# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1545539'
_audit_update_record             
;
2017-04-24 deposited with the CCDC.
2017-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
2,5-bis(chloromethyl)-1,4-bis[9trifluoromethyl0sulfonyl]piperazine
_chemical_name_common            ?
_chemical_melting_point          461
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H5 Cl F3 N O2 S'
_chemical_formula_weight         223.60

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'
Cl Cl 0.1484 0.1585 '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                   8.8090(4)
_cell_length_b                   12.7998(6)
_cell_length_c                   7.2200(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.795(2)
_cell_angle_gamma                90
_cell_volume                     813.68(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    175
_cell_measurement_theta_min      5
_cell_measurement_theta_max      25

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.737
_shelx_estimated_absorpt_T_min   0.733
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6398
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21282
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.808
_diffrn_reflns_theta_max         30.050
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2381
_reflns_number_gt                2124
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0307P)²+0.4853P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2381
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0671
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
Cl1 Cl 0.20177(4) 0.78462(3) 0.52014(4) 0.02246(9) Uani 1 1 d . . . . .
S1 S 0.33868(3) 1.07763(2) 0.15781(4) 0.01398(8) Uani 1 1 d . . . . .
F1 F 0.16475(11) 1.16422(9) 0.39785(16) 0.0453(3) Uani 1 1 d . . . . .
F2 F 0.05905(10) 1.14160(9) 0.12627(15) 0.0412(3) Uani 1 1 d . . . . .
F3 F 0.09144(10) 1.01132(8) 0.31050(14) 0.0350(2) Uani 1 1 d . . . . .
O1 O 0.31628(11) 0.99711(8) 0.02391(13) 0.0215(2) Uani 1 1 d . . . . .
O2 O 0.38978(11) 1.17930(8) 0.10866(14) 0.0240(2) Uani 1 1 d . . . . .
N1 N 0.43794(11) 1.03506(8) 0.33234(13) 0.01236(18) Uani 1 1 d . . . . .
C1 C 0.15101(15) 1.10025(12) 0.2541(2) 0.0243(3) Uani 1 1 d . . . . .
C2 C 0.47315(13) 0.92252(9) 0.35290(16) 0.0128(2) Uani 1 1 d . . . . .
H4 H 0.5756 0.9082 0.3063 0.015 Uiso 1 1 calc R U . . .
H5 H 0.3986 0.8809 0.2787 0.015 Uiso 1 1 calc R U . . .
C3 C 0.46737(13) 0.89093(9) 0.55644(16) 0.0124(2) Uani 1 1 d . . . . .
H1 H 0.5135 0.8198 0.5699 0.015 Uiso 1 1 calc R U . . .
C4 C 0.30762(14) 0.88665(9) 0.63257(17) 0.0153(2) Uani 1 1 d . . . . .
H3 H 0.2558 0.9544 0.6110 0.018 Uiso 1 1 calc R U . . .
H2 H 0.3138 0.8737 0.7678 0.018 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.7851(12) . ?
S1 O1 1.4226(10) . ?
S1 O2 1.4255(10) . ?
S1 N1 1.6063(10) . ?
S1 C1 1.8362(14) . ?
F1 C1 1.3248(18) . ?
F2 C1 1.3194(16) . ?
F3 C1 1.3230(18) . ?
N1 C2 1.4800(14) . ?
N1 C3 1.4819(14) 3_676 ?
C2 C3 1.5266(16) . ?
C2 H4 0.9900 . ?
C2 H5 0.9900 . ?
C3 N1 1.4819(14) 3_676 ?
C3 C4 1.5277(16) . ?
C3 H1 1.0000 . ?
C4 H3 0.9900 . ?
C4 H2 0.9900 . ?

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
O1 S1 O2 122.03(6) . . ?
O1 S1 N1 110.36(6) . . ?
O2 S1 N1 109.67(6) . . ?
O1 S1 C1 105.31(6) . . ?
O2 S1 C1 104.20(7) . . ?
N1 S1 C1 103.36(6) . . ?
C2 N1 C3 117.08(9) . 3_676 ?
C2 N1 S1 121.07(8) . . ?
C3 N1 S1 119.44(8) 3_676 . ?
F2 C1 F3 108.65(12) . . ?
F2 C1 F1 109.82(13) . . ?
F3 C1 F1 108.53(12) . . ?
F2 C1 S1 109.81(10) . . ?
F3 C1 S1 110.57(10) . . ?
F1 C1 S1 109.44(10) . . ?
N1 C2 C3 109.95(9) . . ?
N1 C2 H4 109.7 . . ?
C3 C2 H4 109.7 . . ?
N1 C2 H5 109.7 . . ?
C3 C2 H5 109.7 . . ?
H4 C2 H5 108.2 . . ?
N1 C3 C2 108.49(9) 3_676 . ?
N1 C3 C4 109.70(9) 3_676 . ?
C2 C3 C4 114.50(10) . . ?
N1 C3 H1 108.0 3_676 . ?
C2 C3 H1 108.0 . . ?
C4 C3 H1 108.0 . . ?
C3 C4 Cl1 109.67(8) . . ?
C3 C4 H3 109.7 . . ?
Cl1 C4 H3 109.7 . . ?
C3 C4 H2 109.7 . . ?
Cl1 C4 H2 109.7 . . ?
H3 C4 H2 108.2 . . ?

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
O1 S1 N1 C2 -9.39(11) . . . . ?
O2 S1 N1 C2 -146.55(9) . . . . ?
C1 S1 N1 C2 102.80(10) . . . . ?
O1 S1 N1 C3 152.48(8) . . . 3_676 ?
O2 S1 N1 C3 15.32(10) . . . 3_676 ?
C1 S1 N1 C3 -95.33(9) . . . 3_676 ?
O1 S1 C1 F2 -67.78(12) . . . . ?
O2 S1 C1 F2 61.75(12) . . . . ?
N1 S1 C1 F2 176.39(10) . . . . ?
O1 S1 C1 F3 52.10(11) . . . . ?
O2 S1 C1 F3 -178.37(10) . . . . ?
N1 S1 C1 F3 -63.73(11) . . . . ?
O1 S1 C1 F1 171.60(10) . . . . ?
O2 S1 C1 F1 -58.87(12) . . . . ?
N1 S1 C1 F1 55.77(12) . . . . ?
C3 N1 C2 C3 55.64(13) 3_676 . . . ?
S1 N1 C2 C3 -142.08(8) . . . . ?
N1 C2 C3 N1 -50.80(13) . . . 3_676 ?
N1 C2 C3 C4 72.09(12) . . . . ?
N1 C3 C4 Cl1 -171.93(8) 3_676 . . . ?
C2 C3 C4 Cl1 65.83(11) . . . . ?

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
C4 H2 O1 0.99 2.43 3.1583(15) 129.8 1_556
C4 H2 Cl1 0.99 2.92 3.6971(12) 136.3 4_576
C3 H1 O2 1.00 2.39 3.2305(15) 141.7 2_645
C4 H2 O1 0.99 2.43 3.1583(15) 129.8 1_556
C4 H2 Cl1 0.99 2.92 3.6971(12) 136.3 4_576
C3 H1 O2 1.00 2.39 3.2305(15) 141.7 2_645
C4 H2 O1 0.99 2.43 3.1583(15) 129.8 1_556
C4 H2 Cl1 0.99 2.92 3.6971(12) 136.3 4_576
C3 H1 O2 1.00 2.39 3.2305(15) 141.7 2_645
C3 H1 O2 1.00 2.39 3.2305(15) 141.7 2_645
C4 H2 Cl1 0.99 2.92 3.6971(12) 136.3 4_576
C4 H2 O1 0.99 2.43 3.1583(15) 129.8 1_556
C3 H1 O2 1.00 2.39 3.2305(15) 141.7 2_645
C4 H2 Cl1 0.99 2.92 3.6971(12) 136.3 4_576
C4 H2 O1 0.99 2.43 3.1583(15) 129.8 1_556
C3 H1 O2 1.00 2.39 3.2305(15) 141.7 2_645
C4 H2 Cl1 0.99 2.92 3.6971(12) 136.3 4_576
C4 H2 O1 0.99 2.43 3.1583(15) 129.8 1_556

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitryle'
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1520697'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
3,7,9-tris[(trifluoromethyl)sulfonyl]-3,7,9-triazabicyclo[3.3.1]nonane
_chemical_name_common            ?
_chemical_melting_point          456
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 F18 N6 O12 S6'
_chemical_formula_weight         1047.77

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      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                   11.214(4)
_cell_length_b                   11.857(5)
_cell_length_c                   14.874(7)
_cell_angle_alpha                73.267(14)
_cell_angle_beta                 78.954(14)
_cell_angle_gamma                80.979(14)
_cell_volume                     1848.0(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    124
_cell_measurement_theta_min      5
_cell_measurement_theta_max      25

