#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224362.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224362
loop_
_publ_author_name
'Goh, Jia Hao'
'Fun, Hoong-Kun'
'Adhikari, Adithya'
'Kalluraya, B.'
_publ_section_title
;(E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1H-1,2,4-triazole-5(4H)-thione
 N,N-dimethylformamide solvate
;
_journal_coeditor_code           LH2959
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3235
_journal_page_last               o3236
_journal_paper_doi               10.1107/S1600536809050090
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H11 N5 O S, C3 H7 N O'
_chemical_formula_moiety         'C13 H11 N5 O S, C3 H7 N O'
_chemical_formula_sum            'C16 H18 N6 O2 S'
_chemical_formula_weight         358.42
_chemical_name_systematic
;
(E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-
1H-1,2,4-triazole-5(4H)-thione
N,N-dimethylformamide solvate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.8200(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.23740(10)
_cell_length_b                   23.4970(4)
_cell_length_c                   10.8214(2)
_cell_measurement_reflns_used    5142
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      2.63
_cell_volume                     1751.97(5)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27543
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.9622
_exptl_absorpt_correction_T_min  0.9121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.187
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0578P)²+0.3261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                2909
_reflns_number_total             5088
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2959.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224362
_cod_database_fobs_code          2224362
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.62071(9) 0.36346(2) 0.02621(6) 0.0699(2) Uani d . 1 . .
O O1 0.9054(2) 0.46985(6) 0.34539(13) 0.0699(4) Uani d . 1 . .
N N1 1.0341(2) 0.55794(7) 0.39613(17) 0.0555(4) Uani d . 1 . .
N N2 0.7262(2) 0.50131(6) -0.03966(15) 0.0485(4) Uani d . 1 . .
N N3 0.6254(2) 0.45953(6) -0.12480(14) 0.0452(3) Uani d . 1 . .
N N4 0.4855(2) 0.38697(7) -0.22893(17) 0.0554(4) Uani d . 1 . .
N N5 0.4700(2) 0.42818(7) -0.32108(16) 0.0586(4) Uani d . 1 . .
C C1 0.9416(3) 0.51769(8) 0.30855(19) 0.0534(5) Uani d . 1 . .
C C2 1.0822(3) 0.61175(8) 0.36456(19) 0.0510(4) Uani d . 1 . .
C C3 1.1770(3) 0.65002(9) 0.4618(2) 0.0641(5) Uani d . 1 . .
H H3A 1.2079 0.6397 0.5488 0.077 Uiso calc R 1 . .
C C4 1.2241(3) 0.70310(9) 0.4275(2) 0.0698(6) Uani d . 1 . .
H H4A 1.2854 0.7290 0.4920 0.084 Uiso calc R 1 . .
C C5 1.1817(3) 0.71879(9) 0.2983(3) 0.0680(6) Uani d . 1 . .
H H5A 1.2162 0.7547 0.2769 0.082 Uiso calc R 1 . .
C C6 1.0893(3) 0.68142(8) 0.2023(2) 0.0617(5) Uani d . 1 . .
H H6A 1.0612 0.6922 0.1157 0.074 Uiso calc R 1 . .
C C7 1.0366(3) 0.62699(8) 0.23332(19) 0.0497(4) Uani d . 1 . .
C C8 0.9380(3) 0.58604(8) 0.13906(19) 0.0505(4) Uani d . 1 . .
H H8A 0.9049 0.5956 0.0516 0.061 Uiso calc R 1 . .
C C9 0.8906(3) 0.53351(7) 0.17255(17) 0.0472(4) Uani d . 1 . .
C C10 0.7858(3) 0.49056(8) 0.07984(19) 0.0526(5) Uani d . 1 . .
H H10A 0.7630 0.4549 0.1095 0.063 Uiso calc R 1 . .
C C11 0.5783(2) 0.40326(7) -0.10719(19) 0.0485(4) Uani d . 1 . .
C C12 0.5562(3) 0.47203(8) -0.25541(19) 0.0516(4) Uani d . 1 . .
C C13 0.5759(3) 0.52850(9) -0.3093(2) 0.0685(6) Uani d . 1 . .
H H13A 0.5120 0.5284 -0.4012 0.103 Uiso calc R 1 . .
H H13B 0.7109 0.5372 -0.2928 0.103 Uiso calc R 1 . .
