#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:13:13 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178941 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/70/4117066.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_4117066
loop_
_publ_author_name
'Manuela Ohff'
'Andreas Ohff'
'Milko E. van der Boom'
'David Milstein'
_publ_section_title
;
 Highly Active Pd(II) PCP-Type Catalysts for the Heck Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11687
_journal_page_last               11688
_journal_paper_doi               10.1021/ja9729692
_journal_volume                  119
_journal_year                    1997
_chemical_formula_sum            'C38 H58 F3 O2 P2 Pd'
_chemical_formula_weight         772.18
_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
_cell_angle_alpha                107.90(3)
_cell_angle_beta                 109.15(3)
_cell_angle_gamma                95.55(3)
_cell_formula_units_Z            2
_cell_length_a                   11.738(2)
_cell_length_b                   12.183(2)
_cell_length_c                   15.259(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1913.6(9)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_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  0.0119
_diffrn_reflns_av_sigmaI/netI    0.0743
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7131
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         4.06
_exptl_absorpt_coefficient_mu    0.614
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             810
_refine_diff_density_max         1.604
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.052
_refine_ls_goodness_of_fit_obs   1.083
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         7000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_restrained_S_obs      1.083
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_obs          0.0645
_refine_ls_shift/esd_max         -0.027
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0936P)²+3.0117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1799
_refine_ls_wR_factor_obs         0.1523
_reflns_number_observed          5076
_reflns_number_total             7026
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja9729692_1.cif
_cod_data_source_block           m88
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0936P)^2^+3.0117P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0936P)^2^+3.0117P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1913.6(6)
_cod_database_code               4117066
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Pd1 Pd 0.79628(3) 0.85847(4) 0.60460(3) 0.01698(14) Uani 1 d .
P2 P 0.75270(11) 0.72596(12) 0.44252(11) 0.0167(3) Uani 1 d .
P3 P 0.73490(11) 0.96414(13) 0.73477(11) 0.0188(3) Uani 1 d .
O4 O 0.9298(4) 0.7741(4) 0.6802(4) 0.0314(10) Uani 1 d .
O5 O 1.0789(4) 0.9407(7) 0.7402(6) 0.060(2) Uani 1 d .
F6 F 1.2450(5) 0.8265(10) 0.8124(8) 0.125(4) Uani 1 d .
F7 F 1.1168(5) 0.7818(6) 0.8691(4) 0.065(2) Uani 1 d .
F8 F 1.1162(10) 0.6676(9) 0.7360(6) 0.162(6) Uani 1 d .
C1 C 0.6808(4) 0.9427(5) 0.5292(4) 0.0174(10) Uani 1 d .
H1A H 0.6875(4) 1.0230(5) 0.5712(4) 0.021 Uiso 1 calc R
H1B H 0.6955(4) 0.9432(5) 0.4704(4) 0.021 Uiso 1 calc R
C11 C 0.5597(4) 0.8648(5) 0.5034(4) 0.0159(10) Uani 1 d .
C12 C 0.5123(4) 0.7663(5) 0.4171(4) 0.0180(10) Uani 1 d .
C13 C 0.3959(4) 0.6959(5) 0.3920(4) 0.0197(11) Uani 1 d .
C14 C 0.3350(4) 0.7293(5) 0.4578(5) 0.0199(11) Uani 1 d .
H14 H 0.2557(4) 0.6862(5) 0.4395(5) 0.024 Uiso 1 calc R
C15 C 0.3850(4) 0.8216(5) 0.5476(4) 0.0189(11) Uani 1 d .
C16 C 0.5023(4) 0.8903(5) 0.5730(4) 0.0172(10) Uani 1 d .
C17 C 0.3347(5) 0.5884(6) 0.2978(5) 0.0287(13) Uani 1 d .
H17A H 0.3699(33) 0.5228(12) 0.3065(13) 0.043 Uiso 1 calc R
H17B H 0.3475(40) 0.6047(15) 0.2437(8) 0.043 Uiso 1 calc R
H17C H 0.2476(9) 0.5695(28) 0.2835(22) 0.043 Uiso 1 calc R
C18 C 0.3153(5) 0.8480(6) 0.6176(5) 0.0273(13) Uani 1 d .
H18A H 0.2967(40) 0.9247(19) 0.6260(29) 0.041 Uiso 1 calc R
H18B H 0.3655(19) 0.8465(44) 0.6809(13) 0.041 Uiso 1 calc R
H18C H 0.2397(23) 0.7893(25) 0.5898(19) 0.041 Uiso 1 calc R
C21 C 0.5950(4) 0.7322(5) 0.3585(4) 0.0186(11) Uani 1 d .
