#------------------------------------------------------------------------------
#$Date: 2018-08-17 00:36:15 +0300 (Fri, 17 Aug 2018) $
#$Revision: 209826 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/46/4074685.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_4074685
loop_
_publ_author_name
'Teo, Shihui'
'Weng, Zhiqiang'
'Hor, T. S. Andy'
_publ_section_title
;
 1,1'-P/O-Ferrocenyl Ligands in Palladium-Catalyzed Suzuki Coupling
 of Aryl Chlorides
;
_journal_coden_ASTM              ORGND7
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1199
_journal_page_last               1205
_journal_paper_doi               10.1021/om050791j
_journal_volume                  25
_journal_year                    2006
_chemical_formula_sum            'C56 H70 F5 Fe2 I O4 P2 Pd'
_chemical_formula_weight         1309.06
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 114.753(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.9960(15)
_cell_length_b                   19.5414(15)
_cell_length_c                   17.0394(15)
_cell_measurement_reflns_used    602
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      17.94
_cell_measurement_theta_min      2.40
_cell_volume                     5441.6(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      243(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1337
_diffrn_reflns_av_sigmaI/netI    0.1413
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15772
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_T_max  0.9552
_exptl_absorpt_correction_T_min  0.8866
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Thin Plate'
_exptl_crystal_F_000             2656
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.974
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0771
_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)+(0.0539P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                2692
_reflns_number_total             4788
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om050791jsi20050913_114729.cif
_cod_data_source_block           5342
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      C2/c
_cod_database_code               4074685
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.0000 0.29692(5) 0.7500 0.0253(3) Uani 1 2 d S
I1 I 0.0000 0.43228(5) 0.7500 0.0487(3) Uani 1 2 d S
Fe1 Fe 0.06531(10) 0.16023(8) 0.49996(11) 0.0538(5) Uani 1 1 d .
P1 P 0.03554(14) 0.29363(13) 0.63190(16) 0.0307(6) Uani 1 1 d .
O1 O 0.2416(5) 0.0766(5) 0.6200(7) 0.101(4) Uani 1 1 d .
O2 O 0.3162(5) 0.1192(4) 0.5531(6) 0.070(2) Uani 1 1 d .
C1 C 0.0000 0.1948(5) 0.7500 0.032(3) Uani 1 2 d S
C2 C 0.0653(6) 0.1565(4) 0.8057(6) 0.034(2) Uani 1 1 d .
F2 F 0.1331(3) 0.1888(2) 0.8634(4) 0.0474(15) Uani 1 1 d .
C3 C 0.0653(6) 0.0856(5) 0.8048(8) 0.048(3) Uani 1 1 d .
F3 F 0.1312(4) 0.0517(3) 0.8627(5) 0.075(2) Uani 1 1 d .
C4 C 0.0000 0.0525(7) 0.7500 0.057(5) Uani 1 2 d S
F4 F 0.0000 -0.0167(4) 0.7500 0.107(4) Uani 1 2 d S
C5 C 0.2514(7) 0.1349(7) 0.5772(8) 0.068(3) Uani 1 1 d .
H5 H 0.2669 0.1745 0.6171 0.082 Uiso 1 1 calc R
C6 C 0.3118(8) 0.0356(7) 0.6444(9) 0.084(4) Uani 1 1 d .
H6A H 0.2986 -0.0087 0.6148 0.101 Uiso 1 1 calc R
H6B H 0.3369 0.0278 0.7069 0.101 Uiso 1 1 calc R
C7 C 0.3685(8) 0.0770(6) 0.6164(9) 0.081(4) Uani 1 1 d .
H7A H 0.4077 0.1036 0.6648 0.098 Uiso 1 1 calc R
H7B H 0.3985 0.0471 0.5937 0.098 Uiso 1 1 calc R
C8 C 0.0287(6) 0.2085(5) 0.5853(7) 0.040(2) Uani 1 1 d .
C9 C -0.0402(7) 0.1786(5) 0.5153(7) 0.053(3) Uani 1 1 d .
H9 H -0.0888 0.2037 0.4743 0.063 Uiso 1 1 calc R
C10 C -0.0267(8) 0.1084(6) 0.5146(9) 0.067(4) Uani 1 1 d .
H10 H -0.0642 0.0748 0.4735 0.081 Uiso 1 1 calc R
C11 C 0.0486(9) 0.0942(6) 0.5806(9) 0.063(4) Uani 1 1 d .
