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_7245306
_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         'C27 H20 Se'
_chemical_formula_sum            'C27 H20 Se'
_chemical_formula_weight         423.419
_chemical_name_systematic        NM-731
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-01
_audit_creation_method
;
Olex2 1.5-alpha
(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                 100.258(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2182(3)
_cell_length_b                   10.3531(3)
_cell_length_c                   17.3831(5)
_cell_measurement_reflns_used    5183
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.2670
_cell_measurement_theta_min      4.0480
_cell_volume                     1986.66(10)
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (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 0.9958
_diffrn_measured_fraction_theta_max 0.9515
_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     39.00  88.00   0.50    2.00    --    0.00  37.00  90.00   98
  2  \w     -3.00  23.00   0.50    2.00    --    0.00  77.00  60.00   52
  3  \w    -30.00  -3.00   0.50    2.00    --    0.00  82.00 120.00   54
  4  \w      0.00  59.00   0.50    2.00    --    0.00  57.00-150.00  118
  5  \w    -16.00  86.00   0.50    2.00    --    0.00  37.00 -60.00  204
  6  \w     64.00  89.00   0.50    2.00    --    0.00  77.00  60.00   50
  7  \w     87.00 194.00   0.50    8.00    --  107.20  45.00-120.00  214
  8  \w     38.00 137.00   0.50    8.00    --  107.20 -82.00 -90.00  198
  9  \w     19.00  44.00   0.50    8.00    --  107.20 -77.00  90.00   50
 10  \w    103.00 134.00   0.50    8.00    --  107.20  30.00 -30.00   62
 11  \w    137.00 186.00   0.50    8.00    --  107.20  30.00 -30.00   98
 12  \w     27.00 124.00   0.50    8.00    --  107.20 -61.00  90.00  194
 13  \w     83.00 109.00   0.50    8.00    --  107.20 -45.00 150.00   52
 14  \w     62.00 138.00   0.50    8.00    --  107.20 -77.00  90.00  152
 15  \w     97.00 164.00   0.50    8.00    --  107.20   0.00  60.00  134
 16  \w     21.00  83.00   0.50    8.00    --  107.20   0.00  60.00  124
;
_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      0.0527925000
_diffrn_orient_matrix_UB_12      -0.1282024000
_diffrn_orient_matrix_UB_13      -0.0239544000
_diffrn_orient_matrix_UB_21      0.1290188000
_diffrn_orient_matrix_UB_22      0.0505750000
_diffrn_orient_matrix_UB_23      0.0298290000
_diffrn_orient_matrix_UB_31      -0.0043138000
_diffrn_orient_matrix_UB_32      -0.0560621000
_diffrn_orient_matrix_UB_33      0.0816009000
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.9958
_diffrn_reflns_Laue_measured_fraction_max 0.9515
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10388
_diffrn_reflns_point_group_measured_fraction_full 0.9958
_diffrn_reflns_point_group_measured_fraction_max 0.9515
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         80.04
_diffrn_reflns_theta_min         4.00
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68213
_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            'metallic colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             862.989
_exptl_crystal_preparation       DCM,Hexane
_exptl_crystal_recrystallization_method Cubic
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.6378
_refine_diff_density_min         -0.9648
_refine_diff_density_rms         0.0928
_refine_ls_d_res_high            0.7827
_refine_ls_d_res_low             11.0389
_refine_ls_goodness_of_fit_ref   1.0185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0185
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0835P)^2^+1.8040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1256
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                3676
_reflns_number_total             4136
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2gc02256g2.cif
_cod_data_source_block           exp_1124_NM-731
_cod_depositor_comments
'Adding full bibliography for 7245304--7245306.cif.'
_cod_database_code               7245306
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C009(H009)
2.b Idealised Me refined as rotating group:
 C00S(H00b,H00l,H00s)
;
_olex2_submission_original_sample_id NM-731
_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 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.557