Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Andrew Burrows' _publ_contact_author_address ; Department of Chemistry University of Bath Claverton Down Bath BA2 7AY UNITED KINGDOM ; _publ_section_title ; Structural manipulation through control of hydrogen bonding faces: the effects of cation substitution on the guanidinium sulfonate structure ; _publ_contact_author_email A.D.BURROWS@BATH.AC.UK loop_ _publ_author_name A.D.Burrows N.J.Burke M.Mahon J.E.Warren # Attachment 'burke-gs.cif' data_compound_1a_bath112 _database_code_depnum_ccdc_archive 'CCDC 604278' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 N3 O3 S' _chemical_formula_weight 281.33 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 P21/n 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 8.884(3) _cell_length_b 40.601(11) _cell_length_c 10.980(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.180(4) _cell_angle_gamma 90.00 _cell_volume 3937.7(19) _cell_formula_units_Z 12 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5224 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 23.43 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.00 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.67780 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23498 _diffrn_reflns_av_R_equivalents 0.1434 _diffrn_reflns_av_sigmaI/netI 0.1632 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 22.07 _reflns_number_total 5579 _reflns_number_gt 4204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT V7.06a' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.1239P)^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 SHELXL _refine_ls_extinction_coef 0.049(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5579 _refine_ls_number_parameters 515 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1088 _refine_ls_R_factor_gt 0.0903 _refine_ls_wR_factor_ref 0.2245 _refine_ls_wR_factor_gt 0.2096 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.44094(12) 0.05768(3) 0.73437(10) 0.0316(4) Uani 1 1 d . . . S2 S 0.94757(12) 0.04632(3) 0.23134(10) 0.0301(4) Uani 1 1 d . . . S3 S 0.65384(12) 0.22910(3) 0.29322(10) 0.0308(4) Uani 1 1 d . . . O1 O 0.5583(3) 0.05371(7) 0.8348(3) 0.0332(8) Uani 1 1 d . . . O2 O 0.2987(3) 0.04320(7) 0.7617(3) 0.0348(8) Uani 1 1 d . . . O3 O 0.4875(4) 0.04609(8) 0.6190(3) 0.0415(8) Uani 1 1 d . . . O4 O 1.0526(3) 0.03219(7) 0.3272(3) 0.0341(8) Uani 1 1 d . . . O5 O 0.7920(3) 0.04311(7) 0.2574(3) 0.0331(8) Uani 1 1 d . . . O6 O 0.9722(3) 0.03392(7) 0.1114(3) 0.0357(8) Uani 1 1 d . . . O7 O 0.5389(3) 0.23219(7) 0.1902(3) 0.0351(8) Uani 1 1 d . . . O8 O 0.8018(3) 0.23949(7) 0.2624(3) 0.0336(8) Uani 1 1 d . . . O9 O 0.6116(4) 0.24594(7) 0.4003(3) 0.0343(8) Uani 1 1 d . . . N1 N 0.5146(4) 0.03415(9) 1.0873(3) 0.0343(9) Uani 1 1 d . . . H1A H 0.5368 0.0347 1.0111 0.041 Uiso 1 1 calc R . . H1B H 0.5859 0.0375 1.1480 0.041 Uiso 1 1 calc R . . N2 N 0.2664(4) 0.02302(9) 1.0203(3) 0.0350(9) Uani 1 1 d . . . H2B H 0.1730 0.0192 1.0362 0.042 Uiso 1 1 calc R . . H2A H 0.2881 0.0234 0.9440 0.042 Uiso 1 1 calc R . . N3 N 0.3405(4) 0.02756(9) 1.2251(3) 0.0333(9) Uani 1 1 d . . . H3 H 0.2474 0.0222 1.2377 0.040 Uiso 1 1 calc R . . N4 N 1.0239(4) 0.03997(9) 0.5835(3) 0.0323(9) Uani 1 1 d . . . H4B H 1.0976 0.0443 0.6414 0.039 Uiso 1 1 calc R . . H4A H 1.0445 0.0362 0.5081 0.039 Uiso 1 1 calc R . . N5 N 0.7709(4) 0.03380(10) 0.5221(3) 0.0374(10) Uani 1 1 d . . . H5B H 0.6763 0.0340 0.5391 0.045 Uiso 1 1 calc R . . H5A H 0.7913 0.0300 0.4468 0.045 Uiso 1 1 calc R . . N6 N 0.8494(4) 0.04474(9) 0.7224(3) 0.0323(9) Uani 1 1 d . . . H6 H 0.7536 0.0451 0.7359 0.039 Uiso 1 1 calc R . . N7 N 0.5802(4) 0.24174(9) -0.0685(4) 0.0368(9) Uani 1 1 d . . . H7A H 0.5597 0.2384 0.0072 0.044 Uiso 1 1 calc R . . H7B H 0.5079 0.2400 -0.1297 0.044 Uiso 1 1 calc R . . N8 N 0.8270(4) 0.25196(9) 0.0010(3) 0.0344(9) Uani 1 1 d . . . H8B H 0.9195 0.2572 -0.0135 0.041 Uiso 1 1 calc R . . H8A H 0.8066 0.2485 0.0766 0.041 Uiso 1 1 calc R . . N9 N 0.7511(4) 0.25462(9) -0.2033(4) 0.0367(10) Uani 1 1 d . . . H9 H 0.8424 0.2617 -0.2138 0.044 Uiso 1 1 calc R . . C1 C 0.4099(5) 0.10072(11) 0.7170(4) 0.0336(11) Uani 1 1 d . . . C2 C 0.4441(5) 0.11502(12) 0.6105(5) 0.0427(12) Uani 1 1 d . . . H2 H 0.4801 0.1017 0.5488 0.051 Uiso 1 1 calc R . . C3 C 0.4271(6) 0.14869(13) 0.5912(5) 0.0480(13) Uani 1 1 d . . . H3A H 0.4517 0.1582 0.5168 0.058 Uiso 1 1 calc R . . C4 C 0.3753(5) 0.16801(13) 0.6787(5) 0.0484(13) Uani 1 1 d . . . H4 H 0.3641 0.1910 0.6648 0.058 Uiso 1 1 calc R . . C5 C 0.3381(5) 0.15457(11) 0.7896(5) 0.0400(12) Uani 1 1 d . . . C6 C 0.2853(6) 0.17434(12) 0.8814(5) 0.0517(14) Uani 1 1 d . . . H6A H 0.2728 0.1973 0.8682 0.062 Uiso 1 1 calc R . . C7 C 0.2526(6) 0.16099(13) 0.9875(5) 0.0484(13) Uani 1 1 d . . . H7 H 0.2184 0.1747 1.0490 0.058 Uiso 1 1 calc R . . C8 C 0.2680(6) 0.12759(12) 1.0081(5) 0.0448(13) Uani 1 1 d . . . H8 H 0.2431 0.1186 1.0833 0.054 Uiso 1 1 calc R . . C9 C 0.3178(5) 0.10740(12) 0.9235(4) 0.0375(11) Uani 1 1 d . . . H9A H 0.3275 0.0845 0.9397 0.045 Uiso 1 1 calc R . . C10 C 0.3556(5) 0.12018(11) 0.8107(4) 0.0346(11) Uani 1 1 d . . . C11 C 0.9876(5) 0.08906(10) 0.2334(4) 0.0296(10) Uani 1 1 d . . . C12 C 1.0890(5) 0.10093(12) 0.3239(4) 0.0382(11) Uani 1 1 d . . . H12 H 1.1398 0.0860 0.3811 0.046 Uiso 1 1 calc R . . C13 C 1.1206(6) 0.13472(13) 0.3350(5) 0.0461(13) Uani 1 1 d . . . H13 H 1.1912 0.1427 0.3993 0.055 Uiso 1 1 calc R . . C14 C 1.0484(6) 0.15583(13) 0.2519(5) 0.0437(12) Uani 1 1 d . . . H14 H 1.0696 0.1787 0.2588 0.052 Uiso 1 1 calc R . . C15 C 0.9429(5) 0.14456(11) 0.1558(4) 0.0391(12) Uani 1 1 d . . . C16 C 0.8714(6) 0.16663(12) 0.0674(5) 0.0454(13) Uani 1 1 d . . . H16 H 0.8938 0.1895 0.0739 0.055 Uiso 1 1 calc R . . C17 C 0.7725(6) 0.15579(12) -0.0255(5) 0.0487(13) Uani 1 1 d . . . H17 H 0.7269 0.1708 -0.0847 0.058 Uiso 1 1 calc R . . C18 C 0.7370(5) 0.12198(12) -0.0341(5) 0.0430(12) Uani 1 1 d . . . H18 H 0.6663 0.1143 -0.0988 0.052 Uiso 1 1 calc R . . C19 C 0.8031(5) 0.10046(11) 0.0491(4) 0.0339(11) Uani 1 1 d . . . H19 H 0.7768 0.0778 0.0422 0.041 Uiso 1 1 calc R . . C20 C 0.9091(5) 0.11063(10) 0.1451(4) 0.0323(11) Uani 1 1 d . . . C21 C 0.6662(5) 0.18678(10) 0.3288(4) 0.0304(10) Uani 1 1 d . . . C22 C 0.5820(5) 0.16497(11) 0.2547(4) 0.0346(11) Uani 1 1 d . . . H22 H 0.5165 0.1730 0.1871 0.041 Uiso 1 1 calc R . . C23 C 0.5910(6) 0.13132(12) 0.2769(5) 0.0424(12) Uani 1 1 d . . . H23 H 0.5338 0.1165 0.2234 0.051 Uiso 1 1 calc R . . C24 C 0.6798(5) 0.11984(12) 0.3730(5) 0.0432(13) Uani 1 1 d . . . H24 H 0.6846 0.0967 0.3865 0.052 Uiso 1 1 calc R . . C25 C 0.7671(5) 0.14082(11) 0.4557(4) 0.0356(11) Uani 1 1 d . . . C26 C 0.8584(6) 0.12880(12) 0.5569(5) 0.0455(13) Uani 1 1 d . . . H26 H 0.8625 0.1057 0.5714 0.055 Uiso 1 1 calc R . . C27 C 0.9419(6) 0.14927(13) 0.6357(5) 0.0537(14) Uani 1 1 d . . . H27 H 1.0015 0.1407 0.7056 0.064 Uiso 1 1 calc R . . C28 C 0.9384(6) 0.18304(13) 0.6123(5) 0.0457(12) Uani 1 1 d . . . H28 H 0.9984 0.1974 0.6658 0.055 Uiso 1 1 calc R . . C29 C 0.8519(5) 0.19566(11) 0.5154(4) 0.0356(11) Uani 1 1 d . . . H29 H 0.8515 0.2188 0.5024 0.043 Uiso 1 1 calc R . . C30 C 0.7615(5) 0.17525(11) 0.4324(4) 0.0316(11) Uani 1 1 d . . . C31 C 0.3736(5) 0.02811(10) 1.1105(4) 0.0289(10) Uani 1 1 d . . . C32 C 0.4451(5) 0.03500(11) 1.3308(4) 0.0378(11) Uani 1 1 d . . . H32A H 0.3936 0.0328 1.4050 0.057 Uiso 1 1 calc R . . H32B H 0.4822 0.0576 1.3246 0.057 Uiso 1 1 calc R . . H32C H 0.5306 0.0197 1.3349 0.057 Uiso 1 1 calc R . . C33 C 0.8820(5) 0.03912(10) 0.6098(4) 0.0301(10) Uani 1 1 d . . . C34 C 0.9613(5) 0.05023(13) 0.8230(4) 0.0430(12) Uani 1 1 d . . . H34A H 0.9118 0.0540 0.8974 0.064 Uiso 1 1 calc R . . H34B H 1.0217 0.0696 0.8065 0.064 Uiso 1 1 calc R . . H34C H 1.0274 0.0309 0.8344 0.064 Uiso 1 1 calc R . . C35 C 0.7192(5) 0.24934(10) -0.0904(4) 0.0321(11) Uani 1 1 d . . . C36 C 0.6454(6) 0.24951(12) -0.3099(5) 0.0426(13) Uani 1 1 d . . . H36A H 0.6934 0.2551 -0.3834 0.064 Uiso 1 1 calc R . . H36B H 0.5565 0.2635 -0.3052 0.064 Uiso 1 1 calc R . . H36C H 0.6141 0.2264 -0.3139 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0312(7) 0.0360(7) 0.0300(7) -0.0009(5) 0.0151(5) 0.0008(5) S2 0.0325(7) 0.0314(7) 0.0291(7) 0.0005(5) 0.0157(5) -0.0003(5) S3 0.0333(7) 0.0311(7) 0.0310(7) 0.0012(5) 0.0167(5) 0.0003(5) O1 0.0337(17) 0.0363(18) 0.0318(17) 0.0010(13) 0.0133(14) 0.0018(13) O2 0.0311(17) 0.0362(18) 0.0394(18) -0.0017(14) 0.0149(14) -0.0027(13) O3 0.0467(19) 0.050(2) 0.0317(18) -0.0076(14) 0.0216(15) 0.0031(15) O4 0.0357(17) 0.0382(18) 0.0307(17) 0.0042(13) 0.0150(14) 0.0013(14) O5 0.0313(17) 0.0370(17) 0.0334(17) 0.0014(13) 0.0146(14) -0.0027(13) O6 0.0452(18) 0.0333(17) 0.0316(17) -0.0032(13) 0.0183(15) 0.0027(14) O7 0.0365(18) 0.0383(18) 0.0329(17) 0.0021(14) 0.0150(15) -0.0008(14) O8 0.0343(17) 0.0355(17) 0.0338(18) -0.0002(13) 0.0161(14) -0.0025(13) O9 0.0392(19) 0.0335(17) 0.0337(18) -0.0047(13) 0.0192(15) 0.0043(13) N1 0.031(2) 0.046(2) 0.028(2) -0.0002(17) 0.0152(17) -0.0043(17) N2 0.031(2) 0.049(2) 0.026(2) -0.0008(17) 0.0127(18) -0.0038(17) N3 0.031(2) 0.040(2) 0.032(2) 0.0014(17) 0.0177(17) 0.0003(16) N4 0.031(2) 0.041(2) 0.027(2) 0.0004(16) 0.0128(16) -0.0019(16) N5 0.033(2) 0.055(3) 0.027(2) 0.0031(18) 0.0129(18) -0.0013(18) N6 0.029(2) 0.040(2) 0.031(2) 0.0005(16) 0.0156(17) 0.0034(16) N7 0.028(2) 0.054(2) 0.031(2) 0.0023(17) 0.0133(18) 0.0002(17) N8 0.030(2) 0.046(2) 0.030(2) 0.0015(17) 0.0136(19) 0.0002(16) N9 0.029(2) 0.049(2) 0.035(2) 0.0012(17) 0.0175(18) -0.0006(17) C1 0.032(2) 0.037(3) 0.035(3) 0.002(2) 0.013(2) -0.0003(19) C2 0.042(3) 0.044(3) 0.044(3) 0.007(2) 0.016(2) -0.001(2) C3 0.042(3) 0.058(3) 0.046(3) 0.017(3) 0.016(3) -0.003(2) C4 0.041(3) 0.041(3) 0.065(4) 0.015(3) 0.013(3) -0.004(2) C5 0.032(2) 0.033(3) 0.056(3) 0.004(2) 0.011(2) -0.002(2) C6 0.051(3) 0.031(3) 0.076(4) 0.002(3) 0.019(3) 0.004(2) C7 0.048(3) 0.043(3) 0.058(3) -0.013(3) 0.023(3) 0.004(2) C8 0.049(3) 0.043(3) 0.047(3) -0.004(2) 0.024(2) 0.005(2) C9 0.037(3) 0.034(3) 0.044(3) 0.002(2) 0.016(2) 0.003(2) C10 0.029(2) 0.033(3) 0.042(3) 0.003(2) 0.009(2) -0.0024(19) C11 0.029(2) 0.032(2) 0.030(2) -0.0040(19) 0.0141(19) -0.0019(19) C12 0.041(3) 0.044(3) 0.032(3) -0.002(2) 0.014(2) 0.001(2) C13 0.049(3) 0.050(3) 0.042(3) -0.007(2) 0.014(2) -0.015(2) C14 0.050(3) 0.038(3) 0.046(3) -0.006(2) 0.017(3) -0.007(2) C15 0.045(3) 0.035(3) 0.040(3) -0.001(2) 0.018(2) 0.005(2) C16 0.052(3) 0.033(3) 0.053(3) 0.002(2) 0.017(3) 0.004(2) C17 0.056(3) 0.039(3) 0.052(3) 0.008(2) 0.010(3) 0.011(2) C18 0.039(3) 0.048(3) 0.043(3) 0.004(2) 0.011(2) 0.006(2) C19 0.039(3) 0.032(3) 0.033(3) -0.001(2) 0.015(2) -0.002(2) C20 0.032(2) 0.032(3) 0.037(3) -0.003(2) 0.021(2) 0.0010(19) C21 0.029(2) 0.031(2) 0.034(2) 0.0028(19) 0.019(2) -0.0018(19) C22 0.034(2) 0.037(3) 0.035(3) -0.002(2) 0.013(2) -0.003(2) C23 0.049(3) 0.039(3) 0.042(3) -0.007(2) 0.015(3) -0.009(2) C24 0.048(3) 0.032(3) 0.055(3) -0.001(2) 0.027(3) -0.004(2) C25 0.034(3) 0.032(3) 0.043(3) -0.001(2) 0.018(2) 0.002(2) C26 0.052(3) 0.032(3) 0.055(3) 0.015(2) 0.016(3) 0.005(2) C27 0.052(3) 0.050(3) 0.058(4) 0.018(3) -0.003(3) 0.005(3) C28 0.043(3) 0.045(3) 0.048(3) 0.006(2) 0.001(2) -0.002(2) C29 0.036(2) 0.033(3) 0.040(3) 0.001(2) 0.013(2) 0.000(2) C30 0.029(2) 0.031(3) 0.038(3) 0.000(2) 0.020(2) -0.0020(19) C31 0.033(2) 0.026(2) 0.030(3) 0.0005(18) 0.016(2) 0.0022(18) C32 0.043(3) 0.040(3) 0.032(3) -0.006(2) 0.011(2) -0.008(2) C33 0.033(3) 0.028(2) 0.032(3) 0.0061(19) 0.015(2) 0.0047(18) C34 0.042(3) 0.059(3) 0.031(3) -0.006(2) 0.018(2) 0.003(2) C35 0.035(3) 0.033(3) 0.031(3) 0.0004(19) 0.015(2) 0.0068(19) C36 0.035(3) 0.058(3) 0.036(3) -0.005(2) 0.009(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.442(3) . ? S1 O3 1.453(3) . ? S1 O2 1.454(3) . ? S1 C1 1.776(5) . ? S2 O4 1.447(3) . ? S2 O5 1.447(3) . ? S2 O6 1.448(3) . ? S2 C11 1.771(4) . ? S3 O9 1.445(3) . ? S3 O7 1.445(3) . ? S3 O8 1.455(3) . ? S3 C21 1.763(4) . ? N1 C31 1.328(5) . ? N2 C31 1.315(5) . ? N3 C31 1.323(5) . ? N3 C32 1.438(6) . ? N4 C33 1.323(5) . ? N5 C33 1.321(5) . ? N6 C33 1.320(5) . ? N6 C34 1.421(6) . ? N7 C35 1.320(6) . ? N8 C35 1.315(6) . ? N9 C35 1.318(6) . ? N9 C36 1.435(6) . ? C1 C2 1.368(6) . ? C1 C10 1.422(6) . ? C2 C3 1.389(7) . ? C3 C4 1.358(7) . ? C4 C5 1.406(7) . ? C5 C6 1.407(7) . ? C5 C10 1.421(6) . ? C6 C7 1.345(7) . ? C7 C8 1.379(7) . ? C8 C9 1.348(7) . ? C9 C10 1.417(6) . ? C11 C12 1.356(6) . ? C11 C20 1.431(6) . ? C12 C13 1.403(7) . ? C13 C14 1.361(7) . ? C14 C15 1.410(7) . ? C15 C20 1.412(6) . ? C15 C16 1.419(7) . ? C16 C17 1.347(7) . ? C17 C18 1.410(7) . ? C18 C19 1.352(6) . ? C19 C20 1.398(6) . ? C21 C22 1.370(6) . ? C21 C30 1.422(6) . ? C22 C23 1.389(7) . ? C23 C24 1.332(7) . ? C24 C25 1.414(7) . ? C25 C26 1.392(7) . ? C25 C30 1.421(6) . ? C26 C27 1.360(7) . ? C27 C28 1.395(7) . ? C28 C29 1.344(6) . ? C29 C30 1.416(6) . ? 