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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_a1
#TrackingRef '1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H19 Fe2 N5 O9'
_chemical_formula_weight         657.16

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   P-1

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

_cell_length_a                   10.4839(18)
_cell_length_b                   11.840(3)
_cell_length_c                   14.034(2)
_cell_angle_alpha                105.645(11)
_cell_angle_beta                 101.222(9)
_cell_angle_gamma                112.358(5)
_cell_volume                     1462.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4114
_cell_measurement_theta_min      3.0055
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668
_exptl_absorpt_coefficient_mu    1.051
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_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            11199
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6486
_reflns_number_gt                5724
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6486
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 -0.18612(3) 1.00651(2) -0.214139(18) 0.01465(10) Uani 1 1 d . . .
Fe2 Fe -0.55220(3) 0.72517(2) -0.308615(18) 0.01479(10) Uani 1 1 d . . .
N1 N 0.04902(18) 1.06856(16) -0.15900(12) 0.0178(3) Uani 1 1 d . . .
C1 C 0.1111(2) 1.10811(18) -0.05513(14) 0.0170(4) Uani 1 1 d . . .
H1A H 0.0513 1.1043 -0.0138 0.020 Uiso 1 1 calc R . .
C2 C 0.2596(2) 1.15451(18) -0.00573(14) 0.0162(3) Uani 1 1 d . . .
C3 C 0.3493(2) 1.1590(2) -0.06714(15) 0.0246(4) Uani 1 1 d . . .
H3A H 0.4498 1.1923 -0.0367 0.030 Uiso 1 1 calc R . .
C5 C 0.1357(2) 1.0692(2) -0.21787(15) 0.0230(4) Uani 1 1 d . . .
H5A H 0.0939 1.0396 -0.2903 0.028 Uiso 1 1 calc R . .
C4 C 0.2843(2) 1.1119(2) -0.17603(16) 0.0295(5) Uani 1 1 d . . .
H4A H 0.3403 1.1093 -0.2197 0.035 Uiso 1 1 calc R . .
O1 O 0.44759(14) 1.25845(13) 0.16001(10) 0.0190(3) Uani 1 1 d . . .
O2 O 0.21583(15) 1.14511(14) 0.15080(10) 0.0202(3) Uani 1 1 d . . .
N3 N -0.72588(18) 0.74846(16) -0.24784(12) 0.0186(3) Uani 1 1 d . . .
C6 C 0.3120(2) 1.18928(18) 0.11118(14) 0.0162(3) Uani 1 1 d . . .
C13 C -0.6945(2) 0.79991(19) -0.14373(14) 0.0189(4) Uani 1 1 d . . .
H13A H -0.5996 0.8292 -0.1009 0.023 Uiso 1 1 calc R . .
C14 C -0.7956(2) 0.81208(18) -0.09595(14) 0.0173(4) Uani 1 1 d . . .
C15 C -0.9361(2) 0.77301(19) -0.15917(14) 0.0198(4) Uani 1 1 d . . .
H15A H -1.0063 0.7802 -0.1299 0.024 Uiso 1 1 calc R . .
N2 N -0.16336(18) 1.16589(16) -0.27049(12) 0.0192(3) Uani 1 1 d . . .
C11 C -0.2400(2) 1.13734(19) -0.36964(14) 0.0197(4) Uani 1 1 d . . .
H11A H -0.2953 1.0491 -0.4144 0.024 Uiso 1 1 calc R . .
C8 C -0.0764(3) 1.3948(2) -0.24012(17) 0.0340(5) Uani 1 1 d . . .
H8A H -0.0186 1.4822 -0.1943 0.041 Uiso 1 1 calc R . .
C7 C -0.0827(2) 1.2936(2) -0.20701(15) 0.0256(4) Uani 1 1 d . . .
H7A H -0.0291 1.3148 -0.1381 0.031 Uiso 1 1 calc R . .
C10 C -0.2405(2) 1.23289(19) -0.40842(14) 0.0209(4) Uani 1 1 d . . .
C9 C -0.1565(3) 1.3649(2) -0.34178(16) 0.0292(5) Uani 1 1 d . . .
H9A H -0.1544 1.4317 -0.3653 0.035 Uiso 1 1 calc R . .
O9 O -0.42541(14) 0.94110(13) -0.25753(10) 0.0178(3) Uani 1 1 d . . .
O8 O -0.60323(15) 0.30250(13) -0.61835(11) 0.0223(3) Uani 1 1 d . . .
O5 O -0.84115(15) 0.87205(14) 0.06435(10) 0.0204(3) Uani 1 1 d . . .
O7 O -0.78934(15) 0.11131(13) -0.63973(10) 0.0194(3) Uani 1 1 d . . .
O3 O -0.33498(16) 1.28485(14) -0.54821(10) 0.0229(3) Uani 1 1 d . . .
O4 O -0.39931(19) 1.07212(15) -0.57653(12) 0.0347(4) Uani 1 1 d . . .
N4 N -0.67302(18) 0.51021(16) -0.36559(12) 0.0187(3) Uani 1 1 d . . .
O6 O -0.61211(16) 0.91699(18) 0.07018(11) 0.0341(4) Uani 1 1 d . . .
C23 C -0.6653(2) 0.43986(18) -0.45485(14) 0.0172(4) Uani 1 1 d . . .
H23A H -0.6142 0.4853 -0.4909 0.021 Uiso 1 1 calc R . .
C18 C -0.7451(2) 0.87117(19) 0.02246(14) 0.0188(4) Uani 1 1 d . . .
C24 C -0.7050(2) 0.23382(18) -0.59311(13) 0.0162(3) Uani 1 1 d . . .
C17 C -0.8627(2) 0.7106(2) -0.30849(14) 0.0215(4) Uani 1 1 d . . .
H17A H -0.8868 0.6748 -0.3810 0.026 Uiso 1 1 calc R . .
C16 C -0.9693(2) 0.7227(2) -0.26769(15) 0.0229(4) Uani 1 1 d . . .
H16A H -1.0619 0.6975 -0.3122 0.027 Uiso 1 1 calc R . .
C12 C -0.3326(2) 1.19203(19) -0.52058(14) 0.0209(4) Uani 1 1 d . . .
C22 C -0.7292(2) 0.30341(19) -0.49636(14) 0.0191(4) Uani 1 1 d . . .
C19 C -0.7485(3) 0.4438(2) -0.31528(17) 0.0290(5) Uani 1 1 d . . .
H19A H -0.7546 0.4911 -0.2531 0.035 Uiso 1 1 calc R . .
C21 C -0.8096(3) 0.2355(2) -0.44433(18) 0.0340(5) Uani 1 1 d . . .
H21A H -0.8567 0.1437 -0.4709 0.041 Uiso 1 1 calc R . .
C20 C -0.8181(3) 0.3071(2) -0.3523(2) 0.0423(7) Uani 1 1 d . . .
H20A H -0.8702 0.2640 -0.3155 0.051 Uiso 1 1 calc R . .
C25 C 0.6694(8) 1.4856(6) -0.0397(6) 0.133(3) Uani 1 1 d . . .
N5 N 0.7302(7) 1.5005(8) 0.0428(5) 0.196(4) Uani 1 1 d . . .
C26 C 0.5926(9) 1.4594(7) -0.1436(5) 0.152(3) Uani 1 1 d . . .
H26A H 0.5692 1.5299 -0.1452 0.228 Uiso 1 1 calc R . .
H26B H 0.5040 1.3779 -0.1700 0.228 Uiso 1 1 calc R . .
H26C H 0.6523 1.4524 -0.1866 0.228 Uiso 1 1 calc R . .

