#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008086.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_2008086
loop_
_publ_author_name
'Liu, Y.-F.'
'Chantrapromma, S.'
'Shanmuga Sundara Raj, S.'
'Fun, H.-K.'
'Zhang, Y.-H.'
'Xie, F.-X.'
'Tian, Y.-P.'
'Ni, S.-S.'
_publ_section_title
;
 4-Amino-3-methyl-1,2,4-triazole-5-thione derivative of
 <i>p</i>-nitrophenylaldehyde
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              93
_journal_page_last               94
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C10 H9 N5 O2 S'
_chemical_formula_weight         263.28
_chemical_melting_point          223.6
_chemical_name_systematic
;
3-Methyl-4-amino-5-mercapto-1,2,4-triazole derivative of p-nitro
phenylaldehyde
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 113.881(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3256(5)
_cell_length_b                   6.9775(3)
_cell_length_c                   13.9402(6)
_cell_measurement_reflns_used    2120
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.22
_cell_measurement_theta_min      2.74
_cell_volume                     1185.19(9)
_computing_cell_refinement       'SAINT (Siemens, 1996b)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PARST (Nardelli, 1995)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1996)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device
;
Siemens SMART CCD area-detector diffractometer
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_sigmaI/netI    0.1049
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8482
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   'empirical (SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.036
_refine_ls_goodness_of_fit_obs   1.230
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_restrained_S_obs      1.230
_refine_ls_R_factor_all          0.1853
_refine_ls_R_factor_obs          0.0773
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.2428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1687
_refine_ls_wR_factor_obs         0.1301
_reflns_number_observed          1525
_reflns_number_total             3390
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ha1234.cif
_[local]_cod_data_source_block   I
_cod_original_cell_volume        1185.18(8)
_cod_database_code               2008086
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S 0.0369(5) 0.0974(8) 0.0485(5) -0.0058(5) 0.0130(4) 0.0019(5)
O1 0.0295(14) 0.189(4) 0.132(3) 0.005(2) 0.030(2) -0.015(3)
O2 0.070(2) 0.132(3) 0.137(3) -0.016(2) 0.082(2) -0.021(2)
N1 0.0261(13) 0.076(2) 0.063(2) 0.0001(14) 0.0245(14) -0.002(2)
N2 0.042(2) 0.071(2) 0.066(2) 0.0020(14) 0.037(2) -0.002(2)
N3 0.0229(11) 0.051(2) 0.0456(15) 0.0030(11) 0.0210(11) 0.0049(12)
N4 0.0267(12) 0.050(2) 0.048(2) 0.0008(11) 0.0222(12) 0.0051(12)
N5 0.040(2) 0.077(3) 0.113(3) -0.013(2) 0.046(2) -0.030(2)
C1 0.0245(14) 0.050(2) 0.056(2) 0.0016(14) 0.0199(14) 0.007(2)
C2 0.038(2) 0.052(2) 0.046(2) 0.0061(14) 0.027(2) 0.005(2)
C3 0.050(2) 0.086(3) 0.049(2) 0.007(2) 0.025(2) 0.002(2)
C4 0.027(2) 0.050(2) 0.046(2) 0.0013(14) 0.017(2) 0.008(2)
C5 0.0304(15) 0.040(2) 0.048(2) 0.0001(13) 0.0232(15) 0.0011(14)
