#------------------------------------------------------------------------------
#$Date: 2018-09-27 07:13:35 +0300 (Thu, 27 Sep 2018) $
#$Revision: 211196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/69/1506973.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_1506973
loop_
_publ_author_name
'Xiao, Ji-Chang'
'Twamley, Brendan'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 An ionic liquid-coordinated palladium complex: a highly efficient and
 recyclable catalyst for the Heck reaction.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              3845
_journal_page_last               3847
_journal_paper_doi               10.1021/ol048327i
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C36 H62 Cl2 F12 N8 P2 Pd'
_chemical_formula_weight         1074.18
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.18(3)
_cell_angle_beta                 93.91(3)
_cell_angle_gamma                106.21(3)
_cell_formula_units_Z            1
_cell_length_a                   9.882(2)
_cell_length_b                   10.758(2)
_cell_length_c                   12.086(2)
_cell_measurement_reflns_used    5377
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      25.51
_cell_measurement_theta_min      2.18
_cell_volume                     1147.0(5)
_computing_cell_refinement       'Bruker SAINT+ v. 6.36a'
_computing_data_collection       'Bruker SMART v. 5.626'
_computing_data_reduction        'Bruker SAINT+ v. 6.36a'
_computing_molecular_graphics    'XP, Bruker SHELXTL v. 6.12'
_computing_publication_material  'XCIF, Bruker SHELXTL v. 6.12'
_computing_structure_refinement  'XL, Bruker SHELXTL v. 6.12'
_computing_structure_solution    'XS, Bruker SHELXTL v. 6.12'
_diffrn_ambient_temperature      85(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker/Siemens SMART APEX'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12845
_diffrn_reflns_theta_full        25.54
_diffrn_reflns_theta_max         25.54
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        <0.01
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.8490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (SAINT+, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.076
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0495
_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)+(0.0451P)²+2.0938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                3603
_reflns_number_total             4248
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048327isi20040824_074951.cif
_cod_data_source_block           bt631
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        1147.1(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.0083(3) 0.9329(3) 0.1371(3) 0.0177(7) Uani 1 1 d .
C2 C -0.1070(4) 0.8438(4) 0.1594(4) 0.0217(9) Uani 1 1 d .
H2 H -0.2023 0.8110 0.1171 0.026 Uiso 1 1 calc R
C3 C -0.0634(4) 0.8104(4) 0.2510(4) 0.0228(9) Uani 1 1 d .
H3 H -0.1213 0.7496 0.2836 0.027 Uiso 1 1 calc R
N4 N 0.0794(4) 0.8805(4) 0.2877(3) 0.0226(8) Uani 1 1 d .
C5 C 0.1193(4) 0.9542(4) 0.2165(3) 0.0185(8) Uani 1 1 d .
C6 C 0.2654(4) 1.0445(4) 0.2282(3) 0.0192(8) Uani 1 1 d .
N7 N 0.3074(3) 1.1830(3) 0.2617(3) 0.0207(7) Uani 1 1 d .
C8 C 0.4507(4) 1.2292(4) 0.2592(3) 0.0234(9) Uani 1 1 d .
H8 H 0.5085 1.3231 0.2794 0.028 Uiso 1 1 calc R
C9 C 0.4944(4) 1.1160(4) 0.2226(4) 0.0241(9) Uani 1 1 d .
H9 H 0.5888 1.1158 0.2121 0.029 Uiso 1 1 calc R
N10 N 0.3782(3) 1.0020(3) 0.2035(3) 0.0180(7) Uani 1 1 d .
C11 C 0.3724(4) 0.8548(4) 0.1573(4) 0.0233(9) Uani 1 1 d .
H11A H 0.2740 0.7960 0.1156 0.028 Uiso 1 1 calc R
H11B H 0.3954 0.8270 0.2248 0.028 Uiso 1 1 calc R
C12 C 0.4762(4) 0.8301(5) 0.0722(4) 0.0268(10) Uani 1 1 d .
H12A H 0.5754 0.8798 0.1163 0.032 Uiso 1 1 calc R
H12B H 0.4611 0.8686 0.0102 0.032 Uiso 1 1 calc R
C13 C 0.4574(5) 0.6759(5) 0.0130(4) 0.0343(11) Uani 1 1 d .
H13A H 0.5382 0.6659 -0.0295 0.041 Uiso 1 1 calc R
H13B H 0.4611 0.6355 0.0754 0.041 Uiso 1 1 calc R
C14 C 0.3182(6) 0.5950(6) -0.0742(5) 0.0463(13) Uani 1 1 d .
