#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:41:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178529 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/34/4063453.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_4063453
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            'C19 H29 F3 N2 O8 Pd S'
_chemical_formula_weight         608.90
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     Patterson
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.045(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.6847(12)
_cell_length_b                   10.1913(8)
_cell_length_c                   15.3249(12)
_cell_measurement_reflns_used    6411
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      2.3
_cell_volume                     2443.5(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            42892
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.9529
_exptl_absorpt_correction_T_min  0.8453
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   XPREP
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment
'OH free; C4, C6 as rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         7137
_refine_ls_number_restraints     168
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0298P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0627
_reflns_number_gt                5381
_reflns_number_total             7137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900957s_si_002.cif
_cod_data_source_block           jaya
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4063453
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd 0.231348(9) 0.169863(13) 0.525970(9) 0.01355(4) Uani 1 1 d . A .
O1 O 0.31160(8) 0.26514(13) 0.44539(8) 0.0169(3) Uani 1 1 d . . .
O2 O 0.44372(9) 0.34690(13) 0.45081(9) 0.0213(3) Uani 1 1 d . . .
O3 O 0.38919(9) -0.04384(13) 0.45630(9) 0.0216(3) Uani 1 1 d . . .
O4 O 0.31929(9) -0.14047(12) 0.56255(9) 0.0220(3) Uani 1 1 d . . .
O5 O 0.31107(9) 0.38509(15) 0.62633(10) 0.0239(3) Uani 1 1 d . . .
H05 H 0.2795(17) 0.415(3) 0.6546(17) 0.039(8) Uiso 1 1 d . . .
C1 C 0.34384(12) 0.08684(17) 0.57466(12) 0.0147(4) Uani 1 1 d . . .
H1 H 0.3423 0.0677 0.6385 0.018 Uiso 1 1 calc R . .
C2 C 0.41458(12) 0.18780(17) 0.55814(12) 0.0142(4) Uani 1 1 d . . .
H2 H 0.4658 0.1374 0.5419 0.017 Uiso 1 1 calc R . .
C3 C 0.35428(12) -0.03556(17) 0.52418(12) 0.0156(4) Uani 1 1 d . . .
C4 C 0.32595(15) -0.26495(19) 0.51848(15) 0.0305(5) Uani 1 1 d . . .
H4A H 0.3050 -0.2556 0.4570 0.037 Uiso 1 1 calc R . .
H4B H 0.2915 -0.3307 0.5467 0.037 Uiso 1 1 calc R . .
H4C H 0.3858 -0.2931 0.5218 0.037 Uiso 1 1 calc R . .
C5 C 0.38495(12) 0.27001(17) 0.48033(12) 0.0154(4) Uani 1 1 d . . .
C6 C 0.41818(14) 0.4282(2) 0.37540(14) 0.0277(5) Uani 1 1 d . . .
H6A H 0.4028 0.3720 0.3248 0.033 Uiso 1 1 calc R . .
H6B H 0.4657 0.4856 0.3621 0.033 Uiso 1 1 calc R . .
H6C H 0.3688 0.4819 0.3884 0.033 Uiso 1 1 calc R . .
C11 C 0.44128(12) 0.26740(17) 0.63955(11) 0.0145(4) Uani 1 1 d . . .
C12 C 0.38528(12) 0.35701(17) 0.67526(13) 0.0168(4) Uani 1 1 d . . .
C13 C 0.40614(13) 0.41483(19) 0.75610(13) 0.0200(4) Uani 1 1 d . . .
H13 H 0.3668 0.4722 0.7811 0.024 Uiso 1 1 calc R . .
C14 C 0.48450(13) 0.38847(19) 0.79997(13) 0.0205(4) Uani 1 1 d . . .
H14 H 0.4986 0.4276 0.8554 0.025 Uiso 1 1 calc R . .
C15 C 0.54275(13) 0.30507(18) 0.76357(13) 0.0201(4) Uani 1 1 d . . .
H15 H 0.5973 0.2896 0.7928 0.024 Uiso 1 1 calc R . .
C16 C 0.52001(12) 0.24466(18) 0.68388(12) 0.0171(4) Uani 1 1 d . . .
H16 H 0.5593 0.1866 0.6593 0.021 Uiso 1 1 calc R . .
N1 N 0.12030(11) 0.26757(17) 0.47026(11) 0.0212(4) Uani 1 1 d U . .
