#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/39/2003994.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_2003994
loop_
_publ_author_name
'Toledano, P.'
'Ait Itto, M. Y.'
'Hasnaoui, A.'
_publ_section_title
2-Méthyl-7-phényl-3,5-dithioxo-3,4,5,6-tétrahydro-2H-1,2,4-triazépine
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2066
_journal_page_last               2068
_journal_paper_doi               10.1107/S0108270195001314
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C11 H11 N3 S2'
_chemical_formula_weight         249.538
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 101.600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.122(3)
_cell_length_b                   13.321(2)
_cell_length_c                   7.5090(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.7
_cell_volume                     2363.6(6)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .0101
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -028
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2338
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    .41
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            jaune
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       parallélépipède
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .3
_refine_diff_density_max         .19
_refine_diff_density_min         -0.20
_refine_ls_extinction_coef       'secondaire 57(3)'
_refine_ls_extinction_method     'Larson (1970)'
_refine_ls_goodness_of_fit_obs   3.73
_refine_ls_hydrogen_treatment
'Positions des atomes H: observ\'ees par Fourier diff\'erence et affin\'ees'
_refine_ls_number_parameters     180
_refine_ls_number_reflns         1552
_refine_ls_R_factor_obs          .0327
_refine_ls_shift/esd_max         .004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         .0317
_reflns_number_observed          1552
_reflns_number_total             2079
_reflns_observed_criterion       I>=3\s(I)
_cod_data_source_file            du1107.cif
_cod_data_source_block           du1107a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_weighting_scheme' value ' unit' changed to 'unit' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value ' unit' changed to 'unit'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2363(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2003994
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,-y,1/2+z
-x,-y,-z
-x,y,1/2-z
1/2+x,1/2+y,z
1/2+x,1/2-y,1/2+z
1/2-x,1/2-y,-z
1/2-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
S(1) .53344(3) .78940(6) .01850(10) .0529(5)
S(2) .42171(3) .46429(6) .07330(10) .0515(5)
N(1) .36711(9) .7733(2) -0.1311(3) .0460(10)
N(2) .42196(9) .8030(2) -.0434(3) .047(2)
N(3) .46100(9) .6408(2) .0007(3) .0430(10)
C(1) .46810(10) .7443(2) -.0079(4) .042(2)
C(2) .42050(10) .5873(2) .0597(3) .040(2)
C(3) .37390(10) .6484(2) .1088(4) .043(2)
C(4) .34420(10) .7016(2) -.0602(4) .042(2)
C(5) .42850(10) .9120(3) -.0536(6) .065(3)
C(6) .28650(10) .6715(2) -0.1510(4) .042(2)
C(7) .26540(10) .5772(2) -0.1247(5) .059(2)
C(8) .21120(10) .5512(3) -0.2118(6) .069(3)
C(9) .17760(10) .6184(3) -0.3244(5) .060(2)
C(10) .19850(10) .7118(3) -0.3520(4) .051(2)
C(11) .25230(10) .7386(2) -0.2655(4) .046(2)
H(1) .4943(8) .603(2) -.018(4) .072(3)
H(2) .3930(10) .704(2) .203(3) .072(3)
H(3) .3470(10) .603(2) .168(4) .072(3)
H(4) .4570(10) .935(2) .068(3) .072(3)
H(5) .3870(6) .942(2) -.064(4) .072(3)
H(6) .4480(10) .928(2) -0.167(3) .072(3)
H(7) .2920(10) .524(2) -.043(3) .072(3)
H(8) .1950(10) .4810(10) -0.182(4) .072(3)
H(9) .1348(6) .601(2) -0.382(4) .072(3)
H(10) .1730(10) .764(2) -0.438(3) .072(3)
