Enantioselective Total Synthesis of (-)-Incarviatone A.
Hong, Benke; Li, Chao; Wang, Zhen; Chen, Jie; Li, Houhua; Lei, Xiaoguang; Journal of the American Chemical Society 137 (2015) 11946–11949; doi:10.1021/jacs.5b08551

data_4129584
_publ_section_title
;
 Enantioselective Total Synthesis of (-)-Incarviatone A.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11946
_journal_page_last               11949
_journal_paper_doi               10.1021/jacs.5b08551
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H22 O5, H2 O'
_chemical_formula_sum            'C20 H24 O6'
_chemical_formula_weight         360.39
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.761(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4116(2)
_cell_length_b                   8.4114(3)
_cell_length_c                   14.1853(4)
_cell_measurement_reflns_used    2116
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      73.7220
_cell_measurement_theta_min      8.0130
_cell_volume                     874.02(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega -114.00  -87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -57.0000   90.0000 27

  2 omega -119.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -77.0000 -150.0000 109

  3 omega  -15.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306   38.0000  -30.0000 50

  4 omega  -36.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -57.0000   90.0000 25

  5 omega   29.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000 -150.0000 49

  6 omega   29.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000  120.0000 61

  7 omega   45.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000 -120.0000 61

  8 omega   29.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000    0.0000 56

  9 omega   45.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -61.0000  -90.0000 93

 10 omega   47.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000 -180.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0467824000
_diffrn_orient_matrix_UB_12      -0.0811780000
_diffrn_orient_matrix_UB_13      -0.0907656000
_diffrn_orient_matrix_UB_21      -0.1988434000
_diffrn_orient_matrix_UB_22      0.0223967000
_diffrn_orient_matrix_UB_23      -0.0486963000
_diffrn_orient_matrix_UB_31      0.0503610000
_diffrn_orient_matrix_UB_32      0.1625048000
_diffrn_orient_matrix_UB_33      -0.0383383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2724
_diffrn_reflns_point_group_measured_fraction_full 0.644
_diffrn_reflns_point_group_measured_fraction_max 0.664
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.576
_diffrn_reflns_theta_min         3.152
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description
;
;
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.1675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.244
_reflns_Friedel_fraction_full    0.272
_reflns_Friedel_fraction_max     0.281
_reflns_number_gt                1991
_reflns_number_total             2042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b08551_si_004.cif
_cod_data_source_block           exp_4999
_cod_database_code               4129584
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C20 O5 H22'
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.907
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C8(H8A,H8B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13)
2.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'