A redox active organodiselenide as an efficacious catalyst for the synthesis of oxygen-containing heterocyclic compounds
Rahman, Noimur; Kushwah, Nisha; Priyadarsini, K. Indira; New Journal of Chemistry 47 (2023) 15686–15693; doi:10.1039/D3NJ01423A

data_7062620
_publ_section_title
;
 A redox active organodiselenide as an efficacious catalyst for the
 synthesis of oxygen-containing heterocyclic compounds
;
_journal_issue                   33
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15686
_journal_page_last               15693
_journal_paper_doi               10.1039/D3NJ01423A
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-03-17 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.6360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.84440(10)
_cell_length_b                   6.53500(10)
_cell_length_c                   16.25570(10)
_cell_measurement_reflns_used    36083
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      76.9090
_cell_measurement_theta_min      2.7730
_cell_volume                     1664.08(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Ortep 3 for windows'
_computing_publication_material  'WinGX 2021.3'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_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     27.00  53.00   0.50    0.19    --   48.17  77.00   0.00   52
  2  \w     34.00  60.00   0.50    0.19    --   58.00  79.00   9.12   52
  3  \w     42.00  86.00   0.50    0.19    --   62.00  74.00 -22.08   88
  4  \w     42.00  68.00   0.50    0.19    --   66.00  79.00 -94.80   52
  5  \w     38.00  69.00   0.50    0.19    --   58.00  70.00 -34.12   62
  6  \w     51.00  77.00   0.50    0.19    --   74.00  78.00 -33.36   52
  7  \w    105.00 156.00   0.50    0.78    --  107.39  94.00 -64.00  102
  8  \w    147.00 178.00   0.50    0.78    --  107.39  77.00   0.00   62
  9  \w    143.00 177.00   0.50    0.78    --  107.39  37.00  60.00   68
 10  \w    108.00 178.00   0.50    0.78    --  107.39  19.00   0.00  140
 11  \w    104.00 135.00   0.50    0.19    --   62.00  80.00 117.49   62
 12  \w    102.00 135.00   0.50    0.78    --  107.39  37.00  60.00   66
 13  \w    105.00 176.00   0.50    0.78    --  107.39  57.00 120.00  142
 14  \w     96.00 176.00   0.50    0.78    --  107.39  37.00  90.00  160
 15  \w     95.00 153.00   0.50    0.78    --  107.39  57.00 -60.00  116
 16  \w    107.00 133.00   0.50    0.19    --   70.00  77.00-140.14   52
 17  \w     91.00 126.00   0.50    0.19    --   54.00  76.00-174.23   70
 18  \w     94.00 178.00   0.50    0.78    --  107.39  57.00 -90.00  168
 19  \w    100.00 176.00   0.50    0.78    --  107.39  37.00-120.00  152
 20  \w     87.00 129.00   0.50    0.78    --  107.39  77.00   0.00   84
 21  \w     50.00  77.00   0.50    0.19    --   70.00  77.00-140.14   54
 22  \w     39.00  81.00   0.50    0.19    --   58.00  73.00-149.34   84
 23  \w     38.00  64.00   0.50    0.19    --   62.00  79.00-107.23   52
 24  \w     45.00  70.00   0.50    0.19    --   66.00  73.00-141.86   50
 25  \w     30.00  55.00   0.50    0.19    --   54.00  79.00-100.79   50
 26  \w     28.00  54.00   0.50    0.19    --   48.17  77.00-120.00   52
 27  \w     32.00  77.00   0.50    0.19    --   54.00  75.00 -58.80   90
 28  \w     27.00  69.00   0.50    0.19    --   50.00  78.00  26.97   84
 29  \w     38.00  64.00   0.50    0.19    --   62.00  80.00  39.97   52
 30  \w     34.00  61.00   0.50    0.19    --   58.00  79.00  80.11   54
 31  \w     43.00  69.00   0.50    0.19    --   66.00  77.00  57.26   52
 32  \w     38.00  63.00   0.50    0.19    --   62.00  80.00 117.49   50
 33  \w     73.00 165.00   0.50    0.78    --   94.00  74.00 165.82  184
