##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
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##############################################################################
data_global
_audit_creation_method     'APEX2 v2014.11-0'
_journal_date_recd_electronic     2016-03-08
_journal_date_accepted     2016-03-16
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      3
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616004533
_journal_coeditor_code     RZ4002
_publ_contact_author_name
;
Mustafa R. Albayati
;
_publ_contact_author_address
;
Kirkuk University,
College of Science,
Department of Chemistry,
Kirkuk,
Iraq
;
_publ_contact_author_email     'shaabankamel@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
2-({5-[(4-Chlorophenoxy)methyl]-4-phenyl-4H-1,2,4-triazol-\
3-yl}sulfanyl)-N-phenylacetamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Joel T. Mague'
;
Department of Chemistry,
Tulane University,
New Orleans,
LA 70118,
USA
;
    'Mohamed, Shaaban K.'
;
Chemistry and Environmental Division,
Manchester Metropolitan University,
Manchester M1 5GD,
England
Chemistry Department,
Faculty of Science,
Minia University,
61519 El-Minia,
Egypt
;
    'Akkurt, Mehmet'
;
Department of Physics,
Faculty of Sciences,
Erciyes University,
38039 Kayseri,
Turkey
;
    'Etify A. Bakhite'
;
Chemistry Department,
Faculty of Science,
Assiut University,
Assiut 71516,
Egypt
;
    'Mustafa R. Albayati'
;
Kirkuk University,
College of Science,
Department of Chemistry,
Kirkuk,
Iraq
;
_publ_section_synopsis
;
In the crystal, the title molecule has an `extended' conformation.
Pairwise N---H...N and C---H...O hydrogen bonds form `stair-step'
chains.
;
data_I
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;\
2-({5-[(4-Chlorophenoxy)methyl]-4-phenyl-4H-1,2,4-triazol-\
3-yl}sulfanyl)-N-phenylacetamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H19 Cl N4 O2 S'
_chemical_formula_sum     'C23 H19 Cl N4 O2 S'
_chemical_formula_iupac     'C23 H19 Cl N4 O2 S'
_chemical_formula_weight     450.93
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'C 2/c'
_space_group_name_Hall     '-C 2yc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     15.7940(12)
_cell_length_b     11.1864(8)
_cell_length_c     24.8212(18)
_cell_angle_alpha     90
_cell_angle_beta     95.1280(10)
_cell_angle_gamma     90
_cell_volume     4367.8(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9935
_cell_measurement_theta_min     2.3407
_cell_measurement_theta_max     28.8656
_cell_measurement_temperature     150(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.240
_exptl_crystal_size_mid     0.200
_exptl_crystal_size_min     0.110
_exptl_crystal_density_diffrn     1.371
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1872
_exptl_absorpt_coefficient_mu     0.299
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_shelx_estimated_absorpt_T_min     0.932
_shelx_estimated_absorpt_T_max     0.968
_exptl_absorpt_correction_T_min     0.86
_exptl_absorpt_correction_T_max     0.97
_exptl_special_details
;
The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, colllected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 20 sec/frame.
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     41579
_diffrn_reflns_av_R_equivalents     0.0449
_diffrn_reflns_theta_min     1.647
_diffrn_reflns_theta_max     29.176
_diffrn_reflns_theta_full     29.100
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     34
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon
were placed in calculated positions (C---H = 0.95 - 0.99 Å) while that
attached to nitrogen was placed in a location derived from a difference
map and its coordinates adjusted to give N---H = 0.91 %A. All were included
as riding contributions with isotropic displacement parameters 1.2 times
those of the attached atoms. The 4-chlorophenyl group is disordered over
two orientations in a 95:5 ratio. The minor component was refined as a
rigid hexagon.
;
_reflns_number_total     5886
_reflns_number_gt     4471
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0605
_refine_ls_R_factor_gt     0.0431
_refine_ls_wR_factor_gt     0.1093
_refine_ls_wR_factor_ref     0.1177
_refine_ls_goodness_of_fit_ref     1.055
_refine_ls_restrained_S_all     1.055
_refine_ls_number_reflns     5886
_refine_ls_number_parameters     287
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0604P)²+1.3119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.410
_refine_diff_density_min     -0.215
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.58100(3) -0.46695(4) 0.30292(2) 0.06539(18) Uani d 1 . .
    S S1 0.33857(2) 0.45849(3) 0.39103(2) 0.02814(10) Uani d 1 . .
    O O1 0.50609(7) 0.00496(9) 0.38890(4) 0.0346(2) Uani d 1 . .
    O O2 0.26017(7) 0.68130(9) 0.39453(4) 0.0356(3) Uani d 1 . .
