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#$Date: 2021-02-05 01:02:52 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261623 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241492.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_7241492
loop_
_publ_author_name
'Wzgarda-Raj, Kinga'
'Palusiak, Marcin'
'Wojtulewski, Sławomir'
'Rybarczyk-Pirek, Agnieszka J.'
_publ_section_title
;
 The role of sulfur interactions in crystal architecture: experimental and
 quantum theoretical studies on hydrogen, halogen, and chalcogen bonds in
 trithiocyanuric acid--pyridine N-oxide co-crystals
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              324
_journal_page_last               334
_journal_paper_doi               10.1039/D0CE01319F
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C3 H3 N3 S3, C5 H5 N O'
_chemical_formula_sum            'C8 H8 N4 O S3'
_chemical_formula_weight         272.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-06-21 deposited with the CCDC.	2020-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.154(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.0734(4)
_cell_length_b                   4.45460(10)
_cell_length_c                   22.9310(4)
_cell_measurement_reflns_used    14615
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3670
_cell_measurement_theta_min      3.8430
_cell_volume                     2245.65(8)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4052
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method
;
CrysAlisPro 1.171.39.15e (Rigaku Oxford Diffraction, 2015)
;
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20354
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.497
_diffrn_reflns_theta_min         3.871
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.925
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00054(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0233
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0369P)²+2.4173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0622
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2060
_reflns_number_total             2079
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01319f2.cif
_cod_data_source_block           structure_I
_cod_depositor_comments
'Adding full bibliography for 7241492--7241495.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7241492
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S6 S 0.58393(2) 1.13535(8) 0.46454(2) 0.01676(11) Uani 1 1 d . . . . .
S4 S 0.75226(2) 0.44067(8) 0.57287(2) 0.01914(12) Uani 1 1 d . . . . .
S2 S 0.52795(2) 0.43679(8) 0.63763(2) 0.02046(12) Uani 1 1 d . . . . .
O11 O 0.66406(5) 0.0188(2) 0.67293(4) 0.0214(2) Uani 1 1 d . . . . .
N3 N 0.63793(5) 0.4600(3) 0.59947(5) 0.0159(2) Uani 1 1 d . . . . .
N5 N 0.66282(5) 0.7855(3) 0.52669(5) 0.0161(2) Uani 1 1 d . . . . .
N1 N 0.56549(5) 0.7771(3) 0.55395(5) 0.0163(2) Uani 1 1 d . . . . .
N11 N 0.65161(5) 0.1083(3) 0.72600(5) 0.0175(2) Uani 1 1 d . . . . .
C2 C 0.57965(6) 0.5625(3) 0.59580(6) 0.0160(3) Uani 1 1 d . . . . .
C4 C 0.68139(6) 0.5674(3) 0.56640(6) 0.0159(3) Uani 1 1 d . . . . .
C6 C 0.60467(6) 0.8895(3) 0.51712(6) 0.0153(3) Uani 1 1 d . . . . .
C12 C 0.68797(6) 0.3139(3) 0.75482(6) 0.0215(3) Uani 1 1 d . . . . .
C16 C 0.60351(7) -0.0094(3) 0.75037(7) 0.0206(3) Uani 1 1 d . . . . .
C15 C 0.59172(7) 0.0759(3) 0.80615(7) 0.0232(3) Uani 1 1 d . . . . .
C14 C 0.62887(7) 0.2830(4) 0.83677(6) 0.0248(3) Uani 1 1 d . . . . .
C13 C 0.67764(7) 0.4019(4) 0.81057(7) 0.0249(3) Uani 1 1 d . . . . .
H3 H 0.6483(9) 0.316(5) 0.6266(9) 0.030 Uiso 1 1 d . U . . .
H5 H 0.6887(9) 0.851(5) 0.5031(9) 0.030 Uiso 1 1 d . U . . .
H1 H 0.5296(10) 0.835(5) 0.5491(8) 0.030 Uiso 1 1 d . U . . .
H12 H 0.7192(9) 0.388(4) 0.7346(9) 0.030 Uiso 1 1 d . U . . .
H16 H 0.5812(9) -0.150(5) 0.7269(8) 0.030 Uiso 1 1 d . U . . .
H15 H 0.5595(9) -0.015(5) 0.8234(9) 0.030 Uiso 1 1 d . U . . .
