Direct access to functional phenazines via oxidative annulation of anilines and o-phenylenediamines with a reusable cobalt catalyst
Liu, Qingqing; Ci, Chenggang; Zhao, He; Xie, Rong; Jiang, HuanFeng; Zhang, Min; Green Chemistry 25 (2023) 678–683; doi:10.1039/D2GC03878A

data_7246068
_publ_section_title
;
 Direct access to functional phenazines via oxidative annulation of
 anilines and o-phenylenediamines with a reusable cobalt catalyst
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              678
_journal_page_last               683
_journal_paper_doi               10.1039/D2GC03878A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C17 H16 Cl N3'
_chemical_formula_sum            'C17 H16 Cl N3'
_chemical_formula_weight         297.78
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-15 deposited with the CCDC.	2022-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                68.667(17)
_cell_angle_beta                 79.026(15)
_cell_angle_gamma                72.896(16)
_cell_formula_units_Z            2
_cell_length_a                   6.7166(12)
_cell_length_b                   9.3699(17)
_cell_length_c                   12.656(2)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      70.9910
_cell_measurement_theta_min      3.7240
_cell_volume                     706.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.956
_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     41.00  80.00   1.00    1.00    --   40.73-128.00 153.00   39
  2  \w     41.00 122.00   1.00    1.50    --  107.58-125.00  60.00   81
  3  \w     67.00 107.00   1.00    1.50    --  107.58 -95.00 150.00   40
  4  \w     46.00 136.00   1.00    1.50    --  107.58 -61.00  30.00   90
  5  \w     84.00 174.00   1.00    1.50    --  107.58  30.00 -90.00   90
  6  \w    105.00 150.00   1.00    1.50    --  107.58 125.00 -60.00   45
  7  \w     97.00 132.00   1.00    1.50    --  107.58 143.00  37.00   35
  8  \w    145.00 175.00   1.00    1.50    --  107.58  61.00  90.00   30
  9  \w     94.00 126.00   1.00    1.50    --  107.58 125.00 -90.00   32
 10  \w     95.00 138.00   1.00    1.50    --  107.58 125.00-180.00   43
 11  \w     82.00 169.00   1.00    1.50    --  107.58  45.00   0.00   87
 12  \w     81.00 106.00   1.00    1.50    --  107.58  61.00  90.00   25
 13  \w     33.00 133.00   1.00    1.50    --  107.58 -77.00-150.00  100
 14  \w     47.00  94.00   1.00    1.00    --   40.73-125.00 -30.00   47
 15  \w     24.00  61.00   1.00    1.00    --   40.73-125.00-120.00   37
 16  \w   -109.00 -80.00   1.00    1.00    --  -40.73-143.00 -16.00   29
 17  \w   -115.00 -37.00   1.00    1.00    --  -40.73 -38.00 -90.00   78
 18  \w   -117.00   0.00   1.00    1.00    --  -40.73 -19.00 -30.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0161092000
_diffrn_orient_matrix_UB_12      0.0509991000
_diffrn_orient_matrix_UB_13      -0.1289569000
_diffrn_orient_matrix_UB_21      0.1540507000
_diffrn_orient_matrix_UB_22      0.1038549000
_diffrn_orient_matrix_UB_23      -0.0230672000
_diffrn_orient_matrix_UB_31      0.1846850000
_diffrn_orient_matrix_UB_32      -0.1406204000
_diffrn_orient_matrix_UB_33      -0.0080496000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4355
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.881
_diffrn_reflns_theta_min         3.766
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2737
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0670
_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^)+(0.0884P)^2^+0.1724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.1991
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1977
_reflns_number_total             2737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03878a2.cif
_cod_data_source_block           zw
_cod_depositor_comments          'Adding full bibliography for 7246068.cif.'
_cod_database_code               7246068
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.80
_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
2. Restrained distances
 C13-H13A = C13-H13B
 0.86 with sigma of 0.02
 C1-H1
 0.86 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C10(H10), C11(H11)
;
_shelx_res_checksum              77470
_olex2_date_sample_data_collection 2021-12-09
_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 1.993
_oxdiff_exptl_absorpt_empirical_full_min 0.516