#------------------------------------------------------------------------------
#$Date: 2020-11-06 13:41:39 +0100 (vie 06 de nov de 2020) $
#$Revision: 258891 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/99/7059964.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_7059964
loop_
_publ_author_name
'Kadari, Lingaswamy'
'Erb, William'
'Roisnel, Thierry'
'Radha Krishna, Palakodety'
'Mongin, Florence'
_publ_section_title
;
 Iodoferrocene as a partner in N-arylation of amides
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15928
_journal_page_last               15941
_journal_paper_doi               10.1039/D0NJ03470C
_journal_volume                  44
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H16 Cl Fe N O'
_chemical_formula_sum            'C18 H16 Cl Fe N O'
_chemical_formula_weight         353.62
_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     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-07-07 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                109.852(3)
_cell_angle_beta                 100.413(3)
_cell_angle_gamma                91.180(4)
_cell_formula_units_Z            4
_cell_length_a                   10.3749(11)
_cell_length_b                   11.6955(13)
_cell_length_c                   13.3758(12)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.5420
_cell_measurement_theta_min      2.3287
_cell_measurement_wavelength     0.710730
_cell_volume                     1495.5(3)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0190262
_diffrn_orient_matrix_UB_12      0.0898840
_diffrn_orient_matrix_UB_13      0.0191385
_diffrn_orient_matrix_UB_21      0.0820114
_diffrn_orient_matrix_UB_22      -0.0147273
_diffrn_orient_matrix_UB_23      -0.0302116
_diffrn_orient_matrix_UB_31      -0.0509135
_diffrn_orient_matrix_UB_32      -0.0057626
_diffrn_orient_matrix_UB_33      -0.0728092
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29628
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_min         2.329
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.187
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_refine_diff_density_max         1.594
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0424P)²+2.5530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6090
_reflns_number_total             6806
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0nj03470c2.cif
_cod_data_source_block           WE9512
_cod_depositor_comments
'Adding full bibliography for 7059953--7059970.cif.'
_cod_database_code               7059964
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
Fe1 Fe 0.43316(3) 0.64032(3) 0.21038(2) 0.01470(9) Uani 1 1 d . . . . .
Cl1 Cl 0.40142(7) 1.12157(6) 0.06727(5) 0.03170(15) Uani 1 1 d . . . . .
C1 C 0.4429(2) 0.4563(2) 0.1447(2) 0.0231(5) Uani 1 1 d . . . . .
H1 H 0.427141 0.409644 0.069356 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3469(2) 0.4811(2) 0.2115(2) 0.0235(5) Uani 1 1 d . . . . .
H2 H 0.256069 0.453608 0.188593 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4108(3) 0.5540(2) 0.3181(2) 0.0248(5) Uani 1 1 d . . . . .
H3 H 0.370326 0.583970 0.379218 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5465(3) 0.5745(2) 0.3174(2) 0.0254(5) Uani 1 1 d . . . . .
H4 H 0.612257 0.620820 0.378021 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5663(2) 0.5137(2) 0.2105(2) 0.0244(5) Uani 1 1 d . . . . .
H5 H 0.647599 0.511745 0.187059 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4993(2) 0.81857(19) 0.24712(18) 0.0166(4) Uani 1 1 d . . . . .
H6 H 0.569774 0.862540 0.304565 0.020 Uiso 1 1 calc R U . . .
C7 C 0.5093(2) 0.7485(2) 0.13929(19) 0.0204(5) Uani 1 1 d . . . . .
H7 H 0.587938 0.739078 0.111473 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3817(2) 0.6947(2) 0.07990(19) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.360893 0.642525 0.006068 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2903(2) 0.7325(2) 0.15013(18) 0.0198(4) Uani 1 1 d . . . . .
H9 H 0.198193 0.710099 0.132023 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3636(2) 0.81058(19) 0.25305(18) 0.0158(4) Uani 1 1 d . . . . .
N11 N 0.30963(18) 0.87843(17) 0.34339(15) 0.0167(4) Uani 1 1 d . . . . .
C12 C 0.2120(2) 0.8157(2) 0.3779(2) 0.0202(4) Uani 1 1 d . . . . .
