Base and ligand free copper-catalyzed N-arylation of 2-amino-N-heterocycles with boronic acids in air
Rao, D. Nageswar; Rasheed, Sk.; Aravinda, S.; Vishwakarma, Ram A.; Das, Parthasarathi; RSC Advances 3 (2013) 11472–; doi:10.1039/c3ra40735g

data_7238987
_publ_section_title
;
 Base and ligand free copper-catalyzed N-arylation of
 2-amino-N-heterocycles with boronic acids in air
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              11472
_journal_paper_doi               10.1039/c3ra40735g
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C16 H14 N2 O1'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_chemical_name_systematic
;
N-(4-methoxyphenyl)isoquinolin-1-amine
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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                 91.685(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4270(13)
_cell_length_b                   5.6126(5)
_cell_length_c                   16.7627(19)
_cell_measurement_reflns_used    1619
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      3.64
_cell_volume                     1262.7(2)
_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 0.951
_diffrn_measured_fraction_theta_max 0.951
_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  0.0650
_diffrn_reflns_av_sigmaI/netI    0.1505
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4561
_diffrn_reflns_theta_full        26.74
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_min         3.83
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Crysalis PRO (Oxford Diffraction,2010)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.2057
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0110P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                874
_reflns_number_total             2551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra40735g.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/n'
_cod_database_code               7238987