Dibenzo[f,h]furazano[3,4-b]quinoxalines: Synthesis by Intramolecular Cyclization through Direct Transition Metal-Free C‒H Functionalization and Electrochemical, Photophysical, and Charge Mobility Characterization
Kvashnin, Yuriy A.; Verbitskiy, Egor V.; Eltsov, Oleg S.; Slepukhin, Pavel A.; Tameev, Alexey R.; Nekrasova, Natalia V.; Rusinov, Gennady L.; Nunzi, Jean-Michel; Chupakhin, Oleg N.; Charushin, Valery N.; ACS Omega  (2020) –; doi:10.1021/acsomega.0c00479

data_4517535
_publ_section_title
;
 Dibenzo[f,h]furazano[3,4-b]quinoxalines: Synthesis by Intramolecular
 Cyclization through Direct Transition Metal-Free C--H Functionalization
 and Electrochemical, Photophysical, and Charge Mobility Characterization
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c00479
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H6 F2 N4 O'
_chemical_formula_sum            'C16 H6 F2 N4 O'
_chemical_formula_weight         308.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P -2n -2ac'
_space_group_name_H-M_alt        'P c 21 n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-02-14
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4950(6)
_cell_length_b                   13.8963(16)
_cell_length_c                   19.758(3)
_cell_measurement_reflns_used    1087
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.2890
_cell_measurement_theta_min      4.3730
_cell_volume                     1234.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9951
_diffrn_measured_fraction_theta_max 0.8748
_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     -7.00  18.00   1.00   40.00    --   22.21  83.00 -61.00   25
  2  \w     35.00  90.00   1.00   40.00    --   22.21  64.00-173.00   55
  3  \w    -64.00  -5.00   1.00   40.00    --  -23.93 -64.00  50.00   59
  4  \w    -99.00 -35.00   1.00   40.00    --  -23.93-178.00 150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0717077000
_diffrn_orient_matrix_UB_12      0.0182176000
_diffrn_orient_matrix_UB_13      -0.0293099000
_diffrn_orient_matrix_UB_21      -0.1179746000
_diffrn_orient_matrix_UB_22      -0.0332229000
_diffrn_orient_matrix_UB_23      0.0047410000
_diffrn_orient_matrix_UB_31      -0.0764417000
_diffrn_orient_matrix_UB_32      0.0341866000
_diffrn_orient_matrix_UB_33      0.0201857000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4636
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         3.58
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2961
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0801
_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^)+(0.1150P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1945
_refine_ls_wR_factor_ref         0.2399
_reflns_number_gt                1756
_reflns_number_total             2961
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao0c00479_si_002.cif
_cod_data_source_block           exp_21
_cod_database_code               4517535
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.743