Electrophilic Aromatic Substitutions of Aryltrifluoroborates with Retention of the BF3- Group: Quantification of the Activating and Directing Effects of the Trifluoroborate Group
Guillaume Berionni; Varvara Morozova; Maximilian Heininger; Peter Mayer; Paul Knochel; Herbert Mayr; Journal of the American Chemical Society 135 (2013) 6317–6324; doi:10.1021/ja4017655

data_4119646
_publ_contact_author_address
;
Department Chemie
Ludwig-Maximilians Universit\"at
Butenandtstra\&se 5-13 (Haus F)
D-81377 M\"unchen
Bundesrepublik Deutschland
;
_publ_contact_author_email       Herbert.Mayr@cup.uni-muenchen.de
_publ_contact_author_fax         '+49 89 2180 77717'
_publ_contact_author_name        'H. Mayr'
_publ_section_title
;
 Electrophilic Aromatic Substitutions of Aryltrifluoroborates with
 Retention of the BF3- Group: Quantification of the Activating and
 Directing Effects of the Trifluoroborate Group
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6317
_journal_page_last               6324
_journal_paper_doi               10.1021/ja4017655
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C12 H14 B F3 N2'
_chemical_formula_sum            'C12 H14 B F3 N2'
_chemical_formula_weight         254.059
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Peter Mayer'
_audit_block_code                C12H14BF3N2_qq029_mayr
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             25-Sep-12
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.5675(2)
_cell_length_b                   17.0840(5)
_cell_length_c                   21.3686(7)
_cell_measurement_reflns_used    116
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      20.5532
_cell_measurement_theta_min      3.4775
_cell_volume                     2397.54(13)
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Quest'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19230
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.45
_diffrn_reflns_theta_min         2.38
_diffrn_source_current           1
_diffrn_source_power             50
_diffrn_source_type              'Bruker I\mS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.40771(8)
_exptl_crystal_description       rod
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0533P)^2^+1.3097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                1777
_reflns_number_total             2183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4017655_si_002_4.cif
_cod_data_source_block           qq029
_cod_database_code               4119646