# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Sekar Govindasamy' _publ_contact_author_email GSEKAR@IITM.AC.IN _publ_section_title ; An Efficient Copper Catalyzed Synthesis of Hexahydro-1H-phenothiazines ; loop_ _publ_author_name 'Sekar Govindasamy' 'D. J. C. Prasada' # Attachment 'compound No.10.cif' data_new _database_code_depnum_ccdc_archive 'CCDC 737914' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 N O2 S2' _chemical_formula_sum 'C18 H19 N O2 S2' _chemical_formula_weight 345.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _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 13.5039(4) _cell_length_b 12.3329(3) _cell_length_c 10.3136(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.7070(10) _cell_angle_gamma 90.00 _cell_volume 1709.14(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4974 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 28.03 _exptl_crystal_description Rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8773 _exptl_absorpt_correction_T_max 0.9329 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker Apex II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11807 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4106 _reflns_number_gt 3009 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II,Bruker,2004' _computing_cell_refinement 'APEXII/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _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^)+(0.1000P)^2^+0.2650P] 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 4106 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1485 _refine_ls_wR_factor_gt 0.1224 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 0.42780(16) 0.16099(16) 0.3297(2) 0.0465(5) Uani 1 1 d . . . H1 H 0.4712 0.1342 0.4047 0.056 Uiso 1 1 calc R . . C2 C 0.48893(19) 0.23196(18) 0.2470(3) 0.0567(6) Uani 1 1 d . . . H2A H 0.5378 0.2736 0.3014 0.068 Uiso 1 1 calc R . . H2B H 0.4465 0.2815 0.1937 0.068 Uiso 1 1 calc R . . C3 C 0.54015(18) 0.1510(2) 0.1613(3) 0.0577(6) Uani 1 1 d . . . H3A H 0.5251 0.1685 0.0698 0.069 Uiso 1 1 calc R . . H3B H 0.6118 0.1528 0.1823 0.069 Uiso 1 1 calc R . . C4 C 0.49863(17) 0.03827(19) 0.1913(3) 0.0532(6) Uani 1 1 d . . . H4A H 0.4893 -0.0064 0.1136 0.064 Uiso 1 1 calc R . . H4B H 0.5418 0.0008 0.2575 0.064 Uiso 1 1 calc R . . C5 C 0.39980(15) 0.06783(16) 0.2404(2) 0.0417(5) Uani 1 1 d . . . H5 H 0.3565 0.0962 0.1662 0.050 Uiso 1 1 calc R . . C6 C 0.30742(14) -0.00004(15) 0.42604(18) 0.0358(4) Uani 1 1 d . . . C7 C 0.29029(17) -0.08882(17) 0.5042(2) 0.0473(5) Uani 1 1 d . . . H7 H 0.3105 -0.1575 0.4807 0.057 Uiso 1 1 calc R . . C8 C 0.24348(19) -0.0757(2) 0.6165(2) 0.0588(6) Uani 1 1 d . . . H8 H 0.2297 -0.1358 0.6662 0.071 Uiso 1 1 calc R . . C9 C 0.2172(2) 0.0267(2) 0.6545(2) 0.0629(7) Uani 1 1 d . . . H9 H 0.1836 0.0355 0.7283 0.075 Uiso 1 1 calc R . . C10 C 0.24053(18) 0.11553(19) 0.5841(2) 0.0526(5) Uani 1 1 d . . . H10 H 0.2260 0.1845 0.6133 0.063 Uiso 1 1 calc R . . C11 C 0.28545(15) 0.10407(15) 0.46970(19) 0.0391(4) Uani 1 1 d . . . C12 C 0.16968(14) 0.00799(16) 0.1462(2) 0.0387(4) Uani 1 1 d . . . C13 C 0.16856(16) 0.06130(18) 0.0291(2) 0.0475(5) Uani 1 1 d . . . H13 H 0.2171 0.0468 -0.0264 0.057 Uiso 1 1 calc R . . C14 C 0.09479(18) 0.1367(2) -0.0060(2) 0.0563(6) Uani 1 1 d . . . H14 H 0.0939 0.1720 -0.0858 0.068 Uiso 1 1 calc R . . C15 C 0.02297(17) 0.16027(19) 0.0751(3) 0.0562(6) Uani 1 1 d . . . C16 C 0.02529(17) 0.1055(2) 0.1926(3) 0.0598(7) Uani 1 1 d . . . H16 H -0.0228 0.1207 0.2485 0.072 Uiso 1 1 calc R . . C17 C 0.09707(16) 0.0291(2) 0.2285(2) 0.0508(5) Uani 1 1 d . . . H17 H 0.0968 -0.0079 0.3070 0.061 Uiso 1 1 calc R . . C18 C -0.0552(2) 0.2445(3) 0.0361(4) 0.0904(10) Uani 1 1 d . . . H18A H -0.0275 0.3155 0.0517 0.136 Uiso 1 1 calc R . . H18B H -0.1106 0.2349 0.0865 0.136 Uiso 1 1 calc R . . H18C H -0.0773 0.2367 -0.0548 0.136 Uiso 1 1 calc R . . N1 N 0.34432(12) -0.01951(12) 0.30129(16) 0.0371(4) Uani 1 1 d . . . O1 O 0.31898(12) -0.10432(13) 0.08317(15) 0.0542(4) Uani 1 1 d . . . O2 O 0.22421(12) -0.17313(11) 0.25816(16) 0.0553(4) Uani 1 1 d . . . S1 S 0.26571(4) -0.08431(4) 0.19306(5) 0.04036(17) Uani 1 1 d . . . S2 S 0.31953(4) 0.22199(4) 0.38764(6) 0.04909(19) 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 0.0492(12) 0.0383(10) 0.0524(12) -0.0011(9) 0.0077(10) -0.0055(9) C2 0.0579(14) 0.0447(12) 0.0693(16) 0.0001(11) 0.0161(12) -0.0156(10) C3 0.0487(13) 0.0609(14) 0.0657(15) 0.0042(12) 0.0174(11) -0.0075(11) C4 0.0490(13) 0.0493(12) 0.0633(15) -0.0059(10) 0.0158(11) -0.0016(10) C5 0.0436(11) 0.0358(9) 0.0464(11) -0.0019(8) 0.0076(9) -0.0027(8) C6 0.0360(10) 0.0348(9) 0.0354(9) 0.0025(7) -0.0029(8) -0.0041(7) C7 0.0520(13) 0.0391(10) 0.0485(12) 0.0076(9) -0.0067(10) -0.0073(9) C8 0.0702(16) 0.0602(14) 0.0441(12) 0.0146(11) -0.0036(11) -0.0205(12) C9 0.0771(17) 0.0729(17) 0.0404(12) 0.0024(11) 0.0139(12) -0.0147(13) C10 0.0664(15) 0.0508(12) 0.0415(11) -0.0064(9) 0.0101(10) -0.0047(10) C11 0.0425(11) 0.0375(9) 0.0368(10) -0.0008(8) 0.0010(8) -0.0036(8) C12 0.0337(10) 0.0396(10) 0.0425(11) -0.0097(8) 0.0019(8) -0.0022(7) C13 0.0448(12) 0.0542(12) 0.0440(12) -0.0046(9) 0.0066(9) 0.0061(9) C14 0.0570(14) 0.0584(13) 0.0520(13) 0.0040(11) -0.0013(11) 0.0072(11) C15 0.0427(12) 0.0533(13) 0.0701(16) -0.0146(11) -0.0059(11) 0.0073(10) C16 0.0372(12) 0.0786(17) 0.0648(16) -0.0179(13) 0.0112(11) 0.0056(11) C17 0.0413(12) 0.0630(14) 0.0492(12) -0.0035(10) 