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
Fe1 0.01360(16) 0.01604(16) 0.01017(15) 0.00320(11) 0.00210(10) 0.00483(12)
Fe2 0.01441(16) 0.01576(16) 0.01031(15) 0.00239(11) 0.00298(11) 0.00538(12)
N1 0.0162(7) 0.0203(8) 0.0148(7) 0.0068(6) 0.0040(6) 0.0070(6)
C1 0.0153(9) 0.0195(9) 0.0160(8) 0.0068(7) 0.0052(6) 0.0076(7)
C2 0.0149(9) 0.0170(8) 0.0164(8) 0.0075(7) 0.0039(6) 0.0069(7)
C3 0.0156(9) 0.0364(11) 0.0210(9) 0.0127(8) 0.0058(7) 0.0099(8)
C5 0.0213(10) 0.0309(11) 0.0154(8) 0.0101(8) 0.0064(7) 0.0097(8)
C4 0.0227(10) 0.0494(14) 0.0213(10) 0.0164(9) 0.0127(8) 0.0165(10)
O1 0.0138(6) 0.0236(7) 0.0160(6) 0.0065(5) 0.0024(5) 0.0070(5)
O2 0.0176(7) 0.0254(7) 0.0183(6) 0.0114(5) 0.0059(5) 0.0086(6)
N3 0.0167(8) 0.0186(8) 0.0150(7) 0.0023(6) 0.0026(6) 0.0069(6)
C6 0.0162(8) 0.0173(8) 0.0164(8) 0.0069(7) 0.0045(7) 0.0090(7)
C13 0.0151(9) 0.0214(9) 0.0142(8) 0.0008(7) 0.0020(6) 0.0078(7)
C14 0.0161(9) 0.0161(8) 0.0155(8) 0.0027(6) 0.0037(7) 0.0063(7)
C15 0.0166(9) 0.0216(9) 0.0184(9) 0.0039(7) 0.0055(7) 0.0087(7)
N2 0.0184(8) 0.0181(8) 0.0156(7) 0.0054(6) 0.0013(6) 0.0058(6)
C11 0.0185(9) 0.0169(9) 0.0147(8) 0.0040(7) -0.0001(7) 0.0034(7)
C8 0.0417(13) 0.0165(9) 0.0220(10) 0.0024(8) -0.0047(9) 0.0025(9)
C7 0.0269(10) 0.0213(10) 0.0148(8) 0.0041(7) -0.0032(7) 0.0042(8)
C10 0.0198(9) 0.0207(9) 0.0151(8) 0.0062(7) 0.0010(7) 0.0048(8)
C9 0.0349(12) 0.0188(10) 0.0231(10) 0.0079(8) 0.0011(9) 0.0058(9)
O9 0.0156(6) 0.0172(6) 0.0149(6) 0.0028(5) 0.0021(5) 0.0057(5)
O8 0.0206(7) 0.0192(7) 0.0216(7) 0.0022(5) 0.0114(5) 0.0053(6)
O5 0.0163(6) 0.0281(7) 0.0143(6) 0.0043(5) 0.0052(5) 0.0100(6)
O7 0.0218(7) 0.0164(6) 0.0139(6) 0.0028(5) 0.0054(5) 0.0052(5)
O3 0.0297(8) 0.0220(7) 0.0145(6) 0.0076(5) 0.0032(5) 0.0109(6)
O4 0.0419(10) 0.0209(7) 0.0215(7) 0.0051(6) -0.0091(6) 0.0065(7)
N4 0.0198(8) 0.0174(8) 0.0164(7) 0.0041(6) 0.0074(6) 0.0069(6)
O6 0.0171(7) 0.0504(10) 0.0175(7) -0.0061(6) 0.0007(5) 0.0138(7)
C23 0.0157(8) 0.0183(9) 0.0146(8) 0.0044(7) 0.0058(6) 0.0057(7)
C18 0.0175(9) 0.0195(9) 0.0152(8) 0.0018(7) 0.0027(7) 0.0090(7)
C24 0.0165(8) 0.0165(8) 0.0135(8) 0.0036(6) 0.0038(6) 0.0074(7)
C17 0.0203(9) 0.0251(10) 0.0129(8) 0.0029(7) 0.0019(7) 0.0092(8)
C16 0.0165(9) 0.0282(10) 0.0177(9) 0.0048(8) 0.0004(7) 0.0091(8)
C12 0.0193(9) 0.0221(9) 0.0158(8) 0.0072(7) 0.0019(7) 0.0060(8)
C22 0.0189(9) 0.0196(9) 0.0172(8) 0.0052(7) 0.0076(7) 0.0078(7)
C19 0.0429(13) 0.0238(10) 0.0229(10) 0.0075(8) 0.0207(9) 0.0140(10)
C21 0.0484(14) 0.0166(10) 0.0355(12) 0.0074(9) 0.0277(11) 0.0085(10)
C20 0.0696(19) 0.0252(11) 0.0407(13) 0.0158(10) 0.0417(13) 0.0165(12)
C25 0.102(5) 0.100(4) 0.123(5) 0.042(4) -0.019(4) 0.001(3)
N5 0.107(5) 0.209(8) 0.153(6) 0.095(5) -0.023(4) -0.029(4)
C26 0.175(7) 0.102(5) 0.127(5) 0.027(4) -0.023(5) 0.058(5)

_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 O7 2.0485(13) 2_464 ?
Fe1 O5 2.0955(13) 2_475 ?
Fe1 O2 2.1569(14) 2_575 ?
Fe1 N2 2.1859(17) . ?
Fe1 N1 2.1883(17) . ?
Fe1 O9 2.2220(14) . ?
Fe2 O3 2.0712(13) 2_474 ?
Fe2 O1 2.0784(13) 2_575 ?
Fe2 O8 2.1653(14) 2_464 ?
Fe2 N4 2.1855(17) . ?
Fe2 O9 2.2073(14) . ?
Fe2 N3 2.2312(17) . ?
N1 C1 1.341(2) . ?
N1 C5 1.341(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.390(3) . ?
C2 C6 1.509(2) . ?
C3 C4 1.399(3) . ?
C5 C4 1.383(3) . ?
O1 C6 1.262(2) . ?
O1 Fe2 2.0784(13) 2_575 ?
O2 C6 1.254(2) . ?
O2 Fe1 2.1569(14) 2_575 ?
N3 C13 1.340(2) . ?
N3 C17 1.346(2) . ?
C13 C14 1.390(3) . ?
C14 C15 1.386(3) . ?
C14 C18 1.510(2) . ?
C15 C16 1.393(3) . ?
N2 C11 1.342(2) . ?
N2 C7 1.343(2) . ?
C11 C10 1.382(3) . ?
C8 C9 1.379(3) . ?
C8 C7 1.381(3) . ?
C10 C9 1.392(3) . ?
C10 C12 1.512(2) . ?
O8 C24 1.252(2) . ?
O8 Fe2 2.1653(14) 2_464 ?
O5 C18 1.263(2) . ?
O5 Fe1 2.0955(13) 2_475 ?
O7 C24 1.265(2) . ?
O7 Fe1 2.0485(13) 2_464 ?
O3 C12 1.267(2) . ?
O3 Fe2 2.0712(13) 2_474 ?
O4 C12 1.245(2) . ?
N4 C19 1.337(3) . ?
N4 C23 1.341(2) . ?
O6 C18 1.245(2) . ?
C23 C22 1.384(3) . ?
C24 C22 1.509(2) . ?
C17 C16 1.387(3) . ?
C22 C21 1.390(3) . ?
C19 C20 1.386(3) . ?
C21 C20 1.381(3) . ?
C25 N5 1.138(7) . ?
C25 C26 1.407(8) . ?

