#------------------------------------------------------------------------------
#$Date: 2020-04-01 08:26:30 +0300 (Wed, 01 Apr 2020) $
#$Revision: 249908 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/20/2022000.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_2022000
loop_
_publ_author_name
'Żesławska, Ewa'
'Korona-Głowniak, Izabela'
'Nitek, Wojciech'
'Tejchman, Waldemar'
_publ_section_title
;
 Effect of the position of a methoxy substituent on the antimicrobial
 activity and crystal structures of
 4-methyl-1,6-diphenylpyrimidine-2(1H)-selenone derivatives
;
_journal_coeditor_code           QS3091
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              359
_journal_page_last               366
_journal_paper_doi               10.1107/S2053229620004040
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C18 H16 N2 O Se'
_chemical_formula_moiety         'C18 H16 N2 O Se'
_chemical_formula_sum            'C18 H16 N2 O Se'
_chemical_formula_weight         355.29
_chemical_name_systematic
;
4-Methyl-1-(4-methoxyphenyl)-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                 101.862(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7330(3)
_cell_length_b                   8.9500(2)
_cell_length_c                   14.1399(5)
_cell_measurement_reflns_used    18676
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1576.98(8)
_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
;
ORTEP-3 (Farrugia, 2012) and 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 0.979
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker 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  0.1041
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.723
_diffrn_reflns_theta_min         3.005
_exptl_absorpt_coefficient_mu    2.384
_exptl_absorpt_correction_T_max  1.1865
_exptl_absorpt_correction_T_min  0.8676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(DENZO-SMN; Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.99
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.942
_refine_diff_density_min         -0.818
_refine_ls_extinction_coef       0.0249(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_gt    12.971
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0604P)²+1.1117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                3229
_reflns_number_total             3626
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qs3091sup1.cif
_cod_data_source_block           3
_cod_original_cell_volume        1576.98(7)
_cod_original_sg_symbol_Hall     '-P 2yn'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022000
_shelx_estimated_absorpt_t_min   0.223
_shelx_estimated_absorpt_t_max   0.832
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
N N1 0.52843(15) 0.7407(2) 0.43405(13) 0.0123(4) Uani d 1 . .
C C2 0.46185(19) 0.6927(2) 0.49498(17) 0.0117(4) Uani d 1 . .
N N3 0.36047(15) 0.6493(2) 0.45589(14) 0.0136(4) Uani d 1 . .
C C4 0.32605(18) 0.6505(2) 0.36117(17) 0.0149(4) Uani d 1 . .
C C5 0.39026(19) 0.6995(2) 0.29741(17) 0.0149(5) Uani d 1 . .
H H5 0.362934 0.702177 0.229651 0.018 Uiso calc 1 . .
C C6 0.49275(18) 0.7429(2) 0.33549(16) 0.0136(4) Uani d 1 . .
C C7 0.63567(19) 0.7957(2) 0.47412(16) 0.0125(4) Uani d 1 . .
C C8 0.72006(19) 0.6957(2) 0.49859(16) 0.0132(4) Uani d 1 . .
H H8 0.707767 0.59125 0.491031 0.016 Uiso calc 1 . .
C C9 0.82185(18) 0.7494(3) 0.53396(16) 0.0154(4) Uani d 1 . .
H H9 0.880382 0.681985 0.55034 0.018 Uiso calc 1 . .
C C10 0.83927(18) 0.9039(2) 0.54585(16) 0.0148(4) Uani d 1 . .
C C11 0.75435(19) 1.0028(2) 0.52104(17) 0.0166(4) Uani d 1 . .
H H11 0.765976 1.107268 0.52918 0.02 Uiso calc 1 . .
C C12 0.65183(18) 0.9478(2) 0.48407(16) 0.0155(4) Uani d 1 . .
H H12 0.593266 1.014712 0.465773 0.019 Uiso calc 1 . .
C C13 0.56766(19) 0.7855(3) 0.27191(16) 0.0142(4) Uani d 1 . .
C C14 0.6437(2) 0.6833(3) 0.25498(19) 0.0202(5) Uani d 1 . .
H H14 0.651673 0.590285 0.288079 0.024 Uiso calc 1 . .
C C15 0.7082(2) 0.7171(3) 0.1895(2) 0.0233(5) Uani d 1 . .
H H15 0.760413 0.647327 0.178138 0.028 Uiso calc 1 . .
