Visible-light-driven graphitic carbon nitride-catalyzed ATRA of alkynes: highly regio- and stereoselective synthesis of (E)-β-functionalized vinylsulfones
Xie, Shu-Li; Yan, Jian-Zhong; Xie, Meng-Jun; Li, Xuan; Zhou, Fan; Zheng, Mei-Qiong; Wang, Xue-Lin; Feng, Junhao; Zhang, Yao; Duan, Ya-Nan; Niu, Yong-Dong; Li, Dong; Xia, Hai-Dong; Green Chemistry 26 (2024) 323–329; doi:10.1039/D3GC02897F

data_7247521
_publ_section_title
;
 Visible-light-driven graphitic carbon nitride-catalyzed ATRA of alkynes:
 highly regio- and stereoselective synthesis of (E)-\b-functionalized
 vinylsulfones
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              323
_journal_page_last               329
_journal_paper_doi               10.1039/D3GC02897F
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C22 H18 O3 S Se'
_chemical_formula_sum            'C22 H18 O3 S Se'
_chemical_formula_weight         441.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-19 deposited with the CCDC.	2023-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                83.579(2)
_cell_angle_beta                 82.280(2)
_cell_angle_gamma                64.680(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2763(2)
_cell_length_b                   7.6736(3)
_cell_length_c                   18.9654(5)
_cell_measurement_reflns_used    5919
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.7310
_cell_measurement_theta_min      4.6930
_cell_volume                     946.79(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -16.00  22.00   0.50    0.50    --    0.00  38.00-180.00   76
  2  \w     40.00  87.00   0.50    0.50    --    0.00  38.00-180.00   94
  3  \w    -32.00  17.00   0.50    0.50    --    0.00 -38.00-180.00   98
  4  \w    -87.00 -50.00   0.50    0.50    --    0.00 -38.00-180.00   74
  5  \w      3.00  42.00   0.50    0.50    --   89.30 -82.00-180.00   78
  6  \w     79.00 120.00   0.50    0.50    --   89.30 -82.00-180.00   82
  7  \w      0.00 108.00   0.50    0.50    --   89.30 -61.00 120.00  216
  8  \w     12.00  38.00   0.50    0.50    --   89.30 -82.00  30.00   52
  9  \w     44.00 103.00   0.50    0.50    --   89.30 -30.00-120.00  118
 10  \w     51.00 110.00   0.50    0.50    --   89.30 -82.00  30.00  118
 11  \w     75.00 167.00   0.50    0.50    --   89.30  45.00-120.00  184
 12  \w      1.00  39.00   0.50    0.50    --   89.30 -82.00 120.00   76
 13  \w    119.00 165.00   0.50    0.50    --   89.30  45.00 -30.00   92
 14  \w     28.00  71.00   0.50    0.50    --   89.30 -82.00 -90.00   86
 15  \w     81.00 110.00   0.50    0.50    --   89.30 -82.00 -90.00   58
 16  \w      3.00  94.00   0.50    0.50    --   89.30 -61.00  30.00  182
 17  \w     12.00 104.00   0.50    0.50    --   89.30 -61.00 -90.00  184
 18  \w     60.00 109.00   0.50    0.50    --   89.30 -82.00 120.00   98
 19  \w    110.00 179.00   0.50    0.50    --   89.30  45.00-150.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0041967000
_diffrn_orient_matrix_UB_12      -0.1910681000
_diffrn_orient_matrix_UB_13      -0.0154557000
_diffrn_orient_matrix_UB_21      -0.1342732000
_diffrn_orient_matrix_UB_22      0.0054944000
_diffrn_orient_matrix_UB_23      0.0705624000
_diffrn_orient_matrix_UB_31      -0.1932021000
_diffrn_orient_matrix_UB_32      0.1138981000
_diffrn_orient_matrix_UB_33      -0.0390707000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7774
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.046
_diffrn_reflns_theta_min         4.715
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.836
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     252
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0675P)^2^+0.6660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3300
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02897f2.cif
_cod_data_source_block           20230315bhxc
_cod_depositor_comments          'Adding full bibliography for 7247521.cif.'
_cod_database_code               7247521
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O S Se'
_chemical_oxdiff_usercomment     'Se youjiwu'
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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. Restrained distances
 C16-C7 \\sim C16A-C7
 with sigma of 0.02
 C16-C21 \\sim C16A-C21A
 with sigma of 0.02
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 C20-C19 \\sim C20A-C19A
 with sigma of 0.02
 C19-C18 \\sim C19A-C18A
 with sigma of 0.02
 C19-C22 \\sim C19A-C22A
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C22-O3 \\sim C22A-O3A
 with sigma of 0.02
 C16-C20 \\sim C16A-C20A
 with sigma of 0.04
 C16-C18 \\sim C16A-C18A
 with sigma of 0.04
 C7-C21 \\sim C7-C21A
 with sigma of 0.04
 C7-C17 \\sim C7-C17A
 with sigma of 0.04
 C20-C18 \\sim C20A-C18A
 with sigma of 0.04
 C20-C22 \\sim C20A-C22A
 with sigma of 0.04
 C21-C19 \\sim C21A-C19A
 with sigma of 0.04
 C21-C17 \\sim C21A-C17A
 with sigma of 0.04
 C19-C17 \\sim C19A-C17A
 with sigma of 0.04
 C19-O3 \\sim C19A-O3A
 with sigma of 0.04
 C18-C22 \\sim C18A-C22A
 with sigma of 0.04
3. Restrained planarity
 C7, C16, C17, C18, C19, C20, C21, C22
 with sigma of 0.1
 C7, C16A, C17A, C18A, C19A, C20A, C21A, C22A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O3 \\sim C22: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
C16 \\sim C16A \\sim C17 \\sim C17A \\sim C18 \\sim C18A \\sim C19 \\sim C19A
\\sim C20 \\sim C20A \\sim C21 \\sim C21A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C16) = Uanis(C16A)
Uanis(C17) = Uanis(C17A)
Uanis(C18A) = Uanis(C18)
Uanis(C19A) = Uanis(C19)
Uanis(C20A) = Uanis(C20)
Uanis(C21A) = Uanis(C21)
Uanis(C22A) = Uanis(C22)
Uanis(O3A) = Uanis(O3)
5. Others
 Sof(O3A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
 Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=1-FVAR(1)
 Sof(O3)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(C20)=
 Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C17A(H17A), C18(H18), C18A(H18A), C20(H20), C20A(H20A),
 C21(H21), C21A(H21A), C22(H22), C22A(H22A)
6.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              30911
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.341
_oxdiff_exptl_absorpt_empirical_full_min 0.771