#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:19:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178559 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/67/4066710.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_4066710
loop_
_publ_author_name
'D’Amora, Angela'
'Fanfoni, Lidia'
'Cozzula, Daniela'
'Guidolin, Nicol'
'Zangrando, Ennio'
'Felluga, Fulvia'
'Gladiali, Serafino'
'Benedetti, Fabio'
'Milani, Barbara'
_publ_section_title
;
 Addressing the Poly- to Oligo-ketone Selectivity in Styrene Carbonylation
 Catalyzed by Palladium/bpy Complexes. Effect of the 6-Alkyl Substitution
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              4472
_journal_paper_doi               10.1021/om100585x
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety
'C16 H18 N3 Pd 1+, 0.5(P F6 1-), 0.5(P F6 1-)'
_chemical_formula_sum            'C16 H18 F6 N3 P Pd'
_chemical_formula_weight         503.70
_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                 109.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.155(3)
_cell_length_b                   22.725(4)
_cell_length_c                   12.775(3)
_cell_measurement_temperature    293(2)
_cell_volume                     3874.4(16)
_computing_cell_refinement       'Denzo (Otwinowski & Minor 1997)'
_computing_data_collection       'XPRESS (MacScience, 2002)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 1.80.05 (Farrugia, 1999)'
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELX97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type
'Enraf-Nonius dip1030 image plate  diffractometer'
_diffrn_measurement_method       'φ-scans with narrow frames'
_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  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25725
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    1.101
_exptl_absorpt_correction_T_max  0.8742
_exptl_absorpt_correction_T_min  0.6825
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56
Linear fit to sin(theta)/lambda - 12 parameters
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhomboid
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0722
_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)+(0.1606P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2234
_reflns_number_gt                1687
_reflns_number_total             2722
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om100585x_si_003.cif
_cod_data_source_block           3b'
_cod_original_cell_volume        3874.3(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4066710
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
Pd Pd 0.15332(5) 0.25817(3) 0.24866(6) 0.1013(4) Uani 1 1 d .
N1 N 0.1453(4) 0.1818(3) 0.3262(5) 0.0641(15) Uani 1 1 d .
N2 N 0.1157(5) 0.2901(4) 0.3868(7) 0.108(2) Uani 1 1 d U
N3 N 0.1668(6) 0.3377(4) 0.1821(8) 0.115(2) Uani 1 1 d .
C1 C 0.1460(8) 0.1271(6) 0.2834(10) 0.125(3) Uani 1 1 d .
C2 C 0.1453(10) 0.0779(6) 0.3505(15) 0.154(5) Uani 1 1 d .
H2 H 0.1449 0.0403 0.3217 0.184 Uiso 1 1 calc R
C3 C 0.1451(9) 0.0841(6) 0.4525(13) 0.137(4) Uani 1 1 d .
H3 H 0.1512 0.0516 0.4985 0.164 Uiso 1 1 calc R
C4 C 0.1359(9) 0.1389(7) 0.4893(11) 0.141(4) Uani 1 1 d .
H4 H 0.1304 0.1459 0.5588 0.169 Uiso 1 1 calc R
C5 C 0.1353(7) 0.1852(5) 0.4132(14) 0.135(5) Uani 1 1 d .
C6 C 0.1141(7) 0.2463(4) 0.4569(10) 0.098(3) Uani 1 1 d U
C7 C 0.0942(9) 0.2596(6) 0.5534(12) 0.130(4) Uani 1 1 d .
H7 H 0.0940 0.2303 0.6042 0.156 Uiso 1 1 calc R
C8 C 0.0737(9) 0.3203(9) 0.5729(12) 0.145(5) Uani 1 1 d .
H8 H 0.0571 0.3307 0.6350 0.174 Uiso 1 1 calc R
C9 C 0.0791(9) 0.3609(7) 0.5002(13) 0.135(4) Uani 1 1 d .
H9 H 0.0672 0.4002 0.5124 0.162 Uiso 1 1 calc R
C10 C 0.1011(8) 0.3464(5) 0.4108(11) 0.123(3) Uani 1 1 d .
H10 H 0.1066 0.3760 0.3628 0.147 Uiso 1 1 calc R
C11 C 0.1954(9) 0.2243(6) 0.1246(10) 0.131(4) Uani 1 1 d .
H11A H 0.1422 0.2306 0.0544 0.157 Uiso 1 1 calc R
H11B H 0.2544 0.2450 0.1218 0.157 Uiso 1 1 calc R
C12 C 0.2194(12) 0.1559(7) 0.1400(11) 0.161(5) Uani 1 1 d .
