Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Stuart Warren' 'Lorenzo Caggiano' 'John Davies' 'David J. Fox' 'David C. Moody' _publ_contact_author_name 'Dr Stuart Warren' _publ_contact_author_address ; University Chemical Laboratories University of Cambridge Lensfield Road Cambridge Cambridgeshire CB2 1EW UNITED KINGDOM ; _publ_contact_author_email SW134@CAM.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; A novel silica catalysed steroselective cyclic carbamate and carbonate rearrangement ; data_sw0103 _database_code_CSD 207751 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H21 N O2 S' _chemical_formula_weight 291.40 _chemical_melting_point ? _chemical_compound_source ? 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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.7248(2) _cell_length_b 13.1339(8) _cell_length_c 16.6976(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1474.78(13) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3754 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method ? _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_process_details ; Sortav Blessing (1995) multi-scan from symmetry-related measurements (Blessing 1995) ; _exptl_special_details ; Spontaneous resolution from a (+-) mixture. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6257 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2568 _reflns_number_observed 2265 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 7 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.1257P] 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 ? _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 0.04(8) _refine_ls_number_reflns 2561 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_obs 0.0371 _refine_ls_wR_factor_all 0.1473 _refine_ls_wR_factor_obs 0.0848 _refine_ls_goodness_of_fit_all 1.095 _refine_ls_goodness_of_fit_obs 1.128 _refine_ls_restrained_S_all 1.831 _refine_ls_restrained_S_obs 1.128 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.09791(8) 0.12561(4) 0.36215(3) 0.0257(2) Uani 1 d . . O1 O 0.5904(2) -0.05055(11) 0.38698(9) 0.0260(4) Uani 1 d . . O2 O 0.7585(2) -0.18128(13) 0.44101(10) 0.0324(4) Uani 1 d . . N1 N 0.4158(3) -0.16878(15) 0.44889(11) 0.0260(4) Uani 1 d . . H1 H 0.3874(3) -0.22930(15) 0.46837(11) 0.031 Uiso 1 calc R . C1 C 0.6003(3) -0.1396(2) 0.42796(13) 0.0242(5) Uani 1 d . . C2 C 0.2674(3) -0.0889(2) 0.43576(14) 0.0248(5) Uani 1 d . . H2 H 0.1488(3) -0.1201(2) 0.40922(14) 0.030 Uiso 1 calc R . C3 C 0.3822(3) -0.0252(2) 0.37260(13) 0.0218(5) Uani 1 d . . H3 H 0.3472(3) -0.0543(2) 0.31905(13) 0.026 Uiso 1 calc R . C4 C 0.2012(4) -0.0426(2) 0.51524(15) 0.0321(6) Uani 1 d . . H4A H 0.1427(22) -0.0957(3) 0.5490(4) 0.048 Uiso 1 calc R . H4B H 0.1021(18) 0.0106(8) 0.5052(2) 0.048 Uiso 1 calc R . H4C H 0.3164(5) -0.0128(11) 0.5426(5) 0.048 Uiso 1 calc R . C5 C 0.3656(3) 0.0904(2) 0.36479(13) 0.0220(5) Uani 1 d . . C6 C 0.4554(3) 0.1484(2) 0.43627(14) 0.0267(6) Uani 1 d . . H6A H 0.3730(3) 0.1353(2) 0.48431(14) 0.032 Uiso 1 calc R . H6B H 0.5903(3) 0.1215(2) 0.44700(14) 0.032 Uiso 1 calc R . C7 C 0.4694(4) 0.2638(2) 0.4232(2) 0.0331(6) Uani 1 d . . H7A H 0.3337(4) 0.2928(2) 0.4207(2) 0.040 Uiso 1 calc R . H7B H 0.5390(4) 0.2952(2) 0.4692(2) 0.040 Uiso 1 calc R . C8 C 0.5800(4) 0.2897(2) 0.3465(2) 0.0369(6) Uani 1 d . . H8A H 0.7203(4) 0.2677(2) 0.3513(2) 0.044 Uiso 1 calc R . H8B H 0.5786(4) 0.3644(2) 0.3384(2) 0.044 Uiso 1 calc R . C9 C 0.4845(4) 0.2374(2) 0.2744(2) 0.0299(6) Uani 1 d . . H9A H 0.5645(4) 0.2517(2) 0.2259(2) 0.036 Uiso 1 calc R . H9B H 0.3496(4) 0.2656(2) 0.2659(2) 0.036 Uiso 1 calc R . C10 C 0.4703(3) 0.1220(2) 0.28678(14) 0.0249(5) Uani 1 d . . H10A H 0.6062(3) 0.0931(2) 0.28665(14) 0.030 Uiso 1 calc R . H10B H 