# 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_pnm124_105K
_database_code_depnum_ccdc_archive 'CCDC 1579737'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 Br2 Cl Fe N4 O6'
_chemical_formula_weight         695.60

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.7817(9)
_cell_length_b                   23.4602(19)
_cell_length_c                   11.8961(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.885(2)
_cell_angle_gamma                90
_cell_volume                     2650.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    6110
_cell_measurement_theta_min      2.4749
_cell_measurement_theta_max      27.4321

_exptl_crystal_description       block
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             1396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .10
_exptl_crystal_size_mid          .05
_exptl_crystal_size_min          .04
_exptl_absorpt_coefficient_mu    3.730
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756586
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      105(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 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29736
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.736
_diffrn_reflns_theta_max         27.582
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6010
_reflns_number_gt                4688
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0342P)²+1.4636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6010
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.20253(3) 0.37347(2) 0.71938(3) 0.01795(9) Uani 1 1 d . . . . .
C1 C -0.1567(3) 0.35803(12) 0.4181(2) 0.0379(7) Uani 1 1 d . . . . .
H1A H -0.1771 0.3174 0.4240 0.057 Uiso 1 1 calc R U . . .
H1B H -0.1091 0.3639 0.3554 0.057 Uiso 1 1 calc R U . . .
H1C H -0.2450 0.3797 0.4018 0.057 Uiso 1 1 calc R U . . .
C2 C -0.0622(3) 0.37837(11) 0.5315(2) 0.0289(6) Uani 1 1 d . . . . .
H2A H -0.0529 0.4203 0.5283 0.035 Uiso 1 1 calc R U . . .
H2B H -0.1081 0.3694 0.5950 0.035 Uiso 1 1 calc R U . . .
N1 N 0.0809(2) 0.35275(9) 0.55926(18) 0.0229(4) Uani 1 1 d . . . . .
H1 H 0.123(3) 0.3609(12) 0.508(2) 0.027 Uiso 1 1 d . U . . .
C3 C 0.0759(3) 0.28961(11) 0.5545(2) 0.0264(5) Uani 1 1 d . . . . .
H3A H 0.0424 0.2766 0.4733 0.032 Uiso 1 1 calc R U . . .
H3B H 0.0104 0.2750 0.5996 0.032 Uiso 1 1 calc R U . . .
C4 C 0.2225(3) 0.26777(11) 0.6049(2) 0.0255(5) Uani 1 1 d . . . . .
H4A H 0.2208 0.2260 0.6170 0.031 Uiso 1 1 calc R U . . .
H4B H 0.2841 0.2760 0.5519 0.031 Uiso 1 1 calc R U . . .
N2 N 0.27463(19) 0.29708(8) 0.71570(16) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.3617(2) 0.27132(10) 0.7974(2) 0.0203(5) Uani 1 1 d . . . . .
H5 H 0.3883 0.2335 0.7836 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4217(2) 0.29604(10) 0.90899(19) 0.0193(5) Uani 1 1 d . . . . .
C7 C 0.3875(2) 0.35178(10) 0.93916(19) 0.0197(5) Uani 1 1 d . . . . .
O1 O 0.31520(17) 0.38908(7) 0.86658(13) 0.0210(4) Uani 1 1 d . . . . .
C8 C 0.4387(2) 0.36884(10) 1.0560(2) 0.0225(5) Uani 1 1 d . . . . .
H8 H 0.4083 0.4041 1.0810 0.027 Uiso 1 1 calc R U . . .
C9 C 0.5313(3) 0.33552(10) 1.1339(2) 0.0243(5) Uani 1 1 d . . . . .
H9 H 0.5656 0.3480 1.2115 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5747(2) 0.28334(10) 1.0985(2) 0.0239(5) Uani 1 1 d . . . . .
Br1 Br 0.71411(3) 0.24016(2) 1.20306(2) 0.03391(8) Uani 1 1 d . . . . .
C11 C 0.5185(2) 0.26299(10) 0.9893(2) 0.0223(5) Uani 1 1 d . . . . .
H11 H 0.5451 0.2264 0.9678 0.027 Uiso 1 1 calc R U . . .
C21 C 0.6010(3) 0.41441(12) 0.6237(3) 0.0355(6) Uani 1 1 d . . . . .
H21A H 0.6158 0.4536 0.6526 0.053 Uiso 1 1 calc R U . . .
H21B H 0.5651 0.4149 0.5394 0.053 Uiso 1 1 calc R U . . .
H21C H 0.6904 0.3936 0.6436 0.053 Uiso 1 1 calc R U . . .
C22 C 0.4949(2) 0.38504(11) 0.6788(2) 0.0270(6) Uani 1 1 d . . . . .
H22A H 0.4885 0.3444 0.6556 0.032 Uiso 1 1 calc R U . . .
