Chiral cobalt(ii) complex-promoted asymmetric <i>para</i>-Claisen rearrangement of allyl α-naphthol ethers.
Zeng, Hongkun; Wang, Lifeng; Su, Zhishan; Ying, Meijia; Lin, Lili; Feng, Xiaoming; Chemical science 14 (2023) 13979–13985; doi:10.1039/d3sc05677e

data_1570377
_publ_section_title
;
 Chiral cobalt(ii) complex-promoted asymmetric <i>para</i>-Claisen
 rearrangement of allyl &#x3b1;-naphthol ethers.
;
_journal_issue                   47
_journal_name_full               'Chemical science'
_journal_page_first              13979
_journal_page_last               13985
_journal_paper_doi               10.1039/d3sc05677e
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H26 O3'
_chemical_formula_sum            'C31 H26 O3'
_chemical_formula_weight         446.52
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-08-21 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.83070(10)
_cell_length_b                   15.5594(3)
_cell_length_c                   21.1844(4)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.52
_cell_volume                     2581.13(8)
_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-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0681
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16167
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.265
_diffrn_reflns_theta_min         3.524
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6345
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       flake
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
; 
 Flack x determined using 1792 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4717
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0672
_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^)+(0.1072P)^2^+0.6656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1697
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4449
_reflns_number_total             4717
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05677e2.cif
_cod_data_source_block           wsj025
_cod_depositor_comments
'Adding full bibliography for 1570376--1570377.cif.'
_cod_database_code               1570377
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.806
_shelx_estimated_absorpt_t_max   0.945
_shelx_res_checksum              98856
_shelx_hkl_checksum              15913