# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_trl140314_a_sqr
_audit_block_doi                 10.5517/cc1k2571
_database_code_depnum_ccdc_archive 'CCDC 1432052'
_audit_update_record             
;
2015-10-19 deposited with the CCDC.
2016-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H39 Cl2 Fe N5 O9'
_chemical_formula_weight         764.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8220(19)
_cell_length_b                   22.135(4)
_cell_length_c                   17.435(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.161(6)
_cell_angle_gamma                90.00
_cell_volume                     4011.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5223
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      19.56

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1592
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8067
_exptl_absorpt_correction_T_max  0.8960
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36034
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.96
_reflns_number_total             5500
_reflns_number_gt                3646
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'ORTEP 3V2'

_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. 
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.015 0.000 0.000 381 117 ' '
2 0.012 0.500 0.500 381 116 ' '
_platon_squeeze_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5500
_refine_ls_number_parameters     448
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0993
_refine_ls_wR_factor_ref         0.2636
_refine_ls_wR_factor_gt          0.2539
_refine_ls_goodness_of_fit_ref   1.609
_refine_ls_restrained_S_all      1.592
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.77726(9) 0.66246(5) 0.20238(6) 0.0467(4) Uani 1 1 d U . .
Cl1 Cl 0.2060(2) 0.78584(11) 0.18773(16) 0.0747(7) Uani 1 1 d U . .
Cl2 Cl 0.2364(2) 0.53991(12) 0.27019(19) 0.0881(8) Uani 1 1 d U . .
O1 O 0.7075(4) 0.6421(2) 0.0916(3) 0.0476(12) Uani 1 1 d U . .
N4 N 0.6023(5) 0.6658(3) 0.2165(4) 0.0503(14) Uani 1 1 d U . .
N2 N 0.8398(5) 0.6826(3) 0.3153(4) 0.0479(14) Uani 1 1 d U . .
O2 O 0.3257(6) 0.8067(3) 0.2336(5) 0.099(2) Uani 1 1 d U . .
N3 N 0.7402(6) 0.7489(3) 0.1759(3) 0.0493(14) Uani 1 1 d U . .
N1 N 0.7662(5) 0.5782(3) 0.2346(4) 0.0480(14) Uani 1 1 d U . .
N5 N 0.9310(6) 0.6575(3) 0.1765(4) 0.0535(15) Uani 1 1 d U . .
H5 H 1.0037 0.6646 0.2109 0.064 Uiso 1 1 calc R . .
C19 C 0.7925(6) 0.6349(3) 0.0542(4) 0.0397(15) Uani 1 1 d U . .
O5 O 0.1143(7) 0.8343(3) 0.1669(6) 0.118(3) Uani 1 1 d U . .
C24 C 0.9226(6) 0.6422(3) 0.1001(4) 0.0413(16) Uani 1 1 d U . .
C23 C 1.0281(7) 0.6335(3) 0.0684(5) 0.0485(17) Uani 1 1 d U . .
H23 H 1.1122 0.6387 0.1000 0.058 Uiso 1 1 calc R . .
C20 C 0.7674(6) 0.6209(3) -0.0301(4) 0.0449(16) Uani 1 1 d U . .
C22 C 1.0029(7) 0.6173(3) -0.0096(5) 0.0483(17) Uani 1 1 d U . .
C21 C 0.8715(6) 0.6122(3) -0.0563(4) 0.0460(17) Uani 1 1 d U . .
H21 H 0.8569 0.6018 -0.1098 0.055 Uiso 1 1 calc R . .
C11 C 0.7485(7) 0.6883(3) 0.3521(5) 0.0514(17) Uani 1 1 d U . .
C29 C 1.1098(7) 0.6035(4) -0.0488(5) 0.0569(19) Uani 1 1 d U . .
C18 C 0.5291(6) 0.7129(4) 0.1602(5) 0.0582(19) Uani 1 1 d U . .
H18A H 0.4960 0.6958 0.1072 0.070 Uiso 1 1 calc R . .
H18B H 0.4569 0.7271 0.1781 0.070 Uiso 1 1 calc R . .
C25 C 0.6277(6) 0.6148(3) -0.0813(4) 0.0502(18) Uani 1 1 d U . .
C5 C 0.6472(7) 0.5612(4) 0.2333(5) 0.0574(19) Uani 1 1 d U . .
C17 C 0.6149(7) 0.7629(4) 0.1580(4) 0.0512(17) Uani 1 1 d U . .
O6 O 0.1752(7) 0.5921(4) 0.2852(7) 0.149(4) Uani 1 1 d U . .
C13 C 0.8271(8) 0.7918(4) 0.1762(5) 0.0570(19) Uani 1 1 d U . .
H13 H 0.9139 0.7818 0.1888 0.068 Uiso 1 1 calc R . .
C26 C 0.5678(8) 0.5584(4) -0.0578(5) 0.070(2) Uani 1 1 d U . .
H26A H 0.6114 0.5234 -0.0697 0.105 Uiso 1 1 calc R . .
H26B H 0.4785 0.5566 -0.0872 0.105 Uiso 1 1 calc R . .
H26C H 0.5754 0.5595 -0.0016 0.105 Uiso 1 1 calc R . .
O9 O 0.3608(7) 0.5339(4) 0.3198(6) 0.147(3) Uani 1 1 d U . .
