#============================================================================= data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 16 _journal_issue 3 _journal_year 2025 _journal_page_first 275 _journal_page_last 286 #============================================================================= data_publication_text _publ_requested_journal Eur.J.Chem. _publ_contact_author_name 'Felix Odame' _publ_contact_author_address ; Department of Basic Sciences University of Health and Allied Sciences PMB 31 Ho Ghana ; _publ_contact_author_email felixessah15@gmail.com loop_ _publ_author_name _publ_author_address 'Odame, Felix' ; Department of Basic Sciences University of Health and Allied Sciences PMB 31 Ho Ghana ; 'Hosten, Eric C.' ; Department of Chemistry Nelson Mandela University P.O. Box 77000 Port Elizabeth 6031 South Africa ; 'Tshentu, Zenixole R.' ; Department of Chemistry Nelson Mandela University P.O. Box 77000 Port Elizabeth 6031 South Africa ; _publ_section_references ; Bruker (2012). APEX, APEX2, SAINT, SADABS, TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA. Farrugia, L.J. (2012). J. Appl. Cryst. 45, 849-854. Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). J. Appl. Cryst. 48, 3-10. H\"ubschle, C.B., Sheldrick, G.M., Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284. Macrae, C.F., Edgington, P.R., McCabe, P., Pidcock, E., Shields, G.P., Taylor, R., Towler, M., van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457. Sheldrick, G.M., (2015a). Acta Cryst. A71, 3-8. Sheldrick, G.M., (2015b). Acta Cryst. C71, 3-8. Spek, A.L. (2009). Acta Cryst. D65, 148-155. ; data_ja113_tw _audit_creation_date 2025-02-15 _audit_creation_method ; Olex2 1.3-beta (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _shelx_SHELXL_version_number '2019/3' _audit_contact_author_address ? _audit_contact_author_email ? _audit_contact_author_name '' _audit_contact_author_phone ? _publ_contact_author_id_orcid ? _chemical_name_common ? _chemical_name_systematic 7-Hydroxy-4-methyl-2H-chromen-2-one _chemical_formula_moiety 'C10 H7 N O5, C2 H6 O S' _chemical_formula_sum 'C12 H13 N O6 S' _chemical_formula_weight 299.29 _chemical_melting_point ? 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' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1648(7) _cell_length_b 20.229(2) _cell_length_c 9.5583(9) _cell_angle_alpha 90 _cell_angle_beta 94.975(5) _cell_angle_gamma 90 _cell_volume 1380.1(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7980 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 23.16 _cell_measurement_theta_min 2.86 _shelx_estimated_absorpt_T_max 0.953 _shelx_estimated_absorpt_T_min 0.902 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_T_max 0.745685 _exptl_absorpt_correction_T_min 0.682471 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'TWINABS V2012/1 (Bruker AXS)' _exptl_absorpt_special_details ; Additional spherical absorption correction applied with mu*r = 0.2000 Rint obtained from twin.abs ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 