# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_gb075_1
_database_code_depnum_ccdc_archive 'CCDC 1416726'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_date             2014-11-27T15:44:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_contact_author            'V. Kahlenberg'

_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C12 H10 F13 I N2 S'
_chemical_formula_moiety         'C12 H10 F13 N2 S, I'

_chemical_formula_weight         588.18

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4269(3)
_cell_length_b                   8.9443(5)
_cell_length_c                   16.3677(9)
_cell_angle_alpha                85.570(5)
_cell_angle_beta                 81.795(4)
_cell_angle_gamma                86.766(5)
_cell_volume                     927.49(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3070
_cell_measurement_theta_min      3.202
_cell_measurement_theta_max      26.915

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

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    2.106
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.9586
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3575
_diffrn_orient_matrix_ub_11      0.0029913
_diffrn_orient_matrix_ub_12      -0.0698552
_diffrn_orient_matrix_ub_13      -0.0180082
_diffrn_orient_matrix_ub_21      0.0359514
_diffrn_orient_matrix_ub_22      -0.0367129
_diffrn_orient_matrix_ub_23      0.0357063
_diffrn_orient_matrix_ub_31      -0.105633
_diffrn_orient_matrix_ub_32      -0.010603
_diffrn_orient_matrix_ub_33      0.0180891
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_number            5693
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             3363
_reflns_number_gt                2961
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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     
'calc w=1/[σ²(Fo²)+(0.0175P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3363
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.056
_refine_ls_wR_factor_gt          0.0522
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.091

#----------------------------------------------------------------------------#
#                   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 0 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.65063(3) 0.74427(2) 0.597921(13) 0.02576(8) Uani 1 1 d . . .
S S 0.24377(13) 0.41099(13) 0.64232(6) 0.0468(3) Uani 1 1 d . . .
F7 F 0.2900(3) 0.6271(2) 1.09886(12) 0.0421(5) Uani 1 1 d . . .
F5 F -0.0110(3) 0.7525(2) 1.01270(12) 0.0375(5) Uani 1 1 d . . .
F3 F 0.2705(4) 0.5268(2) 0.95394(12) 0.0492(6) Uani 1 1 d . . .
F4 F 0.4687(3) 0.6956(3) 0.88636(12) 0.0492(7) Uani 1 1 d . . .
F6 F 0.2041(3) 0.9162(2) 0.94947(11) 0.0363(5) Uani 1 1 d . . .
F8 F 0.5195(3) 0.7777(3) 1.03212(11) 0.0398(6) Uani 1 1 d . . .
F11 F 0.3344(3) 0.7359(3) 1.24292(12) 0.0470(6) Uani 1 1 d . . .
F9 F 0.0448(3) 0.8666(3) 1.15420(12) 0.0435(6) Uani 1 1 d . . .
F1 F -0.0553(3) 0.6365(3) 0.87284(13) 0.0520(7) Uani 1 1 d . . .
F2 F 0.1417(4) 0.8046(2) 0.80615(12) 0.0543(7) Uani 1 1 d . . .
N1 N 0.0317(4) 0.1751(3) 0.60535(16) 0.0249(6) Uani 1 1 d . . .
F13 F 0.3060(4) 0.9738(3) 1.24791(12) 0.0540(7) Uani 1 1 d . . .
F10 F 0.2754(4) 1.0182(2) 1.08879(12) 0.0477(6) Uani 1 1 d . . .
F12 F 0.5742(3) 0.8709(3) 1.17655(13) 0.0603(8) Uani 1 1 d . . .
C7 C 0.1458(5) 0.6643(4) 0.8429(2) 0.0250(8) Uani 1 1 d . . .
C1 C 0.0411(5) 0.3221(4) 0.60963(18) 0.0218(7) Uani 1 1 d . . .
C8 C 0.2701(5) 0.6663(4) 0.91713(19) 0.0241(8) Uani 1 1 d . . .
C9 C 0.1919(5) 0.7763(4) 0.98402(19) 0.0222(7) Uani 1 1 d . . .
C6 C 0.2378(5) 0.5529(4) 0.7823(2) 0.0283(8) Uani 1 1 d . . .
H6A H 0.254 0.4534 0.8123 0.034 Uiso 1 1 calc R . .
H6B H 0.3796 0.5835 0.757 0.034 Uiso 1 1 calc R . .
C10 C 0.3148(5) 0.7634(4) 1.05949(19) 0.0235(7) Uani 1 1 d . . .
N2 N -0.1235(4) 0.3885(3) 0.57703(16) 0.0234(6) Uani 1 1 d D . .
H2 H -0.161(5) 0.484(2) 0.579(2) 0.028 Uiso 1 1 d D . .
C3 C -0.1391(5) 0.1487(4) 0.5682(2) 0.0313(8) Uani 1 1 d . . .
H3 H -0.1805 0.0531 0.5567 0.038 Uiso 1 1 calc R . .
C2 C -0.2373(5) 0.2800(4) 0.5511(2) 0.0289(8) Uani 1 1 d . . .
H2A H -0.3617 0.2957 0.5259 0.035 Uiso 1 1 calc R . .
C11 C 0.2483(5) 0.8795(4) 1.1243(2) 0.0281(8) Uani 1 1 d . . .
C027 C 0.1854(6) 0.0593(5) 0.6313(2) 0.0463(11) Uani 1 1 d . . .
H02A H 0.3091 0.0556 0.5887 0.069 Uiso 1 1 calc R . .
H02B H 0.1213 -0.0385 0.6387 0.069 Uiso 1 1 calc R . .
H02C H 0.2281 0.0838 0.6836 0.069 Uiso 1 1 calc R . .
C12 C 0.3691(5) 0.8654(5) 1.1995(2) 0.0334(9) Uani 1 1 d . . .
C5 C 0.1047(5) 0.5392(5) 0.7145(2) 0.0383(10) Uani 1 1 d . . .
H5A H 0.0809 0.6387 0.6856 0.046 Uiso 1 1 calc R . .
H5B H -0.0337 0.5001 0.7383 0.046 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   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
S C1 1.731(3) . ?
S C5 1.817(3) . ?
F7 C10 1.341(4) . ?
F5 C9 1.344(4) . ?
F3 C8 1.343(4) . ?
F4 C8 1.337(4) . ?
F6 C9 1.335(4) . ?
F8 C10 1.338(3) . ?
F11 C12 1.325(4) . ?
F9 C11 1.337(4) . ?
F1 C7 1.344(4) . ?
F2 C7 1.350(4) . ?
N1 C1 1.327(4) . ?
N1 C3 1.368(4) . ?
N1 C027 1.471(4) . ?
F13 C12 1.310(4) . ?
F10 C11 1.339(4) . ?
F12 C12 1.320(4) . ?
C7 C6 1.498(4) . ?
C7 C8 1.547(4) . ?
C1 N2 1.341(4) . ?
C8 C9 1.540(4) . ?
C9 C10 1.552(4) . ?
C6 C5 1.511(4) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C10 C11 1.542(4) . ?
N2 C2 1.374(4) . ?
N2 H2 0.877(18) . ?
C3 C2 1.332(5) . ?
C3 H3 0.95 . ?
C2 H2A 0.95 . ?
C11 C12 1.540(4) . ?
C027 H02A 0.98 . ?
C027 H02B 0.98 . ?
C027 H02C 0.98 . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S C5 102.76(15) . . ?
C1 N1 C3 108.7(3) . . ?
C1 N1 C027 126.1(3) . . ?
C3 N1 C027 125.1(3) . . ?
F1 C7 F2 105.8(3) . . ?
F1 C7 C6 111.3(3) . . ?
F2 C7 C6 110.9(3) . . ?
F1 C7 C8 108.1(3) . . ?
F2 C7 C8 107.5(3) . . ?
C6 C7 C8 112.9(3) . . ?
N1 C1 N2 107.6(2) . . ?
N1 C1 S 125.6(2) . . ?
N2 C1 S 126.6(3) . . ?
F4 C8 F3 107.7(2) . . ?
F4 C8 C9 108.5(3) . . ?
F3 C8 C9 107.9(3) . . ?
F4 C8 C7 107.3(3) . . ?
F3 C8 C7 107.0(3) . . ?
C9 C8 C7 118.1(2) . . ?
F6 C9 F5 108.2(2) . . ?
F6 C9 C8 108.6(3) . . ?
F5 C9 C8 109.0(2) . . ?
F6 C9 C10 108.3(2) . . ?
F5 C9 C10 107.5(3) . . ?
C8 C9 C10 115.0(2) . . ?
C7 C6 C5 113.0(3) . . ?
C7 C6 H6A 109 . . ?
C5 C6 H6A 109 . . ?
C7 C6 H6B 109 . . ?
C5 C6 H6B 109 . . ?
H6A C6 H6B 107.8 . . ?
F8 C10 F7 108.4(2) . . ?
F8 C10 C11 107.8(3) . . ?
F7 C10 C11 107.0(3) . . ?
F8 C10 C9 108.7(3) . . ?
F7 C10 C9 109.0(3) . . ?
C11 C10 C9 115.7(3) . . ?
C1 N2 C2 108.9(3) . . ?
C1 N2 H2 124.6(19) . . ?
C2 N2 H2 126(2) . . ?
C2 C3 N1 108.2(3) . . ?
C2 C3 H3 125.9 . . ?
N1 C3 H3 125.9 . . ?
C3 C2 N2 106.6(3) . . ?
C3 C2 H2A 126.7 . . ?
N2 C2 H2A 126.7 . . ?
F9 C11 F10 108.8(3) . . ?
F9 C11 C12 106.6(3) . . ?
F10 C11 C12 106.7(3) . . ?
F9 C11 C10 109.4(3) . . ?
F10 C11 C10 109.6(3) . . ?
C12 C11 C10 115.5(3) . . ?
N1 C027 H02A 109.5 . . ?
N1 C027 H02B 109.5 . . ?
H02A C027 H02B 109.5 . . ?
N1 C027 H02C 109.5 . . ?
H02A C027 H02C 109.5 . . ?
H02B C027 H02C 109.5 . . ?
F13 C12 F12 109.2(3) . . ?
F13 C12 F11 108.1(3) . . ?
F12 C12 F11 107.4(3) . . ?
F13 C12 C11 109.8(3) . . ?
F12 C12 C11 111.5(3) . . ?
F11 C12 C11 110.7(3) . . ?
C6 C5 S 108.0(2) . . ?
C6 C5 H5A 110.1 . . ?
S C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
S C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?

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
C3 N1 C1 N2 1.1(4) . . . . ?
C027 N1 C1 N2 177.6(3) . . . . ?
C3 N1 C1 S -173.3(2) . . . . ?
C027 N1 C1 S 3.2(5) . . . . ?
C5 S C1 N1 -132.4(3) . . . . ?
C5 S C1 N2 54.3(3) . . . . ?
F1 C7 C8 F4 -179.3(3) . . . . ?
F2 C7 C8 F4 -65.5(3) . . . . ?
C6 C7 C8 F4 57.1(4) . . . . ?
F1 C7 C8 F3 65.3(3) . . . . ?
F2 C7 C8 F3 179.1(3) . . . . ?
C6 C7 C8 F3 -58.3(4) . . . . ?
F1 C7 C8 C9 -56.5(4) . . . . ?
F2 C7 C8 C9 57.3(4) . . . . ?
C6 C7 C8 C9 179.9(3) . . . . ?
F4 C8 C9 F6 59.4(3) . . . . ?
F3 C8 C9 F6 175.8(2) . . . . ?
C7 C8 C9 F6 -62.8(4) . . . . ?
F4 C8 C9 F5 177.1(2) . . . . ?
F3 C8 C9 F5 -66.4(3) . . . . ?
C7 C8 C9 F5 54.9(4) . . . . ?
F4 C8 C9 C10 -62.1(4) . . . . ?
F3 C8 C9 C10 54.3(4) . . . . ?
C7 C8 C9 C10 175.7(3) . . . . ?
F1 C7 C6 C5 52.3(4) . . . . ?
F2 C7 C6 C5 -65.2(4) . . . . ?
C8 C7 C6 C5 174.1(3) . . . . ?
F6 C9 C10 F8 -66.9(3) . . . . ?
F5 C9 C10 F8 176.4(2) . . . . ?
C8 C9 C10 F8 54.8(4) . . . . ?
F6 C9 C10 F7 175.1(2) . . . . ?
F5 C9 C10 F7 58.4(3) . . . . ?
C8 C9 C10 F7 -63.2(4) . . . . ?
F6 C9 C10 C11 54.5(4) . . . . ?
F5 C9 C10 C11 -62.3(4) . . . . ?
C8 C9 C10 C11 176.1(3) . . . . ?
N1 C1 N2 C2 -0.5(4) . . . . ?
S C1 N2 C2 173.8(2) . . . . ?
C1 N1 C3 C2 -1.2(4) . . . . ?
C027 N1 C3 C2 -177.8(3) . . . . ?
N1 C3 C2 N2 0.8(4) . . . . ?
C1 N2 C2 C3 -0.2(4) . . . . ?
F8 C10 C11 F9 -178.9(3) . . . . ?
F7 C10 C11 F9 -62.5(3) . . . . ?
C9 C10 C11 F9 59.2(4) . . . . ?
F8 C10 C11 F10 61.9(3) . . . . ?
F7 C10 C11 F10 178.3(2) . . . . ?
C9 C10 C11 F10 -60.0(4) . . . . ?
F8 C10 C11 C12 -58.7(4) . . . . ?
F7 C10 C11 C12 57.7(4) . . . . ?
C9 C10 C11 C12 179.5(3) . . . . ?
F9 C11 C12 F13 -61.2(4) . . . . ?
F10 C11 C12 F13 54.9(4) . . . . ?
C10 C11 C12 F13 177.0(3) . . . . ?
F9 C11 C12 F12 177.6(3) . . . . ?
F10 C11 C12 F12 -66.4(4) . . . . ?
C10 C11 C12 F12 55.8(4) . . . . ?
F9 C11 C12 F11 58.1(4) . . . . ?
F10 C11 C12 F11 174.2(3) . . . . ?
C10 C11 C12 F11 -63.7(4) . . . . ?
C7 C6 C5 S 176.1(3) . . . . ?
C1 S C5 C6 146.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 I 0.877(18) 2.582(19) 3.443(3) 167(3) 1_455

# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1449695'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 F13 N2 S 1+, Cl 1-'
_chemical_formula_sum            'C12 H10 Cl F13 N2 S'
_chemical_formula_weight         496.73

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3654(4)
_cell_length_b                   9.2363(5)
_cell_length_c                   16.0361(12)
_cell_angle_alpha                75.231(5)
_cell_angle_beta                 83.709(5)
_cell_angle_gamma                76.855(5)
_cell_volume                     886.44(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3049
_cell_measurement_theta_min      3.8980
_cell_measurement_theta_max      26.2210
_cell_measurement_wavelength     0.71073


_exptl_crystal_description       'platy fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.465
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.88894
_exptl_absorpt_correction_T_max  1.00000


_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.3575
_diffrn_reflns_number            13865
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3236
_reflns_number_gt                2536
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;

_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+0.6803P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3236
_refine_ls_number_parameters     276
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0816(4) 0.5989(3) 0.24943(18) 0.0269(6) Uani 1 1 d . . . . .
H1A H -0.0563 0.6069 0.2238 0.035(8) Uiso 1 1 calc R . . . .
H1B H 0.0849 0.5252 0.3064 0.029(7) Uiso 1 1 calc R . . . .
C2 C 0.0983(4) 0.7531(3) 0.26003(19) 0.0298(6) Uani 1 1 d . . . . .
C3 C -0.2557(5) 1.0662(3) 0.38168(19) 0.0314(6) Uani 1 1 d . . . . .
C4 C -0.0842(4) 0.8256(3) 0.31779(18) 0.0288(6) Uani 1 1 d . . . . .
C5 C 0.4828(4) 0.3077(3) 0.12016(17) 0.0252(6) Uani 1 1 d . . . . .
C6 C 0.2718(5) 0.5436(3) 0.19043(19) 0.0294(6) Uani 1 1 d . . . . .
H6A H 0.4098 0.5301 0.2173 0.040(8) Uiso 1 1 calc R . . . .
H6B H 0.2728 0.6193 0.1343 0.051(10) Uiso 1 1 calc R . . . .
C7 C -0.4174(6) 1.3133(4) 0.4376(2) 0.0469(8) Uani 1 1 d . . . . .
C8 C 0.7376(4) 0.1598(3) 0.05694(19) 0.0338(7) Uani 1 1 d . . . . .
H8 H 0.8153 0.0746 0.0357 0.046(9) Uiso 1 1 calc R . . . .
C9 C -0.0794(5) 0.9905(3) 0.32297(18) 0.0310(6) Uani 1 1 d . . . . .
C10 C 0.7985(5) 0.2923(3) 0.04734(19) 0.0352(7) Uani 1 1 d . . . . .
H10 H 0.9285 0.3182 0.0188 0.044(9) Uiso 1 1 calc R . . . .
C11 C -0.2483(5) 1.2339(3) 0.3790(2) 0.0379(7) Uani 1 1 d . . . . .
C12 C 0.4099(5) 0.0528(3) 0.1263(2) 0.0352(7) Uani 1 1 d . . . . .
H12A H 0.3606 0.0396 0.1873 0.033(8) Uiso 1 1 calc R . . . .
H12B H 0.4960 -0.0444 0.1166 0.042(8) Uiso 1 1 calc R . . . .
H12C H 0.2845 0.0855 0.0905 0.052(10) Uiso 1 1 calc R . . . .
N1 N 0.6380(4) 0.3850(2) 0.08644(15) 0.0283(5) Uani 1 1 d D . . . .
H1 H 0.644(5) 0.4771(17) 0.086(2) 0.044(9) Uiso 1 1 d D . . . .
N2 N 0.5420(3) 0.1690(2) 0.10310(15) 0.0267(5) Uani 1 1 d . . . . .
F1 F 0.0963(3) 0.85301(18) 0.18152(11) 0.0458(5) Uani 1 1 d . . . . .
F2 F 0.2880(3) 0.7461(2) 0.29301(14) 0.0514(5) Uani 1 1 d . . . . .
F3 F 0.1126(3) 0.9882(2) 0.35038(15) 0.0585(6) Uani 1 1 d . . . . .
F4 F -0.4492(3) 1.0658(2) 0.35659(15) 0.0570(6) Uani 1 1 d . . . . .
F5 F -0.0930(4) 1.08062(19) 0.24343(12) 0.0603(6) Uani 1 1 d . . . . .
F6 F -0.2738(3) 0.8295(2) 0.28740(14) 0.0523(5) Uani 1 1 d . . . . .
F7 F -0.2725(4) 1.31985(19) 0.29825(12) 0.0595(6) Uani 1 1 d . . . . .
F8 F -0.2364(3) 0.98498(19) 0.46297(12) 0.0539(5) Uani 1 1 d . . . . .
F9 F -0.0740(3) 0.73546(18) 0.39801(12) 0.0509(5) Uani 1 1 d . . . . .
F10 F -0.0542(3) 1.2379(2) 0.40217(16) 0.0625(6) Uani 1 1 d . . . . .
F11 F -0.4003(4) 1.2441(2) 0.51879(13) 0.0720(7) Uani 1 1 d . . . . .
F12 F -0.6144(4) 1.3193(3) 0.41693(16) 0.0753(7) Uani 1 1 d . . . . .
F13 F -0.3928(4) 1.4555(2) 0.42556(16) 0.0772(8) Uani 1 1 d . . . . .
S1 S 0.23969(12) 0.36283(8) 0.17465(6) 0.0377(2) Uani 1 1 d . . . . .
Cl1 Cl -0.27755(11) 0.69605(7) 0.08096(5) 0.0321(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.505(4) . ?
C1 C6 1.528(4) . ?
C2 F2 1.352(3) . ?
C2 F1 1.357(3) . ?
C2 C4 1.543(4) . ?
C3 F8 1.331(3) . ?
C3 F4 1.338(3) . ?
C3 C9 1.543(4) . ?
C3 C11 1.550(4) . ?
C4 F6 1.340(3) . ?
C4 F9 1.342(3) . ?
C4 C9 1.553(4) . ?
C5 N1 1.336(3) . ?
C5 N2 1.340(3) . ?
C5 S1 1.729(3) . ?
C6 S1 1.809(2) . ?
C7 F11 1.300(4) . ?
C7 F12 1.318(4) . ?
C7 F13 1.320(4) . ?
C7 C11 1.534(4) . ?
C8 C10 1.334(4) . ?
C8 N2 1.374(4) . ?
C9 F5 1.333(3) . ?
C9 F3 1.337(3) . ?
C10 N1 1.380(4) . ?
C11 F7 1.339(4) . ?
C11 F10 1.340(4) . ?
C12 N2 1.461(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
C2 C1 C6 108.6(2) . . ?
F2 C2 F1 106.1(2) . . ?
F2 C2 C1 111.1(2) . . ?
F1 C2 C1 109.6(2) . . ?
F2 C2 C4 107.4(2) . . ?
F1 C2 C4 107.1(2) . . ?
C1 C2 C4 115.0(2) . . ?
F8 C3 F4 108.6(2) . . ?
F8 C3 C9 109.4(2) . . ?
F4 C3 C9 108.5(2) . . ?
F8 C3 C11 108.3(2) . . ?
F4 C3 C11 107.8(2) . . ?
C9 C3 C11 114.1(2) . . ?
F6 C4 F9 108.3(2) . . ?
F6 C4 C2 108.2(2) . . ?
F9 C4 C2 108.4(2) . . ?
F6 C4 C9 107.9(2) . . ?
F9 C4 C9 108.3(2) . . ?
C2 C4 C9 115.4(2) . . ?
N1 C5 N2 107.8(2) . . ?
N1 C5 S1 130.46(19) . . ?
N2 C5 S1 121.74(19) . . ?
C1 C6 S1 107.54(18) . . ?
F11 C7 F12 108.0(3) . . ?
F11 C7 F13 109.7(3) . . ?
F12 C7 F13 107.5(3) . . ?
F11 C7 C11 112.4(3) . . ?
F12 C7 C11 110.8(3) . . ?
F13 C7 C11 108.3(3) . . ?
C10 C8 N2 107.5(2) . . ?
F5 C9 F3 107.2(2) . . ?
F5 C9 C3 107.8(2) . . ?
F3 C9 C3 107.7(2) . . ?
F5 C9 C4 108.4(2) . . ?
F3 C9 C4 108.2(2) . . ?
C3 C9 C4 117.3(2) . . ?
C8 C10 N1 107.5(2) . . ?
F7 C11 F10 107.5(3) . . ?
F7 C11 C7 107.1(2) . . ?
F10 C11 C7 106.8(3) . . ?
F7 C11 C3 109.9(2) . . ?
F10 C11 C3 109.1(2) . . ?
C7 C11 C3 116.1(3) . . ?
C5 N1 C10 108.5(2) . . ?
C5 N2 C8 108.7(2) . . ?
C5 N2 C12 124.3(2) . . ?
C8 N2 C12 126.9(2) . . ?
C5 S1 C6 100.55(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl1 0.859(10) 2.171(12) 3.019(2) 169(3) 1_655

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6



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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1449697'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H10 F13 N2 S 1+), Si F6 2-'
_chemical_formula_sum            'C24 H20 F32 N4 S2 Si'
_chemical_formula_weight         1064.65

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   18.463(5)
_cell_length_b                   8.901(3)
_cell_length_c                   11.595(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.185(9)
_cell_angle_gamma                90
_cell_volume                     1862.6(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3474
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      24.9

