# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cmr_ppb_sst_ch3cn _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Succinylsulfathiazole plymorph I' _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N3 O5 S2' _chemical_formula_sum 'C13 H13 N3 O5 S2' _chemical_formula_weight 355.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8478(4) _cell_length_b 13.3523(6) _cell_length_c 14.1584(6) _cell_angle_alpha 67.9870(10) _cell_angle_beta 77.1140(10) _cell_angle_gamma 74.6120(10) _cell_volume 1480.77(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9930 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 33.30 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.233 _exptl_crystal_size_mid 0.137 _exptl_crystal_size_min 0.126 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.390 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_T_max 0.952 _exptl_absorpt_process_details 'SADABS; BRUKER, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25736 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6458 _reflns_number_gt 5701 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.6870P] 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 6458 _refine_ls_number_parameters 439 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_restrained_S_all 0.873 _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 S3 S 0.68971(5) 0.30183(3) 0.07739(3) 0.02707(12) Uani 1 1 d . . . S4 S 0.73893(6) 0.53554(4) 0.08206(4) 0.03823(13) Uani 1 1 d . . . S1 S 0.46586(5) 0.79818(4) 0.31332(3) 0.03129(12) Uani 1 1 d . . . S2 S 0.50536(6) 0.53996(4) 0.33629(4) 0.03964(14) Uani 1 1 d . . . C18 C 0.33750(19) 0.24231(13) 0.36955(12) 0.0260(3) Uani 1 1 d . . . C21 C 0.54683(19) 0.27860(14) 0.18818(12) 0.0265(3) Uani 1 1 d . . . C23 C 0.3266(2) 0.34757(14) 0.29667(13) 0.0285(3) Uani 1 1 d . . . H23 H 0.2496 0.4058 0.3088 0.034 Uiso 1 1 calc R . . C17 C 0.14220(19) 0.28326(14) 0.51353(13) 0.0268(3) Uani 1 1 d . . . C11 C 0.6178(2) 0.60066(14) 0.37775(12) 0.0283(3) Uani 1 1 d . . . C24 C 0.8605(2) 0.40482(13) 0.11493(13) 0.0278(3) Uani 1 1 d . . . C4 C 0.84125(19) 0.87872(13) -0.18114(13) 0.0279(3) Uani 1 1 d . . . C5 C 0.70937(19) 0.90308(13) -0.01506(12) 0.0267(3) Uani 1 1 d . . . C1 C 1.1448(2) 0.90751(13) -0.42724(13) 0.0297(4) Uani 1 1 d . . . C22 C 0.4316(2) 0.36531(14) 0.20558(13) 0.0291(3) Uani 1 1 d . . . H22 H 0.4243 0.4354 0.1564 0.035 Uiso 1 1 calc R . . C16 C 0.0623(2) 0.22093(15) 0.61771(13) 0.0326(4) Uani 1 1 d . . . H16A H -0.0240 0.1953 0.6079 0.039 Uiso 1 1 calc R . . H16B H 0.1379 0.1566 0.6512 0.039 Uiso 1 1 calc R . . C9 C 0.5215(2) 0.80647(15) 0.11282(14) 0.0326(4) Uani 1 1 d . . . H9 H 0.4484 0.7611 0.1322 0.039 Uiso 1 1 calc R . . C15 C -0.0017(2) 0.28929(16) 0.68702(14) 0.0368(4) Uani 1 1 d . . . H15A H -0.0840 0.3502 0.6566 0.044 Uiso 1 1 calc R . . H15B H 0.0825 0.3200 0.6926 0.044 Uiso 1 1 calc R . . C8 C 0.5528(2) 0.84407(14) 0.18390(13) 0.0283(3) Uani 1 1 d . . . C6 C 0.7370(2) 0.94304(15) 0.05610(14) 0.0361(4) Uani 1 1 d . . . H6 H 0.8079 0.9900 0.0364 0.043 Uiso 1 1 calc R . . C2 C 1.0254(2) 0.86003(15) -0.33943(14) 0.0350(4) Uani 1 1 d . . . H2A H 1.0764 0.7887 -0.2964 0.042 Uiso 1 1 calc R . . H2B H 0.9425 0.8484 -0.3665 0.042 Uiso 1 1 calc R . . C20 C 0.5563(2) 0.17299(15) 0.26030(14) 0.0351(4) Uani 1 1 d . . . H20 H 0.6329 0.1147 0.2480 0.042 Uiso 1 1 calc R . . C10 C 0.5989(2) 0.83652(15) 0.01284(14) 0.0316(4) Uani 1 1 d . . . H10 H 0.5770 0.8122 -0.0353 0.038 Uiso 1 1 calc R . . C7 C 0.6600(2) 0.91330(15) 0.15534(14) 0.0359(4) Uani 1 1 d . . . H7 H 0.6795 0.9394 0.2029 0.043 Uiso 1 1 calc R . . C19 C 0.4515(2) 0.15518(15) 0.35012(14) 0.0359(4) Uani 1 1 d . . . H19 H 0.4569 0.0845 0.3981 0.043 Uiso 1 1 calc R . . C14 C -0.0683(2) 0.22313(16) 0.79295(14) 0.0336(4) Uani 1 1 d . . . C12 C 0.7460(3) 0.41821(16) 0.42074(16) 0.0403(4) Uani 1 1 d . . . H12 H 0.8236 0.3577 0.4482 0.048 Uiso 1 1 calc R . . C3 C 0.9518(3) 0.93154(16) -0.27426(15) 0.0409(5) Uani 1 1 d . . . H3A H 0.8935 1.0007 -0.3158 0.049 Uiso 1 1 calc R . . H3B H 1.0351 0.9481 -0.2515 0.049 Uiso 1 1 calc R . . C26 C 0.8718(2) 0.58829(16) 0.11451(17) 0.0427(5) Uani 1 1 d . . . H26 H 0.8565 0.6613 0.1108 0.051 Uiso 1 1 calc R . . C25 C 0.9982(2) 0.51151(16) 0.14534(17) 0.0395(4) Uani 1 1 d . . . H25 H 1.0827 0.5252 0.1644 0.047 Uiso 1 1 calc R . . C13 C 0.6311(3) 0.41326(16) 0.37775(17) 0.0437(5) Uani 1 1 d . . . H13 H 0.6193 0.3494 0.3707 0.052 Uiso 1 1 calc R . . O8 O 0.11936(16) 0.38385(10) 0.47788(10) 0.0348(3) Uani 1 1 d . . . O3 O 0.79739(15) 0.79422(11) -0.16695(10) 0.0352(3) Uani 1 1 d . . . O9 O 0.73327(17) 0.20254(11) 0.05094(10) 0.0384(3) Uani 1 1 d . . . O10 O 0.62710(16) 0.40205(11) 0.00074(10) 0.0389(3) Uani 1 1 d . . . O7 O -0.05616(18) 0.12511(12) 0.82559(11) 0.0419(3) Uani 1 1 d . . . O4 O 0.43869(18) 0.88749(11) 0.35294(11) 0.0447(3) Uani 1 1 d . . . O5 O 0.32950(16) 0.75671(13) 0.31699(11) 0.0432(3) Uani 1 1 d . . . O2 O 1.2037(2) 0.84316(13) -0.48368(13) 0.0535(4) Uani 1 1 d . . . O1 O 1.1874(2) 0.99112(12) -0.44443(13) 0.0539(4) Uani 1 1 d . . . O6 O -0.1414(3) 0.28795(15) 0.84775(13) 0.0631(5) Uani 1 1 d . . . N2 N 0.60059(18) 0.70395(12) 0.37255(11) 0.0321(3) Uani 1 1 d . . . N4 N 0.23711(18) 0.21590(12) 0.46371(11) 0.0304(3) Uani 1 1 d . . . N5 N 0.84284(17) 0.30998(12) 0.11405(12) 0.0301(3) Uani 1 1 d . . . N1 N 0.79566(19) 0.93562(12) -0.11416(11) 0.0332(3) Uani 1 1 d . . . N6 N 0.99057(18) 0.40906(13) 0.14614(13) 0.0327(3) Uani 1 1 d . . . N3 N 0.73796(19) 0.52349(13) 0.42032(12) 0.0346(3) Uani 1 1 d . . . H2C H 1.269(4) 0.874(2) -0.529(3) 0.072(9) Uiso 1 1 d . . . H1 H 0.838(3) 0.993(2) -0.1281(19) 0.050(7) Uiso 1 1 d . . . H6B H -0.169(4) 0.245(3) 0.912(3) 0.080(10) Uiso 1 1 d . . . H4 H 0.245(3) 0.147(2) 0.4938(18) 0.041(6) Uiso 1 1 d . . . H3 H 0.796(3) 0.543(2) 0.450(2) 0.051(7) Uiso 1 1 d . . . H6A H 1.063(4) 0.343(2) 0.161(2) 0.068(8) 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 S3 0.0284(2) 0.0336(2) 0.0196(2) -0.01042(16) 0.00422(15) -0.01092(16) S4 0.0346(2) 0.0309(2) 0.0473(3) -0.0132(2) -0.0069(2) -0.00241(18) S1 0.0299(2) 0.0346(2) 0.0242(2) -0.01044(17) 0.00705(16) -0.00622(17) S2 0.0391(3) 0.0407(3) 0.0467(3) -0.0182(2) -0.0112(2) -0.0108(2) C18 0.0282(8) 0.0311(8) 0.0203(7) -0.0106(6) 0.0046(6) -0.0122(6) C21 0.0265(8) 0.0336(8) 0.0204(7) -0.0099(6) 0.0025(6) -0.0113(6) C23 0.0300(8) 0.0287(8) 0.0254(8) -0.0098(6) 0.0016(6) -0.0069(6) C17 0.0268(8) 0.0344(8) 0.0232(8) -0.0130(7) 0.0014(6) -0.0120(6) C11 0.0314(8) 0.0337(8) 0.0199(7) -0.0082(6) 0.0032(6) -0.0137(7) C24 