# 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_240325_1_kageyama_fg_1_0c
_database_code_depnum_ccdc_archive 'CCDC 2463044'
loop_
_audit_author_name
_audit_author_address
'Taichi Nishiguchi'
;Kyoto University
Japan
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-06-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9.999 H11.999 Li N4, F2 N O4 S2'
_chemical_formula_sum            'C10.01 H12.01 F2 Li N5 O4 S2'
_chemical_formula_weight         375.37
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Li C10 H12 N5 O4 S2 F2'
_chemical_oxdiff_usercomment     0degC
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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.8522(6)
_cell_length_b                   12.8465(6)
_cell_length_c                   5.2547(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     867.59(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3207
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      19.9950
_cell_measurement_theta_min      2.3430
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            14670
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.750
_diffrn_reflns_theta_min         3.170
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -77.00   0.50    2.13    --  -18.00  45.00 174.03   60
  2  ω    -68.00 -41.00   0.50    2.13    --  -18.00  45.00  60.00   54
  3  ω    -36.00 -11.00   0.50    2.13    --  -18.00  45.00  60.00   50
  4  ω     -9.00  70.00   0.50    2.13    --  -18.00  45.00  60.00  158
  5  ω   -107.00  65.00   0.50    2.13    --  -18.00  45.00 120.00  344
  6  ω    -10.00  15.00   0.50    2.13    --  -18.00  45.00  30.00   50
  7  ω   -107.00 -81.00   0.50    2.13    --  -18.00  45.00 -17.49   52
  8  ω     14.00  71.00   0.50    2.13    --  -18.00  45.00 -17.49  114
  9  ω   -106.00  70.00   0.50    2.13    --  -18.00  45.00 179.90  352
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0268903000
_diffrn_orient_matrix_UB_12      -0.0037799000
_diffrn_orient_matrix_UB_13      -0.1174702000
_diffrn_orient_matrix_UB_21      0.0467782000
_diffrn_orient_matrix_UB_22      -0.0111949000
_diffrn_orient_matrix_UB_23      0.0661606000
_diffrn_orient_matrix_UB_31      -0.0116345000
_diffrn_orient_matrix_UB_32      -0.0539488000
_diffrn_orient_matrix_UB_33      -0.0054457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                1154
_reflns_number_total             2719
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.092
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     440
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.080
_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)+(0.0455P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0995
_refine_special_details          
;
 Refined as a 4-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(6)
 0.37(8) 0(6) 0.13(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
3. Restrained distances
 N1-C1 = N2-C5 = N1A-C1A = N2A-C5A = N1B-C1B
 1.136 with sigma of 0.02
 N3-S1 = N3-S2
 1.642 with sigma of 0.02
 S1-F1 = S2-F2
 1.527 with sigma of 0.02
 C1-C2 = C4-C5 = C1A-C2A = C4A-C5A = C1B-C2B = C4B-C5B
 1.47 with sigma of 0.02
 C2-C3 = C3-C4 = C2A-C3A = C3A-C4A = C2B-C3B = C3B-C4B
 1.524 with sigma of 0.02
 S1-O1 = S1-O2 = S2-O3 = S2-O4
 1.428 with sigma of 0.02
 S1-S2
 2.844 with sigma of 0.04
 N1-C2 = N2-C4 = N1A-C2A = N2A-C4A = N1B-C2B
 2.606 with sigma of 0.04
 N3-F1 = N3-F2
 2.589 with sigma of 0.04
 C1-C3 = C3-C5 = C1A-C3A = C3A-C5A = C1B-C3B = C3B-C5B
 2.445 with sigma of 0.04
 C2-C4 = C2A-C4A = C2B-C4B
 2.489 with sigma of 0.04
 N3-O1 = N3-O2 = N3-O3 = N3-O4
 2.51 with sigma of 0.04
 F1-O1 = F1-O2 = F2-O3 = F2-O4
 2.414 with sigma of 0.04
 O1-O2 = O3-O4
 2.332 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 2A
N1A \\sim N2A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
N1B \\sim N2B \\sim C1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(N3) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(S2) \\sim Ueq, Uanis(O1) \\sim
Ueq, Uanis(O2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms
of 0.04
Uanis(N1) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(N1A)
\\sim Ueq, Uanis(N2A) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq,
Uanis(C3A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(N1B)
\\sim Ueq, Uanis(N2B) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C2B) \\sim Ueq,
Uanis(C3B) \\sim Ueq, Uanis(C4B) \\sim Ueq, Uanis(C5B) \\sim Ueq: with sigma of
0.02 and sigma for terminal atoms of 0.04
5. Rigid body (RIGU) restrains
 N1, N2, C1, C2, C3, C4, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1A, N2A, C1A, C2A, C3A, C4A, C5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1B, N2B, C1B, C2B, C3B, C4B, C5B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 1*[Sof(N1)+Sof(N2)+Sof(C1)+Sof(C2)+Sof(H2A)+Sof(H2B)+Sof(C3)+Sof(H3A)+
 Sof(H3B)+Sof(C4)+Sof(H4A)+Sof(H4B)+Sof(C5)]+1*[Sof(N1A)+Sof(N2A)+Sof(C1A)+
 Sof(C2A)+Sof(H2AA)+Sof(H2AB)+Sof(C3A)+Sof(H3AA)+Sof(H3AB)+Sof(C4A)+Sof(H4AA)+
 Sof(H4AB)+Sof(C5A)]+1*[Sof(N1B)+Sof(N2B)+Sof(C1B)+Sof(C2B)+Sof(H2BA)+Sof(H2BB)+
 Sof(C3B)+Sof(H3BA)+Sof(H3BB)+Sof(C4B)+Sof(H4BA)+Sof(H4BB)+Sof(C5B)]=1 with esd
 of 0.001
 Sof(N1)=Sof(N2)=Sof(C1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=FVAR(1)
 Sof(N1A)=Sof(N2A)=Sof(C1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=
 Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=FVAR(2)
 Sof(N1B)=Sof(N2B)=Sof(C1B)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C3B)=Sof(H3BA)=
 Sof(H3BB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=FVAR(3)
 Fixed Sof: S1(0.5) S2(0.5) F1(0.5) F2(0.5) O1(0.5) O2(0.5) O3(0.5) O4(0.5)
 N3(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C2A(H2AA,H2AB), C3A(H3AA,H3AB),
 C4A(H4AA,H4AB), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C4B(H4BA,H4BB)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.623(2) 0.447(2) 0.824(6) 0.178(9) Uani 0.464(15) 1 d D U P A 1
N2 N 0.913(2) 0.1107(19) 0.742(5) 0.155(8) Uani 0.464(15) 1 d D U P A 1
C1 C 0.691(2) 0.410(2) 0.719(6) 0.174(9) Uani 0.464(15) 1 d D U P A 1
C2 C 0.7832(19) 0.355(2) 0.598(6) 0.200(8) Uani 0.464(15) 1 d D U P A 1
H2A H 0.825148 0.404355 0.501972 0.240 Uiso 0.464(15) 1 calc R U P A 1
H2B H 0.826481 0.323187 0.727120 0.240 Uiso 0.464(15) 1 calc R U P A 1
C3 C 0.7387(18) 0.2772(14) 0.431(4) 0.184(7) Uani 0.464(15) 1 d D U P A 1
H3A H 0.708084 0.309420 0.281883 0.221 Uiso 0.464(15) 1 calc R U P A 1
H3B H 0.685392 0.237648 0.518999 0.221 Uiso 0.464(15) 1 calc R U P A 1
C4 C 0.827(2) 0.2085(16) 0.358(4) 0.176(7) Uani 0.464(15) 1 d D U P A 1
H4A H 0.880683 0.250305 0.276055 0.211 Uiso 0.464(15) 1 calc R U P A 1
H4B H 0.803203 0.157619 0.234617 0.211 Uiso 0.464(15) 1 calc R U P A 1
C5 C 0.8743(18) 0.1526(11) 0.580(4) 0.133(5) Uani 0.464(15) 1 d D U P A 1
Li1 Li 0.500000 0.500000 1.031(5) 0.177(6) Uani 1 2 d S T P . .
