# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 2311987'
loop_
_audit_author_name
_audit_author_address
'Jiahang Wu'
;State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matte
China
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2023-10-17
_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        ?
_chemical_formula_moiety         'F7 Sb2, C6 H7 N2 O'
_chemical_formula_sum            'C6 H7 F7 N2 O Sb2'
_chemical_formula_weight         499.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Sb Sb -0.5866 1.5461 '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                   7.3227(10)
_cell_length_b                   7.4727(12)
_cell_length_c                   11.1037(16)
_cell_angle_alpha                75.512(13)
_cell_angle_beta                 83.357(11)
_cell_angle_gamma                85.846(13)
_cell_volume                     583.73(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2485
_cell_measurement_temperature    295.68(10)
_cell_measurement_theta_max      29.4210
_cell_measurement_theta_min      4.2460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.843
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5198
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         3.545
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.68(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3468
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00   4.00   1.00    1.00    --  -12.30 -44.00-112.00   89
  2  ω    -27.00  61.00   1.00    1.00    --  -12.30  44.00  38.00   88
  3  ω     35.00  91.00   1.00    1.00    --   12.15 178.00 -60.00   56
  4  ω     36.00  99.00   1.00    1.00    --   12.15-178.00-150.00   63
  5  ω    -18.00  24.00   1.00    1.00    --  -12.30 -99.00-150.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0241948000
_diffrn_orient_matrix_UB_12      -0.0924305000
_diffrn_orient_matrix_UB_13      0.0307017000
_diffrn_orient_matrix_UB_21      -0.0767736000
_diffrn_orient_matrix_UB_22      -0.0311885000
_diffrn_orient_matrix_UB_23      -0.0212335000
_diffrn_orient_matrix_UB_31      0.0552235000
_diffrn_orient_matrix_UB_32      -0.0107110000
_diffrn_orient_matrix_UB_33      -0.0548130000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2035
_reflns_number_total             2558
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       0.0192(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2558
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      0.995
_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)+(0.0172P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0536
_refine_ls_wR_factor_ref         0.0620
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C5(H5), C4(H4), C3(H3)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Sb2 Sb 0.30159(5) 0.19439(5) 0.35902(3) 0.02785(13) Uani 1 1 d . . . . .
Sb1 Sb 0.75804(4) 0.38323(4) 0.45305(2) 0.02787(13) Uani 1 1 d . . . . .
F2 F 0.8906(4) 0.1733(4) 0.5487(2) 0.0375(7) Uani 1 1 d . . . . .
F6 F 0.4063(4) 0.0340(4) 0.2539(2) 0.0454(8) Uani 1 1 d . . . . .
F3 F 0.5472(4) 0.3397(5) 0.5760(3) 0.0528(9) Uani 1 1 d . . . . .
F1 F 0.8370(5) 0.5189(4) 0.5790(2) 0.0489(8) Uani 1 1 d . . . . .
F4 F 0.6363(5) 0.1792(5) 0.3958(3) 0.0544(9) Uani 1 1 d . . . . .
F7 F 0.0787(5) 0.2169(5) 0.2764(3) 0.0608(10) Uani 1 1 d . . . . .
F5 F 0.3971(5) 0.3910(4) 0.2280(3) 0.0591(10) Uani 1 1 d . . . . .
N1 N 0.3416(6) 0.7708(6) 0.1062(3) 0.0330(10) Uani 1 1 d . . . . .
H1 H 0.437153 0.784540 0.140737 0.040 Uiso 1 1 calc R U . . .
O1 O -0.2985(5) 0.7678(7) 0.1221(4) 0.0663(14) Uani 1 1 d . . . . .
C2 C 0.0210(6) 0.7756(6) 0.1116(4) 0.0233(10) Uani 1 1 d . . . . .
N2 N -0.1927(6) 0.8800(7) 0.2677(3) 0.0456(13) Uani 1 1 d . . . . .
H2A H -0.301640 0.901075 0.300826 0.055 Uiso 1 1 calc R U . . .
H2B H -0.098239 0.906118 0.298361 0.055 Uiso 1 1 calc R U . . .
C6 C 0.1753(6) 0.7953(7) 0.1646(4) 0.0281(11) Uani 1 1 d . . . . .
H6 H 0.164422 0.825853 0.241384 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3654(7) 0.7258(7) -0.0041(4) 0.0358(13) Uani 1 1 d . . . . .
H5 H 0.483349 0.710279 -0.042321 0.043 Uiso 1 1 calc R U . . .