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 O3 112.33(18) . . ? O1 S1 O2 111.68(18) . . ? O3 S1 O2 112.61(19) . . ? O1 S1 C1 106.45(19) . . ? O3 S1 C1 106.3(2) . . ? O2 S1 C1 106.97(19) . . ? O4 S2 O5 112.05(17) . . ? O4 S2 O6 112.00(18) . . ? O5 S2 O6 112.91(18) . . ? O4 S2 C11 105.44(19) . . ? O5 S2 C11 106.28(18) . . ? O6 S2 C11 107.61(19) . . ? O9 S3 O7 111.88(18) . . ? O9 S3 O8 111.88(19) . . ? O7 S3 O8 111.89(18) . . ? O9 S3 C21 107.22(19) . . ? O7 S3 C21 106.26(19) . . ? O8 S3 C21 107.33(18) . . ? C31 N3 C32 125.0(4) . . ? C33 N6 C34 123.3(4) . . ? C35 N9 C36 123.7(4) . . ? C2 C1 C10 120.4(4) . . ? C2 C1 S1 117.6(4) . . ? C10 C1 S1 122.0(3) . . ? C1 C2 C3 121.2(5) . . ? C4 C3 C2 120.0(5) . . ? C3 C4 C5 121.2(5) . . ? C4 C5 C6 121.8(5) . . ? C4 C5 C10 119.3(4) . . ? C6 C5 C10 118.9(4) . . ? C7 C6 C5 120.7(5) . . ? C6 C7 C8 120.7(5) . . ? C9 C8 C7 121.3(5) . . ? C8 C9 C10 120.4(5) . . ? C9 C10 C5 118.0(4) . . ? C9 C10 C1 124.1(4) . . ? C5 C10 C1 117.9(4) . . ? C12 C11 C20 121.1(4) . . ? C12 C11 S2 118.3(4) . . ? C20 C11 S2 120.6(3) . . ? C11 C12 C13 121.4(5) . . ? C14 C13 C12 118.8(5) . . ? C13 C14 C15 121.7(5) . . ? C14 C15 C20 119.8(4) . . ? C14 C15 C16 121.3(5) . . ? C20 C15 C16 118.9(5) . . ? C17 C16 C15 121.3(5) . . ? C16 C17 C18 119.4(5) . . ? C19 C18 C17 120.5(5) . . ? C18 C19 C20 121.8(4) . . ? C19 C20 C15 118.1(4) . . ? C19 C20 C11 124.7(4) . . ? C15 C20 C11 117.2(4) . . ? C22 C21 C30 120.2(4) . . ? C22 C21 S3 118.7(3) . . ? C30 C21 S3 121.1(3) . . ? C21 C22 C23 120.9(4) . . ? C24 C23 C22 120.1(5) . . ? C23 C24 C25 122.3(5) . . ? C26 C25 C24 122.3(4) . . ? C26 C25 C30 119.6(4) . . ? C24 C25 C30 118.1(4) . . ? C27 C26 C25 121.7(4) . . ? C26 C27 C28 118.9(5) . . ? C29 C28 C27 121.3(5) . . ? C28 C29 C30 121.5(4) . . ? C29 C30 C25 117.0(4) . . ? C29 C30 C21 124.7(4) . . ? C25 C30 C21 118.3(4) . . ? N2 C31 N3 119.8(4) . . ? N2 C31 N1 120.4(4) . . ? N3 C31 N1 119.8(4) . . ? N6 C33 N5 119.3(4) . . ? N6 C33 N4 120.7(4) . . ? N5 C33 N4 120.0(4) . . ? N8 C35 N9 119.4(4) . . ? N8 C35 N7 119.9(4) . . ? N9 C35 N7 120.6(4) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 22.07 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.564 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.119 #===END data_compound_1b_k02njb5 _database_code_depnum_ccdc_archive 'CCDC 604279' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H19 N3 O4 S' _chemical_formula_weight 313.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3850(2) _cell_length_b 15.9310(5) _cell_length_c 25.3940(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2987.61(18) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13638 _diffrn_reflns_av_R_equivalents 0.0937 _diffrn_reflns_av_sigmaI/netI 0.1040 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3358 _reflns_number_gt 1958 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0518P)^2^+0.3952P] 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 3358 _refine_ls_number_parameters 199 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1248 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.93957(8) -0.09769(4) 0.11163(3) 0.0219(2) Uani 1 1 d . . . O1 O 1.1035(2) -0.05499(11) 0.09341(8) 0.0264(5) Uani 1 1 d . . . O2 O 0.9505(2) -0.18860(10) 0.10563(8) 0.0273(5) Uani 1 1 d . . . O3 O 0.7773(2) -0.06349(11) 0.08633(8) 0.0268(5) Uani 1 1 d . . . O4 O 1.1728(3) -0.07236(13) -0.01567(9) 0.0306(5) Uani 1 1 d D . . N1 N 1.4415(3) -0.15303(14) 0.09084(10) 0.0297(6) Uani 1 1 d . . . H1A H 1.3387 -0.1285 0.0993 0.036 Uiso 1 1 calc R . . H1B H 1.5442 -0.1254 0.0939 0.036 Uiso 1 1 calc R . . N2 N 1.2863(3) -0.27289(13) 0.06896(10) 0.0267(6) Uani 1 1 d . . . H2A H 1.1855 -0.2452 0.0751 0.032 Uiso 1 1 calc R . . N3 N 1.5979(3) -0.26794(13) 0.06087(9) 0.0260(5) Uani 1 1 d . . . H3A H 1.5992 -0.3200 0.0493 0.031 Uiso 1 1 calc R . . H3B H 1.6999 -0.2399 0.0641 0.031 Uiso 1 1 calc R . . C1 C 1.4416(3) -0.23165(16) 0.07349(10) 0.0217(6) Uani 1 1 d . . . C2 C 1.2721(3) -0.36106(17) 0.05442(14) 0.0322(7) Uani 1 1 d . . . H2C H 1.3496 -0.3952 0.0779 0.039 Uiso 1 1 calc R . . H2B H 1.3151 -0.3688 0.0178 0.039 Uiso 1 1 calc R . . C3 C 1.0774(4) -0.39019(19) 0.05882(14) 0.0396(8) Uani 1 1 d . . . H3C H 1.0364 -0.3843 0.0953 0.059 Uiso 1 1 calc R . . H3D H 1.0690 -0.4492 0.0482 0.059 Uiso 1 1 calc R . . H3E H 1.0007 -0.3559 0.0358 0.059 Uiso 1 1 calc R . . C4 C 0.9230(3) -0.07716(15) 0.18009(11) 0.0207(6) Uani 1 1 d . . . C5 C 0.9636(3) -0.14104(16) 0.21415(12) 0.0246(6) Uani 1 1 d . . . H5 H 0.9939 -0.1947 0.2005 0.030 Uiso 1 1 calc R . . C6 C 0.9612(4) -0.12877(17) 0.26860(12) 0.0295(7) Uani 1 1 d . . . H6 H 0.9930 -0.1735 0.2916 0.035 Uiso 1 1 calc R . . C7 C 0.9132(3) -0.05262(17) 0.28877(12) 0.0282(7) Uani 1 1 d . . . H7 H 0.9097 -0.0449 0.3258 0.034 Uiso 1 1 calc R . . C8 C 0.8684(3) 0.01519(16) 0.25500(11) 0.0246(6) Uani 1 1 d . . . C9 C 0.8163(3) 0.09404(17) 0.27631(12) 0.0278(7) Uani 1 1 d . . . H9 H 0.8091 0.1009 0.3134 0.033 Uiso 1 1 calc R . . C10 C 0.7767(4) 0.15967(17) 0.24429(13) 0.0299(7) Uani 1 1 d . . . H10 H 0.7415 0.2120 0.2591 0.036 Uiso 1 1 calc R . . C11 C 0.7876(3) 0.15059(17) 0.18920(13) 0.0295(7) Uani 1 1 d . . . H11 H 0.7618 0.1972 0.1671 0.035 Uiso 1 1 calc R . . C12 C 0.8350(3) 0.07539(16) 0.16723(12) 0.0257(6) Uani 1 1 d . . . H12 H 0.8409 0.0702 0.1300 0.031 Uiso 1 1 calc R . . C13 C 0.8756(3) 0.00481(16) 0.19948(11) 0.0216(6) Uani 1 1 d . . . H4A H 1.151(4) -0.059(2) 0.0178(4) 0.064(12) Uiso 1 1 d D . . H4B H 1.179(5) -0.0252(15) -0.0344(14) 0.083(14) Uiso 1 1 d 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 0.0218(3) 0.0219(4) 0.0219(4) -0.0022(3) 0.0023(3) -0.0013(3) O1 0.0247(9) 0.0279(11) 0.0266(11) -0.0012(9) 0.0059(8) -0.0033(8) O2 0.0313(10) 0.0185(10) 0.0320(12) -0.0063(8) 0.0047(9) -0.0006(8) O3 0.0245(9) 0.0293(11) 0.0267(12) 0.0003(9) -0.0024(8) -0.0007(8) O4 0.0361(11) 0.0300(12) 0.0256(13) -0.0041(10) 0.0022(9) -0.0008(9) N1 0.0214(11) 0.0288(14) 0.0388(15) -0.0104(11) 0.0009(11) -0.0003(10) N2 0.0211(11) 0.0234(13) 0.0357(16) -0.0053(11) 0.0003(10) 0.0012(9) N3 0.0232(11) 0.0225(13) 0.0321(15) -0.0037(11) 0.0020(10) -0.0010(9) C1 0.0230(13) 0.0238(16) 0.0182(14) 0.0000(12) -0.0011(11) -0.0005(12) C2 0.0291(14) 0.0236(16) 0.044(2) -0.0059(14) -0.0007(13) -0.0006(12) C3 0.0307(15) 0.0335(18) 0.055(2) -0.0067(16) -0.0031(15) -0.0050(13) C4 0.0181(12) 0.0209(14) 0.0233(15) 0.0018(12) 0.0016(11) -0.0027(11) C5 0.0245(13) 0.0212(15) 0.0281(16) 0.0022(13) 0.0018(12) 0.0002(11) C6 0.0305(15) 0.0272(16) 0.0310(17) 0.0095(13) -0.0041(12) -0.0002(12) C7 0.0306(14) 0.0343(18) 0.0198(15) 0.0056(13) -0.0018(12) -0.0027(13) C8 0.0218(13) 0.0265(16) 0.0254(17) 0.0000(13) 0.0006(11) -0.0011(11) C9 0.0283(14) 0.0336(17) 0.0217(16) -0.0049(14) 0.0001(12) -0.0008(12) C10 0.0309(15) 0.0245(16) 0.0344(19) -0.0061(14) 0.0006(13) 0.0021(12) C11 0.0351(15) 0.0219(16) 0.0314(18) 0.0004(14) 0.0020(13) 0.0028(12) C12 0.0275(14) 0.0269(16) 0.0228(16) 0.0013(13) 0.0019(12) 0.0009(12) C13 0.0177(12) 0.0240(15) 0.0231(16) 0.0005(13) -0.0005(10) -0.0018(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 O2 1.4585(18) . ? S1 O1 1.4637(18) . ? S1 O3 1.4647(18) . ? S1 C4 1.773(3) . ? N1 C1 1.328(3) . ? N2 C1 1.327(3) . ? N2 C2 1.456(3) . ? N3 C1 1.330(3) . ? C2 C3 1.515(4) . ? C4 C5 1.369(4) . ? C4 C13 1.439(3) . ? C5 C6 1.397(4) . ? C6 C7 1.364(4) . ? C7 C8 1.418(4) . ? C8 C13 1.421(4) . ? C8 C9 1.421(4) . ? C9 C10 1.356(4) . ? C10 C11 1.409(4) . ? C11 C12 1.367(4) . ? C12 C13 1.423(4) . ? 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 112.49(10) . . ? O2 S1 O3 111.66(10) . . ? O1 S1 O3 111.41(11) . . ? O2 S1 C4 106.82(11) . . ? O1 S1 C4 106.33(11) . . ? O3 S1 C4 107.77(11) . . ? C1 N2 C2 124.2(2) . . ? N2 C1 N1 119.7(2) . . ? N2 C1 N3 120.9(2) . . ? N1 C1 N3 119.4(2) . . ? N2 C2 C3 110.2(2) . . ? C5 C4 C13 120.8(3) . . ? C5 C4 S1 117.9(2) . . ? C13 C4 S1 121.31(19) . . ? C4 C5 C6 121.2(3) . . ? C7 C6 C5 120.0(3) . . ? C6 C7 C8 120.7(3) . . ? C7 C8 C13 120.2(2) . . ? C7 C8 C9 120.4(3) . . ? C13 C8 C9 119.4(2) . . ? C10 C9 C8 120.8(3) . . ? C9 C10 C11 120.3(3) . . ? C12 C11 C10 120.7(3) . . ? C11 C12 C13 120.8(3) . . ? C8 C13 C12 118.1(2) . . ? C8 C13 C4 117.0(2) . . ? C12 C13 C4 124.9(3) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.445 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.074 #===END data_compound_1c_h02njb2 _database_code_depnum_ccdc_archive 'CCDC 604280' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H19 N3 O4 S' _chemical_formula_weight 313.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.0940(2) _cell_length_b 10.6850(2) _cell_length_c 12.7100(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.954(1) _cell_angle_gamma 90.00 _cell_volume 1468.29(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10014 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type Multiscan _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29129 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3358 _reflns_number_gt 2597 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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 [1.00000+0.00000exp(0.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.6067*P+(0.0453P)^2^+0.0000sin\q/\l] where P = 0.00000Fo^2^ + 1.00000Fc^2^ ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0167(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3358 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0885 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.20452(4) -0.04447(4) 0.23029(3) 0.02409(14) Uani 1 1 d . . . O1 O 0.30632(12) -0.13207(12) 0.23538(10) 0.0389(3) Uani 1 1 d . . . O2 O 0.22024(11) 0.06864(11) 0.17026(9) 0.0283(3) Uani 1 1 d . . . O3 O 0.08508(12) -0.10357(11) 0.18909(9) 0.0321(3) Uani 1 1 d . . . O4 O -0.00464(12) 0.16463(12) 0.03641(11) 0.0304(3) Uani 1 1 d . . . N1 N 0.03490(14) 0.62188(13) 0.17736(12) 0.0325(4) Uani 1 1 d . . . H1B H 0.0851 0.6865 0.1834 0.039 Uiso 1 1 calc R . . H1A H -0.0374 0.6296 0.1943 0.039 Uiso 1 1 calc R . . N2 N -0.01029(14) 0.41659(14) 0.13539(13) 0.0277(3) Uani 1 1 d . . . N3 N 0.17669(13) 0.49745(13) 0.11638(11) 0.0283(3) Uani 1 1 d . . . C1 C 0.06831(16) 0.51246(15) 0.14264(12) 0.0248(4) Uani 1 1 d . . . C2 C 0.25773(18) 0.60259(18) 0.10848(16) 0.0387(5) Uani 1 1 d . . . H2D H 0.2480 0.6263 0.0325 0.058 Uiso 1 1 calc R . . H2E H 0.3438 0.5785 0.1384 0.058 Uiso 1 1 calc R . . H2C H 0.2359 0.6738 0.1492 0.058 Uiso 1 1 calc R . . C3 C 0.21191(16) 0.37588(17) 0.08003(16) 0.0344(4) Uani 1 1 d . . . H3A H 0.1987 0.3108 0.1306 0.052 Uiso 1 1 calc R . . H3B H 0.2994 0.3776 0.0771 0.052 Uiso 1 1 calc R . . H3C H 0.1612 0.3577 0.0080 0.052 Uiso 1 1 calc R . . C4 C 0.20961(15) 0.00049(14) 0.36568(12) 0.0228(3) Uani 1 1 d . . . C5 C 0.30522(16) -0.04534(15) 0.44399(14) 0.0281(4) Uani 1 1 d . . . H5 H 0.3665 -0.0965 0.4240 0.034 Uiso 1 1 calc R . . C6 C 0.31354(17) -0.01745(17) 0.55369(14) 0.0338(4) Uani 1 1 d . . . H6 H 0.3809 -0.0484 0.6072 0.041 Uiso 1 1 calc R . . C7 C 0.22534(17) 0.05354(16) 0.58276(14) 0.0318(4) Uani 1 1 d . . . H7 H 0.2308 0.0706 0.6571 0.038 Uiso 1 1 calc R . . C8 C 0.12497(16) 0.10303(14) 0.50478(13) 0.0250(4) Uani 1 1 d . . . C9 C 0.03160(17) 0.17546(15) 0.53578(14) 0.0305(4) Uani 1 1 d . . . H9 H 0.0358 0.1900 0.6102 0.037 Uiso 1 1 calc R . . C10 C -0.06366(17) 0.22439(16) 0.46094(15) 0.0329(4) Uani 1 1 d . . . H10 H -0.1256 0.2725 0.4831 0.039 Uiso 1 1 calc R . . C11 C -0.07025(16) 0.20355(16) 0.35045(15) 0.0311(4) Uani 1 1 d . . . H11 H -0.1358 0.2399 0.2983 0.037 Uiso 1 1 calc R . . C12 C 0.01615(15) 0.13186(15) 0.31706(13) 0.0263(4) Uani 1 1 d . . . H12 H 0.0091 0.1176 0.2421 0.032 Uiso 1 1 calc R . . C13 C 0.11641(14) 0.07847(14) 0.39329(12) 0.0218(3) Uani 1 1 d . . . H1 H -0.021(2) 0.144(2) -0.028(2) 0.061(8) Uiso 1 1 d . . . H3 H 0.056(3) 0.123(2) 0.066(2) 0.067(8) Uiso 1 1 d . . . H2A H -0.080(2) 0.4278(19) 0.1527(16) 0.037(6) Uiso 1 1 d . . . H2B H 0.0040(19) 0.348(2) 0.1077(16) 0.036(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0268(2) 0.0220(2) 0.0246(2) -0.00206(15) 0.00812(16) 0.00022(15) O1 0.0442(8) 0.0365(7) 0.0384(7) -0.0013(6) 0.0140(6) 0.0165(6) O2 0.0310(6) 0.0282(6) 0.0268(6) 0.0027(5) 0.0092(5) -0.0033(5) O3 0.0366(7) 0.0315(6) 0.0287(6) -0.0075(5) 0.0081(5) -0.0118(5) O4 0.0298(7) 0.0336(7) 0.0278(7) -0.0023(5) 0.0062(5) 0.0024(5) N1 0.0372(9) 0.0249(7) 0.0359(8) -0.0024(6) 0.0096(7) -0.0019(6) N2 0.0245(8) 0.0236(7) 0.0370(8) -0.0020(6) 0.0109(6) -0.0012(6) N3 0.0272(8) 0.0281(7) 0.0301(7) -0.0011(6) 0.0073(6) -0.0048(6) C1 0.0283(9) 0.0251(8) 0.0198(8) 0.0039(6) 0.0024(6) 0.0001(7) C2 0.0382(11) 0.0392(11) 0.0410(11) -0.0011(8) 0.0135(9) -0.0161(8) C3 0.0245(9) 0.0353(10) 0.0442(11) -0.0048(8) 0.0093(8) 0.0015(7) C4 0.0246(8) 0.0196(7) 0.0243(8) 0.0003(6) 0.0059(6) -0.0031(6) C5 0.0272(9) 0.0254(8) 0.0312(9) 0.0026(7) 0.0050(7) 0.0011(7) C6 0.0328(10) 0.0372(10) 0.0270(9) 0.0053(7) -0.0027(7) -0.0019(8) C7 0.0387(10) 0.0333(9) 0.0222(8) -0.0010(7) 0.0046(7) -0.0094(8) C8 0.0291(9) 0.0214(8) 0.0255(8) -0.0016(6) 