Reactivity study of 4-hydroxy-2<i>H</i>-chromene-2-thiones with symmetrical 1,4-acetylene dicarboxylates and methyl propiolate using ytterbium(III) triflate as catalyst: stereoselective synthesis of substituted fumarate and (<i>Z</i>) acrylate derivatives.
Sk, Eman Ali; Khan, Abu Taleb; Organic & biomolecular chemistry 23 (2025) 10336–10344; doi:10.1039/d5ob01518a

data_7160836
_publ_section_title
;
 Reactivity study of 4-hydroxy-2<i>H</i>-chromene-2-thiones with
 symmetrical 1,4-acetylene dicarboxylates and methyl propiolate using
 ytterbium(III) triflate as catalyst: stereoselective synthesis of
 substituted fumarate and (<i>Z</i>) acrylate derivatives.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10336
_journal_page_last               10344
_journal_paper_doi               10.1039/d5ob01518a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C18 H18 O6 S'
_chemical_formula_sum            'C18 H18 O6 S'
_chemical_formula_weight         362.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-10-12 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.560(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2431(5)
_cell_length_b                   7.5910(4)
_cell_length_c                   26.1848(15)
_cell_measurement_reflns_used    9289
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.80
_cell_volume                     1821.27(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            40579
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.547
_exptl_absorpt_coefficient_mu    0.208
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.322
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.322
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.3003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.1884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2709
_reflns_number_total             3178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01518a2.cif
_cod_data_source_block           1ATKES5P_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160834--7160836.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160836
_shelx_shelxl_version_number     2019/1
_shelx_res_checksum              14193