# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_170721praj
_database_code_depnum_ccdc_archive 'CCDC 1823578'
_audit_update_record             
;
2018-02-12 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H14 Br2 F4 N4 S'
_chemical_formula_moiety         'C20 H14 Br2 F4 N4 S'
_chemical_formula_weight         578.22
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.8145(2)
_cell_length_b                   12.6491(2)
_cell_length_c                   11.5796(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.7090
_cell_angle_gamma                90.0000
_cell_volume                     2078.28(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16094
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.45
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136.00
_exptl_absorpt_coefficient_mu    4.064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_T_max  0.816

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            19950
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4728
_reflns_number_gt                4066
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0739
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4728
_refine_ls_number_parameters     280
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0355P)²+0.9383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.770
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br1 Br 0.86065(2) -0.07510(2) 0.78341(2) 0.04807(9) Uani 1.0 4 d . . .
Br2 Br 0.57673(2) -0.57283(2) 1.41519(2) 0.03965(8) Uani 1.0 4 d . . .
S1 S 0.74699(3) -0.10826(4) 1.41062(4) 0.02078(11) Uani 1.0 4 d . . .
F1 F 0.78700(8) -0.14403(9) 1.30134(10) 0.0266(3) Uani 1.0 4 d . . .
F2 F 0.65077(8) -0.06863(9) 1.31515(10) 0.0265(3) Uani 1.0 4 d . . .
F3 F 0.70771(8) -0.07045(9) 1.51995(10) 0.0258(3) Uani 1.0 4 d . . .
F4 F 0.84481(8) -0.14572(9) 1.50751(10) 0.0274(3) Uani 1.0 4 d . . .
N1 N 0.84043(14) 0.18911(15) 1.44234(17) 0.0332(4) Uani 1.0 4 d . . .
N2 N 0.90336(13) 0.14316(15) 1.39929(17) 0.0331(4) Uani 1.0 4 d . . .
N3 N 0.87945(12) 0.04054(14) 1.37940(15) 0.0251(4) Uani 1.0 4 d . . .
N4 N 0.66154(12) -0.28741(14) 1.31131(15) 0.0255(4) Uani 1.0 4 d . . .
C1 C 0.72482(16) 0.18753(18) 1.6216(2) 0.0335(5) Uani 1.0 4 d . . .
C2 C 0.65645(18) 0.2149(2) 1.6763(3) 0.0410(6) Uani 1.0 4 d . . .
C3 C 0.56217(18) 0.2038(2) 1.6151(3) 0.0402(6) Uani 1.0 4 d . . .
C4 C 0.53579(17) 0.16621(19) 1.4983(3) 0.0388(6) Uani 1.0 4 d . . .
C5 C 0.60371(16) 0.13767(18) 1.4430(2) 0.0331(5) Uani 1.0 4 d . . .
C6 C 0.69892(15) 0.14723(16) 1.50462(19) 0.0264(5) Uani 1.0 4 d . . .
C7 C 0.77452(15) 0.11646(16) 1.45138(18) 0.0261(5) Uani 1.0 4 d . . .
C8 C 0.79899(14) 0.02114(16) 1.41028(17) 0.0232(4) Uani 1.0 4 d . . .
C9 C 0.94478(14) -0.02536(18) 1.33459(18) 0.0282(5) Uani 1.0 4 d . . .
C10 C 0.91748(14) -0.03763(17) 1.19944(18) 0.0246(4) Uani 1.0 4 d . . .
C11 C 0.94968(15) -0.12605(17) 1.1518(2) 0.0300(5) Uani 1.0 4 d . . .
C12 C 0.93459(16) -0.13650(18) 1.0284(2) 0.0323(5) Uani 1.0 4 d . . .
C13 C 0.88498(15) -0.05846(18) 0.95299(19) 0.0311(5) Uani 1.0 4 d . . .
C14 C 0.85231(16) 0.03016(19) 0.9975(2) 0.0334(5) Uani 1.0 4 d . . .
C15 C 0.86921(15) 0.04031(18) 1.1218(2) 0.0301(5) Uani 1.0 4 d . . .
C16 C 0.69659(13) -0.24083(15) 1.41659(17) 0.0218(4) Uani 1.0 4 d . . .
C17 C 0.69853(14) -0.28308(16) 1.52771(18) 0.0259(4) Uani 1.0 4 d . . .
C18 C 0.66046(15) -0.38323(17) 1.52748(18) 0.0278(5) Uani 1.0 4 d . . .
C19 C 0.62506(15) -0.43415(16) 1.4187(2) 0.0269(5) Uani 1.0 4 d . . .
C20 C 0.62676(15) -0.38544(17) 1.31276(18) 0.0276(5) Uani 1.0 4 d . . .
H1 H 0.7896 0.1962 1.6640 0.0402 Uiso 1.0 4 calc R . .
H2 H 0.6745 0.2416 1.7564 0.0492 Uiso 1.0 4 calc R . .
H3 H 0.5155 0.2220 1.6534 0.0483 Uiso 1.0 4 calc R . .
H4 H 0.4709 0.1598 1.4556 0.0466 Uiso 1.0 4 calc R . .
H5 H 0.5851 0.1115 1.3627 0.0397 Uiso 1.0 4 calc R . .
H9A H 0.9484 -0.0964 1.3715 0.0338 Uiso 1.0 4 calc R . .
H9B H 1.0085 0.0063 1.3619 0.0338 Uiso 1.0 4 calc R . .
H11 H 0.9824 -0.1800 1.2044 0.0359 Uiso 1.0 4 calc R . .
H12 H 0.9579 -0.1963 0.9963 0.0388 Uiso 1.0 4 calc R . .
H14 H 0.8188 0.0834 0.9443 0.0400 Uiso 1.0 4 calc R . .
H15 H 0.8474 0.1013 1.1536 0.0361 Uiso 1.0 4 calc R . .
H17 H 0.7247 -0.2452 1.6005 0.0310 Uiso 1.0 4 calc R . .
H18 H 0.6588 -0.4160 1.6007 0.0333 Uiso 1.0 4 calc R . .
H20 H 0.6027 -0.4222 1.2387 0.0331 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C13 1.903(3) yes . .
Br2 C19 1.891(2) yes . .
S1 F1 1.6089(14) yes . .
S1 F2 1.6122(11) yes . .
S1 F3 1.6105(14) yes . .
S1 F4 1.6274(11) yes . .
S1 C8 1.809(2) yes . .
S1 C16 1.845(2) yes . .
N1 N2 1.313(3) yes . .
N1 C7 1.367(3) yes . .
N2 N3 1.348(3) yes . .
N3 C8 1.362(3) yes . .
N3 C9 1.480(3) yes . .
N4 C16 1.319(3) yes . .
N4 C20 1.345(3) yes . .
C1 C2 1.384(4) yes . .
C1 C6 1.394(3) yes . .
C2 C3 1.380(4) yes . .
C3 C4 1.380(4) yes . .
C4 C5 1.387(4) yes . .
C5 C6 1.391(3) yes . .
C6 C7 1.477(4) yes . .
C7 C8 1.382(3) yes . .
C9 C10 1.508(3) yes . .
C10 C11 1.391(4) yes . .
C10 C15 1.386(3) yes . .
C11 C12 1.388(4) yes . .
C12 C13 1.381(3) yes . .
C13 C14 1.378(4) yes . .
C14 C15 1.394(4) yes . .
C16 C17 1.386(3) yes . .
