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_7160835
_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         'C13 H9 F O4 S'
_chemical_formula_sum            'C13 H9 F O4 S'
_chemical_formula_weight         280.26
_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             2025-09-19
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-09-19 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.479(7)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   10.802(3)
_cell_length_b                   13.196(3)
_cell_length_c                   25.591(6)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.44
_cell_volume                     3647.7(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.00
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CMOS-PHOTONII-7
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            84819
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.040
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1364 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.8675.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'very faint yellow'
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       needle
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.9854
_exptl_crystal_size_mid          0.7622
_exptl_crystal_size_min          0.5345
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         6410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0545P)^2^+2.2911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4794
_reflns_number_total             6410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01518a2.cif
_cod_data_source_block           1atke5f_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160834--7160836.cif.'
_cod_original_cell_volume        3647.7(15)
_cod_database_code               7160835
_shelx_shelxl_version_number     2019/1
_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:
 C36(H36), C10(H10), C32(H32), C19(H19), C23(H23), C6(H6), C15(H15), C28(H28),
 C2(H2), C11(H11), C37(H37), C35(H35), C9(H9), C24(H24), C22(H22), C20(H20),
 C7(H7), C33(H33)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C39(H39A,H39B,H39C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              52821
_olex2_submission_special_instructions 'No special instructions were received'