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_7245304
_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         'C29 H24 Se'
_chemical_formula_sum            'C29 H24 Se'
_chemical_formula_weight         451.473
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-05-04 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                71.458(2)
_cell_angle_beta                 73.161(2)
_cell_angle_gamma                63.999(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9628(2)
_cell_length_b                   10.1107(2)
_cell_length_c                   12.9334(2)
_cell_measurement_reflns_used    10359
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.4120
_cell_measurement_theta_min      5.0300
_cell_volume                     1092.75(4)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9687
_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     41.00  87.00   0.50    1.50    --    0.00  82.00-120.00   92
  2  \w     51.00  76.00   0.50    1.50    --    0.00  37.00-120.00   50
  3  \w    -85.00  19.00   0.50    1.50    --    0.00 -19.00-120.00  208
  4  \w    -29.00  29.00   0.50    1.50    --    0.00  82.00-120.00  116
  5  \w    -19.00  39.00   0.50    1.50    --    0.00  37.00-120.00  116
  6  \w     87.00 197.00   0.50    1.50    --  107.20  45.00  90.00  220
  7  \w     18.00 139.00   0.50    1.50    --  107.20 -82.00 120.00  242
  8  \w     19.00 132.00   0.50    1.50    --  107.20 -61.00 -90.00  226
  9  \w     93.00 171.00   0.50    1.50    --  107.20  30.00-150.00  156
 10  \w     52.00 107.00   0.50    1.50    --  107.20 -82.00  30.00  110
 11  \w     40.00 130.00   0.50    1.50    --  107.20 -82.00 -90.00  180
 12  \w     34.00  60.00   0.50    1.50    --  107.20 -82.00  60.00   52
 13  \w    138.00 186.00   0.50    1.50    --  107.20  30.00 120.00   96
 14  \w     82.00 153.00   0.50    1.50    --  107.20  82.00 150.00  142
 15  \w     92.00 117.00   0.50    1.50    --  107.20 -82.00-180.00   50
 16  \w     19.00  64.00   0.50    1.50    --  107.20 -82.00-180.00   90
 17  \w     87.00 112.00   0.50    1.50    --  107.20 -82.00 -60.00   50
 18  \w     19.00 132.00   0.50    1.50    --  107.20 -61.00   0.00  226
 19  \w     21.00 123.00   0.50    1.50    --  107.20 -61.00 120.00  204
 20  \w     93.00 148.00   0.50    1.50    --  107.20  30.00 -90.00  110
 21  \w     89.00 115.00   0.50    1.50    --  107.20 -82.00-150.00   52
 22  \w     91.00 190.00   0.50    1.50    --  107.20  30.00-120.00  198
;
_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      -0.0805352000
_diffrn_orient_matrix_UB_12      0.1543764000
_diffrn_orient_matrix_UB_13      -0.0729045000
_diffrn_orient_matrix_UB_21      0.0849331000
_diffrn_orient_matrix_UB_22      -0.0638293000
_diffrn_orient_matrix_UB_23      -0.1045235000
_diffrn_orient_matrix_UB_31      -0.1298065000
_diffrn_orient_matrix_UB_32      -0.0482090000
_diffrn_orient_matrix_UB_33      0.0071486000
_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  0.0284
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.9965
_diffrn_reflns_Laue_measured_fraction_max 0.9687
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12419
_diffrn_reflns_point_group_measured_fraction_full 0.9965
_diffrn_reflns_point_group_measured_fraction_max 0.9687
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.70
_diffrn_reflns_theta_min         4.99
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.402
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57688
_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 greenish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       cube
_exptl_crystal_F_000             463.571
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.5256
_refine_diff_density_min         -0.6478
_refine_diff_density_rms         0.0788
_refine_ls_d_res_high            0.7836
_refine_ls_d_res_low             8.8605
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0273
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0273
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.9925P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4483
_reflns_number_total             4610
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2gc02256g2.cif
_cod_data_source_block           exp_1098_NM-756_
_cod_depositor_comments
'Adding full bibliography for 7245304--7245306.cif.'
_cod_database_code               7245304
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00P(H00b,H00e), C00T(H00s,H00t)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K),
 C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C00U(H00U), C007(H007),
 C008(H008), C009(H009)
2.c Idealised Me refined as rotating group:
 C00S(H00l,H00m,H00p)
;
_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 2.335
_oxdiff_exptl_absorpt_empirical_full_min 0.604