# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wjj2
_database_code_depnum_ccdc_archive 'CCDC 850784'
_audit_update_record             
;
2011-10-26 deposited with the CCDC.
2015-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 F N5 O S'
_chemical_formula_sum            'C19 H16 F N5 O S'
_chemical_formula_weight         381.43

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0942(9)
_cell_length_b                   11.4047(11)
_cell_length_c                   17.1200(16)
_cell_angle_alpha                108.2430(10)
_cell_angle_beta                 95.5870(10)
_cell_angle_gamma                98.5010(10)
_cell_volume                     1829.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2590
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9389
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_process_details   '(SADABS; Bruker 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17389
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         28.23
_reflns_number_total             8814
_reflns_number_gt                4531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.0243P] where P=(Fo²+2Fc²)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8814
_refine_ls_number_parameters     493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1013
_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
S1 S 0.73949(7) 0.21326(6) 0.43355(4) 0.0515(2) Uani 1 1 d . . .
S2 S 0.07289(7) -0.20739(6) 1.19780(4) 0.0529(2) Uani 1 1 d . . .
O1 O 0.52516(18) 0.03450(15) 0.74944(10) 0.0536(5) Uani 1 1 d . . .
O2 O 0.29561(17) -0.00476(14) 0.89275(9) 0.0506(5) Uani 1 1 d . . .
F1 F 0.32593(17) 0.47391(14) 0.91957(9) 0.0748(5) Uani 1 1 d . . .
F2 F 0.50048(19) -0.44168(15) 0.71899(11) 0.0945(6) Uani 1 1 d . . .
C1 C 0.7235(2) 0.1004(2) 0.48299(13) 0.0368(5) Uani 1 1 d . . .
C2 C 0.6622(2) 0.1104(2) 0.55503(12) 0.0357(5) Uani 1 1 d . . .
C3 C 0.6084(2) 0.2075(2) 0.61184(13) 0.0377(5) Uani 1 1 d . . .
C4 C 0.5740(2) 0.0517(2) 0.68325(13) 0.0396(6) Uani 1 1 d . . .
C5 C 0.6685(2) -0.0005(2) 0.57003(13) 0.0359(5) Uani 1 1 d . . .
C6 C 0.7656(3) -0.1910(2) 0.49974(13) 0.0413(6) Uani 1 1 d . . .
C7 C 0.6817(3) -0.2819(2) 0.51902(15) 0.0552(7) Uani 1 1 d . . .
H7A H 0.6018 -0.2657 0.5395 0.066 Uiso 1 1 calc R . .
C8 C 0.7190(3) -0.3976(2) 0.50722(17) 0.0680(8) Uani 1 1 d . . .
H8B H 0.6642 -0.4593 0.5206 0.082 Uiso 1 1 calc R . .
C9 C 0.8358(4) -0.4220(3) 0.47601(18) 0.0705(9) Uani 1 1 d . . .
H9A H 0.8594 -0.5002 0.4680 0.085 Uiso 1 1 calc R . .
C10 C 0.9175(3) -0.3321(3) 0.45667(17) 0.0676(8) Uani 1 1 d . . .
H10B H 0.9959 -0.3497 0.4349 0.081 Uiso 1 1 calc R . .
C11 C 0.8841(3) -0.2145(2) 0.46937(14) 0.0512(7) Uani 1 1 d . . .
H11A H 0.9409 -0.1523 0.4576 0.061 Uiso 1 1 calc R . .
C12 C 0.5003(2) 0.2506(2) 0.73942(13) 0.0377(6) Uani 1 1 d . . .
C13 C 0.3669(2) 0.2597(2) 0.72271(13) 0.0424(6) Uani 1 1 d . . .
H13A H 0.3165 0.2140 0.6708 0.051 Uiso 1 1 calc R . .
C14 C 0.3080(3) 0.3372(2) 0.78368(15) 0.0460(6) Uani 1 1 d . . .
H14A H 0.2182 0.3455 0.7734 0.055 Uiso 1 1 calc R . .
C15 C 0.3854(3) 0.4009(2) 0.85897(15) 0.0471(6) Uani 1 1 d . . .
C16 C 0.5174(3) 0.3943(2) 0.87700(15) 0.0540(7) Uani 1 1 d . . .
H16A H 0.5671 0.4403 0.9291 0.065 Uiso 1 1 calc R . .
C17 C 0.5764(3) 0.3176(2) 0.81588(14) 0.0477(6) Uani 1 1 d . . .
H17A H 0.6668 0.3114 0.8265 0.057 Uiso 1 1 calc R . .
