# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2009

data_global
_journal_name_full               'New J.Chem.'

_journal_coden_Cambridge         0440
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dianzeng Jia'
_publ_contact_author_email       JDZ@XJU.EDU.CN

_publ_section_title              
;
Photo-switch and INHIBIT Logic Gate Based
on two Pyrazolone Thiosemicarbazone Derivatives
;
loop_
_publ_author_name
'Dianzeng Jia.'
'Jixi Guo.'
'Lang Liu.'
'Dongling Wu.'
'Xiaolin Xie.'
;
Xiangyun Xie
;

# Attachment '2.CIF'

data_2
_database_code_depnum_ccdc_archive 'CCDC 708004'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 F N5 O S'
_chemical_formula_weight         397.47

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.9254(3)
_cell_length_b                   13.0617(3)
_cell_length_c                   21.3133(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3876.66(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    36743
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      27.48

_exptl_crystal_description       chunk
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.57
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8908
_exptl_absorpt_correction_T_max  0.9252
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            34491
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4443
_reflns_number_gt                3898
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+1.8097P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4443
_refine_ls_number_parameters     269
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.68865(2) 0.57239(2) 0.674266(14) 0.02360(10) Uani 1 1 d . . .
F F 0.81429(7) 0.45241(6) 0.35507(4) 0.0358(2) Uani 1 1 d . . .
O O 0.65051(7) 0.38474(7) 0.52464(4) 0.0255(2) Uani 1 1 d . . .
N1 N 0.53669(8) 0.37265(8) 0.44539(5) 0.0215(2) Uani 1 1 d . . .
N2 N 0.52016(8) 0.42187(8) 0.38896(5) 0.0222(2) Uani 1 1 d D . .
N3 N 0.75109(7) 0.61311(8) 0.49746(4) 0.0196(2) Uani 1 1 d . . .
N4 N 0.70772(8) 0.57826(8) 0.55161(5) 0.0204(2) Uani 1 1 d D . .
N5 N 0.78775(8) 0.70577(8) 0.60400(5) 0.0231(2) Uani 1 1 d D . .
C1 C 0.48397(10) 0.24454(11) 0.51975(7) 0.0310(3) Uani 1 1 d . . .
H1 H 0.5049 0.2869 0.5533 0.037 Uiso 1 1 calc R . .
C2 C 0.44344(12) 0.14944(13) 0.53145(9) 0.0437(4) Uani 1 1 d . . .
H2 H 0.4378 0.1258 0.5734 0.052 Uiso 1 1 calc R . .
C3 C 0.41120(12) 0.08864(12) 0.48285(10) 0.0478(4) Uani 1 1 d . . .
H3 H 0.3838 0.0235 0.4915 0.057 Uiso 1 1 calc R . .
C4 C 0.41864(12) 0.12214(12) 0.42185(9) 0.0443(4) Uani 1 1 d . . .
H4 H 0.3950 0.0809 0.3886 0.053 Uiso 1 1 calc R . .
C5 C 0.46075(11) 0.21629(11) 0.40882(7) 0.0328(3) Uani 1 1 d . . .
H5 H 0.4671 0.2391 0.3667 0.039 Uiso 1 1 calc R . .
C6 C 0.49326(9) 0.27635(9) 0.45780(6) 0.0230(3) Uani 1 1 d . . .
C7 C 0.61488(9) 0.41730(9) 0.47466(5) 0.0197(2) Uani 1 1 d . . .
C8 C 0.64259(9) 0.50208(9) 0.43504(5) 0.0189(2) Uani 1 1 d . . .
C9 C 0.58088(9) 0.50090(9) 0.38391(5) 0.0200(2) Uani 1 1 d . . .
C10 C 0.57138(10) 0.56989(10) 0.32834(6) 0.0269(3) Uani 1 1 d . . .
H10A H 0.5056 0.5662 0.3121 0.032 Uiso 1 1 calc R . .
H10B H 0.6165 0.5483 0.2956 0.032 Uiso 1 1 calc R . .