C2 C 0.8467(9) 0.4816(4) 0.2841(6) 0.076(2) Uani 1 1 d U . .
H2 H 0.9162 0.4555 0.3017 0.091 Uiso 1 1 calc R . .
O3 O 0.2201(9) 0.7591(5) 0.1167(6) 0.162(4) Uani 1 1 d U . .
C15 C 0.6635(10) 0.8648(4) 0.1389(6) 0.079(3) Uani 1 1 d U . .
H15 H 0.6376 0.9044 0.1256 0.095 Uiso 1 1 calc R . .
C1 C 0.8646(8) 0.5405(4) 0.2586(5) 0.066(2) Uani 1 1 d U . .
H1 H 0.9465 0.5531 0.2585 0.079 Uiso 1 1 calc R . .
C4 C 0.6268(8) 0.5039(4) 0.2601(6) 0.074(2) Uani 1 1 d U . .
H4 H 0.5454 0.4926 0.2630 0.089 Uiso 1 1 calc R . .
C30 C 1.0884(10) 0.6396(5) -0.1274(6) 0.088(3) Uani 1 1 d U . .
H30A H 1.1540 0.6293 -0.1525 0.133 Uiso 1 1 calc R . .
H30B H 1.0924 0.6821 -0.1159 0.133 Uiso 1 1 calc R . .
H30C H 1.0055 0.6299 -0.1626 0.133 Uiso 1 1 calc R . .
C6 C 0.5441(7) 0.6050(4) 0.2004(6) 0.064(2) Uani 1 1 d U . .
H6A H 0.5087 0.5988 0.1434 0.077 Uiso 1 1 calc R . .
H6B H 0.4755 0.6004 0.2258 0.077 Uiso 1 1 calc R . .
C28 C 0.5461(7) 0.6690(4) -0.0723(6) 0.069(2) Uani 1 1 d U . .
H28A H 0.4587 0.6624 -0.1030 0.103 Uiso 1 1 calc R . .
H28B H 0.5788 0.7047 -0.0910 0.103 Uiso 1 1 calc R . .
H28C H 0.5494 0.6739 -0.0170 0.103 Uiso 1 1 calc R . .
O4 O 0.1557(9) 0.7437(4) 0.2309(6) 0.151(3) Uani 1 1 d U . .
C3 C 0.7288(9) 0.4640(4) 0.2825(6) 0.082(3) Uani 1 1 d U . .
H3 H 0.7147 0.4246 0.2966 0.099 Uiso 1 1 calc R . .
C7 C 0.9639(7) 0.6876(4) 0.3582(5) 0.061(2) Uani 1 1 d U . .
H7 H 1.0284 0.6830 0.3327 0.073 Uiso 1 1 calc R . .
C27 C 0.6245(8) 0.6110(4) -0.1693(5) 0.077(3) Uani 1 1 d U . .
H27A H 0.6668 0.5746 -0.1783 0.116 Uiso 1 1 calc R . .
H27B H 0.6679 0.6454 -0.1831 0.116 Uiso 1 1 calc R . .
H27C H 0.5368 0.6105 -0.2016 0.116 Uiso 1 1 calc R . .
C8 C 0.9973(9) 0.6994(4) 0.4396(6) 0.078(3) Uani 1 1 d U . .
H8 H 1.0831 0.7040 0.4685 0.094 Uiso 1 1 calc R . .
C32 C 1.2416(7) 0.6186(5) 0.0063(6) 0.088(3) Uani 1 1 d U . .
H32A H 1.2592 0.5931 0.0526 0.132 Uiso 1 1 calc R . .
H32B H 1.2433 0.6601 0.0224 0.132 Uiso 1 1 calc R . .
H32C H 1.3058 0.6121 -0.0214 0.132 Uiso 1 1 calc R . .
C12 C 0.6134(8) 0.6843(4) 0.3025(5) 0.069(2) Uani 1 1 d U . .
H12A H 0.5722 0.7232 0.3024 0.082 Uiso 1 1 calc R . .
H12B H 0.5679 0.6551 0.3260 0.082 Uiso 1 1 calc R . .
C31 C 1.1050(9) 0.5366(4) -0.0680(6) 0.077(2) Uani 1 1 d U . .
H31A H 1.1674 0.5274 -0.0960 0.116 Uiso 1 1 calc R . .
H31B H 1.0206 0.5262 -0.1008 0.116 Uiso 1 1 calc R . .
H31C H 1.1237 0.5137 -0.0193 0.116 Uiso 1 1 calc R . .
O7 O 0.1599(9) 0.4887(4) 0.2715(8) 0.171(4) Uani 1 1 d U . .
C14 C 0.7897(10) 0.8503(4) 0.1582(5) 0.076(2) Uani 1 1 d U . .
H14 H 0.8509 0.8800 0.1592 0.092 Uiso 1 1 calc R . .
C10 C 0.7757(9) 0.6972(4) 0.4335(5) 0.072(2) Uani 1 1 d U . .
H10 H 0.7102 0.6985 0.4585 0.086 Uiso 1 1 calc R . .
C16 C 0.5732(9) 0.8208(4) 0.1388(5) 0.073(2) Uani 1 1 d U . .
H16 H 0.4861 0.8302 0.1260 0.088 Uiso 1 1 calc R . .
