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_7062619
_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            'C18 H17 Cl N2 O2'
_chemical_formula_weight         328.79
_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                 112.1240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.41130(10)
_cell_length_b                   16.82570(10)
_cell_length_c                   10.91390(10)
_cell_measurement_reflns_used    42907
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      77.1160
_cell_measurement_theta_min      2.6200
_cell_volume                     1600.99(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 0.999
_diffrn_measured_fraction_theta_max 0.989
_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     31.00  56.50   0.50    0.20    --   54.00  79.00 -56.08   51
  2  \w     36.00  71.50   0.50    0.20    --   48.29  37.00-120.00   71
  3  \w     76.00 110.00   0.50    0.20    --   48.29  37.00-120.00   68
  4  \w     94.00 119.50   0.50    0.20    --   54.00  79.00 -56.08   51
  5  \w    100.80 126.30   0.50    0.20    --   54.00  80.00 -27.29   51
  6  \w     85.00 111.00   0.50    0.20    --   54.00  78.00   7.50   52
  7  \w    116.00 142.00   0.50    0.80    --  107.75 133.00  63.00   52
  8  \w    124.00 150.00   0.50    0.80    --  107.75  77.00  90.00   52
  9  \w    143.00 171.00   0.50    0.80    --  107.75  77.00 120.00   56
 10  \w    126.00 168.00   0.50    0.80    --  107.75  77.00 150.00   84
 11  \w     85.00 137.00   0.50    0.80    --  107.75  77.00  30.00  104
 12  \w    144.00 175.50   0.50    0.80    --  107.75  77.00   0.00   63
 13  \w    132.00 174.00   0.50    0.80    --  107.75  77.00 -60.00   84
 14  \w    142.00 176.00   0.50    0.80    --  107.75  77.00-120.00   68
 15  \w    132.00 170.00   0.50    0.80    --  107.75  45.00-150.00   76
 16  \w    120.00 146.00   0.50    0.80    --  107.75  77.00-180.00   52
 17  \w    119.00 176.50   0.50    0.80    --  107.75  77.00-150.00  115
 18  \w    149.00 175.00   0.50    0.80    --  107.75 125.00-150.00   52
 19  \w    129.00 175.00   0.50    0.80    --  107.75 125.00 -90.00   92
 20  \w    129.00 177.00   0.50    0.80    --  107.75  77.00 -30.00   96
 21  \w    125.00 172.50   0.50    0.80    --  107.75  45.00   0.00   95
 22  \w    109.00 134.50   0.50    0.80    --  107.75 136.00-119.00   51
 23  \w    105.00 131.00   0.50    0.80    --  107.75 125.00-150.00   52
 24  \w     94.00 176.00   0.50    0.80    --  107.75  77.00 -90.00  164
 25  \w     93.00 149.00   0.50    0.80    --  107.75  61.00 -30.00  112
 26  \w     92.00 145.50   0.50    0.80    --  107.75  61.00 -90.00  107
 27  \w     91.00 165.00   0.50    0.80    --  107.75  61.00-180.00  148
 28  \w     86.00 125.50   0.50    0.80    --  107.75  77.00 -60.00   79
 29  \w     85.00 124.50   0.50    0.80    --  107.75  77.00 -30.00   79
 30  \w     94.00 163.50   0.50    0.80    --  107.75  61.00  30.00  139
 31  \w     93.00 118.50   0.50    0.80    --  107.75  77.00  90.00   51
 32  \w     93.00 173.00   0.50    0.80    --  107.75  61.00 150.00  160
 33  \w     93.00 167.00   0.50    0.80    --  107.75  61.00 120.00  148
 34  \w     85.00 136.50   0.50    0.80    --  107.75  77.00 120.00  103
 35  \w     96.00 172.00   0.50    0.80    --  107.75  61.00  90.00  152
 36  \w     91.00 155.00   0.50    0.80    --  107.75  61.00 -60.00  128
 37  \w     86.00 116.00   0.50    0.80    --  107.75  77.00-180.00   60
 38  \w     86.00 114.00   0.50    0.80    --  107.75  77.00-150.00   56
 39  \w     85.00 127.00   0.50    0.80    --  107.75  77.00-120.00   84
 40  \w     93.00 133.00   0.50    0.80    --  107.75  61.00-150.00   80
 41  \w     79.00 155.00   0.50    0.80    --  102.00  79.00-138.57  152
 42  \w     91.00 126.50   0.50    0.80    --  107.75  61.00   0.00   71
 43  \w     91.00 175.00   0.50    0.80    --  107.75  61.00  60.00  168
 44  \w     86.00 115.50   0.50    0.80    --  107.75  77.00 150.00   59
 45  \w     72.00 129.50   0.50    0.20    --   58.00  80.00 135.85  115
 46  \w     85.00 143.00   0.50    0.80    --  107.75  77.00  60.00  116
 47  \w     85.00 132.50   0.50    0.80    --  107.75  77.00   0.00   95
