One Substrate, Two Modes of C-H Functionalization: A Metal-Controlled Site-Selectivity Switch in C-H Arylation Reactions.
Tiwari, Virendra Kumar; Kamal, Neha; Kapur, Manmohan; Organic letters 19 (2017) 262–265; doi:10.1021/acs.orglett.6b03558

data_1545230
_publ_section_title
;
 One Substrate, Two Modes of C-H Functionalization: A Metal-Controlled
 Site-Selectivity Switch in C-H Arylation Reactions.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              262
_journal_page_last               265
_journal_paper_doi               10.1021/acs.orglett.6b03558
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C17 H14 F N O'
_chemical_formula_weight         267.29
_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'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.204(4)
_cell_length_b                   16.267(5)
_cell_length_c                   7.421(2)
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.482
_cell_volume                     1352.5(7)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1241
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31550
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.949
_diffrn_reflns_theta_min         2.504
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .09
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0542
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1799
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2037
_reflns_number_total             3880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03558_si_002.cif
_cod_data_source_block           W1_a
_cod_original_cell_volume        1352.5(8)
_cod_database_code               1545230
_shelxl_version_number           2014/6
_shelx_res_checksum              73388
_shelx_hkl_checksum              82330