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#$Date: 2023-12-14 11:11:42 +0200 (Thu, 14 Dec 2023) $
#$Revision: 288302 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/77/8107720.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_8107720
loop_
_publ_author_name
'Schmitt, Bonell'
'Gerber, Thomas I. A.'
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 Crystal structure of (6E)-2-[(ortho-hydroxy)benzylidene]-1-[4,5-dihydro-
 5-(ortho-hydroxy-phenyl)-1,3,4-thiadiazo-2-yl-4-isoproylidenonium]-
 hydrazine chloride, C18H19ClN4O2S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              69
_journal_page_last               70
_journal_paper_doi               10.1515/ncrs-2014-0229
_journal_volume                  230
_journal_year                    2015
_chemical_formula_sum            'C18 H19 Cl N4 O2 S'
_chemical_formula_weight         390.886
_chemical_name_common
;
(6E)-2-[(ortho-hydroxy)benzylidene]-1-[4,5-dihydro-
5-(ortho-hydroxy-phenyl)-1,3,4-thiadiazo-2-yl-4-isoproylidenonium]-
hydrazine chloride
;
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_cell_angle_alpha                90.
_cell_angle_beta                 101.986(9)
_cell_angle_gamma                90.
_cell_formula_units_Z            8
_cell_length_a                   15.771(4)
_cell_length_b                   11.101(3)
_cell_length_c                   22.072(6)
_cell_volume                     3780.0(17)
_diffrn_ambient_temperature      200
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    0.333
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1632
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3498
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_gt          0.1538
_cod_data_source_file            Z-2015-069.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               8107720
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,y,-z
3 -x,-y,-z
4 1/2+x,-y,z
5 1/2+x,1/2+y,1/2+z
6 -x,1/2+y,1/2-z
7 1/2-x,1/2-y,1/2-z
8 x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S Uani 0.33382(5) 0.20843(6) 0.12487(3) 1.000 0.0461(2) . . . .
Cl1 Cl Uani 0.10610(5) 0.40893(6) 0.09990(3) 1.000 0.0463(2) . . . .
O1 O Uani 0.3922(2) -0.0968(2) 0.04420(10) 1.000 0.0646(8) . . . .
O2 O Uani 0.36260(10) 0.2223(2) 0.28065(8) 1.000 0.0472(6) . . . .
N1 N Uani 0.36620(10) 0.1322(2) 0.00560(10) 1.000 0.0453(6) . . . .
N2 N Uani 0.35600(10) 0.2547(2) 0.01020(10) 1.000 0.0431(6) . . . .
N3 N Uani 0.33700(10) 0.4181(2) 0.06901(9) 1.000 0.0405(6) . . . .
N4 N Uani 0.32060(10) 0.4447(2) 0.12704(8) 1.000 0.0379(6) . . . .
C1 C Uani 0.3800(2) 0.0949(3) -0.04770(10) 1.000 0.0452(8) . . . .
C2 C Uani 0.3437(2) 0.3017(2) 0.06340(10) 1.000 0.0382(6) . . . .
C3 C Uani 0.3350(2) 0.3448(2) 0.17300(10) 1.000 0.0390(6) . . . .
C4 C Uani 0.2959(2) 0.5515(3) 0.13850(10) 1.000 0.0423(8) . . . .
C5 C Uani 0.2798(2) 0.5847(3) 0.20040(10) 1.000 0.0541(10) . . . .
C6 C Uani 0.2840(2) 0.6441(3) 0.08900(10) 1.000 0.0523(10) . . . .
C11 C Uani 0.3952(2) -0.0302(3) -0.05910(10) 1.000 0.0447(8) . . . .
C12 C Uani 0.4027(2) -0.1208(3) -0.01380(10) 1.000 0.0478(8) . . . .
C13 C Uani 0.4238(2) -0.2380(3) -0.0274(2) 1.000 0.0572(12) . . . .
C14 C Uani 0.4352(2) -0.2668(3) -0.0866(2) 1.000 0.0606(12) . . . .
C15 C Uani 0.4262(2) -0.1812(3) -0.1320(2) 1.000 0.0576(12) . . . .
C16 C Uani 0.4077(2) -0.0633(3) -0.11820(10) 1.000 0.0542(10) . . . .
C21 C Uani 0.4195(2) 0.3595(2) 0.21850(10) 1.000 0.0352(6) . . . .
C22 C Uani 0.4306(2) 0.2921(2) 0.27330(10) 1.000 0.0365(6) . . . .
C23 C Uani 0.5074(2) 0.3016(2) 0.31720(10) 1.000 0.0432(8) . . . .
C24 C Uani 0.5722(2) 0.3770(3) 0.30670(10) 1.000 0.0460(8) . . . .
C25 C Uani 0.5619(2) 0.4439(3) 0.25290(10) 1.000 0.0467(8) . . . .
C26 C Uani 0.4859(2) 0.4345(2) 0.20900(10) 1.000 0.0433(8) . . . .
H1 H Uiso 0.38000 0.15190 -0.07980 1.000 0.0540 . . . .
H2 H Uiso 0.37560 0.18520 0.31450 1.000 0.0710 . . . .
