#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/41/7224174.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_7224174
loop_
_publ_author_name
'Taouss, Christina'
'Döring, Cindy'
'Jones, Peter G.'
'Pinkert, Lukas'
'Strey, Mark'
_publ_section_title
;
 Single crystals that spontaneously spawn other single crystals: a ternary
 and a binary adduct of thiourea and 2,5-dimethylpyrazine
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1842
_journal_paper_doi               10.1039/C6CE00100A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C22 H40 N14 S4'
_chemical_formula_weight         628.92
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-01-04 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                89.976(4)
_cell_angle_beta                 83.248(3)
_cell_angle_gamma                85.245(3)
_cell_formula_units_Z            1
_cell_length_a                   7.9939(2)
_cell_length_b                   9.0331(4)
_cell_length_c                   11.1337(5)
_cell_measurement_reflns_used    16367
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.7500
_cell_measurement_theta_min      2.8890
_cell_volume                     795.60(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            60506
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         31.05
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0364P)²+0.3936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                4081
_reflns_number_total             4780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce00100a2.cif
_cod_data_source_block           luke
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7224174--7224176.cif.
;
_cod_database_code               7224174
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.62504(4) 0.84409(4) 0.13066(3) 0.01630(8) Uani 1 1 d .
N1 N 0.36274(16) 1.04634(13) 0.16335(11) 0.0189(2) Uani 1 1 d .
H01 H 0.281(2) 1.096(2) 0.2048(17) 0.028(5) Uiso 1 1 d .
H02 H 0.384(2) 1.066(2) 0.0891(17) 0.026(5) Uiso 1 1 d .
C2 C 0.45619(17) 0.94002(14) 0.21296(11) 0.0155(2) Uani 1 1 d .
N3 N 0.41490(16) 0.91166(14) 0.33006(11) 0.0197(2) Uani 1 1 d .
H03 H 0.330(2) 0.960(2) 0.3684(17) 0.030(5) Uiso 1 1 d .
H04 H 0.470(2) 0.844(2) 0.3657(17) 0.028(5) Uiso 1 1 d .
S2 S 0.05360(4) 1.17694(3) 0.37206(3) 0.01550(8) Uani 1 1 d .
N4 N -0.14783(16) 0.95870(14) 0.35859(11) 0.0211(2) Uani 1 1 d .
H05 H -0.212(2) 0.908(2) 0.3221(16) 0.025(4) Uiso 1 1 d .
H06 H -0.120(2) 0.931(2) 0.4267(17) 0.027(5) Uiso 1 1 d .
C5 C -0.07512(16) 1.07116(14) 0.30238(11) 0.0145(2) Uani 1 1 d .
N6 N -0.10694(16) 1.09963(13) 0.18966(11) 0.0191(2) Uani 1 1 d .
H07 H -0.170(2) 1.043(2) 0.1531(17) 0.029(5) Uiso 1 1 d .
H08 H -0.064(2) 1.176(2) 0.1511(17) 0.033(5) Uiso 1 1 d .
N11 N 0.66580(15) 0.48310(13) 0.67659(10) 0.0191(2) Uani 1 1 d .
C12 C 0.55185(17) 0.59893(15) 0.70444(12) 0.0171(3) Uani 1 1 d .
C13 C 0.51737(17) 0.70360(15) 0.61692(12) 0.0178(3) Uani 1 1 d .
H13 H 0.4343 0.7835 0.6385 0.021 Uiso 1 1 calc R
N14 N 0.59621(14) 0.69679(12) 0.50347(10) 0.0167(2) Uani 1 1 d .
C15 C 0.71232(16) 0.58234(14) 0.47656(11) 0.0152(2) Uani 1 1 d .
C16 C 0.74373(18) 0.47613(15) 0.56397(12) 0.0181(3) Uani 1 1 d .
H16 H 0.8247 0.3948 0.5421 0.022 Uiso 1 1 calc R
C17 C 0.46509(19) 0.60864(17) 0.83158(12) 0.0235(3) Uani 1 1 d .
H17A H 0.4314 0.5105 0.8570 0.035 Uiso 1 1 calc R
H17B H 0.3646 0.6792 0.8351 0.035 Uiso 1 1 calc R
H17C H 0.5426 0.6426 0.8856 0.035 Uiso 1 1 calc R
C18 C 0.80799(18) 0.57164(15) 0.35250(12) 0.0199(3) Uani 1 1 d .
