# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_utksc01
_database_code_depnum_ccdc_archive 'CCDC 1441263'
_audit_update_record             
;
2015-12-08 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;

_vrf_PLAT094_utksc01             
; 
PROBLEM: _B Ratio of Maximum / Minimum Residual Density .... 5.50 
RESPONSE: The large residual peak of 3.3 electrons per \%A^3^, located 
0.68 \%A from atom I1, is likely the result of residual absorption 
errors. 
;

_vrf_PLAT007_utksc01             
; 
PROBLEM: _G Number of Unrefined Donor-H Atoms .............. 1 
RESPONSE: Although the hydroxide hydrogen atom was located in the 
difference Fourier map, its positional and thermal parameters refined 
to slightly unreasonable values, perhaps due to minor disorder. It 
was ultimately refined with an ideal geometry and a relative isotropic 
displacement parameter. However, the model employed did allow the 
hydrogen atom to rotate about the C--O bond in order to find the site 
of maximum electron density. 
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            utksc01
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 Fe N2 O3, C H2 Cl2, I'
_chemical_formula_sum            'C14 H17 Cl2 Fe I N2 O3'
_chemical_formula_weight         514.95

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   29.269(4)
_cell_length_b                   38.689(5)
_cell_length_c                   6.4704(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7327.0(17)
_cell_formula_units_Z            16
_cell_measurement_temperature    100.0(5)
_cell_measurement_reflns_used    3743
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      37.60

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_F_000             4032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    2.814
_shelx_estimated_absorpt_T_min   0.334
_shelx_estimated_absorpt_T_max   0.631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2751
_exptl_absorpt_correction_T_max  0.4404
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD platform'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68174
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_k_max       67
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.745
_diffrn_reflns_theta_max         38.624
_diffrn_reflns_theta_full        37.785
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             9897
_reflns_number_gt                9001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.967

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SIR2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Although the hydroxide hydrogen atom was located in the 
 difference Fourier map, its positional and thermal parameters refined 
 to slightly unreasonable values, perhaps due to minor disorder. It 
 was ultimately refined with an ideal geometry and a relative isotropic 
 displacement parameter. However, the model employed did allow the 
 hydrogen atom to rotate about the C--O bond in order to find the site 
 of maximum electron density. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+4.4020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3830 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.006(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9897
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.02645(2) 0.07369(2) 0.37481(3) 0.02277(5) Uani 1 1 d . . . . .
Fe1 Fe 0.11359(2) 0.22928(2) 0.83614(6) 0.01590(7) Uani 1 1 d . . . . .
C1 C 0.13515(11) 0.26349(7) 0.9910(5) 0.0225(5) Uani 1 1 d . . . . .
O1 O 0.14747(10) 0.28642(6) 1.0894(5) 0.0324(5) Uani 1 1 d . . . . .
C2 C 0.05979(10) 0.23204(7) 0.9613(5) 0.0222(5) Uani 1 1 d . . . . .
O2 O 0.02518(8) 0.23438(7) 1.0417(6) 0.0328(6) Uani 1 1 d . . . . .
N1 N 0.17729(7) 0.18867(6) 1.1067(4) 0.0179(4) Uani 1 1 d . . . . .
N2 N 0.11388(8) 0.16158(6) 1.0654(4) 0.0170(4) Uani 1 1 d . . . . .
C3 C 0.13555(8) 0.19173(7) 1.0160(4) 0.0158(4) Uani 1 1 d . . . . .
O3 O 0.09369(9) 0.12354(6) 0.6936(4) 0.0271(5) Uani 1 1 d . . . . .
H3 H 0.0818 0.1123 0.5964 0.041 Uiso 1 1 calc R U . . .
C4 C 0.18187(10) 0.15732(8) 1.2081(5) 0.0214(5) Uani 1 1 d . . . . .
H4 H 0.2080 0.1493 1.2809 0.026 Uiso 1 1 calc R U . . .
C5 C 0.14156(10) 0.14031(7) 1.1827(5) 0.0208(5) Uani 1 1 d . . . . .