H21A H 0.6049(4) 0.7897(5) 0.3279(4) 0.022 Uiso 1 calc R
H21B H 0.5560(4) 0.6556(5) 0.3059(4) 0.022 Uiso 1 calc R
C22 C 0.8619(5) 0.7575(5) 0.3815(5) 0.0218(11) Uani 1 d .
C23 C 0.8572(5) 0.8804(6) 0.3750(5) 0.0279(13) Uani 1 d .
H23A H 0.8731(41) 0.9370(9) 0.4397(8) 0.042 Uiso 1 calc R
H23B H 0.7768(15) 0.8784(11) 0.3300(26) 0.042 Uiso 1 calc R
H23C H 0.9186(29) 0.9027(19) 0.3511(33) 0.042 Uiso 1 calc R
C24 C 0.8331(6) 0.6659(7) 0.2792(6) 0.036(2) Uani 1 d .
H24A H 0.8475(44) 0.5919(13) 0.2855(7) 0.054 Uiso 1 calc R
H24B H 0.8854(33) 0.6919(21) 0.2493(16) 0.054 Uiso 1 calc R
H24C H 0.7481(14) 0.6558(34) 0.2382(13) 0.054 Uiso 1 calc R
C25 C 0.9946(5) 0.7671(7) 0.4522(6) 0.035(2) Uani 1 d .
H25A H 1.0086(18) 0.8199(39) 0.5179(11) 0.052 Uiso 1 calc R
H25B H 1.0530(5) 0.7971(48) 0.4288(25) 0.052 Uiso 1 calc R
H25C H 1.0047(17) 0.6904(10) 0.4537(32) 0.052 Uiso 1 calc R
C26 C 0.7294(5) 0.5678(5) 0.4360(5) 0.0239(12) Uani 1 d .
C27 C 0.8533(5) 0.5326(6) 0.4778(6) 0.0308(14) Uani 1 d .
H27A H 0.8383(8) 0.4620(27) 0.4916(39) 0.046 Uiso 1 calc R
H27B H 0.9071(19) 0.5954(21) 0.5379(22) 0.046 Uiso 1 calc R
H27C H 0.8914(24) 0.5184(47) 0.4297(16) 0.046 Uiso 1 calc R
C28 C 0.6598(6) 0.5625(6) 0.5044(7) 0.036(2) Uani 1 d .
H28A H 0.7118(20) 0.6101(40) 0.5719(9) 0.054 Uiso 1 calc R
H28B H 0.6378(46) 0.4821(9) 0.4992(32) 0.054 Uiso 1 calc R
H28C H 0.5862(28) 0.5921(48) 0.4849(28) 0.054 Uiso 1 calc R
C29 C 0.6550(6) 0.4764(6) 0.3316(6) 0.038(2) Uani 1 d .
H29A H 0.6928(27) 0.4861(30) 0.2866(10) 0.058 Uiso 1 calc R
H29B H 0.5719(14) 0.4875(29) 0.3094(17) 0.058 Uiso 1 calc R
H29C H 0.6538(40) 0.3982(6) 0.3335(9) 0.058 Uiso 1 calc R
C31 C 0.5752(4) 0.9864(5) 0.6734(4) 0.0198(11) Uani 1 d .
H31A H 0.5301(4) 0.9884(5) 0.7168(4) 0.024 Uiso 1 calc R
H31B H 0.5827(4) 1.0622(5) 0.6651(4) 0.024 Uiso 1 calc R
C32 C 0.7099(5) 0.8750(6) 0.8110(5) 0.0250(12) Uani 1 d .
C33 C 0.6119(5) 0.7635(6) 0.7391(5) 0.0304(14) Uani 1 d .
H33A H 0.6373(22) 0.7238(24) 0.6862(20) 0.046 Uiso 1 calc R
H33B H 0.5348(12) 0.7846(7) 0.7120(28) 0.046 Uiso 1 calc R
H33C H 0.6020(33) 0.7120(19) 0.7740(10) 0.046 Uiso 1 calc R
C34 C 0.6640(8) 0.9380(8) 0.8920(7) 0.045(2) Uani 1 d .
H34A H 0.5979(39) 0.9733(46) 0.8648(14) 0.067 Uiso 1 calc R
H34B H 0.7307(17) 0.9984(37) 0.9457(22) 0.067 Uiso 1 calc R
H34C H 0.6347(53) 0.8818(13) 0.9165(32) 0.067 Uiso 1 calc R
C35 C 0.8284(6) 0.8345(8) 0.8577(6) 0.042(2) Uani 1 d .