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
O7 Fe1 O5 179.46(6) 2_464 2_475 ?
O7 Fe1 O2 94.12(6) 2_464 2_575 ?
O5 Fe1 O2 86.00(6) 2_475 2_575 ?
O7 Fe1 N2 89.48(6) 2_464 . ?
O5 Fe1 N2 90.42(6) 2_475 . ?
O2 Fe1 N2 175.78(6) 2_575 . ?
O7 Fe1 N1 91.87(6) 2_464 . ?
O5 Fe1 N1 87.61(6) 2_475 . ?
O2 Fe1 N1 87.69(6) 2_575 . ?
N2 Fe1 N1 94.41(6) . . ?
O7 Fe1 O9 91.53(5) 2_464 . ?
O5 Fe1 O9 89.00(5) 2_475 . ?
O2 Fe1 O9 88.64(5) 2_575 . ?
N2 Fe1 O9 89.06(6) . . ?
N1 Fe1 O9 175.17(5) . . ?
O3 Fe2 O1 175.79(6) 2_474 2_575 ?
O3 Fe2 O8 86.32(6) 2_474 2_464 ?
O1 Fe2 O8 97.69(6) 2_575 2_464 ?
O3 Fe2 N4 88.48(6) 2_474 . ?
O1 Fe2 N4 93.00(6) 2_575 . ?
O8 Fe2 N4 87.14(6) 2_464 . ?
O3 Fe2 O9 90.16(5) 2_474 . ?
O1 Fe2 O9 88.54(5) 2_575 . ?
O8 Fe2 O9 90.21(5) 2_464 . ?
N4 Fe2 O9 177.09(5) . . ?
O3 Fe2 N3 88.63(6) 2_474 . ?
O1 Fe2 N3 87.38(6) 2_575 . ?
O8 Fe2 N3 174.83(6) 2_464 . ?
N4 Fe2 N3 91.59(6) . . ?
O9 Fe2 N3 90.94(6) . . ?
C1 N1 C5 117.30(17) . . ?
C1 N1 Fe1 115.67(12) . . ?
C5 N1 Fe1 127.02(13) . . ?
N1 C1 C2 123.74(17) . . ?
C1 C2 C3 118.45(17) . . ?
C1 C2 C6 117.54(17) . . ?
C3 C2 C6 123.89(17) . . ?
C2 C3 C4 118.15(19) . . ?
N1 C5 C4 123.12(18) . . ?
C5 C4 C3 119.12(19) . . ?
C6 O1 Fe2 124.37(12) . 2_575 ?
C6 O2 Fe1 126.24(12) . 2_575 ?
C13 N3 C17 117.07(17) . . ?
C13 N3 Fe2 118.31(13) . . ?
C17 N3 Fe2 124.58(13) . . ?
O2 C6 O1 125.93(16) . . ?
O2 C6 C2 116.43(16) . . ?
O1 C6 C2 117.63(16) . . ?
N3 C13 C14 123.87(17) . . ?
C15 C14 C13 118.52(17) . . ?
C15 C14 C18 123.34(17) . . ?
C13 C14 C18 118.11(16) . . ?
C14 C15 C16 118.30(18) . . ?
C11 N2 C7 117.87(17) . . ?
C11 N2 Fe1 119.74(13) . . ?
C7 N2 Fe1 122.22(13) . . ?
N2 C11 C10 123.08(17) . . ?
C9 C8 C7 119.40(19) . . ?
N2 C7 C8 122.53(18) . . ?
C11 C10 C9 118.47(17) . . ?
C11 C10 C12 119.66(17) . . ?
C9 C10 C12 121.86(18) . . ?
C8 C9 C10 118.64(19) . . ?
Fe2 O9 Fe1 112.07(6) . . ?
C24 O8 Fe2 137.02(13) . 2_464 ?
C18 O5 Fe1 128.79(12) . 2_475 ?
C24 O7 Fe1 126.67(12) . 2_464 ?
C12 O3 Fe2 129.11(12) . 2_474 ?
C19 N4 C23 117.64(17) . . ?
C19 N4 Fe2 124.61(13) . . ?
C23 N4 Fe2 117.67(12) . . ?
N4 C23 C22 123.65(17) . . ?
O6 C18 O5 125.72(17) . . ?
O6 C18 C14 117.25(17) . . ?
O5 C18 C14 117.01(16) . . ?
O8 C24 O7 126.79(17) . . ?
O8 C24 C22 116.95(16) . . ?
O7 C24 C22 116.26(16) . . ?
N3 C17 C16 122.96(17) . . ?
C17 C16 C15 119.22(17) . . ?
O4 C12 O3 126.20(17) . . ?
O4 C12 C10 117.89(17) . . ?
O3 C12 C10 115.92(17) . . ?
C23 C22 C21 118.14(17) . . ?
C23 C22 C24 119.52(17) . . ?
C21 C22 C24 122.29(17) . . ?
N4 C19 C20 122.50(19) . . ?
C20 C21 C22 118.6(2) . . ?
C21 C20 C19 119.5(2) . . ?
N5 C25 C26 176.7(9) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.834
_refine_diff_density_rms         0.195
_database_code_depnum_ccdc_archive 'CCDC 930763'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a3
#TrackingRef '3.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H7 Fe N O6'
_chemical_formula_weight         256.99

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   P2(1)/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                   10.996(4)
_cell_length_b                   10.359(4)
_cell_length_c                   7.723(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.018(6)
_cell_angle_gamma                90.00
_cell_volume                     860.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2271
_cell_measurement_theta_min      3.5499
_cell_measurement_theta_max      27.4758

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.984
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    1.762
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3474
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_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  ?
_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            6559
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1951
_reflns_number_gt                1573
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0509P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1951
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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
Fe Fe 0.30352(4) 0.42918(3) 0.84941(5) 0.01105(14) Uani 1 1 d . . .
O1 O 0.14527(19) 1.09477(18) 0.7654(3) 0.0184(4) Uani 1 1 d . . .
O2 O 0.54578(17) 0.90644(17) 0.7810(2) 0.0133(4) Uani 1 1 d . . .
O3 O 0.41188(18) 1.03413(18) 0.6064(3) 0.0180(4) Uani 1 1 d . . .
O4 O 0.15594(18) 1.06691(17) 0.4839(2) 0.0151(4) Uani 1 1 d . . .
O5 O 0.35448(19) 0.23408(17) 0.9196(3) 0.0192(4) Uani 1 1 d . . .
H5C H 0.4283 0.2089 0.9846 0.023 Uiso 1 1 d R . .
H5A H 0.2966 0.1858 0.8783 0.029 Uiso 1 1 d R . .
O6 O 0.16267(18) 0.36248(18) 0.6313(2) 0.0172(4) Uani 1 1 d . . .
H6B H 0.0964 0.3142 0.6413 0.021 Uiso 1 1 d R . .
H6A H 0.1786 0.3877 0.5378 0.026 Uiso 1 1 d R . .
N N 0.2662(2) 0.6292(2) 0.7643(3) 0.0131(5) Uani 1 1 d . . .
C1 C 0.1680(2) 1.0276(3) 0.6422(3) 0.0122(5) Uani 1 1 d . . .
C2 C 0.2078(2) 0.8886(3) 0.6841(3) 0.0122(5) Uani 1 1 d . . .
C3 C 0.1147(3) 0.7988(3) 0.6938(3) 0.0148(6) Uani 1 1 d . . .
H3A H 0.0318 0.8242 0.6747 0.018 Uiso 1 1 calc R . .
C4 C 0.1476(3) 0.6713(3) 0.7325(3) 0.0159(6) Uani 1 1 d . . .
H4A H 0.0849 0.6119 0.7367 0.019 Uiso 1 1 calc R . .
C5 C 0.3555(3) 0.7167(2) 0.7561(3) 0.0129(5) Uani 1 1 d . . .
H5B H 0.4377 0.6889 0.7780 0.016 Uiso 1 1 calc R . .
C6 C 0.3311(2) 0.8467(2) 0.7165(3) 0.0111(5) Uani 1 1 d . . .
C7 C 0.4369(3) 0.9355(2) 0.7009(3) 0.0126(5) 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
Fe 0.0120(2) 0.0072(2) 0.0141(2) -0.00028(13) 0.00299(15) 0.00021(14)
O1 0.0212(12) 0.0145(10) 0.0193(10) -0.0056(7) 0.0040(9) 0.0031(8)
O2 0.0097(10) 0.0126(9) 0.0172(9) 0.0022(7) 0.0021(8) 0.0005(7)
O3 0.0165(11) 0.0112(9) 0.0235(10) 0.0063(7) -0.0024(8) -0.0031(8)
O4 0.0139(11) 0.0155(9) 0.0171(9) 0.0056(7) 0.0060(8) 0.0047(7)
O5 0.0229(12) 0.0107(9) 0.0207(10) 0.0018(7) -0.0036(8) -0.0023(8)
O6 0.0187(11) 0.0141(10) 0.0188(10) 0.0003(7) 0.0038(8) -0.0028(8)
N 0.0122(12) 0.0112(11) 0.0159(11) 0.0016(8) 0.0025(9) 0.0010(9)
C1 0.0070(13) 0.0110(12) 0.0183(13) 0.0009(10) 0.0020(10) -0.0029(10)
C2 0.0145(14) 0.0108(12) 0.0112(12) 0.0006(9) 0.0026(11) 0.0011(10)
C3 0.0113(14) 0.0132(12) 0.0200(13) 0.0033(10) 0.0033(11) 0.0015(10)
C4 0.0133(14) 0.0126(13) 0.0214(13) 0.0025(10) 0.0025(11) -0.0022(10)
C5 0.0131(14) 0.0105(12) 0.0148(12) 0.0014(9) 0.0021(11) 0.0007(10)
C6 0.0121(13) 0.0086(11) 0.0128(11) -0.0003(9) 0.0029(10) -0.0011(10)
C7 0.0149(14) 0.0090(12) 0.0131(12) -0.0020(9) 0.0016(10) -0.0007(10)

