##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-06-27
_journal_date_accepted     2005-07-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      8
_journal_page_first     m1579
_journal_page_last     m1580
_journal_paper_category     EM
_journal_coeditor_code     XU6027
_publ_contact_author_name     'Prof. Hong-Xing Wang'
_publ_contact_author_address
;
Department of Chemistry
College of Sciences
Tianjin University
Tianjin, 300072
People's Republic of China
;
_publ_contact_author_email     liwenxuemei@hotmail.com
_publ_contact_author_fax     '86-22-27403475'
_publ_contact_author_phone     '86-22-27892355'
_publ_section_title
;
3-Chloro-N-ferrocenylmethyl-N-methylaniline
;
loop_
    _publ_author_name
    _publ_author_address
    'Ying-Jie Li'
;
Department of Chemistry
College of Sciences
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Hong-Xing Wang'
;
Department of Chemistry
College of Sciences
Tianjin University
Tianjin 300072
People's Republic of China
and
State Key Laboratory of Elemento-organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Hong-Fei Wu'
;
Department of Chemistry
College of Sciences
Tianjin University
Tianjin 300072
People's Republic of China
;
data_I
_chemical_name_systematic
;
3-Chloro-N-ferrocenylmethyl-N-methylaniline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H18 Cl Fe N'
_chemical_formula_sum     'C18 H18 Cl Fe N'
_chemical_formula_iupac     '[Fe (C5 H5) (C13 H13 Cl N)]'
_chemical_formula_weight     339.63
_chemical_melting_point     356
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.243(2)
_cell_length_b     10.250(3)
_cell_length_c     10.655(3)
_cell_angle_alpha     116.643(3)
_cell_angle_beta     92.658(3)
_cell_angle_gamma     106.771(3)
_cell_volume     754.0(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3182
_cell_measurement_theta_min     2.2
_cell_measurement_theta_max     27.7
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.496
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     352
_exptl_absorpt_coefficient_mu     1.169
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.501
_exptl_absorpt_correction_T_max     0.773
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 APEX-II CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4102
_diffrn_reflns_av_R_equivalents     0.0122
_diffrn_reflns_av_sigmaI/netI     0.0183
_diffrn_reflns_theta_min     2.2
_diffrn_reflns_theta_max     25.0
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     10
_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     2629
_reflns_number_gt     2421
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.028
_refine_ls_R_factor_gt     0.026
_refine_ls_wR_factor_gt     0.071
_refine_ls_wR_factor_ref     0.072
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.053
_refine_ls_number_reflns     2629
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0419P)²+0.2296P] 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     0.35
_refine_diff_density_min     -0.35