H35A H 0.8898(21) 0.9017(12) 0.9088(31) 0.063 Uiso 1 calc R
H35B H 0.8593(32) 0.7986(49) 0.8073(10) 0.063 Uiso 1 calc R
H35C H 0.8098(14) 0.7782(43) 0.8860(42) 0.063 Uiso 1 calc R
C36 C 0.8234(5) 1.1194(6) 0.8161(5) 0.0263(12) Uani 1 d .
C37 C 0.9418(6) 1.1183(7) 0.8977(6) 0.038(2) Uani 1 d .
H37A H 0.9850(27) 1.0645(37) 0.8684(8) 0.057 Uiso 1 calc R
H37B H 0.9205(6) 1.0935(49) 0.9453(24) 0.057 Uiso 1 calc R
H37C H 0.9938(24) 1.1964(12) 0.9304(28) 0.057 Uiso 1 calc R
C38 C 0.8617(5) 1.1768(6) 0.7509(5) 0.0314(14) Uani 1 d .
H38A H 0.7894(6) 1.1853(42) 0.7031(25) 0.047 Uiso 1 calc R
H38B H 0.9048(41) 1.1278(22) 0.7169(29) 0.047 Uiso 1 calc R
H38C H 0.9150(38) 1.2532(19) 0.7919(7) 0.047 Uiso 1 calc R
C39 C 0.7495(7) 1.1977(7) 0.8661(6) 0.040(2) Uani 1 d .
H39A H 0.6740(27) 1.1975(43) 0.8161(7) 0.060 Uiso 1 calc R
H39B H 0.7979(23) 1.2772(14) 0.9013(38) 0.060 Uiso 1 calc R
H39C H 0.7307(48) 1.1672(31) 0.9119(32) 0.060 Uiso 1 calc R
C41 C 1.0386(6) 0.8389(8) 0.7291(6) 0.038(2) Uani 1 d .
C42 C 1.1304(6) 0.7782(8) 0.7873(6) 0.040(2) Uani 1 d .
C61 C 1.0983(13) 1.4501(15) 1.0379(13) 0.093(4) Uiso 1 d .
H61 H 1.1638(13) 1.4165(15) 1.0625(13) 0.112 Uiso 1 calc R
C62 C 0.9119(14) 1.5131(17) 1.0440(15) 0.104(4) Uiso 1 d .
H62 H 0.8547(14) 1.5203(17) 1.0745(15) 0.125 Uiso 1 calc R
C63 C 1.0203(14) 1.4628(17) 1.0763(15) 0.106(5) Uiso 1 d .
H63 H 1.0311(14) 1.4385(17) 1.1301(15) 0.127 Uiso 1 calc R
C64 C 0.4863(9) 0.6810(11) 0.9595(9) 0.232(15) Uiso 1 d G
H64 H 0.4163(9) 0.6250(11) 0.9116(9) 0.278 Uiso 1 calc R
C65 C 0.6011(11) 0.6513(9) 0.9824(9) 0.099(4) Uiso 1 d G
H65 H 0.6080(15) 0.5755(10) 0.9499(13) 0.119 Uiso 1 calc R
C66 C 0.7057(8) 0.7349(11) 1.0540(9) 0.121(5) Uiso 1 d G
H66 H 0.7825(9) 0.7151(15) 1.0693(13) 0.145 Uiso 1 calc R
C67 C 0.6955(9) 0.8482(11) 1.1026(9) 0.122(6) Uiso 1 d G
H67 H 0.7654(11) 0.9042(13) 1.1505(13) 0.146 Uiso 1 calc R
C68 C 0.5806(11) 0.8779(10) 1.0797(10) 0.157(8) Uiso 1 d G
H68 H 0.5738(16) 0.9537(11) 1.1123(14) 0.189 Uiso 1 calc R
C69 C 0.4761(8) 0.7943(12) 1.0081(10) 0.099(4) Uiso 1 d G
H69 H 0.3993(10) 0.8142(16) 0.9928(15) 0.119 Uiso 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'
O O 0.0106 0.0060 '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'
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 O4 175.3(2) . .
C1 Pd1 P2 82.4(2) . .
O4 Pd1 P2 96.14(14) . .
C1 Pd1 P3 81.8(2) . .
O4 Pd1 P3 101.24(14) . .
P2 Pd1 P3 152.22(5) . .
C26 P2 C22 111.9(3) . .
C26 P2 C21 102.7(3) . .
C22 P2 C21 105.3(2) . .
C26 P2 Pd1 111.2(2) . .
C22 P2 Pd1 116.2(2) . .
C21 P2 Pd1 108.4(2) . .
C36 P3 C32 111.4(3) . .
C36 P3 C31 102.3(3) . .
C32 P3 C31 103.1(2) . .