C17 C18 1.386(3) yes . .
C18 C19 1.377(3) yes . .
C19 C20 1.380(4) yes . .
C1 H1 0.950 no . .
C2 H2 0.950 no . .
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C5 H5 0.950 no . .
C9 H9A 0.990 no . .
C9 H9B 0.990 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .
C14 H14 0.950 no . .
C15 H15 0.950 no . .
C17 H17 0.950 no . .
C18 H18 0.950 no . .
C20 H20 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
F1 S1 F2 90.07(7) yes . . .
F1 S1 F3 179.01(7) yes . . .
F1 S1 F4 90.23(7) yes . . .
F1 S1 C8 89.96(9) yes . . .
F1 S1 C16 91.06(9) yes . . .
F2 S1 F3 89.92(7) yes . . .
F2 S1 F4 178.81(7) yes . . .
F2 S1 C8 90.59(8) yes . . .
F2 S1 C16 91.19(7) yes . . .
F3 S1 F4 89.77(7) yes . . .
F3 S1 C8 89.05(9) yes . . .
F3 S1 C16 89.94(9) yes . . .
F4 S1 C8 88.26(8) yes . . .
F4 S1 C16 89.96(7) yes . . .
C8 S1 C16 177.95(9) yes . . .
N2 N1 C7 109.42(19) yes . . .
N1 N2 N3 108.11(19) yes . . .
N2 N3 C8 109.61(18) yes . . .
N2 N3 C9 115.86(19) yes . . .
C8 N3 C9 134.49(18) yes . . .
C16 N4 C20 116.80(18) yes . . .
C2 C1 C6 120.2(2) yes . . .
C1 C2 C3 120.4(3) yes . . .
C2 C3 C4 119.8(3) yes . . .
C3 C4 C5 120.3(3) yes . . .
C4 C5 C6 120.2(3) yes . . .
C1 C6 C5 119.1(3) yes . . .
C1 C6 C7 118.16(19) yes . . .
C5 C6 C7 122.8(2) yes . . .
N1 C7 C6 119.92(19) yes . . .
N1 C7 C8 107.2(2) yes . . .
C6 C7 C8 132.7(2) yes . . .
S1 C8 N3 124.68(16) yes . . .
S1 C8 C7 129.37(18) yes . . .
N3 C8 C7 105.62(19) yes . . .
N3 C9 C10 114.50(16) yes . . .
C9 C10 C11 118.32(18) yes . . .
C9 C10 C15 122.3(2) yes . . .
C11 C10 C15 119.1(2) yes . . .
C10 C11 C12 120.9(2) yes . . .
C11 C12 C13 118.8(3) yes . . .
Br1 C13 C12 118.78(18) yes . . .
Br1 C13 C14 119.52(16) yes . . .
C12 C13 C14 121.7(2) yes . . .
C13 C14 C15 118.9(2) yes . . .
C10 C15 C14 120.7(3) yes . . .
S1 C16 N4 115.31(16) yes . . .
S1 C16 C17 118.99(14) yes . . .
N4 C16 C17 125.70(19) yes . . .
C16 C17 C18 116.79(18) yes . . .
C17 C18 C19 118.5(2) yes . . .
Br2 C19 C18 119.74(18) yes . . .
Br2 C19 C20 119.91(16) yes . . .
C18 C19 C20 120.3(2) yes . . .
N4 C20 C19 121.86(19) yes . . .
C2 C1 H1 119.913 no . . .
C6 C1 H1 119.905 no . . .
C1 C2 H2 119.791 no . . .
C3 C2 H2 119.803 no . . .
C2 C3 H3 120.077 no . . .
C4 C3 H3 120.080 no . . .
C3 C4 H4 119.870 no . . .
C5 C4 H4 119.875 no . . .
C4 C5 H5 119.877 no . . .
C6 C5 H5 119.884 no . . .
N3 C9 H9A 108.631 no . . .
N3 C9 H9B 108.637 no . . .
C10 C9 H9A 108.640 no . . .
C10 C9 H9B 108.640 no . . .
H9A C9 H9B 107.581 no . . .
C10 C11 H11 119.566 no . . .
C12 C11 H11 119.563 no . . .
C11 C12 H12 120.605 no . . .
C13 C12 H12 120.605 no . . .
C13 C14 H14 120.572 no . . .
C15 C14 H14 120.576 no . . .
C10 C15 H15 119.665 no . . .
C14 C15 H15 119.658 no . . .
C16 C17 H17 121.607 no . . .
C18 C17 H17 121.603 no . . .
C17 C18 H18 120.757 no . . .
C19 C18 H18 120.756 no . . .
N4 C20 H20 119.074 no . . .
C19 C20 H20 119.062 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
F1 S1 C8 N3 -31.15(14) no . . . .
F1 S1 C8 C7 156.48(15) no . . . .
F1 S1 C16 N4 -36.73(13) no . . . .
F1 S1 C16 C17 143.04(13) no . . . .
F2 S1 C8 N3 -121.22(14) no . . . .
F2 S1 C8 C7 66.41(15) no . . . .
F2 S1 C16 N4 53.36(14) no . . . .
F2 S1 C16 C17 -126.87(14) no . . . .
F3 S1 C8 N3 148.87(14) no . . . .
F3 S1 C8 C7 -23.50(15) no . . . .
F3 S1 C16 N4 143.28(13) no . . . .
F3 S1 C16 C17 -36.95(14) no . . . .
F4 S1 C8 N3 59.07(14) no . . . .
F4 S1 C8 C7 -113.29(15) no . . . .
F4 S1 C16 N4 -126.95(14) no . . . .
F4 S1 C16 C17 52.82(14) no . . . .
N2 N1 C7 C6 176.31(15) no . . . .
N2 N1 C7 C8 -0.5(2) no . . . .
C7 N1 N2 N3 0.2(2) no . . . .
N1 N2 N3 C8 0.24(19) no . . . .
N1 N2 N3 C9 -177.84(13) no . . . .
N2 N3 C8 S1 -174.42(13) no . . . .
N2 N3 C8 C7 -0.54(19) no . . . .
N2 N3 C9 C10 -95.22(19) no . . . .
C8 N3 C9 C10 87.3(3) no . . . .
C9 N3 C8 S1 3.2(3) no . . . .
C9 N3 C8 C7 177.04(17) no . . . .
C16 N4 C20 C19 1.9(3) no . . . .
C20 N4 C16 S1 178.09(16) no . . . .
C20 N4 C16 C17 -1.7(3) no . . . .
C2 C1 C6 C5 1.6(4) no . . . .
C2 C1 C6 C7 -178.4(2) no . . . .
C6 C1 C2 C3 -0.7(4) no . . . .
C1 C2 C3 C4 -0.7(4) no . . . .
C2 C3 C4 C5 1.2(4) no . . . .
C3 C4 C5 C6 -0.3(4) no . . . .
C4 C5 C6 C1 -1.1(4) no . . . .
C4 C5 C6 C7 178.93(19) no . . . .
C1 C6 C7 N1 -57.6(3) no . . . .
C1 C6 C7 C8 118.3(3) no . . . .
C5 C6 C7 N1 122.4(2) no . . . .
C5 C6 C7 C8 -61.7(3) no . . . .
N1 C7 C8 S1 174.11(14) no . . . .
N1 C7 C8 N3 0.62(19) no . . . .
C6 C7 C8 S1 -2.1(4) no . . . .
