# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 N O3 S' _chemical_formula_sum 'C16 H17 N O3 S' _chemical_formula_weight 303.37 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 15.908(4) _cell_length_b 5.9035(14) _cell_length_c 16.411(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.783(4) _cell_angle_gamma 90.00 _cell_volume 1503.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2954 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.0 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details ? _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9166 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 26.05 _reflns_number_total 2954 _reflns_number_gt 2221 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0554P)^2^+0.1726P] 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 2954 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 C1 C 0.16068(13) -0.0913(3) 0.71505(12) 0.0433(5) Uani 1 1 d . . . C2 C 0.10184(15) -0.2640(4) 0.71455(14) 0.0571(6) Uani 1 1 d . . . H2 H 0.1198 -0.3973 0.7433 0.069 Uiso 1 1 calc R . . C3 C 0.01756(16) -0.2425(4) 0.67250(16) 0.0662(7) Uani 1 1 d . . . H3 H -0.0215 -0.3585 0.6745 0.079 Uiso 1 1 calc R . . C4 C -0.00906(15) -0.0498(4) 0.62751(15) 0.0658(7) Uani 1 1 d . . . H4 H -0.0658 -0.0368 0.5976 0.079 Uiso 1 1 calc R . . C5 C 0.04841(15) 0.1250(4) 0.62656(15) 0.0639(6) Uani 1 1 d . . . H5 H 0.0305 0.2552 0.5957 0.077 Uiso 1 1 calc R . . C6 C 0.13257(14) 0.1063(4) 0.67149(13) 0.0537(6) Uani 1 1 d . . . H6 H 0.1706 0.2266 0.6726 0.064 Uiso 1 1 calc R . . C7 C 0.25372(14) -0.1286(3) 0.75511(12) 0.0448(5) Uani 1 1 d . . . C8 C 0.30047(12) 0.0365(3) 0.81369(11) 0.0387(4) Uani 1 1 d . . . C9 C 0.26855(13) 0.2238(3) 0.85119(12) 0.0419(5) Uani 1 1 d . . . H9 H 0.2111 0.2673 0.8428 0.050 Uiso 1 1 calc R . . C10 C 0.33683(13) 0.3297(3) 0.90180(11) 0.0400(5) Uani 1 1 d . . . C11 C 0.38990(12) 0.0337(3) 0.84358(11) 0.0390(4) Uani 1 1 d . . . C12 C 0.56303(12) -0.0622(4) 0.87591(13) 0.0472(5) Uani 1 1 d . . . H12A H 0.5725 0.0936 0.8614 0.057 Uiso 1 1 calc R . . H12B H 0.5643 -0.0693 0.9352 0.057 Uiso 1 1 calc R . . C13 C 0.63245(14) -0.2134(4) 0.85529(14) 0.0553(6) Uani 1 1 d . . . H13A H 0.6879 -0.1639 0.8861 0.083 Uiso 1 1 calc R . . H13B H 0.6306 -0.2052 0.7965 0.083 Uiso 1 1 calc R . . H13C H 0.6228 -0.3669 0.8702 0.083 Uiso 1 1 calc R . . C14 C 0.34060(13) 0.5249(3) 0.95626(12) 0.0408(5) Uani 1 1 d . . . C15 C 0.25742(14) 0.7986(3) 1.00801(13) 0.0486(5) Uani 1 1 d . . . H15A H 0.2917 0.9213 0.9930 0.058 Uiso 1 1 calc R . . H15B H 0.2800 0.7604 1.0662 0.058 Uiso 1 1 calc R . . C16 C 0.16500(15) 0.8689(4) 0.99483(17) 0.0691(7) Uani 1 1 d . . . H16A H 0.1606 0.9984 1.0290 0.104 Uiso 1 1 calc R . . H16B H 0.1318 0.7464 1.0099 0.104 Uiso 1 1 calc R . . H16C H 0.1434 0.9069 0.9371 0.104 Uiso 1 1 calc R . . N1 N 0.41080(12) 0.2121(3) 0.89626(10) 0.0413(4) Uani 1 1 d . . . O1 O 0.28868(10) -0.2995(3) 0.73619(10) 0.0665(5) Uani 1 1 d . . . O2 O 0.40619(9) 0.6063(2) 0.99797(9) 0.0517(4) Uani 1 1 d . . . O3 O 0.26099(8) 0.6032(2) 0.95555(8) 0.0492(4) Uani 1 1 d . . . S1 S 0.46059(3) -0.16049(9) 0.81662(3) 0.04580(18) Uani 1 1 d . . . HN1 H 0.4587(14) 0.257(4) 0.9189(13) 0.047(7) Uiso 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 0.0461(12) 0.0422(11) 0.0411(11) -0.0049(9) 0.0087(9) 0.0000(9) C2 0.0589(15) 0.0446(12) 0.0648(15) 0.0020(11) 0.0071(12) -0.0027(11) C3 0.0536(15) 0.0595(14) 0.0820(17) -0.0063(13) 0.0075(13) -0.0134(12) C4 0.0466(14) 0.0749(17) 0.0695(16) -0.0078(13) -0.0008(12) 0.0024(13) C5 0.0551(15) 0.0600(15) 0.0712(16) 0.0125(12) 0.0022(12) 0.0074(12) C6 0.0487(13) 0.0499(13) 0.0608(14) 0.0051(10) 0.0084(11) -0.0017(10) C7 0.0494(12) 0.0412(11) 0.0434(11) 0.0004(9) 0.0093(9) 0.0025(9) C8 0.0400(11) 0.0391(10) 0.0367(10) 0.0032(8) 0.0078(8) 0.0013(8) C9 0.0425(11) 0.0414(11) 0.0419(11) 0.0025(9) 0.0094(9) 0.0041(9) C10 0.0429(11) 0.0387(10) 0.0400(10) 0.0013(8) 0.0126(9) 0.0041(9) C11 0.0463(11) 0.0374(10) 0.0338(10) 0.0014(8) 0.0102(8) 0.0011(9) C12 0.0452(12) 0.0520(12) 0.0433(11) -0.0078(10) 0.0078(9) 0.0046(10) C13 0.0481(13) 0.0558(13) 0.0620(14) -0.0144(11) 0.0120(11) 0.0023(10) C14 0.0435(12) 0.0397(11) 0.0398(10) 0.0019(8) 0.0106(9) 0.0023(9) C15 0.0495(12) 0.0459(12) 0.0491(12) -0.0100(9) 0.0081(10) 0.0049(10) C16 0.0512(14) 0.0710(16) 0.0837(17) -0.0245(14) 0.0122(13) 0.0104(12) N1 0.0403(10) 0.0432(10) 0.0397(9) -0.0013(7) 0.0072(8) 0.0004(8) O1 0.0595(10) 0.0540(9) 0.0792(11) -0.0217(8) 