_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
Fe O4 2.101(2) 4_576 ?
Fe O2 2.1238(19) 2_646 ?
Fe O3 2.126(2) 4_576 ?
Fe O5 2.1367(19) . ?
Fe O6 2.151(2) . ?
Fe N 2.187(2) . ?
O1 C1 1.246(3) . ?
O2 C7 1.264(3) . ?
O2 Fe 2.1238(19) 2_656 ?
O3 C7 1.253(3) . ?
O3 Fe 2.126(2) 4_575 ?
O4 C1 1.269(3) . ?
O4 Fe 2.101(2) 4_575 ?
N C5 1.348(3) . ?
N C4 1.347(3) . ?
C1 C2 1.520(4) . ?
C2 C3 1.398(4) . ?
C2 C6 1.395(4) . ?
C3 C4 1.386(4) . ?
C5 C6 1.395(3) . ?
C6 C7 1.507(4) . ?

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
O4 Fe O2 174.62(7) 4_576 2_646 ?
O4 Fe O3 82.85(8) 4_576 4_576 ?
O2 Fe O3 96.97(8) 2_646 4_576 ?
O4 Fe O5 94.68(8) 4_576 . ?
O2 Fe O5 79.99(7) 2_646 . ?
O3 Fe O5 82.29(8) 4_576 . ?
O4 Fe O6 83.64(8) 4_576 . ?
O2 Fe O6 95.66(8) 2_646 . ?
O3 Fe O6 163.92(8) 4_576 . ?
O5 Fe O6 90.17(8) . . ?
O4 Fe N 90.82(8) 4_576 . ?
O2 Fe N 94.52(7) 2_646 . ?
O3 Fe N 98.33(8) 4_576 . ?
O5 Fe N 174.50(8) . . ?
O6 Fe N 90.54(8) . . ?
C7 O2 Fe 119.64(16) . 2_656 ?
C7 O3 Fe 134.61(18) . 4_575 ?
C1 O4 Fe 123.08(18) . 4_575 ?
C5 N C4 117.4(2) . . ?
C5 N Fe 123.92(18) . . ?
C4 N Fe 118.38(17) . . ?
O1 C1 O4 124.0(2) . . ?
O1 C1 C2 117.5(2) . . ?
O4 C1 C2 118.5(2) . . ?
C3 C2 C6 118.6(2) . . ?
C3 C2 C1 117.4(2) . . ?
C6 C2 C1 124.0(2) . . ?
C4 C3 C2 119.0(3) . . ?
N C4 C3 123.2(2) . . ?
N C5 C6 123.4(2) . . ?
C5 C6 C2 118.4(2) . . ?
C5 C6 C7 119.3(2) . . ?
C2 C6 C7 122.2(2) . . ?
O3 C7 O2 123.4(2) . . ?
O3 C7 C6 117.7(2) . . ?
O2 C7 C6 119.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.039
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.130
_database_code_depnum_ccdc_archive 'CCDC 930765'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a4
#TrackingRef '4.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H7 Fe N O7'
_chemical_formula_weight         272.99

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   P-1

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

_cell_length_a                   7.137(3)
_cell_length_b                   7.968(3)
_cell_length_c                   9.108(4)
_cell_angle_alpha                75.892(17)
_cell_angle_beta                 68.644(15)
_cell_angle_gamma                76.345(16)
_cell_volume                     461.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1428
_cell_measurement_theta_min      3.1062
_cell_measurement_theta_max      27.4719

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.3000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.1500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.964
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8162
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_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  ?
_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            2937
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1553
_reflns_number_gt                1460
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1553
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Fe Fe 0.47880(5) 0.25603(4) 0.21794(4) 0.0140(2) Uani 1 1 d . . .
O1 O 1.2469(3) -0.5082(3) 0.2210(2) 0.0169(5) Uani 1 1 d . . .
O2 O 1.4349(3) -0.3049(2) 0.0541(2) 0.0158(5) Uani 1 1 d . . .
O3 O 1.2686(3) 0.1122(3) 0.2391(3) 0.0258(5) Uani 1 1 d . . .
O4 O 1.3036(3) -0.1619(3) 0.3770(2) 0.0223(5) Uani 1 1 d . . .
O5 O 0.4085(4) 0.2521(4) 0.4645(3) 0.0252(6) Uani 1 1 d . . .
O6 O 0.6917(4) 0.4306(3) 0.1629(3) 0.0192(5) Uani 1 1 d . . .
N N 0.7293(4) 0.0389(3) 0.2104(3) 0.0132(5) Uani 1 1 d . . .
C1 C 1.2685(4) -0.3537(3) 0.1476(3) 0.0125(6) Uani 1 1 d . . .
C2 C 1.2247(4) -0.0407(4) 0.2931(3) 0.0151(6) Uani 1 1 d . . .
C3 C 0.8813(4) 0.0484(3) 0.2595(3) 0.0150(6) Uani 1 1 d . . .
C4 C 1.0579(4) -0.0740(3) 0.2433(3) 0.0115(6) Uani 1 1 d . . .
C5 C 1.0789(4) -0.2179(3) 0.1739(3) 0.0129(6) Uani 1 1 d . . .
C6 C 0.9239(4) -0.2284(3) 0.1202(3) 0.0148(6) Uani 1 1 d . . .
C7 C 0.7542(4) -0.0988(3) 0.1389(3) 0.0148(6) Uani 1 1 d . . .
O7 O 0.8347(3) 0.4504(3) 0.4057(2) 0.0244(5) Uani 1 1 d . . .
H6 H 0.936(4) -0.317(4) 0.069(4) 0.010(7) Uiso 1 1 d . . .
H3 H 0.860(5) 0.136(4) 0.315(4) 0.020(8) Uiso 1 1 d . . .
H7 H 0.652(5) -0.095(4) 0.101(4) 0.019(8) Uiso 1 1 d . . .
H9B H 0.721(6) 0.438(5) 0.218(5) 0.026(13) Uiso 1 1 d . . .
H10B H 0.471(7) 0.207(5) 0.512(5) 0.034(12) Uiso 1 1 d . . .
H10A H 0.343(7) 0.321(5) 0.493(5) 0.028(13) Uiso 1 1 d . . .
H9A H 0.639(6) 0.511(5) 0.136(5) 0.025(11) Uiso 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
Fe 0.0128(3) 0.0104(3) 0.0199(3) -0.0029(2) -0.0069(2) -0.0010(2)
O1 0.0142(11) 0.0098(9) 0.0230(11) -0.0009(8) -0.0045(9) 0.0006(8)
O2 0.0117(11) 0.0159(10) 0.0178(11) -0.0010(8) -0.0040(9) -0.0016(8)
O3 0.0248(13) 0.0149(10) 0.0444(14) -0.0006(9) -0.0181(11) -0.0092(9)
O4 0.0213(12) 0.0227(11) 0.0256(12) 0.0036(9) -0.0149(10) -0.0049(9)
O5 0.0252(15) 0.0276(14) 0.0218(13) -0.0056(11) -0.0110(12) 0.0042(11)
O6 0.0209(13) 0.0138(12) 0.0276(14) -0.0012(10) -0.0156(11) -0.0014(10)
N 0.0103(12) 0.0131(11) 0.0154(12) -0.0016(9) -0.0044(10) -0.0009(9)
C1 0.0159(15) 0.0114(13) 0.0135(14) -0.0044(10) -0.0079(12) -0.0010(11)
C2 0.0105(15) 0.0170(14) 0.0175(15) -0.0072(11) -0.0031(13) 0.0005(11)
C3 0.0190(17) 0.0119(13) 0.0150(14) -0.0008(11) -0.0074(13) -0.0028(11)
C4 0.0108(14) 0.0101(12) 0.0118(13) 0.0015(10) -0.0027(11) -0.0035(11)
C5 0.0125(15) 0.0111(12) 0.0110(13) 0.0010(10) -0.0003(12) -0.0027(11)
C6 0.0178(16) 0.0125(13) 0.0156(14) -0.0030(11) -0.0064(13) -0.0035(11)
C7 0.0107(15) 0.0170(14) 0.0162(14) 0.0003(11) -0.0050(12) -0.0033(11)
O7 0.0250(13) 0.0223(11) 0.0249(12) -0.0030(9) -0.0086(10) -0.0025(9)