C6 C7 C8 N3 -175.62(18) no . . . .
N3 C9 C10 C11 -155.50(17) no . . . .
N3 C9 C10 C15 30.6(3) no . . . .
C9 C10 C11 C12 -173.70(18) no . . . .
C9 C10 C15 C14 174.41(18) no . . . .
C11 C10 C15 C14 0.5(4) no . . . .
C15 C10 C11 C12 0.4(4) no . . . .
C10 C11 C12 C13 -1.5(4) no . . . .
C11 C12 C13 Br1 -177.93(18) no . . . .
C11 C12 C13 C14 1.6(4) no . . . .
Br1 C13 C14 C15 178.85(14) no . . . .
C12 C13 C14 C15 -0.6(4) no . . . .
C13 C14 C15 C10 -0.4(4) no . . . .
S1 C16 C17 C18 -179.51(12) no . . . .
N4 C16 C17 C18 0.2(3) no . . . .
C16 C17 C18 C19 1.0(3) no . . . .
C17 C18 C19 Br2 177.71(17) no . . . .
C17 C18 C19 C20 -0.7(4) no . . . .
Br2 C19 C20 N4 -179.19(14) no . . . .
C18 C19 C20 N4 -0.7(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 C6 3.547(3) no . .
S1 C9 3.456(3) no . .
F1 N3 2.726(2) no . .
F1 N4 2.623(3) no . .
F1 C9 2.711(3) no . .
F1 C10 2.873(3) no . .
F1 C11 3.355(3) no . .
F1 C15 3.564(3) no . .
F2 N3 3.534(2) no . .
F2 N4 2.773(2) no . .
F2 C5 3.175(3) no . .
F2 C6 3.446(3) no . .
F2 C7 3.109(3) no . .
F2 C17 3.594(3) no . .
F3 N4 3.590(2) no . .
F3 C1 3.454(3) no . .
F3 C5 3.051(3) no . .
F3 C6 2.760(3) no . .
F3 C7 2.766(3) no . .
F3 C17 2.696(3) no . .
F4 N3 2.907(3) no . .
F4 N4 3.4926(19) no . .
F4 C7 3.481(3) no . .
F4 C9 3.198(3) no . .
F4 C17 2.839(3) no . .
N1 C1 3.048(4) no . .
N1 C5 3.569(4) no . .
N1 C9 3.524(3) no . .
N2 C6 3.576(4) no . .
N2 C10 3.303(3) no . .
N2 C15 3.367(3) no . .
N3 C15 2.943(3) no . .
N4 C18 2.785(3) no . .
C1 C4 2.767(3) no . .
C2 C5 2.766(4) no . .
C3 C6 2.783(4) no . .
C5 C8 3.364(4) no . .
C8 C10 3.473(4) no . .
C10 C13 2.767(3) no . .
C11 C14 2.774(3) no . .
C12 C15 2.777(4) no . .
C16 C19 2.668(3) no . .
C17 C20 2.735(3) no . .
Br1 F3 3.2357(11) no . 1_554
Br1 F4 3.2602(12) no . 1_554
Br1 N4 3.5182(19) no . 4_544
Br1 C10 3.536(3) no . 3_757
Br2 C4 3.539(3) no . 1_545
F1 C17 3.197(3) no . 4_544
F1 C18 3.205(3) no . 4_544
F2 C18 3.430(3) no . 4_544
F3 Br1 3.2357(11) no . 1_556
F4 Br1 3.2602(12) no . 1_556
F4 N2 3.573(3) no . 3_758
F4 C11 3.471(3) no . 4_545
F4 C12 3.038(3) no . 4_545
N2 F4 3.573(3) no . 3_758
N2 C9 3.576(3) no . 3_758
N3 C9 3.581(3) no . 3_758
N4 Br1 3.5182(19) no . 4_545
N4 C17 3.594(3) no . 4_544
C4 Br2 3.539(3) no . 1_565
C9 N2 3.576(3) no . 3_758
C9 N3 3.581(3) no . 3_758
C10 Br1 3.536(3) no . 3_757
C11 F4 3.471(3) no . 4_544
C12 F4 3.038(3) no . 4_544
C12 C13 3.597(4) no . 3_757
C12 C14 3.523(4) no . 3_757
C13 C12 3.597(4) no . 3_757
C13 C13 3.585(3) no . 3_757
C14 C12 3.523(4) no . 3_757
C14 C18 3.496(4) no . 4_544
C14 C19 3.446(4) no . 4_544
C15 C18 3.572(3) no . 4_544
C17 F1 3.197(3) no . 4_545
C17 N4 3.594(3) no . 4_545
C18 F1 3.205(3) no . 4_545
C18 F2 3.430(3) no . 4_545
C18 C14 3.496(4) no . 4_545
C18 C15 3.572(3) no . 4_545
C19 C14 3.446(4) no . 4_545
Br1 H12 2.9088 no . .
Br1 H14 2.9222 no . .
Br2 H18 2.9201 no . .
Br2 H20 2.8991 no . .
S1 H9A 3.1473 no . .
S1 H17 2.8922 no . .
F1 H9A 2.3708 no . .
F1 H11 3.4232 no . .
F2 H5 2.5977 no . .
F3 H5 3.1637 no . .
F3 H17 2.3848 no . .
F4 H9A 2.5716 no . .
F4 H17 2.6484 no . .
N1 H1 2.8764 no . .
N1 H15 3.5531 no . .
N2 H9A 3.1393 no . .
N2 H9B 2.4488 no . .
N2 H15 2.7761 no . .
N3 H15 2.6341 no . .
N4 H17 3.2518 no . .
C1 H3 3.2550 no . .
C1 H5 3.2604 no . .
C2 H4 3.2454 no . .
C3 H1 3.2534 no . .
C3 H5 3.2551 no . .
C4 H2 3.2450 no . .
C5 H1 3.2600 no . .
C5 H3 3.2574 no . .
C6 H2 3.2644 no . .
C6 H4 3.2650 no . .
C7 H1 2.6099 no . .
C7 H5 2.6970 no . .
C8 H5 3.2625 no . .
C8 H9A 2.8075 no . .
C8 H9B 3.3140 no . .
C8 H15 3.4063 no . .
C9 H11 2.6256 no . .
C9 H15 2.7019 no . .
C10 H12 3.2754 no . .
C10 H14 3.2747 no . .
C11 H9A 2.5772 no . .
C11 H9B 2.8747 no . .
C11 H15 3.2528 no . .
C12 H14 3.2657 no . .
C13 H11 3.2414 no . .
C13 H15 3.2450 no . .
C14 H12 3.2654 no . .
C15 H9A 3.2829 no . .
C15 H9B 2.9788 no . .
C15 H11 3.2515 no . .
C16 H18 3.2329 no . .
C16 H20 3.1294 no . .
C18 H20 3.2419 no . .
C19 H17 3.2455 no . .
C20 H18 3.2528 no . .
H1 H2 2.3294 no . .
H2 H3 2.3278 no . .
H3 H4 2.3297 no . .
H4 H5 2.3335 no . .
H9A H11 2.3828 no . .
H9A H15 3.5617 no . .
H9B H11 2.9371 no . .
H9B H15 3.1054 no . .
H11 H12 2.3403 no . .
H14 H15 2.3478 no . .
H17 H18 2.3701 no . .