0.0009(8) 0.0119(8) O2 0.0436(9) 0.0554(9) 0.0540(9) -0.0125(7) 0.0064(7) 0.0015(7) O3 0.0422(8) 0.0483(8) 0.0555(9) -0.0152(7) 0.0073(7) 0.0031(7) S1 0.0444(3) 0.0448(3) 0.0468(3) -0.0077(2) 0.0072(2) 0.0046(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.383(3) . ? C1 C6 1.389(3) . ? C1 C7 1.497(3) . ? C2 C3 1.371(3) . ? C2 H2 0.9300 . ? C3 C4 1.371(4) . ? C3 H3 0.9300 . ? C4 C5 1.381(3) . ? C4 H4 0.9300 . ? C5 C6 1.383(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.225(2) . ? C7 C8 1.453(3) . ? C8 C11 1.399(3) . ? C8 C9 1.414(3) . ? C9 C10 1.364(3) . ? C9 H9 0.9300 . ? C10 N1 1.386(3) . ? C10 C14 1.451(3) . ? C11 N1 1.357(2) . ? C11 S1 1.7306(19) . ? C12 C13 1.515(3) . ? C12 S1 1.799(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O2 1.213(2) . ? C14 O3 1.346(2) . ? C15 O3 1.448(2) . ? C15 C16 1.496(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? N1 HN1 0.82(2) . ? 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 118.4(2) . . ? C2 C1 C7 119.77(19) . . ? C6 C1 C7 121.59(18) . . ? C3 C2 C1 121.3(2) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.0(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.3(2) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? O1 C7 C8 121.72(19) . . ? O1 C7 C1 118.03(18) . . ? C8 C7 C1 120.24(17) . . ? C11 C8 C9 106.98(17) . . ? C11 C8 C7 123.79(17) . . ? C9 C8 C7 129.23(18) . . ? C10 C9 C8 108.01(18) . . ? C10 C9 H9 126.0 . . ? C8 C9 H9 126.0 . . ? C9 C10 N1 107.70(17) . . ? C9 C10 C14 131.11(19) . . ? N1 C10 C14 121.18(18) . . ? N1 C11 C8 107.53(17) . . ? N1 C11 S1 126.57(15) . . ? C8 C11 S1 125.89(15) . . ? C13 C12 S1 107.87(14) . . ? C13 C12 H12A 110.1 . . ? S1 C12 H12A 110.1 . . ? C13 C12 H12B 110.1 . . ? S1 C12 H12B 110.1 . . ? H12A C12 H12B 108.4 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 O3 123.98(18) . . ? O2 C14 C10 125.10(18) . . ? O3 C14 C10 110.91(17) . . ? O3 C15 C16 107.54(17) . . ? O3 C15 H15A 110.2 . . ? C16 C15 H15A 110.2 . . ? O3 C15 H15B 110.2 . . ? C16 C15 H15B 110.2 . . ? H15A C15 H15B 108.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 N1 C10 109.78(17) . . ? C11 N1 HN1 128.1(15) . . ? C10 N1 HN1 121.9(16) . . ? C14 O3 C15 115.42(15) . . ? C11 S1 C12 102.12(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 -0.2(3) . . . . ? C7 C1 C2 C3 -174.5(2) . . . . ? C1 C2 C3 C4 2.2(4) . . . . ? C2 C3 C4 C5 -1.9(4) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C1 2.6(4) . . . . ? C2 C1 C6 C5 -2.2(3) . . . . ? C7 C1 C6 C5 172.0(2) . . . . ? C2 C1 C7 O1 49.5(3) . . . . ? C6 C1 C7 O1 -124.6(2) . . . . ? C2 C1 C7 C8 -131.3(2) . . . . ? C6 C1 C7 C8 54.5(3) . . . . ? O1 C7 C8 C11 9.7(3) . . . . ? C1 C7 C8 C11 -169.46(17) . . . . ? O1 C7 C8 C9 -170.3(2) . . . . ? C1 C7 C8 C9 10.6(3) . . . . ? C11 C8 C9 C10 0.1(2) . . . . ? C7 C8 C9 C10 -179.99(19) . . . . ? C8 C9 C10 N1 0.2(2) . . . . ? C8 C9 C10 C14 -178.07(19) . . . . ? C9 C8 C11 N1 -0.3(2) . . . . ? C7 C8 C11 N1 179.71(17) . . . . ? C9 C8 C11 S1 -179.49(14) . . . . ? C7 C8 C11 S1 0.6(3) . . . . ? C9 C10 C14 O2 -179.0(2) . . . . ? N1 C10 C14 O2 2.9(3) . . . . ? C9 C10 C14 O3 1.9(3) . . . . ? N1 C10 C14 O3 -176.18(16) . . . . ? C8 C11 N1 C10 0.5(2) . . . . ? S1 C11 N1 C10 179.63(14) . . . . ? C9 C10 N1 C11 -0.5(2) . . . . ? C14 C10 N1 C11 178.05(17) . . . . ? O2 C14 O3 C15 0.9(3) . . . . ? C10 C14 O3 C15 -179.98(16) . . . . ? C16 C15 O3 C14 176.49(18) . . . . ? N1 C11 S1 C12 0.30(19) . . . . ? C8 C11 S1 C12 179.28(17) . . . . ? C13 C12 S1 C11 -177.70(15) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.193 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 949218' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H23 N O4 S2' _chemical_formula_sum 'C19 H23 N O4 S2' _chemical_formula_weight 393.50 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6230(6) _cell_length_b 10.8704(7) _cell_length_c 10.8806(7) _cell_angle_alpha 81.7010(10) _cell_angle_beta 86.1890(10) _cell_angle_gamma 78.4900(10) _cell_volume 988.18(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3829 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 26.0 _exptl_crystal_description bulk _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.293 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 0.943 _exptl_absorpt_process_details ? _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5443 _diffrn_reflns_av_R_equivalents 0.0115 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.05 _reflns_number_total 3829 _reflns_number_gt 