C C16 0.6964(2) 0.8524(3) 0.14084(18) 0.0227(5) Uani d 1 . .
H H16 0.740188 0.875011 0.095883 0.027 Uiso calc 1 . .
C C17 0.6205(2) 0.9548(3) 0.15775(19) 0.0237(5) Uani d 1 . .
H H17 0.612471 1.047513 0.124347 0.028 Uiso calc 1 . .
C C18 0.55606(19) 0.9218(3) 0.22372(18) 0.0190(5) Uani d 1 . .
H H18 0.504449 0.992138 0.235664 0.023 Uiso calc 1 . .
C C19 0.21606(19) 0.5904(3) 0.32206(18) 0.0204(5) Uani d 1 . .
H H19A 0.221102 0.484575 0.3057 0.031 Uiso calc 1 . .
H H19B 0.183076 0.646321 0.26395 0.031 Uiso calc 1 . .
H H19C 0.171978 0.600824 0.370911 0.031 Uiso calc 1 . .
C C20 0.9634(2) 1.0987(3) 0.60663(19) 0.0243(5) Uani d 1 . .
H H20A 0.943755 1.158416 0.54755 0.036 Uiso calc 1 . .
H H20B 1.039785 1.112586 0.63465 0.036 Uiso calc 1 . .
H H20C 0.920634 1.130813 0.65322 0.036 Uiso calc 1 . .
O O1 0.94287(13) 0.94392(19) 0.58392(12) 0.0197(4) Uani d 1 . .
Se Se1 0.50781(2) 0.68872(2) 0.62690(2) 0.01518(12) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0
-1 0 1 0.23
-1 0 -1 0.41
1 0 1 0.23
-1 1 1 0.3
-1 -1 1 0.28
1 -3 -1 0.24
1 3 -1 0.32
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
C6 N1 C2 . . 120.96(19) ?
C6 N1 C7 . . 118.63(18) ?
C2 N1 C7 . . 120.35(19) ?
N3 C2 N1 . . 119.1(2) ?
N3 C2 Se1 . . 119.17(16) ?
N1 C2 Se1 . . 121.73(17) ?
C4 N3 C2 . . 120.12(19) ?
N3 C4 C5 . . 122.5(2) ?
N3 C4 C19 . . 117.5(2) ?
C5 C4 C19 . . 119.9(2) ?
C6 C5 C4 . . 118.1(2) ?
C6 C5 H5 . . 120.9 ?
C4 C5 H5 . . 120.9 ?
C5 C6 N1 . . 119.1(2) ?
C5 C6 C13 . . 121.0(2) ?
N1 C6 C13 . . 119.8(2) ?
C12 C7 C8 . . 121.3(2) ?
C12 C7 N1 . . 118.9(2) ?
C8 C7 N1 . . 119.78(19) ?
C9 C8 C7 . . 119.2(2) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
C8 C9 C10 . . 120.1(2) ?
C8 C9 H9 . . 120 ?
C10 C9 H9 . . 120 ?
O1 C10 C11 . . 124.9(2) ?
O1 C10 C9 . . 114.91(19) ?
C11 C10 C9 . . 120.2(2) ?
C10 C11 C12 . . 119.5(2) ?
C10 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
C7 C12 C11 . . 119.7(2) ?
C7 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C14 C13 C18 . . 120.1(2) ?
C14 C13 C6 . . 119.4(2) ?
C18 C13 C6 . . 120.3(2) ?
C13 C14 C15 . . 119.9(2) ?
C13 C14 H14 . . 120 ?
C15 C14 H14 . . 120 ?
C16 C15 C14 . . 120.1(2) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 120.0(2) ?
C15 C16 H16 . . 120 ?
C17 C16 H16 . . 120 ?
C16 C17 C18 . . 120.1(2) ?
C16 C17 H17 . . 120 ?
C18 C17 H17 . . 120 ?
C13 C18 C17 . . 119.7(2) ?
C13 C18 H18 . . 120.1 ?
C17 C18 H18 . . 120.1 ?
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 ?
O1 C20 H20A . . 109.5 ?
O1 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O1 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C10 O1 C20 . . 117.29(18) ?
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
N1 C6 . 1.374(3) ?
N1 C2 . 1.395(3) ?
N1 C7 . 1.452(3) ?
C2 N3 . 1.353(3) ?
