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_4134848
_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         'C19 H26 O6'
_chemical_formula_sum            'C19 H26 O6'
_chemical_formula_weight         350.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-22
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.221(3)
_cell_length_b                   12.581(3)
_cell_length_c                   13.333(4)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      35.79
_cell_measurement_theta_min      2.51
_cell_volume                     1714.5(8)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection
'BIS 2018.9.0.2/05-Oct-2018 & APEX3_2018.7-2 (Bruker-AXS, 2018)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0477
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            73152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.285
_diffrn_reflns_theta_min         2.226
_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    0.100
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0554 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.9208.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       lozenge
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 2628 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         7997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0555P)^2^+0.1628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                6804
_reflns_number_total             7997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02513_si_002.cif
_cod_data_source_block           d19153
_cod_original_cell_volume        1714.4(8)
_cod_database_code               4134848
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.970
_refine_ls_abs_structure_hooft   0.26(15)
_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:
 C1(H1A), C5(H5), C6(H6A), C7(H7), C12(H12), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B), C14(H14A,H14B), C16(H16A,H16B), C18(H18A,H18B)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O6(H6)
;
_shelx_res_checksum              23327
_shelx_hkl_checksum              8063
_olex2_submission_special_instructions 'No special instructions were received'