H22B H 0.5300 0.3866 0.7640 0.032 Uiso 1 1 calc R U . . .
N3 N 0.3521(2) 0.41024(9) 0.64703(18) 0.0208(4) Uani 1 1 d . . . . .
H3 H 0.329(3) 0.4066(11) 0.577(2) 0.025 Uiso 1 1 d . U . . .
C23 C 0.3542(3) 0.47203(10) 0.6752(2) 0.0273(6) Uani 1 1 d . . . . .
H23A H 0.4032 0.4937 0.6250 0.033 Uiso 1 1 calc R U . . .
H23B H 0.4043 0.4784 0.7570 0.033 Uiso 1 1 calc R U . . .
C24 C 0.2041(3) 0.49128(11) 0.6551(2) 0.0281(6) Uani 1 1 d . . . . .
H24A H 0.1995 0.5304 0.6852 0.034 Uiso 1 1 calc R U . . .
H29B H 0.1582 0.4910 0.5714 0.034 Uiso 1 1 calc R U . . .
N4 N 0.1343(2) 0.45082(8) 0.71731(16) 0.0203(4) Uani 1 1 d . . . . .
C25 C 0.0459(2) 0.46966(10) 0.7718(2) 0.0218(5) Uani 1 1 d . . . . .
H25 H 0.0285 0.5095 0.7698 0.026 Uiso 1 1 calc R U . . .
C26 C -0.0285(2) 0.43468(10) 0.83588(19) 0.0198(5) Uani 1 1 d . . . . .
C27 C -0.0166(2) 0.37443(10) 0.84024(19) 0.0196(5) Uani 1 1 d . . . . .
O2 O 0.05930(16) 0.34414(6) 0.78391(13) 0.0208(3) Uani 1 1 d . . . . .
C28 C -0.0968(2) 0.34540(10) 0.9059(2) 0.0220(5) Uani 1 1 d . . . . .
H28 H -0.0884 0.3051 0.9129 0.026 Uiso 1 1 calc R U . . .
C29 C -0.1862(3) 0.37305(11) 0.9601(2) 0.0251(5) Uani 1 1 d . . . . .
H29 H -0.2398 0.3521 1.0028 0.030 Uiso 1 1 calc R U . . .
C30 C -0.1982(2) 0.43211(10) 0.9519(2) 0.0234(5) Uani 1 1 d . . . . .
Br2 Br -0.32568(3) 0.47212(2) 1.02091(2) 0.03252(8) Uani 1 1 d . . . . .
C31 C -0.1209(2) 0.46244(10) 0.8916(2) 0.0219(5) Uani 1 1 d . . . . .
H31 H -0.1296 0.5028 0.8873 0.026 Uiso 1 1 calc R U . . .
Cl1 Cl 0.25798(7) 0.40260(3) 0.32320(5) 0.03360(16) Uani 1 1 d . . . . .
O3 O 0.1659(3) 0.38780(13) 0.21693(19) 0.0705(8) Uani 1 1 d . . . . .
O4 O 0.1875(2) 0.43972(10) 0.38777(17) 0.0517(6) Uani 1 1 d . . . . .
O5 O 0.3776(3) 0.43070(10) 0.3024(2) 0.0598(7) Uani 1 1 d . . . . .
O6 O 0.3005(3) 0.35333(9) 0.39409(18) 0.0569(6) 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
Fe1 O1 1.8679(16) . ?
Fe1 O2 1.8820(15) . ?
Fe1 N2 1.9302(19) . ?
Fe1 N4 1.931(2) . ?
Fe1 N1 2.047(2) . ?
Fe1 N3 2.057(2) . ?
C1 C2 1.518(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.486(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N1 C3 1.483(3) . ?
N1 H1 0.83(3) . ?
C3 C4 1.505(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N2 1.466(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N2 C5 1.280(3) . ?
C5 C6 1.438(3) . ?
C5 H5 0.9500 . ?
C6 C11 1.406(3) . ?
C6 C7 1.417(3) . ?
C7 O1 1.311(3) . ?
C7 C8 1.418(3) . ?
C8 C9 1.374(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(3) . ?
C10 Br1 1.902(2) . ?
C11 H11 0.9500 . ?
C21 C22 1.519(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N3 1.480(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N3 C23 1.487(3) . ?
N3 H3 0.82(3) . ?
C23 C24 1.499(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N4 1.469(3) . ?
C24 H24A 0.9900 . ?
C24 H29B 0.9900 . ?
N4 C25 1.278(3) . ?
C25 C26 1.432(3) . ?
C25 H25 0.9500 . ?
C26 C31 1.403(3) . ?
C26 C27 1.418(3) . ?
C27 O2 1.321(3) . ?
C27 C28 1.408(3) . ?
C28 C29 1.368(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.392(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.361(3) . ?