H12A H 0.257078 0.773620 0.424482 0.030 Uiso 1 1 calc R U . . .
H12B H 0.155274 0.755987 0.314021 0.030 Uiso 1 1 calc R U . . .
H12C H 0.158290 0.875452 0.418447 0.030 Uiso 1 1 calc R U . . .
C13 C 0.3435(2) 0.9999(2) 0.39950(18) 0.0170(4) Uani 1 1 d . . . . .
O14 O 0.31135(18) 1.05121(16) 0.48691(14) 0.0258(4) Uani 1 1 d . . . . .
C15 C 0.4142(2) 1.07501(19) 0.35068(19) 0.0165(4) Uani 1 1 d . . . . .
C16 C 0.5020(2) 1.1728(2) 0.4217(2) 0.0206(4) Uani 1 1 d . . . . .
H16 H 0.521490 1.185106 0.497031 0.025 Uiso 1 1 calc R U . . .
C17 C 0.5615(2) 1.2525(2) 0.3825(2) 0.0226(5) Uani 1 1 d . . . . .
H17 H 0.622974 1.317637 0.430989 0.027 Uiso 1 1 calc R U . . .
C18 C 0.5314(2) 1.2370(2) 0.2737(2) 0.0226(5) Uani 1 1 d . . . . .
H18 H 0.570727 1.291695 0.246791 0.027 Uiso 1 1 calc R U . . .
C19 C 0.4430(2) 1.1405(2) 0.20443(18) 0.0194(4) Uani 1 1 d . . . . .
C20 C 0.3849(2) 1.0581(2) 0.24072(19) 0.0183(4) Uani 1 1 d . . . . .
H20 H 0.326063 0.991413 0.191285 0.022 Uiso 1 1 calc R U . . .
Fe2 Fe 0.08207(3) 0.87135(3) 0.79103(2) 0.01613(9) Uani 1 1 d . . . . .
Cl2 Cl 0.13077(7) 0.39404(6) 0.94072(5) 0.03329(15) Uani 1 1 d . . . . .
C51 C 0.1534(3) 0.9342(2) 0.6838(2) 0.0280(5) Uani 1 1 d . . . . .
H51 H 0.194664 0.888016 0.626962 0.034 Uiso 1 1 calc R U . . .
C52 C 0.2176(2) 1.0012(2) 0.7922(2) 0.0255(5) Uani 1 1 d . . . . .
H52 H 0.309374 1.007730 0.820496 0.031 Uiso 1 1 calc R U . . .
C53 C 0.1205(3) 1.0568(2) 0.8509(2) 0.0251(5) Uani 1 1 d . . . . .
H53 H 0.135668 1.106708 0.925425 0.030 Uiso 1 1 calc R U . . .
C54 C -0.0038(2) 1.0242(2) 0.7780(2) 0.0242(5) Uani 1 1 d . . . . .
H54 H -0.086053 1.049267 0.795342 0.029 Uiso 1 1 calc R U . . .
C55 C 0.0164(3) 0.9482(2) 0.6753(2) 0.0259(5) Uani 1 1 d . . . . .
H55 H -0.049856 0.912777 0.611922 0.031 Uiso 1 1 calc R U . . .
C56 C -0.0337(2) 0.7782(2) 0.85333(19) 0.0232(5) Uani 1 1 d . . . . .
H56 H -0.117648 0.797695 0.869716 0.028 Uiso 1 1 calc R U . . .
C57 C 0.0908(3) 0.8229(2) 0.9246(2) 0.0281(5) Uani 1 1 d . . . . .
H57 H 0.104014 0.877385 0.997508 0.034 Uiso 1 1 calc R U . . .
C58 C 0.1919(2) 0.7724(2) 0.8682(2) 0.0256(5) Uani 1 1 d . . . . .
H58 H 0.283704 0.786804 0.897197 0.031 Uiso 1 1 calc R U . . .
C59 C 0.1317(2) 0.6965(2) 0.7608(2) 0.0201(4) Uani 1 1 d . . . . .
H59 H 0.175813 0.652759 0.704948 0.024 Uiso 1 1 calc R U . . .
