# 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_xh063
_database_code_depnum_ccdc_archive 'CCDC 2312629'
loop_
_audit_author_name
_audit_author_address
'Alexander Nitzer'
;Ludwig Maximilian University Munich
Germany
;
_audit_update_record             
;
2023-12-07 deposited with the CCDC.	2024-07-08 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           SHELXL-2018/3
_audit_creation_date             2020-12-08
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H4 F4 O, F6 Sb'
_chemical_formula_sum            'C2 H3 F10 O Sb'
_chemical_formula_weight         354.79

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'
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'
Sb Sb -0.5866 1.5461 '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                   6.3267(5)
_cell_length_b                   7.8117(5)
_cell_length_c                   8.5217(5)
_cell_angle_alpha                85.971(5)
_cell_angle_beta                 87.605(6)
_cell_angle_gamma                85.482(6)
_cell_volume                     418.54(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2881
_cell_measurement_theta_min      2.6060
_cell_measurement_theta_max      31.2130

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.815
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.118
_exptl_absorpt_coefficient_mu    3.437
_shelx_estimated_absorpt_T_min   0.360
_shelx_estimated_absorpt_T_max   0.687
_exptl_absorpt_correction_T_min  0.59154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.817
_oxdiff_exptl_absorpt_empirical_full_max 1.581
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100(2) # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            8217
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.398
_diffrn_reflns_theta_max         30.507
_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             2548
_reflns_number_gt                2248
_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    
'SHELXT (Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP-3, Version ORTEP-III (1.0.3), L. J. Farrugia, J. Appl. Cryst. (2012),45, 849-854'
_computing_publication_material  
'PLATON (A.L.Spek, Acta Cryst. 2009, D65, 148-155.) '
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2548
_refine_ls_number_parameters     139
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0558
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
Sb1 Sb 0.72115(3) 0.04077(2) 0.74191(2) 0.01408(7) Uani 1 1 d . . . . .
F5 F 0.6000(3) 0.2373(2) 0.8475(2) 0.0179(4) Uani 1 1 d . . . . .
F6 F 0.9926(3) 0.1018(2) 0.8007(2) 0.0239(4) Uani 1 1 d . . . . .
F7 F 0.7454(3) 0.1893(3) 0.5636(2) 0.0273(5) Uani 1 1 d . . . . .
F9 F 0.7062(3) -0.0882(2) 0.9331(2) 0.0250(4) Uani 1 1 d . . . . .
F10 F 0.4453(3) -0.0018(2) 0.6969(2) 0.0248(4) Uani 1 1 d . . . . .
F8 F 0.8464(3) -0.1452(2) 0.6399(2) 0.0285(5) Uani 1 1 d . . . . .
F3 F 0.1330(3) 0.6742(3) 0.9084(2) 0.0306(5) Uani 1 1 d . . . . .
F1 F -0.0201(3) 0.4832(3) 0.6944(3) 0.0340(5) Uani 1 1 d . . . . .
F2 F 0.2943(4) 0.4361(3) 0.5885(2) 0.0345(5) Uani 1 1 d . . . . .
O1 O 0.2231(4) 0.3363(3) 0.8359(3) 0.0179(5) Uani 1 1 d D . . . .
F4 F 0.4561(3) 0.6087(3) 0.8211(3) 0.0305(5) Uani 1 1 d . . . . .
C2 C 0.2530(5) 0.6393(4) 0.7795(4) 0.0191(6) Uani 1 1 d . . . . .
C1 C 0.1849(5) 0.4737(4) 0.7192(4) 0.0195(6) Uani 1 1 d . . . . .
H3 H 0.248(6) 0.727(4) 0.705(4) 0.021(9) Uiso 1 1 d . . . . .
H1 H 0.133(8) 0.256(6) 0.829(5) 0.056(15) Uiso 1 1 d . . . . .
H2 H 0.350(4) 0.305(6) 0.852(5) 0.054(15) Uiso 1 1 d 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
Sb1 0.01197(11) 0.01335(10) 0.01674(11) 0.00080(7) -0.00092(7) -0.00135(7)
F5 0.0150(9) 0.0161(9) 0.0228(9) -0.0038(7) -0.0023(7) 0.0004(7)
F6 0.0118(9) 0.0227(10) 0.0374(11) 0.0006(8) -0.0036(8) -0.0044(7)
F7 0.0355(12) 0.0272(10) 0.0173(9) 0.0066(8) 0.0022(8) 0.0000(9)
F9 0.0232(11) 0.0249(10) 0.0248(10) 0.0121(8) 0.0005(8) -0.0008(8)
F10 0.0149(10) 0.0252(10) 0.0356(11) -0.0045(8) -0.0080(8) -0.0037(8)
F8 0.0261(11) 0.0226(10) 0.0368(12) -0.0104(9) 0.0004(9) 0.0040(8)
F3 0.0365(13) 0.0308(11) 0.0242(10) -0.0068(9) -0.0006(9) 0.0030(9)
F1 0.0268(12) 0.0234(10) 0.0527(14) 0.0052(10) -0.0234(10) -0.0028(9)
F2 0.0586(16) 0.0279(11) 0.0162(10) -0.0023(8) 0.0024(10) 0.0016(10)
O1 0.0140(12) 0.0148(11) 0.0242(12) 0.0053(9) -0.0026(9) -0.0020(9)
F4 0.0207(11) 0.0220(10) 0.0495(13) -0.0007(9) -0.0097(9) -0.0041(8)
C2 0.0224(17) 0.0171(15) 0.0176(15) 0.0014(12) -0.0026(13) -0.0017(12)
C1 0.0224(17) 0.0178(15) 0.0182(15) 0.0028(12) -0.0055(13) -0.0016(12)

