##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-05-11
_journal_date_accepted     2010-05-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1446
_journal_page_last     o1447
_journal_paper_category     QO
_journal_coeditor_code     TK2674
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;\
3-{2-[2-(2-Fluorobenzylidene)hydrazinyl]-1,3-thiazol-4-yl}-2<i>H</i>-chromen-2-\
one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Afsheen Arshad' ?
;
        School of Chemical Sciences
        Universiti Sains Malaysia
        11800 USM, Penang
        Malaysia
;
    'Hasnah Osman'
;
        Additional correspondence author, e-mail: ohasnah@usm.my.
;
;
        School of Chemical Sciences
        Universiti Sains Malaysia
        11800 USM, Penang
        Malaysia
;
    'Chan Kit Lam' ?
;
      School of Pharmaceutical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Ching Kheng Quah'
;
      Thomson Reuters ResearcherID: A-5525-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-{2-[2-(2-Fluorobenzylidene)hydrazinyl]-1,3-thiazol-4-yl}-
2<i>H</i>-chromen-2-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H12 F N3 O2 S'
_chemical_formula_sum     'C19 H12 F N3 O2 S'
_chemical_formula_iupac     'C19 H12 F N3 O2 S'
_chemical_formula_weight     365.38
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P b c n'
_symmetry_space_group_name_Hall     '-P 2n 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y, z-1/2'
_cell_length_a     12.303(2)
_cell_length_b     10.4477(17)
_cell_length_c     25.247(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3245.2(9)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     1466
_cell_measurement_theta_min     3.23
_cell_measurement_theta_max     27.10
_cell_measurement_temperature     100
_exptl_crystal_description     'needle'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.374
_exptl_crystal_size_mid     0.077
_exptl_crystal_size_min     0.039
_exptl_crystal_density_diffrn     1.496
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1504
_exptl_absorpt_coefficient_mu     0.230
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(<i>SADABS</i>; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9189
_exptl_absorpt_correction_T_max     0.9911
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
;
_diffrn_ambient_temperature     100
_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
;
Bruker SMART APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13589
_diffrn_reflns_av_R_equivalents     0.0822
_diffrn_reflns_av_sigmaI/netI     0.0620
_diffrn_reflns_theta_min     1.61
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     30
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
wR and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. <i>R</i>-factors
based on <i>F</i>^2^ are statistically about twice as large as those based on
<i>F</i>, and <i>R</i>- factors based on ALL data will be even larger.
;
_reflns_number_total     2855
_reflns_number_gt     1971
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0766
_refine_ls_R_factor_gt     0.0435
_refine_ls_wR_factor_gt     0.0874
_refine_ls_wR_factor_ref     0.1021
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     2855
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.4898P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.220
_refine_diff_density_min     -0.326
_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'
    'F' 'F' 0.0171 0.0103
                         '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     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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 0.88953(5) 0.06999(6) 0.02651(3) 0.02149(19) Uani d . 1 . .
    F F1 0.54027(12) -0.24735(15) 0.18957(7) 0.0376(5) Uani d . 1 . .
    O O1 0.85525(13) 0.52077(17) -0.12371(7) 0.0230(5) Uani d . 1 . .
    O O2 0.97044(14) 0.41533(18) -0.07423(8) 0.0309(5) Uani d . 1 . .
    N N1 0.72862(17) -0.0844(2) 0.07751(9) 0.0205(5) Uani d . 1 . .
    N N2 0.68221(19) 0.0019(2) 0.04366(9) 0.0211(5) Uani d . 1 . .
    N N3 0.71706(16) 0.17627(19) -0.01285(9) 0.0179(5) Uani d . 1 . .
    C C1 0.8140(2) -0.2887(2) 0.14056(11) 0.0225(6) Uani d . 1 . .
    H H1 0.8600 -0.2571 0.1144 0.027 Uiso calc R 1 . .
    C C2 0.8520(2) -0.3806(2) 0.17528(11) 0.0244(7) Uani d . 1 . .
    H H2 0.9232 -0.4097 0.1725 0.029 Uiso calc R 1 . .
    C C3 0.7845(2) -0.4299(3) 0.21429(11) 0.0293(7) Uani d . 1 . .
    H H3 0.8099 -0.4933 0.2370 0.035 Uiso calc R 1 . .
    C C4 0.6792(2) -0.3843(3) 0.21930(11) 0.0296(7) Uani d . 1 . .
    H H4 0.6334 -0.4155 0.2456 0.035 Uiso calc R 1 . .
    C C5 0.6442(2) -0.2922(3) 0.18451(12) 0.0258(7) Uani d . 1 . .
    C C6 0.7077(2) -0.2424(2) 0.14401(11) 0.0214(6) Uani d . 1 . .