H11 H 0.0736 0.0482 0.5949 0.076 Uiso 1 1 calc R
C12 C 0.0840(7) 0.1541(5) 0.6247(7) 0.048(3) Uani 1 1 d .
H12 H 0.1374 0.1579 0.6755 0.058 Uiso 1 1 calc R
C13 C 0.1449(8) 0.2162(6) 0.4704(9) 0.063(4) Uani 1 1 d .
H13 H 0.1703 0.2603 0.4963 0.076 Uiso 1 1 calc R
C14 C 0.0717(9) 0.2064(9) 0.3949(8) 0.086(5) Uani 1 1 d .
H14 H 0.0352 0.2433 0.3599 0.104 Uiso 1 1 calc R
C15 C 0.0586(10) 0.1374(9) 0.3793(10) 0.103(6) Uani 1 1 d .
H15 H 0.0118 0.1159 0.3311 0.124 Uiso 1 1 calc R
C16 C 0.1230(8) 0.1040(6) 0.4427(9) 0.068(4) Uani 1 1 d .
H16 H 0.1303 0.0537 0.4476 0.082 Uiso 1 1 calc R
C17 C 0.1754(6) 0.1510(6) 0.4989(7) 0.051(3) Uani 1 1 d .
C18 C -0.0324(5) 0.3498(4) 0.5434(6) 0.037(2) Uani 1 1 d .
H18 H -0.0172 0.3970 0.5650 0.045 Uiso 1 1 calc R
C19 C -0.1215(5) 0.3419(5) 0.5281(7) 0.046(3) Uani 1 1 d .
H19A H -0.1268 0.3482 0.5826 0.056 Uiso 1 1 calc R
H19B H -0.1408 0.2958 0.5064 0.056 Uiso 1 1 calc R
C20 C -0.1730(6) 0.3950(6) 0.4626(7) 0.057(3) Uani 1 1 d .
H20A H -0.2307 0.3884 0.4509 0.068 Uiso 1 1 calc R
H20B H -0.1568 0.4408 0.4872 0.068 Uiso 1 1 calc R
C21 C -0.1640(7) 0.3907(6) 0.3794(8) 0.072(4) Uani 1 1 d .
H21A H -0.1973 0.4264 0.3400 0.086 Uiso 1 1 calc R
H21B H -0.1840 0.3462 0.3523 0.086 Uiso 1 1 calc R
C22 C -0.0743(7) 0.3995(6) 0.3945(8) 0.068(4) Uani 1 1 d .
H22A H -0.0694 0.3940 0.3397 0.082 Uiso 1 1 calc R
H22B H -0.0556 0.4457 0.4164 0.082 Uiso 1 1 calc R
C23 C -0.0211(6) 0.3464(5) 0.4595(6) 0.051(3) Uani 1 1 d .
H23A H -0.0357 0.3006 0.4344 0.061 Uiso 1 1 calc R
H23B H 0.0365 0.3546 0.4720 0.061 Uiso 1 1 calc R
C24 C 0.1430(5) 0.3203(5) 0.6605(6) 0.036(2) Uani 1 1 d .
H24 H 0.1603 0.2960 0.6199 0.043 Uiso 1 1 calc R
C25 C 0.1570(6) 0.3965(5) 0.6512(8) 0.053(3) Uani 1 1 d .
H25A H 0.1234 0.4111 0.5917 0.064 Uiso 1 1 calc R
H25B H 0.1400 0.4230 0.6897 0.064 Uiso 1 1 calc R
C26 C 0.2448(7) 0.4110(6) 0.6727(9) 0.068(4) Uani 1 1 d .
H26A H 0.2596 0.3887 0.6297 0.082 Uiso 1 1 calc R
H26B H 0.2517 0.4605 0.6687 0.082 Uiso 1 1 calc R
C27 C 0.3007(7) 0.3877(6) 0.7589(8) 0.068(4) Uani 1 1 d .
H27A H 0.2909 0.4140 0.8026 0.081 Uiso 1 1 calc R
H27B H 0.3573 0.3958 0.7674 0.081 Uiso 1 1 calc R
C28 C 0.2887(6) 0.3131(7) 0.7698(9) 0.083(4) Uani 1 1 d .