N2 N 0.15057(11) 0.09108(16) 0.61147(11) 0.0223(4) Uani 1 1 d U . .
C21 C 0.0486(8) 0.2207(7) 0.5284(7) 0.0235(16) Uani 0.517(5) 1 d PU A 1
H21A H 0.0041 0.2894 0.5296 0.028 Uiso 0.517(5) 1 calc PR A 1
H21B H 0.0217 0.1404 0.5028 0.028 Uiso 0.517(5) 1 calc PR A 1
C22 C 0.0837(3) 0.1928(4) 0.6195(3) 0.0236(11) Uani 0.517(5) 1 d PU A 1
H22A H 0.1087 0.2731 0.6471 0.028 Uiso 0.517(5) 1 calc PR A 1
H22B H 0.0382 0.1600 0.6554 0.028 Uiso 0.517(5) 1 calc PR A 1
C23 C 0.1311(9) 0.4039(12) 0.4743(6) 0.0227(17) Uani 0.517(5) 1 d PU A 1
H23A H 0.1469 0.4301 0.5348 0.027 Uiso 0.517(5) 1 calc PR A 1
H23B H 0.0775 0.4471 0.4539 0.027 Uiso 0.517(5) 1 calc PR A 1
H23C H 0.1764 0.4299 0.4370 0.027 Uiso 0.517(5) 1 calc PR A 1
C24 C 0.0916(11) 0.210(2) 0.3807(13) 0.018(2) Uani 0.517(5) 1 d PU A 1
H24A H 0.0867 0.1147 0.3854 0.022 Uiso 0.517(5) 1 calc PR A 1
H24B H 0.1338 0.2320 0.3387 0.022 Uiso 0.517(5) 1 calc PR A 1
H24C H 0.0360 0.2474 0.3606 0.022 Uiso 0.517(5) 1 calc PR A 1
C25 C 0.1207(4) -0.0381(7) 0.5914(4) 0.0242(12) Uani 0.517(5) 1 d PU A 1
H25A H 0.1696 -0.0971 0.5876 0.029 Uiso 0.517(5) 1 calc PR A 1
H25B H 0.0866 -0.0374 0.5353 0.029 Uiso 0.517(5) 1 calc PR A 1
H25C H 0.0853 -0.0687 0.6375 0.029 Uiso 0.517(5) 1 calc PR A 1
C26 C 0.1935(3) 0.0833(5) 0.7094(3) 0.0246(10) Uani 0.517(5) 1 d PU A 1
H26A H 0.2150 0.1701 0.7275 0.030 Uiso 0.517(5) 1 calc PR A 1
H26B H 0.2409 0.0206 0.7117 0.030 Uiso 0.517(5) 1 calc PR A 1
H26C H 0.1507 0.0544 0.7490 0.030 Uiso 0.517(5) 1 calc PR A 1
C21' C 0.0544(8) 0.2606(7) 0.5299(7) 0.0185(15) Uani 0.483(5) 1 d PU A 2
H21C H -0.0022 0.2776 0.4993 0.022 Uiso 0.483(5) 1 calc PR A 2
H21D H 0.0644 0.3257 0.5775 0.022 Uiso 0.483(5) 1 calc PR A 2
C22' C 0.0586(3) 0.1231(5) 0.5660(3) 0.0242(12) Uani 0.483(5) 1 d PU A 2
H22C H 0.0451 0.0598 0.5180 0.029 Uiso 0.483(5) 1 calc PR A 2
H22D H 0.0151 0.1127 0.6094 0.029 Uiso 0.483(5) 1 calc PR A 2
C23' C 0.1365(10) 0.4172(13) 0.4508(7) 0.0226(18) Uani 0.483(5) 1 d PU A 2
H23D H 0.1808 0.4251 0.4091 0.027 Uiso 0.483(5) 1 calc PR A 2
H23E H 0.1555 0.4621 0.5054 0.027 Uiso 0.483(5) 1 calc PR A 2
H23F H 0.0835 0.4575 0.4261 0.027 Uiso 0.483(5) 1 calc PR A 2
C24' C 0.1068(13) 0.218(2) 0.3836(15) 0.024(3) Uani 0.483(5) 1 d PU A 2
H24D H 0.1589 0.2290 0.3528 0.029 Uiso 0.483(5) 1 calc PR A 2
H24E H 0.0597 0.2655 0.3525 0.029 Uiso 0.483(5) 1 calc PR A 2
H24F H 0.0924 0.1242 0.3859 0.029 Uiso 0.483(5) 1 calc PR A 2
C25' C 0.1589(3) 0.1463(5) 0.6927(3) 0.0251(11) Uani 0.483(5) 1 d PU A 2
H25D H 0.1591 0.2421 0.6872 0.030 Uiso 0.483(5) 1 calc PR A 2
H25E H 0.2127 0.1173 0.7231 0.030 Uiso 0.483(5) 1 calc PR A 2
H25F H 0.1109 0.1191 0.7262 0.030 Uiso 0.483(5) 1 calc PR A 2
C26' C 0.1488(4) -0.0574(7) 0.6141(5) 0.0210(12) Uani 0.483(5) 1 d PU A 2
H26D H 0.1426 -0.0918 0.5543 0.025 Uiso 0.483(5) 1 calc PR A 2
H26E H 0.1004 -0.0866 0.6463 0.025 Uiso 0.483(5) 1 calc PR A 2
H26F H 0.2022 -0.0899 0.6435 0.025 Uiso 0.483(5) 1 calc PR A 2
S S 0.12144(3) 0.57509(5) 0.71333(3) 0.02102(11) Uani 1 1 d . . .
