#------------------------------------------------------------------------------
#$Date: 2026-03-05 13:32:50 +0100 (Thu 05 de Mar de 2026) $
#$Revision: 304889 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/66/1576601.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1576601
loop_
_publ_author_name
'Nishiguchi, Taichi'
'Kageyama, Kotoha'
'Kurihara, Takuya'
'Shimanaka, Nanae'
'Tokuda, Shun'
'Tsuda, Shuto'
'Ma, Nattapol'
'Horike, Satoshi'
_publ_section_title
;
 Soft crystalline properties of 2D frameworks constructed from lithium
 ions and dinitriles.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              3669
_journal_page_last               3674
_journal_paper_doi               10.1039/d5sc06222e
_journal_volume                  17
_journal_year                    2026
_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
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-06-10 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1756(4)
_cell_length_b                   15.2002(13)
_cell_length_c                   20.2029(15)
_cell_measurement_reflns_used    3805
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.5910
_cell_measurement_theta_min      2.8170
_cell_volume                     1589.4(2)
_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)'
_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_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_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_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
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.058
_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_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0630
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1625
_reflns_number_total             2473
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc06222e2.cif
_cod_data_source_block           230831_8_kageyama_fsg_1_4_3_0degc_auto
_cod_depositor_comments
'Adding full bibliography for 1576599--1576601.cif.'
_cod_database_code               1576601
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'Li C11 H10 N3 O4 S2 F6'
_chemical_oxdiff_usercomment     0degC
_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.
;
_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)
;
_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
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'
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
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'
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_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_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 ?
