#------------------------------------------------------------------------------
#$Date: 2020-04-01 07:26:30 +0200 (Wed 01 de Apr de 2020) $
#$Revision: 249908 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/19/2021999.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_2021999
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-(3-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                 106.887(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4670(6)
_cell_length_b                   10.3070(7)
_cell_length_c                   16.6150(9)
_cell_measurement_reflns_used    6409
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1551.32(17)
_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
;
SIR2014 (Burla et al.,  2015) and SHELXS97 (Sheldrick,
2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0646
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11675
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.988
_exptl_absorpt_coefficient_mu    2.423
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(DENZO-SMN; Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.872
_refine_diff_density_min         -0.665
_refine_ls_extinction_coef       0.0024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_gt    15.23
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0498
_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)+(0.0216P)²+3.2907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                2778
_reflns_number_total             3562
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qs3091sup1.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2021999
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 0.1813(4) 0.5822(3) 0.5281(2) 0.0223(7) Uani d 1 . .
N N3 0.1369(3) 0.6656(3) 0.46276(18) 0.0244(6) Uani d 1 . .
C C4 0.1464(4) 0.6313(4) 0.3872(2) 0.0260(7) Uani d 1 . .
C C5 0.2033(4) 0.5115(3) 0.3723(2) 0.0237(7) Uani d 1 . .
H H5 0.205001 0.488716 0.318403 0.028 Uiso calc 1 . .
C C6 0.2561(4) 0.4289(3) 0.4381(2) 0.0212(7) Uani d 1 . .
N N1 0.2475(3) 0.4652(3) 0.51637(17) 0.0210(6) Uani d 1 . .
C C19 0.0951(5) 0.7282(4) 0.3183(2) 0.0388(10) Uani d 1 . .
H H19A -0.009262 0.741422 0.306893 0.058 Uiso calc 1 . .
H H19B 0.115694 0.696748 0.268472 0.058 Uiso calc 1 . .
H H19C 0.145761 0.808907 0.335035 0.058 Uiso calc 1 . .
C C13 0.3230(4) 0.3019(3) 0.4265(2) 0.0227(7) Uani d 1 . .
C C14 0.2362(5) 0.2122(4) 0.3720(2) 0.0316(8) Uani d 1 . .
H H14 0.136785 0.229841 0.346736 0.038 Uiso calc 1 . .
C C15 0.2959(5) 0.0967(4) 0.3550(3) 0.0397(10) Uani d 1 . .
H H15 0.236877 0.036854 0.318355 0.048 Uiso calc 1 . .
C C16 0.4446(5) 0.0702(4) 0.3928(3) 0.0378(10) Uani d 1 . .
H H16 0.485068 -0.007745 0.38196 0.045 Uiso calc 1 . .
C C17 0.5319(5) 0.1601(4) 0.4466(2) 0.0342(9) Uani d 1 . .
H H17 0.631556 0.142863 0.471193 0.041 Uiso calc 1 . .
C C18 0.4722(4) 0.2754(4) 0.4641(2) 0.0278(8) Uani d 1 . .
H H18 0.531297 0.335073 0.500786 0.033 Uiso calc 1 . .
C C7 0.3074(4) 0.3784(3) 0.5877(2) 0.0241(7) Uani d 1 . .
C C8 0.2319(4) 0.2664(3) 0.5924(2) 0.0251(7) Uani d 1 . .
H H8 0.141241 0.248609 0.553637 0.03 Uiso calc 1 . .
C C9 0.2965(4) 0.1796(3) 0.6580(2) 0.0275(8) Uani d 1 . .
C C10 0.4311(4) 0.2092(3) 0.7155(2) 0.0303(8) Uani d 1 . .
H H10 0.473019 0.151385 0.758826 0.036 Uiso calc 1 . .
C C11 0.5036(4) 0.3229(4) 0.7093(2) 0.0293(8) Uani d 1 . .