H5 H 0.1339 0.1181 1.2354 0.025 Uiso 1 1 calc R U . . .
C6 C 0.21413(10) 0.21433(8) 1.1050(6) 0.0248(5) Uani 1 1 d . . . . .
H6A H 0.2204 0.2214 0.9622 0.037 Uiso 1 1 calc R U . . .
H6B H 0.2417 0.2042 1.1656 0.037 Uiso 1 1 calc R U . . .
H6C H 0.2049 0.2346 1.1858 0.037 Uiso 1 1 calc R U . . .
C7 C 0.06769(9) 0.15069(7) 1.0045(5) 0.0194(5) Uani 1 1 d . . . . .
H7A H 0.0532 0.1694 0.9232 0.023 Uiso 1 1 calc R U . . .
H7B H 0.0491 0.1469 1.1301 0.023 Uiso 1 1 calc R U . . .
C8 C 0.06827(10) 0.11803(7) 0.8780(6) 0.0229(5) Uani 1 1 d . . . . .
H8A H 0.0823 0.0991 0.9590 0.027 Uiso 1 1 calc R U . . .
H8B H 0.0366 0.1112 0.8430 0.027 Uiso 1 1 calc R U . . .
C9 C 0.14266(12) 0.20002(8) 0.5928(5) 0.0264(6) Uani 1 1 d . . . . .
H9 H 0.1588 0.1789 0.6070 0.032 Uiso 1 1 calc R U . . .
C10 C 0.16202(10) 0.23307(9) 0.5976(5) 0.0251(5) Uani 1 1 d . . . . .
H10 H 0.1934 0.2382 0.6188 0.030 Uiso 1 1 calc R U . . .
C11 C 0.12618(12) 0.25786(8) 0.5651(6) 0.0264(6) Uani 1 1 d . . . . .
H11 H 0.1297 0.2823 0.5590 0.032 Uiso 1 1 calc R U . . .
C12 C 0.08491(12) 0.23952(10) 0.5441(6) 0.0291(6) Uani 1 1 d . . . . .
H12 H 0.0556 0.2494 0.5212 0.035 Uiso 1 1 calc R U . . .
C13 C 0.09485(13) 0.20335(9) 0.5632(6) 0.0299(6) Uani 1 1 d . . . . .
H13 H 0.0733 0.1850 0.5571 0.036 Uiso 1 1 calc R U . . .
C14 C 0.19779(12) 0.09669(8) 0.7665(6) 0.0252(5) Uani 1 1 d . . . . .
H14A H 0.2165 0.1180 0.7736 0.030 Uiso 1 1 calc R U . . .
H14B H 0.1654 0.1033 0.7868 0.030 Uiso 1 1 calc R U . . .
Cl1 Cl 0.20432(4) 0.07745(2) 0.51973(15) 0.03390(18) Uani 1 1 d . . . . .
Cl2 Cl 0.21460(4) 0.06811(2) 0.96625(16) 0.03328(18) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C2 1.774(3) . ?
Fe1 C1 1.776(3) . ?
Fe1 C3 1.969(3) . ?
Fe1 C10 2.101(3) . ?
Fe1 C13 2.104(4) . ?
Fe1 C12 2.105(4) . ?
Fe1 C11 2.106(3) . ?
Fe1 C9 2.118(3) . ?
C1 O1 1.150(4) . ?
C2 O2 1.142(4) . ?
N1 C3 1.361(3) . ?
N1 C4 1.385(4) . ?
N1 C6 1.466(4) . ?
N2 C3 1.366(3) . ?
N2 C5 1.382(4) . ?
N2 C7 1.470(4) . ?
O3 C8 1.423(4) . ?
O3 H3 0.8400 . ?
C4 C5 1.361(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.506(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.399(5) . ?
C9 C13 1.418(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.437(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.407(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.435(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 Cl2 1.771(4) . ?
C14 Cl1 1.772(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Fe1 C1 90.76(14) . . ?
C2 Fe1 C3 93.69(13) . . ?
C1 Fe1 C3 95.75(13) . . ?
C2 Fe1 C10 158.47(15) . . ?