C18 C 0.8298(3) 0.1411(3) 0.35174(16) 0.0708(9) Uani 1 1 d . . .
H18A H 0.8457 0.1942 0.3185 0.106 Uiso 1 1 calc R . .
H18B H 0.7771 0.0610 0.3175 0.106 Uiso 1 1 calc R . .
H18C H 0.9150 0.1295 0.3755 0.106 Uiso 1 1 calc R . .
C19 C 0.5374(3) -0.0831(2) 0.76215(15) 0.0558(7) Uani 1 1 d . . .
H19A H 0.4999 -0.0863 0.8110 0.084 Uiso 1 1 calc R . .
H19B H 0.6313 -0.0894 0.7691 0.084 Uiso 1 1 calc R . .
H19C H 0.4890 -0.1517 0.7147 0.084 Uiso 1 1 calc R . .
C20 C 0.1005(2) -0.0867(2) 1.15597(13) 0.0386(6) Uani 1 1 d . . .
C21 C 0.1516(2) -0.0950(2) 1.08069(13) 0.0358(5) Uani 1 1 d . . .
C22 C 0.2005(2) -0.1916(2) 1.02049(13) 0.0386(6) Uani 1 1 d . . .
C23 C 0.2458(2) -0.0255(2) 0.95726(13) 0.0388(6) Uani 1 1 d . . .
C24 C 0.1565(2) 0.0218(2) 1.07349(13) 0.0370(5) Uani 1 1 d . . .
C25 C 0.1141(2) 0.2272(2) 1.16913(14) 0.0384(5) Uani 1 1 d . . .
C26 C 0.0982(2) 0.2903(2) 1.11227(15) 0.0460(6) Uani 1 1 d . . .
H26A H 0.0837 0.2471 1.0553 0.055 Uiso 1 1 calc R . .
C27 C 0.1043(3) 0.4190(2) 1.14250(17) 0.0575(7) Uani 1 1 d . . .
H27A H 0.0939 0.4626 1.1053 0.069 Uiso 1 1 calc R . .
C28 C 0.1254(3) 0.4828(2) 1.22585(18) 0.0647(8) Uani 1 1 d . . .
H28A H 0.1296 0.5693 1.2451 0.078 Uiso 1 1 calc R . .
C29 C 0.1404(3) 0.4193(2) 1.28143(17) 0.0634(8) Uani 1 1 d . . .
H29A H 0.1543 0.4631 1.3383 0.076 Uiso 1 1 calc R . .
C30 C 0.1350(3) 0.2910(2) 1.25373(14) 0.0490(6) Uani 1 1 d . . .
H30A H 0.1452 0.2482 1.2914 0.059 Uiso 1 1 calc R . .
C31 C 0.3139(2) -0.2265(2) 0.89507(14) 0.0388(6) Uani 1 1 d . . .
C32 C 0.4488(3) -0.2300(2) 0.91309(16) 0.0498(6) Uani 1 1 d . . .
H32A H 0.4970 -0.1827 0.9654 0.060 Uiso 1 1 calc R . .
C33 C 0.5127(3) -0.3034(3) 0.85372(19) 0.0592(8) Uani 1 1 d . . .
H33A H 0.6040 -0.3060 0.8650 0.071 Uiso 1 1 calc R . .
C34 C 0.4384(3) -0.3714(2) 0.77854(19) 0.0582(8) Uani 1 1 d . . .
C35 C 0.3041(3) -0.3715(2) 0.75921(15) 0.0550(7) Uani 1 1 d . . .
H35A H 0.2565 -0.4198 0.7069 0.066 Uiso 1 1 calc R . .
C36 C 0.2403(3) -0.2984(2) 0.81867(14) 0.0455(6) Uani 1 1 d . . .
H36A H 0.1485 -0.2977 0.8073 0.055 Uiso 1 1 calc R . .
C37 C 0.0263(3) -0.1253(2) 1.29538(14) 0.0591(7) Uani 1 1 d . . .
H37A H 0.0077 -0.1822 1.3258 0.089 Uiso 1 1 calc R . .
H37B H -0.0533 -0.0918 1.2858 0.089 Uiso 1 1 calc R . .
H37C H 0.0993 -0.0578 1.3269 0.089 Uiso 1 1 calc R . .
C38 C 0.2848(3) 0.1135(2) 0.88120(14) 0.0538(7) Uani 1 1 d . . .
H38A H 0.3237 0.1179 0.8330 0.081 Uiso 1 1 calc R . .
