C–N bond formation via Cu-catalyzed cross-coupling with boronic acids leading to methyl carbazole-3-carboxylate: synthesis of carbazole alkaloids
Rasheed, Sk.; Rao, D. Nageswar; Reddy, K. Ranjith; Aravinda, S.; Vishwakarma, Ram A.; Das, Parthasarathi; RSC Advances 4 (2014) 4960–; doi:10.1039/c3ra44903c

data_7239330
_publ_section_title
;
 C--N bond formation via Cu-catalyzed cross-coupling with boronic acids
 leading to methyl carbazole-3-carboxylate: synthesis of carbazole
 alkaloids
;
_journal_issue                   10
_journal_name_full               'RSC Advances'
_journal_page_first              4960
_journal_paper_doi               10.1039/c3ra44903c
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C17 H17 N1 O2'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.32
_chemical_name_systematic
;
methyl 6-propyl-9H-carbazole-3-carboxylate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.229(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8565(7)
_cell_length_b                   13.8210(7)
_cell_length_c                   8.0271(4)
_cell_measurement_reflns_used    4672
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      3.80
_cell_volume                     1411.65(13)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction,2010)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction,2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Xcalibur, sapphire3'
_diffrn_measurement_method       'omega scan'
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11900
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Crysalis PRO (Oxford Diffraction,2010)'
_exptl_crystal_colour            'color less'
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0752P)^2^+0.1975P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1561
_reflns_number_gt                1989
_reflns_number_total             3031
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra44903c.txt
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7239330