#------------------------------------------------------------------------------
#$Date: 2020-11-06 13:41:39 +0100 (vie 06 de nov de 2020) $
#$Revision: 258891 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/99/7059966.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_7059966
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         'C24 H20 Cl Fe N O'
_chemical_formula_sum            'C24 H20 Cl Fe N O'
_chemical_formula_weight         429.71
_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                99.381(2)
_cell_angle_beta                 91.4120(10)
_cell_angle_gamma                109.2600(10)
_cell_formula_units_Z            4
_cell_length_a                   10.9882(5)
_cell_length_b                   12.9018(5)
_cell_length_c                   14.8228(5)
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.4877
_cell_measurement_theta_min      2.4631
_cell_measurement_wavelength     0.710730
_cell_volume                     1950.30(14)
_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 0.985
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      -0.0943011
_diffrn_orient_matrix_UB_12      -0.0312436
_diffrn_orient_matrix_UB_13      0.0087025
_diffrn_orient_matrix_UB_21      0.0179052
_diffrn_orient_matrix_UB_22      -0.0519424
_diffrn_orient_matrix_UB_23      0.0375238
_diffrn_orient_matrix_UB_31      0.0124750
_diffrn_orient_matrix_UB_32      0.0573314
_diffrn_orient_matrix_UB_33      0.0568001
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29093
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         2.122
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_correction_T_min  0.647
_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    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         8850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0245P)²+1.8446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0788
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7363
_reflns_number_total             8850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0nj03470c2.cif
_cod_data_source_block           WE9701
_cod_depositor_comments
'Adding full bibliography for 7059953--7059970.cif.'
_cod_original_cell_volume        1950.30(13)
_cod_database_code               7059966
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
C1 C 0.30242(19) 0.25669(16) 0.50534(13) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.248936 0.297394 0.490726 0.027 Uiso 1 1 calc R U . . .
C2 C 0.29761(18) 0.15030(15) 0.45792(13) 0.0194(4) Uani 1 1 d . . . . .
H2 H 0.240108 0.107214 0.406150 0.023 Uiso 1 1 calc R U . . .
C3 C 0.39415(19) 0.11949(16) 0.50163(14) 0.0226(4) Uani 1 1 d . . . . .
H3 H 0.412413 0.052347 0.483990 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4583(2) 0.20686(17) 0.57626(13) 0.0260(4) Uani 1 1 d . . . . .
H4 H 0.526990 0.208410 0.617277 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4014(2) 0.29159(17) 0.57856(13) 0.0267(4) Uani 1 1 d . . . . .
H5 H 0.425412 0.359623 0.621535 0.032 Uiso 1 1 calc R U . . .
C6 C 0.50936(17) 0.38074(14) 0.37085(12) 0.0152(3) Uani 1 1 d . . . . .
H6 H 0.449082 0.414387 0.354442 0.018 Uiso 1 1 calc R U . . .
C7 C 0.60369(18) 0.42151(15) 0.44787(12) 0.0179(4) Uani 1 1 d . . . . .
H7 H 0.618412 0.488266 0.491162 0.021 Uiso 1 1 calc R U . . .
C8 C 0.67184(18) 0.34500(16) 0.44864(13) 0.0206(4) Uani 1 1 d . . . . .
H8 H 0.739047 0.351483 0.493018 0.025 Uiso 1 1 calc R U . . .
C9 C 0.62215(17) 0.25710(15) 0.37157(13) 0.0182(4) Uani 1 1 d . . . . .
H9 H 0.649988 0.194716 0.355286 0.022 Uiso 1 1 calc R U . . .
C10 C 0.52248(16) 0.28017(14) 0.32317(11) 0.0139(3) Uani 1 1 d . . . . .
N11 N 0.45223(14) 0.21491(12) 0.23959(10) 0.0154(3) Uani 1 1 d . . . . .
C12 C 0.40300(18) 0.09258(14) 0.23306(13) 0.0187(4) Uani 1 1 d . . . . .
H12A H 0.324125 0.060905 0.189969 0.022 Uiso 1 1 calc R U . . .
H12B H 0.378013 0.075330 0.294068 0.022 Uiso 1 1 calc R U . . .
C13 C 0.49919(17) 0.03624(14) 0.20108(12) 0.0172(4) Uani 1 1 d . . . . .
C14 C 0.55004(18) 0.04545(16) 0.11656(13) 0.0206(4) Uani 1 1 d . . . . .
H14 H 0.525796 0.089311 0.078653 0.025 Uiso 1 1 calc R U . . .
C15 C 0.63597(19) -0.00888(17) 0.08703(14) 0.0247(4) Uani 1 1 d . . . . .
H15 H 0.669840 -0.002180 0.029084 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6723(2) -0.07259(17) 0.14166(15) 0.0289(5) Uani 1 1 d . . . . .