0.3974(3) 0.0920(2) 0.24096(14) 0.030 Uiso 1 calc R . C11 C 0.0108(3) 0.0838(2) 0.26737(14) 0.0237(5) Uani 1 d . . C12 C -0.0319(3) -0.0184(2) 0.25237(15) 0.0299(6) Uani 1 d . . H12 H -0.0027(3) -0.0684(2) 0.29175(15) 0.036 Uiso 1 calc R . C13 C -0.1165(4) -0.0471(2) 0.18037(15) 0.0350(6) Uani 1 d . . H13 H -0.1411(4) -0.1170(2) 0.16969(15) 0.042 Uiso 1 calc R . C14 C -0.1658(3) 0.0259(2) 0.12362(15) 0.0350(7) Uani 1 d . . H14 H -0.2284(3) 0.0063(2) 0.07500(15) 0.042 Uiso 1 calc R . C15 C -0.1235(3) 0.1269(2) 0.13814(14) 0.0324(6) Uani 1 d . . H15 H -0.1564(3) 0.1769(2) 0.09924(14) 0.039 Uiso 1 calc R . C16 C -0.0332(3) 0.1559(2) 0.20903(15) 0.0283(6) Uani 1 d . . H16 H -0.0012(3) 0.2255(2) 0.21789(15) 0.034 Uiso 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 0.0195(3) 0.0309(3) 0.0266(3) -0.0017(3) -0.0010(2) 0.0044(3) O1 0.0207(8) 0.0224(8) 0.0349(9) 0.0093(7) 0.0017(7) 0.0034(7) O2 0.0308(10) 0.0288(10) 0.0376(10) 0.0086(8) -0.0017(8) 0.0096(8) N1 0.0262(10) 0.0193(9) 0.0326(11) 0.0036(9) 0.0011(9) -0.0017(9) C1 0.0272(12) 0.0212(12) 0.0243(12) 0.0012(10) -0.0009(10) 0.0011(12) C2 0.0223(12) 0.0246(13) 0.0276(13) 0.0052(11) -0.0004(9) -0.0005(10) C3 0.0178(11) 0.0234(12) 0.0242(13) 0.0031(10) -0.0004(9) 0.0012(10) C4 0.0287(13) 0.034(2) 0.0335(14) 0.0053(13) 0.0079(11) 0.0019(11) C5 0.0165(11) 0.0224(12) 0.0271(13) 0.0028(11) -0.0002(9) 0.0019(9) C6 0.0234(11) 0.0274(14) 0.0293(14) 0.0031(11) -0.0051(10) -0.0001(10) C7 0.0378(15) 0.0252(14) 0.036(2) -0.0018(12) -0.0078(11) -0.0022(11) C8 0.0343(14) 0.0229(13) 0.053(2) 0.0046(13) -0.0013(13) -0.0034(12) C9 0.0289(14) 0.0249(14) 0.0361(15) 0.0088(12) 0.0048(10) 0.0033(10) C10 0.0221(11) 0.0238(13) 0.0287(13) 0.0040(12) 0.0031(9) 0.0015(10) C11 0.0149(11) 0.0297(13) 0.0267(13) 0.0006(11) -0.0014(9) 0.0015(10) C12 0.0278(13) 0.0301(15) 0.032(2) 0.0051(12) -0.0037(10) -0.0025(11) C13 0.0337(14) 0.0331(14) 0.038(2) -0.0019(13) -0.0051(11) -0.0079(13) C14 0.0292(13) 0.051(2) 0.0252(14) -0.0035(13) -0.0027(10) -0.0015(12) C15 0.0346(13) 0.0383(14) 0.0241(13) 0.0042(13) 0.0000(11) 0.0078(12) C16 0.0262(12) 0.0280(14) 0.0307(15) 0.0019(12) 0.0024(10) 0.0036(10) _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 C11 1.775(2) . ? S1 C5 1.860(2) . ? O1 C1 1.357(3) . ? O1 C3 1.459(3) . ? O2 C1 1.216(3) . ? N1 C1 1.344(3) . ? N1 C2 1.464(3) . ? N1 H1 0.88 . ? C2 C4 1.526(3) . ? C2 C3 1.552(3) . ? C2 H2 1.00 . ? C3 C5 1.528(3) . ? C3 H3 1.00 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 C10 1.538(3) . ? C5 C6 1.540(3) . ? C6 C7 1.534(3) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.519(4) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 C9 1.527(4) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.533(3) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C16 1.391(3) . ? C11 C12 1.395(4) . ? C12 C13 1.383(3) . ? C12 H12 0.95 . ? C13 C14 1.388(4) . ? C13 H13 0.95 . ? C14 C15 1.378(4) . ? C14 H14 0.95 . ? C15 C16 1.384(3) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? 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 C11 S1 C5 105.30(10) . . ? C1 O1 C3 109.0(2) . . ? C1 N1 C2 112.7(2) . . ? C1 N1 H1 123.64(12) . . ? C2 N1 H1 123.64(11) . . ? O2 C1 N1 129.3(2) . . ? O2 C1 O1 121.4(2) . . ? N1 C1 O1 109.4(2) . . ? N1 C2 C4 110.7(2) . . ? N1 C2 C3 98.6(2) . . ? C4 C2 C3 121.4(2) . . ? N1 C2 H2 108.44(12) . . ? C4 C2 H2 108.44(13) . . ? C3 C2 H2 108.44(11) . . ? O1 C3 C5 108.1(2) . . ? O1 C3 C2 104.1(2) . . ? C5 C3 C2 123.9(2) . . ? O1 C3 H3 106.59(10) . . ? C5 C3 H3 106.59(12) . . ? C2 C3 H3 106.59(12) . . ? C2 C4 H4A 109.47(13) . . ? C2 C4 H4B 109.47(13) . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.47(13) . