Asymmetric Total Synthesis of (-)-Spirochensilide A.
Liang, Xin-Ting; Chen, Jia-Hua; Yang, Zhen; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c02522

data_4134752
_publ_section_title
;
 Asymmetric Total Synthesis of (-)-Spirochensilide A.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02522
_journal_year                    2020
_chemical_formula_moiety         'C33 H59 Cl O3 Si2'
_chemical_formula_sum            'C33 H59 Cl O3 Si2'
_chemical_formula_weight         595.43
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-09
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.884(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9749(3)
_cell_length_b                   24.6837(8)
_cell_length_c                   13.5232(4)
_cell_measurement_reflns_used    3530
_cell_measurement_temperature    104.6
_cell_measurement_theta_max      29.2390
_cell_measurement_theta_min      3.0069
_cell_volume                     3644.15(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      104.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -9.00   88.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9711   77.0000  -30.0000 97

  2 omega   38.00   92.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9711   37.0000  -90.0000 54

  3 omega  -48.00   50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9711  -77.0000  150.0000 98

  4 omega   19.00   46.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9711  -37.0000 -180.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0134377000
_diffrn_orient_matrix_UB_12      -0.0035190000
_diffrn_orient_matrix_UB_13      -0.0497910000
_diffrn_orient_matrix_UB_21      -0.0014235000
_diffrn_orient_matrix_UB_22      -0.0285220000
_diffrn_orient_matrix_UB_23      0.0062435000
_diffrn_orient_matrix_UB_31      -0.0635422000
_diffrn_orient_matrix_UB_32      -0.0001174000
_diffrn_orient_matrix_UB_33      -0.0161954000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18351
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.013
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         7160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0363P)^2^+1.5996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5350
_reflns_number_total             7160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02522_si_004.cif
_cod_data_source_block           exp_4588
_cod_original_cell_volume        3644.16(18)
_cod_database_code               4134752
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.925
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Ternary CH refined with riding coordinates:
 C15(H15), C4(H4), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C9(H9A,H9B), C10(H10A,H10B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C33(H33A,H33B,H33C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C28(H28A,H28B,H28C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C17(H17A,
 H17B,H17C), C27(H27A,H27B,H27C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C),
 C26(H26A,H26B,H26C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C)
;
_shelx_res_checksum              28011
_shelx_hkl_checksum              39071
_olex2_submission_special_instructions 'No special instructions were received'