##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2007-03-19
_journal_date_accepted     2007-03-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      5
_journal_page_first     o2363
_journal_page_last     o2364
_journal_paper_category     EO
_journal_coeditor_code     HK2222
_publ_contact_author_name     ' Wan, Rong'
_publ_contact_author_address
;
Department of Applied Chemistry
College of Science
Nanjing University of Technology
No.5 Xinmofan Road, Nanjing
Nanjing 210009
People's Republic of China
;
_publ_contact_author_email     rwan01@jlonline.com
_publ_contact_author_fax     '86 25 83369345'
_publ_contact_author_phone     '86 25 83587440'
_publ_section_title
;
N-Benzylidene-5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-amine
;
loop_
    _publ_author_name
    _publ_author_address
    'Wan, Rong'
;
Department of Applied Chemistry
College of Science
Nanjing University of Technology
No. 5 Xinmofan Road,
Nanjing 210009
People's Republic of China
;
    'Ni, Jue-Ping'
;
Bioactivity Test Center
Jiangsu Branch of National Pesticide R & D South Center
No. 80 Luosi Bridge,
Nanjing 210019
People's Republic of China
;
    'Han, Feng'
;
Department of Applied Chemistry
College of Science
Nanjing University of Technology
No. 5 Xinmofan Road,
Nanjing 210009
People's Republic of China
;
    'Zhang, Jin-Jun'
;
Department of Applied Chemistry
College of Science
Nanjing University of Technology
No. 5 Xinmofan Road,
Nanjing 210009
People's Republic of China
;
    'Wang, Jin-Tang'
;
Department of Applied Chemistry
College of Science
Nanjing University of Technology
No. 5 Xinmofan Road,
Nanjing 210009
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-benzylidene-5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H13 N3 O S'
_chemical_formula_sum     'C16 H13 N3 O S'
_chemical_formula_iupac     'C16 H13 N3 O S'
_chemical_formula_weight     295.36
_chemical_melting_point     408
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_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'
_cell_length_a     7.4253(7)
_cell_length_b     11.5124(11)
_cell_length_c     33.0405(19)
_cell_angle_alpha     90.00
_cell_angle_beta     93.10(3)
_cell_angle_gamma     90.00
_cell_volume     2820.3(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9
_cell_measurement_theta_max     12
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.391
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1232
_exptl_absorpt_coefficient_mu     0.231
_exptl_absorpt_correction_type     'psi-scan'
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.9552
_exptl_absorpt_correction_T_max     0.9772
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(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     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5940
_diffrn_reflns_av_R_equivalents     0.0631
_diffrn_reflns_av_sigmaI/netI     0.0357
_diffrn_reflns_theta_min     1.23
_diffrn_reflns_theta_max     25.97
_diffrn_reflns_theta_full     25.97
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     40
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     0
_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     5517
_reflns_number_gt     2748
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1320
_refine_ls_R_factor_gt     0.0772
_refine_ls_wR_factor_gt     0.1514
_refine_ls_wR_factor_ref     0.1818
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     5517
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.04P)²+P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.130
_refine_diff_density_min     -0.128
_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     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Siemens, 1996)'
_computing_publication_material     'SHELXL97'
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 S1A -0.96674(19) 0.16823(11) -0.35400(4) 0.1159(4) Uani d . 1 . .
    O O1A -0.7959(5) 0.2398(3) -0.15280(11) 0.1242(11) Uani d . 1 . .
    C C7A -1.1023(6) 0.1575(4) -0.44499(15) 0.1083(13) Uani d . 1 . .
    H H7A -1.1408 0.1058 -0.4256 0.130 Uiso calc R 1 . .
    N N2A -0.9606(6) 0.3781(4) -0.37976(14) 0.1221(13) Uani d . 1 . .
    N N3A -0.9313(6) 0.3822(4) -0.33829(14) 0.1220(13) Uani d . 1 . .
    C C1A -1.0670(7) 0.1961(5) -0.51795(17) 0.1184(16) Uani d . 1 . .
    H H1A -0.9920 0.2585 -0.5111 0.142 Uiso calc R 1 . .
    C C2A -1.1050(7) 0.1701(5) -0.55798(17) 0.1234(16) Uani d . 1 . .
