##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-08-26
_journal_date_accepted     2012-09-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue     10
_journal_page_first     m1318
_journal_page_last     m1318
_journal_paper_category     QM
_journal_paper_doi     10.1107/S1600536812039177
_journal_coeditor_code     ZQ2180
_publ_contact_author_name     'Touhami, Lanez'
_publ_contact_author_address
;
VTRS laboratory,
Institute of sciences and technology,
university of El-Oued,
PO Box 789
El-Oued 39000,
Algeria
;
_publ_contact_author_email     'lanezt@gmail.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
N-Ferrocenylmethyl-2-nitroaniline
;
loop_
    _publ_author_name
    _publ_author_address
    'Rahim, Oumelkheir'
;
Department of Chemistry,
University of Ouargla,
PO Box 511
Ouargla 30000,
Algeria
;
    'Khelef, Abdelhamid'
;
Department of Sciences and Technology,
University Mohamed Khider of Biskra,
PO Box 145
Biskra 07000,
Algeria
;
    'Terki, Belgacem'
;
Department of Chemistry,
University of Ouargla,
PO Box 511
Ouargla 30000,
Algeria
;
    'Mahboub, Mohammed Sadok'
;
VTRS Laboratory,
Institute of Sciences and Technology,
University of El-Oued,
PO Box 789
El-Oued 39000,
Algeria
;
    'Lanez, Touhami'
;
VTRS Laboratory,
Institute of Sciences and Technology,
University of El-Oued,
PO Box 789
El-Oued 39000,
Algeria
;
data_I
_chemical_name_systematic
;
N-Ferrocenylmethyl-2-nitroaniline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H16 Fe N2 O2'
_chemical_formula_sum     'C17 H16 Fe N2 O2'
_chemical_formula_structural     'C17 H16 Fe N2 O2'
_chemical_formula_analytical     ?
_chemical_formula_iupac     '[Fe (C5 H5) (C12 H11 N2 O2)]'
_chemical_formula_weight     336.17
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/a'
_symmetry_space_group_name_Hall     '-P 2yab'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,1/2+y,-z
    3 -x,-y,-z
    4 1/2+x,1/2-y,z
_cell_length_a     10.3609(3)
_cell_length_b     7.8700(2)
_cell_length_c     17.7948(7)
_cell_angle_alpha     90
_cell_angle_beta     93.043(2)
_cell_angle_gamma     90
_cell_volume     1448.95(8)
_cell_formula_units_Z     4
_cell_measurement_theta_min     1.15
_cell_measurement_theta_max     27.36
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.1
_exptl_crystal_size_min     0.1
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.541
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     696
_exptl_absorpt_coefficient_mu     1.049
_exptl_absorpt_correction_type     none
_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     'Nonius KappaCCD'
_diffrn_measurement_method     'CCD'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     14651
_diffrn_reflns_av_R_equivalents     0.028
_diffrn_reflns_theta_min     1.15
_diffrn_reflns_theta_max     27.36
_diffrn_reflns_theta_full     27.36
_diffrn_measured_fraction_theta_max     0.978
_diffrn_measured_fraction_theta_full     0.978
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_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 >
σ(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     3204
_reflns_number_gt     2881
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0286
_refine_ls_R_factor_gt     0.0251
_refine_ls_wR_factor_gt     0.0666
_refine_ls_wR_factor_ref     0.0692
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.048
_refine_ls_number_reflns     3204
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0381P)²+0.5817P] 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     0.404
_refine_diff_density_min     -0.252
_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 0 '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 0.006 '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     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Fe Fe 0.175327(16) 0.49618(2) 0.136596(10) 0.01155(8) Uani d . 1 1 . .
    O O1 -0.08310(11) -0.31659(13) 0.38282(7) 0.0288(3) Uani d . 1 1 . .
    O O2 0.09259(10) -0.23198(13) 0.33170(7) 0.0277(3) Uani d . 1 1 . .
    N N1 0.13730(11) 0.09690(15) 0.31440(7) 0.0173(2) Uani d . 1 1 . .
    N N2 -0.00760(11) -0.20171(15) 0.36602(7) 0.0190(2) Uani d . 1 1 . .
    C C1 0.34295(12) 0.55527(19) 0.08304(8) 0.0196(3) Uani d . 1 1 . .