3270 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0599P)^2^+0.4217P] 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 3829 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1174 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C1 C 0.1414(2) 0.16789(19) 0.76421(18) 0.0387(4) Uani 1 1 d . . . C2 C 0.2383(3) 0.2570(2) 0.7494(2) 0.0465(5) Uani 1 1 d . . . H2 H 0.1942 0.3418 0.7535 0.056 Uiso 1 1 calc R . . C3 C 0.4003(3) 0.2211(3) 0.7286(2) 0.0608(6) Uani 1 1 d . . . H3 H 0.4644 0.2814 0.7194 0.073 Uiso 1 1 calc R . . C4 C 0.4658(3) 0.0967(3) 0.7216(3) 0.0737(8) Uani 1 1 d . . . H4 H 0.5746 0.0722 0.7082 0.088 Uiso 1 1 calc R . . C5 C 0.3704(3) 0.0081(3) 0.7344(3) 0.0783(9) Uani 1 1 d . . . H5 H 0.4151 -0.0762 0.7286 0.094 Uiso 1 1 calc R . . C6 C 0.2086(3) 0.0425(2) 0.7559(3) 0.0582(6) Uani 1 1 d . . . H6 H 0.1453 -0.0184 0.7647 0.070 Uiso 1 1 calc R . . C7 C -0.0372(2) 0.21210(17) 0.78480(17) 0.0358(4) Uani 1 1 d . . . C8 C -0.1082(2) 0.31312(17) 0.67875(17) 0.0345(4) Uani 1 1 d . . . C9 C -0.1716(2) 0.42716(19) 0.73096(18) 0.0389(4) Uani 1 1 d . . . H9 H -0.2219 0.5021 0.6859 0.047 Uiso 1 1 calc R . . C10 C -0.1487(2) 0.41180(19) 0.85380(18) 0.0390(4) Uani 1 1 d . . . C11 C -0.0286(3) 0.2326(2) 1.00989(19) 0.0468(5) Uani 1 1 d . . . H11 H -0.0516 0.2816 1.0745 0.056 Uiso 1 1 calc R . . C12 C -0.2029(3) 0.5079(2) 0.93822(19) 0.0434(5) Uani 1 1 d . . . C13 C -0.3523(3) 0.7181(2) 0.9443(2) 0.0594(6) Uani 1 1 d . . . H13A H -0.3506 0.7990 0.8937 0.071 Uiso 1 1 calc R . . H13B H -0.2931 0.7145 1.0179 0.071 Uiso 1 1 calc R . . C14 C -0.5186(4) 0.7075(3) 0.9813(3) 0.0848(9) Uani 1 1 d . . . H14A H -0.5660 0.7757 1.0270 0.127 Uiso 1 1 calc R . . H14B H -0.5199 0.6280 1.0326 0.127 Uiso 1 1 calc R . . H14C H -0.5772 0.7120 0.9083 0.127 Uiso 1 1 calc R . . C15 C -0.1073(2) 0.29802(17) 0.55728(18) 0.0359(4) Uani 1 1 d . . . C16 C -0.2836(3) 0.3822(2) 0.3419(2) 0.0577(6) Uani 1 1 d . . . H16A H -0.3036 0.4469 0.2703 0.069 Uiso 1 1 calc R . . H16B H -0.2249 0.3056 0.3123 0.069 Uiso 1 1 calc R . . C17 C -0.4359(4) 0.3575(4) 0.3973(3) 0.0925(11) Uani 1 1 d . . . H17A H -0.4934 0.3312 0.3363 0.139 Uiso 1 1 calc R . . H17B H -0.4963 0.4333 0.4250 0.139 Uiso 1 1 calc R . . H17C H -0.4176 0.2917 0.4667 0.139 Uiso 1 1 calc R . . C18 C 0.0833(3) 0.1737(2) 0.3771(2) 0.0542(6) Uani 1 1 d . . . H18A H 0.0990 0.1021 0.3307 0.065 Uiso 1 1 calc R . . H18B H 0.0374 0.2487 0.3222 0.065 Uiso 1 1 calc R . . C19 C 0.2397(4) 0.1894(3) 0.4159(3) 0.0792(9) Uani 1 1 d . . . H19A H 0.3076 0.2026 0.3436 0.119 Uiso 1 1 calc R . . H19B H 0.2870 0.1147 0.4687 0.119 Uiso 1 1 calc R . . H19C H 0.2253 0.2613 0.4604 0.119 Uiso 1 1 calc R . . N1 N -0.0674(2) 0.28737(15) 0.89312(14) 0.0385(4) Uani 1 1 d . . . O1 O -0.1833(2) 0.49344(17) 1.04774(15) 0.0634(5) Uani 1 1 d . . . O2 O -0.2779(2) 0.61563(15) 0.87428(15) 0.0594(4) Uani 1 1 d . . . O3 O -0.12395(17) 0.11482(13) 0.80231(13) 0.0437(3) Uani 1 1 d . . . H3A H -0.0932 0.0648 0.8636 0.065 Uiso 1 1 calc R . . O4 O 0.0352(2) 0.12186(15) 1.03371(15) 0.0582(4) Uani 1 1 d . . . S1 S -0.16166(7) 0.43340(5) 0.44649(5) 0.04584(17) Uani 1 1 d . . . S2 S -0.05489(7) 0.14825(5) 0.50746(5) 0.04627(17) 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 0.0430(11) 0.0399(10) 0.0311(10) -0.0003(8) -0.0039(8) -0.0050(8) C2 0.0490(12) 0.0489(12) 0.0420(11) -0.0056(9) 0.0003(9) -0.0118(10) C3 0.0501(14) 0.0834(19) 0.0534(14) -0.0093(13) 0.0027(11) -0.0250(13) C4 0.0432(14) 0.097(2) 0.0741(19) -0.0112(17) -0.0004(13) 0.0017(14) C5 0.0596(17) 0.0616(17) 0.102(2) -0.0083(16) -0.0007(16) 0.0140(14) C6 0.0531(14) 0.0433(12) 0.0728(17) -0.0015(11) -0.0036(12) -0.0003(10) C7 0.0440(11) 0.0328(9) 0.0296(9) -0.0007(7) -0.0022(8) -0.0070(8) C8 0.0382(10) 0.0314(9) 0.0330(9) -0.0021(7) -0.0024(8) -0.0057(7) C9 0.0433(11) 0.0359(10) 0.0354(10) -0.0046(8) -0.0032(8) -0.0027(8) C10 0.0409(11) 0.0401(10) 0.0348(10) -0.0047(8) 0.0005(8) -0.0057(8) C11 0.0568(13) 0.0505(13) 0.0327(10) 0.0022(9) -0.0031(9) -0.0147(10) C12 0.0457(12) 0.0484(12) 0.0367(11) -0.0091(9) 0.0026(9) -0.0095(9) C13 0.0689(16) 0.0509(13) 0.0581(15) -0.0229(11) -0.0019(12) 0.0003(12) C14 0.0654(18) 0.099(2) 0.096(2) -0.040(2) 0.0089(16) -0.0124(16) C15 0.0423(10) 0.0317(9) 0.0332(9) -0.0034(7) -0.0024(8) -0.0061(8) C16 0.0707(16) 0.0611(15) 0.0413(12) -0.0063(11) -0.0152(11) -0.0085(12) C17 0.072(2) 0.128(3) 0.089(2) -0.044(2) -0.0028(17) -0.025(2) C18 0.0702(16) 0.0497(13) 0.0406(12) -0.0119(10) 