##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-10-31
_journal_date_accepted     2005-11-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      1
_journal_page_first     m12
_journal_page_last     m13
_journal_paper_category     EM
_journal_coeditor_code     RN6073
_publ_contact_author_name     'Prof. Wen-Yuan Gao'
_publ_contact_author_address
;
College of pharmaceuticals & biotechnology
Tianjin University
Tianjin, 300072
People's Republic of China
;
_publ_contact_author_email     cpzyyan@hotmail.com
_publ_contact_author_fax     '86-22-27891364'
_publ_contact_author_phone     '86-22-27891364'
_publ_section_title
;
1-[(2-Chlorophenyl)(4-chlorophenylimino)methyl]ferrocene
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yan Zhang' .
;
College of Pharmaceuticals & Biotechnology
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Wen-Yuan Gao' .
;
College of Pharmaceuticals & Biotechnology
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Hai-Xia Chen' .
;
College of Pharmaceuticals & Biotechnology
Tianjin University
Tianjin 300072
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-[(2-Chlorophenyl)(4-chlorophenylimino)methyl]ferrocene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H17 Cl2 Fe N'
_chemical_formula_sum     'C23 H17 Cl2 Fe N'
_chemical_formula_iupac     '[Fe (C5 H5) (C18 H12 Cl2 N)]'
_chemical_formula_weight     434.13
_chemical_melting_point     446
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.226(3)
_cell_length_b     17.288(6)
_cell_length_c     13.996(5)
_cell_angle_alpha     90.00
_cell_angle_beta     103.820(6)
_cell_angle_gamma     90.00
_cell_volume     1932.8(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2747
_cell_measurement_theta_min     2.79
_cell_measurement_theta_max     23.14
_cell_measurement_temperature     294(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     Red
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.492
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     888
_exptl_absorpt_coefficient_mu     1.064
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.720
_exptl_absorpt_correction_T_max     0.880
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10709
_diffrn_reflns_av_R_equivalents     0.0366
_diffrn_reflns_av_sigmaI/netI     0.0453
_diffrn_reflns_theta_min     1.91
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3918
_reflns_number_gt     2546
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0778
_refine_ls_R_factor_gt     0.0416
_refine_ls_wR_factor_gt     0.0939
_refine_ls_wR_factor_ref     0.1066
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     3918
_refine_ls_number_parameters     284
_refine_ls_number_restraints     8
_refine_ls_hydrogen_treatment     CONSTR
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0445P)²+0.4751P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.292
_refine_diff_density_min     -0.263
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'N' 'N' 0.0061 0.0033
                         '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'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Fe1 0.04210(5) 1.15546(2) 0.80381(3) 0.04694(15) Uani d . 1 . . Fe
    Cl1 0.20257(12) 0.61035(5) 0.96107(7) 0.0748(3) Uani d . 1 . . Cl
    N1 0.1753(4) 0.95056(15) 0.9168(2) 0.0706(8) Uani d . 1 A . N
    C1 -0.0892(4) 1.1548(2) 0.6610(3) 0.0729(11) Uani d . 1 . . C
    H1A -0.0447 1.1423 0.6039 0.087 Uiso calc R 1 . . H
    C2 -0.1608(4) 1.1020(2) 0.7159(3) 0.0703(10) Uani d . 1 . . C
    H2A -0.1733 1.0462 0.7040 0.084 Uiso calc R 1 . . H
    C3 -0.2093(4) 1.1428(2) 0.7915(3) 0.0711(10) Uani d . 1 . . C
