Photoinitiated thiol-ene mediated functionalisation of 4,5-enoses.
Prieto-Castañeda, Alejandro; Martin, Harlei; Manna, Tapasi; Beswick, Laura; McLean, Joshua T.; Pongener, Imlirenla; González, Inés Rabadán; Twamley, Brendan; Miller, Gavin J.; Scanlan, Eoin M.; Organic & biomolecular chemistry 23 (2025) 5332–5338; doi:10.1039/d5ob00507h

data_7160558
_publ_section_title
;
 Photoinitiated thiol-ene mediated functionalisation of 4,5-enoses.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5332
_journal_page_last               5338
_journal_paper_doi               10.1039/d5ob00507h
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H22 O9 S2'
_chemical_formula_sum            'C15 H22 O9 S2'
_chemical_formula_weight         410.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-09-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-10-08 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.8088(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1283(3)
_cell_length_b                   7.6491(2)
_cell_length_c                   11.5435(3)
_cell_measurement_reflns_used    7967
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.526
_cell_measurement_theta_min      2.607
_cell_volume                     981.42(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX 4 (Bruker, 2021) '
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS Mixed Mode detector'
_diffrn_detector_type            'Bruker PHOTON III C7'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO PhotonIII C7'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_detector       'Bruker PHOTON III C7'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27083
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_min         3.196
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Krause, 2015) was used for absorption correction.
wR2(int) was 0.0735 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.8584.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1465 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4871
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0541P)^2^+0.0190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1080
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3775
_reflns_number_total             4871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00507h3.cif
_cod_data_source_block           tcd2392
_cod_depositor_comments
'Adding full bibliography for 7160555--7160558.cif.'
_cod_database_code               7160558
_shelx_shelxl_version_number     2019/1
_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
 S2-H2
 1.15 with sigma of 0.02
 O23-C24B \\sim O23-C24A
 with sigma of 0.02
 C26B-C24B \\sim C26A-C24A
 with sigma of 0.02
 O25B-C24B \\sim O25A-C24A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O25A) \\sim Ueq, Uanis(C24A) \\sim Ueq, Uanis(C26A) \\sim Ueq,
Uanis(O25B) \\sim Ueq, Uanis(C24B) \\sim Ueq, Uanis(C26B) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C26B) = Uanis(C26A)
4. Rigid body (RIGU) restrains
 O25B, C24B, C26B, O25A, C24A, C26A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O25B)=Sof(C24B)=Sof(C26B)=Sof(H26A)=Sof(H26B)=Sof(H26C)=1-FVAR(1)
 Sof(O25A)=Sof(C24A)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
6.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C26B(H26A,H26B,
 H26C), C26A(H26D,H26E,H26F)
;
_shelx_res_checksum              98397
_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen microloop'
_olex2_submission_original_sample_id 'APC-39.4 F1'
_olex2_submission_special_instructions 'No special instructions were received'