Total synthesis of highly oxygenated phomopsol B <i>via</i> acid-induced etherification to construct a bridged structure.
Kawamoto, Yuichiro; Nishitani, Ayaka; Yoshimura, Yukari; Kobayashi, Toyoharu; Ito, Hisanaka; Chemical communications (Cambridge, England) 60 (2023) 95–97; doi:10.1039/d3cc05130g

data_7132369
_publ_section_title
;
 Total synthesis of highly oxygenated phomopsol B <i>via</i> acid-induced
 etherification to construct a bridged structure.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              95
_journal_page_last               97
_journal_paper_doi               10.1039/d3cc05130g
_journal_volume                  60
_journal_year                    2023
_chemical_formula_moiety         'C17 H26 O5 Si'
_chemical_formula_sum            'C17 H26 O5 Si'
_chemical_formula_weight         338.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-10-02 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                98.4750(10)
_cell_angle_beta                 107.9440(10)
_cell_angle_gamma                106.4410(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9252(8)
_cell_length_b                   9.8381(9)
_cell_length_c                   12.6943(12)
_cell_measurement_reflns_used    6161
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.99
_cell_measurement_theta_min      2.23
_cell_volume                     872.76(15)
_computing_cell_refinement       'SAINT V8.40B (2016)'
_computing_data_reduction        'SAINT V8.40B (2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      90
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_detector_type            'Bruker SMART APEX II CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    '0.5 mm  '
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10735
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.178
_diffrn_reflns_theta_min         1.745
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9374
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0712 before and 0.0345 after correction.
The Ratio of minimum to maximum transmission is 0.9425.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_recrystallization_method
'Single crystals  were grown from vapour diffusion of pentane in chloroform solvent at room temperature'
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.221
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     191
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0514P)^2^+0.4171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3963
_reflns_number_total             4301
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05130g2.cif
_cod_data_source_block           na-1-66-2
_cod_depositor_comments          'Adding full bibliography for 7132369.cif.'
_cod_original_cell_volume        872.76(14)
_cod_database_code               7132369
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.956
_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. Rigid body (RIGU) restrains
 C3, C7, C15, C2, O3, C1, C17, C5, C9, C4, C14, O5, C16, Si1, C6, C10, C8, C11,
  O1, C12, O4, C13, O2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3A)
;
_shelx_res_checksum              86005
_shelx_hkl_checksum              52292
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MiTeGEN MicroMounts in  perfluoropolyether oil'
_olex2_submission_special_instructions 'No special instructions were received'