PIDA-promoted metal-free [3 + 2] heteroannulation of β-ketothioamides with 4-hydroxy coumarins: chemo-/regioselective access to furo[3,2-<i>c</i>]chromen-4-ones at room temperature.
Kumar Yadav, Anup; Yadav, Dhananjay; Kumar, Vipin; Ray, Subhasish; Singh, Maya Shankar; Organic & biomolecular chemistry 22 (2024) 4326–4331; doi:10.1039/d4ob00438h

data_7159921
_publ_section_title
;
 PIDA-promoted metal-free [3 + 2] heteroannulation of
 &#x3b2;-ketothioamides with 4-hydroxy coumarins: chemo-/regioselective
 access to furo[3,2-<i>c</i>]chromen-4-ones at room temperature.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4326
_journal_page_last               4331
_journal_paper_doi               10.1039/d4ob00438h
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C24 H15 N O4'
_chemical_formula_sum            'C24 H15 N O4'
_chemical_formula_weight         381.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-02 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4669(3)
_cell_length_b                   8.12770(10)
_cell_length_c                   21.7889(4)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.6510
_cell_measurement_theta_min      4.0460
_cell_volume                     3624.56(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -73.00   0.00   0.50    1.74    --  -40.83 104.00 -67.00  146
  2  \w    -80.00 -55.00   0.50    1.74    --  -40.83 136.00   3.00   50
  3  \w    -27.00  23.00   0.50    1.74    --  -40.83  20.00 142.00  100
  4  \w   -113.00 -30.00   0.50    1.74    --  -40.83 -20.00 -23.00  166
  5  \w      1.00  26.00   0.50    1.74    --   40.83 -20.00 -23.00   50
  6  \w     41.00  67.00   0.50    1.74    --   40.83-104.00-168.00   52
  7  \w     57.00 102.00   0.50    1.74    --   40.83  20.00 142.00   90
  8  \w     46.00  95.00   0.50    1.74    --   40.83-133.00 117.00   98
  9  \w    -65.00 -30.00   0.50    1.74    --  -82.50 104.00 -67.00   70
 10  \w   -122.00 -96.00   0.50    1.74    --  -82.50 -20.00 -23.00   52
 11  \w   -148.00 -70.00   0.50    1.74    --  -82.50-136.00 -60.00  156
 12  \w   -130.00-104.00   0.50    1.74    --  -82.50-104.00-168.00   52
 13  \w     88.00 116.00   0.50    1.74    --  104.00-136.00 -60.00   56
 14  \w    106.00 131.00   0.50    1.74    --  104.00  20.00 142.00   50
 15  \w    105.00 130.00   0.50    1.74    --  104.00 133.00-174.00   50
 16  \w     46.00  71.00   0.50    1.74    --  104.00-104.00-168.00   50
 17  \w     78.00 103.00   0.50    1.74    --  104.00-133.00 117.00   50
 18  \w    120.00 145.00   0.50    1.74    --  104.00 136.00   3.00   50
 19  \w    116.00 142.00   0.50    1.74    --  104.00 104.00 -67.00   52
 20  \w   -107.00 -14.00   0.50    1.74    --  -40.83 -77.00 -60.00  186
 21  \w     -6.00  19.00   0.50    1.74    --  -40.83  32.00 -60.00   50
 22  \w     -5.00  20.00   0.50    1.74    --   40.83 -11.00 120.00   50
 23  \w    -46.00 -15.00   0.50    1.74    --  -82.50  42.00 -90.00   62
 24  \w    -57.00 -21.00   0.50    1.74    --  -82.50  50.00-180.00   72
 25  \w     38.00  68.00   0.50    1.74    --  104.00 -59.00   0.00   60
 26  \w     36.00  65.00   0.50    1.74    --  104.00 -59.00 -60.00   58
 27  \w     36.00  64.00   0.50    1.74    --  104.00 -59.00-120.00   56
 28  \w     53.00  79.00   0.50    1.74    --  104.00-111.00 150.00   52
 29  \w     36.00  83.00   0.50    1.74    --  104.00 -68.00-180.00   94
 30  \w     52.00 103.00   0.50    1.74    --  104.00-111.00 -30.00  102
 31  \w     46.00  71.00   0.50    1.74    --  104.00 -93.00 120.00   50
 32  \w     36.00  61.00   0.50    1.74    --  104.00 -68.00 -90.00   50
 33  \w     90.00 115.00   0.50    1.74    --  104.00  33.00-180.00   50
 34  \w     36.00  67.00   0.50    1.74    --  104.00 -59.00  90.00   62
 35  \w     88.00 117.00   0.50    1.74    --  104.00-133.00 -90.00   58
 36  \w     53.00  78.00   0.50    1.74    --  104.00-133.00 -90.00   50
 37  \w    105.00 161.00   0.50    1.74    --  104.00  93.00 -90.00  112
 38  \w     38.00  66.00   0.50    1.74    --  104.00-133.00  90.00   56
 39  \w     79.00 105.00   0.50    1.74    --  104.00-133.00  90.00   52
 40  \w     60.00 108.00   0.50    1.74    --  104.00-111.00 120.00   96
 41  \w     37.00  77.00   0.50    1.74    --  104.00 -68.00 150.00   80
 42  \w     53.00  79.00   0.50    1.74    --  104.00 -68.00-150.00   52
 43  \w     48.00  73.00   0.50    1.74    --  104.00 -93.00-120.00   50
 44  \w    125.00 172.00   0.50    1.74    --  104.00  33.00-180.00   94
 45  \w     80.00 105.00   0.50    1.74    --  104.00 -93.00 120.00   50
 46  \w     79.00 141.00   0.50    1.74    --  104.00  17.00  30.00  124
 47  \w     89.00 138.00   0.50    1.74    --  104.00 133.00-180.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0344018000
_diffrn_orient_matrix_UB_12      -0.0255982000
_diffrn_orient_matrix_UB_13      -0.0621407000
_diffrn_orient_matrix_UB_21      -0.0638851000
_diffrn_orient_matrix_UB_22      -0.0436300000
_diffrn_orient_matrix_UB_23      0.0337126000
_diffrn_orient_matrix_UB_31      -0.0200693000
_diffrn_orient_matrix_UB_32      0.1826497000
_diffrn_orient_matrix_UB_33      -0.0006740000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21846
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.047
_diffrn_reflns_theta_min         4.058
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0662P)^2^+0.2566P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2701
_reflns_number_total             3536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00438h2.cif
_cod_data_source_block           aky-45_autored
_cod_depositor_comments
'Adding full bibliography for 7159921--7159922.cif.'
_cod_database_code               7159921
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.859
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C20(H20), C24(H24), C3(H3), C13(H13), C7(H7), C15(H15), C2(H2),
 C17(H17), C9(H9), C19(H19), C5(H5), C21(H21), C11(H11), C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.794