0.28417(19) 0.0508(7) Uani 1 1 d . . . C13 C 0.6127(4) 0.3748(2) 0.40414(19) 0.0493(7) Uani 1 1 d . . . C14 C 0.7111(5) 0.4514(3) 0.4326(2) 0.0669(9) Uani 1 1 d . . . H14 H 0.7551 0.4971 0.3948 0.080 Uiso 1 1 calc R . . C15 C 0.7457(6) 0.4614(4) 0.5160(3) 0.0910(13) Uani 1 1 d . . . H15 H 0.8118 0.5140 0.5337 0.109 Uiso 1 1 calc R . . C16 C 0.6846(7) 0.3957(4) 0.5726(3) 0.0996(16) Uani 1 1 d . . . H16 H 0.7066 0.4039 0.6289 0.120 Uiso 1 1 calc R . . C17 C 0.5910(7) 0.3176(4) 0.5462(3) 0.0923(14) Uani 1 1 d . . . H17 H 0.5510 0.2711 0.5846 0.111 Uiso 1 1 calc R . . C18 C 0.5546(5) 0.3067(3) 0.4627(2) 0.0694(9) Uani 1 1 d . . . H18 H 0.4902 0.2529 0.4457 0.083 Uiso 1 1 calc R . . C19 C 0.3357(4) 0.4855(2) 0.3414(2) 0.0491(7) Uani 1 1 d . . . H19A H 0.3972 0.4988 0.3914 0.059 Uiso 1 1 calc R . . H19B H 0.3640 0.5365 0.3003 0.059 Uiso 1 1 calc R . . N1 N 0.1638(4) 0.4925(2) 0.3603(2) 0.0655(8) Uani 1 1 d . . . O1 O 0.5378(3) 0.18117(15) 0.29601(16) 0.0653(6) Uani 1 1 d . . . O2 O 0.1114(4) 0.4411(4) 0.4147(3) 0.1314(15) Uani 1 1 d . . . O3 O 0.0817(4) 0.5471(2) 0.3174(3) 0.1134(13) 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 Br1 0.1031(3) 0.0915(3) 0.0653(2) -0.0050(2) -0.0314(2) -0.0166(2) C1 0.0474(17) 0.0626(18) 0.0424(15) -0.0065(13) -0.0003(13) 0.0003(14) C2 0.074(2) 0.0503(17) 0.0523(17) 0.0108(14) -0.0086(16) -0.0068(16) C3 0.065(2) 0.0413(16) 0.0546(18) 0.0012(13) -0.0030(15) -0.0086(14) C4 0.0404(15) 0.0370(14) 0.0415(14) -0.0009(11) 0.0062(11) 0.0011(11) C5 0.0514(17) 0.0379(14) 0.0466(14) 0.0008(12) 0.0022(13) -0.0033(12) C6 0.0492(17) 0.0428(15) 0.0561(17) -0.0062(13) 0.0034(14) -0.0072(12) C7 0.0427(16) 0.0400(14) 0.0429(14) -0.0030(12) 0.0042(12) -0.0011(12) C8 0.0415(16) 0.0421(14) 0.0447(14) -0.0017(12) 0.0033(12) 0.0011(12) C9 0.0474(18) 0.0556(18) 0.0616(19) 0.0011(15) 0.0099(15) -0.0071(14) C10 0.050(2) 0.082(3) 0.083(3) -0.011(2) 0.0188(18) -0.0068(18) C11 0.063(2) 0.071(2) 0.088(2) -0.021(2) 0.0179(19) 0.0104(18) C12 0.0480(16) 0.0507(18) 0.0536(17) -0.0084(13) -0.0045(14) 0.0079(14) C13 0.0483(17) 0.0491(16) 0.0505(16) -0.0035(13) -0.0071(14) 0.0058(14) C14 0.067(2) 0.068(2) 0.066(2) -0.0102(17) -0.0064(18) -0.0047(19) C15 0.099(3) 0.091(3) 0.083(3) -0.024(3) -0.035(3) -0.003(3) C16 0.139(5) 0.096(3) 0.064(3) -0.011(2) -0.039(3) 0.020(3) C17 0.134(4) 0.083(3) 0.060(2) 0.020(2) -0.016(2) 0.006(3) C18 0.089(3) 0.060(2) 0.0585(19) 0.0066(15) -0.0115(18) -0.0043(18) C19 0.0383(15) 0.0495(17) 0.0593(18) -0.0114(13) 0.0044(13) 0.0000(13) N1 0.0496(17) 0.0567(17) 0.090(2) -0.0187(16) 0.0122(17) 0.0021(14) O1 0.0661(14) 