Br1 H9B 3.0364 no . 3_757
Br1 H17 3.2742 no . 1_554
Br2 H2 3.4016 no . 4_544
Br2 H3 3.4636 no . 4_544
Br2 H14 3.5074 no . 4_545
Br2 H18 3.4443 no . 3_648
S1 H18 3.4619 no . 4_544
F1 H12 3.5079 no . 4_545
F1 H17 2.6432 no . 4_544
F1 H18 2.6539 no . 4_544
F2 H3 3.2378 no . 3_658
F2 H18 2.5278 no . 4_544
F3 H4 2.9642 no . 3_658
F3 H20 3.3339 no . 4_545
F4 H9B 2.8684 no . 3_758
F4 H11 3.3972 no . 4_545
F4 H12 2.6357 no . 4_545
N1 H1 3.4155 no . 4_554
N1 H2 2.8988 no . 4_554
N1 H9A 3.4544 no . 3_758
N1 H12 3.2107 no . 2_757
N1 H14 2.8959 no . 4_555
N1 H15 3.5889 no . 4_555
N2 H1 3.4284 no . 4_554
N2 H9A 2.9778 no . 3_758
N2 H9B 3.2944 no . 3_758
N2 H11 3.2366 no . 2_757
N2 H12 2.8950 no . 2_757
N3 H9A 3.3311 no . 3_758
N3 H9B 3.0369 no . 3_758
N4 H3 2.8893 no . 3_658
N4 H4 3.2189 no . 2_647
N4 H17 2.8838 no . 4_544
N4 H18 3.5373 no . 4_544
C1 H15 3.1917 no . 4_555
C2 H5 3.4509 no . 4_555
C4 H20 3.1232 no . 2_657
C5 H2 3.0675 no . 4_554
C5 H20 3.2633 no . 2_657
C6 H2 3.1269 no . 4_554
C7 H2 2.9318 no . 4_554
C8 H9B 3.2998 no . 3_758
C9 H9B 3.3899 no . 3_758
C14 H12 3.4934 no . 3_757
C15 H18 3.4364 no . 4_544
C16 H3 3.0203 no . 3_658
C16 H4 3.3916 no . 3_658
C17 H3 3.3502 no . 3_658
C17 H4 3.0072 no . 3_658
C18 H3 3.4927 no . 3_658
C18 H4 3.4680 no . 3_658
C19 H3 3.3515 no . 3_658
C19 H14 3.3771 no . 4_545
C20 H3 3.0568 no . 3_658
C20 H4 3.0813 no . 2_647
C20 H5 3.2118 no . 2_647
C20 H17 3.5954 no . 4_544
H1 N1 3.4155 no . 4_555
H1 N2 3.4284 no . 4_555
H1 H11 3.2881 no . 3_758
H1 H14 3.4572 no . 1_556
H1 H15 2.7151 no . 4_555
H2 Br2 3.4016 no . 4_545
H2 N1 2.8988 no . 4_555
H2 C5 3.0675 no . 4_555
H2 C6 3.1269 no . 4_555
H2 C7 2.9318 no . 4_555
H2 H5 2.7684 no . 4_555
H2 H14 3.2610 no . 1_556
H3 Br2 3.4636 no . 4_545
H3 F2 3.2378 no . 3_658
H3 N4 2.8893 no . 3_658
H3 C16 3.0203 no . 3_658
H3 C17 3.3502 no . 3_658
H3 C18 3.4927 no . 3_658
H3 C19 3.3515 no . 3_658
H3 C20 3.0568 no . 3_658
H3 H5 3.1522 no . 4_555
H3 H20 3.5064 no . 3_658
H4 F3 2.9642 no . 3_658
H4 N4 3.2189 no . 2_657
H4 C16 3.3916 no . 3_658
H4 C17 3.0072 no . 3_658
H4 C18 3.4680 no . 3_658
H4 C20 3.0813 no . 2_657
H4 H17 2.9832 no . 3_658
H4 H20 2.4329 no . 2_657
H5 C2 3.4509 no . 4_554
H5 C20 3.2118 no . 2_657
H5 H2 2.7684 no . 4_554
H5 H3 3.1522 no . 4_554
H5 H20 2.7245 no . 2_657
H9A N1 3.4544 no . 3_758
H9A N2 2.9778 no . 3_758
H9A N3 3.3311 no . 3_758
H9A H9B 3.1787 no . 3_758
H9A H12 2.9781 no . 4_545
H9B Br1 3.0364 no . 3_757
H9B F4 2.8684 no . 3_758
H9B N2 3.2944 no . 3_758
H9B N3 3.0369 no . 3_758
H9B C8 3.2998 no . 3_758
H9B C9 3.3899 no . 3_758
H9B H9A 3.1787 no . 3_758
H9B H9B 3.2840 no . 3_758
H11 F4 3.3972 no . 4_544
H11 N2 3.2366 no . 2_747
H11 H1 3.2881 no . 3_758
H12 F1 3.5079 no . 4_544
H12 F4 2.6357 no . 4_544
H12 N1 3.2107 no . 2_747
H12 N2 2.8950 no . 2_747
H12 C14 3.4934 no . 3_757
H12 H9A 2.9781 no . 4_544
H12 H14 3.4837 no . 3_757
H14 Br2 3.5074 no . 4_544
H14 N1 2.8959 no . 4_554
H14 C19 3.3771 no . 4_544
H14 H1 3.4572 no . 1_554
H14 H2 3.2610 no . 1_554
H14 H12 3.4837 no . 3_757
H15 N1 3.5889 no . 4_554
H15 C1 3.1917 no . 4_554
H15 H1 2.7151 no . 4_554
H15 H18 3.5622 no . 4_544
H17 Br1 3.2742 no . 1_556
H17 F1 2.6432 no . 4_545
H17 N4 2.8838 no . 4_545
H17 C20 3.5954 no . 4_545
H17 H4 2.9832 no . 3_658
H17 H20 3.4609 no . 4_545
H18 Br2 3.4443 no . 3_648
H18 S1 3.4619 no . 4_545
H18 F1 2.6539 no . 4_545
H18 F2 2.5278 no . 4_545
H18 N4 3.5373 no . 4_545
H18 C15 3.4364 no . 4_545
H18 H15 3.5622 no . 4_545
H20 F3 3.3339 no . 4_544
H20 C4 3.1232 no . 2_647
H20 C5 3.2633 no . 2_647
H20 H3 3.5064 no . 3_658
H20 H4 2.4329 no . 2_647
H20 H5 2.7245 no . 2_647
H20 H17 3.4609 no . 4_544

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_20171027SF4
_database_code_depnum_ccdc_archive 'CCDC 1823581'
_audit_update_record             
;
2018-02-12 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H14 Br2 F4 N4 S'
_chemical_formula_moiety         'C20 H14 Br2 F4 N4 S'
_chemical_formula_weight         578.22
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.5920(11)
_cell_length_b                   7.7321(7)
_cell_length_c                   21.336(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.291(7)
_cell_angle_gamma                90.0000
_cell_volume                     2064.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7222
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.48
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136.00
_exptl_absorpt_coefficient_mu    4.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.281
_exptl_absorpt_correction_T_max  0.441

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            15318
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4685
_reflns_number_gt                3773
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0772
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4685
_refine_ls_number_parameters     280
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0279P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.680
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br1 Br 0.10218(2) 0.00124(3) 0.075553(13) 0.03955(9) Uani 1.0 4 d . . .
Br2 Br 0.83040(2) 0.84092(3) -0.374428(11) 0.03567(9) Uani 1.0 4 d . . .
