# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email xpzhang@usf.edu _publ_contact_author_name 'Peter Zhang' loop_ _publ_author_name 'Peter Zhang' 'Hongjian Lu' 'Huiling Jiang' 'Yang Hu' 'Lukasz Wojtas' data_hjl_3_252_0m _database_code_depnum_ccdc_archive 'CCDC 830353' #TrackingRef '- Xray 2o.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 N2 O2 S' _chemical_formula_sum 'C17 H18 N2 O2 S' _chemical_formula_weight 314.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 34.0823(7) _cell_length_b 5.4014(1) _cell_length_c 16.6312(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.680(1) _cell_angle_gamma 90.00 _cell_volume 2987.0(1) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4203 _cell_measurement_theta_min 5.3 _cell_measurement_theta_max 65.5 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 1.999 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7536 _exptl_absorpt_correction_T_max 0.9067 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXII CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11857 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.32 _diffrn_reflns_theta_max 65.94 _reflns_number_total 2549 _reflns_number_gt 2249 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _publ_section_references ; Bruker AXS. (2010). APEX2 Bruker AXS, Inc. Madison, Wisconsin, USA. Bruker AXS. (2009). SAINT Bruker AXS, Inc. Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _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^)+(0.0518P)^2^+1.7344P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2549 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0900 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.119983(11) 1.13147(7) 0.93817(2) 0.01577(14) Uani 1 1 d . . . O1 O 0.10443(3) 1.3700(2) 0.91052(8) 0.0216(3) Uani 1 1 d . . . O2 O 0.13526(3) 1.0865(2) 1.02377(7) 0.0216(3) Uani 1 1 d . . . N1 N 0.15556(4) 1.0697(3) 0.88761(8) 0.0158(3) Uani 1 1 d . . . N2 N 0.08398(4) 0.9327(3) 0.90515(9) 0.0168(3) Uani 1 1 d . . . H2N H 0.0905(6) 0.797(4) 0.9238(12) 0.017(5) Uiso 1 1 d . . . C1 C 0.29314(5) 0.8125(4) 0.85202(11) 0.0233(4) Uani 1 1 d . . . H1 H 0.3192 0.8044 0.8406 0.028 Uiso 1 1 calc R . . C2 C 0.26575(5) 0.6247(3) 0.82573(11) 0.0237(4) Uani 1 1 d . . . H2 H 0.2728 0.4895 0.7952 0.028 Uiso 1 1 calc R . . C3 C 0.22787(5) 0.6341(3) 0.84399(11) 0.0209(4) Uani 1 1 d . . . H3 H 0.2092 0.5045 0.8260 0.025 Uiso 1 1 calc R . . C4 C 0.21719(5) 0.8309(3) 0.88819(10) 0.0163(3) Uani 1 1 d . . . C5 C 0.17730(5) 0.8343(3) 0.91346(11) 0.0182(4) Uani 1 1 d . . . H5A H 0.1607 0.6928 0.8877 0.022 Uiso 1 1 calc R . . H5B H 0.1818 0.8163 0.9740 0.022 Uiso 1 1 calc R . . C6 C 0.13845(5) 1.0797(3) 0.79716(10) 0.0169(4) Uani 1 1 d . . . H6A H 0.1599 1.0381 0.7679 0.020 Uiso 1 1 calc R . . H6B H 0.1296 1.2513 0.7820 0.020 Uiso 1 1 calc R . . C7 C 0.10316(5) 0.9065(3) 0.76767(10) 0.0158(3) Uani 1 1 d . . . C8 C 0.10222(5) 0.7608(3) 0.70241(10) 0.0174(4) Uani 1 1 d . . . H8 H 0.1256 0.7647 0.6803 0.021 Uiso 1 1 calc R . . C9 C 0.06985(5) 0.5943(3) 0.65982(10) 0.0168(3) Uani 1 1 d . . . C10 C 0.08044(5) 0.3845(3) 0.62019(10) 0.0181(4) Uani 1 1 d . . . H10 H 0.1079 0.3580 0.6190 0.022 Uiso 1 1 calc R . . C11 C 0.05186(5) 0.2148(3) 0.58263(10) 0.0199(4) Uani 1 1 d . . . H11 H 0.0598 0.0713 0.5573 0.024 Uiso 1 1 calc R . . C12 C 0.01153(5) 0.2539(3) 0.58190(10) 0.0204(4) Uani 1 1 d . . . H12 H -0.0081 0.1357 0.5573 0.024 Uiso 1 1 calc R . . C13 C 0.28255(5) 1.0130(3) 0.89507(11) 0.0228(4) Uani 1 1 d . . . H13 H 0.3012 1.1435 0.9124 0.027 Uiso 1 1 calc R . . C14 C 0.24470(5) 1.0214(3) 0.91253(10) 0.0196(4) Uani 1 1 d . . . H14 H 0.2374 1.1593 0.9415 0.024 Uiso 1 1 calc R . . C15 C 0.06978(5) 0.9265(3) 0.81389(10) 0.0181(3) Uani 1 1 d . . . H15A H 0.0542 1.0789 0.7960 0.022 Uiso 1 1 calc R . . H15B H 0.0514 0.7838 0.7988 0.022 Uiso 1 1 calc R . . C16 C 0.02887(5) 0.6359(3) 0.65542(10) 0.0188(4) Uani 1 1 d . . . H16 H 0.0206 0.7820 0.6789 0.023 Uiso 1 1 calc R . . C17 C 0.00021(5) 0.4665(3) 0.61727(10) 0.0206(4) Uani 1 1 d . . . H17 H -0.0274 0.4967 0.6154 0.025 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 