H16 H 0.730794 -0.109907 0.121310 0.035 Uiso 1 1 calc R U . . .
C17 C 0.6231(2) -0.08181(19) 0.22598(16) 0.0344(5) Uani 1 1 d . . . . .
H17 H 0.648481 -0.125045 0.263945 0.041 Uiso 1 1 calc R U . . .
C18 C 0.5368(2) -0.02802(17) 0.25539(15) 0.0283(5) Uani 1 1 d . . . . .
H18 H 0.503027 -0.035206 0.313319 0.034 Uiso 1 1 calc R U . . .
C19 C 0.42300(17) 0.25819(15) 0.16689(12) 0.0173(4) Uani 1 1 d . . . . .
O20 O 0.34970(14) 0.19845(12) 0.10053(9) 0.0251(3) Uani 1 1 d . . . . .
C21 C 0.48336(18) 0.38155(15) 0.16785(12) 0.0172(4) Uani 1 1 d . . . . .
C22 C 0.61398(18) 0.44022(16) 0.19289(12) 0.0204(4) Uani 1 1 d . . . . .
H22 H 0.667855 0.403720 0.214848 0.024 Uiso 1 1 calc R U . . .
C23 C 0.6656(2) 0.55210(18) 0.18581(14) 0.0258(4) Uani 1 1 d . . . . .
H23 H 0.755144 0.591586 0.202077 0.031 Uiso 1 1 calc R U . . .
C24 C 0.5872(2) 0.60662(18) 0.15506(15) 0.0283(4) Uani 1 1 d . . . . .
H24 H 0.622048 0.683339 0.150707 0.034 Uiso 1 1 calc R U . . .
C25 C 0.4576(2) 0.54738(18) 0.13095(14) 0.0267(4) Uani 1 1 d . . . . .
C26 C 0.40420(19) 0.43540(17) 0.13541(13) 0.0226(4) Uani 1 1 d . . . . .
H26 H 0.315341 0.395713 0.116800 0.027 Uiso 1 1 calc R U . . .
C51 C 1.0519(2) 0.87876(17) 1.02289(14) 0.0261(4) Uani 1 1 d . . . . .
H51 H 1.087350 0.945596 0.999210 0.031 Uiso 1 1 calc R U . . .
C52 C 1.1203(2) 0.83342(19) 1.07911(14) 0.0318(5) Uani 1 1 d . . . . .
H52 H 1.209553 0.864910 1.099913 0.038 Uiso 1 1 calc R U . . .
C53 C 1.0323(3) 0.7331(2) 1.09866(14) 0.0347(5) Uani 1 1 d . . . . .
H53 H 1.051976 0.685530 1.134942 0.042 Uiso 1 1 calc R U . . .
C54 C 0.9095(2) 0.71624(19) 1.05452(14) 0.0319(5) Uani 1 1 d . . . . .
H54 H 0.832763 0.654919 1.055675 0.038 Uiso 1 1 calc R U . . .
C55 C 0.9210(2) 0.80655(18) 1.00839(13) 0.0254(4) Uani 1 1 d . . . . .
H55 H 0.853323 0.816937 0.973897 0.030 Uiso 1 1 calc R U . . .
C56 C 0.99420(19) 0.57271(15) 0.87278(12) 0.0184(4) Uani 1 1 d . . . . .
H56 H 0.917298 0.511154 0.872885 0.022 Uiso 1 1 calc R U . . .
C57 C 1.1138(2) 0.59472(16) 0.92410(13) 0.0229(4) Uani 1 1 d . . . . .
H57 H 1.131565 0.549325 0.963444 0.027 Uiso 1 1 calc R U . . .
C58 C 1.20225(19) 0.69663(17) 0.90627(13) 0.0223(4) Uani 1 1 d . . . . .
H58 H 1.288896 0.731543 0.932522 0.027 Uiso 1 1 calc R U . . .
C59 C 1.13863(18) 0.73754(15) 0.84218(12) 0.0188(4) Uani 1 1 d . . . . .
H59 H 1.174951 0.804053 0.818202 0.023 Uiso 1 1 calc R U . . .
C60 C 1.01051(17) 0.65980(14) 0.82104(11) 0.0147(3) Uani 1 1 d . . . . .
N61 N 0.91577(15) 0.66137(12) 0.75421(10) 0.0159(3) Uani 1 1 d . . . . .
C62 C 0.87470(19) 0.75938(15) 0.75894(13) 0.0188(4) Uani 1 1 d . . . . .
H62A H 0.870840 0.789599 0.824220 0.023 Uiso 1 1 calc R U . . .
H62B H 0.786095 0.735013 0.728544 0.023 Uiso 1 1 calc R U . . .
C63 C 0.96099(17) 0.85201(15) 0.71533(12) 0.0166(4) Uani 1 1 d . . . . .
C64 C 0.97536(19) 0.96158(16) 0.75359(13) 0.0224(4) Uani 1 1 d . . . . .
