#------------------------------------------------------------------------------
#$Date: 2020-02-29 08:18:25 +0200 (Sat, 29 Feb 2020) $
#$Revision: 248570 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557413.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_1557413
loop_
_publ_author_name
'Doboszewski, Bogdan'
'Nazarenko, Alexander Y.'
'Soares, Fábio da Paixão'
_publ_section_title
;
 1,3-Bis(2-oxopropyl)thymine
;
_journal_coeditor_code           ZQ4039
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x200257
_journal_paper_doi               10.1107/S2414314620002576
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          'C11 H14 N2 O4'
_chemical_formula_moiety         'C11 H14 N2 O4'
_chemical_formula_sum            'C11 H14 N2 O4'
_chemical_formula_weight         238.24
_chemical_melting_point          412
_chemical_name_common
;
1,3-Bis(2-oxopropyl)thymine
;
_chemical_name_systematic
;
5-Methyl-1,3-bis(2-oxopropyl)pyrimidine-2,4(1H,3H)-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.693(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9490(9)
_cell_length_b                   4.9891(3)
_cell_length_c                   17.3647(11)
_cell_measurement_reflns_used    2683
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      3.03
_cell_volume                     1163.42(13)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker PHOTON-100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18736
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.709
_diffrn_reflns_theta_min         3.034
_diffrn_source                   sealedtube
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0421P)²+0.5355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                1889
_reflns_number_total             2458
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zq4039sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1163.41(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1557413
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_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
O O1 0.83624(10) 0.9143(2) 0.36977(7) 0.0433(3) Uani d 1 . .
O O2 0.63791(8) 1.2059(2) 0.24695(7) 0.0361(3) Uani d 1 . .
O O3 0.92187(8) 0.9349(2) 0.18756(7) 0.0378(3) Uani d 1 . .
O O4 0.50121(8) 1.2301(2) 0.06408(7) 0.0364(3) Uani d 1 . .
N N1 0.62809(9) 0.8661(3) 0.15811(7) 0.0258(3) Uani d 1 . .
N N2 0.78007(9) 1.0765(3) 0.21574(7) 0.0244(3) Uani d 1 . .
C C1 0.35466(13) 1.0758(5) 0.09457(13) 0.0579(6) Uani d 1 . .
H H1A 0.333498 1.262010 0.097365 0.087 Uiso calc 0.43(3) . .
H H1B 0.343268 0.974481 0.139636 0.087 Uiso calc 0.43(3) . .
H H1C 0.316192 0.995262 0.044202 0.087 Uiso calc 0.43(3) . .
H H1D 0.328474 0.892492 0.090103 0.087 Uiso calc 0.57(3) . .
H H1E 0.318704 1.180021 0.047833 0.087 Uiso calc 0.57(3) . .
H H1F 0.345780 1.159240 0.143267 0.087 Uiso calc 0.57(3) . .
C C2 0.46300(11) 1.0691(3) 0.09839(9) 0.0285(4) Uani d 1 . .
C C3 0.52141(11) 0.8459(3) 0.14837(10) 0.0291(4) Uani d 1 . .
H H3A 0.50906(19) 0.8483(3) 0.2009(7) 0.035 Uiso calc 1 . .
H H3B 0.4978(3) 0.675(2) 0.1234(3) 0.035 Uiso calc 1 . .
C C4 0.67906(11) 1.0595(3) 0.20955(9) 0.0252(3) Uani d 1 . .
C C5 0.83796(11) 1.2601(3) 0.27622(8) 0.0261(3) Uani d 1 . .
H H5A 0.8008(5) 1.422(2) 0.27574(8) 0.031 Uiso calc 1 . .
H H5B 0.8985(8) 1.3054(7) 0.26324(18) 0.031 Uiso calc 1 . .
C C6 0.86268(11) 1.1388(3) 0.35899(9) 0.0266(3) Uani d 1 . .
C C7 0.91998(12) 1.3150(3) 0.42473(9) 0.0316(4) Uani d 1 . .
H H7A 0.8774(5) 1.456(2) 0.4341(5) 0.047 Uiso calc 1 . .
H H7B 0.9756(8) 1.392(2) 0.4098(3) 0.047 Uiso calc 1 . .
H H7C 0.9440(8) 1.2108(12) 0.4727(6) 0.047 Uiso calc 1 . .
C C8 0.67438(11) 0.7030(3) 0.11540(9) 0.0259(3) Uani d 1 . .
H H8 0.6350(7) 0.574(2) 0.0796(7) 0.031 Uiso calc 1 . .
C C9 0.77188(11) 0.7166(3) 0.12144(8) 0.0250(3) Uani d 1 . .
C C10 0.83202(11) 0.9100(3) 0.17581(9) 0.0254(3) Uani d 1 . .
C C11 0.82282(13) 0.5375(4) 0.07549(10) 0.0347(4) Uani d 1 . .
H H11A 0.7752(6) 0.398(2) 0.0469(7) 0.052 Uiso calc 1 . .
H H11B 0.8811(8) 0.449(2) 0.1132(4) 0.052 Uiso calc 1 . .
H H11C 0.8461(8) 0.6461(12) 0.0358(6) 0.052 Uiso calc 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
C4 N1 C3 . . 117.21(12) ?
C8 N1 C3 . . 120.74(13) ?
C8 N1 C4 . . 122.02(12) ?
C4 N2 C5 . . 116.53(12) ?
C4 N2 C10 . . 125.13(13) ?
C10 N2 C5 . . 117.87(12) ?
H1A C1 H1B . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1A C1 H1D . . 141.1 ?
H1A C1 H1E . . 56.3 ?
H1A C1 H1F . . 56.3 ?
H1B C1 H1C . . 109.5 ?
H1B C1 H1D . . 56.3 ?
