#------------------------------------------------------------------------------
#$Date: 2018-08-21 15:35:10 +0300 (Tue, 21 Aug 2018) $
#$Revision: 210020 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/23/4302377.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_4302377
loop_
_publ_author_name
'Zhang, Yi'
'Pullarkat, Sumod A.'
'Li, Yongxin'
'Leung, Pak-Hing'
_publ_section_title
;
 Asymmetric Synthesis of Diphosphine Ligands Containing Phosphorus and
 Carbon Stereogenic Centers by Means of a Chiral Palladium Complex
 Promoted Hydrophosphination Reaction
;
_journal_coden_ASTM              INOCAJ
_journal_issue                   12
_journal_name_full               'Inorganic chemistry'
_journal_page_first              5535
_journal_page_last               5539
_journal_paper_doi               10.1021/ic900461t
_journal_volume                  48
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H42 N P2 Pd, C H2 Cl2, Cl O4'
_chemical_formula_sum            'C39 H44 Cl3 N O4 P2 Pd'
_chemical_formula_weight         865.44
_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                 92.841(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3975(5)
_cell_length_b                   9.8036(6)
_cell_length_c                   20.7827(11)
_cell_measurement_reflns_used    6669
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.71
_cell_measurement_theta_min      2.43
_cell_volume                     1912.34(19)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            37064
_diffrn_reflns_theta_full        33.39
_diffrn_reflns_theta_max         33.39
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  0.9225
_exptl_absorpt_correction_T_min  0.8275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.153
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.184
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         13784
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.0378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                12117
_reflns_number_total             13784
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4338548
_cod_data_source_file            ic900461t_si_001_1.cif
_cod_data_source_block           leung314
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4302377
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.621640(16) 0.071533(19) 0.741862(8) 0.01896(4) Uani 1 1 d . . .
C1 C 0.5410(3) 0.1465(3) 0.82508(12) 0.0209(5) Uani 1 1 d . . .
C2 C 0.5687(3) 0.1066(3) 0.89029(12) 0.0234(5) Uani 1 1 d . . .
H2 H 0.6366 0.0368 0.8997 0.028 Uiso 1 1 calc R . .
C3 C 0.5004(3) 0.1657(3) 0.93989(13) 0.0254(5) Uani 1 1 d . . .
H3 H 0.5210 0.1356 0.9828 0.031 Uiso 1 1 calc R . .
C4 C 0.3992(3) 0.2712(3) 0.92801(12) 0.0224(5) Uani 1 1 d . . .
C5 C 0.3258(3) 0.3335(4) 0.97843(14) 0.0290(6) Uani 1 1 d . . .
H5 H 0.3442 0.3036 1.0215 0.035 Uiso 1 1 calc R . .
C6 C 0.2300(3) 0.4346(3) 0.96624(15) 0.0307(6) Uani 1 1 d . . .
H6 H 0.1828 0.4755 1.0007 0.037 Uiso 1 1 calc R . .
C7 C 0.2002(3) 0.4794(3) 0.90228(14) 0.0277(6) Uani 1 1 d . . .
H7 H 0.1325 0.5500 0.8940 0.033 Uiso 1 1 calc R . .
C8 C 0.2682(3) 0.4219(3) 0.85197(13) 0.0236(5) Uani 1 1 d . . .
H8 H 0.2472 0.4533 0.8093 0.028 Uiso 1 1 calc R . .
C9 C 0.3694(3) 0.3159(3) 0.86292(12) 0.0195(4) Uani 1 1 d . . .
C10 C 0.4440(3) 0.2514(3) 0.81286(12) 0.0200(5) Uani 1 1 d . . .
C11 C 0.4243(3) 0.2997(3) 0.74415(12) 0.0225(5) Uani 1 1 d . . .
H11 H 0.3267 0.3392 0.7372 0.027 Uiso 1 1 calc R . .
C12 C 0.5350(3) 0.4098(3) 0.73089(14) 0.0281(6) Uani 1 1 d . . .
H12A H 0.6304 0.3693 0.7330 0.042 Uiso 1 1 calc R . .
H12B H 0.5306 0.4821 0.7633 0.042 Uiso 1 1 calc R . .
H12C H 0.5147 0.4485 0.6879 0.042 Uiso 1 1 calc R . .
C13 C 0.4364(3) 0.2214(4) 0.63288(13) 0.0292(6) Uani 1 1 d . . .
H13A H 0.3545 0.2811 0.6234 0.044 Uiso 1 1 calc R . .
H13B H 0.4295 0.1409 0.6050 0.044 Uiso 1 1 calc R . .
H13C H 0.5246 0.2708 0.6251 0.044 Uiso 1 1 calc R . .