_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 F8 1.8528(18) . ?
Sb1 F7 1.8544(17) . ?
Sb1 F9 1.8574(17) . ?
Sb1 F10 1.8624(19) . ?
Sb1 F6 1.914(2) . ?
Sb1 F5 1.9248(17) . ?
F3 C2 1.341(4) . ?
F1 C1 1.318(4) . ?
F2 C1 1.325(4) . ?
O1 C1 1.424(4) . ?
F4 C2 1.346(4) . ?
C2 C1 1.524(5) . ?

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
F8 Sb1 F7 92.69(9) . . ?
F8 Sb1 F9 92.10(9) . . ?
F7 Sb1 F9 173.57(9) . . ?
F8 Sb1 F10 94.62(9) . . ?
F7 Sb1 F10 92.02(9) . . ?
F9 Sb1 F10 91.86(9) . . ?
F8 Sb1 F6 90.97(9) . . ?
F7 Sb1 F6 88.35(9) . . ?
F9 Sb1 F6 87.29(9) . . ?
F10 Sb1 F6 174.37(8) . . ?
F8 Sb1 F5 178.08(8) . . ?
F7 Sb1 F5 86.62(8) . . ?
F9 Sb1 F5 88.45(8) . . ?
F10 Sb1 F5 87.20(8) . . ?
F6 Sb1 F5 87.21(8) . . ?
F3 C2 F4 108.5(3) . . ?
F3 C2 C1 108.1(3) . . ?
F4 C2 C1 107.2(3) . . ?
F1 C1 F2 110.0(3) . . ?
F1 C1 O1 106.3(3) . . ?
F2 C1 O1 108.8(2) . . ?
F1 C1 C2 111.9(3) . . ?
F2 C1 C2 110.6(3) . . ?
O1 C1 C2 109.1(3) . . ?

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
F3 C2 C1 F1 55.0(3) . . . . ?
F4 C2 C1 F1 171.8(2) . . . . ?
F3 C2 C1 F2 178.0(2) . . . . ?
F4 C2 C1 F2 -65.2(3) . . . . ?
F3 C2 C1 O1 -62.4(3) . . . . ?
F4 C2 C1 O1 54.5(3) . . . . ?

_refine_diff_density_max         1.199
_refine_diff_density_min         -1.246
_refine_diff_density_rms         0.168

