Construction of Functionalized Annulated Sulfone via SO2/I Exchange of Cyclic Diaryliodonium Salts.
Wang, Ming; Chen, Shihao; Jiang, Xuefeng; Organic letters 19 (2017) 4916–4919; doi:10.1021/acs.orglett.7b02388

data_1546952
_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       '\f and \w 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 \l/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/[\s^2^(Fo^2^)+(0.1269P)^2^+1.5092P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              29175
_shelx_hkl_checksum              11983
_olex2_submission_special_instructions 'No special instructions were received'