Photoredox Catalysis in Alkene and Alkyne Alkylsulfonylations: The Construction of Markovnikov Selective α-Sulfones
Lu, Lingyi; Wang, Haoran; Huang, Shanshan; Xiong, Biao; Zeng, Xiaobao; Ling, Yong; Qiu, Xiaodong; Chemical Communications  (2023) –; doi:10.1039/D3CC02740F

data_7131967
_publ_section_title
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 Photoredox Catalysis in Alkene and Alkyne Alkylsulfonylations: The
 Construction of Markovnikov Selective \a-Sulfones
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02740F
_journal_year                    2023
_chemical_formula_moiety         'C29 H29 F3 O4 S'
_chemical_formula_sum            'C29 H29 F3 O4 S'
_chemical_formula_weight         530.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2fcl7n
_audit_creation_date             2022-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-01 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9381(9)
_cell_length_b                   11.1134(7)
_cell_length_c                   26.1609(14)
_cell_measurement_reflns_used    6743
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.66
_cell_volume                     5215.3(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1188
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            42615
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         1.927
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5085
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1647 before and 0.0868 after correction.
The Ratio of minimum to maximum transmission is 0.6820.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6001
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0810
_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/[\s^2^(Fo^2^)+(0.0276P)^2^+10.2468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1656
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3946
_reflns_number_total             6001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02740f2.cif
_cod_data_source_block           1_a
_cod_database_code               7131967
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C29-F6
 1.35 with sigma of 0.01
 F2-C29 \\sim F3-C29 \\sim F1-C29
 with sigma of 0.02
 F5-C29 \\sim F4-C29 \\sim F6-C29
 with sigma of 0.02
 F1-F2 \\sim F1-F3 \\sim F2-F3
 with sigma of 0.02
 F4-F5 \\sim F4-F6 \\sim F5-F6
 with sigma of 0.02
 C29-F6 \\sim C29-F4 \\sim C29-F5
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F5) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F6) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(F4)=Sof(F5)=Sof(F6)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C7(H7A,H7B), C9(H9A,H9B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,
 H10B), C4(H4A,H4B)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C28(H28), C22(H22), C15(H15), C25(H25), C27(H27), C24(H24),
 C20(H20), C17(H17), C18(H18), C19(H19)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              52818
_shelx_hkl_checksum              71123
_olex2_submission_special_instructions 'No special instructions were received'