C14 C 0.3105(3) 0.0892(4) 0.70837(14) 0.0283(6) Uani 1 1 d . . .
H14A H 0.2247 0.1378 0.6924 0.042 Uiso 1 1 calc R . .
H14B H 0.3017 0.0661 0.7539 0.042 Uiso 1 1 calc R . .
H14C H 0.3213 0.0053 0.6834 0.042 Uiso 1 1 calc R . .
C15 C 0.6065(3) -0.0502(3) 0.57901(13) 0.0252(5) Uani 1 1 d . . .
C16 C 0.4852(3) -0.1282(3) 0.59075(15) 0.0301(6) Uani 1 1 d . . .
H16 H 0.4769 -0.1715 0.6313 0.036 Uiso 1 1 calc R . .
C17 C 0.3773(4) -0.1420(4) 0.54293(17) 0.0381(8) Uani 1 1 d . . .
H17 H 0.2956 -0.1956 0.5505 0.046 Uiso 1 1 calc R . .
C18 C 0.3893(4) -0.0765(4) 0.48351(17) 0.0413(8) Uani 1 1 d . . .
H18 H 0.3139 -0.0824 0.4514 0.050 Uiso 1 1 calc R . .
C19 C 0.5098(4) -0.0040(4) 0.47170(15) 0.0358(7) Uani 1 1 d . . .
H19 H 0.5191 0.0368 0.4307 0.043 Uiso 1 1 calc R . .
C20 C 0.6182(3) 0.0107(3) 0.51870(14) 0.0293(6) Uani 1 1 d . . .
H20 H 0.7007 0.0622 0.5100 0.035 Uiso 1 1 calc R . .
C21 C 0.8578(3) 0.1071(3) 0.61571(13) 0.0264(6) Uani 1 1 d . . .
C22 C 0.8601(3) 0.2446(4) 0.63367(16) 0.0320(6) Uani 1 1 d . . .
H22 H 0.7924 0.2777 0.6623 0.038 Uiso 1 1 calc R . .
C23 C 0.9596(4) 0.3325(4) 0.61023(19) 0.0438(8) Uani 1 1 d . . .
H23 H 0.9593 0.4258 0.6226 0.053 Uiso 1 1 calc R . .
C24 C 1.0590(4) 0.2869(5) 0.56924(18) 0.0477(10) Uani 1 1 d . . .
H24 H 1.1281 0.3481 0.5540 0.057 Uiso 1 1 calc R . .
C25 C 1.0588(4) 0.1505(5) 0.54989(18) 0.0466(9) Uani 1 1 d . . .
H25 H 1.1263 0.1185 0.5209 0.056 Uiso 1 1 calc R . .
C26 C 0.9593(3) 0.0633(5) 0.57340(14) 0.0391(7) Uani 1 1 d . . .
H26 H 0.9596 -0.0297 0.5605 0.047 Uiso 1 1 calc R . .
C27 C 0.7469(4) -0.2877(4) 0.67939(17) 0.0373(7) Uani 1 1 d . . .
H27A H 0.8083 -0.3604 0.6975 0.056 Uiso 1 1 calc R . .
H27B H 0.7064 -0.3160 0.6371 0.056 Uiso 1 1 calc R . .
H27C H 0.6698 -0.2699 0.7083 0.056 Uiso 1 1 calc R . .
C28 C 0.8349(3) -0.1576(3) 0.67197(14) 0.0274(6) Uani 1 1 d . . .
H28 H 0.9047 -0.1744 0.6380 0.033 Uiso 1 1 calc R . .
C29 C 0.9185(3) -0.1127(3) 0.73368(14) 0.0274(6) Uani 1 1 d . . .
H29A H 0.9886 -0.0420 0.7229 0.033 Uiso 1 1 calc R . .
H29B H 0.9715 -0.1916 0.7524 0.033 Uiso 1 1 calc R . .
C30 C 0.9165(3) 0.0392(3) 0.85374(14) 0.0272(6) Uani 1 1 d . . .
H30 H 0.9471 -0.0140 0.8901 0.033 Uiso 1 1 calc R . .
C31 C 0.9641(4) 0.1665(4) 0.85199(16) 0.0351(7) Uani 1 1 d . . .
H31 H 1.0273 0.1931 0.8868 0.042 Uiso 1 1 calc R . .
C32 C 0.9318(5) 0.2707(5) 0.8034(2) 0.0611(13) Uani 1 1 d . . .
H32A H 0.8611 0.2354 0.7714 0.092 Uiso 1 1 calc R . .
H32B H 1.0190 0.2950 0.7820 0.092 Uiso 1 1 calc R . .