C60 C -0.0078(2) 0.6985(2) 0.75266(19) 0.0174(4) Uani 1 1 d . . . . .
N61 N -0.10441(18) 0.62693(17) 0.66217(16) 0.0174(4) Uani 1 1 d . . . . .
C62 C -0.2192(2) 0.6847(2) 0.6262(2) 0.0209(5) Uani 1 1 d . . . . .
H62A H -0.189781 0.754876 0.609282 0.031 Uiso 1 1 calc R U . . .
H62B H -0.269642 0.712124 0.684116 0.031 Uiso 1 1 calc R U . . .
H62C H -0.274944 0.625549 0.561334 0.031 Uiso 1 1 calc R U . . .
C63 C -0.0982(2) 0.5056(2) 0.60720(18) 0.0178(4) Uani 1 1 d . . . . .
O64 O -0.17306(17) 0.45205(16) 0.51998(15) 0.0266(4) Uani 1 1 d . . . . .
C65 C -0.0039(2) 0.4343(2) 0.65641(19) 0.0171(4) Uani 1 1 d . . . . .
C66 C 0.0460(2) 0.3370(2) 0.58469(19) 0.0200(4) Uani 1 1 d . . . . .
H66 H 0.026666 0.323647 0.509202 0.024 Uiso 1 1 calc R U . . .
C67 C 0.1239(2) 0.2595(2) 0.6228(2) 0.0221(5) Uani 1 1 d . . . . .
H67 H 0.159569 0.194887 0.573663 0.027 Uiso 1 1 calc R U . . .
C68 C 0.1497(2) 0.2763(2) 0.7325(2) 0.0216(5) Uani 1 1 d . . . . .
H68 H 0.201976 0.222947 0.758888 0.026 Uiso 1 1 calc R U . . .
C69 C 0.0984(2) 0.3715(2) 0.80246(18) 0.0187(4) Uani 1 1 d . . . . .
C70 C 0.0224(2) 0.4523(2) 0.76686(19) 0.0179(4) Uani 1 1 d . . . . .
H70 H -0.010767 0.518127 0.816789 0.021 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'
N N 0.0061 0.0033 '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'
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
C8 Fe1 C1 104.62(10) . . ?
C8 Fe1 C7 40.79(10) . . ?
C1 Fe1 C7 117.84(10) . . ?
C8 Fe1 C6 68.81(9) . . ?
C1 Fe1 C6 153.63(9) . . ?
C7 Fe1 C6 40.66(9) . . ?
C8 Fe1 C5 121.13(10) . . ?
C1 Fe1 C5 40.69(10) . . ?
C7 Fe1 C5 104.38(10) . . ?
C6 Fe1 C5 119.40(9) . . ?
C8 Fe1 C4 158.64(11) . . ?
C1 Fe1 C4 68.31(10) . . ?
C7 Fe1 C4 123.15(10) . . ?
C6 Fe1 C4 108.08(9) . . ?
C5 Fe1 C4 40.56(10) . . ?
C8 Fe1 C2 120.50(10) . . ?
C1 Fe1 C2 40.72(9) . . ?
C7 Fe1 C2 154.38(10) . . ?
C6 Fe1 C2 164.31(9) . . ?
C5 Fe1 C2 68.33(10) . . ?
C4 Fe1 C2 68.10(10) . . ?
C8 Fe1 C9 40.72(9) . . ?
C1 Fe1 C9 123.47(10) . . ?
C7 Fe1 C9 68.59(9) . . ?
C6 Fe1 C9 69.05(9) . . ?
C5 Fe1 C9 158.83(10) . . ?
C4 Fe1 C9 159.71(10) . . ?
C2 Fe1 C9 108.93(10) . . ?
C8 Fe1 C10 68.06(9) . . ?
C1 Fe1 C10 162.30(10) . . ?
C7 Fe1 C10 67.88(9) . . ?
C6 Fe1 C10 40.67(8) . . ?
C5 Fe1 C10 156.93(9) . . ?
C4 Fe1 C10 124.23(9) . . ?
C2 Fe1 C10 127.88(9) . . ?