    N N1 0.53671(8) 0.27205(11) 0.44169(5) 0.0323(3) Uani d 1 . .
    N N2 0.48065(8) 0.36629(11) 0.44741(5) 0.0298(3) Uani d 1 . .
    N N3 0.43815(7) 0.26509(9) 0.37347(4) 0.0226(2) Uani d 1 . .
    N N4 0.33954(7) 0.76835(10) 0.46533(5) 0.0257(2) Uani d 1 . .
    H H4 0.3802 0.7527 0.4927 0.031 Uiso d 1 . .
    C C1 0.52663(12) -0.10073(13) 0.36507(7) 0.0287(4) Uani d 0.948(2) A 1
    C C2 0.60655(11) -0.12626(15) 0.35021(8) 0.0393(4) Uani d 0.948(2) A 1
    H H2 0.6499 -0.0672 0.3536 0.047 Uiso calc 0.948(2) A 1
    C C3 0.62341(12) -0.23890(16) 0.33017(8) 0.0452(5) Uani d 0.948(2) A 1
    H H3 0.6786 -0.2580 0.3204 0.054 Uiso calc 0.948(2) A 1
    C C4 0.55925(12) -0.32265(15) 0.32458(7) 0.0379(4) Uani d 0.948(2) A 1
    C C5 0.47874(12) -0.29637(15) 0.33764(8) 0.0410(4) Uani d 0.948(2) A 1
    H H5 0.4349 -0.3545 0.3328 0.049 Uiso calc 0.948(2) A 1
    C C6 0.46197(11) -0.18450(15) 0.35786(7) 0.0383(4) Uani d 0.948(2) A 1
    H H6 0.4063 -0.1651 0.3668 0.046 Uiso calc 0.948(2) A 1
    C C1A 0.5373(18) -0.1082(12) 0.3766(10) 0.0287(4) Uani d 0.052(2) A 2
    C C2A 0.5741(17) -0.1263(15) 0.3285(9) 0.0393(4) Uani d 0.052(2) A 2
    H H2A 0.5901 -0.0597 0.3079 0.047 Uiso calc 0.052(2) A 2
    C C3A 0.5875(17) -0.2418(19) 0.3104(8) 0.0452(5) Uani d 0.052(2) A 2
    H H3A 0.6126 -0.2542 0.2775 0.054 Uiso calc 0.052(2) A 2
    C C4A 0.5641(19) -0.3392(13) 0.3406(9) 0.0379(4) Uani d 0.052(2) A 2
    C C5A 0.5273(16) -0.3211(13) 0.3887(9) 0.0410(4) Uani d 0.052(2) A 2
    H H5A 0.5113 -0.3877 0.4093 0.049 Uiso calc 0.052(2) A 2
    C C6A 0.5139(15) -0.2056(16) 0.4068(8) 0.0383(4) Uani d 0.052(2) A 2
    H H6A 0.4887 -0.1932 0.4397 0.046 Uiso calc 0.052(2) A 2
    C C7 0.55380(9) 0.10811(12) 0.37635(6) 0.0300(3) Uani d 1 . .
    H H7A 0.5558 0.1153 0.3367 0.036 Uiso calc 1 . .
    H H7B 0.6128 0.1021 0.3934 0.036 Uiso calc 1 . .
    C C8 0.51050(9) 0.21362(12) 0.39776(6) 0.0262(3) Uani d 1 . .
    C C9 0.42313(8) 0.36036(11) 0.40612(5) 0.0238(3) Uani d 1 . .
    C C10 0.38827(8) 0.22517(12) 0.32540(5) 0.0226(3) Uani d 1 . .
    C C11 0.37983(10) 0.29843(13) 0.28040(6) 0.0327(3) Uani d 1 . .
    H H11 0.4063 0.3747 0.2811 0.039 Uiso calc 1 . .
    C C12 0.33191(11) 0.25847(14) 0.23410(6) 0.0386(4) Uani d 1 . .
    H H12 0.3247 0.3085 0.2031 0.046 Uiso calc 1 . .
    C C13 0.29497(10) 0.14698(14) 0.23290(6) 0.0349(3) Uani d 1 . .
    H H13 0.2630 0.1199 0.2010 0.042 Uiso calc 1 . .
    C C14 0.30446(10) 0.07439(14) 0.27815(6) 0.0339(3) Uani d 1 . .
    H H14 0.2793 -0.0028 0.2771 0.041 Uiso calc 1 . .
    C C15 0.35049(9) 0.11348(12) 0.32500(6) 0.0269(3) Uani d 1 . .
    H H15 0.3560 0.0644 0.3563 0.032 Uiso calc 1 . .
