Buchwald-Hartwig amination using Pd(i) dimer precatalysts supported by biaryl phosphine ligands.
Kirlikovali, Kent O.; Cho, Eunho; Downard, Tyler J.; Grigoryan, Lilit; Han, Zheng; Hong, Sooji; Jung, Dahee; Quintana, Jason C.; Reynoso, Vanessa; Ro, Sooihk; Shen, Yi; Swartz, Kevin; Ter Sahakyan, Elizabeth; Wixtrom, Alex I.; Yoshida, Brandon; Rheingold, Arnold L.; Spokoyny, Alexander M.; Dalton transactions (Cambridge, England : 2003) 47 (2018) 3684–3688; doi:10.1039/c8dt00119g

data_7045616
_publ_section_title
;
 Buchwald-Hartwig amination using Pd(i) dimer precatalysts supported by
 biaryl phosphine ligands.
;
_journal_issue                   11
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3684
_journal_page_last               3688
_journal_paper_doi               10.1039/c8dt00119g
_journal_volume                  47
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C60 H86 O4 P2 Pd2, 3(C2 H4 Cl2), 2(B F4)'
_chemical_formula_sum            'C66 H98 B2 Cl6 F8 O4 P2 Pd2'
_chemical_formula_weight         1616.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-19 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0268(14)
_cell_length_b                   16.0162(9)
_cell_length_c                   21.3417(12)
_cell_measurement_reflns_used    7139
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.012
_cell_measurement_theta_min      2.315
_cell_volume                     7187.2(7)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.1135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32553
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_min         1.590
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  0.2602
_exptl_absorpt_correction_T_min  0.2101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1162 before and 0.0928 after correction. The Ratio of minimum to maximum transmission is 0.8075. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             3328
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.29(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     833
_refine_ls_number_reflns         13353
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0295P)^2^+6.9805P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                11284
_reflns_number_total             13353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt00119g2.cif
_cod_data_source_block           spok74_a
_cod_depositor_comments
'Adding full bibliography for 7045616--7045618.cif.'
_cod_database_code               7045616
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.907
_shelx_estimated_absorpt_t_min   0.800
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.71(4)
 0.29(4)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C65) = Uanis(Cl5)
4. Others
 Sof(C66')=Sof(H66C)=Sof(H66D)=Sof(C65')=Sof(H65C)=Sof(H65D)=1-FVAR(1)
 Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(C66)=Sof(H66A)=Sof(H66B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C49(H49), C23(H23), C19(H19), C16(H16), C31(H31), C55(H55), C13(H13), C37(H37)
5.b Secondary CH2 refined with riding coordinates:
 C60(H60A,H60B), C32(H32A,H32B), C59(H59A,H59B), C33(H33A,H33B), C38(H38A,
 H38B), C54(H54A,H54B), C51(H51A,H51B), C52(H52A,H52B), C50(H50A,H50B),
 C63(H63A,H63B), C58(H58A,H58B), C53(H53A,H53B), C62(H62A,H62B), C61(H61A,H61B),
  C57(H57A,H57B), C39(H39A,H39B), C40(H40A,H40B), C56(H56A,H56B), C41(H41A,
 H41B), C42(H42A,H42B), C34(H34A,H34B), C36(H36A,H36B), C64(H64A,H64B),
 C35(H35A,H35B), C65(H65A,H65B), C66(H66A,H66B), C66'(H66C,H66D), C65'(H65C,
 H65D)
5.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C29(H29), C6(H6), C2(H2), C11(H11), C44(H44), C9(H9), C27(H27),
 C45(H45), C26(H26), C1(H1), C10(H10), C47(H47), C46(H46)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C17(H17A,H17B,
 H17C), C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C15(H15A,H15B,H15C), C24(H24A,
 H24B,H24C)
;
_shelx_res_checksum              91492
_olex2_submission_special_instructions 'No special instructions were received'