Total Synthesis of Isomalabaricane Triterpenoids.
Boyko, Yaroslav D.; Huck, Christopher J.; Sarlah, David; Journal of the American Chemical Society 141 (2019) 14131–14135; doi:10.1021/jacs.9b08487

data_4128796
_publ_section_title
;
 Total Synthesis of Isomalabaricane Triterpenoids.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14131
_journal_page_last               14135
_journal_paper_doi               10.1021/jacs.9b08487
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C19 H28 O3'
_chemical_formula_sum            'C19 H28 O3'
_chemical_formula_weight         304.41
_chemical_name_systematic
(3aS*,5aR*,9aR*)-3-acetyl-2-hydroxy-3a,6,6,9a-tetramethyl-1,3a,4,5,5a,6,8,9,9a,9b-decahydro-7H-cyclopenta[a]naphthalen-7-one
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-06 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                72.958(2)
_cell_angle_beta                 83.610(2)
_cell_angle_gamma                77.293(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6780(3)
_cell_length_b                   9.4722(4)
_cell_length_c                   13.5770(6)
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.370
_cell_measurement_theta_min      2.294
_cell_volume                     799.99(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_type            'photon counter area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31524
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_min         2.394
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1176 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.9532. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method
'Crystallized by slow evaporation of dichloromethane from a solution in dichloromethane + isopropanol'
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.068(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0474P)^2^+0.4595P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3484
_reflns_number_total             3984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08487_si_003.cif
_cod_data_source_block           mo_dd16q_0m
_cod_database_code               4128796
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C5(H5), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B)
3.c Disordered Me refined as rotating group:
 C15(H15A,H15B,H15C,H15D,H15E,H15F)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_shelx_res_checksum              48327
_shelx_hkl_checksum              96465
_olex2_date_sample_data_collection 2018-09-13
_olex2_date_sample_submission    2018-09-12
_olex2_exptl_crystal_mounting_method
'Mounted on a cryoloop (Hampton research) using Paratone oil (Exxon) with (-1 0 -1) face rougly perpendicular to the spindle axis '
_olex2_submission_original_sample_id YB-VIII-264
_olex2_submission_special_instructions 'No special instructions were received'