#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/37/1503719.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1503719
loop_
_publ_author_name
'Rubio-Pérez, Laura'
'Pérez-Flores, F Javier'
'Sharma, Pankaj'
'Velasco, Luis'
'Cabrera, Armando'
_publ_section_title
;
 Stable preformed chiral palladium catalysts for the one-pot asymmetric
 reductive amination of ketones.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              265
_journal_page_last               268
_journal_paper_doi               10.1021/ol802336m
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C44 H32 Br2 P2 Pd'
_chemical_formula_sum            'C44 H32 Br2 P2 Pd'
_chemical_formula_weight         888.86
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9124(3)
_cell_length_b                   11.9124(3)
_cell_length_c                   26.1910(13)
_cell_measurement_reflns_used    6233
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.72
_cell_measurement_theta_min      2.31
_cell_volume                     3716.6(2)
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 6.23A (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL V 6.12 (Sheldrick, 2000)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart APEX AXS CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            30513
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    2.767
_exptl_absorpt_correction_T_max  0.6659
_exptl_absorpt_correction_T_min  0.3895
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SHELXTL V 6.12 (Sheldrick, 2000)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1318 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.001(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0293
_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/[σ²(Fo²)+(0.0250P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0567
_refine_ls_wR_factor_ref         0.0578
_reflns_number_gt                2781
_reflns_number_total             3272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802336m_si_003.cif
_cod_data_source_block           100coa05
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'No' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               1503719
#BEGIN Tags that were not found in dictionaries:
_solved_by                       'Simon Hernandez-Ortega'
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Pd1 Pd -0.017858(19) 1.017858(19) 0.7500 0.03919(11) Uani 1 2 d S
Br1 Br -0.22300(3) 1.01361(4) 0.735350(19) 0.07400(17) Uani 1 1 d .
P1 P 0.14456(6) 0.99610(7) 0.79247(3) 0.0347(2) Uani 1 1 d .
C1 C 0.1997(3) 0.7695(3) 0.77672(12) 0.0339(8) Uani 1 1 d .
C2 C 0.1647(2) 0.8490(3) 0.81116(12) 0.0328(8) Uani 1 1 d .
C3 C 0.1348(3) 0.8155(3) 0.86143(14) 0.0472(9) Uani 1 1 d .
H3 H 0.1111 0.8690 0.8849 0.057 Uiso 1 1 calc R
C4 C 0.1404(4) 0.7060(3) 0.87549(15) 0.0603(11) Uani 1 1 d .
H4 H 0.1212 0.6861 0.9087 0.072 Uiso 1 1 calc R
C5 C 0.1766(4) 0.5069(4) 0.85490(18) 0.0844(15) Uani 1 1 d .
H5 H 0.1568 0.4852 0.8878 0.101 Uiso 1 1 calc R
C6 C 0.2067(5) 0.4291(4) 0.8209(2) 0.0916(18) Uani 1 1 d .
H6 H 0.2051 0.3538 0.8302 0.110 Uiso 1 1 calc R
C7 C 0.2402(4) 0.4583(3) 0.7720(2) 0.0818(15) Uani 1 1 d .
H7 H 0.2634 0.4030 0.7493 0.098 Uiso 1 1 calc R
C8 C 0.2391(3) 0.5677(3) 0.75716(17) 0.0570(11) Uani 1 1 d .
H8 H 0.2605 0.5864 0.7241 0.068 Uiso 1 1 calc R
C9 C 0.2059(3) 0.6536(3) 0.79134(13) 0.0426(9) Uani 1 1 d .
C10 C 0.1744(3) 0.6225(3) 0.84158(15) 0.0549(10) Uani 1 1 d .
C11 C 0.1345(3) 1.0736(3) 0.85211(13) 0.0448(9) Uani 1 1 d .
C12 C 0.0335(4) 1.0739(4) 0.87829(16) 0.0763(13) Uani 1 1 d .
H12 H -0.0266 1.0316 0.8663 0.092 Uiso 1 1 calc R
C13 C 0.0222(5) 1.1370(5) 0.9221(2) 0.1038(18) Uani 1 1 d .
H13 H -0.0458 1.1379 0.9395 0.125 Uiso 1 1 calc R
C14 C 0.1105(7) 1.1979(5) 0.9399(2) 0.107(2) Uani 1 1 d .
H14 H 0.1026 1.2398 0.9696 0.129 Uiso 1 1 calc R
C15 C 0.2094(5) 1.1982(3) 0.9148(2) 0.0792(14) Uani 1 1 d .
H15 H 0.2690 1.2405 0.9272 0.095 Uiso 1 1 calc R
C16 C 0.2222(4) 1.1365(3) 0.87118(15) 0.0553(11) Uani 1 1 d .
