#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/92/2009248.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_2009248
loop_
_publ_author_name
'McCarrick, Robert M.'
'Squattrito, Philip J.'
'Singh, Rajkumar Noren'
'Handa, Ram N.'
'Dubey, Surendra N.'
_publ_section_title
;
 Two Schiff base derivatives of
 4-amino-3-propyl-1,2,4-triazole-5-thione
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2111
_journal_page_last               2114
_journal_paper_doi               10.1107/S0108270199011397
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C13 H16 N4 O S '
_chemical_formula_sum            'C13 H16 N4 O S'
_chemical_formula_weight         276.36
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                99.64(2)
_cell_angle_beta                 95.69(3)
_cell_angle_gamma                90.030(10)
_cell_formula_units_Z            2
_cell_length_a                   9.539(2)
_cell_length_b                   14.177(2)
_cell_length_c                   5.275(2)
_cell_measurement_reflns_used    19
_cell_measurement_temperature    296
_cell_measurement_theta_max      20.5
_cell_measurement_theta_min      15.6
_cell_volume                     699.7(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1988)
;
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation, 1991)
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'MITHRIL (Gilmore, 1983)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Rigaku AFC6S'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2627
_diffrn_reflns_theta_max         25.03
_diffrn_standards_decay_%        0.20
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.31
_refine_ls_abs_structure_details 'not applicable'
_refine_ls_extinction_coef       0.00000
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.23
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2465
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.063
_refine_ls_shift/su_max          0.0081
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 4Fₒ²/σ²(Fₒ²)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.088
_reflns_number_gt                2465
_reflns_number_total             2466
_reflns_threshold_expression     I>0
_cod_data_source_file            da1094.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 35 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        699.8(4)
_cod_original_sg_symbol_H-M      'P -1       '
_cod_original_formula_sum        'C13 H16 N4 O S '
_cod_database_code               2009248
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
'  -x,  -y,  -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
S 0.98352(8) 0.14422(5) 0.3475(2) 0.0650(3) Uani ? ?
O 0.5839(3) 0.3786(2) 0.1941(5) 0.0885(9) Uani ? ?
N1 0.7077(2) 0.26800(10) 0.4787(4) 0.0410(7) Uani ? ?
N2 0.7310(2) 0.17710(10) 0.5491(4) 0.0416(7) Uani ? ?
N3 0.8114(2) 0.0407(2) 0.5882(5) 0.0557(8) Uani ? ?
N4 0.6840(2) 0.04470(10) 0.6930(5) 0.0538(8) Uani ? ?
C1 0.8438(3) 0.1196(2) 0.4966(5) 0.0474(9) Uani ? ?
C2 0.6353(3) 0.1285(2) 0.6635(5) 0.0423(8) Uani ? ?
C3 0.4975(3) 0.1689(2) 0.7335(6) 0.0474(9) Uani ? ?
C4 0.4319(3) 0.1205(2) 0.9257(7) 0.0600(10) Uani ? ?
C5 0.2948(4) 0.1656(3) 0.9970(8) 0.0800(10) Uani ? ?
C6 0.7834(3) 0.3376(2) 0.6204(5) 0.0381(8) Uani ? ?
C7 0.7648(3) 0.4325(2) 0.5429(5) 0.0372(7) Uani ? ?
C8 0.6692(3) 0.4487(2) 0.3383(6) 0.0513(9) Uani ? ?
C9 0.6594(4) 0.5401(2) 0.2706(7) 0.0740(10) Uani ? ?
C10 0.7434(3) 0.6136(2) 0.4029(7) 0.0620(10) Uani ? ?
C11 0.8372(3) 0.6000(2) 0.6031(7) 0.0640(10) Uani ? ?
C12 0.8474(3) 0.5107(2) 0.6729(6) 0.0600(10) Uani ? ?
C13 0.8846(3) 0.3267(2) 0.8476(6) 0.0543(10) Uani ? ?
