Multifunctional Dithiadiazolyl Radicals: Fluorescence, Electroluminescence, and Photoconducting Behavior in Pyren-1'-yl-dithiadiazolyl.
Beldjoudi, Yassine; Nascimento, Mitchell A.; Cho, Yong Joo; Yu, Hyeonghwa; Aziz, Hany; Tonouchi, Daiki; Eguchi, Keitaro; Matsushita, Michio M.; Awaga, Kunio; Osorio-Roman, Igor; Constantinides, Christos P.; Rawson, Jeremy M.; Journal of the American Chemical Society 140 (2018) 6260–6270; doi:10.1021/jacs.7b12592

data_4131896
_publ_section_title
;
 Multifunctional Dithiadiazolyl Radicals: Fluorescence,
 Electroluminescence, and Photoconducting Behavior in
 Pyren-1'-yl-dithiadiazolyl.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6260
_journal_page_last               6270
_journal_paper_doi               10.1021/jacs.7b12592
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C17 H9 N2 S2'
_chemical_formula_sum            'C17 H9 N2 S2'
_chemical_formula_weight         305.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.7647(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3514(2)
_cell_length_b                   8.0601(2)
_cell_length_c                   21.3723(5)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      72.01
_cell_measurement_theta_min      4.15
_cell_volume                     1262.00(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II with Photon 100 CCD'
_diffrn_measurement_method       'phi and omegga scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17080
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        59.991
_diffrn_reflns_theta_max         59.991
_diffrn_reflns_theta_min         4.151
_diffrn_source                   'Cu micro-source, IuS'
_exptl_absorpt_coefficient_mu    3.747
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.13(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.6636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3371
_reflns_number_total             3711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b12592_si_002.cif
_cod_data_source_block           cu_YB038_0m_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4131896
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.439
_shelx_estimated_absorpt_t_max   0.893
_exptl_absorpt_special_details
;
sadabs 2016/2 Bruker AXS Madison WI, USA
;
_shelx_res_checksum              39491
_shelx_hkl_checksum              39120