Carbon Nucleophilicities of Indoles in SNAr Substitutions of Superelectrophilic 7-Chloro-4,6-dinitrobenzofuroxan and -benzofurazan
Pedro Rodriguez-Dafonte; François Terrier; Sami Lakhdar; Sergei Kurbatov; Régis Goumont; Journal of Organic Chemistry 74 (2009) 3305–3315; doi:10.1021/jo900076r

data_4024487
_publ_contact_author
;
Francois Terrier
;
_publ_contact_author_email       terrier@chimie.uvsq.fr
_publ_contact_author_fax         '00 33 1 39 25 44 52'
_publ_contact_author_phone       '00 33 1 39 25 44 50'
_publ_section_title
;
Carbon Nucleophilicities of Indoles in SNAr Substitutions of
Superelectrophilic 7-Chloro-4,6-dinitrobenzofuroxan and -benzofurazan
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3305
_journal_page_last               3315
_journal_paper_doi               10.1021/jo900076r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C22 H15 N5 O6'
_chemical_formula_sum            'C22 H15 N5 O6'
_chemical_formula_weight         445.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.44(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.957(4)
_cell_length_b                   24.80(3)
_cell_length_c                   10.408(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19
_cell_measurement_theta_min      2
_cell_volume                     1970(4)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0778
_diffrn_reflns_av_sigmaI/netI    0.1022
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10658
_diffrn_reflns_theta_full        24.92
_diffrn_reflns_theta_max         24.92
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0621P)^2^+0.0637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                1809
_reflns_number_total             3337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900076r_si_002.cif
_cod_data_source_block           sk10-3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024487