Eight new crystal structures of 5-(hydroxymethyl)uracil, 5-carboxyuracil and 5-carboxy-2-thiouracil: insights into the hydrogen-bonded networks and the predominant conformations of the C5-bound residues
Seiler, Vanessa Kristina; Hützler, Wilhelm Maximilian; Bolte, Michael; Acta Crystallographica Section C 72 (2016) 379–388; doi:10.1107/S2053229616004861

data_2020471
_publ_section_title
;
 Eight new crystal structures of 5-(hydroxymethyl)uracil, 5-carboxyuracil
 and 5-carboxy-2-thiouracil: insights into the hydrogen-bonded networks
 and the predominant conformations of the C5-bound residues
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              379
_journal_page_last               388
_journal_paper_doi               10.1107/S2053229616004861
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C5 H4 N2 O3 S, 1.5C4 H8 O2'
_chemical_formula_moiety         'C5 H4 N2 O3 S, 1.5(C4 H8 O2)'
_chemical_formula_sum            'C11 H16 N2 O6 S'
_chemical_formula_weight         304.32
_chemical_name_systematic
;
4-Oxo-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid
1,4-dioxane sesquisolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                89.377(10)
_cell_angle_beta                 85.143(10)
_cell_angle_gamma                77.700(10)
_cell_formula_units_Z            2
_cell_length_a                   5.2819(7)
_cell_length_b                   10.3542(12)
_cell_length_c                   13.0071(15)
_cell_measurement_reflns_used    6794
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.12
_cell_measurement_theta_min      3.72
_cell_volume                     692.51(15)
_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 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5885
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.825
_diffrn_reflns_theta_min         3.722
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2645
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0652P)^2^+0.0475P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                2272
_reflns_number_total             2645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            eg3200sup1.cif
_cod_data_source_block           VII
_cod_depositor_comments
'Adding full bibliography for 2020465--2020472.cif.'
_cod_database_code               2020471
_cod_database_fobs_code          2020471
_shelx_estimated_absorpt_t_min   0.926
_shelx_estimated_absorpt_t_max   0.959
_shelx_hkl_checksum              32433
_shelx_res_checksum              25264