# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

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

data_mo_Astakhova_A61_0m
_database_code_depnum_ccdc_archive 'CCDC 2159125'
loop_
_audit_author_name
_audit_author_address
'Irina Sterkhova'
;Irkutsk Institute of Chemistry, Siberian Branch of Russian Academy of Science
Russia
;
_audit_update_record             
;
2022-03-16 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
N-(3-(bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)-N'-((trifluoromethyl)sulfonyl)acetamidamide
_chemical_name_common            ?
_chemical_melting_point          428
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 Br F3 N2 O2 S'
_chemical_formula_weight         405.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

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

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

_cell_length_a                   10.233(4)
_cell_length_b                   12.379(4)
_cell_length_c                   13.802(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.009(13)
_cell_angle_gamma                90
_cell_volume                     1688.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    125
_cell_measurement_theta_min      5
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.594
_shelx_estimated_absorpt_T_min   0.423
_shelx_estimated_absorpt_T_max   0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4649
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   IuS
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60138
_diffrn_reflns_av_unetI/netI     0.1276
_diffrn_reflns_av_R_equivalents  0.2297
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         30.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5035
_reflns_number_gt                2579
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1339P)²+1.6510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5035
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1864
_refine_ls_R_factor_gt           0.0929
_refine_ls_wR_factor_ref         0.2728
_refine_ls_wR_factor_gt          0.2417
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.23031(10) 0.99208(6) 0.97539(7) 0.0796(4) Uani 1 1 d . . . . .
S1 S 0.51515(12) 0.62455(10) 1.23828(8) 0.0331(3) Uani 1 1 d . . . . .
F1 F 0.3318(4) 0.4734(3) 1.2216(4) 0.0780(12) Uani 1 1 d . . . . .
F2 F 0.4806(5) 0.4410(4) 1.1416(3) 0.0874(14) Uani 1 1 d . . . . .
F3 F 0.5314(5) 0.4253(4) 1.3007(4) 0.0948(15) Uani 1 1 d . . . . .
O1 O 0.6563(4) 0.6198(4) 1.2465(3) 0.0612(12) Uani 1 1 d . . . . .
O2 O 0.4732(4) 0.6618(3) 1.3232(3) 0.0523(10) Uani 1 1 d . . . . .
N1 N 0.3544(4) 0.7311(3) 0.9813(3) 0.0343(9) Uani 1 1 d . . . . .
H17 H 0.3744 0.7524 0.9260 0.041 Uiso 1 1 calc R U . . .
N2 N 0.4178(4) 0.6721(4) 1.1398(3) 0.0341(9) Uani 1 1 d . . . . .
C1 C 0.1773(6) 0.6566(6) 0.7664(4) 0.0554(16) Uani 1 1 d . . . . .
H4 H 0.1397 0.5993 0.7183 0.083 Uiso 1 1 calc R U . . .
H5 H 0.2516 0.6274 0.8197 0.083 Uiso 1 1 calc R U . . .
H1 H 0.2115 0.7151 0.7319 0.083 Uiso 1 1 calc R U . . .
C2 C 0.0661(5) 0.7008(5) 0.8125(4) 0.0425(13) Uani 1 1 d . . . . .
C3 C 0.1123(5) 0.7877(4) 0.8963(3) 0.0337(11) Uani 1 1 d . . . . .
C4 C 0.2112(5) 0.7241(4) 0.9820(3) 0.0347(11) Uani 1 1 d . . . . .
H2 H 0.2022 0.7532 1.0475 0.042 Uiso 1 1 calc R U . . .
C5 C 0.4539(5) 0.7069(4) 1.0599(3) 0.0321(10) Uani 1 1 d . . . . .
C6 C 0.4622(7) 0.4828(5) 1.2255(5) 0.0512(15) Uani 1 1 d . . . . .
C7 C 0.1535(6) 0.6085(5) 0.9698(5) 0.0519(15) Uani 1 1 d . . . . .
H3 H 0.1328 0.5833 1.0323 0.062 Uiso 1 1 calc R U . . .
H16 H 0.2178 0.5574 0.9516 0.062 Uiso 1 1 calc R U . . .
C8 C 0.0227(6) 0.6191(5) 0.8836(5) 0.0520(15) Uani 1 1 d . . . . .
H15 H -0.0139 0.5492 0.8514 0.062 Uiso 1 1 calc R U . . .
C9 C -0.0775(6) 0.6849(6) 0.9257(5) 0.0604(17) Uani 1 1 d . . . . .
H13 H -0.0817 0.6573 0.9922 0.072 Uiso 1 1 calc R U . . .
H14 H -0.1694 0.6832 0.8795 0.072 Uiso 1 1 calc R U . . .
C10 C -0.0168(5) 0.8005(5) 0.9341(4) 0.0476(14) Uani 1 1 d . . . . .
H12 H -0.0809 0.8520 0.8916 0.057 Uiso 1 1 calc R U . . .
H11 H 0.0059 0.8263 1.0044 0.057 Uiso 1 1 calc R U . . .
C11 C -0.0513(7) 0.7383(8) 0.7250(5) 0.071(2) Uani 1 1 d . . . . .
H6 H -0.0182 0.7922 0.6850 0.107 Uiso 1 1 calc R U . . .
H7 H -0.1225 0.7703 0.7515 0.107 Uiso 1 1 calc R U . . .
H8 H -0.0880 0.6762 0.6826 0.107 Uiso 1 1 calc R U . . .
C12 C 0.1634(6) 0.8912(4) 0.8632(4) 0.0441(12) Uani 1 1 d . . . . .
H10 H 0.0895 0.9262 0.8122 0.053 Uiso 1 1 calc R U . . .
H9 H 0.2375 0.8749 0.8314 0.053 Uiso 1 1 calc R U . . .
C13 C 0.5964(5) 0.7240(5) 1.0504(4) 0.0475(14) Uani 1 1 d . . . . .
H20 H 0.5933 0.7481 0.9822 0.071 Uiso 1 1 calc R U . . .
H19 H 0.6469 0.6560 1.0643 0.071 Uiso 1 1 calc R U . . .
H18 H 0.6415 0.7791 1.0986 0.071 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 C12 1.969(6) . ?
S1 O1 1.421(4) . ?
S1 O2 1.425(4) . ?
S1 N2 1.576(4) . ?
S1 C6 1.832(6) . ?
F1 C6 1.327(8) . ?
F2 C6 1.325(7) . ?
F3 C6 1.306(7) . ?
N1 C5 1.316(6) . ?
N1 C4 1.470(6) . ?
N1 H17 0.8800 . ?
N2 C5 1.323(6) . ?