N1A N 0.588(2) 0.414(3) 0.721(6) 0.128(9) Uani 0.273(13) 1 d D U P A 2
N2A N 0.930(4) 0.103(3) 0.828(8) 0.145(11) Uani 0.273(13) 1 d D U P A 2
C1A C 0.641(2) 0.3871(19) 0.557(5) 0.117(6) Uani 0.273(13) 1 d D U P A 2
C2A C 0.7096(18) 0.3443(14) 0.361(4) 0.112(6) Uani 0.273(13) 1 d D U P A 2
H2AA H 0.758297 0.397930 0.308832 0.134 Uiso 0.273(13) 1 calc R U P A 2
H2AB H 0.668166 0.325838 0.213213 0.134 Uiso 0.273(13) 1 calc R U P A 2
C3A C 0.7697(12) 0.2506(14) 0.444(3) 0.088(4) Uani 0.273(13) 1 d D U P A 2
H3AA H 0.803190 0.219333 0.297672 0.106 Uiso 0.273(13) 1 calc R U P A 2
H3AB H 0.721979 0.199712 0.515215 0.106 Uiso 0.273(13) 1 calc R U P A 2
C4A C 0.8511(16) 0.2771(11) 0.641(4) 0.107(6) Uani 0.273(13) 1 d D U P A 2
H4AA H 0.817743 0.310588 0.784420 0.128 Uiso 0.273(13) 1 calc R U P A 2
H4AB H 0.899989 0.326238 0.567514 0.128 Uiso 0.273(13) 1 calc R U P A 2
C5A C 0.910(2) 0.1828(16) 0.734(5) 0.107(6) Uani 0.273(13) 1 d D U P A 2
N1B N 0.591(3) 0.438(3) 0.783(7) 0.125(9) Uani 0.263(14) 1 d D U P A 3
N2B N 0.9675(16) 0.113(2) 0.759(6) 0.112(6) Uani 0.263(14) 1 d . U P A 3
C1B C 0.654(3) 0.399(4) 0.658(8) 0.141(12) Uani 0.263(14) 1 d D U P A 3
C2B C 0.738(3) 0.362(3) 0.473(6) 0.151(9) Uani 0.263(14) 1 d D U P A 3
H2BA H 0.706915 0.336444 0.315923 0.181 Uiso 0.263(14) 1 calc R U P A 3
H2BB H 0.786222 0.417147 0.433498 0.181 Uiso 0.263(14) 1 calc R U P A 3
C3B C 0.791(2) 0.2749(19) 0.615(5) 0.137(7) Uani 0.263(14) 1 d D U P A 3
H3BA H 0.737737 0.229887 0.688053 0.165 Uiso 0.263(14) 1 calc R U P A 3
H3BB H 0.830109 0.304579 0.754737 0.165 Uiso 0.263(14) 1 calc R U P A 3
C4B C 0.864(2) 0.209(2) 0.451(6) 0.137(7) Uani 0.263(14) 1 d D U P A 3
H4BA H 0.824158 0.168178 0.329003 0.165 Uiso 0.263(14) 1 calc R U P A 3
H4BB H 0.911753 0.253274 0.358185 0.165 Uiso 0.263(14) 1 calc R U P A 3
C5B C 0.9208(18) 0.140(3) 0.631(6) 0.107(6) Uani 0.263(14) 1 d D U P A 3
S1 S 0.0708(6) 0.4258(5) 1.0060(14) 0.154(3) Uani 0.5 1 d D U P B -1
S2 S -0.0797(10) 0.5735(6) 1.029(2) 0.191(5) Uani 0.5 1 d D U P B -1
F1 F 0.0717(17) 0.4242(15) 0.7250(16) 0.241(7) Uani 0.5 1 d D U P B -1
F2 F -0.1320(16) 0.545(2) 0.791(4) 0.295(9) Uani 0.5 1 d D U P B -1
O1 O 0.0097(13) 0.3515(8) 1.110(4) 0.245(8) Uani 0.5 1 d D U P B -1
O2 O 0.1785(15) 0.444(2) 1.042(5) 0.289(12) Uani 0.5 1 d D U P B -1
O3 O -0.1329(19) 0.5414(19) 1.247(4) 0.313(12) Uani 0.5 1 d D U P B -1
O4 O -0.0951(16) 0.6792(9) 1.083(3) 0.282(11) Uani 0.5 1 d D U P B -1
N3 N 0.0381(13) 0.5418(6) 1.0636(15) 0.177(4) Uani 0.5 1 d D U P B -1


_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
N1 C1 1.13(2) . ?
N1 Li1 2.04(3) . ?
N2 C5 1.123(17) . ?
N2 Li1 2.17(2) 3_557 ?
C1 C2 1.52(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.45(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.49(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.497(19) . ?
Li1 N1A 2.27(3) . ?
Li1 N1A 2.27(3) 2_665 ?
Li1 N2A 1.77(3) 4_657 ?
Li1 N2A 1.77(3) 3_457 ?
Li1 N1B 1.92(3) . ?
Li1 N1B 1.92(3) 2_665 ?
Li1 N2B 1.88(4) 3_457 ?
Li1 N2B 1.88(4) 4_657 ?
N1A C1A 1.15(2) . ?
N2A C5A 1.17(2) . ?
C1A C2A 1.47(2) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.497(19) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A C4A 1.508(17) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.509(18) . ?
N1B C1B 1.16(2) . ?