C1 Fe1 C10 97.04(13) . . ?
C3 Fe1 C10 105.39(12) . . ?
C2 Fe1 C13 100.39(15) . . ?
C1 Fe1 C13 157.17(15) . . ?
C3 Fe1 C13 103.26(13) . . ?
C10 Fe1 C13 65.95(14) . . ?
C2 Fe1 C12 92.55(15) . . ?
C1 Fe1 C12 120.52(15) . . ?
C3 Fe1 C12 143.07(13) . . ?
C10 Fe1 C12 66.20(13) . . ?
C13 Fe1 C12 39.86(15) . . ?
C2 Fe1 C11 120.26(14) . . ?
C1 Fe1 C11 90.93(14) . . ?
C3 Fe1 C11 145.33(12) . . ?
C10 Fe1 C11 39.95(13) . . ?
C13 Fe1 C11 66.23(14) . . ?
C12 Fe1 C11 39.05(14) . . ?
C2 Fe1 C9 136.73(15) . . ?
C1 Fe1 C9 132.46(14) . . ?
C3 Fe1 C9 85.06(12) . . ?
C10 Fe1 C9 38.74(13) . . ?
C13 Fe1 C9 39.25(15) . . ?
C12 Fe1 C9 66.01(14) . . ?
C11 Fe1 C9 65.87(13) . . ?
O1 C1 Fe1 177.1(3) . . ?
O2 C2 Fe1 178.9(3) . . ?
C3 N1 C4 111.5(2) . . ?
C3 N1 C6 126.7(2) . . ?
C4 N1 C6 121.7(2) . . ?
C3 N2 C5 111.4(2) . . ?
C3 N2 C7 127.5(2) . . ?
C5 N2 C7 121.0(2) . . ?
N1 C3 N2 104.0(2) . . ?
N1 C3 Fe1 127.76(19) . . ?
N2 C3 Fe1 128.08(19) . . ?
C8 O3 H3 109.5 . . ?
C5 C4 N1 106.4(3) . . ?
C5 C4 H4 126.8 . . ?
N1 C4 H4 126.8 . . ?
C4 C5 N2 106.6(3) . . ?
C4 C5 H5 126.7 . . ?
N2 C5 H5 126.7 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 112.1(2) . . ?
N2 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O3 C8 C7 109.6(2) . . ?
O3 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
O3 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C13 108.6(3) . . ?
C10 C9 Fe1 69.97(18) . . ?
C13 C9 Fe1 69.84(19) . . ?
C10 C9 H9 125.7 . . ?
C13 C9 H9 125.7 . . ?
Fe1 C9 H9 126.1 . . ?
C9 C10 C11 108.1(3) . . ?
C9 C10 Fe1 71.29(18) . . ?
C11 C10 Fe1 70.21(18) . . ?
C9 C10 H10 125.9 . . ?
C11 C10 H10 125.9 . . ?
Fe1 C10 H10 124.2 . . ?
C12 C11 C10 107.7(3) . . ?
C12 C11 Fe1 70.47(19) . . ?
C10 C11 Fe1 69.84(18) . . ?
C12 C11 H11 126.1 . . ?
C10 C11 H11 126.1 . . ?
Fe1 C11 H11 125.1 . . ?
C11 C12 C13 108.0(3) . . ?
C11 C12 Fe1 70.48(19) . . ?
C13 C12 Fe1 70.0(2) . . ?
C11 C12 H12 126.0 . . ?
C13 C12 H12 126.0 . . ?
Fe1 C12 H12 125.1 . . ?
C9 C13 C12 107.5(3) . . ?
C9 C13 Fe1 70.90(19) . . ?
C12 C13 Fe1 70.1(2) . . ?
C9 C13 H13 126.3 . . ?
C12 C13 H13 126.3 . . ?
Fe1 C13 H13 124.3 . . ?
Cl2 C14 Cl1 111.43(17) . . ?
Cl2 C14 H14A 109.3 . . ?
Cl1 C14 H14A 109.3 . . ?
Cl2 C14 H14B 109.3 . . ?
Cl1 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C3 N2 0.7(3) . . . . ?