H10C H 0.5858 0.6404 0.3408 0.032 Uiso 1 1 calc R . .
C11 C 0.72075(9) 0.57574(9) 0.44489(5) 0.0187(2) Uani 1 1 d . . .
C12 C 0.77109(9) 0.61792(9) 0.38884(5) 0.0200(2) Uani 1 1 d . . .
C13 C 0.81550(9) 0.55506(10) 0.34528(6) 0.0243(3) Uani 1 1 d . . .
C14 C 0.86183(10) 0.59092(11) 0.29247(6) 0.0300(3) Uani 1 1 d . . .
H14 H 0.8919 0.5451 0.2640 0.036 Uiso 1 1 calc R . .
C15 C 0.86317(10) 0.69587(11) 0.28217(6) 0.0312(3) Uani 1 1 d . . .
H15 H 0.8942 0.7227 0.2460 0.037 Uiso 1 1 calc R . .
C16 C 0.81962(10) 0.76131(11) 0.32425(6) 0.0296(3) Uani 1 1 d . . .
H16 H 0.8201 0.8330 0.3166 0.036 Uiso 1 1 calc R . .
C17 C 0.77502(9) 0.72340(10) 0.37772(6) 0.0242(3) Uani 1 1 d . . .
H17 H 0.7470 0.7694 0.4069 0.029 Uiso 1 1 calc R . .
C18 C 0.73307(9) 0.62364(9) 0.60669(5) 0.0195(2) Uani 1 1 d . . .
C19 C 0.81694(11) 0.76543(11) 0.65861(6) 0.0313(3) Uani 1 1 d . . .
H19A H 0.7612 0.7735 0.6870 0.038 Uiso 1 1 calc R . .
H19B H 0.8368 0.8346 0.6447 0.038 Uiso 1 1 calc R . .
C20 C 0.89844(13) 0.71672(14) 0.69435(8) 0.0463(4) Uani 1 1 d . . .
H20A H 0.9543 0.7097 0.6667 0.056 Uiso 1 1 calc R . .
H20B H 0.8787 0.6489 0.7092 0.056 Uiso 1 1 calc R . .
H20C H 0.9153 0.7598 0.7303 0.056 Uiso 1 1 calc R . .
H4N H 0.6863(11) 0.5158(8) 0.5510(8) 0.033(4) Uiso 1 1 d D . .
H5N H 0.8061(11) 0.7276(12) 0.5677(5) 0.030(4) Uiso 1 1 d D . .
H2N H 0.4634(8) 0.4173(14) 0.3725(8) 0.045(5) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.02821(18) 0.02594(17) 0.01664(15) 0.00210(11) -0.00222(11) -0.00738(12)
F 0.0505(5) 0.0205(4) 0.0364(5) -0.0007(3) 0.0060(4) 0.0032(4)
O 0.0360(5) 0.0200(4) 0.0206(4) 0.0050(3) -0.0074(4) -0.0037(4)
N1 0.0259(5) 0.0195(5) 0.0191(5) 0.0035(4) -0.0026(4) -0.0040(4)
N2 0.0236(5) 0.0229(5) 0.0202(5) 0.0038(4) -0.0050(4) -0.0027(4)
N3 0.0225(5) 0.0194(5) 0.0170(4) 0.0016(4) -0.0004(4) -0.0008(4)
N4 0.0246(5) 0.0197(5) 0.0170(5) 0.0001(4) -0.0007(4) -0.0049(4)
N5 0.0292(6) 0.0244(5) 0.0157(5) 0.0004(4) -0.0004(4) -0.0067(4)
C1 0.0295(7) 0.0303(7) 0.0333(7) 0.0074(6) 0.0039(6) -0.0033(6)
C2 0.0371(8) 0.0401(9) 0.0540(10) 0.0215(7) 0.0033(7) -0.0093(7)
C3 0.0338(8) 0.0284(7) 0.0811(13) 0.0174(8) -0.0042(8) -0.0122(6)
C4 0.0390(9) 0.0275(7) 0.0662(11) -0.0030(7) -0.0091(8) -0.0107(6)
C5 0.0336(7) 0.0262(7) 0.0387(7) -0.0002(6) -0.0032(6) -0.0071(6)
C6 0.0194(6) 0.0185(5) 0.0309(6) 0.0027(5) 0.0018(5) -0.0010(4)
C7 0.0241(6) 0.0167(5) 0.0182(5) -0.0007(4) -0.0014(5) 0.0001(4)
