#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:35:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178658 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/69/4076997.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_4076997
loop_
_publ_author_name
'Vicente, José'
'Abad, José-Antonio'
'Martínez-Viviente, Eloísa'
'Jones, Peter G.'
_publ_section_title
;
 Study of the Reactivity of 2-Acetyl-, 2-Cyano-, 2-Formyl-, and
 2-Vinylphenyl Palladium(II) Complexes. Mono- and Triinsertion of an
 Isocyanide into the Pd−C Bond. A 2-Cyanophenyl Palladium Complex
 as a Ligand
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              4454
_journal_paper_doi               10.1021/om020380s
_journal_volume                  21
_journal_year                    2002
_chemical_formula_sum            'C27 H24 F3 O5 P Pd S'
_chemical_formula_weight         654.89
_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     Patterson
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.101(3)
_cell_angle_beta                 107.928(3)
_cell_angle_gamma                94.628(3)
_cell_formula_units_Z            2
_cell_length_a                   10.0477(8)
_cell_length_b                   11.0958(11)
_cell_length_c                   12.7645(11)
_cell_measurement_reflns_used    5745
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     1344.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω- & φ-scan'
_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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25576
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment
'water H free with SADI, rigid methyl, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         7811
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0356P)²+0.2200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0605
_reflns_number_gt                7045
_reflns_number_total             7811
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om020380s.cif
_cod_data_source_block           brnocl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (16
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (26 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4076997
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Pd Pd 0.519694(10) 0.808650(9) 0.339357(8) 0.01652(4) Uani 1 1 d .
P P 0.38374(3) 0.64584(3) 0.24357(3) 0.01606(7) Uani 1 1 d .
O1 O 0.65377(10) 0.96229(9) 0.42444(8) 0.0223(2) Uani 1 1 d .
O2 O 0.40572(11) 0.82278(10) 0.45518(9) 0.02057(19) Uani 1 1 d D
H01 H 0.465(2) 0.830(2) 0.5128(15) 0.041(6) Uiso 1 1 d D
H02 H 0.375(2) 0.8851(16) 0.4464(16) 0.030(5) Uiso 1 1 d D
C11 C 0.65013(14) 0.81453(13) 0.25005(11) 0.0185(2) Uani 1 1 d .
C12 C 0.75899(14) 0.91147(12) 0.29143(11) 0.0188(2) Uani 1 1 d .
C13 C 0.86530(15) 0.93326(13) 0.24257(12) 0.0225(3) Uani 1 1 d .
H13 H 0.9367 0.9987 0.2715 0.027 Uiso 1 1 calc R
C14 C 0.86560(16) 0.85871(14) 0.15178(12) 0.0245(3) Uani 1 1 d .
H14 H 0.9370 0.8726 0.1181 0.029 Uiso 1 1 calc R
C15 C 0.76035(16) 0.76364(14) 0.11077(12) 0.0248(3) Uani 1 1 d .
H15 H 0.7606 0.7122 0.0489 0.030 Uiso 1 1 calc R
C16 C 0.65436(15) 0.74211(14) 0.15859(12) 0.0226(3) Uani 1 1 d .
H16 H 0.5834 0.6766 0.1283 0.027 Uiso 1 1 calc R
C17 C 0.75295(14) 0.98726(13) 0.38667(11) 0.0203(3) Uani 1 1 d .
C18 C 0.85741(16) 1.09304(14) 0.44320(13) 0.0258(3) Uani 1 1 d .
H18A H 0.8087 1.1662 0.4421 0.031 Uiso 1 1 calc R
H18B H 0.9274 1.1050 0.4046 0.031 Uiso 1 1 calc R
H18C H 0.9045 1.0771 0.5199 0.031 Uiso 1 1 calc R
C21 C 0.24230(14) 0.59551(12) 0.29789(10) 0.0178(2) Uani 1 1 d .
C22 C 0.22784(15) 0.48125(13) 0.33516(11) 0.0212(3) Uani 1 1 d .
H22 H 0.2955 0.4260 0.3358 0.025 Uiso 1 1 calc R
C23 C 0.11355(16) 0.44800(14) 0.37163(12) 0.0255(3) Uani 1 1 d .
H23 H 0.1038 0.3702 0.3976 0.031 Uiso 1 1 calc R
C24 C 0.01425(15) 0.52820(15) 0.37003(12) 0.0255(3) Uani 1 1 d .
