Cocrystals of 6-propyl-2-thiouracil: N—H···O <i>versus</i> N—H···S hydrogen bonds
Tutughamiarso, Maya; Egert, Ernst; Acta Crystallographica Section C 67 (2011) o439–o445; doi:10.1107/S0108270111037991

data_2018298
_publ_section_title
;
 Cocrystals of 6-propyl-2-thiouracil: N---H&#x00B7;&#x00B7;&#x00B7;O
 <i>versus</i> N---H&#x00B7;&#x00B7;&#x00B7;S hydrogen bonds
;
_journal_coeditor_code           SK3414
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o439
_journal_page_last               o445
_journal_paper_doi               10.1107/S0108270111037991
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C9 H11 N3 O2, 2C7 H10 N2 O S'
_chemical_formula_moiety         'C9 H11 N3 O2, 2(C7 H10 N2 O S)'
_chemical_formula_sum            'C23 H31 N7 O4 S2'
_chemical_formula_weight         533.67
_chemical_name_common
;
<i>N</i>-(6-acetamidopyridin-2-yl)acetamide--6-propyl-2-thiouracil (1/2)
;
_chemical_name_systematic
;
<i>N</i>-(6-acetamidopyridin-2-yl)acetamide
bis(6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one)
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            48
_cell_length_a                   37.9355(12)
_cell_length_b                   76.880(3)
_cell_length_c                   10.5666(3)
_cell_measurement_reflns_used    37383
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      3.32
_cell_volume                     30817.3(18)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics
'Mercury (Macrae <i>et al.</i>, 2008) and XP (Sheldrick, 2008);'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       \w
_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  0.1288
_diffrn_reflns_av_sigmaI/netI    0.0827
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       93
_diffrn_reflns_limit_k_min       -93
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            108254
_diffrn_reflns_theta_full        25.66
_diffrn_reflns_theta_max         25.66
_diffrn_reflns_theta_min         3.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_correction_T_min  0.8845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2009; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             13536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.245
_refine_ls_abs_structure_details 'Flack (1983), 6784 Friedel pairs'
_refine_ls_abs_structure_Flack   0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     985
_refine_ls_number_reflns         14445
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                10225
_reflns_number_total             14445
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk3414.cif
_cod_data_source_block           II
_cod_database_code               2018298
_cod_database_fobs_code          2018298