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_7157636
_publ_section_title
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 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         'C17 H28 O4'
_chemical_formula_sum            'C17 H28 O4'
_chemical_formula_weight         296.39
_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
;
2020-06-26 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.6270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.2304(14)
_cell_length_b                   9.1246(8)
_cell_length_c                   22.238(2)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    90
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.38
_cell_volume                     3075.6(5)
_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
;
Platon (A.L.Spek, 2003)
Olex2 1.3-alpha (Dolomanov et al., 2009)
;
_computing_publication_material
;
Olex2 1.3-alpha (Dolomanov et al., 2009)
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0310
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32814
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.468
_diffrn_reflns_theta_min         1.343
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9303
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0920 before and 0.0451 after correction.
The Ratio of minimum to maximum transmission is 0.9303.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_recrystallization_method
'slow crystallization from a  hexane solution at room temperature'
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6332
_refine_ls_number_restraints     528
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0839P)^2^+1.5015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5308
_reflns_number_total             6332
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {bfd269a6-aa82-4fe0-8157-bb85ba00bbfc}
_cod_data_source_file            d0ob01430c2.cif
_cod_data_source_block           p21c_2
_cod_depositor_comments
'Adding full bibliography for 7157636--7157637.cif.'
_cod_database_code               7157636
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.972
_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 0.02 and sigma
for terminal atoms of 0.002 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.5 and sigma
for terminal atoms of 0.1
3.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C4S(H4S), C7S(H7S)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,
 H13B), C16(H16A,H16B), C2S(H2SA,H2SB), C5S(H5SA,H5SB), C6S(H6SA,H6SB),
 C9S(H9SA,H9SB), C10S(H10C,H10D), C13S(H13C,H13D), C16S(H16C,H16D)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C14S(H14S)
3.d X=CH2 refined with riding coordinates:
 C15(H15A,H15B), C15S(H15C,H15D)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C12S(H12D,H12E,H12F), C17S(H17D,
 H17E,H17F)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4A), O2S(H2S), O3S(H3S), O4S(H4SA)
;
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
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