# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1825053'
_audit_update_record             
;
2018-02-21 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_shelx               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.959 Why?  
RESPONSE: The sample was not of good quality and did not diffract particularly
well. The structure has been determined unambiguously and is in entirely  
accord with spectroscopy recorded on the bulk sample.
;
_vrf_PLAT084_shelx               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.38 Report
RESPONSE: The sample was not of good quality and did not diffract particularly
well.
;
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01318 Ang.  
RESPONSE: The sample was not of good quality and did not diffract particularly
well.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F N4 S'
_chemical_formula_sum            'C13 H9 F N4 S'
_chemical_formula_weight         272.30

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.8207(16)
_cell_length_b                   17.650(3)
_cell_length_c                   13.3819(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.691(5)
_cell_angle_gamma                90
_cell_volume                     2519.3(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8731
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      24.95

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43705
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_av_R_equivalents  0.1311
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.308
_diffrn_reflns_theta_max         25.713
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             4590
_reflns_number_gt                2246
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 1996)'
_computing_cell_refinement       'SAINT (Bruker, 1996)'
_computing_data_reduction        'SAINT (Bruker, 1996)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1555P)²+12.5760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4590
_refine_ls_number_parameters     349
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2037
_refine_ls_R_factor_gt           0.1102
_refine_ls_wR_factor_ref         0.3847
_refine_ls_wR_factor_gt          0.3049
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.025
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.0224(2) -0.13419(12) 0.58447(16) 0.0637(7) Uani 1 1 d . . . . .
F1 F 0.9342(7) -0.0950(4) 1.0697(4) 0.116(2) Uani 1 1 d . . . . .
N1 N 0.8519(7) -0.0435(4) 0.6584(5) 0.0637(19) Uani 1 1 d D . . . .
H1N H 0.790(6) -0.011(4) 0.642(6) 0.076 Uiso 1 1 d D U . . .
N2 N 0.8559(7) -0.0456(4) 0.4873(5) 0.0595(18) Uani 1 1 d . . . . .
N3 N 0.9186(7) -0.0781(4) 0.4172(4) 0.0584(18) Uani 1 1 d . . . . .
N4 N 1.1690(7) -0.2117(4) 0.4485(6) 0.072(2) Uani 1 1 d . . . . .
C1 C 0.9008(8) -0.0695(4) 0.5794(5) 0.054(2) Uani 1 1 d . . . . .
C2 C 1.0063(8) -0.1252(4) 0.4553(6) 0.053(2) Uani 1 1 d . . . . .
C3 C 1.0840(8) -0.1644(4) 0.3949(6) 0.054(2) Uani 1 1 d . . . . .
C4 C 1.2457(9) -0.2486(5) 0.3967(8) 0.076(3) Uani 1 1 d . . . . .
H4 H 1.3073 -0.2793 0.4330 0.092 Uiso 1 1 calc R U . . .
C5 C 1.2396(11) -0.2440(6) 0.2928(9) 0.087(3) Uani 1 1 d . . . . .
H5 H 1.2925 -0.2726 0.2596 0.105 Uiso 1 1 calc R U . . .
C6 C 1.1516(11) -0.1950(6) 0.2397(7) 0.080(3) Uani 1 1 d . . . . .
H6 H 1.1464 -0.1890 0.1701 0.096 Uiso 1 1 calc R U . . .
C7 C 1.0717(9) -0.1552(5) 0.2912(7) 0.069(2) Uani 1 1 d . . . . .
H7 H 1.0111 -0.1229 0.2568 0.083 Uiso 1 1 calc R U . . .
C8 C 0.8798(8) -0.0569(4) 0.7612(5) 0.053(2) Uani 1 1 d . . . . .
C9 C 0.9853(8) -0.0941(5) 0.8104(6) 0.060(2) Uani 1 1 d . . . . .
H9 H 1.0449 -0.1120 0.7736 0.072 Uiso 1 1 calc R U . . .
C10 C 1.0023(10) -0.1050(5) 0.9147(6) 0.071(3) Uani 1 1 d . . . . .
