#------------------------------------------------------------------------------
#$Date: 2022-03-18 12:32:04 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273808 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/61/1566167.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1566167
loop_
_publ_author_name
'Pazini, Alessandra'
'Maqueira, Luis'
'Avila, Harold C.'
'Valente, Felipe M.'
'Aderne, Rian E.'
'Back, Davi'
'Aucélio, Ricardo Q.'
'Cremona, Marco'
'Limberger, Jones'
_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° φ & ω 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/[σ²(Fo²)+(0.0478P)²+1.0733P] where P=(Fo²+2Fc²)/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     >2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.04015(6) 0.611943(16) 1.38701(5) 0.05436(16) Uani 1 1 d . . .
S1 S 0.47406(7) 0.412008(17) -0.34084(6) 0.05930(18) Uani 1 1 d . . .
O2A O 0.26401(17) 0.71433(4) 1.35501(14) 0.0578(4) Uani 1 1 d . . .
O2 O 0.23441(18) 0.31076(4) -0.33387(14) 0.0596(4) Uani 1 1 d . . .
O3 O 0.38567(16) 0.50809(4) 0.34914(15) 0.0597(4) Uani 1 1 d . . .
O3A O 0.12468(17) 0.51219(4) 0.69923(15) 0.0569(4) Uani 1 1 d . . .
O1 O 0.06193(17) 0.16965(4) -0.26083(15) 0.0590(4) Uani 1 1 d . . .
O1A O 0.5119(2) 0.84493(5) 1.25799(17) 0.0765(5) Uani 1 1 d . . .
N2 N 0.43500(18) 0.42426(5) -0.20054(17) 0.0466(4) Uani 1 1 d . . .
N2A N 0.08401(18) 0.59727(5) 1.25108(16) 0.0456(4) Uani 1 1 d . . .
N1A N 0.11437(19) 0.65156(5) 1.40238(16) 0.0488(4) Uani 1 1 d . . .
N1 N 0.39656(19) 0.37273(5) -0.36329(17) 0.0523(4) Uani 1 1 d . . .
C14 C 0.31787(19) 0.42600(5) 0.05787(18) 0.0367(4) Uani 1 1 d . . .
C14A C 0.19701(19) 0.59296(5) 0.99245(19) 0.0384(4) Uani 1 1 d . . .
C13 C 0.29656(19) 0.39628(5) -0.04318(18) 0.0365(4) Uani 1 1 d . . .
C16A C 0.1962(2) 0.55651(5) 1.0302(2) 0.0435(5) Uani 1 1 d . . .
H16A H 0.2115 0.5507 1.1211 0.052 Uiso 1 1 calc R . .
C12 C 0.35708(19) 0.39696(5) -0.16168(19) 0.0382(4) Uani 1 1 d . . .
C13A C 0.2213(2) 0.62326(5) 1.09017(19) 0.0400(4) Uani 1 1 d . . .
C15 C 0.2131(2) 0.43388(5) 0.13152(19) 0.0431(5) Uani 1 1 d . . .
H15 H 0.1276 0.4209 0.1137 0.052 Uiso 1 1 calc R . .
C18A C 0.1734(2) 0.52865(5) 0.9364(2) 0.0446(5) Uani 1 1 d . . .
H18A H 0.1734 0.5044 0.9641 0.053 Uiso 1 1 calc R . .
C10A C 0.1783(2) 0.65497(5) 1.29600(18) 0.0401(4) Uani 1 1 d . . .
C11 C 0.2166(2) 0.36592(5) -0.03007(19) 0.0433(5) Uani 1 1 d . . .
H11 H 0.1749 0.3644 0.0453 0.052 Uiso 1 1 calc R . .
C12A C 0.16154(19) 0.62389(5) 1.20898(19) 0.0383(4) Uani 1 1 d . . .
C2 C 0.1094(2) 0.20473(5) -0.2701(2) 0.0439(5) Uani 1 1 d . . .
