# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Eunsuk Kim'
'Kelsey Skodje'
'Paul Williard'
_publ_contact_author_email       eunsuk_kim@brown.edu
_publ_contact_author_name        'Eunsuk Kim'

data_esk16may11_0m
_database_code_depnum_ccdc_archive 'CCDC 869734'
#TrackingRef '- esk16may11_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13.50 Fe N4.50 O6.50'
_chemical_formula_weight         416.65

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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                   17.72(3)
_cell_length_b                   12.90(2)
_cell_length_c                   14.74(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.40(3)
_cell_angle_gamma                90.00
_cell_volume                     3361(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          2.00
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1704
_exptl_absorpt_coefficient_mu    0.945
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.2537
_exptl_absorpt_correction_T_max  0.7647
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13820
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         26.12
_reflns_number_total             3314
_reflns_number_gt                2427
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0526P)^2^+1.7554P] where P=(Fo^2^+2Fc^2^)/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         3314
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.113
_refine_ls_shift/su_mean         0.002

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
C1 C 0.48997(17) -0.0049(3) 0.1210(2) 0.0344(8) Uani 1 1 d . . .
H1A H 0.4785 -0.0271 0.1820 0.052 Uiso 1 1 calc R . .
H1B H 0.4660 -0.0525 0.0757 0.052 Uiso 1 1 calc R . .
H1C H 0.4705 0.0654 0.1095 0.052 Uiso 1 1 calc R . .
C2 C 0.57370(18) -0.0057(2) 0.1145(2) 0.0314(7) Uani 1 1 d . . .
C3 C 0.6091(2) -0.0976(3) 0.0922(2) 0.0417(8) Uani 1 1 d . . .
H3 H 0.5805 -0.1598 0.0852 0.050 Uiso 1 1 calc R . .
C4 C 0.6844(2) -0.0985(3) 0.0804(3) 0.0456(9) Uani 1 1 d . . .
H4 H 0.7090 -0.1619 0.0683 0.055 Uiso 1 1 calc R . .
C5 C 0.72562(18) -0.0065(3) 0.0862(2) 0.0358(8) Uani 1 1 d . . .
C6 C 0.80331(19) -0.0008(3) 0.0680(2) 0.0434(9) Uani 1 1 d . . .
H6 H 0.8292 -0.0621 0.0526 0.052 Uiso 1 1 calc R . .
C7 C 0.84022(18) 0.0895(3) 0.0722(2) 0.0443(9) Uani 1 1 d . . .
H7 H 0.8916 0.0919 0.0582 0.053 Uiso 1 1 calc R . .
C8 C 0.80392(17) 0.1816(3) 0.0973(2) 0.0367(8) Uani 1 1 d . . .
C9 C 0.83985(19) 0.2781(3) 0.1022(2) 0.0449(10) Uani 1 1 d . . .
H9 H 0.8910 0.2842 0.0879 0.054 Uiso 1 1 calc R . .
C10 C 0.80172(19) 0.3625(3) 0.1274(2) 0.0433(9) Uani 1 1 d . . .
H10 H 0.8265 0.4279 0.1306 0.052 Uiso 1 1 calc R . .
C11 C 0.72624(18) 0.3555(3) 0.1489(2) 0.0352(8) Uani 1 1 d . . .
C12 C 0.6867(2) 0.4504(3) 0.1763(2) 0.0433(9) Uani 1 1 d . . .
H12A H 0.6465 0.4681 0.1294 0.065 Uiso 1 1 calc R . .
H12B H 0.7229 0.5078 0.1834 0.065 Uiso 1 1 calc R . .
H12C H 0.6644 0.4380 0.2342 0.065 Uiso 1 1 calc R . .
C13 C 0.68824(16) 0.0818(2) 0.1115(2) 0.0290(7) Uani 1 1 d . . .
C14 C 0.72772(17) 0.1787(3) 0.1183(2) 0.0306(7) Uani 1 1 d . . .
C15 C 1.0000 0.1875(5) 0.2500 0.0509(14) Uani 1 2 d S . .
C16 C 1.0000 0.0782(5) 0.2500 0.147(5) Uani 1 2 d S . .
H16A H 1.0521 0.0529 0.2498 0.220 Uiso 0.50 1 calc PR . .
H16B H 0.9703 0.0529 0.1957 0.220 Uiso 0.50 1 calc PR . .
H16C H 0.9776 0.0529 0.3046 0.220 Uiso 0.50 1 calc PR . .
Fe1 Fe 0.57953(2) 0.21828(3) 0.19392(3) 0.02784(16) Uani 1 1 d . . .