0.0063(11) -0.0050(11) C19 0.0722(19) 0.106(2) 0.0603(17) -0.0157(16) 0.0126(14) -0.0222(17) N1 0.0459(9) 0.0395(9) 0.0290(8) -0.0024(7) -0.0005(7) -0.0075(7) O1 0.0866(13) 0.0652(11) 0.0355(9) -0.0139(8) -0.0012(8) -0.0032(9) O2 0.0798(12) 0.0495(9) 0.0436(9) -0.0173(7) -0.0056(8) 0.0089(8) O3 0.0501(8) 0.0391(7) 0.0422(8) 0.0042(6) -0.0059(6) -0.0150(6) O4 0.0759(11) 0.0507(10) 0.0441(9) 0.0113(7) -0.0098(8) -0.0132(8) S1 0.0647(4) 0.0376(3) 0.0341(3) 0.0006(2) -0.0111(2) -0.0080(2) S2 0.0627(4) 0.0339(3) 0.0424(3) -0.0100(2) 0.0035(2) -0.0079(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.384(3) . ? C1 C2 1.387(3) . ? C1 C7 1.530(3) . ? C2 C3 1.386(3) . ? C2 H2 0.9300 . ? C3 C4 1.369(4) . ? C3 H3 0.9300 . ? C4 C5 1.374(4) . ? C4 H4 0.9300 . ? C5 C6 1.384(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O3 1.398(2) . ? C7 N1 1.510(2) . ? C7 C8 1.540(3) . ? C8 C15 1.354(3) . ? C8 C9 1.432(3) . ? C9 C10 1.346(3) . ? C9 H9 0.9300 . ? C10 N1 1.414(3) . ? C10 C12 1.476(3) . ? C11 O4 1.218(3) . ? C11 N1 1.356(3) . ? C11 H11 0.9300 . ? C12 O1 1.198(3) . ? C12 O2 1.340(3) . ? C13 O2 1.459(3) . ? C13 C14 1.486(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 S2 1.7542(19) . ? C15 S1 1.7681(19) . ? C16 C17 1.466(4) . ? C16 S1 1.813(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.488(4) . ? C18 S2 1.816(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? O3 H3A 0.8200 . ? 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 118.9(2) . . ? C6 C1 C7 122.13(19) . . ? C2 C1 C7 118.91(18) . . ? C3 C2 C1 120.7(2) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 119.8(2) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O3 C7 N1 110.31(15) . . ? O3 C7 C1 114.54(16) . . ? N1 C7 C1 109.36(15) . . ? O3 C7 C8 109.01(15) . . ? N1 C7 C8 100.82(14) . . ? C1 C7 C8 111.95(15) . . ? C15 C8 C9 126.03(17) . . ? C15 C8 C7 126.22(17) . . ? C9 C8 C7 107.73(16) . . ? C10 C9 C8 111.18(18) . . ? C10 C9 H9 124.4 . . ? C8 C9 H9 124.4 . . ? C9 C10 N1 110.18(17) . . ? C9 C10 C12 126.00(19) . . ? N1 C10 C12 123.80(18) . . ? O4 C11 N1 122.7(2) . . ? O4 C11 H11 118.6 . . ? N1 C11 H11 118.6 . . ? O1 C12 O2 124.3(2) . . ? O1 C12 C10 125.8(2) . . ? O2 C12 C10 109.96(17) . . ? O2 C13 C14 110.4(2) . . ? O2 C13 H13A 109.6 . . ? C14 C13 H13A 109.6 . . ? O2 C13 H13B 109.6 . . ? C14 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 S2 121.84(15) . . ? C8 C15 S1 118.81(14) . . ? S2 C15 S1 119.36(11) . . ? C17 C16 S1 114.45(19) . . ? C17 C16 H16A 108.6 . . ? S1 C16 H16A 108.6 . . ? C17 C16 H16B 108.6 . . ? S1 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 S2 113.05(18) . . ? C19 C18 H18A 109.0 . . ? S2 C18 H18A 109.0 . . ? C19 C18 H18B 109.0 . . ? S2 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C11 N1 C10 128.51(18) . . ? C11 N1 C7 121.24(17) . . ? C10 N1 C7 110.07(15) . . ? C12 O2 C13 117.74(18) . . ? C7 O3 H3A 109.5 . . ? C15 S1 C16 103.79(11) . . ? C15 S2 C18 103.09(10) . . ? 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 -1.0(3) . . . . ? C7 C1 C2 C3 -179.0(2) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 -0.8(5) . . . . ? C4 C5 C6 C1 0.2(5) . . . . ? C2 C1 C6 C5 0.7(4) . . . . ? C7 C1 C6 C5 178.5(2) . . . . ? C6 C1 C7 O3 3.9(3) . . . . ? C2 C1 C7 O3 -178.21(17) . . . . ? C6 C1 C7 N1 128.3(2) . . . . ? C2 C1 C7 N1 -53.8(2) . . . . ? C6 C1 C7 C8 -120.8(2) . . . . ? C2 C1 C7 C8 57.0(2) . . . . ? O3 C7 C8 C15 -66.9(2) . . . . ? N1 C7 C8 C15 177.02(19) . . . . ? C1 C7 C8 C15 60.9(3) . . . . ? O3 C7 C8 C9 114.71(17) . . . . ? N1 C7 C8 C9 -1.36(19) . . . . ? C1 C7 C8 C9 -117.52(18) . . . . ? C15 C8 C9 C10 -177.8(2) . . . . ? C7 C8 C9 C10 0.6(2) . . . . ? C8 C9 C10 N1 0.5(2) . . . . ? C8 C9 C10 C12 -177.89(19) . . . . ? C9 C10 C12 O1 179.4(2) . . . . ? N1 C10 C12 O1 1.2(4) . . . . ? C9 C10 C12 O2 -0.9(3) . . . . ? N1 C10 C12 O2 -179.13(18) . . . . ? C9 C8 C15 S2 -169.84(16) . . . . ? C7 C8 C15 S2 12.1(3) . . . . ? C9 C8 C15 S1 9.8(3) . . . . ? C7 C8 C15 S1 -168.26(15) . . . . ? O4 C11 N1 C10 176.3(2) . . . . ? O4 C11 N1 C7 1.7(3) . . . . ? C9 C10 N1 C11 -176.6(2) . . . . ? C12 C10 N1 C11 1.9(3) . . . . ? C9 C10 N1 C7 -1.5(2) . . . . ? C12 C10 N1 C7 176.97(18) . . . . ? O3 C7 N1 C11 62.1(2) . . . . ? C1 C7 N1 C11 -64.7(2) . . . . ? C8 C7 N1 C11 177.20(18) . . . . ? O3 C7 N1 C10 -113.40(17) . . . . ? C1 C7 N1 C10 119.78(17) . . . . ? C8 C7 N1 C10 1.71(19) . . . . ? O1 C12 O2 C13 -5.6(3) . . . . ? C10 C12 O2 C13 174.72(19) . . . . ? C14 C13 O2 C12 -89.9(3) . . . . ? C8 C15 S1 C16 -138.46(18) . . . . ? S2 C15 S1 C16 41.22(16) . . . . ? C17 C16 S1 C15 67.9(2) . . . . ? C8 C15 S2 C18 -132.71(18) . . . . ? S1 C15 S2 C18 47.62(15) . . . . ? C19 C18 S2 C15 72.