##############################################################################
###                                                                        ###
###        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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data_global
_audit_creation_method     'SHELXL97'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-11-14
_journal_date_accepted     2007-12-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      2
_journal_page_first     o413
_journal_page_last     o413
_journal_paper_category     QO
_journal_coeditor_code     RK2066
_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
People's Republic of China
and School of Sciences
Xi'an Jiaotong University
Xian 710049
People's Republic of 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
;\
N-[(3-Methyl-5-phenoxy-1-phenylpyrazol-4-yl)carbonyl]-N'-(5-\
propyl-1,3,4-thiadiazol-2-yl)thiourea
;
loop_
    _publ_author_name
    _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
;
    'Yan-Ping Li'
;
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
;
data_I
_chemical_name_systematic
;
N-[(3-Methyl-5-phenoxy-1-phenylpyrazol-4-yl)carbonyl]-N'-(5-propyl-1,3,4-
thiadiazol-2-yl)thiourea
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H22 N6 O2 S2'
_chemical_formula_sum     'C23 H22 N6 O2 S2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C23 H22 N6 O2 S2'
_chemical_formula_weight     478.58
_chemical_melting_point        .461E-305
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.4489(3)
_cell_length_b     9.9099(4)
_cell_length_c     14.3492(5)
_cell_angle_alpha     86.0890(10)
_cell_angle_beta     74.0480(10)
_cell_angle_gamma     81.5910(10)
_cell_volume     1142.25(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     7971
_cell_measurement_theta_min     3.06
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     153(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.391
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     500
_exptl_absorpt_coefficient_mu     0.267
_exptl_absorpt_correction_type     empirical
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.9194
_exptl_absorpt_correction_T_max     0.9661
_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_reflns_number     11326
_diffrn_reflns_av_R_equivalents     0.0237
_diffrn_reflns_av_sigmaI/netI     0.0359
_diffrn_reflns_theta_min     3.05
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_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 > 2σ(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     5171
_reflns_number_gt     3376
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0755
_refine_ls_R_factor_gt     0.0420
_refine_ls_wR_factor_gt     0.1235
_refine_ls_wR_factor_ref     0.1646
_refine_ls_goodness_of_fit_ref     1.052
_refine_ls_restrained_S_all     1.052
_refine_ls_number_reflns     5171
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.1061P)²] 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     0.358
_refine_diff_density_min     -0.541
_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 (Rigaku 2004)'
_computing_data_reduction     'RAPID-AUTO (Rigaku 2004)'
_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 0.56160(7) 0.15893(6) 0.37164(4) 0.04016(19) Uani d . 1 . .
    S S2 0.56697(9) 0.18955(7) 0.58112(5) 0.0511(2) Uani d . 1 . .
    O O1 0.72651(18) 0.43251(15) 0.78717(10) 0.0330(3) Uani d . 1 . .
    O O2 0.7995(2) 0.57769(18) 0.48360(11) 0.0438(4) Uani d . 1 . .
    N N1 0.8356(2) 0.63699(19) 0.78887(13) 0.0328(4) Uani d . 1 . .
    N N2 0.8911(2) 0.74382(19) 0.72761(13) 0.0360(4) Uani d . 1 . .
    N N3 0.6887(2) 0.4151(2) 0.59251(13) 0.0346(4) Uani d . 1 . .
    H H3A 0.6652 0.3916 0.6546 0.042 Uiso calc R 1 . .
    N N4 0.6649(2) 0.3756(2) 0.44130(13) 0.0357(4) Uani d . 1 . .
    H H4A 0.7085 0.4522 0.4261 0.043 Uiso calc R 1 . .
    N N5 0.6442(3) 0.3835(2) 0.28420(14) 0.0439(5) Uani d . 1 . .
    N N6 0.6035(3) 0.3101(2) 0.21699(14) 0.0480(5) Uani d . 1 . .
    C C1 0.9603(3) 0.6775(3) 0.91597(18) 0.0408(5) Uani d . 1 . .
    H H1A 1.0540 0.7037 0.8681 0.049 Uiso calc R 1 . .
    C C2 0.9530(3) 0.6782(3) 1.01344(19) 0.0467(6) Uani d . 1 . .
    H H2B 1.0420 0.7061 1.0326 0.056 Uiso calc R 1 . .
    C C3 0.8177(3) 0.6388(3) 1.08327(18) 0.0452(6) Uani d . 1 . .
