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_4032415
_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_absolute_configuration unk
_chemical_formula_moiety         'C14 H13 N1 O1'
_chemical_formula_sum            'C14 H13 N O'
_chemical_formula_weight         211.26
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-04
_audit_creation_method           CRYSTALS_ver_14.43
_audit_update_record
;
2016-08-05 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.44200(10)
_cell_length_b                   7.59210(10)
_cell_length_c                   21.9422(3)
_cell_measurement_reflns_used    9018
_cell_measurement_temperature    150
_cell_measurement_theta_max      73
_cell_measurement_theta_min      4
_cell_volume                     1073.16(3)
_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  0.040
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21129
_diffrn_reflns_theta_full        73.857
_diffrn_reflns_theta_max         73.857
_diffrn_reflns_theta_min         4.029
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro, Agilent Technologies, (2013), Yarnton, England 
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.15
_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     145
_refine_ls_number_reflns         2166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.0003909
_refine_ls_shift/su_mean         0.0000395
_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         0.0638
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0638
_reflns_limit_h_max              8
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                2114
_reflns_number_total             2166
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.45
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0364
_oxford_refine_ls_scale          8.69(16)
_oxford_reflns_number_all        2166
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'C:\Users\PaulCarr\Desktop\ban16_ At 16:50 on'
_publcif_datablock.id            {0ded5fb4-a402-4f51-b55f-3a8264551ddc}
_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_004.cif
_cod_data_source_block           ban16_pc18sn
_cod_depositor_comments
'Adding full bibliography for 4032415--4032418.cif.'
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C14 H13 N1 O1'
_cod_database_code               4032415