H1 0.876(2) -0.012(2) 0.601(5) 0.0625 Uani ? ?
H2 0.428(3) 0.163(2) 0.576(5) 0.0592 Uani ? ?
H3 0.511(2) 0.237(2) 0.803(5) 0.0592 Uani ? ?
H4 0.415(3) 0.051(2) 0.847(5) 0.0736 Uani ? ?
H5 0.500(3) 0.123(2) 1.084(5) 0.0737 Uani ? ?
H6 0.248(3) 0.136(2) 1.120(6) 0.0897 Uani ? ?
H7 0.218(3) 0.160(2) 0.842(6) 0.0917 Uani ? ?
H8 0.294(3) 0.229(2) 1.067(6) 0.0897 Uani ? ?
H9 0.612(3) 0.325(2) 0.250(6) 0.1033 Uani ? ?
H10 0.599(3) 0.549(2) 0.122(6) 0.0875 Uani ? ?
H11 0.737(3) 0.674(2) 0.364(5) 0.0731 Uani ? ?
H12 0.903(3) 0.652(2) 0.707(5) 0.0765 Uani ? ?
H13 0.922(3) 0.500(2) 0.816(5) 0.0706 Uani ? ?
H14 0.878(3) 0.270(2) 0.899(5) 0.0642 Uani ? ?
H15 0.882(3) 0.379(2) 0.993(5) 0.0642 Uani ? ?
H16 0.985(3) 0.330(2) 0.797(5) 0.0676 Uani ? ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S 0.110 0.124 'International Tables'
O 0.008 0.006 'International Tables'
N 0.004 0.003 'International Tables'
C 0.002 0.002 'International Tables'
H 0.000 0.000 'International Tables'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -2 -1
0 -4 0
1 -4 -1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C6 114.9(2) yes
N1 N2 C1 126.2(2) yes
N1 N2 C2 124.3(2) yes
C1 N2 C2 109.3(2) yes
N4 N3 C1 114.0(2) yes
N3 N4 C2 104.3(2) yes
S C1 N2 127.4(2) yes
S C1 N3 130.0(2) yes
N2 C1 N3 102.6(2) yes
N2 C2 N4 109.8(2) yes
N2 C2 C3 123.0(2) yes
N4 C2 C3 127.2(2) yes
C2 C3 C4 113.9(2) no
C3 C4 C5 112.1(2) no
N1 C6 C7 115.7(2) yes
N1 C6 C13 124.6(2) yes
C7 C6 C13 119.7(2) yes
C6 C7 C8 122.9(2) no
C6 C7 C12 120.1(2) no
C8 C7 C12 116.9(2) no
O C8 C7 122.8(2) no
O C8 C9 117.1(3) no
C7 C8 C9 120.0(3) no
C8 C9 C10 120.5(3) no
C9 C10 C11 120.8(3) no
C10 C11 C12 119.3(3) no
C7 C12 C11 122.4(3) no
C8 O H9 104(2) no
N4 N3 H1 121.0(10) no
C1 N3 H1 123.0(10) no
C2 C3 H2 110.0(10) no
C2 C3 H3 108.0(10) no
C4 C3 H2 107.0(10) no
C4 C3 H3 109.0(10) no
H2 C3 H3 107.0(10) no
C3 C4 H4 108.0(10) no
C3 C4 H5 109.0(10) no
C5 C4 H4 109.0(10) no
C5 C4 H5 110.0(10) no
H4 C4 H5 107(2) no
C4 C5 H6 114.0(10) no
C4 C5 H7 112.0(10) no
C4 C5 H8 119(2) no
H6 C5 H7 101(2) no
H6 C5 H8 102(2) no
H7 C5 H8 103(2) no
