N-Cyanoimine as an electron-withdrawing functional group for organic semiconductors: example of dihydroindacenodithiophene positional isomers
Peltier, Jean-David; Heinrich, Benoît; Donnio, Bertrand; Jeannin, Olivier; Rault-Berthelot, Joëlle; Jacques, Emmanuel; Poriel, Cyril; Journal of Materials Chemistry C 6 (2018) 13197–; doi:10.1039/C8TC04313B

data_7237509
_publ_section_title
;
 N-Cyanoimine as an electron-withdrawing functional group for organic
 semiconductors: example of dihydroindacenodithiophene positional isomers
;
_journal_issue                   48
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              13197
_journal_paper_doi               10.1039/C8TC04313B
_journal_volume                  6
_journal_year                    2018
_chemical_formula_sum            'C30 H30 N4 S2'
_chemical_formula_weight         510.7
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2017-01-19T17:05:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-06-07 deposited with the CCDC.
2018-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                81.078(5)
_cell_angle_beta                 85.447(6)
_cell_angle_gamma                80.052(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0293(11)
_cell_length_b                   10.0818(13)
_cell_length_c                   18.972(3)
_cell_measurement_reflns_used    6801
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.78
_cell_measurement_wavelength     0.71073
_cell_volume                     1306.4(3)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.124655
_diffrn_orient_matrix_UB_12      0.002027
_diffrn_orient_matrix_UB_13      -0.029161
_diffrn_orient_matrix_UB_21      0.069828
_diffrn_orient_matrix_UB_22      -0.005183
_diffrn_orient_matrix_UB_23      0.044511
_diffrn_orient_matrix_UB_31      0.022525
_diffrn_orient_matrix_UB_32      -0.101611
_diffrn_orient_matrix_UB_33      0.004854
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1233
_diffrn_reflns_av_unetI/netI     0.1016
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27333
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.176
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.14
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0744P)^2^+0.5914P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1698
_reflns_Friedel_coverage         0
_reflns_number_gt                4187
_reflns_number_total             5978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc04313b2.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7237509
_shelx_res_checksum              64421
_shelx_hkl_checksum              45271