Palladium-catalyzed C(carbonyl)-C bond cleavage of amides: a facile access to phenylcarbamate derivatives with alcohols.
Yan, Xufei; Sun, Huihui; Xiang, Haifeng; Yu, Da-Gang; Luo, Daibing; Zhou, Xiangge; Chemical communications (Cambridge, England) 54 (2018) 8606–8609; doi:10.1039/c8cc03954b

data_7121948
_publ_section_title
;
 Palladium-catalyzed C(carbonyl)-C bond cleavage of amides: a facile
 access to phenylcarbamate derivatives with alcohols.
;
_journal_issue                   62
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8606
_journal_page_last               8609
_journal_paper_doi               10.1039/c8cc03954b
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C22 H22 N2 O Pd S'
_chemical_formula_sum            'C22 H22 N2 O Pd S'
_chemical_formula_weight         468.87
_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
_audit_creation_date             2018-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-07 deposited with the CCDC.
2018-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4594(3)
_cell_length_b                   11.2077(4)
_cell_length_c                   19.4065(6)
_cell_measurement_reflns_used    3427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1250
_cell_measurement_theta_min      3.5100
_cell_volume                     2057.44(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -52.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -38.0000   30.0000 65

  2 omega  -22.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -99.0000    0.0000 78

  3 omega  -19.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1231  -99.0000 -150.0000 43

  4 omega   -2.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419   38.0000  150.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0049680000
_diffrn_orient_matrix_UB_12      -0.0594741000
_diffrn_orient_matrix_UB_13      0.0124030000
_diffrn_orient_matrix_UB_21      0.0331344000
_diffrn_orient_matrix_UB_22      -0.0208552000
_diffrn_orient_matrix_UB_23      -0.0305013000
_diffrn_orient_matrix_UB_31      0.0670302000
_diffrn_orient_matrix_UB_32      0.0060346000
_diffrn_orient_matrix_UB_33      0.0158831000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10241
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.007
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.032(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0361P)^2^+0.7184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                3256
_reflns_number_total             4056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03954b2.cif
_cod_data_source_block           180307_s4_yxf
_cod_depositor_comments
'Adding full bibliography for 7121947--7121948.cif.'
_cod_database_code               7121948
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3s1pd1
_shelx_estimated_absorpt_t_max   0.785
_shelx_estimated_absorpt_t_min   0.717
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'