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.364
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   'Bruker DIFABS-2014/5)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microfocus'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            14436
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_av_R_equivalents  0.1063
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.257
_diffrn_reflns_theta_max         25.124
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3229
_reflns_number_gt                1900
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Apex II'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_structure_solution    'Bruker Apex II'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Only a small crystal of poor quality was available. 
 The diffraction pattern showed broad reflections and no visible
 diffraction at 2theta  angles higher than 42 deg. The N1 hydrogen atom 
 was located in a differnce map an refined with distance restraint 
 [N-H = 0.88(1) Ang].  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0955P)²+11.6698P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3229
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0902
_refine_ls_wR_factor_ref         0.2515
_refine_ls_wR_factor_gt          0.2128
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33675(13) 1.0146(2) 0.58041(16) 0.0416(6) Uani 1 1 d . . . . .
Si1 Si 0.5000 0.5000 0.5000 0.0303(7) Uani 1 2 d S . P . .
F1 F 0.2635(3) 0.6183(6) 0.7393(4) 0.0575(14) Uani 1 1 d . . . . .
F2 F 0.2002(3) 0.7766(6) 0.6155(5) 0.0567(14) Uani 1 1 d . . . . .
F3 F 0.2483(3) 0.4024(5) 0.5768(5) 0.0599(14) Uani 1 1 d . . . . .
F4 F 0.1450(3) 0.4985(6) 0.6068(5) 0.0644(15) Uani 1 1 d . . . . .
F5 F 0.2349(3) 0.5302(6) 0.3718(4) 0.0523(13) Uani 1 1 d . . . . .
F6 F 0.1459(3) 0.6776(5) 0.3997(4) 0.0559(13) Uani 1 1 d . . . . .
F7 F 0.1421(3) 0.2849(5) 0.4048(5) 0.0691(16) Uani 1 1 d . . . . .
F8 F 0.0541(3) 0.4493(6) 0.3995(5) 0.0573(14) Uani 1 1 d . . . . .
F9 F 0.1603(3) 0.3583(7) 0.1956(6) 0.083(2) Uani 1 1 d . . . . .
F10 F 0.0921(3) 0.5597(6) 0.1884(4) 0.0670(16) Uani 1 1 d . . . . .
F11 F 0.0357(4) 0.1947(8) 0.2146(7) 0.100(2) Uani 1 1 d . . . . .
F12 F -0.0278(3) 0.3959(8) 0.1843(6) 0.084(2) Uani 1 1 d . . . . .
F13 F 0.0305(4) 0.3184(9) 0.0565(6) 0.098(2) Uani 1 1 d . . . . .
F14 F 0.4227(3) 0.5510(5) 0.4068(4) 0.0445(12) Uani 1 1 d . . . . .
F15 F 0.5482(3) 0.6199(4) 0.4338(3) 0.0417(12) Uani 1 1 d . . . . .
F16 F 0.4859(3) 0.6409(4) 0.5924(3) 0.0384(11) Uani 1 1 d . . . . .
C1 C 0.3853(4) 0.9925(7) 0.4694(6) 0.0314(17) Uani 1 1 d . . . . .
C2 C 0.4566(4) 0.9129(8) 0.3503(6) 0.0347(18) Uani 1 1 d . . . . .
H2 H 0.4895 0.8525 0.3173 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4260(4) 1.0432(8) 0.3074(6) 0.0352(18) Uani 1 1 d . . . . .
H3 H 0.4339 1.0930 0.2386 0.042 Uiso 1 1 calc R U . . .
C4 C 0.3335(5) 1.2272(8) 0.3627(7) 0.044(2) Uani 1 1 d . . . . .
H4A H 0.2820 1.1987 0.3603 0.066 Uiso 1 1 calc R U . . .
H4B H 0.3371 1.2745 0.2878 0.066 Uiso 1 1 calc R U . . .
H4C H 0.3501 1.2982 0.4274 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3558(5) 0.8361(8) 0.6527(7) 0.040(2) Uani 1 1 d . . . . .
H5A H 0.4099 0.8185 0.6686 0.048 Uiso 1 1 calc R U . . .
H5B H 0.3408 0.8409 0.7297 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3169(4) 0.7020(8) 0.5834(7) 0.0369(18) Uani 1 1 d . . . . .
H6A H 0.3051 0.7269 0.4983 0.044 Uiso 1 1 calc R U . . .
H6B H 0.3509 0.6147 0.5947 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2467(5) 0.6602(10) 0.6218(7) 0.043(2) Uani 1 1 d . . . . .
C8 C 0.2038(5) 0.5238(9) 0.5590(7) 0.042(2) Uani 1 1 d . . . . .
C9 C 0.1754(5) 0.5396(9) 0.4231(7) 0.041(2) Uani 1 1 d . . . . .
C10 C 0.1173(5) 0.4227(9) 0.3675(8) 0.045(2) Uani 1 1 d . . . . .
C11 C 0.1011(5) 0.4158(11) 0.2290(8) 0.053(2) Uani 1 1 d . . . . .
C12 C 0.0337(6) 0.3335(13) 0.1705(10) 0.066(3) Uani 1 1 d . . . . .
N1 N 0.4312(4) 0.8830(6) 0.4523(5) 0.0303(14) Uani 1 1 d D . . . .
H1 H 0.450(4) 0.813(6) 0.500(5) 0.036 Uiso 1 1 d D U . . .
N2 N 0.3805(4) 1.0925(6) 0.3815(5) 0.0361(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.728(7) . ?
S1 C5 1.796(8) . ?
Si1 F14 1.661(5) 3_666 ?
Si1 F14 1.661(5) . ?
Si1 F15 1.675(4) . ?
Si1 F15 1.676(4) 3_666 ?
Si1 F16 1.705(4) 3_666 ?
Si1 F16 1.705(4) . ?
F1 C7 1.383(9) . ?
F2 C7 1.338(9) . ?
F3 C8 1.347(9) . ?
F4 C8 1.338(9) . ?
F5 C9 1.357(9) . ?
F6 C9 1.348(9) . ?
F7 C10 1.348(10) . ?
F8 C10 1.318(9) . ?
F9 C11 1.338(10) . ?
F10 C11 1.362(11) . ?
F11 C12 1.335(12) . ?
F12 C12 1.304(12) . ?
F13 C12 1.318(12) . ?
C1 N1 1.334(9) . ?
C1 N2 1.342(9) . ?
C2 C3 1.340(11) . ?
C2 N1 1.387(9) . ?
C2 H2 0.9500 . ?
C3 N2 1.393(9) . ?
C3 H3 0.9500 . ?
C4 N2 1.469(9) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.530(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.502(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.546(12) . ?
C8 C9 1.558(12) . ?
C9 C10 1.536(12) . ?
C10 C11 1.572(13) . ?
C11 C12 1.479(14) . ?
N1 H1 0.858(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C5 99.6(3) . . ?
F14 Si1 F14 180.0(2) 3_666 . ?
F14 Si1 F15 90.3(2) 3_666 . ?
F14 Si1 F15 89.7(2) . . ?
F14 Si1 F15 89.7(2) 3_666 3_666 ?
F14 Si1 F15 90.3(2) . 3_666 ?
F15 Si1 F15 180.0 . 3_666 ?
F14 Si1 F16 89.1(2) 3_666 3_666 ?
F14 Si1 F16 90.9(2) . 3_666 ?
F15 Si1 F16 90.82(19) . 3_666 ?
F15 Si1 F16 89.18(19) 3_666 3_666 ?
F14 Si1 F16 90.9(2) 3_666 . ?
F14 Si1 F16 89.1(2) . . ?
F15 Si1 F16 89.18(19) . . ?
F15 Si1 F16 90.82(19) 3_666 . ?
F16 Si1 F16 180.0 3_666 . ?
N1 C1 N2 108.3(6) . . ?
N1 C1 S1 129.7(5) . . ?
N2 C1 S1 122.0(5) . . ?
C3 C2 N1 106.9(6) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 107.8(6) . . ?
C2 C3 H3 126.1 . . ?
N2 C3 H3 126.1 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S1 114.9(6) . . ?
C6 C5 H5A 108.5 . . ?
S1 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
S1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C7 C6 C5 112.1(6) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
F2 C7 F1 105.6(6) . . ?
F2 C7 C6 112.1(7) . . ?
F1 C7 C6 109.3(7) . . ?
F2 C7 C8 108.8(7) . . ?
F1 C7 C8 103.8(7) . . ?
C6 C7 C8 116.4(7) . . ?
F4 C8 F3 108.8(6) . . ?
F4 C8 C7 108.5(7) . . ?
F3 C8 C7 108.8(7) . . ?
F4 C8 C9 107.8(7) . . ?
F3 C8 C9 106.9(6) . . ?
C7 C8 C9 115.8(7) . . ?
F6 C9 F5 107.3(6) . . ?
F6 C9 C10 108.4(7) . . ?
F5 C9 C10 109.4(6) . . ?
F6 C9 C8 108.7(6) . . ?
F5 C9 C8 107.9(7) . . ?
C10 C9 C8 114.8(7) . . ?
F8 C10 F7 109.6(7) . . ?
F8 C10 C9 110.0(7) . . ?
F7 C10 C9 108.7(7) . . ?
F8 C10 C11 107.8(7) . . ?
F7 C10 C11 105.7(7) . . ?
C9 C10 C11 114.9(7) . . ?
F9 C11 F10 107.8(7) . . ?
F9 C11 C12 109.7(8) . . ?
F10 C11 C12 106.2(8) . . ?
F9 C11 C10 108.7(8) . . ?
F10 C11 C10 107.4(7) . . ?
C12 C11 C10 116.6(8) . . ?
F12 C12 F13 108.1(10) . . ?
F12 C12 F11 107.6(9) . . ?
F13 C12 F11 106.4(9) . . ?
F12 C12 C11 113.7(9) . . ?
F13 C12 C11 111.4(9) . . ?
F11 C12 C11 109.3(9) . . ?
C1 N1 C2 109.1(6) . . ?
C1 N1 H1 128(5) . . ?
C2 N1 H1 122(5) . . ?
C1 N2 C3 107.9(6) . . ?
C1 N2 C4 126.6(6) . . ?
C3 N2 C4 125.4(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
C5 S1 C1 N1 -7.7(8) . . . . ?
C5 S1 C1 N2 171.9(7) . . . . ?
N1 C2 C3 N2 -1.1(9) . . . . ?
C1 S1 C5 C6 -71.1(6) . . . . ?
S1 C5 C6 C7 -97.0(7) . . . . ?
C5 C6 C7 F2 55.0(9) . . . . ?
C5 C6 C7 F1 -61.8(9) . . . . ?
C5 C6 C7 C8 -178.8(7) . . . . ?
F2 C7 C8 F4 -54.8(8) . . . . ?
F1 C7 C8 F4 57.3(8) . . . . ?
C6 C7 C8 F4 177.4(7) . . . . ?
F2 C7 C8 F3 -173.0(6) . . . . ?
F1 C7 C8 F3 -60.9(7) . . . . ?
C6 C7 C8 F3 59.2(9) . . . . ?
F2 C7 C8 C9 66.5(8) . . . . ?
F1 C7 C8 C9 178.6(6) . . . . ?
C6 C7 C8 C9 -61.3(10) . . . . ?
F4 C8 C9 F6 77.8(8) . . . . ?
F3 C8 C9 F6 -165.3(6) . . . . ?
C7 C8 C9 F6 -43.9(9) . . . . ?
F4 C8 C9 F5 -166.0(6) . . . . ?
F3 C8 C9 F5 -49.2(8) . . . . ?
C7 C8 C9 F5 72.3(8) . . . . ?
F4 C8 C9 C10 -43.7(9) . . . . ?
F3 C8 C9 C10 73.1(8) . . . . ?
C7 C8 C9 C10 -165.4(7) . . . . ?
F6 C9 C10 F8 -51.1(9) . . . . ?
F5 C9 C10 F8 -167.9(6) . . . . ?
C8 C9 C10 F8 70.6(9) . . . . ?
F6 C9 C10 F7 -171.1(6) . . . . ?
F5 C9 C10 F7 72.1(8) . . . . ?
C8 C9 C10 F7 -49.4(9) . . . . ?
F6 C9 C10 C11 70.7(9) . . . . ?
F5 C9 C10 C11 -46.1(9) . . . . ?
C8 C9 C10 C11 -167.6(7) . . . . ?
F8 C10 C11 F9 -167.1(7) . . . . ?
F7 C10 C11 F9 -50.0(9) . . . . ?
C9 C10 C11 F9 69.8(9) . . . . ?
F8 C10 C11 F10 76.4(8) . . . . ?
F7 C10 C11 F10 -166.5(7) . . . . ?
C9 C10 C11 F10 -46.6(10) . . . . ?
F8 C10 C11 C12 -42.5(11) . . . . ?
F7 C10 C11 C12 74.6(10) . . . . ?
C9 C10 C11 C12 -165.5(8) . . . . ?
F9 C11 C12 F12 -170.4(8) . . . . ?
F10 C11 C12 F12 -54.1(11) . . . . ?
C10 C11 C12 F12 65.5(12) . . . . ?
F9 C11 C12 F13 -47.9(12) . . . . ?
F10 C11 C12 F13 68.4(11) . . . . ?
C10 C11 C12 F13 -172.0(9) . . . . ?
F9 C11 C12 F11 69.3(11) . . . . ?
F10 C11 C12 F11 -174.4(8) . . . . ?
C10 C11 C12 F11 -54.7(12) . . . . ?
N2 C1 N1 C2 -0.2(9) . . . . ?
S1 C1 N1 C2 179.5(6) . . . . ?
C3 C2 N1 C1 0.8(9) . . . . ?
N1 C1 N2 C3 -0.5(8) . . . . ?
S1 C1 N2 C3 179.8(5) . . . . ?
N1 C1 N2 C4 177.1(7) . . . . ?
S1 C1 N2 C4 -2.6(11) . . . . ?
C2 C3 N2 C1 1.0(9) . . . . ?
C2 C3 N2 C4 -176.6(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 F16 0.858(10) 1.905(16) 2.759(7) 173(8) .

