#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:30:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178624 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/35/4073563.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_4073563
loop_
_publ_author_name
'Grushin, Vladimir V.'
'Marshall, William J.'
_publ_section_title
;
 Ar−F Reductive Elimination from Palladium(II) Revisited†
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              4997
_journal_paper_doi               10.1021/om700469k
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C58 H62 Cl4 F2 P2 Pd2'
_chemical_formula_weight         1213.62
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 124.594(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.772(9)
_cell_length_b                   13.907(4)
_cell_length_c                   17.997(6)
_cell_measurement_temperature    293(2)
_cell_volume                     6134(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker 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  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35173
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ireg.blok
_exptl_crystal_F_000             2472
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.240
_refine_diff_density_max         1.446
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         7113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0524
_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)+(0.0884P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                4570
_reflns_number_total             7113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om700469k-file004.cif
_cod_data_source_block           07043
_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 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4073563
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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 0.056545(11) 0.51562(2) 0.25705(2) 0.04160(14) Uani 1 1 d .
P1 P 0.11612(4) 0.40777(9) 0.27051(8) 0.0475(3) Uani 1 1 d .
F1 F 0.0000 0.6106(3) 0.2500 0.0557(9) Uani 1 2 d S
C1 C 0.09717(15) 0.6254(3) 0.2517(3) 0.0412(9) Uani 1 1 d .
Cl1 Cl 0.20354(12) 0.09511(19) 0.1684(2) 0.1575(10) Uani 1 1 d .
F2 F 0.0000 0.4165(2) 0.2500 0.0416(7) Uani 1 2 d S
C2 C 0.11146(17) 0.7006(3) 0.3118(3) 0.0522(11) Uani 1 1 d .
H2A H 0.1073 0.6933 0.3590 0.063 Uiso 1 1 calc R
Cl2 Cl 0.20958(10) 0.23180(17) 0.05231(18) 0.1353(8) Uani 1 1 d .
C3 C 0.13173(19) 0.7863(4) 0.3033(3) 0.0575(12) Uani 1 1 d .
H3A H 0.1408 0.8353 0.3447 0.069 Uiso 1 1 calc R
C4 C 0.13882(19) 0.8005(4) 0.2344(3) 0.0600(12) Uani 1 1 d .
C5 C 0.12402(19) 0.7260(4) 0.1743(3) 0.0590(12) Uani 1 1 d .
H5A H 0.1283 0.7333 0.1273 0.071 Uiso 1 1 calc R
C6 C 0.10311(16) 0.6409(3) 0.1817(3) 0.0497(11) Uani 1 1 d .
H6A H 0.0928 0.5930 0.1388 0.060 Uiso 1 1 calc R
C7 C 0.1623(3) 0.8936(4) 0.2269(4) 0.0843(18) Uani 1 1 d .
H7A H 0.1905 0.8795 0.2179 0.126 Uiso 1 1 calc R
H7B H 0.1774 0.9302 0.2813 0.126 Uiso 1 1 calc R
H7C H 0.1340 0.9301 0.1765 0.126 Uiso 1 1 calc R
C8 C 0.18708(15) 0.4211(3) 0.3690(3) 0.0483(10) Uani 1 1 d .
C9 C 0.19789(17) 0.5009(3) 0.4231(3) 0.0528(12) Uani 1 1 d .
H9A H 0.1702 0.5452 0.4056 0.063 Uiso 1 1 calc R
C10 C 0.24839(19) 0.5165(4) 0.5018(4) 0.0631(13) Uani 1 1 d .
H10A H 0.2549 0.5704 0.5371 0.076 Uiso 1 1 calc R
C11 C 0.28922(18) 0.4499(5) 0.5271(4) 0.0721(15) Uani 1 1 d .
H11A H 0.3235 0.4585 0.5805 0.087 Uiso 1 1 calc R
C12 C 0.27954(18) 0.3719(4) 0.4742(4) 0.0708(15) Uani 1 1 d .
H12A H 0.3078 0.3287 0.4921 0.085 Uiso 1 1 calc R
C13 C 0.22838(17) 0.3546(4) 0.3935(3) 0.0594(12) Uani 1 1 d .
C14 C 0.2220(2) 0.2639(4) 0.3416(4) 0.0727(15) Uani 1 1 d .