C1 C -0.1703(7) 0.8073(7) 0.1693(4) 0.0312(12) Uani 1 1 d . . . . .
C4 C 0.2160(8) 0.7028(8) -0.0600(4) 0.0418(14) Uani 1 1 d . . . . .
H4 H 0.231110 0.669786 -0.136014 0.050 Uiso 1 1 calc R U . . .
C3 C 0.0424(7) 0.7288(7) -0.0032(4) 0.0342(12) Uani 1 1 d . . . . .
H3 H -0.060519 0.715173 -0.041432 0.041 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
Sb2 F6 1.935(3) . ?
Sb2 F1 2.520(3) 2_666 ?
Sb2 F4 2.521(3) . ?
Sb2 F7 1.940(3) . ?
Sb2 F5 1.900(3) . ?
Sb1 F2 1.928(3) . ?
Sb1 F3 1.927(3) . ?
Sb1 F1 2.074(3) . ?
Sb1 F4 2.082(3) . ?
N1 H1 0.8600 . ?
N1 C6 1.335(6) . ?
N1 C5 1.339(6) . ?
O1 C1 1.214(6) . ?
C2 C6 1.366(6) . ?
C2 C1 1.500(6) . ?
C2 C3 1.393(6) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.326(6) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.359(7) . ?
C4 H4 0.9300 . ?
C4 C3 1.375(7) . ?
C3 H3 0.9300 . ?

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
F6 Sb2 F1 159.69(11) . 2_666 ?
F6 Sb2 F4 78.95(12) . . ?
F6 Sb2 F7 87.96(14) . . ?
F1 Sb2 F4 105.64(11) 2_666 . ?
F7 Sb2 F1 82.54(13) . 2_666 ?
F7 Sb2 F4 161.77(11) . . ?
F5 Sb2 F6 85.67(13) . . ?
F5 Sb2 F1 76.25(12) . 2_666 ?
F5 Sb2 F4 77.69(14) . . ?
F5 Sb2 F7 88.81(15) . . ?
F2 Sb1 F1 84.11(12) . . ?
F2 Sb1 F4 82.72(13) . . ?
F3 Sb1 F2 90.68(13) . . ?
F3 Sb1 F1 80.87(13) . . ?
F3 Sb1 F4 79.95(13) . . ?
F1 Sb1 F4 156.53(12) . . ?
Sb1 F1 Sb2 130.13(15) . 2_666 ?
Sb1 F4 Sb2 123.49(16) . . ?
C6 N1 H1 118.7 . . ?
C6 N1 C5 122.5(4) . . ?
C5 N1 H1 118.7 . . ?
C6 C2 C1 123.1(4) . . ?
C6 C2 C3 118.4(4) . . ?
C3 C2 C1 118.4(4) . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
N1 C6 C2 120.0(4) . . ?
N1 C6 H6 120.0 . . ?
C2 C6 H6 120.0 . . ?
N1 C5 H5 120.2 . . ?
N1 C5 C4 119.6(5) . . ?
C4 C5 H5 120.2 . . ?
O1 C1 C2 118.2(4) . . ?
O1 C1 N2 122.8(5) . . ?
N2 C1 C2 119.0(4) . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.5(4) . . ?
C3 C4 H4 120.2 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.1 . . ?

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
N1 C5 C4 C3 0.9(8) . . . . ?
C6 N1 C5 C4 -0.3(7) . . . . ?
C6 C2 C1 O1 -172.4(5) . . . . ?
C6 C2 C1 N2 8.7(7) . . . . ?
C6 C2 C3 C4 0.3(7) . . . . ?
C5 N1 C6 C2 -0.4(7) . . . . ?
C5 C4 C3 C2 -1.0(8) . . . . ?
C1 C2 C6 N1 -177.8(4) . . . . ?
C1 C2 C3 C4 178.6(5) . . . . ?
C3 C2 C6 N1 0.3(7) . . . . ?
C3 C2 C1 O1 9.4(7) . . . . ?
