# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1551122'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;
_chemical_name_common            'Iron-organic Compound'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 Fe N4 O11'
_chemical_formula_weight         528.26

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   13.2018(4)
_cell_length_b                   12.0083(4)
_cell_length_c                   13.7367(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.8500(10)
_cell_angle_gamma                90.00
_cell_volume                     2138.77(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4370
_cell_measurement_theta_min      1.57
_cell_measurement_theta_max      26.37

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Deep Brown'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9127
_exptl_absorpt_correction_T_max  0.9335
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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 SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18829
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4370
_reflns_number_gt                3754
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.3411P] 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     SHELXL
_refine_ls_extinction_coef       0.0054(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4370
_refine_ls_number_parameters     332
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.34083(2) 0.09041(2) 0.83213(2) 0.02296(12) Uani 1 1 d . . .
O1 O 0.31022(14) 0.06450(14) 0.97467(12) 0.0392(4) Uani 1 1 d D . .
O2 O 0.19910(10) 0.01374(12) 0.77161(11) 0.0294(3) Uani 1 1 d . . .
O3 O 0.67004(11) -0.23581(13) 0.89651(12) 0.0381(4) Uani 1 1 d . . .
O4 O 0.27347(10) 0.25070(12) 0.82763(11) 0.0317(3) Uani 1 1 d . . .
O5 O 0.11869(12) -0.14816(14) 0.73510(15) 0.0488(5) Uani 1 1 d . . .
O6 O 0.61241(11) -0.38281(12) 0.80524(11) 0.0294(3) Uani 1 1 d . . .
O7 O 0.30600(16) 0.43042(15) 0.8555(2) 0.0748(8) Uani 1 1 d . . .
O8 O 0.78288(12) 0.11757(14) 0.98045(14) 0.0440(4) Uani 1 1 d . . .
O9 O 0.82357(11) 0.29562(14) 0.99940(14) 0.0443(4) Uani 1 1 d . . .
O100 O 0.13218(13) 0.54429(16) 0.85569(15) 0.0469(4) Uani 1 1 d D . .
O200 O -0.00671(19) 0.57990(19) 0.68786(17) 0.0574(6) Uani 1 1 d . . .
N1 N 0.47050(12) 0.19782(13) 0.90065(12) 0.0236(3) Uani 1 1 d . . .
N2 N 0.38179(12) -0.08511(13) 0.82121(12) 0.0224(3) Uani 1 1 d . . .
C22 C 0.09546(17) 0.38037(19) 1.04875(18) 0.0379(5) Uani 1 1 d . . .
H22A H 0.1431 0.4400 1.0416 0.045 Uiso 1 1 calc R . .
H22B H 0.0318 0.4137 1.0602 0.045 Uiso 1 1 calc R . .
C24 C 0.04948(19) 0.1465(2) 1.05288(18) 0.0410(5) Uani 1 1 d . . .
H24A H 0.1128 0.1119 1.0419 0.049 Uiso 1 1 calc R . .
H24B H 0.0008 0.0879 1.0599 0.049 Uiso 1 1 calc R . .
C1 C 0.33154(16) 0.33203(18) 0.85642(18) 0.0341(5) Uani 1 1 d . . .
C2 C 0.44447(15) 0.30611(16) 0.89426(14) 0.0260(4) Uani 1 1 d . . .
C3 C 0.51656(17) 0.38987(17) 0.91768(17) 0.0343(5) Uani 1 1 d . . .
H3 H 0.4962 0.4641 0.9134 0.041 Uiso 1 1 calc R . .
C4 C 0.61923(16) 0.36223(18) 0.94746(16) 0.0332(5) Uani 1 1 d . . .
H4 H 0.6688 0.4178 0.9624 0.040 Uiso 1 1 calc R . .
C5 C 0.64764(14) 0.25142(17) 0.95490(14) 0.0257(4) Uani 1 1 d . . .
C6 C 0.57019(14) 0.17240(16) 0.93141(14) 0.0249(4) Uani 1 1 d . . .