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_F_000             1050
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.37
_exptl_absorpt_coefficient_mu    0.525
_shelx_estimated_absorpt_T_min   0.780
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_T_max  0.830
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40457
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.174
_diffrn_reflns_theta_max         30.439
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             9983
_reflns_number_gt                7103
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1227P)²+9.1291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9983
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.2648
_refine_ls_wR_factor_gt          0.2262
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.66899(11) 0.57281(10) 0.23866(8) 0.0279(3) Uani 1 1 d . . . . .
S2 S 0.45217(10) 0.74090(9) 0.42824(7) 0.0213(2) Uani 1 1 d . . . . .
S3 S 0.97023(9) 0.73902(9) 0.44119(7) 0.0200(2) Uani 1 1 d . . . . .
S4 S 0.36167(10) 0.93073(9) -0.11899(7) 0.0221(2) Uani 1 1 d . . . . .
S5 S 0.17201(11) 1.10229(10) 0.07670(9) 0.0292(3) Uani 1 1 d . . . . .
S6 S 0.20695(11) 0.59309(9) 0.24331(7) 0.0238(2) Uani 1 1 d . . . . .
F1 F 0.8530(5) 0.4166(4) 0.2135(4) 0.0945(19) Uani 1 1 d . . . . .
F2 F 0.2564(4) 0.8286(5) 0.5198(5) 0.108(2) Uani 1 1 d . . . . .
F3 F 0.8626(5) 0.5843(4) 0.1098(3) 0.0796(15) Uani 1 1 d . . . . .
F4 F 1.0092(4) 0.8488(4) 0.5599(3) 0.0605(11) Uani 1 1 d . . . . .
F5 F 0.8424(4) 0.7669(5) 0.5991(3) 0.0760(15) Uani 1 1 d . . . . .
F6 F 0.8578(4) 0.9272(4) 0.4875(4) 0.0771(15) Uani 1 1 d . . . . .
F7 F 0.4010(4) 0.9374(3) 0.4789(4) 0.0661(12) Uani 1 1 d . . . . .
F8 F 0.4097(6) 0.7796(5) 0.5950(3) 0.0912(18) Uani 1 1 d . . . . .
F9 F 0.7408(6) 0.4649(5) 0.1045(3) 0.0933(19) Uani 1 1 d . . . . .
F10 F 0.0738(5) 1.2782(4) 0.1470(5) 0.106(2) Uani 1 1 d . . . . .
F11 F 0.1511(5) 1.1278(6) 0.2463(4) 0.0948(19) Uani 1 1 d . . . . .
F12 F 0.5381(4) 0.7656(4) -0.1416(3) 0.0614(11) Uani 1 1 d . . . . .
F13 F 0.3794(4) 0.7581(4) -0.1982(3) 0.0631(12) Uani 1 1 d . . . . .
F14 F 0.4977(4) 0.8907(4) -0.2720(3) 0.0657(12) Uani 1 1 d . . . . .
F15 F 0.4019(4) 0.4987(3) 0.1538(3) 0.0603(11) Uani 1 1 d . . . . .
F16 F 0.2799(4) 0.3745(3) 0.2437(3) 0.0650(12) Uani 1 1 d . . . . .
F17 F 0.2343(5) 0.4851(4) 0.1106(3) 0.0668(12) Uani 1 1 d . . . . .
F18 F -0.0195(4) 1.1222(5) 0.2021(4) 0.0863(16) Uani 1 1 d . . . . .
O1 O 0.6099(4) 0.6689(4) 0.1755(3) 0.0414(9) Uani 1 1 d . . . . .
O2 O 0.6056(4) 0.4770(4) 0.2989(3) 0.0440(10) Uani 1 1 d . . . . .
O3 O 1.0340(3) 0.8180(3) 0.3620(2) 0.0336(8) Uani 1 1 d . . . . .
O4 O 1.0271(3) 0.6317(3) 0.4929(3) 0.0380(9) Uani 1 1 d . . . . .
O5 O 0.4256(4) 0.8115(3) 0.3382(3) 0.0386(9) Uani 1 1 d . . . . .
O6 O 0.4147(3) 0.6264(3) 0.4685(3) 0.0313(7) Uani 1 1 d . . . . .
O7 O 0.4475(3) 1.0013(3) -0.1119(3) 0.0331(8) Uani 1 1 d . . . . .
O8 O 0.2898(4) 1.1427(3) 0.0574(3) 0.0425(9) Uani 1 1 d . . . . .
O9 O 0.0922(4) 1.1356(3) 0.0076(3) 0.0400(9) Uani 1 1 d . . . . .
O10 O 0.2592(4) 0.9808(3) -0.1669(3) 0.0371(9) Uani 1 1 d . . . . .
O11 O 0.2732(4) 0.5819(3) 0.3183(2) 0.0362(8) Uani 1 1 d . . . . .
O12 O 0.0816(3) 0.5757(3) 0.2589(3) 0.0365(8) Uani 1 1 d . . . . .
N1 N 0.7401(4) 0.6213(3) 0.2999(3) 0.0235(7) Uani 1 1 d . . . . .
N2 N 0.5920(3) 0.7387(3) 0.4324(3) 0.0210(7) Uani 1 1 d . . . . .
N3 N 0.8475(3) 0.7155(3) 0.4137(2) 0.0202(7) Uani 1 1 d . . . . .
N4 N 0.3166(3) 0.8466(3) -0.0179(2) 0.0223(7) Uani 1 1 d . . . . .
C16 C 0.4017(4) 0.7988(4) 0.0533(3) 0.0220(8) Uani 1 1 d . . . . .
H18 H 0.4647 0.8533 0.0418 0.026 Uiso 1 1 calc R U . . .
H17 H 0.4434 0.7209 0.0467 0.026 Uiso 1 1 calc R U . . .
N6 N 0.1840(3) 0.9625(3) 0.1193(3) 0.0227(7) Uani 1 1 d . . . . .
C1 C 0.7876(7) 0.5047(6) 0.1611(5) 0.0529(16) Uani 1 1 d . . . . .
C2 C 0.7887(4) 0.5420(4) 0.3843(3) 0.0240(8) Uani 1 1 d . . . . .
H10 H 0.8744 0.5112 0.3655 0.029 Uiso 1 1 calc R U . . .
H9 H 0.7401 0.4737 0.4113 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7834(4) 0.6086(3) 0.4596(3) 0.0200(8) Uani 1 1 d . . . . .
H8 H 0.8282 0.5568 0.5113 0.024 Uiso 1 1 calc R U . . .
C4 C 0.6540(4) 0.6471(4) 0.5045(3) 0.0225(8) Uani 1 1 d . . . . .
H2 H 0.6066 0.5778 0.5295 0.027 Uiso 1 1 calc R U . . .
H1 H 0.6584 0.6792 0.5581 0.027 Uiso 1 1 calc R U . . .
C5 C 0.3741(6) 0.8277(6) 0.5103(5) 0.0492(15) Uani 1 1 d . . . . .
C6 C 0.9155(5) 0.8257(6) 0.5272(4) 0.0407(13) Uani 1 1 d . . . . .
C7 C 0.7874(4) 0.7984(4) 0.3356(3) 0.0213(8) Uani 1 1 d . . . . .
H5 H 0.8344 0.8687 0.3079 0.026 Uiso 1 1 calc R U . . .
C8 C 0.6590(4) 0.8397(4) 0.3778(3) 0.0243(9) Uani 1 1 d . . . . .
H4 H 0.6640 0.8896 0.4198 0.029 Uiso 1 1 calc R U . . .
H3 H 0.6143 0.8885 0.3260 0.029 Uiso 1 1 calc R U . . .
C9 C 0.7929(4) 0.7341(4) 0.2588(3) 0.0237(8) Uani 1 1 d . . . . .
H6 H 0.7472 0.7847 0.2082 0.028 Uiso 1 1 calc R U . . .
H7 H 0.8789 0.7190 0.2298 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3301(4) 0.7851(4) 0.1538(3) 0.0222(8) Uani 1 1 d . . . . .
H19 H 0.3855 0.7397 0.2003 0.027 Uiso 1 1 calc R U . . .
C11 C 0.2786(4) 0.9013(4) 0.1785(3) 0.0230(8) Uani 1 1 d . . . . .
H20 H 0.2427 0.8851 0.2466 0.028 Uiso 1 1 calc R U . . .
H21 H 0.3450 0.9522 0.1670 0.028 Uiso 1 1 calc R U . . .
C12 C 0.0901(7) 1.1627(7) 0.1735(6) 0.062(2) Uani 1 1 d . . . . .
C13 C 0.4495(5) 0.8304(5) -0.1874(3) 0.0347(11) Uani 1 1 d . . . . .
C14 C 0.2064(4) 0.7869(4) -0.0025(3) 0.0231(8) Uani 1 1 d . . . . .
H16 H 0.2293 0.7073 -0.0135 0.028 Uiso 1 1 calc R U . . .
H15 H 0.1515 0.8331 -0.0482 0.028 Uiso 1 1 calc R U . . .
C15 C 0.1402(4) 0.7752(4) 0.0984(3) 0.0206(8) Uani 1 1 d . . . . .
H12 H 0.0727 0.7243 0.1100 0.025 Uiso 1 1 calc R U . . .
N5 N 0.2274(3) 0.7153(3) 0.1647(3) 0.0235(7) Uani 1 1 d . . . . .
C17 C 0.2853(6) 0.4807(4) 0.1844(4) 0.0406(13) Uani 1 1 d . . . . .
C18 C 0.0856(4) 0.8925(4) 0.1212(3) 0.0228(8) Uani 1 1 d . . . . .
H14 H 0.0326 0.9381 0.0739 0.027 Uiso 1 1 calc R U . . .
H13 H 0.0348 0.8764 0.1848 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.416(4) . ?
S1 O2 1.422(4) . ?
S1 N1 1.587(4) . ?
S1 C1 1.834(6) . ?
S2 O6 1.412(3) . ?
S2 O5 1.419(4) . ?
S2 N2 1.577(4) . ?
S2 C5 1.830(6) . ?
S3 O4 1.409(3) . ?
S3 O3 1.424(3) . ?
S3 N3 1.594(4) . ?
S3 C6 1.824(5) . ?
S4 O7 1.407(4) . ?
S4 O10 1.427(4) . ?
S4 N4 1.586(4) . ?
S4 C13 1.834(5) . ?
S5 O9 1.421(4) . ?
S5 O8 1.425(4) . ?
S5 N6 1.588(4) . ?
S5 C12 1.820(7) . ?
S6 O12 1.418(4) . ?
S6 O11 1.420(4) . ?
S6 N5 1.596(4) . ?
S6 C17 1.824(5) . ?
F1 C1 1.322(9) . ?
F2 C5 1.298(8) . ?
F3 C1 1.330(8) . ?
F4 C6 1.333(6) . ?
F5 C6 1.310(7) . ?
F6 C6 1.307(8) . ?
F7 C5 1.312(7) . ?
F8 C5 1.334(9) . ?
F9 C1 1.297(8) . ?
F10 C12 1.305(9) . ?
F11 C12 1.323(9) . ?
F12 C13 1.326(7) . ?
F13 C13 1.311(6) . ?
F14 C13 1.316(6) . ?
F15 C17 1.328(7) . ?
F16 C17 1.315(6) . ?
F17 C17 1.316(7) . ?
F18 C12 1.337(9) . ?
N1 C9 1.466(5) . ?
N1 C2 1.477(5) . ?
N2 C8 1.465(5) . ?
N2 C4 1.480(5) . ?
N3 C3 1.479(5) . ?
N3 C7 1.484(5) . ?
N4 C14 1.467(6) . ?
N4 C16 1.491(5) . ?
C16 C10 1.532(6) . ?
C16 H18 0.9900 . ?
C16 H17 0.9900 . ?
N6 C18 1.473(5) . ?
N6 C11 1.476(5) . ?
C2 C3 1.534(6) . ?
C2 H10 0.9900 . ?
C2 H9 0.9900 . ?
C3 C4 1.535(6) . ?
C3 H8 1.0000 . ?
C4 H2 0.9900 . ?
C4 H1 0.9900 . ?
C7 C8 1.522(6) . ?
C7 C9 1.533(6) . ?
C7 H5 1.0000 . ?
C8 H4 0.9900 . ?
C8 H3 0.9900 . ?
C9 H6 0.9900 . ?
C9 H7 0.9900 . ?
C10 N5 1.479(6) . ?
C10 C11 1.526(6) . ?
C10 H19 1.0000 . ?
C11 H20 0.9900 . ?
C11 H21 0.9900 . ?
C14 C15 1.519(6) . ?
C14 H16 0.9900 . ?
C14 H15 0.9900 . ?
C15 N5 1.477(5) . ?
C15 C18 1.533(6) . ?
C15 H12 1.0000 . ?
C18 H14 0.9900 . ?
C18 H13 0.9900 . ?