C6 N1 C3 N2 -178.9(3) . . . . ?
C4 N1 C3 Fe1 -174.8(2) . . . . ?
C6 N1 C3 Fe1 5.7(4) . . . . ?
C5 N2 C3 N1 -0.3(3) . . . . ?
C7 N2 C3 N1 -179.0(3) . . . . ?
C5 N2 C3 Fe1 175.1(2) . . . . ?
C7 N2 C3 Fe1 -3.5(4) . . . . ?
C3 N1 C4 C5 -0.8(3) . . . . ?
C6 N1 C4 C5 178.8(3) . . . . ?
N1 C4 C5 N2 0.6(3) . . . . ?
C3 N2 C5 C4 -0.2(3) . . . . ?
C7 N2 C5 C4 178.6(3) . . . . ?
C3 N2 C7 C8 119.0(3) . . . . ?
C5 N2 C7 C8 -59.6(4) . . . . ?
N2 C7 C8 O3 -60.8(3) . . . . ?
C13 C9 C10 C11 -1.5(4) . . . . ?
Fe1 C9 C10 C11 -60.9(2) . . . . ?
C13 C9 C10 Fe1 59.3(2) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
Fe1 C10 C11 C12 -60.6(2) . . . . ?
C9 C10 C11 Fe1 61.5(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
Fe1 C11 C12 C13 -60.2(2) . . . . ?
C10 C11 C12 Fe1 60.2(2) . . . . ?
C10 C9 C13 C12 1.5(4) . . . . ?
Fe1 C9 C13 C12 60.9(2) . . . . ?
C10 C9 C13 Fe1 -59.4(2) . . . . ?
C11 C12 C13 C9 -0.9(4) . . . . ?
Fe1 C12 C13 C9 -61.4(2) . . . . ?
C11 C12 C13 Fe1 60.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 I1 0.84 2.63 3.442(2) 163.3 .

_refine_diff_density_max         3.279
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.140

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_utksc03
_database_code_depnum_ccdc_archive 'CCDC 1441264'
_audit_update_record             
;
2015-12-08 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            utksc03
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H30 Fe N2 O3'
_chemical_formula_sum            'C25 H30 Fe N2 O3'
_chemical_formula_weight         462.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   10.8596(11)
_cell_length_b                   8.8254(9)
_cell_length_c                   23.959(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.211(2)
_cell_angle_gamma                90
_cell_volume                     2252.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(5)
_cell_measurement_reflns_used    3991
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      37.77

_exptl_crystal_description       block
_exptl_crystal_colour            red-orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.698
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6728
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD platform'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54838
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.939
_diffrn_reflns_theta_max         38.664
_diffrn_reflns_theta_full        37.785
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             12380
_reflns_number_gt                9352
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SIR2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.5897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12380
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.22730(2) 0.38977(2) 0.43741(2) 0.01269(4) Uani 1 1 d . . . . .
O1 O 0.42388(12) 0.19630(15) 0.50000(5) 0.0418(3) Uani 1 1 d . . . . .
O2 O 0.40069(10) 0.50427(12) 0.36839(5) 0.0288(2) Uani 1 1 d . . . . .
O3 O -0.01715(8) 0.75412(10) 0.42030(3) 0.01678(15) Uani 1 1 d . . . . .
N1 N 0.26938(9) 0.56275(12) 0.54763(4) 0.01560(16) Uani 1 1 d . . . . .
N2 N 0.23001(9) 0.71372(11) 0.47583(4) 0.01399(15) Uani 1 1 d . . . . .
C1 C 0.34772(13) 0.27732(16) 0.47733(6) 0.0242(2) Uani 1 1 d . . . . .
C2 C 0.33123(11) 0.46592(14) 0.39587(5) 0.0191(2) Uani 1 1 d . . . . .
C3 C 0.24521(10) 0.56458(13) 0.48970(4) 0.01322(17) Uani 1 1 d . . . . .
C4 C 0.26790(12) 0.70815(15) 0.56922(5) 0.0197(2) Uani 1 1 d . . . . .
