##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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     2008-01-11
_journal_date_accepted     2008-02-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     m514
_journal_page_last     m515
_journal_paper_category     QM
_journal_coeditor_code     HY2116
_publ_contact_author_name     'Turgut Cin, G\"unseli'
_publ_contact_author_address
;
Department of Chemistry
Faculty of Arts and Sciences
Akdeniz University
TR-07058
Antalya
Turkey
;
_publ_contact_author_email     gturgut@akdeniz.edu.tr
_publ_section_title
;
1-Acetyl-3-ferrocenyl-5-(2-nitrophenyl)-2-pyrazoline
;
loop_
    _publ_author_name
    _publ_author_address
    'Turgut Cin, G\"unseli'
;
Department of Chemistry
Faculty of Arts and Sciences
Akdeniz University
TR-07058 Antalya
Turkey
;
    'Demirel, Seda'
;
Department of Chemistry
Faculty of Arts and Sciences
Akdeniz University
TR-07058 Antalya
Turkey
;
    'Karaday\?i, Nevzat'
;
Samsun Vocational School
Ondokuz May\?is University
TR-55139 Samsun
Turkey
;
    'B\"uy\"ukg\"ung\"or, Orhan'
;
Department of Physics
Faculty of Arts and Sciences
Ondokuz May\?is University
TR-55139 Samsun
Turkey
;
data_I
_chemical_name_systematic
;
1-Acetyl-3-ferrocenyl-5-(2-nitrophenyl)-2-pyrazoline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H19 Fe N3 O3'
_chemical_formula_sum     'C21 H19 Fe N3 O3'
_chemical_formula_iupac     '[Fe (C5 H5) (C16 H14 N3 O3)]'
_chemical_formula_weight     417.24
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.6691(6)
_cell_length_b     13.4779(7)
_cell_length_c     31.4930(15)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3679.7(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     16565
_cell_measurement_theta_min     1.64
_cell_measurement_theta_max     27.94
_cell_measurement_temperature     296
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'red'
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.506
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1728
_exptl_absorpt_coefficient_mu     0.848
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(X-RED32; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.6362
_exptl_absorpt_correction_T_max     0.8615
_diffrn_ambient_temperature     296(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     'Stoe IPDSII'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     17799
_diffrn_reflns_av_R_equivalents     0.0610
_diffrn_reflns_av_sigmaI/netI     0.0418
_diffrn_reflns_theta_min     2.59
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -38
_diffrn_reflns_limit_l_max     38
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3613
_reflns_number_gt     2409
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0679
_refine_ls_R_factor_gt     0.0371
_refine_ls_wR_factor_gt     0.0769
_refine_ls_wR_factor_ref     0.0860
_refine_ls_goodness_of_fit_ref     0.938
_refine_ls_restrained_S_all     0.938
_refine_ls_number_reflns     3613
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[\s^2^(Fo^2^)+(0.0440P)^2^] where P=(Fo^2^+2Fc^2^)/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     0.192
_refine_diff_density_min     -0.288
_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'
    'O' 'O' 0.0106 0.0060
                         '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     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2003)
;
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_disorder_assembly
    _atom_site_disorder_group
    C C1 0.4226(3) 0.55162(19) 0.68996(7) 0.0419(6) Uani d . 1 . .
    C C2 0.3958(3) 0.5738(2) 0.73262(8) 0.0481(7) Uani d . 1 . .
    C C3 0.4637(4) 0.5207(2) 0.76547(9) 0.0617(8) Uani d . 1 . .
    H H3 0.4434 0.5376 0.7935 0.074 Uiso calc R 1 . .
    C C4 0.5601(4) 0.4437(2) 0.75645(9) 0.0674(9) Uani d . 1 . .
    H H4 0.6058 0.4078 0.7783 0.081 Uiso calc R 1 . .
    C C5 0.5895(4) 0.4195(2) 0.71485(10) 0.0636(8) Uani d . 1 . .
    H H5 0.6561 0.3675 0.7085 0.076 Uiso calc R 1 . .
    C C6 0.5201(3) 0.4723(2) 0.68231(9) 0.0518(7) Uani d . 1 . .
    H H6 0.5398 0.4539 0.6544 0.062 Uiso calc R 1 . .
    C C7 0.3550(3) 0.61147(18) 0.65354(7) 0.0413(6) Uani d . 1 . .
    H H7 0.2483 0.6299 0.6601 0.050 Uiso calc R 1 . .
    C C8 0.4494(3) 0.70502(18) 0.64348(7) 0.0434(6) Uani d . 1 . .
    H H8A 0.3860 0.7642 0.6452 0.052 Uiso calc R 1 . .
    H H8B 0.5363 0.7118 0.6627 0.052 Uiso calc R 1 . .
    C C9 0.5024(3) 0.68659(19) 0.59887(8) 0.0409(6) Uani d . 1 . .
    C C10 0.2617(3) 0.48364(19) 0.60260(8) 0.0461(6) Uani d . 1 . .
    C C11 0.2627(4) 0.4488(2) 0.55716(9) 0.0591(8) Uani d . 1 . .
    H H11A 0.3349 0.4877 0.5411 0.089 Uiso calc PR 0.50 . .