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 C10 107.9(2) . . ? C3 C5 C6 113.4(2) . . ? C10 C5 C6 110.1(2) . . ? C3 C5 S1 108.64(14) . . ? C10 C5 S1 110.83(14) . . ? C6 C5 S1 105.94(14) . . ? C7 C6 C5 113.7(2) . . ? C7 C6 H6A 108.81(13) . . ? C5 C6 H6A 108.81(12) . . ? C7 C6 H6B 108.81(12) . . ? C5 C6 H6B 108.81(11) . . ? H6A C6 H6B 107.7 . . ? C8 C7 C6 111.8(2) . . ? C8 C7 H7A 109.25(14) . . ? C6 C7 H7A 109.25(12) . . ? C8 C7 H7B 109.25(13) . . ? C6 C7 H7B 109.25(13) . . ? H7A C7 H7B 107.9 . . ? C7 C8 C9 110.9(2) . . ? C7 C8 H8A 109.45(14) . . ? C9 C8 H8A 109.45(14) . . ? C7 C8 H8B 109.45(14) . . ? C9 C8 H8B 109.45(13) . . ? H8A C8 H8B 108.0 . . ? C8 C9 C10 111.4(2) . . ? C8 C9 H9A 109.34(13) . . ? C10 C9 H9A 109.34(13) . . ? C8 C9 H9B 109.34(14) . . ? C10 C9 H9B 109.34(12) . . ? H9A C9 H9B 108.0 . . ? C9 C10 C5 114.2(2) . . ? C9 C10 H10A 108.71(12) . . ? C5 C10 H10A 108.71(11) . . ? C9 C10 H10B 108.71(13) . . ? C5 C10 H10B 108.71(12) . . ? H10A C10 H10B 107.6 . . ? C16 C11 C12 119.1(2) . . ? C16 C11 S1 118.9(2) . . ? C12 C11 S1 121.7(2) . . ? C13 C12 C11 120.2(2) . . ? C13 C12 H12 119.9(2) . . ? C11 C12 H12 119.90(14) . . ? C12 C13 C14 120.2(2) . . ? C12 C13 H13 119.9(2) . . ? C14 C13 H13 119.9(2) . . ? C15 C14 C13 119.7(2) . . ? C15 C14 H14 120.15(15) . . ? C13 C14 H14 120.15(15) . . ? C14 C15 C16 120.4(2) . . ? C14 C15 H15 119.80(15) . . ? C16 C15 H15 119.80(15) . . ? C15 C16 C11 120.3(2) . . ? C15 C16 H16 119.84(15) . . ? C11 C16 H16 119.84(14) . . ? 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 C2 N1 C1 O2 168.9(2) . . . . ? C2 N1 C1 O1 -11.0(3) . . . . ? C3 O1 C1 O2 173.5(2) . . . . ? C3 O1 C1 N1 -6.5(2) . . . . ? C1 N1 C2 C4 -106.5(2) . . . . ? C1 N1 C2 C3 21.9(2) . . . . ? C1 O1 C3 C5 153.2(2) . . . . ? C1 O1 C3 C2 19.9(2) . . . . ? N1 C2 C3 O1 -23.7(2) . . . . ? C4 C2 C3 O1 97.0(2) . . . . ? N1 C2 C3 C5 -147.3(2) . . . . ? C4 C2 C3 C5 -26.6(3) . . . . ? O1 C3 C5 C10 68.4(2) . . . . ? C2 C3 C5 C10 -169.9(2) . . . . ? O1 C3 C5 C6 -53.9(2) . . . . ? C2 C3 C5 C6 67.9(3) . . . . ? O1 C3 C5 S1 -171.41(13) . . . . ? C2 C3 C5 S1 -49.6(2) . . . . ? C11 S1 C5 C3 -71.4(2) . . . . ? C11 S1 C5 C10 47.0(2) . . . . ? C11 S1 C5 C6 166.4(2) . . . . ? C3 C5 C6 C7 170.9(2) . . . . ? C10 C5 C6 C7 49.8(2) . . . . ? S1 C5 C6 C7 -70.1(2) . . . . ? C5 C6 C7 C8 -54.0(3) . . . . ? C6 C7 C8 C9 55.5(3) . . . . ? C7 C8 C9 C10 -55.2(3) . . . . ? C8 C9 C10 C5 53.6(3) . . . . ? C3 C5 C10 C9 -174.2(2) . . . . ? C6 C5 C10 C9 -50.0(2) . . . . ? S1 C5 C10 C9 66.9(2) . . . . ? C5 S1 C11 C16 -108.3(2) . . . . ? C5 S1 C11 C12 77.7(2) . . . . ? C16 C11 C12 C13 0.1(3) . . . . ? S1 C11 C12 C13 174.1(2) . . . . ? C11 C12 C13 C14 -2.2(4) . . . . ? C12 C13 C14 C15 2.3(4) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C11 -1.8(3) . . . . ? C12 C11 C16 C15 1.9(3) . . . . ? S1 C11 C16 C15 -172.3(2) . . . . ? _refine_diff_density_max 0.232 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.073 data_sw0104 _database_code_CSD 207752 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H21 N O2 S' _chemical_formula_weight 291.40 _chemical_melting_point ? _chemical_compound_source ? 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.8413(3) _cell_length_b 14.7036(9) _cell_length_c 19.2137(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.201(3) _cell_angle_gamma 90.00 _cell_volume 3062.