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_7160557
_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         'C16 H24 O9 S2'
_chemical_formula_sum            'C16 H24 O9 S2'
_chemical_formula_weight         424.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-10-08 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5662(3)
_cell_length_b                   11.8991(4)
_cell_length_c                   19.6088(7)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.945
_cell_measurement_theta_min      4.346
_cell_volume                     1998.73(12)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2017) '
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 Kappa Duo'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       APEX2
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29973
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_min         4.346
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.02979
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           49.65
_exptl_absorpt_coefficient_mu    2.828
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Krause, 2015) was used for absorption correction.
wR2(int) was 0.0695 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.8953.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1565 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0638P)^2^+0.4904P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3730
_reflns_number_total             3770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00507h3.cif
_cod_data_source_block           tcd2212
_cod_depositor_comments
'Adding full bibliography for 7160555--7160558.cif.'
_cod_database_code               7160557
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.735
_shelx_estimated_absorpt_t_min   0.610
_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
 S23_$1-H23_$1
 0.98 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C27(H27A,H27B,
 H27C)
;
_shelx_res_checksum              5991
_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen microloop'
_olex2_submission_original_sample_id APC-42
_olex2_submission_special_instructions 'No special instructions were received'