C1 C2 1.541(7) . ?
C1 H4 0.9800 . ?
C1 H5 0.9800 . ?
C1 H1 0.9800 . ?
C2 C11 1.538(8) . ?
C2 C8 1.553(8) . ?
C2 C3 1.561(7) . ?
C3 C12 1.500(7) . ?
C3 C10 1.549(7) . ?
C3 C4 1.556(6) . ?
C4 C7 1.541(8) . ?
C4 H2 1.0000 . ?
C5 C13 1.513(7) . ?
C7 C8 1.548(8) . ?
C7 H3 0.9900 . ?
C7 H16 0.9900 . ?
C8 C9 1.536(9) . ?
C8 H15 1.0000 . ?
C9 C10 1.553(9) . ?
C9 H13 0.9900 . ?
C9 H14 0.9900 . ?
C10 H12 0.9900 . ?
C10 H11 0.9900 . ?
C11 H6 0.9800 . ?
C11 H7 0.9800 . ?
C11 H8 0.9800 . ?
C12 H10 0.9900 . ?
C12 H9 0.9900 . ?
C13 H20 0.9800 . ?
C13 H19 0.9800 . ?
C13 H18 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 117.7(3) . . ?
O1 S1 N2 119.1(2) . . ?
O2 S1 N2 109.3(2) . . ?
O1 S1 C6 103.7(3) . . ?
O2 S1 C6 104.2(3) . . ?
N2 S1 C6 99.8(3) . . ?
C5 N1 C4 122.7(4) . . ?
C5 N1 H17 118.6 . . ?
C4 N1 H17 118.6 . . ?
C5 N2 S1 126.2(3) . . ?
C2 C1 H4 109.5 . . ?
C2 C1 H5 109.5 . . ?
H4 C1 H5 109.5 . . ?
C2 C1 H1 109.5 . . ?
H4 C1 H1 109.5 . . ?
H5 C1 H1 109.5 . . ?
C11 C2 C1 107.0(5) . . ?
C11 C2 C8 113.6(5) . . ?
C1 C2 C8 113.1(5) . . ?
C11 C2 C3 113.6(5) . . ?
C1 C2 C3 115.9(4) . . ?
C8 C2 C3 93.5(4) . . ?
C12 C3 C10 114.2(4) . . ?
C12 C3 C4 117.0(4) . . ?
C10 C3 C4 103.9(4) . . ?
C12 C3 C2 115.2(4) . . ?
C10 C3 C2 101.5(4) . . ?
C4 C3 C2 103.2(4) . . ?
N1 C4 C7 114.1(4) . . ?
N1 C4 C3 114.8(4) . . ?
C7 C4 C3 103.4(4) . . ?
N1 C4 H2 108.1 . . ?
C7 C4 H2 108.1 . . ?
C3 C4 H2 108.1 . . ?
N1 C5 N2 116.0(4) . . ?
N1 C5 C13 117.0(4) . . ?
N2 C5 C13 127.0(4) . . ?
F3 C6 F2 108.2(5) . . ?
F3 C6 F1 108.5(6) . . ?
F2 C6 F1 107.4(5) . . ?
F3 C6 S1 111.1(4) . . ?
F2 C6 S1 110.7(5) . . ?
F1 C6 S1 110.9(4) . . ?
C4 C7 C8 103.6(4) . . ?
C4 C7 H3 111.0 . . ?
C8 C7 H3 111.0 . . ?
C4 C7 H16 111.0 . . ?
C8 C7 H16 111.0 . . ?
H3 C7 H16 109.0 . . ?
C9 C8 C7 106.5(5) . . ?
C9 C8 C2 102.8(5) . . ?
C7 C8 C2 102.1(4) . . ?
C9 C8 H15 114.7 . . ?
C7 C8 H15 114.7 . . ?
C2 C8 H15 114.7 . . ?
C8 C9 C10 102.9(4) . . ?
C8 C9 H13 111.2 . . ?
C10 C9 H13 111.2 . . ?
C8 C9 H14 111.2 . . ?
C10 C9 H14 111.2 . . ?
H13 C9 H14 109.1 . . ?
C3 C10 C9 103.9(4) . . ?
C3 C10 H12 111.0 . . ?
C9 C10 H12 111.0 . . ?
C3 C10 H11 111.0 . . ?
C9 C10 H11 111.0 . . ?
H12 C10 H11 109.0 . . ?
C2 C11 H6 109.5 . . ?
C2 C11 H7 109.5 . . ?
H6 C11 H7 109.5 . . ?
C2 C11 H8 109.5 . . ?
H6 C11 H8 109.5 . . ?
H7 C11 H8 109.5 . . ?
C3 C12 Br1 112.3(3) . . ?
C3 C12 H10 109.1 . . ?
Br1 C12 H10 109.1 . . ?
C3 C12 H9 109.1 . . ?
Br1 C12 H9 109.1 . . ?
H10 C12 H9 107.9 . . ?
C5 C13 H20 109.5 . . ?
C5 C13 H19 109.5 . . ?
H20 C13 H19 109.5 . . ?
C5 C13 H18 109.5 . . ?
H20 C13 H18 109.5 . . ?
H19 C13 H18 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
O1 S1 N2 C5 1.9(6) . . . . ?
O2 S1 N2 C5 141.2(4) . . . . ?
C6 S1 N2 C5 -109.9(5) . . . . ?
C11 C2 C3 C12 -60.8(6) . . . . ?
C1 C2 C3 C12 63.7(6) . . . . ?
C8 C2 C3 C12 -178.5(4) . . . . ?
C11 C2 C3 C10 63.0(6) . . . . ?
C1 C2 C3 C10 -172.5(5) . . . . ?
C8 C2 C3 C10 -54.6(4) . . . . ?
C11 C2 C3 C4 170.5(5) . . . . ?
C1 C2 C3 C4 -65.0(6) . . . . ?
C8 C2 C3 C4 52.8(4) . . . . ?
C5 N1 C4 C7 -78.7(6) . . . . ?
C5 N1 C4 C3 162.2(4) . . . . ?
C12 C3 C4 N1 -34.2(6) . . . . ?
C10 C3 C4 N1 -161.0(4) . . . . ?
C2 C3 C4 N1 93.4(5) . . . . ?
C12 C3 C4 C7 -159.1(4) . . . . ?
C10 C3 C4 C7 74.0(5) . . . . ?
C2 C3 C4 C7 -31.6(5) . . . . ?
C4 N1 C5 N2 2.1(7) . . . . ?
C4 N1 C5 C13 -176.6(5) . . . . ?
S1 N2 C5 N1 172.0(4) . . . . ?
S1 N2 C5 C13 -9.5(8) . . . . ?
O1 S1 C6 F3 56.4(5) . . . . ?
O2 S1 C6 F3 -67.3(5) . . . . ?
N2 S1 C6 F3 179.8(5) . . . . ?
O1 S1 C6 F2 -63.8(5) . . . . ?
O2 S1 C6 F2 172.5(4) . . . . ?
N2 S1 C6 F2 59.6(5) . . . . ?
O1 S1 C6 F1 177.1(4) . . . . ?
O2 S1 C6 F1 53.4(5) . . . . ?
N2 S1 C6 F1 -59.5(5) . . . . ?
N1 C4 C7 C8 -129.0(4) . . . . ?
C3 C4 C7 C8 -3.7(5) . . . . ?
C4 C7 C8 C9 -69.6(6) . . . . ?
C4 C7 C8 C2 37.9(6) . . . . ?
C11 C2 C8 C9 -62.4(6) . . . . ?
C1 C2 C8 C9 175.3(4) . . . . ?
C3 C2 C8 C9 55.2(5) . . . . ?
C11 C2 C8 C7 -172.7(5) . . . . ?
C1 C2 C8 C7 65.1(6) . . . . ?
C3 C2 C8 C7 -55.0(5) . . . . ?
C7 C8 C9 C10 71.8(6) . . . . ?
C2 C8 C9 C10 -35.1(5) . . . . ?
C12 C3 C10 C9 159.8(4) . . . . ?
C4 C3 C10 C9 -71.5(5) . . . . ?
C2 C3 C10 C9 35.3(5) . . . . ?
C8 C9 C10 C3 -0.4(6) . . . . ?
C10 C3 C12 Br1 66.8(5) . . . . ?
C4 C3 C12 Br1 -54.9(5) . . . . ?
C2 C3 C12 Br1 -176.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H20 O2 0.98 2.48 3.373(6) 150.5 4_575
C12 H9 O2 0.99 2.49 3.419(7) 157.1 4_575
N1 H17 O2 0.88 2.22 3.062(6) 161.1 4_575
C13 H20 O2 0.98 2.48 3.373(6) 150.5 4_575
C12 H9 O2 0.99 2.49 3.419(7) 157.1 4_575
N1 H17 O2 0.88 2.22 3.062(6) 161.1 4_575
C13 H20 O2 0.98 2.48 3.373(6) 150.5 4_575
C12 H9 O2 0.99 2.49 3.419(7) 157.1 4_575
N1 H17 O2 0.88 2.22 3.062(6) 161.1 4_575
N1 H17 O2 0.88 2.22 3.062(6) 161.1 4_575
C12 H9 O2 0.99 2.49 3.419(7) 157.1 4_575
C13 H20 O2 0.98 2.48 3.373(6) 150.5 4_575
N1 H17 O2 0.88 2.22 3.062(6) 161.1 4_575
C12 H9 O2 0.99 2.49 3.419(7) 157.1 4_575
C13 H20 O2 0.98 2.48 3.373(6) 150.5 4_575
N1 H17 O2 0.88 2.22 3.062(6) 161.1 4_575
C12 H9 O2 0.99 2.49 3.419(7) 157.1 4_575
C13 H20 O2 0.98 2.48 3.373(6) 150.5 4_575