0.0277(8) 0.0280(8) 0.0241(8) -0.0074(6) 0.0030(6) -0.0076(6) C4 0.0267(8) 0.0274(8) 0.0254(8) -0.0086(6) 0.0006(6) -0.0024(6) C5 0.0283(8) 0.0256(7) 0.0218(8) -0.0070(6) 0.0029(6) -0.0050(6) C1 0.0364(9) 0.0259(8) 0.0218(8) -0.0067(6) 0.0021(7) -0.0049(6) C22 0.0320(8) 0.0298(8) 0.0224(8) -0.0058(6) -0.0002(6) -0.0087(6) C16 0.0381(9) 0.0360(9) 0.0257(8) -0.0143(7) 0.0092(7) -0.0160(7) C9 0.0277(8) 0.0401(9) 0.0299(9) -0.0123(7) 0.0038(7) -0.0121(7) C15 0.0455(10) 0.0393(10) 0.0296(9) -0.0176(8) 0.0146(8) -0.0228(8) C8 0.0272(8) 0.0291(8) 0.0235(8) -0.0076(6) 0.0026(6) -0.0042(6) C6 0.0458(10) 0.0358(9) 0.0291(9) -0.0110(7) 0.0055(8) -0.0207(8) C2 0.0439(10) 0.0364(9) 0.0260(9) -0.0138(7) 0.0076(7) -0.0154(8) C20 0.0374(9) 0.0295(8) 0.0310(9) -0.0105(7) 0.0090(7) -0.0053(7) C10 0.0293(8) 0.0410(9) 0.0280(9) -0.0157(7) 0.0023(7) -0.0119(7) C7 0.0470(10) 0.0383(9) 0.0260(9) -0.0139(7) 0.0041(7) -0.0172(8) C19 0.0425(10) 0.0268(8) 0.0290(9) -0.0065(7) 0.0092(8) -0.0078(7) C14 0.0373(9) 0.0441(10) 0.0275(9) -0.0194(8) 0.0102(7) -0.0228(8) C12 0.0475(11) 0.0304(9) 0.0431(11) -0.0098(8) -0.0101(9) -0.0084(8) C3 0.0519(11) 0.0329(9) 0.0314(9) -0.0131(8) 0.0156(8) -0.0121(8) C26 0.0460(11) 0.0308(9) 0.0540(13) -0.0166(9) -0.0056(9) -0.0099(8) C25 0.0422(10) 0.0351(9) 0.0453(11) -0.0143(8) -0.0059(8) -0.0138(8) C13 0.0517(12) 0.0362(10) 0.0508(12) -0.0185(9) -0.0107(10) -0.0122(9) O8 0.0434(7) 0.0318(6) 0.0281(6) -0.0119(5) 0.0018(5) -0.0089(5) O3 0.0325(6) 0.0363(7) 0.0386(7) -0.0181(6) 0.0058(5) -0.0105(5) O9 0.0458(8) 0.0440(7) 0.0322(7) -0.0226(6) 0.0099(6) -0.0185(6) O10 0.0396(7) 0.0465(8) 0.0232(6) -0.0048(5) -0.0005(5) -0.0097(6) O7 0.0508(8) 0.0444(8) 0.0315(7) -0.0122(6) 0.0048(6) -0.0206(6) O4 0.0545(9) 0.0383(7) 0.0348(7) -0.0181(6) 0.0135(6) -0.0062(6) O5 0.0282(6) 0.0571(9) 0.0369(7) -0.0115(6) 0.0059(5) -0.0115(6) O2 0.0717(11) 0.0478(9) 0.0428(9) -0.0284(7) 0.0286(8) -0.0259(8) O1 0.0681(11) 0.0359(7) 0.0529(9) -0.0207(7) 0.0266(8) -0.0232(7) O6 0.1003(14) 0.0595(10) 0.0387(9) -0.0338(8) 0.0379(9) -0.0452(10) N2 0.0377(8) 0.0315(7) 0.0275(7) -0.0079(6) -0.0018(6) -0.0129(6) N4 0.0370(8) 0.0281(7) 0.0242(7) -0.0096(6) 0.0094(6) -0.0134(6) N5 0.0282(7) 0.0288(7) 0.0315(7) -0.0085(6) 0.0000(6) -0.0086(6) N1 0.0423(8) 0.0295(7) 0.0259(7) -0.0107(6) 0.0105(6) -0.0149(6) N6 0.0293(7) 0.0292(7) 0.0400(9) -0.0117(6) -0.0039(6) -0.0073(6) N3 0.0391(8) 0.0325(8) 0.0338(8) -0.0076(6) -0.0081(7) -0.0126(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 S3 O10 1.4358(13) . ? S3 O9 1.4433(13) . ? S3 N5 1.5972(15) . ? S3 C21 1.7645(16) . ? S4 C26 1.736(2) . ? S4 C24 1.7430(17) . ? S1 O5 1.4387(15) . ? S1 O4 1.4435(14) . ? S1 N2 1.6019(16) . ? S1 C8 1.7621(17) . ? S2 C13 1.730(2) . ? S2 C11 1.7422(17) . ? C18 C23 1.391(2) . ? C18 C19 1.393(2) . ? C18 N4 1.406(2) . ? C21 C22 1.384(2) . ? C21 C20 1.391(2) . ? C23 C22 1.391(2) . ? C17 O8 1.222(2) . ? C17 N4 1.350(2) . ? C17 C16 1.515(2) . ? C11 N2 1.322(2) . ? C11 N3 1.340(2) . ? C24 N5 1.321(2) . ? C24 N6 1.343(2) . ? C4 O3 1.221(2) . ? C4 N1 1.359(2) . ? C4 C3 1.512(2) . ? C5 C10 1.388(2) . ? C5 C6 1.393(3) . ? C5 N1 1.408(2) . ? C1 O1 1.194(2) . ? C1 O2 1.319(2) . ? C1 C2 1.497(2) . ? C16 C15 1.505(2) . ? C9 C8 1.385(3) . ? C9 C10 1.386(2) . ? C15 C14 1.505(2) . ? C8 C7 1.389(2) . ? C6 C7 1.377(3) . ? C2 C3 1.500(3) . ? C20 C19 1.378(2) . ? C14 O7 1.197(2) . ? C14 O6 1.323(2) . ? C12 C13 1.323(3) . ? C12 N3 1.386(2) . ? C26 C25 1.329(3) . ? C25 N6 1.383(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 O10 S3 O9 117.13(9) . . ? O10 S3 N5 112.54(8) . . ? O9 S3 N5 105.70(8) . . ? O10 S3 C21 108.29(8) . . ? O9 S3 C21 107.03(8) . . ? N5 S3 C21 105.42(8) . . ? C26 S4 C24 90.75(9) . . ? O5 S1 O4 116.75(9) . . ? O5 S1 N2 112.47(8) . . ? O4 S1 N2 106.19(9) . . ? O5 S1 C8 107.87(9) . . ? O4 S1 C8 107.70(8) . . ? N2 S1 C8 105.19(8) . . ? C13 S2 C11 90.87(9) . . ? C23 C18 C19 119.83(15) . . ? C23 C18 N4 124.00(15) . . ? C19 C18 N4 116.16(15) . . ? C22 C21 C20 120.38(15) . . ? C22 C21 S3 120.45(12) . . ? C20 C21 S3 119.09(13) . . ? C18 C23 C22 119.66(16) . . ? O8 C17 N4 123.99(16) . . ? O8 C17 C16 123.20(15) . . ? N4 C17 C16 112.79(14) . . ? N2 C11 N3 120.31(16) . . ? N2 C11 S2 130.62(14) . . ? N3 C11 S2 109.06(13) . . ? N5 C24 N6 119.54(15) . . ? N5 C24 S4 131.14(13) . . ? N6 C24 S4 109.32(12) . . ? O3 C4 N1 123.33(16) . . ? O3 C4 C3 124.17(16) . . ? N1 C4 C3 112.51(15) . . ? C10 C5 C6 119.95(16) . . ? C10 C5 N1 123.37(16) . . ? C6 C5 N1 116.67(15) . . ? O1 C1 O2 122.74(17) . . ? O1 C1 C2 125.73(16) . . ? O2 C1 C2 111.49(15) . . ? C21 C22 C23 120.00(15) . . ? C15 C16 C17 113.22(14) . . ? C8 C9 C10 120.01(16) . . ? C16 C15 C14 112.27(15) . . ? C9 C8 C7 120.43(16) . . ? C9 C8 S1 120.24(13) . . ? C7 C8 S1 119.23(14) . . ? C7 C6 C5 120.36(17) . . ? C1 C2 C3 113.62(15) . . ? C19 C20 C21 119.63(16) . . ? C9 C10 C5 119.65(16) . . ? C6 C7 C8 119.54(17) . . ? C20 C19 C18 120.47(16) . . ? O7 C14 O6 123.46(17) . . ? O7 C14 C15 125.72(17) . . ? O6 C14 C15 110.81(16) . . ? C13 C12 N3 112.58(18) . . ? C2 C3 C4 113.09(15) . . ? C25 C26 S4 111.61(14) . . ? C26 C25 N6 112.84(17) . . ? C12 C13 S2 111.87(15) . . ? C11 N2 S1 120.37(13) . . ? C17 N4 C18 129.32(15) . . ? C24 N5 S3 120.92(12) . . ? C4 N1 C5 127.27(15) . . ? C24 N6 C25 115.46(16) . . ? C11 N3 C12 115.60(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.328 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 943847' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cmr_ppb_sst_ea1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Succinylsulfathiazole plymorph II' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 N3 O5 S2' _chemical_formula_weight 355.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 11.351(3) _cell_length_b 8.577(2) _cell_length_c 16.684(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.483(5) _cell_angle_gamma 90.00 _cell_volume 1549.