0.0411(11) 0.0886(16) -0.0021(10) -0.0005(13) 0.0026(11) O2 0.075(2) 0.203(4) 0.116(3) 0.033(3) 0.044(2) 0.008(2) O3 0.0609(18) 0.0602(16) 0.219(4) 0.016(2) 0.004(2) 0.0146(14) _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 C1 1.898(3) . ? C1 C6 1.363(4) . ? C1 C2 1.376(4) . ? C2 C3 1.379(4) . ? C2 H2 0.9300 . ? C3 C4 1.374(4) . ? C3 H3 0.9300 . ? C4 C5 1.391(4) . ? C4 C7 1.517(4) . ? C5 C6 1.379(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C19 1.528(4) . ? C7 C8 1.545(4) . ? C7 H7 0.9800 . ? C8 C9 1.529(4) . ? C8 C13 1.538(4) . ? C8 C12 1.551(4) . ? C9 C10 1.514(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.519(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.490(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O1 1.199(4) . ? C13 C14 1.378(5) . ? C13 C18 1.387(5) . ? C14 C15 1.378(6) . ? C14 H14 0.9300 . ? C15 C16 1.354(7) . ? C15 H15 0.9300 . ? C16 C17 1.358(7) . ? C16 H16 0.9300 . ? C17 C18 1.384(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 N1 1.473(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? N1 O2 1.190(5) . ? N1 O3 1.209(5) . ? 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 C6 C1 C2 121.1(3) . . ? C6 C1 Br1 118.9(2) . . ? C2 C1 Br1 119.9(2) . . ? C1 C2 C3 118.8(3) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 122.1(3) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C3 C4 C5 117.2(3) . . ? C3 C4 C7 123.7(3) . . ? C5 C4 C7 119.0(2) . . ? C6 C5 C4 121.7(3) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C1 C6 C5 119.0(3) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C4 C7 C19 112.1(2) . . ? C4 C7 C8 116.2(2) . . ? C19 C7 C8 108.1(2) . . ? C4 C7 H7 106.6 . . ? C19 C7 H7 106.6 . . ? C8 C7 H7 106.6 . . ? C9 C8 C13 113.8(3) . . ? C9 C8 C7 115.0(3) . . ? C13 C8 C7 108.9(2) . . ? C9 C8 C12 101.0(2) . . ? C13 C8 C12 105.8(2) . . ? C7 C8 C12 111.7(2) . . ? C10 C9 C8 105.5(3) . . ? C10 C9 H9A 110.6 . . ? C8 C9 H9A 110.6 . . ? C10 C9 H9B 110.6 . . ? C8 C9 H9B 110.6 . . ? H9A C9 H9B 108.8 . . ? C9 C10 C11 103.6(3) . . ? C9 C10 H10A 111.0 . . ? C11 C10 H10A 111.0 . . ? C9 C10 H10B 111.0 . . ? C11 C10 H10B 111.0 . . ? H10A C10 H10B 109.0 . . ? C12 C11 C10 106.4(3) . . ? C12 C11 H11A 110.4 . . ? C10 C11 H11A 110.4 . . ? C12 C11 H11B 110.4 . . ? C10 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? O1 C12 C11 125.7(3) . . ? O1 C12 C8 125.3(3) . . ? C11 C12 C8 108.9(3) . . ? C14 C13 C18 117.0(3) . . ? C14 C13 C8 123.0(3) . . ? C18 C13 C8 119.9(3) . . ? C13 C14 C15 121.2(4) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 120.9(4) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 