624 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 -1.00 0.1010 1.00 -2.00 0.00 0.1540 0.00 -1.00 -3.00 0.0860 -1.00 3.00 1.00 0.1200 1.00 -2.00 1.00 0.1720 0.00 1.00 2.00 0.1370 0.00 -1.00 -1.00 0.0600 0.00 2.00 1.00 0.1480 0.00 -3.00 -1.00 0.0470 0.00 -1.00 0.00 0.0460 0.00 1.00 0.00 0.0930 1.00 3.00 2.00 0.1630 1.00 2.00 1.00 0.1660 0.00 -2.00 1.00 0.0890 1.00 3.00 0.00 0.1520 -1.00 -3.00 0.00 0.1120 -3.00 -2.00 0.00 0.1450 -1.00 -3.00 3.00 0.1140 -3.00 1.00 0.00 0.1560 -2.00 1.00 1.00 0.1380 0.00 -1.00 3.00 0.1260 -1.00 0.00 3.00 0.1210 -1.00 2.00 3.00 0.1240 -1.00 2.00 -1.00 0.1710 _exptl_crystal_size_max 0.407 _exptl_crystal_size_mid 0.259 _exptl_crystal_size_min 0.186 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_unetI/netI 0.0326 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3431 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.321 _diffrn_reflns_theta_min 2.013 _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source ? _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2221 _reflns_number_total 3431 _reflns_special_details ; _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. Completness statistics refer to single and composite reflections containing twin component 1 only. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'APEX2 v2011.4-1 (Bruker AXS)' _computing_data_collection 'Bruker Instrument Service v2011.4.0.0' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_molecular_graphics 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2019/3 (Sheldrick, 2015b) and ShelXle (H\"ubschle, 2011)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015a)' _refine_diff_density_max 0.487 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 3431 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0590 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+0.5854P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1522 _refine_ls_wR_factor_ref 0.1783 _refine_special_details ; All non-hydrogen atoms were refined anisotropically. Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with U~iso~(H) set to 1.2 U~eq~(C). The H atoms of the non-disordered methyl groups were allowed to rotate with a fixed angle around the C---C bonds to best fit the experimental electron density (HFIX 137 in the SHELXL program (Sheldrick, 2015b)), with U~iso~ (H) set to 1.5U~eq~(C). The H atoms of the disordered methyl groups were placed in calculated positions. The H atoms of the hydroxyl groups were allowed to rotate with a fixed angle around the C---O bonds to best fit the experimental electron density (HFIX 147 in the SHELXL program (Sheldrick, 2015)) and U~iso~(H) allowed to refine freely. The solvent DMSO molecule is disordered over two orientations necessitating the use of RIGU. Refined as a 2-component twin using HKLF 5 generated with TWINABS V2012/1. ; _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.78074 0.21926 2. Rigid body (RIGU) restrains S1, O1, C1, C2 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 S2, O2, C3, C4 