# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

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

data_c4n4h7osbf4
_database_code_depnum_ccdc_archive 'CCDC 2474438'
loop_
_audit_author_name
_audit_author_address
'zhixiang wang'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2025-07-21 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_audit_creation_date             2024-12-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F4 Sb, C4 H7 N4 O'
_chemical_formula_sum            'C4 H7 F4 N4 O Sb'
_chemical_formula_weight         324.89
_chemical_absolute_configuration ?
_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'
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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   11.4719(5)
_cell_length_b                   4.6982(2)
_cell_length_c                   9.1703(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.104(5)
_cell_angle_gamma                90
_cell_volume                     454.61(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    94
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      26.9270
_cell_measurement_theta_min      8.8470
_shelx_estimated_absorpt_T_max   0.502
_shelx_estimated_absorpt_T_min   0.449
_exptl_absorpt_coefficient_mu    3.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.785
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3418
_diffrn_reflns_point_group_measured_fraction_full 0.804
_diffrn_reflns_point_group_measured_fraction_max 0.595
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.779
_diffrn_reflns_theta_min         1.930
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.785
_diffrn_measurement_device_type  'SuperNova (Mo) X-ray Source'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_full    0.609
_reflns_Friedel_fraction_max     0.403
_reflns_number_gt                1547
_reflns_number_total             1558
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 
;
 Flack x determined using 521 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1558
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0170
_refine_ls_restrained_S_all      1.053
_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)+(0.0199P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0395
_refine_ls_wR_factor_ref         0.0396
_refine_special_details          ?
_olex2_refinement_description    
;
1.a X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
1.b Idealised Me refined as rotating group:
 C4(H4C,H4D,H4E)
;
_atom_sites_solution_hydrogens   mixed
_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
Sb01 Sb 0.77391(2) 0.54322(4) 0.53467(2) 0.01005(9) Uani 1 1 d . . . . .
F3 F 0.9675(3) 0.5647(6) 0.5970(4) 0.0156(6) Uani 1 1 d . . . . .
F2 F 0.8298(3) 0.6321(7) 0.7581(3) 0.0187(6) Uani 1 1 d . . . . .
C1 C 0.1478(7) 0.0711(15) 0.4522(9) 0.0119(17) Uani 1 1 d . . . . .
O1 O 0.2948(3) 0.6052(7) 0.3167(4) 0.0162(7) Uani 1 1 d . . . . .
F1 F 0.6107(3) 0.4477(8) 0.5661(5) 0.0315(8) Uani 1 1 d . . . . .
F4 F 0.8079(3) 0.1429(6) 0.5748(3) 0.0237(7) Uani 1 1 d . . . . .
N4 N 0.0337(4) -0.0266(8) 0.4210(6) 0.0166(9) Uani 1 1 d . . . . .
H4A H -0.032224 0.054020 0.346778 0.020 Uiso 1 1 calc R U . . .
H4B H 0.022786 -0.172865 0.474321 0.020 Uiso 1 1 calc R U . . .
N2 N 0.3780(4) 0.2761(8) 0.5144(4) 0.0120(7) Uani 1 1 d . . . . .
C3 C 0.3593(8) 0.0529(13) 0.5947(9) 0.0113(17) Uani 1 1 d . . . . .
N1 N 0.1625(4) 0.2960(8) 0.3691(5) 0.0121(8) Uani 1 1 d . . . . .
C4 C 0.4739(5) -0.0663(9) 0.7229(6) 0.0144(10) Uani 1 1 d . . . . .
H4C H 0.543138 -0.078389 0.685919 0.022 Uiso 1 1 calc R U . . .
H4D H 0.454887 -0.256770 0.751183 0.022 Uiso 1 1 calc R U . . .
H4E H 0.499265 0.057854 0.816152 0.022 Uiso 1 1 calc R U . . .
C2 C 0.2797(4) 0.4103(10) 0.3937(6) 0.0119(9) Uani 1 1 d . . . . .
N3 N 0.2480(4) -0.0546(8) 0.5699(5) 0.0103(8) Uani 1 1 d . . . . .
H1 H 0.107(6) 0.361(12) 0.299(7) 0.014(14) Uiso 1 1 d . . . . .
H2 H 0.451(6) 0.341(14) 0.539(7) 0.026(16) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sb01 0.00830(12) 0.01082(14) 0.01077(14) -0.0007(3) 0.00347(9) -0.0022(3)
F3 0.0105(14) 0.0208(17) 0.0153(16) 0.0009(12) 0.0049(12) -0.0010(10)
F2 0.0224(14) 0.0215(15) 0.0135(14) -0.0023(11) 0.0084(12) -0.0083(12)
C1 0.015(4) 0.012(3) 0.011(3) 0.003(2) 0.006(3) 0.003(2)
O1 0.0227(17) 0.0130(17) 0.0169(18) 0.0024(13) 0.0121(14) -0.0033(14)
F1 0.0158(16) 0.050(2) 0.035(2) -0.0130(17) 0.0164(16) -0.0170(14)
F4 0.028(2) 0.0104(14) 0.031(2) 0.0005(11) 0.0102(15) -0.0038(11)
N4 0.0080(19) 0.019(2) 0.020(2) 0.0047(17) 0.0026(18) -0.0028(15)
N2 0.0085(18) 0.014(2) 0.015(2) -0.0005(15) 0.0062(15) -0.0023(14)
C3 0.016(4) 0.009(3) 0.010(3) 0.001(2) 0.006(3) 0.003(2)
N1 0.0114(18) 0.013(2) 0.0103(19) 0.0033(15) 0.0027(16) 0.0015(15)
C4 0.010(2) 0.017(3) 0.015(3) 0.0023(17) 0.004(2) 0.0020(17)
C2 0.017(2) 0.009(2) 0.015(3) -0.0034(16) 0.012(2) -0.0008(17)
N3 0.0074(19) 0.010(2) 0.013(2) -0.0008(14) 0.0037(16) 0.0018(13)

