#------------------------------------------------------------------------------
#$Date: 2023-06-29 11:12:17 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284551 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/17/7131763.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_7131763
loop_
_publ_author_name
'Ito, Yuki'
'Adachi, Akiya'
'Aikawa, Kohsuke'
'Nozaki, Kyoko'
'Okazoe, Takashi'
_publ_section_title
;
 N-Fluorobenzenesulfonimide (NFSI) analogs with deprotectable
 substituents: Synthesis of b-fluoroamines via catalytic aminofluorination
 of styrenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02292G
_journal_year                    2023
_chemical_formula_moiety         'C12 H9 F N2 O6 S2'
_chemical_formula_sum            'C12 H9 F N2 O6 S2'
_chemical_formula_weight         360.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2f02j2
_audit_creation_date             2021-07-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.216(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9044(5)
_cell_length_b                   7.9513(3)
_cell_length_c                   15.0809(5)
_cell_measurement_reflns_used    4249
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.4350
_cell_measurement_theta_min      2.1980
_cell_volume                     1423.63(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  53.00   0.50   11.00    --   20.00  54.00  90.00   52
  2  ω    -29.00  17.00   0.50   11.00    --   20.00  54.00 -90.00   92
  3  ω     50.00  76.00   0.50   11.00    --   20.00  54.00 -90.00   52
  4  ω    -41.00  10.00   0.50   11.00    --   20.00  54.00-120.00  102
  5  ω    -74.00 106.00   0.50   11.00    --   20.00  54.00 120.00  360
  6  ω    -60.00 -35.00   0.50   11.00    --   20.00  54.00  90.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6944
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.262
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0316
_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)+(0.0489P)²+0.4463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0898
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2362
_reflns_number_total             2826
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc02292g2.cif
_cod_data_source_block           nsbsnf_auto
_cod_database_code               7131763
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.850
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N)
;
_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
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
S001 S 0.20793(4) 0.37946(5) 0.56346(3) 0.02098(13) Uani 1 1 d . . . . .
S002 S 0.41644(4) 0.38657(5) 0.69437(3) 0.02081(13) Uani 1 1 d . . . . .
F003 F 0.39908(9) 0.48689(14) 0.53383(7) 0.0300(3) Uani 1 1 d . . . . .
O004 O 0.50962(12) 0.49805(16) 0.70101(9) 0.0322(3) Uani 1 1 d . . . . .
O005 O 0.34098(12) 0.37409(17) 0.76260(8) 0.0305(3) Uani 1 1 d . . . . .
O006 O 0.14247(12) 0.36477(19) 0.63727(9) 0.0365(4) Uani 1 1 d . . . . .
O007 O 0.23350(13) 0.23760(16) 0.51150(9) 0.0360(4) Uani 1 1 d . . . . .
O008 O 0.08364(14) 0.2788(2) 0.35835(10) 0.0456(4) Uani 1 1 d . . . . .
N009 N 0.33086(12) 0.47434(18) 0.60704(9) 0.0196(3) Uani 1 1 d . . . . .
N00A N 0.16026(16) 0.3790(2) 0.35412(11) 0.0340(4) Uani 1 1 d . . . . .
C00B C 0.16132(14) 0.5474(2) 0.49435(11) 0.0192(4) Uani 1 1 d . . . . .
C00C C 0.45844(15) 0.1890(2) 0.65964(11) 0.0188(4) Uani 1 1 d . . . . .
O00D O 0.24203(17) 0.3609(3) 0.31128(13) 0.0654(6) Uani 1 1 d . . . . .
C00E C 0.56183(16) 0.1721(2) 0.62404(12) 0.0249(4) Uani 1 1 d . . . . .
H00E H 0.608769 0.267027 0.616990 0.030 Uiso 1 1 calc R U . . .
C00F C 0.38841(16) 0.0525(2) 0.67118(12) 0.0244(4) Uani 1 1 d . . . . .
H00F H 0.317816 0.066914 0.695755 0.029 Uiso 1 1 calc R U . . .
C00G C 0.15114(15) 0.5390(2) 0.40193(12) 0.0233(4) Uani 1 1 d . . . . .
C00H C 0.14394(16) 0.7004(2) 0.53566(13) 0.0273(4) Uani 1 1 d . . . . .
H00H H 0.149298 0.707582 0.598709 0.033 Uiso 1 1 calc R U . . .