    H3A -0.2625 1.1210 0.8411 0.085 Uiso calc R 1 . . H
    C4 -0.1676(4) 1.2211(2) 0.7821(3) 0.0674(9) Uani d . 1 . . C
    H4A -0.1866 1.2633 0.8249 0.081 Uiso calc R 1 . . H
    C5 -0.0951(4) 1.2289(2) 0.7023(3) 0.0705(10) Uani d . 1 . . C
    H5A -0.0553 1.2771 0.6791 0.085 Uiso calc R 1 . . H
    C6 0.2883(4) 1.13291(17) 0.8111(2) 0.0528(8) Uani d . 1 . . C
    H6A 0.3367 1.1215 0.7551 0.063 Uiso calc R 1 . . H
    C7 0.2689(4) 1.20758(18) 0.8491(3) 0.0620(9) Uani d . 1 . . C
    H7A 0.3025 1.2566 0.8244 0.074 Uiso calc R 1 . . H
    C8 0.1939(4) 1.19857(19) 0.9295(3) 0.0663(10) Uani d . 1 . . C
    H8A 0.1652 1.2407 0.9694 0.080 Uiso calc R 1 . . H
    C9 0.1627(4) 1.11882(18) 0.9411(2) 0.0580(8) Uani d . 1 . . C
    H9A 0.1101 1.0962 0.9905 0.070 Uiso calc R 1 . . H
    C10 0.2231(4) 1.07724(16) 0.8678(2) 0.0469(7) Uani d . 1 A . C
    C11 0.2273(3) 0.99278(16) 0.8571(2) 0.0466(7) Uani d D 1 . . C
    C12 0.1885(4) 0.86908(17) 0.9181(2) 0.0535(8) Uani d . 1 . . C
    C13 0.0524(4) 0.8229(2) 0.8733(3) 0.0650(9) Uani d . 1 A . C
    H13A -0.0433 0.8457 0.8346 0.078 Uiso calc R 1 . . H
    C14 0.0583(4) 0.74411(19) 0.8857(3) 0.0621(9) Uani d . 1 . . C
    H14A -0.0327 0.7138 0.8552 0.075 Uiso calc R 1 A . H
    C15 0.1983(4) 0.71032(16) 0.9430(2) 0.0495(7) Uani d . 1 A . C
    C16 0.3343(4) 0.75422(18) 0.9866(2) 0.0549(8) Uani d . 1 . . C
    H16A 0.4297 0.7308 1.0247 0.066 Uiso calc R 1 A . H
    C17 0.3288(4) 0.83326(18) 0.9737(2) 0.0573(8) Uani d . 1 A . C
    H17A 0.4216 0.8629 1.0031 0.069 Uiso calc R 1 . . H
    Cl2 0.5914(3) 0.96401(14) 0.86150(15) 0.0764(7) Uani d P 0.609(3) A 1 Cl
    C18 0.2665(5) 0.9622(2) 0.7640(2) 0.0442(14) Uani d PGD 0.609(3) A 1 C
    C19 0.1374(4) 0.9503(3) 0.6809(3) 0.062(2) Uani d PG 0.609(3) A 1 C
    H19A 0.0270 0.9587 0.6837 0.075 Uiso calc PR 0.609(3) A 1 H
    C20 0.1734(6) 0.9259(2) 0.5936(2) 0.0709(19) Uani d PG 0.609(3) A 1 C
    H20A 0.0871 0.9180 0.5380 0.085 Uiso calc PR 0.609(3) A 1 H
    C21 0.3385(7) 0.9133(2) 0.5894(3) 0.0645(16) Uani d PG 0.609(3) A 1 C
    H21A 0.3626 0.8970 0.5310 0.077 Uiso calc PR 0.609(3) A 1 H
    C22 0.4675(5) 0.9252(3) 0.6725(4) 0.062(2) Uani d PG 0.609(3) A 1 C
    H22A 0.5780 0.9168 0.6697 0.074 Uiso calc PR 0.609(3) A 1 H
    C23 0.4315(4) 0.9496(2) 0.7598(3) 0.0521(14) Uani d PG 0.609(3) A 1 C
    Cl2' 0.0965(4) 0.92729(19) 0.6488(2) 0.0791(12) Uani d P 0.391(3) A 2 Cl
    C18' 0.3528(6) 0.9637(4) 0.8018(4) 0.044(2) Uani d PGD 0.391(3) A 2 C
    C19' 0.5219(8) 0.9710(4) 0.8472(4) 0.049(3) Uani d PGU 0.391(3) A 2 C
    H19B 0.5547 0.9897 0.9112 0.059 Uiso calc PR 0.391(3) A 2 H
    C20' 0.6421(6) 0.9504(4) 0.7968(6) 0.067(3) Uani d PG 0.391(3) A 2 C
    H20B 0.7552 0.9553 0.8272 0.080 Uiso calc PR 0.391(3) A 2 H
    C21' 0.5931(9) 0.9225(4) 0.7011(6) 0.074(3) Uani d PG 0.391(3) A 2 C
    H21B 0.6735 0.9087 0.6675 0.089 Uiso calc PR 0.391(3) A 2 H
    C22' 0.4240(11) 0.9152(4) 0.6557(4) 0.062(4) Uani d PG 0.391(3) A 2 C
    H22B 0.3912 0.8965 0.5917 0.075 Uiso calc PR 0.391(3) A 2 H
    C23' 0.3039(7) 0.9358(4) 0.7061(4) 0.058(2) Uani d PG 0.391(3) A 2 C
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Fe1 C4 . 2.026(3) ?
    Fe1 C1 . 2.032(3) ?
    Fe1 C7 . 2.032(3) ?
    Fe1 C5 . 2.033(3) ?
    Fe1 C8 . 2.040(3) ?
    Fe1 C6 . 2.041(3) ?
    Fe1 C9 . 2.041(3) ?
    Fe1 C2 . 2.043(3) ?
    Fe1 C3 . 2.045(3) ?
    Fe1 C10 . 2.052(3) ?
    Cl1 C15 . 1.746(3) ?
    N1 C11 . 1.259(4) yes
    N1 C12 . 1.413(4) yes
    C1 C2 . 1.409(5) ?
    C1 C5 . 1.411(5) ?
    C1 H1A . 0.9800 ?
    C2 C3 . 1.406(5) ?
    C2 H2A . 0.9800 ?
    C3 C4 . 1.410(5) ?
    C3 H3A . 0.9800 ?
