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_7226102
_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         'C20 H17 N'
_chemical_formula_sum            'C20 H17 N'
_chemical_formula_weight         271.35
_chemical_name_systematic        10-Methyl-9-phenyl-9,10-dihydroacridine
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-03
_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                90.00
_cell_angle_beta                 95.443(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.48181(13)
_cell_length_b                   10.7977(2)
_cell_length_c                   24.0126(6)
_cell_measurement_reflns_used    3104
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      32.1620
_cell_measurement_theta_min      2.5470
_cell_volume                     1414.92(6)
_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      120.01(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9071
_diffrn_measurement_details
;
  1 omega  -48.00   44.00   0.5000   14.4100
omega____ theta____ kappa____ phi______ frames
    -      -25.3885   38.0000 -150.0000 184

  2 omega -101.00  -43.00   0.5000   14.4100
omega____ theta____ kappa____ phi______ frames
    -      -25.3885 -178.0000  -60.0000 116

  3 omega  -89.00  -22.00   0.5000   14.4100
omega____ theta____ kappa____ phi______ frames
    -      -25.3885  -77.0000  -30.0000 134

  4 omega  -37.00   -1.00   0.5000   14.4100
omega____ theta____ kappa____ phi______ frames
    -       27.5760  -57.0000   90.0000 72
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0540075000
_diffrn_orient_matrix_UB_12      -0.0558792000
_diffrn_orient_matrix_UB_13      -0.0106594000
_diffrn_orient_matrix_UB_21      -0.0209161000
_diffrn_orient_matrix_UB_22      -0.0183122000
_diffrn_orient_matrix_UB_23      0.0275195000
_diffrn_orient_matrix_UB_31      -0.1163955000
_diffrn_orient_matrix_UB_32      0.0292168000
_diffrn_orient_matrix_UB_33      -0.0031170000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8836
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         32.46
_diffrn_reflns_theta_min         2.54
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83567
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_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         0.457
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                3830
_reflns_number_total             4628
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra17783b2.cif
_cod_data_source_block           exp_418
_cod_database_code               7226102
_chemical_oxdiff_formula         C10H10N
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_solvent_exptl_crystal_recrystallization_method ethanol