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_4082559
_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 H42 Cl I2 N3 Pd'
_chemical_formula_sum            'C38 H42 Cl I2 N3 Pd'
_chemical_formula_weight         936.40
_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             2012-01-16
_audit_creation_method
;
  Olex2 1.2-alpha
  (compiled Jan 11 2012 18:49:03, GUI svn.r4030)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.3700(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.17840(10)
_cell_length_b                   18.4176(2)
_cell_length_c                   10.70510(10)
_cell_measurement_reflns_used    21311
_cell_measurement_temperature    190.00(14)
_cell_measurement_theta_max      29.1809
_cell_measurement_theta_min      2.1965
_cell_volume                     1809.12(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      190.00(14)
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
  1 omega   -1.00   55.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8786  -99.0000   60.0000 56

  2 omega  -12.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8786   57.0000 -120.0000 107

  3 omega  -37.00  -11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8786  -19.0000 -150.0000 26

  4 omega    3.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8786  -19.0000 -150.0000 69

  5 omega  -72.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8786  -77.0000  150.0000 112

  6 omega -108.00  -57.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.8630 -178.0000  150.0000 51

  7 omega   35.00   80.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.8630  178.0000  120.0000 45

  8 omega  -48.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.8630   57.0000 -180.0000 114

  9 omega  -65.00  -12.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8786  -57.0000  -30.0000 53

 10 omega  -19.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8786   57.0000   90.0000 114
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0223383000
_diffrn_orient_matrix_UB_12      -0.0321928000
_diffrn_orient_matrix_UB_13      -0.0313171000
_diffrn_orient_matrix_UB_21      -0.0065729000
_diffrn_orient_matrix_UB_22      0.0195208000
_diffrn_orient_matrix_UB_23      -0.0570025000
_diffrn_orient_matrix_UB_31      0.0737164000
_diffrn_orient_matrix_UB_32      -0.0080226000
_diffrn_orient_matrix_UB_33      -0.0128925000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31943
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         29.25
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         8891
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0202
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0184P)^2^+0.5419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0434
_reflns_number_gt                8462
_reflns_number_total             8891
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4009982_si_003.cif
_cod_data_source_block           laure_mo
_cod_database_code               4082559
_chemical_oxdiff_formula         'Pd1 N3 I2 Cl1 C38 H42'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32