_refine_diff_density_max         0.928
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.108

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_gp138_2
_database_code_depnum_ccdc_archive 'CCDC 1449696'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_date             2015-04-14T16:48:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C20 H10 F30 I2 N2 S'
_chemical_formula_moiety         'C12 H10 F13 N2 S 1+, C8 F17 I, I 1-'

_chemical_formula_weight         1134.16

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4954(5)
_cell_length_b                   9.2039(8)
_cell_length_c                   27.9195(19)
_cell_angle_alpha                94.848(6)
_cell_angle_beta                 91.767(6)
_cell_angle_gamma                95.367(7)
_cell_volume                     1654.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2687
_cell_measurement_theta_min      3.166
_cell_measurement_theta_max      26.963

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

_exptl_crystal_description       'platy fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    2.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.022
0 0 1 0.047
0 1 -5 0.0317
-2 4 5 0.0947
2 -5 -1 0.1213
3 1 5 0.1318
1 2 5 0.0939
-3 -5 2 0.0991
0 -4 -5 0.0534
0 -2 5 0.082
-5 1 2 0.1094
-1 0 -5 0.0418
2 -6 35 0.0761
1 7 30 0.0836

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  0.877

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

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3575
_diffrn_orient_matrix_ub_11      0.0710431
_diffrn_orient_matrix_ub_12      -0.0530909
_diffrn_orient_matrix_ub_13      0.0026032
_diffrn_orient_matrix_ub_21      -0.0793951
_diffrn_orient_matrix_ub_22      -0.0566128
_diffrn_orient_matrix_ub_23      -0.0071502
_diffrn_orient_matrix_ub_31      0.0264129
_diffrn_orient_matrix_ub_32      0.0037957
_diffrn_orient_matrix_ub_33      -0.0243548
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_number            9260
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             5964
_reflns_number_gt                4502
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2015)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5961
_refine_ls_number_parameters     592
_refine_ls_number_restraints     448
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I 0.20124(6) 0.24421(4) 0.94366(2) 0.03572(14) Uani 1 1 d . . . . .
S1 S 0.7747(3) 0.9102(2) 0.91141(7) 0.0538(5) Uani 1 1 d . . . . .
N1 N 0.5042(7) 0.6954(6) 0.94026(15) 0.0311(11) Uani 1 1 d . . . . .
N2 N 0.3905(8) 0.9070(6) 0.95087(17) 0.0353(12) Uani 1 1 d D . . . .
H2 H 0.366(9) 1.000(3) 0.947(2) 0.042 Uiso 1 1 d D U . . .
C1 C 0.5450(9) 0.8375(7) 0.93342(19) 0.0331(14) Uani 1 1 d . . . . .
C2 C 0.3215(9) 0.6775(7) 0.9629(2) 0.0353(15) Uani 1 1 d . . . . .
H2A H 0.2574 0.5880 0.9724 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2492(9) 0.8088(7) 0.96943(19) 0.0343(15) Uani 1 1 d . . . . .
H3 H 0.1240 0.8300 0.9841 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6354(10) 0.5817(8) 0.9255(2) 0.0451(17) Uani 1 1 d . . . . .
H4A H 0.6697 0.5886 0.8918 0.068 Uiso 1 1 calc R U . . .
H4C H 0.5621 0.4854 0.9290 0.068 Uiso 1 1 calc R U . . .
H4B H 0.7630 0.5942 0.9457 0.068 Uiso 1 1 calc R U . . .
C5 C 0.6953(9) 1.0582(8) 0.8789(2) 0.0399(16) Uani 1 1 d . . . . .
H5A H 0.6226 1.1246 0.9008 0.048 Uiso 1 1 calc R U . . .
H5B H 0.8198 1.1151 0.8682 0.048 Uiso 1 1 calc R U . . .
C6 C 0.5528(10) 1.0043(7) 0.8350(2) 0.0392(16) Uani 1 1 d . . . . .
H6A H 0.6007 0.9139 0.8191 0.047 Uiso 1 1 calc R U . . .
H6B H 0.4105 0.9802 0.8456 0.047 Uiso 1 1 calc R U . . .
C7 C 0.5507(8) 1.1193(7) 0.79951(18) 0.0320(14) Uani 1 1 d D . . . .
F7A F 0.5149(6) 1.2499(4) 0.82176(12) 0.0536(10) Uani 1 1 d . . . . .
F7B F 0.7383(5) 1.1398(5) 0.78068(12) 0.0557(12) Uani 1 1 d . . . . .
C8 C 0.3879(9) 1.0813(6) 0.75795(17) 0.0312(14) Uani 1 1 d D . . . .
F8A F 0.4144(7) 0.9452(5) 0.73941(13) 0.0637(12) Uani 1 1 d . . . . .
F8B F 0.2015(5) 1.0764(5) 0.77738(13) 0.0622(13) Uani 1 1 d . . . . .
C9 C 0.3899(8) 1.1840(7) 0.71715(18) 0.0338(14) Uani 1 1 d D . . . .
F9A F 0.3843(6) 1.3205(4) 0.73610(12) 0.0534(10) Uani 1 1 d . . . . .
F9B F 0.5704(5) 1.1745(5) 0.69534(12) 0.0569(12) Uani 1 1 d . . . . .
C10 C 0.2133(8) 1.1493(6) 0.67864(17) 0.0315(14) Uani 1 1 d D . . . .
F10A F 0.0324(5) 1.1634(5) 0.69939(12) 0.0474(10) Uani 1 1 d . . . . .
F10B F 0.2127(7) 1.0091(4) 0.66077(13) 0.0564(11) Uani 1 1 d . . . . .
C11 C 0.219(5) 1.250(3) 0.6370(9) 0.041(2) Uani 0.55 1 d D . P A 1
F11A F 0.197(7) 1.385(4) 0.6574(12) 0.062(6) Uani 0.55 1 d D . P A 1
F11B F 0.398(4) 1.255(5) 0.6150(17) 0.069(7) Uani 0.55 1 d D . P A 1
C12 C 0.045(4) 1.216(2) 0.5978(8) 0.0466(18) Uani 0.55 1 d D . P A 1
F12A F 0.052(4) 1.324(3) 0.5689(6) 0.063(5) Uani 0.55 1 d D . P A 1
F12B F -0.139(5) 1.202(3) 0.6167(11) 0.071(6) Uani 0.55 1 d D . P A 1
F12C F 0.072(5) 1.093(2) 0.5712(10) 0.083(6) Uani 0.55 1 d D . P A 1
C11' C 0.226(6) 1.245(4) 0.6358(11) 0.041(2) Uani 0.45 1 d D . P A 2
F11C F 0.236(9) 1.388(5) 0.6506(16) 0.062(6) Uani 0.45 1 d D . P A 2
F11D F 0.399(6) 1.219(7) 0.614(2) 0.069(7) Uani 0.45 1 d D . P A 2
C12' C 0.046(5) 1.215(3) 0.5982(9) 0.0466(18) Uani 0.45 1 d D . P A 2
F12D F 0.090(5) 1.291(3) 0.5605(8) 0.063(5) Uani 0.45 1 d D . P A 2
F12E F -0.128(6) 1.255(4) 0.6163(14) 0.071(6) Uani 0.45 1 d D . P A 2
F12F F 0.019(7) 1.074(3) 0.5827(14) 0.083(6) Uani 0.45 1 d D . P A 2
I1 I 0.10482(6) 0.47030(5) 0.84905(2) 0.03811(14) Uani 1 1 d . . . . .
C13 C 0.0824(9) 0.6300(7) 0.7973(2) 0.0393(15) Uani 1 1 d D . . . .
F13A F 0.0489(8) 0.7589(5) 0.81952(13) 0.0753(14) Uani 1 1 d . . . . .
F13B F 0.2660(6) 0.6484(6) 0.77669(14) 0.0732(15) Uani 1 1 d . . . . .
C14 C -0.0876(8) 0.5827(6) 0.75799(17) 0.0317(14) Uani 1 1 d D . . . .
F14A F -0.2677(6) 0.5756(5) 0.77971(13) 0.0625(13) Uani 1 1 d . . . . .
F14B F -0.0582(7) 0.4497(4) 0.73916(12) 0.0578(11) Uani 1 1 d . . . . .
C15 C -0.1015(9) 0.6860(7) 0.71725(18) 0.0338(14) Uani 1 1 d D . . . .
F15A F 0.0789(6) 0.6925(5) 0.69528(12) 0.0584(12) Uani 1 1 d . . . . .
F15B F -0.1276(7) 0.8200(5) 0.73671(13) 0.0614(12) Uani 1 1 d . . . . .
C16 C -0.2750(9) 0.6398(6) 0.67845(17) 0.0368(15) Uani 1 1 d D . . . .
F16A F -0.4574(6) 0.6513(6) 0.69931(13) 0.0663(14) Uani 1 1 d . . . . .
F16B F -0.2702(8) 0.4990(5) 0.66365(14) 0.0724(14) Uani 1 1 d . . . . .
C17 C -0.2692(17) 0.7229(10) 0.6330(3) 0.044(2) Uani 0.6 1 d D . P B 1
F17A F -0.1099(18) 0.6798(18) 0.6074(4) 0.083(5) Uani 0.6 1 d D U P B 1
F17B F -0.229(3) 0.8661(9) 0.6462(5) 0.077(5) Uani 0.6 1 d D U P B 1
C18 C -0.4630(15) 0.6986(10) 0.5993(3) 0.0432(17) Uani 0.6 1 d D . P B 1
F18A F -0.5285(15) 0.5553(9) 0.5950(3) 0.066(3) Uani 0.6 1 d D U P B 1
F18B F -0.6143(19) 0.7677(13) 0.6208(4) 0.087(4) Uani 0.6 1 d D U P B 1
C19 C -0.4402(14) 0.7510(10) 0.5490(3) 0.054(3) Uani 0.6 1 d D . P B 1
F19A F -0.3447(19) 0.8855(10) 0.5531(4) 0.089(4) Uani 0.6 1 d D U P B 1
F19B F -0.3304(15) 0.6601(12) 0.5235(3) 0.090(4) Uani 0.6 1 d D U P B 1
