#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/95/2239516.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_2239516
loop_
_publ_author_name
'Ben Othman, Raja'
'Marchivie, Mathieu'
'Suzenet, Franck'
'Routier, Sylvain'
_publ_section_title
;
 3-[(4-Phenoxyphenyl)sulfanyl]-5-phenyl-1H-1,2,4-triazole
;
_journal_coeditor_code           SU2718
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o622
_journal_page_last               o623
_journal_paper_doi               10.1107/S1600536814008204
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C20 H15 N3 O1 S'
_chemical_formula_moiety         'C20 H15 N3 O1 S'
_chemical_formula_sum            'C20 H15 N3 O S'
_chemical_formula_weight         345.41
_chemical_name_systematic
;
3-[(4-Phenoxyphenyl)sulfanyl]-5-phenyl-1H-1,2,4-triazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.12 svn.r2908 for OlexSys, GUI svn.r4796)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.131(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6112(12)
_cell_length_b                   5.8445(5)
_cell_length_c                   17.5415(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1700.5(2)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg, 1992)'
_computing_data_collection       'COLLECT (Bruker--Nonius, 1998)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'profile data from φ scans and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44120
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.290
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0707P)²+1.0533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1521
_reflns_number_gt                2333
_reflns_number_total             3099
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2718sup1.cif
_cod_data_source_block           I
_cod_database_code               2239516
_cod_database_fobs_code          2239516
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.932
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_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_occupancy
S S1 0.74490(4) 0.10572(13) 0.07643(5) 0.0708(3) Uani d 1
N N3 0.69265(12) 0.6140(4) 0.19811(11) 0.0507(5) Uani d 1
N N2 0.74402(12) 0.4385(4) 0.18506(11) 0.0540(5) Uani d 1
N N1 0.64442(12) 0.4567(4) 0.09308(11) 0.0539(5) Uani d 1
C C7 0.63379(13) 0.6216(4) 0.14328(13) 0.0474(5) Uani d 1
C C6 0.56826(8) 0.7865(3) 0.13936(9) 0.0518(6) Uani d 1
C C1 0.56878(10) 0.9796(3) 0.18563(10) 0.0661(7) Uani d 1
H H1 0.6109 1.0031 0.2219 0.079 Uiso calc 1
C C2 0.50635(12) 1.1377(3) 0.17765(12) 0.0811(9) Uani d 1
H H2 0.5067 1.2669 0.2086 0.097 Uiso calc 1
C C3 0.44340(10) 1.1026(4) 0.12341(13) 0.0885(11) Uani d 1
H H3A 0.4016 1.2083 0.1181 0.106 Uiso calc 1
C C4 0.44288(9) 0.9094(4) 0.07715(11) 0.0903(11) Uani d 1
H H4 0.4008 0.8859 0.0409 0.108 Uiso calc 1
C C5 0.50531(11) 0.7514(3) 0.08512(10) 0.0746(8) Uani d 1
H H5 0.5050 0.6222 0.0542 0.090 Uiso calc 1
C C9 0.85042(16) 0.1109(4) 0.09473(14) 0.0575(6) Uani d 1
C C12 1.01532(19) 0.0906(5) 0.1147(2) 0.0795(9) Uani d 1
C C8 0.71159(14) 0.3513(4) 0.12111(13) 0.0508(6) Uani d 1
C C14 0.89725(16) 0.2919(5) 0.07283(17) 0.0676(7) Uani d 1
H H14 0.8728 0.4205 0.0506 0.081 Uiso calc 1
C C13 0.97963(17) 0.2836(5) 0.08361(19) 0.0751(8) Uani d 1
H H13 1.0110 0.4074 0.0700 0.090 Uiso calc 1
C C10 0.8872(2) -0.0810(5) 0.12533(18) 0.0750(8) Uani d 1
H H10 0.8562 -0.2039 0.1403 0.090 Uiso calc 1
C C15 1.14533(12) 0.2518(3) 0.13117(13) 0.0779(9) Uani d 1
C C16 1.20579(14) 0.2829(4) 0.08041(11) 0.0981(13) Uani d 1
H H16 1.2114 0.1797 0.0407 0.118 Uiso calc 1
C C17 1.25792(12) 0.4683(5) 0.08903(12) 0.0986(12) Uani d 1
H H17 1.2984 0.4891 0.0551 0.118 Uiso calc 1
