#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:19:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178559 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/67/4066705.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_4066705
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         'C14 H17 Cl N2 O Pd'
_chemical_formula_sum            'C14 H17 Cl N2 O Pd'
_chemical_formula_weight         371.15
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.112(4)
_cell_length_b                   9.467(3)
_cell_length_c                   19.243(4)
_cell_measurement_temperature    293(2)
_cell_volume                     2935.2(13)
_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 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33849
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_T_max  0.6187
_exptl_absorpt_correction_T_min  0.5232
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56
Quadratic fit to sin(theta)/lambda - 18 parameters
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.833
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0412
_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)+(0.0653P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                1759
_reflns_number_total             3093
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om100585x_si_003.cif
_cod_data_source_block           1a
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               4066705
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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 0.086196(18) 0.41456(3) 0.152033(16) 0.07065(16) Uani 1 1 d .
Cl1 Cl -0.00370(7) 0.24350(12) 0.11088(6) 0.0909(4) Uani 1 1 d .
N1 N 0.1692(2) 0.5470(3) 0.19977(17) 0.0720(9) Uani 1 1 d .
N2 N 0.1990(2) 0.3842(3) 0.08641(17) 0.0690(8) Uani 1 1 d .
O1 O 0.1619(3) 0.1787(5) -0.0674(2) 0.1356(15) Uani 1 1 d .
C1 C 0.1526(3) 0.6375(5) 0.2514(2) 0.0829(12) Uani 1 1 d .
H1 H 0.0976 0.6492 0.2648 0.100 Uiso 1 1 calc R
C2 C 0.2118(3) 0.7134(5) 0.2854(2) 0.0890(13) Uani 1 1 d .
H2 H 0.1973 0.7749 0.3210 0.107 Uiso 1 1 calc R
C3 C 0.2927(3) 0.6975(5) 0.2661(3) 0.0868(13) Uani 1 1 d .
H3 H 0.3345 0.7464 0.2892 0.104 Uiso 1 1 calc R
C4 C 0.3117(3) 0.6075(4) 0.2119(2) 0.0785(12) Uani 1 1 d .
H4 H 0.3663 0.5984 0.1969 0.094 Uiso 1 1 calc R
C5 C 0.2490(3) 0.5310(4) 0.1800(2) 0.0680(10) Uani 1 1 d .
C6 C 0.2662(3) 0.4327(4) 0.1219(2) 0.0718(11) Uani 1 1 d .
C7 C 0.3460(3) 0.3928(5) 0.1047(3) 0.1002(15) Uani 1 1 d .
H7 H 0.3910 0.4242 0.1308 0.120 Uiso 1 1 calc R
C8 C 0.3579(3) 0.3056(6) 0.0482(3) 0.1150(18) Uani 1 1 d .
H8 H 0.4108 0.2739 0.0368 0.138 Uiso 1 1 calc R
C9 C 0.2917(3) 0.2668(6) 0.0097(3) 0.1037(15) Uani 1 1 d .
H9 H 0.2994 0.2122 -0.0300 0.124 Uiso 1 1 calc R
C10 C 0.2126(3) 0.3079(4) 0.0288(2) 0.0777(11) Uani 1 1 d .
C11 C -0.0049(3) 0.4595(6) 0.2214(3) 0.1046(16) Uani 1 1 d .
H11A H -0.0142 0.5597 0.2224 0.157 Uiso 1 1 calc R
H11B H 0.0116 0.4279 0.2668 0.157 Uiso 1 1 calc R
H11C H -0.0550 0.4123 0.2079 0.157 Uiso 1 1 calc R
C12 C 0.1378(3) 0.2746(5) -0.0159(3) 0.0910(13) Uani 1 1 d .
H12 H 0.0945 0.2318 0.0130 0.109 Uiso 1 1 calc R
C13 C 0.1045(4) 0.4083(6) -0.0490(4) 0.135(2) Uani 1 1 d .
H13A H 0.0569 0.3859 -0.0769 0.202 Uiso 1 1 calc R
H13B H 0.1466 0.4498 -0.0777 0.202 Uiso 1 1 calc R
H13C H 0.0888 0.4740 -0.0133 0.202 Uiso 1 1 calc R
C14 C 0.1076(5) 0.0810(6) -0.0834(5) 0.174(4) Uani 1 1 d .
