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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# 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. 
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data_umd1203a_a
_database_code_depnum_ccdc_archive 'CCDC 1839625'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H48 Cl2 Fe N8'
_chemical_formula_weight         1079.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.9726(2)
_cell_length_b                   17.3320(4)
_cell_length_c                   17.2173(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.2500(10)
_cell_angle_gamma                90
_cell_volume                     2676.88(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      68.27

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.573
_shelx_estimated_absorpt_T_min   0.521
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.331
_exptl_absorpt_correction_T_max  0.467
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38418
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.619
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_full        68.250
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4910
_reflns_number_gt                4443
_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. 

Disorder (0.460/0.540) found for carbon atoms C22-C27 and treated using 
fixed hexagonal ridge ring constraint and rigu command.

RIGU command used for carbon atoms C22, C23, C24, C25, C26, C27
and C22', C23' C24' c25' c26' and C27'

;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0668P)²+0.6839P] 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
_refine_ls_extinction_coef       0.0025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4910
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001

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 0.0000 1.0000 0.5000 0.03342(13) Uani 1 2 d S . P . .
Cl1 Cl 0.25261(5) 1.03042(3) 0.53619(3) 0.04702(15) Uani 1 1 d . . . . .
N1 N 0.06241(18) 0.87604(8) 0.47851(9) 0.0400(3) Uani 1 1 d . . . . .
N2 N 0.26098(17) 0.62830(8) 0.37591(8) 0.0370(3) Uani 1 1 d . . . . .
N3 N 0.44654(18) 0.52149(9) 0.12799(9) 0.0384(3) Uani 1 1 d . . . . .
N4 N 0.2412(2) 0.28668(10) 0.73087(10) 0.0510(4) Uani 1 1 d . . . . .
C1 C -0.0190(2) 0.81676(13) 0.50154(13) 0.0559(6) Uani 1 1 d . . . . .
H1A H -0.1095 0.8271 0.5246 0.067 Uiso 1 1 calc R U . . .
C2 C 0.0229(3) 0.74082(12) 0.49325(14) 0.0558(6) Uani 1 1 d . . . . .
H2B H -0.0371 0.7015 0.5119 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1540(2) 0.72362(10) 0.45724(10) 0.0381(4) Uani 1 1 d . . . . .
C4 C 0.2355(2) 0.78493(11) 0.42923(13) 0.0509(5) Uani 1 1 d . . . . .
H4A H 0.3220 0.7761 0.4019 0.061 Uiso 1 1 calc R U . . .
C5 C 0.1875(2) 0.85929(11) 0.44215(13) 0.0503(5) Uani 1 1 d . . . . .
H5A H 0.2457 0.8998 0.4245 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2063(2) 0.64319(10) 0.44615(10) 0.0367(4) Uani 1 1 d . . . . .
C7 C 0.2005(2) 0.58821(10) 0.50472(10) 0.0395(4) Uani 1 1 d . . . . .
H7A H 0.1620 0.6011 0.5527 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2525(2) 0.51357(10) 0.49141(10) 0.0364(4) Uani 1 1 d . . . . .
C9 C 0.3093(2) 0.49865(9) 0.41811(11) 0.0369(4) Uani 1 1 d . . . . .
H9A H 0.3458 0.4499 0.4065 0.044 Uiso 1 1 calc R U . . .
C10 C 0.31127(19) 0.55655(10) 0.36257(10) 0.0352(4) Uani 1 1 d . . . . .
C11 C 0.3626(2) 0.54352(9) 0.28225(10) 0.0358(4) Uani 1 1 d . . . . .
C12 C 0.4836(2) 0.49778(11) 0.26401(12) 0.0448(5) Uani 1 1 d . . . . .
H12A H 0.5386 0.4731 0.3031 0.054 Uiso 1 1 calc R U . . .
C13 C 0.5214(2) 0.48930(11) 0.18701(12) 0.0460(5) Uani 1 1 d . . . . .
H13A H 0.6042 0.4593 0.1759 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3287(2) 0.56493(12) 0.14641(11) 0.0464(5) Uani 1 1 d . . . . .
