#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/09/4020915.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_4020915
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         'C16 H12 N4 S, C6 Cl2 O4, 3(H2 O)'
_chemical_formula_sum            'C22 H18 Cl2 N4 O7 S'
_chemical_formula_weight         553.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 113.937(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.386(10)
_cell_length_b                   6.908(3)
_cell_length_c                   20.683(12)
_cell_measurement_temperature    296(2)
_cell_volume                     2270(2)
_diffrn_ambient_temperature      296(2)
_exptl_crystal_density_diffrn    1.619
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4020915
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
Cl1 Cl 0.33898(7) 0.62527(19) 0.12539(6) 0.0582(10) Uani 1 1 d . . .
Cl2 Cl 0.07841(7) 0.8168(2) 0.25871(6) 0.0745(11) Uani 1 1 d . . .
S1 S 0.43264(7) 0.09329(19) 0.22588(6) 0.0519(10) Uani 1 1 d . . .
O1 O 0.37282(17) 0.6828(4) 0.27731(14) 0.0519(12) Uani 1 1 d . . .
O2 O 0.26524(17) 0.7754(5) 0.33368(14) 0.0519(12) Uani 1 1 d . . .
O3 O 0.04531(17) 0.7670(5) 0.10636(14) 0.0557(13) Uani 1 1 d . . .
O4 O 0.15556(17) 0.7118(5) 0.04968(13) 0.0502(12) Uani 1 1 d . . .
O5 O 0.7549(3) 0.4757(8) 0.5096(3) 0.116(2) Uani 1 1 d D . .
H5A H 0.779(4) 0.403(8) 0.484(3) 0.139 Uiso 1 1 d D . .
H5B H 0.798(3) 0.552(9) 0.543(3) 0.139 Uiso 1 1 d D . .
O6 O 0.7912(3) 0.0312(6) 0.5663(2) 0.0874(15) Uani 1 1 d D . .
H6A H 0.787(4) 0.116(6) 0.600(2) 0.105 Uiso 1 1 d D . .
H6B H 0.795(4) 0.107(6) 0.530(2) 0.105 Uiso 1 1 d D . .
O7 O 0.1156(2) 0.1991(6) -0.1080(2) 0.0729(14) Uani 1 1 d D . .
H7A H 0.147(2) 0.089(4) -0.109(3) 0.088 Uiso 1 1 d D . .
H7B H 0.0594(11) 0.165(6) -0.121(3) 0.088 Uiso 1 1 d D . .
N1 N 0.4539(2) 0.1389(5) 0.30756(17) 0.0459(13) Uani 1 1 d . . .
N2 N 0.3328(2) 0.1367(5) 0.19030(16) 0.0443(13) Uani 1 1 d . . .
N3 N 0.5680(3) 0.2557(5) 0.5770(2) 0.0567(14) Uani 1 1 d . . .
H3 H 0.608(3) 0.263(7) 0.616(3) 0.068 Uiso 1 1 d . . .
N4 N 0.0108(2) 0.2542(6) 0.04387(18) 0.0518(13) Uani 1 1 d . . .
H4 H -0.035(3) 0.261(7) 0.005(2) 0.062 Uiso 1 1 d . . .
C1 C 0.3699(2) 0.2448(5) 0.37340(18) 0.0359(13) Uani 1 1 d . . .
C2 C 0.3808(2) 0.1937(5) 0.31069(19) 0.0353(13) Uani 1 1 d . . .
C3 C 0.3108(2) 0.1923(5) 0.24327(18) 0.0352(13) Uani 1 1 d . . .
C4 C 0.2277(2) 0.2445(5) 0.23660(18) 0.0355(13) Uani 1 1 d . . .
C5 C 0.2219(2) 0.2966(6) 0.29839(19) 0.0417(13) Uani 1 1 d . . .
H5 H 0.1696 0.3345 0.2964 0.050 Uiso 1 1 calc R . .
C6 C 0.2908(2) 0.2958(6) 0.36486(19) 0.0413(13) Uani 1 1 d . . .
H6 H 0.2818 0.3317 0.4046 0.050 Uiso 1 1 calc R . .
C7 C 0.4401(2) 0.2461(5) 0.44431(18) 0.0377(13) Uani 1 1 d . . .