C9 Fe1 C10 40.66(9) . . ?
C8 Fe1 C3 157.41(11) . . ?
C1 Fe1 C3 68.22(10) . . ?
C7 Fe1 C3 161.68(10) . . ?
C6 Fe1 C3 127.06(9) . . ?
C5 Fe1 C3 68.24(10) . . ?
C4 Fe1 C3 40.57(10) . . ?
C2 Fe1 C3 40.29(10) . . ?
C9 Fe1 C3 124.18(10) . . ?
C10 Fe1 C3 112.01(9) . . ?
C5 C1 C2 108.0(2) . . ?
C5 C1 Fe1 69.78(13) . . ?
C2 C1 Fe1 70.11(13) . . ?
C5 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
Fe1 C1 H1 125.7 . . ?
C3 C2 C1 108.1(2) . . ?
C3 C2 Fe1 70.09(13) . . ?
C1 C2 Fe1 69.16(13) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 126.3 . . ?
C2 C3 C4 107.9(2) . . ?
C2 C3 Fe1 69.62(14) . . ?
C4 C3 Fe1 69.30(14) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
Fe1 C3 H3 126.6 . . ?
C5 C4 C3 108.1(2) . . ?
C5 C4 Fe1 69.55(14) . . ?
C3 C4 Fe1 70.13(14) . . ?
C5 C4 H4 125.9 . . ?
C3 C4 H4 125.9 . . ?
Fe1 C4 H4 126.0 . . ?
C4 C5 C1 107.9(2) . . ?
C4 C5 Fe1 69.89(14) . . ?
C1 C5 Fe1 69.52(14) . . ?
C4 C5 H5 126.0 . . ?
C1 C5 H5 126.0 . . ?
Fe1 C5 H5 126.1 . . ?
C7 C6 C10 107.19(19) . . ?
C7 C6 Fe1 69.61(13) . . ?
C10 C6 Fe1 70.27(12) . . ?
C7 C6 H6 126.4 . . ?
C10 C6 H6 126.4 . . ?
Fe1 C6 H6 125.3 . . ?
C6 C7 C8 108.6(2) . . ?
C6 C7 Fe1 69.73(12) . . ?
C8 C7 Fe1 69.53(13) . . ?
C6 C7 H7 125.7 . . ?
C8 C7 H7 125.7 . . ?
Fe1 C7 H7 126.6 . . ?
C7 C8 C9 108.4(2) . . ?
C7 C8 Fe1 69.68(13) . . ?
C9 C8 Fe1 70.26(13) . . ?
C7 C8 H8 125.8 . . ?
C9 C8 H8 125.8 . . ?
Fe1 C8 H8 125.8 . . ?
C8 C9 C10 106.9(2) . . ?
C8 C9 Fe1 69.02(13) . . ?
C10 C9 Fe1 69.79(12) . . ?
C8 C9 H9 126.5 . . ?
C10 C9 H9 126.5 . . ?
Fe1 C9 H9 126.2 . . ?
N11 C10 C6 125.1(2) . . ?
N11 C10 C9 125.8(2) . . ?
C6 C10 C9 108.91(19) . . ?
N11 C10 Fe1 131.88(15) . . ?
C6 C10 Fe1 69.06(12) . . ?
C9 C10 Fe1 69.55(12) . . ?
C13 N11 C10 123.23(18) . . ?
C13 N11 C12 118.15(18) . . ?
C10 N11 C12 118.62(18) . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O14 C13 N11 121.3(2) . . ?
O14 C13 C15 118.8(2) . . ?
N11 C13 C15 119.72(19) . . ?
C20 C15 C16 119.7(2) . . ?
C20 C15 C13 122.5(2) . . ?
C16 C15 C13 117.5(2) . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 118.8(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C20 122.1(2) . . ?
C18 C19 Cl1 119.38(18) . . ?
C20 C19 Cl1 118.49(18) . . ?
C19 C20 C15 118.8(2) . . ?
C19 C20 H20 120.6 . . ?
C15 C20 H20 120.6 . . ?
C58 Fe2 C57 40.92(11) . . ?
C58 Fe2 C59 40.89(10) . . ?
