#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/69/2016980.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_2016980
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 S3'
_chemical_formula_moiety         'C13 H14 N2 S3'
_chemical_formula_sum            'C13 H14 N2 S3'
_chemical_formula_weight         294.44
_chemical_name_common            N-methyl-2,4,6-trithiophenobarbital
_chemical_name_systematic
;
5-ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrithione
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.6810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8686(2)
_cell_length_b                   7.2346(4)
_cell_length_c                   14.9844(5)
_cell_measurement_reflns_used    5864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1406.56(9)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5585
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.9049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(HKL DENZO and SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.375
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0478
_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)+(0.0378P)²+0.9914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                2587
_reflns_number_total             3201
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln3120.cif
_cod_data_source_block           2,4,6-TTP
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2016980
_cod_database_fobs_code          2016980
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 0.62364(7) 0.57579(12) 0.67308(7) 0.0697(3) Uani d . 1 . .
S S4 0.59290(5) 1.07522(10) 0.41969(5) 0.0516(2) Uani d . 1 . .
S S6 0.97026(5) 0.84366(11) 0.65166(5) 0.0541(2) Uani d . 1 . .
N N1 0.79393(14) 0.7041(3) 0.64856(12) 0.0367(4) Uani d . 1 . .
C C2 0.68854(18) 0.7062(3) 0.62460(16) 0.0395(5) Uani d . 1 . .
N N3 0.63592(14) 0.8345(3) 0.55717(14) 0.0399(4) Uani d D 1 . .
H H3 0.5714(9) 0.849(4) 0.5512(18) 0.048 Uiso d D 1 . .
C C4 0.67072(16) 0.9342(3) 0.49844(15) 0.0331(5) Uani d . 1 . .
C C5 0.78160(15) 0.8976(3) 0.50722(14) 0.0293(4) Uani d . 1 . .
C C6 0.84561(16) 0.8160(3) 0.60545(15) 0.0333(5) Uani d . 1 . .
C C1 0.8537(2) 0.5882(4) 0.73020(19) 0.0559(7) Uani d . 1 . .
H H1A 0.9257 0.5982 0.7399 0.067 Uiso calc R 1 . .
H H1B 0.8323 0.4618 0.7174 0.067 Uiso calc R 1 . .
H H1C 0.8420 0.6292 0.7865 0.067 Uiso calc R 1 . .
C C9 0.78163(16) 0.7428(3) 0.43490(14) 0.0311(4) Uani d . 1 . .
C C10 0.69749(18) 0.6297(3) 0.39136(16) 0.0400(5) Uani d . 1 . .
H H10 0.6375 0.6460 0.4047 0.048 Uiso calc R 1 . .
C C11 0.7015(2) 0.4927(4) 0.32819(18) 0.0493(6) Uani d . 1 . .
H H11 0.6442 0.4180 0.2998 0.059 Uiso calc R 1 . .
C C12 0.7891(2) 0.4662(4) 0.30713(18) 0.0537(7) Uani d . 1 . .
H H12 0.7915 0.3745 0.2645 0.064 Uiso calc R 1 . .
C C13 0.8734(2) 0.5772(4) 0.3501(2) 0.0579(7) Uani d . 1 . .
H H13 0.9330 0.5603 0.3361 0.069 Uiso calc R 1 . .
C C14 0.87040(18) 0.7135(4) 0.41367(18) 0.0466(6) Uani d . 1 . .
H H14 0.9283 0.7865 0.4426 0.056 Uiso calc R 1 . .
C C7 0.82923(17) 1.0775(3) 0.48562(16) 0.0368(5) Uani d . 1 . .
H H7A 0.8986 1.0507 0.4878 0.044 Uiso calc R 1 . .
H H7B 0.7894 1.1161 0.4211 0.044 Uiso calc R 1 . .
C C8 0.8343(2) 1.2379(4) 0.5529(2) 0.0533(7) Uani d . 1 . .
H H8A 0.8649 1.3431 0.5342 0.064 Uiso calc R 1 . .
H H8B 0.8752 1.2029 0.6169 0.064 Uiso calc R 1 . .
H H8C 0.7659 1.2687 0.5499 0.064 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 . . 123.34(18) ?
C2 N1 C1 . . 117.2(2) ?
C6 N1 C1 . . 119.2(2) ?
N3 C2 N1 . . 115.95(19) ?
N3 C2 S2 . . 118.78(18) ?
N1 C2 S2 . . 125.21(17) ?
C4 N3 C2 . . 128.24(19) ?
C4 N3 H3 . . 117.2(17) ?
C2 N3 H3 . . 114.5(18) ?
N3 C4 C5 . . 115.71(18) ?