H64 H 0.937515 0.976436 0.809008 0.027 Uiso 1 1 calc R U . . .
C65 C 1.0441(2) 1.04951(18) 0.71204(16) 0.0318(5) Uani 1 1 d . . . . .
H65 H 1.052656 1.123981 0.738617 0.038 Uiso 1 1 calc R U . . .
C66 C 1.1004(2) 1.0283(2) 0.63160(17) 0.0372(5) Uani 1 1 d . . . . .
H66 H 1.146731 1.088225 0.602496 0.045 Uiso 1 1 calc R U . . .
C67 C 1.0890(2) 0.92007(19) 0.59379(15) 0.0332(5) Uani 1 1 d . . . . .
H67 H 1.129027 0.905668 0.539302 0.040 Uiso 1 1 calc R U . . .
C68 C 1.0192(2) 0.83222(17) 0.63529(14) 0.0252(4) Uani 1 1 d . . . . .
H68 H 1.011200 0.757888 0.608671 0.030 Uiso 1 1 calc R U . . .
C69 C 0.85623(18) 0.57063(16) 0.68785(13) 0.0205(4) Uani 1 1 d . . . . .
O70 O 0.76212(16) 0.56356(13) 0.63818(11) 0.0387(4) Uani 1 1 d . . . . .
C71 C 0.91395(18) 0.47904(15) 0.67275(12) 0.0172(4) Uani 1 1 d . . . . .
C72 C 1.03966(19) 0.49950(16) 0.64844(14) 0.0232(4) Uani 1 1 d . . . . .
H72 H 1.094407 0.573821 0.648106 0.028 Uiso 1 1 calc R U . . .
C73 C 1.0855(2) 0.41139(17) 0.62460(15) 0.0279(4) Uani 1 1 d . . . . .
H73 H 1.171405 0.425729 0.607362 0.033 Uiso 1 1 calc R U . . .
C74 C 1.0069(2) 0.30240(17) 0.62572(14) 0.0255(4) Uani 1 1 d . . . . .
H74 H 1.037935 0.241915 0.609154 0.031 Uiso 1 1 calc R U . . .
C75 C 0.88212(19) 0.28393(15) 0.65158(13) 0.0213(4) Uani 1 1 d . . . . .
C76 C 0.83352(18) 0.37015(15) 0.67405(13) 0.0193(4) Uani 1 1 d . . . . .
H76 H 0.747030 0.355491 0.690057 0.023 Uiso 1 1 calc R U . . .
Cl1 Cl 0.35872(6) 0.61654(5) 0.09346(5) 0.04885(18) Uani 1 1 d . . . . .
Cl2 Cl 0.78239(6) 0.14843(4) 0.65487(4) 0.03703(13) Uani 1 1 d . . . . .
Fe1 Fe 0.47794(2) 0.26730(2) 0.45591(2) 0.01416(6) Uani 1 1 d . . . . .
Fe2 Fe 1.04433(3) 0.72268(2) 0.96039(2) 0.01617(7) 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'
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
C5 C1 C2 107.97(18) . . ?
C5 C1 Fe1 69.39(11) . . ?
C2 C1 Fe1 70.23(11) . . ?
C5 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
Fe1 C1 H1 125.9 . . ?
C3 C2 C1 108.02(17) . . ?
C3 C2 Fe1 69.64(10) . . ?
C1 C2 Fe1 69.36(11) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 126.6 . . ?
C2 C3 C4 108.03(17) . . ?
C2 C3 Fe1 69.88(10) . . ?
C4 C3 Fe1 69.38(10) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
Fe1 C3 H3 126.3 . . ?
C5 C4 C3 107.83(18) . . ?
C5 C4 Fe1 69.41(11) . . ?
C3 C4 Fe1 70.10(11) . . ?
C5 C4 H4 126.1 . . ?
C3 C4 H4 126.1 . . ?
Fe1 C4 H4 126.0 . . ?
C1 C5 C4 108.14(18) . . ?
C1 C5 Fe1 69.94(11) . . ?
C4 C5 Fe1 69.86(11) . . ?
C1 C5 H5 125.9 . . ?
C4 C5 H5 125.9 . . ?
Fe1 C5 H5 125.8 . . ?
C10 C6 C7 107.29(16) . . ?
C10 C6 Fe1 70.52(10) . . ?
C7 C6 Fe1 69.59(10) . . ?
C10 C6 H6 126.4 . . ?
C7 C6 H6 126.4 . . ?
Fe1 C6 H6 125.1 . . ?
C8 C7 C6 108.31(16) . . ?
C8 C7 Fe1 69.98(10) . . ?
C6 C7 Fe1 69.35(10) . . ?
C8 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
Fe1 C7 H7 126.4 . . ?
C7 C8 C9 108.39(16) . . ?
C7 C8 Fe1 69.24(10) . . ?
