Iron-catalyzed oxidative cleavage of C-N bonds of tertiary amines: syntheses of unsymmetrical ureas from isocyanates.
Aizezi, Bumairemu; Yusan, Bulunuer; Sun, Pinchang; Wusiman, Abudureheman; Organic & biomolecular chemistry 24 (2026) 905–910; doi:10.1039/d5ob01697e

data_7161022
_publ_section_title
;
 Iron-catalyzed oxidative cleavage of C-N bonds of tertiary amines:
 syntheses of unsymmetrical ureas from isocyanates.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              905
_journal_page_last               910
_journal_paper_doi               10.1039/d5ob01697e
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C15 H15 N3 O3'
_chemical_formula_sum            'C15 H15 N3 O3'
_chemical_formula_weight         285.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-12-16
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-10-22 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.5017(9)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   15.38200(14)
_cell_length_b                   20.5919(2)
_cell_length_c                   17.87192(16)
_cell_measurement_reflns_used    16398
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.8310
_cell_measurement_theta_min      4.9880
_cell_volume                     5598.63(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.957
_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     55.00 101.00   0.50    0.05    --   62.22  15.00 150.00   92
  2  \w     58.00  84.00   0.50    0.05    --   62.22  15.00 120.00   52
  3  \w     62.00 100.00   0.50    0.05    --   62.22  15.00  90.00   76
  4  \w     77.00 104.00   0.50    0.05    --   74.32  15.00  60.00   54
  5  \w     78.00 109.00   0.50    0.05    --   71.28  15.00  90.00   62
  6  \w     61.00  95.00   0.50    0.05    --   62.22  15.00  60.00   68
  7  \w     56.00  82.00   0.50    0.05    --   62.22  15.00   0.00   52
  8  \w     76.00 115.00   0.50    0.05    --   74.32  15.00   0.00   78
  9  \w     72.00  97.00   0.50    0.05    --   74.32  15.00 -60.00   50
 10  \w     68.00 102.00   0.50    0.05    --   74.32  15.00 -90.00   68
 11  \w     79.00 115.00   0.50    0.05    --   74.32  15.00-150.00   72
 12  \w     55.00  82.00   0.50    0.05    --   62.22  15.00-150.00   54
 13  \w     25.00  73.00   0.50    0.05    --   62.22-125.00 -60.00   96
 14  \w     25.00  70.00   0.50    0.05    --   62.22-125.00-120.00   90
 15  \w     48.00  75.00   0.50    0.05    --   62.22-125.00   0.00   54
 16  \w     27.00  77.00   0.50    0.05    --   62.22-125.00  30.00  100
 17  \w     47.00  78.00   0.50    0.05    --   62.22-125.00  60.00   62
 18  \w     35.00  87.00   0.50    0.05    --   71.28-125.00  30.00  104
 19  \w     50.00  76.00   0.50    0.05    --   71.28-125.00  60.00   52
 20  \w     46.00  76.00   0.50    0.05    --   62.22-125.00  90.00   60
 21  \w     32.00  60.00   0.50    0.05    --   62.22-125.00 120.00   56
 22  \w     39.00  70.00   0.50    0.05    --   74.32-125.00 120.00   62
 23  \w     65.00  90.00   0.50    0.05    --   74.32-125.00  90.00   50
 24  \w     45.00  88.00   0.50    0.05    --   74.32-125.00  60.00   86
 25  \w     65.00  90.00   0.50    0.05    --   74.32-125.00  30.00   50
 26  \w     45.00  90.00   0.50    0.05    --   74.32-125.00   0.00   90
 27  \w     57.00  83.00   0.50    0.05    --   74.32-125.00 -30.00   52
 28  \w     38.00  64.00   0.50    0.05    --   74.32-125.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0291746000
_diffrn_orient_matrix_UB_12      -0.0710113000
_diffrn_orient_matrix_UB_13      0.0149376000
_diffrn_orient_matrix_UB_21      0.0818167000
_diffrn_orient_matrix_UB_22      0.0125030000
_diffrn_orient_matrix_UB_23      -0.0383365000
_diffrn_orient_matrix_UB_31      0.0521266000
_diffrn_orient_matrix_UB_32      0.0200207000
_diffrn_orient_matrix_UB_33      0.0767673000
_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  0.0162
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21901
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.973
_diffrn_reflns_theta_min         3.612
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       needle
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+2.7614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4857
_reflns_number_total             5361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01697e2.cif
_cod_data_source_block           244579
_cod_original_cell_volume        5598.64(9)
_cod_database_code               7161022
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14),
 C17(H17), C18(H18), C20(H20), C21(H21), C25(H25), C26(H26), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              95541
_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 1.310
_oxdiff_exptl_absorpt_empirical_full_min 0.817