N2B C5B 0.96(4) . ?
C1B C2B 1.53(2) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C2B C3B 1.50(2) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C3B C4B 1.53(2) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4B C5B 1.49(2) . ?
S1 F1 1.476(10) . ?
S1 O1 1.353(13) . ?
S1 O2 1.417(17) . ?
S1 N3 1.577(12) . ?
S2 F2 1.467(18) . ?
S2 O3 1.397(15) . ?
S2 O4 1.402(12) . ?
S2 N3 1.579(15) . ?

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
C1 N1 Li1 175(3) . . ?
C5 N2 Li1 164(2) . 3_557 ?
N1 C1 C2 175(4) . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 C1 105.5(19) . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C2 C3 C4 105.4(19) . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C3 C4 C5 112.9(18) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
N2 C5 C4 178(2) . . ?
N1 Li1 N1 116(2) 2_665 . ?
N1 Li1 N2 96.4(12) . 4_657 ?
N1 Li1 N2 118.4(12) 2_665 4_657 ?
N1 Li1 N2 96.4(12) 2_665 3_457 ?
N1 Li1 N2 118.4(12) . 3_457 ?
N1 Li1 N1A 99.7(17) . 2_665 ?
N1 Li1 N1A 21.3(13) 2_665 2_665 ?
N2 Li1 N2 113.1(19) 4_657 3_457 ?
N2 Li1 N1A 109.3(12) 4_657 2_665 ?
N2 Li1 N1A 117.3(13) 3_457 2_665 ?
N2A Li1 N1A 114.4(18) 4_657 . ?
N2A Li1 N1A 100.9(19) 3_457 . ?
N1B Li1 N1B 94(3) 2_665 . ?
N2B Li1 N1B 125.9(13) 4_657 . ?
N2B Li1 N1B 102.4(13) 3_457 . ?
C1A N1A Li1 167(3) . . ?
N1A C1A C2A 175(2) . . ?
C1A C2A H2AA 108.7 . . ?
C1A C2A H2AB 108.7 . . ?
C1A C2A C3A 114.1(16) . . ?
H2AA C2A H2AB 107.6 . . ?
C3A C2A H2AA 108.7 . . ?
C3A C2A H2AB 108.7 . . ?
C2A C3A H3AA 109.2 . . ?
C2A C3A H3AB 109.2 . . ?
C2A C3A C4A 112.2(15) . . ?
H3AA C3A H3AB 107.9 . . ?
C4A C3A H3AA 109.2 . . ?
C4A C3A H3AB 109.2 . . ?
C3A C4A H4AA 109.0 . . ?
C3A C4A H4AB 109.0 . . ?
C3A C4A C5A 112.9(14) . . ?
H4AA C4A H4AB 107.8 . . ?
C5A C4A H4AA 109.0 . . ?
C5A C4A H4AB 109.0 . . ?
N2A C5A C4A 162(4) . . ?
C1B N1B Li1 171(4) . . ?
N1B C1B C2B 172(5) . . ?
C1B C2B H2BA 111.1 . . ?
C1B C2B H2BB 111.1 . . ?
H2BA C2B H2BB 109.0 . . ?
C3B C2B C1B 104(2) . . ?
C3B C2B H2BA 111.1 . . ?
C3B C2B H2BB 111.1 . . ?
C2B C3B H3BA 108.8 . . ?
C2B C3B H3BB 108.8 . . ?
C2B C3B C4B 114(2) . . ?
H3BA C3B H3BB 107.7 . . ?
C4B C3B H3BA 108.8 . . ?
C4B C3B H3BB 108.8 . . ?
C3B C4B H4BA 110.6 . . ?
C3B C4B H4BB 110.6 . . ?
H4BA C4B H4BB 108.7 . . ?
C5B C4B C3B 106(2) . . ?
C5B C4B H4BA 110.6 . . ?
C5B C4B H4BB 110.6 . . ?
N2B C5B C4B 164(4) . . ?
F1 S1 N3 102.0(7) . . ?
O1 S1 F1 113.5(17) . . ?
O1 S1 O2 129.1(13) . . ?
O1 S1 N3 115.7(8) . . ?
O2 S1 F1 97.5(14) . . ?
O2 S1 N3 94.4(14) . . ?
F2 S2 N3 118.2(11) . . ?
O3 S2 F2 113.5(15) . . ?
O3 S2 O4 92.9(13) . . ?
O3 S2 N3 107.4(13) . . ?
O4 S2 F2 110.6(14) . . ?
O4 S2 N3 111.3(11) . . ?
S1 N3 S2 118.5(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -168(2) . . . . ?
C2 C3 C4 C5 63(3) . . . . ?
Li1 N2A C5A C4A -160(8) 3_557 . . . ?
Li1 N2B C5B C4B 168(7) 3_557 . . . ?
C1A C2A C3A C4A -69(3) . . . . ?
C2A C3A C4A C5A 178(2) . . . . ?
C3A C4A C5A N2A -63(9) . . . . ?
C1B C2B C3B C4B 168(3) . . . . ?
C2B C3B C4B C5B 171(3) . . . . ?
C3B C4B C5B N2B -73(10) . . . . ?
F1 S1 N3 S2 76.3(13) . . . . ?
F2 S2 N3 S1 -49.2(15) . . . . ?
O1 S1 N3 S2 -47.4(11) . . . . ?
O2 S1 N3 S2 174.9(13) . . . . ?
O3 S2 N3 S1 80.8(13) . . . . ?
O4 S2 N3 S1 -178.9(10) . . . . ?