    H H2A -1.0554 0.2144 -0.5781 0.148 Uiso calc R 1 . .
    C C3A -1.2180(8) 0.0774(6) -0.56835(17) 0.1274(17) Uani d . 1 . .
    H H3A -1.2468 0.0608 -0.5955 0.153 Uiso calc R 1 . .
    C C4A -1.2867(7) 0.0107(5) -0.53891(18) 0.1286(17) Uani d . 1 . .
    H H4A -1.3611 -0.0519 -0.5459 0.154 Uiso calc R 1 . .
    C C5A -1.2462(7) 0.0360(5) -0.49883(17) 0.1170(15) Uani d . 1 . .
    H H5A -1.2914 -0.0110 -0.4789 0.140 Uiso calc R 1 . .
    C C6A -1.1389(6) 0.1305(4) -0.48766(15) 0.1044(13) Uani d . 1 . .
    N N1A -1.0196(6) 0.2492(4) -0.43307(13) 0.1135(12) Uani d . 1 . .
    C C8A -0.9877(7) 0.2716(5) -0.39226(16) 0.1057(14) Uani d . 1 . .
    C C9A -0.9290(6) 0.2824(4) -0.32011(16) 0.1023(13) Uani d . 1 . .
    C C10A -0.8939(6) 0.2659(4) -0.27746(16) 0.1044(13) Uani d . 1 . .
    C C11A -0.8283(6) 0.3588(4) -0.25327(16) 0.1073(13) Uani d . 1 . .
    H H11A -0.8056 0.4298 -0.2654 0.129 Uiso calc R 1 . .
    C C12A -0.7970(6) 0.3469(4) -0.21227(16) 0.1120(14) Uani d . 1 . .
    H H12A -0.7529 0.4095 -0.1969 0.134 Uiso calc R 1 . .
    C C13A -0.8311(7) 0.2413(5) -0.19337(16) 0.1101(14) Uani d . 1 . .
    C C14A -0.8956(6) 0.1498(4) -0.21647(15) 0.1085(13) Uani d . 1 . .
    H H14A -0.9174 0.0787 -0.2043 0.130 Uiso calc R 1 . .
    C C15A -0.9279(6) 0.1632(4) -0.25756(15) 0.1105(14) Uani d . 1 . .
    H H15A -0.9746 0.1007 -0.2726 0.133 Uiso calc R 1 . .
    C C16A -0.8176(8) 0.1293(5) -0.13329(15) 0.143(2) Uani d . 1 . .
    H H16C -0.7903 0.1373 -0.1047 0.215 Uiso calc R 1 . .
    H H16B -0.7372 0.0737 -0.1443 0.215 Uiso calc R 1 . .
    H H16A -0.9398 0.1032 -0.1379 0.215 Uiso calc R 1 . .
    S S1B -1.05294(19) -0.16176(11) -0.15227(4) 0.1145(4) Uani d . 1 . .
    O O1B -1.2098(5) -0.2250(3) -0.35440(10) 0.1243(11) Uani d . 1 . .
    C C7B -0.9097(6) -0.1513(4) -0.06168(14) 0.1079(13) Uani d . 1 . .
    H H7B -0.8806 -0.0968 -0.0810 0.129 Uiso calc R 1 . .
    N N2B -1.0263(6) -0.3716(4) -0.12832(13) 0.1223(13) Uani d . 1 . .
    N N3B -1.0579(6) -0.3770(3) -0.16995(13) 0.1223(13) Uani d . 1 . .
    C C1B -0.7581(7) -0.0327(5) -0.00898(16) 0.1161(15) Uani d . 1 . .
    H H1B -0.7171 0.0154 -0.0292 0.139 Uiso calc R 1 . .
    C C2B -0.7090(7) -0.0088(5) 0.03105(18) 0.1238(16) Uani d . 1 . .
    H H2B -0.6347 0.0542 0.0377 0.149 Uiso calc R 1 . .
    C C3B -0.7711(8) -0.0794(6) 0.06109(17) 0.1300(18) Uani d . 1 . .
    H H3B -0.7383 -0.0643 0.0881 0.156 Uiso calc R 1 . .
    C C4B -0.8817(8) -0.1722(5) 0.05105(17) 0.1262(17) Uani d . 1 . .
