#=============================================================================
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 -0.7255 0.55475 1
1 7 0 54.4163 0.79882 -2
1 7 0 54.4163 0.79882 1
2 7 0 74.7220 1.07170 -2
2 7 0 74.7220 1.07170 1
3 7 0 25.2834 0.65110 -2
3 7 0 25.2834 0.65110 1
4 7 0 123.017 1.78201 -2
4 7 0 123.017 1.78201 1
5 7 0 3.64992 0.73653 -2
5 7 0 3.64992 0.73653 1
6 7 0 2.80476 0.85781 -2
6 7 0 2.80476 0.85781 1
7 7 0 0.53235 1.21487 -2
7 7 0 0.53235 1.21487 1
8 7 0 -0.9257 1.40640 -2
8 7 0 -0.9257 1.40640 1
9 7 0 -0.5851 1.68995 -2
9 7 0 -0.5851 1.68995 1
0 8 0 1.31574 0.67559 -2
0 8 0 1.31574 0.67559 1
1 8 0 -0.3254 0.43836 -2
1 8 0 -0.3254 0.43836 1
2 8 0 311.084 3.59938 -2
2 8 0 311.084 3.59938 1
3 8 0 25.5071 0.71748 -2
3 8 0 25.5071 0.71748 1
4 8 0 7.27401 0.70464 -2
4 8 0 7.27401 0.70464 1
5 8 0 27.4010 0.96202 -2
5 8 0 27.4010 0.96202 1
6 8 0 1.18591 0.99119 -2
6 8 0 1.18591 0.99119 1
7 8 0 1.53590 1.31173 -2
7 8 0 1.53590 1.31173 1
8 8 0 -0.0517 1.47020 -2
8 8 0 -0.0517 1.47020 1
9 8 0 2.14164 1.92170 -2
9 8 0 2.14164 1.92170 1
0 9 0 0.30187 0.72465 -2
0 9 0 0.30187 0.72465 1
1 9 0 967.253 11.6909 -2
1 9 0 967.253 11.6909 1
2 9 0 30.2154 0.71392 -2
2 9 0 30.2154 0.71392 1
3 9 0 5.62404 0.61695 -2
3 9 0 5.62404 0.61695 1
4 9 0 26.2268 0.89465 -2
4 9 0 26.2268 0.89465 1
5 9 0 4.66203 0.83065 -2
5 9 0 4.66203 0.83065 1
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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