0.0146(2) 0.0158(2) 0.0180(2) -0.00241(14) 0.00571(16) -0.00157(14) O1 0.0197(6) 0.0172(6) 0.0293(7) -0.0024(5) 0.0081(5) -0.0001(4) O2 0.0205(6) 0.0271(7) 0.0181(6) -0.0038(5) 0.0059(5) -0.0028(5) N1 0.0141(7) 0.0172(7) 0.0165(7) 0.0015(5) 0.0047(5) 0.0000(5) N2 0.0181(7) 0.0153(8) 0.0183(8) 0.0008(6) 0.0069(6) -0.0019(6) C1 0.0155(8) 0.0316(10) 0.0233(9) 0.0046(7) 0.0057(7) 0.0033(7) C2 0.0241(9) 0.0223(10) 0.0260(10) -0.0016(7) 0.0087(8) 0.0045(7) C3 0.0212(9) 0.0166(9) 0.0249(9) -0.0012(7) 0.0048(7) -0.0016(6) C4 0.0159(8) 0.0187(8) 0.0133(8) 0.0028(6) 0.0013(6) 0.0016(6) C5 0.0174(8) 0.0176(9) 0.0199(9) 0.0028(6) 0.0049(7) 0.0009(6) C6 0.0158(8) 0.0186(9) 0.0172(9) 0.0018(6) 0.0057(6) -0.0019(6) C7 0.0153(8) 0.0150(8) 0.0167(8) 0.0036(6) 0.0027(6) 0.0000(6) C8 0.0149(8) 0.0207(9) 0.0170(8) 0.0041(6) 0.0045(6) 0.0010(6) C9 0.0189(8) 0.0186(9) 0.0129(8) 0.0024(6) 0.0040(6) -0.0001(6) C10 0.0157(8) 0.0244(9) 0.0146(8) 0.0011(6) 0.0043(6) 0.0025(6) C11 0.0253(9) 0.0192(9) 0.0157(8) -0.0015(6) 0.0054(7) 0.0029(7) C12 0.0229(9) 0.0198(9) 0.0178(8) -0.0017(6) 0.0029(7) -0.0037(7) C13 0.0165(9) 0.0265(10) 0.0229(9) 0.0001(7) -0.0014(7) -0.0049(7) C14 0.0196(9) 0.0204(9) 0.0173(8) -0.0030(6) 0.0007(7) 0.0001(6) C15 0.0149(8) 0.0210(9) 0.0184(9) -0.0026(6) 0.0035(7) -0.0022(6) C16 0.0197(9) 0.0191(9) 0.0177(8) -0.0008(6) 0.0046(7) 0.0021(6) C17 0.0153(8) 0.0254(9) 0.0211(9) -0.0002(7) 0.0037(7) 0.0009(7) _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 O2 1.4253(13) . ? S1 O1 1.4301(12) . ? S1 N2 1.6323(14) . ? S1 N1 1.6540(13) . ? N1 C5 1.487(2) . ? N1 C6 1.490(2) . ? N2 C15 1.489(2) . ? N2 H2N 0.81(2) . ? C1 C2 1.383(3) . ? C1 C13 1.389(3) . ? C1 H1 0.9500 . ? C2 C3 1.391(2) . ? C2 H2 0.9500 . ? C3 C4 1.385(2) . ? C3 H3 0.9500 . ? C4 C14 1.391(2) . ? C4 C5 1.509(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.517(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.335(2) . ? C7 C15 1.510(2) . ? C8 C9 1.478(2) . ? C8 H8 0.9500 . ? C9 C10 1.398(2) . ? C9 C16 1.401(2) . ? C10 C11 1.383(2) . ? C10 H10 0.9500 . ? C11 C12 1.388(2) . ? C11 H11 0.9500 . ? C12 C17 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.384(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.386(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? 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 O2 S1 O1 120.21(7) . . ? O2 S1 N2 107.86(7) . . ? O1 S1 N2 106.64(8) . . ? O2 S1 N1 108.99(7) . . ? O1 S1 N1 106.23(7) . . ? N2 S1 N1 106.08(7) . . ? C5 N1 C6 112.48(13) . . ? C5 N1 S1 113.58(10) . . ? C6 N1 S1 109.75(10) . . ? C15 N2 S1 114.21(11) . . ? C15 N2 H2N 111.8(14) . . ? S1 N2 H2N 110.2(14) . . ? C2 C1 C13 120.06(16) . . ? C2 C1 H1 120.0 . . ? C13 C1 H1 120.0 . . ? C1 C2 C3 119.92(16) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.56(16) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C14 118.89(15) . . ? C3 C4 C5 120.98(15) . . ? C14 C4 C5 120.06(15) . . ? N1 C5 C4 110.64(13) . . ? N1 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N1 C6 C7 114.25(13) . . ? N1 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? N1 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C15 124.71(15) . . ? C8 C7 C6 120.12(14) . . ? C15 C7 C6 115.07(14) . . ? C7 C8 C9 129.08(15) . . ? C7 C8 H8 115.5 . . ? C9 C8 H8 115.5 . . ? C10 C9 C16 117.59(15) . . ? C10 C9 C8 118.45(15) . . ? C16 C9 C8 123.94(15) . . ? C11 C10 C9 121.42(15) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 120.06(15) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C17 C12 C11 119.38(15) . . ? C17 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C14 C13 C1 119.58(16) . . ? C14 C13 H13 120.2 . . ? C1 C13 H13 120.2 . . ? C13 C14 C4 120.95(16) . . ? C13 C14 H14 119.5 . . ? C4 C14 H14 119.5 . . ? N2 C15 C7 114.06(13) . . ? N2 C15 H15A 108.7 . . ? C7 C15 H15A 108.7 . . ? N2 C15 H15B 108.7 . . ? C7 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C17 C16 C9 120.82(16) . . ? C17 C16 H16 119.6 . . ? C9 C16 H16 119.6 . . ? C12 C17 C16 120.56(16) . . ? C12 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 65.94 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.255 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.049 # Attachment '- Xray cis,trans-2e.cif' data_hjl_8_118 _database_code_depnum_ccdc_archive 'CCDC 830354' #TrackingRef '- Xray cis,trans-2e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 N2 O2 S' _chemical_formula_sum 'C16 H22 N2 O2 S' _chemical_formula_weight 306.