Phosphine/Palladium Cooperative Catalysis: (4 + 3) Annulations of Morita-Baylis-Hillman Carbonates and Vinyl Benzoxazinanones.
Wang, Yue; Jia, Siming; Li, Er-Qing; Duan, Zheng; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02349

data_4036099
_publ_section_title
;
 Phosphine/Palladium Cooperative Catalysis: (4 + 3) Annulations of
 Morita-Baylis-Hillman Carbonates and Vinyl Benzoxazinanones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02349
_journal_year                    2019
_chemical_formula_moiety         'C28 H26 N2 O6 S'
_chemical_formula_sum            'C28 H26 N2 O6 S'
_chemical_formula_weight         518.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-15
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Olex2 1.2
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_cell_measurement_temperature    293(2)
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_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)
;
_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 -102.00  -74.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
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  2 omega  -48.00   37.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
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  3 omega -102.00  -36.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -180.0000 66

  4 omega   19.00   77.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 58

  5 omega   59.00   85.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 26

  6 omega    8.00   41.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 33

  7 omega   46.00   75.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 29

  8 omega   19.00   69.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  120.0000 50

  9 omega   57.00  101.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 44

 10 omega   69.00  105.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 36

 11 omega   53.00   85.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 32

 12 omega   38.00   96.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  -58.0000 58

 13 omega   89.00  114.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 25

 14 omega   38.00  105.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 67

 15 omega  102.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 76

 16 omega   81.00  107.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 26

 17 omega   94.00  168.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 74

 18 omega   57.00   89.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 32

 19 omega  117.00  165.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 48

 20 omega   47.00   83.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 36

 21 omega   64.00  128.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 64
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0865538000
_diffrn_orient_matrix_UB_12      -0.0134731000
_diffrn_orient_matrix_UB_13      -0.0906844000
_diffrn_orient_matrix_UB_21      0.0228221000
_diffrn_orient_matrix_UB_22      -0.1112320000
_diffrn_orient_matrix_UB_23      0.0067370000
_diffrn_orient_matrix_UB_31      -0.1031649000
_diffrn_orient_matrix_UB_32      -0.0133020000
_diffrn_orient_matrix_UB_33      0.0354235000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       12
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_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10429
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        67.089
_diffrn_reflns_theta_max         67.089
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_correction_T_min  0.82652
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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            yellow
_exptl_crystal_colour_primary    yellow
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_exptl_crystal_description       prism
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_reflns         4578
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.4967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                3466
_reflns_number_total             4578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02349_si_002.cif
_cod_data_source_block           201804217
_cod_database_code               4036099
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_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. Uiso/Uaniso restraints and constraints
Uanis(C21) \\sim Ueq, Uanis(C21A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C20) = Uanis(C20A)
Uanis(C21) = Uanis(C21A)
3. Others
 Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B), C20A(H20C,H20D)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C14(H14), C15(H15), C17(H17),
 C18(H18), C23(H23), C24(H24), C26(H26), C27(H27)
4.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21A(H21D,H21E,H21F), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'