Non-benzenoid <i>N</i>-aryl oxalamide: synthesis of troponyl-oxalamide peptides by Pd(II)-catalyzed C(sp<sup>3</sup>)-H functionalization of glycinamides.
Jena, Chinmay K.; Sharma, Nagendra K.; Organic & biomolecular chemistry 22 (2024) 6822–6832; doi:10.1039/d4ob00800f

data_7160080
_publ_section_title
;
 Non-benzenoid <i>N</i>-aryl oxalamide: synthesis of troponyl-oxalamide
 peptides by Pd(II)-catalyzed C(sp<sup>3</sup>)-H functionalization of
 glycinamides.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6822
_journal_page_last               6832
_journal_paper_doi               10.1039/d4ob00800f
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration s
_chemical_formula_moiety         '2(C13 H14 N2 O5)'
_chemical_formula_sum            'C26 H28 N4 O10'
_chemical_formula_weight         556.52
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-01-29 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0174(2)
_cell_length_b                   19.6228(4)
_cell_length_c                   19.9031(5)
_cell_measurement_reflns_used    6005
_cell_measurement_temperature    193(14)
_cell_measurement_theta_max      74.8620
_cell_measurement_theta_min      4.4360
_cell_volume                     2740.68(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      193(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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    -45.00  31.00   0.50    0.21    --  -38.50  17.00 118.00  152
  2  \w    103.00 171.00   0.50    1.60    --  102.63 110.00-117.00  136
  3  \w     33.00 110.00   0.50    1.60    --  102.63 -17.00 -50.00  154
  4  \w     97.00 167.00   0.50    1.60    --  102.63 126.00 -35.00  140
  5  \w    -42.00  28.00   0.50    0.21    --  -38.50  37.00   0.00  140
  6  \w    -17.00  52.00   0.50    0.21    --   49.06 -37.00  90.00  138
  7  \w    -17.00  52.00   0.50    0.21    --   49.06 -37.00 150.00  138
  8  \w     42.00  82.00   0.50    1.60    --  102.63 -30.00-120.00   80
  9  \w     41.00 103.00   0.50    1.60    --  102.63 -94.00 150.00  124
 10  \w    123.00 154.00   0.50    1.60    --  102.63  45.00 150.00   62
 11  \w    104.00 137.00   0.50    1.60    --  102.63  77.00  60.00   66
 12  \w     39.00  96.00   0.50    1.60    --  102.63-125.00-150.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0406358000
_diffrn_orient_matrix_UB_12      0.0738483000
_diffrn_orient_matrix_UB_13      0.0219364000
_diffrn_orient_matrix_UB_21      0.0268012000
_diffrn_orient_matrix_UB_22      0.0207606000
_diffrn_orient_matrix_UB_23      -0.0740532000
_diffrn_orient_matrix_UB_31      -0.2141435000
_diffrn_orient_matrix_UB_32      0.0166155000
_diffrn_orient_matrix_UB_33      -0.0050480000
_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  0.0389
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12621
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.584
_diffrn_reflns_theta_min         4.443
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1458 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0597P)^2^+0.1825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_full    0.852
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                4385
_reflns_number_total             5077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00800f2.cif
_cod_data_source_block           nks-ckj-1030a_auto
_cod_depositor_comments
'Adding full bibliography for 7160076--7160081.cif.'
_cod_database_code               7160080
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.991
_reflns_odcompleteness_completeness 99.79
_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:
 C10(H10), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3A), N2(H2), N4(H4A), C3(H3), C16(H16), C4(H4), C5(H5), C6(H6),
 C17(H17), C7(H7), C18(H18), C20(H20), C19(H19)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C)
;
_shelx_res_checksum              19286
_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 1.405
_oxdiff_exptl_absorpt_empirical_full_min 0.640