0.0083(7) -0.0082(6) C9 0.0397(10) 0.0243(8) 0.0317(9) -0.0079(7) 0.0170(8) -0.0087(7) C10 0.0343(10) 0.0232(8) 0.0460(11) -0.0046(8) 0.0194(8) -0.0010(7) C11 0.0282(9) 0.0274(9) 0.0385(10) 0.0036(7) 0.0094(8) 0.0035(7) C12 0.0276(9) 0.0252(8) 0.0267(8) 0.0020(7) 0.0074(7) 0.0008(7) C13 0.0242(8) 0.0180(7) 0.0238(8) -0.0002(6) 0.0067(6) -0.0039(6) _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 O3 1.4553(12) . ? S1 O1 1.4570(12) . ? S1 O2 1.4604(12) . ? S1 C4 1.7752(16) . ? N1 C1 1.331(2) . ? N2 C1 1.335(2) . ? N3 C1 1.328(2) . ? N3 C2 1.456(2) . ? N3 C3 1.461(2) . ? C4 C5 1.372(2) . ? C4 C13 1.431(2) . ? C5 C6 1.408(2) . ? C6 C7 1.353(3) . ? C7 C8 1.417(2) . ? C8 C9 1.418(2) . ? C8 C13 1.423(2) . ? C9 C10 1.358(3) . ? C10 C11 1.408(3) . ? C11 C12 1.367(2) . ? C12 C13 1.421(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O1 111.80(8) . . ? O3 S1 O2 112.14(7) . . ? O1 S1 O2 111.88(7) . . ? O3 S1 C4 107.14(7) . . ? O1 S1 C4 105.96(8) . . ? O2 S1 C4 107.51(7) . . ? C1 N3 C2 122.13(15) . . ? C1 N3 C3 120.56(14) . . ? C2 N3 C3 116.82(14) . . ? N3 C1 N1 121.64(15) . . ? N3 C1 N2 120.28(15) . . ? N1 C1 N2 118.09(16) . . ? C5 C4 C13 120.89(15) . . ? C5 C4 S1 117.26(13) . . ? C13 C4 S1 121.83(12) . . ? C4 C5 C6 120.74(16) . . ? C7 C6 C5 119.87(16) . . ? C6 C7 C8 121.41(16) . . ? C7 C8 C9 121.19(15) . . ? C7 C8 C13 119.62(15) . . ? C9 C8 C13 119.18(15) . . ? C10 C9 C8 121.19(16) . . ? C9 C10 C11 119.74(16) . . ? C12 C11 C10 121.02(16) . . ? C11 C12 C13 120.64(16) . . ? C12 C13 C8 118.18(15) . . ? C12 C13 C4 124.38(14) . . ? C8 C13 C4 117.44(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.283 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.094 #===END data_compound_2a_k03njb2 _database_code_depnum_ccdc_archive 'CCDC 604281' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 N3 O3 S' _chemical_formula_weight 281.33 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7420(2) _cell_length_b 28.3960(5) _cell_length_c 10.8770(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.953(1) _cell_angle_gamma 90.00 _cell_volume 2696.50(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.936 _exptl_absorpt_correction_T_max 1.089 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31192 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 27.45 _reflns_number_total 6046 _reflns_number_gt 4174 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0436P)^2^+1.8498P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0043(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6046 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.70744(6) 0.08632(2) 0.99879(5) 0.02310(16) Uani 1 1 d . . . S2 S 0.21310(6) 0.08385(2) 0.52793(5) 0.02275(16) Uani 1 1 d . . . O1 O 0.7561(2) 0.05590(6) 0.90122(15) 0.0330(4) Uani 1 1 d . . . O2 O 0.82160(18) 0.09029(6) 1.10024(14) 0.0279(4) Uani 1 1 d . . . O3 O 0.55785(18) 0.07312(6) 1.04028(14) 0.0313(4) Uani 1 1 d . . . O4 O 0.26008(19) 0.08747(6) 0.40311(14) 0.0313(4) Uani 1 1 d . . . O5 O 0.33244(17) 0.06396(6) 0.61170(14) 0.0264(4) Uani 1 1 d . . . O6 O 0.06839(18) 0.05921(6) 0.53886(15) 0.0298(4) Uani 1 1 d . . . N1 N 1.0495(2) 0.03434(8) 0.80830(17) 0.0311(5) Uani 1 1 d . . . H1B H 1.0761 0.0286 0.7328 0.037 Uiso 1 1 calc R . . H1A H 0.9520 0.0350 0.8248 0.037 Uiso 1 1 calc R . . N2 N 1.1142(2) 0.04983(7) 1.01116(17) 0.0254(4) Uani 1 1 d . . . H2A H 1.0154 0.0512 1.0227 0.031 Uiso 1 1 calc R . . N3 N 1.3033(2) 0.04094(7) 0.87312(18) 0.0294(5) Uani 1 1 d . . . H3A H 1.3743 0.0455 0.9322 0.035 Uiso 1 1 calc R . . H3B H 1.3297 0.0357 0.7974 0.035 Uiso 1 1 calc R . . N4 N 0.5440(2) 0.05837(8) 0.30297(17) 0.0305(5) Uani 1 1 d . . . H4A H 0.4481 0.0576 0.3239 0.037 Uiso 1 1 calc R . . H4B H 0.5650 0.0616 0.2252 0.037 Uiso 1 1 calc R . . N5 N 0.6222(2) 0.04994(7) 0.50518(16) 0.0256(5) Uani 1 1 d . . . H5A H 0.5245 0.0496 0.5212 0.031 Uiso 1 1 calc R . . N6 N 0.8013(2) 0.05562(7) 0.35735(17) 0.0258(5) Uani 1 1 d . . . H6A H 0.8762 0.0530 0.4142 0.031 Uiso 1 1 calc R . . H6B H 0.8223 0.0588 0.2795 0.031 Uiso 1 1 calc R . . C1 C 1.1572(3) 0.04199(8) 0.8981(2) 0.0238(5) Uani 1 1 d . . . C2 C 1.2195(3) 0.05630(9) 1.1174(2) 0.0264(5) Uani 1 1 d . . . H2D H 1.2877 0.0290 1.1260 0.040 Uiso 1 1 calc R . . H2B H 1.1614 0.0595 1.1916 0.040 Uiso 1 1 calc R . . H2C H 1.2805 0.0848 1.1063 0.040 Uiso 1 1 calc R . . C3 C 0.6827(3) 0.14277(8) 0.9319(2) 0.0235(5) Uani 1 1 d . . . C4 C 0.7464(3) 0.18183(9) 0.9862(2) 0.0287(6) Uani 1 1 d . . . H4 H 0.8088 0.1789 1.0600 0.034 Uiso 1 1 calc R . . C5 C 0.7194(3) 0.22697(9) 0.9325(2) 0.0328(6) Uani 1 1 d . . . C6 C 0.7800(4) 0.26861(10) 0.9881(3) 0.0497(8) Uani 1 1 d . . . H6 H 0.8406 0.2667 1.0630 0.060 Uiso 1 1 calc R . . C7 C 0.7520(4) 0.31136(11) 0.9347(3) 0.0624(10) Uani 1 1 d . . . H7 H 0.7933 0.3390 0.9727 0.075 Uiso 1 1 calc R . . C8 C 0.6634(4) 0.31493(11) 0.8251(3) 0.0610(9) Uani 1 1 d . . . H8 H 0.6451 0.3450 0.7888 0.073 Uiso 1 1 calc R . . C9 C 0.6028(4) 0.27576(10) 0.7695(3) 0.0495(8) Uani 1 1 d . . . H9 H 0.5424 0.2787 0.6948 0.059 Uiso 1 1 calc R . . C10 C 0.6292(3) 0.23055(9) 0.8222(2) 0.0343(6) Uani 1 1 d . . . C11 C 0.5664(3) 0.18916(10) 0.7676(2) 0.0397(7) Uani 1 1 d . . . H11 H 0.5060 0.1913 0.6927 0.048 Uiso 1 1 calc R . . C12 C 0.5913(3) 0.14613(9) 0.8210(2) 0.0331(6) Uani 1 1 d . . . H12 H 0.5475 0.1186 0.7839 0.040 Uiso 1 1 calc R . . C13 C 0.6570(3) 0.05472(8) 0.3889(2) 0.0224(5) Uani 1 1 d . . . C14 C 0.7333(3) 0.04524(9) 0.6080(2) 0.0299(6) Uani 1 1 d . . . H14A H 0.8037 0.0194 0.5919 0.045 Uiso 1 1 calc R . . H14B H 0.6800 0.0385 0.6832 0.045 Uiso 1 1 calc R . . H14C H 0.7913 0.0746 0.6185 0.045 Uiso 1 1 calc R . . C15 C 0.1818(3) 0.14203(9) 0.5806(2) 0.0270(5) Uani 1 1 d . . . C16 C 0.0964(3) 0.14835(10) 0.6867(2) 0.0359(6) Uani 1 1 d . . . H16 H 0.0547 0.1218 0.7261 0.043 Uiso 1 1 calc R . . C17 C 0.0738(3) 0.19237(10) 0.7328(2) 0.0399(7) Uani 1 1 d . . . H17 H 0.0178 0.1963 0.8047 0.048 Uiso 1 1 calc R . . C18 C 0.1334(3) 0.23191(10) 0.6738(2) 0.0366(6) Uani 1 1 d . . . C19 C 0.1078(4) 0.27882(11) 0.7191(3) 0.0497(8) Uani 1 1 d . . . H19 H 0.0508 0.2834 0.7901 0.060 Uiso 1 1 calc R . . C20 C 0.1656(4) 0.31625(11) 0.6599(3) 0.0591(9) Uani 1 1 d . . . H20 H 0.1484 0.3471 0.6901 0.071 Uiso 1 1 calc R . . C21 C 0.2505(4) 0.31033(11) 0.5546(3) 0.0577(9) Uani 1 1 d . . . H21 H 0.2907 0.3371 0.5151 0.069 Uiso 1 1 calc R . . C22 C 0.2757(4) 0.26619(11) 0.5085(3) 0.0478(8) Uani 1 1 d . . . H22 H 0.3319 0.2624 0.4367 0.057 Uiso 1 1 calc R . . C23 C 0.2177(3) 0.22658(9) 0.5686(2) 0.0338(6) Uani 1 1 d . . . C24 C 0.2408(3) 0.17955(9) 0.5219(2) 0.0316(6) Uani 1 1 d . . . H24 H 0.2970 0.1749 0.4505 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0233(3) 0.0274(3) 0.0186(3) 0.0017(2) 0.0010(2) 0.0013(2) S2 0.0218(3) 0.0282(3) 0.0183(3) -0.0019(2) 0.0004(2) 0.0007(2) O1 0.0438(11) 0.0303(10) 0.0252(9) -0.0005(8) 0.0058(8) 0.0076(8) O2 0.0264(9) 0.0345(10) 0.0223(8) 0.0054(7) -0.0023(7) 0.0015(7) O3 0.0248(9) 0.0432(11) 0.0258(9) 0.0059(8) 0.0003(7) -0.0046(8) O4 0.0346(10) 0.0391(11) 0.0204(8) -0.0006(8) 0.0033(7) 0.0041(8) O5 0.0237(9) 0.0340(10) 0.0214(8) 0.0012(7) 0.0010(7) 0.0049(7) O6 0.0220(9) 0.0367(10) 0.0305(9) -0.0036(8) 0.0005(7) -0.0046(7) N1 0.0278(12) 0.0456(14) 0.0199(11) 0.0008(9) 0.0000(9) -0.0046(9) N2 0.0199(10) 0.0344(12) 0.0220(10) 0.0020(9) 0.0021(8) 0.0003(8) N3 0.0244(11) 0.0442(13) 0.0195(10) -0.0035(9) 0.0013(8) -0.0027(9) N4 0.0222(11) 0.0519(15) 0.0174(10) 0.0014(9) -0.0004(8) 0.0001(10) N5 0.0196(10) 0.0394(12) 0.0179(10) 0.0001(9) 0.0016(8) 0.0000(9) N6 0.0225(11) 0.0383(12) 0.0165(10) 0.0015(9) -0.0001(8) 0.0010(9) C1 0.0250(13) 0.0258(13) 0.0205(12) 0.0032(9) 0.0009(10) -0.0007(10) C2 0.0291(13) 0.0297(13) 0.0203(12) -0.0017(10) -0.0001(10) -0.0017(10) C3 0.0219(12) 0.0284(13) 0.0204(11) 0.0019(10) 0.0030(9) 0.0015(10) C4 0.0302(14) 0.0314(14) 0.0240(12) 0.0012(10) -0.0016(10) -0.0015(10) C5 0.0367(15) 0.0303(15) 0.0316(14) -0.0004(11) 0.0044(11) -0.0001(11) C6 0.068(2) 0.0351(17) 0.0456(18) -0.0012(14) -0.0034(16) -0.0089(15) C7 0.094(3) 0.0326(18) 0.061(2) -0.0033(16) 0.006(2) -0.0106(17) C8 0.098(3) 0.0288(17) 0.057(2) 0.0077(15) 0.009(2) 0.0064(17) C9 0.069(2) 0.0362(17) 0.0424(17) 0.0107(14) -0.0008(15) 0.0073(15) C10 0.0422(16) 0.0294(15) 0.0315(14) 0.0052(11) 0.0038(12) 0.0057(12) C11 0.0487(17) 0.0401(17) 0.0289(14) 0.0018(12) -0.0107(12) 0.0068(13) C12 0.0400(15) 0.0315(14) 0.0270(13) -0.0011(11) -0.0074(11) 0.0033(11) C13 0.0236(13) 0.0227(12) 0.0208(12) -0.0022(9) 0.0009(9) 0.0012(9) C14 0.0256(13) 0.0442(16) 0.0195(12) 0.0019(11) -0.0010(10) 0.0005(11) C15 0.0259(13) 0.0313(14) 0.0231(12) 0.0003(10) -0.0052(10) 0.0019(10) C16 0.0413(16) 0.0337(15) 0.0331(14) -0.0024(12) 0.0065(12) 0.0042(12) C17 0.0485(17) 0.0406(17) 0.0314(15) -0.0026(12) 0.0095(13) 0.0042(13) C18 0.0414(16) 0.0385(16) 0.0295(14) 0.0018(12) -0.0027(12) 0.0025(12) C19 0.069(2) 0.0367(17) 0.0434(17) -0.0078(14) -0.0004(15) 0.0046(15) C20 0.093(3) 0.0298(17) 0.054(2) -0.0028(15) -0.0028(19) 0.0009(16) C21 0.083(3) 0.0356(18) 0.055(2) -0.0013(15) 0.0048(18) -0.0087(17) C22 0.062(2) 0.0415(18) 0.0401(17) 0.0028(14) 0.0073(14) -0.0084(15) C23 0.0365(15) 0.0362(16) 0.0280(14) 0.0045(11) -0.0038(11) -0.0013(12) C24 0.0322(14) 0.0366(15) 0.0253(13) -0.0009(11) -0.0034(11) 0.0006(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 1.4491(17) . ? S1 O2 1.4536(16) . ? S1 O3 1.4543(17) . ? S1 C3 1.769(2) . ? S2 O4 1.4422(16) . ? S2 O6 1.4558(17) . ? S2 O5 1.4627(16) . ? S2 C15 1.774(3) . ? N1 C1 1.339(3) . ? N2 C1 1.323(3) . ? N2 C2 1.451(3) . ? N3 C1 1.320(3) . ? N4 C13 1.329(3) . ? N5 C13 1.323(3) . ? N5 C14 1.449(3) . ? N6 C13 1.325(3) . ? C3 C4 1.362(3) . ? C3 C12 1.415(3) . ? C4 C5 1.424(3) . ? C5 C10 1.405(4) . ? C5 C6 1.419(4) . ? C6 C7 1.362(4) . ? C7 C8 1.391(5) . ? C8 C9 1.360(4) . ? C9 C10 1.420(4) . ? C10 C11 1.414(4) . ? C11 C12 1.365(4) . ? C15 C24 1.357(3) . ? C15 C16 1.418(3) . ? C16 C17 1.365(4) . ? C17 C18 1.407(4) . ? C18 C23 1.401(4) . ? C18 C19 1.442(4) . ? C19 C20 1.353(4) . ? C20 C21 1.407(5) . ? C21 C22 1.372(4) . ? C22 C23 1.408(4) . ? C23 C24 1.446(4) . ? 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 112.73(10) . . ? O1 S1 O3 112.09(11) . . ? O2 S1 O3 112.19(9) . . ? O1 S1 C3 105.84(10) . . ? O2 S1 C3 107.87(10) . . ? O3 S1 C3 105.56(11) . . ? O4 S2 O6 113.70(10) . . ? O4 S2 O5 112.67(10) . . ? O6 S2 O5 111.00(10) . . ? O4 S2 C15 107.08(11) . . ? O6 S2 C15 105.78(11) . . ? O5 S2 C15 105.98(10) . . ? C1 N2 C2 124.25(19) . . ? C13 N5 C14 124.68(19) . . ? N3 C1 N2 121.3(2) . . ? N3 C1 N1 119.9(2) . . ? N2 C1 N1 118.9(2) . . ? C4 C3 C12 121.0(2) . . ? C4 C3 S1 121.35(18) . . ? C12 C3 S1 117.62(18) . . ? C3 C4 C5 119.9(2) . . ? C10 C5 C6 119.0(2) . . ? C10 C5 C4 119.3(2) . . ? C6 C5 C4 121.7(2) . . ? C7 C6 C5 120.4(3) . . ? C6 C7 C8 120.7(3) . . ? C9 C8 C7 120.6(3) . . ? C8 C9 C10 120.5(3) . . ? C5 C10 C11 119.1(2) . . ? C5 C10 C9 118.8(3) . . ? C11 C10 C9 122.0(3) . . ? C12 C11 C10 121.0(2) . . ? C11 C12 C3 119.5(2) . . ? N5 C13 N6 121.3(2) . . ? N5 C13 N4 118.8(2) . . ? N6 C13 N4 120.0(2) . . ? C24 C15 C16 120.8(2) . . ? C24 C15 S2 120.71(19) . . ? C16 C15 S2 118.49(19) . . ? C17 C16 C15 120.5(3) . . ? C16 C17 C18 120.0(3) . . ? C23 C18 C17 120.6(3) . . ? C23 C18 C19 118.4(3) . . ? C17 C18 C19 120.9(3) . . ? C20 C19 C18 119.7(3) . . ? C19 C20 C21 121.2(3) . . ? C22 C21 C20 120.5(3) . . ? C21 C22 C23 119.5(3) . . ? C18 C23 C22 120.7(3) . . ? C18 C23 C24 118.4(2) . . ? C22 C23 C24 121.0(2) . . ? C15 C24 C23 119.8(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.325 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.066 #===END data_compound_2b_bath76 _database_code_depnum_ccdc_archive 'CCDC 604282' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 N3 O3 S' _chemical_formula_weight 295.36 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.581(4) _cell_length_b 30.358(11) _cell_length_c 8.693(3) _cell_angle_alpha 90.00 _cell_angle_beta 125.803(19) _cell_angle_gamma 90.00 _cell_volume 2906.8(16) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description flake _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.005 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9888 _exptl_absorpt_correction_T_max 0.9997 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68940 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4970 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 29.54 _reflns_number_total 4655 _reflns_number_gt 3983 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT V7.06a' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0803P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(8) _refine_ls_number_reflns 4655 _refine_ls_number_parameters 362 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.90726(7) 0.59121(2) 0.78549(13) 0.0224(2) Uani 1 1 d . . . S2 S 1.37014(7) 0.61343(3) 0.75138(14) 0.0237(2) Uani 1 1 d . . . O1 O 0.8095(2) 0.59404(8) 0.8093(4) 0.0286(7) Uani 1 1 d . . . O2 O 