Tricyclic Imidazolidin-4-ones by Witkop Oxidation of Tetrahydro-β-carbolines.
Leas, Derek Andrew; Dong, Yuxiang; Garrison, Jered C.; Wang, Xiaofang; Ezell, Edward L.; Stack, Douglas Edward; Vennerstrom, Jonathan L.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03402

data_4037794
_publ_section_title
;
 Tricyclic Imidazolidin-4-ones by Witkop Oxidation of
 Tetrahydro-\b-carbolines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03402
_journal_year                    2020
_chemical_formula_moiety         'C18 H22 N2 O2'
_chemical_formula_sum            'C18 H22 He0.25 N2 O2'
_chemical_formula_weight         299.37
_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
_audit_creation_date             2018-12-31
_audit_creation_method
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
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_cell_length_b                   9.1977(2)
_cell_length_c                   13.1980(3)
_cell_measurement_reflns_used    5417
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.9630
_cell_measurement_theta_min      5.8450
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      100
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;
  1 omega  -22.00   72.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -       43.8691  -77.0000   90.0000 94

  2 omega   36.00   68.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
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  3 omega   43.00   69.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -30.0000   90.0000 26

  4 omega   41.00   74.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000   60.0000 33

  5 omega   40.00   65.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000   90.0000 25

  6 omega   31.00   57.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -95.0000   60.0000 26

  7 omega   65.00   96.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -95.0000   60.0000 31

  8 omega   79.00  104.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -95.0000   90.0000 25

  9 omega   38.00   69.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -30.0000  -60.0000 31

 10 omega   47.00  127.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -61.0000  -60.0000 80

 11 omega   97.00  136.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000   45.0000 -180.0000 39

 12 omega   44.00  175.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000    0.0000  -60.0000 131

 13 omega   44.00  104.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -95.0000 -180.0000 60

 14 omega   41.00   73.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000 -120.0000 32

 15 omega   41.00   66.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000 -180.0000 25

 16 omega   37.00   69.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -30.0000  -90.0000 32

 17 omega   30.00  107.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -95.0000  -90.0000 77

 18 omega   29.00   61.00   1.0000    5.4750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -95.0000   90.0000 32

 19 omega  -68.00   24.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -      -43.8691   57.0000    0.0000 92

 20 omega  -74.00  -48.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -      -43.8691  -57.0000 -120.0000 26

 21 omega -112.00  -20.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -      -43.8691  -57.0000 -150.0000 92
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_21      -0.1136127000
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_diffrn_orient_matrix_UB_23      -0.0533490000
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_diffrn_orient_matrix_UB_32      0.1620736000
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_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_theta_max         76.256
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_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.669
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       plate
_exptl_crystal_F_000             642
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.227
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_refine_ls_number_reflns         3192
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_refine_ls_R_factor_gt           0.0487
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+0.6447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1367
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_reflns_number_gt                2774
_reflns_number_total             3192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03402_si_002.cif
_cod_data_source_block           jv-dl4-155a
_cod_original_cell_volume        1547.92(7)
_cod_database_code               4037794
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C20 H22 N2 O2'
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_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
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B),
 C18(H18A,H18B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C4(H4)
;
_shelx_res_checksum              51316
_shelx_hkl_checksum              81850
_olex2_date_sample_data_collection 2018-12-18
_olex2_exptl_crystal_mounting_method 'Mounted in paratone oil on a Kryoloop'
_olex2_submission_special_instructions 'No special instructions were received'