Ortho-Hydroxylative ipso-Cyclization of N-arylpropiolamide.
Wang, Yu-Chao; Liu, Jin-Biao; Zhou, Hongwei; Rojsitthisak, Pornchai; Qiu, Guanyinsheng; Xie, Wenlin; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02590

data_4037678
_publ_section_title
;
 Ortho-Hydroxylative ipso-Cyclization of N-arylpropiolamide.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02590
_journal_year                    2019
_chemical_formula_sum            'C23 H18 Br N O3'
_chemical_formula_weight         436.29
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 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                 121.221(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9523(9)
_cell_length_b                   27.121(2)
_cell_length_c                   7.7458(6)
_cell_measurement_reflns_used    1692
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9360
_cell_measurement_theta_min      3.5050
_cell_volume                     1967.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4221
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    2.113
_exptl_absorpt_correction_T_max  0.713
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0380P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0658
_reflns_number_gt                2727
_reflns_number_total             2880
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02590_si_003.cif
_cod_data_source_block           dd
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               4037678