_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 1.608
_oxdiff_exptl_absorpt_empirical_full_min 0.774
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(6)
2 0.37(8)
3 0(6)
4 0.13(8)

####################################################################### 
# 
# 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_li(tfsi)(bpe)2_auto
_database_code_depnum_ccdc_archive 'CCDC 2480466'
loop_
_audit_author_name
_audit_author_address
'Taichi Nishiguchi'
;Kyoto University
Japan
;
_audit_update_record             
;
2025-08-14 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-07-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 F6 N O4 S2, C24 H24 Li N4'
_chemical_formula_sum            'C26 H24 F6 Li N5 O4 S2'
_chemical_formula_weight         655.56
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'H, Li, C, N, O, F, S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      tetragonal
_space_group_IT_number           81
_space_group_name_H-M_alt        'P -4'
_space_group_name_Hall           'P -4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'

_cell_length_a                   21.30250(10)
_cell_length_b                   21.30250(10)
_cell_length_c                   6.45130(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2927.58(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13272
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7630
_cell_measurement_theta_min      2.9280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            17018
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.899
_diffrn_reflns_theta_min         2.934
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00  75.00   0.50    0.06    --  107.00 -61.00-180.00   52
  2  ω     35.00  75.00   0.50    0.06    --  107.00 -61.00 -60.00   80
  3  ω    -23.00  44.00   0.50    0.05    --   48.70 -36.00 -39.00  134
  4  ω    -24.00  30.00   0.50    0.05    --   48.70 -19.00-180.00  108
  5  ω     46.00  73.00   0.50    0.06    --  107.00 -61.00 150.00   54
  6  ω     99.00 178.00   0.50    0.06    --  107.00  36.00 116.00  158
  7  ω     37.00 106.00   0.50    0.06    --  107.00-102.00 112.00  138
  8  ω     40.00  88.00   0.50    0.06    --  107.00-125.00  30.00   96
  9  ω     38.00 109.00   0.50    0.06    --  107.00-125.00-120.00  142
 10  ω     38.00 112.00   0.50    0.06    --  107.00-125.00-180.00  148
 11  ω    -81.00  14.00   0.50    0.05    --  -48.70 102.00-144.00  190
 12  ω    -68.00 -32.00   0.50    0.06    -- -104.50  61.00-180.00   72
 13  ω   -101.00 -32.00   0.50    0.06    -- -104.50  77.00  60.00  138
 14  ω    -68.00 -32.00   0.50    0.06    -- -104.50  61.00 120.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0664824000
_diffrn_orient_matrix_UB_12      0.0112988000
_diffrn_orient_matrix_UB_13      -0.0865499000
_diffrn_orient_matrix_UB_21      -0.0194002000
_diffrn_orient_matrix_UB_22      0.0665460000
_diffrn_orient_matrix_UB_23      -0.0679704000
_diffrn_orient_matrix_UB_31      0.0208972000
_diffrn_orient_matrix_UB_32      0.0259182000
_diffrn_orient_matrix_UB_33      0.2119081000
_diffrn_oxdiff_digest_hkl        
;
01349244cc952b7765f1da92e176124db93140
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                5614
_reflns_number_total             5891
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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         0.231
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 2326 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(7)
_refine_ls_extinction_coef       0.00049(11)
_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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5891
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.044
_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)+(0.0444P)²+0.1618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0716
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C37(H37A,H37B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 C39(H39), C29(H29), C42(H42), C17(H17), C28(H28), C25(H25), C43(H43),
 C31(H31), C26(H26), C40(H40), C20(H20), C21(H21), C18(H18), C35(H35), C34(H34),
  C32(H32)
;
_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
S1 S 0.75674(2) 0.18650(2) 1.36570(7) 0.02040(12) Uani 1 1 d . . . . .
S3 S 0.74579(2) 0.31728(2) 1.35468(8) 0.02054(12) Uani 1 1 d . . . . .
F12 F 0.69038(7) 0.20288(7) 1.7028(2) 0.0367(3) Uani 1 1 d . . . . .
F11 F 0.78722(7) 0.17883(7) 1.7593(2) 0.0367(3) Uani 1 1 d . . . . .
F13 F 0.72250(8) 0.10821(7) 1.6540(2) 0.0378(3) Uani 1 1 d . . . . .
F5 F 0.73391(8) 0.39283(7) 1.0402(3) 0.0417(4) Uani 1 1 d . . . . .
F7 F 0.81939(8) 0.33842(8) 1.0365(3) 0.0429(4) Uani 1 1 d . . . . .
O8 O 0.67939(7) 0.31228(8) 1.3745(3) 0.0297(4) Uani 1 1 d . . . . .
F6 F 0.73123(9) 0.29500(8) 0.9584(2) 0.0459(4) Uani 1 1 d . . . . .
O9 O 0.77783(9) 0.36645(8) 1.4624(3) 0.0334(4) Uani 1 1 d . . . . .
O15 O 0.69853(9) 0.18003(8) 1.2590(3) 0.0323(4) Uani 1 1 d . . . . .
O14 O 0.80626(9) 0.14375(8) 1.3187(3) 0.0346(4) Uani 1 1 d . . . . .
N24 N 0.51589(8) 0.07714(8) 0.9406(3) 0.0189(3) Uani 1 1 d . . . . .
N38 N 0.42509(8) 0.01665(8) 0.5721(3) 0.0183(3) Uani 1 1 d . . . . .
N30 N 0.07796(8) 0.00393(9) -0.3153(3) 0.0206(4) Uani 1 1 d . . . . .
N16 N 0.51930(8) 0.42434(8) 1.8201(3) 0.0203(4) Uani 1 1 d . . . . .
N2 N 0.78488(8) 0.25481(8) 1.3804(3) 0.0230(4) Uani 1 1 d . . . . .
C39 C 0.38669(10) 0.06651(10) 0.5789(3) 0.0206(4) Uani 1 1 d . . . . .
H39 H 0.398160 0.100728 0.665391 0.025 Uiso 1 1 calc R U . . .
C29 C 0.56552(10) 0.11577(10) 0.9186(3) 0.0208(4) Uani 1 1 d . . . . .
H29 H 0.598442 0.103310 0.828215 0.025 Uiso 1 1 calc R U . . .
C42 C 0.35304(10) -0.03064(10) 0.3313(3) 0.0213(4) Uani 1 1 d . . . . .
H42 H 0.342843 -0.065540 0.246056 0.026 Uiso 1 1 calc R U . . .
C17 C 0.47290(10) 0.40327(10) 1.6968(3) 0.0211(4) Uani 1 1 d . . . . .
H17 H 0.436509 0.428619 1.681420 0.025 Uiso 1 1 calc R U . . .
C28 C 0.57108(10) 0.17247(10) 1.0204(3) 0.0204(4) Uani 1 1 d . . . . .
H28 H 0.607251 0.197836 1.000369 0.025 Uiso 1 1 calc R U . . .
C41 C 0.31277(10) 0.02108(10) 0.3422(3) 0.0201(4) Uani 1 1 d . . . . .
C27 C 0.52339(10) 0.19228(9) 1.1526(3) 0.0190(4) Uani 1 1 d . . . . .
C25 C 0.47049(10) 0.09603(10) 1.0707(3) 0.0203(4) Uani 1 1 d . . . . .
H25 H 0.435184 0.069412 1.089884 0.024 Uiso 1 1 calc R U . . .
C43 C 0.40782(10) -0.03044(10) 0.4458(3) 0.0197(4) Uani 1 1 d . . . . .
H43 H 0.434897 -0.065707 0.434691 0.024 Uiso 1 1 calc R U . . .
C31 C 0.12089(10) 0.04948(10) -0.3358(3) 0.0234(4) Uani 1 1 d . . . . .
H31 H 0.111694 0.083675 -0.425268 0.028 Uiso 1 1 calc R U . . .
C26 C 0.47231(10) 0.15219(10) 1.1783(3) 0.0207(4) Uani 1 1 d . . . . .