S1 S 0.32277(4) 0.60370(6) -0.06995(2) 0.01779(12) Uani 1.0 4 d . . .
F1 F 0.41340(11) 0.61501(15) -0.01083(6) 0.0240(3) Uani 1.0 4 d . . .
F2 F 0.39573(11) 0.46839(14) -0.10491(6) 0.0268(3) Uani 1.0 4 d . . .
F3 F 0.23231(11) 0.59198(15) -0.12989(6) 0.0268(3) Uani 1.0 4 d . . .
F4 F 0.25041(10) 0.73851(14) -0.03642(5) 0.0240(3) Uani 1.0 4 d . . .
N1 N 0.15798(16) 0.4320(3) -0.02856(8) 0.0237(4) Uani 1.0 4 d . . .
N2 N 0.42193(16) 0.9181(3) -0.07160(8) 0.0237(4) Uani 1.0 4 d . . .
N3 N 0.45853(16) 1.0323(2) -0.10975(9) 0.0247(5) Uani 1.0 4 d . . .
N4 N 0.44406(15) 0.9647(2) -0.16868(8) 0.0189(4) Uani 1.0 4 d . . .
C1 C 0.1711(2) 0.1676(3) 0.02918(10) 0.0247(5) Uani 1.0 4 d . . .
C2 C 0.2785(2) 0.1540(3) 0.02360(10) 0.0248(5) Uani 1.0 4 d . . .
C3 C 0.32679(19) 0.2854(3) -0.00775(10) 0.0221(5) Uani 1.0 4 d . . .
C4 C 0.26156(18) 0.4203(3) -0.03175(9) 0.0190(5) Uani 1.0 4 d . . .
C5 C 0.11192(19) 0.3047(3) 0.00153(11) 0.0259(5) Uani 1.0 4 d . . .
C6 C 0.38495(17) 0.7800(3) -0.10666(9) 0.0186(5) Uani 1.0 4 d . . .
C7 C 0.39887(17) 0.8047(3) -0.16894(9) 0.0177(4) Uani 1.0 4 d . . .
C8 C 0.37973(17) 0.7041(3) -0.22827(9) 0.0179(4) Uani 1.0 4 d . . .
C9 C 0.45013(19) 0.5723(3) -0.24004(10) 0.0228(5) Uani 1.0 4 d . . .
C10 C 0.4379(2) 0.4858(3) -0.29709(11) 0.0278(6) Uani 1.0 4 d . . .
C11 C 0.3557(3) 0.5303(3) -0.34291(11) 0.0288(6) Uani 1.0 4 d . . .
C12 C 0.2854(2) 0.6618(3) -0.33147(11) 0.0268(5) Uani 1.0 4 d . . .
C13 C 0.29742(18) 0.7484(3) -0.27372(10) 0.0223(5) Uani 1.0 4 d . . .
C14 C 0.46641(19) 1.0708(3) -0.22252(10) 0.0227(5) Uani 1.0 4 d . . .
C15 C 0.55355(18) 1.0007(3) -0.25826(10) 0.0207(5) Uani 1.0 4 d . . .
C16 C 0.6516(2) 0.9506(3) -0.22779(11) 0.0277(5) Uani 1.0 4 d . . .
C17 C 0.7342(2) 0.8992(3) -0.26122(11) 0.0300(6) Uani 1.0 4 d . . .
C18 C 0.71748(19) 0.8985(3) -0.32654(10) 0.0245(5) Uani 1.0 4 d . . .
C19 C 0.6199(2) 0.9431(3) -0.35798(10) 0.0278(5) Uani 1.0 4 d . . .
C20 C 0.5378(2) 0.9940(3) -0.32355(11) 0.0261(5) Uani 1.0 4 d . . .
H7 H 0.2490 0.8379 -0.2657 0.0268 Uiso 1.0 4 calc R . .
H10A H 0.4868 1.1884 -0.2072 0.0272 Uiso 1.0 4 calc R . .
H10B H 0.4001 1.0814 -0.2518 0.0272 Uiso 1.0 4 calc R . .
H11 H 0.3476 0.4708 -0.3821 0.0346 Uiso 1.0 4 calc R . .
H12 H 0.6623 0.9516 -0.1830 0.0333 Uiso 1.0 4 calc R . .
H13 H 0.3186 0.0576 0.0406 0.0298 Uiso 1.0 4 calc R . .
H14 H 0.0371 0.3083 0.0040 0.0311 Uiso 1.0 4 calc R . .
H16 H 0.4859 0.3955 -0.3049 0.0333 Uiso 1.0 4 calc R . .
H17 H 0.5067 0.5418 -0.2088 0.0273 Uiso 1.0 4 calc R . .
H18 H 0.8010 0.8650 -0.2399 0.0360 Uiso 1.0 4 calc R . .
H19 H 0.4702 1.0245 -0.3449 0.0313 Uiso 1.0 4 calc R . .
H20 H 0.2292 0.6928 -0.3629 0.0322 Uiso 1.0 4 calc R . .
H21 H 0.6089 0.9392 -0.4027 0.0334 Uiso 1.0 4 calc R . .
H22 H 0.4009 0.2830 -0.0125 0.0265 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C1 1.891(3) yes . .
Br2 C18 1.893(3) yes . .
S1 F1 1.6080(14) yes . .
S1 F2 1.6264(14) yes . .
S1 F3 1.6192(14) yes . .
S1 F4 1.6035(13) yes . .
S1 C4 1.846(2) yes . .
S1 C6 1.794(2) yes . .
N1 C4 1.317(3) yes . .
N1 C5 1.342(3) yes . .
N2 N3 1.318(3) yes . .
N2 C6 1.357(3) yes . .
N3 N4 1.355(3) yes . .
N4 C7 1.361(3) yes . .
N4 C14 1.464(3) yes . .
C1 C2 1.374(4) yes . .
C1 C5 1.390(3) yes . .
C2 C3 1.393(4) yes . .
C3 C4 1.390(3) yes . .
C6 C7 1.373(3) yes . .
C7 C8 1.483(3) yes . .
C8 C9 1.391(3) yes . .
C8 C13 1.383(3) yes . .
C9 C10 1.383(3) yes . .
C10 C11 1.387(4) yes . .
C11 C12 1.388(4) yes . .
C12 C13 1.396(3) yes . .
C14 C15 1.504(4) yes . .
C15 C16 1.387(4) yes . .
C15 C20 1.386(4) yes . .
C16 C17 1.382(4) yes . .
C17 C18 1.386(4) yes . .
C18 C19 1.378(4) yes . .
C19 C20 1.390(4) yes . .
C2 H13 0.950 no . .
C3 H22 0.950 no . .
C5 H14 0.950 no . .
C9 H17 0.950 no . .
C10 H16 0.950 no . .
C11 H11 0.950 no . .
C12 H20 0.950 no . .
C13 H7 0.950 no . .
C14 H10A 0.990 no . .
C14 H10B 0.990 no . .
C16 H12 0.950 no . .
C17 H18 0.950 no . .
C19 H21 0.950 no . .
C20 H19 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
F1 S1 F2 90.39(7) yes . . .
F1 S1 F3 179.50(8) yes . . .
F1 S1 F4 90.22(7) yes . . .
F1 S1 C4 89.44(8) yes . . .
F1 S1 C6 89.71(8) yes . . .
F2 S1 F3 89.18(7) yes . . .
