# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# 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_4h
_database_code_depnum_ccdc_archive 'CCDC 2430944'
loop_
_audit_author_name
_audit_author_address
'Borodina Tatiana'
;Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Science
Russia
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2025-02-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
N-(6-iodo-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-yl)-N'-((4-(trifluoromethyl)phenyl)sulfonyl)acetimidamide
_chemical_formula_moiety         'C24 H32 F3 I N2 O2 S'
_chemical_formula_sum            'C24 H32 F3 I N2 O2 S'
_chemical_formula_weight         596.47
_chemical_absolute_configuration .
_chemical_melting_point          466.6
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.5276(11)
_cell_length_b                   11.5823(12)
_cell_length_c                   10.7820(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.162(3)
_cell_angle_gamma                90
_cell_volume                     1309.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.725
_shelx_estimated_absorpt_T_min   0.499
_exptl_absorpt_coefficient_mu    1.347
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1715 before and 0.0811 after correction.
The Ratio of minimum to maximum transmission is 0.5915.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.255
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27070
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         1.896
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                4641
_reflns_number_total             5668
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (BRUKER, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.32B (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 
;
 Flack x determined using 1839 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.011(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5668
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0735P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1204
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(F2) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of
0.05 and sigma for terminal atoms of 0.1
3.a Ternary CH refined with riding coordinates:
 C6(H6), C3(H3), C9A(H9A)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C4(H4A,H4B), C9(H9B,H9C), C8(H8A,H8B), C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C17(H17), C18(H18), C20(H20), C21(H21)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C12(H12A,H12B,
 H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.48839(4) 0.42119(8) 0.76371(5) 0.0996(3) Uani 1 1 d . . . . .
S1 S 0.10826(12) 0.53642(9) 0.34186(9) 0.0384(3) Uani 1 1 d . . . . .
O1 O 0.0751(4) 0.4532(3) 0.2456(3) 0.0517(9) Uani 1 1 d . . . . .
N1 N 0.0021(4) 0.3861(3) 0.6257(3) 0.0333(7) Uani 1 1 d . . . . .
H1 H -0.0131 0.3163 0.6474 0.040 Uiso 1 1 calc R U . . .
N2 N 0.0635(4) 0.5070(3) 0.4761(3) 0.0362(8) Uani 1 1 d . . . . .
O2 O 0.0717(4) 0.6540(3) 0.3152(3) 0.0574(10) Uani 1 1 d . . . . .
C3A C 0.1046(5) 0.4905(4) 0.8162(3) 0.0332(8) Uani 1 1 d . . . . .
C2 C -0.1228(4) 0.4511(4) 0.7951(4) 0.0367(9) Uani 1 1 d . . . . .
H2A H -0.2035 0.4637 0.7460 0.044 Uiso 1 1 calc R U . . .
H2B H -0.1199 0.3723 0.8257 0.044 Uiso 1 1 calc R U . . .
C6 C 0.3754(5) 0.4835(6) 0.9131(5) 0.0601(14) Uani 1 1 d . . . . .
H6 H 0.4342 0.4962 0.9876 0.072 Uiso 1 1 calc R U . . .
C5 C 0.2850(5) 0.3855(5) 0.9418(5) 0.0521(13) Uani 1 1 d . . . . .
H5A H 0.3319 0.3133 0.9473 0.063 Uiso 1 1 calc R U . . .
H5B H 0.2527 0.3996 1.0219 0.063 Uiso 1 1 calc R U . . .
C4 C 0.1732(5) 0.3746(4) 0.8425(4) 0.0390(10) Uani 1 1 d . . . . .
H4A H 0.1129 0.3187 0.8696 0.047 Uiso 1 1 calc R U . . .
H4B H 0.2040 0.3461 0.7661 0.047 Uiso 1 1 calc R U . . .
C3 C -0.0106(4) 0.4761(3) 0.7188(3) 0.0306(8) Uani 1 1 d . . . . .
H3 H -0.0262 0.5499 0.6756 0.037 Uiso 1 1 calc R U . . .
C14 C 0.0350(4) 0.4018(4) 0.5114(3) 0.0320(8) Uani 1 1 d . . . . .
C16 C 0.2776(5) 0.5362(4) 0.3666(4) 0.0431(10) Uani 1 1 d . . . . .
C17 C 0.3453(6) 0.4453(5) 0.3271(6) 0.0633(14) Uani 1 1 d . . . . .
H17 H 0.3025 0.3822 0.2899 0.076 Uiso 1 1 calc R U . . .
C18 C 0.4766(7) 0.4458(8) 0.3416(8) 0.085(2) Uani 1 1 d . . . . .
H18 H 0.5223 0.3843 0.3125 0.102 Uiso 1 1 calc R U . . .
C19 C 0.5388(7) 0.5365(8) 0.3986(6) 0.0774(18) Uani 1 1 d . . . . .
C22 C 0.6790(9) 0.5334(15) 0.4096(10) 0.120(4) Uani 1 1 d . . . . .
C15 C 0.0351(7) 0.2931(4) 0.4347(5) 0.0560(14) Uani 1 1 d . . . . .
H15A H 0.0209 0.2277 0.4863 0.084 Uiso 1 1 calc R U . . .
H15B H 0.1160 0.2851 0.4010 0.084 Uiso 1 1 calc R U . . .
H15C H -0.0315 0.2973 0.3679 0.084 Uiso 1 1 calc R U . . .
C20 C 0.4720(8) 0.6287(7) 0.4394(8) 0.087(2) Uani 1 1 d . . . . .
H20 H 0.5153 0.6910 0.4776 0.104 Uiso 1 1 calc R U . . .
C21 C 0.3404(7) 0.6288(6) 0.4236(7) 0.0720(17) Uani 1 1 d . . . . .
H21 H 0.2946 0.6910 0.4513 0.086 Uiso 1 1 calc R U . . .
C1 C -0.1047(5) 0.5371(4) 0.9022(4) 0.0391(9) Uani 1 1 d . . . . .
C11 C -0.1764(6) 0.5007(5) 1.0133(4) 0.0540(13) Uani 1 1 d . . . . .
H11A H -0.2665 0.5016 0.9896 0.081 Uiso 1 1 calc R U . . .
H11B H -0.1571 0.5536 1.0810 0.081 Uiso 1 1 calc R U . . .
H11C H -0.1506 0.4243 1.0391 0.081 Uiso 1 1 calc R U . . .
C9A C 0.0420(4) 0.5345(4) 0.9347(3) 0.0365(9) Uani 1 1 d . . . . .
H9A H 0.0589 0.4754 0.9991 0.044 Uiso 1 1 calc R U . . .
C9 C 0.1032(6) 0.6462(5) 0.9865(5) 0.0550(14) Uani 1 1 d . . . . .
H9B H 0.0793 0.7093 0.9301 0.066 Uiso 1 1 calc R U . . .
H9C H 0.0716 0.6635 1.0662 0.066 Uiso 1 1 calc R U . . .
C8 C 0.2463(7) 0.6362(6) 1.0028(5) 0.0650(17) Uani 1 1 d . . . . .
H8A H 0.2698 0.5805 1.0681 0.078 Uiso 1 1 calc R U . . .
H8B H 0.2820 0.7102 1.0298 0.078 Uiso 1 1 calc R U . . .
C7 C 0.3069(6) 0.5981(5) 0.8810(5) 0.0553(14) Uani 1 1 d . . . . .
C13 C 0.3973(8) 0.6944(7) 0.8450(7) 0.084(2) Uani 1 1 d . . . . .
H13A H 0.4687 0.6996 0.9068 0.127 Uiso 1 1 calc R U . . .
H13B H 0.3525 0.7667 0.8402 0.127 Uiso 1 1 calc R U . . .
H13C H 0.4273 0.6771 0.7656 0.127 Uiso 1 1 calc R U . . .
C10 C 0.2016(5) 0.5781(4) 0.7772(4) 0.0427(11) Uani 1 1 d . . . . .
H10A H 0.2387 0.5502 0.7037 0.051 Uiso 1 1 calc R U . . .
H10B H 0.1589 0.6506 0.7562 0.051 Uiso 1 1 calc R U . . .
C12 C -0.1556(7) 0.6562(5) 0.8574(5) 0.0568(14) Uani 1 1 d . . . . .
H12A H -0.1139 0.6797 0.7859 0.085 Uiso 1 1 calc R U . . .
H12B H -0.1386 0.7118 0.9229 0.085 Uiso 1 1 calc R U . . .
H12C H -0.2459 0.6514 0.8356 0.085 Uiso 1 1 calc R U . . .
F1 F 0.7293(9) 0.5875(12) 0.5146(10) 0.198(4) Uani 1 1 d . U . . .
F2 F 0.7324(8) 0.5860(14) 0.3308(10) 0.226(5) Uani 1 1 d . U . . .
F3 F 0.7286(8) 0.4435(13) 0.4378(14) 0.248(5) Uani 1 1 d . 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 C6 2.208(6) . ?
S1 O1 1.436(3) . ?
S1 N2 1.599(4) . ?
S1 O2 1.437(3) . ?
S1 C16 1.779(5) . ?
N1 H1 0.8600 . ?
N1 C3 1.462(5) . ?
N1 C14 1.322(5) . ?
N2 C14 1.319(6) . ?
C3A C4 1.539(6) . ?
C3A C3 1.540(6) . ?
C3A C9A 1.574(6) . ?
C3A C10 1.525(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.526(6) . ?
C2 C1 1.524(6) . ?
C6 H6 0.9800 . ?
C6 C5 1.531(8) . ?
C6 C7 1.535(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.523(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3 0.9800 . ?
C14 C15 1.507(6) . ?
C16 C17 1.360(8) . ?
C16 C21 1.377(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.355(12) . ?
C19 C22 1.470(12) . ?
C19 C20 1.373(12) . ?
C22 F1 1.360(16) . ?
C22 F2 1.223(14) . ?
C22 F3 1.192(16) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C21 1.380(12) . ?
C21 H21 0.9300 . ?
C1 C11 1.532(6) . ?
C1 C9A 1.552(7) . ?
C1 C12 1.542(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C9A H9A 0.9800 . ?
C9A C9 1.529(6) . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C9 C8 1.505(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.574(9) . ?
C7 C13 1.540(8) . ?
C7 C10 1.520(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 N2 116.0(2) . . ?
O1 S1 O2 116.6(2) . . ?
O1 S1 C16 106.4(2) . . ?
N2 S1 C16 103.7(2) . . ?
O2 S1 N2 106.72(19) . . ?
O2 S1 C16 106.2(3) . . ?
C3 N1 H1 117.0 . . ?
C14 N1 H1 117.0 . . ?
C14 N1 C3 126.1(3) . . ?
C14 N2 S1 123.5(3) . . ?
C4 C3A C3 111.0(3) . . ?
C4 C3A C9A 110.9(3) . . ?
C3 C3A C9A 103.1(3) . . ?
C10 C3A C4 108.4(4) . . ?
C10 C3A C3 113.0(3) . . ?
C10 C3A C9A 110.4(3) . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C1 C2 C3 103.5(3) . . ?
I1 C6 H6 107.7 . . ?
C5 C6 I1 106.9(4) . . ?
C5 C6 H6 107.7 . . ?
C5 C6 C7 113.5(5) . . ?
C7 C6 I1 113.0(4) . . ?
C7 C6 H6 107.7 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C4 C5 C6 112.0(4) . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C3A C4 H4A 109.2 . . ?
C3A C4 H4B 109.2 . . ?
C5 C4 C3A 112.2(4) . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N1 C3 C3A 115.4(3) . . ?
N1 C3 C2 111.0(3) . . ?
N1 C3 H3 108.5 . . ?
C3A C3 H3 108.5 . . ?
C2 C3 C3A 104.7(3) . . ?
C2 C3 H3 108.5 . . ?
N1 C14 C15 114.2(4) . . ?
N2 C14 N1 118.8(3) . . ?
N2 C14 C15 127.0(4) . . ?
C17 C16 S1 120.0(4) . . ?
C17 C16 C21 120.0(6) . . ?
C21 C16 S1 120.0(4) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(6) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(7) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C22 117.2(9) . . ?
C18 C19 C20 120.5(7) . . ?
C20 C19 C22 122.2(10) . . ?
F1 C22 C19 111.7(10) . . ?
F2 C22 C19 116.9(9) . . ?
F2 C22 F1 100.4(14) . . ?
F3 C22 C19 117.1(12) . . ?
F3 C22 F1 93.5(10) . . ?
F3 C22 F2 113.2(13) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.9(7) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 119.4(7) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C2 C1 C11 112.1(4) . . ?
C2 C1 C9A 102.3(3) . . ?
C2 C1 C12 109.3(4) . . ?
C11 C1 C9A 111.6(4) . . ?
C11 C1 C12 108.0(4) . . ?
C12 C1 C9A 113.5(4) . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3A C9A H9A 106.7 . . ?
C1 C9A C3A 107.7(3) . . ?
C1 C9A H9A 106.7 . . ?
C9 C9A C3A 112.2(4) . . ?
C9 C9A C1 116.4(4) . . ?
C9 C9A H9A 106.7 . . ?
C9A C9 H9B 109.4 . . ?
C9A C9 H9C 109.4 . . ?
H9B C9 H9C 108.0 . . ?
C8 C9 C9A 111.2(5) . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 H9C 109.4 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C9 C8 C7 113.6(4) . . ?
H8A C8 H8B 107.7 . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C6 C7 C8 105.8(5) . . ?
C6 C7 C13 113.2(6) . . ?
C13 C7 C8 108.3(5) . . ?
C10 C7 C6 109.4(4) . . ?
C10 C7 C8 109.5(5) . . ?
C10 C7 C13 110.5(5) . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3A C10 H10A 109.4 . . ?
C3A C10 H10B 109.4 . . ?
C7 C10 C3A 111.1(4) . . ?
C7 C10 H10A 109.4 . . ?
C7 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C6 C5 C4 -75.9(5) . . . . ?
I1 C6 C7 C8 -173.2(3) . . . . ?
I1 C6 C7 C13 -54.8(5) . . . . ?
I1 C6 C7 C10 69.0(5) . . . . ?
S1 N2 C14 N1 178.3(3) . . . . ?
S1 N2 C14 C15 -1.8(7) . . . . ?
S1 C16 C17 C18 177.7(5) . . . . ?
S1 C16 C21 C20 -178.4(6) . . . . ?
O1 S1 N2 C14 20.9(5) . . . . ?
O1 S1 C16 C17 -18.8(5) . . . . ?
O1 S1 C16 C21 160.1(4) . . . . ?
N2 S1 C16 C17 104.1(4) . . . . ?
N2 S1 C16 C21 -77.1(5) . . . . ?
O2 S1 N2 C14 152.8(4) . . . . ?
O2 S1 C16 C17 -143.6(4) . . . . ?
O2 S1 C16 C21 35.2(5) . . . . ?
C3A C9A C9 C8 -50.1(5) . . . . ?
C2 C1 C9A C3A 22.8(4) . . . . ?
C2 C1 C9A C9 149.7(4) . . . . ?
C6 C5 C4 C3A -51.4(6) . . . . ?
C6 C7 C10 C3A 59.8(6) . . . . ?
C5 C6 C7 C8 64.9(6) . . . . ?
C5 C6 C7 C13 -176.7(5) . . . . ?
C5 C6 C7 C10 -53.0(6) . . . . ?
C4 C3A C3 N1 -31.2(5) . . . . ?
C4 C3A C3 C2 91.1(4) . . . . ?
C4 C3A C9A C1 -116.1(4) . . . . ?
C4 C3A C9A C9 114.7(4) . . . . ?
C4 C3A C10 C7 -62.0(5) . . . . ?
C3 N1 C14 N2 2.3(6) . . . . ?
C3 N1 C14 C15 -177.6(4) . . . . ?
C3 C3A C4 C5 -178.1(4) . . . . ?