C00I C 0.52633(18) -0.1240(2) 0.61022(13) 0.0300(5) Uani 1 1 d . . . . .
H00I H 0.549933 -0.232623 0.593076 0.036 Uiso 1 1 calc R U . . .
C00J C 0.42359(18) -0.1046(2) 0.64615(13) 0.0293(5) Uani 1 1 d . . . . .
H00J H 0.377059 -0.199894 0.653637 0.035 Uiso 1 1 calc R U . . .
C00K C 0.59497(17) 0.0133(3) 0.59903(13) 0.0304(4) Uani 1 1 d . . . . .
H00K H 0.665269 -0.001335 0.574036 0.036 Uiso 1 1 calc R U . . .
C00L C 0.11892(18) 0.8419(3) 0.48514(16) 0.0375(5) Uani 1 1 d . . . . .
H00L H 0.106947 0.946462 0.513465 0.045 Uiso 1 1 calc R U . . .
C00M C 0.12704(17) 0.6808(3) 0.35160(13) 0.0355(5) Uani 1 1 d . . . . .
H00M H 0.121356 0.674349 0.288530 0.043 Uiso 1 1 calc R U . . .
C00N C 0.11123(18) 0.8320(3) 0.39353(16) 0.0423(6) Uani 1 1 d . . . . .
H00N H 0.094902 0.930257 0.359099 0.051 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-13 -3 13 0.0583
-12 -8 2 0.1332
-11 4 -13 0.1210
-11 0 17 0.0774
-6 10 -3 0.1805
-3 11 1 0.1950
-1 -10 -8 0.1821
6 9 10 0.2013
8 6 14 0.1783
11 0 -18 0.1112
11 -1 15 0.1317
12 2 -15 0.1009
13 6 -8 0.1513
8 -9 6 0.0953
11 -6 11 0.1106
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
O006 S001 O007 121.57(9) . . ?
O006 S001 N009 103.71(8) . . ?
O006 S001 C00B 111.24(9) . . ?
O007 S001 N009 110.24(8) . . ?
O007 S001 C00B 110.34(8) . . ?
N009 S001 C00B 96.61(7) . . ?
O004 S002 O005 121.77(9) . . ?
O004 S002 N009 102.30(7) . . ?
O004 S002 C00C 110.18(8) . . ?
O005 S002 N009 102.07(8) . . ?
O005 S002 C00C 111.49(8) . . ?
C00C S002 N009 107.31(8) . . ?
S001 N009 S002 122.73(8) . . ?
F003 N009 S001 104.53(9) . . ?
F003 N009 S002 106.16(9) . . ?
O008 N00A C00G 117.29(17) . . ?
O00D N00A O008 125.66(19) . . ?
O00D N00A C00G 117.00(19) . . ?
C00G C00B S001 123.88(14) . . ?
C00H C00B S001 116.76(13) . . ?
C00H C00B C00G 119.09(17) . . ?
C00E C00C S002 119.18(14) . . ?
C00E C00C C00F 122.12(17) . . ?
C00F C00C S002 118.67(14) . . ?
C00C C00E H00E 120.9 . . ?
C00K C00E C00C 118.29(18) . . ?
C00K C00E H00E 120.9 . . ?
C00C C00F H00F 120.8 . . ?
C00J C00F C00C 118.50(17) . . ?
C00J C00F H00F 120.8 . . ?
C00B C00G N00A 121.90(16) . . ?
C00M C00G N00A 117.25(17) . . ?
C00M C00G C00B 120.79(18) . . ?
C00B C00H H00H 120.0 . . ?
C00L C00H C00B 120.00(18) . . ?
C00L C00H H00H 120.0 . . ?
C00J C00I H00I 119.7 . . ?
C00K C00I H00I 119.7 . . ?
C00K C00I C00J 120.54(17) . . ?
C00F C00J C00I 120.23(18) . . ?
C00F C00J H00J 119.9 . . ?
C00I C00J H00J 119.9 . . ?
C00E C00K H00K 119.8 . . ?
C00I C00K C00E 120.32(19) . . ?
C00I C00K H00K 119.8 . . ?
C00H C00L H00L 119.9 . . ?
C00H C00L C00N 120.1(2) . . ?
C00N C00L H00L 119.9 . . ?
C00G C00M H00M 120.3 . . ?
C00G C00M C00N 119.43(18) . . ?
C00N C00M H00M 120.3 . . ?