C57 Fe2 C59 68.94(10) . . ?
C58 Fe2 C52 102.97(10) . . ?
C57 Fe2 C52 119.72(11) . . ?
C59 Fe2 C52 119.03(10) . . ?
C58 Fe2 C53 118.06(10) . . ?
C57 Fe2 C53 104.81(11) . . ?
C59 Fe2 C53 154.10(10) . . ?
C52 Fe2 C53 40.74(10) . . ?
C58 Fe2 C51 120.96(11) . . ?
C57 Fe2 C51 156.57(12) . . ?
C59 Fe2 C51 106.99(10) . . ?
C52 Fe2 C51 40.57(11) . . ?
C53 Fe2 C51 68.29(10) . . ?
C58 Fe2 C54 155.69(11) . . ?
C57 Fe2 C54 122.35(11) . . ?
C59 Fe2 C54 163.21(10) . . ?
C52 Fe2 C54 68.20(10) . . ?
C53 Fe2 C54 40.66(10) . . ?
C51 Fe2 C54 67.83(10) . . ?
C58 Fe2 C56 68.88(10) . . ?
C57 Fe2 C56 40.77(10) . . ?
C59 Fe2 C56 69.16(10) . . ?
C52 Fe2 C56 157.64(11) . . ?
C53 Fe2 C56 123.34(10) . . ?
C51 Fe2 C56 161.29(11) . . ?
C54 Fe2 C56 110.30(10) . . ?
C58 Fe2 C55 159.32(11) . . ?
C57 Fe2 C55 159.72(11) . . ?
C59 Fe2 C55 125.71(10) . . ?
C52 Fe2 C55 68.18(10) . . ?
C53 Fe2 C55 68.18(10) . . ?
C51 Fe2 C55 40.42(11) . . ?
C54 Fe2 C55 40.16(10) . . ?
C56 Fe2 C55 126.08(11) . . ?
C58 Fe2 C60 68.22(9) . . ?
C57 Fe2 C60 68.04(10) . . ?
C59 Fe2 C60 40.85(9) . . ?
C52 Fe2 C60 157.37(10) . . ?
C53 Fe2 C60 161.85(10) . . ?
C51 Fe2 C60 124.85(10) . . ?
C54 Fe2 C60 127.97(10) . . ?
C56 Fe2 C60 40.53(9) . . ?
C55 Fe2 C60 112.47(10) . . ?
C52 C51 C55 108.1(2) . . ?
C52 C51 Fe2 69.28(14) . . ?
C55 C51 Fe2 70.13(14) . . ?
C52 C51 H51 126.0 . . ?
C55 C51 H51 126.0 . . ?
Fe2 C51 H51 126.2 . . ?
C51 C52 C53 108.0(2) . . ?
C51 C52 Fe2 70.15(14) . . ?
C53 C52 Fe2 69.65(14) . . ?
C51 C52 H52 126.0 . . ?
C53 C52 H52 126.0 . . ?
Fe2 C52 H52 125.8 . . ?
C52 C53 C54 107.7(2) . . ?
C52 C53 Fe2 69.61(14) . . ?
C54 C53 Fe2 70.31(13) . . ?
C52 C53 H53 126.1 . . ?
C54 C53 H53 126.1 . . ?
Fe2 C53 H53 125.5 . . ?
C55 C54 C53 108.2(2) . . ?
C55 C54 Fe2 70.03(14) . . ?
C53 C54 Fe2 69.03(14) . . ?
C55 C54 H54 125.9 . . ?
C53 C54 H54 125.9 . . ?
Fe2 C54 H54 126.6 . . ?
C54 C55 C51 108.0(2) . . ?
C54 C55 Fe2 69.81(14) . . ?
C51 C55 Fe2 69.45(14) . . ?
C54 C55 H55 126.0 . . ?
C51 C55 H55 126.0 . . ?
Fe2 C55 H55 126.3 . . ?
C57 C56 C60 106.9(2) . . ?
C57 C56 Fe2 68.72(14) . . ?
C60 C56 Fe2 69.89(13) . . ?
C57 C56 H56 126.5 . . ?
C60 C56 H56 126.5 . . ?
