Electrochemical regioselective selenylation/oxidation of N-alkylisoquinolinium salts via double C(sp<sup>2</sup>)-H bond functionalization.
Liu, Xiang; Wang, Yajun; Song, Dan; Wang, Yuhan; Cao, Hua; Chemical communications (Cambridge, England) 56 (2020) 15325–15328; doi:10.1039/d0cc06778d

data_7127601
_publ_section_title
;
 Electrochemical regioselective selenylation/oxidation of
 N-alkylisoquinolinium salts via double C(sp<sup>2</sup>)-H bond
 functionalization.
;
_journal_issue                   97
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15325
_journal_page_last               15328
_journal_paper_doi               10.1039/d0cc06778d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C22 H17 N O Se'
_chemical_formula_sum            'C22 H17 N O Se'
_chemical_formula_weight         390.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-27
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-08-01 deposited with the CCDC.	2020-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5032(6)
_cell_length_b                   14.7847(17)
_cell_length_c                   21.373(2)
_cell_measurement_reflns_used    1578
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6010
_cell_measurement_theta_min      2.7640
_cell_volume                     1739.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     -8.00  82.00   1.00    6.50    --   11.74  57.00  60.00   90
  2  \w    -63.00  37.00   1.00    6.50    --   11.74 -77.00 -60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0029592000
_diffrn_orient_matrix_UB_12      0.0028738000
_diffrn_orient_matrix_UB_13      0.0331030000
_diffrn_orient_matrix_UB_21      -0.0016436000
_diffrn_orient_matrix_UB_22      -0.0479302000
_diffrn_orient_matrix_UB_23      0.0020418000
_diffrn_orient_matrix_UB_31      0.1287702000
_diffrn_orient_matrix_UB_32      -0.0005616000
_diffrn_orient_matrix_UB_33      0.0007651000
_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  0.0609
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7561
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 572 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0423P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2062
_reflns_number_total             3031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06778d2.cif
_cod_data_source_block           b214-se
_cod_database_code               7127601
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.812
_shelx_estimated_absorpt_t_min   0.781
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C12(H12), C14(H14), C21(H21), C20(H20), C17(H17), C18(H18), C8(H8), C19(H19),
 C9(H9), C6(H6), C4(H4), C5(H5), C2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              55059
_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 1.782
_oxdiff_exptl_absorpt_empirical_full_min 0.480