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_7159922
_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         'C26 H19 N O4'
_chemical_formula_sum            'C26 H19 N O4'
_chemical_formula_weight         409.42
_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
_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                 107.478(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5055(5)
_cell_length_b                   22.2353(8)
_cell_length_c                   8.1847(4)
_cell_measurement_reflns_used    11017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.0560
_cell_measurement_theta_min      3.9460
_cell_volume                     1997.21(16)
_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 2018/2 (Sheldrick, 2018)'
_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 0.999
_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     18.00  78.00   0.50    0.84    --   40.83-104.00 166.00  120
  2  \w    -82.00 -12.00   0.50    3.37    --  -82.50 104.00 -91.00  140
  3  \w   -153.00 -83.00   0.50    3.37    --  -82.50-104.00 166.00  140
  4  \w    105.00 174.00   0.50    3.37    --  104.00 104.00 -91.00  138
  5  \w     34.00 107.00   0.50    3.37    --  104.00-104.00 166.00  146
  6  \w   -108.00 -17.00   0.50    0.84    --  -40.83 -65.00  30.00  182
  7  \w    -24.00  35.00   0.50    0.84    --  -40.83  11.00-180.00  118
  8  \w    -78.00   4.00   0.50    0.84    --  -40.83 104.00 -91.00  164
  9  \w    -97.00 -19.00   0.50    0.84    --  -40.83 138.00   0.00  156
 10  \w    -28.00  31.00   0.50    0.84    --  -40.83  21.00-120.00  118
 11  \w    -24.00  35.00   0.50    0.84    --  -40.83  11.00  90.00  118
 12  \w    -28.00  31.00   0.50    0.84    --  -40.83  21.00 -60.00  118
 13  \w    -24.00  35.00   0.50    0.84    --  -40.83  11.00-150.00  118
 14  \w   -109.00 -28.00   0.50    0.84    --  -40.83 -32.00-120.00  162
 15  \w      8.00  35.00   0.50    0.84    --   40.83  94.00   7.68   54
 16  \w     10.00  43.00   0.50    0.84    --   40.83  89.00  53.75   66
 17  \w     12.00  43.00   0.50    0.84    --   40.83  83.00 110.08   62
 18  \w     11.00  43.00   0.50    0.84    --   40.83  86.00 -10.24   64
 19  \w     14.00  43.00   0.50    0.84    --   40.83  79.00 148.67   58
 20  \w    -31.00  28.00   0.50    0.84    --   40.83 -21.00 -90.00  118
 21  \w     11.00  43.00   0.50    0.84    --   40.83  87.00   2.43   64
 22  \w    -35.00  24.00   0.50    0.84    --   40.83 -11.00 -90.00  118
 23  \w     41.00 100.00   0.50    0.84    --   40.83-138.00 -90.00  118
 24  \w    -35.00  24.00   0.50    0.84    --   40.83 -11.00  60.00  118
 25  \w     10.00  43.00   0.50    0.84    --   40.83  89.00-155.16   66
 26  \w    -25.00  48.00   0.50    0.84    --   40.83 -43.00-180.00  146
 27  \w      9.00  42.00   0.50    0.84    --   40.83  92.00 166.37   66
 28  \w     10.00  43.00   0.50    0.84    --   40.83  88.00  30.37   66
 29  \w     22.00 109.00   0.50    0.84    --   40.83  51.00-111.84  174
 30  \w    -47.00 -15.00   0.50    3.37    --  -82.50  42.00-150.00   64
 31  \w    -47.00 -15.00   0.50    3.37    --  -82.50  42.00  60.00   64
 32  \w   -152.00 -57.00   0.50    3.37    --  -82.50 -72.00 102.23  190
 33  \w    -47.00 -15.00   0.50    3.37    --  -82.50  42.00 120.00   64
 34  \w    -47.00 -15.00   0.50    3.37    --  -82.50  42.00-180.00   64
 35  \w   -150.00 -66.00   0.50    3.37    --  -82.50 -42.00  30.00  168
 36  \w    -47.00 -15.00   0.50    3.37    --  -82.50  42.00  30.00   64
 37  \w     90.00 172.00   0.50    3.37    --  104.00  33.00 150.00  164
 38  \w     36.00  83.00   0.50    3.37    --  104.00 -68.00  60.00   94
 39  \w     36.00  68.00   0.50    3.37    --  104.00 -59.00 -90.00   64
 40  \w     36.00  68.00   0.50    3.37    --  104.00 -59.00 120.00   64
 41  \w     38.00 118.00   0.50    3.37    --  104.00-133.00  90.00  160
 42  \w     38.00 108.00   0.50    3.37    --  104.00-111.00 -30.00  140
 43  \w     38.00 118.00   0.50    3.37    --  104.00-133.00 150.00  160
 44  \w     62.00 146.00   0.50    3.37    --  104.00 178.00 120.00  168
 45  \w     87.00 171.00   0.50    3.37    --  104.00  42.00  90.00  168
 46  \w     81.00 172.00   0.50    3.37    --  104.00  64.00 -63.41  182
 47  \w     80.00 172.00   0.50    3.37    --  104.00  68.00-150.00  184
 48  \w     36.00  83.00   0.50    3.37    --  104.00 -68.00  30.00   94
