Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization.
O'Duill, Miriam L; Matsuura, Rei; Wang, Yanyan; Turnbull, Joshua L.; Gurak, Jr, John A; Gao, De-Wei; Lu, Gang; Liu, Peng; Engle, Keary M.; Journal of the American Chemical Society 139 (2017) 15576–15579; doi:10.1021/jacs.7b08383

data_4131670
_publ_section_title
;
 Tridentate Directing Groups Stabilize 6-Membered Palladacycles in
 Catalytic Alkene Hydrofunctionalization.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15576
_journal_page_last               15579
_journal_paper_doi               10.1021/jacs.7b08383
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         '2(C17 H17 N3 O3 Pd), H2 O'
_chemical_formula_sum            'C34 H36 N6 O7 Pd2'
_chemical_formula_weight         853.49
_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
_audit_creation_date             2017-05-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                81.916(3)
_cell_angle_beta                 86.459(2)
_cell_angle_gamma                69.010(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5111(5)
_cell_length_b                   10.9386(6)
_cell_length_c                   19.1791(10)
_cell_measurement_reflns_used    2211
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.34
_cell_measurement_theta_min      32.38
_cell_volume                     1650.39(16)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_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  0.0425
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22119
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.330
_diffrn_reflns_theta_min         2.327
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.288
_exptl_absorpt_correction_T_max  0.1665
_exptl_absorpt_correction_T_min  0.0569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0876 before and 0.0583 after correction. The Ratio of minimum to maximum transmission is 0.3417. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_description       needle
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         5925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+1.4878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5349
_reflns_number_total             5925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b08383_si_004.cif
_cod_data_source_block           engle35_0m_a
_cod_database_code               4131670
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.563
_shelx_estimated_absorpt_t_min   0.174
_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, All O(H,H) groups
2.a Free rotating group:
 O7(H7A,H7B)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C20(H20A,H20B), C21(H21A,H21B)
2.c Me refined with riding coordinates:
 C34(H34A,H34B,H34C)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C24(H24), C25(H25), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32)
2.e X=CH2 refined with riding coordinates:
 C1(H1A,H1B), C18(H18A,H18B)
2.f Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'