0.0094(10) -0.0019(10) C18 0.0732(19) 0.084(2) 0.110(3) -0.0146(19) -0.0095(18) 0.0374(17) N1 0.0387(9) 0.0304(7) 0.0419(9) -0.0038(6) 0.0023(7) -0.0016(6) O1 0.0548(9) 0.0558(9) 0.0520(9) -0.0193(7) 0.0060(7) 0.0092(7) O2 0.0680(10) 0.0326(7) 0.0634(10) -0.0043(7) -0.0032(8) -0.0130(7) S1 0.0442(3) 0.0306(2) 0.0458(3) -0.00938(19) 0.0022(2) -0.00021(18) S2 0.0643(4) 0.0296(3) 0.0558(4) 0.0003(2) 0.0184(3) 0.0019(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 C1 C5 1.497(3) . ? C1 C2 1.522(3) . ? C1 S2 1.798(2) . ? C1 H1 0.9800 . ? C2 C3 1.542(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.542(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.518(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.486(2) . ? C5 H5 0.9800 . ? C6 C7 1.393(3) . ? C6 C11 1.402(3) . ? C6 N1 1.445(2) . ? C7 C8 1.383(3) . ? C7 H7 0.9300 . ? C8 C9 1.380(4) . ? C8 H8 0.9300 . ? C9 C10 1.368(3) . ? C9 H9 0.9300 . ? C10 C11 1.386(3) . ? C10 H10 0.9300 . ? C11 S2 1.766(2) . ? C12 C13 1.374(3) . ? C12 C17 1.384(3) . ? C12 S1 1.757(2) . ? C13 C14 1.384(3) . ? C13 H13 0.9300 . ? C14 C15 1.373(3) . ? C14 H14 0.9300 . ? C15 C16 1.385(4) . ? C15 C18 1.507(3) . ? C16 C17 1.376(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N1 S1 1.6661(16) . ? O1 S1 1.4230(15) . ? O2 S1 1.4282(15) . ? 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 C5 C1 C2 102.37(17) . . ? C5 C1 S2 111.19(15) . . ? C2 C1 S2 116.73(16) . . ? C5 C1 H1 108.7 . . ? C2 C1 H1 108.7 . . ? S2 C1 H1 108.7 . . ? C1 C2 C3 104.37(17) . . ? C1 C2 H2A 110.9 . . ? C3 C2 H2A 110.9 . . ? C1 C2 H2B 110.9 . . ? C3 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? C4 C3 C2 106.03(17) . . ? C4 C3 H3A 110.5 . . ? C2 C3 H3A 110.5 . . ? C4 C3 H3B 110.5 . . ? C2 C3 H3B 110.5 . . ? H3A C3 H3B 108.7 . . ? C5 C4 C3 101.51(18) . . ? C5 C4 H4A 111.5 . . ? C3 C4 H4A 111.5 . . ? C5 C4 H4B 111.5 . . ? C3 C4 H4B 111.5 . . ? H4A C4 H4B 109.3 . . ? N1 C5 C1 113.77(16) . . ? N1 C5 C4 117.63(17) . . ? C1 C5 C4 102.31(17) . . ? N1 C5 H5 107.5 . . ? C1 C5 H5 107.5 . . ? C4 C5 H5 107.5 . . ? C7 C6 C11 118.78(18) . . ? C7 C6 N1 118.46(17) . . ? C11 C6 N1 122.73(16) . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C9 C8 C7 119.8(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.9(2) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C6 119.40(18) . . ? C10 C11 S2 118.73(16) . . ? C6 C11 S2 121.78(15) . . ? C13 C12 C17 120.2(2) . . ? C13 C12 S1 119.67(15) . . ? C17 C12 S1 120.14(17) . . ? C12 C13 C14 119.7(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 121.1(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 118.3(2) . . ? C14 C15 C18 120.1(3) . . ? C16 C15 C18 121.6(2) . . ? C17 C16 C15 121.6(2) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C12 119.1(2) . . ? C16 C17 H17 120.4 . . ? C12 C17 H17 120.4 . . ? 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 . . ? C6 N1 C5 119.24(14) . . ? C6 N1 S1 115.03(12) . . ? C5 N1 S1 112.27(13) . . ? O1 S1 O2 119.64(9) . . ? O1 S1 N1 106.14(9) . . ? O2 S1 N1 107.85(9) . . ? O1 S1 C12 108.13(10) . . ? O2 S1 C12 108.23(10) . . ? N1 S1 C12 106.08(8) . . ? C11 S2 C1 94.23(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 C5 C1 C2 C3 -32.0(2) . . . . ? S2 C1 C2 C3 -153.66(17) . . . . ? C1 C2 C3 C4 4.7(3) . . . . ? C2 C3 C4 C5 23.9(2) . . . . ? C2 C1 C5 N1 175.94(17) . . . . ? S2 C1 C5 N1 -58.7(2) . . . . ? C2 C1 C5 C4 48.0(2) . . . . ? S2 C1 C5 C4 173.38(15) . . . . ? C3 C4 C5 N1 -169.71(19) . . . . ? C3 C4 C5 C1 -44.3(2) . . . . ? C11 C6 C7 C8 6.3(3) . . . . ? N1 C6 C7 C8 -171.85(19) . . . . ? C6 C7 C8 C9 -2.8(3) . . . . ? C7 C8 C9 C10 -2.3(4) . . . . ? C8 C9 C10 C11 3.8(4) . . . . ? C9 C10 C11 C6 -0.1(3) . . . . ? C9 C10 C11 S2 -176.77(19) . . . . ? C7 C6 C11 C10 -4.8(3) . . . . ? N1 C6 C11 C10 173.23(18) . . . . ? C7 C6 C11 S2 171.69(15) . . . . ? N1 C6 C11 S2 -10.3(3) . . . . ? C17 C12 C13 C14 0.4(3) . . . . ? S1 C12 C13 C14 -177.86(17) . . . . ? C12 C13 C14 C15 0.7(4) . . . . ? C13 C14 C15 C16 -0.8(4) . . . . ? C13 C14 C15 C18 178.6(2) . . . . ? C14 C15 C16 C17 -0.1(4) . . . . ? C18 C15 C16 C17 -179.6(2) . . . . ? C15 C16 C17 C12 1.2(4) . . . . ? C13 C12 C17 C16 -1.3(3) . . . . ? S1 C12 C17 C16 176.92(18) . . . . ? C7 C6 N1 C5 -156.07(18) . . . . ? C11 C6 N1 C5 25.9(3) . . . . ? C7 C6 N1 S1 66.1(2) . . . . ? C11 C6 N1 S1 -111.93(18) . . . . ? C1 C5 N1 C6 11.0(2) . . . . ? C4 C5 N1 C6 130.6(2) . . . . ? C1 C5 N1 S1 149.88(15) . . . . ? C4 C5 N1 S1 -90.6(2) . . . . ? C6 N1 S1 O1 -174.62(13) . . . . ? C5 N1 S1 O1 44.68(15) . . . . ? C6 N1 S1 O2 -45.27(15) . . . . ? C5 N1 S1 O2 174.04(13) . . . . ? C6 N1 S1 C12 70.51(14) . . . . ? C5 N1 S1 C12 -70.19(14) . . . . ? C13 C12 S1 O1 -11.5(2) . . . . ? C17 C12 S1 O1 170.21(16) . . . . ? C13 C12 S1 O2 -142.51(17) . . . . ? C17 C12 S1 O2 39.24(19) . . . . ? C13 C12 S1 N1 101.97(18) . . . . ? C17 C12 S1 N1 -76.28(18) . . . . ? C10 C11 S2 C1 146.45(18) . . . . ? C6 C11 S2 C1 -30.09(18) . . . . ? C5 C1 S2 C11 62.77(16) . . . . ? C2 C1 S2 C11 179.68(18) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.356 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.064 # Attachment 'compound No.9.cif' data_djn-i-233 _database_code_depnum_ccdc_archive 'CCDC 737915' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 N O2 S2 ' _chemical_formula_sum 'C19 H21 N O2 S2' _chemical_formula_weight 359.49 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 14.6365(4) _cell_length_b 