Three-component modular synthesis of chiral 1,3-dioxoles <i>via</i> a Rh-catalyzed carbenic olefination cascade.
Huang, Shisheng; Luo, Jilong; Chen, Ping; Chen, Jiean; Wang, Zhaofeng; Chemical science 15 (2024) 18564–18571; doi:10.1039/d4sc06166g

data_1572874
_publ_section_title
;
 Three-component modular synthesis of chiral 1,3-dioxoles <i>via</i> a
 Rh-catalyzed carbenic olefination cascade.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              18564
_journal_page_last               18571
_journal_paper_doi               10.1039/d4sc06166g
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H20 O4'
_chemical_formula_weight         372.40
_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-2018/3
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.57076(8)
_cell_length_b                   7.79768(12)
_cell_length_c                   42.0452(6)
_cell_measurement_reflns_used    7349
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      76.1640
_cell_measurement_theta_min      2.1050
_cell_volume                     1826.40(5)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      105(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            9451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.348
_diffrn_reflns_theta_min         2.102
_exptl_absorpt_coefficient_mu    0.742
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1325 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_coef       0.0018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0384P)^2^+0.2399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0803
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                3456
_reflns_number_total             3628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06166g2.cif
_cod_data_source_block           wzf-20230712_auto
_cod_depositor_comments          'Adding full bibliography for 1572874.cif.'
_cod_database_code               1572874
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              9008
_shelx_hkl_checksum              88279