# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_cl023
_database_code_depnum_ccdc_archive 'CCDC 1053319'
_audit_update_record             
;
2015-03-11 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT019_cl023               
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.931 Why ? 
RESPONSE: poorly diffracting crystal
;
_audit_creation_date             2014-05-16
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '[FeL5i(azpy)]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 Fe N6 O6'
_chemical_formula_sum            'C28 H26 Fe N6 O6'
_chemical_formula_weight         598.40

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      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                   10.651(1)
_cell_length_b                   10.802(1)
_cell_length_c                   12.528(1)
_cell_angle_alpha                97.671(4)
_cell_angle_beta                 92.238(4)
_cell_angle_gamma                110.803(3)
_cell_volume                     1329.5(1)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    10415
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'image-plate area detector'
_diffrn_measurement_device_type  STOE-IPDSII
_diffrn_measurement_method       Omega-Scan
_diffrn_reflns_number            15884
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.647
_diffrn_reflns_theta_max         24.569
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.928
_reflns_number_total             4464
_reflns_number_gt                3376
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²] 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         4464
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_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
C1 C 0.4493(2) 0.0509(3) 0.8419(2) 0.0279(6) Uani 1 1 d . . . . .
C2 C 0.4871(2) -0.0309(2) 0.76010(19) 0.0270(5) Uani 1 1 d . . . . .
C3 C 0.5711(2) 0.0206(2) 0.6792(2) 0.0273(5) Uani 1 1 d . . . . .
H3 H 0.5902 -0.0421 0.6281 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7052(2) 0.1883(2) 0.58205(19) 0.0256(5) Uani 1 1 d . . . . .
C5 C 0.7367(3) 0.1045(3) 0.5015(2) 0.0325(6) Uani 1 1 d . . . . .
H5 H 0.7033 0.0104 0.5012 0.039 Uiso 1 1 calc R U . . .
C6 C 0.8160(3) 0.1575(3) 0.4223(2) 0.0345(6) Uani 1 1 d . . . . .
H6 H 0.8375 0.0998 0.3681 0.041 Uiso 1 1 calc R U . . .
C7 C 0.8645(2) 0.2946(3) 0.4213(2) 0.0319(6) Uani 1 1 d . . . . .
H7 H 0.9181 0.3304 0.3659 0.038 Uiso 1 1 calc R U . . .
C8 C 0.8353(2) 0.3794(3) 0.50066(19) 0.0288(6) Uani 1 1 d . . . . .
H8 H 0.8690 0.4732 0.4997 0.035 Uiso 1 1 calc R U . . .
C9 C 0.7564(2) 0.3278(2) 0.58223(19) 0.0256(5) Uani 1 1 d . . . . .
C10 C 0.7742(2) 0.5335(2) 0.68884(19) 0.0272(6) Uani 1 1 d . . . . .
H10 H 0.8334 0.5754 0.6386 0.033 Uiso 1 1 calc R U . . .
C11 C 0.7510(2) 0.6194(2) 0.77600(19) 0.0260(5) Uani 1 1 d . . . . .
C12 C 0.6597(2) 0.5713(2) 0.85481(19) 0.0262(5) Uani 1 1 d . . . . .
C13 C 0.3477(3) -0.0066(3) 0.9194(2) 0.0419(7) Uani 1 1 d . . . . .
H13A H 0.3370 0.0666 0.9689 0.063 Uiso 1 1 calc R U . . .
H13B H 0.3791 -0.0623 0.9611 0.063 Uiso 1 1 calc R U . . .
H13C H 0.2608 -0.0615 0.8788 0.063 Uiso 1 1 calc R U . . .
C14 C 0.4329(2) -0.1773(3) 0.7560(2) 0.0297(6) Uani 1 1 d . . . . .
C15 C 0.4286(3) -0.3866(2) 0.6700(2) 0.0372(6) Uani 1 1 d . . . . .
H15A H 0.4466 -0.4112 0.7399 0.056 Uiso 1 1 calc R U . . .
H15B H 0.4717 -0.4260 0.6145 0.056 Uiso 1 1 calc R U . . .
H15C H 0.3310 -0.4204 0.6503 0.056 Uiso 1 1 calc R U . . .
C16 C 0.6239(3) 0.6616(3) 0.9406(2) 0.0318(6) Uani 1 1 d . . . . .
H16A H 0.5529 0.6071 0.9806 0.048 Uiso 1 1 calc R U . . .
H16B H 0.5914 0.7226 0.9065 0.048 Uiso 1 1 calc R U . . .
H16C H 0.7039 0.7140 0.9906 0.048 Uiso 1 1 calc R U . . .
C17 C 0.8293(3) 0.7618(3) 0.7738(2) 0.0305(6) Uani 1 1 d . . . . .
C18 C 0.8929(5) 0.9867(3) 0.8547(3) 0.0859(15) Uani 1 1 d . . . . .
H18A H 0.9899 1.0052 0.8555 0.129 Uiso 1 1 calc R U . . .
H18B H 0.8756 1.0408 0.9176 0.129 Uiso 1 1 calc R U . . .
H18C H 0.8610 1.0094 0.7883 0.129 Uiso 1 1 calc R U . . .
C19 C 0.7710(2) 0.3235(2) 0.96704(19) 0.0276(6) Uani 1 1 d . . . . .
H19 H 0.6918 0.3259 0.9981 0.033 Uiso 1 1 calc R U . . .
C20 C 0.8810(2) 0.3338(2) 1.0349(2) 0.0298(6) Uani 1 1 d . . . . .