12.8539(3) _cell_length_c 9.8406(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.7590(10) _cell_angle_gamma 90.00 _cell_volume 1834.42(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4386 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 25.41 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8942 _exptl_absorpt_correction_T_max 0.9562 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker Apex II CCD area detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14118 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4396 _reflns_number_gt 3219 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II,Bruker,2004' _computing_cell_refinement 'APEXII/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4396 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1456 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 0.12130(12) 0.08076(14) 0.26337(18) 0.0379(4) Uani 1 1 d . . . H1 H 0.1544 0.1035 0.3516 0.045 Uiso 1 1 calc R . . C2 C 0.02520(14) 0.04607(18) 0.2879(2) 0.0556(5) Uani 1 1 d . . . H2A H -0.0100 0.0249 0.2017 0.067 Uiso 1 1 calc R . . H2B H 0.0301 -0.0132 0.3494 0.067 Uiso 1 1 calc R . . C3 C -0.02430(15) 0.1349(2) 0.3502(3) 0.0650(6) Uani 1 1 d . . . H3A H -0.0871 0.1140 0.3574 0.078 Uiso 1 1 calc R . . H3B H 0.0063 0.1489 0.4420 0.078 Uiso 1 1 calc R . . C4 C -0.02592(15) 0.2338(2) 0.2655(3) 0.0618(6) Uani 1 1 d . . . H4A H -0.0658 0.2237 0.1795 0.074 Uiso 1 1 calc R . . H4B H -0.0513 0.2901 0.3145 0.074 Uiso 1 1 calc R . . C5 C 0.06955(14) 0.26390(17) 0.2360(2) 0.0494(5) Uani 1 1 d . . . H5A H 0.1078 0.2821 0.3210 0.059 Uiso 1 1 calc R . . H5B H 0.0654 0.3242 0.1762 0.059 Uiso 1 1 calc R . . C6 C 0.11312(12) 0.17360(15) 0.16777(18) 0.0382(4) Uani 1 1 d . . . H6 H 0.0723 0.1547 0.0841 0.046 Uiso 1 1 calc R . . C7 C 0.23771(12) 0.09183(14) 0.03052(18) 0.0399(4) Uani 1 1 d . . . C8 C 0.27492(15) 0.09311(19) -0.0923(2) 0.0548(5) Uani 1 1 d . . . H8 H 0.2958 0.1551 -0.1258 0.066 Uiso 1 1 calc R . . C9 C 0.28051(18) 0.0014(2) -0.1639(2) 0.0664(7) Uani 1 1 d . . . H9 H 0.3072 0.0016 -0.2444 0.080 Uiso 1 1 calc R . . C10 C 0.24724(17) -0.0899(2) -0.1179(2) 0.0658(7) Uani 1 1 d . . . H10 H 0.2502 -0.1506 -0.1685 0.079 Uiso 1 1 calc R . . C11 C 0.20945(15) -0.09211(17) 0.0028(2) 0.0537(5) Uani 1 1 d . . . H11 H 0.1861 -0.1540 0.0330 0.064 Uiso 1 1 calc R . . C12 C 0.20622(12) -0.00131(14) 0.07977(18) 0.0402(4) Uani 1 1 d . . . C13 C 0.34419(12) 0.01732(15) 0.36335(19) 0.0425(4) Uani 1 1 d . . . C14 C 0.35127(15) 0.08677(17) 0.4713(2) 0.0533(5) Uani 1 1 d . . . H14 H 0.3075 0.0869 0.5315 0.064 Uiso 1 1 calc R . . C15 C 0.42389(18) 0.1559(2) 0.4890(3) 0.0688(7) Uani 1 1 d . . . H15 H 0.4291 0.2020 0.5625 0.083 Uiso 1 1 calc R . . C16 C 0.48877(16) 0.1581(2) 0.4002(3) 0.0727(7) Uani 1 1 d . . . C17 C 0.48061(16) 0.0872(2) 0.2920(3) 0.0711(8) Uani 1 1 d . . . H17 H 0.5243 0.0874 0.2316 0.085 Uiso 1 1 calc R . . C18 C 0.40929(14) 0.01704(19) 0.2729(2) 0.0575(6) Uani 1 1 d . . . H18 H 0.4046 -0.0300 0.2005 0.069 Uiso 1 1 calc R . . C19 C 0.5674(2) 0.2356(3) 0.4204(4) 0.1233(15) Uani 1 1 d . . . H19A H 0.5453 0.3007 0.4509 0.185 Uiso 1 1 calc R . . H19B H 0.5912 0.2457 0.3351 0.185 Uiso 1 1 calc R . . H19C H 0.6154 0.2095 0.4879 0.185 Uiso 1 1 calc R . . N1 N 0.17481(10) -0.00697(11) 0.21232(16) 0.0397(4) Uani 1 1 d . . . O1 O 0.20331(11) -0.06759(13) 0.45337(16) 0.0646(5) Uani 1 1 d . . . O2 O 0.27621(12) -0.15976(11) 0.27582(18) 0.0663(4) Uani 1 1 d . . . S1 S 0.22466(3) 0.20826(4) 0.12083(5) 0.04451(16) Uani 1 1 d . . . S2 S 0.24767(3) -0.06516(4) 0.33310(5) 0.04700(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 0.0374(8) 0.0378(10) 0.0392(9) 0.0025(8) 0.0080(7) -0.0024(7) C2 0.0462(11) 0.0608(14) 0.0621(13) 0.0077(11) 0.0159(9) -0.0095(9) C3 0.0459(11) 0.0874(19) 0.0662(13) -0.0008(13) 0.0238(10) 0.0011(11) C4 0.0478(11) 0.0726(17) 0.0668(14) -0.0080(12) 0.0150(10) 0.0128(11) C5 0.0501(11) 0.0460(12) 0.0530(11) -0.0029(9) 0.0102(9) 0.0099(9) C6 0.0386(9) 0.0380(10) 0.0386(8) -0.0002(8) 0.0073(7) 0.0013(7) C7 0.0416(9) 0.0395(11) 0.0392(9) 0.0021(8) 0.0081(7) 0.0049(7) C8 0.0635(12) 0.0575(14) 0.0469(11) 0.0134(10) 0.0208(9) 0.0160(10) C9 0.0783(16) 0.0798(19) 0.0446(11) 0.0001(12) 0.0208(10) 0.0291(13) C10 0.0781(16) 0.0624(17) 0.0552(13) -0.0189(12) 0.0026(11) 0.0216(13) C11 0.0565(12) 0.0434(12) 0.0598(12) -0.0103(10) 0.0027(9) 0.0030(9) C12 0.0398(9) 0.0385(11) 0.0417(9) -0.0012(8) 0.0036(7) 0.0024(7) C13 0.0396(9) 0.0395(11) 0.0487(10) 0.0126(9) 0.0065(7) 0.0080(8) C14 0.0560(12) 0.0554(14) 0.0479(11) 0.0069(10) 0.0051(9) 0.0049(10) C15 0.0712(15) 0.0619(17) 0.0673(14) 0.0030(12) -0.0120(12) -0.0045(12) C16 0.0504(13) 0.0679(17) 0.0930(19) 0.0300(15) -0.0154(12) -0.0084(11) C17 0.0417(11) 0.085(2) 0.0887(18) 0.0271(16) 0.0166(11) 0.0046(11) C18 0.0488(11) 0.0561(14) 0.0700(14) 0.0073(11) 0.0165(10) 0.0112(10) C19 0.082(2) 0.120(3) 0.156(3) 0.052(3) -0.027(2) -0.046(2) N1 0.0422(8) 0.0332(9) 0.0448(8) 0.0059(7) 0.0095(6) -0.0034(6) O1 0.0642(9) 0.0721(11) 0.0606(9) 0.0309(8) 0.0198(7) -0.0011(8) O2 0.0824(11) 0.0320(9) 0.0837(11) 0.0096(8) 0.0080(9) 0.0094(7) S1 0.0506(3) 0.0330(3) 0.0530(3) 0.0016(2) 0.0184(2) -0.00407(19) S2 0.0520(3) 0.0358(3) 0.0542(3) 0.0150(2) 0.0109(2) 0.00085(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.498(2) . ? C1 C6 1.514(2) . ? C1 C2 1.525(2) . ? C1 H1 0.9800 . ? C2 C3 1.525(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.518(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.515(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.523(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 S1 1.8112(18) . ? C6 H6 0.9800 . ? C7 C8 1.391(2) . ? C7 C12 1.393(3) . ? C7 S1 1.7641(19) . ? C8 C9 1.381(3) . ? C8 H8 0.9300 . ? C9 C10 1.370(4) . ? C9 H9 0.9300 . ? C10 C11 1.377(3) . ? C10 H10 0.9300 . ? C11 C12 1.396(3) . ? C11 H11 0.9300 . ? C12 N1 1.442(2) . ? C13 C14 1.381(3) . ? C13 C18 1.389(3) . ? C13 S2 1.759(2) . ? C14 C15 1.378(3) . ? C14 H14 0.9300 . ? C15 C16 1.375(4) . ? C15 H15 0.9300 . ? C16 C17 1.395(4) . ? C16 C19 1.514(4) . ? C17 C18 1.373(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N1 S2 1.6634(16) . ? O1 S2 1.4251(15) . ? O2 S2 1.4264(16) . ? 