H3 H Uiso 0.28610 0.34170 0.19550 1.000 0.0470 . . . .
H5A H Uiso 0.22000 0.61280 0.19600 1.000 0.0810 . . . .
H5B H Uiso 0.31980 0.64900 0.21830 1.000 0.0810 . . . .
H5C H Uiso 0.28920 0.51410 0.22760 1.000 0.0810 . . . .
H6A H Uiso 0.33830 0.65450 0.07470 1.000 0.0790 . . . .
H6B H Uiso 0.26740 0.72070 0.10530 1.000 0.0790 . . . .
H6C H Uiso 0.23820 0.61820 0.05430 1.000 0.0790 . . . .
H13 H Uiso 0.43060 -0.29840 0.00370 1.000 0.0690 . . . .
H14 H Uiso 0.44930 -0.34720 -0.09550 1.000 0.0720 . . . .
H15 H Uiso 0.43260 -0.20210 -0.17260 1.000 0.0690 . . . .
H16 H Uiso 0.40340 -0.00340 -0.14940 1.000 0.0650 . . . .
H23 H Uiso 0.51510 0.25620 0.35440 1.000 0.0520 . . . .
H24 H Uiso 0.62470 0.38310 0.33680 1.000 0.0550 . . . .
H25 H Uiso 0.60690 0.49590 0.24610 1.000 0.0560 . . . .
H26 H Uiso 0.47890 0.48000 0.17190 1.000 0.0520 . . . .
H72 H Uiso 0.362(3) 0.311(4) -0.019(2) 1.000 0.090(10) . . . .
H81 H Uiso 0.36590 -0.03110 0.04440 1.000 0.0970 . . . .
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 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 ' 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 0.0060 ' 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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C3 88.22(11) . . . yes
N2 N1 C1 115.1(2) . . . yes
C12 O1 H81 110.00 . . . no
N1 N2 C2 119.5(2) . . . yes
C22 O2 H2 109.00 . . . no
N4 N3 C2 109.4(2) . . . yes
N3 N4 C4 119.9(2) . . . yes
N3 N4 C3 116.01(19) . . . yes
C3 N4 C4 124.13(19) . . . yes
N1 C1 C11 121.8(2) . . . yes
N2 C2 N3 120.0(2) . . . yes
C2 N2 H72 114(3) . . . no
S1 C2 N3 119.57(18) . . . yes
S1 C2 N2 120.42(18) . . . yes
N1 N2 H72 126(3) . . . no
S1 C3 C21 112.04(19) . . . yes
N4 C3 C21 111.3(2) . . . yes
S1 C3 N4 103.70(14) . . . yes
N4 C4 C5 121.6(2) . . . yes
N4 C4 C6 119.3(2) . . . yes
C5 C4 C6 119.0(3) . . . no
C1 C11 C12 123.9(2) . . . no
C12 C11 C16 117.7(3) . . . no
C1 C11 C16 118.3(3) . . . no
O1 C12 C11 121.6(3) . . . yes
O1 C12 C13 118.1(3) . . . yes
C11 C12 C13 120.3(3) . . . no
C12 C13 C14 120.0(3) . . . no
C13 C14 C15 121.0(3) . . . no
C14 C15 C16 119.3(4) . . . no
C11 C16 C15 121.7(3) . . . no
C3 C21 C26 123.9(2) . . . no
C22 C21 C26 119.2(2) . . . no
C3 C21 C22 117.0(2) . . . no
O2 C22 C21 116.5(2) . . . yes
O2 C22 C23 123.7(2) . . . yes
C21 C22 C23 119.7(3) . . . no
C22 C23 C24 119.9(2) . . . no
C23 C24 C25 120.8(3) . . . no
C24 C25 C26 119.5(3) . . . no
C21 C26 C25 120.8(2) . . . no
N1 C1 H1 119.00 . . . no
C11 C1 H1 119.00 . . . no
S1 C3 H3 110.00 . . . no
N4 C3 H3 110.00 . . . no
C21 C3 H3 110.00 . . . no
C4 C5 H5A 109.00 . . . no
C4 C5 H5B 109.00 . . . no
C4 C5 H5C 109.00 . . . no
H5A C5 H5B 110.00 . . . no
H5A C5 H5C 110.00 . . . no
H5B C5 H5C 109.00 . . . no
C4 C6 H6A 110.00 . . . no
C4 C6 H6B 109.00 . . . no
C4 C6 H6C 109.00 . . . no
H6A C6 H6B 110.00 . . . no
H6A C6 H6C 110.00 . . . no
H6B C6 H6C 109.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C13 C14 H14 119.00 . . . no
C15 C14 H14 120.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C15 H15 120.00 . . . no
C11 C16 H16 119.00 . . . no
C15 C16 H16 119.00 . . . no
C22 C23 H23 120.00 . . . no
C24 C23 H23 120.00 . . . no
