#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:47:42 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178701 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/12/4081212.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_4081212
loop_
_publ_author_name
'Gioria, Estefanía'
'Martínez-Ilarduya, Jesús M.'
'García-Cuadrado, Domingo'
'Miguel, Jesús A.'
'Genov, Miroslav'
'Espinet, Pablo'
_publ_section_title
;
 Phosphines with Tethered Electron-Withdrawing Olefins as Ligands for
 Efficient Pd-Catalyzed Aryl-Alkyl Coupling
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              4255
_journal_paper_doi               10.1021/om4004303
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C54 H34 Cl2 F8 O2 P2 Pd'
_chemical_formula_weight         1106.05
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.310(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.0505(2)
_cell_length_b                   19.4514(3)
_cell_length_c                   11.6614(2)
_cell_measurement_reflns_used    5891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6772
_cell_measurement_theta_min      2.0898
_cell_volume                     2393.06(7)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.51 (release 27-10-2009 CrysAlis171 .NET)
(compiled Oct 27 2009,12:04:35)  
;
_computing_data_collection
; 
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.51 (release 27-10-2009 CrysAlis171 .NET)
(compiled Oct 27 2009,12:04:35)
;
_computing_data_reduction
; 
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.51 (release 27-10-2009 CrysAlis171 .NET)
(compiled Oct 27 2009,12:04:35)  
;
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4757
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details
;
  1 omega   64.00  116.00   1.0000   27.3300
omega____ theta____ kappa____ phi______ frames
    -       21.5439  179.0000 -180.0000 52

  2 omega  -74.00  107.00   1.0000   27.3300
omega____ theta____ kappa____ phi______ frames
    -       21.5439    0.0000  150.0000 181
;
_diffrn_measurement_device_type  'SuperNova (Mo) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0264986000
_diffrn_orient_matrix_UB_12      -0.0198735000
_diffrn_orient_matrix_UB_13      -0.0375224000
_diffrn_orient_matrix_UB_21      0.0542345000
_diffrn_orient_matrix_UB_22      -0.0066080000
_diffrn_orient_matrix_UB_23      0.0495462000
_diffrn_orient_matrix_UB_31      -0.0296135000
_diffrn_orient_matrix_UB_32      -0.0298455000
_diffrn_orient_matrix_UB_33      0.0140659000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10588
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.4758
_exptl_crystal_size_mid          0.3575
_exptl_crystal_size_min          0.1499
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0240P)²+1.3387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                4247
_reflns_number_total             5420
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4004303_si_002.cif
_cod_data_source_block           13
_cod_original_cell_volume        2393.07(8)
_cod_database_code               4081212
#BEGIN Tags that were not found in dictionaries:
_cell_oxdiff_length_a            11.0513(5)
_cell_oxdiff_length_b            19.4539(6)
_cell_oxdiff_length_c            11.6604(5)
_cell_oxdiff_angle_alpha         89.970(3)
_cell_oxdiff_angle_beta          107.331(4)
_cell_oxdiff_angle_gamma         89.983(3)
_cell_oxdiff_volume              2393.07(16)
_cell_oxdiff_measurement_reflns_used 5891
#END Tags that were not found in dictionaries
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
Pd1 Pd 0.5000 0.0000 1.0000 0.03577(9) Uani 1 2 d S
Cl1 Cl 0.32890(8) 0.07247(5) 0.95069(8) 0.0654(3) Uani 1 1 d .
P1 P 0.51827(7) 0.01880(3) 0.80912(6) 0.03667(17) Uani 1 1 d .
C1 C 0.6614(3) -0.01939(14) 0.7873(3) 0.0423(7) Uani 1 1 d .
C2 C 0.6621(3) -0.07662(15) 0.7192(3) 0.0536(8) Uani 1 1 d .
C3 C 0.7724(4) -0.10330(18) 0.7045(3) 0.0696(11) Uani 1 1 d .
C4 C 0.8834(4) -0.0715(2) 0.7569(4) 0.0710(11) Uani 1 1 d .
C5 C 0.8869(3) -0.01396(19) 0.8244(3) 0.0616(9) Uani 1 1 d .
F2 F 0.5556(2) -0.10977(10) 0.6620(2) 0.0817(7) Uani 1 1 d .
F3 F 0.7667(3) -0.15855(12) 0.6359(2) 0.1087(9) Uani 1 1 d .
F4 F 0.9904(2) -0.09595(14) 0.7411(2) 0.1089(9) Uani 1 1 d .
F5 F 1.00056(19) 0.01534(13) 0.8739(2) 0.0887(7) Uani 1 1 d .
C6 C 0.7789(3) 0.01295(15) 0.8445(3) 0.0482(7) Uani 1 1 d .
