#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:51:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178726 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/37/4083716.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_4083716
loop_
_publ_author_name
'Contrella, Nathan D.'
'Sampson, Jessica R.'
'Jordan, Richard F.'
_publ_section_title
;
 Copolymerization of Ethylene and Methyl Acrylate by Cationic Palladium
 Catalysts That Contain Phosphine-Diethyl Phosphonate Ancillary Ligands
;
_journal_name_full               Organometallics
_journal_page_first              140623145555006
_journal_paper_doi               10.1021/om5004489
_journal_year                    2014
_chemical_formula_sum            'C25 H42 F6 N O3 P2 Pd Sb'
_chemical_formula_weight         808.69
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 124.79(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.542(7)
_cell_length_b                   13.030(6)
_cell_length_c                   19.490(7)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.58
_cell_measurement_theta_min      1.71
_cell_volume                     3033(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_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  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35200
_diffrn_reflns_theta_full        28.58
_diffrn_reflns_theta_max         28.58
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    1.654
_exptl_absorpt_correction_T_max  0.6923
_exptl_absorpt_correction_T_min  0.5874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
absorption corrections were made based on correspondance of
equivalent intensities usingprogram SADABS (G. Sheldrick, Bruker 
Analytical X-ray Systems, Madison, WI)
;
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.267
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         7462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0430
_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)+(0.0391P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0858
_reflns_number_gt                5912
_reflns_number_total             7462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5004489_si_001.cif
_cod_data_source_block           compound_3c
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4083716
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.3144(3) 0.0784(3) 0.6717(2) 0.0236(8) Uani 1 1 d .
H1A H 0.2968 0.0283 0.7002 0.035 Uiso 1 1 calc R
H1B H 0.3956 0.0815 0.6998 0.035 Uiso 1 1 calc R
H1C H 0.2784 0.0577 0.6134 0.035 Uiso 1 1 calc R
C2 C 0.1002(3) 0.1895(3) 0.4884(2) 0.0211(8) Uani 1 1 d .
C3 C 0.0058(3) 0.1597(3) 0.4142(2) 0.0279(9) Uani 1 1 d .
H3 H 0.0024 0.1651 0.3642 0.034 Uiso 1 1 calc R
C4 C -0.0839(3) 0.1224(3) 0.4115(2) 0.0304(9) Uani 1 1 d .
H4 H -0.1499 0.1016 0.3601 0.036 Uiso 1 1 calc R
C5 C -0.0765(3) 0.1156(3) 0.4846(2) 0.0268(9) Uani 1 1 d .
H5 H -0.1382 0.0905 0.4841 0.032 Uiso 1 1 calc R
C6 C 0.0196(3) 0.1447(3) 0.5585(2) 0.0237(8) Uani 1 1 d .
C7 C 0.1979(3) 0.2354(3) 0.4940(2) 0.0268(9) Uani 1 1 d .
H7A H 0.2110 0.3049 0.5170 0.040 Uiso 1 1 calc R
H7B H 0.1828 0.2383 0.4382 0.040 Uiso 1 1 calc R
H7C H 0.2645 0.1932 0.5306 0.040 Uiso 1 1 calc R
C8 C 0.0314(3) 0.1379(3) 0.6385(2) 0.0290(9) Uani 1 1 d .
H8A H 0.0939 0.0922 0.6765 0.043 Uiso 1 1 calc R
H8B H -0.0379 0.1105 0.6289 0.043 Uiso 1 1 calc R
H8C H 0.0459 0.2063 0.6635 0.043 Uiso 1 1 calc R
C9 C 0.1631(3) 0.5043(3) 0.5390(2) 0.0257(9) Uani 1 1 d .
H9A H 0.1068 0.4515 0.5269 0.031 Uiso 1 1 calc R
H9B H 0.1940 0.4871 0.5065 0.031 Uiso 1 1 calc R
C10 C 0.1080(3) 0.6059(3) 0.5122(2) 0.0287(9) Uani 1 1 d .
H10A H 0.0786 0.6239 0.5451 0.043 Uiso 1 1 calc R
H10B H 0.0462 0.6033 0.4528 0.043 Uiso 1 1 calc R
H10C H 0.1625 0.6577 0.5209 0.043 Uiso 1 1 calc R
C11 C 0.0974(3) 0.5213(3) 0.7319(2) 0.0257(9) Uani 1 1 d .
H11A H 0.1473 0.5410 0.7915 0.031 Uiso 1 1 calc R
H11B H 0.0790 0.4476 0.7286 0.031 Uiso 1 1 calc R
C12 C -0.0069(3) 0.5840(3) 0.6893(2) 0.0278(9) Uani 1 1 d .