C2 Se1 . 1.837(2) ?
N3 C4 . 1.321(3) ?
C4 C5 . 1.406(3) ?
C4 C19 . 1.496(3) ?
C5 C6 . 1.362(3) ?
C5 H5 . 0.95 ?
C6 C13 . 1.489(3) ?
C7 C12 . 1.380(3) ?
C7 C8 . 1.387(3) ?
C8 C9 . 1.377(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.405(3) ?
C9 H9 . 0.95 ?
C10 O1 . 1.366(3) ?
C10 C11 . 1.386(3) ?
C11 C12 . 1.393(3) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 C14 . 1.388(3) ?
C13 C18 . 1.390(3) ?
C14 C15 . 1.391(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.385(4) ?
C15 H15 . 0.95 ?
C16 C17 . 1.387(4) ?
C16 H16 . 0.95 ?
C17 C18 . 1.395(3) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 O1 . 1.434(3) ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
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
C8 H8 N3 3_666 0.95 2.49 3.357(3) 151 yes
C11 H11 N3 3_676 0.95 2.74 3.484(3) 135.4 yes
C12 H12 Se1 3_676 0.95 3.12 3.983(2) 152.1 yes
C16 H16 N3 4_675 0.95 2.75 3.668(3) 162.9 yes
C19 H19B Se1 4_575 0.98 3.02 3.943(2) 156.9 yes
C20 H20C Se1 2_656 0.98 3.1 3.796(3) 129.4 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 N3 . . . . -0.7(3) ?
C7 N1 C2 N3 . . . . 176.62(18) ?
C6 N1 C2 Se1 . . . . 179.97(15) ?
C7 N1 C2 Se1 . . . . -2.7(3) ?
N1 C2 N3 C4 . . . . 1.0(3) ?
Se1 C2 N3 C4 . . . . -179.63(16) ?
C2 N3 C4 C5 . . . . -1.7(3) ?
C2 N3 C4 C19 . . . . 175.46(19) ?
N3 C4 C5 C6 . . . . 1.9(3) ?
C19 C4 C5 C6 . . . . -175.1(2) ?
C4 C5 C6 N1 . . . . -1.5(3) ?
C4 C5 C6 C13 . . . . 175.6(2) ?
C2 N1 C6 C5 . . . . 1.0(3) ?
C7 N1 C6 C5 . . . . -176.35(19) ?
C2 N1 C6 C13 . . . . -176.16(19) ?
C7 N1 C6 C13 . . . . 6.5(3) ?
C6 N1 C7 C12 . . . . 80.2(3) ?
C2 N1 C7 C12 . . . . -97.1(2) ?
C6 N1 C7 C8 . . . . -97.7(2) ?
C2 N1 C7 C8 . . . . 85.0(3) ?
C12 C7 C8 C9 . . . . 0.3(3) ?
N1 C7 C8 C9 . . . . 178.2(2) ?
C7 C8 C9 C10 . . . . 0.6(3) ?
C8 C9 C10 O1 . . . . 178.3(2) ?
C8 C9 C10 C11 . . . . -0.7(3) ?
O1 C10 C11 C12 . . . . -179.0(2) ?
C9 C10 C11 C12 . . . . -0.2(3) ?
C8 C7 C12 C11 . . . . -1.2(3) ?
N1 C7 C12 C11 . . . . -179.07(19) ?
C10 C11 C12 C7 . . . . 1.1(3) ?
C5 C6 C13 C14 . . . . -100.5(3) ?
N1 C6 C13 C14 . . . . 76.6(3) ?
C5 C6 C13 C18 . . . . 74.3(3) ?
N1 C6 C13 C18 . . . . -108.6(3) ?
C18 C13 C14 C15 . . . . -0.2(4) ?
C6 C13 C14 C15 . . . . 174.7(2) ?
C13 C14 C15 C16 . . . . -0.3(4) ?
C14 C15 C16 C17 . . . . 0.4(4) ?
C15 C16 C17 C18 . . . . 0.0(4) ?
C14 C13 C18 C17 . . . . 0.5(4) ?
C6 C13 C18 C17 . . . . -174.3(2) ?
C16 C17 C18 C13 . . . . -0.4(4) ?
C11 C10 O1 C20 . . . . 5.0(3) ?
C9 C10 O1 C20 . . . . -173.93(19) ?
