Ring-fused dimethoxybenzimidazole-benzimidazolequinone (DMBBQ): tunable halogenation and quinone formation using NaX/Oxone.
Conboy, Darren; Kielty, Patrick; Bear, Joseph C.; Cockcroft, Jeremy K.; Farràs, Pau; McArdle, Patrick; Singer, Richard J.; Smith, Dennis A.; Aldabbagh, Fawaz; Organic & biomolecular chemistry 19 (2021) 2716–2724; doi:10.1039/d1ob00032b

data_7157909
_publ_section_title
;
 Ring-fused dimethoxybenzimidazole-benzimidazolequinone (DMBBQ): tunable
 halogenation and quinone formation using NaX/Oxone.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2716
_journal_page_last               2724
_journal_paper_doi               10.1039/d1ob00032b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C25 H22 Cl F3 N4 O4'
_chemical_formula_sum            'C25 H22 Cl F3 N4 O4'
_chemical_formula_weight         534.91
_chemical_name_systematic
8''-chloro-6'',9''-dimethoxy-8-(trifluoromethyl)-[7,7''-bipyrido[1,2-a]benzimidazole]-6,9-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-07 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.382(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9129(3)
_cell_length_b                   16.4330(2)
_cell_length_c                   8.5648(2)
_cell_measurement_reflns_used    19262
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.4870
_cell_measurement_theta_min      5.3600
_cell_volume                     2305.81(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.76a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -5.00  20.00   1.00    1.00    --   34.00  94.00-102.97   25
  2  \w     -4.00  21.00   1.00    1.00    --   34.00  91.00  94.18   25
  3  \w      2.00  27.00   1.00    1.00    --   38.00  87.00 -41.98   25
  4  \w   -116.00 -31.00   1.00    1.00    --  -42.62 -38.00 -90.00   85
  5  \w   -117.00 -18.00   1.00    1.00    --  -42.62 -38.00   0.00   99
  6  \w   -105.00 -79.00   1.00    1.00    --  -42.62 -38.00  90.00   26
  7  \w    -71.00  31.00   1.00    1.00    --  -42.62  57.00  60.00  102
  8  \w    -56.00 -20.00   1.00    1.00    --  -42.62 -38.00  90.00   36
  9  \w     -2.00  70.00   1.00    1.00    --   42.62 -57.00-150.00   72
 10  \w     28.00  99.00   1.00    1.00    --   42.62-125.00-180.00   71
 11  \w     10.00  35.00   1.00    1.00    --   42.62  75.00-175.24   25
 12  \w     13.00  41.00   1.00    1.00    --   46.00  79.00  19.71   28
 13  \w     15.00  41.00   1.00    1.00    --   46.00  76.00 115.71   26
 14  \w     13.00  38.00   1.00    1.00    --   46.00  79.00-158.99   25
 15  \w     31.00  58.00   1.00    1.00    --   62.00  72.00 121.42   27
 16  \w     30.00  57.00   1.00    1.00    --   62.00  74.00 172.16   27
 17  \w     34.00  60.00   1.00    1.00    --   66.00  74.00 -63.53   26
 18  \w    101.00 128.00   1.00    1.00    --   66.00  74.00 -63.53   27
 19  \w     34.00  60.00   1.00    1.00    --   66.00  73.00  51.69   26
 20  \w     34.00  66.00   1.00    1.00    --   66.00  74.00-126.71   32
 21  \w     39.00  76.00   1.00    1.00    --   70.00  72.00-155.86   37
 22  \w     39.00  65.00   1.00    1.00    --   70.00  70.00   5.25   26
 23  \w     39.00  65.00   1.00    1.00    --   70.00  70.00 -29.42   26
 24  \w     42.00  76.00   1.00    2.00    --   74.00  74.00-112.73   34
 25  \w     42.00  68.00   1.00    2.00    --   74.00  73.00  58.36   26
 26  \w     42.00  68.00   1.00    2.00    --   74.00  74.00  73.45   26
 27  \w     48.00  74.00   1.00    2.00    --   78.00  68.00 136.26   26
 28  \w     50.00  76.00   1.00    2.00    --   78.00  55.00 133.81   26
 29  \w     52.00  77.00   1.00    2.00    --   82.00  72.00   1.43   25
 30  \w     52.00  81.00   1.00    2.00    --   82.00  66.00 -51.22   29