H28A H 0.3242 0.2995 0.8292 0.099 Uiso 1 1 calc R
H28B H 0.3052 0.2868 0.7308 0.099 Uiso 1 1 calc R
C29 C 0.2001(6) 0.2957(6) 0.7512(8) 0.066(3) Uani 1 1 d .
H29A H 0.1850 0.3178 0.7941 0.080 Uiso 1 1 calc R
H29B H 0.1944 0.2461 0.7553 0.080 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'
P P 0.1023 0.0942 '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'
I I -0.4742 1.8119 '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
C1 Pd1 P1 88.44(7) . 2_556
C1 Pd1 P1 88.44(6) . .
P1 Pd1 P1 176.87(13) 2_556 .
C1 Pd1 I1 180.000(1) . .
P1 Pd1 I1 91.56(7) 2_556 .
P1 Pd1 I1 91.56(7) . .
C17 Fe1 C11 112.6(5) . .
C17 Fe1 C12 106.1(4) . .
C11 Fe1 C12 40.7(4) . .
C17 Fe1 C16 40.0(4) . .
C11 Fe1 C16 103.7(5) . .
C12 Fe1 C16 125.8(5) . .
C17 Fe1 C13 40.5(4) . .
C11 Fe1 C13 147.7(6) . .
C12 Fe1 C13 118.1(5) . .
C16 Fe1 C13 67.3(5) . .
C17 Fe1 C10 144.5(5) . .
C11 Fe1 C10 39.9(5) . .
C12 Fe1 C10 68.1(5) . .
C16 Fe1 C10 113.3(5) . .
C13 Fe1 C10 172.4(6) . .
C17 Fe1 C14 67.2(5) . .
C11 Fe1 C14 164.7(6) . .
C12 Fe1 C14 154.5(6) . .
C16 Fe1 C14 65.8(6) . .
C13 Fe1 C14 40.7(5) . .
C10 Fe1 C14 132.0(6) . .
C17 Fe1 C9 172.1(4) . .
C11 Fe1 C9 67.1(5) . .
C12 Fe1 C9 68.3(4) . .
C16 Fe1 C9 147.7(5) . .
C13 Fe1 C9 136.5(5) . .
C10 Fe1 C9 39.8(4) . .
C14 Fe1 C9 115.3(5) . .
C17 Fe1 C15 67.3(5) . .
C11 Fe1 C15 125.8(6) . .
C12 Fe1 C15 163.1(6) . .
C16 Fe1 C15 39.4(5) . .
C13 Fe1 C15 67.7(5) . .
C10 Fe1 C15 107.6(5) . .
C14 Fe1 C15 39.1(5) . .
C9 Fe1 C15 119.6(5) . .
C17 Fe1 C8 131.3(4) . .
C11 Fe1 C8 68.0(4) . .
C12 Fe1 C8 40.7(4) . .
C16 Fe1 C8 166.1(5) . .
C13 Fe1 C8 113.4(4) . .
C10 Fe1 C8 68.0(4) . .
C14 Fe1 C8 124.5(5) . .
C9 Fe1 C8 40.9(4) . .
C15 Fe1 C8 154.5(6) . .
C8 P1 C18 106.5(5) . .
C8 P1 C24 104.0(4) . .
C18 P1 C24 107.9(4) . .
C8 P1 Pd1 113.8(3) . .
C18 P1 Pd1 110.9(3) . .
C24 P1 Pd1 113.2(3) . .
C5 O1 C6 108.9(9) . .
C7 O2 C5 106.2(9) . .
C2 C1 C2 114.3(11) . 2_556
C2 C1 Pd1 122.8(5) . .
C2 C1 Pd1 122.8(5) 2_556 .
F2 C2 C1 119.5(7) . .
F2 C2 C3 118.0(8) . .
C1 C2 C3 122.5(9) . .
C4 C3 F3 121.5(9) . .
C4 C3 C2 119.6(10) . .
F3 C3 C2 118.9(9) . .
C3 C4 C3 121.5(13) . 2_556
C3 C4 F4 119.3(7) . .
C3 C4 F4 119.3(7) 2_556 .
O1 C5 O2 105.8(9) . .
O1 C5 C17 111.6(10) . .
O2 C5 C17 110.1(10) . .
O1 C6 C7 104.0(10) . .
O2 C7 C6 103.7(10) . .
C12 C8 C9 106.3(9) . .
