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_2020472
_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'
_chemical_formula_moiety         'C5 H4 N2 O3 S'
_chemical_formula_sum            'C5 H4 N2 O3 S'
_chemical_formula_weight         172.16
_chemical_name_systematic
;
4-Oxo-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.599(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.409(3)
_cell_length_b                   15.552(3)
_cell_length_c                   7.369(2)
_cell_measurement_reflns_used    5588
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      3.38
_cell_volume                     1296.0(6)
_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 0.997
_diffrn_measured_fraction_theta_max 0.975
_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  0.1491
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9985
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.039
_diffrn_reflns_theta_min         3.378
_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       block
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_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.321
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_reflns         2492
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1632
_refine_ls_R_factor_gt           0.0772
_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^)+(0.0547P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1641
_reflns_number_gt                1294
_reflns_number_total             2492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            eg3200sup1.cif
_cod_data_source_block           VIII
_cod_depositor_comments
'Adding full bibliography for 2020465--2020472.cif.'
_cod_database_code               2020472
_cod_database_fobs_code          2020472
_shelx_estimated_absorpt_t_min   0.896
_shelx_estimated_absorpt_t_max   0.965
_shelx_hkl_checksum              13360
_shelx_res_checksum              8796