C30 Br2 1.898(2) . ?
C31 H31 0.9500 . ?
Cl1 O3 1.409(2) . ?
Cl1 O5 1.415(2) . ?
Cl1 O6 1.432(2) . ?
Cl1 O4 1.442(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O2 91.08(7) . . ?
O1 Fe1 N2 93.82(7) . . ?
O2 Fe1 N2 88.95(7) . . ?
O1 Fe1 N4 87.25(7) . . ?
O2 Fe1 N4 93.43(7) . . ?
N2 Fe1 N4 177.37(8) . . ?
O1 Fe1 N1 177.56(8) . . ?
O2 Fe1 N1 88.26(8) . . ?
N2 Fe1 N1 83.81(8) . . ?
N4 Fe1 N1 95.13(8) . . ?
O1 Fe1 N3 89.49(8) . . ?
O2 Fe1 N3 176.40(8) . . ?
N2 Fe1 N3 94.56(8) . . ?
N4 Fe1 N3 83.05(8) . . ?
N1 Fe1 N3 91.32(8) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 114.3(2) . . ?
N1 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
N1 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C3 N1 C2 112.01(19) . . ?
C3 N1 Fe1 106.23(15) . . ?
C2 N1 Fe1 114.62(15) . . ?
C3 N1 H1 102.6(19) . . ?
C2 N1 H1 110.1(19) . . ?
Fe1 N1 H1 110.6(19) . . ?
N1 C3 C4 107.8(2) . . ?
N1 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
N1 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
N2 C4 C3 106.93(19) . . ?
N2 C4 H4A 110.3 . . ?
C3 C4 H4A 110.3 . . ?
N2 C4 H4B 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
C5 N2 C4 119.09(19) . . ?
C5 N2 Fe1 126.96(16) . . ?
C4 N2 Fe1 113.94(15) . . ?
N2 C5 C6 124.1(2) . . ?
N2 C5 H5 118.0 . . ?
C6 C5 H5 118.0 . . ?
C11 C6 C7 119.9(2) . . ?
C11 C6 C5 117.7(2) . . ?
C7 C6 C5 122.5(2) . . ?
O1 C7 C6 124.9(2) . . ?
O1 C7 C8 117.7(2) . . ?
C6 C7 C8 117.4(2) . . ?
C7 O1 Fe1 126.17(14) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 Br1 119.74(19) . . ?
C9 C10 Br1 119.53(18) . . ?
C10 C11 C6 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C21 114.2(2) . . ?
N3 C22 H22A 108.7 . . ?
C21 C22 H22A 108.7 . . ?
N3 C22 H22B 108.7 . . ?
C21 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C22 N3 C23 111.76(19) . . ?
C22 N3 Fe1 116.63(15) . . ?
C23 N3 Fe1 106.70(14) . . ?
C22 N3 H3 103.5(18) . . ?
C23 N3 H3 108.6(19) . . ?
Fe1 N3 H3 109.4(18) . . ?
N3 C23 C24 107.3(2) . . ?
N3 C23 H23A 110.3 . . ?
C24 C23 H23A 110.3 . . ?
N3 C23 H23B 110.3 . . ?
C24 C23 H23B 110.3 . . ?
H23A C23 H23B 108.5 . . ?
N4 C24 C23 106.32(19) . . ?
N4 C24 H24A 110.5 . . ?
C23 C24 H24A 110.5 . . ?
N4 C24 H29B 110.5 . . ?
C23 C24 H29B 110.5 . . ?
H24A C24 H29B 108.7 . . ?
C25 N4 C24 119.0(2) . . ?
C25 N4 Fe1 126.33(17) . . ?
C24 N4 Fe1 114.36(15) . . ?
N4 C25 C26 124.3(2) . . ?
N4 C25 H25 117.8 . . ?
C26 C25 H25 117.8 . . ?
C31 C26 C27 120.1(2) . . ?
C31 C26 C25 116.9(2) . . ?
C27 C26 C25 122.9(2) . . ?
O2 C27 C28 118.5(2) . . ?
O2 C27 C26 124.7(2) . . ?
C28 C27 C26 116.8(2) . . ?
C27 O2 Fe1 125.07(14) . . ?
C29 C28 C27 122.4(2) . . ?
C29 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
C28 C29 C30 119.5(2) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C31 C30 C29 120.6(2) . . ?
C31 C30 Br2 118.37(18) . . ?
C29 C30 Br2 121.01(18) . . ?
C30 C31 C26 120.6(2) . . ?
C30 C31 H31 119.7 . . ?
C26 C31 H31 119.7 . . ?
O3 Cl1 O5 109.61(15) . . ?
O3 Cl1 O6 111.25(16) . . ?
O5 Cl1 O6 110.07(16) . . ?
O3 Cl1 O4 110.02(16) . . ?
