Asymmetric synthesis of isochromanone derivatives via trapping carboxylic oxonium ylides and aldol cascade
Lang, Jiawen; Wang, Siyuan; He, Changli; Liu, Xiaohua; Feng, Xiaoming; Chemical Science 13 (2022) 1163–1168; doi:10.1039/D1SC06025B

data_1565838
_publ_section_title
;
 Asymmetric synthesis of isochromanone derivatives via trapping carboxylic
 oxonium ylides and aldol cascade
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1163
_journal_page_last               1168
_journal_paper_doi               10.1039/D1SC06025B
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H22 O4'
_chemical_formula_sum            'C25 H22 O4'
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_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-25 deposited with the CCDC.	2021-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.52630(10)
_cell_length_b                   13.9032(3)
_cell_length_c                   21.5712(4)
_cell_measurement_reflns_used    8338
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      4.10
_cell_volume                     1957.29(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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10060
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.254
_diffrn_reflns_theta_min         4.099
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  0.9397
_exptl_absorpt_correction_T_min  0.7942
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, iPrOH, PE'
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
; 
 Flack x determined using 1356 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3454
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0380P)^2^+0.1697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0752
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3307
_reflns_number_total             3454
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06025b2.cif
_cod_data_source_block           ljw005
_cod_depositor_comments
'Adding full bibliography for 1565837--1565838.cif.'
_cod_database_code               1565838
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.801
_shelx_estimated_absorpt_t_max   0.889
_shelx_res_checksum              99544
_shelx_hkl_checksum              27779