#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:07:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178550 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/57/4065786.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_4065786
loop_
_publ_author_name
'Debono, Nathalie'
'Labande, Agnès'
'Manoury, Eric'
'Daran, Jean-Claude'
'Poli, Rinaldo'
_publ_section_title
;
 Palladium Complexes of Planar Chiral Ferrocenyl Phosphine-NHC Ligands:
 New Catalysts for the Asymmetric Suzuki−Miyaura Reaction
;
_journal_issue                   8
_journal_name_full               Organometallics
_journal_page_first              1879
_journal_paper_doi               10.1021/om100125k
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C27 H25 Cl2 Fe N2 P Pd, C H2 Cl2'
_chemical_formula_sum            'C28 H27 Cl4 Fe N2 P Pd'
_chemical_formula_weight         726.54
_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                81.134(3)
_cell_angle_beta                 71.512(3)
_cell_angle_gamma                73.000(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8781(4)
_cell_length_b                   10.7098(5)
_cell_length_c                   14.9399(7)
_cell_measurement_reflns_used    9596
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      29.92
_cell_measurement_theta_min      1.44
_cell_volume                     1430.17(12)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector, APEXII'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            50442
_diffrn_reflns_theta_full        29.92
_diffrn_reflns_theta_max         29.92
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    1.587
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.344
_exptl_crystal_size_min          0.015
_refine_diff_density_max         1.113
_refine_diff_density_min         -0.824
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         8151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0525P)²+2.5333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                6404
_reflns_number_total             8151
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om100125k_si_002.cif
_cod_data_source_block           2a(rac)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1430.17(11)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4065786
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 1.07290(3) 0.38250(2) 0.228555(17) 0.01837(7) Uani 1 1 d .
Cl1 Cl 1.29243(9) 0.36503(9) 0.10222(6) 0.02809(18) Uani 1 1 d .
Cl2 Cl 1.18004(9) 0.19333(8) 0.30908(6) 0.02868(18) Uani 1 1 d .
P1 P 0.84857(9) 0.41483(8) 0.33472(6) 0.01710(16) Uani 1 1 d .
Fe1 Fe 0.66526(5) 0.26505(5) 0.23311(4) 0.02338(11) Uani 1 1 d .
N1 N 0.8877(3) 0.5689(3) 0.1171(2) 0.0229(6) Uani 1 1 d .
N2 N 1.0109(4) 0.6671(3) 0.1633(2) 0.0269(6) Uani 1 1 d .
C1 C 0.7069(4) 0.4107(3) 0.2852(2) 0.0203(6) Uani 1 1 d .
C2 C 0.7031(4) 0.4426(3) 0.1884(2) 0.0214(6) Uani 1 1 d .
C3 C 0.5598(4) 0.4443(3) 0.1854(3) 0.0270(7) Uani 1 1 d .
H3 H 0.5256 0.4652 0.1308 0.032 Uiso 1 1 calc R
C4 C 0.4767(4) 0.4095(4) 0.2776(3) 0.0291(7) Uani 1 1 d .
H4 H 0.3783 0.4011 0.2951 0.035 Uiso 1 1 calc R
C5 C 0.5658(4) 0.3894(3) 0.3390(3) 0.0252(7) Uani 1 1 d .
H5 H 0.5369 0.3658 0.4049 0.030 Uiso 1 1 calc R
C6 C 0.7999(5) 0.1385(4) 0.1323(3) 0.0381(9) Uani 1 1 d .
H6 H 0.8655 0.1598 0.0737 0.046 Uiso 1 1 calc R
C7 C 0.8348(4) 0.0993(3) 0.2178(3) 0.0325(8) Uani 1 1 d .
H7 H 0.9277 0.0905 0.2275 0.039 Uiso 1 1 calc R
C8 C 0.7080(5) 0.0749(4) 0.2874(3) 0.0428(10) Uani 1 1 d .