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall -P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 12.3076(3) _cell_length_b 9.7760(3) _cell_length_c 26.6952(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3211.94(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4696 _cell_measurement_theta_min 3.31 _cell_measurement_theta_max 66.25 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 1.837 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8096 _exptl_absorpt_correction_T_max 0.9301 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXII CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32841 _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 67.12 _reflns_number_total 2859 _reflns_number_gt 2398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _publ_section_references ; Bruker AXS. (2010). APEX2 Bruker AXS, Inc. Madison, Wisconsin, USA. Bruker AXS. (2009). SAINT Bruker AXS, Inc. Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _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^)+(0.0557P)^2^+1.6968P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2859 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 S1 S 0.28053(3) 0.05056(4) 0.410352(16) 0.02063(16) Uani 1 1 d . . . O1 O 0.16832(11) 0.05422(14) 0.39685(5) 0.0276(3) Uani 1 1 d . . . O2 O 0.31945(11) -0.07391(13) 0.43283(5) 0.0269(3) Uani 1 1 d . . . N1 N 0.35155(13) 0.08796(16) 0.35991(6) 0.0247(4) Uani 1 1 d . . . N2 N 0.30579(13) 0.17375(16) 0.44842(6) 0.0212(3) Uani 1 1 d . . . H2 H 0.2672(19) 0.245(3) 0.4413(9) 0.032 Uiso 1 1 d . . . C1 C 0.4269(2) 0.1577(3) 0.17749(9) 0.0551(8) Uani 1 1 d . . . H1 H 0.4475 0.1942 0.1467 0.066 Uiso 1 1 calc R . . C2 C 0.4754(2) 0.0406(3) 0.19486(9) 0.0508(7) Uani 1 1 d . . . H2A H 0.5286 -0.0024 0.1758 0.061 Uiso 1 1 calc R . . C3 C 0.44542(19) -0.0136(3) 0.24043(8) 0.0398(5) Uani 1 1 d . . . H3 H 0.4790 -0.0928 0.2519 0.048 Uiso 1 1 calc R . . C4 C 0.36601(17) 0.0481(2) 0.26931(7) 0.0287(5) Uani 1 1 d . . . C5 C 0.33231(18) -0.0113(2) 0.31871(7) 0.0300(5) Uani 1 1 d . . . H5A H 0.2558 -0.0350 0.3176 0.036 Uiso 1 1 calc R . . H5B H 0.3733 -0.0942 0.3251 0.036 Uiso 1 1 calc R . . C6 C 0.46700(15) 0.1262(2) 0.36863(7) 0.0257(4) Uani 1 1 d . . . H6 H 0.4938 0.1627 0.3367 0.031 Uiso 1 1 calc R . . C7 C 0.47586(15) 0.2435(2) 0.40654(7) 0.0241(4) Uani 1 1 d . . . H7 H 0.4360 0.3216 0.3926 0.029 Uiso 1 1 calc R . . C8 C 0.42186(15) 0.20661(19) 0.45703(7) 0.0234(4) Uani 1 1 d . . . H8 H 0.4583 0.1264 0.4713 0.028 Uiso 1 1 calc R . . C9 C 0.42637(16) 0.3220(2) 0.49412(7) 0.0270(4) Uani 1 1 d . . . H9 H 0.3845 0.3992 0.4877 0.032 Uiso 1 1 calc R . . C10 C 0.48522(18) 0.3209(2) 0.53476(8) 0.0325(5) Uani 1 1 d . . . H10A H 0.5280 0.2453 0.5423 0.039 Uiso 1 1 calc R . . H10B H 0.4844 0.3959 0.5562 0.039 Uiso 1 1 calc R . . C11 C 0.3477(2) 0.2213(3) 0.20560(9) 0.0501(7) Uani 1 1 d . . . H11 H 0.3149 0.3008 0.1939 0.060 Uiso 1 1 calc R . . C12 C 0.31702(19) 0.1668(2) 0.25141(8) 0.0364(5) Uani 1 1 d . . . H12 H 0.2634 0.2097 0.2703 0.044 Uiso 1 1 calc R . . C13 C 0.59488(17) 0.2867(2) 0.41155(8) 0.0311(5) Uani 1 1 d . . . H13A H 0.6184 0.3277 0.3803 0.037 Uiso 1 1 calc R . . H13B H 0.6007 0.3557 0.4375 0.037 Uiso 1 1 calc R . . C14 C 0.67054(18) 0.1677(2) 0.42436(9) 0.0391(5) Uani 1 1 d . . . H14A H 0.7451 0.1999 0.4250 0.047 Uiso 1 1 calc R . . H14B H 0.6529 0.1329 0.4574 0.047 Uiso 1 1 calc R . . C15 C 0.65961(18) 0.0534(2) 0.38605(10) 0.0424(6) Uani 1 1 d . . . H15A H 0.7049 -0.0232 0.3959 0.051 Uiso 1 1 calc R . . H15B H 0.6846 0.0855 0.3537 0.051 Uiso 1 1 calc R . . C16 C 0.54175(18) 0.0062(2) 0.38182(9) 0.0342(5) Uani 1 1 d . . . H16A H 0.5189 -0.0337 0.4134 0.041 Uiso 1 1 calc R . . H16B H 0.5361 -0.0636 0.3561 0.041 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 