O5 Cl1 O4 109.44(14) . . ?
O6 Cl1 O4 106.39(12) . . ?

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
C1 C2 N1 C3 -52.9(3) . . . . ?
C1 C2 N1 Fe1 -174.02(18) . . . . ?
C2 N1 C3 C4 -169.6(2) . . . . ?
Fe1 N1 C3 C4 -43.8(2) . . . . ?
N1 C3 C4 N2 49.4(3) . . . . ?
C3 C4 N2 C5 149.2(2) . . . . ?
C3 C4 N2 Fe1 -31.7(2) . . . . ?
C4 N2 C5 C6 178.9(2) . . . . ?
Fe1 N2 C5 C6 0.0(3) . . . . ?
N2 C5 C6 C11 -178.6(2) . . . . ?
N2 C5 C6 C7 1.0(4) . . . . ?
C11 C6 C7 O1 169.7(2) . . . . ?
C5 C6 C7 O1 -9.8(4) . . . . ?
C11 C6 C7 C8 -8.5(3) . . . . ?
C5 C6 C7 C8 172.0(2) . . . . ?
C6 C7 O1 Fe1 16.8(3) . . . . ?
C8 C7 O1 Fe1 -165.01(16) . . . . ?
O2 Fe1 O1 C7 76.61(18) . . . . ?
N2 Fe1 O1 C7 -12.40(18) . . . . ?
N4 Fe1 O1 C7 170.00(18) . . . . ?
N3 Fe1 O1 C7 -106.94(18) . . . . ?
O1 C7 C8 C9 -170.9(2) . . . . ?
C6 C7 C8 C9 7.5(3) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C8 C9 C10 C11 -4.7(4) . . . . ?
C8 C9 C10 Br1 175.05(18) . . . . ?
C9 C10 C11 C6 3.6(4) . . . . ?
Br1 C10 C11 C6 -176.15(17) . . . . ?
C7 C6 C11 C10 3.2(3) . . . . ?
C5 C6 C11 C10 -177.3(2) . . . . ?
C21 C22 N3 C23 -56.3(3) . . . . ?
C21 C22 N3 Fe1 -179.38(17) . . . . ?
C22 N3 C23 C24 -172.4(2) . . . . ?
Fe1 N3 C23 C24 -43.8(2) . . . . ?
N3 C23 C24 N4 50.5(3) . . . . ?
C23 C24 N4 C25 140.0(2) . . . . ?
C23 C24 N4 Fe1 -34.2(2) . . . . ?
C24 N4 C25 C26 -179.8(2) . . . . ?
Fe1 N4 C25 C26 -6.4(3) . . . . ?
N4 C25 C26 C31 179.4(2) . . . . ?
N4 C25 C26 C27 -3.4(4) . . . . ?
C31 C26 C27 O2 174.9(2) . . . . ?
C25 C26 C27 O2 -2.3(4) . . . . ?
C31 C26 C27 C28 -2.4(3) . . . . ?
C25 C26 C27 C28 -179.5(2) . . . . ?
C28 C27 O2 Fe1 -165.72(16) . . . . ?
C26 C27 O2 Fe1 17.0(3) . . . . ?
O1 Fe1 O2 C27 67.37(17) . . . . ?
N2 Fe1 O2 C27 161.18(18) . . . . ?
N4 Fe1 O2 C27 -19.94(18) . . . . ?
N1 Fe1 O2 C27 -114.98(18) . . . . ?
O2 C27 C28 C29 -175.1(2) . . . . ?
C26 C27 C28 C29 2.3(3) . . . . ?
C27 C28 C29 C30 -0.9(4) . . . . ?
C28 C29 C30 C31 -0.6(4) . . . . ?
C28 C29 C30 Br2 177.79(18) . . . . ?
C29 C30 C31 C26 0.5(4) . . . . ?
Br2 C30 C31 C26 -177.96(17) . . . . ?
C27 C26 C31 C30 1.1(3) . . . . ?
C25 C26 C31 C30 178.4(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
C2 H2B O2 0.99 2.51 3.060(3) 114.5 .
N1 H1 Cl1 0.83(3) 2.99(3) 3.819(2) 174(2) .
N1 H1 O4 0.83(3) 2.51(3) 3.230(3) 145(2) .
N1 H1 O6 0.83(3) 2.45(3) 3.240(3) 157(3) .
C4 H4B O6 0.99 2.64 3.438(3) 137.4 .
C22 H22A Br1 0.99 2.92 3.607(3) 127.3 4_565
N3 H3 Cl1 0.82(3) 2.93(3) 3.744(2) 175(2) .
N3 H3 O4 0.82(3) 2.46(3) 3.194(3) 149(2) .
N3 H3 O6 0.82(3) 2.46(3) 3.219(3) 154(2) .