_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 0.12214(3) 0.31435(3) 0.23723(3) 0.03497(11) Uani d . 1 . . Fe
    Cl1 0.30560(8) 1.38747(6) 0.78932(6) 0.06204(17) Uani d . 1 . . Cl
    N1 0.2332(2) 0.82188(17) 0.45326(16) 0.0403(4) Uani d . 1 . . N
    C1 0.2899(3) 0.3222(2) 0.3894(2) 0.0482(5) Uani d . 1 . . C
    H1 0.3586 0.4155 0.4786 0.058 Uiso calc R 1 . . H
    C2 0.3413(3) 0.2655(3) 0.2557(3) 0.0560(5) Uani d . 1 . . C
    H2 0.4521 0.3115 0.2358 0.067 Uiso calc R 1 . . H
    C3 0.2047(3) 0.1284(3) 0.1565(2) 0.0568(6) Uani d . 1 . . C
    H3 0.2037 0.0634 0.0552 0.068 Uiso calc R 1 . . H
    C4 0.0702(3) 0.1022(2) 0.2281(2) 0.0493(5) Uani d . 1 . . C
    H4 -0.0410 0.0160 0.1853 0.059 Uiso calc R 1 . . H
    C5 0.1224(3) 0.2213(2) 0.3719(2) 0.0450(4) Uani d . 1 . . C
    H5 0.0541 0.2326 0.4465 0.054 Uiso calc R 1 . . H
    C6 -0.0268(2) 0.4515(2) 0.2975(2) 0.0430(4) Uani d . 1 . . C
    H6 -0.0809 0.4760 0.3814 0.052 Uiso calc R 1 . . H
    C7 -0.1022(3) 0.3238(2) 0.1583(3) 0.0568(6) Uani d . 1 . . C
    H7 -0.2174 0.2444 0.1288 0.068 Uiso calc R 1 . . H
    C8 0.0180(4) 0.3311(3) 0.0694(2) 0.0619(7) Uani d . 1 . . C
    H8 0.0008 0.2569 -0.0325 0.074 Uiso calc R 1 . . H
    C9 0.1684(3) 0.4621(2) 0.1526(2) 0.0498(5) Uani d . 1 . . C
    H9 0.2730 0.4949 0.1185 0.060 Uiso calc R 1 . . H
    C10 0.1417(2) 0.5376(2) 0.29490(19) 0.0376(4) Uani d . 1 . . C
    C11 0.2685(2) 0.6794(2) 0.4203(2) 0.0421(4) Uani d . 1 . . C
    H11A 0.2663 0.6643 0.5039 0.051 Uiso calc R 1 . . H
    H11B 0.3840 0.6915 0.4005 0.051 Uiso calc R 1 . . H
    C12 0.1766(3) 0.8424(2) 0.3348(2) 0.0490(5) Uani d . 1 . . C
    H12A 0.0776 0.8747 0.3503 0.074 Uiso calc R 1 . . H
    H12B 0.1460 0.7458 0.2471 0.074 Uiso calc R 1 . . H
    H12C 0.2685 0.9204 0.3284 0.074 Uiso calc R 1 . . H
    C13 0.3026(2) 0.9498(2) 0.58789(19) 0.0356(4) Uani d . 1 . . C
    C14 0.3931(3) 0.9450(2) 0.6996(2) 0.0476(5) Uani d . 1 . . C
    H14 0.4140 0.8545 0.6822 0.057 Uiso calc R 1 . . H
    C15 0.4515(3) 1.0727(3) 0.8351(2) 0.0553(5) Uani d . 1 . . C
    H15 0.5101 1.0657 0.9073 0.066 Uiso calc R 1 . . H
    C16 0.4259(3) 1.2104(3) 0.8667(2) 0.0527(5) Uani d . 1 . . C
    H16 0.4647 1.2955 0.9585 0.063 Uiso calc R 1 . . H
    C17 0.3409(2) 1.2162(2) 0.7569(2) 0.0424(4) Uani d . 1 . . C
    C18 0.2800(2) 1.0913(2) 0.6193(2) 0.0386(4) Uani d . 1 . . C
    H18 0.2243 1.1011 0.5477 0.046 Uiso calc R 1 . . H
_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 C2 . 2.032(2) ?
    Fe1 C10 . 2.0383(19) ?
    Fe1 C6 . 2.0386(19) ?
    Fe1 C1 . 2.0390(19) ?
    Fe1 C7 . 2.042(2) ?
    Fe1 C3 . 2.042(2) ?
    Fe1 C9 . 2.043(2) ?
    Fe1 C8 . 2.045(2) ?
    Fe1 C4 . 2.048(2) ?
    Fe1 C5 . 2.048(2) ?
    Cl1 C17 . 1.746(2) ?
    N1 C11 . 1.462(2) yes
    N1 C12 . 1.448(2) yes
    N1 C13 . 1.381(2) yes
    C1 C5 . 1.410(3) ?
    C1 C2 . 1.415(3) ?
    C1 H1 . 0.9800 ?
    C2 C3 . 1.416(3) ?
    C2 H2 . 0.9800 ?
    C3 C4 . 1.405(3) ?
    C3 H3 . 0.9800 ?
    C4 C5 . 1.407(3) ?
    C4 H4 . 0.9800 ?
    C5 H5 . 0.9800 ?
    C6 C7 . 1.416(3) ?
    C6 C10 . 1.424(3) ?