C3 C3A C9A C1 2.8(4) . . . . ?
C3 C3A C9A C9 -126.4(4) . . . . ?
C3 C3A C10 C7 174.5(4) . . . . ?
C3 C2 C1 C11 -159.8(4) . . . . ?
C3 C2 C1 C9A -40.1(4) . . . . ?
C3 C2 C1 C12 80.5(5) . . . . ?
C14 N1 C3 C3A -98.8(5) . . . . ?
C14 N1 C3 C2 142.4(4) . . . . ?
C16 S1 N2 C14 -95.4(4) . . . . ?
C16 C17 C18 C19 1.6(11) . . . . ?
C17 C16 C21 C20 0.4(10) . . . . ?
C17 C18 C19 C22 -178.9(7) . . . . ?
C17 C18 C19 C20 -1.4(12) . . . . ?
C18 C19 C22 F1 -148.2(11) . . . . ?
C18 C19 C22 F2 97.0(16) . . . . ?
C18 C19 C22 F3 -42.1(16) . . . . ?
C18 C19 C20 C21 0.7(12) . . . . ?
C19 C20 C21 C16 -0.2(12) . . . . ?
C22 C19 C20 C21 178.1(8) . . . . ?
C20 C19 C22 F1 34.3(14) . . . . ?
C20 C19 C22 F2 -80.5(17) . . . . ?
C20 C19 C22 F3 140.4(14) . . . . ?
C21 C16 C17 C18 -1.1(9) . . . . ?
C1 C2 C3 N1 168.5(3) . . . . ?
C1 C2 C3 C3A 43.3(4) . . . . ?
C1 C9A C9 C8 -174.7(4) . . . . ?
C11 C1 C9A C3A 142.9(4) . . . . ?
C11 C1 C9A C9 -90.3(5) . . . . ?
C9A C3A C4 C5 -64.1(5) . . . . ?
C9A C3A C3 N1 -150.0(3) . . . . ?
C9A C3A C3 C2 -27.7(4) . . . . ?
C9A C3A C10 C7 59.6(5) . . . . ?
C9A C9 C8 C7 54.3(6) . . . . ?
C9 C8 C7 C6 -119.1(5) . . . . ?
C9 C8 C7 C13 119.2(6) . . . . ?
C9 C8 C7 C10 -1.4(7) . . . . ?
C8 C7 C10 C3A -55.7(6) . . . . ?
C7 C6 C5 C4 49.4(7) . . . . ?
C13 C7 C10 C3A -174.9(6) . . . . ?
C10 C3A C4 C5 57.3(5) . . . . ?
C10 C3A C3 N1 90.9(4) . . . . ?
C10 C3A C3 C2 -146.8(4) . . . . ?
C10 C3A C9A C1 123.8(4) . . . . ?
C10 C3A C9A C9 -5.5(5) . . . . ?
C12 C1 C9A C3A -94.8(4) . . . . ?
C12 C1 C9A C9 32.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichlormetan-methanol'
####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 2430946'
loop_
_audit_author_name
_audit_author_address
'Borodina Tatiana'
;Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Science
Russia
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2025-02-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
N-(9-iodo-4,4,8-trimethyltricyclo[6.3.1.0^2,5]dodecan-1-yl)-N'-((trifluoromethyl)sulfonyl)acetimidamide
_chemical_formula_moiety         'C18 H28 F3 I N2 O2 S'
_chemical_formula_sum            'C18 H28 F3 I N2 O2 S'
_chemical_formula_weight         520.38
_chemical_absolute_configuration .
_chemical_melting_point          462.6
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.2852(9)
_cell_length_b                   16.239(2)
_cell_length_c                   18.497(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2188.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.659
_shelx_estimated_absorpt_T_min   0.447
_exptl_absorpt_coefficient_mu    1.599
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1721 before and 0.0821 after correction.
The Ratio of minimum to maximum transmission is 0.5258.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.445
_exptl_crystal_size_min          0.285
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1107
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41380
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.747
_diffrn_reflns_theta_min         2.202
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3483
_reflns_number_total             5080
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (BRUKER, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.32B (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details 
;
 Flack x determined using 1209 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0801
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C10(H10A,H10B), C11(H11A,H11B), C7(H7A,H7B), C6(H6A,H6B),
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,
 H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.3, Nqual =  -0, Ralpha = 0.020
;
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 0.46379(6) -0.16621(2) 0.32057(2) 0.08642(19) Uani 1 1 d . . . . .
S1 S -0.25096(14) 0.17342(5) 0.38595(5) 0.0338(2) Uani 1 1 d . . . . .
F1 F -0.3320(6) 0.01995(16) 0.41121(18) 0.0884(12) Uani 1 1 d . . . . .
F2 F -0.1589(8) 0.0743(3) 0.4888(2) 0.1259(17) Uani 1 1 d . . . . .
F3 F -0.4395(7) 0.1047(2) 0.4874(2) 0.1185(17) Uani 1 1 d . . . . .
O1 O -0.4070(4) 0.17614(18) 0.33970(17) 0.0540(8) Uani 1 1 d . . . . .
O2 O -0.2226(5) 0.24246(16) 0.43207(18) 0.0577(9) Uani 1 1 d . . . . .
N2 N -0.0840(5) 0.13936(17) 0.34259(17) 0.0328(7) Uani 1 1 d . . . . .
N1 N 0.2142(4) 0.12503(17) 0.31068(17) 0.0323(7) Uani 1 1 d . . . . .
H1 H 0.3273 0.1434 0.3152 0.039 Uiso 1 1 calc R U . . .
C18 C -0.2979(9) 0.0882(3) 0.4468(3) 0.0626(15) Uani 1 1 d . . . . .
C16 C 0.0891(5) 0.1626(2) 0.34937(19) 0.0299(8) Uani 1 1 d . . . . .
C1 C 0.1876(6) 0.05467(19) 0.2598(2) 0.0305(8) Uani 1 1 d . . . . .
C2 C 0.0826(6) 0.08160(19) 0.1919(2) 0.0319(8) Uani 1 1 d . . . . .
H2 H 0.0078 0.0334 0.1756 0.038 Uiso 1 1 calc R U . . .
C5 C 0.1956(7) 0.1108(2) 0.1264(2) 0.0434(10) Uani 1 1 d . . . . .
H5 H 0.2896 0.1506 0.1446 0.052 Uiso 1 1 calc R U . . .
C4 C 0.0263(7) 0.1614(2) 0.1021(2) 0.0468(10) Uani 1 1 d . . . . .
C14 C -0.1041(9) 0.1150(3) 0.0526(3) 0.0617(15) Uani 1 1 d . . . . .
H14A H -0.2271 0.1391 0.0561 0.092 Uiso 1 1 calc R U . . .
H14B H -0.1088 0.0570 0.0671 0.092 Uiso 1 1 calc R U . . .
H14C H -0.0604 0.1190 0.0026 0.092 Uiso 1 1 calc R U . . .
C12 C 0.3837(6) 0.0291(2) 0.2384(2) 0.0382(10) Uani 1 1 d . . . . .
H12A H 0.4425 0.0757 0.2129 0.046 Uiso 1 1 calc R U . . .
H12B H 0.4550 0.0186 0.2830 0.046 Uiso 1 1 calc R U . . .
C8 C 0.3947(7) -0.0473(2) 0.1902(3) 0.0487(11) Uani 1 1 d . . . . .
C9 C 0.3018(7) -0.1187(2) 0.2293(3) 0.0530(13) Uani 1 1 d . . . . .
H9 H 0.2887 -0.1646 0.1936 0.064 Uiso 1 1 calc R U . . .
C10 C 0.1116(7) -0.0984(2) 0.2566(2) 0.0467(11) Uani 1 1 d . . . . .
H10A H 0.0689 -0.1441 0.2878 0.056 Uiso 1 1 calc R U . . .
H10B H 0.0273 -0.0951 0.2147 0.056 Uiso 1 1 calc R U . . .
C11 C 0.0978(6) -0.0179(2) 0.2994(2) 0.0385(10) Uani 1 1 d . . . . .
H11A H 0.1580 -0.0252 0.3469 0.046 Uiso 1 1 calc R U . . .
H11B H -0.0331 -0.0050 0.3082 0.046 Uiso 1 1 calc R U . . .
C7 C 0.2945(8) -0.0387(3) 0.1157(2) 0.0574(14) Uani 1 1 d . . . . .
H7A H 0.3511 -0.0781 0.0814 0.069 Uiso 1 1 calc R U . . .
H7B H 0.1649 -0.0555 0.1223 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2964(9) 0.0462(3) 0.0809(3) 0.0641(15) Uani 1 1 d . . . . .
H6A H 0.2380 0.0428 0.0326 0.077 Uiso 1 1 calc R U . . .
H6B H 0.4252 0.0639 0.0739 0.077 Uiso 1 1 calc R U . . .
C3 C -0.0368(6) 0.1592(2) 0.1817(2) 0.0416(9) Uani 1 1 d . . . . .
H3A H -0.1699 0.1493 0.1879 0.050 Uiso 1 1 calc R U . . .
H3B H 0.0043 0.2071 0.2106 0.050 Uiso 1 1 calc R U . . .
C13 C 0.0672(10) 0.2461(3) 0.0701(3) 0.0715(17) Uani 1 1 d . . . . .
H13A H 0.1215 0.2396 0.0220 0.107 Uiso 1 1 calc R U . . .
H13B H 0.1534 0.2755 0.1016 0.107 Uiso 1 1 calc R U . . .
H13C H -0.0471 0.2777 0.0663 0.107 Uiso 1 1 calc R U . . .
C15 C 0.5997(8) -0.0622(3) 0.1735(4) 0.0750(17) Uani 1 1 d . . . . .
H15A H 0.6698 -0.0623 0.2187 0.112 Uiso 1 1 calc R U . . .
H15B H 0.6453 -0.0183 0.1419 0.112 Uiso 1 1 calc R U . . .
H15C H 0.6140 -0.1155 0.1493 0.112 Uiso 1 1 calc R U . . .
C17 C 0.1582(7) 0.2316(2) 0.3965(3) 0.0510(12) Uani 1 1 d . . . . .
H17A H 0.2888 0.2409 0.3868 0.077 Uiso 1 1 calc R U . . .
H17B H 0.1416 0.2168 0.4474 0.077 Uiso 1 1 calc R U . . .
H17C H 0.0891 0.2819 0.3859 0.077 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 C9 2.199(5) . ?
S1 O1 1.423(3) . ?
S1 O2 1.424(3) . ?
S1 N2 1.559(3) . ?
S1 C18 1.816(5) . ?
F1 C18 1.312(6) . ?
F2 C18 1.296(7) . ?
F3 C18 1.305(7) . ?
N2 C16 1.323(5) . ?
N1 H1 0.8800 . ?
N1 C16 1.310(5) . ?
N1 C1 1.492(4) . ?
C16 C17 1.505(5) . ?
C1 C2 1.535(5) . ?
C1 C12 1.539(6) . ?
C1 C11 1.533(5) . ?
C2 H2 1.0000 . ?
C2 C5 1.539(6) . ?
C2 C3 1.543(5) . ?
C5 H5 1.0000 . ?
C5 C4 1.549(6) . ?
C5 C6 1.532(7) . ?
C4 C14 1.520(6) . ?
C4 C3 1.542(6) . ?
C4 C13 1.527(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C8 1.530(5) . ?
C8 C9 1.526(7) . ?
C8 C7 1.566(7) . ?
C8 C15 1.544(7) . ?
C9 H9 1.0000 . ?
C9 C10 1.512(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.531(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.520(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 116.9(2) . . ?
O1 S1 N2 108.98(18) . . ?
O1 S1 C18 104.2(3) . . ?
O2 S1 N2 118.31(19) . . ?
O2 S1 C18 104.9(2) . . ?
N2 S1 C18 101.2(2) . . ?
C16 N2 S1 126.5(2) . . ?
C16 N1 H1 116.2 . . ?
C16 N1 C1 127.6(3) . . ?
C1 N1 H1 116.2 . . ?
F1 C18 S1 111.6(3) . . ?
F2 C18 S1 110.9(4) . . ?
F2 C18 F1 107.6(5) . . ?
F2 C18 F3 107.9(5) . . ?
F3 C18 S1 110.4(4) . . ?
F3 C18 F1 108.2(5) . . ?
N2 C16 C17 125.9(3) . . ?
N1 C16 N2 118.6(3) . . ?
N1 C16 C17 115.5(3) . . ?
N1 C1 C2 111.3(3) . . ?
N1 C1 C12 104.3(3) . . ?
N1 C1 C11 110.1(3) . . ?
C2 C1 C12 109.2(3) . . ?
C11 C1 C2 113.4(3) . . ?
C11 C1 C12 108.2(3) . . ?
C1 C2 H2 107.2 . . ?
C1 C2 C5 117.8(3) . . ?
C1 C2 C3 127.8(3) . . ?
C5 C2 H2 107.2 . . ?
C5 C2 C3 87.4(3) . . ?
C3 C2 H2 107.2 . . ?
C2 C5 H5 107.4 . . ?
C2 C5 C4 88.0(3) . . ?
C4 C5 H5 107.4 . . ?
C6 C5 C2 118.5(3) . . ?
C6 C5 H5 107.4 . . ?
C6 C5 C4 125.9(4) . . ?
C14 C4 C5 114.1(4) . . ?
C14 C4 C3 112.2(4) . . ?
C14 C4 C13 109.6(4) . . ?
C3 C4 C5 87.0(3) . . ?
C13 C4 C5 115.8(4) . . ?
C13 C4 C3 116.7(3) . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C12 H12A 108.6 . . ?
C1 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C8 C12 C1 114.7(3) . . ?
C8 C12 H12A 108.6 . . ?
C8 C12 H12B 108.6 . . ?
C12 C8 C7 114.6(4) . . ?
C12 C8 C15 107.1(4) . . ?
C9 C8 C12 108.5(4) . . ?
C9 C8 C7 106.2(4) . . ?
C9 C8 C15 113.9(4) . . ?
C15 C8 C7 106.8(5) . . ?
I1 C9 H9 107.2 . . ?
C8 C9 I1 113.1(3) . . ?
C8 C9 H9 107.2 . . ?
C10 C9 I1 108.2(3) . . ?
C10 C9 C8 113.5(3) . . ?
C10 C9 H9 107.2 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C9 C10 C11 114.8(4) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C1 C11 H11A 109.1 . . ?
C1 C11 H11B 109.1 . . ?
C10 C11 C1 112.4(3) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C8 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C6 C7 C8 116.7(4) . . ?
C6 C7 H7A 108.1 . . ?
C6 C7 H7B 108.1 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 C5 112.5(4) . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C2 C3 H3A 114.0 . . ?
C2 C3 H3B 114.0 . . ?
C4 C3 C2 88.1(3) . . ?
C4 C3 H3A 114.0 . . ?
C4 C3 H3B 114.0 . . ?
H3A C3 H3B 111.2 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C9 C10 C11 77.0(4) . . . . ?
S1 N2 C16 N1 177.1(3) . . . . ?
S1 N2 C16 C17 -5.0(6) . . . . ?
O1 S1 N2 C16 144.1(3) . . . . ?
O1 S1 C18 F1 55.0(5) . . . . ?
O1 S1 C18 F2 175.0(4) . . . . ?
O1 S1 C18 F3 -65.5(5) . . . . ?
O2 S1 N2 C16 7.4(4) . . . . ?
O2 S1 C18 F1 178.3(4) . . . . ?
O2 S1 C18 F2 -61.7(5) . . . . ?
O2 S1 C18 F3 57.9(5) . . . . ?
N2 S1 C18 F1 -58.1(5) . . . . ?
N2 S1 C18 F2 61.8(4) . . . . ?
N2 S1 C18 F3 -178.6(4) . . . . ?
N1 C1 C2 C5 91.5(4) . . . . ?
N1 C1 C2 C3 -18.6(5) . . . . ?