    C C7 0.6640(2) -0.1475(2) 0.10749(11) 0.0210(6) Uani d . 1 . .
    H H7 0.5895 -0.1329 0.1060 0.025 Uiso calc R 1 . .
    C C8 0.7499(2) 0.0851(2) 0.01854(10) 0.0181(6) Uani d . 1 . .
    C C9 0.9051(2) 0.1990(2) -0.01532(11) 0.0216(6) Uani d . 1 . .
    H H9 0.9717 0.2340 -0.0250 0.026 Uiso calc R 1 . .
    C C10 0.80743(19) 0.2424(2) -0.03219(10) 0.0169(6) Uani d . 1 . .
    C C11 0.78532(19) 0.3487(2) -0.06865(11) 0.0176(6) Uani d . 1 . .
    C C12 0.6839(2) 0.3765(2) -0.08582(10) 0.0181(6) Uani d . 1 . .
    H H12 0.6256 0.3283 -0.0735 0.022 Uiso calc R 1 . .
    C C13 0.6639(2) 0.4783(2) -0.12245(11) 0.0197(6) Uani d . 1 . .
    C C14 0.5599(2) 0.5110(3) -0.14162(11) 0.0225(6) Uani d . 1 . .
    H H14 0.4993 0.4657 -0.1300 0.027 Uiso calc R 1 . .
    C C15 0.5474(2) 0.6092(2) -0.17731(11) 0.0244(7) Uani d . 1 . .
    H H15 0.4785 0.6302 -0.1897 0.029 Uiso calc R 1 . .
    C C16 0.6378(2) 0.6774(3) -0.19495(11) 0.0264(7) Uani d . 1 . .
    H H16 0.6288 0.7433 -0.2193 0.032 Uiso calc R 1 . .
    C C17 0.7405(2) 0.6480(2) -0.17669(11) 0.0243(7) Uani d . 1 . .
    H H17 0.8008 0.6940 -0.1881 0.029 Uiso calc R 1 . .
    C C18 0.7515(2) 0.5489(2) -0.14105(11) 0.0197(6) Uani d . 1 . .
    C C19 0.8764(2) 0.4266(2) -0.08730(11) 0.0206(6) Uani d . 1 . .
    H H12N 0.615(2) 0.019(3) 0.0458(11) 0.030(8) Uiso d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0159(3) 0.0227(4) 0.0259(4) 0.0030(3) -0.0001(3) 0.0013(3)
    F1 0.0327(10) 0.0392(10) 0.0409(12) -0.0040(8) 0.0141(8) 0.0027(9)
    O1 0.0179(10) 0.0250(10) 0.0261(12) -0.0044(8) 0.0005(8) 0.0017(9)
    O2 0.0147(10) 0.0368(11) 0.0413(14) -0.0049(9) -0.0028(9) 0.0075(10)
    N1 0.0232(12) 0.0150(11) 0.0233(14) 0.0024(10) 0.0011(10) -0.0016(10)
    N2 0.0160(12) 0.0197(12) 0.0277(15) 0.0023(11) 0.0025(10) 0.0032(11)
    N3 0.0142(11) 0.0176(11) 0.0219(14) 0.0009(9) 0.0013(9) 0.0004(10)
    C1 0.0245(15) 0.0192(13) 0.0237(17) -0.0059(12) 0.0010(12) -0.0045(13)
    C2 0.0299(16) 0.0183(14) 0.0251(18) -0.0026(12) -0.0030(13) -0.0016(13)
    C3 0.0457(19) 0.0181(14) 0.0240(18) -0.0078(14) -0.0051(13) 0.0032(14)
    C4 0.0436(19) 0.0239(15) 0.0212(18) -0.0147(14) 0.0058(14) 0.0001(13)
    C5 0.0262(16) 0.0240(15) 0.0273(18) -0.0067(13) 0.0053(13) -0.0072(14)
    C6 0.0290(15) 0.0144(13) 0.0207(17) -0.0052(12) 0.0006(12) -0.0050(12)
    C7 0.0242(15) 0.0159(13) 0.0228(17) -0.0007(12) 0.0038(12) -0.0051(12)
    C8 0.0171(13) 0.0158(12) 0.0213(16) 0.0024(11) -0.0012(11) -0.0051(12)
    C9 0.0170(14) 0.0227(14) 0.0252(17) 0.0010(12) 0.0042(12) -0.0024(12)
    C10 0.0148(13) 0.0177(12) 0.0183(15) -0.0012(11) -0.0001(11) -0.0049(12)
    C11 0.0165(14) 0.0175(13) 0.0189(16) -0.0013(11) 0.0017(11) -0.0044(12)
    C12 0.0153(13) 0.0189(13) 0.0202(16) -0.0009(11) 0.0040(11) -0.0034(12)
    C13 0.0218(15) 0.0182(13) 0.0191(16) 0.0009(11) 0.0026(11) -0.0040(12)
    C14 0.0219(15) 0.0242(15) 0.0215(17) 0.0026(12) 0.0023(12) -0.0015(13)
    C15 0.0263(16) 0.0250(15) 0.0220(18) 0.0087(13) -0.0023(12) -0.0016(13)
    C16 0.0399(18) 0.0188(14) 0.0206(18) 0.0042(13) -0.0005(13) 0.0003(13)
    C17 0.0310(16) 0.0208(14) 0.0210(17) -0.0051(13) 0.0027(13) -0.0020(13)
    C18 0.0211(14) 0.0175(13) 0.0206(16) 0.0002(11) 0.0007(12) -0.0051(12)
    C19 0.0214(15) 0.0183(13) 0.0222(16) -0.0009(12) -0.0004(11) -0.0010(13)
_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 C9 . 1.723(3) ?
