#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/69/2016979.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_2016979
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 O S2'
_chemical_formula_moiety         'C13 H14 N2 O S2'
_chemical_formula_sum            'C13 H14 N2 O S2'
_chemical_formula_weight         278.38
_chemical_name_common            N-methyl-2,4-dithiophenobarbital
_chemical_name_systematic
;
5-ethyl-1-methyl-5-phenyl-2,4-dithioxo-1,2,3,4-tetrahydropyrimidine-
6(5H)-one
;
_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                 103.454(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9600(3)
_cell_length_b                   14.9407(7)
_cell_length_c                   13.1556(10)
_cell_measurement_reflns_used    4532
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1330.47(13)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5152
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_T_max  0.9548
_exptl_absorpt_correction_T_min  0.9159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.292
_refine_ls_extinction_coef       0.017(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   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0462
_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/[σ²(Fo²)+(0.0338P)²+0.7590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1142
_reflns_number_gt                2309
_reflns_number_total             2856
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln3120.cif
_cod_data_source_block           2,4-DTP
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2016979
_cod_database_fobs_code          2016979
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
S S2 0.94383(10) 0.93906(5) 0.10023(5) 0.0561(2) Uani d . 1 . .
S S4 1.11881(8) 0.74572(5) 0.43563(5) 0.0590(2) Uani d . 1 . .
O O6 0.4119(2) 0.84689(13) 0.26619(13) 0.0534(5) Uani d . 1 . .
N N1 0.6625(2) 0.89136(12) 0.19642(12) 0.0376(4) Uani d . 1 . .
C C2 0.8574(3) 0.88936(15) 0.19196(15) 0.0377(5) Uani d . 1 . .
N N3 0.9852(3) 0.84383(13) 0.27062(14) 0.0400(4) Uani d . 1 . .
H H3 1.103(4) 0.8445(16) 0.2669(17) 0.040(6) Uiso d . 1 . .
C C4 0.9435(3) 0.79720(15) 0.35175(16) 0.0381(5) Uani d . 1 . .
C C5 0.7277(3) 0.79573(15) 0.35849(15) 0.0368(5) Uani d . 1 . .
C C6 0.5877(3) 0.84601(15) 0.27097(15) 0.0371(5) Uani d . 1 . .
C C1 0.5201(3) 0.94113(18) 0.11563(17) 0.0486(6) Uani d . 1 . .
H H1A 0.3906 0.9364 0.1290 0.058 Uiso calc R 1 . .
H H1B 0.5187 0.9164 0.0481 0.058 Uiso calc R 1 . .
H H1C 0.5582 1.0030 0.1172 0.058 Uiso calc R 1 . .
C C9 0.7144(3) 0.84385(16) 0.46001(16) 0.0396(5) Uani d . 1 . .
C C10 0.7546(4) 0.93509(18) 0.46874(19) 0.0509(6) Uani d . 1 . .
H H10 0.7900 0.9650 0.4138 0.061 Uiso calc R 1 . .
C C11 0.7429(4) 0.9822(2) 0.5576(2) 0.0615(7) Uani d . 1 . .
H H11 0.7676 1.0434 0.5616 0.074 Uiso calc R 1 . .
C C12 0.6947(4) 0.9381(2) 0.6398(2) 0.0658(8) Uani d . 1 . .
H H12 0.6880 0.9692 0.7001 0.079 Uiso calc R 1 . .
C C13 0.6564(4) 0.8478(2) 0.6326(2) 0.0672(8) Uani d . 1 . .
H H13 0.6241 0.8182 0.6885 0.081 Uiso calc R 1 . .
C C14 0.6652(4) 0.8001(2) 0.54332(19) 0.0543(6) Uani d . 1 . .
H H14 0.6382 0.7390 0.5394 0.065 Uiso calc R 1 . .
C C7 0.6558(3) 0.69729(16) 0.35046(18) 0.0452(5) Uani d . 1 . .
H H7A 0.7326 0.6639 0.4093 0.054 Uiso calc R 1 . .
H H7B 0.5188 0.6958 0.3550 0.054 Uiso calc R 1 . .
C C8 0.6738(4) 0.65186(19) 0.2495(2) 0.0597(7) Uani d . 1 . .
H H8A 0.6280 0.5912 0.2489 0.072 Uiso calc R 1 . .
H H8B 0.8095 0.6521 0.2450 0.072 Uiso calc R 1 . .
H H8C 0.5952 0.6836 0.1909 0.072 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
C2 N1 C6 . . 123.81(17) ?
C2 N1 C1 . . 119.06(17) ?
C6 N1 C1 . . 117.08(17) ?
N1 C2 N3 . . 116.82(17) ?
N1 C2 S2 . . 123.75(15) ?
N3 C2 S2 . . 119.42(15) ?
C4 N3 C2 . . 128.56(18) ?