H38B H 0.3324 0.1812 0.9293 0.081 Uiso 1 1 calc R . .
H38C H 0.1910 0.1201 0.8736 0.081 Uiso 1 1 calc R . .
N1 N 0.7653(2) -0.00791(17) 0.45549(10) 0.0421(5) Uani 1 1 d . . .
N2 N 0.73033(19) -0.07087(16) 0.50991(10) 0.0400(5) Uani 1 1 d . . .
N3 N 0.55992(19) 0.16631(17) 0.67673(11) 0.0393(5) Uani 1 1 d . . .
N4 N 0.62654(19) -0.03388(17) 0.63447(11) 0.0406(5) Uani 1 1 d . . .
N5 N 0.6067(2) 0.31419(19) 0.60445(12) 0.0505(6) Uani 1 1 d . . .
H5A H 0.573(3) 0.359(2) 0.6422(15) 0.061 Uiso 1 1 d . . .
N6 N 0.07581(19) 0.02716(17) 1.19300(11) 0.0418(5) Uani 1 1 d . . .
N7 N 0.10983(19) 0.09462(17) 1.14073(11) 0.0388(5) Uani 1 1 d . . .
N8 N 0.20100(19) 0.06072(17) 1.01101(11) 0.0399(5) Uani 1 1 d . . .
N9 N 0.25064(19) -0.14551(17) 0.95764(10) 0.0388(5) Uani 1 1 d . . .
N10 N 0.1993(2) -0.30118(19) 1.02346(12) 0.0508(6) Uani 1 1 d . . .
H10A H 0.229(3) -0.346(2) 0.9817(15) 0.061 Uiso 1 1 d . . .


_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
S1 C1 1.745(2) . ?
S1 C18 1.794(2) . ?
S2 C20 1.740(2) . ?
S2 C37 1.787(2) . ?
O1 C4 1.336(2) . ?
O1 C19 1.445(2) . ?
O2 C23 1.329(2) . ?
O2 C38 1.441(2) . ?
F1 C15 1.363(2) . ?
F2 C34 1.355(3) . ?
C1 N1 1.325(3) . ?
C1 C2 1.413(3) . ?
C2 C5 1.376(3) . ?
C2 C3 1.440(3) . ?
C3 N5 1.265(3) . ?
C3 N3 1.435(2) . ?
C4 N4 1.289(3) . ?
C4 N3 1.373(3) . ?
C5 N4 1.359(2) . ?
C5 N2 1.359(2) . ?
C6 C11 1.379(3) . ?
C6 C7 1.382(3) . ?
C6 N2 1.428(3) . ?
C7 C8 1.385(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.371(4) . ?
C8 H8B 0.9300 . ?
C9 C10 1.362(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.388(3) . ?
C10 H10B 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.375(3) . ?
C12 C17 1.375(3) . ?
C12 N3 1.445(2) . ?
C13 C14 1.388(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.360(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.357(3) . ?
C16 C17 1.385(3) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N6 1.327(3) . ?
C20 C21 1.416(3) . ?
C21 C24 1.370(3) . ?
C21 C22 1.438(3) . ?
C22 N10 1.265(3) . ?
C22 N9 1.440(3) . ?
C23 N8 1.290(3) . ?
C23 N9 1.379(3) . ?
C24 N7 1.363(2) . ?
C24 N8 1.369(2) . ?
C25 C30 1.381(3) . ?
C25 C26 1.390(3) . ?
C25 N7 1.429(3) . ?
C26 C27 1.384(3) . ?
C26 H26A 0.9300 . ?
C27 C28 1.363(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.375(3) . ?
C28 H28A 0.9300 . ?
C29 C30 1.380(3) . ?
C29 H29A 0.9300 . ?
C30 H30A 0.9300 . ?
C31 C36 1.376(3) . ?
C31 C32 1.376(3) . ?
C31 N9 1.448(3) . ?
C32 C33 1.380(3) . ?
C32 H32A 0.9300 . ?
C33 C34 1.355(4) . ?
C33 H33A 0.9300 . ?
C34 C35 1.364(4) . ?
C35 C36 1.378(3) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
N1 N2 1.384(2) . ?
N5 H5A 0.83(2) . ?
N6 N7 1.387(2) . ?
N10 H10A 0.85(2) . ?

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
C1 S1 C18 100.37(11) . . ?
C20 S2 C37 100.55(11) . . ?
C4 O1 C19 115.82(18) . . ?
C23 O2 C38 116.86(17) . . ?
N1 C1 C2 111.52(18) . . ?
N1 C1 S1 123.31(16) . . ?