H H11 0.593516 0.341646 0.748582 0.035 Uiso calc 1 . .
C C12 0.4421(4) 0.4100(3) 0.6443(2) 0.0251(8) Uani d 1 . .
H H12 0.49016 0.486834 0.639024 0.03 Uiso calc 1 . .
O O1 0.2341(3) 0.0635(3) 0.66904(17) 0.0352(6) Uani d 1 . .
C C20 0.1217(5) 0.0147(4) 0.5977(3) 0.0385(10) Uani d 1 . .
H H20A 0.034797 0.067495 0.588149 0.058 Uiso calc 1 . .
H H20B 0.098418 -0.073087 0.608365 0.058 Uiso calc 1 . .
H H20C 0.156591 0.017174 0.548991 0.058 Uiso calc 1 . .
Se Se1 0.15424(5) 0.62264(4) 0.62984(2) 0.02975(13) 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
0 0 -1 0.025
0 0 1 0.015
-1 0 0 0.135
1 0 0 0.12
0 -1 0 0.095
0 1 0 0.025
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 . . 118.9(3) ?
N3 C2 Se1 . . 120.2(2) ?
N1 C2 Se1 . . 120.9(2) ?
C4 N3 C2 . . 119.9(3) ?
N3 C4 C5 . . 122.5(3) ?
N3 C4 C19 . . 116.8(3) ?
C5 C4 C19 . . 120.8(3) ?
C6 C5 C4 . . 118.7(3) ?
C6 C5 H5 . . 120.6 ?
C4 C5 H5 . . 120.6 ?
C5 C6 N1 . . 118.7(3) ?
C5 C6 C13 . . 121.1(3) ?
N1 C6 C13 . . 120.3(3) ?
C6 N1 C2 . . 121.2(3) ?
C6 N1 C7 . . 118.9(3) ?
C2 N1 C7 . . 119.9(3) ?
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 ?
C14 C13 C18 . . 119.6(3) ?
C14 C13 C6 . . 118.5(3) ?
C18 C13 C6 . . 121.8(3) ?
C15 C14 C13 . . 120.5(4) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C14 C15 C16 . . 119.8(4) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C17 C16 C15 . . 119.8(4) ?
C17 C16 H16 . . 120.1 ?
C15 C16 H16 . . 120.1 ?
C16 C17 C18 . . 120.5(4) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C17 C18 C13 . . 119.7(4) ?
C17 C18 H18 . . 120.1 ?
C13 C18 H18 . . 120.1 ?
C8 C7 C12 . . 123.5(3) ?
C8 C7 N1 . . 118.4(3) ?
C12 C7 N1 . . 118.0(3) ?
C7 C8 C9 . . 117.6(3) ?
C7 C8 H8 . . 121.2 ?
C9 C8 H8 . . 121.2 ?
O1 C9 C10 . . 116.5(3) ?
O1 C9 C8 . . 123.5(3) ?
C10 C9 C8 . . 120.0(3) ?
C11 C10 C9 . . 121.0(3) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 120.0(4) ?
C10 C11 H11 . . 120 ?
C12 C11 H11 . . 120 ?
C7 C12 C11 . . 117.9(3) ?
C7 C12 H12 . . 121 ?
C11 C12 H12 . . 121 ?
C9 O1 C20 . . 116.1(3) ?
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 ?
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 . 1.353(4) ?
C2 N1 . 1.399(4) ?
C2 Se1 . 1.829(3) ?
N3 C4 . 1.332(4) ?
C4 C5 . 1.398(5) ?
C4 C19 . 1.491(5) ?
C5 C6 . 1.361(5) ?
C5 H5 . 0.93 ?
C6 N1 . 1.379(4) ?
C6 C13 . 1.492(5) ?
N1 C7 . 1.462(4) ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C13 C14 . 1.384(5) ?
C13 C18 . 1.395(5) ?
C14 C15 . 1.382(5) ?
C14 H14 . 0.93 ?
