DBU-mediated synthesis of amides from carbodiimides and unstrained 1,3-diketones
Qin, Chang-Qing; Liu, Xin-Ni; Gu, Man-Zhen; Xu, Yi-Bing; Chen, Guo-Shu; Liu, Yun-Lin; New Journal of Chemistry 49 (2025) 366–370; doi:10.1039/D4NJ04537H

data_1573395
_publ_section_title
;
 DBU-mediated synthesis of amides from carbodiimides and unstrained
 1,3-diketones
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              366
_journal_page_last               370
_journal_paper_doi               10.1039/D4NJ04537H
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C14 H13 N O'
_chemical_formula_sum            'C14 H13 N O'
_chemical_formula_weight         211.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-10-14 deposited with the CCDC.	2024-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1158(10)
_cell_length_b                   9.8374(13)
_cell_length_c                   25.365(3)
_cell_measurement_reflns_used    3294
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      70.0740
_cell_measurement_theta_min      3.4330
_cell_volume                     2274.6(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.946
_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     55.00  89.00   0.50    0.50    --   42.30  57.00-120.00   68
  2  \w     81.00 112.00   0.50    0.50    --   42.30  77.00 150.00   62
  3  \w     94.00 132.00   0.50    0.50    --   42.30  57.00-120.00   76
  4  \w     24.00  50.00   0.50    0.50    --   42.30  57.00-120.00   52
  5  \w     80.00 132.00   0.50    0.50    --   42.30  77.00 -90.00  104
  6  \w     98.00 131.00   0.50    0.50    --   42.30  77.00   0.00   66
  7  \w     69.00 128.00   0.50    0.50    --  101.00 -63.00  60.00  118
  8  \w    139.00 175.00   0.50    0.50    --  101.00  82.00 120.00   72
  9  \w    118.00 177.00   0.50    0.50    --  101.00  82.00-120.00  118
 10  \w     40.00  66.00   0.50    0.50    --  101.00 -63.00  60.00   52
 11  \w     71.00 130.00   0.50    0.50    --  101.00  50.00 -60.00  118
 12  \w     90.00 122.00   0.50    0.50    --  101.00  82.00 120.00   64
 13  \w     12.00 140.00   0.50    0.50    --  101.00 -82.00  60.00  256
 14  \w    -23.00  80.00   0.50    0.50    --   42.10 -82.00 -30.00  206
 15  \w     -6.00  58.00   0.50    0.50    --   42.10 -57.00 -30.00  128
 16  \w    -11.00  49.00   0.50    0.50    --   42.10 -82.00 120.00  120
 17  \w     21.00  67.00   0.50    0.50    --   42.10 -57.00  90.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0761053000
_diffrn_orient_matrix_UB_12      -0.1034195000
_diffrn_orient_matrix_UB_13      0.0362206000
_diffrn_orient_matrix_UB_21      0.1069933000
_diffrn_orient_matrix_UB_22      -0.0368388000
_diffrn_orient_matrix_UB_23      -0.0449241000
_diffrn_orient_matrix_UB_31      0.1062973000
_diffrn_orient_matrix_UB_32      0.1114364000
_diffrn_orient_matrix_UB_33      0.0192302000
_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  0.0704
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7979
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.190
_diffrn_reflns_theta_min         3.485
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0771
_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^)+(0.1718P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2090
_refine_ls_wR_factor_ref         0.2623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1400
_reflns_number_total             2090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj04537h2.cif
_cod_data_source_block           621-01
_cod_depositor_comments          'Adding full bibliography for 1573395.cif.'
_cod_database_code               1573395
_shelx_shelxl_version_number     2018/3
_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 Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C9(H9), C10(H10), C3(H3), C2(H2), C14(H14), C13(H13),
 C1(H1A)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              90851
_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 3.688
_oxdiff_exptl_absorpt_empirical_full_min 0.464