    H H3B 0.8146 0.6389 1.1500 0.054 Uiso calc R 1 . .
    C C4 0.6870(3) 0.5994(3) 1.05608(17) 0.0418(6) Uani d . 1 . .
    H H4B 0.5946 0.5714 1.1041 0.050 Uiso calc R 1 . .
    C C5 0.6905(3) 0.6005(2) 0.95854(16) 0.0364(5) Uani d . 1 . .
    H H5B 0.5996 0.5761 0.9395 0.044 Uiso calc R 1 . .
    C C6 0.8294(3) 0.6380(2) 0.88941(16) 0.0336(5) Uani d . 1 . .
    C C7 0.9194(3) 0.8149(3) 0.55833(18) 0.0433(6) Uani d . 1 . .
    H H7A 0.9635 0.8908 0.5786 0.065 Uiso calc R 1 . .
    H H7B 0.8206 0.8502 0.5366 0.065 Uiso calc R 1 . .
    H H7C 1.0040 0.7683 0.5050 0.065 Uiso calc R 1 . .
    C C8 0.8741(3) 0.7167(2) 0.64179(16) 0.0354(5) Uani d . 1 . .
    C C9 0.8061(3) 0.5921(2) 0.64604(15) 0.0325(5) Uani d . 1 . .
    C C10 0.7862(3) 0.5469(2) 0.74127(16) 0.0320(5) Uani d . 1 . .
    C C11 0.8364(3) 0.3093(2) 0.77255(14) 0.0283(4) Uani d . 1 . .
    C C12 0.7675(3) 0.1955(3) 0.81626(19) 0.0417(6) Uani d . 1 . .
    H H12A 0.6567 0.2036 0.8563 0.050 Uiso calc R 1 . .
    C C13 0.8630(3) 0.0697(3) 0.8006(2) 0.0516(7) Uani d . 1 . .
    H H13A 0.8178 -0.0100 0.8302 0.062 Uiso calc R 1 . .
    C C14 1.0242(3) 0.0589(3) 0.7422(2) 0.0530(7) Uani d . 1 . .
    H H14A 1.0888 -0.0282 0.7308 0.064 Uiso calc R 1 . .
    C C15 1.0906(3) 0.1736(3) 0.70074(19) 0.0473(6) Uani d . 1 . .
    H H15A 1.2016 0.1657 0.6609 0.057 Uiso calc R 1 . .
    C C16 0.9973(3) 0.3014(3) 0.71634(16) 0.0370(5) Uani d . 1 . .
    H H16A 1.0438 0.3814 0.6887 0.044 Uiso calc R 1 . .
    C C17 0.7669(3) 0.5307(2) 0.56726(16) 0.0329(5) Uani d . 1 . .
    C C18 0.6421(3) 0.3310(2) 0.53439(16) 0.0335(5) Uani d . 1 . .
    C C19 0.6281(3) 0.3158(2) 0.36680(16) 0.0351(5) Uani d . 1 . .
    C C20 0.5602(3) 0.1932(3) 0.25151(17) 0.0428(6) Uani d . 1 B .
    C C21 0.5096(4) 0.0933(3) 0.1944(2) 0.0555(7) Uani d . 1 . .
    H H21A 0.4153 0.0522 0.2383 0.067 Uiso calc R 1 A 1
    H H21B 0.4675 0.1455 0.1428 0.067 Uiso calc R 1 A 1
    C C22 0.6339(5) -0.0172(4) 0.1491(3) 0.0465(11) Uani d P 0.639(5) B 1
    H H22A 0.5827 -0.0767 0.1163 0.056 Uiso calc PR 0.639(5) B 1
    H H22B 0.6754 -0.0730 0.1995 0.056 Uiso calc PR 0.639(5) B 1
    C C23 0.7787(7) 0.0383(5) 0.0753(3) 0.0568(13) Uani d P 0.639(5) B 1
    H H23A 0.8616 -0.0378 0.0465 0.085 Uiso calc PR 0.639(5) B 1
    H H23B 0.8293 0.0972 0.1077 0.085 Uiso calc PR 0.639(5) B 1
    H H23C 0.7381 0.0912 0.0243 0.085 Uiso calc PR 0.639(5) B 1
    C C22' 0.6510(12) 0.0828(9) 0.0931(5) 0.053(2) Uani d P 0.361(5) B 2
    H H22C 0.6563 0.1730 0.0591 0.064 Uiso calc PR 0.361(5) B 2
    H H22D 0.7611 0.0490 0.1038 0.064 Uiso calc PR 0.361(5) B 2
    C C23' 0.6019(12) -0.0149(10) 0.0362(6) 0.064(3) Uani d P 0.361(5) B 2
    H H23D 0.6845 -0.0268 -0.0267 0.096 Uiso calc PR 0.361(5) B 2
    H H23E 0.4931 0.0205 0.0260 0.096 Uiso calc PR 0.361(5) B 2
    H H23F 0.5954 -0.1029 0.0715 0.096 Uiso calc PR 0.361(5) B 2
_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 C19 . 1.719(2) ?