H10 H 1.0749 -0.1284 0.9476 0.085 Uiso 1 1 calc R U . . .
C11 C 0.9167(10) -0.0825(5) 0.9673(6) 0.072(3) Uani 1 1 d . . . . .
C12 C 0.8139(10) -0.0449(6) 0.9229(6) 0.079(3) Uani 1 1 d . . . . .
H12 H 0.7563 -0.0274 0.9619 0.094 Uiso 1 1 calc R U . . .
C13 C 0.7936(9) -0.0322(5) 0.8203(6) 0.071(3) Uani 1 1 d . . . . .
H13 H 0.7215 -0.0070 0.7899 0.086 Uiso 1 1 calc R U . . .
S1A S 0.4631(2) 0.13888(12) 0.49792(16) 0.0644(7) Uani 1 1 d . . . . .
F1A F 0.5500(7) 0.0891(3) 0.0109(4) 0.103(2) Uani 1 1 d . . . . .
N1A N 0.6451(7) 0.0554(4) 0.4254(5) 0.0574(17) Uani 1 1 d D . . . .
H1AN H 0.713(5) 0.028(4) 0.443(6) 0.069 Uiso 1 1 d D U . . .
N2A N 0.6368(7) 0.0553(4) 0.5960(5) 0.0607(18) Uani 1 1 d . . . . .
N3A N 0.5722(7) 0.0845(4) 0.6655(5) 0.0596(18) Uani 1 1 d . . . . .
N4A N 0.3093(7) 0.2109(4) 0.6340(6) 0.067(2) Uani 1 1 d . . . . .
C1A C 0.5903(8) 0.0785(4) 0.5023(7) 0.062(2) Uani 1 1 d . . . . .
C2A C 0.4807(8) 0.1294(4) 0.6266(6) 0.0524(19) Uani 1 1 d . . . . .
C3A C 0.3961(9) 0.1673(4) 0.6853(6) 0.059(2) Uani 1 1 d . . . . .
C4A C 0.2301(10) 0.2455(5) 0.6860(8) 0.080(3) Uani 1 1 d . . . . .
H4A H 0.1669 0.2754 0.6502 0.096 Uiso 1 1 calc R U . . .
C5A C 0.2366(11) 0.2396(5) 0.7891(9) 0.089(3) Uani 1 1 d . . . . .
H5A H 0.1803 0.2653 0.8223 0.106 Uiso 1 1 calc R U . . .
C6A C 0.3275(11) 0.1952(6) 0.8409(8) 0.088(3) Uani 1 1 d . . . . .
H6A H 0.3331 0.1898 0.9107 0.106 Uiso 1 1 calc R U . . .
C7A C 0.4109(9) 0.1582(5) 0.7926(6) 0.065(2) Uani 1 1 d . . . . .
H7A H 0.4746 0.1284 0.8279 0.078 Uiso 1 1 calc R U . . .
C8A C 0.6151(8) 0.0678(4) 0.3196(6) 0.0519(19) Uani 1 1 d . . . . .
C9A C 0.5197(9) 0.1120(5) 0.2725(6) 0.070(2) Uani 1 1 d . . . . .
H9A H 0.4688 0.1374 0.3108 0.083 Uiso 1 1 calc R U . . .
C10A C 0.4978(10) 0.1194(6) 0.1677(7) 0.079(3) Uani 1 1 d . . . . .
H10A H 0.4329 0.1498 0.1353 0.095 Uiso 1 1 calc R U . . .
C11A C 0.5731(10) 0.0815(5) 0.1139(6) 0.068(2) Uani 1 1 d . . . . .
C12A C 0.6691(10) 0.0369(5) 0.1577(6) 0.074(3) Uani 1 1 d . . . . .
H12A H 0.7193 0.0112 0.1189 0.088 Uiso 1 1 calc R U . . .
C13A C 0.6899(9) 0.0308(5) 0.2632(6) 0.063(2) Uani 1 1 d . . . . .