H14A H 0.2725 0.5870 0.1062 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2866(2) 0.57857(12) 0.22145(11) 0.0461(5) Uani 1 1 d . . . . .
H15A H 0.2071 0.6113 0.2312 0.055 Uiso 1 1 calc R U . . .
C16 C 0.2470(2) 0.45370(10) 0.55219(10) 0.0375(4) Uani 1 1 d . . . . .
C17 C 0.1348(2) 0.45231(12) 0.60703(11) 0.0458(4) Uani 1 1 d . . . . .
H17A H 0.0605 0.4897 0.6046 0.055 Uiso 1 1 calc R U . . .
C18 C 0.1309(2) 0.39727(12) 0.66465(12) 0.0473(5) Uani 1 1 d . . . . .
H18A H 0.0530 0.3975 0.6994 0.057 Uiso 1 1 calc R U . . .
C19 C 0.2423(2) 0.34115(11) 0.67169(11) 0.0409(4) Uani 1 1 d . . . . .
C20 C 0.3543(2) 0.34159(11) 0.61663(11) 0.0435(4) Uani 1 1 d . . . . .
H20A H 0.4294 0.3047 0.6194 0.052 Uiso 1 1 calc R U . . .
C21 C 0.3551(2) 0.39597(11) 0.55813(11) 0.0403(4) Uani 1 1 d . . . . .
H21A H 0.4299 0.3941 0.5216 0.048 Uiso 1 1 calc R U . . .
C22 C 0.3559(8) 0.2269(4) 0.7345(5) 0.041(4) Uani 0.46(3) 1 d G . P A 1
C23 C 0.4774(13) 0.2428(8) 0.7833(9) 0.081(3) Uani 0.46(3) 1 d G . P A 1
H23A H 0.4807 0.2887 0.8114 0.097 Uiso 0.46(3) 1 calc R U P A 1
C24 C 0.5941(16) 0.1903(12) 0.7902(10) 0.113(5) Uani 0.46(3) 1 d G . P A 1
H24A H 0.6754 0.2010 0.8228 0.136 Uiso 0.46(3) 1 calc R U P A 1
C25 C 0.5891(17) 0.1218(9) 0.7482(6) 0.114(5) Uani 0.46(3) 1 d G . P A 1
H25A H 0.6672 0.0867 0.7528 0.137 Uiso 0.46(3) 1 calc R U P A 1
C26 C 0.4676(16) 0.1058(4) 0.6994(8) 0.085(4) Uani 0.46(3) 1 d G . P A 1
H26A H 0.4643 0.0600 0.6713 0.102 Uiso 0.46(3) 1 calc R U P A 1
C27 C 0.3510(11) 0.1584(6) 0.6925(8) 0.050(2) Uani 0.46(3) 1 d G . P A 1
H27A H 0.2697 0.1477 0.6599 0.060 Uiso 0.46(3) 1 calc R U P A 1
C22' C 0.3500(7) 0.2296(4) 0.7378(4) 0.056(4) Uani 0.54(3) 1 d G . P A 2
C23' C 0.4419(11) 0.2238(4) 0.8036(5) 0.068(2) Uani 0.54(3) 1 d G . P A 2
H23B H 0.4363 0.2606 0.8427 0.081 Uiso 0.54(3) 1 calc R U P A 2
C24' C 0.5419(13) 0.1629(6) 0.8110(4) 0.080(3) Uani 0.54(3) 1 d G . P A 2
H24B H 0.6034 0.1590 0.8551 0.096 Uiso 0.54(3) 1 calc R U P A 2
C25' C 0.5502(11) 0.1078(4) 0.7526(4) 0.071(2) Uani 0.54(3) 1 d G . P A 2
H25B H 0.6171 0.0670 0.7576 0.085 Uiso 0.54(3) 1 calc R U P A 2
C26' C 0.4583(10) 0.1136(5) 0.6868(4) 0.062(2) Uani 0.54(3) 1 d G . P A 2
H26B H 0.4638 0.0767 0.6477 0.074 Uiso 0.54(3) 1 calc R U P A 2
C27' C 0.3583(10) 0.1745(6) 0.6794(4) 0.0460(18) Uani 0.54(3) 1 d G . P A 2
H27B H 0.2968 0.1784 0.6354 0.055 Uiso 0.54(3) 1 calc R U P A 2
C28 C 0.1418(2) 0.29156(12) 0.79472(12) 0.0499(5) Uani 1 1 d . . . . .
