# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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_I
_chemical_name_systematic        ?
_chemical_name_common            M-FcCN_LT
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 Fe N'
_chemical_formula_iupac          ?
_chemical_formula_weight         225.07

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.0855(17)
_cell_length_b                   7.5248(9)
_cell_length_c                   10.2932(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.676(6)
_cell_angle_gamma                90
_cell_volume                     980.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8240
_cell_measurement_theta_min      3.2186
_cell_measurement_theta_max      26.3373
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464

_exptl_absorpt_coefficient_mu    1.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.80

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16941
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_full        26.46
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_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.
;

_reflns_number_total             2012
_reflns_number_gt                1818
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0886
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_number_reflns         2012
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0695P)^2^+0.2059P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.20670(14) 0.8195(2) -0.03243(17) 0.0203(4) Uani d . 1 . .
C C2 0.30350(14) 0.7466(3) 0.04492(17) 0.0213(4) Uani d . 1 . .
H H2 0.3109 0.6618 0.1151 0.026 Uiso calc R 1 . .
C C3 0.38723(14) 0.8232(2) -0.00148(17) 0.0213(4) Uani d . 1 . .
H H3 0.4603 0.7986 0.0326 0.026 Uiso calc R 1 . .
C C4 0.34270(15) 0.9426(3) -0.10742(17) 0.0209(4) Uani d . 1 . .
H H4 0.3808 1.0121 -0.1563 0.025 Uiso calc R 1 . .
C C5 0.23152(15) 0.9402(3) -0.12768(17) 0.0211(4) Uani d . 1 . .
H H5 0.1821 1.0069 -0.193 0.025 Uiso calc R 1 . .
C C6 0.22378(16) 1.1471(3) 0.18411(19) 0.0292(4) Uani d . 1 . .
H H6 0.1545 1.1219 0.1921 0.035 Uiso calc R 1 . .
C C7 0.31832(19) 1.0716(3) 0.26254(19) 0.0323(5) Uani d . 1 . .
H H7 0.3238 0.9868 0.3323 0.039 Uiso calc R 1 . .
C C8 0.40387(16) 1.1456(3) 0.2181(2) 0.0328(5) Uani d . 1 . .
H H8 0.4766 1.1191 0.2533 0.039 Uiso calc R 1 . .
C C9 0.36107(16) 1.2657(3) 0.1122(2) 0.0291(5) Uani d . 1 . .
H H9 0.4002 1.3336 0.0637 0.035 Uiso calc R 1 . .
C C10 0.25045(17) 1.2669(2) 0.09146(19) 0.0277(4) Uani d . 1 . .
H H10 0.2021 1.3359 0.0266 0.033 Uiso calc R 1 . .
C C11 0.09722(15) 0.7756(3) -0.0205(2) 0.0285(4) Uani d . 1 . .
H H11A 0.1 0.7439 0.0737 0.034 Uiso calc R 1 . .
H H11B 0.0512 0.8812 -0.0448 0.034 Uiso calc R 1 . .
C C12 0.05237(15) 0.6266(3) -0.1091(2) 0.0281(4) Uani d . 1 . .
Fe Fe1 0.302621(19) 1.01620(3) 0.06453(2) 0.01603(13) Uani d . 1 . .
