Palladium-Catalyzed Regioselective C–H Bond Arylations of Benzoxazoles and Benzothiazoles at the C7 Position
Abdellaoui, Fatma; Youssef, Chiraz; Ben Ammar, Hamed; Roisnel, Thierry; Soulé, Jean-François; Doucet, Henri; ACS Catalysis 6 (2016) 4248–; doi:10.1021/acscatal.6b00678

data_4513887
_publ_section_title
;
 Palladium-Catalyzed Regioselective C--H Bond Arylations of Benzoxazoles
 and Benzothiazoles at the C7 Position
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              4248
_journal_paper_doi               10.1021/acscatal.6b00678
_journal_volume                  6
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H13 N O2'
_chemical_formula_sum            'C20 H13 N O2'
_chemical_formula_weight         299.31
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2015-07-24T15:10:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.5615(19)
_cell_length_b                   11.966(3)
_cell_length_c                   21.750(5)
_cell_measurement_reflns_used    3611
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.03
_cell_measurement_theta_min      2.45
_cell_measurement_wavelength     0.71073
_cell_volume                     3009.0(11)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13645
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.03
_refine_ls_extinction_coef       0.0106(9)
_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   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.073
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.4421P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                2287
_reflns_number_total             3473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs6b00678_si_003.cif
_cod_data_source_block           M3JFS_FA80
_cod_depositor_comments          'Adding full bibliography for 4513887.cif.'
_cod_database_code               4513887