#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:47:42 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178701 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/12/4081211.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_4081211
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            'C32 H28 Cl4 F6 P2 Pd2'
_chemical_formula_weight         943.08
_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                92.188(8)
_cell_angle_beta                 99.326(13)
_cell_angle_gamma                104.527(9)
_cell_formula_units_Z            1
_cell_length_a                   7.4163(11)
_cell_length_b                   9.9658(6)
_cell_length_c                   12.6465(19)
_cell_measurement_reflns_used    1693
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5944
_cell_measurement_theta_min      2.1140
_cell_volume                     889.8(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details
;
  1 omega  -11.00  100.00   1.0000   16.2000
omega____ theta____ kappa____ phi______ frames
    -       21.7001   77.0000 -180.0000 111

  2 omega  -19.00   99.00   1.0000   16.2000
omega____ theta____ kappa____ phi______ frames
    -       21.7001   77.0000  -60.0000 118

  3 omega  -13.00  100.00   1.0000   16.2000
omega____ theta____ kappa____ phi______ frames
    -       21.7001   77.0000   60.0000 113

;
_diffrn_measurement_device_type  'SuperNova (Mo) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0456031000
_diffrn_orient_matrix_UB_12      -0.0054840000
_diffrn_orient_matrix_UB_13      0.0454018000
_diffrn_orient_matrix_UB_21      -0.0136038000
_diffrn_orient_matrix_UB_22      -0.0731617000
_diffrn_orient_matrix_UB_23      -0.0045236000
_diffrn_orient_matrix_UB_31      0.0883956000
_diffrn_orient_matrix_UB_32      0.0077507000
_diffrn_orient_matrix_UB_33      0.0342183000
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5795
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.66
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    1.455
_exptl_absorpt_correction_T_max  0.297
_exptl_absorpt_correction_T_min  0.185
_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            ORANGE
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2701
_exptl_crystal_size_mid          0.2004
_exptl_crystal_size_min          0.1603
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0546
_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)+(0.0663P)²+0.2173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1540
_reflns_number_gt                2470
_reflns_number_total             4014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4004303_si_002.cif
_cod_data_source_block           12
_cod_database_code               4081211
#BEGIN Tags that were not found in dictionaries:
_cell_oxdiff_length_a            7.4163(11)
_cell_oxdiff_length_b            9.9658(6)
_cell_oxdiff_length_c            12.6465(19)
_cell_oxdiff_angle_alpha         92.188(8)
_cell_oxdiff_angle_beta          99.326(13)
_cell_oxdiff_angle_gamma         104.527(9)
_cell_oxdiff_volume              889.8(2)
_cell_oxdiff_measurement_reflns_used 1693
#END Tags that were not found in dictionaries
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
Pd1 Pd 0.42193(7) 1.01649(4) 0.12133(3) 0.0586(2) Uani 1 1 d .
Cl1 Cl 0.6318(3) 1.15553(15) 0.01637(13) 0.0815(6) Uani 1 1 d .
Cl2 Cl 0.4883(3) 1.19535(18) 0.24941(13) 0.0800(5) Uani 1 1 d .
P1 P 0.2512(2) 0.87771(16) 0.22237(12) 0.0560(4) Uani 1 1 d .
F1 F -0.1599(8) 1.0442(6) 0.4093(4) 0.1235(18) Uani 1 1 d .
F2 F -0.0815(9) 1.3199(6) 0.4354(5) 0.156(3) Uani 1 1 d .
F3 F 0.0801(11) 1.3409(6) 0.3092(7) 0.174(3) Uani 1 1 d .
C1 C 0.1430(10) 0.9603(6) 0.3157(5) 0.0656(17) Uani 1 1 d .
H1A H 0.0739 0.8893 0.3552 0.079 Uiso 1 1 calc R
