Intramolecular Pd-Catalyzed Anomeric C(sp(3))-H Activation of Glycosyl Carboxamides.
Probst, Nicolas; Grelier, Gwendal; Ghermani, NourEddine; Gandon, Vincent; Alami, Mouâd; Messaoudi, Samir; Organic letters 19 (2017) 5038–5041; doi:10.1021/acs.orglett.7b02170

data_1547164
_publ_section_title
;
 Intramolecular Pd-Catalyzed Anomeric C(sp(3))-H Activation of Glycosyl
 Carboxamides.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5038
_journal_page_last               5041
_journal_paper_doi               10.1021/acs.orglett.7b02170
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration PARSON
_chemical_formula_sum            'C21 H20 F3 N O9'
_chemical_formula_weight         487.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.837(8)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   65.689(8)
_cell_length_b                   4.6345(5)
_cell_length_c                   21.077(2)
_cell_measurement_reflns_used    26995
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      0.5960
_cell_measurement_theta_min      0.0261
_cell_volume                     6302.2(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      303(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'BRUKER D8'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1935
_diffrn_reflns_av_unetI/netI     0.2560
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       72
_diffrn_reflns_limit_h_min       -78
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26995
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        66.765
_diffrn_reflns_theta_max         66.764
_diffrn_reflns_theta_min         2.309
_diffrn_source                   tube
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'SADABS (Version 2.10). George Sheldrick, University of G&#x00F6;ttingen, 2003.'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       block
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details
;
 Flack x determined using 998 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     876
_refine_ls_number_reflns         10780
_refine_ls_number_restraints     816
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.2266
_refine_ls_R_factor_gt           0.1107
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1062P)^2^+9.7393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2366
_refine_ls_wR_factor_ref         0.2972
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                4762
_reflns_number_total             10780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02170_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 1547164.cif.'
_cod_original_cell_volume        6302.1(12)
_cod_database_code               1547164
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.802
_shelx_estimated_absorpt_t_max   0.893
_shelx_res_checksum              77566
_shelx_hkl_checksum              47819