#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:14:00 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178554 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/62/4066217.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_4066217
loop_
_publ_author_name
'Chen, Shuli'
'Ng, Joseph Kok-Peng'
'Pullarkat, Sumod A.'
'Liu, Fengli'
'Li, Yongxin'
'Leung, Pak-Hing'
_publ_section_title
;
 Asymmetric Synthesis of New Diphosphines and Pyridylphosphines via a
 Kinetic Resolution Process Promoted and Controlled by a Chiral
 Palladacycle
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              3374
_journal_paper_doi               10.1021/om100358g
_journal_volume                  29
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H26 Cl2 P2 Pd'
_chemical_formula_sum            'C23 H26 Cl2 P2 Pd'
_chemical_formula_weight         541.68
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.444(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9434(3)
_cell_length_b                   13.0220(4)
_cell_length_c                   10.8172(4)
_cell_measurement_reflns_used    6079
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      29.84
_cell_measurement_theta_min      2.46
_cell_volume                     1164.36(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13429
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    1.171
_exptl_absorpt_correction_T_max  0.9547
_exptl_absorpt_correction_T_min  0.7202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.648
_refine_diff_density_min         -2.037
_refine_diff_density_rms         0.193
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5630
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0772P)²+3.7815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1549
_reflns_number_gt                5165
_reflns_number_total             5630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100358g_si_001.cif
_cod_data_source_block           leung290
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

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 'not measured' 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_original_sg_symbol_H-M      P2(1)
_cod_database_code               4066217
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Pd1 Pd 0.93745(5) 0.16882(4) 0.20566(4) 0.02078(11) Uani 1 1 d .
C1 C 1.1826(7) 0.1550(7) 0.5510(6) 0.0292(15) Uani 1 1 d .
C2 C 1.2619(8) 0.1993(7) 0.6764(7) 0.0381(18) Uani 1 1 d .
H2 H 1.2294 0.2640 0.6958 0.046 Uiso 1 1 calc R
C3 C 1.3898(9) 0.1473(9) 0.7732(8) 0.047(2) Uani 1 1 d .
H3 H 1.4441 0.1778 0.8573 0.056 Uiso 1 1 calc R
C4 C 1.4376(10) 0.0520(9) 0.7471(9) 0.049(2) Uani 1 1 d .
H4 H 1.5225 0.0174 0.8141 0.059 Uiso 1 1 calc R
C5 C 1.3612(10) 0.0064(7) 0.6223(9) 0.045(2) Uani 1 1 d .
H5 H 1.3949 -0.0581 0.6035 0.054 Uiso 1 1 calc R
C6 C 1.2316(9) 0.0593(7) 0.5247(7) 0.0338(15) Uani 1 1 d .
H6 H 1.1777 0.0290 0.4405 0.041 Uiso 1 1 calc R
C7 C 0.8506(8) 0.2342(5) 0.4677(6) 0.0229(11) Uani 1 1 d .
C8 C 0.8654(8) 0.2735(7) 0.5926(7) 0.0317(14) Uani 1 1 d .
H8 H 0.9654 0.2996 0.6511 0.038 Uiso 1 1 calc R
C9 C 0.7333(11) 0.2740(7) 0.6305(8) 0.0406(18) Uani 1 1 d .
H9 H 0.7457 0.2968 0.7163 0.049 Uiso 1 1 calc R
C10 C 0.5843(11) 0.2414(7) 0.5426(10) 0.044(2) Uani 1 1 d .
H10 H 0.4949 0.2440 0.5680 0.053 Uiso 1 1 calc R
C11 C 0.5646(9) 0.2047(8) 0.4171(10) 0.045(2) Uani 1 1 d .
H11 H 0.4628 0.1818 0.3578 0.054 Uiso 1 1 calc R
C12 C 0.6978(8) 0.2020(7) 0.3796(8) 0.0361(16) Uani 1 1 d .
H12 H 0.6846 0.1783 0.2940 0.043 Uiso 1 1 calc R
C13 C 1.1071(9) 0.3537(6) 0.4292(7) 0.0291(14) Uani 1 1 d .
H13A H 1.1027 0.3891 0.5077 0.035 Uiso 1 1 calc R
H13B H 1.2205 0.3498 0.4390 0.035 Uiso 1 1 calc R
C14 C 1.0095(9) 0.4138(6) 0.3026(7) 0.0282(13) Uani 1 1 d .
H14 H 0.9006 0.4247 0.3039 0.034 Uiso 1 1 calc R
C15 C 1.0783(13) 0.5199(7) 0.2957(9) 0.045(2) Uani 1 1 d .
H15A H 1.0642 0.5642 0.3625 0.068 Uiso 1 1 calc R
H15B H 1.0218 0.5489 0.2075 0.068 Uiso 1 1 calc R
H15C H 1.1926 0.5139 0.3127 0.068 Uiso 1 1 calc R
C16 C 1.1681(8) 0.3442(7) 0.1254(7) 0.0316(14) Uani 1 1 d .
