##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#                                                                            #
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##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-06-16
_journal_date_accepted     2007-07-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      8
_journal_page_first     o3509
_journal_page_last     o3509
_journal_paper_category     QO
_journal_coeditor_code     OM2139
_publ_contact_author_name     'Dr. Chen-jiang Liu'
_publ_contact_author_address
;
Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education,
School of Chemistry and Chemical Engineering, Xinjiang University,
Urumqi 830046, P.R. China;
School of Sciences , Xi'an Jiaotong University ,
Xian 710049 , P.R. China
;
_publ_contact_author_email     pxylcj@126.com
_publ_contact_author_fax     '+86-991-8582807'
_publ_contact_author_phone     '+86-991-8581211'
_publ_section_title
;
5-(3-Methyl-5-phenoxy-1-phenylpyrazol-4-yl)-1,3,4-thiadiazol-2-amine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yan-Rong Sun' .
;
Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education,
School of Chemistry and Chemical Engineering, Xinjiang University,
Urumqi 830046, People's Republic of China
;
    'Gang Liu' .
;
Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education,
School of Chemistry and Chemical Engineering, Xinjiang University,
Urumqi 830046, People's Republic of China
;
    'Chen-Jiang Liu' .
;
Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education,
School of Chemistry and Chemical Engineering, Xinjiang University,
Urumqi 830046, People's Republic of China
and
School of Sciences, Xi'an Jiaotong University,
Xian 710049, People's Republic of China
;
    'Ji-De Wang' .
;
Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education,
School of Chemistry and Chemical Engineering, Xinjiang University,
Urumqi 830046, People's Republic of China
and
School of Sciences, Xi'an Jiaotong University,
Xian 710049, People's Republic of China
;
data_I
_chemical_name_systematic
;
5-(3-Methyl-5-phenoxy-1-phenylpyrazol-4-yl)-1,3,4-thiadiazol-2-amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H15 N5 O S'
_chemical_formula_sum     'C18 H15 N5 O S'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C18 H15 N5 O S'
_chemical_formula_weight     349.41
_chemical_melting_point     498
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     ?
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'
_cell_length_a     20.2987(5)
_cell_length_b     9.6934(3)
_cell_length_c     19.0726(6)
_cell_angle_alpha     90.00
_cell_angle_beta     114.8460(10)
_cell_angle_gamma     90.00
_cell_volume     3405.43(17)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     26663
_cell_measurement_theta_min     3.00
_cell_measurement_theta_max     27.49
_cell_measurement_temperature     153(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.66
_exptl_crystal_size_mid     0.43
_exptl_crystal_size_min     0.31
_exptl_crystal_density_diffrn     1.363
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1456
_exptl_absorpt_coefficient_mu     0.206
_exptl_absorpt_correction_type     empirical
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.8758
_exptl_absorpt_correction_T_max     0.9388
_exptl_special_details
;
;
_diffrn_ambient_temperature     153(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku R-AXIS SPIDER'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     32693
_diffrn_reflns_av_R_equivalents     0.0197
_diffrn_reflns_av_sigmaI/netI     0.0174
_diffrn_reflns_theta_min     3.00
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     26
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     23
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_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.
;
_reflns_number_total     7772
_reflns_number_gt     6769
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0412
_refine_ls_R_factor_gt     0.0358
_refine_ls_wR_factor_gt     0.0976
_refine_ls_wR_factor_ref     0.1009
_refine_ls_goodness_of_fit_ref     1.052
_refine_ls_restrained_S_all     1.052
_refine_ls_number_reflns     7772
_refine_ls_number_parameters     453
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0577P)²+0.8824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.242
_refine_diff_density_min     -0.410
_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'
_computing_data_collection     'RAPID-AUTO (Rigaku, 2004)'
_computing_cell_refinement     RAPID-AUTO
_computing_data_reduction     RAPID-AUTO
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3(Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.430303(16) 0.79622(3) 0.268570(16) 0.02420(8) Uani d . 1 . .
    S S2 0.053694(17) 0.72302(4) 0.263009(18) 0.03485(10) Uani d . 1 . .
    O O1 0.52710(4) 0.88205(9) 0.18168(5) 0.02343(18) Uani d . 1 . .
    O O2 -0.04172(5) 0.82952(9) 0.34655(5) 0.02735(19) Uani d . 1 . .
    N N1 0.33984(6) 0.79945(13) 0.34137(6) 0.0323(3) Uani d . 1 . .
