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_4037799
_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 H17 Cl N2 O2'
_chemical_formula_sum            'C18 H17 Cl N2 O2'
_chemical_formula_weight         328.79
_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             2019-08-13
_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                   13.0647(13)
_cell_length_b                   9.4310(12)
_cell_length_c                   24.873(3)
_cell_measurement_reflns_used    2306
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.1420
_cell_measurement_theta_min      4.8730
_cell_volume                     3064.7(6)
_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      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2603
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
  1 omega   20.00   48.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0566   57.0000  150.0000 28

  2 omega   86.00  113.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0566   57.0000  150.0000 27

  3 omega   44.00   77.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000   30.0000 33

  4 omega   30.00  102.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -95.0000   60.0000 72

  5 omega   40.00   66.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000  -60.0000 26

  6 omega   40.00   71.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -45.0000 -150.0000 31

  7 omega   83.00  178.00   1.0000  300.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000    0.0000 95

  8 omega   54.00   86.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0566  164.0000   12.0000 32

  9 omega   35.00  128.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0566  178.0000   90.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0168998000
_diffrn_orient_matrix_UB_12      0.0075685000
_diffrn_orient_matrix_UB_13      0.0612835000
_diffrn_orient_matrix_UB_21      -0.0400318000
_diffrn_orient_matrix_UB_22      0.1537189000
_diffrn_orient_matrix_UB_23      0.0003459000
_diffrn_orient_matrix_UB_31      -0.1095972000
_diffrn_orient_matrix_UB_32      -0.0546540000
_diffrn_orient_matrix_UB_33      0.0092922000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1214
_diffrn_reflns_av_unetI/netI     0.1177
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7916
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.591
_diffrn_reflns_theta_min         3.554
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.303
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77123
_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    1.425
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.409
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1520
_refine_ls_R_factor_gt           0.1073
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2708
_refine_ls_wR_factor_ref         0.3532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1965
_reflns_number_total             3070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03402_si_002.cif
_cod_data_source_block           jv-dl4-142a
_cod_database_code               4037799
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C20 H20 N2 O2 Cl1'
_reflns_odcompleteness_completeness 99.87
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C2(H2A), C14(H14), C17(H17), C16(H16), C5(H5), C15(H15)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              73714
_shelx_hkl_checksum              50234
_olex2_date_sample_data_collection 2018-11-30
_olex2_exptl_crystal_mounting_method 'Mounted on a Kyroloop using paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'