Unraveling the High Activity of Ylide-Functionalized Phosphines in Palladium-Catalyzed Amination Reactions: A Comparative Study with CyJohnPhos and PtBu3
Scharf, Lennart T.; Rodstein, Ilja; Schmidt, Michelle; Scherpf, Thorsten; Gessner, Viktoria H.; ACS Catalysis  (2019) 999–; doi:10.1021/acscatal.9b04666

data_4517271
_publ_section_title
;
 Unraveling the High Activity of Ylide-Functionalized Phosphines in
 Palladium-Catalyzed Amination Reactions: A Comparative Study with
 CyJohnPhos and PtBu3
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              999
_journal_paper_doi               10.1021/acscatal.9b04666
_journal_year                    2019
_chemical_formula_moiety         'C39 H65 Cl P2 Pd, 2.5(C4 H8 O)'
_chemical_formula_sum            'C49 H85 Cl O2.5 P2 Pd'
_chemical_formula_weight         917.95
_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   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                116.403(2)
_cell_angle_beta                 99.017(2)
_cell_angle_gamma                106.380(2)
_cell_formula_units_Z            2
_cell_length_a                   11.8057(3)
_cell_length_b                   15.6134(3)
_cell_length_c                   15.6605(4)
_cell_measurement_reflns_used    17531
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      76.0410
_cell_measurement_theta_min      4.1010
_cell_volume                     2343.10(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4409
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34788
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.073
_diffrn_reflns_theta_min         3.336
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.645
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     572
_refine_ls_number_reflns         8891
_refine_ls_number_restraints     256
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0273
_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^)+(0.0402P)^2^+0.9924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0707
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8258
_reflns_number_total             8891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04666_si_002.cif
_cod_data_source_block           ST144
_cod_original_cell_volume        2343.10(11)
_cod_original_formula_sum        'C49 H85 Cl O2.50 P2 Pd'
_cod_database_code               4517271
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.556
_shelx_estimated_absorpt_t_max   0.885
_shelx_res_checksum              88418
_shelx_hkl_checksum              623