C19 C 0.3568(2) 0.48052(5) 0.25579(19) 0.0418(5) Uani 1 1 d . . .
C15A C 0.1748(2) 0.60063(5) 0.8556(2) 0.0445(5) Uani 1 1 d . . .
H15A H 0.175 0.6248 0.8273 0.053 Uiso 1 1 calc R . .
C8 C 0.2515(2) 0.33684(5) -0.23502(19) 0.0447(5) Uani 1 1 d . . .
C10 C 0.3353(2) 0.36758(5) -0.25644(19) 0.0404(5) Uani 1 1 d . . .
C16 C 0.4421(2) 0.44714(6) 0.0854(2) 0.0465(5) Uani 1 1 d . . .
H16 H 0.5139 0.443 0.037 0.056 Uiso 1 1 calc R . .
C19A C 0.1507(2) 0.53712(5) 0.8015(2) 0.0413(5) Uani 1 1 d . . .
C8A C 0.2563(2) 0.68601(6) 1.26625(19) 0.0454(5) Uani 1 1 d . . .
C7A C 0.3260(2) 0.74693(6) 1.32186(19) 0.0448(5) Uani 1 1 d . . .
C9 C 0.1932(2) 0.33676(6) -0.1234(2) 0.0479(5) Uani 1 1 d . . .
H9 H 0.1366 0.3171 -0.1079 0.057 Uiso 1 1 calc R . .
C7 C 0.1883(2) 0.27564(5) -0.30542(19) 0.0468(5) Uani 1 1 d . . .
C17 C 0.2320(2) 0.46042(6) 0.2304(2) 0.0457(5) Uani 1 1 d . . .
H17 H 0.1609 0.4647 0.2796 0.055 Uiso 1 1 calc R . .
C17A C 0.1525(2) 0.57314(5) 0.7619(2) 0.0461(5) Uani 1 1 d . . .
H17A H 0.1386 0.5788 0.6709 0.055 Uiso 1 1 calc R . .
C9A C 0.3155(2) 0.68459(6) 1.1557(2) 0.0522(5) Uani 1 1 d . . .
H9A H 0.3687 0.7044 1.1353 0.063 Uiso 1 1 calc R . .
C2A C 0.4443(2) 0.81268(6) 1.2727(2) 0.0485(5) Uani 1 1 d . . .
C11A C 0.2981(2) 0.65366(6) 1.0705(2) 0.0503(5) Uani 1 1 d . . .
H11A H 0.3418 0.654 0.9962 0.06 Uiso 1 1 calc R . .
C3A C 0.3156(2) 0.80225(6) 1.1965(2) 0.0530(5) Uani 1 1 d . . .
H3A H 0.2687 0.8172 1.1277 0.064 Uiso 1 1 calc R . .
C18 C 0.4608(2) 0.47380(6) 0.1818(2) 0.0504(5) Uani 1 1 d . . .
H18 H 0.5445 0.4875 0.1976 0.061 Uiso 1 1 calc R . .
C3 C 0.2241(3) 0.21971(6) -0.1840(2) 0.0568(6) Uani 1 1 d . . .
H3 H 0.2744 0.2061 -0.1129 0.068 Uiso 1 1 calc R . .
C6 C 0.0735(2) 0.26125(6) -0.3910(2) 0.0555(6) Uani 1 1 d . . .
H6 H 0.0218 0.2753 -0.4602 0.067 Uiso 1 1 calc R . .
C6A C 0.4539(2) 0.75714(6) 1.3974(2) 0.0567(6) Uani 1 1 d . . .
H6A H 0.5011 0.7419 1.465 0.068 Uiso 1 1 calc R . .
C5A C 0.2562(2) 0.76927(7) 1.2230(2) 0.0590(6) Uani 1 1 d . . .
H5A H 0.1678 0.7623 1.173 0.071 Uiso 1 1 calc R . .
C4 C 0.0355(2) 0.22565(6) -0.3736(2) 0.0586(6) Uani 1 1 d . . .
H4 H -0.0414 0.2155 -0.4327 0.07 Uiso 1 1 calc R . .
