#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/46/2224606.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_2224606
loop_
_publ_author_name
'Li, Gong-Chun'
'Song, Xiao-Ping'
'Zhang, Li-Ke'
'Cui, Jiao-Jiao'
'Yang, Feng-Ling'
_publ_section_title
;
 1,3-Bis(4-methylbenzyl)pyrimidine-2,4(1H,3H)-dione
;
_journal_coeditor_code           CV2673
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o193
_journal_paper_doi               10.1107/S1600536809053586
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H20 N2 O2'
_chemical_formula_moiety         'C20 H20 N2 O2'
_chemical_formula_sum            'C20 H20 N2 O2'
_chemical_formula_weight         320.38
_chemical_name_systematic
;
1,3-Bis(4-methylbenzyl)pyrimidine-2,4(1H,3H)-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                66.25(3)
_cell_angle_beta                 80.79(3)
_cell_angle_gamma                71.18(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4182(19)
_cell_length_b                   10.102(2)
_cell_length_c                   10.448(2)
_cell_measurement_reflns_used    2459
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9123
_cell_measurement_theta_min      2.1308
_cell_volume                     860.7(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8622
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.268
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3001
_refine_ls_restrained_S_all      1.268
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0883
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0409P)²+0.3734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                2529
_reflns_number_total             3001
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv2673.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        860.7(3)
_cod_database_code               2224606
_cod_database_fobs_code          2224606
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.4982(3) 0.1871(3) 0.6026(3) 0.0711(7) Uani d . 1 . .
O O2 0.3392(2) 0.4909(3) 0.8542(2) 0.0661(7) Uani d . 1 . .
N N1 0.4156(2) 0.3369(3) 0.7299(2) 0.0452(6) Uani d . 1 . .
N N2 0.2678(3) 0.5867(3) 0.6284(3) 0.0491(6) Uani d . 1 . .
C C1 0.3407(3) 0.4728(3) 0.7458(3) 0.0483(7) Uani d . 1 . .
C C2 0.6580(3) 0.1972(3) 0.8500(3) 0.0431(7) Uani d . 1 . .
C C3 0.1828(3) 0.7346(3) 0.6372(4) 0.0596(9) Uani d . 1 . .
H H3A 0.1960 0.8147 0.5494 0.072 Uiso calc R 1 . .
H H3B 0.2227 0.7467 0.7105 0.072 Uiso calc R 1 . .
C C4 0.3402(3) 0.4340(4) 0.4937(3) 0.0562(8) Uani d . 1 . .
H H4 0.3370 0.4235 0.4099 0.067 Uiso calc R 1 . .
C C5 0.2677(3) 0.5635(4) 0.5079(3) 0.0543(8) Uani d . 1 . .
H H5 0.2143 0.6422 0.4330 0.065 Uiso calc R 1 . .
C C6 0.7652(3) 0.0843(3) 0.8165(3) 0.0529(8) Uani d . 1 . .
H H6 0.7358 0.0149 0.7973 0.064 Uiso calc R 1 . .
C C7 0.4931(3) 0.2105(3) 0.8525(3) 0.0521(8) Uani d . 1 . .
H H7A 0.4827 0.1170 0.8550 0.063 Uiso calc R 1 . .
H H7B 0.4451 0.2249 0.9372 0.063 Uiso calc R 1 . .
C C8 -0.2911(3) 0.7765(3) 0.7206(3) 0.0492(8) Uani d . 1 . .
C C9 0.4242(3) 0.3092(4) 0.6070(3) 0.0526(8) Uani d . 1 . .
C C10 -0.0848(4) 0.8346(4) 0.5629(3) 0.0577(8) Uani d . 1 . .
H H10 -0.0510 0.8844 0.4730 0.069 Uiso calc R 1 . .
C C11 0.0171(3) 0.7490(3) 0.6673(3) 0.0473(7) Uani d . 1 . .
C C12 0.9150(4) 0.0739(4) 0.8113(3) 0.0614(9) Uani d . 1 . .
H H12 0.9854 -0.0040 0.7901 0.074 Uiso calc R 1 . .
C C13 -0.0374(4) 0.6768(4) 0.7999(3) 0.0599(9) Uani d . 1 . .
H H13 0.0286 0.6189 0.8726 0.072 Uiso calc R 1 . .
C C14 -0.1891(4) 0.6899(3) 0.8254(3) 0.0582(9) Uani d . 1 . .