 31  \w     54.00  89.00   1.00    2.00    --   86.00  74.00 152.90   35
 32  \w     61.00  87.00   1.00    2.00    --   90.00  59.00  63.16   26
 33  \w    116.00 163.00   1.00    2.00    --   90.00  66.00  68.67   47
 34  \w     60.00  87.00   1.00    2.00    --   90.00  66.00  68.67   27
 35  \w     63.00  96.00   1.00    2.00    --   90.00  64.00-130.15   33
 36  \w     59.00  85.00   1.00    2.00    --   90.00  69.00 128.32   26
 37  \w     69.00 166.00   1.00    2.00    --   98.00  59.00  28.51   97
 38  \w     73.00 173.00   1.00    2.00    --  104.49  74.00-109.40  100
 39  \w     37.00 107.00   1.00    2.00    --  104.49-100.00 -25.87   70
 40  \w     75.00 155.00   1.00    2.00    --  104.49  61.00   0.00   80
 41  \w     83.00 164.00   1.00    2.00    --  104.49  61.00-150.00   81
 42  \w     77.00 141.00   1.00    2.00    --  104.49  70.00 -26.66   64
 43  \w     73.00 174.00   1.00    2.00    --  104.49  73.00 176.99  101
 44  \w     76.00 115.00   1.00    2.00    --  104.49  61.00-180.00   39
 45  \w     75.00 124.00   1.00    2.00    --  104.49  61.00 150.00   49
 46  \w    130.00 163.00   1.00    2.00    --  104.49 125.00 150.00   33
 47  \w     75.00 101.00   1.00    2.00    --  104.49  63.00 -42.93   26
 48  \w    108.00 176.00   1.00    2.00    --  104.49  61.00 -60.00   68
 49  \w    140.00 173.00   1.00    2.00    --  104.49  69.00  71.50   33
 50  \w     75.00 103.00   1.00    2.00    --  104.49  61.00 -60.00   28
 51  \w     74.00 129.00   1.00    2.00    --  104.49  69.00  71.50   55
 52  \w     82.00 177.00   1.00    2.00    --  104.49  45.00 120.00   95
 53  \w     55.00 112.00   1.00    2.00    --  104.49 -45.00 120.00   57
 54  \w     97.00 148.00   1.00    2.00    --  104.49 125.00 120.00   51
 55  \w     32.00 111.00   1.00    2.00    --  104.49-125.00 -60.00   79
 56  \w     41.00 111.00   1.00    2.00    --  104.49-125.00 120.00   70
 57  \w     39.00 103.00   1.00    2.00    --  104.49 -94.00 150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0268006000
_diffrn_orient_matrix_UB_12      0.0859443000
_diffrn_orient_matrix_UB_13      -0.0374313000
_diffrn_orient_matrix_UB_21      -0.0797126000
_diffrn_orient_matrix_UB_22      0.0097730000
_diffrn_orient_matrix_UB_23      -0.1326797000
_diffrn_orient_matrix_UB_31      -0.0420763000
_diffrn_orient_matrix_UB_32      0.0362288000
_diffrn_orient_matrix_UB_33      0.1243315000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            38841
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.692
_diffrn_reflns_theta_min         3.810
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.065
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.76a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         4551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+1.6916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4063
_reflns_number_total             4551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00032b2.cif
_cod_data_source_block           exp_2141
_cod_depositor_comments
'Adding full bibliography for 7157908--7157910.cif.'
_cod_database_code               7157909
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C25 H22 Cl1 F3 N4 O4 '
_chemical_oxdiff_usercomment     'DC035E: Dark Orange Crystal Cut from Lump'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
;
_shelx_res_checksum              71061
_olex2_date_sample_data_collection 2020-02-11
_olex2_exptl_crystal_mounting_method
'Crystal cut from large lump and mounted on a Hampton Research 20um nyloon loop (0.3mm diameter) and cooled from 295K to 100K'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.841