# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_GNDU010
_database_code_depnum_ccdc_archive 'CCDC 1499222'
_audit_update_record             
;
2016-08-15 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 Fe O4'
_chemical_formula_weight         386.17

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'
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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.8948(12)
_cell_length_b                   6.6730(6)
_cell_length_c                   15.6759(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.464(9)
_cell_angle_gamma                90
_cell_volume                     1635.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2072
_cell_measurement_theta_min      3.6510
_cell_measurement_theta_max      22.7720

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.947
_shelx_estimated_absorpt_T_min   0.745
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_T_min  0.63460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            11188
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_av_R_equivalents  0.1174
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.152
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2874
_reflns_number_gt                1791
_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.1500P)²+0.0723P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.060(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1425
_refine_ls_R_factor_gt           0.0970
_refine_ls_wR_factor_ref         0.2883
_refine_ls_wR_factor_gt          0.2277
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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
Fe1 Fe 0.13384(6) 0.26424(15) 0.42972(7) 0.0610(6) Uani 1 1 d . . . . .
O1 O 0.7515(4) 0.1356(10) 0.2800(5) 0.098(2) Uani 1 1 d . . . . .
O2 O 0.6301(3) 0.1541(7) 0.3326(3) 0.0605(13) Uani 1 1 d . . . . .
O3 O 0.4320(3) 0.7866(6) 0.3878(4) 0.0585(14) Uani 1 1 d . . . . .
O4 O 0.3130(4) 0.8120(7) 0.4432(4) 0.0762(17) Uani 1 1 d . . . . .
C1 C 0.6978(5) 0.2380(11) 0.2975(6) 0.066(2) Uani 1 1 d . . . . .
C2 C 0.6841(4) 0.4605(11) 0.2908(5) 0.0580(18) Uani 1 1 d . . . . .
H2A H 0.7324 0.5333 0.3263 0.070 Uiso 1 1 calc R U . . .
H2B H 0.6776 0.5058 0.2299 0.070 Uiso 1 1 calc R U . . .
C3 C 0.6041(4) 0.4923(9) 0.3248(4) 0.0504(16) Uani 1 1 d . . . . .
C4 C 0.5756(4) 0.3084(8) 0.3486(4) 0.0457(15) Uani 1 1 d . . . . .
C5 C 0.5581(4) 0.6642(9) 0.3367(4) 0.0524(16) Uani 1 1 d . . . . .
H5 H 0.5759 0.7939 0.3224 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4852(4) 0.6337(8) 0.3704(4) 0.0489(16) Uani 1 1 d . . . . .
C7 C 0.4554(4) 0.4473(8) 0.3930(4) 0.0437(14) Uani 1 1 d . . . . .
C8 C 0.5027(4) 0.2749(8) 0.3825(4) 0.0465(15) Uani 1 1 d . . . . .
H8 H 0.4859 0.1450 0.3976 0.056 Uiso 1 1 calc R U . . .
C9 C 0.3774(4) 0.4833(8) 0.4268(4) 0.0452(15) Uani 1 1 d . . . . .
C10 C 0.3650(5) 0.7051(9) 0.4234(5) 0.0550(18) Uani 1 1 d . . . . .
C11 C 0.2515(4) 0.3589(9) 0.4933(4) 0.0511(16) Uani 1 1 d . . . . .
C12 C 0.3280(4) 0.3417(9) 0.4570(4) 0.0445(15) Uani 1 1 d . . . . .
H12 H 0.3477 0.2082 0.4533 0.053 Uiso 1 1 calc R U . . .
C13 C 0.1892(4) 0.5152(11) 0.4907(5) 0.066(2) Uani 1 1 d . . . . .
H13 H 0.1912 0.6438 0.4652 0.079 Uiso 1 1 calc R U . . .
C14 C 0.1242(4) 0.4424(15) 0.5332(6) 0.081(3) Uani 1 1 d . . . . .
H14 H 0.0749 0.5154 0.5413 0.097 Uiso 1 1 calc R U . . .
C15 C 0.1437(5) 0.2454(12) 0.5616(6) 0.066(2) Uani 1 1 d . . . . .
H15 H 0.1104 0.1642 0.5925 0.079 Uiso 1 1 calc R U . . .
C16 C 0.2207(4) 0.1885(11) 0.5365(5) 0.0550(17) Uani 1 1 d . . . . .
H16 H 0.2479 0.0616 0.5462 0.066 Uiso 1 1 calc R U . . .
C17 C 0.1335(8) 0.2435(15) 0.3007(6) 0.091(3) Uani 1 1 d . . . . .
H17 H 0.1746 0.3007 0.2708 0.109 Uiso 1 1 calc R U . . .
C18 C 0.0546(12) 0.3415(17) 0.3197(9) 0.150(7) Uani 1 1 d . . . . .
H18 H 0.0348 0.4743 0.3068 0.181 Uiso 1 1 calc R U . . .
C19 C 0.0176(6) 0.190(2) 0.3608(9) 0.122(5) Uani 1 1 d . . . . .
H19 H -0.0359 0.2044 0.3791 0.146 Uiso 1 1 calc R U . . .
C20 C 0.0640(6) 0.0234(17) 0.3722(7) 0.106(3) Uani 1 1 d . . . . .
H20 H 0.0507 -0.0950 0.4007 0.127 Uiso 1 1 calc R U . . .
C21 C 0.1347(5) 0.0545(16) 0.3349(5) 0.080(3) Uani 1 1 d . . . . .
H21 H 0.1784 -0.0417 0.3331 0.096 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 C18 2.009(9) . ?
Fe1 C19 2.025(9) . ?
Fe1 C17 2.027(10) . ?
Fe1 C16 2.032(7) . ?
Fe1 C14 2.039(8) . ?
Fe1 C21 2.043(8) . ?
Fe1 C13 2.046(7) . ?
Fe1 C15 2.048(9) . ?
Fe1 C11 2.052(6) . ?
Fe1 C20 2.066(9) . ?
O1 C1 1.164(9) . ?
O2 C4 1.397(7) . ?
O2 C1 1.410(9) . ?
O3 C6 1.384(7) . ?
O3 C10 1.399(9) . ?