    H H1A 0.2967 0.7916 0.3416 0.039 Uiso calc R 1 . .
    H H1B 0.3779 0.8193 0.3844 0.039 Uiso calc R 1 . .
    N N2 0.29285(6) 0.75129(12) 0.20940(6) 0.0250(2) Uani d . 1 . .
    N N3 0.31332(5) 0.73761(11) 0.14935(6) 0.0236(2) Uani d . 1 . .
    N N4 0.43532(5) 0.68631(11) 0.01202(6) 0.0234(2) Uani d . 1 . .
    N N5 0.49192(5) 0.76583(11) 0.06123(6) 0.0225(2) Uani d . 1 . .
    N N6 0.14095(6) 0.71887(15) 0.18704(7) 0.0384(3) Uani d . 1 . .
    H H6A 0.1835 0.7101 0.1857 0.046 Uiso calc R 1 . .
    H H6B 0.1017 0.7308 0.1439 0.046 Uiso calc R 1 . .
    N N7 0.19232(6) 0.69641(13) 0.32166(6) 0.0295(2) Uani d . 1 . .
    N N8 0.17298(6) 0.68692(12) 0.38289(6) 0.0285(2) Uani d . 1 . .
    N N9 0.05654(5) 0.67127(12) 0.52749(6) 0.0269(2) Uani d . 1 . .
    N N10 -0.00125(5) 0.74338(12) 0.47454(6) 0.0249(2) Uani d . 1 . .
    C C1 0.58095(6) 0.93578(13) 0.06074(7) 0.0267(3) Uani d . 1 . .
    H H1C 0.5691 0.9941 0.0938 0.032 Uiso calc R 1 . .
    C C2 0.63228(7) 0.97676(15) 0.03447(8) 0.0316(3) Uani d . 1 . .
    H H2B 0.6565 1.0627 0.0506 0.038 Uiso calc R 1 . .
    C C3 0.64825(8) 0.89297(16) -0.01502(9) 0.0380(3) Uani d . 1 . .
    H H3B 0.6829 0.9219 -0.0333 0.046 Uiso calc R 1 . .
    C C4 0.61364(9) 0.76660(17) -0.03796(10) 0.0414(3) Uani d . 1 . .
    H H4B 0.6242 0.7099 -0.0726 0.050 Uiso calc R 1 . .
    C C5 0.56374(8) 0.72254(15) -0.01070(8) 0.0334(3) Uani d . 1 . .
    H H5A 0.5412 0.6348 -0.0251 0.040 Uiso calc R 1 . .
    C C6 0.54718(6) 0.80857(13) 0.03806(7) 0.0235(2) Uani d . 1 . .
    C C7 0.32015(7) 0.59679(14) 0.00612(7) 0.0283(3) Uani d . 1 . .
    H H7B 0.3224 0.5393 -0.0351 0.042 Uiso calc R 1 . .
    H H7C 0.2798 0.6622 -0.0161 0.042 Uiso calc R 1 . .
    H H7D 0.3126 0.5380 0.0439 0.042 Uiso calc R 1 . .
    C C8 0.38972(6) 0.67421(12) 0.04516(6) 0.0218(2) Uani d . 1 . .
    C C9 0.41636(6) 0.74462(12) 0.11713(6) 0.0212(2) Uani d . 1 . .
    C C10 0.48134(6) 0.80017(12) 0.12464(6) 0.0209(2) Uani d . 1 . .
    C C11 0.59244(6) 0.82460(12) 0.23525(6) 0.0206(2) Uani d . 1 . .
    C C12 0.60255(7) 0.68515(13) 0.25028(8) 0.0289(3) Uani d . 1 . .
    H H12A 0.5653 0.6208 0.2227 0.035 Uiso calc R 1 . .
    C C13 0.66881(8) 0.64136(15) 0.30706(8) 0.0342(3) Uani d . 1 . .
    H H13A 0.6770 0.5457 0.3182 0.041 Uiso calc R 1 . .
    C C14 0.72283(7) 0.73517(15) 0.34745(8) 0.0324(3) Uani d . 1 . .
    H H14A 0.7677 0.7042 0.3864 0.039 Uiso calc R 1 . .
    C C15 0.71116(7) 0.87414(15) 0.33085(8) 0.0334(3) Uani d . 1 . .
    H H15A 0.7482 0.9389 0.3583 0.040 Uiso calc R 1 . .