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
O1 S1 O2 121.7(3) . . ?
O1 S1 N1 109.8(2) . . ?
O2 S1 N1 109.3(2) . . ?
O1 S1 C1 104.5(3) . . ?
O2 S1 C1 104.5(3) . . ?
N1 S1 C1 105.6(3) . . ?
O6 S2 O5 122.1(2) . . ?
O6 S2 N2 110.3(2) . . ?
O5 S2 N2 109.5(2) . . ?
O6 S2 C5 105.2(3) . . ?
O5 S2 C5 103.9(3) . . ?
N2 S2 C5 104.1(3) . . ?
O4 S3 O3 122.9(2) . . ?
O4 S3 N3 109.6(2) . . ?
O3 S3 N3 109.5(2) . . ?
O4 S3 C6 105.0(3) . . ?
O3 S3 C6 104.4(3) . . ?
N3 S3 C6 103.4(2) . . ?
O7 S4 O10 121.7(2) . . ?
O7 S4 N4 110.5(2) . . ?
O10 S4 N4 109.4(2) . . ?
O7 S4 C13 104.6(2) . . ?
O10 S4 C13 104.3(3) . . ?
N4 S4 C13 104.8(2) . . ?
O9 S5 O8 121.9(3) . . ?
O9 S5 N6 109.6(2) . . ?
O8 S5 N6 109.4(2) . . ?
O9 S5 C12 104.5(3) . . ?
O8 S5 C12 104.5(3) . . ?
N6 S5 C12 105.6(3) . . ?
O12 S6 O11 123.0(2) . . ?
O12 S6 N5 108.8(2) . . ?
O11 S6 N5 109.9(2) . . ?
O12 S6 C17 104.8(3) . . ?
O11 S6 C17 104.6(3) . . ?
N5 S6 C17 104.1(2) . . ?
C9 N1 C2 115.9(3) . . ?
C9 N1 S1 120.0(3) . . ?
C2 N1 S1 121.3(3) . . ?
C8 N2 C4 116.8(3) . . ?
C8 N2 S2 120.7(3) . . ?
C4 N2 S2 121.4(3) . . ?
C3 N3 C7 112.5(3) . . ?
C3 N3 S3 124.6(3) . . ?
C7 N3 S3 122.8(3) . . ?
C14 N4 C16 117.0(3) . . ?
C14 N4 S4 120.3(3) . . ?
C16 N4 S4 120.3(3) . . ?
N4 C16 C10 109.7(3) . . ?
N4 C16 H18 109.7 . . ?
C10 C16 H18 109.7 . . ?
N4 C16 H17 109.7 . . ?
C10 C16 H17 109.7 . . ?
H18 C16 H17 108.2 . . ?
C18 N6 C11 116.0(3) . . ?
C18 N6 S5 121.3(3) . . ?
C11 N6 S5 121.1(3) . . ?
F9 C1 F1 109.3(6) . . ?
F9 C1 F3 109.2(6) . . ?
F1 C1 F3 107.7(7) . . ?
F9 C1 S1 111.6(6) . . ?
F1 C1 S1 109.6(5) . . ?
F3 C1 S1 109.4(4) . . ?
N1 C2 C3 110.5(3) . . ?
N1 C2 H10 109.6 . . ?
C3 C2 H10 109.6 . . ?
N1 C2 H9 109.6 . . ?
C3 C2 H9 109.6 . . ?
H10 C2 H9 108.1 . . ?
N3 C3 C2 107.6(3) . . ?
N3 C3 C4 108.6(3) . . ?
C2 C3 C4 114.9(4) . . ?
N3 C3 H8 108.6 . . ?
C2 C3 H8 108.6 . . ?
C4 C3 H8 108.6 . . ?
N2 C4 C3 109.8(3) . . ?
N2 C4 H2 109.7 . . ?
C3 C4 H2 109.7 . . ?
N2 C4 H1 109.7 . . ?
C3 C4 H1 109.7 . . ?
H2 C4 H1 108.2 . . ?
F2 C5 F7 108.6(6) . . ?
F2 C5 F8 109.0(6) . . ?
F7 C5 F8 109.0(6) . . ?
F2 C5 S2 110.6(5) . . ?
F7 C5 S2 110.5(4) . . ?
F8 C5 S2 109.1(4) . . ?
F6 C6 F5 109.6(6) . . ?
F6 C6 F4 107.6(5) . . ?
F5 C6 F4 108.6(5) . . ?
F6 C6 S3 110.6(4) . . ?
F5 C6 S3 110.1(4) . . ?
F4 C6 S3 110.4(4) . . ?
N3 C7 C8 108.1(3) . . ?
N3 C7 C9 107.7(3) . . ?
C8 C7 C9 114.8(4) . . ?
N3 C7 H5 108.7 . . ?
C8 C7 H5 108.7 . . ?
C9 C7 H5 108.7 . . ?
N2 C8 C7 111.0(3) . . ?
N2 C8 H4 109.4 . . ?
C7 C8 H4 109.4 . . ?
N2 C8 H3 109.4 . . ?
C7 C8 H3 109.4 . . ?
H4 C8 H3 108.0 . . ?
N1 C9 C7 110.4(3) . . ?
N1 C9 H6 109.6 . . ?
C7 C9 H6 109.6 . . ?
N1 C9 H7 109.6 . . ?
C7 C9 H7 109.6 . . ?
H6 C9 H7 108.1 . . ?
N5 C10 C11 108.4(3) . . ?
N5 C10 C16 108.4(3) . . ?
C11 C10 C16 114.9(4) . . ?
N5 C10 H19 108.3 . . ?
C11 C10 H19 108.3 . . ?
C16 C10 H19 108.3 . . ?
N6 C11 C10 109.3(3) . . ?
N6 C11 H20 109.8 . . ?
C10 C11 H20 109.8 . . ?
N6 C11 H21 109.8 . . ?
C10 C11 H21 109.8 . . ?
H20 C11 H21 108.3 . . ?
F10 C12 F11 109.5(6) . . ?
F10 C12 F18 108.4(6) . . ?
F11 C12 F18 108.2(8) . . ?
F10 C12 S5 111.5(7) . . ?
F11 C12 S5 109.9(5) . . ?
F18 C12 S5 109.3(4) . . ?
F13 C13 F14 108.4(5) . . ?
F13 C13 F12 107.9(5) . . ?
F14 C13 F12 109.2(5) . . ?
F13 C13 S4 110.8(4) . . ?
F14 C13 S4 110.7(4) . . ?
F12 C13 S4 109.8(3) . . ?
N4 C14 C15 110.1(3) . . ?
N4 C14 H16 109.6 . . ?
C15 C14 H16 109.6 . . ?
N4 C14 H15 109.6 . . ?
C15 C14 H15 109.6 . . ?
H16 C14 H15 108.2 . . ?
N5 C15 C14 108.4(4) . . ?
N5 C15 C18 107.9(3) . . ?
C14 C15 C18 115.0(3) . . ?
N5 C15 H12 108.4 . . ?
C14 C15 H12 108.4 . . ?
C18 C15 H12 108.4 . . ?
C15 N5 C10 112.4(3) . . ?
C15 N5 S6 123.1(3) . . ?
C10 N5 S6 124.4(3) . . ?
F16 C17 F17 108.9(5) . . ?
F16 C17 F15 108.8(5) . . ?
F17 C17 F15 108.1(5) . . ?
F16 C17 S6 110.2(4) . . ?
F17 C17 S6 110.3(4) . . ?
F15 C17 S6 110.4(4) . . ?
N6 C18 C15 110.1(3) . . ?
N6 C18 H14 109.6 . . ?
C15 C18 H14 109.6 . . ?
N6 C18 H13 109.6 . . ?
C15 C18 H13 109.6 . . ?
H14 C18 H13 108.2 . . ?

