Asymmetric dearomatization of benzyl 1-naphthyl ethers <i>via</i> [1,3] O-to-C rearrangement.
Zeng, Hongkun; Wen, Gang; Lin, Lili; Feng, Xiaoming; Chemical communications (Cambridge, England) 60 (2024) 7507–7510; doi:10.1039/d4cc02620a

data_7133234
_publ_section_title
;
 Asymmetric dearomatization of benzyl 1-naphthyl ethers <i>via</i> [1,3]
 O-to-C rearrangement.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7507
_journal_page_last               7510
_journal_paper_doi               10.1039/d4cc02620a
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 O4'
_chemical_formula_sum            'C21 H20 O4'
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_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_audit_update_record
;
2023-07-22 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;
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_cell_angle_gamma                90
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_cell_length_b                   12.3659(2)
_cell_length_c                   16.7686(3)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      2.63
_cell_volume                     1771.32(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'
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_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
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_diffrn_reflns_limit_l_min       -17
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
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_diffrn_reflns_theta_min         4.442
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.9283
_exptl_absorpt_correction_T_min  0.7896
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
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_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.495
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_refine_diff_density_max         0.232
_refine_diff_density_min         -0.148
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_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   -0.01(4)
_refine_ls_extinction_coef       0.0091(6)
_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   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0267
_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^)+(0.0378P)^2^+0.2304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3169
_reflns_number_total             3236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02620a2.cif
_cod_data_source_block           wsj024
_cod_depositor_comments
'Adding full bibliography for 7133234--7133235.cif.'
_cod_database_code               7133234
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.722
_shelx_estimated_absorpt_t_max   0.858
_shelx_res_checksum              43082
_shelx_hkl_checksum              19927