    C C16 0.64566(7) 0.91945(13) 0.27442(7) 0.0288(3) Uani d . 1 . .
    H H16A 0.6376 1.0150 0.2629 0.035 Uiso calc R 1 . .
    C C17 0.38236(6) 0.75766(12) 0.17010(6) 0.0208(2) Uani d . 1 . .
    C C18 0.34753(7) 0.78104(12) 0.27530(7) 0.0236(2) Uani d . 1 . .
    C C19 -0.08683(7) 0.92639(14) 0.46842(8) 0.0306(3) Uani d . 1 . .
    H H19A -0.0778 0.9722 0.4293 0.037 Uiso calc R 1 . .
    C C20 -0.13382(7) 0.98335(16) 0.49647(8) 0.0371(3) Uani d . 1 . .
    H H20A -0.1574 1.0683 0.4760 0.044 Uiso calc R 1 . .
    C C21 -0.14653(8) 0.9176(2) 0.55371(9) 0.0460(4) Uani d . 1 . .
    H H21A -0.1782 0.9578 0.5731 0.055 Uiso calc R 1 . .
    C C22 -0.11300(8) 0.7928(2) 0.58291(9) 0.0484(4) Uani d . 1 . .
    H H22A -0.1219 0.7475 0.6223 0.058 Uiso calc R 1 . .
    C C23 -0.06649(7) 0.73330(17) 0.55515(8) 0.0360(3) Uani d . 1 . .
    H H23A -0.0440 0.6471 0.5747 0.043 Uiso calc R 1 . .
    C C24 -0.05322(6) 0.80151(14) 0.49835(7) 0.0261(3) Uani d . 1 . .
    C C25 0.16923(7) 0.56799(15) 0.53478(8) 0.0318(3) Uani d . 1 . .
    H H25A 0.1701 0.5290 0.5826 0.048 Uiso calc R 1 . .
    H H25B 0.2101 0.6317 0.5473 0.048 Uiso calc R 1 . .
    H H25C 0.1731 0.4934 0.5020 0.048 Uiso calc R 1 . .
    C C26 0.09973(6) 0.64382(13) 0.49282(7) 0.0248(2) Uani d . 1 . .
    C C27 0.07052(6) 0.69711(13) 0.41642(7) 0.0238(2) Uani d . 1 . .
    C C28 0.00615(6) 0.75820(13) 0.40755(7) 0.0238(2) Uani d . 1 . .
    C C29 -0.10629(6) 0.76360(14) 0.29741(7) 0.0249(2) Uani d . 1 . .
    C C30 -0.11821(7) 0.62435(15) 0.29970(9) 0.0356(3) Uani d . 1 . .
    H H30A -0.0826 0.5666 0.3365 0.043 Uiso calc R 1 . .
    C C31 -0.18401(9) 0.57004(19) 0.24642(10) 0.0491(4) Uani d . 1 . .
    H H31A -0.1932 0.4741 0.2471 0.059 Uiso calc R 1 . .
    C C32 -0.23534(8) 0.6529(2) 0.19326(9) 0.0497(4) Uani d . 1 . .
    H H32A -0.2797 0.6145 0.1571 0.060 Uiso calc R 1 . .
    C C33 -0.22249(8) 0.7914(2) 0.19243(9) 0.0504(5) Uani d . 1 . .
    H H33A -0.2583 0.8489 0.1557 0.061 Uiso calc R 1 . .
    C C34 -0.15764(8) 0.84882(17) 0.24470(8) 0.0378(3) Uani d . 1 . .
    H H34A -0.1489 0.9450 0.2441 0.045 Uiso calc R 1 . .
    C C35 0.10357(6) 0.69930(13) 0.36219(7) 0.0242(2) Uani d . 1 . .
    C C36 0.13585(7) 0.71394(14) 0.25529(7) 0.0280(3) Uani d . 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
    S1 C18 . 1.7442(12) ?
    S1 C17 . 1.7545(12) ?
    S2 C36 . 1.7370(13) ?
    S2 C35 . 1.7454(12) ?
    O1 C10 . 1.3517(14) ?
    O1 C11 . 1.4050(14) ?
    O2 C28 . 1.3512(15) ?
    O2 C29 . 1.4043(15) ?
    N1 C18 . 1.3452(15) ?
    N1 H1A . 0.8800 ?
    N1 H1B . 0.8800 ?
