#------------------------------------------------------------------------------
#$Date: 2022-01-07 01:32:48 +0200 (Fri, 07 Jan 2022) $
#$Revision: 271917 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022464.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_2022464
loop_
_publ_author_name
'Korona-Głowniak, Izabela'
'Nitek, Wojciech'
'Tejchman, Waldemar'
'Żesławska, Ewa'
_publ_section_title
;
 Influence of chlorine and methyl substituents and their position on the
 antimicrobial activities and crystal structures of
 4-methyl-1,6-diphenylpyrimidine-2(1H)-selenone derivatives
;
_journal_coeditor_code           KY3209
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              649
_journal_page_last               658
_journal_paper_doi               10.1107/S205322962100975X
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C18 H16 N2 Se'
_chemical_formula_moiety         'C18 H16 N2 Se'
_chemical_formula_sum            'C18 H16 N2 Se'
_chemical_formula_weight         339.29
_chemical_name_systematic
;
4-Methyl-1-(3-methylphenyl)-6-phenylpyrimidine-2(1H)-selenone
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 108.025(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4770(7)
_cell_length_b                   19.6180(15)
_cell_length_c                   9.8030(9)
_cell_measurement_reflns_used    5719
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1550.2(2)
_computing_cell_refinement
;
SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Bruker, 2004)
;
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1194
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.401
_diffrn_reflns_theta_min         2.419
_exptl_absorpt_coefficient_mu    2.417
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(DENZO-SMN; Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.391
_refine_diff_density_min         -0.83
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    10.686
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.105
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0310P)²+4.9629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                2550
_reflns_number_total             3479
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ky3209sup1.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 2022463--2022466.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022464
_cod_database_fobs_code          2022464
_shelx_estimated_absorpt_t_min   0.452
_shelx_estimated_absorpt_t_max   0.812
loop_
_symmetry_equiv_pos_as_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
C C2 0.4682(5) -0.0418(2) 0.3230(5) 0.0196(10) Uani d 1 . .
N N1 0.4774(4) 0.01976(18) 0.2559(4) 0.0167(8) Uani d 1 . .
C C6 0.6255(5) 0.0417(2) 0.2389(4) 0.0174(9) Uani d 1 . .
C C5 0.7609(5) 0.0008(2) 0.2858(4) 0.0186(9) Uani d 1 . .
H H5 0.862711 0.014474 0.277746 0.022 Uiso calc 1 . .
C C4 0.7443(5) -0.0628(2) 0.3468(4) 0.0205(9) Uani d 1 . .
N N3 0.6025(5) -0.08355(18) 0.3626(4) 0.0196(8) Uani d 1 . .
C C19 0.8902(6) -0.1095(3) 0.3983(6) 0.0335(12) Uani d 1 . .
H H19A 0.853671 -0.153359 0.419657 0.05 Uiso calc 1 . .
H H19B 0.96786 -0.090829 0.483341 0.05 Uiso calc 1 . .
H H19C 0.942885 -0.114136 0.325079 0.05 Uiso calc 1 . .
C C13 0.6284(5) 0.1088(2) 0.1697(5) 0.0183(9) Uani d 1 . .
C C18 0.5588(6) 0.1169(3) 0.0227(5) 0.0236(10) Uani d 1 . .
H H18 0.510931 0.079898 -0.034525 0.028 Uiso calc 1 . .
C C17 0.5609(6) 0.1805(3) -0.0385(5) 0.0268(11) Uani d 1 . .
H H170 0.516632 0.18592 -0.13728 0.032 Uiso calc 1 . .
C C16 0.6284(6) 0.2356(2) 0.0467(5) 0.0246(11) Uani d 1 . .
H H160 0.625099 0.278559 0.005577 0.03 Uiso calc 1 . .
C C15 0.7009(5) 0.2276(2) 0.1926(5) 0.0222(10) Uani d 1 . .
H H150 0.748339 0.264773 0.249303 0.027 Uiso calc 1 . .
C C14 0.7027(5) 0.1639(2) 0.2544(5) 0.0204(10) Uani d 1 . .
H H14 0.75363 0.158021 0.352303 0.025 Uiso calc 1 . .
C C7 0.3326(6) 0.0637(3) 0.2074(5) 0.0244(10) Uani d 1 . .
C C12 0.2131(6) 0.0496(3) 0.0762(5) 0.0298(12) Uani d 1 . .
H H12 0.223664 0.012013 0.021893 0.036 Uiso calc 1 . .
C C11 0.0789(6) 0.0929(3) 0.0292(6) 0.0382(14) Uani d 1 . .
H H11 -0.002731 0.084434 -0.057523 0.046 Uiso calc 1 . .
C C10 0.0658(7) 0.1480(3) 0.1096(6) 0.0371(13) Uani d 1 . .
H H10 -0.025477 0.176652 0.076085 0.045 Uiso calc 1 . .
C C9 0.1837(6) 0.1629(3) 0.2392(6) 0.0317(12) Uani d 1 . .
C C8 0.3199(6) 0.1186(2) 0.2895(5) 0.0251(11) Uani d 1 . .