H13A H 0.7556 0.0010 0.2955 0.076 Uiso 1 1 calc R U . . .


_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 C2 1.715(8) . ?
S1 C1 1.735(9) . ?
F1 C11 1.369(9) . ?
N1 C1 1.340(10) . ?
N1 C8 1.378(10) . ?
N1 H1N 0.882(10) . ?
N2 C1 1.316(9) . ?
N2 N3 1.372(9) . ?
N3 C2 1.300(10) . ?
N4 C4 1.336(11) . ?
N4 C3 1.354(10) . ?
C2 C3 1.439(11) . ?
C3 C7 1.380(11) . ?
C4 C5 1.384(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(12) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.384(11) . ?
C8 C13 1.390(11) . ?
C9 C10 1.390(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.316(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.345(13) . ?
C12 C13 1.373(11) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
S1A C2A 1.708(7) . ?
S1A C1A 1.733(9) . ?
F1A C11A 1.365(9) . ?
N1A C1A 1.336(10) . ?
N1A C8A 1.416(10) . ?
N1A H1AN 0.880(10) . ?
N2A C1A 1.334(10) . ?
N2A N3A 1.355(9) . ?
N3A C2A 1.306(10) . ?
N4A C3A 1.316(10) . ?
N4A C4A 1.339(11) . ?
C2A C3A 1.464(11) . ?
C3A C7A 1.427(11) . ?
C4A C5A 1.374(14) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.354(15) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.362(13) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C8A C9A 1.360(11) . ?
C8A C13A 1.362(11) . ?
C9A C10A 1.388(12) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.352(13) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.355(13) . ?
C12A C13A 1.396(11) . ?
C12A H12A 0.9300 . ?
C13A H13A 0.9300 . ?

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
C2 S1 C1 87.3(4) . . ?
C1 N1 C8 132.8(7) . . ?
C1 N1 H1N 115(6) . . ?
C8 N1 H1N 113(6) . . ?
C1 N2 N3 111.0(7) . . ?
C2 N3 N2 114.3(6) . . ?
C4 N4 C3 116.8(8) . . ?
N2 C1 N1 119.8(8) . . ?
N2 C1 S1 113.9(6) . . ?
N1 C1 S1 126.3(6) . . ?
N3 C2 C3 123.0(7) . . ?
N3 C2 S1 113.4(6) . . ?
C3 C2 S1 123.6(6) . . ?
N4 C3 C7 123.2(8) . . ?
N4 C3 C2 114.0(7) . . ?
C7 C3 C2 122.8(8) . . ?
N4 C4 C5 124.3(9) . . ?
N4 C4 H4 117.8 . . ?
C5 C4 H4 117.8 . . ?
C4 C5 C6 117.6(9) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C7 C6 C5 119.5(9) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C3 118.5(9) . . ?
C6 C7 H7 120.8 . . ?
C3 C7 H7 120.8 . . ?
N1 C8 C9 125.5(7) . . ?
N1 C8 C13 117.3(8) . . ?
C9 C8 C13 117.2(7) . . ?
C10 C9 C8 120.2(8) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.6(9) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 121.1(8) . . ?
C10 C11 F1 119.7(9) . . ?
C12 C11 F1 119.1(9) . . ?
C11 C12 C13 120.2(9) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.6(9) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C2A S1A C1A 87.3(4) . . ?
C1A N1A C8A 131.8(7) . . ?
C1A N1A H1AN 115(5) . . ?
C8A N1A H1AN 113(5) . . ?
C1A N2A N3A 111.8(7) . . ?
C2A N3A N2A 113.6(6) . . ?
C3A N4A C4A 117.3(8) . . ?
N1A C1A N2A 118.9(8) . . ?
N1A C1A S1A 128.0(7) . . ?
N2A C1A S1A 113.1(7) . . ?
N3A C2A C3A 124.3(7) . . ?
N3A C2A S1A 114.2(6) . . ?
C3A C2A S1A 121.4(6) . . ?
