Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki‒Miyaura Coupling Reactions
Benhamou, Laure; Besnard, Céline; Kündig, E. Peter; Organometallics 33 (2014) 260–; doi:10.1021/om4009982

data_4082558
_publ_section_title
;
 Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in
 Asymmetric Suzuki--Miyaura Coupling Reactions
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              260
_journal_paper_doi               10.1021/om4009982
_journal_volume                  33
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H40 Cl I2 N3 Pd'
_chemical_formula_sum            'C38 H40 Cl I2 N3 Pd'
_chemical_formula_weight         934.38
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-09-23
_audit_creation_method
;
  Olex2 1.1-alpha
  (compiled 2011.08.21 svn.r1945, GUI svn.r3824)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.5304(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.21749(8)
_cell_length_b                   18.33429(17)
_cell_length_c                   10.64812(10)
_cell_measurement_reflns_used    10452
_cell_measurement_temperature    180.1
_cell_measurement_theta_max      73.2733
_cell_measurement_theta_min      4.1486
_cell_volume                     1799.41(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.1
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega  -68.00   39.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6865   38.0000 -180.0000 107

  2 omega   24.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       37.6865 -102.0000  127.0000 52

  3 omega   41.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000    0.0000 36

  4 omega  119.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  111.0000  150.0000 58

  5 omega   40.00   67.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000 -120.0000 27

  6 omega   61.00  103.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -77.0000  -60.0000 42

  7 omega   38.00  152.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499    0.0000   90.0000 114

  8 omega -117.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6865  -38.0000  120.0000 111

  9 omega -122.00   -2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6865  -77.0000   60.0000 120

 10 omega   29.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   15.0000  -60.0000 149

 11 omega   79.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   45.0000  120.0000 99

 12 omega   31.00   70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000   60.0000 39

 13 omega   27.00  113.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -105.0000 -141.0000 86

 14 omega  -68.00   39.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6865   38.0000 -180.0000 107

 15 omega   24.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6865 -102.0000  127.0000 52

 16 omega  -71.00   11.00   1.0000    2.6700
omega____ theta____ kappa____ phi______ frames
    -      -37.6865  102.0000 -127.0000 82

 17 omega   92.00  133.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -77.0000  -30.0000 41

 18 omega  108.00  134.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -77.0000  150.0000 26

 19 omega  -51.00  -25.00   1.0000    2.6700
omega____ theta____ kappa____ phi______ frames
    -      -37.6865   77.0000   30.0000 26

 20 omega   21.00   46.00   1.0000    2.6700
omega____ theta____ kappa____ phi______ frames
    -      -37.6865   77.0000   30.0000 25

 21 omega   45.00   75.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000   90.0000 30

 22 omega   97.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -128.0000   52.0000 26

 23 omega   87.00  113.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -128.0000 -127.0000 26

 24 omega  -31.00   -6.00   1.0000    2.6700
omega____ theta____ kappa____ phi______ frames
    -      -37.6865  -38.0000    0.0000 25

 25 omega   31.00   56.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000  120.0000 25

 26 omega   34.00   63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000  -60.0000 29
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0471843000
_diffrn_orient_matrix_UB_12      -0.0806073000
_diffrn_orient_matrix_UB_13      0.0004262000
_diffrn_orient_matrix_UB_21      -0.0085360000
_diffrn_orient_matrix_UB_22      0.0016887000
_diffrn_orient_matrix_UB_23      0.1443431000
_diffrn_orient_matrix_UB_31      -0.1602209000
_diffrn_orient_matrix_UB_32      0.0236175000
_diffrn_orient_matrix_UB_33      -0.0089176000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14342
_diffrn_reflns_theta_full        73.43
_diffrn_reflns_theta_max         73.43
_diffrn_reflns_theta_min         4.15
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    18.540
_exptl_absorpt_correction_T_max  0.711
_exptl_absorpt_correction_T_min  0.398
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.1633
_exptl_crystal_size_mid          0.0525
_exptl_crystal_size_min          0.0406
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.007(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         6647
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.3271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0714
_reflns_number_gt                6507
_reflns_number_total             6647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4009982_si_002.cif
_cod_data_source_block           lb1
_cod_database_code               4082558
_chemical_oxdiff_formula         'c38 H40 Cl1 I2 N3 Pd1'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97