Cascade Oxidative Coupling/Cyclization: A Gateway to 3-Amino Polysubstituted Five-Membered Heterocycles.
Li, Kaizhi; You, Jingsong; The Journal of organic chemistry 81 (2016) 2327–2339; doi:10.1021/acs.joc.5b02838

data_4036582
_publ_section_title
;
 Cascade Oxidative Coupling/Cyclization: A Gateway to 3-Amino
 Polysubstituted Five-Membered Heterocycles.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2327
_journal_page_last               2339
_journal_paper_doi               10.1021/acs.joc.5b02838
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C26 H23 N3 O3'
_chemical_formula_sum            'C26 H23 N3 O3'
_chemical_formula_weight         425.47
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-30
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_length_c                   11.0491(4)
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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)
;
_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)
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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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;
  1 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000   60.0000 84

  2 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000 -120.0000 84

  3 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000 -180.0000 66

  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000   90.0000 84

  5 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000 -150.0000 88

  6 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000   60.0000 74

  7 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  -30.0000 95

  8 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  -90.0000 95

  9 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  -60.0000 66

 10 omega   40.00   98.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 11 omega  100.00  178.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 78

 12 omega   38.00   91.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 13 omega   40.00   98.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 14 omega   38.00  116.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

 15 omega   91.00  176.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 16 omega  100.00  178.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

 17 omega   38.00   91.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 18 omega   38.00  116.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 19 omega   70.00  178.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 108

 20 omega   41.00  126.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 85

 21 omega   39.00  109.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 22 omega   38.00   91.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 23 omega   38.00   91.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 24 omega   39.00  109.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 25 omega   41.00  126.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 85

 26 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  -30.0000 84

 27 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000  120.0000 88

 28 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000 -180.0000 95

 29 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000  -30.0000 88

 30 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000  150.0000 88

 31 omega  -35.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -19.0000  -60.0000 100

 32 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  -90.0000 84

 33 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -90.0000 84

 34 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000   60.0000 95

 35 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000   90.0000 95

 36 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000    0.0000 84

 37 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000   30.0000 84

 38 omega   91.00  176.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 85

 39 omega   87.00  178.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

 40 omega   70.00  178.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 108

 41 omega   81.00  176.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 42 omega   81.00  176.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 43 omega   81.00  176.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 44 omega   81.00  176.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 95

 45 omega   81.00  176.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 46 omega   81.00  176.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 47 omega   87.00  178.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 91

 48 omega   91.00  176.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85
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_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0164
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_process_details
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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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
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_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
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_exptl_crystal_description
;
;
_exptl_crystal_F_000             448
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_refine_ls_extinction_method     none
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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^)+(0.0940P)^2^+0.1843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           lkz0529
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00O(H00I,H00N)
2.b Aromatic/amide H refined with riding coordinates:
 N005(H005), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W)
2.c Idealised Me refined as rotating group:
 C00I(H00A,H00B,H00C), C00N(H00D,H00E,H00F)
;
_shelx_res_checksum              90372
_shelx_hkl_checksum              50314
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-05-29
_olex2_submission_special_instructions 'No special instructions were received'