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_7134479
_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 unk
_chemical_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-09
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-11-22 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.239(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6971(6)
_cell_length_b                   5.8730(4)
_cell_length_c                   12.5155(9)
_cell_measurement_reflns_used    4164
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.9450
_cell_measurement_theta_min      6.0060
_cell_volume                     637.52(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.975
_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    -27.00  31.00   0.50    0.50    --    0.00 -82.00 -90.00  116
  2  \w      2.00  31.00   0.50    0.50    --    0.00 -82.00   0.00   58
  3  \w    -45.00   0.00   0.50    0.50    --    0.00 -77.00  60.00   90
  4  \w     80.00 152.00   0.50    0.50    --   95.80  30.00  90.00  144
  5  \w     83.00 126.00   0.50    0.50    --   95.80 -82.00  30.00   86
  6  \w     25.00 105.00   0.50    0.50    --   95.80 -30.00-120.00  160
  7  \w     73.00 160.00   0.50    0.50    --   95.80  61.00-180.00  174
  8  \w      7.00  48.00   0.50    0.50    --   95.80 -82.00  30.00   82
  9  \w     79.00 145.00   0.50    0.50    --   95.80  30.00-180.00  132
 10  \w    155.00 180.00   0.50    0.50    --   95.80  82.00-120.00   50
 11  \w     90.00 145.00   0.50    0.50    --   95.80  30.00 120.00  110
 12  \w    160.00 185.00   0.50    0.50    --   95.80  30.00  30.00   50
 13  \w    -26.00  24.00   0.50    0.50    --    0.00 -82.00 150.00  100
 14  \w    -25.00   1.00   0.50    0.50    --    0.00 -82.00-180.00   52
 15  \w    -27.00  -2.00   0.50    0.50    --    0.00 -82.00 -30.00   50
 16  \w     10.00  53.00   0.50    0.50    --   95.80 -15.00  60.00   86
 17  \w    136.00 172.00   0.50    0.50    --   95.80  82.00 -30.00   72
 18  \w     72.00  98.00   0.50    0.50    --   95.80  61.00 120.00   52
 19  \w     87.00 113.00   0.50    0.50    --   95.80  82.00 -30.00   52
 20  \w     81.00 107.00   0.50    0.50    --   95.80 -61.00  60.00   52
 21  \w     94.00 129.00   0.50    0.50    --   95.80  45.00-150.00   70
 22  \w    146.00 182.00   0.50    0.50    --   95.80  45.00-150.00   72
 23  \w     27.00  53.00   0.50    0.50    --   95.80 -77.00 -60.00   52
 24  \w     82.00 120.00   0.50    0.50    --   95.80 -77.00 -60.00   76
 25  \w     39.00  65.00   0.50    0.50    --   95.80 -61.00  60.00   52
 26  \w     73.00  86.50   0.50    0.50    --   95.80  61.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0127613000
_diffrn_orient_matrix_UB_12      0.1123121000
_diffrn_orient_matrix_UB_13      -0.1101957000
_diffrn_orient_matrix_UB_21      0.1716480000
_diffrn_orient_matrix_UB_22      -0.0661579000
_diffrn_orient_matrix_UB_23      0.0035794000
_diffrn_orient_matrix_UB_31      -0.0437238000
_diffrn_orient_matrix_UB_32      -0.2276666000
_diffrn_orient_matrix_UB_33      -0.0555230000
_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  0.1154
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4254
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.296
_diffrn_reflns_theta_min         5.099
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       0.056(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2230
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0580
_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^)+(0.1389P)^2^+0.0169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1576
_reflns_Friedel_coverage         0.597
_reflns_Friedel_fraction_full    0.769
_reflns_Friedel_fraction_max     0.715
_reflns_number_gt                2161
_reflns_number_total             2230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00271k2.cif
_cod_data_source_block           2023-11
_cod_depositor_comments
'Adding full bibliography for 7134479--7134481.cif.'
_cod_database_code               7134479
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C32 H32 O4 '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              6945
_shelx_hkl_checksum              33970
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.291
_oxdiff_exptl_absorpt_empirical_full_min 0.510