C24 H29B O4 0.99 2.57 3.370(3) 137.9 .

_refine_diff_density_max         0.976
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_pnm124_300K
_database_code_depnum_ccdc_archive 'CCDC 1579738'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 Br2 Cl Fe N4 O6'
_chemical_formula_weight         695.60

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.9692(2)
_cell_length_b                   23.6219(6)
_cell_length_c                   12.0380(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.3972(13)
_cell_angle_gamma                90
_cell_volume                     2757.70(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6405
_cell_measurement_theta_min      2.4492
_cell_measurement_theta_max      24.8336

_exptl_crystal_description       block
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_F_000             1396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .05
_exptl_crystal_size_min          .04
_exptl_absorpt_coefficient_mu    3.584
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756586
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(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 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48548
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.724
_diffrn_reflns_theta_max         27.594
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6363
_reflns_number_gt                4405
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0860P)²+5.7136P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6363
_refine_ls_number_parameters     307
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1761
_refine_ls_wR_factor_gt          0.1531
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.036
_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 0.3789(8) 0.3461(4) 0.4191(7) 0.104(3) Uani 1 1 d . . . . .
H1A H 0.3597 0.3065 0.4246 0.156 Uiso 1 1 calc R U . . .
H1B H 0.4283 0.3519 0.3604 0.156 Uiso 1 1 calc R U . . .
H1C H 0.2937 0.3668 0.4006 0.156 Uiso 1 1 calc R U . . .
C2 C 0.4643(6) 0.3665(3) 0.5309(6) 0.0730(17) Uani 1 1 d . . . . .
H2A H 0.4706 0.4074 0.5279 0.088 Uiso 1 1 calc R U . . .
H2B H 0.4169 0.3572 0.5903 0.088 Uiso 1 1 calc R U . . .
N1 N 0.6065(4) 0.34301(17) 0.5637(4) 0.0509(9) Uani 1 1 d . . . . .
H1 H 0.6560 0.3545 0.5059 0.061 Uiso 1 1 calc R U . . .
C3 C 0.6081(6) 0.2804(2) 0.5703(5) 0.0609(13) Uani 1 1 d . . . . .
H3A H 0.5728 0.2644 0.4950 0.073 Uiso 1 1 calc R U . . .
H3B H 0.5502 0.2677 0.6199 0.073 Uiso 1 1 calc R U . . .
C4 C 0.7541(6) 0.2614(2) 0.6167(4) 0.0554(12) Uani 1 1 d . . . . .
H4A H 0.7566 0.2210 0.6313 0.066 Uiso 1 1 calc R U . . .
H4B H 0.8094 0.2692 0.5619 0.066 Uiso 1 1 calc R U . . .
N2 N 0.8093(4) 0.29243(15) 0.7235(3) 0.0433(8) Uani 1 1 d . . . . .
C5 C 0.8993(5) 0.26843(19) 0.8017(4) 0.0449(10) Uani 1 1 d . . . . .
H5 H 0.9271 0.2322 0.7864 0.054 Uiso 1 1 calc R U . . .
C6 C 0.9620(5) 0.29214(19) 0.9114(4) 0.0427(10) Uani 1 1 d . . . . .
C7 C 0.9297(5) 0.34702(19) 0.9458(4) 0.0425(10) Uani 1 1 d . . . . .
O5 O 0.8503(4) 0.38201(13) 0.8760(3) 0.0511(8) Uani 1 1 d . . . . .
Fe1 Fe 0.72410(7) 0.37319(3) 0.73180(6) 0.04137(18) Uani 1 1 d . . . . .
C8 C 0.9848(5) 0.3634(2) 1.0586(4) 0.0495(11) Uani 1 1 d . . . . .
H8 H 0.9592 0.3980 1.0843 0.059 Uiso 1 1 calc R U . . .
C9 C 1.0757(6) 0.3296(2) 1.1319(4) 0.0532(12) Uani 1 1 d . . . . .
H9 H 1.1124 0.3415 1.2063 0.064 Uiso 1 1 calc R U . . .
C10 C 1.1129(5) 0.2777(2) 1.0956(4) 0.0528(12) Uani 1 1 d . . . . .
Br1 Br 1.24195(7) 0.23188(3) 1.19841(6) 0.0785(2) Uani 1 1 d . . . . .
C11 C 1.0557(5) 0.2584(2) 0.9875(4) 0.0488(11) Uani 1 1 d . . . . .
H11 H 1.0794 0.2228 0.9650 0.059 Uiso 1 1 calc R U . . .
C21 C 1.1115(7) 0.4229(3) 0.6146(7) 0.086(2) Uani 1 1 d . . . . .
H21A H 1.1179 0.4626 0.6326 0.129 Uiso 1 1 calc R U . . .
H21B H 1.0781 0.4181 0.5337 0.129 Uiso 1 1 calc R U . . .