0.8616(2) 0.58395(8) 0.5879(4) 0.0263(7) Uani 1 1 d . . . O3 O 1.0002(2) 0.55915(8) 0.9120(4) 0.0302(7) Uani 1 1 d . . . O4 O 1.2860(2) 0.59375(8) 0.7868(4) 0.0283(7) Uani 1 1 d . . . O5 O 1.3534(2) 0.59473(9) 0.5837(5) 0.0342(7) Uani 1 1 d . . . O6 O 1.4949(2) 0.61253(9) 0.9169(5) 0.0362(8) Uani 1 1 d . . . N1 N 0.5483(3) 0.57977(9) 0.5122(5) 0.0259(8) Uani 1 1 d . . . H1A H 0.4929 0.5740 0.5316 0.031 Uiso 1 1 calc R . . H1B H 0.6245 0.5836 0.6093 0.031 Uiso 1 1 calc R . . N2 N 0.6010(3) 0.59114(9) 0.3072(5) 0.0269(8) Uani 1 1 d . . . H2A H 0.5803 0.5929 0.1907 0.032 Uiso 1 1 calc R . . H2B H 0.6771 0.5949 0.4043 0.032 Uiso 1 1 calc R . . N3 N 0.4031(3) 0.57726(10) 0.1877(5) 0.0282(8) Uani 1 1 d . . . H3 H 0.3855 0.5833 0.0751 0.034 Uiso 1 1 calc R . . N4 N 1.0401(3) 0.55822(10) 0.5097(6) 0.0311(9) Uani 1 1 d . . . H4A H 0.9845 0.5531 0.5294 0.037 Uiso 1 1 calc R . . H4B H 1.1155 0.5636 0.6061 0.037 Uiso 1 1 calc R . . N5 N 1.0956(3) 0.56563(11) 0.3071(6) 0.0353(9) Uani 1 1 d . . . H5A H 1.1709 0.5710 0.4041 0.042 Uiso 1 1 calc R . . H5B H 1.0761 0.5654 0.1912 0.042 Uiso 1 1 calc R . . N6 N 0.8975(3) 0.54983(9) 0.1873(5) 0.0253(7) Uani 1 1 d . . . H6 H 0.8804 0.5532 0.0735 0.030 Uiso 1 1 calc R . . C1 C 0.9801(3) 0.64285(10) 0.8484(6) 0.0215(8) Uani 1 1 d . . . C2 C 1.0902(3) 0.64701(11) 0.8650(7) 0.0300(10) Uani 1 1 d . . . H2 H 1.1233 0.6220 0.8445 0.036 Uiso 1 1 calc R . . C3 C 1.1485(3) 0.68631(11) 0.9099(7) 0.0307(10) Uani 1 1 d . . . H3A H 1.2239 0.6882 0.9260 0.037 Uiso 1 1 calc R . . C4 C 1.0983(3) 0.72474(11) 0.9330(6) 0.0257(9) Uani 1 1 d . . . C5 C 1.1545(4) 0.76654(12) 0.9734(7) 0.0367(11) Uani 1 1 d . . . H5 H 1.2299 0.7693 0.9902 0.044 Uiso 1 1 calc R . . C6 C 1.1012(4) 0.80299(12) 0.9884(7) 0.0394(12) Uani 1 1 d . . . H6A H 1.1395 0.8309 1.0143 0.047 Uiso 1 1 calc R . . C7 C 0.9898(4) 0.79937(12) 0.9656(7) 0.0394(11) Uani 1 1 d . . . H7 H 0.9534 0.8248 0.9760 0.047 Uiso 1 1 calc R . . C8 C 0.9342(4) 0.75939(11) 0.9287(7) 0.0344(11) Uani 1 1 d . . . H8 H 0.8591 0.7573 0.9133 0.041 Uiso 1 1 calc R . . C9 C 0.9870(3) 0.72079(11) 0.9128(6) 0.0234(9) Uani 1 1 d . . . C10 C 0.9296(3) 0.67909(10) 0.8720(6) 0.0227(8) Uani 1 1 d . . . H10 H 0.8561 0.6762 0.8609 0.027 Uiso 1 1 calc R . . C11 C 1.3252(4) 0.66980(12) 0.6937(8) 0.0353(11) Uani 1 1 d . . . C12 C 1.2191(4) 0.67882(13) 0.5066(7) 0.0380(11) Uani 1 1 d . . . H12 H 1.1770 0.6555 0.4183 0.046 Uiso 1 1 calc R . . C13 C 1.1786(4) 0.72154(13) 0.4561(8) 0.0428(12) Uani 1 1 d . . . H13 H 1.1071 0.7279 0.3338 0.051 Uiso 1 1 calc R . . C14 C 1.2436(4) 0.75521(14) 0.5859(8) 0.0418(13) Uani 1 1 d . . . C15 C 1.2043(4) 0.80159(14) 0.5303(9) 0.0475(14) Uani 1 1 d . . . H15 H 1.1354 0.8088 0.4065 0.057 Uiso 1 1 calc R . . C16 C 1.2699(4) 0.83348(13) 0.6619(8) 0.0409(12) Uani 1 1 d . . . H16 H 1.2465 0.8634 0.6288 0.049 Uiso 1 1 calc R . . C17 C 1.3707(5) 0.82336(15) 0.8446(9) 0.0540(15) Uani 1 1 d . . . H17 H 1.4127 0.8465 0.9340 0.065 Uiso 1 1 calc R . . C18 C 1.4103(4) 0.78114(14) 0.8977(8) 0.0437(12) Uani 1 1 d . . . H18 H 1.4812 0.7750 1.0209 0.052 Uiso 1 1 calc R . . C19 C 1.3463(4) 0.74749(13) 0.7706(7) 0.0383(12) Uani 1 1 d . . . C20 C 1.3873(4) 0.70171(13) 0.8224(8) 0.0399(12) Uani 1 1 d . . . H20 H 1.4570 0.6947 0.9458 0.048 Uiso 1 1 calc R . . C21 C 0.5170(3) 0.58281(10) 0.3364(6) 0.0239(10) Uani 1 1 d . . . C22 C 0.3039(3) 0.56186(12) 0.1961(6) 0.0275(9) Uani 1 1 d . . . H22A H 0.2259 0.5657 0.0698 0.033 Uiso 1 1 calc R . . H22B H 0.3012 0.5803 0.2874 0.033 Uiso 1 1 calc R . . C23 C 0.3167(4) 0.51418(14) 0.2546(8) 0.0492(14) Uani 1 1 d . . . H23A H 0.2481 0.5058 0.2573 0.074 Uiso 1 1 calc R . . H23B H 0.3927 0.5102 0.3811 0.074 Uiso 1 1 calc R . . H23C H 0.3177 0.4956 0.1634 0.074 Uiso 1 1 calc R . . C24 C 1.0104(3) 0.55783(11) 0.3361(7) 0.0265(10) Uani 1 1 d . . . C25 C 0.7998(3) 0.53576(11) 0.2005(6) 0.0250(9) Uani 1 1 d . . . H25A H 0.7808 0.5597 0.2565 0.030 Uiso 1 1 calc R . . H25B H 0.8264 0.5097 0.2845 0.030 Uiso 1 1 calc R . . C26 C 0.6885(3) 0.52442(13) 0.0078(7) 0.0369(11) Uani 1 1 d . . . H26A H 0.6236 0.5152 0.0187 0.055 Uiso 1 1 calc R . . H26B H 0.7071 0.5003 -0.0464 0.055 Uiso 1 1 calc R . . H26C H 0.6620 0.5503 -0.0750 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0179(3) 0.0303(4) 0.0176(7) -0.0011(4) 0.0097(4) -0.0033(3) S2 0.0206(4) 0.0324(4) 0.0195(7) -0.0010(4) 0.0124(4) -0.0007(3) O1 0.0261(12) 0.0419(13) 0.025(2) -0.0068(12) 0.0192(14) -0.0093(9) O2 0.0213(12) 0.0461(14) 0.008(2) -0.0062(11) 0.0063(13) -0.0054(9) O3 0.0291(12) 0.0308(12) 0.020(2) 0.0015(11) 0.0083(13) -0.0015(9) O4 0.0299(13) 0.0346(12) 0.027(2) 0.0025(11) 0.0203(14) -0.0036(9) O5 0.0345(14) 0.0499(15) 0.023(2) -0.0089(13) 0.0194(15) -0.0055(11) O6 0.0239(13) 0.0543(16) 0.024(2) 0.0010(13) 0.0103(14) -0.0024(11) N1 0.0218(14) 0.0378(15) 0.019(3) 0.0014(13) 0.0127(16) -0.0004(11) N2 0.0184(13) 0.0491(16) 0.012(2) 0.0007(14) 0.0080(15) -0.0014(11) N3 0.0215(15) 0.0493(17) 0.012(3) 0.0062(14) 0.0091(16) -0.0003(12) N4 0.0199(14) 0.0498(18) 0.021(3) -0.0052(14) 0.0107(17) -0.0019(12) N5 0.0224(15) 0.067(2) 0.016(3) -0.0097(16) 0.0110(17) -0.0107(14) N6 0.0238(15) 0.0428(16) 0.010(2) -0.0013(14) 0.0100(16) -0.0058(12) C1 0.0176(15) 0.0312(16) 0.013(3) 0.0026(13) 0.0070(17) 0.0009(11) C2 0.0248(17) 0.0327(16) 0.036(3) -0.0027(16) 0.020(2) 0.0016(12) C3 0.0244(17) 0.0347(17) 0.042(3) -0.0026(16) 0.024(2) -0.0017(12) C4 0.0258(17) 0.0340(17) 0.018(3) 0.0026(14) 0.0136(19) 0.0007(12) C5 0.0319(19) 0.0380(19) 0.042(4) -0.0003(18) 0.023(2) -0.0055(14) C6 0.043(2) 0.0319(18) 0.041(4) -0.0047(18) 0.023(2) -0.0067(15) C7 0.045(2) 0.0327(18) 0.044(4) 0.0014(18) 0.028(2) 0.0056(15) C8 0.034(2) 0.0356(18) 0.042(4) 0.0023(17) 0.027(2) 0.0066(14) C9 0.0192(15) 0.0330(16) 0.017(3) 0.0001(14) 0.0102(18) -0.0002(12) C10 0.0194(15) 0.0331(16) 0.019(3) 0.0023(14) 0.0135(18) 0.0002(11) C11 0.0333(19) 0.0364(19) 0.050(4) -0.0034(18) 0.032(2) -0.0046(14) C12 0.036(2) 0.046(2) 0.033(4) 0.0021(18) 0.020(2) 0.0013(15) C13 0.034(2) 0.049(2) 0.042(4) 0.003(2) 0.021(2) 0.0000(16) C14 0.036(2) 0.050(2) 0.058(4) -0.020(2) 0.038(3) -0.0167(16) C15 0.036(2) 0.050(2) 0.064(5) -0.002(2) 0.034(3) 0.0018(18) C16 0.045(2) 0.0323(19) 0.050(4) 0.0003(19) 0.030(3) 0.0038(15) C17 0.065(3) 0.048(2) 0.067(5) -0.010(2) 0.049(4) -0.002(2) C18 0.046(2) 0.048(2) 0.040(4) -0.006(2) 0.027(3) -0.0031(18) C19 0.027(2) 0.056(2) 0.039(4) 0.006(2) 0.023(2) -0.0030(16) C20 0.033(2) 0.046(2) 0.053(4) -0.010(2) 0.032(3) -0.0063(15) C21 0.0224(17) 0.0282(15) 0.020(3) 0.0019(14) 0.0114(19) 0.0011(11) C22 0.0163(15) 0.0445(19) 0.019(3) 0.0016(16) 0.0088(18) -0.0015(12) C23 0.040(2) 0.046(2) 0.066(5) -0.007(2) 0.033(3) -0.0094(16) C24 0.0250(18) 0.0360(18) 0.018(4) -0.0014(15) 0.012(2) -0.0028(12) C25 0.0231(16) 0.0321(16) 0.022(3) 0.0009(15) 0.0142(19) -0.0019(12) C26 0.031(2) 0.045(2) 0.036(4) -0.0050(18) 0.020(2) -0.0083(15) _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 O3 1.458(3) . ? S1 O1 1.461(2) . ? S1 O2 1.462(3) . ? S1 C1 1.761(3) . ? S2 O6 1.446(3) . ? S2 O5 1.453(3) . ? S2 O4 1.473(2) . ? S2 C11 1.787(4) . ? N1 C21 1.328(5) . ? N2 C21 1.329(4) . ? N3 C21 1.324(5) . ? N3 C22 1.468(4) . ? N4 C24 1.314(5) . ? N5 C24 1.341(4) . ? N6 C24 1.328(5) . ? N6 C25 1.461(4) . ? C1 C10 1.373(4) . ? C1 C2 1.422(4) . ? C2 C3 1.357(5) . ? C3 C4 1.424(5) . ? C4 C5 1.415(5) . ? C4 C9 1.422(4) . ? C5 C6 1.370(5) . ? C6 C7 1.411(5) . ? C7 C8 1.365(5) . ? C8 C9 1.421(5) . ? C9 C10 1.418(4) . ? C11 C20 1.341(6) . ? C11 C12 1.433(7) . ? C12 C13 1.376(6) . ? C13 C14 1.390(6) . ? C14 C19 1.399(7) . ? C14 C15 1.483(6) . ? C15 C16 1.359(7) . ? C16 C17 1.395(8) . ? C17 C18 1.362(6) . ? C18 C19 1.377(7) . ? C19 C20 1.467(6) . ? C22 C23 1.510(6) . ? C25 C26 1.499(6) . ? 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 O3 S1 O1 112.97(17) . . ? O3 S1 O2 111.74(16) . . ? O1 S1 O2 112.27(16) . . ? O3 S1 C1 106.18(16) . . ? O1 S1 C1 107.20(15) . . ? O2 S1 C1 105.92(17) . . ? O6 S2 O5 113.31(17) . . ? O6 S2 O4 112.66(18) . . ? O5 S2 O4 111.46(16) . . ? O6 S2 C11 107.9(2) . . ? O5 S2 C11 105.4(2) . . ? O4 S2 C11 105.51(15) . . ? C21 N3 C22 125.1(4) . . ? C24 N6 C25 124.1(4) . . ? C10 C1 C2 120.1(3) . . ? C10 C1 S1 121.4(2) . . ? C2 C1 S1 118.5(2) . . ? C3 C2 C1 120.6(3) . . ? C2 C3 C4 120.9(3) . . ? C5 C4 C9 119.1(3) . . ? C5 C4 C3 122.4(3) . . ? C9 C4 C3 118.4(3) . . ? C6 C5 C4 120.6(3) . . ? C5 C6 C7 120.4(4) . . ? C8 C7 C6 120.2(3) . . ? C7 C8 C9 121.0(3) . . ? C10 C9 C8 121.8(3) . . ? C10 C9 C4 119.6(3) . . ? C8 C9 C4 118.6(3) . . ? C1 C10 C9 120.2(3) . . ? C20 C11 C12 122.2(4) . . ? C20 C11 S2 120.8(4) . . ? C12 C11 S2 116.9(3) . . ? C13 C12 C11 119.4(4) . . ? C12 C13 C14 119.2(5) . . ? C13 C14 C19 122.8(4) . . ? C13 C14 C15 119.8(5) . . ? C19 C14 C15 117.4(4) . . ? C16 C15 C14 117.9(5) . . ? C15 C16 C17 121.6(4) . . ? C18 C17 C16 121.5(5) . . ? C17 C18 C19 119.2(5) . . ? C18 C19 C14 122.3(4) . . ? C18 C19 C20 120.5(5) . . ? C14 C19 C20 117.1(4) . . ? C11 C20 C19 119.2(5) . . ? N3 C21 N1 121.3(3) . . ? N3 C21 N2 118.7(4) . . ? N1 C21 N2 120.0(3) . . ? N3 C22 C23 113.2(3) . . ? N4 C24 N6 121.6(3) . . ? N4 C24 N5 119.7(4) . . ? N6 C24 N5 118.7(4) . . ? N6 C25 C26 110.4(3) . . ? _diffrn_measured_fraction_theta_max 0.694 _diffrn_reflns_theta_full 29.54 _diffrn_measured_fraction_theta_full 0.694 _refine_diff_density_max 0.514 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.056 #===END data_compound_2c_bath77 _database_code_depnum_ccdc_archive 'CCDC 604283' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 N3 O3 S' _chemical_formula_weight 295.36 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 54.44(3) _cell_length_b 10.652(4) _cell_length_c 10.105(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5860(4) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2496 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68940 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18809 _diffrn_reflns_av_R_equivalents 0.0998 _diffrn_reflns_av_sigmaI/netI 0.0818 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 74 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 29.57 _reflns_number_total 8026 _reflns_number_gt 5251 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT V7.06a' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0806P)^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 8026 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0990 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1685 _refine_ls_wR_factor_gt 0.1528 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.044395(11) 0.53680(5) 0.74739(6) 0.02324(14) Uani 1 1 d . . . S2 S 0.205524(10) 0.51354(5) 0.55765(5) 0.01938(13) Uani 1 1 d . . . O1 O 0.02908(3) 0.59692(16) 0.84841(15) 0.0262(4) Uani 1 1 d . . . O2 O 0.04261(3) 0.60394(16) 0.62130(16) 0.0304(4) Uani 1 1 d . . . O3 O 0.04046(4) 0.40352(17) 0.73520(19) 0.0382(5) Uani 1 1 d . . . O4 O 0.21019(3) 0.59448(16) 0.44371(16) 0.0284(4) Uani 1 1 d . . . O5 O 0.20181(3) 0.58901(16) 0.67730(15) 0.0262(4) Uani 1 1 d . . . O6 O 0.22357(3) 0.41553(16) 0.5748(2) 0.0332(4) Uani 1 1 d . . . N1 N 0.02683(4) 0.86883(19) 0.85493(19) 0.0287(5) Uani 1 1 d . . . H1B H 0.0264 0.9096 0.9306 0.034 Uiso 1 1 calc R . . H1A H 0.0263 0.7863 0.8541 0.034 Uiso 1 1 calc R . . N2 N 0.02900(4) 0.86751(19) 0.62802(18) 0.0279(5) Uani 1 1 d . . . H2B H 0.0300 0.9073 0.5519 0.033 Uiso 1 1 calc R . . H2A H 0.0284 0.7850 0.6297 0.033 Uiso 1 1 calc R . . N3 N 0.02922(4) 1.05708(18) 0.74051(19) 0.0232(4) Uani 1 1 d . . . N4 N 0.21776(4) 0.86335(18) 0.44202(19) 0.0245(4) Uani 1 1 d . . . H4B H 0.2184 0.9055 0.3672 0.029 Uiso 1 1 calc R . . H4A H 0.2160 0.7812 0.4409 0.029 Uiso 1 1 calc R . . N5 N 0.21850(4) 0.85712(17) 0.66953(18) 0.0217(4) Uani 1 1 d . . . H5B H 0.2196 0.8951 0.7466 0.026 Uiso 1 1 calc R . . H5A H 0.2167 0.7751 0.6660 0.026 Uiso 1 1 calc R . . N6 N 0.22223(4) 1.04813(17) 0.56122(18) 0.0197(4) Uani 1 1 d . . . C1 C 0.07527(5) 0.5555(2) 0.7999(2) 0.0236(5) Uani 1 1 d . . . C2 C 0.09385(5) 0.4889(3) 0.7301(3) 0.0349(6) Uani 1 1 d . . . H2 H 0.0897 0.4370 0.6569 0.042 Uiso 1 1 calc R . . C3 C 0.11800(6) 0.5003(3) 0.7696(3) 0.0387(7) Uani 1 1 d . . . H3 H 0.1304 0.4562 0.7228 0.046 Uiso 1 1 calc R . . C4 C 0.12463(5) 0.5766(3) 0.8787(3) 0.0311(6) Uani 1 1 d . . . C5 C 0.14964(5) 0.5898(3) 0.9214(3) 0.0444(7) Uani 1 1 d . . . H5 H 0.1623 0.5449 0.8773 0.053 Uiso 1 1 calc R . . C6 C 0.15526(6) 0.6656(4) 1.0238(3) 0.0493(8) Uani 1 1 d . . . H6 H 0.1719 0.6726 1.0518 0.059 Uiso 1 1 calc R . . C7 C 0.13698(5) 0.7345(4) 1.0899(3) 0.0483(8) Uani 1 1 d . . . H7 H 0.1414 0.7884 1.1610 0.058 Uiso 1 1 calc R . . C8 C 0.11275(5) 0.7243(3) 1.0521(3) 0.0424(7) Uani 1 1 d . . . H8 H 0.1005 0.7703 1.0979 0.051 Uiso 1 1 calc R . . C9 C 0.10617(5) 0.6455(2) 0.9453(2) 0.0279(5) Uani 1 1 d . . . C10 C 0.08128(4) 0.6321(2) 0.9035(2) 0.0264(5) Uani 1 1 d . . . H10 H 0.0687 0.6770 0.9483 0.032 Uiso 1 1 calc R . . C11 C 0.17708(4) 0.4373(2) 0.5251(2) 