C8 0.0226(6) 0.0170(5) 0.0169(5) 0.0005(4) -0.0019(4) -0.0002(4)
C9 0.0223(6) 0.0189(5) 0.0187(5) 0.0004(4) -0.0012(4) -0.0005(4)
C10 0.0295(7) 0.0289(7) 0.0222(6) 0.0071(5) -0.0071(5) -0.0038(5)
C11 0.0213(6) 0.0160(5) 0.0187(5) 0.0009(4) -0.0021(4) 0.0008(4)
C12 0.0214(6) 0.0206(6) 0.0181(5) 0.0017(4) -0.0036(4) -0.0029(5)
C13 0.0285(7) 0.0207(6) 0.0236(6) -0.0001(5) -0.0027(5) -0.0006(5)
C14 0.0322(7) 0.0353(7) 0.0225(6) -0.0024(5) 0.0032(5) -0.0004(6)
C15 0.0308(7) 0.0388(8) 0.0239(6) 0.0065(5) 0.0020(5) -0.0083(6)
C16 0.0334(7) 0.0244(6) 0.0312(7) 0.0065(5) -0.0017(6) -0.0074(5)
C17 0.0278(6) 0.0206(6) 0.0243(6) 0.0005(5) -0.0025(5) -0.0035(5)
C18 0.0202(6) 0.0208(6) 0.0174(5) 0.0007(4) -0.0019(4) 0.0010(4)
C19 0.0438(8) 0.0270(7) 0.0231(6) -0.0044(5) -0.0003(6) -0.0149(6)
C20 0.0511(10) 0.0544(10) 0.0333(8) 0.0037(7) -0.0170(7) -0.0249(8)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C18 1.7044(12) . ?
F C13 1.3571(15) . ?
O C7 1.2498(14) . ?
N1 N2 1.3831(14) . ?
N1 C7 1.3838(16) . ?
N1 C6 1.4205(15) . ?
N2 C9 1.3386(16) . ?
N2 H2N 0.866(9) . ?
N3 C11 1.2930(15) . ?
N3 N4 1.3798(14) . ?
N4 C18 1.3616(15) . ?
N4 H4N 0.869(9) . ?
N5 C18 1.3169(16) . ?
N5 C19 1.4586(16) . ?
N5 H5N 0.863(9) . ?
C1 C2 1.387(2) . ?
C1 C6 1.3901(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3822(19) . ?
C5 H5 0.9500 . ?
C7 C8 1.4451(16) . ?
C8 C9 1.3879(16) . ?
C8 C11 1.4678(16) . ?
C9 C10 1.4941(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.4907(16) . ?
C12 C13 1.3852(18) . ?
C12 C17 1.3991(17) . ?
C13 C14 1.3793(19) . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3890(18) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 C20 1.508(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C7 109.09(9) . . ?
N2 N1 C6 120.19(10) . . ?
C7 N1 C6 128.62(10) . . ?
C9 N2 N1 108.86(10) . . ?
C9 N2 H2N 126.7(12) . . ?
N1 N2 H2N 118.1(13) . . ?
C11 N3 N4 117.21(10) . . ?
C18 N4 N3 117.65(10) . . ?
C18 N4 H4N 120.7(11) . . ?
N3 N4 H4N 116.6(11) . . ?
C18 N5 C19 124.17(10) . . ?
C18 N5 H5N 118.6(11) . . ?
C19 N5 H5N 117.1(11) . . ?
C2 C1 C6 118.44(14) . . ?
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
C3 C2 C1 120.85(15) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.12(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.12(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.29(15) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.15(12) . . ?
C5 C6 N1 120.09(12) . . ?
