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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/7/70/69/7706932.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_7706932
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 Br2 Fe2 O2 P2 Pd2, C7 H8'
_chemical_formula_sum            'C53 H44 Br2 Fe2 O2 P2 Pd2'
_chemical_formula_weight         1259.14
_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                108.735(2)
_cell_angle_beta                 95.248(2)
_cell_angle_gamma                97.272(2)
_cell_formula_units_Z            1
_cell_length_a                   8.6520(4)
_cell_length_b                   9.9950(4)
_cell_length_c                   14.4343(6)
_cell_measurement_reflns_used    9216
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.96
_cell_volume                     1160.93(9)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.12'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'PLATON (Spek, 2017)'
_computing_publication_material  'PLATON (Spek, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo with PHOTON III'
_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  0.0206
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       -18
_diffrn_reflns_number            25301
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.182
_exptl_absorpt_coefficient_mu    3.206
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS area'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_description       plate
_exptl_crystal_F_000             622
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.806
_refine_diff_density_min         -1.852
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0335
_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)+(0.0312P)²+3.8691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4872
_reflns_number_total             5317
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt00668a3.cif
_cod_data_source_block           pv448_sq
_cod_depositor_comments
'Adding full bibliography for 7706929--7706948.cif.'
_cod_database_code               7706932
_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   0.513
_shelx_estimated_absorpt_t_max   0.761
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 0.46456(3) 0.13588(2) 0.61216(2) 0.02351(8) Uani 1 1 d . . . . .
Br1 Br 0.49084(6) 0.12220(4) 0.43752(3) 0.04367(12) Uani 1 1 d . . . . .
Fe1 Fe 0.54395(6) 0.52950(5) 0.72556(4) 0.03007(12) Uani 1 1 d . . . . .
P1 P 0.45736(10) 0.17280(8) 0.77108(6) 0.02180(16) Uani 1 1 d . . . . .
O1 O 0.3279(3) 0.3797(3) 0.90169(18) 0.0313(5) Uani 1 1 d . . . . .
C1 C 0.3544(4) 0.4025(3) 0.7428(3) 0.0271(7) Uani 1 1 d . . . . .
C2 C 0.4072(4) 0.3325(3) 0.6514(3) 0.0265(7) Uani 1 1 d . . . . .
C3 C 0.3971(5) 0.4255(4) 0.5940(3) 0.0319(7) Uani 1 1 d . . . . .
H3 H 0.424329 0.407186 0.529334 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3399(5) 0.5493(4) 0.6498(3) 0.0371(8) Uani 1 1 d . . . . .
H4 H 0.321534 0.627055 0.628379 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3146(5) 0.5377(4) 0.7431(3) 0.0345(8) Uani 1 1 d . . . . .
H5 H 0.278447 0.606126 0.795491 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7689(5) 0.5127(5) 0.7750(4) 0.0473(11) Uani 1 1 d . . . . .
H6 H 0.805098 0.428170 0.777981 0.057 Uiso 1 1 calc R U . . .
C7 C 0.7681(5) 0.5632(5) 0.6933(4) 0.0488(10) Uani 1 1 d . . . . .
H7 H 0.802098 0.517604 0.631912 0.059 Uiso 1 1 calc R U . . .
C8 C 0.7080(5) 0.6924(5) 0.7199(4) 0.0485(11) Uani 1 1 d . . . . .
H8 H 0.695300 0.750178 0.679639 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6697(6) 0.7216(5) 0.8168(4) 0.0520(11) Uani 1 1 d . . . . .
H9 H 0.626658 0.802191 0.852987 0.062 Uiso 1 1 calc R U . . .
C10 C 0.7068(5) 0.6097(5) 0.8504(3) 0.0487(11) Uani 1 1 d . . . . .
H10 H 0.692334 0.601513 0.912976 0.058 Uiso 1 1 calc R U . . .
C11 C 0.3680(4) 0.3404(3) 0.8202(2) 0.0240(6) Uani 1 1 d . . . . .
C12 C 0.3329(4) 0.0413(3) 0.8051(3) 0.0263(6) Uani 1 1 d . . . . .
C13 C 0.3404(5) 0.0453(4) 0.9020(3) 0.0369(8) Uani 1 1 d . . . . .
H13 H 0.418624 0.111824 0.951451 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2324(5) -0.0490(5) 0.9269(3) 0.0443(10) Uani 1 1 d . . . . .
H14 H 0.236325 -0.046026 0.993567 0.053 Uiso 1 1 calc R U . . .
C15 C 0.1198(5) -0.1466(4) 0.8547(3) 0.0406(9) Uani 1 1 d . . . . .
H15 H 0.045775 -0.210229 0.871857 0.049 Uiso 1 1 calc R U . . .