_refine_diff_density_max         1.185
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.153

_shelxl_version_number           2013-3


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

data_mo_Garagan_102RA_0m
_database_code_depnum_ccdc_archive 'CCDC 2177406'
loop_
_audit_author_name
_audit_author_address
'Irina Sterkhova'
;Irkutsk Institute of Chemistry Siberian Branch of Russian Academy of Science
Russia
;
_audit_update_record             
;
2022-06-07 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N-(1-(bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)methanesulfonamide
_chemical_name_common            ?
_chemical_melting_point          378,5
_chemical_formula_moiety         'C11 H20 Br N O2 S'
_chemical_formula_sum            'C11 H20 Br N O2 S'
_chemical_formula_weight         310.25

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.546(4)
_cell_length_b                   8.634(4)
_cell_length_c                   10.975(5)
_cell_angle_alpha                75.459(14)
_cell_angle_beta                 80.375(16)
_cell_angle_gamma                83.214(15)
_cell_volume                     680.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    190
_cell_measurement_theta_min      5
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.163
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3260
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   IuS
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20988
_diffrn_reflns_av_unetI/netI     0.1370
_diffrn_reflns_av_R_equivalents  0.1604
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.445
_diffrn_reflns_theta_max         30.211
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3982
_reflns_number_gt                2207
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²+1.1921P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3982
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1647
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.1989
_refine_ls_wR_factor_gt          0.1720
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.24464(9) 0.36350(7) 0.39279(6) 0.0616(3) Uani 1 1 d . . . . .
S1 S 0.71735(16) 0.56450(17) 0.08579(12) 0.0404(3) Uani 1 1 d . . . . .
O1 O 0.7116(5) 0.5567(6) -0.0431(4) 0.0604(12) Uani 1 1 d . . . . .
O2 O 0.8460(5) 0.6601(6) 0.1071(4) 0.0644(13) Uani 1 1 d . . . . .
N1 N 0.5190(5) 0.6319(5) 0.1401(4) 0.0386(10) Uani 1 1 d . . . . .
H4 H 0.4308 0.6359 0.0986 0.046 Uiso 1 1 calc R U . . .
C1 C 0.7573(12) 0.3656(9) 0.1723(8) 0.087(3) Uani 1 1 d . . . . .
H1 H 0.8684 0.3190 0.1348 0.131 Uiso 1 1 calc R U . . .
H3 H 0.6601 0.3043 0.1704 0.131 Uiso 1 1 calc R U . . .
H20 H 0.7653 0.3650 0.2588 0.131 Uiso 1 1 calc R U . . .
C2 C 0.4862(6) 0.6862(6) 0.2585(4) 0.0334(10) Uani 1 1 d . . . . .
H19 H 0.5503 0.6106 0.3224 0.040 Uiso 1 1 calc R U . . .
C3 C 0.2833(6) 0.7062(5) 0.3131(4) 0.0289(9) Uani 1 1 d . . . . .
C4 C 0.2826(7) 0.7185(7) 0.4523(5) 0.0438(13) Uani 1 1 d . . . . .
H9 H 0.1630 0.7074 0.5008 0.053 Uiso 1 1 calc R U . . .
H10 H 0.3665 0.6369 0.4946 0.053 Uiso 1 1 calc R U . . .
C5 C 0.3429(9) 0.8889(8) 0.4358(7) 0.0663(19) Uani 1 1 d . . . . .
H2 H 0.2495 0.9553 0.4753 0.080 Uiso 1 1 calc R U . . .
H11 H 0.4526 0.8842 0.4723 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2232(7) 0.8842(6) 0.2469(5) 0.0449(13) Uani 1 1 d . . . . .
C7 C 0.0335(8) 0.9423(8) 0.3014(8) 0.0682(19) Uani 1 1 d . . . . .
H6 H 0.0240 1.0572 0.2865 0.102 Uiso 1 1 calc R U . . .
H7 H 0.0121 0.8961 0.3913 0.102 Uiso 1 1 calc R U . . .
H5 H -0.0542 0.9101 0.2607 0.102 Uiso 1 1 calc R U . . .
C8 C 0.3750(8) 0.9528(7) 0.2913(7) 0.0573(17) Uani 1 1 d . . . . .
H8 H 0.3775 1.0697 0.2631 0.069 Uiso 1 1 calc R U . . .
C9 C 0.5459(7) 0.8580(7) 0.2411(7) 0.0552(16) Uani 1 1 d . . . . .
H12 H 0.6428 0.8555 0.2897 0.066 Uiso 1 1 calc R U . . .
H13 H 0.5861 0.9053 0.1522 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2295(10) 0.9175(9) 0.1021(6) 0.072(2) Uani 1 1 d . . . . .
H14 H 0.1432 0.8571 0.0830 0.108 Uiso 1 1 calc R U . . .
H16 H 0.3481 0.8863 0.0642 0.108 Uiso 1 1 calc R U . . .
H15 H 0.2012 1.0300 0.0686 0.108 Uiso 1 1 calc R U . . .
C11 C 0.1639(6) 0.5816(6) 0.3045(5) 0.0356(11) Uani 1 1 d . . . . .
H18 H 0.1629 0.5844 0.2157 0.043 Uiso 1 1 calc R U . . .
H17 H 0.0415 0.6082 0.3414 0.043 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 C11 1.966(5) . ?
S1 O2 1.428(4) . ?
S1 O1 1.441(4) . ?
S1 N1 1.613(4) . ?
S1 C1 1.759(7) . ?
N1 C2 1.463(6) . ?
N1 H4 0.8600 . ?
C1 H1 0.9600 . ?
C1 H3 0.9600 . ?
C1 H20 0.9600 . ?
C2 C3 1.554(6) . ?
C2 C9 1.557(7) . ?
C2 H19 0.9800 . ?
C3 C11 1.512(6) . ?
C3 C4 1.557(6) . ?
C3 C6 1.575(7) . ?
C4 C5 1.550(8) . ?
C4 H9 0.9700 . ?
C4 H10 0.9700 . ?
C5 C8 1.531(10) . ?
C5 H2 0.9700 . ?
C5 H11 0.9700 . ?
C6 C7 1.534(8) . ?
C6 C10 1.536(9) . ?
C6 C8 1.547(8) . ?
C7 H6 0.9600 . ?
C7 H7 0.9600 . ?
C7 H5 0.9600 . ?
C8 C9 1.542(8) . ?
C8 H8 0.9800 . ?
C9 H12 0.9700 . ?
C9 H13 0.9700 . ?
C10 H14 0.9600 . ?
C10 H16 0.9600 . ?
C10 H15 0.9600 . ?
C11 H18 0.9700 . ?
C11 H17 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.1(3) . . ?
O2 S1 N1 108.1(2) . . ?
O1 S1 N1 106.9(2) . . ?
O2 S1 C1 108.8(4) . . ?
O1 S1 C1 106.5(4) . . ?
N1 S1 C1 108.2(3) . . ?
C2 N1 S1 121.4(3) . . ?
C2 N1 H4 119.3 . . ?
S1 N1 H4 119.3 . . ?
S1 C1 H1 109.5 . . ?
S1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
S1 C1 H20 109.5 . . ?
H1 C1 H20 109.5 . . ?
H3 C1 H20 109.5 . . ?
N1 C2 C3 113.8(4) . . ?
N1 C2 C9 112.8(4) . . ?
C3 C2 C9 101.9(4) . . ?
N1 C2 H19 109.3 . . ?
C3 C2 H19 109.3 . . ?
C9 C2 H19 109.3 . . ?
C11 C3 C2 117.5(4) . . ?
C11 C3 C4 112.7(4) . . ?
C2 C3 C4 104.7(4) . . ?
C11 C3 C6 115.0(4) . . ?
C2 C3 C6 103.6(4) . . ?
C4 C3 C6 101.6(4) . . ?
C5 C4 C3 103.4(5) . . ?
C5 C4 H9 111.1 . . ?
C3 C4 H9 111.1 . . ?
C5 C4 H10 111.1 . . ?
C3 C4 H10 111.1 . . ?
H9 C4 H10 109.0 . . ?
C8 C5 C4 103.2(4) . . ?
C8 C5 H2 111.1 . . ?
C4 C5 H2 111.1 . . ?
C8 C5 H11 111.1 . . ?
C4 C5 H11 111.1 . . ?
H2 C5 H11 109.1 . . ?
C7 C6 C10 107.1(5) . . ?
C7 C6 C8 113.2(5) . . ?
C10 C6 C8 115.1(5) . . ?
C7 C6 C3 113.6(4) . . ?
C10 C6 C3 114.9(5) . . ?
C8 C6 C3 92.8(4) . . ?
C6 C7 H6 109.5 . . ?
C6 C7 H7 109.5 . . ?
H6 C7 H7 109.5 . . ?
C6 C7 H5 109.5 . . ?
H6 C7 H5 109.5 . . ?
H7 C7 H5 109.5 . . ?
C5 C8 C9 106.8(6) . . ?
C5 C8 C6 102.9(4) . . ?
C9 C8 C6 102.6(4) . . ?
C5 C8 H8 114.4 . . ?
C9 C8 H8 114.4 . . ?
C6 C8 H8 114.4 . . ?
C8 C9 C2 104.3(4) . . ?
C8 C9 H12 110.9 . . ?
C2 C9 H12 110.9 . . ?
C8 C9 H13 110.9 . . ?
C2 C9 H13 110.9 . . ?
H12 C9 H13 108.9 . . ?
C6 C10 H14 109.5 . . ?
C6 C10 H16 109.5 . . ?
H14 C10 H16 109.5 . . ?
C6 C10 H15 109.5 . . ?
H14 C10 H15 109.5 . . ?
H16 C10 H15 109.5 . . ?
C3 C11 Br1 112.4(3) . . ?
C3 C11 H18 109.1 . . ?
Br1 C11 H18 109.1 . . ?
C3 C11 H17 109.1 . . ?
Br1 C11 H17 109.1 . . ?
H18 C11 H17 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
O2 S1 N1 C2 -39.1(5) . . . . ?
O1 S1 N1 C2 -167.2(4) . . . . ?
C1 S1 N1 C2 78.5(5) . . . . ?
S1 N1 C2 C3 -165.5(3) . . . . ?
S1 N1 C2 C9 79.0(5) . . . . ?
N1 C2 C3 C11 39.4(6) . . . . ?
C9 C2 C3 C11 161.2(4) . . . . ?
N1 C2 C3 C4 165.3(4) . . . . ?
C9 C2 C3 C4 -73.0(5) . . . . ?
N1 C2 C3 C6 -88.6(5) . . . . ?
C9 C2 C3 C6 33.2(5) . . . . ?
C11 C3 C4 C5 -157.8(4) . . . . ?
C2 C3 C4 C5 73.5(5) . . . . ?
C6 C3 C4 C5 -34.1(5) . . . . ?
C3 C4 C5 C8 -1.2(6) . . . . ?
C11 C3 C6 C7 59.6(6) . . . . ?
C2 C3 C6 C7 -170.8(5) . . . . ?
C4 C3 C6 C7 -62.4(6) . . . . ?
C11 C3 C6 C10 -64.1(6) . . . . ?
C2 C3 C6 C10 65.4(5) . . . . ?
C4 C3 C6 C10 173.8(5) . . . . ?
C11 C3 C6 C8 176.5(4) . . . . ?
C2 C3 C6 C8 -54.0(4) . . . . ?
C4 C3 C6 C8 54.4(4) . . . . ?
C4 C5 C8 C9 -70.5(6) . . . . ?
C4 C5 C8 C6 37.1(6) . . . . ?
C7 C6 C8 C5 61.1(6) . . . . ?
C10 C6 C8 C5 -175.3(5) . . . . ?
C3 C6 C8 C5 -56.1(5) . . . . ?
C7 C6 C8 C9 171.8(5) . . . . ?
C10 C6 C8 C9 -64.5(7) . . . . ?
C3 C6 C8 C9 54.7(5) . . . . ?
C5 C8 C9 C2 70.7(6) . . . . ?
C6 C8 C9 C2 -37.1(6) . . . . ?
N1 C2 C9 C8 124.4(5) . . . . ?
C3 C2 C9 C8 1.9(6) . . . . ?
C2 C3 C11 Br1 59.0(5) . . . . ?
C4 C3 C11 Br1 -62.8(5) . . . . ?
C6 C3 C11 Br1 -178.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H18 O1 0.97 2.50 3.331(6) 143.4 2_665
N1 H4 O1 0.86 2.33 2.995(6) 134.1 2_665
C11 H18 O1 0.97 2.50 3.331(6) 143.4 2_665
N1 H4 O1 0.86 2.33 2.995(6) 134.1 2_665
C11 H18 O1 0.97 2.50 3.331(6) 143.4 2_665
N1 H4 O1 0.86 2.33 2.995(6) 134.1 2_665
C11 H18 O1 0.97 2.50 3.331(6) 143.4 2_665
N1 H4 O1 0.86 2.33 2.995(6) 134.1 2_665
N1 H4 O1 0.86 2.33 2.995(6) 134.1 2_665
C11 H18 O1 0.97 2.50 3.331(6) 143.4 2_665
N1 H4 O1 0.86 2.33 2.995(6) 134.1 2_665
C11 H18 O1 0.97 2.50 3.331(6) 143.4 2_665
N1 H4 O1 0.86 2.33 2.995(6) 134.1 2_665
C11 H18 O1 0.97 2.50 3.331(6) 143.4 2_665
N1 H4 O1 0.86 2.33 2.995(6) 134.1 2_665
C11 H18 O1 0.97 2.50 3.331(6) 143.4 2_665

