#------------------------------------------------------------------------------
#$Date: 2017-10-05 10:45:27 +0300 (Thu, 05 Oct 2017) $
#$Revision: 201758 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/69/1546952.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_1546952
loop_
_publ_author_name
'Wang, Ming'
'Chen, Shihao'
'Jiang, Xuefeng'
_publ_section_title
;
 Construction of Functionalized Annulated Sulfone via SO2/I Exchange of
 Cyclic Diaryliodonium Salts.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4916
_journal_page_last               4919
_journal_paper_doi               10.1021/acs.orglett.7b02388
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C13 H7 F3 O2 S'
_chemical_formula_sum            'C13 H7 F3 O2 S'
_chemical_formula_weight         284.25
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.918(4)
_cell_length_b                   6.9184(12)
_cell_length_c                   8.0372(14)
_cell_measurement_reflns_used    1831
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.26
_cell_measurement_theta_min      2.699
_cell_volume                     1218.7(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13489
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         1.858
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0873 before and 0.0688 after correction. The Ratio of minimum to maximum transmission is 0.7247. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.106
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1167
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0792
_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)+(0.1269P)²+1.5092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2175
_refine_ls_wR_factor_ref         0.2389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                844
_reflns_number_total             1167
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b02388_si_002.cif
_cod_data_source_block           z
_cod_depositor_comments
'Adding full bibliography for 1546950--1546952.cif.'
_cod_original_cell_volume        1218.8(4)
_cod_database_code               1546952
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1-F1 = C1-F2
 1.32 with sigma of 0.01
 F4-C1 = F1-C1 = F3-C1 = F2-C1
 1.38 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1 \\sim F2 \\sim F3 \\sim F1 \\sim F4: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4. Others
 Fixed Sof: F1(0.5) F2(0.25) F3(0.5) F4(0.25)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.43412(8) 0.250000 0.29457(17) 0.0601(7) Uani 1 2 d S T P . .
O1 O 0.42050(18) 0.0723(5) 0.3783(4) 0.0774(12) Uani 1 1 d . . . . .
F1 F 0.2470(5) 0.1625(19) -0.3017(13) 0.152(5) Uani 0.5 1 d D U . A -1
F2 F 0.2214(7) 0.293(3) -0.0287(16) 0.109(6) Uani 0.25 1 d D U . A -1
C1 C 0.2574(5) 0.250000 -0.1584(11) 0.107(3) Uani 1 2 d DS TU P . .
C2 C 0.3237(3) 0.250000 -0.1133(9) 0.0665(18) Uani 1 2 d S T P A .
C3 C 0.3401(3) 0.250000 0.0573(8) 0.0606(17) Uani 1 2 d S T P . .
H3 H 0.310832 0.250000 0.141060 0.073 Uiso 1 2 calc RS T P A .
C4 C 0.4013(3) 0.250000 0.0925(7) 0.0508(15) Uani 1 2 d S T P A .
C5 C 0.5090(3) 0.250000 0.2181(8) 0.0551(16) Uani 1 2 d S T P . .
C6 C 0.5627(4) 0.250000 0.3104(9) 0.0695(19) Uani 1 2 d S T P . .
H6 H 0.561842 0.250000 0.426081 0.083 Uiso 1 2 calc RS T P . .
C7 C 0.6170(4) 0.250000 0.2247(12) 0.081(2) Uani 1 2 d S T P . .
H7 H 0.653619 0.250000 0.283358 0.098 Uiso 1 2 calc RS T P . .
C9 C 0.5645(3) 0.250000 -0.0398(9) 0.0637(18) Uani 1 2 d S T P . .
H9 H 0.565611 0.250000 -0.155456 0.076 Uiso 1 2 calc RS T P . .
C10 C 0.5091(3) 0.250000 0.0432(7) 0.0511(15) Uani 1 2 d S T P A .
C11 C 0.4453(3) 0.250000 -0.0245(6) 0.0395(13) Uani 1 2 d S T P . .
C12 C 0.4290(3) 0.250000 -0.1969(8) 0.0591(17) Uani 1 2 d S T P A .
H12 H 0.458465 0.250000 -0.280206 0.071 Uiso 1 2 calc RS T P . .
C13 C 0.3683(4) 0.250000 -0.2328(8) 0.0675(19) Uani 1 2 d S T P . .
H13 H 0.356538 0.250000 -0.343953 0.081 Uiso 1 2 calc RS T P A .
C8 C 0.6181(4) 0.250000 0.0508(11) 0.073(2) Uani 1 2 d S T P . .
H8 H 0.655326 0.250000 -0.004616 0.087 Uiso 1 2 calc RS T P . .
F3 F 0.2285(5) 0.098(2) -0.098(2) 0.162(4) Uani 0.5 1 d D U . A -2
F4 F 0.2418(9) 0.433(3) -0.211(3) 0.109(5) Uani 0.25 1 d D U . A -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'
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
O1 S1 O1 118.2(3) 7_565
O1 S1 C4 110.18(18) .
O1 S1 C4 110.18(18) 7_565
O1 S1 C5 111.08(19) 7_565
O1 S1 C5 111.08(19) .
C5 S1 C4 93.4(3) .
