New class of bicyclic compounds derived from thiobarbituric acid with representative compound 1,3-diethyl-7-hydroxy-5,5,7-trimethyl- 2-thioxo-1,2,3,5,6,7-hexahydro-4H-pyrano[2,3-d]pyrimidin-4-one. Preparation, crystal structure, mass spectrometry and IR spectroscopy.
N.N. Golovnev; M.S. Molokeev; I.V. Sterkhova; Yu.V. Goryunov; V.V. Atuchin; Journal of Molecular Structure 1102 (2015) 101–107; doi:10.1016/j.molstruc.2015.08.046

data_1529502
_publ_section_title
;
 New class of bicyclic compounds derived from thiobarbituric acid with
 representative compound 1,3-diethyl-7-hydroxy-5,5,7-trimethyl-
 2-thioxo-1,2,3,5,6,7-hexahydro-4H-pyrano[2,3-d]pyrimidin-4-one.
 Preparation, crystal structure, mass spectrometry and IR spectroscopy.
;
_journal_issue                   0
_journal_name_full               'Journal of Molecular Structure'
_journal_page_first              101
_journal_page_last               107
_journal_paper_doi               10.1016/j.molstruc.2015.08.046
_journal_volume                  1102
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H22 N2 O3 S'
_chemical_formula_sum            'C14 H22 N2 O3 S'
_chemical_formula_weight         298.39
_chemical_name_common
;
1,3-diethyl-7-hydroxy-5,5,7-trimethyl-2-thioxo-1,2,3,5,6,7-hexahydro
-4H-pyrano[2,3-d]pyrimidin-4-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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            4
_cell_length_a                   9.7454(4)
_cell_length_b                   11.2225(4)
_cell_length_c                   13.9171(5)
_cell_measurement_temperature    296(2)
_cell_volume                     1522.08(10)
_computing_cell_refinement       'APEX2 (Bruker, 2003-2008)'
_computing_data_collection       'APEX2 (Bruker, 2003-2008)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18798
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.084
_diffrn_reflns_theta_min         2.331
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1. Bruker AXS Inc., Madison, Wisconsin, USA, 2004
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1506 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0444P)^2^+0.4465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3918
_reflns_number_total             4473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            C14H22N2O3S.cif
_cod_data_source_block           c
_cod_database_code               1529502
_cod_database_fobs_code          1529502
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              3503
_shelx_hkl_checksum              63535