    H H1 0.3849 0.4876 0.0491 0.024 Uiso calc R 1 1 . .
    C C2 0.24330(13) 0.67691(19) 0.06407(9) 0.0219(3) Uani d . 1 1 . .
    H H2 0.2089 0.7022 0.0160 0.026 Uiso calc R 1 1 . .
    C C3 0.20652(13) 0.75263(18) 0.13377(10) 0.0244(3) Uani d . 1 1 . .
    H H3 0.1437 0.8360 0.1382 0.029 Uiso calc R 1 1 . .
    C C4 0.28328(13) 0.67775(19) 0.19565(9) 0.0224(3) Uani d . 1 1 . .
    H H4 0.2788 0.7042 0.2464 0.027 Uiso calc R 1 1 . .
    C C5 0.36735(12) 0.55548(19) 0.16420(9) 0.0195(3) Uani d . 1 1 . .
    H H5 0.4272 0.4879 0.1911 0.023 Uiso calc R 1 1 . .
    C C6 0.13517(12) 0.24086(17) 0.12877(8) 0.0155(3) Uani d . 1 1 . .
    H H6 0.1914 0.1558 0.1147 0.019 Uiso calc R 1 1 . .
    C C7 0.04727(12) 0.33367(17) 0.07798(8) 0.0163(3) Uani d . 1 1 . .
    H H7 0.0373 0.3199 0.0261 0.020 Uiso calc R 1 1 . .
    C C8 -0.02175(12) 0.45125(18) 0.12293(8) 0.0162(3) Uani d . 1 1 . .
    H H8 -0.0848 0.5271 0.1049 0.019 Uiso calc R 1 1 . .
    C C9 0.02341(11) 0.43195(17) 0.20148(8) 0.0153(3) Uani d . 1 1 . .
    H H9 -0.0059 0.4929 0.2420 0.018 Uiso calc R 1 1 . .
    C C10 0.12191(11) 0.30137(16) 0.20541(8) 0.0144(3) Uani d . 1 1 . .
    C C11 0.19956(12) 0.23941(18) 0.27600(8) 0.0173(3) Uani d . 1 1 . .
    H H11A 0.2846 0.2037 0.2619 0.021 Uiso calc R 1 1 . .
    H H11B 0.2111 0.3334 0.3110 0.021 Uiso calc R 1 1 . .
    C C12 0.03771(12) 0.11221(16) 0.36170(7) 0.0141(3) Uani d . 1 1 . .
    C C13 -0.00039(12) 0.27404(17) 0.38947(8) 0.0161(3) Uani d . 1 1 . .
    H H13 0.0417 0.3709 0.3735 0.019 Uiso calc R 1 1 . .
    C C14 -0.09834(13) 0.29185(17) 0.43954(8) 0.0181(3) Uani d . 1 1 . .
    H H14 -0.1180 0.3994 0.4573 0.022 Uiso calc R 1 1 . .
    C C15 -0.16826(13) 0.15031(18) 0.46392(8) 0.0201(3) Uani d . 1 1 . .
    H H15 -0.2335 0.1634 0.4974 0.024 Uiso calc R 1 1 . .
    C C16 -0.13745(14) -0.00804(16) 0.43693(9) 0.0191(3) Uani d . 1 1 . .
    H H16 -0.1841 -0.1025 0.4514 0.023 Uiso calc R 1 1 . .
    C C17 -0.03569(13) -0.02881(17) 0.38750(8) 0.0157(3) Uani d . 1 1 . .
    H H10 0.1571(19) -0.001(2) 0.3026(12) 0.028(5) Uiso d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Fe C3 . 2.0450(14) ?
    Fe C6 . 2.0552(13) ?
    Fe C10 . 2.0562(13) ?
    Fe C9 . 2.0638(12) ?
    Fe C4 . 2.0669(14) ?
    Fe C2 . 2.0691(14) ?
    Fe C8 . 2.0738(12) ?
    Fe C5 . 2.0769(13) ?
    Fe C1 . 2.0776(13) ?
    Fe C7 . 2.0826(13) ?
    O1 N2 . 1.2423(15) ?
    O2 N2 . 1.2549(15) ?
    N1 C12 . 1.3711(17) ?
    N1 C11 . 1.4790(17) ?
    N1 H10 . 0.830(18) ?
    N2 C17 . 1.4471(17) ?
    C1 C2 . 1.435(2) ?