C1 C 0.1378(3) 0.14744(6) -0.1569(2) 0.0655(7) Uani 1 1 d . . .
H1A H 0.0944 0.1237 -0.1613 0.098 Uiso 1 1 calc R . .
H1B H 0.1351 0.1584 -0.0715 0.098 Uiso 1 1 calc R . .
H1C H 0.2353 0.1452 -0.1674 0.098 Uiso 1 1 calc R . .
C5 C 0.2640(3) 0.25530(6) -0.2041(2) 0.0641(7) Uani 1 1 d . . .
H5 H 0.3434 0.2654 -0.1479 0.077 Uiso 1 1 calc R . .
C20 C 0.2946(3) 0.51203(7) 0.4435(2) 0.0665(7) Uani 1 1 d . . .
H20A H 0.327 0.5321 0.5025 0.1 Uiso 1 1 calc R . .
H20B H 0.2965 0.49 0.4951 0.1 Uiso 1 1 calc R . .
H20C H 0.1986 0.5167 0.3966 0.1 Uiso 1 1 calc R . .
C4A C 0.5130(3) 0.79012(7) 1.3732(2) 0.0652(7) Uani 1 1 d . . .
H4A H 0.6001 0.7972 1.4253 0.078 Uiso 1 1 calc R . .
C20A C 0.1190(3) 0.47497(6) 0.7342(3) 0.0730(7) Uani 1 1 d . . .
H20D H 0.1001 0.4604 0.654 0.11 Uiso 1 1 calc R . .
H20E H 0.0441 0.4714 0.7839 0.11 Uiso 1 1 calc R . .
H20F H 0.2088 0.4678 0.7885 0.11 Uiso 1 1 calc R . .
C1A C 0.4512(3) 0.86861(7) 1.1536(3) 0.0729(7) Uani 1 1 d . . .
H1A1 H 0.5105 0.8899 1.1553 0.109 Uiso 1 1 calc R . .
H1A2 H 0.3576 0.8758 1.1652 0.109 Uiso 1 1 calc R . .
H1A3 H 0.4441 0.8563 1.0689 0.109 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1A S1A N2A 101.59(9) . .
N2 S1 N1 101.25(9) . .
C8A O2A C7A 117.31(15) . .
C8 O2 C7 118.88(15) . .
C19 O3 C20 118.19(17) . .
C19A O3A C20A 117.57(17) . .
C2 O1 C1 117.52(17) . .
C2A O1A C1A 118.84(19) . .
C12 N2 S1 106.81(13) . .
C12A N2A S1A 106.39(14) . .
C10A N1A S1A 105.41(14) . .
C10 N1 S1 105.72(14) . .
C15 C14 C16 116.64(17) . .
C15 C14 C13 120.58(17) . .
C16 C14 C13 122.78(17) . .
C16A C14A C15A 117.47(18) . .
C16A C14A C13A 123.05(17) . .
C15A C14A C13A 119.48(17) . .
C11 C13 C12 114.80(17) . .
C11 C13 C14 122.16(17) . .
C12 C13 C14 123.04(16) . .
C18A C16A C14A 121.82(18) . .
N2 C12 C10 112.08(17) . .
N2 C12 C13 126.42(17) . .
C10 C12 C13 121.47(17) . .
C11A C13A C12A 115.02(18) . .
C11A C13A C14A 122.11(18) . .
C12A C13A C14A 122.82(17) . .
C17 C15 C14 122.02(18) . .
C19A C18A C16A 119.38(18) . .
N1A C10A C8A 125.61(18) . .
N1A C10A C12A 114.09(17) . .
C8A C10A C12A 120.31(17) . .
C13 C11 C9 124.41(18) . .
N2A C12A C10A 112.52(17) . .
N2A C12A C13A 126.27(18) . .
C10A C12A C13A 121.20(17) . .
O1 C2 C3 124.26(19) . .
O1 C2 C4 116.53(18) . .
C3 C2 C4 119.2(2) . .