 48  \w     64.00  90.00   0.50    0.20    --   54.00  80.00-121.53   52
 49  \w     37.00  72.50   0.50    0.20    --   58.00  74.00 -77.91   71
 50  \w     41.00  68.50   0.50    0.20    --   62.00  72.00-105.59   55
 51  \w     30.00  55.50   0.50    0.20    --   54.00  80.00-121.53   51
 52  \w     39.00  64.50   0.50    0.20    --   62.00  79.00-174.36   51
 53  \w     41.00  66.50   0.50    0.20    --   62.00  74.00-177.90   51
 54  \w     10.00  35.50   0.50    0.20    --   38.00  88.00 -91.78   51
 55  \w     30.00  55.50   0.50    0.20    --   54.00  80.00 -27.29   51
 56  \w     39.00  69.00   0.50    0.20    --   58.00  72.00 -13.71   60
 57  \w     41.00  67.00   0.50    0.20    --   62.00  73.00   9.53   52
 58  \w     30.00  68.00   0.50    0.20    --   54.00  80.00  30.00   76
 59  \w     42.00  67.50   0.50    0.20    --   62.00  72.00  90.89   51
 60  \w     39.00  64.50   0.50    0.20    --   62.00  78.00 106.72   51
 61  \w     34.00  59.50   0.50    0.20    --   58.00  80.00 135.85   51
 62  \w     39.00 122.50   0.50    0.20    --   48.29  19.00 120.00  167
 63  \w     40.00  66.00   0.50    0.80    --  107.75 -94.00   0.00   52
 64  \w     75.00 101.00   0.50    0.80    --  107.75 -94.00   0.00   52
 65  \w     80.00 117.50   0.50    0.80    --  107.75-133.00  -5.00   75
 66  \w     79.00 108.50   0.50    0.80    --  107.75-125.00 -60.00   59
 67  \w     82.00 111.50   0.50    0.80    --  107.75-125.00 -30.00   59
 68  \w     70.00 111.50   0.50    0.80    --  107.75-125.00 -90.00   83
 69  \w     48.00 109.50   0.50    0.80    --  107.75-125.00  30.00  123
 70  \w     84.00 110.00   0.50    0.80    --  107.75-125.00  90.00   52
 71  \w     71.00 119.00   0.50    0.80    --  107.75-136.00 176.00   96
 72  \w     59.00  99.00   0.50    0.80    --  107.75 -94.00 150.00   80
 73  \w     54.00 111.50   0.50    0.80    --  107.75-125.00 150.00  115
 74  \w     41.00  98.50   0.50    0.20    --   48.29-136.00 176.00  115
 75  \w     35.00  96.50   0.50    0.80    --  107.75 -94.00  90.00  123
 76  \w     42.00 107.50   0.50    0.80    --  107.75-125.00   0.00  131
 77  \w     40.00  99.50   0.50    0.20    --   48.29-133.00  -5.00  119
 78  \w     39.00  69.00   0.50    0.80    --  107.75 -77.00 -90.00   60
 79  \w     42.00  67.50   0.50    0.80    --  107.75 -61.00-150.00   51
 80  \w     37.00  91.00   0.50    0.80    --  107.75 -77.00-150.00  108
 81  \w     35.00  60.50   0.50    0.80    --  107.75 -61.00-120.00   51
 82  \w     39.00  83.00   0.50    0.80    --  107.75 -77.00-180.00   88
 83  \w     35.00  60.50   0.50    0.80    --  107.75-125.00 -90.00   51
 84  \w     38.00  63.50   0.50    0.80    --  107.75-125.00 -60.00   51
 85  \w     35.00  88.50   0.50    0.80    --  107.75 -77.00  30.00  107
 86  \w     38.00  64.00   0.50    0.80    --  107.75 -61.00  30.00   52
 87  \w     37.00 105.00   0.50    0.80    --  107.75 -94.00  30.00  136
 88  \w     35.00  68.50   0.50    0.80    --  107.75 -61.00 -90.00   67
 89  \w     45.00  70.50   0.50    0.80    --  107.75 -61.00 -30.00   51
 90  \w     43.00 103.00   0.50    0.80    --  107.75 -94.00-180.00  120
 91  \w     12.00  38.00   0.50    0.20    --   38.00  91.00  35.42   52
 92  \w     32.00  57.50   0.50    0.20    --   54.00  78.00   7.50   51
 93  \w      7.00  32.50   0.50    0.20    --   38.00  94.00   6.10   51
 94  \w    -11.00  23.00   0.50    0.20    --   18.00  95.00  -6.41   68
 95  \w     12.00  37.50   0.50    0.20    --   38.00  84.00 148.18   51
 96  \w    -15.00  17.00   0.50    0.20    --   18.00  98.00 166.02   64
 97  \w    -62.00 -37.50   0.50    0.20    --  -48.29 133.00  63.00   49
 98  \w    -78.00 -53.50   0.50    0.80    --  -86.25 133.00  63.00   49
 99  \w    -80.00 -55.50   0.50    0.20    --  -48.29 136.00-119.00   49
100  \w    -73.00 -47.50   0.50    0.20    --  -66.00 -67.00-126.04   51
101  \w    -58.00 -32.00   0.50    0.20    --  -54.00 -76.00-141.60   52
102  \w    -70.00 -44.00   0.50    0.20    --  -66.00 -79.00-172.51   52
103  \w    -78.00 -52.50   0.50    0.80    --  -70.00 -64.00 -95.39   51
104  \w    -76.00 -50.50   0.50    0.80    --  -74.00 -79.00-136.70   51