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2263 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.55 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.331 _exptl_crystal_size_mid 0.295 _exptl_crystal_size_min 0.045 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.884 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details 'SADABS; BRUKER, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14705 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3370 _reflns_number_gt 2241 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.2726P] 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 3370 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 0.895 _refine_ls_restrained_S_all 0.895 _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 0.27115(6) 0.21515(9) 0.13585(4) 0.0343(2) Uani 1 1 d . . . S2 S 0.22012(7) -0.15157(10) 0.07313(5) 0.0419(2) Uani 1 1 d . . . C11 C 0.1250(2) -0.0204(3) 0.10286(15) 0.0298(6) Uani 1 1 d . . . C8 C 0.3444(2) 0.2170(3) 0.24474(18) 0.0313(6) Uani 1 1 d . . . C5 C 0.4564(2) 0.2230(3) 0.41736(18) 0.0313(6) Uani 1 1 d . . . C1 C 0.8703(3) 0.2666(4) 0.66828(17) 0.0342(6) Uani 1 1 d . . . C9 C 0.4492(2) 0.1288(3) 0.28084(18) 0.0316(6) Uani 1 1 d . . . H9 H 0.4819 0.0672 0.2468 0.038 Uiso 1 1 calc R . . C10 C 0.5060(2) 0.1309(3) 0.36669(17) 0.0312(6) Uani 1 1 d . . . H10 H 0.5764 0.0715 0.3903 0.037 Uiso 1 1 calc R . . C6 C 0.3506(3) 0.3117(4) 0.38062(19) 0.0381(7) Uani 1 1 d . . . H6 H 0.3170 0.3724 0.4145 0.046 Uiso 1 1 calc R . . C2 C 0.7757(3) 0.1780(4) 0.69530(19) 0.0394(7) Uani 1 1 d . . . H2A H 0.7880 0.1960 0.7547 0.047 Uiso 1 1 calc R . . H2B H 0.7857 0.0674 0.6873 0.047 Uiso 1 1 calc R . . C4 C 0.6179(2) 0.1827(3) 0.55423(18) 0.0315(6) Uani 1 1 d . . . C3 C 0.6461(2) 0.2273(4) 0.64569(17) 0.0333(6) Uani 1 1 d . . . H3A H 0.5871 0.1777 0.6691 0.040 Uiso 1 1 calc R . . H3B H 0.6380 0.3392 0.6502 0.040 Uiso 1 1 calc R . . C7 C 0.2955(3) 0.3103(4) 0.29502(19) 0.0385(7) Uani 1 1 d . . . H7 H 0.2261 0.3713 0.2710 0.046 Uiso 1 1 calc R . . C12 C 0.0115(3) -0.2475(4) 0.0793(2) 0.0433(8) Uani 1 1 d . . . H12 H -0.0564 -0.3101 0.0768 0.052 Uiso 1 1 calc R . . C13 C 0.1123(3) -0.2978(4) 0.0623(2) 0.0473(8) Uani 1 1 d . . . H13 H 0.1233 -0.3995 0.0466 0.057 Uiso 1 1 calc R . . O3 O 0.69120(18) 0.1101(2) 0.52831(13) 0.0395(5) Uani 1 1 d . . . O5 O 0.34814(18) 0.1268(3) 0.09728(12) 0.0438(6) Uani 1 1 d . . . O1 O 0.85360(19) 0.4006(2) 0.64357(14) 0.0427(5) Uani 1 1 d . . . O2 O 0.9728(2) 0.1890(3) 0.67435(17) 0.0542(7) Uani 1 1 d . . . O4 O 0.2435(2) 0.3735(3) 0.11002(14) 0.0506(6) Uani 1 1 d . . . N1 N 0.5072(2) 0.2347(3) 0.50475(16) 0.0352(6) Uani 1 1 d . . . N3 N 0.0193(2) -0.0915(3) 0.10122(16) 0.0354(6) Uani 1 1 d . . . N2 N 0.1416(2) 0.1292(3) 0.12417(14) 0.0326(5) Uani 1 1 d . . . H1 H 0.466(3) 0.284(4) 0.528(2) 0.035(9) Uiso 1 1 d . . . H2C H 1.015(5) 0.258(6) 0.657(3) 0.109(19) Uiso 1 1 d . . . H3 H -0.031(3) -0.043(4) 0.1138(19) 0.043(10) 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 0.0281(4) 0.0434(4) 0.0331(4) 0.0093(3) 0.0115(3) -0.0013(3) S2 0.0392(4) 0.0483(5) 0.0426(5) -0.0006(3) 0.0190(3) 0.0114(3) C11 0.0264(13) 0.0406(17) 0.0207(13) 0.0043(11) 0.0046(10) 0.0072(12) C8 0.0256(13) 0.0362(15) 0.0332(15) 0.0036(12) 0.0107(11) -0.0012(11) C5 0.0247(13) 0.0369(16) 0.0339(15) -0.0007(12) 0.0111(11) -0.0033(11) C1 0.0276(14) 0.0452(18) 0.0286(15) 0.0001(12) 0.0065(11) -0.0022(12) C9 0.0278(14) 0.0342(15) 0.0360(15) 0.0005(12) 0.0144(11) -0.0002(11) C10 0.0245(13) 0.0342(15) 0.0352(15) 0.0023(11) 0.0096(11) 0.0030(11) C6 0.0285(14) 0.0481(18) 0.0406(17) -0.0065(13) 0.0144(12) 0.0068(13) C2 0.0345(16) 0.0513(19) 0.0317(15) 0.0122(13) 0.0090(12) -0.0008(14) C4 0.0259(14) 0.0359(16) 0.0345(15) 0.0044(12) 0.0117(11) -0.0043(11) C3 0.0278(14) 0.0428(17) 0.0329(15) 0.0046(12) 0.0147(12) -0.0046(12) C7 0.0259(14) 0.0445(18) 0.0440(18) 0.0017(13) 0.0089(12) 0.0074(12) C12 0.0395(17) 0.0395(18) 0.0467(19) -0.0040(14) 0.0066(14) 0.0022(14) C13 0.051(2) 0.0411(18) 0.049(2) -0.0059(15) 0.0136(15) 0.0090(15) O3 0.0340(11) 0.0486(13) 0.0380(11) 0.0010(9) 0.0140(9) 0.0084(9) O5 0.0333(11) 0.0678(16) 0.0347(11) 0.0037(10) 0.0168(9) -0.0022(10) O1 0.0339(11) 0.0381(12) 0.0595(14) 0.0037(10) 0.0192(10) -0.0014(9) O2 0.0324(12) 0.0544(16) 0.0779(18) 0.0231(13) 0.0200(12) 0.0093(11) O4 0.0506(14) 0.0480(14) 0.0513(14) 0.0213(11) 0.0124(11) -0.0019(11) N1 0.0249(12) 0.0496(16) 0.0328(14) -0.0033(11) 0.0111(10) 0.0044(11) N3 0.0277(13) 0.0395(15) 0.0375(14) -0.0028(11) 0.0077(10) 0.0048(11) N2 0.0241(12) 0.0386(14) 0.0355(13) 0.0017(10) 0.0094(9) 0.0009(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 O4 1.431(2) . ? S1 O5 1.446(2) . ? S1 N2 1.603(2) . ? S1 C8 1.756(3) . ? S2 C13 1.724(4) . ? S2 C11 1.732(3) . ? C11 N2 1.330(4) . ? C11 N3 1.339(4) . ? C8 C9 1.386(4) . ? C8 C7 1.390(4) . ? C5 C10 1.393(4) . ? C5 C6 1.398(4) . ? C5 N1 1.401(4) . ? C1 O1 1.216(4) . ? C1 O2 1.317(4) . ? C1 C2 1.492(4) . ? C9 C10 1.383(4) . ? C6 C7 1.376(4) . ? C2 C3 1.515(4) . ? C4 O3 1.218(3) . ? C4 N1 1.355(4) . ? C4 C3 1.511(4) . ? C12 C13 1.331(4) . ? C12 N3 1.383(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 O4 S1 O5 118.06(14) . . ? O4 S1 N2 106.85(13) . . ? O5 S1 N2 111.09(13) . . ? O4 S1 C8 107.20(14) . . ? O5 S1 C8 107.67(13) . . ? N2 S1 C8 105.18(12) . . ? C13 S2 C11 91.06(15) . . ? N2 C11 N3 119.9(2) . . ? N2 C11 S2 130.8(2) . . ? N3 C11 S2 109.3(2) . . ? C9 C8 C7 119.9(3) . . ? C9 C8 S1 121.5(2) . . ? C7 C8 S1 118.6(2) . . ? C10 C5 C6 119.5(3) . . ? C10 C5 N1 123.9(3) . . ? C6 C5 N1 116.6(3) . . ? O1 C1 O2 123.2(3) . . ? O1 C1 C2 122.0(3) . . ? O2 C1 C2 114.7(3) . . ? C10 C9 C8 121.0(3) . . ? C9 C10 C5 119.2(3) . . ? C7 C6 C5 120.9(3) . . ? C1 C2 C3 111.2(2) . . ? O3 C4 N1 124.0(3) . . ? O3 C4 C3 121.8(3) . . ? N1 C4 C3 114.1(2) . . ? C4 C3 C2 111.0(2) . . ? C6 C7 C8 119.5(3) . . ? C13 C12 N3 112.3(3) . . ? C12 C13 S2 111.7(3) . . ? C4 N1 C5 128.8(3) . . ? C11 N3 C12 115.6(3) . . ? C11 N2 S1 121.8(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.425 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 943848' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cmr_ppb_sst_h2o _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Succinylsulfathiazole mono hydrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 N3 O6 S2' _chemical_formula_weight 373.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 16.190(6) _cell_length_b 5.1460(14) _cell_length_c 19.449(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.028(17) _cell_angle_gamma 90.00 _cell_volume 1616.