#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/18/2211853.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_2211853
loop_
_publ_author_name
'Ghulam Qadeer'
'Nasim Hasan Rama'
' Muhammad Zareef'
'Xin-Hua Li'
_publ_section_title
5-(4-Methoxyphenyl)-3-(4-nitrobenzylsulfanyl)-4,5-dihydro-3H-1,2,4-triazole
_journal_coeditor_code           HK2168
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o88
_journal_page_last               o89
_journal_paper_doi               10.1107/S1600536806051543
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H14 N4 O3 S'
_chemical_formula_moiety         'C16 H14 N4 O3 S'
_chemical_formula_sum            'C16 H14 N4 O3 S'
_chemical_formula_weight         342.38
_chemical_melting_point          432.0(10)
_chemical_name_systematic
;
5-(4-Methoxyphenyl)-3-(4-nitrobenzylsulfanyl)-4,5-dihydro-3H-1,2,4-triazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.926(4)
_cell_angle_beta                 91.031(4)
_cell_angle_gamma                108.050(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0207(17)
_cell_length_b                   8.1947(18)
_cell_length_c                   12.536(3)
_cell_measurement_reflns_used    1520
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.69
_cell_volume                     780.9(3)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX 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  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4154
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.536
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0916
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0894P)²+1.1058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2185
_refine_ls_wR_factor_ref         0.2269
_reflns_number_gt                2355
_reflns_number_total             2740
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2168.cif
_cod_data_source_block           I
_cod_database_code               2211853
_cod_database_fobs_code          2211853
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S S1 0.29274(18) 0.70340(17) 0.66533(10) 0.0618(5) Uani d . 1
O O1 0.0172(5) -0.2411(5) 0.2066(3) 0.0774(12) Uani d . 1
O O2 0.2948(6) 1.4558(5) 0.9733(4) 0.0852(13) Uani d . 1
O O3 0.1655(7) 1.2833(6) 1.0875(4) 0.1056(17) Uani d . 1
N N1 0.2369(4) 0.4157(4) 0.5425(2) 0.0314(7) Uani d . 1
H H1 0.1497 0.4310 0.5083 0.038 Uiso calc R 1
N N2 0.4600(5) 0.4591(5) 0.6565(3) 0.0559(10) Uani d . 1
N N3 0.4359(5) 0.3019(5) 0.5936(3) 0.0557(10) Uani d . 1
N N4 0.2500(6) 1.3139(5) 1.0082(4) 0.0603(11) Uani d . 1
C C1 0.0756(8) -0.3877(7) 0.1941(6) 0.0842(19) Uani d . 1
H H1A 0.2010 -0.3513 0.1903 0.126 Uiso calc R 1
H H1B 0.0234 -0.4553 0.1295 0.126 Uiso calc R 1
H H1C 0.0419 -0.4558 0.2541 0.126 Uiso calc R 1
C C2 0.0865(6) -0.1217(6) 0.2895(4) 0.0536(12) Uani d . 1
C C3 0.1970(6) -0.1419(6) 0.3710(4) 0.0552(12) Uani d . 1
H H3 0.2253 -0.2435 0.3727 0.066 Uiso calc R 1
C C4 0.2637(6) -0.0103(6) 0.4489(4) 0.0539(12) Uani d . 1
H H4 0.3365 -0.0243 0.5037 0.065 Uiso calc R 1
C C5 0.2248(6) 0.1434(6) 0.4477(3) 0.0450(10) Uani d . 1
C C6 0.1120(6) 0.1602(6) 0.3668(4) 0.0537(12) Uani d . 1
H H6 0.0824 0.2611 0.3655 0.064 Uiso calc R 1
C C7 0.0440(7) 0.0292(7) 0.2889(4) 0.0610(13) Uani d . 1
H H7 -0.0314 0.0420 0.2352 0.073 Uiso calc R 1
C C8 0.3046(6) 0.2836(6) 0.5294(3) 0.0451(10) Uani d . 1
C C9 0.3404(6) 0.5165(6) 0.6222(4) 0.0465(11) Uani d . 1
C C10 0.4321(7) 0.7656(6) 0.7858(4) 0.0551(12) Uani d . 1
H H10A 0.4128 0.6688 0.8296 0.066 Uiso calc R 1
H H10B 0.5546 0.8034 0.7679 0.066 Uiso calc R 1
C C11 0.3851(6) 0.9106(6) 0.8455(4) 0.0468(11) Uani d . 1
C C12 0.4359(6) 1.0741(6) 0.8098(4) 0.0534(12) Uani d . 1
H H12 0.5005 1.0945 0.7485 0.064 Uiso calc R 1
C C13 0.3933(6) 1.2061(6) 0.8622(4) 0.0528(12) Uani d . 1
H H13 0.4278 1.3154 0.8372 0.063 Uiso calc R 1
C C14 0.2980(6) 1.1740(6) 0.9531(4) 0.0468(11) Uani d . 1
C C15 0.2440(6) 1.0123(6) 0.9902(4) 0.0490(11) Uani d . 1
H H15 0.1791 0.9921 1.0514 0.059 Uiso calc R 1
C C16 0.2873(6) 0.8818(5) 0.9358(4) 0.0477(11) Uani d . 1
H H16 0.2504 0.7719 0.9599 0.057 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 0.0016 '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'
S S 0.1484 0.1585 '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'
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
C9 S1 C10 99.5(2) ?
C2 O1 C1 118.6(5) ?
C9 N1 C8 102.4(3) y
C9 N1 H1 128.8 ?
C8 N1 H1 128.8 ?