    C1 C5 . 1.453(2) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.445(2) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.449(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.432(2) ?
    C4 H4 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.4466(19) ?
    C6 C10 . 1.4579(19) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.4382(19) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.458(2) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.4474(18) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.5348(18) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.4292(18) ?
    C12 C17 . 1.4346(18) ?
    C13 C14 . 1.3926(19) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.4096(19) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.3790(19) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.4179(19) ?
    C16 H16 . 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
    C3 Fe C6 . . 174.23(6) ?
    C3 Fe C10 . . 142.98(6) ?
    C6 Fe C10 . . 41.54(5) ?
    C3 Fe C9 . . 112.44(6) ?
    C6 Fe C9 . . 68.95(5) ?
    C10 Fe C9 . . 41.13(5) ?
    C3 Fe C4 . . 41.26(6) ?
    C6 Fe C4 . . 144.34(6) ?
    C10 Fe C4 . . 111.60(6) ?
    C9 Fe C4 . . 107.04(6) ?
    C3 Fe C2 . . 41.13(6) ?
    C6 Fe C2 . . 134.76(6) ?
    C10 Fe C2 . . 174.42(5) ?
    C9 Fe C2 . . 144.32(6) ?
    C4 Fe C2 . . 69.45(6) ?
    C3 Fe C8 . . 108.74(6) ?
    C6 Fe C8 . . 68.34(5) ?
    C10 Fe C8 . . 69.41(5) ?
    C9 Fe C8 . . 41.27(5) ?
    C4 Fe C8 . . 132.87(6) ?
    C2 Fe C8 . . 114.18(5) ?
    C3 Fe C5 . . 68.49(6) ?
    C6 Fe C5 . . 115.06(6) ?
    C10 Fe C5 . . 108.15(5) ?
    C9 Fe C5 . . 132.24(6) ?
    C4 Fe C5 . . 40.42(6) ?
    C2 Fe C5 . . 68.87(6) ?
    C8 Fe C5 . . 172.26(6) ?
    C3 Fe C1 . . 68.33(6) ?
    C6 Fe C1 . . 111.03(5) ?
    C10 Fe C1 . . 134.27(5) ?
    C9 Fe C1 . . 172.94(6) ?
    C4 Fe C1 . . 68.62(6) ?
    C2 Fe C1 . . 40.50(6) ?
    C8 Fe C1 . . 145.71(6) ?
    C5 Fe C1 . . 40.94(6) ?
    C3 Fe C7 . . 133.71(6) ?
    C6 Fe C7 . . 40.92(5) ?
    C10 Fe C7 . . 69.88(5) ?
    C9 Fe C7 . . 69.22(5) ?
    C4 Fe C7 . . 172.91(5) ?
    C2 Fe C7 . . 109.79(6) ?
    C8 Fe C7 . . 40.49(5) ?
    C5 Fe C7 . . 146.44(6) ?
    C1 Fe C7 . . 115.69(6) ?
    C12 N1 C11 . . 125.30(12) ?
    C12 N1 H10 . . 116.2(13) ?
    C11 N1 H10 . . 118.1(13) ?
    O1 N2 O2 . . 121.78(12) ?
    O1 N2 C17 . . 118.86(11) ?
    O2 N2 C17 . . 119.36(11) ?
    C2 C1 C5 . . 108.55(12) ?
    C2 C1 Fe . . 69.43(7) ?
    C5 C1 Fe . . 69.51(7) ?
    C2 C1 H1 . . 125.7 ?
    C5 C1 H1 . . 125.7 ?
    Fe C1 H1 . . 126.9 ?
    C1 C2 C3 . . 107.00(13) ?
    C1 C2 Fe . . 70.07(8) ?
    C3 C2 Fe . . 68.54(8) ?
    C1 C2 H2 . . 126.5 ?
    C3 C2 H2 . . 126.5 ?
    Fe C2 H2 . . 126.4 ?
    C2 C3 C4 . . 108.99(12) ?
    C2 C3 Fe . . 70.33(8) ?
    C4 C3 Fe . . 70.18(8) ?
    C2 C3 H3 . . 125.5 ?
    C4 C3 H3 . . 125.5 ?
    Fe C3 H3 . . 125.6 ?
    C5 C4 C3 . . 107.29(13) ?
    C5 C4 Fe . . 70.17(8) ?