O4 C10 1.175(8) . ?
C1 C2 1.501(10) . ?
C2 C3 1.481(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.382(8) . ?
C3 C5 1.390(9) . ?
C4 C8 1.377(9) . ?
C5 C6 1.374(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(8) . ?
C7 C8 1.400(8) . ?
C7 C9 1.454(8) . ?
C8 H8 0.9500 . ?
C9 C12 1.367(8) . ?
C9 C10 1.493(8) . ?
C11 C13 1.434(9) . ?
C11 C12 1.438(8) . ?
C11 C16 1.453(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.413(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.405(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.404(10) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C21 1.369(13) . ?
C17 C18 1.49(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.330(14) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(11) . ?
C20 H20 0.9500 . ?
C21 H21 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
C18 Fe1 C19 40.2(6) . . ?
C18 Fe1 C17 43.3(6) . . ?
C19 Fe1 C17 67.3(5) . . ?
C18 Fe1 C16 176.1(7) . . ?
C19 Fe1 C16 142.9(6) . . ?
C17 Fe1 C16 133.2(4) . . ?
C18 Fe1 C14 114.0(5) . . ?
C19 Fe1 C14 111.9(4) . . ?
C17 Fe1 C14 147.9(4) . . ?
C16 Fe1 C14 68.1(3) . . ?
C18 Fe1 C21 68.7(4) . . ?
C19 Fe1 C21 64.6(3) . . ?
C17 Fe1 C21 39.3(3) . . ?
C16 Fe1 C21 109.6(3) . . ?
C14 Fe1 C21 171.6(4) . . ?
C18 Fe1 C13 109.9(4) . . ?
C19 Fe1 C13 136.2(4) . . ?
C17 Fe1 C13 116.5(4) . . ?
C16 Fe1 C13 69.4(3) . . ?
C14 Fe1 C13 40.5(3) . . ?
C21 Fe1 C13 147.3(3) . . ?
C18 Fe1 C15 143.4(7) . . ?
C19 Fe1 C15 114.7(5) . . ?
C17 Fe1 C15 171.5(4) . . ?
C16 Fe1 C15 40.3(3) . . ?
C14 Fe1 C15 40.2(3) . . ?
C21 Fe1 C15 133.0(4) . . ?
C13 Fe1 C15 68.4(3) . . ?
C18 Fe1 C11 135.3(6) . . ?
C19 Fe1 C11 175.4(5) . . ?
C17 Fe1 C11 110.1(4) . . ?
C16 Fe1 C11 41.7(3) . . ?
C14 Fe1 C11 68.2(3) . . ?
C21 Fe1 C11 116.0(3) . . ?
C13 Fe1 C11 40.9(2) . . ?
C15 Fe1 C11 68.5(3) . . ?
C18 Fe1 C20 67.8(5) . . ?
C19 Fe1 C20 37.9(4) . . ?
C17 Fe1 C20 66.9(4) . . ?
C16 Fe1 C20 113.4(4) . . ?
C14 Fe1 C20 133.5(4) . . ?
C21 Fe1 C20 39.1(3) . . ?
C13 Fe1 C20 172.9(3) . . ?
C15 Fe1 C20 109.2(4) . . ?
C11 Fe1 C20 145.3(4) . . ?
C4 O2 C1 108.6(5) . . ?
C6 O3 C10 109.2(4) . . ?
O1 C1 O2 120.2(7) . . ?
O1 C1 C2 131.9(7) . . ?
O2 C1 C2 108.0(6) . . ?
C3 C2 C1 103.9(5) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C5 119.4(6) . . ?
C4 C3 C2 108.3(6) . . ?
C5 C3 C2 132.3(6) . . ?
C8 C4 C3 125.9(6) . . ?
C8 C4 O2 122.8(5) . . ?
C3 C4 O2 111.2(5) . . ?
C6 C5 C3 115.4(6) . . ?
C6 C5 H5 122.3 . . ?
C3 C5 H5 122.3 . . ?
C5 C6 O3 123.8(5) . . ?
C5 C6 C7 125.2(6) . . ?
O3 C6 C7 111.0(6) . . ?
C6 C7 C8 119.1(5) . . ?
C6 C7 C9 107.2(5) . . ?
C8 C7 C9 133.6(5) . . ?
C4 C8 C7 114.8(5) . . ?
C4 C8 H8 122.6 . . ?
C7 C8 H8 122.6 . . ?
C12 C9 C7 126.4(5) . . ?
C12 C9 C10 128.1(6) . . ?
C7 C9 C10 105.5(5) . . ?
O4 C10 O3 119.5(6) . . ?
O4 C10 C9 133.4(7) . . ?
O3 C10 C9 107.1(5) . . ?
C13 C11 C12 132.6(6) . . ?
C13 C11 C16 107.0(6) . . ?
C12 C11 C16 120.2(6) . . ?
C13 C11 Fe1 69.3(4) . . ?
C12 C11 Fe1 123.0(5) . . ?
C16 C11 Fe1 68.4(3) . . ?
C9 C12 C11 131.5(6) . . ?
C9 C12 H12 114.2 . . ?
C11 C12 H12 114.2 . . ?
C14 C13 C11 107.3(7) . . ?
C14 C13 Fe1 69.5(4) . . ?
C11 C13 Fe1 69.8(4) . . ?
C14 C13 H13 126.3 . . ?
C11 C13 H13 126.3 . . ?
Fe1 C13 H13 126.0 . . ?
C15 C14 C13 109.4(7) . . ?
C15 C14 Fe1 70.2(5) . . ?
C13 C14 Fe1 70.0(4) . . ?
C15 C14 H14 125.3 . . ?
C13 C14 H14 125.3 . . ?
Fe1 C14 H14 126.0 . . ?
C16 C15 C14 108.5(7) . . ?
C16 C15 Fe1 69.2(5) . . ?
C14 C15 Fe1 69.6(5) . . ?
C16 C15 H15 125.7 . . ?
C14 C15 H15 125.7 . . ?
Fe1 C15 H15 127.1 . . ?
C15 C16 C11 107.7(6) . . ?
C15 C16 Fe1 70.5(5) . . ?