0.0199(3) 0.0199(3) 0.0221(3) 0.00021(17) 0.00194(16) -0.00186(17) O1 0.0220(7) 0.0331(8) 0.0278(7) -0.0028(6) 0.0003(5) -0.0032(6) O2 0.0279(7) 0.0209(7) 0.0320(8) 0.0026(5) 0.0028(6) -0.0026(6) N1 0.0260(9) 0.0247(8) 0.0234(8) -0.0031(6) 0.0040(6) -0.0058(7) N2 0.0222(8) 0.0187(8) 0.0226(8) 0.0008(6) 0.0013(6) 0.0011(6) C1 0.085(2) 0.0569(16) 0.0235(12) -0.0076(11) 0.0082(12) -0.0392(15) C2 0.0562(16) 0.0610(17) 0.0353(13) -0.0188(12) 0.0190(11) -0.0220(13) C3 0.0386(13) 0.0473(13) 0.0334(12) -0.0125(10) 0.0049(10) -0.0050(11) C4 0.0284(11) 0.0332(11) 0.0246(10) -0.0069(8) 0.0015(8) -0.0110(9) C5 0.0344(12) 0.0277(10) 0.0280(11) -0.0053(8) 0.0043(8) -0.0056(9) C6 0.0207(10) 0.0290(10) 0.0274(10) 0.0010(8) 0.0044(8) -0.0026(8) C7 0.0224(10) 0.0228(9) 0.0271(10) 0.0031(8) 0.0000(8) -0.0007(8) C8 0.0203(10) 0.0230(9) 0.0269(10) 0.0022(8) -0.0012(7) 0.0013(7) C9 0.0260(11) 0.0257(10) 0.0294(10) 0.0020(8) -0.0015(8) -0.0010(8) C10 0.0361(12) 0.0314(11) 0.0299(11) 0.0022(9) -0.0033(9) -0.0028(9) C11 0.0740(19) 0.0406(13) 0.0357(13) 0.0043(11) -0.0107(12) -0.0185(13) C12 0.0405(13) 0.0355(12) 0.0333(12) -0.0039(10) -0.0008(9) -0.0063(10) C13 0.0258(11) 0.0327(11) 0.0349(11) 0.0016(9) 0.0017(8) -0.0060(9) C14 0.0210(10) 0.0488(14) 0.0475(13) 0.0060(11) -0.0019(9) 0.0007(10) C15 0.0258(11) 0.0443(13) 0.0570(15) 0.0058(11) 0.0057(10) 0.0093(10) C16 0.0311(11) 0.0283(10) 0.0432(12) -0.0018(9) 0.0062(9) 0.0025(9) _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 1.4277(14) . ? S1 O2 1.4388(14) . ? S1 N2 1.6062(16) . ? S1 N1 1.6466(16) . ? N1 C5 1.485(2) . ? N1 C6 1.488(2) . ? N2 C8 1.482(2) . ? N2 H2 0.87(3) . ? C1 C2 1.372(4) . ? C1 C11 1.378(4) . ? C1 H1 0.9300 . ? C2 C3 1.377(4) . ? C2 H2A 0.9300 . ? C3 C4 1.383(3) . ? C3 H3 0.9300 . ? C4 C12 1.392(3) . ? C4 C5 1.499(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C16 1.532(3) . ? C6 C7 1.533(3) . ? C6 H6 0.9800 . ? C7 C13 1.530(3) . ? C7 C8 1.546(3) . ? C7 H7 0.9800 . ? C8 C9 1.502(3) . ? C8 H8 0.9800 . ? C9 C10 1.305(3) . ? C9 H9 0.9300 . ? C10 H10A 0.9300 . ? C10 H10B 0.9300 . ? C11 C12 1.387(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.528(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.521(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.526(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? 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 116.65(8) . . ? O1 S1 N2 109.16(8) . . ? O2 S1 N2 107.81(8) . . ? O1 S1 N1 107.54(8) . . ? O2 S1 N1 110.62(8) . . ? N2 S1 N1 104.37(8) . . ? C5 N1 C6 115.61(15) . . ? C5 N1 S1 112.08(12) . . ? C6 N1 S1 115.78(13) . . ? C8 N2 S1 116.57(12) . . ? C8 N2 H2 112.7(16) . . ? S1 N2 H2 111.2(16) . . ? C2 C1 C11 120.0(2) . . ? C2 C1 H1 120.0 . . ? C11 C1 H1 120.0 . . ? C1 C2 C3 120.2(2) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C2 C3 C4 120.9(2) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C12 118.6(2) . . ? C3 C4 C5 121.1(2) . . ? C12 C4 C5 120.31(19) . . ? N1 C5 C4 110.75(16) . . ? N1 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N1 C6 C16 114.65(16) . . ? N1 C6 C7 111.05(15) . . ? C16 C6 C7 112.23(17) . . ? N1 C6 H6 106.1 . . ? C16 C6 H6 106.1 . . ? C7 C6 H6 106.1 . . ? C13 C7 C6 109.39(16) . . ? C13 C7 C8 113.56(16) . . ? C6 C7 C8 111.74(15) . . ? C13 C7 H7 107.3 . . ? C6 C7 H7 107.3 . . ? C8 C7 H7 107.3 . . ? N2 C8 C9 107.49(15) . . ? N2 C8 C7 109.26(15) . . ? C9 C8 C7 112.56(15) . . ? N2 C8 H8 109.2 . . ? C9 C8 H8 109.2 . . ? C7 C8 H8 109.2 . . ? C10 C9 C8 124.25(19) . . ? C10 C9 H9 117.9 . . ? C8 C9 H9 117.9 . . ? C9 C10 H10A 120.0 . . ? C9 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? C1 C11 C12 120.0(2) . . ? C1 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C4 120.3(2) . . ? C11 C12 H12 119.8 . . ? C4 C12 H12 119.8 . . ? C14 C13 C7 113.14(17) . . ? C14 C13 H13A 109.0 . . ? C7 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C7 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 110.78(19) . