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_7123081
_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         'C33 H36 O4'
_chemical_formula_sum            'C33 H36 O4'
_chemical_formula_weight         496.62
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2138wb
_audit_creation_date             2018-09-17
_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                 96.5050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.83500(10)
_cell_length_b                   7.9694(2)
_cell_length_c                   24.6235(5)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.945
_cell_measurement_theta_min      3.14
_cell_volume                     1332.63(5)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16789
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.936
_diffrn_reflns_theta_min         4.718
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1622 before and 0.0811 after correction. The Ratio of minimum to maximum transmission is 0.6958. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2049 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4937
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0602P)^2^+0.2846P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                4781
_reflns_number_total             4937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01379b2.cif
_cod_data_source_block           mjl18438_0m
_cod_database_code               7123081
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.942
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C12(H12), C19(H19), C20(H20), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C13(H13A,H13B), C17(H17A,H17B), C18(H18A,H18B), C26(H26A,H26B),
 C27(H27A,H27B), C29(H29A,H29B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              61879
_olex2_submission_special_instructions 'No special instructions were received'