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 3. Same fragment restrains {S1, O1, C1, C2} sigma for 1-2: 0.02, 1-3: 0.04 as in {S2, O2, C3, C4} 4. Others Sof(S2)=Sof(O2)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C4)=Sof(H4A)=Sof(H4B)= Sof(H4C)=1-FVAR(1) Sof(S1)=Sof(O1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)= Sof(H2C)=FVAR(1) 5.a Me refined with riding coordinates: C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C) 5.b Aromatic/amide H refined with riding coordinates: C12(H12), C24(H24), C25(H25) 5.c Idealised Me refined as rotating group: C16(H16A,H16B,H16C) 5.d Idealised tetrahedral OH refined as rotating group: O23(H23) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O14 O 0.2032(3) 0.38214(8) 0.36159(17) 0.0538(5) Uani 1 1 d . . . . . O15 O 0.1630(4) 0.27460(9) 0.3765(2) 0.0883(8) Uani 1 1 d . . . . . O23 O 0.2918(3) 0.60904(10) 0.2967(2) 0.0714(6) Uani 1 1 d . . . . . H23 H 0.310223 0.643733 0.340069 0.075(10) Uiso 1 1 calc R . . . . O22A O 0.0941(4) 0.46283(14) 0.1254(2) 0.0954(8) Uani 1 1 d . . . . . O22B O 0.3769(4) 0.49498(17) 0.1255(3) 0.1174(11) Uani 1 1 d . . . . . N22 N 0.2413(4) 0.48470(11) 0.1840(2) 0.0605(6) Uani 1 1 d . . . . . C11 C 0.2084(3) 0.39331(12) 0.6532(3) 0.0484(6) Uani 1 1 d . . . . . C12 C 0.1842(4) 0.33427(13) 0.5895(3) 0.0572(7) Uani 1 1 d . . . . . H12 H 0.168605 0.297197 0.644819 0.069 Uiso 1 1 calc R U . . . C13 C 0.1814(4) 0.32579(12) 0.4420(3) 0.0596(7) Uani 1 1 d . . . . . C16 C 0.2165(5) 0.39986(15) 0.8091(3) 0.0651(7) Uani 1 1 d . . . . . H16A H 0.117528 0.428464 0.833733 0.098 Uiso 1 1 calc R U . . . H16B H 0.335162 0.418243 0.843550 0.098 Uiso 1 1 calc R U . . . H16C H 0.201822 0.357094 0.850269 0.098 Uiso 1 1 calc R U . . . C21 C 0.2247(3) 0.44282(10) 0.4232(2) 0.0421(5) Uani 1 1 d . . . . . C22 C 0.2466(3) 0.49595(11) 0.3346(2) 0.0452(5) Uani 1 1 d . . . . . C23 C 0.2721(3) 0.55982(11) 0.3869(3) 0.0490(6) Uani 1 1 d . . . . . C24 C 0.2729(3) 0.56849(12) 0.5315(3) 0.0529(6) Uani 1 1 d . . . . . H24 H 0.288187 0.610646 0.569603 0.063 Uiso 1 1 calc R U . . . C25 C 0.2517(3) 0.51567(12) 0.6181(3) 0.0490(6) Uani 1 1 d . . . . . H25 H 0.252389 0.522904 0.714196 0.059 Uiso 1 1 calc R U . . . C26 C 0.2289(3) 0.45145(11) 0.5670(2) 0.0419(5) Uani 1 1 d . . . . . S1 S 0.3716(2) 0.78651(6) 0.49060(16) 0.0721(6) Uani 0.570(3) 1 d D . P A 1 O1 O 0.347(2) 0.7153(4) 0.4691(11) 0.107(3) Uani 0.570(3) 1 d D . P A 1 C1 C 0.486(2) 0.8155(8) 0.3490(19) 0.136(7) Uani 0.570(3) 1 d D . P A 1 H1A H 0.505574 0.862259 0.358360 0.205 Uiso 0.570(3) 1 calc R U P A 1 H1B H 0.604888 0.793617 0.347648 0.205 Uiso 0.570(3) 1 calc R U P A 1 H1C H 0.410900 0.806436 0.263077 0.205 Uiso 0.570(3) 1 calc R U P A 1 C2 C 0.174(2) 0.8275(9) 0.470(2) 0.135(7) Uani 0.570(3) 1 d D . P A 1 H2A H 0.197578 0.873724 0.485338 0.203 Uiso 0.570(3) 1 calc R U P A 1 H2B H 0.116801 0.820829 0.376506 0.203 Uiso 0.570(3) 1 calc R U P A 1 H2C H 0.090721 0.811846 0.536548 0.203 Uiso 0.570(3) 1 calc R U P A 1 S2 S 0.2849(3) 0.78474(9) 0.3525(2) 