H8 H 0.7009 0.0463 0.3518 0.051 Uiso 1 1 calc R
C9 C 0.5938(5) 0.1007(4) 0.2439(4) 0.0471(11) Uani 1 1 d .
H9 H 0.4962 0.0924 0.2740 0.056 Uiso 1 1 calc R
C10 C 0.6500(5) 0.1411(4) 0.1482(4) 0.0432(10) Uani 1 1 d .
H10 H 0.5968 0.1655 0.1025 0.052 Uiso 1 1 calc R
C21 C 0.8286(4) 0.4644(3) 0.1047(2) 0.0247(7) Uani 1 1 d .
H21A H 0.9085 0.3823 0.0946 0.030 Uiso 1 1 calc R
H21B H 0.7938 0.4872 0.0475 0.030 Uiso 1 1 calc R
C22 C 0.9858(4) 0.5504(3) 0.1649(2) 0.0216(6) Uani 1 1 d .
C23 C 0.8481(4) 0.6989(3) 0.0847(3) 0.0304(8) Uani 1 1 d .
H23 H 0.7805 0.7369 0.0487 0.036 Uiso 1 1 calc R
C24 C 0.9253(4) 0.7603(4) 0.1150(3) 0.0327(8) Uani 1 1 d .
H24 H 0.9215 0.8508 0.1049 0.039 Uiso 1 1 calc R
C25 C 1.1147(5) 0.6921(4) 0.2039(3) 0.0411(10) Uani 1 1 d .
H25A H 1.1685 0.6094 0.2294 0.062 Uiso 1 1 calc R
H25B H 1.0610 0.7513 0.2550 0.062 Uiso 1 1 calc R
H25C H 1.1849 0.7325 0.1549 0.062 Uiso 1 1 calc R
C111 C 0.7925(4) 0.5770(3) 0.3786(2) 0.0202(6) Uani 1 1 d .
C112 C 0.6561(4) 0.6636(3) 0.3811(3) 0.0269(7) Uani 1 1 d .
H112 H 0.5927 0.6440 0.3520 0.032 Uiso 1 1 calc R
C113 C 0.6123(5) 0.7796(4) 0.4264(3) 0.0369(9) Uani 1 1 d .
H113 H 0.5193 0.8393 0.4278 0.044 Uiso 1 1 calc R
C114 C 0.7038(5) 0.8074(4) 0.4692(3) 0.0366(9) Uani 1 1 d .
H114 H 0.6717 0.8847 0.5022 0.044 Uiso 1 1 calc R
C115 C 0.8417(5) 0.7240(4) 0.4644(3) 0.0354(9) Uani 1 1 d .
H115 H 0.9056 0.7450 0.4923 0.042 Uiso 1 1 calc R
C116 C 0.8862(4) 0.6093(3) 0.4185(3) 0.0280(7) Uani 1 1 d .
H116 H 0.9817 0.5523 0.4142 0.034 Uiso 1 1 calc R
C121 C 0.8165(3) 0.3106(3) 0.4439(2) 0.0196(6) Uani 1 1 d .
C122 C 0.8549(4) 0.1754(3) 0.4402(3) 0.0243(7) Uani 1 1 d .
H122 H 0.9007 0.1377 0.3809 0.029 Uiso 1 1 calc R
C123 C 0.8271(4) 0.0954(4) 0.5223(3) 0.0295(8) Uani 1 1 d .
H123 H 0.8526 0.0032 0.5188 0.035 Uiso 1 1 calc R
C124 C 0.7623(4) 0.1489(4) 0.6096(3) 0.0317(8) Uani 1 1 d .
H124 H 0.7451 0.0936 0.6659 0.038 Uiso 1 1 calc R
C125 C 0.7228(4) 0.2834(4) 0.6141(3) 0.0294(7) Uani 1 1 d .
H125 H 0.6769 0.3206 0.6736 0.035 Uiso 1 1 calc R
C126 C 0.7501(4) 0.3640(3) 0.5318(2) 0.0251(7) Uani 1 1 d .
