# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_IIR610
_database_code_depnum_ccdc_archive 'CCDC 1564784'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
'4-(Naphthalen-2-yl)benzo[c][1,2,5]thiadiazole '
_chemical_formula_moiety         'C16 H10 N2 S'
_chemical_formula_sum            'C16 H10 N2 S'
_chemical_formula_weight         262.32
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
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                   48.765(5)
_cell_length_b                   7.4625(8)
_cell_length_c                   7.0053(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.573(4)
_cell_angle_gamma                90
_cell_volume                     2532.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7759
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.50
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.510
_exptl_crystal_size_min          0.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1088
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.436
_exptl_absorpt_correction_T_max  0.967

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_r_equivalents  0.0719
_diffrn_reflns_av_uneti/neti     0.0598
_diffrn_reflns_number            15916
_diffrn_reflns_limit_h_min       -62
_diffrn_reflns_limit_h_max       62
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.007
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             2908
_reflns_number_gt                2425
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_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     
'w=1/[σ²(Fo²)+(0.1382P)²+1.2287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2908
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2022
_refine_ls_wR_factor_gt          0.1899
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.596
_refine_diff_density_min         -1.090
_refine_diff_density_rms         0.206

#...............................................................................
# .RES SHELXL file: IIR610.res
# .HKL SHELXL file: IIR610.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.68129(4) 0.3464(3) 0.7360(3) 0.0152(4) Uani 1 1 d . . . . .
C2 C 0.70564(4) 0.4518(3) 0.7884(3) 0.0186(5) Uani 1 1 d . . . . .
C3 C 0.70488(5) 0.6409(3) 0.7791(3) 0.0216(5) Uani 1 1 d . . . . .
H3 H 0.720920 0.711062 0.814302 0.026 Uiso 1 1 calc R U . . .
C4 C 0.67993(5) 0.7188(3) 0.7169(3) 0.0205(5) Uani 1 1 d . . . . .
H4 H 0.678731 0.845752 0.709501 0.025 Uiso 1 1 calc R U . . .
C5 C 0.65586(4) 0.6149(3) 0.6632(3) 0.0182(4) Uani 1 1 d . . . . .
H5 H 0.639246 0.675460 0.617890 0.022 Uiso 1 1 calc R U . . .
C6 C 0.65543(4) 0.4305(3) 0.6736(3) 0.0156(4) Uani 1 1 d . . . . .
C7 C 0.62950(4) 0.3300(3) 0.6211(3) 0.0164(4) Uani 1 1 d . . . . .
C8 C 0.62908(5) 0.1635(3) 0.5205(3) 0.0194(5) Uani 1 1 d . . . . .
H8 H 0.645990 0.109103 0.497127 0.023 Uiso 1 1 calc R U . . .
C9 C 0.60460(5) 0.0812(3) 0.4573(3) 0.0259(5) Uani 1 1 d . . . . .
H9 H 0.604718 -0.028784 0.389160 0.031 Uiso 1 1 calc R U . . .
C10 C 0.57903(5) 0.1585(3) 0.4925(3) 0.0274(6) Uani 1 1 d . . . . .
C11 C 0.55331(6) 0.0797(4) 0.4234(4) 0.0396(7) Uani 1 1 d . . . . .
H11 H 0.552880 -0.028280 0.351314 0.048 Uiso 1 1 calc R U . . .
C12 C 0.52916(6) 0.1584(5) 0.4599(4) 0.0475(9) Uani 1 1 d . . . . .
H12 H 0.512074 0.105263 0.411201 0.057 Uiso 1 1 calc R U . . .
C13 C 0.52922(6) 0.3157(5) 0.5677(4) 0.0461(8) Uani 1 1 d . . . . .
H13 H 0.512202 0.367053 0.593482 0.055 Uiso 1 1 calc R U . . .
C14 C 0.55368(5) 0.3971(4) 0.6370(4) 0.0356(6) Uani 1 1 d . . . . .
H14 H 0.553523 0.504192 0.710299 0.043 Uiso 1 1 calc R U . . .
C15 C 0.57922(5) 0.3205(3) 0.5986(3) 0.0253(5) Uani 1 1 d . . . . .
C16 C 0.60478(4) 0.4030(3) 0.6618(3) 0.0204(5) Uani 1 1 d . . . . .
H16 H 0.604951 0.511005 0.733757 0.024 Uiso 1 1 calc R U . . .
N1 N 0.68595(4) 0.1688(2) 0.7582(3) 0.0198(4) Uani 1 1 d . . . . .
N2 N 0.72813(4) 0.3519(2) 0.8467(3) 0.0251(5) Uani 1 1 d . . . . .
S1 S 0.71813(2) 0.14556(7) 0.83514(9) 0.0271(3) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
C1 N1 1.350(3) . ?
C1 C6 1.431(3) . ?
C1 C2 1.437(3) . ?
C2 N2 1.350(3) . ?
C2 C3 1.413(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.421(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.480(3) . ?
C7 C16 1.382(3) . ?
C7 C8 1.427(3) . ?
C8 C9 1.371(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.420(4) . ?
C9 H9 0.9500 . ?
C10 C15 1.419(4) . ?
C10 C11 1.420(3) . ?
C11 C12 1.366(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.424(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.415(3) . ?
C16 H16 0.9500 . ?
N1 S1 1.609(2) . ?
N2 S1 1.6141(19) . ?

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
N1 C1 C6 126.58(18) . . ?
N1 C1 C2 112.63(19) . . ?
C6 C1 C2 120.77(18) . . ?
N2 C2 C3 125.6(2) . . ?
N2 C2 C1 113.2(2) . . ?
C3 C2 C1 121.23(19) . . ?
C4 C3 C2 117.07(19) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 121.8(2) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 123.2(2) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C6 C1 115.83(18) . . ?
C5 C6 C7 120.67(19) . . ?
C1 C6 C7 123.50(18) . . ?
C16 C7 C8 118.8(2) . . ?
C16 C7 C6 119.33(19) . . ?
C8 C7 C6 121.81(19) . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C15 C10 C11 118.9(3) . . ?
C15 C10 C9 118.9(2) . . ?
C11 C10 C9 122.1(3) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C10 119.2(2) . . ?
C16 C15 C14 121.6(2) . . ?
C10 C15 C14 119.2(2) . . ?
C7 C16 C15 121.5(2) . . ?
C7 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C1 N1 S1 106.80(14) . . ?
C2 N2 S1 106.35(16) . . ?
N1 S1 N2 101.03(10) . . ?

