Novel approach to biscarbazole alkaloids via Ullmann coupling - synthesis of murrastifoline-A and bismurrayafoline-A.
Börger, Carsten; Kataeva, Olga; Knölker, Hans-Joachim; Organic & biomolecular chemistry 10 (2012) 7269–7273; doi:10.1039/c2ob26229k

data_7152600
_publ_section_title
;
 Novel approach to biscarbazole alkaloids via Ullmann coupling - synthesis
 of murrastifoline-A and bismurrayafoline-A.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7269
_journal_page_last               7273
_journal_paper_doi               10.1039/c2ob26229k
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C19 H20 Br N O3'
_chemical_formula_sum            'C19 H20 Br N O3'
_chemical_formula_weight         390.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.586(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8228(3)
_cell_length_b                   20.4039(7)
_cell_length_c                   9.9068(4)
_cell_measurement_reflns_used    4936
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.37
_cell_volume                     1709.21(11)
_computing_cell_refinement       'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)'
_computing_data_collection       'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)'
_computing_data_reduction        'SAINT NT v6.0 (Bruker AXS, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)'
_computing_structure_solution    'Sheldrick, G. M. SHELXS-97.1990.'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'Bruker Kappa APEX II CCD'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '0.5 deg frames in phi and omega'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20882
_diffrn_reflns_theta_full        28.48
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    2.422
_exptl_absorpt_correction_T_max  0.9309
_exptl_absorpt_correction_T_min  0.5717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0318P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0733
_reflns_number_gt                2950
_reflns_number_total             4197
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26229k.txt
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7152600