C3 C2 C1 N2 -169.4(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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.186
_oxdiff_exptl_absorpt_empirical_full_min 0.659
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2311988'
loop_
_audit_author_name
_audit_author_address
'Jiahang Wu'
;State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matte
China
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2023-07-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F13 Sb4, C5 H7 N2, C5 H6 N2'
_chemical_formula_sum            'C10 H13 F13 N4 Sb4'
_chemical_formula_weight         923.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.2222(3)
_cell_length_b                   8.1293(4)
_cell_length_c                   10.3779(4)
_cell_angle_alpha                101.002(4)
_cell_angle_beta                 105.247(4)
_cell_angle_gamma                106.829(4)
_cell_volume                     538.65(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6384
_cell_measurement_temperature    250.00(10)
_cell_measurement_theta_max      28.5020
_cell_measurement_theta_min      3.7820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             422
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9297
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         3.338
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  65.00   1.00    1.00    --    6.30  58.00 -48.00   77
  2  ω     -9.00  32.00   1.00    1.00    --    6.30 -58.00 170.00   41
  3  ω    -33.00  61.00   1.00    1.00    --   -7.31  58.00 -48.00   94
  4  ω    -76.00 -23.00   1.00    1.00    --   -7.31 -58.00 170.00   53
  5  ω    -49.00  -5.00   1.00    1.00    --   -7.31 104.00  53.78   44
  6  ω    -66.00 -28.00   1.00    1.00    --   -7.31 132.00-155.59   38
  7  ω    -66.00 -31.00   1.00    1.00    --   -7.31 132.00 -47.32   35
  8  ω    -41.00  69.00   1.00    1.00    --   -7.31  19.00-180.00  110
  9  ω    -27.00  14.00   1.00    1.00    --   -7.31  57.00  30.00   41
 10  ω     36.00  61.00   1.00    1.00    --   -7.31  57.00  30.00   25
 11  ω    -78.00  13.00   1.00    1.00    --   -7.31 -38.00   0.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1071935000
_diffrn_orient_matrix_UB_12      0.0179129000
_diffrn_orient_matrix_UB_13      0.0258723000
_diffrn_orient_matrix_UB_21      0.0150510000
_diffrn_orient_matrix_UB_22      0.0843196000
_diffrn_orient_matrix_UB_23      0.0442656000
_diffrn_orient_matrix_UB_31      -0.0132357000
_diffrn_orient_matrix_UB_32      -0.0404546000
_diffrn_orient_matrix_UB_33      0.0533606000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.974
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                3613
_reflns_number_total             3745
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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         0.482
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details 
;
 Flack x determined using 1680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3745
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0244
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0207P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0486
_refine_ls_wR_factor_ref         0.0504
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), N1(H1), C2(H2), C5(H5), C9(H9), C7(H7), C10(H10), C4(H4), C8(H8)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Sb4 Sb 0.23126(9) -0.12390(8) 0.47003(6) 0.02711(16) Uani 1 1 d . . . . .
Sb1 Sb 0.39722(9) 0.53694(8) 0.63133(6) 0.02841(16) Uani 1 1 d . . . . .
Sb2 Sb 0.77277(9) 0.27328(7) 0.53069(6) 0.02682(16) Uani 1 1 d . . . . .
Sb3 Sb 0.59389(9) -0.26028(8) 0.36500(6) 0.02718(16) Uani 1 1 d . . . . .
F8 F 0.5164(10) 0.0158(9) 0.3594(6) 0.0473(16) Uani 1 1 d . . . . .
F3 F 0.6558(8) 0.6636(8) 0.6155(6) 0.0390(14) Uani 1 1 d . . . . .
F11 F 0.3384(10) -0.3042(9) 0.4045(6) 0.0449(15) Uani 1 1 d . . . . .
F6 F 0.7117(9) 0.0972(7) 0.6275(5) 0.0349(13) Uani 1 1 d . . . . .
F12 F 0.0053(9) -0.3198(9) 0.4760(7) 0.0463(16) Uani 1 1 d . . . . .
F5 F 0.9978(11) 0.4190(9) 0.7058(6) 0.0502(18) Uani 1 1 d . . . . .
F10 F 0.5269(10) -0.5206(8) 0.3212(6) 0.0462(17) Uani 1 1 d . . . . .
F7 F 0.9661(10) 0.1653(9) 0.4866(7) 0.0506(17) Uani 1 1 d . . . . .
F2 F 0.5208(14) 0.6021(11) 0.8321(8) 0.057(2) Uani 1 1 d . . . . .
F13 F 0.0569(11) -0.1616(10) 0.2792(7) 0.0460(18) Uani 1 1 d . . . . .
F1 F 0.3916(10) 0.7978(8) 0.6856(6) 0.0355(15) Uani 1 1 d . . . . .
F9 F 0.4597(14) -0.3024(11) 0.1677(7) 0.059(2) Uani 1 1 d . . . . .
F4 F 0.5291(12) 0.3415(9) 0.6416(8) 0.0586(19) Uani 1 1 d . . . . .
C3 C 0.877(2) 0.1350(18) 1.1600(12) 0.044(3) Uani 1 1 d . . . . .
