Effective modulation of the photoluminescence properties of 2,1,3-benzothiadiazoles and 2,1,3-benzoselenadiazoles by Pd-catalyzed C–H bond arylations
Idris, Imane; Tannoux, Thibault; Derridj, Fazia; Dorcet, Vincent; Boixel, Julien; Guerchais, Veronique; Soulé, Jean-François; Doucet, Henri; Journal of Materials Chemistry C 6 (2018) 1731–; doi:10.1039/C7TC05395A

data_7237048
_publ_section_title
;
 Effective modulation of the photoluminescence properties of
 2,1,3-benzothiadiazoles and 2,1,3-benzoselenadiazoles by Pd-catalyzed
 C--H bond arylations
;
_journal_issue                   7
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1731
_journal_paper_doi               10.1039/C7TC05395A
_journal_volume                  6
_journal_year                    2018
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H10 N2 S'
_chemical_formula_sum            'C16 H10 N2 S'
_chemical_formula_weight         262.32
_chemical_name_systematic
'4-(Naphthalen-2-yl)benzo[c][1,2,5]thiadiazole '
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2017-07-26 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.573(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   48.765(5)
_cell_length_b                   7.4625(8)
_cell_length_c                   7.0053(7)
_cell_measurement_reflns_used    7759
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.52
_cell_measurement_wavelength     0.71073
_cell_volume                     2532.5(5)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_limit_h_max       62
_diffrn_reflns_limit_h_min       -62
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.007
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: cyclohexane'
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.510
_exptl_crystal_size_min          0.140
_refine_diff_density_max         1.596
_refine_diff_density_min         -1.090
_refine_diff_density_rms         0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0763
_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^)+(0.1382P)^2^+1.2287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1899
_refine_ls_wR_factor_ref         0.2022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2425
_reflns_number_total             2908
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7tc05395a2.cif
_cod_data_source_block           IIR610
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7237048
_shelx_res_checksum              36845