119.3(4) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C16 C17 C18 120.5(4) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C13 121.0(4) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? N1 C19 C7 110.3(2) . . ? N1 C19 H19A 109.6 . . ? C7 C19 H19A 109.6 . . ? N1 C19 H19B 109.6 . . ? C7 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? O2 N1 O3 123.2(4) . . ? O2 N1 C19 118.5(4) . . ? O3 N1 C19 118.3(3) . . ? 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 0.2(5) . . . . ? Br1 C1 C2 C3 178.9(3) . . . . ? C1 C2 C3 C4 -1.1(5) . . . . ? C2 C3 C4 C5 1.2(5) . . . . ? C2 C3 C4 C7 -176.1(3) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C7 C4 C5 C6 177.0(3) . . . . ? C2 C1 C6 C5 0.5(5) . . . . ? Br1 C1 C6 C5 -178.2(2) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? C3 C4 C7 C19 39.0(4) . . . . ? C5 C4 C7 C19 -138.2(3) . . . . ? C3 C4 C7 C8 -85.9(4) . . . . ? C5 C4 C7 C8 96.8(3) . . . . ? C4 C7 C8 C9 58.6(3) . . . . ? C19 C7 C8 C9 -68.4(3) . . . . ? C4 C7 C8 C13 -172.2(2) . . . . ? C19 C7 C8 C13 60.7(3) . . . . ? C4 C7 C8 C12 -55.7(3) . . . . ? C19 C7 C8 C12 177.3(2) . . . . ? C13 C8 C9 C10 77.2(3) . . . . ? C7 C8 C9 C10 -156.1(3) . . . . ? C12 C8 C9 C10 -35.7(3) . . . . ? C8 C9 C10 C11 38.0(4) . . . . ? C9 C10 C11 C12 -24.3(4) . . . . ? C10 C11 C12 O1 -179.2(3) . . . . ? C10 C11 C12 C8 2.1(4) . . . . ? C9 C8 C12 O1 -158.2(3) . . . . ? C13 C8 C12 O1 82.9(4) . . . . ? C7 C8 C12 O1 -35.5(4) . . . . ? C9 C8 C12 C11 20.5(3) . . . . ? C13 C8 C12 C11 -98.4(3) . . . . ? C7 C8 C12 C11 143.2(3) . . . . ? C9 C8 C13 C14 13.9(4) . . . . ? C7 C8 C13 C14 -116.0(3) . . . . ? C12 C8 C13 C14 123.8(3) . . . . ? C9 C8 C13 C18 -169.4(3) . . . . ? C7 C8 C13 C18 60.8(4) . . . . ? C12 C8 C13 C18 -59.4(4) . . . . ? C18 C13 C14 C15 -2.1(6) . . . . ? C8 C13 C14 C15 174.8(4) . . . . ? C13 C14 C15 C16 0.5(7) . . . . ? C14 C15 C16 C17 1.5(8) . . . . ? C15 C16 C17 C18 -1.7(8) . . . . ? C16 C17 C18 C13 0.1(7) . . . . ? C14 C13 C18 C17 1.8(6) . . . . ? C8 C13 C18 C17 -175.1(4) . . . . ? C4 C7 C19 N1 66.4(3) . . . . ? C8 C7 C19 N1 -164.2(3) . . . . ? C7 C19 N1 O2 65.5(5) . . . . ? C7 C19 N1 O3 -111.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.573 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.042 # Attachment '100302dxq-0m.cif' data_100302dxq_0m _database_code_depnum_ccdc_archive 'CCDC 768129' #TrackingRef '100302dxq-0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_absolute_configuration 9S,10S,14S _chemical_formula_sum 'C26 H27 N O2 S' _chemical_formula_weight 417.55 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.4773(6) _cell_length_b 11.8993(9) _cell_length_c 25.2455(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2246.