    S1 C20 . 1.737(2) ?
    S2 C18 . 1.648(2) ?
    O1 C10 . 1.362(3) ?
    O1 C11 . 1.411(3) ?
    O2 C17 . 1.230(3) ?
    N1 C10 . 1.337(3) ?
    N1 N2 . 1.380(2) ?
    N1 C6 . 1.430(3) ?
    N2 C8 . 1.328(3) ?
    N3 C17 . 1.383(3) ?
    N3 C18 . 1.384(3) ?
    N3 H3A . 0.8800 ?
    N4 C18 . 1.349(3) ?
    N4 C19 . 1.384(3) ?
    N4 H4A . 0.8800 ?
    N5 C19 . 1.305(3) ?
    N5 N6 . 1.389(3) ?
    N6 C20 . 1.292(3) ?
    C1 C6 . 1.379(3) ?
    C1 C2 . 1.383(3) ?
    C1 H1A . 0.9500 ?
    C2 C3 . 1.382(4) ?
    C2 H2B . 0.9500 ?
    C3 C4 . 1.381(3) ?
    C3 H3B . 0.9500 ?
    C4 C5 . 1.391(3) ?
    C4 H4B . 0.9500 ?
    C5 C6 . 1.392(3) ?
    C5 H5B . 0.9500 ?
    C7 C8 . 1.492(3) ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
    C8 C9 . 1.427(3) ?
    C9 C10 . 1.381(3) ?
    C9 C17 . 1.455(3) ?
    C11 C16 . 1.371(3) ?
    C11 C12 . 1.378(3) ?
    C12 C13 . 1.378(4) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.382(4) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.368(4) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.387(3) ?
    C15 H15A . 0.9500 ?
    C16 H16A . 0.9500 ?
    C20 C21 . 1.503(4) ?
    C21 C22 . 1.453(5) ?
    C21 C22' . 1.607(8) ?
    C21 H21A . 0.9900 ?
    C21 H21B . 0.9900 ?
    C22 C23 . 1.525(6) ?
    C22 H22A . 0.9900 ?
    C22 H22B . 0.9900 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
    C22' C23' . 1.479(10) ?
    C22' H22C . 0.9900 ?
    C22' H22D . 0.9900 ?
    C23' H23D . 0.9800 ?
    C23' H23E . 0.9800 ?
    C23' H23F . 0.9800 ?
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
    C19 S1 C20 . . 85.87(11) ?
    C10 O1 C11 . . 116.95(16) ?
    C10 N1 N2 . . 110.63(17) ?
    C10 N1 C6 . . 129.28(19) ?
    N2 N1 C6 . . 120.00(17) ?
    C8 N2 N1 . . 105.57(18) ?
    C17 N3 C18 . . 129.42(18) ?
    C17 N3 H3A . . 115.3 ?
    C18 N3 H3A . . 115.3 ?
    C18 N4 C19 . . 128.0(2) ?
    C18 N4 H4A . . 116.0 ?
    C19 N4 H4A . . 116.0 ?
    C19 N5 N6 . . 111.0(2) ?
    C20 N6 N5 . . 112.6(2) ?
    C6 C1 C2 . . 118.9(2) ?
    C6 C1 H1A . . 120.5 ?
    C2 C1 H1A . . 120.5 ?
    C3 C2 C1 . . 120.8(2) ?
    C3 C2 H2B . . 119.6 ?
    C1 C2 H2B . . 119.6 ?
    C4 C3 C2 . . 120.0(2) ?
    C4 C3 H3B . . 120.0 ?
    C2 C3 H3B . . 120.0 ?
    C3 C4 C5 . . 120.1(2) ?
    C3 C4 H4B . . 119.9 ?