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.419 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 949219' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 N O3 S' _chemical_formula_sum 'C16 H17 N O3 S' _chemical_formula_weight 303.37 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.094(2) _cell_length_b 9.747(3) _cell_length_c 10.514(3) _cell_angle_alpha 76.657(5) _cell_angle_beta 81.203(6) _cell_angle_gamma 78.138(5) _cell_volume 785.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3015 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 26.0 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details ? _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4281 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 26.05 _reflns_number_total 3015 _reflns_number_gt 2136 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0742P)^2^+0.3726P] 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 3015 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0633 _refine_ls_wR_factor_ref 0.1675 _refine_ls_wR_factor_gt 0.1476 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C1 C 0.9060(3) 0.3219(3) -0.2307(3) 0.0491(7) Uani 1 1 d . . . C2 C 0.8779(4) 0.1997(3) -0.1387(3) 0.0558(7) Uani 1 1 d . . . H2 H 0.8562 0.2036 -0.0500 0.067 Uiso 1 1 calc R . . C3 C 0.8817(4) 0.0729(3) -0.1760(4) 0.0669(9) Uani 1 1 d . . . H3 H 0.8633 -0.0082 -0.1127 0.080 Uiso 1 1 calc R . . C4 C 0.9126(5) 0.0657(4) -0.3063(4) 0.0768(10) Uani 1 1 d . . . H4 H 0.9152 -0.0200 -0.3319 0.092 Uiso 1 1 calc R . . C5 C 0.9396(5) 0.1861(4) -0.3988(4) 0.0829(11) Uani 1 1 d . . . H5 H 0.9596 0.1818 -0.4874 0.099 Uiso 1 1 calc R . . C6 C 0.9375(5) 0.3131(4) -0.3618(3) 0.0701(9) Uani 1 1 d . . . H6 H 0.9575 0.3935 -0.4255 0.084 Uiso 1 1 calc R . . C7 C 0.8964(3) 0.4569(3) -0.1867(3) 0.0467(6) Uani 1 1 d . . . C8 C 1.0058(3) 0.5566(3) -0.2078(3) 0.0477(7) Uani 1 1 d . . . C9 C 0.9310(3) 0.6585(3) -0.1311(3) 0.0492(7) Uani 1 1 d . . . H9 H 0.9758 0.7370 -0.1250 0.059 Uiso 1 1 calc R . . C10 C 0.7812(3) 0.6223(3) -0.0673(3) 0.0478(7) Uani 1 1 d . . . C11 C 0.6521(4) 0.6853(3) 0.0249(3) 0.0537(7) Uani 1 1 d . . . C12 C 0.5794(5) 0.8515(4) 0.1643(4) 0.0791(11) Uani 1 1 d . . . H12A H 0.4670 0.8831 0.1356 0.095 Uiso 1 1 calc R . . H12B H 0.5722 0.7783 0.2440 0.095 Uiso 1 1 calc R . . C13 C 0.6387(6) 0.9704(5) 0.1905(5) 0.1047(15) Uani 1 1 d . . . H13A H 0.5611 1.0097 0.2572 0.157 Uiso 1 1 calc R . . H13B H 0.6453 1.0427 0.1115 0.157 Uiso 1 1 calc R . . H13C H 0.7491 0.9384 0.2204 0.157 Uiso 1 1 calc R . . C14 C 1.1716(4) 0.5491(3) -0.2863(3) 0.0542(7) Uani 1 1 d . . . C15 C 1.4764(5) 0.6376(4) -0.3853(4) 0.0887(12) Uani 1 1 d . . . H15A H 1.5393 0.5450 -0.3470 0.106 Uiso 1 1 calc R . . H15B H 1.4436 0.6303 -0.4681 0.106 Uiso 1 1 calc R . . C16 C 1.5858(6) 0.7452(5) -0.4099(5) 0.1179(17) Uani 1 1 d . . . H16A H 1.6838 0.7189 -0.4691 0.177 Uiso 1 1 calc R . . H16B H 1.6213 0.7506 -0.3285 0.177 Uiso 1 1 calc R . . H16C H 1.5242 0.8368 -0.4484 0.177 Uiso 1 1 calc R . . N1 N 0.7632(3) 0.4995(2) -0.1023(2) 0.0505(6) Uani 1 1 d . . . O1 O 0.5188(3) 0.6442(2) 0.0646(2) 0.0752(7) Uani 1 1 d . . . O2 O 0.6967(3) 0.7924(2) 0.0623(2) 0.0608(6) Uani 1 1 d . . . O3 O 1.2309(3) 0.4620(2) -0.3540(2) 0.0757(7) Uani 1 1 d . . . S1 S 1.28632(11) 0.68205(10) -0.27495(10) 0.0742(3) Uani 1 1 d . . . HN1 H 0.678(4) 0.458(4) -0.077(3) 0.074(11) Uiso 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 0.0503(16) 0.0449(15) 0.0548(18) -0.0172(12) -0.0020(13) -0.0092(12) C2 0.0596(18) 0.0465(16) 0.0620(19) -0.0173(13) 0.0014(14) -0.0097(13) C3 0.070(2) 0.0432(16) 0.087(3) -0.0212(16) 0.0062(18) -0.0108(14) C4 0.088(3) 0.057(2) 0.097(3) -0.042(2) -0.006(2) -0.0136(18) C5 0.116(3) 0.078(2) 0.067(2) -0.0386(19) -0.004(2) -0.023(2) C6 0.099(3) 0.0585(19) 0.059(2) -0.0172(15) -0.0053(18) -0.0246(18) C7 0.0518(16) 0.0421(14) 0.0477(16) -0.0136(12) -0.0029(12) -0.0088(12) C8 0.0529(16) 0.0408(14) 0.0508(17) -0.0109(12) -0.0035(13) -0.0114(12) C9 0.0559(17) 0.0388(14) 0.0564(18) -0.0136(12) -0.0050(13) -0.0132(12) C10 0.0515(16) 0.0401(14) 0.0542(17) -0.0153(12) -0.0016(13) -0.0107(12) C11 0.0554(17) 0.0448(15) 0.0635(19) -0.0172(13) -0.0007(14) -0.0124(13) C12 0.075(2) 0.075(2) 0.096(3) -0.051(2) 0.0261(19) -0.0209(18) C13 