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 N1 C1 C6 112.71(13) . . ? N1 C1 C2 111.59(15) . . ? C6 C1 C2 109.35(15) . . ? N1 C1 H1 107.7 . . ? C6 C1 H1 107.7 . . ? C2 C1 H1 107.7 . . ? C3 C2 C1 110.04(18) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C2 112.31(18) . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 111.85(18) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C4 C5 C6 109.99(18) . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C1 C6 C5 109.22(15) . . ? C1 C6 S1 110.73(12) . . ? C5 C6 S1 111.74(14) . . ? C1 C6 H6 108.4 . . ? C5 C6 H6 108.4 . . ? S1 C6 H6 108.4 . . ? C8 C7 C12 119.94(18) . . ? C8 C7 S1 120.62(16) . . ? C12 C7 S1 119.36(13) . . ? C9 C8 C7 119.3(2) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C10 C9 C8 120.9(2) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 119.8(2) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C7 C12 C11 119.53(18) . . ? C7 C12 N1 121.25(16) . . ? C11 C12 N1 119.13(17) . . ? C14 C13 C18 120.5(2) . . ? C14 C13 S2 119.67(14) . . ? C18 C13 S2 119.65(16) . . ? C15 C14 C13 119.4(2) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C16 C15 C14 121.3(2) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 118.5(2) . . ? C15 C16 C19 120.5(3) . . ? C17 C16 C19 121.0(3) . . ? C18 C17 C16 121.3(2) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C13 119.0(2) . . ? C17 C18 H18 120.5 . . ? C13 C18 H18 120.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C12 N1 C1 120.68(14) . . ? C12 N1 S2 114.65(12) . . ? C1 N1 S2 114.37(12) . . ? C7 S1 C6 94.73(9) . . ? O1 S2 O2 120.01(10) . . ? O1 S2 N1 106.46(9) . . ? O2 S2 N1 107.14(9) . . ? O1 S2 C13 108.55(10) . . ? O2 S2 C13 108.02(9) . . ? N1 S2 C13 105.82(8) . . ? 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 N1 C1 C2 C3 175.60(17) . . . . ? C6 C1 C2 C3 -59.0(2) . . . . ? C1 C2 C3 C4 53.6(3) . . . . ? C2 C3 C4 C5 -52.1(3) . . . . ? C3 C4 C5 C6 55.1(3) . . . . ? N1 C1 C6 C5 -172.37(15) . . . . ? C2 C1 C6 C5 62.9(2) . . . . ? N1 C1 C6 S1 -48.91(18) . . . . ? C2 C1 C6 S1 -173.64(14) . . . . ? C4 C5 C6 C1 -60.7(2) . . . . ? C4 C5 C6 S1 176.49(15) . . . . ? C12 C7 C8 C9 -0.2(3) . . . . ? S1 C7 C8 C9 -177.13(17) . . . . ? C7 C8 C9 C10 2.1(4) . . . . ? C8 C9 C10 C11 -1.5(4) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C8 C7 C12 C11 -2.2(3) . . . . ? S1 C7 C12 C11 174.73(15) . . . . ? C8 C7 C12 N1 174.49(17) . . . . ? S1 C7 C12 N1 -8.6(2) . . . . ? C10 C11 C12 C7 2.8(3) . . . . ? C10 C11 C12 N1 -173.96(18) . . . . ? C18 C13 C14 C15 -0.2(3) . . . . ? S2 C13 C14 C15 -175.71(17) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C14 C15 C16 C17 -1.1(4) . . . . ? C14 C15 C16 C19 179.2(2) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C19 C16 C17 C18 -179.7(3) . . . . ? C16 C17 C18 C13 0.1(4) . . . . ? C14 C13 C18 C17 -0.3(3) . . . . ? S2 C13 C18 C17 175.20(17) . . . . ? C7 C12 N1 C1 37.6(2) . . . . ? C11 C12 N1 C1 -145.72(18) . . . . ? C7 C12 N1 S2 -105.56(17) . . . . ? C11 C12 N1 S2 71.13(19) . . . . ? C6 C1 N1 C12 -4.9(2) . . . . ? C2 C1 N1 C12 118.64(17) . . . . ? C6 C1 N1 S2 138.39(13) . . . . ? C2 C1 N1 S2 -98.12(16) . . . . ? C8 C7 S1 C6 139.76(17) . . . . ? C12 C7 S1 C6 -37.14(16) . . . . ? C1 C6 S1 C7 65.29(14) . . . . ? C5 C6 S1 C7 -172.72(14) . . . . ? C12 N1 S2 O1 -177.35(13) . . . . ? C1 N1 S2 O1 37.13(14) . . . . ? C12 N1 S2 O2 -47.80(15) . . . . ? C1 N1 S2 O2 166.69(12) . . . . ? C12 N1 S2 C13 67.28(14) . . . . ? C1 N1 S2 C13 -78.24(13) . . . . ? C14 C13 S2 O1 -17.17(18) . . . . ? C18 C13 S2 O1 167.28(16) . . . . ? C14 C13 S2 O2 -148.76(16) . . . . ? C18 C13 S2 O2 35.68(18) . . . . ? C14 C13 S2 N1 96.76(16) . . . . ? C18 C13 S2 N1 -78.79(17) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.293 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.052 # Attachment 'compound No.11.cif' data_djn-ii-45 _database_code_depnum_ccdc_archive 'CCDC 737916' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H23 N O2 S2' _chemical_formula_sum 'C20 H23 N O2 S2' _chemical_formula_weight 373.51 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 7.6290(15) _cell_length_b 11.646(2) _cell_length_c 11.722(2) _cell_angle_alpha 115.05(3) _cell_angle_beta 92.13(3) _cell_angle_gamma 92.44(3) _cell_volume 940.