Regioselective Copper-Catalyzed Amination of Bromobenzoic Acids Using Aliphatic and Aromatic Amines
Christian Wolf; Shuanglong Liu; Xuefeng Mei; Adam T. August; Michael D. Casimir; Journal of Organic Chemistry 71 (2006) 3270–3273; doi:10.1021/jo060034a

data_4021630
_publ_section_title
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 Regioselective Copper-Catalyzed Amination of Bromobenzoic Acids
 Using Aliphatic and Aromatic Amines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3270
_journal_page_last               3273
_journal_paper_doi               10.1021/jo060034a
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C26 H22 N2 O3'
_chemical_formula_sum            'C26 H22 N2 O3'
_chemical_formula_weight         410.46
_chemical_name_common            'PYRENE AMINO ACID'
_chemical_name_systematic        'N-(1-pyrenyl)-2-aminobenzoic acid'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                65.18(4)
_cell_angle_beta                 79.23(4)
_cell_angle_gamma                69.25(4)
_cell_formula_units_Z            2
_cell_length_a                   8.367(5)
_cell_length_b                   11.281(7)
_cell_length_c                   13.200(5)
_cell_measurement_reflns_used    777
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.60
_cell_volume                     1056.5(10)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        SAINT,Bruker
_computing_molecular_graphics    'XSEED, L. Barbour (1999); http:\x-seed.net'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SMART platform CCD, Siemens/Bruker'
_diffrn_measurement_method       'omega scans'
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11312
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0720P)^2^+0.0612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                3121
_reflns_number_total             4593
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060034asi20060106_093543.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4021630