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#$Date: 2021-06-05 21:56:40 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266093 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/69/7706931.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_7706931
loop_
_publ_author_name
'Vosáhlo, Petr'
'Schulz, Jiří'
'Císařová, Ivana'
'Štěpnička, Petr'
_publ_section_title
;
 Cyclopalladation of a ferrocene acylphosphine and the reactivity of the
 C-H activated products.
;
_journal_issue                   18
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6232
_journal_page_last               6244
_journal_paper_doi               10.1039/d1dt00668a
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C46 H36 Cl2 Fe2 O2 P2 Pd2, C4 H8 O2'
_chemical_formula_sum            'C50 H44 Cl2 Fe2 O4 P2 Pd2'
_chemical_formula_weight         1166.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-03-19 deposited with the CCDC.	2021-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                108.712(3)
_cell_angle_beta                 92.984(3)
_cell_angle_gamma                98.230(3)
_cell_formula_units_Z            1
_cell_length_a                   8.5435(7)
_cell_length_b                   9.9630(9)
_cell_length_c                   14.3031(12)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.98
_cell_volume                     1134.99(17)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2017)'
_computing_publication_material  'PLATON (Spek, 2017)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_source         'I\mS micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22234
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.190
_exptl_absorpt_coefficient_mu    1.640
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.822
_refine_diff_density_min         -1.192
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0351P)²+2.3880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4575
_reflns_number_total             5205
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt00668a3.cif
_cod_data_source_block           pv296_sq
_cod_depositor_comments
'Adding full bibliography for 7706929--7706948.cif.'
_cod_database_code               7706931
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.685
_shelx_estimated_absorpt_t_max   0.923
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.46772(3) 0.13258(2) 0.60935(2) 0.01716(7) Uani 1 1 d . . . . .
Fe1 Fe 0.54214(6) 0.52698(5) 0.71871(3) 0.02591(11) Uani 1 1 d . . . . .
Cl1 Cl 0.47570(11) 0.11041(8) 0.43765(5) 0.02928(17) Uani 1 1 d . . . . .
P1 P 0.46332(8) 0.17332(7) 0.77016(5) 0.01624(14) Uani 1 1 d . . . . .
O1 O 0.3340(3) 0.3827(2) 0.90446(15) 0.0253(4) Uani 1 1 d . . . . .
C1 C 0.3518(4) 0.3988(3) 0.7413(2) 0.0233(6) Uani 1 1 d . . . . .
C2 C 0.4048(3) 0.3269(3) 0.6487(2) 0.0214(6) Uani 1 1 d . . . . .
C3 C 0.3950(4) 0.4177(3) 0.5886(2) 0.0268(6) Uani 1 1 d . . . . .
H3 H 0.422976 0.397772 0.522704 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3360(4) 0.5426(3) 0.6454(2) 0.0325(7) Uani 1 1 d . . . . .
H4 H 0.317329 0.619745 0.623232 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3098(4) 0.5329(3) 0.7403(3) 0.0303(7) Uani 1 1 d . . . . .
H5 H 0.271909 0.601857 0.793049 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7052(5) 0.6085(4) 0.8415(3) 0.0422(9) Uani 1 1 d . . . . .
H6 H 0.690885 0.598229 0.904400 0.051 Uiso 1 1 calc R U . . .
C7 C 0.7706(4) 0.5136(4) 0.7627(3) 0.0430(9) Uani 1 1 d . . . . .
H7 H 0.809326 0.429353 0.763885 0.052 Uiso 1 1 calc R U . . .
C8 C 0.7679(5) 0.5668(4) 0.6815(3) 0.0443(9) Uani 1 1 d . . . . .
H8 H 0.802965 0.523428 0.618527 0.053 Uiso 1 1 calc R U . . .
C9 C 0.7041(5) 0.6952(4) 0.7109(3) 0.0420(9) Uani 1 1 d . . . . .
H9 H 0.689704 0.754037 0.671498 0.050 Uiso 1 1 calc R U . . .
C10 C 0.6650(5) 0.7212(4) 0.8099(3) 0.0451(9) Uani 1 1 d . . . . .
H10 H 0.619826 0.800345 0.848076 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3707(3) 0.3404(3) 0.8203(2) 0.0182(5) Uani 1 1 d . . . . .
C12 C 0.3375(3) 0.0416(3) 0.8075(2) 0.0201(6) Uani 1 1 d . . . . .
C13 C 0.3384(4) 0.0507(4) 0.9065(2) 0.0316(7) Uani 1 1 d . . . . .
H13 H 0.414125 0.120626 0.955213 0.038 Uiso 1 1 calc R U . . .
C14 C 0.2286(4) -0.0427(4) 0.9339(3) 0.0385(8) Uani 1 1 d . . . . .
H14 H 0.228337 -0.036271 1.001614 0.046 Uiso 1 1 calc R U . . .