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.870
_refine_diff_density_rms         0.122


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ether:hexane'
####################################################################### 
# 
# 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 2306786'
loop_
_audit_author_name
_audit_author_address
'Amirbek D. Radzhabov'
;Tomsk Polytechnic University
Russia
;
_audit_update_record             
;
2023-11-09 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_audit_creation_date             2023-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
N-(1-(Bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)trifluoromethanesulfonamide
_chemical_formula_moiety         'C11 H17 Br F3 N O2 S'
_chemical_formula_sum            'C11 H17 Br F3 N O2 S'
_chemical_formula_weight         364.22
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6458(8)
_cell_length_b                   8.4634(10)
_cell_length_c                   11.3756(8)
_cell_angle_alpha                75.804(8)
_cell_angle_beta                 81.317(7)
_cell_angle_gamma                85.101(9)
_cell_volume                     704.55(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3071
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.2790
_cell_measurement_theta_min      2.7070
_shelx_estimated_absorpt_T_max   0.654
_shelx_estimated_absorpt_T_min   0.576
_exptl_absorpt_coefficient_mu    3.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6375
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.485
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  38.00   1.00   10.00    --  -16.00  72.00 -60.00   84
  2  ω   -106.00  10.00   1.00   10.00    --  -16.00 -53.00   0.00  116
  3  ω   -106.00 -34.00   1.00   10.00    --  -16.00 -53.00-180.00   72
  4  ω     41.00  67.00   1.00   10.00    --  -16.00  72.00 -60.00   26
  5  ω    -46.00  17.00   1.00   10.00    --  -16.00  72.00   0.00   63
  6  ω    -39.00  36.00   1.00   10.00    --  -16.00  35.00 -60.00   75
  7  ω    -63.00  47.00   1.00   10.00    --   17.00 -53.00 120.00  110
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1983
_reflns_number_total             2717
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      0.974
_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)+(0.0570P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1012
_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), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C6(H6A,H6B), C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.74715(5) 0.65344(4) 0.10353(4) 0.05263(18) Uani 1 1 d . . . . .
S1 S 0.29548(10) 0.42688(10) 0.40976(7) 0.0244(2) Uani 1 1 d . . . . .
O1 O 0.2994(3) 0.4396(3) 0.53172(18) 0.0313(5) Uani 1 1 d . . . . .
F2 F 0.3572(3) 0.7352(3) 0.3430(2) 0.0577(6) Uani 1 1 d . . . . .
F3 F 0.0833(3) 0.6836(3) 0.3747(2) 0.0598(7) Uani 1 1 d . . . . .
F1 F 0.2456(3) 0.6476(3) 0.21279(18) 0.0642(7) Uani 1 1 d . . . . .
O2 O 0.1710(3) 0.3331(3) 0.3817(2) 0.0387(6) Uani 1 1 d . . . . .
N1 N 0.4882(3) 0.3804(3) 0.3528(2) 0.0252(6) Uani 1 1 d . . . . .
H1 H 0.578278 0.394178 0.388499 0.030 Uiso 1 1 calc R U . . .
C1 C 0.7235(4) 0.3058(4) 0.1913(3) 0.0196(6) Uani 1 1 d . . . . .
C8 C 0.8329(4) 0.4430(4) 0.1965(3) 0.0279(7) Uani 1 1 d . . . . .
H8A H 0.957504 0.420940 0.163482 0.033 Uiso 1 1 calc R U . . .
H8B H 0.829867 0.447665 0.282928 0.033 Uiso 1 1 calc R U . . .
C2 C 0.5246(4) 0.3145(4) 0.2419(3) 0.0246(7) Uani 1 1 d . . . . .
H2 H 0.457692 0.383527 0.176971 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7898(4) 0.1311(4) 0.2580(3) 0.0279(7) Uani 1 1 d . . . . .
C9 C 0.7844(5) 0.1030(5) 0.3971(3) 0.0429(9) Uani 1 1 d . . . . .
H9A H 0.864817 0.175917 0.414636 0.064 Uiso 1 1 calc R U . . .
H9B H 0.821442 -0.010619 0.431458 0.064 Uiso 1 1 calc R U . . .
H9C H 0.663477 0.125841 0.434036 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7237(4) 0.2847(4) 0.0600(3) 0.0323(8) Uani 1 1 d . . . . .
H6A H 0.635248 0.361309 0.017658 0.039 Uiso 1 1 calc R U . . .
H6B H 0.842092 0.303122 0.011364 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2432(5) 0.6357(5) 0.3297(3) 0.0370(9) Uani 1 1 d . . . . .
C3 C 0.4760(4) 0.1342(4) 0.2651(3) 0.0391(9) Uani 1 1 d . . . . .
H3A H 0.438537 0.087979 0.353227 0.047 Uiso 1 1 calc R U . . .
H3B H 0.379468 0.124680 0.218609 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6466(4) 0.0479(4) 0.2201(3) 0.0383(9) Uani 1 1 d . . . . .
H4 H 0.650340 -0.073400 0.250982 0.046 Uiso 1 1 calc R U . . .
C5 C 0.6743(5) 0.1061(5) 0.0800(3) 0.0450(10) Uani 1 1 d . . . . .
H5A H 0.564621 0.099873 0.045279 0.054 Uiso 1 1 calc R U . . .
H5B H 0.771242 0.041036 0.042937 0.054 Uiso 1 1 calc R U . . .
C10 C 0.9786(4) 0.0830(5) 0.2083(4) 0.0436(9) Uani 1 1 d . . . . .
H10A H 0.994072 0.115022 0.118657 0.065 Uiso 1 1 calc R U . . .
H10B H 0.999606 -0.035388 0.235252 0.065 Uiso 1 1 calc R U . . .
H10C H 1.063023 0.138469 0.239020 0.065 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 C8 1.951(3) . ?
S1 O1 1.422(2) . ?
S1 O2 1.408(2) . ?
S1 N1 1.576(2) . ?
S1 C11 1.820(4) . ?
F2 C11 1.311(4) . ?
F3 C11 1.323(4) . ?
F1 C11 1.306(4) . ?
N1 H1 0.8800 . ?
N1 C2 1.480(4) . ?
C1 C8 1.506(4) . ?
C1 C2 1.545(4) . ?
C1 C7 1.567(4) . ?
C1 C6 1.547(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C2 H2 1.0000 . ?
C2 C3 1.551(4) . ?
C7 C9 1.536(4) . ?
C7 C4 1.518(4) . ?
C7 C10 1.528(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.543(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.522(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.535(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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 N1 109.00(13) . . ?
O1 S1 C11 103.30(15) . . ?
O2 S1 O1 121.52(14) . . ?
O2 S1 N1 110.35(13) . . ?
O2 S1 C11 104.90(16) . . ?
N1 S1 C11 106.50(15) . . ?
S1 N1 H1 118.5 . . ?
C2 N1 S1 123.0(2) . . ?
C2 N1 H1 118.5 . . ?
C8 C1 C2 117.5(2) . . ?
C8 C1 C7 115.3(2) . . ?
C8 C1 C6 113.4(2) . . ?
C2 C1 C7 103.7(2) . . ?
C2 C1 C6 103.6(2) . . ?
C6 C1 C7 101.5(2) . . ?
Br1 C8 H8A 109.2 . . ?
Br1 C8 H8B 109.2 . . ?
C1 C8 Br1 112.1(2) . . ?
C1 C8 H8A 109.2 . . ?
C1 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C2 C1 113.3(2) . . ?
N1 C2 H2 109.3 . . ?
N1 C2 C3 113.5(3) . . ?
C1 C2 H2 109.3 . . ?
C1 C2 C3 101.9(2) . . ?
C3 C2 H2 109.3 . . ?
C9 C7 C1 115.2(3) . . ?
C4 C7 C1 93.2(2) . . ?
C4 C7 C9 114.1(3) . . ?
C4 C7 C10 114.4(3) . . ?
C10 C7 C1 113.5(3) . . ?
C10 C7 C9 106.4(3) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C6 H6A 111.0 . . ?
C1 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C5 C6 C1 103.7(3) . . ?
C5 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
F2 C11 S1 111.0(2) . . ?
F2 C11 F3 108.3(3) . . ?
F3 C11 S1 109.6(3) . . ?
F1 C11 S1 111.2(2) . . ?
F1 C11 F2 108.3(3) . . ?
F1 C11 F3 108.4(3) . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 C2 104.1(2) . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C7 C4 C3 103.5(2) . . ?
C7 C4 H4 114.2 . . ?
C7 C4 C5 103.0(3) . . ?
C3 C4 H4 114.2 . . ?
C3 C4 C5 106.6(3) . . ?
C5 C4 H4 114.2 . . ?
C6 C5 H5A 111.3 . . ?
C6 C5 H5B 111.3 . . ?
C4 C5 C6 102.5(3) . . ?
C4 C5 H5A 111.3 . . ?
C4 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
S1 N1 C2 C1 170.3(2) . . . . ?
S1 N1 C2 C3 -74.1(3) . . . . ?
O1 S1 N1 C2 163.0(2) . . . . ?
O1 S1 C11 F2 55.3(2) . . . . ?
O1 S1 C11 F3 -64.2(3) . . . . ?
O1 S1 C11 F1 175.9(2) . . . . ?
O2 S1 N1 C2 27.2(3) . . . . ?
O2 S1 C11 F2 -176.4(2) . . . . ?
O2 S1 C11 F3 64.0(3) . . . . ?
O2 S1 C11 F1 -55.8(3) . . . . ?
N1 S1 C11 F2 -59.4(2) . . . . ?
N1 S1 C11 F3 -179.0(2) . . . . ?
N1 S1 C11 F1 61.2(3) . . . . ?
N1 C2 C3 C4 -124.8(3) . . . . ?
C1 C2 C3 C4 -2.7(3) . . . . ?
C1 C7 C4 C3 -54.5(3) . . . . ?
C1 C7 C4 C5 56.4(3) . . . . ?
C1 C6 C5 C4 1.6(3) . . . . ?
C8 C1 C2 N1 -37.9(4) . . . . ?
C8 C1 C2 C3 -160.2(3) . . . . ?
C8 C1 C7 C9 64.0(3) . . . . ?
C8 C1 C7 C4 -177.4(2) . . . . ?
C8 C1 C7 C10 -59.1(3) . . . . ?
C8 C1 C6 C5 157.7(3) . . . . ?
C2 C1 C8 Br1 -60.4(3) . . . . ?
C2 C1 C7 C9 -65.8(3) . . . . ?
C2 C1 C7 C4 52.8(2) . . . . ?
C2 C1 C7 C10 171.1(2) . . . . ?
C2 C1 C6 C5 -73.9(3) . . . . ?
C2 C3 C4 C7 37.5(3) . . . . ?
C2 C3 C4 C5 -70.7(3) . . . . ?
C7 C1 C8 Br1 176.90(19) . . . . ?
C7 C1 C2 N1 90.5(3) . . . . ?
C7 C1 C2 C3 -31.7(3) . . . . ?
C7 C1 C6 C5 33.4(3) . . . . ?
C7 C4 C5 C6 -37.6(3) . . . . ?
C9 C7 C4 C3 65.0(4) . . . . ?
C9 C7 C4 C5 175.9(3) . . . . ?
C6 C1 C8 Br1 60.5(3) . . . . ?
C6 C1 C2 N1 -163.8(3) . . . . ?
C6 C1 C2 C3 73.9(3) . . . . ?
C6 C1 C7 C9 -173.1(3) . . . . ?
C6 C1 C7 C4 -54.5(3) . . . . ?
C6 C1 C7 C10 63.9(3) . . . . ?
C11 S1 N1 C2 -86.1(3) . . . . ?
C3 C4 C5 C6 70.9(3) . . . . ?
C10 C7 C4 C3 -172.1(3) . . . . ?
C10 C7 C4 C5 -61.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_Garagan_102_20_0m
_database_code_depnum_ccdc_archive 'CCDC 2177719'
loop_
_audit_author_name
_audit_author_address
'Irina Sterkhova'
;Irkutsk Institute of Chemistry Siberian Branch of Russian Academy of Science
Russia
;
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-N-(2-(bromomethyl)-3,3-dimethylbicyclo[2.2.1]heptan-2-yl)-N'-(methylsulfonyl)acetimidamide
_chemical_name_common            ?
_chemical_melting_point          417.3
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H22 Br N2 O2 S'
_chemical_formula_weight         350.29

