#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/69/2016978.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2016978
loop_
_publ_author_name
'Janik, Alicja'
'Olech, Andrzej'
'Stasiewicz-Urban, Anna'
'Stadnicka, Katarzyna'
_publ_section_title
;
 The influence of sulfur substituents on the molecular geometry and
 packing of thio derivatives of N-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 O2 S'
_chemical_formula_moiety         'C13 H14 N2 O2 S'
_chemical_formula_sum            'C13 H14 N2 O2 S'
_chemical_formula_weight         262.32
_chemical_name_common            N-methyl-4-thiophenobarbital
_chemical_name_systematic
;
5-ethyl-1-methyl-5-phenyl-4-thioxo-3,4-dihydropyrimidine-
2,6(1H,5H)-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.521(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5609(3)
_cell_length_b                   9.5538(3)
_cell_length_c                   11.7268(3)
_cell_measurement_reflns_used    3185
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.131
_cell_measurement_theta_min      0.998
_cell_volume                     1269.13(6)
_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 et al.,  2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method
'φ scans and ω 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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5542
_diffrn_reflns_theta_full        29.16
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(HKL DENZO and SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.407
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0504
_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/[σ²(Fo²)+(0.0603P)²+0.5723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1452
_reflns_number_gt                2494
_reflns_number_total             3381
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln3120.cif
_cod_data_source_block           4-TP
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2016978
_cod_database_fobs_code          2016978
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.85462(13) 0.71786(15) 0.28315(13) 0.0354(3) Uani d . 1 . .
C C1 0.91162(18) 0.7383(2) 0.18288(17) 0.0463(5) Uani d . 1 . .
H H1A 0.9817 0.6820 0.1926 0.056 Uiso calc R 1 . .
H H1B 0.9322 0.8351 0.1778 0.056 Uiso calc R 1 . .
H H1C 0.8582 0.7110 0.1128 0.056 Uiso calc R 1 . .
C C2 0.91090(14) 0.63196(17) 0.37193(15) 0.0339(4) Uani d . 1 . .
O O2 1.00795(11) 0.58274(14) 0.37125(12) 0.0441(3) Uani d . 1 . .
N N3 0.85203(13) 0.60342(17) 0.45992(13) 0.0368(3) Uani d . 1 . .
H H3 0.888(2) 0.542(3) 0.5037(19) 0.050(6) Uiso d . 1 . .
C C4 0.73952(15) 0.64272(18) 0.46494(15) 0.0365(4) Uani d . 1 . .
S S4 0.66585(5) 0.55954(7) 0.54871(5) 0.0586(2) Uani d . 1 . .
C C5 0.69586(15) 0.77289(18) 0.39368(15) 0.0352(4) Uani d . 1 . .
C C6 0.75149(15) 0.78918(18) 0.28659(15) 0.0367(4) Uani d . 1 . .
O O6 0.70851(13) 0.86645(17) 0.20761(12) 0.0567(4) Uani d . 1 . .
C C9 0.73504(15) 0.90006(19) 0.47446(16) 0.0379(4) Uani d . 1 . .
C C10 0.82075(19) 0.9933(2) 0.45587(19) 0.0521(5) Uani d . 1 . .
H H10 0.8603 0.9775 0.3954 0.063 Uiso calc R 1 . .
C C11 0.8486(2) 1.1100(3) 0.5261(2) 0.0666(7) Uani d . 1 . .
H H11 0.9055 1.1725 0.5114 0.080 Uiso calc R 1 . .
C C12 0.7929(2) 1.1340(3) 0.6171(2) 0.0669(7) Uani d . 1 . .
H H12 0.8110 1.2131 0.6633 0.080 Uiso calc R 1 . .
C C13 0.7100(2) 1.0399(3) 0.6393(2) 0.0651(7) Uani d . 1 . .
H H13 0.6731 1.0545 0.7018 0.078 Uiso calc R 1 . .
C C14 0.68137(18) 0.9236(3) 0.56891(19) 0.0540(5) Uani d . 1 . .
H H14 0.6255 0.8604 0.5850 0.065 Uiso calc R 1 . .
C C7 0.56027(16) 0.7752(2) 0.35226(18) 0.0442(4) Uani d . 1 . .
H H7A 0.5242 0.7650 0.4197 0.053 Uiso calc R 1 . .
H H7B 0.5375 0.8660 0.3181 0.053 Uiso calc R 1 . .
C C8 0.5106(2) 0.6631(3) 0.2645(2) 0.0634(6) Uani d . 1 . .
H H8A 0.4263 0.6726 0.2437 0.076 Uiso calc R 1 . .
H H8B 0.5302 0.5724 0.2980 0.076 Uiso calc R 1 . .
H H8C 0.5438 0.6735 0.1962 0.076 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C2 . . 123.39(14) ?
C6 N1 C1 . . 119.02(15) ?
C2 N1 C1 . . 117.53(14) ?
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O2 C2 N3 . . 121.61(16) ?
O2 C2 N1 . . 121.33(16) ?