C20 C -0.6421(14) 0.7576(10) 0.5199(3) 0.062(2) Uani 0.6 1 d D . P B 1
F20A F -0.6008(17) 0.7812(13) 0.4753(3) 0.076(3) Uani 0.6 1 d D U P B 1
F20B F -0.7537(15) 0.6307(10) 0.5184(3) 0.075(3) Uani 0.6 1 d D U P B 1
F20C F -0.7500(18) 0.8621(12) 0.5377(3) 0.105(4) Uani 0.6 1 d D U P B 1
C17' C -0.279(2) 0.7387(15) 0.6369(4) 0.044(2) Uani 0.4 1 d D . P B 2
F17C F -0.099(3) 0.736(3) 0.6147(6) 0.083(5) Uani 0.4 1 d D . P B 2
F17D F -0.291(4) 0.8768(13) 0.6550(8) 0.077(5) Uani 0.4 1 d D . P B 2
C18' C -0.454(2) 0.6985(14) 0.5985(4) 0.0432(17) Uani 0.4 1 d D . P B 2
F18C F -0.445(2) 0.5606(13) 0.5801(5) 0.066(3) Uani 0.4 1 d D . P B 2
F18D F -0.636(3) 0.702(2) 0.6203(7) 0.087(4) Uani 0.4 1 d D . P B 2
C19' C -0.4584(18) 0.7964(12) 0.5568(4) 0.054(3) Uani 0.4 1 d D . P B 2
F19C F -0.481(3) 0.9311(13) 0.5751(5) 0.106(6) Uani 0.4 1 d D . P B 2
F19D F -0.280(2) 0.794(3) 0.5354(6) 0.126(11) Uani 0.4 1 d D . P B 2
C20' C -0.6295(19) 0.7534(14) 0.5181(4) 0.062(2) Uani 0.4 1 d D . P B 2
F20D F -0.633(3) 0.8510(16) 0.4865(5) 0.089(6) Uani 0.4 1 d D U P B 2
F20E F -0.599(4) 0.6272(17) 0.4950(6) 0.158(8) Uani 0.4 1 d D U P B 2
F20F F -0.814(2) 0.741(3) 0.5364(6) 0.126(7) Uani 0.4 1 d D U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.729(6) . ?
S1 C5 1.805(6) . ?
N1 C1 1.341(8) . ?
N1 C2 1.365(7) . ?
N1 C4 1.452(7) . ?
N2 C1 1.323(8) . ?
N2 C3 1.372(8) . ?
N2 H2 0.90(2) . ?
C2 C3 1.337(8) . ?
C2 H2A 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4C 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.531(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.511(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 F7B 1.345(6) . ?
C7 F7A 1.349(7) . ?
C7 C8 1.541(6) . ?
C8 F8B 1.340(6) . ?
C8 F8A 1.342(7) . ?
C8 C9 1.540(6) . ?
C9 F9A 1.326(7) . ?
C9 F9B 1.345(6) . ?
C9 C10 1.539(6) . ?
C10 F10A 1.338(6) . ?
C10 F10B 1.343(7) . ?
C10 C11' 1.542(7) . ?
C10 C11 1.544(7) . ?
C11 F11B 1.333(7) . ?
C11 F11A 1.348(7) . ?
C11 C12 1.536(7) . ?
C12 F12B 1.323(7) . ?
C12 F12C 1.329(7) . ?
C12 F12A 1.331(7) . ?
C11' F11D 1.332(7) . ?
C11' F11C 1.346(7) . ?
C11' C12' 1.536(7) . ?
C12' F12E 1.324(7) . ?
C12' F12F 1.329(7) . ?
C12' F12D 1.332(7) . ?
I1 C13 2.157(6) . ?
C13 F13A 1.331(7) . ?
C13 F13B 1.343(7) . ?
C13 C14 1.539(6) . ?
C14 F14B 1.324(7) . ?
C14 F14A 1.333(6) . ?
C14 C15 1.548(6) . ?
C15 F15B 1.333(7) . ?
C15 F15A 1.338(6) . ?
C15 C16 1.543(6) . ?
C16 F16B 1.330(7) . ?
C16 F16A 1.345(6) . ?
C16 C17' 1.536(7) . ?
C16 C17 1.537(6) . ?
C17 F17B 1.338(7) . ?
C17 F17A 1.346(6) . ?
C17 C18 1.535(6) . ?
C18 F18A 1.342(6) . ?
C18 F18B 1.349(6) . ?
C18 C19 1.530(6) . ?
C19 F19A 1.326(7) . ?
C19 F19B 1.327(7) . ?
C19 C20 1.531(7) . ?
C20 F20B 1.313(7) . ?
C20 F20A 1.314(7) . ?
C20 F20C 1.315(7) . ?
C17' F17D 1.337(7) . ?
C17' F17C 1.344(7) . ?
C17' C18' 1.534(7) . ?
C18' F18C 1.335(7) . ?
C18' F18D 1.346(7) . ?
C18' C19' 1.532(7) . ?
C19' F19C 1.324(7) . ?
C19' F19D 1.324(7) . ?
C19' C20' 1.526(7) . ?
C20' F20D 1.314(7) . ?
C20' F20F 1.315(8) . ?
C20' F20E 1.315(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C5 102.9(3) . . ?
C1 N1 C2 108.7(5) . . ?
C1 N1 C4 124.6(5) . . ?
C2 N1 C4 126.7(5) . . ?
C1 N2 C3 109.4(5) . . ?
C1 N2 H2 127(4) . . ?
C3 N2 H2 123(4) . . ?
N2 C1 N1 107.4(5) . . ?
N2 C1 S1 128.7(5) . . ?
N1 C1 S1 123.5(5) . . ?
C3 C2 N1 107.7(5) . . ?
C3 C2 H2A 126.2 . . ?
N1 C2 H2A 126.2 . . ?
C2 C3 N2 106.8(5) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4C C4 H4B 109.5 . . ?
C6 C5 S1 112.7(5) . . ?
C6 C5 H5A 109.1 . . ?
S1 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
S1 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 111.1(5) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
F7B C7 F7A 106.0(5) . . ?
F7B C7 C6 109.7(5) . . ?
F7A C7 C6 110.8(5) . . ?
F7B C7 C8 108.5(4) . . ?
F7A C7 C8 107.8(5) . . ?
C6 C7 C8 113.8(5) . . ?
F8B C8 F8A 107.5(5) . . ?
F8B C8 C9 108.6(5) . . ?
F8A C8 C9 109.2(4) . . ?
F8B C8 C7 107.1(4) . . ?
F8A C8 C7 106.6(5) . . ?
C9 C8 C7 117.4(5) . . ?
F9A C9 F9B 108.4(5) . . ?
F9A C9 C10 108.5(5) . . ?
F9B C9 C10 108.1(4) . . ?
F9A C9 C8 109.0(4) . . ?
F9B C9 C8 107.0(5) . . ?
C10 C9 C8 115.6(5) . . ?
F10A C10 F10B 107.6(5) . . ?
F10A C10 C9 109.0(4) . . ?
F10B C10 C9 108.8(5) . . ?
F10A C10 C11' 108.4(19) . . ?
F10B C10 C11' 107.4(19) . . ?
C9 C10 C11' 115.4(15) . . ?
F10A C10 C11 105.9(15) . . ?
F10B C10 C11 109.6(15) . . ?
C9 C10 C11 115.6(13) . . ?
F11B C11 F11A 107.8(9) . . ?
F11B C11 C12 107.3(8) . . ?
F11A C11 C12 106.2(8) . . ?
F11B C11 C10 113(3) . . ?
F11A C11 C10 106(3) . . ?
C12 C11 C10 116.7(16) . . ?
F12B C12 F12C 108.8(9) . . ?
F12B C12 F12A 109.1(8) . . ?
F12C C12 F12A 107.8(8) . . ?
F12B C12 C11 111.4(8) . . ?
F12C C12 C11 110.3(8) . . ?
F12A C12 C11 109.5(8) . . ?
F11D C11' F11C 108.7(11) . . ?
F11D C11' C12' 107.7(10) . . ?
F11C C11' C12' 106.3(10) . . ?
F11D C11' C10 107(4) . . ?
F11C C11' C10 112(4) . . ?
C12' C11' C10 115.9(19) . . ?
F12E C12' F12F 108.7(10) . . ?
F12E C12' F12D 109.0(9) . . ?
F12F C12' F12D 108.0(9) . . ?
F12E C12' C11' 111.0(9) . . ?
F12F C12' C11' 110.7(9) . . ?
F12D C12' C11' 109.4(10) . . ?
F13A C13 F13B 107.0(6) . . ?
F13A C13 C14 109.9(5) . . ?
F13B C13 C14 109.1(5) . . ?
F13A C13 I1 110.1(4) . . ?
F13B C13 I1 107.8(4) . . ?
C14 C13 I1 112.7(4) . . ?
F14B C14 F14A 108.4(5) . . ?
F14B C14 C13 108.2(5) . . ?
F14A C14 C13 106.9(4) . . ?
F14B C14 C15 109.4(4) . . ?
F14A C14 C15 108.0(4) . . ?
C13 C14 C15 115.7(5) . . ?
F15B C15 F15A 108.1(5) . . ?
F15B C15 C16 108.5(5) . . ?
F15A C15 C16 107.7(4) . . ?
F15B C15 C14 108.8(4) . . ?
F15A C15 C14 108.0(4) . . ?
C16 C15 C14 115.6(5) . . ?
F16B C16 F16A 106.4(5) . . ?
F16B C16 C17' 113.1(7) . . ?
F16A C16 C17' 104.6(7) . . ?
F16B C16 C17 106.3(5) . . ?
F16A C16 C17 109.6(6) . . ?
F16B C16 C15 109.4(5) . . ?
F16A C16 C15 107.8(4) . . ?
C17' C16 C15 114.9(7) . . ?
C17 C16 C15 116.9(6) . . ?
F17B C17 F17A 107.8(8) . . ?
F17B C17 C18 109.2(7) . . ?
F17A C17 C18 107.2(7) . . ?
F17B C17 C16 108.5(7) . . ?
F17A C17 C16 107.2(7) . . ?
C18 C17 C16 116.5(7) . . ?
F18A C18 F18B 106.4(8) . . ?
F18A C18 C19 108.8(6) . . ?
F18B C18 C19 108.1(7) . . ?
F18A C18 C17 108.6(6) . . ?
F18B C18 C17 108.1(7) . . ?
C19 C18 C17 116.5(6) . . ?
F19A C19 F19B 110.4(9) . . ?
F19A C19 C18 108.8(7) . . ?
F19B C19 C18 108.6(7) . . ?
F19A C19 C20 106.5(7) . . ?
F19B C19 C20 106.5(7) . . ?
C18 C19 C20 115.9(6) . . ?
F20B C20 F20A 107.0(8) . . ?
F20B C20 F20C 109.8(9) . . ?
F20A C20 F20C 108.5(8) . . ?
F20B C20 C19 109.5(7) . . ?
F20A C20 C19 109.7(7) . . ?
F20C C20 C19 112.2(8) . . ?
F17D C17' F17C 106.9(10) . . ?
F17D C17' C18' 108.5(9) . . ?
F17C C17' C18' 107.7(9) . . ?
F17D C17' C16 108.9(9) . . ?
F17C C17' C16 108.4(9) . . ?
C18' C17' C16 116.2(8) . . ?
F18C C18' F18D 106.8(10) . . ?
F18C C18' C19' 108.3(8) . . ?
F18D C18' C19' 107.8(9) . . ?
F18C C18' C17' 109.2(8) . . ?
F18D C18' C17' 108.1(8) . . ?
C19' C18' C17' 116.3(8) . . ?
F19C C19' F19D 109.7(11) . . ?
F19C C19' C20' 107.7(9) . . ?
F19D C19' C20' 107.3(10) . . ?
F19C C19' C18' 107.8(9) . . ?
F19D C19' C18' 108.2(9) . . ?