_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
Sb01 F3 2.068(3) . ?
Sb01 F2 1.938(3) . ?
Sb01 F1 2.052(3) . ?
Sb01 F4 1.927(3) . ?
C1 N4 1.309(8) . ?
C1 N1 1.352(8) . ?
C1 N3 1.364(8) . ?
O1 C2 1.209(6) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N2 C3 1.347(7) . ?
N2 C2 1.384(6) . ?
N2 H2 0.84(7) . ?
C3 C4 1.487(9) . ?
C3 N3 1.308(9) . ?
N1 C2 1.382(6) . ?
N1 H1 0.77(6) . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4E 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
F2 Sb01 F3 79.81(12) . . ?
F2 Sb01 F1 80.81(13) . . ?
F1 Sb01 F3 155.79(13) . . ?
F4 Sb01 F3 83.12(11) . . ?
F4 Sb01 F2 92.86(13) . . ?
F4 Sb01 F1 83.50(15) . . ?
N4 C1 N1 119.1(6) . . ?
N4 C1 N3 118.8(6) . . ?
N1 C1 N3 122.1(6) . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C3 N2 C2 122.5(5) . . ?
C3 N2 H2 120(4) . . ?
C2 N2 H2 118(4) . . ?
N2 C3 C4 116.4(6) . . ?
N3 C3 N2 124.0(7) . . ?
N3 C3 C4 119.5(6) . . ?
C1 N1 C2 122.7(5) . . ?
C1 N1 H1 122(4) . . ?
C2 N1 H1 115(4) . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4D 109.5 . . ?
C3 C4 H4E 109.5 . . ?
H4C C4 H4D 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
O1 C2 N2 123.6(4) . . ?
O1 C2 N1 123.5(4) . . ?
N1 C2 N2 112.9(4) . . ?
C3 N3 C1 115.7(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
C1 N1 C2 O1 177.5(5) . . . . ?
C1 N1 C2 N2 -1.9(7) . . . . ?
N4 C1 N1 C2 -179.4(5) . . . . ?
N4 C1 N3 C3 179.9(5) . . . . ?
N2 C3 N3 C1 1.2(10) . . . . ?
C3 N2 C2 O1 -177.6(5) . . . . ?
C3 N2 C2 N1 1.7(6) . . . . ?
N1 C1 N3 C3 -1.3(10) . . . . ?
C4 C3 N3 C1 178.7(5) . . . . ?
C2 N2 C3 C4 -179.1(5) . . . . ?
C2 N2 C3 N3 -1.5(9) . . . . ?
N3 C1 N1 C2 1.8(10) . . . . ?