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6266 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 26.28 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.245 _exptl_crystal_size_mid 0.086 _exptl_crystal_size_min 0.044 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.365 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.914 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'SADABS; BRUKER, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13143 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3322 _reflns_number_gt 2672 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^+0.7429P] 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 3322 _refine_ls_number_parameters 237 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1123 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.03365(12) 0.7643(4) 0.40358(9) 0.0399(4) Uani 1 1 d . . . C2 C 0.97732(13) 0.5381(4) 0.39067(10) 0.0444(5) Uani 1 1 d . . . H2B H 0.9329 0.5493 0.4215 0.053 Uiso 1 1 calc R . . H2A H 1.0080 0.3799 0.4017 0.053 Uiso 1 1 calc R . . C3 C 0.93994(14) 0.5194(4) 0.31760(10) 0.0464(5) Uani 1 1 d . . . H3B H 0.9133 0.3515 0.3111 0.056 Uiso 1 1 calc R . . H3A H 0.9839 0.5293 0.2863 0.056 Uiso 1 1 calc R . . C4 C 0.87733(12) 0.7302(4) 0.29924(9) 0.0402(4) Uani 1 1 d . . . C5 C 0.80325(11) 0.9317(3) 0.19669(9) 0.0358(4) Uani 1 1 d . . . C6 C 0.79677(12) 0.9186(4) 0.12536(10) 0.0403(4) Uani 1 1 d . . . H6 H 0.8292 0.8004 0.1031 0.048 Uiso 1 1 calc R . . C7 C 0.74344(12) 1.0768(4) 0.08729(10) 0.0444(5) Uani 1 1 d . . . H7 H 0.7398 1.0664 0.0394 0.053 Uiso 1 1 calc R . . C8 C 0.69503(12) 1.2521(4) 0.12005(10) 0.0418(4) Uani 1 1 d . . . C9 C 0.70102(14) 1.2666(4) 0.19052(11) 0.0511(5) Uani 1 1 d . . . H9 H 0.6681 1.3845 0.2124 0.061 Uiso 1 1 calc R . . C10 C 0.75512(13) 1.1088(4) 0.22962(10) 0.0472(5) Uani 1 1 d . . . H10 H 0.7591 1.1214 0.2774 0.057 Uiso 1 1 calc R . . C11 C 0.48764(13) 1.2146(4) 0.09038(11) 0.0486(5) Uani 1 1 d . . . C12 C 0.36871(17) 1.0182(6) 0.11846(16) 0.0748(8) Uani 1 1 d . . . H12 H 0.3249 0.9014 0.1129 0.090 Uiso 1 1 calc R . . C13 C 0.3769(2) 1.1892(6) 0.16876(18) 0.0895(10) Uani 1 1 d . . . H13 H 0.3400 1.2053 0.2031 0.107 Uiso 1 1 calc R . . H1 H 0.8890(13) 0.650(4) 0.1996(10) 0.074(8) Uiso 1 1 d D . . H3 H 0.4361(17) 0.916(4) 0.0341(9) 0.082(9) Uiso 1 1 d D . . H1A H 1.0965(17) 0.897(6) 0.4771(14) 0.076(9) Uiso 1 1 d . . . H6A H 0.1724(19) 0.107(6) 0.5620(18) 0.087(10) Uiso 1 1 d . . . H6B H 0.222(2) 0.033(7) 0.5161(19) 0.115(14) Uiso 1 1 d . . . N1 N 0.86015(10) 0.7615(3) 0.23106(8) 0.0395(4) Uani 1 1 d D . . N2 N 0.54849(10) 1.2502(3) 0.04966(9) 0.0483(4) Uani 1 1 d . . . N3 N 0.43162(11) 1.0308(4) 0.07523(10) 0.0544(5) Uani 1 1 d D . . O1 O 1.06233(11) 0.7739(4) 0.46832(7) 0.0599(4) Uani 1 1 d . . . O2 O 1.05215(10) 0.9170(3) 0.36048(7) 0.0535(4) Uani 1 1 d . . . O3 O 0.84474(11) 0.8584(4) 0.34215(7) 0.0646(5) Uani 1 1 d . . . O4 O 0.65821(10) 1.5054(3) 0.00793(9) 0.0675(5) Uani 1 1 d . . . O5 O 0.59812(11) 1.6518(3) 0.11414(10) 0.0722(5) Uani 1 1 d . . . O6 O 0.17579(12) 0.1044(4) 0.51801(9) 0.0672(5) Uani 1 1 d . . . S1 S 0.62275(3) 1.44343(10) 0.07128(3) 0.05195(18) Uani 1 1 d . . . S2 S 0.46370(5) 1.37979(14) 0.16359(4) 0.0780(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0439(11) 0.0413(9) 0.0345(10) 0.0066(8) 0.0045(8) 0.0085(8) C2 0.0507(12) 0.0410(10) 0.0410(10) 0.0135(8) -0.0007(9) 0.0034(9) C3 0.0545(12) 0.0391(10) 0.0445(11) 0.0030(8) -0.0043(9) 0.0030(9) C4 0.0408(11) 0.0445(10) 0.0350(10) 0.0008(8) 0.0014(8) -0.0013(8) C5 0.0353(10) 0.0364(9) 0.0354(9) -0.0004(7) 0.0001(7) -0.0005(7) C6 0.0412(11) 0.0441(10) 0.0358(9) -0.0018(8) 0.0039(8) 0.0037(8) C7 0.0451(11) 0.0497(11) 0.0379(10) 0.0043(8) -0.0005(8) 0.0016(9) C8 0.0388(10) 0.0362(9) 0.0497(11) 0.0050(8) -0.0023(8) -0.0003(8) C9 0.0525(13) 0.0476(11) 0.0528(12) -0.0087(9) 0.0005(10) 0.0134(9) C10 0.0526(12) 0.0518(11) 0.0369(10) -0.0067(9) 0.0004(9) 0.0085(9) C11 0.0456(12) 0.0453(11) 0.0546(12) 0.0172(9) 0.0023(10) 0.0116(9) C12 0.0601(16) 0.0700(16) 0.098(2) 0.0295(16) 0.0321(15) 0.0094(13) C13 0.097(2) 0.0783(19) 0.100(2) 0.0260(18) 0.0555(19) 0.0208(17) N1 0.0435(9) 0.0421(8) 0.0326(8) -0.0019(6) 0.0008(7) 0.0068(7) N2 0.0377(9) 0.0513(10) 0.0554(10) 0.0131(8) 0.0013(8) 0.0028(7) N3 0.0417(10) 0.0568(11) 0.0657(12) 0.0185(9) 0.0104(9) 0.0030(9) O1 0.0713(11) 0.0727(11) 0.0347(8) 0.0077(7) -0.0038(7) -0.0143(9) O2 0.0680(10) 0.0491(8) 0.0434(8) 0.0137(6) 0.0032(7) -0.0096(7) O3 0.0712(11) 0.0902(12) 0.0327(7) -0.0003(8) 0.0047(7) 0.0329(10) O4 0.0499(9) 0.0730(11) 0.0786(11) 0.0407(9) -0.0022(8) -0.0048(8) O5 0.0666(11) 0.0379(8) 0.1106(15) 0.0004(8) -0.0049(10) 0.0117(7) O6 0.0598(12) 0.1013(15) 0.0404(9) -0.0123(9) 0.0040(8) -0.0043(10) S1 0.0446(3) 0.0411(3) 0.0691(4) 0.0165(2) -0.0041(3) 0.0023(2) S2 0.0975(6) 0.0639(4) 0.0755(5) 0.0041(3) 0.0278(4) 0.0137(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.202(2) . ? C1 O1 1.312(2) . ? C1 C2 1.489(3) . ? C2 C3 1.508(3) . ? C2 H2B 0.9700 . ? C2 H2A 0.9700 . ? C3 C4 1.510(3) . ? C3 H3B 0.9700 . ? C3 H3A 0.9700 . ? C4 O3 1.213(2) . ? C4 N1 1.345(2) . ? C5 C10 1.385(3) . ? C5 C6 1.386(3) . ? C5 N1 1.406(2) . ? C6 C7 1.366(3) . ? C6 H6 0.9300 . ? C7 C8 1.380(3) . ? C7 H7 0.9300 . ? C8 C9 1.369(3) . ? C8 S1 1.756(2) . ? C9 C10 1.383(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 N2 1.319(3) . ? C11 N3 1.329(3) . ? C11 S2 1.726(2) . ? C12 C13 1.316(4) . ? C12 N3 1.367(3) . ? C12 H12 0.9300 . ? C13 S2 1.723(3) . ? C13 H13 0.9300 . ? N1 H1 0.9798(11) . ? N2 S1 1.5939(19) . ? N3 H3 1.0000(11) . ? O1 H1A 0.85(3) . ? O4 S1 1.4313(18) . ? O5 S1 1.4320(18) . ? O6 H6A 0.86(3) . ? O6 H6B 0.84(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 C1 O1 123.8(2) . . ? O2 C1 C2 124.96(18) . . ? O1 C1 C2 111.26(16) . . ? C1 C2 C3 114.16(16) . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? H2B C2 H2A 107.6 . . ? C2 C3 C4 113.28(17) . . ? C2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? H3B C3 H3A 107.7 . . ? O3 C4 N1 122.88(18) . . ? O3 C4 C3 123.03(17) . . ? N1 C4 C3 114.08(16) . . ? C10 C5 C6 119.31(17) . . ? C10 C5 N1 124.15(17) . . ? C6 C5 N1 116.53(16) . . ? C7 C6 C5 120.94(18) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 119.81(19) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 119.68(18) . . ? C9 C8 S1 120.52(16) . . ? C7 C8 S1 119.72(16) . . ? C8 C9 C10 121.08(19) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C5 119.17(19) . . ? C9 C10 H10 120.4 . . ? C5 C10 H10 120.4 . . ? N2 C11 N3 119.5(2) . . ? N2 C11 S2 130.34(18) . . ? N3 C11 S2 110.13(16) . . ? C13 C12 N3 112.7(3) . . ? C13 C12 H12 123.7 . . ? N3 C12 H12 123.7 . . ? C12 C13 S2 112.1(2) . . ? C12 C13 H13 123.9 . . ? S2 C13 H13 123.9 . . ? C4 N1 C5 128.79(16) . . ? C4 N1 H1 118.1(15) . . ? C5 N1 H1 113.1(15) . . ? C11 N2 S1 120.62(17) . . ? C11 N3 C12 115.1(2) . . ? C11 N3 H3 120.7(17) . . ? C12 N3 H3 124.2(17) . . ? C1 O1 H1A 113.8(19) . . ? H6A O6 H6B 100(3) . . ? O4 S1 O5 118.64(11) . . ? O4 S1 N2 104.63(10) . . ? O5 S1 N2 112.65(10) . . ? O4 S1 C8 107.30(10) . . ? O5 S1 C8 107.93(11) . . ? N2 S1 C8 104.74(9) . . ? C13 S2 C11 89.96(14) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.302 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 943849' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cmr_ppb_sst_acetone _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Succinylsulfathiazole acetone solvate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H32 N6 O11 S4' _chemical_formula_weight 768.