O8 O 0.2499(11) 0.5408(5) 0.1902(7) 0.175(4) Uani 1 1 d U . .
C9 C 0.9008(10) 0.7042(4) 0.4763(6) 0.082(3) Uani 1 1 d U . .
H9 H 0.9211 0.7122 0.5307 0.099 Uiso 1 1 calc R . .


_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 N5 1.845(6) . ?
Fe1 O1 1.921(5) . ?
Fe1 N2 1.948(6) . ?
Fe1 N1 1.962(6) . ?
Fe1 N4 1.978(6) . ?
Fe1 N3 1.983(6) . ?
Cl1 O2 1.398(6) . ?
Cl1 O3 1.418(8) . ?
Cl1 O4 1.401(8) . ?
Cl1 O5 1.438(7) . ?
Cl2 O6 1.392(8) . ?
Cl2 O9 1.390(8) . ?
Cl2 O7 1.407(8) . ?
Cl2 O8 1.442(10) . ?
O1 C19 1.276(7) . ?
N4 C6 1.480(9) . ?
N4 C18 1.497(9) . ?
N4 C12 1.527(10) . ?
N2 C11 1.325(8) . ?
N2 C7 1.348(9) . ?
N3 C13 1.336(9) . ?
N3 C17 1.340(9) . ?
N1 C5 1.335(9) . ?
N1 C1 1.326(9) . ?
N5 C24 1.353(9) . ?
N5 H5 0.8600 . ?
C19 C24 1.422(9) . ?
C19 C20 1.452(10) . ?
C24 C23 1.413(9) . ?
C23 C22 1.359(10) . ?
C23 H23 0.9300 . ?
C20 C21 1.343(9) . ?
C20 C25 1.533(10) . ?
C22 C21 1.433(10) . ?
C22 C29 1.530(10) . ?
C21 H21 0.9300 . ?
C11 C10 1.381(11) . ?
C11 C12 1.480(11) . ?
C29 C31 1.516(11) . ?
C29 C32 1.519(11) . ?
C29 C30 1.548(12) . ?
C18 C17 1.452(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C25 C26 1.515(10) . ?
C25 C27 1.527(11) . ?
C25 C28 1.522(10) . ?
C5 C4 1.391(11) . ?
C5 C6 1.468(11) . ?
C17 C16 1.370(11) . ?
C13 C14 1.367(11) . ?
C13 H13 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C2 C3 1.327(12) . ?
C2 C1 1.408(12) . ?
C2 H2 0.9300 . ?
C15 C14 1.351(13) . ?
C15 C16 1.380(13) . ?
C15 H15 0.9300 . ?
C1 H1 0.9300 . ?
C4 C3 1.382(12) . ?
C4 H4 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C3 H3 0.9300 . ?
C7 C8 1.389(12) . ?
C7 H7 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C8 C9 1.372(12) . ?
C8 H8 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C14 H14 0.9300 . ?
C10 C9 1.360(12) . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C9 H9 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
N5 Fe1 O1 82.5(2) . . ?
N5 Fe1 N2 100.2(3) . . ?
O1 Fe1 N2 177.2(2) . . ?
N5 Fe1 N1 98.4(2) . . ?
O1 Fe1 N1 91.5(2) . . ?
N2 Fe1 N1 87.7(2) . . ?
N5 Fe1 N4 173.2(3) . . ?
O1 Fe1 N4 90.7(2) . . ?
N2 Fe1 N4 86.6(2) . . ?
N1 Fe1 N4 82.1(2) . . ?
N5 Fe1 N3 97.9(2) . . ?
O1 Fe1 N3 89.7(2) . . ?
N2 Fe1 N3 90.3(2) . . ?
N1 Fe1 N3 163.7(2) . . ?
N4 Fe1 N3 81.6(2) . . ?
O2 Cl1 O3 109.3(5) . . ?
O2 Cl1 O4 110.5(5) . . ?
O3 Cl1 O4 110.1(7) . . ?
O2 Cl1 O5 111.2(4) . . ?
O3 Cl1 O5 109.0(6) . . ?
O4 Cl1 O5 106.8(6) . . ?
O6 Cl2 O9 113.1(6) . . ?
O6 Cl2 O7 110.7(6) . . ?
O9 Cl2 O7 112.7(6) . . ?
O6 Cl2 O8 110.6(7) . . ?
O9 Cl2 O8 105.1(6) . . ?
O7 Cl2 O8 104.2(8) . . ?
C19 O1 Fe1 113.9(4) . . ?
C6 N4 C18 112.9(6) . . ?
C6 N4 C12 110.1(6) . . ?
C18 N4 C12 109.8(6) . . ?
C6 N4 Fe1 108.3(4) . . ?
C18 N4 Fe1 107.2(4) . . ?
C12 N4 Fe1 108.4(4) . . ?
C11 N2 C7 119.1(7) . . ?
C11 N2 Fe1 114.5(5) . . ?
C7 N2 Fe1 126.2(5) . . ?
C13 N3 C17 120.1(7) . . ?
C13 N3 Fe1 126.1(5) . . ?
C17 N3 Fe1 113.8(5) . . ?
C5 N1 C1 121.0(7) . . ?
C5 N1 Fe1 113.5(5) . . ?
C1 N1 Fe1 125.5(5) . . ?
C24 N5 Fe1 115.9(5) . . ?
