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_7134480
_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         'C15 H14 O2'
_chemical_formula_sum            'C15 H14 O2'
_chemical_formula_weight         226.26
_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     direct
_audit_creation_date             2024-11-22
_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                 91.9801(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.87836(11)
_cell_length_b                   4.91995(6)
_cell_length_c                   21.8073(2)
_cell_measurement_reflns_used    6493
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.7080
_cell_measurement_theta_min      2.0130
_cell_volume                     1166.45(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_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     34.00  68.00   0.50    0.70    --  106.53 -57.00-120.00   68
  2  \w     34.00  60.00   0.50    0.70    --  106.53 -57.00 -90.00   52
  3  \w     34.00  62.00   0.50    0.70    --  106.53 -57.00 -30.00   56
  4  \w     70.00 104.00   0.50    0.70    --  106.53 -77.00   0.00   68
  5  \w     42.00  67.00   0.50    0.70    --  106.53 -57.00  60.00   50
  6  \w     39.00  67.00   0.50    0.70    --  106.53 -57.00 150.00   56
  7  \w     38.00  67.00   0.50    0.70    --  106.53 -57.00 -60.00   58
  8  \w     37.00  68.00   0.50    0.70    --  106.53 -57.00-150.00   62
  9  \w     34.00  62.00   0.50    0.70    --  106.53 -57.00-180.00   56
 10  \w     61.00 101.00   0.50    0.70    --  106.53 -99.00-120.00   80
 11  \w    -23.00  31.00   0.50    0.50    --   48.15 -35.00 -38.00  108
 12  \w    -33.00  25.00   0.50    0.50    --  -48.15  35.00 118.00  116
 13  \w     46.00 119.00   0.50    0.50    --   48.15  35.00 118.00  146
 14  \w    119.00 145.00   0.50    0.70    --  106.53  35.00 118.00   52
 15  \w    -39.00   2.00   0.50    0.50    --  -48.15  38.00 -90.00   82
 16  \w    -63.00 -32.00   0.50    0.70    -- -104.00  57.00-120.00   62
 17  \w    -64.00 -39.00   0.50    0.70    -- -104.00  57.00 -90.00   50
 18  \w    -63.00 -33.00   0.50    0.70    -- -104.00  57.00 -30.00   60
 19  \w    -64.00 -35.00   0.50    0.70    -- -104.00  57.00  60.00   58
 20  \w    -62.00 -32.00   0.50    0.70    -- -104.00  57.00 120.00   60
 21  \w   -168.00 -93.00   0.50    0.70    -- -104.00 -19.00  30.00  150
 22  \w   -173.00-101.00   0.50    0.70    -- -104.00 -35.00 -38.00  144
 23  \w   -119.00 -37.00   0.50    0.50    --  -48.15 -35.00 -38.00  164
;
_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      0.1157795000
_diffrn_orient_matrix_UB_12      -0.1080346000
_diffrn_orient_matrix_UB_13      -0.0306422000
_diffrn_orient_matrix_UB_21      -0.0795421000
_diffrn_orient_matrix_UB_22      -0.0915711000
_diffrn_orient_matrix_UB_23      -0.0560714000
_diffrn_orient_matrix_UB_31      0.0186156000
_diffrn_orient_matrix_UB_32      0.2791967000
_diffrn_orient_matrix_UB_33      -0.0302661000
_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7566
_diffrn_reflns_point_group_measured_fraction_full 0.730
_diffrn_reflns_point_group_measured_fraction_max 0.682
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.161
_diffrn_reflns_theta_min         2.027
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
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    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 711 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_coef       0.0109(12)
_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   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0844P)^2^+0.0938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.275
_reflns_Friedel_fraction_full    0.384
_reflns_Friedel_fraction_max     0.334
_reflns_number_gt                3230
_reflns_number_total             3375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00271k2.cif
_cod_data_source_block           2023-77
_cod_depositor_comments
'Adding full bibliography for 7134479--7134481.cif.'
_cod_database_code               7134480
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C26(H26), C29(H29)
1.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C30(H30A,H30B)
1.c 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),
  C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
 C27(H27), C28(H28)
1.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_res_checksum              13334
_shelx_hkl_checksum              82363
_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 3.887
_oxdiff_exptl_absorpt_empirical_full_min 0.309