C00L C00N H00N 119.7 . . ?
C00M C00N C00L 120.52(19) . . ?
C00M C00N H00N 119.7 . . ?
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
S001 O006 1.4098(14) . ?
S001 O007 1.4192(14) . ?
S001 N009 1.7324(15) . ?
S001 C00B 1.7585(17) . ?
S002 O004 1.4177(14) . ?
S002 O005 1.4182(14) . ?
S002 N009 1.7500(14) . ?
S002 C00C 1.7407(17) . ?
F003 N009 1.4213(17) . ?
O008 N00A 1.216(2) . ?
N00A O00D 1.216(2) . ?
N00A C00G 1.470(2) . ?
C00B C00G 1.392(2) . ?
C00B C00H 1.389(2) . ?
C00C C00E 1.385(3) . ?
C00C C00F 1.388(2) . ?
C00E H00E 0.9500 . ?
C00E C00K 1.383(3) . ?
C00F H00F 0.9500 . ?
C00F C00J 1.379(3) . ?
C00G C00M 1.377(3) . ?
C00H H00H 0.9500 . ?
C00H C00L 1.379(3) . ?
C00I H00I 0.9500 . ?
C00I C00J 1.382(3) . ?
C00I C00K 1.382(3) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00L C00N 1.380(3) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.378(3) . ?
C00N H00N 0.9500 . ?
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
S001 C00B C00G N00A 10.7(3) . . . . ?
S001 C00B C00G C00M -172.22(15) . . . . ?
S001 C00B C00H C00L 173.19(15) . . . . ?
S002 C00C C00E C00K 178.31(14) . . . . ?
S002 C00C C00F C00J -177.99(14) . . . . ?
O004 S002 N009 S001 174.87(10) . . . . ?
O004 S002 N009 F003 55.09(11) . . . . ?
O004 S002 C00C C00E -14.65(17) . . . . ?
O004 S002 C00C C00F 163.37(13) . . . . ?
O005 S002 N009 S001 -58.42(11) . . . . ?
O005 S002 N009 F003 -178.21(10) . . . . ?
O005 S002 C00C C00E -153.03(14) . . . . ?
O005 S002 C00C C00F 24.98(16) . . . . ?
O006 S001 N009 S002 58.21(12) . . . . ?
O006 S001 N009 F003 178.77(10) . . . . ?
O006 S001 C00B C00G -137.71(16) . . . . ?
O006 S001 C00B C00H 48.29(17) . . . . ?
O007 S001 N009 S002 -73.42(12) . . . . ?
O007 S001 N009 F003 47.13(11) . . . . ?
O007 S001 C00B C00G 0.29(18) . . . . ?
O007 S001 C00B C00H -173.71(15) . . . . ?
O008 N00A C00G C00B 70.4(2) . . . . ?
O008 N00A C00G C00M -106.8(2) . . . . ?
N009 S001 C00B C00G 114.77(16) . . . . ?
N009 S001 C00B C00H -59.23(16) . . . . ?
N009 S002 C00C C00E 95.98(15) . . . . ?
N009 S002 C00C C00F -86.01(15) . . . . ?
N00A C00G C00M C00N 176.28(19) . . . . ?
C00B S001 N009 S002 172.02(10) . . . . ?
C00B S001 N009 F003 -67.43(10) . . . . ?
C00B C00G C00M C00N -1.0(3) . . . . ?
C00B C00H C00L C00N -0.1(3) . . . . ?
C00C S002 N009 S001 58.91(12) . . . . ?
C00C S002 N009 F003 -60.87(11) . . . . ?
C00C C00E C00K C00I -0.5(3) . . . . ?
C00C C00F C00J C00I -0.2(3) . . . . ?
O00D N00A C00G C00B -112.0(2) . . . . ?
O00D N00A C00G C00M 70.8(2) . . . . ?
C00E C00C C00F C00J 0.0(3) . . . . ?
C00F C00C C00E C00K 0.4(3) . . . . ?
C00G C00B C00H C00L -1.1(3) . . . . ?
C00G C00M C00N C00L -0.3(3) . . . . ?
C00H C00B C00G N00A -175.46(17) . . . . ?
C00H C00B C00G C00M 1.6(3) . . . . ?
C00H C00L C00N C00M 0.8(3) . . . . ?
C00J C00I C00K C00E 0.3(3) . . . . ?
C00K C00I C00J C00F 0.1(3) . . . . ?