    N2 C18 . 1.3124(16) ?
    N2 N3 . 1.3791(13) ?
    N3 C17 . 1.3007(15) ?
    N4 C8 . 1.3272(15) ?
    N4 N5 . 1.3743(14) ?
    N5 C10 . 1.3556(15) ?
    N5 C6 . 1.4288(15) ?
    N6 C36 . 1.3493(17) ?
    N6 H6A . 0.8800 ?
    N6 H6B . 0.8800 ?
    N7 C36 . 1.3136(17) ?
    N7 N8 . 1.3826(14) ?
    N8 C35 . 1.2991(16) ?
    N9 C26 . 1.3279(16) ?
    N9 N10 . 1.3744(14) ?
    N10 C28 . 1.3555(15) ?
    N10 C24 . 1.4279(15) ?
    C1 C6 . 1.3887(18) ?
    C1 C2 . 1.3904(17) ?
    C1 H1C . 0.9500 ?
    C2 C3 . 1.383(2) ?
    C2 H2B . 0.9500 ?
    C3 C4 . 1.388(2) ?
    C3 H3B . 0.9500 ?
    C4 C5 . 1.3859(19) ?
    C4 H4B . 0.9500 ?
    C5 C6 . 1.3915(18) ?
    C5 H5A . 0.9500 ?
    C7 C8 . 1.4927(16) ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
    C7 H7D . 0.9800 ?
    C8 C9 . 1.4207(16) ?
    C9 C10 . 1.3755(16) ?
    C9 C17 . 1.4488(15) ?
    C11 C16 . 1.3757(17) ?
    C11 C12 . 1.3791(17) ?
    C12 C13 . 1.3922(18) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.383(2) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.381(2) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.3844(18) ?
    C15 H15A . 0.9500 ?
    C16 H16A . 0.9500 ?
    C19 C20 . 1.3892(18) ?
    C19 C24 . 1.3891(19) ?
    C19 H19A . 0.9500 ?
    C20 C21 . 1.379(2) ?
    C20 H20A . 0.9500 ?
    C21 C22 . 1.385(3) ?
    C21 H21A . 0.9500 ?
    C22 C23 . 1.387(2) ?
    C22 H22A . 0.9500 ?
    C23 C24 . 1.3888(19) ?
    C23 H23A . 0.9500 ?
    C25 C26 . 1.4908(17) ?
    C25 H25A . 0.9800 ?
    C25 H25B . 0.9800 ?
    C25 H25C . 0.9800 ?
    C26 C27 . 1.4198(17) ?
    C27 C28 . 1.3787(17) ?
    C27 C35 . 1.4503(16) ?
    C29 C30 . 1.375(2) ?
    C29 C34 . 1.3781(18) ?
    C30 C31 . 1.398(2) ?
    C30 H30A . 0.9500 ?
    C31 C32 . 1.368(3) ?
    C31 H31A . 0.9500 ?
    C32 C33 . 1.369(3) ?
    C32 H32A . 0.9500 ?
    C33 C34 . 1.391(2) ?
    C33 H33A . 0.9500 ?
    C34 H34A . 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
    C18 S1 C17 . . 86.71(5) ?
    C36 S2 C35 . . 86.84(6) ?
    C10 O1 C11 . . 118.17(9) ?
    C28 O2 C29 . . 118.28(10) ?
    C18 N1 H1A . . 120.0 ?
    C18 N1 H1B . . 120.0 ?
    H1A N1 H1B . . 120.0 ?
    C18 N2 N3 . . 112.82(10) ?
    C17 N3 N2 . . 113.26(10) ?
    C8 N4 N5 . . 105.94(9) ?
    C10 N5 N4 . . 110.28(9) ?
    C10 N5 C6 . . 130.08(10) ?
    N4 N5 C6 . . 119.42(9) ?
    C36 N6 H6A . . 120.0 ?
    C36 N6 H6B . . 120.0 ?
    H6A N6 H6B . . 120.0 ?
    C36 N7 N8 . . 112.34(10) ?
    C35 N8 N7 . . 113.19(10) ?
    C26 N9 N10 . . 105.92(10) ?
    C28 N10 N9 . . 110.37(10) ?
    C28 N10 C24 . . 130.33(11) ?
    N9 N10 C24 . . 118.92(10) ?
    C6 C1 C2 . . 119.22(12) ?
    C6 C1 H1C . . 120.4 ?
