A 6π + 6π Potentially Antiaromatic Zwitterion Preferred to a Quinoidal Structure: Its Reactivity Toward Organic and Inorganic Reagents
Pierre Braunstein; Olivier Siri; Jean-philippe Taquet; Marie-Madeleine Rohmer; Marc Bénard; Richard Welter; Journal of the American Chemical Society 125 (2003) 12246–12256; doi:10.1021/ja0354622

data_4114223
_publ_contact_author_address
;
Institut Le Bel, rue Blaise Pascal, 67000 STRASBOURG, FRANCE
;
_publ_contact_author_email       bruanst@chimie.u-strasbg.fr
_publ_contact_author_fax         0390241322
_publ_contact_author_name
;
Pierre Braunstein
;
_publ_contact_author_phone       0390241308
_publ_section_title
;
 A 6\p + 6\p Potentially Antiaromatic Zwitterion Preferred to a Quinoidal
 Structure: Its Reactivity Toward Organic and Inorganic Reagents
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12246
_journal_page_last               12256
_journal_paper_doi               10.1021/ja0354622
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C18 H31 B Cl2 F4 N2 O2'
_chemical_formula_sum            'C18 H31 B Cl2 F4 N2 O2'
_chemical_formula_weight         465.16
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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_creation_date             10-11-00
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(10)
_cell_angle_beta                 116.35(5)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            16
_cell_length_a                   32.358(2)
_cell_length_b                   13.502(2)
_cell_length_c                   24.127(2)
_cell_measurement_reflns_used    35013
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     9446(4)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'ATOMS V6 (Dowty, 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\p scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.2436
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10505
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prism
_exptl_crystal_F_000             3904
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.00032(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.323
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         10504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.323
_refine_ls_R_factor_all          0.3036
_refine_ls_R_factor_gt           0.1325
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2118
_refine_ls_wR_factor_ref         0.2480
_reflns_number_gt                3649
_reflns_number_total             10504
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0354622si20030618_081901.cif
_cod_data_source_block           siri
_cod_original_cell_volume        9445.8(17)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4114223