#------------------------------------------------------------------------------
#$Date: 2020-06-06 01:23:54 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022133.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_2022133
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 O +, H F2 -'
_chemical_formula_moiety         'C6 H9 N2 O +, F2 H -'
_chemical_formula_sum            'C6 H10 F2 N2 O'
_chemical_formula_weight         164.16
_chemical_name_systematic
;
4,6-Dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium bifluoride
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_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                 113.551(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9253(16)
_cell_length_b                   5.9962(14)
_cell_length_c                   8.433(2)
_cell_measurement_reflns_used    1096
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.44
_cell_measurement_theta_min      3.03
_cell_volume                     367.37(15)
_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 0.989
_diffrn_measured_fraction_theta_max 0.986
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6035
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.275
_diffrn_reflns_theta_min         4.301
_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    0.136
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9491
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
[X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.318
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1075
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0352
_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)+(0.0471P)²+0.1674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                1009
_reflns_number_total             1075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wp3004sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        367.39(16)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2022133
_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   0.967
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
O O1 0.71017(14) 0.250000 0.91063(13) 0.0205(2) Uani d 1 . .
N N2 0.72246(15) 0.250000 0.64423(14) 0.0140(2) Uani d 1 . .
H H2 0.601583 0.250000 0.592192 0.017 Uiso calc 1 . .
N N6 0.99054(14) 0.250000 0.89619(14) 0.0137(2) Uani d 1 . .
H H6 1.046662 0.250000 1.009730 0.016 Uiso calc 1 . .
C C1 0.80061(17) 0.250000 0.82331(16) 0.0140(3) Uani d 1 . .
C C3 0.81877(18) 0.250000 0.54510(16) 0.0142(3) Uani d 1 . .
C C4 1.00892(18) 0.250000 0.62426(16) 0.0155(3) Uani d 1 . .
H H4 1.080338 0.250000 0.556716 0.019 Uiso calc 1 . .
C C5 1.09434(17) 0.250000 0.80387(17) 0.0142(3) Uani d 1 . .
C C7 0.7107(2) 0.250000 0.35340(17) 0.0196(3) Uani d 1 . .
C C8 1.29731(18) 0.250000 0.90421(19) 0.0192(3) Uani d 1 . .
F F1 0.36129(11) 0.250000 0.50873(11) 0.0214(2) Uani d 1 . .
H H1 0.255(2) 0.250000 0.3699(12) 0.064(9) Uiso d 1 . .
F F2 0.13833(15) 0.250000 0.23660(11) 0.0316(3) Uani d 1 . .
H H7A 0.790(3) 0.250000 0.294(3) 0.030(5) Uiso d 1 . .
H H8A 1.362(3) 0.250000 0.827(3) 0.032(6) Uiso d 1 . .
H H8B 1.331(2) 0.120(3) 0.9768(18) 0.031(4) Uiso d 1 . .
H H7B 0.631(2) 0.121(3) 0.3222(19) 0.033(4) 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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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 . . 117.9 ?
C3 N2 H2 . . 117.9 ?
C3 N2 C1 . . 124.28(11) ?
C1 N6 H6 . . 118.1 ?
C5 N6 H6 . . 118.1 ?
C5 N6 C1 . . 123.71(11) ?
O1 C1 N2 . . 123.07(12) ?
O1 C1 N6 . . 122.18(12) ?
N6 C1 N2 . . 114.75(11) ?
N2 C3 C4 . . 118.80(12) ?
N2 C3 C7 . . 116.86(12) ?
C4 C3 C7 . . 124.34(12) ?
C3 C4 H4 . . 120.4 ?
C3 C4 C5 . . 119.22(12) ?
C5 C4 H4 . . 120.4 ?
N6 C5 C4 . . 119.24(12) ?
N6 C5 C8 . . 116.40(12) ?
C4 C5 C8 . . 124.36(12) ?
C3 C7 H7A . . 111.2(13) ?
C3 C7 H7B . . 108.9(9) ?
C3 C7 H7B . 4_565 108.9(9) ?
H7A C7 H7B . . 110.5(11) ?
H7A C7 H7B . 4_565 110.5(11) ?
H7B C7 H7B . 4_565 106.7(18) ?
C5 C8 H8A . . 111.1(13) ?
C5 C8 H8B . 4_565 109.1(9) ?
C5 C8 H8B . . 109.1(9) ?
H8A C8 H8B . 4_565 109.5(11) ?
H8A C8 H8B . . 109.5(11) ?
H8B C8 H8B . 4_565 108.5(17) ?
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
O1 C1 . 1.2156(16) ?
N2 H2 . 0.8800 ?
N2 C1 . 1.3846(16) ?
N2 C3 . 1.3385(16) ?
N6 H6 . 0.8800 ?
N6 C1 . 1.3800(16) ?
N6 C5 . 1.3396(16) ?
C3 C4 . 1.3831(18) ?
C3 C7 . 1.4968(18) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.3904(18) ?
C5 C8 . 1.4886(18) ?
C7 H7A . 0.95(2) ?
C7 H7B . 0.967(16) ?
C7 H7B 4_565 0.967(16) ?
C8 H8A . 0.98(2) ?
C8 H8B . 0.962(16) ?
C8 H8B 4_565 0.962(16) ?
F1 H1 . 1.1360(15) ?
F2 H1 . 1.1360(15) ?
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 F1 . 0.88 1.75 2.6240(15) 174.5 yes

_cod_database_fobs_code 2022133