C15 C16 . 1.392(6) ?
C15 H15 . 0.93 ?
C16 C17 . 1.382(6) ?
C16 H16 . 0.93 ?
C17 C18 . 1.382(5) ?
C17 H17 . 0.93 ?
C18 H18 . 0.93 ?
C7 C8 . 1.372(5) ?
C7 C12 . 1.385(5) ?
C8 C9 . 1.405(5) ?
C8 H8 . 0.93 ?
C9 O1 . 1.371(4) ?
C9 C10 . 1.386(5) ?
C10 C11 . 1.377(5) ?
C10 H10 . 0.93 ?
C11 C12 . 1.396(5) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
O1 C20 . 1.434(5) ?
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
C5 H5 O1 4_565 0.93 2.63 3.557(4) 174.5 yes
C8 H8 N3 3_566 0.93 2.72 3.415(5) 132.7 yes
C19 H19B Se1 4_575 0.96 3.06 3.674(4) 122.7 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
N1 C2 N3 C4 . . . . 5.1(5) ?
Se1 C2 N3 C4 . . . . -174.8(3) ?
C2 N3 C4 C5 . . . . -1.0(5) ?
C2 N3 C4 C19 . . . . 179.9(3) ?
N3 C4 C5 C6 . . . . -2.6(5) ?
C19 C4 C5 C6 . . . . 176.5(4) ?
C4 C5 C6 N1 . . . . 1.8(5) ?
C4 C5 C6 C13 . . . . -177.8(3) ?
C5 C6 N1 C2 . . . . 2.3(5) ?
C13 C6 N1 C2 . . . . -178.1(3) ?
C5 C6 N1 C7 . . . . -178.4(3) ?
C13 C6 N1 C7 . . . . 1.1(5) ?
N3 C2 N1 C6 . . . . -5.8(5) ?
Se1 C2 N1 C6 . . . . 174.1(2) ?
N3 C2 N1 C7 . . . . 174.9(3) ?
Se1 C2 N1 C7 . . . . -5.2(4) ?
C5 C6 C13 C14 . . . . -61.2(4) ?
N1 C6 C13 C14 . . . . 119.2(4) ?
C5 C6 C13 C18 . . . . 114.2(4) ?
N1 C6 C13 C18 . . . . -65.4(4) ?
C18 C13 C14 C15 . . . . 0.2(5) ?
C6 C13 C14 C15 . . . . 175.7(3) ?
C13 C14 C15 C16 . . . . 0.0(6) ?
C14 C15 C16 C17 . . . . -0.6(6) ?
C15 C16 C17 C18 . . . . 0.9(6) ?
C16 C17 C18 C13 . . . . -0.7(5) ?
C14 C13 C18 C17 . . . . 0.1(5) ?
C6 C13 C18 C17 . . . . -175.2(3) ?
C6 N1 C7 C8 . . . . -72.6(4) ?
C2 N1 C7 C8 . . . . 106.7(4) ?
C6 N1 C7 C12 . . . . 103.6(4) ?
C2 N1 C7 C12 . . . . -77.2(4) ?
C12 C7 C8 C9 . . . . -0.5(5) ?
N1 C7 C8 C9 . . . . 175.4(3) ?
C7 C8 C9 O1 . . . . -178.9(3) ?
C7 C8 C9 C10 . . . . 0.7(5) ?
O1 C9 C10 C11 . . . . 179.3(3) ?
C8 C9 C10 C11 . . . . -0.2(5) ?
C9 C10 C11 C12 . . . . -0.4(5) ?
C8 C7 C12 C11 . . . . -0.1(5) ?
N1 C7 C12 C11 . . . . -176.0(3) ?
C10 C11 C12 C7 . . . . 0.5(5) ?
C10 C9 O1 C20 . . . . -161.7(3) ?
C8 C9 O1 C20 . . . . 17.8(5) ?

_cod_database_fobs_code 2021999