H20 H 0.8763 0.3430 1.1109 0.036 Uiso 1 1 calc R U . . .
C21 C 0.9978(2) 0.3309(2) 0.9921(2) 0.0304(6) Uani 1 1 d . . . . .
H21 H 1.0747 0.3387 1.0374 0.036 Uiso 1 1 calc R U . . .
C22 C 0.9982(2) 0.3160(2) 0.8802(2) 0.0274(6) Uani 1 1 d . . . . .
C23 C 0.8849(2) 0.3069(2) 0.8173(2) 0.0275(5) Uani 1 1 d . . . . .
H23 H 0.8873 0.2979 0.7411 0.033 Uiso 1 1 calc R U . . .
C24 C 1.3377(2) 0.2900(2) 0.7335(2) 0.0269(5) Uani 1 1 d . . . . .
H24 H 1.3467 0.3024 0.8103 0.032 Uiso 1 1 calc R U . . .
C25 C 1.2168(2) 0.2805(2) 0.6804(2) 0.0279(6) Uani 1 1 d . . . . .
C26 C 1.2007(2) 0.2610(3) 0.5681(2) 0.0316(6) Uani 1 1 d . . . . .
H26 H 1.1180 0.2522 0.5305 0.038 Uiso 1 1 calc R U . . .
C27 C 1.3084(2) 0.2549(3) 0.5130(2) 0.0304(6) Uani 1 1 d . . . . .
H27 H 1.3018 0.2434 0.4362 0.036 Uiso 1 1 calc R U . . .
C28 C 1.4257(2) 0.2656(2) 0.57065(19) 0.0275(5) Uani 1 1 d . . . . .
H28 H 1.4990 0.2613 0.5316 0.033 Uiso 1 1 calc R U . . .
N1 N 0.62495(18) 0.1478(2) 0.66882(16) 0.0254(5) Uani 1 1 d . . . . .
N2 N 0.72175(19) 0.40228(19) 0.67139(15) 0.0250(4) Uani 1 1 d . . . . .
N3 N 0.77155(19) 0.31008(19) 0.85866(16) 0.0264(5) Uani 1 1 d . . . . .
N4 N 1.1174(2) 0.3093(2) 0.83363(16) 0.0308(5) Uani 1 1 d . . . . .
N5 N 1.1030(2) 0.2889(2) 0.73306(17) 0.0347(5) Uani 1 1 d . . . . .
N6 N 1.44177(19) 0.28215(19) 0.68016(16) 0.0261(5) Uani 1 1 d . . . . .
O1 O 0.49548(15) 0.17842(16) 0.85375(13) 0.0264(4) Uani 1 1 d . . . . .
O2 O 0.59891(16) 0.44666(16) 0.85693(13) 0.0265(4) Uani 1 1 d . . . . .
O3 O 0.3550(2) -0.24029(18) 0.81379(15) 0.0425(5) Uani 1 1 d . . . . .
O4 O 0.48210(19) -0.24253(17) 0.67765(15) 0.0379(5) Uani 1 1 d . . . . .
O5 O 0.89859(19) 0.80348(18) 0.70240(15) 0.0429(5) Uani 1 1 d . . . . .
O6 O 0.8221(3) 0.84600(19) 0.85888(18) 0.0679(8) Uani 1 1 d . . . . .
Fe1 Fe 0.61011(3) 0.29428(4) 0.76335(3) 0.02374(11) 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
C1 O1 1.273(3) . ?
C1 C2 1.427(3) . ?
C1 C13 1.505(3) . ?
C2 C3 1.416(3) . ?
C2 C14 1.470(4) . ?
C3 N1 1.314(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 C9 1.408(3) . ?
C4 N1 1.428(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(3) . ?
C8 H8 0.9500 . ?
C9 N2 1.426(3) . ?
C10 N2 1.309(3) . ?
C10 C11 1.424(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.429(3) . ?
C11 C17 1.472(4) . ?
C12 O2 1.274(3) . ?
C12 C16 1.507(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O3 1.206(3) . ?
C14 O4 1.361(3) . ?
C15 O4 1.443(3) . ?
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 O5 1.213(3) . ?
C17 O6 1.329(3) . ?
C18 O6 1.446(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N3 1.347(3) . ?
C19 C20 1.382(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(3) . ?
C22 N4 1.438(3) . ?
C23 N3 1.342(3) . ?
C23 H23 0.9500 . ?
C24 N6 1.339(3) . ?
C24 C25 1.390(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(4) . ?
C25 N5 1.428(3) . ?
C26 C27 1.378(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(4) . ?
C27 H27 0.9500 . ?
C28 N6 1.356(3) . ?
C28 H28 0.9500 . ?
N1 Fe1 1.904(2) . ?
N2 Fe1 1.893(2) . ?
N3 Fe1 1.997(2) . ?
N4 N5 1.243(3) . ?
N6 Fe1 1.992(2) 1_655 ?
O1 Fe1 1.9340(17) . ?
O2 Fe1 1.9321(18) . ?
Fe1 N6 1.992(2) 1_455 ?

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 C1 C2 123.1(2) . . ?
O1 C1 C13 114.2(2) . . ?
C2 C1 C13 122.7(2) . . ?
C3 C2 C1 123.5(2) . . ?
C3 C2 C14 117.4(2) . . ?
C1 C2 C14 119.0(2) . . ?
N1 C3 C2 125.6(2) . . ?
N1 C3 H3 117.2 . . ?
C2 C3 H3 117.2 . . ?
C5 C4 C9 119.3(2) . . ?