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
N1 C1 C2 N2 0.7(3) . . . . ?
C6 C1 C2 N2 179.03(19) . . . . ?
N1 C1 C2 C3 -178.7(2) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
N2 C2 C3 C4 -179.6(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
C4 C5 C6 C7 178.15(18) . . . . ?
N1 C1 C6 C5 179.6(2) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
N1 C1 C6 C7 -0.8(3) . . . . ?
C2 C1 C6 C7 -178.81(18) . . . . ?
C5 C6 C7 C16 -35.1(3) . . . . ?
C1 C6 C7 C16 145.4(2) . . . . ?
C5 C6 C7 C8 141.7(2) . . . . ?
C1 C6 C7 C8 -37.9(3) . . . . ?
C16 C7 C8 C9 3.0(3) . . . . ?
C6 C7 C8 C9 -173.76(19) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C15 -1.6(3) . . . . ?
C8 C9 C10 C11 177.8(2) . . . . ?
C15 C10 C11 C12 -0.4(4) . . . . ?
C9 C10 C11 C12 -179.9(2) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 1.2(4) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C11 C10 C15 C16 -177.7(2) . . . . ?
C9 C10 C15 C16 1.7(3) . . . . ?
C11 C10 C15 C14 1.6(3) . . . . ?
C9 C10 C15 C14 -179.0(2) . . . . ?
C13 C14 C15 C16 177.9(2) . . . . ?
C13 C14 C15 C10 -1.4(4) . . . . ?
C8 C7 C16 C15 -2.8(3) . . . . ?
C6 C7 C16 C15 174.01(19) . . . . ?
C10 C15 C16 C7 0.5(3) . . . . ?
C14 C15 C16 C7 -178.8(2) . . . . ?
C6 C1 N1 S1 -178.80(17) . . . . ?
C2 C1 N1 S1 -0.6(2) . . . . ?
C3 C2 N2 S1 178.89(19) . . . . ?
C1 C2 N2 S1 -0.5(2) . . . . ?
C1 N1 S1 N2 0.31(18) . . . . ?
C2 N2 S1 N1 0.09(18) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR IIR610                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: cyclohexane'
####################################################################### 
# 
# 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_IIP665
_database_code_depnum_ccdc_archive 'CCDC 1577123'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H12 N2 S'
_chemical_formula_sum            'C22 H12 N2 S'
_chemical_formula_weight         336.40
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4312(8)
_cell_length_b                   9.1773(9)
_cell_length_c                   10.6084(11)
_cell_angle_alpha                83.752(4)
_cell_angle_beta                 69.103(3)
_cell_angle_gamma                87.077(3)
_cell_volume                     762.22(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             348
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.970

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0376
_diffrn_reflns_av_uneti/neti     0.0312
_diffrn_reflns_number            17768
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.186
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3480
_reflns_number_gt                3037
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_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     
'w=1/[σ²(Fo²)+(0.0437P)²+0.4151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3480
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.056

#...............................................................................
# .RES SHELXL file: IIP665.res
# .HKL SHELXL file: IIP665.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.49040(17) 0.63630(14) 0.13768(13) 0.0160(3) Uani 1 1 d . . . . .
C2 C 0.34692(17) 0.54255(14) 0.18135(13) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.32247(17) 0.43371(14) 0.29280(13) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.44838(18) 0.41890(15) 0.35576(14) 0.0183(3) Uani 1 1 d . . . . .
H4 H 0.435552 0.345124 0.428700 0.022 Uiso 1 1 calc R U . . .
C5 C 0.58501(18) 0.50746(15) 0.31381(14) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.666091 0.494098 0.357511 0.024 Uiso 1 1 calc R U . . .
C6 C 0.60952(17) 0.62100(15) 0.20466(14) 0.0178(3) Uani 1 1 d . . . . .
C7 C 0.74453(18) 0.71942(16) 0.16485(16) 0.0228(3) Uani 1 1 d . . . . .
H7 H 0.824198 0.710853 0.209990 0.027 Uiso 1 1 calc R U . . .
C8 C 0.76252(19) 0.82911(17) 0.06008(17) 0.0268(3) Uani 1 1 d . . . . .
H8 H 0.853395 0.896037 0.035233 0.032 Uiso 1 1 calc R U . . .
C9 C 0.64956(19) 0.84234(16) -0.00885(16) 0.0248(3) Uani 1 1 d . . . . .
H9 H 0.665636 0.916519 -0.081930 0.030 Uiso 1 1 calc R U . . .
C10 C 0.51210(18) 0.74750(14) 0.02815(14) 0.0184(3) Uani 1 1 d . . . . .
C11 C 0.39123(19) 0.75931(15) -0.03979(14) 0.0206(3) Uani 1 1 d . . . . .
H11 H 0.407133 0.830495 -0.115137 0.025 Uiso 1 1 calc R U . . .
C12 C 0.25536(18) 0.67073(15) 0.00189(14) 0.0193(3) Uani 1 1 d . . . . .
H12 H 0.177123 0.681220 -0.044571 0.023 Uiso 1 1 calc R U . . .
C13 C 0.22645(17) 0.56103(14) 0.11484(13) 0.0158(3) Uani 1 1 d . . . . .
C14 C 0.08130(18) 0.47448(15) 0.16460(14) 0.0186(3) Uani 1 1 d . . . . .
H14 H 0.000041 0.485466 0.120988 0.022 Uiso 1 1 calc R U . . .
C15 C 0.05425(18) 0.37294(14) 0.27657(15) 0.0186(3) Uani 1 1 d . . . . .
H15 H -0.047510 0.318178 0.310532 0.022 Uiso 1 1 calc R U . . .
C16 C 0.17333(17) 0.34940(14) 0.34052(13) 0.0160(3) Uani 1 1 d . . . . .
C17 C 0.13400(17) 0.23880(14) 0.46062(14) 0.0160(3) Uani 1 1 d . . . . .
C18 C -0.00384(18) 0.25543(15) 0.57611(14) 0.0192(3) Uani 1 1 d . . . . .
H18 H -0.070151 0.342884 0.580632 0.023 Uiso 1 1 calc R U . . .
C19 C -0.05196(18) 0.14733(16) 0.68961(14) 0.0210(3) Uani 1 1 d . . . . .
H19 H -0.148701 0.165027 0.766919 0.025 Uiso 1 1 calc R U . . .
C20 C 0.03696(19) 0.01943(15) 0.69021(14) 0.0211(3) Uani 1 1 d . . . . .
H20 H 0.004398 -0.051688 0.766599 0.025 Uiso 1 1 calc R U . . .
C21 C 0.17982(17) -0.00398(14) 0.57289(14) 0.0181(3) Uani 1 1 d . . . . .
C22 C 0.22839(17) 0.10465(14) 0.45845(14) 0.0162(3) Uani 1 1 d . . . . .
N1 N 0.27906(16) -0.12547(13) 0.55337(13) 0.0236(3) Uani 1 1 d . . . . .
N2 N 0.36331(15) 0.06366(13) 0.35396(13) 0.0211(3) Uani 1 1 d . . . . .
S1 S 0.41735(5) -0.09834(4) 0.40224(4) 0.02562(12) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
C1 C6 1.4164(19) . ?
C1 C10 1.4263(19) . ?
C1 C2 1.4275(18) . ?
C2 C13 1.4233(19) . ?
C2 C3 1.4241(18) . ?
C3 C16 1.4128(18) . ?
C3 C4 1.4363(19) . ?
C4 C5 1.355(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.435(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.4031(19) . ?
C7 C8 1.387(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.437(2) . ?
C11 C12 1.351(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.4362(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3979(19) . ?
C14 C15 1.3853(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3953(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.4882(18) . ?
C17 C18 1.3717(19) . ?
C17 C22 1.4293(18) . ?
C18 C19 1.425(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.361(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.417(2) . ?
C20 H20 0.9500 . ?
C21 N1 1.3482(18) . ?
C21 C22 1.4349(19) . ?
C22 N2 1.3460(18) . ?
N1 S1 1.6127(14) . ?
N2 S1 1.6162(13) . ?