    C6 H6 . 0.9800 ?
    C7 C8 . 1.411(4) ?
    C7 H7 . 0.9800 ?
    C8 C9 . 1.413(3) ?
    C8 H8 . 0.9800 ?
    C9 C10 . 1.422(3) ?
    C9 H9 . 0.9800 ?
    C10 C11 . 1.498(3) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 C14 . 1.403(3) ?
    C13 C18 . 1.406(3) ?
    C14 C15 . 1.380(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.379(3) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.368(3) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.385(3) ?
    C18 H18 . 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
    C2 Fe1 C10 . . 119.18(9) ?
    C2 Fe1 C6 . . 154.15(10) ?
    C10 Fe1 C6 . . 40.89(8) ?
    C2 Fe1 C1 . . 40.69(9) ?
    C10 Fe1 C1 . . 107.49(8) ?
    C6 Fe1 C1 . . 119.85(8) ?
    C2 Fe1 C7 . . 163.68(10) ?
    C10 Fe1 C7 . . 68.61(8) ?
    C6 Fe1 C7 . . 40.60(8) ?
    C1 Fe1 C7 . . 154.43(10) ?
    C2 Fe1 C3 . . 40.66(10) ?
    C10 Fe1 C3 . . 154.15(10) ?
    C6 Fe1 C3 . . 163.80(9) ?
    C1 Fe1 C3 . . 68.03(9) ?
    C7 Fe1 C3 . . 126.58(9) ?
    C2 Fe1 C9 . . 107.46(9) ?
    C10 Fe1 C9 . . 40.77(8) ?
    C6 Fe1 C9 . . 68.41(9) ?
    C1 Fe1 C9 . . 126.27(9) ?
    C7 Fe1 C9 . . 68.25(10) ?
    C3 Fe1 C9 . . 119.95(9) ?
    C2 Fe1 C8 . . 126.30(10) ?
    C10 Fe1 C8 . . 68.34(8) ?
    C6 Fe1 C8 . . 68.08(9) ?
    C1 Fe1 C8 . . 163.68(11) ?
    C7 Fe1 C8 . . 40.41(10) ?
    C3 Fe1 C8 . . 108.40(9) ?
    C9 Fe1 C8 . . 40.43(10) ?
    C2 Fe1 C4 . . 68.12(9) ?
    C10 Fe1 C4 . . 163.86(8) ?
    C6 Fe1 C4 . . 126.72(9) ?
    C1 Fe1 C4 . . 67.83(8) ?
    C7 Fe1 C4 . . 108.51(9) ?
    C3 Fe1 C4 . . 40.19(9) ?
    C9 Fe1 C4 . . 154.39(9) ?
    C8 Fe1 C4 . . 120.49(9) ?
    C2 Fe1 C5 . . 68.18(9) ?
    C10 Fe1 C5 . . 126.39(8) ?
    C6 Fe1 C5 . . 108.26(8) ?
    C1 Fe1 C5 . . 40.37(8) ?
    C7 Fe1 C5 . . 120.33(10) ?
    C3 Fe1 C5 . . 67.70(9) ?
    C9 Fe1 C5 . . 163.74(9) ?
    C8 Fe1 C5 . . 154.65(10) ?
    C4 Fe1 C5 . . 40.20(8) ?
    C11 N1 C12 . . 118.18(15) yes
    C11 N1 C13 . . 119.21(15) yes
    C12 N1 C13 . . 119.61(15) yes
    C5 C1 C2 . . 108.06(19) ?
    C5 C1 Fe1 . . 70.15(11) ?
    C2 C1 Fe1 . . 69.41(12) ?
    C5 C1 H1 . . 126.0 ?
    C2 C1 H1 . . 126.0 ?
    Fe1 C1 H1 . . 126.0 ?
    C1 C2 C3 . . 107.5(2) ?
    C1 C2 Fe1 . . 69.90(11) ?
    C3 C2 Fe1 . . 70.03(12) ?
    C1 C2 H2 . . 126.3 ?
    C3 C2 H2 . . 126.3 ?