    C4 C5 . 1.392(5) ?
    C4 H4A . 0.9800 ?
    C5 H5A . 0.9800 ?
    C6 C7 . 1.419(4) ?
    C6 C10 . 1.431(4) yes
    C6 H6A . 0.9800 ?
    C7 C8 . 1.416(5) ?
    C7 H7A . 0.9800 ?
    C8 C9 . 1.419(4) ?
    C8 H8A . 0.9800 ?
    C9 C10 . 1.435(4) ?
    C9 H9A . 0.9800 ?
    C10 C11 . 1.469(4) yes
    C11 C18 . 1.510(4) yes
    C11 C18' . 1.517(5) ?
    C12 C17 . 1.376(4) ?
    C12 C13 . 1.396(4) ?
    C13 C14 . 1.372(4) ?
    C13 H13A . 0.9300 ?
    C14 C15 . 1.367(4) ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.369(4) ?
    C16 C17 . 1.378(4) ?
    C16 H16A . 0.9300 ?
    C17 H17A . 0.9300 ?
    Cl2 C23 . 1.710(4) ?
    C18 C19 . 1.3900 ?
    C18 C23 . 1.3900 ?
    C19 C20 . 1.3900 ?
    C19 H19A . 0.9300 ?
    C20 C21 . 1.3900 ?
    C20 H20A . 0.9300 ?
    C21 C22 . 1.3900 ?
    C21 H21A . 0.9300 ?
    C22 C23 . 1.3900 ?
    C22 H22A . 0.9300 ?
    Cl2' C23' . 1.709(6) ?
    C18' C19' . 1.3900 ?
    C18' C23' . 1.3900 ?
    C19' C20' . 1.3900 ?
    C19' H19B . 0.9300 ?
    C20' C21' . 1.3900 ?
    C20' H20B . 0.9300 ?
    C21' C22' . 1.3900 ?
    C21' H21B . 0.9300 ?
    C22' C23' . 1.3900 ?
    C22' H22B . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C4 Fe1 C1 . . 67.80(15) ?
    C4 Fe1 C7 . . 118.93(14) ?
    C1 Fe1 C7 . . 122.82(16) ?
    C4 Fe1 C5 . . 40.10(14) ?
    C1 Fe1 C5 . . 40.62(14) ?
    C7 Fe1 C5 . . 104.84(15) ?
    C4 Fe1 C8 . . 104.39(14) ?
    C1 Fe1 C8 . . 157.30(16) ?
    C7 Fe1 C8 . . 40.70(13) ?
    C5 Fe1 C8 . . 119.84(15) ?
    C4 Fe1 C6 . . 156.00(14) ?
    C1 Fe1 C6 . . 109.64(14) ?
    C7 Fe1 C6 . . 40.78(12) ?
    C5 Fe1 C6 . . 122.19(15) ?
    C8 Fe1 C6 . . 68.34(14) ?
    C4 Fe1 C9 . . 121.33(14) ?
    C1 Fe1 C9 . . 161.54(15) ?
    C7 Fe1 C9 . . 68.94(14) ?
    C5 Fe1 C9 . . 156.19(14) ?
    C8 Fe1 C9 . . 40.69(13) ?
    C6 Fe1 C9 . . 68.92(13) ?
    C4 Fe1 C2 . . 67.62(15) ?
    C1 Fe1 C2 . . 40.47(14) ?
    C7 Fe1 C2 . . 161.04(16) ?
    C5 Fe1 C2 . . 67.95(15) ?
    C8 Fe1 C2 . . 158.20(17) ?
    C6 Fe1 C2 . . 127.02(14) ?
    C9 Fe1 C2 . . 124.73(15) ?
    C4 Fe1 C3 . . 40.53(13) ?
    C1 Fe1 C3 . . 68.13(15) ?
    C7 Fe1 C3 . . 155.25(15) ?
    C5 Fe1 C3 . . 68.08(15) ?
    C8 Fe1 C3 . . 120.65(16) ?
    C6 Fe1 C3 . . 162.75(14) ?
    C9 Fe1 C3 . . 107.46(15) ?
    C2 Fe1 C3 . . 40.24(14) ?
    C4 Fe1 C10 . . 159.66(14) ?
    C1 Fe1 C10 . . 125.81(14) ?
    C7 Fe1 C10 . . 68.88(12) ?
    C5 Fe1 C10 . . 160.02(15) ?
    C8 Fe1 C10 . . 68.50(12) ?
    C6 Fe1 C10 . . 40.92(12) ?
    C9 Fe1 C10 . . 41.06(11) ?
    C2 Fe1 C10 . . 111.58(13) ?
    C3 Fe1 C10 . . 125.44(13) ?
    C11 N1 C12 . . 123.3(3) yes
    C2 C1 C5 . . 107.7(3) ?
    C2 C1 Fe1 . . 70.2(2) ?
    C5 C1 Fe1 . . 69.74(19) ?
    C2 C1 H1A . . 126.1 ?