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5229(4) _cell_length_b 14.5887(7) _cell_length_c 15.2327(7) _cell_angle_alpha 64.7770(10) _cell_angle_beta 78.1610(10) _cell_angle_gamma 82.0860(10) _cell_volume 1674.27(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9899 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 25.14 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.592 _exptl_crystal_size_mid 0.408 _exptl_crystal_size_min 0.109 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.353 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.841 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_process_details 'SADABS; BRUKER, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24403 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 25.14 _reflns_number_total 5957 _reflns_number_gt 5375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0240P)^2^+9.8739P] 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 5957 _refine_ls_number_parameters 455 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0718 _refine_ls_wR_factor_ref 0.1510 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0878(4) -0.2048(3) 0.5038(3) 0.0177(8) Uani 1 1 d . . . C2 C 0.2441(4) -0.1539(3) 0.4683(3) 0.0178(8) Uani 1 1 d . . . H2A H 0.2831 -0.1457 0.4011 0.021 Uiso 1 1 calc R . . H2B H 0.3225 -0.1974 0.5084 0.021 Uiso 1 1 calc R . . C3 C 0.2304(4) -0.0507(3) 0.4722(3) 0.0170(8) Uani 1 1 d . . . H3A H 0.1364 -0.0125 0.4451 0.020 Uiso 1 1 calc R . . H3B H 0.2159 -0.0600 0.5403 0.020 Uiso 1 1 calc R . . C4 C 0.3774(4) 0.0096(3) 0.4156(3) 0.0151(7) Uani 1 1 d . . . C6 C 0.4162(4) 0.2754(3) 0.3661(3) 0.0176(8) Uani 1 1 d . . . H6A H 0.3174 0.2810 0.4036 0.021 Uiso 1 1 calc R . . C7 C 0.5151(5) 0.3564(3) 0.3234(3) 0.0182(8) Uani 1 1 d . . . H7 H 0.4830 0.4161 0.3316 0.022 Uiso 1 1 calc R . . C8 C 0.6623(4) 0.3472(3) 0.2682(3) 0.0165(7) Uani 1 1 d . . . C9 C 0.7089(5) 0.2592(3) 0.2533(3) 0.0194(8) Uani 1 1 d . . . H9 H 0.8072 0.2544 0.2151 0.023 Uiso 1 1 calc R . . C10 C 0.6094(5) 0.1787(3) 0.2950(3) 0.0183(8) Uani 1 1 d . . . H10 H 0.6399 0.1202 0.2841 0.022 Uiso 1 1 calc R . . C11 C 0.7594(4) 0.5373(3) 0.0428(3) 0.0177(8) Uani 1 1 d . . . C12 C 0.5651(5) 0.6471(3) -0.0643(3) 0.0295(10) Uani 1 1 d . . . H12 H 0.4788 0.6861 -0.0934 0.035 Uiso 1 1 calc R . . C13 C 0.7067(5) 0.6315(3) -0.1140(3) 0.0262(9) Uani 1 1 d . . . H13 H 0.7306 0.6592 -0.1823 0.031 Uiso 1 1 calc R . . C14 C 0.6416(4) 0.7242(3) 0.3801(3) 0.0165(8) Uani 1 1 d . . . C15 C 0.7780(4) 0.6586(3) 0.3545(3) 0.0169(8) Uani 1 1 d . . . H15A H 0.8785 0.6815 0.3561 0.020 Uiso 1 1 calc R . . H15B H 0.7793 0.6657 0.2881 0.020 Uiso 1 1 calc R . . C16 C 0.7648(4) 0.5477(3) 0.4247(3) 0.0167(8) Uani 1 1 d . . . H16A H 0.6594 0.5268 0.4286 0.020 Uiso 1 1 calc R . . H16B H 0.8442 0.5069 0.3992 0.020 Uiso 1 1 calc R . . C17 C 0.7899(4) 0.5281(3) 0.5266(3) 0.0142(7) Uani 1 1 d . . . C18 C 0.7727(4) 0.3903(3) 0.6945(3) 0.0159(7) Uani 1 1 d . . . C19 C 0.8211(4) 0.4412(3) 0.7425(3) 0.0178(8) Uani 1 1 d . . . H19 H 0.8309 0.5111 0.7116 0.021 Uiso 1 1 calc R . . C20 C 0.8546(5) 0.3863(3) 0.8373(3) 0.0228(8) Uani 1 1 d . . . H20 H 0.8889 0.4193 0.8699 0.027 Uiso 1 1 calc R . . C21 C 0.8372(6) 0.2828(3) 0.8835(3) 0.0270(9) Uani 1 1 d . . . C22 C 0.7927(5) 0.2315(3) 0.8349(3) 0.0254(9) Uani 1 1 d . . . H22 H 0.7851 0.1615 0.8654 0.030 Uiso 1 1 calc R . . C23 C 0.7598(5) 0.2857(3) 0.7406(3) 0.0212(8) Uani 1 1 d . . . H23 H 0.7289 0.2520 0.7076 0.025 Uiso 1 1 calc R . . C24 C 1.1307(7) 0.1237(5) 0.9623(4) 0.0620(11) Uani 1 1 d . . . C26 C 1.3690(7) 0.0704(5) 0.8960(4) 0.0620(11) Uani 1 1 d . . . H26 H 1.4421 0.0263 0.8766 0.074 Uiso 1 1 calc R . . C27 C -0.0212(6) -0.0200(4) 0.2619(4) 0.0444(12) Uani 1 1 d . . . H27A H -0.0215 -0.0856 0.2616 0.067 Uiso 1 1 calc R . . H27B H -0.0938 0.0266 0.2204 0.067 Uiso 1 1 calc R . . H27C H -0.0548 -0.0249 0.3278 0.067 Uiso 1 1 calc R . . C28 C 0.1447(6) 0.0176(3) 0.2242(3) 0.0343(11) Uani 1 1 d . . . C29 C 0.1665(8) 0.1225(4) 0.2122(4) 0.0539(16) Uani 1 1 d . . . H29A H 0.2789 0.1343 0.1967 0.081 Uiso 1 1 calc R . . H29B H 0.1214 0.1295 0.2724 0.081 Uiso 1 1 calc R . . H29C H 0.1131 0.1710 0.1600 0.081 Uiso 1 1 calc R . . N1 N 0.3543(4) 0.1084(2) 0.4000(2) 0.0155(6) Uani 1 1 d . . . N2 N 0.8527(4) 0.4768(2) 0.1071(2) 0.0175(7) Uani 1 1 d . . . N3 N 0.8145(4) 0.5698(2) -0.0537(2) 0.0185(7) Uani 1 1 d . . . N4 N 0.7379(4) 0.4387(2) 0.5977(2) 0.0169(6) Uani 1 1 d . . . H4 H 0.6766 0.4077 0.5821 0.020 Uiso 1 1 calc R . . N5 N 0.9788(5) 0.1151(2) 1.0066(3) 0.0279(8) Uani 1 1 d . . . N6 N 1.2119(4) 0.0487(3) 0.9416(3) 0.0324(9) Uani 1 1 d . . . O1 O 0.1003(3) -0.2887(2) 0.4888(2) 0.0245(6) Uani 1 1 d . . . H1 H 0.0137 -0.3151 0.5087 0.037 Uiso 1 1 calc R . . O2 O -0.0349(3) -0.1734(2) 0.5401(2) 0.0297(7) Uani 1 1 d . . . O3 O 0.5042(3) -0.02796(19) 0.3874(2) 0.0239(6) Uani 1 1 d . . . O4 O 0.9394(4) 0.4029(2) 0.2656(2) 0.0302(7) Uani 1 1 d . . . O5 O 0.7071(4) 0.5286(2) 0.2424(2) 0.0289(7) Uani 1 1 d . . . O6 O 0.6852(3) 0.8157(2) 0.3600(2) 0.0277(7) Uani 1 1 d . . . H6B H 0.6090 0.8478 0.3784 0.042 Uiso 1 1 calc R . . O7 O 0.5061(3) 0.6974(2) 0.4143(2) 0.0267(6) Uani 1 1 d . . . O8 O 0.8560(3) 0.58767(19) 0.54298(19) 0.0192(6) Uani 1 1 d . . . O9 O 0.9473(7) 0.2781(3) 1.0310(3) 0.0821(18) Uani 1 1 d . . . O10 O 0.7183(6) 0.1750(3) 1.0677(2) 0.0690(15) Uani 1 1 d . . . O11 O 0.2558(4) -0.0351(3) 0.2038(3) 0.0513(10) Uani 1 1 d . . . S1 S 0.79596(12) 0.44596(7) 0.22330(7) 0.0198(2) Uani 1 1 d . . . S2 S 0.56258(12) 0.58512(8) 0.06164(8) 0.0263(2) Uani 1 1 d . . . S3 S 0.86939(19) 0.21405(9) 1.00641(8) 0.0439(4) Uani 1 1 d . . . S4 S 1.2482(3) 0.22550(13) 0.92631(13) 0.0832(7) Uani 1 1 d . . . C5 C 0.4630(4) 0.1862(3) 0.3535(3) 0.0142(7) Uani 1 1 d . . . C25 C 1.4022(7) 0.1627(5) 0.8831(4) 0.0620(11) Uani 1 1 d . . . H25 H 1.5018 0.1898 0.8530 0.074 Uiso 1 1 calc R . . H1A H 0.267(6) 0.125(3) 0.423(3) 0.019(11) Uiso 1 1 d . . . H3 H 0.915(6) 0.556(4) -0.074(4) 0.037(14) Uiso 1 1 d . . . H6 H 1.170(7) -0.016(5) 0.954(5) 0.064(19) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0186(19) 0.0114(17) 0.0201(19) -0.0035(15) -0.0048(15) 0.0008(14) C2 0.0149(18) 0.0146(18) 0.022(2) -0.0073(15) 