C36 P3 Pd1 118.4(2) . .
C32 P3 Pd1 113.0(2) . .
C31 P3 Pd1 106.8(2) . .
C41 O4 Pd1 114.5(4) . .
C11 C1 Pd1 99.5(3) . .
C12 C11 C16 122.2(5) . .
C12 C11 C1 119.7(5) . .
C16 C11 C1 117.9(5) . .
C11 C12 C13 119.0(5) . .
C11 C12 C21 117.8(4) . .
C13 C12 C21 122.8(5) . .
C14 C13 C12 117.6(5) . .
C14 C13 C17 119.4(5) . .
C12 C13 C17 123.0(5) . .
C15 C14 C13 124.1(5) . .
C14 C15 C16 117.9(5) . .
C14 C15 C18 120.8(5) . .
C16 C15 C18 121.3(5) . .
C15 C16 C11 118.6(5) . .
C15 C16 C31 124.1(5) . .
C11 C16 C31 117.2(4) . .
C12 C21 P2 111.0(4) . .
C24 C22 C23 110.3(6) . .
C24 C22 C25 110.6(5) . .
C23 C22 C25 106.3(5) . .
C24 C22 P2 113.8(4) . .
C23 C22 P2 107.6(4) . .
C25 C22 P2 107.8(4) . .
C28 C26 C29 109.2(5) . .
C28 C26 C27 107.1(6) . .
C29 C26 C27 108.1(5) . .
C28 C26 P2 105.5(4) . .
C29 C26 P2 114.6(5) . .
C27 C26 P2 112.1(4) . .
C16 C31 P3 113.0(4) . .
C33 C32 C34 107.9(5) . .
C33 C32 C35 106.9(6) . .
C34 C32 C35 109.6(6) . .
C33 C32 P3 106.8(4) . .
C34 C32 P3 114.4(5) . .
C35 C32 P3 111.0(4) . .
C38 C36 C37 107.8(5) . .
C38 C36 C39 108.0(6) . .
C37 C36 C39 108.5(6) . .
C38 C36 P3 107.6(5) . .
C37 C36 P3 110.3(5) . .
C39 C36 P3 114.4(4) . .
O5 C41 O4 130.2(6) . .
O5 C41 C42 116.5(7) . .
O4 C41 C42 113.2(7) . .
F6 C42 F8 106.2(8) . .
F6 C42 F7 106.2(7) . .
F8 C42 F7 106.4(10) . .
F6 C42 C41 113.1(7) . .
F8 C42 C41 112.3(7) . .
F7 C42 C41 112.2(5) . .
C63 C61 C62 120.2(16) . 2_787
C61 C62 C63 114.4(15) 2_787 .
C61 C63 C62 125.4(19) . .
C65 C64 C69 120.0 . .
C64 C65 C66 120.0 . .
C67 C66 C65 120.0 . .
C66 C67 C68 120.0 . .
C69 C68 C67 120.0 . .
C68 C69 C64 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.046(5) .
Pd1 O4 2.167(4) .
Pd1 P2 2.354(2) .
Pd1 P3 2.381(2) .
P2 C26 1.887(6) .
P2 C22 1.889(5) .
P2 C21 1.899(5) .
P3 C36 1.879(7) .
P3 C32 1.885(6) .
P3 C31 1.888(5) .
O4 C41 1.276(9) .
O5 C41 1.223(10) .
F6 C42 1.293(9) .
F7 C42 1.298(9) .
F8 C42 1.296(12) .
C1 C11 1.489(7) .
C11 C12 1.380(8) .
C11 C16 1.410(8) .
C12 C13 1.405(7) .
C12 C21 1.527(7) .
C13 C14 1.401(8) .
C13 C17 1.510(8) .
C14 C15 1.373(9) .
C15 C16 1.405(7) .
C15 C18 1.525(8) .
C16 C31 1.514(8) .
C22 C24 1.518(10) .
C22 C23 1.536(9) .
C22 C25 1.545(8) .
C26 C28 1.533(9) .
C26 C29 1.533(10) .
C26 C27 1.545(7) .
C32 C33 1.525(9) .
C32 C34 1.531(10) .
C32 C35 1.544(8) .
C36 C38 1.530(9) .
C36 C37 1.536(8) .
C36 C39 1.547(10) .
C41 C42 1.557(9) .
C61 C63 1.24(2) .
C61 C62 1.43(2) 2_787
C62 C61 1.43(2) 2_787
C62 C63 1.47(2) .
C64 C65 1.39 .
C64 C69 1.39 .
C65 C66 1.39 .
C66 C67 1.39 .
C67 C68 1.39 .
C68 C69 1.39 .