_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
Fe O3 2.023(2) 1_455 ?
Fe O5 2.109(3) . ?
Fe O6 2.145(2) . ?
Fe N 2.168(2) . ?
Fe O1 2.189(2) 1_465 ?
Fe O2 2.280(2) 2_755 ?
O1 C1 1.264(3) . ?
O1 Fe 2.189(2) 1_645 ?
O2 C1 1.268(3) . ?
O2 Fe 2.280(2) 2_755 ?
O3 C2 1.265(3) . ?
O3 Fe 2.023(2) 1_655 ?
O4 C2 1.237(3) . ?
O5 H10B 0.70(4) . ?
O5 H10A 0.67(4) . ?
O6 H9B 0.63(4) . ?
O6 H9A 0.70(4) . ?
N C3 1.338(4) . ?
N C7 1.354(4) . ?
C1 C5 1.503(4) . ?
C2 C4 1.515(4) . ?
C3 C4 1.384(4) . ?
C3 H3 0.91(4) . ?
C4 C5 1.392(4) . ?
C5 C6 1.388(4) . ?
C6 C7 1.381(4) . ?
C6 H6 0.91(3) . ?
C7 H7 0.91(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
O3 Fe O5 97.03(10) 1_455 . ?
O3 Fe O6 171.22(10) 1_455 . ?
O5 Fe O6 90.10(10) . . ?
O3 Fe N 96.32(9) 1_455 . ?
O5 Fe N 93.47(11) . . ?
O6 Fe N 88.33(10) . . ?
O3 Fe O1 89.15(9) 1_455 1_465 ?
O5 Fe O1 86.35(10) . 1_465 ?
O6 Fe O1 86.18(9) . 1_465 ?
N Fe O1 174.51(7) . 1_465 ?
O3 Fe O2 90.57(8) 1_455 2_755 ?
O5 Fe O2 170.75(9) . 2_755 ?
O6 Fe O2 81.89(9) . 2_755 ?
N Fe O2 90.92(8) . 2_755 ?
O1 Fe O2 88.50(8) 1_465 2_755 ?
C1 O1 Fe 128.75(19) . 1_645 ?
C1 O2 Fe 123.13(16) . 2_755 ?
C2 O3 Fe 141.11(19) . 1_655 ?
Fe O5 H10B 126(4) . . ?
Fe O5 H10A 116(3) . . ?
H10B O5 H10A 114(5) . . ?
Fe O6 H9B 119(4) . . ?
Fe O6 H9A 102(3) . . ?
H9B O6 H9A 110(5) . . ?
C3 N C7 116.9(2) . . ?
C3 N Fe 119.78(19) . . ?
C7 N Fe 122.80(18) . . ?
O1 C1 O2 125.7(3) . . ?
O1 C1 C5 116.5(2) . . ?
O2 C1 C5 117.8(2) . . ?
O4 C2 O3 127.7(2) . . ?
O4 C2 C4 118.4(2) . . ?
O3 C2 C4 113.9(2) . . ?
N C3 C4 124.1(3) . . ?
N C3 H3 117(2) . . ?
C4 C3 H3 119(2) . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 C2 118.7(2) . . ?
C5 C4 C2 122.8(2) . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 C1 121.7(2) . . ?
C6 C5 C1 120.0(2) . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 119.7(19) . . ?
C5 C6 H6 120.7(19) . . ?
N C7 C6 122.8(3) . . ?
N C7 H7 114(2) . . ?
C6 C7 H7 123(2) . . ?

_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 930766'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a5
#TrackingRef '5.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H4 Fe N2 O4'
_chemical_formula_weight         259.99

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   'P 21/n'

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

_cell_length_a                   10.1761(9)
_cell_length_b                   5.9639(5)
_cell_length_c                   13.3111(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.591(6)
_cell_angle_gamma                90.00
_cell_volume                     802.50(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_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            6021
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1826
_reflns_number_gt                1584
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1826
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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 0.75253(4) 0.21778(6) 0.82831(3) 0.00971(18) Uani 1 1 d . . .
O1 O 0.42406(18) 0.1288(3) 1.28385(14) 0.0115(4) Uani 1 1 d . . .
O2 O 0.3891(2) -0.0072(3) 1.12696(15) 0.0153(4) Uani 1 1 d . . .
O3 O 0.35183(18) 0.5683(3) 1.27666(14) 0.0107(4) Uani 1 1 d . . .
N1 N 0.7650(2) 0.4076(4) 0.96214(17) 0.0109(5) Uani 1 1 d . . .
N2 N 0.8106(2) 0.7169(4) 1.05259(18) 0.0115(5) Uani 1 1 d . . .
H2A H 0.8470 0.8426 1.0712 0.014 Uiso 1 1 calc R . .
C6 C 0.5586(3) 0.5035(4) 1.20986(19) 0.0097(5) Uani 1 1 d . . .
C8 C 0.7155(2) 0.6057(4) 1.0994(2) 0.0102(5) Uani 1 1 d . . .
C4 C 0.5968(3) 0.2541(5) 1.0709(2) 0.0094(5) Uani 1 1 d . . .
C7 C 0.6525(3) 0.6563(5) 1.1838(2) 0.0111(5) Uani 1 1 d . . .
C9 C 0.4423(2) 0.1304(4) 1.1912(2) 0.0101(5) Uani 1 1 d . . .
C5 C 0.5330(3) 0.3025(4) 1.1549(2) 0.0093(5) Uani 1 1 d . . .
C2 C 0.6874(3) 0.4097(5) 1.04241(19) 0.0092(5) Uani 1 1 d . . .
C1 C 0.8357(3) 0.5944(5) 0.9736(2) 0.0122(5) Uani 1 1 d . . .
O4 O 0.53958(19) 0.5953(3) 1.38105(14) 0.0135(4) Uani 1 1 d . . .
C10 C 0.4822(3) 0.5597(4) 1.2966(2) 0.0094(5) Uani 1 1 d . . .
H4 H 0.579(3) 0.140(5) 1.037(2) 0.004(7) Uiso 1 1 d . . .
H3 H 0.674(4) 0.790(6) 1.221(3) 0.026(11) Uiso 1 1 d . . .
H1 H 0.879(4) 0.627(7) 0.941(3) 0.031(12) Uiso 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
Fe1 0.0058(3) 0.0118(3) 0.0115(3) -0.00001(13) 0.00105(17) -0.00075(13)
O1 0.0074(9) 0.0150(10) 0.0122(9) 0.0011(7) 0.0010(7) 0.0012(7)
O2 0.0146(10) 0.0158(10) 0.0167(10) -0.0051(8) 0.0067(8) -0.0082(8)
O3 0.0043(9) 0.0131(9) 0.0145(9) 0.0009(7) 0.0004(7) 0.0009(7)
N1 0.0054(10) 0.0171(11) 0.0103(10) 0.0008(9) 0.0019(8) -0.0028(8)
N2 0.0068(12) 0.0134(12) 0.0143(12) -0.0005(8) 0.0005(10) -0.0063(8)
C6 0.0055(11) 0.0127(12) 0.0103(12) 0.0003(10) -0.0016(9) 0.0018(9)
C8 0.0051(11) 0.0134(13) 0.0117(12) 0.0003(10) -0.0009(9) -0.0032(9)
C4 0.0047(13) 0.0113(12) 0.0120(13) -0.0036(10) 0.0007(10) -0.0025(9)
C7 0.0074(12) 0.0128(12) 0.0126(12) -0.0036(10) -0.0015(10) -0.0028(10)
C9 0.0045(11) 0.0121(12) 0.0141(13) -0.0013(10) 0.0026(9) 0.0016(9)
C5 0.0032(12) 0.0137(13) 0.0110(13) -0.0011(10) 0.0007(10) -0.0016(9)
C2 0.0058(11) 0.0139(12) 0.0077(11) -0.0013(9) 0.0002(9) 0.0006(9)
C1 0.0070(12) 0.0193(13) 0.0105(13) 0.0031(11) 0.0013(10) -0.0038(10)
O4 0.0108(9) 0.0171(10) 0.0117(9) -0.0034(7) -0.0032(7) 0.0047(8)
C10 0.0072(12) 0.0060(11) 0.0147(12) 0.0012(10) 0.0008(10) 0.0007(9)

