Highly regioselective and stereoselective synthesis of C-Aryl glycosides <i>via</i> nickel-catalyzed <i>ortho</i>-C-H glycosylation of 8-aminoquinoline benzamides.
Shi, Wei-Yu; Ding, Ya-Nan; Zheng, Nian; Gou, Xue-Ya; Zhang, Zhe; Chen, Xi; Luan, Yu-Yong; Niu, Zhi-Jie; Liang, Yong-Min; Chemical communications (Cambridge, England) 57 (2021) 8945–8948; doi:10.1039/d1cc03589d

data_7128758
_publ_section_title
;
 Highly regioselective and stereoselective synthesis of C-Aryl glycosides
 <i>via</i> nickel-catalyzed <i>ortho</i>-C-H glycosylation of
 8-aminoquinoline benzamides.
;
_journal_issue                   71
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8945
_journal_page_last               8948
_journal_paper_doi               10.1039/d1cc03589d
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H29 I N2 O6'
_chemical_formula_sum            'C28 H29 I N2 O6'
_chemical_formula_weight         616.43
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-05-28 deposited with the CCDC.	2021-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.68300(10)
_cell_length_b                   11.68300(10)
_cell_length_c                   39.0801(3)
_cell_measurement_reflns_used    21452
_cell_measurement_temperature    301.00(10)
_cell_measurement_theta_max      76.3190
_cell_measurement_theta_min      3.9390
_cell_volume                     5334.14(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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     92.00 121.00   0.50    0.23    --  104.25  30.00  30.00   58
  2  \w     99.00 144.00   0.50    0.23    --  104.25  45.00 100.00   90
  3  \w    150.00 175.00   0.50    0.23    --  104.25  45.00 100.00   50
  4  \w     91.00 117.00   0.50    0.14    --   46.32 148.00 -33.00   52
  5  \w     94.00 177.00   0.50    0.23    --  104.25  30.00-180.00  166
  6  \w     36.00  61.00   0.50    0.23    --  104.25 -77.00 -60.00   50
  7  \w     43.00  70.00   0.50    0.23    --  104.25 -61.00-150.00   54
  8  \w     32.00  65.00   0.50    0.23    --  104.25 -61.00 -60.00   66
  9  \w     73.00 104.00   0.50    0.23    --  104.25 -77.00 -60.00   62
 10  \w     44.00  70.00   0.50    0.23    --  104.25 -61.00  90.00   52
 11  \w    -25.00  66.00   0.50    0.14    --   46.32 -76.00 153.00  182
 12  \w    -26.00  14.00   0.50    0.14    --   46.32 -19.00 150.00   80
 13  \w   -118.00 -90.00   0.50    0.23    -- -102.00 -45.00  30.00   56
 14  \w   -174.00 -82.00   0.50    0.23    -- -102.00-123.00  82.00  184
 15  \w   -119.00 -94.00   0.50    0.14    --  -46.32-125.00  30.00   50
 16  \w   -100.00 -74.00   0.50    0.14    --  -46.32-125.00 -90.00   52
 17  \w   -171.00-135.00   0.50    0.23    -- -102.00 -45.00  30.00   72
 18  \w    -96.00 -71.00   0.50    0.23    -- -102.00 125.00 150.00   50
 19  \w    -54.00 -29.00   0.50    0.23    -- -102.00 125.00 150.00   50
 20  \w    -16.00  29.00   0.50    0.14    --  -46.32  19.00 -90.00   90
 21  \w    -80.00 -35.00   0.50    0.23    -- -102.00  77.00-180.00   90
 22  \w    -81.00 -55.00   0.50    0.23    -- -102.00  76.00 -80.00   52
 23  \w    -69.00 -30.00   0.50    0.23    -- -102.00  61.00 120.00   78
 24  \w    -65.00 -35.00   0.50    0.23    -- -102.00  61.00 150.00   60
 25  \w     34.00  83.00   0.50    0.23    --  104.25-123.00  82.00   98
;
_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      0.0662355000
_diffrn_orient_matrix_UB_12      -0.0718892000
_diffrn_orient_matrix_UB_13      0.0264474000
_diffrn_orient_matrix_UB_21      0.0316155000
_diffrn_orient_matrix_UB_22      0.1098416000
_diffrn_orient_matrix_UB_23      0.0196145000
_diffrn_orient_matrix_UB_31      -0.1095954000
_diffrn_orient_matrix_UB_32      -0.0117158000
_diffrn_orient_matrix_UB_33      0.0216910000
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            36485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.564
_diffrn_reflns_theta_min         3.949
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       block
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1958 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+1.0567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0627
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                5145
_reflns_number_total             5511
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03589d2.cif
_cod_data_source_block           shiweiyu_0525-1_auto
_cod_depositor_comments          'Adding full bibliography for 7128758.cif.'
_cod_original_cell_volume        5334.14(10)
_cod_database_code               7128758
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.695
_shelx_estimated_absorpt_t_min   0.507
_reflns_odcompleteness_completeness 99.97
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13),
 C15(H15)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
;
_shelx_res_checksum              85450
_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 1.923
_oxdiff_exptl_absorpt_empirical_full_min 0.710