C2 C1 S1 125.15(17) . . ?
C5 C2 C1 105.02(18) . . ?
C5 C2 C3 120.09(18) . . ?
C1 C2 C3 134.8(2) . . ?
N5 C3 N3 125.8(2) . . ?
N5 C3 C2 123.4(2) . . ?
N3 C3 C2 110.76(18) . . ?
N4 C4 O1 120.6(2) . . ?
N4 C4 N3 127.58(19) . . ?
O1 C4 N3 111.83(19) . . ?
N4 C5 N2 125.2(2) . . ?
N4 C5 C2 127.3(2) . . ?
N2 C5 C2 107.50(18) . . ?
C11 C6 C7 120.9(2) . . ?
C11 C6 N2 118.5(2) . . ?
C7 C6 N2 120.5(2) . . ?
C6 C7 C8 118.6(3) . . ?
C6 C7 H7A 120.7 . . ?
C8 C7 H7A 120.7 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8B 119.7 . . ?
C7 C8 H8B 119.7 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10B 119.9 . . ?
C11 C10 H10B 119.9 . . ?
C6 C11 C10 119.2(3) . . ?
C6 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 . . ?
C13 C12 C17 120.9(2) . . ?
C13 C12 N3 119.5(2) . . ?
C17 C12 N3 119.6(2) . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
C15 C14 C13 118.0(2) . . ?
C15 C14 H14A 121.0 . . ?
C13 C14 H14A 121.0 . . ?
C16 C15 C14 123.6(2) . . ?
C16 C15 F1 118.6(2) . . ?
C14 C15 F1 117.8(2) . . ?
C15 C16 C17 118.4(2) . . ?
C15 C16 H16A 120.8 . . ?
C17 C16 H16A 120.8 . . ?
C12 C17 C16 119.5(2) . . ?
C12 C17 H17A 120.3 . . ?
C16 C17 H17A 120.3 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N6 C20 C21 111.60(19) . . ?
N6 C20 S2 122.62(16) . . ?
C21 C20 S2 125.78(17) . . ?
C24 C21 C20 105.03(19) . . ?
C24 C21 C22 120.76(18) . . ?
C20 C21 C22 134.1(2) . . ?
N10 C22 C21 124.1(2) . . ?
N10 C22 N9 125.4(2) . . ?
C21 C22 N9 110.49(19) . . ?
N8 C23 O2 121.3(2) . . ?
N8 C23 N9 127.09(19) . . ?
O2 C23 N9 111.62(18) . . ?
N7 C24 N8 125.4(2) . . ?
N7 C24 C21 107.72(18) . . ?
N8 C24 C21 126.9(2) . . ?
C30 C25 C26 121.0(2) . . ?
C30 C25 N7 118.7(2) . . ?
C26 C25 N7 120.3(2) . . ?
C27 C26 C25 118.4(2) . . ?
C27 C26 H26A 120.8 . . ?
C25 C26 H26A 120.8 . . ?
C28 C27 C26 121.1(2) . . ?
C28 C27 H27A 119.4 . . ?
C26 C27 H27A 119.4 . . ?
C27 C28 C29 119.9(2) . . ?
C27 C28 H28A 120.0 . . ?
C29 C28 H28A 120.0 . . ?
C28 C29 C30 120.7(2) . . ?
C28 C29 H29A 119.7 . . ?
C30 C29 H29A 119.7 . . ?
C29 C30 C25 118.9(2) . . ?
C29 C30 H30A 120.5 . . ?
C25 C30 H30A 120.5 . . ?
C36 C31 C32 120.6(2) . . ?
C36 C31 N9 120.5(2) . . ?
C32 C31 N9 118.9(2) . . ?
C31 C32 C33 120.1(3) . . ?
C31 C32 H32A 119.9 . . ?
C33 C32 H32A 119.9 . . ?
C34 C33 C32 118.0(3) . . ?
C34 C33 H33A 121.0 . . ?
C32 C33 H33A 121.0 . . ?
F2 C34 C33 118.7(3) . . ?
F2 C34 C35 118.1(3) . . ?
C33 C34 C35 123.2(2) . . ?
C34 C35 C36 118.7(3) . . ?
C34 C35 H35A 120.6 . . ?
C36 C35 H35A 120.6 . . ?
C31 C36 C35 119.3(2) . . ?
C31 C36 H36A 120.3 . . ?
C35 C36 H36A 120.3 . . ?
S2 C37 H37A 109.5 . . ?
S2 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
S2 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O2 C38 H38A 109.5 . . ?