C15 C 0.1193(4) -0.1452(4) 0.8625(3) 0.0334(7) Uani 1 1 d . . . . .
H15 H 0.042715 -0.207778 0.881660 0.040 Uiso 1 1 calc R U . . .
C16 C 0.1207(4) -0.1571(3) 0.7642(3) 0.0315(7) Uani 1 1 d . . . . .
H16 H 0.047249 -0.229410 0.715344 0.038 Uiso 1 1 calc R U . . .
C17 C 0.2299(4) -0.0633(3) 0.7361(2) 0.0261(6) Uani 1 1 d . . . . .
H17 H 0.230713 -0.071109 0.668224 0.031 Uiso 1 1 calc R U . . .
C18 C 0.6564(3) 0.2118(3) 0.84267(18) 0.0113(5) Uani 1 1 d . . . . .
C19 C 0.6928(3) 0.3174(3) 0.9333(2) 0.0209(6) Uani 1 1 d . . . . .
H19 H 0.613133 0.368719 0.963810 0.025 Uiso 1 1 calc R U . . .
C20 C 0.8460(4) 0.3493(3) 0.9805(2) 0.0255(6) Uani 1 1 d . . . . .
H20 H 0.871558 0.423050 1.043143 0.031 Uiso 1 1 calc R U . . .
C21 C 0.9619(4) 0.2739(4) 0.9364(2) 0.0295(7) Uani 1 1 d . . . . .
H21 H 1.066944 0.296607 0.968875 0.035 Uiso 1 1 calc R U . . .
C22 C 0.9259(4) 0.1659(4) 0.8457(3) 0.0321(7) Uani 1 1 d . . . . .
H22 H 1.005600 0.113462 0.816548 0.039 Uiso 1 1 calc R U . . .
C23 C 0.7738(4) 0.1338(3) 0.7971(2) 0.0265(6) Uani 1 1 d . . . . .
H23 H 0.748652 0.060486 0.734170 0.032 Uiso 1 1 calc R U . . .
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'
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'
O O 0.0106 0.0060 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Pd1 P1 80.77(9) . . ?
C2 Pd1 Cl1 94.66(9) . . ?
P1 Pd1 Cl1 175.04(3) . . ?
C2 Pd1 Cl1 175.85(9) . 2_656 ?
P1 Pd1 Cl1 98.32(3) . 2_656 ?
Cl1 Pd1 Cl1 86.38(3) . 2_656 ?
C1 Fe1 C5 41.46(12) . . ?
C1 Fe1 C8 153.45(14) . . ?
C5 Fe1 C8 163.75(15) . . ?
C1 Fe1 C6 111.68(14) . . ?
C5 Fe1 C6 117.36(16) . . ?
C8 Fe1 C6 68.30(17) . . ?
C1 Fe1 C10 130.34(15) . . ?
C5 Fe1 C10 105.66(16) . . ?
C8 Fe1 C10 68.06(18) . . ?
C6 Fe1 C10 40.42(15) . . ?
C1 Fe1 C9 166.15(15) . . ?
C5 Fe1 C9 125.42(15) . . ?
C8 Fe1 C9 40.28(17) . . ?
C6 Fe1 C9 68.13(15) . . ?
C10 Fe1 C9 40.55(16) . . ?
C1 Fe1 C4 68.32(13) . . ?
C5 Fe1 C4 40.63(14) . . ?
C8 Fe1 C4 126.58(16) . . ?
C6 Fe1 C4 148.20(16) . . ?
C10 Fe1 C4 113.63(15) . . ?
C9 Fe1 C4 104.19(15) . . ?
C1 Fe1 C7 121.64(13) . . ?
C5 Fe1 C7 152.65(15) . . ?
C8 Fe1 C7 40.63(16) . . ?
C6 Fe1 C7 40.42(17) . . ?
C10 Fe1 C7 67.84(17) . . ?
C9 Fe1 C7 67.87(15) . . ?
C4 Fe1 C7 166.72(16) . . ?
C1 Fe1 C2 40.58(12) . . ?
C5 Fe1 C2 69.42(12) . . ?
C8 Fe1 C2 118.95(15) . . ?
C6 Fe1 C2 133.47(13) . . ?
C10 Fe1 C2 170.22(15) . . ?
C9 Fe1 C2 149.18(14) . . ?
C4 Fe1 C2 68.57(12) . . ?
C7 Fe1 C2 112.39(13) . . ?
C1 Fe1 C3 68.10(12) . . ?
C5 Fe1 C3 68.71(13) . . ?
C8 Fe1 C3 107.73(15) . . ?
C6 Fe1 C3 171.21(15) . . ?
C10 Fe1 C3 146.54(14) . . ?
C9 Fe1 C3 114.35(14) . . ?
C4 Fe1 C3 40.49(12) . . ?
C7 Fe1 C3 131.62(15) . . ?
C2 Fe1 C3 40.73(11) . . ?
Pd1 Cl1 Pd1 93.61(2) . 2_656 ?
