Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp3)–H bonds of aliphatic amine substrates
Wang, Chao; Zhang, Li; Chen, Changpeng; Han, Jian; Yao, Yingming; Zhao, Yingsheng; Chem. Sci. 6 (2015) 4610–; doi:10.1039/C5SC00519A

data_1519764
_publ_section_title
;
 Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via
 carbonylation of \g-C(sp3)--H bonds of aliphatic amine substrates
;
_journal_issue                   8
_journal_name_full               'Chem. Sci.'
_journal_page_first              4610
_journal_paper_doi               10.1039/C5SC00519A
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C15 H22 N2 O5'
_chemical_formula_sum            'C15 H22 N2 O5'
_chemical_formula_weight         310.34
_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             2014-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-02-10 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7542(4)
_cell_length_b                   11.2346(6)
_cell_length_c                   13.4066(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1619.77(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5351
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_min         3.031
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 820 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0430P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                2379
_reflns_number_total             2841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc00519a3.cif
_cod_data_source_block           g141128d
_cod_depositor_comments          'Adding full bibliography for 1519764.cif.'
_cod_original_cell_volume        1619.78(13)
_cod_database_code               1519764
_shelxl_version_number           2014/6
_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 Ternary CH refined with riding coordinates:
 C1(H1), C10(H10), C2(H2), C4(H4), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C7(H7A,H7B,
 H7C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              47766
_shelx_hkl_checksum              10104
_olex2_submission_special_instructions 'No special instructions were received'