α-Regioselective Asymmetric [3 + 2] Annulations of Morita-Baylis-Hillman Carbonates with Cyclic 1-Azadienes and Mechanism Elucidation.
Wang, Kai-Kai; Jin, Tian; Huang, Xin; Ouyang, Qin; Du, Wei; Chen, Ying-Chun; Organic letters 18 (2016) 872–875; doi:10.1021/acs.orglett.6b00189

data_1542640
_publ_section_title
;
 \a-Regioselective Asymmetric [3 + 2] Annulations of Morita-Baylis-Hillman
 Carbonates with Cyclic 1-Azadienes and Mechanism Elucidation.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              872
_journal_page_last               875
_journal_paper_doi               10.1021/acs.orglett.6b00189
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C28 H22 N2 O5 S'
_chemical_formula_sum            'C28 H22 N2 O5 S'
_chemical_formula_weight         498.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-09-15
_audit_creation_method
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Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                111.2004(17)
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_cell_formula_units_Z            2
_cell_length_a                   8.28533(15)
_cell_length_b                   11.53237(19)
_cell_length_c                   14.1641(3)
_cell_measurement_reflns_used    16326
_cell_measurement_temperature    290.70(10)
_cell_measurement_theta_max      71.3240
_cell_measurement_theta_min      6.0290
_cell_volume                     1252.27(4)
_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
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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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_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  -32.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000    0.0000 94

  4 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   55.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   57.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  178.0000    0.0000 52

 10 omega   57.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  178.0000 -120.0000 52

 11 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 12 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 13 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 14 omega   39.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000   60.0000 71

 15 omega   40.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 16 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 17 omega   40.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 18 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   38.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   91.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   44.0000  158.0000 86

 21 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85

 22 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 23 omega   39.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000 -150.0000 71

 24 omega   40.00  135.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 95

 25 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 26 omega   41.00  126.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 85

 27 omega   39.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  -30.0000 71

 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000 -180.0000 94

 29 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  -60.0000 94

 30 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000  -90.0000 84

 31 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  120.0000 94

 32 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000 -150.0000 94

 33 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000    0.0000 84

 34 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -57.0000   60.0000 84

 35 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -99.0000    0.0000 75

 36 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

 37 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 85

 38 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 39 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 91

 40 omega   90.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 85

 41 omega   90.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 85

 42 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 91

 43 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

 44 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 45 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 91

 46 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 91

 47 omega   90.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

 48 omega   81.00  155.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 74

 49 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95
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_diffrn_orient_matrix_UB_31      -0.0601507000
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_diffrn_orient_matrix_UB_33      0.0974137000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0161
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_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.538
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_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
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_exptl_absorpt_correction_type   multi-scan
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
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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^)+(0.0514P)^2^+0.2714P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                4605
_reflns_number_total             4829
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           3a'
_cod_database_code               1542640
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 H1 N1 O1 S1'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C11(H11), C6(H6), C3(H3), C15(H15), C25(H25), C19(H19), C26(H26),
 C4(H4), C16(H16), C5(H5), C24(H24), C18(H18), C17(H17)
2.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              62250
_shelx_hkl_checksum              9881
_olex2_submission_special_instructions 'No special instructions were received'