#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/57/2205789.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_2205789
loop_
_publ_author_name
'Li-Rong Wen'
'Ming Li'
'Zi-Qin Ke'
'Xiao Wang'
_publ_section_title
5-Amino-1-(1,5-dimethyl-1H-pyrazol-4-ylcarbonyl)-3-methylsulfanyl-1H-1,2,4-triazole
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1231
_journal_page_last               o1232
_journal_paper_doi               10.1107/S1600536805010019
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C9 H12 N6 O S'
_chemical_formula_moiety         'C9 H12 N6 O S'
_chemical_formula_sum            'C9 H12 N6 O S'
_chemical_formula_weight         252.31
_chemical_melting_point          514
_chemical_name_systematic
;
5-Amino-1-(1,5-dimethyl-1H-pyrazol-4-ylcarbonyl)-3-methylsulfanyl-
1H-1,2,4-triazole
;
_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                 101.275(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.642(5)
_cell_length_b                   10.100(7)
_cell_length_c                   15.250(10)
_cell_measurement_reflns_used    2811
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.43
_cell_volume                     1154.3(13)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5982
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.504
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.088P)²+0.3815P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                1763
_reflns_number_total             2024
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6057.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2205789
_cod_database_fobs_code          2205789
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_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_type_symbol
S1 0.10096(9) 0.26001(5) 0.73818(4) 0.0513(3) Uani d . 1 S
O1 0.1850(3) 0.14608(17) 0.35938(10) 0.0574(5) Uani d . 1 O
N1 0.3695(3) -0.23200(17) 0.43843(12) 0.0435(5) Uani d . 1 N
N2 0.3390(3) -0.23236(18) 0.52346(14) 0.0508(5) Uani d . 1 N
N3 0.1647(2) 0.18127(17) 0.50250(10) 0.0377(4) Uani d . 1 N
N4 0.1752(2) 0.14103(17) 0.59131(11) 0.0378(4) Uani d . 1 N
N5 0.0756(2) 0.35432(17) 0.57145(11) 0.0419(5) Uani d . 1 N
N6 0.0819(3) 0.3799(2) 0.41826(13) 0.0546(5) Uani d . 1 N
H6A 0.0146 0.4507 0.4224 0.082 Uiso calc R 1 H
H6B 0.0287 0.3293 0.3731 0.082 Uiso calc R 1 H
C1 0.2779(3) -0.1124(2) 0.53426(14) 0.0444(5) Uani d . 1 C
H1 0.2450 -0.0832 0.5865 0.053 Uiso calc R 1 H
C2 0.4291(4) -0.3542(2) 0.40298(19) 0.0599(7) Uani d . 1 C
H2A 0.3311 -0.4152 0.3899 0.090 Uiso calc R 1 H
H2B 0.5234 -0.3926 0.4464 0.090 Uiso calc R 1 H
H2C 0.4721 -0.3354 0.3492 0.090 Uiso calc R 1 H
C3 0.3601(3) -0.0933(2) 0.30431(15) 0.0496(6) Uani d . 1 C
H3A 0.4729 -0.1305 0.2985 0.074 Uiso calc R 1 H
H3B 0.3605 0.0002 0.2929 0.074 Uiso calc R 1 H
H3C 0.2664 -0.1346 0.2620 0.074 Uiso calc R 1 H
C4 0.3301(3) -0.11662(19) 0.39637(13) 0.0365(5) Uani d . 1 C
C5 0.2687(3) -0.03366(19) 0.45695(13) 0.0354(5) Uani d . 1 C
C6 0.2056(3) 0.1000(2) 0.43473(13) 0.0385(5) Uani d . 1 C
C7 0.1192(3) 0.24681(18) 0.62684(14) 0.0376(5) Uani d . 1 C
C8 0.1448(4) 0.0926(2) 0.77486(15) 0.0516(6) Uani d . 1 C
H8A 0.0566 0.0352 0.7410 0.077 Uiso calc R 1 H
H8B 0.1403 0.0861 0.8372 0.077 Uiso calc R 1 H
H8C 0.2611 0.0669 0.7661 0.077 Uiso calc R 1 H
C9 0.1037(3) 0.3110(2) 0.49419(13) 0.0396(5) Uani d . 1 C
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
C7 S1 C8 100.79(10) ?
C4 N1 N2 113.28(17) yes
C4 N1 C2 128.2(2) ?