    Fe1 C2 H2 . . 126.3 ?
    C4 C3 C2 . . 108.21(19) ?
    C4 C3 Fe1 . . 70.12(11) ?
    C2 C3 Fe1 . . 69.31(12) ?
    C4 C3 H3 . . 125.9 ?
    C2 C3 H3 . . 125.9 ?
    Fe1 C3 H3 . . 125.9 ?
    C3 C4 C5 . . 108.18(19) ?
    C3 C4 Fe1 . . 69.69(12) ?
    C5 C4 Fe1 . . 69.91(11) ?
    C3 C4 H4 . . 125.9 ?
    C5 C4 H4 . . 125.9 ?
    Fe1 C4 H4 . . 125.9 ?
    C4 C5 C1 . . 108.05(19) ?
    C4 C5 Fe1 . . 69.89(11) ?
    C1 C5 Fe1 . . 69.48(11) ?
    C4 C5 H5 . . 126.0 ?
    C1 C5 H5 . . 126.0 ?
    Fe1 C5 H5 . . 126.0 ?
    C7 C6 C10 . . 108.14(19) ?
    C7 C6 Fe1 . . 69.82(12) ?
    C10 C6 Fe1 . . 69.54(10) ?
    C7 C6 H6 . . 125.9 ?
    C10 C6 H6 . . 125.9 ?
    Fe1 C6 H6 . . 125.9 ?
    C8 C7 C6 . . 107.9(2) ?
    C8 C7 Fe1 . . 69.90(13) ?
    C6 C7 Fe1 . . 69.58(11) ?
    C8 C7 H7 . . 126.0 ?
    C6 C7 H7 . . 126.0 ?
    Fe1 C7 H7 . . 126.0 ?
    C7 C8 C9 . . 108.48(19) ?
    C7 C8 Fe1 . . 69.69(12) ?
    C9 C8 Fe1 . . 69.73(12) ?
    C7 C8 H8 . . 125.8 ?
    C9 C8 H8 . . 125.8 ?
    Fe1 C8 H8 . . 125.8 ?
    C8 C9 C10 . . 108.0(2) ?
    C8 C9 Fe1 . . 69.84(12) ?
    C10 C9 Fe1 . . 69.43(11) ?
    C8 C9 H9 . . 126.0 ?
    C10 C9 H9 . . 126.0 ?
    Fe1 C9 H9 . . 126.0 ?
    C9 C10 C6 . . 107.46(18) ?
    C9 C10 C11 . . 126.55(19) ?
    C6 C10 C11 . . 125.98(17) ?
    C9 C10 Fe1 . . 69.80(11) ?
    C6 C10 Fe1 . . 69.57(10) ?
    C11 C10 Fe1 . . 124.89(13) ?
    N1 C11 C10 . . 113.31(15) ?
    N1 C11 H11A . . 108.9 ?
    C10 C11 H11A . . 108.9 ?
    N1 C11 H11B . . 108.9 ?
    C10 C11 H11B . . 108.9 ?
    H11A C11 H11B . . 107.7 ?
    N1 C12 H12A . . 109.5 ?
    N1 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    N1 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    N1 C13 C14 . . 122.67(16) ?
    N1 C13 C18 . . 120.31(16) ?
    C14 C13 C18 . . 117.00(17) ?
    C15 C14 C13 . . 120.93(18) ?
    C15 C14 H14 . . 119.5 ?
    C13 C14 H14 . . 119.5 ?
    C16 C15 C14 . . 122.05(19) ?
    C16 C15 H15 . . 119.0 ?
    C14 C15 H15 . . 119.0 ?
    C17 C16 C15 . . 117.02(18) ?
    C17 C16 H16 . . 121.5 ?
    C15 C16 H16 . . 121.5 ?
    C16 C17 C18 . . 123.07(18) ?
    C16 C17 Cl1 . . 119.38(15) ?
    C18 C17 Cl1 . . 117.55(16) ?
    C17 C18 C13 . . 119.90(18) ?
    C17 C18 H18 . . 120.1 ?
