#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:40:15 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179198 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/36/4313649.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_4313649
loop_
_publ_author_name
'Yongxin Li'
'S. Selvaratnam'
'Jagadese J. Vittal'
'Pak-Hing Leung'
_publ_contact_author
;
      Professor Pak-Hing Leung
      Department of Chemistry
      National University of Singapore
      SINGAPORE 117543
;
_publ_contact_author_email       chmlph@nus.edu.sg
_publ_contact_author_fax         '(65) 6779 1691'
_publ_contact_author_phone       '(65) 6874 2682'
_publ_section_title
;
 A Rational Approach to the Design and Synthesis of Chiral
 Organopalladium-Amine Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3229
_journal_page_last               3236
_journal_paper_doi               10.1021/ic030018l
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C24 H31 Cl N P Pd'
_chemical_formula_weight         506.32
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8274(1)
_cell_length_b                   12.5733(2)
_cell_length_c                   21.7013(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2408.62(5)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'ω 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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15522
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   'Sadabs (sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       0.0099(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.070
_refine_ls_goodness_of_fit_obs   1.073
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_restrained_S_obs      1.073
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_obs          0.0219
_refine_ls_shift/esd_max         0.004
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0276P)²+0.4099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0572
_refine_ls_wR_factor_obs         0.0556
_reflns_number_observed          5491
_reflns_number_total             5834
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic030018l_5.cif
_cod_data_source_block           compd(S)-9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0276P)^2^+0.4099P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0276P)^2^+0.4099P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4313649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Pd1 Pd 0.38514(2) 0.334996(13) 0.201902(7) 0.03555(5) Uani 1 d . .
Cl1 Cl 0.59799(8) 0.35624(6) 0.13374(3) 0.0598(2) Uani 1 d . .
P1 P 0.22676(6) 0.33550(6) 0.12141(2) 0.03758(12) Uani 1 d . .
N1 N 0.5120(2) 0.2698(2) 0.27879(9) 0.0411(4) Uani 1 d . .
C1 C 0.2195(2) 0.3230(2) 0.26501(10) 0.0386(5) Uani 1 d . .
C2 C 0.0924(3) 0.3888(2) 0.27352(11) 0.0442(5) Uani 1 d . .
C3 C -0.0055(3) 0.3641(3) 0.32245(13) 0.0556(7) Uani 1 d . .
H3A H -0.0906(3) 0.4064(3) 0.32883(13) 0.067 Uiso 1 calc R .
C4 C 0.0200(3) 0.2796(3) 0.36124(13) 0.0607(8) Uani 1 d . .
H4A H -0.0505(3) 0.2637(3) 0.39175(13) 0.073 Uiso 1 calc R .
C5 C 0.1498(3) 0.2171(2) 0.35558(12) 0.0523(6) Uani 1 d . .
C6 C 0.2504(3) 0.2416(2) 0.30760(10) 0.0408(5) Uani 1 d . .
C7 C 0.0620(3) 0.4866(2) 0.23505(14) 0.0578(7) Uani 1 d . .
H7A H 0.1381(3) 0.4928(2) 0.20365(14) 0.087 Uiso 1 calc R .
H7B H 0.0646(3) 0.5486(2) 0.26091(14) 0.087 Uiso 1 calc R .
H7C H -0.0360(3) 0.4808(2) 0.21615(14) 0.087 Uiso 1 calc R .
C8 C 0.1772(4) 0.1270(3) 0.40031(14) 0.0756(10) Uani 1 d . .
H8A H 0.2707(4) 0.0921(3) 0.39022(14) 0.113 Uiso 1 calc R .
H8B H 0.0954(4) 0.0769(3) 0.39766(14) 0.113 Uiso 1 calc R .
H8C H 0.1829(4) 0.1547(3) 0.44146(14) 0.113 Uiso 1 calc R .
C9 C 0.4007(3) 0.1862(2) 0.30067(11) 0.0458(5) Uani 1 d . .
H9A H 0.4332(3) 0.1609(2) 0.34130(11) 0.055 Uiso 1 calc R .
