A divergent strategy to synthesize gabosines featuring a switchable two-way aldol cyclization.
Yang, Xing; Yuan, Po; Shui, Feng; Zhou, Yuqin; Chen, Xiaochuan; Organic & biomolecular chemistry 17 (2019) 4061–4072; doi:10.1039/c9ob00469f

data_7156740
_publ_section_title
;
 A divergent strategy to synthesize gabosines featuring a switchable
 two-way aldol cyclization.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4061
_journal_page_last               4072
_journal_paper_doi               10.1039/c9ob00469f
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 O7'
_chemical_formula_sum            'C20 H24 O7'
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_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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2017-03-29 deposited with the CCDC.    2019-03-22 downloaded from the CCDC.
;
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_cell_measurement_theta_min      5.0770
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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)
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_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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  120.0000 84

  2 omega  -32.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000 -180.0000 95

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

  4 omega  -14.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -86.0000   22.0000 82

  5 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000    0.0000 66

  7 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  -60.0000 84

  8 omega   10.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -109.0000  130.0000 71

  9 omega   91.00  176.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
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 10 omega   70.00  178.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
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 11 omega   40.00   98.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 12 omega   38.00   91.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 13 omega   40.00   65.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 25
;
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_diffrn_orient_matrix_UB_11      -0.0315970000
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_diffrn_orient_matrix_UB_21      0.0828500000
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_diffrn_orient_matrix_UB_32      -0.0798588000
_diffrn_orient_matrix_UB_33      -0.0071727000
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
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_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_max       9
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_diffrn_reflns_theta_full        67.023
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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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.
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_exptl_crystal_colour            'clear light colourless'
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_exptl_crystal_F_000             1600
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;
 Flack x determined using 1110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(12)
_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^)+(0.0703P)^2^+10.9478P] where P=(Fo^2^+2Fc^2^)/3'
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_cod_depositor_comments          'Adding full bibliography for 7156740.cif.'
_cod_original_cell_volume        3711.37(16)
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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.a Ternary CH refined with riding coordinates:
 C008(H008), C00D(H00D), C00O(H00O)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00G,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00J(H00J), C00L(H00L)
2.d Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00E), C00M(H00I,H00K,H00M), C00P(H00N,H00P,H00Q), C00Q(H00R,
 H00S,H00T), C00R(H00U,H00V,H00W)
;
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_olex2_date_sample_data_collection 2016-04-05
_olex2_submission_special_instructions 'No special instructions were received'