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


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 892309'
#TrackingRef '12621_web_deposit_cif_file_0_Yan-ZhenZheng_1342454409.fem.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 Fe O5'
_chemical_formula_weight         243.02

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/m

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

_cell_length_a                   8.010(2)
_cell_length_b                   6.8872(18)
_cell_length_c                   8.569(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.232(5)
_cell_angle_gamma                90.00
_cell_volume                     449.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             250
_exptl_absorpt_coefficient_mu    1.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5924
_exptl_absorpt_correction_T_max  0.9516
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2447
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         26.98
_reflns_number_total             1054
_reflns_number_gt                880
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0429P)^2^+0.6366P] 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         1054
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Fe1 Fe 0.5000 0.5000 0.5000 0.01192(18) Uani 1 2 d S . .
O1H O 0.6174(4) 0.7500 0.5634(4) 0.0157(6) Uani 1 2 d S . .
H1 H 0.666(8) 0.7500 0.640(7) 0.04(2) Uiso 1 2 d S . .
O1 O 0.7092(3) 0.4113(3) 0.4358(3) 0.0250(5) Uani 1 1 d . . .
O2 O 0.6171(3) 0.4115(3) -0.2671(2) 0.0262(5) Uani 1 1 d . . .
C1 C 0.7652(5) 0.2500 0.4066(4) 0.0137(8) Uani 1 2 d S . .
C2 C 0.9188(5) 0.2500 0.3373(5) 0.0158(8) Uani 1 2 d S . .
H2A H 1.0277 0.2500 0.4323 0.019 Uiso 1 2 calc SR . .
C3 C 0.9236(4) 0.4335(4) 0.2371(3) 0.0190(6) Uani 1 1 d . . .
H3A H 0.9101 0.5481 0.2999 0.023 Uiso 1 1 calc R . .
H3B H 1.0381 0.4424 0.2187 0.023 Uiso 1 1 calc R . .
C4 C 0.7783(4) 0.4327(5) 0.0715(3) 0.0229(7) Uani 1 1 d . . .
H4A H 0.6635 0.4390 0.0895 0.028 Uiso 1 1 calc R . .
H4B H 0.7902 0.5474 0.0082 0.028 Uiso 1 1 calc R . .
C5 C 0.7881(6) 0.2500 -0.0253(5) 0.0214(9) Uani 1 2 d S . .
H5A H 0.9071 0.2500 -0.0373 0.026 Uiso 1 2 calc SR . .
C6 C 0.6603(5) 0.2500 -0.1995(5) 0.0178(9) Uani 1 2 d S . .

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 0.0149(3) 0.0083(3) 0.0114(3) 0.0001(2) 0.00249(19) 0.0009(2)
O1H 0.0148(14) 0.0099(13) 0.0186(16) 0.000 -0.0005(13) 0.000
O1 0.0223(11) 0.0164(11) 0.0415(13) -0.0070(10) 0.0173(10) -0.0021(9)
O2 0.0401(13) 0.0158(11) 0.0140(10) 0.0035(9) -0.0039(9) -0.0023(10)
C1 0.0140(18) 0.0164(19) 0.0089(17) 0.000 0.0011(15) 0.000
C2 0.0118(18) 0.019(2) 0.0149(18) 0.000 0.0022(15) 0.000
C3 0.0220(14) 0.0209(14) 0.0138(13) -0.0031(11) 0.0050(11) -0.0076(12)
C4 0.0339(17) 0.0166(13) 0.0149(13) 0.0012(11) 0.0029(12) -0.0021(13)
C5 0.024(2) 0.020(2) 0.015(2) 0.000 -0.0008(17) 0.000
C6 0.021(2) 0.018(2) 0.0130(19) 0.000 0.0036(17) 0.000

_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 O1H 1.9555(15) 3_666 ?
Fe1 O1H 1.9555(15) . ?
Fe1 O1 2.015(2) . ?
Fe1 O1 2.015(2) 3_666 ?
Fe1 O2 2.0154(19) 3_665 ?
Fe1 O2 2.0154(19) 1_556 ?
O1H Fe1 1.9555(15) 2_656 ?
O1H H1 0.65(5) . ?
O1 C1 1.252(3) . ?
O2 C6 1.252(3) . ?
O2 Fe1 2.0154(19) 1_554 ?
C1 O1 1.252(3) 4_565 ?
C1 C2 1.525(5) . ?
C2 C3 1.535(4) 4_565 ?
C2 C3 1.535(4) . ?
C2 H2A 0.9900 . ?
C3 C4 1.528(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C5 1.523(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C4 1.523(4) 4_565 ?
C5 C6 1.523(5) . ?
C5 H5A 0.9900 . ?
C6 O2 1.252(3) 4_565 ?

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
O1H Fe1 O1H 180.0 3_666 . ?
O1H Fe1 O1 91.49(10) 3_666 . ?
O1H Fe1 O1 88.51(11) . . ?
O1H Fe1 O1 88.51(11) 3_666 3_666 ?
O1H Fe1 O1 91.49(10) . 3_666 ?
O1 Fe1 O1 180.000(1) . 3_666 ?
O1H Fe1 O2 87.52(11) 3_666 3_665 ?
O1H Fe1 O2 92.48(11) . 3_665 ?
O1 Fe1 O2 89.45(9) . 3_665 ?
O1 Fe1 O2 90.55(9) 3_666 3_665 ?
O1H Fe1 O2 92.48(11) 3_666 1_556 ?
O1H Fe1 O2 87.52(11) . 1_556 ?
O1 Fe1 O2 90.55(9) . 1_556 ?
O1 Fe1 O2 89.45(9) 3_666 1_556 ?
O2 Fe1 O2 180.0 3_665 1_556 ?
Fe1 O1H Fe1 123.41(16) . 2_656 ?
Fe1 O1H H1 111.4(18) . . ?
Fe1 O1H H1 111.4(18) 2_656 . ?
C1 O1 Fe1 134.7(2) . . ?
C6 O2 Fe1 134.6(2) . 1_554 ?
O1 C1 O1 125.1(4) 4_565 . ?
O1 C1 C2 117.42(18) 4_565 . ?
O1 C1 C2 117.42(18) . . ?
C1 C2 C3 112.5(2) . 4_565 ?
C1 C2 C3 112.5(2) . . ?
C3 C2 C3 110.9(3) 4_565 . ?
C1 C2 H2A 106.9 . . ?
C3 C2 H2A 106.9 4_565 . ?
C3 C2 H2A 106.9 . . ?
C4 C3 C2 111.8(3) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 110.8(3) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C4 111.4(3) . 4_565 ?
C4 C5 C6 113.6(2) . . ?
C4 C5 C6 113.6(2) 4_565 . ?
C4 C5 H5A 105.8 . . ?
C4 C5 H5A 105.8 4_565 . ?
C6 C5 H5A 105.8 . . ?
O2 C6 O2 125.4(4) 4_565 . ?
O2 C6 C5 117.21(18) 4_565 . ?
O2 C6 C5 117.21(18) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.98
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.094