    C5 C1 H1A . . 126.1 ?
    Fe1 C1 H1A . . 126.1 ?
    C3 C2 C1 . . 108.4(3) ?
    C3 C2 Fe1 . . 70.0(2) ?
    C1 C2 Fe1 . . 69.35(19) ?
    C3 C2 H2A . . 125.8 ?
    C1 C2 H2A . . 125.8 ?
    Fe1 C2 H2A . . 125.8 ?
    C2 C3 C4 . . 107.0(3) ?
    C2 C3 Fe1 . . 69.78(19) ?
    C4 C3 Fe1 . . 69.02(19) ?
    C2 C3 H3A . . 126.5 ?
    C4 C3 H3A . . 126.5 ?
    Fe1 C3 H3A . . 126.5 ?
    C5 C4 C3 . . 109.1(3) ?
    C5 C4 Fe1 . . 70.22(19) ?
    C3 C4 Fe1 . . 70.45(19) ?
    C5 C4 H4A . . 125.4 ?
    C3 C4 H4A . . 125.4 ?
    Fe1 C4 H4A . . 125.4 ?
    C4 C5 C1 . . 107.7(3) ?
    C4 C5 Fe1 . . 69.69(19) ?
    C1 C5 Fe1 . . 69.64(19) ?
    C4 C5 H5A . . 126.1 ?
    C1 C5 H5A . . 126.1 ?
    Fe1 C5 H5A . . 126.1 ?
    C7 C6 C10 . . 108.3(3) ?
    C7 C6 Fe1 . . 69.28(17) ?
    C10 C6 Fe1 . . 69.95(17) ?
    C7 C6 H6A . . 125.9 ?
    C10 C6 H6A . . 125.9 ?
    Fe1 C6 H6A . . 125.9 ?
    C8 C7 C6 . . 107.9(3) ?
    C8 C7 Fe1 . . 69.94(19) ?
    C6 C7 Fe1 . . 69.94(17) ?
    C8 C7 H7A . . 126.1 ?
    C6 C7 H7A . . 126.1 ?
    Fe1 C7 H7A . . 126.1 ?
    C7 C8 C9 . . 108.8(3) ?
    C7 C8 Fe1 . . 69.37(18) ?
    C9 C8 Fe1 . . 69.70(17) ?
    C7 C8 H8A . . 125.6 ?
    C9 C8 H8A . . 125.6 ?
    Fe1 C8 H8A . . 125.6 ?
    C8 C9 C10 . . 107.6(3) ?
    C8 C9 Fe1 . . 69.61(18) ?
    C10 C9 Fe1 . . 69.87(17) ?
    C8 C9 H9A . . 126.2 ?
    C10 C9 H9A . . 126.2 ?
    Fe1 C9 H9A . . 126.2 ?
    C6 C10 C9 . . 107.4(3) ?
    C6 C10 C11 . . 126.2(3) ?
    C9 C10 C11 . . 126.3(3) ?
    C6 C10 Fe1 . . 69.14(16) ?
    C9 C10 Fe1 . . 69.07(16) ?
    C11 C10 Fe1 . . 130.0(2) ?
    N1 C11 C10 . . 119.2(3) yes
    N1 C11 C18 . . 123.1(3) yes
    C10 C11 C18 . . 116.8(3) ?
    N1 C11 C18' . . 121.8(3) ?
    C10 C11 C18' . . 114.6(3) ?
    C18 C11 C18' . . 29.8(2) ?
    C17 C12 C13 . . 118.1(3) ?
    C17 C12 N1 . . 120.5(3) yes
    C13 C12 N1 . . 120.9(3) ?
    C14 C13 C12 . . 120.7(3) ?
    C14 C13 H13A . . 119.6 ?
    C12 C13 H13A . . 119.6 ?
    C15 C14 C13 . . 119.8(3) ?
    C15 C14 H14A . . 120.1 ?
    C13 C14 H14A . . 120.1 ?
    C14 C15 C16 . . 120.6(3) ?
    C14 C15 Cl1 . . 119.5(2) ?
    C16 C15 Cl1 . . 119.9(2) ?
    C15 C16 C17 . . 119.6(3) ?
    C15 C16 H16A . . 120.2 ?
    C17 C16 H16A . . 120.2 ?
    C12 C17 C16 . . 121.1(3) ?
    C12 C17 H17A . . 119.4 ?
    C16 C17 H17A . . 119.4 ?
    C19 C18 C23 . . 120.0 ?
    C19 C18 C11 . . 119.7(3) ?
    C23 C18 C11 . . 120.2(3) ?
    C20 C19 C18 . . 120.0 ?
    C20 C19 H19A . . 120.0 ?
    C18 C19 H19A . . 120.0 ?
    C19 C20 C21 . . 120.0 ?
    C19 C20 H20A . . 120.0 ?
    C21 C20 H20A . . 120.0 ?
    C22 C21 C20 . . 120.0 ?
    C22 C21 H21A . . 120.0 ?
    C20 C21 H21A . . 120.0 ?