0.0228(5) Uani 1 1 d . . . C12 C 0.17189(5) 0.3220(2) 0.5892(3) 0.0315(6) Uani 1 1 d . . . H12 H 0.1836 0.2860 0.6476 0.038 Uiso 1 1 calc R . . C13 C 0.14998(5) 0.2624(3) 0.5669(3) 0.0423(7) Uani 1 1 d . . . H13 H 0.1467 0.1847 0.6097 0.051 Uiso 1 1 calc R . . C14 C 0.13216(5) 0.3139(3) 0.4819(3) 0.0410(7) Uani 1 1 d . . . C15 C 0.10886(6) 0.2558(4) 0.4576(4) 0.0614(11) Uani 1 1 d . . . H15 H 0.1051 0.1785 0.4999 0.074 Uiso 1 1 calc R . . C16 C 0.09210(6) 0.3081(5) 0.3763(5) 0.0737(14) Uani 1 1 d . . . H16 H 0.0769 0.2665 0.3610 0.088 Uiso 1 1 calc R . . C17 C 0.09677(7) 0.4219(5) 0.3148(5) 0.0777(14) Uani 1 1 d . . . H17 H 0.0847 0.4581 0.2584 0.093 Uiso 1 1 calc R . . C18 C 0.11888(6) 0.4829(4) 0.3350(4) 0.0596(10) Uani 1 1 d . . . H18 H 0.1219 0.5612 0.2930 0.072 Uiso 1 1 calc R . . C19 C 0.13707(5) 0.4296(3) 0.4179(3) 0.0398(7) Uani 1 1 d . . . C20 C 0.16019(5) 0.4896(3) 0.4413(3) 0.0331(6) Uani 1 1 d . . . H20 H 0.1639 0.5666 0.3982 0.040 Uiso 1 1 calc R . . C21 C 0.02836(4) 0.9324(2) 0.7410(2) 0.0215(4) Uani 1 1 d . . . C22 C 0.03203(5) 1.1246(2) 0.6151(2) 0.0299(6) Uani 1 1 d . . . H22A H 0.0462 1.0911 0.5669 0.045 Uiso 1 1 calc R . . H22B H 0.0346 1.2141 0.6330 0.045 Uiso 1 1 calc R . . H22C H 0.0172 1.1138 0.5616 0.045 Uiso 1 1 calc R . . C23 C 0.02454(5) 1.1267(2) 0.8635(2) 0.0296(5) Uani 1 1 d . . . H23A H 0.0088 1.1003 0.9009 0.044 Uiso 1 1 calc R . . H23B H 0.0240 1.2169 0.8444 0.044 Uiso 1 1 calc R . . H23C H 0.0377 1.1095 0.9271 0.044 Uiso 1 1 calc R . . C24 C 0.21955(4) 0.9241(2) 0.5576(2) 0.0181(4) Uani 1 1 d . . . C25 C 0.22429(5) 1.1199(2) 0.4380(2) 0.0284(5) Uani 1 1 d . . . H25A H 0.2389 1.0925 0.3892 0.043 Uiso 1 1 calc R . . H25B H 0.2257 1.2095 0.4586 0.043 Uiso 1 1 calc R . . H25C H 0.2096 1.1058 0.3837 0.043 Uiso 1 1 calc R . . C26 C 0.22693(5) 1.1112(2) 0.6876(2) 0.0265(5) Uani 1 1 d . . . H26A H 0.2128 1.0992 0.7465 0.040 Uiso 1 1 calc R . . H26B H 0.2294 1.2011 0.6721 0.040 Uiso 1 1 calc R . . H26C H 0.2417 1.0754 0.7286 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0326(3) 0.0199(3) 0.0172(3) -0.0009(2) -0.0034(2) -0.0011(2) S2 0.0245(3) 0.0178(2) 0.0159(3) -0.00061(19) -0.0005(2) -0.0012(2) O1 0.0281(9) 0.0320(9) 0.0185(8) 0.0000(7) -0.0032(7) -0.0015(7) O2 0.0444(11) 0.0314(9) 0.0153(8) 0.0021(7) -0.0029(7) 0.0023(8) O3 0.0505(12) 0.0211(9) 0.0429(11) -0.0036(8) -0.0069(9) -0.0066(8) O4 0.0431(10) 0.0268(8) 0.0152(8) 0.0009(7) 0.0025(7) -0.0082(8) O5 0.0381(10) 0.0262(8) 0.0142(8) -0.0046(6) -0.0018(7) -0.0054(7) O6 0.0260(9) 0.0227(8) 0.0509(12) 0.0009(8) -0.0022(8) 0.0021(7) N1 0.0440(13) 0.0246(10) 0.0175(10) 0.0019(8) -0.0023(9) -0.0002(9) N2 0.0479(13) 0.0214(10) 0.0144(9) -0.0008(8) -0.0017(9) -0.0030(9) N3 0.0296(11) 0.0222(9) 0.0179(9) 0.0006(8) -0.0011(8) -0.0015(8) N4 0.0378(12) 0.0204(9) 0.0153(9) 0.0003(8) -0.0019(8) -0.0015(8) N5 0.0310(11) 0.0175(9) 0.0165(9) 0.0002(7) -0.0017(8) -0.0006(8) N6 0.0271(10) 0.0179(8) 0.0141(9) 0.0012(7) 0.0001(7) 0.0014(7) C1 0.0324(13) 0.0198(11) 0.0184(11) 0.0024(9) 0.0019(9) -0.0008(9) C2 0.0417(16) 0.0360(14) 0.0271(13) -0.0063(11) 0.0034(11) 0.0041(12) C3 0.0376(16) 0.0425(15) 0.0360(15) -0.0059(12) 0.0063(12) 0.0116(12) C4 0.0314(14) 0.0345(13) 0.0274(13) 0.0009(11) 0.0043(11) 0.0039(11) C5 0.0285(15) 0.0555(19) 0.0493(18) -0.0006(15) 0.0024(13) 0.0072(13) C6 0.0262(15) 0.072(2) 0.0493(18) 0.0002(17) -0.0011(13) -0.0041(15) C7 0.0335(15) 0.066(2) 0.0457(18) -0.0165(16) -0.0044(13) -0.0109(15) C8 0.0305(14) 0.0566(19) 0.0402(16) -0.0156(14) 0.0016(12) -0.0059(13) C9 0.0285(13) 0.0311(12) 0.0242(12) -0.0003(10) 0.0029(10) -0.0012(10) C10 0.0261(12) 0.0281(12) 0.0249(12) -0.0042(10) 0.0043(9) 0.0004(10) C11 0.0244(12) 0.0234(11) 0.0206(11) -0.0047(9) 0.0005(9) 0.0008(9) C12 0.0305(13) 0.0237(12) 0.0402(15) 0.0015(11) 0.0036(11) -0.0012(10) C13 0.0348(15) 0.0297(13) 0.062(2) -0.0059(14) 0.0086(14) -0.0067(12) C14 0.0262(14) 0.0405(16) 0.0562(19) -0.0220(14) 0.0044(12) -0.0043(12) C15 0.0305(16) 0.058(2) 0.096(3) -0.040(2) 0.0094(17) -0.0095(15) C16 0.0289(18) 0.084(3) 0.109(3) -0.053(3) -0.011(2) -0.0022(18) C17 0.039(2) 0.107(4) 0.087(3) -0.035(3) -0.030(2) 0.013(2) C18 0.0446(19) 0.072(2) 0.062(2) -0.0103(19) -0.0262(17) 0.0081(17) C19 0.0275(14) 0.0520(18) 0.0399(16) -0.0138(14) -0.0063(11) 0.0018(12) C20 0.0331(14) 0.0363(14) 0.0298(14) -0.0028(11) -0.0051(11) -0.0003(11) C21 0.0225(11) 0.0245(11) 0.0173(10) -0.0006(9) -0.0018(8) 0.0009(8) C22 0.0455(15) 0.0224(12) 0.0218(12) 0.0029(9) 0.0025(11) -0.0046(10) C23 0.0392(15) 0.0253(12) 0.0244(12) -0.0067(10) 0.0030(10) -0.0015(10) C24 0.0198(10) 0.0195(10) 0.0151(10) -0.0001(8) -0.0007(8) 0.0007(8) C25 0.0413(15) 0.0230(11) 0.0209(12) 0.0041(9) 0.0034(10) 0.0001(10) C26 0.0407(15) 0.0194(11) 0.0193(11) -0.0017(9) -0.0051(10) -0.0003(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.4411(19) . ? S1 O2 1.4644(17) . ? S1 O1 1.4654(18) . ? S1 C1 1.774(3) . ? S2 O6 1.4441(18) . ? S2 O4 1.4607(17) . ? S2 O5 1.4660(16) . ? S2 C11 1.779(2) . ? N1 C21 1.338(3) . ? N2 C21 1.335(3) . ? N3 C21 1.329(3) . ? N3 C22 1.465(3) . ? N3 C23 1.470(3) . ? N4 C24 1.339(3) . ? N5 C24 1.338(3) . ? N6 C24 1.330(3) . ? N6 C26 1.465(3) . ? N6 C25 1.466(3) . ? C1 C10 1.367(3) . ? C1 C2 1.423(4) . ? C2 C3 1.380(4) . ? C3 C4 1.415(4) . ? C4 C9 1.415(3) . ? C4 C5 1.435(4) . ? C5 C6 1.348(4) . ? C6 C7 1.405(5) . ? C7 C8 1.378(4) . ? C8 C9 1.414(4) . ? C9 C10 1.426(4) . ? C11 C20 1.369(3) . ? C11 C12 1.417(3) . ? C12 C13 1.370(4) . ? C13 C14 1.407(4) . ? C14 C19 1.417(5) . ? C14 C15 1.432(4) . ? C15 C16 1.349(6) . ? C16 C17 1.385(7) . ? C17 C18 1.383(5) . ? C18 C19 1.416(4) . ? C19 C20 1.432(4) . ? 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 O3 S1 O2 113.39(11) . . ? O3 S1 O1 113.93(11) . . ? O2 S1 O1 110.79(10) . . ? O3 S1 C1 106.09(12) . . ? O2 S1 C1 105.55(11) . . ? O1 S1 C1 106.36(11) . . ? O6 S2 O4 113.77(11) . . ? O6 S2 O5 113.05(11) . . ? O4 S2 O5 110.51(10) . . ? O6 S2 C11 106.52(11) . . ? O4 S2 C11 105.96(11) . . ? O5 S2 C11 106.41(10) . . ? C21 N3 C22 119.86(19) . . ? C21 N3 C23 119.68(19) . . ? C22 N3 C23 120.09(19) . . ? C24 N6 C26 119.89(18) . . ? C24 N6 C25 120.24(19) . . ? C26 N6 C25 119.21(18) . . ? C10 C1 C2 120.5(2) . . ? C10 C1 S1 121.52(19) . . ? C2 C1 S1 117.98(19) . . ? C3 C2 C1 119.3(3) . . ? C2 C3 C4 121.3(3) . . ? C9 C4 C3 119.1(2) . . ? C9 C4 C5 118.7(3) . . ? C3 C4 C5 122.2(3) . . ? C6 C5 C4 120.3(3) . . ? C5 C6 C7 121.1(3) . . ? C8 C7 C6 120.3(3) . . ? C7 C8 C9 120.1(3) . . ? C8 C9 C4 119.4(2) . . ? C8 C9 C10 121.8(2) . . ? C4 C9 C10 118.8(2) . . ? C1 C10 C9 120.9(2) . . ? C20 C11 C12 120.1(2) . . ? C20 C11 S2 120.88(19) . . ? C12 C11 S2 118.99(19) . . ? C13 C12 C11 120.0(3) . . ? C12 C13 C14 121.4(3) . . ? C13 C14 C19 119.2(3) . . ? C13 C14 C15 123.2(3) . . ? C19 C14 C15 117.6(3) . . ? C16 C15 C14 121.7(4) . . ? C15 C16 C17 120.7(3) . . ? C18 C17 C16 120.3(4) . . ? C17 C18 C19 120.5(4) . . ? C18 C19 C14 119.1(3) . . ? C18 C19 C20 122.2(3) . . ? C14 C19 C20 118.6(3) . . ? C11 C20 C19 120.7(3) . . ? N3 C21 N2 120.9(2) . . ? N3 C21 N1 120.8(2) . . ? N2 C21 N1 118.4(2) . . ? N6 C24 N5 120.7(2) . . ? N6 C24 N4 120.8(2) . . ? N5 C24 N4 118.45(19) . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.892 _refine_diff_density_max 0.483 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.098 #===END data_compound_3a_h05njb3 _database_code_depnum_ccdc_archive 'CCDC 604284' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H23 N3 O4 S' _chemical_formula_weight 305.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 13.0450(2) _cell_length_b 13.7180(2) _cell_length_c 17.8470(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3193.74(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21597 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.922 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34543 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 24.99 _reflns_number_total 5567 _reflns_number_gt 4429 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.1613P)^2^+0.7090P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.029(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(15) _refine_ls_number_reflns 5567 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.2357 _refine_ls_wR_factor_gt 0.2162 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.96383(9) 0.05725(9) 0.08816(6) 0.0648(4) Uani 1 1 d . . . S2 S 0.52024(8) 0.44302(8) 0.40940(6) 0.0546(3) Uani 1 1 d . . . O1 O 1.0002(4) 0.1502(3) 0.0677(2) 0.1003(14) Uani 1 1 d . . . O2 O 0.8552(3) 0.0492(3) 0.0823(3) 0.1060(14) Uani 1 1 d . . . O3 O 1.0100(4) -0.0232(4) 0.0441(3) 0.1124(16) Uani 1 1 d . . . O4 O 0.6303(2) 0.4465(2) 0.4183(2) 0.0721(8) Uani 1 1 d . . . O5 O 0.4791(3) 0.3462(2) 0.4253(2) 0.0688(9) Uani 1 1 d . . . O6 O 0.4693(3) 0.5192(3) 0.4517(2) 0.0878(11) Uani 1 1 d . . . O7 O 1.1419(5) 0.1976(6) 0.1955(4) 0.152(2) Uani 1 1 d . . . O8 O 0.6397(9) 0.5477(7) 0.2140(9) 0.278(8) Uani 1 1 d . . . N1 N 0.9023(3) 0.3281(3) 0.0131(3) 0.0779(11) Uani 1 1 d . . . H1B H 0.9292 0.3840 0.0035 0.093 Uiso 1 1 calc R . . H1A H 0.9352 0.2864 0.0398 0.093 Uiso 1 1 calc R . . N2 N 0.7695(3) 0.2216(3) 0.0041(3) 0.0741(11) Uani 1 1 d . . . H2A H 0.8032 0.1849 0.0344 0.089 Uiso 1 1 calc R . . N3 N 0.7606(3) 0.3698(3) -0.0539(3) 0.0866(14) Uani 1 1 d . . . H3A H 0.6999 0.3567 -0.0697 0.104 Uiso 1 1 calc R . . H3B H 0.7886 0.4248 -0.0648 0.104 Uiso 1 1 calc R . . N4 N 0.7333(3) 0.2896(3) 0.4912(3) 0.0714(11) Uani 1 1 d . . . H4A H 0.6956 0.3285 0.4652 0.086 Uiso 1 1 calc R . . N5 N 0.6025(3) 0.1797(3) 0.4809(3) 0.0726(11) Uani 1 1 d . . . H5A H 0.5664 0.2225 0.4577 0.087 Uiso 1 1 calc R . . H5B H 0.5778 0.1226 0.4891 0.087 Uiso 1 1 calc R . . N6 N 0.7518(3) 0.1355(3) 0.5416(3) 0.0724(11) Uani 1 1 d . . . H6A H 0.8121 0.1500 0.5575 0.087 Uiso 1 1 calc R . . H6B H 0.7270 0.0784 0.5497 0.087 Uiso 1 1 calc R . . C1 C 0.8103(4) 0.3063(3) -0.0134(3) 0.0624(11) Uani 1 1 d . . . C2 C 0.6736(5) 0.1858(4) -0.0232(5) 0.101(2) Uani 1 1 d . . . H2C H 0.6186 0.2210 0.0002 0.151 Uiso 1 1 calc R . . H2D H 0.6675 0.1177 -0.0115 0.151 Uiso 1 1 calc R . . H2E H 0.6703 0.1946 -0.0765 0.151 Uiso 1 1 calc R . . C3 C 0.6966(3) 0.2018(3) 0.5042(2) 0.0562(10) Uani 1 1 d . . . C4 C 0.8297(5) 0.3263(4) 0.5163(5) 0.109(2) Uani 1 1 d . . . H4C H 0.8352 0.3177 0.5696 0.164 Uiso 1 1 calc R . . H4D H 0.8346 0.3944 0.5045 0.164 Uiso 1 1 calc R . . H4E H 0.8841 0.2916 0.4918 0.164 Uiso 1 1 calc R . . C5 C 1.0041(5) 0.0314(5) 0.1809(3) 0.0901(17) Uani 1 1 d . . . H5C H 0.9686 -0.0272 0.1969 0.108 Uiso 1 1 calc R . . H5D H 1.0765 0.0156 0.1789 0.108 Uiso 1 1 calc R . . C6 C 0.9902(5) 0.1048(4) 0.2400(3) 0.0781(14) Uani 1 1 d . . . C7 C 1.0799(8) 0.1794(7) 0.2411(5) 0.130(3) Uani 1 1 d . . . C8 C 1.0827(11) 0.2266(8) 0.3141(5) 0.175(5) Uani 1 1 d . . . H8A H 1.0706 0.2962 0.3104 0.209 Uiso 1 1 calc R . . H8B H 1.1470 0.2150 0.3398 0.209 Uiso 1 1 calc R . . C9 C 0.9876(13) 0.1705(9) 0.3545(5) 0.186(6) Uani 1 1 d . . . H9 H 0.9883 0.1708 0.4094 0.224 Uiso 1 1 calc R . . C10 C 0.8808(10) 0.2101(11) 0.3151(7) 0.192(6) Uani 1 1 d . . . H10A H 0.8208 0.1821 0.3390 0.230 Uiso 1 1 calc R . . H10B H 0.8763 0.2806 0.3172 0.230 Uiso 1 1 calc R . . C11 C 0.8917(10) 0.1754(9) 0.2375(5) 0.161(5) Uani 1 1 d . . . H11A H 0.9030 0.2295 0.2034 0.194 Uiso 1 1 calc R . . H11B H 0.8312 0.1400 0.2216 0.194 Uiso 1 1 calc R . . C12 C 0.9875(8) 0.0763(10) 0.3201(4) 0.150(4) Uani 1 1 d . . . C13 C 1.0935(11) 0.0286(9) 0.3483(6) 0.172(5) Uani 1 1 d . . . H13A H 1.1474 0.0760 0.3450 0.258 Uiso 1 1 calc R . . H13B H 1.1100 -0.0265 0.3174 0.258 Uiso 1 1 calc R . . H13C H 1.0862 0.0077 0.3994 0.258 Uiso 1 1 calc R . . C14 C 0.9026(13) 0.0129(11) 0.3424(7) 0.209(7) Uani 1 1 d . . . H14A H 0.9288 -0.0417 0.3700 0.313 Uiso 1 1 calc R . . H14B H 0.8675 -0.0100 0.2985 0.313 Uiso 1 1 calc R . . H14C H 0.8557 0.0489 0.3733 0.313 Uiso 1 1 calc R . . C15 C 0.4954(5) 0.4737(4) 0.3151(3) 0.0812(15) Uani 1 1 d . . . H15A H 0.4216 0.4744 0.3086 0.097 Uiso 1 1 calc R . . H15B H 0.5193 0.5399 0.3075 0.097 Uiso 1 1 calc R . . C16 C 0.5407(4) 0.4108(4) 0.2520(3) 0.0727(13) Uani 1 1 d . . . C17 C 0.6062(9) 0.4652(9) 0.2028(8) 0.179(6) Uani 1 1 d . . . C18 C 0.6211(12) 0.4105(9) 0.1304(7) 0.191(6) Uani 1 1 d . . . H18A H 0.5982 0.4480 0.0875 0.230 Uiso 1 1 calc R . . H18B H 0.6919 0.3909 0.1233 0.230 Uiso 1 1 calc R . . C19 C 0.5539(10) 0.3266(8) 0.1452(4) 0.144(4) Uani 1 1 d . . . H19 H 0.5296 0.2931 0.1000 0.173 Uiso 1 1 calc R . . C20 C 0.6154(11) 0.2649(7) 0.1960(5) 0.162(5) Uani 1 1 d . . . H20A H 0.6858 0.2601 0.1791 0.195 Uiso 1 1 calc R . . H20B H 0.5866 0.1999 0.2001 0.195 Uiso 1 1 calc R . . C21 C 0.6078(11) 0.3211(8) 0.2721(5) 0.173(5) Uani 1 1 d . . . H21A H 0.5753 0.2814 0.3103 0.208 Uiso 1 1 calc R . . H21B H 0.6750 0.3410 0.2896 0.208 Uiso 1 1 calc R . . C22 C 0.4684(8) 0.3697(9) 0.1937(6) 0.151(4) Uani 1 1 d . . . C23 C 0.4003(12) 0.4387(17) 0.1602(7) 0.273(13) Uani 1 1 d . . . H23A H 0.4097 0.5013 0.1832 