####################################################################### # # 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_BVE389 _database_code_depnum_ccdc_archive 'CCDC 237705' _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2003-12-03 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 N O4 S' _chemical_formula_weight 393.44 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' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8047(2) _cell_length_b 11.9451(7) _cell_length_c 12.7864(9) _cell_angle_alpha 111.921(6) _cell_angle_beta 94.992(5) _cell_angle_gamma 92.605(4) _cell_volume 957.09(9) _cell_formula_units_Z 2 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used 23786 _cell_measurement_theta_min 3.020 _cell_measurement_theta_max 27.500 _exptl_crystal_description 'regular fragment' _exptl_crystal_colour 'colorless transparant' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(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 'Nonius KappaCCD on rotating anode' _diffrn_measurement_method 'area detector \f and \w scan' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 23786 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4377 _reflns_number_gt 3612 _reflns_number_observed 3612 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Nonius "EvalCCD" program suite' _computing_cell_refinement ? _computing_data_reduction 'Nonius "EvalCCD" program suite' _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), PATTY (Beurskens et al., 1987) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.3099P] 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 4377 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0373 _refine_ls_R_factor_obs 0.0373 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_all 0.0995 _refine_ls_wR_factor_gt 0.0935 _refine_ls_wR_factor_obs 0.0935 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_goodness_of_fit_all 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.26990(5) 0.19277(3) 0.24227(3) 0.03000(11) Uani 1 d . . . O1 O 0.09591(16) 0.25258(10) 0.27731(9) 0.0381(3) Uani 1 d . . . O2 O 0.40924(18) 0.24056(11) 0.18888(10) 0.0461(3) Uani 1 d . . . O3 O 0.03725(16) 0.32286(10) 0.54216(11) 0.0425(3) Uani 1 d . . . O4 O 0.33082(16) 0.40299(10) 0.52490(10) 0.0405(3) Uani 1 d . . . N1 N 0.38977(16) 0.18977(11) 0.35734(10) 0.0266(3) Uani 1 d . . . C1 C 0.6002(2) 0.16424(14) 0.35972(15) 0.0321(3) Uani 1 d . . . H1A H 0.656(3) 0.1931(15) 0.3077(15) 0.037(4) Uiso 1 d . . . H1B H 0.669(3) 0.2101(16) 0.4369(16) 0.039(5) Uiso 1 d . . . C2 C 0.6236(2) 0.03491(14) 0.32963(13) 0.0312(3) Uani 1 d . . . C3 C 0.6177(2) -0.07217(14) 0.30118(13) 0.0313(3) Uani 1 d . . . C4 C 0.5608(2) -0.19826(14) 0.27111(13) 0.0320(3) Uani 1 d . . . C5 C 0.6836(3) -0.28989(17) 0.22416(17) 0.0460(4) Uani 1 d . . . H5 H 0.819(3) -0.2711(18) 0.2111(17) 0.054(6) Uiso 1 d . . . C6 C 0.6144(3) -0.40927(18) 0.1971(2) 0.0582(5) Uani 1 d . . . H6 H 0.697(4) -0.474(2) 0.163(2) 0.079(7) Uiso 1 d . . . C7 C 0.4274(3) -0.43832(17) 0.21759(19) 0.0562(5) Uani 1 d . . . H7 H 0.379(3) -0.523(2) 0.2009(19) 0.067(6) Uiso 1 d . . . C8 C 0.3037(3) -0.34872(15) 0.26476(16) 0.0430(4) Uani 1 d . . . H8 H 0.176(3) -0.3662(17) 0.2838(16) 0.046(5) Uiso 1 d . . . C9 C 0.3675(2) -0.22798(13) 0.29123(12) 0.0306(3) Uani 1 d . . . C10 C 0.2500(2) -0.12909(13) 0.34071(12) 0.0294(3) Uani 1 d . . . C11 C 0.1872(2) -0.03239(13) 0.38091(12) 0.0284(3) Uani 1 d . . . C12 C 0.1181(2) 0.08824(13) 0.42726(13) 0.0285(3) Uani 1 d . . . H12A H 0.069(2) 0.1003(15) 0.4979(15) 0.034(4) Uiso 1 d . . . H12B H 0.011(2) 0.0957(14) 0.3764(14) 0.029(4) Uiso 1 d . . . C13 C 0.2824(2) 0.19035(13) 0.45256(12) 0.0257(3) Uani 1 d . . . H13 H 0.380(2) 0.1837(14) 0.5079(14) 0.028(4) Uiso 1 d . . . C14 C 0.1985(2) 0.31215(13) 0.51049(12) 0.0304(3) Uani 1 d . . . C15 C 0.2699(3) 0.52408(16) 0.5800(2) 0.0543(5) Uani 1 d . . . H15A H 0.184(4) 0.542(3) 0.523(3) 0.098(9) Uiso 1 d . . . H15B H 0.389(4) 0.571(2) 0.607(2) 0.079(8) Uiso 1 d . . . H15C H 0.185(4) 0.525(2) 0.639(2) 0.078(8) Uiso 1 d . . . C16 C 0.1951(2) 0.04232(13) 0.15044(11) 0.0282(3) Uani 1 d . . . C17 C 0.3352(2) -0.03166(16) 0.09348(13) 0.0357(4) Uani 1 d . . . H17 H 0.469(3) 0.0013(16) 0.1004(15) 0.042(5) Uiso 1 d . . . C18 C 0.2782(3) -0.15204(17) 0.02904(14) 0.0427(4) Uani 1 d . . . H18 H 0.376(3) -0.2015(18) -0.0087(17) 0.054(6) Uiso 1 d . . . C19 C 0.0856(3) -0.20003(15) 0.02004(13) 0.0413(4) Uani 1 d . . . C20 C -0.0531(3) -0.12381(15) 0.07376(13) 0.0367(4) Uani 1 d . . . H20 H -0.188(3) -0.1536(16) 0.0641(15) 