#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/52/2005286.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_2005286
loop_
_publ_author_name
'Ettorre, A.'
'Mai, A.'
'Artico, M.'
'Massa, S.'
'De Montis, A.'
'La Colla, P.'
_publ_section_title
;
 6-(3-Methylbenzyl)-2-(2-methylpropyl)thio-4(3<i>H</i>)-pyrimidinone
 (DABO 622)
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2115
_journal_page_last               2117
_journal_paper_doi               10.1107/S0108270196006117
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C16 H20 N2 O1 S1'
_chemical_formula_sum            'C16 H20 N2 O S'
_chemical_formula_weight         288.41
_chemical_name_systematic
;
3,4-dihydro-6-(3'-methylbenzyl)-2-(2-methylpropyl)thio-4-oxopyrimidine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_type_scat_source
;
International Tables for X-ray Crystallography (1974, Vol. IV, Tables
2.2A, 2.2C, 2.3.1)
;
_cell_angle_alpha                91.63(2)
_cell_angle_beta                 114.41(9)
_cell_angle_gamma                91.42(2)
_cell_formula_units_Z            2
_cell_length_a                   8.566(2)
_cell_length_b                   14.191(4)
_cell_length_c                   7.246(2)
_cell_measurement_radiation      CuK\a
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      47.4
_cell_measurement_theta_min      31.4
_cell_volume                     801.1(7)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    TEXSAN
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'Rigaku AFC-5R'
_diffrn_measurement_method       'profile data from \w-2\q'
_diffrn_radiation_monochromator  'equatorial mounted graphite'
_diffrn_radiation_source
'Rigaku AFC5R diffractometer on a 12KW rotating anode generator'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2725
_diffrn_reflns_theta_max         62.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.725
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.8
_exptl_absorpt_correction_type
'empirical with \y scan at \c = 90\% (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    none
_exptl_crystal_description       Prism
_exptl_crystal_F_000             308.0
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.90
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1198
_refine_ls_R_factor_obs          0.0560
_refine_ls_shift/esd_max         0.07
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'sigma; w = 1/[\s^2^(F~o~)]'
_refine_ls_wR_factor_obs         0.0670
_reflns_number_observed          1290
_reflns_number_total             2531
_reflns_observed_criterion       >3\s(I)
_cod_data_source_file            na1234.cif
_cod_data_source_block           ettor
_cod_depositor_comments
;
 Updating space group information and adding the symmetry operation list.

 Antanas Vaitkus,
 2018-06-14
;
_cod_original_cell_volume        801.1(4)
_cod_original_formula_sum        'C16 H20 N2 O1 S1'
_cod_database_code               2005286
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0520(10) 0.0800(10) 0.0840(10) -0.0141(8) 0.0420(10) -0.0200(10)
O1 0.069(3) 0.101(4) 0.055(3) -0.021(3) 0.036(2) -0.023(3)
N1 0.047(3) 0.066(3) 0.056(3) -0.005(3) 0.032(3) -0.005(3)
N2 0.048(3) 0.063(3) 0.061(3) -0.003(2) 0.032(3) -0.005(3)
C1 0.075(5) 0.075(5) 0.080(6) -0.002(4) 0.042(5) -0.011(5)
C2 0.075(5) 0.067(5) 0.071(5) 0.004(4) 0.039(4) 0.004(4)
C3 0.042(3) 0.058(4) 0.062(5) 0.001(3) 0.030(3) 0.000(4)
C4 0.073(5) 0.076(5) 0.069(5) 0.009(4) 0.037(4) 0.004(4)
C5 0.092(6) 0.079(6) 0.100(7) 0.018(5) 0.044(5) 0.027(5)
C6 0.093(6) 0.066(5) 0.111(7) 0.005(4) 0.056(6) -0.007(5)
C7 0.180(10) 0.153(9) 0.078(6) -0.013(7) 0.063(7) -0.035(6)
C8 0.050(4) 0.069(4) 0.070(4) -0.003(3) 0.041(3) 0.000(4)
C9 0.041(3) 0.053(4) 0.063(4) 0.001(3) 0.030(3) 0.001(3)
C10 0.041(3) 0.071(4) 0.055(4) -0.006(3) 0.025(3) -0.006(3)
