# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_ds258_0m_new
_database_code_depnum_ccdc_archive 'CCDC 1830689'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-30 downloaded from the CCDC.
;
_audit_creation_date             2018-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C60 H48 Fe4 N18 O6), 3(N1 O3)'
_chemical_formula_sum            'C60 H48 Fe4 N21 O15'
_chemical_formula_weight         1526.61
_chemical_melting_point          ?
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'
Fe Fe 0.3463 0.8444 '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'

_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.
;
_space_group_crystal_system      cubic
_space_group_IT_number           205
_space_group_name_H-M_alt        'P a -3'
_space_group_name_Hall           '-P 2ac 2ab 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'z, x, y'
'y, z, x'
'-y+1/2, -z, x+1/2'
'z+1/2, -x+1/2, -y'
'-y, z+1/2, -x+1/2'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y+1/2, -z+1/2, -x'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'-z, -x, -y'
'-y, -z, -x'
'y-1/2, z, -x-1/2'
'-z-1/2, x-1/2, y'
'y, -z-1/2, x-1/2'
'z-1/2, x, -y-1/2'
'z, -x-1/2, y-1/2'
'-y-1/2, z-1/2, x'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.080(2)
_cell_length_b                   23.080(2)
_cell_length_c                   23.080(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     12295(4)
_cell_formula_units_Z            7.99992
_cell_measurement_reflns_used    1217
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      2.50
_cell_measurement_theta_min      23.41
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.737
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  0.7280
_exptl_absorpt_correction_T_min  0.6569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             6232
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1443
_diffrn_reflns_av_unetI/netI     0.1233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            21172
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         1.765
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2783
_reflns_number_total             4739
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4739
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1636
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N3-H3 = N6-H6
 0.91 with sigma of 0.02
 N9-O10 = N9-O11 = N9-O12
 1.25 with sigma of 0.02
 O10-O11 = O11-O12 = O12-O10
 2.16 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O10) \\sim Ueq, Uanis(O11) \\sim Ueq, Uanis(O12) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
4. Others
 Fixed Sof: O10(0.3333) O11(0.3333) O12(0.3333)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13),
  C14(H14), C15(H15), C17(H17), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.88910(2) 0.38910(2) 0.11090(2) 0.0179(2) Uani 1 3 d S T P . .
Fe2 Fe 0.79151(3) 0.48913(3) 0.11117(3) 0.01997(19) Uani 1 1 d . . . . .
O1 O 0.85892(12) 0.45218(12) 0.05986(12) 0.0234(7) Uani 1 1 d . . . . .
O2 O 0.82645(12) 0.42055(12) 0.16220(11) 0.0201(6) Uani 1 1 d . . . . .
O8 O 0.80605(14) 0.74626(14) 0.23144(14) 0.0339(8) Uani 1 1 d . . . . .
O9 O 0.54045(13) 0.42537(12) 0.00179(12) 0.0259(7) Uani 1 1 d . . . . .
O10 O 0.8964(7) 0.6369(6) 0.4088(6) 0.085(5) Uani 0.3333 1 d D U . . .
O11 O 0.8196(5) 0.6181(6) 0.3847(6) 0.063(4) Uani 0.3333 1 d D U . . .
O12 O 0.8662(5) 0.6559(5) 0.3111(4) 0.046(3) Uani 0.3333 1 d D U . . .
N1 N 0.75235(15) 0.46505(14) 0.02848(15) 0.0215(8) Uani 1 1 d . . . . .
N2 N 0.69972(15) 0.48989(15) 0.12624(15) 0.0225(8) Uani 1 1 d . . . . .
N3 N 0.61195(16) 0.47343(17) 0.09162(18) 0.0300(9) Uani 1 1 d D . . . .
N4 N 0.80589(15) 0.52497(15) 0.19623(14) 0.0203(8) Uani 1 1 d . . . . .
N5 N 0.79571(15) 0.58092(15) 0.09747(15) 0.0218(8) Uani 1 1 d . . . . .
N6 N 0.80025(16) 0.66750(15) 0.13792(16) 0.0256(8) Uani 1 1 d D . . . .
N7 N 0.76390(15) 0.73610(15) 0.26390(15) 0.0260(14) Uani 1 3 d S T P . .
N8 N 0.53775(14) 0.46225(14) -0.03775(14) 0.0224(14) Uani 1 3 d S T P . .
N9 N 0.8634(2) 0.6366(2) 0.3634(2) 0.053(2) Uani 1 3 d DS T P . .
C1 C 0.84858(19) 0.44974(18) 0.00200(18) 0.0241(10) Uani 1 1 d . . . . .
C2 C 0.8928(2) 0.44398(19) -0.03872(19) 0.0312(11) Uani 1 1 d . . . . .
H2 H 0.931338 0.442631 -0.026954 0.037 Uiso 1 1 calc R . . . .