H26 H 0.439001 0.163313 1.269114 0.025 Uiso 1 1 calc R U . . .
C40 C 0.33145(10) 0.07107(10) 0.4676(3) 0.0203(4) Uani 1 1 d . . . . .
H40 H 0.306428 0.107888 0.476426 0.024 Uiso 1 1 calc R U . . .
C20 C 0.57694(10) 0.33097(10) 1.7330(3) 0.0213(4) Uani 1 1 d . . . . .
H20 H 0.614382 0.307160 1.747721 0.026 Uiso 1 1 calc R U . . .
C22 C 0.53195(11) 0.24676(10) 1.4985(3) 0.0217(4) Uani 1 1 d . . . . .
H22A H 0.497707 0.219155 1.548053 0.026 Uiso 1 1 calc R U . . .
H22B H 0.572378 0.226252 1.532296 0.026 Uiso 1 1 calc R U . . .
C21 C 0.57038(10) 0.38785(10) 1.8342(3) 0.0214(4) Uani 1 1 d . . . . .
H21 H 0.604090 0.401885 1.918763 0.026 Uiso 1 1 calc R U . . .
C18 C 0.47515(10) 0.34697(10) 1.5915(3) 0.0203(4) Uani 1 1 d . . . . .
H18 H 0.440860 0.334160 1.507410 0.024 Uiso 1 1 calc R U . . .
C19 C 0.52818(10) 0.30900(9) 1.6095(3) 0.0190(4) Uani 1 1 d . . . . .
C35 C 0.09180(11) -0.04273(11) -0.1832(3) 0.0245(4) Uani 1 1 d . . . . .
H35 H 0.061462 -0.074820 -0.162662 0.029 Uiso 1 1 calc R U . . .
C23 C 0.52666(12) 0.25448(10) 1.2632(3) 0.0240(4) Uani 1 1 d . . . . .
H23A H 0.488533 0.279144 1.230563 0.029 Uiso 1 1 calc R U . . .
H23B H 0.563450 0.278250 1.211889 0.029 Uiso 1 1 calc R U . . .
C34 C 0.14747(12) -0.04668(12) -0.0759(3) 0.0278(5) Uani 1 1 d . . . . .
H34 H 0.155022 -0.080879 0.015238 0.033 Uiso 1 1 calc R U . . .
C32 C 0.17796(11) 0.04924(12) -0.2331(3) 0.0272(5) Uani 1 1 d . . . . .
H32 H 0.206838 0.082722 -0.252456 0.033 Uiso 1 1 calc R U . . .
C37 C 0.25092(11) 0.02245(11) 0.2283(4) 0.0259(5) Uani 1 1 d . . . . .
H37A H 0.235721 0.066322 0.222159 0.031 Uiso 1 1 calc R U . . .
H37B H 0.219777 -0.002304 0.307613 0.031 Uiso 1 1 calc R U . . .
C33 C 0.19269(11) -0.00007(13) -0.1021(3) 0.0280(5) Uani 1 1 d . . . . .
C10 C 0.73841(11) 0.16832(11) 1.6369(3) 0.0260(4) Uani 1 1 d . . . . .
C4 C 0.75862(12) 0.33679(11) 1.0815(4) 0.0290(5) Uani 1 1 d . . . . .
C36 C 0.25475(12) -0.00347(16) 0.0092(4) 0.0384(6) Uani 1 1 d . . . . .
H36A H 0.286459 0.020620 -0.069940 0.046 Uiso 1 1 calc R U . . .
H36B H 0.268773 -0.047740 0.014839 0.046 Uiso 1 1 calc R U . . .
Li44 Li 0.500000 0.500000 2.000000 0.0191(13) Uani 1 4 d S T P . .
Li45 Li 0.000000 0.000000 -0.500000 0.0183(13) Uani 1 4 d S T P . .
Li46 Li 0.500000 0.000000 0.7616(7) 0.0187(9) Uani 1 2 d S T P . .


_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 O15 1.4248(17) . ?
S1 O14 1.4263(18) . ?
S1 N2 1.5766(18) . ?
S1 C10 1.834(2) . ?
S3 O8 1.4243(16) . ?
S3 O9 1.4303(17) . ?
S3 N2 1.5787(18) . ?
S3 C4 1.831(2) . ?
F12 C10 1.330(3) . ?
F11 C10 1.325(3) . ?
F13 C10 1.329(3) . ?
F5 C4 1.332(3) . ?
F7 C4 1.327(3) . ?
F6 C4 1.328(3) . ?
N24 C29 1.347(3) . ?
N24 C25 1.342(3) . ?
N24 Li46 2.037(3) . ?
N38 C39 1.341(3) . ?
N38 C43 1.343(3) . ?
N38 Li46 2.042(3) . ?
N30 C31 1.340(3) . ?
N30 C35 1.342(3) . ?
N30 Li45 2.0456(17) . ?
N16 C17 1.346(3) . ?
N16 C21 1.340(3) . ?
N16 Li44 2.0284(18) . ?
C39 H39 0.9500 . ?
C39 C40 1.382(3) . ?
C29 H29 0.9500 . ?
C29 C28 1.380(3) . ?
C42 H42 0.9500 . ?
C42 C41 1.398(3) . ?
C42 C43 1.381(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(3) . ?
C28 H28 0.9500 . ?
C28 C27 1.392(3) . ?
C41 C40 1.395(3) . ?
C41 C37 1.509(3) . ?
C27 C26 1.393(3) . ?
C27 C23 1.507(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.384(3) . ?
C43 H43 0.9500 . ?
C31 H31 0.9500 . ?
C31 C32 1.384(3) . ?
C26 H26 0.9500 . ?
C40 H40 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.384(3) . ?
C20 C19 1.390(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C19 1.509(3) . ?
C22 C23 1.531(3) . ?
C21 H21 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.394(3) . ?
C35 H35 0.9500 . ?
C35 C34 1.376(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C34 H34 0.9500 . ?
C34 C33 1.394(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.384(4) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C36 1.520(3) . ?
C33 C36 1.506(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

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
O15 S1 O14 118.63(11) . . ?
O15 S1 N2 116.70(10) . . ?
O15 S1 C10 104.78(11) . . ?
O14 S1 N2 108.71(10) . . ?
O14 S1 C10 103.03(11) . . ?
N2 S1 C10 102.62(10) . . ?
O8 S3 O9 119.01(11) . . ?
O8 S3 N2 116.82(10) . . ?
O8 S3 C4 104.58(11) . . ?
O9 S3 N2 108.34(10) . . ?
O9 S3 C4 103.30(11) . . ?
N2 S3 C4 102.35(11) . . ?
C29 N24 Li46 124.30(16) . . ?
C25 N24 C29 116.63(18) . . ?
C25 N24 Li46 118.47(15) . . ?