    H H11B 0.1614 0.4562 0.5453 0.089 Uiso calc PR 0.50 . .
    H H11C 0.2925 0.3802 0.5562 0.089 Uiso calc PR 0.50 . .
    H H11D 0.1910 0.3950 0.5539 0.089 Uiso calc PR 0.50 . .
    H H11E 0.3644 0.4265 0.5498 0.089 Uiso calc PR 0.50 . .
    H H11F 0.2334 0.5025 0.5389 0.089 Uiso calc PR 0.50 . .
    C C12 0.6069(3) 0.7528(2) 0.57636(8) 0.0456(6) Uani d . 1 . .
    C C13 0.6708(3) 0.84249(19) 0.59343(9) 0.0523(7) Uani d . 1 . .
    H H13 0.6467 0.8705 0.6196 0.063 Uiso calc R 1 . .
    C C14 0.7769(4) 0.8809(2) 0.56346(10) 0.0593(8) Uani d . 1 . .
    H H14 0.8346 0.9387 0.5665 0.071 Uiso calc R 1 . .
    C C15 0.7799(4) 0.8165(3) 0.52835(9) 0.0615(8) Uani d . 1 . .
    H H15 0.8397 0.8247 0.5041 0.074 Uiso calc R 1 . .
    C C16 0.6772(3) 0.7373(2) 0.53603(8) 0.0558(7) Uani d . 1 . .
    H H16 0.6586 0.6841 0.5179 0.067 Uiso calc R 1 . .
    C C17 1.0530(4) 0.7425(2) 0.60978(10) 0.0635(8) Uani d . 1 . .
    H H17 1.1130 0.7984 0.6149 0.076 Uiso calc R 1 . .
    C C18 1.0552(4) 0.6843(3) 0.57284(10) 0.0665(9) Uani d . 1 . .
    H H18 1.1166 0.6948 0.5491 0.080 Uiso calc R 1 . .
    C C19 0.9461(4) 0.6060(2) 0.57837(10) 0.0628(8) Uani d . 1 . .
    H H19 0.9238 0.5560 0.5590 0.075 Uiso calc R 1 . .
    C C20 0.8795(4) 0.6185(2) 0.61815(9) 0.0560(8) Uani d . 1 . .
    H H20 0.8039 0.5782 0.6300 0.067 Uiso calc R 1 . .
    C C21 0.9452(4) 0.7019(2) 0.63740(9) 0.0581(8) Uani d . 1 . .
    H H21 0.9208 0.7262 0.6642 0.070 Uiso calc R 1 . .
    N N1 0.2950(3) 0.6566(2) 0.74518(7) 0.0580(7) Uani d . 1 . .
    N N2 0.3604(3) 0.55775(15) 0.61266(6) 0.0421(5) Uani d . 1 . .
    N N3 0.4499(2) 0.60674(15) 0.58194(6) 0.0446(5) Uani d . 1 . .
    O O1 0.2640(4) 0.72062(19) 0.71980(7) 0.0857(8) Uani d . 1 . .
    O O2 0.2464(3) 0.6580(2) 0.78155(7) 0.0818(7) Uani d . 1 . .
    O O3 0.1803(2) 0.44698(15) 0.63000(6) 0.0583(5) Uani d . 1 . .
    Fe Fe1 0.84006(4) 0.74057(2) 0.581679(10) 0.04091(12) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0399(16) 0.0440(15) 0.0416(13) -0.0072(12) -0.0011(11) 0.0002(10)
    C2 0.0490(17) 0.0539(16) 0.0413(13) -0.0120(13) 0.0013(12) -0.0019(12)
    C3 0.074(2) 0.068(2) 0.0428(14) -0.0177(18) -0.0069(15) 0.0037(14)
    C4 0.082(3) 0.062(2) 0.0585(19) -0.0102(18) -0.0196(17) 0.0154(15)
    C5 0.066(2) 0.0507(17) 0.074(2) 0.0045(15) -0.0186(17) 0.0042(14)
    C6 0.0549(19) 0.0486(16) 0.0519(14) 0.0029(13) -0.0086(13) -0.0040(12)
    C7 0.0393(15) 0.0431(13) 0.0415(12) 0.0030(12) 0.0012(11) -0.0015(10)
    C8 0.0465(17) 0.0377(14) 0.0459(13) -0.0015(11) -0.0004(12) -0.0004(10)
    C9 0.0366(15) 0.0453(14) 0.0410(12) 0.0036(12) 0.0000(11) 0.0027(11)
    C10 0.0453(17) 0.0407(15) 0.0523(14) 0.0038(12) -0.0092(14) -0.0006(12)
    C11 0.065(2) 0.0535(17) 0.0591(17) -0.0014(15) -0.0124(15) -0.0099(14)
    C12 0.0397(13) 0.0507(15) 0.0463(13) 0.0012(12) -0.0023(10) 0.0069(12)
    C13 0.0491(17) 0.0425(14) 0.0654(17) 0.0040(13) 0.0066(14) 0.0035(12)
    C14 0.0485(18) 0.0491(17) 0.080(2) 0.0027(14) 0.0036(16) 0.0182(15)
    C15 0.0476(18) 0.081(2) 0.0553(16) -0.0004(16) 0.0005(14) 0.0281(16)