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
C6 C1 C10 119.91(12) . . ?
C6 C1 C2 120.12(12) . . ?
C10 C1 C2 119.96(12) . . ?
C13 C2 C3 120.28(12) . . ?
C13 C2 C1 119.52(12) . . ?
C3 C2 C1 120.18(12) . . ?
C16 C3 C2 119.18(12) . . ?
C16 C3 C4 122.70(12) . . ?
C2 C3 C4 118.07(12) . . ?
C5 C4 C3 121.70(13) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 121.25(13) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C1 119.15(13) . . ?
C7 C6 C5 122.19(13) . . ?
C1 C6 C5 118.64(12) . . ?
C8 C7 C6 120.48(14) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.84(14) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.67(14) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C1 118.91(13) . . ?
C9 C10 C11 122.17(13) . . ?
C1 C10 C11 118.92(12) . . ?
C12 C11 C10 120.99(13) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 121.51(13) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C2 118.65(12) . . ?
C14 C13 C12 122.30(13) . . ?
C2 C13 C12 119.03(12) . . ?
C15 C14 C13 120.95(13) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.38(13) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C3 119.46(12) . . ?
C15 C16 C17 117.96(12) . . ?
C3 C16 C17 122.54(12) . . ?
C18 C17 C22 116.31(12) . . ?
C18 C17 C16 121.34(12) . . ?
C22 C17 C16 122.16(12) . . ?
C17 C18 C19 122.91(13) . . ?
C17 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C20 C19 C18 121.76(13) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 117.68(13) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 H20 121.2 . . ?
N1 C21 C20 125.99(13) . . ?
N1 C21 C22 113.33(13) . . ?
C20 C21 C22 120.65(13) . . ?
N2 C22 C17 126.07(13) . . ?
N2 C22 C21 113.22(12) . . ?
C17 C22 C21 120.68(12) . . ?
C21 N1 S1 105.98(10) . . ?
C22 N2 S1 106.03(10) . . ?
N1 S1 N2 101.44(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
C6 C1 C2 C13 178.77(11) . . . . ?
C10 C1 C2 C13 0.02(18) . . . . ?
C6 C1 C2 C3 0.29(18) . . . . ?
C10 C1 C2 C3 -178.46(11) . . . . ?
C13 C2 C3 C16 -3.05(18) . . . . ?
C1 C2 C3 C16 175.42(11) . . . . ?
C13 C2 C3 C4 179.59(11) . . . . ?
C1 C2 C3 C4 -1.94(18) . . . . ?
C16 C3 C4 C5 -175.63(13) . . . . ?
C2 C3 C4 C5 1.64(19) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C10 C1 C6 C7 2.18(19) . . . . ?
C2 C1 C6 C7 -176.57(12) . . . . ?
C10 C1 C6 C5 -179.55(12) . . . . ?
C2 C1 C6 C5 1.70(18) . . . . ?
C4 C5 C6 C7 176.16(13) . . . . ?
C4 C5 C6 C1 -2.05(19) . . . . ?
C1 C6 C7 C8 -0.8(2) . . . . ?
C5 C6 C7 C8 -179.05(13) . . . . ?
C6 C7 C8 C9 -1.1(2) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C8 C9 C10 C1 -0.3(2) . . . . ?
C8 C9 C10 C11 179.12(13) . . . . ?
C6 C1 C10 C9 -1.61(19) . . . . ?
C2 C1 C10 C9 177.14(12) . . . . ?
C6 C1 C10 C11 178.94(12) . . . . ?
C2 C1 C10 C11 -2.31(18) . . . . ?
C9 C10 C11 C12 -176.94(13) . . . . ?
C1 C10 C11 C12 2.5(2) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C3 C2 C13 C14 2.52(18) . . . . ?
C1 C2 C13 C14 -175.96(11) . . . . ?
C3 C2 C13 C12 -179.39(11) . . . . ?
C1 C2 C13 C12 2.13(18) . . . . ?
C11 C12 C13 C14 176.00(13) . . . . ?
C11 C12 C13 C2 -2.0(2) . . . . ?
C2 C13 C14 C15 0.2(2) . . . . ?
C12 C13 C14 C15 -177.82(12) . . . . ?
C13 C14 C15 C16 -2.4(2) . . . . ?
C14 C15 C16 C3 1.9(2) . . . . ?
C14 C15 C16 C17 179.71(12) . . . . ?
C2 C3 C16 C15 0.86(19) . . . . ?
C4 C3 C16 C15 178.10(12) . . . . ?
C2 C3 C16 C17 -176.87(11) . . . . ?
C4 C3 C16 C17 0.37(19) . . . . ?
C15 C16 C17 C18 -62.15(17) . . . . ?
C3 C16 C17 C18 115.61(15) . . . . ?
C15 C16 C17 C22 112.64(15) . . . . ?
C3 C16 C17 C22 -69.60(17) . . . . ?
C22 C17 C18 C19 0.6(2) . . . . ?
C16 C17 C18 C19 175.71(13) . . . . ?
C17 C18 C19 C20 -0.1(2) . . . . ?
C18 C19 C20 C21 -0.5(2) . . . . ?
C19 C20 C21 N1 -177.58(13) . . . . ?
C19 C20 C21 C22 0.4(2) . . . . ?
C18 C17 C22 N2 177.32(13) . . . . ?
C16 C17 C22 N2 2.3(2) . . . . ?
C18 C17 C22 C21 -0.68(19) . . . . ?
C16 C17 C22 C21 -175.71(12) . . . . ?
N1 C21 C22 N2 0.16(17) . . . . ?
C20 C21 C22 N2 -178.06(12) . . . . ?
N1 C21 C22 C17 178.40(12) . . . . ?
C20 C21 C22 C17 0.2(2) . . . . ?
C20 C21 N1 S1 177.74(12) . . . . ?
C22 C21 N1 S1 -0.37(14) . . . . ?
C17 C22 N2 S1 -178.00(11) . . . . ?
C21 C22 N2 S1 0.13(14) . . . . ?
C21 N1 S1 N2 0.41(11) . . . . ?
C22 N2 S1 N1 -0.32(11) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR IIP665                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_IIP667
_database_code_depnum_ccdc_archive 'CCDC 1576377'
_audit_update_record             
;
2017-09-25 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H6 F6 N2 Se'
_chemical_formula_sum            'C14 H6 F6 N2 Se'
_chemical_formula_weight         395.17
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
_space_group_IT_number           86
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   35.191(2)
_cell_length_b                   35.191
_cell_length_c                   4.3928(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5440.1(8)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.45
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             3072
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.361
_exptl_absorpt_correction_T_max  0.552

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0515
_diffrn_reflns_av_uneti/neti     0.0371
_diffrn_reflns_number            34119
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.952
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             6225
_reflns_number_gt                5193
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_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     
'w=1/[σ²(Fo²)+(0.0438P)²+36.4123P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6225
_refine_ls_number_parameters     409
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.198
_refine_diff_density_min         -1.027
_refine_diff_density_rms         0.116