H12A H 0.2300 0.1409 0.0737 0.193 Uiso 1 1 calc R
H12B H 0.2810 0.1503 0.2018 0.193 Uiso 1 1 calc R
C13 C 0.1395(11) 0.1223(5) 0.1605(13) 0.137(4) Uani 1 1 d .
H13 H 0.0756 0.1398 0.1153 0.164 Uiso 1 1 calc R
C14 C 0.1417(12) 0.0579(6) 0.1188(14) 0.173(5) Uani 1 1 d .
H14A H 0.1303 0.0582 0.0404 0.259 Uiso 1 1 calc R
H14C H 0.0903 0.0352 0.1335 0.259 Uiso 1 1 calc R
H14B H 0.2059 0.0406 0.1569 0.259 Uiso 1 1 calc R
C15 C 0.1770(8) 0.3802(5) 0.1447(9) 0.109(3) Uani 1 1 d .
C16 C 0.1869(9) 0.4346(6) 0.0961(12) 0.144(4) Uani 1 1 d .
H16A H 0.1953 0.4655 0.1497 0.217 Uiso 1 1 calc R
H16B H 0.1279 0.4420 0.0334 0.217 Uiso 1 1 calc R
H16C H 0.2444 0.4333 0.0721 0.217 Uiso 1 1 calc R
P1 P 0.0000 0.1093(2) 0.7500 0.1140(12) Uani 1 2 d S
F1 F 0.0501(12) 0.0594(7) 0.8289(14) 0.320(8) Uani 1 1 d .
F2 F 0.0896(8) 0.1127(10) 0.7226(12) 0.354(12) Uani 1 1 d .
F3 F 0.0461(11) 0.1451(8) 0.8497(13) 0.315(9) Uani 1 1 d .
P2 P 0.0000 0.47620(18) 0.7500 0.1167(13) Uani 1 2 d S
F4 F -0.0736(12) 0.4363(11) 0.7012(13) 0.398(14) Uani 1 1 d .
F5 F -0.077(2) 0.5205(8) 0.6996(17) 0.461(16) Uani 1 1 d .
F6 F 0.0215(16) 0.4745(8) 0.6456(13) 0.346(10) 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'
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
N1 Pd C11 97.8(4) . .
N1 Pd N3 175.7(3) . .
C11 Pd N3 85.3(5) . .
N1 Pd N2 79.4(3) . .
C11 Pd N2 176.3(4) . .
N3 Pd N2 97.3(4) . .
C5 N1 C1 117.5(10) . .
C5 N1 Pd 117.0(7) . .
C1 N1 Pd 125.4(6) . .
C6 N2 C10 120.9(11) . .
C6 N2 Pd 111.3(7) . .
C10 N2 Pd 127.7(9) . .
C15 N3 Pd 177.4(10) . .
N1 C1 C2 118.6(12) . .
N1 C1 C13 117.9(10) . .
C2 C1 C13 123.4(13) . .
C3 C2 C1 121.4(13) . .
C2 C3 C4 118.4(13) . .
C3 C4 C5 114.9(14) . .
N1 C5 C4 128.4(14) . .
N1 C5 C6 119.8(9) . .
C4 C5 C6 111.7(15) . .
N2 C6 C7 118.9(10) . .
N2 C6 C5 111.9(10) . .
C7 C6 C5 129.2(12) . .
C6 C7 C8 118.2(13) . .
C9 C8 C7 118.7(13) . .
C10 C9 C8 120.9(14) . .
C9 C10 N2 122.2(13) . .
C12 C11 Pd 112.5(9) . .
C13 C12 C11 112.8(11) . .
C12 C13 C1 110.9(11) . .
C12 C13 C14 109.0(12) . .
C1 C13 C14 114.3(12) . .
N3 C15 C16 178.3(12) . .
F2 P1 F2 173.8(19) . 2_556
F2 P1 F3 90.5(10) . .
F2 P1 F3 86.0(9) 2_556 .
F2 P1 F3 86.0(9) . 2_556
F2 P1 F3 90.5(10) 2_556 2_556
F3 P1 F3 112.8(16) . 2_556
F2 P1 F1 86.9(9) . .
F2 P1 F1 97.7(12) 2_556 .
F3 P1 F1 82.2(9) . .
F3 P1 F1 163.5(13) 2_556 .
F2 P1 F1 97.7(12) . 2_556
F2 P1 F1 86.9(10) 2_556 2_556
F3 P1 F1 163.5(13) . 2_556
F3 P1 F1 82.2(9) 2_556 2_556
F1 P1 F1 84.0(15) . 2_556
F4 P2 F4 97(2) . 2_556
F4 P2 F5 178.1(17) . 2_556
F4 P2 F5 85.1(13) 2_556 2_556
F4 P2 F5 85.1(13) . .
