#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:02:52 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261623 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241495.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_7241495
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         '2(C5 H4 N2 O3), C3 H3 N3 S3'
_chemical_formula_sum            'C13 H11 N7 O6 S3'
_chemical_formula_weight         457.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/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                 108.580(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0067(3)
_cell_length_b                   4.55910(10)
_cell_length_c                   24.5193(3)
_cell_measurement_reflns_used    9526
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2880
_cell_measurement_theta_min      4.2330
_cell_volume                     1802.02(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(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  0.0265
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18033
_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         68.458
_diffrn_reflns_theta_min         2.741
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77185
_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    1.686
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0397P)²+0.6410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3096
_reflns_number_total             3338
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01319f2.cif
_cod_data_source_block           structure_II
_cod_depositor_comments
'Adding full bibliography for 7241492--7241495.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7241495
_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+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_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
S4 S 0.21810(2) 0.93188(8) 0.04872(2) 0.01612(10) Uani 1 1 d . . . . .
S6 S -0.01745(2) 0.22469(8) 0.06858(2) 0.01724(10) Uani 1 1 d . . . . .
S2 S 0.27519(2) 0.22591(8) 0.22887(2) 0.01777(10) Uani 1 1 d . . . . .
O11B O 0.40053(6) 0.6955(2) 0.17606(4) 0.0161(2) Uani 1 1 d . . . . .
O11A O 0.06154(6) 0.0305(3) 0.22360(4) 0.0239(2) Uani 1 1 d . . . . .
O42B O 0.62777(6) -0.2587(2) 0.12849(4) 0.0210(2) Uani 1 1 d . . . . .
41B O 0.53190(7) -0.2443(2) 0.04523(4) 0.0222(2) Uani 1 1 d . . . . .
O42A O 0.32918(7) -0.2860(3) 0.45274(4) 0.0235(2) Uani 1 1 d . . . . .
O41A O 0.27595(7) 0.1048(3) 0.47726(4) 0.0242(2) Uani 1 1 d . . . . .
N3 N 0.23597(7) 0.5733(3) 0.13728(5) 0.0134(2) Uani 1 1 d . . . . .
N1 N 0.12983(7) 0.2840(3) 0.14793(5) 0.0145(2) Uani 1 1 d . . . . .
N11B N 0.43803(7) 0.4880(3) 0.15678(4) 0.0132(2) Uani 1 1 d . . . . .
N5 N 0.10784(7) 0.5678(3) 0.06688(5) 0.0144(2) Uani 1 1 d . . . . .
N14B N 0.56248(7) -0.1615(3) 0.09480(5) 0.0159(2) Uani 1 1 d . . . . .
N11A N 0.10910(7) -0.0137(3) 0.27697(5) 0.0173(2) Uani 1 1 d . . . . .
N14A N 0.27843(7) -0.0861(3) 0.44283(5) 0.0169(2) Uani 1 1 d . . . . .
C14B C 0.51881(8) 0.0656(3) 0.11656(6) 0.0149(3) Uani 1 1 d . . . . .
C14A C 0.21630(8) -0.0715(3) 0.38539(5) 0.0150(3) Uani 1 1 d . . . . .
C16B C 0.40657(8) 0.3963(3) 0.10107(6) 0.0162(3) Uani 1 1 d . . . . .
C13A C 0.15089(9) 0.1221(3) 0.37532(6) 0.0175(3) Uani 1 1 d . . . . .
C12B C 0.50900(8) 0.3678(3) 0.19269(5) 0.0154(3) Uani 1 1 d . . . . .
C15B C 0.44621(9) 0.1826(3) 0.08009(6) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.21156(8) 0.3670(3) 0.16878(5) 0.0136(3) Uani 1 1 d . . . . .
C6 C 0.07679(8) 0.3654(3) 0.09536(5) 0.0139(3) Uani 1 1 d . . . . .
C16A C 0.17057(9) -0.2155(3) 0.28779(6) 0.0190(3) Uani 1 1 d . . . . .