C10 C 0.3915(4) 0.0910(2) 0.25718(14) 0.0628(7) Uani 1 d . .
H10A H 0.4893(4) 0.0581(2) 0.25406(14) 0.094 Uiso 1 calc R .
H10B H 0.3595(4) 0.1145(2) 0.21716(14) 0.094 Uiso 1 calc R .
H10C H 0.3197(4) 0.0405(2) 0.27298(14) 0.094 Uiso 1 calc R .
C11 C 0.5386(3) 0.3473(2) 0.32908(11) 0.0532(6) Uani 1 d . .
H11A H 0.4441(3) 0.3790(2) 0.34099(11) 0.080 Uiso 1 calc R .
H11B H 0.6067(3) 0.4017(2) 0.31499(11) 0.080 Uiso 1 calc R .
H11C H 0.5824(3) 0.3114(2) 0.36384(11) 0.080 Uiso 1 calc R .
C12 C 0.6606(3) 0.2230(3) 0.26199(15) 0.0614(7) Uani 1 d . .
H12A H 0.6469(3) 0.1723(3) 0.22940(15) 0.092 Uiso 1 calc R .
H12B H 0.7034(3) 0.1881(3) 0.29728(15) 0.092 Uiso 1 calc R .
H12C H 0.7277(3) 0.2783(3) 0.24843(15) 0.092 Uiso 1 calc R .
C13 C 0.2796(3) 0.2250(2) 0.07325(11) 0.0445(5) Uani 1 d . .
H13A H 0.3743(3) 0.2162(2) 0.05515(11) 0.053 Uiso 1 calc R .
C14 C 0.1634(3) 0.1569(2) 0.06710(10) 0.0461(5) Uani 1 d . .
C15 C 0.0230(3) 0.1926(2) 0.09838(10) 0.0445(5) Uani 1 d . .
C16 C 0.0367(3) 0.2859(2) 0.12810(11) 0.0439(5) Uani 1 d . .
H16A H -0.0412(3) 0.3199(2) 0.14915(11) 0.053 Uiso 1 calc R .
C17 C -0.1211(3) 0.1288(3) 0.09589(14) 0.0644(7) Uani 1 d . .
H17A H -0.1045(3) 0.0653(3) 0.07226(14) 0.097 Uiso 1 calc R .
H17B H -0.1993(3) 0.1704(3) 0.07686(14) 0.097 Uiso 1 calc R .
H17C H -0.1514(3) 0.1100(3) 0.13695(14) 0.097 Uiso 1 calc R .
C18 C 0.1691(4) 0.0550(2) 0.03085(15) 0.0659(8) Uani 1 d . .
H18A H 0.0726(4) 0.0200(2) 0.03321(15) 0.099 Uiso 1 calc R .
H18B H 0.2460(4) 0.0095(2) 0.04762(15) 0.099 Uiso 1 calc R .
H18C H 0.1922(4) 0.0706(2) -0.01143(15) 0.099 Uiso 1 calc R .
C19 C 0.2137(3) 0.4503(2) 0.06968(10) 0.0416(5) Uani 1 d . .
C20 C 0.3138(4) 0.5342(2) 0.07443(13) 0.0598(7) Uani 1 d . .
H20A H 0.3851(4) 0.5355(2) 0.10595(13) 0.072 Uiso 1 calc R .
C21 C 0.3077(4) 0.6166(3) 0.0321(2) 0.0734(9) Uani 1 d . .
H21A H 0.3747(4) 0.6733(3) 0.0357(2) 0.088 Uiso 1 calc R .
C22 C 0.2033(4) 0.6155(3) -0.0152(2) 0.0746(10) Uani 1 d . .
H22A H 0.2009(4) 0.6705(3) -0.0438(2) 0.090 Uiso 1 calc R .
C23 C 0.1034(4) 0.5328(3) -0.01955(13) 0.0670(8) Uani 1 d . .
H23A H 0.0315(4) 0.5323(3) -0.05090(13) 0.080 Uiso 1 calc R .
