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_4515623
_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            'C12 H10 Br2 Cl2 O4'
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_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 91.5018(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.7811(17)
_cell_length_b                   3.9260(2)
_cell_length_c                   21.7084(12)
_cell_measurement_reflns_used    410
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     2792.9(3)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
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_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
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_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24700
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         2.224
_exptl_absorpt_coefficient_mu    6.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3263
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.135
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         2.270
_refine_diff_density_min         -1.111
_refine_diff_density_rms         0.194
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0615
_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^)+(0.1359P)^2^+42.0633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1967
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                2340
_reflns_number_total             2516
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           xxd2199
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4515623
_shelx_estimated_absorpt_t_min   0.148
_shelx_estimated_absorpt_t_max   0.370
_shelxl_version_number           2014/6
_shelx_res_checksum              21242
_shelx_hkl_checksum              2866