Construction of Heteroacenes with Fused Thiophene and Pyrrole Rings via the Fischer Indolization Reaction.
Irgashev, Roman A.; Karmatsky, Arseny A.; Rusinov, Gennady L.; Charushin, Valery N.; Organic letters 18 (2016) 804–807; doi:10.1021/acs.orglett.6b00081

data_1542361
_publ_section_title
;
 Construction of Heteroacenes with Fused Thiophene and Pyrrole Rings via
 the Fischer Indolization Reaction.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              804
_journal_page_last               807
_journal_paper_doi               10.1021/acs.orglett.6b00081
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C23 H15 N S2'
_chemical_formula_sum            'C23 H15 N S2'
_chemical_formula_weight         369.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-18
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
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_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4216(6)
_cell_length_b                   5.8914(3)
_cell_length_c                   20.5783(10)
_cell_measurement_reflns_used    2661
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.6770
_cell_measurement_theta_min      2.8780
_cell_volume                     1719.99(14)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.8759
_diffrn_measurement_details
;
  1 omega  -46.00  -13.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360  -57.0000   60.0000 33

  2 omega    3.00   81.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   57.0000   30.0000 78

  3 omega    5.00   85.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   57.0000  -60.0000 80

  4 omega   15.00   47.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360  -77.0000 -180.0000 32
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0305788000
_diffrn_orient_matrix_UB_12      -0.0243746000
_diffrn_orient_matrix_UB_13      -0.0301745000
_diffrn_orient_matrix_UB_21      -0.0394433000
_diffrn_orient_matrix_UB_22      0.0099810000
_diffrn_orient_matrix_UB_23      0.0160579000
_diffrn_orient_matrix_UB_31      -0.0030302000
_diffrn_orient_matrix_UB_32      0.1175122000
_diffrn_orient_matrix_UB_33      -0.0076109000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8344
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.73
_diffrn_reflns_theta_min         2.87
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98564
_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    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0620P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                3683
_reflns_number_total             4683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00081_si_002.cif
_cod_data_source_block           exp_491
_cod_depositor_comments          'Adding full bibliography for 1542361.cif.'
_cod_original_cell_volume        1719.97(13)
_cod_database_code               1542361
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22