 34  \w     36.00  65.00   0.50    0.78    --  107.39 -57.00 120.00   58
 35  \w     36.00 106.00   0.50    0.78    --  107.39 -99.00  60.00  140
 36  \w     71.00 105.00   0.50    0.78    --  107.39-125.00 120.00   68
 37  \w     38.00  63.00   0.50    0.78    --  107.39 -57.00   0.00   50
 38  \w     36.00 103.00   0.50    0.78    --  107.39 -99.00 -30.00  134
 39  \w     76.00 106.00   0.50    0.78    --  107.39 -99.00 -90.00   60
 40  \w     58.00 109.00   0.50    0.78    --  107.39-125.00 -90.00  102
 41  \w     59.00 100.00   0.50    0.78    --  107.39 -99.00-180.00   82
 42  \w     45.00  71.00   0.50    0.78    --  107.39 -94.00-175.00   52
 43  \w     41.00  66.00   0.50    0.78    --  107.39 -57.00-120.00   50
 44  \w     35.00  65.00   0.50    0.78    --  107.39 -57.00 -60.00   60
 45  \w     39.00  64.00   0.50    0.78    --  107.39 -57.00 -30.00   50
 46  \w     36.00  61.00   0.50    0.78    --  107.39 -57.00  30.00   50
 47  \w     53.00 103.00   0.50    0.78    --  107.39 -99.00   0.00  100
 48  \w     37.00  64.00   0.50    0.78    --  107.39-125.00 120.00   54
 49  \w     36.00 107.00   0.50    0.78    --  107.39-106.00 140.96  142
 50  \w     41.00  66.00   0.50    0.78    --  107.39 -57.00  60.00   50
 51  \w     35.00  66.00   0.50    0.78    --  107.39 -57.00 150.00   62
 52  \w      0.00  25.00   0.50    0.19    --   22.00  88.00  76.16   50
 53  \w     13.00  38.00   0.50    0.19    --   42.00  91.00  84.18   50
 54  \w    -18.00  13.00   0.50    0.19    --   14.00 102.00  64.14   62
 55  \w    -62.00  -5.00   0.50    0.19    --  -48.17  94.00 -64.00  114
 56  \w      4.00  41.00   0.50    0.19    --   48.17 -37.00-120.00   74
 57  \w    -11.00  78.00   0.50    0.19    --   48.17 -94.00-175.00  178
 58  \w     39.00  72.00   0.50    0.78    --  107.39 -99.00 -90.00   66
 59  \w     32.00  63.00   0.50    0.19    --   54.00  76.00-174.23   62
 60  \w      8.00  40.00   0.50    0.19    --   38.00  92.00-174.72   64
 61  \w    -42.00 -16.00   0.50    0.19    --    6.00 130.00-109.41   52
 62  \w    -26.00  21.00   0.50    0.19    --  -48.17  19.00-150.00   94
 63  \w    -39.00 -13.00   0.50    0.78    --  -86.25  37.00-120.00   52
 64  \w    -62.00 -32.00   0.50    0.78    --  -86.25  57.00 -30.00   60
 65  \w    -71.00 -46.00   0.50    0.78    --  -86.25  94.00 -64.00   50
 66  \w    -94.00 -54.00   0.50    0.19    --  -48.17 -19.00-180.00   80
 67  \w    -76.00 -51.00   0.50    0.78    --  -74.00 -77.00-111.08   50
 68  \w    -91.00 -44.00   0.50    0.19    --  -48.17 -37.00 -60.00   94
 69  \w    -80.00 -55.00   0.50    0.78    --  -74.00 -68.00 -17.44   50
 70  \w    -82.00 -57.00   0.50    0.78    --  -78.00 -75.00 -81.03   50
 71  \w    -87.00 -62.00   0.50    0.78    --  -86.25 -79.00 -43.66   50
 72  \w    -92.00 -63.00   0.50    0.78    --  -86.25 -77.00 -30.00   58
 73  \w    -92.00 -66.00   0.50    0.78    --  -86.25 -72.00 -20.20   52
 74  \w    -97.00 -63.00   0.50    0.78    --  -86.25 -77.00 -60.00   68
 75  \w   -101.00 -66.00   0.50    0.78    --  -86.25 -77.00 -90.00   70
 76  \w    -96.00 -65.00   0.50    0.78    --  -86.25 -74.00-120.53   62
 77  \w    -89.00 -64.00   0.50    0.78    --  -86.25 -76.00-165.13   50
 78  \w   -108.00 -65.00   0.50    0.78    --  -86.25 -72.00-177.66   86
 79  \w   -112.00 -70.00   0.50    0.78    --  -86.25 -71.00-132.68   84
 80  \w   -137.00-107.00   0.50    0.78    --  -78.00 -75.00 -81.03   60
 81  \w   -134.00 -65.00   0.50    0.78    --  -86.25 -73.00-144.16  138
 82  \w   -133.00-108.00   0.50    0.78    --  -86.25 -76.00-165.13   50
 83  \w   -145.00-120.00   0.50    0.78    --  -86.25 -94.00-175.00   50
 84  \w   -156.00-121.00   0.50    0.78    --  -86.25 -71.00-132.68   70
