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_4037796
_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         'C19 H17 N3 O4'
_chemical_formula_sum            'C19 H17 N3 O4'
_chemical_formula_weight         351.35
_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   geom
_audit_creation_date             2018-11-05
_audit_creation_method
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.1328(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.75480(16)
_cell_length_b                   7.45702(7)
_cell_length_c                   27.2450(2)
_cell_measurement_reflns_used    19834
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.6350
_cell_measurement_theta_min      5.4140
_cell_volume                     3300.98(5)
_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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  1 omega -116.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -44.0566  -77.0000 -180.0000 102

  2 omega -116.00  -14.00   1.0000    1.0000
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  3 omega -116.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -44.0566  -77.0000   90.0000 102

  4 omega -116.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -44.0566  -77.0000    0.0000 102

  5 omega   21.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0566   38.0000   30.0000 94

  6 omega  -25.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0566  -57.0000 -180.0000 93

  7 omega   34.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   21.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega  -25.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0566  -57.0000  -60.0000 93

 10 omega   36.00  121.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
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 11 omega   78.00  178.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000   30.0000 100

 12 omega   78.00  178.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000  -30.0000 100

 13 omega   78.00  178.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000  -60.0000 100

 14 omega   83.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000  150.0000 94

 15 omega   83.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000    0.0000 94

 16 omega   83.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000 -120.0000 94

 17 omega   78.00  178.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000  120.0000 100

 18 omega   83.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000   60.0000 94

 19 omega   78.00  178.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000    0.0000 100

 20 omega   83.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000   90.0000 94

 21 omega   83.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000  -30.0000 94

 22 omega   79.00  109.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -95.0000 -150.0000 30

 23 omega   84.00  109.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000  120.0000 25

 24 omega  151.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000  120.0000 26

 25 omega   78.00  104.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000 -150.0000 26

 26 omega   84.00  110.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000 -180.0000 26

 27 omega   84.00  170.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000  -60.0000 86

 28 omega   78.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000   90.0000 99

 29 omega   83.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000   30.0000 94

 30 omega  131.00  157.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000   60.0000 26

 31 omega   85.00  112.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   45.0000  150.0000 27

 32 omega   36.00  138.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -77.0000  -90.0000 102

 33 omega   78.00  104.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000  -90.0000 26

 34 omega  127.00  153.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000  -90.0000 26

 35 omega   78.00  172.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000 -180.0000 94

 36 omega   83.00  109.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000 -150.0000 26

 37 omega   78.00  104.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000   60.0000 26

 38 omega   83.00  110.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   61.0000  -90.0000 27

 39 omega   78.00  105.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000 -120.0000 27

 40 omega   78.00  104.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049   77.0000  150.0000 26

 41 omega   37.00  138.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0049  -75.0000  118.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_33      0.0332560000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.837
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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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
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_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.265
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_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0660P)^2^+2.7483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1158
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3159
_reflns_number_total             3424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03402_si_002.cif
_cod_data_source_block           jv-dl4-107a
_cod_original_cell_volume        3300.99(5)
_cod_database_code               4037796
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C15H12N2O4
_reflns_odcompleteness_completeness 99.78
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15), C4(H4), C3(H3), C2(H2), C18(H18), C16(H16), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              25625
_shelx_hkl_checksum              21676
_olex2_date_sample_data_collection 2004-05-08
_olex2_exptl_crystal_mounting_method 'Mounted on a Kyroloop using paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'