Temporary (P[double bond, length as m-dash]O) directing group enabled carbazole ortho arylation via palladium catalysis.
Qi, Zhi-Chao; Lou, Qin-Xin; Niu, Yuan; Yang, Shang-Dong; Chemical communications (Cambridge, England) 57 (2021) 2021–2024; doi:10.1039/d0cc07596e

data_7127827
_publ_section_title
;
 Temporary (P[double bond, length as m-dash]O) directing group enabled
 carbazole ortho arylation via palladium catalysis.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2021
_journal_page_last               2024
_journal_paper_doi               10.1039/d0cc07596e
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H15 N'
_chemical_formula_sum            'C19 H15 N'
_chemical_formula_weight         257.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-07-08 deposited with the CCDC.	2021-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7467(4)
_cell_length_b                   21.6002(5)
_cell_length_c                   7.8088(2)
_cell_measurement_reflns_used    1674
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.3260
_cell_measurement_theta_min      6.6770
_cell_volume                     2824.69(12)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_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     22.00  72.00   1.00    1.00    --    0.00  38.00   0.00   50
  2  \w     27.00  52.00   1.00    1.00    --   54.00  77.00  60.00   25
  3  \w     78.00 125.00   1.00    4.20    --  108.00  77.00 120.00   47
  4  \w    104.00 153.00   1.00    4.20    --  108.00 111.00 -60.00   49
  5  \w    131.00 175.00   1.00    4.20    --  108.00  63.00-180.00   44
  6  \w     82.00 125.00   1.00    4.20    --  108.00 -63.00-180.00   43
  7  \w     40.00  73.00   1.00    1.00    --   54.00 -57.00 -60.00   33
  8  \w     36.00 111.00   1.00    4.20    --  108.00-111.00 -60.00   75
  9  \w     60.00  93.00   1.00    4.20    --  108.00-111.00  60.00   33
 10  \w     16.00 127.00   1.00    1.00    --   54.00  19.00 -90.00  111
 11  \w    -24.00   5.00   1.00    1.00    --    0.00  38.00   0.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1832648000
_diffrn_orient_matrix_UB_12      0.0177372000
_diffrn_orient_matrix_UB_13      -0.0252482000
_diffrn_orient_matrix_UB_21      0.0220489000
_diffrn_orient_matrix_UB_22      -0.0639022000
_diffrn_orient_matrix_UB_23      -0.0396030000
_diffrn_orient_matrix_UB_31      -0.0695290000
_diffrn_orient_matrix_UB_32      0.0262961000
_diffrn_orient_matrix_UB_33      -0.0790904000
_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  0.0175
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2980
_diffrn_reflns_point_group_measured_fraction_full 0.743
_diffrn_reflns_point_group_measured_fraction_max 0.743
_diffrn_reflns_theta_full        66.570
_diffrn_reflns_theta_max         66.570
_diffrn_reflns_theta_min         4.093
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32467
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1857
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0734P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.374
_reflns_Friedel_fraction_full    0.440
_reflns_Friedel_fraction_max     0.440
_reflns_number_gt                1769
_reflns_number_total             1857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07596e2.cif
_cod_data_source_block           yuanzhichao_0430
_cod_depositor_comments          'Adding full bibliography for 7127827.cif.'
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               7127827
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N001(H001), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00K(H00D,H00K,H00L)
;
_shelx_res_checksum              57433
_olex2_date_sample_data_collection 2020-04-30
_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 4.121
_oxdiff_exptl_absorpt_empirical_full_min 0.436