The Total Synthesis of (-)-Scabrolide A.
Hafeman, Nicholas J.; Loskot, Steven A.; Reimann, Christopher E.; Pritchett, Beau P.; Virgil, Scott C.; Stoltz, Brian M.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c02513

data_4134847
_publ_section_title
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 The Total Synthesis of (-)-Scabrolide A.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02513
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H34 O4 Si'
_chemical_formula_sum            'C27 H34 O4 Si'
_chemical_formula_weight         450.63
_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     dual
_audit_creation_date             2020-02-22
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003),
 SHELXL-2018/3, and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 90.920(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9085(14)
_cell_length_b                   10.3765(19)
_cell_length_c                   17.058(3)
_cell_measurement_reflns_used    9732
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.78
_cell_measurement_theta_min      2.30
_cell_volume                     1222.7(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker-AXS, 2016)'
_computing_data_collection
'BIS 2018.9.0.2/05-Oct-2018 & APEX3_2019.1-0 (Bruker-AXS, 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Kappa'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Triumph focusing graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            76181
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.803
_diffrn_reflns_theta_min         2.297
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'XRD C-TECH Long Fine Focus'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0605 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.9658.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 3000 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         8271
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0453P)^2^+0.2224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                7343
_reflns_number_total             8271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02513_si_003.cif
_cod_data_source_block           d20010
_cod_database_code               4134847
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.960
_refine_ls_abs_structure_hooft   0.03(2)
_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.a Ternary CH refined with riding coordinates:
 C12(H12), C16(H16), C18(H18), C22(H22), C24(H24), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C21(H21A,H21B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C20(H20A,H20B,H20C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              64231
_shelx_hkl_checksum              90472
_olex2_submission_special_instructions 'No special instructions were received'