0.410 Uiso 1 1 calc R . . H23B H 0.3308 0.4177 0.1671 0.410 Uiso 1 1 calc R . . H23C H 0.4148 0.4435 0.1075 0.410 Uiso 1 1 calc R . . C24 C 0.3960(13) 0.2881(12) 0.2337(11) 0.241(9) Uani 1 1 d . . . H24A H 0.3254 0.3071 0.2293 0.362 Uiso 1 1 calc R . . H24B H 0.4139 0.2829 0.2857 0.362 Uiso 1 1 calc R . . H24C H 0.4059 0.2262 0.2096 0.362 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0704(7) 0.0649(7) 0.0590(6) 0.0041(6) -0.0082(5) -0.0051(5) S2 0.0561(5) 0.0481(5) 0.0595(6) -0.0047(5) -0.0001(4) 0.0008(4) O1 0.132(4) 0.080(3) 0.089(3) 0.023(2) -0.010(2) -0.029(2) O2 0.082(2) 0.084(3) 0.152(4) 0.017(3) -0.027(3) -0.012(2) O3 0.112(3) 0.101(3) 0.124(4) -0.040(3) 0.006(3) 0.015(3) O4 0.0578(16) 0.0591(17) 0.099(2) 0.001(2) -0.0046(16) -0.0031(14) O5 0.0637(18) 0.0594(17) 0.083(2) 0.0088(15) 0.0046(16) -0.0091(14) O6 0.094(3) 0.075(2) 0.094(3) -0.0171(19) 0.019(2) 0.016(2) O7 0.139(5) 0.183(6) 0.134(5) 0.003(4) -0.013(4) -0.063(5) O8 0.242(10) 0.166(7) 0.425(19) -0.125(10) 0.178(12) -0.106(7) N1 0.069(3) 0.070(2) 0.094(3) 0.004(2) -0.010(2) -0.010(2) N2 0.060(2) 0.064(2) 0.098(3) 0.012(2) 0.001(2) -0.0040(18) N3 0.065(2) 0.061(2) 0.134(4) 0.009(2) -0.017(3) -0.006(2) N4 0.054(2) 0.060(2) 0.100(3) 0.007(2) -0.002(2) 0.0051(17) N5 0.056(2) 0.066(2) 0.096(3) 0.007(2) -0.013(2) -0.0020(17) N6 0.060(2) 0.061(2) 0.097(3) 0.011(2) -0.005(2) 0.0038(18) C1 0.064(3) 0.051(2) 0.072(3) -0.006(2) 0.007(2) 0.0014(18) C2 0.069(3) 0.071(3) 0.163(6) 0.010(4) -0.008(4) -0.026(3) C3 0.048(2) 0.056(2) 0.064(3) 0.002(2) 0.0030(18) 0.0038(17) C4 0.067(3) 0.065(3) 0.196(8) 0.011(4) -0.022(4) 0.002(3) C5 0.107(4) 0.089(4) 0.074(3) 0.007(3) -0.018(3) 0.010(3) C6 0.089(3) 0.083(3) 0.062(3) -0.002(2) -0.011(2) -0.026(3) C7 0.170(8) 0.127(6) 0.094(5) 0.016(4) -0.004(5) -0.081(6) C8 0.278(14) 0.154(8) 0.092(5) -0.005(5) -0.048(7) -0.113(9) C9 0.333(19) 0.158(9) 0.067(4) -0.030(5) 0.001(7) -0.071(11) C10 0.183(10) 0.254(14) 0.140(8) -0.060(9) -0.022(8) 0.112(11) C11 0.200(10) 0.189(10) 0.095(5) 0.004(6) 0.006(6) 0.107(9) C12 0.138(7) 0.243(12) 0.069(4) 0.022(6) 0.001(4) -0.081(8) C13 0.207(12) 0.174(9) 0.135(7) 0.063(7) -0.022(8) 0.068(9) C14 0.248(15) 0.246(14) 0.132(8) 0.054(9) 0.032(9) -0.122(12) C15 0.101(4) 0.064(3) 0.079(3) 0.007(2) -0.020(3) 0.013(3) C16 0.088(3) 0.069(3) 0.062(3) -0.006(2) -0.010(2) 0.004(2) C17 0.160(9) 0.138(8) 0.238(13) -0.064(8) 0.102(9) -0.048(7) C18 0.257(14) 0.149(8) 0.168(10) -0.045(7) 0.128(10) -0.059(10) C19 0.197(10) 0.157(8) 0.078(4) -0.053(5) -0.013(6) 0.032(8) C20 0.273(13) 0.123(6) 0.091(5) -0.039(5) 0.006(7) 0.064(8) C21 0.268(13) 0.167(8) 0.084(4) -0.046(5) -0.025(6) 0.127(9) C22 0.139(7) 0.200(11) 0.115(6) -0.066(7) -0.024(6) 0.020(7) C23 0.185(12) 0.49(3) 0.146(9) -0.068(15) -0.098(9) 0.156(18) C24 0.225(14) 0.216(13) 0.282(18) -0.119(14) 0.084(13) -0.139(12) _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 1.409(4) . ? S1 O2 1.425(4) . ? S1 O3 1.482(5) . ? S1 C5 1.773(6) . ? S2 O4 1.445(3) . ? S2 O6 1.451(4) . ? S2 O5 1.460(3) . ? S2 C15 1.764(6) . ? O7 C7 1.174(10) . ? O8 C17 1.228(11) . ? N1 C1 1.325(7) . ? N2 C1 1.315(6) . ? N2 C2 1.429(7) . ? N3 C1 1.304(6) . ? N4 C3 1.317(5) . ? N4 C4 1.427(7) . ? N5 C3 1.331(6) . ? N6 C3 1.338(6) . ? C5 C6 1.470(9) . ? C6 C12 1.482(9) . ? C6 C7 1.554(9) . ? C6 C11 1.610(11) . ? C7 C8 1.455(12) . ? C8 C9 1.628(17) . ? C9 C12 1.430(16) . ? C9 C10 1.651(18) . ? C10 C11 1.472(13) . ? C12 C14 1.464(13) . ? C12 C13 1.610(15) . ? C15 C16 1.536(8) . ? C16 C17 1.436(12) . ? C16 C22 1.513(10) . ? C16 C21 1.553(10) . ? C17 C18 1.506(15) . ? C18 C19 1.471(15) . ? C19 C20 1.477(13) . ? C19 C22 1.531(14) . ? C20 C21 1.566(10) . ? C22 C23 1.429(18) . ? C22 C24 1.629(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 O1 S1 O2 112.7(3) . . ? O1 S1 O3 113.5(3) . . ? O2 S1 O3 107.9(3) . . ? O1 S1 C5 108.9(3) . . ? O2 S1 C5 110.4(3) . . ? O3 S1 C5 103.0(3) . . ? O4 S2 O6 112.0(2) . . ? O4 S2 O5 111.9(2) . . ? O6 S2 O5 112.7(2) . . ? O4 S2 C15 106.2(3) . . ? O6 S2 C15 103.9(3) . . ? O5 S2 C15 109.6(2) . . ? C1 N2 C2 125.2(5) . . ? C3 N4 C4 126.0(4) . . ? N3 C1 N2 121.4(5) . . ? N3 C1 N1 119.8(4) . . ? N2 C1 N1 118.8(5) . . ? N4 C3 N5 119.2(4) . . ? N4 C3 N6 120.9(4) . . ? N5 C3 N6 119.8(4) . . ? C6 C5 S1 119.7(4) . . ? C5 C6 C12 120.9(7) . . ? C5 C6 C7 111.6(6) . . ? C12 C6 C7 100.3(5) . . ? C5 C6 C11 119.4(6) . . ? C12 C6 C11 99.6(7) . . ? C7 C6 C11 101.8(8) . . ? O7 C7 C8 120.6(8) . . ? O7 C7 C6 130.5(8) . . ? C8 C7 C6 108.9(7) . . ? C7 C8 C9 99.6(6) . . ? C12 C9 C8 103.7(9) . . ? C12 C9 C10 96.5(9) . . ? C8 C9 C10 107.4(10) . . ? C11 C10 C9 102.3(8) . . ? C10 C11 C6 104.2(7) . . ? C9 C12 C14 114.8(11) . . ? C9 C12 C6 100.1(9) . . ? C14 C12 C6 115.9(8) . . ? C9 C12 C13 103.5(10) . . ? C14 C12 C13 108.8(11) . . ? C6 C12 C13 112.9(8) . . ? C16 C15 S2 119.7(4) . . ? C17 C16 C22 98.3(9) . . ? C17 C16 C15 112.7(6) . . ? C22 C16 C15 118.3(6) . . ? C17 C16 C21 102.6(9) . . ? C22 C16 C21 102.4(7) . . ? C15 C16 C21 119.5(5) . . ? O8 C17 C16 126.2(11) . . ? O8 C17 C18 123.6(11) . . ? C16 C17 C18 110.0(8) . . ? C19 C18 C17 99.2(7) . . ? C18 C19 C20 103.6(12) . . ? C18 C19 C22 103.5(8) . . ? C20 C19 C22 105.7(8) . . ? C19 C20 C21 102.5(7) . . ? C16 C21 C20 103.0(7) . . ? C23 C22 C16 115.4(11) . . ? C23 C22 C19 118.1(11) . . ? C16 C22 C19 94.5(7) . . ? C23 C22 C24 106.2(13) . . ? C16 C22 C24 108.4(10) . . ? C19 C22 C24 113.9(10) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.641 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.079 #===END data_compound_3b_h05njb5 _database_code_depnum_ccdc_archive 'CCDC 604285' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H25 N3 O4 S' _chemical_formula_weight 319.42 _chemical_absolute_structure syn 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.8940(1) _cell_length_b 17.4760(4) _cell_length_c 14.2100(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.180(1) _cell_angle_gamma 90.00 _cell_volume 1666.92(6) _cell_formula_units_Z 4 _cell_measurement_temperature 240(2) _cell_measurement_reflns_used 11498 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.952 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 240(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 KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16900 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 24.99 _reflns_number_total 5835 _reflns_number_gt 4392 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (otwinowski & Minor, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0822P)^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 SHELXL _refine_ls_extinction_coef 0.034(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(9) _refine_ls_number_reflns 5835 _refine_ls_number_parameters 387 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1313 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.15888(13) 0.14068(5) 0.51009(6) 0.0416(3) Uani 1 1 d . . . S2 S 0.83950(13) -0.23808(4) -0.01196(6) 0.0409(3) Uani 1 1 d . . . O1 O 1.2207(4) 0.19296(17) 0.4428(2) 0.0556(8) Uani 1 1 d . . . O2 O 0.9443(3) 0.14027(19) 0.50054(17) 0.0519(7) Uani 1 1 d . . . O3 O 1.2660(3) 0.15296(18) 0.60937(16) 0.0485(7) Uani 1 1 d . . . O4 O 1.0534(3) -0.24281(19) -0.00210(17) 0.0517(7) Uani 1 1 d . . . O5 O 0.7682(4) -0.29051(17) 0.0514(2) 0.0559(8) Uani 1 1 d . . . O6 O 0.7323(3) -0.2439(2) -0.11207(18) 0.0575(7) Uani 1 1 d . . . O7 O 1.1208(8) -0.0649(4) 0.1383(4) 0.170(2) Uani 1 1 d . . . O8 O 1.5723(4) -0.0142(2) 0.6022(3) 0.1018(11) Uani 1 1 d . . . N1 N 1.0138(4) 0.2144(2) 0.2452(2) 0.0563(10) Uani 1 1 d . . . H1A H 1.0678 0.2303 0.1991 0.068 Uiso 1 1 calc R . . H1B H 1.0885 0.2035 0.3017 0.068 Uiso 1 1 calc R . . N2 N 0.7417(4) 0.1824(2) 0.3029(2) 0.0514(10) Uani 1 1 d . . . H2 H 0.8246 0.1767 0.3586 0.062 Uiso 1 1 calc R . . N3 N 0.7051(5) 0.2229(2) 0.1447(2) 0.0534(10) Uani 1 1 d . . . H3A H 0.7589 0.2389 0.0986 0.064 Uiso 1 1 calc R . . H3B H 0.5764 0.2179 0.1345 0.064 Uiso 1 1 calc R . . N4 N 1.2541(4) -0.2825(2) 0.1955(2) 0.0481(9) Uani 1 1 d . . . H4 H 1.1704 -0.2723 0.1412 0.058 Uiso 1 1 calc R . . N5 N 0.9811(4) -0.3133(2) 0.2523(2) 0.0525(9) Uani 1 1 d . . . H5A H 0.9273 -0.3295 0.2984 0.063 Uiso 1 1 calc R . . H5B H 0.9060 -0.3009 0.1965 0.063 Uiso 1 1 calc R . . N6 N 1.2909(5) -0.3266(2) 0.3514(2) 0.0506(9) Uani 1 1 d . . . H6A H 1.2373 -0.3427 0.3975 0.061 Uiso 1 1 calc R . . H6B H 1.4198 -0.3229 0.3610 0.061 Uiso 1 1 calc R . . C1 C 0.8173(6) 0.2066(3) 0.2294(3) 0.0437(9) Uani 1 1 d . . . C2 C 0.5320(6) 0.1647(3) 0.2980(3) 0.0698(15) Uani 1 1 d . . . H2A H 0.5031 0.1745 0.3613 0.084 Uiso 1 1 calc R . . H2B H 0.4482 0.1990 0.2512 0.084 Uiso 1 1 calc R . . C3 C 0.4798(10) 0.0854(5) 0.2702(5) 0.123(3) Uani 1 1 d . . . H3C H 0.5094 0.0751 0.2079 0.184 Uiso 1 1 calc R . . H3D H 0.3389 0.0775 0.2660 0.184 Uiso 1 1 calc R . . H3E H 0.5567 0.0511 0.3183 0.184 Uiso 1 1 calc R . . C4 C 0.7875(7) -0.1470(3) 0.0297(3) 0.0596(12) Uani 1 1 d . . . H4A H 0.6425 -0.1427 0.0195 0.072 Uiso 1 1 calc R . . H4B H 0.8420 -0.1459 0.0997 0.072 Uiso 1 1 calc R . . C5 C 0.8608(6) -0.0758(2) -0.0124(3) 0.0546(11) Uani 1 1 d . . . C6 C 1.0213(8) -0.0342(4) 0.0648(5) 0.109(2) Uani 1 1 d . . . C7 C 1.0397(10) 0.0459(4) 0.0335(5) 0.117(2) Uani 1 1 d . . . H7A H 1.1710 0.0559 0.0205 0.140 Uiso 1 1 calc R . . H7B H 1.0139 0.0827 0.0812 0.140 Uiso 1 1 calc R . . C8 C 0.8749(7) 0.0469(3) -0.0592(4) 0.0749(14) Uani 1 1 d . . . H8 H 0.8244 0.0987 -0.0802 0.090 Uiso 1 1 calc R . . C9 C 0.9631(10) 0.0042(3) -0.1324(5) 0.111(2) Uani 1 1 d . . . H9A H 1.0989 0.0217 -0.1309 0.133 Uiso 1 1 calc R . . H9B H 0.8810 0.0105 -0.1979 0.133 Uiso 1 1 calc R . . C10 C 0.9620(10) -0.0782(3) -0.0988(5) 0.111(2) Uani 1 1 d . . . H10A H 1.0981 -0.0981 -0.0788 0.133 Uiso 1 1 calc R . . H10B H 0.8864 -0.1107 -0.1506 0.133 Uiso 1 1 calc R . . C11 C 0.7206(7) -0.0062(3) -0.0359(4) 0.0790(13) Uani 1 1 d . . . C12 C 0.6268(9) 0.0174(3) 0.0454(5) 0.114(2) Uani 1 1 d . . . H12A H 0.5566 0.0654 0.0292 0.171 Uiso 1 1 calc R . . H12B H 0.7297 0.0237 0.1041 0.171 Uiso 1 1 calc R . . H12C H 0.5337 -0.0217 0.0554 0.171 Uiso 1 1 calc R . . C13 C 0.5518(9) -0.0195(5) -0.1250(5) 0.142(3) Uani 1 1 d . . . H13A H 0.4903 0.0291 -0.1475 0.214 Uiso 1 1 calc R . . H13B H 0.4531 -0.0532 -0.1082 0.214 Uiso 1 1 calc R . . H13C H 0.6051 -0.0428 -0.1757 0.214 Uiso 1 1 calc R . . C14 C 1.1771(6) -0.3078(2) 0.2671(3) 0.0403(9) Uani 1 1 d . . . C15 C 1.4609(6) -0.2703(3) 0.1984(3) 0.0494(10) Uani 1 1 d . . . H15A H 1.4816 -0.2739 0.1325 0.059 Uiso 1 1 calc R . . H15B H 1.5388 -0.3111 0.2368 0.059 Uiso 1 1 calc R . . C16 C 1.5360(7) -0.1957(3) 0.2397(4) 0.0808(15) Uani 1 1 d . . . H16A H 1.4493 -0.1553 0.2075 0.121 Uiso 1 1 calc R . . H16B H 1.6697 -0.1876 0.2307 0.121 Uiso 1 1 calc R . . H16C H 1.5383 -0.1951 0.3082 0.121 Uiso 1 1 calc R . . C17 C 1.2257(7) 0.0495(2) 0.4747(3) 0.0612(13) Uani 1 1 d . . . H17A H 1.1411 0.0389 0.4107 0.073 Uiso 1 1 calc R . . H17B H 1.3629 0.0531 0.4667 0.073 Uiso 1 1 calc R . . C18 C 1.2150(6) -0.0197(2) 0.5379(3) 0.0513(9) Uani 1 1 d . . . C19 C 1.4177(7) -0.0510(3) 0.5871(3) 0.0701(12) Uani 1 1 d . . . C20 C 1.3896(8) -0.1330(3) 0.6137(4) 0.0896(15) Uani 1 1 d . . . H20A H 1.4320 -0.1410 0.6836 0.107 Uiso 1 1 calc R . . H20B H 1.4630 -0.1681 0.5807 0.107 Uiso 1 1 calc R . . C21 C 1.1665(8) -0.1431(3) 0.5783(4) 0.0771(14) Uani 1 1 d . . . H21 H 1.1222 -0.1970 0.5679 0.092 Uiso 1 1 calc R . . C22 C 1.0709(8) -0.0994(3) 0.6469(4) 0.0747(14) Uani 1 1 d . . . H22A H 1.1340 -0.1114 0.7143 0.090 Uiso 1 1 calc R . . H22B H 0.9281 -0.1104 0.6352 0.090 Uiso 1 1 calc R . . C23 C 1.1089(7) -0.0137(3) 0.6223(3) 0.0650(11) Uani 1 1 d . . . H23A H 0.9831 0.0143 0.6027 0.078 Uiso 1 1 calc R . . H23B H 1.1936 0.0121 0.6780 0.078 Uiso 1 1 calc R . . C24 C 1.1210(6) -0.0927(3) 0.4858(3) 0.0671(10) Uani 1 1 d . . . C25 C 1.2272(11) -0.1176(3) 0.4049(4) 0.120(2) Uani 1 1 d . . . H25A H 1.1797 -0.1678 0.3810 0.181 Uiso 1 1 calc R . . H25B H 1.3699 -0.1196 0.4311 0.181 Uiso 1 1 calc R . . H25C H 1.1980 -0.0809 0.3524 0.181 Uiso 1 1 calc R . . C26 C 0.8999(9) -0.0841(4) 0.4397(5) 0.117(2) Uani 1 1 d . . . H26A H 0.8303 -0.0674 0.4882 0.175 Uiso 1 1 calc R . . H26B H 0.8464 -0.1329 0.4134 0.175 Uiso 1 1 calc R . . H26C H 0.8821 -0.0465 0.3883 0.175 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0378(5) 0.0550(7) 0.0333(5) -0.0014(5) 0.0109(4) 0.0022(4) S2 0.0388(5) 0.0505(7) 0.0362(5) -0.0015(5) 0.0139(4) 0.0005(4) O1 0.0592(17) 0.0626(19) 0.0496(17) 0.0127(14) 0.0219(14) 0.0020(14) O2 0.0350(16) 0.079(2) 0.0429(14) 0.0048(15) 0.0115(13) 0.0074(14) O3 0.0399(13) 0.0701(19) 0.0344(13) -0.0055(14) 0.0064(11) -0.0016(14) O4 0.0407(17) 0.075(2) 0.0394(14) 0.0034(15) 0.0089(13) 0.0030(14) O5 0.0593(17) 0.0593(18) 0.0557(18) 0.0042(14) 0.0269(15) -0.0037(14) O6 0.0441(15) 0.085(2) 0.0422(14) -0.0096(16) 0.0067(12) -0.0007(16) O7 0.131(4) 0.177(5) 0.156(4) 0.071(4) -0.059(3) -0.043(3) O8 0.0506(17) 0.117(3) 0.134(3) 0.001(2) 