Concise synthesis of chiral γ-butenolides <i>via</i> an allylation/lactonization cascade reaction.
Tan, Zheng; Yihuo, Aying; Wu, Zhao; Wang, Fei; Dong, Shunxi; Feng, Xiaoming; Chemical communications (Cambridge, England) 60 (2024) 7926–7929; doi:10.1039/d4cc02781g

data_7133268
_publ_section_title
;
 Concise synthesis of chiral &#x3b3;-butenolides <i>via</i> an
 allylation/lactonization cascade reaction.
;
_journal_issue                   61
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7926
_journal_page_last               7929
_journal_paper_doi               10.1039/d4cc02781g
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H18 O4'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_weight         322.34
_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     dual
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-02-08 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.34150(10)
_cell_length_b                   8.4205(2)
_cell_length_c                   30.8465(7)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      2.87
_cell_volume                     1647.16(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            12771
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.267
_diffrn_reflns_theta_min         2.865
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.9096
_exptl_absorpt_correction_T_min  0.7301
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       rod
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: IPA'
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.441
_exptl_crystal_size_min          0.228
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 1219 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_coef       0.0157(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+0.2851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0664
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2993
_reflns_number_total             3013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02781g2.cif
_cod_data_source_block           tqf022
_cod_depositor_comments          'Adding full bibliography for 7133268.cif.'
_cod_database_code               7133268
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.697
_shelx_estimated_absorpt_t_max   0.850
_shelx_res_checksum              17901
_shelx_hkl_checksum              85128