C20' C19' C18' 116.0(8) . . ?
F20D C20' F20F 107.1(10) . . ?
F20D C20' F20E 107.8(10) . . ?
F20F C20' F20E 108.4(11) . . ?
F20D C20' C19' 111.5(10) . . ?
F20F C20' C19' 112.1(10) . . ?
F20E C20' C19' 109.8(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
C3 N2 C1 N1 0.3(7) . . . . ?
C3 N2 C1 S1 -173.0(4) . . . . ?
C2 N1 C1 N2 -0.7(7) . . . . ?
C4 N1 C1 N2 179.2(5) . . . . ?
C2 N1 C1 S1 173.1(4) . . . . ?
C4 N1 C1 S1 -7.0(8) . . . . ?
C5 S1 C1 N2 -39.1(6) . . . . ?
C5 S1 C1 N1 148.5(5) . . . . ?
C1 N1 C2 C3 0.8(7) . . . . ?
C4 N1 C2 C3 -179.1(6) . . . . ?
N1 C2 C3 N2 -0.5(7) . . . . ?
C1 N2 C3 C2 0.1(7) . . . . ?
C1 S1 C5 C6 -65.7(5) . . . . ?
S1 C5 C6 C7 -159.8(4) . . . . ?
C5 C6 C7 F7B 66.4(7) . . . . ?
C5 C6 C7 F7A -50.3(7) . . . . ?
C5 C6 C7 C8 -171.9(5) . . . . ?
F7B C7 C8 F8B -173.8(5) . . . . ?
F7A C7 C8 F8B -59.4(6) . . . . ?
C6 C7 C8 F8B 63.9(7) . . . . ?
F7B C7 C8 F8A 71.4(6) . . . . ?
F7A C7 C8 F8A -174.2(4) . . . . ?
C6 C7 C8 F8A -51.0(6) . . . . ?
F7B C7 C8 C9 -51.3(7) . . . . ?
F7A C7 C8 C9 63.1(6) . . . . ?
C6 C7 C8 C9 -173.7(5) . . . . ?
F8B C8 C9 F9A 69.2(6) . . . . ?
F8A C8 C9 F9A -173.9(5) . . . . ?
C7 C8 C9 F9A -52.5(7) . . . . ?
F8B C8 C9 F9B -173.8(5) . . . . ?
F8A C8 C9 F9B -56.8(6) . . . . ?
C7 C8 C9 F9B 64.5(7) . . . . ?
F8B C8 C9 C10 -53.3(7) . . . . ?
F8A C8 C9 C10 63.6(6) . . . . ?
C7 C8 C9 C10 -175.0(5) . . . . ?
F9A C9 C10 F10A -60.3(6) . . . . ?
F9B C9 C10 F10A -177.7(5) . . . . ?
C8 C9 C10 F10A 62.4(7) . . . . ?
F9A C9 C10 F10B -177.4(4) . . . . ?
F9B C9 C10 F10B 65.2(6) . . . . ?
C8 C9 C10 F10B -54.6(6) . . . . ?
F9A C9 C10 C11' 62(2) . . . . ?
F9B C9 C10 C11' -56(2) . . . . ?
C8 C9 C10 C11' -175(2) . . . . ?
F9A C9 C10 C11 58.8(19) . . . . ?
F9B C9 C10 C11 -58.6(19) . . . . ?
C8 C9 C10 C11 -178.4(18) . . . . ?
F10A C10 C11 F11B 175.5(14) . . . . ?
F10B C10 C11 F11B -68.7(16) . . . . ?
C9 C10 C11 F11B 54.7(16) . . . . ?
F10A C10 C11 F11A 58.0(17) . . . . ?
F10B C10 C11 F11A 173.8(14) . . . . ?
C9 C10 C11 F11A -62.8(16) . . . . ?
F10A C10 C11 C12 -60(3) . . . . ?
F10B C10 C11 C12 56(3) . . . . ?
C9 C10 C11 C12 179.4(16) . . . . ?
F11B C11 C12 F12B 177(2) . . . . ?
F11A C11 C12 F12B -68(2) . . . . ?
C10 C11 C12 F12B 50(3) . . . . ?
F11B C11 C12 F12C 56(2) . . . . ?
F11A C11 C12 F12C 171(2) . . . . ?
C10 C11 C12 F12C -71(2) . . . . ?
F11B C11 C12 F12A -62(2) . . . . ?
F11A C11 C12 F12A 53(2) . . . . ?
C10 C11 C12 F12A 170(2) . . . . ?
F10A C10 C11' F11D -175.0(18) . . . . ?
F10B C10 C11' F11D -59(2) . . . . ?
C9 C10 C11' F11D 62.5(19) . . . . ?
F10A C10 C11' F11C 67(2) . . . . ?
F10B C10 C11' F11C -177.5(17) . . . . ?
C9 C10 C11' F11C -56(2) . . . . ?
F10A C10 C11' C12' -55(3) . . . . ?
F10B C10 C11' C12' 61(3) . . . . ?
C9 C10 C11' C12' -177.7(19) . . . . ?
F11D C11' C12' F12E -173(3) . . . . ?
F11C C11' C12' F12E -57(3) . . . . ?
C10 C11' C12' F12E 68(3) . . . . ?
F11D C11' C12' F12F 66(3) . . . . ?
F11C C11' C12' F12F -178(3) . . . . ?
C10 C11' C12' F12F -53(3) . . . . ?
F11D C11' C12' F12D -53(3) . . . . ?
F11C C11' C12' F12D 64(3) . . . . ?
C10 C11' C12' F12D -172(3) . . . . ?
F13A C13 C14 F14B -175.4(5) . . . . ?
F13B C13 C14 F14B 67.5(6) . . . . ?
I1 C13 C14 F14B -52.2(5) . . . . ?
F13A C13 C14 F14A -58.8(6) . . . . ?
F13B C13 C14 F14A -175.8(5) . . . . ?
I1 C13 C14 F14A 64.4(5) . . . . ?
F13A C13 C14 C15 61.5(7) . . . . ?
F13B C13 C14 C15 -55.5(7) . . . . ?
I1 C13 C14 C15 -175.3(4) . . . . ?
F14B C14 C15 F15B -178.9(5) . . . . ?
F14A C14 C15 F15B 63.3(6) . . . . ?
C13 C14 C15 F15B -56.5(6) . . . . ?
F14B C14 C15 F15A -61.9(6) . . . . ?
F14A C14 C15 F15A -179.7(5) . . . . ?
C13 C14 C15 F15A 60.6(6) . . . . ?
F14B C14 C15 C16 58.7(6) . . . . ?
F14A C14 C15 C16 -59.1(6) . . . . ?
C13 C14 C15 C16 -178.8(5) . . . . ?
F15B C15 C16 F16B -170.9(4) . . . . ?
F15A C15 C16 F16B 72.4(6) . . . . ?
C14 C15 C16 F16B -48.4(6) . . . . ?
F15B C15 C16 F16A -55.5(6) . . . . ?
F15A C15 C16 F16A -172.3(5) . . . . ?
C14 C15 C16 F16A 67.0(6) . . . . ?
F15B C15 C16 C17' 60.6(9) . . . . ?
F15A C15 C16 C17' -56.1(9) . . . . ?
C14 C15 C16 C17' -176.9(8) . . . . ?
F15B C15 C16 C17 68.3(7) . . . . ?
F15A C15 C16 C17 -48.4(8) . . . . ?
C14 C15 C16 C17 -169.2(6) . . . . ?
F16B C16 C17 F17B -166.9(8) . . . . ?
F16A C16 C17 F17B 78.5(9) . . . . ?
C15 C16 C17 F17B -44.5(9) . . . . ?
F16B C16 C17 F17A -50.7(9) . . . . ?
F16A C16 C17 F17A -165.3(7) . . . . ?
C15 C16 C17 F17A 71.7(9) . . . . ?
F16B C16 C17 C18 69.4(8) . . . . ?
F16A C16 C17 C18 -45.3(9) . . . . ?
C15 C16 C17 C18 -168.2(6) . . . . ?
F17B C17 C18 F18A -166.3(8) . . . . ?
F17A C17 C18 F18A 77.2(9) . . . . ?
C16 C17 C18 F18A -42.9(9) . . . . ?
F17B C17 C18 F18B -51.3(10) . . . . ?
F17A C17 C18 F18B -167.8(9) . . . . ?
C16 C17 C18 F18B 72.1(9) . . . . ?
F17B C17 C18 C19 70.5(9) . . . . ?
F17A C17 C18 C19 -46.0(10) . . . . ?
C16 C17 C18 C19 -166.1(8) . . . . ?
F18A C18 C19 F19A -170.1(9) . . . . ?
F18B C18 C19 F19A 74.8(10) . . . . ?
C17 C18 C19 F19A -47.1(10) . . . . ?
F18A C18 C19 F19B -49.9(10) . . . . ?
F18B C18 C19 F19B -165.0(9) . . . . ?
C17 C18 C19 F19B 73.2(10) . . . . ?
F18A C18 C19 C20 69.9(9) . . . . ?
F18B C18 C19 C20 -45.2(10) . . . . ?
C17 C18 C19 C20 -167.0(7) . . . . ?
F19A C19 C20 F20B -174.1(10) . . . . ?
F19B C19 C20 F20B 68.1(10) . . . . ?
C18 C19 C20 F20B -52.9(10) . . . . ?
F19A C19 C20 F20A 68.8(10) . . . . ?
F19B C19 C20 F20A -49.1(10) . . . . ?
C18 C19 C20 F20A -170.0(8) . . . . ?
F19A C19 C20 F20C -51.9(11) . . . . ?
F19B C19 C20 F20C -169.7(10) . . . . ?
C18 C19 C20 F20C 69.3(11) . . . . ?
F16B C16 C17' F17D 178.0(11) . . . . ?
F16A C16 C17' F17D 62.6(12) . . . . ?
C15 C16 C17' F17D -55.4(12) . . . . ?
F16B C16 C17' F17C -66.1(12) . . . . ?
F16A C16 C17' F17C 178.5(11) . . . . ?
C15 C16 C17' F17C 60.5(11) . . . . ?
F16B C16 C17' C18' 55.2(11) . . . . ?
F16A C16 C17' C18' -60.2(11) . . . . ?
C15 C16 C17' C18' -178.2(8) . . . . ?
F17D C17' C18' F18C -179.8(12) . . . . ?
F17C C17' C18' F18C 64.9(13) . . . . ?
C16 C17' C18' F18C -56.8(12) . . . . ?
F17D C17' C18' F18D -63.9(14) . . . . ?
F17C C17' C18' F18D -179.2(13) . . . . ?
C16 C17' C18' F18D 59.1(13) . . . . ?
F17D C17' C18' C19' 57.4(13) . . . . ?
F17C C17' C18' C19' -57.9(13) . . . . ?
C16 C17' C18' C19' -179.6(11) . . . . ?
F18C C18' C19' F19C 176.0(13) . . . . ?
F18D C18' C19' F19C 60.8(14) . . . . ?
C17' C18' C19' F19C -60.7(13) . . . . ?
F18C C18' C19' F19D -65.4(16) . . . . ?
F18D C18' C19' F19D 179.4(14) . . . . ?
C17' C18' C19' F19D 57.9(14) . . . . ?
F18C C18' C19' C20' 55.2(12) . . . . ?
F18D C18' C19' C20' -60.0(13) . . . . ?
C17' C18' C19' C20' 178.5(10) . . . . ?
F19C C19' C20' F20D 53.1(14) . . . . ?
F19D C19' C20' F20D -64.9(15) . . . . ?
C18' C19' C20' F20D 174.0(11) . . . . ?
F19C C19' C20' F20F -66.9(15) . . . . ?
F19D C19' C20' F20F 175.0(16) . . . . ?
C18' C19' C20' F20F 53.9(15) . . . . ?
F19C C19' C20' F20E 172.6(14) . . . . ?
F19D C19' C20' F20E 54.5(16) . . . . ?
C18' C19' C20' F20E -66.6(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 I2 0.90(2) 2.59(3) 3.462(5) 165(5) 1_565

