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_7160081
_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_formula_moiety         'C11 H12 N O3 Pd0.5'
_chemical_formula_sum            'C11 H12 N O3 Pd0.5'
_chemical_formula_weight         259.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-27 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.300(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4678(9)
_cell_length_b                   5.0155(3)
_cell_length_c                   17.0923(10)
_cell_measurement_reflns_used    4206
_cell_measurement_temperature    270(3)
_cell_measurement_theta_max      75.1010
_cell_measurement_theta_min      3.6290
_cell_volume                     1075.68(13)
_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      270(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.951
_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    -50.00  24.00   0.50    0.24    --  -38.50  57.00 142.00  148
  2  \w   -101.00 -27.00   0.50    0.24    --  -38.50 -57.00   0.00  148
  3  \w    -14.00  61.00   0.50    0.24    --   49.06 -57.00   0.00  150
  4  \w     38.00 112.00   0.50    0.24    --   49.06  57.00 142.00  148
  5  \w     40.00 114.00   0.50    0.85    --  102.63 -57.00   0.00  148
  6  \w     91.00 166.00   0.50    0.85    --  102.63  57.00 142.00  150
  7  \w    -86.00  -6.00   0.50    0.24    --  -38.50 125.00 -90.00  160
  8  \w   -105.00 -35.00   0.50    0.24    --  -38.50 -37.00-180.00  140
  9  \w   -105.00 -35.00   0.50    0.24    --  -38.50 -37.00 150.00  140
 10  \w     40.00 116.00   0.50    0.85    --  102.63 -61.00  90.00  152
 11  \w     34.00 111.00   0.50    0.85    --  102.63 -15.00 -60.00  154
 12  \w     95.00 171.00   0.50    0.85    --  102.63  15.00  60.00  152
 13  \w    103.00 167.00   0.50    0.85    --  102.63  77.00-120.00  128
 14  \w     38.00 107.00   0.50    0.85    --  102.63 -45.00 150.00  138
 15  \w     38.00 112.00   0.50    0.85    --  102.63-125.00-150.00  148
 16  \w     97.00 168.00   0.50    0.85    --  102.63 125.00 -30.00  142
 17  \w   -101.00 -27.00   0.50    0.24    --  -38.50 -57.00 -90.00  148
 18  \w     38.00 112.00   0.50    0.24    --   49.06  57.00 -30.00  148
 19  \w     38.00 112.00   0.50    0.24    --   49.06  57.00  60.00  148
;
_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      0.0644046000
_diffrn_orient_matrix_UB_12      0.0602912000
_diffrn_orient_matrix_UB_13      -0.0562593000
_diffrn_orient_matrix_UB_21      0.0688315000
_diffrn_orient_matrix_UB_22      0.2004234000
_diffrn_orient_matrix_UB_23      0.0656466000
_diffrn_orient_matrix_UB_31      0.0786370000
_diffrn_orient_matrix_UB_32      -0.2247470000
_diffrn_orient_matrix_UB_33      0.0434559000
_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  0.1131
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8238
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.723
_diffrn_reflns_theta_min         3.607
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27910
_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 reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         1.535
_refine_diff_density_min         -1.500
_refine_diff_density_rms         0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0756
_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^)+(0.1539P)^2^+0.1352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2096
_refine_ls_wR_factor_ref         0.2286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1546
_reflns_number_total             2126
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00800f2.cif
_cod_data_source_block           nks-ckj-tr-g-pd_auto
_cod_depositor_comments
'Adding full bibliography for 7160076--7160081.cif.'
_cod_original_cell_volume        1075.68(12)
_cod_original_formula_sum        'C11 H12 N O3 Pd0.50'
_cod_database_code               7160081
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N  O Pd'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.930
_reflns_odcompleteness_completeness 99.81
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              79273
_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 2.841
_oxdiff_exptl_absorpt_empirical_full_min 0.317