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_4119644
_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 H16 B F3 N2'
_chemical_formula_sum            'C12 H16 B F3 N2'
_chemical_formula_weight         256.075
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Mayer, P.'
_audit_block_code                C12H16BF3N2_pn299_mayr
_audit_creation_date             15-Sep-11
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             15-Sep-11
_cell_angle_alpha                90.00
_cell_angle_beta                 90.313(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.4163(11)
_cell_length_b                   5.8388(2)
_cell_length_c                   15.6465(7)
_cell_measurement_reflns_used    3787
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      3.134
_cell_volume                     2504.63(17)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_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      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0145020
_diffrn_orient_matrix_UB_12      0.0049119
_diffrn_orient_matrix_UB_13      -0.0584763
_diffrn_orient_matrix_UB_21      0.0334576
_diffrn_orient_matrix_UB_22      0.0022245
_diffrn_orient_matrix_UB_23      0.0257603
_diffrn_orient_matrix_UB_31      0.0008509
_diffrn_orient_matrix_UB_32      -0.1711832
_diffrn_orient_matrix_UB_33      -0.0013432
_diffrn_radiation_collimation    0.20
_diffrn_radiation_monochromator  'MONTEL, graded multilayered x-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6847
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         3.57
_diffrn_source_current           55.00
_diffrn_source_power             3.025
_diffrn_source_type              'FR 591 generator'
_diffrn_source_voltage           55.00
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.35822(9)
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0671
_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^)+(0.0759P)^2^+7.6558P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1745
_refine_ls_wR_factor_ref         0.1861
_reflns_number_gt                1807
_reflns_number_total             2276
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4017655_si_002_2.cif
_cod_data_source_block           pn299
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4119644