N4A C3A C7A 122.7(8) . . ?
N4A C3A C2A 116.3(7) . . ?
C7A C3A C2A 120.9(8) . . ?
N4A C4A C5A 124.0(9) . . ?
N4A C4A H4A 118.0 . . ?
C5A C4A H4A 118.0 . . ?
C6A C5A C4A 117.9(9) . . ?
C6A C5A H5A 121.1 . . ?
C4A C5A H5A 121.1 . . ?
C7A C6A C5A 121.2(10) . . ?
C7A C6A H6A 119.4 . . ?
C5A C6A H6A 119.4 . . ?
C6A C7A C3A 116.9(9) . . ?
C6A C7A H7A 121.5 . . ?
C3A C7A H7A 121.5 . . ?
C9A C8A C13A 119.6(8) . . ?
C9A C8A N1A 125.5(7) . . ?
C13A C8A N1A 114.9(7) . . ?
C8A C9A C10A 120.7(9) . . ?
C8A C9A H9A 119.7 . . ?
C10A C9A H9A 119.7 . . ?
C11A C10A C9A 118.3(9) . . ?
C11A C10A H10A 120.8 . . ?
C9A C10A H10A 120.8 . . ?
C12A C11A C10A 123.0(8) . . ?
C12A C11A F1A 119.3(8) . . ?
C10A C11A F1A 117.7(8) . . ?
C11A C12A C13A 117.6(8) . . ?
C11A C12A H12A 121.2 . . ?
C13A C12A H12A 121.2 . . ?
C8A C13A C12A 120.9(8) . . ?
C8A C13A H13A 119.6 . . ?
C12A C13A H13A 119.6 . . ?

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
C1 N2 N3 C2 0.7(10) . . . . ?
N3 N2 C1 N1 179.6(7) . . . . ?
N3 N2 C1 S1 -0.5(9) . . . . ?
C8 N1 C1 N2 -178.9(9) . . . . ?
C8 N1 C1 S1 1.2(14) . . . . ?
C2 S1 C1 N2 0.2(7) . . . . ?
C2 S1 C1 N1 -179.9(8) . . . . ?
N2 N3 C2 C3 -179.1(7) . . . . ?
N2 N3 C2 S1 -0.6(9) . . . . ?
C1 S1 C2 N3 0.2(7) . . . . ?
C1 S1 C2 C3 178.7(7) . . . . ?
C4 N4 C3 C7 2.0(13) . . . . ?
C4 N4 C3 C2 -178.7(7) . . . . ?
N3 C2 C3 N4 -179.3(7) . . . . ?
S1 C2 C3 N4 2.3(10) . . . . ?
N3 C2 C3 C7 0.0(13) . . . . ?
S1 C2 C3 C7 -178.4(7) . . . . ?
C3 N4 C4 C5 -3.0(14) . . . . ?
N4 C4 C5 C6 3.1(16) . . . . ?
C4 C5 C6 C7 -2.1(15) . . . . ?
C5 C6 C7 C3 1.3(14) . . . . ?
N4 C3 C7 C6 -1.2(13) . . . . ?
C2 C3 C7 C6 179.5(8) . . . . ?
C1 N1 C8 C9 11.4(16) . . . . ?
C1 N1 C8 C13 -167.2(9) . . . . ?
N1 C8 C9 C10 -179.2(8) . . . . ?
C13 C8 C9 C10 -0.6(13) . . . . ?
C8 C9 C10 C11 2.4(14) . . . . ?
C9 C10 C11 C12 -3.6(16) . . . . ?
C9 C10 C11 F1 178.8(8) . . . . ?
C10 C11 C12 C13 3.0(17) . . . . ?
F1 C11 C12 C13 -179.4(9) . . . . ?
C11 C12 C13 C8 -1.2(16) . . . . ?
N1 C8 C13 C12 178.7(9) . . . . ?
C9 C8 C13 C12 0.0(14) . . . . ?
C1A N2A N3A C2A -1.0(10) . . . . ?
C8A N1A C1A N2A 177.4(8) . . . . ?