0.0007(15) -0.0023(14) C3 0.0167(18) 0.0141(17) 0.0207(19) -0.0078(15) -0.0022(15) -0.0021(14) C4 0.0176(18) 0.0126(17) 0.0168(18) -0.0063(14) -0.0062(14) -0.0008(14) C6 0.0148(18) 0.0161(18) 0.0206(19) -0.0075(15) -0.0009(15) 0.0000(14) C7 0.023(2) 0.0140(17) 0.0188(19) -0.0084(15) -0.0016(15) -0.0028(15) C8 0.0204(19) 0.0163(18) 0.0125(17) -0.0043(14) -0.0027(14) -0.0057(15) C9 0.0202(19) 0.0199(19) 0.0180(19) -0.0088(16) 0.0016(15) -0.0044(15) C10 0.0207(19) 0.0148(18) 0.0196(19) -0.0081(15) -0.0007(15) -0.0026(15) C11 0.0196(19) 0.0148(18) 0.0206(19) -0.0080(15) -0.0012(15) -0.0075(15) C12 0.030(2) 0.021(2) 0.040(3) -0.0098(19) -0.016(2) 0.0015(17) C13 0.034(2) 0.020(2) 0.025(2) -0.0039(17) -0.0143(18) -0.0046(17) C14 0.0190(19) 0.0144(18) 0.0153(18) -0.0045(15) -0.0056(15) 0.0004(15) C15 0.0194(19) 0.0143(18) 0.0157(18) -0.0069(15) 0.0014(15) -0.0009(14) C16 0.0183(18) 0.0145(18) 0.0186(19) -0.0088(15) -0.0036(15) 0.0024(14) C17 0.0113(16) 0.0136(17) 0.0180(18) -0.0083(15) -0.0009(14) 0.0022(14) C18 0.0145(18) 0.0144(17) 0.0179(18) -0.0059(15) -0.0032(14) 0.0007(14) C19 0.0197(19) 0.0150(18) 0.0183(19) -0.0068(15) -0.0035(15) 0.0002(15) C20 0.030(2) 0.021(2) 0.024(2) -0.0151(17) -0.0091(17) 0.0046(16) C21 0.045(3) 0.019(2) 0.018(2) -0.0089(17) -0.0119(18) 0.0102(18) C22 0.040(2) 0.0125(18) 0.023(2) -0.0058(16) -0.0067(18) 0.0009(17) C23 0.028(2) 0.0163(19) 0.022(2) -0.0087(16) -0.0059(16) -0.0036(16) C24 0.0426(19) 0.078(3) 0.0372(17) 0.0120(18) -0.0118(15) -0.0261(18) C26 0.0426(19) 0.078(3) 0.0372(17) 0.0120(18) -0.0118(15) -0.0261(18) C27 0.045(3) 0.049(3) 0.033(3) -0.013(2) -0.005(2) 0.000(2) C28 0.053(3) 0.024(2) 0.027(2) -0.0062(19) -0.019(2) -0.005(2) C29 0.100(5) 0.025(2) 0.046(3) -0.008(2) -0.047(3) -0.002(3) N1 0.0141(16) 0.0146(15) 0.0174(16) -0.0069(13) 0.0001(13) -0.0021(13) N2 0.0198(16) 0.0164(15) 0.0152(16) -0.0054(13) -0.0006(13) -0.0047(13) N3 0.0211(18) 0.0168(16) 0.0179(16) -0.0063(13) -0.0050(13) -0.0022(13) N4 0.0202(16) 0.0147(15) 0.0186(16) -0.0068(13) -0.0073(13) -0.0040(12) N5 0.049(2) 0.0139(16) 0.0224(18) -0.0068(14) -0.0146(16) 0.0047(15) N6 0.0152(17) 0.041(2) 0.0253(19) -0.0009(17) -0.0010(14) 0.0004(16) O1 0.0207(14) 0.0178(14) 0.0365(17) -0.0159(13) 0.0076(12) -0.0085(11) O2 0.0159(14) 0.0209(14) 0.052(2) -0.0186(14) 0.0035(13) -0.0021(11) O3 0.0163(14) 0.0147(13) 0.0382(17) -0.0114(12) 0.0027(12) -0.0013(11) O4 0.0297(16) 0.0389(17) 0.0197(15) -0.0043(13) -0.0062(12) -0.0175(13) O5 0.0431(18) 0.0241(15) 0.0234(15) -0.0152(13) 0.0088(13) -0.0177(13) O6 0.0236(15) 0.0146(13) 0.0434(18) -0.0143(13) 0.0038(13) -0.0015(11) O7 0.0184(15) 0.0215(14) 0.0426(18) -0.0168(13) -0.0027(13) -0.0005(11) O8 0.0218(14) 0.0149(13) 0.0217(14) -0.0068(11) -0.0039(11) -0.0057(11) O9 0.191(6) 0.0251(19) 0.054(3) -0.0221(18) -0.080(3) 0.028(3) O10 0.089(3) 0.062(3) 0.0178(17) -0.0044(17) 0.0115(19) 0.045(2) O11 0.039(2) 0.037(2) 0.078(3) -0.025(2) -0.0043(19) -0.0060(17) S1 0.0256(5) 0.0208(5) 0.0145(5) -0.0072(4) 0.0006(4) -0.0123(4) S2 0.0202(5) 0.0241(5) 0.0351(6) -0.0139(5) -0.0014(4) -0.0013(4) S3 0.0914(11) 0.0218(6) 0.0220(6) -0.0131(5) -0.0258(6) 0.0241(6) S4 0.1119(16) 0.0612(10) 0.0617(10) 0.0215(8) -0.0465(10) -0.0670(11) C5 0.0160(18) 0.0132(17) 0.0137(17) -0.0040(14) -0.0056(14) -0.0026(14) C25 0.0426(19) 0.078(3) 0.0372(17) 0.0120(18) -0.0118(15) -0.0261(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.207(5) . ? C1 O1 1.325(4) . ? C1 C2 1.501(5) . ? C2 C3 1.519(5) . ? C3 C4 1.517(5) . ? C4 O3 1.224(5) . ? C4 N1 1.351(5) . ? C6 C7 1.387(5) . ? C6 C5 1.390(5) . ? C7 C8 1.384(5) . ? C8 C9 1.388(5) . ? C8 S1 1.771(4) . ? C9 C10 1.385(5) . ? C10 C5 1.397(5) . ? C11 N2 1.327(5) . ? C11 N3 1.337(5) . ? C11 S2 1.742(4) . ? C12 C13 1.333(6) . ? C12 S2 1.734(5) . ? C13 N3 1.382(5) . ? C14 O7 1.210(5) . ? C14 O6 1.325(4) . ? C14 C15 1.499(5) . ? C15 C16 1.517(5) . ? C16 C17 1.509(5) . ? C17 O8 1.230(4) . ? C17 N4 1.353(5) . ? C18 C19 1.388(5) . ? C18 C23 1.391(5) . ? C18 N4 1.413(5) . ? C19 C20 1.390(5) . ? C20 C21 1.382(6) . ? C21 C22 1.384(6) . ? C21 S3 1.767(4) . ? C22 C23 1.380(6) . ? C24 N5 1.327(7) . ? C24 N6 1.331(9) . ? C24 S4 1.732(6) . ? C26 C25 1.339(9) . ? C26 N6 1.387(7) . ? C27 C28 1.497(7) . ? C28 O11 1.210(6) . ? C28 C29 1.496(6) . ? N1 C5 1.408(5) . ? N2 S1 1.612(3) . ? N5 S3 1.607(3) . ? O4 S1 1.439(3) . ? O5 S1 1.438(3) . ? O9 S3 1.423(4) . ? O10 S3 1.453(5) . ? S4 C25 1.680(8) . ? 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 C1 O1 123.8(3) . . ? O2 C1 C2 124.9(3) . . ? O1 C1 C2 111.3(3) . . ? C1 C2 C3 113.2(3) . . ? C4 C3 C2 112.4(3) . . ? O3 C4 N1 123.6(3) . . ? O3 C4 C3 123.2(3) . . ? N1 C4 C3 113.2(3) . . ? C7 C6 C5 120.7(3) . . ? C8 C7 C6 119.2(3) . . ? C7 C8 C9 120.6(3) . . ? C7 C8 S1 119.0(3) . . ? C9 C8 S1 120.3(3) . . ? C10 C9 C8 120.3(3) . . ? C9 C10 C5 119.4(3) . . ? N2 C11 N3 119.9(3) . . ? N2 C11 S2 130.3(3) . . ? N3 C11 S2 109.8(3) . . ? C13 C12 S2 111.2(3) . . ? C12 C13 N3 113.2(4) . . ? O7 C14 O6 123.5(3) . . ? O7 C14 C15 123.9(3) . . ? O6 C14 C15 112.5(3) . . ? C14 C15 C16 112.0(3) . . ? C17 C16 C15 112.3(3) . . ? O8 C17 N4 122.9(3) . . ? O8 C17 C16 122.5(3) . . ? N4 C17 C16 114.6(3) . . ? C19 C18 C23 120.3(3) . . ? C19 C18 N4 123.5(3) . . ? C23 C18 N4 116.1(3) . . ? C18 C19 C20 119.0(3) . . ? C21 C20 C19 120.3(4) . . ? C20 C21 C22 120.8(4) . . ? C20 C21 S3 120.3(3) . . ? C22 C21 S3 118.9(3) . . ? C23 C22 C21 119.1(4) . . ? C22 C23 C18 120.4(4) . . ? N5 C24 N6 120.9(5) . . ? N5 C24 S4 127.3(6) . . ? N6 C24 S4 111.8(4) . . ? C25 C26 N6 111.6(7) . . ? O11 C28 C29 121.8(5) . . ? O11 C28 C27 121.0(4) . . ? C29 C28 C27 117.2(5) . . ? C4 N1 C5 129.4(3) . . ? C11 N2 S1 120.8(3) . . ? C11 N3 C13 115.0(4) . . ? C17 N4 C18 127.4(3) . . ? C24 N5 S3 120.1(4) . . ? C24 N6 C26 113.1(5) . . ? O5 S1 O4 118.90(19) . . ? O5 S1 N2 111.60(17) . . ? O4 S1 N2 104.50(17) . . ? O5 S1 C8 106.36(17) . . ? O4 S1 C8 107.09(17) . . ? N2 S1 C8 107.92(16) . . ? C12 S2 C11 90.7(2) . . ? O9 S3 O10 117.2(3) . . ? O9 S3 N5 113.1(3) . . ? O10 S3 N5 104.6(2) . . ? O9 S3 C21 107.4(2) . . ? O10 S3 C21 108.8(2) . . ? N5 S3 C21 104.95(19) . . ? C25 S4 C24 89.4(3) . . ? C6 C5 C10 119.7(3) . . ? C6 C5 N1 116.4(3) . . ? C10 C5 N1 123.9(3) . . ? C26 C25 S4 114.1(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.686 _refine_diff_density_min -0.692 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 943850' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cmr_ppb_sst_thf _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Succinylsulfathiazole tetrahydrofuran solvate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H34 N6 O11 S4' _chemical_formula_weight 782.