0.0775(8) Uani 0.430(3) 1 d D . P A 2 O2 O 0.310(3) 0.7181(5) 0.4079(14) 0.112(5) Uani 0.430(3) 1 d D . P A 2 C3 C 0.496(2) 0.8260(10) 0.385(3) 0.114(7) Uani 0.430(3) 1 d D . P A 2 H3A H 0.482946 0.870296 0.349343 0.171 Uiso 0.430(3) 1 calc R U P A 2 H3B H 0.529690 0.827262 0.484238 0.171 Uiso 0.430(3) 1 calc R U P A 2 H3C H 0.591034 0.803329 0.339109 0.171 Uiso 0.430(3) 1 calc R U P A 2 C4 C 0.138(3) 0.8254(9) 0.442(3) 0.107(6) Uani 0.430(3) 1 d D . P A 2 H4A H 0.122705 0.869280 0.404310 0.161 Uiso 0.430(3) 1 calc R U P A 2 H4B H 0.019736 0.803087 0.434522 0.161 Uiso 0.430(3) 1 calc R U P A 2 H4C H 0.186712 0.827685 0.538338 0.161 Uiso 0.430(3) 1 calc R U P A 2 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 O14 0.0772(12) 0.0385(9) 0.0468(10) -0.0069(7) 0.0123(8) 0.0019(8) O15 0.145(2) 0.0425(11) 0.0795(16) -0.0153(10) 0.0239(14) -0.0073(12) O23 0.0920(15) 0.0461(11) 0.0779(14) 0.0123(10) 0.0180(11) -0.0056(10) O22A 0.1007(19) 0.127(2) 0.0561(14) -0.0087(13) -0.0052(12) 0.0017(16) O22B 0.116(2) 0.171(3) 0.0735(16) -0.0215(17) 0.0523(16) -0.043(2) N22 0.0793(16) 0.0551(13) 0.0485(13) -0.0004(10) 0.0135(12) 0.0028(12) C11 0.0488(13) 0.0493(13) 0.0480(14) 0.0044(10) 0.0086(10) 0.0039(10) C12 0.0750(17) 0.0411(13) 0.0569(16) 0.0061(11) 0.0132(13) 0.0020(12) C13 0.0795(18) 0.0385(13) 0.0622(17) -0.0036(12) 0.0136(14) 0.0015(12) C16 0.087(2) 0.0642(17) 0.0448(15) 0.0052(12) 0.0092(13) 0.0008(15) C21 0.0424(11) 0.0367(11) 0.0476(13) -0.0039(9) 0.0070(9) 0.0044(9) C22 0.0466(12) 0.0450(12) 0.0449(13) -0.0011(10) 0.0097(10) 0.0029(10) C23 0.0464(13) 0.0404(12) 0.0611(16) 0.0042(11) 0.0098(11) 0.0000(10) C24 0.0546(14) 0.0397(12) 0.0646(17) -0.0115(11) 0.0068(12) -0.0037(10) C25 0.0528(13) 0.0479(13) 0.0463(13) -0.0101(11) 0.0043(10) -0.0013(11) C26 0.0397(11) 0.0422(11) 0.0442(12) -0.0032(9) 0.0057(9) 0.0019(9) S1 0.0977(12) 0.0425(7) 0.0768(11) 0.0051(6) 0.0120(8) -0.0010(6) O1 0.170(7) 0.041(3) 0.112(7) 0.001(3) 0.028(7) -0.013(3) C1 0.172(13) 0.105(10) 0.146(11) 0.055(9) 0.093(10) 0.031(8) C2 0.157(14) 0.124(10) 0.134(11) -0.025(8) 0.064(12) 0.010(9) S2 0.0976(16) 0.0604(12) 0.0751(15) -0.0120(9) 0.0113(10) -0.0062(10) O2 0.179(12) 0.042(4) 0.120(11) -0.013(5) 0.049(10) -0.013(4) C3 0.076(7) 0.066(7) 0.196(19) 0.000(9) -0.009(8) -0.021(6) C4 0.079(6) 0.072(8) 0.167(17) 0.008(8) -0.006(7) 0.000(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 O14 C13 1.391(3) . ? O14 C21 1.365(3) . ? O15 C13 1.211(3) . ? O23 H23 0.8200 . ? O23 C23 1.333(3) . ? O22A N22 1.233(3) . ? O22B N22 1.180(3) . ? N22 C22 1.454(3) . ? C11 C12 1.345(4) . ? C11 C16 1.492(4) . ? C11 C26 1.450(3) . ? C12 H12 0.9300 . ? C12 C13 1.419(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C21 C22 1.386(3) . ? C21 C26 1.383(3) . ? C22 C23 1.392(3) . ? C23 C24 1.392(4) . ? C24 H24 0.9300 . ? C24 C25 1.368(4) . ? C25 H25 0.9300 . ? C25 C26 1.392(3) . ? S1 O1 1.463(8) . ? S1 C1 1.744(11) . ? S1 C2 1.640(13) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? S2 O2 1.453(10) . ? S2 C3 1.729(12) . ? S2 