F4 P2 F5 178.1(18) 2_556 .
F5 P2 F5 93(2) 2_556 .
F4 P2 F6 92.3(11) . 2_556
F4 P2 F6 85.8(9) 2_556 2_556
F5 P2 F6 88.1(12) 2_556 2_556
F5 P2 F6 93.9(11) . 2_556
F4 P2 F6 85.8(9) . .
F4 P2 F6 92.3(11) 2_556 .
F5 P2 F6 93.9(11) 2_556 .
F5 P2 F6 88.1(12) . .
F6 P2 F6 177.1(14) 2_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd N1 2.020(7) .
Pd C11 2.022(12) .
Pd N3 2.033(11) .
Pd N2 2.134(9) .
N1 C5 1.170(17) .
N1 C1 1.359(15) .
N2 C6 1.345(13) .
N2 C10 1.346(13) .
N3 C15 1.108(12) .
C1 C2 1.411(18) .
C1 C13 1.546(18) .
C2 C3 1.312(18) .
C3 C4 1.352(18) .
C4 C5 1.431(16) .
C5 C6 1.561(17) .
C6 C7 1.39(2) .
C7 C8 1.449(19) .
C8 C9 1.329(18) .
C9 C10 1.322(16) .
C11 C12 1.588(19) .
C12 C13 1.459(19) .
C13 C14 1.560(17) .
C15 C16 1.413(17) .
P1 F2 1.426(11) .
P1 F2 1.426(11) 2_556
P1 F3 1.468(11) .
P1 F3 1.468(11) 2_556
P1 F1 1.527(12) .
P1 F1 1.527(12) 2_556
P2 F4 1.365(13) .
P2 F4 1.365(13) 2_556
P2 F5 1.463(14) 2_556
P2 F5 1.463(14) .
P2 F6 1.464(11) 2_556
P2 F6 1.464(11) .
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
C11 Pd N1 C5 170.0(8)
N3 Pd N1 C5 34(4)
N2 Pd N1 C5 -7.5(7)
C11 Pd N1 C1 -13.2(8)
N3 Pd N1 C1 -149(4)
N2 Pd N1 C1 169.4(7)
N1 Pd N2 C6 5.0(6)
C11 Pd N2 C6 -38(7)
N3 Pd N2 C6 -172.2(6)
N1 Pd N2 C10 -179.3(8)
C11 Pd N2 C10 137(7)
N3 Pd N2 C10 3.6(8)
N1 Pd N3 C15 102(22)
C11 Pd N3 C15 -34(22)
N2 Pd N3 C15 143(22)
C5 N1 C1 C2 -6.5(14)
Pd N1 C1 C2 176.7(8)
C5 N1 C1 C13 169.0(10)
Pd N1 C1 C13 -7.8(13)
N1 C1 C2 C3 -0.8(19)
C13 C1 C2 C3 -176.0(13)
C1 C2 C3 C4 6(2)
C2 C3 C4 C5 -4.8(19)
C1 N1 C5 C4 8.7(15)
Pd N1 C5 C4 -174.3(8)
C1 N1 C5 C6 -168.7(8)
Pd N1 C5 C6 8.4(11)
C3 C4 C5 N1 -3.1(17)
C3 C4 C5 C6 174.5(10)
C10 N2 C6 C7 1.8(15)
Pd N2 C6 C7 177.9(9)
C10 N2 C6 C5 -178.7(8)
Pd N2 C6 C5 -2.6(9)
N1 C5 C6 N2 -3.7(12)
C4 C5 C6 N2 178.6(8)
N1 C5 C6 C7 175.8(12)
C4 C5 C6 C7 -1.9(16)
N2 C6 C7 C8 1.4(18)
C5 C6 C7 C8 -178.0(8)
C6 C7 C8 C9 -2.9(18)
C7 C8 C9 C10 1.1(18)
C8 C9 C10 N2 2.2(18)
C6 N2 C10 C9 -3.8(16)
Pd N2 C10 C9 -179.2(8)
N1 Pd C11 C12 -7.1(10)
N3 Pd C11 C12 169.9(10)
N2 Pd C11 C12 36(7)
Pd C11 C12 C13 50.9(14)
C11 C12 C13 C1 -80.3(14)
C11 C12 C13 C14 153.0(12)
N1 C1 C13 C12 55.7(15)
C2 C1 C13 C12 -129.0(13)
N1 C1 C13 C14 179.5(10)
C2 C1 C13 C14 -5.2(19)
Pd N3 C15 C16 145(37)