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C14 C15 C16 110.85(18) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C6 110.88(17) . . ? C15 C16 H16A 109.5 . . ? C6 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C6 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 67.12 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.333 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.049 # Attachment '- Xray cis-2c.cif' data_3y _database_code_depnum_ccdc_archive 'CCDC 830355' #TrackingRef '- Xray cis-2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N2 O2 S' _chemical_formula_weight 202.27 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 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 5.20710(10) _cell_length_b 12.8881(3) _cell_length_c 14.6972(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 986.32(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4887 _cell_measurement_theta_min 3.007 _cell_measurement_theta_max 67.1556 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 2.698 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4117 _exptl_absorpt_correction_T_max 0.8769 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXII CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8608 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.56 _diffrn_reflns_theta_max 67.64 _reflns_number_total 1742 _reflns_number_gt 1675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0721P)^2^+0.0384P] 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 0.0028(6) _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, 681 Friedel Pairs' _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_number_reflns 1742 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 S1 S 0.87142(9) 0.31724(4) 0.73867(4) 0.0476(2) Uani 1 1 d . . . C1 C 0.5999(6) 0.2524(2) 0.88136(17) 0.0657(7) Uani 1 1 d . . . H1A H 0.4519 0.2714 0.8449 0.079 Uiso 1 1 calc R . . H1B H 0.6299 0.3060 0.9264 0.079 Uiso 1 1 calc R . . N1 N 0.8290(4) 0.23695(15) 0.82358(13) 0.0515(5) Uani 1 1 d . . . O1 O 1.1270(3) 0.30051(14) 0.70666(14) 0.0652(5) Uani 1 1 d . . . C2 C 0.5606(7) 0.1485(3) 0.9260(2) 0.0915(11) Uani 1 1 d . . . H2A H 0.3863 0.1244 0.9161 0.110 Uiso 1 1 calc R . . H2B H 0.5900 0.1537 0.9910 0.110 Uiso 1 1 calc R . . N2 N 0.6814(3) 0.28066(13) 0.65704(12) 0.0449(4) Uani 1 1 d . . . H2N H 0.5060 0.3019 0.6620 0.054 Uiso 1 1 d R . . O2 O 0.7949(4) 0.41788(13) 0.76738(16) 0.0702(5) Uani 1 1 d . . . C3 C 0.7518(7) 0.0732(3) 0.8834(2) 0.0790(9) Uani 1 1 d . . . H3A H 0.8968 0.0617 0.9236 0.095 Uiso 1 1 calc R . . H3B H 0.6707 0.0070 0.8707 0.095 Uiso 1 1 calc R . . C4 C 0.8373(5) 0.12526(18) 0.79617(16) 0.0536(5) Uani 1 1 d . . . H4 H 1.0142 0.1051 0.7819 0.064 Uiso 1 1 calc R . . C5 C 0.6615(5) 0.09993(16) 0.71576(15) 0.0490(5) Uani 1 1 d . . . H5A H 0.6873 0.0281 0.6984 0.059 Uiso 1 1 calc R . . H5B H 0.4842 0.1075 0.7349 0.059 Uiso 1 1 calc R . . C6 C 0.7083(4) 0.16894(17) 0.63296(14) 0.0459(5) Uani 1 1 d . . . H6 H 0.8858 0.1577 0.6131 0.055 Uiso 1 1 calc R . . C7 C 0.5374(5) 0.1487(2) 0.55299(16) 0.0560(6) Uani 1 1 d . . . H7 H 0.5628 0.1898 0.5018 0.067 Uiso 1 1 calc R . . C8 C 0.3562(7) 0.0788(2) 0.54804(18) 0.0646(6) Uani 1 1 d . . . H8A H 0.3236 0.0357 0.5975 0.077 Uiso 1 1 calc R . . H8B H 0.2599 0.0721 0.4951 0.077 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 0.0311(3) 0.0423(3) 0.0695(3) -0.0043(2) 0.0024(2) -0.00213(18) C1 0.0566(15) 0.0842(18) 0.0564(13) -0.0103(12) 0.0075(12) -0.0014(14) N1 0.0362(9) 0.0588(11) 0.0597(10) -0.0067(9) -0.0047(8) 0.0031(8) O1 0.0305(8) 0.0695(11) 0.0955(12) -0.0017(9) 0.0077(8) -0.0054(8) C2 0.087(2) 0.123(3) 0.0642(17) 0.0101(17) 0.0131(15) -0.018(2) N2 0.0340(9) 0.0413(9) 0.0595(10) 0.0052(7) 0.0045(7) 0.0022(7) O2 0.0606(10) 0.0456(9) 0.1043(14) -0.0167(9) 0.0022(10) -0.0022(8) C3 0.083(2) 0.083(2) 0.0710(17) 0.0265(15) -0.0130(16) 0.0008(16) C4 0.0456(12) 0.0524(13) 0.0627(12) 0.0095(10) -0.0075(10) 0.0064(10) C5 0.0473(11) 0.0376(10) 0.0620(12) 0.0017(8) -0.0017(10) 0.0026(9) C6 0.0387(10) 0.0463(11) 0.0529(11) -0.0024(9) 0.0072(8) 0.0025(8) C7 0.0591(15) 0.0600(14) 0.0490(13) -0.0026(10) 0.0040(10) 0.0019(11) C8 0.0727(17) 0.0616(14) 0.0594(13) -0.0112(10) -0.0086(13) 0.0015(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 