H21C H 1.2009 0.4058 0.6384 0.129 Uiso 1 1 calc R U . . .
C22 C 1.0127(6) 0.3948(3) 0.6763(6) 0.0658(15) Uani 1 1 d . . . . .
H22A H 1.0090 0.3547 0.6588 0.079 Uiso 1 1 calc R U . . .
H22B H 1.0495 0.3988 0.7579 0.079 Uiso 1 1 calc R U . . .
N3 N 0.8708(4) 0.41752(17) 0.6476(3) 0.0473(9) Uani 1 1 d . . . . .
H3 H 0.8356 0.4138 0.5649 0.057 Uiso 1 1 calc R U . . .
C23 C 0.8647(6) 0.4781(2) 0.6767(6) 0.0636(14) Uani 1 1 d . . . . .
H23A H 0.9127 0.5006 0.6307 0.076 Uiso 1 1 calc R U . . .
H23B H 0.9087 0.4841 0.7565 0.076 Uiso 1 1 calc R U . . .
C24 C 0.7167(7) 0.4954(2) 0.6539(6) 0.0705(17) Uani 1 1 d . . . . .
H24A H 0.7092 0.5337 0.6811 0.085 Uiso 1 1 calc R U . . .
H24B H 0.6759 0.4944 0.5726 0.085 Uiso 1 1 calc R U . . .
N4 N 0.6446(4) 0.45565(16) 0.7142(4) 0.0490(9) Uani 1 1 d . . . . .
C25 C 0.5531(5) 0.4747(2) 0.7626(5) 0.0517(11) Uani 1 1 d . . . . .
H25 H 0.5344 0.5133 0.7552 0.062 Uiso 1 1 calc R U . . .
C26 C 0.4761(5) 0.44254(19) 0.8275(4) 0.0459(10) Uani 1 1 d . . . . .
C27 C 0.4900(5) 0.38337(19) 0.8426(4) 0.0447(10) Uani 1 1 d . . . . .
O6 O 0.5720(4) 0.35280(14) 0.7954(3) 0.0553(9) Uani 1 1 d . . . . .
C28 C 0.4106(5) 0.3567(2) 0.9098(5) 0.0524(12) Uani 1 1 d . . . . .
H28 H 0.4195 0.3179 0.9224 0.063 Uiso 1 1 calc R U . . .
C39 C 0.3199(5) 0.3868(2) 0.9575(5) 0.0539(12) Uani 1 1 d . . . . .
H29 H 0.2678 0.3684 1.0013 0.065 Uiso 1 1 calc R U . . .
C30 C 0.3063(5) 0.4447(2) 0.9399(4) 0.0505(11) Uani 1 1 d . . . . .
Br2 Br 0.17993(7) 0.48630(3) 1.00352(6) 0.0736(2) Uani 1 1 d . . . . .
C31 C 0.3822(5) 0.4721(2) 0.8769(5) 0.0513(11) Uani 1 1 d . . . . .
H31 H 0.3720 0.5110 0.8662 0.062 Uiso 1 1 calc R U . . .
Cl1 Cl 0.7701(2) 0.39249(8) 0.32462(14) 0.0875(5) Uani 1 1 d D . . . .
O1 O 0.8027(7) 0.3464(2) 0.3947(6) 0.141(2) Uiso 1 1 d D . . . .
O2 O 0.7125(6) 0.4331(2) 0.3854(5) 0.1133(18) Uiso 1 1 d D . . . .
O3 O 0.8889(7) 0.4147(4) 0.3011(8) 0.202(4) Uiso 1 1 d D . . . .
O4 O 0.6828(8) 0.3803(4) 0.2238(6) 0.188(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.495(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.487(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N1 C3 1.480(7) . ?
N1 Fe1 2.209(4) . ?
N1 H1 0.9800 . ?
C3 C4 1.502(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.472(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N2 C5 1.273(6) . ?
N2 Fe1 2.100(4) . ?
C5 C6 1.437(7) . ?
C5 H5 0.9300 . ?
C6 C11 1.397(7) . ?
C6 C7 1.420(6) . ?
C7 O5 1.307(5) . ?
C7 C8 1.396(7) . ?
O5 Fe1 1.905(3) . ?
Fe1 O6 1.911(3) . ?
Fe1 N4 2.095(4) . ?
Fe1 N3 2.224(4) . ?
C8 C9 1.366(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(7) . ?
C10 Br1 1.903(5) . ?
C11 H11 0.9300 . ?
C21 C22 1.516(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N3 1.478(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N3 C23 1.478(7) . ?
N3 H3 0.9800 . ?
C23 C24 1.493(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 N4 1.472(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
N4 C25 1.273(6) . ?
C25 C26 1.433(7) . ?
C25 H25 0.9300 . ?
