#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226626.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_2226626
loop_
_publ_author_name
'Li, Gong-Chun'
'Zhang, Li-Ke'
'Ju, Zhi-Yu'
'Yang, Feng-Ling'
_publ_section_title
;
 1,3-Bis(4-methoxybenzyl)-6-methylpyrimidine-2,4(1H,3H)-dione
;
_journal_coeditor_code           PK2250
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1858
_journal_paper_doi               10.1107/S1600536810024815
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H22 N2 O4'
_chemical_formula_moiety         'C21 H22 N2 O4'
_chemical_formula_sum            'C21 H22 N2 O4'
_chemical_formula_weight         366.41
_chemical_name_systematic
;
1,3-Bis(4-methoxybenzyl)-6-methylpyrimidine-2,4(1H,3H)-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.614(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4133(9)
_cell_length_b                   9.9290(10)
_cell_length_c                   21.407(3)
_cell_measurement_reflns_used    5810
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.90
_cell_volume                     1787.5(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2009)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2009)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2009)'
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2009)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17394
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0556P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                3035
_reflns_number_total             4250
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2250.cif
_cod_data_source_block           I
_cod_original_cell_volume        1787.5(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226626
_cod_database_fobs_code          2226626
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.77270(10) -0.03179(8) 0.39409(4) 0.0326(2) Uani d . 1 . .
O O2 1.05849(10) 0.35414(9) 0.42566(4) 0.0349(2) Uani d . 1 . .
O O3 0.38155(9) 0.43800(8) 0.57937(3) 0.0258(2) Uani d . 1 . .
O O4 1.17640(10) -0.48075(8) 0.20574(4) 0.0286(2) Uani d . 1 . .
N N1 0.91553(10) 0.16121(9) 0.41019(4) 0.0235(2) Uani d . 1 . .
N N2 0.87518(10) 0.07201(9) 0.30901(4) 0.0231(2) Uani d . 1 . .
C C1 0.84910(13) 0.06125(12) 0.37267(5) 0.0244(3) Uani d . 1 . .
C C2 1.00559(13) 0.27014(12) 0.38848(5) 0.0257(3) Uani d . 1 . .
C C3 1.02826(13) 0.27076(12) 0.32258(5) 0.0257(3) Uani d . 1 . .
H H3 1.0893 0.3408 0.3049 0.031 Uiso calc R 1 . .
C C4 0.96571(13) 0.17502(11) 0.28489(5) 0.0234(2) Uani d . 1 . .
C C5 0.99072(15) 0.17657(13) 0.21620(5) 0.0304(3) Uani d . 1 . .
H H5A 1.0646 0.2492 0.2061 0.037 Uiso calc R 1 . .
H H5B 0.8888 0.1915 0.1940 0.037 Uiso calc R 1 . .
H H5C 1.0353 0.0900 0.2034 0.037 Uiso calc R 1 . .
C C6 0.89544(14) 0.14901(13) 0.47867(5) 0.0275(3) Uani d . 1 . .
H H6A 0.9940 0.1808 0.5003 0.033 Uiso calc R 1 . .
H H6B 0.8820 0.0526 0.4891 0.033 Uiso calc R 1 . .
C C7 0.75633(13) 0.22666(12) 0.50352(5) 0.0229(3) Uani d . 1 . .
C C8 0.77921(13) 0.34760(12) 0.53566(5) 0.0244(3) Uani d . 1 . .
H H8 0.8833 0.3838 0.5406 0.029 Uiso calc R 1 . .
C C9 0.65212(13) 0.41528(12) 0.56044(5) 0.0240(3) Uani d . 1 . .
H H9 0.6692 0.4972 0.5825 0.029 Uiso calc R 1 . .
C C10 0.49895(13) 0.36351(11) 0.55308(5) 0.0213(2) Uani d . 1 . .
C C11 0.47377(14) 0.24358(12) 0.52095(5) 0.0250(3) Uani d . 1 . .
H H11 0.3694 0.2080 0.5156 0.030 Uiso calc R 1 . .
C C12 0.60341(13) 0.17605(12) 0.49672(5) 0.0248(3) Uani d . 1 . .
H H12 0.5866 0.0935 0.4751 0.030 Uiso calc R 1 . .
C C13 0.22263(13) 0.38888(13) 0.57144(6) 0.0292(3) Uani d . 1 . .
H H13A 0.1932 0.3867 0.5268 0.035 Uiso calc R 1 . .
H H13B 0.1497 0.4485 0.5933 0.035 Uiso calc R 1 . .
H H13C 0.2160 0.2978 0.5888 0.035 Uiso calc R 1 . .
C C14 0.79638(13) -0.02957(12) 0.26809(6) 0.0263(3) Uani d . 1 . .