    C3 C4 Fe . . 68.56(8) ?
    C5 C4 H4 . . 126.4 ?
    C3 C4 H4 . . 126.4 ?
    Fe C4 H4 . . 126.5 ?
    C4 C5 C1 . . 108.18(13) ?
    C4 C5 Fe . . 69.41(7) ?
    C1 C5 Fe . . 69.55(7) ?
    C4 C5 H5 . . 125.9 ?
    C1 C5 H5 . . 125.9 ?
    Fe C5 H5 . . 126.7 ?
    C7 C6 C10 . . 109.39(11) ?
    C7 C6 Fe . . 70.56(7) ?
    C10 C6 Fe . . 69.27(7) ?
    C7 C6 H6 . . 125.3 ?
    C10 C6 H6 . . 125.3 ?
    Fe C6 H6 . . 126.5 ?
    C8 C7 C6 . . 107.01(12) ?
    C8 C7 Fe . . 69.43(7) ?
    C6 C7 Fe . . 68.52(7) ?
    C8 C7 H7 . . 126.5 ?
    C6 C7 H7 . . 126.5 ?
    Fe C7 H7 . . 127.1 ?
    C7 C8 C9 . . 108.81(12) ?
    C7 C8 Fe . . 70.09(7) ?
    C9 C8 Fe . . 69.00(7) ?
    C7 C8 H8 . . 125.6 ?
    C9 C8 H8 . . 125.6 ?
    Fe C8 H8 . . 126.9 ?
    C10 C9 C8 . . 108.04(12) ?
    C10 C9 Fe . . 69.15(7) ?
    C8 C9 Fe . . 69.73(7) ?
    C10 C9 H9 . . 126.0 ?
    C8 C9 H9 . . 126.0 ?
    Fe C9 H9 . . 126.7 ?
    C9 C10 C6 . . 106.74(11) ?
    C9 C10 C11 . . 127.06(12) ?
    C6 C10 C11 . . 126.19(11) ?
    C9 C10 Fe . . 69.71(7) ?
    C6 C10 Fe . . 69.19(7) ?
    C11 C10 Fe . . 125.33(8) ?
    N1 C11 C10 . . 113.36(10) ?
    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 C13 . . 121.41(12) ?
    N1 C12 C17 . . 123.88(12) ?
    C13 C12 C17 . . 114.71(11) ?
    C14 C13 C12 . . 122.34(12) ?
    C14 C13 H13 . . 118.8 ?
    C12 C13 H13 . . 118.8 ?
    C13 C14 C15 . . 121.41(12) ?
    C13 C14 H14 . . 119.3 ?
    C15 C14 H14 . . 119.3 ?
    C16 C15 C14 . . 118.34(12) ?
    C16 C15 H15 . . 120.8 ?
    C14 C15 H15 . . 120.8 ?
    C15 C16 C17 . . 120.91(12) ?
    C15 C16 H16 . . 119.5 ?
    C17 C16 H16 . . 119.5 ?
    C16 C17 C12 . . 122.25(12) ?
    C16 C17 N2 . . 116.03(11) ?
    C12 C17 N2 . . 121.70(12) ?
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
    C3 Fe C1 C2 . . . . -38.48(9) ?
    C6 Fe C1 C2 . . . . 135.36(9) ?
    C10 Fe C1 C2 . . . . 177.19(8) ?
    C4 Fe C1 C2 . . . . -82.98(10) ?
    C8 Fe C1 C2 . . . . 53.30(14) ?
    C5 Fe C1 C2 . . . . -120.20(12) ?
    C7 Fe C1 C2 . . . . 90.87(9) ?
    C3 Fe C1 C5 . . . . 81.72(9) ?
    C6 Fe C1 C5 . . . . -104.44(9) ?
    C10 Fe C1 C5 . . . . -62.61(11) ?
    C4 Fe C1 C5 . . . . 37.21(9) ?
    C2 Fe C1 C5 . . . . 120.20(12) ?
    C8 Fe C1 C5 . . . . 173.50(9) ?
    C7 Fe C1 C5 . . . . -148.93(8) ?
    C5 C1 C2 C3 . . . . 0.17(15) ?
    Fe C1 C2 C3 . . . . 58.82(9) ?
    C5 C1 C2 Fe . . . . -58.65(9) ?