H126 H 0.7234 0.4562 0.5353 0.030 Uiso 1 1 calc R
C11 C 0.3544(6) 1.0128(5) 0.1136(4) 0.0489(11) Uani 1 1 d .
H11A H 0.3131 1.0566 0.1738 0.059 Uiso 1 1 calc R
H11B H 0.4204 1.0625 0.0682 0.059 Uiso 1 1 calc R
Cl11 Cl 0.21147(18) 1.01410(14) 0.06943(11) 0.0652(4) Uani 1 1 d .
Cl12 Cl 0.45706(15) 0.85307(16) 0.13337(11) 0.0705(4) 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'
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'
Fe Fe 0.3463 0.8444 '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
C22 Pd1 P1 84.95(9)
C22 Pd1 Cl2 176.17(10)
P1 Pd1 Cl2 95.06(3)
C22 Pd1 Cl1 88.24(9)
P1 Pd1 Cl1 172.34(3)
Cl2 Pd1 Cl1 91.97(3)
C1 P1 C111 105.19(15)
C1 P1 C121 103.91(15)
C111 P1 C121 102.23(15)
C1 P1 Pd1 112.90(11)
C111 P1 Pd1 110.17(11)
C121 P1 Pd1 120.90(10)
C2 Fe1 C5 69.60(14)
C2 Fe1 C4 69.44(14)
C5 Fe1 C4 40.66(14)
C2 Fe1 C7 121.17(15)
C5 Fe1 C7 132.08(15)
C4 Fe1 C7 166.76(16)
C2 Fe1 C10 124.30(18)
C5 Fe1 C10 149.38(17)
C4 Fe1 C10 113.89(17)
C7 Fe1 C10 68.03(17)
C2 Fe1 C3 41.15(13)
C5 Fe1 C3 68.56(15)
C4 Fe1 C3 40.75(15)
C7 Fe1 C3 152.47(16)
C10 Fe1 C3 103.11(17)
C2 Fe1 C1 41.71(13)
C5 Fe1 C1 41.26(13)
C4 Fe1 C1 69.26(14)
C7 Fe1 C1 112.52(14)
C10 Fe1 C1 165.06(18)
C3 Fe1 C1 69.26(13)
C2 Fe1 C6 107.56(16)
C5 Fe1 C6 169.54(16)
C4 Fe1 C6 148.82(17)
C7 Fe1 C6 40.08(17)
C10 Fe1 C6 40.62(18)
C3 Fe1 C6 116.39(17)
C1 Fe1 C6 130.12(16)
C2 Fe1 C9 161.15(18)
C5 Fe1 C9 118.14(18)
C4 Fe1 C9 104.54(17)
C7 Fe1 C9 67.95(18)
C10 Fe1 C9 40.4(2)
C3 Fe1 C9 122.96(18)
C1 Fe1 C9 154.52(18)
C6 Fe1 C9 67.86(19)
C2 Fe1 C8 156.65(17)
C5 Fe1 C8 110.60(17)
C4 Fe1 C8 126.89(18)
C7 Fe1 C8 40.49(18)
C10 Fe1 C8 68.0(2)
C3 Fe1 C8 162.03(17)
C1 Fe1 C8 122.79(17)
C6 Fe1 C8 67.76(19)
C9 Fe1 C8 40.4(2)
C22 N1 C23 110.7(3)
C22 N1 C21 123.2(3)
C23 N1 C21 126.0(3)
C22 N2 C24 109.8(3)
C22 N2 C25 125.4(3)
C24 N2 C25 124.8(3)
C5 C1 C2 106.8(3)
C5 C1 P1 124.9(3)
C2 C1 P1 127.9(2)
C5 C1 Fe1 69.17(19)
C2 C1 Fe1 68.29(18)
P1 C1 Fe1 132.95(17)
