Photo-induced tandem cyclization of alkynes with sodium sulfinates to access sulfonated exocyclic alkenes
Xu, Jiefang; Fan, Haoqun; Cao, Feng; Yang , Xiao-hu; Huang, Chunyan; New Journal of Chemistry  (2026) –; doi:10.1039/D6NJ00474A

data_7064372
_publ_section_title
;
 Photo-induced tandem cyclization of alkynes with sodium sulfinates to
 access sulfonated exocyclic alkenes
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7515
_journal_page_last               7519
_journal_paper_doi               10.1039/D6NJ00474A
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C24 H15 Br O2 S2, C3 H7'
_chemical_formula_sum            'C27 H22 Br O2 S2'
_chemical_formula_weight         522.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-04-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-05-07 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9257(3)
_cell_length_b                   16.5073(9)
_cell_length_c                   24.3620(12)
_cell_measurement_reflns_used    6795
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      24.52
_cell_measurement_theta_min      2.61
_cell_volume                     2381.7(2)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_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  0.1201
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            68963
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_min         2.606
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.924
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1867 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.6786.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       block
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5510
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0390P)^2^+0.9927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3467
_reflns_number_total             5510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6nj00474a2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7064372.cif.'
_cod_database_code               7064372
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.831
_shelx_estimated_absorpt_t_min   0.711
_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. Uiso/Uaniso restraints and constraints
C25 \\sim C26 \\sim C27 \\sim C25A \\sim C26A \\sim C27A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Same fragment restrains
{C25A, C26A, C27A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{C25, C26, C27}
4. Others
 Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=Sof(C26A)=Sof(H26C)=Sof(H26D)=
 Sof(C27A)=Sof(H27C)=Sof(H27D)=1-FVAR(1)
 Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=
 Sof(H27A)=Sof(H27B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C26A(H26C,H26D), C27A(H27C,H27D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
5.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C25A(H25D,H25E,H25F)
;
_shelx_res_checksum              8114
_olex2_submission_special_instructions 'No special instructions were received'