C8 C 0.5228(2) 0.2890(6) 0.4549(2) 0.0444(13) Uani 1 1 d . . .
H8 H 0.5354 0.3155 0.4161 0.053 Uiso 1 1 calc R . .
C9 C 0.5852(3) 0.2923(6) 0.5212(2) 0.0530(15) Uani 1 1 d . . .
H9 H 0.6401 0.3205 0.5275 0.064 Uiso 1 1 calc R . .
C10 C 0.4903(3) 0.2136(6) 0.5703(2) 0.0523(15) Uani 1 1 d . . .
H10 H 0.4800 0.1880 0.6102 0.063 Uiso 1 1 calc R . .
C11 C 0.4257(3) 0.2083(6) 0.50464(19) 0.0433(13) Uani 1 1 d . . .
H11 H 0.3715 0.1791 0.5002 0.052 Uiso 1 1 calc R . .
C12 C 0.1528(2) 0.2455(6) 0.16857(19) 0.0378(13) Uani 1 1 d . . .
C13 C 0.1577(3) 0.2407(7) 0.1035(2) 0.0503(14) Uani 1 1 d . . .
H13 H 0.2100 0.2339 0.1013 0.060 Uiso 1 1 calc R . .
C14 C 0.0864(3) 0.2460(7) 0.0425(2) 0.0570(15) Uani 1 1 d . . .
H14 H 0.0908 0.2437 -0.0008 0.068 Uiso 1 1 calc R . .
C15 C 0.0028(3) 0.2586(8) 0.1051(2) 0.0624(16) Uani 1 1 d . . .
H15 H -0.0504 0.2650 0.1055 0.075 Uiso 1 1 calc R . .
C16 C 0.0723(3) 0.2538(8) 0.1672(2) 0.0572(15) Uani 1 1 d . . .
H16 H 0.0658 0.2560 0.2096 0.069 Uiso 1 1 calc R . .
C17 C 0.2672(2) 0.6795(6) 0.16134(19) 0.0417(13) Uani 1 1 d . . .
C18 C 0.2977(2) 0.7016(6) 0.23545(19) 0.0408(13) Uani 1 1 d . . .
C19 C 0.2350(2) 0.7537(6) 0.2677(2) 0.0421(13) Uani 1 1 d . . .
C20 C 0.1504(2) 0.7686(6) 0.2225(2) 0.0450(14) Uani 1 1 d . . .
C21 C 0.1205(2) 0.7514(6) 0.14846(19) 0.0415(13) Uani 1 1 d . . .
C22 C 0.1838(2) 0.7138(6) 0.11571(19) 0.0397(13) Uani 1 1 d . . .
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
Cl1 C17 1.733(4) . ?
Cl2 C20 1.733(4) . ?
S1 N1 1.607(4) . ?
S1 N2 1.615(4) . ?
O1 C18 1.247(4) . ?
O2 C19 1.257(4) . ?
O3 C21 1.248(4) . ?
O4 C22 1.250(4) . ?
O5 H5A 0.944(13) . ?
O5 H5B 0.945(13) . ?
O6 H6A 0.942(13) . ?
O6 H6B 0.939(13) . ?
O7 H7A 0.939(13) . ?
O7 H7B 0.931(13) . ?
N1 C2 1.352(5) . ?
N2 C3 1.355(5) . ?
N3 C9 1.329(6) . ?
N3 C10 1.333(6) . ?
N3 H3 0.82(5) . ?
N4 C14 1.326(6) . ?
N4 C15 1.330(6) . ?
N4 H4 0.88(5) . ?
C1 C6 1.359(5) . ?
C1 C2 1.430(5) . ?
C1 C7 1.480(5) . ?
C2 C3 1.432(5) . ?
C3 C4 1.440(5) . ?
C4 C5 1.370(5) . ?
C4 C12 1.479(5) . ?
C5 C6 1.411(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.394(5) . ?
C7 C8 1.395(5) . ?
C8 C9 1.361(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.367(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.383(5) . ?
C12 C16 1.390(6) . ?
C13 C14 1.365(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.360(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.393(5) . ?
C17 C18 1.412(5) . ?
C18 C19 1.533(6) . ?
C19 C20 1.390(5) . ?
C20 C21 1.408(5) . ?
C21 C22 1.530(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658484
2 PubChem 139089634