C3 C 0.8786(2) 0.4403(2) -0.0973(2) 0.0390(13) Uani 1 1 d . . . . .
H3A H 0.907829 0.435763 -0.124646 0.047 Uiso 1 1 calc R . . . .
C4 C 0.8219(2) 0.4432(2) -0.1149(2) 0.0377(12) Uani 1 1 d . . . . .
H4 H 0.813109 0.440271 -0.154151 0.045 Uiso 1 1 calc R . . . .
C5 C 0.7778(2) 0.45035(19) -0.07540(19) 0.0310(11) Uani 1 1 d . . . . .
H5 H 0.739502 0.452389 -0.087911 0.037 Uiso 1 1 calc R . . . .
C6 C 0.79071(19) 0.45456(18) -0.01646(18) 0.0248(10) Uani 1 1 d . . . . .
C7 C 0.69731(19) 0.45882(17) 0.02676(19) 0.0243(10) Uani 1 1 d . . . . .
H7 H 0.677456 0.446391 -0.006024 0.029 Uiso 1 1 calc R . . . .
C8 C 0.66906(18) 0.47299(17) 0.08069(19) 0.0237(10) Uani 1 1 d . . . . .
C9 C 0.6057(2) 0.4914(2) 0.1475(2) 0.0351(12) Uani 1 1 d . . . . .
H9 H 0.571183 0.495838 0.167691 0.042 Uiso 1 1 calc R . . . .
C10 C 0.66026(19) 0.5015(2) 0.1678(2) 0.0305(11) Uani 1 1 d . . . . .
H10 H 0.668991 0.514489 0.204977 0.037 Uiso 1 1 calc R . . . .
C11 C 0.82490(17) 0.42858(18) 0.21995(17) 0.0189(9) Uani 1 1 d . . . . .
C12 C 0.83202(18) 0.38328(19) 0.25948(18) 0.0244(9) Uani 1 1 d . . . . .
H12 H 0.837466 0.345576 0.246345 0.029 Uiso 1 1 calc R . . . .
C13 C 0.83092(18) 0.3950(2) 0.31873(19) 0.0286(10) Uani 1 1 d . . . . .
H13 H 0.834877 0.364794 0.345133 0.034 Uiso 1 1 calc R . . . .
C14 C 0.82394(18) 0.4513(2) 0.33867(19) 0.0265(10) Uani 1 1 d . . . . .
H14 H 0.824541 0.458923 0.378235 0.032 Uiso 1 1 calc R . . . .
C15 C 0.81618(18) 0.4958(2) 0.29997(17) 0.0231(9) Uani 1 1 d . . . . .
H15 H 0.811510 0.533434 0.313465 0.028 Uiso 1 1 calc R . . . .
C16 C 0.81524(17) 0.48494(17) 0.24104(18) 0.0195(9) Uani 1 1 d . . . . .
C17 C 0.80495(19) 0.57973(19) 0.20141(19) 0.0262(10) Uani 1 1 d . . . . .
H17 H 0.807981 0.598480 0.236948 0.031 Uiso 1 1 calc R . . . .
C18 C 0.79876(18) 0.61011(17) 0.14744(19) 0.0229(9) Uani 1 1 d . . . . .
C19 C 0.7989(2) 0.6762(2) 0.0794(2) 0.0318(11) Uani 1 1 d . . . . .
H19 H 0.799422 0.711509 0.060074 0.038 Uiso 1 1 calc R . . . .
C20 C 0.79647(19) 0.62180(19) 0.0549(2) 0.0282(10) Uani 1 1 d . . . . .
H20 H 0.795530 0.614169 0.015318 0.034 Uiso 1 1 calc R . . . .
H3 H 0.5832(15) 0.4618(19) 0.0678(17) 0.035(13) Uiso 1 1 d D . . . .
H6 H 0.801(2) 0.6952(18) 0.1654(18) 0.052(17) Uiso 1 1 d 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 O1 1.998(3) . ?
Fe1 O1 1.998(3) 9_556 ?
Fe1 O1 1.998(3) 8_645 ?
Fe1 O2 2.005(3) . ?
Fe1 O2 2.005(3) 8_645 ?
Fe1 O2 2.005(3) 9_556 ?
Fe2 O1 2.133(3) . ?
Fe2 O2 2.131(3) . ?
Fe2 N1 2.184(3) . ?
Fe2 N2 2.147(3) . ?
Fe2 N4 2.156(3) . ?
Fe2 N5 2.144(4) . ?
O1 C1 1.358(5) . ?
O2 C11 1.346(5) . ?
O8 N7 1.250(3) . ?
O9 N8 1.249(3) . ?
O10 O10 1.33(2) 5_566 ?
O10 O10 1.33(2) 4_664 ?