H24 H -0.0638 0.5050 0.3943 0.031 Uiso 1 1 calc R
C25 C 0.02862(15) 0.64236(14) 0.33312(12) 0.0246(3) Uani 1 1 d .
H25 H -0.0395 0.6972 0.3324 0.030 Uiso 1 1 calc R
C26 C 0.14206(15) 0.67671(13) 0.29732(12) 0.0221(3) Uani 1 1 d .
H26 H 0.1519 0.7551 0.2724 0.027 Uiso 1 1 calc R
C31 C 0.28661(14) 0.67151(13) 0.10231(11) 0.0188(2) Uani 1 1 d .
C32 C 0.29561(15) 0.78756(14) 0.06664(12) 0.0234(3) Uani 1 1 d .
H32 H 0.3592 0.8505 0.1136 0.028 Uiso 1 1 calc R
C33 C 0.21148(17) 0.81148(16) -0.03792(13) 0.0292(3) Uani 1 1 d .
H33 H 0.2168 0.8909 -0.0616 0.035 Uiso 1 1 calc R
C34 C 0.12002(16) 0.71937(17) -0.10728(12) 0.0304(3) Uani 1 1 d .
H34 H 0.0634 0.7357 -0.1787 0.036 Uiso 1 1 calc R
C35 C 0.11097(16) 0.60307(16) -0.07252(12) 0.0282(3) Uani 1 1 d .
H35 H 0.0493 0.5398 -0.1206 0.034 Uiso 1 1 calc R
C36 C 0.19229(15) 0.57957(14) 0.03256(12) 0.0234(3) Uani 1 1 d .
H36 H 0.1838 0.5008 0.0571 0.028 Uiso 1 1 calc R
C41 C 0.48239(14) 0.51562(12) 0.24402(11) 0.0186(2) Uani 1 1 d .
C42 C 0.56771(15) 0.48729(14) 0.34705(12) 0.0230(3) Uani 1 1 d .
H42 H 0.5719 0.5357 0.4119 0.028 Uiso 1 1 calc R
C43 C 0.64639(16) 0.38878(15) 0.35508(13) 0.0266(3) Uani 1 1 d .
H43 H 0.7028 0.3687 0.4253 0.032 Uiso 1 1 calc R
C44 C 0.64196(17) 0.31972(15) 0.25956(14) 0.0292(3) Uani 1 1 d .
H44 H 0.6957 0.2524 0.2647 0.035 Uiso 1 1 calc R
C45 C 0.55980(17) 0.34836(15) 0.15716(13) 0.0289(3) Uani 1 1 d .
H45 H 0.5585 0.3014 0.0923 0.035 Uiso 1 1 calc R
C46 C 0.47892(15) 0.44585(13) 0.14879(12) 0.0224(3) Uani 1 1 d .
H46 H 0.4216 0.4647 0.0785 0.027 Uiso 1 1 calc R
S S 0.24948(4) 0.11091(3) 0.30995(3) 0.02176(7) Uani 1 1 d .
O3 O 0.12637(12) 0.15340(11) 0.32822(9) 0.0305(2) Uani 1 1 d .
O4 O 0.25930(14) -0.01740(11) 0.31721(10) 0.0354(3) Uani 1 1 d .
O5 O 0.37772(12) 0.18875(12) 0.36316(10) 0.0370(3) Uani 1 1 d .
C99 C 0.22339(16) 0.12851(14) 0.16397(12) 0.0246(3) Uani 1 1 d .
F1 F 0.10687(11) 0.06224(10) 0.10042(8) 0.0376(2) Uani 1 1 d .
F2 F 0.21053(11) 0.24414(9) 0.14211(8) 0.0326(2) Uani 1 1 d .
