# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Arnaud Grosjean'
'Nathalie Daro'
'Brice Kaufmann'
'Abdellak Kaiba'
'Jean-Francois Letard'
'Philippe Guionneau'
_publ_contact_author_name        'Philippe Guionneau'
_publ_contact_author_email       guio@icmcb-bordeaux.cnrs.fr

data_icmcb_16_05_11_0m
_database_code_depnum_ccdc_archive 'CCDC 833475'
#TrackingRef '- FeN03-cifrevision.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
;
X-ray destroyed during data collection. Very weak diffraction
and high fragility of samples.
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H16 Fe N14 O8'
_chemical_formula_weight         468.18

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'
N N 0.0311 0.0180 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.311(2)
_cell_length_b                   10.562(3)
_cell_length_c                   11.339(3)
_cell_angle_alpha                103.765(14)
_cell_angle_beta                 98.100(12)
_cell_angle_gamma                95.523(13)
_cell_volume                     834.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1187
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      35.0

_exptl_crystal_description       needle
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    8.007
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8563
_exptl_absorpt_correction_T_max  0.9242
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
crystal destroyed during data collection. Very weak
diffraction and highly fragile samples.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1187
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0948
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.35
_diffrn_reflns_theta_max         36.38
_reflns_number_total             696
_reflns_number_gt                504
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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^ > 2\s(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^)+(0.1566P)^2^+15.7904P] 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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         696
_refine_ls_number_parameters     115
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0938
_refine_ls_wR_factor_ref         0.2610
_refine_ls_wR_factor_gt          0.2342
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.131(3) 0.337(2) 0.9739(17) 0.017(6) Uiso 1 1 d . . .
N3 N 0.134(3) 0.5681(18) 0.8825(17) 0.007(6) Uiso 1 1 d . . .
N6 N 0.198(3) 0.5885(18) 1.1373(17) 0.009(6) Uiso 1 1 d . . .
N5 N 0.394(3) 0.598(2) 1.1409(18) 0.017(6) Uiso 1 1 d . . .
N4 N 0.331(3) 0.5633(19) 0.8873(18) 0.017(7) Uiso 1 1 d . . .
C8 C 0.075(4) 0.622(2) 0.798(2) 0.008(8) Uiso 1 1 d . . .
H8 H -0.0499 0.6388 0.7788 0.010 Uiso 1 1 calc R . .
C7 C 0.368(3) 0.614(2) 0.794(2) 0.005(7) Uiso 1 1 d . . .
H7 H 0.4868 0.6214 0.7699 0.006 Uiso 1 1 calc R . .
N7 N 0.189(3) 0.1432(18) 0.9425(18) 0.019(6) Uiso 1 1 d D . .
C11 C 0.053(4) 0.218(3) 0.952(2) 0.030(9) Uiso 1 1 d . . .
H11 H -0.0757 0.1893 0.9451 0.036 Uiso 1 1 calc R . .
N10 N 0.195(3) 0.7087(19) 0.6406(18) 0.031(7) Uiso 1 1 d D . .
N8 N 0.167(3) 0.007(2) 0.9124(19) 0.039(7) Uiso 1 1 d D . .
C15 C 0.481(4) 0.669(2) 1.244(2) 0.011(8) Uiso 1 1 d . . .
H15 H 0.6127 0.6859 1.2684 0.013 Uiso 1 1 calc R . .
C14 C 0.184(4) 0.665(2) 1.245(2) 0.012(8) Uiso 1 1 d . . .
H14 H 0.0696 0.6828 1.2711 0.014 Uiso 1 1 calc R . .
N9 N 0.216(3) 0.6518(19) 0.7399(17) 0.022(7) Uiso 1 1 d D . .
N11 N 0.355(3) 0.7142(19) 1.3128(17) 0.029(7) Uiso 1 1 d D . .
N12 N 0.384(3) 0.7980(19) 1.4311(18) 0.029(7) Uiso 1 1 d D . .
O1 O 0.514(3) 0.898(2) 0.8369(18) 0.052(7) Uiso 1 1 d . . .
O2 O 0.665(3) 1.083(2) 0.8444(19) 0.060(7) Uiso 1 1 d . . .
N20 N 0.568(4) 0.978(3) 0.789(3) 0.062(9) Uiso 1 1 d . . .
O3 O 0.526(3) 0.963(2) 0.677(2) 0.086(8) Uiso 1 1 d . . .
O6 O 0.311(3) 0.394(2) 0.544(2) 0.075(7) Uiso 1 1 d . . .
O4 O 0.319(3) 0.321(2) 0.3553(19) 0.058(7) Uiso 1 1 d . . .
O5 O 0.218(3) 0.505(2) 0.423(2) 0.076(8) Uiso 1 1 d . . .
N21 N 0.287(4) 0.411(3) 0.435(3) 0.058(9) Uiso 1 1 d . . .
O7 O 0.879(3) 0.8479(15) 0.3444(15) 0.070(7) Uiso 1 1 d D . .
O8 O 0.939(3) 0.8979(17) 0.6138(14) 0.085(8) Uiso 1 1 d D . .
Fe2 Fe 0.5000 0.5000 1.0000 0.017(2) Uiso 1 2 d S . .
N1 N 0.321(3) 0.3423(19) 0.9782(16) 0.007(6) Uiso 1 1 d . . .
C9 C 0.351(4) 0.223(3) 0.959(2) 0.028(9) Uiso 1 1 d . . .
H9 H 0.4698 0.1939 0.9578 0.034 Uiso 1 1 calc R . .
Fe Fe 0.0000 0.5000 1.0000 0.017(2) Uiso 1 2 d S . .
H3 H 0.4281 0.8791 1.4302 0.020 Uiso 1 1 d D . .
H2 H 0.2614 0.7865 0.6577 0.020 Uiso 1 1 d D . .
H1 H 0.0467 -0.0247 0.9060 0.020 Uiso 1 1 d D . .
H5 H 0.4535 0.7658 1.4838 0.020 Uiso 1 1 d D . .
H6 H 0.2204 0.6533 0.5728 0.020 Uiso 1 1 d D . .
H4 H 0.2343 -0.0228 0.9710 0.020 Uiso 1 1 d D . .
H23 H 0.9137 0.8324 0.4147 0.020 Uiso 1 1 d D . .
H21 H 0.9257 0.8533 0.6669 0.020 Uiso 1 1 d D . .
H24 H 0.9194 0.9291 0.3503 0.020 Uiso 1 1 d D . .
H22 H 0.9459 0.8439 0.5451 0.020 Uiso 1 1 d D . .

