Sequential oxidative dearomatization/asymmetric homologation: from simple naphthols to chiral benzocycloheptanes.
Zeng, Hongkun; Li, Shiyang; Ning, Lichao; Huang, Tao; Feng, Xiaoming; Lin, Lili; Chemical science 16 (2025) 22536–22541; doi:10.1039/d5sc05865a

data_1576036
_publ_section_title
;
 Sequential oxidative dearomatization/asymmetric homologation: from simple
 naphthols to chiral benzocycloheptanes.
;
_journal_issue                   47
_journal_name_full               'Chemical science'
_journal_page_first              22536
_journal_page_last               22541
_journal_paper_doi               10.1039/d5sc05865a
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H24 N2 O2'
_chemical_formula_sum            'C32 H24 N2 O2'
_chemical_formula_weight         468.53
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2025-03-08 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.46440(10)
_cell_length_b                   11.46440(10)
_cell_length_c                   37.6131(7)
_cell_measurement_reflns_used    9582
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.07
_cell_measurement_theta_min      4.03
_cell_volume                     4943.58(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX5'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0372
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            39667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_min         4.031
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.9143
_exptl_absorpt_correction_T_min  0.8066
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2016/2 (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       cube
_exptl_crystal_F_000             1968
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.234
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
; 
 Flack x determined using 1760 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_coef       0.00163(13)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0252
_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^)+(0.0365P)^2^+0.5007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0655
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4411
_reflns_number_total             4530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05865a2.cif
_cod_data_source_block           xuj025
_cod_depositor_comments          'Adding full bibliography for 1576036.cif.'
_cod_original_cell_volume        4943.58(13)
_cod_database_code               1576036
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.810
_shelx_estimated_absorpt_t_max   0.868
_shelx_res_checksum              41544