H3 H 0.945139 0.108567 1.239410 0.053 Uiso 1 1 calc R U . . .
N1 N 0.6626(16) 0.0402(14) 0.9264(11) 0.040(3) Uani 1 1 d . . . . .
H1 H 0.588252 -0.046248 0.849873 0.048 Uiso 1 1 calc R U . . .
N3 N 0.2901(17) -0.0325(17) 0.0780(11) 0.047(3) Uani 1 1 d . . . . .
C6 C 0.214(2) 0.1716(19) -0.0452(13) 0.045(3) Uani 1 1 d . . . . .
C1 C 0.803(2) 0.3515(16) 1.0467(12) 0.036(3) Uani 1 1 d . . . . .
C2 C 0.8989(19) 0.3080(18) 1.1642(12) 0.040(3) Uani 1 1 d . . . . .
H2 H 0.980131 0.399940 1.247516 0.049 Uiso 1 1 calc R U . . .
C5 C 0.6790(18) 0.2040(19) 0.9257(12) 0.044(3) Uani 1 1 d . . . . .
H5 H 0.608097 0.225003 0.844279 0.053 Uiso 1 1 calc R U . . .
N4 N 0.235(2) 0.3329(16) -0.0457(14) 0.068(3) Uani 1 1 d . . . . .
H4A H 0.308538 0.420840 0.030052 0.082 Uiso 1 1 calc R U . . .
H4B H 0.176891 0.354931 -0.121858 0.082 Uiso 1 1 calc R U . . .
C9 C 0.181(2) -0.182(2) -0.0345(16) 0.059(4) Uani 1 1 d . . . . .
H9 H 0.174836 -0.298266 -0.030729 0.071 Uiso 1 1 calc R U . . .
C7 C 0.098(2) 0.015(2) -0.1639(13) 0.055(4) Uani 1 1 d . . . . .
H7 H 0.033072 0.029305 -0.250169 0.066 Uiso 1 1 calc R U . . .
C10 C 0.306(2) 0.133(2) 0.0757(13) 0.049(4) Uani 1 1 d . . . . .
H10 H 0.381550 0.227974 0.158221 0.059 Uiso 1 1 calc R U . . .
N2 N 0.815(2) 0.5172(15) 1.0460(12) 0.064(4) Uani 1 1 d . . . . .
H2A H 0.886087 0.606053 1.121570 0.076 Uiso 1 1 calc R U . . .
H2B H 0.752472 0.537198 0.970035 0.076 Uiso 1 1 calc R U . . .
C4 C 0.755(2) -0.0018(19) 1.0392(15) 0.053(4) Uani 1 1 d . . . . .
H4 H 0.736173 -0.122030 1.036005 0.063 Uiso 1 1 calc R U . . .
C8 C 0.083(2) -0.148(2) -0.1536(16) 0.055(4) Uani 1 1 d . . . . .
H8 H -0.000863 -0.246010 -0.232385 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb4 F11 1.940(6) . ?
Sb4 F12 1.947(6) . ?
Sb4 F13 1.959(6) . ?
Sb4 F1 2.522(6) 1_545 ?
Sb1 F3 1.920(6) . ?
Sb1 F2 1.936(7) . ?
Sb1 F1 2.103(6) . ?
Sb1 F4 2.081(6) . ?
Sb2 F8 2.361(7) . ?
Sb2 F6 1.915(5) . ?
Sb2 F5 1.964(6) . ?
Sb2 F7 1.955(6) . ?
Sb2 F4 2.473(7) . ?
Sb3 F8 2.473(7) . ?
Sb3 F11 1.943(6) . ?
Sb3 F10 1.961(6) . ?
Sb3 F9 1.936(6) . ?
C3 H3 0.9400 . ?
C3 C2 1.359(18) . ?
C3 C4 1.380(18) . ?
N1 H1 0.8700 . ?
N1 C5 1.304(16) . ?
N1 C4 1.344(17) . ?
N3 C9 1.37(2) . ?
N3 C10 1.324(18) . ?
C6 N4 1.276(17) . ?
C6 C7 1.44(2) . ?
C6 C10 1.395(17) . ?
C1 C2 1.398(16) . ?
C1 C5 1.424(17) . ?
C1 N2 1.326(15) . ?
C2 H2 0.9400 . ?
C5 H5 0.9400 . ?
N4 H4A 0.8700 . ?
N4 H4B 0.8700 . ?
C9 H9 0.9400 . ?
C9 C8 1.38(2) . ?
C7 H7 0.9400 . ?