O6 O 0.03966(9) 0.53578(15) 0.74041(10) 0.0314(4) Uani 1 1 d . . .
O7 O 0.18541(10) 0.47291(15) 0.72157(10) 0.0340(4) Uani 1 1 d . . .
O8 O 0.12104(11) 0.65012(14) 0.63402(10) 0.0342(4) Uani 1 1 d . . .
C99 C 0.15928(17) 0.6907(2) 0.79816(15) 0.0348(6) Uani 1 1 d . . .
F1 F 0.23621(10) 0.73689(16) 0.78417(10) 0.0569(5) Uani 1 1 d . . .
F2 F 0.16408(11) 0.63358(15) 0.87728(9) 0.0515(4) Uani 1 1 d . . .
F3 F 0.10691(12) 0.79291(14) 0.80179(10) 0.0548(5) 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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0900
0.00 0.00 -1.00 0.0950
1.00 0.00 0.00 0.0230
-1.00 0.00 0.00 0.0320
1.00 -1.00 0.00 0.0720
-1.00 1.00 0.00 0.1100
-1.00 -1.00 0.00 0.0840
1.00 1.00 0.00 0.0900
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
C1 Pd N2 99.24(7) . . ?
C1 Pd O1 82.33(6) . . ?
N2 Pd O1 174.88(6) . . ?
C1 Pd N1 175.41(7) . . ?
N2 Pd N1 85.10(7) . . ?
O1 Pd N1 93.21(6) . . ?
C5 O1 Pd 110.34(11) . . ?
C5 O2 C6 116.91(16) . . ?
C3 O4 C4 116.44(16) . . ?
C3 C1 C2 111.54(15) . . ?
C3 C1 Pd 106.34(12) . . ?
C2 C1 Pd 105.95(12) . . ?
C5 C2 C11 113.88(14) . . ?
C5 C2 C1 108.37(15) . . ?
C11 C2 C1 112.29(14) . . ?
O3 C3 O4 122.61(17) . . ?
O3 C3 C1 125.41(17) . . ?
O4 C3 C1 111.98(15) . . ?
O1 C5 O2 121.94(17) . . ?
O1 C5 C2 123.21(16) . . ?
O2 C5 C2 114.84(17) . . ?
C16 C11 C12 118.54(16) . . ?
C16 C11 C2 119.78(16) . . ?
C12 C11 C2 121.50(17) . . ?
O5 C12 C13 122.47(17) . . ?
O5 C12 C11 116.96(16) . . ?
C13 C12 C11 120.57(18) . . ?
C14 C13 C12 119.70(18) . . ?
C13 C14 C15 120.57(18) . . ?
C16 C15 C14 119.13(19) . . ?
C11 C16 C15 121.36(18) . . ?
C23 N1 C24' 113.9(11) . . ?
C23 N1 C21' 96.4(5) . . ?
C24' N1 C21' 120.8(9) . . ?
C23 N1 C24 116.4(9) . . ?
C24' N1 C24 8.8(15) . . ?
C21' N1 C24 112.0(8) . . ?
C23 N1 C21 111.6(6) . . ?
C24' N1 C21 111.0(10) . . ?
C21' N1 C21 15.2(5) . . ?
C24 N1 C21 102.6(8) . . ?