H4 H 0.2817 0.7359 0.6083 0.024 Uiso 1 1 calc R U . . .
C5 C 0.24311(12) 0.80272(14) 0.52429(5) 0.0194(2) Uani 1 1 d . . . . .
H5 H 0.2360 0.9099 0.5256 0.023 Uiso 1 1 calc R U . . .
C6 C 0.29062(12) 0.42856(15) 0.58421(5) 0.0203(2) Uani 1 1 d . . . . .
H6A H 0.2197 0.3587 0.5739 0.030 Uiso 1 1 calc R U . . .
H6B H 0.2983 0.4592 0.6241 0.030 Uiso 1 1 calc R U . . .
H6C H 0.3681 0.3780 0.5792 0.030 Uiso 1 1 calc R U . . .
C7 C 0.19987(10) 0.77879(12) 0.41946(4) 0.01294(16) Uani 1 1 d . . . . .
C8 C 0.29830(10) 0.83353(12) 0.39579(5) 0.01382(17) Uani 1 1 d . . . . .
H8 H 0.3822 0.8229 0.4161 0.017 Uiso 1 1 calc R U . . .
C9 C 0.27543(10) 0.90377(12) 0.34265(5) 0.01306(16) Uani 1 1 d . . . . .
C10 C 0.14916(10) 0.91327(11) 0.31498(4) 0.01240(16) Uani 1 1 d . . . . .
H10 H 0.1315 0.9571 0.2781 0.015 Uiso 1 1 calc R U . . .
C11 C 0.04798(9) 0.86290(11) 0.33794(4) 0.01173(16) Uani 1 1 d . . . . .
C12 C 0.07022(10) 0.79572(12) 0.39408(4) 0.01253(16) Uani 1 1 d . . . . .
C13 C 0.38419(10) 0.96308(13) 0.31656(5) 0.01500(18) Uani 1 1 d . . . . .
C14 C 0.46482(12) 0.83003(16) 0.30300(6) 0.0239(2) Uani 1 1 d . . . . .
H14A H 0.4119 0.7584 0.2777 0.036 Uiso 1 1 calc R U . . .
H14B H 0.5029 0.7785 0.3384 0.036 Uiso 1 1 calc R U . . .
H14C H 0.5311 0.8683 0.2842 0.036 Uiso 1 1 calc R U . . .
C15 C 0.46711(13) 1.07039(17) 0.35793(6) 0.0263(3) Uani 1 1 d . . . . .
H15A H 0.4169 1.1567 0.3663 0.039 Uiso 1 1 calc R U . . .
H15B H 0.5363 1.1069 0.3407 0.039 Uiso 1 1 calc R U . . .
H15C H 0.5012 1.0162 0.3933 0.039 Uiso 1 1 calc R U . . .
C16 C 0.33800(12) 1.04979(18) 0.26105(6) 0.0254(3) Uani 1 1 d . . . . .
H16A H 0.2846 1.1343 0.2682 0.038 Uiso 1 1 calc R U . . .
H16B H 0.2896 0.9814 0.2328 0.038 Uiso 1 1 calc R U . . .
H16C H 0.4102 1.0892 0.2467 0.038 Uiso 1 1 calc R U . . .
C17 C -0.08745(10) 0.88290(12) 0.30545(5) 0.01384(17) Uani 1 1 d . . . . .
C18 C -0.15876(11) 0.98979(15) 0.33887(6) 0.0209(2) Uani 1 1 d . . . . .
H18A H -0.1178 1.0892 0.3428 0.031 Uiso 1 1 calc R U . . .
H18B H -0.1582 0.9473 0.3767 0.031 Uiso 1 1 calc R U . . .
H18C H -0.2456 1.0009 0.3184 0.031 Uiso 1 1 calc R U . . .
C19 C -0.15424(10) 0.72843(14) 0.29769(5) 0.01744(19) Uani 1 1 d . . . . .
H19A H -0.1132 0.6633 0.2737 0.026 Uiso 1 1 calc R U . . .
H19B H -0.2424 0.7431 0.2795 0.026 Uiso 1 1 calc R U . . .
