A facile approach to β-amino acid derivatives via palladium-catalyzed hydrocarboxylation of enimides with formic acid.
Dai, Jie; Ren, Wenlong; Wang, Haining; Shi, Yian; Organic & biomolecular chemistry 13 (2015) 8429–8432; doi:10.1039/c5ob01304f

data_7154587
_publ_section_title
;
 A facile approach to \b-amino acid derivatives via palladium-catalyzed
 hydrocarboxylation of enimides with formic acid.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8429
_journal_page_last               8432
_journal_paper_doi               10.1039/c5ob01304f
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C11 H9 N O4'
_chemical_formula_sum            'C11 H9 N O4'
_chemical_formula_weight         219.19
_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_creation_date             2015-02-12
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_audit_update_record
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2015-06-13 deposited with the CCDC.
2015-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                80.505(11)
_cell_angle_beta                 76.238(11)
_cell_angle_gamma                65.983(9)
_cell_formula_units_Z            4
_cell_length_a                   8.629(2)
_cell_length_b                   10.440(3)
_cell_length_c                   12.379(4)
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_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4838
_cell_measurement_theta_min      1.6987
_cell_volume                     986.5(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
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'SHELXT (Sheldrick, 2014)'
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_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 40.0487
              2theta: -20.2261
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 40.0487
              2theta: -20.2261
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_diffrn_measurement_device
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Saturn724+ (2x2 bin mode)
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_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
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_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0146
_diffrn_orient_matrix_UB_12      -0.0727
_diffrn_orient_matrix_UB_13      -0.1058
_diffrn_orient_matrix_UB_21      0.0809
_diffrn_orient_matrix_UB_22      -0.0090
_diffrn_orient_matrix_UB_23      0.0667
_diffrn_orient_matrix_UB_31      -0.0510
_diffrn_orient_matrix_UB_32      -0.0481
_diffrn_orient_matrix_UB_33      0.0452
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8415
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.630
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0511P)^2^+0.3765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4015
_reflns_number_total             4432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01304f2.cif
_cod_data_source_block           sa3944
_cod_depositor_comments          'Adding full bibliography for 7154587.cif.'
_cod_database_code               7154587
_diffrn_number_total             4433
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C9A(H9AA,H9AB), C10A(H10C,H10D)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C5(H5), C6(H6), C3A(H3A), C4A(H4AB), C5A(H5A), C6A(H6A)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O4A(H4AA)
;
_shelx_res_checksum              98099
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'