C9 C8 Fe1 70.48(10) . . ?
C7 C8 H8 125.8 . . ?
C9 C8 H8 125.8 . . ?
Fe1 C8 H8 126.0 . . ?
C8 C9 C10 107.30(16) . . ?
C8 C9 Fe1 69.03(10) . . ?
C10 C9 Fe1 69.39(10) . . ?
C8 C9 H9 126.3 . . ?
C10 C9 H9 126.3 . . ?
Fe1 C9 H9 126.8 . . ?
N11 C10 C6 126.22(16) . . ?
N11 C10 C9 125.06(16) . . ?
C6 C10 C9 108.69(15) . . ?
N11 C10 Fe1 128.90(12) . . ?
C6 C10 Fe1 68.72(9) . . ?
C9 C10 Fe1 70.01(10) . . ?
C19 N11 C10 124.41(15) . . ?
C19 N11 C12 118.20(15) . . ?
C10 N11 C12 117.33(14) . . ?
N11 C12 C13 113.90(15) . . ?
N11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C18 C13 C14 118.50(17) . . ?
C18 C13 C12 120.29(17) . . ?
C14 C13 C12 121.21(17) . . ?
C15 C14 C13 120.64(18) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.22(18) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.70(19) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.79(19) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
O20 C19 N11 121.49(17) . . ?
O20 C19 C21 119.40(16) . . ?
N11 C19 C21 119.10(15) . . ?
C22 C21 C26 119.90(17) . . ?
C22 C21 C19 122.89(16) . . ?
C26 C21 C19 117.04(17) . . ?
C23 C22 C21 120.05(18) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.37(19) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 118.86(19) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C26 121.99(18) . . ?
C24 C25 Cl1 118.78(16) . . ?
C26 C25 Cl1 119.23(16) . . ?
C25 C26 C21 118.80(18) . . ?
C25 C26 H26 120.6 . . ?
C21 C26 H26 120.6 . . ?
C52 C51 C55 107.96(19) . . ?
C52 C51 Fe2 69.26(11) . . ?
C55 C51 Fe2 70.54(11) . . ?
C52 C51 H51 126.0 . . ?
C55 C51 H51 126.0 . . ?
Fe2 C51 H51 125.8 . . ?
C51 C52 C53 108.0(2) . . ?
C51 C52 Fe2 70.04(11) . . ?
C53 C52 Fe2 69.84(12) . . ?
C51 C52 H52 126.0 . . ?
C53 C52 H52 126.0 . . ?
Fe2 C52 H52 125.7 . . ?
C52 C53 C54 107.94(19) . . ?
C52 C53 Fe2 69.56(12) . . ?
C54 C53 Fe2 70.05(12) . . ?
C52 C53 H53 126.0 . . ?
C54 C53 H53 126.0 . . ?
Fe2 C53 H53 125.9 . . ?
C55 C54 C53 108.3(2) . . ?
C55 C54 Fe2 70.52(11) . . ?
C53 C54 Fe2 69.40(12) . . ?
C55 C54 H54 125.9 . . ?
C53 C54 H54 125.9 . . ?
Fe2 C54 H54 125.8 . . ?
C54 C55 C51 107.82(19) . . ?
C54 C55 Fe2 69.23(12) . . ?
C51 C55 Fe2 69.12(11) . . ?
C54 C55 H55 126.1 . . ?
C51 C55 H55 126.1 . . ?
Fe2 C55 H55 127.1 . . ?
C57 C56 C60 107.65(16) . . ?
C57 C56 Fe2 69.47(11) . . ?
C60 C56 Fe2 70.64(10) . . ?
C57 C56 H56 126.2 . . ?
C60 C56 H56 126.2 . . ?
Fe2 C56 H56 125.3 . . ?
C56 C57 C58 108.09(17) . . ?
C56 C57 Fe2 69.79(11) . . ?
C58 C57 Fe2 69.30(11) . . ?
C56 C57 H57 126.0 . . ?
C58 C57 H57 126.0 . . ?
Fe2 C57 H57 126.5 . . ?
C59 C58 C57 108.45(17) . . ?
C59 C58 Fe2 70.63(11) . . ?
C57 C58 Fe2 69.78(11) . . ?
C59 C58 H58 125.8 . . ?
C57 C58 H58 125.8 . . ?
Fe2 C58 H58 125.4 . . ?
C58 C59 C60 107.11(16) . . ?
C58 C59 Fe2 68.50(11) . . ?
C60 C59 Fe2 70.10(10) . . ?
C58 C59 H59 126.4 . . ?
C60 C59 H59 126.4 . . ?
Fe2 C59 H59 126.5 . . ?
C59 C60 N61 126.79(16) . . ?
C59 C60 C56 108.67(16) . . ?
N61 C60 C56 124.35(16) . . ?
C59 C60 Fe2 69.53(10) . . ?