C3 C2 C1 107.7(3)
C3 C2 C21 125.6(3)
C1 C2 C21 126.6(3)
C3 C2 Fe1 70.3(2)
C1 C2 Fe1 70.00(18)
C21 C2 Fe1 123.2(2)
C4 C3 C2 108.5(3)
C4 C3 Fe1 69.6(2)
C2 C3 Fe1 68.57(19)
C5 C4 C3 108.1(3)
C5 C4 Fe1 69.6(2)
C3 C4 Fe1 69.7(2)
C4 C5 C1 108.8(3)
C4 C5 Fe1 69.8(2)
C1 C5 Fe1 69.57(19)
C7 C6 C10 108.1(4)
C7 C6 Fe1 69.7(2)
C10 C6 Fe1 69.5(2)
C6 C7 C8 108.4(4)
C6 C7 Fe1 70.2(2)
C8 C7 Fe1 70.1(2)
C7 C8 C9 107.6(4)
C7 C8 Fe1 69.4(2)
C9 C8 Fe1 69.8(3)
C10 C9 C8 108.1(4)
C10 C9 Fe1 69.5(2)
C8 C9 Fe1 69.8(2)
C9 C10 C6 107.8(4)
C9 C10 Fe1 70.1(2)
C6 C10 Fe1 69.9(2)
N1 C21 C2 112.2(3)
N1 C22 N2 106.4(3)
N1 C22 Pd1 126.3(2)
N2 C22 Pd1 127.3(3)
C24 C23 N1 105.8(3)
C23 C24 N2 107.3(3)
C112 C111 C116 119.4(3)
C112 C111 P1 122.7(3)
C116 C111 P1 117.6(3)
C111 C112 C113 119.8(3)
C114 C113 C112 120.0(4)
C113 C114 C115 120.6(4)
C114 C115 C116 119.5(4)
C115 C116 C111 120.5(3)
C122 C121 C126 118.8(3)
C122 C121 P1 119.9(3)
C126 C121 P1 121.2(2)
C123 C122 C121 120.5(3)
C122 C123 C124 120.4(3)
C125 C124 C123 119.6(3)
C124 C125 C126 120.1(3)
C125 C126 C121 120.5(3)
Cl11 C11 Cl12 111.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C22 1.991(3)
Pd1 P1 2.2444(8)
Pd1 Cl2 2.3397(8)
Pd1 Cl1 2.3614(9)
P1 C1 1.791(3)
P1 C111 1.820(3)
P1 C121 1.823(3)
Fe1 C2 2.017(3)
Fe1 C5 2.034(3)
Fe1 C4 2.038(4)
Fe1 C7 2.038(4)
Fe1 C10 2.038(4)
Fe1 C3 2.039(4)
Fe1 C1 2.040(3)
Fe1 C6 2.044(4)
Fe1 C9 2.046(4)
Fe1 C8 2.047(4)
N1 C22 1.331(4)
N1 C23 1.385(4)
N1 C21 1.464(4)
N2 C22 1.339(4)
N2 C24 1.379(5)
N2 C25 1.448(5)
C1 C5 1.435(5)
C1 C2 1.444(5)
C2 C3 1.426(5)
C2 C21 1.501(5)
C3 C4 1.420(5)
C4 C5 1.415(5)
C6 C7 1.399(6)
C6 C10 1.417(6)
C7 C8 1.413(6)
C8 C9 1.414(7)
C9 C10 1.409(7)
C23 C24 1.350(6)
C111 C112 1.387(5)
C111 C116 1.390(5)
C112 C113 1.396(5)
C113 C114 1.377(6)
C114 C115 1.380(6)
C115 C116 1.388(5)
C121 C122 1.390(4)
C121 C126 1.396(5)
C122 C123 1.383(5)
C123 C124 1.389(6)
C124 C125 1.384(5)
C125 C126 1.389(5)
C11 Cl11 1.734(5)
C11 Cl12 1.749(5)