C5 C4 N1 126.5(2) . . ?
C9 C4 N1 114.2(2) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 119.4(2) . . ?
C8 C9 N2 126.9(2) . . ?
C4 C9 N2 113.7(2) . . ?
N2 C10 C11 126.2(2) . . ?
N2 C10 H10 116.9 . . ?
C11 C10 H10 116.9 . . ?
C10 C11 C12 123.2(2) . . ?
C10 C11 C17 112.3(2) . . ?
C12 C11 C17 124.5(2) . . ?
O2 C12 C11 122.4(2) . . ?
O2 C12 C16 113.9(2) . . ?
C11 C12 C16 123.6(2) . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 O4 119.7(2) . . ?
O3 C14 C2 127.3(2) . . ?
O4 C14 C2 112.9(2) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 O6 120.4(2) . . ?
O5 C17 C11 124.5(2) . . ?
O6 C17 C11 115.0(2) . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 122.6(2) . . ?
N3 C19 H19 118.7 . . ?
C20 C19 H19 118.7 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 117.4(2) . . ?
C20 C21 H21 121.3 . . ?
C22 C21 H21 121.3 . . ?
C23 C22 C21 119.5(2) . . ?
C23 C22 N4 122.1(2) . . ?
C21 C22 N4 118.4(2) . . ?
N3 C23 C22 123.3(2) . . ?
N3 C23 H23 118.4 . . ?
C22 C23 H23 118.4 . . ?
N6 C24 C25 122.3(2) . . ?
N6 C24 H24 118.9 . . ?
C25 C24 H24 118.9 . . ?
C26 C25 C24 119.9(2) . . ?
C26 C25 N5 115.4(2) . . ?
C24 C25 N5 124.6(2) . . ?
C27 C26 C25 117.9(2) . . ?
C27 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
C28 C27 C26 119.2(2) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
N6 C28 C27 123.4(2) . . ?
N6 C28 H28 118.3 . . ?
C27 C28 H28 118.3 . . ?
C3 N1 C4 120.9(2) . . ?
C3 N1 Fe1 125.89(17) . . ?
C4 N1 Fe1 113.22(15) . . ?
C10 N2 C9 120.5(2) . . ?
C10 N2 Fe1 125.39(17) . . ?
C9 N2 Fe1 113.87(15) . . ?
C23 N3 C19 117.2(2) . . ?
C23 N3 Fe1 121.40(17) . . ?
C19 N3 Fe1 121.43(16) . . ?
N5 N4 C22 112.4(2) . . ?
N4 N5 C25 115.9(2) . . ?
C24 N6 C28 117.2(2) . . ?
C24 N6 Fe1 119.35(17) . 1_655 ?
C28 N6 Fe1 123.42(16) . 1_655 ?
C1 O1 Fe1 128.68(15) . . ?
C12 O2 Fe1 129.06(15) . . ?
C14 O4 C15 114.3(2) . . ?
C17 O6 C18 115.4(2) . . ?
N2 Fe1 N1 85.03(9) . . ?
N2 Fe1 O2 93.25(8) . . ?
N1 Fe1 O2 178.26(8) . . ?
N2 Fe1 O1 177.99(8) . . ?
N1 Fe1 O1 92.99(8) . . ?
O2 Fe1 O1 88.74(7) . . ?
N2 Fe1 N6 92.67(9) . 1_455 ?
N1 Fe1 N6 92.41(8) . 1_455 ?
O2 Fe1 N6 87.83(8) . 1_455 ?
O1 Fe1 N6 87.11(8) . 1_455 ?
N2 Fe1 N3 90.82(9) . . ?
N1 Fe1 N3 91.57(9) . . ?
O2 Fe1 N3 88.28(8) . . ?
O1 Fe1 N3 89.53(8) . . ?
N6 Fe1 N3 174.92(8) 1_455 . ?

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
O1 C1 C2 C3 -5.0(4) . . . . ?
C13 C1 C2 C3 172.9(2) . . . . ?
O1 C1 C2 C14 177.3(2) . . . . ?
C13 C1 C2 C14 -4.8(4) . . . . ?
C1 C2 C3 N1 0.3(4) . . . . ?
C14 C2 C3 N1 178.0(2) . . . . ?
C9 C4 C5 C6 -0.6(4) . . . . ?
N1 C4 C5 C6 -179.9(2) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 C4 -1.0(4) . . . . ?
C7 C8 C9 N2 177.6(2) . . . . ?
C5 C4 C9 C8 1.3(4) . . . . ?
N1 C4 C9 C8 -179.3(2) . . . . ?
C5 C4 C9 N2 -177.4(2) . . . . ?
N1 C4 C9 N2 2.0(3) . . . . ?
N2 C10 C11 C12 -3.0(4) . . . . ?
N2 C10 C11 C17 178.1(2) . . . . ?
C10 C11 C12 O2 4.8(4) . . . . ?
C17 C11 C12 O2 -176.4(2) . . . . ?
C10 C11 C12 C16 -173.7(2) . . . . ?
C17 C11 C12 C16 5.1(4) . . . . ?
C3 C2 C14 O3 -176.1(3) . . . . ?
C1 C2 C14 O3 1.7(4) . . . . ?
C3 C2 C14 O4 5.2(3) . . . . ?
C1 C2 C14 O4 -177.0(2) . . . . ?
C10 C11 C17 O5 4.9(4) . . . . ?
C12 C11 C17 O5 -174.0(2) . . . . ?
C10 C11 C17 O6 -173.7(2) . . . . ?