    S1 C8 . 1.736(2) ?
    F1 C5 . 1.367(3) ?
    O1 C19 . 1.372(3) ?
    O1 C18 . 1.381(3) ?
    O2 C19 . 1.209(3) ?
    N1 C7 . 1.281(3) ?
    N1 N2 . 1.368(3) ?
    N2 C8 . 1.361(3) ?
    N2 H12N . 0.85(3) ?
    N3 C8 . 1.303(3) ?
    N3 C10 . 1.397(3) ?
    C1 C2 . 1.382(4) ?
    C1 C6 . 1.397(4) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.387(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.386(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.372(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.388(4) ?
    C6 C7 . 1.456(4) ?
    C7 H7 . 0.9300 ?
    C9 C10 . 1.354(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.469(4) ?
    C11 C12 . 1.353(3) ?
    C11 C19 . 1.462(4) ?
    C12 C13 . 1.431(4) ?
    C12 H12 . 0.9300 ?
    C13 C18 . 1.387(4) ?
    C13 C14 . 1.410(4) ?
    C14 C15 . 1.374(4) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.394(4) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.379(4) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.379(4) ?
    C17 H17 . 0.9300 ?
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 C8 . . 88.17(12) ?
    C19 O1 C18 . . 122.7(2) ?
    C7 N1 N2 . . 116.7(2) ?
    C8 N2 N1 . . 117.2(2) ?
    C8 N2 H12N . . 119.4(19) ?
    N1 N2 H12N . . 121(2) ?
    C8 N3 C10 . . 109.1(2) ?
    C2 C1 C6 . . 121.2(3) ?
    C2 C1 H1 . . 119.4 ?
    C6 C1 H1 . . 119.4 ?
    C1 C2 C3 . . 120.4(3) ?
    C1 C2 H2 . . 119.8 ?
    C3 C2 H2 . . 119.8 ?
    C4 C3 C2 . . 119.8(3) ?
    C4 C3 H3 . . 120.1 ?
    C2 C3 H3 . . 120.1 ?
    C5 C4 C3 . . 118.4(3) ?
    C5 C4 H4 . . 120.8 ?
    C3 C4 H4 . . 120.8 ?
    F1 C5 C4 . . 118.3(2) ?
    F1 C5 C6 . . 117.8(3) ?
    C4 C5 C6 . . 123.9(3) ?
    C5 C6 C1 . . 116.3(3) ?
    C5 C6 C7 . . 120.9(2) ?
    C1 C6 C7 . . 122.8(3) ?
    N1 C7 C6 . . 119.7(2) ?
    N1 C7 H7 . . 120.2 ?
    C6 C7 H7 . . 120.2 ?
    N3 C8 N2 . . 124.1(2) ?
    N3 C8 S1 . . 116.36(19) ?
    N2 C8 S1 . . 119.6(2) ?
    C10 C9 S1 . . 110.85(19) ?
    C10 C9 H9 . . 124.6 ?
    S1 C9 H9 . . 124.6 ?
    C9 C10 N3 . . 115.5(2) ?
    C9 C10 C11 . . 128.0(2) ?
    N3 C10 C11 . . 116.5(2) ?
    C12 C11 C19 . . 119.0(2) ?
    C12 C11 C10 . . 122.3(2) ?
    C19 C11 C10 . . 118.7(2) ?
    C11 C12 C13 . . 121.7(2) ?
    C11 C12 H12 . . 119.2 ?
    C13 C12 H12 . . 119.2 ?
    C18 C13 C14 . . 117.4(2) ?
    C18 C13 C12 . . 118.7(2) ?
    C14 C13 C12 . . 123.9(2) ?
    C15 C14 C13 . . 120.5(2) ?
    C15 C14 H14 . . 119.8 ?
