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_7131869
_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         'C24 H17 Cl N2'
_chemical_formula_sum            'C24 H17 Cl N2'
_chemical_formula_weight         368.84
_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             2023-03-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-17 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                97.410(5)
_cell_angle_beta                 109.977(6)
_cell_angle_gamma                103.615(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2175(6)
_cell_length_b                   10.4599(7)
_cell_length_c                   10.9144(7)
_cell_measurement_reflns_used    3351
_cell_measurement_temperature    233.01(10)
_cell_measurement_theta_max      74.8130
_cell_measurement_theta_min      4.4250
_cell_volume                     935.60(12)
_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 0.963
_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    -63.00  28.00   1.00    1.00    --  -40.50  57.00 -90.00   91
  2  \w    -74.00  28.00   1.00    1.00    --  -40.50  88.00   0.00  102
  3  \w   -109.00 -15.00   1.00    1.00    --  -40.50 -57.00 120.00   94
  4  \w     48.00  73.00   1.00    1.00    --   43.04 -77.00   0.00   25
  5  \w     31.00 106.00   1.00    1.00    --  108.30 -94.00 -60.00   75
  6  \w    114.00 140.00   1.00    1.00    --  108.30 -77.00 -60.00   26
  7  \w     40.00 112.00   1.00    1.00    --  108.30-125.00 150.00   72
  8  \w    112.00 147.00   1.00    1.00    --  108.30  77.00-120.00   35
  9  \w     74.00 111.00   1.00    1.00    --  108.30 -45.00  90.00   37
 10  \w     85.00 172.00   1.00    1.00    --  108.30  30.00   0.00   87
 11  \w     39.00 112.00   1.00    1.00    --  108.30-125.00 -90.00   73
 12  \w     35.00 132.00   1.00    1.00    --  108.30 -30.00 -60.00   97
 13  \w     99.00 173.00   1.00    1.00    --  108.30 125.00 -90.00   74
 14  \w     52.00  78.00   1.00    1.00    --  108.30-125.00 -60.00   26
 15  \w     47.00 106.00   1.00    1.00    --  108.30 -94.00   0.00   59
 16  \w    105.00 158.00   1.00    1.00    --  108.30  77.00  90.00   53
 17  \w    118.00 167.00   1.00    1.00    --  108.30  77.00  30.00   49
;
_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      0.0256560000
_diffrn_orient_matrix_UB_12      -0.1137467000
_diffrn_orient_matrix_UB_13      0.0739829000
_diffrn_orient_matrix_UB_21      -0.1435435000
_diffrn_orient_matrix_UB_22      -0.1028121000
_diffrn_orient_matrix_UB_23      -0.1179343000
_diffrn_orient_matrix_UB_31      0.1161316000
_diffrn_orient_matrix_UB_32      -0.0270147000
_diffrn_orient_matrix_UB_33      -0.0665197000
_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  0.0216
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6621
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.856
_diffrn_reflns_theta_min         4.428
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.871
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66232
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0028(4)
_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   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0482P)^2^+0.1324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2938
_reflns_number_total             3712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02968a2.cif
_cod_data_source_block           exp_18403cxl-450_auto
_cod_original_cell_volume        935.60(11)
_cod_database_code               7131869
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHONCl
_shelx_estimated_absorpt_t_max   0.835
_shelx_estimated_absorpt_t_min   0.400
_olex2_refinement_description
;
;
_shelx_res_checksum              89079
_shelx_hkl_checksum              11319
_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 1.492
_oxdiff_exptl_absorpt_empirical_full_min 0.672