C7 C8 1.33(2) . ?
C10 H10 0.9400 . ?
N2 H2A 0.8700 . ?
N2 H2B 0.8700 . ?
C4 H4 0.9400 . ?
C8 H8 0.9400 . ?

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
F11 Sb4 F12 87.0(3) . . ?
F11 Sb4 F13 90.9(3) . . ?
F11 Sb4 F1 75.4(2) . 1_545 ?
F12 Sb4 F13 86.0(3) . . ?
F12 Sb4 F1 76.8(2) . 1_545 ?
F13 Sb4 F1 158.3(3) . 1_545 ?
F3 Sb1 F2 90.9(3) . . ?
F3 Sb1 F1 82.1(3) . . ?
F3 Sb1 F4 81.1(3) . . ?
F2 Sb1 F1 80.0(3) . . ?
F2 Sb1 F4 81.9(3) . . ?
F4 Sb1 F1 154.9(3) . . ?
F8 Sb2 F4 93.3(3) . . ?
F6 Sb2 F8 74.7(2) . . ?
F6 Sb2 F5 85.6(3) . . ?
F6 Sb2 F7 85.9(3) . . ?
F6 Sb2 F4 74.2(2) . . ?
F5 Sb2 F8 158.9(2) . . ?
F5 Sb2 F4 88.5(3) . . ?
F7 Sb2 F8 85.1(3) . . ?
F7 Sb2 F5 86.0(3) . . ?
F7 Sb2 F4 159.7(2) . . ?
F11 Sb3 F8 75.5(2) . . ?
F11 Sb3 F10 86.3(3) . . ?
F10 Sb3 F8 154.7(2) . . ?
F9 Sb3 F8 77.6(3) . . ?
F9 Sb3 F11 93.3(3) . . ?
F9 Sb3 F10 86.2(3) . . ?
Sb2 F8 Sb3 112.6(2) . . ?
Sb4 F11 Sb3 126.3(3) . . ?
Sb1 F1 Sb4 110.3(2) . 1_565 ?
Sb1 F4 Sb2 129.9(3) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(11) . . ?
C4 C3 H3 120.0 . . ?
C5 N1 H1 118.3 . . ?
C5 N1 C4 123.3(11) . . ?
C4 N1 H1 118.3 . . ?
C10 N3 C9 124.5(12) . . ?
N4 C6 C7 125.2(12) . . ?
N4 C6 C10 121.0(14) . . ?
C10 C6 C7 113.9(13) . . ?
C2 C1 C5 115.8(11) . . ?
N2 C1 C2 123.6(11) . . ?
N2 C1 C5 120.5(11) . . ?
C3 C2 C1 121.2(11) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
N1 C5 C1 120.9(11) . . ?
N1 C5 H5 119.6 . . ?
C1 C5 H5 119.6 . . ?
C6 N4 H4A 120.0 . . ?
C6 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N3 C9 H9 122.9 . . ?
N3 C9 C8 114.2(14) . . ?
C8 C9 H9 122.9 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.1(12) . . ?
C8 C7 H7 119.5 . . ?
N3 C10 C6 122.1(13) . . ?
N3 C10 H10 118.9 . . ?
C6 C10 H10 118.9 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C3 C4 H4 120.7 . . ?
N1 C4 C3 118.7(12) . . ?
N1 C4 H4 120.7 . . ?
C9 C8 H8 117.9 . . ?
C7 C8 C9 124.1(15) . . ?
C7 C8 H8 117.9 . . ?

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
N3 C9 C8 C7 4(2) . . . . ?
C6 C7 C8 C9 -4(2) . . . . ?
C2 C3 C4 N1 1(2) . . . . ?
C2 C1 C5 N1 -1.5(18) . . . . ?
C5 N1 C4 C3 -1.6(19) . . . . ?
C5 C1 C2 C3 1.4(18) . . . . ?
N4 C6 C7 C8 -179.5(14) . . . . ?
N4 C6 C10 N3 -178.1(13) . . . . ?
C9 N3 C10 C6 -1(2) . . . . ?
C7 C6 C10 N3 1.2(19) . . . . ?
C10 N3 C9 C8 -1(2) . . . . ?
C10 C6 C7 C8 1(2) . . . . ?
N2 C1 C2 C3 178.3(13) . . . . ?
N2 C1 C5 N1 -178.6(12) . . . . ?
C4 C3 C2 C1 -1(2) . . . . ?
C4 N1 C5 C1 1.7(18) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.793
_oxdiff_exptl_absorpt_empirical_full_min 0.802
