Regioselective C-H chalcogenylation and halogenation of arenes and alkenes under metal-free conditions.
Li, Bin; Hu, Mingli; Ge, Jun; Xu, Wei; Wu, Jinghan; Tong, Yao; Zhao, Zhengyi; Liu, Xiuxiu; He, Ling; Organic & biomolecular chemistry 21 (2023) 2910–2916; doi:10.1039/d3ob00150d

data_7159251
_publ_section_title
;
 Regioselective C-H chalcogenylation and halogenation of arenes and
 alkenes under metal-free conditions.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2910
_journal_page_last               2916
_journal_paper_doi               10.1039/d3ob00150d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H15 N O Se'
_chemical_formula_sum            'C16 H15 N O Se'
_chemical_formula_weight         316.25
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-01 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.420(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9417(14)
_cell_length_b                   7.4061(8)
_cell_length_c                   12.3726(14)
_cell_measurement_reflns_used    1206
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.7740
_cell_measurement_theta_min      3.3170
_cell_volume                     1393.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   20.00   82.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   57.0000  -30.0000 62

  2 omega   -6.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   77.0000   60.0000 91

  3 omega  -18.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336   38.0000 -150.0000 65

  4 omega  -73.00  -47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -57.0000   60.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0324046000
_diffrn_orient_matrix_UB_12      0.0046717000
_diffrn_orient_matrix_UB_13      -0.0286579000
_diffrn_orient_matrix_UB_21      0.0335006000
_diffrn_orient_matrix_UB_22      -0.0027659000
_diffrn_orient_matrix_UB_23      0.0526978000
_diffrn_orient_matrix_UB_31      0.0006476000
_diffrn_orient_matrix_UB_32      -0.0956698000
_diffrn_orient_matrix_UB_33      -0.0028641000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6701
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.059
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0366P)^2^+0.2315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1753
_reflns_number_total             2839
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00150d2.cif
_cod_data_source_block           220328_s1_lb
_cod_depositor_comments          'Adding full bibliography for 7159251.cif.'
_cod_database_code               7159251
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3se1
_shelx_estimated_absorpt_t_max   0.553
_shelx_estimated_absorpt_t_min   0.453
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16B,H16A)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
;
_shelx_res_checksum              3351
_olex2_submission_special_instructions 'No special instructions were received'