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_1547687
_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            'C30 H50 O3'
_chemical_formula_weight         458.70
_chemical_name_common            Cupacinoxepin
_space_group_crystal_system      tetragonal
_space_group_IT_number           77
_space_group_name_Hall           'P 4c'
_space_group_name_H-M_alt        'P 42'
_symmetry_space_group_name_Hall  'P 4c'
_symmetry_space_group_name_H-M   'P 42'
_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                90
_cell_formula_units_Z            4
_cell_length_a                   18.4576(2)
_cell_length_b                   18.4576
_cell_length_c                   7.45850(10)
_cell_measurement_reflns_used    5731
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.64
_cell_measurement_theta_min      2.39
_cell_volume                     2540.98(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  '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 0.999
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1428
_diffrn_reflns_av_unetI/netI     0.1067
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            24885
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.757
_diffrn_reflns_theta_max         66.757
_diffrn_reflns_theta_min         3.386
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Aceton/ Hexan'
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_transmission_factor_max   0.7923
_exptl_transmission_factor_min   0.7160
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1034 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0022(3)
_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   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4490
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0571
_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^)+(0.0396P)^2^+0.5688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3149
_reflns_number_total             4490
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03903d2.cif
_cod_data_source_block           FB1412Ba
_cod_database_code               1547687
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.814
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              62922