0.040(5) Uiso 1 d . . . C21 C 0.0007(2) -0.00266(14) 0.13905(12) 0.0313(3) Uani 1 d . . . H21 H -0.097(3) 0.0495(17) 0.1770(16) 0.044(5) Uiso 1 d . . . C22 C 0.0258(5) -0.33320(19) -0.0459(2) 0.0655(6) Uani 1 d . . . H22A H 0.054(4) -0.354(3) -0.120(3) 0.098(10) Uiso 1 d . . . H22B H -0.113(6) -0.353(3) -0.049(3) 0.142(15) Uiso 1 d . . . H22C H 0.102(4) -0.383(3) -0.014(3) 0.105(10) Uiso 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 S1 0.0331(2) 0.02976(19) 0.03030(19) 0.01445(15) 0.00650(14) 0.00233(14) O1 0.0395(6) 0.0359(6) 0.0383(6) 0.0129(5) 0.0024(5) 0.0113(5) O2 0.0550(8) 0.0464(7) 0.0447(7) 0.0258(6) 0.0135(6) -0.0061(6) O3 0.0345(6) 0.0350(6) 0.0569(7) 0.0127(5) 0.0198(5) 0.0057(5) O4 0.0348(6) 0.0271(5) 0.0513(7) 0.0049(5) 0.0103(5) -0.0033(4) N1 0.0197(6) 0.0312(6) 0.0297(6) 0.0119(5) 0.0058(4) 0.0000(4) C1 0.0188(7) 0.0339(8) 0.0432(9) 0.0135(7) 0.0079(6) -0.0020(6) C2 0.0168(6) 0.0393(9) 0.0394(8) 0.0164(7) 0.0063(6) 0.0017(6) C3 0.0214(7) 0.0406(9) 0.0352(8) 0.0174(7) 0.0054(6) 0.0045(6) C4 0.0329(8) 0.0337(8) 0.0323(8) 0.0156(6) 0.0025(6) 0.0072(6) C5 0.0434(10) 0.0450(10) 0.0575(11) 0.0246(9) 0.0155(8) 0.0177(8) C6 0.0633(13) 0.0406(10) 0.0743(14) 0.0206(10) 0.0210(11) 0.0258(9) C7 0.0641(13) 0.0312(9) 0.0705(14) 0.0164(9) 0.0047(10) 0.0073(9) C8 0.0421(10) 0.0335(8) 0.0531(10) 0.0171(8) 0.0022(8) 0.0010(7) C9 0.0322(8) 0.0301(7) 0.0297(7) 0.0122(6) 0.0003(6) 0.0035(6) C10 0.0247(7) 0.0313(8) 0.0329(7) 0.0137(6) 0.0031(6) -0.0028(6) C11 0.0219(7) 0.0323(8) 0.0325(7) 0.0143(6) 0.0058(5) -0.0040(6) C12 0.0222(7) 0.0293(7) 0.0342(8) 0.0113(6) 0.0093(6) 0.0003(5) C13 0.0208(7) 0.0296(7) 0.0267(7) 0.0106(6) 0.0045(5) -0.0003(5) C14 0.0272(7) 0.0311(8) 0.0313(7) 0.0100(6) 0.0045(6) -0.0001(6) C15 0.0500(12) 0.0265(9) 0.0757(15) 0.0063(9) 0.0125(11) -0.0010(8) C16 0.0321(8) 0.0319(7) 0.0223(7) 0.0117(6) 0.0045(5) 0.0049(6) C17 0.0335(8) 0.0479(9) 0.0281(8) 0.0152(7) 0.0089(6) 0.0102(7) C18 0.0505(10) 0.0476(10) 0.0288(8) 0.0098(7) 0.0088(7) 0.0223(8) C19 0.0560(11) 0.0360(9) 0.0275(8) 0.0083(7) -0.0035(7) 0.0088(8) C20 0.0387(9) 0.0401(9) 0.0297(8) 0.0130(7) -0.0013(6) -0.0016(7) C21 0.0312(8) 0.0370(8) 0.0254(7) 0.0107(6) 0.0051(6) 0.0053(6) C22 0.0936(19) 0.0353(11) 0.0526(13) 0.0027(9) -0.0083(12) 0.0096(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4294(11) . Y S1 O2 1.4301(11) . Y S1 N1 1.6324(12) . Y S1 C16 1.7620(15) . Y O3 C14 1.1985(18) . Y O4 C14 1.3246(18) . Y O4 C15 1.451(2) . Y N1 C13 1.4716(17) . Y N1 C1 1.4774(18) . Y C1 C2 1.466(2) . Y C2 C3 1.190(2) . Y C3 C4 1.433(2) . Y C4 C5 1.392(2) . Y C4 C9 1.417(2) . Y C5 C6 1.385(3) . Y C6 C7 1.376(3) . Y C7 C8 1.381(3) . Y C8 C9 1.392(2) . Y C9 C10 1.432(2) . Y C10 C11 1.192(2) . Y C11 C12 1.457(2) . Y C12 C13 1.5364(19) . Y C13 C14 1.528(2) . Y C16 C21 1.380(2) . Y C16 C17 1.392(2) . Y C17 C18 1.381(2) . Y C18 C19 1.384(3) . Y C19 C20 1.384(2) . Y C19 C22 1.512(3) . Y C20 C21 1.386(2) . Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 120.63(7) . . Y O1 S1 N1 105.59(6) . . Y O2 S1 N1 106.59(7) . . Y O1 S1 C16 107.93(7) . . Y O2 S1 C16 107.49(7) . . Y N1 S1 C16 108.07(7) . . Y C14 O4 C15 116.40(13) . . Y C13 N1 C1 118.37(12) . . Y C13 N1 S1 120.34(9) . . Y C1 N1 S1 120.38(10) . . Y C2 C1 N1 112.00(12) . . Y C3 C2 C1 171.78(15) . . Y C2 C3 C4 166.01(15) . . Y C5 C4 C9 119.77(15) . . Y C5 C4 C3 123.70(15) . . Y C9 C4 C3 116.53(13) . . Y C6 C5 C4 119.39(18) . . Y C7 C6 C5 120.97(18) . . Y C6 C7 C8 120.56(18) . . Y C7 C8 C9 119.91(17) . . Y C8 C9 C4 119.41(15) . . Y C8 C9 C10 123.81(14) . . Y C4 C9 C10 116.77(13) . . Y C11 C10 C9 165.94(15) . . Y C10 C11 C12 177.03(14) . . Y C11 C12 C13 113.37(12) . . Y N1 C13 C14 111.43(11) . . Y N1 C13 C12 117.03(12) . . Y C14 C13 C12 109.02(11) . . Y O3 C14 O4 125.09(14) . . Y O3 C14 C13 123.97(13) . . Y O4 C14 C13 110.88(12) . . Y C21 C16 C17 120.54(15) . . Y C21 C16 S1 119.97(11) . . Y C17 C16 S1 119.44(12) . . Y C18 C17 C16 118.91(16) . . Y C17 C18 C19 121.41(15) . . Y C20 C19 C18 118.73(16) . . Y C20 C19 C22 120.0(2) . . Y C18 C19 C22 121.31(19) . . Y C19 C20 C21 120.85(16) . . Y C16 C21 C20 119.47(15) . . Y _diffrn_reflns_theta_full 27.50 _refine_diff_density_max 0.367 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.041 data_JK56 _database_code_depnum_ccdc_archive 'CCDC 698982' _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2006-07-27 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N O4 S' _chemical_formula_weight 371.44 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 8.6566(7) _cell_length_b 12.0779(8) _cell_length_c 35.500(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3711.