H H14A 0.7576 0.0153 0.2293 0.032 Uiso calc R 1 . .
H H14B 0.7027 -0.0656 0.2895 0.032 Uiso calc R 1 . .
C C15 0.90264(13) -0.14602(11) 0.25073(5) 0.0224(2) Uani d . 1 . .
C C16 0.97928(13) -0.22551(12) 0.29611(5) 0.0236(3) Uani d . 1 . .
H H16 0.9686 -0.2036 0.3390 0.028 Uiso calc R 1 . .
C C17 1.06997(13) -0.33503(12) 0.28015(5) 0.0243(3) Uani d . 1 . .
H H17 1.1212 -0.3876 0.3118 0.029 Uiso calc R 1 . .
C C18 1.08652(13) -0.36866(11) 0.21741(5) 0.0224(2) Uani d . 1 . .
C C19 1.01334(13) -0.28976(12) 0.17146(5) 0.0251(3) Uani d . 1 . .
H H19 1.0255 -0.3107 0.1286 0.030 Uiso calc R 1 . .
C C20 0.92206(13) -0.17982(12) 0.18864(5) 0.0249(3) Uani d . 1 . .
H H20 0.8717 -0.1265 0.1570 0.030 Uiso calc R 1 . .
C C21 1.18686(15) -0.52057(13) 0.14183(5) 0.0324(3) Uani d . 1 . .
H H21A 1.0798 -0.5359 0.1241 0.039 Uiso calc R 1 . .
H H21B 1.2489 -0.6038 0.1393 0.039 Uiso calc R 1 . .
H H21C 1.2391 -0.4493 0.1183 0.039 Uiso calc R 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'
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
C10 O3 C13 . . 116.79(9) ?
C18 O4 C21 . . 116.59(9) ?
C1 N1 C2 . . 124.87(9) ?
C1 N1 C6 . . 117.30(9) ?
C2 N1 C6 . . 117.78(9) ?
C4 N2 C1 . . 121.75(9) ?
C4 N2 C14 . . 121.65(9) ?
C1 N2 C14 . . 116.56(9) ?
O1 C1 N1 . . 122.15(11) ?
O1 C1 N2 . . 121.67(10) ?
N1 C1 N2 . . 116.18(10) ?
O2 C2 N1 . . 119.80(10) ?
O2 C2 C3 . . 125.52(11) ?
N1 C2 C3 . . 114.68(10) ?
C4 C3 C2 . . 121.90(11) ?
C4 C3 H3 . . 119.0 ?
C2 C3 H3 . . 119.0 ?
C3 C4 N2 . . 120.60(10) ?
C3 C4 C5 . . 121.37(11) ?
N2 C4 C5 . . 118.03(10) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N1 C6 C7 . . 114.63(9) ?
N1 C6 H6A . . 108.6 ?
C7 C6 H6A . . 108.6 ?
N1 C6 H6B . . 108.6 ?
C7 C6 H6B . . 108.6 ?
H6A C6 H6B . . 107.6 ?
C12 C7 C8 . . 118.64(10) ?
C12 C7 C6 . . 120.28(11) ?
C8 C7 C6 . . 121.04(10) ?
C9 C8 C7 . . 120.71(11) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C10 . . 120.06(11) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
O3 C10 C11 . . 124.45(10) ?
O3 C10 C9 . . 115.51(10) ?
C11 C10 C9 . . 120.04(10) ?
C10 C11 C12 . . 119.15(11) ?
C10 C11 H11 . . 120.4 ?
C12 C11 H11 . . 120.4 ?
C7 C12 C11 . . 121.40(11) ?
C7 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
O3 C13 H13A . . 109.5 ?
O3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N2 C14 C15 . . 114.07(9) ?
N2 C14 H14A . . 108.7 ?
C15 C14 H14A . . 108.7 ?
N2 C14 H14B . . 108.7 ?
C15 C14 H14B . . 108.7 ?
H14A C14 H14B . . 107.6 ?
C20 C15 C16 . . 117.80(10) ?
C20 C15 C14 . . 120.46(10) ?
C16 C15 C14 . . 121.70(10) ?
C17 C16 C15 . . 121.49(10) ?
C17 C16 H16 . . 119.3 ?
C15 C16 H16 . . 119.3 ?
C16 C17 C18 . . 119.94(10) ?
C16 C17 H17 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
O4 C18 C19 . . 124.37(10) ?
O4 C18 C17 . . 116.09(10) ?
C19 C18 C17 . . 119.54(10) ?
C18 C19 C20 . . 119.54(10) ?
C18 C19 H19 . . 120.2 ?
C20 C19 H19 . . 120.2 ?
C15 C20 C19 . . 121.68(10) ?
C15 C20 H20 . . 119.2 ?
