Enantioconvergent synthesis of chiral fluorenols from racemic secondary alcohols <i>via</i> Pd(ii)/chiral norbornene cooperative catalysis.
Ding, Bo; Xue, Qilin; Wei, Han; Chen, Jiangwei; Liu, Ze-Shui; Cheng, Hong-Gang; Cong, Hengjiang; Tang, Jianting; Zhou, Qianghui; Chemical science 15 (2024) 7975–7981; doi:10.1039/d4sc01004c

data_1571490
_publ_section_title
;
 Enantioconvergent synthesis of chiral fluorenols from racemic secondary
 alcohols <i>via</i> Pd(ii)/chiral norbornene cooperative catalysis.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              7975
_journal_page_last               7981
_journal_paper_doi               10.1039/d4sc01004c
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 O'
_chemical_formula_sum            'C22 H20 O'
_chemical_formula_weight         300.38
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-28 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7777(3)
_cell_length_b                   8.0764(3)
_cell_length_c                   25.7905(9)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      65.23
_cell_measurement_theta_min      3.43
_cell_volume                     1620.05(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19056
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        65.219
_diffrn_reflns_theta_max         65.219
_diffrn_reflns_theta_min         3.427
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_coef       0.0078(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0504P)^2^+0.2955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0881
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2758
_reflns_number_total             2770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01004c2.cif
_cod_data_source_block           x
_cod_depositor_comments
'Adding full bibliography for 1571490--1571491.cif.'
_cod_database_code               1571490
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C20(H20), C3(H3), C7(H7), C17(H17), C8(H8), C19(H19), C18(H18),
 C2(H2), C1(H1A)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              56761
_olex2_submission_special_instructions 'No special instructions were received'