O10 O11 1.212(18) 5_566 ?
O10 N9 1.295(12) . ?
O11 O12 1.780(17) 4_664 ?
O11 O12 1.022(14) 5_566 ?
O11 N9 1.202(11) . ?
O12 O12 1.567(18) 4_664 ?
O12 O12 1.567(18) 5_566 ?
O12 N9 1.287(10) . ?
N1 C6 1.385(5) . ?
N1 C7 1.279(5) . ?
N2 C8 1.326(5) . ?
N2 C10 1.350(6) . ?
N3 C8 1.342(6) . ?
N3 C9 1.361(6) . ?
N3 H3 0.903(19) . ?
N4 C16 1.403(5) . ?
N4 C17 1.270(5) . ?
N5 C18 1.338(5) . ?
N5 C20 1.363(6) . ?
N6 C18 1.343(5) . ?
N6 C19 1.366(6) . ?
N6 H6 0.900(19) . ?
C1 C2 1.394(6) . ?
C1 C6 1.406(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(6) . ?
C3 H3A 0.9300 . ?
C3 C4 1.373(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.443(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(6) . ?
C11 C16 1.407(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.437(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(6) . ?
C20 H20 0.9300 . ?

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
O1 Fe1 O1 91.72(12) . 9_556 ?
O1 Fe1 O1 91.72(12) . 8_645 ?
O1 Fe1 O1 91.72(12) 9_556 8_645 ?
O1 Fe1 O2 96.10(11) . 8_645 ?
O1 Fe1 O2 96.10(11) 8_645 9_556 ?
O1 Fe1 O2 80.38(11) 8_645 8_645 ?
O1 Fe1 O2 169.02(11) 9_556 8_645 ?
O1 Fe1 O2 80.38(11) . . ?
O1 Fe1 O2 169.02(11) . 9_556 ?
O1 Fe1 O2 96.09(11) 9_556 . ?
O1 Fe1 O2 169.02(11) 8_645 . ?
O1 Fe1 O2 80.38(11) 9_556 9_556 ?
O2 Fe1 O2 92.81(11) . 8_645 ?
O2 Fe1 O2 92.81(11) . 9_556 ?
O2 Fe1 O2 92.81(11) 8_645 9_556 ?
O1 Fe2 N1 73.43(12) . . ?
O1 Fe2 N2 144.37(12) . . ?
O1 Fe2 N4 123.14(12) . . ?
O1 Fe2 N5 106.27(12) . . ?
O2 Fe2 O1 74.57(10) . . ?
O2 Fe2 N1 116.77(12) . . ?
O2 Fe2 N2 106.85(12) . . ?
O2 Fe2 N4 73.95(12) . . ?
O2 Fe2 N5 142.96(12) . . ?
N2 Fe2 N1 74.65(13) . . ?
N2 Fe2 N4 90.08(13) . . ?
N4 Fe2 N1 163.18(13) . . ?
N5 Fe2 N1 98.12(13) . . ?
N5 Fe2 N2 93.47(13) . . ?
N5 Fe2 N4 75.42(13) . . ?
Fe1 O1 Fe2 102.61(12) . . ?
C1 O1 Fe1 127.7(2) . . ?
C1 O1 Fe2 115.8(2) . . ?
Fe1 O2 Fe2 102.45(12) . . ?
C11 O2 Fe1 130.8(2) . . ?
C11 O2 Fe2 115.8(2) . . ?
O10 O10 O10 60.000(4) 4_664 5_566 ?
O11 O10 O10 96.9(12) 5_566 5_566 ?
O11 O10 O10 114.6(9) 5_566 4_664 ?
O11 O10 N9 57.2(8) 5_566 . ?
N9 O10 O10 59.0(6) . 4_664 ?
N9 O10 O10 59.0(6) . 5_566 ?
O10 O11 O12 105.0(11) 4_664 4_664 ?
O12 O11 O10 123.0(15) 5_566 4_664 ?
O12 O11 O12 61.1(11) 5_566 4_664 ?
O12 O11 N9 70.2(10) 5_566 . ?
N9 O11 O10 64.9(9) . 4_664 ?
N9 O11 O12 46.3(7) . 4_664 ?
O11 O12 O11 91.8(13) 4_664 5_566 ?
O11 O12 O12 84.1(11) 4_664 5_566 ?
O11 O12 O12 113.9(9) 4_664 4_664 ?
O11 O12 N9 61.5(9) 4_664 . ?
O12 O12 O11 34.8(6) 4_664 5_566 ?
O12 O12 O11 81.5(6) 5_566 5_566 ?
O12 O12 O12 60.003(2) 4_664 5_566 ?
N9 O12 O11 42.5(5) . 5_566 ?
N9 O12 O12 52.5(5) . 4_664 ?
N9 O12 O12 52.5(5) . 5_566 ?
