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_4037798
_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         'C15 H18 N2 O2'
_chemical_formula_sum            'C15 H18 N2 O2'
_chemical_formula_weight         258.31
_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
_audit_creation_date             2019-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7991(5)
_cell_length_b                   11.9747(5)
_cell_length_c                   19.5546(10)
_cell_measurement_reflns_used    4990
_cell_measurement_temperature    120
_cell_measurement_theta_max      75.5580
_cell_measurement_theta_min      4.4470
_cell_volume                     2528.7(2)
_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
;
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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2603
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega -111.00  -30.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      -43.8691  -38.0000  -30.0000 81

  2 omega -113.00  -22.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      -43.8691  -38.0000 -120.0000 91

  3 omega  -94.00  -66.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      -43.8691 -153.0000   25.0000 28

  4 omega   36.00   68.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -30.0000    0.0000 32

  5 omega   36.00   69.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -30.0000  -30.0000 33

  6 omega   49.00   95.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -95.0000  -30.0000 46

  7 omega   36.00   69.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -30.0000   30.0000 33

  8 omega   49.00   77.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000   60.0000 28

  9 omega   37.00   69.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -30.0000 -150.0000 32

 10 omega   43.00   77.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000  120.0000 34

 11 omega   37.00   69.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -30.0000  -60.0000 32

 12 omega   49.00   77.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000 -120.0000 28

 13 omega   36.00   64.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -30.0000   90.0000 28

 14 omega   40.00   76.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000  -90.0000 36

 15 omega   87.00  126.00   1.0000   26.6750
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -61.0000  150.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1008268000
_diffrn_orient_matrix_UB_12      0.0222081000
_diffrn_orient_matrix_UB_13      0.0541059000
_diffrn_orient_matrix_UB_21      0.0889846000
_diffrn_orient_matrix_UB_22      -0.0397560000
_diffrn_orient_matrix_UB_23      0.0566954000
_diffrn_orient_matrix_UB_31      0.0479629000
_diffrn_orient_matrix_UB_32      0.1200883000
_diffrn_orient_matrix_UB_33      0.0086983000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9489
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.319
_diffrn_reflns_theta_min         4.522
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62196
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0938P)^2^+0.8736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2364
_reflns_number_total             2605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03402_si_002.cif
_cod_data_source_block           jv-dl5-010a
_cod_database_code               4037798
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C15H18N2O2
_reflns_odcompleteness_completeness 99.96
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              97757
_shelx_hkl_checksum              79180
_olex2_date_sample_data_collection 2019-03-21
_olex2_exptl_crystal_mounting_method 'Mounted on a Kryoloop using paratone oil.'
_olex2_submission_special_instructions 'No special instructions were received'