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used 110 _cell_measurement_theta_min 2.290 _cell_measurement_theta_max 22.000 _exptl_crystal_description 'regular needle' _exptl_crystal_colour 'translucent colourless' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS multiscan (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.6996 _exptl_absorpt_correction_T_max 0.9940 _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(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 'Nonius KappaCCD' _diffrn_measurement_method 'area detector \f and \w scan' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 30562 _diffrn_reflns_av_R_equivalents 0.1411 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 22.00 _reflns_number_total 2279 _reflns_number_gt 1648 _reflns_number_observed 1648 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; Nonius "Collect" program suite (Nonius, 1999) ; _computing_cell_refinement ? _computing_data_reduction ; Nonius "EvalCCD" program suite (Duisenberg, 1998) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), PATTY (Beurskens et al., 1987) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek, 2003) ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+5.6577P] 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 2279 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1146 _refine_ls_R_factor_gt 0.0763 _refine_ls_R_factor_obs 0.0763 _refine_ls_wR_factor_ref 0.1452 _refine_ls_wR_factor_all 0.1452 _refine_ls_wR_factor_gt 0.1329 _refine_ls_wR_factor_obs 0.1329 _refine_ls_goodness_of_fit_ref 1.224 _refine_ls_goodness_of_fit_all 1.224 _refine_ls_restrained_S_all 1.224 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.17923(16) 0.18279(11) 0.08853(4) 0.0298(4) Uani 1 d . . . O1 O 0.3397(4) 0.1637(3) 0.09581(9) 0.0336(10) Uani 1 d . . . O2 O 0.0783(4) 0.0918(3) 0.08111(9) 0.0384(10) Uani 1 d . . . N1 N 0.1084(4) 0.2502(4) 0.12398(11) 0.0282(11) Uani 1 d . . . C2 C 0.2121(5) 0.3116(4) 0.14894(13) 0.0264(13) Uani 1 d . . . H2 H 0.3160 0.3054 0.1375 0.032 Uiso 1 calc R . . C3 C 0.1803(6) 0.4360(4) 0.15241(15) 0.0345(14) Uani 1 d . . . H3A H 0.2733 0.4716 0.1624 0.041 Uiso 1 calc R . . H3B H 0.1630 0.4657 0.1271 0.041 Uiso 1 calc R . . C4 C 0.0493(8) 0.4677(5) 0.17609(17) 0.0401(16) Uani 1 d . . . C5 C -0.0581(8) 0.4947(5) 0.19458(18) 0.0503(18) Uani 1 d . . . C6 C -0.1924(9) 0.5239(6) 0.2158(2) 0.071(2) Uani 1 d . . . H6 H -0.1822 0.5718 0.2365 0.085 Uiso 1 calc R . . C7 C -0.3307(9) 0.4853(6) 0.2069(2) 0.070(2) Uani 1 d . . . H7 H -0.4170 0.5095 0.2207 0.084 Uiso 1 calc R . . C8 C -0.3524(7) 0.4089(6) 0.1774(2) 0.0543(19) Uani 1 d . . . C9 C -0.3527(7) 0.3419(6) 0.1535(2) 0.058(2) Uani 1 d . . . C10A C -0.3331(11) 0.2768(12) 0.1194(3) 0.051(4) Uani 0.666(14) d P A 1 H10A H -0.3995 0.3063 0.0994 0.062 Uiso 0.666(14) calc PR A 1 H10B H -0.3634 0.1999 0.1242 0.062 Uiso 0.666(14) calc PR A 1 C11A C -0.1630(11) 0.2809(8) 0.1067(2) 0.040(3) Uani 0.666(14) d P A 1 H11A H -0.1521 0.2398 0.0831 0.048 Uiso 0.666(14) calc PR A 1 H11B H -0.1340 0.3581 0.1018 0.048 Uiso 0.666(14) calc PR A 1 C12A C -0.0550(11) 0.2330(9) 0.1355(3) 0.029(3) Uani 0.666(14) d P A 1 H12A H -0.0730 0.2685 0.1600 0.035 Uiso 0.666(14) calc PR A 1 H12B H -0.0752 0.1536 0.1383 0.035 Uiso 0.666(14) calc PR A 1 C10B C -0.326(3) 0.2231(18) 0.1352(7) 0.043(7) Uiso 0.334(14) d P A 2 H10C H -0.3870 0.1683 0.1491 0.052 Uiso 0.334(14) calc PR A 2 H10D H -0.3626 0.2241 0.1091 0.052 Uiso 0.334(14) calc PR A 2 C11B C -0.158(2) 0.1882(15) 0.1357(5) 0.037(6) Uiso 0.334(14) d P A 2 H11C H -0.1265 0.1734 0.1617 0.044 Uiso 0.334(14) calc PR A 2 H11D H -0.1467 0.1195 0.1212 0.044 Uiso 0.334(14) calc PR A 2 C12B C -0.056(2) 0.2758(16) 0.1191(6) 0.024(7) Uiso 0.334(14) d P A 2 H12C H -0.0788 0.2831 0.0922 0.029 Uiso 0.334(14) calc PR A 2 H12D H -0.0789 0.3469 0.1312 0.029 Uiso 0.334(14) calc PR A 2 C13 C 0.2244(6) 0.2557(5) 0.18742(14) 0.0281(14) Uani 1 d . . . O3 O 0.1603(4) 0.1733(3) 0.19713(10) 0.0438(11) Uani 1 d . . . O4 O 0.3246(4) 0.3121(3) 0.20812(9) 0.0419(10) Uani 1 d . . . C14 C 0.3698(7) 0.2620(5) 0.24354(16) 0.0579(19) Uani 1 d . . . H14A H 0.2832 0.2637 0.2609 0.087 Uiso 1 calc R . . H14B H 0.4557 0.3029 0.2542 0.087 Uiso 1 calc R . . H14C H 0.4007 0.1858 0.2392 0.087 Uiso 1 calc R . . C21 C 0.1710(6) 0.2721(4) 0.04925(14) 0.0271(13) Uani 1 d . . . C22 C 0.2614(6) 0.3659(4) 0.04809(15) 0.0351(15) Uani 1 d . . . H22 H 0.3248 0.3839 0.0687 0.042 Uiso 1 calc R . . C23 