0.0127(17) -0.0143(18) N1 0.041(2) 0.084(3) 0.048(2) 0.0060(19) 0.0175(18) -0.0007(18) N2 0.0386(18) 0.085(3) 0.0344(18) 0.0162(16) 0.0160(16) 0.0027(17) N3 0.0376(17) 0.080(3) 0.042(2) 0.0093(17) 0.0071(16) -0.0026(16) N4 0.0351(18) 0.066(2) 0.0431(19) 0.0012(16) 0.0090(16) 0.0032(15) N5 0.0328(19) 0.081(3) 0.044(2) 0.0121(17) 0.0102(16) 0.0004(17) N6 0.0453(18) 0.070(2) 0.0411(19) 0.0119(16) 0.0194(15) 0.0055(16) C1 0.039(2) 0.048(2) 0.045(2) -0.0017(18) 0.0126(19) 0.0042(18) C2 0.035(2) 0.120(4) 0.059(3) 0.031(3) 0.020(2) 0.009(2) C3 0.119(5) 0.162(6) 0.114(4) -0.083(4) 0.080(4) -0.086(4) C4 0.080(3) 0.058(3) 0.054(3) -0.010(2) 0.043(2) -0.005(2) C5 0.057(2) 0.046(2) 0.068(3) 0.0057(18) 0.029(2) 0.0053(19) C6 0.074(3) 0.116(5) 0.119(5) 0.033(4) -0.015(3) -0.016(3) C7 0.115(5) 0.097(4) 0.124(5) 0.024(4) -0.004(4) -0.026(3) C8 0.080(3) 0.056(3) 0.092(4) 0.017(3) 0.026(3) 0.013(2) C9 0.141(5) 0.089(5) 0.128(5) 0.033(4) 0.084(4) 0.016(4) C10 0.166(6) 0.063(3) 0.147(5) 0.021(3) 0.126(5) 0.010(3) C11 0.080(3) 0.070(3) 0.093(3) 0.006(2) 0.032(3) 0.014(2) C12 0.131(4) 0.084(4) 0.157(5) 0.014(4) 0.094(4) 0.038(4) C13 0.093(4) 0.211(9) 0.099(4) 0.020(5) -0.029(4) -0.014(5) C14 0.041(2) 0.050(3) 0.0341(19) -0.0019(17) 0.0155(18) 0.0020(18) C15 0.041(2) 0.069(3) 0.039(2) -0.0028(19) 0.0111(18) -0.0034(19) C16 0.057(3) 0.090(4) 0.102(4) 0.005(3) 0.033(3) -0.004(3) C17 0.084(3) 0.052(3) 0.060(3) -0.003(2) 0.040(3) 0.002(2) C18 0.052(2) 0.058(2) 0.0462(19) -0.0041(17) 0.0143(17) 0.0010(18) C19 0.056(3) 0.079(3) 0.075(3) -0.006(2) 0.014(2) 0.001(2) C20 0.085(3) 0.068(3) 0.118(4) 0.013(3) 0.029(3) 0.019(3) C21 0.093(3) 0.047(3) 0.090(3) 0.006(2) 0.019(3) -0.009(2) C22 0.080(3) 0.065(3) 0.080(3) 0.017(3) 0.022(3) -0.011(3) C23 0.078(3) 0.066(3) 0.059(2) 0.010(2) 0.033(2) 0.003(2) C24 0.075(3) 0.066(3) 0.058(2) -0.013(2) 0.009(2) -0.011(2) C25 0.194(7) 0.080(4) 0.099(4) -0.046(3) 0.057(4) -0.001(4) C26 0.088(4) 0.147(6) 0.093(4) 0.004(4) -0.026(3) -0.036(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 O3 1.451(2) . ? S1 O2 1.454(2) . ? S1 O1 1.455(3) . ? S1 C17 1.763(4) . ? S2 O5 1.447(3) . ? S2 O6 1.449(3) . ? S2 O4 1.451(2) . ? S2 C4 1.762(4) . ? O7 C6 1.234(7) . ? O8 C19 1.221(5) . ? N1 C1 1.328(4) . ? N2 C1 1.337(5) . ? N2 C2 1.465(5) . ? N3 C1 1.305(5) . ? N4 C14 1.325(5) . ? N4 C15 1.433(5) . ? N5 C14 1.323(4) . ? N6 C14 1.315(5) . ? C2 C3 1.463(9) . ? C4 C5 1.517(6) . ? C5 C11 1.542(6) . ? C5 C10 1.546(6) . ? C5 C6 1.549(7) . ? C6 C7 1.482(8) . ? C7 C8 1.531(7) . ? C8 C11 1.505(7) . ? C8 C9 1.515(7) . ? C9 C10 1.518(8) . ? C11 C12 1.505(7) . ? C11 C13 1.529(7) . ? C15 C16 1.475(6) . ? C17 C18 1.519(6) . ? C18 C19 1.515(6) . ? C18 C24 1.542(6) . ? C18 C23 1.545(5) . ? C19 C20 1.506(7) . ? C20 C21 1.516(7) . ? C21 C22 1.503(7) . ? C21 C24 1.554(7) . ? C22 C23 1.572(6) . ? C24 C26 1.523(7) . ? C24 C25 1.558(6) . ? 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 O3 S1 O2 111.87(15) . . ? O3 S1 O1 112.69(18) . . ? O2 S1 O1 112.70(16) . . ? O3 S1 C17 107.6(2) . . ? O2 S1 C17 107.2(2) . . ? O1 S1 C17 104.20(18) . . ? O5 S2 O6 113.36(18) . . ? O5 S2 O4 112.67(17) . . ? O6 S2 O4 111.72(15) . . ? O5 S2 C4 103.83(17) . . ? O6 S2 C4 107.2(2) . . ? O4 S2 C4 107.4(2) . . ? C1 N2 C2 125.9(3) . . ? C14 N4 C15 126.7(4) . . ? N3 C1 N1 120.1(4) . . ? N3 C1 N2 122.3(4) . . ? N1 C1 N2 117.6(4) . . ? C3 C2 N2 113.1(5) . . ? C5 C4 S2 119.8(3) . . ? C4 C5 C11 119.0(3) . . ? C4 C5 C10 122.8(4) . . ? C11 C5 C10 102.9(4) . . ? C4 C5 C6 110.8(4) . . ? C11 C5 C6 95.5(4) . . ? C10 C5 C6 101.3(4) . . ? O7 C6 C7 126.5(6) . . ? O7 C6 C5 124.3(6) . . ? C7 C6 C5 109.1(5) . . ? C6 C7 C8 99.9(5) . . ? C11 C8 C9 105.1(4) . . ? C11 C8 C7 103.1(4) . . ? C9 C8 C7 104.5(5) . . ? C8 C9 C10 102.7(4) . . ? C9 C10 C5 105.0(4) . . ? C8 C11 C12 116.7(5) . . ? C8 C11 C13 110.8(5) . . ? C12 C11 C13 107.4(5) . . ? C8 C11 C5 95.4(3) . . ? C12 C11 C5 114.0(4) . . ? C13 C11 C5 112.4(5) . . ? N6 C14 N5 120.1(4) . . ? N6 C14 N4 121.5(4) . . ? N5 C14 N4 118.4(4) . . ? N4 C15 C16 113.5(4) . . ? C18 C17 S1 120.0(3) . . ? C19 C18 C17 113.4(4) . . ? C19 C18 C24 99.5(3) . . ? C17 C18 C24 116.6(3) . . ? C19 C18 C23 102.5(3) . . ? C17 C18 C23 120.0(4) . . ? C24 C18 C23 102.0(3) . . ? O8 C19 C20 127.9(5) . . ? O8 C19 C18 124.6(4) . . ? C20 C19 C18 107.5(4) . . ? C19 C20 C21 101.9(4) . . ? C22 C21 C20 106.7(4) . . ? C22 C21 C24 103.1(4) . . ? C20 C21 C24 102.0(4) . . ? C21 C22 C23 102.7(4) . . ? C18 C23 C22 103.9(4) . . ? C26 C24 C18 113.2(4) . . ? C26 C24 C21 114.1(4) . . ? C18 C24 C21 94.6(3) . . ? C26 C24 C25 107.7(5) . . ? C18 C24 C25 111.6(4) . . ? C21 C24 C25 115.4(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.330 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.091 #===END data_compound_3c_bath113a _database_code_depnum_ccdc_archive 'CCDC 604286' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H25 N3 O4 S' _chemical_formula_weight 319.42 _chemical_absolute_structure syn 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.8207(16) _cell_length_b 13.254(2) _cell_length_c 11.8837(18) _cell_angle_alpha 90.00 _cell_angle_beta 103.423(2) _cell_angle_gamma 90.00 _cell_volume 1657.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 240(2) _cell_measurement_reflns_used 4652 _cell_measurement_theta_min 6.76 _cell_measurement_theta_max 49.46 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.015 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9745 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.67780 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14198 _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_sigmaI/netI 0.1333 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6590 _reflns_number_gt 5835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT V7.06a' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.1418P)^2^+0.8752P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(13) _refine_ls_number_reflns 6590 _refine_ls_number_parameters 379 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0946 _refine_ls_R_factor_gt 0.0888 _refine_ls_wR_factor_ref 0.2469 _refine_ls_wR_factor_gt 0.2392 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.88419(9) -0.02653(7) 0.65923(8) 0.0338(3) Uani 1 1 d . . . S2 S 0.62293(9) 0.41514(7) 0.83447(8) 0.0361(3) Uani 1 1 d . . . O1 O 0.8556(4) 0.0673(3) 0.7100(3) 0.0569(10) Uani 1 1 d . . . O2 O 0.7979(4) -0.0450(4) 0.5518(4) 0.0730(14) Uani 1 1 d . . . O3 O 0.9051(4) -0.1098(4) 0.7383(4) 0.0650(13) Uani 1 1 d . . . O4 O 0.7233(5) 0.4322(4) 0.9350(4) 0.0927(18) Uani 1 1 d . . . O5 O 0.6500(3) 0.3293(3) 0.7689(3) 0.0555(10) Uani 1 1 d . . . O6 O 0.5900(4) 0.5052(4) 0.7673(4) 0.0693(13) Uani 1 1 d . . . O7 O 1.2967(6) 0.0364(7) 0.6516(8) 0.135(3) Uani 1 1 d . . . O8 O 0.5096(11) 0.3187(6) 1.1225(9) 0.167(4) Uani 1 1 d . . . N1 N 0.6024(4) 0.1496(3) 0.6309(3) 0.0403(9) Uani 1 1 d . . . H1B H 0.5839 0.1943 0.6780 0.048 Uiso 1 1 calc R . . H1A H 0.6668 0.1094 0.6541 0.048 Uiso 1 1 calc R . . N2 N 0.5652(4) 0.0743(3) 0.4552(3) 0.0457(10) Uani 1 1 d . . . H2B H 0.5217 0.0684 0.3841 0.055 Uiso 1 1 calc R . . H2A H 0.6302 0.0353 0.4811 0.055 Uiso 1 1 calc R . . N3 N 0.4353(4) 0.2033(3) 0.4887(4) 0.0452(10) Uani 1 1 d . . . N4 N 0.9323(4) 0.3094(4) 1.0462(3) 0.0493(10) Uani 1 1 d . . . H4A H 0.8685 0.3498 1.0213 0.059 Uiso 1 1 calc R . . H4B H 0.9764 0.3139 1.1172 0.059 Uiso 1 1 calc R . . N5 N 0.8941(4) 0.2344(3) 0.8667(3) 0.0415(9) Uani 1 1 d . . . H5A H 0.8303 0.2750 0.8422 0.050 Uiso 1 1 calc R . . H5B H 0.9135 0.1895 0.8203 0.050 Uiso 1 1 calc R . . N6 N 1.0597(4) 0.1772(3) 1.0131(3) 0.0435(10) Uani 1 1 d . . . C1 C 0.5325(4) 0.1427(3) 0.5239(4) 0.0355(9) Uani 1 1 d . . . C2 C 0.3657(7) 0.2040(5) 0.3667(5) 0.075(2) Uani 1 1 d . . . H2C H 0.2970 0.2527 0.3562 0.113 Uiso 1 1 calc R . . H2D H 0.3310 0.1374 0.3451 0.113 Uiso 1 1 calc R . . H2E H 0.4231 0.2224 0.3184 0.113 Uiso 1 1 calc R . . C3 C 0.3908(5) 0.2682(5) 0.5701(5) 0.0598(15) Uani 1 1 d . . . H3A H 0.3185 0.3073 0.5290 0.090 Uiso 1 1 calc R . . H3B H 0.4585 0.3136 0.6069 0.090 Uiso 1 1 calc R . . H3C H 0.3657 0.2271 0.6286 0.090 Uiso 1 1 calc R . . C4 C 0.9623(4) 0.2411(4) 0.9760(4) 0.0358(10) Uani 1 1 d . . . C5 C 1.1008(6) 0.1090(6) 0.9328(5) 0.072(2) Uani 1 1 d . . . H5C H 1.1719 0.0689 0.9743 0.108 Uiso 1 1 calc R . . H5D H 1.1268 0.1479 0.8731 0.108 Uiso 1 1 calc R . . H5E H 1.0312 0.0648 0.8975 0.108 Uiso 1 1 calc R . . C6 C 1.1300(7) 0.1739(6) 1.1324(4) 0.0666(18) Uani 1 1 d . . . H6A H 1.1965 0.1235 1.1411 0.100 Uiso 1 1 calc R . . H6B H 1.0729 0.1566 1.1814 0.100 Uiso 1 1 calc R . . H6C H 1.1677 0.2395 1.1547 0.100 Uiso 1 1 calc R . . C7 C 1.0352(5) 0.0017(4) 0.6283(5) 0.0535(13) Uani 1 1 d . . . H7A H 1.0204 0.0547 0.5692 0.064 Uiso 1 1 calc R . . H7B H 1.0883 0.0315 0.6985 0.064 Uiso 1 1 calc R . . C8 C 1.1131(5) -0.0781(4) 0.5887(4) 0.0513(11) Uani 1 1 d . . . C9 C 1.2526(8) -0.0368(7) 0.5976(10) 0.101(3) Uani 1 1 d . . . C10 C 1.3138(9) -0.1052(9) 0.5282(10) 0.115(3) Uani 1 1 d . . . H10A H 1.3357 -0.0693 0.4634 0.138 Uiso 1 1 calc R . . H10B H 1.3906 -0.1360 0.5759 0.138 Uiso 1 1 calc R . . C11 C 1.2159(8) -0.1801(7) 0.4877(7) 0.084(2) Uani 1 1 d . . . H11 H 1.2284 -0.2188 0.4199 0.101 Uiso 1 1 calc R . . C12 C 1.2059(11) -0.2467(7) 0.5897(10) 0.117(4) Uani 1 1 d . . . H12A H 1.1507 -0.3049 0.5641 0.141 Uiso 1 1 calc R . . H12B H 1.2898 -0.2707 0.6312 0.141 Uiso 1 1 calc R . . C13 C 1.1484(7) -0.1768(7) 0.6650(6) 0.084(2) Uani 1 1 d . . . H13A H 1.2099 -0.1616 0.7376 0.101 Uiso 1 1 calc R . . H13B H 1.0725 -0.2070 0.6829 0.101 Uiso 1 1 calc R . . C14 C 1.0867(7) -0.1227(7) 0.4648(6) 0.081(2) Uani 1 1 d . . . C15 C 1.0738(10) -0.0394(11) 0.3777(7) 0.124(4) Uani 1 1 d . . . H15A H 1.1483 0.0035 0.3965 0.186 Uiso 1 1 calc R . . H15B H 0.9987 0.0002 0.3789 0.186 Uiso 1 1 calc R . . H15C H 1.0659 -0.0680 0.3012 0.186 Uiso 1 1 calc R . . C16 C 0.9710(9) -0.1902(9) 0.4371(11) 0.133(5) Uani 1 1 d . . . H16A H 0.9788 -0.2420 0.4959 0.200 Uiso 1 1 calc R . . H16B H 0.9645 -0.2215 0.3622 0.200 Uiso 1 1 calc R . . H16C H 0.8955 -0.1502 0.4354 0.200 Uiso 1 1 calc R . . C17 C 0.4843(8) 0.3808(5) 0.8799(7) 0.088(3) Uani 1 1 d . . . H17A H 0.4138 0.3781 0.8113 0.106 Uiso 1 1 calc R . . H17B H 0.4966 0.3122 0.9115 0.106 Uiso 1 1 calc R . . C18 C 0.4442(7) 0.4471(5) 0.9688(7) 0.0750(19) Uani 1 1 d . . . C19 C 0.4574(9) 0.3938(6) 1.0869(8) 0.090(2) Uani 1 1 d . . . C20 C 0.3752(13) 0.4501(8) 1.1496(10) 0.128(4) Uani 1 1 d . . . H20A H 0.4251 0.4795 1.2216 0.153 Uiso 1 1 calc R . . H20B H 0.3089 0.4067 1.1672 0.153 Uiso 1 1 calc R . . C21 C 0.3172(10) 0.5340(6) 1.0599(9) 0.107(3) Uani 1 1 d . . . H21 H 0.2363 0.5631 1.0702 0.129 Uiso 1 1 calc R . . C22 C 0.4203(12) 0.6078(7) 1.0647(10) 0.123(4) Uani 1 1 d . . . H22A H 0.3885 0.6686 1.0202 0.147 Uiso 1 1 calc R . . H22B H 0.4586 0.6272 1.1447 0.147 Uiso 1 1 calc R . . C23 C 0.5131(13) 0.5544(8) 1.0127(10) 0.125(4) Uani 1 1 d . . . H23A H 0.5930 0.5435 1.0701 0.150 Uiso 1 1 calc R . . H23B H 0.5307 0.5928 0.9477 0.150 Uiso 1 1 calc R . . C24 C 0.3075(11) 0.4777(9) 0.9456(12) 0.125(4) Uani 1 1 d . . . C25 C 0.2262(11) 0.3833(11) 0.9216(13) 0.142(5) Uani 1 1 d . . . H25A H 0.1372 0.4018 0.9062 0.213 Uiso 1 1 calc R . . H25B H 0.2465 0.3391 0.9885 0.213 Uiso 1 1 calc R . . H25C H 0.2431 0.3486 0.8549 0.213 Uiso 1 1 calc R . . C26 C 0.2670(16) 0.5558(16) 0.8438(12) 0.209(9) Uani 1 1 d . . . H26A H 0.3205 0.6152 0.8601 0.313 Uiso 1 1 calc R . . H26B H 0.1790 0.5750 0.8365 0.313 Uiso 1 1 calc R . . H26C H 0.2766 0.5253 0.7721 0.313 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0358(5) 0.0332(6) 0.0325(5) 0.0003(4) 0.0082(4) 0.0092(4) S2 0.0359(5) 0.0384(6) 0.0319(5) -0.0014(4) 0.0038(4) 0.0042(4) O1 0.056(2) 0.055(2) 0.0520(19) -0.0241(17) -0.0037(15) 0.0104(18) O2 0.061(2) 0.077(3) 0.068(2) -0.030(2) -0.012(2) 0.020(2) O3 0.060(2) 0.074(3) 0.069(2) 0.036(2) 0.031(2) 0.025(2) O4 0.082(3) 0.072(3) 0.089(3) -0.033(3) -0.049(2) 0.030(3) O5 0.0441(18) 0.061(2) 0.065(2) -0.0245(19) 0.0200(16) 0.0044(17) O6 0.080(3) 0.067(3) 0.066(2) 0.035(2) 0.027(2) 0.023(2) O7 0.062(3) 0.145(7) 0.204(7) -0.044(6) 0.040(4) -0.027(4) O8 0.239(11) 0.085(5) 0.193(9) 0.034(6) 0.084(8) 0.031(6) N1 0.042(2) 0.038(2) 0.0350(18) -0.0023(16) -0.0022(16) 0.0072(17) N2 0.050(2) 0.038(2) 0.044(2) -0.0107(17) 0.0007(18) 0.0095(19) N3 0.040(2) 0.042(2) 0.044(2) -0.0091(18) -0.0093(17) 0.0072(17) N4 0.049(2) 0.052(3) 0.040(2) -0.0130(19) -0.0041(17) 0.009(2) N5 0.0397(19) 0.044(2) 0.0328(18) -0.0060(16) -0.0071(15) 0.0126(17) N6 0.047(2) 0.043(2) 0.0322(18) -0.0065(16) -0.0079(16) 0.0146(18) C1 0.037(2) 0.029(2) 0.035(2) 0.0017(17) -0.0020(17) -0.0012(17) C2 0.084(4) 0.059(4) 0.055(3) -0.007(3) -0.039(3) 0.022(3) C3 0.047(3) 0.070(4) 0.053(3) -0.018(3) -0.009(2) 0.025(3) C4 0.036(2) 0.035(2) 0.033(2) -0.0013(18) 0.0013(17) -0.0003(18) C5 0.065(4) 0.081(4) 0.058(3) -0.025(3) -0.010(3) 0.039(3) C6 0.082(4) 0.068(4) 0.036(3) -0.010(3) -0.015(3) 0.021(3) C7 0.052(3) 