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.166 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9550 _exptl_absorpt_correction_T_max 0.9628 _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 ? _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 13606 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.50 _reflns_number_total 4657 _reflns_number_gt 3641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0233P)^2^+0.4350P] 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 0.0031(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(7) _refine_ls_number_reflns 4657 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.003 _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 C1 C 0.4623(3) 0.63148(15) 0.05458(8) 0.0700(5) Uani 1 1 d . . . C2 C 0.3612(3) 0.55139(17) 0.02910(9) 0.0734(5) Uani 1 1 d . . . H2 H 0.2727 0.5125 0.0474 0.088 Uiso 1 1 calc R . . C3 C 0.3918(3) 0.52923(19) -0.02344(10) 0.0830(6) Uani 1 1 d . . . H3 H 0.3236 0.4744 -0.0402 0.100 Uiso 1 1 calc R . . C4 C 0.5199(3) 0.5852(2) -0.05227(9) 0.0872(7) Uani 1 1 d . . . C5 C 0.6172(4) 0.6641(2) -0.02602(11) 0.1130(9) Uani 1 1 d . . . H5 H 0.7041 0.7036 -0.0446 0.136 Uiso 1 1 calc R . . C6 C 0.5927(4) 0.68802(19) 0.02695(11) 0.0990(8) Uani 1 1 d . . . H6 H 0.6634 0.7416 0.0437 0.119 Uiso 1 1 calc R . . C7 C 0.5500(5) 0.5624(3) -0.11034(10) 0.1295(11) Uani 1 1 d . . . H7A H 0.4777 0.6126 -0.1310 0.194 Uiso 1 1 calc R . . H7B H 0.5175 0.4862 -0.1182 0.194 Uiso 1 1 calc R . . H7C H 0.6738 0.5740 -0.1188 0.194 Uiso 1 1 calc R . . C8 C 0.4893(2) 0.44515(15) 0.14954(8) 0.0607(5) Uani 1 1 d . . . H8A H 0.4918 0.4205 0.1129 0.073 Uiso 1 1 calc R . . H8B H 0.3702 0.4337 0.1638 0.073 Uiso 1 1 calc R . . C9 C 0.6285(2) 0.38494(14) 0.18220(7) 0.0554(4) Uani 1 1 d . . . H9 H 0.6037 0.4036 0.2193 0.067 Uiso 1 1 calc R . . C10 C 0.8074(2) 0.44687(17) 0.16724(7) 0.0605(5) Uani 1 1 d . . . C11 C 0.9308(3) 0.4553(2) 0.21612(8) 0.0783(6) Uani 1 1 d . . . H11A H 0.9260 0.3868 0.2369 0.094 Uiso 1 1 calc R . . H11B H 1.0536 0.4688 0.2055 0.094 Uiso 1 1 calc R . . C12 C 0.8578(3) 0.5544(2) 0.24760(9) 0.0937(8) Uani 1 1 d . . . H12A H 0.7533 0.5327 0.2680 0.112 Uiso 1 1 calc R . . H12B H 0.9477 0.5842 0.2715 0.112 Uiso 1 1 calc R . . C13 C 0.8095(3) 0.6393(2) 0.20537(10) 0.0921(7) Uani 1 1 d . . . H13A H 0.9131 0.6840 0.1957 0.110 Uiso 1 1 calc R . . H13B H 0.7160 0.6892 0.2178 0.110 Uiso 1 1 calc R . . C14 C 0.7444(3) 0.57031(17) 0.15801(8) 