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
O1 S1 N1 C9 -32.1(4) . . . . ?
O2 S1 N1 C9 -168.1(4) . . . . ?
C1 S1 N1 C9 80.0(4) . . . . ?
O1 S1 N1 C2 167.4(4) . . . . ?
O2 S1 N1 C2 31.5(4) . . . . ?
C1 S1 N1 C2 -80.5(4) . . . . ?
O6 S2 N2 C8 167.0(3) . . . . ?
O5 S2 N2 C8 30.0(4) . . . . ?
C5 S2 N2 C8 -80.6(4) . . . . ?
O6 S2 N2 C4 -25.2(4) . . . . ?
O5 S2 N2 C4 -162.2(3) . . . . ?
C5 S2 N2 C4 87.3(4) . . . . ?
O4 S3 N3 C3 17.6(4) . . . . ?
O3 S3 N3 C3 155.2(3) . . . . ?
C6 S3 N3 C3 -93.9(4) . . . . ?
O4 S3 N3 C7 -160.1(3) . . . . ?
O3 S3 N3 C7 -22.5(4) . . . . ?
C6 S3 N3 C7 88.3(4) . . . . ?
O7 S4 N4 C14 164.8(3) . . . . ?
O10 S4 N4 C14 28.2(4) . . . . ?
C13 S4 N4 C14 -83.1(4) . . . . ?
O7 S4 N4 C16 -33.3(4) . . . . ?
O10 S4 N4 C16 -169.8(3) . . . . ?
C13 S4 N4 C16 78.9(4) . . . . ?
C14 N4 C16 C10 -50.0(5) . . . . ?
S4 N4 C16 C10 147.4(3) . . . . ?
O9 S5 N6 C18 -26.7(4) . . . . ?
O8 S5 N6 C18 -162.8(4) . . . . ?
C12 S5 N6 C18 85.3(4) . . . . ?
O9 S5 N6 C11 168.1(4) . . . . ?
O8 S5 N6 C11 32.1(4) . . . . ?
C12 S5 N6 C11 -79.9(4) . . . . ?
O1 S1 C1 F9 -61.9(6) . . . . ?
O2 S1 C1 F9 67.0(6) . . . . ?
N1 S1 C1 F9 -177.7(5) . . . . ?
O1 S1 C1 F1 176.9(5) . . . . ?
O2 S1 C1 F1 -54.2(6) . . . . ?
N1 S1 C1 F1 61.1(6) . . . . ?
O1 S1 C1 F3 59.0(6) . . . . ?
O2 S1 C1 F3 -172.0(5) . . . . ?
N1 S1 C1 F3 -56.8(6) . . . . ?
C9 N1 C2 C3 51.9(5) . . . . ?
S1 N1 C2 C3 -146.8(3) . . . . ?
C7 N3 C3 C2 62.7(4) . . . . ?
S3 N3 C3 C2 -115.3(3) . . . . ?
C7 N3 C3 C4 -62.2(4) . . . . ?
S3 N3 C3 C4 119.9(3) . . . . ?
N1 C2 C3 N3 -54.2(4) . . . . ?
N1 C2 C3 C4 66.8(5) . . . . ?
C8 N2 C4 C3 -50.5(5) . . . . ?
S2 N2 C4 C3 141.3(3) . . . . ?
N3 C3 C4 N2 53.3(4) . . . . ?
C2 C3 C4 N2 -67.2(4) . . . . ?
O6 S2 C5 F2 -58.7(6) . . . . ?
O5 S2 C5 F2 70.6(6) . . . . ?
N2 S2 C5 F2 -174.8(5) . . . . ?
O6 S2 C5 F7 -179.0(5) . . . . ?
O5 S2 C5 F7 -49.6(6) . . . . ?
N2 S2 C5 F7 64.9(5) . . . . ?
O6 S2 C5 F8 61.2(5) . . . . ?
O5 S2 C5 F8 -169.5(5) . . . . ?
N2 S2 C5 F8 -54.9(5) . . . . ?
O4 S3 C6 F6 -178.4(4) . . . . ?
O3 S3 C6 F6 51.1(5) . . . . ?
N3 S3 C6 F6 -63.4(4) . . . . ?
O4 S3 C6 F5 -57.1(5) . . . . ?
O3 S3 C6 F5 172.3(4) . . . . ?
N3 S3 C6 F5 57.8(5) . . . . ?
O4 S3 C6 F4 62.8(5) . . . . ?
O3 S3 C6 F4 -67.8(5) . . . . ?
N3 S3 C6 F4 177.7(4) . . . . ?
C3 N3 C7 C8 61.8(4) . . . . ?
S3 N3 C7 C8 -120.2(4) . . . . ?
C3 N3 C7 C9 -62.8(4) . . . . ?
S3 N3 C7 C9 115.2(4) . . . . ?
C4 N2 C8 C7 50.9(5) . . . . ?
S2 N2 C8 C7 -140.7(3) . . . . ?
N3 C7 C8 N2 -53.3(5) . . . . ?
C9 C7 C8 N2 66.9(5) . . . . ?
C2 N1 C9 C7 -52.0(5) . . . . ?
S1 N1 C9 C7 146.5(3) . . . . ?
N3 C7 C9 N1 54.4(4) . . . . ?
C8 C7 C9 N1 -66.1(4) . . . . ?
N4 C16 C10 N5 52.5(4) . . . . ?
N4 C16 C10 C11 -68.9(5) . . . . ?
C18 N6 C11 C10 53.2(5) . . . . ?
S5 N6 C11 C10 -140.9(3) . . . . ?
N5 C10 C11 N6 -55.1(4) . . . . ?
C16 C10 C11 N6 66.3(5) . . . . ?
O9 S5 C12 F10 -64.2(6) . . . . ?
O8 S5 C12 F10 64.9(6) . . . . ?
N6 S5 C12 F10 -179.7(5) . . . . ?
O9 S5 C12 F11 174.3(6) . . . . ?
O8 S5 C12 F11 -56.7(7) . . . . ?
N6 S5 C12 F11 58.7(6) . . . . ?
O9 S5 C12 F18 55.7(6) . . . . ?
O8 S5 C12 F18 -175.3(5) . . . . ?
N6 S5 C12 F18 -59.9(6) . . . . ?
O7 S4 C13 F13 179.3(4) . . . . ?
O10 S4 C13 F13 -51.9(4) . . . . ?
N4 S4 C13 F13 63.0(4) . . . . ?
O7 S4 C13 F14 -60.5(5) . . . . ?
O10 S4 C13 F14 68.4(5) . . . . ?
N4 S4 C13 F14 -176.7(4) . . . . ?
O7 S4 C13 F12 60.2(4) . . . . ?
O10 S4 C13 F12 -171.0(4) . . . . ?
N4 S4 C13 F12 -56.1(4) . . . . ?
C16 N4 C14 C15 51.0(5) . . . . ?
S4 N4 C14 C15 -146.5(3) . . . . ?
N4 C14 C15 N5 -54.4(4) . . . . ?
N4 C14 C15 C18 66.5(5) . . . . ?
C14 C15 N5 C10 63.2(4) . . . . ?
C18 C15 N5 C10 -61.9(4) . . . . ?
C14 C15 N5 S6 -120.5(4) . . . . ?
C18 C15 N5 S6 114.4(4) . . . . ?
C11 C10 N5 C15 63.0(4) . . . . ?
C16 C10 N5 C15 -62.4(4) . . . . ?
C11 C10 N5 S6 -113.3(4) . . . . ?
C16 C10 N5 S6 121.3(4) . . . . ?
O12 S6 N5 C15 -19.1(4) . . . . ?
O11 S6 N5 C15 -156.3(3) . . . . ?
C17 S6 N5 C15 92.2(4) . . . . ?
O12 S6 N5 C10 156.8(4) . . . . ?
O11 S6 N5 C10 19.6(4) . . . . ?
C17 S6 N5 C10 -91.9(4) . . . . ?
O12 S6 C17 F16 -68.6(5) . . . . ?
O11 S6 C17 F16 61.9(5) . . . . ?
N5 S6 C17 F16 177.2(4) . . . . ?
O12 S6 C17 F17 51.7(4) . . . . ?
O11 S6 C17 F17 -177.8(4) . . . . ?
N5 S6 C17 F17 -62.5(4) . . . . ?
O12 S6 C17 F15 171.1(4) . . . . ?
O11 S6 C17 F15 -58.3(5) . . . . ?
N5 S6 C17 F15 57.0(5) . . . . ?
C11 N6 C18 C15 -52.9(5) . . . . ?
S5 N6 C18 C15 141.2(3) . . . . ?
N5 C15 C18 N6 54.1(4) . . . . ?
C14 C15 C18 N6 -67.1(4) . . . . ?