H19C H -0.1497 0.6805 0.3349 0.026 Uiso 1 1 calc R U . . .
C20 C -0.09480(11) 0.94892(15) 0.24557(5) 0.0202(2) Uani 1 1 d . . . . .
H20A H -0.0580 1.0507 0.2485 0.030 Uiso 1 1 calc R U . . .
H20B H -0.1828 0.9546 0.2261 0.030 Uiso 1 1 calc R U . . .
H20C H -0.0482 0.8836 0.2239 0.030 Uiso 1 1 calc R U . . .
C21 C 0.03149(11) 0.41863(14) 0.43056(5) 0.0176(2) Uani 1 1 d . . . . .
H21 H -0.0079 0.4982 0.4472 0.021 Uiso 1 1 calc R U . . .
C22 C 0.06917(11) 0.27665(14) 0.45654(5) 0.0185(2) Uani 1 1 d . . . . .
H22 H 0.0604 0.2450 0.4935 0.022 Uiso 1 1 calc R U . . .
C23 C 0.12279(12) 0.19039(13) 0.41659(5) 0.0185(2) Uani 1 1 d . . . . .
H23 H 0.1552 0.0904 0.4223 0.022 Uiso 1 1 calc R U . . .
C24 C 0.11934(11) 0.27911(13) 0.36736(5) 0.01731(19) Uani 1 1 d . . . . .
H24 H 0.1495 0.2495 0.3343 0.021 Uiso 1 1 calc R U . . .
C25 C 0.06245(11) 0.42169(13) 0.37585(5) 0.01725(19) Uani 1 1 d . . . . .
H25 H 0.0481 0.5033 0.3496 0.021 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C1 1.7673(13) . ?
Fe1 C2 1.7756(12) . ?
Fe1 C3 1.9730(11) . ?
Fe1 C24 2.0928(11) . ?
Fe1 C23 2.1007(12) . ?
Fe1 C25 2.1053(12) . ?
Fe1 C22 2.1123(12) . ?
Fe1 C21 2.1161(12) . ?
O1 C1 1.1470(17) . ?
O2 C2 1.1446(15) . ?
O3 C12 1.2890(13) . ?
N1 C3 1.3617(14) . ?
N1 C4 1.3847(16) . ?
N1 C6 1.4646(15) . ?
N2 C3 1.3597(14) . ?
N2 C5 1.3860(15) . ?
N2 C7 1.4452(14) . ?
C4 C5 1.3474(17) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3905(15) . ?
C7 C12 1.4288(15) . ?
C8 C9 1.3942(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.4048(15) . ?
C9 C13 1.5319(14) . ?
C10 C11 1.3937(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.4467(15) . ?
C11 C17 1.5345(15) . ?
C13 C15 1.5307(17) . ?
C13 C16 1.5318(17) . ?
C13 C14 1.5367(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C20 1.5360(16) . ?
C17 C19 1.5384(16) . ?
C17 C18 1.5402(16) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C25 1.4153(17) . ?
C21 C22 1.4234(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.4321(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.4103(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.4336(17) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Fe1 C2 91.82(6) . . ?
C1 Fe1 C3 97.14(6) . . ?
C2 Fe1 C3 93.73(5) . . ?
C1 Fe1 C24 114.34(6) . . ?
C2 Fe1 C24 92.59(5) . . ?
C3 Fe1 C24 147.65(5) . . ?
C1 Fe1 C23 88.10(6) . . ?
C2 Fe1 C23 123.84(5) . . ?
C3 Fe1 C23 141.97(5) . . ?
C24 Fe1 C23 39.30(5) . . ?
C1 Fe1 C25 153.27(6) . . ?
C2 Fe1 C25 95.93(5) . . ?
C3 Fe1 C25 107.79(5) . . ?
C24 Fe1 C25 39.93(5) . . ?
C23 Fe1 C25 66.37(5) . . ?
C1 Fe1 C22 99.46(6) . . ?
C2 Fe1 C22 158.86(5) . . ?
C3 Fe1 C22 102.46(5) . . ?
C24 Fe1 C22 66.49(5) . . ?
