Electrophilicities of Benzaldehyde-Derived Iminium Ions: Quantification of the Electrophilic Activation of Aldehydes by Iminium Formation
Roland Appel; Saloua Chelli; Takahiro Tokuyasu; Konstantin Troshin; Herbert Mayr; Journal of the American Chemical Society 135 (2013) 6579–6587; doi:10.1021/ja401106x

data_4119679
_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
;
 Electrophilicities of Benzaldehyde-Derived Iminium Ions: Quantification
 of the Electrophilic Activation of Aldehydes by Iminium Formation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6579
_journal_page_last               6587
_journal_paper_doi               10.1021/ja401106x
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C13 H16 F3 N O2'
_chemical_formula_sum            'C13 H16 F3 N O2'
_chemical_formula_weight         275.267
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Peter Mayer'
_audit_block_code                C13H16F3NO2_rv113_mayr
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             05-Apr-13
_cell_angle_alpha                90.00
_cell_angle_beta                 102.2327(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.4884(2)
_cell_length_b                   34.9745(9)
_cell_length_c                   9.4939(3)
_cell_measurement_reflns_used    121
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      19.7702
_cell_measurement_theta_min      3.1527
_cell_volume                     2754.53(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      173(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Venture'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_collimation    0.8_mm
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            48690
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.98
_diffrn_source_current           50
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_correction_T_min  0.9149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.32755(6)
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4855
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0862
_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^)+(0.0559P)^2^+8.0194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.2053
_reflns_number_gt                3651
_reflns_number_total             4855
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja401106x_si_002.cif
_cod_data_source_block           rv113
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4119679