6-Propyl-2-thiouracil <i>versus</i> 6-methoxymethyl-2-thiouracil: enhancing the hydrogen-bonded synthon motif by replacement of a methylene group with an O atom
Hützler, Wilhelm Maximilian; Egert, Ernst; Bolte, Michael; Acta Crystallographica Section C 72 (2016) –; doi:10.1107/S2053229616011281

data_2020562
_publ_section_title
;
 6-Propyl-2-thiouracil <i>versus</i> 6-methoxymethyl-2-thiouracil:
 enhancing the hydrogen-bonded synthon motif by replacement of a methylene
 group with an O atom
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229616011281
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C4 H8 N5 +, C6 H7 N2 O2 S -, C6 H8 N2 O2 S'
_chemical_formula_moiety         'C4 H8 N5 +, C6 H7 N2 O2 S -, C6 H8 N2 O2 S'
_chemical_formula_sum            'C16 H23 N9 O4 S2'
_chemical_formula_weight         469.55
_chemical_name_systematic
;
2,4,6-Triaminopyrimidinium
6-methoxymethyl-2-thiouracilate--6-methoxymethyl-2-thiouracil (1/1)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           17
_space_group_name_Hall           'P 2c 2'
_space_group_name_H-M_alt        'P 2 2 21'
_symmetry_space_group_name_Hall  'P 2c 2'
_symmetry_space_group_name_H-M   'P 2 2 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8086(4)
_cell_length_b                   8.1414(5)
_cell_length_c                   18.6651(14)
_cell_measurement_reflns_used    41700
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      3.32
_cell_volume                     1034.64(12)
_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 in SHELXTL-Plus (Sheldrick,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
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_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17255
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.902
_diffrn_reflns_theta_min         3.321
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.180
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.66(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0239
_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/[\s^2^(Fo^2^)+(0.0300P)^2^+0.3621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                1975
_reflns_number_total             1999
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3632sup1.cif
_cod_data_source_block           VII
_cod_database_code               2020562
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.967
_shelx_hkl_checksum              52960
_shelx_res_checksum              31853
_cod_database_fobs_code 2020562