C12 C11 C17 O6 7.4(4) . . . . ?
N3 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C23 0.9(4) . . . . ?
C20 C21 C22 N4 -178.5(2) . . . . ?
C21 C22 C23 N3 -0.8(4) . . . . ?
N4 C22 C23 N3 178.6(2) . . . . ?
N6 C24 C25 C26 0.6(4) . . . . ?
N6 C24 C25 N5 -179.6(2) . . . . ?
C24 C25 C26 C27 -1.5(4) . . . . ?
N5 C25 C26 C27 178.7(2) . . . . ?
C25 C26 C27 C28 1.2(4) . . . . ?
C26 C27 C28 N6 0.0(4) . . . . ?
C2 C3 N1 C4 -178.2(2) . . . . ?
C2 C3 N1 Fe1 3.0(4) . . . . ?
C5 C4 N1 C3 -0.4(4) . . . . ?
C9 C4 N1 C3 -179.6(2) . . . . ?
C5 C4 N1 Fe1 178.6(2) . . . . ?
C9 C4 N1 Fe1 -0.7(3) . . . . ?
C11 C10 N2 C9 -178.3(2) . . . . ?
C11 C10 N2 Fe1 -4.1(4) . . . . ?
C8 C9 N2 C10 -6.1(4) . . . . ?
C4 C9 N2 C10 172.5(2) . . . . ?
C8 C9 N2 Fe1 179.1(2) . . . . ?
C4 C9 N2 Fe1 -2.3(3) . . . . ?
C22 C23 N3 C19 0.3(3) . . . . ?
C22 C23 N3 Fe1 -179.29(18) . . . . ?
C20 C19 N3 C23 0.1(3) . . . . ?
C20 C19 N3 Fe1 179.62(18) . . . . ?
C23 C22 N4 N5 -2.9(3) . . . . ?
C21 C22 N4 N5 176.4(2) . . . . ?
C22 N4 N5 C25 -179.9(2) . . . . ?
C26 C25 N5 N4 -178.5(2) . . . . ?
C24 C25 N5 N4 1.8(4) . . . . ?
C25 C24 N6 C28 0.6(3) . . . . ?
C25 C24 N6 Fe1 -179.15(18) . . . 1_655 ?
C27 C28 N6 C24 -0.9(4) . . . . ?
C27 C28 N6 Fe1 178.82(19) . . . 1_655 ?
C2 C1 O1 Fe1 6.0(3) . . . . ?
C13 C1 O1 Fe1 -172.05(17) . . . . ?
C11 C12 O2 Fe1 0.6(3) . . . . ?
C16 C12 O2 Fe1 179.23(16) . . . . ?
O3 C14 O4 C15 2.5(3) . . . . ?
C2 C14 O4 C15 -178.7(2) . . . . ?
O5 C17 O6 C18 4.5(5) . . . . ?
C11 C17 O6 C18 -176.8(3) . . . . ?
C10 N2 Fe1 N1 -173.0(2) . . . . ?
C9 N2 Fe1 N1 1.56(16) . . . . ?
C10 N2 Fe1 O2 6.8(2) . . . . ?
C9 N2 Fe1 O2 -178.61(15) . . . . ?
C10 N2 Fe1 N6 94.8(2) . . . 1_455 ?
C9 N2 Fe1 N6 -90.63(16) . . . 1_455 ?
C10 N2 Fe1 N3 -81.5(2) . . . . ?
C9 N2 Fe1 N3 93.06(16) . . . . ?

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
C16 H16A O2 0.98 2.65 3.567(3) 156.6 2_667
C19 H19 O3 0.95 2.65 3.200(3) 117.7 2_657
C20 H20 O3 0.95 2.59 3.165(3) 119.2 2_657
C27 H27 O5 0.95 2.56 3.261(3) 131.1 2_766
C28 H28 O4 0.95 2.62 3.303(3) 128.8 2_756

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_cl019
_database_code_depnum_ccdc_archive 'CCDC 1053320'
_audit_update_record             
;
2015-03-11 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT019_cl019               
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.933 Why ? 
RESPONSE: Weakly diffracting crystal
;
_audit_creation_date             2014-02-21
_audit_creation_method           SHELXL-2013

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '[FeL5b(azpy)].0,5azpy'
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H30 Fe N8 O4'
_chemical_formula_sum            'C33 H30 Fe N8 O4'
_chemical_formula_weight         658.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   17.134(2)
_cell_length_b                   16.762(2)
_cell_length_c                   21.725(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.206(15)
_cell_angle_gamma                90
_cell_volume                     6239(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    12580
_cell_measurement_theta_min      1.699
_cell_measurement_theta_max      24.648

_exptl_crystal_description       platelet-like
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             2736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'image-plate area detector'
_diffrn_measurement_device_type  STOE-IPDSII
_diffrn_measurement_method       Omega-Scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            35072
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_av_R_equivalents  0.1173
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.699
_diffrn_reflns_theta_max         24.648
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.921
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.921
_reflns_number_total             5205
_reflns_number_gt                3475
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²] 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         5205
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_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
C1 C 0.7923(2) 0.88201(19) 0.41882(15) 0.0436(8) Uani 1 1 d . . . . .
C2 C 0.8360(2) 0.95119(19) 0.40298(14) 0.0445(8) Uani 1 1 d . . . . .
C3 C 0.8585(2) 1.0089(2) 0.44744(15) 0.0470(8) Uani 1 1 d . . . . .
H3 H 0.8911 1.0494 0.4335 0.056 Uiso 1 1 calc R U . . .
