Multicomponent Synthesis of Diverse o-Arylated Benzamides via o-Aminophenol (OAP) Directed C(sp(2))-H Arylation.
Liu, Yunyun; Zhang, Yi; Wan, Jie-Ping; The Journal of organic chemistry 82 (2017) 8950–8957; doi:10.1021/acs.joc.7b01375

data_4032811
_publ_section_title
;
 Multicomponent Synthesis of Diverse o-Arylated Benzamides via
 o-Aminophenol (OAP) Directed C(sp(2))-H Arylation.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8950
_journal_page_last               8957
_journal_paper_doi               10.1021/acs.joc.7b01375
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C27 H23 N O2'
_chemical_formula_sum            'C27 H23 N O2'
_chemical_formula_weight         393.46
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_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                 99.67(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.181(2)
_cell_length_b                   11.283(2)
_cell_length_c                   18.953(4)
_cell_measurement_reflns_used    11293
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     2146.2(8)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       '\w 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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20001
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.05
_diffrn_standards_decay_%        0
_diffrn_standards_number         image
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+0.2310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                3249
_reflns_number_total             4883
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo7b01375_si_002.cif
_cod_data_source_block           shx97
_cod_original_cell_volume        2146.2(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4032811