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8002 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method ? _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_process_details ; Sortav Blessing (1995) multi-scan from symmetry-related measurements (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18109 _diffrn_reflns_av_R_equivalents 0.0965 _diffrn_reflns_av_sigmaI/netI 0.1077 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5375 _reflns_number_observed 3265 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 17 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0477P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5358 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1185 _refine_ls_R_factor_obs 0.0523 _refine_ls_wR_factor_all 0.1927 _refine_ls_wR_factor_obs 0.0950 _refine_ls_goodness_of_fit_all 1.005 _refine_ls_goodness_of_fit_obs 1.105 _refine_ls_restrained_S_all 1.710 _refine_ls_restrained_S_obs 1.105 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1_1 S -0.12743(5) 0.36397(5) 0.35543(4) 0.0352(2) Uani 1 d . . O1_1 O -0.24836(12) 0.43888(12) 0.21835(9) 0.0300(4) Uani 1 d . . O2_1 O -0.34499(13) 0.57018(11) 0.22844(9) 0.0310(4) Uani 1 d . . N1_1 N -0.1491(2) 0.56140(14) 0.26912(10) 0.0296(5) Uani 1 d . . H1_1 H -0.1535(2) 0.61882(14) 0.28180(10) 0.036 Uiso 1 calc R . C1_1 C -0.2494(2) 0.5266(2) 0.23817(12) 0.0260(6) Uani 1 d . . C2_1 C -0.0326(2) 0.5143(2) 0.28421(13) 0.0276(6) Uani 1 d . . H2_1 H 0.0276(2) 0.5322(2) 0.24734(13) 0.033 Uiso 1 calc R . C3_1 C -0.0535(2) 0.4121(2) 0.27779(12) 0.0267(6) Uani 1 d . . H3_1 H 0.0290(2) 0.3825(2) 0.27273(12) 0.032 Uiso 1 calc R . C4_1 C -0.1282(2) 0.3917(2) 0.21161(13) 0.0292(6) Uani 1 d . . C5_1 C 0.0177(2) 0.5480(2) 0.35308(14) 0.0379(7) Uani 1 d . . H5A_1 H 0.0282(13) 0.6141(2) 0.3512(3) 0.057 Uiso 1 calc R . H5B_1 H 0.0976(7) 0.5192(8) 0.3624(4) 0.057 Uiso 1 calc R . H5C_1 H -0.0401(7) 0.5325(9) 0.3903(2) 0.057 Uiso 1 calc R . C6_1 C -0.1607(2) 0.2919(2) 0.20299(14) 0.0371(7) Uani 1 d . . H6A_1 H -0.2120(2) 0.2726(2) 0.24291(14) 0.044 Uiso 1 calc R . H6B_1 H -0.0838(2) 0.2556(2) 0.20417(14) 0.044 Uiso 1 calc R . C7_1 C -0.2301(2) 0.2707(2) 0.13559(15) 0.0454(8) Uani 1 d . . H7A_1 H -0.2425(2) 0.2042(2) 0.13159(15) 0.055 Uiso 1 calc R . H7B_1 H -0.3123(2) 0.3000(2) 0.13675(15) 0.055 Uiso 1 calc R . C8_1 C -0.1594(3) 0.3047(2) 0.0730(2) 0.0549(9) Uani 1 d . . H8A_1 H -0.2077(3) 0.2928(2) 0.0301(2) 0.066 Uiso 1 calc R . H8B_1 H -0.0803(3) 0.2714(2) 0.0694(2) 0.066 Uiso 1 calc R . C9_1 C -0.1342(2) 0.4060(2) 0.07938(14) 0.0471(8) Uani 1 d . . H9A_1 H -0.2134(2) 0.4395(2) 0.07897(14) 0.057 Uiso 1 calc R . H9B_1 H -0.0853(2) 0.4265(2) 0.03890(14) 0.057 Uiso 1 calc R . C10_1 C -0.0640(2) 0.4277(2) 0.14643(13) 0.0353(7) Uani 1 d . . H10A_1 H -0.0546(2) 0.4945(2) 0.15052(13) 0.042 Uiso 1 calc R . H10B_1 H 0.0196(2) 0.4009(2) 0.14368(13) 0.042 Uiso 1 calc R . C11_1 C 0.0016(2) 0.3150(2) 0.39949(14) 0.0329(7) Uani 1 d . . C12_1 C 0.0667(2) 0.2438(2) 0.3695(2) 0.0433(8) Uani 1 d . . H12_1 H 0.0436(2) 0.2213(2) 0.3250(2) 0.052 Uiso 1 calc R . C13_1 C 0.1655(3) 0.2058(2) 0.4048(2) 0.0524(8) Uani 1 d . . H13_1 H 0.2118(3) 0.1584(2) 0.3839(2) 0.063 Uiso 1 calc R . C14_1 C 0.1970(3) 0.2366(2) 0.4706(2) 0.0525(9) Uani 1 d . . H14_1 H 0.2640(3) 0.2097(2) 0.4951(2) 0.063 Uiso 1 calc R . C15_1 C 0.1314(2) 0.3061(2) 0.5004(2) 0.0499(8) Uani 1 d . . H15_1 H 0.1527(2) 0.3270(2) 0.5456(2) 0.060 Uiso 1 calc R . C16_1 C 0.0341(2) 0.3459(2) 0.46470(14) 0.0401(7) Uani 1 d . . H16_1 H -0.0103(2) 0.3946(2) 0.48526(14) 0.048 Uiso 1 calc R . S1_2 S 0.33090(6) 0.42710(5) 0.34809(4) 0.0380(2) Uani 1 d . . O1_2 O 0.24788(13) 0.38624(12) 0.19702(9) 0.0334(5) Uani 1 d . . O2_2 O 0.16353(14) 0.24990(12) 0.19355(9) 0.0378(5) Uani 1 d . . N1_2 N 0.35369(15) 0.26225(14) 0.24096(10) 0.0284(5) Uani 1 d . . H1_2 H 0.35401(15) 0.20323(14) 0.24855(10) 0.034 Uiso 1 calc R . C1_2 C 0.2536(2) 0.2964(2) 0.20989(13) 0.0290(6) Uani 1 d . . C2_2 C 0.4634(2) 0.3130(2) 0.26381(13) 0.0290(6) Uani 1 d . . H2_2 H 0.5265(2) 0.3086(2) 0.22612(13) 0.035 Uiso 1 calc R . C3_2 C 0.4265(2) 0.4123(2) 0.27069(13) 0.0279(6) Uani 1 d . . H3_2 H 0.5030(2) 0.4497(2) 0.27633(13) 0.033 Uiso 1 calc R . C4_2 C 0.3604(2) 0.4423(2) 0.20412(13) 0.0297(6) Uani 1 d . . C5_2 C 0.5172(2) 