#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/34/4063454.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_4063454
loop_
_publ_author_name
'Vicente, José'
'Abad, José Antonio'
'López-Sáez, María-José'
'Jones, Peter G.'
_publ_section_title
;
 Carbopalladation of Maleate and Fumarate Esters and 1,1-Dimethylallene
 with Ortho-Substituted Aryl Palladium Complexes
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              409
_journal_paper_doi               10.1021/om900957s
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C27.5 H28 F3 N2 O8.5 Pd S'
_chemical_formula_weight         717.98
_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-97
_cell_angle_alpha                99.933(4)
_cell_angle_beta                 90.461(4)
_cell_angle_gamma                109.265(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3620(8)
_cell_length_b                   11.3529(11)
_cell_length_c                   14.6379(14)
_cell_measurement_reflns_used    5310
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2.3
_cell_volume                     1443.1(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 0.984
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω-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  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15210
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.683
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    'rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7290
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0347
_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)+(0.0283P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                5719
_reflns_number_total             7290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900957s_si_002.cif
_cod_data_source_block           nwell
_cod_original_formula_sum        'C27.50 H28 F3 N2 O8.50 Pd S'
_cod_database_code               4063454
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd 0.69258(2) 0.496824(18) 0.370491(13) 0.01724(6) Uani 1 1 d . . .
O1 O 0.85542(19) 0.42048(16) 0.18157(12) 0.0233(4) Uani 1 1 d . . .
O2 O 0.61560(19) 0.28276(16) 0.16399(12) 0.0235(4) Uani 1 1 d . . .
O3 O 0.99739(19) 0.76707(16) 0.25628(12) 0.0229(4) Uani 1 1 d . . .
O4 O 0.88137(18) 0.64376(16) 0.35525(11) 0.0206(4) Uani 1 1 d . . .
O5 O 0.4480(2) 0.64728(18) 0.16613(13) 0.0290(4) Uani 1 1 d . . .
C1 C 0.6514(3) 0.4940(2) 0.23211(16) 0.0181(5) Uani 1 1 d . . .
H1 H 0.5407 0.4676 0.2136 0.022 Uiso 1 1 calc R . .
C2 C 0.7400(3) 0.6287(2) 0.21549(16) 0.0187(5) Uani 1 1 d . . .
H2 H 0.6763 0.6815 0.2389 0.022 Uiso 1 1 calc R . .
C3 C 0.7199(3) 0.3989(2) 0.18993(16) 0.0193(5) Uani 1 1 d . . .
C4 C 0.6734(3) 0.1799(2) 0.12772(19) 0.0283(6) Uani 1 1 d . . .
H4A H 0.7603 0.1837 0.1684 0.034 Uiso 1 1 calc R . .
H4B H 0.7073 0.1869 0.0644 0.034 Uiso 1 1 calc R . .
C5 C 0.5449(4) 0.0574(3) 0.1256(2) 0.0407(8) Uani 1 1 d . . .
H5A H 0.5138 0.0509 0.1888 0.049 Uiso 1 1 calc R . .
H5B H 0.5783 -0.0142 0.1005 0.049 Uiso 1 1 calc R . .
H5C H 0.4590 0.0557 0.0861 0.049 Uiso 1 1 calc R . .
C6 C 0.8811(3) 0.6801(2) 0.27925(17) 0.0195(5) Uani 1 1 d . . .
C7 C 1.1307(3) 0.8264(3) 0.32411(19) 0.0279(6) Uani 1 1 d . . .
H7A H 1.1475 0.7624 0.3570 0.034 Uiso 1 1 calc R . .
H7B H 1.1153 0.8948 0.3706 0.034 Uiso 1 1 calc R . .
C8 C 1.2630(3) 0.8793(3) 0.2692(2) 0.0384(7) Uani 1 1 d . . .
H8A H 1.2809 0.8098 0.2265 0.046 Uiso 1 1 calc R . .
H8B H 1.3533 0.9250 0.3116 0.046 Uiso 1 1 calc R . .
H8C H 1.2415 0.9378 0.2335 0.046 Uiso 1 1 calc R . .
C11 C 0.7587(3) 0.6407(2) 0.11383(17) 0.0201(5) Uani 1 1 d . . .
C12 C 0.6485(3) 0.6658(2) 0.06148(17) 0.0236(6) Uani 1 1 d . . .
C13 C 0.6708(3) 0.6809(3) -0.03099(18) 0.0304(6) Uani 1 1 d . . .
H13 H 0.5980 0.7011 -0.0650 0.036 Uiso 1 1 calc R . .
C14 C 0.7960(3) 0.6669(3) -0.07308(18) 0.0329(7) Uani 1 1 d . . .
H14 H 0.8096 0.6770 -0.1359 0.039 Uiso 1 1 calc R . .
C15 C 0.9021(3) 0.6382(3) -0.02365(18) 0.0311(6) Uani 1 1 d . . .
H15 H 0.9879 0.6265 -0.0529 0.037 Uiso 1 1 calc R . .
C16 C 0.8839(3) 0.6263(2) 0.06889(18) 0.0265(6) Uani 1 1 d . . .