N N1 0.01991(17) 0.5091(2) -0.1782(2) 0.0376(5) Uani d . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0232(10) 0.0173(9) 0.0206(8) -0.0028(7) 0.0060(7) -0.0042(7)
C2 0.0314(11) 0.0128(9) 0.0191(8) 0.0002(7) 0.0055(8) -0.0025(7)
C3 0.0218(9) 0.0193(9) 0.0219(8) 0.0003(7) 0.0039(7) -0.0086(7)
C4 0.0276(10) 0.0203(9) 0.0154(8) -0.0057(8) 0.0069(7) -0.0061(7)
C5 0.0276(10) 0.0176(8) 0.0160(8) -0.0014(8) 0.0019(7) -0.0010(7)
C6 0.0340(11) 0.0253(10) 0.0331(10) -0.0037(9) 0.0169(9) -0.0115(9)
C7 0.0591(15) 0.0223(10) 0.0160(9) 0.0032(10) 0.0107(9) -0.0050(8)
C8 0.0292(11) 0.0344(11) 0.0301(10) 0.0019(9) -0.0011(8) -0.0194(9)
C9 0.0399(13) 0.0192(9) 0.0318(10) -0.0109(8) 0.0161(9) -0.0126(8)
C10 0.0380(12) 0.0173(9) 0.0266(10) 0.0075(8) 0.0059(8) -0.0053(8)
C11 0.0248(10) 0.0281(10) 0.0340(10) -0.0049(8) 0.0102(8) -0.0065(8)
C12 0.0193(10) 0.0291(11) 0.0366(11) -0.0015(8) 0.0083(8) -0.0002(9)
Fe1 0.0207(2) 0.01327(18) 0.01390(19) -0.00022(9) 0.00400(13) -0.00114(8)
N1 0.0266(11) 0.0381(11) 0.0461(13) -0.0072(7) 0.0054(9) -0.0104(8)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.424(3) ?
C1 C5 . 1.433(2) ?
C1 C11 . 1.505(2) ?
C1 Fe1 . 2.0319(18) ?
C2 C3 . 1.423(3) ?
C2 Fe1 . 2.0394(19) ?
C2 H2 . 0.95 ?
C3 C4 . 1.419(3) ?
C3 Fe1 . 2.0440(17) ?
C3 H3 . 0.95 ?
C4 C5 . 1.417(3) ?
C4 Fe1 . 2.0457(17) ?
C4 H4 . 0.95 ?
C5 Fe1 . 2.0432(18) ?
C5 H5 . 0.95 ?
C6 C7 . 1.414(3) ?
C6 C10 . 1.419(3) ?
C6 Fe1 . 2.0475(18) ?
C6 H6 . 0.95 ?
C7 C8 . 1.425(3) ?
C7 Fe1 . 2.0391(18) ?
C7 H7 . 0.95 ?
C8 C9 . 1.418(3) ?
C8 Fe1 . 2.0351(19) ?
C8 H8 . 0.95 ?
C9 C10 . 1.409(3) ?
C9 Fe1 . 2.0397(19) ?
C9 H9 . 0.95 ?
C10 Fe1 . 2.0485(19) ?
C10 H10 . 0.95 ?
C11 C12 . 1.470(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 N1 . 1.147(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C5 . . 107.64(16) ?
C2 C1 C11 . . 126.86(17) ?
C5 C1 C11 . . 125.48(17) ?
C2 C1 Fe1 . . 69.81(10) ?
C5 C1 Fe1 . . 69.84(10) ?
C11 C1 Fe1 . . 127.02(13) ?
C1 C2 C3 . . 107.91(16) ?
C1 C2 Fe1 . . 69.24(10) ?
C3 C2 Fe1 . . 69.77(10) ?
C1 C2 H2 . . 126.0 ?
C3 C2 H2 . . 126.0 ?
Fe1 C2 H2 . . 126.5 ?
C4 C3 C2 . . 108.26(16) ?
C4 C3 Fe1 . . 69.76(10) ?
C2 C3 Fe1 . . 69.42(10) ?
C4 C3 H3 . . 125.9 ?
C2 C3 H3 . . 125.9 ?
Fe1 C3 H3 . . 126.5 ?
C5 C4 C3 . . 108.13(16) ?
C5 C4 Fe1 . . 69.63(10) ?
C3 C4 Fe1 . . 69.63(10) ?
C5 C4 H4 . . 125.9 ?
C3 C4 H4 . . 125.9 ?
Fe1 C4 H4 . . 126.4 ?
C4 C5 C1 . . 108.06(16) ?
C4 C5 Fe1 . . 69.82(10) ?
C1 C5 Fe1 . . 68.99(10) ?
C4 C5 H5 . . 126.0 ?
C1 C5 H5 . . 126.0 ?
Fe1 C5 H5 . . 126.8 ?
C7 C6 C10 . . 108.08(18) ?
C7 C6 Fe1 . . 69.44(11) ?
C10 C6 Fe1 . . 69.77(10) ?
C7 C6 H6 . . 126.0 ?