    C16 0.0494(17) 0.0726(19) 0.0453(13) -0.0041(15) -0.0064(12) 0.0084(13)
    C17 0.0484(18) 0.0617(19) 0.080(2) -0.0082(16) -0.0178(15) 0.0164(17)
    C18 0.051(2) 0.077(2) 0.072(2) 0.0194(16) 0.0159(15) 0.0255(17)
    C19 0.066(2) 0.0487(17) 0.0741(19) 0.0129(14) 0.0016(18) -0.0015(15)
    C20 0.0488(19) 0.0531(17) 0.0661(18) 0.0028(13) 0.0005(14) 0.0162(14)
    C21 0.063(2) 0.0604(19) 0.0511(15) 0.0017(15) -0.0096(15) 0.0077(13)
    N1 0.0575(17) 0.0695(17) 0.0470(13) -0.0097(13) 0.0061(12) -0.0141(12)
    N2 0.0446(14) 0.0448(12) 0.0370(10) -0.0040(10) -0.0023(9) -0.0012(8)
    N3 0.0421(13) 0.0491(12) 0.0427(10) -0.0009(10) -0.0021(11) 0.0011(10)
    O1 0.118(2) 0.0697(16) 0.0695(14) 0.0264(15) 0.0219(14) -0.0057(12)
    O2 0.0805(18) 0.114(2) 0.0514(12) -0.0059(15) 0.0203(12) -0.0183(12)
    O3 0.0565(14) 0.0540(12) 0.0644(12) -0.0097(10) -0.0030(10) 0.0044(9)
    Fe1 0.0390(2) 0.0419(2) 0.04183(17) 0.00169(17) 0.00009(16) 0.00513(16)
_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
    C1 C6 . 1.384(4) ?
    C1 C2 . 1.396(3) ?
    C1 C7 . 1.519(3) ?
    C2 C3 . 1.389(4) ?
    C2 N1 . 1.472(4) ?
    C3 C4 . 1.362(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.374(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.385(4) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 N2 . 1.478(3) ?
    C7 C8 . 1.536(3) ?
    C7 H7 . 0.9800 ?
    C8 C9 . 1.499(3) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 N3 . 1.284(3) ?
    C9 C12 . 1.456(4) ?
    C10 O3 . 1.219(3) ?
    C10 N2 . 1.353(3) ?
    C10 C11 . 1.506(4) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C11 H11D . 0.9600 ?
    C11 H11E . 0.9600 ?
    C11 H11F . 0.9600 ?
    C12 C16 . 1.424(4) ?
    C12 C13 . 1.434(4) ?
    C12 Fe1 . 2.035(3) y
    C13 C14 . 1.416(4) ?
    C13 Fe1 . 2.044(3) y
    C13 H13 . 0.9300 ?
    C14 C15 . 1.407(4) ?
    C14 Fe1 . 2.051(3) y
    C14 H14 . 0.9300 ?
    C15 C16 . 1.411(4) ?
    C15 Fe1 . 2.034(3) y
    C15 H15 . 0.9300 ?
    C16 Fe1 . 2.016(3) y
    C16 H16 . 0.9300 ?
    C17 C21 . 1.389(4) ?
    C17 C18 . 1.403(5) ?
    C17 Fe1 . 2.047(3) y
    C17 H17 . 0.9300 ?
    C18 C19 . 1.428(5) ?
    C18 Fe1 . 2.033(3) y
    C18 H18 . 0.9300 ?
    C19 C20 . 1.390(4) ?
    C19 Fe1 . 2.036(3) y
    C19 H19 . 0.9300 ?
    C20 C21 . 1.398(4) ?
    C20 Fe1 . 2.035(3) y
    C20 H20 . 0.9300 ?
    C21 Fe1 . 2.045(3) y
    C21 H21 . 0.9300 ?
    N1 O1 . 1.206(3) ?
    N1 O2 . 1.221(3) ?
    N2 N3 . 1.405(3) ?
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
    C6 C1 C2 . . 115.7(2) ?
    C6 C1 C7 . . 120.9(2) ?
    C2 C1 C7 . . 123.3(2) ?
    C3 C2 C1 . . 122.4(3) ?
    C3 C2 N1 . . 116.3(3) ?
    C1 C2 N1 . . 121.3(2) ?
    C4 C3 C2 . . 119.8(3) ?
    C4 C3 H3 . . 120.1 ?
    C2 C3 H3 . . 120.1 ?
    C3 C4 C5 . . 119.6(3) ?
    C3 C4 H4 . . 120.2 ?
    C5 C4 H4 . . 120.2 ?
    C4 C5 C6 . . 120.2(3) ?
    C4 C5 H5 . . 119.9 ?
    C6 C5 H5 . . 119.9 ?
    C1 C6 C5 . . 122.2(3) ?
    C1 C6 H6 . . 118.9 ?
    C5 C6 H6 . . 118.9 ?
    N2 C7 C1 . . 112.7(2) ?
    N2 C7 C8 . . 101.87(19) ?
    C1 C7 C8 . . 112.7(2) ?