    C C16 0.36384(11) 0.56155(13) 0.44629(6) 0.0328(3) Uani d 1 . .
    H H16A 0.3468 0.5275 0.4805 0.039 Uiso calc 1 . .
    H H16B 0.4257 0.5776 0.4506 0.039 Uiso calc 1 . .
    C C17 0.31512(9) 0.67619(12) 0.43258(5) 0.0260(3) Uani d 1 . .
    C C18 0.31242(9) 0.88903(12) 0.46004(5) 0.0253(3) Uani d 1 . .
    C C19 0.36564(11) 0.97533(13) 0.48553(6) 0.0340(3) Uani d 1 . .
    H H19 0.4176 0.9520 0.5050 0.041 Uiso calc 1 . .
    C C20 0.34301(13) 1.09500(14) 0.48259(7) 0.0426(4) Uani d 1 . .
    H H20 0.3795 1.1534 0.5001 0.051 Uiso calc 1 . .
    C C21 0.26751(13) 1.12977(14) 0.45431(7) 0.0441(4) Uani d 1 . .
    H H21 0.2521 1.2118 0.4522 0.053 Uiso calc 1 . .
    C C22 0.21490(12) 1.04423(14) 0.42929(7) 0.0413(4) Uani d 1 . .
    H H22 0.1628 1.0680 0.4102 0.050 Uiso calc 1 . .
    C C23 0.23653(10) 0.92380(14) 0.43150(6) 0.0326(3) Uani d 1 . .
    H H23 0.2000 0.8659 0.4137 0.039 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C4A . 1.741(11) ?
    Cl1 C4 . 1.7452(16) ?
    S1 C9 . 1.7434(14) ?
    S1 C16 . 1.8089(14) ?
    O1 C1 . 1.3738(17) ?
    O1 C1A . 1.402(11) ?
    O1 C7 . 1.4277(18) ?
    O2 C17 . 1.2257(17) ?
    N1 C8 . 1.3065(18) ?
    N1 N2 . 1.3920(16) ?
    N2 C9 . 1.3092(17) ?
    N3 C8 . 1.3703(17) ?
    N3 C9 . 1.3724(16) ?
    N3 C10 . 1.4405(16) ?
    N4 C17 . 1.3477(17) ?
    N4 C18 . 1.4189(17) ?
    N4 H4 . 0.9098 ?
    C1 C2 . 1.376(2) ?
    C1 C6 . 1.386(2) ?
    C2 C3 . 1.389(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.378(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.372(3) ?
    C5 C6 . 1.383(2) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C1A C2A . 1.3900 ?
    C1A C6A . 1.3900 ?
    C2A C3A . 1.3900 ?
    C2A H2A . 0.9500 ?
    C3A C4A . 1.3900 ?
    C3A H3A . 0.9500 ?
    C4A C5A . 1.3900 ?
    C5A C6A . 1.3900 ?
    C5A H5A . 0.9500 ?
    C6A H6A . 0.9500 ?
    C7 C8 . 1.4861(19) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C10 C11 . 1.3822(19) ?
    C10 C15 . 1.3843(18) ?
    C11 C12 . 1.392(2) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.376(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.383(2) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.3858(19) ?
    C14 H14 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.5184(19) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C18 C23 . 1.392(2) ?
    C18 C19 . 1.394(2) ?
    C19 C20 . 1.386(2) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.384(3) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.378(3) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.390(2) ?
    C22 H22 . 0.9500 ?
    C23 H23 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C9 S1 C16 . . 97.21(6) ?
    C1 O1 C7 . . 116.88(12) ?
    C1A O1 C7 . . 118.7(10) ?
    C8 N1 N2 . . 107.88(11) ?
    C9 N2 N1 . . 106.56(11) ?
    C8 N3 C9 . . 104.34(11) ?
    C8 N3 C10 . . 127.37(11) ?
    C9 N3 C10 . . 128.26(11) ?
    C17 N4 C18 . . 127.18(12) ?
    C17 N4 H4 . . 116.6 ?
    C18 N4 H4 . . 116.1 ?
    O1 C1 C2 . . 123.47(16) ?
    O1 C1 C6 . . 115.96(15) ?
    C2 C1 C6 . . 120.54(14) ?
    C1 C2 C3 . . 119.60(17) ?
    C1 C2 H2 . . 120.2 ?
    C3 C2 H2 . . 120.2 ?
    C4 C3 C2 . . 119.34(16) ?
    C4 C3 H3 . . 120.3 ?
    C2 C3 H3 . . 120.3 ?
    C5 C4 C3 . . 121.28(15) ?