N61 C60 Fe2 131.47(12) . . ?
C56 C60 Fe2 68.74(10) . . ?
C69 N61 C60 121.24(15) . . ?
C69 N61 C62 118.34(15) . . ?
C60 N61 C62 120.33(15) . . ?
N61 C62 C63 114.83(15) . . ?
N61 C62 H62A 108.6 . . ?
C63 C62 H62A 108.6 . . ?
N61 C62 H62B 108.6 . . ?
C63 C62 H62B 108.6 . . ?
H62A C62 H62B 107.5 . . ?
C68 C63 C64 118.64(18) . . ?
C68 C63 C62 122.88(17) . . ?
C64 C63 C62 118.33(16) . . ?
C65 C64 C63 120.95(19) . . ?
C65 C64 H64 119.5 . . ?
C63 C64 H64 119.5 . . ?
C66 C65 C64 119.7(2) . . ?
C66 C65 H65 120.1 . . ?
C64 C65 H65 120.1 . . ?
C67 C66 C65 119.9(2) . . ?
C67 C66 H66 120.0 . . ?
C65 C66 H66 120.0 . . ?
C66 C67 C68 120.1(2) . . ?
C66 C67 H67 119.9 . . ?
C68 C67 H67 119.9 . . ?
C63 C68 C67 120.63(19) . . ?
C63 C68 H68 119.7 . . ?
C67 C68 H68 119.7 . . ?
O70 C69 N61 122.55(17) . . ?
O70 C69 C71 119.49(17) . . ?
N61 C69 C71 117.88(16) . . ?
C72 C71 C76 120.22(17) . . ?
C72 C71 C69 121.22(17) . . ?
C76 C71 C69 118.21(17) . . ?
C71 C72 C73 119.99(18) . . ?
C71 C72 H72 120.0 . . ?
C73 C72 H72 120.0 . . ?
C74 C73 C72 120.60(19) . . ?
C74 C73 H73 119.7 . . ?
C72 C73 H73 119.7 . . ?
C73 C74 C75 118.47(18) . . ?
C73 C74 H74 120.8 . . ?
C75 C74 H74 120.8 . . ?
C74 C75 C76 121.96(18) . . ?
C74 C75 Cl2 119.38(15) . . ?
C76 C75 Cl2 118.65(15) . . ?
C75 C76 C71 118.73(18) . . ?
C75 C76 H76 120.6 . . ?
C71 C76 H76 120.6 . . ?
C6 Fe1 C7 41.06(7) . . ?
C6 Fe1 C5 121.38(8) . . ?
C7 Fe1 C5 103.81(8) . . ?
C6 Fe1 C8 68.97(7) . . ?
C7 Fe1 C8 40.78(8) . . ?
C5 Fe1 C8 118.63(8) . . ?
C6 Fe1 C1 105.46(7) . . ?
C7 Fe1 C1 118.09(8) . . ?
C5 Fe1 C1 40.68(8) . . ?
C8 Fe1 C1 153.49(8) . . ?
C6 Fe1 C4 158.52(8) . . ?
C7 Fe1 C4 122.12(8) . . ?
C5 Fe1 C4 40.73(9) . . ?
C8 Fe1 C4 106.80(8) . . ?
C1 Fe1 C4 68.43(8) . . ?
C6 Fe1 C10 40.76(7) . . ?
C7 Fe1 C10 68.26(7) . . ?
C5 Fe1 C10 160.00(8) . . ?
C8 Fe1 C10 68.11(7) . . ?
C1 Fe1 C10 125.42(8) . . ?
C4 Fe1 C10 158.97(8) . . ?
C6 Fe1 C3 158.22(8) . . ?
C7 Fe1 C3 160.57(8) . . ?
C5 Fe1 C3 68.22(8) . . ?
C8 Fe1 C3 126.11(8) . . ?
C1 Fe1 C3 68.16(8) . . ?
C4 Fe1 C3 40.51(8) . . ?
C10 Fe1 C3 124.91(7) . . ?
C6 Fe1 C2 121.34(7) . . ?
C7 Fe1 C2 154.81(8) . . ?
C5 Fe1 C2 68.14(8) . . ?
C8 Fe1 C2 164.11(8) . . ?
C1 Fe1 C2 40.41(7) . . ?
C4 Fe1 C2 68.18(8) . . ?
C10 Fe1 C2 110.81(7) . . ?
C3 Fe1 C2 40.48(8) . . ?
C6 Fe1 C9 68.93(7) . . ?
C7 Fe1 C9 68.46(7) . . ?
C5 Fe1 C9 155.43(8) . . ?
C8 Fe1 C9 40.49(7) . . ?
C1 Fe1 C9 163.64(8) . . ?
C4 Fe1 C9 122.37(8) . . ?
C10 Fe1 C9 40.59(7) . . ?
C3 Fe1 C9 111.04(8) . . ?