C23 N1 C23' 13.8(7) . . ?
C24' N1 C23' 100.6(11) . . ?
C21' N1 C23' 107.6(6) . . ?
C24 N1 C23' 103.9(10) . . ?
C21 N1 C23' 122.5(6) . . ?
C23 N1 Pd 110.7(6) . . ?
C24' N1 Pd 105.7(9) . . ?
C21' N1 Pd 109.1(5) . . ?
C24 N1 Pd 111.2(7) . . ?
C21 N1 Pd 103.3(4) . . ?
C23' N1 Pd 112.9(6) . . ?
C25' N2 C25 125.9(4) . . ?
C25' N2 C22 70.1(3) . . ?
C25 N2 C22 116.1(3) . . ?
C25' N2 C26' 112.8(3) . . ?
C25 N2 C26' 22.4(2) . . ?
C22 N2 C26' 132.9(3) . . ?
C25' N2 C22' 109.9(3) . . ?
C25 N2 C22' 79.7(3) . . ?
C22 N2 C22' 43.1(2) . . ?
C26' N2 C22' 101.5(3) . . ?
C25' N2 C26 32.7(2) . . ?
C25 N2 C26 105.4(3) . . ?
C22 N2 C26 102.1(3) . . ?
C26' N2 C26 86.1(3) . . ?
C22' N2 C26 136.7(3) . . ?
C25' N2 Pd 113.5(2) . . ?
C25 N2 Pd 115.7(3) . . ?
C22 N2 Pd 104.54(17) . . ?
C26' N2 Pd 115.0(3) . . ?
C22' N2 Pd 102.84(17) . . ?
C26 N2 Pd 112.37(18) . . ?
C22 C21 N1 111.1(8) . . ?
N2 C22 C21 105.8(5) . . ?
N1 C21' C22' 105.5(7) . . ?
C21' C22' N2 111.5(5) . . ?
O6 S O8 116.33(10) . . ?
O6 S O7 113.79(9) . . ?
O8 S O7 114.79(9) . . ?
O6 S C99 103.14(10) . . ?
O8 S C99 103.96(10) . . ?
O7 S C99 102.38(11) . . ?
F1 C99 F3 107.5(2) . . ?
F1 C99 F2 107.8(2) . . ?
F3 C99 F2 107.3(2) . . ?
F1 C99 S 111.60(16) . . ?
F3 C99 S 111.41(18) . . ?
F2 C99 S 110.99(16) . . ?
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 C1 2.0494(19) . ?
Pd N2 2.0496(16) . ?
Pd O1 2.0668(12) . ?
Pd N1 2.1318(17) . ?
O1 C5 1.235(2) . ?
O2 C5 1.314(2) . ?
O2 C6 1.455(2) . ?
O3 C3 1.212(2) . ?
O4 C3 1.355(2) . ?
O4 C4 1.445(2) . ?
O5 C12 1.370(2) . ?
C1 C3 1.483(2) . ?
C1 C2 1.547(2) . ?
C2 C5 1.504(3) . ?
C2 C11 1.522(2) . ?
C11 C16 1.386(3) . ?
C11 C12 1.404(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.392(3) . ?
N1 C23 1.400(12) . ?
N1 C24' 1.42(2) . ?
N1 C21' 1.430(12) . ?
N1 C24 1.530(18) . ?
N1 C21 1.558(10) . ?
N1 C23' 1.578(12) . ?
N2 C25' 1.364(5) . ?
N2 C25 1.424(7) . ?
N2 C22 1.486(4) . ?
N2 C26' 1.514(7) . ?
N2 C22' 1.591(5) . ?
N2 C26 1.603(5) . ?
C21 C22 1.491(12) . ?
C21' C22' 1.506(8) . ?
S O6 1.4329(15) . ?
S O8 1.4357(15) . ?
S O7 1.4455(15) . ?
S C99 1.823(2) . ?
C99 F1 1.326(3) . ?
C99 F3 1.330(3) . ?
C99 F2 1.342(3) . ?
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
O5 H05 O7 0.75(3) 1.95(3) 2.687(2) 171(3) .
C2 H2 O3 1.00 2.46 3.431(2) 162.4 3_656
C16 H16 O3 0.95 2.47 3.356(2) 154.7 3_656
C14 H14 O3 0.95 2.67 3.315(2) 125.8 4_566
C15 H15 O4 0.95 2.59 3.358(2) 137.8 2_656
