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_4129585
_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 unk
_chemical_formula_moiety         'C11 H11 I O2'
_chemical_formula_sum            'C11 H11 I O2'
_chemical_formula_weight         302.10
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.269(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6632(10)
_cell_length_b                   7.4512(8)
_cell_length_c                   16.987(2)
_cell_measurement_reflns_used    1854
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.1250
_cell_measurement_theta_min      3.3970
_cell_volume                     1096.3(2)
_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      100.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -12.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   38.0000  120.0000 95

  2 omega  -82.00    5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.8735  -77.0000 -120.0000 87

  3 omega  -19.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.8735  -99.0000 -180.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0401830000
_diffrn_orient_matrix_UB_12      0.0455105000
_diffrn_orient_matrix_UB_13      0.0300133000
_diffrn_orient_matrix_UB_21      -0.0015895000
_diffrn_orient_matrix_UB_22      -0.0800945000
_diffrn_orient_matrix_UB_23      0.0224207000
_diffrn_orient_matrix_UB_31      0.0712746000
_diffrn_orient_matrix_UB_32      0.0238906000
_diffrn_orient_matrix_UB_33      0.0185450000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.1156
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5319
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.985
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19886
_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    1.830
_exptl_crystal_description
;
;
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.518
_refine_diff_density_min         -2.381
_refine_diff_density_rms         0.229
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3604
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0718
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0838P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1702
_reflns_Friedel_coverage         0.553
_reflns_Friedel_fraction_full    0.671
_reflns_Friedel_fraction_max     0.648
_reflns_number_gt                3094
_reflns_number_total             3604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b08551_si_002.cif
_cod_data_source_block           exp_5371
_cod_original_cell_volume        1096.2(2)
_cod_database_code               4129585
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         C11O2I1
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.761
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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
2. Restrained distances
 C1-C9
 1.54 with sigma of 0.01
 C20-C19
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.008
Uanis(C7) \\sim Ueq: with sigma of 0.008 and sigma for terminal atoms of 0.2
Uanis(C1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.2
Uanis(C4) \\sim Ueq: with sigma of 0.008 and sigma for terminal atoms of 0.2
4.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9), C12(H12), C20(H20)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C19(H19A,H19B)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17)
4.d Tetrahedral OH refined with riding coordinates:
 O2(H2), O4(H4A)
4.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'