Pd(II)-Catalyzed Asymmetric Annulation towards the Synthesis of 2,3-Disubstituted Chiral Indenols.
Gu, Chang-Xue; Chen, Wen-Wen; Xu, Ming-Hua; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b02958

data_4037874
_publ_section_title
;
 Pd(II)-Catalyzed Asymmetric Annulation towards the Synthesis of
 2,3-Disubstituted Chiral Indenols.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02958
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H15 F O'
_chemical_formula_sum            'C21 H15 F O'
_chemical_formula_weight         302.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.947(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.769(2)
_cell_length_b                   5.4256(4)
_cell_length_c                   11.0130(8)
_cell_measurement_reflns_used    6757
_cell_measurement_temperature    173
_cell_measurement_theta_max      70.960
_cell_measurement_theta_min      3.386
_cell_volume                     1559.7(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8291
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        63.674
_diffrn_reflns_theta_max         63.674
_diffrn_reflns_theta_min         3.386
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.6043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1200 before and 0.0576 after correction. The Ratio of minimum to maximum transmission is 0.8021. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0580P)^2^+0.3080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.853
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                2316
_reflns_number_total             2383
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02958_si_002.cif
_cod_data_source_block           cu_2017843_0m
_cod_database_code               4037874
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.723
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C15(H15), C20(H20), C19(H19), C11(H11), C21(H21), C1(H1A),
  C14(H14), C4(H4), C12(H12), C13(H13), C2(H2)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'