Catalytic Ynamide Oxidation Strategy for the Preparation of α-Functionalized Amides
Pan, Fei; Li, Xin-Ling; Chen, Xiu-Mei; Shu, Chao; Ruan, Peng-Peng; Shen, Cang-Hai; Lu, Xin; Ye, Long-Wu; ACS Catalysis 6 (2016) 6055–; doi:10.1021/acscatal.6b01599

data_4513934
_publ_section_title
;
 Catalytic Ynamide Oxidation Strategy for the Preparation of
 \a-Functionalized Amides
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              6055
_journal_paper_doi               10.1021/acscatal.6b01599
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C22 H18 N2 O4 S2'
_chemical_formula_sum            'C22 H18 N2 O4 S2'
_chemical_formula_weight         438.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.31(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.653(4)
_cell_length_b                   12.700(3)
_cell_length_c                   9.4888(19)
_cell_measurement_reflns_used    11836
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.21
_cell_volume                     2123.8(8)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1194
_diffrn_reflns_av_unetI/netI     0.1445
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11836
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.21
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1650
_refine_ls_R_factor_gt           0.0873
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1854P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2359
_refine_ls_wR_factor_ref         0.3512
_reflns_number_gt                1549
_reflns_number_total             3502
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs6b01599_si_002.cif
_cod_data_source_block           p
_cod_depositor_comments          'Adding full bibliography for 4513934.cif.'
_cod_original_cell_volume        2123.7(7)
_cod_database_code               4513934
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Me refined with riding coordinates:
 C41(H41A,H41B,H41C)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C32(H32), C33(H33), C35(H35), C36(H36)
;
_olex2_submission_special_instructions 'No special instructions were received'