H12A H 0.0125 0.6570 0.6955 0.042 Uiso 1 1 calc R
H12B H -0.0477 0.5699 0.7146 0.042 Uiso 1 1 calc R
H12C H -0.0542 0.5662 0.6298 0.042 Uiso 1 1 calc R
C13 C 0.3634(3) 0.4673(3) 0.7894(2) 0.0193(8) Uani 1 1 d .
C14 C 0.3905(3) 0.5649(3) 0.8238(2) 0.0208(8) Uani 1 1 d .
H14 H 0.3408 0.6203 0.7938 0.025 Uiso 1 1 calc R
C15 C 0.4889(3) 0.5828(3) 0.9013(2) 0.0222(8) Uani 1 1 d .
H15 H 0.5072 0.6504 0.9235 0.027 Uiso 1 1 calc R
C16 C 0.5601(3) 0.5030(3) 0.9460(2) 0.0200(8) Uani 1 1 d .
C17 C 0.5324(3) 0.4057(3) 0.9112(2) 0.0208(8) Uani 1 1 d .
H17 H 0.5818 0.3506 0.9424 0.025 Uiso 1 1 calc R
C18 C 0.4362(3) 0.3848(3) 0.8331(2) 0.0191(8) Uani 1 1 d .
C19 C 0.6669(3) 0.5179(3) 1.0295(2) 0.0253(9) Uani 1 1 d .
H19A H 0.7280 0.5296 1.0227 0.038 Uiso 1 1 calc R
H19B H 0.6831 0.4566 1.0637 0.038 Uiso 1 1 calc R
H19C H 0.6601 0.5775 1.0570 0.038 Uiso 1 1 calc R
C20 C 0.4602(3) 0.1758(3) 0.8842(2) 0.0232(8) Uani 1 1 d .
H20 H 0.5271 0.2088 0.9342 0.028 Uiso 1 1 calc R
C21 C 0.3670(3) 0.1778(3) 0.8969(3) 0.0311(10) Uani 1 1 d .
H21A H 0.3012 0.1426 0.8503 0.047 Uiso 1 1 calc R
H21B H 0.3477 0.2492 0.8993 0.047 Uiso 1 1 calc R
H21C H 0.3918 0.1430 0.9493 0.047 Uiso 1 1 calc R
C22 C 0.4923(3) 0.0661(3) 0.8804(2) 0.0296(9) Uani 1 1 d .
H22A H 0.5217 0.0320 0.9340 0.044 Uiso 1 1 calc R
H22B H 0.5498 0.0663 0.8690 0.044 Uiso 1 1 calc R
H22C H 0.4261 0.0291 0.8357 0.044 Uiso 1 1 calc R
C23 C 0.5333(3) 0.2468(3) 0.7774(2) 0.0223(8) Uani 1 1 d .
H23 H 0.5329 0.1751 0.7588 0.027 Uiso 1 1 calc R
C24 C 0.6508(3) 0.2676(3) 0.8522(3) 0.0320(10) Uani 1 1 d .
H24A H 0.7044 0.2486 0.8391 0.048 Uiso 1 1 calc R
H24B H 0.6655 0.2270 0.8998 0.048 Uiso 1 1 calc R
H24C H 0.6588 0.3407 0.8663 0.048 Uiso 1 1 calc R
C25 C 0.5043(3) 0.3168(3) 0.7057(2) 0.0285(9) Uani 1 1 d .
H25A H 0.5038 0.3882 0.7213 0.043 Uiso 1 1 calc R
H25B H 0.4302 0.2988 0.6563 0.043 Uiso 1 1 calc R
H25C H 0.5602 0.3089 0.6931 0.043 Uiso 1 1 calc R
F1 F 0.2409(2) 0.7289(2) 0.91902(17) 0.0558(8) Uani 1 1 d .
F2 F 0.2526(2) 0.9293(2) 0.93469(15) 0.0483(7) Uani 1 1 d .
F3 F 0.22429(19) 0.94701(18) 0.79015(14) 0.0369(6) Uani 1 1 d .
F4 F 0.2147(2) 0.74869(19) 0.77454(16) 0.0437(7) Uani 1 1 d .
F5 F 0.38710(18) 0.83081(19) 0.90904(14) 0.0375(6) Uani 1 1 d .
F6 F 0.07948(19) 0.84212(19) 0.80057(16) 0.0402(6) Uani 1 1 d .