C6 0.035(2) 0.065(2) 0.049(2) 0.000(2) 0.022(2) 0.005(2)
C7 0.046(2) 0.071(3) 0.063(2) -0.002(2) 0.039(2) 0.001(2)
C8 0.031(2) 0.054(2) 0.077(3) -0.0045(14) 0.034(2) -0.014(2)
C9 0.029(2) 0.066(3) 0.064(2) 0.000(2) 0.018(2) -0.005(2)
C10 0.037(2) 0.058(2) 0.047(2) 0.003(2) 0.022(2) 0.003(2)
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_occupancy
_atom_site_type_symbol
S 0.94227(7) 0.8384(2) 0.07431(7) 0.0623(4) Uani d 1 S
O1 1.7077(2) 0.8216(6) 0.2939(3) 0.1178(14) Uani d 1 O
O2 1.6478(2) 0.9158(5) 0.1353(3) 0.0999(11) Uani d 1 O
N1 0.9163(2) 0.8762(4) 0.2547(2) 0.0527(8) Uani d 1 N
N2 0.9702(2) 0.9020(4) 0.3611(2) 0.0550(8) Uani d 1 N
N3 1.0839(2) 0.8893(3) 0.2825(2) 0.0376(6) Uani d 1 N
N4 1.1893(2) 0.8847(4) 0.2850(2) 0.0393(6) Uani d 1 N
N5 1.6340(3) 0.8725(5) 0.2134(3) 0.0716(10) Uani d 1 N
C1 0.9808(2) 0.8691(4) 0.2018(2) 0.0424(8) Uani d 1 C
C2 1.0734(2) 0.9079(5) 0.3770(2) 0.0426(8) Uani d 1 C
C3 1.1660(3) 0.9332(8) 0.4786(3) 0.0598(11) Uani d 1 C
C4 1.2024(2) 0.9014(5) 0.2008(3) 0.0408(8) Uani d 1 C
C5 1.3152(2) 0.8959(4) 0.2061(2) 0.0373(7) Uani d 1 C
C6 1.3314(3) 0.9180(5) 0.1145(3) 0.0483(9) Uani d 1 C
C7 1.4354(3) 0.9110(5) 0.1159(3) 0.0548(10) Uani d 1 C
C8 1.5220(2) 0.8815(5) 0.2103(3) 0.0498(9) Uani d 1 C
C9 1.5095(3) 0.8597(5) 0.3027(3) 0.0531(9) Uani d 1 C
C10 1.4049(2) 0.8665(5) 0.3005(3) 0.0457(8) Uani d 1 C
H10 1.393(3) 0.853(4) 0.365(3) 0.054(9) Uiso d 1 H
H4 1.146(3) 0.923(4) 0.136(3) 0.055(10) Uiso d 1 H
H6 1.271(3) 0.928(4) 0.051(2) 0.049(9) Uiso d 1 H
H3C 1.142(4) 0.964(7) 0.533(4) 0.115(17) Uiso d 1 H
H7 1.446(3) 0.921(5) 0.054(3) 0.074(12) Uiso d 1 H
H3B 1.214(4) 1.037(7) 0.479(3) 0.098(16) Uiso d 1 H
H3A 1.214(4) 0.825(7) 0.498(4) 0.108(17) Uiso d 1 H
H9 1.563(3) 0.834(5) 0.363(3) 0.066(12) Uiso d 1 H
H1N1 0.844(3) 0.875(5) 0.228(3) 0.076(12) Uiso d 1 H
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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C1 N1 N2 115.3(3) ?
C2 N2 N1 104.1(3) ?
C1 N3 C2 109.4(2) ?
C1 N3 N4 132.7(2) yes
C2 N3 N4 117.8(2) ?
C4 N4 N3 119.5(2) yes
O1 N5 O2 123.1(3) yes
O1 N5 C8 118.1(4) yes
O2 N5 C8 118.8(4) yes
N1 C1 N3 101.3(3) ?
N1 C1 S 127.4(2) yes
N3 C1 S 131.3(2) ?
N2 C2 N3 110.0(3) ?
N2 C2 C3 125.9(3) yes
N3 C2 C3 124.1(3) ?
N4 C4 C5 118.2(3) yes
C6 C5 C10 119.6(3) ?
C6 C5 C4 119.0(3) ?
C10 C5 C4 121.4(3) ?
C7 C6 C5 120.9(3) ?
C8 C7 C6 118.0(3) ?
C7 C8 C9 122.8(3) ?
C7 C8 N5 118.9(3) yes
C9 C8 N5 118.3(3) ?
C8 C9 C10 118.7(3) ?
C9 C10 C5 120.0(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C1 1.653(3) yes
O1 N5 1.207(4) yes
O2 N5 1.212(4) yes
N1 C1 1.341(4) yes
N1 N2 1.373(4) yes
N2 C2 1.302(4) yes
N3 C1 1.386(3) yes
N3 C2 1.387(4) yes
N3 N4 1.391(3) yes
N4 C4 1.261(4) yes
N5 C8 1.477(4) yes
C2 C3 1.464(5) ?
C4 C5 1.475(4) ?
C5 C6 1.387(4) ?
C5 C10 1.389(4) ?
C6 C7 1.379(4) ?
C7 C8 1.370(5) ?
C8 C9 1.373(5) ?
C9 C10 1.382(4) ?
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
C4 H4 S 1_555 0.93(3) 2.56(3) 3.220(3) 129(3) no
C9 H9 O1 1_555 0.87(3) 2.48(5) 2.706(5) 96(3) no
N1 H1N1 O1 1_455 0.88(4) 2.38(5) 3.066(5) 136(4) yes
N1 H1N1 O2 1_455 0.88(4) 2.42(4) 3.290(4) 170(4) yes