C39 N38 C43 116.36(17) . . ?
C39 N38 Li46 126.48(15) . . ?
C43 N38 Li46 116.59(14) . . ?
C31 N30 C35 116.68(19) . . ?
C31 N30 Li45 121.76(14) . . ?
C35 N30 Li45 121.19(15) . . ?
C17 N16 Li44 117.03(14) . . ?
C21 N16 C17 116.30(18) . . ?
C21 N16 Li44 125.90(14) . . ?
S1 N2 S3 124.83(12) . . ?
N38 C39 H39 118.0 . . ?
N38 C39 C40 123.91(19) . . ?
C40 C39 H39 118.0 . . ?
N24 C29 H29 118.3 . . ?
N24 C29 C28 123.50(19) . . ?
C28 C29 H29 118.3 . . ?
C41 C42 H42 120.4 . . ?
C43 C42 H42 120.4 . . ?
C43 C42 C41 119.29(19) . . ?
N16 C17 H17 118.1 . . ?
N16 C17 C18 123.7(2) . . ?
C18 C17 H17 118.1 . . ?
C29 C28 H28 120.2 . . ?
C29 C28 C27 119.6(2) . . ?
C27 C28 H28 120.2 . . ?
C42 C41 C37 121.78(19) . . ?
C40 C41 C42 117.09(19) . . ?
C40 C41 C37 121.12(19) . . ?
C28 C27 C26 117.21(19) . . ?
C28 C27 C23 121.55(19) . . ?
C26 C27 C23 121.24(19) . . ?
N24 C25 H25 118.2 . . ?
N24 C25 C26 123.56(19) . . ?
C26 C25 H25 118.2 . . ?
N38 C43 C42 123.93(19) . . ?
N38 C43 H43 118.0 . . ?
C42 C43 H43 118.0 . . ?
N30 C31 H31 118.3 . . ?
N30 C31 C32 123.3(2) . . ?
C32 C31 H31 118.3 . . ?
C27 C26 H26 120.3 . . ?
C25 C26 C27 119.46(19) . . ?
C25 C26 H26 120.3 . . ?
C39 C40 C41 119.37(19) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
C21 C20 H20 120.3 . . ?
C21 C20 C19 119.3(2) . . ?
C19 C20 H20 120.3 . . ?
H22A C22 H22B 107.9 . . ?
C19 C22 H22A 109.2 . . ?
C19 C22 H22B 109.2 . . ?
C19 C22 C23 111.86(18) . . ?
C23 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
N16 C21 C20 123.9(2) . . ?
N16 C21 H21 118.1 . . ?
C20 C21 H21 118.1 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.4(2) . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C22 121.87(19) . . ?
C20 C19 C18 117.26(19) . . ?
C18 C19 C22 120.88(19) . . ?
N30 C35 H35 118.2 . . ?
N30 C35 C34 123.7(2) . . ?
C34 C35 H35 118.2 . . ?
C27 C23 C22 112.26(18) . . ?
C27 C23 H23A 109.2 . . ?
C27 C23 H23B 109.2 . . ?
C22 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C35 C34 H34 120.3 . . ?
C35 C34 C33 119.4(2) . . ?
C33 C34 H34 120.3 . . ?
C31 C32 H32 120.2 . . ?
C33 C32 C31 119.6(2) . . ?
C33 C32 H32 120.2 . . ?
C41 C37 H37A 108.9 . . ?
C41 C37 H37B 108.9 . . ?
C41 C37 C36 113.52(19) . . ?
H37A C37 H37B 107.7 . . ?
C36 C37 H37A 108.9 . . ?
C36 C37 H37B 108.9 . . ?
C34 C33 C36 121.0(2) . . ?
C32 C33 C34 117.3(2) . . ?
C32 C33 C36 121.8(2) . . ?
F12 C10 S1 110.59(15) . . ?
F11 C10 S1 111.46(16) . . ?
F11 C10 F12 108.63(19) . . ?
F11 C10 F13 108.26(19) . . ?
F13 C10 S1 109.70(16) . . ?
F13 C10 F12 108.10(19) . . ?
F5 C4 S3 109.70(17) . . ?
F7 C4 S3 111.23(17) . . ?
F7 C4 F5 108.55(19) . . ?
F7 C4 F6 108.4(2) . . ?
F6 C4 S3 110.96(16) . . ?
F6 C4 F5 107.9(2) . . ?
C37 C36 H36A 109.1 . . ?
C37 C36 H36B 109.1 . . ?
C33 C36 C37 112.3(2) . . ?
C33 C36 H36A 109.1 . . ?
C33 C36 H36B 109.1 . . ?
H36A C36 H36B 107.9 . . ?
N16 Li44 N16 110.18(10) 4_659 3_569 ?
N16 Li44 N16 109.12(5) 3_569 . ?
N16 Li44 N16 109.12(5) 4_659 . ?
N16 Li44 N16 109.12(5) 4_659 2_665 ?
N16 Li44 N16 109.12(5) 3_569 2_665 ?
N16 Li44 N16 110.18(10) 2_665 . ?
N30 Li45 N30 109.83(5) 3_554 2 ?
N30 Li45 N30 109.83(5) 4_554 . ?
N30 Li45 N30 108.75(10) 2 . ?
N30 Li45 N30 108.75(10) 3_554 4_554 ?
N30 Li45 N30 109.83(5) 3_554 . ?
N30 Li45 N30 109.83(5) 2 4_554 ?
N24 Li46 N24 110.9(2) 2_655 . ?
N24 Li46 N38 109.23(7) 2_655 2_655 ?
N24 Li46 N38 110.48(7) . 2_655 ?
N24 Li46 N38 110.48(7) 2_655 . ?
N24 Li46 N38 109.23(7) . . ?
N38 Li46 N38 106.4(2) . 2_655 ?

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
O8 S3 N2 S1 17.4(2) . . . . ?
O8 S3 C4 F5 64.50(19) . . . . ?
O8 S3 C4 F7 -175.39(16) . . . . ?
O8 S3 C4 F6 -54.7(2) . . . . ?
O9 S3 N2 S1 155.14(14) . . . . ?
O9 S3 C4 F5 -60.70(19) . . . . ?
O9 S3 C4 F7 59.41(19) . . . . ?
O9 S3 C4 F6 -179.86(18) . . . . ?
O15 S1 N2 S3 20.9(2) . . . . ?
O15 S1 C10 F12 -52.50(18) . . . . ?
O15 S1 C10 F11 -173.46(16) . . . . ?
O15 S1 C10 F13 66.65(18) . . . . ?
O14 S1 N2 S3 158.38(14) . . . . ?
O14 S1 C10 F12 -177.23(16) . . . . ?
O14 S1 C10 F11 61.81(18) . . . . ?