C23 Fe1 C22 39.75(5) . . ?
C25 Fe1 C22 66.35(5) . . ?
C1 Fe1 C21 137.41(6) . . ?
C2 Fe1 C21 130.52(5) . . ?
C3 Fe1 C21 85.90(4) . . ?
C24 Fe1 C21 66.18(5) . . ?
C23 Fe1 C21 66.05(5) . . ?
C25 Fe1 C21 39.18(5) . . ?
C22 Fe1 C21 39.34(5) . . ?
C3 N1 C4 110.85(10) . . ?
C3 N1 C6 126.60(10) . . ?
C4 N1 C6 122.53(10) . . ?
C3 N2 C5 110.86(9) . . ?
C3 N2 C7 127.42(9) . . ?
C5 N2 C7 121.69(10) . . ?
O1 C1 Fe1 174.79(13) . . ?
O2 C2 Fe1 174.95(11) . . ?
N2 C3 N1 104.52(9) . . ?
N2 C3 Fe1 127.55(7) . . ?
N1 C3 Fe1 127.86(8) . . ?
C5 C4 N1 106.89(10) . . ?
C5 C4 H4 126.6 . . ?
N1 C4 H4 126.6 . . ?
C4 C5 N2 106.88(11) . . ?
C4 C5 H5 126.6 . . ?
N2 C5 H5 126.6 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 124.20(10) . . ?
C8 C7 N2 117.83(9) . . ?
C12 C7 N2 117.69(9) . . ?
C7 C8 C9 120.83(10) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 116.21(9) . . ?
C8 C9 C13 120.66(9) . . ?
C10 C9 C13 123.12(9) . . ?
C11 C10 C9 124.53(10) . . ?
C11 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
C10 C11 C12 119.72(9) . . ?
C10 C11 C17 120.96(9) . . ?
C12 C11 C17 119.28(9) . . ?
O3 C12 C7 121.37(9) . . ?
O3 C12 C11 124.35(9) . . ?
C7 C12 C11 114.28(9) . . ?
C15 C13 C16 107.77(11) . . ?
C15 C13 C9 110.50(9) . . ?
C16 C13 C9 112.13(9) . . ?
C15 C13 C14 108.78(10) . . ?
C16 C13 C14 107.59(10) . . ?
C9 C13 C14 109.96(9) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 C20 112.83(9) . . ?
C11 C17 C19 110.01(9) . . ?
C20 C17 C19 106.60(9) . . ?
C11 C17 C18 109.63(9) . . ?
C20 C17 C18 108.25(10) . . ?
C19 C17 C18 109.43(9) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C25 C21 C22 108.77(10) . . ?
C25 C21 Fe1 70.00(7) . . ?
C22 C21 Fe1 70.18(7) . . ?
C25 C21 H21 125.6 . . ?
C22 C21 H21 125.6 . . ?
Fe1 C21 H21 125.8 . . ?
C21 C22 C23 107.18(10) . . ?
C21 C22 Fe1 70.47(7) . . ?
C23 C22 Fe1 69.69(7) . . ?
C21 C22 H22 126.4 . . ?
C23 C22 H22 126.4 . . ?
Fe1 C22 H22 125.0 . . ?
C24 C23 C22 108.40(11) . . ?
C24 C23 Fe1 70.05(7) . . ?
C22 C23 Fe1 70.56(7) . . ?
C24 C23 H23 125.8 . . ?
C22 C23 H23 125.8 . . ?
Fe1 C23 H23 125.2 . . ?
C23 C24 C25 108.10(10) . . ?
C23 C24 Fe1 70.65(7) . . ?
C25 C24 Fe1 70.50(6) . . ?
C23 C24 H24 126.0 . . ?
C25 C24 H24 126.0 . . ?
Fe1 C24 H24 124.5 . . ?
C21 C25 C24 107.54(10) . . ?
C21 C25 Fe1 70.82(7) . . ?
C24 C25 Fe1 69.56(6) . . ?
C21 C25 H25 126.2 . . ?
C24 C25 H25 126.2 . . ?
Fe1 C25 H25 125.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C3 N1 -0.67(12) . . . . ?