0.102(3) 0.112(3) 0.122(4) -0.080(3) 0.022(3) -0.031(3) C14 0.0599(18) 0.0482(16) 0.0560(18) -0.0136(13) -0.0017(14) -0.0129(13) C15 0.070(2) 0.098(3) 0.106(3) -0.044(2) 0.026(2) -0.031(2) C16 0.102(3) 0.121(4) 0.138(4) -0.057(3) 0.056(3) -0.054(3) N1 0.0533(14) 0.0446(13) 0.0575(15) -0.0172(11) 0.0013(12) -0.0151(11) O1 0.0605(14) 0.0733(15) 0.1034(19) -0.0455(13) 0.0197(12) -0.0287(11) O2 0.0602(12) 0.0553(12) 0.0748(14) -0.0347(10) 0.0122(10) -0.0184(10) O3 0.0736(15) 0.0733(15) 0.0877(17) -0.0438(13) 0.0199(12) -0.0205(12) S1 0.0673(6) 0.0764(6) 0.0900(7) -0.0400(5) 0.0184(5) -0.0321(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.382(4) . ? C1 C2 1.385(4) . ? C1 C7 1.476(4) . ? C2 C3 1.374(4) . ? C2 H2 0.9300 . ? C3 C4 1.370(5) . ? C3 H3 0.9300 . ? C4 C5 1.373(5) . ? C4 H4 0.9300 . ? C5 C6 1.376(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.348(4) . ? C7 C8 1.404(4) . ? C8 C9 1.406(4) . ? C8 C14 1.462(4) . ? C9 C10 1.365(4) . ? C9 H9 0.9300 . ? C10 N1 1.371(3) . ? C10 C11 1.453(4) . ? C11 O1 1.209(3) . ? C11 O2 1.328(3) . ? C12 C13 1.437(5) . ? C12 O2 1.461(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O3 1.211(3) . ? C14 S1 1.777(3) . ? C15 C16 1.462(5) . ? C15 S1 1.820(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? N1 HN1 0.85(3) . ? 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 118.1(3) . . ? C6 C1 C7 122.4(3) . . ? C2 C1 C7 119.4(3) . . ? C3 C2 C1 121.2(3) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 120.4(3) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? N1 C7 C8 106.9(2) . . ? N1 C7 C1 119.2(2) . . ? C8 C7 C1 133.8(3) . . ? C7 C8 C9 106.8(2) . . ? C7 C8 C14 126.3(2) . . ? C9 C8 C14 126.7(2) . . ? C10 C9 C8 108.1(2) . . ? C10 C9 H9 125.9 . . ? C8 C9 H9 125.9 . . ? C9 C10 N1 107.3(2) . . ? C9 C10 C11 133.0(2) . . ? N1 C10 C11 119.6(2) . . ? O1 C11 O2 123.4(3) . . ? O1 C11 C10 123.9(3) . . ? O2 C11 C10 112.7(2) . . ? C13 C12 O2 109.5(3) . . ? C13 C12 H12A 109.8 . . ? O2 C12 H12A 109.8 . . ? C13 C12 H12B 109.8 . . ? O2 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O3 C14 C8 125.2(3) . . ? O3 C14 S1 120.8(2) . . ? C8 C14 S1 114.0(2) . . ? C16 C15 S1 111.8(3) . . ? C16 C15 H15A 109.3 . . ? S1 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? S1 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C7 N1 C10 110.7(2) . . ? C7 N1 HN1 124(2) . . ? C10 N1 HN1 125(2) . . ? C11 O2 C12 115.4(2) . . ? C14 S1 C15 99.98(16) . . ? 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) . . . . ? C7 C1 C2 C3 178.4(3) . . . . ? C1 C2 C3 C4 -0.4(5) . . . . ? C2 C3 C4 C5 0.0(5) . . . . ? C3 C4 C5 C6 0.6(6) . . . . ? C4 C5 C6 C1 -0.8(6) . . . . ? C2 C1 C6 C5 0.4(5) . . . . ? C7 C1 C6 C5 -177.8(3) . . . . ? C6 C1 C7 N1 130.7(3) . . . . ? C2 C1 C7 N1 -47.5(4) . . . . ? C6 C1 C7 C8 -53.6(5) . . . . ? C2 C1 C7 C8 128.2(3) . . . . ? N1 C7 C8 C9 0.4(3) . . . . ? C1 C7 C8 C9 -175.7(3) . . . . ? N1 C7 C8 C14 176.1(3) . . . . ? C1 C7 C8 C14 0.0(5) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? C14 C8 C9 C10 -176.3(3) . . . . ? C8 C9 C10 N1 0.5(3) . . . . ? C8 C9 C10 C11 179.1(3) . . . . ? C9 C10 C11 O1 174.1(3) . . . . ? N1 C10 C11 O1 -7.5(5) . . . . ? C9 C10 C11 O2 -6.5(5) . . . . ? N1 C10 C11 O2 171.9(2) . . . . ? C7 C8 C14 O3 7.1(5) . . . . ? C9 C8 C14 O3 -178.1(3) . . . . ? C7 C8 C14 S1 -172.7(2) . . . . ? C9 C8 C14 S1 2.2(4) . . . . ? C8 C7 N1 C10 -0.1(3) . . . . ? C1 C7 N1 C10 176.7(2) . . . . ? C9 C10 N1 C7 -0.3(3) . . . . ? C11 C10 N1 C7 -179.1(3) . . . . ? O1 C11 O2 C12 4.9(5) . . . . ? C10 C11 O2 C12 -174.5(3) . . . . ? C13 C12 O2 C11 -177.2(3) . . . . ? O3 C14 S1 C15 1.0(3) . . . . ? C8 C14 S1 C15 -179.2(2) . . . . ? C16 C15 S1 C14 171.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.331 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 949220' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_161b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 O4 S2' _chemical_formula_sum 'C19 H16 O4 S2' _chemical_formula_weight 372.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' 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 'P 21/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 13.510(4) _cell_length_b 8.068(3) _cell_length_c 17.081(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.751(6) _cell_angle_gamma 90.00 _cell_volume 1773.