Thieno[2,3-b]indole-Based Small Push-Pull Chromophores: Synthesis, Structure, and Electronic Properties.
Baert, François; Cabanetos, Clément; Allain, Magali; Silvestre, Virginie; Leriche, Philippe; Blanchard, Philippe; Organic letters 18 (2016) 1582–1585; doi:10.1021/acs.orglett.6b00438

data_1542994
_publ_section_title
;
 Thieno[2,3-b]indole-Based Small Push-Pull Chromophores: Synthesis,
 Structure, and Electronic Properties.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1582
_journal_page_last               1585
_journal_paper_doi               10.1021/acs.orglett.6b00438
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C15 H9 N3 S1'
_chemical_formula_sum            'C15 H9 N3 S'
_chemical_formula_weight         263.31
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-20T11:21:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                102.653(2)
_cell_angle_beta                 96.246(2)
_cell_angle_gamma                95.869(2)
_cell_formula_units_Z            4
_cell_length_a                   9.1174(2)
_cell_length_b                   11.1302(3)
_cell_length_c                   12.8185(3)
_cell_measurement_reflns_used    7998
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      76.112
_cell_measurement_theta_min      3.58
_cell_volume                     1250.97(5)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, V1.171.37.35g'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, V1.171.37.35g'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, V1.171.37.35g'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla and al., 2005)'
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector_area_resol_mean 5.199
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15823
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         76.88
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    2.188
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
        (compiled Dec  9 2014,15:38:47)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2093
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.0495
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.376
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.5246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                4552
_reflns_number_total             5157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00438_si_002.cif
_cod_data_source_block           fb076_150k
_cod_database_code               1542994