F2 S1 F4 179.18(7) yes . . .
F2 S1 C4 89.57(9) yes . . .
F2 S1 C6 89.60(9) yes . . .
F3 S1 F4 90.22(7) yes . . .
F3 S1 C4 90.81(8) yes . . .
F3 S1 C6 90.03(8) yes . . .
F4 S1 C4 90.99(9) yes . . .
F4 S1 C6 89.85(9) yes . . .
C4 S1 C6 178.81(10) yes . . .
C4 N1 C5 117.18(19) yes . . .
N3 N2 C6 108.01(17) yes . . .
N2 N3 N4 107.08(16) yes . . .
N3 N4 C7 111.59(17) yes . . .
N3 N4 C14 119.58(16) yes . . .
C7 N4 C14 128.49(17) yes . . .
Br1 C1 C2 120.39(16) yes . . .
Br1 C1 C5 119.04(19) yes . . .
C2 C1 C5 120.6(2) yes . . .
C1 C2 C3 118.1(2) yes . . .
C2 C3 C4 116.9(3) yes . . .
S1 C4 N1 115.71(15) yes . . .
S1 C4 C3 118.72(18) yes . . .
N1 C4 C3 125.5(2) yes . . .
N1 C5 C1 121.6(3) yes . . .
S1 C6 N2 119.81(15) yes . . .
S1 C6 C7 129.55(15) yes . . .
N2 C6 C7 110.58(18) yes . . .
N4 C7 C6 102.73(17) yes . . .
N4 C7 C8 120.60(18) yes . . .
C6 C7 C8 136.65(18) yes . . .
C7 C8 C9 119.42(18) yes . . .
C7 C8 C13 120.50(18) yes . . .
C9 C8 C13 119.91(19) yes . . .
C8 C9 C10 120.1(2) yes . . .
C9 C10 C11 120.2(3) yes . . .
C10 C11 C12 120.0(2) yes . . .
C11 C12 C13 119.8(2) yes . . .
C8 C13 C12 120.0(2) yes . . .
N4 C14 C15 114.16(17) yes . . .
C14 C15 C16 121.7(2) yes . . .
C14 C15 C20 119.4(2) yes . . .
C16 C15 C20 118.9(3) yes . . .
C15 C16 C17 121.3(3) yes . . .
C16 C17 C18 118.7(3) yes . . .
Br2 C18 C17 120.23(18) yes . . .
Br2 C18 C19 118.60(17) yes . . .
C17 C18 C19 121.2(3) yes . . .
C18 C19 C20 119.3(2) yes . . .
C15 C20 C19 120.6(3) yes . . .
C1 C2 H13 120.934 no . . .
C3 C2 H13 120.939 no . . .
C2 C3 H22 121.531 no . . .
C4 C3 H22 121.537 no . . .
N1 C5 H14 119.223 no . . .
C1 C5 H14 119.225 no . . .
C8 C9 H17 119.951 no . . .
C10 C9 H17 119.938 no . . .
C9 C10 H16 119.901 no . . .
C11 C10 H16 119.925 no . . .
C10 C11 H11 120.026 no . . .
C12 C11 H11 120.014 no . . .
C11 C12 H20 120.091 no . . .
C13 C12 H20 120.092 no . . .
C8 C13 H7 119.990 no . . .
C12 C13 H7 119.982 no . . .
N4 C14 H10A 108.709 no . . .
N4 C14 H10B 108.724 no . . .
C15 C14 H10A 108.722 no . . .
C15 C14 H10B 108.712 no . . .
H10A C14 H10B 107.627 no . . .
C15 C16 H12 119.331 no . . .
C17 C16 H12 119.331 no . . .
C16 C17 H18 120.635 no . . .
C18 C17 H18 120.657 no . . .
C18 C19 H21 120.357 no . . .
C20 C19 H21 120.347 no . . .
C15 C20 H19 119.705 no . . .
C19 C20 H19 119.724 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
F1 S1 C4 N1 130.23(13) no . . . .
F1 S1 C4 C3 -48.30(14) no . . . .
F1 S1 C6 N2 -42.07(15) no . . . .
F1 S1 C6 C7 141.10(18) no . . . .
F2 S1 C4 N1 -139.38(13) no . . . .
F2 S1 C4 C3 42.09(14) no . . . .
F2 S1 C6 N2 -132.46(15) no . . . .
F2 S1 C6 C7 50.71(18) no . . . .
F3 S1 C4 N1 -50.21(14) no . . . .
F3 S1 C4 C3 131.26(13) no . . . .
F3 S1 C6 N2 138.36(15) no . . . .
F3 S1 C6 C7 -38.47(18) no . . . .
F4 S1 C4 N1 40.02(13) no . . . .
F4 S1 C4 C3 -138.51(13) no . . . .
F4 S1 C6 N2 48.15(15) no . . . .
F4 S1 C6 C7 -128.68(18) no . . . .
C4 N1 C5 C1 1.1(3) no . . . .
C5 N1 C4 S1 -176.99(15) no . . . .
C5 N1 C4 C3 1.4(3) no . . . .
N3 N2 C6 S1 -176.81(15) no . . . .
N3 N2 C6 C7 0.6(3) no . . . .
C6 N2 N3 N4 0.0(3) no . . . .
N2 N3 N4 C7 -0.7(3) no . . . .
N2 N3 N4 C14 173.25(16) no . . . .
N3 N4 C7 C6 1.0(3) no . . . .
N3 N4 C7 C8 -177.65(16) no . . . .
N3 N4 C14 C15 118.27(19) no . . . .
C7 N4 C14 C15 -68.9(3) no . . . .
C14 N4 C7 C6 -172.27(19) no . . . .
C14 N4 C7 C8 9.1(4) no . . . .
Br1 C1 C2 C3 -176.13(12) no . . . .
Br1 C1 C5 N1 175.82(14) no . . . .
C2 C1 C5 N1 -3.4(4) no . . . .
C5 C1 C2 C3 3.1(3) no . . . .
C1 C2 C3 C4 -0.7(3) no . . . .
C2 C3 C4 S1 176.74(15) no . . . .
C2 C3 C4 N1 -1.6(3) no . . . .
S1 C6 C7 N4 176.13(15) no . . . .
S1 C6 C7 C8 -5.6(4) no . . . .
N2 C6 C7 N4 -0.9(3) no . . . .
N2 C6 C7 C8 177.3(2) no . . . .
N4 C7 C8 C9 100.9(2) no . . . .
N4 C7 C8 C13 -74.3(3) no . . . .
C6 C7 C8 C9 -77.2(4) no . . . .
C6 C7 C8 C13 107.6(3) no . . . .
C7 C8 C9 C10 -175.27(17) no . . . .
C7 C8 C13 C12 174.84(17) no . . . .
C9 C8 C13 C12 -0.4(3) no . . . .
C13 C8 C9 C10 0.0(3) no . . . .
C8 C9 C10 C11 0.3(4) no . . . .
C9 C10 C11 C12 -0.1(4) no . . . .
C10 C11 C12 C13 -0.2(4) no . . . .
C11 C12 C13 C8 0.5(4) no . . . .
N4 C14 C15 C16 -49.8(3) no . . . .
N4 C14 C15 C20 133.57(17) no . . . .
C14 C15 C16 C17 -174.81(17) no . . . .
C14 C15 C20 C19 174.73(16) no . . . .
C16 C15 C20 C19 -2.0(3) no . . . .
C20 C15 C16 C17 1.9(3) no . . . .