O2 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O2 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C1 N1 N2 105.18(16) . . ?
C5 N2 N1 110.78(17) . . ?
C5 N2 C6 129.31(18) . . ?
N1 N2 C6 119.85(17) . . ?
C4 N3 C3 122.03(18) . . ?
C4 N3 C12 118.99(17) . . ?
C3 N3 C12 118.91(17) . . ?
C4 N4 C5 112.13(18) . . ?
C3 N5 H5A 111.5(17) . . ?
C20 N6 N7 105.02(16) . . ?
C24 N7 N6 110.63(17) . . ?
C24 N7 C25 129.55(18) . . ?
N6 N7 C25 118.84(17) . . ?
C23 N8 C24 112.39(19) . . ?
C23 N9 C22 122.29(18) . . ?
C23 N9 C31 119.15(17) . . ?
C22 N9 C31 118.50(17) . . ?
C22 N10 H10A 110.5(16) . . ?

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
C18 S1 C1 N1 -3.7(2) . . . . ?
C18 S1 C1 C2 178.1(2) . . . . ?
N1 C1 C2 C5 -0.3(3) . . . . ?
S1 C1 C2 C5 178.14(17) . . . . ?
N1 C1 C2 C3 175.5(2) . . . . ?
S1 C1 C2 C3 -6.1(4) . . . . ?
C5 C2 C3 N5 175.8(2) . . . . ?
C1 C2 C3 N5 0.5(4) . . . . ?
C5 C2 C3 N3 -3.5(3) . . . . ?
C1 C2 C3 N3 -178.8(2) . . . . ?
C19 O1 C4 N4 0.8(3) . . . . ?
C19 O1 C4 N3 -179.1(2) . . . . ?
C1 C2 C5 N4 177.6(2) . . . . ?
C3 C2 C5 N4 1.1(4) . . . . ?
C1 C2 C5 N2 0.1(2) . . . . ?
C3 C2 C5 N2 -176.5(2) . . . . ?
C11 C6 C7 C8 0.0(4) . . . . ?
N2 C6 C7 C8 179.2(2) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C7 C6 C11 C10 1.2(4) . . . . ?
N2 C6 C11 C10 -178.0(2) . . . . ?
C9 C10 C11 C6 -1.7(4) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
N3 C12 C13 C14 177.81(19) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
C13 C14 C15 F1 -178.0(2) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
F1 C15 C16 C17 178.4(2) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
N3 C12 C17 C16 -177.3(2) . . . . ?
C15 C16 C17 C12 -0.1(4) . . . . ?
C37 S2 C20 N6 -5.1(2) . . . . ?
C37 S2 C20 C21 174.3(2) . . . . ?
N6 C20 C21 C24 -0.2(3) . . . . ?
S2 C20 C21 C24 -179.71(18) . . . . ?
N6 C20 C21 C22 176.0(2) . . . . ?
S2 C20 C21 C22 -3.5(4) . . . . ?
C24 C21 C22 N10 179.8(2) . . . . ?
C20 C21 C22 N10 4.1(4) . . . . ?
C24 C21 C22 N9 0.1(3) . . . . ?
C20 C21 C22 N9 -175.6(2) . . . . ?
C38 O2 C23 N8 -6.0(3) . . . . ?
C38 O2 C23 N9 174.50(19) . . . . ?
C20 C21 C24 N7 -0.4(3) . . . . ?
C22 C21 C24 N7 -177.2(2) . . . . ?
C20 C21 C24 N8 179.1(2) . . . . ?
C22 C21 C24 N8 2.2(4) . . . . ?
C30 C25 C26 C27 0.3(4) . . . . ?
N7 C25 C26 C27 -179.4(2) . . . . ?
C25 C26 C27 C28 0.0(4) . . . . ?
C26 C27 C28 C29 -0.3(4) . . . . ?
C27 C28 C29 C30 0.3(4) . . . . ?
C28 C29 C30 C25 0.0(4) . . . . ?
C26 C25 C30 C29 -0.3(4) . . . . ?
N7 C25 C30 C29 179.4(2) . . . . ?
C36 C31 C32 C33 1.7(3) . . . . ?
N9 C31 C32 C33 -178.00(19) . . . . ?
C31 C32 C33 C34 -0.5(4) . . . . ?
C32 C33 C34 F2 178.5(2) . . . . ?
C32 C33 C34 C35 -0.5(4) . . . . ?
F2 C34 C35 C36 -178.7(2) . . . . ?
C33 C34 C35 C36 0.3(4) . . . . ?
C32 C31 C36 C35 -1.9(3) . . . . ?