0.2697(2) 0.32848(14) 0.0434(8) Uani 1 d . . H5A_2 H 0.5378(13) 0.2061(3) 0.3188(3) 0.065 Uiso 1 calc R . H5B_2 H 0.4566(6) 0.2725(10) 0.3662(3) 0.065 Uiso 1 calc R . H5C_2 H 0.5919(9) 0.3026(7) 0.3424(5) 0.065 Uiso 1 calc R . C6_2 C 0.3162(2) 0.5403(2) 0.20819(14) 0.0376(7) Uani 1 d . . H6A_2 H 0.3873(2) 0.5796(2) 0.22038(14) 0.045 Uiso 1 calc R . H6B_2 H 0.2552(2) 0.5454(2) 0.24621(14) 0.045 Uiso 1 calc R . C7_2 C 0.2578(3) 0.5758(2) 0.1412(2) 0.0543(9) Uani 1 d . . H7A_2 H 0.1791(3) 0.5435(2) 0.1326(2) 0.065 Uiso 1 calc R . H7B_2 H 0.2392(3) 0.6414(2) 0.1465(2) 0.065 Uiso 1 calc R . C8_2 C 0.3424(3) 0.5624(2) 0.0797(2) 0.0623(10) Uani 1 d . . H8A_2 H 0.4180(3) 0.5993(2) 0.0860(2) 0.075 Uiso 1 calc R . H8B_2 H 0.3005(3) 0.5830(2) 0.0366(2) 0.075 Uiso 1 calc R . C9_2 C 0.3767(3) 0.4625(2) 0.0731(2) 0.0562(9) Uani 1 d . . H9A_2 H 0.3013(3) 0.4263(2) 0.0637(2) 0.067 Uiso 1 calc R . H9B_2 H 0.4333(3) 0.4545(2) 0.0333(2) 0.067 Uiso 1 calc R . C10_2 C 0.4385(2) 0.4276(2) 0.13906(13) 0.0375(7) Uani 1 d . . H10A_2 H 0.5186(2) 0.4590(2) 0.14517(13) 0.045 Uiso 1 calc R . H10B_2 H 0.4554(2) 0.3618(2) 0.13379(13) 0.045 Uiso 1 calc R . C11_2 C 0.3930(2) 0.5207(2) 0.39459(13) 0.0296(6) Uani 1 d . . C12_2 C 0.4866(2) 0.5779(2) 0.37280(14) 0.0349(7) Uani 1 d . . H12_2 H 0.5240(2) 0.5688(2) 0.32869(14) 0.042 Uiso 1 calc R . C13_2 C 0.5259(2) 0.6483(2) 0.41512(15) 0.0414(7) Uani 1 d . . H13_2 H 0.5911(2) 0.6866(2) 0.40010(15) 0.050 Uiso 1 calc R . C14_2 C 0.4719(3) 0.6635(2) 0.4786(2) 0.0475(8) Uani 1 d . . H14_2 H 0.4986(3) 0.7124(2) 0.5072(2) 0.057 Uiso 1 calc R . C15_2 C 0.3787(3) 0.6069(2) 0.50012(15) 0.0496(8) Uani 1 d . . H15_2 H 0.3412(3) 0.6167(2) 0.54410(15) 0.059 Uiso 1 calc R . C16_2 C 0.3388(2) 0.5360(2) 0.45887(14) 0.0409(7) Uani 1 d . . H16_2 H 0.2742(2) 0.4975(2) 0.47447(14) 0.049 Uiso 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_1 0.0286(4) 0.0395(5) 0.0376(4) 0.0034(4) 0.0032(3) -0.0009(3) O1_1 0.0219(9) 0.0240(12) 0.0441(12) -0.0087(9) -0.0034(7) 0.0023(7) O2_1 0.0220(9) 0.0260(11) 0.0449(12) -0.0030(9) -0.0033(7) 0.0050(8) N1_1 0.0260(11) 0.0205(14) 0.0424(14) -0.0035(11) -0.0053(9) 0.0016(9) C1_1 0.0270(14) 0.025(2) 0.026(2) -0.0005(13) 0.0008(11) -0.0009(12) C2_1 0.0219(13) 0.026(2) 0.035(2) -0.0012(13) -0.0023(10) 0.0022(11) C3_1 0.0200(12) 0.030(2) 0.030(2) -0.0009(13) 0.0012(10) 0.0044(11) C4_1 0.0226(13) 0.030(2) 0.035(2) -0.0050(13) -0.0017(11) 0.0065(11) C5_1 0.0354(15) 0.031(2) 0.048(2) -0.0066(15) -0.0084(12) 0.0012(12) C6_1 0.0330(14) 0.031(2) 0.047(2) -0.0107(14) -0.0059(12) 0.0069(12) C7_1 0.041(2) 0.035(2) 0.060(2) -0.019(2) -0.0125(15) 0.0060(13) C8_1 0.052(2) 0.060(3) 0.052(2) -0.024(2) -0.0177(15) 0.015(2) C9_1 0.043(2) 0.061(2) 0.037(2) -0.004(2) -0.0034(13) 0.0073(15) C10_1 0.0285(14) 0.044(2) 0.033(2) -0.0027(14) -0.0021(11) 0.0063(12) C11_1 0.0331(14) 0.032(2) 0.034(2) 0.0064(14) 0.0040(12) -0.0024(13) C12_1 0.048(2) 0.037(2) 0.045(2) 0.001(2) -0.0049(14) 0.0019(14) C13_1 0.056(2) 0.041(2) 0.060(2) 0.005(2) -0.001(2) 0.012(2) C14_1 0.047(2) 0.053(2) 0.058(2) 0.025(2) -0.007(2) 0.002(2) C15_1 0.051(2) 0.062(2) 0.037(2) 0.007(2) -0.0061(14) -0.001(2) C16_1 0.040(2) 0.043(2) 0.037(2) 0.0002(15) 0.0050(13) -0.0005(13) S1_2 0.0378(4) 0.0319(5) 0.0444(5) -0.0055(4) 0.0131(3) -0.0059(3) O1_2 0.0244(9) 0.0221(12) 0.0537(13) 0.0070(9) -0.0085(8) -0.0046(7) O2_2 0.0289(9) 0.0273(12) 0.0571(13) 0.0060(10) -0.0099(8) -0.0074(8) N1_2 0.0262(11) 0.0179(13) 0.0412(14) -0.0003(11) -0.0055(9) 0.0009(9) C1_2 0.0275(15) 0.026(2) 0.034(2) 0.0024(13) -0.0001(11) -0.0004(13) C2_2 0.0235(13) 0.025(2) 0.038(2) -0.0045(13) -0.0008(11) -0.0001(11) C3_2 0.0213(13) 0.027(2) 0.036(2) -0.0032(13) 0.0022(10) -0.0012(11) C4_2 0.0248(13) 0.024(2) 0.040(2) 0.0024(13) -0.0034(11) -0.0070(11) C5_2 