    N2 C7 H7 . . 109.8 ?
    C1 C7 H7 . . 109.8 ?
    C8 C7 H7 . . 109.8 ?
    C9 C8 C7 . . 102.7(2) ?
    C9 C8 H8A . . 111.2 ?
    C7 C8 H8A . . 111.2 ?
    C9 C8 H8B . . 111.2 ?
    C7 C8 H8B . . 111.2 ?
    H8A C8 H8B . . 109.1 ?
    N3 C9 C12 . . 122.1(2) ?
    N3 C9 C8 . . 114.8(2) ?
    C12 C9 C8 . . 123.1(2) ?
    O3 C10 N2 . . 120.0(2) ?
    O3 C10 C11 . . 123.3(3) ?
    N2 C10 C11 . . 116.7(3) ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C10 C11 H11D . . 109.5 ?
    H11A C11 H11D . . 141.1 ?
    H11B C11 H11D . . 56.3 ?
    H11C C11 H11D . . 56.3 ?
    C10 C11 H11E . . 109.5 ?
    H11A C11 H11E . . 56.3 ?
    H11B C11 H11E . . 141.1 ?
    H11C C11 H11E . . 56.3 ?
    H11D C11 H11E . . 109.5 ?
    C10 C11 H11F . . 109.5 ?
    H11A C11 H11F . . 56.3 ?
    H11B C11 H11F . . 56.3 ?
    H11C C11 H11F . . 141.1 ?
    H11D C11 H11F . . 109.5 ?
    H11E C11 H11F . . 109.5 ?
    C16 C12 C13 . . 107.0(2) ?
    C16 C12 C9 . . 127.6(3) ?
    C13 C12 C9 . . 125.1(2) ?
    C16 C12 Fe1 . . 68.67(15) ?
    C13 C12 Fe1 . . 69.73(16) ?
    C9 C12 Fe1 . . 121.89(18) ?
    C14 C13 C12 . . 108.0(3) ?
    C14 C13 Fe1 . . 70.04(17) ?
    C12 C13 Fe1 . . 69.09(15) ?
    C14 C13 H13 . . 126.0 ?
    C12 C13 H13 . . 126.0 ?
    Fe1 C13 H13 . . 126.5 ?
    C15 C14 C13 . . 108.1(3) ?
    C15 C14 Fe1 . . 69.23(17) ?
    C13 C14 Fe1 . . 69.50(16) ?
    C15 C14 H14 . . 126.0 ?
    C13 C14 H14 . . 126.0 ?
    Fe1 C14 H14 . . 126.9 ?
    C14 C15 C16 . . 108.7(3) ?
    C14 C15 Fe1 . . 70.50(16) ?
    C16 C15 Fe1 . . 68.89(15) ?
    C14 C15 H15 . . 125.6 ?
    C16 C15 H15 . . 125.6 ?
    Fe1 C15 H15 . . 126.5 ?
    C15 C16 C12 . . 108.2(3) ?
    C15 C16 Fe1 . . 70.33(16) ?
    C12 C16 Fe1 . . 70.16(15) ?
    C15 C16 H16 . . 125.9 ?
    C12 C16 H16 . . 125.9 ?
    Fe1 C16 H16 . . 125.2 ?
    C21 C17 C18 . . 108.0(3) ?
    C21 C17 Fe1 . . 70.08(17) ?
    C18 C17 Fe1 . . 69.33(18) ?
    C21 C17 H17 . . 126.0 ?
    C18 C17 H17 . . 126.0 ?
    Fe1 C17 H17 . . 126.1 ?
    C17 C18 C19 . . 107.6(3) ?
    C17 C18 Fe1 . . 70.44(18) ?
    C19 C18 Fe1 . . 69.60(18) ?
    C17 C18 H18 . . 126.2 ?
    C19 C18 H18 . . 126.2 ?
    Fe1 C18 H18 . . 125.4 ?
    C20 C19 C18 . . 107.2(3) ?
    C20 C19 Fe1 . . 70.00(17) ?
    C18 C19 Fe1 . . 69.32(17) ?
    C20 C19 H19 . . 126.4 ?
    C18 C19 H19 . . 126.4 ?
    Fe1 C19 H19 . . 125.8 ?
    C19 C20 C21 . . 108.6(3) ?
    C19 C20 Fe1 . . 70.08(16) ?
    C21 C20 Fe1 . . 70.33(16) ?
    C19 C20 H20 . . 125.7 ?
    C21 C20 H20 . . 125.7 ?
    Fe1 C20 H20 . . 125.5 ?
    C17 C21 C20 . . 108.6(3) ?
    C17 C21 Fe1 . . 70.24(16) ?
    C20 C21 Fe1 . . 69.58(16) ?
    C17 C21 H21 . . 125.7 ?
    C20 C21 H21 . . 125.7 ?
    Fe1 C21 H21 . . 126.1 ?
    O1 N1 O2 . . 122.3(3) ?
    O1 N1 C2 . . 119.8(2) ?
    O2 N1 C2 . . 117.9(3) ?
    C10 N2 N3 . . 122.3(2) ?
    C10 N2 C7 . . 123.1(2) ?
