Anomeric oxyacetamide assisted site-selective C-2 arylation and its application in <i>O</i>/<i>S</i> glycosylation of 2,3 eno-pyranoside.
Zargar, Irshad Ahmad; Rasool, Bisma; Bappa, S. K.; Mukherjee, Debaraj; Chemical communications (Cambridge, England) 60 (2024) 13040–13043; doi:10.1039/d4cc04301d

data_7133887
_publ_section_title
;
 Anomeric oxyacetamide assisted site-selective C-2 arylation and its
 application in <i>O</i>/<i>S</i> glycosylation of 2,3 eno-pyranoside.
;
_journal_issue                   89
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13040
_journal_page_last               13043
_journal_paper_doi               10.1039/d4cc04301d
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ,
_chemical_formula_sum            'C2.4 H2.67 F0.13 N0.13 O0.93'
_chemical_formula_weight         50.85
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-08-16 deposited with the CCDC.	2024-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            30
_cell_length_a                   5.1122(10)
_cell_length_b                   13.527(3)
_cell_length_c                   26.011(6)
_cell_measurement_reflns_used    9655
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      2.79
_cell_volume                     1798.7(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            42680
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.116
_diffrn_reflns_theta_max         25.116
_diffrn_reflns_theta_min         2.172
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            ,
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       ,
_exptl_crystal_F_000             800
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1246 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0442P)^2^+0.2839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0735
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3123
_reflns_number_total             3191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04301d2.cif
_cod_data_source_block           mo_IRSHAD_IIIM_0m_a
_cod_depositor_comments          'Adding full bibliography for 7133887.cif.'
_cod_original_formula_sum        'C2.40 H2.67 F0.13 N0.13 O0.93'
_cod_database_code               7133887
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              86943
_shelx_hkl_checksum              74275