C24 N5 H5 122.0 . . ?
Fe1 N5 H5 122.0 . . ?
O1 C19 C24 116.1(6) . . ?
O1 C19 C20 125.8(6) . . ?
C24 C19 C20 118.1(6) . . ?
N5 C24 C23 125.4(6) . . ?
N5 C24 C19 111.5(6) . . ?
C23 C24 C19 123.1(7) . . ?
C22 C23 C24 117.9(7) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C21 C20 C19 116.0(6) . . ?
C21 C20 C25 125.0(7) . . ?
C19 C20 C25 119.0(6) . . ?
C23 C22 C21 118.8(6) . . ?
C23 C22 C29 122.3(6) . . ?
C21 C22 C29 119.0(7) . . ?
C20 C21 C22 126.1(7) . . ?
C20 C21 H21 117.0 . . ?
C22 C21 H21 117.0 . . ?
N2 C11 C10 122.4(7) . . ?
N2 C11 C12 117.4(7) . . ?
C10 C11 C12 120.2(7) . . ?
C31 C29 C32 108.9(7) . . ?
C31 C29 C30 108.8(7) . . ?
C32 C29 C30 109.2(7) . . ?
C31 C29 C22 108.0(6) . . ?
C32 C29 C22 111.6(6) . . ?
C30 C29 C22 110.3(6) . . ?
C17 C18 N4 108.8(6) . . ?
C17 C18 H18A 109.9 . . ?
N4 C18 H18A 109.9 . . ?
C17 C18 H18B 109.9 . . ?
N4 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C26 C25 C27 109.5(7) . . ?
C26 C25 C20 110.0(6) . . ?
C27 C25 C20 109.4(6) . . ?
C26 C25 C28 108.4(6) . . ?
C27 C25 C28 107.2(7) . . ?
C20 C25 C28 112.1(6) . . ?
N1 C5 C4 119.6(7) . . ?
N1 C5 C6 116.5(7) . . ?
C4 C5 C6 123.9(7) . . ?
N3 C17 C16 121.1(7) . . ?
N3 C17 C18 115.5(7) . . ?
C16 C17 C18 123.3(7) . . ?
N3 C13 C14 120.6(8) . . ?
N3 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C3 C2 C1 118.7(9) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C14 C15 C16 119.9(9) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
N1 C1 C2 120.9(7) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C4 C5 119.2(8) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N4 C6 C5 106.8(6) . . ?
N4 C6 H6A 110.4 . . ?
C5 C6 H6A 110.4 . . ?
N4 C6 H6B 110.4 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C2 C3 C4 120.4(9) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
N2 C7 C8 121.2(7) . . ?
N2 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C9 C8 C7 118.4(8) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C11 C12 N4 112.6(6) . . ?
C11 C12 H12A 109.1 . . ?
N4 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
N4 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C15 C14 C13 119.8(9) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C9 C10 C11 118.3(8) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C15 C16 C17 118.4(9) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C10 C9 C8 120.5(9) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.96
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.172
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.144
####################################################################### 
# 
# 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_trl1509151
_audit_block_doi                 10.5517/ccdc.csd.cc1ky0tb
_database_code_depnum_ccdc_archive 'CCDC 1457862'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-04-19 downloaded from the CCDC.
;
_audit_creation_date             2016-03-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H22 Fe N5 O2, Cl O4'
_chemical_formula_sum            'C24 H22 Cl Fe N5 O6'
_chemical_formula_weight         567.77
_chemical_absolute_configuration ad
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.3918(5)
_cell_length_b                   15.3888(9)
_cell_length_c                   9.8617(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8654(15)
_cell_angle_gamma                90.00
_cell_volume                     1254.71(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4223
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.131
_cell_measurement_theta_min      2.46
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0832 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.8775.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17687
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.36
_diffrn_reflns_theta_min         2.10
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                5207
_reflns_number_total             6416
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(12)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6416
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0256P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0753
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C4(H4), C8(H8), C7(H7), C2(H2), C11(H11), C5(H5), C10(H10),
 C14(H14), C15(H15), C16(H16), C21(H21), C20(H20), C19(H19), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Fe1 Fe 0.97289(4) 0.74851(2) 0.64309(3) 0.01871(8) Uani 1 d . . .
N2 N 1.0135(3) 0.89272(14) 0.6415(2) 0.0189(5) Uani 1 d . . .
O2 O 0.9701(2) 0.61712(12) 0.63318(18) 0.0259(5) Uani 1 d . . .
C6 C 0.7671(3) 0.7560(2) 0.1963(2) 0.0304(6) Uani 1 d . . .
H6 H 0.7371 0.7144 0.1252 0.036 Uiso 1 calc . . R
Cl1 Cl 0.44622(8) 0.51460(4) 0.15577(7) 0.02686(15) Uani 1 d . . .
C9 C 1.1770(3) 0.7475(2) 1.0888(2) 0.0356(6) Uani 1 d . . .
H9 H 1.2184 0.7051 1.1557 0.043 Uiso 1 calc . . R
C4 C 0.8009(3) 0.90261(19) 0.2756(3) 0.0291(6) Uani 1 d . . .
H4 H 0.7950 0.9634 0.2591 0.035 Uiso 1 calc . . R
C8 C 1.1108(4) 0.89371(19) 1.0243(3) 0.0326(7) Uani 1 d . . .
