Regioselective peri-C–H selenylation of aromatic compounds with weakly coordinating ketone groups
Duan, Bingbing; Wu, Yao; Gao, Yi; Ying, Linkun; Tang, Jielin; Hu, Shiyu; Zhao, Qiuhua; Song, Zengqiang; Chemical Communications  (2022) –; doi:10.1039/D2CC04030A

data_7130776
_publ_section_title
;
 Regioselective peri-C--H selenylation of aromatic compounds with weakly
 coordinating ketone groups
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04030A
_journal_year                    2022
_chemical_formula_moiety         'C20 H19 N O2 Se'
_chemical_formula_sum            'C20 H19 N O2 Se'
_chemical_formula_weight         384.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-23
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-09-05 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                74.087(4)
_cell_angle_beta                 74.630(3)
_cell_angle_gamma                81.377(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0338(3)
_cell_length_b                   8.4987(4)
_cell_length_c                   13.3369(5)
_cell_measurement_reflns_used    6393
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      28.9770
_cell_measurement_theta_min      3.5790
_cell_volume                     841.45(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_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_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_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    -11.00  14.00   1.00    1.44    --   18.74  77.00 -60.00   25
  2  \w    -50.00  44.00   1.00    1.44    --   18.74 -38.00 120.00   94
  3  \w     26.00  86.00   1.00    1.44    --   18.74  38.00 -60.00   60
  4  \w     -9.00  31.00   1.00    1.44    --   18.74  77.00 150.00   40
  5  \w    -48.00  38.00   1.00    1.44    --   18.74 -57.00  30.00   86
  6  \w     -7.00  19.00   1.00    1.44    --   18.74  38.00 -60.00   26
  7  \w    -42.00  10.00   1.00    1.44    --  -18.85 -77.00 -60.00   52
  8  \w     16.00  87.00   1.00    1.44    --   18.58  57.00-180.00   71
  9  \w    -40.00  49.00   1.00    1.44    --   18.58 -77.00 -90.00   89
 10  \w     -5.00  59.00   1.00    1.44    --   18.58 -99.00   0.00   64
 11  \w     25.00  60.00   1.00    1.44    --   18.58 -99.00-180.00   35
 12  \w     -1.00  87.00   1.00    1.44    --   18.58  57.00  60.00   88
 13  \w     16.00  46.00   1.00    1.44    --  -18.78  57.00 -60.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0685907000
_diffrn_orient_matrix_UB_12      0.0607868000
_diffrn_orient_matrix_UB_13      0.0103760000
_diffrn_orient_matrix_UB_21      -0.0570391000
_diffrn_orient_matrix_UB_22      -0.0623198000
_diffrn_orient_matrix_UB_23      0.0278397000
_diffrn_orient_matrix_UB_31      0.0220098000
_diffrn_orient_matrix_UB_32      -0.0023585000
_diffrn_orient_matrix_UB_33      0.0485316000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13102
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.101
_diffrn_reflns_theta_min         3.307
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0259P)^2^+0.2014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0708
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3500
_reflns_number_total             3985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04030a2.cif
_cod_data_source_block           20220829-d-276-1-200k
_cod_database_code               7130776
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H19 N O2 Se'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C20(H20), C9(H9), C17(H17), C8(H8), C7(H7), C19(H19),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              81010
_shelx_hkl_checksum              58587
_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 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.888