#...............................................................................
# .RES SHELXL file: IIP667.res
# .HKL SHELXL file: IIP667.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Se1 Se 0.50686(2) 0.85557(2) 0.95099(12) 0.02567(14) Uani 1 1 d . . . . .
N1 N 0.48074(12) 0.89789(11) 0.8658(11) 0.0275(9) Uani 1 1 d . . . . .
N2 N 0.47440(11) 0.82488(11) 0.7572(10) 0.0245(9) Uani 1 1 d . . . . .
C1 C 0.44745(13) 0.84696(12) 0.6414(12) 0.0220(10) Uani 1 1 d . . . . .
C2 C 0.45104(13) 0.88729(13) 0.7011(12) 0.0252(10) Uani 1 1 d . . . . .
C3 C 0.42328(15) 0.91299(13) 0.5819(14) 0.0314(12) Uani 1 1 d . . . . .
H3 H 0.425380 0.939505 0.618726 0.038 Uiso 1 1 calc R U . . .
C4 C 0.39413(15) 0.89917(15) 0.4171(15) 0.0362(13) Uani 1 1 d . . . . .
H4 H 0.375829 0.916240 0.336052 0.043 Uiso 1 1 calc R U . . .
C5 C 0.39016(15) 0.85925(14) 0.3614(15) 0.0331(12) Uani 1 1 d . . . . .
H5 H 0.369022 0.850690 0.245681 0.040 Uiso 1 1 calc R U . . .
C6 C 0.41561(13) 0.83284(13) 0.4683(12) 0.0241(10) Uani 1 1 d . . . . .
C7 C 0.40990(13) 0.79166(13) 0.4139(12) 0.0245(10) Uani 1 1 d . . . . .
C8 C 0.37404(14) 0.77569(14) 0.4589(13) 0.0271(10) Uani 1 1 d . . . . .
H8 H 0.353592 0.791415 0.522620 0.032 Uiso 1 1 calc R U . . .
C9 C 0.36782(15) 0.73730(15) 0.4123(13) 0.0321(12) Uani 1 1 d . . . . .
C10 C 0.39680(17) 0.71392(15) 0.3170(13) 0.0350(13) Uani 1 1 d . . . . .
H10 H 0.392418 0.687654 0.281639 0.042 Uiso 1 1 calc R U . . .
C11 C 0.43256(16) 0.72957(14) 0.2736(13) 0.0318(12) Uani 1 1 d . . . . .
C12 C 0.43961(14) 0.76789(14) 0.3226(12) 0.0265(10) Uani 1 1 d . . . . .
H12 H 0.464436 0.777888 0.294301 0.032 Uiso 1 1 calc R U . . .
C13 C 0.3295(2) 0.72128(17) 0.4847(15) 0.0491(17) Uani 1 1 d D . . . .
C14 C 0.46426(19) 0.70441(16) 0.1652(14) 0.0466(16) Uani 1 1 d D . . . .
F1 F 0.3015(3) 0.7413(3) 0.322(2) 0.0528(11) Uani 0.481(7) 1 d D . P A 1
F2 F 0.3165(2) 0.7309(2) 0.776(2) 0.0528(11) Uani 0.481(7) 1 d D . P A 1
F3 F 0.3210(3) 0.6868(3) 0.442(3) 0.0528(11) Uani 0.481(7) 1 d D . P A 1
F1B F 0.3309(2) 0.7085(2) 0.7806(17) 0.0528(11) Uani 0.519(7) 1 d D . P A 2
F2B F 0.3272(3) 0.6865(2) 0.341(2) 0.0528(11) Uani 0.519(7) 1 d D . P A 2
F3B F 0.3020(3) 0.7418(3) 0.435(2) 0.0528(11) Uani 0.519(7) 1 d D . P A 2
F4 F 0.45529(17) 0.69126(17) -0.1165(15) 0.0488(9) Uani 0.601(5) 1 d D . P B 1
F5 F 0.45932(19) 0.66895(18) 0.3232(18) 0.0488(9) Uani 0.601(5) 1 d D . P B 1
F6 F 0.4969(2) 0.7142(2) 0.2158(18) 0.0488(9) Uani 0.601(5) 1 d D . P B 1
F4B F 0.4983(3) 0.7134(4) 0.342(3) 0.0488(9) Uani 0.399(5) 1 d D . P B 2
F5B F 0.4817(3) 0.7181(2) -0.113(2) 0.0488(9) Uani 0.399(5) 1 d D . P B 2
F6B F 0.4639(3) 0.6696(3) 0.170(3) 0.0488(9) Uani 0.399(5) 1 d D . P B 2
Se2 Se 0.51380(2) 0.95470(2) 0.27361(12) 0.02435(13) Uani 1 1 d . . . . .
N21 N 0.54986(11) 0.91860(10) 0.2577(10) 0.0218(8) Uani 1 1 d . . . . .
N22 N 0.54107(12) 0.98533(10) 0.5119(10) 0.0256(9) Uani 1 1 d . . . . .
C21 C 0.57886(13) 0.93094(12) 0.4272(11) 0.0196(9) Uani 1 1 d . . . . .
C22 C 0.57414(13) 0.96815(12) 0.5645(12) 0.0229(10) Uani 1 1 d . . . . .
C23 C 0.60411(16) 0.98452(14) 0.7422(13) 0.0335(12) Uani 1 1 d . . . . .
H23 H 0.600874 1.008396 0.839652 0.040 Uiso 1 1 calc R U . . .
C24 C 0.63717(15) 0.96508(14) 0.7676(13) 0.0308(11) Uani 1 1 d . . . . .
H24 H 0.657472 0.975948 0.880536 0.037 Uiso 1 1 calc R U . . .
C25 C 0.64235(14) 0.92889(13) 0.6302(12) 0.0238(10) Uani 1 1 d . . . . .
H25 H 0.666244 0.916614 0.651813 0.029 Uiso 1 1 calc R U . . .
C26 C 0.61421(12) 0.91086(12) 0.4670(11) 0.0199(9) Uani 1 1 d . . . . .
C27 C 0.62090(12) 0.87234(12) 0.3404(11) 0.0180(9) Uani 1 1 d . . . . .
C28 C 0.65535(12) 0.86391(12) 0.1979(11) 0.0187(9) Uani 1 1 d . . . . .
H28 H 0.673910 0.883294 0.174812 0.022 Uiso 1 1 calc R U . . .
C29 C 0.66288(12) 0.82772(12) 0.0897(10) 0.0176(9) Uani 1 1 d . . . . .
C30 C 0.63621(12) 0.79879(12) 0.1202(11) 0.0190(9) Uani 1 1 d . . . . .
H30 H 0.641162 0.774088 0.042493 0.023 Uiso 1 1 calc R U . . .
C31 C 0.60222(13) 0.80683(13) 0.2668(11) 0.0212(9) Uani 1 1 d . . . . .
C32 C 0.59428(12) 0.84310(12) 0.3731(11) 0.0193(9) Uani 1 1 d . . . . .
H32 H 0.570597 0.848108 0.468803 0.023 Uiso 1 1 calc R U . . .
C33 C 0.70046(13) 0.81943(14) -0.0549(12) 0.0233(10) Uani 1 1 d . . . . .
C34 C 0.57390(14) 0.77573(13) 0.3166(13) 0.0268(11) Uani 1 1 d . . . . .
F21 F 0.71315(9) 0.84912(9) -0.2182(8) 0.0409(8) Uani 1 1 d . . . . .
F22 F 0.72701(9) 0.81237(12) 0.1503(8) 0.0481(10) Uani 1 1 d . . . . .
F23 F 0.69939(9) 0.79028(9) -0.2418(8) 0.0414(8) Uani 1 1 d . . . . .
F24 F 0.55672(19) 0.77906(18) 0.5994(19) 0.0449(9) Uani 0.511(5) 1 d . . P C 1
F25 F 0.5844(3) 0.7426(2) 0.272(2) 0.0449(9) Uani 0.511(5) 1 d . . P C 1
F26 F 0.5421(2) 0.7823(2) 0.133(2) 0.0449(9) Uani 0.511(5) 1 d . . P C 1
F24B F 0.5827(3) 0.7440(3) 0.137(2) 0.0449(9) Uani 0.489(5) 1 d . . P C 2
F25B F 0.5399(2) 0.7838(2) 0.281(2) 0.0449(9) Uani 0.489(5) 1 d . . P C 2
F26B F 0.5786(2) 0.76094(19) 0.601(2) 0.0449(9) Uani 0.489(5) 1 d . . P C 2



