Silver-Catalyzed Remote C5-H Selenylation of Indoles.
Song, Wei-Hong; Shi, Jia; Chen, Xiaohong; Song, Guoyong; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00921

data_4038696
_publ_section_title
;
 Silver-Catalyzed Remote C5-H Selenylation of Indoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00921
_journal_year                    2020
_chemical_formula_moiety         'C20 H20 Cl N O Se'
_chemical_formula_sum            'C20 H20 Cl N O Se'
_chemical_formula_weight         404.78
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-18
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.970(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6868(2)
_cell_length_b                   14.0452(10)
_cell_length_c                   22.1678(7)
_cell_measurement_reflns_used    2705
_cell_measurement_temperature    110.10(10)
_cell_measurement_theta_max      29.1180
_cell_measurement_theta_min      3.6940
_cell_volume                     1757.51(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.10(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9955
_diffrn_measured_fraction_theta_max 0.8497
_diffrn_measurement_details
;
  1 omega  -24.00   23.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000  -90.0000 47

  2 omega  -46.00   75.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335    0.0000   60.0000 121

  3 omega  -19.00    9.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000   90.0000 28

  4 omega    0.00   39.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210   57.0000 -180.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0396920000
_diffrn_orient_matrix_UB_12      0.0478086000
_diffrn_orient_matrix_UB_13      -0.0036993000
_diffrn_orient_matrix_UB_21      0.0677924000
_diffrn_orient_matrix_UB_22      0.0123708000
_diffrn_orient_matrix_UB_23      0.0279190000
_diffrn_orient_matrix_UB_31      0.0983106000
_diffrn_orient_matrix_UB_32      0.0107416000
_diffrn_orient_matrix_UB_33      -0.0156897000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7939
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0306P)^2^+0.3647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0760
_reflns_number_gt                2939
_reflns_number_total             3434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00921_si_002.cif
_cod_data_source_block           exp_5798
_cod_database_code               4038696
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32