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_7160077
_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         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-01-29 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.208(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8803(10)
_cell_length_b                   13.7121(9)
_cell_length_c                   8.2130(5)
_cell_measurement_reflns_used    4711
_cell_measurement_temperature    248(50)
_cell_measurement_theta_max      30.0990
_cell_measurement_theta_min      3.7440
_cell_volume                     1515.35(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      248(50)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.819
_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    -60.00   7.00   0.50   31.67    --    3.35 -36.00 -75.00  134
  2  \w      0.00  70.00   0.50   31.67    --    3.35  36.00  80.00  140
  3  \w    -17.00  19.00   0.50   31.67    --   -3.98  77.00 -60.00   72
  4  \w     -6.00  27.00   0.50   31.67    --   -3.98 -99.00 -30.00   66
  5  \w    -25.00   2.00   0.50   31.67    --   -3.98  77.00  90.00   54
  6  \w    -23.00   5.00   0.50   31.67    --   -3.98  77.00-120.00   56
  7  \w    -27.00  18.00   0.50   31.67    --   -3.98  77.00 150.00   90
;
_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      -0.0367950000
_diffrn_orient_matrix_UB_12      -0.0237283000
_diffrn_orient_matrix_UB_13      0.0322425000
_diffrn_orient_matrix_UB_21      0.0335431000
_diffrn_orient_matrix_UB_22      -0.0023585000
_diffrn_orient_matrix_UB_23      0.0804144000
_diffrn_orient_matrix_UB_31      -0.0173096000
_diffrn_orient_matrix_UB_32      0.0458955000
_diffrn_orient_matrix_UB_33      0.0207847000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14346
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.132
_diffrn_reflns_theta_min         3.335
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0533P)^2^+0.1540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1252
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2428
_reflns_number_total             3667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00800f2.cif
_cod_data_source_block           nks-ckj-420(a)
_cod_depositor_comments
'Adding full bibliography for 7160076--7160081.cif.'
_cod_database_code               7160077
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C68 H64 N8 O12 '
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.999
_diffrn_oxdiff_digest_frames
;
01e3172aa315766ee2e3e380e12caae8fa00025c825
;
_diffrn_oxdiff_digest_hkl
;
01c26d0cd56c4973b969add3ae14b3357bfb6b
;
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C17(H17), C13(H13), C5(H5), C4(H4), C14(H14),
 C15(H15), C16(H16), C7(H7), C6(H6)
;
_shelx_res_checksum              54121
_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 1.513
_oxdiff_exptl_absorpt_empirical_full_min 0.718