O2 1.4210(18) . ? S1 O1 1.4277(17) . ? S1 N2 1.6249(19) . ? S1 N1 1.636(2) . ? C1 N1 1.478(3) . ? C1 C2 1.505(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? N1 C4 1.495(3) . ? C2 C3 1.525(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N2 C6 1.489(3) . ? N2 H2N 0.9563 . ? C3 C4 1.514(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.530(3) . ? C4 H4 0.9800 . ? C5 C6 1.527(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.497(3) . ? C6 H6 0.9800 . ? C7 C8 1.306(4) . ? C7 H7 0.9300 . ? C8 H8A 0.9300 . ? C8 H8B 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 119.81(11) . . ? O2 S1 N2 108.26(11) . . ? O1 S1 N2 106.28(11) . . ? O2 S1 N1 108.24(12) . . ? O1 S1 N1 106.35(11) . . ? N2 S1 N1 107.31(9) . . ? N1 C1 C2 103.9(2) . . ? N1 C1 H1A 111.0 . . ? C2 C1 H1A 111.0 . . ? N1 C1 H1B 111.0 . . ? C2 C1 H1B 111.0 . . ? H1A C1 H1B 109.0 . . ? C1 N1 C4 107.9(2) . . ? C1 N1 S1 117.52(17) . . ? C4 N1 S1 113.55(15) . . ? C1 C2 C3 107.4(2) . . ? C1 C2 H2A 110.2 . . ? C3 C2 H2A 110.2 . . ? C1 C2 H2B 110.2 . . ? C3 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? C6 N2 S1 113.50(14) . . ? C6 N2 H2N 112.6 . . ? S1 N2 H2N 116.3 . . ? C4 C3 C2 104.9(3) . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.8 . . ? N1 C4 C3 101.0(2) . . ? N1 C4 C5 113.34(18) . . ? C3 C4 C5 112.6(2) . . ? N1 C4 H4 109.9 . . ? C3 C4 H4 109.9 . . ? C5 C4 H4 109.9 . . ? C6 C5 C4 113.32(19) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? N2 C6 C7 107.44(18) . . ? N2 C6 C5 111.02(17) . . ? C7 C6 C5 115.41(19) . . ? N2 C6 H6 107.6 . . ? C7 C6 H6 107.6 . . ? C5 C6 H6 107.6 . . ? C8 C7 C6 126.4(2) . . ? C8 C7 H7 116.8 . . ? C6 C7 H7 116.8 . . ? C7 C8 H8A 120.0 . . ? C7 C8 H8B 120.0 . . ? H8A C8 H8B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 67.64 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.245 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.043 # Attachment '- Xray trans,cis-2d.cif' data_hl_8_79_2_0m _database_code_depnum_ccdc_archive 'CCDC 830356' #TrackingRef '- Xray trans,cis-2d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 N2 O2 S' _chemical_formula_sum 'C16 H22 N2 O2 S' _chemical_formula_weight 306.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 14.5628(4) _cell_length_b 6.4095(2) _cell_length_c 16.6818(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.174(2) _cell_angle_gamma 90.00 _cell_volume 1522.07(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3740 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 65.88 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.939 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7597 _exptl_absorpt_correction_T_max 0.9623 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXII CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12157 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 65.97 _reflns_number_total 2598 _reflns_number_gt 2152 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _publ_section_references ; Bruker AXS. (2010). APEX2 Bruker AXS, Inc. Madison, Wisconsin, USA. Bruker AXS. (2009). SAINT Bruker AXS, Inc. Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _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^)+(0.0576P)^2^+0.4614P] 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_number_reflns 2598 _refine_ls_number_parameters 194 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.064 _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 0.84845(3) 1.05510(7) 0.78807(3) 0.02653(17) Uani 1 1 d . A . C1 C 0.98559(17) 1.1333(4) 0.57661(12) 0.0387(5) Uani 1 1 d . . . H1A H 1.0416 1.0529 0.5839 0.046 Uiso 1 1 calc R . . H1B H 0.9779 1.2521 0.5418 0.046 Uiso 1 1 calc R . . N1 N 0.94113(11) 0.9656(3) 0.75834(10) 0.0290(4) Uani 1 1 d . . . H1N H 0.9668 0.8593 0.7946 0.043 Uiso 1 1 d R . . O1 O 0.81931(10) 1.2380(2) 0.74055(9) 0.0368(4) Uani 1 1 d . . . C2 C 0.91899(15) 1.0803(3) 0.61455(13) 0.0352(5) Uani 1 1 d . . . H2 H 0.8638 1.1635 0.6061 0.042 Uiso 1 1 calc R . . N2 N 0.76617(10) 0.8779(2) 0.76185(9) 0.0229(3) Uani 1 1 d . . . O2 O 0.87171(10) 1.0716(2) 0.87511(8) 0.0351(4) Uani 