    H H4B -0.9245 -0.2189 0.0714 0.151 Uiso calc R 1 . .
    C C5B -0.9288(7) -0.1960(5) 0.01135(16) 0.1147(15) Uani d . 1 . .
    H H5B -1.0029 -0.2591 0.0049 0.138 Uiso calc R 1 . .
    C C6B -0.8662(7) -0.1259(4) -0.01973(14) 0.1035(13) Uani d . 1 . .
    N N1B -0.9866(6) -0.2455(4) -0.07363(13) 0.1091(12) Uani d . 1 . .
    C C8B -1.0180(7) -0.2647(4) -0.11495(16) 0.1086(14) Uani d . 1 . .
    C C9B -1.0742(6) -0.2743(4) -0.18673(15) 0.1033(13) Uani d . 1 . .
    C C10B -1.1107(6) -0.2575(4) -0.23040(14) 0.0989(12) Uani d . 1 . .
    C C11B -1.0797(6) -0.3497(4) -0.25734(15) 0.1072(13) Uani d . 1 . .
    H H11B -1.0349 -0.4202 -0.2474 0.129 Uiso calc R 1 . .
    C C12B -1.1154(6) -0.3354(5) -0.29794(15) 0.1111(14) Uani d . 1 . .
    H H12B -1.0967 -0.3967 -0.3155 0.133 Uiso calc R 1 . .
    C C13B -1.1795(7) -0.2298(4) -0.31327(15) 0.1031(13) Uani d . 1 . .
    C C14B -1.2111(6) -0.1380(4) -0.28740(14) 0.1088(14) Uani d . 1 . .
    H H14B -1.2546 -0.0674 -0.2975 0.131 Uiso calc R 1 . .
    C C15B -1.1760(6) -0.1543(4) -0.24619(14) 0.1035(12) Uani d . 1 . .
    H H15B -1.1974 -0.0934 -0.2286 0.124 Uiso calc R 1 . .
    C C16B -1.2734(8) -0.1175(4) -0.37071(15) 0.1358(19) Uani d . 1 . .
    H H16F -1.2909 -0.1241 -0.3996 0.204 Uiso calc R 1 . .
    H H16E -1.1864 -0.0577 -0.3642 0.204 Uiso calc R 1 . .
    H H16D -1.3858 -0.0980 -0.3594 0.204 Uiso calc R 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
    S1A C8A . 1.737(5) ?
    S1A C9A . 1.740(5) ?
    O1A C13A . 1.352(6) ?
    O1A C16A . 1.439(6) ?
    C7A N1A . 1.273(5) ?
    C7A C6A . 1.455(6) ?
    C7A H7A . 0.9300 ?
    N2A C8A . 1.306(6) ?
    N2A N3A . 1.377(5) ?
    N3A C9A . 1.296(6) ?
    C1A C2A . 1.370(6) ?
    C1A C6A . 1.384(6) ?
    C1A H1A . 0.9300 ?
    C2A C3A . 1.390(7) ?
    C2A H2A . 0.9300 ?
    C3A C4A . 1.360(7) ?
    C3A H3A . 0.9300 ?
    C4A C5A . 1.373(7) ?
    C4A H4A . 0.9300 ?
    C5A C6A . 1.386(6) ?
    C5A H5A . 0.9300 ?
    N1A C8A . 1.381(6) ?
    C9A C10A . 1.432(6) ?
    C10A C15A . 1.383(6) ?
    C10A C11A . 1.407(6) ?
    C11A C12A . 1.369(6) ?
    C11A H11A . 0.9300 ?
    C12A C13A . 1.396(6) ?
    C12A H12A . 0.9300 ?
    C13A C14A . 1.372(6) ?
    C14A C15A . 1.375(6) ?
    C14A H14A . 0.9300 ?
    C15A H15A . 0.9300 ?
    C16A H16C . 0.9600 ?
    C16A H16B . 0.9600 ?
    C16A H16A . 0.9600 ?
    S1B C8B . 1.719(5) ?
    S1B C9B . 1.727(5) ?
    O1B C13B . 1.367(5) ?
    O1B C16B . 1.420(5) ?
    C7B N1B . 1.278(5) ?
    C7B C6B . 1.436(6) ?