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
N2 C11 1.28(3) . ?
N2 N1 1.38(2) . ?
N2 Fe 2.031(19) . ?
N3 C8 1.27(2) . ?
N3 N4 1.44(2) . ?
N3 Fe 1.985(19) . ?
N6 C14 1.31(2) . ?
N6 N5 1.42(2) . ?
N6 Fe 1.951(19) . ?
N5 C15 1.27(3) . ?
N5 Fe2 1.985(19) . ?
N4 C7 1.34(2) . ?
N4 Fe2 1.929(19) . ?
C8 N9 1.35(3) . ?
C7 N9 1.34(2) . ?
N7 C11 1.33(3) . ?
N7 C9 1.34(3) . ?
N7 N8 1.38(3) . ?
N10 N9 1.39(2) . ?
C15 N11 1.34(3) . ?
C14 N11 1.36(3) . ?
N11 N12 1.40(2) . ?
O1 N20 1.18(3) . ?
O2 N20 1.23(3) . ?
N20 O3 1.22(3) . ?
O6 N21 1.29(3) . ?
O4 N21 1.21(3) . ?
O5 N21 1.18(3) . ?
Fe2 N4 1.929(19) 2_667 ?
Fe2 N1 1.96(2) . ?
Fe2 N1 1.96(2) 2_667 ?
Fe2 N5 1.985(19) 2_667 ?
N1 C9 1.28(3) . ?
Fe N6 1.951(19) 2_567 ?
Fe N3 1.985(19) 2_567 ?
Fe N2 2.031(19) 2_567 ?

