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_1565837
_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 H20 O4'
_chemical_formula_sum            'C25 H20 O4'
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_space_group_crystal_system      hexagonal
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_space_group_name_Hall           'P 61'
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_atom_sites_solution_hydrogens   mixed
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_atom_sites_solution_secondary   difmap
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_audit_update_record
;
2020-05-16 deposited with the CCDC.	2021-12-27 downloaded from the CCDC.
;
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_cell_angle_gamma                120
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_cell_length_b                   17.6742(3)
_cell_length_c                   11.6231(3)
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_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      80.25
_cell_measurement_theta_min      2.89
_cell_volume                     3144.36(11)
_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      170(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33839
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.679
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_diffrn_reflns_theta_min         2.887
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.7971
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
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_exptl_crystal_F_000             1212
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.234
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_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 1680 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_coef       0.0015(3)
_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   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4224
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.6174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.861
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                4032
_reflns_number_total             4224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06025b2.cif
_cod_data_source_block           ljw001
_cod_depositor_comments
'Adding full bibliography for 1565837--1565838.cif.'
_cod_original_cell_volume        3144.36(15)
_cod_database_code               1565837
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.860
_shelx_estimated_absorpt_t_max   0.924
_shelx_res_checksum              45294
_shelx_hkl_checksum              37926
_shelx_fab_checksum              47984