Direct formation of 4,5-disubstituted carbazoles via regioselective dilithiation.
Pocock, Ian A.; Alotaibi, Alya M.; Jagdev, Kesar; Prior, Connor; Burgess, Gregory R.; Male, Louise; Grainger, Richard S.; Chemical communications (Cambridge, England) 57 (2021) 7252–7255; doi:10.1039/d1cc02892h

data_7128575
_publ_section_title
;
 Direct formation of 4,5-disubstituted carbazoles via regioselective
 dilithiation.
;
_journal_issue                   59
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7252
_journal_page_last               7255
_journal_paper_doi               10.1039/d1cc02892h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C12 H7 N S2'
_chemical_formula_sum            'C12 H7 N S2'
_chemical_formula_weight         229.31
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-25 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                92.683(4)
_cell_angle_beta                 108.926(5)
_cell_angle_gamma                91.966(5)
_cell_formula_units_Z            4
_cell_length_a                   9.3372(6)
_cell_length_b                   10.5025(6)
_cell_length_c                   10.6156(6)
_cell_measurement_reflns_used    4334
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.4420
_cell_measurement_theta_min      4.1720
_cell_volume                     982.30(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_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   -113.00 -16.00   1.00    1.00    --  -42.56 -57.00 120.00   97
  2  \w    -86.00 -55.00   1.00    1.00    --  -42.56 125.00 -30.00   31
  3  \w    -65.00  30.00   1.00    1.00    --  -42.56  38.00  60.00   95
  4  \w    -61.00  25.00   1.00    1.00    --  -42.56  57.00 -90.00   86
  5  \w     40.00  65.00   1.00    1.89    --  106.63 -30.00  30.00   25
  6  \w     42.00 127.00   1.00    1.89    --  106.63 -30.00 -60.00   85
  7  \w     32.00 130.00   1.00    1.89    --  106.63 -30.00 120.00   98
  8  \w     36.00  86.00   1.00    1.89    --  106.63-125.00 120.00   50
  9  \w     36.00 130.00   1.00    1.89    --  106.63 -30.00-150.00   94
 10  \w     90.00 118.00   1.00    1.89    --  106.63-125.00 120.00   28
 11  \w    130.00 177.00   1.00    1.89    --  106.63  45.00 -90.00   47
 12  \w     95.00 123.00   1.00    1.89    --  106.63 -30.00  30.00   28
 13  \w     66.00 118.00   1.00    1.89    --  106.63-125.00 -90.00   52
 14  \w    143.00 175.00   1.00    1.89    --  106.63 125.00 150.00   32
 15  \w     98.00 123.00   1.00    1.89    --  106.63 125.00 150.00   25
 16  \w     40.00  94.00   1.00    1.89    --  106.63 -94.00-180.00   54
 17  \w    128.00 178.00   1.00    1.89    --  106.63 125.00-120.00   50
 18  \w     34.00 108.00   1.00    1.89    --  106.63 -77.00 -90.00   74
;
_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      -0.1436187000
_diffrn_orient_matrix_UB_12      0.0562210000
_diffrn_orient_matrix_UB_13      0.0163961000
_diffrn_orient_matrix_UB_21      0.0991179000
_diffrn_orient_matrix_UB_22      0.1018183000
_diffrn_orient_matrix_UB_23      0.1037296000
_diffrn_orient_matrix_UB_31      -0.0074735000
_diffrn_orient_matrix_UB_32      0.0899748000
_diffrn_orient_matrix_UB_33      -0.1122351000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6804
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.624
_diffrn_reflns_theta_min         4.220
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.559
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0371P)^2^+0.4707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3473
_reflns_number_total             3862
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02892h2.cif
_cod_data_source_block           10b
_cod_depositor_comments
'Adding full bibliography for 7128568--7128575.cif.'
_cod_original_cell_volume        982.30(10)
_cod_database_code               7128575
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H7 N1 S2'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C101(H101), C102(H102),
 C103(H103), C106(H106), C107(H107), C108(H108)
;
_shelx_res_checksum              57439
_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 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.810