N9 C31 C36 C35 177.8(2) . . . . ?
C34 C35 C36 C31 0.9(3) . . . . ?
C2 C1 N1 N2 0.4(3) . . . . ?
S1 C1 N1 N2 -178.09(16) . . . . ?
N4 C5 N2 N1 -177.5(2) . . . . ?
C2 C5 N2 N1 0.2(3) . . . . ?
N4 C5 N2 C6 -0.3(4) . . . . ?
C2 C5 N2 C6 177.3(2) . . . . ?
C1 N1 N2 C5 -0.3(2) . . . . ?
C1 N1 N2 C6 -177.8(2) . . . . ?
C11 C6 N2 C5 -143.9(2) . . . . ?
C7 C6 N2 C5 36.8(4) . . . . ?
C11 C6 N2 N1 33.0(3) . . . . ?
C7 C6 N2 N1 -146.2(2) . . . . ?
N4 C4 N3 C3 -1.7(4) . . . . ?
O1 C4 N3 C3 178.23(19) . . . . ?
N4 C4 N3 C12 -178.6(2) . . . . ?
O1 C4 N3 C12 1.2(3) . . . . ?
N5 C3 N3 C4 -175.5(2) . . . . ?
C2 C3 N3 C4 3.8(3) . . . . ?
N5 C3 N3 C12 1.5(4) . . . . ?
C2 C3 N3 C12 -179.2(2) . . . . ?
C13 C12 N3 C4 -100.9(3) . . . . ?
C17 C12 N3 C4 77.0(3) . . . . ?
C13 C12 N3 C3 82.0(3) . . . . ?
C17 C12 N3 C3 -100.1(2) . . . . ?
O1 C4 N4 C5 179.0(2) . . . . ?
N3 C4 N4 C5 -1.1(4) . . . . ?
N2 C5 N4 C4 178.5(2) . . . . ?
C2 C5 N4 C4 1.4(3) . . . . ?
C21 C20 N6 N7 0.7(3) . . . . ?
S2 C20 N6 N7 -179.81(16) . . . . ?
N8 C24 N7 N6 -178.6(2) . . . . ?
C21 C24 N7 N6 0.8(3) . . . . ?
N8 C24 N7 C25 -10.3(4) . . . . ?
C21 C24 N7 C25 169.1(2) . . . . ?
C20 N6 N7 C24 -0.9(2) . . . . ?
C20 N6 N7 C25 -170.7(2) . . . . ?
C30 C25 N7 C24 -143.6(2) . . . . ?
C26 C25 N7 C24 36.1(4) . . . . ?
C30 C25 N7 N6 23.9(3) . . . . ?
C26 C25 N7 N6 -156.4(2) . . . . ?
O2 C23 N8 C24 -178.8(2) . . . . ?
N9 C23 N8 C24 0.6(3) . . . . ?
N7 C24 N8 C23 176.8(2) . . . . ?
C21 C24 N8 C23 -2.5(3) . . . . ?
N8 C23 N9 C22 1.6(4) . . . . ?
O2 C23 N9 C22 -178.93(19) . . . . ?
N8 C23 N9 C31 -175.5(2) . . . . ?
O2 C23 N9 C31 4.0(3) . . . . ?
N10 C22 N9 C23 178.4(2) . . . . ?
C21 C22 N9 C23 -1.8(3) . . . . ?
N10 C22 N9 C31 -4.4(4) . . . . ?
C21 C22 N9 C31 175.3(2) . . . . ?
C36 C31 N9 C23 -86.5(3) . . . . ?
C32 C31 N9 C23 93.2(3) . . . . ?
C36 C31 N9 C22 96.3(2) . . . . ?
C32 C31 N9 C22 -84.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        28.23
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_WJJ3
_database_code_depnum_ccdc_archive 'CCDC 850785'
_audit_update_record             
;
2011-10-26 deposited with the CCDC.
2015-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 F N5 O S'
_chemical_formula_sum            'C20 H18 F N5 O S'
_chemical_formula_weight         395.45

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc

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

_cell_length_a                   20.583(3)
_cell_length_b                   15.434(3)
_cell_length_c                   13.875(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.671(2)
_cell_angle_gamma                90.00
_cell_volume                     3751.4(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3260
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      24.27

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9340
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   '(SADABS; Bruker 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16452
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_sigmaI/netI    0.0844
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         28.02
_reflns_number_total             4519
_reflns_number_gt                2007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0582P)²+2.8894P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4519
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1714
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1633
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_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
O1 O 0.32024(11) 0.08631(13) 0.20715(18) 0.0588(6) Uani 1 1 d . . .