C19 C20 H20 . . 119.2 ?
O4 C21 H21A . . 109.5 ?
O4 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O4 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 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
O1 C1 . 1.2220(13) ?
O2 C2 . 1.2276(14) ?
O3 C10 . 1.3677(13) ?
O3 C13 . 1.4288(13) ?
O4 C18 . 1.3723(13) ?
O4 C21 . 1.4292(14) ?
N1 C1 . 1.3848(15) ?
N1 C2 . 1.4070(15) ?
N1 C6 . 1.4853(14) ?
N2 C4 . 1.3838(14) ?
N2 C1 . 1.3904(14) ?
N2 C14 . 1.4803(14) ?
C2 C3 . 1.4290(15) ?
C3 C4 . 1.3444(16) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.4914(15) ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 C7 . 1.5108(15) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C12 . 1.3850(15) ?
C7 C8 . 1.3946(16) ?
C8 C9 . 1.3814(15) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.3922(15) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3886(16) ?
C11 C12 . 1.3929(15) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 C15 . 1.5142(15) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C20 . 1.3850(15) ?
C15 C16 . 1.3954(16) ?
C16 C17 . 1.3770(16) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.3949(15) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.3879(16) ?
C19 C20 . 1.3901(16) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 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
C20 H20 O3 4_665 0.95 2.51 3.3627(14) 150.1
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
C2 N1 C1 O1 . . . . 179.48(10) ?
C6 N1 C1 O1 . . . . 2.11(16) ?
C2 N1 C1 N2 . . . . -0.05(15) ?
C6 N1 C1 N2 . . . . -177.43(9) ?
C4 N2 C1 O1 . . . . -178.01(10) ?
C14 N2 C1 O1 . . . . 4.12(15) ?
C4 N2 C1 N1 . . . . 1.53(15) ?
C14 N2 C1 N1 . . . . -176.34(9) ?
C1 N1 C2 O2 . . . . 179.50(10) ?
C6 N1 C2 O2 . . . . -3.13(15) ?
C1 N1 C2 C3 . . . . -1.11(15) ?
C6 N1 C2 C3 . . . . 176.25(9) ?
O2 C2 C3 C4 . . . . -179.76(12) ?
N1 C2 C3 C4 . . . . 0.89(16) ?
C2 C3 C4 N2 . . . . 0.48(17) ?
C2 C3 C4 C5 . . . . -179.79(10) ?
C1 N2 C4 C3 . . . . -1.78(16) ?
C14 N2 C4 C3 . . . . 175.98(10) ?
C1 N2 C4 C5 . . . . 178.48(10) ?
C14 N2 C4 C5 . . . . -3.75(15) ?
C1 N1 C6 C7 . . . . -95.32(12) ?
C2 N1 C6 C7 . . . . 87.11(12) ?
N1 C6 C7 C12 . . . . 78.75(13) ?
N1 C6 C7 C8 . . . . -103.65(12) ?
C12 C7 C8 C9 . . . . 0.27(16) ?
C6 C7 C8 C9 . . . . -177.37(10) ?
C7 C8 C9 C10 . . . . -0.49(16) ?
C13 O3 C10 C11 . . . . -1.51(15) ?
C13 O3 C10 C9 . . . . 178.71(9) ?
C8 C9 C10 O3 . . . . 179.95(9) ?
C8 C9 C10 C11 . . . . 0.15(16) ?
O3 C10 C11 C12 . . . . -179.39(10) ?
C9 C10 C11 C12 . . . . 0.38(16) ?
C8 C7 C12 C11 . . . . 0.28(16) ?
C6 C7 C12 C11 . . . . 177.94(10) ?
C10 C11 C12 C7 . . . . -0.60(16) ?
C4 N2 C14 C15 . . . . 84.38(13) ?
C1 N2 C14 C15 . . . . -97.75(11) ?
N2 C14 C15 C20 . . . . -126.06(11) ?
N2 C14 C15 C16 . . . . 56.27(14) ?
C20 C15 C16 C17 . . . . -0.72(16) ?
C14 C15 C16 C17 . . . . 177.00(10) ?
C15 C16 C17 C18 . . . . -0.11(16) ?
C21 O4 C18 C19 . . . . -3.25(15) ?
C21 O4 C18 C17 . . . . 176.61(10) ?
C16 C17 C18 O4 . . . . -178.78(9) ?
C16 C17 C18 C19 . . . . 1.09(16) ?
O4 C18 C19 C20 . . . . 178.63(10) ?
C17 C18 C19 C20 . . . . -1.22(16) ?
C16 C15 C20 C19 . . . . 0.58(16) ?
C14 C15 C20 C19 . . . . -177.17(10) ?
C18 C19 C20 C15 . . . . 0.38(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745428
2 PubChem 69181703