C C18 1.24959(12) 0.6225(4) 0.14841(16) 0.0937(11) Uani d 1
H H18 1.2845 0.7465 0.1542 0.112 Uiso calc 1
C C19 1.18913(14) 0.5914(3) 0.19916(12) 0.0873(10) Uani d 1
H H19 1.1836 0.6945 0.2389 0.105 Uiso calc 1
C C20 1.13700(11) 0.4060(4) 0.19055(12) 0.0786(9) Uani d 1
H H20 1.0966 0.3852 0.2245 0.094 Uiso calc 1
C C11 0.9694(2) -0.0913(5) 0.1338(2) 0.0885(10) Uani d 1
H H11 0.9941 -0.2238 0.1527 0.106 Uiso calc 1
H H3 0.7060(16) 0.717(5) 0.2355(16) 0.070(8) Uiso d 1
O O1 1.09730(15) 0.0639(4) 0.1246(2) 0.1279(16) Uani d 0.997(9)
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
C8 S1 C9 103.95(12)
N2 N3 H3 119.3(18)
C7 N3 N2 110.2(2)
C7 N3 H3 129.7(18)
C8 N2 N3 101.72(19)
C7 N1 C8 103.21(19)
N3 C7 C6 125.0(2)
N1 C7 N3 109.6(2)
N1 C7 C6 125.33(19)
C1 C6 C7 122.03(14)
C1 C6 C5 120.0
C5 C6 C7 117.92(14)
C6 C1 H1 120.0
C2 C1 C6 120.0
C2 C1 H1 120.0
C1 C2 H2 120.0
C3 C2 C1 120.0
C3 C2 H2 120.0
C2 C3 H3A 120.0
C2 C3 C4 120.0
C4 C3 H3A 120.0
C3 C4 H4 120.0
C3 C4 C5 120.0
C5 C4 H4 120.0
C6 C5 H5 120.0
C4 C5 C6 120.0
C4 C5 H5 120.0
C14 C9 S1 122.1(2)
C10 C9 S1 118.3(2)
C10 C9 C14 119.3(3)
C11 C12 C13 120.2(3)
C11 C12 O1 116.5(3)
O1 C12 C13 123.2(3)
N2 C8 S1 125.17(19)
N2 C8 N1 115.2(2)
N1 C8 S1 119.43(18)
C9 C14 H14 119.7
C13 C14 C9 120.5(3)
C13 C14 H14 119.7
C12 C13 H13 120.4
C14 C13 C12 119.3(3)
C14 C13 H13 120.4
C9 C10 H10 120.0
C11 C10 C9 120.0(3)
C11 C10 H10 120.0
C16 C15 C20 120.0
O1 C15 C16 119.5(2)
O1 C15 C20 120.4(2)
C15 C16 H16 120.0
C15 C16 C17 120.0
C17 C16 H16 120.0
C16 C17 H17 120.0
C18 C17 C16 120.0
C18 C17 H17 120.0
C17 C18 H18 120.0
C19 C18 C17 120.0
C19 C18 H18 120.0
C18 C19 H19 120.0
C18 C19 C20 120.0
C20 C19 H19 120.0
C15 C20 H20 120.0
C19 C20 C15 120.0
C19 C20 H20 120.0
C12 C11 C10 120.6(3)
C12 C11 H11 119.7
C10 C11 H11 119.7
C15 O1 C12 119.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.765(3)
S1 C8 1.740(3)
N3 N2 1.362(3)
N3 C7 1.334(3)
N3 H3 0.91(3)
N2 C8 1.320(3)
N1 C7 1.324(3)
N1 C8 1.344(3)
C7 C6 1.453(3)
C6 C1 1.3900
C6 C5 1.3900
C1 H1 0.9300
C1 C2 1.3900
C2 H2 0.9300
C2 C3 1.3900
C3 H3A 0.9300
C3 C4 1.3900
C4 H4 0.9300
C4 C5 1.3900
C5 H5 0.9300
C9 C14 1.380(4)
C9 C10 1.372(4)
C12 C13 1.374(4)
C12 C11 1.361(5)
C12 O1 1.372(4)
C14 H14 0.9300
C14 C13 1.372(4)
C13 H13 0.9300
C10 H10 0.9300
C10 C11 1.366(5)
C15 C16 1.3900
C15 C20 1.3900
C15 O1 1.359(3)
C16 H16 0.9300
C16 C17 1.3900
C17 H17 0.9300
C17 C18 1.3900
C18 H18 0.9300
C18 C19 1.3900
C19 H19 0.9300
C19 C20 1.3900
C20 H20 0.9300
C11 H11 0.9300
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
N3 H3 N2 2_655 0.91(3) 2.05(3) 2.944(3) 170(2) yes
C16 H16 S1 3_755 0.93 2.77 3.694(2) 170 yes
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
S1 C9 C14 C13 -175.8(2)
S1 C9 C10 C11 174.0(3)
N3 N2 C8 S1 -175.31(18)
N3 N2 C8 N1 -0.1(3)
N3 C7 C6 C1 12.0(3)
N3 C7 C6 C5 -170.67(19)
N2 N3 C7 N1 -0.5(3)
N2 N3 C7 C6 179.66(19)
N1 C7 C6 C1 -167.84(18)
N1 C7 C6 C5 9.5(3)
C7 N3 N2 C8 0.4(2)
C7 N1 C8 S1 175.31(17)
C7 N1 C8 N2 -0.2(3)
C7 C6 C1 C2 177.32(18)
C7 C6 C5 C4 -177.43(17)
C6 C1 C2 C3 0.0
C1 C6 C5 C4 0.0
C1 C2 C3 C4 0.0
C2 C3 C4 C5 0.0
C3 C4 C5 C6 0.0
C5 C6 C1 C2 0.0
C9 S1 C8 N2 -34.3(2)
C9 S1 C8 N1 150.7(2)
C9 C14 C13 C12 1.6(5)
C9 C10 C11 C12 2.4(5)
C8 S1 C9 C14 -57.9(3)
C8 S1 C9 C10 128.3(2)
C8 N1 C7 N3 0.4(3)
C8 N1 C7 C6 -179.7(2)
C14 C9 C10 C11 0.0(5)
C13 C12 C11 C10 -2.8(6)
C13 C12 O1 C15 24.8(5)
C10 C9 C14 C13 -2.0(4)
C15 C16 C17 C18 0.0
C16 C15 C20 C19 0.0
C16 C15 O1 C12 -122.6(3)
C16 C17 C18 C19 0.0
C17 C18 C19 C20 0.0
C18 C19 C20 C15 0.0
C20 C15 C16 C17 0.0
C20 C15 O1 C12 60.7(4)
C11 C12 C13 C14 0.8(5)
C11 C12 O1 C15 -158.7(3)
O1 C12 C13 C14 177.2(3)
O1 C12 C11 C10 -179.5(3)
O1 C15 C16 C17 -176.7(2)
O1 C15 C20 C19 176.7(2)