_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 O2 2.051(2) 3_657 ?
Fe1 O3 2.0897(19) 3_667 ?
Fe1 N1 2.102(2) . ?
Fe1 O1 2.1145(19) 4_665 ?
Fe1 O3 2.1365(19) 4_665 ?
O1 C9 1.268(3) . ?
O1 Fe1 2.1145(19) 4_566 ?
O2 C9 1.262(3) . ?
O2 Fe1 2.051(2) 3_657 ?
O3 C10 1.323(3) . ?
O3 Fe1 2.0897(19) 3_667 ?
O3 Fe1 2.1365(19) 4_566 ?
N1 C1 1.325(4) . ?
N1 C2 1.399(3) . ?
N2 C1 1.330(4) . ?
N2 C8 1.379(3) . ?
C6 C7 1.393(4) . ?
C6 C5 1.413(4) . ?
C6 C10 1.502(4) . ?
C8 C7 1.390(4) . ?
C8 C2 1.405(4) . ?
C4 C5 1.386(4) . ?
C4 C2 1.392(4) . ?
C9 C5 1.498(4) . ?
O4 C10 1.225(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
O2 Fe1 O3 104.34(8) 3_657 3_667 ?
O2 Fe1 N1 93.42(8) 3_657 . ?
O3 Fe1 N1 102.39(8) 3_667 . ?
O2 Fe1 O1 167.54(8) 3_657 4_665 ?
O3 Fe1 O1 85.48(7) 3_667 4_665 ?
N1 Fe1 O1 91.88(8) . 4_665 ?
O2 Fe1 O3 88.78(8) 3_657 4_665 ?
O3 Fe1 O3 119.68(4) 3_667 4_665 ?
N1 Fe1 O3 135.89(8) . 4_665 ?
O1 Fe1 O3 79.59(7) 4_665 4_665 ?
C9 O1 Fe1 119.12(16) . 4_566 ?
C9 O2 Fe1 117.54(17) . 3_657 ?
C10 O3 Fe1 125.34(16) . 3_667 ?
C10 O3 Fe1 113.87(15) . 4_566 ?
Fe1 O3 Fe1 118.68(8) 3_667 4_566 ?
C1 N1 C2 104.5(2) . . ?
C1 N1 Fe1 121.94(19) . . ?
C2 N1 Fe1 131.88(18) . . ?
C1 N2 C8 107.5(2) . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 C10 118.4(2) . . ?
C5 C6 C10 120.4(2) . . ?
N2 C8 C7 132.3(2) . . ?
N2 C8 C2 105.5(2) . . ?
C7 C8 C2 122.2(2) . . ?
C5 C4 C2 117.9(2) . . ?
C8 C7 C6 116.9(2) . . ?
O2 C9 O1 123.7(2) . . ?
O2 C9 C5 117.3(2) . . ?
O1 C9 C5 118.9(2) . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 C9 118.7(2) . . ?
C6 C5 C9 119.9(2) . . ?
C4 C2 N1 130.7(3) . . ?
C4 C2 C8 120.5(2) . . ?
N1 C2 C8 108.8(2) . . ?
N1 C1 N2 113.7(3) . . ?
O4 C10 O3 122.6(2) . . ?
O4 C10 C6 120.6(2) . . ?
O3 C10 C6 116.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.728
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.194
_database_code_depnum_ccdc_archive 'CCDC 930767'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a6
#TrackingRef '6.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 Fe N2 O5'
_chemical_formula_weight         278.01

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'
Fe Fe 0.3463 0.8444 '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'

_symmetry_cell_setting           ?
_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                   9.345(9)
_cell_length_b                   6.916(4)
_cell_length_c                   14.615(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.44(5)
_cell_angle_gamma                90.00
_cell_volume                     914.7(12)
_cell_formula_units_Z            4
_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          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    1.661
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6734
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2050
_reflns_number_gt                1804
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2050
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.39173(4) -0.31614(5) 0.52139(2) 0.01125(17) Uani 1 1 d . . .
O4 O 0.3562(2) -0.2057(2) 0.38187(13) 0.0141(4) Uani 1 1 d . . .
O3 O 0.31174(19) 0.0160(3) 0.26779(12) 0.0178(4) Uani 1 1 d . . .
O5 O 0.4801(2) -0.4697(3) 0.65029(12) 0.0200(4) Uani 1 1 d . . .
H5A H 0.4431 -0.5942 0.6595 0.024 Uiso 1 1 calc R . .
H5B H 0.5563 -0.4133 0.6983 0.024 Uiso 1 1 calc R . .
O2 O 0.2501(2) 0.4719(2) 0.46803(13) 0.0194(4) Uani 1 1 d . . .
O1 O 0.39576(19) 0.2187(3) 0.45817(12) 0.0167(4) Uani 1 1 d . . .
N2 N -0.2684(2) 0.1351(3) 0.40685(13) 0.0124(4) Uani 1 1 d . . .
N1 N -0.2458(2) -0.1394(3) 0.33116(14) 0.0146(4) Uani 1 1 d . . .
H1B H -0.2705 -0.2497 0.3014 0.017 Uiso 1 1 calc R . .
C3 C 0.1350(3) 0.1774(3) 0.41224(17) 0.0102(5) Uani 1 1 d . . .
C5 C -0.1219(2) 0.1187(3) 0.39842(15) 0.0100(4) Uani 1 1 d . . .
C6 C -0.1091(2) -0.0547(3) 0.35147(15) 0.0118(5) Uani 1 1 d . . .
C9 C 0.2705(3) 0.2988(3) 0.44812(17) 0.0135(5) Uani 1 1 d . . .
C8 C 0.2835(2) -0.0651(3) 0.33790(15) 0.0112(4) Uani 1 1 d . . .
C2 C 0.1451(2) 0.0004(3) 0.36520(15) 0.0101(4) Uani 1 1 d . . .
C7 C -0.3356(3) -0.0218(4) 0.36529(16) 0.0150(5) Uani 1 1 d . . .
H7A H -0.4370 -0.0490 0.3600 0.018 Uiso 1 1 calc R . .
C4 C 0.0007(3) 0.2366(3) 0.42884(16) 0.0124(5) Uani 1 1 d . . .
H4A H -0.0064 0.3551 0.4603 0.015 Uiso 1 1 calc R . .
C1 C 0.0232(3) -0.1176(3) 0.33400(16) 0.0128(4) Uani 1 1 d . . .
H1A H 0.0294 -0.2360 0.3022 0.015 Uiso 1 1 calc R . .

