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_4125922
_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         'C42 H62 O9 Si2'
_chemical_formula_sum            'C42 H62 O9 Si2'
_chemical_formula_weight         767.09
_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             2016-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                91.379(3)
_cell_angle_beta                 98.913(3)
_cell_angle_gamma                90.225(3)
_cell_formula_units_Z            4
_cell_length_a                   14.5065(6)
_cell_length_b                   15.7580(7)
_cell_length_c                   19.4000(7)
_cell_measurement_reflns_used    9158
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.6610
_cell_measurement_theta_min      3.4580
_cell_volume                     4379.8(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      180.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27287
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.074
_exptl_absorpt_coefficient_mu    0.131
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.113
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1032
_refine_ls_number_reflns         16924
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0892
_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^)+(0.1383P)^2^+7.9345P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2589
_refine_ls_wR_factor_ref         0.2753
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12306
_reflns_number_total             16924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b02561_si_002.cif
_cod_data_source_block           exp_1685
_cod_depositor_comments
'Adding full bibliography for 4125922--4125923.cif.'
_cod_original_cell_volume        4379.7(3)
_cod_database_code               4125922
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C84-C79 \\sim C84-C83 \\sim C83-C82 \\sim C82-C81 \\sim C81-C80 \\sim C80-C79
 with sigma of 0.02
 C84A-C79A \\sim C84A-C83A \\sim C83A-C82A \\sim C82A-C81A \\sim C81A-C80A
\\sim C80A-C79A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C84 \\sim C79 \\sim C80 \\sim C81 \\sim C82 \\sim C83: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
C81A \\sim C80A \\sim C79A \\sim C84A \\sim C83A \\sim C82A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(H78C)=Sof(H78D)=Sof(C79A)=Sof(C80A)=Sof(H80A)=Sof(C84A)=Sof(H84A)=
 Sof(C83A)=Sof(H83A)=Sof(C81A)=Sof(H81A)=Sof(C82A)=Sof(H82A)=1-FVAR(1)
 Sof(H78A)=Sof(H78B)=Sof(C79)=Sof(C80)=Sof(H80)=Sof(C81)=Sof(H81)=Sof(C83)=
 Sof(H83)=Sof(C82)=Sof(H82)=Sof(C84)=Sof(H84)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C17(H17), C20(H20), C55(H55), C58(H58), C59(H59), C62(H62)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C18(H18A,H18B), C19(H19A,H19B),
 C23(H23A,H23B), C30(H30A,H30B), C32(H32A,H32B), C34(H34A,H34B), C36(H36A,H36B),
  C45(H45A,H45B), C47(H47A,H47B), C48(H48A,H48B), C60(H60A,H60B), C61(H61A,
 H61B), C65(H65A,H65B), C72(H72A,H72B), C74(H74A,H74B), C76(H76A,H76B),
 C78(H78A,H78B), C78(H78C,H78D)
5.c Aromatic/amide H refined with riding coordinates:
 C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C80(H80), C81(H81),
 C83(H83), C82(H82), C84(H84), C80A(H80A), C84A(H84A), C83A(H83A), C81A(H81A),
 C82A(H82A)
5.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,
 H29B,H29C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C),
 C50(H50A,H50B,H50C), C53(H53A,H53B,H53C), C64(H64A,H64B,H64C), C66(H66A,H66B,
 H66C), C67(H67A,H67B,H67C), C69(H69A,H69B,H69C), C70(H70A,H70B,H70C), C71(H71A,
 H71B,H71C), C73(H73A,H73B,H73C), C75(H75A,H75B,H75C), C77(H77A,H77B,H77C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'