0.0686(5) Uani 1 1 d . . . H14 H 0.7944 0.6000 0.1250 0.082 Uiso 1 1 calc R . . C15 C 0.6248(2) 0.25895(15) 0.17837(7) 0.0548(4) Uani 1 1 d . . . C16 C 0.5807(3) 0.20137(16) 0.13248(8) 0.0701(5) Uani 1 1 d . . . H16 H 0.5546 0.2417 0.1019 0.084 Uiso 1 1 calc R . . C17 C 0.5746(3) 0.08599(18) 0.13117(10) 0.0823(6) Uani 1 1 d . . . H17 H 0.5456 0.0495 0.0998 0.099 Uiso 1 1 calc R . . C18 C 0.6110(3) 0.02420(19) 0.17569(11) 0.0872(7) Uani 1 1 d . . . H18 H 0.6045 -0.0538 0.1750 0.105 Uiso 1 1 calc R . . C19 C 0.6571(3) 0.0795(2) 0.22135(11) 0.0874(7) Uani 1 1 d . . . H19 H 0.6857 0.0385 0.2515 0.105 Uiso 1 1 calc R . . C20 C 0.6614(3) 0.19573(18) 0.22296(8) 0.0695(5) Uani 1 1 d . . . H20 H 0.6894 0.2318 0.2546 0.083 Uiso 1 1 calc R . . C21 C 0.8964(2) 0.39364(15) 0.11913(8) 0.0595(4) Uani 1 1 d . . . C22 C 0.8520(3) 0.42352(18) 0.06771(8) 0.0707(5) Uani 1 1 d . . . H22 H 0.7668 0.4792 0.0621 0.085 Uiso 1 1 calc R . . C23 C 0.9314(3) 0.3724(2) 0.02450(9) 0.0831(6) Uani 1 1 d . . . H23 H 0.8999 0.3948 -0.0095 0.100 Uiso 1 1 calc R . . C24 C 1.0540(4) 0.2906(2) 0.03123(11) 0.0961(8) Uani 1 1 d . . . H24 H 1.1069 0.2565 0.0020 0.115 Uiso 1 1 calc R . . C25 C 1.1000(3) 0.2579(2) 0.08151(12) 0.0932(7) Uani 1 1 d . . . H25 H 1.1849 0.2017 0.0863 0.112 Uiso 1 1 calc R . . C26 C 1.0209(3) 0.30814(18) 0.12526(10) 0.0780(6) Uani 1 1 d . . . H26 H 1.0518 0.2842 0.1591 0.094 Uiso 1 1 calc R . . N1 N 0.5452(2) 0.56281(13) 0.15447(7) 0.0673(4) Uani 1 1 d . . . O1 O 0.5093(3) 0.76291(12) 0.13466(7) 0.1147(7) Uani 1 1 d . . . O2 O 0.2455(2) 0.63591(14) 0.13459(7) 0.0969(5) Uani 1 1 d . . . S1 S 0.43018(9) 0.65712(5) 0.12262(2) 0.08170(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 C1 0.0780(13) 0.0502(10) 0.0818(13) 0.0080(9) -0.0077(11) 0.0006(10) C2 0.0652(12) 0.0698(13) 0.0853(15) 0.0122(11) -0.0076(11) -0.0068(11) C3 0.0847(16) 0.0797(15) 0.0846(15) 0.0011(12) -0.0124(13) -0.0142(12) C4 0.0981(18) 0.0843(15) 0.0793(15) 0.0118(12) -0.0057(13) -0.0146(14) C5 0.127(2) 0.116(2) 0.0957(19) 0.0240(17) 0.0057(17) -0.052(2) C6 0.121(2) 0.0769(15) 0.0991(18) 0.0100(13) -0.0135(16) -0.0449(15) C7 0.156(3) 0.148(3) 0.0841(18) 0.0075(17) 0.0113(19) -0.020(2) C8 0.0556(11) 0.0589(11) 0.0677(12) -0.0009(9) -0.0027(9) 0.0006(9) C9 0.0525(10) 0.0634(11) 0.0503(10) -0.0008(8) 0.0000(8) 0.0013(8) C10 0.0526(10) 0.0688(12) 0.0600(11) -0.0055(9) -0.0022(8) -0.0050(9) C11 0.0561(11) 0.1055(17) 0.0733(13) -0.0145(12) -0.0074(10) -0.0093(13) C12 0.0701(14) 0.133(2) 0.0781(15) -0.0362(15) -0.0044(12) -0.0152(15) C13 0.0782(15) 0.0931(17) 0.1049(18) -0.0375(15) -0.0006(13) -0.0145(14) C14 