    C7B H7B . 0.9300 ?
    N2B C8B . 1.308(6) ?
    N2B N3B . 1.384(5) ?
    N3B C9B . 1.308(5) ?
    C1B C6B . 1.376(6) ?
    C1B C2B . 1.381(6) ?
    C1B H1B . 0.9300 ?
    C2B C3B . 1.382(7) ?
    C2B H2B . 0.9300 ?
    C3B C4B . 1.376(7) ?
    C3B H3B . 0.9300 ?
    C4B C5B . 1.367(6) ?
    C4B H4B . 0.9300 ?
    C5B C6B . 1.405(6) ?
    C5B H5B . 0.9300 ?
    N1B C8B . 1.390(6) ?
    C9B C10B . 1.466(6) ?
    C10B C15B . 1.375(6) ?
    C10B C11B . 1.413(6) ?
    C11B C12B . 1.363(6) ?
    C11B H11B . 0.9300 ?
    C12B C13B . 1.391(6) ?
    C12B H12B . 0.9300 ?
    C13B C14B . 1.387(6) ?
    C14B C15B . 1.385(6) ?
    C14B H14B . 0.9300 ?
    C15B H15B . 0.9300 ?
    C16B H16F . 0.9600 ?
    C16B H16E . 0.9600 ?
    C16B H16D . 0.9600 ?
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
    C8A S1A C9A . . 87.5(3) ?
    C13A O1A C16A . . 115.8(4) ?
    N1A C7A C6A . . 122.6(5) ?
    N1A C7A H7A . . 118.7 ?
    C6A C7A H7A . . 118.7 ?
    C8A N2A N3A . . 111.1(4) ?
    C9A N3A N2A . . 115.4(4) ?
    C2A C1A C6A . . 120.8(5) ?
    C2A C1A H1A . . 119.6 ?
    C6A C1A H1A . . 119.6 ?
    C1A C2A C3A . . 119.7(5) ?
    C1A C2A H2A . . 120.2 ?
    C3A C2A H2A . . 120.2 ?
    C4A C3A C2A . . 120.1(6) ?
    C4A C3A H3A . . 119.9 ?
    C2A C3A H3A . . 119.9 ?
    C3A C4A C5A . . 120.0(6) ?
    C3A C4A H4A . . 120.0 ?
    C5A C4A H4A . . 120.0 ?
    C4A C5A C6A . . 121.0(5) ?
    C4A C5A H5A . . 119.5 ?
    C6A C5A H5A . . 119.5 ?
    C1A C6A C5A . . 118.3(5) ?
    C1A C6A C7A . . 121.6(5) ?
    C5A C6A C7A . . 120.0(5) ?
    C7A N1A C8A . . 120.7(5) ?
    N2A C8A N1A . . 120.0(5) ?
    N2A C8A S1A . . 114.0(4) ?
    N1A C8A S1A . . 125.9(4) ?
    N3A C9A C10A . . 124.8(5) ?
    N3A C9A S1A . . 112.0(4) ?
    C10A C9A S1A . . 123.2(4) ?
    C15A C10A C11A . . 116.5(5) ?
    C15A C10A C9A . . 123.6(5) ?
    C11A C10A C9A . . 119.8(5) ?
    C12A C11A C10A . . 121.4(5) ?
    C12A C11A H11A . . 119.3 ?
    C10A C11A H11A . . 119.3 ?
    C11A C12A C13A . . 120.3(5) ?
    C11A C12A H12A . . 119.9 ?
    C13A C12A H12A . . 119.9 ?
    O1A C13A C14A . . 125.8(5) ?
    O1A C13A C12A . . 115.1(5) ?
    C14A C13A C12A . . 119.1(5) ?
    C13A C14A C15A . . 120.0(5) ?
    C13A C14A H14A . . 120.0 ?
    C15A C14A H14A . . 120.0 ?
    C14A C15A C10A . . 122.6(5) ?
    C14A C15A H15A . . 118.7 ?
    C10A C15A H15A . . 118.7 ?
    O1A C16A H16C . . 109.5 ?
    O1A C16A H16B . . 109.5 ?
    H16C C16A H16B . . 109.5 ?
    O1A C16A H16A . . 109.5 ?