S1 S 0.68447(5) 0.22267(6) 0.54364(9) 0.0746(3) Uani 1 1 d . . .
F1 F 0.35088(12) 0.59925(13) 0.2083(2) 0.1010(8) Uani 1 1 d . . .
C1 C 0.61844(16) 0.1377(2) 0.4862(3) 0.0544(8) Uani 1 1 d . . .
C2 C 0.53854(16) 0.14290(19) 0.4114(3) 0.0488(8) Uani 1 1 d . . .
C3 C 0.48278(16) 0.20815(19) 0.3576(3) 0.0475(7) Uani 1 1 d . . .
C4 C 0.39473(17) 0.1007(2) 0.2765(3) 0.0497(8) Uani 1 1 d . . .
C5 C 0.51364(16) 0.05906(19) 0.3888(3) 0.0460(7) Uani 1 1 d . . .
C6 C 0.46044(16) 0.36793(19) 0.3311(3) 0.0508(8) Uani 1 1 d . . .
C7 C 0.49752(18) 0.4455(2) 0.3764(3) 0.0634(9) Uani 1 1 d . . .
H7A H 0.5482 0.4450 0.4357 0.076 Uiso 1 1 calc R . .
C8 C 0.4610(2) 0.5231(2) 0.3357(3) 0.0746(11) Uani 1 1 d . . .
H8A H 0.4863 0.5752 0.3665 0.090 Uiso 1 1 calc R . .
C9 C 0.3871(2) 0.5221(2) 0.2492(3) 0.0676(10) Uani 1 1 d . . .
C10 C 0.34850(19) 0.4480(2) 0.2031(3) 0.0637(9) Uani 1 1 d . . .
H10A H 0.2976 0.4495 0.1446 0.076 Uiso 1 1 calc R . .
C11 C 0.38526(17) 0.3701(2) 0.2433(3) 0.0583(9) Uani 1 1 d . . .
H11A H 0.3593 0.3187 0.2113 0.070 Uiso 1 1 calc R . .
C12 C 0.58257(18) -0.0845(2) 0.4510(3) 0.0525(8) Uani 1 1 d . . .
C13 C 0.5197(2) -0.1366(2) 0.3923(3) 0.0731(10) Uani 1 1 d . . .
H13A H 0.4712 -0.1123 0.3509 0.088 Uiso 1 1 calc R . .
C14 C 0.5286(2) -0.2248(2) 0.3951(4) 0.0916(13) Uani 1 1 d . . .
H14A H 0.4858 -0.2599 0.3549 0.110 Uiso 1 1 calc R . .
C15 C 0.5987(3) -0.2621(3) 0.4551(4) 0.0865(12) Uani 1 1 d . . .
H15A H 0.6040 -0.3220 0.4561 0.104 Uiso 1 1 calc R . .
C16 C 0.6616(2) -0.2100(3) 0.5142(4) 0.0854(12) Uani 1 1 d . . .
H16A H 0.7098 -0.2349 0.5556 0.102 Uiso 1 1 calc R . .
C17 C 0.6540(2) -0.1214(2) 0.5131(3) 0.0720(10) Uani 1 1 d . . .
H17A H 0.6969 -0.0865 0.5541 0.086 Uiso 1 1 calc R . .
C18 C 0.6982(2) 0.2342(3) 0.6792(3) 0.0998(14) Uani 1 1 d . . .
H18A H 0.7342 0.2799 0.7191 0.150 Uiso 1 1 calc R . .
H18B H 0.7174 0.1810 0.7203 0.150 Uiso 1 1 calc R . .
H18C H 0.6504 0.2482 0.6722 0.150 Uiso 1 1 calc R . .
C19 C 0.29534(18) -0.0017(2) 0.1877(3) 0.0650(9) Uani 1 1 d . . .
H19A H 0.3033 -0.0275 0.2569 0.078 Uiso 1 1 calc R . .
H19B H 0.3238 -0.0349 0.1626 0.078 Uiso 1 1 calc R . .
C20 C 0.2126(2) -0.0013(3) 0.0988(3) 0.0862(12) Uani 1 1 d . . .
H20A H 0.1937 -0.0597 0.0838 0.129 Uiso 1 1 calc R . .
H20B H 0.2056 0.0239 0.0307 0.129 Uiso 1 1 calc R . .
H20C H 0.1852 0.0321 0.1244 0.129 Uiso 1 1 calc R . .