C29 C 0.0525(4) 0.23029(16) 0.81191(19) 0.0843(9) Uani 1 1 d . . . . .
H29A H 0.0521 0.1866 0.7806 0.101 Uiso 1 1 calc R U . . .
C30 C -0.0390(4) 0.2336(2) 0.8774(2) 0.0983(11) Uani 1 1 d . . . . .
H30A H -0.1000 0.1920 0.8891 0.118 Uiso 1 1 calc R U . . .
C33 C 0.1401(3) 0.35527(15) 0.84344(13) 0.0602(6) Uani 1 1 d . . . . .
H33A H 0.2023 0.3969 0.8337 0.072 Uiso 1 1 calc R U . . .
C31 C -0.0389(3) 0.2966(2) 0.92324(17) 0.0789(8) Uani 1 1 d . . . . .
H31A H -0.0985 0.2979 0.9667 0.095 Uiso 1 1 calc R U . . .
C32 C 0.0473(3) 0.35755(18) 0.90616(15) 0.0728(7) Uani 1 1 d . . . . .
H32A H 0.0443 0.4016 0.9369 0.087 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 N1 2.2528(14) 3_576 ?
Fe1 N1 2.2528(14) . ?
Fe1 N3 2.2960(14) 4_576 ?
Fe1 N3 2.2960(14) 2 ?
Fe1 Cl1 2.3963(5) 3_576 ?
Fe1 Cl1 2.3963(5) . ?
N1 C1 1.326(3) . ?
N1 C5 1.329(2) . ?
N2 C6 1.340(2) . ?
N2 C10 1.344(2) . ?
N3 C13 1.329(3) . ?
N3 C14 1.342(2) . ?
N3 Fe1 2.2959(14) 2_545 ?
N4 C19 1.389(2) . ?
N4 C22' 1.394(5) . ?
N4 C28 1.433(3) . ?
N4 C22 1.461(6) . ?
C1 C2 1.377(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.375(3) . ?
C2 H2B 0.9300 . ?
C3 C4 1.382(3) . ?
C3 C6 1.484(2) . ?
C4 C5 1.378(3) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.389(2) . ?
C7 C8 1.396(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.395(3) . ?
C8 C16 1.475(2) . ?
C9 C10 1.387(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.484(2) . ?
C11 C15 1.378(3) . ?
C11 C12 1.386(3) . ?
C12 C13 1.384(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(3) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.395(3) . ?
C16 C21 1.396(2) . ?
C17 C18 1.377(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.398(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.396(3) . ?
C20 C21 1.380(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 C23 1.3900 . ?
C22 C27 1.3900 . ?
C23 C24 1.3900 . ?
C23 H23A 0.9300 . ?
C24 C25 1.3900 . ?
C24 H24A 0.9300 . ?
C25 C26 1.3900 . ?
C25 H25A 0.9300 . ?
C26 C27 1.3900 . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?
C22' C23' 1.3900 . ?
C22' C27' 1.3900 . ?
C23' C24' 1.3900 . ?
C23' H23B 0.9300 . ?
C24' C25' 1.3900 . ?
C24' H24B 0.9300 . ?
C25' C26' 1.3900 . ?
C25' H25B 0.9300 . ?
C26' C27' 1.3900 . ?
C26' H26B 0.9300 . ?
C27' H27B 0.9300 . ?
C28 C29 1.366(3) . ?
C28 C33 1.387(3) . ?
C29 C30 1.411(4) . ?
C29 H29A 0.9300 . ?
C30 C31 1.346(5) . ?
C30 H30A 0.9300 . ?
C33 C32 1.378(3) . ?
C33 H33A 0.9300 . ?
C31 C32 1.346(4) . ?
C31 H31A 0.9300 . ?
C32 H32A 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
N1 Fe1 N1 180.0 3_576 . ?
N1 Fe1 N3 86.51(5) 3_576 4_576 ?
N1 Fe1 N3 93.49(5) . 4_576 ?