    C21 C22 C23 . . 120.0 ?
    C21 C22 H22A . . 120.0 ?
    C23 C22 H22A . . 120.0 ?
    C22 C23 C18 . . 120.0 ?
    C22 C23 Cl2 . . 119.5(3) ?
    C18 C23 Cl2 . . 120.5(3) ?
    C19' C18' C23' . . 120.0 ?
    C19' C18' C11 . . 117.8(5) ?
    C23' C18' C11 . . 122.1(5) ?
    C18' C19' C20' . . 120.0 ?
    C18' C19' H19B . . 120.0 ?
    C20' C19' H19B . . 120.0 ?
    C21' C20' C19' . . 120.0 ?
    C21' C20' H20B . . 120.0 ?
    C19' C20' H20B . . 120.0 ?
    C20' C21' C22' . . 120.0 ?
    C20' C21' H21B . . 120.0 ?
    C22' C21' H21B . . 120.0 ?
    C23' C22' C21' . . 120.0 ?
    C23' C22' H22B . . 120.0 ?
    C21' C22' H22B . . 120.0 ?
    C22' C23' C18' . . 120.0 ?
    C22' C23' Cl2' . . 119.4(5) ?
    C18' C23' Cl2' . . 120.6(5) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C4 Fe1 C1 C2 . . . . -81.1(2) ?
    C7 Fe1 C1 C2 . . . . 167.9(2) ?
    C5 Fe1 C1 C2 . . . . -118.6(3) ?
    C8 Fe1 C1 C2 . . . . -154.8(3) ?
    C6 Fe1 C1 C2 . . . . 124.5(2) ?
    C9 Fe1 C1 C2 . . . . 42.4(5) ?
    C3 Fe1 C1 C2 . . . . -37.2(2) ?
    C10 Fe1 C1 C2 . . . . 81.6(3) ?
    C4 Fe1 C1 C5 . . . . 37.5(2) ?
    C7 Fe1 C1 C5 . . . . -73.5(3) ?
    C8 Fe1 C1 C5 . . . . -36.3(5) ?
    C6 Fe1 C1 C5 . . . . -116.9(2) ?
    C9 Fe1 C1 C5 . . . . 160.9(4) ?
    C2 Fe1 C1 C5 . . . . 118.6(3) ?
    C3 Fe1 C1 C5 . . . . 81.4(2) ?
    C10 Fe1 C1 C5 . . . . -159.9(2) ?
    C5 C1 C2 C3 . . . . -0.6(4) ?
    Fe1 C1 C2 C3 . . . . 59.3(2) ?
    C5 C1 C2 Fe1 . . . . -59.9(2) ?
    C4 Fe1 C2 C3 . . . . -38.2(2) ?
    C1 Fe1 C2 C3 . . . . -119.8(3) ?
    C7 Fe1 C2 C3 . . . . -152.5(4) ?
    C5 Fe1 C2 C3 . . . . -81.7(2) ?
    C8 Fe1 C2 C3 . . . . 34.0(5) ?
    C6 Fe1 C2 C3 . . . . 163.8(2) ?
    C9 Fe1 C2 C3 . . . . 75.3(3) ?
    C10 Fe1 C2 C3 . . . . 119.9(2) ?
    C4 Fe1 C2 C1 . . . . 81.6(2) ?
    C7 Fe1 C2 C1 . . . . -32.7(5) ?
    C5 Fe1 C2 C1 . . . . 38.1(2) ?
    C8 Fe1 C2 C1 . . . . 153.8(3) ?
    C6 Fe1 C2 C1 . . . . -76.4(3) ?
    C9 Fe1 C2 C1 . . . . -164.9(2) ?
    C3 Fe1 C2 C1 . . . . 119.8(3) ?
    C10 Fe1 C2 C1 . . . . -120.4(2) ?
    C1 C2 C3 C4 . . . . 0.3(4) ?
    Fe1 C2 C3 C4 . . . . 59.2(2) ?
    C1 C2 C3 Fe1 . . . . -58.9(2) ?
    C4 Fe1 C3 C2 . . . . 118.4(3) ?
    C1 Fe1 C3 C2 . . . . 37.4(2) ?
    C7 Fe1 C3 C2 . . . . 159.0(3) ?
    C5 Fe1 C3 C2 . . . . 81.3(2) ?
    C8 Fe1 C3 C2 . . . . -166.0(2) ?
    C6 Fe1 C3 C2 . . . . -48.5(6) ?
    C9 Fe1 C3 C2 . . . . -123.6(2) ?
    C10 Fe1 C3 C2 . . . . -81.8(3) ?
    C1 Fe1 C3 C4 . . . . -81.0(2) ?
    C7 Fe1 C3 C4 . . . . 40.6(5) ?
    C5 Fe1 C3 C4 . . . . -37.0(2) ?
    C8 Fe1 C3 C4 . . . . 75.6(3) ?
    C6 Fe1 C3 C4 . . . . -166.9(4) ?