H14A H 0.2574 0.2397 0.3617 0.109 Uiso 1 1 calc R
H14B H 0.2019 0.2783 0.2783 0.109 Uiso 1 1 calc R
H14C H 0.2028 0.2163 0.3518 0.109 Uiso 1 1 calc R
C15 C 0.11632(18) 0.4084(3) 0.1701(3) 0.0580(12) Uani 1 1 d .
C16 C 0.1641(2) 0.4354(4) 0.1764(4) 0.0663(14) Uani 1 1 d .
H16A H 0.1964 0.4445 0.2330 0.080 Uiso 1 1 calc R
C17 C 0.1639(3) 0.4484(5) 0.1010(5) 0.0851(18) Uani 1 1 d .
H17A H 0.1955 0.4672 0.1060 0.102 Uiso 1 1 calc R
C18 C 0.1160(3) 0.4334(5) 0.0171(4) 0.096(2) Uani 1 1 d .
H18A H 0.1157 0.4411 -0.0345 0.115 Uiso 1 1 calc R
C19 C 0.0695(3) 0.4075(5) 0.0089(4) 0.093(2) Uani 1 1 d .
H19A H 0.0380 0.3977 -0.0484 0.112 Uiso 1 1 calc R
C20 C 0.0677(2) 0.3955(4) 0.0831(4) 0.0723(16) Uani 1 1 d .
C21 C 0.01385(18) 0.3728(4) 0.0697(4) 0.0753(17) Uani 1 1 d .
H21A H -0.0085 0.4295 0.0498 0.113 Uiso 1 1 calc R
H21B H 0.0204 0.3512 0.1258 0.113 Uiso 1 1 calc R
H21C H -0.0045 0.3231 0.0251 0.113 Uiso 1 1 calc R
C22 C 0.09782(17) 0.2851(4) 0.2810(4) 0.0693(16) Uani 1 1 d .
C23 C 0.08869(19) 0.2147(4) 0.2179(4) 0.0829(19) Uani 1 1 d .
H23A H 0.0931 0.2302 0.1722 0.099 Uiso 1 1 calc R
C24 C 0.0734(3) 0.1238(6) 0.2231(8) 0.143(5) Uani 1 1 d .
H24A H 0.0665 0.0784 0.1799 0.171 Uiso 1 1 calc R
C25 C 0.0681(3) 0.0990(7) 0.2920(9) 0.152(6) Uani 1 1 d .
H25A H 0.0589 0.0362 0.2959 0.182 Uiso 1 1 calc R
C26 C 0.0765(2) 0.1666(5) 0.3559(6) 0.112(3) Uani 1 1 d .
H26A H 0.1041 0.1413 0.4151 0.135 Uiso 1 1 calc R
H26B H 0.0429 0.1716 0.3527 0.135 Uiso 1 1 calc R
C27 C 0.09243(18) 0.2614(4) 0.3502(4) 0.0734(17) Uani 1 1 d .
C28 C 0.10338(19) 0.3312(5) 0.4220(4) 0.0813(19) Uani 1 1 d .
H28A H 0.0798 0.3859 0.3946 0.122 Uiso 1 1 calc R
H28B H 0.1407 0.3517 0.4549 0.122 Uiso 1 1 calc R
H28C H 0.0966 0.3006 0.4626 0.122 Uiso 1 1 calc R
C29 C 0.2395(3) 0.1683(7) 0.1487(5) 0.132(3) Uani 1 1 d .
H29A H 0.2681 0.1301 0.1528 0.158 Uiso 1 1 calc R
H29B H 0.2573 0.2141 0.1980 0.158 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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
C1 Pd1 F1 90.19(14) . .
C1 Pd1 F2 168.92(13) . .
F1 Pd1 F2 79.75(10) . .
C1 Pd1 P1 93.06(12) . .
F1 Pd1 P1 176.10(7) . .
F2 Pd1 P1 97.17(8) . .
C1 Pd1 Pd1 129.31(11) . 2
F1 Pd1 Pd1 39.27(8) . 2
F2 Pd1 Pd1 40.48(6) . 2
P1 Pd1 Pd1 137.60(3) . 2
C15 P1 C22 106.1(3) . .
C15 P1 C8 107.9(2) . .
C22 P1 C8 103.9(2) . .