C4 C 0.8738(2) 1.06860(19) 0.54615(15) 0.0457(8) Uani 1 1 d . . . . .
C5 C 0.9402(2) 1.1129(2) 0.53294(18) 0.0584(10) Uani 1 1 d . . . . .
H5 H 0.9634 1.1083 0.4945 0.070 Uiso 1 1 calc R U . . .
C6 C 0.9723(2) 1.1640(2) 0.57628(18) 0.0645(11) Uani 1 1 d . . . . .
H6 H 1.0156 1.1946 0.5662 0.077 Uiso 1 1 calc R U . . .
C7 C 0.9403(2) 1.1696(2) 0.63425(18) 0.0619(11) Uani 1 1 d . . . . .
H7 H 0.9630 1.2029 0.6635 0.074 Uiso 1 1 calc R U . . .
C8 C 0.8749(2) 1.1260(2) 0.64893(16) 0.0518(9) Uani 1 1 d . . . . .
H8 H 0.8540 1.1297 0.6883 0.062 Uiso 1 1 calc R U . . .
C9 C 0.8393(2) 1.07577(18) 0.60509(15) 0.0445(8) Uani 1 1 d . . . . .
C10 C 0.7300(2) 1.03934(19) 0.66519(15) 0.0446(8) Uani 1 1 d . . . . .
H10 H 0.7417 1.0844 0.6884 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6680(2) 0.99155(19) 0.68693(14) 0.0430(8) Uani 1 1 d . . . . .
C12 C 0.64448(19) 0.91913(18) 0.65743(15) 0.0410(8) Uani 1 1 d . . . . .
C13 C 0.7868(2) 0.8089(2) 0.37778(16) 0.0544(9) Uani 1 1 d . . . . .
H13A H 0.7888 0.7616 0.4027 0.082 Uiso 1 1 calc R U . . .
H13B H 0.8297 0.8087 0.3494 0.082 Uiso 1 1 calc R U . . .
H13C H 0.7385 0.8101 0.3553 0.082 Uiso 1 1 calc R U . . .
C14 C 0.8629(2) 0.9628(2) 0.33930(17) 0.0582(10) Uani 1 1 d . . . . .
C15 C 0.9329(3) 1.0149(3) 0.32686(18) 0.0762(13) Uani 1 1 d . . . . .
H15A H 0.9453 1.0130 0.2838 0.114 Uiso 1 1 calc R U . . .
H15B H 0.9767 0.9959 0.3504 0.114 Uiso 1 1 calc R U . . .
H15C H 0.9214 1.0689 0.3385 0.114 Uiso 1 1 calc R U . . .
C16 C 0.5837(2) 0.8640(2) 0.68337(16) 0.0491(9) Uani 1 1 d . . . . .
H16A H 0.5702 0.8245 0.6531 0.074 Uiso 1 1 calc R U . . .
H16B H 0.5381 0.8941 0.6941 0.074 Uiso 1 1 calc R U . . .
H16C H 0.6041 0.8381 0.7194 0.074 Uiso 1 1 calc R U . . .
C17 C 0.6278(2) 1.0191(2) 0.74296(16) 0.0496(9) Uani 1 1 d . . . . .
C18 C 0.6350(3) 1.1048(3) 0.7622(2) 0.0826(14) Uani 1 1 d . . . . .
H18A H 0.5980 1.1159 0.7942 0.124 Uiso 1 1 calc R U . . .
H18B H 0.6247 1.1387 0.7275 0.124 Uiso 1 1 calc R U . . .
H18C H 0.6868 1.1145 0.7773 0.124 Uiso 1 1 calc R U . . .
C19 C 0.8635(2) 0.86881(19) 0.65132(15) 0.0458(8) Uani 1 1 d . . . . .
H19 H 0.8405 0.9087 0.6748 0.055 Uiso 1 1 calc R U . . .
C20 C 0.9185(2) 0.8195(2) 0.67933(16) 0.0501(9) Uani 1 1 d . . . . .
H20 H 0.9303 0.8251 0.7209 0.060 Uiso 1 1 calc R U . . .
C21 C 0.9549(2) 0.7622(2) 0.64442(15) 0.0465(8) Uani 1 1 d . . . . .
H21 H 0.9932 0.7296 0.6615 0.056 Uiso 1 1 calc R U . . .
C22 C 0.93311(19) 0.75415(18) 0.58308(15) 0.0416(8) Uani 1 1 d . . . . .
C23 C 0.8762(2) 0.80442(19) 0.55957(16) 0.0439(8) Uani 1 1 d . . . . .
H23 H 0.8610 0.7977 0.5188 0.053 Uiso 1 1 calc R U . . .
C24 C 0.6252(2) 0.99658(19) 0.44498(15) 0.0456(8) Uani 1 1 d . . . . .
H24 H 0.6511 0.9601 0.4200 0.055 Uiso 1 1 calc R U . . .
C25 C 0.5598(2) 1.03435(19) 0.42145(15) 0.0460(8) Uani 1 1 d . . . . .
H25 H 0.5425 1.0233 0.3817 0.055 Uiso 1 1 calc R U . . .
C26 C 0.5206(2) 1.08872(19) 0.45782(15) 0.0441(8) Uani 1 1 d . . . . .
H26 H 0.4760 1.1145 0.4436 0.053 Uiso 1 1 calc R U . . .
C27 C 0.55048(19) 1.10358(18) 0.51666(14) 0.0418(8) Uani 1 1 d . . . . .
C28 C 0.61608(18) 1.06269(18) 0.53623(15) 0.0418(8) Uani 1 1 d . . . . .
