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_4032464
_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         'C14 H11 N1 O2'
_chemical_formula_sum            'C14 H11 N O2'
_chemical_formula_weight         225.25
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-03
_audit_creation_method           CRYSTALS_ver_14.43
_audit_update_record
;
2016-08-03 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.13670(10)
_cell_length_b                   13.23900(10)
_cell_length_c                   22.5108(2)
_cell_measurement_reflns_used    22690
_cell_measurement_temperature    150
_cell_measurement_theta_max      74
_cell_measurement_theta_min      4
_cell_volume                     2126.88(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         MoK\a
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            40398
_diffrn_reflns_theta_full        73.869
_diffrn_reflns_theta_max         73.869
_diffrn_reflns_theta_min         3.927
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.91
_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    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.15
_refine_ls_extinction_coef       21.1(15)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.0007183
_refine_ls_shift/su_mean         0.0000725
_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         0.0578
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0578
_reflns_limit_h_max              8
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                2089
_reflns_number_total             2152
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.12
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0338
_oxford_refine_ls_scale          5.57(9)
_oxford_reflns_number_all        2152
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'C:\Users\PaulCarr\Desktop\ban16_ At 16:34 on'
_publcif_datablock.id            {8aae85f8-63ae-4fff-932d-984c1fe96e63}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE N   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 112,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'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_005.cif
_cod_data_source_block           ban16_pc16sn
_cod_original_sg_symbol_H-M      'P b c a '
_cod_original_formula_sum        'C14 H11 N1 O2'
_cod_database_code               4032464