Highly regio- and stereoselective (3 + 2) annulation reaction of allenoates with 3-methyleneindolin-2-ones catalyzed by a planar chiral [2.2]paracyclophane-based bifunctional phosphine-phenol catalyst.
Kitagaki, Shinji; Nakayoshi, Tomoki; Masunaka, Sota; Uchida, Akane; Inano, Mai; Yoshida, Emika; Washino, Yusuke; Aoyama, Hiroshi; Yoshida, Keisuke; Organic & biomolecular chemistry 22 (2024) 7817–7833; doi:10.1039/d4ob00831f

data_7160051
_publ_section_title
;
 Highly regio- and stereoselective (3 + 2) annulation reaction of
 allenoates with 3-methyleneindolin-2-ones catalyzed by a planar chiral
 [2.2]paracyclophane-based bifunctional phosphine-phenol catalyst.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7817
_journal_page_last               7833
_journal_paper_doi               10.1039/d4ob00831f
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C38 H37 O P'
_chemical_formula_sum            'C38 H37 O P'
_chemical_formula_weight         540.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-03-28 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.211(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.79364(19)
_cell_length_b                   10.5919(2)
_cell_length_c                   14.5081(3)
_cell_measurement_reflns_used    15923
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.06
_cell_volume                     1498.75(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15526
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.221
_diffrn_reflns_theta_min         3.059
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  0.443
_exptl_absorpt_correction_T_min  0.336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576.00
_exptl_crystal_size_max          0.830
_exptl_crystal_size_mid          0.810
_exptl_crystal_size_min          0.800
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.41
_refine_ls_abs_structure_details
;
 Flack x determined using 2151 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5305
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.045
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0723P)^2^+0.1487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                5125
_reflns_number_total             5305
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d4ob00831f3.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7160051--7160053.cif.'
_cod_original_cell_volume        1498.76(5)
_cod_database_code               7160051
_shelx_res_checksum              84540