H14A H 0.2375 0.5987 -0.0317 0.069 Uiso 1 1 calc R
H14B H 0.3144 0.4981 -0.1121 0.069 Uiso 1 1 calc R
H14C H 0.3125 0.6359 -0.1352 0.069 Uiso 1 1 calc R
C15 C 0.2168(4) 1.2727(4) 0.2944(4) 0.0246(9) Uani 1 1 d .
H15A H 0.2602 1.3465 0.3733 0.030 Uiso 1 1 calc R
H15B H 0.1212 1.2169 0.3004 0.030 Uiso 1 1 calc R
C16 C 0.2002(4) 1.3388(4) 0.2032(4) 0.0242(9) Uani 1 1 d .
H16A H 0.1648 1.2653 0.1231 0.029 Uiso 1 1 calc R
H16B H 0.2948 1.4011 0.2022 0.029 Uiso 1 1 calc R
C17 C 0.0967(5) 1.4212(4) 0.2309(4) 0.0296(10) Uani 1 1 d .
H17A H 0.0014 1.3582 0.2292 0.036 Uiso 1 1 calc R
H17B H 0.1304 1.4925 0.3120 0.036 Uiso 1 1 calc R
C18 C 0.0834(5) 1.4916(5) 0.1424(4) 0.0371(11) Uani 1 1 d .
H18A H 0.1771 1.5561 0.1455 0.056 Uiso 1 1 calc R
H18B H 0.0151 1.5428 0.1625 0.056 Uiso 1 1 calc R
H18C H 0.0494 1.4212 0.0620 0.056 Uiso 1 1 calc R
C19 C 0.1715(5) 0.8667(6) 0.3837(4) 0.0404(12) Uani 1 1 d .
H19A H 0.1769 0.7711 0.3570 0.048 Uiso 1 1 calc R
H19B H 0.2697 0.9314 0.3968 0.048 Uiso 1 1 calc R
C20 C 0.1177(6) 0.8963(6) 0.4979(4) 0.0451(13) Uani 1 1 d .
H20A H 0.0151 0.8417 0.4830 0.054 Uiso 1 1 calc R
H20B H 0.1262 0.9960 0.5311 0.054 Uiso 1 1 calc R
C21 C 0.1999(5) 0.8612(6) 0.5892(4) 0.0408(12) Uani 1 1 d .
H21A H 0.3035 0.9056 0.5941 0.049 Uiso 1 1 calc R
H21B H 0.1759 0.9042 0.6680 0.049 Uiso 1 1 calc R
C22 C 0.1743(6) 0.7097(6) 0.5671(5) 0.0496(14) Uani 1 1 d .
H22A H 0.0712 0.6597 0.5451 0.074 Uiso 1 1 calc R
H22B H 0.2125 0.6997 0.6395 0.074 Uiso 1 1 calc R
H22C H 0.2224 0.6712 0.5022 0.074 Uiso 1 1 calc R
Pd1 Pd 0.0000 1.0000 0.0000 0.01420(14) Uani 1 2 d S
Cl1 Cl -0.18366(10) 1.08035(11) 0.06437(8) 0.0223(2) Uani 1 1 d .
P1 P 0.43579(12) 0.28991(12) 0.60752(10) 0.0252(3) Uani 1 1 d .
F1 F 0.5961(3) 0.3239(3) 0.6697(3) 0.0447(7) Uani 1 1 d .
F2 F 0.3765(3) 0.2029(3) 0.6877(3) 0.0435(7) Uani 1 1 d .
F3 F 0.4265(4) 0.4251(4) 0.7046(3) 0.0718(11) Uani 1 1 d .
F4 F 0.4937(3) 0.3777(3) 0.5279(3) 0.0465(8) Uani 1 1 d .
F5 F 0.4487(4) 0.1557(3) 0.5092(3) 0.0675(10) Uani 1 1 d .
F6 F 0.2760(3) 0.2523(4) 0.5441(3) 0.0706(12) 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'
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'
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'
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
C5 N1 C2 106.2(3) . .
C5 N1 Pd1 129.7(3) . .
C2 N1 Pd1 123.9(3) . .
C3 C2 N1 109.2(3) . .
C3 C2 H2 125.4 . .
N1 C2 H2 125.4 . .
C2 C3 N4 107.1(4) . .
C2 C3 H3 126.5 . .
N4 C3 H3 126.5 . .
C5 N4 C3 107.1(3) . .
C5 N4 C19 128.5(4) . .
C3 N4 C19 124.3(4) . .
N1 C5 N4 110.4(3) . .
N1 C5 C6 125.7(4) . .
N4 C5 C6 123.9(3) . .
N10 C6 N7 108.4(3) . .
N10 C6 C5 125.7(4) . .
N7 C6 C5 125.9(4) . .
C6 N7 C8 108.5(3) . .
C6 N7 C15 126.7(3) . .
C8 N7 C15 124.8(3) . .
C9 C8 N7 107.1(4) . .
