Exocyclic Delocalization at the Expense of Aromaticity in 3,5-bis(π-Donor) Substituted Pyrazolium Ions and Corresponding Cyclic Bent Allenes
Israel Fernández; C. Adam Dyker; Alan DeHope; Bruno Donnadieu; Gernot Frenking; Guy Bertrand; Journal of the American Chemical Society 131 (2009) 11875–11881; doi:10.1021/ja903396e

data_4104892
_publ_section_title
;
 Exocyclic Delocalization at the Expense of Aromaticity in
 3,5-bis(\p-Donor) Substituted Pyrazolium Ions and Corresponding Cyclic
 Bent Allenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11875
_journal_page_last               11881
_journal_paper_doi               10.1021/ja903396e
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C19 H23 B F4 N4'
_chemical_formula_weight         394.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.826(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6443(4)
_cell_length_b                   16.8924(8)
_cell_length_c                   12.6854(6)
_cell_measurement_reflns_used    8860
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1967.43(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.716
_diffrn_measured_fraction_theta_max 0.716
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23816
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      0
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0776P)^2^+0.1445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                3941
_reflns_number_total             4895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903396e_si_001.cif
_cod_data_source_block           gb638_final
_cod_original_cell_volume        1967.43(15)
_cod_database_code               4104892