N1 N 0.1076(2) 0.1800(2) 0.56024(18) 0.0208(7) Uani 1 1 d .
O1 O 0.1794(2) 0.35641(18) 0.67231(15) 0.0213(6) Uani 1 1 d .
O2 O 0.25328(19) 0.5020(2) 0.62802(15) 0.0220(6) Uani 1 1 d .
O3 O 0.15294(19) 0.54012(19) 0.69015(15) 0.0209(6) Uani 1 1 d .
P1 P 0.23149(8) 0.45841(7) 0.69164(6) 0.0192(2) Uani 1 1 d .
P2 P 0.42125(8) 0.25388(7) 0.79353(6) 0.0191(2) Uani 1 1 d .
Pd1 Pd 0.25743(2) 0.21746(2) 0.675679(17) 0.01877(8) Uani 1 1 d .
Sb1 Sb 0.23348(2) 0.83827(2) 0.855147(16) 0.02388(8) 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'
O O 0.0106 0.0060 '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'
Sb Sb -0.5866 1.5461 '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
N1 C2 C3 120.7(4)
N1 C2 C7 117.0(3)
C3 C2 C7 122.3(4)
C4 C3 C2 120.3(4)
C3 C4 C5 118.5(4)
C6 C5 C4 120.2(4)
N1 C6 C5 120.6(4)
N1 C6 C8 117.5(3)
C5 C6 C8 121.9(4)
O2 C9 C10 112.1(3)
O3 C11 C12 108.0(3)
C14 C13 C18 120.1(3)
C14 C13 P1 114.4(3)
C18 C13 P1 125.4(3)
C15 C14 C13 120.9(3)
C16 C15 C14 120.0(3)
C15 C16 C17 118.7(3)
C15 C16 C19 122.3(3)
C17 C16 C19 119.0(3)
C18 C17 C16 123.2(3)
C17 C18 C13 117.1(3)
C17 C18 P2 116.6(3)
C13 C18 P2 126.2(3)
C21 C20 C22 110.7(3)
C21 C20 P2 109.7(3)
C22 C20 P2 114.3(3)
C24 C23 C25 110.4(3)
C24 C23 P2 116.9(3)
C25 C23 P2 108.8(3)
C6 N1 C2 119.7(3)
C6 N1 Pd1 119.8(3)
C2 N1 Pd1 120.5(2)
P1 O1 Pd1 125.25(15)
C9 O2 P1 120.2(2)
C11 O3 P1 120.8(2)
O1 P1 O3 110.51(14)
O1 P1 O2 115.89(15)
O3 P1 O2 102.60(14)
O1 P1 C13 114.69(16)
O3 P1 C13 107.97(16)
O2 P1 C13 104.21(15)
C20 P2 C23 108.84(18)
C20 P2 C18 102.42(17)
C23 P2 C18 102.44(17)
C20 P2 Pd1 116.06(13)
C23 P2 Pd1 110.25(13)
C18 P2 Pd1 115.71(12)
C1 Pd1 N1 87.04(13)
C1 Pd1 O1 173.59(12)
N1 Pd1 O1 87.44(11)
C1 Pd1 P2 90.57(11)
N1 Pd1 P2 176.22(9)
O1 Pd1 P2 95.10(8)
F2 Sb1 F4 179.07(13)
F2 Sb1 F5 90.15(11)
F4 Sb1 F5 89.67(11)
F2 Sb1 F6 91.03(11)
F4 Sb1 F6 89.15(11)
F5 Sb1 F6 178.51(11)
F2 Sb1 F3 90.02(12)
F4 Sb1 F3 89.07(12)
F5 Sb1 F3 91.20(11)
F6 Sb1 F3 89.70(11)
F2 Sb1 F1 90.39(14)
F4 Sb1 F1 90.52(13)
F5 Sb1 F1 89.42(11)
F6 Sb1 F1 89.67(11)
F3 Sb1 F1 179.25(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 Pd1 2.011(4)
C2 N1 1.348(5)
C2 C3 1.364(5)
C2 C7 1.487(5)
C3 C4 1.364(5)
C4 C5 1.370(5)
C5 C6 1.369(5)
C6 N1 1.340(5)
C6 C8 1.472(5)
C9 O2 1.461(4)