H8 H 1.1063 0.9536 1.0468 0.039 Uiso 1 calc . . R
C7 C 0.8244(3) 0.72934(16) 0.3297(3) 0.0252(6) Uani 1 d . . .
H7 H 0.8342 0.6688 0.3483 0.030 Uiso 1 calc . . R
C3 C 0.8948(3) 0.93144(16) 0.5283(2) 0.0220(5) Uani 1 d . . .
H3A H 0.9394 0.9864 0.4982 0.026 Uiso 1 calc . . R
H3B H 0.7940 0.9454 0.5632 0.026 Uiso 1 calc . . R
C2 C 1.3803(3) 0.84926(19) 0.4781(3) 0.0255(6) Uani 1 d . . .
H2 H 1.4178 0.9067 0.4678 0.031 Uiso 1 calc . . R
C11 C 1.1258(3) 0.72412(16) 0.9530(3) 0.0256(6) Uani 1 d . . .
H11 H 1.1312 0.6647 0.9281 0.031 Uiso 1 calc . . R
C5 C 0.7544(4) 0.84406(19) 0.1680(3) 0.0335(7) Uani 1 d . . .
H5 H 0.7148 0.8642 0.0774 0.040 Uiso 1 calc . . R
C1 C 1.2545(3) 0.83376(17) 0.5503(2) 0.0207(5) Uani 1 d . . .
C18 C 0.8557(3) 0.87089(17) 0.4063(3) 0.0215(5) Uani 1 d . . .
C10 C 1.1665(4) 0.8334(2) 1.1251(3) 0.0410(8) Uani 1 d . . .
H10 H 1.1972 0.8511 1.2182 0.049 Uiso 1 calc . . R
C13 C 1.0619(3) 0.86611(17) 0.8910(3) 0.0215(5) Uani 1 d . . .
C12 C 0.9918(3) 0.92792(16) 0.7769(2) 0.0234(6) Uani 1 d . . .
H12A H 0.8752 0.9366 0.7781 0.028 Uiso 1 calc . . R
H12B H 1.0463 0.9850 0.7920 0.028 Uiso 1 calc . . R
C14 C 1.2698(3) 0.6862(2) 0.5125(3) 0.0269(6) Uani 1 d . . .
H14 H 1.2316 0.6291 0.5246 0.032 Uiso 1 calc . . R
C17 C 1.1836(3) 0.90637(16) 0.6236(3) 0.0229(5) Uani 1 d . . .
H17A H 1.2510 0.9142 0.7155 0.027 Uiso 1 calc . . R
H17B H 1.1897 0.9608 0.5713 0.027 Uiso 1 calc . . R
C15 C 1.3941(3) 0.6965(2) 0.4405(3) 0.0323(7) Uani 1 d . . .
H15 H 1.4415 0.6476 0.4042 0.039 Uiso 1 calc . . R
C16 C 1.4497(3) 0.7799(2) 0.4216(3) 0.0315(7) Uani 1 d . . .
H16 H 1.5344 0.7890 0.3704 0.038 Uiso 1 calc . . R
N4 N 1.1989(2) 0.75331(16) 0.56702(18) 0.0215(4) Uani 1 d . . .
N3 N 1.0690(2) 0.78203(14) 0.8549(2) 0.0222(5) Uani 1 d . . .
N1 N 0.8668(2) 0.78541(13) 0.4343(2) 0.0201(5) Uani 1 d . . .
C21 C 0.5046(3) 0.64709(19) 0.8450(3) 0.0303(7) Uani 1 d . . .
H21 H 0.4216 0.6232 0.8882 0.036 Uiso 1 calc . . R
C22 C 0.7328(3) 0.62969(16) 0.7326(2) 0.0205(5) Uani 1 d . . .
C23 C 0.8573(3) 0.57511(16) 0.6783(2) 0.0222(6) Uani 1 d . . .
C20 C 0.5188(3) 0.7357(2) 0.8311(2) 0.0276(6) Uani 1 d . . .
H20 H 0.4462 0.7742 0.8651 0.033 Uiso 1 calc . . R
C19 C 0.6407(3) 0.76779(16) 0.7666(2) 0.0243(6) Uani 1 d . . .
H19 H 0.6488 0.8289 0.7558 0.029 Uiso 1 calc . . R
N5 N 0.7477(3) 0.71656(13) 0.7188(2) 0.0205(5) Uani 1 d . . .
O1 O 0.8442(2) 0.49541(12) 0.6792(2) 0.0340(5) Uani 1 d . . .
C24 C 0.6134(3) 0.59364(18) 0.7949(3) 0.0284(6) Uani 1 d . . .
H24 H 0.6059 0.5323 0.8034 0.034 Uiso 1 calc . . R
O3 O 0.4189(2) 0.48510(13) 0.28900(19) 0.0383(5) Uani 1 d . . .
O5 O 0.2943(3) 0.53258(15) 0.0692(2) 0.0495(6) Uani 1 d . . .
O6 O 0.5255(3) 0.44757(15) 0.0917(2) 0.0500(6) Uani 1 d . . .
O4 O 0.5434(3) 0.59071(16) 0.1730(2) 0.0630(8) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N2 2.246(2) . ?
Fe1 O2 2.0242(19) . ?
Fe1 N4 2.1571(19) . ?
Fe1 N3 2.169(2) . ?