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
Fe1 0.0094(2) 0.0121(2) 0.0124(2) -0.00088(11) 0.00293(16) -0.00086(11)
O4 0.0114(9) 0.0163(8) 0.0154(9) 0.0030(6) 0.0051(7) 0.0029(6)
O3 0.0161(9) 0.0228(9) 0.0168(9) 0.0067(7) 0.0085(7) 0.0050(7)
O5 0.0202(9) 0.0251(10) 0.0160(8) 0.0054(7) 0.0069(7) 0.0039(7)
O2 0.0172(9) 0.0137(8) 0.0262(10) -0.0036(7) 0.0035(8) -0.0053(7)
O1 0.0090(8) 0.0212(8) 0.0196(9) -0.0003(7) 0.0028(7) -0.0036(7)
N2 0.0089(10) 0.0155(9) 0.0129(9) 0.0003(8) 0.0029(7) -0.0001(8)
N1 0.0086(9) 0.0178(9) 0.0171(10) -0.0077(8) 0.0029(8) -0.0040(8)
C3 0.0076(11) 0.0127(11) 0.0095(10) 0.0003(7) 0.0008(9) -0.0028(8)
C5 0.0084(10) 0.0130(11) 0.0088(9) 0.0012(8) 0.0026(8) 0.0017(8)
C6 0.0104(11) 0.0136(11) 0.0112(10) -0.0006(8) 0.0027(8) -0.0025(8)
C9 0.0145(12) 0.0155(11) 0.0103(10) 0.0011(8) 0.0028(9) -0.0041(8)
C8 0.0075(10) 0.0149(10) 0.0112(10) -0.0005(8) 0.0024(8) -0.0007(8)
C2 0.0074(10) 0.0140(11) 0.0096(10) 0.0015(8) 0.0032(8) 0.0006(8)
C7 0.0099(11) 0.0212(12) 0.0142(11) -0.0032(9) 0.0035(9) -0.0023(9)
C4 0.0129(12) 0.0122(10) 0.0125(10) 0.0000(8) 0.0041(9) -0.0001(9)
C1 0.0120(11) 0.0143(11) 0.0124(10) -0.0039(9) 0.0034(8) -0.0012(9)

_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 O2 1.999(2) 1_545 ?
Fe1 O1 2.047(3) 3_656 ?
Fe1 O4 2.125(2) . ?
Fe1 O5 2.141(2) . ?
Fe1 N2 2.144(2) 3_556 ?
O4 C8 1.266(3) . ?
O3 C8 1.252(3) . ?
O5 H5A 0.9500 . ?
O5 H5B 0.9500 . ?
O2 C9 1.258(3) . ?
O2 Fe1 1.999(2) 1_565 ?
O1 C9 1.270(3) . ?
O1 Fe1 2.047(3) 3_656 ?
N2 C7 1.323(3) . ?
N2 C5 1.410(3) . ?
N2 Fe1 2.144(2) 3_556 ?
N1 C7 1.350(3) . ?
N1 C6 1.369(3) . ?
N1 H1B 0.8800 . ?
C3 C4 1.398(3) . ?
C3 C2 1.419(3) . ?
C3 C9 1.500(3) . ?
C5 C4 1.386(3) . ?
C5 C6 1.401(3) . ?
C6 C1 1.393(3) . ?
C8 C2 1.515(3) . ?
C2 C1 1.383(3) . ?
C7 H7A 0.9500 . ?
C4 H4A 0.9500 . ?
C1 H1A 0.9500 . ?

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
O2 Fe1 O1 145.32(7) 1_545 3_656 ?
O2 Fe1 O4 87.67(8) 1_545 . ?
O1 Fe1 O4 86.30(8) 3_656 . ?
O2 Fe1 O5 92.98(9) 1_545 . ?
O1 Fe1 O5 83.55(9) 3_656 . ?
O4 Fe1 O5 163.06(7) . . ?
O2 Fe1 N2 103.58(9) 1_545 3_556 ?
O1 Fe1 N2 110.88(9) 3_656 3_556 ?
O4 Fe1 N2 106.56(8) . 3_556 ?
O5 Fe1 N2 89.75(8) . 3_556 ?
C8 O4 Fe1 134.36(15) . . ?
Fe1 O5 H5A 120.0 . . ?
Fe1 O5 H5B 120.0 . . ?
H5A O5 H5B 120.0 . . ?
C9 O2 Fe1 131.62(18) . 1_565 ?
C9 O1 Fe1 134.90(17) . 3_656 ?
C7 N2 C5 104.72(19) . . ?
C7 N2 Fe1 116.88(16) . 3_556 ?
C5 N2 Fe1 137.88(16) . 3_556 ?
C7 N1 C6 107.1(2) . . ?
C7 N1 H1B 126.4 . . ?
C6 N1 H1B 126.4 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 C9 119.5(2) . . ?
C2 C3 C9 120.0(2) . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 N2 131.9(2) . . ?
C6 C5 N2 108.3(2) . . ?
N1 C6 C1 130.5(2) . . ?
N1 C6 C5 106.5(2) . . ?
C1 C6 C5 123.0(2) . . ?
O2 C9 O1 125.3(2) . . ?
O2 C9 C3 116.7(2) . . ?
O1 C9 C3 118.0(2) . . ?
O3 C8 O4 124.3(2) . . ?
O3 C8 C2 116.7(2) . . ?
O4 C8 C2 118.75(19) . . ?
C1 C2 C3 121.4(2) . . ?
C1 C2 C8 115.1(2) . . ?
C3 C2 C8 123.3(2) . . ?
N2 C7 N1 113.3(2) . . ?
N2 C7 H7A 123.3 . . ?
N1 C7 H7A 123.3 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
C2 C1 C6 116.8(2) . . ?
C2 C1 H1A 121.6 . . ?
C6 C1 H1A 121.6 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.596
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.158
_database_code_depnum_ccdc_archive 'CCDC 930768'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a7
#TrackingRef '7.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Fe N O6'
_chemical_formula_weight         333.08

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   'P -1 '

