Synthetic and Mechanistic Interrogation of Pd/Isocyanide-Catalyzed Cross-Coupling: π-Acidic Ligands Enable Self-Aggregating Monoligated Pd(0) Intermediates
Barnett, Brandon R.; Labios, Liezel A.; Stauber, Julia M.; Moore, Curtis E.; Rheingold, Arnold L.; Figueroa, Joshua S.; Organometallics 36 (2017) 944–; doi:10.1021/acs.organomet.7b00035

data_4087104
_publ_section_title
;
 Synthetic and Mechanistic Interrogation of Pd/Isocyanide-Catalyzed
 Cross-Coupling: \p-Acidic Ligands Enable Self-Aggregating Monoligated
 Pd(0) Intermediates
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              944
_journal_paper_doi               10.1021/acs.organomet.7b00035
_journal_volume                  36
_journal_year                    2017
_chemical_formula_moiety         'C93 H111 N3 Pd3, 13(C4H8O)'
_chemical_formula_sum            'C145 H215 N3 O13 Pd3'
_chemical_formula_weight         2527.39
_chemical_name_common            Pd3(eta2-Dipp-u-CNArDipp2)3
_space_group_crystal_system      trigonal
_space_group_IT_number           165
_space_group_name_Hall           '-P 3 2"c'
_space_group_name_H-M_alt        'P -3 c 1'
_symmetry_space_group_name_Hall  '-P 3 2"c'
_symmetry_space_group_name_H-M   'P -3 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-23
_audit_creation_method
;
Olex2 1.2
(compiled Jan 19 2015 12:28:14 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            4
_cell_length_a                   18.1967(5)
_cell_length_b                   18.1967(5)
_cell_length_c                   45.5371(16)
_cell_measurement_reflns_used    9784
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      65.91
_cell_measurement_theta_min      2.80
_cell_volume                     13058.1(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            136438
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.742
_diffrn_reflns_theta_max         66.741
_diffrn_reflns_theta_min         1.940
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.775
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             5392
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_platon_squeeze_details
;
SQUEEZE was used to account for 13 molecules of disordered
THF (C4H8O) per unit cell.
;
_refine_diff_density_max         1.211
_refine_diff_density_min         -0.969
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         7678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0331P)^2^+53.2456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6967
_reflns_number_total             7678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om7b00035_si_003.cif
_cod_data_source_block           jfigcu11_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        13058.1(9)
_cod_database_code               4087104
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.752
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(C1)
3.a Ternary CH refined with riding coordinates:
 C20(H20), C23(H23), C26(H26), C29(H29)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17),
 C18(H18)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,
 H31B,H31C)
;
_shelx_res_checksum              90971
_shelx_hkl_checksum              21498
_shelx_fab_checksum              15423
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'