Fe1 N1 2.174(2) . ?
Fe1 N5 2.203(2) . ?
N2 C3 1.487(3) . ?
N2 C12 1.481(3) . ?
N2 C17 1.483(3) . ?
O2 C23 1.287(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(4) . ?
C6 C5 1.385(5) . ?
Cl1 O3 1.4450(19) . ?
Cl1 O5 1.435(2) . ?
Cl1 O6 1.432(2) . ?
Cl1 O4 1.420(2) . ?
C9 H9 0.9500 . ?
C9 C11 1.382(4) . ?
C9 C10 1.377(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(4) . ?
C4 C18 1.382(3) . ?
C8 H8 0.9500 . ?
C8 C10 1.381(4) . ?
C8 C13 1.376(3) . ?
C7 H7 0.9500 . ?
C7 N1 1.345(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C18 1.513(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.392(4) . ?
C2 C16 1.378(4) . ?
C11 H11 0.9500 . ?
C11 N3 1.341(3) . ?
C5 H5 0.9500 . ?
C1 C17 1.507(3) . ?
C1 N4 1.343(3) . ?
C18 N1 1.344(3) . ?
C10 H10 0.9500 . ?
C13 C12 1.514(3) . ?
C13 N3 1.346(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14 0.9500 . ?
C14 C15 1.367(4) . ?
C14 N4 1.349(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C16 1.389(4) . ?
C16 H16 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.378(4) . ?
C21 C24 1.382(4) . ?
C22 C23 1.508(4) . ?
C22 N5 1.352(3) . ?
C22 C24 1.379(4) . ?
C23 O1 1.232(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.384(4) . ?
C19 H19 0.9500 . ?
C19 N5 1.340(3) . ?
C24 H24 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
O2 Fe1 N2 170.84(8) . . ?
O2 Fe1 N4 91.21(8) . . ?
O2 Fe1 N3 106.46(8) . . ?
O2 Fe1 N1 102.45(7) . . ?
O2 Fe1 N5 77.87(7) . . ?
N4 Fe1 N2 79.63(9) . . ?
N4 Fe1 N3 97.05(7) . . ?
N4 Fe1 N1 84.46(7) . . ?
N4 Fe1 N5 169.07(9) . . ?
N3 Fe1 N2 74.93(8) . . ?
N3 Fe1 N1 150.99(8) . . ?
N3 Fe1 N5 85.75(8) . . ?
N1 Fe1 N2 76.89(7) . . ?
N1 Fe1 N5 98.24(8) . . ?
N5 Fe1 N2 111.29(8) . . ?
C3 N2 Fe1 108.56(15) . . ?
C12 N2 Fe1 108.22(15) . . ?
C12 N2 C3 111.1(2) . . ?
C12 N2 C17 108.97(19) . . ?
C17 N2 Fe1 106.93(15) . . ?
C17 N2 C3 112.86(19) . . ?
C23 O2 Fe1 119.23(17) . . ?
C7 C6 H6 120.5 . . ?
C7 C6 C5 118.9(3) . . ?
C5 C6 H6 120.5 . . ?
O5 Cl1 O3 109.79(13) . . ?
O6 Cl1 O3 109.44(13) . . ?
O6 Cl1 O5 108.01(14) . . ?
O4 Cl1 O3 109.13(13) . . ?
O4 Cl1 O5 110.20(16) . . ?
O4 Cl1 O6 110.25(16) . . ?
C11 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C10 C9 C11 118.6(3) . . ?
C5 C4 H4 120.5 . . ?
C18 C4 H4 120.5 . . ?
C18 C4 C5 119.1(3) . . ?
C10 C8 H8 120.4 . . ?
C13 C8 H8 120.4 . . ?
C13 C8 C10 119.3(3) . . ?
C6 C7 H7 118.6 . . ?
N1 C7 C6 122.9(3) . . ?
N1 C7 H7 118.6 . . ?
N2 C3 H3A 109.2 . . ?
N2 C3 H3B 109.2 . . ?
N2 C3 C18 112.1(2) . . ?
H3A C3 H3B 107.9 . . ?
C18 C3 H3A 109.2 . . ?
C18 C3 H3B 109.2 . . ?
C1 C2 H2 120.5 . . ?
C16 C2 H2 120.5 . . ?
C16 C2 C1 118.9(3) . . ?
C9 C11 H11 118.7 . . ?
N3 C11 C9 122.6(3) . . ?
N3 C11 H11 118.7 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C2 C1 C17 121.0(2) . . ?
N4 C1 C2 122.0(2) . . ?
N4 C1 C17 116.8(2) . . ?
C4 C18 C3 121.1(2) . . ?
N1 C18 C4 122.5(2) . . ?
N1 C18 C3 116.2(2) . . ?
C9 C10 C8 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C8 C10 H10 120.4 . . ?
C8 C13 C12 122.1(2) . . ?
N3 C13 C8 122.0(2) . . ?
N3 C13 C12 115.9(2) . . ?
N2 C12 C13 110.4(2) . . ?
N2 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C15 C14 H14 118.5 . . ?
N4 C14 H14 118.5 . . ?
N4 C14 C15 123.1(3) . . ?
N2 C17 C1 114.8(2) . . ?
N2 C17 H17A 108.6 . . ?
N2 C17 H17B 108.6 . . ?