C12 C8 P1 124.8(8) . .
C9 C8 P1 127.5(8) . .
C12 C8 Fe1 67.8(6) . .
C9 C8 Fe1 69.4(6) . .
P1 C8 Fe1 137.8(5) . .
C10 C9 C8 108.3(10) . .
C10 C9 Fe1 69.7(6) . .
C8 C9 Fe1 69.7(6) . .
C11 C10 C9 107.8(10) . .
C11 C10 Fe1 68.2(7) . .
C9 C10 Fe1 70.5(6) . .
C10 C11 C12 110.0(10) . .
C10 C11 Fe1 71.9(8) . .
C12 C11 Fe1 70.2(7) . .
C11 C12 C8 107.6(10) . .
C11 C12 Fe1 69.1(7) . .
C8 C12 Fe1 71.4(6) . .
C17 C13 C14 105.9(11) . .
C17 C13 Fe1 68.6(6) . .
C14 C13 Fe1 70.6(8) . .
C15 C14 C13 109.1(13) . .
C15 C14 Fe1 70.7(9) . .
C13 C14 Fe1 68.7(7) . .
C16 C15 C14 107.1(13) . .
C16 C15 Fe1 68.9(8) . .
C14 C15 Fe1 70.2(8) . .
C15 C16 C17 109.6(12) . .
C15 C16 Fe1 71.7(8) . .
C17 C16 Fe1 69.0(6) . .
C16 C17 C13 108.3(11) . .
C16 C17 C5 125.9(11) . .
C13 C17 C5 125.8(11) . .
C16 C17 Fe1 71.0(6) . .
C13 C17 Fe1 70.9(6) . .
C5 C17 Fe1 123.6(8) . .
C19 C18 C23 112.3(8) . .
C19 C18 P1 111.6(6) . .
C23 C18 P1 115.9(6) . .
C18 C19 C20 109.3(8) . .
C21 C20 C19 112.5(9) . .
C20 C21 C22 111.1(9) . .
C23 C22 C21 109.9(9) . .
C18 C23 C22 111.2(9) . .
C29 C24 C25 109.8(9) . .
C29 C24 P1 111.2(7) . .
C25 C24 P1 116.4(6) . .
C26 C25 C24 111.3(8) . .
C27 C26 C25 113.6(10) . .
C26 C27 C28 110.8(10) . .
C27 C28 C29 112.5(10) . .
C28 C29 C24 109.9(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 1.995(11) .
Pd1 P1 2.354(2) 2_556
Pd1 P1 2.354(2) .
Pd1 I1 2.6452(13) .
Fe1 C17 1.997(10) .
Fe1 C11 1.997(12) .
Fe1 C12 2.012(11) .
Fe1 C16 2.022(11) .
Fe1 C13 2.026(12) .
Fe1 C10 2.044(12) .
Fe1 C14 2.050(13) .
Fe1 C9 2.055(11) .
Fe1 C15 2.057(15) .
Fe1 C8 2.059(9) .
P1 C8 1.826(9) .
P1 C18 1.852(9) .
P1 C24 1.859(9) .
O1 C5 1.403(13) .
O1 C6 1.404(13) .
O2 C7 1.371(13) .
O2 C5 1.421(12) .
C1 C2 1.382(10) .
C1 C2 1.382(10) 2_556
C2 F2 1.359(10) .
C2 C3 1.385(12) .
C3 C4 1.323(11) .
C3 F3 1.357(10) .
C4 C3 1.323(11) 2_556
C4 F4 1.352(14) .
C5 C17 1.491(15) .
C6 C7 1.525(16) .
C8 C12 1.417(13) .
C8 C9 1.437(13) .
C9 C10 1.394(14) .
C10 C11 1.379(16) .
C11 C12 1.393(14) .
C13 C17 1.391(14) .
C13 C14 1.417(16) .
C14 C15 1.375(18) .
C15 C16 1.375(18) .
C16 C17 1.376(14) .
C18 C19 1.521(12) .
C18 C23 1.527(13) .
C19 C20 1.522(13) .
C20 C21 1.494(15) .
C21 C22 1.534(15) .
C22 C23 1.528(13) .
C24 C29 1.531(13) .
C24 C25 1.531(12) .
C25 C26 1.491(14) .
C26 C27 1.462(15) .
C27 C28 1.496(15) .
C28 C29 1.529(14) .
