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_2311541
_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          'C12 H20 N2 O2 S2'
_chemical_formula_moiety         'C12 H20 N2 O2 S2'
_chemical_formula_sum            'C12 H20 N2 O2 S2'
_chemical_formula_weight         288.42
_chemical_name_common            'Methitural (Neraval, Thiogenal)'
_chemical_name_systematic
5-(1-Methylbutyl)-5-[2-(methylsulfanyl)ethyl]-2-sulfanylidene-1,3-diazinane-4,6-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 96.0830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.1873(2)
_cell_length_b                   9.09200(10)
_cell_length_c                   20.8684(3)
_cell_measurement_reflns_used    29667
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2865.34(6)
_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) and publCIF Westrip (2010)
;
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker--Nonius APEXII CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24772
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.164
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2813
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0192P)^2^+6.3729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                2630
_reflns_number_total             2813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dx2002sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2311541
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.964
_shelx_hkl_checksum              4567
_shelx_res_checksum              39678
_shelxl_version_number           2014/6