C11 C16 Fe1 69.9(4) . . ?
C15 C16 H16 126.2 . . ?
C11 C16 H16 126.2 . . ?
Fe1 C16 H16 125.0 . . ?
C21 C17 C18 106.1(11) . . ?
C21 C17 Fe1 71.0(6) . . ?
C18 C17 Fe1 67.7(6) . . ?
C21 C17 H17 126.9 . . ?
C18 C17 H17 126.9 . . ?
Fe1 C17 H17 125.9 . . ?
C19 C18 C17 102.6(8) . . ?
C19 C18 Fe1 70.5(6) . . ?
C17 C18 Fe1 69.0(6) . . ?
C19 C18 H18 128.7 . . ?
C17 C18 H18 128.7 . . ?
Fe1 C18 H18 123.6 . . ?
C20 C19 C18 113.6(12) . . ?
C20 C19 Fe1 72.7(5) . . ?
C18 C19 Fe1 69.3(6) . . ?
C20 C19 H19 123.2 . . ?
C18 C19 H19 123.2 . . ?
Fe1 C19 H19 126.5 . . ?
C19 C20 C21 107.0(12) . . ?
C19 C20 Fe1 69.4(6) . . ?
C21 C20 Fe1 69.6(5) . . ?
C19 C20 H20 126.5 . . ?
C21 C20 H20 126.5 . . ?
Fe1 C20 H20 126.1 . . ?
C17 C21 C20 110.6(10) . . ?
C17 C21 Fe1 69.7(6) . . ?
C20 C21 Fe1 71.3(5) . . ?
C17 C21 H21 124.7 . . ?
C20 C21 H21 124.7 . . ?
Fe1 C21 H21 125.9 . . ?

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 O2 C1 O1 179.3(8) . . . . ?
C4 O2 C1 C2 -0.3(8) . . . . ?
O1 C1 C2 C3 -179.5(10) . . . . ?
O2 C1 C2 C3 0.0(8) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
C1 C2 C3 C5 179.2(8) . . . . ?
C5 C3 C4 C8 1.5(11) . . . . ?
C2 C3 C4 C8 -179.5(7) . . . . ?
C5 C3 C4 O2 -179.5(6) . . . . ?
C2 C3 C4 O2 -0.4(8) . . . . ?
C1 O2 C4 C8 179.5(7) . . . . ?
C1 O2 C4 C3 0.5(8) . . . . ?
C4 C3 C5 C6 -1.3(10) . . . . ?
C2 C3 C5 C6 179.9(7) . . . . ?
C3 C5 C6 O3 179.0(6) . . . . ?
C3 C5 C6 C7 0.2(10) . . . . ?
C10 O3 C6 C5 -178.6(6) . . . . ?
C10 O3 C6 C7 0.4(8) . . . . ?
C5 C6 C7 C8 1.0(10) . . . . ?
O3 C6 C7 C8 -178.0(6) . . . . ?
C5 C6 C7 C9 179.3(6) . . . . ?
O3 C6 C7 C9 0.4(7) . . . . ?
C3 C4 C8 C7 -0.3(10) . . . . ?
O2 C4 C8 C7 -179.2(6) . . . . ?
C6 C7 C8 C4 -0.9(9) . . . . ?
C9 C7 C8 C4 -178.7(6) . . . . ?
C6 C7 C9 C12 -179.4(6) . . . . ?
C8 C7 C9 C12 -1.5(11) . . . . ?
C6 C7 C9 C10 -0.9(7) . . . . ?
C8 C7 C9 C10 177.1(7) . . . . ?
C6 O3 C10 O4 179.5(7) . . . . ?
C6 O3 C10 C9 -0.9(8) . . . . ?
C12 C9 C10 O4 -0.9(13) . . . . ?
C7 C9 C10 O4 -179.4(8) . . . . ?
C12 C9 C10 O3 179.6(6) . . . . ?
C7 C9 C10 O3 1.1(7) . . . . ?
C7 C9 C12 C11 178.5(6) . . . . ?
C10 C9 C12 C11 0.2(12) . . . . ?
C13 C11 C12 C9 18.5(12) . . . . ?
C16 C11 C12 C9 -167.6(7) . . . . ?
Fe1 C11 C12 C9 109.9(7) . . . . ?
C12 C11 C13 C14 176.0(7) . . . . ?
C16 C11 C13 C14 1.5(8) . . . . ?
Fe1 C11 C13 C14 59.6(5) . . . . ?
C12 C11 C13 Fe1 116.3(8) . . . . ?
C16 C11 C13 Fe1 -58.2(5) . . . . ?
C11 C13 C14 C15 -0.4(9) . . . . ?
Fe1 C13 C14 C15 59.4(6) . . . . ?
C11 C13 C14 Fe1 -59.8(5) . . . . ?
C13 C14 C15 C16 -0.9(9) . . . . ?
Fe1 C14 C15 C16 58.4(5) . . . . ?
C13 C14 C15 Fe1 -59.2(5) . . . . ?
C14 C15 C16 C11 1.8(8) . . . . ?
Fe1 C15 C16 C11 60.3(5) . . . . ?
C14 C15 C16 Fe1 -58.6(6) . . . . ?
C13 C11 C16 C15 -2.0(8) . . . . ?
C12 C11 C16 C15 -177.3(6) . . . . ?
Fe1 C11 C16 C15 -60.7(5) . . . . ?
C13 C11 C16 Fe1 58.7(5) . . . . ?
C12 C11 C16 Fe1 -116.6(6) . . . . ?
C21 C17 C18 C19 -2.2(11) . . . . ?
Fe1 C17 C18 C19 -63.2(7) . . . . ?
C21 C17 C18 Fe1 61.0(7) . . . . ?
C17 C18 C19 C20 2.8(12) . . . . ?
Fe1 C18 C19 C20 -59.2(8) . . . . ?
C17 C18 C19 Fe1 62.0(6) . . . . ?
C18 C19 C20 C21 -2.4(12) . . . . ?
Fe1 C19 C20 C21 -59.7(6) . . . . ?
C18 C19 C20 Fe1 57.3(8) . . . . ?
C18 C17 C21 C20 0.9(10) . . . . ?