N1 Fe1 N3 93.49(5) 3_576 2 ?
N1 Fe1 N3 86.51(5) . 2 ?
N3 Fe1 N3 180.0 4_576 2 ?
N1 Fe1 Cl1 90.89(4) 3_576 3_576 ?
N1 Fe1 Cl1 89.11(4) . 3_576 ?
N3 Fe1 Cl1 89.87(4) 4_576 3_576 ?
N3 Fe1 Cl1 90.13(4) 2 3_576 ?
N1 Fe1 Cl1 89.11(4) 3_576 . ?
N1 Fe1 Cl1 90.89(4) . . ?
N3 Fe1 Cl1 90.13(4) 4_576 . ?
N3 Fe1 Cl1 89.87(4) 2 . ?
Cl1 Fe1 Cl1 180.0 3_576 . ?
C1 N1 C5 116.60(16) . . ?
C1 N1 Fe1 123.32(12) . . ?
C5 N1 Fe1 120.07(13) . . ?
C6 N2 C10 117.59(15) . . ?
C13 N3 C14 116.28(16) . . ?
C13 N3 Fe1 123.59(12) . 2_545 ?
C14 N3 Fe1 120.01(12) . 2_545 ?
C19 N4 C22' 122.0(3) . . ?
C19 N4 C28 122.48(17) . . ?
C22' N4 C28 115.0(3) . . ?
C19 N4 C22 119.8(4) . . ?
C28 N4 C22 117.3(4) . . ?
N1 C1 C2 123.81(19) . . ?
N1 C1 H1A 118.1 . . ?
C2 C1 H1A 118.1 . . ?
C3 C2 C1 119.48(19) . . ?
C3 C2 H2B 120.3 . . ?
C1 C2 H2B 120.3 . . ?
C2 C3 C4 117.05(17) . . ?
C2 C3 C6 122.52(17) . . ?
C4 C3 C6 120.40(16) . . ?
C5 C4 C3 119.56(18) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
N1 C5 C4 123.36(19) . . ?
N1 C5 H5A 118.3 . . ?
C4 C5 H5A 118.3 . . ?
N2 C6 C7 122.91(16) . . ?
N2 C6 C3 114.83(15) . . ?
C7 C6 C3 122.26(15) . . ?
C6 C7 C8 119.90(16) . . ?
C6 C7 H7A 120.0 . . ?
C8 C7 H7A 120.0 . . ?
C9 C8 C7 116.76(16) . . ?
C9 C8 C16 121.99(16) . . ?
C7 C8 C16 121.25(16) . . ?
C10 C9 C8 120.01(15) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
N2 C10 C9 122.84(15) . . ?
N2 C10 C11 114.33(15) . . ?
C9 C10 C11 122.78(15) . . ?
C15 C11 C12 117.20(16) . . ?
C15 C11 C10 118.84(16) . . ?
C12 C11 C10 123.96(17) . . ?
C13 C12 C11 119.20(18) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
N3 C13 C12 123.89(18) . . ?
N3 C13 H13A 118.1 . . ?
C12 C13 H13A 118.1 . . ?
N3 C14 C15 123.57(18) . . ?
N3 C14 H14A 118.2 . . ?
C15 C14 H14A 118.2 . . ?
C14 C15 C11 119.79(17) . . ?
C14 C15 H15A 120.1 . . ?
C11 C15 H15A 120.1 . . ?
C17 C16 C21 116.65(16) . . ?
C17 C16 C8 121.89(16) . . ?
C21 C16 C8 121.46(16) . . ?
C18 C17 C16 121.98(17) . . ?
C18 C17 H17A 119.0 . . ?
C16 C17 H17A 119.0 . . ?
C17 C18 C19 121.01(17) . . ?
C17 C18 H18A 119.5 . . ?
C19 C18 H18A 119.5 . . ?
N4 C19 C20 121.22(17) . . ?
N4 C19 C18 121.34(17) . . ?
C20 C19 C18 117.44(16) . . ?
C21 C20 C19 121.01(17) . . ?
C21 C20 H20A 119.5 . . ?
C19 C20 H20A 119.5 . . ?
C20 C21 C16 121.87(17) . . ?
C20 C21 H21A 119.1 . . ?
