Exploiting the gem-Disubstitution Effect in FcPHOX and HetPHOX P,N Ligands: Synthesis and Applications in Pd-Catalyzed Intermolecular Heck Reactions.
McCartney, Dennis; Nottingham, Chris; Müller-Bunz, Helge; Guiry, Patrick J.; The Journal of organic chemistry 80 (2015) 10151–10162; doi:10.1021/acs.joc.5b01764

data_4036370
_publ_section_title
;
 Exploiting the gem-Disubstitution Effect in FcPHOX and HetPHOX P,N
 Ligands: Synthesis and Applications in Pd-Catalyzed Intermolecular Heck
 Reactions.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10151
_journal_page_last               10162
_journal_paper_doi               10.1021/acs.joc.5b01764
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2 (C34 H30 Cl2 N O P Pd S), 3 (C H Cl3)'
_chemical_formula_sum            'C71 H63 Cl13 N2 O2 P2 Pd2 S2'
_chemical_formula_weight         1775.94
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5741(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.7993(2)
_cell_length_b                   9.89370(10)
_cell_length_c                   22.8314(3)
_cell_measurement_reflns_used    32683
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.6350
_cell_measurement_theta_min      3.4400
_cell_volume                     3730.30(8)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'supernova, dual, cu at zero, atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'supernova (mo) x-ray source'
_diffrn_radiation_type           mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            45053
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.75
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
crysalispro, agilent technologies, 
version 1.171.36.24a (release 19-12-2012 crysalis171 .net) 
(compiled dec 19 2012,11:08:27) 
analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by r.c. clark & j.s. reid. 
(clark, r. c. & reid, j. s. (1995). acta cryst. a51, 887-897) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1788
_exptl_crystal_size_max          0.2099
_exptl_crystal_size_mid          0.1488
_exptl_crystal_size_min          0.0692
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.030(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         12790
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0168
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0183P)^2^+1.6109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0396
_refine_ls_wR_factor_ref         0.0400
_reflns_number_gt                12547
_reflns_number_total             12790
_reflns_threshold_expression     i>2\s(i)
_cod_data_source_file            jo5b01764_si_001.cif
_cod_data_source_block           gui63(32)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4036370