# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_5aa
_database_code_depnum_ccdc_archive 'CCDC 2109331'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-09-13 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        5aa
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 F3 N2 O S'
_chemical_formula_sum            'C11 H9 F3 N2 O S'
_chemical_formula_weight         274.26

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

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

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

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

_cell_length_a                   8.3925(6)
_cell_length_b                   11.7050(9)
_cell_length_c                   23.1584(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2274.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    925
_cell_measurement_theta_min      2.9920
_cell_measurement_theta_max      22.0060

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.313
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.648
_oxdiff_exptl_absorpt_empirical_full_max 1.391
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5469
_diffrn_reflns_av_unetI/netI     0.1404
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.998
_diffrn_reflns_theta_max         26.239
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2291
_reflns_number_gt                1262
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0002P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2291
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.66271(13) 0.79705(10) 0.36142(5) 0.0169(3) Uani 1 1 d . . . . .
F1 F 0.7937(3) 0.6004(2) 0.20261(12) 0.0306(7) Uani 1 1 d . . . . .
F2 F 0.5421(3) 0.6328(2) 0.20619(12) 0.0290(7) Uani 1 1 d . . . . .
F3 F 0.6941(3) 0.7438(2) 0.15673(11) 0.0341(8) Uani 1 1 d . . . . .
O1 O 0.5244(3) 0.8693(2) 0.36810(13) 0.0216(8) Uani 1 1 d . . . . .
N1 N 0.8241(4) 0.8717(3) 0.35889(17) 0.0181(9) Uani 1 1 d . . . . .
N2 N 0.6535(4) 0.7127(3) 0.30712(16) 0.0190(9) Uani 1 1 d . . . . .
C1 C 0.7066(5) 0.4922(4) 0.5715(2) 0.0306(13) Uani 1 1 d . . . . .
H1A H 0.776808 0.527586 0.600186 0.046 Uiso 1 1 calc R U . . .
H1B H 0.749208 0.417238 0.560631 0.046 Uiso 1 1 calc R U . . .
H1C H 0.599826 0.482839 0.587931 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6974(5) 0.5678(4) 0.5184(2) 0.0231(12) Uani 1 1 d . . . . .
C3 C 0.7965(5) 0.5496(4) 0.4708(2) 0.0206(12) Uani 1 1 d . . . . .
H3 H 0.870525 0.488214 0.471554 0.025 Uiso 1 1 calc R U . . .
C4 C 0.7891(5) 0.6190(4) 0.4229(2) 0.0199(12) Uani 1 1 d . . . . .
H4 H 0.857852 0.605992 0.391006 0.024 Uiso 1 1 calc R U . . .
C5 C 0.6799(5) 0.7082(4) 0.42172(18) 0.0124(10) Uani 1 1 d . . . . .
C6 C 0.5793(5) 0.7281(3) 0.4689(2) 0.0159(11) Uani 1 1 d . . . . .
H6 H 0.505124 0.789351 0.468147 0.019 Uiso 1 1 calc R U . . .
C7 C 0.5893(5) 0.6578(4) 0.5164(2) 0.0200(12) Uani 1 1 d . . . . .
H7 H 0.521115 0.671097 0.548440 0.024 Uiso 1 1 calc R U . . .
C8 C 0.8665(5) 0.9014(4) 0.3052(2) 0.0197(11) Uani 1 1 d . . . . .
H8 H 0.943520 0.960400 0.301526 0.024 Uiso 1 1 calc R U . . .
C9 C 0.8080(5) 0.8536(4) 0.2541(2) 0.0204(12) Uani 1 1 d . . . . .
H9 H 0.832945 0.885842 0.217600 0.024 Uiso 1 1 calc R U . . .
C10 C 0.7132(5) 0.7582(4) 0.2586(2) 0.0169(11) Uani 1 1 d . . . . .
C11 C 0.6851(5) 0.6842(4) 0.2056(2) 0.0215(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.445(3) . ?
S1 N2 1.600(4) . ?
S1 N1 1.613(3) . ?
S1 C5 1.747(4) . ?
F1 C11 1.341(5) . ?
F2 C11 1.342(5) . ?
F3 C11 1.332(5) . ?
N1 C8 1.339(5) . ?
N2 C10 1.340(5) . ?
C1 C2 1.516(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.391(6) . ?
C2 C3 1.398(6) . ?
C3 C4 1.376(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(5) . ?
C6 C7 1.376(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.398(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.521(6) . ?