C8A N1A C1A S1A -4.1(14) . . . . ?
N3A N2A C1A N1A 179.1(7) . . . . ?
N3A N2A C1A S1A 0.4(9) . . . . ?
C2A S1A C1A N1A -178.4(8) . . . . ?
C2A S1A C1A N2A 0.2(7) . . . . ?
N2A N3A C2A C3A 179.2(7) . . . . ?
N2A N3A C2A S1A 1.2(9) . . . . ?
C1A S1A C2A N3A -0.8(6) . . . . ?
C1A S1A C2A C3A -178.9(7) . . . . ?
C4A N4A C3A C7A -2.4(13) . . . . ?
C4A N4A C3A C2A 179.4(8) . . . . ?
N3A C2A C3A N4A 179.7(8) . . . . ?
S1A C2A C3A N4A -2.5(11) . . . . ?
N3A C2A C3A C7A 1.4(13) . . . . ?
S1A C2A C3A C7A 179.2(6) . . . . ?
C3A N4A C4A C5A 1.8(15) . . . . ?
N4A C4A C5A C6A -1.0(17) . . . . ?
C4A C5A C6A C7A 0.7(17) . . . . ?
C5A C6A C7A C3A -1.3(15) . . . . ?
N4A C3A C7A C6A 2.2(14) . . . . ?
C2A C3A C7A C6A -179.7(8) . . . . ?
C1A N1A C8A C9A 3.0(15) . . . . ?
C1A N1A C8A C13A -176.3(8) . . . . ?
C13A C8A C9A C10A 0.1(14) . . . . ?
N1A C8A C9A C10A -179.1(8) . . . . ?
C8A C9A C10A C11A 0.3(15) . . . . ?
C9A C10A C11A C12A -0.3(16) . . . . ?
C9A C10A C11A F1A 179.7(8) . . . . ?
C10A C11A C12A C13A -0.2(15) . . . . ?
F1A C11A C12A C13A 179.8(8) . . . . ?
C9A C8A C13A C12A -0.7(14) . . . . ?
N1A C8A C13A C12A 178.7(8) . . . . ?
C11A C12A C13A C8A 0.7(14) . . . . ?

_refine_diff_density_max         0.559
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1825055'
_audit_update_record             
;
2018-02-21 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 F N4 O2 S V'
_chemical_formula_sum            'C14 H12 F N4 O2 S V'
_chemical_formula_weight         370.28

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'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   19.600(3)
_cell_length_b                   14.7000(8)
_cell_length_c                   14.922(2)
_cell_angle_alpha                90
_cell_angle_beta                 134.83(3)
_cell_angle_gamma                90
_cell_volume                     3049.1(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3273
_cell_measurement_theta_min      2.7333
_cell_measurement_theta_max      29.2894

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.812
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60999
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2012)'
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measurement_method       'ω scan'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12030
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.739
_diffrn_reflns_theta_max         29.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3723
_reflns_number_gt                2247
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL2014/7 (Sheldrick, 2015)'
_refine_special_details          
;
Carbon-bound H-atoms were placed in calculated positions [C---H 0.93-0.96 %A,
Uiso(H) 1.2-1.5Ueq(C)] and were included in the refinement 
in the riding model approximation.
The N---H atom was refined with N---H = 0.88+-0.01 Å.
Statistical disorder was noted in the fluorobenzene ring and this was refined
over two sites as idealised hexagons and with matching pairs of atoms having
their anisotropic displacement parameters tied.
The following atoms were refined to restrain their ADP's to be approximately
isotropic: C1, C2, C3, C4, C5 & C6.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+3.1385P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3723
_refine_ls_number_parameters     210
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.007
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V V 0.63134(4) 0.31397(4) 0.70273(5) 0.0546(2) Uani 1 1 d . . . . .
S1 S 0.47221(7) 0.27425(6) 0.59559(11) 0.0789(3) Uani 1 1 d . . . . .