C8 C9 H10 119.0(10) no
C10 C9 H10 119.0(10) no
C9 C10 H11 121.0(10) no
C11 C10 H11 117.0(10) no
C10 C11 H12 124.0(10) no
C12 C11 H12 116.0(10) no
C7 C12 H13 118.0(10) no
C11 C12 H13 118.0(10) no
C6 C13 H14 113.0(10) no
C6 C13 H15 113.0(10) no
C6 C13 H16 108.0(10) no
H14 C13 H15 110(2) no
H14 C13 H16 104(2) no
H15 C13 H16 104(2) no
O H9 N1 150(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S C1 ? ? 1.678(2) yes
O C8 ? ? 1.361(3) yes
N1 N2 ? ? 1.412(2) yes
N1 C6 ? ? 1.303(3) yes
N2 C1 ? ? 1.372(3) yes
N2 C2 ? ? 1.385(3) yes
N3 N4 ? ? 1.381(3) yes
N3 C1 ? ? 1.339(3) yes
N4 C2 ? ? 1.304(3) yes
C2 C3 ? ? 1.490(3) yes
C3 C4 ? ? 1.500(4) no
C4 C5 ? ? 1.509(4) no
C6 C7 ? ? 1.477(3) no
C6 C13 ? ? 1.491(4) no
C7 C8 ? ? 1.392(3) no
C7 C12 ? ? 1.400(4) no
C8 C9 ? ? 1.401(4) no
C9 C10 ? ? 1.364(4) no
C10 C11 ? ? 1.355(4) no
C11 C12 ? ? 1.377(4) no
O H9 ? ? 0.89(3) no
N3 H1 ? ? 0.98(2) no
C3 H2 ? ? 1.00(2) no
C3 H3 ? ? 0.98(2) no
C4 H4 ? ? 1.01(3) no
C4 H5 ? ? 1.00(3) no
C5 H6 ? ? 0.98(3) no
C5 H7 ? ? 1.03(3) no
C5 H8 ? ? 0.91(3) no
C9 H10 ? ? 0.95(3) no
C10 H11 ? ? 0.91(3) no
C11 H12 ? ? 1.02(3) no
C12 H13 ? ? 1.01(2) no
C13 H14 ? ? 0.89(2) no
C13 H15 ? ? 0.97(3) no
C13 H16 ? ? 1.03(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
S C1 N2 N1 2.4(4) no
S C1 N2 C2 177.2(2) no
S C1 N3 N4 -178.0(2) no
O C8 C7 C6 0.7(4) no
O C8 C7 C12 179.2(3) no
O C8 C9 C10 -178.7(3) no
N1 N2 C1 N3 -176.2(2) no
N1 N2 C2 N4 176.8(2) no
N1 N2 C2 C3 -2.1(4) no
N1 C6 C7 C8 2.3(4) no
N1 C6 C7 C12 -176.1(2) no
N2 N1 C6 C7 177.6(2) no
N2 N1 C6 C13 -2.2(4) no
N2 C1 N3 N4 0.6(3) no
N2 C2 N4 N3 -1.5(3) no
N2 C2 C3 C4 -161.7(3) no
N3 N4 C2 C3 177.4(3) no
N3 C1 N2 C2 -1.5(3) no
N4 C2 N2 C1 2.0(3) no
N4 C2 C3 C4 19.6(5) no
C1 N2 N1 C6 -76.7(3) no
C1 N2 C2 C3 -177.0(3) no
C1 N3 N4 C2 0.6(3) no
C2 N2 N1 C6 109.3(3) no
C2 C3 C4 C5 178.3(3) no
C6 C7 C8 C9 -178.3(3) no
C6 C7 C12 C11 177.9(3) no
C7 C8 C9 C10 0.3(5) no
C7 C12 C11 C10 0.5(5) no
C8 C7 C6 C13 -177.9(3) no
C8 C7 C12 C11 -0.6(4) no
C8 C9 C10 C11 -0.4(6) no
C9 C8 C7 C12 0.2(4) no
C9 C10 C11 C12 0.0(5) no
C12 C7 C6 C13 3.7(4) no
