A transition metal- and photosensitizer-free approach for site-selective (hetero)arylation of polychlorinated heteroarenes
Cheng, Xiuliang; He, Yuhang; Song, Silin; Lin, Yu-Mei; Gong, Lei; Chemical Communications  (2023) –; doi:10.1039/D3CC02968A

data_7131872
_publ_section_title
;
 A transition metal- and photosensitizer-free approach for site-selective
 (hetero)arylation of polychlorinated heteroarenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02968A
_journal_year                    2023
_chemical_formula_moiety         'C23 H14 Cl2 N2'
_chemical_formula_sum            'C23 H14 Cl2 N2'
_chemical_formula_weight         389.26
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-06
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-06 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                84.887(4)
_cell_angle_beta                 64.323(5)
_cell_angle_gamma                82.321(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3919(5)
_cell_length_b                   10.1672(5)
_cell_length_c                   10.7498(5)
_cell_measurement_reflns_used    3819
_cell_measurement_temperature    233.01(10)
_cell_measurement_theta_max      76.2750
_cell_measurement_theta_min      4.3750
_cell_volume                     916.27(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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      233.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_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    -66.00  25.00   1.00    1.00    --  -40.50  57.00 120.00   91
  2  \w   -110.00 -18.00   1.00    1.00    --  -40.50 -37.00-180.00   92
  3  \w    -63.00  32.00   1.00    1.00    --  -40.50  37.00   0.00   95
  4  \w     21.00  48.00   1.00    1.00    --   43.04 -99.00  90.00   27
  5  \w     57.00  93.00   1.00    1.00    --   43.04-125.00   0.00   36
  6  \w     43.00  74.00   1.00    1.00    --   43.04-125.00-150.00   31
  7  \w     30.00 104.00   1.00    2.11    --  111.00 -94.00  90.00   74
  8  \w     55.00 133.00   1.00    2.11    --  111.00 -45.00 -90.00   78
  9  \w    104.00 138.00   1.00    2.11    --  111.00  77.00 120.00   34
 10  \w     58.00 134.00   1.00    2.11    --  111.00 -45.00  30.00   76
 11  \w     92.00 135.00   1.00    2.11    --  111.00 -45.00-180.00   43
 12  \w     46.00 107.00   1.00    2.11    --  111.00 -94.00 -90.00   61
 13  \w     42.00  77.00   1.00    2.11    --  111.00 -45.00-180.00   35
 14  \w     65.00 105.00   1.00    2.11    --  111.00 -94.00   0.00   40
 15  \w    105.00 173.00   1.00    2.11    --  111.00  77.00 -30.00   68
 16  \w     74.00 131.00   1.00    2.11    --  111.00  15.00  90.00   57
 17  \w     68.00  94.00   1.00    2.11    --  111.00-125.00-150.00   26
 18  \w     92.00 163.00   1.00    2.11    --  111.00  45.00 -90.00   71
 19  \w     66.00 112.00   1.00    2.11    --  111.00-125.00-120.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0439287000
_diffrn_orient_matrix_UB_12      0.1113076000
_diffrn_orient_matrix_UB_13      -0.0882212000
_diffrn_orient_matrix_UB_21      -0.1407736000
_diffrn_orient_matrix_UB_22      -0.0722848000
_diffrn_orient_matrix_UB_23      0.0144795000
_diffrn_orient_matrix_UB_31      -0.1084132000
_diffrn_orient_matrix_UB_32      0.0760955000
_diffrn_orient_matrix_UB_33      0.1316186000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6326
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.068
_diffrn_reflns_theta_min         4.391
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0447P)^2^+0.1296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3120
_reflns_number_total             3678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02968a2.cif
_cod_data_source_block           exp_18506_auto
_cod_database_code               7131872
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHONCl
_olex2_refinement_description
;
;
_shelx_res_checksum              63363
_shelx_hkl_checksum              58540
_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 1.209
_oxdiff_exptl_absorpt_empirical_full_min 0.869