C4 1.630(15) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 O14 C13 120.84(19) . . ? C23 O23 H23 109.5 . . ? O22A N22 C22 117.0(2) . . ? O22B N22 O22A 123.6(3) . . ? O22B N22 C22 119.3(3) . . ? C12 C11 C16 121.6(2) . . ? C12 C11 C26 118.6(2) . . ? C26 C11 C16 119.9(2) . . ? C11 C12 H12 118.4 . . ? C11 C12 C13 123.2(2) . . ? C13 C12 H12 118.4 . . ? O14 C13 C12 117.2(2) . . ? O15 C13 O14 115.3(2) . . ? O15 C13 C12 127.5(3) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O14 C21 C22 116.6(2) . . ? O14 C21 C26 122.3(2) . . ? C26 C21 C22 121.0(2) . . ? C21 C22 N22 119.3(2) . . ? C21 C22 C23 121.2(2) . . ? C23 C22 N22 119.5(2) . . ? O23 C23 C22 118.6(2) . . ? O23 C23 C24 123.8(2) . . ? C22 C23 C24 117.6(2) . . ? C23 C24 H24 119.6 . . ? C25 C24 C23 120.7(2) . . ? C25 C24 H24 119.6 . . ? C24 C25 H25 118.9 . . ? C24 C25 C26 122.2(2) . . ? C26 C25 H25 118.9 . . ? C21 C26 C11 117.9(2) . . ? C21 C26 C25 117.2(2) . . ? C25 C26 C11 124.9(2) . . ? O1 S1 C1 106.3(7) . . ? O1 S1 C2 112.9(9) . . ? C2 S1 C1 101.4(9) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2B 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O2 S2 C3 107.7(10) . . ? O2 S2 C4 110.1(10) . . ? C4 S2 C3 104.8(11) . . ? S2 C3 H3A 109.5 . . ? S2 C3 H3B 109.5 . . ? S2 C3 H3C 109.5 . . ? H3A C3 H3B 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? S2 C4 H4A 109.5 . . ? S2 C4 H4B 109.5 . . ? S2 C4 H4C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O23 H23 O1 0.82 1.91 2.717(9) 170 . yes O23 H23 S2 0.82 2.86 3.595(3) 150 . yes O23 H23 O2 0.82 1.64 2.448(12) 169 . yes C24 H24 O1 0.93 2.38 3.084(9) 133 . yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O14 C21 C22 N22 1.4(3) . . . . ? O14 C21 C22 C23 -179.1(2) . . . . ? O14 C21 C26 C11 -0.4(3) . . . . ? O14 C21 C26 C25 180.0(2) . . . . ? O23 C23 C24 C25 179.9(2) . . . . ? O22A N22 C22 C21 62.4(3) . . . . ? O22A N22 C22 C23 -117.1(3) . . . . ? O22B N22 C22 C21 -115.6(3) . . . . ? O22B N22 C22 C23 64.9(4) . . . . ? N22 C22 C23 O23 -0.3(3) . . . . ? N22 C22 C23 C24 178.9(2) . . . . ? C11 C12 C13 O14 -0.6(4) . . . . ? C11 C12 C13 O15 178.9(3) . . . . ? C12 C11 C26 C21 -0.8(3) . . . . ? C12 C11 C26 C25 178.9(2) . . . . ? C13 O14 C21 C22 179.6(2) . . . . ? C13 O14 C21 C26 1.0(3) . . . . ? C16 C11 C12 C13 -178.1(3) . . . . ? C16 C11 C26 C21 178.6(2) . . . . ? C16 C11 C26 C25 -1.7(4) . . . . ? C21 O14 C13 O15 179.8(2) . . . . ? C21 O14 C13 C12 -0.6(4) . . . . ? C21 C22 C23 O23 -179.8(2) . . . . ? C21 C22 C23 C24 -0.6(3) . . . . ? C22 C21 C26 C11 -178.9(2) . . . . ? C22 C21 C26 C25 1.4(3) . . . . ? C22 C23 C24 C25 0.8(4) . . . . ? C23 C24 C25 C26 0.2(4) . . . . ? C24 C25 C26 C11 179.1(2) . . . . ? C24 C25 C26 C21 -1.3(4) . . . . ? C26 C11 C12 C13 1.3(4) . . . . ? C26 C21 C22 N22 180.0(2) . . . . ? C26 C21 C22 C23 -0.5(3) . . . . ? _shelx_res_file ; TITL shelxt_a.res in P2(1)/c New: P21/c ja113_tw.res created by SHELXL-2019/3 at 12:25:37 on 23-Jan-2025 CELL 0.71073 7.1648 20.2290 9.5583 90.000 94.975 90.000 ZERR 4 0.0007 0.0020 0.0009 0.000 0.005 0.000 