C2 Fe1 C9 128.36(7) . . ?
C58 Fe2 C52 103.15(9) . . ?
C58 Fe2 C57 40.92(8) . . ?
C52 Fe2 C57 118.69(8) . . ?
C58 Fe2 C56 68.79(8) . . ?
C52 Fe2 C56 156.11(8) . . ?
C57 Fe2 C56 40.74(8) . . ?
C58 Fe2 C53 118.34(9) . . ?
C52 Fe2 C53 40.60(10) . . ?
C57 Fe2 C53 104.02(8) . . ?
C56 Fe2 C53 121.99(9) . . ?
C58 Fe2 C51 120.98(9) . . ?
C52 Fe2 C51 40.71(8) . . ?
C57 Fe2 C51 155.82(9) . . ?
C56 Fe2 C51 162.46(8) . . ?
C53 Fe2 C51 68.27(9) . . ?
C58 Fe2 C54 155.76(9) . . ?
C52 Fe2 C54 68.17(10) . . ?
C57 Fe2 C54 121.85(9) . . ?
C56 Fe2 C54 109.54(9) . . ?
C53 Fe2 C54 40.55(9) . . ?
C51 Fe2 C54 68.00(9) . . ?
C58 Fe2 C59 40.87(7) . . ?
C52 Fe2 C59 120.63(9) . . ?
C57 Fe2 C59 68.73(8) . . ?
C56 Fe2 C59 68.74(7) . . ?
C53 Fe2 C59 155.27(9) . . ?
C51 Fe2 C59 108.20(8) . . ?
C54 Fe2 C59 162.90(9) . . ?
C58 Fe2 C55 159.26(9) . . ?
C52 Fe2 C55 68.06(8) . . ?
C57 Fe2 C55 159.82(9) . . ?
C56 Fe2 C55 126.60(8) . . ?
C53 Fe2 C55 67.97(9) . . ?
C51 Fe2 C55 40.35(8) . . ?
C54 Fe2 C55 40.25(9) . . ?
C59 Fe2 C55 126.19(8) . . ?
C58 Fe2 C60 68.08(7) . . ?
C52 Fe2 C60 158.84(9) . . ?
C57 Fe2 C60 68.07(7) . . ?
C56 Fe2 C60 40.61(7) . . ?
C53 Fe2 C60 160.55(9) . . ?
C51 Fe2 C60 126.07(8) . . ?
C54 Fe2 C60 127.40(8) . . ?
C59 Fe2 C60 40.37(7) . . ?
C55 Fe2 C60 113.09(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
C1 C5 1.423(3) . ?
C1 C2 1.420(3) . ?
C1 Fe1 2.0501(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.425(3) . ?
C2 Fe1 2.0616(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.422(3) . ?
C3 Fe1 2.0584(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.424(3) . ?
C4 Fe1 2.0489(18) . ?
C4 H4 0.9500 . ?
C5 Fe1 2.0429(19) . ?
C5 H5 0.9500 . ?
C6 C10 1.426(2) . ?
C6 C7 1.428(2) . ?
C6 Fe1 2.0349(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.424(3) . ?
C7 Fe1 2.0382(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.424(3) . ?
C8 Fe1 2.0479(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.431(2) . ?
C9 Fe1 2.0671(18) . ?
C9 H9 0.9500 . ?
C10 N11 1.423(2) . ?
C10 Fe1 2.0589(17) . ?
N11 C19 1.369(2) . ?
N11 C12 1.476(2) . ?
C12 C13 1.513(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.391(3) . ?
C13 C14 1.391(3) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 O20 1.231(2) . ?
C19 C21 1.506(3) . ?
C21 C22 1.392(3) . ?
C21 C26 1.399(3) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(3) . ?
C25 Cl1 1.748(2) . ?
C26 H26 0.9500 . ?
C51 C52 1.422(3) . ?
C51 C55 1.420(3) . ?
C51 Fe2 2.0490(19) . ?
C51 H51 0.9500 . ?
C52 C53 1.416(3) . ?
C52 Fe2 2.039(2) . ?
C52 H52 0.9500 . ?
C53 C54 1.418(3) . ?
C53 Fe2 2.042(2) . ?
C53 H53 0.9500 . ?
C54 C55 1.417(3) . ?
C54 Fe2 2.051(2) . ?
C54 H54 0.9500 . ?
C55 Fe2 2.0678(19) . ?
C55 H55 0.9500 . ?
C56 C57 1.421(3) . ?
C56 C60 1.427(2) . ?
C56 Fe2 2.0436(18) . ?
C56 H56 0.9500 . ?
C57 C58 1.423(3) . ?
C57 Fe2 2.0394(19) . ?
C57 H57 0.9500 . ?
C58 C59 1.430(3) . ?
C58 Fe2 2.0330(19) . ?
C58 H58 0.9500 . ?
C59 C60 1.425(3) . ?