H16 H 0.9589 0.6079 0.1023 0.032 Uiso 1 1 calc R . .
C17 C 0.5044(3) 0.6769(3) 0.09650(19) 0.0304(6) Uani 1 1 d . . .
H17 H 0.4504 0.7114 0.0595 0.037 Uiso 1 1 calc R . .
N21 N 0.7445(2) 0.49481(19) 0.50805(14) 0.0199(4) Uani 1 1 d . . .
C22 C 0.6376(3) 0.4071(2) 0.54563(17) 0.0206(5) Uani 1 1 d . . .
C23 C 0.6582(3) 0.3915(3) 0.63681(17) 0.0264(6) Uani 1 1 d . . .
H23 H 0.5822 0.3304 0.6628 0.032 Uiso 1 1 calc R . .
C24 C 0.7910(3) 0.4662(3) 0.68839(19) 0.0317(7) Uani 1 1 d . . .
H24 H 0.8075 0.4564 0.7503 0.038 Uiso 1 1 calc R . .
C25 C 0.9002(3) 0.5554(3) 0.64987(18) 0.0303(6) Uani 1 1 d . . .
H25 H 0.9922 0.6073 0.6847 0.036 Uiso 1 1 calc R . .
C26 C 0.8725(3) 0.5676(3) 0.55908(18) 0.0250(6) Uani 1 1 d . . .
H26 H 0.9465 0.6294 0.5324 0.030 Uiso 1 1 calc R . .
N31 N 0.5064(2) 0.35676(19) 0.39438(14) 0.0190(4) Uani 1 1 d . . .
C32 C 0.5018(3) 0.3321(2) 0.48267(17) 0.0205(5) Uani 1 1 d . . .
C33 C 0.3772(3) 0.2428(2) 0.50943(18) 0.0256(6) Uani 1 1 d . . .
H33 H 0.3762 0.2263 0.5709 0.031 Uiso 1 1 calc R . .
C34 C 0.2536(3) 0.1773(3) 0.4463(2) 0.0300(6) Uani 1 1 d . . .
H34 H 0.1666 0.1165 0.4642 0.036 Uiso 1 1 calc R . .
C35 C 0.2595(3) 0.2019(2) 0.35742(19) 0.0271(6) Uani 1 1 d . . .
H35 H 0.1766 0.1578 0.3128 0.033 Uiso 1 1 calc R . .
C36 C 0.3866(3) 0.2911(2) 0.33369(18) 0.0233(6) Uani 1 1 d . . .
H36 H 0.3898 0.3069 0.2720 0.028 Uiso 1 1 calc R . .
S S -0.19051(8) 0.01351(7) 0.33681(5) 0.02865(16) Uani 1 1 d . . .
O6 O -0.1115(2) 0.1013(2) 0.27936(14) 0.0428(5) Uani 1 1 d . . .
O7 O -0.0947(2) -0.0119(2) 0.40187(15) 0.0438(6) Uani 1 1 d . . .
O8 O -0.3131(2) -0.0954(2) 0.29234(16) 0.0490(6) Uani 1 1 d . . .
C99 C -0.2865(3) 0.1046(3) 0.4110(2) 0.0309(6) Uani 1 1 d . . .
F1 F -0.3564(2) 0.04470(19) 0.47668(14) 0.0581(6) Uani 1 1 d . . .
F2 F -0.1915(2) 0.21618(17) 0.45464(13) 0.0527(5) Uani 1 1 d . . .
F3 F -0.3896(2) 0.13050(19) 0.36176(14) 0.0576(6) Uani 1 1 d . . .
C96 C 0.0456(15) 0.0168(19) -0.0890(9) 0.056(4) Uani 0.50 1 d PDU A -1
C97 C -0.0664(8) 0.0023(6) -0.0111(5) 0.0476(17) Uani 0.50 1 d PDU A -1
C98 C 0.0022(14) -0.0153(16) 0.0807(8) 0.046(3) Uani 0.50 1 d PDU A -1
O99 O -0.1911(7) 0.0097(6) -0.0182(5) 0.096(2) Uani 0.50 1 d PDU A -1
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N31 Pd O4 176.25(7) . . ?
N31 Pd C1 100.99(9) . . ?
O4 Pd C1 82.31(8) . . ?
N31 Pd N21 80.14(8) . . ?
O4 Pd N21 96.67(7) . . ?
C1 Pd N21 176.46(9) . . ?
C3 O2 C4 116.28(19) . . ?
C6 O3 C7 118.12(19) . . ?
C6 O4 Pd 114.18(16) . . ?
C3 C1 C2 112.5(2) . . ?
C3 C1 Pd 100.14(15) . . ?
C2 C1 Pd 106.03(15) . . ?
C6 C2 C11 116.8(2) . . ?
C6 C2 C1 107.86(19) . . ?
C11 C2 C1 115.14(19) . . ?
O1 C3 O2 123.0(2) . . ?
O1 C3 C1 124.9(2) . . ?
O2 C3 C1 112.1(2) . . ?
O2 C4 C5 106.8(2) . . ?
O4 C6 O3 121.7(2) . . ?