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 113.97(19) . . ?
O1 S1 N1 111.20(19) . . ?
N2 S1 N1 110.3(2) . . ?
O1 S1 C5 109.2(2) . . ?
N2 S1 C5 105.4(2) . . ?
N1 S1 C5 106.4(2) . . ?
C8 N1 S1 113.4(3) . . ?
C10 N2 S1 113.3(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.5(5) . . ?
C7 C2 C1 120.2(5) . . ?
C3 C2 C1 121.3(4) . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.3(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 S1 121.2(4) . . ?
C6 C5 S1 118.3(3) . . ?
C7 C6 C5 119.2(4) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C2 121.3(5) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
N1 C8 C9 126.1(4) . . ?
N1 C8 H8 117.0 . . ?
C9 C8 H8 117.0 . . ?
C10 C9 C8 117.6(5) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
N2 C10 C9 127.1(5) . . ?
N2 C10 C11 113.1(4) . . ?
C9 C10 C11 119.4(4) . . ?
F3 C11 F1 107.4(4) . . ?
F3 C11 F2 107.1(4) . . ?
F1 C11 F2 106.3(4) . . ?
F3 C11 C10 112.3(4) . . ?
F1 C11 C10 110.7(4) . . ?
F2 C11 C10 112.7(4) . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2109381'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-09-13 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        8
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 Br F3 N2 O S'
_chemical_formula_sum            'C11 H8 Br F3 N2 O S'
_chemical_formula_weight         353.16

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      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                   7.6104(12)
_cell_length_b                   7.8056(14)
_cell_length_c                   12.0015(19)
_cell_angle_alpha                90.867(2)
_cell_angle_beta                 102.061(2)
_cell_angle_gamma                115.696(3)
_cell_volume                     623.71(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1648
_cell_measurement_theta_min      2.9210
_cell_measurement_theta_max      26.3690