    C3 Fe C2 C1 . . . . 118.47(12) ?
    C6 Fe C2 C1 . . . . -67.47(11) ?
    C9 Fe C2 C1 . . . . 171.60(9) ?
    C4 Fe C2 C1 . . . . 80.77(9) ?
    C8 Fe C2 C1 . . . . -150.32(9) ?
    C5 Fe C2 C1 . . . . 37.38(9) ?
    C7 Fe C2 C1 . . . . -106.74(9) ?
    C6 Fe C2 C3 . . . . 174.06(8) ?
    C9 Fe C2 C3 . . . . 53.14(13) ?
    C4 Fe C2 C3 . . . . -37.70(8) ?
    C8 Fe C2 C3 . . . . 91.21(9) ?
    C5 Fe C2 C3 . . . . -81.08(9) ?
    C1 Fe C2 C3 . . . . -118.47(12) ?
    C7 Fe C2 C3 . . . . 134.79(8) ?
    C1 C2 C3 C4 . . . . -0.05(15) ?
    Fe C2 C3 C4 . . . . 59.75(9) ?
    C1 C2 C3 Fe . . . . -59.79(9) ?
    C10 Fe C3 C2 . . . . 174.00(8) ?
    C9 Fe C3 C2 . . . . -149.68(8) ?
    C4 Fe C3 C2 . . . . 119.75(11) ?
    C8 Fe C3 C2 . . . . -105.61(9) ?
    C5 Fe C3 C2 . . . . 82.08(9) ?
    C1 Fe C3 C2 . . . . 37.90(8) ?
    C7 Fe C3 C2 . . . . -67.50(10) ?
    C10 Fe C3 C4 . . . . 54.25(12) ?
    C9 Fe C3 C4 . . . . 90.58(8) ?
    C2 Fe C3 C4 . . . . -119.75(11) ?
    C8 Fe C3 C4 . . . . 134.64(8) ?
    C5 Fe C3 C4 . . . . -37.66(8) ?
    C1 Fe C3 C4 . . . . -81.85(9) ?
    C7 Fe C3 C4 . . . . 172.75(7) ?
    C2 C3 C4 C5 . . . . -0.10(15) ?
    Fe C3 C4 C5 . . . . 59.74(9) ?
    C2 C3 C4 Fe . . . . -59.84(9) ?
    C3 Fe C4 C5 . . . . -118.75(12) ?
    C6 Fe C4 C5 . . . . 58.96(13) ?
    C10 Fe C4 C5 . . . . 92.96(9) ?
    C9 Fe C4 C5 . . . . 136.42(8) ?
    C2 Fe C4 C5 . . . . -81.17(9) ?
    C8 Fe C4 C5 . . . . 174.41(8) ?
    C1 Fe C4 C5 . . . . -37.67(9) ?
    C6 Fe C4 C3 . . . . 177.71(8) ?
    C10 Fe C4 C3 . . . . -148.29(8) ?
    C9 Fe C4 C3 . . . . -104.83(8) ?
    C2 Fe C4 C3 . . . . 37.58(8) ?
    C8 Fe C4 C3 . . . . -66.84(11) ?
    C5 Fe C4 C3 . . . . 118.75(12) ?
    C1 Fe C4 C3 . . . . 81.08(9) ?
    C3 C4 C5 C1 . . . . 0.21(15) ?
    Fe C4 C5 C1 . . . . 58.93(9) ?
    C3 C4 C5 Fe . . . . -58.72(9) ?
    C2 C1 C5 C4 . . . . -0.24(15) ?
    Fe C1 C5 C4 . . . . -58.84(9) ?
    C2 C1 C5 Fe . . . . 58.60(9) ?
    C3 Fe C5 C4 . . . . 38.42(9) ?
    C6 Fe C5 C4 . . . . -146.53(9) ?
    C10 Fe C5 C4 . . . . -102.28(9) ?
    C9 Fe C5 C4 . . . . -62.91(11) ?
    C2 Fe C5 C4 . . . . 82.72(9) ?
    C1 Fe C5 C4 . . . . 119.71(12) ?
    C7 Fe C5 C4 . . . . 176.98(10) ?
    C3 Fe C5 C1 . . . . -81.29(9) ?
    C6 Fe C5 C1 . . . . 93.75(9) ?
    C10 Fe C5 C1 . . . . 138.00(8) ?