Fe2 C56 H56 126.4 . . ?
C58 C57 C56 108.7(2) . . ?
C58 C57 Fe2 69.47(14) . . ?
C56 C57 Fe2 70.51(14) . . ?
C58 C57 H57 125.7 . . ?
C56 C57 H57 125.7 . . ?
Fe2 C57 H57 125.9 . . ?
C57 C58 C59 108.3(2) . . ?
C57 C58 Fe2 69.61(14) . . ?
C59 C58 Fe2 69.78(13) . . ?
C57 C58 H58 125.8 . . ?
C59 C58 H58 125.8 . . ?
Fe2 C58 H58 126.3 . . ?
C58 C59 C60 107.2(2) . . ?
C58 C59 Fe2 69.33(13) . . ?
C60 C59 Fe2 70.46(13) . . ?
C58 C59 H59 126.4 . . ?
C60 C59 H59 126.4 . . ?
Fe2 C59 H59 125.4 . . ?
N61 C60 C56 125.5(2) . . ?
N61 C60 C59 125.5(2) . . ?
C56 C60 C59 108.9(2) . . ?
N61 C60 Fe2 130.91(16) . . ?
C56 C60 Fe2 69.58(13) . . ?
C59 C60 Fe2 68.69(12) . . ?
C63 N61 C60 123.63(18) . . ?
C63 N61 C62 117.71(19) . . ?
C60 N61 C62 118.65(18) . . ?
N61 C62 H62A 109.5 . . ?
N61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
N61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
O64 C63 N61 121.0(2) . . ?
O64 C63 C65 119.0(2) . . ?
N61 C63 C65 119.9(2) . . ?
C70 C65 C66 119.6(2) . . ?
C70 C65 C63 123.1(2) . . ?
C66 C65 C63 116.8(2) . . ?
C67 C66 C65 120.5(2) . . ?
C67 C66 H66 119.7 . . ?
C65 C66 H66 119.7 . . ?
C68 C67 C66 120.1(2) . . ?
C68 C67 H67 119.9 . . ?
C66 C67 H67 119.9 . . ?
C69 C68 C67 119.0(2) . . ?
C69 C68 H68 120.5 . . ?
C67 C68 H68 120.5 . . ?
C68 C69 C70 122.2(2) . . ?
C68 C69 Cl2 119.41(18) . . ?
C70 C69 Cl2 118.42(18) . . ?
C69 C70 C65 118.6(2) . . ?
C69 C70 H70 120.7 . . ?
C65 C70 H70 120.7 . . ?
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
Fe1 C8 2.041(2) . ?
Fe1 C1 2.042(2) . ?
Fe1 C7 2.043(2) . ?
Fe1 C6 2.045(2) . ?
Fe1 C5 2.045(2) . ?
Fe1 C4 2.050(2) . ?
Fe1 C2 2.055(2) . ?
Fe1 C9 2.058(2) . ?
Fe1 C10 2.061(2) . ?
Fe1 C3 2.061(2) . ?
Cl1 C19 1.742(2) . ?
C1 C5 1.421(3) . ?
C1 C2 1.425(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.420(3) . ?
C6 C10 1.427(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.423(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.426(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.431(3) . ?
C9 H9 0.9500 . ?
C10 N11 1.420(3) . ?
N11 C13 1.365(3) . ?
N11 C12 1.466(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O14 1.229(3) . ?
C13 C15 1.508(3) . ?
C15 C20 1.390(3) . ?
C15 C16 1.395(3) . ?
C16 C17 1.397(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9500 . ?
Fe2 C58 2.035(2) . ?
Fe2 C57 2.037(2) . ?
Fe2 C59 2.041(2) . ?
Fe2 C52 2.042(2) . ?
Fe2 C53 2.043(2) . ?
Fe2 C51 2.054(2) . ?
Fe2 C54 2.060(2) . ?
Fe2 C56 2.061(2) . ?
Fe2 C55 2.063(2) . ?
Fe2 C60 2.065(2) . ?
Cl2 C69 1.744(2) . ?
C51 C52 1.420(4) . ?
C51 C55 1.422(4) . ?