C24 C 0.1083(3) 0.4504(2) 0.02217(11) 0.0534(6) Uani 1 d . .
H24A H 0.0404(3) 0.3942(2) 0.01850(11) 0.064 Uiso 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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C1 Pd1 N1 79.80(9) . . ?
C1 Pd1 P1 94.45(6) . . ?
N1 Pd1 P1 157.47(6) . . ?
C1 Pd1 Cl1 174.70(6) . . ?
N1 Pd1 Cl1 96.42(6) . . ?
P1 Pd1 Cl1 90.44(2) . . ?
C16 P1 C13 91.20(12) . . ?
C16 P1 C19 105.33(11) . . ?
C13 P1 C19 105.58(11) . . ?
C16 P1 Pd1 121.31(8) . . ?
C13 P1 Pd1 106.80(8) . . ?
C19 P1 Pd1 121.33(9) . . ?
C11 N1 C12 107.5(2) . . ?
C11 N1 C9 109.2(2) . . ?
C12 N1 C9 112.1(2) . . ?
C11 N1 Pd1 113.6(2) . . ?
C12 N1 Pd1 114.7(2) . . ?
C9 N1 Pd1 99.72(13) . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 Pd1 111.2(2) . . ?
C2 C1 Pd1 128.7(2) . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 C7 119.2(2) . . ?
C1 C2 C7 123.3(2) . . ?
C4 C3 C2 122.2(3) . . ?
C3 C4 C5 121.1(3) . . ?
C4 C5 C6 117.5(3) . . ?
C4 C5 C8 119.8(3) . . ?
C6 C5 C8 122.7(3) . . ?
C5 C6 C1 121.7(2) . . ?
C5 C6 C9 122.0(2) . . ?
C1 C6 C9 116.2(2) . . ?
C6 C9 N1 106.4(2) . . ?
C6 C9 C10 112.1(2) . . ?
N1 C9 C10 112.6(2) . . ?
C14 C13 P1 110.6(2) . . ?
C13 C14 C15 113.6(2) . . ?
C13 C14 C18 124.7(2) . . ?
C15 C14 C18 121.6(2) . . ?
C16 C15 C14 114.1(2) . . ?
C16 C15 C17 123.9(2) . . ?
C14 C15 C17 122.0(2) . . ?
C15 C16 P1 110.4(2) . . ?
C20 C19 C24 118.9(2) . . ?
C20 C19 P1 121.1(2) . . ?
C24 C19 P1 119.8(2) . . ?
C19 C20 C21 119.8(3) . . ?
C22 C21 C20 120.8(3) . . ?
C23 C22 C21 119.3(3) . . ?
C22 C23 C24 120.5(3) . . ?
C23 C24 C19 120.7(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 C1 2.009(2) . ?
Pd1 N1 2.170(2) . ?
Pd1 P1 2.2373(5) . ?
Pd1 Cl1 2.4062(6) . ?
P1 C16 1.796(3) . ?
P1 C13 1.800(3) . ?
P1 C19 1.832(2) . ?
N1 C11 1.482(3) . ?
N1 C12 1.484(3) . ?
N1 C9 1.514(3) . ?
C1 C6 1.405(3) . ?
C1 C2 1.406(3) . ?
C2 C3 1.404(4) . ?
C2 C7 1.511(4) . ?
C3 C4 1.374(4) . ?
C4 C5 1.395(4) . ?
C5 C6 1.402(3) . ?
C5 C8 1.512(4) . ?
C6 C9 1.506(3) . ?
C9 C10 1.527(3) . ?
C13 C14 1.342(4) . ?
C14 C15 1.483(3) . ?
C14 C18 1.504(4) . ?
C15 C16 1.344(4) . ?
C15 C17 1.505(4) . ?
C19 C20 1.380(4) . ?
C19 C24 1.389(4) . ?
C20 C21 1.385(4) . ?
C21 C22 1.380(5) . ?
C22 C23 1.367(5) . ?
C23 C24 1.377(4) . ?