C6 N1 Fe2 115.8(3) . . ?
C7 N1 Fe2 117.8(3) . . ?
C7 N1 C6 126.3(4) . . ?
C8 N2 Fe2 113.3(3) . . ?
C8 N2 C10 105.2(4) . . ?
C10 N2 Fe2 141.5(3) . . ?
C8 N3 C9 106.5(4) . . ?
C8 N3 H3 127(3) . . ?
C9 N3 H3 126(3) . . ?
C16 N4 Fe2 116.2(3) . . ?
C17 N4 Fe2 117.7(3) . . ?
C17 N4 C16 126.1(4) . . ?
C18 N5 Fe2 111.9(3) . . ?
C18 N5 C20 105.8(4) . . ?
C20 N5 Fe2 142.3(3) . . ?
C18 N6 C19 107.8(4) . . ?
C18 N6 H6 126(4) . . ?
C19 N6 H6 126(4) . . ?
O8 N7 O8 119.994(5) 5_566 . ?
O8 N7 O8 119.998(5) 4_664 5_566 ?
O8 N7 O8 120.001(5) 4_664 . ?
O9 N8 O9 120.002(1) . 6_655 ?
O9 N8 O9 119.999(1) . 7_564 ?
O9 N8 O9 120.000(1) 6_655 7_564 ?
O10 N9 O10 62.0(11) 5_566 . ?
O10 N9 O10 62.0(11) 4_664 5_566 ?
O10 N9 O10 62.0(11) 4_664 . ?
O11 N9 O10 118.2(12) 5_566 4_664 ?
O11 N9 O10 57.9(9) 5_566 . ?
O11 N9 O10 99.6(11) 4_664 4_664 ?
O11 N9 O10 99.5(11) . . ?
O11 N9 O10 118.2(12) . 5_566 ?
O11 N9 O10 118.2(12) 4_664 . ?
O11 N9 O10 99.6(11) 5_566 5_566 ?
O11 N9 O10 57.9(9) 4_664 5_566 ?
O11 N9 O10 57.9(9) . 4_664 ?
O11 N9 O11 119.80(13) . 4_664 ?
O11 N9 O11 119.80(13) 5_566 4_664 ?
O11 N9 O11 119.80(13) . 5_566 ?
O11 N9 O12 91.2(10) 4_664 5_566 ?
O11 N9 O12 48.3(7) 5_566 4_664 ?
O11 N9 O12 123.2(11) . . ?
O11 N9 O12 91.2(10) . 4_664 ?
O11 N9 O12 91.2(10) 5_566 . ?
O11 N9 O12 123.2(11) 4_664 4_664 ?
O11 N9 O12 48.3(7) 4_664 . ?
O11 N9 O12 123.2(11) 5_566 5_566 ?
O11 N9 O12 48.3(7) . 5_566 ?
O12 N9 O10 99.1(8) . 5_566 ?
O12 N9 O10 99.1(8) 5_566 4_664 ?
O12 N9 O10 146.2(9) 5_566 . ?
O12 N9 O10 136.6(9) 5_566 5_566 ?
O12 N9 O10 136.6(9) 4_664 4_664 ?
O12 N9 O10 146.2(9) 4_664 5_566 ?
O12 N9 O10 99.1(8) 4_664 . ?
O12 N9 O10 146.2(9) . 4_664 ?
O12 N9 O10 136.6(9) . . ?
O12 N9 O12 75.0(9) 5_566 4_664 ?
O12 N9 O12 75.0(9) . 4_664 ?
O12 N9 O12 75.0(9) . 5_566 ?
O1 C1 C2 122.6(4) . . ?
O1 C1 C6 117.5(4) . . ?
C2 C1 C6 119.9(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(5) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 C2 120.6(5) . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.7(5) . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C1 113.2(4) . . ?
N1 C6 C5 127.2(4) . . ?
C5 C6 C1 119.6(4) . . ?
N1 C7 H7 123.3 . . ?
N1 C7 C8 113.4(4) . . ?
C8 C7 H7 123.3 . . ?
N2 C8 N3 111.9(4) . . ?
N2 C8 C7 120.6(4) . . ?
N3 C8 C7 127.4(4) . . ?
N3 C9 H9 126.8 . . ?
N3 C9 C10 106.4(4) . . ?
C10 C9 H9 126.8 . . ?
N2 C10 C9 110.1(4) . . ?
N2 C10 H10 125.0 . . ?
C9 C10 H10 125.0 . . ?
O2 C11 C12 122.7(4) . . ?
O2 C11 C16 118.3(4) . . ?
C12 C11 C16 119.0(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.5(4) . . ?
C16 C15 H15 119.8 . . ?
N4 C16 C11 112.2(3) . . ?
C15 C16 N4 127.5(4) . . ?
C15 C16 C11 120.3(4) . . ?
