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_4037795
_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 H15 N3 O4'
_chemical_formula_sum            'C18 H15 N3 O4'
_chemical_formula_weight         337.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-12-13
_audit_creation_method
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                82.823(5)
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_cell_angle_gamma                89.820(5)
_cell_formula_units_Z            2
_cell_length_a                   8.3364(6)
_cell_length_b                   8.4830(5)
_cell_length_c                   10.7484(7)
_cell_measurement_reflns_used    2582
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.5560
_cell_measurement_theta_min      4.1270
_cell_volume                     753.01(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
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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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2603
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
  1 omega  -68.00   25.00   1.0000    2.3650
omega____ theta____ kappa____ phi______ frames
    -      -44.0566   57.0000  150.0000 93

  2 omega -112.00  -22.00   1.0000    2.3650
omega____ theta____ kappa____ phi______ frames
    -      -44.0566  -57.0000    0.0000 90

  3 omega  -17.00   63.00   1.0000    2.3650
omega____ theta____ kappa____ phi______ frames
    -       44.0566  -57.0000 -150.0000 80

  4 omega   35.00   69.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -30.0000 -120.0000 34

  5 omega   43.00   69.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -30.0000 -150.0000 26

  6 omega   49.00   75.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -45.0000 -180.0000 26

  7 omega   40.00  136.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -77.0000 -150.0000 96

  8 omega   91.00  117.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049 -125.0000  -30.0000 26

  9 omega   97.00  126.00   1.0000    2.3650
omega____ theta____ kappa____ phi______ frames
    -       44.0566 -178.0000  -30.0000 29

 10 omega   45.00  107.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -95.0000   30.0000 62

 11 omega   50.00  106.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -95.0000  150.0000 56

 12 omega   40.00   69.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -30.0000   60.0000 29

 13 omega   44.00   70.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -45.0000   30.0000 26

 14 omega   37.00   65.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -30.0000   90.0000 28

 15 omega   39.00   65.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -45.0000   60.0000 26

 16 omega   35.00   68.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -30.0000  120.0000 33

 17 omega   37.00   63.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -30.0000  150.0000 26

 18 omega   85.00  172.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049   30.0000   60.0000 87

 19 omega   35.00   60.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -30.0000    0.0000 25

 20 omega   36.00   68.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -30.0000  -60.0000 32

 21 omega   35.00   69.00   1.0000    9.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -30.0000  -90.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1819671000
_diffrn_orient_matrix_UB_12      -0.0211399000
_diffrn_orient_matrix_UB_13      -0.0254658000
_diffrn_orient_matrix_UB_21      0.0114034000
_diffrn_orient_matrix_UB_22      -0.0908557000
_diffrn_orient_matrix_UB_23      0.1325665000
_diffrn_orient_matrix_UB_31      -0.0318062000
_diffrn_orient_matrix_UB_32      -0.1574884000
_diffrn_orient_matrix_UB_33      -0.0520504000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5034
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.583
_diffrn_reflns_theta_min         4.152
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88386
_exptl_absorpt_correction_type   multi-scan
_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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       irregular
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0526P)^2^+0.4070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1439
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2332
_reflns_number_total             2974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03402_si_002.cif
_cod_data_source_block           jv-dl4-151a
_cod_database_code               4037795
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C15 H20 N3 O4'
_reflns_odcompleteness_completeness 99.26
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C11(H11), C1(H1), C2(H2), C12(H12), C5(H5), C4(H4)
;
_shelx_res_checksum              31051
_shelx_hkl_checksum              62174
_olex2_date_sample_data_collection 2018-11-29
_olex2_exptl_crystal_mounting_method 'Mounted on a Kryoloop in paratone oil.'
_olex2_submission_special_instructions 'No special instructions were received'