H H14 -0.2231 0.6392 0.9150 0.070 Uiso calc R 1 . .
C C15 0.9639(4) 0.1749(4) 0.8365(3) 0.0630(10) Uani d . 1 . .
C C16 -0.4572(3) 0.7930(4) 0.7502(4) 0.0696(10) Uani d . 1 . .
H H16A -0.5029 0.8770 0.7787 0.104 Uiso calc R 1 . .
H H16B -0.4712 0.7025 0.8235 0.104 Uiso calc R 1 . .
H H16C -0.5030 0.8099 0.6671 0.104 Uiso calc R 1 . .
C C17 0.7049(4) 0.2967(4) 0.8803(3) 0.0601(9) Uani d . 1 . .
H H17 0.6349 0.3714 0.9064 0.072 Uiso calc R 1 . .
C C18 -0.2361(4) 0.8480(4) 0.5894(4) 0.0610(9) Uani d . 1 . .
H H18 -0.3022 0.9066 0.5168 0.073 Uiso calc R 1 . .
C C19 0.8569(4) 0.2856(4) 0.8720(4) 0.0717(11) Uani d . 1 . .
H H19 0.8869 0.3548 0.8909 0.086 Uiso calc R 1 . .
C C20 1.1291(4) 0.1673(6) 0.8239(4) 0.1041(16) Uani d . 1 . .
H H20A 1.1884 0.0636 0.8601 0.156 Uiso calc R 1 . .
H H20B 1.1462 0.2195 0.8764 0.156 Uiso calc R 1 . .
H H20C 1.1572 0.2137 0.7274 0.156 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
C1 N1 C9 . . 125.6(3) ?
C1 N1 C7 . . 117.3(3) ?
C9 N1 C7 . . 117.1(3) ?
C5 N2 C1 . . 121.7(3) ?
C5 N2 C3 . . 119.8(3) ?
C1 N2 C3 . . 118.5(3) ?
O2 C1 N2 . . 122.4(3) ?
O2 C1 N1 . . 122.7(3) ?
N2 C1 N1 . . 114.9(3) ?
C17 C2 C6 . . 118.5(3) ?
C17 C2 C7 . . 121.2(3) ?
C6 C2 C7 . . 120.3(3) ?
N2 C3 C11 . . 111.9(2) ?
N2 C3 H3A . . 109.2 ?
C11 C3 H3A . . 109.2 ?
N2 C3 H3B . . 109.2 ?
C11 C3 H3B . . 109.2 ?
H3A C3 H3B . . 107.9 ?
C5 C4 C9 . . 120.5(3) ?
C5 C4 H4 . . 119.8 ?
C9 C4 H4 . . 119.8 ?
C4 C5 N2 . . 122.8(3) ?
C4 C5 H5 . . 118.6 ?
N2 C5 H5 . . 118.6 ?
C12 C6 C2 . . 120.5(3) ?
C12 C6 H6 . . 119.8 ?
C2 C6 H6 . . 119.8 ?
N1 C7 C2 . . 112.6(2) ?
N1 C7 H7A . . 109.1 ?
C2 C7 H7A . . 109.1 ?
N1 C7 H7B . . 109.1 ?
C2 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C18 C8 C14 . . 117.5(3) ?
C18 C8 C16 . . 121.4(3) ?
C14 C8 C16 . . 121.1(3) ?
O1 C9 N1 . . 120.2(3) ?
O1 C9 C4 . . 125.3(3) ?
N1 C9 C4 . . 114.4(3) ?
C18 C10 C11 . . 121.3(3) ?
C18 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C10 C11 C13 . . 117.7(3) ?
C10 C11 C3 . . 120.8(3) ?
C13 C11 C3 . . 121.5(3) ?
C6 C12 C15 . . 122.0(3) ?
C6 C12 H12 . . 119.0 ?
C15 C12 H12 . . 119.0 ?
C14 C13 C11 . . 120.7(3) ?
C14 C13 H13 . . 119.6 ?
C11 C13 H13 . . 119.6 ?
C8 C14 C13 . . 121.5(3) ?
C8 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C12 C15 C19 . . 117.3(3) ?
C12 C15 C20 . . 121.7(4) ?
C19 C15 C20 . . 120.9(4) ?
C8 C16 H16A . . 109.5 ?
C8 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C8 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C2 C17 C19 . . 120.1(3) ?
C2 C17 H17 . . 120.0 ?
C19 C17 H17 . . 120.0 ?