H32C H 0.8937 0.3519 0.8240 0.092 Uiso 1 1 calc R . .
C33 C 0.7408(3) -0.1954(3) 0.83597(13) 0.0233(5) Uani 1 1 d . . .
C34 C 0.5974(3) -0.2283(3) 0.83681(13) 0.0257(5) Uani 1 1 d . . .
H34 H 0.5280 -0.1692 0.8170 0.031 Uiso 1 1 calc R . .
C35 C 0.5550(3) -0.3476(3) 0.86655(15) 0.0301(6) Uani 1 1 d . . .
H35 H 0.4566 -0.3690 0.8676 0.036 Uiso 1 1 calc R . .
C36 C 0.6557(3) -0.4357(5) 0.89476(14) 0.0331(6) Uani 1 1 d . . .
H36 H 0.6266 -0.5183 0.9141 0.040 Uiso 1 1 calc R . .
C37 C 0.7994(4) -0.4022(4) 0.89441(17) 0.0370(8) Uani 1 1 d . . .
H37 H 0.8686 -0.4617 0.9140 0.044 Uiso 1 1 calc R . .
C38 C 0.8423(3) -0.2822(3) 0.86557(16) 0.0313(6) Uani 1 1 d . . .
H38 H 0.9405 -0.2591 0.8660 0.038 Uiso 1 1 calc R . .
C39 C 0.2633(5) 0.8960(6) 0.9376(3) 0.0693(14) Uani 1 1 d . . .
H39A H 0.3605 0.8688 0.9531 0.083 Uiso 1 1 calc R . .
H39B H 0.2562 0.9964 0.9414 0.083 Uiso 1 1 calc R . .
Cl1 Cl 0.20461(11) 0.64891(11) 0.67839(5) 0.0483(2) Uani 1 1 d . . .
Cl2 Cl 0.13911(12) 0.81975(13) 0.98650(5) 0.0557(3) Uani 1 1 d . . .
Cl3 Cl 0.23689(10) 0.84968(13) 0.85599(6) 0.0555(3) Uani 1 1 d . . .
N1 N 0.4377(2) 0.1778(3) 0.70146(10) 0.0210(4) Uani 1 1 d . . .
O1 O 0.2687(5) 0.5523(5) 0.6418(2) 0.0897(13) Uani 1 1 d . . .
O2 O 0.1059(3) 0.5886(4) 0.71982(15) 0.0577(8) Uani 1 1 d . . .
O3 O 0.1426(6) 0.7492(9) 0.6420(3) 0.204(5) Uani 1 1 d U . .
O4 O 0.3210(8) 0.7075(7) 0.7181(3) 0.150(3) Uani 1 1 d U . .
P1 P 0.72593(7) -0.00788(8) 0.64745(3) 0.02221(13) Uani 1 1 d . . .
P2 P 0.79921(7) -0.04369(8) 0.79388(3) 0.02116(13) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 80.38(9) . . ?
C1 Pd1 P2 94.06(7) . . ?
N1 Pd1 P2 173.50(6) . . ?
C1 Pd1 P1 176.88(8) . . ?
N1 Pd1 P1 101.15(6) . . ?
P2 Pd1 P1 84.57(3) . . ?
C10 C1 C2 117.7(2) . . ?
C10 C1 Pd1 112.11(18) . . ?
C2 C1 Pd1 130.2(2) . . ?
C3 C2 C1 122.1(3) . . ?
C2 C3 C4 120.8(2) . . ?
C3 C4 C5 122.1(3) . . ?
C3 C4 C9 119.0(2) . . ?
C5 C4 C9 118.9(3) . . ?
C6 C5 C4 121.3(3) . . ?
C5 C6 C7 120.1(3) . . ?
C8 C7 C6 120.6(3) . . ?
C7 C8 C9 120.8(3) . . ?
C8 C9 C10 123.8(2) . . ?
C8 C9 C4 118.2(2) . . ?
C10 C9 C4 118.0(2) . . ?
C1 C10 C9 122.3(2) . . ?
C1 C10 C11 117.0(2) . . ?
C9 C10 C11 120.6(2) . . ?
N1 C11 C10 107.5(2) . . ?
N1 C11 C12 112.2(2) . . ?
C10 C11 C12 109.8(2) . . ?
C20 C15 C16 119.3(3) . . ?
C20 C15 P1 122.2(2) . . ?
C16 C15 P1 117.6(2) . . ?
C17 C16 C15 119.9(3) . . ?
C16 C17 C18 119.8(3) . . ?
C19 C18 C17 119.9(3) . . ?
C18 C19 C20 120.9(3) . . ?
C19 C20 C15 120.1(3) . . ?