C1 C6 N1 118.76(12) . . ?
O C7 N1 123.59(11) . . ?
O C7 C8 130.75(11) . . ?
N1 C7 C8 105.64(10) . . ?
C9 C8 C7 106.55(10) . . ?
C9 C8 C11 125.37(10) . . ?
C7 C8 C11 128.08(10) . . ?
N2 C9 C8 109.67(10) . . ?
N2 C9 C10 118.22(11) . . ?
C8 C9 C10 132.10(11) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C8 127.86(11) . . ?
N3 C11 C12 113.66(10) . . ?
C8 C11 C12 118.44(10) . . ?
C13 C12 C17 116.92(11) . . ?
C13 C12 C11 121.88(11) . . ?
C17 C12 C11 121.20(11) . . ?
F C13 C14 117.82(12) . . ?
F C13 C12 118.49(11) . . ?
C14 C13 C12 123.68(12) . . ?
C13 C14 C15 118.07(13) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C16 C15 C14 120.21(12) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.60(13) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.50(12) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
N5 C18 N4 117.84(10) . . ?
N5 C18 S 124.51(9) . . ?
N4 C18 S 117.61(9) . . ?
N5 C19 C20 112.79(13) . . ?
N5 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
N5 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C9 -4.55(14) . . . . ?
C6 N1 N2 C9 -169.43(11) . . . . ?
C11 N3 N4 C18 -174.27(11) . . . . ?
C6 C1 C2 C3 -1.3(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 N1 179.84(13) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C2 C1 C6 N1 -178.59(13) . . . . ?
N2 N1 C6 C5 20.72(18) . . . . ?
C7 N1 C6 C5 -140.89(14) . . . . ?
N2 N1 C6 C1 -159.00(12) . . . . ?
C7 N1 C6 C1 39.39(19) . . . . ?
N2 N1 C7 O -175.30(11) . . . . ?
C6 N1 C7 O -12.1(2) . . . . ?
N2 N1 C7 C8 3.68(13) . . . . ?
C6 N1 C7 C8 166.91(12) . . . . ?
O C7 C8 C9 177.31(13) . . . . ?
N1 C7 C8 C9 -1.56(13) . . . . ?
O C7 C8 C11 -2.0(2) . . . . ?
N1 C7 C8 C11 179.12(11) . . . . ?
N1 N2 C9 C8 3.50(14) . . . . ?
N1 N2 C9 C10 -175.81(11) . . . . ?
C7 C8 C9 N2 -1.18(14) . . . . ?
C11 C8 C9 N2 178.17(11) . . . . ?
C7 C8 C9 C10 178.00(13) . . . . ?
C11 C8 C9 C10 -2.7(2) . . . . ?
N4 N3 C11 C8 2.16(18) . . . . ?
N4 N3 C11 C12 179.70(10) . . . . ?
C9 C8 C11 N3 145.67(13) . . . . ?
C7 C8 C11 N3 -35.1(2) . . . . ?
C9 C8 C11 C12 -31.77(17) . . . . ?
C7 C8 C11 C12 147.43(12) . . . . ?
N3 C11 C12 C13 125.05(13) . . . . ?
C8 C11 C12 C13 -57.17(16) . . . . ?
N3 C11 C12 C17 -55.34(16) . . . . ?
C8 C11 C12 C17 122.45(13) . . . . ?
C17 C12 C13 F 179.06(11) . . . . ?
C11 C12 C13 F -1.31(18) . . . . ?
C17 C12 C13 C14 -0.40(19) . . . . ?
C11 C12 C13 C14 179.23(12) . . . . ?
F C13 C14 C15 179.91(12) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C15 C16 C17 C12 -1.9(2) . . . . ?
C13 C12 C17 C16 1.64(19) . . . . ?
C11 C12 C17 C16 -177.99(12) . . . . ?
C19 N5 C18 N4 176.94(12) . . . . ?
C19 N5 C18 S -0.91(19) . . . . ?
N3 N4 C18 N5 8.34(17) . . . . ?