N3 C4 S4 . . 120.26(16) ?
C5 C4 S4 . . 123.94(16) ?
C4 C5 C6 . . 111.90(16) ?
C4 C5 C7 . . 109.25(17) ?
C6 C5 C7 . . 112.20(17) ?
C4 C5 C9 . . 108.28(16) ?
C6 C5 C9 . . 104.30(16) ?
C7 C5 C9 . . 110.76(16) ?
N1 C6 C5 . . 116.81(18) ?
N1 C6 S6 . . 121.32(16) ?
C5 C6 S6 . . 121.62(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 ?
C10 C9 C14 . . 117.9(2) ?
C10 C9 C5 . . 123.02(19) ?
C14 C9 C5 . . 119.05(19) ?
C9 C10 C11 . . 120.9(2) ?
C9 C10 H10 . . 119.5 ?
C11 C10 H10 . . 119.5 ?
C12 C11 C10 . . 120.6(2) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 C13 . . 119.0(2) ?
C11 C12 H12 . . 120.5 ?
C13 C12 H12 . . 120.5 ?
C12 C13 C14 . . 120.8(3) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C13 C14 C9 . . 120.7(2) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
C8 C7 C5 . . 115.24(19) ?
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
S2 C2 . 1.640(2) ?
S4 C4 . 1.643(2) ?
S6 C6 . 1.632(2) ?
N1 C2 . 1.377(3) ?
N1 C6 . 1.383(3) ?
N1 C1 . 1.473(3) ?
C2 N3 . 1.376(3) ?
N3 C4 . 1.352(3) ?
N3 H3 . 0.873(10) ?
C4 C5 . 1.520(3) ?
C5 C6 . 1.543(3) ?
C5 C7 . 1.544(3) ?
C5 C9 . 1.558(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C9 C10 . 1.385(3) ?
C9 C14 . 1.392(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.372(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.376(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.382(3) ?
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 S4 3_676 0.870(10) 2.530(10) 3.376(2) 164(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 . . . . -3.1(3) ?
C1 N1 C2 N3 . . . . 171.2(2) ?
C6 N1 C2 S2 . . . . 179.65(17) ?
C1 N1 C2 S2 . . . . -6.0(3) ?
N1 C2 N3 C4 . . . . 13.8(4) ?
S2 C2 N3 C4 . . . . -168.8(2) ?
C2 N3 C4 C5 . . . . 0.9(3) ?
C2 N3 C4 S4 . . . . 177.6(2) ?
N3 C4 C5 C6 . . . . -23.0(3) ?
S4 C4 C5 C6 . . . . 160.47(16) ?
N3 C4 C5 C7 . . . . -147.9(2) ?
S4 C4 C5 C7 . . . . 35.6(2) ?
N3 C4 C5 C9 . . . . 91.4(2) ?
S4 C4 C5 C9 . . . . -85.1(2) ?
C2 N1 C6 C5 . . . . -19.9(3) ?
C1 N1 C6 C5 . . . . 165.8(2) ?
C2 N1 C6 S6 . . . . 165.80(17) ?
C1 N1 C6 S6 . . . . -8.4(3) ?
C4 C5 C6 N1 . . . . 32.1(2) ?
C7 C5 C6 N1 . . . . 155.33(18) ?
C9 C5 C6 N1 . . . . -84.7(2) ?
C4 C5 C6 S6 . . . . -153.62(16) ?
C7 C5 C6 S6 . . . . -30.4(2) ?
C9 C5 C6 S6 . . . . 89.54(19) ?
C4 C5 C9 C10 . . . . -15.5(3) ?
C6 C5 C9 C10 . . . . 103.8(2) ?
C7 C5 C9 C10 . . . . -135.3(2) ?
C4 C5 C9 C14 . . . . 165.6(2) ?
C6 C5 C9 C14 . . . . -75.1(2) ?
C7 C5 C9 C14 . . . . 45.8(3) ?
C14 C9 C10 C11 . . . . -0.4(3) ?
C5 C9 C10 C11 . . . . -179.4(2) ?
C9 C10 C11 C12 . . . . -0.1(4) ?
C10 C11 C12 C13 . . . . 0.3(4) ?
C11 C12 C13 C14 . . . . 0.1(4) ?
C12 C13 C14 C9 . . . . -0.7(4) ?
C10 C9 C14 C13 . . . . 0.8(4) ?
C5 C9 C14 C13 . . . . 179.8(2) ?
C4 C5 C7 C8 . . . . 61.5(2) ?
C6 C5 C7 C8 . . . . -63.2(2) ?
C9 C5 C7 C8 . . . . -179.32(19) ?