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3777 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 26.08 _exptl_crystal_description Rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9350 _exptl_absorpt_correction_T_max 0.9569 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker Apex II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15094 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 29.88 _reflns_number_total 5309 _reflns_number_gt 3377 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II,Bruker,2004' _computing_cell_refinement 'APEXII/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _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^)+(0.1000P)^2^+0.0523P] 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 5309 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1750 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.0523(3) 0.2277(2) 0.4509(2) 0.0400(5) Uani 1 1 d . . . H1 H -0.0315 0.2902 0.4537 0.048 Uiso 1 1 calc R . . C2 C 0.0058(4) 0.1784(3) 0.5483(3) 0.0565(7) Uani 1 1 d . . . H2A H -0.1021 0.1247 0.5182 0.068 Uiso 1 1 calc R . . H2B H 0.0978 0.1254 0.5534 0.068 Uiso 1 1 calc R . . C3 C -0.0180(5) 0.2787(4) 0.6800(3) 0.0868(11) Uani 1 1 d . . . H3A H -0.1321 0.3118 0.6783 0.104 Uiso 1 1 calc R . . H3B H -0.0240 0.2358 0.7350 0.104 Uiso 1 1 calc R . . C4 C 0.1070(6) 0.3863(4) 0.7398(3) 0.0961(12) Uani 1 1 d . . . H4A H 0.2176 0.3533 0.7515 0.115 Uiso 1 1 calc R . . H4B H 0.0680 0.4362 0.8234 0.115 Uiso 1 1 calc R . . C5 C 0.1461(6) 0.4739(3) 0.6845(3) 0.0929(12) Uani 1 1 d . . . H5A H 0.2126 0.5470 0.7488 0.112 Uiso 1 1 calc R . . H5B H 0.0350 0.5034 0.6683 0.112 Uiso 1 1 calc R . . C6 C 0.2441(4) 0.4338(2) 0.5655(3) 0.0563(7) Uani 1 1 d . . . H6A H 0.3662 0.4644 0.5897 0.068 Uiso 1 1 calc R . . H6B H 0.1976 0.4772 0.5173 0.068 Uiso 1 1 calc R . . C7 C 0.2397(3) 0.2927(2) 0.4781(2) 0.0362(5) Uani 1 1 d . . . H7 H 0.3103 0.2521 0.5206 0.043 Uiso 1 1 calc R . . C8 C 0.2273(3) 0.2662(2) 0.2521(2) 0.0392(5) Uani 1 1 d . . . C9 C 0.2719(4) 0.3384(3) 0.1866(3) 0.0542(6) Uani 1 1 d . . . H9 H 0.3639 0.4006 0.2179 0.065 Uiso 1 1 calc R . . C10 C 0.1791(4) 0.3171(3) 0.0755(3) 0.0709(9) Uani 1 1 d . . . H10 H 0.2114 0.3630 0.0304 0.085 Uiso 1 1 calc R . . C11 C 0.0373(4) 0.2271(4) 0.0307(3) 0.0714(9) Uani 1 1 d . . . H11 H -0.0235 0.2120 -0.0451 0.086 Uiso 1 1 calc R . . C12 C -0.0124(4) 0.1611(3) 0.0980(3) 0.0630(8) Uani 1 1 d . . . H12 H -0.1104 0.1040 0.0696 0.076 Uiso 1 1 calc R . . C13 C 0.0823(3) 0.1785(2) 0.2089(2) 0.0448(5) Uani 1 1 d . . . C14 C 0.4942(3) 0.0564(2) 0.2713(2) 0.0353(5) Uani 1 1 d . . . C15 C 0.5069(4) -0.0111(2) 0.3433(3) 0.0523(6) Uani 1 1 d . . . H15 H 0.5384 0.0307 0.4292 0.063 Uiso 1 1 calc R . . C16 C 0.4727(4) -0.1406(3) 0.2870(3) 0.0565(7) Uani 1 1 d . . . H16 H 0.4776 -0.1856 0.3362 0.068 Uiso 1 1 calc R . . C17 C 0.4310(3) -0.2053(2) 0.1591(3) 0.0480(6) Uani 1 1 d . . . C18 C 0.4212(4) -0.1355(2) 0.0881(3) 0.0512(6) Uani 1 1 d . . . H18 H 0.3931 -0.1771 0.0018 0.061 Uiso 1 1 calc R . . C19 C 0.4523(3) -0.0061(2) 0.1437(2) 0.0472(6) Uani 1 1 d . . . H19 H 0.4451 0.0395 0.0951 0.057 Uiso 1 1 calc R . . C20 C 0.3939(4) -0.3485(3) 0.0965(3) 0.0708(9) Uani 1 1 d . . . H20A H 0.4285 -0.3817 0.0111 0.106 Uiso 1 1 calc R . . H20B H 0.2705 -0.3684 0.0967 0.106 Uiso 1 1 calc R . . H20C H 0.4591 -0.3860 0.1422 0.106 Uiso 1 1 calc R . . N1 N 0.3292(2) 0.27962(16) 0.36302(18) 0.0360(4) Uani 1 1 d . . . O1 O 0.6083(2) 0.26188(16) 0.46644(17) 0.0504(4) Uani 1 1 d . . . O2 O 0.6069(2) 0.25976(16) 0.25388(18) 0.0508(4) Uani 1 1 d . . . S1 S 0.02497(8) 0.09396(6) 0.29738(7) 0.0503(2) Uani 1 1 d . . . S2 S 0.52648(6) 0.22322(5) 0.34290(5) 0.03746(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 0.0333(11) 0.0361(11) 0.0490(14) 0.0164(10) 0.0056(9) 0.0018(8) C2 0.0516(15) 0.0567(16) 0.0676(19) 0.0330(15) 0.0098(13) -0.0052(12) C3 0.105(3) 0.090(3) 0.064(2) 0.033(2) 0.022(2) -0.019(2) C4 0.130(3) 0.086(3) 0.058(2) 0.018(2) 0.026(2) -0.009(2) C5 0.122(3) 0.0556(19) 0.077(2) 0.0026(17) 0.051(2) -0.0088(18) C6 0.0615(16) 0.0413(13) 0.0519(16) 0.0061(12) 0.0142(13) -0.0059(11) C7 0.0313(10) 0.0353(11) 0.0390(12) 0.0130(9) 0.0030(9) -0.0003(8) C8 0.0361(11) 0.0402(11) 0.0394(13) 0.0144(10) 0.0041(9) 0.0089(8) C9 0.0542(15) 0.0556(16) 0.0579(18) 0.0287(14) 0.0060(13) 0.0075(11) C10 0.073(2) 0.097(3) 0.062(2) 0.0498(19) 0.0112(16) 0.0238(18) C11 0.0653(19) 0.102(3) 0.0469(18) 0.0308(18) -0.0026(14) 0.0182(17) C12 0.0499(15) 0.0703(19) 0.0536(18) 0.0126(15) -0.0091(13) 0.0044(13) C13 0.0401(12) 0.0415(12) 0.0442(14) 0.0099(11) -0.0006(10) 0.0047(9) C14 0.0302(10) 0.0367(11) 0.0380(12) 0.0146(9) 0.0056(8) 0.0036(8) C15 0.0703(17) 0.0483(14) 0.0391(14) 0.0200(12) -0.0030(12) 0.0039(12) C16 0.0770(19) 0.0470(14) 0.0530(17) 0.0284(13) 0.0033(14) 0.0061(12) C17 0.0451(13) 0.0364(12) 0.0578(17) 0.0145(12) 0.0101(11) 0.0072(9) C18 0.0622(15) 0.0454(14) 0.0384(14) 0.0099(11) 0.0075(11) 0.0059(11) C19 0.0624(15) 0.0439(13) 0.0367(13) 0.0175(11) 0.0094(11) 0.0082(10) C20 0.083(2) 0.0381(14) 0.080(2) 0.0133(14) 0.0170(17) 0.0052(13) N1 0.0299(9) 0.0359(9) 0.0396(11) 0.0134(8) 0.0034(7) 0.0028(7) O1 0.0361(8) 0.0512(10) 0.0508(11) 0.0100(8) -0.0073(7) 0.0005(7) O2 0.0406(9) 0.0483(10) 0.0669(12) 0.0270(9) 0.0162(8) -0.0011(7) S1 0.0444(3) 0.0376(3) 0.0585(4) 0.0116(3) -0.0001(3) -0.0076(2) S2 0.0283(3) 0.0362(3) 0.0437(3) 0.0132(2) 0.0034(2) -0.00086(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.526(3) . ? C1 C7 1.545(3) . ? C1 S1 1.811(3) . ? C1 H1 0.9800 . ? C2 C3 1.514(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.440(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.449(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.510(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.523(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N1 1.488(3) . ? C7 H7 0.9800 . ? C8 C13 1.396(3) . ? C8 C9 1.398(3) . ? C8 N1 1.435(3) . ? C9 C10 1.379(4) . ? C9 H9 0.9300 . ? C10 C11 1.392(5) . ? C10 H10 0.9300 . ? C11 C12 1.367(4) . ? C11 H11 0.9300 . ? C12 C13 1.396(4) . ? C12 H12 0.9300 . ? C13 S1 1.760(3) . ? C14 C19 1.376(3) . ? C14 C15 1.378(3) . ? C14 S2 1.761(2) . ? C15 C16 1.375(4) . ? C15 H15 0.9300 . ? C16 C17 1.380(4) . ? C16 H16 0.9300 . ? C17 C18 1.389(4) . ? C17 C20 1.520(3) . ? C18 C19 1.370(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N1 S2 1.6528(18) . ? O1 S2 1.4306(18) . ? O2 S2 1.4308(18) . ? 