0.042(2) 0.033(2) 0.055(2) -0.004(2) -0.0182(13) 0.0056(13) C6_2 0.0339(14) 0.022(2) 0.057(2) 0.0038(15) -0.0049(12) -0.0039(12) C7_2 0.056(2) 0.030(2) 0.077(3) 0.012(2) -0.026(2) -0.0108(15) C8_2 0.098(3) 0.042(2) 0.047(2) 0.016(2) -0.036(2) -0.025(2) C9_2 0.074(2) 0.054(2) 0.041(2) 0.000(2) -0.011(2) -0.025(2) C10_2 0.0377(15) 0.038(2) 0.037(2) -0.0023(14) -0.0013(12) -0.0113(13) C11_2 0.0288(14) 0.027(2) 0.033(2) 0.0006(13) -0.0015(11) 0.0060(12) C12_2 0.042(2) 0.031(2) 0.032(2) -0.0009(14) 0.0039(12) -0.0010(13) C13_2 0.047(2) 0.037(2) 0.039(2) -0.001(2) -0.0007(14) -0.0072(14) C14_2 0.063(2) 0.046(2) 0.034(2) -0.012(2) -0.0037(15) -0.003(2) C15_2 0.059(2) 0.062(2) 0.029(2) -0.007(2) 0.0073(14) 0.001(2) C16_2 0.040(2) 0.045(2) 0.038(2) 0.001(2) 0.0042(13) -0.0021(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 S1_1 C11_1 1.784(3) . ? S1_1 C3_1 1.837(2) . ? O1_1 C1_1 1.344(3) . ? O1_1 C4_1 1.482(3) . ? O2_1 C1_1 1.233(3) . ? N1_1 C1_1 1.339(3) . ? N1_1 C2_1 1.468(3) . ? N1_1 H1_1 0.88 . ? C2_1 C5_1 1.513(3) . ? C2_1 C3_1 1.525(3) . ? C2_1 H2_1 1.00 . ? C3_1 C4_1 1.534(3) . ? C3_1 H3_1 1.00 . ? C4_1 C6_1 1.520(3) . ? C4_1 C10_1 1.529(3) . ? C5_1 H5A_1 0.98 . ? C5_1 H5B_1 0.98 . ? C5_1 H5C_1 0.98 . ? C6_1 C7_1 1.527(3) . ? C6_1 H6A_1 0.99 . ? C6_1 H6B_1 0.99 . ? C7_1 C8_1 1.514(4) . ? C7_1 H7A_1 0.99 . ? C7_1 H7B_1 0.99 . ? C8_1 C9_1 1.520(4) . ? C8_1 H8A_1 0.99 . ? C8_1 H8B_1 0.99 . ? C9_1 C10_1 1.528(3) . ? C9_1 H9A_1 0.99 . ? C9_1 H9B_1 0.99 . ? C10_1 H10A_1 0.99 . ? C10_1 H10B_1 0.99 . ? C11_1 C16_1 1.377(4) . ? C11_1 C12_1 1.389(4) . ? C12_1 C13_1 1.384(4) . ? C12_1 H12_1 0.95 . ? C13_1 C14_1 1.384(4) . ? C13_1 H13_1 0.95 . ? C14_1 C15_1 1.371(4) . ? C14_1 H14_1 0.95 . ? C15_1 C16_1 1.386(4) . ? C15_1 H15_1 0.95 . ? C16_1 H16_1 0.95 . ? S1_2 C11_2 1.773(3) . ? S1_2 C3_2 1.829(2) . ? O1_2 C1_2 1.345(3) . ? O1_2 C4_2 1.478(3) . ? O2_2 C1_2 1.232(3) . ? N1_2 C1_2 1.334(3) . ? N1_2 C2_2 1.470(3) . ? N1_2 H1_2 0.88 . ? C2_2 C5_2 1.511(3) . ? C2_2 C3_2 1.520(3) . ? C2_2 H2_2 1.00 . ? C3_2 C4_2 1.529(3) . ? C3_2 H3_2 1.00 . ? C4_2 C6_2 1.520(3) . ? C4_2 C10_2 1.528(3) . ? C5_2 H5A_2 0.98 . ? C5_2 H5B_2 0.98 . ? C5_2 H5C_2 0.98 . ? C6_2 C7_2 1.524(4) . ? C6_2 H6A_2 0.99 . ? C6_2 H6B_2 0.99 . ? C7_2 C8_2 1.511(4) . ? C7_2 H7A_2 0.99 . ? C7_2 H7B_2 0.99 . ? C8_2 C9_2 1.522(4) . ? C8_2 H8A_2 0.99 . ? C8_2 H8B_2 0.99 . ? C9_2 C10_2 1.521(4) . ? C9_2 H9A_2 0.99 . ? C9_2 H9B_2 0.99 . ? C10_2 H10A_2 0.99 . ? C10_2 H10B_2 0.99 . ? C11_2 C12_2 1.384(3) . ? C11_2 C16_2 1.388(3) . ? C12_2 C13_2 1.382(4) . ? C12_2 H12_2 0.95 . ? C13_2 C14_2 1.372(4) . ? C13_2 H13_2 0.95 . ? C14_2 C15_2 1.374(4) . ? C14_2 H14_2 0.95 . ? C15_2 C16_2 1.378(4) . ? C15_2 H15_2 0.95 . ? C16_2 H16_2 0.95 . ? 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 C11_1 S1_1 C3_1 101.37(11) . . ? C1_1 O1_1 C4_1 118.8(2) . . ? C1_1 N1_1 C2_1 127.1(2) . . ? C1_1 N1_1 H1_1 116.43(14) . . ? C2_1 N1_1 H1_1 116.43(12) . . ? O2_1 C1_1 N1_1 123.3(2) . . ? O2_1 C1_1 O1_1 117.6(2) . . ? N1_1 C1_1 O1_1 119.0(2) . . ? N1_1 C2_1 C5_1 109.0(2) . . ? N1_1 C2_1 C3_1 108.7(2) . . ? C5_1 C2_1 C3_1 116.5(2) . . ? N1_1 C2_1 H2_1 107.42(12) . . ? C5_1 C2_1 H2_1 107.42(13) . . ? C3_1 C2_1 H2_1 107.42(12) . . ? C2_1 C3_1 C4_1 109.7(2) . . ? C2_1 C3_1 S1_1 112.3(2) . . ? C4_1 C3_1 S1_1 111.6(2) . . ? C2_1 C3_1 H3_1 107.70(11) . . ? C4_1 C3_1 H3_1 107.70(12) . . ? S1_1 C3_1 H3_1 107.70(7) . . ? O1_1 C4_1 C6_1 104.9(2) . . ? O1_1 C4_1 C10_1 108.2(2) . . ? C6_1 C4_1 C10_1 110.6(2) . . ? O1_1 C4_1 C3_1 107.3(2) . . ? C6_1 C4_1 C3_1 113.6(2) . . ? C10_1 C4_1 C3_1 111.8(2) . . ? C2_1 C5_1 H5A_1 109.47(14) . . ? C2_1 C5_1 H5B_1 109.47(13) . . ? H5A_1 C5_1 H5B_1 109.5 . . ? C2_1 C5_1 H5C_1 109.47(13) . . ? H5A_1 C5_1 H5C_1 109.5 . . ? H5B_1 