Ammonium Salt-Catalyzed Highly Practical Ortho-Selective Monohalogenation and Phenylselenation of Phenols: Scope and Applications
Xiong, Xiaodong; Yeung, Ying-Yeung; ACS Catalysis 8 (2018) 4033–; doi:10.1021/acscatal.8b00327

data_4515616
_publ_section_title
;
 Ammonium Salt-Catalyzed Highly Practical Ortho-Selective Monohalogenation
 and Phenylselenation of Phenols: Scope and Applications
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              4033
_journal_paper_doi               10.1021/acscatal.8b00327
_journal_volume                  8
_journal_year                    2018
_chemical_formula_sum            'C8 H6 Br Cl O3'
_chemical_formula_weight         265.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 93.138(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1058(4)
_cell_length_b                   17.9301(19)
_cell_length_c                   12.4296(15)
_cell_measurement_reflns_used    395
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     913.66(17)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16577
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.880
_diffrn_reflns_theta_min         2.272
_exptl_absorpt_coefficient_mu    4.759
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2931
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.279
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+5.7653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.1859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1742
_reflns_number_total             2170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b00327_si_012.cif
_cod_data_source_block           xxd268
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4515616
_shelx_estimated_absorpt_t_min   0.252
_shelx_estimated_absorpt_t_max   0.449
_shelxl_version_number           2014/6
_shelx_res_checksum              86563
_shelx_hkl_checksum              3234