Fe1 C17 C21 C20 59.8(6) . . . . ?
C18 C17 C21 Fe1 -58.8(6) . . . . ?
C19 C20 C21 C17 0.8(10) . . . . ?
Fe1 C20 C21 C17 -58.8(7) . . . . ?
C19 C20 C21 Fe1 59.6(6) . . . . ?

_refine_diff_density_max         1.093
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.369



####################################################################### 
# 
# 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_GNDU009
_database_code_depnum_ccdc_archive 'CCDC 1499221'
_audit_update_record             
;
2016-08-15 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 Fe2 O4'
_chemical_formula_weight         582.19

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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.7110(9)
_cell_length_b                   11.4560(11)
_cell_length_c                   12.5503(14)
_cell_angle_alpha                64.979(10)
_cell_angle_beta                 78.462(8)
_cell_angle_gamma                70.710(8)
_cell_volume                     1313.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3356
_cell_measurement_theta_min      3.5060
_cell_measurement_theta_max      29.6100

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.140
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_T_min  0.68495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            9575
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.198
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4618
_reflns_number_gt                3551
_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0725P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0022(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4618
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 1.27379(5) 0.52747(5) 0.89296(4) 0.0440(2) Uani 1 1 d . . . . .
Fe2 Fe 0.54825(5) 0.06893(5) 0.68496(4) 0.0425(2) Uani 1 1 d . . . . .
O1 O 0.8027(2) 0.6030(2) 0.6030(2) 0.0490(6) Uani 1 1 d . . . . .
O2 O 0.8454(3) 0.7856(3) 0.5967(3) 0.0604(8) Uani 1 1 d . . . . .
O3 O 1.1172(2) 0.0931(2) 0.6925(2) 0.0466(6) Uani 1 1 d . . . . .
O4 O 1.0936(3) -0.0768(3) 0.6607(2) 0.0546(7) Uani 1 1 d . . . . .
C1 C 0.8832(4) 0.6672(4) 0.6204(3) 0.0449(8) Uani 1 1 d . . . . .
C2 C 1.0076(3) 0.5647(3) 0.6701(3) 0.0400(8) Uani 1 1 d . . . . .
C3 C 0.9972(3) 0.4394(3) 0.6729(3) 0.0389(8) Uani 1 1 d . . . . .
C4 C 1.0837(3) 0.3119(4) 0.6966(3) 0.0413(8) Uani 1 1 d . . . . .
H4 H 1.1669 0.2880 0.7236 0.050 Uiso 1 1 calc R U . . .
C5 C 1.0388(3) 0.2226(4) 0.6778(3) 0.0414(8) Uani 1 1 d . . . . .
C6 C 1.0447(4) 0.0349(4) 0.6580(3) 0.0422(8) Uani 1 1 d . . . . .
C7 C 0.9141(3) 0.1296(3) 0.6263(3) 0.0367(7) Uani 1 1 d . . . . .
C8 C 0.9151(3) 0.2501(3) 0.6385(3) 0.0385(8) Uani 1 1 d . . . . .
C9 C 0.8306(3) 0.3803(3) 0.6116(3) 0.0408(8) Uani 1 1 d . . . . .
H9 H 0.7484 0.4053 0.5823 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8747(3) 0.4690(3) 0.6304(3) 0.0410(8) Uani 1 1 d . . . . .
C11 C 1.1033(4) 0.6034(4) 0.6917(3) 0.0456(9) Uani 1 1 d . . . . .
H11 H 1.0884 0.6952 0.6682 0.055 Uiso 1 1 calc R U . . .
C12 C 1.2246(4) 0.5202(4) 0.7462(3) 0.0458(9) Uani 1 1 d . . . . .
C13 C 1.3454(4) 0.5603(4) 0.7242(3) 0.0541(10) Uani 1 1 d . . . . .
H13 H 1.3573 0.6417 0.6687 0.065 Uiso 1 1 calc R U . . .
C14 C 1.4405(4) 0.4594(5) 0.7981(4) 0.0615(11) Uani 1 1 d . . . . .
H14 H 1.5263 0.4613 0.7993 0.074 Uiso 1 1 calc R U . . .
C15 C 1.3850(4) 0.3539(5) 0.8705(4) 0.0600(11) Uani 1 1 d . . . . .
H15 H 1.4278 0.2743 0.9282 0.072 Uiso 1 1 calc R U . . .
C16 C 1.2531(4) 0.3888(4) 0.8415(3) 0.0522(10) Uani 1 1 d . . . . .
H16 H 1.1945 0.3364 0.8773 0.063 Uiso 1 1 calc R U . . .
C17 C 1.1143(5) 0.6512(6) 0.9466(5) 0.0752(14) Uani 1 1 d . . . . .
H17 H 1.0328 0.6899 0.9135 0.090 Uiso 1 1 calc R U . . .
C18 C 1.2206(5) 0.7056(4) 0.9119(4) 0.0668(12) Uani 1 1 d . . . . .
H18 H 1.2223 0.7877 0.8513 0.080 Uiso 1 1 calc R U . . .
C19 C 1.3265(5) 0.6159(5) 0.9835(4) 0.0619(11) Uani 1 1 d . . . . .
H19 H 1.4092 0.6287 0.9786 0.074 Uiso 1 1 calc R U . . .
C20 C 1.2839(6) 0.5047(5) 1.0629(4) 0.0704(13) Uani 1 1 d . . . . .
H20 H 1.3340 0.4298 1.1198 0.085 Uiso 1 1 calc R U . . .
C21 C 1.1523(6) 0.5251(6) 1.0422(4) 0.0818(16) Uani 1 1 d . . . . .
H21 H 1.0999 0.4671 1.0834 0.098 Uiso 1 1 calc R U . . .
C22 C 0.8255(3) 0.0903(4) 0.5943(3) 0.0402(8) Uani 1 1 d . . . . .
H22 H 0.8596 0.0083 0.5861 0.048 Uiso 1 1 calc R U . . .
C23 C 0.6878(3) 0.1543(3) 0.5710(3) 0.0389(8) Uani 1 1 d . . . . .