H14A H 0.0595 0.1244 -0.1037 0.261 Uiso 1 1 calc R
H14B H 0.0917 0.0309 -0.0421 0.261 Uiso 1 1 calc R
H14C H 0.1318 0.0163 -0.1160 0.261 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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
C11 Pd N1 92.79(18)
C11 Pd N2 171.22(17)
N1 Pd N2 78.51(13)
C11 Pd Cl1 85.38(14)
N1 Pd Cl1 171.96(9)
N2 Pd Cl1 103.07(9)
C1 N1 C5 118.2(4)
C1 N1 Pd 126.4(3)
C5 N1 Pd 115.2(3)
C10 N2 C6 117.9(4)
C10 N2 Pd 132.0(3)
C6 N2 Pd 108.7(3)
C14 O1 C12 116.1(5)
N1 C1 C2 123.7(4)
C1 C2 C3 118.8(4)
C2 C3 C4 119.0(4)
C3 C4 C5 119.7(4)
N1 C5 C4 120.7(4)
N1 C5 C6 117.5(4)
C4 C5 C6 121.8(4)
N2 C6 C7 121.9(4)
N2 C6 C5 116.3(4)
C7 C6 C5 121.8(4)
C8 C7 C6 118.8(5)
C9 C8 C7 119.1(5)
C8 C9 C10 120.4(5)
N2 C10 C9 121.4(4)
N2 C10 C12 116.9(4)
C9 C10 C12 121.6(4)
O1 C12 C10 108.5(4)
O1 C12 C13 110.0(5)
C10 C12 C13 110.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd C11 2.028(4)
Pd N1 2.051(3)
Pd N2 2.232(3)
Pd Cl1 2.3124(11)
N1 C1 1.339(5)
N1 C5 1.349(5)
N2 C10 1.342(5)
N2 C6 1.359(5)
O1 C14 1.310(6)
O1 C12 1.398(5)
C1 C2 1.360(6)
C2 C3 1.364(6)
C3 C4 1.381(6)
C4 C5 1.387(6)
C5 C6 1.481(6)
C6 C7 1.381(6)
C7 C8 1.378(7)
C8 C9 1.350(7)
C9 C10 1.383(6)
C10 C12 1.513(6)
C12 C13 1.516(7)
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 C1 -8.1(4)
N2 Pd N1 C1 173.1(4)
Cl1 Pd N1 C1 -84.7(8)
C11 Pd N1 C5 166.2(3)
N2 Pd N1 C5 -12.6(3)
Cl1 Pd N1 C5 89.6(8)
C11 Pd N2 C10 175.3(12)
N1 Pd N2 C10 -176.9(4)
Cl1 Pd N2 C10 11.2(4)
C11 Pd N2 C6 9.3(13)
N1 Pd N2 C6 17.2(3)
Cl1 Pd N2 C6 -154.8(2)
C5 N1 C1 C2 -0.5(7)
Pd N1 C1 C2 173.7(3)
N1 C1 C2 C3 0.1(7)
C1 C2 C3 C4 1.5(6)
C2 C3 C4 C5 -2.7(6)
C1 N1 C5 C4 -0.8(6)
Pd N1 C5 C4 -175.6(3)
C1 N1 C5 C6 -178.7(4)
Pd N1 C5 C6 6.4(5)
C3 C4 C5 N1 2.3(6)
C3 C4 C5 C6 -179.8(4)
C10 N2 C6 C7 -7.3(6)
Pd N2 C6 C7 160.9(4)
C10 N2 C6 C5 172.7(3)
Pd N2 C6 C5 -19.1(4)
N1 C5 C6 N2 9.9(5)
C4 C5 C6 N2 -168.0(4)
N1 C5 C6 C7 -170.1(4)
C4 C5 C6 C7 12.0(7)
N2 C6 C7 C8 2.6(7)
C5 C6 C7 C8 -177.4(5)
C6 C7 C8 C9 2.8(9)
C7 C8 C9 C10 -3.4(9)
C6 N2 C10 C9 6.7(6)
Pd N2 C10 C9 -158.2(4)
C6 N2 C10 C12 -170.7(4)
Pd N2 C10 C12 24.4(6)
C8 C9 C10 N2 -1.5(8)
C8 C9 C10 C12 175.8(5)
C14 O1 C12 C10 142.2(6)
C14 O1 C12 C13 -97.1(7)
N2 C10 C12 O1 -171.7(4)
C9 C10 C12 O1 10.9(7)
N2 C10 C12 C13 67.8(6)
C9 C10 C12 C13 -109.6(6)