H1B C1 H1E . . 141.1 ?
H1B C1 H1F . . 56.3 ?
H1C C1 H1D . . 56.3 ?
H1C C1 H1E . . 56.3 ?
H1C C1 H1F . . 141.1 ?
H1D C1 H1E . . 109.5 ?
H1D C1 H1F . . 109.5 ?
H1E C1 H1F . . 109.5 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
C2 C1 H1E . . 109.5 ?
C2 C1 H1F . . 109.5 ?
O4 C2 C1 . . 122.64(16) ?
O4 C2 C3 . . 122.26(14) ?
C1 C2 C3 . . 115.10(14) ?
N1 C3 C2 . . 113.07(13) ?
N1 C3 H3A . . 109.0 ?
N1 C3 H3B . . 109.0 ?
C2 C3 H3A . . 109.0 ?
C2 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
O2 C4 N1 . . 122.08(13) ?
O2 C4 N2 . . 122.48(14) ?
N1 C4 N2 . . 115.44(13) ?
N2 C5 H5A . . 109.2 ?
N2 C5 H5B . . 109.2 ?
N2 C5 C6 . . 111.84(13) ?
H5A C5 H5B . . 107.9 ?
C6 C5 H5A . . 109.2 ?
C6 C5 H5B . . 109.2 ?
O1 C6 C5 . . 121.18(14) ?
O1 C6 C7 . . 123.40(14) ?
C7 C6 C5 . . 115.42(13) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7B . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N1 C8 H8 . . 118.5 ?
C9 C8 N1 . . 122.96(14) ?
C9 C8 H8 . . 118.5 ?
C8 C9 C10 . . 118.83(14) ?
C8 C9 C11 . . 123.13(14) ?
C10 C9 C11 . . 118.03(13) ?
O3 C10 N2 . . 120.12(14) ?
O3 C10 C9 . . 124.33(14) ?
N2 C10 C9 . . 115.55(12) ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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 C6 . 1.2093(19) ?
O2 C4 . 1.2191(18) ?
O3 C10 . 1.2205(18) ?
O4 C2 . 1.2066(19) ?
N1 C3 . 1.4551(19) ?
N1 C4 . 1.3749(19) ?
N1 C8 . 1.3742(19) ?
N2 C4 . 1.3864(18) ?
N2 C5 . 1.4612(19) ?
N2 C10 . 1.4027(19) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C1 H1D . 0.9800 ?
C1 H1E . 0.9800 ?
C1 H1F . 0.9800 ?
C1 C2 . 1.495(2) ?
C2 C3 . 1.508(2) ?
C3 H3A . 0.972(12) ?
C3 H3B . 0.972(12) ?
C5 H5A . 0.958(12) ?
C5 H5B . 0.958(12) ?
C5 C6 . 1.511(2) ?
C6 C7 . 1.491(2) ?
C7 H7A . 0.962(10) ?
C7 H7B . 0.962(10) ?
C7 H7C . 0.962(10) ?
C8 H8 . 0.959(17) ?
C8 C9 . 1.337(2) ?
C9 C10 . 1.449(2) ?
C9 C11 . 1.499(2) ?
C11 H11A . 0.997(11) ?
C11 H11B . 0.997(11) ?
C11 H11C . 0.997(11) ?
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
C3 H3A O2 2_645 0.973(11) 2.556(6) 3.304(2) 133.7(6)
C3 H3B O4 1_545 0.973(9) 2.453(9) 3.3820(19) 159.7(4)
C5 H5B O3 2_755 0.958(11) 2.504(10) 3.353(2) 147.7(3)
C7 H7A O1 1_565 0.963(9) 2.541(10) 3.2576(19) 131.3(6)
C7 H7B O3 2_755 0.962(11) 2.502(9) 3.370(2) 150.1(6)
C8 H8 O4 1_545 0.958(11) 2.495(10) 3.3213(19) 144.4(9)
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
O4 C2 C3 N1 . . . . 6.9(2) ?
N1 C8 C9 C10 . . . . 0.5(2) ?
N1 C8 C9 C11 . . . . 179.45(14) ?
N2 C5 C6 O1 . . . . 0.6(2) ?
N2 C5 C6 C7 . . . . -178.80(12) ?
C1 C2 C3 N1 . . . . -173.11(16) ?
C3 N1 C4 O2 . . . . 1.3(2) ?
C3 N1 C4 N2 . . . . -178.54(13) ?
C3 N1 C8 C9 . . . . 179.04(14) ?
C4 N1 C3 C2 . . . . 74.43(17) ?
C4 N1 C8 C9 . . . . 1.1(2) ?
C4 N2 C5 C6 . . . . 79.50(16) ?
C4 N2 C10 O3 . . . . -177.28(14) ?
C4 N2 C10 C9 . . . . 3.2(2) ?
C5 N2 C4 O2 . . . . 6.5(2) ?
C5 N2 C4 N1 . . . . -173.64(13) ?
C5 N2 C10 O3 . . . . -5.4(2) ?
C5 N2 C10 C9 . . . . 175.01(12) ?
C8 N1 C3 C2 . . . . -103.59(16) ?
C8 N1 C4 O2 . . . . 179.34(15) ?
C8 N1 C4 N2 . . . . -0.5(2) ?
C8 C9 C10 O3 . . . . 178.02(15) ?
C8 C9 C10 N2 . . . . -2.5(2) ?
C10 N2 C4 O2 . . . . 178.41(14) ?
C10 N2 C4 N1 . . . . -1.7(2) ?
C10 N2 C5 C6 . . . . -93.04(15) ?
C11 C9 C10 O3 . . . . -1.0(2) ?
C11 C9 C10 N2 . . . . 178.53(13) ?

_cod_database_fobs_code 1557413