O14 S1 C10 F13 -58.08(18) . . . . ?
N24 C29 C28 C27 -0.5(3) . . . . ?
N24 C25 C26 C27 0.3(3) . . . . ?
N38 C39 C40 C41 1.2(3) . . . . ?
N30 C31 C32 C33 0.2(3) . . . . ?
N30 C35 C34 C33 0.4(3) . . . . ?
N16 C17 C18 C19 -0.6(3) . . . . ?
N2 S1 C10 F12 69.86(18) . . . . ?
N2 S1 C10 F11 -51.10(18) . . . . ?
N2 S1 C10 F13 -170.99(15) . . . . ?
N2 S3 C4 F5 -173.21(16) . . . . ?
N2 S3 C4 F7 -53.09(18) . . . . ?
N2 S3 C4 F6 67.64(19) . . . . ?
C39 N38 C43 C42 -2.0(3) . . . . ?
C29 N24 C25 C26 0.6(3) . . . . ?
C29 C28 C27 C26 1.4(3) . . . . ?
C29 C28 C27 C23 -178.57(19) . . . . ?
C42 C41 C40 C39 -2.2(3) . . . . ?
C42 C41 C37 C36 -42.4(3) . . . . ?
C17 N16 C21 C20 -0.8(3) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C17 C18 C19 C22 179.28(19) . . . . ?
C28 C27 C26 C25 -1.2(3) . . . . ?
C28 C27 C23 C22 -114.2(2) . . . . ?
C41 C42 C43 N38 1.0(3) . . . . ?
C41 C37 C36 C33 -178.6(2) . . . . ?
C25 N24 C29 C28 -0.5(3) . . . . ?
C43 N38 C39 C40 0.9(3) . . . . ?
C43 C42 C41 C40 1.2(3) . . . . ?
C43 C42 C41 C37 -177.2(2) . . . . ?
C31 N30 C35 C34 -2.1(3) . . . . ?
C31 C32 C33 C34 -1.9(3) . . . . ?
C31 C32 C33 C36 178.5(2) . . . . ?
C26 C27 C23 C22 65.9(3) . . . . ?
C40 C41 C37 C36 139.3(2) . . . . ?
C21 N16 C17 C18 1.4(3) . . . . ?
C21 C20 C19 C22 -178.78(19) . . . . ?
C21 C20 C19 C18 1.3(3) . . . . ?
C19 C20 C21 N16 -0.5(3) . . . . ?
C19 C22 C23 C27 -173.86(18) . . . . ?
C35 N30 C31 C32 1.8(3) . . . . ?
C35 C34 C33 C32 1.6(3) . . . . ?
C35 C34 C33 C36 -178.7(2) . . . . ?
C23 C27 C26 C25 178.70(19) . . . . ?
C23 C22 C19 C20 -119.7(2) . . . . ?
C23 C22 C19 C18 60.2(3) . . . . ?
C34 C33 C36 C37 -83.8(3) . . . . ?
C32 C33 C36 C37 95.9(3) . . . . ?
C37 C41 C40 C39 176.2(2) . . . . ?
C10 S1 N2 S3 -92.97(16) . . . . ?
C4 S3 N2 S1 -96.16(16) . . . . ?
Li44 N16 C17 C18 -169.16(17) . . . . ?
Li44 N16 C21 C20 168.76(16) . . . . ?
Li45 N30 C31 C32 -171.27(17) . . . . ?
Li45 N30 C35 C34 171.04(17) . . . . ?
Li46 N24 C29 C28 170.41(19) . . . . ?
Li46 N24 C25 C26 -170.82(19) . . . . ?
Li46 N38 C39 C40 -170.09(19) . . . . ?
Li46 N38 C43 C42 169.90(19) . . . . ?

_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 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.759
####################################################################### 
# 
# 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_230831_8_kageyama_fsg_1_4_3_0degc_auto
_database_code_depnum_ccdc_archive 'CCDC 2463045'
loop_
_audit_author_name
_audit_author_address
'Taichi Nishiguchi'
;Kyoto University
Japan
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2024-02-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F2 N O4 S2, C9 H10 Li N4'
_chemical_formula_sum            'C9 H10 F2 Li N5 O4 S2'
_chemical_formula_weight         361.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Li C11 H10 N3 O4 S2 F6'
_chemical_oxdiff_usercomment     0degC
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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'

_cell_length_a                   5.1756(4)
_cell_length_b                   15.2002(13)
_cell_length_c                   20.2029(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1589.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3805
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.5910
_cell_measurement_theta_min      2.8170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11720
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.203
_diffrn_reflns_theta_min         2.680
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -36.00   0.50    1.19    --    4.00  45.00 150.00   52
  2  ω    -58.00 -32.00   0.50    1.19    --  -16.60  45.00 150.00   52
  3  ω      1.00  34.00   0.50    1.19    --  -16.60  45.00 150.00   66
  4  ω     36.00  62.00   0.50    1.19    --  -16.60  45.00 150.00   52
  5  ω     38.00  63.00   0.50    1.19    --  -16.60  45.00   0.00   50
  6  ω   -106.00  71.00   0.50    1.19    --  -16.60  45.00 120.00  354
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0064414000
_diffrn_orient_matrix_UB_12      -0.0456870000
_diffrn_orient_matrix_UB_13      -0.0068948000
_diffrn_orient_matrix_UB_21      0.0384575000
_diffrn_orient_matrix_UB_22      0.0094762000
_diffrn_orient_matrix_UB_23      -0.0329289000
_diffrn_orient_matrix_UB_31      0.1315221000
_diffrn_orient_matrix_UB_32      -0.0006575000
_diffrn_orient_matrix_UB_33      0.0099185000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1625
_reflns_number_total             2473
_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 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0630
_refine_ls_restrained_S_all      1.059
_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)+(0.0931P)²+0.3026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1841
_refine_ls_wR_factor_ref         0.2039
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Shared sites
{S1, S1A}
3. Restrained distances
 N2-C4 = N2-C4A
 1.136 with sigma of 0.02
 C4-C5 = C4A-C5A
 1.47 with sigma of 0.02
 F1-S1 = F1A-S1A
 1.527 with sigma of 0.02
 O2-S1 = O1-S1 = O2A-S1A = O1A-S1A
 1.428 with sigma of 0.02
 N2-C5 \\sim N2-C5A
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
Uanis(N3) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(S1A) \\sim Ueq, Uanis(O2) \\sim
Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(O2A) \\sim Ueq: with
sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(S1) = Uanis(S1A)
5. Rigid body (RIGU) restrains
 N3, S1, O2, F1, S1A, F1A, O2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C4A)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=1-FVAR(1)
 Sof(C4)=Sof(C5)=Sof(H5A)=Sof(H5B)=FVAR(1)
 Sof(O1A)=Sof(S1A)=Sof(F1A)=Sof(O2A)=1-FVAR(2)
 Sof(S1)=Sof(O1)=Sof(O2)=Sof(F1)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C5A(H5AA,H5AB)
;
_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
O1A O 0.539(5) 0.5509(14) 0.6375(9) 0.159(8) Uani 0.37(2) 1 d D . P A 2
N3 N 0.5472(6) 0.53038(18) 0.750000 0.0788(8) Uani 1 2 d S TU P . .
