Direct Sulfide-Catalyzed Diastereoselective [4+1] Annulations of ortho-Quinone Methides and Bromides.
Liu, Yan-Qing; Li, Qing-Zhu; Zhu, Hong-Ping; Feng, Xin; Peng, Cheng; Huang, Wei; Li, Jun-Long; Han, Bo; The Journal of organic chemistry 83 (2018) 12753–12762; doi:10.1021/acs.joc.8b02189

data_4035398
_publ_section_title
;
 Direct Sulfide-Catalyzed Diastereoselective [4+1] Annulations of
 ortho-Quinone Methides and Bromides.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12753
_journal_page_last               12762
_journal_paper_doi               10.1021/acs.joc.8b02189
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C24 H18 O4'
_chemical_formula_sum            'C24 H18 O4'
_chemical_formula_weight         370.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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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)
;
_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)
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_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.3500
omega____ theta____ kappa____ phi______ frames
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  2 omega  -31.00   63.00   1.0000    1.3500
omega____ theta____ kappa____ phi______ frames
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  3 omega    9.00  104.00   1.0000    1.3500
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  -90.0000 95

  4 omega  -31.00   63.00   1.0000    1.3500
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -77.0000  150.0000 94

  5 omega    1.00   75.00   1.0000    1.3500
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000  -30.0000 74

  6 omega   22.00   88.00   1.0000    1.3500
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -123.0000  111.0000 66

  7 omega   38.00   91.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

  8 omega   38.00   91.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

  9 omega   38.00   91.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 10 omega  100.00  178.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 78

 11 omega   81.00  176.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 12 omega   57.00  150.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 93

 13 omega   39.00  109.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 14 omega   95.00  133.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -149.0000  -52.0000 38

 15 omega   73.00   98.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 25

 16 omega   39.00   89.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 50

 17 omega   41.00  126.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -180.0000 85

 18 omega   66.00  102.00   1.0000    1.3500
omega____ theta____ kappa____ phi______ frames
    -       36.6671   38.0000 -150.0000 36

 19 omega  149.00  176.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 27

 20 omega   79.00  104.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 25

 21 omega  110.00  135.00   1.0000    5.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.0219307000
_diffrn_orient_matrix_UB_12      0.0344726000
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_diffrn_orient_matrix_UB_21      0.0129612000
_diffrn_orient_matrix_UB_22      0.0686935000
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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  0.0438
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       8
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_diffrn_reflns_number            22081
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.575
_diffrn_reflns_theta_min         4.887
_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 colourless'
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_exptl_crystal_size_max          0.8
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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^)+(0.1079P)^2^+0.6301P] where P=(Fo^2^+2Fc^2^)/3'
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;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H006), C8(H009)
2.b Secondary CH2 refined with riding coordinates:
 C24(H00a,H00b)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H008), C10(H00C), C22(H00D), C19(H00F), C17(H00H), C13(H00J), C5(H00K),
 C15(H00L), C1(H00M), C14(H00N), C16(H00O), C4(H00P), C3(H00Q), C2(H00R)
;
_shelx_res_checksum              75853
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_olex2_date_sample_data_collection 2018-01-12
_olex2_submission_special_instructions 'No special instructions were received'