    C13 C18 H18 . . 120.1 ?
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
    C2 Fe1 C1 C5 . . . . -119.19(18) ?
    C10 Fe1 C1 C5 . . . . 126.13(12) ?
    C6 Fe1 C1 C5 . . . . 83.27(14) ?
    C7 Fe1 C1 C5 . . . . 49.3(2) ?
    C3 Fe1 C1 C5 . . . . -80.96(14) ?
    C9 Fe1 C1 C5 . . . . 167.23(11) ?
    C8 Fe1 C1 C5 . . . . -161.4(3) ?
    C4 Fe1 C1 C5 . . . . -37.43(12) ?
    C10 Fe1 C1 C2 . . . . -114.68(14) ?
    C6 Fe1 C1 C2 . . . . -157.54(13) ?
    C7 Fe1 C1 C2 . . . . 168.47(18) ?
    C3 Fe1 C1 C2 . . . . 38.23(14) ?
    C9 Fe1 C1 C2 . . . . -73.58(16) ?
    C8 Fe1 C1 C2 . . . . -42.2(3) ?
    C4 Fe1 C1 C2 . . . . 81.76(15) ?
    C5 Fe1 C1 C2 . . . . 119.19(18) ?
    C5 C1 C2 C3 . . . . -0.5(2) ?
    Fe1 C1 C2 C3 . . . . -60.23(14) ?
    C5 C1 C2 Fe1 . . . . 59.74(14) ?
    C10 Fe1 C2 C1 . . . . 83.03(14) ?
    C6 Fe1 C2 C1 . . . . 49.5(2) ?
    C7 Fe1 C2 C1 . . . . -162.1(3) ?
    C3 Fe1 C2 C1 . . . . -118.25(19) ?
    C9 Fe1 C2 C1 . . . . 125.84(13) ?
    C8 Fe1 C2 C1 . . . . 166.46(13) ?
    C4 Fe1 C2 C1 . . . . -80.99(14) ?
    C5 Fe1 C2 C1 . . . . -37.52(13) ?
    C10 Fe1 C2 C3 . . . . -158.72(13) ?
    C6 Fe1 C2 C3 . . . . 167.72(17) ?
    C1 Fe1 C2 C3 . . . . 118.25(19) ?
    C7 Fe1 C2 C3 . . . . -43.9(4) ?
    C9 Fe1 C2 C3 . . . . -115.91(14) ?
    C8 Fe1 C2 C3 . . . . -75.29(17) ?
    C4 Fe1 C2 C3 . . . . 37.27(14) ?
    C5 Fe1 C2 C3 . . . . 80.73(14) ?
    C1 C2 C3 C4 . . . . 0.6(2) ?
    Fe1 C2 C3 C4 . . . . -59.53(14) ?
    C1 C2 C3 Fe1 . . . . 60.15(14) ?
    C2 Fe1 C3 C4 . . . . 119.46(19) ?
    C10 Fe1 C3 C4 . . . . 166.08(16) ?
    C6 Fe1 C3 C4 . . . . -41.1(3) ?
    C1 Fe1 C3 C4 . . . . 81.20(14) ?
    C7 Fe1 C3 C4 . . . . -74.58(16) ?
    C9 Fe1 C3 C4 . . . . -158.54(13) ?
    C8 Fe1 C3 C4 . . . . -115.78(14) ?
    C5 Fe1 C3 C4 . . . . 37.47(12) ?
    C10 Fe1 C3 C2 . . . . 46.6(2) ?
    C6 Fe1 C3 C2 . . . . -160.6(3) ?
    C1 Fe1 C3 C2 . . . . -38.26(13) ?
    C7 Fe1 C3 C2 . . . . 165.96(14) ?
    C9 Fe1 C3 C2 . . . . 81.99(16) ?
    C8 Fe1 C3 C2 . . . . 124.76(15) ?
    C4 Fe1 C3 C2 . . . . -119.46(19) ?
    C5 Fe1 C3 C2 . . . . -82.00(14) ?
    C2 C3 C4 C5 . . . . -0.5(2) ?