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3032 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 25.0 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details ? _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7945 _diffrn_reflns_av_R_equivalents 0.1046 _diffrn_reflns_av_sigmaI/netI 0.2288 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3032 _reflns_number_gt 1703 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3032 _refine_ls_number_parameters 226 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1312 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.2335 _refine_ls_wR_factor_gt 0.1795 _refine_ls_goodness_of_fit_ref 0.863 _refine_ls_restrained_S_all 0.863 _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 0.44721(9) 0.72001(14) 0.32173(8) 0.0444(4) Uani 1 1 d . . . O4 O 0.2780(2) 0.6944(4) 0.0913(2) 0.0507(9) Uani 1 1 d . . . C6 C 0.2069(4) 1.1757(6) 0.1921(4) 0.0546(14) Uani 1 1 d . . . H6A H 0.2467 1.1301 0.1617 0.066 Uiso 1 1 calc R . . C7 C 0.2050(3) 0.9000(6) 0.2594(3) 0.0478(13) Uani 1 1 d . . . C2 C 0.1142(4) 1.1464(7) 0.2897(4) 0.0563(14) Uani 1 1 d . . . H2A H 0.0898 1.0808 0.3246 0.068 Uiso 1 1 calc R . . C11 C 0.3525(3) 0.7316(5) 0.2252(3) 0.0391(11) Uani 1 1 d . . . O1 O 0.4468(3) 0.8744(4) 0.3634(2) 0.0616(10) Uani 1 1 d . . . O3 O 0.1946(3) 0.8241(5) 0.3167(3) 0.0746(12) Uani 1 1 d . . . C4 C 0.1265(4) 1.4106(7) 0.2305(5) 0.0711(18) Uani 1 1 d . . . H4A H 0.1123 1.5236 0.2266 0.085 Uiso 1 1 calc R . . C5 C 0.1817(4) 1.3428(7) 0.1844(4) 0.0662(17) Uani 1 1 d . . . H5A H 0.2027 1.4083 0.1476 0.079 Uiso 1 1 calc R . . O2 O 0.5406(2) 0.6677(5) 0.3064(2) 0.0629(11) Uani 1 1 d . . . C8 C 0.2532(3) 0.8156(5) 0.2031(3) 0.0392(11) Uani 1 1 d . . . C3 C 0.0913(4) 1.3147(7) 0.2827(4) 0.0699(18) Uani 1 1 d . . . H3A H 0.0523 1.3620 0.3133 0.084 Uiso 1 1 calc R . . C1 C 0.1729(3) 1.0765(6) 0.2452(3) 0.0425(12) Uani 1 1 d . . . C9 C 0.2128(4) 0.7877(6) 0.1207(3) 0.0488(13) Uani 1 1 d . . . C17 C 0.4120(3) 0.3997(6) 0.3492(3) 0.0458(12) Uani 1 1 d . . . H17A H 0.4369 0.3770 0.3051 0.055 Uiso 1 1 calc R . . C15 C 0.3425(4) 0.3035(6) 0.4547(3) 0.0506(14) Uani 1 1 d . . . C18 C 0.3050(5) 0.1654(8) 0.4976(4) 0.082(2) Uani 1 1 d . . . H18A H 0.3126 0.0615 0.4727 0.123 Uiso 1 1 calc R . . H18B H 0.2331 0.1829 0.4929 0.123 Uiso 1 1 calc R . . H18C H 0.3453 0.1637 0.5546 0.123 Uiso 1 1 calc R . . C14 C 0.3393(4) 0.4658(7) 0.4797(3) 0.0556(14) Uani 1 1 d . . . H14A H 0.3157 0.4883 0.5243 0.067 Uiso 1 1 calc R . . C12 C 0.4062(3) 0.5602(6) 0.3744(3) 0.0410(12) Uani 1 1 d . . . C16 C 0.3804(4) 0.2723(6) 0.3902(4) 0.0536(15) Uani 1 1 d . . . H16A H 0.3849 0.1634 0.3738 0.064 Uiso 1 1 calc R . . C13 C 0.3702(4) 0.5945(6) 0.4399(3) 0.0498(13) Uani 1 1 d . . . H13A H 0.3669 0.7033 0.4570 0.060 Uiso 1 1 calc R . . S2 S 0.09387(13) 0.8471(3) 0.05360(11) 0.1072(9) Uani 1 1 d . . . C10 C 0.3631(3) 0.6625(6) 0.1574(3) 0.0446(12) Uani 1 1 d . . . H10A H 0.4204 0.6010 0.1552 0.053 Uiso 1 1 calc R . . C19 C 0.0865(6) 0.7599(16) -0.0354(6) 0.191(6) Uani 1 1 d U . . H19A H 0.0214 0.7884 -0.0751 0.191 Uiso 1 1 calc R . . H19B H 0.0912 0.6417 -0.0289 0.191 Uiso 1 1 calc R . . H19C H 0.1426 0.7990 -0.0541 0.191 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 0.0425(7) 0.0410(7) 0.0472(8) 0.0027(6) 0.0100(5) -0.0043(5) O4 0.0555(19) 0.049(2) 0.045(2) -0.0010(16) 0.0126(16) 0.0113(15) C6 0.042(3) 0.045(3) 0.078(4) -0.001(3) 0.019(3) 0.003(2) C7 0.047(3) 0.047(3) 0.048(3) 0.007(3) 0.011(2) 0.003(2) C2 0.047(3) 0.051(3) 0.070(4) -0.007(3) 0.016(3) 0.003(2) C11 0.044(2) 0.030(2) 0.044(3) 0.006(2) 0.014(2) 0.0016(18) O1 0.082(2) 0.039(2) 0.055(2) -0.0044(17) 0.0079(18) -0.0127(16) O3 0.105(3) 0.064(3) 0.071(3) 0.023(2) 0.051(2) 0.024(2) C4 0.063(3) 0.043(3) 0.107(6) -0.007(3) 0.025(3) 0.005(3) C5 0.060(3) 0.046(3) 0.092(5) 0.008(3) 0.021(3) 0.006(2) O2 0.0372(17) 0.085(3) 0.068(3) 0.016(2) 0.0173(16) 0.0000(15) C8 0.040(2) 0.031(2) 0.048(3) 0.004(2) 0.015(2) 0.0033(17) C3 0.053(3) 0.059(4) 0.097(5) -0.013(4) 0.021(3) 0.015(3) C1 0.032(2) 0.042(3) 0.051(3) -0.006(2) 0.007(2) 0.0004(18) C9 0.051(3) 0.053(3) 0.041(3) 0.003(2) 0.011(2) 0.014(2) C17 0.049(3) 0.045(3) 0.042(3) -0.005(2) 0.012(2) 0.010(2) C15 0.051(3) 0.056(3) 0.038(3) 0.009(3) 0.003(2) -0.003(2) C18 0.096(4) 0.071(4) 0.066(4) 0.016(3) 0.007(3) -0.031(3) C14 0.073(3) 0.063(4) 0.041(3) 0.001(3) 0.034(3) 0.003(3) C12 0.037(2) 0.040(3) 0.042(3) -0.001(2) 0.006(2) 0.0016(18) C16 0.060(3) 0.034(3) 0.058(4) -0.002(3) 0.004(3) 0.003(2) C13 0.060(3) 0.042(3) 0.049(3) -0.008(3) 0.020(2) 0.009(2) S2 0.0800(12) 0.173(2) 0.0520(11) -0.0103(12) -0.0042(9) 