C 0.2593(7) 0.4336(5) 0.01684(14) 0.0360(14) Uani 1 d . . . H23 H 0.3216 0.4973 0.0162 0.043 Uiso 1 calc R . . C24 C 0.1647(7) 0.4078(5) -0.01385(15) 0.0374(15) Uani 1 d . . . C25 C 0.0739(7) 0.3148(5) -0.01229(15) 0.0407(16) Uani 1 d . . . H25 H 0.0098 0.2970 -0.0328 0.049 Uiso 1 calc R . . C26 C 0.0754(6) 0.2472(5) 0.01908(15) 0.0346(15) Uani 1 d . . . H26 H 0.0117 0.1842 0.0200 0.042 Uiso 1 calc R . . C27 C 0.1658(7) 0.4832(5) -0.04781(15) 0.0561(18) Uani 1 d . . . H27A H 0.0860 0.4602 -0.0653 0.084 Uiso 1 calc R . . H27B H 0.2658 0.4792 -0.0601 0.084 Uiso 1 calc R . . H27C H 0.1464 0.5588 -0.0398 0.084 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0334(8) 0.0308(8) 0.0251(8) -0.0017(7) 0.0003(7) 0.0027(8) O1 0.028(2) 0.044(3) 0.029(2) 0.0071(19) 0.0028(17) 0.0103(19) O2 0.046(2) 0.030(2) 0.039(2) -0.0095(19) 0.0012(19) -0.011(2) N1 0.022(2) 0.037(3) 0.026(3) -0.008(2) 0.003(2) -0.002(2) C2 0.022(3) 0.035(3) 0.022(3) -0.001(3) 0.003(2) -0.003(3) C3 0.044(3) 0.026(3) 0.033(3) 0.005(3) -0.001(3) -0.003(3) C4 0.051(4) 0.024(4) 0.045(4) -0.002(3) -0.008(4) 0.008(3) C5 0.057(5) 0.038(4) 0.056(5) -0.016(4) -0.011(4) 0.010(4) C6 0.062(5) 0.070(5) 0.082(6) -0.036(4) -0.001(5) 0.023(5) C7 0.058(5) 0.081(6) 0.071(5) -0.026(5) 0.014(5) 0.022(5) C8 0.038(4) 0.076(5) 0.049(5) -0.004(4) 0.015(4) 0.012(4) C9 0.029(4) 0.088(6) 0.058(5) -0.014(5) 0.005(4) 0.000(4) C10A 0.037(6) 0.072(10) 0.045(7) -0.021(7) -0.010(5) -0.002(6) C11A 0.027(6) 0.066(7) 0.027(5) -0.008(5) 0.000(4) -0.004(5) C12A 0.036(7) 0.029(6) 0.022(5) 0.000(5) -0.005(5) 0.002(5) C13 0.028(3) 0.032(4) 0.024(3) -0.007(3) 0.003(3) 0.001(3) O3 0.055(3) 0.041(3) 0.035(2) 0.008(2) 0.000(2) -0.017(2) O4 0.053(2) 0.043(2) 0.030(2) 0.010(2) -0.013(2) -0.011(2) C14 0.075(5) 0.062(5) 0.037(4) 0.016(4) -0.020(3) -0.011(4) C21 0.027(3) 0.028(3) 0.026(3) -0.004(3) -0.004(3) 0.005(3) C22 0.046(4) 0.034(4) 0.025(3) -0.012(3) -0.004(3) -0.007(3) C23 0.050(4) 0.027(3) 0.031(3) 0.000(3) 0.005(3) -0.002(3) C24 0.051(4) 0.038(4) 0.023(3) -0.003(3) -0.003(3) 0.015(3) C25 0.045(4) 0.053(4) 0.025(3) -0.009(4) -0.010(3) 0.003(4) C26 0.037(4) 0.034(4) 0.033(4) -0.009(3) -0.001(3) 0.003(3) C27 0.081(5) 0.053(4) 0.034(4) 0.004(3) 0.004(4) 0.015(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 S1 O2 1.429(4) . Y S1 O1 1.432(3) . Y S1 N1 1.619(4) . Y S1 C21 1.765(5) . Y N1 C2 1.463(6) . Y N1 C12B 1.47(2) . Y N1 C12A 1.487(11) . Y C2 C13 1.527(7) . Y C2 C3 1.533(7) . Y C3 C4 1.463(8) . Y C4 C5 1.184(8) . Y C5 C6 1.429(9) . Y C6 C7 1.323(9) . Y C7 C8 1.410(10) . Y C8 C9 1.172(9) . Y C9 C10A 1.452(11) . Y C9 C10B 1.59(2) . Y C10A C11A 1.540(13) . Y C11A C12A 1.503(14) . Y C10B C11B 1.51(3) . Y C11B C12B 1.50(3) . Y C13 O3 1.191(6) . Y C13 O4 1.325(6) . Y O4 C14 1.449(6) . Y C21 C22 1.378(7) . Y C21 C26 1.386(7) . Y C22 C23 1.378(7) . Y C23 C24 1.398(7) . Y C24 C25 1.371(8) . Y C24 C27 1.511(7) . Y C25 C26 1.381(7) . Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 120.2(2) . . Y O2 S1 N1 107.4(2) . . Y O1 S1 N1 107.9(2) . . Y O2 S1 C21 107.5(2) . . Y O1 S1 C21 106.3(2) . . Y N1 S1 C21 106.9(2) . . Y C2 N1 C12B 124.0(8) . . Y C2 N1 C12A 119.2(5) . . Y C2 N1 S1 119.6(3) . . Y C12B N1 S1 112.5(8) . . Y C12A N1 S1 120.3(4) . . Y N1 C2 C13 111.2(4) . . Y N1 C2 C3 115.8(4) . . Y C13 C2 C3 111.9(4) . . Y C4 C3 C2 116.3(4) . . Y C5 C4 C3 178.5(6) . . Y C4 C5 C6 177.2(7) . . Y C7 C6 C5 121.6(7) . . Y C6 C7 C8 121.9(7) . . Y C9 C8 C7 172.1(7) . . Y C8 C9 C10A 167.4(9) . . Y C8 C9 C10B 156.4(11) . . Y C9 C10A C11A 109.8(7) . . Y C12A C11A C10A 112.5(8) . . Y N1 C12A C11A 110.5(8) . . Y C11B C10B C9 112.9(15) . . Y C12B C11B C10B 111.5(16) . . Y N1 C12B C11B 112.3(16) . . Y O3 C13 O4 125.0(5) . . Y O3 C13 C2 126.6(5) . . Y O4 C13 C2 108.3(5) . . Y C13 O4 C14 116.3(4) . . Y C22 C21 C26 119.6(5) . . Y C22 C21 S1 120.3(4) . . Y C26 C21 S1 120.1(4) . . Y C21 C22 C23 120.3(5) . . Y C22 C23 C24 120.2(5) . . Y C25 C24 C23 119.1(5) . . Y C25 C24 C27 122.0(5) . . Y C23 C24 C27 118.9(6) . . Y C24 C25 C26 120.7(5) . . Y C25 C26 C21 120.0(6) . . Y _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 22.