C24 C 0.5914(4) 0.2486(4) 0.6155(3) 0.0507(9) Uani 1 1 d . . . . .
H24 H 0.6091 0.2899 0.6583 0.061 Uiso 1 1 calc R U . . .
C25 C 0.4655(4) 0.2669(4) 0.5824(3) 0.0532(10) Uani 1 1 d . . . . .
H25 H 0.3863 0.3237 0.5989 0.064 Uiso 1 1 calc R U . . .
C26 C 0.4802(4) 0.1850(4) 0.5204(3) 0.0562(11) Uani 1 1 d . . . . .
H26 H 0.4122 0.1787 0.4889 0.067 Uiso 1 1 calc R U . . .
C27 C 0.6154(4) 0.1140(4) 0.5141(3) 0.0436(9) Uani 1 1 d . . . . .
H27 H 0.6514 0.0519 0.4790 0.052 Uiso 1 1 calc R U . . .
C28 C 0.6458(4) -0.1025(5) 0.8128(3) 0.0643(13) Uani 1 1 d . . . . .
H28 H 0.7372 -0.1383 0.8160 0.077 Uiso 1 1 calc R U . . .
C29 C 0.5644(6) -0.0099(5) 0.8608(4) 0.0730(14) Uani 1 1 d . . . . .
H29 H 0.5940 0.0266 0.9013 0.088 Uiso 1 1 calc R U . . .
C30 C 0.4350(5) 0.0186(5) 0.8395(4) 0.0766(15) Uani 1 1 d . . . . .
H30 H 0.3624 0.0772 0.8623 0.092 Uiso 1 1 calc R U . . .
C31 C 0.4327(5) -0.0575(5) 0.7765(5) 0.0782(16) Uani 1 1 d . . . . .
H31 H 0.3578 -0.0591 0.7510 0.094 Uiso 1 1 calc R U . . .
C32 C 0.5632(5) -0.1303(5) 0.7593(4) 0.0699(13) Uani 1 1 d . . . . .
H32 H 0.5902 -0.1875 0.7190 0.084 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 C13 2.020(4) . ?
Fe1 C17 2.032(5) . ?
Fe1 C18 2.033(5) . ?
Fe1 C16 2.037(4) . ?
Fe1 C21 2.052(5) . ?
Fe1 C12 2.055(4) . ?
Fe1 C15 2.055(4) . ?
Fe1 C20 2.057(4) . ?
Fe1 C14 2.057(4) . ?
Fe1 C19 2.060(4) . ?
Fe2 C27 2.019(3) . ?
Fe2 C29 2.020(4) . ?
Fe2 C32 2.030(5) . ?
Fe2 C30 2.035(4) . ?
Fe2 C24 2.039(4) . ?
Fe2 C31 2.039(4) . ?
Fe2 C23 2.040(3) . ?
Fe2 C28 2.043(4) . ?
Fe2 C26 2.051(3) . ?
Fe2 C25 2.061(4) . ?
O1 C10 1.395(4) . ?
O1 C1 1.400(4) . ?
O2 C1 1.199(5) . ?
O3 C5 1.395(4) . ?
O3 C6 1.399(4) . ?
O4 C6 1.200(4) . ?
C1 C2 1.491(5) . ?
C2 C11 1.354(5) . ?
C2 C3 1.461(5) . ?
C3 C4 1.389(5) . ?
C3 C10 1.398(5) . ?
C4 C5 1.381(5) . ?
C4 H4 0.9300 . ?
C5 C8 1.397(5) . ?
C6 C7 1.465(5) . ?
C7 C22 1.360(5) . ?
C7 C8 1.455(5) . ?
C8 C9 1.401(5) . ?
C9 C10 1.371(5) . ?
C9 H9 0.9300 . ?
C11 C12 1.433(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.449(5) . ?
C12 C16 1.452(5) . ?
C13 C14 1.388(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.403(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.414(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.384(7) . ?
C17 C21 1.426(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.416(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.398(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.409(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.441(5) . ?
C22 H22 0.9300 . ?
C23 C27 1.435(5) . ?
C23 C24 1.445(5) . ?
C24 C25 1.413(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.408(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.414(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C32 1.392(7) . ?
C28 C29 1.403(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.369(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.412(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.399(7) . ?
C31 H31 0.9300 . ?
C32 H32 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
C13 Fe1 C17 125.6(2) . . ?
C13 Fe1 C18 107.56(19) . . ?
C17 Fe1 C18 39.8(2) . . ?
C13 Fe1 C16 68.82(17) . . ?
C17 Fe1 C16 121.54(19) . . ?
C18 Fe1 C16 155.70(18) . . ?
C13 Fe1 C21 164.0(2) . . ?
C17 Fe1 C21 40.9(2) . . ?
C18 Fe1 C21 67.5(2) . . ?
C16 Fe1 C21 109.02(19) . . ?
C13 Fe1 C12 41.65(15) . . ?
C17 Fe1 C12 107.10(18) . . ?
C18 Fe1 C12 119.54(17) . . ?
C16 Fe1 C12 41.58(14) . . ?
C21 Fe1 C12 126.1(2) . . ?
C13 Fe1 C15 67.42(18) . . ?
C17 Fe1 C15 156.9(2) . . ?
C18 Fe1 C15 162.2(2) . . ?
C16 Fe1 C15 40.41(16) . . ?
C21 Fe1 C15 122.0(2) . . ?
C12 Fe1 C15 68.93(15) . . ?
C13 Fe1 C20 153.8(2) . . ?
C17 Fe1 C20 68.0(2) . . ?
C18 Fe1 C20 67.34(19) . . ?
C16 Fe1 C20 126.56(17) . . ?
C21 Fe1 C20 40.1(2) . . ?
C12 Fe1 C20 163.71(19) . . ?
C15 Fe1 C20 109.14(18) . . ?
C13 Fe1 C14 39.80(17) . . ?
C17 Fe1 C14 161.8(2) . . ?
C18 Fe1 C14 125.5(2) . . ?
C16 Fe1 C14 68.01(18) . . ?
C21 Fe1 C14 155.5(2) . . ?
C12 Fe1 C14 68.89(16) . . ?