C5_1 H5C_1 109.5 . . ? C4_1 C6_1 C7_1 113.7(2) . . ? C4_1 C6_1 H6A_1 108.81(14) . . ? C7_1 C6_1 H6A_1 108.81(15) . . ? C4_1 C6_1 H6B_1 108.81(12) . . ? C7_1 C6_1 H6B_1 108.81(14) . . ? H6A_1 C6_1 H6B_1 107.7 . . ? C8_1 C7_1 C6_1 110.9(2) . . ? C8_1 C7_1 H7A_1 109.5(2) . . ? C6_1 C7_1 H7A_1 109.5(2) . . ? C8_1 C7_1 H7B_1 109.5(2) . . ? C6_1 C7_1 H7B_1 109.45(14) . . ? H7A_1 C7_1 H7B_1 108.0 . . ? C7_1 C8_1 C9_1 110.5(2) . . ? C7_1 C8_1 H8A_1 109.55(15) . . ? C9_1 C8_1 H8A_1 109.55(15) . . ? C7_1 C8_1 H8B_1 109.5(2) . . ? C9_1 C8_1 H8B_1 109.55(14) . . ? H8A_1 C8_1 H8B_1 108.1 . . ? C8_1 C9_1 C10_1 111.2(2) . . ? C8_1 C9_1 H9A_1 109.39(14) . . ? C10_1 C9_1 H9A_1 109.39(14) . . ? C8_1 C9_1 H9B_1 109.4(2) . . ? C10_1 C9_1 H9B_1 109.39(14) . . ? H9A_1 C9_1 H9B_1 108.0 . . ? C9_1 C10_1 C4_1 113.0(2) . . ? C9_1 C10_1 H10A_1 109.0(2) . . ? C4_1 C10_1 H10A_1 108.97(14) . . ? C9_1 C10_1 H10B_1 108.97(14) . . ? C4_1 C10_1 H10B_1 108.97(12) . . ? H10A_1 C10_1 H10B_1 107.8 . . ? C16_1 C11_1 C12_1 119.8(2) . . ? C16_1 C11_1 S1_1 119.7(2) . . ? C12_1 C11_1 S1_1 120.4(2) . . ? C13_1 C12_1 C11_1 119.6(3) . . ? C13_1 C12_1 H12_1 120.2(2) . . ? C11_1 C12_1 H12_1 120.2(2) . . ? C12_1 C13_1 C14_1 120.3(3) . . ? C12_1 C13_1 H13_1 119.9(2) . . ? C14_1 C13_1 H13_1 119.9(2) . . ? C15_1 C14_1 C13_1 119.9(3) . . ? C15_1 C14_1 H14_1 120.1(2) . . ? C13_1 C14_1 H14_1 120.1(2) . . ? C14_1 C15_1 C16_1 120.2(3) . . ? C14_1 C15_1 H15_1 119.9(2) . . ? C16_1 C15_1 H15_1 119.9(2) . . ? C11_1 C16_1 C15_1 120.2(3) . . ? C11_1 C16_1 H16_1 119.9(2) . . ? C15_1 C16_1 H16_1 119.9(2) . . ? C11_2 S1_2 C3_2 106.67(12) . . ? C1_2 O1_2 C4_2 119.5(2) . . ? C1_2 N1_2 C2_2 126.7(2) . . ? C1_2 N1_2 H1_2 116.64(14) . . ? C2_2 N1_2 H1_2 116.64(12) . . ? O2_2 C1_2 N1_2 123.2(2) . . ? O2_2 C1_2 O1_2 117.5(2) . . ? N1_2 C1_2 O1_2 119.3(2) . . ? N1_2 C2_2 C5_2 110.0(2) . . ? N1_2 C2_2 C3_2 107.5(2) . . ? C5_2 C2_2 C3_2 115.7(2) . . ? N1_2 C2_2 H2_2 107.79(12) . . ? C5_2 C2_2 H2_2 107.79(14) . . ? C3_2 C2_2 H2_2 107.79(13) . . ? C2_2 C3_2 C4_2 109.1(2) . . ? C2_2 C3_2 S1_2 109.6(2) . . ? C4_2 C3_2 S1_2 112.4(2) . . ? C2_2 C3_2 H3_2 108.59(12) . . ? C4_2 C3_2 H3_2 108.59(12) . . ? S1_2 C3_2 H3_2 108.58(8) . . ? O1_2 C4_2 C6_2 105.9(2) . . ? O1_2 C4_2 C10_2 107.8(2) . . ? C6_2 C4_2 C10_2 110.6(2) . . ? O1_2 C4_2 C3_2 107.5(2) . . ? C6_2 C4_2 C3_2 112.1(2) . . ? C10_2 C4_2 C3_2 112.6(2) . . ? C2_2 C5_2 H5A_2 109.47(14) . . ? C2_2 C5_2 H5B_2 109.47(14) . . ? H5A_2 C5_2 H5B_2 109.5 . . ? C2_2 C5_2 H5C_2 109.47(13) . . ? H5A_2 C5_2 H5C_2 109.5 . . ? H5B_2 C5_2 H5C_2 109.5 . . ? C4_2 C6_2 C7_2 114.3(2) . . ? C4_2 C6_2 H6A_2 108.69(12) . . ? C7_2 C6_2 H6A_2 108.69(14) . . ? C4_2 C6_2 H6B_2 108.69(14) . . ? C7_2 C6_2 H6B_2 108.7(2) . . ? H6A_2 C6_2 H6B_2 107.6 . . ? C8_2 C7_2 C6_2 111.4(2) . . ? C8_2 C7_2 H7A_2 109.4(2) . . ? C6_2 C7_2 H7A_2 109.36(14) . . ? C8_2 C7_2 H7B_2 109.4(2) . . ? C6_2 C7_2 H7B_2 109.4(2) . . ? H7A_2 C7_2 H7B_2 108.0 . . ? C7_2 C8_2 C9_2 109.9(3) . . ? C7_2 C8_2 H8A_2 109.7(2) . . ? C9_2 C8_2 H8A_2 109.7(2) . . ? C7_2 C8_2 H8B_2 109.7(2) . . ? C9_2 C8_2 H8B_2 109.7(2) . . ? H8A_2 C8_2 H8B_2 108.2 . . ? C10_2 C9_2 C8_2 111.3(2) . . ? C10_2 C9_2 H9A_2 109.37(15) . . ? C8_2 C9_2 H9A_2 109.4(2) . . ? C10_2 C9_2 H9B_2 109.4(2) . . ? C8_2 C9_2 H9B_2 109.4(2) . . ? H9A_2 C9_2 H9B_2 108.0 . . ? C9_2 C10_2 C4_2 113.0(2) . . ? C9_2 C10_2 H10A_2 108.99(15) . . ? C4_2 C10_2 H10A_2 108.99(13) . . ? C9_2 C10_2 H10B_2 109.0(2) . . ? C4_2 C10_2 H10B_2 108.99(14) . . ? H10A_2 C10_2 H10B_2 107.8 . . ? C12_2 C11_2 C16_2 118.9(2) . . ? C12_2 C11_2 S1_2 126.6(2) . . ? C16_2 C11_2 S1_2 114.4(2) . . ? C13_2 C12_2 C11_2 120.1(2) . . ? C13_2 C12_2 H12_2 120.0(2) . . ? C11_2 C12_2 H12_2 120.0(2) . . ? C14_2 C13_2 C12_2 120.9(3) . . ? C14_2 C13_2 H13_2 119.5(2) . . ? C12_2 C13_2 H13_2 119.5(2) . . ? C13_2 C14_2 C15_2 119.0(3) . . ? C13_2 C14_2 H14_2 120.5(2) . . ? C15_2 C14_2 H14_2 120.5(2) . . ? C14_2 C15_2 C16_2 120.9(3) . . ? C14_2 C15_2 H15_2 119.5(2) . . ? C16_2 C15_2 H15_2 119.5(2) . . ? C15_2 C16_2 C11_2 120.1(3) . . ? C15_2 C16_2 H16_2 119.9(2) . . ? C11_2 C16_2 H16_2 119.9(2) . . ? 