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
C11 N2 N1 111(2) . . ?
C11 N2 Fe 126(2) . . ?
N1 N2 Fe 123.0(17) . . ?
C8 N3 N4 109(2) . . ?
C8 N3 Fe 130.3(18) . . ?
N4 N3 Fe 120.3(14) . . ?
C14 N6 N5 103(2) . . ?
C14 N6 Fe 128.7(17) . . ?
N5 N6 Fe 128.3(15) . . ?
C15 N5 N6 111(2) . . ?
C15 N5 Fe2 127.9(18) . . ?
N6 N5 Fe2 120.8(16) . . ?
C7 N4 N3 102.7(18) . . ?
C7 N4 Fe2 128.7(17) . . ?
N3 N4 Fe2 128.6(16) . . ?
N3 C8 N9 110(2) . . ?
N4 C7 N9 111(2) . . ?
C11 N7 C9 108(2) . . ?
C11 N7 N8 126(2) . . ?
C9 N7 N8 126(2) . . ?
N2 C11 N7 106(3) . . ?
N5 C15 N11 108(2) . . ?
N6 C14 N11 111(2) . . ?
C7 N9 C8 107(2) . . ?
C7 N9 N10 129(2) . . ?
C8 N9 N10 124(2) . . ?
C15 N11 C14 107(2) . . ?
C15 N11 N12 129(2) . . ?
C14 N11 N12 124(2) . . ?
O1 N20 O3 121(4) . . ?
O1 N20 O2 124(3) . . ?
O3 N20 O2 115(4) . . ?
O5 N21 O4 129(3) . . ?
O5 N21 O6 116(3) . . ?
O4 N21 O6 115(3) . . ?
N4 Fe2 N4 180.000(7) 2_667 . ?
N4 Fe2 N1 89.4(8) 2_667 . ?
N4 Fe2 N1 90.6(8) . . ?
N4 Fe2 N1 90.6(8) 2_667 2_667 ?
N4 Fe2 N1 89.4(8) . 2_667 ?
N1 Fe2 N1 180.000(2) . 2_667 ?
N4 Fe2 N5 89.7(8) 2_667 . ?
N4 Fe2 N5 90.3(8) . . ?
N1 Fe2 N5 92.0(8) . . ?
N1 Fe2 N5 88.0(8) 2_667 . ?
N4 Fe2 N5 90.3(8) 2_667 2_667 ?
N4 Fe2 N5 89.7(8) . 2_667 ?
N1 Fe2 N5 88.0(8) . 2_667 ?
N1 Fe2 N5 92.0(8) 2_667 2_667 ?
N5 Fe2 N5 180.000(7) . 2_667 ?
C9 N1 N2 105(2) . . ?
C9 N1 Fe2 128.5(19) . . ?
N2 N1 Fe2 126.7(15) . . ?
N1 C9 N7 110(2) . . ?
N6 Fe N6 180.000(4) . 2_567 ?
N6 Fe N3 88.7(8) . 2_567 ?
N6 Fe N3 91.3(8) 2_567 2_567 ?
N6 Fe N3 91.3(8) . . ?
N6 Fe N3 88.7(8) 2_567 . ?
N3 Fe N3 180.000(5) 2_567 . ?
N6 Fe N2 89.6(8) . . ?
N6 Fe N2 90.4(8) 2_567 . ?
N3 Fe N2 88.8(8) 2_567 . ?
N3 Fe N2 91.2(8) . . ?
N6 Fe N2 90.4(8) . 2_567 ?
N6 Fe N2 89.6(8) 2_567 2_567 ?
N3 Fe N2 91.2(8) 2_567 2_567 ?
N3 Fe N2 88.8(8) . 2_567 ?
N2 Fe N2 180.000(11) . 2_567 ?

_diffrn_measured_fraction_theta_max 0.871
_diffrn_reflns_theta_full        36.38
_diffrn_measured_fraction_theta_full 0.871
_refine_diff_density_max         0.949
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.138