The influence of sulfur substituents on the molecular geometry and packing of thio derivatives of <i>N</i>-methylphenobarbital
Janik, Alicja; Olech, Andrzej; Stasiewicz-Urban, Anna; Stadnicka, Katarzyna; Acta Crystallographica Section C 65 (2009) o70–o75; doi:10.1107/S0108270108043060

data_2016981
_publ_section_title
;
 The influence of sulfur substituents on the molecular geometry and
 packing of thio derivatives of <i>N</i>-methylphenobarbital
;
_journal_coeditor_code           LN3120
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o70
_journal_page_last               o75
_journal_paper_doi               10.1107/S0108270108043060
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H14 N2 O3'
_chemical_formula_moiety         'C13 H14 N2 O3'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_chemical_name_common            N-methylphenobarbital
_chemical_name_systematic
;
5-ethyl-1-methyl-5-phenylpyrimidine-2,4,6(1<i>H</i>,3<i>H</i>,5<i>H</i>)-\
trione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.565(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7063(5)
_cell_length_b                   7.2553(2)
_cell_length_c                   12.6606(4)
_cell_measurement_reflns_used    2505
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1212.84(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction
'HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
PLATON (Spek, 2003); ORTEP-3 for Windows (Farrugia, 1997);
MERCURY (Macrae <i>et al.</i>,  2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>,  1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\f scans and \w scans to fill asymmetric unit'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4931
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(HKL DENZO and SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0669P)^2^+0.4169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                2230
_reflns_number_total             2756
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ln3120.cif
_cod_data_source_block           P
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016981
_cod_database_fobs_code          2016981