0.0694(12) 0.0649(12) 0.0714(13) -0.0112(10) 0.0072(10) -0.0119(10) C15 0.0443(9) 0.0625(11) 0.0575(10) 0.0084(8) 0.0041(8) 0.0025(8) C16 0.0814(13) 0.0644(11) 0.0644(12) 0.0020(9) -0.0033(11) 0.0045(10) C17 0.0888(15) 0.0680(12) 0.0901(16) -0.0091(12) 0.0033(14) -0.0002(12) C18 0.0824(16) 0.0597(13) 0.119(2) 0.0098(14) 0.0138(15) 0.0021(12) C19 0.0751(15) 0.0814(16) 0.1056(19) 0.0388(15) 0.0006(14) 0.0032(14) C20 0.0593(11) 0.0837(15) 0.0655(12) 0.0146(10) -0.0042(10) -0.0031(11) C21 0.0465(10) 0.0653(11) 0.0667(11) -0.0090(9) 0.0028(9) -0.0108(8) C22 0.0620(12) 0.0825(14) 0.0676(13) -0.0082(11) 0.0036(10) -0.0056(11) C23 0.0718(14) 0.1080(18) 0.0695(13) -0.0152(12) 0.0076(12) -0.0133(14) C24 0.0791(16) 0.117(2) 0.0924(18) -0.0344(15) 0.0126(14) -0.0043(16) C25 0.0670(14) 0.0907(17) 0.122(2) -0.0243(15) 0.0111(14) 0.0137(13) C26 0.0635(12) 0.0838(14) 0.0867(15) -0.0061(12) 0.0009(12) 0.0010(11) N1 0.0701(10) 0.0567(9) 0.0751(10) -0.0021(8) -0.0049(9) 0.0016(8) O1 0.1774(19) 0.0529(8) 0.1139(13) -0.0119(8) -0.0169(13) 0.0032(10) O2 0.0789(10) 0.1062(12) 0.1057(12) 0.0081(10) 0.0082(9) 0.0360(9) S1 0.1030(4) 0.0565(3) 0.0857(4) -0.0030(3) -0.0063(4) 0.0140(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 C1 C2 1.376(3) . ? C1 C6 1.375(3) . ? C1 S1 1.761(2) . ? C2 C3 1.372(3) . ? C2 H2 0.9300 . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 C5 1.359(3) . ? C4 C7 1.508(3) . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N1 1.467(2) . ? C8 C9 1.509(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C15 1.502(2) . ? C9 C10 1.574(2) . ? C9 H9 0.9800 . ? C10 C21 1.523(3) . ? C10 C11 1.544(3) . ? C10 C14 1.560(3) . ? C11 C12 1.524(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.512(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.530(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N1 1.494(2) . ? C14 H14 0.9800 . ? C15 C20 1.381(2) . ? C15 C16 1.386(3) . ? C16 C17 1.374(3) . ? C16 H16 0.9300 . ? C17 C18 1.370(3) . ? C17 H17 0.9300 . ? C18 C19 1.372(3) . ? C18 H18 0.9300 . ? C19 C20 1.384(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.386(3) . ? C21 C26 1.388(3) . ? C22 C23 1.382(3) . ? C22 H22 0.9300 . ? C23 C24 1.349(3) . ? C23 H23 0.9300 . ? C24 C25 1.371(4) . ? C24 H24 0.9300 . ? C25 C26 1.388(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? N1 S1 1.6268(17) . ? O1 S1 1.4237(16) . ? O2 S1 1.4359(17) . ? 