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
C18 H13 O3 0.99 2.52 3.389(6) 146.0 1_455
C18 H14 O9 0.99 2.42 3.131(6) 128.6 2_575
C11 H21 O7 0.99 2.41 3.322(6) 153.1 2_675
C10 H19 O5 1.00 2.57 3.240(6) 124.0 .
C10 H19 O1 1.00 2.52 3.260(6) 130.9 .
C9 H7 O12 0.99 2.64 3.479(6) 142.3 1_655
C7 H5 O10 1.00 2.61 3.117(5) 111.7 2_675
C4 H2 O6 0.99 2.46 3.344(6) 148.3 2_666
C3 H8 O4 1.00 2.56 3.264(5) 127.6 2_766
C2 H9 O6 0.99 2.42 3.314(6) 149.9 2_666
C2 H10 O12 0.99 2.64 3.473(6) 142.4 1_655
C2 H10 O4 0.99 2.60 3.130(5) 113.3 2_766
C16 H18 O7 0.99 2.64 3.500(6) 144.9 2_675
C18 H13 O3 0.99 2.52 3.389(6) 146.0 1_455
C18 H14 O9 0.99 2.42 3.131(6) 128.6 2_575
C11 H21 O7 0.99 2.41 3.322(6) 153.1 2_675
C10 H19 O5 1.00 2.57 3.240(6) 124.0 .
C10 H19 O1 1.00 2.52 3.260(6) 130.9 .
C9 H7 O12 0.99 2.64 3.479(6) 142.3 1_655
C7 H5 O10 1.00 2.61 3.117(5) 111.7 2_675
C4 H2 O6 0.99 2.46 3.344(6) 148.3 2_666
C3 H8 O4 1.00 2.56 3.264(5) 127.6 2_766
C2 H9 O6 0.99 2.42 3.314(6) 149.9 2_666
C2 H10 O12 0.99 2.64 3.473(6) 142.4 1_655
C2 H10 O4 0.99 2.60 3.130(5) 113.3 2_766
C16 H18 O7 0.99 2.64 3.500(6) 144.9 2_675
C18 H13 O3 0.99 2.52 3.389(6) 146.0 1_455
C18 H14 O9 0.99 2.42 3.131(6) 128.6 2_575
C11 H21 O7 0.99 2.41 3.322(6) 153.1 2_675
C10 H19 O5 1.00 2.57 3.240(6) 124.0 .
C10 H19 O1 1.00 2.52 3.260(6) 130.9 .
C9 H7 O12 0.99 2.64 3.479(6) 142.3 1_655
C7 H5 O10 1.00 2.61 3.117(5) 111.7 2_675
C4 H2 O6 0.99 2.46 3.344(6) 148.3 2_666
C3 H8 O4 1.00 2.56 3.264(5) 127.6 2_766
C2 H9 O6 0.99 2.42 3.314(6) 149.9 2_666
C2 H10 O12 0.99 2.64 3.473(6) 142.4 1_655
C2 H10 O4 0.99 2.60 3.130(5) 113.3 2_766
C16 H18 O7 0.99 2.64 3.500(6) 144.9 2_675
C2 H10 O4 0.99 2.60 3.130(5) 113.3 2_766
C2 H10 O12 0.99 2.64 3.473(6) 142.4 1_655
C2 H9 O6 0.99 2.42 3.314(6) 149.9 2_666
C3 H8 O4 1.00 2.56 3.264(5) 127.6 2_766
C4 H2 O6 0.99 2.46 3.344(6) 148.3 2_666
C7 H5 O10 1.00 2.61 3.117(5) 111.7 2_675
C9 H7 O12 0.99 2.64 3.479(6) 142.3 1_655
C10 H19 O1 1.00 2.52 3.260(6) 130.9 .
C10 H19 O5 1.00 2.57 3.240(6) 124.0 .
C11 H21 O7 0.99 2.41 3.322(6) 153.1 2_675
C18 H14 O9 0.99 2.42 3.131(6) 128.6 2_575
C18 H13 O3 0.99 2.52 3.389(6) 146.0 1_455

_refine_diff_density_max         1.486
_refine_diff_density_min         -1.469
_refine_diff_density_rms         0.311

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_mo_Astakhova_bak_0m
_database_code_depnum_ccdc_archive 'CCDC 1520698'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
3,7-diiodo-1,5-bis[(trifluoromethyl)sulfonyl]-1,5-diazocane
_chemical_name_common            ?
_chemical_melting_point          426
_chemical_formula_moiety         'C8 H10 F6 I2 N2 O4 S2'
_chemical_formula_sum            'C8 H10 F6 I2 N2 O4 S2'
_chemical_formula_weight         630.10