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    3.492
_shelx_estimated_absorpt_T_min   0.441
_shelx_estimated_absorpt_T_max   0.818
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.794
_oxdiff_exptl_absorpt_empirical_full_max 1.219
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4226
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.917
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2261
_reflns_number_gt                1815
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2261
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
Br1 Br 0.26035(9) 0.47952(8) 1.11180(4) 0.0343(2) Uani 1 1 d . . . . .
S1 S 0.20851(19) 0.69000(17) 0.74151(10) 0.0225(3) Uani 1 1 d . . . . .
F1 F -0.0099(5) 0.1092(4) 0.7655(3) 0.0376(8) Uani 1 1 d . . . . .
F2 F 0.2028(5) 0.1551(4) 0.9242(3) 0.0408(8) Uani 1 1 d . . . . .
F3 F -0.0820(5) 0.1493(4) 0.9231(3) 0.0383(8) Uani 1 1 d . . . . .
O1 O 0.0386(5) 0.7260(5) 0.7045(3) 0.0283(8) Uani 1 1 d . . . . .
N1 N 0.3644(6) 0.8250(6) 0.8550(4) 0.0261(10) Uani 1 1 d . . . . .
N2 N 0.1440(6) 0.4685(6) 0.7577(3) 0.0222(9) Uani 1 1 d . . . . .
C1 C 0.6601(9) 0.7989(8) 0.3734(5) 0.0346(13) Uani 1 1 d . . . . .
H1A H 0.794838 0.905428 0.399844 0.052 Uiso 1 1 calc R U . . .
H1B H 0.588819 0.826073 0.303315 0.052 Uiso 1 1 calc R U . . .
H1C H 0.670880 0.680863 0.357265 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5473(8) 0.7753(7) 0.4639(4) 0.0261(11) Uani 1 1 d . . . . .
C3 C 0.6403(8) 0.7850(7) 0.5782(4) 0.0267(12) Uani 1 1 d . . . . .
H3 H 0.776568 0.806929 0.597281 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5417(8) 0.7638(7) 0.6641(4) 0.0259(12) Uani 1 1 d . . . . .
H4 H 0.607581 0.770174 0.741705 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3438(8) 0.7331(7) 0.6352(4) 0.0240(11) Uani 1 1 d . . . . .
C6 C 0.2451(8) 0.7226(7) 0.5220(4) 0.0242(11) Uani 1 1 d . . . . .
H6 H 0.109137 0.701651 0.503172 0.029 Uiso 1 1 calc R U . . .
C7 C 0.3481(8) 0.7432(7) 0.4381(4) 0.0271(12) Uani 1 1 d . . . . .
H7 H 0.281619 0.735280 0.360441 0.033 Uiso 1 1 calc R U . . .
C8 C 0.3542(8) 0.7466(7) 0.9522(4) 0.0258(11) Uani 1 1 d . . . . .
H8 H 0.425626 0.830392 1.021556 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2489(8) 0.5534(7) 0.9619(4) 0.0234(11) Uani 1 1 d . . . . .
C10 C 0.1567(7) 0.4216(7) 0.8643(4) 0.0230(11) Uani 1 1 d . . . . .
C11 C 0.0655(8) 0.2070(7) 0.8691(4) 0.0275(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.893(5) . ?
S1 O1 1.424(3) . ?
S1 N1 1.603(4) . ?
S1 N2 1.607(4) . ?
S1 C5 1.751(5) . ?
F1 C11 1.323(6) . ?
F2 C11 1.334(6) . ?
F3 C11 1.326(6) . ?
N1 C8 1.327(6) . ?
N2 C10 1.331(6) . ?
C1 C2 1.487(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.389(7) . ?
C2 C3 1.390(7) . ?
C3 C4 1.370(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(7) . ?
C6 C7 1.371(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.388(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(7) . ?
C10 C11 1.517(7) . ?

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 113.7(2) . . ?
O1 S1 N2 111.9(2) . . ?
N1 S1 N2 110.5(2) . . ?
O1 S1 C5 109.9(2) . . ?
N1 S1 C5 105.9(2) . . ?
N2 S1 C5 104.4(2) . . ?
C8 N1 S1 115.9(4) . . ?
C10 N2 S1 117.6(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.0(5) . . ?
C7 C2 C1 121.8(5) . . ?
C3 C2 C1 120.3(5) . . ?
C4 C3 C2 122.1(5) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.3(5) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 121.5(5) . . ?
C4 C5 S1 119.5(4) . . ?
C6 C5 S1 118.9(4) . . ?
C7 C6 C5 118.6(5) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C2 121.6(5) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N1 C8 C9 126.0(5) . . ?
N1 C8 H8 117.0 . . ?
C9 C8 H8 117.0 . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 Br1 122.5(4) . . ?
C8 C9 Br1 117.4(4) . . ?
N2 C10 C9 124.1(4) . . ?
N2 C10 C11 113.2(4) . . ?
C9 C10 C11 122.6(4) . . ?
F1 C11 F3 107.1(4) . . ?
F1 C11 F2 107.0(4) . . ?
F3 C11 F2 107.5(4) . . ?
F1 C11 C10 112.1(4) . . ?
F3 C11 C10 111.7(4) . . ?
F2 C11 C10 111.1(4) . . ?

_refine_diff_density_max         1.236
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.134

