Transamination at the Crossroad of the One-Pot Synthesis of N-Substituted Quinonediimines and C-Substituted Benzobisimidazoles.
Andeme Edzang, Judicaelle; Chen, Zhongrui; Audi, Hassib; Canard, Gabriel; Siri, Olivier; Organic letters 18 (2016) 5340–5343; doi:10.1021/acs.orglett.6b02640

data_1555841
_publ_section_title
;
 Transamination at the Crossroad of the One-Pot Synthesis of N-Substituted
 Quinonediimines and C-Substituted Benzobisimidazoles.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5340
_journal_page_last               5343
_journal_paper_doi               10.1021/acs.orglett.6b02640
_journal_volume                  18
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H13 N2 O S'
_chemical_formula_sum            'C12 H13 N2 O S'
_chemical_formula_weight         233.3
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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   mixed
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2013-10-16T15:36:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.475(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8328(1)
_cell_length_b                   14.6676(3)
_cell_length_c                   14.1401(3)
_cell_measurement_reflns_used    10188
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      29.566
_cell_measurement_theta_min      2.045
_cell_measurement_wavelength     0.71073
_cell_volume                     1160.06(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10188
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         29.566
_diffrn_reflns_theta_min         2.045
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.3097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                2478
_reflns_number_total             3155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02640_si_003.cif
_cod_data_source_block           ha24
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555841
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.99