N3 N4 C18 S -173.65(8) . . . . ?
C18 N5 C19 C20 78.80(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N S 0.866(9) 2.345(10) 3.2057(11) 172.6(17) 5_666
N4 H4N O 0.869(9) 1.869(10) 2.7118(13) 163.0(16) .
N5 H5N O 0.863(9) 2.328(13) 3.0107(13) 136.2(14) 8_765

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042


# Attachment '1.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 708005'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19.50 H20 F N5 O1.50 S'
_chemical_formula_weight         399.46

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.4486(8)
_cell_length_b                   13.3331(9)
_cell_length_c                   21.6910(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3889.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    33359
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      25.25

_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1672
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9464
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            26179
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3519
_reflns_number_gt                2153
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0983P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0092(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3519
_refine_ls_number_parameters     272
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1748
_refine_ls_wR_factor_gt          0.1543
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.70487(6) 0.57729(6) 0.66822(4) 0.0586(3) Uani 1 1 d . . .
O1 O 0.65762(17) 0.39437(14) 0.52110(9) 0.0598(6) Uani 1 1 d . . .
F F 0.82297(16) 0.46859(14) 0.35373(10) 0.0799(6) Uani 1 1 d . . .
N1 N 0.53883(18) 0.37704(18) 0.44481(11) 0.0517(6) Uani 1 1 d . . .
N2 N 0.5192(2) 0.42434(19) 0.38924(12) 0.0532(7) Uani 1 1 d D . .
N3 N 0.75492(18) 0.62058(18) 0.49303(11) 0.0494(6) Uani 1 1 d . . .
N4 N 0.71516(18) 0.58398(19) 0.54724(11) 0.0489(6) Uani 1 1 d D . .
N5 N 0.7867(2) 0.7174(2) 0.59636(12) 0.0588(7) Uani 1 1 d D . .
C1 C 0.4870(2) 0.2534(2) 0.51913(16) 0.0626(9) Uani 1 1 d . . .
H1 H 0.5054 0.2968 0.5507 0.075 Uiso 1 1 calc R . .
C2 C 0.4486(3) 0.1592(3) 0.5323(2) 0.0818(12) Uani 1 1 d . . .
H2 H 0.4424 0.1387 0.5731 0.098 Uiso 1 1 calc R . .
C3 C 0.4197(3) 0.0963(3) 0.4857(3) 0.0883(13) Uani 1 1 d . . .
H3 H 0.3937 0.0334 0.4950 0.106 Uiso 1 1 calc R . .
C4 C 0.4290(3) 0.1254(3) 0.4260(2) 0.0863(12) Uani 1 1 d . . .
H4 H 0.4082 0.0826 0.3947 0.104 Uiso 1 1 calc R . .
C5 C 0.4691(2) 0.2184(3) 0.41121(18) 0.0696(10) Uani 1 1 d . . .
H5 H 0.4767 0.2375 0.3702 0.083 Uiso 1 1 calc R . .
C6 C 0.4975(2) 0.2815(2) 0.45792(15) 0.0524(8) Uani 1 1 d . . .
C7 C 0.6185(2) 0.4247(2) 0.47220(13) 0.0479(7) Uani 1 1 d . . .
C8 C 0.6435(2) 0.5080(2) 0.43305(13) 0.0457(7) Uani 1 1 d . . .
C9 C 0.5784(2) 0.5040(2) 0.38332(13) 0.0490(7) Uani 1 1 d . . .
C10 C 0.5643(2) 0.5696(2) 0.32832(14) 0.0615(9) Uani 1 1 d . . .
H10A H 0.6113 0.5513 0.2970 0.074 Uiso 1 1 calc R . .
H10B H 0.5745 0.6383 0.3398 0.074 Uiso 1 1 calc R . .
H10C H 0.4980 0.5614 0.3127 0.074 Uiso 1 1 calc R . .
C11 C 0.7220(2) 0.5833(2) 0.44190(13) 0.0455(7) Uani 1 1 d . . .
C12 C 0.7694(2) 0.6277(2) 0.38615(13) 0.0469(7) Uani 1 1 d . . .
