#------------------------------------------------------------------------------
#$Date: 2022-09-14 23:33:16 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/09/4020913.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_4020913
loop_
_publ_author_name
'Md. Akhtaruzzaman'
'Masaaki Tomura'
'Jun-ichi Nishida'
'Yoshiro Yamashita'
_publ_section_title
;
 Synthesis and Characterization of Novel Dipyridylbenzothiadiazole
 and Bisbenzothiadiazole Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2953
_journal_page_last               2958
_journal_paper_doi               10.1021/jo035800h
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         'C18 H16 N4 S, 2(C F3 O3 S), O'
_chemical_formula_sum            'C20 H16 F6 N4 O7 S3'
_chemical_formula_weight         634.55
_chemical_melting_point          419.0(10)
_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'
_cell_angle_alpha                67.544(17)
_cell_angle_beta                 77.59(2)
_cell_angle_gamma                67.938(18)
_cell_formula_units_Z            2
_cell_length_a                   8.7475(13)
_cell_length_b                   11.3927(15)
_cell_length_c                   14.991(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1275.2(3)
_diffrn_ambient_temperature      296(2)
_exptl_crystal_density_diffrn    1.653
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '418-420' was changed to '419.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4020913
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.67318(16) -0.22442(13) 0.88076(12) 0.0716(8) Uani 1 1 d . . .
S2 S 0.19222(18) -0.36355(16) 0.86764(11) 0.0763(8) Uani 1 1 d . . .
S3 S -0.1834(2) -0.29195(18) 0.50949(12) 0.0810(8) Uani 1 1 d D . .
F1 F 0.3540(8) -0.2704(6) 0.7046(4) 0.161(2) Uani 1 1 d . . .
F2 F 0.1063(9) -0.1511(7) 0.7155(4) 0.167(3) Uani 1 1 d . . .
F3 F 0.2772(6) -0.1471(5) 0.7927(4) 0.1239(17) Uani 1 1 d . . .
F4 F -0.302(3) -0.052(2) 0.478(2) 0.27(2) Uani 0.451(17) 1 d PD A 1
F5 F -0.357(3) -0.151(4) 0.618(2) 0.31(3) Uani 0.451(17) 1 d PD A 1
F6 F -0.134(3) -0.125(3) 0.575(2) 0.219(17) Uani 0.451(17) 1 d PD A 1
F7 F -0.148(2) -0.188(3) 0.6186(19) 0.234(13) Uani 0.549(17) 1 d PD A 2
F8 F -0.213(4) -0.0520(19) 0.4815(18) 0.36(3) Uani 0.549(17) 1 d PD A 2
F9 F -0.3903(15) -0.116(2) 0.5853(16) 0.173(8) Uani 0.549(17) 1 d PD A 2
O1 O 0.1464(7) -0.4364(6) 0.8279(5) 0.126(2) Uani 1 1 d . . .
O2 O 0.3505(7) -0.4336(6) 0.9044(5) 0.139(2) Uani 1 1 d . . .
O3 O 0.0725(7) -0.2948(5) 0.9267(4) 0.1113(18) Uani 1 1 d . . .
O4 O -0.0468(17) -0.286(3) 0.4451(10) 0.093(6) Uani 0.451(17) 1 d PD A 1
O5 O -0.314(2) -0.2997(17) 0.4760(13) 0.129(7) Uani 0.451(17) 1 d PD A 1
O6 O -0.1399(19) -0.4002(12) 0.5994(8) 0.112(6) Uani 0.451(17) 1 d PD A 1
O7 O -0.292(2) -0.217(3) 0.4355(15) 0.34(2) Uani 0.549(17) 1 d PD A 2
O8 O -0.226(3) -0.3899(17) 0.5831(15) 0.30(2) Uani 0.549(17) 1 d PD A 2
O9 O -0.0184(15) -0.313(2) 0.4761(13) 0.102(5) Uani 0.549(17) 1 d PD A 2
O10 O 0.1649(10) -0.5069(9) 0.6529(7) 0.172(3) Uani 1 1 d . . .
N1 N 0.6393(5) -0.0670(4) 0.8172(3) 0.0591(12) Uani 1 1 d . . .
N2 N 0.5173(5) -0.2161(4) 0.9594(3) 0.0567(11) Uani 1 1 d . . .
N3 N 0.6389(5) 0.2798(4) 0.5898(3) 0.0590(12) Uani 1 1 d . . .
N4 N 0.1549(5) -0.3268(4) 1.1582(3) 0.0603(12) Uani 1 1 d . . .
C1 C 0.4243(5) 0.1439(4) 0.8288(3) 0.0464(11) Uani 1 1 d . . .
C2 C 0.4978(5) -0.0005(4) 0.8584(3) 0.0468(11) Uani 1 1 d . . .
C3 C 0.4270(5) -0.0855(4) 0.9394(3) 0.0467(11) Uani 1 1 d . . .
C4 C 0.2799(5) -0.0312(4) 0.9929(3) 0.0447(11) Uani 1 1 d . . .
C5 C 0.2125(5) 0.1072(4) 0.9626(3) 0.0487(11) Uani 1 1 d . . .
