Asymmetric synthesis of the fully functionalized six-membered A-ring of siphonol A.
Sun, Ying; Fu, Shaomin; Liu, Bo; Organic & biomolecular chemistry 22 (2024) 2958–2962; doi:10.1039/d4ob00104d

data_7159844
_publ_section_title
;
 Asymmetric synthesis of the fully functionalized six-membered A-ring of
 siphonol A.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2958
_journal_page_last               2962
_journal_paper_doi               10.1039/d4ob00104d
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H42 O6 Si'
_chemical_formula_sum            'C23 H42 O6 Si'
_chemical_formula_weight         442.65
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-10-05 deposited with the CCDC.	2024-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7582(2)
_cell_length_b                   12.2091(2)
_cell_length_c                   18.8089(4)
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      79.43
_cell_measurement_theta_min      4.32
_cell_volume                     2470.51(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16699
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.420
_diffrn_reflns_theta_min         4.317
_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5042
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.797
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
; 
 Flack x determined using 2088 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.058(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         5182
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0610P)^2^+0.5596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                5028
_reflns_number_total             5182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00104d2.cif
_cod_data_source_block           lib025
_cod_depositor_comments          'Adding full bibliography for 7159844.cif.'
_cod_database_code               7159844
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.470
_shelx_estimated_absorpt_t_max   0.851
_shelx_res_checksum              12814