Transition metal-free C(sp<sup>3</sup>)-H selenation of β-ketosulfones.
Abdukerem, Dilshat; Chen, Hui; Mao, Zechuan; Xia, Kun; Zhu, Wenli; Liu, Changhong; Yu, Yuming; Abdukader, Ablimit; Organic & biomolecular chemistry 22 (2024) 2075–2080; doi:10.1039/d4ob00006d

data_7159806
_publ_section_title
;
 Transition metal-free C(sp<sup>3</sup>)-H selenation of
 &#x3b2;-ketosulfones.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2075
_journal_page_last               2080
_journal_paper_doi               10.1039/d4ob00006d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C21 H18 O3 S Se'
_chemical_formula_sum            'C21 H18 O3 S Se'
_chemical_formula_weight         429.37
_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_creation_date             2023-06-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-13 deposited with the CCDC.	2024-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.800(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.005(4)
_cell_length_b                   11.035(4)
_cell_length_c                   18.194(7)
_cell_measurement_reflns_used    3351
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.352
_cell_measurement_theta_min      2.287
_cell_volume                     1966.3(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.965
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11408
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.928
_diffrn_reflns_theta_min         2.159
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.033
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0924 before and 0.0520 after correction.
The Ratio of minimum to maximum transmission is 0.7635.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             872
_refine_diff_density_max         2.547
_refine_diff_density_min         -1.517
_refine_diff_density_rms         0.215
_refine_ls_extinction_coef       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.1795
_refine_ls_R_factor_gt           0.1494
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1075P)^2^+64.9128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3917
_refine_ls_wR_factor_ref         0.4049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3182
_reflns_number_total             4544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00006d2.cif
_cod_data_source_block           230616h1_0m
_cod_depositor_comments          'Adding full bibliography for 7159806.cif.'
_cod_original_cell_volume        1966.2(13)
_cod_database_code               7159806
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C18(H18), C20(H20), C21(H21), C11(H11), C3(H3), C13(H13),
 C15(H15), C2(H2), C17(H17), C9(H9), C19(H19), C5(H5)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              60038
_olex2_submission_special_instructions 'No special instructions were received'