LATT 1 SYMM - X , 0.50000 + Y , 0.50000 - Z SFAC C H N O S UNIT 48 52 4 24 4 HTAB O23 S2 HTAB O23 O1 HTAB O23 O2 HTAB C24 O1 ACTA BOND $H CONF FMAP 2 HTAB L.S. 20 LIST 4 MERG 0 PLAN -20 SIZE 0.186 0.259 0.407 TEMP 23.000 RIGU S1 O1 C1 C2 RIGU S2 O2 C3 C4 REM EXTI 0.000000 REM WGHT 0.074400 0.583600 REM WGHT 0.074300 0.584600 REM WGHT 0.074200 0.585300 REM WGHT 0.074400 0.583400 REM WGHT 0.074300 0.584600 WGHT 0.074200 0.585400 BASF 0.21926 FVAR 0.87617 0.56954 O14 4 0.203205 0.382137 0.361588 11.00000 0.07722 0.03852 = 0.04677 -0.00691 0.01227 0.00189 O15 4 0.162967 0.274603 0.376456 11.00000 0.14527 0.04246 = 0.07951 -0.01530 0.02388 -0.00727 O23 4 0.291768 0.609044 0.296676 11.00000 0.09195 0.04611 = 0.07793 0.01228 0.01805 -0.00560 AFIX 147 H23 2 0.310223 0.643733 0.340069 11.00000 0.07504 AFIX 0 O22A 4 0.094063 0.462831 0.125371 11.00000 0.10070 0.12741 = 0.05609 -0.00867 -0.00517 0.00174 O22B 4 0.376854 0.494982 0.125477 11.00000 0.11575 0.17068 = 0.07350 -0.02149 0.05229 -0.04316 N22 3 0.241345 0.484698 0.184039 11.00000 0.07933 0.05509 = 0.04850 -0.00039 0.01352 0.00281 C11 1 0.208436 0.393309 0.653193 11.00000 0.04885 0.04929 = 0.04796 0.00445 0.00859 0.00389 C12 1 0.184235 0.334268 0.589486 11.00000 0.07501 0.04108 = 0.05689 0.00611 0.01319 0.00201 AFIX 43 H12 2 0.168605 0.297197 0.644819 11.00000 -1.20000 AFIX 0 C13 1 0.181393 0.325794 0.441954 11.00000 0.07949 0.03848 = 0.06223 -0.00356 0.01355 0.00153 C16 1 0.216451 0.399862 0.809084 11.00000 0.08681 0.06423 = 0.04483 0.00522 0.00921 0.00082 AFIX 137 H16A 2 0.117528 0.428464 0.833733 11.00000 -1.50000 H16B 2 0.335162 0.418243 0.843550 11.00000 -1.50000 H16C 2 0.201822 0.357094 0.850269 11.00000 -1.50000 AFIX 0 C21 1 0.224690 0.442821 0.423220 11.00000 0.04243 0.03670 = 0.04764 -0.00388 0.00703 0.00435 C22 1 0.246578 0.495951 0.334597 11.00000 0.04658 0.04503 = 0.04486 -0.00108 0.00973 0.00286 C23 1 0.272054 0.559818 0.386948 11.00000 0.04643 0.04035 = 0.06108 0.00418 0.00978 0.00001 C24 1 0.272949 0.568493 0.531487 11.00000 0.05464 0.03969 = 0.06463 -0.01151 0.00683 -0.00371 AFIX 43 H24 2 0.288187 0.610646 0.569603 11.00000 -1.20000 AFIX 0 C25 1 0.251652 0.515672 0.618064 11.00000 0.05283 0.04788 = 0.04630 -0.01011 0.00429 -0.00126 AFIX 43 H25 2 0.252389 0.522904 0.714196 11.00000 -1.20000 AFIX 0 C26 1 0.228911 0.451448 0.567030 11.00000 0.03972 0.04220 = 0.04417 -0.00318 0.00567 0.00191 PART 1 21.00000 S1 5 0.371606 0.786510 0.490604 21.00000 0.09772 0.04252 = 0.07681 0.00508 0.01197 -0.00104 O1 4 0.347063 0.715311 0.469089 21.00000 0.17027 0.04144 = 0.11195 0.00113 0.02840 -0.01323 C1 1 0.486106 0.815458 0.349014 21.00000 0.17168 0.10541 = 0.14581 0.05477 0.09255 0.03057 AFIX 33 H1A 2 0.505574 0.862259 0.358360 21.00000 -1.50000 H1B 2 0.604888 0.793617 0.347648 21.00000 -1.50000 H1C 2 0.410900 0.806436 0.263077 21.00000 -1.50000 AFIX 0 C2 1 0.173667 0.827471 0.470127 21.00000 0.15690 0.12413 = 0.13411 -0.02541 0.06404 0.01023 AFIX 33 H2A 2 0.197578 0.873724 0.485338 21.00000 -1.50000 H2B 2 0.116801 0.820829 