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_1554799
_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         'C27 H40 O6'
_chemical_formula_sum            'C27 H40 O6'
_chemical_formula_weight         460.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 101.1380(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8327(3)
_cell_length_b                   16.9840(6)
_cell_length_c                   16.2007(5)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.50
_cell_measurement_theta_min      2.60
_cell_volume                     2654.54(15)
_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 0.962
_diffrn_measured_fraction_theta_max 0.938
_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  0.0456
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23335
_diffrn_reflns_point_group_measured_fraction_full 0.812
_diffrn_reflns_point_group_measured_fraction_max 0.789
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.247
_diffrn_reflns_theta_min         2.780
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          1.320
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.500
_exptl_transmission_factor_max   0.5853
_exptl_transmission_factor_min   0.4162
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 2764 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.16(9)
_refine_ls_extinction_coef       0.0027(6)
_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   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         7830
_refine_ls_number_restraints     305
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1229P)^2^+0.3834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1773
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.650
_reflns_Friedel_fraction_max     0.629
_reflns_number_gt                7524
_reflns_number_total             7830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00245f2.cif
_cod_data_source_block           cu_zyh_zn1216_0m
_cod_original_cell_volume        2654.53(15)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554799
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.483
_shelx_estimated_absorpt_t_max   0.739
_shelx_res_checksum              48411
_shelx_hkl_checksum              38146