H(11) .2670(10) .8120(10) -0.280(4) .072(3)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N(2) N(1) C(4) . 117.4(2) yes
N(1) N(2) C(1) . 126.3(2) yes
N(1) N(2) C(5) . 110.8(2) yes
C(1) N(2) C(5) . 119.6(2) yes
C(1) N(3) C(2) . 129.8(2) yes
S(1) C(1) N(2) . 122.8(2) yes
S(1) C(1) N(3) . 118.4(2) yes
N(2) C(1) N(3) . 118.7(2) yes
S(2) C(2) N(3) . 122.7(2) yes
S(2) C(2) C(3) . 122.3(2) yes
N(3) C(2) C(3) . 115.0(2) yes
C(2) C(3) C(4) . 107.7(2) yes
N(1) C(4) C(3) . 122.2(2) yes
N(1) C(4) C(6) . 117.3(2) yes
C(3) C(4) C(6) . 120.5(2) yes
C(4) C(6) C(7) . 121.3(3) yes
C(4) C(6) C(11) . 119.8(3) yes
C(7) C(6) C(11) . 118.9(3) yes
C(6) C(7) C(8) . 119.9(3) yes
C(7) C(8) C(9) . 120.7(3) yes
C(8) C(9) C(10) . 119.6(3) yes
C(9) C(10) C(11) . 120.3(3) yes
C(6) C(11) C(10) . 120.7(3) yes
N(3) H(1) S(2) 3_665 172(3) yes
C(1) N(3) H(1) . 112.9(18) no
C(2) N(3) H(1) . 116.3(18) no
S(1) C(1) H(1) . 92.7(7) no
N(2) C(1) H(1) . 143.1(8) no
N(3) C(1) H(1) . 27.0(7) no
C(2) C(3) H(2) . 107.8(16) no
C(4) C(3) H(2) . 107.8(16) no
C(2) C(3) H(3) . 110.6(17) no
C(4) C(3) H(3) . 113.2(16) no
H(2) C(3) H(3) . 110.(2) no
N(2) C(5) H(4) . 107.2(17) no
N(2) C(5) H(5) . 105.4(17) no
H(4) C(5) H(5) . 112.(2) no
N(2) C(5) H(6) . 108.2(18) no
H(4) C(5) H(6) . 109.(2) no
H(5) C(5) H(6) . 115.(2) no
C(6) C(7) H(7) . 119.4(17) no
C(8) C(7) H(7) . 120.7(17) no
C(7) C(8) H(8) . 118.4(17) no
C(9) C(8) H(8) . 120.7(17) no
C(8) C(9) H(9) . 120.8(17) no
C(10) C(9) H(9) . 119.5(17) no
C(9) C(10) H(10) . 120.3(16) no
C(11) C(10) H(10) . 119.5(17) no
C(6) C(11) H(11) . 119.7(16) no
C(10) C(11) H(11) . 119.5(16) no
N(3) H(1) C(1) . 40.1(12) no
N(3) H(1) C(2) . 37.5(11) no
C(1) H(1) C(2) . 77.3(4) no
C(3) H(2) H(3) . 35.2(11) no
C(3) H(3) H(2) . 35.2(11) no
C(5) H(4) H(5) . 33.7(12) no
C(5) H(4) H(6) . 35.7(12) no
H(5) H(4) H(6) . 61.6(13) no
C(5) H(5) H(4) . 33.9(12) no
C(5) H(5) H(6) . 32.7(12) no
H(4) H(5) H(6) . 58.2(13) no
C(5) H(6) H(4) . 35.7(12) no
C(5) H(6) H(5) . 32.6(12) no
H(4) H(6) H(5) . 60.3(13) no
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
S(1) C(1) . 1.660(3) yes
S(2) C(2) . 1.642(3) yes
N(1) N(2) . 1.411(3) yes
N(1) C(4) . 1.273(3) yes
N(2) C(1) . 1.344(3) yes
N(2) C(5) . 1.463(4) yes
N(3) C(1) . 1.392(3) yes
N(3) C(2) . 1.354(3) yes
C(2) C(3) . 1.492(4) yes
C(3) C(4) . 1.504(4) yes
C(4) C(6) . 1.477(3) yes
C(6) C(7) . 1.384(4) yes
C(6) C(11) . 1.391(4) yes
C(7) C(8) . 1.384(4) yes
C(8) C(9) . 1.378(5) yes
C(8) H(8) . 1.060(10) yes
C(9) C(10) . 1.373(4) yes
C(10) C(11) . 1.376(4) yes
H(1) S(2) 3_665 2.330(10) yes
N(3) S(2) 3_665 3.302(2) yes
S(1) S(2) 3_665 3.6560(10) yes
S(1) C(9) 6_565 3.653(3) yes
S(2) N(3) 2_565 3.455(2) yes
C(3) C(10) 7_565 3.338(4) yes
C(10) C(11) 7_564 3.386(4) yes
N(3) H(1) . 0.980(10) no
C(1) H(1) . 1.99(2) no
C(3) H(2) . 1.060(10) no
C(3) H(3) . 1.060(10) no
C(5) H(4) . 1.070(10) no
C(5) H(5) . 1.070(10) no
C(5) H(6) . 1.070(10) no
C(7) H(7) . 1.060(10) no
C(9) H(9) . 1.063(9) no
C(10) H(10) . 1.050(10) no
C(11) H(11) . 1.060(10) no
H(2) H(3) . 1.73(3) no
H(4) H(5) . 1.78(3) no
H(4) H(6) . 1.74(3) no
H(5) H(6) . 1.80(3) no
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
_geom_torsion_publ_flag
N(2) N(1) C(4) C(6) 179.25 yes
C(4) N(1) N(2) C(1) 57.92 yes
N(1) N(2) C(1) N(3) -22.44 yes
S(1) C(1) N(2) N(1) 155.17 yes
C(5) N(2) N(1) C(4) -143.01 yes
N(2) C(1) N(3) C(2) -33.67 yes
C(2) N(3) C(1) S(1) 148.61 yes
C(1) N(3) C(2) C(3) 5.51 yes
S(2) C(2) N(3) C(1) -175.40 yes
N(3) C(2) C(3) C(4) 62.53 yes
S(2) C(2) C(3) C(4) -116.57 yes
C(2) C(3) C(4) C(6) 109.17 yes
N(1) C(4) C(6) C(11) -21.73 yes
N(1) C(4) C(6) C(7) 158.21 yes