105  \w    -85.00 -59.50   0.50    0.80    --  -82.00 -77.00-102.75   51
106  \w    -86.00 -60.00   0.50    0.80    --  -82.00 -78.00 -67.35   52
107  \w    -81.00 -55.50   0.50    0.80    --  -78.00 -76.00 -36.64   51
108  \w    -63.00 -37.50   0.50    0.20    --  -58.00 -73.00   9.68   51
109  \w    -71.00 -27.00   0.50    0.20    --  -48.29 -77.00  60.00   88
110  \w    -78.00 -52.50   0.50    0.80    --  -70.00 -68.00  67.07   51
111  \w    -76.20 -50.70   0.50    0.80    --  -70.00 -68.00 114.58   51
112  \w    -77.00 -51.50   0.50    0.80    --  -70.00 -67.00  44.50   51
113  \w    -81.00 -55.50   0.50    0.80    --  -74.00 -65.00  -2.13   51
114  \w    -85.00 -59.50   0.50    0.80    --  -82.00 -77.00   9.29   51
115  \w    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00  30.00   51
116  \w    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00  90.00   51
117  \w    -86.00 -60.50   0.50    0.80    --  -78.00 -71.00 144.02   51
118  \w    -81.00 -55.50   0.50    0.80    --  -74.00 -66.00 163.42   51
119  \w    -91.00 -65.50   0.50    0.80    --  -86.25 -72.00 127.98   51
120  \w    -92.00 -64.50   0.50    0.80    --  -86.25 -74.00 160.54   55
121  \w    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00 120.00   51
122  \w    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00  60.00   51
123  \w    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00   0.00   51
124  \w    -89.00 -63.00   0.50    0.80    --  -86.25 -80.00 -32.19   52
125  \w    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00 -90.00   51
126  \w    -95.00 -69.50   0.50    0.80    --  -86.25 -62.00 -99.98   51
127  \w    -90.00 -64.00   0.50    0.80    --  -86.25 -77.00-150.00   52
128  \w    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00-180.00   51
129  \w    -97.00 -67.00   0.50    0.80    --  -86.25 -75.00-115.04   60
130  \w    -90.00 -64.50   0.50    0.80    --  -86.25 -75.00 -48.11   51
131  \w    -87.00 -62.50   0.50    0.80    --  -86.25 -80.00-133.45   49
132  \w   -108.00 -68.50   0.50    0.20    --  -48.29-133.00  -5.00   79
133  \w   -118.00 -92.50   0.50    0.20    --  -48.29-136.00 176.00   51
134  \w   -136.00-111.50   0.50    0.80    --  -86.25-136.00 176.00   49
135  \w   -146.00 -60.50   0.50    0.80    --  -78.00 -64.00  14.83  171
136  \w   -137.00-112.50   0.50    0.80    --  -86.25-133.00  -5.00   49
137  \w   -133.00 -67.50   0.50    0.80    --  -86.25 -67.00 -29.04  131
138  \w   -135.00-109.00   0.50    0.20    --  -66.00 -79.00-172.51   52
139  \w   -159.00-133.00   0.50    0.80    --  -86.25 -77.00-150.00   52
;
_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      -0.0497419000
_diffrn_orient_matrix_UB_12      -0.0803104000
_diffrn_orient_matrix_UB_13      0.0387930000
_diffrn_orient_matrix_UB_21      0.0952264000
_diffrn_orient_matrix_UB_22      -0.0439613000
_diffrn_orient_matrix_UB_23      -0.0667708000
_diffrn_orient_matrix_UB_31      0.1402940000
_diffrn_orient_matrix_UB_32      0.0013488000
_diffrn_orient_matrix_UB_33      0.1313434000
_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  0.1170
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            56280
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.336
_diffrn_reflns_theta_min         5.104
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68317
_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    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0655
_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^+1.2500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2879
_reflns_number_total             3363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj01423a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7062618--7062620.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062619
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.810
_shelx_estimated_absorpt_t_max   0.898
_oxdiff_exptl_absorpt_empirical_full_min 0.596
_oxdiff_exptl_absorpt_empirical_full_max 2.526
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_oxdiff_digest_frames
;
0182ab7078d715560ade0a0830909ca45c0003686e3
;
_diffrn_oxdiff_digest_hkl
;
01b80112dee8ee39c9738f5fea6c80a777c7c6
;
_shelx_res_checksum              54536