    Fe1 C3 C4 C5 . . . . -59.53(13) ?
    C2 C3 C4 Fe1 . . . . 59.03(14) ?
    C2 Fe1 C4 C3 . . . . -37.68(14) ?
    C10 Fe1 C4 C3 . . . . -157.8(3) ?
    C6 Fe1 C4 C3 . . . . 166.76(12) ?
    C1 Fe1 C4 C3 . . . . -81.74(14) ?
    C7 Fe1 C4 C3 . . . . 125.29(14) ?
    C9 Fe1 C4 C3 . . . . 47.2(3) ?
    C8 Fe1 C4 C3 . . . . 82.57(16) ?
    C5 Fe1 C4 C3 . . . . -119.32(18) ?
    C2 Fe1 C4 C5 . . . . 81.63(14) ?
    C10 Fe1 C4 C5 . . . . -38.5(3) ?
    C6 Fe1 C4 C5 . . . . -73.92(15) ?
    C1 Fe1 C4 C5 . . . . 37.58(12) ?
    C7 Fe1 C4 C5 . . . . -115.40(14) ?
    C3 Fe1 C4 C5 . . . . 119.32(18) ?
    C9 Fe1 C4 C5 . . . . 166.48(19) ?
    C8 Fe1 C4 C5 . . . . -158.11(14) ?
    C3 C4 C5 C1 . . . . 0.2(2) ?
    Fe1 C4 C5 C1 . . . . -59.20(13) ?
    C3 C4 C5 Fe1 . . . . 59.39(14) ?
    C2 C1 C5 C4 . . . . 0.2(2) ?
    Fe1 C1 C5 C4 . . . . 59.46(13) ?
    C2 C1 C5 Fe1 . . . . -59.27(14) ?
    C2 Fe1 C5 C4 . . . . -81.49(14) ?
    C10 Fe1 C5 C4 . . . . 167.58(12) ?
    C6 Fe1 C5 C4 . . . . 125.80(13) ?
    C1 Fe1 C5 C4 . . . . -119.30(18) ?
    C7 Fe1 C5 C4 . . . . 82.96(14) ?
    C3 Fe1 C5 C4 . . . . -37.46(13) ?
    C9 Fe1 C5 C4 . . . . -158.9(3) ?
    C8 Fe1 C5 C4 . . . . 48.6(3) ?
    C2 Fe1 C5 C1 . . . . 37.81(13) ?
    C10 Fe1 C5 C1 . . . . -73.12(14) ?
    C6 Fe1 C5 C1 . . . . -114.90(13) ?
    C7 Fe1 C5 C1 . . . . -157.73(12) ?
    C3 Fe1 C5 C1 . . . . 81.84(14) ?
    C9 Fe1 C5 C1 . . . . -39.5(3) ?
    C8 Fe1 C5 C1 . . . . 167.91(19) ?
    C4 Fe1 C5 C1 . . . . 119.30(18) ?
    C2 Fe1 C6 C7 . . . . 166.92(19) ?
    C10 Fe1 C6 C7 . . . . 119.41(18) ?
    C1 Fe1 C6 C7 . . . . -158.24(14) ?
    C3 Fe1 C6 C7 . . . . -42.9(3) ?
    C9 Fe1 C6 C7 . . . . 81.33(15) ?
    C8 Fe1 C6 C7 . . . . 37.65(14) ?
    C4 Fe1 C6 C7 . . . . -74.83(16) ?
    C5 Fe1 C6 C7 . . . . -115.61(14) ?
    C2 Fe1 C6 C10 . . . . 47.5(2) ?
    C1 Fe1 C6 C10 . . . . 82.35(13) ?
    C7 Fe1 C6 C10 . . . . -119.41(18) ?
    C3 Fe1 C6 C10 . . . . -162.3(3) ?
    C9 Fe1 C6 C10 . . . . -38.08(11) ?
    C8 Fe1 C6 C10 . . . . -81.77(13) ?
    C4 Fe1 C6 C10 . . . . 165.76(11) ?