N1 C1 C12 C8 175.6(3) . . . . ?
N1 C1 C11 C10 -165.3(3) . . . . ?
C18 S1 N2 C16 -106.4(4) . . . . ?
C16 N1 C1 C2 69.9(5) . . . . ?
C16 N1 C1 C12 -172.5(3) . . . . ?
C16 N1 C1 C11 -56.7(5) . . . . ?
C1 N1 C16 N2 -2.4(6) . . . . ?
C1 N1 C16 C17 179.5(3) . . . . ?
C1 C2 C5 C4 -154.9(3) . . . . ?
C1 C2 C5 C6 74.6(5) . . . . ?
C1 C2 C3 C4 146.7(4) . . . . ?
C1 C12 C8 C9 -57.7(5) . . . . ?
C1 C12 C8 C7 60.8(5) . . . . ?
C1 C12 C8 C15 179.0(4) . . . . ?
C2 C1 C12 C8 -65.4(4) . . . . ?
C2 C1 C11 C10 69.4(4) . . . . ?
C2 C5 C4 C14 -90.1(4) . . . . ?
C2 C5 C4 C3 22.9(3) . . . . ?
C2 C5 C4 C13 141.3(4) . . . . ?
C2 C5 C6 C7 -9.6(7) . . . . ?
C5 C2 C3 C4 23.0(3) . . . . ?
C5 C4 C3 C2 -22.9(3) . . . . ?
C4 C5 C6 C7 -119.8(5) . . . . ?
C14 C4 C3 C2 92.0(4) . . . . ?
C12 C1 C2 C5 -23.1(4) . . . . ?
C12 C1 C2 C3 -133.2(4) . . . . ?
C12 C1 C11 C10 -51.9(4) . . . . ?
C12 C8 C9 I1 -72.7(4) . . . . ?
C12 C8 C9 C10 51.1(5) . . . . ?
C12 C8 C7 C6 33.9(6) . . . . ?
C8 C9 C10 C11 -49.4(5) . . . . ?
C8 C7 C6 C5 -63.3(7) . . . . ?
C9 C8 C7 C6 153.6(4) . . . . ?
C9 C10 C11 C1 49.7(5) . . . . ?
C11 C1 C2 C5 -143.8(3) . . . . ?
C11 C1 C2 C3 106.1(4) . . . . ?
C11 C1 C12 C8 58.4(5) . . . . ?
C7 C8 C9 I1 163.7(3) . . . . ?
C7 C8 C9 C10 -72.6(4) . . . . ?
C6 C5 C4 C14 34.3(6) . . . . ?
C6 C5 C4 C3 147.3(4) . . . . ?
C6 C5 C4 C13 -94.3(5) . . . . ?
C3 C2 C5 C4 -22.9(3) . . . . ?
C3 C2 C5 C6 -153.4(4) . . . . ?
C13 C4 C3 C2 -140.4(5) . . . . ?
C15 C8 C9 I1 46.5(5) . . . . ?
C15 C8 C9 C10 170.3(4) . . . . ?
C15 C8 C7 C6 -84.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 2430945'
loop_
_audit_author_name
_audit_author_address
'Borodina Tatiana'
;Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Science
Russia
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2025-02-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
N-(6-bromo-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-yl)-N'-((trifluoromethyl)sulfonyl)acetimidamide
_chemical_formula_moiety         'C18 H28 Br F3 N2 O2 S'
_chemical_formula_sum            'C18 H28 Br F3 N2 O2 S'
_chemical_formula_weight         473.39
_chemical_absolute_configuration .
_chemical_melting_point          444.2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.3387(5)
_cell_length_b                   8.9043(6)
_cell_length_c                   32.227(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2105.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9756
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      61.18
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.705
_shelx_estimated_absorpt_T_min   0.383
_exptl_absorpt_coefficient_mu    3.961
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.4661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1525 before and 0.0740 after correction.
The Ratio of minimum to maximum transmission is 0.6198.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.095
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.859
_diffrn_reflns_Laue_measured_fraction_max 1.001
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            31942
_diffrn_reflns_point_group_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         61.292
_diffrn_reflns_theta_min         2.742
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.859
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3120
_reflns_number_total             3241
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (BRUKER, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.32B (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1258 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.027(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+0.9429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0722
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C9A(H9A)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C5(H5A,H5B), C4(H4A,H4B), C2(H2A,H2B), C9(H9B,H9C), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.039
;
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
Br1 Br 0.49064(8) -0.33968(5) 0.05884(2) 0.06744(18) Uani 1 1 d . . . . .
S1 S 0.32731(11) -0.17421(11) 0.22139(3) 0.0386(2) Uani 1 1 d . . . . .
F1 F 0.4159(5) -0.4255(4) 0.18548(17) 0.1215(16) Uani 1 1 d . . . . .
F2 F 0.2289(6) -0.2928(5) 0.15098(11) 0.1095(13) Uani 1 1 d . . . . .
F3 F 0.1394(4) -0.4123(4) 0.20427(13) 0.0989(12) Uani 1 1 d . . . . .
O1 O 0.1707(4) -0.0807(3) 0.21576(11) 0.0616(8) Uani 1 1 d . . . . .
O2 O 0.3536(4) -0.2350(5) 0.26150(9) 0.0701(10) Uani 1 1 d . . . . .
N2 N 0.4937(4) -0.0982(3) 0.19951(9) 0.0367(6) Uani 1 1 d . . . . .
N1 N 0.7927(4) -0.0563(3) 0.18756(8) 0.0326(6) Uani 1 1 d . . . . .
H1 H 0.9065 -0.0844 0.1914 0.039 Uiso 1 1 calc R U . . .
C16 C 0.2764(6) -0.3354(6) 0.18871(16) 0.0636(12) Uani 1 1 d . . . . .
C14 C 0.6681(5) -0.1305(4) 0.20824(9) 0.0331(8) Uani 1 1 d . . . . .
C3 C 0.7626(4) 0.0686(4) 0.15872(10) 0.0308(7) Uani 1 1 d . . . . .
H3 H 0.6536 0.1268 0.1681 0.037 Uiso 1 1 calc R U . . .
C3A C 0.7372(5) 0.0268(4) 0.11201(9) 0.0306(7) Uani 1 1 d . . . . .
C10 C 0.5365(5) 0.0102(4) 0.09925(9) 0.0339(7) Uani 1 1 d . . . . .
H10A H 0.4684 0.1014 0.1076 0.041 Uiso 1 1 calc R U . . .
H10B H 0.4823 -0.0767 0.1139 0.041 Uiso 1 1 calc R U . . .
C7 C 0.5188(5) -0.0127(4) 0.05190(10) 0.0398(8) Uani 1 1 d . . . . .
C13 C 0.3182(6) -0.0180(6) 0.03967(13) 0.0556(11) Uani 1 1 d . . . . .
H13A H 0.2562 -0.0962 0.0558 0.083 Uiso 1 1 calc R U . . .
H13B H 0.3078 -0.0408 0.0100 0.083 Uiso 1 1 calc R U . . .
H13C H 0.2615 0.0795 0.0454 0.083 Uiso 1 1 calc R U . . .
C6 C 0.6210(5) -0.1576(5) 0.03964(11) 0.0469(9) Uani 1 1 d . . . . .
H6 H 0.6259 -0.1615 0.0087 0.056 Uiso 1 1 calc R U . . .
C5 C 0.8156(6) -0.1621(6) 0.05546(11) 0.0521(10) Uani 1 1 d . . . . .
H5A H 0.8904 -0.0919 0.0388 0.063 Uiso 1 1 calc R U . . .
H5B H 0.8650 -0.2645 0.0513 0.063 Uiso 1 1 calc R U . . .
C4 C 0.8339(5) -0.1205(4) 0.10144(11) 0.0410(8) Uani 1 1 d . . . . .
H4A H 0.7820 -0.2022 0.1186 0.049 Uiso 1 1 calc R U . . .
H4B H 0.9647 -0.1112 0.1085 0.049 Uiso 1 1 calc R U . . .
C9A C 0.8239(5) 0.1651(5) 0.08893(10) 0.0408(8) Uani 1 1 d . . . . .
H9A H 0.9309 0.1264 0.0730 0.049 Uiso 1 1 calc R U . . .
C1 C 0.8996(6) 0.2751(5) 0.12210(12) 0.0451(9) Uani 1 1 d . . . . .
C2 C 0.9285(5) 0.1723(5) 0.15934(11) 0.0400(8) Uani 1 1 d . . . . .
H2A H 0.9333 0.2309 0.1854 0.048 Uiso 1 1 calc R U . . .
H2B H 1.0427 0.1142 0.1564 0.048 Uiso 1 1 calc R U . . .
C15 C 0.7363(5) -0.2430(6) 0.23904(14) 0.0559(12) Uani 1 1 d . . . . .
H15A H 0.7093 -0.3446 0.2291 0.084 Uiso 1 1 calc R U . . .
H15B H 0.6760 -0.2266 0.2658 0.084 Uiso 1 1 calc R U . . .
H15C H 0.8683 -0.2313 0.2424 0.084 Uiso 1 1 calc R U . . .
C11 C 1.0791(7) 0.3462(6) 0.10775(15) 0.0674(13) Uani 1 1 d . . . . .
H11A H 1.0568 0.4085 0.0832 0.101 Uiso 1 1 calc R U . . .
H11B H 1.1665 0.2668 0.1008 0.101 Uiso 1 1 calc R U . . .
H11C H 1.1289 0.4087 0.1301 0.101 Uiso 1 1 calc R U . . .
C12 C 0.7669(8) 0.4010(5) 0.13433(16) 0.0656(13) Uani 1 1 d . . . . .
H12A H 0.8146 0.4546 0.1586 0.098 Uiso 1 1 calc R U . . .
H12B H 0.6479 0.3574 0.1411 0.098 Uiso 1 1 calc R U . . .
H12C H 0.7535 0.4712 0.1111 0.098 Uiso 1 1 calc R U . . .
C9 C 0.6936(7) 0.2358(5) 0.05738(13) 0.0578(11) Uani 1 1 d . . . . .
H9B H 0.5932 0.2869 0.0723 0.069 Uiso 1 1 calc R U . . .
H9C H 0.7598 0.3123 0.0410 0.069 Uiso 1 1 calc R U . . .
C8 C 0.6145(7) 0.1186(5) 0.02831(12) 0.0554(12) Uani 1 1 d . . . . .
H8A H 0.7135 0.0771 0.0109 0.066 Uiso 1 1 calc R U . . .
H8B H 0.5251 0.1674 0.0097 0.066 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
Br1 C6 1.981(5) . ?
S1 O1 1.431(3) . ?
S1 O2 1.415(3) . ?
S1 N2 1.564(3) . ?
S1 C16 1.819(5) . ?
F1 C16 1.304(6) . ?
F2 C16 1.321(6) . ?
F3 C16 1.316(5) . ?
N2 C14 1.342(5) . ?
N1 H1 0.8800 . ?
N1 C14 1.310(4) . ?
N1 C3 1.467(4) . ?
C14 C15 1.496(5) . ?
C3 H3 1.0000 . ?
C3 C3A 1.562(4) . ?
C3 C2 1.528(5) . ?
C3A C10 1.536(5) . ?
C3A C4 1.530(5) . ?
C3A C9A 1.573(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C7 1.545(4) . ?
C7 C13 1.525(6) . ?
C7 C6 1.545(6) . ?
C7 C8 1.561(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C5 1.517(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.533(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C9A H9A 1.0000 . ?
C9A C1 1.553(6) . ?
C9A C9 1.531(6) . ?
C1 C2 1.524(6) . ?
C1 C11 1.533(6) . ?
C1 C12 1.536(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9 H9B 0.9900 . ?
C9 H9C 0.9900 . ?
C9 C8 1.518(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 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 N2 108.55(17) . . ?
O1 S1 C16 102.8(2) . . ?
O2 S1 O1 116.6(2) . . ?
O2 S1 N2 118.09(16) . . ?
O2 S1 C16 104.8(2) . . ?
N2 S1 C16 103.93(18) . . ?
C14 N2 S1 123.9(2) . . ?
C14 N1 H1 116.6 . . ?
C14 N1 C3 126.8(3) . . ?
C3 N1 H1 116.6 . . ?
F1 C16 S1 111.7(3) . . ?
F1 C16 F2 108.1(5) . . ?
F1 C16 F3 108.1(5) . . ?
F2 C16 S1 111.1(4) . . ?
F3 C16 S1 110.3(3) . . ?
F3 C16 F2 107.4(4) . . ?
N2 C14 C15 127.0(3) . . ?
N1 C14 N2 116.8(3) . . ?
N1 C14 C15 116.2(3) . . ?
N1 C3 H3 108.7 . . ?
N1 C3 C3A 116.6(3) . . ?
N1 C3 C2 109.3(3) . . ?
C3A C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C2 C3 C3A 104.6(3) . . ?
C3 C3A C9A 102.8(3) . . ?
C10 C3A C3 113.3(3) . . ?
C10 C3A C9A 109.6(3) . . ?
C4 C3A C3 111.3(3) . . ?
C4 C3A C10 107.6(3) . . ?
C4 C3A C9A 112.2(3) . . ?
C3A C10 H10A 109.4 . . ?
C3A C10 H10B 109.4 . . ?
C3A C10 C7 111.0(3) . . ?
H10A C10 H10B 108.0 . . ?
C7 C10 H10A 109.4 . . ?
C7 C10 H10B 109.4 . . ?
C10 C7 C8 110.1(3) . . ?
C13 C7 C10 109.9(3) . . ?
C13 C7 C6 112.1(3) . . ?
C13 C7 C8 109.4(3) . . ?
C6 C7 C10 108.8(3) . . ?
C6 C7 C8 106.4(3) . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Br1 C6 H6 107.5 . . ?
C7 C6 Br1 111.7(3) . . ?
C7 C6 H6 107.5 . . ?
C5 C6 Br1 109.2(3) . . ?
C5 C6 C7 113.2(4) . . ?
C5 C6 H6 107.5 . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C6 C5 C4 113.6(3) . . ?
H5A C5 H5B 107.7 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C3A C4 C5 112.5(3) . . ?
C3A C4 H4A 109.1 . . ?
C3A C4 H4B 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C3A C9A H9A 106.9 . . ?
C1 C9A C3A 108.2(3) . . ?
C1 C9A H9A 106.9 . . ?
C9 C9A C3A 112.5(3) . . ?
C9 C9A H9A 106.9 . . ?
C9 C9A C1 114.9(4) . . ?
C2 C1 C9A 102.3(3) . . ?
C2 C1 C11 111.5(4) . . ?
C2 C1 C12 108.9(3) . . ?
C11 C1 C9A 111.1(3) . . ?
C11 C1 C12 108.7(4) . . ?
C12 C1 C9A 114.2(4) . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 C3 104.0(3) . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9A C9 H9B 109.3 . . ?
C9A C9 H9C 109.3 . . ?
H9B C9 H9C 108.0 . . ?
C8 C9 C9A 111.5(4) . . ?
C8 C9 H9B 109.3 . . ?
C8 C9 H9C 109.3 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 C7 112.7(3) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 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
Br1 C6 C5 C4 -77.1(4) . . . . ?
S1 N2 C14 N1 -179.4(3) . . . . ?
S1 N2 C14 C15 0.9(5) . . . . ?
O1 S1 N2 C14 160.2(3) . . . . ?
O1 S1 C16 F1 171.5(4) . . . . ?
O1 S1 C16 F2 50.7(4) . . . . ?
O1 S1 C16 F3 -68.2(4) . . . . ?
O2 S1 N2 C14 24.5(4) . . . . ?
O2 S1 C16 F1 -66.1(4) . . . . ?
O2 S1 C16 F2 173.1(3) . . . . ?
O2 S1 C16 F3 54.1(4) . . . . ?
N2 S1 C16 F1 58.4(4) . . . . ?
