#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/50/4115036.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_4115036
loop_
_publ_author_name
'Darcy A. Culkin'
'John F. Hartwig'
_publ_section_title
;
 Synthesis, Characterization, and Reactivity of Arylpalladium Cyanoalkyl
 Complexes: Selection of Catalysts for the α-Arylation of Nitriles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9330
_journal_page_last               9331
_journal_paper_doi               10.1021/ja026584h
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C25 H28 N P Pd '
_chemical_formula_sum            'C25 H28 N P Pd'
_chemical_formula_weight         479.88
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             'Fri Sep 15 15:15:00 2001'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 94.839(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.992(1)
_cell_length_b                   8.6350(3)
_cell_length_c                   17.599(1)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    183.2
_cell_measurement_theta_max      0.0
_cell_measurement_theta_min      0.0
_cell_volume                     4541.6(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_diffrn_ambient_temperature      183.2
_diffrn_measurement_device       unknown
_diffrn_measurement_method       'omega scans with profile analysis'
_diffrn_orient_matrix_UB_11      0.00000
_diffrn_orient_matrix_UB_12      0.00000
_diffrn_orient_matrix_UB_13      0.00000
_diffrn_orient_matrix_UB_21      0.00000
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      0.00000
_diffrn_orient_matrix_UB_31      0.00000
_diffrn_orient_matrix_UB_32      0.00000
_diffrn_orient_matrix_UB_33      0.00000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoKalpha
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.00
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5562
_diffrn_reflns_theta_max         27.51
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       plate
_exptl_crystal_F_000             1968.00
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.568
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2796
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0308
_refine_ls_shift/esd_max         0.0007
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0309
_reflns_number_observed          2796
_reflns_number_total             5562
_reflns_observed_criterion       5.00
_cod_data_source_file            ja026584h_s2_3.cif
_cod_data_source_block           X-ray_Data_for_9.
_cod_original_cell_volume        4541.5(3)
_cod_original_sg_symbol_H-M      'C 2/c      '
_cod_original_formula_sum        'C25 H28 N P Pd '
_cod_database_code               4115036
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'1/2+x,1/2+y,   +z'
'   -x,   +y,1/2-z'
1/2-x,1/2+y,1/2-z
'   -x,   -y,   -z'
'1/2-x,1/2-y,   -z'
'   +x,   -y,1/2+z'
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
Pd(1) 0.834629(9) 0.18040(4) -0.01529(2) 0.02367(9) Uij
P(1) 0.87858(3) 0.0379(1) 0.07309(5) 0.0241(3) Uij
N(1) 0.7218(1) 0.3624(4) -0.0455(2) 0.029(1) Uij
C(1) 0.7953(1) 0.2992(5) -0.1072(2) 0.027(1) Uij
C(2) 0.7543(1) 0.3357(4) -0.0737(2) 0.024(1) Uij
C(3) 0.8140(1) 0.4463(5) -0.1395(2) 0.041(1) Uij
C(4) 0.7858(1) 0.1784(5) -0.1706(2) 0.043(1) Uij
C(5) 0.8895(1) 0.2501(5) -0.0625(2) 0.023(1) Uij
C(6) 0.9118(1) 0.3797(4) -0.0325(2) 0.026(1) Uij
C(7) 0.9509(1) 0.4327(4) -0.0602(2) 0.027(1) Uij
C(8) 0.9702(1) 0.3581(4) -0.1180(2) 0.026(1) Uij
C(9) 0.9481(1) 0.2303(5) -0.1495(2) 0.029(1) Uij
C(10) 0.9081(1) 0.1785(5) -0.1235(2) 0.027(1) Uij
C(11) 1.0141(1) 0.4124(5) -0.1439(2) 0.040(1) Uij
C(12) 0.8846(1) 0.1291(4) 0.1669(2) 0.025(1) Uij
C(13) 0.9236(1) 0.2040(5) 0.1946(2) 0.043(1) Uij
C(14) 0.9263(2) 0.2753(5) 0.2647(3) 0.053(2) Uij
C(15) 0.8910(2) 0.2748(5) 0.3080(2) 0.046(2) Uij
C(16) 0.8516(2) 0.2029(5) 0.2821(2) 0.044(2) Uij
C(17) 0.8485(1) 0.1296(5) 0.2115(2) 0.035(1) Uij
C(18) 0.8552(1) -0.1523(4) 0.0925(2) 0.024(1) Uij