    C5 Fe1 C6 C10 . . . . 124.98(11) ?
    C10 C6 C7 C8 . . . . -0.4(2) ?
    Fe1 C6 C7 C8 . . . . -59.62(14) ?
    C10 C6 C7 Fe1 . . . . 59.19(13) ?
    C2 Fe1 C7 C8 . . . . -40.4(4) ?
    C10 Fe1 C7 C8 . . . . 81.29(13) ?
    C6 Fe1 C7 C8 . . . . 119.06(18) ?
    C1 Fe1 C7 C8 . . . . 167.23(17) ?
    C3 Fe1 C7 C8 . . . . -74.61(16) ?
    C9 Fe1 C7 C8 . . . . 37.30(13) ?
    C4 Fe1 C7 C8 . . . . -115.61(13) ?
    C5 Fe1 C7 C8 . . . . -158.11(12) ?
    C2 Fe1 C7 C6 . . . . -159.5(3) ?
    C10 Fe1 C7 C6 . . . . -37.77(12) ?
    C1 Fe1 C7 C6 . . . . 48.2(2) ?
    C3 Fe1 C7 C6 . . . . 166.33(12) ?
    C9 Fe1 C7 C6 . . . . -81.76(13) ?
    C8 Fe1 C7 C6 . . . . -119.06(18) ?
    C4 Fe1 C7 C6 . . . . 125.33(13) ?
    C5 Fe1 C7 C6 . . . . 82.83(14) ?
    C6 C7 C8 C9 . . . . 0.3(2) ?
    Fe1 C7 C8 C9 . . . . -59.12(15) ?
    C6 C7 C8 Fe1 . . . . 59.42(14) ?
    C2 Fe1 C8 C7 . . . . 166.94(13) ?
    C10 Fe1 C8 C7 . . . . -82.01(13) ?
    C6 Fe1 C8 C7 . . . . -37.82(12) ?
    C1 Fe1 C8 C7 . . . . -160.2(3) ?
    C3 Fe1 C8 C7 . . . . 125.32(14) ?
    C9 Fe1 C8 C7 . . . . -119.80(18) ?
    C4 Fe1 C8 C7 . . . . 82.91(15) ?
    C5 Fe1 C8 C7 . . . . 48.7(2) ?
    C2 Fe1 C8 C9 . . . . -73.26(16) ?
    C10 Fe1 C8 C9 . . . . 37.79(13) ?
    C6 Fe1 C8 C9 . . . . 81.98(14) ?
    C1 Fe1 C8 C9 . . . . -40.4(4) ?
    C7 Fe1 C8 C9 . . . . 119.80(18) ?
    C3 Fe1 C8 C9 . . . . -114.88(14) ?
    C4 Fe1 C8 C9 . . . . -157.29(13) ?
    C5 Fe1 C8 C9 . . . . 168.52(17) ?
    C7 C8 C9 C10 . . . . 0.0(2) ?
    Fe1 C8 C9 C10 . . . . -59.14(14) ?
    C7 C8 C9 Fe1 . . . . 59.09(15) ?
    C2 Fe1 C9 C8 . . . . 125.99(15) ?
    C10 Fe1 C9 C8 . . . . -119.3(2) ?
    C6 Fe1 C9 C8 . . . . -81.12(15) ?
    C1 Fe1 C9 C8 . . . . 166.96(14) ?
    C7 Fe1 C9 C8 . . . . -37.27(14) ?
    C3 Fe1 C9 C8 . . . . 83.43(17) ?
    C4 Fe1 C9 C8 . . . . 50.3(3) ?
    C5 Fe1 C9 C8 . . . . -162.3(3) ?
    C2 Fe1 C9 C10 . . . . -114.70(13) ?
    C6 Fe1 C9 C10 . . . . 38.19(12) ?
    C1 Fe1 C9 C10 . . . . -73.74(15) ?
    C7 Fe1 C9 C10 . . . . 82.03(13) ?
    C3 Fe1 C9 C10 . . . . -157.26(13) ?