    H16C C16A H16A . . 109.5 ?
    H16B C16A H16A . . 109.5 ?
    C8B S1B C9B . . 87.7(2) ?
    C13B O1B C16B . . 116.5(4) ?
    N1B C7B C6B . . 123.0(5) ?
    N1B C7B H7B . . 118.5 ?
    C6B C7B H7B . . 118.5 ?
    C8B N2B N3B . . 112.3(4) ?
    C9B N3B N2B . . 112.8(4) ?
    C6B C1B C2B . . 121.5(5) ?
    C6B C1B H1B . . 119.2 ?
    C2B C1B H1B . . 119.2 ?
    C1B C2B C3B . . 119.3(5) ?
    C1B C2B H2B . . 120.3 ?
    C3B C2B H2B . . 120.3 ?
    C4B C3B C2B . . 120.1(6) ?
    C4B C3B H3B . . 119.9 ?
    C2B C3B H3B . . 119.9 ?
    C5B C4B C3B . . 120.3(6) ?
    C5B C4B H4B . . 119.8 ?
    C3B C4B H4B . . 119.8 ?
    C4B C5B C6B . . 120.6(5) ?
    C4B C5B H5B . . 119.7 ?
    C6B C5B H5B . . 119.7 ?
    C1B C6B C5B . . 118.1(5) ?
    C1B C6B C7B . . 120.4(5) ?
    C5B C6B C7B . . 121.5(5) ?
    C7B N1B C8B . . 119.1(4) ?
    N2B C8B N1B . . 118.9(5) ?
    N2B C8B S1B . . 113.8(4) ?
    N1B C8B S1B . . 127.3(4) ?
    N3B C9B C10B . . 123.0(5) ?
    N3B C9B S1B . . 113.3(4) ?
    C10B C9B S1B . . 123.7(4) ?
    C15B C10B C11B . . 118.4(4) ?
    C15B C10B C9B . . 122.0(5) ?
    C11B C10B C9B . . 119.5(4) ?
    C12B C11B C10B . . 120.0(5) ?
    C12B C11B H11B . . 120.0 ?
    C10B C11B H11B . . 120.0 ?
    C11B C12B C13B . . 120.6(5) ?
    C11B C12B H12B . . 119.7 ?
    C13B C12B H12B . . 119.7 ?
    O1B C13B C14B . . 123.9(5) ?
    O1B C13B C12B . . 115.6(4) ?
    C14B C13B C12B . . 120.5(5) ?
    C15B C14B C13B . . 118.3(5) ?
    C15B C14B H14B . . 120.9 ?
    C13B C14B H14B . . 120.9 ?
    C10B C15B C14B . . 122.3(5) ?
    C10B C15B H15B . . 118.9 ?
    C14B C15B H15B . . 118.9 ?
    O1B C16B H16F . . 109.5 ?
    O1B C16B H16E . . 109.5 ?
    H16F C16B H16E . . 109.5 ?
    O1B C16B H16D . . 109.5 ?
    H16F C16B H16D . . 109.5 ?
    H16E C16B H16D . . 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
    C8A N2A N3A C9A . . . . 2.6(7) ?
    C6A C1A C2A C3A . . . . 0.4(8) ?
    C1A C2A C3A C4A . . . . -1.8(8) ?
    C2A C3A C4A C5A . . . . 0.8(8) ?
    C3A C4A C5A C6A . . . . 1.5(8) ?
    C2A C1A C6A C5A . . . . 1.8(8) ?
    C2A C1A C6A C7A . . . . -179.1(5) ?
    C4A C5A C6A C1A . . . . -2.7(8) ?
    C4A C5A C6A C7A . . . . 178.1(5) ?
    N1A C7A C6A C1A . . . . 7.9(8) ?
    N1A C7A C6A C5A . . . . -173.0(5) ?
    C6A C7A N1A C8A . . . . 180.0(4) ?
    N3A N2A C8A N1A . . . . -180.0(4) ?
    N3A N2A C8A S1A . . . . -3.3(6) ?
    C7A N1A C8A N2A . . . . -156.9(5) ?
    C7A N1A C8A S1A . . . . 26.9(7) ?
    C9A S1A C8A N2A . . . . 2.5(4) ?
    C9A S1A C8A N1A . . . . 178.9(5) ?
