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_7121947
_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         'C19 H23 N O3 S'
_chemical_formula_sum            'C19 H23 N O3 S'
_chemical_formula_weight         345.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc1zb4r6
_audit_creation_date             2016-06-23
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-03-02 deposited with the CCDC.
2018-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                78.594(5)
_cell_angle_beta                 69.193(5)
_cell_angle_gamma                70.534(6)
_cell_formula_units_Z            2
_cell_length_a                   9.1466(5)
_cell_length_b                   10.0450(6)
_cell_length_c                   11.2749(6)
_cell_measurement_reflns_used    4808
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2950
_cell_measurement_theta_min      4.6450
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_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
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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)'
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_diffrn_ambient_temperature      293(2)
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;
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omega____ theta____ kappa____ phi______ frames
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  2 omega   23.00   90.00   1.0000    1.0600
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  3 omega  -31.00   63.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
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  4 omega   20.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000    0.0000 84

  5 omega   23.00   90.00   1.0000    1.0600
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  6 omega  -31.00   53.00   1.0000    1.0600
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  7 omega   20.00  104.00   1.0000    1.0600
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  8 omega  -33.00   55.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
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  9 omega   23.00   90.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -120.0000 67

 10 omega   38.00   91.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
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 11 omega   38.00   91.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 12 omega   38.00  116.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 78

 13 omega   39.00  109.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 14 omega   39.00  109.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 15 omega   38.00  116.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 16 omega   40.00   98.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 17 omega   90.00  175.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 85

 18 omega   70.00  178.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 108

 19 omega   38.00   91.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 20 omega   38.00   91.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
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 21 omega   40.00  135.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 95

 22 omega   38.00   91.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 23 omega   40.00  135.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 95

 24 omega   91.00  176.00   1.0000    4.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

 25 omega   20.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84

 26 omega  -31.00   53.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   30.0000 84

 27 omega   10.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -30.0000 94

 28 omega   10.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -180.0000 94

 29 omega   10.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   60.0000 94

 30 omega   10.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -120.0000 94

 31 omega   20.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -90.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1182619000
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_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0288
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_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_number            10019
_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_min         4.212
_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67133
_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_colour            'clear light colourless'
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_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0837
_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^)+(0.1428P)^2^+0.6853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2340
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_reflns_number_gt                3220
_reflns_number_total             3541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03954b2.cif
_cod_data_source_block           zxg-yan
_cod_depositor_comments
'Adding full bibliography for 7121947--7121948.cif.'
_cod_original_cell_volume        909.28(10)
_cod_database_code               7121947
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C00J, C00L
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C00N, C00O
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C00J \\sim C00L: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.001
C00N \\sim C00O: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.001
4.a Secondary CH2 refined with riding coordinates:
 C00O(H00U,H00V)
4.b Aromatic/amide H refined with riding coordinates:
 N004(H004), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I)
4.c Idealised Me refined as rotating group:
 C00K(H00A,H00J,H00K), C00L(H00L,H00M,H00N), C00M(H00O,H00P,H00Q), C00N(H00R,
 H00S,H00T)
;
_shelx_res_checksum              71625
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-22
_olex2_submission_special_instructions 'No special instructions were received'