C10 C6 H6 . . 126.0 ?
Fe1 C6 H6 . . 126.4 ?
C6 C7 C8 . . 107.75(18) ?
C6 C7 Fe1 . . 70.08(11) ?
C8 C7 Fe1 . . 69.37(11) ?
C6 C7 H7 . . 126.1 ?
C8 C7 H7 . . 126.1 ?
Fe1 C7 H7 . . 126.0 ?
C9 C8 C7 . . 107.83(18) ?
C9 C8 Fe1 . . 69.81(11) ?
C7 C8 Fe1 . . 69.68(11) ?
C9 C8 H8 . . 126.1 ?
C7 C8 H8 . . 126.1 ?
Fe1 C8 H8 . . 126.0 ?
C10 C9 C8 . . 108.13(17) ?
C10 C9 Fe1 . . 70.18(11) ?
C8 C9 Fe1 . . 69.47(11) ?
C10 C9 H9 . . 125.9 ?
C8 C9 H9 . . 125.9 ?
Fe1 C9 H9 . . 126.0 ?
C9 C10 C6 . . 108.21(18) ?
C9 C10 Fe1 . . 69.51(11) ?
C6 C10 Fe1 . . 69.70(11) ?
C9 C10 H10 . . 125.9 ?
C6 C10 H10 . . 125.9 ?
Fe1 C10 H10 . . 126.5 ?
C12 C11 C1 . . 110.81(15) ?
C12 C11 H11A . . 109.5 ?
C1 C11 H11A . . 109.5 ?
C12 C11 H11B . . 109.5 ?
C1 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
N1 C12 C11 . . 178.3(2) ?
C1 Fe1 C8 . . 158.39(9) ?
C1 Fe1 C7 . . 122.22(8) ?
C8 Fe1 C7 . . 40.95(9) ?
C1 Fe1 C9 . . 159.42(8) ?
C8 Fe1 C9 . . 40.72(9) ?
C7 Fe1 C9 . . 68.56(8) ?
C1 Fe1 C2 . . 40.95(7) ?
C8 Fe1 C2 . . 122.27(8) ?
C7 Fe1 C2 . . 107.50(8) ?
C9 Fe1 C2 . . 158.19(8) ?
C1 Fe1 C5 . . 41.17(7) ?
C8 Fe1 C5 . . 158.97(9) ?
C7 Fe1 C5 . . 158.59(9) ?
C9 Fe1 C5 . . 122.81(8) ?
C2 Fe1 C5 . . 68.78(7) ?
C1 Fe1 C3 . . 68.79(7) ?
C8 Fe1 C3 . . 107.30(8) ?
C7 Fe1 C3 . . 123.48(8) ?
C9 Fe1 C3 . . 122.17(8) ?
C2 Fe1 C3 . . 40.80(7) ?
C5 Fe1 C3 . . 68.36(7) ?
C1 Fe1 C4 . . 68.88(7) ?
C8 Fe1 C4 . . 122.86(8) ?
C7 Fe1 C4 . . 159.58(9) ?
C9 Fe1 C4 . . 107.14(8) ?
C2 Fe1 C4 . . 68.65(7) ?
C5 Fe1 C4 . . 40.54(8) ?
C3 Fe1 C4 . . 40.61(7) ?
C1 Fe1 C6 . . 107.64(8) ?
C8 Fe1 C6 . . 68.34(8) ?
C7 Fe1 C6 . . 40.48(8) ?
C9 Fe1 C6 . . 68.16(8) ?
C2 Fe1 C6 . . 123.66(8) ?
C5 Fe1 C6 . . 122.79(8) ?
C3 Fe1 C6 . . 159.95(8) ?
C4 Fe1 C6 . . 158.27(8) ?
C1 Fe1 C10 . . 123.49(8) ?
C8 Fe1 C10 . . 68.17(8) ?
C7 Fe1 C10 . . 68.23(8) ?
C9 Fe1 C10 . . 40.31(9) ?
C2 Fe1 C10 . . 160.03(8) ?
C5 Fe1 C10 . . 107.66(8) ?
C3 Fe1 C10 . . 157.88(8) ?