C9 C8 H8 126.5 . .
N7 C8 H8 126.5 . .
C8 C9 N10 107.6(4) . .
C8 C9 H9 126.2 . .
N10 C9 H9 126.2 . .
C6 N10 C9 108.4(3) . .
C6 N10 C11 124.4(3) . .
C9 N10 C11 127.1(3) . .
N10 C11 C12 111.9(3) . .
N10 C11 H11A 109.2 . .
C12 C11 H11A 109.2 . .
N10 C11 H11B 109.2 . .
C12 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
C11 C12 C13 111.9(4) . .
C11 C12 H12A 109.2 . .
C13 C12 H12A 109.2 . .
C11 C12 H12B 109.2 . .
C13 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C14 C13 C12 113.3(4) . .
C14 C13 H13A 108.9 . .
C12 C13 H13A 108.9 . .
C14 C13 H13B 108.9 . .
C12 C13 H13B 108.9 . .
H13A C13 H13B 107.7 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N7 C15 C16 111.4(3) . .
N7 C15 H15A 109.4 . .
C16 C15 H15A 109.4 . .
N7 C15 H15B 109.4 . .
C16 C15 H15B 109.4 . .
H15A C15 H15B 108.0 . .
C15 C16 C17 111.5(4) . .
C15 C16 H16A 109.3 . .
C17 C16 H16A 109.3 . .
C15 C16 H16B 109.3 . .
C17 C16 H16B 109.3 . .
H16A C16 H16B 108.0 . .
C18 C17 C16 111.8(4) . .
C18 C17 H17A 109.3 . .
C16 C17 H17A 109.3 . .
C18 C17 H17B 109.3 . .
C16 C17 H17B 109.3 . .
H17A C17 H17B 107.9 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C20 C19 N4 113.1(4) . .
C20 C19 H19A 109.0 . .
N4 C19 H19A 109.0 . .
C20 C19 H19B 109.0 . .
N4 C19 H19B 109.0 . .
H19A C19 H19B 107.8 . .
C19 C20 C21 112.3(4) . .
C19 C20 H20A 109.1 . .
C21 C20 H20A 109.1 . .
C19 C20 H20B 109.1 . .
C21 C20 H20B 109.1 . .
H20A C20 H20B 107.9 . .
C22 C21 C20 117.1(4) . .
C22 C21 H21A 108.0 . .
C20 C21 H21A 108.0 . .
C22 C21 H21B 108.0 . .
C20 C21 H21B 108.0 . .
H21A C21 H21B 107.3 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
N1 Pd1 N1 180.00(16) . 2_575
N1 Pd1 Cl1 89.43(9) . .
N1 Pd1 Cl1 90.57(9) 2_575 .
N1 Pd1 Cl1 90.57(9) . 2_575
N1 Pd1 Cl1 89.43(9) 2_575 2_575
Cl1 Pd1 Cl1 180.00(5) . 2_575
F3 P1 F5 178.6(2) . .
F3 P1 F4 89.38(19) . .
F5 P1 F4 89.61(18) . .
F3 P1 F6 91.6(2) . .
F5 P1 F6 89.4(2) . .
F4 P1 F6 90.70(16) . .
F3 P1 F2 90.14(19) . .
F5 P1 F2 90.88(18) . .
F4 P1 F2 179.36(18) . .
F6 P1 F2 88.90(16) . .
F3 P1 F1 89.7(2) . .
F5 P1 F1 89.4(2) . .
F4 P1 F1 89.78(16) . .
F6 P1 F1 178.6(2) . .
F2 P1 F1 90.64(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.322(5) .
N1 C2 1.375(5) .
N1 Pd1 2.019(3) .
C2 C3 1.349(6) .
C2 H2 0.9500 .
C3 N4 1.363(5) .
C3 H3 0.9500 .
N4 C5 1.358(5) .
N4 C19 1.497(5) .
C5 C6 1.465(5) .
C6 N10 1.335(5) .
C6 N7 1.338(5) .
N7 C8 1.369(5) .
N7 C15 1.474(5) .
C8 C9 1.354(6) .
C8 H8 0.9500 .
C9 N10 1.367(5) .
C9 H9 0.9500 .
N10 C11 1.479(5) .
C11 C12 1.515(6) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.526(6) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.514(7) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.517(6) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.518(6) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.517(6) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 C20 1.481(7) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.531(7) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.505(8) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
Pd1 N1 2.019(3) 2_575
Pd1 Cl1 2.2963(11) .
Pd1 Cl1 2.2963(11) 2_575
P1 F3 1.571(3) .
P1 F5 1.584(3) .
P1 F4 1.586(3) .
P1 F6 1.587(3) .
P1 F2 1.589(3) .
P1 F1 1.594(3) .