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

_cell_length_a                   7.292(3)
_cell_length_b                   10.070(4)
_cell_length_c                   10.272(4)
_cell_angle_alpha                113.983(3)
_cell_angle_beta                 99.6830(10)
_cell_angle_gamma                103.652(5)
_cell_volume                     639.4(4)
_cell_formula_units_Z            2
_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          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    1.208
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7038
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2907
_reflns_number_gt                2645
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2907
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.40800(4) 0.62134(3) 0.12121(3) 0.02024(15) Uani 1 1 d . . .
O4 O 1.3872(2) 0.82953(18) 1.13638(19) 0.0251(4) Uani 1 1 d . . .
N1 N 0.6427(3) 0.7340(2) 0.3243(2) 0.0213(4) Uani 1 1 d . . .
O3 O 1.1840(3) 0.62668(18) 0.93183(19) 0.0285(4) Uani 1 1 d . . .
C6 C 1.0519(3) 0.9235(2) 0.7576(2) 0.0184(4) Uani 1 1 d . . .
C8 C 1.2615(3) 0.7712(2) 1.0108(3) 0.0201(4) Uani 1 1 d . . .
C3 C 1.2958(3) 1.0378(2) 1.0478(2) 0.0184(4) Uani 1 1 d . . .
H9A H 1.3766 1.0768 1.1482 0.022 Uiso 1 1 d R . .
C7 C 1.1382(3) 1.0822(2) 0.8512(2) 0.0200(4) Uani 1 1 d . . .
H10A H 1.1125 1.1528 0.8159 0.024 Uiso 1 1 d R . .
C5 C 1.0943(3) 0.8222(2) 0.8098(2) 0.0198(4) Uani 1 1 d . . .
H13A H 1.0410 0.7139 0.7460 0.024 Uiso 1 1 calc R . .
C2 C 1.2596(3) 1.1392(2) 0.9951(2) 0.0179(4) Uani 1 1 d . . .
C4 C 1.2135(3) 0.8791(2) 0.9541(2) 0.0171(4) Uani 1 1 d . . .
C11 C 0.7690(3) 0.6659(3) 0.3520(2) 0.0252(5) Uani 1 1 d . . .
H18A H 0.7646 0.5713 0.2723 0.030 Uiso 1 1 d R . .
C12 C 0.6565(4) 0.8698(3) 0.4361(3) 0.0286(5) Uani 1 1 d . . .
H19A H 0.5716 0.9231 0.4154 0.034 Uiso 1 1 d R . .
C13 C 0.7878(4) 0.9357(3) 0.5764(3) 0.0276(5) Uani 1 1 d . . .
H3A H 0.7911 1.0309 0.6522 0.033 Uiso 1 1 calc R . .
C10 C 0.9054(3) 0.7249(3) 0.4892(3) 0.0251(5) Uani 1 1 d . . .
H2A H 0.9925 0.6719 0.5037 0.030 Uiso 1 1 calc R . .
C9 C 0.9155(3) 0.8620(2) 0.6065(2) 0.0195(4) Uani 1 1 d . . .
O2 O 1.4020(3) 1.36160(19) 1.23196(19) 0.0348(4) Uani 1 1 d . . .
O6 O 0.1840(3) 0.6010(2) 0.2286(2) 0.0368(4) Uani 1 1 d . . .
H6A H 0.2184 0.6379 0.3283 0.044 Uiso 1 1 d R . .
H6B H 0.0556 0.5561 0.1746 0.044 Uiso 1 1 d R . .
C1 C 1.3548(3) 1.3099(2) 1.0951(3) 0.0211(4) Uani 1 1 d . . .
O5 O 0.3267(4) 0.5896(4) 0.4877(3) 0.0746(8) Uani 1 1 d . . .
H5A H 0.2083 0.5819 0.5045 0.090 Uiso 1 1 d R . .
H5B H 0.4268 0.5901 0.5527 0.090 Uiso 1 1 d R . .
O1 O 1.3813(3) 1.39411(18) 1.02770(18) 0.0241(4) 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
Fe1 0.0260(2) 0.0134(2) 0.0172(2) 0.00634(15) -0.00079(14) 0.00625(14)
O4 0.0301(8) 0.0193(8) 0.0230(9) 0.0108(7) -0.0023(7) 0.0086(7)
N1 0.0230(9) 0.0211(9) 0.0149(9) 0.0069(7) -0.0001(7) 0.0060(7)
O3 0.0376(9) 0.0155(8) 0.0279(9) 0.0095(7) 0.0010(7) 0.0083(7)
C6 0.0191(9) 0.0176(10) 0.0156(10) 0.0076(8) 0.0008(8) 0.0045(8)
C8 0.0230(10) 0.0177(10) 0.0222(11) 0.0116(9) 0.0044(8) 0.0084(8)
C3 0.0204(9) 0.0169(10) 0.0153(10) 0.0078(8) 0.0012(8) 0.0043(8)
C7 0.0229(10) 0.0186(10) 0.0207(11) 0.0120(9) 0.0036(8) 0.0079(8)
C5 0.0220(10) 0.0139(9) 0.0196(11) 0.0062(8) 0.0023(8) 0.0052(8)
C2 0.0191(9) 0.0150(10) 0.0196(10) 0.0089(8) 0.0048(8) 0.0047(8)
C4 0.0181(9) 0.0151(10) 0.0195(10) 0.0101(8) 0.0035(8) 0.0058(8)
C11 0.0304(11) 0.0190(11) 0.0177(11) 0.0027(9) 0.0015(9) 0.0085(9)
C12 0.0342(12) 0.0255(12) 0.0192(11) 0.0046(10) -0.0024(9) 0.0160(10)
C13 0.0367(13) 0.0195(11) 0.0173(11) 0.0013(9) -0.0014(9) 0.0137(10)
C10 0.0269(11) 0.0247(11) 0.0211(11) 0.0080(9) 0.0014(9) 0.0134(9)
C9 0.0220(10) 0.0159(10) 0.0174(10) 0.0079(8) 0.0009(8) 0.0042(8)
O2 0.0547(12) 0.0200(9) 0.0170(8) 0.0062(7) -0.0027(8) 0.0053(8)
O6 0.0306(9) 0.0421(11) 0.0303(10) 0.0152(9) 0.0067(8) 0.0049(8)
C1 0.0220(10) 0.0147(10) 0.0229(11) 0.0084(9) 0.0020(8) 0.0038(8)
O5 0.0739(18) 0.105(2) 0.0663(18) 0.0562(18) 0.0195(15) 0.0376(17)
O1 0.0333(8) 0.0146(7) 0.0225(8) 0.0091(6) 0.0052(7) 0.0062(6)

_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 2.0339(18) 1_444 ?
Fe1 O4 2.0820(18) 1_454 ?
Fe1 N1 2.128(2) . ?
Fe1 O6 2.1353(19) . ?
Fe1 O1 2.3313(18) 2_776 ?
Fe1 O3 2.3480(18) 1_454 ?
O4 C8 1.257(3) . ?
O4 Fe1 2.0820(18) 1_656 ?
N1 C11 1.330(3) . ?
N1 C12 1.348(3) . ?
O3 C8 1.262(3) . ?
O3 Fe1 2.3480(18) 1_656 ?
C6 C7 1.395(3) . ?
C6 C5 1.401(3) . ?
C6 C9 1.480(3) . ?
C8 C4 1.506(3) . ?
C3 C2 1.391(3) . ?
C3 C4 1.393(3) . ?
C7 C2 1.388(3) . ?
C5 C4 1.387(3) . ?
C2 C1 1.502(3) . ?
C11 C10 1.377(3) . ?
C12 C13 1.376(3) . ?
C13 C9 1.389(3) . ?
C10 C9 1.391(3) . ?
O2 C1 1.234(3) . ?
C1 O1 1.296(3) . ?
O1 Fe1 2.0339(18) 1_666 ?
O1 Fe1 2.3313(18) 2_776 ?

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 O4 159.21(7) 1_444 1_454 ?
O1 Fe1 N1 106.51(7) 1_444 . ?
O4 Fe1 N1 92.62(7) 1_454 . ?
O1 Fe1 O6 95.90(7) 1_444 . ?
O4 Fe1 O6 90.85(7) 1_454 . ?
N1 Fe1 O6 93.61(8) . . ?
O1 Fe1 O1 77.04(7) 1_444 2_776 ?
O4 Fe1 O1 93.88(6) 1_454 2_776 ?
N1 Fe1 O1 94.02(8) . 2_776 ?
O6 Fe1 O1 170.82(6) . 2_776 ?
O1 Fe1 O3 101.26(7) 1_444 1_454 ?
O4 Fe1 O3 59.04(6) 1_454 1_454 ?
N1 Fe1 O3 151.55(7) . 1_454 ?
O6 Fe1 O3 89.59(8) . 1_454 ?
O1 Fe1 O3 86.12(7) 2_776 1_454 ?
C8 O4 Fe1 95.84(13) . 1_656 ?
C11 N1 C12 117.2(2) . . ?
C11 N1 Fe1 121.24(15) . . ?
C12 N1 Fe1 121.19(15) . . ?
C8 O3 Fe1 83.63(13) . 1_656 ?
C7 C6 C5 118.8(2) . . ?
C7 C6 C9 121.07(19) . . ?
C5 C6 C9 120.14(19) . . ?
O4 C8 O3 121.2(2) . . ?
O4 C8 C4 117.87(19) . . ?
O3 C8 C4 120.9(2) . . ?
C2 C3 C4 119.6(2) . . ?
C2 C7 C6 120.81(19) . . ?
C4 C5 C6 120.35(19) . . ?
C7 C2 C3 120.04(19) . . ?
C7 C2 C1 120.82(19) . . ?
C3 C2 C1 119.1(2) . . ?
C5 C4 C3 120.38(19) . . ?
C5 C4 C8 120.74(19) . . ?
C3 C4 C8 118.85(19) . . ?
N1 C11 C10 123.1(2) . . ?
N1 C12 C13 123.1(2) . . ?
C12 C13 C9 119.6(2) . . ?
C11 C10 C9 119.9(2) . . ?
C13 C9 C10 117.0(2) . . ?
C13 C9 C6 121.72(19) . . ?
C10 C9 C6 121.25(19) . . ?
O2 C1 O1 124.3(2) . . ?
O2 C1 C2 120.1(2) . . ?
O1 C1 C2 115.58(19) . . ?
C1 O1 Fe1 123.98(14) . 1_666 ?
C1 O1 Fe1 122.77(14) . 2_776 ?
Fe1 O1 Fe1 102.96(7) 1_666 2_776 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.079
_database_code_depnum_ccdc_archive 'CCDC 930769'