C4 Fe1 C10 . . 122.25(8) ?
C6 Fe1 C10 . . 40.53(8) ?

_database_code_depnum_ccdc_archive 'CCDC 942724'
#######################################################################
#
#                 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_I
_chemical_name_systematic        ?
_chemical_name_common            Morada
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 Fe N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         239.05
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.612(6)
_cell_length_b                   10.349(9)
_cell_length_c                   13.003(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1024.3(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1860
_cell_measurement_theta_min      3.1010
_cell_measurement_theta_max      23.5831
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'dark purple'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488

_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5228
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0823
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15

_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.
;

_reflns_number_total             1877
_reflns_number_gt                1426
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1412
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_number_reflns         1877
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.691
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.54(6)

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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C9 0.0562(16) 0.7219(6) 0.1310(5) 0.113(4) Uani d G 1 . .
H H9 0.1101 0.7822 0.0884 0.136 Uiso calc R 1 . .
C C10 -0.1246(14) 0.6880(8) 0.1299(5) 0.107(4) Uani d G 1 . .
H H10 -0.2098 0.7222 0.0865 0.128 Uiso calc R 1 . .
C C6 -0.1523(8) 0.5925(8) 0.2066(7) 0.098(4) Uani d G 1 . .
H H6 -0.2589 0.5533 0.2224 0.117 Uiso calc R 1 . .
C C7 0.0113(13) 0.5674(6) 0.2552(4) 0.085(3) Uani d G 1 . .
H H7 0.0306 0.5089 0.3083 0.102 Uiso calc R 1 . .
C C8 0.1402(8) 0.6474(9) 0.2084(7) 0.092(3) Uani d G 1 . .
H H8 0.2587 0.6504 0.2255 0.11 Uiso calc R 1 . .
C C1 0.2084(8) 0.4214(7) 0.0284(5) 0.0441(15) Uani d . 1 . .
C C2 0.1104(10) 0.4929(7) -0.0451(5) 0.056(2) Uani d . 1 . .
H H2 0.1573 0.5519 -0.0916 0.067 Uiso calc R 1 . .
C C3 -0.0640(10) 0.4616(10) -0.0368(6) 0.068(2) Uani d . 1 . .
H H3 -0.1553 0.4959 -0.0757 0.082 Uiso calc R 1 . .
C C4 -0.0801(9) 0.3640(8) 0.0445(7) 0.066(2) Uani d . 1 . .
H H4 -0.1832 0.324 0.066 0.079 Uiso calc R 1 . .
C C5 0.0877(8) 0.3425(6) 0.0836(5) 0.0483(16) Uani d . 1 . .
H H5 0.1161 0.2861 0.1368 0.058 Uiso calc R 1 . .
C C11 0.3862(10) 0.4437(7) 0.0558(5) 0.0523(18) Uani d . 1 . .
C C12 0.4461(9) 0.3770(8) 0.1545(6) 0.063(2) Uani d . 1 . .
Fe Fe1 0.02493(11) 0.53015(8) 0.10058(6) 0.0396(3) Uani d . 1 . .
N N1 0.4979(10) 0.3318(8) 0.2270(5) 0.089(2) Uani d . 1 . .
O O1 0.4924(6) 0.5066(5) 0.0101(4) 0.0762(15) Uani d . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C9 0.209(13) 0.029(4) 0.101(8) -0.016(6) 0.067(9) -0.017(4)
C10 0.163(11) 0.095(9) 0.063(6) 0.080(9) -0.014(7) -0.021(6)
C6 0.084(7) 0.111(9) 0.098(7) -0.008(6) 0.033(6) -0.072(7)
C7 0.139(9) 0.066(6) 0.050(4) 0.013(7) -0.004(5) -0.022(4)
C8 0.071(6) 0.086(8) 0.119(8) -0.008(5) 0.005(6) -0.072(7)
C1 0.042(4) 0.044(4) 0.047(4) 0.003(3) 0.006(3) -0.002(3)
C2 0.071(5) 0.059(6) 0.038(3) 0.004(4) 0.006(3) -0.003(3)
C3 0.064(5) 0.084(5) 0.057(4) 0.002(5) -0.012(3) -0.024(5)
C4 0.048(5) 0.063(5) 0.086(5) -0.008(4) -0.001(4) -0.038(5)
C5 0.056(4) 0.028(3) 0.062(4) 0.002(3) 0.007(4) -0.006(3)
C11 0.051(4) 0.051(5) 0.055(4) -0.003(3) 0.007(3) -0.006(3)
C12 0.047(4) 0.069(5) 0.073(5) 0.008(4) 0.001(4) -0.001(4)
Fe1 0.0450(5) 0.0320(4) 0.0417(4) 0.0031(4) -0.0022(4) -0.0041(4)
N1 0.078(5) 0.106(6) 0.082(4) 0.019(5) -0.015(5) 0.019(4)
O1 0.055(3) 0.086(4) 0.087(3) -0.008(3) 0.019(3) 0.010(3)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C9 C8 . 1.42 ?