0.376506 21.00000 -1.50000 H2C 2 0.090721 0.811846 0.536548 21.00000 -1.50000 AFIX 0 PART 2 -21.00000 SAME S1 O1 C1 C2 S2 5 0.284935 0.784739 0.352550 -21.00000 0.09756 0.06040 = 0.07511 -0.01199 0.01135 -0.00615 O2 4 0.310167 0.718124 0.407866 -21.00000 0.17932 0.04190 = 0.12017 -0.01333 0.04917 -0.01284 C3 1 0.495568 0.825993 0.384907 -21.00000 0.07626 0.06649 = 0.19590 0.00026 -0.00861 -0.02054 AFIX 33 H3A 2 0.482946 0.870296 0.349343 -21.00000 -1.50000 H3B 2 0.529690 0.827262 0.484238 -21.00000 -1.50000 H3C 2 0.591034 0.803329 0.339109 -21.00000 -1.50000 AFIX 0 C4 1 0.138477 0.825372 0.441575 -21.00000 0.07910 0.07249 = 0.16745 0.00775 -0.00644 0.00033 AFIX 33 H4A 2 0.122705 0.869280 0.404310 -21.00000 -1.50000 H4B 2 0.019736 0.803087 0.434522 -21.00000 -1.50000 H4C 2 0.186712 0.827685 0.538338 -21.00000 -1.50000 PART 0 REM REM ja113_tw.hkl REM AFIX 0 HKLF 5 REM shelxt_a.res in P2(1)/c New: P21/c REM wR2 = 0.1783, GooF = S = 1.044, Restrained GooF = 1.041 for all data REM R1 = 0.0590 for 2221 Fo > 4sig(Fo) and 0.0976 for all 3431 data REM 222 parameters refined using 36 restraints END WGHT 0.0744 0.5833 REM Instructions for potential hydrogen bonds HTAB O23 O1 HTAB O23 S2 HTAB O23 O2 EQIV $1 x, -y+1/2, z+1/2 HTAB C12 O15_$1 HTAB C24 O1 EQIV $2 -x, y+1/2, -z+1/2 HTAB C4 O22A_$2 REM Highest difference peak 0.487, deepest hole -0.268, 1-sigma level 0.045 Q1 1 0.1612 0.5130 0.0997 11.00000 0.05 0.49 Q2 1 0.3991 0.4444 0.1551 11.00000 0.05 0.33 Q3 1 0.4356 0.7879 0.4133 11.00000 0.05 0.27 Q4 1 0.2259 0.5237 0.3629 11.00000 0.05 0.25 Q5 1 0.2203 0.4704 0.3772 11.00000 0.05 0.24 Q6 1 0.2240 0.4462 0.5028 11.00000 0.05 0.23 Q7 1 0.2416 0.7794 0.4757 11.00000 0.05 0.23 Q8 1 0.2261 0.4219 0.6175 11.00000 0.05 0.21 Q9 1 0.2868 0.7576 0.4456 11.00000 0.05 0.21 Q10 1 0.2911 0.4825 0.5799 11.00000 0.05 0.19 Q11 1 0.2081 0.4177 0.4042 11.00000 0.05 0.18 Q12 1 0.3963 0.7109 0.4795 11.00000 0.05 0.17 Q13 1 0.4460 0.5240 0.1737 11.00000 0.05 0.17 Q14 1 0.1504 0.3016 0.4134 11.00000 0.05 0.16 Q15 1 0.5022 0.7895 0.2548 11.00000 0.05 0.16 Q16 1 0.2204 0.7105 0.4740 11.00000 0.05 0.16 Q17 1 0.2010 0.4799 0.5880 11.00000 0.05 0.15 Q18 1 0.2316 0.7264 0.3135 11.00000 0.05 0.15 Q19 1 0.2246 0.4998 0.2863 11.00000 0.05 0.15 Q20 1 0.4075 0.8307 0.5695 11.00000 0.05 0.14 ; _shelx_res_checksum 1744 _shelx_hkl_file ; 1 0 0 43.0574 0.71693 -2 1 0 0 43.0574 0.71693 1 3 0 0 925.156 12.8620 -2 3 0 0 925.156 12.8620 1 4 0 0 1328.43 20.9750 -2 4 0 0 1328.43 20.9750 1 5 0 0 191.856 3.65614 -2 5 0 0 191.856 3.65614 1 6 0 0 179.115 3.57713 -2 6 0 0 179.115 3.57713 1 7 0 0 44.2857 2.12783 -2 7 0 0 44.2857 2.12783 1 8 0 0 28.0309 2.54064 -2 8 0 0 28.0309 2.54064 1 9 0 0 -3.0254 2.12915 -2 9 0 0 -3.0254 2.12915 1 0 1 0 0.00501 0.02400 -2 0 1 0 0.00501 0.02400 1 1 1 0 17.0771 0.32388 -2 1 1 0 17.0771 0.32388 1 2 1 0 9999.99 94.9708 -2 2 1 0 9999.99 94.9708 1 3 1 0 127.948 1.44813 -2 3 1 0 127.948 1.44813 1 4 1 0 2049.38 23.6376 -2 4 1 0 2049.38 23.6376 1 5 1 0 -1.0203 0.68334 -2 5 1 0 -1.0203 0.68334 1 6 