Catalytic asymmetric P<sup>(III)</sup>-additions to salicylaldehydes enable divergent stereoselective dearomatizations of phenols.
Clarkson, Aidan J.; Alley, Kimberly A.; Werley, Bryn K.; Robins, Jacob G.; Liu, Shubin; Johnson, Jeffrey S.; Chemical science 17 (2026) 2837–2846; doi:10.1039/d5sc08571c

data_1576732
_publ_section_title
;
 Catalytic asymmetric P<sup>(III)</sup>-additions to salicylaldehydes
 enable divergent stereoselective dearomatizations of phenols.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              2837
_journal_page_last               2846
_journal_paper_doi               10.1039/d5sc08571c
_journal_volume                  17
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H26 Br4 Cl2.00 Cu1 N2 O6'
_chemical_formula_sum            'C38 H26 Br4 Cl2 Cu N2 O6'
_chemical_formula_weight         1060.70
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2025-07-23
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_audit_update_record
;
2025-07-23 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.2220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8594(5)
_cell_length_b                   8.1479(4)
_cell_length_c                   21.4301(8)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    150
_cell_measurement_theta_max      52
_cell_measurement_theta_min      5
_cell_volume                     1896.15(15)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.084
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            63030
_diffrn_reflns_theta_full        26.075
_diffrn_reflns_theta_max         26.075
_diffrn_reflns_theta_min         2.099
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.981
_exptl_absorpt_correction_T_max  0.61
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1038.000
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.11
_refine_diff_density_min         -1.13
_refine_ls_abs_structure_details 'Flack (1983), 3471 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.025(14)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         7456
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.0315694
_refine_ls_shift/su_mean         0.0003855
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.09P)^2^ + 4.30P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1495
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1495
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                6364
_reflns_number_total             7481
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.52
_oxford_diffrn_Wilson_scale      4.96
_oxford_refine_ls_r_factor_ref   0.0621
_oxford_refine_ls_scale          0.3836(6)
_oxford_reflns_number_all        7456
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 'mo_22011_a.res in P2(1)'
_cod_data_source_file            d5sc08571c2.cif
_cod_data_source_block           22011
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C38 H26 Br4 Cl2.00 Cu1 N2 O6'
_cod_database_code               1576732