N2 S1 C16 F2 -62.4(4) . . . . ?
N2 S1 C16 F3 178.7(3) . . . . ?
N1 C3 C3A C10 94.5(3) . . . . ?
N1 C3 C3A C4 -27.0(4) . . . . ?
N1 C3 C3A C9A -147.3(3) . . . . ?
N1 C3 C2 C1 168.0(3) . . . . ?
C16 S1 N2 C14 -91.0(3) . . . . ?
C14 N1 C3 C3A -91.5(4) . . . . ?
C14 N1 C3 C2 150.3(3) . . . . ?
C3 N1 C14 N2 6.4(5) . . . . ?
C3 N1 C14 C15 -173.9(3) . . . . ?
C3 C3A C10 C7 173.4(3) . . . . ?
C3 C3A C4 C5 -178.4(3) . . . . ?
C3 C3A C9A C1 1.9(4) . . . . ?
C3 C3A C9A C9 -126.2(3) . . . . ?
C3A C3 C2 C1 42.4(4) . . . . ?
C3A C10 C7 C13 -176.1(3) . . . . ?
C3A C10 C7 C6 60.7(4) . . . . ?
C3A C10 C7 C8 -55.6(4) . . . . ?
C3A C9A C1 C2 23.2(4) . . . . ?
C3A C9A C1 C11 142.3(4) . . . . ?
C3A C9A C1 C12 -94.3(4) . . . . ?
C3A C9A C9 C8 -51.0(5) . . . . ?
C10 C3A C4 C5 56.8(4) . . . . ?
C10 C3A C9A C1 122.7(3) . . . . ?
C10 C3A C9A C9 -5.4(4) . . . . ?
C10 C7 C6 Br1 71.5(3) . . . . ?
C10 C7 C6 C5 -52.1(4) . . . . ?
C10 C7 C8 C9 -1.9(5) . . . . ?
C7 C6 C5 C4 47.9(5) . . . . ?
C13 C7 C6 Br1 -50.3(4) . . . . ?
C13 C7 C6 C5 -173.9(3) . . . . ?
C13 C7 C8 C9 119.0(4) . . . . ?
C6 C7 C8 C9 -119.6(4) . . . . ?
C6 C5 C4 C3A -50.6(5) . . . . ?
C4 C3A C10 C7 -63.1(4) . . . . ?
C4 C3A C9A C1 -117.8(3) . . . . ?
C4 C3A C9A C9 114.1(4) . . . . ?
C9A C3A C10 C7 59.2(4) . . . . ?
C9A C3A C4 C5 -63.9(4) . . . . ?
C9A C1 C2 C3 -40.0(4) . . . . ?
C9A C9 C8 C7 55.1(5) . . . . ?
C1 C9A C9 C8 -175.5(3) . . . . ?
C2 C3 C3A C10 -144.7(3) . . . . ?
C2 C3 C3A C4 93.8(3) . . . . ?
C2 C3 C3A C9A -26.5(3) . . . . ?
C11 C1 C2 C3 -158.8(3) . . . . ?
C12 C1 C2 C3 81.3(4) . . . . ?
C9 C9A C1 C2 149.9(3) . . . . ?
C9 C9A C1 C11 -91.0(4) . . . . ?
C9 C9A C1 C12 32.4(5) . . . . ?
C8 C7 C6 Br1 -169.8(2) . . . . ?
C8 C7 C6 C5 66.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_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_3h
_database_code_depnum_ccdc_archive 'CCDC 2430948'
loop_
_audit_author_name
_audit_author_address
'Borodina Tatiana'
;Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Science
Russia
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2025-02-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
N-(6-bromo-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-yl)-N'-((4-(trifluoromethyl)phenyl)sulfonyl)acetimidamide
_chemical_formula_moiety         'C24 H32 Br F3 N2 O2 S'
_chemical_formula_sum            'C24 H32 Br F3 N2 O2 S'
_chemical_formula_weight         549.48
_chemical_absolute_configuration .
_chemical_melting_point          480.3
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.3167(13)
_cell_length_b                   10.7257(14)
_cell_length_c                   11.5944(14)
_cell_angle_alpha                90.113(4)
_cell_angle_beta                 93.196(4)
_cell_angle_gamma                93.055(4)
_cell_volume                     1279.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.25
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.425
_shelx_estimated_absorpt_T_min   0.423
_exptl_absorpt_coefficient_mu    1.733
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.2883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1427 before and 0.0984 after correction.
The Ratio of minimum to maximum transmission is 0.3865.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.595
_exptl_crystal_size_min          0.595
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            61939
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.760
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.984
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                9899
_reflns_number_total             14380
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (BRUKER, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.32B (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 3735 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.094(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         14380
_refine_ls_number_restraints     399
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0797P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1505
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F102) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F101) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F103) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F101)
\\sim Ueq, Uanis(F102) \\sim Ueq, Uanis(F103) \\sim Ueq: with sigma of 0.05 and
sigma for terminal atoms of 0.1
Uanis(C122) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C119) \\sim Ueq, Uanis(Br1A) \\sim Ueq, Uanis(C106) \\sim Ueq,
Uanis(C107) \\sim Ueq, Uanis(C105) \\sim Ueq, Uanis(C110) \\sim Ueq,
Uanis(C108) \\sim Ueq, Uanis(C113) \\sim Ueq, Uanis(C104) \\sim Ueq,
Uanis(C13A) \\sim Ueq, Uanis(C109) \\sim Ueq, Uanis(C103) \\sim Ueq,
Uanis(C19A) \\sim Ueq, Uanis(N101) \\sim Ueq, Uanis(C102) \\sim Ueq,
Uanis(C101) \\sim Ueq, Uanis(C114) \\sim Ueq, Uanis(C112) \\sim Ueq,
Uanis(C111) \\sim Ueq, Uanis(N102) \\sim Ueq, Uanis(C115) \\sim Ueq,
Uanis(S101) \\sim Ueq, Uanis(O102) \\sim Ueq, Uanis(O101) \\sim Ueq,
Uanis(C116) \\sim Ueq, Uanis(C121) \\sim Ueq, Uanis(C117) \\sim Ueq,
Uanis(C120) \\sim Ueq, Uanis(C118) \\sim Ueq, Uanis(C122) \\sim Ueq,
Uanis(F101) \\sim Ueq, Uanis(F103) \\sim Ueq, Uanis(F102) \\sim Ueq, Uanis(Br1)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C5) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C4)
\\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C3) \\sim Ueq,
Uanis(C9A) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(N2) \\sim Ueq,
Uanis(C15) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O1) \\sim
Ueq, Uanis(C16) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(C20) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq,
Uanis(C1) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(F103) \\sim Ueq, Uanis(F102) \\sim Ueq, Uanis(F101) \\sim Ueq,
Uanis(C122) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C122) \\sim Ueq, Uanis(F102) \\sim Ueq, Uanis(F101) \\sim Ueq,
Uanis(F103) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C9A(H9A), C103(H103), C106(H106), C19A(H19A)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B), C5(H5A,H5B), C4(H4A,H4B), C2(H2A,H2B), C9(H9B,
 H9C), C110(H11G,H11H), C105(H10C,H10D), C104(H10E,H10F), C108(H10G,H10H),
 C109(H10I,H10J), C102(H10K,H10L)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C20(H20), C21(H21), N1(H1), C17(H17), N101(H101), C121(H121),
 C120(H120), C117(H117), C118(H118)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C113(H11D,H11E,H11F), C115(H11I,H11J,H11K), C112(H11L,H11M,H11N),
 C111(H11O,H11P,H11Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.041
;
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
Br1 Br 0.01374(7) 0.23993(8) 0.23149(8) 0.0936(3) Uani 1 1 d . U . . .
Br1A Br 0.98518(8) 0.75989(10) 0.77721(10) 0.1073(3) Uani 1 1 d . U . . .
C22 C -0.1957(8) 0.5859(9) 0.1596(10) 0.093(3) Uani 1 1 d . U . . .
S1 S 0.38356(10) 0.65964(9) 0.14785(9) 0.0353(2) Uani 1 1 d . U . . .
S101 S 0.60699(10) 0.33699(9) 0.65450(8) 0.0341(2) Uani 1 1 d . U . . .
F3 F -0.2579(6) 0.6504(10) 0.0878(12) 0.211(5) Uani 1 1 d . U . . .
C13 C 0.0971(7) 0.1648(7) -0.0243(7) 0.079(2) Uani 1 1 d . U . . .
H13A H 0.0709 0.2497 -0.0101 0.119 Uiso 1 1 calc R U . . .
H13B H 0.0199 0.1074 -0.0305 0.119 Uiso 1 1 calc R U . . .
H13C H 0.1422 0.1630 -0.0964 0.119 Uiso 1 1 calc R U . . .
F1 F -0.2383(7) 0.4793(7) 0.1368(14) 0.225(5) Uani 1 1 d . U . . .
F2 F -0.2407(7) 0.6078(19) 0.2486(11) 0.290(8) Uani 1 1 d . U . . .
O2 O 0.4221(4) 0.7571(3) 0.2291(3) 0.0479(8) Uani 1 1 d . U . . .
O1 O 0.4130(4) 0.6821(3) 0.0298(3) 0.0562(9) Uani 1 1 d . U . . .
O102 O 0.5919(4) 0.2426(3) 0.7408(3) 0.0486(8) Uani 1 1 d . U . . .
O101 O 0.5529(4) 0.3061(3) 0.5408(3) 0.0484(8) Uani 1 1 d . U . . .
C18 C 0.0159(7) 0.6635(8) 0.2420(6) 0.0778(19) Uani 1 1 d . U . . .
H18 H -0.0279 0.6930 0.3057 0.093 Uiso 1 1 calc R U . . .
C19 C -0.0525(6) 0.6054(6) 0.1561(6) 0.0659(16) Uani 1 1 d . U . . .
C20 C 0.0127(8) 0.5608(8) 0.0620(7) 0.087(2) Uani 1 1 d . U . . .
H20 H -0.0359 0.5187 0.0003 0.105 Uiso 1 1 calc R U . . .
C21 C 0.1442(7) 0.5771(7) 0.0581(5) 0.0707(17) Uani 1 1 d . U . . .
H21 H 0.1879 0.5465 -0.0053 0.085 Uiso 1 1 calc R U . . .
C16 C 0.2127(5) 0.6393(4) 0.1487(4) 0.0389(9) Uani 1 1 d . U . . .
N2 N 0.4334(4) 0.5248(3) 0.1799(3) 0.0331(7) Uani 1 1 d . U . . .
C14 C 0.4611(4) 0.4900(3) 0.2859(3) 0.0302(8) Uani 1 1 d . U . . .
N1 N 0.4950(3) 0.3745(3) 0.3039(3) 0.0311(7) Uani 1 1 d . U . . .
H1 H 0.5107 0.3521 0.3761 0.037 Uiso 1 1 calc R U . . .
C3 C 0.5089(4) 0.2805(3) 0.2148(3) 0.0286(7) Uani 1 1 d . U . . .
H3 H 0.5250 0.3239 0.1403 0.034 Uiso 1 1 calc R U . . .
C3A C 0.3925(4) 0.1855(3) 0.1950(3) 0.0325(8) Uani 1 1 d . U . . .
C10 C 0.2947(5) 0.2277(4) 0.1014(4) 0.0402(10) Uani 1 1 d . U . . .
H10A H 0.3399 0.2477 0.0300 0.048 Uiso 1 1 calc R U . . .
H10B H 0.2549 0.3042 0.1273 0.048 Uiso 1 1 calc R U . . .
C7 C 0.1886(5) 0.1247(5) 0.0760(5) 0.0514(12) Uani 1 1 d . U . . .
C8 C 0.2516(6) 0.0005(5) 0.0404(5) 0.0605(15) Uani 1 1 d . U . . .
H8A H 0.2259 -0.0667 0.0943 0.073 Uiso 1 1 calc R U . . .
H8B H 0.2169 -0.0246 -0.0381 0.073 Uiso 1 1 calc R U . . .
C6 C 0.1166(6) 0.0981(5) 0.1860(5) 0.0591(14) Uani 1 1 d . U . . .
H6 H 0.0549 0.0241 0.1706 0.071 Uiso 1 1 calc R U . . .
C5 C 0.2083(6) 0.0672(5) 0.2901(5) 0.0557(13) Uani 1 1 d . U . . .
H5A H 0.1589 0.0641 0.3609 0.067 Uiso 1 1 calc R U . . .
H5B H 0.2424 -0.0162 0.2785 0.067 Uiso 1 1 calc R U . . .
C4 C 0.3212(5) 0.1635(4) 0.3059(4) 0.0391(9) Uani 1 1 d . U . . .
H4A H 0.3833 0.1350 0.3673 0.047 Uiso 1 1 calc R U . . .
H4B H 0.2882 0.2433 0.3317 0.047 Uiso 1 1 calc R U . . .
C17 C 0.1499(6) 0.6824(6) 0.2415(5) 0.0624(15) Uani 1 1 d . U . . .
H17 H 0.1974 0.7244 0.3039 0.075 Uiso 1 1 calc R U . . .
C15 C 0.4615(6) 0.5677(4) 0.3935(4) 0.0521(13) Uani 1 1 d . U . . .
H15A H 0.5285 0.6358 0.3906 0.078 Uiso 1 1 calc R U . . .
H15B H 0.4800 0.5156 0.4611 0.078 Uiso 1 1 calc R U . . .
H15C H 0.3762 0.6027 0.3991 0.078 Uiso 1 1 calc R U . . .
C2 C 0.6235(4) 0.2006(4) 0.2463(4) 0.0350(9) Uani 1 1 d . U . . .
H2A H 0.6202 0.1699 0.3266 0.042 Uiso 1 1 calc R U . . .
H2B H 0.7072 0.2483 0.2378 0.042 Uiso 1 1 calc R U . . .
C1 C 0.6059(4) 0.0925(4) 0.1594(4) 0.0366(9) Uani 1 1 d . U . . .
C9A C 0.4579(5) 0.0644(4) 0.1553(4) 0.0360(9) Uani 1 1 d . U . . .
H9A H 0.4411 -0.0007 0.2151 0.043 Uiso 1 1 calc R U . . .
C9 C 0.3956(6) 0.0131(4) 0.0413(4) 0.0506(12) Uani 1 1 d . U . . .
H9B H 0.4212 0.0695 -0.0220 0.061 Uiso 1 1 calc R U . . .
H9C H 0.4294 -0.0697 0.0262 0.061 Uiso 1 1 calc R U . . .
C11 C 0.6795(6) -0.0202(5) 0.2011(5) 0.0548(13) Uani 1 1 d . U . . .
H11A H 0.6496 -0.0469 0.2764 0.082 Uiso 1 1 calc R U . . .
H11B H 0.7729 0.0026 0.2084 0.082 Uiso 1 1 calc R U . . .
H11C H 0.6633 -0.0888 0.1453 0.082 Uiso 1 1 calc R U . . .
C12 C 0.6569(6) 0.1347(5) 0.0426(4) 0.0530(12) Uani 1 1 d . U . . .
H12A H 0.6478 0.0645 -0.0121 0.080 Uiso 1 1 calc R U . . .
H12B H 0.7487 0.1628 0.0533 0.080 Uiso 1 1 calc R U . . .
H12C H 0.6065 0.2035 0.0122 0.080 Uiso 1 1 calc R U . . .
C113 C 0.8984(7) 0.8289(7) 0.5144(7) 0.078(2) Uani 1 1 d . U . . .
H11D H 0.9233 0.7436 0.5308 0.118 Uiso 1 1 calc R U . . .
H11E H 0.9764 0.8853 0.5164 0.118 Uiso 1 1 calc R U . . .
H11F H 0.8536 0.8315 0.4377 0.118 Uiso 1 1 calc R U . . .
C107 C 0.8075(6) 0.8701(5) 0.6055(5) 0.0566(13) Uani 1 1 d . U . . .