F3 F 0.33047(11) 0.09406(10) 0.13348(9) 0.0393(2) 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'
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'
S S 0.1246 0.1234 '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_publ_flag
C11 Pd O1 81.91(5) y
C11 Pd O2 170.39(5) y
O1 Pd O2 88.79(4) y
C11 Pd P 95.32(4) y
O1 Pd P 177.22(3) y
O2 Pd P 93.98(3) y
C41 P C31 109.74(6) y
C41 P C21 105.27(6) y
C31 P C21 101.82(6) y
C41 P Pd 111.99(5) y
C31 P Pd 113.75(5) y
C21 P Pd 113.51(4) y
C17 O1 Pd 112.75(9) y
C16 C11 C12 116.65(12) y
C16 C11 Pd 132.22(11) y
C12 C11 Pd 111.12(9) y
C13 C12 C11 121.71(12) y
C13 C12 C17 122.10(13) y
C11 C12 C17 116.19(12) y
C14 C13 C12 119.71(13) y
C15 C14 C13 119.21(13) y
C14 C15 C16 121.28(13) y
C15 C16 C11 121.46(13) y
O1 C17 C12 117.99(12) y
O1 C17 C18 117.29(12) y
C12 C17 C18 124.72(12) y
C22 C21 C26 119.77(13) ?
C22 C21 P 123.30(10) ?
C26 C21 P 116.89(10) ?
C21 C22 C23 119.79(13) ?
C24 C23 C22 120.20(14) ?
C23 C24 C25 120.12(14) ?
C26 C25 C24 120.23(14) ?
C25 C26 C21 119.90(14) ?
C32 C31 C36 119.45(12) ?
C32 C31 P 119.43(10) ?
C36 C31 P 120.80(11) ?
C31 C32 C33 120.16(14) ?
C34 C33 C32 120.03(15) ?
C33 C34 C35 120.16(14) ?
C36 C35 C34 119.96(15) ?
C35 C36 C31 120.21(14) ?
C46 C41 C42 119.57(13) ?
C46 C41 P 123.85(11) ?
C42 C41 P 116.57(10) ?
C43 C42 C41 120.41(14) ?
C42 C43 C44 119.51(14) ?
C45 C44 C43 120.47(14) ?
C44 C45 C46 120.25(14) ?
C45 C46 C41 119.77(13) ?
O3 S O4 114.95(8) ?
O3 S O5 114.27(8) ?
O4 S O5 115.86(8) ?
O3 S C99 104.00(7) ?
O4 S C99 102.94(7) ?
O5 S C99 102.34(7) ?
F3 C99 F1 107.70(13) ?
F3 C99 F2 107.67(12) ?
F1 C99 F2 107.63(12) ?
F3 C99 S 111.68(10) ?
F1 C99 S 111.07(10) ?
F2 C99 S 110.90(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Pd C11 1.9838(13) y
Pd O1 2.1045(10) y
Pd O2 2.1373(10) y
Pd P 2.2268(4) y
P C41 1.8163(14) y
P C31 1.8171(13) y
P C21 1.8256(14) y
O1 C17 1.2521(17) y
C11 C16 1.3947(19) y
C11 C12 1.4232(19) y
C12 C13 1.4047(19) y
C12 C17 1.4601(19) y
C13 C14 1.388(2) y
C14 C15 1.387(2) y
C15 C16 1.392(2) y
C17 C18 1.498(2) y
C21 C22 1.3902(19) ?
C21 C26 1.4032(19) ?
C22 C23 1.397(2) ?
C23 C24 1.386(2) ?
C24 C25 1.387(2) ?
C25 C26 1.387(2) ?
C31 C32 1.394(2) ?
C31 C36 1.399(2) ?
C32 C33 1.395(2) ?
C33 C34 1.387(2) ?
C34 C35 1.392(2) ?
C35 C36 1.390(2) ?
C41 C46 1.3949(19) ?
C41 C42 1.3991(19) ?
C42 C43 1.390(2) ?
C43 C44 1.391(2) ?
C44 C45 1.383(2) ?
C45 C46 1.394(2) ?
S O3 1.4375(12) ?
S O4 1.4410(12) ?
S O5 1.4442(12) ?
S C99 1.8238(15) ?
C99 F3 1.3279(18) ?
C99 F1 1.3346(17) ?
C99 F2 1.3355(18) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H01 O5 0.785(16) 1.897(17) 2.6643(16) 165(2) 2_666
O2 H02 O4 0.781(16) 2.110(17) 2.7521(16) 139.7(19) 1_565
O2 H02 O1 0.781(16) 2.394(18) 2.9674(14) 131.2(18) 2_676
C13 H13 O3 0.95 2.36 3.3097(19) 173.3 1_665
C18 H18B O3 0.98 2.51 3.4874(19) 172.3 1_665
C23 H23 O3 0.95 2.57 3.305(2) 134.5 .
C26 H26 O4 0.95 2.62 3.4712(19) 148.7 1_565