_shelx_res_file                  
;
TITL shelxt_a.res in P-1
    shelx.res
    created by SHELXL-2018/3 at 17:22:15 on 08-Dec-2020
CELL  0.71073   6.3267   7.8117   8.5217   85.971   87.605   85.482
ZERR     2.00   0.0005   0.0005   0.0005    0.005    0.006    0.006
LATT   1
SFAC  C    H    O    F    SB
UNIT  4 6 2 20 2
MERG   2
DFIX    0.82 O1 H2
SHEL1000        0.70
FMAP   2
PLAN   20
SIZE     0.118   0.154   0.373
ACTA
BOND
CONF
LIST   6
L.S.  10
TEMP  -172.75
WGHT    0.017300
FVAR       6.48190
SB1   5    0.721150    0.040767    0.741907    11.00000    0.01197    0.01335 =
         0.01674    0.00080   -0.00092   -0.00135
F5    4    0.600050    0.237334    0.847459    11.00000    0.01504    0.01608 =
         0.02282   -0.00380   -0.00231    0.00039
F6    4    0.992604    0.101819    0.800738    11.00000    0.01184    0.02273 =
         0.03735    0.00057   -0.00358   -0.00436
F7    4    0.745378    0.189320    0.563640    11.00000    0.03546    0.02717 =
         0.01734    0.00663    0.00217    0.00003
F9    4    0.706206   -0.088200    0.933099    11.00000    0.02318    0.02495 =
         0.02478    0.01208    0.00049   -0.00083
F10   4    0.445299   -0.001784    0.696916    11.00000    0.01491    0.02520 =
         0.03561   -0.00451   -0.00803   -0.00373
F8    4    0.846437   -0.145230    0.639942    11.00000    0.02615    0.02256 =
         0.03681   -0.01042    0.00036    0.00397
F3    4    0.133030    0.674238    0.908429    11.00000    0.03648    0.03083 =
         0.02419   -0.00679   -0.00055    0.00304
F1    4   -0.020069    0.483157    0.694414    11.00000    0.02683    0.02338 =
         0.05272    0.00519   -0.02339   -0.00276
F2    4    0.294322    0.436094    0.588514    11.00000    0.05856    0.02791 =
         0.01616   -0.00235    0.00242    0.00158
O1    3    0.223053    0.336282    0.835920    11.00000    0.01402    0.01476 =
         0.02419    0.00535   -0.00264   -0.00198
F4    4    0.456073    0.608734    0.821121    11.00000    0.02073    0.02202 =
         0.04950   -0.00068   -0.00974   -0.00410
C2    1    0.253022    0.639283    0.779525    11.00000    0.02237    0.01707 =
         0.01759    0.00144   -0.00260   -0.00175
C1    1    0.184901    0.473716    0.719247    11.00000    0.02243    0.01775 =
         0.01819    0.00276   -0.00548   -0.00161
H3    2    0.248016    0.726566    0.705263    11.00000    0.02055
H1    2    0.132502    0.256243    0.828993    11.00000    0.05626
H2    2    0.349870    0.304990    0.852323    11.00000    0.05403
HKLF    4




REM  shelxt_a.res in P-1
REM wR2 = 0.0597, GooF = S = 1.081, Restrained GooF = 1.081 for all data
REM R1 = 0.0276 for 2248 Fo > 4sig(Fo) and 0.0349 for all 2548 data
REM 139 parameters refined using 1 restraints

END

WGHT      0.0173      0.0000

REM Highest difference peak  1.199,  deepest hole -1.246,  1-sigma level  0.168
Q1    1   0.8366 -0.1202  0.7693  11.00000  0.05    1.20
Q2    1   0.7398  0.2618  0.7764  11.00000  0.05    0.67
Q3    1   0.7172  0.1020  0.6383  11.00000  0.05    0.66
Q4    1   0.7409 -0.0362  0.8274  11.00000  0.05    0.65
Q5    1   0.8415  0.1135  0.6546  11.00000  0.05    0.59
Q6    1   0.6916  0.3270  0.9015  11.00000  0.05    0.58
Q7    1   0.7075  0.6371  0.8835  11.00000  0.05    0.56
Q8    1   0.0017  0.2245  0.8370  11.00000  0.05    0.55
Q9    1   0.9271 -0.1203  0.8768  11.00000  0.05    0.55
Q10   1   0.6878  0.4402  0.8948  11.00000  0.05    0.55
Q11   1   0.2052  0.4755  0.5261  11.00000  0.05    0.54
Q12   1   0.3309  0.2931  1.0235  11.00000  0.05    0.54
Q13   1   0.0329  0.6072  1.0019  11.00000  0.05    0.53
Q14   1   0.7714  0.3641  0.8425  11.00000  0.05    0.52
Q15   1   0.6363  0.1824  0.5596  11.00000  0.05    0.52
Q16   1   0.1713  0.3031  1.0045  11.00000  0.05    0.52
Q17   1   0.2278  0.4154  0.4349  11.00000  0.05    0.51
Q18   1   0.3591  0.3900  1.0225  11.00000  0.05    0.51
Q19   1   0.0352  0.2107  0.9620  11.00000  0.05    0.51
Q20   1   0.5207  0.5257  0.5662  11.00000  0.05    0.51
;
_shelx_res_checksum              81698

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Anhydrous Hydrogen Fluoride'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Hygroscopic,Heat-sensitive,Oxygen-sensitive
