Rearranged limonoids with unique 6/5/6/5 tetracarbocyclic skeletons from Toona ciliata and biomimetic structure divergence
Luo, Jun; Huang, Wan-Sha; Hu, Sheng-Mou; Zhang, Pan-Pan; Zhou, Xu-Wei; Wang, Xiao-Bing; Yang, Ming-Hua; Luo, Jian-Guang; Wang, Chen; Liu, Chang; Yao, He-Quan; Zhang, Can; Sun, Hong-Bin; Chen, Yi-Jun; Kong, Ling-Yi; Organic Chemistry Frontiers 4 (2017) 2417–; doi:10.1039/C7QO00678K

data_1553871
_publ_section_title
;
 Rearranged limonoids with unique 6/5/6/5 tetracarbocyclic skeletons from
 Toona ciliata and biomimetic structure divergence
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2417
_journal_paper_doi               10.1039/C7QO00678K
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C31 H38 O9'
_chemical_formula_weight         554.61
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-05-19 deposited with the CCDC.
2017-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.68150(10)
_cell_length_b                   17.2043(2)
_cell_length_c                   23.1115(2)
_cell_measurement_reflns_used    21524
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.2150
_cell_measurement_theta_min      3.9330
_cell_volume                     5837.62(9)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            42142
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.336
_diffrn_reflns_theta_min         3.567
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 4197 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     735
_refine_ls_number_reflns         11193
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0635
_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^)+(0.1220P)^2^+1.3538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1821
_refine_ls_wR_factor_ref         0.1891
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                10110
_reflns_number_total             11193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00678k2.cif
_cod_data_source_block           shelxl_CCDC1
_cod_database_code               1553871
_shelx_estimated_absorpt_t_min   0.863
_shelx_estimated_absorpt_t_max   0.901
_shelxl_version_number           2013-4
_shelx_res_checksum              21310
_shelx_hkl_checksum              52966