C9 C10 . 1.42 ?
C9 Fe1 . 2.037(6) ?
C9 H9 . 0.93 ?
C10 C6 . 1.42 ?
C10 Fe1 . 2.027(6) ?
C10 H10 . 0.93 ?
C6 C7 . 1.42 ?
C6 Fe1 . 2.034(6) ?
C6 H6 . 0.93 ?
C7 C8 . 1.42 ?
C7 Fe1 . 2.049(5) ?
C7 H7 . 0.93 ?
C8 Fe1 . 2.051(6) ?
C8 H8 . 0.93 ?
C1 C11 . 1.418(9) ?
C1 C2 . 1.421(9) ?
C1 C5 . 1.423(9) ?
C1 Fe1 . 2.024(6) ?
C2 C3 . 1.371(10) ?
C2 Fe1 . 2.039(6) ?
C2 H2 . 0.93 ?
C3 C4 . 1.468(12) ?
C3 Fe1 . 2.038(7) ?
C3 H3 . 0.93 ?
C4 C5 . 1.393(10) ?
C4 Fe1 . 2.032(7) ?
C4 H4 . 0.93 ?
C5 Fe1 . 2.012(6) ?
C5 H5 . 0.93 ?
C11 O1 . 1.195(8) ?
C11 C12 . 1.528(10) ?
C12 N1 . 1.123(9) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 C9 C10 . . 108.0 ?
C8 C9 Fe1 . . 70.2(2) ?
C10 C9 Fe1 . . 69.2(2) ?
C8 C9 H9 . . 126.0 ?
C10 C9 H9 . . 126.0 ?
Fe1 C9 H9 . . 126.2 ?
C9 C10 C6 . . 108.0 ?
C9 C10 Fe1 . . 69.9(2) ?
C6 C10 Fe1 . . 69.8(2) ?
C9 C10 H10 . . 126.0 ?
C6 C10 H10 . . 126.0 ?
Fe1 C10 H10 . . 125.8 ?
C7 C6 C10 . . 108.0 ?
C7 C6 Fe1 . . 70.2(2) ?
C10 C6 Fe1 . . 69.2(2) ?
C7 C6 H6 . . 126.0 ?
C10 C6 H6 . . 126.0 ?
Fe1 C6 H6 . . 126.1 ?
C6 C7 C8 . . 108.0 ?
C6 C7 Fe1 . . 69.1(2) ?
C8 C7 Fe1 . . 69.8(2) ?
C6 C7 H7 . . 126.0 ?
C8 C7 H7 . . 126.0 ?
Fe1 C7 H7 . . 126.7 ?
C9 C8 C7 . . 108.0 ?
C9 C8 Fe1 . . 69.1(2) ?
C7 C8 Fe1 . . 69.7(2) ?
C9 C8 H8 . . 126.0 ?
C7 C8 H8 . . 126.0 ?
Fe1 C8 H8 . . 126.7 ?
C11 C1 C2 . . 125.8(7) ?
C11 C1 C5 . . 125.7(6) ?
C2 C1 C5 . . 107.4(6) ?
C11 C1 Fe1 . . 116.9(5) ?
C2 C1 Fe1 . . 70.1(4) ?
C5 C1 Fe1 . . 68.9(3) ?