C13B C 0.55088(8) 0.1561(3) 0.17331(6) 0.0162(3) Uani 1 1 d . . . . .
C12A C 0.09677(9) 0.1470(3) 0.32017(6) 0.0186(3) Uani 1 1 d . . . . .
C4 C 0.18638(8) 0.6831(3) 0.08590(5) 0.0136(3) Uani 1 1 d . . . . .
C15A C 0.22582(9) -0.2484(3) 0.34232(6) 0.0172(3) Uani 1 1 d . . . . .
H3 H 0.2859(13) 0.629(4) 0.1485(8) 0.021 Uiso 1 1 d . U . . .
H1 H 0.1123(12) 0.185(4) 0.1686(8) 0.021 Uiso 1 1 d . U . . .
H5 H 0.0761(12) 0.621(4) 0.0325(8) 0.021 Uiso 1 1 d . U . . .
H16B H 0.3588(12) 0.494(4) 0.0786(8) 0.021 Uiso 1 1 d . U . . .
H13A H 0.1419(12) 0.240(4) 0.4039(8) 0.021 Uiso 1 1 d . U . . .
H12B H 0.5253(11) 0.442(4) 0.2311(8) 0.021 Uiso 1 1 d . U . . .
H15B H 0.4263(12) 0.124(4) 0.0425(8) 0.021 Uiso 1 1 d . U . . .
H16A H 0.1727(12) -0.321(4) 0.2567(8) 0.021 Uiso 1 1 d . U . . .
H13B H 0.5979(12) 0.069(4) 0.1985(8) 0.021 Uiso 1 1 d . U . . .
H12A H 0.0516(12) 0.277(4) 0.3105(8) 0.021 Uiso 1 1 d . U . . .
H15A H 0.2693(12) -0.383(4) 0.3477(7) 0.021 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 124.38(12) . . ?
C6 N1 C2 124.16(12) . . ?
O11B N11B C12B 119.35(11) . . ?
O11B N11B C16B 120.11(11) . . ?
C12B N11B C16B 120.53(12) . . ?
C6 N5 C4 125.48(12) . . ?
41B N14B O42B 124.20(13) . . ?
41B N14B C14B 118.39(11) . . ?
O42B N14B C14B 117.41(11) . . ?
O11A N11A C16A 119.38(12) . . ?
O11A N11A C12A 119.59(13) . . ?
C16A N11A C12A 121.02(12) . . ?
O41A N14A O42A 124.73(12) . . ?
O41A N14A C14A 117.22(12) . . ?
O42A N14A C14A 118.04(12) . . ?
C15B C14B C13B 121.35(14) . . ?
C15B C14B N14B 119.21(12) . . ?
C13B C14B N14B 119.44(12) . . ?
C15A C14A C13A 121.48(13) . . ?
C15A C14A N14A 118.93(13) . . ?
C13A C14A N14A 119.58(12) . . ?
N11B C16B C15B 120.62(13) . . ?
C12A C13A C14A 118.51(13) . . ?
N11B C12B C13B 120.68(12) . . ?
C16B C15B C14B 118.39(13) . . ?
N3 C2 N1 115.74(12) . . ?
N3 C2 S2 122.80(10) . . ?
N1 C2 S2 121.45(10) . . ?
N5 C6 N1 114.84(12) . . ?
N5 C6 S6 122.96(10) . . ?
N1 C6 S6 122.19(11) . . ?
N11A C16A C15A 120.68(13) . . ?
C12B C13B C14B 118.41(13) . . ?
N11A C12A C13A 120.03(14) . . ?
N3 C4 N5 114.87(12) . . ?
N3 C4 S4 123.11(10) . . ?
N5 C4 S4 122.01(10) . . ?
C16A C15A C14A 118.04(14) . . ?
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
S4 C4 1.6499(14) . ?
S6 C6 1.6556(14) . ?
S2 C2 1.6551(13) . ?