O4 C6 C2 119.5(2) . . ?
O3 C6 C2 118.6(2) . . ?
O3 C7 C8 106.2(2) . . ?
C16 C11 C12 117.5(2) . . ?
C16 C11 C2 121.5(2) . . ?
C12 C11 C2 121.0(2) . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 C17 115.3(2) . . ?
C11 C12 C17 124.7(2) . . ?
C14 C13 C12 121.0(3) . . ?
C13 C14 C15 119.5(2) . . ?
C14 C15 C16 120.2(3) . . ?
C15 C16 C11 121.7(3) . . ?
O5 C17 C12 127.6(3) . . ?
C26 N21 C22 119.5(2) . . ?
C26 N21 Pd 126.12(17) . . ?
C22 N21 Pd 114.35(16) . . ?
N21 C22 C23 121.1(2) . . ?
N21 C22 C32 114.6(2) . . ?
C23 C22 C32 124.2(2) . . ?
C24 C23 C22 118.8(3) . . ?
C23 C24 C25 120.0(2) . . ?
C24 C25 C26 118.6(3) . . ?
N21 C26 C25 122.0(3) . . ?
C36 N31 C32 118.3(2) . . ?
C36 N31 Pd 126.32(17) . . ?
C32 N31 Pd 115.33(17) . . ?
N31 C32 C33 121.1(2) . . ?
N31 C32 C22 115.5(2) . . ?
C33 C32 C22 123.4(2) . . ?
C32 C33 C34 119.8(2) . . ?
C35 C34 C33 118.7(3) . . ?
C34 C35 C36 119.4(3) . . ?
N31 C36 C35 122.6(2) . . ?
O7 S O8 114.63(14) . . ?
O7 S O6 114.59(13) . . ?
O8 S O6 116.82(14) . . ?
O7 S C99 102.85(13) . . ?
O8 S C99 102.81(13) . . ?
O6 S C99 102.27(13) . . ?
F1 C99 F2 106.3(2) . . ?
F1 C99 F3 107.9(2) . . ?
F2 C99 F3 106.1(2) . . ?
F1 C99 S 112.4(2) . . ?
F2 C99 S 112.40(19) . . ?
F3 C99 S 111.3(2) . . ?
O99 C97 C96 124.2(8) . . ?
O99 C97 C98 122.8(8) . . ?
C96 C97 C98 112.9(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd N31 2.015(2) . ?
Pd O4 2.0361(17) . ?
Pd C1 2.052(2) . ?
Pd N21 2.073(2) . ?
O1 C3 1.221(3) . ?
O2 C3 1.344(3) . ?
O2 C4 1.465(3) . ?
O3 C6 1.298(3) . ?
O3 C7 1.480(3) . ?
O4 C6 1.252(3) . ?
O5 C17 1.200(3) . ?
C1 C3 1.481(3) . ?
C1 C2 1.542(3) . ?
C2 C6 1.497(3) . ?
C2 C11 1.524(3) . ?
C4 C5 1.504(4) . ?
C7 C8 1.495(4) . ?
C11 C16 1.391(3) . ?
C11 C12 1.411(3) . ?
C12 C13 1.402(3) . ?
C12 C17 1.482(4) . ?
C13 C14 1.371(4) . ?
C14 C15 1.378(4) . ?
C15 C16 1.391(4) . ?
N21 C26 1.340(3) . ?
N21 C22 1.355(3) . ?
C22 C23 1.397(3) . ?
C22 C32 1.479(4) . ?
C23 C24 1.380(4) . ?
C24 C25 1.382(4) . ?
C25 C26 1.391(3) . ?
N31 C36 1.344(3) . ?
N31 C32 1.367(3) . ?
C32 C33 1.380(3) . ?
C33 C34 1.387(4) . ?
C34 C35 1.376(4) . ?
C35 C36 1.376(3) . ?
S O7 1.430(2) . ?
S O8 1.430(2) . ?
S O6 1.435(2) . ?
S C99 1.816(3) . ?
C99 F1 1.325(3) . ?
C99 F2 1.331(3) . ?
C99 F3 1.336(3) . ?
C96 C97 1.548(10) . ?
C97 O99 1.203(8) . ?
C97 C98 1.555(12) . ?
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
C15 H15 O1 0.95 2.49 3.390(3) 158.2 2_765
C25 H25 O1 0.95 2.54 3.265(3) 133.6 2_766
C13 H13 O2 0.95 2.53 3.474(3) 170.9 2_665
C23 H23 O5 0.95 2.50 3.114(3) 122.4 2_666
C4 H4A O6 0.99 2.49 3.403(3) 153.6 1_655
C35 H35 O6 0.95 2.58 3.398(3) 144.4 .
C7 H7B O7 0.99 2.53 3.316(3) 135.8 1_665
C34 H34 O7 0.95 2.47 3.245(4) 138.9 .
C34 H34 O7 0.95 2.45 3.213(3) 137.2 2_556
C2 H2 O8 1.00 2.49 3.338(3) 142.7 1_665
C33 H33 O8 0.95 2.65 3.553(4) 158.6 2_556