C51 H51 0.9500 . ?
C52 C53 1.422(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.426(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.415(4) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 C57 1.428(4) . ?
C56 C60 1.429(3) . ?
C56 H56 0.9500 . ?
C57 C58 1.423(4) . ?
C57 H57 0.9500 . ?
C58 C59 1.424(4) . ?
C58 H58 0.9500 . ?
C59 C60 1.433(3) . ?
C59 H59 0.9500 . ?
C60 N61 1.417(3) . ?
N61 C63 1.367(3) . ?
N61 C62 1.467(3) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C63 O64 1.230(3) . ?
C63 C65 1.503(3) . ?
C65 C70 1.394(3) . ?
C65 C66 1.395(3) . ?
C66 C67 1.389(3) . ?
C66 H66 0.9500 . ?
C67 C68 1.386(4) . ?
C67 H67 0.9500 . ?
C68 C69 1.377(3) . ?
C68 H68 0.9500 . ?
C69 C70 1.393(3) . ?
C70 H70 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 0.3(3) . . . . ?
Fe1 C1 C2 C3 -59.51(17) . . . . ?
C5 C1 C2 Fe1 59.76(17) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
Fe1 C2 C3 C4 -58.92(16) . . . . ?
C1 C2 C3 Fe1 58.93(17) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
Fe1 C3 C4 C5 -59.39(17) . . . . ?
C2 C3 C4 Fe1 59.12(17) . . . . ?
C3 C4 C5 C1 0.4(3) . . . . ?
Fe1 C4 C5 C1 -59.32(17) . . . . ?
C3 C4 C5 Fe1 59.75(17) . . . . ?
C2 C1 C5 C4 -0.4(3) . . . . ?
Fe1 C1 C5 C4 59.55(17) . . . . ?
C2 C1 C5 Fe1 -59.97(17) . . . . ?
C10 C6 C7 C8 -1.7(3) . . . . ?
Fe1 C6 C7 C8 58.84(16) . . . . ?
C10 C6 C7 Fe1 -60.53(15) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
Fe1 C7 C8 C9 59.84(17) . . . . ?
C6 C7 C8 Fe1 -58.97(16) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
Fe1 C8 C9 C10 59.77(15) . . . . ?
C7 C8 C9 Fe1 -59.48(17) . . . . ?
C7 C6 C10 N11 -172.7(2) . . . . ?
Fe1 C6 C10 N11 127.2(2) . . . . ?
C7 C6 C10 C9 1.9(2) . . . . ?
Fe1 C6 C10 C9 -58.23(15) . . . . ?
C7 C6 C10 Fe1 60.10(15) . . . . ?
C8 C9 C10 N11 173.2(2) . . . . ?
Fe1 C9 C10 N11 -127.5(2) . . . . ?
C8 C9 C10 C6 -1.3(3) . . . . ?
Fe1 C9 C10 C6 57.94(15) . . . . ?
C8 C9 C10 Fe1 -59.28(16) . . . . ?
C6 C10 N11 C13 43.5(3) . . . . ?
C9 C10 N11 C13 -130.2(2) . . . . ?
Fe1 C10 N11 C13 136.0(2) . . . . ?
C6 C10 N11 C12 -137.0(2) . . . . ?
C9 C10 N11 C12 49.3(3) . . . . ?
Fe1 C10 N11 C12 -44.5(3) . . . . ?
C10 N11 C13 O14 -168.3(2) . . . . ?
C12 N11 C13 O14 12.2(3) . . . . ?
C10 N11 C13 C15 15.6(3) . . . . ?
C12 N11 C13 C15 -163.87(19) . . . . ?
O14 C13 C15 C20 -138.0(2) . . . . ?
N11 C13 C15 C20 38.2(3) . . . . ?
O14 C13 C15 C16 35.3(3) . . . . ?
N11 C13 C15 C16 -148.6(2) . . . . ?
C20 C15 C16 C17 -0.7(3) . . . . ?
C13 C15 C16 C17 -174.2(2) . . . . ?
C15 C16 C17 C18 1.6(4) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C17 C18 C19 Cl1 178.71(18) . . . . ?
