Switchable synthesis of benzimidazole/quinoxaline <i>C</i>-glycosides with <i>o</i>-phenylenediamines and sulfoxonium ylide glyco-reagents.
Liu, Deng-Yin; Hu, Xin-Yue; Zhang, Cong-Zhen; Wen, Miao-Miao; Ren, Xiao-Xi; Liu, Xu-Ge; Chemical communications (Cambridge, England) 61 (2025) 12131–12134; doi:10.1039/d5cc02719e

data_7134814
_publ_section_title
;
 Switchable synthesis of benzimidazole/quinoxaline <i>C</i>-glycosides
 with <i>o</i>-phenylenediamines and sulfoxonium ylide glyco-reagents.
;
_journal_issue                   65
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12131
_journal_page_last               12134
_journal_paper_doi               10.1039/d5cc02719e
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H22 N2 O5'
_chemical_formula_sum            'C18 H22 N2 O5'
_chemical_formula_weight         346.37
_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             2023-07-25
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-02-18 deposited with the CCDC.	2025-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.207(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1504(4)
_cell_length_b                   19.6553(6)
_cell_length_c                   9.7569(4)
_cell_measurement_reflns_used    2890
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      71.5360
_cell_measurement_theta_min      4.4890
_cell_volume                     1715.14(12)
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(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 0.972
_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    -72.00  34.00   1.00    1.04    --  -40.73  77.00  60.00  106
  2  \w   -109.00 -18.00   1.00    1.04    --  -40.73 -57.00 150.00   91
  3  \w     81.00 178.00   1.00    1.50    --  106.95  30.00  90.00   97
  4  \w    101.00 167.00   1.00    1.50    --  106.95 125.00   0.00   66
  5  \w     58.00  86.00   1.00    1.50    --  106.95 -45.00 150.00   28
  6  \w     90.00 133.00   1.00    1.50    --  106.95 -45.00 150.00   43
  7  \w     28.00 108.00   1.00    1.50    --  106.95 -94.00 -30.00   80
  8  \w     64.00  94.00   1.00    1.50    --  106.95 -77.00-120.00   30
  9  \w     51.00  91.00   1.00    1.04    --   40.73-125.00-180.00   40
 10  \w     32.00 121.00   1.00    1.50    --  106.95 -30.00 -90.00   89
;
_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      -0.0289298000
_diffrn_orient_matrix_UB_12      -0.0341055000
_diffrn_orient_matrix_UB_13      -0.1453898000
_diffrn_orient_matrix_UB_21      -0.1485930000
_diffrn_orient_matrix_UB_22      -0.0289960000
_diffrn_orient_matrix_UB_23      0.0251680000
_diffrn_orient_matrix_UB_31      -0.0822399000
_diffrn_orient_matrix_UB_32      0.0643399000
_diffrn_orient_matrix_UB_33      -0.0656450000
_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  0.0472
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6872
_diffrn_reflns_point_group_measured_fraction_full 0.730
_diffrn_reflns_point_group_measured_fraction_max 0.695
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.200
_diffrn_reflns_theta_min         4.499
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59560
_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            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         4797
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0661P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1319
_reflns_Friedel_coverage         0.388
_reflns_Friedel_fraction_full    0.442
_reflns_Friedel_fraction_max     0.400
_reflns_number_gt                4285
_reflns_number_total             4797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02719e2.cif
_cod_data_source_block           2431
_cod_depositor_comments          'Adding full bibliography for 7134814.cif.'
_cod_original_cell_volume        1715.15(11)
_cod_database_code               7134814
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C26(H26), C27(H27), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3A), C5(H5), C36(H36), N3(H3), C20(H20), C21(H21),
 C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C35(H35A,
 H35B,H35C)
;
_shelx_res_checksum              108
_shelx_hkl_checksum              715
_olex2_date_sample_data_collection 2023-07-24
_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 1.645
_oxdiff_exptl_absorpt_empirical_full_min 0.634