S1 S 0.48197(15) 0.48534(5) 0.68301(3) 0.0826(3) Uani 0.63(2) 1 d D U P A 1
O1 O 0.5758(19) 0.5337(7) 0.6281(5) 0.102(2) Uani 0.63(2) 1 d D . P A 1
O2 O 0.548(4) 0.3938(5) 0.6826(6) 0.133(3) Uani 0.63(2) 1 d D U P A 1
F1 F 0.1959(12) 0.4894(12) 0.6783(4) 0.166(4) Uani 0.63(2) 1 d D U P A 1
S1A S 0.48197(15) 0.48534(5) 0.68301(3) 0.0826(3) Uani 0.37(2) 1 d D U P A 2
F1A F 0.669(3) 0.4134(10) 0.6733(6) 0.115(4) Uani 0.37(2) 1 d D U P A 2
O2A O 0.240(4) 0.4404(12) 0.6794(8) 0.127(5) Uani 0.37(2) 1 d D U P A 2
N1 N 0.8278(4) 0.23436(14) 0.58172(9) 0.0775(6) Uani 1 1 d . . . . .
N2 N 0.3773(5) 0.35571(15) 0.51264(10) 0.0827(6) Uani 1 1 d D . . . .
C1 C 0.9470(4) 0.22927(13) 0.62833(9) 0.0630(5) Uani 1 1 d . . . . .
C2 C 1.1001(5) 0.22303(17) 0.68837(9) 0.0680(6) Uani 1 1 d . . . . .
H2A H 1.226769 0.270052 0.688876 0.082 Uiso 1 1 calc R U . . .
H2B H 1.192476 0.167513 0.688581 0.082 Uiso 1 1 calc R U . . .
C3 C 0.9340(6) 0.2292(2) 0.750000 0.0636(7) Uani 1 2 d S T P . .
H3A H 0.840926 0.284557 0.750000 0.076 Uiso 1 2 calc R U P . .
H3B H 0.808241 0.181832 0.750000 0.076 Uiso 1 2 calc R U P . .
Li1 Li 0.6068(11) 0.250000 0.500000 0.0683(12) Uani 1 2 d S T P B .
C4 C 0.2533(14) 0.4172(5) 0.5216(4) 0.0655(15) Uani 0.557(13) 1 d D . P B 1
C5 C 0.0624(12) 0.4876(4) 0.5323(2) 0.075(2) Uani 0.557(13) 1 d D . P B 1
H5A H 0.147005 0.538629 0.551259 0.090 Uiso 0.557(13) 1 calc R U P B 1
H5B H -0.068610 0.467616 0.563149 0.090 Uiso 0.557(13) 1 calc R U P B 1
C4A C 0.1890(17) 0.3950(5) 0.5093(5) 0.0638(17) Uani 0.443(13) 1 d D . P B 2
C5A C -0.0396(13) 0.4538(4) 0.5074(5) 0.080(3) Uani 0.443(13) 1 d D . P B 2
H5AA H -0.127720 0.451914 0.549750 0.17(4) Uiso 0.443(13) 1 calc R . P B 2
H5AB H -0.158951 0.433486 0.473693 0.11(2) Uiso 0.443(13) 1 calc R . P B 2


_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
O1A S1A 1.388(14) . ?
N3 S1 1.5537(15) 6_557 ?
N3 S1 1.5538(15) . ?
N3 S1A 1.5538(15) . ?
S1 O1 1.417(7) . ?
S1 O2 1.433(7) . ?
S1 F1 1.485(6) . ?
S1A F1A 1.475(9) . ?
S1A O2A 1.426(12) . ?
N1 C1 1.129(3) . ?
N1 Li1 2.022(4) . ?
N2 Li1 2.015(4) . ?
N2 C4 1.148(7) . ?
N2 C4A 1.145(8) . ?
C1 C2 1.452(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.516(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.472(8) . ?
C5 C5 1.503(9) 5_566 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4A C5A 1.484(9) . ?
C5A C5A 1.493(12) 5_566 ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 N3 S1 121.14(19) 6_557 . ?
O1 S1 N3 112.3(5) . . ?
O1 S1 O2 114.6(7) . . ?
O1 S1 F1 105.6(6) . . ?
O2 S1 N3 112.4(3) . . ?
O2 S1 F1 106.2(5) . . ?
F1 S1 N3 104.7(5) . . ?
O1A S1A N3 102.4(9) . . ?
O1A S1A F1A 107.8(11) . . ?
O1A S1A O2A 119.7(12) . . ?
F1A S1A N3 107.4(6) . . ?
O2A S1A N3 116.5(6) . . ?
O2A S1A F1A 102.4(6) . . ?
C1 N1 Li1 176.8(2) . . ?
C4 N2 Li1 177.3(4) . . ?
C4A N2 Li1 155.6(5) . . ?
N1 C1 C2 179.8(3) . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C1 C2 C3 111.9(2) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C2 C3 C2 110.4(3) 6_557 . ?
C2 C3 H3A 109.6 6_557 . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 6_557 . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N1 Li1 N1 111.1(3) . 4_556 ?
N2 Li1 N1 108.89(8) 4_556 4_556 ?
N2 Li1 N1 110.07(8) 4_556 . ?
N2 Li1 N1 108.89(8) . . ?
N2 Li1 N1 110.07(8) . 4_556 ?
N2 Li1 N2 107.7(3) . 4_556 ?
N2 C4 C5 171.8(6) . . ?
C4 C5 C5 110.1(5) . 5_566 ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C5 C5 H5A 109.6 5_566 . ?
C5 C5 H5B 109.6 5_566 . ?
H5A C5 H5B 108.2 . . ?
N2 C4A C5A 174.1(7) . . ?
C4A C5A C5A 110.7(7) . 5_566 ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
C5A C5A H5AA 109.5 5_566 . ?
C5A C5A H5AB 109.5 5_566 . ?
H5AA C5A H5AB 108.1 . . ?

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
S1 N3 S1 O1 -175.2(5) 6_557 . . . ?
S1 N3 S1 O2 -44.2(10) 6_557 . . . ?
S1 N3 S1 F1 70.7(7) 6_557 . . . ?
C1 C2 C3 C2 -179.62(14) . . . 6_557 ?


_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 4.394
_oxdiff_exptl_absorpt_empirical_full_min 0.586