H H13C 0.5175 0.5567 -0.2690 0.103 Uiso calc R 1 . .
O O2 0.3433(2) 0.27901(6) 0.71425(18) 0.0801(5) Uani d . 1 . .
N N6 0.2576(2) 0.19916(7) 0.79911(17) 0.0606(4) Uani d . 1 . .
C C14 0.3236(3) 0.25191(9) 0.8062(2) 0.0645(6) Uani d . 1 . .
H H14A 0.3576 0.2697 0.8867 0.077 Uiso calc R 1 . .
C C15 0.1949(4) 0.17088(10) 0.6743(2) 0.0841(7) Uani d . 1 . .
H H15A 0.1598 0.1988 0.6065 0.126 Uiso calc R 1 . .
H H15B 0.0847 0.1473 0.6696 0.126 Uiso calc R 1 . .
H H15C 0.2987 0.1478 0.6643 0.126 Uiso calc R 1 . .
C C16 0.2369(5) 0.16951(13) 0.9100(3) 0.1056(10) Uani d . 1 . .
H H16A 0.2538 0.1957 0.9806 0.158 Uiso calc R 1 . .
H H16B 0.3333 0.1401 0.9350 0.158 Uiso calc R 1 . .
H H16C 0.1099 0.1528 0.8886 0.158 Uiso calc R 1 . .
H H1N1 1.054(3) 0.5478(9) 0.482(2) 0.063(6) Uiso d . 1 . .
H H1N4 0.436(3) 0.3526(10) -0.249(2) 0.070(7) Uiso d . 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 124.83(18) ?
C1 N1 H1N1 . . 114.3(13) ?
C2 N1 H1N1 . . 120.6(13) ?
C10 N2 N3 . . 119.03(16) ?
C12 N3 N2 . . 118.77(15) ?
C12 N3 C11 . . 108.36(15) ?
N2 N3 C11 . . 132.85(15) ?
C11 N4 N5 . . 114.79(16) ?
C11 N4 H1N4 . . 123.0(15) ?
N5 N4 H1N4 . . 122.2(15) ?
C12 N5 N4 . . 104.12(16) ?
O1 C1 N1 . . 120.69(18) ?
O1 C1 C9 . . 122.81(17) ?
N1 C1 C9 . . 116.50(17) ?
N1 C2 C3 . . 120.42(19) ?
N1 C2 C7 . . 119.00(17) ?
C3 C2 C7 . . 120.58(18) ?
C4 C3 C2 . . 119.1(2) ?
C4 C3 H3A . . 120.4 ?
C2 C3 H3A . . 120.4 ?
C3 C4 C5 . . 121.2(2) ?
C3 C4 H4A . . 119.4 ?
C5 C4 H4A . . 119.4 ?
C6 C5 C4 . . 120.1(2) ?
C6 C5 H5A . . 120.0 ?
C4 C5 H5A . . 120.0 ?
C5 C6 C7 . . 120.5(2) ?
C5 C6 H6A . . 119.7 ?
C7 C6 H6A . . 119.7 ?
C2 C7 C6 . . 118.54(18) ?
C2 C7 C8 . . 117.62(17) ?
C6 C7 C8 . . 123.84(19) ?
C9 C8 C7 . . 122.29(18) ?
C9 C8 H8A . . 118.9 ?
C7 C8 H8A . . 118.9 ?
C8 C9 C1 . . 119.75(17) ?
C8 C9 C10 . . 124.36(17) ?
C1 C9 C10 . . 115.88(16) ?
N2 C10 C9 . . 120.68(17) ?
N2 C10 H10A . . 119.7 ?
C9 C10 H10A . . 119.7 ?
N4 C11 N3 . . 101.93(16) ?
N4 C11 S1 . . 126.57(14) ?
N3 C11 S1 . . 131.50(14) ?
N5 C12 N3 . . 110.81(17) ?
N5 C12 C13 . . 125.92(18) ?
N3 C12 C13 . . 123.26(17) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C14 N6 C16 . . 122.4(2) ?
C14 N6 C15 . . 119.25(19) ?
C16 N6 C15 . . 118.30(19) ?
O2 C14 N6 . . 124.8(2) ?
O2 C14 H14A . . 117.6 ?
N6 C14 H14A . . 117.6 ?
N6 C15 H15A . . 109.5 ?
