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_1555842
_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_formula_moiety         'C11 H20 N2'
_chemical_formula_sum            'C11 H20 N2'
_chemical_formula_weight         180.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date
;
'Mon Mar 31 19:49:59 2014'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_cell_angle_alpha                85.438(6)
_cell_angle_beta                 77.389(5)
_cell_angle_gamma                72.879(6)
_cell_formula_units_Z            2
_cell_length_a                   6.5009(3)
_cell_length_b                   8.0222(6)
_cell_length_c                   11.3792(7)
_cell_measurement_reflns_used    1812
_cell_measurement_temperature    253(2)
_cell_measurement_theta_max      73.4330
_cell_measurement_theta_min      5.7500
_cell_volume                     553.39(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      253(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
  1 omega  -62.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2864   57.0000  -30.0000 94

  2 omega  -93.00   -8.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2864  125.0000   60.0000 85

  3 omega -115.00  -21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2864  -38.0000 -180.0000 94

  4 omega   86.00  159.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501   30.0000  120.0000 73

  5 omega   47.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -94.0000  -90.0000 61

  6 omega   68.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -94.0000 -180.0000 37

  7 omega   35.00   81.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -30.0000  -90.0000 46

  8 omega   40.00   72.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -30.0000    0.0000 32

  9 omega   34.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -94.0000   30.0000 74

 10 omega   32.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -30.0000  150.0000 58

 11 omega   32.00  106.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -94.0000  120.0000 74

 12 omega   34.00   62.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -45.0000   90.0000 28

 13 omega   31.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -30.0000 -150.0000 59

 14 omega   81.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1501   45.0000 -180.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0978947000
_diffrn_orient_matrix_UB_12      0.0177154000
_diffrn_orient_matrix_UB_13      -0.1348925000
_diffrn_orient_matrix_UB_21      0.0481386000
_diffrn_orient_matrix_UB_22      0.1694024000
_diffrn_orient_matrix_UB_23      0.0246997000
_diffrn_orient_matrix_UB_31      0.2286345000
_diffrn_orient_matrix_UB_32      -0.1066663000
_diffrn_orient_matrix_UB_33      0.0211015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3110
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.560
_diffrn_reflns_theta_min         3.981
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.487
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_description
;
;
_exptl_crystal_F_000             200
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .06
_exptl_crystal_size_min          .03
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0743P)^2^+0.0482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1842
_reflns_number_total             2110
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02640_si_002.cif
_cod_data_source_block           ha66
_cod_original_cell_volume        553.38(6)
_cod_database_code               1555842
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 98.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C)
;