#------------------------------------------------------------------------------
#$Date: 2020-06-06 01:23:54 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022139.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_2022139
loop_
_publ_author_name
'Okuniewski, Andrzej'
'Rosiak, Damian'
'Chojnacki, Jarosław'
_publ_section_title
;
 Impact of the anion and chalcogen on the crystal structure and properties
 of 4,6-dimethyl-2-pyrimido(thio)nium halides
;
_journal_coeditor_code           WP3004
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              468
_journal_page_last               475
_journal_paper_doi               10.1107/S2053229620005525
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C6 H9 N2 S +, I -'
_chemical_formula_moiety         'C6 H9 N2 S +, I -'
_chemical_formula_sum            'C6 H9 I N2 S'
_chemical_formula_weight         268.11
_chemical_name_common            '4,6-Dimethyl-2-pyrimidothionium iodide'
_chemical_name_systematic
;
4,6-Dimethyl-2-sulfanylidene-2,3-dihydropyrimidin-1-ium iodide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           63
_space_group_name_Hall           '-C 2c 2'
_space_group_name_H-M_alt        'C m c m'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7198(14)
_cell_length_b                   15.095(3)
_cell_length_c                   7.0716(11)
_cell_measurement_reflns_used    1294
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.65
_cell_measurement_theta_min      3.89
_cell_volume                     930.8(3)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2009)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7434
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.887
_diffrn_reflns_theta_min         3.948
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.60
_exptl_absorpt_correction_T_max  0.8373
_exptl_absorpt_correction_T_min  0.5204
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
[X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.913
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.104
_refine_diff_density_min         -0.880
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     42
_refine_ls_number_reflns         708
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0599
_reflns_number_gt                661
_reflns_number_total             708
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wp3004sup1.cif
_cod_data_source_block           10
_cod_database_code               2022139
_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.
;
_shelx_estimated_absorpt_t_min   0.580
_shelx_estimated_absorpt_t_max   0.841
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'x+1/2, -y+1/2, z-1/2'
'-x+1/2, y+1/2, z'
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
I I1 0.000000 0.18528(2) 0.750000 0.02004(12) Uani d 1 . .
S S1 0.500000 0.12787(8) 0.750000 0.0258(3) Uani d 1 . .
N N2 0.3682(3) 0.28725(19) 0.750000 0.0195(6) Uani d 1 . .
H H2 0.280127 0.258795 0.750000 0.023 Uiso calc 1 . .
C C1 0.500000 0.2378(3) 0.750000 0.0198(9) Uani d 1 . .
C C4 0.500000 0.4226(3) 0.750000 0.0201(9) Uani d 1 . .
H H4 0.499999 0.485535 0.750000 0.024 Uiso calc 1 . .
C C3 0.3643(4) 0.3766(2) 0.750000 0.0201(6) Uani d 1 . .
C C7 0.2109(5) 0.4189(2) 0.750000 0.0298(8) Uani d 1 . .
H H7A 0.220(4) 0.4836(3) 0.750000 0.062(18) Uiso d 1 . .
H H7B 0.1549(12) 0.3999(11) 0.63687(7) 0.049(11) 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'
I I -0.4742 1.8119 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N2 H2 . . 117.8 ?
C3 N2 H2 . . 117.8 ?
C3 N2 C1 . . 124.5(3) ?
N2 C1 S1 3_656 . 123.0(2) ?
N2 C1 S1 . . 123.0(2) ?
N2 C1 N2 3_656 . 113.9(4) ?
C3 C4 H4 . . 120.4 ?
C3 C4 H4 3_656 . 120.4 ?
C3 C4 C3 . 3_656 119.2(4) ?
N2 C3 C4 . . 118.9(3) ?
N2 C3 C7 . . 117.0(3) ?
C4 C3 C7 . . 124.1(3) ?
C3 C7 H7A . . 111(2) ?
C3 C7 H7B . . 108.9(10) ?
C3 C7 H7B . 10_557 108.9(10) ?
H7A C7 H7B . . 109.43(13) ?
H7A C7 H7B . 10_557 109.43(13) ?
H7B C7 H7B . 10_557 109.43(16) ?
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 C1 . 1.659(5) ?
N2 H2 . 0.8800 ?
N2 C1 . 1.371(4) ?
N2 C3 . 1.350(4) ?
C4 H4 . 0.9500 ?
C4 C3 . 1.372(4) ?
C4 C3 3_656 1.372(4) ?
C3 C7 . 1.482(5) ?
C7 H7A . 0.9800(11) ?
C7 H7B . 0.9800(7) ?
C7 H7B 10_557 0.9800(7) ?
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
N2 H2 I1 . 0.88 2.68 3.561(3) 175.2 yes

_cod_database_fobs_code 2022139