    C5 C4 H4B . . 119.9 ?
    C4 C5 C6 . . 118.9(2) ?
    C4 C5 H5B . . 120.6 ?
    C6 C5 H5B . . 120.6 ?
    C1 C6 C5 . . 121.3(2) ?
    C1 C6 N1 . . 119.4(2) ?
    C5 C6 N1 . . 119.32(19) ?
    C8 C7 H7A . . 109.5 ?
    C8 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C8 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    N2 C8 C9 . . 111.13(19) ?
    N2 C8 C7 . . 119.6(2) ?
    C9 C8 C7 . . 129.2(2) ?
    C10 C9 C8 . . 103.68(19) ?
    C10 C9 C17 . . 129.3(2) ?
    C8 C9 C17 . . 127.0(2) ?
    N1 C10 O1 . . 121.07(19) ?
    N1 C10 C9 . . 108.98(19) ?
    O1 C10 C9 . . 130.0(2) ?
    C16 C11 C12 . . 122.1(2) ?
    C16 C11 O1 . . 123.2(2) ?
    C12 C11 O1 . . 114.70(18) ?
    C11 C12 C13 . . 118.6(2) ?
    C11 C12 H12A . . 120.7 ?
    C13 C12 H12A . . 120.7 ?
    C12 C13 C14 . . 120.3(2) ?
    C12 C13 H13A . . 119.8 ?
    C14 C13 H13A . . 119.8 ?
    C15 C14 C13 . . 120.0(2) ?
    C15 C14 H14A . . 120.0 ?
    C13 C14 H14A . . 120.0 ?
    C14 C15 C16 . . 120.6(2) ?
    C14 C15 H15A . . 119.7 ?
    C16 C15 H15A . . 119.7 ?
    C11 C16 C15 . . 118.4(2) ?
    C11 C16 H16A . . 120.8 ?
    C15 C16 H16A . . 120.8 ?
    O2 C17 N3 . . 121.6(2) ?
    O2 C17 C9 . . 122.9(2) ?
    N3 C17 C9 . . 115.49(19) ?
    N4 C18 N3 . . 114.41(19) ?
    N4 C18 S2 . . 125.85(18) ?
    N3 C18 S2 . . 119.73(16) ?
    N5 C19 N4 . . 117.9(2) ?
    N5 C19 S1 . . 115.74(18) ?
    N4 C19 S1 . . 126.40(17) ?
    N6 C20 C21 . . 123.7(2) ?
    N6 C20 S1 . . 114.75(18) ?
    C21 C20 S1 . . 121.5(2) ?
    C22 C21 C20 . . 118.1(3) ?
    C22 C21 C22' . . 47.1(4) ?
    C20 C21 C22' . . 104.9(3) ?
    C22 C21 H21A . . 107.8 ?
    C20 C21 H21A . . 107.8 ?
    C22' C21 H21A . . 146.2 ?
    C22 C21 H21B . . 107.8 ?
    C20 C21 H21B . . 107.8 ?
    C22' C21 H21B . . 69.9 ?
    H21A C21 H21B . . 107.1 ?
    C21 C22 C23 . . 110.9(4) ?
    C21 C22 H22A . . 109.5 ?
    C23 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    C23 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 108.0 ?
    C22 C23 H23A . . 109.5 ?
    C22 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C22 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C23' C22' C21 . . 105.3(6) ?
    C23' C22' H22C . . 110.7 ?
    C21 C22' H22C . . 110.7 ?
    C23' C22' H22D . . 110.7 ?
    C21 C22' H22D . . 110.7 ?
    H22C C22' H22D . . 108.8 ?
    C22' C23' H23D . . 109.5 ?
    C22' C23' H23E . . 109.5 ?
    H23D C23' H23E . . 109.5 ?
    C22' C23' H23F . . 109.5 ?
    H23D C23' H23F . . 109.5 ?
    H23E C23' H23F . . 109.5 ?
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
    C10 N1 N2 C8 . . . . 0.1(2) ?
    C6 N1 N2 C8 . . . . -176.87(19) ?
    C19 N5 N6 C20 . . . . -0.2(3) ?
    C6 C1 C2 C3 . . . . 0.6(4) ?
    C1 C2 C3 C4 . . . . -0.6(4) ?
    C2 C3 C4 C5 . . . . -0.6(4) ?
    C3 C4 C5 C6 . . . . 1.9(4) ?