    N3 N2 C7 . . 112.77(19) ?
    C9 N3 N2 . . 107.67(19) ?
    C16 Fe1 C18 . . 122.47(13) ?
    C16 Fe1 C15 . . 40.78(12) ?
    C18 Fe1 C15 . . 108.04(13) ?
    C16 Fe1 C12 . . 41.17(11) ?
    C18 Fe1 C12 . . 158.50(14) ?
    C15 Fe1 C12 . . 68.71(11) ?
    C16 Fe1 C20 . . 120.16(13) ?
    C18 Fe1 C20 . . 67.76(12) ?
    C15 Fe1 C20 . . 156.25(14) ?
    C12 Fe1 C20 . . 106.19(11) ?
    C16 Fe1 C19 . . 105.08(13) ?
    C18 Fe1 C19 . . 41.08(13) ?
    C15 Fe1 C19 . . 121.42(14) ?
    C12 Fe1 C19 . . 121.10(13) ?
    C20 Fe1 C19 . . 39.92(12) ?
    C16 Fe1 C13 . . 68.97(12) ?
    C18 Fe1 C13 . . 159.13(14) ?
    C15 Fe1 C13 . . 68.14(12) ?
    C12 Fe1 C13 . . 41.18(11) ?
    C20 Fe1 C13 . . 124.17(12) ?
    C19 Fe1 C13 . . 158.78(13) ?
    C16 Fe1 C21 . . 156.74(12) ?
    C18 Fe1 C21 . . 67.26(13) ?
    C15 Fe1 C21 . . 161.94(14) ?
    C12 Fe1 C21 . . 122.28(12) ?
    C20 Fe1 C21 . . 40.08(12) ?
    C19 Fe1 C21 . . 67.40(13) ?
    C13 Fe1 C21 . . 109.62(12) ?
    C16 Fe1 C17 . . 160.09(13) ?
    C18 Fe1 C17 . . 40.24(13) ?
    C15 Fe1 C17 . . 125.55(13) ?
    C12 Fe1 C17 . . 158.46(12) ?
    C20 Fe1 C17 . . 67.35(12) ?
    C19 Fe1 C17 . . 68.06(14) ?
    C13 Fe1 C17 . . 124.09(13) ?
    C21 Fe1 C17 . . 39.68(12) ?
    C16 Fe1 C14 . . 68.53(13) ?
    C18 Fe1 C14 . . 123.41(13) ?
    C15 Fe1 C14 . . 40.27(13) ?
    C12 Fe1 C14 . . 68.73(12) ?
    C20 Fe1 C14 . . 161.46(12) ?
    C19 Fe1 C14 . . 158.08(13) ?
    C13 Fe1 C14 . . 40.47(11) ?
    C21 Fe1 C14 . . 126.43(13) ?
    C17 Fe1 C14 . . 110.47(13) ?
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
    C6 C1 C2 C3 . . . . 0.7(4) ?
    C7 C1 C2 C3 . . . . -177.3(3) ?
    C6 C1 C2 N1 . . . . 179.6(3) ?
    C7 C1 C2 N1 . . . . 1.7(4) ?
    C1 C2 C3 C4 . . . . -0.1(5) ?
    N1 C2 C3 C4 . . . . -179.1(3) ?
    C2 C3 C4 C5 . . . . 0.1(5) ?
    C3 C4 C5 C6 . . . . -0.7(5) ?
    C2 C1 C6 C5 . . . . -1.3(4) ?
    C7 C1 C6 C5 . . . . 176.7(3) ?
    C4 C5 C6 C1 . . . . 1.3(5) ?
    C6 C1 C7 N2 . . . . 19.3(3) ?
    C2 C1 C7 N2 . . . . -162.9(2) ?
    C6 C1 C7 C8 . . . . -95.4(3) ?
    C2 C1 C7 C8 . . . . 82.5(3) ?
    N2 C7 C8 C9 . . . . -3.4(3) ?
    C1 C7 C8 C9 . . . . 117.6(2) ?
    C7 C8 C9 N3 . . . . 3.9(3) ?
    C7 C8 C9 C12 . . . . -175.3(2) ?
    N3 C9 C12 C16 . . . . -6.5(4) ?
    C8 C9 C12 C16 . . . . 172.7(3) ?
    N3 C9 C12 C13 . . . . -179.4(3) ?
    C8 C9 C12 C13 . . . . -0.3(4) ?
    N3 C9 C12 Fe1 . . . . -93.0(3) ?
    C8 C9 C12 Fe1 . . . . 86.2(3) ?
    C16 C12 C13 C14 . . . . 0.7(3) ?
    C9 C12 C13 C14 . . . . 174.8(3) ?
    Fe1 C12 C13 C14 . . . . 59.4(2) ?
    C16 C12 C13 Fe1 . . . . -58.77(19) ?
    C9 C12 C13 Fe1 . . . . 115.4(3) ?
    C12 C13 C14 C15 . . . . -0.2(3) ?
    Fe1 C13 C14 C15 . . . . 58.6(2) ?
    C12 C13 C14 Fe1 . . . . -58.83(19) ?
    C13 C14 C15 C16 . . . . -0.4(3) ?
