#------------------------------------------------------------------------------
#$Date: 2023-10-06 03:44:19 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286784 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159546.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_7159546
loop_
_publ_author_name
'Ma, Yuyang'
'Pan, Qijun'
'Ou, Caiyun'
'Cai, Yinxia'
'Ma, Xiaoyu'
'Liu, Chao'
_publ_section_title
;
 Aryl sulfonyl fluoride synthesis via organophotocatalytic
 fluorosulfonylation of diaryliodonium salts.
;
_journal_issue                   37
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7597
_journal_page_last               7601
_journal_paper_doi               10.1039/d3ob01200j
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C9 H11 F O2 S'
_chemical_formula_weight         202.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-11-18 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.407(2)
_cell_length_b                   7.2877(13)
_cell_length_c                   9.8840(17)
_cell_measurement_reflns_used    2439
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.833
_cell_measurement_theta_min      8.791
_cell_volume                     965.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4423
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         4.395
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.16(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1006
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0657P)²+0.1681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                859
_reflns_number_total             1006
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01200j2.cif
_cod_data_source_block           d8v21630
_cod_depositor_comments          'Adding full bibliography for 7159546.cif.'
_cod_database_code               7159546
_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_min   0.940
_shelx_estimated_absorpt_t_max   0.963
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
S1 S 0.59647(5) 0.2500 0.73558(6) 0.0718(4) Uani 1 2 d S T P . .
O1 O 0.50379(18) 0.2500 0.7980(2) 0.1145(10) Uani 1 2 d S T P A .
F1 F 0.6669(11) 0.399(2) 0.7641(15) 0.092(3) Uani 0.5 1 d . U P A 1
O2 O 0.6455(15) 0.424(2) 0.7810(17) 0.086(3) Uani 0.5 1 d . U P A 2
C1 C 0.58958(15) 0.2500 0.5585(2) 0.0491(6) Uani 1 2 d S T P A .
C2 C 0.49654(16) 0.2500 0.4938(2) 0.0481(5) Uani 1 2 d S T P . .
C3 C 0.49722(18) 0.2500 0.3537(2) 0.0569(6) Uani 1 2 d S T P A .
H3 H 0.4364 0.2500 0.3085 0.068 Uiso 1 2 calc R U P . .
C4 C 0.58322(19) 0.2500 0.2781(2) 0.0611(7) Uani 1 2 d S T P . .
C5 C 0.6732(2) 0.2500 0.3453(3) 0.0648(7) Uani 1 2 d S T P A .
H5 H 0.7318 0.2500 0.2948 0.078 Uiso 1 2 calc R U P . .
C6 C 0.67972(17) 0.2500 0.4855(3) 0.0580(6) Uani 1 2 d S T P . .
C7 C 0.7827(2) 0.2500 0.5463(5) 0.0934(11) Uani 1 2 d DS T P A .
C8 C 0.39590(19) 0.2500 0.5624(3) 0.0680(7) Uani 1 2 d S T P A .
C9 C 0.5786(4) 0.2500 0.1253(3) 0.0960(12) Uani 1 2 d DS T P A .
H7A H 0.830(2) 0.2500 0.476(3) 0.126(14) Uiso 1 2 d DS . P . .
H8A H 0.3864(14) 0.146(3) 0.626(2) 0.090(7) Uiso 1 1 d . . . . .
H9A H 0.5419(19) 0.148(3) 0.093(3) 0.147(11) Uiso 1 1 d D . . . .
H7B H 0.7920(19) 0.158(3) 0.612(2) 0.134(11) Uiso 1 1 d D . . . .
H8B H 0.340(3) 0.2500 0.497(4) 0.096(10) Uiso 1 2 d S . P . .
H9B H 0.644(2) 0.2500 0.080(5) 0.19(2) Uiso 1 2 d DS . P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 S1 F1 119.4(5) . . ?
O1 S1 F1 119.4(5) . 7_565 ?
F1 S1 F1 95.6(11) . 7_565 ?
O1 S1 O2 105.1(7) . 7_565 ?
O1 S1 O2 105.1(7) . . ?
O2 S1 O2 115.6(14) 7_565 . ?
O1 S1 C1 113.39(12) . . ?
F1 S1 C1 103.1(6) . . ?
F1 S1 C1 103.1(6) 7_565 . ?
O2 S1 C1 108.9(7) 7_565 . ?
O2 S1 C1 108.9(7) . . ?
C2 C1 C6 122.0(2) . . ?
C2 C1 S1 120.14(16) . . ?
C6 C1 S1 117.82(16) . . ?
C3 C2 C1 116.7(2) . . ?
C3 C2 C8 117.1(2) . . ?
C1 C2 C8 126.2(2) . . ?
C4 C3 C2 123.3(2) . . ?
C4 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C9 120.6(3) . . ?
C5 C4 C9 121.2(3) . . ?
C4 C5 C6 122.4(2) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 117.2(2) . . ?
C5 C6 C7 117.2(3) . . ?
C1 C6 C7 125.6(2) . . ?
C6 C7 H7A 109(2) . . ?
C6 C7 H7B 113.3(17) . . ?
H7A C7 H7B 115(2) . . ?
C2 C8 H8A 113.5(11) . . ?
C2 C8 H8B 112.3(19) . . ?
H8A C8 H8B 108.6(17) . . ?
C4 C9 H9A 111(2) . . ?
C4 C9 H9B 115(3) . . ?
H9A C9 H9B 108(3) . . ?
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 O1 1.387(2) . ?
S1 F1 1.466(16) . ?
S1 F1 1.466(16) 7_565 ?
S1 O2 1.495(19) 7_565 ?
S1 O2 1.495(19) . ?
S1 C1 1.753(2) . ?
C1 C2 1.402(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.385(3) . ?
C2 C8 1.510(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 C9 1.512(4) . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(4) . ?
C7 H7A 0.943(19) . ?
C7 H7B 0.939(17) . ?
C8 H8A 0.99(2) . ?
C8 H8B 0.99(4) . ?
C9 H9A 0.946(17) . ?
C9 H9B 0.98(2) . ?
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
O1 S1 C1 C2 0.000(0) . . . . ?
F1 S1 C1 C2 -130.5(5) . . . . ?
F1 S1 C1 C2 130.5(5) 7_565 . . . ?
O2 S1 C1 C2 116.6(7) 7_565 . . . ?
O2 S1 C1 C2 -116.6(7) . . . . ?
O1 S1 C1 C6 180.000(0) . . . . ?
F1 S1 C1 C6 49.5(5) . . . . ?
F1 S1 C1 C6 -49.5(5) 7_565 . . . ?
O2 S1 C1 C6 -63.4(7) 7_565 . . . ?
O2 S1 C1 C6 63.4(7) . . . . ?
C6 C1 C2 C3 0.000(0) . . . . ?
S1 C1 C2 C3 180.000(0) . . . . ?
C6 C1 C2 C8 180.000(0) . . . . ?
S1 C1 C2 C8 0.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C8 C2 C3 C4 180.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C2 C3 C4 C9 180.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C9 C4 C5 C6 180.000(0) . . . . ?
C4 C5 C6 C1 0.000(0) . . . . ?
C4 C5 C6 C7 180.000(0) . . . . ?
C2 C1 C6 C5 0.000(0) . . . . ?
S1 C1 C6 C5 180.000(0) . . . . ?
C2 C1 C6 C7 180.000(0) . . . . ?
S1 C1 C6 C7 0.000(1) . . . . ?