H18A H 0.7341 0.6099 0.2933 0.030 Uiso 1 1 calc R
H18B H 0.8465 0.4676 0.3334 0.030 Uiso 1 1 calc R
H18C H 0.9060 0.6305 0.3496 0.030 Uiso 1 1 calc R
N21 N 0.00021(14) 1.35967(12) 0.05160(10) 0.0157(2) Uani 1 1 d .
C22 C -0.07309(16) 1.38822(14) -0.04930(11) 0.0143(2) Uani 1 1 d .
C23 C 0.07204(16) 1.47053(14) 0.09957(11) 0.0151(2) Uani 1 1 d .
H23 H 0.1246 1.4523 0.1710 0.018 Uiso 1 1 calc R
C24 C -0.15370(19) 1.26459(15) -0.10422(12) 0.0198(3) Uani 1 1 d .
H24A H -0.0707 1.1786 -0.1196 0.030 Uiso 1 1 calc R
H24B H -0.1933 1.2978 -0.1806 0.030 Uiso 1 1 calc R
H24C H -0.2498 1.2366 -0.0484 0.030 Uiso 1 1 calc R
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'
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_3
N1 C2 N3 117.61(13) . .
N1 C2 S1 121.30(10) . .
N3 C2 S1 121.09(10) . .
N6 C5 N4 117.65(12) . .
N6 C5 S2 120.75(10) . .
N4 C5 S2 121.60(10) . .
C16 N11 C12 116.87(12) . .
N11 C12 C13 120.13(12) . .
N11 C12 C17 117.20(12) . .
C13 C12 C17 122.66(12) . .
N14 C13 C12 122.99(12) . .
C15 N14 C13 116.71(11) . .
N14 C15 C16 120.00(12) . .
N14 C15 C18 119.03(12) . .
C16 C15 C18 120.97(12) . .
N11 C16 C15 123.26(12) . .
C23 N21 C22 117.48(11) . .
N21 C22 C23 119.75(11) . 2_585
N21 C22 C24 117.99(11) . .
C23 C22 C24 122.26(11) 2_585 .
N21 C23 C22 122.77(11) . 2_585
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.7113(13) .
N1 C2 1.3278(17) .
C2 N3 1.3367(17) .
S2 C5 1.7103(13) .
N4 C5 1.3316(17) .
C5 N6 1.3304(17) .
N11 C16 1.3319(18) .
N11 C12 1.3404(18) .
C12 C13 1.3923(19) .
C12 C17 1.5005(18) .
C13 N14 1.3427(17) .
N14 C15 1.3400(17) .
C15 C16 1.3955(18) .
C15 C18 1.4972(18) .
N21 C23 1.3363(16) .
N21 C22 1.3421(16) .
C22 C23 1.3933(17) 2_585
C22 C24 1.4997(18) .
C23 C22 1.3933(17) 2_585
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
N1 H01 S2 0.85(2) 2.51(2) 3.3267(13) 162.1(17) .
N1 H02 S1 0.847(19) 2.583(19) 3.4121(13) 166.5(16) 2_675
N3 H03 S2 0.85(2) 2.83(2) 3.5831(13) 150.0(16) .
N3 H04 N14 0.85(2) 2.30(2) 3.1280(17) 165.9(17) .
N4 H05 S1 0.855(19) 2.709(19) 3.4937(13) 153.1(15) 1_455
N4 H06 S2 0.847(19) 2.539(19) 3.3819(13) 173.8(17) 2_576
N6 H07 S1 0.877(19) 2.56(2) 3.3915(13) 157.8(16) 1_455
N6 H08 N21 0.89(2) 2.06(2) 2.9385(16) 171.4(18) .
C23 H23 N11 0.95 2.62 3.4862(17) 151.9 2_676
C24 H24B N11 0.98 2.59 3.5050(18) 155.5 1_464
C18 H18A S1 0.98 2.93 3.8136(14) 150.7 .
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_4
C16 N11 C12 C13 1.14(19) .
C16 N11 C12 C17 -179.24(12) .
N11 C12 C13 N14 -1.4(2) .
C17 C12 C13 N14 179.03(13) .
C12 C13 N14 C15 0.13(19) .
C13 N14 C15 C16 1.22(18) .
C13 N14 C15 C18 -178.16(12) .
C12 N11 C16 C15 0.2(2) .
N14 C15 C16 N11 -1.5(2) .
C18 C15 C16 N11 177.89(13) .
C23 N21 C22 C23 -0.1(2) 2_585
C23 N21 C22 C24 179.82(12) .
C22 N21 C23 C22 0.1(2) 2_585
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139201632