C26 C31 1.406(6) . ?
C26 C27 1.412(6) . ?
C27 O6 1.315(5) . ?
C27 C28 1.406(7) . ?
C28 C39 1.375(7) . ?
C28 H28 0.9300 . ?
C39 C30 1.386(7) . ?
C39 H29 0.9300 . ?
C30 C31 1.353(7) . ?
C30 Br2 1.894(5) . ?
C31 H31 0.9300 . ?
Cl1 O4 1.350(6) . ?
Cl1 O1 1.371(5) . ?
Cl1 O3 1.384(6) . ?
Cl1 O2 1.407(5) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 115.3(6) . . ?
N1 C2 H2A 108.4 . . ?
C1 C2 H2A 108.4 . . ?
N1 C2 H2B 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C3 N1 C2 112.7(4) . . ?
C3 N1 Fe1 106.0(3) . . ?
C2 N1 Fe1 113.2(3) . . ?
C3 N1 H1 108.3 . . ?
C2 N1 H1 108.3 . . ?
Fe1 N1 H1 108.3 . . ?
N1 C3 C4 108.5(4) . . ?
N1 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
N1 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
N2 C4 C3 108.0(4) . . ?
N2 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
N2 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C5 N2 C4 118.7(4) . . ?
C5 N2 Fe1 126.4(3) . . ?
C4 N2 Fe1 114.9(3) . . ?
N2 C5 C6 126.0(4) . . ?
N2 C5 H5 117.0 . . ?
C6 C5 H5 117.0 . . ?
C11 C6 C7 119.5(4) . . ?
C11 C6 C5 117.6(4) . . ?
C7 C6 C5 123.0(4) . . ?
O5 C7 C8 119.6(4) . . ?
O5 C7 C6 122.3(4) . . ?
C8 C7 C6 118.1(4) . . ?
C7 O5 Fe1 133.7(3) . . ?
O5 Fe1 O6 94.60(16) . . ?
O5 Fe1 N4 98.34(15) . . ?
O6 Fe1 N4 87.60(15) . . ?
O5 Fe1 N2 87.33(14) . . ?
O6 Fe1 N2 99.04(14) . . ?
N4 Fe1 N2 170.93(15) . . ?
O5 Fe1 N1 165.62(14) . . ?
O6 Fe1 N1 89.06(16) . . ?
N4 Fe1 N1 95.70(16) . . ?
N2 Fe1 N1 78.35(15) . . ?
O5 Fe1 N3 89.93(15) . . ?
O6 Fe1 N3 165.25(15) . . ?
N4 Fe1 N3 77.85(15) . . ?
N2 Fe1 N3 95.18(15) . . ?
N1 Fe1 N3 90.00(15) . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.1(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.8(5) . . ?
C11 C10 Br1 119.8(4) . . ?
C9 C10 Br1 119.4(4) . . ?
C10 C11 C6 120.0(4) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C21 115.0(5) . . ?
N3 C22 H22A 108.5 . . ?
C21 C22 H22A 108.5 . . ?
N3 C22 H22B 108.5 . . ?
C21 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C22 N3 C23 112.7(4) . . ?
C22 N3 Fe1 114.7(3) . . ?
C23 N3 Fe1 106.3(3) . . ?
C22 N3 H3 107.6 . . ?
C23 N3 H3 107.6 . . ?
Fe1 N3 H3 107.6 . . ?
N3 C23 C24 108.3(5) . . ?
N3 C23 H23A 110.0 . . ?
C24 C23 H23A 110.0 . . ?
N3 C23 H23B 110.0 . . ?
C24 C23 H23B 110.0 . . ?
H23A C23 H23B 108.4 . . ?
N4 C24 C23 108.0(4) . . ?
N4 C24 H24A 110.1 . . ?
C23 C24 H24A 110.1 . . ?
N4 C24 H24B 110.1 . . ?
C23 C24 H24B 110.1 . . ?
H24A C24 H24B 108.4 . . ?
C25 N4 C24 118.9(4) . . ?
C25 N4 Fe1 125.2(3) . . ?
C24 N4 Fe1 115.3(3) . . ?
N4 C25 C26 126.3(4) . . ?
N4 C25 H25 116.8 . . ?
C26 C25 H25 116.8 . . ?
C31 C26 C27 119.4(4) . . ?
C31 C26 C25 117.4(4) . . ?
C27 C26 C25 123.1(4) . . ?
O6 C27 C28 119.5(4) . . ?
O6 C27 C26 122.7(4) . . ?
C28 C27 C26 117.8(4) . . ?
C27 O6 Fe1 131.7(3) . . ?
C39 C28 C27 121.4(5) . . ?
C39 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C39 C30 119.8(5) . . ?
C28 C39 H29 120.1 . . ?
C30 C39 H29 120.1 . . ?