_shelx_res_file                  
;
TITL 1_a.res in Pc
    c4n4h7osbf4.res
    created by SHELXL-2016/6 at 19:40:21 on 14-Nov-2024
REM Old TITL 1_a.res in P2/c
REM SHELXT solution in Pc: R1 0.035, Rweak 0.010, Alpha 0.004
REM <I/s> 0.691 for 112 systematic absences, Orientation as input
REM Flack x = 0.098 ( 0.018 ) from 514 Parsons' quotients
REM Formula found by SHELXT: C5 O2 N3 F4 Sb
CELL 0.71073 11.4719 4.6982 9.1703 90 113.104 90
ZERR 2 0.0005 0.0002 0.0004 0 0.005 0
LATT -1
SYMM +X,-Y,0.5+Z
SFAC C H F N O Sb
UNIT 8 14 8 8 2 2

L.S. 4 0 0
PLAN  5
SIZE 0.26 0.28 0.31
TEMP -173
CONF
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\C4N4H7OSbF4.hkl">
REM </olex2.extras>

WGHT    0.019900
FVAR       0.73821
SB01  6    0.773910    0.543217    0.534670    11.00000    0.00830    0.01082 =
         0.01077   -0.00065    0.00347   -0.00219
F3    3    0.967547    0.564730    0.597039    11.00000    0.01049    0.02076 =
         0.01529    0.00094    0.00487   -0.00097
F2    3    0.829823    0.632100    0.758144    11.00000    0.02237    0.02148 =
         0.01350   -0.00235    0.00845   -0.00830
C1    1    0.147794    0.071086    0.452238    11.00000    0.01478    0.01152 =
         0.01082    0.00322    0.00646    0.00311
O1    5    0.294807    0.605204    0.316736    11.00000    0.02273    0.01304 =
         0.01687    0.00242    0.01206   -0.00332
F1    3    0.610744    0.447748    0.566080    11.00000    0.01579    0.04971 =
         0.03490   -0.01300    0.01644   -0.01702
F4    3    0.807858    0.142897    0.574845    11.00000    0.02815    0.01035 =
         0.03124    0.00052    0.01023   -0.00379
N4    4    0.033654   -0.026587    0.421038    11.00000    0.00802    0.01885 =
         0.02020    0.00475    0.00264   -0.00281
AFIX  93
H4A   2   -0.032224    0.054020    0.346778    11.00000   -1.20000
H4B   2    0.022786   -0.172865    0.474321    11.00000   -1.20000
AFIX   0
N2    4    0.378037    0.276085    0.514369    11.00000    0.00850    0.01375 =
         0.01530   -0.00054    0.00624   -0.00232
C3    1    0.359336    0.052881    0.594746    11.00000    0.01614    0.00853 =
         0.01035    0.00099    0.00643    0.00300
N1    4    0.162504    0.296003    0.369061    11.00000    0.01139    0.01321 =
         0.01026    0.00328    0.00275    0.00149
C4    1    0.473919   -0.066257    0.722921    11.00000    0.01007    0.01680 =
         0.01520    0.00226    0.00381    0.00196
AFIX 137
H4C   2    0.543138   -0.078389    0.685919    11.00000   -1.50000
H4D   2    0.454887   -0.256770    0.751183    11.00000   -1.50000
H4E   2    0.499265    0.057854    0.816152    11.00000   -1.50000
AFIX   0
C2    1    0.279707    0.410262    0.393669    11.00000    0.01708    0.00910 =
         0.01452   -0.00342    0.01172   -0.00085
N3    4    0.248005   -0.054580    0.569902    11.00000    0.00737    0.01048 =
         0.01270   -0.00076    0.00367    0.00183
H1    2    0.106734    0.360775    0.298936    11.00000    0.01394
H2    2    0.451311    0.341233    0.538969    11.00000    0.02631
HKLF 4