C13 C 0.8175(2) 0.5697(2) 0.34318(15) 0.0564(8) Uani 1 1 d . . .
C14 C 0.8608(3) 0.6063(3) 0.29073(16) 0.0677(9) Uani 1 1 d . . .
H14 H 0.8928 0.5639 0.2630 0.081 Uiso 1 1 calc R . .
C15 C 0.8553(3) 0.7078(3) 0.28041(16) 0.0704(10) Uani 1 1 d . . .
H15 H 0.8829 0.7349 0.2448 0.084 Uiso 1 1 calc R . .
C16 C 0.8096(3) 0.7694(3) 0.32222(16) 0.0656(9) Uani 1 1 d . . .
H16 H 0.8070 0.8381 0.3150 0.079 Uiso 1 1 calc R . .
C17 C 0.7675(2) 0.7302(2) 0.37484(15) 0.0566(8) Uani 1 1 d . . .
H17 H 0.7374 0.7729 0.4031 0.068 Uiso 1 1 calc R . .
C18 C 0.7400(2) 0.6310(2) 0.60071(13) 0.0470(7) Uani 1 1 d . . .
C19 C 0.8130(3) 0.7801(3) 0.64801(16) 0.0840(12) Uani 1 1 d . . .
H19A H 0.7859 0.7521 0.6852 0.101 Uiso 1 1 calc R . .
H19B H 0.7866 0.8462 0.6418 0.101 Uiso 1 1 calc R . .
H19C H 0.8841 0.7837 0.6514 0.101 Uiso 1 1 calc R . .
H2N H 0.4623(12) 0.421(2) 0.3718(13) 0.056(9) Uiso 1 1 d D . .
H4N H 0.693(2) 0.5233(11) 0.5485(14) 0.055(9) Uiso 1 1 d D . .
H5N H 0.804(2) 0.738(2) 0.5610(7) 0.047(8) Uiso 1 1 d D . .
C20 C 1.0000 0.6611(10) 0.7500 0.258(10) Uani 1 2 d S . .
O2 O 0.9589(8) 0.5921(9) 0.7071(7) 0.211(5) Uani 0.50 1 d P . .
H2A H 0.9062 0.6142 0.6938 0.253 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.0712(6) 0.0565(6) 0.0481(5) 0.0039(4) -0.0040(4) -0.0117(4)
O1 0.0791(15) 0.0439(13) 0.0562(13) 0.0089(10) -0.0153(11) -0.0054(11)
F 0.1019(15) 0.0479(12) 0.0900(15) -0.0005(10) 0.0238(12) 0.0098(10)
N1 0.0602(15) 0.0434(15) 0.0514(15) 0.0074(11) -0.0030(12) -0.0078(12)
N2 0.0556(16) 0.0526(16) 0.0514(16) 0.0047(12) -0.0101(13) -0.0062(13)
N3 0.0526(15) 0.0458(15) 0.0498(14) 0.0028(12) 0.0003(12) -0.0013(11)
N4 0.0588(15) 0.0395(15) 0.0485(15) 0.0006(11) -0.0008(12) -0.0066(12)
N5 0.0762(18) 0.0520(17) 0.0482(16) -0.0015(12) 0.0044(14) -0.0193(14)
C1 0.0617(19) 0.054(2) 0.073(2) 0.0073(17) 0.0077(17) -0.0008(15)
C2 0.069(2) 0.064(3) 0.112(3) 0.033(2) 0.012(2) -0.004(2)
C3 0.065(2) 0.052(2) 0.148(4) 0.022(3) -0.001(3) -0.0106(18)
C4 0.075(3) 0.056(2) 0.128(4) -0.011(2) -0.010(3) -0.015(2)
C5 0.069(2) 0.054(2) 0.086(3) -0.0058(18) -0.0043(19) -0.0156(17)
C6 0.0489(16) 0.0408(17) 0.067(2) 0.0024(15) 0.0049(15) -0.0018(13)
C7 0.0539(17) 0.0372(16) 0.0525(18) -0.0021(13) -0.0030(15) -0.0018(13)
C8 0.0544(17) 0.0353(16) 0.0473(17) 0.0045(12) -0.0018(14) 0.0018(13)