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 C2_1 N1_1 C1_1 O2_1 178.6(2) . . . . ? C2_1 N1_1 C1_1 O1_1 0.7(4) . . . . ? C4_1 O1_1 C1_1 O2_1 163.9(2) . . . . ? C4_1 O1_1 C1_1 N1_1 -18.1(3) . . . . ? C1_1 N1_1 C2_1 C5_1 -143.6(2) . . . . ? C1_1 N1_1 C2_1 C3_1 -15.6(3) . . . . ? N1_1 C2_1 C3_1 C4_1 45.0(2) . . . . ? C5_1 C2_1 C3_1 C4_1 168.6(2) . . . . ? N1_1 C2_1 C3_1 S1_1 -79.7(2) . . . . ? C5_1 C2_1 C3_1 S1_1 43.9(2) . . . . ? C11_1 S1_1 C3_1 C2_1 -100.7(2) . . . . ? C11_1 S1_1 C3_1 C4_1 135.7(2) . . . . ? C1_1 O1_1 C4_1 C6_1 169.1(2) . . . . ? C1_1 O1_1 C4_1 C10_1 -72.8(3) . . . . ? C1_1 O1_1 C4_1 C3_1 48.0(3) . . . . ? C2_1 C3_1 C4_1 O1_1 -60.9(2) . . . . ? S1_1 C3_1 C4_1 O1_1 64.2(2) . . . . ? C2_1 C3_1 C4_1 C6_1 -176.4(2) . . . . ? S1_1 C3_1 C4_1 C6_1 -51.3(2) . . . . ? C2_1 C3_1 C4_1 C10_1 57.7(2) . . . . ? S1_1 C3_1 C4_1 C10_1 -177.3(2) . . . . ? O1_1 C4_1 C6_1 C7_1 65.6(3) . . . . ? C10_1 C4_1 C6_1 C7_1 -50.9(3) . . . . ? C3_1 C4_1 C6_1 C7_1 -177.5(2) . . . . ? C4_1 C6_1 C7_1 C8_1 54.7(3) . . . . ? C6_1 C7_1 C8_1 C9_1 -56.7(3) . . . . ? C7_1 C8_1 C9_1 C10_1 57.0(3) . . . . ? C8_1 C9_1 C10_1 C4_1 -54.6(3) . . . . ? O1_1 C4_1 C10_1 C9_1 -63.8(3) . . . . ? C6_1 C4_1 C10_1 C9_1 50.7(3) . . . . ? C3_1 C4_1 C10_1 C9_1 178.3(2) . . . . ? C3_1 S1_1 C11_1 C16_1 118.2(2) . . . . ? C3_1 S1_1 C11_1 C12_1 -64.0(2) . . . . ? C16_1 C11_1 C12_1 C13_1 -1.4(4) . . . . ? S1_1 C11_1 C12_1 C13_1 -179.1(2) . . . . ? C11_1 C12_1 C13_1 C14_1 2.0(4) . . . . ? C12_1 C13_1 C14_1 C15_1 -1.1(4) . . . . ? C13_1 C14_1 C15_1 C16_1 -0.4(4) . . . . ? C12_1 C11_1 C16_1 C15_1 -0.1(4) . . . . ? S1_1 C11_1 C16_1 C15_1 177.6(2) . . . . ? C14_1 C15_1 C16_1 C11_1 1.0(4) . . . . ? C2_2 N1_2 C1_2 O2_2 -178.3(2) . . . . ? C2_2 N1_2 C1_2 O1_2 -0.1(4) . . . . ? C4_2 O1_2 C1_2 O2_2 -169.4(2) . . . . ? C4_2 O1_2 C1_2 N1_2 12.3(3) . . . . ? C1_2 N1_2 C2_2 C5_2 147.1(2) . . . . ? C1_2 N1_2 C2_2 C3_2 20.4(3) . . . . ? N1_2 C2_2 C3_2 C4_2 -50.1(2) . . . . ? C5_2 C2_2 C3_2 C4_2 -173.4(2) . . . . ? N1_2 C2_2 C3_2 S1_2 73.3(2) . . . . ? C5_2 C2_2 C3_2 S1_2 -50.0(2) . . . . ? C11_2 S1_2 C3_2 C2_2 131.2(2) . . . . ? C11_2 S1_2 C3_2 C4_2 -107.4(2) . . . . ? C1_2 O1_2 C4_2 C6_2 -163.1(2) . . . . ? C1_2 O1_2 C4_2 C10_2 78.6(3) . . . . ? C1_2 O1_2 C4_2 C3_2 -43.0(3) . . . . ? C2_2 C3_2 C4_2 O1_2 61.9(2) . . . . ? S1_2 C3_2 C4_2 O1_2 -59.8(2) . . . . ? C2_2 C3_2 C4_2 C6_2 177.8(2) . . . . ? S1_2 C3_2 C4_2 C6_2 56.1(2) . . . . ? C2_2 C3_2 C4_2 C10_2 -56.7(3) . . . . ? S1_2 C3_2 C4_2 C10_2 -178.4(2) . . . . ? O1_2 C4_2 C6_2 C7_2 -67.2(3) . . . . ? C10_2 C4_2 C6_2 C7_2 49.3(3) . . . . ? C3_2 C4_2 C6_2 C7_2 175.8(2) . . . . ? C4_2 C6_2 C7_2 C8_2 -53.5(3) . . . . ? C6_2 C7_2 C8_2 C9_2 56.3(3) . . . . ? C7_2 C8_2 C9_2 C10_2 -58.0(3) . . . . ? C8_2 C9_2 C10_2 C4_2 55.7(3) . . . . ? O1_2 C4_2 C10_2 C9_2 65.1(3) . . . . ? C6_2 C4_2 C10_2 C9_2 -50.2(3) . . . . ? C3_2 C4_2 C10_2 C9_2 -176.5(2) . . . . ? C3_2 S1_2 C11_2 C12_2 6.6(3) . . . . ? C3_2 S1_2 C11_2 C16_2 -173.8(2) . . . . ? C16_2 C11_2 C12_2 C13_2 0.7(4) . . . . ? S1_2 C11_2 C12_2 C13_2 -179.7(2) . . . . ? C11_2 C12_2 C13_2 C14_2 -1.0(4) . . . . ? C12_2 C13_2 C14_2 C15_2 0.8(4) . . . . ? C13_2 C14_2 C15_2 C16_2 -0.4(4) . . . . ? C14_2 C15_2 C16_2 C11_2 0.1(4) . . . . ? C12_2 C11_2 C16_2 C15_2 -0.3(4) . . . . ? S1_2 C11_2 C16_2 C15_2 -179.9(2) . . . . ? _refine_diff_density_max 0.219 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.057