C1 C17 H17A 108.6 . . ?
C1 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.7(3) . . ?
C16 C15 H15 120.6 . . ?
C2 C16 C15 119.1(3) . . ?
C2 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C1 N4 Fe1 114.76(18) . . ?
C1 N4 C14 118.1(2) . . ?
C14 N4 Fe1 125.91(19) . . ?
C11 N3 Fe1 124.34(17) . . ?
C11 N3 C13 118.3(2) . . ?
C13 N3 Fe1 117.21(16) . . ?
C7 N1 Fe1 124.76(17) . . ?
C18 N1 Fe1 116.92(16) . . ?
C18 N1 C7 118.1(2) . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C24 118.7(3) . . ?
C24 C21 H21 120.7 . . ?
N5 C22 C23 115.7(2) . . ?
N5 C22 C24 122.0(2) . . ?
C24 C22 C23 122.3(2) . . ?
O2 C23 C22 116.0(2) . . ?
O1 C23 O2 125.1(3) . . ?
O1 C23 C22 119.0(2) . . ?
C21 C20 H20 120.6 . . ?
C21 C20 C19 118.8(3) . . ?
C19 C20 H20 120.6 . . ?
C20 C19 H19 118.5 . . ?
N5 C19 C20 123.0(2) . . ?
N5 C19 H19 118.5 . . ?
C22 N5 Fe1 110.75(17) . . ?
C19 N5 Fe1 130.80(17) . . ?
C19 N5 C22 117.9(2) . . ?
C21 C24 H24 120.2 . . ?
C22 C24 C21 119.7(3) . . ?
C22 C24 H24 120.2 . . ?

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
C6 H6 O4 0.95 2.60 3.146(4) 117.0 .
C3 H3A O2 0.99 2.58 3.550(3) 167.5 2_756
C3 H3B O3 0.99 2.57 3.534(3) 165.7 2_656
C12 H12A O3 0.99 2.55 3.508(3) 161.7 2_656
C14 H14 O2 0.95 2.61 3.146(3) 116.3 .
C17 H17A O6 0.99 2.48 3.449(3) 164.5 2_756
C17 H17B O1 0.99 2.49 3.257(3) 133.5 2_756
C19 H19 O3 0.95 2.49 3.412(3) 162.9 2_656

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 N2 C3 C18 -33.2(2) . . . . ?
Fe1 N2 C12 C13 38.7(2) . . . . ?
Fe1 N2 C17 C1 26.3(2) . . . . ?
Fe1 O2 C23 C22 1.3(3) . . . . ?
Fe1 O2 C23 O1 -179.0(2) . . . . ?
N2 Fe1 O2 C23 175.2(4) . . . . ?
N2 Fe1 N4 C1 -1.86(16) . . . . ?
N2 Fe1 N4 C14 -168.78(19) . . . . ?
N2 Fe1 N3 C11 -165.8(2) . . . . ?
N2 Fe1 N3 C13 18.24(17) . . . . ?
N2 Fe1 N1 C7 166.6(2) . . . . ?
N2 Fe1 N1 C18 -7.62(17) . . . . ?
N2 Fe1 N5 C22 -173.75(16) . . . . ?
N2 Fe1 N5 C19 -2.9(2) . . . . ?
N2 C3 C18 C4 -155.3(2) . . . . ?
N2 C3 C18 N1 29.1(3) . . . . ?
O2 Fe1 N2 C3 108.9(5) . . . . ?
O2 Fe1 N2 C12 -130.4(4) . . . . ?
O2 Fe1 N2 C17 -13.1(5) . . . . ?
O2 Fe1 N4 C1 178.18(16) . . . . ?
O2 Fe1 N4 C14 11.26(19) . . . . ?
O2 Fe1 N3 C11 4.8(2) . . . . ?
O2 Fe1 N3 C13 -171.17(17) . . . . ?
O2 Fe1 N1 C7 -4.0(2) . . . . ?
O2 Fe1 N1 C18 -178.25(17) . . . . ?
O2 Fe1 N5 C22 6.12(16) . . . . ?
O2 Fe1 N5 C19 176.9(2) . . . . ?
C6 C7 N1 Fe1 -175.59(18) . . . . ?
C6 C7 N1 C18 -1.4(4) . . . . ?
C9 C11 N3 Fe1 -175.9(2) . . . . ?
C9 C11 N3 C13 0.0(4) . . . . ?
C4 C18 N1 Fe1 175.5(2) . . . . ?
C4 C18 N1 C7 0.8(4) . . . . ?
C8 C13 C12 N2 156.3(2) . . . . ?
C8 C13 N3 Fe1 176.2(2) . . . . ?
C8 C13 N3 C11 -0.1(4) . . . . ?
C7 C6 C5 C4 0.4(4) . . . . ?
C3 N2 C12 C13 157.8(2) . . . . ?
C3 N2 C17 C1 -93.0(2) . . . . ?
C3 C18 N1 Fe1 -9.0(3) . . . . ?
C3 C18 N1 C7 176.4(2) . . . . ?
C2 C1 C17 N2 154.0(2) . . . . ?
C2 C1 N4 Fe1 -167.36(18) . . . . ?
C2 C1 N4 C14 0.7(3) . . . . ?
C11 C9 C10 C8 -2.2(5) . . . . ?
