Asymmetric Total Synthesis of Lancifodilactone G Acetate.
Liu, Dong-Dong; Sun, Tian-Wen; Wang, Kuang-Yu; Lu, Yong; Zhang, Su-Lei; Li, Yuan-He; Jiang, Yan-Long; Chen, Jia-Hua; Yang, Zhen; Journal of the American Chemical Society 139 (2017) 5732–5735; doi:10.1021/jacs.7b02561

data_4125923
_publ_section_title
;
 Asymmetric Total Synthesis of Lancifodilactone G Acetate.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5732
_journal_page_last               5735
_journal_paper_doi               10.1021/jacs.7b02561
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C31 H38 O11'
_chemical_formula_sum            'C31 H38 O11'
_chemical_formula_weight         586.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                80.090(7)
_cell_angle_beta                 81.320(7)
_cell_angle_gamma                77.271(7)
_cell_formula_units_Z            4
_cell_length_a                   13.8165(11)
_cell_length_b                   16.1678(12)
_cell_length_c                   17.3578(17)
_cell_measurement_reflns_used    2578
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      21.8010
_cell_measurement_theta_min      3.0370
_cell_volume                     3699.8(6)
_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, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega  -61.00   38.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -57.0000 -120.0000 99

  2 omega  -20.00   53.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -99.0000  150.0000 73

  3 omega  -17.00   81.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454   57.0000   30.0000 98
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0488716000
_diffrn_orient_matrix_UB_12      0.0124706000
_diffrn_orient_matrix_UB_13      0.0192188000
_diffrn_orient_matrix_UB_21      -0.0027990000
_diffrn_orient_matrix_UB_22      -0.0437032000
_diffrn_orient_matrix_UB_23      0.0120200000
_diffrn_orient_matrix_UB_31      0.0203074000
_diffrn_orient_matrix_UB_32      0.0003378000
_diffrn_orient_matrix_UB_33      0.0350862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.2367
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_number            12761
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.026
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63870
_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    1.053
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
;
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     769
_refine_ls_number_reflns         12761
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.836
_refine_ls_R_factor_all          0.1790
_refine_ls_R_factor_gt           0.0882
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0676P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.2179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4935
_reflns_number_total             12761
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b02561_si_001.cif
_cod_data_source_block           exp_6828-sr
_cod_depositor_comments
'Adding full bibliography for 4125922--4125923.cif.'
_cod_database_code               4125923
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C1 N1 O1'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.992
_reflns_odcompleteness_completeness 99.23
_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. Uiso/Uaniso restraints and constraints
Uanis(C28) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.008
3.a Ternary CH refined with riding coordinates:
 C2(H2), C12(H12), C13(H13), C16(H16), C18(H18), C24(H24), C33(H33), C42(H42),
 C44(H44), C45(H45), C48(H48), C55(H55)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C15(H15A,H15B), C22(H22A,
 H22B), C23(H23A,H23B), C26(H26A,H26B), C34(H34A,H34B), C37(H37A,H37B),
 C41(H41A,H41B), C49(H49A,H49B), C50(H50A,H50B), C53(H53A,H53B), C54(H54A,H54B),
  C57(H57A,H57B)
3.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C31(H31A,H31B,H31C), C56(H56A,H56B,H56C), C58(H58A,H58B,H58C), C59(H59A,
 H59B,H59C), C60(H60A,H60B,H60C), C62(H62A,H62B,H62C)
3.d Idealised tetrahedral OH refined as rotating group:
 O11(H11), O22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'