Enantioselective Desymmetrization of Bisphenol Derivatives via Ir-Catalyzed Allylic Dearomatization.
Wang, Ye; Zhang, Wen-Yun; Xie, Jia-Hao; Yu, Zong-Lun; Tan, Jia-Hao; Zheng, Chao; Hou, Xue-Long; You, Shu-Li; Journal of the American Chemical Society 142 (2020) 19354–19359; doi:10.1021/jacs.0c09638

data_4135332
_publ_section_title
;
 Enantioselective Desymmetrization of Bisphenol Derivatives via
 Ir-Catalyzed Allylic Dearomatization.
;
_journal_issue                   45
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19354
_journal_page_last               19359
_journal_paper_doi               10.1021/jacs.0c09638
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C29 H33 N O4 S'
_chemical_formula_sum            'C29 H33 N O4 S'
_chemical_formula_weight         491.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   39.5169(7)
_cell_length_b                   11.9534(2)
_cell_length_c                   12.6942(2)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.82
_cell_measurement_theta_min      3.182
_cell_volume                     5996.25(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.97
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            55269
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.954
_diffrn_reflns_theta_min         3.029
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0997 before and 0.0729 after correction. The Ratio of minimum to maximum transmission is 0.7852. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 3408 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.070(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     643
_refine_ls_number_reflns         11376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+1.1739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                9251
_reflns_number_total             11376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09638_si_002.cif
_cod_data_source_block           mjl18549
_cod_depositor_comments
'Adding full bibliography for 4135332--4135333.cif.'
_cod_database_code               4135332
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.800
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A), C1A(H1A), C2A(H2AB)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C3A(H3AA,H3AB), C4A(H4AA,H4AB)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C13(H13), C16(H16), C20(H20), C24(H24), C25(H25), C27(H27),
 C28(H28), C6A(H6A), C10A(H10A), C13A(H13A), C16A(H16A), C20A(H20A), C24A(H24A),
  C25A(H25A), C27A(H27A), C28A(H28A)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B), C14A(H14C,H14D)
2.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C29(H29A,H29B,H29C), C11A(H11D,H11E,H11F), C12A(H12D,H12E,H12F),
 C21A(H21D,H21E,H21F), C22A(H22D,H22E,H22F), C29A(H29D,H29E,H29F)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2A(H2AA)
;
_shelx_res_checksum              90358
_shelx_hkl_checksum              64075
_shelx_fab_checksum              74432
_olex2_submission_special_instructions 'No special instructions were received'