    C2 C1 H1C . . 120.4 ?
    C3 C2 C1 . . 120.27(13) ?
    C3 C2 H2B . . 119.9 ?
    C1 C2 H2B . . 119.9 ?
    C2 C3 C4 . . 120.04(12) ?
    C2 C3 H3B . . 120.0 ?
    C4 C3 H3B . . 120.0 ?
    C5 C4 C3 . . 120.43(14) ?
    C5 C4 H4B . . 119.8 ?
    C3 C4 H4B . . 119.8 ?
    C4 C5 C6 . . 119.08(13) ?
    C4 C5 H5A . . 120.5 ?
    C6 C5 H5A . . 120.5 ?
    C1 C6 C5 . . 120.93(11) ?
    C1 C6 N5 . . 120.67(11) ?
    C5 C6 N5 . . 118.33(11) ?
    C8 C7 H7B . . 109.5 ?
    C8 C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C8 C7 H7D . . 109.5 ?
    H7B C7 H7D . . 109.5 ?
    H7C C7 H7D . . 109.5 ?
    N4 C8 C9 . . 111.05(10) ?
    N4 C8 C7 . . 120.65(10) ?
    C9 C8 C7 . . 128.29(10) ?
    C10 C9 C8 . . 104.34(10) ?
    C10 C9 C17 . . 127.61(11) ?
    C8 C9 C17 . . 128.04(11) ?
    O1 C10 N5 . . 123.32(10) ?
    O1 C10 C9 . . 128.20(10) ?
    N5 C10 C9 . . 108.38(10) ?
    C16 C11 C12 . . 121.86(11) ?
    C16 C11 O1 . . 114.58(10) ?
    C12 C11 O1 . . 123.52(11) ?
    C11 C12 C13 . . 118.12(12) ?
    C11 C12 H12A . . 120.9 ?
    C13 C12 H12A . . 120.9 ?
    C14 C13 C12 . . 120.90(13) ?
    C14 C13 H13A . . 119.6 ?
    C12 C13 H13A . . 119.6 ?
    C15 C14 C13 . . 119.61(12) ?
    C15 C14 H14A . . 120.2 ?
    C13 C14 H14A . . 120.2 ?
    C14 C15 C16 . . 120.25(12) ?
    C14 C15 H15A . . 119.9 ?
    C16 C15 H15A . . 119.9 ?
    C11 C16 C15 . . 119.26(12) ?
    C11 C16 H16A . . 120.4 ?
    C15 C16 H16A . . 120.4 ?
    N3 C17 C9 . . 122.87(10) ?
    N3 C17 S1 . . 113.56(8) ?
    C9 C17 S1 . . 123.54(9) ?
    N2 C18 N1 . . 122.82(11) ?
    N2 C18 S1 . . 113.65(9) ?
    N1 C18 S1 . . 123.52(10) ?
    C20 C19 C24 . . 119.10(13) ?
    C20 C19 H19A . . 120.4 ?
    C24 C19 H19A . . 120.4 ?
    C21 C20 C19 . . 120.55(14) ?
    C21 C20 H20A . . 119.7 ?
    C19 C20 H20A . . 119.7 ?
    C20 C21 C22 . . 119.89(13) ?
    C20 C21 H21A . . 120.1 ?
    C22 C21 H21A . . 120.1 ?
    C21 C22 C23 . . 120.51(15) ?
    C21 C22 H22A . . 119.7 ?
    C23 C22 H22A . . 119.7 ?
    C22 C23 C24 . . 119.09(15) ?
    C22 C23 H23A . . 120.5 ?
    C24 C23 H23A . . 120.5 ?
    C23 C24 C19 . . 120.84(12) ?
    C23 C24 N10 . . 118.13(12) ?
    C19 C24 N10 . . 120.95(11) ?
    C26 C25 H25A . . 109.5 ?
    C26 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    C26 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    N9 C26 C27 . . 111.09(11) ?
    N9 C26 C25 . . 120.35(11) ?
    C27 C26 C25 . . 128.55(11) ?
    C28 C27 C26 . . 104.34(10) ?
    C28 C27 C35 . . 127.21(11) ?
    C26 C27 C35 . . 128.21(11) ?
    O2 C28 N10 . . 122.78(11) ?
    O2 C28 C27 . . 128.84(11) ?
    N10 C28 C27 . . 108.27(11) ?
    C30 C29 C34 . . 121.48(13) ?