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 C1 C6 119.4(2) . . ? C2 C1 S1 120.07(17) . . ? C6 C1 S1 120.44(18) . . ? C3 C2 C1 119.6(2) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 122.3(2) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C5 C4 C3 116.7(2) . . ? C5 C4 C7 121.2(2) . . ? C3 C4 C7 122.1(2) . . ? C4 C5 C6 123.0(2) . . ? C4 C5 H5 118.5 . . ? C6 C5 H5 118.5 . . ? C1 C6 C5 119.0(2) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 102.13(14) . . ? N1 C8 H8A 111.3 . . ? C9 C8 H8A 111.3 . . ? N1 C8 H8B 111.3 . . ? C9 C8 H8B 111.3 . . ? H8A C8 H8B 109.2 . . ? C15 C9 C8 115.22(15) . . ? C15 C9 C10 117.86(15) . . ? C8 C9 C10 103.48(14) . . ? C15 C9 H9 106.5 . . ? C8 C9 H9 106.5 . . ? C10 C9 H9 106.5 . . ? C21 C10 C11 113.80(16) . . ? C21 C10 C14 113.86(17) . . ? C11 C10 C14 103.81(16) . . ? C21 C10 C9 111.59(14) . . ? C11 C10 C9 110.28(16) . . ? C14 C10 C9 102.70(14) . . ? C12 C11 C10 104.66(18) . . ? C12 C11 H11A 110.8 . . ? C10 C11 H11A 110.8 . . ? C12 C11 H11B 110.8 . . ? C10 C11 H11B 110.8 . . ? H11A C11 H11B 108.9 . . ? C13 C12 C11 103.59(18) . . ? C13 C12 H12A 111.0 . . ? C11 C12 H12A 111.0 . . ? C13 C12 H12B 111.0 . . ? C11 C12 H12B 111.0 . . ? H12A C12 H12B 109.0 . . ? C12 C13 C14 105.56(19) . . ? C12 C13 H13A 110.6 . . ? C14 C13 H13A 110.6 . . ? C12 C13 H13B 110.6 . . ? C14 C13 H13B 110.6 . . ? H13A C13 H13B 108.8 . . ? N1 C14 C13 113.32(17) . . ? N1 C14 C10 104.70(16) . . ? C13 C14 C10 107.00(18) . . ? N1 C14 H14 110.5 . . ? C13 C14 H14 110.5 . . ? C10 C14 H14 110.5 . . ? C20 C15 C16 117.33(18) . . ? C20 C15 C9 119.17(17) . . ? C16 C15 C9 123.47(16) . . ? C17 C16 C15 121.5(2) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C16 120.7(2) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 118.8(2) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C18 C19 C20 120.7(2) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C15 C20 C19 121.0(2) . . ? C15 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C22 C21 C26 116.94(19) . . ? C22 C21 C10 122.39(17) . . ? C26 C21 C10 120.60(19) . . ? C23 C22 C21 121.6(2) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C24 C23 C22 120.7(2) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 119.5(2) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C24 C25 C26 120.5(2) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 120.9(2) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C8 N1 C14 110.27(15) . . ? C8 N1 S1 117.75(13) . . ? C14 N1 S1 121.02(15) . . ? O1 S1 O2 120.67(12) . . ? O1 S1 N1 106.54(10) . . ? O2 S1 N1 106.46(10) . . ? O1 S1 C1 107.75(10) . . ? O2 S1 C1 107.81(11) . . ? N1 S1 C1 106.89(9) . . ? 