# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            C2/c
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cl2 Fe N10 O12'
_chemical_formula_weight         765.23

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'

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

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

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

_cell_length_a                   17.2679(8)
_cell_length_b                   16.0585(6)
_cell_length_c                   10.7907(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.264(5)
_cell_angle_gamma                90
_cell_volume                     2886.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1956
_cell_measurement_theta_min      3.1976
_cell_measurement_theta_max      29.9636

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.793
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93403
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset), Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16351
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.204
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3312
_reflns_number_gt                2368
_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-2013 (Sheldrick, 2013)'
_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)+(0.0340P)²+2.7280P] 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         3312
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.62320(19) 0.2488(2) 0.0865(3) 0.0257(8) Uani 1 1 d . . . . .
H1 H 0.6290 0.3075 0.0837 0.031 Uiso 1 1 calc R U . . .
C2 C 0.66346(19) 0.1908(2) 0.0262(3) 0.0293(8) Uani 1 1 d . . . . .
H2 H 0.7000 0.2032 -0.0234 0.035 Uiso 1 1 calc R U . . .
C3 C 0.63914(18) 0.1136(2) 0.0539(3) 0.0240(8) Uani 1 1 d . . . . .
H3 H 0.6559 0.0615 0.0280 0.029 Uiso 1 1 calc R U . . .
C4 C 0.54340(17) 0.07072(19) 0.1848(3) 0.0191(7) Uani 1 1 d . . . . .
C5 C 0.54400(17) -0.01519(19) 0.1787(3) 0.0191(7) Uani 1 1 d . . . . .
H5 H 0.5730 -0.0440 0.1284 0.023 Uiso 1 1 calc R U . . .
C6 C 0.5000 -0.0575(3) 0.2500 0.0190(10) Uani 1 2 d S T P . .
C13 C 0.5000 -0.1507(3) 0.2500 0.0178(10) Uani 1 2 d S T P . .
C7 C 0.64085(18) 0.2147(2) 0.5016(3) 0.0238(8) Uani 1 1 d . . . . .
H7 H 0.6488 0.1562 0.5087 0.029 Uiso 1 1 calc R U . . .
C8 C 0.68403(19) 0.2726(2) 0.5894(3) 0.0275(8) Uani 1 1 d . . . . .
H8 H 0.7254 0.2610 0.6650 0.033 Uiso 1 1 calc R U . . .
C9 C 0.65511(18) 0.3488(2) 0.5454(3) 0.0223(7) Uani 1 1 d . . . . .
H9 H 0.6724 0.4010 0.5843 0.027 Uiso 1 1 calc R U . . .
C10 C 0.54857(17) 0.39070(18) 0.3474(3) 0.0162(7) Uani 1 1 d . . . . .
C11 C 0.54863(18) 0.47637(19) 0.3542(3) 0.0183(7) Uani 1 1 d . . . . .
H11 H 0.5804 0.5052 0.4267 0.022 Uiso 1 1 calc R U . . .
C12 C 0.5000 0.5187(3) 0.2500 0.0165(9) Uani 1 2 d S T P . .
C14 C 0.5000 0.6121(3) 0.2500 0.0201(10) Uani 1 2 d S T P . .
N1 N 0.5000 0.1128(2) 0.2500 0.0171(8) Uani 1 2 d S T P . .
N3 N 0.57669(14) 0.21013(15) 0.1466(2) 0.0181(6) Uani 1 1 d . . . . .
N4 N 0.5000 0.3488(2) 0.2500 0.0141(8) Uani 1 2 d S T P . .
N5 N 0.58739(14) 0.25167(15) 0.4070(2) 0.0183(6) Uani 1 1 d . . . . .
N7 N 0.58609(15) 0.12593(15) 0.1260(3) 0.0199(6) Uani 1 1 d . . . . .
N9 N 0.59672(14) 0.33584(15) 0.4353(2) 0.0176(6) Uani 1 1 d . . . . .
O1 O 0.51950(14) -0.18692(14) 0.1587(2) 0.0297(6) Uani 1 1 d . . . . .
H1A H 0.5175 -0.2387 0.1682 0.045 Uiso 0.5 1 calc R U P . .
O1P O 0.77701(16) 0.37281(16) 0.1984(3) 0.0475(7) Uani 1 1 d . . . . .
O2P O 0.65643(13) 0.44978(14) 0.1517(2) 0.0314(6) Uani 1 1 d . . . . .
O3 O 0.50968(14) 0.64859(13) 0.3568(2) 0.0311(6) Uani 1 1 d . . . . .
H3A H 0.5087 0.7004 0.3454 0.047 Uiso 0.5 1 calc R U P . .
O3P O 0.74490(15) 0.45123(17) 0.3600(2) 0.0427(7) Uani 1 1 d . . . . .
O4P O 0.78055(14) 0.51818(15) 0.1893(2) 0.0392(7) Uani 1 1 d . . . . .
Cl1 Cl 0.73947(5) 0.44798(5) 0.22520(8) 0.0246(2) Uani 1 1 d . . . . .
Fe1 Fe 0.5000 0.23021(4) 0.2500 0.01525(18) Uani 1 2 d S T P . .