C7 C 0.7871(3) 0.07157(16) 0.9252(3) 0.0503(7) Uani 1 1 d .
H7 H 0.7304 0.0711 0.9703 0.060 Uiso 1 1 calc R
C8 C 0.8637(3) 0.12475(19) 0.9425(3) 0.0654(9) Uani 1 1 d .
H8 H 0.9213 0.1284 0.8987 0.079 Uiso 1 1 calc R
C9 C 0.8598(3) 0.17883(18) 1.0301(3) 0.0606(9) Uani 1 1 d .
O1 O 0.7677(2) 0.18355(13) 1.0659(3) 0.0784(8) Uani 1 1 d .
C10 C 0.9706(3) 0.22568(19) 1.0753(3) 0.0646(10) Uani 1 1 d .
C11 C 1.0812(4) 0.2170(2) 1.0459(4) 0.0919(14) Uani 1 1 d .
H11 H 1.0885 0.1818 0.9943 0.110 Uiso 1 1 calc R
C12 C 1.1823(5) 0.2616(3) 1.0945(5) 0.1172(19) Uani 1 1 d .
H12 H 1.2574 0.2567 1.0748 0.141 Uiso 1 1 calc R
C13 C 1.1708(6) 0.3123(3) 1.1708(5) 0.114(2) Uani 1 1 d .
H13 H 1.2386 0.3419 1.2031 0.137 Uiso 1 1 calc R
C14 C 1.0631(5) 0.3204(2) 1.2002(4) 0.1025(16) Uani 1 1 d .
H14 H 1.0566 0.3553 1.2525 0.123 Uiso 1 1 calc R
C15 C 0.9627(4) 0.2771(2) 1.1531(4) 0.0818(12) Uani 1 1 d .
H15 H 0.8885 0.2827 1.1741 0.098 Uiso 1 1 calc R
C16 C 0.5308(3) 0.10497(13) 0.7536(3) 0.0413(6) Uani 1 1 d .
C17 C 0.5651(3) 0.11326(15) 0.6497(3) 0.0545(8) Uani 1 1 d .
H17 H 0.5776 0.0748 0.6074 0.065 Uiso 1 1 calc R
C18 C 0.5808(4) 0.17753(18) 0.6084(3) 0.0703(10) Uani 1 1 d .
H18 H 0.6039 0.1826 0.5385 0.084 Uiso 1 1 calc R
C19 C 0.5625(4) 0.23381(18) 0.6703(4) 0.0795(12) Uani 1 1 d .
H19 H 0.5725 0.2775 0.6420 0.095 Uiso 1 1 calc R
C20 C 0.5296(4) 0.22674(17) 0.7733(4) 0.0756(11) Uani 1 1 d .
H20 H 0.5180 0.2656 0.8152 0.091 Uiso 1 1 calc R
C21 C 0.5133(3) 0.16239(14) 0.8160(3) 0.0548(8) Uani 1 1 d .
H21 H 0.4907 0.1578 0.8863 0.066 Uiso 1 1 calc R
C22 C 0.3792(3) -0.02045(14) 0.7054(3) 0.0443(7) Uani 1 1 d .
C23 C 0.3106(4) 0.00953(19) 0.6004(3) 0.0717(11) Uani 1 1 d .
H23 H 0.3369 0.0510 0.5762 0.086 Uiso 1 1 calc R
C24 C 0.2020(4) -0.0222(3) 0.5302(4) 0.1021(16) Uani 1 1 d .
H24 H 0.1549 -0.0015 0.4590 0.123 Uiso 1 1 calc R
C25 C 0.1628(4) -0.0832(2) 0.5637(4) 0.0848(13) Uani 1 1 d .
H25 H 0.0905 -0.1044 0.5146 0.102 Uiso 1 1 calc R
C26 C 0.2287(4) -0.11272(18) 0.6678(4) 0.0681(10) Uani 1 1 d .
H26 H 0.2021 -0.1545 0.6906 0.082 Uiso 1 1 calc R
C27 C 0.3354(3) -0.08125(15) 0.7406(3) 0.0560(8) Uani 1 1 d .
H27 H 0.3784 -0.1009 0.8141 0.067 Uiso 1 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'
Cl Cl 0.1484 0.1585 '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'
P P 0.1023 0.0942 '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
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3 -7 16 0.0791 -3.0000 -7.0000 16.0000 -0.5407 0.6763 0.5228
0 -27 3 0.1307 0.0000 -27.0000 3.0000 0.4240 0.3271 0.8480
-15 -2 6 0.1400 -15.0000 -2.0000 6.0000 -0.5829 -0.5030 0.5883
15 2 -6 0.1664 15.0000 2.0000 -6.0000 0.5829 0.5030 -0.5883
8 22 -6 0.1366 8.0000 22.0000 -6.0000 -0.0001 -0.0088 -0.9779
3 6 -16 0.0650 3.0000 6.0000 -16.0000 0.5606 -0.6697 -0.4930
-1 -11 -14 0.0690 -1.0000 -11.0000 -14.0000 0.7174 -0.6752 0.1610
-1 14 14 0.1604 -1.0000 14.0000 14.0000 -0.8300 0.5469 -0.1913
-1 -13 14 0.0755 -1.0000 -13.0000 14.0000 -0.2935 0.7253 0.6145
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
Cl1 Pd1 Cl1 180.0 . 3_657
Cl1 Pd1 P1 87.89(3) . .