1 1 d . . . C3 C 0.92497(13) 0.8951(3) 0.67072(12) 0.0283(4) Uani 1 1 d . A . H3 H 0.9823 0.8153 0.6650 0.034 Uiso 1 1 calc R . . C4 C 0.84180(13) 0.7419(3) 0.64980(11) 0.0258(4) Uani 1 1 d . . . H4 H 0.8604 0.6119 0.6824 0.031 Uiso 1 1 calc R A . C5 C 0.82358(15) 0.6816(3) 0.55910(12) 0.0333(5) Uani 1 1 d . A . H5A H 0.8097 0.8093 0.5253 0.040 Uiso 1 1 calc R . . H5B H 0.8811 0.6179 0.5471 0.040 Uiso 1 1 calc R . . C6 C 0.74220(15) 0.5290(3) 0.53513(12) 0.0347(5) Uani 1 1 d . . . H6A H 0.7301 0.5036 0.4753 0.042 Uiso 1 1 calc R A . H6B H 0.7591 0.3942 0.5634 0.042 Uiso 1 1 calc R . . C7 C 0.65383(14) 0.6147(3) 0.55820(12) 0.0319(5) Uani 1 1 d . A . H7A H 0.6025 0.5111 0.5443 0.038 Uiso 1 1 calc R . . H7B H 0.6338 0.7434 0.5265 0.038 Uiso 1 1 calc R . . C8 C 0.67216(13) 0.6633(3) 0.64976(11) 0.0272(4) Uani 1 1 d . . . H8A H 0.6898 0.5336 0.6815 0.033 Uiso 1 1 calc R A . H8B H 0.6142 0.7186 0.6640 0.033 Uiso 1 1 calc R . . C9 C 0.75097(13) 0.8234(3) 0.67237(11) 0.0243(4) Uani 1 1 d . A . H9 H 0.7314 0.9530 0.6399 0.029 Uiso 1 1 calc R . . C10A C 0.76833(19) 0.7042(4) 0.82238(16) 0.0225(7) Uani 0.656(4) 1 d P A 1 H10A H 0.8137 0.7400 0.8735 0.027 Uiso 0.656(4) 1 calc PR A 1 H10B H 0.7909 0.5757 0.7999 0.027 Uiso 0.656(4) 1 calc PR A 1 C11A C 0.6736(3) 0.6608(7) 0.8427(2) 0.0221(7) Uiso 0.656(4) 1 d P A 1 C12A C 0.6605(3) 0.4696(7) 0.8793(3) 0.0303(10) Uiso 0.656(4) 1 d P A 1 H12A H 0.7101 0.3704 0.8883 0.036 Uiso 0.656(4) 1 calc PR A 1 C13A C 0.5773(3) 0.4210(7) 0.9029(2) 0.0304(11) Uiso 0.656(4) 1 d P A 1 H13A H 0.5693 0.2914 0.9282 0.036 Uiso 0.656(4) 1 calc PR A 1 C14A C 0.5067(3) 0.5682(7) 0.8881(2) 0.0301(9) Uiso 0.656(4) 1 d P A 1 H14A H 0.4491 0.5390 0.9039 0.036 Uiso 0.656(4) 1 calc PR A 1 C15A C 0.5174(3) 0.7594(5) 0.8507(2) 0.0326(8) Uiso 0.656(4) 1 d P A 1 H15A H 0.4674 0.8576 0.8408 0.039 Uiso 0.656(4) 1 calc PR A 1 C16A C 0.6015(3) 0.8044(5) 0.82813(18) 0.0261(7) Uiso 0.656(4) 1 d P A 1 H16A H 0.6095 0.9338 0.8027 0.031 Uiso 0.656(4) 1 calc PR A 1 C10B C 0.6817(4) 0.9384(8) 0.7889(3) 0.0246(14) Uani 0.344(4) 1 d P A 2 H10C H 0.6349 0.9922 0.7415 0.030 Uiso 0.344(4) 1 calc PR A 2 H10D H 0.6968 1.0521 0.8297 0.030 Uiso 0.344(4) 1 calc PR A 2 C11B C 0.6395(5) 0.7557(11) 0.8269(3) 0.0222(13) Uiso 0.344(4) 1 d PD A 2 C12B C 0.5448(6) 0.7721(10) 0.8308(4) 0.0370(18) Uiso 0.344(4) 1 d PD A 2 H12B H 0.5101 0.8899 0.8066 0.044 Uiso 0.344(4) 1 calc PR A 2 C13B C 0.4997(4) 0.6233(12) 0.8686(4) 0.0304(18) Uiso 0.344(4) 1 d PD A 2 H13B H 0.4359 0.6362 0.8727 0.036 Uiso 0.344(4) 1 calc PR A 2 C14B C 0.5548(5) 0.4543(12) 0.9000(4) 0.032(2) Uiso 0.344(4) 1 d PD A 2 H14B H 0.5265 0.3467 0.9256 0.038 Uiso 0.344(4) 1 calc PR A 2 C15B C 0.6501(5) 0.4313(13) 0.8965(5) 0.041(3) Uiso 0.344(4) 1 d PD A 2 H15B H 0.6849 0.3121 0.9192 0.049 Uiso 0.344(4) 1 calc PR A 2 C16B C 0.6913(4) 0.5864(12) 0.8592(4) 0.0268(16) Uiso 0.344(4) 1 d PD A 2 H16B H 0.7555 0.5758 0.8560 0.032 Uiso 0.344(4) 1 calc PR A 2 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 0.0300(3) 0.0228(3) 0.0283(3) -0.00150(17) 0.00944(19) -0.00279(18) C1 0.0524(14) 0.0367(12) 0.0308(11) -0.0039(9) 0.0174(10) -0.0100(10) N1 0.0271(9) 0.0296(9) 0.0306(9) 0.0040(7) 0.0069(7) -0.0015(7) O1 0.0459(9) 0.0233(8) 0.0457(9) 0.0039(6) 0.0197(7) 0.0048(6) C2 0.0412(12) 0.0317(12) 0.0362(12) 0.0044(8) 0.0161(9) 0.0046(9) N2 0.0255(8) 0.0220(8) 0.0221(8) 0.0005(6) 0.0072(6) -0.0003(6) O2 0.0365(8) 0.0381(9) 0.0317(8) -0.0068(6) 0.0092(6) -0.0097(6) C3 0.0275(10) 0.0285(11) 0.0317(11) 0.0030(8) 0.0128(8) 0.0045(8) C4 0.0272(10) 0.0253(10) 0.0259(10) 0.0028(7) 0.0077(8) 0.0041(7) C5 0.0368(11) 0.0388(12) 0.0265(10) 0.0006(8) 0.0119(8) 0.0075(9) C6 0.0421(12) 0.0368(12) 0.0242(10) -0.0034(8) 0.0044(9) 0.0059(9) C7 0.0332(11) 0.0348(11) 0.0252(10) 0.0002(8) 0.0006(8) 0.0019(8) C8 0.0265(10) 0.0286(11) 0.0256(10) 0.0020(7) 0.0031(8) 0.0016(8) C9 0.0268(10) 0.0245(10) 0.0217(9) 0.0021(7) 0.0056(7) 0.0042(7) C10A 0.0226(15) 0.0242(15) 0.0205(14) 0.0012(11) 0.0044(11) 0.0010(11) C10B 0.030(3) 0.023(3) 0.020(3) -0.001(2) 0.003(2) 0.002(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 