N6 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N6 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N6 C16 H16A . . 109.5 ?
N6 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N6 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C11 . 1.668(2) ?
O1 C1 . 1.247(2) ?
N1 C1 . 1.361(2) ?
N1 C2 . 1.382(2) ?
N1 H1N1 . 0.93(2) ?
N2 C10 . 1.257(2) ?
N2 N3 . 1.3903(19) ?
N3 C12 . 1.379(2) ?
N3 C11 . 1.393(2) ?
N4 C11 . 1.338(2) ?
N4 N5 . 1.370(2) ?
N4 H1N4 . 0.88(2) ?
N5 C12 . 1.298(2) ?
C1 C9 . 1.452(3) ?
C2 C3 . 1.395(3) ?
C2 C7 . 1.403(3) ?
C3 C4 . 1.374(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.386(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.369(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.405(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.425(2) ?
C8 C9 . 1.359(2) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.461(2) ?
C10 H10A . 0.9300 ?
C12 C13 . 1.474(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
O2 C14 . 1.225(3) ?
N6 C14 . 1.322(3) ?
N6 C16 . 1.434(3) ?
N6 C15 . 1.448(3) ?
C14 H14A . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N1 O1 3_766 0.93(2) 1.85(2) 2.774(2) 178(2) yes
N4 H1N4 O2 1_554 0.88(2) 1.85(2) 2.736(2) 177.2(14) yes
C10 H10A S1 . 0.9300 2.4300 3.203(2) 140.00 yes
C16 H16A O2 4_566 0.9600 2.4800 3.368(4) 153.00 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 N2 N3 C12 . . . . 178.43(17) ?
C10 N2 N3 C11 . . . . -3.3(3) ?
C11 N4 N5 C12 . . . . 0.1(2) ?
C2 N1 C1 O1 . . . . 179.27(18) ?
C2 N1 C1 C9 . . . . -0.2(3) ?
C1 N1 C2 C3 . . . . 179.90(18) ?
C1 N1 C2 C7 . . . . -0.9(3) ?
N1 C2 C3 C4 . . . . 179.58(19) ?
C7 C2 C3 C4 . . . . 0.4(3) ?
C2 C3 C4 C5 . . . . -1.0(3) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
C4 C5 C6 C7 . . . . 0.0(3) ?
N1 C2 C7 C6 . . . . -178.83(17) ?
C3 C2 C7 C6 . . . . 0.3(3) ?
N1 C2 C7 C8 . . . . 1.4(3) ?
C3 C2 C7 C8 . . . . -179.39(16) ?
C5 C6 C7 C2 . . . . -0.5(3) ?
C5 C6 C7 C8 . . . . 179.16(18) ?
C2 C7 C8 C9 . . . . -0.9(3) ?
C6 C7 C8 C9 . . . . 179.39(18) ?
C7 C8 C9 C1 . . . . -0.2(3) ?
C7 C8 C9 C10 . . . . 178.53(16) ?
O1 C1 C9 C8 . . . . -178.68(18) ?
N1 C1 C9 C8 . . . . 0.8(3) ?
O1 C1 C9 C10 . . . . 2.5(3) ?
N1 C1 C9 C10 . . . . -178.08(16) ?
N3 N2 C10 C9 . . . . -179.39(15) ?
C8 C9 C10 N2 . . . . -2.6(3) ?
C1 C9 C10 N2 . . . . 176.18(17) ?
N5 N4 C11 N3 . . . . -0.2(2) ?
N5 N4 C11 S1 . . . . 179.90(13) ?
C12 N3 C11 N4 . . . . 0.18(18) ?
N2 N3 C11 N4 . . . . -178.25(16) ?
C12 N3 C11 S1 . . . . -179.91(15) ?
N2 N3 C11 S1 . . . . 1.7(3) ?
N4 N5 C12 N3 . . . . 0.0(2) ?
N4 N5 C12 C13 . . . . -178.53(19) ?
N2 N3 C12 N5 . . . . 178.56(15) ?
C11 N3 C12 N5 . . . . -0.1(2) ?
N2 N3 C12 C13 . . . . -2.9(3) ?
C11 N3 C12 C13 . . . . 178.46(18) ?
C16 N6 C14 O2 . . . . -179.8(2) ?
C15 N6 C14 O2 . . . . -2.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655956
