N-Acylsaccharins: Stable Electrophilic Amide-Based Acyl Transfer Reagents in Pd-Catalyzed Suzuki–Miyaura Coupling via N–C Cleavage
Liu, Chengwei; Meng, Guangrong; Liu, Yongmei; Liu, Ruzhang; Lalancette, Roger; Szostak, Roman; Szostak, Michal; Organic Letters  (2016) –; doi:10.1021/acs.orglett.6b01836

data_1543883
_publ_section_title
;
 N-Acylsaccharins: Stable Electrophilic Amide-Based Acyl Transfer Reagents
 in Pd-Catalyzed Suzuki--Miyaura Coupling via N--C Cleavage
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.6b01836
_journal_year                    2016
_chemical_formula_sum            'C14 H9 N O4 S'
_chemical_formula_weight         287.28
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0936(6)
_cell_length_b                   10.3894(6)
_cell_length_c                   12.0481(7)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.52
_cell_measurement_theta_min      3.67
_cell_volume                     1263.44(13)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11389
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.455
_diffrn_reflns_theta_min         5.623
_exptl_absorpt_coefficient_mu    2.414
_exptl_absorpt_correction_T_max  0.545
_exptl_absorpt_correction_T_min  0.446
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.218
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.060(5)
_refine_ls_extinction_coef       0.0038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0223
_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^)+(0.0293P)^2^+0.2990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0579
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                2225
_reflns_number_total             2242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01836_si_002.cif
_cod_data_source_block           151112RAL_YL_100K_0m_a
_cod_database_code               1543883
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              40442
_shelx_hkl_checksum              24034