F1 F 0.0984(8) 0.6763(7) 0.3840(14) 0.110(3) Uani 0.5 1 d . . P A 1
F1' F 0.0721(8) 0.6373(7) 0.3828(14) 0.110(3) Uani 0.5 1 d . . P A 2
O1 O 0.69357(17) 0.25778(18) 0.8323(2) 0.0756(7) Uani 1 1 d . . . . .
O2 O 0.6361(2) 0.2654(2) 0.6116(3) 0.0904(9) Uani 1 1 d . . . . .
N1 N 0.33382(19) 0.3836(2) 0.5155(3) 0.0632(8) Uani 1 1 d D . . . .
H1N H 0.311(3) 0.3282(12) 0.496(4) 0.090(14) Uiso 1 1 d D . . . .
N2 N 0.47369(18) 0.45804(18) 0.6088(2) 0.0558(7) Uani 1 1 d . . . . .
N3 N 0.56626(17) 0.44403(18) 0.6653(2) 0.0527(6) Uani 1 1 d . . . . .
N4 N 0.73635(19) 0.4105(2) 0.7697(2) 0.0633(8) Uani 1 1 d . . . . .
C1 C 0.2740(9) 0.4604(7) 0.4753(16) 0.055(2) Uani 0.5 1 d DG U P A 1
C2 C 0.1856(9) 0.4451(4) 0.4344(16) 0.0611(17) Uani 0.5 1 d G U P A 1
H2 H 0.1650 0.3860 0.4262 0.073 Uiso 0.5 1 calc R U P A 1
C3 C 0.1281(6) 0.5183(5) 0.4059(12) 0.069(2) Uani 0.5 1 d G U P A 1
H3 H 0.0690 0.5081 0.3785 0.083 Uiso 0.5 1 calc R U P A 1
C4 C 0.1590(5) 0.6067(4) 0.4182(10) 0.064(2) Uani 0.5 1 d G U P A 1
C5 C 0.2473(6) 0.6220(6) 0.4591(11) 0.070(2) Uani 0.5 1 d G U P A 1
H5 H 0.2680 0.6812 0.4674 0.084 Uiso 0.5 1 calc R U P A 1
C6 C 0.3048(6) 0.5488(9) 0.4877(13) 0.061(2) Uani 0.5 1 d G U P A 1
H6 H 0.3640 0.5590 0.5150 0.074 Uiso 0.5 1 calc R U P A 1
C7 C 0.4269(2) 0.3817(2) 0.5748(3) 0.0537(8) Uani 1 1 d . . . . .
C8 C 0.6179(2) 0.5173(2) 0.7011(3) 0.0575(9) Uani 1 1 d . . . . .
C9 C 0.5823(3) 0.6104(2) 0.6866(4) 0.0796(12) Uani 1 1 d . . . . .
H9A H 0.5455 0.6102 0.7070 0.119 Uiso 1 1 calc R U . . .
H9B H 0.5423 0.6303 0.6010 0.119 Uiso 1 1 calc R U . . .
H9C H 0.6359 0.6511 0.7426 0.119 Uiso 1 1 calc R U . . .
C10 C 0.7142(2) 0.4994(3) 0.7565(3) 0.0618(9) Uani 1 1 d . . . . .
C11 C 0.7795(3) 0.5658(3) 0.7911(3) 0.0828(13) Uani 1 1 d . . . . .
H11 H 0.7641 0.6271 0.7824 0.099 Uiso 1 1 calc R U . . .
C12 C 0.8671(3) 0.5398(4) 0.8384(4) 0.0955(15) Uani 1 1 d . . . . .
H12 H 0.9110 0.5836 0.8603 0.115 Uiso 1 1 calc R U . . .
C13 C 0.8895(3) 0.4505(4) 0.8531(4) 0.0919(15) Uani 1 1 d . . . . .
H13 H 0.9490 0.4324 0.8861 0.110 Uiso 1 1 calc R U . . .
C14 C 0.8227(3) 0.3863(3) 0.8186(3) 0.0779(11) Uani 1 1 d . . . . .