0.036(3) 0.078(3) -0.006(2) 0.024(3) -0.002(2) C8 0.050(2) 0.051(3) 0.061(3) -0.007(2) 0.029(2) 0.005(2) C9 0.073(4) 0.082(5) 0.162(8) -0.040(6) 0.054(5) -0.007(4) C10 0.090(5) 0.129(8) 0.147(8) -0.015(7) 0.067(6) 0.012(6) C11 0.089(5) 0.093(5) 0.086(4) 0.005(4) 0.052(4) 0.033(4) C12 0.138(8) 0.076(5) 0.162(9) 0.004(5) 0.084(7) 0.041(5) C13 0.082(4) 0.107(6) 0.074(4) 0.025(4) 0.038(3) 0.032(4) C14 0.078(4) 0.096(5) 0.076(4) -0.022(4) 0.030(3) 0.014(4) C15 0.123(7) 0.182(12) 0.079(5) 0.048(6) 0.050(5) 0.063(8) C16 0.088(6) 0.125(8) 0.181(10) -0.098(8) 0.020(6) 0.003(5) C17 0.114(6) 0.060(4) 0.122(6) -0.033(4) 0.090(5) -0.022(4) C18 0.102(5) 0.045(3) 0.101(5) -0.017(3) 0.071(4) -0.002(3) C19 0.120(6) 0.057(4) 0.105(6) 0.005(4) 0.050(5) 0.005(4) C20 0.201(12) 0.083(6) 0.134(8) 0.013(5) 0.109(9) 0.007(7) C21 0.137(7) 0.070(5) 0.152(8) -0.008(5) 0.110(7) 0.018(5) C22 0.198(11) 0.057(4) 0.147(8) -0.032(5) 0.110(8) -0.013(5) C23 0.192(11) 0.096(6) 0.125(7) -0.042(6) 0.114(8) -0.046(7) C24 0.128(8) 0.099(7) 0.173(10) -0.025(7) 0.084(8) -0.023(6) C25 0.101(7) 0.163(14) 0.179(12) 0.013(10) 0.070(8) -0.002(8) C26 0.226(17) 0.24(2) 0.134(11) 0.095(14) -0.019(10) 0.016(16) _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 1.417(4) . ? S1 O3 1.433(4) . ? S1 O1 1.447(4) . ? S1 C7 1.796(5) . ? S2 O4 1.434(4) . ? S2 O6 1.434(4) . ? S2 O5 1.447(4) . ? S2 C17 1.768(6) . ? O7 C9 1.199(11) . ? O8 C19 1.174(12) . ? N1 C1 1.322(5) . ? N2 C1 1.322(6) . ? N3 C1 1.312(6) . ? N3 C3 1.457(7) . ? N3 C2 1.471(6) . ? N4 C4 1.321(6) . ? N5 C4 1.340(5) . ? N6 C4 1.344(6) . ? N6 C6 1.446(6) . ? N6 C5 1.457(6) . ? C7 C8 1.495(7) . ? C8 C14 1.550(8) . ? C8 C9 1.585(9) . ? C8 C13 1.588(9) . ? C9 C10 1.481(11) . ? C10 C11 1.451(14) . ? C11 C12 1.522(12) . ? C11 C14 1.559(10) . ? C12 C13 1.518(10) . ? C14 C15 1.498(14) . ? C14 C16 1.511(13) . ? C17 C18 1.513(7) . ? C18 C24 1.496(14) . ? C18 C19 1.548(11) . ? C18 C23 1.635(12) . ? C19 C20 1.487(12) . ? C20 C21 1.567(15) . ? C21 C22 1.475(14) . ? C21 C24 1.532(14) . ? C22 C23 1.476(13) . ? C24 C25 1.518(17) . ? C24 C26 1.575(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 O2 S1 O3 115.4(3) . . ? O2 S1 O1 111.3(2) . . ? O3 S1 O1 113.9(2) . . ? O2 S1 C7 107.0(3) . . ? O3 S1 C7 106.4(2) . . ? O1 S1 C7 101.5(2) . . ? O4 S2 O6 112.0(3) . . ? O4 S2 O5 111.4(3) . . ? O6 S2 O5 114.2(2) . . ? O4 S2 C17 108.5(4) . . ? O6 S2 C17 105.4(4) . . ? O5 S2 C17 104.7(3) . . ? C1 N3 C3 120.9(4) . . ? C1 N3 C2 120.5(4) . . ? C3 N3 C2 118.5(4) . . ? C4 N6 C6 122.3(4) . . ? C4 N6 C5 120.8(4) . . ? C6 N6 C5 116.9(4) . . ? N3 C1 N2 122.1(4) . . ? N3 C1 N1 120.1(4) . . ? N2 C1 N1 117.8(4) . . ? N4 C4 N5 119.7(4) . . ? N4 C4 N6 120.9(4) . . ? N5 C4 N6 119.3(4) . . ? C8 C7 S1 121.6(4) . . ? C7 C8 C14 125.2(5) . . ? C7 C8 C9 109.4(5) . . ? C14 C8 C9 99.1(5) . . ? C7 C8 C13 118.8(4) . . ? C14 C8 C13 101.2(5) . . ? C9 C8 C13 98.5(6) . . ? O7 C9 C10 128.2(8) . . ? O7 C9 C8 124.8(7) . . ? C10 C9 C8 107.0(7) . . ? C11 C10 C9 102.6(7) . . ? C10 C11 C12 108.3(9) . . ? C10 C11 C14 106.2(7) . . ? C12 C11 C14 101.3(6) . . ? C13 C12 C11 103.3(6) . . ? C12 C13 C8 104.0(5) . . ? C15 C14 C16 110.2(9) . . ? C15 C14 C8 110.0(8) . . ? C16 C14 C8 113.2(7) . . ? C15 C14 C11 114.6(6) . . ? C16 C14 C11 114.4(8) . . ? C8 C14 C11 93.5(6) . . ? C18 C17 S2 117.7(5) . . ? C24 C18 C17 117.4(8) . . ? C24 C18 C19 99.8(7) . . ? C17 C18 C19 112.7(6) . . ? C24 C18 C23 100.4(7) . . ? C17 C18 C23 123.0(5) . . ? C19 C18 C23 99.7(7) . . ? O8 C19 C20 122.6(10) . . ? O8 C19 C18 130.5(9) . . ? C20 C19 C18 106.6(7) . . ? C19 C20 C21 101.9(6) . . ? C22 C21 C24 104.6(6) . . ? C22 C21 C20 105.4(10) . . ? C24 C21 C20 101.1(8) . . ? C23 C22 C21 104.4(7) . . ? C22 C23 C18 104.3(8) . . ? C18 C24 C25 108.4(10) . . ? C18 C24 C21 96.2(9) . . ? C25 C24 C21 119.0(9) . . ? C18 C24 C26 114.0(9) . . ? C25 C24 C26 110.6(13) . . ? C21 C24 C26 108.1(11) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.716 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.080 #===END data_compound_4_bath43 _database_code_depnum_ccdc_archive 'CCDC 604287' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H13 N3 O3 S' _chemical_formula_weight 183.23 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.4309(5) _cell_length_b 7.9829(6) _cell_length_c 16.2140(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.057(2) _cell_angle_gamma 90.00 _cell_volume 831.85(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.357 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68670 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7977 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 29.27 _reflns_number_total 2335 _reflns_number_gt 2108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0750P)^2^+0.3444P] 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 2335 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.57878(5) 0.14905(4) 0.62848(2) 0.01732(14) Uani 1 1 d . . . O1 O 0.76983(17) 0.07088(13) 0.59974(7) 0.0233(2) Uani 1 1 d . . . O2 O 0.50111(18) 0.27563(14) 0.56923(8) 0.0291(3) Uani 1 1 d . . . O3 O 0.59924(19) 0.21174(15) 0.71206(7) 0.0298(3) Uani 1 1 d . . . N1 N 1.00577(19) 0.22478(15) 0.46707(8) 0.0207(3) Uani 1 1 d . . . H1B H 0.9363 0.1807 0.5075 0.025 Uiso 1 1 calc R . . H1A H 1.1250 0.1807 0.4533 0.025 Uiso 1 1 calc R . . N2 N 0.75104(19) 0.42462(15) 0.44984(8) 0.0202(3) Uani 1 1 d . . . H2B H 0.6997 0.5139 0.4247 0.024 Uiso 1 1 calc R . . H2A H 0.6841 0.3786 0.4904 0.024 Uiso 1 1 calc R . . N3 N 1.03403(19) 0.42657(15) 0.36533(8) 0.0201(3) Uani 1 1 d . . . C1 C 0.9300(2) 0.35918(15) 0.42650(9) 0.0168(3) Uani 1 1 d . . . C2 C 0.9404(3) 0.5588(2) 0.31337(10) 0.0261(3) Uani 1 1 d . . . H2E H 0.7963 0.5289 0.2983 0.039 Uiso 1 1 calc R . . H2D H 1.0198 0.5711 0.2632 0.039 Uiso 1 1 calc R . . H2C H 0.9427 0.6648 0.3439 0.039 Uiso 1 1 calc R . . C3 C 1.2423(2) 0.36846(19) 0.34606(10) 0.0237(3) Uani 1 1 d . . . H3A H 1.3197 0.3401 0.3973 0.036 Uiso 1 1 calc R . . H3B H 1.3157 0.4573 0.3172 0.036 Uiso 1 1 calc R . . H3C H 1.2311 0.2690 0.3107 0.036 Uiso 1 1 calc R . . C4 C 0.3876(2) -0.00936(19) 0.62711(10) 0.0248(3) Uani 1 1 d . . . H4A H 0.4230 -0.0927 0.6697 0.037 Uiso 1 1 calc R . . H4B H 0.3816 -0.0637 0.5729 0.037 Uiso 1 1 calc R . . H4C H 0.2518 0.0402 0.6380 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0216(2) 0.00801(18) 0.0227(2) 0.00041(10) 0.00539(13) 0.00096(10) O1 0.0252(5) 0.0144(5) 0.0307(6) 0.0017(4) 0.0086(4) 0.0054(4) O2 0.0301(6) 0.0179(5) 0.0399(7) 0.0140(5) 0.0105(5) 0.0078(4) O3 0.0366(6) 0.0249(6) 0.0282(6) -0.0098(5) 0.0070(5) -0.0060(5) N1 0.0212(6) 0.0123(5) 0.0288(6) 0.0034(4) 0.0044(5) 0.0027(4) N2 0.0215(6) 0.0121(5) 0.0273(6) 0.0031(4) 0.0052(5) 0.0027(4) N3 0.0209(6) 0.0153(5) 0.0243(6) 0.0031(4) 0.0039(4) 0.0023(4) C1 0.0189(6) 0.0097(6) 0.0216(6) -0.0027(4) 0.0001(5) -0.0013(4) C2 0.0284(7) 0.0212(7) 0.0287(8) 0.0079(6) 0.0021(6) 0.0012(6) C3 0.0214(7) 0.0183(6) 0.0318(8) -0.0019(5) 0.0076(6) 0.0006(5) C4 0.0283(7) 0.0156(6) 0.0307(8) -0.0005(5) 0.0040(6) -0.0049(5) _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 O3 1.4461(12) . ? S1 O1 1.4687(11) . ? S1 O2 1.4694(11) . ? S1 C4 1.7635(15) . ? N1 C1 1.3409(17) . ? N2 C1 1.3312(18) . ? N3 C1 1.3298(19) . ? N3 C3 1.4619(18) . ? N3 C2 1.4661(19) . ? 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 O3 S1 O1 113.29(7) . . ? O3 S1 O2 113.08(7) . . ? O1 S1 O2 110.69(7) . . ? O3 S1 C4 107.45(7) . . ? O1 S1 C4 106.39(7) . . ? O2 S1 C4 105.33(8) . . ? C1 N3 C3 121.35(13) . . ? C1 N3 C2 120.85(12) . . ? C3 N3 C2 117.78(12) . . ? N3 C1 N2 121.09(13) . . ? N3 C1 N1 120.39(13) . . ? N2 C1 N1 118.50(13) . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 29.27 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.773 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.112 #===END data_compound_5_bath44 _database_code_depnum_ccdc_archive 'CCDC 604288' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 N3 O3 S' _chemical_formula_weight 245.30 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 Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 10.6084(4) _cell_length_b 11.3449(5) _cell_length_c 10.0582(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1210.52(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68670 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8195 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 29.37 _reflns_number_total 3343 _reflns_number_gt 3197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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 [1.00000+0.00000exp(0.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.1255*P+(0.0616P)^2^+0.0000sin\q/\l] where P = 0.00000Fo^2^ + 1.00000Fc^2^ ; _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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.54(7) _refine_ls_number_reflns 3343 _refine_ls_number_parameters 148 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.47560(3) 0.20860(3) 0.40478(5) 0.02201(10) Uani 1 1 d . . . O1 O 0.39645(12) 0.23775(13) 0.51813(11) 0.0342(3) Uani 1 1 d . . . N1 N 0.13379(13) 0.15217(14) 0.51190(13) 0.0270(3) Uani 1 1 d . . . H1A H 0.2163 0.1591 0.5076 0.032 Uiso 1 1 calc R . . H1B H 0.0960 0.1493 0.5897 0.032 Uiso 1 1 calc R . . C1 C 0.06597(12) 0.14605(11) 0.40055(17) 0.0223(2) Uani 1 1 d . . . O2 O 0.39946(11) 0.17433(14) 0.29058(11) 0.0333(3) Uani 1 1 d . . . N2 N 0.12660(14) 0.15077(14) 0.28459(14) 0.0291(3) Uani 1 1 d . . . H2A H 0.2092 0.1577 0.2830 0.035 Uiso 1 1 calc R . . H2B H 0.0840 0.1469 0.2096 0.035 Uiso 1 1 calc R . . C2 C -0.13227(18) 0.12755(19) 0.28288(18) 0.0329(4) Uani 1 1 d . . . H2C H -0.1277 0.2031 0.2358 0.049 Uiso 1 1 calc R . . H2D H -0.2204 0.1098 0.3042 0.049 Uiso 1 1 calc R . . H2E H -0.0979 0.0650 0.2263 0.049 Uiso 1 1 calc R . . O3 O 0.57328(12) 0.12464(12) 0.43729(16) 0.0416(4) Uani 1 1 d . . . N3 N -0.05909(10) 0.13469(10) 0.40553(15) 0.0238(2) Uani 1 1 d . . . C3 C -0.12242(17) 0.11990(19) 0.53323(17) 0.0327(4) Uani 1 1 d . . . H3A H -0.0869 0.0516 0.5796 0.049 Uiso 1 1 calc R . . H3B H -0.2127 0.1074 0.5185 0.049 Uiso 1 1 calc R . . H3C H -0.1101 0.1908 0.5874 0.049 Uiso 1 1 calc R . . C4 C 0.55349(15) 0.34046(14) 0.35872(16) 0.0261(3) Uani 1 1 d . . . C5 C 0.51496(19) 0.40344(19) 0.2479(2) 0.0406(5) Uani 1 1 d . . . H5 H 0.4470 0.3758 0.1949 0.049 Uiso 1 1 calc R . . C6 C 0.5771(2) 0.5079(2) 0.2151(3) 0.0608(7) Uani 1 1 d . . . H6 H 0.5516 0.5515 0.1391 0.073 Uiso 1 1 calc R . . C7 C 0.6758(3) 0.5482(2) 0.2931(4) 0.0697(9) Uani 1 1 d . . . H7 H 0.7182 0.6191 0.2702 0.084 Uiso 1 1 calc R . . C8 C 0.7124(2) 0.48559(19) 0.4037(4) 0.0660(7) Uani 1 1 d . . . H8 H 0.7793 0.5141 0.4576 0.079 Uiso 1 1 calc R . . C9 C 0.6520(2) 0.38052(19) 0.4373(2) 0.0446(5) Uani 1 1 d . . . H9 H 0.6781 0.3369 0.5130 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01938(15) 0.02772(16) 0.01892(15) 0.00169(14) -0.00064(18) -0.00374(10) O1 0.0344(6) 0.0477(7) 0.0206(5) -0.0048(5) 0.0088(5) -0.0137(6) N1 0.0186(6) 0.0441(8) 0.0184(6) -0.0009(5) 0.0011(5) -0.0025(5) C1 0.0217(5) 0.0253(5) 0.0199(6) 0.0011(6) 0.0007(7) 0.0002(4) O2 0.0283(6) 0.0529(7) 0.0188(5) -0.0077(5) 0.0002(4) -0.0117(6) N2 0.0248(6) 0.0433(8) 0.0192(6) 0.0027(6) 0.0015(5) -0.0024(5) C2 0.0270(8) 0.0486(10) 0.0232(7) -0.0012(7) -0.0067(6) 0.0006(7) O3 0.0275(6) 0.0320(6) 0.0654(10) 0.0125(6) -0.0082(6) -0.0009(5) N3 0.0191(5) 0.0333(5) 0.0188(5) 0.0007(6) -0.0015(6) 0.0000(4) C3 0.0209(8) 0.0520(11) 0.0253(8) 0.0011(7) 0.0044(6) -0.0025(7) C4 0.0233(6) 0.0252(6) 0.0296(7) 0.0026(5) 0.0071(5) -0.0020(5) C5 0.0343(9) 0.0429(11) 0.0446(11) 0.0170(8) 0.0049(7) 0.0049(7) C6 0.0516(13) 0.0472(12) 0.0836(18) 0.0380(13) 0.0181(13) 0.0080(10) C7 0.0525(14) 0.0326(10) 0.124(3) 0.0231(14) 0.0238(16) -0.0059(9) C8 0.0534(12) 0.0467(10) 0.0980(19) 0.0013(16) -0.0038(17) -0.0243(10) C9 0.0404(9) 0.0419(9) 0.0514(13) 0.0035(8) -0.0075(8) -0.0137(8) _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 O3 1.4450(13) . ? S1 O1 1.4540(12) . ? S1 O2 1.4570(12) . ? S1 C4 1.7707(16) . ? N1 C1 1.333(2) . ? C1 N2 1.333(2) . ? C1 N3 1.3338(16) . ? C2 N3 1.460(2) . ? N3 C3 1.459(2) . ? C4 C5 1.385(3) . ? C4 C9 1.387(3) . ? C5 C6 1.396(3) . ? C6 C7 1.386(5) . ? C7 C8 1.376(5) . ? C8 C9 1.395(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O1 112.74(10) . . ? O3 S1 O2 113.58(9) . . ? O1 S1 O2 111.02(7) . . ? O3 S1 C4 106.35(8) . . ? O1 S1 C4 106.41(8) . . ? O2 S1 C4 106.14(8) . . ? N1 C1 N2 118.21(11) . . ? N1 C1 N3 120.69(14) . . ? N2 C1 N3 121.11(14) . . ? C1 N3 C3 120.14(14) . . ? C1 N3 C2 120.17(14) . . ? C3 N3 C2 119.51(11) . . ? C5 C4 C9 120.77(17) . . ? C5 C4 S1 120.56(15) . . ? C9 C4 S1 118.66(14) . . ? C4 C5 C6 119.3(2) . . ? C7 C6 C5 120.2(2) . . ? C8 C7 C6 120.03(19) . . ? C7 C8 C9 120.5(3) . . ? C4 C9 C8 119.2(2) . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 29.37 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.512 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.107 #===END