Phenoxy-benzothiadiazole dyes: Synthesis, photophysical properties and preliminary application in OLEDs
Pazini, Alessandra; Maqueira, Luis; Avila, Harold C.; Valente, Felipe M.; Aderne, Rian E.; Back, Davi; Aucélio, Ricardo Q.; Cremona, Marco; Limberger, Jones; Tetrahedron Letters 59 (2018) 2994–2999; doi:10.1016/j.tetlet.2018.06.052

data_1566167
_publ_section_title
;
 Phenoxy-benzothiadiazole dyes: Synthesis, photophysical properties and
 preliminary application in OLEDs
;
_journal_issue                   31
_journal_name_full               'Tetrahedron Letters'
_journal_page_first              2994
_journal_page_last               2999
_journal_paper_doi               10.1016/j.tetlet.2018.06.052
_journal_volume                  59
_journal_year                    2018
_chemical_formula_moiety         'C20 H16 N2 O3 S'
_chemical_formula_sum            'C20 H16 N2 O3 S'
_chemical_formula_weight         364.41
_chemical_melting_point          383
_chemical_name_common
'methoxyphenoxy methoxyphenyl benzo thiadiazole'
_chemical_name_systematic
;
4-(4-methoxyphenoxy)-7-(4-methoxyphenyl)benzo[c][1,2,5]thiadiazole
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 101.2820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5330(4)
_cell_length_b                   36.5907(16)
_cell_length_c                   10.1464(4)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.308
_cell_measurement_theta_min      2.329
_cell_volume                     3470.9(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'
_computing_structure_refinement  'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2\% \f & \w scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.06
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            50563
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         2.25
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.04
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         8293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.104
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+1.0733P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.12
_reflns_number_gt                4989
_reflns_number_total             8293
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            Tetrahedron-Letters-2018-59-2994.cif
_cod_data_source_block           test3a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '383K' was changed to '383'
-- the value should be numeric and without a unit designator.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 

2022-03-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C40 H32 N4 O6 S2'
_cod_original_formula_weight         728.82
_cod_original_formula_moiety         'C40 H32 N4 O6 S2'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1566167