l-Proline-catalysed synthesis of 2-aryl-2H,5H-thiopyrano[2,3-b] thiochromen-5-ones from 4-hydroxydithiocoumarins and cinnamaldehyde derivatives
Ali, Ahmad; Faraz, Simra; Khan, Abu Taleb; Organic & Biomolecular Chemistry 22 (2024) 1426–1433; doi:10.1039/D3OB02051G

data_7159767
_publ_section_title
;
 l-Proline-catalysed synthesis of 2-aryl-2H,5H-thiopyrano[2,3-b]
 thiochromen-5-ones from 4-hydroxydithiocoumarins and cinnamaldehyde
 derivatives
;
_journal_issue                   7
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1426
_journal_page_last               1433
_journal_paper_doi               10.1039/D3OB02051G
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C19 H14 O2 S2'
_chemical_formula_sum            'C19 H14 O2 S2'
_chemical_formula_weight         338.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-11-29
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-11-29 deposited with the CCDC.	2024-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                87.216(3)
_cell_angle_beta                 89.610(4)
_cell_angle_gamma                83.982(3)
_cell_formula_units_Z            4
_cell_length_a                   7.6579(10)
_cell_length_b                   13.8840(19)
_cell_length_c                   14.998(2)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      3.00
_cell_volume                     1584.0(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.00
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            41184
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.007
_diffrn_reflns_theta_min         1.958
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1332 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.9158.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0403P)^2^+0.9799P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5956
_reflns_number_total             6867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02051g2.cif
_cod_data_source_block           atk23013_0m_a
_cod_depositor_comments
;
         Adding full bibliography for 7159767.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H28 O4 S4'
_cod_original_formula_weight         676.84
_cod_original_formula_moiety         '2(C19 H14 O2 S2)'
_cod_original_formula_units_Z            2
_cod_database_code               7159767
_shelx_shelxl_version_number     2018/3
_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 Ternary CH refined with riding coordinates:
 C4(H4), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C24(H24), C25(H25), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              47335
_olex2_submission_special_instructions 'No special instructions were received'