    C9 Fe1 C3 C4 . . . . 118.1(2) ?
    C2 Fe1 C3 C4 . . . . -118.4(3) ?
    C10 Fe1 C3 C4 . . . . 159.8(2) ?
    C2 C3 C4 C5 . . . . 0.1(4) ?
    Fe1 C3 C4 C5 . . . . 59.8(2) ?
    C2 C3 C4 Fe1 . . . . -59.7(2) ?
    C1 Fe1 C4 C5 . . . . -38.0(2) ?
    C7 Fe1 C4 C5 . . . . 78.3(3) ?
    C8 Fe1 C4 C5 . . . . 119.5(2) ?
    C6 Fe1 C4 C5 . . . . 50.6(4) ?
    C9 Fe1 C4 C5 . . . . 160.0(2) ?
    C2 Fe1 C4 C5 . . . . -81.9(2) ?
    C3 Fe1 C4 C5 . . . . -119.8(3) ?
    C10 Fe1 C4 C5 . . . . -173.8(3) ?
    C1 Fe1 C4 C3 . . . . 81.8(2) ?
    C7 Fe1 C4 C3 . . . . -161.8(2) ?
    C5 Fe1 C4 C3 . . . . 119.8(3) ?
    C8 Fe1 C4 C3 . . . . -120.7(2) ?
    C6 Fe1 C4 C3 . . . . 170.5(3) ?
    C9 Fe1 C4 C3 . . . . -80.1(3) ?
    C2 Fe1 C4 C3 . . . . 37.9(2) ?
    C10 Fe1 C4 C3 . . . . -54.0(5) ?
    C3 C4 C5 C1 . . . . -0.5(4) ?
    Fe1 C4 C5 C1 . . . . 59.5(2) ?
    C3 C4 C5 Fe1 . . . . -59.9(2) ?
    C2 C1 C5 C4 . . . . 0.7(4) ?
    Fe1 C1 C5 C4 . . . . -59.5(2) ?
    C2 C1 C5 Fe1 . . . . 60.2(2) ?
    C1 Fe1 C5 C4 . . . . 118.9(3) ?
    C7 Fe1 C5 C4 . . . . -117.5(2) ?
    C8 Fe1 C5 C4 . . . . -76.3(3) ?
    C6 Fe1 C5 C4 . . . . -158.2(2) ?
    C9 Fe1 C5 C4 . . . . -46.2(5) ?
    C2 Fe1 C5 C4 . . . . 81.0(2) ?
    C3 Fe1 C5 C4 . . . . 37.4(2) ?
    C10 Fe1 C5 C4 . . . . 173.7(3) ?
    C4 Fe1 C5 C1 . . . . -118.9(3) ?
    C7 Fe1 C5 C1 . . . . 123.5(2) ?
    C8 Fe1 C5 C1 . . . . 164.7(2) ?
    C6 Fe1 C5 C1 . . . . 82.9(2) ?
    C9 Fe1 C5 C1 . . . . -165.2(3) ?
    C2 Fe1 C5 C1 . . . . -38.0(2) ?
    C3 Fe1 C5 C1 . . . . -81.5(2) ?
    C10 Fe1 C5 C1 . . . . 54.8(5) ?
    C4 Fe1 C6 C7 . . . . 38.5(4) ?
    C1 Fe1 C6 C7 . . . . 117.9(2) ?
    C5 Fe1 C6 C7 . . . . 74.6(2) ?
    C8 Fe1 C6 C7 . . . . -37.9(2) ?
    C9 Fe1 C6 C7 . . . . -81.8(2) ?
    C2 Fe1 C6 C7 . . . . 159.9(2) ?
    C3 Fe1 C6 C7 . . . . -162.8(5) ?
    C10 Fe1 C6 C7 . . . . -119.7(3) ?
    C4 Fe1 C6 C10 . . . . 158.2(3) ?
    C1 Fe1 C6 C10 . . . . -122.5(2) ?
    C7 Fe1 C6 C10 . . . . 119.7(3) ?
    C5 Fe1 C6 C10 . . . . -165.77(19) ?
    C8 Fe1 C6 C10 . . . . 81.73(19) ?
    C9 Fe1 C6 C10 . . . . 37.89(17) ?
    C2 Fe1 C6 C10 . . . . -80.4(2) ?
    C3 Fe1 C6 C10 . . . . -43.1(5) ?
    C10 C6 C7 C8 . . . . 0.6(3) ?
    Fe1 C6 C7 C8 . . . . 59.9(2) ?
    C10 C6 C7 Fe1 . . . . -59.3(2) ?
    C4 Fe1 C7 C8 . . . . 78.0(2) ?
    C1 Fe1 C7 C8 . . . . 159.0(2) ?
    C5 Fe1 C7 C8 . . . . 118.8(2) ?
    C6 Fe1 C7 C8 . . . . -118.8(3) ?
    C9 Fe1 C7 C8 . . . . -37.02(18) ?
    C2 Fe1 C7 C8 . . . . -176.3(4) ?
