#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/23/8102353.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102353
loop_
_publ_author_name
'Qi-Chun Ding'
'Yu-Lin Huang'
'Yun-Ti Sun'
'Jing Zhang'
'Li-Xue Zhang'
'Xiao-Dan Fu'
_publ_section_title
;
 Crystal structure of
 (E)-4-(benzylideneamino)-3-(2-ethoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione,
 C17H16N4OS
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              101
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C17 H16 N4 O S'
_chemical_formula_sum            'C17 H16 N4 O S'
_chemical_formula_weight         324.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.177(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9578(9)
_cell_length_b                   15.4656(18)
_cell_length_c                   13.9638(16)
_cell_measurement_reflns_used    2494
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.88
_cell_measurement_theta_min      2.64
_cell_volume                     1717.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL(Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10361
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             680.0
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0733
_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)+(0.0624P)²+0.5690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                3065
_reflns_number_total             4266
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2423.cff
_cod_data_source_block           dd
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8102353
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.74798(9) 1.06013(5) 0.94862(5) 0.0628(3) Uani 1 1 d . . .
N2 N 0.5530(3) 0.92179(14) 0.89869(15) 0.0499(5) Uani 1 1 d . . .
N3 N 0.7577(2) 0.93453(13) 0.80832(13) 0.0442(5) Uani 1 1 d . . .
N4 N 0.8835(3) 0.96525(15) 0.74974(14) 0.0526(5) Uani 1 1 d . . .
N1 N 0.5336(3) 0.85585(14) 0.83366(15) 0.0499(5) Uani 1 1 d . . .
C9 C 0.6598(3) 0.86547(16) 0.77883(16) 0.0436(5) Uani 1 1 d . . .
C8 C 0.6998(3) 0.81219(16) 0.69570(17) 0.0481(6) Uani 1 1 d . . .
C3 C 0.8555(3) 0.77163(17) 0.69256(19) 0.0534(6) Uani 1 1 d . . .
C7 C 0.5849(4) 0.8037(2) 0.6192(2) 0.0660(8) Uani 1 1 d . . .
H7 H 0.4790 0.8287 0.6222 0.079 Uiso 1 1 calc R . .
C4 C 0.8983(4) 0.7280(2) 0.6098(2) 0.0701(8) Uani 1 1 d . . .
H4 H 1.0038 0.7027 0.6059 0.084 Uiso 1 1 calc R . .
C6 C 0.6276(5) 0.7583(2) 0.5387(2) 0.0824(10) Uani 1 1 d . . .
H6 H 0.5502 0.7520 0.4876 0.099 Uiso 1 1 calc R . .
C2 C 1.1115(4) 0.7341(2) 0.7793(3) 0.0807(10) Uani 1 1 d . . .
H2A H 1.1915 0.7647 0.7410 0.097 Uiso 1 1 calc R . .
H2B H 1.1004 0.6755 0.7550 0.097 Uiso 1 1 calc R . .
C5 C 0.7839(5) 0.7227(2) 0.5343(2) 0.0806(10) Uani 1 1 d . . .
H5 H 0.8135 0.6942 0.4788 0.097 Uiso 1 1 calc R . .
C1 C 1.1702(5) 0.7329(3) 0.8804(3) 0.1040(13) Uani 1 1 d . . .
H1A H 1.1697 0.7907 0.9055 0.156 Uiso 1 1 calc R . .
H1B H 1.2824 0.7101 0.8853 0.156 Uiso 1 1 calc R . .
H1C H 1.0968 0.6972 0.9165 0.156 Uiso 1 1 calc R . .
O1 O 0.9524(2) 0.77683(13) 0.77407(14) 0.0656(5) Uani 1 1 d . . .
C10 C 0.6866(3) 0.97172(16) 0.88648(16) 0.0457(6) Uani 1 1 d . . .
C11 C 1.0182(3) 0.98921(17) 0.79048(18) 0.0515(6) Uani 1 1 d . . .