C15 Fe1 C14 39.90(18) . . ?
C20 Fe1 C14 120.7(2) . . ?
C13 Fe1 C19 119.62(18) . . ?
C17 Fe1 C19 67.73(19) . . ?
C18 Fe1 C19 40.49(17) . . ?
C16 Fe1 C19 162.54(16) . . ?
C21 Fe1 C19 67.3(2) . . ?
C12 Fe1 C19 154.54(17) . . ?
C15 Fe1 C19 125.69(17) . . ?
C20 Fe1 C19 39.68(18) . . ?
C14 Fe1 C19 107.82(18) . . ?
C27 Fe2 C29 155.7(2) . . ?
C27 Fe2 C32 107.61(18) . . ?
C29 Fe2 C32 67.2(2) . . ?
C27 Fe2 C30 163.0(2) . . ?
C29 Fe2 C30 39.4(2) . . ?
C32 Fe2 C30 68.0(2) . . ?
C27 Fe2 C24 69.33(16) . . ?
C29 Fe2 C24 108.35(19) . . ?
C32 Fe2 C24 163.21(19) . . ?
C30 Fe2 C24 119.7(2) . . ?
C27 Fe2 C31 125.6(2) . . ?
C29 Fe2 C31 66.8(2) . . ?
C32 Fe2 C31 40.2(2) . . ?
C30 Fe2 C31 40.5(2) . . ?
C24 Fe2 C31 154.8(2) . . ?
C27 Fe2 C23 41.41(13) . . ?
C29 Fe2 C23 120.67(18) . . ?
C32 Fe2 C23 125.44(18) . . ?
C30 Fe2 C23 154.5(2) . . ?
C24 Fe2 C23 41.48(14) . . ?
C31 Fe2 C23 162.9(2) . . ?
C27 Fe2 C28 120.24(17) . . ?
C29 Fe2 C28 40.40(19) . . ?
C32 Fe2 C28 39.97(19) . . ?
C30 Fe2 C28 67.68(19) . . ?
C24 Fe2 C28 126.22(19) . . ?
C31 Fe2 C28 67.34(19) . . ?
C23 Fe2 C28 107.50(16) . . ?
C27 Fe2 C26 40.64(15) . . ?
C29 Fe2 C26 162.7(2) . . ?
C32 Fe2 C26 120.99(19) . . ?
C30 Fe2 C26 126.29(19) . . ?
C24 Fe2 C26 68.14(16) . . ?
C31 Fe2 C26 108.65(18) . . ?
C23 Fe2 C26 68.73(14) . . ?
C28 Fe2 C26 155.2(2) . . ?
C27 Fe2 C25 68.30(16) . . ?
C29 Fe2 C25 126.5(2) . . ?
C32 Fe2 C25 155.32(19) . . ?
C30 Fe2 C25 108.44(19) . . ?
C24 Fe2 C25 40.31(15) . . ?
C31 Fe2 C25 121.04(17) . . ?
C23 Fe2 C25 68.62(14) . . ?
C28 Fe2 C25 163.4(2) . . ?
C26 Fe2 C25 40.06(17) . . ?
C10 O1 C1 107.3(3) . . ?
C5 O3 C6 107.0(3) . . ?
O2 C1 O1 119.9(3) . . ?
O2 C1 C2 131.6(4) . . ?
O1 C1 C2 108.5(3) . . ?
C11 C2 C3 135.0(3) . . ?
C11 C2 C1 119.5(3) . . ?
C3 C2 C1 105.2(3) . . ?
C4 C3 C10 118.8(3) . . ?
C4 C3 C2 134.3(3) . . ?
C10 C3 C2 106.6(3) . . ?
C5 C4 C3 116.0(3) . . ?
C5 C4 H4 122.0 . . ?
C3 C4 H4 122.0 . . ?
C4 C5 O3 122.4(3) . . ?
C4 C5 C8 125.5(3) . . ?
O3 C5 C8 112.0(3) . . ?
O4 C6 O3 119.2(3) . . ?
O4 C6 C7 132.0(3) . . ?
O3 C6 C7 108.9(3) . . ?
C22 C7 C8 135.9(3) . . ?
C22 C7 C6 118.3(3) . . ?
C8 C7 C6 105.8(3) . . ?
C5 C8 C9 117.8(3) . . ?
C5 C8 C7 106.2(3) . . ?
C9 C8 C7 135.7(3) . . ?
C10 C9 C8 116.8(3) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C9 C10 O1 122.6(3) . . ?
C9 C10 C3 125.0(3) . . ?
O1 C10 C3 112.3(3) . . ?
C2 C11 C12 128.0(4) . . ?
C2 C11 H11 116.0 . . ?
C12 C11 H11 116.0 . . ?
C11 C12 C13 125.1(3) . . ?
C11 C12 C16 130.1(3) . . ?
C13 C12 C16 104.4(3) . . ?
C11 C12 Fe1 122.2(3) . . ?
C13 C12 Fe1 67.9(2) . . ?
C16 C12 Fe1 68.6(2) . . ?
C14 C13 C12 110.1(4) . . ?
C14 C13 Fe1 71.5(2) . . ?
C12 C13 Fe1 70.4(2) . . ?
C14 C13 H13 125.0 . . ?
C12 C13 H13 125.0 . . ?
Fe1 C13 H13 124.7 . . ?
C13 C14 C15 108.3(4) . . ?
C13 C14 Fe1 68.7(2) . . ?
C15 C14 Fe1 70.0(3) . . ?
C13 C14 H14 125.9 . . ?
C15 C14 H14 125.9 . . ?
Fe1 C14 H14 127.0 . . ?
C14 C15 C16 108.8(4) . . ?
C14 C15 Fe1 70.1(3) . . ?
C16 C15 Fe1 69.1(2) . . ?
C14 C15 H15 125.6 . . ?
C16 C15 H15 125.6 . . ?
Fe1 C15 H15 126.7 . . ?
C15 C16 C12 108.5(4) . . ?
C15 C16 Fe1 70.5(2) . . ?
C12 C16 Fe1 69.9(2) . . ?
C15 C16 H16 125.8 . . ?
C12 C16 H16 125.8 . . ?
