Buthalital and methitural - 5,5-substituted derivatives of 2-thio-barbituric acid forming the same type of hydrogen-bonded chain.
Gelbrich, Thomas; Griesser, Ulrich J.; Acta crystallographica. Section E, Crystallographic communications 73 (2017) 1908–1912; doi:10.1107/S205698901701653X

data_2311540
_publ_section_title
;
 Buthalital and methitural - 5,5-substituted derivatives of
 2-thio-barbituric acid forming the same type of hydrogen-bonded chain.
;
_journal_coeditor_code           DX2002
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1908
_journal_page_last               1912
_journal_paper_doi               10.1107/S205698901701653X
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C11 H16 N2 O2 S'
_chemical_formula_moiety         'C11 H16 N2 O2 S'
_chemical_formula_sum            'C11 H16 N2 O2 S'
_chemical_formula_weight         240.32
_chemical_name_common
'Buthalital (Bayinal, Baytinal, Thialbutal, Transithal, Ulbreval)'
_chemical_name_systematic
;
5-(2-Methylpropyl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 96.539(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7271(6)
_cell_length_b                   11.6521(4)
_cell_length_c                   12.5400(8)
_cell_measurement_reflns_used    10435
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1266.88(13)
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_collection
;
COLLECT (Hooft, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae <i>et al.</i>,
2006)
;
_computing_publication_material
;
PLATON (Spek, 2009), publCIF (Westrip, 2010) and <i>TOPOS</i>
(Blatov, 2006)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type
'Bruker--Nonius Roper CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9476
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         3.270
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.269
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0431P)^2^+0.2810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                1833
_reflns_number_total             2519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dx2002sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1266.89(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2311540
_shelx_estimated_absorpt_t_min   0.909
_shelx_estimated_absorpt_t_max   0.988
_shelx_hkl_checksum              74414
_shelx_res_checksum              13363
_shelxl_version_number           2014/6