    C3 Fe1 C7 C8 . . . . 49.1(4) ?
    C10 Fe1 C7 C8 . . . . -81.2(2) ?
    C4 Fe1 C7 C6 . . . . -163.2(2) ?
    C1 Fe1 C7 C6 . . . . -82.2(2) ?
    C5 Fe1 C7 C6 . . . . -122.4(2) ?
    C8 Fe1 C7 C6 . . . . 118.8(3) ?
    C9 Fe1 C7 C6 . . . . 81.7(2) ?
    C2 Fe1 C7 C6 . . . . -57.5(5) ?
    C3 Fe1 C7 C6 . . . . 167.9(3) ?
    C10 Fe1 C7 C6 . . . . 37.59(19) ?
    C6 C7 C8 C9 . . . . -1.2(4) ?
    Fe1 C7 C8 C9 . . . . 58.7(2) ?
    C6 C7 C8 Fe1 . . . . -59.9(2) ?
    C4 Fe1 C8 C7 . . . . -117.9(2) ?
    C1 Fe1 C8 C7 . . . . -51.3(4) ?
    C5 Fe1 C8 C7 . . . . -77.6(2) ?
    C6 Fe1 C8 C7 . . . . 38.03(18) ?
    C9 Fe1 C8 C7 . . . . 120.5(3) ?
    C2 Fe1 C8 C7 . . . . 176.8(3) ?
    C3 Fe1 C8 C7 . . . . -158.40(19) ?
    C10 Fe1 C8 C7 . . . . 82.2(2) ?
    C4 Fe1 C8 C9 . . . . 121.7(2) ?
    C1 Fe1 C8 C9 . . . . -171.7(3) ?
    C7 Fe1 C8 C9 . . . . -120.5(3) ?
    C5 Fe1 C8 C9 . . . . 161.9(2) ?
    C6 Fe1 C8 C9 . . . . -82.4(2) ?
    C2 Fe1 C8 C9 . . . . 56.3(4) ?
    C3 Fe1 C8 C9 . . . . 81.1(2) ?
    C10 Fe1 C8 C9 . . . . -38.28(19) ?
    C7 C8 C9 C10 . . . . 1.4(4) ?
    Fe1 C8 C9 C10 . . . . 59.8(2) ?
    C7 C8 C9 Fe1 . . . . -58.5(2) ?
    C4 Fe1 C9 C8 . . . . -74.8(2) ?
    C1 Fe1 C9 C8 . . . . 169.9(4) ?
    C7 Fe1 C9 C8 . . . . 37.0(2) ?
    C5 Fe1 C9 C8 . . . . -41.8(4) ?
    C6 Fe1 C9 C8 . . . . 80.9(2) ?
    C2 Fe1 C9 C8 . . . . -157.9(2) ?
    C3 Fe1 C9 C8 . . . . -117.0(2) ?
    C10 Fe1 C9 C8 . . . . 118.6(3) ?
    C4 Fe1 C9 C10 . . . . 166.51(19) ?
    C1 Fe1 C9 C10 . . . . 51.3(5) ?
    C7 Fe1 C9 C10 . . . . -81.6(2) ?
    C5 Fe1 C9 C10 . . . . -160.5(3) ?
    C8 Fe1 C9 C10 . . . . -118.6(3) ?
    C6 Fe1 C9 C10 . . . . -37.77(18) ?
    C2 Fe1 C9 C10 . . . . 83.4(2) ?
    C3 Fe1 C9 C10 . . . . 124.4(2) ?
    C7 C6 C10 C9 . . . . 0.2(3) ?
    Fe1 C6 C10 C9 . . . . -58.7(2) ?
    C7 C6 C10 C11 . . . . -176.2(3) ?
    Fe1 C6 C10 C11 . . . . 125.0(3) ?
    C7 C6 C10 Fe1 . . . . 58.8(2) ?
    C8 C9 C10 C6 . . . . -0.9(3) ?
    Fe1 C9 C10 C6 . . . . 58.7(2) ?
    C8 C9 C10 C11 . . . . 175.4(3) ?
    Fe1 C9 C10 C11 . . . . -125.0(3) ?
    C8 C9 C10 Fe1 . . . . -59.6(2) ?
    C4 Fe1 C10 C6 . . . . -154.2(4) ?
    C1 Fe1 C10 C6 . . . . 78.5(2) ?
    C7 Fe1 C10 C6 . . . . -37.47(19) ?
    C5 Fe1 C10 C6 . . . . 37.5(5) ?
    C8 Fe1 C10 C6 . . . . -81.3(2) ?
    C9 Fe1 C10 C6 . . . . -119.2(3) ?
    C2 Fe1 C10 C6 . . . . 122.2(2) ?
    C3 Fe1 C10 C6 . . . . 165.6(2) ?
    C4 Fe1 C10 C9 . . . . -35.0(5) ?
    C1 Fe1 C10 C9 . . . . -162.3(2) ?
    C7 Fe1 C10 C9 . . . . 81.8(2) ?