O2 1.4236(14) . ? S1 O1 1.4286(15) . ? S1 N1 1.6368(16) . ? S1 N2 1.6419(15) . ? C1 C2 1.310(3) . ? C1 H1A 0.9500 . ? C1 H1B 0.9500 . ? N1 C3 1.500(2) . ? N1 H1N 0.9348 . ? C2 C3 1.504(3) . ? C2 H2 0.9500 . ? N2 C10B 1.450(6) . ? N2 C10A 1.499(3) . ? N2 C9 1.503(2) . ? C3 C4 1.541(3) . ? C3 H3 1.0000 . ? C4 C5 1.530(3) . ? C4 C9 1.541(3) . ? C4 H4 1.0000 . ? C5 C6 1.524(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.522(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.526(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.526(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9 1.0000 . ? C10A C11A 1.514(4) . ? C10A H10A 0.9900 . ? C10A H10B 0.9900 . ? C11A C16A 1.379(5) . ? C11A C12A 1.400(6) . ? C12A C13A 1.386(6) . ? C12A H12A 0.9500 . ? C13A C14A 1.379(6) . ? C13A H13A 0.9500 . ? C14A C15A 1.399(5) . ? C14A H14A 0.9500 . ? C15A C16A 1.385(5) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C10B C11B 1.522(8) . ? C10B H10C 0.9900 . ? C10B H10D 0.9900 . ? C11B C16B 1.366(7) . ? C11B C12B 1.398(7) . ? C12B C13B 1.383(8) . ? C12B H12B 0.9500 . ? C13B C14B 1.383(8) . ? C13B H13B 0.9500 . ? C14B C15B 1.410(8) . ? C14B H14B 0.9500 . ? C15B C16B 1.375(8) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? 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 O2 S1 O1 118.94(9) . . ? O2 S1 N1 107.52(8) . . ? O1 S1 N1 106.67(8) . . ? O2 S1 N2 109.06(8) . . ? O1 S1 N2 107.76(9) . . ? N1 S1 N2 106.19(8) . . ? C2 C1 H1A 120.0 . . ? C2 C1 H1B 120.0 . . ? H1A C1 H1B 120.0 . . ? C3 N1 S1 115.52(12) . . ? C3 N1 H1N 111.7 . . ? S1 N1 H1N 107.6 . . ? C1 C2 C3 123.7(2) . . ? C1 C2 H2 118.2 . . ? C3 C2 H2 118.2 . . ? C10B N2 C10A 83.5(2) . . ? C10B N2 C9 114.5(2) . . ? C10A N2 C9 118.31(16) . . ? C10B N2 S1 110.6(2) . . ? C10A N2 S1 115.08(14) . . ? C9 N2 S1 111.82(11) . . ? N1 C3 C2 110.23(16) . . ? N1 C3 C4 111.53(15) . . ? C2 C3 C4 114.99(16) . . ? N1 C3 H3 106.5 . . ? C2 C3 H3 106.5 . . ? C4 C3 H3 106.5 . . ? C5 C4 C3 110.43(15) . . ? C5 C4 C9 110.40(15) . . ? C3 C4 C9 113.74(15) . . ? C5 C4 H4 107.3 . . ? C3 C4 H4 107.3 . . ? C9 C4 H4 107.3 . . ? C6 C5 C4 112.63(16) . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 110.76(17) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C6 C7 C8 110.36(16) . . ? C6 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? C6 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C7 C8 C9 110.38(15) . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N2 C9 C8 110.31(14) . . ? N2 C9 C4 111.54(14) . . ? C8 C9 C4 110.54(15) . . ? N2 C9 H9 108.1 . . ? C8 C9 H9 108.1 . . ? C4 C9 H9 108.1 . . ? N2 C10A C11A 113.4(3) . . ? N2 C10A H10A 108.9 . . ? C11A C10A H10A 108.9 . . ? N2 C10A H10B 108.9 . . ? C11A C10A H10B 108.9 . . ? H10A C10A H10B 107.7 . . ? C16A C11A C12A 119.5(3) . . ? C16A C11A C10A 122.3(4) . . ? C12A C11A C10A 118.2(4) . . ? C13A C12A C11A 121.9(4) . . ? C13A C12A H12A 119.1 . . ? C11A C12A H12A 119.1 . . ? C14A C13A C12A 117.3(4) . . ? C14A C13A H13A 121.3 . . ? C12A C13A H13A 121.3 . . ? C13A C14A C15A 122.0(3) . . ? C13A C14A H14A 119.0 . . ? C15A C14A H14A 119.0 . . ? C16A C15A C14A 119.5(3) . . ? C16A C15A H15A 120.3 . . ? C14A C15A H15A 120.3 . . ? C11A C16A C15A 119.8(3) . . ? C11A C16A H16A 120.1 . . ? C15A C16A H16A 120.1 . . ? N2 C10B C11B 111.6(5) . . ? N2 C10B H10C 109.3 . . ? C11B C10B H10C 109.3 . . ? N2 C10B H10D 109.3 . . ? C11B C10B H10D 109.3 . . ? H10C C10B H10D 108.0 . . ? C16B C11B C12B 120.6(5) . . ? C16B C11B C10B 122.6(6) . . ? C12B C11B C10B 116.8(7) . . ? C13B C12B C11B 122.5(6) . . ? C13B C12B H12B 118.8 . . ? C11B C12B H12B 118.8 . . ? C14B C13B C12B 114.8(6) . . ? C14B C13B H13B 122.6 . . ? C12B C13B H13B 122.6 . . ? C13B C14B C15B 124.3(7) . . ? C13B C14B H14B 117.9 . . ? C15B C14B H14B 117.9 . . ? C16B C15B C14B 118.0(7) . . ? C16B C15B H15B 121.0 . . ? C14B C15B H15B 121.0 . . ? C11B C16B C15B 119.8(6) . . ? C11B C16B H16B 120.1 . . ? C15B C16B H16B 120.1 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 65.97 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.240 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.045