_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 N3 1.314(4) . ?
C1 C2 1.417(5) . ?
C2 C3 1.368(4) . ?
C3 N7 1.364(4) . ?
C4 N1 1.338(3) . ?
C4 C5 1.381(4) . ?
C4 N7 1.407(4) . ?
C5 C6 1.392(4) . ?
C6 C5 1.392(4) 2_655 ?
C6 C13 1.497(6) . ?
C13 O1 1.264(3) . ?
C13 O1 1.264(3) 2_655 ?
C7 N5 1.323(4) . ?
C7 C8 1.395(5) . ?
C8 C9 1.359(4) . ?
C9 N9 1.357(4) . ?
C10 N4 1.340(3) . ?
C10 C11 1.378(4) . ?
C10 N9 1.397(4) . ?
C11 C12 1.390(3) . ?
C12 C11 1.390(3) 2_655 ?
C12 C14 1.500(6) . ?
C14 O3 1.264(3) . ?
C14 O3 1.264(3) 2_655 ?
N1 C4 1.338(3) 2_655 ?
N1 Fe1 1.886(3) . ?
N3 N7 1.387(3) . ?
N3 Fe1 1.970(3) . ?
N4 C10 1.340(3) 2_655 ?
N4 Fe1 1.904(3) . ?
N5 N9 1.386(3) . ?
N5 Fe1 1.980(2) . ?
O1P Cl1 1.435(3) . ?
O2P Cl1 1.445(2) . ?
O3P Cl1 1.433(3) . ?
O4P Cl1 1.438(2) . ?
Fe1 N3 1.970(3) 2_655 ?
Fe1 N5 1.980(2) 2_655 ?

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
N3 C1 C2 110.7(3) . . ?
C3 C2 C1 106.2(3) . . ?
N7 C3 C2 106.4(3) . . ?
N1 C4 C5 122.8(3) . . ?
N1 C4 N7 110.6(3) . . ?
C5 C4 N7 126.6(3) . . ?
C4 C5 C6 116.7(3) . . ?
C5 C6 C5 121.6(4) . 2_655 ?
C5 C6 C13 119.2(2) . . ?
C5 C6 C13 119.2(2) 2_655 . ?
O1 C13 O1 125.1(4) . 2_655 ?
O1 C13 C6 117.4(2) . . ?
O1 C13 C6 117.4(2) 2_655 . ?
N5 C7 C8 111.4(3) . . ?
C9 C8 C7 106.3(3) . . ?
N9 C9 C8 106.8(3) . . ?
N4 C10 C11 122.3(3) . . ?
N4 C10 N9 110.7(3) . . ?
C11 C10 N9 127.0(3) . . ?
C10 C11 C12 116.9(3) . . ?
C11 C12 C11 121.5(4) 2_655 . ?
C11 C12 C14 119.25(19) 2_655 . ?
C11 C12 C14 119.25(19) . . ?
O3 C14 O3 124.8(4) . 2_655 ?
O3 C14 C12 117.6(2) . . ?
O3 C14 C12 117.6(2) 2_655 . ?
C4 N1 C4 119.4(4) . 2_655 ?
C4 N1 Fe1 120.31(19) . . ?
C4 N1 Fe1 120.31(19) 2_655 . ?
C1 N3 N7 105.6(3) . . ?
C1 N3 Fe1 142.4(2) . . ?
N7 N3 Fe1 112.03(19) . . ?
C10 N4 C10 119.8(3) . 2_655 ?
C10 N4 Fe1 120.12(17) . . ?
C10 N4 Fe1 120.13(17) 2_655 . ?
C7 N5 N9 104.5(2) . . ?
C7 N5 Fe1 143.3(2) . . ?
N9 N5 Fe1 112.13(17) . . ?
C3 N7 N3 111.0(3) . . ?
C3 N7 C4 132.5(3) . . ?
N3 N7 C4 116.4(3) . . ?
C9 N9 N5 111.0(2) . . ?
C9 N9 C10 132.1(3) . . ?
N5 N9 C10 116.8(2) . . ?
O3P Cl1 O1P 108.81(17) . . ?
O3P Cl1 O4P 109.86(16) . . ?
O1P Cl1 O4P 108.90(17) . . ?
O3P Cl1 O2P 110.30(16) . . ?
O1P Cl1 O2P 109.99(15) . . ?
O4P Cl1 O2P 108.96(14) . . ?
N1 Fe1 N4 180.0 . . ?
N1 Fe1 N3 80.58(7) . . ?
N4 Fe1 N3 99.42(7) . . ?
N1 Fe1 N3 80.57(7) . 2_655 ?
N4 Fe1 N3 99.43(7) . 2_655 ?
N3 Fe1 N3 161.15(14) . 2_655 ?
N1 Fe1 N5 100.02(7) . . ?
N4 Fe1 N5 79.98(7) . . ?
N3 Fe1 N5 92.21(10) . . ?
N3 Fe1 N5 91.06(10) 2_655 . ?
N1 Fe1 N5 100.02(7) . 2_655 ?
N4 Fe1 N5 79.98(7) . 2_655 ?
N3 Fe1 N5 91.05(10) . 2_655 ?
N3 Fe1 N5 92.21(10) 2_655 2_655 ?
N5 Fe1 N5 159.95(14) . 2_655 ?

_refine_diff_density_max         0.637
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.092

_shelxl_version_number           2013-4




_database_code_depnum_ccdc_archive 'CCDC 977453'
