Highly stereocontrolled total synthesis of secodolastane diterpenoid isolinearol.
Kobayashi, Toyoharu; Tomita, Yui; Kawamoto, Yuichiro; Ito, Hisanaka; Organic & biomolecular chemistry 18 (2020) 7316–7320; doi:10.1039/d0ob01430c

data_7157637
_publ_section_title
;
 Highly stereocontrolled total synthesis of secodolastane diterpenoid
 isolinearol.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7316
_journal_page_last               7320
_journal_paper_doi               10.1039/d0ob01430c
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H32 O4'
_chemical_formula_sum            'C20 H32 O4'
_chemical_formula_weight         336.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-10
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-05-14 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.146(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.559(2)
_cell_length_b                   8.9149(17)
_cell_length_c                   19.341(4)
_cell_measurement_reflns_used    5015
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.52
_cell_volume                     1819.3(6)
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX II Ultra'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16603
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.930
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1016 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.9601.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method
'slow crystallization from a ethyl acetate solution at room temperature'
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     300
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0437P)^2^+0.8708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2730
_reflns_number_total             3228
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {97f93579-9cbe-4926-8be2-e96004bc8ee7}
_cod_data_source_file            d0ob01430c2.cif
_cod_data_source_block           p21c_a
_cod_depositor_comments
'Adding full bibliography for 7157636--7157637.cif.'
_cod_database_code               7157637
_publcif_funding_html
;
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.981
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.002 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.05 and sigma
for terminal atoms of 0.1
3.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C2(H2A,H2B),
 C5(H5A,H5B), C6(H6A,H6B)
3.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2)
;
_olex2_exptl_crystal_mounting_method
'The  crystals were picked, soaked in perfluoropolyether oil and mounted on MiTeGen MicroMounts.'
_olex2_submission_special_instructions 'No special instructions were received'