#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:45:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178822 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/76/4107654.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_4107654
loop_
_publ_author_name
'Stefan Erhardt'
'Vladimir V. Grushin'
'Alison H. Kilpatrick'
'Stuart A. Macgregor'
'William J. Marshall'
'D. Christopher Roe'
_publ_section_title
;
 Mechanisms of Catalyst Poisoning in Palladium-Catalyzed Cyanation of
 Haloarenes. Remarkably Facile C-N Bond Activation in the
 [(Ph3P)4Pd]/[Bu4N]+CN-System
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4828
_journal_page_last               4845
_journal_paper_doi               10.1021/ja078298h
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C38 H30 N2 P2 Pd'
_chemical_formula_weight         682.98
_chemical_name_systematic
;
 ?
;
_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                110.8770(10)
_cell_angle_beta                 93.0840(10)
_cell_angle_gamma                108.0970(10)
_cell_formula_units_Z            1
_cell_length_a                   9.1134(8)
_cell_length_b                   9.7354(8)
_cell_length_c                   10.2226(9)
_cell_measurement_temperature    293(2)
_cell_volume                     791.57(12)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12835
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       ireg.block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.958
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0249
_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)+(0.0270P)²+0.3532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0631
_reflns_number_gt                3691
_reflns_number_total             3903
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja078298h-file001_4.cif
_cod_data_source_block           07150
_cod_database_code               4107654
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
Pd1 Pd 0.5000 0.5000 0.5000 0.01814(6) Uani 1 2 d S
P1 P 0.48771(5) 0.27506(5) 0.30473(4) 0.01759(9) Uani 1 1 d .
N1 N 0.2167(2) 0.3088(2) 0.60221(19) 0.0354(4) Uani 1 1 d .
C1 C 0.3209(2) 0.3763(2) 0.56436(19) 0.0244(4) Uani 1 1 d .
C2 C 0.3669(2) 0.2602(2) 0.14907(18) 0.0201(3) Uani 1 1 d .
C3 C 0.3855(2) 0.3970(2) 0.1258(2) 0.0279(4) Uani 1 1 d .
H3A H 0.4528 0.4937 0.1924 0.034 Uiso 1 1 calc R
C4 C 0.3035(2) 0.3886(3) 0.0033(2) 0.0358(5) Uani 1 1 d .
H4A H 0.3171 0.4798 -0.0123 0.043 Uiso 1 1 calc R
C5 C 0.2023(2) 0.2466(3) -0.0955(2) 0.0375(5) Uani 1 1 d .
H5A H 0.1481 0.2420 -0.1776 0.045 Uiso 1 1 calc R
C6 C 0.1815(3) 0.1109(3) -0.0722(2) 0.0379(5) Uani 1 1 d .
H6A H 0.1124 0.0149 -0.1384 0.045 Uiso 1 1 calc R
C7 C 0.2635(2) 0.1173(2) 0.0496(2) 0.0301(4) Uani 1 1 d .
H7A H 0.2491 0.0257 0.0647 0.036 Uiso 1 1 calc R
C8 C 0.4128(2) 0.08124(19) 0.31174(18) 0.0231(3) Uani 1 1 d .
C9 C 0.2612(2) 0.0229(2) 0.3351(2) 0.0315(4) Uani 1 1 d .
H9A H 0.1986 0.0846 0.3507 0.038 Uiso 1 1 calc R
C10 C 0.2024(3) -0.1276(2) 0.3352(2) 0.0395(5) Uani 1 1 d .
H10A H 0.1008 -0.1663 0.3506 0.047 Uiso 1 1 calc R
C11 C 0.2957(3) -0.2189(2) 0.3125(2) 0.0429(6) Uani 1 1 d .
H11A H 0.2562 -0.3196 0.3117 0.052 Uiso 1 1 calc R
C12 C 0.4462(3) -0.1621(2) 0.2913(3) 0.0438(5) Uani 1 1 d .
H12A H 0.5088 -0.2235 0.2777 0.053 Uiso 1 1 calc R
C13 C 0.5053(3) -0.0124(2) 0.2901(2) 0.0322(4) Uani 1 1 d .
H13A H 0.6070 0.0254 0.2747 0.039 Uiso 1 1 calc R
C14 C 0.6794(2) 0.29096(19) 0.25639(18) 0.0204(3) Uani 1 1 d .
C15 C 0.7079(2) 0.2802(2) 0.12144(19) 0.0241(3) Uani 1 1 d .
H15A H 0.6260 0.2588 0.0504 0.029 Uiso 1 1 calc R
C16 C 0.8593(2) 0.3017(2) 0.0929(2) 0.0338(4) Uani 1 1 d .
H16A H 0.8791 0.2972 0.0035 0.041 Uiso 1 1 calc R
C17 C 0.9802(2) 0.3295(2) 0.1975(2) 0.0371(5) Uani 1 1 d .
H17A H 1.0810 0.3433 0.1780 0.044 Uiso 1 1 calc R
C18 C 0.9520(2) 0.3369(2) 0.3309(2) 0.0359(5) Uani 1 1 d .
H18A H 1.0330 0.3529 0.4001 0.043 Uiso 1 1 calc R
C19 C 0.8028(2) 0.3203(2) 0.3610(2) 0.0295(4) Uani 1 1 d .
H19A H 0.7847 0.3287 0.4518 0.035 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'
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
C1 Pd1 C1 180.0 . 2_666
C1 Pd1 P1 88.05(5) . 2_666
C1 Pd1 P1 91.95(5) 2_666 2_666
C1 Pd1 P1 91.95(5) . .