H28 H 0.6350 1.0729 0.5756 0.050 Uiso 1 1 calc R U . . .
C51 C 0.7664(3) 0.8342(3) 0.8063(2) 0.0722(12) Uani 1 1 d . . . . .
H51 H 0.7650 0.8535 0.7662 0.087 Uiso 1 1 calc R U . . .
C52 C 0.7025(3) 0.8461(3) 0.84265(19) 0.0716(12) Uani 1 1 d . . . . .
H52 H 0.6593 0.8735 0.8276 0.086 Uiso 1 1 calc R U . . .
C53 C 0.7030(2) 0.8170(2) 0.90175(18) 0.0648(11) Uani 1 1 d . . . . .
H53 H 0.6601 0.8242 0.9273 0.078 Uiso 1 1 calc R U . . .
C54 C 0.7683(2) 0.7771(2) 0.92234(16) 0.0498(9) Uani 1 1 d . . . . .
C55 C 0.8290(3) 0.7691(3) 0.88290(19) 0.0771(13) Uani 1 1 d . . . . .
H55 H 0.8731 0.7424 0.8972 0.093 Uiso 1 1 calc R U . . .
Fe1 Fe 0.75280(3) 0.94186(3) 0.54713(2) 0.04040(15) Uani 1 1 d . . . . .
N1 N 0.83903(16) 1.01220(15) 0.50545(12) 0.0421(7) Uani 1 1 d . . . . .
N2 N 0.77301(16) 1.02777(15) 0.61628(12) 0.0408(6) Uani 1 1 d . . . . .
N3 N 0.84214(16) 0.86166(15) 0.59208(12) 0.0429(7) Uani 1 1 d . . . . .
N4 N 0.96356(16) 0.69852(16) 0.53995(12) 0.0457(7) Uani 1 1 d . . . . .
N5 N 0.51841(16) 1.15745(16) 0.56037(12) 0.0449(7) Uani 1 1 d . . . . .
N6 N 0.65358(16) 1.00958(15) 0.50184(12) 0.0437(7) Uani 1 1 d . . . . .
N51 N 0.8304(2) 0.7965(3) 0.82511(17) 0.0897(12) Uani 1 1 d . . . . .
N52 N 0.77753(17) 0.74314(18) 0.98217(13) 0.0534(8) Uani 1 1 d . . . . .
O1 O 0.75950(13) 0.87349(12) 0.47080(10) 0.0429(5) Uani 1 1 d . . . . .
O2 O 0.67303(13) 0.89708(12) 0.60629(10) 0.0436(5) Uani 1 1 d . . . . .
O3 O 0.83012(18) 0.93161(17) 0.29496(12) 0.0750(8) Uani 1 1 d . . . . .
O4 O 0.58738(16) 0.97593(16) 0.77511(11) 0.0616(7) 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
C1 O1 1.271(4) . ?
C1 C2 1.424(5) . ?
C1 C13 1.519(4) . ?
C2 C3 1.419(5) . ?
C2 C14 1.472(5) . ?
C3 N1 1.306(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(5) . ?
C4 C9 1.417(5) . ?
C4 N1 1.423(4) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.408(5) . ?
C8 H8 0.9300 . ?
C9 N2 1.414(4) . ?
C10 N2 1.310(4) . ?
C10 C11 1.413(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.430(5) . ?
C11 C17 1.475(5) . ?
C12 O2 1.271(4) . ?
C12 C16 1.503(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O3 1.229(4) . ?
C14 C15 1.510(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O4 1.222(4) . ?
C17 C18 1.502(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N3 1.342(4) . ?
C19 C20 1.392(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.389(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(4) . ?
C22 N4 1.422(4) . ?
C23 N3 1.328(4) . ?
C23 H23 0.9300 . ?
C24 N6 1.344(4) . ?
C24 C25 1.383(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.398(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.382(4) . ?
C27 N5 1.422(4) . ?
C28 N6 1.329(4) . ?
C28 H28 0.9300 . ?
C51 N51 1.328(5) . ?
C51 C52 1.367(6) . ?
C51 H51 0.9300 . ?
C52 C53 1.373(5) . ?
C52 H52 0.9300 . ?
C53 C54 1.378(5) . ?
C53 H53 0.9300 . ?
C54 C55 1.356(5) . ?
C54 N52 1.427(4) . ?
C55 N51 1.338(5) . ?
C55 H55 0.9300 . ?
Fe1 O1 2.019(2) . ?
Fe1 O2 2.024(2) . ?
Fe1 N1 2.098(3) . ?
Fe1 N2 2.109(3) . ?
Fe1 N3 2.257(3) . ?
Fe1 N6 2.266(3) . ?
N4 N5 1.245(3) 3_545 ?
N5 N4 1.245(3) 3_455 ?
N52 N52 1.244(6) 7_667 ?

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 C1 C2 122.8(3) . . ?
O1 C1 C13 113.9(3) . . ?
C2 C1 C13 123.1(3) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 C14 117.7(3) . . ?
C1 C2 C14 120.1(3) . . ?
N1 C3 C2 128.1(3) . . ?
N1 C3 H3 116.0 . . ?
C2 C3 H3 116.0 . . ?
C5 C4 C9 119.0(3) . . ?
C5 C4 N1 124.6(3) . . ?
C9 C4 N1 116.3(3) . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 N2 124.7(3) . . ?
C8 C9 C4 118.8(3) . . ?
N2 C9 C4 116.4(3) . . ?
N2 C10 C11 127.8(3) . . ?