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
Se1 N2 1.788(4) . ?
Se1 N1 1.790(4) . ?
N1 C2 1.325(7) . ?
N2 C1 1.327(6) . ?
C1 C6 1.443(7) . ?
C1 C2 1.449(6) . ?
C2 C3 1.431(7) . ?
C3 C4 1.346(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.433(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.482(6) . ?
C7 C8 1.396(7) . ?
C7 C12 1.398(7) . ?
C8 C9 1.384(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(8) . ?
C9 C13 1.495(8) . ?
C10 C11 1.387(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(7) . ?
C11 C14 1.502(8) . ?
C12 H12 0.9500 . ?
C13 F3B 1.227(10) . ?
C13 F3 1.263(11) . ?
C13 F1B 1.376(9) . ?
C13 F2B 1.380(10) . ?
C13 F2 1.399(10) . ?
C13 F1 1.408(11) . ?
C14 F6 1.219(9) . ?
C14 F6B 1.227(10) . ?
C14 F4 1.358(8) . ?
C14 F5 1.438(9) . ?
C14 F5B 1.450(10) . ?
C14 F4B 1.462(12) . ?
Se2 N22 1.783(4) . ?
Se2 N21 1.797(4) . ?
N21 C21 1.336(6) . ?
N22 C22 1.332(6) . ?
C21 C26 1.441(6) . ?
C21 C22 1.451(6) . ?
C22 C23 1.433(7) . ?
C23 C24 1.354(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.421(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.484(6) . ?
C27 C28 1.396(6) . ?
C27 C32 1.399(6) . ?
C28 C29 1.385(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.391(6) . ?
C29 C33 1.496(6) . ?
C30 C31 1.388(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.388(6) . ?
C31 C34 1.496(6) . ?
C32 H32 0.9500 . ?
C33 F23 1.314(6) . ?
C33 F22 1.322(6) . ?
C33 F21 1.344(6) . ?
C34 F25 1.237(10) . ?
C34 F25B 1.240(10) . ?
C34 F26B 1.362(10) . ?
C34 F24 1.386(9) . ?
C34 F26 1.399(11) . ?
C34 F24B 1.402(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Se1 N1 94.30(19) . . ?
C2 N1 Se1 106.6(3) . . ?
C1 N2 Se1 106.6(3) . . ?
N2 C1 C6 123.7(4) . . ?
N2 C1 C2 116.2(4) . . ?
C6 C1 C2 120.0(4) . . ?
N1 C2 C3 124.1(4) . . ?
N1 C2 C1 116.3(4) . . ?
C3 C2 C1 119.6(5) . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.4(5) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 122.8(5) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C1 117.0(4) . . ?
C5 C6 C7 121.2(5) . . ?
C1 C6 C7 121.8(4) . . ?
C8 C7 C12 118.4(4) . . ?
C8 C7 C6 119.6(4) . . ?
C12 C7 C6 122.0(4) . . ?
C9 C8 C7 121.0(5) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 120.8(5) . . ?
C10 C9 C13 120.5(5) . . ?
C8 C9 C13 118.6(5) . . ?
C9 C10 C11 118.5(5) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C10 C11 C12 121.8(5) . . ?
C10 C11 C14 118.9(5) . . ?
C12 C11 C14 119.3(5) . . ?
C11 C12 C7 119.5(5) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
F3B C13 F1B 112.9(8) . . ?
F3B C13 F2B 113.1(8) . . ?
F1B C13 F2B 98.4(6) . . ?
F3 C13 F2 106.9(7) . . ?
F3 C13 F1 103.8(8) . . ?
F2 C13 F1 96.5(8) . . ?
F3B C13 C9 116.8(7) . . ?
F3 C13 C9 122.9(7) . . ?
F1B C13 C9 107.0(6) . . ?
F2B C13 C9 106.9(6) . . ?
F2 C13 C9 113.5(6) . . ?
F1 C13 C9 109.6(6) . . ?
F6 C14 F4 118.8(7) . . ?
F6 C14 F5 105.8(6) . . ?
F4 C14 F5 96.7(6) . . ?
F6B C14 F5B 110.6(8) . . ?
F6B C14 F4B 102.4(8) . . ?
F5B C14 F4B 91.6(8) . . ?
F6 C14 C11 118.3(6) . . ?
F6B C14 C11 125.2(7) . . ?
F4 C14 C11 108.5(5) . . ?
F5 C14 C11 105.6(6) . . ?
F5B C14 C11 112.7(5) . . ?
F4B C14 C11 108.2(6) . . ?
N22 Se2 N21 94.02(18) . . ?
C21 N21 Se2 106.8(3) . . ?
C22 N22 Se2 107.3(3) . . ?
N21 C21 C26 124.6(4) . . ?
N21 C21 C22 115.9(4) . . ?
C26 C21 C22 119.4(4) . . ?
N22 C22 C23 123.7(4) . . ?
N22 C22 C21 116.0(4) . . ?
C23 C22 C21 120.3(4) . . ?
C24 C23 C22 118.3(5) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C23 C24 C25 121.9(5) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C26 C25 C24 122.8(5) . . ?
C26 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C25 C26 C21 117.3(4) . . ?
C25 C26 C27 120.1(4) . . ?
C21 C26 C27 122.6(4) . . ?
C28 C27 C32 118.1(4) . . ?
C28 C27 C26 120.0(4) . . ?
C32 C27 C26 121.8(4) . . ?
C29 C28 C27 121.0(4) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 120.7(4) . . ?
C28 C29 C33 119.6(4) . . ?
C30 C29 C33 119.6(4) . . ?
C31 C30 C29 118.5(4) . . ?
C31 C30 H30 120.8 . . ?
C29 C30 H30 120.8 . . ?
C30 C31 C32 121.2(4) . . ?
C30 C31 C34 119.5(4) . . ?
C32 C31 C34 119.3(4) . . ?
C31 C32 C27 120.5(4) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?
F23 C33 F22 107.4(4) . . ?
F23 C33 F21 106.4(4) . . ?
F22 C33 F21 106.0(4) . . ?
F23 C33 C29 113.1(4) . . ?
F22 C33 C29 111.8(4) . . ?
F21 C33 C29 111.6(4) . . ?
F25B C34 F26B 108.7(6) . . ?
F25 C34 F24 110.6(6) . . ?
F25 C34 F26 107.6(6) . . ?
F24 C34 F26 98.9(6) . . ?
F25B C34 F24B 108.9(7) . . ?
F26B C34 F24B 100.7(6) . . ?
F25 C34 C31 117.8(6) . . ?
F25B C34 C31 117.2(5) . . ?
F26B C34 C31 109.4(5) . . ?
F24 C34 C31 111.1(5) . . ?
F26 C34 C31 109.1(5) . . ?
F24B C34 C31 110.7(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Se1 N1 C2 -1.0(4) . . . . ?
N1 Se1 N2 C1 0.9(4) . . . . ?
Se1 N2 C1 C6 -179.7(4) . . . . ?
Se1 N2 C1 C2 -0.5(5) . . . . ?
Se1 N1 C2 C3 -178.9(4) . . . . ?