C1 Pd1 P1 88.05(5) 2_666 .
P1 Pd1 P1 179.999(17) 2_666 .
C14 P1 C2 104.80(8) . .
C14 P1 C8 104.39(8) . .
C2 P1 C8 105.46(8) . .
C14 P1 Pd1 111.40(5) . .
C2 P1 Pd1 109.01(5) . .
C8 P1 Pd1 120.55(6) . .
N1 C1 Pd1 178.06(16) . .
C7 C2 C3 119.15(16) . .
C7 C2 P1 122.44(13) . .
C3 C2 P1 118.32(14) . .
C4 C3 C2 119.90(18) . .
C5 C4 C3 120.70(18) . .
C4 C5 C6 119.76(18) . .
C5 C6 C7 120.2(2) . .
C6 C7 C2 120.27(18) . .
C9 C8 C13 118.92(17) . .
C9 C8 P1 120.53(14) . .
C13 C8 P1 120.53(14) . .
C8 C9 C10 120.3(2) . .
C11 C10 C9 119.8(2) . .
C12 C11 C10 120.49(19) . .
C11 C12 C13 120.1(2) . .
C12 C13 C8 120.4(2) . .
C15 C14 C19 119.35(16) . .
C15 C14 P1 122.54(13) . .
C19 C14 P1 118.08(13) . .
C14 C15 C16 119.90(17) . .
C17 C16 C15 120.03(19) . .
C18 C17 C16 120.38(18) . .
C17 C18 C19 119.82(19) . .
C18 C19 C14 120.48(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.0016(18) .
Pd1 C1 2.0016(18) 2_666
Pd1 P1 2.3453(4) 2_666
Pd1 P1 2.3453(4) .
P1 C14 1.8160(17) .
P1 C2 1.8202(17) .
P1 C8 1.8257(17) .
N1 C1 1.148(2) .
C2 C7 1.390(2) .
C2 C3 1.396(2) .
C3 C4 1.386(3) .
C4 C5 1.376(3) .
C5 C6 1.382(3) .
C6 C7 1.389(3) .
C8 C9 1.391(3) .
C8 C13 1.394(3) .
C9 C10 1.396(3) .
C10 C11 1.383(3) .
C11 C12 1.371(4) .
C12 C13 1.393(3) .
C14 C15 1.391(2) .
C14 C19 1.395(2) .
C15 C16 1.393(3) .
C16 C17 1.383(3) .
C17 C18 1.381(3) .
C18 C19 1.383(3) .
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
C1 Pd1 P1 C14 -150.32(8) .
C1 Pd1 P1 C14 29.68(8) 2_666
P1 Pd1 P1 C14 -24(10) 2_666
C1 Pd1 P1 C2 94.51(8) .
C1 Pd1 P1 C2 -85.49(8) 2_666
P1 Pd1 P1 C2 -140(10) 2_666
C1 Pd1 P1 C8 -27.55(9) .
C1 Pd1 P1 C8 152.45(9) 2_666
P1 Pd1 P1 C8 98(10) 2_666
C1 Pd1 C1 N1 -104(17) 2_666
P1 Pd1 C1 N1 40(5) 2_666
P1 Pd1 C1 N1 -140(5) .
C14 P1 C2 C7 99.26(16) .
C8 P1 C2 C7 -10.60(17) .
Pd1 P1 C2 C7 -141.38(14) .
C14 P1 C2 C3 -77.40(15) .
C8 P1 C2 C3 172.73(14) .
Pd1 P1 C2 C3 41.96(15) .
C7 C2 C3 C4 -1.2(3) .
P1 C2 C3 C4 175.54(15) .
C2 C3 C4 C5 0.7(3) .
C3 C4 C5 C6 0.3(3) .
C4 C5 C6 C7 -0.6(3) .
C5 C6 C7 C2 0.0(3) .
C3 C2 C7 C6 0.9(3) .
P1 C2 C7 C6 -175.74(16) .
C14 P1 C8 C9 -174.90(15) .
C2 P1 C8 C9 -64.74(16) .
Pd1 P1 C8 C9 59.01(16) .
C14 P1 C8 C13 3.42(17) .
C2 P1 C8 C13 113.58(16) .
Pd1 P1 C8 C13 -122.66(14) .
C13 C8 C9 C10 -0.7(3) .
P1 C8 C9 C10 177.67(15) .
C8 C9 C10 C11 0.2(3) .
C9 C10 C11 C12 0.7(3) .
C10 C11 C12 C13 -1.1(3) .
C11 C12 C13 C8 0.6(3) .
C9 C8 C13 C12 0.3(3) .
P1 C8 C13 C12 -178.09(16) .
C2 P1 C14 C15 -4.22(16) .
C8 P1 C14 C15 106.42(15) .
Pd1 P1 C14 C15 -121.95(13) .
C2 P1 C14 C19 173.60(14) .
C8 P1 C14 C19 -75.76(15) .
Pd1 P1 C14 C19 55.86(15) .
C19 C14 C15 C16 -1.2(3) .
P1 C14 C15 C16 176.60(14) .
C14 C15 C16 C17 1.7(3) .
C15 C16 C17 C18 -0.3(3) .
C16 C17 C18 C19 -1.6(3) .
C17 C18 C19 C14 2.1(3) .
C15 C14 C19 C18 -0.7(3) .
P1 C14 C19 C18 -178.59(15) .