N3 C2 N1 . . 117.06(14) ?
C4 N3 C2 . . 126.67(15) ?
C4 N3 H3 . . 121.7(16) ?
C2 N3 H3 . . 110.2(16) ?
N3 C4 C5 . . 114.43(15) ?
N3 C4 S4 . . 120.57(14) ?
C5 C4 S4 . . 124.87(13) ?
C4 C5 C6 . . 112.66(14) ?
C4 C5 C7 . . 112.77(15) ?
C6 C5 C7 . . 107.87(15) ?
C4 C5 C9 . . 106.23(14) ?
C6 C5 C9 . . 107.60(14) ?
C7 C5 C9 . . 109.56(14) ?
O6 C6 N1 . . 120.22(16) ?
O6 C6 C5 . . 120.98(16) ?
N1 C6 C5 . . 118.75(14) ?
C10 C9 C14 . . 117.97(19) ?
C10 C9 C5 . . 122.66(17) ?
C14 C9 C5 . . 119.37(17) ?
C9 C10 C11 . . 120.9(2) ?
C9 C10 H10 . . 119.5 ?
C11 C10 H10 . . 119.5 ?
C12 C11 C10 . . 120.5(2) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 C13 . . 119.4(2) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
C12 C13 C14 . . 120.3(2) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C13 C14 C9 . . 120.8(2) ?
C13 C14 H14 . . 119.6 ?
C9 C14 H14 . . 119.6 ?
C8 C7 C5 . . 115.22(16) ?
C8 C7 H7A . . 108.5 ?
C5 C7 H7A . . 108.5 ?
C8 C7 H7B . . 108.5 ?
C5 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 . 1.381(2) ?
N1 C2 . 1.382(2) ?
N1 C1 . 1.471(2) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 O2 . 1.218(2) ?
C2 N3 . 1.372(2) ?
N3 C4 . 1.366(2) ?
N3 H3 . 0.83(2) ?
C4 C5 . 1.527(2) ?
C4 S4 . 1.6297(18) ?
C5 C6 . 1.529(2) ?
C5 C7 . 1.546(2) ?
C5 C9 . 1.551(2) ?
C6 O6 . 1.211(2) ?
C9 C10 . 1.382(3) ?
C9 C14 . 1.392(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.371(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.376(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C7 C8 . 1.516(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 O2 3_766 0.83(3) 2.08(3) 2.902(2) 170(2) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 O2 . . . . -172.10(17) ?
C1 N1 C2 O2 . . . . 5.0(2) ?
C6 N1 C2 N3 . . . . 8.6(2) ?
C1 N1 C2 N3 . . . . -174.25(16) ?
O2 C2 N3 C4 . . . . -174.07(17) ?
N1 C2 N3 C4 . . . . 5.2(3) ?
C2 N3 C4 C5 . . . . -25.1(3) ?
C2 N3 C4 S4 . . . . 158.79(15) ?
N3 C4 C5 C6 . . . . 30.1(2) ?
S4 C4 C5 C6 . . . . -154.03(14) ?
N3 C4 C5 C7 . . . . 152.49(16) ?
S4 C4 C5 C7 . . . . -31.6(2) ?
N3 C4 C5 C9 . . . . -87.48(17) ?
S4 C4 C5 C9 . . . . 88.41(17) ?
C2 N1 C6 O6 . . . . 177.60(18) ?
C1 N1 C6 O6 . . . . 0.5(3) ?
C2 N1 C6 C5 . . . . -0.1(3) ?
C1 N1 C6 C5 . . . . -177.13(16) ?
C4 C5 C6 O6 . . . . 163.18(18) ?
C7 C5 C6 O6 . . . . 38.1(2) ?
C9 C5 C6 O6 . . . . -80.1(2) ?
C4 C5 C6 N1 . . . . -19.2(2) ?
C7 C5 C6 N1 . . . . -144.29(16) ?
C9 C5 C6 N1 . . . . 97.58(18) ?
C4 C5 C9 C10 . . . . 111.14(19) ?
C6 C5 C9 C10 . . . . -9.7(2) ?
C7 C5 C9 C10 . . . . -126.76(19) ?
C4 C5 C9 C14 . . . . -69.7(2) ?
C6 C5 C9 C14 . . . . 169.37(17) ?
C7 C5 C9 C14 . . . . 52.3(2) ?
C14 C9 C10 C11 . . . . -2.8(3) ?
C5 C9 C10 C11 . . . . 176.3(2) ?
C9 C10 C11 C12 . . . . 1.2(4) ?
C10 C11 C12 C13 . . . . 0.9(4) ?
C11 C12 C13 C14 . . . . -1.3(4) ?
C12 C13 C14 C9 . . . . -0.4(4) ?
C10 C9 C14 C13 . . . . 2.4(3) ?
C5 C9 C14 C13 . . . . -176.76(19) ?
C4 C5 C7 C8 . . . . -66.7(2) ?
C6 C5 C7 C8 . . . . 58.3(2) ?
C9 C5 C7 C8 . . . . 175.17(18) ?