N1 N 0.61319(13) 0.08153(19) 0.12718(17) 0.0281(6) Uani 1 1 d . . .
N2 N 0.68988(14) 0.2640(2) 0.14412(17) 0.0292(6) Uani 1 1 d . . .
N3 N 0.66001(17) 0.2199(3) 0.34762(19) 0.0446(8) Uani 1 1 d . . .
N4 N 0.50578(15) 0.3335(2) 0.0758(2) 0.0376(7) Uani 1 1 d . . .
N5 N 1.0000 0.2723(4) 0.2500 0.0828(19) Uani 1 2 d S . .
O1 O 0.5000 0.1765(2) 0.2500 0.0299(7) Uani 1 2 d S . .
O2 O 0.65730(12) 0.13991(19) 0.29937(15) 0.0387(6) Uani 1 1 d . . .
O3 O 0.62424(14) 0.29707(18) 0.31491(15) 0.0405(6) Uani 1 1 d . . .
O4 O 0.6934(2) 0.2214(3) 0.4197(2) 0.1062(14) Uani 1 1 d . . .
O5 O 0.52200(12) 0.24092(17) 0.05827(15) 0.0341(5) Uani 1 1 d . . .
O6 O 0.53140(14) 0.36385(18) 0.15380(17) 0.0425(6) Uani 1 1 d . . .
O7 O 0.47019(14) 0.3897(2) 0.02332(18) 0.0538(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0289(17) 0.0324(19) 0.0418(18) -0.0057(14) 0.0032(15) -0.0065(13)
C2 0.0294(16) 0.0301(18) 0.0343(17) -0.0007(14) 0.0007(14) -0.0005(13)
C3 0.0416(19) 0.032(2) 0.051(2) -0.0033(16) 0.0021(17) 0.0033(16)
C4 0.048(2) 0.037(2) 0.052(2) -0.0016(17) 0.0079(18) 0.0132(17)
C5 0.0315(17) 0.043(2) 0.0333(17) 0.0080(15) 0.0041(14) 0.0117(15)
C6 0.0324(18) 0.056(2) 0.043(2) 0.0141(17) 0.0081(16) 0.0196(18)
C7 0.0209(16) 0.070(3) 0.043(2) 0.0199(18) 0.0084(15) 0.0119(17)
C8 0.0204(15) 0.060(2) 0.0289(16) 0.0129(16) -0.0003(13) -0.0018(15)
C9 0.0229(16) 0.074(3) 0.0371(19) 0.0156(19) 0.0006(14) -0.0142(18)
C10 0.0342(18) 0.057(2) 0.0374(18) 0.0071(17) -0.0037(16) -0.0200(18)
C11 0.0354(18) 0.043(2) 0.0266(16) 0.0040(15) -0.0011(14) -0.0134(16)
C12 0.050(2) 0.041(2) 0.0402(19) -0.0041(16) 0.0073(17) -0.0207(17)
C13 0.0236(15) 0.0370(19) 0.0265(15) 0.0031(13) 0.0024(13) 0.0006(13)
C14 0.0234(15) 0.0440(19) 0.0243(15) 0.0057(14) 0.0003(13) -0.0008(14)
C15 0.050(3) 0.042(3) 0.058(3) 0.000 -0.018(3) 0.000
C16 0.151(9) 0.041(4) 0.229(12) 0.000 -0.110(9) 0.000
Fe1 0.0232(2) 0.0291(3) 0.0318(3) -0.00185(19) 0.00608(18) -0.00336(19)
N1 0.0225(12) 0.0316(15) 0.0300(14) -0.0003(11) 0.0016(11) 0.0009(11)
N2 0.0262(13) 0.0365(16) 0.0251(13) 0.0021(11) 0.0030(11) -0.0063(11)
N3 0.0415(17) 0.064(2) 0.0278(15) 0.0048(16) 0.0012(14) -0.0251(17)
N4 0.0312(15) 0.0397(18) 0.0433(17) 0.0091(14) 0.0112(13) -0.0041(13)
N5 0.107(5) 0.045(3) 0.090(4) 0.000 -0.035(4) 0.000
O1 0.0253(15) 0.0280(16) 0.0375(16) 0.000 0.0097(13) 0.000
O2 0.0319(12) 0.0441(15) 0.0401(13) 0.0036(12) 0.0034(10) -0.0056(11)
O3 0.0478(14) 0.0398(15) 0.0350(12) -0.0040(11) 0.0102(11) -0.0133(12)
O4 0.133(3) 0.127(3) 0.055(2) 0.013(2) -0.020(2) -0.062(3)
O5 0.0328(12) 0.0315(13) 0.0385(13) 0.0005(10) 0.0048(10) 0.0055(10)
O6 0.0475(14) 0.0313(13) 0.0497(15) 0.0002(11) 0.0115(12) -0.0053(11)
O7 0.0499(15) 0.0528(17) 0.0600(16) 0.0292(14) 0.0127(13) 0.0158(13)

_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 1.494(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.331(4) . ?
