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_4038697
_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_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 N O2 Se'
_chemical_formula_sum            'C21 H23 N O2 Se'
_chemical_formula_weight         400.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-12-21
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.0693(8)
_cell_length_b                   10.9616(8)
_cell_length_c                   29.0524(19)
_cell_measurement_reflns_used    2139
_cell_measurement_temperature    146(2)
_cell_measurement_theta_max      27.3010
_cell_measurement_theta_min      4.1380
_cell_volume                     3843.6(5)
_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      146(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.6518
_diffrn_measurement_details
;
  1 omega  -69.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -19.0000  -30.0000 60

  2 omega   35.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  178.0000 -180.0000 35

  3 omega  -51.00    8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000 -120.0000 59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0152180000
_diffrn_orient_matrix_UB_12      0.0084891000
_diffrn_orient_matrix_UB_13      0.0233731000
_diffrn_orient_matrix_UB_21      -0.0479629000
_diffrn_orient_matrix_UB_22      0.0363043000
_diffrn_orient_matrix_UB_23      0.0035054000
_diffrn_orient_matrix_UB_31      -0.0303730000
_diffrn_orient_matrix_UB_32      -0.0529911000
_diffrn_orient_matrix_UB_33      0.0061376000
_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  0.0441
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            10925
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85828
_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    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         6109
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0296P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                4864
_reflns_number_total             6109
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00921_si_001.cif
_cod_data_source_block           exp_5750
_cod_database_code               4038697
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32