    C5 C4 Cl1 . . 118.89(15) ?
    C3 C4 Cl1 . . 119.78(14) ?
    C4 C5 C6 . . 119.43(16) ?
    C4 C5 H5 . . 120.3 ?
    C6 C5 H5 . . 120.3 ?
    C5 C6 C1 . . 119.73(16) ?
    C5 C6 H6 . . 120.1 ?
    C1 C6 H6 . . 120.1 ?
    C2A C1A C6A . . 120.0 ?
    C2A C1A O1 . . 120.0(14) ?
    C6A C1A O1 . . 118.4(14) ?
    C1A C2A C3A . . 120.0 ?
    C1A C2A H2A . . 120.0 ?
    C3A C2A H2A . . 120.0 ?
    C2A C3A C4A . . 120.0 ?
    C2A C3A H3A . . 120.0 ?
    C4A C3A H3A . . 120.0 ?
    C3A C4A C5A . . 120.0 ?
    C3A C4A Cl1 . . 107.1(13) ?
    C5A C4A Cl1 . . 132.6(13) ?
    C6A C5A C4A . . 120.0 ?
    C6A C5A H5A . . 120.0 ?
    C4A C5A H5A . . 120.0 ?
    C5A C6A C1A . . 120.0 ?
    C5A C6A H6A . . 120.0 ?
    C1A C6A H6A . . 120.0 ?
    O1 C7 C8 . . 107.16(12) ?
    O1 C7 H7A . . 110.3 ?
    C8 C7 H7A . . 110.3 ?
    O1 C7 H7B . . 110.3 ?
    C8 C7 H7B . . 110.3 ?
    H7A C7 H7B . . 108.5 ?
    N1 C8 N3 . . 110.29(12) ?
    N1 C8 C7 . . 125.05(13) ?
    N3 C8 C7 . . 124.65(12) ?
    N2 C9 N3 . . 110.93(12) ?
    N2 C9 S1 . . 126.94(10) ?
    N3 C9 S1 . . 122.12(10) ?
    C11 C10 C15 . . 121.26(12) ?
    C11 C10 N3 . . 119.45(12) ?
    C15 C10 N3 . . 119.29(12) ?
    C10 C11 C12 . . 118.87(13) ?
    C10 C11 H11 . . 120.6 ?
    C12 C11 H11 . . 120.6 ?
    C13 C12 C11 . . 120.47(14) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    C12 C13 C14 . . 119.96(14) ?
    C12 C13 H13 . . 120.0 ?
    C14 C13 H13 . . 120.0 ?
    C13 C14 C15 . . 120.45(14) ?
    C13 C14 H14 . . 119.8 ?
    C15 C14 H14 . . 119.8 ?
    C10 C15 C14 . . 118.97(13) ?
    C10 C15 H15 . . 120.5 ?
    C14 C15 H15 . . 120.5 ?
    C17 C16 S1 . . 107.17(10) ?
    C17 C16 H16A . . 110.3 ?
    S1 C16 H16A . . 110.3 ?
    C17 C16 H16B . . 110.3 ?
    S1 C16 H16B . . 110.3 ?
    H16A C16 H16B . . 108.5 ?
    O2 C17 N4 . . 125.02(12) ?
    O2 C17 C16 . . 121.46(12) ?
    N4 C17 C16 . . 113.51(12) ?
    C23 C18 C19 . . 119.62(13) ?
    C23 C18 N4 . . 123.51(13) ?
    C19 C18 N4 . . 116.87(13) ?
    C20 C19 C18 . . 120.19(15) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C21 C20 C19 . . 120.30(16) ?
    C21 C20 H20 . . 119.9 ?
    C19 C20 H20 . . 119.9 ?
    C22 C21 C20 . . 119.39(15) ?
    C22 C21 H21 . . 120.3 ?
    C20 C21 H21 . . 120.3 ?
    C21 C22 C23 . . 121.27(16) ?
    C21 C22 H22 . . 119.4 ?
    C23 C22 H22 . . 119.4 ?
    C22 C23 C18 . . 119.23(15) ?
    C22 C23 H23 . . 120.4 ?
    C18 C23 H23 . . 120.4 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C8 N1 N2 C9 . . . . -0.32(16) ?
    C7 O1 C1 C2 . . . . 28.4(2) ?
    C7 O1 C1 C6 . . . . -153.50(14) ?
    O1 C1 C2 C3 . . . . 175.06(16) ?
    C6 C1 C2 C3 . . . . -3.0(3) ?
    C1 C2 C3 C4 . . . . 1.2(3) ?
    C2 C3 C4 C5 . . . . 1.0(3) ?
