Oxidative generation of isobenzofurans from phthalans: application to the formal synthesis of (±)-morphine.
Kage, Mirai; Yamakoshi, Hiroyuki; Tabata, Manami; Ohashi, Eisaku; Noguchi, Kimihiro; Watanabe, Takeshi; Uchida, Manato; Takada, Minetatsu; Ikeuchi, Kazutada; Nakamura, Seiichi; Chemical science 15 (2024) 19070–19076; doi:10.1039/d4sc05890a

data_1572906
_publ_section_title
;
 Oxidative generation of isobenzofurans from phthalans: application to the
 formal synthesis of (&#xb1;)-morphine.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              19070
_journal_page_last               19076
_journal_paper_doi               10.1039/d4sc05890a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C21 H29 N O5'
_chemical_formula_sum            'C21 H29 N O5'
_chemical_formula_weight         375.45
_space_group_crystal_system      triclinic
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-01-20 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                89.490(9)
_cell_angle_beta                 98.254(7)
_cell_angle_gamma                89.986(6)
_cell_formula_units_Z            2
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_cell_measurement_temperature    103(2)
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_cell_measurement_theta_min      2.6220
_cell_volume                     901.57(15)
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_computing_data_collection       CrystalClear
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  'Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)'
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_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103(2)
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_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.1089
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_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_k_max       13
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_diffrn_reflns_limit_l_max       13
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_diffrn_reflns_number            14919
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
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_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.849
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.997
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       platelet
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.525
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.322
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.1083
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2898
_refine_ls_wR_factor_ref         0.3177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2740
_reflns_number_total             3335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05890a2.cif
_cod_data_source_block           samp2
_cod_depositor_comments          'Adding full bibliography for 1572906.cif.'
_cod_database_code               1572906
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              82883
_shelx_hkl_checksum              98320