Se1 N1 C2 C1 0.9(6) . . . . ?
N2 C1 C2 N1 -0.2(7) . . . . ?
C6 C1 C2 N1 178.9(5) . . . . ?
N2 C1 C2 C3 179.5(5) . . . . ?
C6 C1 C2 C3 -1.3(7) . . . . ?
N1 C2 C3 C4 -180.0(6) . . . . ?
C1 C2 C3 C4 0.3(8) . . . . ?
C2 C3 C4 C5 0.7(9) . . . . ?
C3 C4 C5 C6 -0.6(10) . . . . ?
C4 C5 C6 C1 -0.4(8) . . . . ?
C4 C5 C6 C7 178.1(5) . . . . ?
N2 C1 C6 C5 -179.6(5) . . . . ?
C2 C1 C6 C5 1.3(7) . . . . ?
N2 C1 C6 C7 1.9(8) . . . . ?
C2 C1 C6 C7 -177.2(5) . . . . ?
C5 C6 C7 C8 -45.2(8) . . . . ?
C1 C6 C7 C8 133.2(5) . . . . ?
C5 C6 C7 C12 135.8(6) . . . . ?
C1 C6 C7 C12 -45.7(8) . . . . ?
C12 C7 C8 C9 -0.5(8) . . . . ?
C6 C7 C8 C9 -179.5(5) . . . . ?
C7 C8 C9 C10 -0.7(9) . . . . ?
C7 C8 C9 C13 175.8(5) . . . . ?
C8 C9 C10 C11 1.1(9) . . . . ?
C13 C9 C10 C11 -175.4(5) . . . . ?
C9 C10 C11 C12 -0.3(9) . . . . ?
C9 C10 C11 C14 -179.1(5) . . . . ?
C10 C11 C12 C7 -1.0(8) . . . . ?
C14 C11 C12 C7 177.9(5) . . . . ?
C8 C7 C12 C11 1.3(8) . . . . ?
C6 C7 C12 C11 -179.7(5) . . . . ?
C10 C9 C13 F3B -148.1(8) . . . . ?
C8 C9 C13 F3B 35.3(9) . . . . ?
C10 C9 C13 F3 -5.3(11) . . . . ?
C8 C9 C13 F3 178.1(8) . . . . ?
C10 C9 C13 F1B 84.3(7) . . . . ?
C8 C9 C13 F1B -92.3(7) . . . . ?
C10 C9 C13 F2B -20.3(9) . . . . ?
C8 C9 C13 F2B 163.1(7) . . . . ?
C10 C9 C13 F2 125.9(7) . . . . ?
C8 C9 C13 F2 -50.7(8) . . . . ?
C10 C9 C13 F1 -127.5(8) . . . . ?
C8 C9 C13 F1 55.9(9) . . . . ?
C10 C11 C14 F6 -157.6(7) . . . . ?
C12 C11 C14 F6 23.5(9) . . . . ?
C10 C11 C14 F6B -16.2(11) . . . . ?
C12 C11 C14 F6B 164.9(9) . . . . ?
C10 C11 C14 F4 63.2(7) . . . . ?
C12 C11 C14 F4 -115.7(6) . . . . ?
C10 C11 C14 F5 -39.5(7) . . . . ?
C12 C11 C14 F5 141.6(6) . . . . ?
C10 C11 C14 F5B 123.5(7) . . . . ?
C12 C11 C14 F5B -55.4(8) . . . . ?
C10 C11 C14 F4B -136.8(8) . . . . ?
C12 C11 C14 F4B 44.3(9) . . . . ?
N22 Se2 N21 C21 0.6(3) . . . . ?
N21 Se2 N22 C22 0.3(4) . . . . ?
Se2 N21 C21 C26 -178.0(4) . . . . ?
Se2 N21 C21 C22 -1.2(5) . . . . ?
Se2 N22 C22 C23 178.5(4) . . . . ?
Se2 N22 C22 C21 -1.0(5) . . . . ?
N21 C21 C22 N22 1.6(7) . . . . ?
C26 C21 C22 N22 178.5(4) . . . . ?
N21 C21 C22 C23 -177.9(5) . . . . ?
C26 C21 C22 C23 -1.0(7) . . . . ?
N22 C22 C23 C24 -176.9(5) . . . . ?
C21 C22 C23 C24 2.6(8) . . . . ?
C22 C23 C24 C25 -1.6(8) . . . . ?
C23 C24 C25 C26 -1.1(8) . . . . ?
C24 C25 C26 C21 2.6(7) . . . . ?
C24 C25 C26 C27 -177.4(5) . . . . ?
N21 C21 C26 C25 175.1(5) . . . . ?
C22 C21 C26 C25 -1.5(7) . . . . ?
N21 C21 C26 C27 -4.9(7) . . . . ?
C22 C21 C26 C27 178.4(4) . . . . ?
C25 C26 C27 C28 -43.5(7) . . . . ?
C21 C26 C27 C28 136.6(5) . . . . ?
C25 C26 C27 C32 133.1(5) . . . . ?
C21 C26 C27 C32 -46.9(7) . . . . ?
C32 C27 C28 C29 0.5(7) . . . . ?
C26 C27 C28 C29 177.2(4) . . . . ?
C27 C28 C29 C30 0.0(7) . . . . ?
C27 C28 C29 C33 -178.5(4) . . . . ?
C28 C29 C30 C31 -1.2(7) . . . . ?
C33 C29 C30 C31 177.3(4) . . . . ?
C29 C30 C31 C32 1.9(7) . . . . ?
C29 C30 C31 C34 -176.9(4) . . . . ?
C30 C31 C32 C27 -1.4(7) . . . . ?
C34 C31 C32 C27 177.4(4) . . . . ?
C28 C27 C32 C31 0.2(7) . . . . ?
C26 C27 C32 C31 -176.5(4) . . . . ?
C28 C29 C33 F23 -156.4(4) . . . . ?
C30 C29 C33 F23 25.1(6) . . . . ?
C28 C29 C33 F22 82.2(6) . . . . ?
C30 C29 C33 F22 -96.4(5) . . . . ?
C28 C29 C33 F21 -36.4(6) . . . . ?
C30 C29 C33 F21 145.1(4) . . . . ?
C30 C31 C34 F25 12.1(9) . . . . ?
C32 C31 C34 F25 -166.8(7) . . . . ?
C30 C31 C34 F25B -140.1(7) . . . . ?
C32 C31 C34 F25B 41.0(9) . . . . ?
C30 C31 C34 F26B 95.5(6) . . . . ?
C32 C31 C34 F26B -83.3(6) . . . . ?
C30 C31 C34 F24 141.1(5) . . . . ?
C32 C31 C34 F24 -37.8(7) . . . . ?
C30 C31 C34 F26 -111.0(6) . . . . ?
C32 C31 C34 F26 70.2(7) . . . . ?
C30 C31 C34 F24B -14.5(8) . . . . ?
C32 C31 C34 F24B 166.6(6) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR IIP667                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_IIR622
_database_code_depnum_ccdc_archive 'CCDC 1564844'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
'4,7-Bis(3,5-bis(trifluoromethyl)phenyl)benzo[c][1,2,5]thiadiazole '
_chemical_formula_moiety         'C22 H8 F12 N2 S'
_chemical_formula_sum            'C22 H8 F12 N2 S'
_chemical_formula_weight         560.36
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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                   8.3373(17)
_cell_length_b                   23.536(5)
_cell_length_c                   11.577(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.527(7)
_cell_angle_gamma                90
_cell_volume                     2113.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7440
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.44
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.510
_exptl_crystal_size_min          0.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1112
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.727
_exptl_absorpt_correction_T_max  0.909