H6 H 0.5885 0.0976 0.9374 0.030 Uiso 1 1 calc R . .
C7 C 0.75976(15) 0.21761(18) 0.98141(15) 0.0300(5) Uani 1 1 d . . .
C8 C 0.19578(15) -0.09287(16) 0.76279(16) 0.0272(4) Uani 1 1 d . . .
C9 C 0.29987(14) -0.15096(16) 0.79045(13) 0.0227(4) Uani 1 1 d . . .
C10 C 0.30853(15) -0.26483(17) 0.78144(15) 0.0276(4) Uani 1 1 d . . .
H10 H 0.2500 -0.3087 0.7630 0.033 Uiso 1 1 calc R . .
C11 C 0.40526(15) -0.31274(17) 0.80015(15) 0.0272(4) Uani 1 1 d . . .
H11 H 0.4128 -0.3891 0.7927 0.033 Uiso 1 1 calc R . .
C12 C 0.49103(14) -0.24587(16) 0.83019(14) 0.0230(4) Uani 1 1 d . . .
C13 C 0.47480(14) -0.13242(16) 0.84091(14) 0.0246(4) Uani 1 1 d . . .
H13 H 0.5317 -0.0873 0.8629 0.030 Uiso 1 1 calc R . .
C14 C 0.59928(14) -0.29169(16) 0.84606(14) 0.0249(4) Uani 1 1 d . . .
N22 N 0.00654(13) 0.21705(16) 0.96700(14) 0.0331(4) Uani 1 1 d . . .
H22C H -0.0556 0.2428 0.9745 0.040 Uiso 1 1 calc R . .
H22D H -0.0027 0.1754 0.9116 0.040 Uiso 1 1 calc R . .
C23 C 0.07419(17) 0.3126(2) 0.95527(17) 0.0376(5) Uani 1 1 d . . .
H23A H 0.0411 0.3589 0.9006 0.045 Uiso 1 1 calc R . .
H23B H 0.1387 0.2855 0.9401 0.045 Uiso 1 1 calc R . .
N21 N 0.13995(13) 0.30992(16) 1.13416(13) 0.0332(4) Uani 1 1 d . . .
H21A H 0.1504 0.3515 1.1897 0.040 Uiso 1 1 calc R . .
H21B H 0.2015 0.2837 1.1255 0.040 Uiso 1 1 calc R . .
C25 C 0.07129(18) 0.2147(2) 1.14633(17) 0.0401(5) Uani 1 1 d . . .
H25A H 0.0070 0.2424 1.1615 0.048 Uiso 1 1 calc R . .
H25B H 0.1041 0.1683 1.2011 0.048 Uiso 1 1 calc R . .
H1A H 0.319(3) 0.117(2) 1.0261(18) 0.076(10) Uiso 1 1 d D . .
H1B H 0.281(2) -0.0031(16) 0.991(2) 0.076(10) Uiso 1 1 d D . .
H102 H 0.154(3) 0.598(2) 0.894(2) 0.089(13) Uiso 1 1 d D . .
H101 H 0.1863(15) 0.509(2) 0.850(2) 0.057(9) Uiso 1 1 d D . .
H201 H -0.057(3) 0.550(3) 0.694(2) 0.056(9) Uiso 1 1 d . . .
H202 H 0.037(3) 0.574(3) 0.729(3) 0.068(12) Uiso 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 2.0956(16) . ?
Fe1 O2 2.1105(14) . ?
Fe1 O4 2.1164(14) . ?
Fe1 O6 2.1175(14) 2_656 ?
Fe1 N2 2.1881(15) . ?
Fe1 N1 2.2076(16) . ?
O2 C8 1.286(2) . ?
O3 C14 1.249(2) . ?
O4 C1 1.258(3) . ?
O5 C8 1.215(3) . ?
O6 C14 1.256(2) . ?
O6 Fe1 2.1175(14) 2_646 ?
O7 C1 1.228(3) . ?
