Transient imine as a directing group for the Pd-catalyzed anomeric C(sp<sup>3</sup>)-H arylation of 3-aminosugars.
Ghouilem, Juba; Bazzi, Sokna; Grimblat, Nicolas; Retailleau, Pascal; Gandon, Vincent; Messaoudi, Samir; Chemical communications (Cambridge, England) 59 (2023) 2497–2500; doi:10.1039/d3cc00046j

data_7131268
_publ_section_title
;
 Transient imine as a directing group for the Pd-catalyzed anomeric
 C(sp<sup>3</sup>)-H arylation of 3-aminosugars.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2497
_journal_page_last               2500
_journal_paper_doi               10.1039/d3cc00046j
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H29 N3 O3'
_chemical_formula_sum            'C27 H29 N3 O3'
_chemical_formula_weight         443.53
_chemical_name_systematic
2R,3S,4S,6S)-4-azido-3-(benzyloxy)-2-((benzyloxy)methyl)-6-(p-tolyl)tetrahydro-2H-pyran
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-12-08 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9654(3)
_cell_length_b                   10.7233(8)
_cell_length_c                   44.847(3)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0
_cell_measurement_theta_min      6.9
_cell_volume                     2387.9(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device
'four-circle partial \c goniometer diffractometer'
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  'Confocal Osmic mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_av_unetI/netI     0.0858
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            21847
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        65.083
_diffrn_reflns_theta_max         65.083
_diffrn_reflns_theta_min         7.223
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku micromax 007 1.2kW'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Abscor (Rigaku,1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       stick
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: deuterated chloroform'
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     183
_refine_ls_restrained_S_all      0.810
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0489P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1855
_reflns_number_total             4045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00046j2.cif
_cod_data_source_block           JG-SArN3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7131267--7131268.cif.
;
_cod_database_code               7131268
_shelx_res_checksum              92964
_shelx_hkl_checksum              205