C110 C 0.7009(5) 0.7677(4) 0.6213(4) 0.0417(10) Uani 1 1 d . U . . .
H11G H 0.7407 0.6916 0.6518 0.050 Uiso 1 1 calc R U . . .
H11H H 0.6560 0.7466 0.5455 0.050 Uiso 1 1 calc R U . . .
C13A C 0.6020(4) 0.8103(3) 0.7047(3) 0.0321(8) Uani 1 1 d . U . . .
C103 C 0.4859(4) 0.7167(3) 0.7152(3) 0.0295(8) Uani 1 1 d . U . . .
H103 H 0.4680 0.6734 0.6392 0.035 Uiso 1 1 calc R U . . .
N101 N 0.4989(4) 0.6226(3) 0.8044(3) 0.0328(7) Uani 1 1 d . U . . .
H101 H 0.4851 0.6453 0.8755 0.039 Uiso 1 1 calc R U . . .
C114 C 0.5295(4) 0.5063(4) 0.7887(3) 0.0320(8) Uani 1 1 d . U . . .
N102 N 0.5606(4) 0.4716(3) 0.6853(3) 0.0341(7) Uani 1 1 d . U . . .
C116 C 0.7753(5) 0.3648(4) 0.6422(4) 0.0403(10) Uani 1 1 d . U . . .
C121 C 0.8565(7) 0.3473(8) 0.7344(6) 0.083(2) Uani 1 1 d . U . . .
H121 H 0.8229 0.3215 0.8057 0.100 Uiso 1 1 calc R U . . .
C120 C 0.9901(9) 0.3669(11) 0.7256(10) 0.107(3) Uani 1 1 d . U . . .
H120 H 1.0474 0.3534 0.7908 0.128 Uiso 1 1 calc R U . . .
C119 C 1.0388(7) 0.4053(7) 0.6244(9) 0.080(2) Uani 1 1 d . U . . .
C106 C 0.8793(6) 0.8984(6) 0.7226(6) 0.0672(16) Uani 1 1 d . U . . .
H106 H 0.9397 0.9732 0.7126 0.081 Uiso 1 1 calc R U . . .
C105 C 0.7886(6) 0.9291(6) 0.8166(5) 0.0587(14) Uani 1 1 d . U . . .
H10C H 0.8386 0.9332 0.8920 0.070 Uiso 1 1 calc R U . . .
H10D H 0.7545 1.0124 0.8014 0.070 Uiso 1 1 calc R U . . .
C104 C 0.6758(5) 0.8341(4) 0.8235(4) 0.0433(10) Uani 1 1 d . U . . .
H10E H 0.6147 0.8639 0.8790 0.052 Uiso 1 1 calc R U . . .
H10F H 0.7087 0.7544 0.8529 0.052 Uiso 1 1 calc R U . . .
C108 C 0.7452(6) 0.9927(5) 0.5650(6) 0.0628(16) Uani 1 1 d . U . . .
H10G H 0.7704 1.0595 0.6222 0.075 Uiso 1 1 calc R U . . .
H10H H 0.7806 1.0184 0.4905 0.075 Uiso 1 1 calc R U . . .
C109 C 0.5988(6) 0.9805(5) 0.5501(5) 0.0563(13) Uani 1 1 d . U . . .
H10I H 0.5729 0.9226 0.4853 0.068 Uiso 1 1 calc R U . . .
H10J H 0.5650 1.0630 0.5307 0.068 Uiso 1 1 calc R U . . .
C19A C 0.5392(5) 0.9316(4) 0.6601(4) 0.0361(9) Uani 1 1 d . U . . .
H19A H 0.5584 0.9970 0.7211 0.043 Uiso 1 1 calc R U . . .
C101 C 0.3902(5) 0.9044(4) 0.6516(4) 0.0403(10) Uani 1 1 d . U . . .
C102 C 0.3719(4) 0.7981(4) 0.7367(4) 0.0365(9) Uani 1 1 d . U . . .
H10K H 0.2876 0.7512 0.7207 0.044 Uiso 1 1 calc R U . . .
H10L H 0.3766 0.8295 0.8172 0.044 Uiso 1 1 calc R U . . .
C115 C 0.5246(6) 0.4274(4) 0.8948(4) 0.0532(13) Uani 1 1 d . U . . .
H11I H 0.4641 0.3549 0.8797 0.080 Uiso 1 1 calc R U . . .
H11J H 0.4949 0.4766 0.9585 0.080 Uiso 1 1 calc R U . . .
H11K H 0.6115 0.3990 0.9156 0.080 Uiso 1 1 calc R U . . .
C117 C 0.8233(7) 0.4039(9) 0.5403(6) 0.088(2) Uani 1 1 d . U . . .
H117 H 0.7655 0.4171 0.4753 0.106 Uiso 1 1 calc R U . . .
C118 C 0.9547(9) 0.4243(11) 0.5316(8) 0.112(3) Uani 1 1 d . U . . .
H118 H 0.9875 0.4518 0.4605 0.135 Uiso 1 1 calc R U . . .
C112 C 0.3181(6) 1.0190(5) 0.6860(5) 0.0565(13) Uani 1 1 d . U . . .
H11L H 0.3450 1.0431 0.7657 0.085 Uiso 1 1 calc R U . . .
H11M H 0.2242 0.9988 0.6801 0.085 Uiso 1 1 calc R U . . .
H11N H 0.3390 1.0884 0.6341 0.085 Uiso 1 1 calc R U . . .
C111 C 0.3349(6) 0.8626(5) 0.5302(5) 0.0607(14) Uani 1 1 d . U . . .
H11O H 0.3483 0.9308 0.4754 0.091 Uiso 1 1 calc R U . . .
H11P H 0.2416 0.8407 0.5329 0.091 Uiso 1 1 calc R U . . .
H11Q H 0.3796 0.7896 0.5054 0.091 Uiso 1 1 calc R U . . .
C122 C 1.1784(12) 0.4224(13) 0.6131(13) 0.123(3) Uani 1 1 d . U . . .
F101 F 1.2175(8) 0.5320(9) 0.5893(12) 0.196(4) Uani 1 1 d . U . . .
F103 F 1.2333(7) 0.3482(10) 0.5559(12) 0.221(5) Uani 1 1 d . U . . .
F102 F 1.2398(9) 0.4316(17) 0.7106(14) 0.260(6) Uani 1 1 d . 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
Br1 C6 1.987(7) . ?
Br1A C106 1.975(7) . ?
C22 F3 1.254(12) . ?
C22 F1 1.225(12) . ?
C22 F2 1.183(14) . ?
C22 C19 1.484(10) . ?
S1 O2 1.431(3) . ?
S1 O1 1.436(4) . ?
S1 C16 1.765(5) . ?
S1 N2 1.598(3) . ?
S101 O102 1.434(3) . ?
S101 O101 1.433(3) . ?
S101 N102 1.591(3) . ?
S101 C116 1.760(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C7 1.534(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.322(10) . ?
C18 C17 1.386(9) . ?
C19 C20 1.409(11) . ?
C20 H20 0.9500 . ?
C20 C21 1.363(10) . ?
C21 H21 0.9500 . ?
C21 C16 1.382(8) . ?
C16 C17 1.378(7) . ?
N2 C14 1.306(5) . ?
C14 N1 1.318(5) . ?
C14 C15 1.499(6) . ?
N1 H1 0.8800 . ?
N1 C3 1.460(5) . ?
C3 H3 1.0000 . ?
C3 C3A 1.540(6) . ?
C3 C2 1.525(6) . ?
C3A C10 1.526(6) . ?
C3A C4 1.530(6) . ?
C3A C9A 1.575(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C7 1.529(7) . ?
C7 C8 1.577(8) . ?
C7 C6 1.532(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.484(9) . ?
C6 H6 1.0000 . ?
C6 C5 1.538(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.518(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C17 H17 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.531(6) . ?
C1 C9A 1.538(7) . ?
C1 C11 1.528(6) . ?
C1 C12 1.540(7) . ?
C9A H9A 1.0000 . ?
C9A C9 1.526(6) . ?
C9 H9B 0.9900 . ?
C9 H9C 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C113 H11D 0.9800 . ?
C113 H11E 0.9800 . ?
C113 H11F 0.9800 . ?
C113 C107 1.531(8) . ?
C107 C110 1.531(7) . ?
C107 C106 1.532(10) . ?
C107 C108 1.556(9) . ?
C110 H11G 0.9900 . ?
C110 H11H 0.9900 . ?
C110 C13A 1.531(6) . ?
C13A C103 1.531(6) . ?
C13A C104 1.550(6) . ?
C13A C19A 1.560(6) . ?
C103 H103 1.0000 . ?
C103 N101 1.453(5) . ?
C103 C102 1.533(6) . ?
N101 H101 0.8800 . ?
N101 C114 1.317(5) . ?
C114 N102 1.317(5) . ?
C114 C115 1.495(6) . ?
C116 C121 1.340(8) . ?
C116 C117 1.364(9) . ?
C121 H121 0.9500 . ?
C121 C120 1.392(12) . ?
C120 H120 0.9500 . ?
C120 C119 1.358(14) . ?
C119 C118 1.367(13) . ?
C119 C122 1.456(14) . ?
C106 H106 1.0000 . ?
C106 C105 1.523(9) . ?
C105 H10C 0.9900 . ?
C105 H10D 0.9900 . ?
C105 C104 1.511(7) . ?
C104 H10E 0.9900 . ?
C104 H10F 0.9900 . ?
C108 H10G 0.9900 . ?
C108 H10H 0.9900 . ?
C108 C109 1.509(9) . ?
C109 H10I 0.9900 . ?
C109 H10J 0.9900 . ?
C109 C19A 1.528(6) . ?
C19A H19A 1.0000 . ?
C19A C101 1.547(7) . ?
C101 C102 1.519(6) . ?
C101 C112 1.534(6) . ?
C101 C111 1.546(7) . ?
C102 H10K 0.9900 . ?
C102 H10L 0.9900 . ?
C115 H11I 0.9800 . ?
C115 H11J 0.9800 . ?
C115 H11K 0.9800 . ?
C117 H117 0.9500 . ?
C117 C118 1.371(11) . ?
C118 H118 0.9500 . ?
C112 H11L 0.9800 . ?
C112 H11M 0.9800 . ?
C112 H11N 0.9800 . ?
C111 H11O 0.9800 . ?
C111 H11P 0.9800 . ?
C111 H11Q 0.9800 . ?
C122 F101 1.258(16) . ?
C122 F103 1.217(15) . ?
C122 F102 1.266(17) . ?

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
F3 C22 C19 113.7(8) . . ?
F1 C22 F3 102.9(12) . . ?
F1 C22 C19 114.8(8) . . ?
F2 C22 F3 104.0(12) . . ?
F2 C22 F1 103.5(12) . . ?
F2 C22 C19 116.3(10) . . ?
O2 S1 O1 116.6(2) . . ?
O2 S1 C16 106.7(2) . . ?
O2 S1 N2 115.6(2) . . ?
O1 S1 C16 106.3(2) . . ?
O1 S1 N2 106.60(19) . . ?
N2 S1 C16 103.94(19) . . ?
O102 S101 O101 116.3(2) . . ?
O102 S101 N102 116.42(19) . . ?
O102 S101 C116 106.5(2) . . ?
O101 S101 N102 107.04(19) . . ?
O101 S101 C116 106.5(2) . . ?
N102 S101 C116 102.7(2) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
C19 C18 H18 119.1 . . ?
C19 C18 C17 121.8(6) . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C22 120.5(7) . . ?
C18 C19 C20 119.1(6) . . ?
C20 C19 C22 120.4(7) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(6) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.8 . . ?
C20 C21 C16 118.4(6) . . ?
C16 C21 H21 120.8 . . ?
C21 C16 S1 119.6(4) . . ?
C21 C16 C17 120.9(5) . . ?
C17 C16 S1 119.4(4) . . ?
C14 N2 S1 123.1(3) . . ?
N2 C14 N1 118.4(3) . . ?
N2 C14 C15 127.4(4) . . ?
N1 C14 C15 114.2(4) . . ?
C14 N1 H1 117.1 . . ?
C14 N1 C3 125.9(3) . . ?
C3 N1 H1 117.1 . . ?
N1 C3 H3 108.7 . . ?
N1 C3 C3A 115.4(3) . . ?
N1 C3 C2 110.8(3) . . ?
C3A C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C2 C3 C3A 104.4(3) . . ?
C3 C3A C9A 103.1(3) . . ?
C10 C3A C3 112.2(3) . . ?
C10 C3A C4 108.2(4) . . ?
C10 C3A C9A 110.6(3) . . ?
C4 C3A C3 111.2(3) . . ?
C4 C3A C9A 111.6(3) . . ?
C3A C10 H10A 109.6 . . ?
C3A C10 H10B 109.6 . . ?
C3A C10 C7 110.2(4) . . ?
H10A C10 H10B 108.1 . . ?
C7 C10 H10A 109.6 . . ?
C7 C10 H10B 109.6 . . ?
C13 C7 C8 108.6(5) . . ?
C10 C7 C13 109.4(4) . . ?
C10 C7 C8 110.0(5) . . ?
C6 C7 C13 112.2(6) . . ?
C6 C7 C10 109.0(4) . . ?
C6 C7 C8 107.7(4) . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 113.0(4) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
Br1 C6 H6 107.9 . . ?
C7 C6 Br1 112.5(4) . . ?
C7 C6 H6 107.9 . . ?
C7 C6 C5 112.9(5) . . ?
C5 C6 Br1 107.6(4) . . ?
C5 C6 H6 107.9 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C4 C5 C6 111.6(4) . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C3A C4 H4A 109.1 . . ?
C3A C4 H4B 109.1 . . ?
C5 C4 C3A 112.5(4) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C18 C17 H17 120.6 . . ?
C16 C17 C18 118.7(6) . . ?
C16 C17 H17 120.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C3 C2 C1 103.5(3) . . ?
H2A C2 H2B 109.0 . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C2 C1 C9A 102.1(3) . . ?
C2 C1 C12 109.7(4) . . ?
C9A C1 C12 113.5(4) . . ?
C11 C1 C2 111.5(4) . . ?
C11 C1 C9A 111.5(4) . . ?
C11 C1 C12 108.5(4) . . ?
C3A C9A H9A 106.8 . . ?
C1 C9A C3A 108.0(3) . . ?
C1 C9A H9A 106.8 . . ?
C9 C9A C3A 111.8(4) . . ?
C9 C9A C1 116.3(4) . . ?
C9 C9A H9A 106.8 . . ?
C8 C9 C9A 113.0(4) . . ?
C8 C9 H9B 109.0 . . ?
C8 C9 H9C 109.0 . . ?
C9A C9 H9B 109.0 . . ?
C9A C9 H9C 109.0 . . ?
H9B C9 H9C 107.8 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H11D C113 H11E 109.5 . . ?
H11D C113 H11F 109.5 . . ?
H11E C113 H11F 109.5 . . ?
C107 C113 H11D 109.5 . . ?
C107 C113 H11E 109.5 . . ?
C107 C113 H11F 109.5 . . ?
C113 C107 C108 109.1(5) . . ?
C110 C107 C113 109.7(4) . . ?
C110 C107 C108 109.8(5) . . ?
C106 C107 C113 112.5(6) . . ?
C106 C107 C110 108.9(4) . . ?
C106 C107 C108 106.8(5) . . ?
C107 C110 H11G 109.5 . . ?
C107 C110 H11H 109.5 . . ?
C107 C110 C13A 110.9(4) . . ?
H11G C110 H11H 108.0 . . ?
C13A C110 H11G 109.5 . . ?
C13A C110 H11H 109.5 . . ?
C110 C13A C103 113.4(3) . . ?
C110 C13A C104 107.2(4) . . ?
C110 C13A C19A 110.7(3) . . ?
C103 C13A C104 111.0(3) . . ?
C103 C13A C19A 103.9(3) . . ?