    C5 Fe1 C10 C9 . . . . 156.8(4) ?
    C8 Fe1 C10 C9 . . . . 37.9(2) ?
    C6 Fe1 C10 C9 . . . . 119.2(3) ?
    C2 Fe1 C10 C9 . . . . -118.6(2) ?
    C3 Fe1 C10 C9 . . . . -75.2(2) ?
    C4 Fe1 C10 C11 . . . . 85.4(5) ?
    C1 Fe1 C10 C11 . . . . -41.9(3) ?
    C7 Fe1 C10 C11 . . . . -157.9(3) ?
    C5 Fe1 C10 C11 . . . . -82.9(5) ?
    C8 Fe1 C10 C11 . . . . 158.3(3) ?
    C6 Fe1 C10 C11 . . . . -120.4(3) ?
    C9 Fe1 C10 C11 . . . . 120.4(4) ?
    C2 Fe1 C10 C11 . . . . 1.8(3) ?
    C3 Fe1 C10 C11 . . . . 45.2(3) ?
    C12 N1 C11 C10 . . . . -174.0(3) yes
    C12 N1 C11 C18 . . . . 16.9(5) yes
    C12 N1 C11 C18' . . . . -18.5(6) ?
    C6 C10 C11 N1 . . . . 175.1(3) yes
    C9 C10 C11 N1 . . . . -0.6(5) ?
    Fe1 C10 C11 N1 . . . . -92.7(3) ?
    C6 C10 C11 C18 . . . . -15.2(4) ?
    C9 C10 C11 C18 . . . . 169.2(3) ?
    Fe1 C10 C11 C18 . . . . 77.0(4) ?
    C6 C10 C11 C18' . . . . 17.9(5) ?
    C9 C10 C11 C18' . . . . -157.8(4) ?
    Fe1 C10 C11 C18' . . . . 110.1(4) ?
    C11 N1 C12 C17 . . . . 88.9(4) ?
    C11 N1 C12 C13 . . . . -99.2(4) yes
    C17 C12 C13 C14 . . . . 0.8(5) ?
    N1 C12 C13 C14 . . . . -171.3(3) ?
    C12 C13 C14 C15 . . . . 0.4(5) ?
    C13 C14 C15 C16 . . . . -1.3(5) ?
    C13 C14 C15 Cl1 . . . . 178.2(3) ?
    C14 C15 C16 C17 . . . . 0.9(5) ?
    Cl1 C15 C16 C17 . . . . -178.6(2) ?
    C13 C12 C17 C16 . . . . -1.2(5) ?
    N1 C12 C17 C16 . . . . 170.9(3) ?
    C15 C16 C17 C12 . . . . 0.4(5) ?
    N1 C11 C18 C19 . . . . 81.1(4) yes
    C10 C11 C18 C19 . . . . -88.3(3) ?
    C18' C11 C18 C19 . . . . 178.5(8) ?
    N1 C11 C18 C23 . . . . -102.2(4) ?
    C10 C11 C18 C23 . . . . 88.5(4) ?
    C18' C11 C18 C23 . . . . -4.8(6) ?
    C23 C18 C19 C20 . . . . 0.0 ?
    C11 C18 C19 C20 . . . . 176.7(4) ?
    C18 C19 C20 C21 . . . . 0.0 ?
    C19 C20 C21 C22 . . . . 0.0 ?
    C20 C21 C22 C23 . . . . 0.0 ?
    C21 C22 C23 C18 . . . . 0.0 ?
    C21 C22 C23 Cl2 . . . . -180.0(3) ?
    C19 C18 C23 C22 . . . . 0.0 ?
    C11 C18 C23 C22 . . . . -176.7(4) ?
    C19 C18 C23 Cl2 . . . . 180.0(3) ?
    C11 C18 C23 Cl2 . . . . 3.2(4) ?
    N1 C11 C18' C19' . . . . -87.3(4) ?
    C10 C11 C18' C19' . . . . 69.2(4) ?
    C18 C11 C18' C19' . . . . 170.6(8) ?
    N1 C11 C18' C23' . . . . 97.4(5) ?
    C10 C11 C18' C23' . . . . -106.1(5) ?
    C18 C11 C18' C23' . . . . -4.7(5) ?
    C23' C18' C19' C20' . . . . 0.0 ?
    C11 C18' C19' C20' . . . . -175.4(5) ?
    C18' C19' C20' C21' . . . . 0.0 ?
    C19' C20' C21' C22' . . . . 0.0 ?
    C20' C21' C22' C23' . . . . 0.0 ?
    C21' C22' C23' C18' . . . . 0.0 ?
    C21' C22' C23' Cl2' . . . . 179.4(5) ?
    C19' C18' C23' C22' . . . . 0.0 ?
    C11 C18' C23' C22' . . . . 175.2(5) ?
    C19' C18' C23' Cl2' . . . . -179.4(5) ?
    C11 C18' C23' Cl2' . . . . -4.2(6) ?
