Discovery and bioinspired total syntheses of unprecedented sesquiterpenoid dimers unveiled bifurcating [4 + 2] cycloaddition and target differentiation of enantiomers.
He, Tao-Bin; Yan, Bing-Chao; Zhou, Yuan-Fei; Sang, Yue-Qian; Li, Xiao-Nian; Sun, Han-Dong; Wang, Chu; Xue, Xiao-Song; Puno, Pema-Tenzin; Chemical science 15 (2024) 1260–1270; doi:10.1039/d3sc05233h

data_1570418
_publ_section_title
;
 Discovery and bioinspired total syntheses of unprecedented
 sesquiterpenoid dimers unveiled bifurcating [4 + 2] cycloaddition and
 target differentiation of enantiomers.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              1260
_journal_page_last               1270
_journal_paper_doi               10.1039/d3sc05233h
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H38 O6, 0.5(C H4 O)'
_chemical_formula_sum            'C30.5 H40 O6.5'
_chemical_formula_weight         510.62
_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
;
2022-10-14 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.393(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6927(9)
_cell_length_b                   29.467(3)
_cell_length_c                   11.3135(12)
_cell_measurement_reflns_used    9471
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      72.57
_cell_measurement_theta_min      4.23
_cell_volume                     2679.4(5)
_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      130(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_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  0.0432
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            33070
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.733
_diffrn_reflns_theta_min         2.999
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             1100
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.5863
_exptl_transmission_factor_min   0.4933
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 4885 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(4)
_refine_ls_extinction_coef       0.0037(5)
_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   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     691
_refine_ls_number_reflns         10338
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0626P)^2^+1.1553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                10282
_reflns_number_total             10338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05233h2.cif
_cod_data_source_block           cu_20171024_KMZWS_1_0m_a
_cod_depositor_comments
;
Adding full bibliography for 1570418--1570425.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C61 H80 O13'
_cod_original_formula_weight         1021.25
_cod_original_formula_moiety         '2(C30 H38 O6), C H4 O'
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1570418
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.871
_shelx_estimated_absorpt_t_max   0.946
_shelx_res_checksum              40038