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 C7 111.8(2) . . ? C2 C1 S1 107.13(16) . . ? C7 C1 S1 112.37(16) . . ? C2 C1 H1 108.5 . . ? C7 C1 H1 108.5 . . ? S1 C1 H1 108.5 . . ? C3 C2 C1 115.9(2) . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2B 108.3 . . ? C1 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 120.9(3) . . ? C4 C3 H3A 107.1 . . ? C2 C3 H3A 107.1 . . ? C4 C3 H3B 107.1 . . ? C2 C3 H3B 107.1 . . ? H3A C3 H3B 106.8 . . ? C3 C4 C5 122.0(4) . . ? C3 C4 H4A 106.8 . . ? C5 C4 H4A 106.8 . . ? C3 C4 H4B 106.8 . . ? C5 C4 H4B 106.8 . . ? H4A C4 H4B 106.7 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5A 107.0 . . ? C6 C5 H5A 107.0 . . ? C4 C5 H5B 107.0 . . ? C6 C5 H5B 107.0 . . ? H5A C5 H5B 106.8 . . ? C5 C6 C7 117.9(2) . . ? C5 C6 H6A 107.8 . . ? C7 C6 H6A 107.8 . . ? C5 C6 H6B 107.8 . . ? C7 C6 H6B 107.8 . . ? H6A C6 H6B 107.2 . . ? N1 C7 C6 107.34(18) . . ? N1 C7 C1 113.95(18) . . ? C6 C7 C1 112.80(19) . . ? N1 C7 H7 107.5 . . ? C6 C7 H7 107.5 . . ? C1 C7 H7 107.5 . . ? C13 C8 C9 119.8(2) . . ? C13 C8 N1 119.1(2) . . ? C9 C8 N1 121.2(2) . . ? C10 C9 C8 119.8(3) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.3(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.8(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C8 C13 C12 119.2(3) . . ? C8 C13 S1 118.46(19) . . ? C12 C13 S1 122.3(2) . . ? C19 C14 C15 120.1(2) . . ? C19 C14 S2 119.70(17) . . ? C15 C14 S2 120.17(18) . . ? C16 C15 C14 119.4(2) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 121.4(2) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C16 C17 C18 118.1(2) . . ? C16 C17 C20 121.5(3) . . ? C18 C17 C20 120.3(3) . . ? C19 C18 C17 120.9(2) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C14 120.0(2) . . ? C18 C19 H19 120.0 . . ? C14 C19 H19 120.0 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C8 N1 C7 120.00(16) . . ? C8 N1 S2 117.17(15) . . ? C7 N1 S2 118.28(14) . . ? C13 S1 C1 96.60(11) . . ? O1 S2 O2 120.23(11) . . ? O1 S2 N1 106.29(10) . . ? O2 S2 N1 107.10(10) . . ? O1 S2 C14 108.58(11) . . ? O2 S2 C14 107.18(11) . . ? N1 S2 C14 106.75(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 C7 C1 C2 C3 69.1(3) . . . . ? S1 C1 C2 C3 -167.4(2) . . . . ? C1 C2 C3 C4 -46.3(5) . . . . ? C2 C3 C4 C5 58.5(6) . . . . ? C3 C4 C5 C6 -69.2(6) . . . . ? C4 C5 C6 C7 23.1(5) . . . . ? C5 C6 C7 N1 174.3(3) . . . . ? C5 C6 C7 C1 48.0(4) . . . . ? C2 C1 C7 N1 148.4(2) . . . . ? S1 C1 C7 N1 27.9(2) . . . . ? C2 C1 C7 C6 -88.9(3) . . . . ? S1 C1 C7 C6 150.62(19) . . . . ? C13 C8 C9 C10 -4.0(4) . . . . ? N1 C8 C9 C10 175.4(2) . . . . ? C8 C9 C10 C11 2.3(4) . . . . ? C9 C10 C11 C12 1.2(5) . . . . ? C10 C11 C12 C13 -2.9(5) . . . . ? C9 C8 C13 C12 2.2(4) . . . . ? N1 C8 C13 C12 -177.2(2) . . . . ? C9 C8 C13 S1 -177.47(18) . . . . ? N1 C8 C13 S1 3.1(3) . . . . ? C11 C12 C13 C8 1.2(4) . . . . ? C11 C12 C13 S1 -179.1(2) . . . . ? C19 C14 C15 C16 -1.8(4) . . . . ? S2 C14 C15 C16 176.7(2) . . . . ? C14 C15 C16 C17 2.0(4) . . . . ? C15 C16 C17 C18 -1.2(4) . . . . ? C15 C16 C17 C20 179.7(3) . . . . ? C16 C17 C18 C19 0.1(4) . . . . ? C20 C17 C18 C19 179.2(3) . . . . ? C17 C18 C19 C14 0.1(4) . . . . ? C15 C14 C19 C18 0.7(4) . . . . ? S2 C14 C19 C18 -177.79(19) . . . . ? C13 C8 N1 C7 -47.7(3) . . . . ? C9 C8 N1 C7 132.8(2) . . . . ? C13 C8 N1 S2 107.9(2) . . . . ? C9 C8 N1 S2 -71.5(2) . . . . ? C6 C7 N1 C8 -97.3(2) . . . . ? C1 C7 N1 C8 28.3(3) . . . . ? C6 C7 N1 S2 107.28(19) . . . . ? C1 C7 N1 S2 -127.07(16) . . . . ? C8 C13 S1 C1 43.5(2) . . . . ? C12 C13 S1 C1 -136.2(2) . . . . ? C2 C1 S1 C13 179.08(16) . . . . ? C7 C1 S1 C13 -57.76(18) . . . . ? C8 N1 S2 O1 172.96(15) . . . . ? C7 N1 S2 O1 -30.92(17) . . . . ? C8 N1 S2 O2 43.27(18) . . . . ? C7 N1 S2 O2 -160.61(15) . . . . ? C8 N1 S2 C14 -71.27(18) . . . . ? C7 N1 S2 C14 84.84(17) . . . . ? C19 C14 S2 O1 -166.30(18) . . . . ? C15 C14 S2 O1 15.2(2) . . . . ? C19 C14 S2 O2 -35.0(2) . . . . ? C15 C14 S2 O2 146.49(19) . . . . ? C19 C14 S2 N1 79.5(2) . . . . ? C15 C14 S2 N1 -99.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.449 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.055 # Attachment 'compound No.