Regioselective Copper-Catalyzed Amination of Chlorobenzoic Acids: Synthesis and Solid-State Structures of N-Aryl Anthranilic Acid Derivatives
Xuefeng Mei; Adam T. August; Christian Wolf; Journal of Organic Chemistry 71 (2006) 142–149; doi:10.1021/jo0518809

data_4021364
_publ_section_title
;
 Regioselective Copper-Catalyzed Amination of Chlorobenzoic Acids:
 Synthesis and Solid-State Structures of
 N-Aryl Anthranilic Acid Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              142
_journal_page_last               149
_journal_paper_doi               10.1021/jo0518809
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C17 H19 N O2'
_chemical_formula_sum            'C17 H19 N O2'
_chemical_formula_weight         269.33
_chemical_name_common            'N-(2-tert-butylphenyl)anthranilic acid'
_chemical_name_systematic        'N-(2-tert-butylphenyl)anthranilic 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                106.582(3)
_cell_angle_beta                 91.207(3)
_cell_angle_gamma                99.212(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4748(12)
_cell_length_b                   9.3856(15)
_cell_length_c                   11.0319(17)
_cell_measurement_reflns_used    776
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.53
_cell_volume                     730.4(2)
_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 0.947
_diffrn_measured_fraction_theta_max 0.947
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6614
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0414
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.0990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2460
_reflns_number_total             3338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0518809si20050908_105012.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               4021364