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.417(7)
_cell_length_b                   16.197(13)
_cell_length_c                   12.549(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.97(3)
_cell_angle_gamma                90
_cell_volume                     1627(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    175
_cell_measurement_theta_min      5
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.655
_shelx_estimated_absorpt_T_min   0.457
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5861
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   IuS
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24712
_diffrn_reflns_av_unetI/netI     0.1640
_diffrn_reflns_av_R_equivalents  0.1664
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.515
_diffrn_reflns_theta_max         30.205
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4684
_reflns_number_gt                2029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0889P)²+0.9183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4684
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2170
_refine_ls_R_factor_gt           0.0839
_refine_ls_wR_factor_ref         0.2111
_refine_ls_wR_factor_gt          0.1712
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.11368(9) 0.73479(5) 0.12963(7) 0.0777(3) Uani 1 1 d . . . . .
S1 S 0.52184(15) 0.84649(8) 0.01406(10) 0.0324(3) Uani 1 1 d . . . . .
O1 O 0.4737(5) 0.7619(2) -0.0179(3) 0.0465(10) Uani 1 1 d . . . . .
O2 O 0.4023(4) 0.8945(2) 0.0496(3) 0.0505(10) Uani 1 1 d . . . . .
N1 N 0.9064(5) 0.8255(3) 0.2676(4) 0.0312(10) Uani 1 1 d . . . . .
N2 N 0.7057(5) 0.8543(2) 0.1017(3) 0.0340(10) Uani 1 1 d . . . . .
C1 C 1.3303(7) 0.9928(4) 0.3417(5) 0.0631(18) Uani 1 1 d . . . . .
H1 H 1.4194 1.0175 0.4017 0.076 Uiso 1 1 calc R U . . .
H16 H 1.3227 1.0210 0.2721 0.076 Uiso 1 1 calc R U . . .
C2 C 1.1623(7) 0.9968(3) 0.3675(5) 0.0498(15) Uani 1 1 d . . . . .
H10 H 1.1459 1.0481 0.4041 0.060 Uiso 1 1 calc R U . . .
C3 C 1.0129(7) 0.9741(3) 0.2622(4) 0.0429(13) Uani 1 1 d . . . . .
C4 C 1.0444(6) 0.8771(3) 0.2497(4) 0.0302(11) Uani 1 1 d . . . . .
C5 C 0.7548(6) 0.8134(3) 0.1970(4) 0.0298(11) Uani 1 1 d . . . . .
C6 C 0.5544(7) 0.8970(4) -0.1016(4) 0.0461(14) Uani 1 1 d . . . . .
H4 H 0.4515 0.8986 -0.1622 0.069 Uiso 1 1 calc R U . . .
H3 H 0.6370 0.8676 -0.1250 0.069 Uiso 1 1 calc R U . . .
H2 H 0.5925 0.9523 -0.0809 0.069 Uiso 1 1 calc R U . . .
C7 C 0.6482(7) 0.7516(3) 0.2348(5) 0.0472(15) Uani 1 1 d . . . . .
H7 H 0.5358 0.7720 0.2164 0.071 Uiso 1 1 calc R U . . .
H5 H 0.6926 0.7439 0.3143 0.071 Uiso 1 1 calc R U . . .
H6 H 0.6484 0.6999 0.1975 0.071 Uiso 1 1 calc R U . . .
C8 C 1.0669(7) 0.8532(3) 0.1375(4) 0.0427(13) Uani 1 1 d . . . . .
H9 H 1.1583 0.8848 0.1263 0.051 Uiso 1 1 calc R U . . .
H8 H 0.9662 0.8671 0.0776 0.051 Uiso 1 1 calc R U . . .
C9 C 1.3605(7) 0.8987(4) 0.3322(5) 0.0557(16) Uani 1 1 d . . . . .
H15 H 1.4615 0.8807 0.3890 0.067 Uiso 1 1 calc R U . . .
H14 H 1.3678 0.8846 0.2587 0.067 Uiso 1 1 calc R U . . .
C10 C 1.2021(6) 0.8606(3) 0.3517(4) 0.0422(13) Uani 1 1 d . . . . .
H11 H 1.2154 0.8027 0.3755 0.051 Uiso 1 1 calc R U . . .
C11 C 1.1750(7) 0.9198(4) 0.4405(4) 0.0502(15) Uani 1 1 d . . . . .
H13 H 1.0730 0.9084 0.4584 0.060 Uiso 1 1 calc R U . . .
H12 H 1.2696 0.9215 0.5084 0.060 Uiso 1 1 calc R U . . .
C12 C 0.8497(7) 0.9933(4) 0.2885(5) 0.0567(16) Uani 1 1 d . . . . .
H19 H 0.8457 1.0510 0.3047 0.085 Uiso 1 1 calc R U . . .
H17 H 0.8458 0.9615 0.3523 0.085 Uiso 1 1 calc R U . . .
H18 H 0.7559 0.9792 0.2251 0.085 Uiso 1 1 calc R U . . .
C13 C 1.0090(8) 1.0261(4) 0.1586(5) 0.0623(17) Uani 1 1 d . . . . .
H22 H 0.9060 1.0162 0.1002 0.093 Uiso 1 1 calc R U . . .
H20 H 1.1012 1.0107 0.1329 0.093 Uiso 1 1 calc R U . . .
H21 H 1.0173 1.0836 0.1781 0.093 Uiso 1 1 calc R U . . .
H23 H 0.932(5) 0.804(3) 0.332(4) 0.020(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C8 1.966(6) . ?
S1 O2 1.447(4) . ?
S1 O1 1.450(4) . ?
S1 N2 1.603(4) . ?
S1 C6 1.760(5) . ?
N1 C5 1.324(6) . ?
N1 C4 1.503(6) . ?
N1 H23 0.84(5) . ?
N2 C5 1.317(6) . ?
C1 C2 1.546(8) . ?
C1 C9 1.556(9) . ?
C1 H1 0.9700 . ?
C1 H16 0.9700 . ?
C2 C11 1.532(8) . ?
C2 C3 1.561(8) . ?
C2 H10 0.9800 . ?
C3 C12 1.540(8) . ?
C3 C13 1.540(7) . ?
C3 C4 1.609(7) . ?
C4 C8 1.528(7) . ?
C4 C10 1.556(7) . ?
C5 C7 1.514(7) . ?
C6 H4 0.9600 . ?
C6 H3 0.9600 . ?
C6 H2 0.9600 . ?