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7032(2) _cell_length_b 14.5604(5) _cell_length_c 15.5676(5) _cell_angle_alpha 64.602(2) _cell_angle_beta 77.240(2) _cell_angle_gamma 83.635(2) _cell_volume 1737.79(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8360 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 25.95 _exptl_crystal_description Rectangular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.249 _exptl_crystal_size_mid 0.069 _exptl_crystal_size_min 0.024 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'SADABS; BRUKER, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 27707 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 26.96 _reflns_number_total 7527 _reflns_number_gt 5176 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.7065P] 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 7527 _refine_ls_number_parameters 484 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_restrained_S_all 0.882 _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 0.70603(7) 0.29865(5) 0.49880(5) 0.04399(18) Uani 1 1 d . . . S2 S 0.29036(7) 0.95423(5) 0.71654(5) 0.04192(18) Uani 1 1 d . . . S3 S 0.34096(8) 0.23914(5) 0.57834(6) 0.0519(2) Uani 1 1 d . . . S4 S 0.07357(8) 1.08622(7) 0.55303(7) 0.0596(2) Uani 1 1 d . . . C8 C 0.7219(2) 0.22579(18) 0.62059(18) 0.0359(5) Uani 1 1 d . . . C4 C 0.7116(2) -0.02974(18) 0.97619(18) 0.0345(5) Uani 1 1 d . . . C11 C 0.4237(3) 0.35521(18) 0.54143(17) 0.0365(5) Uani 1 1 d . . . C7 C 0.6862(3) 0.12363(19) 0.66634(19) 0.0405(6) Uani 1 1 d . . . H7 H 0.6532 0.0928 0.6323 0.049 Uiso 1 1 calc R . . C5 C 0.7478(2) 0.11305(18) 0.81269(17) 0.0336(5) Uani 1 1 d . . . C9 C 0.7677(3) 0.27226(19) 0.67181(19) 0.0405(6) Uani 1 1 d . . . H9 H 0.7899 0.3412 0.6417 0.049 Uiso 1 1 calc R . . C1 C 0.8497(3) -0.2292(2) 1.1140(2) 0.0435(6) Uani 1 1 d . . . C10 C 0.7803(3) 0.21689(19) 0.76675(19) 0.0395(6) Uani 1 1 d . . . H10 H 0.8107 0.2486 0.8009 0.047 Uiso 1 1 calc R . . C2 C 0.7145(3) -0.1682(2) 1.14201(19) 0.0466(6) Uani 1 1 d . . . H2A H 0.7084 -0.1796 1.2088 0.056 Uiso 1 1 calc R . . H2B H 0.6173 -0.1914 1.1379 0.056 Uiso 1 1 calc R . . C6 C 0.6990(3) 0.06709(19) 0.76150(19) 0.0396(6) Uani 1 1 d . . . H6 H 0.6751 -0.0016 0.7915 0.048 Uiso 1 1 calc R . . C3 C 0.7302(3) -0.0555(2) 1.07798(19) 0.0434(6) Uani 1 1 d . . . H3A H 0.6507 -0.0184 1.1057 0.052 Uiso 1 1 calc R . . H3B H 0.8328 -0.0338 1.0762 0.052 Uiso 1 1 calc R . . C12 C 0.1664(3) 0.3810(2) 0.6018(2) 0.0571(8) Uani 1 1 d . . . H12 H 0.0796 0.4179 0.6180 0.069 Uiso 1 1 calc R . . C13 C 0.1614(3) 0.2842(2) 0.6175(2) 0.0605(8) Uani 1 1 d . . . H13 H 0.0711 0.2453 0.6464 0.073 Uiso 1 1 calc R . . C17 C -0.1257(3) 0.50977(18) 0.91884(18) 0.0350(5) Uani 1 1 d . . . C18 C -0.0419(2) 0.68911(17) 0.85085(17) 0.0317(5) Uani 1 1 d . . . C21 C 0.1585(3) 0.85287(18) 0.76415(17) 0.0335(5) Uani 1 1 d . . . C24 C 0.2637(3) 1.03778(19) 0.53815(19) 0.0378(6) Uani 1 1 d . . . C20 C 0.2023(3) 0.76507(19) 0.75031(18) 0.0403(6) Uani 1 1 d . . . H20 H 0.2993 0.7610 0.7123 0.048 Uiso 1 1 calc R . . C23 C -0.0858(3) 0.77804(19) 0.86253(19) 0.0406(6) Uani 1 1 d . . . H23 H -0.1831 0.7826 0.9000 0.049 Uiso 1 1 calc R . . C14 C -0.4126(3) 0.29135(19) 1.0096(2) 0.0411(6) Uani 1 1 d . . . C19 C 0.1021(3) 0.68337(19) 0.79296(19) 0.0413(6) Uani 1 1 d . . . H19 H 0.1310 0.6248 0.7829 0.050 Uiso 1 1 calc R . . C22 C 0.0135(3) 0.85995(19) 0.81902(19) 0.0408(6) Uani 1 1 d . . . H22 H -0.0172 0.9197 0.8267 0.049 Uiso 1 1 calc R . . C15 C -0.2595(3) 0.34432(19) 0.9755(2) 0.0434(6) Uani 1 1 d . . . H15A H -0.2169 0.3520 0.9097 0.052 Uiso 1 1 calc R . . H15B H -0.1861 0.3020 1.0158 0.052 Uiso 1 1 calc R . . C16 C -0.2703(3) 0.44658(19) 0.9772(2) 0.0425(6) Uani 1 1 d . . . H16A H -0.2851 0.4379 1.0438 0.051 Uiso 1 1 calc R . . H16B H -0.3620 0.4829 0.9517 0.051 Uiso 1 1 calc R . . C25 C 0.2221(4) 1.1256(2) 0.3826(2) 0.0582(8) Uani 1 1 d . . . H25 H 0.2492 1.1505 0.3155 0.070 Uiso 1 1 calc R . . C26 C 0.0843(4) 1.1434(3) 0.4290(3) 0.0682(9) Uani 1 1 d . . . H26 H 0.0032 1.1818 0.3989 0.082 Uiso 1 1 calc R . . C27 C 0.2476(5) 0.4290(3) 0.3129(3) 0.0884(12) Uani 1 1 d . . . H27A H 0.1622 0.4140 0.2903 0.106 Uiso 1 1 calc R . . H27B H 0.2196 0.4052 0.3828 0.106 Uiso 1 1 calc R . . C28 C 0.3976(6) 0.3789(3) 0.2849(3) 0.0931(13) Uani 1 1 d . . . H28A H 0.3888 0.3569 0.2356 0.112 Uiso 1 1 calc R . . H28B H 0.4238 0.3205 0.3406 0.112 Uiso 1 1 calc R . . C29 C 0.5199(5) 0.4593(4) 0.2463(3) 0.0915(13) Uani 1 1 d . . . H29A H 0.6074 0.4352 0.2801 0.110 Uiso 1 1 calc R . . H29B H 0.5595 0.4791 0.1775 0.110 Uiso 1 1 calc R . . C30 C 0.4360(4) 0.5455(3) 0.2642(3) 0.0850(11) Uani 1 1 d . . . H30A H 0.4521 0.5432 0.3248 0.102 Uiso 1 1 calc R . . H30B H 0.4741 0.6097 0.2122 0.102 Uiso 1 1 calc R . . O3 O 0.6490(2) -0.08662(14) 0.95551(13) 0.0481(5) Uani 1 1 d . . . O2 O 0.9792(2) -0.19705(16) 1.07432(17) 0.0622(6) Uani 1 1 d . . . O4 O 0.6605(3) 0.23061(16) 0.46420(14) 0.0598(5) Uani 1 1 d . . . O1 O 0.8112(3) -0.32359(16) 1.13854(18) 0.0694(7) Uani 1 1 d . . . O5 O 0.8481(2) 0.35486(17) 0.44827(15) 0.0655(6) Uani 1 1 d . . . O8 O 0.00002(19) 0.47360(13) 0.89438(15) 0.0513(5) Uani 1 1 d . . . O6 O -0.4005(2) 0.20695(16) 0.99774(17) 0.0608(6) Uani 1 1 d . . . O10 O 0.2029(2) 1.03730(14) 0.73232(14) 0.0586(6) Uani 1 1 d . . . O7 O -0.5345(2) 0.32116(16) 1.04363(19) 0.0698(7) Uani 1 1 d . . . O9 O 0.4284(2) 0.91688(17) 0.75785(15) 0.0610(6) Uani 1 1 d . . . O11 O 0.2755(3) 0.5348(3) 0.2685(3) 0.1108(10) Uani 1 1 d . . . N1 N 0.7673(2) 0.06199(16) 0.90914(16) 0.0391(5) Uani 1 1 d . . . N2 N 0.5726(2) 0.38344(15) 0.50204(15) 0.0384(5) Uani 1 1 d . . . N5 N 0.3499(2) 0.98132(16) 0.60347(15) 0.0391(5) Uani 1 1 d . . . N4 N -0.1504(2) 0.60951(15) 0.89785(16) 0.0369(5) Uani 1 1 d . . . N6 N 0.3219(3) 1.06640(17) 0.44385(16) 0.0428(5) Uani 1 1 d . . . N3 N 0.3146(2) 0.42051(18) 0.55894(17) 0.0445(5) Uani 1 1 d . . . H1A H 0.909(6) -0.357(4) 1.113(3) 0.131(17) Uiso 1 1 d . . . H1 H 0.801(3) 0.101(2) 0.928(2) 0.053(8) Uiso 1 1 d . . . H6A H -0.482(5) 0.178(4) 1.016(3) 0.119(17) Uiso 1 1 d . . . H4 H -0.238(3) 0.6247(19) 0.9168(18) 0.033(7) Uiso 1 1 d . . . H3 H 0.343(4) 0.486(3) 0.546(2) 0.069(10) Uiso 1 1 d . . . H6B H 0.416(4) 1.052(2) 0.426(2) 0.061(10) 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 0.0456(3) 0.0385(4) 0.0388(4) -0.0130(3) 0.0006(3) 0.0041(3) S2 0.0491(3) 0.0384(4) 0.0379(4) -0.0177(3) 0.0047(3) -0.0183(3) S3 0.0485(4) 0.0364(4) 0.0689(5) -0.0233(4) 