Fe1 C16 H16 125.5 . . ?
C18 C17 C21 107.6(5) . . ?
C18 C17 Fe1 70.1(3) . . ?
C21 C17 Fe1 70.3(3) . . ?
C18 C17 H17 126.2 . . ?
C21 C17 H17 126.2 . . ?
Fe1 C17 H17 125.0 . . ?
C17 C18 C19 109.0(4) . . ?
C17 C18 Fe1 70.1(3) . . ?
C19 C18 Fe1 70.8(3) . . ?
C17 C18 H18 125.5 . . ?
C19 C18 H18 125.5 . . ?
Fe1 C18 H18 125.2 . . ?
C20 C19 C18 107.4(4) . . ?
C20 C19 Fe1 70.0(3) . . ?
C18 C19 Fe1 68.7(2) . . ?
C20 C19 H19 126.3 . . ?
C18 C19 H19 126.3 . . ?
Fe1 C19 H19 126.5 . . ?
C19 C20 C21 108.5(4) . . ?
C19 C20 Fe1 70.3(2) . . ?
C21 C20 Fe1 69.7(3) . . ?
C19 C20 H20 125.7 . . ?
C21 C20 H20 125.7 . . ?
Fe1 C20 H20 125.8 . . ?
C20 C21 C17 107.4(4) . . ?
C20 C21 Fe1 70.2(3) . . ?
C17 C21 Fe1 68.8(3) . . ?
C20 C21 H21 126.3 . . ?
C17 C21 H21 126.3 . . ?
Fe1 C21 H21 126.3 . . ?
C7 C22 C23 130.8(3) . . ?
C7 C22 H22 114.6 . . ?
C23 C22 H22 114.6 . . ?
C27 C23 C22 123.6(3) . . ?
C27 C23 C24 106.5(3) . . ?
C22 C23 C24 129.0(3) . . ?
C27 C23 Fe2 68.5(2) . . ?
C22 C23 Fe2 118.8(2) . . ?
C24 C23 Fe2 69.2(2) . . ?
C25 C24 C23 108.0(4) . . ?
C25 C24 Fe2 70.7(2) . . ?
C23 C24 Fe2 69.3(2) . . ?
C25 C24 H24 126.0 . . ?
C23 C24 H24 126.0 . . ?
Fe2 C24 H24 125.6 . . ?
C26 C25 C24 108.6(4) . . ?
C26 C25 Fe2 69.6(2) . . ?
C24 C25 Fe2 69.0(2) . . ?
C26 C25 H25 125.7 . . ?
C24 C25 H25 125.7 . . ?
Fe2 C25 H25 127.3 . . ?
C25 C26 C27 108.5(3) . . ?
C25 C26 Fe2 70.4(2) . . ?
C27 C26 Fe2 68.48(19) . . ?
C25 C26 H26 125.7 . . ?
C27 C26 H26 125.7 . . ?
Fe2 C26 H26 127.0 . . ?
C26 C27 C23 108.3(3) . . ?
C26 C27 Fe2 70.9(2) . . ?
C23 C27 Fe2 70.09(19) . . ?
C26 C27 H27 125.9 . . ?
C23 C27 H27 125.9 . . ?
Fe2 C27 H27 124.8 . . ?
C32 C28 C29 106.7(4) . . ?
C32 C28 Fe2 69.5(2) . . ?
C29 C28 Fe2 68.9(2) . . ?
C32 C28 H28 126.6 . . ?
C29 C28 H28 126.6 . . ?
Fe2 C28 H28 126.4 . . ?
C30 C29 C28 110.0(5) . . ?
C30 C29 Fe2 70.9(3) . . ?
C28 C29 Fe2 70.7(2) . . ?
C30 C29 H29 125.0 . . ?
C28 C29 H29 125.0 . . ?
Fe2 C29 H29 125.1 . . ?
C29 C30 C31 107.1(5) . . ?
C29 C30 Fe2 69.7(3) . . ?
C31 C30 Fe2 69.9(3) . . ?
C29 C30 H30 126.5 . . ?
C31 C30 H30 126.5 . . ?
Fe2 C30 H30 125.5 . . ?
C32 C31 C30 107.9(5) . . ?
C32 C31 Fe2 69.6(3) . . ?
C30 C31 Fe2 69.6(3) . . ?
C32 C31 H31 126.1 . . ?
C30 C31 H31 126.1 . . ?
Fe2 C31 H31 126.4 . . ?
C28 C32 C31 108.3(5) . . ?
C28 C32 Fe2 70.5(3) . . ?
C31 C32 Fe2 70.2(3) . . ?
C28 C32 H32 125.8 . . ?
C31 C32 H32 125.8 . . ?
Fe2 C32 H32 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
C10 O1 C1 O2 176.2(4) . . . . ?
C10 O1 C1 C2 -4.6(4) . . . . ?
O2 C1 C2 C11 -2.6(6) . . . . ?
O1 C1 C2 C11 178.2(3) . . . . ?
O2 C1 C2 C3 -177.2(4) . . . . ?
O1 C1 C2 C3 3.6(4) . . . . ?
C11 C2 C3 C4 -1.7(7) . . . . ?
C1 C2 C3 C4 171.7(4) . . . . ?
C11 C2 C3 C10 -174.6(4) . . . . ?
C1 C2 C3 C10 -1.2(4) . . . . ?
C10 C3 C4 C5 -1.3(5) . . . . ?
C2 C3 C4 C5 -173.5(4) . . . . ?
C3 C4 C5 O3 176.9(3) . . . . ?
C3 C4 C5 C8 -0.6(5) . . . . ?
C6 O3 C5 C4 -175.7(3) . . . . ?
C6 O3 C5 C8 2.1(4) . . . . ?
C5 O3 C6 O4 178.5(3) . . . . ?
C5 O3 C6 C7 -2.9(4) . . . . ?
O4 C6 C7 C22 0.9(6) . . . . ?
O3 C6 C7 C22 -177.5(3) . . . . ?
O4 C6 C7 C8 -179.0(4) . . . . ?
O3 C6 C7 C8 2.6(4) . . . . ?
C4 C5 C8 C9 2.5(5) . . . . ?
