Asymmetric Total Synthesis of Propindilactone G.
You, Lin; Liang, Xin-Ting; Xu, Ling-Min; Wang, Yue-Fan; Zhang, Jia-Jun; Su, Qi; Li, Yuan-He; Zhang, Bo; Yang, Shou-Liang; Chen, Jia-Hua; Yang, Zhen; Journal of the American Chemical Society 137 (2015) 10120–10123; doi:10.1021/jacs.5b06480

data_4124259
_publ_section_title
;
 Asymmetric Total Synthesis of Propindilactone G.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10120
_journal_page_last               10123
_journal_paper_doi               10.1021/jacs.5b06480
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         '2(C22 H32 O5 Si), C4 H8 O2'
_chemical_formula_sum            'C48 H72 O12 Si2'
_chemical_formula_weight         897.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-06
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.539(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3335(6)
_cell_length_b                   38.200(3)
_cell_length_c                   19.9859(12)
_cell_measurement_reflns_used    6353
_cell_measurement_temperature    180.01(11)
_cell_measurement_theta_max      29.3090
_cell_measurement_theta_min      3.7670
_cell_volume                     4830.6(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.01(11)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9959
_diffrn_measured_fraction_theta_max 0.8359
_diffrn_measurement_details
;
  1 omega  -36.00   56.00   1.0000    7.9100
omega____ theta____ kappa____ phi______ frames
    -      -11.1704   57.0000 -180.0000 92

  2 omega  -83.00   14.00   1.0000    7.9100
omega____ theta____ kappa____ phi______ frames
    -      -11.1704  -57.0000   30.0000 97
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0127252000
_diffrn_orient_matrix_UB_12      -0.0072778000
_diffrn_orient_matrix_UB_13      -0.0324539000
_diffrn_orient_matrix_UB_21      0.0033468000
_diffrn_orient_matrix_UB_22      0.0170620000
_diffrn_orient_matrix_UB_23      -0.0141737000
_diffrn_orient_matrix_UB_31      0.1114382000
_diffrn_orient_matrix_UB_32      -0.0013473000
_diffrn_orient_matrix_UB_33      -0.0017236000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20958
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.24
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         9484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+3.8018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                7236
_reflns_number_total             9484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b06480_si_001.cif
_cod_data_source_block           exp_1919
_cod_depositor_comments
'Adding full bibliography for 4124259--4124260.cif.'
_cod_database_code               4124259
_chemical_oxdiff_formula         'C19 H22 O5'
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H14 of C14, {H28A,H28B} of C28, {H15A,H15B} of C15, H36 of C36, H16 of C16,
  {H9A,H9B} of C9, {H3A,H3B} of C3, H38 of C38, {H6A,H6B} of C6, {H5A,H5B} of
  C5, {H27A,H27B} of C27, {H47A,H47B} of C47, {H37A,H37B} of C37, {H25A,H25B}
  of C25, {H31A,H31B} of C31
 At 1.5 times of:
  {H20A,H20B,H20C} of C20, {H18A,H18B,H18C} of C18, {H19A,H19B,H19C} of C19,
  {H8A,H8B,H8C} of C8, {H42A,H42B,H42C} of C42, {H43A,H43B,H43C} of C43, {H48A,
  H48B,H48C} of C48, {H41A,H41B,H41C} of C41, {H44A,H44B,H44C} of C44, {H45A,
  H45B,H45C} of C45, {H30A,H30B,H30C} of C30, {H40A,H40B,H40C} of C40, H3 of O3,
   H4 of O4, {H22A,H22B,H22C} of C22, {H21A,H21B,H21C} of C21, H9 of O9, H8 of
  O8
2.a Ternary CH refined with riding coordinates:
 C16(H16), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C15(H15A,H15B), C25(H25A,
 H25B), C27(H27A,H27B), C28(H28A,H28B), C31(H31A,H31B), C37(H37A,H37B),
 C47(H47A,H47B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C36(H36)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C30(H30A,H30B,H30C), C40(H40A,
 H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C),
 C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C48(H48A,H48B,H48C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O8(H8), O9(H9)
;