C18 C19 C20 C15 1.6(3) . . . . ?
Cl1 C19 C20 C15 -177.88(16) . . . . ?
C16 C15 C20 C19 -0.8(3) . . . . ?
C13 C15 C20 C19 172.3(2) . . . . ?
C55 C51 C52 C53 0.0(3) . . . . ?
Fe2 C51 C52 C53 -59.60(17) . . . . ?
C55 C51 C52 Fe2 59.61(17) . . . . ?
C51 C52 C53 C54 -0.3(3) . . . . ?
Fe2 C52 C53 C54 -60.24(17) . . . . ?
C51 C52 C53 Fe2 59.91(17) . . . . ?
C52 C53 C54 C55 0.5(3) . . . . ?
Fe2 C53 C54 C55 -59.27(17) . . . . ?
C52 C53 C54 Fe2 59.80(17) . . . . ?
C53 C54 C55 C51 -0.5(3) . . . . ?
Fe2 C54 C55 C51 -59.18(17) . . . . ?
C53 C54 C55 Fe2 58.65(17) . . . . ?
C52 C51 C55 C54 0.3(3) . . . . ?
Fe2 C51 C55 C54 59.40(17) . . . . ?
C52 C51 C55 Fe2 -59.08(17) . . . . ?
C60 C56 C57 C58 0.6(3) . . . . ?
Fe2 C56 C57 C58 -59.17(17) . . . . ?
C60 C56 C57 Fe2 59.73(16) . . . . ?
C56 C57 C58 C59 0.6(3) . . . . ?
Fe2 C57 C58 C59 -59.25(16) . . . . ?
C56 C57 C58 Fe2 59.82(17) . . . . ?
C57 C58 C59 C60 -1.5(3) . . . . ?
Fe2 C58 C59 C60 -60.60(15) . . . . ?
C57 C58 C59 Fe2 59.14(17) . . . . ?
C57 C56 C60 N61 174.7(2) . . . . ?
Fe2 C56 C60 N61 -126.4(2) . . . . ?
C57 C56 C60 C59 -1.5(3) . . . . ?
Fe2 C56 C60 C59 57.51(16) . . . . ?
C57 C56 C60 Fe2 -58.98(16) . . . . ?
C58 C59 C60 N61 -174.3(2) . . . . ?
Fe2 C59 C60 N61 125.8(2) . . . . ?
C58 C59 C60 C56 1.8(3) . . . . ?
Fe2 C59 C60 C56 -58.06(16) . . . . ?
C58 C59 C60 Fe2 59.88(15) . . . . ?
C56 C60 N61 C63 -131.7(2) . . . . ?
C59 C60 N61 C63 43.8(3) . . . . ?
Fe2 C60 N61 C63 135.4(2) . . . . ?
C56 C60 N61 C62 47.0(3) . . . . ?
C59 C60 N61 C62 -137.5(2) . . . . ?
Fe2 C60 N61 C62 -45.9(3) . . . . ?
C60 N61 C63 O64 -168.9(2) . . . . ?
C62 N61 C63 O64 12.4(3) . . . . ?
C60 N61 C63 C65 14.6(3) . . . . ?
C62 N61 C63 C65 -164.11(19) . . . . ?
O64 C63 C65 C70 -138.7(2) . . . . ?
N61 C63 C65 C70 37.9(3) . . . . ?
O64 C63 C65 C66 33.7(3) . . . . ?
N61 C63 C65 C66 -149.7(2) . . . . ?
C70 C65 C66 C67 -1.3(3) . . . . ?
C63 C65 C66 C67 -174.0(2) . . . . ?
C65 C66 C67 C68 1.8(3) . . . . ?
C66 C67 C68 C69 -0.8(3) . . . . ?
C67 C68 C69 C70 -0.6(3) . . . . ?
C67 C68 C69 Cl2 -179.69(17) . . . . ?
C68 C69 C70 C65 1.1(3) . . . . ?
Cl2 C69 C70 C65 -179.85(16) . . . . ?
C66 C65 C70 C69 -0.1(3) . . . . ?
C63 C65 C70 C69 172.1(2) . . . . ?
