Reagent control enables selective and regiodivergent opening of unsymmetrical phenonium ions.
Xu, Shiyan; Holst, Hannah Marie; McGuire, Shelby Barbara; Race, Nicholas James; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c02095

data_4134791
_publ_section_title
;
 Reagent control enables selective and regiodivergent opening of
 unsymmetrical phenonium ions.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02095
_journal_year                    2020
_chemical_formula_moiety         'C12 H14 Cl F3 O'
_chemical_formula_sum            'C12 H14 Cl F3 O'
_chemical_formula_weight         266.68
_chemical_name_common            20006z
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.0407(10)
_cell_length_b                   12.4313(7)
_cell_length_c                   5.1226(2)
_cell_measurement_reflns_used    2952
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.61
_cell_volume                     1276.20(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-AXS VENTURE PHOTON-III'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            11767
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.393
_diffrn_reflns_theta_min         2.611
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       Needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6274
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1150 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3189
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0429P)^2^+0.3893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2861
_reflns_number_total             3189
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02095_si_003.cif
_cod_data_source_block           20006z
_cod_database_code               4134791
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              51928
_shelx_hkl_checksum              78042