C59 Fe2 2.0612(18) . ?
C59 H59 0.9500 . ?
C60 N61 1.427(2) . ?
C60 Fe2 2.0688(17) . ?
N61 C69 1.361(2) . ?
N61 C62 1.469(2) . ?
C62 C63 1.510(2) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C68 1.389(3) . ?
C63 C64 1.390(3) . ?
C64 C65 1.387(3) . ?
C64 H64 0.9500 . ?
C65 C66 1.386(3) . ?
C65 H65 0.9500 . ?
C66 C67 1.381(3) . ?
C66 H66 0.9500 . ?
C67 C68 1.389(3) . ?
C67 H67 0.9500 . ?
C68 H68 0.9500 . ?
C69 O70 1.224(2) . ?
C69 C71 1.505(3) . ?
C71 C72 1.387(3) . ?
C71 C76 1.395(3) . ?
C72 C73 1.388(3) . ?
C72 H72 0.9500 . ?
C73 C74 1.389(3) . ?
C73 H73 0.9500 . ?
C74 C75 1.387(3) . ?
C74 H74 0.9500 . ?
C75 C76 1.383(3) . ?
C75 Cl2 1.7395(19) . ?
C76 H76 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 -0.2(2) . . . . ?
Fe1 C1 C2 C3 59.11(13) . . . . ?
C5 C1 C2 Fe1 -59.34(13) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
Fe1 C2 C3 C4 59.10(13) . . . . ?
C1 C2 C3 Fe1 -58.93(12) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
Fe1 C3 C4 C5 59.38(13) . . . . ?
C2 C3 C4 Fe1 -59.41(13) . . . . ?
C2 C1 C5 C4 0.2(2) . . . . ?
Fe1 C1 C5 C4 -59.65(13) . . . . ?
C2 C1 C5 Fe1 59.87(13) . . . . ?
C3 C4 C5 C1 -0.1(2) . . . . ?
Fe1 C4 C5 C1 59.69(13) . . . . ?
C3 C4 C5 Fe1 -59.82(13) . . . . ?
C10 C6 C7 C8 -1.43(19) . . . . ?
Fe1 C6 C7 C8 59.33(12) . . . . ?
C10 C6 C7 Fe1 -60.76(11) . . . . ?
C6 C7 C8 C9 0.9(2) . . . . ?
Fe1 C7 C8 C9 59.84(13) . . . . ?
C6 C7 C8 Fe1 -58.94(12) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
Fe1 C8 C9 C10 59.06(12) . . . . ?
C7 C8 C9 Fe1 -59.07(12) . . . . ?
C7 C6 C10 N11 -176.46(16) . . . . ?
Fe1 C6 C10 N11 123.37(17) . . . . ?
C7 C6 C10 C9 1.43(19) . . . . ?
Fe1 C6 C10 C9 -58.74(12) . . . . ?
C7 C6 C10 Fe1 60.17(11) . . . . ?
C8 C9 C10 N11 177.04(16) . . . . ?
Fe1 C9 C10 N11 -124.14(17) . . . . ?
C8 C9 C10 C6 -0.88(19) . . . . ?
Fe1 C9 C10 C6 57.94(12) . . . . ?
C8 C9 C10 Fe1 -58.83(12) . . . . ?
C6 C10 N11 C19 40.3(3) . . . . ?
C9 C10 N11 C19 -137.22(18) . . . . ?
Fe1 C10 N11 C19 131.08(16) . . . . ?
C6 C10 N11 C12 -136.81(17) . . . . ?
C9 C10 N11 C12 45.6(2) . . . . ?
Fe1 C10 N11 C12 -46.1(2) . . . . ?
C19 N11 C12 C13 95.84(19) . . . . ?
C10 N11 C12 C13 -86.82(19) . . . . ?
N11 C12 C13 C18 122.09(19) . . . . ?
N11 C12 C13 C14 -59.1(2) . . . . ?
C18 C13 C14 C15 0.3(3) . . . . ?
C12 C13 C14 C15 -178.46(17) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C13 -0.4(4) . . . . ?
C14 C13 C18 C17 0.0(3) . . . . ?
C12 C13 C18 C17 178.8(2) . . . . ?
C10 N11 C19 O20 -171.65(17) . . . . ?
C12 N11 C19 O20 5.5(3) . . . . ?
C10 N11 C19 C21 9.1(3) . . . . ?
C12 N11 C19 C21 -173.77(15) . . . . ?
O20 C19 C21 C22 -134.11(19) . . . . ?
N11 C19 C21 C22 45.2(2) . . . . ?
O20 C19 C21 C26 41.1(2) . . . . ?
N11 C19 C21 C26 -139.58(17) . . . . ?
C26 C21 C22 C23 0.1(3) . . . . ?
C19 C21 C22 C23 175.21(17) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C23 C24 C25 Cl1 179.32(16) . . . . ?