    C8 Fe1 C9 C10 . . . . 119.3(2) ?
    C4 Fe1 C9 C10 . . . . 169.63(17) ?
    C5 Fe1 C9 C10 . . . . -43.0(3) ?
    C8 C9 C10 C6 . . . . -0.2(2) ?
    Fe1 C9 C10 C6 . . . . -59.62(12) ?
    C8 C9 C10 C11 . . . . 178.48(18) ?
    Fe1 C9 C10 C11 . . . . 119.08(18) ?
    C8 C9 C10 Fe1 . . . . 59.40(14) ?
    C7 C6 C10 C9 . . . . 0.4(2) ?
    Fe1 C6 C10 C9 . . . . 59.77(13) ?
    C7 C6 C10 C11 . . . . -178.30(17) ?
    Fe1 C6 C10 C11 . . . . -118.94(18) ?
    C7 C6 C10 Fe1 . . . . -59.36(13) ?
    C2 Fe1 C10 C9 . . . . 83.03(15) ?
    C6 Fe1 C10 C9 . . . . -118.57(17) ?
    C1 Fe1 C10 C9 . . . . 125.76(14) ?
    C7 Fe1 C10 C9 . . . . -81.07(15) ?
    C3 Fe1 C10 C9 . . . . 50.2(2) ?
    C8 Fe1 C10 C9 . . . . -37.48(15) ?
    C4 Fe1 C10 C9 . . . . -163.8(3) ?
    C5 Fe1 C10 C9 . . . . 166.29(13) ?
    C2 Fe1 C10 C6 . . . . -158.39(12) ?
    C1 Fe1 C10 C6 . . . . -115.67(12) ?
    C7 Fe1 C10 C6 . . . . 37.50(13) ?
    C3 Fe1 C10 C6 . . . . 168.76(17) ?
    C9 Fe1 C10 C6 . . . . 118.57(17) ?
    C8 Fe1 C10 C6 . . . . 81.09(14) ?
    C4 Fe1 C10 C6 . . . . -45.2(3) ?
    C5 Fe1 C10 C6 . . . . -75.14(14) ?
    C2 Fe1 C10 C11 . . . . -38.10(19) ?
    C6 Fe1 C10 C11 . . . . 120.3(2) ?
    C1 Fe1 C10 C11 . . . . 4.63(18) ?
    C7 Fe1 C10 C11 . . . . 157.80(19) ?
    C3 Fe1 C10 C11 . . . . -70.9(3) ?
    C9 Fe1 C10 C11 . . . . -121.1(2) ?
    C8 Fe1 C10 C11 . . . . -158.6(2) ?
    C4 Fe1 C10 C11 . . . . 75.1(3) ?
    C5 Fe1 C10 C11 . . . . 45.2(2) ?
    C13 N1 C11 C10 . . . . 160.19(16) ?
    C12 N1 C11 C10 . . . . -39.5(2) ?
    C9 C10 C11 N1 . . . . 101.4(2) ?
    C6 C10 C11 N1 . . . . -80.2(2) ?
    Fe1 C10 C11 N1 . . . . -169.03(13) ?
    C12 N1 C13 C14 . . . . -166.08(19) ?
    C11 N1 C13 C14 . . . . -6.0(3) ?
    C12 N1 C13 C18 . . . . 15.8(3) ?
    C11 N1 C13 C18 . . . . 175.84(17) ?
    N1 C13 C14 C15 . . . . -176.10(19) ?
    C18 C13 C14 C15 . . . . 2.1(3) ?
    C13 C14 C15 C16 . . . . -0.7(4) ?
    C14 C15 C16 C17 . . . . -0.7(3) ?
    C15 C16 C17 C18 . . . . 0.6(3) ?
    C15 C16 C17 Cl1 . . . . -179.52(17) ?
    C16 C17 C18 C13 . . . . 0.9(3) ?
    Cl1 C17 C18 C13 . . . . -179.01(14) ?
    N1 C13 C18 C17 . . . . 176.07(17) ?
    C14 C13 C18 C17 . . . . -2.2(3) ?