C104 C13A C19A 110.6(3) . . ?
C13A C103 H103 108.3 . . ?
N101 C103 C13A 116.5(3) . . ?
N101 C103 H103 108.3 . . ?
N101 C103 C102 110.7(3) . . ?
C102 C103 C13A 104.3(3) . . ?
C102 C103 H103 108.3 . . ?
C103 N101 H101 117.0 . . ?
C114 N101 C103 126.0(3) . . ?
C114 N101 H101 117.0 . . ?
N101 C114 C115 114.2(4) . . ?
N102 C114 N101 118.7(3) . . ?
N102 C114 C115 127.2(4) . . ?
C114 N102 S101 124.5(3) . . ?
C121 C116 S101 119.2(5) . . ?
C121 C116 C117 120.1(6) . . ?
C117 C116 S101 120.7(4) . . ?
C116 C121 H121 120.0 . . ?
C116 C121 C120 120.0(7) . . ?
C120 C121 H121 120.0 . . ?
C121 C120 H120 119.8 . . ?
C119 C120 C121 120.4(8) . . ?
C119 C120 H120 119.8 . . ?
C120 C119 C118 118.9(7) . . ?
C120 C119 C122 120.9(10) . . ?
C118 C119 C122 120.1(10) . . ?
Br1A C106 H106 107.6 . . ?
C107 C106 Br1A 112.4(4) . . ?
C107 C106 H106 107.6 . . ?
C107 C106 C105 113.1(5) . . ?
C105 C106 Br1A 108.3(5) . . ?
C105 C106 H106 107.6 . . ?
C106 C105 H10C 109.1 . . ?
C106 C105 H10D 109.1 . . ?
H10C C105 H10D 107.8 . . ?
C104 C105 C106 112.7(5) . . ?
C104 C105 H10C 109.1 . . ?
C104 C105 H10D 109.1 . . ?
C13A C104 H10E 109.1 . . ?
C13A C104 H10F 109.1 . . ?
C105 C104 C13A 112.3(4) . . ?
C105 C104 H10E 109.1 . . ?
C105 C104 H10F 109.1 . . ?
H10E C104 H10F 107.9 . . ?
C107 C108 H10G 108.9 . . ?
C107 C108 H10H 108.9 . . ?
H10G C108 H10H 107.7 . . ?
C109 C108 C107 113.4(4) . . ?
C109 C108 H10G 108.9 . . ?
C109 C108 H10H 108.9 . . ?
C108 C109 H10I 109.4 . . ?
C108 C109 H10J 109.4 . . ?
C108 C109 C19A 111.2(5) . . ?
H10I C109 H10J 108.0 . . ?
C19A C109 H10I 109.4 . . ?
C19A C109 H10J 109.4 . . ?
C13A C19A H19A 107.1 . . ?
C109 C19A C13A 112.0(4) . . ?
C109 C19A H19A 107.1 . . ?
C109 C19A C101 115.8(4) . . ?
C101 C19A C13A 107.3(3) . . ?
C101 C19A H19A 107.1 . . ?
C19A C101 C111 114.1(4) . . ?
C102 C101 C19A 102.6(3) . . ?
C102 C101 C112 111.6(4) . . ?
C102 C101 C111 109.8(4) . . ?
C112 C101 C19A 111.4(4) . . ?
C112 C101 C111 107.4(4) . . ?
C103 C102 H10K 111.2 . . ?
C103 C102 H10L 111.2 . . ?
C101 C102 C103 103.0(3) . . ?
C101 C102 H10K 111.2 . . ?
C101 C102 H10L 111.2 . . ?
H10K C102 H10L 109.1 . . ?
C114 C115 H11I 109.5 . . ?
C114 C115 H11J 109.5 . . ?
C114 C115 H11K 109.5 . . ?
H11I C115 H11J 109.5 . . ?
H11I C115 H11K 109.5 . . ?
H11J C115 H11K 109.5 . . ?
C116 C117 H117 119.9 . . ?
C116 C117 C118 120.1(7) . . ?
C118 C117 H117 119.9 . . ?
C119 C118 C117 120.5(8) . . ?
C119 C118 H118 119.8 . . ?
C117 C118 H118 119.8 . . ?
C101 C112 H11L 109.5 . . ?
C101 C112 H11M 109.5 . . ?
C101 C112 H11N 109.5 . . ?
H11L C112 H11M 109.5 . . ?
H11L C112 H11N 109.5 . . ?
H11M C112 H11N 109.5 . . ?
C101 C111 H11O 109.5 . . ?
C101 C111 H11P 109.5 . . ?
C101 C111 H11Q 109.5 . . ?
H11O C111 H11P 109.5 . . ?
H11O C111 H11Q 109.5 . . ?
H11P C111 H11Q 109.5 . . ?
F101 C122 C119 114.7(11) . . ?
F101 C122 F103 109.8(14) . . ?
F101 C122 F102 90.0(12) . . ?
F103 C122 C119 119.4(11) . . ?
F103 C122 F102 107.3(14) . . ?
F102 C122 C119 111.7(13) . . ?

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
Br1 C6 C5 C4 -74.6(5) . . . . ?
Br1A C106 C105 C104 -75.4(6) . . . . ?
C22 C19 C20 C21 -179.4(7) . . . . ?
S1 C16 C17 C18 -178.7(5) . . . . ?
S1 N2 C14 N1 176.5(3) . . . . ?
S1 N2 C14 C15 -4.7(7) . . . . ?
S101 C116 C121 C120 179.0(7) . . . . ?
S101 C116 C117 C118 -179.5(8) . . . . ?
F3 C22 C19 C18 110.0(12) . . . . ?
F3 C22 C19 C20 -70.8(13) . . . . ?
C13 C7 C8 C9 120.3(6) . . . . ?
C13 C7 C6 Br1 -53.7(5) . . . . ?
C13 C7 C6 C5 -175.7(5) . . . . ?
F1 C22 C19 C18 -131.8(12) . . . . ?
F1 C22 C19 C20 47.3(14) . . . . ?
F2 C22 C19 C18 -10.8(16) . . . . ?
F2 C22 C19 C20 168.3(14) . . . . ?
O2 S1 C16 C21 162.3(5) . . . . ?
O2 S1 C16 C17 -19.6(5) . . . . ?
O2 S1 N2 C14 26.0(4) . . . . ?
O1 S1 C16 C21 37.2(5) . . . . ?
O1 S1 C16 C17 -144.7(4) . . . . ?
O1 S1 N2 C14 157.4(4) . . . . ?
O102 S101 N102 C114 11.1(5) . . . . ?
O102 S101 C116 C121 -29.0(6) . . . . ?
O102 S101 C116 C117 151.1(6) . . . . ?
O101 S101 N102 C114 143.2(4) . . . . ?
O101 S101 C116 C121 -153.8(5) . . . . ?
O101 S101 C116 C117 26.3(6) . . . . ?
C18 C19 C20 C21 -0.3(12) . . . . ?
C19 C18 C17 C16 -0.1(11) . . . . ?
C19 C20 C21 C16 -0.3(12) . . . . ?
C20 C21 C16 S1 178.9(6) . . . . ?
C20 C21 C16 C17 0.8(10) . . . . ?
C21 C16 C17 C18 -0.6(9) . . . . ?
C16 S1 N2 C14 -90.5(4) . . . . ?
N2 S1 C16 C21 -75.1(5) . . . . ?
N2 S1 C16 C17 103.0(5) . . . . ?
N2 C14 N1 C3 2.0(6) . . . . ?
C14 N1 C3 C3A -99.3(4) . . . . ?
C14 N1 C3 C2 142.4(4) . . . . ?
N1 C3 C3A C10 91.5(4) . . . . ?
N1 C3 C3A C4 -29.8(5) . . . . ?
N1 C3 C3A C9A -149.5(3) . . . . ?
N1 C3 C2 C1 168.4(3) . . . . ?
C3 C3A C10 C7 174.1(4) . . . . ?
C3 C3A C4 C5 -178.2(4) . . . . ?
C3 C3A C9A C1 2.5(4) . . . . ?
C3 C3A C9A C9 -126.7(4) . . . . ?
C3 C2 C1 C9A -40.6(4) . . . . ?
C3 C2 C1 C11 -159.7(4) . . . . ?
C3 C2 C1 C12 80.0(4) . . . . ?
C3A C3 C2 C1 43.5(4) . . . . ?
C3A C10 C7 C13 -175.8(5) . . . . ?
C3A C10 C7 C8 -56.6(5) . . . . ?
C3A C10 C7 C6 61.2(6) . . . . ?
C3A C9A C9 C8 -49.5(5) . . . . ?
C10 C3A C4 C5 58.1(5) . . . . ?
C10 C3A C9A C1 122.5(4) . . . . ?
C10 C3A C9A C9 -6.6(5) . . . . ?
C10 C7 C8 C9 0.6(6) . . . . ?
C10 C7 C6 Br1 67.7(5) . . . . ?
C10 C7 C6 C5 -54.4(6) . . . . ?
C7 C8 C9 C9A 52.9(6) . . . . ?
C7 C6 C5 C4 50.1(7) . . . . ?
C8 C7 C6 Br1 -173.0(3) . . . . ?
C8 C7 C6 C5 64.9(5) . . . . ?
C6 C7 C8 C9 -118.0(5) . . . . ?
C6 C5 C4 C3A -51.9(6) . . . . ?
C4 C3A C10 C7 -62.8(5) . . . . ?
C4 C3A C9A C1 -117.0(4) . . . . ?
C4 C3A C9A C9 113.9(4) . . . . ?
C17 C18 C19 C22 179.6(7) . . . . ?
C17 C18 C19 C20 0.5(12) . . . . ?
C15 C14 N1 C3 -176.9(4) . . . . ?
C2 C3 C3A C10 -146.6(4) . . . . ?
C2 C3 C3A C4 92.0(4) . . . . ?
C2 C3 C3A C9A -27.7(4) . . . . ?
C2 C1 C9A C3A 23.3(4) . . . . ?
C2 C1 C9A C9 149.8(4) . . . . ?
C1 C9A C9 C8 -174.2(4) . . . . ?
C9A C3A C10 C7 59.7(5) . . . . ?
C9A C3A C4 C5 -63.7(5) . . . . ?
C11 C1 C9A C3A 142.4(4) . . . . ?
C11 C1 C9A C9 -91.0(5) . . . . ?
C12 C1 C9A C3A -94.7(4) . . . . ?
C12 C1 C9A C9 31.9(5) . . . . ?
C113 C107 C110 C13A -175.4(5) . . . . ?
C113 C107 C106 Br1A -52.3(6) . . . . ?
C113 C107 C106 C105 -175.3(5) . . . . ?
C113 C107 C108 C109 119.5(6) . . . . ?
C107 C110 C13A C103 174.5(4) . . . . ?
C107 C110 C13A C104 -62.6(5) . . . . ?
C107 C110 C13A C19A 58.2(5) . . . . ?
C107 C106 C105 C104 49.9(7) . . . . ?
C107 C108 C109 C19A 54.4(6) . . . . ?
C110 C107 C106 Br1A 69.5(5) . . . . ?
C110 C107 C106 C105 -53.5(6) . . . . ?
C110 C107 C108 C109 -0.7(7) . . . . ?
C110 C13A C103 N101 90.1(4) . . . . ?
C110 C13A C103 C102 -147.6(4) . . . . ?
C110 C13A C104 C105 57.4(5) . . . . ?
C110 C13A C19A C109 -3.8(5) . . . . ?
C110 C13A C19A C101 124.3(4) . . . . ?
C13A C103 N101 C114 -99.7(5) . . . . ?
C13A C103 C102 C101 43.0(4) . . . . ?
C13A C19A C101 C102 23.7(4) . . . . ?
C13A C19A C101 C112 143.2(4) . . . . ?
C13A C19A C101 C111 -95.0(4) . . . . ?
C103 C13A C104 C105 -178.2(4) . . . . ?
C103 C13A C19A C109 -125.9(4) . . . . ?
C103 C13A C19A C101 2.2(4) . . . . ?
C103 N101 C114 N102 5.1(6) . . . . ?
C103 N101 C114 C115 -175.0(4) . . . . ?
N101 C103 C102 C101 169.1(3) . . . . ?
N101 C114 N102 S101 176.5(3) . . . . ?
N102 S101 C116 C121 93.8(6) . . . . ?
N102 S101 C116 C117 -86.0(6) . . . . ?
C116 S101 N102 C114 -104.8(4) . . . . ?
C116 C121 C120 C119 0.8(15) . . . . ?
C116 C117 C118 C119 0.2(16) . . . . ?
C121 C116 C117 C118 0.7(13) . . . . ?
C121 C120 C119 C118 0.0(15) . . . . ?
C121 C120 C119 C122 -178.1(10) . . . . ?
C120 C119 C118 C117 -0.5(15) . . . . ?
C120 C119 C122 F101 -118.7(14) . . . . ?
C120 C119 C122 F103 108.0(16) . . . . ?
C120 C119 C122 F102 -18.1(18) . . . . ?
C106 C107 C110 C13A 61.1(6) . . . . ?
C106 C107 C108 C109 -118.7(5) . . . . ?
C106 C105 C104 C13A -51.9(7) . . . . ?
C104 C13A C103 N101 -30.7(5) . . . . ?
C104 C13A C103 C102 91.7(4) . . . . ?
C104 C13A C19A C109 114.9(4) . . . . ?
C104 C13A C19A C101 -117.0(4) . . . . ?
C108 C107 C110 C13A -55.6(6) . . . . ?
C108 C107 C106 Br1A -171.9(3) . . . . ?
C108 C107 C106 C105 65.1(6) . . . . ?
C108 C109 C19A C13A -51.5(6) . . . . ?
C108 C109 C19A C101 -174.9(4) . . . . ?
C109 C19A C101 C102 149.6(4) . . . . ?
C109 C19A C101 C112 -90.9(5) . . . . ?
C109 C19A C101 C111 30.9(5) . . . . ?
C19A C13A C103 N101 -149.6(3) . . . . ?
C19A C13A C103 C102 -27.3(4) . . . . ?
C19A C13A C104 C105 -63.4(5) . . . . ?
C19A C101 C102 C103 -40.5(4) . . . . ?
C102 C103 N101 C114 141.4(4) . . . . ?
C115 C114 N102 S101 -3.3(7) . . . . ?
C117 C116 C121 C120 -1.1(13) . . . . ?
C118 C119 C122 F101 63.2(16) . . . . ?
C118 C119 C122 F103 -70.1(18) . . . . ?
C118 C119 C122 F102 163.8(14) . . . . ?
C112 C101 C102 C103 -159.9(4) . . . . ?
C111 C101 C102 C103 81.1(5) . . . . ?
C122 C119 C118 C117 177.6(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_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_5a
_database_code_depnum_ccdc_archive 'CCDC 2430947'
loop_
_audit_author_name
_audit_author_address
'Borodina Tatiana'
;Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Science
Russia
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2025-02-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
"N-(9-iodo-4,4,8-trimethyltricyclo[6.3.1.0^2,5]dodecan-1-yl)-N'- (methylsulfonyl)acetimidamide"
_chemical_formula_moiety         'C18 H31 I N2 O2 S'
_chemical_formula_sum            'C18 H31 I N2 O2 S'
_chemical_formula_weight         466.41
_chemical_absolute_configuration .
_chemical_melting_point          437.6
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2188(10)
_cell_length_b                   15.8711(18)
_cell_length_c                   18.129(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.025(5)
_cell_angle_gamma                90
_cell_volume                     2056.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9175
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.885
_shelx_estimated_absorpt_T_min   0.434
_exptl_absorpt_coefficient_mu    1.671
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1656 before and 0.0859 after correction.