C7 H7 0.9600 . ?
C7 H5 0.9600 . ?
C7 H6 0.9600 . ?
C8 H9 0.9700 . ?
C8 H8 0.9700 . ?
C9 C10 1.556(7) . ?
C9 H15 0.9700 . ?
C9 H14 0.9700 . ?
C10 C11 1.540(8) . ?
C10 H11 0.9800 . ?
C11 H13 0.9700 . ?
C11 H12 0.9700 . ?
C12 H19 0.9600 . ?
C12 H17 0.9600 . ?
C12 H18 0.9600 . ?
C13 H22 0.9600 . ?
C13 H20 0.9600 . ?
C13 H21 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
O2 S1 O1 115.6(2) . . ?
O2 S1 N2 111.2(2) . . ?
O1 S1 N2 113.1(2) . . ?
O2 S1 C6 107.8(3) . . ?
O1 S1 C6 108.2(3) . . ?
N2 S1 C6 99.6(2) . . ?
C5 N1 C4 127.7(4) . . ?
C5 N1 H23 119(3) . . ?
C4 N1 H23 113(3) . . ?
C5 N2 S1 123.3(3) . . ?
C2 C1 C9 103.8(4) . . ?
C2 C1 H1 111.0 . . ?
C9 C1 H1 111.0 . . ?
C2 C1 H16 111.0 . . ?
C9 C1 H16 111.0 . . ?
H1 C1 H16 109.0 . . ?
C11 C2 C1 101.0(5) . . ?
C11 C2 C3 101.8(4) . . ?
C1 C2 C3 111.3(5) . . ?
C11 C2 H10 113.8 . . ?
C1 C2 H10 113.8 . . ?
C3 C2 H10 113.8 . . ?
C12 C3 C13 106.4(5) . . ?
C12 C3 C2 108.0(4) . . ?
C13 C3 C2 112.8(4) . . ?
C12 C3 C4 113.7(4) . . ?
C13 C3 C4 114.3(4) . . ?
C2 C3 C4 101.4(4) . . ?
N1 C4 C8 108.5(4) . . ?
N1 C4 C10 106.4(4) . . ?
C8 C4 C10 113.4(4) . . ?
N1 C4 C3 111.8(4) . . ?
C8 C4 C3 114.1(4) . . ?
C10 C4 C3 102.3(4) . . ?
N2 C5 N1 120.0(4) . . ?
N2 C5 C7 124.4(5) . . ?
N1 C5 C7 115.5(4) . . ?
S1 C6 H4 109.5 . . ?
S1 C6 H3 109.5 . . ?
H4 C6 H3 109.5 . . ?
S1 C6 H2 109.5 . . ?
H4 C6 H2 109.5 . . ?
H3 C6 H2 109.5 . . ?
C5 C7 H7 109.5 . . ?
C5 C7 H5 109.5 . . ?
H7 C7 H5 109.5 . . ?
C5 C7 H6 109.5 . . ?
H7 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
C4 C8 Br1 112.2(3) . . ?
C4 C8 H9 109.2 . . ?
Br1 C8 H9 109.2 . . ?
C4 C8 H8 109.2 . . ?
Br1 C8 H8 109.2 . . ?
H9 C8 H8 107.9 . . ?
C1 C9 C10 102.0(5) . . ?
C1 C9 H15 111.4 . . ?
C10 C9 H15 111.4 . . ?
C1 C9 H14 111.4 . . ?
C10 C9 H14 111.4 . . ?
H15 C9 H14 109.2 . . ?
C11 C10 C4 102.1(4) . . ?
C11 C10 C9 101.1(4) . . ?
C4 C10 C9 110.9(4) . . ?
C11 C10 H11 113.8 . . ?
C4 C10 H11 113.8 . . ?
C9 C10 H11 113.8 . . ?
C2 C11 C10 94.2(4) . . ?
C2 C11 H13 112.9 . . ?
C10 C11 H13 112.9 . . ?
C2 C11 H12 112.9 . . ?
C10 C11 H12 112.9 . . ?
H13 C11 H12 110.3 . . ?
C3 C12 H19 109.5 . . ?
C3 C12 H17 109.5 . . ?
H19 C12 H17 109.5 . . ?
C3 C12 H18 109.5 . . ?
H19 C12 H18 109.5 . . ?
H17 C12 H18 109.5 . . ?
C3 C13 H22 109.5 . . ?
C3 C13 H20 109.5 . . ?
H22 C13 H20 109.5 . . ?
C3 C13 H21 109.5 . . ?
H22 C13 H21 109.5 . . ?
H20 C13 H21 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
O2 S1 N2 C5 78.5(4) . . . . ?
O1 S1 N2 C5 -53.5(5) . . . . ?
C6 S1 N2 C5 -168.1(4) . . . . ?
C9 C1 C2 C11 35.1(6) . . . . ?
C9 C1 C2 C3 -72.4(6) . . . . ?
C11 C2 C3 C12 82.3(5) . . . . ?
C1 C2 C3 C12 -170.8(5) . . . . ?
C11 C2 C3 C13 -160.3(5) . . . . ?
C1 C2 C3 C13 -53.4(6) . . . . ?
C11 C2 C3 C4 -37.6(5) . . . . ?
C1 C2 C3 C4 69.4(5) . . . . ?
C5 N1 C4 C8 -50.1(6) . . . . ?
C5 N1 C4 C10 -172.5(4) . . . . ?
C5 N1 C4 C3 76.6(6) . . . . ?
C12 C3 C4 N1 -0.5(6) . . . . ?
C13 C3 C4 N1 -123.0(5) . . . . ?
C2 C3 C4 N1 115.3(4) . . . . ?
C12 C3 C4 C8 123.1(5) . . . . ?
C13 C3 C4 C8 0.6(6) . . . . ?
C2 C3 C4 C8 -121.1(4) . . . . ?
C12 C3 C4 C10 -114.0(5) . . . . ?
C13 C3 C4 C10 123.5(5) . . . . ?
C2 C3 C4 C10 1.8(5) . . . . ?
S1 N2 C5 N1 -177.1(3) . . . . ?
S1 N2 C5 C7 2.4(7) . . . . ?
C4 N1 C5 N2 -5.9(7) . . . . ?
C4 N1 C5 C7 174.6(4) . . . . ?
N1 C4 C8 Br1 -56.9(5) . . . . ?
C10 C4 C8 Br1 61.1(5) . . . . ?
C3 C4 C8 Br1 177.7(3) . . . . ?
C2 C1 C9 C10 1.1(6) . . . . ?
N1 C4 C10 C11 -83.0(4) . . . . ?
C8 C4 C10 C11 157.8(4) . . . . ?
C3 C4 C10 C11 34.4(5) . . . . ?
N1 C4 C10 C9 170.1(4) . . . . ?
C8 C4 C10 C9 50.8(6) . . . . ?
C3 C4 C10 C9 -72.6(5) . . . . ?
C1 C9 C10 C11 -36.7(5) . . . . ?
C1 C9 C10 C4 70.9(5) . . . . ?
C1 C2 C11 C10 -56.5(5) . . . . ?
C3 C2 C11 C10 58.2(5) . . . . ?
C4 C10 C11 C2 -56.9(5) . . . . ?
C9 C10 C11 C2 57.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H23 O1 0.84(5) 2.10(5) 2.937(6) 173(4) 4_676
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
N1 H23 O1 0.84(5) 2.10(5) 2.937(6) 173(4) 4_676
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
N1 H23 O1 0.84(5) 2.10(5) 2.937(6) 173(4) 4_676
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
N1 H23 O1 0.84(5) 2.10(5) 2.937(6) 173(4) 4_676
C6 H2 O2 0.96 2.51 3.438(7) 162.4 3_675
C7 H5 O1 0.96 2.64 3.455(7) 143.1 4_676
C8 H9 O2 0.97 2.53 3.399(6) 149.5 1_655
C8 H8 N2 0.97 2.31 2.933(7) 120.9 .
N1 H23 O1 0.84(5) 2.10(5) 2.937(6) 173(4) 4_676