H H8 0.400099 0.12647 0.377242 0.03 Uiso calc 1 . .
C C20 0.1713(8) 0.2248(3) 0.3260(7) 0.0442(15) Uani d 1 . .
H H20A 0.188313 0.2651 0.276822 0.066 Uiso calc 1 . .
H H20B 0.254342 0.222363 0.418227 0.066 Uiso calc 1 . .
H H20C 0.063305 0.226386 0.338266 0.066 Uiso calc 1 . .
Se Se1 0.27704(6) -0.06709(2) 0.36013(5) 0.02394(16) Uani 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.045
0 0 -1 0.075
-1 0 0 0.139
1 0 0 0.255
0 -1 0 0.055
0 1 0 0.035
3 0 1 0.14
2 0 -3 0.106
1 3 0 0.13
1 -2 0 0.19
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
N3 C2 N1 . . 119.6(3) ?
N3 C2 Se1 . . 119.6(3) ?
N1 C2 Se1 . . 120.8(3) ?
C6 N1 C2 . . 120.9(4) ?
C6 N1 C7 . . 118.8(3) ?
C2 N1 C7 . . 120.3(3) ?
C5 C6 N1 . . 118.5(4) ?
C5 C6 C13 . . 123.2(4) ?
N1 C6 C13 . . 118.3(4) ?
C6 C5 C4 . . 118.8(4) ?
C6 C5 H5 . . 120.6 ?
C4 C5 H5 . . 120.6 ?
N3 C4 C5 . . 122.4(4) ?
N3 C4 C19 . . 117.3(4) ?
C5 C4 C19 . . 120.3(4) ?
C4 N3 C2 . . 119.5(4) ?
C4 C19 H19A . . 109.5 ?
C4 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C4 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C18 C13 C14 . . 120.0(4) ?
C18 C13 C6 . . 121.0(4) ?
C14 C13 C6 . . 119.1(4) ?
C17 C18 C13 . . 119.6(5) ?
C17 C18 H18 . . 120.2 ?
C13 C18 H18 . . 120.2 ?
C16 C17 C18 . . 120.2(4) ?
C16 C17 H170 . . 119.9 ?
C18 C17 H170 . . 119.9 ?
C17 C16 C15 . . 120.4(4) ?
C17 C16 H160 . . 119.8 ?
C15 C16 H160 . . 119.8 ?
C16 C15 C14 . . 119.8(4) ?
C16 C15 H150 . . 120.1 ?
C14 C15 H150 . . 120.1 ?
C15 C14 C13 . . 119.9(4) ?
C15 C14 H14 . . 120 ?
C13 C14 H14 . . 120 ?
C8 C7 C12 . . 122.0(5) ?
C8 C7 N1 . . 119.1(4) ?
C12 C7 N1 . . 118.9(4) ?
C11 C12 C7 . . 118.3(5) ?
C11 C12 H12 . . 120.8 ?
C7 C12 H12 . . 120.8 ?
C10 C11 C12 . . 120.1(5) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C11 C10 C9 . . 122.3(5) ?
C11 C10 H10 . . 118.9 ?
C9 C10 H10 . . 118.9 ?
C10 C9 C8 . . 118.2(5) ?
C10 C9 C20 . . 122.2(5) ?
C8 C9 C20 . . 119.6(5) ?
C7 C8 C9 . . 119.1(5) ?
C7 C8 H8 . . 120.4 ?
C9 C8 H8 . . 120.4 ?
C9 C20 H20A . . 109.5 ?
C9 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C9 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 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
C2 N3 . 1.358(6) ?
C2 N1 . 1.389(6) ?
C2 Se1 . 1.835(4) ?
N1 C6 . 1.386(5) ?
N1 C7 . 1.453(6) ?
C6 C5 . 1.359(6) ?
C6 C13 . 1.483(6) ?
C5 C4 . 1.409(6) ?
C5 H5 . 0.93 ?
C4 N3 . 1.322(5) ?
C4 C19 . 1.496(6) ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C13 C18 . 1.388(6) ?
C13 C14 . 1.389(6) ?
C18 C17 . 1.387(7) ?
C18 H18 . 0.93 ?
C17 C16 . 1.379(7) ?
C17 H170 . 0.93 ?
C16 C15 . 1.380(7) ?
C16 H160 . 0.93 ?
C15 C14 . 1.387(6) ?
C15 H150 . 0.93 ?
C14 H14 . 0.93 ?
C7 C8 . 1.369(7) ?
C7 C12 . 1.397(7) ?
C12 C11 . 1.379(7) ?
C12 H12 . 0.93 ?
C11 C10 . 1.363(9) ?
C11 H11 . 0.93 ?
C10 C9 . 1.383(8) ?
C10 H10 . 0.93 ?
C9 C8 . 1.407(7) ?
C9 C20 . 1.504(7) ?
C8 H8 . 0.93 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
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
C19 H19C Se1 1_655 0.96 2.90 3.513(5) 123.0 yes
C8 H8 N3 3_656 0.93 2.70 3.339(6) 127.3 yes