C3 C2 C1 . . 109.4(7) ?
C3 C2 Fe1 . . 70.3(4) ?
C1 C2 Fe1 . . 69.0(3) ?
C3 C2 H2 . . 125.3 ?
C1 C2 H2 . . 125.3 ?
Fe1 C2 H2 . . 127.0 ?
C2 C3 C4 . . 107.5(7) ?
C2 C3 Fe1 . . 70.4(4) ?
C4 C3 Fe1 . . 68.6(4) ?
C2 C3 H3 . . 126.3 ?
C4 C3 H3 . . 126.3 ?
Fe1 C3 H3 . . 126.3 ?
C5 C4 C3 . . 107.2(7) ?
C5 C4 Fe1 . . 69.1(4) ?
C3 C4 Fe1 . . 69.1(4) ?
C5 C4 H4 . . 126.4 ?
C3 C4 H4 . . 126.4 ?
Fe1 C4 H4 . . 127.0 ?
C4 C5 C1 . . 108.5(6) ?
C4 C5 Fe1 . . 70.6(4) ?
C1 C5 Fe1 . . 69.8(4) ?
C4 C5 H5 . . 125.8 ?
C1 C5 H5 . . 125.8 ?
Fe1 C5 H5 . . 125.4 ?
O1 C11 C1 . . 127.6(7) ?
O1 C11 C12 . . 117.5(7) ?
C1 C11 C12 . . 114.9(6) ?
N1 C12 C11 . . 176.4(9) ?
C5 Fe1 C1 . . 41.3(3) ?
C5 Fe1 C10 . . 158.7(4) ?
C1 Fe1 C10 . . 157.3(4) ?
C5 Fe1 C4 . . 40.3(3) ?
C1 Fe1 C4 . . 68.6(3) ?
C10 Fe1 C4 . . 121.9(4) ?
C5 Fe1 C6 . . 122.6(3) ?
C1 Fe1 C6 . . 161.5(3) ?
C10 Fe1 C6 . . 40.93(11) ?
C4 Fe1 C6 . . 104.5(3) ?
C5 Fe1 C3 . . 69.3(3) ?
C1 Fe1 C3 . . 68.2(3) ?
C10 Fe1 C3 . . 105.0(3) ?
C4 Fe1 C3 . . 42.3(3) ?
C6 Fe1 C3 . . 119.0(3) ?
C5 Fe1 C9 . . 159.0(4) ?
C1 Fe1 C9 . . 123.4(3) ?
C10 Fe1 C9 . . 40.91(11) ?
C4 Fe1 C9 . . 160.0(4) ?
C6 Fe1 C9 . . 68.71(12) ?
C3 Fe1 C9 . . 123.2(4) ?
C5 Fe1 C2 . . 68.9(3) ?
C1 Fe1 C2 . . 40.9(3) ?
C10 Fe1 C2 . . 120.4(3) ?
C4 Fe1 C2 . . 68.4(3) ?
C6 Fe1 C2 . . 154.3(3) ?
C3 Fe1 C2 . . 39.3(3) ?
C9 Fe1 C2 . . 109.1(3) ?
C5 Fe1 C7 . . 107.5(3) ?
C1 Fe1 C7 . . 126.5(3) ?
C10 Fe1 C7 . . 68.62(12) ?
C4 Fe1 C7 . . 119.4(3) ?
C6 Fe1 C7 . . 40.69(10) ?
C3 Fe1 C7 . . 155.3(3) ?
C9 Fe1 C7 . . 68.43(12) ?
C2 Fe1 C7 . . 164.3(3) ?
C5 Fe1 C8 . . 123.0(3) ?
C1 Fe1 C8 . . 110.5(3) ?
C10 Fe1 C8 . . 68.59(13) ?
C4 Fe1 C8 . . 156.1(4) ?
C6 Fe1 C8 . . 68.44(12) ?
C3 Fe1 C8 . . 161.3(4) ?
C9 Fe1 C8 . . 40.65(11) ?
C2 Fe1 C8 . . 127.6(3) ?
C7 Fe1 C8 . . 40.52(9) ?

_database_code_depnum_ccdc_archive 'CCDC 942725'