C(19) 0.8729(1) -0.2411(5) 0.1539(2) 0.033(1) Uij
C(20) 0.8578(2) -0.3896(6) 0.1648(3) 0.046(2) Uij
C(21) 0.8247(2) -0.4498(5) 0.1160(3) 0.054(2) Uij
C(22) 0.8066(1) -0.3633(6) 0.0558(3) 0.054(2) Uij
C(23) 0.8218(1) -0.2155(5) 0.0432(2) 0.037(1) Uij
C(24) 0.9365(1) -0.0081(5) 0.0557(2) 0.033(1) Uij
C(25) 0.9394(1) -0.1311(5) -0.0062(2) 0.044(1) Uij
H(1) 0.8195 0.5203 -0.0998 0.0491 Uij
H(2) 0.8413 0.4234 -0.1611 0.0491 Uij
H(3) 0.7931 0.4873 -0.1778 0.0491 Uij
H(4) 0.7710 0.0918 -0.1510 0.0519 Uij
H(5) 0.7674 0.2230 -0.2114 0.0519 Uij
H(6) 0.8133 0.1457 -0.1888 0.0519 Uij
H(7) 0.9000 0.4337 0.0083 0.0309 Uij
H(8) 0.9648 0.5233 -0.0385 0.0327 Uij
H(9) 0.9604 0.1765 -0.1900 0.0351 Uij
H(10) 0.8932 0.0924 -0.1477 0.0327 Uij
H(11) 1.0142 0.5223 -0.1466 0.0477 Uij
H(12) 1.0378 0.3786 -0.1087 0.0477 Uij
H(13) 1.0179 0.3706 -0.1929 0.0477 Uij
H(14) 0.9487 0.2058 0.1650 0.0520 Uij
H(15) 0.9532 0.3256 0.2830 0.0642 Uij
H(16) 0.8934 0.3243 0.3564 0.0550 Uij
H(17) 0.8267 0.2035 0.3122 0.0524 Uij
H(18) 0.8215 0.0794 0.1936 0.0418 Uij
H(19) 0.8957 -0.1988 0.1887 0.0392 Uij
H(20) 0.8704 -0.4497 0.2063 0.0550 Uij
H(21) 0.8142 -0.5520 0.1235 0.0653 Uij
H(22) 0.7832 -0.4056 0.0223 0.0648 Uij
H(23) 0.8094 -0.1573 0.0008 0.0443 Uij
H(24) 0.9507 0.0837 0.0401 0.0392 Uij
H(25) 0.9517 -0.0451 0.1017 0.0392 Uij
H(26) 0.9257 -0.2239 0.0090 0.0528 Uij
H(27) 0.9245 -0.0952 -0.0526 0.0528 Uij
H(28) 0.9699 -0.1508 -0.0135 0.0528 Uij
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 200 0.003 0.002 'International Tables'
H 0 224 0.000 0.000 'International Tables'
N 0 8 0.006 0.003 'International Tables'
P 0 8 0.102 0.094 'International Tables'
Pd 0 8 -0.999 1.007 'International Tables'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
P(1) Pd(1) N(1) 90.10(8) yes
P(1) Pd(1) C(1) 174.3(1) yes
P(1) Pd(1) C(5) 89.9(1) yes
N(1) Pd(1) C(1) 92.9(1) yes
N(1) Pd(1) C(5) 171.0(1) yes
C(1) Pd(1) C(5) 87.9(1) yes
Pd(1) P(1) C(12) 112.7(1) yes
Pd(1) P(1) C(18) 113.5(1) yes
Pd(1) P(1) C(24) 119.9(1) yes
C(12) P(1) C(18) 103.3(2) yes
C(12) P(1) C(24) 102.8(2) yes
C(18) P(1) C(24) 102.8(2) yes
Pd(1) N(1) C(2) 157.8(3) yes
Pd(1) C(1) C(2) 103.1(2) yes
Pd(1) C(1) C(3) 118.5(2) yes
Pd(1) C(1) C(4) 106.0(2) yes
C(2) C(1) C(3) 109.0(3) yes
C(2) C(1) C(4) 109.5(3) yes
C(3) C(1) C(4) 110.3(3) yes
N(1) C(2) C(1) 178.4(4) yes
Pd(1) C(5) C(6) 118.2(3) yes
Pd(1) C(5) C(10) 125.7(3) yes
C(6) C(5) C(10) 116.1(3) yes
C(5) C(6) C(7) 121.9(3) yes
C(6) C(7) C(8) 121.9(3) yes
C(7) C(8) C(9) 117.1(3) yes
C(7) C(8) C(11) 120.8(4) yes
C(9) C(8) C(11) 122.1(4) yes
C(8) C(9) C(10) 121.5(3) yes
C(5) C(10) C(9) 121.5(4) yes
P(1) C(12) C(13) 122.3(3) yes
P(1) C(12) C(17) 119.4(3) yes
C(13) C(12) C(17) 118.2(4) yes
C(12) C(13) C(14) 120.4(4) yes
C(13) C(14) C(15) 121.0(4) yes
C(14) C(15) C(16) 120.3(4) yes
C(15) C(16) C(17) 119.4(4) yes
C(12) C(17) C(16) 120.7(4) yes
P(1) C(18) C(19) 120.7(3) yes
P(1) C(18) C(23) 120.5(3) yes
C(19) C(18) C(23) 118.6(4) yes
C(18) C(19) C(20) 120.7(4) yes
C(19) C(20) C(21) 120.0(4) yes
C(20) C(21) C(22) 120.0(4) yes
C(21) C(22) C(23) 120.8(4) yes
C(18) C(23) C(22) 119.9(4) yes
P(1) C(24) C(25) 112.4(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Pd(1) P(1) 2.308(1) yes
Pd(1) N(1) 2.111(3) yes
Pd(1) C(1) 2.177(4) yes
Pd(1) C(5) 1.998(3) yes
P(1) C(12) 1.824(4) yes
P(1) C(18) 1.829(4) yes
P(1) C(24) 1.834(4) yes
N(1) C(2) 1.152(4) yes
C(1) C(2) 1.443(5) yes
C(1) C(3) 1.519(5) yes
C(1) C(4) 1.537(5) yes
C(5) C(6) 1.386(5) yes
C(5) C(10) 1.396(5) yes
C(6) C(7) 1.385(5) yes
C(7) C(8) 1.373(5) yes
C(8) C(9) 1.380(5) yes
C(8) C(11) 1.503(5) yes
C(9) C(10) 1.392(5) yes
C(12) C(13) 1.390(5) yes
C(12) C(17) 1.390(5) yes
C(13) C(14) 1.374(5) yes
C(14) C(15) 1.356(6) yes
C(15) C(16) 1.378(6) yes
C(16) C(17) 1.390(5) yes
C(18) C(19) 1.394(5) yes
C(18) C(23) 1.379(5) yes
C(19) C(20) 1.379(6) yes
C(20) C(21) 1.358(6) yes
C(21) C(22) 1.371(6) yes
C(22) C(23) 1.380(6) yes
C(24) C(25) 1.529(5) yes
