Stereoselective synthesis of C-glycosides from glycals and organotrifluoroborate salts
Othman, Karwan Abdulmajed; Xiang, Yimin; Wang, Yue; Huang, Nianyu; Wang, Nengzhong; Li, Linxuan; Yao, Hui; Chemical Communications 61 (2025) 7867–7870; doi:10.1039/D5CC00271K

data_7134481
_publ_section_title
;
 Stereoselective synthesis of C-glycosides from glycals and
 organotrifluoroborate salts
;
_journal_issue                   43
_journal_name_full               'Chemical Communications'
_journal_page_first              7867
_journal_page_last               7870
_journal_paper_doi               10.1039/D5CC00271K
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H20 O5, 0.5(H2 O)'
_chemical_formula_sum            'C14 H21 O5.5'
_chemical_formula_weight         277.31
_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             2023-09-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-12-08 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   4.83690(10)
_cell_length_b                   14.8689(3)
_cell_length_c                   37.6287(8)
_cell_measurement_reflns_used    14910
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.8180
_cell_measurement_theta_min      3.1410
_cell_volume                     2706.23(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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    -68.00  31.00   1.00    1.00    --  -40.73  52.00  27.00   99
  2  \w    -34.00  65.00   1.00    1.00    --   40.73 -38.00 150.00   99
  3  \w      1.00  82.00   1.00    1.00    --   40.73 -99.00-150.00   81
  4  \w     23.00  97.00   1.00    1.00    --   40.73-125.00 -60.00   74
  5  \w     94.00 178.00   1.00    1.66    --  107.58 125.00 -60.00   84
  6  \w     75.00 178.00   1.00    1.66    --  107.58  77.00   0.00  103
  7  \w     31.00 140.00   1.00    1.66    --  107.58 -77.00-120.00  109
  8  \w     94.00 178.00   1.00    1.66    --  107.58 125.00-120.00   84
  9  \w     94.00 178.00   1.00    1.66    --  107.58 125.00 -90.00   84
 10  \w     34.00 122.00   1.00    1.66    --  107.58-125.00 120.00   88
 11  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00-180.00  100
 12  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00   0.00  109
 13  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00  90.00  100
 14  \w   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00-120.00   99
 15  \w     79.00 178.00   1.00    1.66    --  107.58  30.00-150.00   99
 16  \w     79.00 178.00   1.00    1.66    --  107.58  30.00 -60.00   99
 17  \w     82.00 178.00   1.00    1.66    --  107.58  45.00  90.00   96
 18  \w     82.00 129.00   1.00    1.66    --  107.58  45.00 150.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1413662000
_diffrn_orient_matrix_UB_12      -0.0472830000
_diffrn_orient_matrix_UB_13      -0.0315806000
_diffrn_orient_matrix_UB_21      -0.1428136000
_diffrn_orient_matrix_UB_22      -0.0889104000
_diffrn_orient_matrix_UB_23      0.0102346000
_diffrn_orient_matrix_UB_31      -0.2470167000
_diffrn_orient_matrix_UB_32      0.0243390000
_diffrn_orient_matrix_UB_33      -0.0239816000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            25257
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.971
_diffrn_reflns_theta_min         2.348
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.7002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                5194
_reflns_number_total             5394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00271k2.cif
_cod_data_source_block           34-2_2
_cod_depositor_comments
'Adding full bibliography for 7134479--7134481.cif.'
_cod_original_formula_sum        'C14 H21 O5.50'
_cod_database_code               7134481
_shelx_shelxl_version_number     2018/3
_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, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O11(H11A,H11B)
2.b Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3A), C4(H4A), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21)
2.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C20(H20A,H20B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C23(H23), C24(H24), C26(H26), C27(H27)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C28(H28A,H28B,H28C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4), O6(H6), O8(H8)
;
_shelx_res_checksum              25967
_shelx_hkl_checksum              3138
_olex2_date_sample_data_collection 2023-09-19
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.758
_oxdiff_exptl_absorpt_empirical_full_min 0.596