    C30 C29 O2 . . 123.56(11) ?
    C34 C29 O2 . . 114.95(12) ?
    C29 C30 C31 . . 118.28(14) ?
    C29 C30 H30A . . 120.9 ?
    C31 C30 H30A . . 120.9 ?
    C32 C31 C30 . . 121.03(17) ?
    C32 C31 H31A . . 119.5 ?
    C30 C31 H31A . . 119.5 ?
    C31 C32 C33 . . 119.66(15) ?
    C31 C32 H32A . . 120.2 ?
    C33 C32 H32A . . 120.2 ?
    C32 C33 C34 . . 120.81(15) ?
    C32 C33 H33A . . 119.6 ?
    C34 C33 H33A . . 119.6 ?
    C29 C34 C33 . . 118.74(15) ?
    C29 C34 H34A . . 120.6 ?
    C33 C34 H34A . . 120.6 ?
    N8 C35 C27 . . 123.33(11) ?
    N8 C35 S2 . . 113.75(9) ?
    C27 C35 S2 . . 122.91(9) ?
    N7 C36 N6 . . 123.00(12) ?
    N7 C36 S2 . . 113.89(9) ?
    N6 C36 S2 . . 123.06(10) ?
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
    C18 N2 N3 C17 . . . . -0.36(15) ?
    C8 N4 N5 C10 . . . . 0.95(13) ?
    C8 N4 N5 C6 . . . . -174.12(10) ?
    C36 N7 N8 C35 . . . . -0.94(17) ?
    C26 N9 N10 C28 . . . . 0.83(14) ?
    C26 N9 N10 C24 . . . . -172.83(11) ?
    C6 C1 C2 C3 . . . . 1.42(19) ?
    C1 C2 C3 C4 . . . . -0.8(2) ?
    C2 C3 C4 C5 . . . . -0.9(2) ?
    C3 C4 C5 C6 . . . . 2.0(2) ?
    C2 C1 C6 C5 . . . . -0.36(19) ?
    C2 C1 C6 N5 . . . . -177.25(11) ?
    C4 C5 C6 C1 . . . . -1.3(2) ?
    C4 C5 C6 N5 . . . . 175.65(13) ?
    C10 N5 C6 C1 . . . . -27.86(19) ?
    N4 N5 C6 C1 . . . . 146.09(11) ?
    C10 N5 C6 C5 . . . . 155.17(13) ?
    N4 N5 C6 C5 . . . . -30.88(17) ?
    N5 N4 C8 C9 . . . . -0.65(13) ?
    N5 N4 C8 C7 . . . . 178.21(11) ?
    N4 C8 C9 C10 . . . . 0.12(14) ?
    C7 C8 C9 C10 . . . . -178.63(12) ?
    N4 C8 C9 C17 . . . . 179.00(11) ?
    C7 C8 C9 C17 . . . . 0.3(2) ?
    C11 O1 C10 N5 . . . . -77.24(14) ?
    C11 O1 C10 C9 . . . . 106.74(14) ?
    N4 N5 C10 O1 . . . . -177.60(10) ?
    C6 N5 C10 O1 . . . . -3.22(19) ?
    N4 N5 C10 C9 . . . . -0.90(13) ?
    C6 N5 C10 C9 . . . . 173.49(11) ?
    C8 C9 C10 O1 . . . . 176.97(11) ?
    C17 C9 C10 O1 . . . . -1.9(2) ?
    C8 C9 C10 N5 . . . . 0.47(13) ?
    C17 C9 C10 N5 . . . . -178.42(11) ?
    C10 O1 C11 C16 . . . . 159.41(10) ?
    C10 O1 C11 C12 . . . . -22.92(16) ?
    C16 C11 C12 C13 . . . . 0.19(19) ?
    O1 C11 C12 C13 . . . . -177.32(11) ?
    C11 C12 C13 C14 . . . . 0.3(2) ?
    C12 C13 C14 C15 . . . . -0.5(2) ?
    C13 C14 C15 C16 . . . . 0.3(2) ?
    C12 C11 C16 C15 . . . . -0.36(19) ?
    O1 C11 C16 C15 . . . . 177.35(11) ?
    C14 C15 C16 C11 . . . . 0.1(2) ?
    N2 N3 C17 C9 . . . . 178.14(11) ?
    N2 N3 C17 S1 . . . . 0.10(13) ?