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(3) . . . . ? S1 C1 C2 C3 -177.62(17) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? C2 C3 C4 C5 0.5(4) . . . . ? C2 C3 C4 C7 -178.5(3) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C7 C4 C5 C6 179.5(3) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? S1 C1 C6 C5 178.5(2) . . . . ? C4 C5 C6 C1 -1.2(4) . . . . ? N1 C8 C9 C15 -171.02(15) . . . . ? N1 C8 C9 C10 -40.93(17) . . . . ? C15 C9 C10 C21 39.9(2) . . . . ? C8 C9 C10 C21 -88.56(18) . . . . ? C15 C9 C10 C11 -87.6(2) . . . . ? C8 C9 C10 C11 143.93(16) . . . . ? C15 C9 C10 C14 162.28(16) . . . . ? C8 C9 C10 C14 33.79(17) . . . . ? C21 C10 C11 C12 153.56(18) . . . . ? C14 C10 C11 C12 29.2(2) . . . . ? C9 C10 C11 C12 -80.2(2) . . . . ? C10 C11 C12 C13 -39.8(2) . . . . ? C11 C12 C13 C14 34.5(2) . . . . ? C12 C13 C14 N1 98.7(2) . . . . ? C12 C13 C14 C10 -16.2(2) . . . . ? C21 C10 C14 N1 107.10(18) . . . . ? C11 C10 C14 N1 -128.63(16) . . . . ? C9 C10 C14 N1 -13.71(19) . . . . ? C21 C10 C14 C13 -132.36(17) . . . . ? C11 C10 C14 C13 -8.1(2) . . . . ? C9 C10 C14 C13 106.83(17) . . . . ? C8 C9 C15 C20 -143.24(17) . . . . ? C10 C9 C15 C20 94.1(2) . . . . ? C8 C9 C15 C16 34.6(3) . . . . ? C10 C9 C15 C16 -88.1(2) . . . . ? C20 C15 C16 C17 -0.4(3) . . . . ? C9 C15 C16 C17 -178.31(19) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C16 C17 C18 C19 -1.3(4) . . . . ? C17 C18 C19 C20 2.0(4) . . . . ? C16 C15 C20 C19 1.1(3) . . . . ? C9 C15 C20 C19 179.11(19) . . . . ? C18 C19 C20 C15 -2.0(4) . . . . ? C11 C10 C21 C22 -148.48(19) . . . . ? C14 C10 C21 C22 -29.8(2) . . . . ? C9 C10 C21 C22 85.9(2) . . . . ? C11 C10 C21 C26 34.6(3) . . . . ? C14 C10 C21 C26 153.35(17) . . . . ? C9 C10 C21 C26 -91.0(2) . . . . ? C26 C21 C22 C23 -1.5(3) . . . . ? C10 C21 C22 C23 -178.53(18) . . . . ? C21 C22 C23 C24 0.7(3) . . . . ? C22 C23 C24 C25 0.0(4) . . . . ? C23 C24 C25 C26 0.2(4) . . . . ? C24 C25 C26 C21 -1.2(3) . . . . ? C22 C21 C26 C25 1.8(3) . . . . ? C10 C21 C26 C25 178.82(19) . . . . ? C9 C8 N1 C14 33.5(2) . . . . ? C9 C8 N1 S1 178.13(12) . . . . ? C13 C14 N1 C8 -128.17(19) . . . . ? C10 C14 N1 C8 -11.9(2) . . . . ? C13 C14 N1 S1 88.6(2) . . . . ? C10 C14 N1 S1 -155.18(13) . . . . ? C8 N1 S1 O1 179.03(15) . . . . ? C14 N1 S1 O1 -40.34(18) . . . . ? C8 N1 S1 O2 49.05(17) . . . . ? C14 N1 S1 O2 -170.32(15) . . . . ? C8 N1 S1 C1 -65.98(17) . . . . ? C14 N1 S1 C1 74.66(17) . . . . ? C2 C1 S1 O1 -162.88(16) . . . . ? C6 C1 S1 O1 19.6(2) . . . . ? C2 C1 S1 O2 -31.17(19) . . . . ? C6 C1 S1 O2 151.31(19) . . . . ? C2 C1 S1 N1 82.94(18) . . . . ? C6 C1 S1 N1 -94.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.189 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.022