Radical bromination-induced <i>ipso</i> cyclization-<i>ortho</i> cyclization sequence of <i>N</i>-hydroxylethyl-<i>N</i>-arylpropiolamides.
Wang, Yu-Chao; Huang, Keke; Lai, Xiaojing; Shi, Zhongning; Liu, Jin-Biao; Qiu, Guanyinsheng; Organic & biomolecular chemistry 19 (2021) 1940–1944; doi:10.1039/d1ob00010a

data_7157874
_publ_section_title
;
 Radical bromination-induced <i>ipso</i> cyclization-<i>ortho</i>
 cyclization sequence of
 <i>N</i>-hydroxylethyl-<i>N</i>-arylpropiolamides.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1940
_journal_page_last               1944
_journal_paper_doi               10.1039/d1ob00010a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C18 H16 Br N O2'
_chemical_formula_weight         358.23
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_audit_update_record
;
2020-12-11 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                87.116(6)
_cell_angle_beta                 69.183(7)
_cell_angle_gamma                70.272(7)
_cell_formula_units_Z            2
_cell_length_a                   8.9145(7)
_cell_length_b                   9.9325(8)
_cell_length_c                   10.1186(8)
_cell_measurement_reflns_used    1705
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4690
_cell_measurement_theta_min      3.8960
_cell_volume                     785.82(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0697
_diffrn_reflns_av_sigmaI/netI    0.0868
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5265
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    2.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.825
_refine_diff_density_min         -1.076
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_parameters     200
_refine_ls_number_reflns         2737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0568P)^2^+0.9012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1580
_reflns_number_gt                1905
_reflns_number_total             2737
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob00010a2.cif
_cod_data_source_block           201916-1
_cod_depositor_comments          'Adding full bibliography for 7157874.cif.'
_cod_original_cell_volume        785.82(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7157874