Recyclable iodine-catalyzed radical selenylative annulation of 2-alkynyl biaryls with diselenides in water: a green approach to selanyl polycyclic aromatic hydrocarbons and polycyclic heteroaromatics
Mukherjee, Nilanjana; Satyanarayana, Appanapalli N. V.; Singh, Priti; Dixit, Mudit; Chatterjee, Tanmay; Green Chemistry 24 (2022) 7029–7038; doi:10.1039/D2GC02256G

data_7245305
_publ_section_title
;
 Recyclable iodine-catalyzed radical selenylative annulation of 2-alkynyl
 biaryls with diselenides in water: a green approach to selanyl polycyclic
 aromatic hydrocarbons and polycyclic heteroaromatics
;
_journal_issue                   18
_journal_name_full               'Green Chemistry'
_journal_page_first              7029
_journal_page_last               7038
_journal_paper_doi               10.1039/D2GC02256G
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C26 H17 Cl Se'
_chemical_formula_sum            'C26 H17 Cl Se'
_chemical_formula_weight         443.80
_chemical_name_systematic        NM-730
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-03 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.7750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3921(2)
_cell_length_b                   10.18330(10)
_cell_length_c                   13.1358(2)
_cell_measurement_reflns_used    7962
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.1990
_cell_measurement_theta_min      5.5900
_cell_volume                     1960.65(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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      100
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.971
_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     50.00  89.00   0.50    1.00    --    0.00  37.00 -60.00   78
  2  \w    -10.00  47.00   0.50    1.00    --    0.00  37.00 -60.00  114
  3  \w    -49.00  28.00   0.50    1.00    --    0.00 -77.00-180.00  154
  4  \w     43.00  77.00   0.50    1.00    --    0.00  37.00   0.00   68
  5  \w     19.00 127.00   0.50    3.20    --  107.20 -30.00 150.00  216
  6  \w     19.00 129.00   0.50    3.20    --  107.20 -82.00  30.00  220
  7  \w     94.00 190.00   0.50    3.20    --  107.20  77.00 120.00  192
  8  \w     93.00 140.00   0.50    3.20    --  107.20 -82.00  60.00   94
  9  \w     90.00 139.00   0.50    3.20    --  107.20 -82.00 -60.00   98
 10  \w     89.00 193.00   0.50    3.20    --  107.20  30.00  90.00  208
 11  \w    107.00 147.00   0.50    3.20    --  107.20  30.00-180.00   80
 12  \w     81.00 127.00   0.50    3.20    --  107.20 -45.00   0.00   92
 13  \w     38.00 125.00   0.50    3.20    --  107.20 -82.00 -30.00  174
 14  \w     43.00  69.00   0.50    3.20    --  107.20 -45.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0877013000
_diffrn_orient_matrix_UB_12      0.0807563000
_diffrn_orient_matrix_UB_13      -0.0154942000
_diffrn_orient_matrix_UB_21      0.0546946000
_diffrn_orient_matrix_UB_22      0.1277984000
_diffrn_orient_matrix_UB_23      0.0053569000
_diffrn_orient_matrix_UB_31      -0.0188697000
_diffrn_orient_matrix_UB_32      -0.0048216000
_diffrn_orient_matrix_UB_33      -0.1221454000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12473
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.509
_diffrn_reflns_theta_min         5.289
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_preparation       DCM,Hexane
_exptl_crystal_recrystallization_method Monoclinic
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0482P)^2^+1.0458P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3844
_reflns_number_total             4133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02256g2.cif
_cod_data_source_block           exp_1123_nm-730
_cod_depositor_comments
'Adding full bibliography for 7245304--7245306.cif.'
_cod_original_cell_volume        1960.65(4)
_cod_database_code               7245305
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.829
_shelx_estimated_absorpt_t_min   0.697
_olex2_refinement_description
;
;
_shelx_res_checksum              90683
_olex2_submission_original_sample_id NM-730
_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 1.701
_oxdiff_exptl_absorpt_empirical_full_min 0.689