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_4032462
_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_moiety         'C13 H11 N1'
_chemical_formula_sum            'C13 H11 N'
_chemical_formula_weight         181.24
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-05
_audit_creation_method           CRYSTALS_ver_14.43
_audit_update_record
;
2016-08-05 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 98.458(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.3990(8)
_cell_length_b                   5.7846(2)
_cell_length_c                   7.8899(3)
_cell_measurement_reflns_used    7606
_cell_measurement_temperature    150
_cell_measurement_theta_max      74
_cell_measurement_theta_min      4
_cell_volume                     920.88(6)
_computing_cell_refinement
; 
 CrysAlisPro, Agilent Technologies, (2013), Yarnton, England 
;
_computing_data_collection       'SuperNova, (Agilent Technologies)'
_computing_data_reduction
; 
 CrysAlisPro, Agilent Technologies, (2013), Yarnton, England 
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16961
_diffrn_reflns_theta_full        73.874
_diffrn_reflns_theta_max         73.874
_diffrn_reflns_theta_min         2.190
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro, Agilent Technologies, (2013), Yarnton, England 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.0003060
_refine_ls_shift/su_mean         0.0000273
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Quasi-Unit weights 
 W = 1.0 or 1./2F 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0962
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0962
_reflns_limit_h_max              25
_reflns_limit_h_min              -25
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1748
_reflns_number_total             1858
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.14
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0586
_oxford_refine_ls_scale          9.0(3)
_oxford_reflns_number_all        1849
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'C:\Users\PaulCarr\Desktop\ban16_ At 10:36 on'
_publcif_datablock.id            {cb70610a-d2d7-4da0-8915-5c832f69bd8a}
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            jo7b00044_si_002.cif
_cod_data_source_block           ban16_pc19sn
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C13 H11 N1'
_cod_database_code               4032462