 85  \w   -145.00-119.00   0.50    0.78    --  -86.25 -77.00 -90.00   52
 86  \w   -141.00-115.00   0.50    0.78    --  -86.25 -77.00 -60.00   52
 87  \w    -94.00 -63.00   0.50    0.78    --  -86.25 -77.00   0.00   62
 88  \w    -93.00 -64.00   0.50    0.78    --  -86.25 -76.00  61.26   58
 89  \w    -77.00 -52.00   0.50    0.78    --  -74.00 -75.00  76.77   50
 90  \w    -50.00 -25.00   0.50    0.19    --  -48.17 -77.00 120.00   50
 91  \w    -76.00 -51.00   0.50    0.78    --  -74.00 -76.00 112.00   50
 92  \w    -87.00 -62.00   0.50    0.19    --  -48.17 -77.00 120.00   50
 93  \w    -83.00 -58.00   0.50    0.78    --  -78.00 -74.00 153.18   50
 94  \w    -85.00 -60.00   0.50    0.78    --  -82.00 -74.00 169.82   50
 95  \w    -91.00 -65.00   0.50    0.78    --  -86.25 -77.00 150.00   52
 96  \w    -92.00 -66.00   0.50    0.78    --  -86.25 -70.00 100.65   52
 97  \w    -85.00 -60.00   0.50    0.78    --  -82.00 -77.00  81.45   50
 98  \w    -99.00 -70.00   0.50    0.78    --  -86.25 -73.00  76.53   58
 99  \w    -93.00 -64.00   0.50    0.78    --  -86.25 -76.00 120.83   58
100  \w    -93.00 -65.00   0.50    0.78    --  -86.25 -74.00 168.24   56
101  \w    -89.00 -64.00   0.50    0.78    --  -86.25 -75.00  96.02   50
102  \w   -102.00 -65.00   0.50    0.78    --  -86.25 -76.00  48.35   74
103  \w   -109.00 -63.00   0.50    0.78    --  -86.25 -77.00  30.00   92
104  \w   -115.00 -67.00   0.50    0.78    --  -86.25 -73.00 132.37   96
105  \w   -130.00-104.00   0.50    0.78    --  -86.25 -75.00  96.02   52
106  \w   -159.00-133.00   0.50    0.78    --  -86.25 -77.00   0.00   52
107  \w   -156.00-131.00   0.50    0.78    --  -86.25 -76.00  48.35   50
108  \w   -155.00-115.00   0.50    0.78    --  -86.25 -73.00  76.53   80
109  \w   -155.00-129.00   0.50    0.78    --  -86.25 -77.00 150.00   52
110  \w   -152.00-113.00   0.50    0.78    --  -86.25 -70.00 100.65   78
111  \w   -154.00-128.00   0.50    0.78    --  -86.25 -76.00  61.26   52
112  \w   -154.00-129.00   0.50    0.78    --  -86.25 -77.00  30.00   50
113  \w   -156.00-131.00   0.50    0.78    --  -86.25 -79.00 -43.66   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0386305000
_diffrn_orient_matrix_UB_12      0.1937927000
_diffrn_orient_matrix_UB_13      0.0447434000
_diffrn_orient_matrix_UB_21      -0.0409468000
_diffrn_orient_matrix_UB_22      -0.0568257000
_diffrn_orient_matrix_UB_23      0.0770793000
_diffrn_orient_matrix_UB_31      0.0806342000
_diffrn_orient_matrix_UB_32      -0.1216543000
_diffrn_orient_matrix_UB_33      0.0352876000
_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  0.0728
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45459
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.073
_diffrn_reflns_theta_min         3.632
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.0056(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0658
_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^)+(0.1875P)^2^+0.4091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2688
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3067
_reflns_number_total             3468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj01423a2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7062618--7062620.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062620
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.969
_oxdiff_exptl_absorpt_empirical_full_min 0.578
_oxdiff_exptl_absorpt_empirical_full_max 1.807
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_oxdiff_digest_frames
;
0186c931aec372f5da699b8684d38a3415000374315
;
_diffrn_oxdiff_digest_hkl
;
0174032e5e99c36a0b4b8ce20f6f75eae46bbf
;
_shelx_res_checksum              74972