C15 C16 C17 C18 0.1(4) no . . . .
C16 C17 C18 Br2 176.67(18) no . . . .
C16 C17 C18 C19 -1.9(4) no . . . .
Br2 C18 C19 C20 -176.85(13) no . . . .
C17 C18 C19 C20 1.7(4) no . . . .
C18 C19 C20 C15 0.3(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 N1 3.496(3) no . .
F1 N2 2.686(3) no . .
F1 C3 2.776(3) no . .
F2 N1 3.573(3) no . .
F2 N2 3.557(2) no . .
F2 C3 2.729(3) no . .
F2 C7 2.940(3) no . .
F2 C8 3.189(3) no . .
F2 C9 3.140(3) no . .
F3 N1 2.743(3) no . .
F3 N2 3.599(3) no . .
F3 C7 2.860(3) no . .
F3 C8 3.075(3) no . .
F3 C13 3.479(3) no . .
F4 N1 2.653(3) no . .
F4 N2 2.741(3) no . .
F4 C7 3.593(3) no . .
N1 C2 2.792(3) no . .
N2 C14 3.532(3) no . .
N3 C15 3.516(3) no . .
N4 C9 3.399(3) no . .
N4 C13 3.213(3) no . .
N4 C16 3.026(4) no . .
C1 C4 2.670(3) no . .
C3 C5 2.738(4) no . .
C6 C9 3.444(3) no . .
C6 C14 3.574(3) no . .
C7 C15 3.246(3) no . .
C8 C11 2.778(3) no . .
C8 C14 3.036(3) no . .
C8 C15 3.281(3) no . .
C9 C12 2.775(4) no . .
C9 C15 3.596(3) no . .
C10 C13 2.774(4) no . .
C13 C14 3.380(3) no . .
C15 C18 2.769(4) no . .
C16 C19 2.763(4) no . .
C17 C20 2.775(4) no . .
Br1 C10 3.592(3) no . 4_455
Br2 F1 3.2163(15) no . 4_564
Br2 F4 3.5460(12) no . 4_564
F1 Br2 3.2163(15) no . 4_465
F1 F1 2.8129(19) no . 3_665
F1 F2 3.3150(18) no . 3_665
F1 C3 3.342(3) no . 3_665
F2 F1 3.3150(18) no . 3_665
F2 N3 3.467(2) no . 1_545
F2 C12 3.462(3) no . 2_544
F3 C11 3.593(3) no . 2_554
F3 C12 3.428(3) no . 2_544
F3 C13 3.355(3) no . 2_544
F3 C20 3.519(3) no . 2_544
F4 Br2 3.5460(12) no . 4_465
F4 C2 3.462(3) no . 1_565
F4 C11 3.571(3) no . 2_554
N2 C2 3.394(3) no . 1_565
N2 C3 3.423(3) no . 1_565
N3 F2 3.467(2) no . 1_565
N3 C3 3.480(3) no . 1_565
N3 C12 3.341(3) no . 2_554
N4 C12 3.267(3) no . 2_554
C2 F4 3.462(3) no . 1_545
C2 N2 3.394(3) no . 1_545
C3 F1 3.342(3) no . 3_665
C3 N2 3.423(3) no . 1_545
C3 N3 3.480(3) no . 1_545
C4 C12 3.533(3) no . 2_544
C5 C19 3.568(4) no . 4_465
C10 Br1 3.592(3) no . 4_554
C10 C14 3.582(3) no . 1_545
C11 F3 3.593(3) no . 2_544
C11 F4 3.571(3) no . 2_544
C12 F2 3.462(3) no . 2_554
C12 F3 3.428(3) no . 2_554
C12 N3 3.341(3) no . 2_544
C12 N4 3.267(3) no . 2_544
C12 C4 3.533(3) no . 2_554
C12 C14 3.560(4) no . 2_544
C13 F3 3.355(3) no . 2_554
C13 C14 3.588(4) no . 2_544
C14 C10 3.582(3) no . 1_565
C14 C12 3.560(4) no . 2_554
C14 C13 3.588(4) no . 2_554
C19 C5 3.568(4) no . 4_564
C20 F3 3.519(3) no . 2_554
Br1 H13 2.9357 no . .
Br1 H14 2.8924 no . .
Br2 H18 2.9406 no . .
Br2 H21 2.8899 no . .
S1 H22 2.8902 no . .
F1 H22 2.5717 no . .
F2 H17 2.8054 no . .
F2 H22 2.4324 no . .
F3 H7 3.4907 no . .
N1 H22 3.2514 no . .
N3 H10A 2.4632 no . .
N3 H10B 3.0638 no . .
N3 H12 3.2090 no . .
N4 H7 3.1870 no . .
N4 H12 2.8003 no . .
N4 H17 3.4924 no . .
C1 H22 3.2442 no . .
C2 H14 3.2497 no . .
C4 H13 3.2439 no . .
C4 H14 3.1295 no . .
C5 H13 3.2625 no . .
C6 H17 3.3507 no . .
C7 H7 2.6513 no . .
C7 H10A 3.3000 no . .
C7 H10B 2.7772 no . .
C7 H12 3.5500 no . .
C7 H17 2.6372 no . .
C8 H10B 2.9768 no . .
C8 H16 3.2609 no . .
C8 H20 3.2638 no . .
C9 H7 3.2596 no . .
C9 H11 3.2579 no . .
C10 H20 3.2605 no . .
C11 H7 3.2657 no . .
C11 H17 3.2578 no . .
C12 H16 3.2596 no . .
C13 H10B 2.8961 no . .
C13 H11 3.2673 no . .
C13 H17 3.2580 no . .
C13 H19 3.5101 no . .
C14 H7 3.3209 no . .
C14 H12 2.6816 no . .
C14 H19 2.6417 no . .
C15 H18 3.2707 no . .
C15 H21 3.2684 no . .
C16 H10A 2.8428 no . .
C16 H10B 3.3108 no . .
C16 H19 3.2468 no . .
C17 H21 3.2640 no . .
C18 H12 3.2393 no . .
C18 H19 3.2451 no . .
C19 H18 3.2646 no . .
C20 H10A 3.0300 no . .
C20 H10B 2.5263 no . .
C20 H12 3.2445 no . .
H7 H10B 2.6698 no . .
H7 H20 2.3471 no . .
H10A H12 2.8728 no . .
H10A H19 3.1858 no . .
H10B H19 2.3024 no . .
H11 H16 2.3365 no . .
H11 H20 2.3391 no . .
H12 H18 2.3309 no . .
H13 H22 2.3778 no . .
H16 H17 2.3305 no . .
H19 H21 2.3405 no . .