C5 C6 C7 N1 0.8(4) . . . . ?
C5 C4 C18 C3 -175.0(2) . . . . ?
C5 C4 C18 N1 0.3(4) . . . . ?
C1 C2 C16 C15 -1.2(4) . . . . ?
C18 C4 C5 C6 -0.9(4) . . . . ?
C10 C9 C11 N3 1.1(4) . . . . ?
C10 C8 C13 C12 176.9(3) . . . . ?
C10 C8 C13 N3 -1.1(4) . . . . ?
C13 C8 C10 C9 2.2(5) . . . . ?
C12 N2 C3 C18 -152.1(2) . . . . ?
C12 N2 C17 C1 143.1(2) . . . . ?
C12 C13 N3 Fe1 -1.9(3) . . . . ?
C12 C13 N3 C11 -178.1(2) . . . . ?
C14 C15 C16 C2 1.3(4) . . . . ?
C17 N2 C3 C18 85.2(2) . . . . ?
C17 N2 C12 C13 -77.3(2) . . . . ?
C17 C1 N4 Fe1 17.6(3) . . . . ?
C17 C1 N4 C14 -174.4(2) . . . . ?
C15 C14 N4 Fe1 166.01(19) . . . . ?
C15 C14 N4 C1 -0.5(3) . . . . ?
C16 C2 C1 C17 175.1(2) . . . . ?
C16 C2 C1 N4 0.2(4) . . . . ?
N4 Fe1 N2 C3 108.66(16) . . . . ?
N4 Fe1 N2 C12 -130.65(16) . . . . ?
N4 Fe1 N2 C17 -13.39(13) . . . . ?
N4 Fe1 O2 C23 175.48(18) . . . . ?
N4 Fe1 N3 C11 -88.5(2) . . . . ?
N4 Fe1 N3 C13 95.47(19) . . . . ?
N4 Fe1 N1 C7 86.0(2) . . . . ?
N4 Fe1 N1 C18 -88.24(18) . . . . ?
N4 Fe1 N5 C22 3.6(5) . . . . ?
N4 Fe1 N5 C19 174.4(3) . . . . ?
N4 C1 C17 N2 -30.9(3) . . . . ?
N4 C14 C15 C16 -0.4(4) . . . . ?
N3 Fe1 N2 C3 -151.06(17) . . . . ?
N3 Fe1 N2 C12 -30.37(15) . . . . ?
N3 Fe1 N2 C17 86.89(15) . . . . ?
N3 Fe1 O2 C23 77.77(19) . . . . ?
N3 Fe1 N4 C1 -75.07(17) . . . . ?
N3 Fe1 N4 C14 118.01(19) . . . . ?
N3 Fe1 N1 C7 -179.42(17) . . . . ?
N3 Fe1 N1 C18 6.3(3) . . . . ?
N3 Fe1 N5 C22 -101.74(17) . . . . ?
N3 Fe1 N5 C19 69.1(2) . . . . ?
N3 C13 C12 N2 -25.7(3) . . . . ?
N1 Fe1 N2 C3 21.99(15) . . . . ?
N1 Fe1 N2 C12 142.68(17) . . . . ?
N1 Fe1 N2 C17 -100.06(15) . . . . ?
N1 Fe1 O2 C23 -99.93(18) . . . . ?
N1 Fe1 N4 C1 75.78(16) . . . . ?
N1 Fe1 N4 C14 -91.14(19) . . . . ?
N1 Fe1 N3 C11 -179.82(18) . . . . ?
N1 Fe1 N3 C13 4.2(3) . . . . ?
N1 Fe1 N5 C22 107.17(17) . . . . ?
N1 Fe1 N5 C19 -82.0(2) . . . . ?
C21 C20 C19 N5 -1.1(4) . . . . ?
C23 C22 N5 Fe1 -7.3(3) . . . . ?
C23 C22 N5 C19 -179.5(2) . . . . ?
C23 C22 C24 C21 178.8(2) . . . . ?
C20 C21 C24 C22 0.0(4) . . . . ?
C20 C19 N5 Fe1 -169.09(17) . . . . ?
C20 C19 N5 C22 1.2(4) . . . . ?
N5 Fe1 N2 C3 -71.86(17) . . . . ?
N5 Fe1 N2 C12 48.84(17) . . . . ?
N5 Fe1 N2 C17 166.10(14) . . . . ?
N5 Fe1 O2 C23 -4.04(18) . . . . ?
N5 Fe1 N4 C1 -179.3(3) . . . . ?
N5 Fe1 N4 C14 13.7(5) . . . . ?
N5 Fe1 N3 C11 80.8(2) . . . . ?
N5 Fe1 N3 C13 -95.15(18) . . . . ?
N5 Fe1 N1 C7 -83.30(19) . . . . ?
N5 Fe1 N1 C18 102.43(18) . . . . ?
N5 C22 C23 O2 4.5(3) . . . . ?
N5 C22 C23 O1 -175.2(2) . . . . ?
N5 C22 C24 C21 0.1(4) . . . . ?
C24 C21 C20 C19 0.5(4) . . . . ?
C24 C22 C23 O2 -174.3(2) . . . . ?
C24 C22 C23 O1 6.1(4) . . . . ?
C24 C22 N5 Fe1 171.46(19) . . . . ?
C24 C22 N5 C19 -0.7(4) . . . . ?