C12 P1 C18 107.10(12) . . ?
C12 P1 C11 102.93(12) . . ?
C18 P1 C11 105.69(12) . . ?
C12 P1 Pd1 117.15(10) . . ?
C18 P1 Pd1 116.10(8) . . ?
C11 P1 Pd1 106.45(9) . . ?
C2 C1 C5 109.6(3) . . ?
C2 C1 C11 117.8(2) . . ?
C5 C1 C11 131.8(3) . . ?
C2 C1 Fe1 71.32(17) . . ?
C5 C1 Fe1 69.45(19) . . ?
C11 C1 Fe1 117.7(2) . . ?
C1 C2 C3 106.6(2) . . ?
C1 C2 Pd1 125.7(2) . . ?
C3 C2 Pd1 127.5(2) . . ?
C1 C2 Fe1 68.09(16) . . ?
C3 C2 Fe1 69.75(17) . . ?
Pd1 C2 Fe1 129.61(14) . . ?
C4 C3 C2 108.1(3) . . ?
C4 C3 Fe1 69.06(18) . . ?
C2 C3 Fe1 69.52(16) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 127.0 . . ?
C5 C4 C3 108.9(3) . . ?
C5 C4 Fe1 68.82(19) . . ?
C3 C4 Fe1 70.45(18) . . ?
C5 C4 H4 125.6 . . ?
C3 C4 H4 125.6 . . ?
Fe1 C4 H4 126.8 . . ?
C4 C5 C1 106.7(3) . . ?
C4 C5 Fe1 70.5(2) . . ?
C1 C5 Fe1 69.09(18) . . ?
C4 C5 H5 126.6 . . ?
C1 C5 H5 126.6 . . ?
Fe1 C5 H5 125.3 . . ?
C10 C6 C7 108.0(3) . . ?
C10 C6 Fe1 69.9(2) . . ?
C7 C6 Fe1 70.1(2) . . ?
C10 C6 H6 126.0 . . ?
C7 C6 H6 126.0 . . ?
Fe1 C6 H6 125.6 . . ?
C6 C7 C8 107.9(3) . . ?
C6 C7 Fe1 69.5(2) . . ?
C8 C7 Fe1 69.3(2) . . ?
C6 C7 H7 126.0 . . ?
C8 C7 H7 126.0 . . ?
Fe1 C7 H7 126.7 . . ?
C9 C8 C7 108.0(4) . . ?
C9 C8 Fe1 70.1(2) . . ?
C7 C8 Fe1 70.0(2) . . ?
C9 C8 H8 126.0 . . ?
C7 C8 H8 126.0 . . ?
Fe1 C8 H8 125.5 . . ?
C8 C9 C10 108.1(3) . . ?
C8 C9 Fe1 69.7(2) . . ?
C10 C9 Fe1 69.7(2) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Fe1 C9 H9 126.3 . . ?
C6 C10 C9 108.0(4) . . ?
C6 C10 Fe1 69.7(2) . . ?
C9 C10 Fe1 69.8(2) . . ?
C6 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe1 C10 H10 126.2 . . ?
O1 C11 C1 129.3(3) . . ?
O1 C11 P1 123.1(2) . . ?
C1 C11 P1 107.55(19) . . ?
C17 C12 C13 119.9(3) . . ?
C17 C12 P1 118.6(2) . . ?
C13 C12 P1 121.3(2) . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 119.9(3) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C23 120.5(2) . . ?
C19 C18 P1 122.9(2) . . ?
C23 C18 P1 116.4(2) . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 118.9(3) . . ?
C22 C23 H23 120.5 . . ?
C18 C23 H23 120.5 . . ?
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
Pd1 C2 1.996(3) . ?
Pd1 P1 2.2070(7) . ?
Pd1 Cl1 2.3996(7) . ?
Pd1 Cl1 2.4230(7) 2_656 ?
Fe1 C1 2.026(3) . ?
Fe1 C5 2.031(3) . ?
Fe1 C8 2.046(4) . ?
Fe1 C6 2.047(4) . ?
Fe1 C10 2.050(4) . ?
Fe1 C9 2.051(4) . ?
Fe1 C4 2.053(3) . ?
Fe1 C7 2.055(4) . ?
Fe1 C2 2.068(3) . ?
Fe1 C3 2.072(3) . ?
P1 C12 1.808(3) . ?
P1 C18 1.825(2) . ?
P1 C11 1.892(3) . ?
O1 C11 1.216(3) . ?
C1 C2 1.420(4) . ?
C1 C5 1.436(4) . ?
C1 C11 1.439(4) . ?
C2 C3 1.441(4) . ?
C3 C4 1.427(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C10 1.415(5) . ?
C6 C7 1.417(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.424(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.421(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C12 C17 1.387(4) . ?
C12 C13 1.388(4) . ?
C13 C14 1.387(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.368(4) . ?
C18 C23 1.414(4) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