O3 C19 C18 115.96(18) . .
O3 C19 C17 124.71(18) . .
C18 C19 C17 119.32(18) . .
C17A C15A C14A 121.11(18) . .
C9 C8 O2 126.89(19) . .
C9 C8 C10 117.67(18) . .
O2 C8 C10 115.40(18) . .
N1 C10 C8 125.56(18) . .
N1 C10 C12 114.14(17) . .
C8 C10 C12 120.28(18) . .
C18 C16 C14 121.65(18) . .
O3A C19A C18A 125.00(18) . .
O3A C19A C17A 115.26(18) . .
C18A C19A C17A 119.74(18) . .
C9A C8A O2A 126.80(19) . .
C9A C8A C10A 117.77(18) . .
O2A C8A C10A 115.43(17) . .
C6A C7A C5A 120.3(2) . .
C6A C7A O2A 118.21(19) . .
C5A C7A O2A 121.29(19) . .
C8 C9 C11 121.36(19) . .
C5 C7 C6 120.8(2) . .
C5 C7 O2 121.01(19) . .
C6 C7 O2 117.81(18) . .
C19 C17 C15 119.69(18) . .
C15A C17A C19A 120.48(19) . .
C8A C9A C11A 121.35(19) . .
O1A C2A C3A 124.6(2) . .
O1A C2A C4A 115.67(19) . .
C3A C2A C4A 119.7(2) . .
C13A C11A C9A 124.31(19) . .
C2A C3A C5A 119.3(2) . .
C16 C18 C19 120.64(19) . .
C2 C3 C5 119.4(2) . .
C7 C6 C4 118.9(2) . .
C7A C6A C4A 119.7(2) . .
C7A C5A C3A 120.5(2) . .
C6 C4 C2 121.2(2) . .
C7 C5 C3 120.5(2) . .
C6A C4A C2A 120.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1A N1A 1.6072(18) .
S1A N2A 1.6097(17) .
S1 N2 1.6042(17) .
S1 N1 1.6118(18) .
O2A C8A 1.365(2) .
O2A C7A 1.401(2) .
O2 C8 1.371(2) .
O2 C7 1.406(2) .
O3 C19 1.374(2) .
O3 C20 1.420(3) .
O3A C19A 1.368(2) .
O3A C20A 1.411(3) .
O1 C2 1.370(2) .
O1 C1 1.413(3) .
O1A C2A 1.366(3) .
O1A C1A 1.402(3) .
N2 C12 1.349(2) .
N2A C12A 1.342(2) .
N1A C10A 1.345(2) .
N1 C10 1.341(3) .
C14 C15 1.390(3) .
C14 C16 1.396(3) .
C14 C13 1.481(3) .
C14A C16A 1.388(3) .
C14A C15A 1.391(3) .
C14A C13A 1.475(3) .
C13 C11 1.368(3) .
C13 C12 1.432(3) .
C16A C18A 1.383(3) .
C12 C10 1.430(3) .
C13A C11A 1.367(3) .
C13A C12A 1.431(3) .
C15 C17 1.383(3) .
C18A C19A 1.378(3) .
C10A C8A 1.422(3) .
C10A C12A 1.430(3) .
C11 C9 1.415(3) .
C2 C3 1.373(3) .
C2 C4 1.377(3) .
C19 C18 1.378(3) .
C19 C17 1.379(3) .
C15A C17A 1.372(3) .
C8 C9 1.356(3) .
C8 C10 1.421(3) .
C16 C18 1.368(3) .
C19A C17A 1.379(3) .
C8A C9A 1.352(3) .
C7A C6A 1.359(3) .
C7A C5A 1.362(3) .
C7 C5 1.357(3) .
C7 C6 1.363(3) .
C9A C11A 1.414(3) .
C2A C3A 1.370(3) .
C2A C4A 1.375(3) .
C3A C5A 1.382(3) .
C3 C5 1.383(3) .
C6 C4 1.373(3) .
C6A C4A 1.374(3) .