REM  1_a.res in Pc
REM R1 =  0.0170 for    1547 Fo > 4sig(Fo)  and  0.0171 for all    1558 data
REM    136 parameters refined using      2 restraints

END

WGHT      0.0199      0.0000

REM Highest difference peak  0.446,  deepest hole -0.795,  1-sigma level  0.091
Q1    1   0.6987  0.5763  0.4280  11.00000  0.05    0.45
Q2    1   0.8415  0.5540  0.6360  11.00000  0.05    0.44
Q3    1   0.7796  0.5066  0.6865  11.00000  0.05    0.44
Q4    1   0.7669  0.5076  0.3779  11.00000  0.05    0.38
Q5    1   0.8410  0.6898  0.8966  11.00000  0.05    0.35
;
_shelx_res_checksum              9598
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2474439'
loop_
_audit_author_name
_audit_author_address
'zhixiang wang'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2025-07-21 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_audit_creation_date             2025-05-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F4 Sb, C4 H8 N5'
_chemical_formula_sum            'C4 H8 F4 N5 Sb'
_chemical_formula_weight         323.90
_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           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                   5.0998(3)
_cell_length_b                   9.4607(5)
_cell_length_c                   10.3378(6)
_cell_angle_alpha                68.330(5)
_cell_angle_beta                 77.847(5)
_cell_angle_gamma                85.276(5)
_cell_volume                     453.13(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6009
_cell_measurement_temperature    294.21(10)
_cell_measurement_theta_max      29.4910
_cell_measurement_theta_min      4.0090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10634
_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    2.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blky
_exptl_crystal_F_000             308
_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  0.0454
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8512
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.316
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.21(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3468
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  54.00   1.00    1.00    --    9.18  56.00 172.00   32
  2  ω     -5.00  21.00   1.00    1.00    --    9.18 -56.00  30.00   26
  3  ω    -34.00  59.00   1.00    1.00    --   -9.33  56.00 172.00   93
  4  ω    -78.00   6.00   1.00    1.00    --   -9.33 -56.00  30.00   84
  5  ω    -59.00  34.00   1.00    1.00    --    9.18 -55.00 -13.36   93
  6  ω    -11.00  74.00   1.00    1.00    --    9.18  38.00 -30.00   85
  7  ω    -20.00  46.00   1.00    1.00    --    9.18 -99.00 -90.00   66
  8  ω     43.00  68.00   1.00    1.00    --    9.18-134.00  -8.77   25
  9  ω    -76.00 -49.00   1.00    1.00    --   -9.33 145.00 -18.85   27
 10  ω    -20.00  23.00   1.00    1.00    --   -9.33 -99.00 -60.00   43
 11  ω    -84.00 -42.00   1.00    1.00    --   -9.33 156.00  81.85   42
 12  ω    -50.00   3.00   1.00    1.00    --   -9.33 -38.00 150.00   53
;
_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      0.1392137000
_diffrn_orient_matrix_UB_12      -0.0169853000
_diffrn_orient_matrix_UB_13      -0.0099077000
_diffrn_orient_matrix_UB_21      -0.0270661000
_diffrn_orient_matrix_UB_22      -0.0750801000
