The absolute configurations of hyperilongenols A–C: rare 12,13-seco-spirocyclic polycyclic polyprenylated acylphloroglucinols with enolizable β,β′-tricarbonyl systems from Hypericum longistylum Oliv.
Zhang, Na; Shi, Zhengyi; Guo, Yi; Xie, Shuangshuang; Qiao, Yuben; Li, Xiao-Nian; Xue, Yongbo; Luo, Zengwei; Zhu, Hucheng; Chen, Chunmei; Hu, Linzhen; Zhang, Yonghui; Organic Chemistry Frontiers 6 (2019) 1491–; doi:10.1039/C9QO00245F

data_1554800
_publ_section_title
;
 The absolute configurations of hyperilongenols A--C: rare
 12,13-seco-spirocyclic polycyclic polyprenylated acylphloroglucinols with
 enolizable \b,\b&#x2032;-tricarbonyl systems from Hypericum longistylum
 Oliv.
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1491
_journal_paper_doi               10.1039/C9QO00245F
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H44 O6'
_chemical_formula_sum            'C29 H44 O6'
_chemical_formula_weight         488.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-10-16 deposited with the CCDC.	2019-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0011(3)
_cell_length_b                   13.3921(3)
_cell_length_c                   17.7454(4)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.88
_cell_measurement_theta_min      8.35
_cell_volume                     2852.04(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16335
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.223
_diffrn_reflns_theta_min         7.979
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_description       prism
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.860
_exptl_crystal_size_mid          0.550
_exptl_crystal_size_min          0.460
_exptl_transmission_factor_max   0.7532
_exptl_transmission_factor_min   0.5989
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0456P)^2^+0.5417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                4938
_reflns_number_total             4950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00245f2.cif
_cod_data_source_block           cu_zyh_zn1379_0m
_cod_database_code               1554800
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.615
_shelx_estimated_absorpt_t_max   0.762
_shelx_res_checksum              94384
_shelx_hkl_checksum              60361