O11B N11B 1.3104(16) . ?
O11A N11A 1.3163(15) . ?
O42B N14B 1.2358(17) . ?
41B N14B 1.2196(16) . ?
O42A N14A 1.2253(17) . ?
O41A N14A 1.2224(17) . ?
N3 C2 1.3630(18) . ?
N3 C4 1.3681(18) . ?
N1 C6 1.3683(17) . ?
N1 C2 1.3725(18) . ?
N11B C12B 1.3620(18) . ?
N11B C16B 1.3642(18) . ?
N5 C6 1.3610(18) . ?
N5 C4 1.3716(18) . ?
N14B C14B 1.4699(18) . ?
N11A C16A 1.354(2) . ?
N11A C12A 1.358(2) . ?
N14A C14A 1.4685(17) . ?
C14B C15B 1.380(2) . ?
C14B C13B 1.3856(19) . ?
C14A C15A 1.379(2) . ?
C14A C13A 1.379(2) . ?
C16B C15B 1.375(2) . ?
C13A C12A 1.377(2) . ?
C12B C13B 1.371(2) . ?
C16A C15A 1.376(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 O11B 0.84(2) 1.87(2) 2.7112(15) 172(2) . yes
N1 H1 O11A 0.80(2) 1.95(2) 2.7386(15) 167(2) . 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
41B N14B C14B C15B -1.61(19) . . . . ?
O42B N14B C14B C15B 179.19(12) . . . . ?
41B N14B C14B C13B 177.84(12) . . . . ?
O42B N14B C14B C13B -1.36(19) . . . . ?
O41A N14A C14A C15A 168.42(13) . . . . ?
O42A N14A C14A C15A -11.08(19) . . . . ?
O41A N14A C14A C13A -10.26(19) . . . . ?
O42A N14A C14A C13A 170.24(13) . . . . ?
O11B N11B C16B C15B 178.81(12) . . . . ?
C12B N11B C16B C15B -0.4(2) . . . . ?
C15A C14A C13A C12A -3.2(2) . . . . ?
N14A C14A C13A C12A 175.40(12) . . . . ?
O11B N11B C12B C13B -178.19(12) . . . . ?
C16B N11B C12B C13B 1.1(2) . . . . ?
N11B C16B C15B C14B -0.6(2) . . . . ?
C13B C14B C15B C16B 1.0(2) . . . . ?
N14B C14B C15B C16B -179.51(12) . . . . ?
C4 N3 C2 N1 -4.39(19) . . . . ?
C4 N3 C2 S2 176.35(10) . . . . ?
C6 N1 C2 N3 8.8(2) . . . . ?
C6 N1 C2 S2 -171.90(11) . . . . ?
C4 N5 C6 N1 2.1(2) . . . . ?
C4 N5 C6 S6 -177.30(11) . . . . ?
C2 N1 C6 N5 -7.7(2) . . . . ?
C2 N1 C6 S6 171.71(11) . . . . ?
O11A N11A C16A C15A 174.23(13) . . . . ?
C12A N11A C16A C15A -4.6(2) . . . . ?
N11B C12B C13B C14B -0.6(2) . . . . ?
C15B C14B C13B C12B -0.4(2) . . . . ?
N14B C14B C13B C12B -179.89(12) . . . . ?
O11A N11A C12A C13A -173.93(13) . . . . ?
C16A N11A C12A C13A 4.9(2) . . . . ?
C14A C13A C12A N11A -1.0(2) . . . . ?
C2 N3 C4 N5 -0.52(19) . . . . ?
C2 N3 C4 S4 -179.71(10) . . . . ?
C6 N5 C4 N3 1.74(19) . . . . ?
C6 N5 C4 S4 -179.07(11) . . . . ?
N11A C16A C15A C14A 0.4(2) . . . . ?
C13A C14A C15A C16A 3.5(2) . . . . ?
N14A C14A C15A C16A -175.11(13) . . . . ?