H16A H 1.1750 0.4156 0.0995 0.038 Uiso 1 1 calc R
H16B H 1.2605 0.3317 0.2093 0.038 Uiso 1 1 calc R
C17 C 1.1839(13) 0.2747(9) 0.0190(10) 0.053(2) Uani 1 1 d .
H17A H 1.1782 0.2036 0.0435 0.080 Uiso 1 1 calc R
H17B H 1.2869 0.2872 0.0113 0.080 Uiso 1 1 calc R
H17C H 1.0966 0.2889 -0.0661 0.080 Uiso 1 1 calc R
C18 C 0.8179(8) 0.3887(6) 0.0216(7) 0.0269(13) Uani 1 1 d .
C19 C 0.8416(9) 0.4475(6) -0.0757(8) 0.0340(15) Uani 1 1 d .
H19 H 0.9462 0.4570 -0.0748 0.041 Uiso 1 1 calc R
C20 C 0.7079(10) 0.4925(7) -0.1756(9) 0.0426(19) Uani 1 1 d .
H20 H 0.7234 0.5320 -0.2424 0.051 Uiso 1 1 calc R
C21 C 0.5552(11) 0.4801(8) -0.1779(10) 0.046(2) Uani 1 1 d .
H21 H 0.4672 0.5123 -0.2448 0.055 Uiso 1 1 calc R
C22 C 0.5296(11) 0.4199(8) -0.0812(10) 0.051(2) Uani 1 1 d .
H22 H 0.4245 0.4091 -0.0838 0.062 Uiso 1 1 calc R
C23 C 0.6615(10) 0.3764(7) 0.0184(9) 0.0408(18) Uani 1 1 d .
H23 H 0.6457 0.3376 0.0856 0.049 Uiso 1 1 calc R
Cl1 Cl 0.8834(2) -0.00057(14) 0.26040(18) 0.0326(3) Uani 1 1 d .
Cl2 Cl 0.8287(2) 0.13184(16) -0.02351(16) 0.0376(4) Uani 1 1 d .
P1 P 1.02352(19) 0.22318(13) 0.41887(15) 0.0209(3) Uani 1 1 d .
P2 P 0.9827(2) 0.32924(13) 0.15660(16) 0.0219(3) Uani 1 1 d .
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'
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
P2 Pd1 P1 85.81(6)
P2 Pd1 Cl2 88.88(7)
P1 Pd1 Cl2 172.63(7)
P2 Pd1 Cl1 178.33(7)
P1 Pd1 Cl1 93.39(6)
Cl2 Pd1 Cl1 91.78(7)
C6 C1 C2 119.3(7)
C6 C1 P1 119.5(5)
C2 C1 P1 121.2(6)
C1 C2 C3 119.7(8)
C4 C3 C2 120.9(8)
C3 C4 C5 120.5(8)
C4 C5 C6 118.4(9)
C1 C6 C5 121.2(7)
C12 C7 C8 118.3(6)
C12 C7 P1 119.7(5)
C8 C7 P1 122.0(5)
C9 C8 C7 120.4(7)
C10 C9 C8 120.2(7)
C9 C10 C11 120.7(7)
C10 C11 C12 119.3(8)
C11 C12 C7 120.9(7)
C14 C13 P1 109.8(5)
C15 C14 C13 113.9(6)
C15 C14 P2 114.7(5)
C13 C14 P2 107.5(5)
C17 C16 P2 115.6(6)
C19 C18 C23 119.3(7)
C19 C18 P2 122.5(5)
C23 C18 P2 118.2(5)
C18 C19 C20 119.1(7)
C21 C20 C19 121.3(7)
C20 C21 C22 120.1(8)
C23 C22 C21 118.7(8)
C22 C23 C18 121.5(7)
C1 P1 C7 107.9(3)
C1 P1 C13 103.0(4)
C7 P1 C13 106.2(3)
C1 P1 Pd1 120.8(2)
C7 P1 Pd1 109.1(2)
C13 P1 Pd1 108.9(2)
C18 P2 C16 108.9(3)
C18 P2 C14 103.5(3)
C16 P2 C14 105.2(3)
C18 P2 Pd1 115.3(2)
C16 P2 Pd1 113.9(3)
C14 P2 Pd1 109.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 P2 2.2302(17)
Pd1 P1 2.2488(15)
Pd1 Cl2 2.3413(16)
Pd1 Cl1 2.3809(19)
C1 C6 1.386(12)
C1 C2 1.394(9)
C1 P1 1.818(7)
C2 C3 1.396(11)
C3 C4 1.377(16)
C4 C5 1.392(14)
C5 C6 1.413(10)
C7 C12 1.399(9)
C7 C8 1.403(9)
C7 P1 1.821(6)
C8 C9 1.391(10)
C9 C10 1.376(13)
C10 C11 1.386(13)
C11 C12 1.397(10)
C13 C14 1.529(10)
C13 P1 1.843(7)
C14 C15 1.525(11)
C14 P2 1.864(7)
C16 C17 1.512(12)
C16 P2 1.824(7)
C18 C19 1.382(9)
C18 C23 1.395(10)
C18 P2 1.806(7)
C19 C20 1.398(11)
C20 C21 1.366(12)
C21 C22 1.395(13)
C22 C23 1.379(12)