The Ratio of minimum to maximum transmission is 0.7124.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.075
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1484
_diffrn_reflns_av_unetI/netI     0.2944
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42760
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.816
_diffrn_reflns_theta_min         2.269
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                5447
_reflns_number_total             8548
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (BRUKER, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.32B (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.584
_refine_diff_density_min         -1.110
_refine_diff_density_rms         0.165
_refine_ls_abs_structure_details 
;
 Flack x determined using 1818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.011(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         8548
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1004
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of
0.05 and sigma for terminal atoms of 0.1
Uanis(O1) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(O101) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C18) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C9(H9), C102(H102), C2(H2), C5(H5), C105(H105), C109(H109)
3.b Secondary CH2 refined with riding coordinates:
 C112(H11C,H11D), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C10(H10A,H10B),
 C11(H11A,H11B), C12(H12A,H12B), C103(H10C,H10D), C106(H10E,H10F), C107(H10G,
 H10H), C110(H11N,H11O), C111(H11P,H11Q)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N101(H101)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C114(H11E,H11F,H11G), C118(H11H,H11I,H11J), C113(H11K,H11L,H11M),
 C115(H11R,H11S,H11T), C117(H11U,H11V,H11W), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.025
;
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 0.97291(9) 0.38062(3) 0.44625(4) 0.0733(2) Uani 1 1 d . . . . .
I101 I 1.00404(10) 0.61866(4) -0.01862(4) 0.0715(2) Uani 1 1 d . . . . .
S1 S 0.1931(3) 0.05597(18) 0.34272(11) 0.0564(6) Uani 1 1 d . . . . .
S101 S 0.2182(3) 0.31412(17) -0.14939(11) 0.0532(6) Uani 1 1 d . . . . .
N2 N 0.3804(7) 0.0860(4) 0.3929(3) 0.0402(15) Uani 1 1 d . . . . .
N102 N 0.4075(7) 0.3350(4) -0.0961(3) 0.0399(15) Uani 1 1 d . . . . .
O102 O 0.0862(7) 0.2839(5) -0.1040(4) 0.075(2) Uani 1 1 d . . . . .
C9 C 0.8332(9) 0.3286(5) 0.5366(4) 0.0432(18) Uani 1 1 d . . . . .
H9 H 0.8374 0.3724 0.5764 0.052 Uiso 1 1 calc R U . . .
C102 C 0.6260(9) 0.3523(4) 0.0701(3) 0.0305(15) Uani 1 1 d . . . . .
H102 H 0.5617 0.3980 0.0948 0.037 Uiso 1 1 calc R U . . .
O101 O 0.2362(9) 0.2670(7) -0.2127(4) 0.123(3) Uani 1 1 d . U . . .
C112 C 0.9226(8) 0.4112(4) 0.0341(3) 0.0314(15) Uani 1 1 d . . . . .
H11C H 0.9822 0.4312 -0.0087 0.038 Uiso 1 1 calc R U . . .
H11D H 0.9848 0.3579 0.0517 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6052(12) -0.0575(5) 0.6631(4) 0.055(2) Uani 1 1 d . . . . .
H13A H 0.4885 -0.0861 0.6699 0.083 Uiso 1 1 calc R U . . .
H13B H 0.6917 -0.0593 0.7098 0.083 Uiso 1 1 calc R U . . .
H13C H 0.6621 -0.0859 0.6238 0.083 Uiso 1 1 calc R U . . .
C4 C 0.5640(9) 0.0330(5) 0.6412(3) 0.0353(16) Uani 1 1 d . . . . .
C3 C 0.4705(10) 0.0484(5) 0.5595(3) 0.0378(17) Uani 1 1 d . . . . .
H3A H 0.4937 0.0030 0.5245 0.045 Uiso 1 1 calc R U . . .
H3B H 0.3358 0.0624 0.5549 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5986(8) 0.1255(4) 0.5572(3) 0.0280(14) Uani 1 1 d . . . . .
H2 H 0.5366 0.1747 0.5780 0.034 Uiso 1 1 calc R U . . .
C1 C 0.6895(8) 0.1567(5) 0.4900(3) 0.0273(14) Uani 1 1 d . . . . .
N1 N 0.6913(7) 0.0892(4) 0.4344(3) 0.0302(13) Uani 1 1 d . . . . .
H1 H 0.8022 0.0683 0.4300 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5486(9) 0.0554(5) 0.3898(3) 0.0341(16) Uani 1 1 d . . . . .
O2 O 0.0619(8) 0.0354(5) 0.3913(4) 0.072(2) Uani 1 1 d . U . . .
O1 O 0.2120(10) -0.0036(8) 0.2884(5) 0.146(4) Uani 1 1 d . U . . .
C5 C 0.7313(9) 0.0851(5) 0.6208(4) 0.0343(16) Uani 1 1 d . . . . .
H5 H 0.8161 0.0458 0.5982 0.041 Uiso 1 1 calc R U . . .
C6 C 0.8539(11) 0.1437(5) 0.6748(4) 0.0436(19) Uani 1 1 d . . . . .
H6A H 0.8072 0.1432 0.7236 0.052 Uiso 1 1 calc R U . . .
H6B H 0.9836 0.1219 0.6824 0.052 Uiso 1 1 calc R U . . .
C7 C 0.8552(10) 0.2342(5) 0.6465(4) 0.0428(18) Uani 1 1 d . . . . .
H7A H 0.9309 0.2684 0.6853 0.051 Uiso 1 1 calc R U . . .
H7B H 0.7254 0.2558 0.6416 0.051 Uiso 1 1 calc R U . . .
C8 C 0.9309(9) 0.2503(5) 0.5709(4) 0.0382(17) Uani 1 1 d . . . . .
C10 C 0.6308(9) 0.3131(5) 0.5064(4) 0.0412(17) Uani 1 1 d . . . . .
H10A H 0.5808 0.3637 0.4785 0.049 Uiso 1 1 calc R U . . .
H10B H 0.5597 0.3058 0.5489 0.049 Uiso 1 1 calc R U . . .
C11 C 0.5963(9) 0.2368(5) 0.4557(4) 0.0370(16) Uani 1 1 d . . . . .
H11A H 0.6445 0.2488 0.4082 0.044 Uiso 1 1 calc R U . . .
H11B H 0.4599 0.2272 0.4441 0.044 Uiso 1 1 calc R U . . .
C12 C 0.8948(8) 0.1769(4) 0.5149(4) 0.0313(15) Uani 1 1 d . . . . .
H12A H 0.9539 0.1907 0.4703 0.038 Uiso 1 1 calc R U . . .
H12B H 0.9570 0.1258 0.5378 0.038 Uiso 1 1 calc R U . . .
C15 C 1.1424(10) 0.2606(6) 0.5897(5) 0.059(2) Uani 1 1 d . . . . .
H15A H 1.1980 0.2649 0.5435 0.089 Uiso 1 1 calc R U . . .
H15B H 1.1949 0.2117 0.6183 0.089 Uiso 1 1 calc R U . . .
H15C H 1.1703 0.3119 0.6193 0.089 Uiso 1 1 calc R U . . .
C14 C 0.4551(10) 0.0756(6) 0.6983(4) 0.051(2) Uani 1 1 d . . . . .
H14A H 0.3376 0.0452 0.7002 0.077 Uiso 1 1 calc R U . . .
H14B H 0.4277 0.1341 0.6834 0.077 Uiso 1 1 calc R U . . .
H14C H 0.5306 0.0745 0.7476 0.077 Uiso 1 1 calc R U . . .
C17 C 0.5982(11) -0.0150(6) 0.3405(5) 0.056(2) Uani 1 1 d . . . . .
H17A H 0.5344 -0.0667 0.3524 0.084 Uiso 1 1 calc R U . . .
H17B H 0.7338 -0.0240 0.3488 0.084 Uiso 1 1 calc R U . . .
H17C H 0.5587 0.0000 0.2882 0.084 Uiso 1 1 calc R U . . .
C114 C 0.4772(12) 0.2863(6) 0.2027(5) 0.066(3) Uani 1 1 d . . . . .
H11E H 0.5427 0.2746 0.2527 0.099 Uiso 1 1 calc R U . . .
H11F H 0.3527 0.2605 0.1971 0.099 Uiso 1 1 calc R U . . .
H11G H 0.4648 0.3474 0.1956 0.099 Uiso 1 1 calc R U . . .
C104 C 0.5878(10) 0.2499(5) 0.1450(4) 0.0405(17) Uani 1 1 d . . . . .
C105 C 0.7576(9) 0.3060(5) 0.1308(4) 0.0381(17) Uani 1 1 d . . . . .
H105 H 0.8430 0.2701 0.1052 0.046 Uiso 1 1 calc R U . . .
C101 C 0.7160(8) 0.3924(5) 0.0064(3) 0.0287(15) Uani 1 1 d . . . . .
N101 N 0.7196(7) 0.3340(4) -0.0562(3) 0.0335(14) Uani 1 1 d . . . . .
H101 H 0.8299 0.3139 -0.0626 0.040 Uiso 1 1 calc R U . . .
C116 C 0.5751(9) 0.3080(5) -0.1044(3) 0.0363(17) Uani 1 1 d . . . . .
C118 C 0.1427(16) 0.4153(8) -0.1757(6) 0.092(4) Uani 1 1 d . . . . .
H11H H 0.1470 0.4509 -0.1314 0.139 Uiso 1 1 calc R U . . .
H11I H 0.0141 0.4128 -0.2015 0.139 Uiso 1 1 calc R U . . .
H11J H 0.2245 0.4391 -0.2092 0.139 Uiso 1 1 calc R U . . .
C113 C 0.6241(13) 0.1566(6) 0.1598(5) 0.066(2) Uani 1 1 d . . . . .
H11K H 0.6935 0.1491 0.2098 0.098 Uiso 1 1 calc R U . . .
H11L H 0.6976 0.1339 0.1228 0.098 Uiso 1 1 calc R U . . .
H11M H 0.5045 0.1266 0.1562 0.098 Uiso 1 1 calc R U . . .
C103 C 0.4999(10) 0.2741(5) 0.0650(4) 0.0440(18) Uani 1 1 d . . . . .
H10C H 0.5259 0.2332 0.0265 0.053 Uiso 1 1 calc R U . . .
H10D H 0.3647 0.2873 0.0603 0.053 Uiso 1 1 calc R U . . .
C106 C 0.8792(12) 0.3584(6) 0.1890(4) 0.056(2) Uani 1 1 d . . . . .
H10E H 1.0092 0.3371 0.1941 0.067 Uiso 1 1 calc R U . . .
H10F H 0.8338 0.3515 0.2377 0.067 Uiso 1 1 calc R U . . .
C107 C 0.8787(12) 0.4523(6) 0.1693(4) 0.048(2) Uani 1 1 d . . . . .
H10G H 0.9512 0.4827 0.2115 0.058 Uiso 1 1 calc R U . . .
H10H H 0.7481 0.4728 0.1649 0.058 Uiso 1 1 calc R U . . .
C108 C 0.9590(10) 0.4767(5) 0.0968(4) 0.0383(17) Uani 1 1 d . . . . .
C109 C 0.8634(10) 0.5585(5) 0.0689(4) 0.0437(18) Uani 1 1 d . . . . .
H109 H 0.8697 0.5984 0.1119 0.052 Uiso 1 1 calc R U . . .
C110 C 0.6601(10) 0.5469(5) 0.0371(4) 0.0437(18) Uani 1 1 d . . . . .
H11N H 0.6127 0.6005 0.0137 0.052 Uiso 1 1 calc R U . . .
H11O H 0.5881 0.5351 0.0786 0.052 Uiso 1 1 calc R U . . .
C111 C 0.6223(9) 0.4763(5) -0.0206(4) 0.0371(17) Uani 1 1 d . . . . .
H11P H 0.6692 0.4939 -0.0671 0.045 Uiso 1 1 calc R U . . .
H11Q H 0.4856 0.4676 -0.0323 0.045 Uiso 1 1 calc R U . . .
C115 C 1.1703(10) 0.4853(6) 0.1165(5) 0.060(2) Uani 1 1 d . . . . .
H11R H 1.2205 0.4353 0.1440 0.089 Uiso 1 1 calc R U . . .
H11S H 1.1992 0.5355 0.1474 0.089 Uiso 1 1 calc R U . . .
H11T H 1.2270 0.4907 0.0706 0.089 Uiso 1 1 calc R U . . .
C117 C 0.6242(11) 0.2487(7) -0.1636(5) 0.069(3) Uani 1 1 d . . . . .
H11U H 0.5551 0.1959 -0.1613 0.103 Uiso 1 1 calc R U . . .
H11V H 0.7589 0.2372 -0.1552 0.103 Uiso 1 1 calc R U . . .
H11W H 0.5906 0.2746 -0.2127 0.103 Uiso 1 1 calc R U . . .
C18 C 0.1134(19) 0.1487(11) 0.3000(8) 0.137(6) Uani 1 1 d . U . . .
H18A H 0.1343 0.1952 0.3358 0.206 Uiso 1 1 calc R U . . .
H18B H -0.0206 0.1438 0.2820 0.206 Uiso 1 1 calc R U . . .
H18C H 0.1813 0.1599 0.2578 0.206 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 C9 2.200(6) . ?
I101 C109 2.215(7) . ?
S1 N2 1.593(6) . ?
S1 O2 1.419(6) . ?
S1 O1 1.386(8) . ?
S1 C18 1.724(16) . ?
S101 N102 1.595(6) . ?
S101 O102 1.426(6) . ?
S101 O101 1.392(7) . ?
S101 C118 1.741(12) . ?
N2 C16 1.316(9) . ?
N102 C116 1.312(8) . ?
C9 H9 1.0000 . ?
C9 C8 1.520(11) . ?
C9 C10 1.507(10) . ?
C102 H102 1.0000 . ?
C102 C105 1.537(9) . ?
C102 C101 1.539(9) . ?
C102 C103 1.534(10) . ?
C112 H11C 0.9900 . ?
C112 H11D 0.9900 . ?
C112 C101 1.535(9) . ?
C112 C108 1.536(10) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C4 1.509(11) . ?
C4 C3 1.559(9) . ?
C4 C5 1.551(9) . ?
C4 C14 1.540(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.537(9) . ?
C2 H2 1.0000 . ?
C2 C1 1.543(8) . ?
C2 C5 1.533(9) . ?
C1 N1 1.473(9) . ?
C1 C11 1.530(9) . ?
C1 C12 1.522(9) . ?
N1 H1 0.8800 . ?
N1 C16 1.330(8) . ?
C16 C17 1.505(10) . ?
C5 H5 1.0000 . ?
C5 C6 1.538(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.525(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.566(10) . ?
C8 C12 1.543(10) . ?
C8 C15 1.526(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.520(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C114 H11E 0.9800 . ?
C114 H11F 0.9800 . ?
C114 H11G 0.9800 . ?
C114 C104 1.516(10) . ?
C104 C105 1.564(10) . ?
C104 C113 1.522(11) . ?
C104 C103 1.548(10) . ?
C105 H105 1.0000 . ?
C105 C106 1.522(11) . ?
C101 N101 1.470(8) . ?
C101 C111 1.543(10) . ?
N101 H101 0.8800 . ?
N101 C116 1.329(8) . ?
C116 C117 1.506(10) . ?
C118 H11H 0.9800 . ?
C118 H11I 0.9800 . ?
C118 H11J 0.9800 . ?
C113 H11K 0.9800 . ?
C113 H11L 0.9800 . ?
C113 H11M 0.9800 . ?
C103 H10C 0.9900 . ?
C103 H10D 0.9900 . ?
C106 H10E 0.9900 . ?
C106 H10F 0.9900 . ?
C106 C107 1.531(13) . ?
C107 H10G 0.9900 . ?
C107 H10H 0.9900 . ?
C107 C108 1.558(10) . ?
C108 C109 1.524(11) . ?
C108 C115 1.523(10) . ?
C109 H109 1.0000 . ?
C109 C110 1.511(10) . ?
C110 H11N 0.9900 . ?
C110 H11O 0.9900 . ?
C110 C111 1.531(11) . ?