_refine_diff_density_max         0.691
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.123

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_s406
_database_code_depnum_ccdc_archive 'CCDC 1416727'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 F26 I N2 S'
_chemical_formula_weight         934.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8881(3)
_cell_length_b                   10.2741(7)
_cell_length_c                   25.4810(10)
_cell_angle_alpha                89.763(4)
_cell_angle_beta                 87.419(4)
_cell_angle_gamma                77.726(3)
_cell_volume                     1504.69(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    23346
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      25.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.062
_exptl_crystal_F_000             900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.313
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      233(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7370
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.177
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.918
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.918
_reflns_number_total             4840
_reflns_number_gt                3459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       COLLECT
_computing_cell_refinement       ?
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0994P)²+0.0698P] 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         4840
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1684
_refine_ls_wR_factor_gt          0.1519
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.31334(8) 0.21798(5) 0.05219(2) 0.0587(2) Uani 1 1 d . . . . .
S1 S 0.2121(3) 0.39520(17) -0.10328(7) 0.0504(4) Uani 1 1 d . . . . .
N2 N 0.1733(9) 0.1316(5) -0.0979(2) 0.0457(13) Uani 1 1 d . . . . .
N1 N -0.0983(9) 0.2657(5) -0.05250(19) 0.0457(13) Uani 1 1 d . . . . .
C1 C 0.0884(10) 0.2607(7) -0.0848(2) 0.0435(15) Uani 1 1 d . . . . .
C2 C 0.0370(13) 0.0579(7) -0.0740(3) 0.0527(17) Uani 1 1 d . . . . .
H2 H 0.0562 -0.0351 -0.0767 0.063 Uiso 1 1 calc R U . . .
C3 C -0.1288(12) 0.1386(7) -0.0461(3) 0.0537(18) Uani 1 1 d . . . . .
H3 H -0.2477 0.1128 -0.0254 0.064 Uiso 1 1 calc R U . . .
C4 C -0.2295(11) 0.3860(7) -0.0252(3) 0.0567(18) Uani 1 1 d . . . . .
H4A H -0.1743 0.3890 0.0100 0.085 Uiso 1 1 calc R U . . .
H4B H -0.3936 0.3841 -0.0231 0.085 Uiso 1 1 calc R U . . .
H4C H -0.2070 0.4644 -0.0444 0.085 Uiso 1 1 calc R U . . .
C5 C 0.0671(15) 0.4445(10) -0.1647(4) 0.091(3) Uani 1 1 d . . . . .
H5A H 0.1280 0.5191 -0.1795 0.110 Uiso 1 1 calc R U . . .
H5B H 0.1119 0.3700 -0.1896 0.110 Uiso 1 1 calc R U . . .
C6 C -0.1816(14) 0.4829(10) -0.1618(4) 0.081(3) Uani 1 1 d . . . . .
H6A H -0.2283 0.5502 -0.1340 0.098 Uiso 1 1 calc R U . . .
H6B H -0.2442 0.4051 -0.1515 0.098 Uiso 1 1 calc R U . . .
C7 C -0.2916(15) 0.5380(9) -0.2116(3) 0.068(2) Uani 1 1 d . . . . .
C8 C -0.3135(11) 0.4406(8) -0.2568(3) 0.0566(18) Uani 1 1 d . . . . .
C9 C -0.4596(11) 0.4987(7) -0.3036(3) 0.0515(17) Uani 1 1 d . . . . .
C10 C -0.4762(12) 0.3989(7) -0.3482(3) 0.0545(18) Uani 1 1 d . . . . .
C11 C -0.6251(15) 0.4551(9) -0.3931(3) 0.070(2) Uani 1 1 d . . . . .
C12 C -0.641(2) 0.3592(11) -0.4380(4) 0.089(3) Uani 1 1 d . . . . .
C13 C 0.3854(11) 0.0790(7) -0.1306(3) 0.0542(17) Uani 1 1 d . . . . .
H13A H 0.5098 0.0369 -0.1079 0.065 Uiso 1 1 calc R U . . .
H13B H 0.4356 0.1531 -0.1487 0.065 Uiso 1 1 calc R U . . .
C14 C 0.3488(11) -0.0231(7) -0.1715(3) 0.0549(18) Uani 1 1 d . . . . .
H14A H 0.5007 -0.0692 -0.1865 0.066 Uiso 1 1 calc R U . . .
H14B H 0.2757 -0.0898 -0.1540 0.066 Uiso 1 1 calc R U . . .
C15 C 0.1998(11) 0.0388(7) -0.2152(3) 0.0498(17) Uani 1 1 d . . . . .
C16 C 0.1727(12) -0.0616(7) -0.2581(3) 0.0527(17) Uani 1 1 d . . . . .
C17 C 0.0318(11) -0.0047(7) -0.3059(3) 0.0503(17) Uani 1 1 d . . . . .
C18 C 0.0124(12) -0.1058(8) -0.3492(3) 0.0548(18) Uani 1 1 d . . . . .
C19 C -0.1324(16) -0.0500(9) -0.3951(3) 0.072(2) Uani 1 1 d . . . . .
C20 C -0.1534(17) -0.1464(11) -0.4397(3) 0.078(2) Uani 1 1 d . . . . .
F1 F -0.5108(9) 0.6052(6) -0.19660(19) 0.0932(16) Uani 1 1 d . . . . .
F2 F -0.1782(8) 0.6297(5) -0.23345(17) 0.0767(13) Uani 1 1 d . . . . .
F3 F -0.4140(8) 0.3458(5) -0.23418(18) 0.0759(12) Uani 1 1 d . . . . .
F4 F -0.1009(7) 0.3803(5) -0.2742(2) 0.0854(14) Uani 1 1 d . . . . .
F5 F -0.6735(7) 0.5492(5) -0.28532(16) 0.0798(14) Uani 1 1 d . . . . .
F6 F -0.3674(9) 0.5949(5) -0.32439(18) 0.0831(14) Uani 1 1 d . . . . .
F7 F -0.5637(11) 0.2995(6) -0.3273(2) 0.0996(17) Uani 1 1 d . . . . .
F8 F -0.2625(9) 0.3456(6) -0.3673(2) 0.107(2) Uani 1 1 d . . . . .
F9 F -0.8444(9) 0.5025(7) -0.3746(2) 0.122(2) Uani 1 1 d . . . . .
F10 F -0.5509(14) 0.5559(7) -0.4138(2) 0.127(3) Uani 1 1 d . . . . .
F11 F -0.7322(17) 0.2600(8) -0.4206(3) 0.160(3) Uani 1 1 d . . . . .
F12 F -0.4438(14) 0.3103(10) -0.4600(3) 0.176(4) Uani 1 1 d . . . . .
F13 F -0.7731(13) 0.4169(7) -0.4741(2) 0.130(2) Uani 1 1 d . . . . .
F14 F 0.2896(9) 0.1376(5) -0.23842(17) 0.0831(14) Uani 1 1 d . . . . .
F15 F -0.0159(7) 0.0981(5) -0.19644(16) 0.0744(13) Uani 1 1 d . . . . .
F16 F 0.3888(7) -0.1223(5) -0.27591(17) 0.0793(14) Uani 1 1 d . . . . .
F17 F 0.0746(9) -0.1544(5) -0.23538(17) 0.0832(14) Uani 1 1 d . . . . .
F18 F 0.1319(11) 0.0880(5) -0.32822(19) 0.0962(17) Uani 1 1 d . . . . .
F19 F -0.1810(8) 0.0527(6) -0.28800(19) 0.0960(18) Uani 1 1 d . . . . .
F20 F 0.2230(9) -0.1632(6) -0.3670(2) 0.110(2) Uani 1 1 d . . . . .
F21 F -0.0839(12) -0.2008(6) -0.3274(2) 0.110(2) Uani 1 1 d . . . . .
F22 F -0.0622(17) 0.0490(7) -0.4156(2) 0.153(3) Uani 1 1 d . . . . .
F23 F -0.3532(11) 0.0017(8) -0.3774(2) 0.142(3) Uani 1 1 d . . . . .
F24 F 0.0428(15) -0.1969(11) -0.4607(3) 0.191(5) Uani 1 1 d . . . . .
F25 F -0.2328(19) -0.2440(9) -0.4223(3) 0.182(4) Uani 1 1 d . . . . .
F26 F -0.2787(13) -0.0908(7) -0.4760(2) 0.132(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.747(7) . ?
S1 C5 1.835(9) . ?
N2 C2 1.341(9) . ?
N2 C1 1.352(8) . ?
N2 C13 1.473(8) . ?
N1 C1 1.336(8) . ?
N1 C3 1.363(9) . ?
N1 C4 1.471(9) . ?
C2 C3 1.320(10) . ?
C2 H2 0.9400 . ?
C3 H3 0.9400 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C5 C6 1.432(11) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.504(11) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 F1 1.367(10) . ?
C7 F2 1.369(9) . ?
C7 C8 1.556(11) . ?
C8 F4 1.330(8) . ?
C8 F3 1.356(8) . ?
C8 C9 1.545(10) . ?
C9 F5 1.320(8) . ?
C9 F6 1.323(8) . ?
C9 C10 1.554(10) . ?
C10 F8 1.332(8) . ?
C10 F7 1.336(9) . ?
C10 C11 1.512(11) . ?
C11 F10 1.307(10) . ?
C11 F9 1.344(10) . ?
C11 C12 1.532(11) . ?
C12 F12 1.270(12) . ?
C12 F13 1.291(12) . ?
C12 F11 1.315(12) . ?
C13 C14 1.536(9) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.503(10) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 F15 1.353(7) . ?
C15 F14 1.361(8) . ?
C15 C16 1.542(9) . ?
C16 F17 1.333(8) . ?
C16 F16 1.352(8) . ?
C16 C17 1.548(10) . ?
C17 F19 1.328(8) . ?
C17 F18 1.334(9) . ?
C17 C18 1.542(9) . ?
C18 F20 1.317(8) . ?
C18 F21 1.336(9) . ?
C18 C19 1.517(11) . ?
C19 F22 1.278(10) . ?
C19 F23 1.353(10) . ?
C19 C20 1.536(11) . ?
C20 F24 1.259(11) . ?
C20 F25 1.264(11) . ?
C20 F26 1.268(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
C1 S1 C5 100.8(3) . . ?
C2 N2 C1 108.3(6) . . ?
C2 N2 C13 125.4(6) . . ?
C1 N2 C13 126.3(6) . . ?
C1 N1 C3 107.5(5) . . ?
C1 N1 C4 125.1(5) . . ?
C3 N1 C4 127.1(6) . . ?
N1 C1 N2 107.6(5) . . ?
N1 C1 S1 126.2(5) . . ?
N2 C1 S1 126.1(5) . . ?
C3 C2 N2 108.1(6) . . ?
C3 C2 H2 125.9 . . ?
N2 C2 H2 125.9 . . ?
C2 C3 N1 108.4(6) . . ?
C2 C3 H3 125.8 . . ?
N1 C3 H3 125.8 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S1 117.3(7) . . ?
C6 C5 H5A 108.0 . . ?
S1 C5 H5A 108.0 . . ?
C6 C5 H5B 108.0 . . ?
S1 C5 H5B 108.0 . . ?
H5A C5 H5B 107.2 . . ?
C5 C6 C7 115.5(8) . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C7 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
F1 C7 F2 106.8(7) . . ?
F1 C7 C6 105.6(7) . . ?
F2 C7 C6 110.7(6) . . ?
F1 C7 C8 107.8(5) . . ?
F2 C7 C8 106.1(6) . . ?
C6 C7 C8 119.3(7) . . ?
F4 C8 F3 107.1(6) . . ?
F4 C8 C9 109.8(6) . . ?
F3 C8 C9 107.8(5) . . ?
F4 C8 C7 108.7(6) . . ?
F3 C8 C7 105.6(6) . . ?
C9 C8 C7 117.4(6) . . ?
F5 C9 F6 109.4(6) . . ?
F5 C9 C8 108.1(5) . . ?
F6 C9 C8 107.9(5) . . ?
F5 C9 C10 107.5(5) . . ?
F6 C9 C10 107.9(6) . . ?
C8 C9 C10 116.0(6) . . ?
F8 C10 F7 107.0(7) . . ?
F8 C10 C11 108.8(6) . . ?
F7 C10 C11 107.5(6) . . ?
F8 C10 C9 109.0(6) . . ?
F7 C10 C9 108.4(6) . . ?
C11 C10 C9 115.9(6) . . ?
F10 C11 F9 106.8(8) . . ?
F10 C11 C10 109.9(7) . . ?
F9 C11 C10 109.3(6) . . ?
F10 C11 C12 107.3(8) . . ?
F9 C11 C12 106.2(7) . . ?
C10 C11 C12 116.9(8) . . ?
F12 C12 F13 107.2(9) . . ?
F12 C12 F11 108.0(10) . . ?
F13 C12 F11 106.6(9) . . ?
F12 C12 C11 112.3(9) . . ?
F13 C12 C11 111.9(9) . . ?
F11 C12 C11 110.6(9) . . ?
N2 C13 C14 112.6(5) . . ?
N2 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 113.0(6) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
F15 C15 F14 105.6(6) . . ?
F15 C15 C14 110.9(5) . . ?
F14 C15 C14 110.4(6) . . ?
F15 C15 C16 107.7(5) . . ?
F14 C15 C16 108.3(5) . . ?
C14 C15 C16 113.5(6) . . ?
F17 C16 F16 107.4(6) . . ?
F17 C16 C15 107.8(6) . . ?
F16 C16 C15 107.4(5) . . ?
F17 C16 C17 109.0(5) . . ?
F16 C16 C17 108.1(5) . . ?
C15 C16 C17 116.8(6) . . ?
F19 C17 F18 108.8(6) . . ?
F19 C17 C18 108.6(5) . . ?
F18 C17 C18 107.3(6) . . ?
F19 C17 C16 107.5(5) . . ?
F18 C17 C16 108.3(5) . . ?
C18 C17 C16 116.1(6) . . ?
F20 C18 F21 107.3(7) . . ?
F20 C18 C19 109.0(6) . . ?
F21 C18 C19 107.3(6) . . ?
F20 C18 C17 108.9(6) . . ?
F21 C18 C17 108.2(6) . . ?
C19 C18 C17 115.7(7) . . ?
F22 C19 F23 104.3(9) . . ?
F22 C19 C18 111.1(7) . . ?
F23 C19 C18 109.3(7) . . ?
F22 C19 C20 107.8(8) . . ?
F23 C19 C20 105.6(7) . . ?
C18 C19 C20 117.7(8) . . ?
F24 C20 F25 105.2(11) . . ?
F24 C20 F26 106.7(9) . . ?
F25 C20 F26 109.2(9) . . ?
F24 C20 C19 111.2(8) . . ?
F25 C20 C19 111.1(8) . . ?
F26 C20 C19 113.1(9) . . ?

_refine_diff_density_max         1.372
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.105



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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1416728'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 F13 N2 O3 S2'
_chemical_formula_sum            'C15 H15 F13 N2 O3 S2'
_chemical_formula_weight         582.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   8.6657(2)
_cell_length_b                   10.1187(4)
_cell_length_c                   48.601(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4261.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    21274
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      25.3

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_F_000             2336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.385
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      233(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16437
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         2.495
_diffrn_reflns_theta_max         25.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3820
_reflns_number_gt                2650
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

 The C6F13 fragment is 50/50 disordered over two positions.
 1139 restraints on distances and thermal parameters have been
 used in the disorder refinement  

;

