Cu(i)-Catalyzed amidation/imidation of N-arylglycine ester derivatives via C–N coupling under mild conditions
Daggupati, Ramana V.; Malapaka, Chandrasekharam; Organic Chemistry Frontiers 5 (2018) 788–; doi:10.1039/C7QO00851A

data_1553916
_publ_section_title
;
 Cu(i)-Catalyzed amidation/imidation of N-arylglycine ester derivatives
 via C--N coupling under mild conditions
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              788
_journal_paper_doi               10.1039/C7QO00851A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C17 H13 Cl N2 O4'
_chemical_formula_sum            'C17 H13 Cl N2 O4'
_chemical_formula_weight         344.76
_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_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-09-26 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                119.490(7)
_cell_angle_beta                 102.929(6)
_cell_angle_gamma                92.342(5)
_cell_formula_units_Z            4
_cell_length_a                   10.1754(7)
_cell_length_b                   13.7004(8)
_cell_length_c                   13.8309(10)
_cell_measurement_reflns_used    4820
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.7930
_cell_measurement_theta_min      3.7190
_cell_volume                     1609.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9929
_diffrn_measured_fraction_theta_max 0.9739
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -14.00  21.00   1.00    1.00    --    0.00 -57.00 -60.00   35
  2  \w    -16.00  86.00   1.00    1.00    --   54.00 -77.00 -30.00  102
  3  \w     87.00 129.00   1.00    1.00    --  108.00 -50.00   0.00   42
  4  \w     69.00 112.00   1.00    1.00    --  108.00-111.00 120.00   43
  5  \w     39.00 108.00   1.00    1.00    --   54.00-125.00 150.00   69
  6  \w     41.00 138.00   1.00    1.00    --  108.00 -77.00 120.00   97
  7  \w     52.00 115.00   1.00    1.00    --  108.00-111.00 -60.00   63
  8  \w    102.00 129.00   1.00    1.00    --  108.00 -50.00-120.00   27
  9  \w     60.00  99.00   1.00    1.00    --  108.00-111.00-120.00   39
 10  \w     46.00  85.00   1.00    1.00    --  108.00 -77.00 -60.00   39
 11  \w     38.00 125.00   1.00    1.00    --  108.00 -38.00-150.00   87
 12  \w     77.00 103.00   1.00    1.00    --   54.00  57.00 -30.00   26
 13  \w     77.00 154.00   1.00    1.00    --  108.00  77.00  30.00   77
 14  \w     58.00 134.00   1.00    1.00    --  108.00 178.00 120.00   76
 15  \w     25.00  62.00   1.00    1.00    --    0.00  57.00  90.00   37
 16  \w     21.00  76.00   1.00    1.00    --   54.00 -57.00-150.00   55
 17  \w      6.00  46.00   1.00    1.00    --   54.00 -99.00-120.00   40
 18  \w    -18.00 100.00   1.00    1.00    --   54.00 -19.00   0.00  118
 19  \w     38.00 134.00   1.00    1.00    --  108.00 -38.00  90.00   96
 20  \w     34.00 175.00   1.00    1.00    --  108.00   0.00   0.00  141
 21  \w    139.00 167.00   1.00    1.00    --  108.00 111.00-180.00   28
 22  \w     62.00 148.00   1.00    1.00    --  108.00 178.00-180.00   86
 23  \w     36.00 119.00   1.00    1.00    --   54.00  57.00-180.00   83
 24  \w    -20.00  16.00   1.00    1.00    --    0.00  57.00  90.00   36
 25  \w    -51.00 -23.00   1.00    1.00    --    0.00 -57.00 -60.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0030138000
_diffrn_orient_matrix_UB_12      0.0028020000
_diffrn_orient_matrix_UB_13      0.1121998000
_diffrn_orient_matrix_UB_21      0.1200036000
_diffrn_orient_matrix_UB_22      -0.0660719000
_diffrn_orient_matrix_UB_23      -0.0090289000
_diffrn_orient_matrix_UB_31      0.1025163000
_diffrn_orient_matrix_UB_32      0.1134065000
_diffrn_orient_matrix_UB_33      0.0714263000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10894
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         70.11
_diffrn_reflns_theta_min         3.74
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.321
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.4225
_exptl_crystal_description       needle
_exptl_crystal_F_000             715.7827
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.3298
_refine_diff_density_min         -0.5072
_refine_diff_density_rms         0.0523
_refine_ls_d_res_high            0.8199
_refine_ls_d_res_low             11.8211
_refine_ls_goodness_of_fit_ref   1.1456
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1456
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1676
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -16
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4808
_reflns_number_total             5964
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7qo00851a2.cif
_cod_data_source_block           exp_8662
_cod_database_code               1553916
_chemical_oxdiff_formula         'C20 H20 O'
_reflns_odcompleteness_completeness 99.88
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C26(H26)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), C16(H16), C17(H17), C5(H5), C13(H13), C30(H30), C29(H29),
 C33(H33), C32(H32), C8(H8), C7(H7), C23(H23), C14(H14), C6(H6), C22(H22),
 C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C28(H28a,H28b,H28c)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.835