Bioinspired Synthesis of Pentacyclic Onocerane Triterpenoids
Bartels, Florian; Hong, Young J.; Ueda, Daijiro; Weber, Manuela; Sato, Tsutomu; Tantillo, Dean J.; Christmann, Mathias; Chem. Sci.  (2017) –; doi:10.1039/C7SC03903D

data_1547684
_publ_section_title
;
 Bioinspired Synthesis of Pentacyclic Onocerane Triterpenoids
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC03903D
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H31.5 O1.12'
_chemical_formula_weight         265.93
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-22 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            8
_cell_length_a                   23.112(4)
_cell_length_b                   23.112
_cell_length_c                   7.05320(10)
_cell_measurement_reflns_used    7106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.16
_cell_measurement_theta_min      2.69
_cell_volume                     3262.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'X-STEP32, Microsoft Word'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            29710
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.419
_diffrn_reflns_theta_min         2.692
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_description       block
_exptl_crystal_F_000             1188
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc / Hexan'
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_exptl_transmission_factor_max   0.9705
_exptl_transmission_factor_min   0.8630
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 2388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(8)
_refine_ls_extinction_coef       0.0079(13)
_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   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         8894
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0958
_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^)+(0.0499P)^2^+10.2541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2161
_refine_ls_wR_factor_ref         0.2294
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                6809
_reflns_number_total             8894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03903d2.cif
_cod_data_source_block           fb1314aa_a
_cod_original_cell_volume        3262.78(12)
_cod_original_formula_sum        'C18 H31.50 O1.12'
_cod_database_code               1547684
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              44700