-13.cif' data_djn-ii-48 _database_code_depnum_ccdc_archive 'CCDC 737917' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 N O2 S2' _chemical_formula_sum 'C21 H25 N O2 S2' _chemical_formula_weight 387.54 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/n' _symmetry_space_group_name_Hall '-P 2yn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2666(3) _cell_length_b 13.1054(4) _cell_length_c 18.5231(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.842(2) _cell_angle_gamma 90.00 _cell_volume 1996.32(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2905 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 23.15 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9079 _exptl_absorpt_correction_T_max 0.9406 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker Apex II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14669 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 28.35 _reflns_number_total 4765 _reflns_number_gt 2501 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II,Bruker,2004' _computing_cell_refinement 'APEXII/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _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^)+(0.0590P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4765 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1179 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1397 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.2680(3) 0.37468(18) 0.16429(14) 0.0554(7) Uani 1 1 d . . . C2 C 0.2601(4) 0.4378(3) 0.22469(16) 0.0770(9) Uani 1 1 d . . . H2 H 0.2028 0.4176 0.2630 0.092 Uiso 1 1 calc R . . C3 C 0.3393(5) 0.5309(3) 0.2262(2) 0.0912(12) Uani 1 1 d . . . H3 H 0.3382 0.5722 0.2670 0.109 Uiso 1 1 calc R . . C4 C 0.4185(5) 0.5638(2) 0.1699(2) 0.0875(11) Uani 1 1 d . . . H4 H 0.4668 0.6279 0.1717 0.105 Uiso 1 1 calc R . . C5 C 0.4273(3) 0.50283(18) 0.11056(17) 0.0621(8) Uani 1 1 d . . . H5 H 0.4819 0.5253 0.0720 0.074 Uiso 1 1 calc R . . C6 C 0.3543(3) 0.40679(18) 0.10795(14) 0.0479(6) Uani 1 1 d . . . C7 C 0.2110(3) 0.29696(18) 0.01063(13) 0.0454(6) Uani 1 1 d . . . H7 H 0.2403 0.2367 -0.0165 0.055 Uiso 1 1 calc R . . C8 C 0.1416(3) 0.3759(2) -0.04438(16) 0.0642(8) Uani 1 1 d . . . H8A H 0.2198 0.3865 -0.0793 0.077 Uiso 1 1 calc R . . H8B H 0.1309 0.4400 -0.0191 0.077 Uiso 1 1 calc R . . C9 C -0.0225(4) 0.3507(2) -0.08603(18) 0.0789(9) Uani 1 1 d . . . H9A H -0.0556 0.4082 -0.1170 0.095 Uiso 1 1 calc R . . H9B H -0.1020 0.3434 -0.0513 0.095 Uiso 1 1 calc R . . C10 C -0.0278(5) 0.2544(3) -0.1331(2) 0.1026(13) Uani 1 1 d . . . H10A H -0.1320 0.2531 -0.1624 0.123 Uiso 1 1 calc R . . H10B H 0.0555 0.2608 -0.1661 0.123 Uiso 1 1 calc R . . C11 C -0.0048(4) 0.1520(3) -0.0948(2) 0.0900(11) Uani 1 1 d . . . H11A H -0.0459 0.0991 -0.1284 0.108 Uiso 1 1 calc R . . H11B H 0.1108 0.1404 -0.0835 0.108 Uiso 1 1 calc R . . C12 C -0.0854(4) 0.1402(2) -0.0262(2) 0.0844(10) Uani 1 1 d . . . H12A H -0.1306 0.0719 -0.0257 0.101 Uiso 1 1 calc R . . H12B H -0.1759 0.1876 -0.0283 0.101 Uiso 1 1 calc R . . C13 C 0.0177(4) 0.1567(2) 0.04534(18) 0.0719(9) Uani 1 1 d . . . H13A H 0.1082 0.1094 0.0472 0.086 Uiso 1 1 calc R . . H13B H -0.0474 0.1377 0.0840 0.086 Uiso 1 1 calc R . . C14 C 0.0870(3) 0.26288(17) 0.06266(15) 0.0528(7) Uani 1 1 d . . . H14 H -0.0030 0.3119 0.0592 0.063 Uiso 1 1 calc R . . C15 C 0.5673(3) 0.18189(17) 0.09526(14) 0.0440(6) Uani 1 1 d . . . C16 C 0.6590(4) 0.1967(2) 0.16112(16) 0.0657(8) Uani 1 1 d . . . H16 H 0.6986 0.2613 0.1742 0.079 Uiso 1 1 calc R . . C17 C 0.6910(4) 0.1156(2) 0.20703(17) 0.0763(9) Uani 1 1 d . . . H17 H 0.7517 0.1262 0.2515 0.092 Uiso 1 1 calc R . . C18 C 0.6358(4) 0.0189(2) 0.18926(17) 0.0668(8) Uani 1 1 d . . . C19 C 0.5423(4) 0.00594(19) 0.12399(17) 0.0655(8) Uani 1 1 d . . . H19 H 0.5019 -0.0585 0.1113 0.079 Uiso 1 1 calc R . . C20 C 0.5071(3) 0.08699(18) 0.07680(14) 0.0548(7) Uani 1 1 d . . . H20 H 0.4433 0.0770 0.0331 0.066 Uiso 1 1 calc R . . C21 C 0.6792(5) -0.0711(2) 0.23881(19) 0.1030(13) Uani 1 1 d . . . H21A H 0.7948 -0.0812 0.2435 0.155 Uiso 1 1 calc R . . H21B H 0.6262 -0.1313 0.2186 0.155 Uiso 1 1 calc R . . H21C H 0.6440 -0.0579 0.2857 0.155 Uiso 1 1 calc R . . N1 N 0.3631(2) 0.34015(13) 0.04744(11) 0.0434(5) Uani 1 1 d . . . O1 O 0.6604(2) 0.35809(13) 0.05400(11) 0.0656(5) Uani 1 1 d . . . O2 O 0.5146(2) 0.24375(13) -0.03683(9) 0.0583(5) Uani 1 1 d . . . S1 S 0.53511(7) 0.28539(5) 0.03470(4) 0.0479(2) Uani 1 1 d . . . S2 S 0.17293(10) 0.25549(5) 0.15686(4) 0.0687(3) 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 0.0655(17) 0.0480(15) 0.0506(17) -0.0005(13) -0.0043(14) 0.0183(13) C2 0.086(2) 0.092(2) 0.0494(18) -0.0117(17) -0.0114(16) 0.032(2) C3 0.104(3) 0.081(3) 0.079(3) -0.039(2) -0.038(2) 0.035(2) C4 0.089(3) 0.0550(19) 0.108(3) -0.025(2) -0.039(2) 0.0137(17) C5 0.0573(17) 0.0383(15) 0.086(2) -0.0032(14) -0.0168(15) 0.0037(12) C6 0.0467(14) 0.0417(14) 0.0526(16) -0.0014(12) -0.0092(13) 0.0131(11) C7 0.0420(13) 0.0438(13) 0.0494(15) -0.0017(11) -0.0005(12) 0.0039(11) C8 0.0538(16) 0.0724(18) 0.0635(19) 0.0156(15) -0.0080(14) 0.0023(14) C9 0.0608(19) 0.093(2) 0.076(2) 0.0102(19) -0.0219(16) 0.0087(17) C10 0.090(3) 0.134(4) 0.077(2) -0.028(2) -0.023(2) 0.003(2) C11 0.076(2) 0.084(2) 0.105(3) -0.047(2) -0.019(2) 0.0123(19) C12 0.0519(18) 0.0600(19) 0.139(3) -0.028(2) 0.000(2) -0.0041(14) C13 0.0622(19) 0.0482(17) 0.107(3) -0.0053(17) 0.0183(19) -0.0030(14) C14 0.0470(14) 0.0427(15) 0.0696(18) -0.0016(13) 0.0098(13) 0.0025(11) C15 0.0405(13) 0.0394(14) 0.0515(16) -0.0044(11) 0.0011(12) 0.0106(10) C16 0.0700(19) 0.0515(17) 0.071(2) -0.0050(15) -0.0172(16) 0.0055(14) C17 0.080(2) 0.079(2) 0.064(2) 0.0037(18) -0.0220(17) 0.0122(18) C18 0.0596(18) 0.072(2) 0.068(2) 0.0197(17) 0.0035(16) 0.0223(16) C19 0.0723(19) 0.0419(16) 0.082(2) 0.0041(15) 0.0086(17) 0.0085(14) C20 0.0626(17) 0.0471(16) 0.0525(17) -0.0055(13) -0.0054(14) 0.0060(13) C21 0.099(3) 0.096(3) 0.113(3) 0.053(2) 0.005(2) 0.022(2) N1 0.0389(11) 0.0370(10) 0.0531(13) 0.0001(9) -0.0006(9) 0.0058(8) O1 0.0455(10) 0.0511(10) 0.0994(16) 0.0044(10) 0.0031(10) -0.0049(8) O2 0.0576(11) 0.0669(12) 0.0513(11) 0.0018(9) 