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.225 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.055 data_JK93 _database_code_depnum_ccdc_archive 'CCDC 698983' _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2006-07-27 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H23 N O4 S' _chemical_formula_weight 421.49 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4021(5) _cell_length_b 11.9570(9) _cell_length_c 12.0405(8) _cell_angle_alpha 69.128(6) _cell_angle_beta 70.351(5) _cell_angle_gamma 84.942(5) _cell_volume 1063.76(12) _cell_formula_units_Z 2 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used 115 _cell_measurement_theta_min 2.580 _cell_measurement_theta_max 27.500 _exptl_crystal_description 'rather regular large fragment' _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.33 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS multiscan (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.8059 _exptl_absorpt_correction_T_max 0.9422 _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(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 'Nonius KappaCCD' _diffrn_measurement_method 'area detector \f and \w scan' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 27752 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0156 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4862 _reflns_number_gt 4028 _reflns_number_observed 4028 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; Nonius "Collect" program suite (Nonius, 1999) ; _computing_cell_refinement ? _computing_data_reduction ; Nonius "EvalCCD" program suite (Duisenberg, 1998) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), PATTY (Beurskens et al., 1987) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek, 2003) ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.4145P] 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 4862 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0364 _refine_ls_R_factor_obs 0.0364 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_all 0.0967 _refine_ls_wR_factor_gt 0.0888 _refine_ls_wR_factor_obs 0.0888 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_goodness_of_fit_all 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.09877(4) 0.25211(3) 0.13884(3) 0.02866(10) Uani 1 d . . . O1 O 1.24894(13) 0.19086(11) 0.15118(10) 0.0399(3) Uani 1 d . . . O2 O 1.10912(14) 0.36109(10) 0.03673(9) 0.0373(3) Uani 1 d . . . O3 O 0.78260(12) 0.03935(9) 0.54747(9) 0.0322(2) Uani 1 d . . . O4 O 0.68950(13) 0.16261(9) 0.39477(10) 0.0341(2) Uani 1 d . . . N1 N 1.00528(14) 0.28246(10) 0.26634(10) 0.0252(2) Uani 1 d . . . C1 C 0.90197(17) 0.38908(12) 0.26017(13) 0.0264(3) Uani 1 d . . . H1A H 0.8128 0.3750 0.3415 0.032 Uiso 1 calc R . . H1B H 0.8475 0.4023 0.1964 0.032 Uiso 1 calc R . . C2 C 1.0064(2) 0.49992(13) 0.22802(15) 0.0346(3) Uani 1 d . . . H2A H 1.0843 0.5211 0.1415 0.041 Uiso 1 calc R . . H2B H 1.0740 0.4829 0.2841 0.041 Uiso 1 calc R . . C3 C 0.8951(2) 0.60564(13) 0.24086(15) 0.0431(4) Uani 1 d . . . H3A H 0.9666 0.6784 0.2074 0.052 Uiso 1 calc R . . H3B H 0.8195 0.6178 0.1911 0.052 Uiso 1 calc R . . C4 C 0.7946(2) 0.58548(13) 0.37178(16) 0.0375(3) Uani 1 d . . . C5 C 0.7219(2) 0.55890(14) 0.48140(16) 0.0359(3) Uani 1 d . . . C6 C 0.65069(18) 0.51313(15) 0.61537(15) 0.0345(3) Uani 1 d . . . C7 C 0.5501(2) 0.58094(18) 0.68352(18) 0.0461(4) Uani 1 d . . . H7 H 0.5240 0.6592 0.6411 0.055 Uiso 1 calc R . . C8 C 0.4884(2) 0.5338(2) 0.81314(19) 0.0548(5) Uani 1 d . . . H8 H 0.4223 0.5810 0.8584 0.066 Uiso 1 calc R . . C9 C 0.5221(2) 0.4190(2) 0.87682(18) 0.0518(5) Uani 1 d . . . H9 H 0.4776 0.3874 0.9651 0.062 Uiso 1 calc R . . C10 C 0.6213(2) 0.35031(17) 0.81126(16) 0.0433(4) Uani 1 d . . . H10 H 0.6442 0.2716 0.8550 0.052 Uiso 1 calc R . . C11 C 0.68809(19) 0.39649(14) 0.68044(14) 0.0336(3) Uani 1 d . . . C12 C 0.8007(2) 0.32802(13) 0.61298(14) 0.0333(3) Uani 1 d . . . C13 C 0.90235(19) 0.27746(13) 0.55392(14) 0.0321(3) Uani 1 d . . . C14 C 1.02937(18) 0.21572(13) 0.48205(13) 0.0299(3) Uani 1 d . . . H14A H 1.0555 0.1416 0.5411 0.036 Uiso 1 calc R . . H14B H 1.1331 0.2663 0.4379 0.036 Uiso 1 calc R . . C15 C 0.97842(16) 0.18400(11) 0.38487(12) 0.0235(3) Uani 1 d . . . H15 H 1.0538 0.1201 0.3656 0.028 Uiso 1 calc R . . C16 C 0.79894(16) 0.13053(11) 0.44036(12) 0.0242(3) Uani 1 d . . . C17 C 0.6194(2) -0.02297(17) 0.60851(17) 0.0492(5) Uani 1 d . . . H17A H 0.5315 0.0342 0.6200 0.074 Uiso 1 calc R . . H17B H 0.6156 -0.0812 0.6898 0.074 Uiso 1 calc R . . H17C H 0.6016 -0.0637 0.5567 0.074 Uiso 1 calc R . . C18 C 0.96552(19) 0.14908(13) 0.13500(13) 0.0310(3) Uani 1 d . . . C19 C 0.9889(2) 0.02748(15) 0.18332(18) 0.0451(4) Uani 1 d . . . H19 H 1.0802 -0.0002 0.2132 0.054 Uiso 1 calc R . . C20 C 0.8779(3) -0.05227(17) 0.1873(2) 0.0571(5) Uani 1 d . . . H20 H 0.8931 -0.1348 0.2213 0.069 Uiso 1 calc R . . C21 C 0.7436(3) -0.01402(18) 0.14217(18) 0.0519(5) Uani 1 d . . . C22 C 0.7219(2) 0.10796(18) 0.09467(16) 0.0465(4) Uani 1 d . . . H22 