    Fe1 C14 C15 C16 . . . . 58.4(2) ?
    C13 C14 C15 Fe1 . . . . -58.8(2) ?
    C14 C15 C16 C12 . . . . 0.8(3) ?
    Fe1 C15 C16 C12 . . . . 60.21(19) ?
    C14 C15 C16 Fe1 . . . . -59.4(2) ?
    C13 C12 C16 C15 . . . . -0.9(3) ?
    C9 C12 C16 C15 . . . . -174.8(3) ?
    Fe1 C12 C16 C15 . . . . -60.3(2) ?
    C13 C12 C16 Fe1 . . . . 59.44(19) ?
    C9 C12 C16 Fe1 . . . . -114.5(3) ?
    C21 C17 C18 C19 . . . . -0.3(4) ?
    Fe1 C17 C18 C19 . . . . -59.9(2) ?
    C21 C17 C18 Fe1 . . . . 59.7(2) ?
    C17 C18 C19 C20 . . . . 0.4(3) ?
    Fe1 C18 C19 C20 . . . . -60.0(2) ?
    C17 C18 C19 Fe1 . . . . 60.4(2) ?
    C18 C19 C20 C21 . . . . -0.4(3) ?
    Fe1 C19 C20 C21 . . . . -60.0(2) ?
    C18 C19 C20 Fe1 . . . . 59.6(2) ?
    C18 C17 C21 C20 . . . . 0.0(4) ?
    Fe1 C17 C21 C20 . . . . 59.2(2) ?
    C18 C17 C21 Fe1 . . . . -59.2(2) ?
    C19 C20 C21 C17 . . . . 0.2(3) ?
    Fe1 C20 C21 C17 . . . . -59.6(2) ?
    C19 C20 C21 Fe1 . . . . 59.9(2) ?
    C3 C2 N1 O1 . . . . 161.2(3) ?
    C1 C2 N1 O1 . . . . -17.8(4) ?
    C3 C2 N1 O2 . . . . -18.3(4) ?
    C1 C2 N1 O2 . . . . 162.7(3) ?
    O3 C10 N2 N3 . . . . -176.0(2) ?
    C11 C10 N2 N3 . . . . 5.6(4) ?
    O3 C10 N2 C7 . . . . -12.4(4) ?
    C11 C10 N2 C7 . . . . 169.3(2) ?
    C1 C7 N2 C10 . . . . 76.4(3) ?
    C8 C7 N2 C10 . . . . -162.6(2) ?
    C1 C7 N2 N3 . . . . -118.6(2) ?
    C8 C7 N2 N3 . . . . 2.4(3) ?
    C12 C9 N3 N2 . . . . 176.7(2) ?
    C8 C9 N3 N2 . . . . -2.5(3) ?
    C10 N2 N3 C9 . . . . 165.0(2) ?
    C7 N2 N3 C9 . . . . -0.1(3) ?
    C15 C16 Fe1 C18 . . . . -79.9(2) ?
    C12 C16 Fe1 C18 . . . . 161.37(17) ?
    C12 C16 Fe1 C15 . . . . -118.8(3) ?
    C15 C16 Fe1 C12 . . . . 118.8(3) ?
    C15 C16 Fe1 C20 . . . . -161.29(19) ?
    C12 C16 Fe1 C20 . . . . 80.0(2) ?
    C15 C16 Fe1 C19 . . . . -120.9(2) ?
    C12 C16 Fe1 C19 . . . . 120.30(18) ?
    C15 C16 Fe1 C13 . . . . 80.5(2) ?
    C12 C16 Fe1 C13 . . . . -38.25(16) ?
    C15 C16 Fe1 C21 . . . . 171.5(3) ?
    C12 C16 Fe1 C21 . . . . 52.7(4) ?
    C15 C16 Fe1 C17 . . . . -54.1(5) ?
    C12 C16 Fe1 C17 . . . . -172.8(3) ?
    C15 C16 Fe1 C14 . . . . 36.94(19) ?
    C12 C16 Fe1 C14 . . . . -81.82(18) ?
    C17 C18 Fe1 C16 . . . . 166.73(17) ?
    C19 C18 Fe1 C16 . . . . -74.9(2) ?
    C17 C18 Fe1 C15 . . . . 124.18(19) ?
    C19 C18 Fe1 C15 . . . . -117.4(2) ?
    C17 C18 Fe1 C12 . . . . -158.3(3) ?
    C19 C18 Fe1 C12 . . . . -39.9(4) ?
    C17 C18 Fe1 C20 . . . . -80.74(19) ?
    C19 C18 Fe1 C20 . . . . 37.64(18) ?
    C17 C18 Fe1 C19 . . . . -118.4(3) ?
    C17 C18 Fe1 C13 . . . . 48.4(4) ?
    C19 C18 Fe1 C13 . . . . 166.8(3) ?
    C17 C18 Fe1 C21 . . . . -37.20(18) ?
    C19 C18 Fe1 C21 . . . . 81.2(2) ?
    C19 C18 Fe1 C17 . . . . 118.4(3) ?
    C17 C18 Fe1 C14 . . . . 82.5(2) ?
    C19 C18 Fe1 C14 . . . . -159.15(19) ?