N2 N1 C2 118.40(19) ?
C1 N2 N1 104.29(17) yes
C9 N3 N4 108.46(15) yes
C9 N3 C6 127.20(17) ?
N4 N3 C6 124.32(17) ?
C7 N4 N3 101.66(16) yes
C9 N5 C7 103.03(18) yes
C9 N6 H6A 109.5 ?
C9 N6 H6B 109.5 ?
H6A N6 H6B 109.5 ?
N2 C1 C5 111.94(19) yes
N2 C1 H1 124.0 ?
C5 C1 H1 124.0 ?
N1 C2 H2A 109.5 ?
N1 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
N1 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
C4 C3 H3A 109.5 ?
C4 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
C4 C3 H3C 109.5 ?
H3A C3 H3C 109.5 ?
H3B C3 H3C 109.5 ?
N1 C4 C5 106.22(18) yes
N1 C4 C3 122.03(18) ?
C5 C4 C3 131.69(19) ?
C4 C5 C1 104.27(19) yes
C4 C5 C6 122.93(18) ?
C1 C5 C6 132.74(19) ?
O1 C6 N3 117.65(19) ?
O1 C6 C5 123.39(19) ?
N3 C6 C5 118.96(18) ?
N4 C7 N5 116.75(19) yes
N4 C7 S1 124.30(15) ?
N5 C7 S1 118.94(15) ?
S1 C8 H8A 109.5 ?
S1 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
S1 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
N5 C9 N6 126.2(2) ?
N5 C9 N3 110.08(17) yes
N6 C9 N3 123.68(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 1.736(2) ?
S1 C8 1.791(3) ?
O1 C6 1.221(3) yes
N1 C4 1.336(3) yes
N1 N2 1.362(3) ?
N1 C2 1.456(3) ?
N2 C1 1.320(3) yes
N3 C9 1.388(3) yes
N3 N4 1.401(2) ?
N3 C6 1.402(3) ?
N4 C7 1.307(3) yes
N5 C9 1.313(3) yes
N5 C7 1.376(3) yes
N6 C9 1.333(3) yes
N6 H6A 0.8900 ?
N6 H6B 0.8900 ?
C1 C5 1.412(3) yes
C1 H1 0.9300 ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C3 C4 1.485(3) ?
C3 H3A 0.9600 ?
C3 H3B 0.9600 ?
C3 H3C 0.9600 ?
C4 C5 1.395(3) yes
C5 C6 1.451(3) ?
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
N6 H6B O1 . 0.89 2.23 2.695(3) 112
N6 H6A N5 3_566 0.89 2.09 2.961(3) 163
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
C4 N1 N2 C1 0.1(3)
C2 N1 N2 C1 -176.6(2)
C9 N3 N4 C7 0.7(2)
C6 N3 N4 C7 -177.77(19)
N1 N2 C1 C5 -0.1(3)
N2 N1 C4 C5 -0.1(2)
C2 N1 C4 C5 176.2(2)
N2 N1 C4 C3 177.6(2)
C2 N1 C4 C3 -6.1(3)
N1 C4 C5 C1 0.0(2)
C3 C4 C5 C1 -177.3(2)
N1 C4 C5 C6 -177.49(18)
C3 C4 C5 C6 5.1(3)
N2 C1 C5 C4 0.1(3)
N2 C1 C5 C6 177.2(2)
C9 N3 C6 O1 -0.6(3)
N4 N3 C6 O1 177.57(19)
C9 N3 C6 C5 179.75(19)
N4 N3 C6 C5 -2.1(3)
C4 C5 C6 O1 7.3(3)
C1 C5 C6 O1 -169.5(2)
C4 C5 C6 N3 -173.12(19)
C1 C5 C6 N3 10.2(3)
N3 N4 C7 N5 -1.2(2)
N3 N4 C7 S1 -179.97(15)
C9 N5 C7 N4 1.2(3)
C9 N5 C7 S1 -179.93(15)
C8 S1 C7 N4 -8.0(2)
C8 S1 C7 N5 173.27(18)
C7 N5 C9 N6 -179.3(2)
C7 N5 C9 N3 -0.7(2)
N4 N3 C9 N5 0.0(2)
C6 N3 C9 N5 178.41(19)
N4 N3 C9 N6 178.7(2)
C6 N3 C9 N6 -2.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129535
