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_4104893
_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 H24 B2 F8 N4'
_chemical_formula_weight         482.04
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.1560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1713(2)
_cell_length_b                   10.9023(3)
_cell_length_c                   11.3064(3)
_cell_measurement_reflns_used    8489
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.48
_cell_measurement_theta_min      2.93
_cell_volume                     1112.79(5)
_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 0.815
_diffrn_measured_fraction_theta_max 0.815
_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  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11977
_diffrn_reflns_theta_full        35.77
_diffrn_reflns_theta_max         35.77
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9651
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      0
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         7231
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0571P)^2^+0.1447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                6915
_reflns_number_total             7231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903396e_si_002.cif
_cod_data_source_block           gb628_final
_cod_database_code               4104893