C9 0.0547(17) 0.0454(17) 0.0468(17) 0.0037(12) -0.0007(15) -0.0006(14)
C10 0.064(2) 0.065(2) 0.0550(19) 0.0128(15) -0.0109(16) -0.0070(16)
C11 0.0535(17) 0.0355(16) 0.0474(16) 0.0018(12) -0.0038(14) 0.0022(13)
C12 0.0520(17) 0.0406(17) 0.0481(16) 0.0014(13) -0.0050(14) -0.0047(13)
C13 0.068(2) 0.0390(18) 0.063(2) 0.0049(14) 0.0023(16) -0.0012(14)
C14 0.078(2) 0.064(2) 0.061(2) -0.0029(17) 0.0130(18) -0.0013(18)
C15 0.079(2) 0.073(3) 0.059(2) 0.0161(18) 0.0043(18) -0.0093(19)
C16 0.077(2) 0.049(2) 0.071(2) 0.0134(17) -0.0027(18) -0.0085(17)
C17 0.066(2) 0.0450(19) 0.0588(19) 0.0049(14) -0.0038(16) -0.0032(15)
C18 0.0492(16) 0.0461(18) 0.0459(16) 0.0000(13) -0.0053(13) 0.0004(13)
C19 0.112(3) 0.074(3) 0.066(2) -0.0133(19) 0.003(2) -0.042(2)
C20 0.38(2) 0.154(12) 0.242(16) 0.000 -0.187(16) 0.000
O2 0.151(9) 0.215(12) 0.267(14) 0.071(10) 0.050(8) 0.064(8)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C18 1.697(3) . ?
O1 C7 1.251(3) . ?
F C13 1.369(3) . ?
N1 C7 1.381(4) . ?
N1 N2 1.386(3) . ?
N1 C6 1.419(4) . ?
N2 C9 1.334(4) . ?
N2 H2N 0.855(10) . ?
N3 C11 1.293(3) . ?
N3 N4 1.381(3) . ?
N4 C18 1.360(4) . ?
N4 H4N 0.864(10) . ?
N5 C18 1.316(4) . ?
N5 C19 1.442(4) . ?
N5 H5N 0.850(10) . ?
C1 C2 1.387(5) . ?
C1 C6 1.387(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.438(4) . ?
C8 C9 1.390(4) . ?
C8 C11 1.470(4) . ?
C9 C10 1.491(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.489(4) . ?
C12 C13 1.373(4) . ?
C12 C17 1.388(4) . ?
C13 C14 1.368(4) . ?
C14 C15 1.374(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O2 1.421(15) 3_756 ?
C20 O2 1.421(15) . ?
O2 H2A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 N2 108.2(2) . . ?
C7 N1 C6 129.2(3) . . ?
N2 N1 C6 120.6(2) . . ?
C9 N2 N1 109.4(2) . . ?
C9 N2 H2N 122(2) . . ?
N1 N2 H2N 122(2) . . ?
C11 N3 N4 117.5(2) . . ?
C18 N4 N3 117.9(2) . . ?
C18 N4 H4N 119(2) . . ?
N3 N4 H4N 120(2) . . ?
C18 N5 C19 124.7(3) . . ?
C18 N5 H5N 119(2) . . ?
C19 N5 H5N 116(2) . . ?
C2 C1 C6 118.7(4) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 N1 120.8(3) . . ?
C1 C6 N1 118.3(3) . . ?
O1 C7 N1 122.8(3) . . ?
O1 C7 C8 130.8(3) . . ?
N1 C7 C8 106.4(2) . . ?
C9 C8 C7 106.4(2) . . ?
C9 C8 C11 125.5(2) . . ?
C7 C8 C11 128.2(2) . . ?
N2 C9 C8 109.4(2) . . ?
N2 C9 C10 117.9(3) . . ?