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_r_equivalents  0.0525
_diffrn_reflns_av_uneti/neti     0.0530
_diffrn_reflns_number            15301
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.981
_reflns_number_total             4745
_reflns_number_gt                3865
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_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     
'w=1/[σ²(Fo²)+(0.0684P)²+4.6844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4745
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.1858
_refine_ls_wR_factor_gt          0.1760
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.100

#...............................................................................
# .RES SHELXL file: IIR622.res
# .HKL SHELXL file: IIR622.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

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
C1 C 0.1688(4) 0.48045(12) 0.6663(3) 0.0166(6) Uani 1 1 d . . . . .
C2 C 0.1854(4) 0.44105(13) 0.5765(3) 0.0163(6) Uani 1 1 d . . . . .
C3 C 0.2498(4) 0.45895(13) 0.4837(3) 0.0169(6) Uani 1 1 d . . . . .
C4 C 0.2890(4) 0.51562(13) 0.4830(3) 0.0188(6) Uani 1 1 d . . . . .
H4 H 0.328597 0.529308 0.420924 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2722(4) 0.55449(13) 0.5720(3) 0.0191(6) Uani 1 1 d . . . . .
H5 H 0.300305 0.593255 0.566412 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2174(4) 0.53865(13) 0.6656(3) 0.0171(6) Uani 1 1 d . . . . .
C7 C 0.2106(4) 0.57957(12) 0.7610(3) 0.0170(6) Uani 1 1 d . . . . .
C8 C 0.1517(4) 0.63520(13) 0.7264(3) 0.0212(6) Uani 1 1 d . . . . .
H8 H 0.112985 0.646383 0.641764 0.025 Uiso 1 1 calc R U . . .
C9 C 0.1506(4) 0.67385(13) 0.8172(3) 0.0235(7) Uani 1 1 d . . . . .
C10 C 0.2083(4) 0.65892(14) 0.9410(3) 0.0236(7) Uani 1 1 d . . . . .
H10 H 0.206322 0.685671 1.001944 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2695(4) 0.60396(13) 0.9753(3) 0.0200(6) Uani 1 1 d . . . . .
C12 C 0.2680(4) 0.56419(13) 0.8857(3) 0.0187(6) Uani 1 1 d . . . . .
H12 H 0.306232 0.526474 0.909847 0.022 Uiso 1 1 calc R U . . .
C13 C 0.0908(5) 0.73375(15) 0.7791(4) 0.0328(8) Uani 1 1 d . . . . .
C14 C 0.3425(5) 0.58880(15) 1.1110(3) 0.0267(7) Uani 1 1 d . . . . .
C15 C 0.2747(4) 0.41799(12) 0.3937(3) 0.0168(6) Uani 1 1 d . . . . .
C16 C 0.2282(4) 0.43267(13) 0.2693(3) 0.0170(6) Uani 1 1 d . . . . .
H16 H 0.177489 0.468650 0.240717 0.020 Uiso 1 1 calc R U . . .
C17 C 0.2560(4) 0.39468(13) 0.1871(3) 0.0188(6) Uani 1 1 d . . . . .
C18 C 0.3288(5) 0.34169(14) 0.2264(3) 0.0245(7) Uani 1 1 d . . . . .
H18 H 0.347537 0.315897 0.169519 0.029 Uiso 1 1 calc R U . . .
C19 C 0.3734(5) 0.32726(14) 0.3496(3) 0.0253(7) Uani 1 1 d . . . . .
C20 C 0.3464(4) 0.36455(14) 0.4342(3) 0.0220(7) Uani 1 1 d . . . . .
H20 H 0.376588 0.353759 0.518652 0.026 Uiso 1 1 calc R U . . .
C21 C 0.2065(4) 0.40934(14) 0.0522(3) 0.0224(7) Uani 1 1 d . . . . .
C22 C 0.4593(6) 0.27123(17) 0.3941(4) 0.0402(10) Uani 1 1 d . . . . .
F1 F -0.0225(4) 0.73688(10) 0.6630(3) 0.0572(8) Uani 1 1 d . . . . .
F2 F 0.2219(4) 0.76801(10) 0.7852(3) 0.0516(7) Uani 1 1 d . . . . .
F3 F 0.0163(4) 0.75680(10) 0.8521(3) 0.0567(8) Uani 1 1 d . . . . .
F4 F 0.4730(7) 0.62092(16) 1.1757(4) 0.0623(14) Uani 0.805(6) 1 d . . P A 1
F5 F 0.2310(5) 0.5882(3) 1.1656(3) 0.0764(19) Uani 0.805(6) 1 d . . P A 1
F6 F 0.4148(7) 0.53571(13) 1.1333(3) 0.0534(11) Uani 0.805(6) 1 d . . P A 1
F4B F 0.301(3) 0.5431(8) 1.1269(13) 0.0623(14) Uani 0.195(6) 1 d . . P A 2
F5B F 0.497(3) 0.6002(13) 1.1511(18) 0.0764(19) Uani 0.195(6) 1 d . . P A 2
F6B F 0.280(3) 0.6295(6) 1.1697(12) 0.0534(11) Uani 0.195(6) 1 d . . P A 2
F7 F 0.1017(3) 0.45387(10) 0.01880(19) 0.0371(6) Uani 1 1 d . . . . .
F8 F 0.3429(3) 0.42090(11) 0.0231(2) 0.0388(6) Uani 1 1 d . . . . .
F9 F 0.1231(3) 0.36615(10) -0.0215(2) 0.0398(6) Uani 1 1 d . . . . .
F10 F 0.6294(4) 0.27555(13) 0.4253(3) 0.0693(10) Uani 1 1 d . . . . .
F11 F 0.4062(6) 0.23144(12) 0.3076(3) 0.0908(14) Uani 1 1 d . . . . .
F12 F 0.4341(4) 0.25153(11) 0.4937(3) 0.0545(8) Uani 1 1 d . . . . .
N1 N 0.1013(4) 0.45684(11) 0.7445(2) 0.0209(6) Uani 1 1 d . . . . .
N2 N 0.1300(4) 0.38830(11) 0.5886(2) 0.0216(6) Uani 1 1 d . . . . .
S1 S 0.06530(12) 0.39100(3) 0.70383(8) 0.0239(2) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
C1 N1 1.349(4) . ?
C1 C6 1.429(4) . ?
C1 C2 1.437(4) . ?
C2 N2 1.350(4) . ?
C2 C3 1.430(4) . ?
C3 C4 1.374(4) . ?
C3 C15 1.489(4) . ?
C4 C5 1.423(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.483(4) . ?
C7 C12 1.392(4) . ?
C7 C8 1.404(4) . ?
C8 C9 1.392(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(5) . ?
C9 C13 1.506(5) . ?
C10 C11 1.394(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(4) . ?
C11 C14 1.505(5) . ?
C12 H12 0.9500 . ?
C13 F1 1.331(5) . ?
C13 F3 1.334(5) . ?
C13 F2 1.340(5) . ?
C14 F4B 1.165(14) . ?
C14 F5B 1.22(2) . ?
C14 F5 1.301(5) . ?
C14 F4 1.311(5) . ?
C14 F6 1.370(5) . ?
C14 F6B 1.381(14) . ?
C15 C16 1.391(4) . ?
C15 C20 1.398(4) . ?
C16 C17 1.386(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(4) . ?
C17 C21 1.502(4) . ?
C18 C19 1.378(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(5) . ?
C19 C22 1.499(5) . ?
C20 H20 0.9500 . ?
C21 F7 1.328(4) . ?
C21 F8 1.328(4) . ?
C21 F9 1.345(4) . ?
C22 F11 1.323(5) . ?
C22 F12 1.329(5) . ?
C22 F10 1.333(6) . ?
N1 S1 1.615(3) . ?
N2 S1 1.613(3) . ?