N4 C17 H17 123.0 . . ?
N4 C17 C18 114.0(4) . . ?
C18 C17 H17 123.0 . . ?
N5 C18 N6 110.9(4) . . ?
N5 C18 C17 120.5(4) . . ?
N6 C18 C17 128.4(4) . . ?
N6 C19 H19 127.0 . . ?
N6 C19 C20 105.9(4) . . ?
C20 C19 H19 127.0 . . ?
N5 C20 C19 109.5(4) . . ?
N5 C20 H20 125.2 . . ?
C19 C20 H20 125.2 . . ?

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
N3 H3 O9 0.903(19) 2.00(2) 2.873(5) 162(4) .
N6 H6 O8 0.900(19) 1.93(2) 2.825(5) 172(5) .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_542p-1
_database_code_depnum_ccdc_archive 'CCDC 1830690'
_audit_update_record             
;
2018-04-18 deposited with the CCDC.
2018-04-30 downloaded from the CCDC.
;
_audit_creation_date             2018-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Fe N6 O2, N O3, C0.7 H2.8 O0.7'
_chemical_formula_sum            'C20.70 H18.80 Fe N7 O5.70'
_chemical_formula_weight         512.68
_chemical_melting_point          ?
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'
Fe Fe 0.3463 0.8444 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0937(7)
_cell_length_b                   11.1693(9)
_cell_length_c                   11.2944(10)
_cell_angle_alpha                96.510(4)
_cell_angle_beta                 104.934(4)
_cell_angle_gamma                97.485(3)
_cell_volume                     1085.98(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5111
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.61
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.807
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/3 (Bruker AXS, 2014)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             527
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.004
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13639
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.997
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.576
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker APEX2 V2.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3076
_reflns_number_total             3909
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker Apex2 V2.0'
_computing_data_collection       'Bruker Apex2 V2.0'
_computing_data_reduction        'Bruker Apex2 V2.0'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3909
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.7181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 O6A-C21 \\sim O6B-C21
 with sigma of 0.004
3. Others
 Fixed Sof: O6B(0.25) H6B(0.25) C21(0.7) H21D(0.25) H21E(0.25) H21F(0.25)
 H21A(0.45) H21B(0.45) H21C(0.45) O6A(0.45) H6A(0.45)
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), C1(H1), C2(H2A), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20)
4.b Idealised Me refined as rotating group:
 C21(H21D,H21E,H21F), C21(H21A,H21B,H21C)
4.c Idealised tetrahedral OH refined as rotating group:
 O6B(H6B), O6A(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.45849(4) 0.51684(3) 0.23541(4) 0.02222(13) Uani 1 1 d . . . . .
O1 O 0.65366(18) 0.62171(15) 0.32475(18) 0.0264(4) Uani 1 1 d . . . . .
O2 O 0.54805(19) 0.36972(15) 0.21648(18) 0.0278(4) Uani 1 1 d . . . . .
O3 O 0.92488(19) 0.39728(16) 0.33274(19) 0.0304(5) Uani 1 1 d . . . . .
O4 O 0.9187(2) 0.25842(18) 0.1804(2) 0.0450(6) Uani 1 1 d . . . . .
O5 O 0.9641(2) 0.21568(17) 0.3677(2) 0.0392(5) Uani 1 1 d . . . . .
O6B O 0.7227(13) 0.0934(15) -0.079(2) 0.080(6) Uani 0.25 1 d D . P A 2
H6B H 0.643353 0.043849 -0.119814 0.120 Uiso 0.25 1 calc GR . P A 2
N1 N 0.2663(2) 0.45595(18) 0.0722(2) 0.0249(5) Uani 1 1 d . . . . .
N2 N 0.1444(2) 0.4856(2) -0.1157(2) 0.0303(5) Uani 1 1 d . . . . .
H2 H 0.119685 0.519351 -0.183339 0.036 Uiso 1 1 calc R . . . .
N3 N 0.4794(2) 0.64819(18) 0.1137(2) 0.0232(5) Uani 1 1 d . . . . .
N4 N 0.3271(2) 0.62875(17) 0.3227(2) 0.0227(5) Uani 1 1 d . . . . .
N5 N 0.1970(2) 0.65184(18) 0.4608(2) 0.0235(5) Uani 1 1 d . . . . .
H5 H 0.148313 0.635036 0.516398 0.028 Uiso 1 1 calc R . . . .
N6 N 0.3638(2) 0.40591(17) 0.3503(2) 0.0202(5) Uani 1 1 d . . . . .
N7 N 0.9368(2) 0.2885(2) 0.2932(2) 0.0283(5) Uani 1 1 d . . . . .
C1 C 0.1480(3) 0.3602(2) 0.0209(3) 0.0288(6) Uani 1 1 d . . . . .