C111 H11P 0.9900 . ?
C111 H11Q 0.9900 . ?
C115 H11R 0.9800 . ?
C115 H11S 0.9800 . ?
C115 H11T 0.9800 . ?
C117 H11U 0.9800 . ?
C117 H11V 0.9800 . ?
C117 H11W 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 S1 C18 101.8(5) . . ?
O2 S1 N2 107.5(4) . . ?
O2 S1 C18 105.4(6) . . ?
O1 S1 N2 116.7(4) . . ?
O1 S1 O2 115.2(6) . . ?
O1 S1 C18 108.8(7) . . ?
N102 S101 C118 100.6(5) . . ?
O102 S101 N102 107.8(4) . . ?
O102 S101 C118 105.1(5) . . ?
O101 S101 N102 116.1(4) . . ?
O101 S101 O102 116.2(6) . . ?
O101 S101 C118 109.4(6) . . ?
C16 N2 S1 125.5(5) . . ?
C116 N102 S101 126.0(5) . . ?
I1 C9 H9 107.8 . . ?
C8 C9 I1 112.2(4) . . ?
C8 C9 H9 107.8 . . ?
C10 C9 I1 108.3(5) . . ?
C10 C9 H9 107.8 . . ?
C10 C9 C8 112.7(6) . . ?
C105 C102 H102 107.8 . . ?
C105 C102 C101 116.8(5) . . ?
C101 C102 H102 107.8 . . ?
C103 C102 H102 107.8 . . ?
C103 C102 C105 87.6(5) . . ?
C103 C102 C101 126.7(5) . . ?
H11C C112 H11D 107.5 . . ?
C101 C112 H11C 108.4 . . ?
C101 C112 H11D 108.4 . . ?
C101 C112 C108 115.6(5) . . ?
C108 C112 H11C 108.4 . . ?
C108 C112 H11D 108.4 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
C13 C4 C3 116.3(6) . . ?
C13 C4 C5 116.0(6) . . ?
C13 C4 C14 109.9(6) . . ?
C5 C4 C3 86.4(5) . . ?
C14 C4 C3 112.1(6) . . ?
C14 C4 C5 114.5(6) . . ?
C4 C3 H3A 114.0 . . ?
C4 C3 H3B 114.0 . . ?
H3A C3 H3B 111.2 . . ?
C2 C3 C4 88.2(5) . . ?
C2 C3 H3A 114.0 . . ?
C2 C3 H3B 114.0 . . ?
C3 C2 H2 108.0 . . ?
C3 C2 C1 126.9(5) . . ?
C1 C2 H2 108.0 . . ?
C5 C2 C3 87.8(5) . . ?
C5 C2 H2 108.0 . . ?
C5 C2 C1 115.9(5) . . ?
N1 C1 C2 110.6(6) . . ?
N1 C1 C11 111.8(5) . . ?
N1 C1 C12 104.8(5) . . ?
C11 C1 C2 112.1(5) . . ?
C12 C1 C2 109.7(5) . . ?
C12 C1 C11 107.4(6) . . ?
C1 N1 H1 115.5 . . ?
C16 N1 C1 128.9(5) . . ?
C16 N1 H1 115.5 . . ?
N2 C16 N1 117.9(6) . . ?
N2 C16 C17 126.6(6) . . ?
N1 C16 C17 115.6(6) . . ?
C4 C5 H5 107.9 . . ?
C2 C5 C4 88.6(5) . . ?
C2 C5 H5 107.9 . . ?
C2 C5 C6 118.0(6) . . ?
C6 C5 C4 124.6(6) . . ?
C6 C5 H5 107.9 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.7(6) . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C6 C7 H7A 107.9 . . ?
C6 C7 H7B 107.9 . . ?
C6 C7 C8 117.8(6) . . ?
H7A C7 H7B 107.2 . . ?
C8 C7 H7A 107.9 . . ?
C8 C7 H7B 107.9 . . ?
C9 C8 C7 107.0(6) . . ?
C9 C8 C12 108.8(6) . . ?
C9 C8 C15 113.4(7) . . ?
C12 C8 C7 113.9(6) . . ?
C15 C8 C7 106.5(6) . . ?
C15 C8 C12 107.4(6) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C9 C10 C11 114.7(6) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C1 C11 H11A 109.0 . . ?
C1 C11 H11B 109.0 . . ?
C10 C11 C1 112.9(6) . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C1 C12 C8 115.0(5) . . ?
C1 C12 H12A 108.5 . . ?
C1 C12 H12B 108.5 . . ?
C8 C12 H12A 108.5 . . ?
C8 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H11E C114 H11F 109.5 . . ?
H11E C114 H11G 109.5 . . ?
H11F C114 H11G 109.5 . . ?
C104 C114 H11E 109.5 . . ?
C104 C114 H11F 109.5 . . ?
C104 C114 H11G 109.5 . . ?
C114 C104 C105 113.4(7) . . ?
C114 C104 C113 110.1(6) . . ?
C114 C104 C103 111.4(6) . . ?
C113 C104 C105 117.6(7) . . ?
C113 C104 C103 116.4(7) . . ?
C103 C104 C105 86.2(5) . . ?
C102 C105 C104 88.3(5) . . ?
C102 C105 H105 107.4 . . ?
C104 C105 H105 107.4 . . ?
C106 C105 C102 118.3(7) . . ?
C106 C105 C104 125.9(6) . . ?
C106 C105 H105 107.4 . . ?
C102 C101 C111 112.6(5) . . ?
C112 C101 C102 109.2(5) . . ?
C112 C101 C111 107.4(6) . . ?
N101 C101 C102 111.9(6) . . ?
N101 C101 C112 104.7(5) . . ?
N101 C101 C111 110.7(5) . . ?
C101 N101 H101 116.3 . . ?
C116 N101 C101 127.3(5) . . ?
C116 N101 H101 116.3 . . ?
N102 C116 N101 118.4(6) . . ?
N102 C116 C117 126.8(6) . . ?
N101 C116 C117 114.8(6) . . ?
S101 C118 H11H 109.5 . . ?
S101 C118 H11I 109.5 . . ?
S101 C118 H11J 109.5 . . ?
H11H C118 H11I 109.5 . . ?
H11H C118 H11J 109.5 . . ?
H11I C118 H11J 109.5 . . ?
C104 C113 H11K 109.5 . . ?
C104 C113 H11L 109.5 . . ?
C104 C113 H11M 109.5 . . ?
H11K C113 H11L 109.5 . . ?
H11K C113 H11M 109.5 . . ?
H11L C113 H11M 109.5 . . ?
C102 C103 C104 88.9(5) . . ?
C102 C103 H10C 113.8 . . ?
C102 C103 H10D 113.8 . . ?
C104 C103 H10C 113.8 . . ?
C104 C103 H10D 113.8 . . ?
H10C C103 H10D 111.0 . . ?
C105 C106 H10E 109.0 . . ?
C105 C106 H10F 109.0 . . ?
C105 C106 C107 112.9(7) . . ?
H10E C106 H10F 107.8 . . ?
C107 C106 H10E 109.0 . . ?
C107 C106 H10F 109.0 . . ?
C106 C107 H10G 108.1 . . ?
C106 C107 H10H 108.1 . . ?
C106 C107 C108 116.7(7) . . ?
H10G C107 H10H 107.3 . . ?
C108 C107 H10G 108.1 . . ?
C108 C107 H10H 108.1 . . ?
C112 C108 C107 114.3(6) . . ?
C109 C108 C112 107.9(6) . . ?
C109 C108 C107 106.7(6) . . ?
C115 C108 C112 107.2(6) . . ?
C115 C108 C107 107.7(6) . . ?
C115 C108 C109 113.2(7) . . ?
I101 C109 H109 108.1 . . ?
C108 C109 I101 111.9(4) . . ?
C108 C109 H109 108.1 . . ?
C110 C109 I101 107.3(5) . . ?
C110 C109 C108 113.2(6) . . ?
C110 C109 H109 108.1 . . ?
C109 C110 H11N 108.5 . . ?
C109 C110 H11O 108.5 . . ?
C109 C110 C111 114.9(6) . . ?
H11N C110 H11O 107.5 . . ?
C111 C110 H11N 108.5 . . ?
C111 C110 H11O 108.5 . . ?
C101 C111 H11P 109.0 . . ?
C101 C111 H11Q 109.0 . . ?
C110 C111 C101 112.7(5) . . ?
C110 C111 H11P 109.1 . . ?
C110 C111 H11Q 109.1 . . ?
H11P C111 H11Q 107.8 . . ?
C108 C115 H11R 109.5 . . ?
C108 C115 H11S 109.5 . . ?
C108 C115 H11T 109.5 . . ?
H11R C115 H11S 109.5 . . ?
H11R C115 H11T 109.5 . . ?
H11S C115 H11T 109.5 . . ?
C116 C117 H11U 109.5 . . ?
C116 C117 H11V 109.5 . . ?
C116 C117 H11W 109.5 . . ?
H11U C117 H11V 109.5 . . ?
H11U C117 H11W 109.5 . . ?
H11V C117 H11W 109.5 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C9 C8 C7 164.8(4) . . . . ?
I1 C9 C8 C12 -71.7(6) . . . . ?
I1 C9 C8 C15 47.7(7) . . . . ?
I1 C9 C10 C11 74.6(6) . . . . ?
I101 C109 C110 C111 73.7(7) . . . . ?
S1 N2 C16 N1 178.2(5) . . . . ?
S1 N2 C16 C17 -1.8(11) . . . . ?
S101 N102 C116 N101 177.6(6) . . . . ?
S101 N102 C116 C117 -3.0(13) . . . . ?
O102 S101 N102 C116 128.4(7) . . . . ?
C9 C8 C12 C1 -57.4(7) . . . . ?
C9 C10 C11 C1 51.3(8) . . . . ?
C102 C105 C106 C107 -10.9(9) . . . . ?
C102 C101 N101 C116 71.3(9) . . . . ?
C102 C101 C111 C110 69.1(7) . . . . ?
O101 S101 N102 C116 -4.0(10) . . . . ?
C112 C101 N101 C116 -170.6(7) . . . . ?
C112 C101 C111 C110 -51.1(7) . . . . ?
C112 C108 C109 I101 -69.7(6) . . . . ?
C112 C108 C109 C110 51.7(7) . . . . ?
C13 C4 C3 C2 -139.5(6) . . . . ?
C13 C4 C5 C2 139.8(6) . . . . ?
C13 C4 C5 C6 -96.5(8) . . . . ?
C4 C3 C2 C1 143.6(6) . . . . ?
C4 C3 C2 C5 22.4(5) . . . . ?
C4 C5 C6 C7 -122.2(7) . . . . ?
C3 C4 C5 C2 22.2(5) . . . . ?
C3 C4 C5 C6 145.9(7) . . . . ?
C3 C2 C1 N1 -18.7(9) . . . . ?
C3 C2 C1 C11 106.8(8) . . . . ?
C3 C2 C1 C12 -133.8(7) . . . . ?
C3 C2 C5 C4 -22.5(5) . . . . ?
C3 C2 C5 C6 -151.7(6) . . . . ?
C2 C1 N1 C16 69.8(8) . . . . ?
C2 C1 C11 C10 68.1(7) . . . . ?
C2 C1 C12 C8 -64.4(7) . . . . ?
C2 C5 C6 C7 -12.6(9) . . . . ?
C1 C2 C5 C4 -153.0(6) . . . . ?
C1 C2 C5 C6 77.8(7) . . . . ?
C1 N1 C16 N2 1.7(10) . . . . ?
C1 N1 C16 C17 -178.2(7) . . . . ?
N1 C1 C11 C10 -166.9(5) . . . . ?
N1 C1 C12 C8 176.7(6) . . . . ?
O2 S1 N2 C16 126.9(7) . . . . ?
O1 S1 N2 C16 -4.3(10) . . . . ?
C5 C4 C3 C2 -22.1(5) . . . . ?
C5 C2 C1 N1 89.5(7) . . . . ?
C5 C2 C1 C11 -145.0(6) . . . . ?
C5 C2 C1 C12 -25.6(8) . . . . ?
C5 C6 C7 C8 -60.8(9) . . . . ?
C6 C7 C8 C9 152.1(7) . . . . ?
C6 C7 C8 C12 31.8(9) . . . . ?
C6 C7 C8 C15 -86.4(8) . . . . ?
C7 C8 C12 C1 61.9(8) . . . . ?
C8 C9 C10 C11 -50.1(8) . . . . ?
C10 C9 C8 C7 -72.7(7) . . . . ?
C10 C9 C8 C12 50.8(7) . . . . ?
C10 C9 C8 C15 170.2(6) . . . . ?
C11 C1 N1 C16 -55.9(9) . . . . ?
C11 C1 C12 C8 57.7(7) . . . . ?
C12 C1 N1 C16 -172.0(6) . . . . ?
C12 C1 C11 C10 -52.5(7) . . . . ?
C15 C8 C12 C1 179.5(6) . . . . ?
C14 C4 C3 C2 92.9(6) . . . . ?
C14 C4 C5 C2 -90.5(6) . . . . ?
C14 C4 C5 C6 33.2(10) . . . . ?
C114 C104 C105 C102 -89.5(7) . . . . ?
C114 C104 C105 C106 34.8(11) . . . . ?
C114 C104 C103 C102 91.4(7) . . . . ?
C104 C105 C106 C107 -121.2(8) . . . . ?
C105 C102 C101 C112 -24.9(8) . . . . ?
C105 C102 C101 N101 90.5(7) . . . . ?
C105 C102 C101 C111 -144.1(6) . . . . ?
C105 C102 C103 C104 22.6(5) . . . . ?
C105 C104 C103 C102 -22.3(5) . . . . ?
C105 C106 C107 C108 -62.8(9) . . . . ?
C101 C102 C105 C104 -153.0(6) . . . . ?
C101 C102 C105 C106 76.5(8) . . . . ?
C101 C102 C103 C104 144.9(7) . . . . ?
C101 C112 C108 C107 60.1(8) . . . . ?
C101 C112 C108 C109 -58.4(8) . . . . ?
C101 C112 C108 C115 179.4(6) . . . . ?
C101 N101 C116 N102 -1.4(11) . . . . ?
C101 N101 C116 C117 179.1(7) . . . . ?
N101 C101 C111 C110 -164.8(5) . . . . ?
C118 S101 N102 C116 -121.9(8) . . . . ?
C113 C104 C105 C102 140.1(7) . . . . ?
C113 C104 C105 C106 -95.6(9) . . . . ?
C113 C104 C103 C102 -141.3(7) . . . . ?
C103 C102 C105 C104 -22.4(5) . . . . ?
C103 C102 C105 C106 -153.0(6) . . . . ?
C103 C102 C101 C112 -133.6(7) . . . . ?
C103 C102 C101 N101 -18.2(9) . . . . ?
C103 C102 C101 C111 107.3(8) . . . . ?
C103 C104 C105 C102 22.2(5) . . . . ?
C103 C104 C105 C106 146.5(8) . . . . ?
C106 C107 C108 C112 33.9(9) . . . . ?
C106 C107 C108 C109 153.1(7) . . . . ?
C106 C107 C108 C115 -85.1(9) . . . . ?
C107 C108 C109 I101 167.0(5) . . . . ?
C107 C108 C109 C110 -71.6(7) . . . . ?
C108 C112 C101 C102 -64.2(8) . . . . ?
C108 C112 C101 N101 175.8(6) . . . . ?
C108 C112 C101 C111 58.1(7) . . . . ?
C108 C109 C110 C111 -50.3(8) . . . . ?
C109 C110 C111 C101 50.0(8) . . . . ?
C111 C101 N101 C116 -55.2(9) . . . . ?
C115 C108 C109 I101 48.7(7) . . . . ?
C115 C108 C109 C110 170.1(6) . . . . ?
C18 S1 N2 C16 -122.6(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ?hloroform-dietil ether'
