Palladium Catalyzed C-H Glycosylation and Retro Diels-Alder Tandem Reaction via Structurally Modified Norbornadiene (smNBDs)
An, Yang; Zhang, Bo-Sheng; Ding, Ya-Nan; Zhang, Zhe; Gou, Xue-Ya; Li, Xue-Song; Wang, Xiaolei; Li, Yuke; Liang, Yong-Min; Chemical Science  (2021) –; doi:10.1039/D1SC03569J

data_1564494
_publ_section_title
;
 Palladium Catalyzed C-H Glycosylation and Retro Diels-Alder Tandem
 Reaction via Structurally Modified Norbornadiene (smNBDs)
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03569J
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H33 N O5'
_chemical_formula_sum            'C24 H33 N O5'
_chemical_formula_weight         415.51
_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             2020-09-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-12-03 deposited with the CCDC.	2021-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.361(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3272(3)
_cell_length_b                   10.7693(3)
_cell_length_c                   12.3819(3)
_cell_measurement_reflns_used    5782
_cell_measurement_temperature    225(50)
_cell_measurement_theta_max      69.9320
_cell_measurement_theta_min      10.2710
_cell_volume                     1180.41(6)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      225(50)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  24.00   1.00    1.00    --    0.00 -42.00  57.00   96
  2  \w    -30.00  70.00   1.00    1.00    --    0.00  77.00  30.00  100
  3  \w    -54.00   2.00   1.00    1.00    --    0.00 120.00 -83.00   56
  4  \w     10.00 127.00   1.00    1.00    --   54.00  19.00 -30.00  117
  5  \w      1.00  96.00   1.00    1.00    --   54.00 -99.00 -60.00   95
  6  \w     33.00 123.00   1.00    1.00    --   54.00  57.00  30.00   90
  7  \w     33.00 123.00   1.00    1.00    --   54.00  57.00  90.00   90
  8  \w    -15.00  75.00   1.00    1.00    --   54.00 -57.00  60.00   90
  9  \w      1.00  96.00   1.00    1.00    --   54.00 -99.00-180.00   95
 10  \w    -15.00  75.00   1.00    1.00    --   54.00 -57.00 -30.00   90
 11  \w     38.00 130.00   1.00    2.00    --  108.00 -50.00 -90.00   92
 12  \w     36.00 146.00   1.00    2.00    --  108.00 -91.00-150.00  110
 13  \w     38.00 130.00   1.00    2.00    --  108.00 -50.00-150.00   92
 14  \w     36.00 134.00   1.00    2.00    --  108.00 -38.00-180.00   98
 15  \w     36.00 146.00   1.00    2.00    --  108.00 -91.00  60.00  110
 16  \w     86.00 178.00   1.00    2.00    --  108.00  50.00-120.00   92
 17  \w    100.00 178.00   1.00    2.00    --  108.00 111.00-150.00   78
 18  \w     35.00 142.00   1.00    2.00    --  108.00 -25.00 120.00  107
 19  \w     36.00 116.00   1.00    2.00    --  108.00-111.00 150.00   80
 20  \w     35.00 178.00   1.00    2.00    --  108.00   0.00  30.00  143
 21  \w     36.00 134.00   1.00    2.00    --  108.00 -38.00  60.00   98
 22  \w    100.00 178.00   1.00    2.00    --  108.00 111.00-180.00   78
 23  \w     36.00 116.00   1.00    2.00    --  108.00-111.00  30.00   80
 24  \w    -69.00  21.00   1.00    1.00    --    0.00 -57.00 -30.00   90
 25  \w    -75.00 -17.00   1.00    1.00    --    0.00 154.00  74.00   58
 26  \w     33.00 123.00   1.00    1.00    --   54.00  57.00-180.00   90
 27  \w     24.00 124.00   1.00    1.00    --   54.00  77.00 120.00  100
 28  \w     24.00 124.00   1.00    1.00    --   54.00  77.00 -60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1436113000
_diffrn_orient_matrix_UB_12      0.0792185000
_diffrn_orient_matrix_UB_13      -0.0478724000
_diffrn_orient_matrix_UB_21      0.0904559000
_diffrn_orient_matrix_UB_22      0.1175762000
_diffrn_orient_matrix_UB_23      0.0504441000
_diffrn_orient_matrix_UB_31      0.0382474000
_diffrn_orient_matrix_UB_32      0.0192371000
_diffrn_orient_matrix_UB_33      -0.1111492000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12480
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.577
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         3.761
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75715
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4124
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0548P)^2^+0.0712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3878
_reflns_number_total             4124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03569j2.cif
_cod_data_source_block           anyang_0917
_cod_original_cell_volume        1180.42(6)
_cod_database_code               1564494
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 99.91
_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,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H18A(0.75) H18B(0.75) H18C(0.25) H18D(0.25) O3(0.75) O3B(0.25)
3.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18(H18C,H18D)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              62982
_shelx_hkl_checksum              89312
_olex2_date_sample_data_collection 2020-09-18
_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 1.486
_oxdiff_exptl_absorpt_empirical_full_min 0.660