C8 C9 C10 132.7(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C8 128.3(3) . . ?
N3 C11 C12 113.4(3) . . ?
C8 C11 C12 118.2(2) . . ?
C13 C12 C17 116.3(3) . . ?
C13 C12 C11 121.9(3) . . ?
C17 C12 C11 121.8(3) . . ?
C14 C13 F 117.8(3) . . ?
C14 C13 C12 124.4(3) . . ?
F C13 C12 117.8(3) . . ?
C13 C14 C15 117.6(3) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
N5 C18 N4 117.3(3) . . ?
N5 C18 S 124.3(2) . . ?
N4 C18 S 118.3(2) . . ?
N5 C19 H19A 109.5 . . ?
N5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 O2 99.3(14) 3_756 . ?
C20 O2 H2A 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C9 -4.8(3) . . . . ?
C6 N1 N2 C9 -169.8(3) . . . . ?
C11 N3 N4 C18 -172.0(3) . . . . ?
C6 C1 C2 C3 -1.4(5) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C4 C5 C6 N1 180.0(3) . . . . ?
C2 C1 C6 C5 1.0(5) . . . . ?
C2 C1 C6 N1 -178.6(3) . . . . ?
C7 N1 C6 C5 -137.8(3) . . . . ?
N2 N1 C6 C5 23.8(4) . . . . ?
C7 N1 C6 C1 41.9(4) . . . . ?
N2 N1 C6 C1 -156.5(3) . . . . ?
N2 N1 C7 O1 -175.1(3) . . . . ?
C6 N1 C7 O1 -11.7(5) . . . . ?
N2 N1 C7 C8 3.7(3) . . . . ?
C6 N1 C7 C8 167.1(3) . . . . ?
O1 C7 C8 C9 177.2(3) . . . . ?
N1 C7 C8 C9 -1.4(3) . . . . ?
O1 C7 C8 C11 -2.3(5) . . . . ?
N1 C7 C8 C11 179.1(3) . . . . ?
N1 N2 C9 C8 3.9(3) . . . . ?
N1 N2 C9 C10 -175.9(3) . . . . ?
C7 C8 C9 N2 -1.5(3) . . . . ?
C11 C8 C9 N2 178.0(3) . . . . ?
C7 C8 C9 C10 178.3(3) . . . . ?
C11 C8 C9 C10 -2.2(5) . . . . ?
N4 N3 C11 C8 2.5(4) . . . . ?
N4 N3 C11 C12 180.0(2) . . . . ?
C9 C8 C11 N3 147.0(3) . . . . ?
C7 C8 C11 N3 -33.6(5) . . . . ?
C9 C8 C11 C12 -30.4(4) . . . . ?
C7 C8 C11 C12 149.1(3) . . . . ?
N3 C11 C12 C13 123.3(3) . . . . ?
C8 C11 C12 C13 -59.0(4) . . . . ?
N3 C11 C12 C17 -56.6(4) . . . . ?
C8 C11 C12 C17 121.1(3) . . . . ?
C17 C12 C13 C14 -1.2(5) . . . . ?
C11 C12 C13 C14 178.9(3) . . . . ?
C17 C12 C13 F 178.3(3) . . . . ?
C11 C12 C13 F -1.5(4) . . . . ?
F C13 C14 C15 -179.8(3) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C16 1.3(5) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 C12 -0.8(5) . . . . ?
C13 C12 C17 C16 1.7(5) . . . . ?
C11 C12 C17 C16 -178.4(3) . . . . ?
C19 N5 C18 N4 176.0(3) . . . . ?
C19 N5 C18 S -1.4(5) . . . . ?
N3 N4 C18 N5 10.8(4) . . . . ?
N3 N4 C18 S -171.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N S 0.855(10) 2.410(11) 3.261(3) 174(3) 5_666
N4 H4N O1 0.864(10) 1.879(14) 2.704(3) 159(3) .
N5 H5N O1 0.850(10) 2.31(2) 2.966(3) 134(3) 8_765
O2 H2A S 0.82 2.81 3.524(12) 147.1 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.067