O3 C5 C8 C9 -175.2(3) . . . . ?
C4 C5 C8 C7 177.3(3) . . . . ?
O3 C5 C8 C7 -0.4(4) . . . . ?
C22 C7 C8 C5 178.8(4) . . . . ?
C6 C7 C8 C5 -1.4(3) . . . . ?
C22 C7 C8 C9 -7.8(7) . . . . ?
C6 C7 C8 C9 172.1(4) . . . . ?
C5 C8 C9 C10 -2.4(5) . . . . ?
C7 C8 C9 C10 -175.3(4) . . . . ?
C8 C9 C10 O1 177.5(3) . . . . ?
C8 C9 C10 C3 0.7(5) . . . . ?
C1 O1 C10 C9 -173.2(3) . . . . ?
C1 O1 C10 C3 3.9(4) . . . . ?
C4 C3 C10 C9 1.2(5) . . . . ?
C2 C3 C10 C9 175.4(3) . . . . ?
C4 C3 C10 O1 -175.8(3) . . . . ?
C2 C3 C10 O1 -1.6(4) . . . . ?
C3 C2 C11 C12 -12.0(7) . . . . ?
C1 C2 C11 C12 175.3(3) . . . . ?
C2 C11 C12 C13 152.1(4) . . . . ?
C2 C11 C12 C16 -35.6(6) . . . . ?
C2 C11 C12 Fe1 -123.6(4) . . . . ?
C11 C12 C13 C14 175.5(4) . . . . ?
C16 C12 C13 C14 1.6(5) . . . . ?
Fe1 C12 C13 C14 60.8(3) . . . . ?
C11 C12 C13 Fe1 114.7(4) . . . . ?
C16 C12 C13 Fe1 -59.2(3) . . . . ?
C12 C13 C14 C15 -1.2(5) . . . . ?
Fe1 C13 C14 C15 58.9(3) . . . . ?
C12 C13 C14 Fe1 -60.1(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
Fe1 C14 C15 C16 58.4(3) . . . . ?
C13 C14 C15 Fe1 -58.1(3) . . . . ?
C14 C15 C16 C12 0.7(5) . . . . ?
Fe1 C15 C16 C12 59.8(3) . . . . ?
C14 C15 C16 Fe1 -59.1(3) . . . . ?
C11 C12 C16 C15 -174.8(4) . . . . ?
C13 C12 C16 C15 -1.4(4) . . . . ?
Fe1 C12 C16 C15 -60.2(3) . . . . ?
C11 C12 C16 Fe1 -114.7(4) . . . . ?
C13 C12 C16 Fe1 58.8(3) . . . . ?
C21 C17 C18 C19 0.3(6) . . . . ?
Fe1 C17 C18 C19 -60.3(3) . . . . ?
C21 C17 C18 Fe1 60.6(3) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
Fe1 C18 C19 C20 -59.6(3) . . . . ?
C17 C18 C19 Fe1 59.9(3) . . . . ?
C18 C19 C20 C21 -0.7(5) . . . . ?
Fe1 C19 C20 C21 -59.5(3) . . . . ?
C18 C19 C20 Fe1 58.8(3) . . . . ?
C19 C20 C21 C17 0.9(5) . . . . ?
Fe1 C20 C21 C17 -58.9(3) . . . . ?
C19 C20 C21 Fe1 59.8(3) . . . . ?
C18 C17 C21 C20 -0.7(6) . . . . ?
Fe1 C17 C21 C20 59.8(3) . . . . ?
C18 C17 C21 Fe1 -60.5(3) . . . . ?
C8 C7 C22 C23 -7.5(6) . . . . ?
C6 C7 C22 C23 172.7(3) . . . . ?
C7 C22 C23 C27 166.2(3) . . . . ?
C7 C22 C23 C24 -26.1(6) . . . . ?
C7 C22 C23 Fe2 -111.7(4) . . . . ?
C27 C23 C24 C25 -1.8(4) . . . . ?
C22 C23 C24 C25 -171.1(3) . . . . ?
Fe2 C23 C24 C25 -60.3(3) . . . . ?
C27 C23 C24 Fe2 58.6(2) . . . . ?
C22 C23 C24 Fe2 -110.8(4) . . . . ?
C23 C24 C25 C26 1.0(4) . . . . ?
Fe2 C24 C25 C26 -58.5(3) . . . . ?
C23 C24 C25 Fe2 59.5(2) . . . . ?
C24 C25 C26 C27 0.1(4) . . . . ?
Fe2 C25 C26 C27 -58.0(2) . . . . ?
C24 C25 C26 Fe2 58.1(3) . . . . ?
C25 C26 C27 C23 -1.3(4) . . . . ?
Fe2 C26 C27 C23 -60.4(2) . . . . ?
C25 C26 C27 Fe2 59.1(3) . . . . ?
C22 C23 C27 C26 171.9(3) . . . . ?
C24 C23 C27 C26 1.9(4) . . . . ?
Fe2 C23 C27 C26 60.9(2) . . . . ?
C22 C23 C27 Fe2 111.0(3) . . . . ?
C24 C23 C27 Fe2 -59.0(2) . . . . ?
C32 C28 C29 C30 0.6(5) . . . . ?
Fe2 C28 C29 C30 60.1(3) . . . . ?
C32 C28 C29 Fe2 -59.6(3) . . . . ?
C28 C29 C30 C31 0.2(5) . . . . ?
Fe2 C29 C30 C31 60.2(3) . . . . ?
C28 C29 C30 Fe2 -60.0(3) . . . . ?
C29 C30 C31 C32 -0.9(5) . . . . ?
Fe2 C30 C31 C32 59.2(3) . . . . ?
C29 C30 C31 Fe2 -60.1(3) . . . . ?
C29 C28 C32 C31 -1.1(5) . . . . ?
Fe2 C28 C32 C31 -60.3(3) . . . . ?
C29 C28 C32 Fe2 59.2(3) . . . . ?
C30 C31 C32 C28 1.2(5) . . . . ?
Fe2 C31 C32 C28 60.5(3) . . . . ?
C30 C31 C32 Fe2 -59.2(3) . . . . ?

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.078