C16 C21 H21A 119.1 . . ?
C23 C22 C27 120.0 . . ?
C23 C22 N4 115.3(6) . . ?
C27 C22 N4 124.7(6) . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C26 C25 H25A 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26A 120.0 . . ?
C25 C26 H26A 120.0 . . ?
C26 C27 C22 120.0 . . ?
C26 C27 H27A 120.0 . . ?
C22 C27 H27A 120.0 . . ?
C23' C22' C27' 120.0 . . ?
C23' C22' N4 121.5(5) . . ?
C27' C22' N4 118.3(5) . . ?
C22' C23' C24' 120.0 . . ?
C22' C23' H23B 120.0 . . ?
C24' C23' H23B 120.0 . . ?
C23' C24' C25' 120.0 . . ?
C23' C24' H24B 120.0 . . ?
C25' C24' H24B 120.0 . . ?
C26' C25' C24' 120.0 . . ?
C26' C25' H25B 120.0 . . ?
C24' C25' H25B 120.0 . . ?
C25' C26' C27' 120.0 . . ?
C25' C26' H26B 120.0 . . ?
C27' C26' H26B 120.0 . . ?
C26' C27' C22' 120.0 . . ?
C26' C27' H27B 120.0 . . ?
C22' C27' H27B 120.0 . . ?
C29 C28 C33 118.3(2) . . ?
C29 C28 N4 119.9(2) . . ?
C33 C28 N4 121.73(19) . . ?
C28 C29 C30 119.7(3) . . ?
C28 C29 H29A 120.1 . . ?
C30 C29 H29A 120.1 . . ?
C31 C30 C29 120.5(3) . . ?
C31 C30 H30A 119.7 . . ?
C29 C30 H30A 119.7 . . ?
C32 C33 C28 120.7(2) . . ?
C32 C33 H33A 119.6 . . ?
C28 C33 H33A 119.6 . . ?
C30 C31 C32 120.1(3) . . ?
C30 C31 H31A 119.9 . . ?
C32 C31 H31A 119.9 . . ?
C31 C32 C33 120.6(3) . . ?
C31 C32 H32A 119.7 . . ?
C33 C32 H32A 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 3.3(3) . . . . ?
Fe1 N1 C1 C2 -175.59(19) . . . . ?
N1 C1 C2 C3 -1.9(4) . . . . ?
C1 C2 C3 C4 -1.7(3) . . . . ?
C1 C2 C3 C6 -179.9(2) . . . . ?
C2 C3 C4 C5 3.6(3) . . . . ?
C6 C3 C4 C5 -178.0(2) . . . . ?
C1 N1 C5 C4 -1.2(3) . . . . ?
Fe1 N1 C5 C4 177.78(18) . . . . ?
C3 C4 C5 N1 -2.3(4) . . . . ?
C10 N2 C6 C7 0.3(3) . . . . ?
C10 N2 C6 C3 179.45(16) . . . . ?
C2 C3 C6 N2 136.7(2) . . . . ?
C4 C3 C6 N2 -41.5(3) . . . . ?
C2 C3 C6 C7 -44.1(3) . . . . ?
C4 C3 C6 C7 137.6(2) . . . . ?
N2 C6 C7 C8 -0.3(3) . . . . ?
C3 C6 C7 C8 -179.36(17) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C8 C16 -179.58(17) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C16 C8 C9 C10 179.52(17) . . . . ?
C6 N2 C10 C9 -0.4(3) . . . . ?
C6 N2 C10 C11 176.94(16) . . . . ?
C8 C9 C10 N2 0.4(3) . . . . ?
C8 C9 C10 C11 -176.69(17) . . . . ?
N2 C10 C11 C15 -36.8(2) . . . . ?
C9 C10 C11 C15 140.5(2) . . . . ?
N2 C10 C11 C12 143.22(18) . . . . ?
C9 C10 C11 C12 -39.5(3) . . . . ?
C15 C11 C12 C13 -0.3(3) . . . . ?
C10 C11 C12 C13 179.71(18) . . . . ?
C14 N3 C13 C12 0.6(3) . . . . ?
Fe1 N3 C13 C12 -175.41(16) 2_545 . . . ?