N2 C10 H10 116.1 . . ?
C11 C10 H10 116.1 . . ?
C10 C11 C12 122.9(3) . . ?
C10 C11 C17 116.9(3) . . ?
C12 C11 C17 120.2(3) . . ?
O2 C12 C11 122.0(3) . . ?
O2 C12 C16 114.7(3) . . ?
C11 C12 C16 123.3(3) . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 C2 122.5(4) . . ?
O3 C14 C15 117.8(3) . . ?
C2 C14 C15 119.7(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C11 123.7(3) . . ?
O4 C17 C18 116.9(3) . . ?
C11 C17 C18 119.4(3) . . ?
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 . . ?
N3 C19 C20 123.2(3) . . ?
N3 C19 H19 118.4 . . ?
C20 C19 H19 118.4 . . ?
C21 C20 C19 118.8(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 118.4(3) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C23 C22 C21 118.8(3) . . ?
C23 C22 N4 114.5(3) . . ?
C21 C22 N4 126.7(3) . . ?
N3 C23 C22 123.6(3) . . ?
N3 C23 H23 118.2 . . ?
C22 C23 H23 118.2 . . ?
N6 C24 C25 123.7(3) . . ?
N6 C24 H24 118.1 . . ?
C25 C24 H24 118.1 . . ?
C26 C25 C24 119.0(3) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C27 117.6(3) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
C28 C27 C26 119.2(3) . . ?
C28 C27 N5 115.2(3) . . ?
C26 C27 N5 125.7(3) . . ?
N6 C28 C27 123.6(3) . . ?
N6 C28 H28 118.2 . . ?
C27 C28 H28 118.2 . . ?
N51 C51 C52 123.6(4) . . ?
N51 C51 H51 118.2 . . ?
C52 C51 H51 118.2 . . ?
C51 C52 C53 119.1(4) . . ?
C51 C52 H52 120.4 . . ?
C53 C52 H52 120.4 . . ?
C52 C53 C54 118.5(4) . . ?
C52 C53 H53 120.7 . . ?
C54 C53 H53 120.7 . . ?
C55 C54 C53 117.8(4) . . ?
C55 C54 N52 117.0(3) . . ?
C53 C54 N52 125.2(3) . . ?
N51 C55 C54 125.1(4) . . ?
N51 C55 H55 117.4 . . ?
C54 C55 H55 117.4 . . ?
O1 Fe1 O2 110.58(9) . . ?
O1 Fe1 N1 85.55(10) . . ?
O2 Fe1 N1 163.87(10) . . ?
O1 Fe1 N2 164.35(10) . . ?
O2 Fe1 N2 84.86(10) . . ?
N1 Fe1 N2 79.03(11) . . ?
O1 Fe1 N3 88.67(9) . . ?
O2 Fe1 N3 87.87(9) . . ?
N1 Fe1 N3 92.51(10) . . ?
N2 Fe1 N3 89.38(10) . . ?
O1 Fe1 N6 88.42(9) . . ?
O2 Fe1 N6 87.38(9) . . ?
N1 Fe1 N6 93.41(10) . . ?
N2 Fe1 N6 95.06(10) . . ?
N3 Fe1 N6 173.18(10) . . ?
C3 N1 C4 121.3(3) . . ?
C3 N1 Fe1 125.1(2) . . ?
C4 N1 Fe1 113.5(2) . . ?
C10 N2 C9 120.7(3) . . ?
C10 N2 Fe1 126.0(2) . . ?
C9 N2 Fe1 113.3(2) . . ?
C23 N3 C19 117.1(3) . . ?
C23 N3 Fe1 119.9(2) . . ?
C19 N3 Fe1 123.0(2) . . ?
N5 N4 C22 113.9(3) 3_545 . ?
N4 N5 C27 113.9(3) 3_455 . ?
C28 N6 C24 116.8(3) . . ?
C28 N6 Fe1 117.1(2) . . ?
C24 N6 Fe1 125.9(2) . . ?
C51 N51 C55 115.8(4) . . ?
N52 N52 C54 114.3(4) 7_667 . ?
C1 O1 Fe1 133.8(2) . . ?
C12 O2 Fe1 135.3(2) . . ?

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
O1 C1 C2 C3 11.9(5) . . . . ?
C13 C1 C2 C3 -162.2(3) . . . . ?
O1 C1 C2 C14 -171.1(3) . . . . ?
C13 C1 C2 C14 14.8(5) . . . . ?
C1 C2 C3 N1 -5.8(5) . . . . ?
C14 C2 C3 N1 177.1(3) . . . . ?
C9 C4 C5 C6 -0.5(5) . . . . ?
N1 C4 C5 C6 -177.0(3) . . . . ?
C4 C5 C6 C7 2.3(6) . . . . ?
C5 C6 C7 C8 -1.7(6) . . . . ?
C6 C7 C8 C9 -0.6(6) . . . . ?
C7 C8 C9 N2 178.8(3) . . . . ?
C7 C8 C9 C4 2.3(5) . . . . ?
C5 C4 C9 C8 -1.8(5) . . . . ?
N1 C4 C9 C8 175.0(3) . . . . ?
C5 C4 C9 N2 -178.5(3) . . . . ?
N1 C4 C9 N2 -1.7(4) . . . . ?
N2 C10 C11 C12 1.9(5) . . . . ?
N2 C10 C11 C17 -178.8(3) . . . . ?
C10 C11 C12 O2 -6.9(5) . . . . ?
C17 C11 C12 O2 173.7(3) . . . . ?