H5 H 0.1151 0.1464 0.9952 0.058 Uiso 1 1 calc R . .
C6 C 0.2853(5) 0.1906(4) 0.8848(3) 0.0500(11) Uani 1 1 d . . .
H6 H 0.2365 0.2830 0.8701 0.060 Uiso 1 1 calc R . .
C7 C 0.4990(5) 0.2329(4) 0.7465(3) 0.0469(11) Uani 1 1 d . . .
C8 C 0.5699(6) 0.1990(5) 0.6649(3) 0.0563(13) Uani 1 1 d . . .
H8 H 0.5702 0.1191 0.6614 0.068 Uiso 1 1 calc R . .
C9 C 0.6432(6) 0.3957(5) 0.5917(4) 0.0612(13) Uani 1 1 d . . .
H9 H 0.6944 0.4486 0.5397 0.073 Uiso 1 1 calc R . .
C10 C 0.5720(6) 0.4348(5) 0.6703(4) 0.0634(14) Uani 1 1 d . . .
H10 H 0.5734 0.5153 0.6718 0.076 Uiso 1 1 calc R . .
C11 C 0.4981(5) 0.3559(5) 0.7476(4) 0.0554(12) Uani 1 1 d . . .
H11 H 0.4475 0.3839 0.8006 0.067 Uiso 1 1 calc R . .
C12 C 0.2005(5) -0.1175(4) 1.0760(3) 0.0477(11) Uani 1 1 d . . .
C13 C 0.2242(5) -0.2477(5) 1.0821(3) 0.0521(12) Uani 1 1 d . . .
H13 H 0.2883 -0.2805 1.0332 0.063 Uiso 1 1 calc R . .
C14 C 0.0615(6) -0.2841(5) 1.2297(4) 0.0634(14) Uani 1 1 d . . .
H14 H 0.0148 -0.3413 1.2811 0.076 Uiso 1 1 calc R . .
C15 C 0.0335(6) -0.1566(5) 1.2280(4) 0.0633(14) Uani 1 1 d . . .
H15 H -0.0313 -0.1270 1.2780 0.076 Uiso 1 1 calc R . .
C16 C 0.1034(6) -0.0723(5) 1.1505(4) 0.0583(13) Uani 1 1 d . . .
H16 H 0.0852 0.0145 1.1484 0.070 Uiso 1 1 calc R . .
C17 C 0.7132(9) 0.2362(8) 0.5042(4) 0.0880(19) Uani 1 1 d . . .
H17A H 0.7961 0.1494 0.5239 0.132 Uiso 1 1 calc R . .
H17B H 0.7631 0.2998 0.4576 0.132 Uiso 1 1 calc R . .
H17C H 0.6286 0.2314 0.4755 0.132 Uiso 1 1 calc R . .
C18 C 0.1889(9) -0.4676(6) 1.1604(5) 0.0827(18) Uani 1 1 d . . .
H18A H 0.2818 -0.5275 1.1974 0.124 Uiso 1 1 calc R . .
H18B H 0.2133 -0.4701 1.0954 0.124 Uiso 1 1 calc R . .
H18C H 0.0933 -0.4948 1.1897 0.124 Uiso 1 1 calc R . .
C19 C 0.2354(10) -0.2244(8) 0.7655(5) 0.096(2) Uani 1 1 d . . .
C20 C -0.2398(10) -0.1520(10) 0.5519(7) 0.121(3) Uani 1 1 d D A .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N2 1.599(4) . ?
S1 N1 1.621(4) . ?
S2 O1 1.391(5) . ?
S2 O3 1.417(5) . ?
S2 O2 1.421(5) . ?
S2 C19 1.830(9) . ?
S3 O8 1.338(12) . ?
S3 O4 1.371(11) . ?
S3 O9 1.384(11) . ?
S3 O5 1.389(10) . ?
S3 O7 1.406(13) . ?
S3 O6 1.442(7) . ?
S3 C20 1.799(10) . ?
F1 C19 1.317(8) . ?
F2 C19 1.308(9) . ?
F3 C19 1.288(8) . ?
F4 C20 1.286(14) . ?
F5 C20 1.265(15) . ?
F6 C20 1.230(14) . ?
F7 C20 1.267(14) . ?
F8 C20 1.283(14) . ?
F9 C20 1.272(12) . ?
N1 C2 1.347(6) . ?
N2 C3 1.343(5) . ?
N3 C9 1.347(7) . ?
N3 C8 1.347(6) . ?
N3 C17 1.484(7) . ?
N4 C14 1.332(7) . ?
N4 C13 1.345(6) . ?
N4 C18 1.506(7) . ?
C1 C6 1.372(6) . ?
C1 C2 1.445(6) . ?
C1 C7 1.474(6) . ?
C2 C3 1.422(6) . ?
C3 C4 1.421(6) . ?
C4 C5 1.382(6) . ?
C4 C12 1.485(6) . ?
C5 C6 1.399(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.374(6) . ?
C7 C11 1.405(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.362(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(7) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.389(6) . ?
C12 C16 1.391(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