H16 H 0.2907 1.1369 0.8542 0.066 Uiso 1 1 calc R
C17 C 0.2732(3) 1.0398(3) 0.76226(12) 0.0387(8) Uani 1 1 d .
C18 C 0.2720(3) 1.0999(3) 0.71741(15) 0.0521(10) Uani 1 1 d .
H18 H 0.2039 1.1210 0.7029 0.063 Uiso 1 1 calc R
C19 C 0.3712(4) 1.1289(4) 0.69391(17) 0.0723(13) Uani 1 1 d .
H19 H 0.3700 1.1689 0.6634 0.087 Uiso 1 1 calc R
C20 C 0.4715(4) 1.0991(4) 0.71536(19) 0.0752(13) Uani 1 1 d .
H20 H 0.5382 1.1196 0.6994 0.090 Uiso 1 1 calc R
C21 C 0.4749(3) 1.0405(4) 0.75923(17) 0.0672(12) Uani 1 1 d .
H21 H 0.5438 1.0206 0.7733 0.081 Uiso 1 1 calc R
C22 C 0.3766(3) 1.0097(3) 0.78356(14) 0.0500(9) Uani 1 1 d .
H22 H 0.3792 0.9692 0.8139 0.060 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
P1 Pd1 P1 92.66(4) . 8_666
P1 Pd1 Br1 91.12(2) . 8_666
P1 Pd1 Br1 157.66(2) 8_666 8_666
P1 Pd1 Br1 157.66(2) . .
P1 Pd1 Br1 91.12(2) 8_666 .
Br1 Pd1 Br1 93.69(2) 8_666 .
C17 P1 C11 106.66(17) . .
C17 P1 C2 106.40(14) . .
C11 P1 C2 105.31(14) . .
C17 P1 Pd1 118.79(11) . .
C11 P1 Pd1 108.05(12) . .
C2 P1 Pd1 110.78(10) . .
C2 C1 C9 120.3(3) . .
C2 C1 C1 121.5(3) . 8_666
C9 C1 C1 118.3(3) . 8_666
C1 C2 C3 119.4(3) . .
C1 C2 P1 121.5(2) . .
C3 C2 P1 118.9(2) . .
C4 C3 C2 120.6(3) . .
C3 C4 C10 121.8(4) . .
C6 C5 C10 121.0(4) . .
C5 C6 C7 121.3(4) . .
C8 C7 C6 120.1(4) . .
C7 C8 C9 121.0(4) . .
C8 C9 C10 118.2(3) . .
C8 C9 C1 122.7(3) . .
C10 C9 C1 119.0(3) . .
C4 C10 C9 118.9(3) . .
C4 C10 C5 122.7(4) . .
C9 C10 C5 118.4(4) . .
C16 C11 C12 118.5(4) . .
C16 C11 P1 122.5(3) . .
C12 C11 P1 119.0(3) . .
C13 C12 C11 119.9(5) . .
C14 C13 C12 120.1(5) . .
C15 C14 C13 120.6(5) . .
C14 C15 C16 120.2(5) . .
C15 C16 C11 120.7(4) . .
C18 C17 C22 118.9(3) . .
C18 C17 P1 121.1(3) . .
C22 C17 P1 120.0(3) . .
C17 C18 C19 120.2(4) . .
C20 C19 C18 120.1(4) . .
C21 C20 C19 120.8(4) . .
C20 C21 C22 120.4(4) . .
C21 C22 C17 119.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 P1 2.2467(8) .
Pd1 P1 2.2467(8) 8_666
Pd1 Br1 2.4742(4) 8_666
Pd1 Br1 2.4742(4) .
P1 C17 1.802(3) .
P1 C11 1.818(3) .
P1 C2 1.835(3) .
C1 C2 1.373(4) .
C1 C9 1.435(5) .
C1 C1 1.492(6) 8_666
C2 C3 1.421(5) .
C3 C4 1.357(5) .
C4 C10 1.393(5) .
C5 C6 1.334(6) .
C5 C10 1.421(5) .
C6 C7 1.387(6) .
C7 C8 1.360(6) .
C8 C9 1.415(5) .
C9 C10 1.417(5) .
C11 C16 1.380(5) .
C11 C12 1.385(6) .
C12 C13 1.377(6) .
C13 C14 1.360(7) .
C14 C15 1.349(8) .
C15 C16 1.366(6) .
C17 C18 1.375(5) .
C17 C22 1.399(4) .
C18 C19 1.377(5) .
C19 C20 1.367(6) .
C20 C21 1.345(6) .
C21 C22 1.383(5) .