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'
I I -0.4742 1.8119 '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                   11.3052(16)
_cell_length_b                   17.982(3)
_cell_length_c                   18.058(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.155(5)
_cell_angle_gamma                90
_cell_volume                     3613.5(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    200
_cell_measurement_theta_min      5
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.316
_exptl_crystal_F_000             2368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.786
_shelx_estimated_absorpt_T_min   0.253
_shelx_estimated_absorpt_T_max   0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3628
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            147899
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.152
_diffrn_reflns_theta_max         30.150
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10609
_reflns_number_gt                7308
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0361P)²+11.1751P] 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     SHELXL
_refine_ls_extinction_coef       0.00110(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10609
_refine_ls_number_parameters     434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.47960(3) 0.88808(2) -0.05984(2) 0.04694(11) Uani 1 1 d . . . . .
I2 I 0.72407(4) 0.65172(2) 0.29080(2) 0.04192(10) Uani 1 1 d . . . . .
I3 I 0.90443(4) 0.30315(2) 0.62543(2) 0.04487(11) Uani 1 1 d . . . . .
I4 I 0.82437(3) 0.02848(2) 0.94450(2) 0.03852(10) Uani 1 1 d . . . . .
S1 S 0.83546(10) 0.90536(6) 0.17285(6) 0.0253(2) Uani 1 1 d . . . . .
S2 S 0.85602(9) 0.71543(6) 0.03168(6) 0.0268(2) Uani 1 1 d . . . . .
S3 S 0.56950(10) 0.11976(6) 0.68816(7) 0.0301(2) Uani 1 1 d . . . . .
S4 S 0.67659(10) 0.29847(7) 0.85257(6) 0.0304(2) Uani 1 1 d . . . . .
F1 F 0.9001(3) 1.02362(18) 0.2524(2) 0.0577(9) Uani 1 1 d . . . . .
F2 F 0.7519(3) 0.6466(2) -0.08962(18) 0.0611(10) Uani 1 1 d . . . . .
F3 F 0.8069(4) 0.57508(19) 0.0045(2) 0.0660(10) Uani 1 1 d . . . . .
F4 F 0.7712(3) 0.95595(17) 0.29571(17) 0.0510(8) Uani 1 1 d . . . . .
F5 F 0.7146(3) 1.02352(18) 0.1988(2) 0.0624(10) Uani 1 1 d . . . . .
F6 F 0.9383(3) 0.6199(2) -0.0556(2) 0.0667(11) Uani 1 1 d . . . . .
F7 F 0.6469(5) 0.0345(3) 0.5889(3) 0.117(2) Uani 1 1 d . . . . .
F8 F 0.6664(4) 0.4068(2) 0.9462(2) 0.0825(14) Uani 1 1 d . . . . .
F9 F 0.8113(3) 0.33155(18) 0.98217(16) 0.0500(8) Uani 1 1 d . . . . .
F10 F 0.5573(4) -0.02365(19) 0.6597(2) 0.0773(12) Uani 1 1 d . . . . .
F11 F 0.4557(5) 0.0423(2) 0.5762(3) 0.121(2) Uani 1 1 d . . . . .
F12 F 0.8243(4) 0.40899(18) 0.89507(19) 0.0621(10) Uani 1 1 d . . . . .
O1 O 0.9291(3) 0.86503(19) 0.2189(2) 0.0369(8) Uani 1 1 d . . . . .
O2 O 0.8521(3) 0.9402(2) 0.10519(19) 0.0399(8) Uani 1 1 d . . . . .
O3 O 0.8731(3) 0.7762(2) -0.01528(19) 0.0411(8) Uani 1 1 d . . . . .
O4 O 0.9448(3) 0.6929(2) 0.09356(18) 0.0380(8) Uani 1 1 d . . . . .
O5 O 0.6314(3) 0.3430(2) 0.78871(19) 0.0427(9) Uani 1 1 d . . . . .
O6 O 0.6001(3) 0.2564(2) 0.8917(2) 0.0471(9) Uani 1 1 d . . . . .
O7 O 0.5334(3) 0.1810(2) 0.6404(2) 0.0548(11) Uani 1 1 d . . . . .
O8 O 0.5077(3) 0.0971(2) 0.7467(2) 0.0439(9) Uani 1 1 d . . . . .
C2 C 0.6292(4) 0.7628(2) 0.0101(2) 0.0266(9) Uani 1 1 d . . . . .
H2 H 0.5524 0.7432 0.0211 0.032 Uiso 1 1 calc R U . . .
H1 H 0.6327 0.7509 -0.0430 0.032 Uiso 1 1 calc R U . . .
N2 N 0.7298(3) 0.72451(19) 0.05919(18) 0.0230(7) Uani 1 1 d . . . . .
N3 N 0.7097(3) 0.1268(2) 0.72070(19) 0.0244(7) Uani 1 1 d . . . . .
N4 N 0.7808(3) 0.24598(18) 0.83379(18) 0.0218(7) Uani 1 1 d . . . . .
C1 C 0.8025(5) 0.9817(3) 0.2339(3) 0.0349(11) Uani 1 1 d . . . . .
N1 N 0.7172(3) 0.85521(19) 0.15777(19) 0.0235(7) Uani 1 1 d . . . . .
C3 C 0.6172(4) 0.8766(3) 0.0962(2) 0.0295(9) Uani 1 1 d . . . . .
H4 H 0.6125 0.9315 0.0933 0.035 Uiso 1 1 calc R U . . .
H3 H 0.5405 0.8583 0.1088 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6305(4) 0.8464(2) 0.0195(2) 0.0257(9) Uani 1 1 d . . . . .
H10 H 0.7063 0.8664 0.0059 0.031 Uiso 1 1 calc R U . . .
C5 C 0.8364(5) 0.6341(3) -0.0314(3) 0.0417(12) Uani 1 1 d . . . . .
C6 C 0.6982(4) 0.7971(2) 0.2127(2) 0.0266(9) Uani 1 1 d . . . . .
H5 H 0.6107 0.7893 0.2096 0.032 Uiso 1 1 calc R U . . .
H6 H 0.7310 0.8149 0.2641 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7565(4) 0.7232(2) 0.2000(2) 0.0248(9) Uani 1 1 d . . . . .
H7 H 0.8450 0.7307 0.2041 0.030 Uiso 1 1 calc R U . . .
C8 C 0.7089(4) 0.6830(2) 0.1271(2) 0.0268(9) Uani 1 1 d . . . . .
H9 H 0.7481 0.6337 0.1279 0.032 Uiso 1 1 calc R U . . .
H8 H 0.6215 0.6747 0.1237 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5553(5) 0.0393(3) 0.6238(3) 0.0425(12) Uani 1 1 d . . . . .
C10 C 0.7870(4) 0.1690(2) 0.6773(2) 0.0269(9) Uani 1 1 d . . . . .
H17 H 0.7553 0.1632 0.6229 0.032 Uiso 1 1 calc R U . . .
H16 H 0.8691 0.1478 0.6874 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7935(4) 0.2516(2) 0.6968(2) 0.0252(9) Uani 1 1 d . . . . .
H18 H 0.7109 0.2734 0.6856 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8511(4) 0.2712(2) 0.7768(2) 0.0232(8) Uani 1 1 d . . . . .
