A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A.
Yan, Qiao; Gin, Emma; Wasinska-Kalwa, Malgorzata; Banwell, Martin G.; Carr, Paul D.; The Journal of organic chemistry 82 (2017) 4148–4159; doi:10.1021/acs.joc.7b00044

data_4032463
_publ_section_title
;
 A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route
 to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine,
 Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4148
_journal_page_last               4159
_journal_paper_doi               10.1021/acs.joc.7b00044
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C14 H15 N O4'
_chemical_formula_weight         261.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-14
_audit_creation_method           'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_audit_update_record
;
2016-11-22 # Formatted by publCIF

;
_cell_angle_alpha                90.0
_cell_angle_beta                 104.596(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   21.5986(4)
_cell_length_b                   6.89910(11)
_cell_length_c                   17.6362(3)
_cell_measurement_reflns_used    13338
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.6710
_cell_measurement_theta_min      4.2310
_cell_volume                     2543.17(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'SHELXLE (C. B. H\"ubschle et al.,2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9903
_diffrn_measured_fraction_theta_max 0.9988
_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    -54.00  30.00   1.00    2.00    --  -37.04  57.00  60.00   84
  2  \w   -104.00 -20.00   1.00    2.00    --  -37.04 -57.00 -90.00   84
  3  \w      8.00 108.00   1.00    2.00    --   37.04  19.00  60.00  100
  4  \w     20.00 104.00   1.00    2.00    --   37.04  57.00 -90.00   84
  5  \w     18.00 106.00   1.00    2.00    --   37.04  38.00 120.00   88
  6  \w     23.00  90.00   1.00    2.00    --   37.04-125.00 -60.00   67
  7  \w     23.00  90.00   1.00    2.00    --   37.04-125.00-150.00   67
  8  \w    -31.00  64.00   1.00    2.00    --   37.04 -77.00 150.00   95
  9  \w     29.00  96.00   1.00    2.00    --   37.04-134.00  60.00   67
 10  \w    -30.00  54.00   1.00    2.00    --   37.04 -57.00  90.00   84
 11  \w    -34.00  66.00   1.00    2.00    --   37.04 -19.00 120.00  100
 12  \w      1.00  76.00   1.00    2.00    --   37.04 -99.00  60.00   75
 13  \w      1.00  76.00   1.00    2.00    --   37.04 -99.00-120.00   75
 14  \w    -30.00  54.00   1.00    2.00    --   37.04 -57.00 -60.00   84
 15  \w     18.00 106.00   1.00    2.00    --   37.04  38.00  30.00   88
 16  \w    -30.00  54.00   1.00    2.00    --   37.04 -57.00  60.00   84
 17  \w     42.00 130.00   1.00    6.00    --  111.00 -38.00-120.00   88
 18  \w     41.00 116.00   1.00    6.00    --  111.00-111.00  60.00   75
 19  \w     92.00 178.00   1.00    6.00    --  111.00  38.00 150.00   86
 20  \w     41.00 116.00   1.00    6.00    --  111.00-111.00 120.00   75
 21  \w     41.00 157.00   1.00    6.00    --  111.00 -12.00-120.00  116
 22  \w     86.00 178.00   1.00    6.00    --  111.00  25.00  60.00   92
 23  \w     43.00 138.00   1.00    6.00    --  111.00 -77.00 -90.00   95
 24  \w     43.00 138.00   1.00    6.00    --  111.00 -77.00  90.00   95
 25  \w     41.00 136.00   1.00    6.00    --  111.00 -25.00   0.00   95
 26  \w     41.00 116.00   1.00    6.00    --  111.00-111.00 -90.00   75
 27  \w     92.00 178.00   1.00    6.00    --  111.00  38.00  60.00   86
 28  \w     86.00 178.00   1.00    6.00    --  111.00  25.00 120.00   92
 29  \w    100.00 178.00   1.00    6.00    --  111.00 111.00 120.00   78
 30  \w     91.00 178.00   1.00    6.00    --  111.00  64.00-150.00   87
 31  \w     94.00 178.00   1.00    6.00    --  111.00  50.00-120.00   84
 32  \w     42.00 146.00   1.00    6.00    --  111.00 -92.00   0.00  104
 33  \w     41.00 136.00   1.00    6.00    --  111.00 -25.00-120.00   95
 34  \w     41.00 116.00   1.00    6.00    --  111.00-111.00-120.00   75
 35  \w     41.00 116.00   1.00    6.00    --  111.00-111.00   0.00   75
 36  \w     86.00 178.00   1.00    6.00    --  111.00  25.00 -60.00   92
 37  \w     42.00 130.00   1.00    6.00    --  111.00 -38.00  60.00   88
 38  \w     43.00 138.00   1.00    6.00    --  111.00 -77.00 150.00   95
 39  \w     41.00 116.00   1.00    6.00    --  111.00-111.00 -30.00   75
 40  \w     57.00 150.00   1.00    6.00    --  111.00 178.00   0.00   93
 41  \w     97.00 134.00   1.00    6.00    --  111.00  64.00  60.00   37
 42  \w    146.00 175.00   1.00    6.00    --  111.00  64.00  60.00   29
 43  \w    121.00 148.00   1.00    6.00    --  111.00  50.00  30.00   27
 44  \w     78.00 115.00   1.00    6.00    --  111.00-111.00 150.00   37
 45  \w     53.00 128.00   1.00    6.00    --  111.00 -50.00-180.00   75
 46  \w     44.00 101.00   1.00    6.00    --  111.00 -64.00   0.00   57
 47  \w     60.00 126.00   1.00    6.00    --  111.00 -50.00 120.00   66
 48  \w     97.00 178.00   1.00    6.00    --  111.00  12.00   0.00   81
 49  \w    131.00 158.00   1.00    6.00    --  111.00 111.00  30.00   27
 50  \w     97.00 178.00   1.00    6.00    --  111.00  50.00  90.00   81
 51  \w     44.00 118.00   1.00    6.00    --  111.00 -50.00   0.00   74
 52  \w     89.00 127.00   1.00    6.00    --  111.00 -64.00  30.00   38
 53  \w    104.00 131.00   1.00    6.00    --  111.00  25.00-120.00   27
 54  \w     78.00 105.00   1.00    6.00    --  111.00 -77.00   0.00   27
 55  \w     77.00 137.00   1.00    6.00    --  111.00 -77.00-120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0053018000
_diffrn_orient_matrix_UB_12      -0.2134897000
_diffrn_orient_matrix_UB_13      -0.0231852000
_diffrn_orient_matrix_UB_21      -0.0735418000
_diffrn_orient_matrix_UB_22      -0.0152401000
_diffrn_orient_matrix_UB_23      -0.0246670000
_diffrn_orient_matrix_UB_31      0.0001595000
_diffrn_orient_matrix_UB_32      0.0636952000
_diffrn_orient_matrix_UB_33      -0.0836413000
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            48482
_diffrn_reflns_theta_full        74.3338
_diffrn_reflns_theta_max         73.7519
_diffrn_reflns_theta_min         2.1137
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.836
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     206
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0842
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0677P)^2^+6.0311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2124
_refine_ls_wR_factor_ref         0.2142
_reflns_number_gt                4826
_reflns_number_total             5147
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {958c8754-fa53-4c34-8a6b-85d4f35d117f}
_cod_data_source_file            jo7b00044_si_007.cif
_cod_data_source_block           ban16_pc38sn
_cod_original_cell_volume        2543.16(8)
_cod_original_formula_sum        'C14 H15 N1 O4'
_cod_database_code               4032463
_chemical_oxdiff_formula         'c14 h15 n1 o4'