Cl1 Pd1 P1 92.11(3) 3_657 .
Cl1 Pd1 P1 92.11(3) . 3_657
Cl1 Pd1 P1 87.89(3) 3_657 3_657
P1 Pd1 P1 180.0 . 3_657
C22 P1 C16 106.83(13) . .
C22 P1 C1 109.36(14) . .
C16 P1 C1 99.43(13) . .
C22 P1 Pd1 105.91(10) . .
C16 P1 Pd1 121.62(10) . .
C1 P1 Pd1 113.20(9) . .
C2 C1 C6 118.1(3) . .
C2 C1 P1 124.4(2) . .
C6 C1 P1 117.5(2) . .
F2 C2 C1 121.8(3) . .
F2 C2 C3 115.8(3) . .
C1 C2 C3 122.4(3) . .
F3 C3 C4 121.1(4) . .
F3 C3 C2 119.6(4) . .
C4 C3 C2 119.3(3) . .
F4 C4 C3 119.9(4) . .
F4 C4 C5 119.8(4) . .
C3 C4 C5 120.3(3) . .
F5 C5 C4 117.3(3) . .
F5 C5 C6 120.6(3) . .
C4 C5 C6 122.0(4) . .
C5 C6 C1 117.8(3) . .
C5 C6 C7 120.7(3) . .
C1 C6 C7 121.4(3) . .
C8 C7 C6 128.7(3) . .
C7 C8 C9 121.2(3) . .
O1 C9 C8 119.5(3) . .
O1 C9 C10 121.1(3) . .
C8 C9 C10 119.4(3) . .
C15 C10 C11 119.4(4) . .
C15 C10 C9 118.3(4) . .
C11 C10 C9 122.3(4) . .
C10 C11 C12 119.0(5) . .
C13 C12 C11 119.9(5) . .
C14 C13 C12 120.9(5) . .
C13 C14 C15 120.0(5) . .
C10 C15 C14 120.7(5) . .
C21 C16 C17 119.1(3) . .
C21 C16 P1 121.5(2) . .
C17 C16 P1 119.3(2) . .
C18 C17 C16 120.7(3) . .
C19 C18 C17 119.6(3) . .
C18 C19 C20 120.5(3) . .
C19 C20 C21 120.5(3) . .
C16 C21 C20 119.5(3) . .
C23 C22 C27 118.7(3) . .
C23 C22 P1 123.5(2) . .
C27 C22 P1 117.6(2) . .
C22 C23 C24 119.6(3) . .
C25 C24 C23 121.0(4) . .
C26 C25 C24 119.9(4) . .
C25 C26 C27 120.1(3) . .
C26 C27 C22 120.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 Cl1 2.2903(7) .
Pd1 Cl1 2.2903(7) 3_657
Pd1 P1 2.3231(7) .
Pd1 P1 2.3232(7) 3_657
P1 C22 1.817(3) .
P1 C16 1.817(3) .
P1 C1 1.833(3) .
C1 C2 1.369(4) .
C1 C6 1.418(4) .
C2 F2 1.334(4) .
C2 C3 1.381(5) .
C3 F3 1.330(4) .
C3 C4 1.347(6) .
C4 F4 1.337(4) .
C4 C5 1.363(5) .
C5 F5 1.343(4) .
C5 C6 1.386(4) .
C6 C7 1.464(4) .
C7 C8 1.314(4) .
C8 C9 1.476(5) .
C9 O1 1.212(4) .
C9 C10 1.491(5) .
C10 C15 1.370(5) .
C10 C11 1.376(5) .
C11 C12 1.395(6) .
C12 C13 1.360(7) .
C13 C14 1.342(7) .
C14 C15 1.371(6) .
C16 C21 1.378(4) .
C16 C17 1.382(4) .
C17 C18 1.369(4) .
C18 C19 1.359(5) .
C19 C20 1.362(5) .
C20 C21 1.378(4) .
C22 C23 1.365(4) .
C22 C27 1.386(4) .
C23 C24 1.381(5) .
C24 C25 1.359(5) .
C25 C26 1.345(5) .
C26 C27 1.374(4) .
