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_2018297
_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          'C4 H5 N3, 2C7 H10 N2 O S'
_chemical_formula_moiety         'C4 H5 N3, 2(C7 H10 N2 O S)'
_chemical_formula_sum            'C18 H25 N7 O2 S2'
_chemical_formula_weight         435.57
_chemical_name_common
;
2-aminopyrimidine--6-propyl-2-thiouracil (1/2)
;
_chemical_name_systematic
;
2-aminopyrimidine
bis(6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 99.179(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6094(5)
_cell_length_b                   12.9888(6)
_cell_length_c                   20.8838(14)
_cell_measurement_reflns_used    18641
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      3.47
_cell_volume                     2037.7(2)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0937
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25516
_diffrn_reflns_theta_full        25.64
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         3.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.9575
_exptl_absorpt_correction_T_min  0.8442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2009; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.285
_refine_ls_extinction_coef       0.0028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0366
_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/[\s^2^(Fo^2^)+(0.0617P)^2^+0.2289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                3163
_reflns_number_total             3819
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk3414.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018297
_cod_database_fobs_code          2018297