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
N1 C1 C6 126.0(3) . . ?
N1 C1 C2 113.2(3) . . ?
C6 C1 C2 120.8(3) . . ?
N2 C2 C3 125.9(3) . . ?
N2 C2 C1 113.0(3) . . ?
C3 C2 C1 121.0(3) . . ?
C4 C3 C2 116.5(3) . . ?
C4 C3 C15 122.0(3) . . ?
C2 C3 C15 121.5(3) . . ?
C3 C4 C5 122.2(3) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 123.1(3) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C6 C1 116.2(3) . . ?
C5 C6 C7 121.8(3) . . ?
C1 C6 C7 122.0(3) . . ?
C12 C7 C8 119.3(3) . . ?
C12 C7 C6 120.8(3) . . ?
C8 C7 C6 119.9(3) . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 C13 119.6(3) . . ?
C8 C9 C13 118.9(3) . . ?
C9 C10 C11 118.9(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 C14 118.9(3) . . ?
C12 C11 C14 120.5(3) . . ?
C7 C12 C11 120.2(3) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
F1 C13 F3 107.1(3) . . ?
F1 C13 F2 106.4(3) . . ?
F3 C13 F2 106.4(3) . . ?
F1 C13 C9 112.5(3) . . ?
F3 C13 C9 112.1(3) . . ?
F2 C13 C9 111.8(3) . . ?
F4B C14 F5B 118.3(16) . . ?
F5 C14 F4 108.7(4) . . ?
F5 C14 F6 104.0(4) . . ?
F4 C14 F6 101.7(4) . . ?
F4B C14 F6B 112.0(14) . . ?
F5B C14 F6B 101.1(14) . . ?
F4B C14 C11 110.7(7) . . ?
F5B C14 C11 108.1(9) . . ?
F5 C14 C11 114.9(3) . . ?
F4 C14 C11 113.1(3) . . ?
F6 C14 C11 113.2(3) . . ?
F6B C14 C11 105.5(6) . . ?
C16 C15 C20 119.6(3) . . ?
C16 C15 C3 120.4(3) . . ?
C20 C15 C3 120.0(3) . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.2(3) . . ?
C16 C17 C21 120.9(3) . . ?
C18 C17 C21 117.9(3) . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C20 121.4(3) . . ?
C18 C19 C22 119.0(3) . . ?
C20 C19 C22 119.5(3) . . ?
C19 C20 C15 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?
F7 C21 F8 107.3(3) . . ?
F7 C21 F9 106.3(3) . . ?
F8 C21 F9 106.6(3) . . ?
F7 C21 C17 112.6(3) . . ?
F8 C21 C17 112.1(3) . . ?
F9 C21 C17 111.5(3) . . ?
F11 C22 F12 107.1(4) . . ?
F11 C22 F10 106.7(4) . . ?
F12 C22 F10 106.4(3) . . ?
F11 C22 C19 112.2(3) . . ?
F12 C22 C19 113.4(3) . . ?
F10 C22 C19 110.7(4) . . ?
C1 N1 S1 106.1(2) . . ?
C2 N2 S1 106.3(2) . . ?
N2 S1 N1 101.32(14) . . ?

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
N1 C1 C2 N2 0.0(4) . . . . ?
C6 C1 C2 N2 -178.5(3) . . . . ?
N1 C1 C2 C3 178.2(3) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
N2 C2 C3 C4 175.8(3) . . . . ?
C1 C2 C3 C4 -2.1(4) . . . . ?
N2 C2 C3 C15 -4.8(5) . . . . ?
C1 C2 C3 C15 177.3(3) . . . . ?
C2 C3 C4 C5 2.0(5) . . . . ?
C15 C3 C4 C5 -177.3(3) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C1 -2.9(5) . . . . ?
C4 C5 C6 C7 176.5(3) . . . . ?
N1 C1 C6 C5 -175.5(3) . . . . ?
C2 C1 C6 C5 2.8(4) . . . . ?
N1 C1 C6 C7 5.0(5) . . . . ?
C2 C1 C6 C7 -176.7(3) . . . . ?
C5 C6 C7 C12 -136.8(3) . . . . ?
C1 C6 C7 C12 42.7(4) . . . . ?
C5 C6 C7 C8 40.8(4) . . . . ?
C1 C6 C7 C8 -139.7(3) . . . . ?
C12 C7 C8 C9 -0.5(5) . . . . ?
C6 C7 C8 C9 -178.1(3) . . . . ?
C7 C8 C9 C10 0.9(5) . . . . ?
C7 C8 C9 C13 178.7(3) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C13 C9 C10 C11 -177.5(3) . . . . ?
C9 C10 C11 C12 -1.8(5) . . . . ?
C9 C10 C11 C14 176.3(3) . . . . ?
C8 C7 C12 C11 -1.0(5) . . . . ?
C6 C7 C12 C11 176.6(3) . . . . ?
C10 C11 C12 C7 2.2(5) . . . . ?
C14 C11 C12 C7 -175.8(3) . . . . ?
C10 C9 C13 F1 -153.9(4) . . . . ?
C8 C9 C13 F1 28.2(5) . . . . ?
C10 C9 C13 F3 -33.1(5) . . . . ?
C8 C9 C13 F3 149.1(3) . . . . ?
C10 C9 C13 F2 86.4(4) . . . . ?
C8 C9 C13 F2 -91.5(4) . . . . ?
C10 C11 C14 F4B 140.5(15) . . . . ?
C12 C11 C14 F4B -41.5(16) . . . . ?
C10 C11 C14 F5B -88.5(15) . . . . ?
C12 C11 C14 F5B 89.5(14) . . . . ?
C10 C11 C14 F5 67.2(5) . . . . ?
C12 C11 C14 F5 -114.7(5) . . . . ?
C10 C11 C14 F4 -58.4(5) . . . . ?
C12 C11 C14 F4 119.7(4) . . . . ?
C10 C11 C14 F6 -173.4(4) . . . . ?
C12 C11 C14 F6 4.6(5) . . . . ?
C10 C11 C14 F6B 19.0(10) . . . . ?
C12 C11 C14 F6B -162.9(10) . . . . ?
C4 C3 C15 C16 -42.5(4) . . . . ?
C2 C3 C15 C16 138.2(3) . . . . ?
C4 C3 C15 C20 137.0(3) . . . . ?
C2 C3 C15 C20 -42.3(4) . . . . ?
C20 C15 C16 C17 -1.1(5) . . . . ?
C3 C15 C16 C17 178.4(3) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C15 C16 C17 C21 179.8(3) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C21 C17 C18 C19 -179.3(3) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
C17 C18 C19 C22 -177.3(4) . . . . ?
C18 C19 C20 C15 -0.8(5) . . . . ?
C22 C19 C20 C15 176.6(3) . . . . ?
C16 C15 C20 C19 1.2(5) . . . . ?
C3 C15 C20 C19 -178.2(3) . . . . ?
C16 C17 C21 F7 -14.9(4) . . . . ?
C18 C17 C21 F7 164.5(3) . . . . ?
C16 C17 C21 F8 106.3(4) . . . . ?
C18 C17 C21 F8 -74.3(4) . . . . ?
C16 C17 C21 F9 -134.3(3) . . . . ?
C18 C17 C21 F9 45.1(4) . . . . ?
C18 C19 C22 F11 -32.8(6) . . . . ?
C20 C19 C22 F11 149.8(4) . . . . ?
C18 C19 C22 F12 -154.3(4) . . . . ?
C20 C19 C22 F12 28.3(6) . . . . ?
C18 C19 C22 F10 86.2(4) . . . . ?
C20 C19 C22 F10 -91.2(4) . . . . ?
C6 C1 N1 S1 178.5(3) . . . . ?
C2 C1 N1 S1 0.1(3) . . . . ?
C3 C2 N2 S1 -178.2(3) . . . . ?
C1 C2 N2 S1 -0.1(3) . . . . ?
C2 N2 S1 N1 0.2(2) . . . . ?
C1 N1 S1 N2 -0.1(2) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR IIR622                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