1 0 157.012 2.29985 -2 6 1 0 157.012 2.29985 1 7 1 0 28.6588 1.36409 -2 7 1 0 28.6588 1.36409 1 8 1 0 24.6540 1.79100 -2 8 1 0 24.6540 1.79100 1 9 1 0 -0.0989 1.78211 -2 9 1 0 -0.0989 1.78211 1 0 2 0 1445.76 22.8052 -2 0 2 0 1445.76 22.8052 1 1 2 0 460.089 4.65933 -2 1 2 0 460.089 4.65933 1 2 2 0 3399.41 33.2097 -2 2 2 0 3399.41 33.2097 1 3 2 0 25.1660 0.56290 -2 3 2 0 25.1660 0.56290 1 4 2 0 1509.94 16.8365 -2 4 2 0 1509.94 16.8365 1 5 2 0 -0.4864 0.67705 -2 5 2 0 -0.4864 0.67705 1 6 2 0 492.739 6.17710 -2 6 2 0 492.739 6.17710 1 7 2 0 15.0078 1.29813 -2 7 2 0 15.0078 1.29813 1 8 2 0 29.7194 1.76165 -2 8 2 0 29.7194 1.76165 1 9 2 0 8.95428 1.84292 -2 9 2 0 8.95428 1.84292 1 0 3 0 0.12393 0.30204 -2 0 3 0 0.12393 0.30204 1 1 3 0 4045.93 40.7170 -2 1 3 0 4045.93 40.7170 1 2 3 0 24.8047 0.52232 -2 2 3 0 24.8047 0.52232 1 3 3 0 -0.2493 0.48821 -2 3 3 0 -0.2493 0.48821 1 4 3 0 413.745 4.75828 -2 4 3 0 413.745 4.75828 1 5 3 0 2.91617 0.70172 -2 5 3 0 2.91617 0.70172 1 6 3 0 384.468 4.91324 -2 6 3 0 384.468 4.91324 1 7 3 0 3.18919 1.15570 -2 7 3 0 3.18919 1.15570 1 8 3 0 63.3906 2.21668 -2 8 3 0 63.3906 2.21668 1 9 3 0 0.43026 1.67609 -2 9 3 0 0.43026 1.67609 1 0 4 0 2748.98 40.4720 -2 0 4 0 2748.98 40.4720 1 1 4 0 504.427 5.12150 -2 1 4 0 504.427 5.12150 1 2 4 0 21.4119 0.50587 -2 2 4 0 21.4119 0.50587 1 3 4 0 1045.62 10.9053 -2 3 4 0 1045.62 10.9053 1 4 4 0 59.5192 1.01014 -2 4 4 0 59.5192 1.01014 1 5 4 0 27.9356 0.87064 -2 5 4 0 27.9356 0.87064 1 6 4 0 150.158 2.21985 -2 6 4 0 150.158 2.21985 1 7 4 0 2.44564 1.15370 -2 7 4 0 2.44564 1.15370 1 8 4 0 57.0151 2.14344 -2 8 4 0 57.0151 2.14344 1 9 4 0 -0.7200 1.70901 -2 9 4 0 -0.7200 1.70901 1 0 5 0 1.06141 0.49224 -2 0 5 0 1.06141 0.49224 1 1 5 0 142.537 1.59761 -2 1 5 0 142.537 1.59761 1 2 5 0 1094.08 10.7235 -2 2 5 0 1094.08 10.7235 1 3 5 0 352.410 3.90632 -2 3 5 0 352.410 3.90632 1 4 5 0 25.6417 0.76030 -2 4 5 0 25.6417 0.76030 1 5 5 0 8.82547 0.73897 -2 5 5 0 8.82547 0.73897 1 6 5 0 10.1550 0.86822 -2 6 5 0 10.1550 0.86822 1 7 5 0 9.53629 1.21440 -2 7 5 0 9.53629 1.21440 1 8 5 0 37.2261 1.87677 -2 8 5 0 37.2261 1.87677 1 9 5 0 2.51601 1.73894 -2 9 5 0 2.51601 1.73894 1 0 6 0 291.796 4.41993 -2 0 6 0 291.796 4.41993 1 1 6 0 2.99545 0.40905 -2 1 6 0 2.99545 0.40905 1 2 6 0 386.627 3.98795 -2 2 6 0 386.627 3.98795 1 3 6 0 354.467 4.07333 -2 3 6 0 354.467 4.07333 1 4 6 0 33.9354 0.85772 -2 4 6 0 33.9354 0.85772 1 5 6 0 13.8596 0.79627 -2 5 6 0 13.8596 0.79627 1 6 6 0 1.90391 0.81387 -2 6 6 0 1.90391 0.81387 1 7 6 0 -0.3795 1.11867 -2 7 6 0 -0.3795 1.11867 1 8 6 0 3.56293 1.46747 -2 8 6 0 3.56293 1.46747 1 9 6 0 2.08946 1.73804 -2 9 6 0 2.08946 1.73804 1 0 7 0 -0.7255 0.55475 -2 0 7 0 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1.79809 1 -1 8 12 -0.2665 1.60856 1 0 8 12 -0.9634 2.86489 1 -1 9 12 -1.0728 1.67706 1 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 22039 _olex2_submission_special_instructions 'No special instructions were received' loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.78074 2 0.21926