H14 H 0.8383 0.3248 0.8296 0.094 Uiso 1 1 calc R U . . .
C1' C 0.2745(8) 0.4518(7) 0.4936(16) 0.055(2) Uani 0.5 1 d DG . P A 2
C2' C 0.1868(10) 0.4213(4) 0.4458(16) 0.0611(17) Uani 0.5 1 d G . P A 2
H2' H 0.1754 0.3593 0.4412 0.073 Uiso 0.5 1 calc R U P A 2
C3' C 0.1163(6) 0.4836(5) 0.4049(12) 0.069(2) Uani 0.5 1 d G . P A 2
H3' H 0.0577 0.4632 0.3729 0.083 Uiso 0.5 1 calc R U P A 2
C4' C 0.1334(4) 0.5763(4) 0.4118(9) 0.064(2) Uani 0.5 1 d G . P A 2
C5' C 0.2211(6) 0.6068(5) 0.4596(11) 0.070(2) Uani 0.5 1 d G . P A 2
H5' H 0.2325 0.6688 0.4642 0.084 Uiso 0.5 1 calc R U P A 2
C6' C 0.2916(6) 0.5445(8) 0.5005(13) 0.061(2) Uani 0.5 1 d G . P A 2
H6' H 0.3502 0.5648 0.5325 0.074 Uiso 0.5 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V O2 1.596(3) . ?
V O1 1.607(2) . ?
V N4 2.085(3) . ?
V N3 2.142(3) . ?
V S1 2.3652(13) . ?
S1 C7 1.730(3) . ?
F1 C4 1.364(13) . ?
F1' C4' 1.305(13) . ?
N1 C7 1.355(4) . ?
N1 C1' 1.388(6) . ?
N1 C1 1.420(6) . ?
N1 H1N 0.877(10) . ?
N2 C7 1.305(4) . ?
N2 N3 1.374(4) . ?
N3 C8 1.307(4) . ?
N4 C14 1.335(5) . ?
N4 C10 1.346(5) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C10 1.455(5) . ?
C8 C9 1.482(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.387(5) . ?
C11 C12 1.373(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.352(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C1' C2' 1.3900 . ?
C1' C6' 1.3900 . ?
C2' C3' 1.3900 . ?
C2' H2' 0.9300 . ?
C3' C4' 1.3900 . ?
C3' H3' 0.9300 . ?
C4' C5' 1.3900 . ?
C5' C6' 1.3900 . ?
C5' H5' 0.9300 . ?
C6' H6' 0.9300 . ?

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
O2 V O1 110.14(16) . . ?
O2 V N4 94.70(14) . . ?
O1 V N4 96.77(12) . . ?
O2 V N3 123.99(13) . . ?
O1 V N3 125.43(12) . . ?
N4 V N3 73.90(11) . . ?
O2 V S1 98.93(11) . . ?
O1 V S1 101.94(10) . . ?
N4 V S1 151.35(10) . . ?
N3 V S1 77.58(7) . . ?
C7 S1 V 99.31(11) . . ?
C7 N1 C1' 133.4(7) . . ?
C7 N1 C1 128.5(7) . . ?
C7 N1 H1N 110(3) . . ?
C1' N1 H1N 116(3) . . ?
C1 N1 H1N 121(3) . . ?
C7 N2 N3 111.8(3) . . ?
C8 N3 N2 115.8(3) . . ?
C8 N3 V 118.8(2) . . ?
N2 N3 V 125.42(19) . . ?
C14 N4 C10 119.5(3) . . ?
C14 N4 V 121.5(3) . . ?
C10 N4 V 118.9(2) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 N1 117.3(9) . . ?
C6 C1 N1 122.3(9) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
F1 C4 C5 121.9(6) . . ?
F1 C4 C3 118.0(6) . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N2 C7 N1 119.4(3) . . ?
N2 C7 S1 125.7(3) . . ?
N1 C7 S1 114.9(2) . . ?
N3 C8 C10 113.9(3) . . ?