    C13 C14 H14 . . 119.8 ?
    C14 C15 C16 . . 120.1(2) ?
    C14 C15 H15 . . 120.0 ?
    C16 C15 H15 . . 120.0 ?
    C17 C16 C15 . . 120.7(3) ?
    C17 C16 H16 . . 119.6 ?
    C15 C16 H16 . . 119.6 ?
    C16 C17 C18 . . 118.4(3) ?
    C16 C17 H17 . . 120.8 ?
    C18 C17 H17 . . 120.8 ?
    C17 C18 O1 . . 117.2(2) ?
    C17 C18 C13 . . 122.9(2) ?
    O1 C18 C13 . . 119.8(2) ?
    O2 C19 O1 . . 115.7(2) ?
    O2 C19 C11 . . 126.3(2) ?
    O1 C19 C11 . . 118.0(2) ?
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
    C7 N1 N2 C8 . . . . 168.7(2) ?
    C6 C1 C2 C3 . . . . 0.5(4) ?
    C1 C2 C3 C4 . . . . -1.6(4) ?
    C2 C3 C4 C5 . . . . 1.0(4) ?
    C3 C4 C5 F1 . . . . -179.9(2) ?
    C3 C4 C5 C6 . . . . 0.7(4) ?
    F1 C5 C6 C1 . . . . 178.9(2) ?
    C4 C5 C6 C1 . . . . -1.7(4) ?
    F1 C5 C6 C7 . . . . -1.3(4) ?
    C4 C5 C6 C7 . . . . 178.1(2) ?
    C2 C1 C6 C5 . . . . 1.0(4) ?
    C2 C1 C6 C7 . . . . -178.7(2) ?
    N2 N1 C7 C6 . . . . 179.2(2) ?
    C5 C6 C7 N1 . . . . 166.1(2) ?
    C1 C6 C7 N1 . . . . -14.2(4) ?
    C10 N3 C8 N2 . . . . -179.4(2) ?
    C10 N3 C8 S1 . . . . -0.9(3) ?
    N1 N2 C8 N3 . . . . -176.7(2) ?
    N1 N2 C8 S1 . . . . 4.9(3) ?
    C9 S1 C8 N3 . . . . 0.9(2) ?
    C9 S1 C8 N2 . . . . 179.4(2) ?
    C8 S1 C9 C10 . . . . -0.5(2) ?
    S1 C9 C10 N3 . . . . 0.1(3) ?
    S1 C9 C10 C11 . . . . -179.0(2) ?
    C8 N3 C10 C9 . . . . 0.5(3) ?
    C8 N3 C10 C11 . . . . 179.7(2) ?
    C9 C10 C11 C12 . . . . 174.6(3) ?
    N3 C10 C11 C12 . . . . -4.5(4) ?
    C9 C10 C11 C19 . . . . -4.9(4) ?
    N3 C10 C11 C19 . . . . 176.0(2) ?
    C19 C11 C12 C13 . . . . 1.2(4) ?
    C10 C11 C12 C13 . . . . -178.3(2) ?
    C11 C12 C13 C18 . . . . 0.7(4) ?
    C11 C12 C13 C14 . . . . 179.9(2) ?
    C18 C13 C14 C15 . . . . 0.0(4) ?
    C12 C13 C14 C15 . . . . -179.2(3) ?
    C13 C14 C15 C16 . . . . 0.1(4) ?
    C14 C15 C16 C17 . . . . -0.5(4) ?
    C15 C16 C17 C18 . . . . 0.7(4) ?
    C16 C17 C18 O1 . . . . 179.5(2) ?
    C16 C17 C18 C13 . . . . -0.6(4) ?
    C19 O1 C18 C17 . . . . 178.3(2) ?
    C19 O1 C18 C13 . . . . -1.6(4) ?
    C14 C13 C18 C17 . . . . 0.3(4) ?
    C12 C13 C18 C17 . . . . 179.5(2) ?
    C14 C13 C18 O1 . . . . -179.8(2) ?
    C12 C13 C18 O1 . . . . -0.6(4) ?
    C18 O1 C19 O2 . . . . -177.4(2) ?
    C18 O1 C19 C11 . . . . 3.5(3) ?
    C12 C11 C19 O2 . . . . 177.7(3) ?
    C10 C11 C19 O2 . . . . -2.7(4) ?
    C12 C11 C19 O1 . . . . -3.3(4) ?
    C10 C11 C19 O1 . . . . 176.3(2) ?
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
    C9 H9 O2 . 0.9300 2.2700 2.823(3) 118.00 yes
    N2 H12N O2 3_455 0.85(3) 2.04(3) 2.852(3) 161(3) yes
    C4 H4 Cg1 8_555 0.9300 2.96 3.701(3) 138 yes