O8 C7 1.240(3) . ?
O9 C7 1.253(3) . ?
N1 C6 1.339(2) . ?
N1 C2 1.344(3) . ?
N2 C13 1.334(2) . ?
N2 C9 1.342(2) . ?
C22 N21 1.476(3) . ?
C22 C23 1.502(3) . ?
C24 N22 1.476(3) . ?
C24 C25 1.504(3) . ?
C1 C2 1.516(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.388(3) . ?
C5 C7 1.512(3) . ?
C8 C9 1.524(3) . ?
C9 C10 1.380(3) . ?
C10 C11 1.380(3) . ?
C11 C12 1.386(3) . ?
C12 C13 1.391(3) . ?
C12 C14 1.508(2) . ?
N22 C23 1.481(3) . ?
N21 C25 1.488(3) . ?

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 89.47(6) . . ?
O1 Fe1 O4 90.49(6) . . ?
O2 Fe1 O4 92.79(5) . . ?
O1 Fe1 O6 174.26(6) . 2_656 ?
O2 Fe1 O6 95.79(6) . 2_656 ?
O4 Fe1 O6 91.56(6) . 2_656 ?
O1 Fe1 N2 90.84(6) . . ?
O2 Fe1 N2 76.41(6) . . ?
O4 Fe1 N2 169.11(6) . . ?
O6 Fe1 N2 88.16(6) 2_656 . ?
O1 Fe1 N1 87.64(6) . . ?
O2 Fe1 N1 169.01(6) . . ?
O4 Fe1 N1 76.64(6) . . ?
O6 Fe1 N1 87.62(6) 2_656 . ?
N2 Fe1 N1 114.22(6) . . ?
C8 O2 Fe1 118.91(12) . . ?
C1 O4 Fe1 117.96(12) . . ?
C14 O6 Fe1 128.16(13) . 2_646 ?
C6 N1 C2 117.72(16) . . ?
C6 N1 Fe1 129.67(13) . . ?
C2 N1 Fe1 111.67(12) . . ?
C13 N2 C9 118.00(16) . . ?
C13 N2 Fe1 128.78(13) . . ?
C9 N2 Fe1 113.22(12) . . ?
N21 C22 C23 110.58(19) . . ?
N22 C24 C25 110.67(19) . . ?
O7 C1 O4 126.4(2) . . ?
O7 C1 C2 116.8(2) . . ?
O4 C1 C2 116.75(18) . . ?
N1 C2 C3 122.22(18) . . ?
N1 C2 C1 116.36(17) . . ?
C3 C2 C1 121.38(18) . . ?
C2 C3 C4 119.3(2) . . ?
C3 C4 C5 119.44(19) . . ?
C4 C5 C6 117.62(18) . . ?
C4 C5 C7 121.10(18) . . ?
C6 C5 C7 121.17(18) . . ?
N1 C6 C5 123.69(18) . . ?
O8 C7 O9 124.7(2) . . ?
O8 C7 C5 119.29(18) . . ?
O9 C7 C5 116.0(2) . . ?
O5 C8 O2 125.82(19) . . ?
O5 C8 C9 119.40(18) . . ?
O2 C8 C9 114.77(17) . . ?
N2 C9 C10 122.46(17) . . ?
N2 C9 C8 116.37(17) . . ?
C10 C9 C8 121.15(17) . . ?
C9 C10 C11 119.07(18) . . ?
C10 C11 C12 119.30(18) . . ?
C11 C12 C13 117.73(17) . . ?
C11 C12 C14 122.03(17) . . ?
C13 C12 C14 120.17(17) . . ?
N2 C13 C12 123.36(18) . . ?
O3 C14 O6 124.34(18) . . ?
O3 C14 C12 118.27(17) . . ?
O6 C14 C12 117.37(17) . . ?
C24 N22 C23 112.50(17) . . ?
N22 C23 C22 110.26(18) . . ?
C22 N21 C25 111.73(17) . . ?
N21 C25 C24 110.19(18) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.117