    N2A N3A C9A C10A . . . . 177.4(4) ?
    N2A N3A C9A S1A . . . . -0.6(6) ?
    C8A S1A C9A N3A . . . . -1.0(4) ?
    C8A S1A C9A C10A . . . . -179.1(4) ?
    N3A C9A C10A C15A . . . . 166.2(5) ?
    S1A C9A C10A C15A . . . . -15.9(7) ?
    N3A C9A C10A C11A . . . . -11.0(8) ?
    S1A C9A C10A C11A . . . . 166.9(4) ?
    C15A C10A C11A C12A . . . . 1.1(7) ?
    C9A C10A C11A C12A . . . . 178.5(4) ?
    C10A C11A C12A C13A . . . . -0.4(7) ?
    C16A O1A C13A C14A . . . . 4.4(8) ?
    C16A O1A C13A C12A . . . . -175.6(5) ?
    C11A C12A C13A O1A . . . . -179.8(4) ?
    C11A C12A C13A C14A . . . . 0.2(8) ?
    O1A C13A C14A C15A . . . . 179.2(5) ?
    C12A C13A C14A C15A . . . . -0.8(8) ?
    C13A C14A C15A C10A . . . . 1.7(8) ?
    C11A C10A C15A C14A . . . . -1.8(7) ?
    C9A C10A C15A C14A . . . . -179.0(5) ?
    C8B N2B N3B C9B . . . . -0.6(7) ?
    C6B C1B C2B C3B . . . . -0.6(8) ?
    C1B C2B C3B C4B . . . . -0.3(8) ?
    C2B C3B C4B C5B . . . . 0.8(9) ?
    C3B C4B C5B C6B . . . . -0.4(8) ?
    C2B C1B C6B C5B . . . . 1.1(7) ?
    C2B C1B C6B C7B . . . . -177.7(5) ?
    C4B C5B C6B C1B . . . . -0.6(8) ?
    C4B C5B C6B C7B . . . . 178.2(4) ?
    N1B C7B C6B C1B . . . . 169.4(5) ?
    N1B C7B C6B C5B . . . . -9.3(8) ?
    C6B C7B N1B C8B . . . . -177.8(4) ?
    N3B N2B C8B N1B . . . . -179.9(4) ?
    N3B N2B C8B S1B . . . . 1.3(6) ?
    C7B N1B C8B N2B . . . . 152.7(5) ?
    C7B N1B C8B S1B . . . . -28.6(7) ?
    C9B S1B C8B N2B . . . . -1.2(5) ?
    C9B S1B C8B N1B . . . . -179.9(5) ?
    N2B N3B C9B C10B . . . . -179.1(4) ?
    N2B N3B C9B S1B . . . . -0.3(6) ?
    C8B S1B C9B N3B . . . . 0.8(4) ?
    C8B S1B C9B C10B . . . . 179.6(4) ?
    N3B C9B C10B C15B . . . . 161.7(5) ?
    S1B C9B C10B C15B . . . . -17.0(7) ?
    N3B C9B C10B C11B . . . . -17.8(7) ?
    S1B C9B C10B C11B . . . . 163.5(4) ?
    C15B C10B C11B C12B . . . . -0.4(7) ?
    C9B C10B C11B C12B . . . . 179.1(4) ?
    C10B C11B C12B C13B . . . . 1.1(7) ?
    C16B O1B C13B C14B . . . . 1.5(7) ?
    C16B O1B C13B C12B . . . . -179.3(5) ?
    C11B C12B C13B O1B . . . . 179.7(4) ?
    C11B C12B C13B C14B . . . . -1.1(8) ?
    O1B C13B C14B C15B . . . . 179.5(4) ?
    C12B C13B C14B C15B . . . . 0.4(7) ?
    C11B C10B C15B C14B . . . . -0.4(7) ?
    C9B C10B C15B C14B . . . . -179.9(4) ?
    C13B C14B C15B C10B . . . . 0.4(7) ?
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
    C7A H7A S1A . 0.93 2.73 3.121(5) 106 yes
    C7B H7B S1B . 0.93 2.72 3.124(5) 107 yes
    C16A H16B N3A 2_344 0.96 2.61 3.547(7) 164 yes