H20 H 0.9321 0.2485 0.7879 0.028 Uiso 1 1 calc R U . . .
H19 H 0.8612 0.3258 0.7807 0.028 Uiso 1 1 calc R U . . .
C13 C 0.7492(5) 0.3657(3) 0.9233(3) 0.0400(12) Uani 1 1 d . . . . .
C14 C 0.7641(4) 0.0784(2) 0.7849(2) 0.0276(9) Uani 1 1 d . . . . .
H11 H 0.8499 0.0702 0.7825 0.033 Uiso 1 1 calc R U . . .
H15 H 0.7235 0.0294 0.7797 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7545(4) 0.1110(2) 0.8608(2) 0.0267(9) Uani 1 1 d . . . . .
H14 H 0.6677 0.1195 0.8628 0.032 Uiso 1 1 calc R U . . .
C16 C 0.8233(4) 0.1821(2) 0.8840(2) 0.0255(9) Uani 1 1 d . . . . .
H12 H 0.8147 0.1949 0.9361 0.031 Uiso 1 1 calc R U . . .
H13 H 0.9097 0.1737 0.8836 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.159(4) . ?
I2 C7 2.165(4) . ?
I3 C11 2.160(4) . ?
I4 C15 2.165(4) . ?
S1 O2 1.415(3) . ?
S1 O1 1.424(3) . ?
S1 N1 1.596(4) . ?
S1 C1 1.840(5) . ?
S2 O3 1.417(4) . ?
S2 O4 1.423(3) . ?
S2 N2 1.600(4) . ?
S2 C5 1.843(5) . ?
S3 O7 1.414(4) . ?
S3 O8 1.425(4) . ?
S3 N3 1.596(4) . ?
S3 C9 1.844(5) . ?
S4 O5 1.422(4) . ?
S4 O6 1.426(4) . ?
S4 N4 1.592(3) . ?
S4 C13 1.843(5) . ?
F1 C1 1.329(6) . ?
F2 C5 1.309(6) . ?
F3 C5 1.317(7) . ?
F4 C1 1.313(6) . ?
F5 C1 1.316(6) . ?
F6 C5 1.327(6) . ?
F7 C9 1.306(7) . ?
F8 C13 1.316(6) . ?
F9 C13 1.318(6) . ?
F10 C9 1.303(6) . ?
F11 C9 1.292(6) . ?
F12 C13 1.319(7) . ?
C2 N2 1.482(5) . ?
C2 C4 1.512(6) . ?
C2 H2 0.9900 . ?
C2 H1 0.9900 . ?
N2 C8 1.490(5) . ?
N3 C10 1.482(5) . ?
N3 C14 1.492(5) . ?
N4 C12 1.478(5) . ?
N4 C16 1.489(5) . ?
N1 C6 1.482(5) . ?
N1 C3 1.490(5) . ?
C3 C4 1.519(6) . ?
C3 H4 0.9900 . ?
C3 H3 0.9900 . ?
C4 H10 1.0000 . ?
C6 C7 1.519(6) . ?
C6 H5 0.9900 . ?
C6 H6 0.9900 . ?
C7 C8 1.514(6) . ?
C7 H7 1.0000 . ?
C8 H9 0.9900 . ?
C8 H8 0.9900 . ?
C10 C11 1.525(6) . ?
C10 H17 0.9900 . ?
C10 H16 0.9900 . ?
C11 C12 1.517(6) . ?
C11 H18 1.0000 . ?
C12 H20 0.9900 . ?
C12 H19 0.9900 . ?
C14 C15 1.512(6) . ?
C14 H11 0.9900 . ?
C14 H15 0.9900 . ?
C15 C16 1.518(6) . ?
C15 H14 1.0000 . ?
C16 H12 0.9900 . ?
C16 H13 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 122.1(2) . . ?
O2 S1 N1 109.8(2) . . ?
O1 S1 N1 109.00(19) . . ?
O2 S1 C1 105.0(2) . . ?
O1 S1 C1 103.8(2) . . ?
N1 S1 C1 105.8(2) . . ?
O3 S2 O4 122.5(2) . . ?
O3 S2 N2 109.3(2) . . ?
O4 S2 N2 109.23(19) . . ?
O3 S2 C5 104.8(2) . . ?
O4 S2 C5 104.6(2) . . ?
N2 S2 C5 104.9(2) . . ?
O7 S3 O8 123.2(3) . . ?
O7 S3 N3 108.9(2) . . ?
O8 S3 N3 109.6(2) . . ?
O7 S3 C9 104.1(3) . . ?
O8 S3 C9 104.1(2) . . ?
N3 S3 C9 105.3(2) . . ?
O5 S4 O6 122.5(2) . . ?
O5 S4 N4 109.5(2) . . ?
O6 S4 N4 109.1(2) . . ?
O5 S4 C13 104.2(2) . . ?
O6 S4 C13 103.8(2) . . ?
N4 S4 C13 106.3(2) . . ?
N2 C2 C4 113.8(3) . . ?
N2 C2 H2 108.8 . . ?
C4 C2 H2 108.8 . . ?
N2 C2 H1 108.8 . . ?
C4 C2 H1 108.8 . . ?
H2 C2 H1 107.7 . . ?
C2 N2 C8 120.6(3) . . ?
C2 N2 S2 119.6(3) . . ?
C8 N2 S2 118.9(3) . . ?
C10 N3 C14 120.6(3) . . ?
C10 N3 S3 119.1(3) . . ?
C14 N3 S3 119.1(3) . . ?
C12 N4 C16 120.4(3) . . ?
C12 N4 S4 118.4(3) . . ?
C16 N4 S4 119.9(3) . . ?
F4 C1 F5 108.5(5) . . ?
F4 C1 F1 108.8(4) . . ?
F5 C1 F1 108.7(4) . . ?
F4 C1 S1 111.0(3) . . ?
F5 C1 S1 110.7(3) . . ?
F1 C1 S1 109.1(4) . . ?
C6 N1 C3 120.0(4) . . ?
C6 N1 S1 120.0(3) . . ?
C3 N1 S1 119.0(3) . . ?
N1 C3 C4 113.8(3) . . ?
N1 C3 H4 108.8 . . ?
C4 C3 H4 108.8 . . ?
N1 C3 H3 108.8 . . ?
C4 C3 H3 108.8 . . ?
H4 C3 H3 107.7 . . ?
C2 C4 C3 117.2(4) . . ?
C2 C4 I1 106.3(3) . . ?
C3 C4 I1 106.7(3) . . ?
C2 C4 H10 108.8 . . ?
C3 C4 H10 108.8 . . ?
I1 C4 H10 108.8 . . ?
F2 C5 F3 108.7(5) . . ?
F2 C5 F6 108.8(4) . . ?
F3 C5 F6 108.5(5) . . ?
F2 C5 S2 110.6(4) . . ?
F3 C5 S2 110.4(4) . . ?
F6 C5 S2 109.9(4) . . ?
N1 C6 C7 113.5(3) . . ?
N1 C6 H5 108.9 . . ?
C7 C6 H5 108.9 . . ?
N1 C6 H6 108.9 . . ?
C7 C6 H6 108.9 . . ?
H5 C6 H6 107.7 . . ?
C8 C7 C6 116.8(4) . . ?
C8 C7 I2 107.1(3) . . ?
C6 C7 I2 105.6(3) . . ?
C8 C7 H7 109.0 . . ?
C6 C7 H7 109.0 . . ?
I2 C7 H7 109.0 . . ?
N2 C8 C7 113.1(3) . . ?
N2 C8 H9 109.0 . . ?
C7 C8 H9 109.0 . . ?
N2 C8 H8 109.0 . . ?
C7 C8 H8 109.0 . . ?
H9 C8 H8 107.8 . . ?
F11 C9 F10 107.7(5) . . ?
F11 C9 F7 110.7(6) . . ?
F10 C9 F7 103.7(6) . . ?
F11 C9 S3 110.9(4) . . ?
F10 C9 S3 112.1(4) . . ?
F7 C9 S3 111.6(4) . . ?
N3 C10 C11 112.6(3) . . ?
N3 C10 H17 109.1 . . ?
C11 C10 H17 109.1 . . ?
N3 C10 H16 109.1 . . ?
C11 C10 H16 109.1 . . ?
H17 C10 H16 107.8 . . ?
C12 C11 C10 116.2(4) . . ?
C12 C11 I3 105.7(3) . . ?
C10 C11 I3 106.8(3) . . ?
C12 C11 H18 109.3 . . ?
C10 C11 H18 109.3 . . ?
I3 C11 H18 109.3 . . ?
N4 C12 C11 113.5(3) . . ?
N4 C12 H20 108.9 . . ?
C11 C12 H20 108.9 . . ?
N4 C12 H19 108.9 . . ?
C11 C12 H19 108.9 . . ?
H20 C12 H19 107.7 . . ?
F8 C13 F9 108.4(4) . . ?
F8 C13 F12 109.4(5) . . ?
F9 C13 F12 107.4(5) . . ?
F8 C13 S4 109.4(4) . . ?
F9 C13 S4 111.3(3) . . ?
F12 C13 S4 111.0(3) . . ?
N3 C14 C15 113.1(3) . . ?
N3 C14 H11 109.0 . . ?
C15 C14 H11 109.0 . . ?
N3 C14 H15 109.0 . . ?
C15 C14 H15 109.0 . . ?
H11 C14 H15 107.8 . . ?
C14 C15 C16 117.5(4) . . ?
C14 C15 I4 107.0(3) . . ?
C16 C15 I4 106.2(3) . . ?
C14 C15 H14 108.6 . . ?
C16 C15 H14 108.6 . . ?
I4 C15 H14 108.6 . . ?
N4 C16 C15 112.8(3) . . ?
N4 C16 H12 109.0 . . ?
C15 C16 H12 109.0 . . ?
N4 C16 H13 109.0 . . ?
C15 C16 H13 109.0 . . ?
H12 C16 H13 107.8 . . ?