C16 C 0.1144(5) -0.1521(4) 0.7581(3) 0.0398(9) Uani 1 1 d . . . . .
H16 H 0.037712 -0.220524 0.708562 0.048 Uiso 1 1 calc R U . . .
C17 C 0.2204(4) -0.0583(4) 0.7325(3) 0.0344(8) Uani 1 1 d . . . . .
H17 H 0.216111 -0.062003 0.665693 0.041 Uiso 1 1 calc R U . . .
C18 C 0.6505(3) 0.2108(3) 0.8468(2) 0.0180(5) Uani 1 1 d . . . . .
C19 C 0.6873(4) 0.3163(3) 0.9365(2) 0.0255(6) Uani 1 1 d . . . . .
H19 H 0.608451 0.366754 0.965842 0.031 Uiso 1 1 calc R U . . .
C20 C 0.8405(4) 0.3498(4) 0.9849(3) 0.0300(7) Uani 1 1 d . . . . .
H20 H 0.867067 0.424291 1.047053 0.036 Uiso 1 1 calc R U . . .
C21 C 0.9542(4) 0.2747(4) 0.9427(3) 0.0343(8) Uani 1 1 d . . . . .
H21 H 1.059192 0.298332 0.975780 0.041 Uiso 1 1 calc R U . . .
C22 C 0.9166(5) 0.1659(4) 0.8529(3) 0.0382(8) Uani 1 1 d . . . . .
H22 H 0.995176 0.113577 0.824981 0.046 Uiso 1 1 calc R U . . .
C23 C 0.7652(4) 0.1326(4) 0.8035(3) 0.0327(7) Uani 1 1 d . . . . .
H23 H 0.738763 0.058154 0.741323 0.039 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'
Br Br -0.2901 2.4595 '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 81.08(10) . . ?
C2 Pd1 Br1 94.39(10) . . ?
P1 Pd1 Br1 173.45(3) . . ?
C2 Pd1 Br1 174.40(10) . 2_656 ?
P1 Pd1 Br1 97.77(2) . 2_656 ?
Br1 Pd1 Br1 87.186(14) . 2_656 ?
Pd1 Br1 Pd1 92.814(14) . 2_656 ?
C1 Fe1 C5 41.37(13) . . ?
C1 Fe1 C9 131.76(18) . . ?
C5 Fe1 C9 106.41(19) . . ?
C1 Fe1 C7 152.19(17) . . ?
C5 Fe1 C7 165.07(17) . . ?
C9 Fe1 C7 67.8(2) . . ?
C1 Fe1 C8 167.62(18) . . ?
C5 Fe1 C8 126.73(18) . . ?
C9 Fe1 C8 40.4(2) . . ?
C7 Fe1 C8 40.1(2) . . ?
C1 Fe1 C10 112.32(16) . . ?
C5 Fe1 C10 117.23(19) . . ?
C9 Fe1 C10 40.41(19) . . ?
C7 Fe1 C10 68.0(2) . . ?
C8 Fe1 C10 67.92(18) . . ?
C1 Fe1 C4 68.25(15) . . ?
C5 Fe1 C4 40.73(16) . . ?
C9 Fe1 C4 113.36(18) . . ?
C7 Fe1 C4 127.40(18) . . ?
C8 Fe1 C4 104.59(17) . . ?
C10 Fe1 C4 147.64(19) . . ?
C1 Fe1 C6 121.14(15) . . ?
C5 Fe1 C6 151.64(18) . . ?
C9 Fe1 C6 67.5(2) . . ?
C7 Fe1 C6 40.56(18) . . ?
C8 Fe1 C6 67.61(17) . . ?
C10 Fe1 C6 40.0(2) . . ?
C4 Fe1 C6 167.63(18) . . ?
C1 Fe1 C2 40.84(14) . . ?
C5 Fe1 C2 69.68(14) . . ?
C9 Fe1 C2 171.95(18) . . ?
C7 Fe1 C2 117.75(17) . . ?
C8 Fe1 C2 147.56(18) . . ?
C10 Fe1 C2 134.39(16) . . ?
C4 Fe1 C2 68.62(14) . . ?
C6 Fe1 C2 112.39(16) . . ?
C1 Fe1 C3 68.05(15) . . ?
C5 Fe1 C3 68.66(16) . . ?
C9 Fe1 C3 145.37(17) . . ?
C7 Fe1 C3 107.77(18) . . ?
C8 Fe1 C3 113.56(17) . . ?
C10 Fe1 C3 172.05(18) . . ?
C4 Fe1 C3 40.29(14) . . ?
C6 Fe1 C3 132.51(18) . . ?
C2 Fe1 C3 40.74(13) . . ?
C12 P1 C18 107.45(14) . . ?
C12 P1 C11 103.19(15) . . ?
C18 P1 C11 105.07(14) . . ?