_refine_diff_density_max         1.278
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.094


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

data_mo_Astakhova_A83_0m
_database_code_depnum_ccdc_archive 'CCDC 2164790'
loop_
_audit_author_name
_audit_author_address
'Irina Sterkhova'
;Irkutsk institute of Chemistry Siberian Branch of Russian Academy of Science
Russia
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
1,1,1-trifluoro-N-((1E-{(2-iodomethyl)-3,3-dimethylbicyclo[2.2.1]hept-2-yl]amino}methylene)methansulfonamide
_chemical_name_common            ?
_chemical_melting_point          434
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 F3 I N2 O2 S'
_chemical_formula_weight         452.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   32.242(4)
_cell_length_b                   7.9847(9)
_cell_length_c                   13.5491(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.260(4)
_cell_angle_gamma                90
_cell_volume                     3451.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    125
_cell_measurement_theta_min      5
_cell_measurement_theta_max      25

_exptl_crystal_description       colorless
_exptl_crystal_colour            plate
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.012
_shelx_estimated_absorpt_T_min   0.433
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5407
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   IuS
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72361
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.553
_diffrn_reflns_theta_max         30.302
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5163
_reflns_number_gt                3235
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+1.4451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5163
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.21469(2) -0.04234(2) 0.47582(2) 0.05352(9) Uani 1 1 d . . . . .
S1 S 0.07525(2) 0.13250(7) 0.59793(5) 0.03255(15) Uani 1 1 d . . . . .
F1 F 0.01430(5) 0.2945(2) 0.49212(13) 0.0595(5) Uani 1 1 d . . . . .
F2 F 0.06137(5) 0.45499(17) 0.56974(14) 0.0526(4) Uani 1 1 d . . . . .
F3 F 0.01783(5) 0.3286(2) 0.64997(14) 0.0643(5) Uani 1 1 d . . . . .
O1 O 0.04755(6) -0.0068(2) 0.60191(16) 0.0489(5) Uani 1 1 d . . . . .
O2 O 0.10254(6) 0.1736(2) 0.68763(13) 0.0430(4) Uani 1 1 d . . . . .
N1 N 0.10092(6) 0.1451(2) 0.50798(15) 0.0314(4) Uani 1 1 d . . . . .
N2 N 0.11992(6) 0.0791(2) 0.35793(15) 0.0284(4) Uani 1 1 d . . . . .
H17 H 0.1157 0.0128 0.3055 0.034 Uiso 1 1 calc R U . . .
C1 C 0.04027(8) 0.3141(3) 0.5755(2) 0.0417(6) Uani 1 1 d . . . . .
C2 C 0.09587(7) 0.0507(3) 0.42634(19) 0.0290(5) Uani 1 1 d . . . . .
C3 C 0.15335(7) 0.2071(3) 0.35602(18) 0.0280(5) Uani 1 1 d . . . . .
C4 C 0.13445(7) 0.3929(3) 0.3327(2) 0.0348(6) Uani 1 1 d . . . . .
C5 C 0.15003(9) 0.4310(3) 0.2315(2) 0.0427(6) Uani 1 1 d . . . . .
H7 H 0.1343 0.5235 0.1930 0.051 Uiso 1 1 calc R U . . .
C6 C 0.19791(9) 0.4526(3) 0.2440(3) 0.0532(8) Uani 1 1 d . . . . .
H8 H 0.2079 0.5245 0.3021 0.064 Uiso 1 1 calc R U . . .
H1 H 0.2069 0.5018 0.1835 0.064 Uiso 1 1 calc R U . . .
C7 C 0.18386(7) 0.1989(3) 0.45274(19) 0.0340(5) Uani 1 1 d . . . . .
H2 H 0.1685 0.2223 0.5094 0.041 Uiso 1 1 calc R U . . .
H3 H 0.2054 0.2871 0.4518 0.041 Uiso 1 1 calc R U . . .
C8 C 0.14904(10) 0.5231(3) 0.4143(3) 0.0489(7) Uani 1 1 d . . . . .
H4 H 0.1398 0.6349 0.3907 0.073 Uiso 1 1 calc R U . . .
H5 H 0.1797 0.5210 0.4295 0.073 Uiso 1 1 calc R U . . .
H6 H 0.1369 0.4962 0.4746 0.073 Uiso 1 1 calc R U . . .
C9 C 0.21415(8) 0.2716(3) 0.2609(2) 0.0448(7) Uani 1 1 d . . . . .
H13 H 0.2295 0.2353 0.2064 0.054 Uiso 1 1 calc R U . . .
H12 H 0.2328 0.2610 0.3253 0.054 Uiso 1 1 calc R U . . .
C10 C 0.17383(7) 0.1692(3) 0.26099(19) 0.0351(6) Uani 1 1 d . . . . .
H9 H 0.1771 0.0471 0.2477 0.042 Uiso 1 1 calc R U . . .
C11 C 0.14478(9) 0.2610(3) 0.1792(2) 0.0429(6) Uani 1 1 d . . . . .
H11 H 0.1553 0.2602 0.1141 0.052 Uiso 1 1 calc R U . . .
H10 H 0.1156 0.2192 0.1715 0.052 Uiso 1 1 calc R U . . .
C12 C 0.08615(8) 0.3975(3) 0.3157(2) 0.0439(7) Uani 1 1 d . . . . .
H15 H 0.0766 0.5094 0.2929 0.066 Uiso 1 1 calc R U . . .
H14 H 0.0756 0.3715 0.3783 0.066 Uiso 1 1 calc R U . . .
H16 H 0.0755 0.3145 0.2650 0.066 Uiso 1 1 calc R U . . .
C13 C 0.06425(9) -0.0883(4) 0.4047(2) 0.0465(7) Uani 1 1 d . . . . .
H18 H 0.0677 -0.1417 0.3412 0.070 Uiso 1 1 calc R U . . .
H20 H 0.0359 -0.0421 0.4004 0.070 Uiso 1 1 calc R U . . .
H19 H 0.0686 -0.1715 0.4583 0.070 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 C7 2.170(2) . ?
S1 O1 1.4324(18) . ?
S1 O2 1.4324(19) . ?
S1 N1 1.572(2) . ?
S1 C1 1.835(3) . ?
F1 C1 1.315(3) . ?
F2 C1 1.323(3) . ?
F3 C1 1.328(3) . ?
N1 C2 1.329(3) . ?
N2 C2 1.311(3) . ?
N2 C3 1.488(3) . ?
N2 H17 0.8800 . ?
C2 C13 1.507(3) . ?
C3 C7 1.523(3) . ?
C3 C10 1.559(3) . ?
C3 C4 1.618(3) . ?
C4 C12 1.542(3) . ?
C4 C8 1.542(4) . ?
C4 C5 1.557(4) . ?
C5 C11 1.529(4) . ?
C5 C6 1.538(4) . ?
C5 H7 1.0000 . ?
C6 C9 1.543(4) . ?
C6 H8 0.9900 . ?
C6 H1 0.9900 . ?
C7 H2 0.9900 . ?
C7 H3 0.9900 . ?
C8 H4 0.9800 . ?
C8 H5 0.9800 . ?
C8 H6 0.9800 . ?
C9 C10 1.536(3) . ?
C9 H13 0.9900 . ?
C9 H12 0.9900 . ?
C10 C11 1.531(4) . ?
C10 H9 1.0000 . ?
C11 H11 0.9900 . ?
C11 H10 0.9900 . ?
C12 H15 0.9800 . ?
C12 H14 0.9800 . ?
C12 H16 0.9800 . ?
C13 H18 0.9800 . ?
C13 H20 0.9800 . ?