C9 C10 1.481(5)
C11 O3 1.457(4)
C11 C12 1.490(5)
C13 C14 1.386(5)
C13 C18 1.405(5)
C13 P1 1.776(4)
C14 C15 1.385(5)
C15 C16 1.372(5)
C16 C17 1.385(5)
C16 C19 1.488(5)
C17 C18 1.385(5)
C18 P2 1.833(4)
C20 C21 1.511(5)
C20 C22 1.519(5)
C20 P2 1.826(4)
C23 C24 1.508(5)
C23 C25 1.513(5)
C23 P2 1.830(4)
F1 Sb1 1.855(3)
F2 Sb1 1.843(2)
F3 Sb1 1.854(2)
F4 Sb1 1.848(2)
F5 Sb1 1.851(2)
F6 Sb1 1.852(2)
N1 Pd1 2.111(3)
O1 P1 1.468(3)
O1 Pd1 2.118(2)
O2 P1 1.552(3)
O3 P1 1.550(3)
P2 Pd1 2.2208(14)
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
N1 C2 C3 C4 1.7(6)
C7 C2 C3 C4 -177.0(4)
C2 C3 C4 C5 0.0(6)
C3 C4 C5 C6 -0.8(6)
C4 C5 C6 N1 -0.1(6)
C4 C5 C6 C8 -179.5(4)
C18 C13 C14 C15 -0.2(5)
P1 C13 C14 C15 177.6(3)
C13 C14 C15 C16 -1.3(5)
C14 C15 C16 C17 1.3(5)
C14 C15 C16 C19 180.0(3)
C15 C16 C17 C18 0.3(5)
C19 C16 C17 C18 -178.5(3)
C16 C17 C18 C13 -1.8(5)
C16 C17 C18 P2 174.1(3)
C14 C13 C18 C17 1.7(5)
P1 C13 C18 C17 -175.9(3)
C14 C13 C18 P2 -173.7(3)
P1 C13 C18 P2 8.7(5)
C5 C6 N1 C2 1.8(5)
C8 C6 N1 C2 -178.8(3)
C5 C6 N1 Pd1 -177.0(3)
C8 C6 N1 Pd1 2.4(4)
C3 C2 N1 C6 -2.6(5)
C7 C2 N1 C6 176.2(3)
C3 C2 N1 Pd1 176.1(3)
C7 C2 N1 Pd1 -5.1(4)
C10 C9 O2 P1 97.4(3)
C12 C11 O3 P1 -153.9(3)
Pd1 O1 P1 O3 -174.97(15)
Pd1 O1 P1 O2 68.9(2)
Pd1 O1 P1 C13 -52.7(2)
C11 O3 P1 O1 46.2(3)
C11 O3 P1 O2 170.3(3)
C11 O3 P1 C13 -80.0(3)
C9 O2 P1 O1 51.2(3)
C9 O2 P1 O3 -69.3(3)
C9 O2 P1 C13 178.2(3)
C14 C13 P1 O1 -154.2(3)
C18 C13 P1 O1 23.5(4)
C14 C13 P1 O3 -30.5(3)
C18 C13 P1 O3 147.2(3)
C14 C13 P1 O2 78.1(3)
C18 C13 P1 O2 -104.2(3)
C21 C20 P2 C23 -178.1(3)
C22 C20 P2 C23 -53.1(3)
C21 C20 P2 C18 73.9(3)
C22 C20 P2 C18 -161.1(3)
C21 C20 P2 Pd1 -53.1(3)
C22 C20 P2 Pd1 71.9(3)
C24 C23 P2 C20 -50.5(3)
C25 C23 P2 C20 -176.4(3)
C24 C23 P2 C18 57.4(3)
C25 C23 P2 C18 -68.5(3)
C24 C23 P2 Pd1 -178.9(3)
C25 C23 P2 Pd1 55.2(3)
C17 C18 P2 C20 45.5(3)
C13 C18 P2 C20 -139.1(3)
C17 C18 P2 C23 -67.3(3)
C13 C18 P2 C23 108.1(3)
C17 C18 P2 Pd1 172.8(2)
C13 C18 P2 Pd1 -11.9(4)
C6 N1 Pd1 C1 98.2(3)
C2 N1 Pd1 C1 -80.6(3)
C6 N1 Pd1 O1 -78.6(3)
C2 N1 Pd1 O1 102.7(3)
P1 O1 Pd1 N1 -134.9(2)
P1 O1 Pd1 P2 42.27(18)
C20 P2 Pd1 C1 -65.21(18)
C23 P2 Pd1 C1 59.09(17)
C18 P2 Pd1 C1 174.72(17)
C20 P2 Pd1 O1 111.80(15)
C23 P2 Pd1 O1 -123.90(15)
C18 P2 Pd1 O1 -8.27(14)
