Asymmetric α,γ-Regioselective [3 + 3] Formal Cycloadditions of α,β-Unsaturated Aldehydes via Cascade Dienamine-Dienamine Catalysis.
Xiao, Wei; Yin, Xiang; Zhou, Zhi; Du, Wei; Chen, Ying-Chun; Organic letters 18 (2016) 116–119; doi:10.1021/acs.orglett.5b03355

data_1540692
_publ_section_title
;
 Asymmetric \a,\g-Regioselective [3 + 3] Formal Cycloadditions of
 \a,\b-Unsaturated Aldehydes via Cascade Dienamine-Dienamine Catalysis.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              116
_journal_page_last               119
_journal_paper_doi               10.1021/acs.orglett.5b03355
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C12 H13 N O4'
_chemical_formula_sum            'C12 H13 N O4'
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_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-01-15
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Olex2 1.2
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_cell_angle_alpha                90
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_cell_length_b                   8.94615(12)
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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  1 omega    1.00   76.00   1.0000    1.0000
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  2 omega   55.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega    1.00   76.00   1.0000    1.0000
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  4 omega   18.00  106.00   1.0000    1.0000
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  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   20.00  104.00   1.0000    1.0000
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  7 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   18.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -57.0000 -120.0000 84

 10 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 12 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 13 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega   90.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega   39.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega  101.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  112.0000  120.0000 77

 18 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   91.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   39.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000    0.0000 78

 22 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 23 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 24 omega   70.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  120.0000 108

 25 omega   39.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  150.0000 71

 26 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 27 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000   90.0000 94

 28 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000 -120.0000 84

 29 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  -30.0000 94

 30 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -57.0000   30.0000 84

 31 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000    0.0000 94

 32 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 33 omega   81.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 34 omega   81.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 35 omega   87.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 25
;
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_diffrn_orient_matrix_UB_33      -0.0300551000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
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_diffrn_source                   'sealed X-ray tube'
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light colourless'
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;
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 Flack x determined using 1295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
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_refine_ls_extinction_method     none
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0564P)^2^+0.0376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_data_source_file            ol5b03355_si_002.cif
_cod_data_source_block           4l
_cod_depositor_comments
;
         Adding full bibliography for 1540692.cif.

2019-02-25
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C12 H13 N O4)'
_cod_original_formula_sum        'C24 H26 N2 O8'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     473.47
_cod_database_code               1540692
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C19(H19), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C23(H23A,H23B), C20(H20A,H20B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C15(H15), C32(H32), C28(H28), C26(H26), C10(H10), C27(H27)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'