C10 C11 C12 C16 174.1(3) . . . . ?
C17 C11 C12 C16 -5.2(5) . . . . ?
C3 C2 C14 O3 -158.5(4) . . . . ?
C1 C2 C14 O3 24.4(5) . . . . ?
C3 C2 C14 C15 21.3(5) . . . . ?
C1 C2 C14 C15 -155.9(3) . . . . ?
C10 C11 C17 O4 -161.4(3) . . . . ?
C12 C11 C17 O4 18.0(5) . . . . ?
C10 C11 C17 C18 19.3(5) . . . . ?
C12 C11 C17 C18 -161.3(3) . . . . ?
N3 C19 C20 C21 2.3(5) . . . . ?
C19 C20 C21 C22 -2.3(5) . . . . ?
C20 C21 C22 C23 0.5(5) . . . . ?
C20 C21 C22 N4 -179.7(3) . . . . ?
C21 C22 C23 N3 1.6(5) . . . . ?
N4 C22 C23 N3 -178.2(3) . . . . ?
N6 C24 C25 C26 0.0(5) . . . . ?
C24 C25 C26 C27 1.1(5) . . . . ?
C25 C26 C27 C28 -1.3(5) . . . . ?
C25 C26 C27 N5 179.8(3) . . . . ?
C26 C27 C28 N6 0.5(5) . . . . ?
N5 C27 C28 N6 179.5(3) . . . . ?
N51 C51 C52 C53 -0.9(7) . . . . ?
C51 C52 C53 C54 0.3(6) . . . . ?
C52 C53 C54 C55 0.3(6) . . . . ?
C52 C53 C54 N52 -179.6(4) . . . . ?
C53 C54 C55 N51 -0.4(7) . . . . ?
N52 C54 C55 N51 179.5(4) . . . . ?
C2 C3 N1 C4 172.4(3) . . . . ?
C2 C3 N1 Fe1 -10.6(5) . . . . ?
C5 C4 N1 C3 -13.5(5) . . . . ?
C9 C4 N1 C3 169.9(3) . . . . ?
C5 C4 N1 Fe1 169.2(3) . . . . ?
C9 C4 N1 Fe1 -7.5(4) . . . . ?
C11 C10 N2 C9 -171.9(3) . . . . ?
C11 C10 N2 Fe1 9.2(5) . . . . ?
C8 C9 N2 C10 14.4(5) . . . . ?
C4 C9 N2 C10 -169.0(3) . . . . ?
C8 C9 N2 Fe1 -166.6(3) . . . . ?
C4 C9 N2 Fe1 10.0(3) . . . . ?
C22 C23 N3 C19 -1.7(5) . . . . ?
C22 C23 N3 Fe1 178.1(3) . . . . ?
C20 C19 N3 C23 -0.3(5) . . . . ?
C20 C19 N3 Fe1 179.9(3) . . . . ?
C23 C22 N4 N5 175.3(3) . . . 3_545 ?
C21 C22 N4 N5 -4.6(5) . . . 3_545 ?
C28 C27 N5 N4 174.1(3) . . . 3_455 ?
C26 C27 N5 N4 -6.9(5) . . . 3_455 ?
C27 C28 N6 C24 0.5(5) . . . . ?
C27 C28 N6 Fe1 -174.4(2) . . . . ?
C25 C24 N6 C28 -0.8(5) . . . . ?
C25 C24 N6 Fe1 173.7(2) . . . . ?
C52 C51 N51 C55 0.8(7) . . . . ?
C54 C55 N51 C51 -0.1(7) . . . . ?
C55 C54 N52 N52 175.4(4) . . . 7_667 ?
C53 C54 N52 N52 -4.7(6) . . . 7_667 ?
C2 C1 O1 Fe1 -0.2(5) . . . . ?
C13 C1 O1 Fe1 174.4(2) . . . . ?
C11 C12 O2 Fe1 -0.2(5) . . . . ?
C16 C12 O2 Fe1 178.9(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
C8 H8 O3 0.93 2.57 3.406(4) 149.9 6_576
C16 H16B O4 0.96 2.64 3.598(5) 179.3 2_656
C18 H18C O3 0.96 2.60 3.470(6) 150.7 6_576
C19 H19 N2 0.93 2.63 3.174(4) 117.8 .
C23 H23 O1 0.93 2.39 3.005(4) 123.5 .
C24 H24 O1 0.93 2.60 3.139(4) 117.4 .
C25 H25 O4 0.93 2.44 3.220(4) 141.1 6_575
C28 H28 N2 0.93 2.63 3.250(4) 124.5 .
C52 H52 O4 0.93 2.40 3.280(5) 158.1 .
C55 H55 N5 0.93 2.51 3.440(5) 173.3 4_646
C8 H8 O3 0.93 2.57 3.406(4) 149.9 6_576
C16 H16B O4 0.96 2.64 3.598(5) 179.3 2_656
C18 H18C O3 0.96 2.60 3.470(6) 150.7 6_576
C19 H19 N2 0.93 2.63 3.174(4) 117.8 .
C23 H23 O1 0.93 2.39 3.005(4) 123.5 .
C24 H24 O1 0.93 2.60 3.139(4) 117.4 .
C25 H25 O4 0.93 2.44 3.220(4) 141.1 6_575
C28 H28 N2 0.93 2.63 3.250(4) 124.5 .
C52 H52 O4 0.93 2.40 3.280(5) 158.1 .
C55 H55 N5 0.93 2.51 3.440(5) 173.3 4_646

_refine_diff_density_max         0.512
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.065