C24 C25 C26 C21 1.8(3) . . . . ?
Cl1 C25 C26 C21 -178.29(15) . . . . ?
C22 C21 C26 C25 -1.5(3) . . . . ?
C19 C21 C26 C25 -176.85(17) . . . . ?
C55 C51 C52 C53 0.4(2) . . . . ?
Fe2 C51 C52 C53 -59.75(14) . . . . ?
C55 C51 C52 Fe2 60.18(13) . . . . ?
C51 C52 C53 C54 0.1(2) . . . . ?
Fe2 C52 C53 C54 -59.78(14) . . . . ?
C51 C52 C53 Fe2 59.87(14) . . . . ?
C52 C53 C54 C55 -0.6(2) . . . . ?
Fe2 C53 C54 C55 -60.06(14) . . . . ?
C52 C53 C54 Fe2 59.47(14) . . . . ?
C53 C54 C55 C51 0.9(2) . . . . ?
Fe2 C54 C55 C51 -58.51(13) . . . . ?
C53 C54 C55 Fe2 59.36(14) . . . . ?
C52 C51 C55 C54 -0.8(2) . . . . ?
Fe2 C51 C55 C54 58.58(13) . . . . ?
C52 C51 C55 Fe2 -59.37(13) . . . . ?
C60 C56 C57 C58 1.7(2) . . . . ?
Fe2 C56 C57 C58 -58.90(13) . . . . ?
C60 C56 C57 Fe2 60.62(12) . . . . ?
C56 C57 C58 C59 -1.1(2) . . . . ?
Fe2 C57 C58 C59 -60.30(13) . . . . ?
C56 C57 C58 Fe2 59.20(13) . . . . ?
C57 C58 C59 C60 0.0(2) . . . . ?
Fe2 C58 C59 C60 -59.74(12) . . . . ?
C57 C58 C59 Fe2 59.77(13) . . . . ?
C58 C59 C60 N61 -174.16(16) . . . . ?
Fe2 C59 C60 N61 127.12(17) . . . . ?
C58 C59 C60 C56 1.0(2) . . . . ?
Fe2 C59 C60 C56 -57.68(12) . . . . ?
C58 C59 C60 Fe2 58.72(12) . . . . ?
C57 C56 C60 C59 -1.7(2) . . . . ?
Fe2 C56 C60 C59 58.16(12) . . . . ?
C57 C56 C60 N61 173.62(16) . . . . ?
Fe2 C56 C60 N61 -126.50(16) . . . . ?
C57 C56 C60 Fe2 -59.88(12) . . . . ?
C59 C60 N61 C69 126.0(2) . . . . ?
C56 C60 N61 C69 -48.5(2) . . . . ?
Fe2 C60 N61 C69 -139.50(16) . . . . ?
C59 C60 N61 C62 -57.6(2) . . . . ?
C56 C60 N61 C62 127.90(18) . . . . ?
Fe2 C60 N61 C62 36.9(2) . . . . ?
C69 N61 C62 C63 -99.4(2) . . . . ?
C60 N61 C62 C63 84.1(2) . . . . ?
N61 C62 C63 C68 37.6(3) . . . . ?
N61 C62 C63 C64 -146.95(17) . . . . ?
C68 C63 C64 C65 1.3(3) . . . . ?
C62 C63 C64 C65 -174.37(19) . . . . ?
C63 C64 C65 C66 -0.5(3) . . . . ?
C64 C65 C66 C67 -0.7(4) . . . . ?
C65 C66 C67 C68 1.2(4) . . . . ?
C64 C63 C68 C67 -0.8(3) . . . . ?
C62 C63 C68 C67 174.66(19) . . . . ?
C66 C67 C68 C63 -0.5(3) . . . . ?
C60 N61 C69 O70 169.16(19) . . . . ?
C62 N61 C69 O70 -7.3(3) . . . . ?
C60 N61 C69 C71 -14.1(3) . . . . ?
C62 N61 C69 C71 169.46(16) . . . . ?
O70 C69 C71 C72 117.3(2) . . . . ?
N61 C69 C71 C72 -59.5(2) . . . . ?
O70 C69 C71 C76 -55.8(3) . . . . ?
N61 C69 C71 C76 127.33(19) . . . . ?
C76 C71 C72 C73 0.5(3) . . . . ?
C69 C71 C72 C73 -172.54(19) . . . . ?
C71 C72 C73 C74 -0.7(3) . . . . ?
C72 C73 C74 C75 -0.3(3) . . . . ?
C73 C74 C75 C76 1.5(3) . . . . ?
C73 C74 C75 Cl2 -179.24(16) . . . . ?
C74 C75 C76 C71 -1.6(3) . . . . ?
Cl2 C75 C76 C71 179.08(14) . . . . ?
C72 C71 C76 C75 0.6(3) . . . . ?
C69 C71 C76 C75 173.87(17) . . . . ?