H1 H 0.122614 0.292355 0.059763 0.035 Uiso 1 1 calc R . . . .
C2 C 0.0724(3) 0.3783(2) -0.0953(3) 0.0324(7) Uani 1 1 d . . . . .
H2A H -0.014141 0.325801 -0.151404 0.039 Uiso 1 1 calc R . . . .
C3 C 0.2604(3) 0.5304(2) -0.0130(3) 0.0244(6) Uani 1 1 d . . . . .
C4 C 0.3724(3) 0.6403(2) 0.0120(3) 0.0265(6) Uani 1 1 d . . . . .
H4 H 0.367815 0.700693 -0.041130 0.032 Uiso 1 1 calc R . . . .
C5 C 0.6046(3) 0.7430(2) 0.1656(3) 0.0244(6) Uani 1 1 d . . . . .
C6 C 0.6944(3) 0.7225(2) 0.2805(3) 0.0249(6) Uani 1 1 d . . . . .
C7 C 0.8257(3) 0.8092(2) 0.3443(3) 0.0303(7) Uani 1 1 d . . . . .
H7 H 0.888525 0.797744 0.422273 0.036 Uiso 1 1 calc R . . . .
C8 C 0.8622(3) 0.9114(2) 0.2919(3) 0.0338(7) Uani 1 1 d . . . . .
H8 H 0.950319 0.970215 0.335438 0.041 Uiso 1 1 calc R . . . .
C9 C 0.7739(3) 0.9302(2) 0.1779(3) 0.0340(7) Uani 1 1 d . . . . .
H9 H 0.802398 1.000910 0.144077 0.041 Uiso 1 1 calc R . . . .
C10 C 0.6443(3) 0.8463(2) 0.1134(3) 0.0301(7) Uani 1 1 d . . . . .
H10 H 0.583349 0.858416 0.035033 0.036 Uiso 1 1 calc R . . . .
C11 C 0.2983(3) 0.7462(2) 0.3343(3) 0.0295(7) Uani 1 1 d . . . . .
H11 H 0.329684 0.807665 0.290061 0.035 Uiso 1 1 calc R . . . .
C12 C 0.2174(3) 0.7609(2) 0.4195(3) 0.0280(6) Uani 1 1 d . . . . .
H12 H 0.182131 0.833243 0.445164 0.034 Uiso 1 1 calc R . . . .
C13 C 0.2650(3) 0.5744(2) 0.4010(2) 0.0196(5) Uani 1 1 d . . . . .
C14 C 0.2810(3) 0.4503(2) 0.4155(2) 0.0205(6) Uani 1 1 d . . . . .
H14 H 0.235385 0.405793 0.467573 0.025 Uiso 1 1 calc R . . . .
C15 C 0.4025(3) 0.2881(2) 0.3422(3) 0.0216(6) Uani 1 1 d . . . . .
C16 C 0.5038(3) 0.2750(2) 0.2676(3) 0.0214(6) Uani 1 1 d . . . . .
C17 C 0.5558(3) 0.1630(2) 0.2538(3) 0.0268(6) Uani 1 1 d . . . . .
H17 H 0.624634 0.151407 0.204593 0.032 Uiso 1 1 calc R . . . .
C18 C 0.5068(3) 0.0698(2) 0.3119(3) 0.0353(7) Uani 1 1 d . . . . .
H18 H 0.542921 -0.005806 0.302347 0.042 Uiso 1 1 calc R . . . .
C19 C 0.4058(4) 0.0840(2) 0.3841(3) 0.0407(8) Uani 1 1 d . . . . .
H19 H 0.372734 0.018016 0.422402 0.049 Uiso 1 1 calc R . . . .
C20 C 0.3536(3) 0.1930(2) 0.4004(3) 0.0306(7) Uani 1 1 d . . . . .
H20 H 0.285360 0.203438 0.450486 0.037 Uiso 1 1 calc R . . . .
C21 C 0.8529(6) 0.0490(5) -0.0955(6) 0.0689(16) Uani 0.7 1 d D . P . .
H21D H 0.844046 0.031390 -0.184273 0.103 Uiso 0.25 1 calc GR . P A 2
H21E H 0.861704 -0.026079 -0.058827 0.103 Uiso 0.25 1 calc GR . P A 2
H21F H 0.944798 0.110325 -0.054828 0.103 Uiso 0.25 1 calc GR . P A 2
H21A H 0.859537 0.055651 -0.179792 0.103 Uiso 0.45 1 calc GR . P A 1
H21B H 0.794539 -0.031021 -0.094836 0.103 Uiso 0.45 1 calc GR . P A 1
H21C H 0.957050 0.057842 -0.039432 0.103 Uiso 0.45 1 calc GR . P A 1
O6A O 0.7787(9) 0.1402(8) -0.0565(14) 0.073(3) Uani 0.45 1 d D . P A 1
H6A H 0.830708 0.176229 0.014161 0.109 Uiso 0.45 1 calc GR . P A 1


_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 O1 1.9513(17) . ?