C12 P1 Pd1 118.12(12) . . ?
C18 P1 Pd1 115.00(10) . . ?
C11 P1 Pd1 106.56(11) . . ?
C2 C1 C5 109.6(3) . . ?
C2 C1 C11 118.5(3) . . ?
C5 C1 C11 131.3(3) . . ?
C2 C1 Fe1 70.8(2) . . ?
C5 C1 Fe1 69.4(2) . . ?
C11 C1 Fe1 119.3(2) . . ?
C1 C2 C3 106.2(3) . . ?
C1 C2 Pd1 124.8(2) . . ?
C3 C2 Pd1 128.8(3) . . ?
C1 C2 Fe1 68.37(18) . . ?
C3 C2 Fe1 69.7(2) . . ?
Pd1 C2 Fe1 130.35(17) . . ?
C4 C3 C2 108.8(3) . . ?
C4 C3 Fe1 69.6(2) . . ?
C2 C3 Fe1 69.55(19) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
Fe1 C3 H3 126.8 . . ?
C3 C4 C5 108.7(3) . . ?
C3 C4 Fe1 70.1(2) . . ?
C5 C4 Fe1 68.7(2) . . ?
C3 C4 H4 125.6 . . ?
C5 C4 H4 125.6 . . ?
Fe1 C4 H4 127.1 . . ?
C4 C5 C1 106.6(3) . . ?
C4 C5 Fe1 70.5(2) . . ?
C1 C5 Fe1 69.2(2) . . ?
C4 C5 H5 126.7 . . ?
C1 C5 H5 126.7 . . ?
Fe1 C5 H5 125.2 . . ?
C10 C6 C7 108.2(4) . . ?
C10 C6 Fe1 69.7(3) . . ?
C7 C6 Fe1 69.4(2) . . ?
C10 C6 H6 125.9 . . ?
C7 C6 H6 125.9 . . ?
Fe1 C6 H6 126.6 . . ?
C8 C7 C6 107.7(4) . . ?
C8 C7 Fe1 70.0(3) . . ?
C6 C7 Fe1 70.1(2) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
Fe1 C7 H7 125.4 . . ?
C7 C8 C9 108.2(4) . . ?
C7 C8 Fe1 69.9(2) . . ?
C9 C8 Fe1 69.7(2) . . ?
C7 C8 H8 125.9 . . ?
C9 C8 H8 125.9 . . ?
Fe1 C8 H8 126.0 . . ?
C8 C9 C10 108.0(4) . . ?
C8 C9 Fe1 69.9(2) . . ?
C10 C9 Fe1 69.9(2) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Fe1 C9 H9 125.9 . . ?
C6 C10 C9 107.9(4) . . ?
C6 C10 Fe1 70.3(3) . . ?
C9 C10 Fe1 69.7(2) . . ?
C6 C10 H10 126.1 . . ?
C9 C10 H10 126.1 . . ?
Fe1 C10 H10 125.5 . . ?
O1 C11 C1 129.4(3) . . ?
O1 C11 P1 123.2(3) . . ?
C1 C11 P1 107.3(2) . . ?
C13 C12 C17 120.1(3) . . ?
C13 C12 P1 121.3(3) . . ?
C17 C12 P1 118.4(3) . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 119.7(4) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
C19 C18 C23 120.8(3) . . ?
C19 C18 P1 122.8(2) . . ?
C23 C18 P1 116.2(2) . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.5(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 120.6 . . ?
C18 C23 H23 120.6 . . ?
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 2.003(3) . ?
Pd1 P1 2.2114(8) . ?
Pd1 Br1 2.5132(4) . ?
Pd1 Br1 2.5361(4) 2_656 ?
Fe1 C1 2.028(4) . ?
Fe1 C5 2.032(4) . ?
Fe1 C9 2.047(4) . ?
Fe1 C7 2.047(4) . ?
Fe1 C8 2.048(4) . ?
Fe1 C10 2.049(4) . ?
Fe1 C4 2.055(4) . ?
Fe1 C6 2.057(4) . ?
Fe1 C2 2.061(3) . ?
Fe1 C3 2.063(4) . ?
P1 C12 1.811(3) . ?
P1 C18 1.836(3) . ?
P1 C11 1.890(3) . ?
O1 C11 1.212(4) . ?
C1 C2 1.427(5) . ?
C1 C5 1.434(5) . ?
C1 C11 1.445(5) . ?
C2 C3 1.435(5) . ?
C3 C4 1.418(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.423(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C10 1.405(7) . ?
C6 C7 1.423(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.414(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.414(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C12 C13 1.382(5) . ?
C12 C17 1.392(5) . ?
C13 C14 1.394(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.360(4) . ?
C18 C23 1.409(4) . ?
C19 C20 1.387(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