N3 C8 C9 123.5(3) . . ?
C10 C8 C9 122.6(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 C11 120.8(4) . . ?
N4 C10 C8 114.4(3) . . ?
C11 C10 C8 124.8(4) . . ?
C12 C11 C10 119.1(5) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 119.9(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.2(4) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N4 C14 C13 121.5(5) . . ?
N4 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
N1 C1' C2' 114.6(9) . . ?
N1 C1' C6' 124.9(10) . . ?
C2' C1' C6' 120.0 . . ?
C3' C2' C1' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
C1' C2' H2' 120.0 . . ?
C4' C3' C2' 120.0 . . ?
C4' C3' H3' 120.0 . . ?
C2' C3' H3' 120.0 . . ?
F1' C4' C3' 122.1(6) . . ?
F1' C4' C5' 117.7(6) . . ?
C3' C4' C5' 120.0 . . ?
C6' C5' C4' 120.0 . . ?
C6' C5' H5' 120.0 . . ?
C4' C5' H5' 120.0 . . ?
C5' C6' C1' 120.0 . . ?
C5' C6' H6' 120.0 . . ?
C1' C6' H6' 120.0 . . ?

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 N2 N3 C8 179.3(3) . . . . ?
C7 N2 N3 V -2.6(3) . . . . ?
C7 N1 C1 C2 -170.1(6) . . . . ?
C7 N1 C1 C6 3.4(15) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
N1 C1 C2 C3 173.6(13) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 F1 177.2(12) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
F1 C4 C5 C6 -177.1(12) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
N1 C1 C6 C5 -173.3(14) . . . . ?
N3 N2 C7 N1 -178.8(3) . . . . ?
N3 N2 C7 S1 -0.2(4) . . . . ?
C1' N1 C7 N2 -10.0(11) . . . . ?
C1 N1 C7 N2 4.6(10) . . . . ?
C1' N1 C7 S1 171.2(10) . . . . ?
C1 N1 C7 S1 -174.2(9) . . . . ?
V S1 C7 N2 2.2(3) . . . . ?
V S1 C7 N1 -179.1(2) . . . . ?
N2 N3 C8 C10 -178.0(2) . . . . ?
V N3 C8 C10 3.8(3) . . . . ?
N2 N3 C8 C9 1.7(4) . . . . ?
V N3 C8 C9 -176.5(3) . . . . ?
C14 N4 C10 C11 1.1(5) . . . . ?
V N4 C10 C11 -175.2(3) . . . . ?
C14 N4 C10 C8 179.5(3) . . . . ?
V N4 C10 C8 3.2(4) . . . . ?
N3 C8 C10 N4 -4.5(4) . . . . ?
C9 C8 C10 N4 175.8(3) . . . . ?
N3 C8 C10 C11 173.8(3) . . . . ?
C9 C8 C10 C11 -5.9(5) . . . . ?
N4 C10 C11 C12 0.5(5) . . . . ?
C8 C10 C11 C12 -177.7(3) . . . . ?
C10 C11 C12 C13 -1.4(6) . . . . ?
C11 C12 C13 C14 0.8(6) . . . . ?
C10 N4 C14 C13 -1.7(5) . . . . ?
V N4 C14 C13 174.4(3) . . . . ?
C12 C13 C14 N4 0.8(6) . . . . ?
C7 N1 C1' C2' -170.1(6) . . . . ?
C7 N1 C1' C6' 18.6(17) . . . . ?
N1 C1' C2' C3' -171.8(13) . . . . ?
C6' C1' C2' C3' 0.0 . . . . ?
C1' C2' C3' C4' 0.0 . . . . ?
C2' C3' C4' F1' -175.1(13) . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
F1' C4' C5' C6' 175.4(12) . . . . ?
C3' C4' C5' C6' 0.0 . . . . ?
C4' C5' C6' C1' 0.0 . . . . ?
N1 C1' C6' C5' 170.9(14) . . . . ?
C2' C1' C6' C5' 0.0 . . . . ?

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.056