H11 H 1.0300 0.9891 0.8570 0.062 Uiso 1 1 calc R . .
C12 C 1.1574(3) 1.01759(18) 0.73201(19) 0.0542(6) Uani 1 1 d . . .
C13 C 1.2988(4) 1.0540(2) 0.7750(2) 0.0660(8) Uani 1 1 d . . .
H13 H 1.3048 1.0620 0.8411 0.079 Uiso 1 1 calc R . .
C14 C 1.4324(4) 1.0789(2) 0.7204(3) 0.0835(10) Uani 1 1 d . . .
H14 H 1.5277 1.1037 0.7495 0.100 Uiso 1 1 calc R . .
C17 C 1.1503(4) 1.0062(3) 0.6336(2) 0.0874(11) Uani 1 1 d . . .
H17 H 1.0554 0.9817 0.6036 0.105 Uiso 1 1 calc R . .
C15 C 1.4230(5) 1.0669(3) 0.6238(3) 0.1017(13) Uani 1 1 d . . .
H15 H 1.5127 1.0834 0.5870 0.122 Uiso 1 1 calc R . .
C16 C 1.2838(5) 1.0311(4) 0.5803(3) 0.1155(16) Uani 1 1 d . . .
H16 H 1.2789 1.0235 0.5142 0.139 Uiso 1 1 calc R . .
H1 H 0.481(4) 0.929(2) 0.941(2) 0.068(9) Uiso 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N2 N1 114.7(2) . . ?
C10 N2 H1 125(2) . . ?
N1 N2 H1 120(2) . . ?
C10 N3 C9 108.47(19) . . ?
C10 N3 N4 130.3(2) . . ?
C9 N3 N4 119.87(18) . . ?
C11 N4 N3 117.0(2) . . ?
C9 N1 N2 103.64(19) . . ?
N1 C9 N3 110.8(2) . . ?
N1 C9 C8 126.8(2) . . ?
N3 C9 C8 122.3(2) . . ?
C7 C8 C3 119.7(2) . . ?
C7 C8 C9 120.4(2) . . ?
C3 C8 C9 119.9(2) . . ?
O1 C3 C8 115.3(2) . . ?
O1 C3 C4 125.3(3) . . ?
C8 C3 C4 119.4(3) . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
O1 C2 C1 107.7(3) . . ?
O1 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 O1 C2 119.4(2) . . ?
N2 C10 N3 102.4(2) . . ?
N2 C10 S1 128.58(18) . . ?
N3 C10 S1 129.03(18) . . ?
N4 C11 C12 119.2(2) . . ?
N4 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C17 119.2(3) . . ?
C13 C12 C11 120.1(3) . . ?
C17 C12 C11 120.7(3) . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C17 C12 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.4(4) . . ?
C15 C16 H16 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.682(3) . ?
N2 C10 1.330(3) . ?
N2 N1 1.370(3) . ?
N2 H1 0.85(3) . ?
N3 C10 1.374(3) . ?
N3 C9 1.376(3) . ?
N3 N4 1.399(3) . ?
N4 C11 1.251(3) . ?
N1 C9 1.294(3) . ?
C9 C8 1.468(3) . ?
C8 C7 1.385(4) . ?
C8 C3 1.391(4) . ?
C3 O1 1.353(3) . ?
C3 C4 1.391(4) . ?
C7 C6 1.380(4) . ?
C7 H7 0.9300 . ?
C4 C5 1.369(5) . ?
C4 H4 0.9300 . ?
C6 C5 1.364(5) . ?
C6 H6 0.9300 . ?
C2 O1 1.428(3) . ?
C2 C1 1.471(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 H5 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C11 C12 1.468(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(4) . ?
C12 C17 1.385(4) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(5) . ?
C14 H14 0.9300 . ?
C17 C16 1.375(4) . ?
C17 H17 0.9300 . ?
C15 C16 1.360(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653949