C15 P1 Pd1 109.99(14) . .
C22 P1 Pd1 111.88(17) . .
C8 P1 Pd1 116.39(15) . .
Pd1 F1 Pd1 101.46(15) 2 .
C6 C1 C2 116.8(4) . .
C6 C1 Pd1 124.1(3) . .
C2 C1 Pd1 117.9(3) . .
Pd1 F2 Pd1 99.05(13) 2 .
C3 C2 C1 121.5(4) . .
C2 C3 C4 121.4(4) . .
C5 C4 C3 116.9(4) . .
C5 C4 C7 122.1(5) . .
C3 C4 C7 121.0(5) . .
C4 C5 C6 122.1(4) . .
C5 C6 C1 121.3(4) . .
C9 C8 C13 119.8(4) . .
C9 C8 P1 116.0(3) . .
C13 C8 P1 124.2(4) . .
C10 C9 C8 122.0(4) . .
C9 C10 C11 118.4(5) . .
C12 C11 C10 120.3(5) . .
C11 C12 C13 122.3(5) . .
C8 C13 C12 117.2(5) . .
C8 C13 C14 125.3(4) . .
C12 C13 C14 117.5(4) . .
C16 C15 C20 118.1(5) . .
C16 C15 P1 119.7(4) . .
C20 C15 P1 121.6(4) . .
C17 C16 C15 121.3(5) . .
C16 C17 C18 119.0(6) . .
C19 C18 C17 121.0(7) . .
C18 C19 C20 121.8(6) . .
C19 C20 C15 118.7(6) . .
C19 C20 C21 119.5(5) . .
C15 C20 C21 121.8(5) . .
C27 C22 C23 119.6(6) . .
C27 C22 P1 120.6(5) . .
C23 C22 P1 119.8(5) . .
C24 C23 C22 120.7(8) . .
C23 C24 C25 120.4(10) . .
C24 C25 C26 121.0(9) . .
C25 C26 C27 118.4(9) . .
C22 C27 C26 120.0(7) . .
C22 C27 C28 122.9(5) . .
C26 C27 C28 117.1(7) . .
Cl1 C29 Cl2 121.1(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 1.984(4) .
Pd1 F1 2.086(2) .
Pd1 F2 2.123(2) .
Pd1 P1 2.2286(12) .
Pd1 Pd1 3.2295(12) 2
P1 C15 1.810(5) .
P1 C22 1.833(6) .
P1 C8 1.840(4) .
F1 Pd1 2.086(2) 2
C1 C6 1.385(6) .
C1 C2 1.387(6) .
Cl1 C29 1.654(8) .
F2 Pd1 2.123(2) 2
C2 C3 1.382(6) .
Cl2 C29 1.681(8) .
C3 C4 1.385(7) .
C4 C5 1.377(7) .
C4 C7 1.514(7) .
C5 C6 1.378(6) .
C8 C9 1.388(6) .
C8 C13 1.395(6) .
C9 C10 1.377(6) .
C10 C11 1.383(7) .
C11 C12 1.361(8) .
C12 C13 1.406(7) .
C13 C14 1.517(7) .
C15 C16 1.414(7) .
C15 C20 1.416(7) .
C16 C17 1.365(8) .
C17 C18 1.383(9) .
C18 C19 1.355(10) .
C19 C20 1.376(9) .
C20 C21 1.514(8) .
C22 C27 1.382(8) .
C22 C23 1.404(8) .
C23 C24 1.364(10) .
C24 C25 1.380(15) .
C25 C26 1.394(14) .
C26 C27 1.425(8) .
C27 C28 1.497(9) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 Pd1 P1 C15 -63.5(2) . .
F1 Pd1 P1 C15 149.8(8) . .
F2 Pd1 P1 C15 112.22(18) . .
Pd1 Pd1 P1 C15 114.54(18) 2 .
C1 Pd1 P1 C22 178.8(2) . .
F1 Pd1 P1 C22 32.2(9) . .
F2 Pd1 P1 C22 -5.4(2) . .
Pd1 Pd1 P1 C22 -3.1(2) 2 .
C1 Pd1 P1 C8 59.6(2) . .
F1 Pd1 P1 C8 -87.1(8) . .
F2 Pd1 P1 C8 -124.66(17) . .