C23 C24 H24 120.00 . . . no
C25 C24 H24 120.00 . . . no
C24 C25 H25 120.00 . . . no
C26 C25 H25 120.00 . . . no
C21 C26 H26 120.00 . . . no
C25 C26 H26 120.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.739(2) . . yes
S1 C3 1.847(2) . . yes
O1 C12 1.351(3) . . yes
O2 C22 1.360(3) . . yes
N1 N2 1.376(3) . . yes
N1 C1 1.307(3) . . yes
O1 H81 0.8400 . . no
O2 H2 0.8400 . . no
N2 C2 1.335(3) . . yes
N3 C2 1.305(3) . . yes
N3 N4 1.390(3) . . yes
N4 C3 1.488(3) . . yes
N4 C4 1.289(4) . . yes
C1 C11 1.440(5) . . no
N2 H72 0.92(4) . . no
C3 C21 1.502(4) . . no
C4 C6 1.483(4) . . no
C4 C5 1.487(3) . . no
C11 C16 1.408(3) . . no
C11 C12 1.406(4) . . no
C12 C13 1.391(5) . . no
C13 C14 1.393(6) . . no
C14 C15 1.367(5) . . no
C15 C16 1.389(5) . . no
C21 C26 1.387(4) . . no
C21 C22 1.402(3) . . no
C22 C23 1.389(4) . . no
C23 C24 1.377(4) . . no
C24 C25 1.381(4) . . no
C25 C26 1.380(4) . . no
C1 H1 0.9500 . . no
C3 H3 1.0000 . . no
C5 H5A 0.9800 . . no
C5 H5B 0.9800 . . no
C5 H5C 0.9800 . . no
C6 H6A 0.9800 . . no
C6 H6B 0.9800 . . no
C6 H6C 0.9800 . . no
C13 H13 0.9500 . . no
C14 H14 0.9500 . . no
C15 H15 0.9500 . . no
C16 H16 0.9500 . . no
C23 H23 0.9500 . . no
C24 H24 0.9500 . . no
C25 H25 0.9500 . . no
C26 H26 0.9500 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 Cl1 0.8400 2.1300 2.963(2) 174.00 7_555 yes
N2 H72 Cl1 0.92(4) 2.24(4) 3.130(2) 165(4) 2_555 yes
O1 H81 N1 0.8400 2.0100 2.685(3) 138.00 . yes
C26 H26 N4 0.9500 2.5200 2.850(3) 101.00 . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 S1 C2 N2 173.1(3) . . . . no
C3 S1 C2 N3 -8.5(2) . . . . no
C2 S1 C3 N4 13.99(19) . . . . no
C2 S1 C3 C21 -106.2(2) . . . . no
C1 N1 N2 C2 -178.4(2) . . . . no
N2 N1 C1 C11 177.7(2) . . . . no
N1 N2 C2 S1 -4.0(3) . . . . no
N1 N2 C2 N3 177.6(2) . . . . no
C2 N3 N4 C3 13.9(3) . . . . no
C2 N3 N4 C4 -167.3(2) . . . . no
N4 N3 C2 S1 -1.1(3) . . . . no
N4 N3 C2 N2 177.3(2) . . . . no
N3 N4 C3 S1 -18.9(2) . . . . no
N3 N4 C3 C21 101.8(2) . . . . no
C4 N4 C3 S1 162.3(2) . . . . no
C4 N4 C3 C21 -77.1(3) . . . . no
N3 N4 C4 C5 -178.4(2) . . . . no
N3 N4 C4 C6 1.0(4) . . . . no
C3 N4 C4 C5 0.4(4) . . . . no
C3 N4 C4 C6 179.8(2) . . . . no
N1 C1 C11 C12 -4.7(5) . . . . no
N1 C1 C11 C16 178.7(3) . . . . no
S1 C3 C21 C22 -81.2(3) . . . . no
S1 C3 C21 C26 98.5(2) . . . . no
N4 C3 C21 C22 163.2(2) . . . . no
N4 C3 C21 C26 -17.1(3) . . . . no
C1 C11 C12 O1 3.0(5) . . . . no
C1 C11 C12 C13 -175.2(3) . . . . no
C16 C11 C12 O1 179.6(3) . . . . no
C16 C11 C12 C13 1.5(5) . . . . no
C1 C11 C16 C15 177.3(3) . . . . no
C12 C11 C16 C15 0.5(5) . . . . no
O1 C12 C13 C14 180.0(3) . . . . no
C11 C12 C13 C14 -1.8(5) . . . . no
C12 C13 C14 C15 0.2(5) . . . . no
C13 C14 C15 C16 1.7(5) . . . . no
C14 C15 C16 C11 -2.1(5) . . . . no
C3 C21 C22 O2 -1.8(3) . . . . no
C3 C21 C22 C23 179.9(2) . . . . no
C26 C21 C22 O2 178.6(2) . . . . no
C26 C21 C22 C23 0.2(4) . . . . no
C3 C21 C26 C25 179.9(3) . . . . no
C22 C21 C26 C25 -0.5(4) . . . . no
O2 C22 C23 C24 -178.3(3) . . . . no
C21 C22 C23 C24 0.0(4) . . . . no
C22 C23 C24 C25 0.1(4) . . . . no
C23 C24 C25 C26 -0.4(5) . . . . no
C24 C25 C26 C21 0.6(4) . . . . no