0.0643(12) C10 0.039(2) 0.050(3) 0.043(3) 0.006(2) 0.010(2) 0.0070(19) C19 0.087(6) 0.329(16) 0.110(8) -0.103(9) -0.038(5) 0.072(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.429(4) . ? S1 O1 1.436(4) . ? S1 C11 1.754(5) . ? S1 C12 1.756(5) . ? O4 C9 1.366(6) . ? O4 C10 1.367(5) . ? C6 C5 1.387(7) . ? C6 C1 1.388(7) . ? C6 H6A 0.9300 . ? C7 O3 1.198(6) . ? C7 C8 1.481(7) . ? C7 C1 1.487(6) . ? C2 C1 1.376(7) . ? C2 C3 1.389(7) . ? C2 H2A 0.9300 . ? C11 C10 1.332(7) . ? C11 C8 1.447(6) . ? C4 C5 1.352(8) . ? C4 C3 1.371(9) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C8 C9 1.364(7) . ? C3 H3A 0.9300 . ? C9 S2 1.733(5) . ? C17 C12 1.375(6) . ? C17 C16 1.384(7) . ? C17 H17A 0.9300 . ? C15 C16 1.371(8) . ? C15 C14 1.382(7) . ? C15 C18 1.504(8) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C14 C13 1.374(7) . ? C14 H14A 0.9300 . ? C12 C13 1.377(7) . ? C16 H16A 0.9300 . ? C13 H13A 0.9300 . ? S2 C19 1.651(9) . ? C10 H10A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 119.0(2) . . ? O2 S1 C11 105.9(2) . . ? O1 S1 C11 107.9(2) . . ? O2 S1 C12 108.1(2) . . ? O1 S1 C12 109.5(2) . . ? C11 S1 C12 105.5(2) . . ? C9 O4 C10 105.9(4) . . ? C5 C6 C1 120.1(5) . . ? C5 C6 H6A 120.0 . . ? C1 C6 H6A 120.0 . . ? O3 C7 C8 118.7(5) . . ? O3 C7 C1 121.5(5) . . ? C8 C7 C1 119.9(5) . . ? C1 C2 C3 120.3(6) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C10 C11 C8 107.8(4) . . ? C10 C11 S1 123.7(3) . . ? C8 C11 S1 128.5(4) . . ? C5 C4 C3 120.8(6) . . ? C5 C4 H4A 119.6 . . ? C3 C4 H4A 119.6 . . ? C4 C5 C6 120.1(6) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C9 C8 C11 103.9(4) . . ? C9 C8 C7 128.9(4) . . ? C11 C8 C7 127.1(4) . . ? C4 C3 C2 119.6(6) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C2 C1 C6 119.1(5) . . ? C2 C1 C7 119.4(5) . . ? C6 C1 C7 121.4(5) . . ? C8 C9 O4 111.7(4) . . ? C8 C9 S2 129.5(4) . . ? O4 C9 S2 118.8(4) . . ? C12 C17 C16 119.0(5) . . ? C12 C17 H17A 120.5 . . ? C16 C17 H17A 120.5 . . ? C16 C15 C14 118.4(5) . . ? C16 C15 C18 121.3(5) . . ? C14 C15 C18 120.3(6) . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C13 C14 C15 121.4(5) . . ? C13 C14 H14A 119.3 . . ? C15 C14 H14A 119.3 . . ? C17 C12 C13 120.8(5) . . ? C17 C12 S1 118.3(4) . . ? C13 C12 S1 120.9(4) . . ? C15 C16 C17 121.3(5) . . ? C15 C16 H16A 119.3 . . ? C17 C16 H16A 119.3 . . ? C14 C13 C12 119.1(5) . . ? C14 C13 H13A 120.5 . . ? C12 C13 H13A 120.5 . . ? C19 S2 C9 106.0(3) . . ? C11 C10 O4 110.7(4) . . ? C11 C10 H10A 124.6 . . ? O4 C10 H10A 124.6 . . ? S2 C19 H19A 109.5 . . ? S2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? S2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 C11 C10 15.6(5) . . . . ? O1 S1 C11 C10 144.1(4) . . . . ? C12 S1 C11 C10 -98.9(4) . . . . ? O2 S1 C11 C8 -163.2(4) . . . . ? O1 S1 C11 C8 -34.7(5) . . . . ? C12 S1 C11 C8 82.3(4) . . . . ? C3 C4 C5 C6 -2.6(9) . . . . ? C1 C6 C5 C4 2.0(8) . . . . ? C10 C11 C8 C9 -0.2(5) . . . . ? S1 C11 C8 C9 178.7(4) . . . . ? C10 C11 C8 C7 175.5(5) . . . . ? S1 C11 C8 C7 -5.6(7) . . . . ? O3 C7 C8 C9 120.6(6) . . . . ? C1 C7 C8 C9 -60.8(7) . . . . ? O3 C7 C8 C11 -54.0(7) . . . . ? C1 C7 C8 C11 124.5(5) . . . . ? C5 C4 C3 C2 1.3(9) . . . . ? C1 C2 C3 C4 0.7(8) . . . . ? C3 C2 C1 C6 -1.3(7) . . . . ? C3 C2 C1 C7 174.2(4) . . . . ? C5 C6 C1 C2 -0.1(7) . . . . ? C5 C6 C1 C7 -175.5(4) . . . . ? O3 C7 C1 C2 -11.3(7) . . . . ? C8 C7 C1 C2 170.2(4) . . . . ? O3 C7 C1 C6 164.1(5) . . . . ? C8 C7 C1 C6 -14.5(7) . . . . ? C11 C8 C9 O4 0.3(5) . . . . ? C7 C8 C9 O4 -175.3(4) . . . . ? C11 C8 C9 S2 178.0(4) . . . . ? C7 C8 C9 S2 2.4(8) . . . . ? C10 O4 C9 C8 -0.3(5) . . . . ? C10 O4 C9 S2 -178.3(4) . . . . ? C16 C15 C14 C13 1.9(7) . . . . ? C18 C15 C14 C13 -178.0(5) . . . . ? C16 C17 C12 C13 0.5(6) . . . . ? C16 C17 C12 S1 179.8(3) . . . . ? O2 S1 C12 C17 -42.0(4) . . . . ? O1 S1 C12 C17 -173.1(3) . . . . ? C11 S1 C12 C17 71.0(4) . . . . ? O2 S1 C12 C13 137.3(4) . . . . ? O1 S1 C12 C13 6.2(4) . . . . ? C11 S1 C12 C13 -109.7(4) . . . . ? C14 C15 C16 C17 -1.9(7) . . . . ? C18 C15 C16 C17 178.1(4) . . . . ? C12 C17 C16 C15 0.7(7) . . . . ? C15 C14 C13 C12 -0.8(7) . . . . ? C17 C12 C13 C14 -0.4(7) . . . . ? S1 C12 C13 C14 -179.7(3) . . . . ? C8 C9 S2 C19 -174.4(7) . . . . ? O4 C9 S2 C19 3.2(7) . . . . ? C8 C11 C10 O4 0.1(5) . . . . ? S1 C11 C10 O4 -178.9(3) . . . . ? C9 O4 C10 C11 0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.421 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 965705'