_diffrn_orient_matrix_UB_23      0.0494315000
_diffrn_orient_matrix_UB_31      -0.0113554000
_diffrn_orient_matrix_UB_32      -0.0241483000
_diffrn_orient_matrix_UB_33      -0.0558883000
_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                1761
_reflns_number_total             1850
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       0.055(2)
_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   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1850
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0268P)²+0.0243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0504
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 N5(H5)
1.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N2(H2A,H2B)
1.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Sb1 Sb 0.82111(3) 0.87495(2) 0.41909(2) 0.02367(11) Uani 1 1 d . . . . .
F3 F 1.1143(4) 0.85150(19) 0.53160(18) 0.0360(4) Uani 1 1 d . . . . .
F2 F 0.9649(4) 0.67720(19) 0.42248(18) 0.0371(4) Uani 1 1 d . . . . .
F4 F 1.0859(4) 0.99410(19) 0.26387(16) 0.0361(4) Uani 1 1 d . . . . .
F1 F 0.6804(4) 0.8525(2) 0.25445(19) 0.0441(5) Uani 1 1 d . . . . .
N3 N 0.4127(5) 0.3757(3) 0.2605(2) 0.0245(5) Uani 1 1 d . . . . .
N4 N 0.6899(5) 0.4515(3) 0.3700(2) 0.0290(5) Uani 1 1 d . . . . .
H4A H 0.722331 0.357747 0.416588 0.035 Uiso 1 1 calc R U . . .
H4B H 0.764054 0.522558 0.382657 0.035 Uiso 1 1 calc R U . . .
N2 N 0.1354(5) 0.3187(3) 0.1398(2) 0.0291(5) Uani 1 1 d . . . . .
H2A H 0.157182 0.223662 0.186630 0.035 Uiso 1 1 calc R U . . .
H2B H 0.034404 0.346243 0.077646 0.035 Uiso 1 1 calc R U . . .
N1 N 0.2102(5) 0.5696(3) 0.0834(2) 0.0241(5) Uani 1 1 d . . . . .
N5 N 0.4813(5) 0.6346(3) 0.2063(2) 0.0255(5) Uani 1 1 d . . . . .
H5 H 0.552024 0.704496 0.222246 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5267(5) 0.4862(3) 0.2795(3) 0.0222(5) Uani 1 1 d . . . . .
C2 C 0.3248(6) 0.6724(3) 0.1082(3) 0.0235(6) Uani 1 1 d . . . . .
C3 C 0.2563(5) 0.4216(3) 0.1631(2) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.2856(7) 0.8358(3) 0.0290(3) 0.0361(7) Uani 1 1 d . . . . .
H1A H 0.428671 0.871027 -0.051994 0.043 Uiso 1 1 calc R U . . .
H1B H 0.285232 0.892140 0.089563 0.043 Uiso 1 1 calc R U . . .
H1C H 0.117311 0.850402 -0.001974 0.043 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sb1 0.02775(15) 0.01783(14) 0.02784(14) -0.00757(9) -0.01162(8) -0.00046(8)
F3 0.0451(11) 0.0244(9) 0.0456(10) -0.0107(8) -0.0280(8) 0.0027(8)
F2 0.0477(11) 0.0211(9) 0.0503(10) -0.0157(8) -0.0234(8) 0.0059(8)
F4 0.0451(11) 0.0264(9) 0.0339(8) -0.0076(7) -0.0039(7) -0.0100(8)
F1 0.0614(13) 0.0329(10) 0.0499(10) -0.0147(9) -0.0360(10) -0.0018(9)
N3 0.0286(13) 0.0199(12) 0.0265(11) -0.0064(9) -0.0116(9) -0.0014(10)
N4 0.0327(14) 0.0259(13) 0.0338(12) -0.0113(10) -0.0174(10) 0.0011(10)
N2 0.0398(15) 0.0179(12) 0.0320(12) -0.0048(10) -0.0182(10) -0.0036(10)
N1 0.0295(13) 0.0182(12) 0.0257(11) -0.0054(9) -0.0119(9) -0.0021(10)
N5 0.0304(13) 0.0196(12) 0.0295(12) -0.0084(9) -0.0120(9) -0.0025(10)
C4 0.0221(14) 0.0220(14) 0.0239(13) -0.0095(11) -0.0053(10) 0.0001(11)
C2 0.0267(14) 0.0215(14) 0.0233(12) -0.0078(11) -0.0072(10) -0.0008(11)
C3 0.0234(14) 0.0219(13) 0.0193(12) -0.0063(10) -0.0042(10) -0.0037(11)
C1 0.049(2) 0.0196(15) 0.0433(16) -0.0084(13) -0.0229(14) 0.0001(14)