    C9 Fe C5 C1 . . . . 177.38(8) ?
    C4 Fe C5 C1 . . . . -119.71(12) ?
    C2 Fe C5 C1 . . . . -36.99(9) ?
    C7 Fe C5 C1 . . . . 57.26(13) ?
    C10 Fe C6 C7 . . . . 120.67(10) ?
    C9 Fe C6 C7 . . . . 82.17(8) ?
    C4 Fe C6 C7 . . . . 172.30(8) ?
    C2 Fe C6 C7 . . . . -65.41(10) ?
    C8 Fe C6 C7 . . . . 37.70(8) ?
    C5 Fe C6 C7 . . . . -149.87(8) ?
    C1 Fe C6 C7 . . . . -105.40(8) ?
    C9 Fe C6 C10 . . . . -38.50(7) ?
    C4 Fe C6 C10 . . . . 51.63(12) ?
    C2 Fe C6 C10 . . . . 173.92(7) ?
    C8 Fe C6 C10 . . . . -82.97(8) ?
    C5 Fe C6 C10 . . . . 89.46(8) ?
    C1 Fe C6 C10 . . . . 133.93(8) ?
    C7 Fe C6 C10 . . . . -120.67(10) ?
    C10 C6 C7 C8 . . . . -0.47(14) ?
    Fe C6 C7 C8 . . . . -58.99(9) ?
    C10 C6 C7 Fe . . . . 58.52(9) ?
    C3 Fe C7 C8 . . . . -64.19(11) ?
    C6 Fe C7 C8 . . . . 118.91(11) ?
    C10 Fe C7 C8 . . . . 81.50(8) ?
    C9 Fe C7 C8 . . . . 37.47(8) ?
    C2 Fe C7 C8 . . . . -104.42(9) ?
    C5 Fe C7 C8 . . . . 174.23(9) ?
    C1 Fe C7 C8 . . . . -148.06(8) ?
    C3 Fe C7 C6 . . . . 176.90(8) ?
    C10 Fe C7 C6 . . . . -37.40(7) ?
    C9 Fe C7 C6 . . . . -81.44(8) ?
    C2 Fe C7 C6 . . . . 136.67(8) ?
    C8 Fe C7 C6 . . . . -118.91(11) ?
    C5 Fe C7 C6 . . . . 55.33(13) ?
    C1 Fe C7 C6 . . . . 93.04(8) ?
    C6 C7 C8 C9 . . . . 0.16(14) ?
    Fe C7 C8 C9 . . . . -58.25(9) ?
    C6 C7 C8 Fe . . . . 58.42(8) ?
    C3 Fe C8 C7 . . . . 136.60(9) ?
    C6 Fe C8 C7 . . . . -38.09(8) ?
    C10 Fe C8 C7 . . . . -82.77(8) ?
    C9 Fe C8 C7 . . . . -120.43(11) ?
    C4 Fe C8 C7 . . . . 176.41(8) ?
    C2 Fe C8 C7 . . . . 92.62(9) ?
    C1 Fe C8 C7 . . . . 57.81(13) ?
    C3 Fe C8 C9 . . . . -102.97(9) ?
    C6 Fe C8 C9 . . . . 82.34(8) ?
    C10 Fe C8 C9 . . . . 37.66(8) ?
    C4 Fe C8 C9 . . . . -63.16(11) ?
    C2 Fe C8 C9 . . . . -146.95(8) ?
    C1 Fe C8 C9 . . . . 178.24(9) ?
    C7 Fe C8 C9 . . . . 120.43(11) ?
    C7 C8 C9 C10 . . . . 0.20(14) ?
    Fe C8 C9 C10 . . . . -58.72(8) ?
    C7 C8 C9 Fe . . . . 58.92(9) ?
    C3 Fe C9 C10 . . . . -147.17(8) ?
    C6 Fe C9 C10 . . . . 38.87(8) ?
    C4 Fe C9 C10 . . . . -103.56(8) ?
    C2 Fe C9 C10 . . . . 178.13(9) ?
    C8 Fe C9 C10 . . . . 119.60(11) ?
    C5 Fe C9 C10 . . . . -66.42(10) ?
    C7 Fe C9 C10 . . . . 82.82(8) ?
    C3 Fe C9 C8 . . . . 93.23(9) ?
    C6 Fe C9 C8 . . . . -80.73(8) ?