C11 C12 C13 N3 -1.3(3) . . . . ?
C13 N3 C14 C15 1.8(3) . . . . ?
Fe1 N3 C14 C15 177.95(17) 2_545 . . . ?
N3 C14 C15 C11 -3.4(3) . . . . ?
C12 C11 C15 C14 2.5(3) . . . . ?
C10 C11 C15 C14 -177.51(18) . . . . ?
C9 C8 C16 C17 -148.2(2) . . . . ?
C7 C8 C16 C17 31.7(3) . . . . ?
C9 C8 C16 C21 32.5(3) . . . . ?
C7 C8 C16 C21 -147.62(19) . . . . ?
C21 C16 C17 C18 0.5(3) . . . . ?
C8 C16 C17 C18 -178.84(19) . . . . ?
C16 C17 C18 C19 1.6(3) . . . . ?
C22' N4 C19 C20 -0.7(5) . . . . ?
C28 N4 C19 C20 170.33(19) . . . . ?
C22 N4 C19 C20 -2.2(5) . . . . ?
C22' N4 C19 C18 178.9(4) . . . . ?
C28 N4 C19 C18 -10.1(3) . . . . ?
C22 N4 C19 C18 177.4(4) . . . . ?
C17 C18 C19 N4 178.3(2) . . . . ?
C17 C18 C19 C20 -2.1(3) . . . . ?
N4 C19 C20 C21 -179.78(19) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C20 C21 C16 1.4(3) . . . . ?
C17 C16 C21 C20 -2.0(3) . . . . ?
C8 C16 C21 C20 177.36(18) . . . . ?
C19 N4 C22 C23 95.7(9) . . . . ?
C28 N4 C22 C23 -77.2(9) . . . . ?
C19 N4 C22 C27 -83.3(9) . . . . ?
C28 N4 C22 C27 103.8(8) . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
N4 C22 C23 C24 -179.0(6) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C22 0.0 . . . . ?
C23 C22 C27 C26 0.0 . . . . ?
N4 C22 C27 C26 178.9(7) . . . . ?
C19 N4 C22' C23' 119.5(7) . . . . ?
C28 N4 C22' C23' -52.1(8) . . . . ?
C19 N4 C22' C27' -65.0(6) . . . . ?
C28 N4 C22' C27' 123.4(5) . . . . ?
C27' C22' C23' C24' 0.0 . . . . ?
N4 C22' C23' C24' 175.4(6) . . . . ?
C22' C23' C24' C25' 0.0 . . . . ?
C23' C24' C25' C26' 0.0 . . . . ?
C24' C25' C26' C27' 0.0 . . . . ?
C25' C26' C27' C22' 0.0 . . . . ?
C23' C22' C27' C26' 0.0 . . . . ?
N4 C22' C27' C26' -175.5(6) . . . . ?
C19 N4 C28 C29 126.3(3) . . . . ?
C22' N4 C28 C29 -62.1(5) . . . . ?
C22 N4 C28 C29 -61.0(5) . . . . ?
C19 N4 C28 C33 -58.1(3) . . . . ?
C22' N4 C28 C33 113.5(4) . . . . ?
C22 N4 C28 C33 114.6(4) . . . . ?
C33 C28 C29 C30 0.7(4) . . . . ?
N4 C28 C29 C30 176.4(3) . . . . ?
C28 C29 C30 C31 -0.2(5) . . . . ?
C29 C28 C33 C32 -2.0(4) . . . . ?
N4 C28 C33 C32 -177.7(2) . . . . ?
C29 C30 C31 C32 1.0(5) . . . . ?
C30 C31 C32 C33 -2.3(5) . . . . ?
C28 C33 C32 C31 2.8(4) . . . . ?

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
C1 H1A Cl1 0.93 2.96 3.431(2) 112.6 3_576
C5 H5A Cl1 0.93 2.97 3.423(2) 111.6 .
C13 H13A Cl1 0.93 2.78 3.376(2) 122.8 4_675
C14 H14A Cl1 0.93 2.65 3.267(2) 124.8 2_545
C27 H27A Cl1 0.93 2.94 3.583(9) 127.0 1_545

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.050

_shelxl_version_number           2014/6

