π-Coordinating Chiral Primary Amine/Palladium Synergistic Catalysis for Asymmetric Allylic Alkylation.
Wang, Yaning; Chai, Junli; You, Chang; Zhang, Jie; Mi, Xueling; Zhang, Long; Luo, Sanzhong; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b13026

data_4134090
_publ_section_title
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 \p-Coordinating Chiral Primary Amine/Palladium Synergistic Catalysis for
 Asymmetric Allylic Alkylation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13026
_journal_year                    2020
_chemical_formula_moiety         '2(C21.05 H29 N2 Pd), 2(C F3 O3 S), C H2 Cl2'
_chemical_formula_sum            'C45.17 H60 Cl2 F6 N4 O6 Pd2 S2'
_chemical_formula_weight         1216.83
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
????
;
_cell_angle_alpha                106.417(14)
_cell_angle_beta                 110.789(12)
_cell_angle_gamma                93.976(15)
_cell_formula_units_Z            1
_cell_length_a                   9.365(3)
_cell_length_b                   11.859(3)
_cell_length_c                   13.177(3)
_cell_measurement_reflns_used    4833
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4826
_cell_measurement_theta_min      1.7508
_cell_volume                     1288.7(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_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      173.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15424
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.751
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.77968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       block
_exptl_crystal_F_000             619
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.326
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5875
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0748
_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^)+(0.0327P)^2^+9.3047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5544
_reflns_number_total             5875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b13026_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        1288.6(6)
_cod_database_code               4134090
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.878
_shelx_estimated_absorpt_t_min   0.862
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C16A-C15A = C18A-C15A = C17A-C15A
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C15 \\sim C16 \\sim C17 \\sim C18 \\sim C15A \\sim C16A \\sim C17A \\sim C18A:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(N2A)=Sof(H2AA)=Sof(H2AB)=Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=
 Sof(H14A)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17A)=Sof(H17D)=
 Sof(H17E)=Sof(H17F)=Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(N2)=Sof(H2A)=Sof(H2B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
 Fixed Sof: C22(0.5) H22A(0.5) H22B(0.5)
5.a Riding coordinates:
 C20(H20)
5.b Ternary CH refined with riding coordinates:
 C14(H14), C14A(H14A)
5.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C19(H19A,H19B), C21(H21A,H21B), N2(H2A,H2B),
 C13(H13A,H13B), N2A(H2AA,H2AB), C13A(H13C,H13D), C22(H22A,H22B)
5.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9)
5.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16A(H16D,H16E,
 H16F), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F)
;
_shelx_res_checksum              60668
_shelx_hkl_checksum              49527
_olex2_submission_special_instructions 'No special instructions were received'