    C2 C3 C4 Cl1 . . . . -176.55(15) ?
    C3 C4 C5 C6 . . . . -1.3(3) ?
    Cl1 C4 C5 C6 . . . . 176.23(14) ?
    C4 C5 C6 C1 . . . . -0.5(3) ?
    O1 C1 C6 C5 . . . . -175.53(16) ?
    C2 C1 C6 C5 . . . . 2.7(3) ?
    C7 O1 C1A C2A . . . . -40.3(19) ?
    C7 O1 C1A C6A . . . . 154.0(11) ?
    C6A C1A C2A C3A . . . . 0.0 ?
    O1 C1A C2A C3A . . . . -166(2) ?
    C1A C2A C3A C4A . . . . 0.0 ?
    C2A C3A C4A C5A . . . . 0.0 ?
    C2A C3A C4A Cl1 . . . . 175(2) ?
    C3A C4A C5A C6A . . . . 0.0 ?
    Cl1 C4A C5A C6A . . . . -173(3) ?
    C4A C5A C6A C1A . . . . 0.0 ?
    C2A C1A C6A C5A . . . . 0.0 ?
    O1 C1A C6A C5A . . . . 166(2) ?
    C1 O1 C7 C8 . . . . 169.54(13) ?
    C1A O1 C7 C8 . . . . -175.2(13) ?
    N2 N1 C8 N3 . . . . -0.15(16) ?
    N2 N1 C8 C7 . . . . 178.55(13) ?
    C9 N3 C8 N1 . . . . 0.54(16) ?
    C10 N3 C8 N1 . . . . -177.78(13) ?
    C9 N3 C8 C7 . . . . -178.17(13) ?
    C10 N3 C8 C7 . . . . 3.5(2) ?
    O1 C7 C8 N1 . . . . 103.81(16) ?
    O1 C7 C8 N3 . . . . -77.67(17) ?
    N1 N2 C9 N3 . . . . 0.68(16) ?
    N1 N2 C9 S1 . . . . -177.94(11) ?
    C8 N3 C9 N2 . . . . -0.75(15) ?
    C10 N3 C9 N2 . . . . 177.55(12) ?
    C8 N3 C9 S1 . . . . 177.94(10) ?
    C10 N3 C9 S1 . . . . -3.76(19) ?
    C16 S1 C9 N2 . . . . 2.70(15) ?
    C16 S1 C9 N3 . . . . -175.77(12) ?
    C8 N3 C10 C11 . . . . -117.80(16) ?
    C9 N3 C10 C11 . . . . 64.27(19) ?
    C8 N3 C10 C15 . . . . 61.47(18) ?
    C9 N3 C10 C15 . . . . -116.46(15) ?
    C15 C10 C11 C12 . . . . 0.3(2) ?
    N3 C10 C11 C12 . . . . 179.60(13) ?
    C10 C11 C12 C13 . . . . -1.2(2) ?
    C11 C12 C13 C14 . . . . 0.8(2) ?
    C12 C13 C14 C15 . . . . 0.5(2) ?
    C11 C10 C15 C14 . . . . 0.9(2) ?
    N3 C10 C15 C14 . . . . -178.32(13) ?
    C13 C14 C15 C10 . . . . -1.4(2) ?
    C9 S1 C16 C17 . . . . 162.90(11) ?
    C18 N4 C17 O2 . . . . -5.4(2) ?
    C18 N4 C17 C16 . . . . 173.55(13) ?
    S1 C16 C17 O2 . . . . 10.32(18) ?
    S1 C16 C17 N4 . . . . -168.65(10) ?
    C17 N4 C18 C23 . . . . 22.5(2) ?
    C17 N4 C18 C19 . . . . -157.94(14) ?
    C23 C18 C19 C20 . . . . 0.2(2) ?
    N4 C18 C19 C20 . . . . -179.40(14) ?
    C18 C19 C20 C21 . . . . -0.1(2) ?
    C19 C20 C21 C22 . . . . 0.3(3) ?
    C20 C21 C22 C23 . . . . -0.6(3) ?
    C21 C22 C23 C18 . . . . 0.7(2) ?
    C19 C18 C23 C22 . . . . -0.5(2) ?
    N4 C18 C23 C22 . . . . 179.06(14) ?
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
    N4 H4 N1 5_666 0.91 2.02 2.9230(17) 174
    C7 H7B O2 3_545 0.99 2.49 3.3518(18) 146
    C3 H3 Cg3 5_545 0.95 2.92 3.867(2) 174
    C15 H15 Cg4 1_545 0.95 2.86 3.6871(16) 146
    C16 H16A Cg4 7_566 0.99 2.80 3.6488(18) 144