C11 0.052(4) 0.069(4) 0.047(4) 0.000(3) 0.027(3) -0.002(3)
C12 0.046(3) 0.053(4) 0.054(4) -0.002(3) 0.029(3) -0.005(3)
C13 0.059(4) 0.080(5) 0.063(5) -0.012(4) 0.026(4) -0.019(4)
C14 0.079(5) 0.074(5) 0.095(6) -0.012(4) 0.042(5) -0.030(5)
C15 0.151(9) 0.140(8) 0.104(7) 0.002(7) 0.066(7) -0.045(6)
C16 0.149(9) 0.086(6) 0.146(8) -0.011(6) 0.075(7) -0.014(6)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
S1 .2660(2) .3249(1) .5371(3) 5.38(8)
O1 .7121(5) .5317(3) 1.0339(6) 5.7(2)
N1 .5182(6) .4336(3) .7895(7) 4.2(2)
N2 .5639(6) .3695(3) .5156(7) 4.3(2)
C1 .7472(9) .1722(6) .150(1) 5.8(3)
C2 .7578(8) .2659(5) .216(1) 5.4(3)
C3 .8247(7) .2937(4) .419(1) 4.1(3)
C4 .8845(8) .2253(5) .555(1) 5.5(3)
C5 .874(1) .1313(6) .495(1) 7.0(4)
C6 .804(1) .1059(5) .290(1) 6.8(4)
C7 .672(1) .1446(7) -.076(1) 10.7(5)
C8 .8325(7) .3952(4) .4843(9) 4.6(3)
C9 .7232(7) .4126(4) .601(1) 3.9(2)
C10 .7823(7) .4666(4) .7736(9) 4.3(3)
C11 .6740(7) .4818(4) .877(1) 4.3(3)
C12 .4675(7) .3804(4) .6160(9) 3.8(2)
C13 .2348(8) .2728(5) .291(1) 5.4(3)
C14 .3298(9) .1838(5) .296(1) 6.5(4)
C15 .293(1) .1561(6) .075(1) 10.2(5)
C16 .283(1) .1040(6) .393(1) 9.7(5)
H1 .4429 .4378 .8532 5.3
H2 .7183 .3122 .1176 6.5
H3 .9343 .2423 .6949 6.5
H4 .9136 .0848 .5937 8.5
H5 .7962 .0416 .2453 8
H6 .553 .1672 -0.1381 13
H7 .7328 .179 -0.1401 13
H8 .6692 .0813 -0.1012 13
H9 .948 .4135 .5674 5.5
H10 .7917 .4314 .3663 5.5
H11 .8952 .4943 .8251 5.1
H12 .1165 .2579 .2166 6.3
H13 .272 .3183 .2225 6.3
H14 .4508 .1977 .3693 7.6
H15 .1724 .1469 -0.0047 11.6
H16 .3326 .2071 .0149 11.6
H17 .3493 .1012 .0646 11.6
H18 .1628 .0899 .3164 11.6
H19 .3456 .0516 .3857 11.6
H20 .3051 .122 .5263 11.6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C Carbon .017 .009
O Oxygen .047 .032
H Hydrogen .000 .000
N Nitrogen .029 .049
S Sulfur .319 .557
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -2 -1
2 -3 -1
0 -4 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C12 S1 C13 101.6(3) yes
N2 C9 C8 114.4(5) yes
C11 N1 C12 123.4(4) yes
N2 C9 C10 124.2(5) yes
C9 N2 C12 116.1(5) yes
C8 C9 C10 121.5(5) yes
C2 C1 C6 118.6(7) yes
C9 C10 C11 119.5(5) yes
C2 C1 C7 120.8(8) yes
O1 C11 N1 120.8(5) yes
C6 C1 C7 120.6(8) yes
O1 C11 C10 125.4(5) yes
C1 C2 C3 122.6(7) yes
N1 C11 C10 113.8(5) yes
C2 C3 C4 117.1(6) yes
S1 C12 N1 114.8(4) yes
C2 C3 C8 121.1(6) yes
S1 C12 N2 122.3(4) yes
C4 C3 C8 121.8(6) yes
N1 C12 N2 122.9(5) yes
C3 C4 C5 122.1(7) yes
S1 C13 C14 115.8(5) yes
C4 C5 C6 119.1(7) yes
C13 C14 C15 106.7(7) yes
C1 C6 C5 120.5(7) yes
C13 C14 C16 114.8(6) yes
C3 C8 C9 112.0(5) yes
C15 C14 C16 110.0(6) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C12 1.738(5)
S1 C13 1.823(6)
O1 C11 1.237(6)
N1 C11 1.371(7)
N1 C12 1.348(6)
N2 C9 1.363(6)
N2 C12 1.315(6)
C1 C2 1.387(8)
C1 C6 1.350(10)
C1 C7 1.530(10)
C2 C3 1.379(8)
C3 C4 1.356(8)
C3 C8 1.495(8)
C4 C5 1.379(9)
C5 C6 1.390(10)
C8 C9 1.519(7)
C9 C10 1.346(7)
C10 C11 1.432(7)
C13 C14 1.513(9)
C14 C15 1.540(10)
C14 C16 1.480(10)
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
_geom_torsion_publ_flag
N2 C9 C8 C3 -45.2(7) yes
S1 C12 N1 C11 179.0(5) no
C2 C1 C6 C5 -1.0(10) no
S1 C12 N2 C9 -176.1(4) no
C2 C3 C4 C5 -2.2(9) no
S1 C13 C14 C15 -176.9(5) no
C2 C3 C8 C9 116.9(6) no
S1 C13 C14 C16 60.9(8) no
C3 C2 C1 C6 .0(10) no
O1 C11 N1 C12 178.0(6) no
C3 C2 C1 C7 -179.8(6) no
O1 C11 C10 C9 -178.1(6) no
C3 C4 C5 C6 1.0(10) no
N1 C11 C10 C9 2.9(9) no
C3 C8 C9 C10 135.0(6) no
N1 C12 S1 C13 173.9(5) no
C4 C3 C8 C9 -63.9(7) no
N1 C12 N2 C9 2.4(8) no
C5 C4 C3 C8 178.6(6) no
C5 C6 C1 C7 179.0(7) no
N2 C9 C10 C11 .0(10) no
C8 C9 N2 C12 177.9(5) no
N2 C12 S1 C13 -7.5(6) no
C8 C9 C10 C11 179.4(6) no
N2 C12 N1 C11 0.4(9) no
C10 C9 N2 C12 -2.4(9) no
C1 C2 C3 C4 1.4(9) no
C10 C11 N1 C12 -3.0(8) no
C1 C2 C3 C8 -179.4(5) no
C12 S1 C13 C14 77.5(5) no
C1 C6 C5 C4 .0(10) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 135402811