C7 N2 C3 N1 -178.59(10) . . . . ?
C5 N2 C3 Fe1 176.46(8) . . . . ?
C7 N2 C3 Fe1 -1.46(16) . . . . ?
C4 N1 C3 N2 0.60(12) . . . . ?
C6 N1 C3 N2 178.71(10) . . . . ?
C4 N1 C3 Fe1 -176.51(8) . . . . ?
C6 N1 C3 Fe1 1.60(16) . . . . ?
C3 N1 C4 C5 -0.31(14) . . . . ?
C6 N1 C4 C5 -178.52(11) . . . . ?
N1 C4 C5 N2 -0.11(14) . . . . ?
C3 N2 C5 C4 0.50(14) . . . . ?
C7 N2 C5 C4 178.55(10) . . . . ?
C3 N2 C7 C8 -97.03(13) . . . . ?
C5 N2 C7 C8 85.26(13) . . . . ?
C3 N2 C7 C12 88.83(13) . . . . ?
C5 N2 C7 C12 -88.89(13) . . . . ?
C12 C7 C8 C9 -3.41(17) . . . . ?
N2 C7 C8 C9 -177.14(10) . . . . ?
C7 C8 C9 C10 -0.85(15) . . . . ?
C7 C8 C9 C13 -179.63(10) . . . . ?
C8 C9 C10 C11 2.44(16) . . . . ?
C13 C9 C10 C11 -178.81(10) . . . . ?
C9 C10 C11 C12 0.13(16) . . . . ?
C9 C10 C11 C17 177.85(10) . . . . ?
C8 C7 C12 O3 -173.96(10) . . . . ?
N2 C7 C12 O3 -0.22(15) . . . . ?
C8 C7 C12 C11 5.72(15) . . . . ?
N2 C7 C12 C11 179.46(9) . . . . ?
C10 C11 C12 O3 175.68(10) . . . . ?
C17 C11 C12 O3 -2.08(16) . . . . ?
C10 C11 C12 C7 -3.99(14) . . . . ?
C17 C11 C12 C7 178.24(9) . . . . ?
C8 C9 C13 C15 -54.07(14) . . . . ?
C10 C9 C13 C15 127.23(12) . . . . ?
C8 C9 C13 C16 -174.32(11) . . . . ?
C10 C9 C13 C16 6.98(15) . . . . ?
C8 C9 C13 C14 66.03(14) . . . . ?
C10 C9 C13 C14 -112.67(12) . . . . ?
C10 C11 C17 C20 4.91(14) . . . . ?
C12 C11 C17 C20 -177.36(10) . . . . ?
C10 C11 C17 C19 123.81(10) . . . . ?
C12 C11 C17 C19 -58.46(12) . . . . ?
C10 C11 C17 C18 -115.81(11) . . . . ?
C12 C11 C17 C18 61.92(12) . . . . ?
C25 C21 C22 C23 -0.75(13) . . . . ?
Fe1 C21 C22 C23 -60.32(8) . . . . ?
C25 C21 C22 Fe1 59.57(8) . . . . ?
C21 C22 C23 C24 0.74(13) . . . . ?
Fe1 C22 C23 C24 -60.08(8) . . . . ?
C21 C22 C23 Fe1 60.82(8) . . . . ?
C22 C23 C24 C25 -0.45(14) . . . . ?
Fe1 C23 C24 C25 -60.86(8) . . . . ?
C22 C23 C24 Fe1 60.41(8) . . . . ?
C22 C21 C25 C24 0.47(13) . . . . ?
Fe1 C21 C25 C24 60.16(8) . . . . ?
C22 C21 C25 Fe1 -59.69(8) . . . . ?
C23 C24 C25 C21 -0.01(13) . . . . ?
Fe1 C24 C25 C21 -60.96(8) . . . . ?
C23 C24 C25 Fe1 60.95(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A O3 0.98 2.44 3.3624(15) 156.1 3_566
C22 H22 O3 0.95 2.21 3.1222(14) 161.7 3_566

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.087

_shelxl_version_number           2014-2