C10 C18 C8 . . 121.4(3) ?
C10 C18 H18 . . 119.3 ?
C8 C18 H18 . . 119.3 ?
C15 C19 C17 . . 121.6(3) ?
C15 C19 H19 . . 119.2 ?
C17 C19 H19 . . 119.2 ?
C15 C20 H20A . . 109.5 ?
C15 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C15 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
O1 C9 . 1.221(4) ?
O2 C1 . 1.215(3) ?
N1 C1 . 1.390(4) ?
N1 C9 . 1.405(4) ?
N1 C7 . 1.478(3) ?
N2 C5 . 1.370(4) ?
N2 C1 . 1.386(4) ?
N2 C3 . 1.482(4) ?
C2 C17 . 1.376(4) ?
C2 C6 . 1.381(4) ?
C2 C7 . 1.512(4) ?
C3 C11 . 1.512(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.322(4) ?
C4 C9 . 1.439(4) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C6 C12 . 1.375(4) ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C18 . 1.374(4) ?
C8 C14 . 1.382(4) ?
C8 C16 . 1.513(4) ?
C10 C18 . 1.381(4) ?
C10 C11 . 1.378(4) ?
C10 H10 . 0.9300 ?
C11 C13 . 1.383(4) ?
C12 C15 . 1.371(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.383(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C19 . 1.375(5) ?
C15 C20 . 1.520(4) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C19 . 1.391(4) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
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
C14 H14 O2 2_567 0.93 2.50 3.430(4) 174.3
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
C5 N2 C1 O2 . . . . -178.4(3) ?
C3 N2 C1 O2 . . . . -1.2(4) ?
C5 N2 C1 N1 . . . . 1.6(4) ?
C3 N2 C1 N1 . . . . 178.9(2) ?
C9 N1 C1 O2 . . . . -178.8(3) ?
C7 N1 C1 O2 . . . . 1.1(4) ?
C9 N1 C1 N2 . . . . 1.2(4) ?
C7 N1 C1 N2 . . . . -178.9(2) ?
C5 N2 C3 C11 . . . . 80.2(3) ?
C1 N2 C3 C11 . . . . -97.2(3) ?
C9 C4 C5 N2 . . . . 0.0(5) ?
C1 N2 C5 C4 . . . . -2.2(4) ?
C3 N2 C5 C4 . . . . -179.5(3) ?
C17 C2 C6 C12 . . . . -1.1(4) ?
C7 C2 C6 C12 . . . . 178.7(3) ?
C1 N1 C7 C2 . . . . -95.8(3) ?
C9 N1 C7 C2 . . . . 84.1(3) ?
C17 C2 C7 N1 . . . . 74.8(4) ?
C6 C2 C7 N1 . . . . -105.0(3) ?
C1 N1 C9 O1 . . . . 177.0(3) ?
C7 N1 C9 O1 . . . . -2.8(4) ?
C1 N1 C9 C4 . . . . -3.2(4) ?
C7 N1 C9 C4 . . . . 176.9(2) ?
C5 C4 C9 O1 . . . . -177.7(3) ?
C5 C4 C9 N1 . . . . 2.5(4) ?
C18 C10 C11 C13 . . . . -0.1(5) ?
C18 C10 C11 C3 . . . . 179.8(3) ?
N2 C3 C11 C10 . . . . -103.7(3) ?
N2 C3 C11 C13 . . . . 76.1(4) ?
C2 C6 C12 C15 . . . . -1.1(5) ?
C10 C11 C13 C14 . . . . 0.5(5) ?
C3 C11 C13 C14 . . . . -179.3(3) ?
C18 C8 C14 C13 . . . . 0.8(5) ?
C16 C8 C14 C13 . . . . -178.6(3) ?
C11 C13 C14 C8 . . . . -0.9(5) ?
C6 C12 C15 C19 . . . . 2.1(5) ?
C6 C12 C15 C20 . . . . -177.1(3) ?
C6 C2 C17 C19 . . . . 2.3(5) ?
C7 C2 C17 C19 . . . . -177.5(3) ?
C11 C10 C18 C8 . . . . 0.0(5) ?
C14 C8 C18 C10 . . . . -0.3(5) ?
C16 C8 C18 C10 . . . . 179.0(3) ?
C12 C15 C19 C17 . . . . -0.9(5) ?
C20 C15 C19 C17 . . . . 178.3(3) ?
C2 C17 C19 C15 . . . . -1.3(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23952579