    C10 C9 C17 N3 . . . . 159.30(12) ?
    C8 C9 C17 N3 . . . . -19.3(2) ?
    C10 C9 C17 S1 . . . . -22.85(18) ?
    C8 C9 C17 S1 . . . . 158.51(10) ?
    C18 S1 C17 N3 . . . . 0.12(10) ?
    C18 S1 C17 C9 . . . . -177.90(11) ?
    N3 N2 C18 N1 . . . . 179.75(11) ?
    N3 N2 C18 S1 . . . . 0.46(14) ?
    C17 S1 C18 N2 . . . . -0.33(10) ?
    C17 S1 C18 N1 . . . . -179.62(12) ?
    C24 C19 C20 C21 . . . . 0.5(2) ?
    C19 C20 C21 C22 . . . . -0.9(2) ?
    C20 C21 C22 C23 . . . . 0.2(3) ?
    C21 C22 C23 C24 . . . . 0.8(2) ?
    C22 C23 C24 C19 . . . . -1.1(2) ?
    C22 C23 C24 N10 . . . . 175.63(13) ?
    C20 C19 C24 C23 . . . . 0.46(19) ?
    C20 C19 C24 N10 . . . . -176.23(11) ?
    C28 N10 C24 C23 . . . . 156.26(13) ?
    N9 N10 C24 C23 . . . . -31.54(17) ?
    C28 N10 C24 C19 . . . . -27.0(2) ?
    N9 N10 C24 C19 . . . . 145.24(12) ?
    N10 N9 C26 C27 . . . . -0.30(14) ?
    N10 N9 C26 C25 . . . . 178.83(11) ?
    N9 C26 C27 C28 . . . . -0.31(14) ?
    C25 C26 C27 C28 . . . . -179.36(13) ?
    N9 C26 C27 C35 . . . . 174.30(12) ?
    C25 C26 C27 C35 . . . . -4.7(2) ?
    C29 O2 C28 N10 . . . . -80.86(15) ?
    C29 O2 C28 C27 . . . . 103.48(15) ?
    N9 N10 C28 O2 . . . . -177.49(11) ?
    C24 N10 C28 O2 . . . . -4.8(2) ?
    N9 N10 C28 C27 . . . . -1.05(14) ?
    C24 N10 C28 C27 . . . . 171.67(12) ?
    C26 C27 C28 O2 . . . . 176.96(12) ?
    C35 C27 C28 O2 . . . . 2.3(2) ?
    C26 C27 C28 N10 . . . . 0.81(14) ?
    C35 C27 C28 N10 . . . . -173.88(12) ?
    C28 O2 C29 C30 . . . . -11.62(17) ?
    C28 O2 C29 C34 . . . . 169.42(11) ?
    C34 C29 C30 C31 . . . . 0.5(2) ?
    O2 C29 C30 C31 . . . . -178.34(13) ?
    C29 C30 C31 C32 . . . . 0.0(2) ?
    C30 C31 C32 C33 . . . . -0.5(2) ?
    C31 C32 C33 C34 . . . . 0.4(2) ?
    C30 C29 C34 C33 . . . . -0.6(2) ?
    O2 C29 C34 C33 . . . . 178.33(12) ?
    C32 C33 C34 C29 . . . . 0.2(2) ?
    N7 N8 C35 C27 . . . . -178.05(11) ?
    N7 N8 C35 S2 . . . . 0.50(15) ?
    C28 C27 C35 N8 . . . . 153.50(13) ?
    C26 C27 C35 N8 . . . . -19.9(2) ?
    C28 C27 C35 S2 . . . . -24.92(18) ?
    C26 C27 C35 S2 . . . . 161.64(11) ?
    C36 S2 C35 N8 . . . . 0.03(11) ?
    C36 S2 C35 C27 . . . . 178.59(11) ?
    N8 N7 C36 N6 . . . . -176.50(13) ?
    N8 N7 C36 S2 . . . . 0.97(15) ?
    C35 S2 C36 N7 . . . . -0.58(11) ?
    C35 S2 C36 N6 . . . . 176.89(13) ?
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
    N1 H1A N7 . 0.88 2.19 3.0266(16) 157.8
    N1 H1B N4 4_576 0.88 2.21 3.0113(15) 150.4
    N6 H6A N2 . 0.88 2.11 2.9467(15) 159.1
    N6 H6B N9 4_575 0.88 2.23 2.9915(16) 145.0