0.0002(3) -0.0106(3) S4 0.0369(3) 0.0707(6) 0.0815(6) -0.0447(5) -0.0061(3) 0.0026(3) C8 0.0325(11) 0.0306(13) 0.0412(14) -0.0143(11) -0.0035(9) 0.0030(9) C4 0.0306(10) 0.0309(13) 0.0433(14) -0.0198(11) -0.0036(9) 0.0056(9) C11 0.0408(12) 0.0277(13) 0.0361(13) -0.0080(11) -0.0081(10) -0.0022(10) C7 0.0474(13) 0.0336(14) 0.0446(15) -0.0204(12) -0.0086(11) -0.0001(11) C5 0.0340(11) 0.0282(13) 0.0386(14) -0.0149(11) -0.0059(9) 0.0010(9) C9 0.0403(12) 0.0261(13) 0.0496(16) -0.0122(12) -0.0043(11) -0.0034(10) C1 0.0502(14) 0.0353(15) 0.0442(15) -0.0158(12) -0.0138(12) 0.0090(11) C10 0.0414(12) 0.0315(14) 0.0495(16) -0.0192(12) -0.0096(11) -0.0040(10) C2 0.0559(15) 0.0384(15) 0.0373(15) -0.0131(12) -0.0031(12) 0.0082(12) C6 0.0498(13) 0.0251(13) 0.0453(15) -0.0154(11) -0.0102(11) -0.0005(10) C3 0.0542(14) 0.0370(15) 0.0425(15) -0.0214(12) -0.0108(12) 0.0092(12) C12 0.0388(13) 0.0524(19) 0.073(2) -0.0230(16) -0.0041(13) -0.0001(12) C13 0.0393(14) 0.054(2) 0.084(2) -0.0288(17) 0.0028(14) -0.0120(13) C17 0.0335(11) 0.0274(13) 0.0439(14) -0.0154(11) -0.0053(10) -0.0021(9) C18 0.0323(10) 0.0254(12) 0.0353(13) -0.0118(10) -0.0039(9) -0.0016(9) C21 0.0384(11) 0.0293(13) 0.0309(12) -0.0128(10) 0.0011(9) -0.0080(9) C24 0.0364(11) 0.0332(14) 0.0469(15) -0.0225(12) 0.0022(10) -0.0087(10) C20 0.0366(11) 0.0360(14) 0.0443(15) -0.0197(12) 0.0085(10) -0.0060(10) C23 0.0345(11) 0.0344(14) 0.0502(16) -0.0214(12) 0.0068(10) -0.0045(10) C14 0.0377(12) 0.0278(14) 0.0542(16) -0.0171(12) -0.0011(11) -0.0022(10) C19 0.0397(12) 0.0292(14) 0.0547(16) -0.0237(12) 0.0052(11) -0.0016(10) C22 0.0434(12) 0.0273(13) 0.0492(15) -0.0200(12) 0.0064(11) -0.0040(10) C15 0.0368(12) 0.0300(14) 0.0606(17) -0.0208(13) 0.0018(11) -0.0044(10) C16 0.0383(12) 0.0319(14) 0.0540(16) -0.0194(12) 0.0030(11) -0.0059(10) C25 0.0700(19) 0.0535(19) 0.0518(19) -0.0176(15) -0.0235(15) 0.0013(15) C26 0.0619(19) 0.068(2) 0.088(3) -0.037(2) -0.0380(18) 0.0157(16) C27 0.102(3) 0.085(3) 0.077(3) -0.028(2) -0.025(2) -0.006(2) C28 0.133(4) 0.074(3) 0.084(3) -0.041(2) -0.041(3) 0.027(3) C29 0.092(3) 0.099(3) 0.084(3) -0.048(3) -0.016(2) 0.033(3) C30 0.075(2) 0.082(3) 0.102(3) -0.043(2) -0.022(2) 0.012(2) O3 0.0580(11) 0.0389(11) 0.0472(11) -0.0149(9) -0.0085(8) -0.0173(8) O2 0.0466(11) 0.0514(13) 0.0921(17) -0.0366(12) -0.0094(10) 0.0059(9) O4 0.0898(15) 0.0501(13) 0.0434(11) -0.0258(10) -0.0135(10) 0.0108(11) O1 0.0646(13) 0.0353(12) 0.0985(18) -0.0285(12) 0.0025(12) 0.0028(10) O5 0.0466(10) 0.0636(14) 0.0571(13) -0.0088(11) 0.0133(9) -0.0017(9) O8 0.0370(9) 0.0289(10) 0.0793(14) -0.0215(10) 0.0040(9) -0.0013(7) O6 0.0484(11) 0.0430(12) 0.0943(17) -0.0429(12) 0.0175(10) -0.0175(9) O10 0.0823(14) 0.0371(11) 0.0557(12) -0.0284(10) 0.0176(10) -0.0231(10) O7 0.0357(9) 0.0515(13) 0.122(2) -0.0484(14) 0.0140(11) -0.0063(9) O9 0.0573(11) 0.0749(15) 0.0504(12) -0.0192(11) -0.0113(9) -0.0270(10) O11 0.0853(19) 0.087(2) 0.171(3) -0.067(2) -0.0275(19) 0.0171(16) N1 0.0501(12) 0.0279(12) 0.0448(13) -0.0176(10) -0.0132(9) -0.0039(9) N2 0.0387(10) 0.0278(11) 0.0414(12) -0.0091(9) -0.0047(8) 0.0000(8) N5 0.0406(10) 0.0358(12) 0.0355(12) -0.0132(10) 0.0023(9) -0.0059(9) N4 0.0281(9) 0.0270(11) 0.0524(13) -0.0175(10) 0.0016(9) -0.0027(8) N6 0.0440(12) 0.0396(13) 0.0403(13) -0.0138(10) -0.0056(10) -0.0002(10) N3 0.0398(11) 0.0328(13) 0.0567(15) -0.0158(11) -0.0073(9) -0.0002(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O5 1.435(2) . ? S1 O4 1.438(2) . ? S1 N2 1.608(2) . ? S1 C8 1.760(3) . ? S2 O9 1.432(2) . ? S2 O10 1.439(2) . ? S2 N5 1.603(2) . ? S2 C21 1.763(2) . ? S3 C13 1.714(3) . ? S3 C11 1.720(2) . ? S4 C26 1.728(4) . ? S4 C24 1.732(2) . ? C8 C7 1.383(3) . ? C8 C9 1.384(3) . ? C4 O3 1.222(3) . ? C4 N1 1.354(3) . ? C4 C3 1.506(4) . ? C11 N2 1.332(3) . ? C11 N3 1.337(3) . ? C7 C6 1.375(4) . ? C5 C6 1.390(3) . ? C5 C10 1.398(3) . ? C5 N1 1.401(3) . ? C9 C10 1.370(4) . ? C1 O2 1.197(3) . ? C1 O1 1.320(3) . ? C1 C2 1.496(4) . ? C2 C3 1.514(4) . ? C12 C13 1.328(4) . ? C12 N3 1.376(3) . ? C17 O8 1.216(3) . ? C17 N4 1.348(3) . ? C17 C16 1.514(3) . ? C18 C23 1.385(3) . ? C18 C19 1.390(3) . ? C18 N4 1.407(3) . ? C21 C22 1.379(3) . ? C21 C20 1.385(3) . ? C24 N5 1.325(3) . ? C24 N6 1.334(3) . ? C20 C19 1.383(3) . ? C23 C22 1.380(3) . ? C14 O7 1.200(3) . ? C14 O6 1.309(3) . ? C14 C15 1.489(3) . ? C15 C16 1.493(3) . ? C25 C26 1.317(4) . ? C25 N6 1.379(4) . ? C27 O11 1.415(5) . ? C27 C28 1.496(6) . ? C28 C29 1.501(6) . ? C29 C30 1.480(5) . ? C30 O11 1.407(5) . ? 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 O5 S1 O4 118.41(14) . . ? O5 S1 N2 104.67(12) . . ? O4 S1 N2 112.64(12) . . ? O5 S1 C8 108.58(12) . . ? O4 S1 C8 106.92(12) . . ? N2 S1 C8 104.79(11) . . ? O9 S2 O10 118.20(13) . . ? O9 S2 N5 104.55(12) . . ? O10 S2 N5 111.92(12) . . ? O9 S2 C21 107.86(12) . . ? O10 S2 C21 106.42(11) . . ? N5 S2 C21 107.43(11) . . ? C13 S3 C11 90.64(13) . . ? C26 S4 C24 90.93(15) . . ? C7 C8 C9 119.6(2) . . ? C7 C8 S1 121.12(19) . . ? C9 C8 S1 119.27(19) . . ? O3 C4 N1 122.2(2) . . ? O3 C4 C3 122.7(2) . . ? N1 C4 C3 115.1(2) . . ? N2 C11 N3 120.7(2) . . ? N2 C11 S3 129.19(19) . . ? N3 C11 S3 110.10(17) . . ? C6 C7 C8 120.8(2) . . ? C6 C5 C10 119.2(2) . . ? C6 C5 N1 124.2(2) . . ? C10 C5 N1 116.6(2) . . ? C10 C9 C8 120.1(2) . . ? O2 C1 O1 123.2(2) . . ? O2 C1 C2 124.3(3) . . ? O1 C1 C2 112.6(2) . . ? C9 C10 C5 120.5(2) . . ? C1 C2 C3 112.4(2) . . ? C7 C6 C5 119.7(2) . . ? C4 C3 C2 112.2(2) . . ? C13 C12 N3 112.3(3) . . ? C12 C13 S3 112.1(2) . . ? O8 C17 N4 123.8(2) . . ? O8 C17 C16 123.1(2) . . ? N4 C17 C16 113.1(2) . . ? C23 C18 C19 119.5(2) . . ? C23 C18 N4 116.7(2) . . ? C19 C18 N4 123.7(2) . . ? C22 C21 C20 120.2(2) . . ? C22 C21 S2 119.35(18) . . ? C20 C21 S2 120.43(17) . . ? N5 C24 N6 120.5(2) . . ? N5 C24 S4 130.27(19) . . ? N6 C24 S4 109.3(2) . . ? C19 C20 C21 120.1(2) . . ? C22 C23 C18 120.6(2) . . ? O7 C14 O6 122.8(2) . . ? O7 C14 C15 125.2(2) . . ? O6 C14 C15 112.0(2) . . ? C20 C19 C18 119.8(2) . . ? C21 C22 C23 119.7(2) . . ? C14 C15 C16 114.2(2) . . ? C15 C16 C17 113.0(2) . . ? C26 C25 N6 113.1(3) . . ? C25 C26 S4 111.4(2) . . ? O11 C27 C28 106.4(4) . . ? C27 C28 C29 104.8(3) . . ? C30 C29 C28 104.5(3) . . ? O11 C30 C29 106.2(3) . . ? C30 O11 C27 106.4(3) . . ? C4 N1 C5 128.4(2) . . ? C11 N2 S1 119.28(18) . . ? C24 N5 S2 121.89(17) . . ? C17 N4 C18 128.9(2) . . ? C24 N6 C25 115.4(2) . . ? C11 N3 C12 114.8(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.96 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.701 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 943851'