 49  \w     38.00 108.00   0.50    3.37    --  104.00-111.00-150.00  140
 50  \w     36.00  68.00   0.50    3.37    --  104.00 -59.00  90.00   64
 51  \w     38.00 108.00   0.50    3.37    --  104.00-111.00 -60.00  140
 52  \w     35.00 105.00   0.50    3.37    --  104.00 -77.00-120.00  140
 53  \w    102.00 170.00   0.50    3.37    --  104.00 111.00 -60.00  136
 54  \w     82.00 172.00   0.50    3.37    --  104.00  59.00-120.00  180
 55  \w    104.00 177.00   0.50    3.37    --  104.00  93.00 -30.00  146
 56  \w     82.00 172.00   0.50    3.37    --  104.00  59.00 -90.00  180
 57  \w     34.00 135.00   0.50    3.37    --  104.00 -87.00  30.00  202
 58  \w     36.00  83.00   0.50    3.37    --  104.00 -68.00  90.00   94
 59  \w     82.00 172.00   0.50    3.37    --  104.00  59.00  30.00  180
 60  \w    104.00 177.00   0.50    3.37    --  104.00  93.00-180.00  146
 61  \w     32.00 106.00   0.50    3.37    --  104.00 -93.00  30.00  148
 62  \w    102.00 170.00   0.50    3.37    --  104.00 111.00-150.00  136
 63  \w     39.00 109.00   0.50    3.37    --  104.00-112.00   1.67  140
 64  \w     36.00  68.00   0.50    3.37    --  104.00 -59.00  60.00   64
 65  \w     77.00 173.00   0.50    3.37    --  104.00  77.00-180.00  192
 66  \w     90.00 172.00   0.50    3.37    --  104.00  33.00 -90.00  164
 67  \w     38.00 108.00   0.50    3.37    --  104.00-111.00  30.00  140
 68  \w     38.00 108.00   0.50    3.37    --  104.00-111.00 150.00  140
 69  \w     82.00 172.00   0.50    3.37    --  104.00  59.00   0.00  180
 70  \w     85.00 171.00   0.50    3.37    --  104.00  50.00 -30.00  172
 71  \w     34.00 135.00   0.50    3.37    --  104.00 -87.00  60.00  202
 72  \w     82.00 172.00   0.50    3.37    --  104.00  59.00 120.00  180
 73  \w     36.00  83.00   0.50    3.37    --  104.00 -68.00 150.00   94
 74  \w     38.00 118.00   0.50    3.37    --  104.00-133.00 -30.00  160
 75  \w     87.00 171.00   0.50    3.37    --  104.00  42.00-180.00  168
 76  \w     38.00 118.00   0.50    3.37    --  104.00-133.00 -60.00  160
 77  \w     38.00 108.00   0.50    3.37    --  104.00-111.00 -90.00  140
 78  \w     34.00 135.00   0.50    3.37    --  104.00 -87.00 120.00  202
 79  \w     48.00  92.00   0.50    3.37    --  104.00 -87.00 -30.00   88
 80  \w    128.00 159.00   0.50    3.37    --  104.00  93.00  60.00   62
 81  \w     40.00  66.00   0.50    3.37    --  104.00 -93.00 -60.00   52
 82  \w     32.00  71.00   0.50    3.37    --  104.00 -93.00   0.00   78
 83  \w    104.00 130.00   0.50    3.37    --  104.00 178.00 -60.00   52
 84  \w     32.00  90.00   0.50    3.37    --  104.00 -93.00-150.00  116
;
_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      0.0612805000
_diffrn_orient_matrix_UB_12      0.0518895000
_diffrn_orient_matrix_UB_13      0.1197316000
_diffrn_orient_matrix_UB_21      -0.0058079000
_diffrn_orient_matrix_UB_22      -0.0371688000
_diffrn_orient_matrix_UB_23      0.1561601000
_diffrn_orient_matrix_UB_31      0.1261870000
_diffrn_orient_matrix_UB_32      -0.0269079000
_diffrn_orient_matrix_UB_33      0.0150220000
_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  0.1635
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            38046
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.272
_diffrn_reflns_theta_min         3.976
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77621
_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    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1524
_refine_ls_R_factor_gt           0.0970
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2593
_refine_ls_wR_factor_ref         0.3435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1951
_reflns_number_total             3910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00438h2.cif
_cod_data_source_block           aky-d7_autored
_cod_depositor_comments
'Adding full bibliography for 7159921--7159922.cif.'
_cod_database_code               7159922
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.706
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C22(H22), C24(H24), C26(H26), C13(H13), C7(H7), C15(H15), C2(H2),
 C17(H17), C9(H9), C19(H19), C21(H21), C11(H11), C23(H23)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_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 2.919
_oxdiff_exptl_absorpt_empirical_full_min 0.439