Fe1 O2 1.9412(16) . ?
Fe1 N1 2.159(2) . ?
Fe1 N3 2.144(2) . ?
Fe1 N4 2.1630(19) . ?
Fe1 N6 2.150(2) . ?
O1 C6 1.330(3) . ?
O2 C16 1.328(3) . ?
O3 N7 1.274(3) . ?
O4 N7 1.243(3) . ?
O5 N7 1.237(3) . ?
O6B H6B 0.8400 . ?
O6B C21 1.387(7) . ?
N1 C1 1.369(3) . ?
N1 C3 1.337(3) . ?
N2 H2 0.8800 . ?
N2 C2 1.362(3) . ?
N2 C3 1.345(4) . ?
N3 C4 1.285(3) . ?
N3 C5 1.401(3) . ?
N4 C11 1.370(3) . ?
N4 C13 1.326(3) . ?
N5 H5 0.8800 . ?
N5 C12 1.360(3) . ?
N5 C13 1.345(3) . ?
N6 C14 1.287(3) . ?
N6 C15 1.405(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.367(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.440(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(4) . ?
C5 C10 1.401(4) . ?
C6 C7 1.407(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.361(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.436(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.409(3) . ?
C15 C20 1.394(4) . ?
C16 C17 1.400(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.374(4) . ?
C20 H20 0.9500 . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 O6A 1.384(7) . ?
O6A H6A 0.8400 . ?

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
O1 Fe1 N1 151.86(8) . . ?
O1 Fe1 N3 77.66(8) . . ?
O1 Fe1 N4 92.48(7) . . ?
O1 Fe1 N6 113.20(8) . . ?
O2 Fe1 O1 95.10(7) . . ?
O2 Fe1 N1 93.87(8) . . ?
O2 Fe1 N3 118.70(8) . . ?
O2 Fe1 N4 151.36(8) . . ?
O2 Fe1 N6 77.60(7) . . ?
N1 Fe1 N4 92.29(8) . . ?
N3 Fe1 N1 74.64(8) . . ?
N3 Fe1 N4 89.90(8) . . ?
N3 Fe1 N6 160.56(7) . . ?
N6 Fe1 N1 94.76(8) . . ?
N6 Fe1 N4 74.03(7) . . ?
C6 O1 Fe1 118.16(17) . . ?
C16 O2 Fe1 119.06(14) . . ?
C21 O6B H6B 109.5 . . ?
C1 N1 Fe1 140.99(19) . . ?
C3 N1 Fe1 113.00(17) . . ?
C3 N1 C1 105.9(2) . . ?
C2 N2 H2 126.5 . . ?
C3 N2 H2 126.5 . . ?
C3 N2 C2 107.1(2) . . ?
C4 N3 Fe1 119.16(17) . . ?
C4 N3 C5 127.6(2) . . ?
C5 N3 Fe1 112.79(17) . . ?
C11 N4 Fe1 140.06(18) . . ?
C13 N4 Fe1 113.49(15) . . ?
C13 N4 C11 106.0(2) . . ?
C12 N5 H5 126.3 . . ?
C13 N5 H5 126.3 . . ?
C13 N5 C12 107.4(2) . . ?
C14 N6 Fe1 119.69(16) . . ?
C14 N6 C15 127.7(2) . . ?
C15 N6 Fe1 112.62(15) . . ?
O4 N7 O3 118.8(2) . . ?
O5 N7 O3 119.3(2) . . ?
O5 N7 O4 121.9(2) . . ?
N1 C1 H1 125.6 . . ?
C2 C1 N1 108.9(2) . . ?
C2 C1 H1 125.6 . . ?
N2 C2 C1 107.1(3) . . ?
N2 C2 H2A 126.4 . . ?
C1 C2 H2A 126.4 . . ?
N1 C3 N2 111.1(2) . . ?
N1 C3 C4 119.8(2) . . ?
N2 C3 C4 129.1(3) . . ?
N3 C4 C3 112.9(2) . . ?
N3 C4 H4 123.5 . . ?
C3 C4 H4 123.5 . . ?
N3 C5 C6 111.6(2) . . ?
N3 C5 C10 126.9(3) . . ?
C10 C5 C6 121.5(2) . . ?
O1 C6 C5 119.1(2) . . ?
O1 C6 C7 122.2(3) . . ?
C5 C6 C7 118.6(2) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 119.0 . . ?
C7 C8 C9 121.9(3) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 120.6 . . ?
C9 C10 C5 118.8(3) . . ?
C9 C10 H10 120.6 . . ?
N4 C11 H11 125.5 . . ?