C9 N2 N3 104.9(4) y
C8 N3 N2 106.1(4) y
O3 N4 O2 122.7(5) ?
O3 N4 C14 117.8(4) ?
O2 N4 C14 119.5(5) ?
O1 C1 H1A 109.5 ?
O1 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
O1 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O1 C2 C7 116.0(5) ?
O1 C2 C3 124.4(5) ?
C7 C2 C3 119.7(5) ?
C4 C3 C2 119.3(4) ?
C4 C3 H3 120.4 ?
C2 C3 H3 120.4 ?
C3 C4 C5 121.5(4) ?
C3 C4 H4 119.3 ?
C5 C4 H4 119.3 ?
C6 C5 C4 118.4(4) ?
C6 C5 C8 121.7(4) ?
C4 C5 C8 119.9(4) ?
C7 C6 C5 120.5(4) ?
C7 C6 H6 119.7 ?
C5 C6 H6 119.7 ?
C6 C7 C2 120.6(5) ?
C6 C7 H7 119.7 ?
C2 C7 H7 119.7 ?
N3 C8 N1 112.5(4) y
N3 C8 C5 128.5(4) ?
N1 C8 C5 119.0(4) ?
N2 C9 N1 114.1(4) y
N2 C9 S1 129.1(4) ?
N1 C9 S1 116.8(3) ?
C11 C10 S1 107.2(3) ?
C11 C10 H10A 110.3 ?
S1 C10 H10A 110.3 ?
C11 C10 H10B 110.3 ?
S1 C10 H10B 110.3 ?
H10A C10 H10B 108.5 ?
C16 C11 C12 118.6(4) ?
C16 C11 C10 120.6(4) ?
C12 C11 C10 120.8(4) ?
C13 C12 C11 121.5(5) ?
C13 C12 H12 119.2 ?
C11 C12 H12 119.2 ?
C12 C13 C14 118.6(4) ?
C12 C13 H13 120.7 ?
C14 C13 H13 120.7 ?
C15 C14 C13 121.3(4) ?
C15 C14 N4 120.0(4) ?
C13 C14 N4 118.6(4) ?
C16 C15 C14 119.0(4) ?
C16 C15 H15 120.5 ?
C14 C15 H15 120.5 ?
C15 C16 C11 121.0(4) ?
C15 C16 H16 119.5 ?
C11 C16 H16 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C9 1.744(5) y
S1 C10 1.809(5) y
O1 C2 1.360(6) ?
O1 C1 1.419(6) ?
O2 N4 1.221(5) ?
O3 N4 1.209(6) ?
N1 C9 1.343(5) y
N1 C8 1.355(5) y
N1 H1 0.8600 ?
N2 C9 1.272(6) y
N2 N3 1.421(6) y
N3 C8 1.279(6) y
N4 C14 1.454(6) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C7 1.381(7) ?
C2 C3 1.393(7) ?
C3 C4 1.372(7) ?
C3 H3 0.9300 ?
C4 C5 1.389(6) ?
C4 H4 0.9300 ?
C5 C6 1.389(6) ?
C5 C8 1.462(6) ?
C6 C7 1.370(7) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C10 C11 1.510(6) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C16 1.380(6) ?
C11 C12 1.383(6) ?
C12 C13 1.363(6) ?
C12 H12 0.9300 ?
C13 C14 1.378(7) ?
C13 H13 0.9300 ?
C14 C15 1.377(6) ?
C15 C16 1.367(6) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
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
C9 N2 N3 C8 -0.1(5)
C1 O1 C2 C7 171.1(5)
C1 O1 C2 C3 -7.7(8)
O1 C2 C3 C4 178.0(5)
C7 C2 C3 C4 -0.8(7)
C2 C3 C4 C5 -0.7(7)
C3 C4 C5 C6 1.7(7)
C3 C4 C5 C8 -177.3(4)
C4 C5 C6 C7 -1.4(7)
C8 C5 C6 C7 177.6(4)
C5 C6 C7 C2 0.0(8)
O1 C2 C7 C6 -177.7(5)
C3 C2 C7 C6 1.1(8)
N2 N3 C8 N1 0.3(5)
N2 N3 C8 C5 -179.9(4)
C9 N1 C8 N3 -0.3(5)
C9 N1 C8 C5 179.9(4)
C6 C5 C8 N3 -163.8(5)
C4 C5 C8 N3 15.1(7)
C6 C5 C8 N1 15.9(6)
C4 C5 C8 N1 -165.1(4)
N3 N2 C9 N1 -0.1(5)
N3 N2 C9 S1 179.1(3)
C8 N1 C9 N2 0.3(5)
C8 N1 C9 S1 -179.0(3)
C10 S1 C9 N2 -10.3(5)
C10 S1 C9 N1 168.8(3)
C9 S1 C10 C11 -170.4(3)
S1 C10 C11 C16 104.8(4)
S1 C10 C11 C12 -73.8(5)
C16 C11 C12 C13 0.8(7)
C10 C11 C12 C13 179.5(4)
C11 C12 C13 C14 0.2(7)
C12 C13 C14 C15 -0.8(7)
C12 C13 C14 N4 -179.0(4)
O3 N4 C14 C15 1.4(7)
O2 N4 C14 C15 -178.2(4)
O3 N4 C14 C13 179.6(5)
O2 N4 C14 C13 0.0(7)
C13 C14 C15 C16 0.4(7)
N4 C14 C15 C16 178.6(4)
C14 C15 C16 C11 0.7(7)
C12 C11 C16 C15 -1.3(7)
C10 C11 C16 C15 -179.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125655