H1B H 0.2423 1.0232 0.3672 0.079 Uiso 1 1 calc R
C2 C 0.0076(11) 1.0418(8) 0.2628(6) 0.081(2) Uani 1 1 d .
H2A H 0.0710 1.1054 0.2162 0.098 Uiso 1 1 calc R
H2B H -0.1015 0.9776 0.2189 0.098 Uiso 1 1 calc R
C3 C -0.0570(11) 1.1220(8) 0.3448(6) 0.082(2) Uani 1 1 d .
C4 C -0.0248(15) 1.2519(10) 0.3605(9) 0.112(3) Uani 1 1 d .
C11 C 0.4028(9) 0.7882(6) 0.3013(5) 0.0599(16) Uani 1 1 d .
C12 C 0.4222(12) 0.7872(8) 0.4106(5) 0.082(2) Uani 1 1 d .
H12 H 0.3601 0.8378 0.4484 0.098 Uiso 1 1 calc R
C13 C 0.5346(14) 0.7106(9) 0.4652(6) 0.105(3) Uani 1 1 d .
H13 H 0.5473 0.7111 0.5396 0.127 Uiso 1 1 calc R
C14 C 0.6241(13) 0.6367(10) 0.4138(7) 0.103(3) Uani 1 1 d .
H14 H 0.6974 0.5846 0.4512 0.124 Uiso 1 1 calc R
C15 C 0.6068(13) 0.6386(10) 0.3064(7) 0.106(3) Uani 1 1 d .
H15 H 0.6694 0.5876 0.2693 0.127 Uiso 1 1 calc R
C16 C 0.4989(11) 0.7141(8) 0.2511(6) 0.083(2) Uani 1 1 d .
H16 H 0.4910 0.7146 0.1770 0.099 Uiso 1 1 calc R
C21 C 0.0584(8) 0.7441(6) 0.1444(5) 0.0571(15) Uani 1 1 d .
C22 C 0.0208(10) 0.6101(7) 0.1737(6) 0.0724(18) Uani 1 1 d .
H22 H 0.0957 0.5869 0.2328 0.087 Uiso 1 1 calc R
C23 C -0.1298(11) 0.5096(7) 0.1142(7) 0.087(2) Uani 1 1 d .
H23 H -0.1558 0.4184 0.1333 0.104 Uiso 1 1 calc R
C24 C -0.2379(11) 0.5438(8) 0.0294(7) 0.083(2) Uani 1 1 d .
H24 H -0.3380 0.4752 -0.0099 0.100 Uiso 1 1 calc R
C25 C -0.2052(11) 0.6770(9) -0.0011(6) 0.088(2) Uani 1 1 d .
H25 H -0.2813 0.6991 -0.0603 0.105 Uiso 1 1 calc R
C26 C -0.0567(10) 0.7772(8) 0.0580(6) 0.078(2) Uani 1 1 d .
H26 H -0.0336 0.8686 0.0393 0.094 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'
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'
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'
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
7 -9 10 0.1028 7.0000 -9.0000 10.0000 0.1842 0.5180 0.8912
2 13 -4 0.1082 2.0000 13.0000 -4.0000 -0.3441 -0.9602 0.1407
-8 6 -9 0.0983 -8.0000 6.0000 -9.0000 -0.0767 -0.2894 -0.9686
-4 -11 2 0.1011 -4.0000 -11.0000 2.0000 0.3335 0.8501 -0.3704
-2 3 17 0.0832 -2.0000 3.0000 17.0000 0.8466 -0.2692 0.4282
7 -5 -14 0.0500 7.0000 -5.0000 -14.0000 -0.9274 0.3339 0.1010
-7 5 14 0.1103 -7.0000 5.0000 14.0000 0.9274 -0.3339 -0.1010
2 12 -6 0.0669 2.0000 12.0000 -6.0000 -0.4294 -0.8780 0.0645
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
P1 Pd1 Cl2 90.61(6) . .
P1 Pd1 Cl1 93.53(6) . 2_675
Cl2 Pd1 Cl1 175.85(6) . 2_675
P1 Pd1 Cl1 174.30(7) . .
Cl2 Pd1 Cl1 90.82(6) . .
Cl1 Pd1 Cl1 85.03(5) 2_675 .
Pd1 Cl1 Pd1 94.97(5) 2_675 .
C11 P1 C21 106.3(3) . .
C11 P1 C1 106.8(3) . .
C21 P1 C1 105.0(3) . .
C11 P1 Pd1 108.3(2) . .
C21 P1 Pd1 113.16(19) . .
C1 P1 Pd1 116.6(2) . .
C2 C1 P1 114.4(4) . .
C3 C2 C1 111.5(6) . .
C4 C3 F1 117.2(8) . .
C4 C3 C2 127.8(9) . .
F1 C3 C2 115.0(7) . .
C3 C4 F3 124.6(10) . .
C3 C4 F2 126.3(11) . .
F3 C4 F2 109.0(8) . .
C16 C11 C12 117.2(7) . .
C16 C11 P1 119.4(5) . .
C12 C11 P1 123.4(5) . .
C11 C12 C13 120.0(7) . .
C14 C13 C12 121.6(8) . .
C13 C14 C15 118.5(8) . .
C14 C15 C16 121.0(8) . .
C11 C16 C15 121.7(7) . .
C22 C21 C26 119.4(6) . .
C22 C21 P1 120.2(5) . .
C26 C21 P1 120.3(5) . .
C21 C22 C23 119.5(7) . .
C24 C23 C22 120.0(7) . .
C23 C24 C25 121.9(7) . .
C24 C25 C26 118.3(7) . .
C25 C26 C21 120.9(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 P1 2.2202(15) .
Pd1 Cl2 2.2636(16) .
Pd1 Cl1 2.3098(15) 2_675
Pd1 Cl1 2.4149(15) .
Cl1 Pd1 2.3098(15) 2_675
P1 C11 1.807(6) .
P1 C21 1.810(6) .
P1 C1 1.811(6) .
F1 C3 1.343(9) .
F2 C4 1.325(10) .
F3 C4 1.294(11) .
C1 C2 1.532(9) .
C2 C3 1.495(9) .
C3 C4 1.257(11) .
C11 C16 1.353(8) .
C11 C12 1.367(8) .
C12 C13 1.388(10) .
C13 C14 1.325(10) .
C14 C15 1.345(10) .
C15 C16 1.362(10) .
C21 C22 1.372(8) .
C21 C26 1.378(9) .
C22 C23 1.388(10) .
C23 C24 1.341(10) .
C24 C25 1.370(10) .
C25 C26 1.376(10) .