    C2 C1 C6 C5 . . . . 0.6(4) ?
    C2 C1 C6 N1 . . . . 179.9(2) ?
    C4 C5 C6 C1 . . . . -1.9(4) ?
    C4 C5 C6 N1 . . . . 178.8(2) ?
    C10 N1 C6 C1 . . . . 140.6(2) ?
    N2 N1 C6 C1 . . . . -43.1(3) ?
    C10 N1 C6 C5 . . . . -40.1(3) ?
    N2 N1 C6 C5 . . . . 136.3(2) ?
    N1 N2 C8 C9 . . . . 0.4(2) ?
    N1 N2 C8 C7 . . . . 178.47(19) ?
    N2 C8 C9 C10 . . . . -0.7(2) ?
    C7 C8 C9 C10 . . . . -178.6(2) ?
    N2 C8 C9 C17 . . . . 178.7(2) ?
    C7 C8 C9 C17 . . . . 0.9(4) ?
    N2 N1 C10 O1 . . . . 179.90(18) ?
    C6 N1 C10 O1 . . . . -3.5(3) ?
    N2 N1 C10 C9 . . . . -0.6(2) ?
    C6 N1 C10 C9 . . . . 176.1(2) ?
    C11 O1 C10 N1 . . . . -101.1(2) ?
    C11 O1 C10 C9 . . . . 79.5(3) ?
    C8 C9 C10 N1 . . . . 0.7(2) ?
    C17 C9 C10 N1 . . . . -178.7(2) ?
    C8 C9 C10 O1 . . . . -179.8(2) ?
    C17 C9 C10 O1 . . . . 0.8(4) ?
    C10 O1 C11 C16 . . . . 0.9(3) ?
    C10 O1 C11 C12 . . . . -176.69(18) ?
    C16 C11 C12 C13 . . . . -1.7(4) ?
    O1 C11 C12 C13 . . . . 175.9(2) ?
    C11 C12 C13 C14 . . . . -0.1(4) ?
    C12 C13 C14 C15 . . . . 1.1(4) ?
    C13 C14 C15 C16 . . . . -0.4(4) ?
    C12 C11 C16 C15 . . . . 2.3(3) ?
    O1 C11 C16 C15 . . . . -175.1(2) ?
    C14 C15 C16 C11 . . . . -1.3(4) ?
    C18 N3 C17 O2 . . . . 3.3(4) ?
    C18 N3 C17 C9 . . . . -177.0(2) ?
    C10 C9 C17 O2 . . . . -175.8(2) ?
    C8 C9 C17 O2 . . . . 5.0(4) ?
    C10 C9 C17 N3 . . . . 4.6(3) ?
    C8 C9 C17 N3 . . . . -174.7(2) ?
    C19 N4 C18 N3 . . . . -178.9(2) ?
    C19 N4 C18 S2 . . . . 1.5(3) ?
    C17 N3 C18 N4 . . . . -5.9(3) ?
    C17 N3 C18 S2 . . . . 173.78(18) ?
    N6 N5 C19 N4 . . . . 179.78(19) ?
    N6 N5 C19 S1 . . . . -0.4(3) ?
    C18 N4 C19 N5 . . . . 173.0(2) ?
    C18 N4 C19 S1 . . . . -6.8(3) ?
    C20 S1 C19 N5 . . . . 0.63(19) ?
    C20 S1 C19 N4 . . . . -179.6(2) ?
    N5 N6 C20 C21 . . . . 179.9(2) ?
    N5 N6 C20 S1 . . . . 0.7(3) ?
    C19 S1 C20 N6 . . . . -0.7(2) ?
    C19 S1 C20 C21 . . . . -179.9(2) ?
    N6 C20 C21 C22 . . . . 97.3(4) ?
    S1 C20 C21 C22 . . . . -83.6(3) ?
    N6 C20 C21 C22' . . . . 48.3(5) ?
    S1 C20 C21 C22' . . . . -132.6(4) ?
    C20 C21 C22 C23 . . . . -61.3(4) ?
    C22' C21 C22 C23 . . . . 23.1(5) ?
    C22 C21 C22' C23' . . . . 65.6(6) ?
    C20 C21 C22' C23' . . . . -179.7(6) ?
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
    N3 H3A O1 . 0.88 2.18 2.917(2) 140.6
    N4 H4A O2 . 0.88 1.89 2.623(2) 139.2