_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
Sb1 F3 2.0311(15) . ?
Sb1 F2 1.9430(16) . ?
Sb1 F4 1.9161(16) . ?
Sb1 F1 2.0646(16) . ?
N3 C4 1.330(3) . ?
N3 C3 1.340(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C4 1.316(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C3 1.312(3) . ?
N1 C2 1.302(3) . ?
N1 C3 1.368(3) . ?
N5 H5 0.8600 . ?
N5 C4 1.354(4) . ?
N5 C2 1.348(3) . ?
C2 C1 1.478(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
F3 Sb1 F1 151.40(9) . . ?
F2 Sb1 F3 79.89(7) . . ?
F2 Sb1 F1 78.30(7) . . ?
F4 Sb1 F3 83.24(7) . . ?
F4 Sb1 F2 96.63(8) . . ?
F4 Sb1 F1 81.15(8) . . ?
C4 N3 C3 115.6(2) . . ?
H4A N4 H4B 120.0 . . ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
C2 N1 C3 116.1(2) . . ?
C4 N5 H5 120.1 . . ?
C2 N5 H5 120.1 . . ?
C2 N5 C4 119.7(2) . . ?
N3 C4 N5 121.4(2) . . ?
N4 C4 N3 119.7(2) . . ?
N4 C4 N5 118.9(2) . . ?
N1 C2 N5 121.8(2) . . ?
N1 C2 C1 120.5(2) . . ?
N5 C2 C1 117.8(2) . . ?
N3 C3 N1 125.3(2) . . ?
N2 C3 N3 118.9(2) . . ?
N2 C3 N1 115.8(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
C4 N3 C3 N2 -179.4(2) . . . . ?
C4 N3 C3 N1 0.8(4) . . . . ?
C4 N5 C2 N1 1.4(4) . . . . ?
C4 N5 C2 C1 -178.8(3) . . . . ?
C2 N1 C3 N3 -1.6(4) . . . . ?
C2 N1 C3 N2 178.5(2) . . . . ?
C2 N5 C4 N3 -2.3(4) . . . . ?
C2 N5 C4 N4 176.9(2) . . . . ?
C3 N3 C4 N4 -178.0(2) . . . . ?
C3 N3 C4 N5 1.2(4) . . . . ?
C3 N1 C2 N5 0.4(4) . . . . ?
C3 N1 C2 C1 -179.3(3) . . . . ?

_shelx_res_file                  
;
TITL 1_a.res in P-1
    1.res
    created by SHELXL-2018/3 at 14:42:55 on 23-Apr-2025
REM Old TITL 1 in P1
REM SHELXT solution in P-1: R1 0.086, Rweak 0.014, Alpha 0.032
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C8 O3 Sb F2
CELL 0.71073 5.0998 9.4607 10.3378 68.33 77.847 85.276
ZERR 2 0.0003 0.0005 0.0006 0.005 0.005 0.005
LATT 1
SFAC C H F N Sb
UNIT 8 16 8 10 2

L.S. 4 0 0
PLAN  5
TEMP 21
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\1.hkl">
REM </olex2.extras>