C4 N3 H3 . . 116.4(16) ?
C2 N3 H3 . . 115.0(16) ?
N3 C4 C5 . . 116.46(17) ?
N3 C4 S4 . . 120.54(15) ?
C5 C4 S4 . . 123.00(15) ?
C6 C5 C4 . . 114.50(16) ?
C6 C5 C9 . . 105.59(17) ?
C4 C5 C9 . . 107.62(17) ?
C6 C5 C7 . . 106.09(17) ?
C4 C5 C7 . . 108.45(18) ?
C9 C5 C7 . . 114.78(17) ?
O6 C6 N1 . . 119.89(18) ?
O6 C6 C5 . . 120.41(18) ?
N1 C6 C5 . . 119.70(16) ?
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 ?
C14 C9 C10 . . 118.6(2) ?
C14 C9 C5 . . 122.8(2) ?
C10 C9 C5 . . 118.56(19) ?
C11 C10 C9 . . 121.2(2) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C12 C11 C10 . . 119.6(3) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C13 C12 C11 . . 119.7(3) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C14 . . 121.1(3) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C9 C14 C13 . . 119.7(3) ?
C9 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C8 C7 C5 . . 113.08(19) ?
C8 C7 H7A . . 109.0 ?
C5 C7 H7A . . 109.0 ?
C8 C7 H7B . . 109.0 ?
C5 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
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
S2 C2 . 1.646(2) ?
S4 C4 . 1.635(2) ?
O6 C6 . 1.210(2) ?
N1 C2 . 1.371(2) ?
N1 C6 . 1.389(3) ?
N1 C1 . 1.475(3) ?
C2 N3 . 1.377(3) ?
N3 C4 . 1.361(3) ?
N3 H3 . 0.83(2) ?
C4 C5 . 1.525(3) ?
C5 C6 . 1.522(3) ?
C5 C9 . 1.538(3) ?
C5 C7 . 1.549(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C9 C14 . 1.386(3) ?
C9 C10 . 1.391(3) ?
C10 C11 . 1.383(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.374(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.374(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.388(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C7 C8 . 1.522(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 O6 1_655 0.83(2) 2.15(2) 2.984(2) 176(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 N3 . . . . -4.1(3) ?
C1 N1 C2 N3 . . . . 178.5(2) ?
C6 N1 C2 S2 . . . . 176.88(17) ?
C1 N1 C2 S2 . . . . -0.5(3) ?
N1 C2 N3 C4 . . . . 2.4(3) ?
S2 C2 N3 C4 . . . . -178.54(19) ?
C2 N3 C4 C5 . . . . -1.0(3) ?
C2 N3 C4 S4 . . . . 178.57(19) ?
N3 C4 C5 C6 . . . . 1.1(3) ?
S4 C4 C5 C6 . . . . -178.51(17) ?
N3 C4 C5 C9 . . . . -116.0(2) ?
S4 C4 C5 C9 . . . . 64.4(2) ?
N3 C4 C5 C7 . . . . 119.3(2) ?
S4 C4 C5 C7 . . . . -60.3(2) ?
C2 N1 C6 O6 . . . . -175.8(2) ?
C1 N1 C6 O6 . . . . 1.7(3) ?
C2 N1 C6 C5 . . . . 4.5(3) ?
C1 N1 C6 C5 . . . . -178.1(2) ?
C4 C5 C6 O6 . . . . 177.5(2) ?
C9 C5 C6 O6 . . . . -64.3(3) ?
C7 C5 C6 O6 . . . . 57.9(3) ?
C4 C5 C6 N1 . . . . -2.7(3) ?
C9 C5 C6 N1 . . . . 115.5(2) ?
C7 C5 C6 N1 . . . . -122.3(2) ?
C6 C5 C9 C14 . . . . 124.0(2) ?
C4 C5 C9 C14 . . . . -113.3(2) ?
C7 C5 C9 C14 . . . . 7.5(3) ?
C6 C5 C9 C10 . . . . -56.4(2) ?
C4 C5 C9 C10 . . . . 66.3(2) ?
C7 C5 C9 C10 . . . . -172.83(19) ?
C14 C9 C10 C11 . . . . -1.1(3) ?
C5 C9 C10 C11 . . . . 179.3(2) ?
C9 C10 C11 C12 . . . . 1.3(4) ?
C10 C11 C12 C13 . . . . -0.7(4) ?
C11 C12 C13 C14 . . . . -0.1(4) ?
C10 C9 C14 C13 . . . . 0.2(3) ?
C5 C9 C14 C13 . . . . 179.9(2) ?
C12 C13 C14 C9 . . . . 0.4(4) ?
C6 C5 C7 C8 . . . . 64.5(2) ?
C4 C5 C7 C8 . . . . -58.9(2) ?
C9 C5 C7 C8 . . . . -179.30(19) ?
