#------------------------------------------------------------------------------
#$Date: 2020-06-06 01:23:54 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022136.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_2022136
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 -, C H4 N2 O'
_chemical_formula_moiety         'C6 H9 N2 O +, I -, C H4 N2 O'
_chemical_formula_sum            'C7 H13 I N4 O2'
_chemical_formula_weight         312.11
_chemical_name_common
;
4,6-Dimethyl-2-pyrimidonium iodide--urea (1/1)
;
_chemical_name_systematic
;
4,6-Dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium iodide--urea (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_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                 127.378(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7720(10)
_cell_length_b                   11.5579(10)
_cell_length_c                   14.0700(16)
_cell_measurement_reflns_used    3188
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.43
_cell_measurement_theta_min      2.95
_cell_volume                     1133.6(2)
_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 0.994
_diffrn_measured_fraction_theta_max 0.996
_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  0.0496
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16324
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         3.413
_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    2.81
_exptl_absorpt_correction_T_max  0.5786
_exptl_absorpt_correction_T_min  0.2583
_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    1.829
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.493
_exptl_crystal_size_mid          0.421
_exptl_crystal_size_min          0.192
_refine_diff_density_max         0.843
_refine_diff_density_min         -1.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0324
_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)+(0.0610P)²+0.6546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                2800
_reflns_number_total             2995
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wp3004sup1.cif
_cod_data_source_block           5
_cod_database_code               2022136
_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   0.338
_shelx_estimated_absorpt_t_max   0.615
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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 0.83377(2) 0.74469(2) 0.35562(2) 0.02789(9) Uani d 1 . .
O O1U 0.5613(2) 0.14468(14) 0.46992(15) 0.0333(3) Uani d 1 . .
O O1 0.6489(3) 0.44215(14) 0.44055(16) 0.0342(4) Uani d 1 . .
N N2 0.7967(3) 0.44561(16) 0.35149(17) 0.0288(4) Uani d 1 . .
H H2 0.809381 0.521263 0.359539 0.035 Uiso calc 1 . .
N N6 0.6879(3) 0.27280(16) 0.37324(18) 0.0269(4) Uani d 1 . .
H H6 0.627973 0.233371 0.395104 0.032 Uiso calc 1 . .
N N1U 0.4346(3) 0.29408(18) 0.5062(2) 0.0337(4) Uani d 1 . .
H H1UA 0.485102 0.345600 0.486678 0.040 Uiso calc 1 . .
H H1UB 0.365183 0.316836 0.528741 0.040 Uiso calc 1 . .
C C1 0.7072(3) 0.39069(18) 0.39252(19) 0.0274(4) Uani d 1 . .
C C5 0.7551(3) 0.21480(19) 0.32306(19) 0.0279(4) Uani d 1 . .
C C3 0.8663(3) 0.39169(18) 0.29974(19) 0.0281(4) Uani d 1 . .
C C1U 0.4631(4) 0.1814(2) 0.5016(2) 0.0303(5) Uani d 1 . .
N N2U 0.3831(3) 0.10581(18) 0.5326(2) 0.0411(5) Uani d 1 . .
H H2UA 0.399411 0.030962 0.530629 0.049 Uiso calc 1 . .
H H2UB 0.314446 0.131331 0.554735 0.049 Uiso calc 1 . .
C C4 0.8454(4) 0.2744(2) 0.2849(2) 0.0297(4) Uani d 1 . .
H H4 0.892487 0.234216 0.248637 0.036 Uiso calc 1 . .
C C8 0.7286(4) 0.08672(19) 0.3136(2) 0.0347(5) Uani d 1 . .
H H8A 0.844970 0.049635 0.382072 0.052 Uiso calc 1 . .
H H8B 0.703908 0.059710 0.239327 0.052 Uiso calc 1 . .
H H8C 0.619515 0.066691 0.313008 0.052 Uiso calc 1 . .
C C7 0.9637(4) 0.4651(2) 0.2641(2) 0.0354(5) Uani d 1 . .
H H7A 0.877315 0.527494 0.211581 0.053 Uiso calc 1 . .
H H7B 0.997284 0.417626 0.221505 0.053 Uiso calc 1 . .
H H7C 1.080603 0.498420 0.335673 0.053 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
C1 N2 H2 . . 117.6 ?
C3 N2 H2 . . 117.6 ?
C3 N2 C1 . . 124.78(19) ?
C1 N6 H6 . . 118.1 ?
C5 N6 H6 . . 118.1 ?
C5 N6 C1 . . 123.8(2) ?
H1UA N1U H1UB . . 120.0 ?
C1U N1U H1UA . . 120.0 ?
C1U N1U H1UB . . 120.0 ?
O1 C1 N2 . . 122.90(19) ?
O1 C1 N6 . . 123.1(2) ?
N2 C1 N6 . . 113.95(18) ?
N6 C5 C4 . . 119.6(2) ?
N6 C5 C8 . . 116.7(2) ?
C4 C5 C8 . . 123.7(2) ?
N2 C3 C4 . . 118.4(2) ?
N2 C3 C7 . . 117.21(19) ?
C4 C3 C7 . . 124.4(2) ?
O1U C1U N1U . . 122.3(2) ?
O1U C1U N2U . . 119.9(2) ?
N1U C1U N2U . . 117.8(2) ?
C1U N2U H2UA . . 120.0 ?
C1U N2U H2UB . . 120.0 ?
H2UA N2U H2UB . . 120.0 ?
C5 C4 H4 . . 120.3 ?
C3 C4 C5 . . 119.4(2) ?
C3 C4 H4 . . 120.3 ?
C5 C8 H8A . . 109.5 ?
C5 C8 H8B . . 109.5 ?
C5 C8 H8C . . 109.5 ?
H8A C8 H8B . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
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 ?
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
O1U C1U . 1.260(3) ?
O1 C1 . 1.221(3) ?
N2 H2 . 0.8800 ?
N2 C1 . 1.379(3) ?
N2 C3 . 1.353(3) ?
N6 H6 . 0.8800 ?
N6 C1 . 1.379(3) ?
N6 C5 . 1.342(3) ?
N1U H1UA . 0.8800 ?
N1U H1UB . 0.8800 ?
N1U C1U . 1.336(3) ?
C5 C4 . 1.381(3) ?
C5 C8 . 1.492(3) ?
C3 C4 . 1.367(3) ?
C3 C7 . 1.491(3) ?
C1U N2U . 1.348(3) ?
N2U H2UA . 0.8800 ?
N2U H2UB . 0.8800 ?
C4 H4 . 0.9500 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
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 2.59 3.4692(19) 172.7 yes
N6 H6 O1U . 0.88 1.80 2.666(3) 166.6 yes
N1U H1UA O1 . 0.88 2.21 3.070(3) 167.4 yes
N1U H1UB I1 3_666 0.88 3.11 3.883(2) 148.4 yes
N2U H2UA O1U 3_656 0.88 2.06 2.940(3) 178.6 yes
N2U H2UB I1 3_666 0.88 2.71 3.565(2) 165.5 yes

_cod_database_fobs_code 2022136