C31 C30 C39 120.6(4) . . ?
C31 C30 Br2 119.3(4) . . ?
C39 C30 Br2 120.1(4) . . ?
C30 C31 C26 120.9(5) . . ?
C30 C31 H31 119.5 . . ?
C26 C31 H31 119.5 . . ?
O4 Cl1 O1 113.3(5) . . ?
O4 Cl1 O3 107.5(5) . . ?
O1 Cl1 O3 109.6(5) . . ?
O4 Cl1 O2 110.9(4) . . ?
O1 Cl1 O2 106.8(4) . . ?
O3 Cl1 O2 108.6(4) . . ?

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
C1 C2 N1 C3 -58.1(8) . . . . ?
C1 C2 N1 Fe1 -178.3(5) . . . . ?
C2 N1 C3 C4 -173.6(5) . . . . ?
Fe1 N1 C3 C4 -49.3(5) . . . . ?
N1 C3 C4 N2 52.3(6) . . . . ?
C3 C4 N2 C5 149.1(5) . . . . ?
C3 C4 N2 Fe1 -29.3(5) . . . . ?
C4 N2 C5 C6 -178.9(4) . . . . ?
Fe1 N2 C5 C6 -0.7(7) . . . . ?
N2 C5 C6 C11 177.9(5) . . . . ?
N2 C5 C6 C7 -0.3(7) . . . . ?
C11 C6 C7 O5 175.2(4) . . . . ?
C5 C6 C7 O5 -6.6(7) . . . . ?
C11 C6 C7 C8 -5.2(7) . . . . ?
C5 C6 C7 C8 173.0(4) . . . . ?
C8 C7 O5 Fe1 -163.8(3) . . . . ?
C6 C7 O5 Fe1 15.8(7) . . . . ?
O5 C7 C8 C9 -175.5(5) . . . . ?
C6 C7 C8 C9 4.9(7) . . . . ?
C7 C8 C9 C10 -1.1(8) . . . . ?
C8 C9 C10 C11 -2.6(8) . . . . ?
C8 C9 C10 Br1 179.0(4) . . . . ?
C9 C10 C11 C6 2.1(8) . . . . ?
Br1 C10 C11 C6 -179.4(4) . . . . ?
C7 C6 C11 C10 1.8(7) . . . . ?
C5 C6 C11 C10 -176.5(4) . . . . ?
C21 C22 N3 C23 -61.1(7) . . . . ?
C21 C22 N3 Fe1 177.0(5) . . . . ?
C22 N3 C23 C24 -175.2(5) . . . . ?
Fe1 N3 C23 C24 -48.7(5) . . . . ?
N3 C23 C24 N4 52.7(6) . . . . ?
C23 C24 N4 C25 140.8(5) . . . . ?
C23 C24 N4 Fe1 -30.7(6) . . . . ?
C24 N4 C25 C26 -178.1(5) . . . . ?
Fe1 N4 C25 C26 -7.4(8) . . . . ?
N4 C25 C26 C31 178.2(5) . . . . ?
N4 C25 C26 C27 -2.2(8) . . . . ?
C31 C26 C27 O6 177.4(5) . . . . ?
C25 C26 C27 O6 -2.1(8) . . . . ?
C31 C26 C27 C28 -1.6(7) . . . . ?
C25 C26 C27 C28 178.9(5) . . . . ?
C28 C27 O6 Fe1 -162.8(4) . . . . ?
C26 C27 O6 Fe1 18.2(7) . . . . ?
O6 C27 C28 C39 -177.7(5) . . . . ?
C26 C27 C28 C39 1.4(7) . . . . ?
C27 C28 C39 C30 -0.4(8) . . . . ?
C28 C39 C30 C31 -0.5(8) . . . . ?
C28 C39 C30 Br2 179.2(4) . . . . ?
C39 C30 C31 C26 0.2(8) . . . . ?
Br2 C30 C31 C26 -179.4(4) . . . . ?
C27 C26 C31 C30 0.8(7) . . . . ?
C25 C26 C31 C30 -179.6(5) . . . . ?

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
C2 H2B O6 0.97 2.59 3.133(8) 115.2 .
N1 H1 Cl1 0.98 2.83 3.806(5) 173.5 .
N1 H1 O1 0.98 2.21 3.133(8) 156.9 .
N1 H1 O2 0.98 2.50 3.363(7) 146.7 .
C8 H8 Br2 0.93 3.14 3.911(5) 142.0 3_667
C22 H22A Br1 0.97 3.05 3.738(6) 129.3 4_565
N3 H3 Cl1 0.98 2.86 3.830(4) 171.1 .
N3 H3 O1 0.98 2.56 3.406(8) 145.0 .
N3 H3 O2 0.98 2.27 3.207(7) 159.4 .

_refine_diff_density_max         1.268
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.096