WGHT    0.026800    0.024300
EXTI    0.055186
FVAR       0.71899
SB1   5    0.821108    0.874946    0.419087    11.00000    0.02775    0.01783 =
         0.02784   -0.00757   -0.01162   -0.00046
F3    3    1.114332    0.851502    0.531604    11.00000    0.04506    0.02439 =
         0.04557   -0.01074   -0.02796    0.00271
F2    3    0.964925    0.677204    0.422484    11.00000    0.04774    0.02108 =
         0.05029   -0.01572   -0.02338    0.00586
F4    3    1.085868    0.994105    0.263868    11.00000    0.04509    0.02642 =
         0.03386   -0.00765   -0.00389   -0.00995
F1    3    0.680397    0.852512    0.254454    11.00000    0.06139    0.03287 =
         0.04990   -0.01467   -0.03596   -0.00183
N3    4    0.412697    0.375723    0.260507    11.00000    0.02861    0.01988 =
         0.02646   -0.00635   -0.01160   -0.00140
N4    4    0.689884    0.451486    0.370043    11.00000    0.03268    0.02592 =
         0.03380   -0.01127   -0.01741    0.00107
AFIX  93
H4A   2    0.722331    0.357747    0.416588    11.00000   -1.20000
H4B   2    0.764054    0.522558    0.382657    11.00000   -1.20000
AFIX   0
N2    4    0.135424    0.318680    0.139788    11.00000    0.03981    0.01790 =
         0.03199   -0.00484   -0.01819   -0.00359
AFIX  93
H2A   2    0.157182    0.223662    0.186630    11.00000   -1.20000
H2B   2    0.034404    0.346243    0.077646    11.00000   -1.20000
AFIX   0
N1    4    0.210202    0.569611    0.083399    11.00000    0.02951    0.01825 =
         0.02567   -0.00537   -0.01193   -0.00206
N5    4    0.481315    0.634595    0.206278    11.00000    0.03044    0.01960 =
         0.02948   -0.00837   -0.01200   -0.00250
AFIX  43
H5    2    0.552024    0.704496    0.222246    11.00000   -1.20000
AFIX   0
C4    1    0.526709    0.486178    0.279501    11.00000    0.02212    0.02204 =
         0.02387   -0.00951   -0.00535    0.00009
C2    1    0.324835    0.672372    0.108234    11.00000    0.02670    0.02147 =
         0.02332   -0.00776   -0.00716   -0.00079
C3    1    0.256325    0.421568    0.163123    11.00000    0.02339    0.02188 =
         0.01934   -0.00626   -0.00421   -0.00372
C1    1    0.285572    0.835804    0.029017    11.00000    0.04939    0.01964 =
         0.04331   -0.00842   -0.02290    0.00007
AFIX 137
H1A   2    0.428671    0.871027   -0.051994    11.00000   -1.20000
H1B   2    0.285232    0.892140    0.089563    11.00000   -1.20000
H1C   2    0.117311    0.850402   -0.001974    11.00000   -1.20000
AFIX   0
HKLF 4




REM  1_a.res in P-1
REM wR2 = 0.0504, GooF = S = 1.065, Restrained GooF = 1.065 for all data
REM R1 = 0.0203 for 1761 Fo > 4sig(Fo) and 0.0217 for all 1850 data
REM 129 parameters refined using 0 restraints

END

WGHT      0.0268      0.0243

REM Highest difference peak  0.468,  deepest hole -0.545,  1-sigma level  0.100
Q1    1   0.9603  0.8804  0.5077  11.00000  0.05    0.47
Q2    1   0.6792  0.8987  0.3466  11.00000  0.05    0.46
Q3    1   0.4888  0.4301  0.2631  11.00000  0.05    0.44
Q4    1   0.6881  0.9787  0.4094  11.00000  0.05    0.43
Q5    1   1.0114  0.8398  0.4621  11.00000  0.05    0.40
;
_shelx_res_checksum              16745
_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 5.978
_oxdiff_exptl_absorpt_empirical_full_min 0.557