Br1 H11 3.4317 no . 4_455
Br1 H12 3.5629 no . 3_665
Br1 H14 3.3213 no . 3_555
Br1 H16 3.1784 no . 4_455
Br1 H21 3.4365 no . 4_455
Br2 H10A 2.9739 no . 2_644
Br2 H12 3.2481 no . 2_644
Br2 H13 3.5698 no . 4_554
Br2 H17 2.9962 no . 2_654
S1 H20 3.5173 no . 2_544
F1 H22 2.4662 no . 3_665
F2 H7 3.2961 no . 2_544
F2 H10A 3.3638 no . 1_545
F2 H20 2.6927 no . 2_544
F3 H7 2.9991 no . 2_544
F3 H10B 2.8693 no . 2_544
F3 H11 3.1166 no . 2_554
F3 H19 2.6005 no . 2_544
F3 H20 3.1307 no . 2_544
F4 H11 2.7017 no . 2_554
F4 H13 3.0364 no . 1_565
N1 H14 3.2590 no . 3_565
N1 H19 3.0735 no . 2_544
N1 H20 3.3955 no . 2_544
N1 H21 3.5166 no . 2_544
N1 H21 2.9909 no . 4_465
N2 H11 3.4529 no . 2_554
N2 H13 3.0453 no . 1_565
N2 H13 3.2667 no . 3_665
N2 H20 3.0833 no . 2_554
N2 H22 3.1138 no . 1_565
N2 H22 3.1205 no . 3_665
N3 H13 3.1024 no . 3_665
N3 H20 2.6770 no . 2_554
N3 H22 2.9865 no . 1_565
N4 H20 2.9402 no . 2_554
C1 H11 3.4719 no . 2_544
C1 H21 3.4958 no . 4_465
C2 H11 3.5480 no . 2_544
C2 H12 3.4978 no . 3_665
C2 H20 3.4336 no . 2_544
C3 H20 2.8645 no . 2_544
C4 H20 2.8674 no . 2_544
C5 H14 3.5272 no . 3_565
C5 H21 3.4602 no . 2_544
C5 H21 2.8486 no . 4_465
C6 H11 3.2639 no . 2_554
C6 H20 3.5319 no . 2_554
C6 H22 3.5314 no . 3_665
C7 H20 3.5078 no . 2_554
C8 H7 3.2579 no . 2_544
C9 H7 3.1074 no . 2_544
C9 H10A 3.0737 no . 1_545
C9 H18 3.5871 no . 2_644
C10 H7 3.0546 no . 2_544
C10 H10A 3.0144 no . 1_545
C10 H10B 3.3214 no . 1_545
C10 H18 3.4253 no . 2_644
C11 H7 3.1601 no . 2_544
C12 H7 3.3089 no . 2_544
C12 H10B 3.1483 no . 2_544
C13 H7 3.3511 no . 2_544
C13 H10A 3.5877 no . 2_544
C13 H10B 2.9069 no . 2_544
C14 H7 3.3971 no . 2_554
C14 H16 3.0900 no . 1_565
C14 H20 3.3551 no . 2_554
C15 H16 3.2939 no . 1_565
C15 H18 3.3623 no . 2_654
C16 H18 3.3452 no . 2_654
C17 H17 3.5677 no . 2_654
C19 H14 3.5751 no . 4_564
C20 H16 3.2061 no . 1_565
H7 F2 3.2961 no . 2_554
H7 F3 2.9991 no . 2_554
H7 C8 3.2579 no . 2_554
H7 C9 3.1074 no . 2_554
H7 C10 3.0546 no . 2_554
H7 C11 3.1601 no . 2_554
H7 C12 3.3089 no . 2_554
H7 C13 3.3511 no . 2_554
H7 C14 3.3971 no . 2_544
H7 H10A 3.1807 no . 2_544
H7 H10B 2.7848 no . 2_544
H7 H16 3.4923 no . 2_554
H7 H17 3.5731 no . 2_554
H10A Br2 2.9739 no . 2_654
H10A F2 3.3638 no . 1_565
H10A C9 3.0737 no . 1_565
H10A C10 3.0144 no . 1_565
H10A C13 3.5877 no . 2_554
H10A H7 3.1807 no . 2_554
H10A H16 2.6281 no . 1_565
H10A H17 2.7448 no . 1_565
H10A H18 3.3076 no . 2_654
H10A H20 3.2440 no . 2_554
H10B F3 2.8693 no . 2_554
H10B C10 3.3214 no . 1_565
H10B C12 3.1483 no . 2_554
H10B C13 2.9069 no . 2_554
H10B H7 2.7848 no . 2_554
H10B H16 2.9352 no . 1_565
H10B H20 3.2022 no . 2_554
H11 Br1 3.4317 no . 4_554
H11 F3 3.1166 no . 2_544
H11 F4 2.7017 no . 2_544
H11 N2 3.4529 no . 2_544
H11 C1 3.4719 no . 2_554
H11 C2 3.5480 no . 2_554
H11 C6 3.2639 no . 2_544
H12 Br1 3.5629 no . 3_665
H12 Br2 3.2481 no . 2_654
H12 C2 3.4978 no . 3_665
H12 H13 3.0217 no . 3_665
H13 Br2 3.5698 no . 4_455
H13 F4 3.0364 no . 1_545
H13 N2 3.0453 no . 1_545
H13 N2 3.2667 no . 3_665
H13 N3 3.1024 no . 3_665
H13 H12 3.0217 no . 3_665
H14 Br1 3.3213 no . 3_555
H14 N1 3.2590 no . 3_565
H14 C5 3.5272 no . 3_565
H14 C19 3.5751 no . 4_465
H14 H14 3.1071 no . 3_565
H14 H21 2.8637 no . 2_544
H14 H21 2.8632 no . 4_465
H16 Br1 3.1784 no . 4_554
H16 C14 3.0900 no . 1_545
H16 C15 3.2939 no . 1_545
H16 C20 3.2061 no . 1_545
H16 H7 3.4923 no . 2_544
H16 H10A 2.6281 no . 1_545
H16 H10B 2.9352 no . 1_545
H16 H18 2.7573 no . 2_644
H16 H19 2.9937 no . 1_545
H17 Br2 2.9962 no . 2_644
H17 C17 3.5677 no . 2_644
H17 H7 3.5731 no . 2_544
H17 H10A 2.7448 no . 1_545
H17 H18 3.0838 no . 2_644
H18 C9 3.5871 no . 2_654
H18 C10 3.4253 no . 2_654
H18 C15 3.3623 no . 2_644
H18 C16 3.3452 no . 2_644
H18 H10A 3.3076 no . 2_644
H18 H16 2.7573 no . 2_654
H18 H17 3.0838 no . 2_654
H19 F3 2.6005 no . 2_554
H19 N1 3.0735 no . 2_554
H19 H16 2.9937 no . 1_565
H20 S1 3.5173 no . 2_554
H20 F2 2.6927 no . 2_554
H20 F3 3.1307 no . 2_554
H20 N1 3.3955 no . 2_554
H20 N2 3.0833 no . 2_544
H20 N3 2.6770 no . 2_544
H20 N4 2.9402 no . 2_544
H20 C2 3.4336 no . 2_554
H20 C3 2.8645 no . 2_554
H20 C4 2.8674 no . 2_554
H20 C6 3.5319 no . 2_544
H20 C7 3.5078 no . 2_544
H20 C14 3.3551 no . 2_544
H20 H10A 3.2440 no . 2_544
H20 H10B 3.2022 no . 2_544
H20 H22 3.0475 no . 2_554
H21 Br1 3.4365 no . 4_554
H21 N1 3.5166 no . 2_554
H21 N1 2.9909 no . 4_564
H21 C1 3.4958 no . 4_564
H21 C5 3.4602 no . 2_554
H21 C5 2.8486 no . 4_564
H21 H14 2.8637 no . 2_554
H21 H14 2.8632 no . 4_564
H22 F1 2.4662 no . 3_665
H22 N2 3.1138 no . 1_545
H22 N2 3.1205 no . 3_665
H22 N3 2.9865 no . 1_545
H22 C6 3.5314 no . 3_665
H22 H20 3.0475 no . 2_544

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
