#------------------------------------------------------------------------------
#$Date: 2020-09-30 07:43:55 +0300 (Wed, 30 Sep 2020) $
#$Revision: 256848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022259.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_2022259
loop_
_publ_author_name
'Grześkiewicz, Anita M.'
'Ostrowska, Agata'
'Borzylo, Dmytro'
'Kubicki, Maciej'
_publ_section_title
;
 When solvent becomes reactant: a study of 6-aminothiocytosine derivatives
;
_journal_coeditor_code           ZO3006
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              992
_journal_page_last               999
_journal_paper_doi               10.1107/S2053229620012504
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C9 H12 N8 S2'
_chemical_formula_moiety         'C9 H12 N8 S2'
_chemical_formula_sum            'C9 H12 N8 S2'
_chemical_formula_weight         296.39
_chemical_name_systematic
;
2,2'-[Methanediylbis(sulfanediyl)]bis(pyrimidine-4,6-diamine)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.9868(10)
_cell_length_b                   15.5842(4)
_cell_length_c                   4.21310(10)
_cell_measurement_reflns_used    3186
_cell_measurement_temperature    130.0(10)
_cell_measurement_theta_max      75.1210
_cell_measurement_theta_min      4.7750
_cell_volume                     2428.47(11)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      130.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku SuperNova Single Source diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4267
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         75.798
_diffrn_reflns_theta_min         4.782
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.159
_refine_ls_abs_structure_details
;
Flack x determined using 436 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.001(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1171
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0228
_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)+(0.0386P)²+2.5037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0622
_reflns_number_gt                1153
_reflns_number_total             1171
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zo3006sup1.cif
_cod_data_source_block           2
_cod_database_code               2022259
_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'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.33494(5) 0.31726(11) 0.3752(5) 0.0233(4) Uani d 1 . .
C C2 0.30593(6) 0.32157(14) 0.5623(6) 0.0224(5) Uani d 1 . .
N N3 0.28855(5) 0.38998(11) 0.6691(7) 0.0244(4) Uani d 1 . .
C C4 0.30253(6) 0.46631(13) 0.5759(6) 0.0243(5) Uani d 1 . .
N N4 0.28395(6) 0.53599(11) 0.6790(8) 0.0319(4) Uani d 1 . .
H H4A 0.2922 0.5857 0.6680 0.038 Uiso d 1 . .
H H4B 0.2696 0.5212 0.8300 0.038 Uiso d 1 . .
C C5 0.33268(6) 0.47186(13) 0.3806(6) 0.0250(5) Uani d 1 . .
H H5 0.3422 0.5257 0.3158 0.030 Uiso calc 1 . .
C C6 0.34835(6) 0.39450(14) 0.2836(6) 0.0238(4) Uani d 1 . .
N N6 0.37774(5) 0.39304(13) 0.0935(5) 0.0290(5) Uani d 1 . .
H H6A 0.3872 0.3437 0.0353 0.035 Uiso calc 1 . .
H H6B 0.3874 0.4415 0.0278 0.035 Uiso calc 1 . .
S S7 0.28927(2) 0.21932(3) 0.67621(18) 0.02388(16) Uani d 1 . .
C C8 0.2500 0.2500 0.9038(9) 0.0241(6) Uani d 1 . .
H H8A 0.2434 0.2024 1.0400 0.029 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 0.0181 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 . . 114.67(19) ?
N3 C2 N1 . . 129.2(2) ?
N3 C2 S7 . . 117.56(17) ?
N1 C2 S7 . . 113.21(16) ?
C2 N3 C4 . . 115.0(2) ?
N3 C4 N4 . . 114.6(2) ?
N3 C4 C5 . . 122.2(2) ?
N4 C4 C5 . . 123.1(2) ?
C4 N4 H4A . . 122.8 ?
C4 N4 H4B . . 109.6 ?
H4A N4 H4B . . 121.0 ?
C4 C5 C6 . . 116.9(2) ?
C4 C5 H5 . . 121.6 ?
C6 C5 H5 . . 121.6 ?
N6 C6 N1 . . 116.6(2) ?
N6 C6 C5 . . 121.4(2) ?
N1 C6 C5 . . 122.0(2) ?
C6 N6 H6A . . 120.0 ?
C6 N6 H6B . . 120.0 ?
H6A N6 H6B . . 120.0 ?
C2 S7 C8 . . 100.67(8) ?
S7 C8 S7 14 . 115.8(2) ?
S7 C8 H8A 14 . 108.3 ?
S7 C8 H8A . . 108.3 ?
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
N1 C2 . 1.333(3) ?
N1 C6 . 1.358(3) ?
C2 N3 . 1.324(3) ?
C2 S7 . 1.775(2) ?
N3 C4 . 1.355(3) ?
C4 N4 . 1.356(3) ?
C4 C5 . 1.389(4) ?
N4 H4A . 0.8337 ?
N4 H4B . 0.8606 ?
C5 C6 . 1.398(3) ?
C5 H5 . 0.9500 ?
C6 N6 . 1.351(3) ?
N6 H6A . 0.8800 ?
N6 H6B . 0.8800 ?
S7 C8 . 1.805(2) ?
C8 S7 14 1.805(2) ?
C8 H8A . 0.9700 ?
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
C6 N1 C2 N3 . . . . 0.2(4) ?
C6 N1 C2 S7 . . . . 179.97(16) ?
N1 C2 N3 C4 . . . . -0.5(4) ?
S7 C2 N3 C4 . . . . 179.73(18) ?
C2 N3 C4 N4 . . . . 178.2(3) ?
C2 N3 C4 C5 . . . . 0.5(4) ?
N3 C4 C5 C6 . . . . -0.3(4) ?
N4 C4 C5 C6 . . . . -177.8(3) ?
C2 N1 C6 N6 . . . . -179.9(2) ?
C2 N1 C6 C5 . . . . 0.1(3) ?
C4 C5 C6 N6 . . . . 180.0(2) ?
C4 C5 C6 N1 . . . . -0.1(4) ?
N3 C2 S7 C8 . . . . 2.5(2) ?
N1 C2 S7 C8 . . . . -177.34(18) ?
C2 S7 C8 S7 . . . 14 78.08(8) ?

_cod_database_fobs_code 2022259