    C10 Fe C9 C8 . . . . -119.60(11) ?
    C4 Fe C9 C8 . . . . 136.84(8) ?
    C2 Fe C9 C8 . . . . 58.53(13) ?
    C5 Fe C9 C8 . . . . 173.98(8) ?
    C7 Fe C9 C8 . . . . -36.78(8) ?
    C8 C9 C10 C6 . . . . -0.48(13) ?
    Fe C9 C10 C6 . . . . -59.56(8) ?
    C8 C9 C10 C11 . . . . 178.65(11) ?
    Fe C9 C10 C11 . . . . 119.57(12) ?
    C8 C9 C10 Fe . . . . 59.08(9) ?
    C7 C6 C10 C9 . . . . 0.59(14) ?
    Fe C6 C10 C9 . . . . 59.89(8) ?
    C7 C6 C10 C11 . . . . -178.55(11) ?
    Fe C6 C10 C11 . . . . -119.25(12) ?
    C7 C6 C10 Fe . . . . -59.30(9) ?
    C3 Fe C10 C9 . . . . 56.33(12) ?
    C6 Fe C10 C9 . . . . -117.97(11) ?
    C4 Fe C10 C9 . . . . 91.48(8) ?
    C8 Fe C10 C9 . . . . -37.78(8) ?
    C5 Fe C10 C9 . . . . 134.43(8) ?
    C1 Fe C10 C9 . . . . 172.19(8) ?
    C7 Fe C10 C9 . . . . -81.10(8) ?
    C3 Fe C10 C6 . . . . 174.30(8) ?
    C9 Fe C10 C6 . . . . 117.97(11) ?
    C4 Fe C10 C6 . . . . -150.56(7) ?
    C8 Fe C10 C6 . . . . 80.18(8) ?
    C5 Fe C10 C6 . . . . -107.60(8) ?
    C1 Fe C10 C6 . . . . -69.85(10) ?
    C7 Fe C10 C6 . . . . 36.87(7) ?
    C3 Fe C10 C11 . . . . -65.38(14) ?
    C6 Fe C10 C11 . . . . 120.33(14) ?
    C9 Fe C10 C11 . . . . -121.71(14) ?
    C4 Fe C10 C11 . . . . -30.23(12) ?
    C8 Fe C10 C11 . . . . -159.49(12) ?
    C5 Fe C10 C11 . . . . 12.73(12) ?
    C1 Fe C10 C11 . . . . 50.48(14) ?
    C7 Fe C10 C11 . . . . 157.20(12) ?
    C12 N1 C11 C10 . . . . -79.74(16) ?
    C9 C10 C11 N1 . . . . 89.84(16) ?
    C6 C10 C11 N1 . . . . -91.19(15) ?
    Fe C10 C11 N1 . . . . 180.00(9) ?
    C11 N1 C12 C13 . . . . -11.7(2) ?
    C11 N1 C12 C17 . . . . 168.50(13) ?
    N1 C12 C13 C14 . . . . -177.79(13) ?
    C17 C12 C13 C14 . . . . 1.99(19) ?
    C12 C13 C14 C15 . . . . -1.9(2) ?
    C13 C14 C15 C16 . . . . 0.0(2) ?
    C14 C15 C16 C17 . . . . 1.7(2) ?
    C15 C16 C17 C12 . . . . -1.6(2) ?
    C15 C16 C17 N2 . . . . 176.83(13) ?
    N1 C12 C17 C16 . . . . 179.49(13) ?
    C13 C12 C17 C16 . . . . -0.3(2) ?
    N1 C12 C17 N2 . . . . 1.2(2) ?
    C13 C12 C17 N2 . . . . -178.58(12) ?
    O1 N2 C17 C16 . . . . 9.75(19) ?
    O2 N2 C17 C16 . . . . -169.57(13) ?
    O1 N2 C17 C12 . . . . -171.86(13) ?
    O2 N2 C17 C12 . . . . 8.8(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H10 O2 . 0.827(16) 2.01(2) 2.6511(19) 133.3(18) yes
    N1 H10 N2 . 0.827(16) 2.624(19) 2.961(2) 106.0(16) yes
    C4 H4 O2 1_565 0.93 2.5700 3.283(2) 134.00 yes
    C16 H16 O1 . 0.93 2.3600 2.683(2) 100.00 ?
