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_7160834
_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         'C22 H26 O6 S'
_chemical_formula_sum            'C22 H26 O6 S'
_chemical_formula_weight         418.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-11-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-16 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.954(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1757(6)
_cell_length_b                   7.6127(4)
_cell_length_c                   26.4230(15)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.15
_cell_volume                     2207.0(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295.00
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_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            46937
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.873
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1250 before and 0.0647 after correction.
The Ratio of minimum to maximum transmission is 0.9450.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+1.4036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3246
_reflns_number_total             3863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01518a2.cif
_cod_data_source_block           5atkes20w_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160834--7160836.cif.'
_cod_database_code               7160834
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C6(H6), C11(H11), C2(H2)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C15(H15A,H15B,
 H15C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              46958
_olex2_submission_special_instructions 'No special instructions were received'