#------------------------------------------------------------------------------
#$Date: 2020-06-06 01:23:54 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022135.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_2022135
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 +, I -'
_chemical_formula_moiety         'C6 H9 N2 O +, I -'
_chemical_formula_sum            'C6 H9 I N2 O'
_chemical_formula_weight         252.05
_chemical_name_common            '4,6-Dimethyl-2-pyrimidonium iodide'
_chemical_name_systematic
;
4,6-Dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium iodide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.603(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1803(10)
_cell_length_b                   7.2139(18)
_cell_length_c                   8.6574(12)
_cell_measurement_reflns_used    1779
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      3.4
_cell_volume                     440.78(14)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0662
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5622
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.981
_diffrn_reflns_theta_min         3.394
_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    3.574
_exptl_absorpt_correction_T_max  0.6242
_exptl_absorpt_correction_T_min  0.2743
_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    1.899
_exptl_crystal_description       needles
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.657
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.142
_refine_diff_density_max         1.550
_refine_diff_density_min         -1.288
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     49
_refine_ls_number_reflns         1166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0589
_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)+(0.0966P)²+2.7212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1646
_reflns_number_gt                1143
_reflns_number_total             1166
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wp3004sup1.cif
_cod_data_source_block           4
_cod_database_code               2022135
_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   0.202
_shelx_estimated_absorpt_t_max   0.631
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'
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 0.250000 0.36113(8) 0.750000 0.0398(3) Uani d 1 . .
C C1 0.250000 0.4775(14) 0.250000 0.0394(19) Uani d 1 . .
C C3 0.2593(9) 0.7723(10) 0.3881(9) 0.0394(13) Uani d 1 . .
N N2 0.2632(9) 0.5837(9) 0.3837(7) 0.0411(12) Uani d 1 . .
H H2 0.275074 0.524688 0.473976 0.049 Uiso calc 1 . .
C C7 0.2664(18) 0.8639(11) 0.5416(12) 0.056(2) Uani d 1 . .
H H7A 0.143381 0.851002 0.574207 0.085 Uiso calc 1 . .
H H7B 0.295644 0.995667 0.532394 0.085 Uiso calc 1 . .
H H7C 0.364872 0.805749 0.620039 0.085 Uiso calc 1 . .
O O1 0.250000 0.3089(13) 0.250000 0.058(2) Uani d 1 . .
C C4 0.250000 0.8710(12) 0.250000 0.041(2) Uani d 1 . .
H H4 0.249999 1.002703 0.250000 0.049 Uiso calc 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'
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
N2 C1 N2 2 . 112.4(9) ?
O1 C1 N2 . 2 123.8(4) ?
O1 C1 N2 . . 123.8(4) ?
N2 C3 C7 . . 118.3(7) ?
N2 C3 C4 . . 119.3(7) ?
C4 C3 C7 . . 122.4(7) ?
C1 N2 H2 . . 117.3 ?
C3 N2 C1 . . 125.5(7) ?
C3 N2 H2 . . 117.3 ?
C3 C7 H7A . . 109.5 ?
C3 C7 H7B . . 109.5 ?
C3 C7 H7C . . 109.5 ?
H7A C7 H7B . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C3 C4 C3 2 . 118.0(9) ?
C3 C4 H4 . . 121.0 ?
C3 C4 H4 2 . 121.0 ?
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
C1 N2 . 1.377(8) ?
C1 N2 2 1.377(8) ?
C1 O1 . 1.216(14) ?
C3 N2 . 1.362(9) ?
C3 C7 . 1.477(12) ?
C3 C4 . 1.382(8) ?
N2 H2 . 0.8800 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C4 H4 . 0.9500 ?
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 2.70 3.571(7) 170.3 yes

_cod_database_fobs_code 2022135