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
C4 C2 N2 C8 104.7(4) . . . . ?
C4 C2 N2 S2 -86.1(4) . . . . ?
O3 S2 N2 C2 30.4(4) . . . . ?
O4 S2 N2 C2 166.9(3) . . . . ?
C5 S2 N2 C2 -81.5(4) . . . . ?
O3 S2 N2 C8 -160.2(3) . . . . ?
O4 S2 N2 C8 -23.7(4) . . . . ?
C5 S2 N2 C8 87.9(3) . . . . ?
O7 S3 N3 C10 -25.7(4) . . . . ?
O8 S3 N3 C10 -163.1(3) . . . . ?
C9 S3 N3 C10 85.5(4) . . . . ?
O7 S3 N3 C14 167.0(3) . . . . ?
O8 S3 N3 C14 29.5(4) . . . . ?
C9 S3 N3 C14 -81.9(4) . . . . ?
O5 S4 N4 C12 27.5(4) . . . . ?
O6 S4 N4 C12 164.1(3) . . . . ?
C13 S4 N4 C12 -84.6(3) . . . . ?
O5 S4 N4 C16 -165.8(3) . . . . ?
O6 S4 N4 C16 -29.1(4) . . . . ?
C13 S4 N4 C16 82.2(4) . . . . ?
O2 S1 C1 F4 172.6(3) . . . . ?
O1 S1 C1 F4 -58.2(4) . . . . ?
N1 S1 C1 F4 56.5(4) . . . . ?
O2 S1 C1 F5 52.0(4) . . . . ?
O1 S1 C1 F5 -178.7(4) . . . . ?
N1 S1 C1 F5 -64.0(4) . . . . ?
O2 S1 C1 F1 -67.5(4) . . . . ?
O1 S1 C1 F1 61.8(4) . . . . ?
N1 S1 C1 F1 176.5(3) . . . . ?
O2 S1 N1 C6 162.7(3) . . . . ?
O1 S1 N1 C6 26.5(4) . . . . ?
C1 S1 N1 C6 -84.5(3) . . . . ?
O2 S1 N1 C3 -28.5(4) . . . . ?
O1 S1 N1 C3 -164.7(3) . . . . ?
C1 S1 N1 C3 84.3(3) . . . . ?
C6 N1 C3 C4 -105.0(4) . . . . ?
S1 N1 C3 C4 86.2(4) . . . . ?
N2 C2 C4 C3 -62.5(5) . . . . ?
N2 C2 C4 I1 178.4(3) . . . . ?
N1 C3 C4 C2 63.2(5) . . . . ?
N1 C3 C4 I1 -177.9(3) . . . . ?
O3 S2 C5 F2 -52.9(4) . . . . ?
O4 S2 C5 F2 177.0(4) . . . . ?
N2 S2 C5 F2 62.1(4) . . . . ?
O3 S2 C5 F3 -173.3(4) . . . . ?
O4 S2 C5 F3 56.7(4) . . . . ?
N2 S2 C5 F3 -58.2(4) . . . . ?
O3 S2 C5 F6 67.2(4) . . . . ?
O4 S2 C5 F6 -62.9(5) . . . . ?
N2 S2 C5 F6 -177.8(4) . . . . ?
C3 N1 C6 C7 105.1(4) . . . . ?
S1 N1 C6 C7 -86.2(4) . . . . ?
N1 C6 C7 C8 -64.4(5) . . . . ?
N1 C6 C7 I2 176.7(3) . . . . ?
C2 N2 C8 C7 -105.8(4) . . . . ?
S2 N2 C8 C7 84.9(4) . . . . ?
C6 C7 C8 N2 64.3(5) . . . . ?
I2 C7 C8 N2 -177.6(3) . . . . ?
O7 S3 C9 F11 -44.3(5) . . . . ?
O8 S3 C9 F11 85.9(5) . . . . ?
N3 S3 C9 F11 -158.8(5) . . . . ?
O7 S3 C9 F10 -164.7(4) . . . . ?
O8 S3 C9 F10 -34.5(5) . . . . ?
N3 S3 C9 F10 80.8(5) . . . . ?
O7 S3 C9 F7 79.6(5) . . . . ?
O8 S3 C9 F7 -150.2(5) . . . . ?
N3 S3 C9 F7 -35.0(5) . . . . ?
C14 N3 C10 C11 -104.3(4) . . . . ?
S3 N3 C10 C11 88.6(4) . . . . ?
N3 C10 C11 C12 64.2(5) . . . . ?
N3 C10 C11 I3 -178.1(3) . . . . ?
C16 N4 C12 C11 107.4(4) . . . . ?
S4 N4 C12 C11 -85.8(4) . . . . ?
C10 C11 C12 N4 -66.9(5) . . . . ?
I3 C11 C12 N4 174.8(3) . . . . ?
O5 S4 C13 F8 69.8(4) . . . . ?
O6 S4 C13 F8 -59.5(4) . . . . ?
N4 S4 C13 F8 -174.5(4) . . . . ?
O5 S4 C13 F9 -170.5(4) . . . . ?
O6 S4 C13 F9 60.2(4) . . . . ?
N4 S4 C13 F9 -54.9(4) . . . . ?
O5 S4 C13 F12 -51.0(4) . . . . ?
O6 S4 C13 F12 179.7(4) . . . . ?
N4 S4 C13 F12 64.7(4) . . . . ?
C10 N3 C14 C15 106.5(4) . . . . ?
S3 N3 C14 C15 -86.3(4) . . . . ?
N3 C14 C15 C16 -65.5(5) . . . . ?
N3 C14 C15 I4 175.3(3) . . . . ?
C12 N4 C16 C15 -103.3(4) . . . . ?
S4 N4 C16 C15 90.2(4) . . . . ?
C14 C15 C16 N4 63.4(5) . . . . ?
I4 C15 C16 N4 -177.0(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
C16 H12 F9 0.99 2.60 3.235(5) 122.2 .
C15 H14 O8 1.00 2.55 3.173(6) 120.3 .
C15 H14 O6 1.00 2.66 3.247(6) 117.8 .
C14 H15 I2 0.99 3.26 4.166(4) 152.4 4_566
C12 H20 O4 0.99 2.57 3.053(5) 110.3 3_766
C12 H20 O1 0.99 2.59 3.481(5) 149.5 3_766
C11 H18 O7 1.00 2.62 3.200(6) 116.8 .
C11 H18 O5 1.00 2.54 3.144(6) 119.0 .
C10 H16 O1 0.99 2.60 3.474(6) 147.2 3_766
C10 H17 F7 0.99 2.64 3.165(6) 113.3 .
C7 H7 O4 1.00 2.55 3.157(5) 118.8 .
C7 H7 O1 1.00 2.59 3.193(5) 118.5 .
C6 H6 F4 0.99 2.62 3.264(5) 122.7 .
C6 H5 O8 0.99 2.64 3.190(6) 115.3 3_666
C4 H10 O3 1.00 2.57 3.181(6) 119.5 .
C4 H10 O2 1.00 2.58 3.187(5) 119.0 .
C3 H3 O6 0.99 2.60 3.463(6) 145.2 3_666
C3 H4 F5 0.99 2.63 3.304(6) 125.3 .
C2 H1 O7 0.99 2.65 3.341(5) 126.9 2_655
C2 H1 F2 0.99 2.54 3.226(5) 126.5 .
C2 H2 O6 0.99 2.53 3.407(6) 147.4 3_666
C16 H12 F9 0.99 2.60 3.235(5) 122.2 .
C15 H14 O8 1.00 2.55 3.173(6) 120.3 .
C14 H15 I2 0.99 3.26 4.166(4) 152.4 4_566
C12 H19 F12 0.99 2.64 3.320(5) 125.9 .
C12 H20 O4 0.99 2.57 3.053(5) 110.3 3_766
C12 H20 O1 0.99 2.59 3.481(5) 149.5 3_766
C11 H18 O7 1.00 2.62 3.200(6) 116.8 .
C11 H18 O5 1.00 2.54 3.144(6) 119.0 .
C10 H16 O1 0.99 2.60 3.474(6) 147.2 3_766
C10 H17 F7 0.99 2.64 3.165(6) 113.3 .
C7 H7 O4 1.00 2.55 3.157(5) 118.8 .
C7 H7 O1 1.00 2.59 3.193(5) 118.5 .
C6 H6 F4 0.99 2.62 3.264(5) 122.7 .
C6 H5 O8 0.99 2.64 3.190(6) 115.3 3_666
C4 H10 O3 1.00 2.57 3.181(6) 119.5 .
C4 H10 O2 1.00 2.58 3.187(5) 119.0 .
C3 H3 O6 0.99 2.60 3.463(6) 145.2 3_666
C3 H4 F5 0.99 2.63 3.304(6) 125.3 .
C2 H1 O7 0.99 2.65 3.341(5) 126.9 2_655
C2 H1 F2 0.99 2.54 3.226(5) 126.5 .
C2 H2 O6 0.99 2.53 3.407(6) 147.4 3_666
C16 H12 F9 0.99 2.60 3.235(5) 122.2 .
C15 H14 O8 1.00 2.55 3.173(6) 120.3 .
C15 H14 O6 1.00 2.66 3.247(6) 117.8 .
C11 H18 O7 1.00 2.62 3.200(6) 116.8 .
C11 H18 O5 1.00 2.54 3.144(6) 119.0 .
C7 H7 O4 1.00 2.55 3.157(5) 118.8 .
C7 H7 O1 1.00 2.59 3.193(5) 118.5 .
C6 H6 F4 0.99 2.62 3.264(5) 122.7 .
C4 H10 O3 1.00 2.57 3.181(6) 119.5 .
C4 H10 O2 1.00 2.58 3.187(5) 119.0 .
C3 H4 F5 0.99 2.63 3.304(6) 125.3 .
C2 H2 O6 0.99 2.53 3.407(6) 147.4 3_666
C2 H1 F2 0.99 2.54 3.226(5) 126.5 .
C2 H1 O7 0.99 2.65 3.341(5) 126.9 2_655
C3 H4 F5 0.99 2.63 3.304(6) 125.3 .
C3 H3 O6 0.99 2.60 3.463(6) 145.2 3_666
C4 H10 O2 1.00 2.58 3.187(5) 119.0 .
C4 H10 O3 1.00 2.57 3.181(6) 119.5 .
C6 H5 O8 0.99 2.64 3.190(6) 115.3 3_666
C6 H6 F4 0.99 2.62 3.264(5) 122.7 .
C7 H7 O1 1.00 2.59 3.193(5) 118.5 .
C7 H7 O4 1.00 2.55 3.157(5) 118.8 .
C10 H17 F7 0.99 2.64 3.165(6) 113.3 .
C10 H16 O1 0.99 2.60 3.474(6) 147.2 3_766
C11 H18 O5 1.00 2.54 3.144(6) 119.0 .
C11 H18 O7 1.00 2.62 3.200(6) 116.8 .
C12 H20 O1 0.99 2.59 3.481(5) 149.5 3_766
C12 H20 O4 0.99 2.57 3.053(5) 110.3 3_766
C14 H15 I2 0.99 3.26 4.166(4) 152.4 4_566
C15 H14 O6 1.00 2.66 3.247(6) 117.8 .
C15 H14 O8 1.00 2.55 3.173(6) 120.3 .
C16 H12 F9 0.99 2.60 3.235(5) 122.2 .

_refine_diff_density_max         2.096
_refine_diff_density_min         -2.015
_refine_diff_density_rms         0.159

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