C13 H19 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 117.16(12) . . ?
O1 S1 N1 118.66(11) . . ?
O2 S1 N1 108.39(11) . . ?
O1 S1 C1 104.36(12) . . ?
O2 S1 C1 104.33(12) . . ?
N1 S1 C1 101.57(12) . . ?
C2 N1 S1 126.44(16) . . ?
C2 N2 C3 129.4(2) . . ?
C2 N2 H17 115.3 . . ?
C3 N2 H17 115.3 . . ?
F1 C1 F2 108.7(2) . . ?
F1 C1 F3 108.3(2) . . ?
F2 C1 F3 108.1(2) . . ?
F1 C1 S1 110.39(18) . . ?
F2 C1 S1 111.88(17) . . ?
F3 C1 S1 109.4(2) . . ?
N2 C2 N1 118.5(2) . . ?
N2 C2 C13 116.2(2) . . ?
N1 C2 C13 125.3(2) . . ?
N2 C3 C7 109.62(18) . . ?
N2 C3 C10 105.96(18) . . ?
C7 C3 C10 113.87(18) . . ?
N2 C3 C4 112.32(17) . . ?
C7 C3 C4 112.70(19) . . ?
C10 C3 C4 102.05(18) . . ?
C12 C4 C8 106.8(2) . . ?
C12 C4 C5 108.1(2) . . ?
C8 C4 C5 113.4(2) . . ?
C12 C4 C3 113.27(19) . . ?
C8 C4 C3 114.3(2) . . ?
C5 C4 C3 101.03(19) . . ?
C11 C5 C6 101.2(2) . . ?
C11 C5 C4 101.9(2) . . ?
C6 C5 C4 111.7(2) . . ?
C11 C5 H7 113.6 . . ?
C6 C5 H7 113.6 . . ?
C4 C5 H7 113.6 . . ?
C5 C6 C9 103.0(2) . . ?
C5 C6 H8 111.2 . . ?
C9 C6 H8 111.2 . . ?
C5 C6 H1 111.2 . . ?
C9 C6 H1 111.2 . . ?
H8 C6 H1 109.1 . . ?
C3 C7 I1 112.82(15) . . ?
C3 C7 H2 109.0 . . ?
I1 C7 H2 109.0 . . ?
C3 C7 H3 109.0 . . ?
I1 C7 H3 109.0 . . ?
H2 C7 H3 107.8 . . ?
C4 C8 H4 109.5 . . ?
C4 C8 H5 109.5 . . ?
H4 C8 H5 109.5 . . ?
C4 C8 H6 109.5 . . ?
H4 C8 H6 109.5 . . ?
H5 C8 H6 109.5 . . ?
C10 C9 C6 103.3(2) . . ?
C10 C9 H13 111.1 . . ?
C6 C9 H13 111.1 . . ?
C10 C9 H12 111.1 . . ?
C6 C9 H12 111.1 . . ?
H13 C9 H12 109.1 . . ?
C11 C10 C9 100.0(2) . . ?
C11 C10 C3 102.54(18) . . ?
C9 C10 C3 110.9(2) . . ?
C11 C10 H9 114.0 . . ?
C9 C10 H9 114.0 . . ?
C3 C10 H9 114.0 . . ?
C5 C11 C10 94.3(2) . . ?
C5 C11 H11 112.9 . . ?
C10 C11 H11 112.9 . . ?
C5 C11 H10 112.9 . . ?
C10 C11 H10 112.9 . . ?
H11 C11 H10 110.3 . . ?
C4 C12 H15 109.5 . . ?
C4 C12 H14 109.5 . . ?
H15 C12 H14 109.5 . . ?
C4 C12 H16 109.5 . . ?
H15 C12 H16 109.5 . . ?
H14 C12 H16 109.5 . . ?
C2 C13 H18 109.5 . . ?
C2 C13 H20 109.5 . . ?
H18 C13 H20 109.5 . . ?
C2 C13 H19 109.5 . . ?
H18 C13 H19 109.5 . . ?
H20 C13 H19 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
O1 S1 N1 C2 9.5(3) . . . . ?
O2 S1 N1 C2 146.4(2) . . . . ?
C1 S1 N1 C2 -104.1(2) . . . . ?
O1 S1 C1 F1 -58.8(2) . . . . ?
O2 S1 C1 F1 177.69(18) . . . . ?
N1 S1 C1 F1 65.1(2) . . . . ?
O1 S1 C1 F2 -180.0(2) . . . . ?
O2 S1 C1 F2 56.5(2) . . . . ?
N1 S1 C1 F2 -56.1(2) . . . . ?
O1 S1 C1 F3 60.2(2) . . . . ?
O2 S1 C1 F3 -63.3(2) . . . . ?
N1 S1 C1 F3 -175.88(18) . . . . ?
C3 N2 C2 N1 -0.7(3) . . . . ?
C3 N2 C2 C13 179.1(2) . . . . ?
S1 N1 C2 N2 179.51(17) . . . . ?
S1 N1 C2 C13 -0.2(4) . . . . ?
C2 N2 C3 C7 51.4(3) . . . . ?
C2 N2 C3 C10 174.7(2) . . . . ?
C2 N2 C3 C4 -74.7(3) . . . . ?
N2 C3 C4 C12 -1.0(3) . . . . ?
C7 C3 C4 C12 -125.4(2) . . . . ?
C10 C3 C4 C12 112.1(2) . . . . ?
N2 C3 C4 C8 121.6(2) . . . . ?
C7 C3 C4 C8 -2.8(3) . . . . ?
C10 C3 C4 C8 -125.4(2) . . . . ?
N2 C3 C4 C5 -116.4(2) . . . . ?
C7 C3 C4 C5 119.2(2) . . . . ?
C10 C3 C4 C5 -3.3(2) . . . . ?
C12 C4 C5 C11 -80.4(2) . . . . ?
C8 C4 C5 C11 161.4(2) . . . . ?
C3 C4 C5 C11 38.7(2) . . . . ?
C12 C4 C5 C6 172.3(2) . . . . ?
C8 C4 C5 C6 54.1(3) . . . . ?
C3 C4 C5 C6 -68.6(2) . . . . ?
C11 C5 C6 C9 -33.8(3) . . . . ?
C4 C5 C6 C9 73.9(3) . . . . ?
N2 C3 C7 I1 60.7(2) . . . . ?
C10 C3 C7 I1 -57.8(2) . . . . ?
C4 C3 C7 I1 -173.38(14) . . . . ?
C5 C6 C9 C10 -2.6(3) . . . . ?
C6 C9 C10 C11 38.1(3) . . . . ?
C6 C9 C10 C3 -69.6(3) . . . . ?
N2 C3 C10 C11 84.6(2) . . . . ?
C7 C3 C10 C11 -154.8(2) . . . . ?
C4 C3 C10 C11 -33.1(2) . . . . ?
N2 C3 C10 C9 -169.34(19) . . . . ?
C7 C3 C10 C9 -48.8(3) . . . . ?
C4 C3 C10 C9 73.0(2) . . . . ?
C6 C5 C11 C10 56.4(2) . . . . ?
C4 C5 C11 C10 -58.8(2) . . . . ?
C9 C10 C11 C5 -57.9(2) . . . . ?
C3 C10 C11 C5 56.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H18 O2 0.98 2.52 3.418(3) 152.8 6
C7 H3 I1 0.99 3.32 4.271(2) 161.5 7_556
C7 H2 N1 0.99 2.26 2.911(3) 122.1 .
N2 H17 O2 0.88 2.18 3.056(3) 173.1 6
C13 H18 O2 0.98 2.52 3.418(3) 152.8 6
C7 H3 I1 0.99 3.32 4.271(2) 161.5 7_556
C7 H2 N1 0.99 2.26 2.911(3) 122.1 .
N2 H17 O2 0.88 2.18 3.056(3) 173.1 6
C13 H18 O2 0.98 2.52 3.418(3) 152.8 6
C7 H3 I1 0.99 3.32 4.271(2) 161.5 7_556
C7 H2 N1 0.99 2.26 2.911(3) 122.1 .
N2 H17 O2 0.88 2.18 3.056(3) 173.1 6
C13 H18 O2 0.98 2.52 3.418(3) 152.8 6
C7 H3 I1 0.99 3.32 4.271(2) 161.5 7_556
C7 H2 N1 0.99 2.26 2.911(3) 122.1 .
N2 H17 O2 0.88 2.18 3.056(3) 173.1 6
C13 H18 O2 0.98 2.52 3.418(3) 152.8 6
C7 H3 I1 0.99 3.32 4.271(2) 161.5 7_556
C7 H2 N1 0.99 2.26 2.911(3) 122.1 .
N2 H17 O2 0.88 2.18 3.056(3) 173.1 6
N2 H17 O2 0.88 2.18 3.056(3) 173.1 6
C7 H2 N1 0.99 2.26 2.911(3) 122.1 .
C7 H3 I1 0.99 3.32 4.271(2) 161.5 7_556
C13 H18 O2 0.98 2.52 3.418(3) 152.8 6
N2 H17 O2 0.88 2.18 3.056(3) 173.1 6
C7 H2 N1 0.99 2.26 2.911(3) 122.1 .
C7 H3 I1 0.99 3.32 4.271(2) 161.5 7_556
C13 H18 O2 0.98 2.52 3.418(3) 152.8 6
N2 H17 O2 0.88 2.18 3.056(3) 173.1 6
C7 H2 N1 0.99 2.26 2.911(3) 122.1 .
C7 H3 I1 0.99 3.32 4.271(2) 161.5 7_556
C13 H18 O2 0.98 2.52 3.418(3) 152.8 6
N2 H17 O2 0.88 2.18 3.056(3) 173.1 6
C7 H2 N1 0.99 2.26 2.911(3) 122.1 .
C7 H3 I1 0.99 3.32 4.271(2) 161.5 7_556
C13 H18 O2 0.98 2.52 3.418(3) 152.8 6

_refine_diff_density_max         1.384
_refine_diff_density_min         -1.232
_refine_diff_density_rms         0.087

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