0.0099(9) 0.0149(9) S1 0.0400(3) 0.0436(4) 0.0601(4) 0.0047(3) 0.0050(3) 0.0061(3) S2 0.0847(6) 0.0613(5) 0.0617(5) 0.0153(4) 0.0155(4) 0.0050(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.388(4) . ? C1 C2 1.398(4) . ? C1 S2 1.748(3) . ? C2 C3 1.384(5) . ? C2 H2 0.9300 . ? C3 C4 1.357(5) . ? C3 H3 0.9300 . ? C4 C5 1.367(4) . ? C4 H4 0.9300 . ? C5 C6 1.395(3) . ? C5 H5 0.9300 . ? C6 N1 1.429(3) . ? C7 N1 1.480(3) . ? C7 C8 1.523(3) . ? C7 C14 1.543(3) . ? C7 H7 0.9800 . ? C8 C9 1.527(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.531(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.520(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.503(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.515(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.527(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 S2 1.818(3) . ? C14 H14 0.9800 . ? C15 C20 1.370(3) . ? C15 C16 1.383(4) . ? C15 S1 1.763(2) . ? C16 C17 1.371(4) . ? C16 H16 0.9300 . ? C17 C18 1.375(4) . ? C17 H17 0.9300 . ? C18 C19 1.378(4) . ? C18 C21 1.516(4) . ? C19 C20 1.388(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? N1 S1 1.6315(19) . ? O1 S1 1.4259(18) . ? O2 S1 1.4270(18) . ? 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 119.5(3) . . ? C6 C1 S2 118.24(19) . . ? C2 C1 S2 122.3(2) . . ? C3 C2 C1 118.5(3) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C4 C3 C2 121.9(3) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 120.1(2) . . ? C1 C6 N1 118.4(2) . . ? C5 C6 N1 121.5(2) . . ? N1 C7 C8 107.03(19) . . ? N1 C7 C14 114.2(2) . . ? C8 C7 C14 112.7(2) . . ? N1 C7 H7 107.5 . . ? C8 C7 H7 107.5 . . ? C14 C7 H7 107.5 . . ? C7 C8 C9 116.5(2) . . ? C7 C8 H8A 108.2 . . ? C9 C8 H8A 108.2 . . ? C7 C8 H8B 108.2 . . ? C9 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? C8 C9 C10 116.0(3) . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C11 C10 C9 117.9(3) . . ? C11 C10 H10A 107.8 . . ? C9 C10 H10A 107.8 . . ? C11 C10 H10B 107.8 . . ? C9 C10 H10B 107.8 . . ? H10A C10 H10B 107.2 . . ? C12 C11 C10 116.1(3) . . ? C12 C11 H11A 108.3 . . ? C10 C11 H11A 108.3 . . ? C12 C11 H11B 108.3 . . ? C10 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? C11 C12 C13 117.8(3) . . ? C11 C12 H12A 107.8 . . ? C13 C12 H12A 107.8 . . ? C11 C12 H12B 107.8 . . ? C13 C12 H12B 107.8 . . ? H12A C12 H12B 107.2 . . ? C12 C13 C14 118.6(3) . . ? C12 C13 H13A 107.7 . . ? C14 C13 H13A 107.7 . . ? C12 C13 H13B 107.7 . . ? C14 C13 H13B 107.7 . . ? H13A C13 H13B 107.1 . . ? C13 C14 C7 113.1(2) . . ? C13 C14 S2 104.76(19) . . ? C7 C14 S2 113.29(18) . . ? C13 C14 H14 108.5 . . ? C7 C14 H14 108.5 . . ? S2 C14 H14 108.5 . . ? C20 C15 C16 120.0(2) . . ? C20 C15 S1 120.8(2) . . ? C16 C15 S1 119.14(19) . . ? C17 C16 C15 119.5(3) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 121.9(3) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C17 C18 C19 117.8(3) . . ? C17 C18 C21 121.4(3) . . ? C19 C18 C21 120.8(3) . . ? C18 C19 C20 121.4(3) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C15 C20 C19 119.3(3) . . ? C15 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C6 N1 C7 119.11(18) . . ? C6 N1 S1 119.81(16) . . ? C7 N1 S1 118.50(15) . . ? O1 S1 O2 120.18(12) . . ? O1 S1 N1 106.95(10) . . ? O2 S1 N1 106.25(11) . . ? O1 S1 C15 107.20(12) . . ? O2 S1 C15 107.01(11) . . ? N1 S1 C15 108.89(10) . . ? C1 S2 C14 99.02(12) . . ? 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 0.0(4) . . . . ? S2 C1 C2 C3 179.9(2) . . . . ? C1 C2 C3 C4 2.5(5) . . . . ? C2 C3 C4 C5 -2.6(5) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? C2 C1 C6 C5 -2.3(4) . . . . ? S2 C1 C6 C5 177.81(19) . . . . ? C2 C1 C6 N1 178.9(2) . . . . ? S2 C1 C6 N1 -1.0(3) . . . . ? C4 C5 C6 C1 2.2(4) . . . . ? C4 C5 C6 N1 -179.0(2) . . . . ? N1 C7 C8 C9 -176.3(2) . . . . ? C14 C7 C8 C9 -49.9(3) . . . . ? C7 C8 C9 C10 -61.2(4) . . . . ? C8 C9 C10 C11 66.9(5) . . . . ? C9 C10 C11 C12 39.5(5) . . . . ? C10 C11 C12 C13 -97.9(4) . . . . ? C11 C12 C13 C14 64.9(4) . . . . ? C12 C13 C14 C7 -64.9(3) . . . . ? C12 C13 C14 S2 171.2(2) . . . . ? N1 C7 C14 C13 -132.6(2) . . . . ? C8 C7 C14 C13 105.0(3) . . . . ? N1 C7 C14 S2 -13.6(2) . . . . ? C8 C7 C14 S2 -136.0(2) . . . . ? C20 C15 C16 C17 1.0(4) . . . . ? S1 C15 C16 C17 -177.0(2) . . . . ? C15 C16 C17 C18 0.7(5) . . . . ? C16 C17 C18 C19 -1.8(5) . . . . ? C16 C17 C18 C21 176.9(3) . . . . ? C17 C18 C19 C20 1.2(4) . . . . ? C21 C18 C19 C20 -177.4(3) . . . . ? C16 C15 C20 C19 -1.5(4) . . . . ? S1 C15 C20 C19 176.4(2) . . . . ? C18 C19 C20 C15 0.4(4) . . . . ? C1 C6 N1 C7 51.5(3) . . . . ? C5 C6 N1 C7 -127.3(2) . . . . ? C1 C6 N1 S1 -110.0(2) . . . . ? C5 C6 N1 S1 71.2(3) . . . . ? C8 C7 N1 C6 84.6(2) . . . . ? C14 C7 N1 C6 -40.9(3) . . . . ? C8 C7 N1 S1 -113.6(2) . . . . ? C14 C7 N1 S1 120.90(19) . . . . ? C6 N1 S1 O1 -37.7(2) . . . . ? C7 N1 S1 O1 160.64(17) . . . . ? C6 N1 S1 O2 -167.25(17) . . . . ? C7 N1 S1 O2 31.13(19) . . . . ? C6 N1 S1 C15 77.80(19) . . . . ? C7 N1 S1 C15 -83.82(19) . . . . ? C20 C15 S1 O1 -156.8(2) . . . . ? C16 C15 S1 O1 21.2(2) . . . . ? C20 C15 S1 O2 -26.6(2) . . . . ? C16 C15 S1 O2 151.3(2) . . . . ? C20 C15 S1 N1 87.9(2) . . . . ? C16 C15 S1 N1 -94.2(2) . . . . ? C6 C1 S2 C14 -43.5(2) . . . . ? C2 C1 S2 C14 136.6(2) . . . . ? C13 C14 S2 C1 172.80(18) . . . . ? C7 C14 S2 C1 49.13(19) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.513 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.044