Access to Chiral Tetrahydrofluorenes through Palladium-Catalyzed Enantioselective Tandem Intramolecular Heck/Tsuji–Trost Reaction
Zhang, Ying; Shen, Hong-Cheng; Li, Yang-Yang; Huang, Yong-Shuang; Han, Zhiyong; Wu, Xiang; Chemical Communications  (2019) –; doi:10.1039/C9CC01379B

data_7123082
_publ_section_title
;
 Access to Chiral Tetrahydrofluorenes through Palladium-Catalyzed
 Enantioselective Tandem Intramolecular Heck/Tsuji--Trost Reaction
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01379B
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C28 H23 Br3 N2 O2, H2 O'
_chemical_formula_sum            'C28 H25 Br3 N2 O3'
_chemical_formula_weight         677.23
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2138xc
_audit_creation_date             2018-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-20 deposited with the CCDC.    2019-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.688(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4998(9)
_cell_length_b                   23.790(3)
_cell_length_c                   7.8325(9)
_cell_measurement_reflns_used    2520
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.32
_cell_measurement_theta_min      2.65
_cell_volume                     1373.2(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11233
_diffrn_reflns_point_group_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_min         1.712
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.438
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1195 before and 0.0686 after correction. The Ratio of minimum to maximum transmission is 0.5715. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 999 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.722
_reflns_Friedel_fraction_max     0.713
_reflns_number_gt                3329
_reflns_number_total             5403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01379b2.cif
_cod_data_source_block           mo_dm18076_0m
_cod_database_code               7123082
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.618
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1S(H1SA,H1SB)
2.b Ternary CH refined with riding coordinates:
 C1(H1A), C11(H11)
2.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C3(H3A,H3B), C21(H21A,H21B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C8(H8), C27(H27), C28(H28), C13(H13), C24(H24), C16(H16),
 C17(H17), C20(H20), C25(H25), C6(H6), C12(H12), C19(H19), C5(H5)
;
_shelx_res_checksum              94977
_olex2_submission_special_instructions 'No special instructions were received'