F1 C1 F2 132.7(13) .
F1 C1 C2 112.3(8) .
F2 C1 C2 112.5(10) .
F3 C1 C2 112.0(7) .
F3 C1 F4 136.6(14) .
F4 C1 C2 108.4(10) .
C3 C2 C1 118.7(7) .
C13 C2 C1 121.5(7) .
C13 C2 C3 119.8(6) .
C2 C3 H3 121.7 .
C4 C3 C2 116.6(6) .
C4 C3 H3 121.7 .
C3 C4 S1 125.8(5) .
C11 C4 S1 110.4(5) .
C11 C4 C3 123.8(6) .
C6 C5 S1 127.3(5) .
C6 C5 C10 122.1(6) .
C10 C5 S1 110.7(5) .
C5 C6 H6 121.1 .
C7 C6 C5 117.8(7) .
C7 C6 H6 121.1 .
C6 C7 H7 119.5 .
C6 C7 C8 120.9(7) .
C8 C7 H7 119.5 .
C10 C9 H9 120.3 .
C8 C9 H9 120.3 .
C8 C9 C10 119.4(7) .
C5 C10 C11 111.1(5) .
C9 C10 C5 119.0(6) .
C9 C10 C11 129.9(6) .
C4 C11 C10 114.4(5) .
C4 C11 C12 119.9(6) .
C12 C11 C10 125.7(5) .
C11 C12 H12 121.7 .
C13 C12 C11 116.7(6) .
C13 C12 H12 121.7 .
C2 C13 H13 118.4 .
C12 C13 C2 123.3(6) .
C12 C13 H13 118.4 .
C7 C8 H8 119.6 .
C9 C8 C7 120.9(7) .
C9 C8 H8 119.6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.433(3) 7_565
S1 O1 1.433(3) .
S1 C4 1.776(6) .
S1 C5 1.752(7) .
F1 C1 1.321(7) .
F2 C1 1.340(9) .
C1 C2 1.498(12) .
C1 F3 1.321(11) .
C1 F4 1.377(14) .
C2 C3 1.417(9) .
C2 C13 1.371(10) .
C3 H3 0.9300 .
C3 C4 1.371(9) .
C4 C11 1.347(8) .
C5 C6 1.391(10) .
C5 C10 1.406(8) .
C6 H6 0.9300 .
C6 C7 1.377(11) .
C7 H7 0.9300 .
C7 C8 1.398(12) .
C9 H9 0.9300 .
C9 C10 1.385(9) .
C9 C8 1.382(10) .
C10 C11 1.502(8) .
C11 C12 1.430(8) .
C12 H12 0.9300 .
C12 C13 1.362(10) .
C13 H13 0.9300 .
C8 H8 0.9300 .
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
S1 C4 C11 C10 0.000(0) .
S1 C4 C11 C12 180.000(0) .
S1 C5 C6 C7 180.000(0) .
S1 C5 C10 C9 180.000(0) .
S1 C5 C10 C11 0.000(0) .
O1 S1 C4 C3 66.1(2) .
O1 S1 C4 C3 -66.1(2) 7_565
O1 S1 C4 C11 113.9(2) 7_565
O1 S1 C4 C11 -113.9(2) .
O1 S1 C5 C6 -66.87(18) .
O1 S1 C5 C6 66.87(18) 7_565
O1 S1 C5 C10 113.13(18) .
O1 S1 C5 C10 -113.13(18) 7_565
F1 C1 C2 C3 -150.3(7) .
F1 C1 C2 C13 29.7(7) .
F2 C1 C2 C3 13.8(11) .
F2 C1 C2 C13 -166.2(11) .
C1 C2 C3 C4 180.000(0) .
C1 C2 C13 C12 180.000(0) .
C2 C3 C4 S1 180.000(0) .
C2 C3 C4 C11 0.000(0) .
C3 C2 C13 C12 0.000(0) .
C3 C4 C11 C10 180.0 .
C3 C4 C11 C12 0.000(0) .
C4 S1 C5 C6 180.000(0) .
C4 S1 C5 C10 0.000(0) .
C4 C11 C12 C13 0.000(0) .
C5 S1 C4 C3 180.0 .
C5 S1 C4 C11 0.000(0) .
C5 C6 C7 C8 0.000(1) .
C5 C10 C11 C4 0.000(0) .
C5 C10 C11 C12 180.000(0) .
C6 C5 C10 C9 0.000(0) .
C6 C5 C10 C11 180.000(0) .
C6 C7 C8 C9 0.000(1) .
C9 C10 C11 C4 180.000(0) .
C9 C10 C11 C12 0.000(0) .
C10 C5 C6 C7 0.000(1) .
C10 C9 C8 C7 0.000(1) .
C10 C11 C12 C13 180.000(0) .
C11 C12 C13 C2 0.000(0) .
C13 C2 C3 C4 0.000(0) .
C8 C9 C10 C5 0.000(0) .
C8 C9 C10 C11 180.0 .
F3 C1 C2 C3 -59.2(10) .
F3 C1 C2 C13 120.8(10) .
F4 C1 C2 C3 104.7(12) .
F4 C1 C2 C13 -75.3(12) .
