C-H Functionalization of azines. Anodic dehydroaromatization of 9-(hetero)aryl-9,10-dihydroacridines
Shchepochkin, Alexandr; Chupakhin, Oleg N.; Charushin, Valery; Steglenko, Dmitry; Minkin, Vladimir I.; Rusinov, Gennady; Matern, Anatoly; RSC Adv.  (2016) –; doi:10.1039/C6RA17783B

data_7226101
_publ_section_title
;
 C-H Functionalization of azines. Anodic dehydroaromatization of
 9-(hetero)aryl-9,10-dihydroacridines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA17783B
_journal_year                    2016
_chemical_formula_moiety         '2(C21 H16 F3 N)'
_chemical_formula_sum            'C42 H32 F6 N2'
_chemical_formula_weight         678.70
_chemical_name_systematic
10-Methyl-9-(4-trifluoromethylphenyl)-9,10-dihydroacridine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-11
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2016-05-12 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                109.830(2)
_cell_angle_beta                 111.959(3)
_cell_angle_gamma                90.014(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7236(3)
_cell_length_b                   12.3739(3)
_cell_length_c                   14.3134(4)
_cell_measurement_reflns_used    6027
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.6210
_cell_measurement_theta_min      2.0900
_cell_volume                     1639.37(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9999
_diffrn_measured_fraction_theta_max 0.8638
_diffrn_measurement_details
;
  1 omega  -20.00   20.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000 -150.0000 80

  2 omega  -14.00   16.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000  -90.0000 60

  3 omega  -84.00  -35.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -      -20.7920 -178.0000  120.0000 98

  4 omega  -21.00    9.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000   60.0000 60

  5 omega    4.00   91.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -       23.2920   57.0000 -180.0000 174

  6 omega   -2.00   96.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -       23.2920   38.0000   90.0000 196

  7 omega  -41.00   49.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -       23.2920  -38.0000  -90.0000 180
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0572071000
_diffrn_orient_matrix_UB_12      0.0079894000
_diffrn_orient_matrix_UB_13      0.0485140000
_diffrn_orient_matrix_UB_21      0.0319929000
_diffrn_orient_matrix_UB_22      -0.0385174000
_diffrn_orient_matrix_UB_23      -0.0302157000
_diffrn_orient_matrix_UB_31      0.0300046000
_diffrn_orient_matrix_UB_32      0.0473947000
_diffrn_orient_matrix_UB_33      -0.0054363000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16154
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         30.81
_diffrn_reflns_theta_min         1.77
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         8885
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0491
_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^)+(0.1200P)^2^+0.2100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1700
_reflns_number_gt                7301
_reflns_number_total             8885
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra17783b2.cif
_cod_data_source_block           exp_283
_cod_original_cell_volume        1639.36(8)
_cod_database_code               7226101
_chemical_oxdiff_formula         C10H10N
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_solvent_exptl_crystal_recrystallization_method ethanol