Pd1 Pd1 P1 C8 -122.33(17) 2 .
C1 Pd1 F1 Pd1 175.34(11) . 2
F2 Pd1 F1 Pd1 0.0 . 2
P1 Pd1 F1 Pd1 -37.9(8) . 2
F1 Pd1 C1 C6 -115.7(3) . .
F2 Pd1 C1 C6 -91.1(7) . .
P1 Pd1 C1 C6 66.4(3) . .
Pd1 Pd1 C1 C6 -111.9(3) 2 .
F1 Pd1 C1 C2 51.3(3) . .
F2 Pd1 C1 C2 75.9(7) . .
P1 Pd1 C1 C2 -126.5(3) . .
Pd1 Pd1 C1 C2 55.1(4) 2 .
C1 Pd1 F2 Pd1 -25.0(6) . 2
F1 Pd1 F2 Pd1 0.0 . 2
P1 Pd1 F2 Pd1 177.59(3) . 2
C6 C1 C2 C3 -1.3(6) . .
Pd1 C1 C2 C3 -169.3(4) . .
C1 C2 C3 C4 -0.2(7) . .
C2 C3 C4 C5 0.9(7) . .
C2 C3 C4 C7 -178.5(5) . .
C3 C4 C5 C6 0.0(7) . .
C7 C4 C5 C6 179.4(5) . .
C4 C5 C6 C1 -1.6(7) . .
C2 C1 C6 C5 2.2(6) . .
Pd1 C1 C6 C5 169.4(3) . .
C15 P1 C8 C9 120.2(4) . .
C22 P1 C8 C9 -127.4(4) . .
Pd1 P1 C8 C9 -3.9(4) . .
C15 P1 C8 C13 -63.1(4) . .
C22 P1 C8 C13 49.2(5) . .
Pd1 P1 C8 C13 172.7(3) . .
C13 C8 C9 C10 -0.8(8) . .
P1 C8 C9 C10 176.0(4) . .
C8 C9 C10 C11 -0.2(8) . .
C9 C10 C11 C12 1.1(9) . .
C10 C11 C12 C13 -1.0(9) . .
C9 C8 C13 C12 0.9(7) . .
P1 C8 C13 C12 -175.6(4) . .
C9 C8 C13 C14 179.1(5) . .
P1 C8 C13 C14 2.6(7) . .
C11 C12 C13 C8 0.0(8) . .
C11 C12 C13 C14 -178.4(5) . .
C22 P1 C15 C16 -122.4(4) . .
C8 P1 C15 C16 -11.5(5) . .
Pd1 P1 C15 C16 116.5(4) . .
C22 P1 C15 C20 66.6(4) . .
C8 P1 C15 C20 177.5(4) . .
Pd1 P1 C15 C20 -54.5(5) . .
C20 C15 C16 C17 -0.3(8) . .
P1 C15 C16 C17 -171.6(4) . .
C15 C16 C17 C18 -1.0(9) . .
C16 C17 C18 C19 1.1(10) . .
C17 C18 C19 C20 0.2(11) . .
C18 C19 C20 C15 -1.6(9) . .
C18 C19 C20 C21 176.2(6) . .
C16 C15 C20 C19 1.6(7) . .
P1 C15 C20 C19 172.7(4) . .
C16 C15 C20 C21 -176.1(5) . .
P1 C15 C20 C21 -5.0(7) . .
C15 P1 C22 C27 -178.0(3) . .
C8 P1 C22 C27 68.3(4) . .
Pd1 P1 C22 C27 -58.0(4) . .
C15 P1 C22 C23 1.5(4) . .
C8 P1 C22 C23 -112.2(4) . .
Pd1 P1 C22 C23 121.4(3) . .
C27 C22 C23 C24 1.4(7) . .
P1 C22 C23 C24 -178.0(4) . .
C22 C23 C24 C25 -1.8(10) . .
C23 C24 C25 C26 2.1(12) . .
C24 C25 C26 C27 -2.2(10) . .
C23 C22 C27 C26 -1.5(7) . .
P1 C22 C27 C26 178.0(3) . .
C23 C22 C27 C28 177.7(4) . .
P1 C22 C27 C28 -2.8(6) . .
C25 C26 C27 C22 1.8(7) . .
C25 C26 C27 C28 -177.4(5) . .