N1 N 0.57581(13) 0.00689(16) 0.4480(2) 0.0513(7) Uani 1 1 d . . .
N2 N 0.64074(14) 0.05647(18) 0.5081(2) 0.0578(7) Uani 1 1 d . . .
N3 N 0.41001(13) 0.18604(16) 0.2894(2) 0.0507(7) Uani 1 1 d . . .
N4 N 0.44043(13) 0.03384(15) 0.3205(2) 0.0494(6) Uani 1 1 d . . .
N5 N 0.50345(13) 0.29266(16) 0.3749(2) 0.0576(7) Uani 1 1 d . . .
H5A H 0.5515 0.3013 0.4209 0.069 Uiso 1 1 calc R . .


_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
O1 C4 1.333(3) . ?
O1 C19 1.426(4) . ?
S1 C1 1.751(3) . ?
S1 C18 1.758(4) . ?
F1 C9 1.361(4) . ?
C1 N2 1.315(4) . ?
C1 C2 1.413(4) . ?
C2 C5 1.366(4) . ?
C2 C3 1.410(4) . ?
C3 N3 1.329(3) . ?
C3 N5 1.354(4) . ?
C4 N4 1.311(4) . ?
C4 N3 1.344(4) . ?
C5 N4 1.349(4) . ?
C5 N1 1.363(4) . ?
C6 C11 1.378(4) . ?
C6 C7 1.381(4) . ?
C6 N5 1.392(4) . ?
C7 C8 1.368(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.357(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.347(5) . ?
C10 C11 1.372(4) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.370(4) . ?
C12 C17 1.378(4) . ?
C12 N1 1.416(4) . ?
C13 C14 1.373(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.358(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.370(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.376(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.488(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 N2 1.377(3) . ?
N5 H5A 0.8600 . ?

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
C4 O1 C19 117.3(2) . . ?
C1 S1 C18 102.31(17) . . ?
N2 C1 C2 110.8(3) . . ?
N2 C1 S1 121.0(2) . . ?
C2 C1 S1 128.2(2) . . ?
C5 C2 C3 116.9(3) . . ?
C5 C2 C1 105.5(3) . . ?
C3 C2 C1 137.7(3) . . ?
N3 C3 N5 120.4(3) . . ?
N3 C3 C2 119.5(3) . . ?
N5 C3 C2 120.1(3) . . ?
N4 C4 O1 118.5(3) . . ?
N4 C4 N3 130.4(3) . . ?
O1 C4 N3 111.1(3) . . ?
N4 C5 N1 127.0(3) . . ?
N4 C5 C2 125.5(3) . . ?
N1 C5 C2 107.5(3) . . ?
C11 C6 C7 118.4(3) . . ?
C11 C6 N5 124.6(3) . . ?
C7 C6 N5 116.9(3) . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7A 119.4 . . ?
C6 C7 H7A 119.4 . . ?
C9 C8 C7 118.2(3) . . ?
C9 C8 H8A 120.9 . . ?
C7 C8 H8A 120.9 . . ?
C10 C9 C8 122.5(3) . . ?
C10 C9 F1 119.2(3) . . ?
C8 C9 F1 118.2(3) . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
C10 C11 C6 120.3(3) . . ?
C10 C11 H11A 119.8 . . ?
C6 C11 H11A 119.8 . . ?
C13 C12 C17 119.6(3) . . ?
C13 C12 N1 121.3(3) . . ?
C17 C12 N1 119.1(3) . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C15 C14 C13 121.4(4) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
C14 C15 C16 118.9(4) . . ?
C14 C15 H15A 120.5 . . ?
C16 C15 H15A 120.5 . . ?
C15 C16 C17 120.7(4) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.6 . . ?
C16 C17 C12 119.7(4) . . ?
C16 C17 H17A 120.2 . . ?
C12 C17 H17A 120.2 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C20 107.1(3) . . ?
O1 C19 H19A 110.3 . . ?
C20 C19 H19A 110.3 . . ?
O1 C19 H19B 110.3 . . ?
C20 C19 H19B 110.3 . . ?
H19A C19 H19B 108.5 . . ?
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 . . ?
C5 N1 N2 110.0(2) . . ?
C5 N1 C12 130.8(3) . . ?
N2 N1 C12 119.1(2) . . ?
C1 N2 N1 106.3(2) . . ?
C3 N3 C4 116.3(2) . . ?
C4 N4 C5 111.3(3) . . ?
C3 N5 C6 131.2(2) . . ?
C3 N5 H5A 114.4 . . ?
C6 N5 H5A 114.4 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.045