C12 C11 N4 109.1(2) . . ?
C12 C11 H11 125.5 . . ?
N5 C12 C11 106.7(2) . . ?
N5 C12 H12 126.7 . . ?
C11 C12 H12 126.7 . . ?
N4 C13 N5 110.9(2) . . ?
N4 C13 C14 120.1(2) . . ?
N5 C13 C14 129.0(2) . . ?
N6 C14 C13 112.6(2) . . ?
N6 C14 H14 123.7 . . ?
C13 C14 H14 123.7 . . ?
N6 C15 C16 111.6(2) . . ?
C20 C15 N6 126.7(2) . . ?
C20 C15 C16 121.7(2) . . ?
O2 C16 C15 118.7(2) . . ?
O2 C16 C17 123.2(2) . . ?
C17 C16 C15 118.0(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 120.6 . . ?
C19 C20 C15 118.8(2) . . ?
C19 C20 H20 120.6 . . ?
O6B C21 H21D 109.5 . . ?
O6B C21 H21E 109.5 . . ?
O6B C21 H21F 109.5 . . ?
H21D C21 H21E 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6A C21 H21A 109.5 . . ?
O6A C21 H21B 109.5 . . ?
O6A C21 H21C 109.5 . . ?
C21 O6A H6A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C6 C5 -6.6(3) . . . . ?
Fe1 O1 C6 C7 174.20(17) . . . . ?
Fe1 O2 C16 C15 -5.0(3) . . . . ?
Fe1 O2 C16 C17 176.7(2) . . . . ?
Fe1 N1 C1 C2 -175.18(19) . . . . ?
Fe1 N1 C3 N2 176.54(15) . . . . ?
Fe1 N1 C3 C4 -2.3(3) . . . . ?
Fe1 N3 C4 C3 -8.0(3) . . . . ?
Fe1 N3 C5 C6 5.4(2) . . . . ?
Fe1 N3 C5 C10 -175.94(19) . . . . ?
Fe1 N4 C11 C12 -171.6(2) . . . . ?
Fe1 N4 C13 N5 174.33(16) . . . . ?
Fe1 N4 C13 C14 -3.5(3) . . . . ?
Fe1 N6 C14 C13 -0.5(3) . . . . ?
Fe1 N6 C15 C16 4.4(3) . . . . ?
Fe1 N6 C15 C20 -176.9(2) . . . . ?
O1 C6 C7 C8 179.2(2) . . . . ?
O2 C16 C17 C18 178.7(3) . . . . ?
N1 C1 C2 N2 0.0(3) . . . . ?
N1 C3 C4 N3 6.7(3) . . . . ?
N2 C3 C4 N3 -171.8(2) . . . . ?
N3 C5 C6 O1 0.2(3) . . . . ?
N3 C5 C6 C7 179.4(2) . . . . ?
N3 C5 C10 C9 -179.3(2) . . . . ?
N4 C11 C12 N5 0.2(3) . . . . ?
N4 C13 C14 N6 2.7(3) . . . . ?
N5 C13 C14 N6 -174.7(2) . . . . ?
N6 C15 C16 O2 -0.1(3) . . . . ?
N6 C15 C16 C17 178.3(2) . . . . ?
N6 C15 C20 C19 -178.6(3) . . . . ?
C1 N1 C3 N2 -0.3(3) . . . . ?
C1 N1 C3 C4 -179.1(2) . . . . ?
C2 N2 C3 N1 0.3(3) . . . . ?
C2 N2 C3 C4 178.9(2) . . . . ?
C3 N1 C1 C2 0.2(3) . . . . ?
C3 N2 C2 C1 -0.2(3) . . . . ?
C4 N3 C5 C6 177.5(2) . . . . ?
C4 N3 C5 C10 -3.9(4) . . . . ?
C5 N3 C4 C3 -179.5(2) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C5 C10 C9 -0.8(4) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 C5 0.2(4) . . . . ?
C10 C5 C6 O1 -178.5(2) . . . . ?
C10 C5 C6 C7 0.7(3) . . . . ?
C11 N4 C13 N5 0.6(3) . . . . ?
C11 N4 C13 C14 -177.3(2) . . . . ?
C12 N5 C13 N4 -0.4(3) . . . . ?
C12 N5 C13 C14 177.2(3) . . . . ?
C13 N4 C11 C12 -0.5(3) . . . . ?
C13 N5 C12 C11 0.1(3) . . . . ?
C14 N6 C15 C16 -176.1(2) . . . . ?
C14 N6 C15 C20 2.6(4) . . . . ?
C15 N6 C14 C13 -179.9(2) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C15 C20 C19 -0.1(4) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
C18 C19 C20 C15 0.7(5) . . . . ?
C20 C15 C16 O2 -178.9(2) . . . . ?
C20 C15 C16 C17 -0.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