H 0.6306 0.1355 0.0648 0.056 Uiso 1 calc R . . C23 C 0.8318(2) 0.19010(15) 0.09029(14) 0.0372(3) Uani 1 d . . . H23 H 0.8159 0.2727 0.0574 0.045 Uiso 1 calc R . . C24 C 0.6249(3) -0.1030(2) 0.1450(3) 0.0802(8) Uani 1 d . . . H24A H 0.5175 -0.0665 0.1438 0.120 Uiso 1 calc R . . H24B H 0.6073 -0.1727 0.2210 0.120 Uiso 1 calc R . . H24C H 0.6735 -0.1272 0.0721 0.120 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.02733(18) 0.03136(19) 0.02303(17) -0.00732(14) -0.00463(13) -0.00158(13) O1 0.0287(5) 0.0517(7) 0.0347(6) -0.0154(5) -0.0056(4) 0.0059(5) O2 0.0421(6) 0.0369(6) 0.0230(5) -0.0023(4) -0.0047(4) -0.0074(5) O3 0.0252(5) 0.0319(5) 0.0290(5) 0.0021(4) -0.0081(4) -0.0052(4) O4 0.0304(5) 0.0324(5) 0.0370(6) -0.0027(4) -0.0163(4) -0.0048(4) N1 0.0279(6) 0.0228(5) 0.0219(5) -0.0054(4) -0.0066(4) -0.0013(4) C1 0.0283(7) 0.0234(6) 0.0276(7) -0.0070(5) -0.0115(5) 0.0004(5) C2 0.0405(8) 0.0247(7) 0.0332(8) -0.0052(6) -0.0088(6) -0.0068(6) C3 0.0682(11) 0.0230(7) 0.0337(8) -0.0057(6) -0.0160(8) 0.0019(7) C4 0.0487(9) 0.0282(7) 0.0405(9) -0.0125(7) -0.0207(7) 0.0039(6) C5 0.0379(8) 0.0339(8) 0.0435(9) -0.0172(7) -0.0188(7) 0.0029(6) C6 0.0275(7) 0.0454(9) 0.0386(8) -0.0217(7) -0.0123(6) -0.0024(6) C7 0.0323(8) 0.0613(11) 0.0578(11) -0.0346(9) -0.0179(8) 0.0090(7) C8 0.0283(8) 0.0957(16) 0.0568(12) -0.0516(12) -0.0089(8) 0.0078(9) C9 0.0338(9) 0.0866(15) 0.0383(9) -0.0317(10) -0.0016(7) -0.0131(9) C10 0.0426(9) 0.0542(10) 0.0332(8) -0.0159(7) -0.0075(7) -0.0165(8) C11 0.0316(7) 0.0417(8) 0.0320(8) -0.0173(7) -0.0087(6) -0.0087(6) C12 0.0415(8) 0.0335(8) 0.0281(7) -0.0103(6) -0.0141(6) -0.0061(6) C13 0.0413(8) 0.0309(7) 0.0272(7) -0.0081(6) -0.0159(6) -0.0050(6) C14 0.0312(7) 0.0314(7) 0.0294(7) -0.0084(6) -0.0141(6) -0.0021(6) C15 0.0242(6) 0.0214(6) 0.0231(6) -0.0052(5) -0.0078(5) -0.0006(5) C16 0.0266(6) 0.0210(6) 0.0245(6) -0.0076(5) -0.0078(5) -0.0004(5) C17 0.0295(8) 0.0514(10) 0.0423(9) 0.0132(8) -0.0094(7) -0.0134(7) C18 0.0364(7) 0.0316(7) 0.0247(7) -0.0126(6) -0.0060(6) -0.0007(6) C19 0.0526(10) 0.0355(9) 0.0521(10) -0.0224(8) -0.0170(8) 0.0085(7) C20 0.0722(13) 0.0343(9) 0.0693(13) -0.0282(9) -0.0173(11) 0.0001(9) C21 0.0617(12) 0.0525(11) 0.0454(10) -0.0283(9) -0.0060(9) -0.0159(9) C22 0.0470(10) 0.0610(11) 0.0339(9) -0.0164(8) -0.0127(7) -0.0122(8) C23 0.0424(8) 0.0381(8) 0.0292(8) -0.0078(6) -0.0122(6) -0.0038(7) C24 0.0892(17) 0.0786(16) 0.0856(18) -0.0475(14) -0.0156(14) -0.0321(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4225(11) . Y S1 O1 1.4269(11) . Y S1 N1 1.6253(12) . Y S1 C18 1.7583(15) . Y O3 C16 1.3327(16) . Y O3 C17 1.4448(17) . Y O4 C16 1.1921(16) . Y N1 C15 1.4515(16) . Y N1 C1 1.4714(17) . Y C1 C2 1.5122(19) . Y C2 C3 1.526(2) . Y C3 C4 1.458(2) . Y C4 C5 1.187(2) . Y C5 C6 1.428(2) . Y C6 C7 1.390(2) . Y C6 C11 1.403(2) . Y C7 C8 1.379(3) . Y C8 C9 1.371(3) . Y C9 C10 1.375(3) . Y C10 C11 1.393(2) . Y C11 C12 1.430(2) . Y C12 C13 1.187(2) . Y C13 C14 1.459(2) . Y C14 C15 1.5420(18) . Y C15 C16 1.5223(18) . Y C18 C23 1.383(2) . Y C18 C19 1.384(2) . Y C19 C20 1.370(3) . Y C20 C21 1.386(3) . Y C21 C22 1.384(3) . Y C21 C24 1.505(3) . Y C22 C23 1.382(2) . Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 120.02(7) . . Y O2 S1 N1 106.24(6) . . Y O1 S1 N1 107.75(6) . . Y O2 S1 C18 108.76(7) . . Y O1 S1 C18 106.46(7) . . Y N1 S1 C18 106.98(6) . . Y C16 O3 C17 115.63(11) . . Y C15 N1 C1 120.31(11) . . Y C15 N1 S1 116.77(9) . . Y C1 N1 S1 119.39(9) . . Y N1 C1 C2 112.02(11) . . Y C1 C2 C3 111.60(13) . . Y C4 C3 C2 111.38(13) . . Y C5 C4 C3 173.33(17) . . Y C4 C5 C6 171.79(17) . . Y C7 C6 C11 118.97(15) . . Y C7 C6 C5 122.49(16) . . Y C11 C6 C5 118.51(14) . . Y C8 C7 C6 120.28(19) . . Y C9 C8 C7 120.84(17) . . Y C8 C9 C10 119.85(17) . . Y C9 C10 C11 120.51(18) . . Y C10 C11 C6 119.53(15) . . Y C10 C11 C12 120.43(15) . . Y C6 C11 C12 119.97(14) . . Y C13 C12 C11 175.42(16) . . Y C12 C13 C14 179.09(15) . . Y C13 C14 C15 115.18(12) . . Y N1 C15 C16 112.24(10) . . Y N1 C15 C14 113.53(11) . . Y C16 C15 C14 111.34(11) . . Y O4 C16 O3 124.51(12) . . Y O4 C16 C15 125.88(12) . . Y O3 C16 C15 109.59(11) . . Y C23 C18 C19 120.41(15) . . Y C23 C18 S1 119.57(12) . . Y C19 C18 S1 119.91(13) . . Y C20 C19 C18 119.47(17) . . Y C19 C20 C21 121.50(18) . . Y C22 C21 C20 118.16(16) . . Y C22 C21 C24 121.1(2) . . Y C20 C21 C24 120.7(2) . . Y C23 C22 C21 121.36(17) . . Y C22 C23 C18 119.08(16) . . Y _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.238 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.045 data_JK105 _database_code_depnum_ccdc_archive 'CCDC 698984' _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2006-07-27 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H21 N O4 S' _chemical_formula_weight 407.47 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.1942(12) _cell_length_b 9.7320(7) _cell_length_c 13.0079(13) _cell_angle_alpha 90.00 _cell_angle_beta 104.996(9) _cell_angle_gamma 90.00 _cell_volume 1002.00(19) _cell_formula_units_Z 2 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used 43 _cell_measurement_theta_min 2.570 _cell_measurement_theta_max 25.000 _exptl_crystal_description 'rather regular fragment' _exptl_crystal_colour 'translucent colourless' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS multiscan (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.7650 _exptl_absorpt_correction_T_max 0.9924 _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(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 'Nonius KappaCCD' _diffrn_measurement_method 'area detector \f and \w scan' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 13482 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3516 _reflns_number_gt 2608 _reflns_number_observed 2608 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; Nonius "Collect" program suite (Nonius, 1999) ; _computing_cell_refinement ? _computing_data_reduction ; Nonius "EvalCCD" program suite (Duisenberg, 1998) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), PATTY (Beurskens et al., 1987) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek, 2003) ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0202P)^2^+0.4542P] 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 ? _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack 0.04(3) _refine_ls_abs_structure_details ; The absolute configuration assignment was based on 1638 Friedel pairs used to calculate the Flack parameter. Flack H.D.(1983), Acta Cryst. A39, 876-881 ; _refine_ls_number_reflns 3516 _refine_ls_number_parameters 264 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0523 _refine_ls_R_factor_obs 0.0523 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_all 0.0833 _refine_ls_wR_factor_gt 0.0752 _refine_ls_wR_factor_obs 0.0752 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_goodness_of_fit_all 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.16966(11) 0.00912(9) 0.12767(7) 0.0335(2) Uani 1 d . . . N1 N 0.3208(3) 0.1204(3) 0.1725(2) 0.0268(7) Uani 1 d . . . C2 C 0.2803(4) 0.2663(3) 0.1485(3) 0.0305(9) Uani 1 d . . . H2A H 0.3090 0.2916 0.0823 0.037 Uiso 1 calc R . . H2B H 0.1590 0.2813 0.1385 0.037 Uiso 1 calc R . . C3 C 0.3753(4) 0.3517(3) 0.2355(3) 0.0285(8) Uani 1 d . . . C4 C 0.4625(4) 0.4136(4) 0.3072(3) 0.0294(8) Uani 1 d . . . C5 C 0.5735(4) 0.4787(4) 0.3977(3) 0.0309(9) Uani 1 d . . . C6 C 0.5526(5) 0.6148(4) 0.4208(3) 0.0401(10) Uani 1 d . . . H6 H 0.4660 0.6670 0.3765 0.048 Uiso 1 calc R . . C7 C 0.6590(5) 0.6736(4) 0.5091(3) 0.0501(11) Uani 1 d . . . H7 H 0.6461 0.7668 0.5243 0.060 Uiso 1 calc R . . C8 C 0.7846(5) 0.5970(5) 0.5757(3) 0.0477(11) Uani 1 d . . . H8 H 0.8557 0.6376 0.6365 0.057 Uiso 1 calc R . . C9 C 0.8055(5) 0.4618(4) 0.5531(3) 0.0435(11) Uani 1 d . . . H9 H 0.8904 0.4100 0.5994 0.052 Uiso 1 calc R . . C10 C 0.7031(4) 0.3996(4) 0.4627(3) 0.0340(9) Uani 1 d . . . C11 C 0.7307(4) 0.2622(4) 0.4319(3) 0.0369(10) Uani 1 d . . . C12 C 0.7446(5) 0.1514(4) 0.3982(3) 0.0388(10) Uani 1 d . . . C13 C 0.7396(4) 0.0163(4) 0.3479(3) 0.0404(9) Uani 1 d . . . H13A H 0.7805 -0.0536 0.4027 0.048 Uiso 1 calc R . . H13B H 0.8144 0.0163 0.3000 0.048 Uiso 1 calc R . . C14 C 0.5604(4) -0.0191(3) 0.2851(3) 0.0347(9) Uani 1 d . . . H14A H 0.4846 -0.0151 0.3323 0.042 Uiso 1 calc R . . H14B H 0.5578 -0.1129 0.2574 0.042 Uiso 1 calc R . . C15 C 0.4990(4) 0.0816(3) 0.1924(3) 0.0310(9) Uani 1 d . . . H15 H 0.5633 0.1674 0.2150 0.037 Uiso 1 calc R . . C16 C 0.5460(4) 0.0363(4) 0.0909(3) 0.0317(9) Uani 1 d . . . O17 O 0.5100(3) 0.1358(2) 0.02017(18) 0.0401(7) Uani 1 d . . . O18 O 0.6061(4) -0.0722(3) 0.0789(2) 0.0514(8) Uani 1 d . . . C19 C 0.5374(5) 0.1059(4) -0.0824(3) 0.0523(12) Uani 1 d . . . H19A H 0.6549 0.0814 -0.0740 0.078 Uiso 1 calc R . . H19B H 0.5101 0.1863 -0.1277 0.078 Uiso 1 calc R . . H19C H 0.4658 0.0299 -0.1147 0.078 Uiso 1 calc R . . O20 O 0.0251(3) 0.0606(2) 0.15663(19) 0.0453(7) Uani 1 d . . . O21 O 0.2403(3) -0.1218(2) 0.16478(19) 0.0422(7) Uani 1 d . . . C22 C 0.1195(4) 0.0073(4) -0.0125(2) 0.0284(7) Uani 1 d . . . C23 C 0.0170(5) 0.1072(4) -0.0682(3) 0.0411(10) Uani 1 d . . . H23 H -0.0227 0.1779 -0.0318 0.049 Uiso 1 calc R . . C24 C -0.0281(5) 0.1046(4) -0.1772(3) 0.0419(10) Uani 1 d . . . H24 H -0.0989 0.1738 -0.2149 0.050 Uiso 1 calc R . . C25 C 0.0284(4) 0.0026(4) -0.2324(3) 0.0357(8) Uani 1 d . . . C26 C 0.1323(4) -0.0971(4) -0.1752(3) 0.0352(10) Uani 1 d . . . H26 H 0.1710 -0.1684 -0.2116 0.042 Uiso 1 calc R . . C27 C 0.1808(4) -0.0945(3) -0.0659(3) 0.0343(9) Uani 1 d . . . H27 H 0.2550 -0.1615 -0.0279 0.041 Uiso 1 calc R . . C28 C -0.0289(5) -0.0039(5) -0.3514(3) 0.0526(11) Uani 1 d . . . H28A H -0.1493 0.0144 -0.3744 0.079 Uiso 1 calc R . . H28B H -0.0060 -0.0946 -0.3752 0.079 Uiso 1 calc R . . H28C H 0.0314 0.0644 -0.3816 0.079 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0323(5) 0.0352(5) 0.0325(5) -0.0030(5) 0.0074(4) -0.0105(5) N1 0.0236(16) 0.0234(15) 0.0304(16) 0.0012(13) 0.0013(13) -0.0014(13) C2 0.030(2) 0.030(2) 0.028(2) 0.0013(17) 0.0007(17) 0.0018(17) C3 0.033(2) 0.0251(19) 0.027(2) 0.0062(17) 0.0074(18) 0.0071(18) C4 0.032(2) 0.030(2) 0.027(2) 0.0003(18) 0.0085(18) 0.0021(18) C5 0.033(2) 0.036(3) 0.026(2) -0.0060(18) 0.0114(17) -0.0119(19) C6 0.042(3) 0.039(2) 0.040(2) -0.009(2) 0.010(2) -0.009(2) C7 0.056(3) 0.052(3) 0.049(3) -0.019(2) 0.024(2) -0.013(2) C8 0.043(3) 0.067(3) 0.036(2) -0.019(2) 0.016(2) -0.018(3) C9 0.032(2) 0.068(3) 0.030(2) 0.001(2) 0.0068(19) -0.010(2) C10 0.029(2) 0.047(2) 0.027(2) -0.004(2) 0.0091(18) -0.010(2) C11 0.027(2) 0.049(3) 0.030(2) 0.004(2) -0.0002(18) -0.008(2) C12 0.029(2) 0.050(3) 0.030(2) 0.008(2) -0.0064(17) -0.002(2) C13 0.033(2) 0.044(2) 0.039(2) 0.009(2) 0.0006(17) 0.007(2) C14 0.034(2) 0.029(2) 0.039(2) 0.0043(17) 0.0052(18) 0.0027(17) C15 0.028(2) 0.0269(19) 0.036(2) -0.0022(17) 0.0044(17) -0.0065(17) C16 0.0222(19) 0.024(2) 0.046(2) -0.0069(19) 0.0037(17) -0.0109(17) O17 0.0606(18) 0.0287(14) 0.0350(15) -0.0018(13) 0.0199(13) -0.0005(13) O18 0.063(2) 0.0347(16) 0.061(2) -0.0027(15) 0.0256(16) 0.0128(15) C19 0.074(3) 0.048(3) 0.045(3) -0.008(2) 0.035(2) -0.013(2) O20 0.0330(15) 0.0611(19) 0.0462(16) -0.0109(13) 0.0182(13) -0.0131(13) O21 0.0498(18) 0.0319(15) 0.0390(16) 0.0051(12) 0.0011(13) -0.0154(14) C22 0.0252(18) 0.0244(18) 0.0322(19) -0.004(2) 0.0015(15) -0.0044(19) C23 0.042(2) 0.038(2) 0.040(2) -0.0121(19) 0.005(2) 0.008(2) C24 0.043(2) 0.038(2) 0.040(2) 0.002(2) 0.002(2) 0.015(2) C25 0.030(2) 0.043(2) 0.033(2) -0.006(2) 0.0060(16) 0.004(2) C26 0.032(2) 0.041(2) 0.033(2) -0.0093(19) 0.0078(19) 0.003(2) C27 0.034(2) 0.022(2) 0.043(3) 0.0024(18) 0.0037(19) -0.0015(18) C28 0.051(3) 0.065(3) 0.041(2) 0.001(3) 0.012(2) 0.016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O20 1.424(2) . Y S1 O21 1.431(2) . Y S1 N1 1.635(3) . Y S1 C22 1.762(3) . Y N1 C15 1.465(4) . Y N1 C2 1.473(4) . Y C2 C3 1.457(5) . Y C3 C4 1.183(4) . Y C4 C5 1.435(5) . Y C5 C6 1.379(5) . Y C5 C10 1.404(5) . Y C6 C7 1.374(5) . Y C7 C8 1.380(5) . Y C8 C9 1.368(5) . Y C9 C10 1.394(5) . Y C10 C11 1.430(5) . Y C11 C12 1.181(5) . Y C12 C13 1.464(5) . Y C13 C14 1.523(4) . Y C14 C15 1.534(4) . Y C15 C16 1.533(5) . Y C16 O18 1.192(4) . Y C16 O17 1.316(4) . Y O17 C19 1.439(4) . Y C22 C23 1.364(5) . Y C22 C27 1.378(5) . Y C23 C24 1.370(5) . Y C24 C25 1.374(5) . Y C25 C26 1.376(5) . Y C25 C28 1.498(4) . Y C26 C27 1.374(4) . Y 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 O20 S1 O21 121.05(16) . . Y O20 S1 N1 106.14(14) . . Y O21 S1 N1 105.46(15) . . Y O20 S1 C22 106.85(15) . . Y O21 S1 C22 107.82(16) . . Y N1 S1 C22 109.13(15) . . Y C15 N1 C2 116.5(3) . . Y C15 N1 S1 121.4(2) . . Y C2 N1 S1 117.0(2) . . Y C3 C2 N1 109.9(3) . . Y C4 C3 C2 174.8(4) . . Y C3 C4 C5 175.5(4) . . Y C6 C5 C10 120.8(4) . . Y C6 C5 C4 121.0(4) . . Y C10 C5 C4 118.2(3) . . Y C7 C6 C5 119.7(4) . . Y C6 C7 C8 120.5(4) . . Y C9 C8 C7 120.0(4) . . Y C8 C9 C10 121.2(4) . . Y C9 C10 C5 117.8(4) . . Y C9 C10 C11 122.6(4) . . Y C5 C10 C11 119.6(3) . . Y C12 C11 C10 174.4(4) . . Y C11 C12 C13 172.6(4) . . Y C12 C13 C14 110.8(3) . . Y C13 C14 C15 110.6(3) . . Y N1 C15 C16 112.5(3) . . Y N1 C15 C14 114.4(3) . . Y C16 C15 C14 112.9(3) . . Y O18 C16 O17 125.8(3) . . Y O18 C16 C15 124.9(3) . . Y O17 C16 C15 109.2(3) . . Y C16 O17 C19 116.1(3) . . Y C23 C22 C27 120.0(3) . . Y C23 C22 S1 119.3(3) . . Y C27 C22 S1 120.7(3) . . Y C22 C23 C24 120.0(3) . . Y C23 C24 C25 121.2(3) . . Y C24 C25 C26 118.1(3) . . Y C24 C25 C28 120.8(4) . . Y C26 C25 C28 120.9(4) . . Y C27 C26 C25 121.3(3) . . Y C26 C27 C22 119.3(3) . . Y _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.224 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.051