Direct palladium-catalyzed ortho-arylation of benzylamines.
Lazareva, Anna; Daugulis, Olafs; Organic letters 8 (2006) 5211–5213; doi:10.1021/ol061919b

data_1506219
_publ_section_title
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 Direct palladium-catalyzed ortho-arylation of benzylamines.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5211
_journal_page_last               5213
_journal_paper_doi               10.1021/ol061919b
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C22 H19 Br2 N O'
_chemical_formula_weight         473.20
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 108.934(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3611(7)
_cell_length_b                   13.3819(7)
_cell_length_c                   12.5042(7)
_cell_measurement_reflns_used    5328
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      23.54
_cell_measurement_theta_min      2.30
_cell_volume                     1956.47(19)
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_structure_refinement  'SHELXL v5.10 (G.M. Sheldrick, 1997)'
_computing_structure_solution    'SHELXS v5.10 (G.M. Sheldrick, 1997)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 4K
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius APEX II CCD'
_diffrn_measurement_method       CCD
_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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8773
_diffrn_reflns_theta_full        23.54
_diffrn_reflns_theta_max         23.54
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    4.154
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.5089
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0207
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0325P)^2^+0.9430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0572
_reflns_number_gt                2387
_reflns_number_total             3051
_reflns_threshold_expression     >4sigma(I)
_cod_data_source_file            ol061919bsi20060802_072559.cif
_cod_data_source_block           k1032
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C22 H19 N O Br2'
_cod_database_code               1506219