Palladium-catalyzed enantioselective C(sp<sup>2</sup>)-H arylation of ferrocenyl ketones enabled by a chiral transient directing group.
Xu, Jiancong; Liu, Yang; Zhang, Jinling; Xu, Xiaohua; Jin, Zhong; Chemical communications (Cambridge, England) 54 (2018) 689–692; doi:10.1039/c7cc09273c

data_7121035
_publ_section_title
;
 Palladium-catalyzed enantioselective C(sp<sup>2</sup>)-H arylation of
 ferrocenyl ketones enabled by a chiral transient directing group.
;
_journal_issue                   6
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              689
_journal_page_last               692
_journal_paper_doi               10.1039/c7cc09273c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C32 H28 Fe N O3 P Pd, 3(C H Cl3)'
_chemical_formula_sum            'C35 H31 Cl9 Fe N O3 P Pd'
_chemical_formula_weight         1025.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-21 deposited with the CCDC.
2017-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                98.08(3)
_cell_angle_beta                 104.26(3)
_cell_angle_gamma                105.36(3)
_cell_formula_units_Z            2
_cell_length_a                   11.649(2)
_cell_length_b                   12.431(3)
_cell_length_c                   15.066(3)
_cell_measurement_reflns_used    6071
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.9
_cell_volume                     1988.9(9)
_computing_cell_refinement       'CrystaClear(Rigaku, 2008)'
_computing_data_collection       'CrystaClear(Rigaku, 2008)'
_computing_data_reduction        'CrystaClear(Rigaku, 2008)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23895
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.873
_diffrn_reflns_theta_min         1.430
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    1.498
_exptl_absorpt_correction_T_max  0.7967
_exptl_absorpt_correction_T_min  0.7354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystaClear(Rigaku, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.219
_refine_ls_extinction_coef       0.0175(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         9425
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0795P)^2^+1.4559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8046
_reflns_number_total             9425
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09273c2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 7121034--7121035.cif.'
_cod_original_cell_volume        1988.8(8)
_cod_database_code               7121035
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.795
_shelx_estimated_absorpt_t_min   0.734
_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. Restrained distances
 Cl7-C35 = Cl8-C35 = Cl9-C35
 1.72 with sigma of 0.01
 Cl7A-C35A = Cl8A-C35A = Cl9A-C35A
 1.72 with sigma of 0.01
 Cl7-Cl8 \\sim Cl7-Cl9 \\sim Cl8-Cl9 \\sim Cl7A-Cl8A \\sim Cl7A-Cl9A \\sim
Cl8A-Cl9A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(Cl7) \\sim Ueq, Uanis(Cl8) \\sim Ueq, Uanis(Cl9) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C35) = Uanis(C35A)
Uanis(Cl7) = Uanis(Cl7A)
Uanis(Cl8) = Uanis(Cl8A)
Uanis(Cl9) = Uanis(Cl9A)
4. Others
 Sof(Cl9A)=Sof(Cl7A)=Sof(Cl8A)=Sof(C35A)=Sof(H35A)=1-FVAR(1)
 Sof(Cl7)=Sof(Cl8)=Sof(Cl9)=Sof(C35)=Sof(H35)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C33(H33), C34(H34), C35(H35), C35A(H35A)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
5.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              27282
_shelx_hkl_checksum              17271
_olex2_submission_special_instructions 'No special instructions were received'