_computing_data_collection       COLLECT
_computing_cell_refinement       ?
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+6.9973P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3820
_refine_ls_number_parameters     455
_refine_ls_number_restraints     1139
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.13967(12) 0.96016(10) 0.14344(2) 0.0448(3) Uani 1 1 d . . . . .
S2 S 0.07284(11) 0.57966(8) 0.19460(2) 0.0345(3) Uani 1 1 d . . . . .
O1 O -0.0688(3) 0.5853(3) 0.17865(6) 0.0505(7) Uani 1 1 d . . . . .
O2 O 0.2078(3) 0.5551(3) 0.17787(6) 0.0499(7) Uani 1 1 d . . . . .
O3 O 0.0606(4) 0.4906(2) 0.21803(5) 0.0587(8) Uani 1 1 d . . . . .
N1 N -0.0352(3) 1.1645(3) 0.17571(6) 0.0335(7) Uani 1 1 d . . . . .
N2 N -0.0985(3) 0.9918(2) 0.19913(6) 0.0301(6) Uani 1 1 d . . . . .
C1 C -0.0867(4) 1.0401(3) 0.17358(7) 0.0314(8) Uani 1 1 d . . . . .
C2 C -0.0120(4) 1.1939(3) 0.20274(7) 0.0351(8) Uani 1 1 d . . . . .
H2 H 0.0260 1.2740 0.2098 0.042 Uiso 1 1 calc R U . . .
C3 C -0.0535(4) 1.0869(3) 0.21746(7) 0.0336(8) Uani 1 1 d . . . . .
H3 H -0.0519 1.0790 0.2367 0.040 Uiso 1 1 calc R U . . .
C4 C -0.0010(5) 1.2528(4) 0.15264(8) 0.0491(10) Uani 1 1 d . . . . .
H4A H 0.1035 1.2373 0.1463 0.074 Uiso 1 1 calc R U . . .
H4B H -0.0112 1.3439 0.1586 0.074 Uiso 1 1 calc R U . . .
H4C H -0.0728 1.2358 0.1377 0.074 Uiso 1 1 calc R U . . .
C5 C -0.1597(4) 0.8623(3) 0.20720(8) 0.0361(8) Uani 1 1 d . . . . .
H5A H -0.1832 0.8108 0.1907 0.043 Uiso 1 1 calc R U . . .
H5B H -0.2560 0.8746 0.2175 0.043 Uiso 1 1 calc R U . . .
C6 C -0.0459(4) 0.7867(3) 0.22482(7) 0.0383(9) Uani 1 1 d . . . . .
H6A H -0.0984 0.7098 0.2327 0.046 Uiso 1 1 calc R U . . .
H6B H -0.0131 0.8434 0.2401 0.046 Uiso 1 1 calc R U . . .
C7 C 0.0973(4) 0.7393(3) 0.20937(7) 0.0373(8) Uani 1 1 d . . . . .
H7A H 0.1850 0.7371 0.2221 0.045 Uiso 1 1 calc R U . . .
H7B H 0.1217 0.8026 0.1947 0.045 Uiso 1 1 calc R U . . .
C8 C 0.0509(5) 0.9266(4) 0.12886(9) 0.0554(11) Uani 1 1 d D . . . .
H8A H 0.0611 0.9759 0.1116 0.069(14) Uiso 1 1 calc R . . . .
H8B H 0.1294 0.9600 0.1416 0.093(17) Uiso 1 1 calc R . . . .
C9 C 0.0838(5) 0.7828(4) 0.12317(8) 0.0565(11) Uani 1 1 d D . . . .
H9A H 0.0555 0.7313 0.1395 0.068 Uiso 1 1 calc R U . A 1
H9B H 0.1951 0.7722 0.1203 0.068 Uiso 1 1 calc R U . A 1
C10 C 0.0000(12) 0.7254(9) 0.09847(19) 0.0463(10) Uani 0.5 1 d D . P B 1
C11 C 0.0437(13) 0.5838(9) 0.0912(2) 0.0505(11) Uani 0.5 1 d D . P B 1
C12 C -0.0343(12) 0.5161(9) 0.0669(2) 0.0530(11) Uani 0.5 1 d D . P B 1
C13 C 0.0203(12) 0.3765(9) 0.05978(19) 0.0580(14) Uani 0.5 1 d D . P B 1
C14 C -0.0546(11) 0.3080(8) 0.03536(19) 0.0777(17) Uani 0.5 1 d D . P B 1
C15 C -0.0018(11) 0.1689(8) 0.0281(2) 0.089(2) Uani 0.5 1 d D . P B 1
F1 F 0.032(2) 0.8014(16) 0.0764(2) 0.080(6) Uani 0.5 1 d D U P B 1
F2 F -0.1535(10) 0.7322(16) 0.1021(3) 0.066(5) Uani 0.5 1 d D U P B 1
F3 F 0.1965(11) 0.5844(11) 0.0861(2) 0.066(4) Uani 0.5 1 d D U P B 1
F4 F 0.019(2) 0.5077(14) 0.1134(2) 0.086(5) Uani 0.5 1 d D U P B 1
F5 F -0.015(2) 0.5916(12) 0.0446(2) 0.084(5) Uani 0.5 1 d D U P B 1
F6 F -0.1850(11) 0.5111(16) 0.0722(4) 0.093(5) Uani 0.5 1 d D U P B 1
F7 F 0.1707(11) 0.3785(13) 0.0550(3) 0.107(5) Uani 0.5 1 d D U P B 1
F8 F -0.0030(16) 0.2994(13) 0.0816(2) 0.101(5) Uani 0.5 1 d D U P B 1
F9 F -0.0280(18) 0.3812(11) 0.0130(2) 0.162(6) Uani 0.5 1 d D U P B 1
F10 F -0.2052(8) 0.3044(10) 0.0402(2) 0.096(4) Uani 0.5 1 d D U P B 1
F11 F 0.1465(9) 0.1647(9) 0.0241(3) 0.102(3) Uani 0.5 1 d D U P B 1
F12 F -0.0333(12) 0.0877(9) 0.0482(2) 0.116(4) Uani 0.5 1 d D U P B 1
F13 F -0.0697(18) 0.1335(15) 0.0051(3) 0.145(6) Uani 0.5 1 d D U P B 1
C10' C -0.0034(12) 0.7246(9) 0.09902(19) 0.0463(10) Uani 0.5 1 d D . P B 2
C11' C 0.0503(12) 0.5864(9) 0.0910(2) 0.0505(11) Uani 0.5 1 d D . P B 2
C12' C -0.0390(12) 0.5144(9) 0.0686(2) 0.0530(11) Uani 0.5 1 d D . P B 2
C13' C 0.0304(12) 0.3873(9) 0.0569(2) 0.0580(14) Uani 0.5 1 d D . P B 2
C14' C -0.0701(12) 0.3084(10) 0.0374(2) 0.0777(17) Uani 0.5 1 d D . P B 2
C15' C -0.0051(14) 0.1868(10) 0.0234(3) 0.089(2) Uani 0.5 1 d D . P B 2
F1' F 0.012(2) 0.8039(13) 0.0769(2) 0.061(4) Uani 0.5 1 d D U P B 2
F2' F -0.1552(10) 0.7205(17) 0.1047(3) 0.076(5) Uani 0.5 1 d D U P B 2
F3' F 0.1989(11) 0.5959(15) 0.0833(3) 0.102(6) Uani 0.5 1 d D U P B 2
F4' F 0.046(2) 0.5108(13) 0.1137(2) 0.087(5) Uani 0.5 1 d D U P B 2
F5' F -0.059(2) 0.5977(14) 0.0476(3) 0.089(5) Uani 0.5 1 d D U P B 2
F6' F -0.1782(12) 0.4863(16) 0.0790(4) 0.101(6) Uani 0.5 1 d D U P B 2
F7' F 0.1577(13) 0.4196(14) 0.0429(3) 0.109(5) Uani 0.5 1 d D U P B 2
F8' F 0.0746(17) 0.3101(13) 0.0775(2) 0.116(6) Uani 0.5 1 d D U P B 2
F9' F -0.1148(14) 0.3883(12) 0.0172(2) 0.117(5) Uani 0.5 1 d D U P B 2
F10' F -0.1892(17) 0.2685(16) 0.0517(3) 0.222(9) Uani 0.5 1 d D U P B 2
F11' F 0.0898(16) 0.2283(12) 0.0043(2) 0.172(5) Uani 0.5 1 d D U P B 2
F12' F 0.074(2) 0.1106(11) 0.0400(3) 0.168(6) Uani 0.5 1 d D U P B 2
F13' F -0.1129(16) 0.1134(19) 0.0118(3) 0.136(6) Uani 0.5 1 d D U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.736(3) . ?
S1 C8 1.829(4) . ?
S2 O2 1.446(3) . ?
S2 O1 1.453(3) . ?
S2 O3 1.456(3) . ?
S2 C7 1.780(3) . ?
N1 C1 1.339(4) . ?
N1 C2 1.362(4) . ?
N1 C4 1.464(4) . ?
N2 C1 1.339(4) . ?
N2 C3 1.368(4) . ?
N2 C5 1.467(4) . ?
C2 C3 1.347(5) . ?
C2 H2 0.9400 . ?
C3 H3 0.9400 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C5 C6 1.514(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.527(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.508(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10' 1.515(6) . ?
C9 C10 1.519(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 F2 1.344(8) . ?
C10 F1 1.350(8) . ?
C10 C11 1.523(6) . ?
C11 F4 1.342(8) . ?
C11 F3 1.348(8) . ?
C11 C12 1.525(6) . ?
C12 F6 1.332(8) . ?
C12 F5 1.335(8) . ?
C12 C13 1.530(6) . ?
C13 F7 1.324(8) . ?
C13 F8 1.330(8) . ?
C13 C14 1.520(6) . ?
C14 F10 1.327(8) . ?
C14 F9 1.336(8) . ?
C14 C15 1.521(6) . ?
C15 F13 1.315(8) . ?
C15 F11 1.301(8) . ?
C15 F12 1.304(9) . ?
C10' F2' 1.345(8) . ?
C10' F1' 1.347(8) . ?
C10' C11' 1.525(6) . ?
C11' F4' 1.343(8) . ?
C11' F3' 1.344(8) . ?
C11' C12' 1.522(6) . ?
C12' F5' 1.334(8) . ?
C12' F6' 1.339(8) . ?
C12' C13' 1.529(6) . ?
C13' F8' 1.327(8) . ?
C13' F7' 1.338(8) . ?
C13' C14' 1.514(6) . ?
C14' F9' 1.328(9) . ?
C14' F10' 1.309(9) . ?
C14' C15' 1.514(7) . ?
C15' F12' 1.309(9) . ?
C15' F13' 1.322(9) . ?
C15' F11' 1.312(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C8 100.07(18) . . ?
O2 S2 O1 112.94(17) . . ?
O2 S2 O3 113.11(18) . . ?
O1 S2 O3 112.35(18) . . ?
O2 S2 C7 106.64(16) . . ?
O1 S2 C7 106.27(16) . . ?
O3 S2 C7 104.76(16) . . ?
C1 N1 C2 109.2(3) . . ?
C1 N1 C4 125.6(3) . . ?
C2 N1 C4 125.1(3) . . ?
C1 N2 C3 109.0(3) . . ?
C1 N2 C5 127.0(3) . . ?
C3 N2 C5 123.9(3) . . ?
N2 C1 N1 107.3(3) . . ?
N2 C1 S1 126.3(3) . . ?
N1 C1 S1 126.2(3) . . ?
C3 C2 N1 107.3(3) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
C2 C3 N2 107.2(3) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 111.5(3) . . ?
N2 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 114.2(3) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 S2 112.7(2) . . ?
C6 C7 H7A 109.0 . . ?
S2 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
S2 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 S1 114.9(3) . . ?
C9 C8 H8A 108.5 . . ?
S1 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
S1 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C10' 115.0(5) . . ?
C8 C9 C10 115.1(5) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
F2 C10 F1 106.2(8) . . ?
F2 C10 C9 110.5(7) . . ?
F1 C10 C9 108.2(8) . . ?
F2 C10 C11 108.9(7) . . ?
F1 C10 C11 107.5(8) . . ?
C9 C10 C11 115.1(6) . . ?
F4 C11 F3 107.9(8) . . ?
F4 C11 C10 108.3(7) . . ?
F3 C11 C10 106.4(6) . . ?
F4 C11 C12 107.2(7) . . ?
F3 C11 C12 107.2(6) . . ?
C10 C11 C12 119.5(6) . . ?
F6 C12 F5 107.6(8) . . ?
F6 C12 C11 107.5(7) . . ?
F5 C12 C11 108.4(7) . . ?
F6 C12 C13 108.2(7) . . ?
F5 C12 C13 107.9(7) . . ?
C11 C12 C13 116.9(6) . . ?
F7 C13 F8 107.3(8) . . ?
F7 C13 C14 106.9(7) . . ?
F8 C13 C14 106.8(7) . . ?
F7 C13 C12 109.2(7) . . ?
F8 C13 C12 108.4(7) . . ?
C14 C13 C12 117.7(6) . . ?
F10 C14 F9 109.2(9) . . ?
F10 C14 C15 108.2(7) . . ?
F9 C14 C15 105.9(7) . . ?
F10 C14 C13 107.1(7) . . ?
F9 C14 C13 108.0(7) . . ?
C15 C14 C13 118.3(7) . . ?
F13 C15 F11 107.7(9) . . ?
F13 C15 C14 108.3(8) . . ?
F11 C15 C14 111.3(8) . . ?
F13 C15 F12 111.7(9) . . ?
F11 C15 F12 107.4(8) . . ?
C14 C15 F12 110.4(7) . . ?
F2' C10' F1' 106.2(8) . . ?
F2' C10' C9 109.9(7) . . ?
F1' C10' C9 109.7(7) . . ?
F2' C10' C11' 108.8(7) . . ?
F1' C10' C11' 108.2(7) . . ?
C9 C10' C11' 113.8(6) . . ?
F4' C11' F3' 107.1(9) . . ?
F4' C11' C12' 107.6(7) . . ?
F3' C11' C12' 108.8(7) . . ?
F4' C11' C10' 107.6(7) . . ?
F3' C11' C10' 107.3(7) . . ?
C12' C11' C10' 117.9(6) . . ?
F5' C12' F6' 107.8(9) . . ?
F5' C12' C11' 108.2(7) . . ?
F6' C12' C11' 106.8(7) . . ?
F5' C12' C13' 107.4(7) . . ?
F6' C12' C13' 108.4(7) . . ?
C11' C12' C13' 117.9(6) . . ?
F8' C13' F7' 106.9(8) . . ?
F8' C13' C14' 109.2(7) . . ?
F7' C13' C14' 106.5(8) . . ?
F8' C13' C12' 109.2(7) . . ?
F7' C13' C12' 107.9(7) . . ?
C14' C13' C12' 116.7(7) . . ?
F9' C14' F10' 110.5(10) . . ?
F9' C14' C13' 108.0(8) . . ?
F10' C14' C13' 106.5(10) . . ?
F9' C14' C15' 105.8(10) . . ?
F10' C14' C15' 106.3(10) . . ?
C13' C14' C15' 119.6(8) . . ?
F12' C15' F13' 107.6(10) . . ?
F12' C15' C14' 113.4(10) . . ?
F13' C15' C14' 112.7(12) . . ?
F12' C15' F11' 107.3(10) . . ?
F13' C15' F11' 108.6(9) . . ?
C14' C15' F11' 106.9(9) . . ?

_refine_diff_density_max         0.449
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.065

_shelxl_version_number           2014/6