C26 C21 C22 117.6(3) . . ?
C26 C21 P1 122.4(3) . . ?
C22 C21 P1 120.1(2) . . ?
C23 C22 C21 120.7(3) . . ?
C24 C23 C22 120.7(4) . . ?
C23 C24 C25 120.0(3) . . ?
C26 C25 C24 119.0(4) . . ?
C25 C26 C21 122.0(4) . . ?
C27 C28 C29 114.3(3) . . ?
C27 C28 P1 113.2(2) . . ?
C29 C28 P1 104.8(2) . . ?
C28 C29 P2 111.63(19) . . ?
C31 C30 P2 126.7(2) . . ?
C30 C31 C32 128.3(3) . . ?
C34 C33 C38 119.7(3) . . ?
C34 C33 P2 120.8(2) . . ?
C38 C33 P2 119.5(2) . . ?
C33 C34 C35 120.1(3) . . ?
C36 C35 C34 120.4(3) . . ?
C35 C36 C37 119.5(3) . . ?
C38 C37 C36 120.3(3) . . ?
C37 C38 C33 120.0(3) . . ?
Cl2 C39 Cl3 112.5(3) . . ?
O3 Cl1 O1 112.3(4) . . ?
O3 Cl1 O2 111.4(2) . . ?
O1 Cl1 O2 111.4(3) . . ?
O3 Cl1 O4 108.7(6) . . ?
O1 Cl1 O4 104.4(4) . . ?
O2 Cl1 O4 108.4(3) . . ?
C13 N1 C14 107.0(2) . . ?
C13 N1 C11 110.0(2) . . ?
C14 N1 C11 108.5(2) . . ?
C13 N1 Pd1 118.72(16) . . ?
C14 N1 Pd1 108.20(18) . . ?
C11 N1 Pd1 104.14(15) . . ?
C15 P1 C21 105.23(13) . . ?
C15 P1 C28 110.31(14) . . ?
C21 P1 C28 102.34(14) . . ?
C15 P1 Pd1 117.34(9) . . ?
C21 P1 Pd1 114.40(10) . . ?
C28 P1 Pd1 106.22(9) . . ?
C30 P2 C33 102.92(13) . . ?
C30 P2 C29 105.06(14) . . ?
C33 P2 C29 103.49(14) . . ?
C30 P2 Pd1 121.10(10) . . ?
C33 P2 Pd1 114.00(9) . . ?
C29 P2 Pd1 108.59(10) . . ?
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 2.058(3) . ?
Pd1 N1 2.153(2) . ?
Pd1 P2 2.2473(7) . ?
Pd1 P1 2.3680(7) . ?
C1 C10 1.389(4) . ?
C1 C2 1.422(4) . ?
C2 C3 1.369(4) . ?
C3 C4 1.418(4) . ?
C4 C5 1.421(4) . ?
C4 C9 1.436(4) . ?
C5 C6 1.354(5) . ?
C6 C7 1.415(4) . ?
C7 C8 1.373(4) . ?
C8 C9 1.419(4) . ?
C9 C10 1.430(3) . ?
C10 C11 1.507(4) . ?
C11 N1 1.497(4) . ?
C11 C12 1.533(4) . ?
C13 N1 1.487(3) . ?
C14 N1 1.491(4) . ?
C15 C20 1.397(4) . ?
C15 C16 1.404(4) . ?
C15 P1 1.815(3) . ?
C16 C17 1.391(5) . ?
C17 C18 1.401(5) . ?
C18 C19 1.370(5) . ?
C19 C20 1.383(4) . ?
C21 C26 1.397(4) . ?
C21 C22 1.398(5) . ?
C21 P1 1.823(3) . ?
C22 C23 1.379(5) . ?
C23 C24 1.370(6) . ?
C24 C25 1.397(7) . ?
C25 C26 1.374(5) . ?
C27 C28 1.532(5) . ?
C28 C29 1.535(4) . ?
C28 P1 1.847(3) . ?
C29 P2 1.849(3) . ?
C30 C31 1.327(5) . ?
C30 P2 1.813(3) . ?
C31 C32 1.459(6) . ?
C33 C34 1.387(4) . ?
C33 C38 1.398(4) . ?
C33 P2 1.823(3) . ?
C34 C35 1.391(4) . ?
C35 C36 1.390(5) . ?
C36 C37 1.390(4) . ?
C37 C38 1.390(5) . ?
C39 Cl2 1.753(5) . ?
C39 Cl3 1.761(6) . ?
Cl1 O3 1.355(4) . ?
Cl1 O1 1.373(4) . ?
Cl1 O2 1.425(3) . ?
Cl1 O4 1.455(6) . ?
