Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos).
Rodstein, Ilja; Prendes, Daniel Sowa; Wickert, Leon; Paaßen, Maurice; Gessner, Viktoria; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01771

data_4038812
_publ_section_title
;
 Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines
 through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos).
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01771
_journal_year                    2020
_chemical_formula_sum            'C38 H62 P2'
_chemical_formula_weight         580.81
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.3613(9)
_cell_angle_gamma                90
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_cell_length_b                   20.32473(18)
_cell_length_c                   16.76223(15)
_cell_measurement_reflns_used    12931
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.8930
_cell_measurement_theta_min      3.4440
_cell_volume                     3448.63(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
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_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -20
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_diffrn_reflns_limit_l_min       -21
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_max         76.896
_diffrn_reflns_theta_min         3.452
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.301
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018)
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            'clear light colourless'
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     427
_refine_ls_number_reflns         6991
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0479P)^2^+1.2673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6329
_reflns_number_total             6991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01771_si_009.cif
_cod_data_source_block           IR-033_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038812
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              49480
_shelx_hkl_checksum              71616