Concise asymmetric synthesis of (-)-Bao Gong Teng A <i>via</i> Evans chiral auxiliary-based 1,3-dipolar cycloaddition.
Zhao, Yi-Wen; Wang, Jun-Fei; Xu, Jianrong; Chen, Hongzhuan; Tan, Yun-Xuan; Tian, Ping; Organic & biomolecular chemistry 23 (2025) 2370–2374; doi:10.1039/d5ob00014a

data_7160358
_publ_section_title
;
 Concise asymmetric synthesis of (-)-Bao Gong Teng A <i>via</i> Evans
 chiral auxiliary-based 1,3-dipolar cycloaddition.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2370
_journal_page_last               2374
_journal_paper_doi               10.1039/d5ob00014a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H25 Cl N2 O4'
_chemical_formula_weight         512.97
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-11-15 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.156(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6891(4)
_cell_length_b                   8.3323(3)
_cell_length_c                   13.3055(5)
_cell_measurement_reflns_used    8529
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      63.4421
_cell_measurement_theta_min      3.5619
_cell_volume                     1311.97(8)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'd8 venture'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23724
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        65.253
_diffrn_reflns_theta_max         65.253
_diffrn_reflns_theta_min         3.562
_exptl_absorpt_coefficient_mu    1.603
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1094 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.104(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4440
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0770P)^2^+0.1578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1560
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3233
_reflns_number_total             4440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00014a2.cif
_cod_data_source_block           cu_20231107_ZYW_1X_28_3_0m
_cod_depositor_comments
'Adding full bibliography for 7160357--7160359.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7160358
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.581
_shelx_estimated_absorpt_t_max   0.772
_shelx_res_checksum              42717