C2 C3 1.392(5) . ?
C3 C4 1.360(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 C13 1.383(5) . ?
C5 C6 1.425(5) . ?
C6 C7 1.335(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.414(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(5) . ?
C8 C14 1.409(5) . ?
C9 C10 1.348(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(5) . ?
C10 H10 0.9500 . ?
C11 N2 1.343(4) . ?
C11 C12 1.482(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.367(4) . ?
C13 C14 1.433(5) . ?
C14 N2 1.358(4) . ?
C15 N5 1.093(7) . ?
C15 C16 1.410(9) . ?
C16 H16A 0.9805 . ?
C16 H16B 0.9805 . ?
C16 H16C 0.9805 . ?
Fe1 O1 1.772(3) . ?
Fe1 N1 2.127(4) . ?
Fe1 O6 2.127(4) . ?
Fe1 O3 2.151(4) . ?
Fe1 O5 2.194(4) . ?
Fe1 N2 2.221(4) . ?
Fe1 O2 2.238(3) . ?
N3 O4 1.176(5) . ?
N3 O2 1.252(4) . ?
N3 O3 1.257(4) . ?
N4 O7 1.204(4) . ?
N4 O5 1.259(4) . ?
N4 O6 1.266(4) . ?
O1 Fe1 1.772(3) 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
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 C3 120.8(3) . . ?
N1 C2 C1 120.0(3) . . ?
C3 C2 C1 119.2(3) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C13 C5 C4 117.3(3) . . ?
C13 C5 C6 119.9(3) . . ?
C4 C5 C6 122.8(3) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C14 116.9(3) . . ?
C9 C8 C7 123.2(3) . . ?
C14 C8 C7 119.9(3) . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
N2 C11 C10 120.5(3) . . ?
N2 C11 C12 120.3(3) . . ?
C10 C11 C12 119.2(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C5 122.4(3) . . ?
N1 C13 C14 117.8(3) . . ?
C5 C13 C14 119.7(3) . . ?
N2 C14 C8 122.9(3) . . ?
N2 C14 C13 118.5(3) . . ?
C8 C14 C13 118.6(3) . . ?
N5 C15 C16 180.000(1) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.4 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.4 . . ?
H16B C16 H16C 109.4 . . ?
O1 Fe1 N1 103.01(14) . . ?
O1 Fe1 O6 94.69(14) . . ?
N1 Fe1 O6 136.38(13) . . ?
O1 Fe1 O3 90.71(13) . . ?
N1 Fe1 O3 132.59(11) . . ?
O6 Fe1 O3 85.87(14) . . ?
O1 Fe1 O5 97.77(13) . . ?
N1 Fe1 O5 79.39(12) . . ?
O6 Fe1 O5 58.71(9) . . ?
O3 Fe1 O5 144.02(12) . . ?
O1 Fe1 N2 170.85(7) . . ?
N1 Fe1 N2 77.41(13) . . ?
O6 Fe1 N2 91.03(13) . . ?
O3 Fe1 N2 82.58(13) . . ?
O5 Fe1 N2 91.30(14) . . ?
O1 Fe1 O2 90.46(15) . . ?
N1 Fe1 O2 76.54(14) . . ?
O6 Fe1 O2 143.52(10) . . ?
O3 Fe1 O2 57.94(14) . . ?
O5 Fe1 O2 155.75(9) . . ?
N2 Fe1 O2 80.71(14) . . ?
C2 N1 C13 119.1(3) . . ?
C2 N1 Fe1 127.1(2) . . ?
C13 N1 Fe1 112.8(2) . . ?
C11 N2 C14 118.7(3) . . ?
C11 N2 Fe1 130.3(2) . . ?
C14 N2 Fe1 110.1(2) . . ?
O4 N3 O2 121.5(4) . . ?
O4 N3 O3 122.5(4) . . ?
O2 N3 O3 116.0(3) . . ?
O7 N4 O5 123.8(3) . . ?
O7 N4 O6 122.1(3) . . ?
O5 N4 O6 114.1(3) . . ?
Fe1 O1 Fe1 144.6(2) . 2_655 ?
N3 O2 Fe1 91.0(2) . . ?
N3 O3 Fe1 95.0(2) . . ?
N4 O5 Fe1 92.09(18) . . ?
N4 O6 Fe1 95.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.12
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.073