    C14 C15 Fe1 C16 . . . . 120.1(3) ?
    C14 C15 Fe1 C18 . . . . -120.8(2) ?
    C16 C15 Fe1 C18 . . . . 119.1(2) ?
    C14 C15 Fe1 C12 . . . . 81.82(19) ?
    C16 C15 Fe1 C12 . . . . -38.28(18) ?
    C14 C15 Fe1 C20 . . . . 163.6(3) ?
    C16 C15 Fe1 C20 . . . . 43.5(4) ?
    C14 C15 Fe1 C19 . . . . -163.88(18) ?
    C16 C15 Fe1 C19 . . . . 76.0(2) ?
    C14 C15 Fe1 C13 . . . . 37.39(18) ?
    C16 C15 Fe1 C13 . . . . -82.7(2) ?
    C14 C15 Fe1 C21 . . . . -49.0(5) ?
    C16 C15 Fe1 C21 . . . . -169.1(4) ?
    C14 C15 Fe1 C17 . . . . -79.7(2) ?
    C16 C15 Fe1 C17 . . . . 160.19(19) ?
    C16 C15 Fe1 C14 . . . . -120.1(3) ?
    C13 C12 Fe1 C16 . . . . -118.6(2) ?
    C9 C12 Fe1 C16 . . . . 121.9(3) ?
    C16 C12 Fe1 C18 . . . . -47.3(4) ?
    C13 C12 Fe1 C18 . . . . -166.0(3) ?
    C9 C12 Fe1 C18 . . . . 74.6(4) ?
    C16 C12 Fe1 C15 . . . . 37.92(18) ?
    C13 C12 Fe1 C15 . . . . -80.71(18) ?
    C9 C12 Fe1 C15 . . . . 159.9(3) ?
    C16 C12 Fe1 C20 . . . . -117.56(18) ?
    C13 C12 Fe1 C20 . . . . 123.81(17) ?
    C9 C12 Fe1 C20 . . . . 4.4(2) ?
    C16 C12 Fe1 C19 . . . . -76.8(2) ?
    C13 C12 Fe1 C19 . . . . 164.57(17) ?
    C9 C12 Fe1 C19 . . . . 45.1(3) ?
    C16 C12 Fe1 C13 . . . . 118.6(2) ?
    C9 C12 Fe1 C13 . . . . -119.4(3) ?
    C16 C12 Fe1 C21 . . . . -158.19(18) ?
    C13 C12 Fe1 C21 . . . . 83.18(18) ?
    C9 C12 Fe1 C21 . . . . -36.3(3) ?
    C16 C12 Fe1 C17 . . . . 173.3(3) ?
    C13 C12 Fe1 C17 . . . . 54.7(4) ?
    C9 C12 Fe1 C17 . . . . -64.7(4) ?
    C16 C12 Fe1 C14 . . . . 81.28(19) ?
    C13 C12 Fe1 C14 . . . . -37.35(16) ?
    C9 C12 Fe1 C14 . . . . -156.8(2) ?
    C19 C20 Fe1 C16 . . . . 77.0(2) ?
    C21 C20 Fe1 C16 . . . . -163.69(18) ?
    C19 C20 Fe1 C18 . . . . -38.7(2) ?
    C21 C20 Fe1 C18 . . . . 80.6(2) ?
    C19 C20 Fe1 C15 . . . . 45.6(4) ?
    C21 C20 Fe1 C15 . . . . 165.0(3) ?
    C19 C20 Fe1 C12 . . . . 119.41(19) ?
    C21 C20 Fe1 C12 . . . . -121.23(19) ?
    C21 C20 Fe1 C19 . . . . 119.4(3) ?
    C19 C20 Fe1 C13 . . . . 160.80(19) ?
    C21 C20 Fe1 C13 . . . . -79.8(2) ?
    C19 C20 Fe1 C21 . . . . -119.4(3) ?
    C19 C20 Fe1 C17 . . . . -82.4(2) ?
    C21 C20 Fe1 C17 . . . . 36.95(19) ?
    C19 C20 Fe1 C14 . . . . -169.4(4) ?
    C21 C20 Fe1 C14 . . . . -50.0(5) ?
    C20 C19 Fe1 C16 . . . . -119.27(19) ?
    C18 C19 Fe1 C16 . . . . 122.48(19) ?
    C20 C19 Fe1 C18 . . . . 118.2(3) ?
    C20 C19 Fe1 C15 . . . . -160.29(19) ?
    C18 C19 Fe1 C15 . . . . 81.5(2) ?
    C20 C19 Fe1 C12 . . . . -77.7(2) ?
    C18 C19 Fe1 C12 . . . . 164.07(18) ?
    C18 C19 Fe1 C20 . . . . -118.2(3) ?
    C20 C19 Fe1 C13 . . . . -48.7(4) ?
    C18 C19 Fe1 C13 . . . . -167.0(3) ?
    C20 C19 Fe1 C21 . . . . 37.44(19) ?
    C18 C19 Fe1 C21 . . . . -80.8(2) ?
    C20 C19 Fe1 C17 . . . . 80.5(2) ?
    C18 C19 Fe1 C17 . . . . -37.78(19) ?