H14 H 0.6201(9) 0.340(4) 0.8748(9) 0.030 Uiso 1 1 d . U . . .
H13 H 0.7047(9) 0.540(5) 0.8296(9) 0.030 Uiso 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
C2 N3 C4 123.84(12) . . ?
C2 N3 H3 117.3(12) . . ?
C4 N3 H3 118.9(12) . . ?
C6 N5 C4 124.70(12) . . ?
C6 N5 H5 116.5(13) . . ?
C4 N5 H5 118.5(13) . . ?
C6 N1 C2 125.10(12) . . ?
C6 N1 H1 117.0(14) . . ?
C2 N1 H1 117.7(14) . . ?
O11 N11 C16 119.77(12) . . ?
O11 N11 C12 119.18(12) . . ?
C16 N11 C12 121.05(13) . . ?
N3 C2 N1 115.61(12) . . ?
N3 C2 S2 123.26(11) . . ?
N1 C2 S2 121.12(10) . . ?
N3 C4 N5 115.85(12) . . ?
N3 C4 S4 122.47(11) . . ?
N5 C4 S4 121.67(10) . . ?
N1 C6 N5 114.69(12) . . ?
N1 C6 S6 123.01(10) . . ?
N5 C6 S6 122.30(10) . . ?
N11 C12 C13 120.48(14) . . ?
N11 C12 H12 115.7(12) . . ?
C13 C12 H12 123.8(12) . . ?
N11 C16 C15 119.83(14) . . ?
N11 C16 H16 114.4(12) . . ?
C15 C16 H16 125.7(12) . . ?
C16 C15 C14 120.08(14) . . ?
C16 C15 H15 119.0(12) . . ?
C14 C15 H15 120.9(12) . . ?
C15 C14 C13 118.92(14) . . ?
C15 C14 H14 119.1(12) . . ?
C13 C14 H14 122.0(12) . . ?
C12 C13 C14 119.63(15) . . ?
C12 C13 H13 117.9(12) . . ?
C14 C13 H13 122.4(12) . . ?
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
S6 C6 1.6624(14) . ?
S4 C4 1.6571(14) . ?
S2 C2 1.6530(14) . ?
O11 N11 1.3324(15) . ?
N3 C2 1.3608(18) . ?
N3 C4 1.3620(18) . ?
N3 H3 0.91(2) . ?
N5 C6 1.3637(18) . ?
N5 C4 1.3690(18) . ?
N5 H5 0.87(2) . ?
N1 C6 1.3575(18) . ?
N1 C2 1.3706(18) . ?
N1 H1 0.83(2) . ?
N11 C16 1.3494(19) . ?
N11 C12 1.3506(19) . ?
C12 C13 1.376(2) . ?
C12 H12 0.93(2) . ?
C16 C15 1.381(2) . ?
C16 H16 0.94(2) . ?
C15 C14 1.383(2) . ?
C15 H15 0.94(2) . ?
C14 C13 1.385(2) . ?
C14 H14 0.94(2) . ?
C13 H13 0.94(2) . ?
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
N3 H3 O11 0.91(2) 1.71(2) 2.6188(16) 174.3(19) . 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
C4 N3 C2 N1 2.94(19) . . . . ?
C4 N3 C2 S2 -178.12(10) . . . . ?
C6 N1 C2 N3 0.1(2) . . . . ?
C6 N1 C2 S2 -178.87(10) . . . . ?
C2 N3 C4 N5 -1.79(19) . . . . ?
C2 N3 C4 S4 178.96(10) . . . . ?
C6 N5 C4 N3 -2.58(19) . . . . ?
C6 N5 C4 S4 176.68(10) . . . . ?
C2 N1 C6 N5 -3.89(19) . . . . ?
C2 N1 C6 S6 176.31(10) . . . . ?
C4 N5 C6 N1 5.20(19) . . . . ?
C4 N5 C6 S6 -175.00(10) . . . . ?
O11 N11 C12 C13 -177.48(13) . . . . ?
C16 N11 C12 C13 1.8(2) . . . . ?
O11 N11 C16 C15 177.89(13) . . . . ?
C12 N11 C16 C15 -1.4(2) . . . . ?
N11 C16 C15 C14 0.5(2) . . . . ?
C16 C15 C14 C13 0.0(2) . . . . ?
N11 C12 C13 C14 -1.3(2) . . . . ?
C15 C14 C13 C12 0.4(2) . . . . ?
