Single electron/energy transfer photocatalysis: α-/β-switchable synthesis of 3-deoxy-d-manno-oct-2-ulosonic acid <i>O</i>-glycosides.
Zhang, Jing-Dong; Jie, Jia-Long; Yan, Shu-Yi; Zhang, Hui; Chen, Jia-Meng; Wu, Jiang-Cheng; Qin, Lu-Yang; Liu, Guang-Jian; Su, Hong-Mei; Xing, Guo-Wen; Chemical science 16 (2025) 13070–13081; doi:10.1039/d5sc02980e

data_1574863
_publ_section_title
;
 Single electron/energy transfer photocatalysis:
 &#x3b1;-/&#x3b2;-switchable synthesis of 3-deoxy-d-manno-oct-2-ulosonic
 acid <i>O</i>-glycosides.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              13070
_journal_page_last               13081
_journal_paper_doi               10.1039/d5sc02980e
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C30 H44 O17'
_chemical_formula_sum            'C30 H44 O17'
_chemical_formula_weight         676.65
_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   geom
_audit_creation_date             2023-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-09-10 deposited with the CCDC.	2025-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.19414(11)
_cell_length_b                   11.29721(14)
_cell_length_c                   28.9840(3)
_cell_measurement_reflns_used    10573
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2070
_cell_measurement_theta_min      4.2570
_cell_volume                     3337.95(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_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   -100.00 -41.00   0.50    0.05    -- -102.00 104.00 124.00  118
  2  \w    -67.00   4.00   0.50    0.05    --  -46.92 104.00 124.00  142
  3  \w    -71.00 -29.00   0.50    0.05    -- -102.00  66.00  37.00   84
  4  \w    -61.00 -30.00   0.50    0.05    -- -102.00  61.00   0.00   62
  5  \w    -63.00 -37.00   0.50    0.05    -- -102.00  61.00 -30.00   52
  6  \w   -165.00 -89.00   0.50    0.05    -- -102.00 -59.00 110.00  152
  7  \w   -116.00 -91.00   0.50    0.05    --  -46.92-125.00 -90.00   50
  8  \w   -116.00 -83.00   0.50    0.05    --  -46.92-125.00-150.00   66
  9  \w   -116.00 -71.00   0.50    0.05    --  -46.92-125.00-180.00   90
 10  \w     32.00  68.00   0.50    0.05    --  104.75 -66.00 -97.00   72
 11  \w     48.00  73.00   0.50    0.05    --  104.75 -61.00  30.00   50
 12  \w     35.00  68.00   0.50    0.05    --  104.75 -61.00  60.00   66
 13  \w    121.00 178.00   0.50    0.05    --  104.75  30.00 -30.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1000973000
_diffrn_orient_matrix_UB_12      -0.0359661000
_diffrn_orient_matrix_UB_13      0.0372759000
_diffrn_orient_matrix_UB_21      0.0571178000
_diffrn_orient_matrix_UB_22      -0.1262791000
_diffrn_orient_matrix_UB_23      0.0004504000
_diffrn_orient_matrix_UB_31      0.0977091000
_diffrn_orient_matrix_UB_32      0.0369078000
_diffrn_orient_matrix_UB_33      0.0378898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12432
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.467
_diffrn_reflns_theta_min         4.200
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.85a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 2013 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0915P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.604
_reflns_Friedel_fraction_full    0.816
_reflns_Friedel_fraction_max     0.745
_reflns_number_gt                5692
_reflns_number_total             6046
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02980e2.cif
_cod_data_source_block           20230914a_auto
_cod_depositor_comments
'Adding full bibliography for 1574862--1574863.cif.'
_cod_original_cell_volume        3337.95(7)
_cod_database_code               1574863
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1O1
_shelx_estimated_absorpt_t_max   0.833
_shelx_estimated_absorpt_t_min   0.833
_diffrn_oxdiff_digest_frames
;
0118cf19d4e8fb20824f1369474a3497f501118bb31
;
_diffrn_oxdiff_digest_hkl
;
0139452d8053f4b9b37ff417e61afb0f583012
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C21(H21), C22(H22), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C8(H8A,H8B), C9(H9A,H9B), C19(H19A,H19B), C24(H24A,H24B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,
 H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              79130
_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 1.706
_oxdiff_exptl_absorpt_empirical_full_min 0.577