    C20 C19 Fe1 C14 . . . . 171.0(3) ?
    C18 C19 Fe1 C14 . . . . 52.7(4) ?
    C14 C13 Fe1 C16 . . . . -81.2(2) ?
    C12 C13 Fe1 C16 . . . . 38.25(15) ?
    C14 C13 Fe1 C18 . . . . 46.1(4) ?
    C12 C13 Fe1 C18 . . . . 165.5(3) ?
    C14 C13 Fe1 C15 . . . . -37.22(19) ?
    C12 C13 Fe1 C15 . . . . 82.21(17) ?
    C14 C13 Fe1 C12 . . . . -119.4(2) ?
    C14 C13 Fe1 C20 . . . . 165.90(19) ?
    C12 C13 Fe1 C20 . . . . -74.68(19) ?
    C14 C13 Fe1 C19 . . . . -158.4(3) ?
    C12 C13 Fe1 C19 . . . . -39.0(4) ?
    C14 C13 Fe1 C21 . . . . 123.6(2) ?
    C12 C13 Fe1 C21 . . . . -116.97(16) ?
    C14 C13 Fe1 C17 . . . . 81.8(2) ?
    C12 C13 Fe1 C17 . . . . -158.78(15) ?
    C12 C13 Fe1 C14 . . . . 119.4(2) ?
    C17 C21 Fe1 C16 . . . . 157.6(3) ?
    C20 C21 Fe1 C16 . . . . 37.9(4) ?
    C17 C21 Fe1 C18 . . . . 37.7(2) ?
    C20 C21 Fe1 C18 . . . . -82.0(2) ?
    C17 C21 Fe1 C15 . . . . -40.6(5) ?
    C20 C21 Fe1 C15 . . . . -160.3(4) ?
    C17 C21 Fe1 C12 . . . . -164.09(19) ?
    C20 C21 Fe1 C12 . . . . 76.2(2) ?
    C17 C21 Fe1 C20 . . . . 119.7(3) ?
    C17 C21 Fe1 C19 . . . . 82.4(2) ?
    C20 C21 Fe1 C19 . . . . -37.29(18) ?
    C17 C21 Fe1 C13 . . . . -120.1(2) ?
    C20 C21 Fe1 C13 . . . . 120.17(19) ?
    C20 C21 Fe1 C17 . . . . -119.7(3) ?
    C17 C21 Fe1 C14 . . . . -77.9(2) ?
    C20 C21 Fe1 C14 . . . . 162.37(18) ?
    C21 C17 Fe1 C16 . . . . -153.8(3) ?
    C18 C17 Fe1 C16 . . . . -34.7(5) ?
    C21 C17 Fe1 C18 . . . . -119.2(3) ?
    C21 C17 Fe1 C15 . . . . 165.6(2) ?
    C18 C17 Fe1 C15 . . . . -75.2(2) ?
    C21 C17 Fe1 C12 . . . . 39.1(4) ?
    C18 C17 Fe1 C12 . . . . 158.3(3) ?
    C21 C17 Fe1 C20 . . . . -37.31(18) ?
    C18 C17 Fe1 C20 . . . . 81.9(2) ?
    C21 C17 Fe1 C19 . . . . -80.6(2) ?
    C18 C17 Fe1 C19 . . . . 38.56(18) ?
    C21 C17 Fe1 C13 . . . . 79.6(2) ?
    C18 C17 Fe1 C13 . . . . -161.24(18) ?
    C18 C17 Fe1 C21 . . . . 119.2(3) ?
    C21 C17 Fe1 C14 . . . . 122.9(2) ?
    C18 C17 Fe1 C14 . . . . -118.0(2) ?
    C15 C14 Fe1 C16 . . . . -37.39(18) ?
    C13 C14 Fe1 C16 . . . . 82.35(19) ?
    C15 C14 Fe1 C18 . . . . 78.2(2) ?
    C13 C14 Fe1 C18 . . . . -162.08(19) ?
    C13 C14 Fe1 C15 . . . . 119.7(3) ?
    C15 C14 Fe1 C12 . . . . -81.75(19) ?
    C13 C14 Fe1 C12 . . . . 37.98(17) ?
    C15 C14 Fe1 C20 . . . . -159.1(4) ?
    C13 C14 Fe1 C20 . . . . -39.3(5) ?
    C15 C14 Fe1 C19 . . . . 39.4(4) ?
    C13 C14 Fe1 C19 . . . . 159.1(3) ?
    C15 C14 Fe1 C13 . . . . -119.7(3) ?
    C15 C14 Fe1 C21 . . . . 163.10(19) ?
    C13 C14 Fe1 C21 . . . . -77.2(2) ?
    C15 C14 Fe1 C17 . . . . 121.3(2) ?
    C13 C14 Fe1 C17 . . . . -118.96(19) ?
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
    C11 H11A N3 . 0.96 2.29 2.788(4) 111.8 y
    C8 H8A O3 7_665 0.97 2.57 3.476(3) 154 y
    C8 H8B O2 6_657 0.97 2.63 3.551(4) 158 y
    C21 H21 O2 6_657 0.93 2.46 3.136(4) 130 y